Chemical context   {#sec1}
==================

Non-covalent inter­actions, such as hydrogen, aerogen, halogen, chalcogen, pnicogen, tetrel and icosa­gen bonds, as well as *n*--π\*, π--π stacking, π--cation, π--anion and hydro­phobic inter­actions, have an impact on the synthesis, catalysis and design of materials and on biological processes (Shikhaliyev *et al.*, 2018[@bb21]; Hazra *et al.*, 2018[@bb10]). These weak forces can also control or organize the aggregation, conformation, tertiary and quaternary structure of a mol­ecule, and its stabilization or other particular properties (Legon, 2017[@bb12]; Mahmudov *et al.*, 2017*a* [@bb14],*b* [@bb15]). In comparison with well-established hydrogen and halogen bonds (Cavallo *et al.*, 2016[@bb6]; Mahmoudi *et al.*, 2018[@bb13]; Vandyshev *et al.*, 2017[@bb23]), chalcogen, pnicogen, tetrel and icosa­gen bonds are much less explored (Mahmudov *et al.*, 2017*a* [@bb14]; Scheiner, 2013[@bb18]; Mikherdov *et al.*, 2016[@bb17]).

The title compound, C~18~H~16~F~3~NO~7~, has a 7-oxabi­cyclo\[2.2.1\]heptene scaffold, thus making it a potential tool for the design and synthesis of new organic materials with various useful properties such as electronic materials, molecular tweezers, *etc* (Borisova *et al.*, 2018*a* [@bb1],*b* [@bb2]). During the structure determination, we noted rather unusual intra­molecular O⋯F inter­actions. Here we report the synthesis, mol­ecular and crystal structure of this compound as well as a Hirshfeld surface analysis.

Structural commentary   {#sec2}
=======================

The mol­ecule of the title compound (Fig. 1[▸](#fig1){ref-type="fig"}) is made up from a fused cyclic system containing four five-membered rings (two di­hydro­furan and two tetra­hydro­furan) in the usual envelope conformations and a six-membered piperidine ring in a chair conformation. The latter is distorted because the environment of the N1 atom is inter­mediate between trigonal--planar and trigonal--pyramidal. The puckering parameters of the five-membered di­hydro­furan \[*A* (O1/C1/C2/C5/C6), *B* (O2/C1/C6/C7/C10)\] and tetra­hydro­furan \[*C* (O1/C2--C5), *D* (O2/C7--C10)\] rings are *A*: *Q*(2) = 0.5780 (15) Å, φ(2) = 359.75 (17)°; *B*: *Q*(2) = 0.5737 (16) Å, φ(2) = 4.53 (17)°; *C*: *Q*(2) = 0.5173 (15) Å, φ(2) = 179.60 (19)°; *D*: *Q*(2) = 0.5154 (16) Å, φ(2) = 178.2 (2)°. The puckering parameters of the six-membered piperidine ring (N1/C1/C2/C10--C12) are *Q* ~T~ = 0.5312 (17) Å, θ = 9.58 (18)°, φ = 329.1 (11)°.

The mol­ecular conformations are stabilized by weak intra­molecular C---H⋯O and C---H⋯F inter­actions (Table 1[▸](#table1){ref-type="table"}) between methyl­ene groups (C11; C12) and a meth­oxy group and the --CF~3~ group, respectively. A rather unusual intra­molecular O**⋯**F inter­action between one of the oxygen bridgehead atoms (O1) and one of the F atoms of the --CF~3~ group \[C5---O1⋯F2 = 2.9336 (16) Å; C5---O1⋯F2 = 153.60 (9)°\] might help to consolidate the conformational arrangement.

Supra­molecular features   {#sec3}
==========================

Inter­molecular C---H⋯O inter­actions involving the O atoms of carbonyl groups, the oxygen bridgehead atoms and meth­oxy O atoms, as well as C---H⋯F hydrogen bonds define the crystal packing, which is shown in Fig. 2[▸](#fig2){ref-type="fig"}. These packing features lead to the formation of a three-dimensional network structure. C---H⋯π and π--π inter­actions are not observed, but H⋯H inter­actions dominate in the packing as detailed in the next section.

