Related literature   {#sec1}
====================

For pharmaceutical applications of Tramadol and related analgesics, see: Scott & Perry (2000[@bb9]). For related structures, see: Tessler & Goldberg (2004[@bb15]); Arman *et al.* (2010[@bb1]); Hemamalini & Fun (2010[@bb3]); Siddaraju *et al.* (2011[@bb12]); Lin & Zhang (2013[@bb5]); Smith (2014[@bb13]); Jasinski *et al.* (2015[@bb4]); Sun *et al.* (2012[@bb14]).

Experimental   {#sec2}
==============

Crystal data   {#sec2.1}
--------------

C~16~H~26~NO~2~ ^+^·C~7~H~5~O~2~ ^−^*M* *~r~* = 385.49Triclinic,*a* = 9.013 (4) Å*b* = 9.767 (4) Å*c* = 12.726 (6) Åα = 75.008 (16)°β = 89.79 (2)°γ = 76.493 (16)°*V* = 1050.3 (8) Å^3^*Z* = 2Mo *K*α radiationμ = 0.08 mm^−1^*T* = 293 K0.55 × 0.51 × 0.3 mm

Data collection   {#sec2.2}
-----------------

Rigaku Saturn724+ diffractometerAbsorption correction: multi-scan (*NUMABS*; Rigaku 1999[@bb7]) *T* ~min~ = 0.955, *T* ~max~ = 0.97511931 measured reflections5660 independent reflections3504 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.029

Refinement   {#sec2.3}
------------

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.053*wR*(*F* ^2^) = 0.134*S* = 1.035660 reflections257 parametersH-atom parameters constrainedΔρ~max~ = 0.17 e Å^−3^Δρ~min~ = −0.21 e Å^−3^

 {#d5e579}

Data collection: *CrystalClear SM Expert* (Rigaku, 2011[@bb8]); cell refinement: *CrystalClear SM Expert*; data reduction: *CrystalClear SM Expert*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXL2014* (Sheldrick, 2015[@bb11]); molecular graphics: *OLEX2* (Dolomanov *et al.*, 2009[@bb2]) and *Mercury* (Macrae *et al.*, 2008[@bb6]); software used to prepare material for publication: *OLEX2*.

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

Crystal structure: contains datablock(s) I. DOI: [10.1107/S2056989015019362/sj5480sup1.cif](http://dx.doi.org/10.1107/S2056989015019362/sj5480sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S2056989015019362/sj5480Isup2.hkl](http://dx.doi.org/10.1107/S2056989015019362/sj5480Isup2.hkl)

###### 

Click here for additional data file.

Supporting information file. DOI: [10.1107/S2056989015019362/sj5480Isup3.cml](http://dx.doi.org/10.1107/S2056989015019362/sj5480Isup3.cml)

###### 

Click here for additional data file.

. DOI: [10.1107/S2056989015019362/sj5480fig1.tif](http://dx.doi.org/10.1107/S2056989015019362/sj5480fig1.tif)

A view of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level and an intra­molecular hydrogen bond is drawn as a dashed line.

###### 

Click here for additional data file.

a . DOI: [10.1107/S2056989015019362/sj5480fig2.tif](http://dx.doi.org/10.1107/S2056989015019362/sj5480fig2.tif)

A viewed along the *a* axis of the crystal packing of the title compound. Hydrogen bonds are drawn as a dashed lines.

CCDC reference: [1425991](http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1425991)

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?sj5480&file=sj5480sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?sj5480sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?sj5480&checkcif=yes)

Supporting information for this paper is available from the IUCr electronic archives (Reference: [SJ5480](http://scripts.iucr.org/cgi-bin/sendsup?sj5480)).

The authors thank DST--PURSE, Mangalore University, Mangaluru, for providing the single-crystal X-ray diffraction facility. PN thanks Bharthi College, Maddur, for research facilities.

S1. Comment {#comment}
===========

2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol hydrochloride (Tramadol) is used in the treatment of disorders of the central nervous system and in treating extreme pain. This molecule is analogous to the phenanthrene alkaloid codeine and is used in the control of pre-operative pain (Scott & Perry, 2000).