Hirshfeld surface analysis   {#sec4}
============================

Hirshfeld surface and fingerprint plots were generated using *CrystalExplorer* (McKinnon *et al.*, 2007[@bb16]). Hirshfeld surfaces enable the visualization of inter­molecular inter­actions by different colors and color intensity, representing short or long contacts and indicating the relative strength of the inter­actions. Fig. 3[▸](#fig3){ref-type="fig"} shows the Hirshfeld surface of the title compound mapped over *d* ~norm~ where it is evident from the bright-red spots appearing near the oxygen atoms that these atoms play a significant role in the mol­ecular packing. The red spots represent closer contacts and negative *d* ~norm~ values on the surface, corresponding to the C---H⋯O inter­actions. The percentage contributions of various contacts to the total Hirshfeld surface are given in Table 2[▸](#table2){ref-type="table"} and are also shown as two-dimensional fingerprint plots in Fig. 4[▸](#fig4){ref-type="fig"}. The H⋯H inter­actions appear in the middle of the scattered points in the two-dimensional fingerprint plots with an overall contribution to the Hirshfeld surface of 35.6% (Fig. 4[▸](#fig4){ref-type="fig"} *b*). The contribution from the O⋯H/H⋯O contacts, corresponding to C---H⋯O inter­actions, is represented by a pair of sharp spikes characteristic of a strong hydrogen-bonding inter­action (28.5%; Fig. 4[▸](#fig4){ref-type="fig"} *c*). The contribution of the F⋯H/H⋯F inter­molecular contacts to the Hirshfeld surfaces is 23.8% (Fig. 4[▸](#fig4){ref-type="fig"} *d*). The small percentage contributions from the remaining inter­atomic contacts are summarized in Table 2[▸](#table2){ref-type="table"} and indicated by their fingerprint plots for C⋯H/H⋯C (Fig. 4[▸](#fig4){ref-type="fig"} *e*), F⋯F (Fig. 4[▸](#fig4){ref-type="fig"} *f*), F⋯O/O⋯F (Fig. 4[▸](#fig4){ref-type="fig"} *g*), O⋯O (Fig. 4[▸](#fig4){ref-type="fig"} *h*), N⋯H/H⋯N (Fig. 4[▸](#fig4){ref-type="fig"} *i*) and C⋯O/O⋯C (Fig. 4[▸](#fig4){ref-type="fig"} *j*). The large number of H⋯H, O⋯H/H⋯O and F⋯H/H⋯F inter­actions suggest that van der Waals inter­actions and hydrogen bonding play the major roles in the crystal packing (Hathwar *et al.*, 2015[@bb9]).

Database survey   {#sec5}
=================

A search of the Cambridge Structural Database (Version 5.39; Groom *et al.*, 2016[@bb8]) for similar structures showed the two closest are those of 2-benzyl-6a,9b-bis­(tri­fluoro­meth­yl)-2,3,6a,9b-tetra­hydro-1*H*,6*H*,7*H*-3a,6:7,9a-di­epoxy­benzo\[*de*\]iso­quinoline (CSD refcode HENLAQ; Borisova *et al.*, 2018*c* [@bb3]) and 2-benzyl-4,5-bis­(tri­fluoro­meth­yl)-2,3,6a,9b-tetra­hydro-1*H*,6*H*,7*H*-3a,6:7,9a-di­epoxy­benzo\[*de*\]iso­quinoline (HEN­LEU; Borisova *et al.*, 2018*d* [@bb4]). In the crystal of HENLAQ, inversion-related pairs of mol­ecules are linked into dimers by C---H⋯O hydrogen bonds. These dimers form sheets lying parallel to (100). C---H⋯π inter­actions are also observed in the crystal structure of HENLAQ, together with intra­molecular F⋯F contacts. The asymmetric unit of HENLEU contains two mol­ecules. In the crystal, mol­ecules are linked by C---H⋯O and C---H⋯F hydrogen bonds, forming columns along \[010\]. Likewise, C---H⋯π inter­actions and F⋯F intra­molecular contacts are also present.

Synthesis and crystallization   {#sec6}
===============================

The synthesis of the title compound and its characterization by ^1^H NMR, ^13^C NMR, IR and HRMS spectroscopy have previously been reported (Borisova *et al.*, 2018*a* [@bb1]). Dimethyl acetyl­enedi­carboxyl­ate (DMAD, 1.84 ml, 0.015 mol) was added to a solution of 2,2,2-tri­fluoro-*N*,*N*-bis­(furan-2-yl­meth­yl)acetamide (0.01 mol) in benzene (30 ml). The mixture was heated at reflux for 15.5--40 h at 353 K (GC--MS monitoring until disappearance of the starting material). The reaction mixture was cooled and left overnight at room temperature. The solvent was removed under reduced pressure. The residue (brown oil) was triturated with diethyl ether. The obtained crystals were filtered off and recrystallized from hexa­ne/EtOAc (*v*:*v* = 2:1) to give the pure compound as a white powder (2.57 g, 6.2 mmol, yield 62%). *R* ~f~ = 0.56 (EtOAc/hexane, 2:1, Sorbfil). M.p. 467.2--467.9 K (from hexa­ne/EtOAc). ^1^H NMR (400 MHz, CDCl~3~): δ 6.74--6.71 (2H, *m*, H-4 and H-9), 6.46 (2H, *dd*, *J* = 2.3 and *J* = 5.5 Hz, H-5 and H-8), 5.14 (2H, *br s*, H-6 and H-7), 5.10 (1H, *d*, *J* = 14.9 Hz, H-1A), 4.43 (1H, *br d*, *J* = 14.9 Hz, H-3A), 4.08 (1H, *d*, *J* = 14.9 Hz, H-3B), 3.64 (6H, *s*, 2 × CO~2~Me), 3.59 (1H, *d*, *J* = 14.9, H-1B). ^13^C NMR (100 MHz, CDCl~3~): δ 170.1 (2 × CO~2~Me), 157.2 (*q*, *J* = 35.5 Hz, F3C---C), 141.2 (C-5 and C-8), 137.5 (C-4 and C-9), 116.4 (*q*, *J* = 288.1 Hz, CF~3~), 87.1 (C-3a and C-9a), 83.8 (C-6 and C-7), 71.4 and 68.8 (C-9 and C-6a), 52.4 (2 × CO~2~Me), 44.8 (*q*, *J* = 3.8 Hz, C-1), 42.4 (C-3). ^19^F NMR (282 MHz, CDCl~3~): δ −67.7 (*s*, CF~3~). IR ν~max~/cm^−1^ (KBr): 3109, 3055, 2956, 1713, 1688, 1197. HRMS (ESI--TOF): calculated for C~18~H~16~F~3~NO~7~ \[*M* + H\]^+^, 415.0879; found, 415.0889.

Refinement details   {#sec7}
====================

Crystal data, data collection and structure refinement details are summarized in Table 3[▸](#table3){ref-type="table"}. All H atoms were fixed and allowed to ride on the parent atoms, with C---H = 0.95--1.00 Å, and with *U* ~iso~(H) = 1.5*U* ~eq~(C) for methyl H atoms and 1.2*U* ~eq~(C) for all other H atoms. Eight outliers \[(101), (011), (01), (002), (110), (363), (03), (111)\] were omitted in the final cycles of refinement.

Supplementary Material
======================

Crystal structure: contains datablock(s) I, global. DOI: [10.1107/S2056989018014305/wm5463sup1.cif](https://doi.org/10.1107/S2056989018014305/wm5463sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S2056989018014305/wm5463Isup2.hkl](https://doi.org/10.1107/S2056989018014305/wm5463Isup2.hkl)

CCDC reference: [1872524](http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1872524)

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?wm5463&file=wm5463sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?wm5463sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?wm5463&checkcif=yes)

Crystal data {#d1e147}
============

  ------------------------- ---------------------------------------
  C~18~H~16~F~3~NO~7~       *F*(000) = 856
  *M~r~* = 415.32           *D*~x~ = 1.601 Mg m^−3^
  Monoclinic, *P*2~1~/*n*   Mo *K*α radiation, λ = 0.71073 Å
  *a* = 8.7661 (2) Å        Cell parameters from 3572 reflections
  *b* = 11.2908 (3) Å       θ = 3.0--25.9°
  *c* = 17.5089 (4) Å       µ = 0.14 mm^−1^
  β = 96.021 (1)°           *T* = 150 K
  *V* = 1723.41 (7) Å^3^    Block, colourless
  *Z* = 4                   0.35 × 0.32 × 0.30 mm
  ------------------------- ---------------------------------------

Data collection {#d1e273}
===============

  --------------------------------------------------------------------- --------------------------------------
  Bruker APEXII CCD diffractometer                                      2739 reflections with *I* \> 2σ(*I*)
  φ and ω scans                                                         *R*~int~ = 0.028
  Absorption correction: multi-scan (*SADABS*; Krause *et al.*, 2015)   θ~max~ = 26.4°, θ~min~ = 3.1°
  *T*~min~ = 0.942, *T*~max~ = 0.946                                    *h* = −10→10
  11170 measured reflections                                            *k* = −14→11
  3496 independent reflections                                          *l* = −21→20
  --------------------------------------------------------------------- --------------------------------------

Refinement {#d1e388}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  0 restraints
  Least-squares matrix: full            Hydrogen site location: inferred from neighbouring sites
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.036   H-atom parameters constrained
  *wR*(*F*^2^) = 0.091                  *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0391*P*)^2^ + 0.8462*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.01                            (Δ/σ)~max~ \< 0.001
  3496 reflections                      Δρ~max~ = 0.30 e Å^−3^
  264 parameters                        Δρ~min~ = −0.25 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Special details {#d1e539}
===============

  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#d1e558}
==================================================================================================