There are number of crystal structures reported available related to this salt. These include Venlafaxine \[(*RS*)-1-\[2-dimethylamino-1-(4-methoxyphenyl)-ethyl\]- cyclohexanol\] (Tessler & Goldberg, 2004), benzoic acid-2-{(*E*)-\[(*E*)-2-(2-pyridylmethylidene) hydrazin-1-ylidene\]methyl}pyridine (2/1) (Arman *et al.*, 2010), 2,3-diaminopyridinium benzoate benzoic acid solvate (Hemamalini & Fun, 2010), Tramadol hydrochloride-benzoic acid (1/1) (Siddaraju *et al.*, 2011), 4-(*cyclo*-propane-carboxamido) benzoic acid (Sun *et al.*, 2012), 3,5-bis\[(pyridin-4-yl)meth-oxy\]benzoic acid (Lin & Zhang, 2013). The hydrogen-bonded two- and three-dimensional polymeric structures of the ammonium salts of 3,5-di-nitro-benzoic acid, 4-nitro-benzoic acid and 2,4-di-chloro-benzoic acid (Smith, 2014) and 4-\[1-(2-hydroxypropyl)-4,5-diphenyl-1*H*-imidazol-2-yl\]benzoic acid (Jasinski *et al.*, 2015) have also been reported. In the view of the importance of Tramadol, we report herein the crystal structure of the title compound 2-hydroxy-2-(3-methoxy-phenyl)-cyclohexylmethyl-dimethyl-ammonium benzoate.

In the title molecule (Fig. 1), the six membered cyclohexane ring (C9/C11--C15) adopts a slightly distorted chair conformation with ring puckering parameters Q, θ and φ of 0.5605 (16) Å, 5.06 (16)°, and 210.3 (6)°, respectively. An intramolecular C6---H6···O10 hydrogen bond (Fig 1, Table 1) is found in the cation. Bond lengths are within normal ranges.

The crystal structure is stabilized with weak intermolecular O---H···O, N---H···O and C---H···O hydrogen bonds and a weak intermolecular C23---H23···*Cg1* interaction is also observed Table 1, Fig. 2.

S2. Experimental {#experimental}
================

Tramadol (3 g, 0.01 mol) and benzoic acid (1 g, 0.01 mol) were each dissolved in 10 ml of ethanol. The solutions were mixed and stirred in a beaker at 333 K for 30 minutes. The mixture was kept aside for three days at room temperature. Colourless X-ray quality crystals were formed and one was used for the data collection

S3. Refinement {#refinement}
==============

Crystal data, data collection and structure refinement details are summarized in Table 1. The hydrogen atoms were fixed geometrically (C---H = 0.93--0.96 Å, N---H = 0.98 Å) and allowed to ride on their parent atoms with *U*~iso~(H) = 1.2*U*~eq~(C/N).

Figures
=======

![A view of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level and an intramolecular hydrogen bond is drawn as a dashed line.](e-71-0o864-fig1){#Fap1}

![A viewed along the a axis of the crystal packing of the title compound. Hydrogen bonds are drawn as a dashed lines.](e-71-0o864-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------------------ ---------------------------------------
  C~16~H~26~NO~2~^+^·C~7~H~5~O~2~^−^   *Z* = 2
  *M~r~* = 385.49                      *F*(000) = 416
  Triclinic, *P*1                      *D*~x~ = 1.219 Mg m^−3^
  *a* = 9.013 (4) Å                    Mo *K*α radiation, λ = 0.71075 Å
  *b* = 9.767 (4) Å                    Cell parameters from 5660 reflections
  *c* = 12.726 (6) Å                   θ = 3.0--29.5°
  α = 75.008 (16)°                     µ = 0.08 mm^−1^
  β = 89.79 (2)°                       *T* = 293 K
  γ = 76.493 (16)°                     Block, colourless
  *V* = 1050.3 (8) Å^3^                0.55 × 0.51 × 0.3 mm
  ------------------------------------ ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ----------------------------------------------------------- --------------------------------------
  Rigaku Saturn724+ diffractometer                            5660 independent reflections
  Radiation source: Sealed tube, Rotating Anode               3504 reflections with *I* \> 2σ(*I*)
  Confocal monochromator                                      *R*~int~ = 0.029
  Detector resolution: 28.5714 pixels mm^-1^                  θ~max~ = 29.5°, θ~min~ = 3.0°
  profile data from ω--scans                                  *h* = −12→11
  Absorption correction: multi-scan (*NUMABS*; Rigaku 1999)   *k* = −13→13
  *T*~min~ = 0.955, *T*~max~ = 0.975                          *l* = −17→14
  11931 measured reflections                                  
  ----------------------------------------------------------- --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Hydrogen site location: inferred from neighbouring sites
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.053   H-atom parameters constrained
  *wR*(*F*^2^) = 0.134                  *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0598*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.03                            (Δ/σ)~max~ = 0.001
  5660 reflections                      Δρ~max~ = 0.17 e Å^−3^
  257 parameters                        Δρ~min~ = −0.21 e Å^−3^
  0 restraints                          
  ------------------------------------- -------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