  ------ -------------- -------------- -------------- -------------------- --
         *x*            *y*            *z*            *U*~iso~\*/*U*~eq~   
  C1     0.39473 (17)   0.49611 (14)   0.67777 (9)    0.0151 (3)           
  C2     0.34636 (17)   0.36454 (14)   0.65512 (9)    0.0159 (3)           
  C3     0.17517 (18)   0.35392 (15)   0.66061 (10)   0.0188 (4)           
  H3     0.125910       0.313775       0.698918       0.023\*              
  C4     0.10926 (18)   0.41275 (15)   0.60044 (9)    0.0190 (4)           
  H4     0.002414       0.423058       0.586488       0.023\*              
  C5     0.23948 (17)   0.46040 (14)   0.55824 (9)    0.0166 (3)           
  H5     0.211134       0.478143       0.502604       0.020\*              
  C6     0.31682 (17)   0.56580 (14)   0.60653 (9)    0.0156 (3)           
  C7     0.46580 (18)   0.61837 (14)   0.57545 (9)    0.0181 (3)           
  H7     0.450625       0.648514       0.521478       0.022\*              
  C8     0.53785 (19)   0.70697 (16)   0.63430 (10)   0.0223 (4)           
  H8     0.534938       0.790901       0.630565       0.027\*              
  C9     0.60537 (19)   0.64310 (16)   0.69172 (10)   0.0215 (4)           
  H9     0.663054       0.671359       0.737022       0.026\*              
  C10    0.57077 (18)   0.51491 (15)   0.66959 (9)    0.0173 (3)           
  C11    0.67413 (18)   0.41488 (15)   0.70014 (9)    0.0196 (4)           
  H11A   0.777907       0.426465       0.683886       0.023\*              
  H11B   0.683028       0.415179       0.756980       0.023\*              
  C12    0.45739 (18)   0.27365 (15)   0.69121 (9)    0.0187 (3)           
  H12A   0.456518       0.274715       0.747704       0.022\*              
  H12B   0.426248       0.193647       0.672394       0.022\*              
  C13    0.68211 (18)   0.24366 (16)   0.61696 (10)   0.0213 (4)           
  C14    0.61562 (19)   0.12361 (17)   0.58786 (11)   0.0268 (4)           
  C15    0.34324 (19)   0.52840 (15)   0.75488 (9)    0.0187 (4)           
  C16    0.4132 (2)     0.54441 (18)   0.88782 (9)    0.0294 (4)           
  H16A   0.502378       0.535376       0.926090       0.044\*              
  H16B   0.332265       0.489567       0.899623       0.044\*              
  H16C   0.375106       0.625921       0.888922       0.044\*              
  C17    0.20610 (18)   0.66654 (15)   0.61749 (9)    0.0171 (3)           
  C18    −0.0373 (2)    0.74427 (17)   0.57152 (12)   0.0332 (5)           
  H18A   −0.136339      0.716249       0.547019       0.050\*              
  H18B   −0.001422      0.810491       0.541928       0.050\*              
  H18C   −0.048909      0.770680       0.623910       0.050\*              
  N1     0.61226 (15)   0.30034 (12)   0.67137 (8)    0.0174 (3)           
  O1     0.35051 (12)   0.36756 (10)   0.57348 (6)    0.0157 (2)           
  O2     0.57083 (12)   0.52159 (10)   0.58756 (6)    0.0171 (3)           
  O3     0.79898 (15)   0.27623 (13)   0.59189 (8)    0.0386 (4)           
  O4     0.45760 (13)   0.51821 (11)   0.81186 (6)    0.0234 (3)           
  O5     0.21495 (14)   0.55547 (12)   0.76498 (7)    0.0274 (3)           
  O6     0.07292 (13)   0.64922 (10)   0.57403 (7)    0.0226 (3)           
  O7     0.23490 (14)   0.75410 (11)   0.65517 (7)    0.0263 (3)           
  F1     0.60895 (14)   0.04589 (10)   0.64497 (7)    0.0422 (3)           
  F2     0.47566 (12)   0.13074 (10)   0.55061 (6)    0.0350 (3)           
  F3     0.70476 (14)   0.07621 (12)   0.53923 (8)    0.0509 (4)           
  ------ -------------- -------------- -------------- -------------------- --

Atomic displacement parameters (Å^2^) {#d1e1146}
=====================================