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

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

  ------ -------------- -------------- -------------- -------------------- --
         *x*            *y*            *z*            *U*~iso~\*/*U*~eq~   
  C1     0.51600 (17)   0.30154 (17)   0.58415 (12)   0.0418 (4)           
  C2     0.39216 (17)   0.38352 (18)   0.62190 (13)   0.0502 (4)           
  H2     0.2941         0.3959         0.5925         0.060\*              
  C3     0.41457 (17)   0.44717 (17)   0.70353 (14)   0.0520 (4)           
  H3     0.3314         0.5032         0.7290         0.062\*              
  C4     0.56018 (16)   0.42788 (16)   0.74757 (13)   0.0448 (4)           
  H4     0.5738         0.4708         0.8029         0.054\*              
  C5     0.68653 (15)   0.34553 (14)   0.71072 (11)   0.0332 (3)           
  C6     0.66294 (15)   0.28320 (15)   0.62715 (11)   0.0366 (3)           
  H6     0.7459         0.2291         0.6001         0.044\*              
  C8     0.6071 (2)     0.1648 (2)     0.45646 (15)   0.0697 (5)           
  H8A    0.5688         0.1311         0.4000         0.104\*              
  H8B    0.6659         0.0829         0.5111         0.104\*              
  H8C    0.6707         0.2297         0.4258         0.104\*              
  C9     0.84766 (14)   0.31719 (13)   0.76345 (10)   0.0310 (3)           
  C11    0.85527 (17)   0.21038 (15)   0.87622 (11)   0.0406 (3)           
  H11A   0.7688         0.2473         0.9152         0.049\*              
  H11B   0.8451         0.1174         0.8670         0.049\*              
  C12    1.00060 (18)   0.18474 (16)   0.94543 (12)   0.0465 (4)           
  H12A   1.0865         0.1338         0.9130         0.056\*              
  H12B   0.9923         0.1239         1.0176         0.056\*              
  C13    1.0282 (2)     0.32939 (16)   0.95426 (12)   0.0491 (4)           
  H13A   0.9471         0.3760         0.9929         0.059\*              
  H13B   1.1243         0.3118         0.9954         0.059\*              
  C14    1.03296 (17)   0.42967 (16)   0.84145 (11)   0.0417 (4)           
  H14A   1.1171         0.3845         0.8044         0.050\*              
  H14B   1.0512         0.5210         0.8486         0.050\*              
  C15    0.88435 (15)   0.46093 (13)   0.77334 (10)   0.0317 (3)           
  H15    0.8016         0.5100         0.8107         0.038\*              
  C16    0.88662 (16)   0.56049 (14)   0.65994 (10)   0.0358 (3)           
  H16A   0.9709         0.5144         0.6235         0.043\*              
  H16B   0.7929         0.5688         0.6190         0.043\*              
  C18    0.77644 (17)   0.79335 (16)   0.70698 (14)   0.0508 (4)           
  H18A   0.6805         0.8004         0.6709         0.076\*              
  H18B   0.7905         0.8896         0.7005         0.076\*              
  H18C   0.7767         0.7434         0.7826         0.076\*              
  C19    0.9145 (2)     0.79324 (17)   0.54203 (12)   0.0572 (5)           
  H19A   0.9985         0.7395         0.5112         0.086\*              
  H19B   0.9315         0.8870         0.5410         0.086\*              
  H19C   0.8215         0.8062         0.5001         0.086\*              
  N17    0.90203 (13)   0.71131 (11)   0.65610 (9)    0.0337 (3)           
  H17    0.9976         0.7013         0.6970         0.040\*              
  O7     0.48324 (13)   0.23977 (15)   0.50425 (10)   0.0642 (3)           
  O10    0.96103 (10)   0.26098 (10)   0.69699 (8)    0.0372 (2)           
  H10    0.9774         0.1717         0.7133         0.056\*              
  C20    0.38473 (18)   0.75688 (18)   0.88067 (13)   0.0492 (4)           