  ----- ------------- ------------- ------------- ------------- ------------- -------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^       *U*^13^       *U*^23^
  C1    0.0169 (8)    0.0155 (8)    0.0130 (8)    −0.0009 (6)   0.0023 (6)    −0.0006 (6)
  C2    0.0181 (8)    0.0163 (8)    0.0139 (8)    −0.0018 (6)   0.0051 (6)    −0.0002 (6)
  C3    0.0172 (8)    0.0149 (8)    0.0254 (9)    −0.0042 (6)   0.0082 (7)    −0.0020 (7)
  C4    0.0163 (8)    0.0167 (9)    0.0244 (9)    −0.0025 (6)   0.0033 (6)    −0.0048 (7)
  C5    0.0173 (8)    0.0169 (8)    0.0153 (8)    0.0008 (6)    0.0002 (6)    −0.0011 (7)
  C6    0.0185 (8)    0.0150 (8)    0.0134 (8)    −0.0012 (6)   0.0022 (6)    −0.0005 (6)
  C7    0.0199 (8)    0.0168 (9)    0.0179 (8)    −0.0009 (6)   0.0039 (6)    0.0027 (7)
  C8    0.0226 (9)    0.0184 (9)    0.0268 (9)    −0.0068 (7)   0.0060 (7)    −0.0007 (7)
  C9    0.0213 (8)    0.0222 (9)    0.0205 (9)    −0.0071 (7)   −0.0002 (7)   −0.0038 (7)
  C10   0.0191 (8)    0.0184 (9)    0.0144 (8)    −0.0048 (6)   0.0024 (6)    −0.0019 (7)
  C11   0.0173 (8)    0.0230 (9)    0.0180 (8)    −0.0029 (7)   −0.0003 (6)   −0.0014 (7)
  C12   0.0181 (8)    0.0198 (9)    0.0193 (8)    −0.0011 (7)   0.0064 (6)    0.0027 (7)
  C13   0.0171 (8)    0.0241 (10)   0.0225 (9)    0.0007 (7)    0.0020 (7)    −0.0008 (7)
  C14   0.0226 (9)    0.0268 (10)   0.0315 (10)   0.0019 (7)    0.0048 (7)    −0.0048 (8)
  C15   0.0254 (9)    0.0149 (8)    0.0161 (8)    −0.0005 (7)   0.0042 (7)    0.0006 (7)
  C16   0.0470 (11)   0.0304 (11)   0.0114 (8)    0.0037 (9)    0.0057 (8)    −0.0025 (8)
  C17   0.0211 (8)    0.0172 (9)    0.0131 (8)    −0.0012 (6)   0.0030 (6)    0.0016 (7)
  C18   0.0299 (10)   0.0263 (11)   0.0409 (11)   0.0115 (8)    −0.0074 (8)   −0.0080 (9)
  N1    0.0158 (7)    0.0180 (7)    0.0184 (7)    −0.0010 (5)   0.0016 (5)    0.0014 (6)
  O1    0.0176 (5)    0.0157 (6)    0.0141 (6)    −0.0001 (4)   0.0034 (4)    −0.0016 (4)
  O2    0.0170 (6)    0.0201 (6)    0.0148 (6)    −0.0021 (5)   0.0039 (4)    0.0005 (5)
  O3    0.0259 (7)    0.0424 (9)    0.0509 (9)    −0.0105 (6)   0.0205 (6)    −0.0156 (7)
  O4    0.0297 (7)    0.0287 (7)    0.0116 (6)    0.0004 (5)    0.0019 (5)    −0.0020 (5)
  O5    0.0296 (7)    0.0322 (8)    0.0215 (6)    0.0095 (6)    0.0086 (5)    −0.0015 (5)
  O6    0.0212 (6)    0.0194 (6)    0.0261 (6)    0.0044 (5)    −0.0023 (5)   −0.0039 (5)
  O7    0.0296 (7)    0.0210 (7)    0.0272 (7)    0.0035 (5)    −0.0020 (5)   −0.0069 (5)
  F1    0.0515 (7)    0.0218 (6)    0.0523 (8)    0.0029 (5)    0.0002 (6)    0.0056 (5)
  F2    0.0279 (6)    0.0320 (6)    0.0427 (7)    −0.0024 (5)   −0.0073 (5)   −0.0102 (5)
  F3    0.0405 (7)    0.0496 (8)    0.0662 (9)    −0.0048 (6)   0.0225 (6)    −0.0341 (7)
  ----- ------------- ------------- ------------- ------------- ------------- -------------

Geometric parameters (Å, º) {#d1e1723}
===========================

  ---------------------- -------------- ---------------------- --------------
  C1---C15               1.512 (2)      C11---N1               1.471 (2)
  C1---C6                1.569 (2)      C11---H11A             0.9900
  C1---C10               1.579 (2)      C11---H11B             0.9900
  C1---C2                1.584 (2)      C12---N1               1.467 (2)
  C2---O1                1.4341 (19)    C12---H12A             0.9900
  C2---C12               1.507 (2)      C12---H12B             0.9900
  C2---C3                1.519 (2)      C13---O3               1.213 (2)
  C3---C4                1.326 (2)      C13---N1               1.347 (2)
  C3---H3                0.9500         C13---C14              1.541 (3)
  C4---C5                1.522 (2)      C14---F3               1.327 (2)
  C4---H4                0.9500         C14---F2               1.330 (2)
  C5---O1                1.4363 (19)    C14---F1               1.336 (2)
  C5---C6                1.572 (2)      C15---O5               1.196 (2)
  C5---H5                1.0000         C15---O4               1.343 (2)
  C6---C17               1.520 (2)      C16---O4               1.455 (2)
  C6---C7                1.582 (2)      C16---H16A             0.9800
  C7---O2                1.4303 (19)    C16---H16B             0.9800
  C7---C8                1.525 (2)      C16---H16C             0.9800
  C7---H7                1.0000         C17---O7               1.2006 (19)
  C8---C9                1.325 (2)      C17---O6               1.3393 (19)
  C8---H8                0.9500         C18---O6               1.441 (2)
  C9---C10               1.521 (2)      C18---H18A             0.9800
  C9---H9                0.9500         C18---H18B             0.9800
  C10---O2               1.4382 (19)    C18---H18C             0.9800
  C10---C11              1.510 (2)                             
                                                               
  C15---C1---C6          116.28 (13)    C9---C10---C1          106.00 (13)
  C15---C1---C10         115.76 (13)    N1---C11---C10         110.50 (12)
  C6---C1---C10          102.03 (12)    N1---C11---H11A        109.5
  C15---C1---C2          110.64 (13)    C10---C11---H11A       109.5
  C6---C1---C2           100.86 (12)    N1---C11---H11B        109.5
  C10---C1---C2          109.99 (12)    C10---C11---H11B       109.5
  O1---C2---C12          110.57 (12)    H11A---C11---H11B      108.1
  O1---C2---C3           101.16 (12)    N1---C12---C2          109.50 (13)
  C12---C2---C3          121.25 (13)    N1---C12---H12A        109.8
  O1---C2---C1           101.14 (11)    C2---C12---H12A        109.8
  C12---C2---C1          112.92 (13)    N1---C12---H12B        109.8
  C3---C2---C1           107.37 (13)    C2---C12---H12B        109.8
  C4---C3---C2           105.15 (14)    H12A---C12---H12B      108.2
  C4---C3---H3           127.4          O3---C13---N1          125.15 (16)
  C2---C3---H3           127.4          O3---C13---C14         116.83 (15)
  C3---C4---C5           106.05 (14)    N1---C13---C14         117.88 (14)
  C3---C4---H4           127.0          F3---C14---F2          106.54 (15)
  C5---C4---H4           127.0          F3---C14---F1          106.87 (16)
  O1---C5---C4           100.37 (12)    F2---C14---F1          107.23 (14)
  O1---C5---C6           101.94 (12)    F3---C14---C13         109.82 (14)
  C4---C5---C6           108.05 (13)    F2---C14---C13         113.97 (15)
  O1---C5---H5           114.9          F1---C14---C13         112.02 (15)
  C4---C5---H5           114.9          O5---C15---O4          123.51 (15)
  C6---C5---H5           114.9          O5---C15---C1          124.53 (15)
  C17---C6---C1          120.34 (13)    O4---C15---C1          111.90 (14)
  C17---C6---C5          112.90 (13)    O4---C16---H16A        109.5
  C1---C6---C5           100.09 (12)    O4---C16---H16B        109.5
  C17---C6---C7          108.88 (13)    H16A---C16---H16B      109.5
  C1---C6---C7           98.94 (12)     O4---C16---H16C        109.5
  C5---C6---C7           115.09 (13)    H16A---C16---H16C      109.5
  O2---C7---C8           100.74 (12)    H16B---C16---H16C      109.5
  O2---C7---C6           101.77 (12)    O7---C17---O6          123.57 (15)
  C8---C7---C6           108.18 (13)    O7---C17---C6          125.81 (15)
  O2---C7---H7           114.8          O6---C17---C6          110.43 (13)
  C8---C7---H7           114.8          O6---C18---H18A        109.5
  C6---C7---H7           114.8          O6---C18---H18B        109.5
  C9---C8---C7           106.02 (15)    H18A---C18---H18B      109.5
  C9---C8---H8           127.0          O6---C18---H18C        109.5
  C7---C8---H8           127.0          H18A---C18---H18C      109.5
  C8---C9---C10          105.27 (14)    H18B---C18---H18C      109.5
  C8---C9---H9           127.4          C13---N1---C12         124.77 (14)
  C10---C9---H9          127.4          C13---N1---C11         118.78 (13)
  O2---C10---C11         109.26 (13)    C12---N1---C11         114.62 (13)
  O2---C10---C9          100.58 (13)    C2---O1---C5           96.60 (11)
  C11---C10---C9         121.69 (14)    C7---O2---C10          96.93 (11)
  O2---C10---C1          101.56 (11)    C15---O4---C16         114.29 (13)
  C11---C10---C1         115.03 (13)    C17---O6---C18         116.74 (13)
                                                               