  H20    0.3598         0.6668         0.8964         0.059\*              
  C21    0.29160 (16)   0.87614 (15)   0.80738 (11)   0.0376 (3)           
  C22    0.33245 (18)   1.00897 (17)   0.78461 (12)   0.0471 (4)           
  H22    0.2706         1.0903         0.7362         0.056\*              
  C23    0.4632 (2)     1.0218 (2)     0.83276 (14)   0.0564 (4)           
  H23    0.4902         1.1110         0.8155         0.068\*              
  C24    0.5540 (2)     0.9031 (2)     0.90636 (14)   0.0595 (5)           
  H24    0.6417         0.9121         0.9396         0.071\*              
  C25    0.51482 (19)   0.7706 (2)     0.93080 (13)   0.0597 (5)           
  H25    0.5757         0.6903         0.9809         0.072\*              
  C26    0.15086 (16)   0.86086 (15)   0.75316 (12)   0.0385 (3)           
  O27    0.05139 (13)   0.97122 (11)   0.70637 (10)   0.0600 (3)           
  O28    0.14406 (12)   0.73144 (11)   0.75774 (9)    0.0529 (3)           
  ------ -------------- -------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- ------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^       *U*^23^
  C1    0.0387 (8)    0.0477 (9)    0.0414 (8)    −0.0137 (7)    0.0007 (7)    −0.0132 (7)
  C2    0.0321 (8)    0.0561 (10)   0.0601 (10)   −0.0087 (7)    −0.0010 (7)   −0.0132 (8)
  C3    0.0344 (8)    0.0496 (9)    0.0740 (12)   −0.0053 (7)    0.0125 (8)    −0.0245 (8)
  C4    0.0378 (8)    0.0443 (9)    0.0602 (10)   −0.0115 (7)    0.0102 (7)    −0.0262 (7)
  C5    0.0323 (7)    0.0281 (7)    0.0405 (8)    −0.0102 (5)    0.0069 (6)    −0.0088 (6)
  C6    0.0330 (7)    0.0382 (7)    0.0400 (8)    −0.0092 (6)    0.0056 (6)    −0.0123 (6)
  C8    0.0581 (11)   0.0930 (15)   0.0678 (12)   −0.0084 (10)   −0.0036 (9)   −0.0474 (11)
  C9    0.0315 (7)    0.0276 (6)    0.0357 (7)    −0.0079 (5)    0.0060 (6)    −0.0110 (5)
  C11   0.0485 (9)    0.0320 (7)    0.0422 (8)    −0.0154 (6)    0.0049 (7)    −0.0066 (6)
  C12   0.0566 (10)   0.0363 (8)    0.0421 (8)    −0.0103 (7)    −0.0034 (7)   −0.0031 (6)
  C13   0.0608 (10)   0.0446 (9)    0.0418 (8)    −0.0145 (8)    −0.0104 (8)   −0.0094 (7)
  C14   0.0459 (8)    0.0378 (8)    0.0459 (8)    −0.0181 (7)    −0.0024 (7)   −0.0117 (6)
  C15   0.0373 (7)    0.0265 (6)    0.0340 (7)    −0.0107 (5)    0.0048 (6)    −0.0103 (5)
  C16   0.0453 (8)    0.0308 (7)    0.0353 (7)    −0.0145 (6)    0.0059 (6)    −0.0109 (6)
  C18   0.0457 (9)    0.0358 (8)    0.0688 (11)   −0.0039 (7)    0.0084 (8)    −0.0157 (8)
  C19   0.0827 (13)   0.0446 (9)    0.0448 (9)    −0.0267 (9)    0.0087 (9)    −0.0026 (7)
  N17   0.0359 (6)    0.0283 (6)    0.0367 (6)    −0.0095 (5)    0.0029 (5)    −0.0068 (5)
  O7    0.0439 (7)    0.0989 (10)   0.0628 (7)    −0.0173 (6)    −0.0012 (6)   −0.0441 (7)
  O10   0.0351 (5)    0.0303 (5)    0.0485 (6)    −0.0063 (4)    0.0100 (4)    −0.0159 (4)
  C20   0.0484 (9)    0.0480 (9)    0.0520 (9)    −0.0139 (7)    0.0082 (8)    −0.0130 (7)
  C21   0.0389 (8)    0.0382 (8)    0.0414 (8)    −0.0117 (6)    0.0102 (7)    −0.0181 (6)
  C22   0.0516 (9)    0.0422 (9)    0.0537 (9)    −0.0166 (7)    0.0031 (8)    −0.0189 (7)
  C23   0.0552 (10)   0.0590 (11)   0.0692 (11)   −0.0273 (9)    0.0082 (9)    −0.0298 (9)
  C24   0.0468 (10)   0.0835 (14)   0.0627 (11)   −0.0240 (10)   0.0060 (9)    −0.0373 (10)
  C25   0.0486 (10)   0.0716 (12)   0.0551 (10)   −0.0090 (9)    −0.0020 (8)   −0.0146 (9)
  C26   0.0404 (8)    0.0322 (7)    0.0480 (9)    −0.0109 (6)    0.0092 (7)    −0.0180 (6)
  O27   0.0577 (7)    0.0345 (6)    0.0870 (8)    −0.0044 (5)    −0.0161 (7)   −0.0205 (6)
  O28   0.0441 (6)    0.0321 (5)    0.0852 (8)    −0.0119 (5)    −0.0046 (6)   −0.0178 (5)
  ----- ------------- ------------- ------------- -------------- ------------- --------------