  C15---C1---C2---O1     158.98 (12)    C6---C1---C10---C9     73.08 (14)
  C6---C1---C2---O1      35.33 (13)     C2---C1---C10---C9     179.49 (12)
  C10---C1---C2---O1     −71.87 (14)    O2---C10---C11---N1    −65.07 (16)
  C15---C1---C2---C12    −82.85 (16)    C9---C10---C11---N1    178.56 (14)
  C6---C1---C2---C12     153.50 (12)    C1---C10---C11---N1    48.35 (17)
  C10---C1---C2---C12    46.30 (16)     O1---C2---C12---N1     57.13 (17)
  C15---C1---C2---C3     53.42 (16)     C3---C2---C12---N1     175.15 (14)
  C6---C1---C2---C3      −70.24 (14)    C1---C2---C12---N1     −55.37 (17)
  C10---C1---C2---C3     −177.43 (13)   O3---C13---C14---F3    0.8 (2)
  O1---C2---C3---C4      −32.33 (16)    N1---C13---C14---F3    −175.17 (15)
  C12---C2---C3---C4     −154.93 (15)   O3---C13---C14---F2    −118.68 (18)
  C1---C2---C3---C4      73.22 (16)     N1---C13---C14---F2    65.4 (2)
  C2---C3---C4---C5      −0.44 (17)     O3---C13---C14---F1    119.35 (18)
  C3---C4---C5---O1      32.93 (16)     N1---C13---C14---F1    −56.6 (2)
  C3---C4---C5---C6      −73.38 (16)    C6---C1---C15---O5     35.8 (2)
  C15---C1---C6---C17    4.8 (2)        C10---C1---C15---O5    155.57 (16)
  C10---C1---C6---C17    −122.10 (14)   C2---C1---C15---O5     −78.4 (2)
  C2---C1---C6---C17     124.52 (14)    C6---C1---C15---O4     −146.90 (14)
  C15---C1---C6---C5     −119.37 (14)   C10---C1---C15---O4    −27.14 (19)
  C10---C1---C6---C5     113.70 (12)    C2---C1---C15---O4     98.85 (15)
  C2---C1---C6---C5      0.31 (13)      C1---C6---C17---O7     58.2 (2)
  C15---C1---C6---C7     122.99 (14)    C5---C6---C17---O7     176.13 (15)
  C10---C1---C6---C7     −3.95 (14)     C7---C6---C17---O7     −54.7 (2)
  C2---C1---C6---C7      −117.33 (12)   C1---C6---C17---O6     −126.65 (15)
  O1---C5---C6---C17     −165.16 (12)   C5---C6---C17---O6     −8.77 (18)
  C4---C5---C6---C17     −59.95 (17)    C7---C6---C17---O6     120.36 (14)
  O1---C5---C6---C1      −35.94 (13)    O3---C13---N1---C12    167.96 (17)
  C4---C5---C6---C1      69.27 (14)     C14---C13---N1---C12   −16.5 (2)
  O1---C5---C6---C7      68.99 (15)     O3---C13---N1---C11    4.3 (3)
  C4---C5---C6---C7      174.20 (13)    C14---C13---N1---C11   179.81 (14)
  C17---C6---C7---O2     165.38 (12)    C2---C12---N1---C13    −101.78 (18)
  C1---C6---C7---O2      38.92 (14)     C2---C12---N1---C11    62.52 (17)
  C5---C6---C7---O2      −66.71 (16)    C10---C11---N1---C13   106.74 (16)
  C17---C6---C7---C8     59.79 (16)     C10---C11---N1---C12   −58.57 (17)
  C1---C6---C7---C8      −66.68 (15)    C12---C2---O1---C5     −178.88 (12)
  C5---C6---C7---C8      −172.31 (13)   C3---C2---O1---C5      51.41 (13)
  O2---C7---C8---C9      −31.04 (16)    C1---C2---O1---C5      −59.02 (12)
  C6---C7---C8---C9      75.27 (16)     C4---C5---O1---C2      −51.23 (13)
  C7---C8---C9---C10     −1.76 (17)     C6---C5---O1---C2      59.90 (13)
  C8---C9---C10---O2     33.85 (16)     C8---C7---O2---C10     50.57 (13)
  C8---C9---C10---C11    154.49 (15)    C6---C7---O2---C10     −60.77 (13)
  C8---C9---C10---C1     −71.55 (16)    C11---C10---O2---C7    179.05 (12)
  C15---C1---C10---O2    −158.88 (13)   C9---C10---O2---C7     −51.80 (13)
  C6---C1---C10---O2     −31.61 (14)    C1---C10---O2---C7     57.12 (13)
  C2---C1---C10---O2     74.81 (14)     O5---C15---O4---C16    −0.7 (2)
  C15---C1---C10---C11   83.27 (17)     C1---C15---O4---C16    −178.05 (14)
  C6---C1---C10---C11    −149.45 (13)   O7---C17---O6---C18    2.2 (2)
  C2---C1---C10---C11    −43.04 (17)    C6---C17---O6---C18    −173.02 (14)
  C15---C1---C10---C9    −54.19 (17)                           
  ---------------------- -------------- ---------------------- --------------

Hydrogen-bond geometry (Å, º) {#d1e2942}
=============================

  ------------------------ --------- --------- ------------- ---------------
  *D*---H···*A*            *D*---H   H···*A*   *D*···*A*     *D*---H···*A*
  C4---H4···O3^i^          0.95      2.44      3.116 (2)     128
  C5---H5···O2^ii^         1.00      2.60      3.1960 (19)   118
  C7---H7···O1^ii^         1.00      2.54      3.2091 (19)   124
  C11---H11*B*···O4        0.99      2.57      3.093 (2)     113
  C12---H12*A*···O7^iii^   0.99      2.52      3.328 (2)     138
  C12---H12*B*···O5^iii^   0.99      2.34      3.030 (2)     127
  C12---H12*B*···F1        0.99      2.40      3.043 (2)     122
  C12---H12*B*···F2        0.99      2.33      2.962 (2)     121
  C16---H16*A*···F3^iv^    0.98      2.62      3.475 (2)     146
  ------------------------ --------- --------- ------------- ---------------

Symmetry codes: (i) *x*−1, *y*, *z*; (ii) −*x*+1, −*y*+1, −*z*+1; (iii) −*x*+1/2, *y*−1/2, −*z*+3/2; (iv) −*x*+3/2, *y*+1/2, −*z*+3/2.