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

  ----------------------- -------------- ----------------------- --------------
  C1---C2                 1.377 (2)      C14---C15               1.5229 (19)
  C1---C6                 1.389 (2)      C15---H15               0.9800
  C1---O7                 1.3739 (19)    C15---C16               1.5204 (18)
  C2---H2                 0.9300         C16---H16A              0.9700
  C2---C3                 1.379 (2)      C16---H16B              0.9700
  C3---H3                 0.9300         C16---N17               1.5000 (17)
  C3---C4                 1.381 (2)      C18---H18A              0.9600
  C4---H4                 0.9300         C18---H18B              0.9600
  C4---C5                 1.3881 (18)    C18---H18C              0.9600
  C5---C6                 1.3944 (19)    C18---N17               1.4771 (17)
  C5---C9                 1.5359 (19)    C19---H19A              0.9600
  C6---H6                 0.9300         C19---H19B              0.9600
  C8---H8A                0.9600         C19---H19C              0.9600
  C8---H8B                0.9600         C19---N17               1.4833 (18)
  C8---H8C                0.9600         N17---H17               0.9800
  C8---O7                 1.4126 (19)    O10---H10               0.8200
  C9---C11                1.5314 (19)    C20---H20               0.9300
  C9---C15                1.5507 (18)    C20---C21               1.385 (2)
  C9---O10                1.4257 (15)    C20---C25               1.386 (2)
  C11---H11A              0.9700         C21---C22               1.389 (2)
  C11---H11B              0.9700         C21---C26               1.502 (2)
  C11---C12               1.515 (2)      C22---H22               0.9300
  C12---H12A              0.9700         C22---C23               1.376 (2)
  C12---H12B              0.9700         C23---H23               0.9300
  C12---C13               1.522 (2)      C23---C24               1.376 (2)
  C13---H13A              0.9700         C24---H24               0.9300
  C13---H13B              0.9700         C24---C25               1.379 (2)
  C13---C14               1.521 (2)      C25---H25               0.9300
  C14---H14A              0.9700         C26---O27               1.2412 (17)
  C14---H14B              0.9700         C26---O28               1.2661 (17)
                                                                 
  C2---C1---C6            120.59 (14)    C9---C15---H15          107.9
  O7---C1---C2            115.75 (14)    C14---C15---C9          110.98 (11)
  O7---C1---C6            123.65 (14)    C14---C15---H15         107.9
  C1---C2---H2            120.2          C16---C15---C9          109.26 (10)
  C1---C2---C3            119.53 (14)    C16---C15---C14         112.67 (11)
  C3---C2---H2            120.2          C16---C15---H15         107.9
  C2---C3---H3            119.9          C15---C16---H16A        108.4
  C2---C3---C4            120.17 (15)    C15---C16---H16B        108.4
  C4---C3---H3            119.9          H16A---C16---H16B       107.5
  C3---C4---H4            119.4          N17---C16---C15         115.49 (10)
  C3---C4---C5            121.20 (14)    N17---C16---H16A        108.4
  C5---C4---H4            119.4          N17---C16---H16B        108.4
  C4---C5---C6            118.22 (13)    H18A---C18---H18B       109.5
  C4---C5---C9            121.36 (12)    H18A---C18---H18C       109.5
  C6---C5---C9            120.36 (12)    H18B---C18---H18C       109.5
  C1---C6---C5            120.28 (13)    N17---C18---H18A        109.5
  C1---C6---H6            119.9          N17---C18---H18B        109.5
  C5---C6---H6            119.9          N17---C18---H18C        109.5
  H8A---C8---H8B          109.5          H19A---C19---H19B       109.5
  H8A---C8---H8C          109.5          H19A---C19---H19C       109.5
  H8B---C8---H8C          109.5          H19B---C19---H19C       109.5
  O7---C8---H8A           109.5          N17---C19---H19A        109.5
  O7---C8---H8B           109.5          N17---C19---H19B        109.5
  O7---C8---H8C           109.5          N17---C19---H19C        109.5
  C5---C9---C15           111.34 (10)    C16---N17---H17         107.6
  C11---C9---C5           107.75 (10)    C18---N17---C16         112.99 (11)
  C11---C9---C15          110.47 (11)    C18---N17---C19         110.77 (12)
  O10---C9---C5           110.85 (11)    C18---N17---H17         107.6
  O10---C9---C11          111.47 (11)    C19---N17---C16         110.13 (10)
  O10---C9---C15          105.01 (10)    C19---N17---H17         107.6
  C9---C11---H11A         108.6          C1---O7---C8            117.87 (12)
  C9---C11---H11B         108.6          C9---O10---H10          109.5
  H11A---C11---H11B       107.6          C21---C20---H20         119.7
  C12---C11---C9          114.67 (12)    C21---C20---C25         120.58 (16)
  C12---C11---H11A        108.6          C25---C20---H20         119.7
  C12---C11---H11B        108.6          C20---C21---C22         118.47 (14)
  C11---C12---H12A        109.6          C20---C21---C26         120.42 (13)
  C11---C12---H12B        109.6          C22---C21---C26         121.10 (13)
  C11---C12---C13         110.42 (12)    C21---C22---H22         119.5
  H12A---C12---H12B       108.1          C23---C22---C21         120.94 (15)
  C13---C12---H12A        109.6          C23---C22---H22         119.5
  C13---C12---H12B        109.6          C22---C23---H23         119.9
  C12---C13---H13A        109.6          C24---C23---C22         120.10 (16)
  C12---C13---H13B        109.6          C24---C23---H23         119.9
  H13A---C13---H13B       108.1          C23---C24---H24         120.1
  C14---C13---C12         110.39 (12)    C23---C24---C25         119.87 (16)
  C14---C13---H13A        109.6          C25---C24---H24         120.1
  C14---C13---H13B        109.6          C20---C25---H25         120.0
  C13---C14---H14A        109.3          C24---C25---C20         120.03 (16)
  C13---C14---H14B        109.3          C24---C25---H25         120.0
  C13---C14---C15         111.70 (12)    O27---C26---C21         120.10 (13)
  H14A---C14---H14B       107.9          O27---C26---O28         124.15 (14)
  C15---C14---H14A        109.3          O28---C26---C21         115.75 (13)
  C15---C14---H14B        109.3                                  
                                                                 