![The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.](e-74-01599-fig1){#fig1}

![The crystal structure of the title compound in a view along \[100\], emphasizing the inter­molecular C---H⋯O and C---H⋯F hydrogen bonds (dashed lines).](e-74-01599-fig2){#fig2}

![Hirshfeld surface of the title compound mapped over *d* ~norm~.](e-74-01599-fig3){#fig3}

![The two-dimensional fingerprint plots of the title compound, showing (*a*) all inter­actions, and delineated into (*b*) H⋯H, (*c*) O⋯H/ H⋯O, (*d*) F⋯H/H⋯F, (*e*) C⋯H/H⋯C, (*f*) F⋯F, (*g*) F⋯O/O⋯F, (*h*) O⋯O, (*i*) N⋯H/H⋯N and (*j*) C⋯O/O⋯C inter­actions \[*d* ~e~ and *d* ~i~ represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (inter­nal) the surface, respectively\].](e-74-01599-fig4){#fig4}

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*            *D*---H   H⋯*A*   *D*⋯*A*       *D*---H⋯*A*
  ---------------------- --------- ------- ------------- -------------
  C4---H4⋯O3^i^          0.95      2.44    3.116 (2)     128
  C5---H5⋯O2^ii^         1.00      2.60    3.1960 (19)   118
  C7---H7⋯O1^ii^         1.00      2.54    3.2091 (19)   124
  C11---H11*B*⋯O4        0.99      2.57    3.093 (2)     113
  C12---H12*A*⋯O7^iii^   0.99      2.52    3.328 (2)     138
  C12---H12*B*⋯O5^iii^   0.99      2.34    3.030 (2)     127
  C12---H12*B*⋯F1        0.99      2.40    3.043 (2)     122
  C12---H12*B*⋯F2        0.99      2.33    2.962 (2)     121
  C16---H16*A*⋯F3^iv^    0.98      2.62    3.475 (2)     146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

###### Percentage contributions of inter­atomic contacts to the Hirshfeld surface for the title compound

  Contact   Percentage contribution
  --------- -------------------------
  H⋯H       35.6
  O⋯H/H⋯O   28.5
  F⋯H/H⋯F   23.8
  C⋯H/H⋯C   5.5
  F⋯F       2.7
  F⋯O/O⋯F   1.6
  N⋯H/H⋯N   1.1
  O⋯O       1.1
  C⋯O/O⋯C   0.2

###### Experimental details

  -------------------------------------------------------------------------- -----------------------------------------------------
  Crystal data                                                               
  Chemical formula                                                           C~18~H~16~F~3~NO~7~
  *M* ~r~                                                                    415.32
  Crystal system, space group                                                Monoclinic, *P*2~1~/*n*
  Temperature (K)                                                            150
  *a*, *b*, *c* (Å)                                                          8.7661 (2), 11.2908 (3), 17.5089 (4)
  β (°)                                                                      96.021 (1)
  *V* (Å^3^)                                                                 1723.41 (7)
  *Z*                                                                        4
  Radiation type                                                             Mo *K*α
  μ (mm^−1^)                                                                 0.14
  Crystal size (mm)                                                          0.35 × 0.32 × 0.30
                                                                             
  Data collection                                                            
  Diffractometer                                                             Bruker APEXII CCD
  Absorption correction                                                      Multi-scan (*SADABS*; Krause *et al.*, 2015[@bb11])
  *T* ~min~, *T* ~max~                                                       0.942, 0.946
  No. of measured, independent and observed \[*I* \> 2σ(*I*)\] reflections   11170, 3496, 2739
  *R* ~int~                                                                  0.028
  (sin θ/λ)~max~ (Å^−1^)                                                     0.626
                                                                             
  Refinement                                                                 
  *R*\[*F* ^2^ \> 2σ(*F* ^2^)\], *wR*(*F* ^2^), *S*                          0.036, 0.091, 1.01
  No. of reflections                                                         3496
  No. of parameters                                                          264
  H-atom treatment                                                           H-atom parameters constrained
  Δρ~max~, Δρ~min~ (e Å^−3^)                                                 0.30, −0.25
  -------------------------------------------------------------------------- -----------------------------------------------------

Computer programs: *APEX2* and *SAINT* (Bruker, 2007[@bb5]), *SHELXS97* (Sheldrick, 2008[@bb19]), *SHELXL2014* (Sheldrick, 2015[@bb20]), *ORTEP-3 for Windows* (Farrugia, 2012[@bb7]) and *PLATON* (Spek, 2009[@bb22]).