  C1---C2---C3---C4       −0.4 (2)       C12---C13---C14---C15   59.28 (17)
  C2---C1---C6---C5       1.2 (2)        C13---C14---C15---C9    −56.84 (15)
  C2---C1---O7---C8       174.83 (15)    C13---C14---C15---C16   −179.74 (12)
  C2---C3---C4---C5       0.4 (2)        C14---C15---C16---N17   −63.19 (16)
  C3---C4---C5---C6       0.4 (2)        C15---C9---C11---C12    −51.00 (15)
  C3---C4---C5---C9       −176.79 (13)   C15---C16---N17---C18   −59.79 (16)
  C4---C5---C6---C1       −1.23 (19)     C15---C16---N17---C19   175.76 (12)
  C4---C5---C9---C11      71.47 (15)     O7---C1---C2---C3       178.80 (14)
  C4---C5---C9---C15      −49.81 (16)    O7---C1---C6---C5       −177.88 (13)
  C4---C5---C9---O10      −166.32 (11)   O10---C9---C11---C12    65.34 (15)
  C5---C9---C11---C12     −172.82 (11)   O10---C9---C15---C14    −68.97 (13)
  C5---C9---C15---C14     171.00 (10)    O10---C9---C15---C16    55.87 (13)
  C5---C9---C15---C16     −64.15 (13)    C20---C21---C22---C23   0.7 (2)
  C6---C1---C2---C3       −0.3 (2)       C20---C21---C26---O27   164.70 (14)
  C6---C1---O7---C8       −6.0 (2)       C20---C21---C26---O28   −16.30 (19)
  C6---C5---C9---C11      −105.71 (14)   C21---C20---C25---C24   −1.2 (2)
  C6---C5---C9---C15      133.01 (13)    C21---C22---C23---C24   −1.4 (2)
  C6---C5---C9---O10      16.51 (16)     C22---C21---C26---O27   −16.0 (2)
  C9---C5---C6---C1       176.03 (12)    C22---C21---C26---O28   163.00 (13)
  C9---C11---C12---C13    53.62 (16)     C22---C23---C24---C25   0.8 (2)
  C9---C15---C16---N17    172.96 (11)    C23---C24---C25---C20   0.5 (2)
  C11---C9---C15---C14    51.32 (14)     C25---C20---C21---C22   0.6 (2)
  C11---C9---C15---C16    176.17 (11)    C25---C20---C21---C26   179.94 (13)
  C11---C12---C13---C14   −56.17 (17)    C26---C21---C22---C23   −178.64 (13)
  ----------------------- -------------- ----------------------- --------------

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

Cg1 is the centroid of the C1--C6 benzene ring.

  ------------------------ --------- --------- ------------- ---------------
  *D*---H···*A*            *D*---H   H···*A*   *D*···*A*     *D*---H···*A*
  C6---H6···O10            0.93      2.42      2.775 (2)     102
  C14---H14*B*···O28^i^    0.97      2.41      3.251 (2)     144
  N17---H17···O28^i^       0.98      1.65      2.6120 (18)   165
  O10---H10···O27^ii^      0.82      1.94      2.7269 (17)   161
  C23---H23···*Cg*1^iii^   0.93      2.83      3.684 (3)     153
  ------------------------ --------- --------- ------------- ---------------

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

###### Hydrogen-bond geometry (, )

*Cg*1 is the centroid of the C1C6 benzene ring.

  *D*H*A*            *D*H   H*A*   *D* *A*      *D*H*A*
  ------------------ ------ ------ ------------ ---------
  C6H6O10            0.93   2.42   2.775(2)     102
  C14H14*B*O28^i^    0.97   2.41   3.251(2)     144
  N17H17O28^i^       0.98   1.65   2.6120(18)   165
  O10H10O27^ii^      0.82   1.94   2.7269(17)   161
  C23H23*Cg*1^iii^   0.93   2.83   3.684(3)     153

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