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

For general background to the use of Schiff base derivatives in the development of protein and enzyme mimics, see: Santos *et al.* (2001[@bb5]). For related structures, see: Zhang *et al.* (2006[@bb8]); Han *et al.* (2008[@bb4]); Guo *et al.* (2010[@bb3]). For reference bond-length data, see: Allen *et al.* (1987[@bb1]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~25~H~22~ClN~3~O~5~S*M* *~r~* = 511.98Monoclinic,*a* = 11.063 (2) Å*b* = 10.153 (2) Å*c* = 22.159 (4) Åβ = 98.73 (3)°*V* = 2460.1 (8) Å^3^*Z* = 4Mo *K*α radiationμ = 0.28 mm^−1^*T* = 294 K0.30 × 0.26 × 0.18 mm

### Data collection   {#sec2.1.2}

Bruker SMART APEX CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Sheldrick, 1996[@bb6]) *T* ~min~ = 0.907, *T* ~max~ = 0.95119683 measured reflections4315 independent reflections3016 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.052

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.056*wR*(*F* ^2^) = 0.154*S* = 1.004315 reflections319 parametersH-atom parameters constrainedΔρ~max~ = 0.34 e Å^−3^Δρ~min~ = −0.45 e Å^−3^

 {#d5e400}

Data collection: *SMART* (Bruker, 1999[@bb2]); cell refinement: *SAINT* (Bruker, 1999[@bb2]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb7]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb7]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb7]); software used to prepare material for publication: *SHELXTL*.

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

Crystal structure: contains datablock(s) I, global. DOI: [10.1107/S160053681202627X/cv5310sup1.cif](http://dx.doi.org/10.1107/S160053681202627X/cv5310sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S160053681202627X/cv5310Isup2.hkl](http://dx.doi.org/10.1107/S160053681202627X/cv5310Isup2.hkl)

Supplementary material file. DOI: [10.1107/S160053681202627X/cv5310Isup3.cml](http://dx.doi.org/10.1107/S160053681202627X/cv5310Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?cv5310&file=cv5310sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?cv5310sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?cv5310&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [CV5310](http://scripts.iucr.org/cgi-bin/sendsup?cv5310)).

Comment
=======

Schiff bases have extensively been studied because of their potentially biological activities such as protein and enzyme mimics (Santos *et al.*, 2001). Among the large number of compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them, such as (*E*)-5-((1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1*H*-pyrazol-4-ylimino)methyl) -2-methoxyphenyl 4-bromobenzenesulfonate (Guo *et al.*, 2010), (*E*)-4-((1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1*H*-pyrazol-4-ylimino)methyl) phenyl 4-bromobenzenesulfonate (Han *et al.*, 2008) and (*E*)-4-(2-(4-Chlorobenzyloxy)benzylideneamino) -2,3-dimethyl-1-phenyl-1,2-dihydropyrazol-5-one (Zhang *et al.*, 2006) have been reported. Herewith we report the synthesis and crystal structure of the title Schiff base compound.

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen *et al.*, 1987). Two N atoms in the pyrazole ring have a pyramidal environment with the sums of the valence angles around them of 349.3 (2) and 357.5 (2)°, respectively. The phenyl ring is twisted at 50.97 (12)° from the pyrazole mean plane. The central benzene ring (C7---C12) with three attached atoms (C14/O3/O4) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0392 Å. The mean plane of this fragment formss dihedral angles of 32.89 (8)°, 38.18 (10)° and 82.42 (7)°, respectively, with the the pyrazolone ring (C15---C17/N1---N3/O5), the chlorobenzene ring (C1---C6) and the terminal phenyl ring (C20---C25). Similar values of 32.02 (14)°, 37.49 (18)° and 80.52 (13)°, respectively, were observed in isostructural (*E*)-5-((1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1*H*-pyrazol -4-ylimino)methyl)-2-methoxyphenyl 4-bromobenzenesulfonate (Guo *et al.*, 2010).

In the crystal, non-classical intermolecular C11---H11···O5═ C16 hydrogen bonds (Table 1) form inversion-related dimers (Fig. 2).

Experimental {#experimental}
============

An anhydrous ethanol solution (100 ml) of 5-formyl-2-methoxyphenyl 4-chlorobenzenesulfonate (3.27 g, 10 mmol) was added to an anhydrous ethanol solution (100 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) and the mixture refluxed for 3 h under N~2~, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile, and then dried in a vacuum to give pure compound (I) in 76% yield. Yellow single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

Refinement {#refinement}
==========

The H atoms were included in calculated positions and refined using a riding model approximation. Constrained C---H bond lengths and isotropic U parameters: 0.93 Å and *U*~iso~(H) = 1.2*U*~eq~(C) for C*sp*^2^---H; 0.96 Å and *U*~iso~(H) = 1.5*U*~eq~(C) for methyl C---H.

Figures
=======

![The structure of the title molecule, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.](e-68-o2110-fig1){#Fap1}

![A portion of the crystal packing showing weak C---H···O interactions as dashed lines.](e-68-o2110-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~25~H~22~ClN~3~O~5~S     *F*(000) = 1064
  *M~r~* = 511.98           *D*~x~ = 1.382 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 5316 reflections
  *a* = 11.063 (2) Å        θ = 2.7--27.9°
  *b* = 10.153 (2) Å        µ = 0.28 mm^−1^
  *c* = 22.159 (4) Å        *T* = 294 K
  β = 98.73 (3)°            Block, yellow
  *V* = 2460.1 (8) Å^3^     0.30 × 0.26 × 0.18 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

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

  --------------------------------------------------------------- --------------------------------------
  Bruker SMART APEX CCD area-detector diffractometer              4315 independent reflections
  Radiation source: fine-focus sealed tube                        3016 reflections with *I* \> 2σ(*I*)
  Graphite monochromator                                          *R*~int~ = 0.052
  φ and ω scans                                                   θ~max~ = 25.0°, θ~min~ = 2.4°
  Absorption correction: multi-scan (*SADABS*; Sheldrick, 1996)   *h* = −11→13
  *T*~min~ = 0.907, *T*~max~ = 0.951                              *k* = −12→11
  19683 measured reflections                                      *l* = −26→26
  --------------------------------------------------------------- --------------------------------------

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

  ------------------------------------- -------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.056   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.154                  H-atom parameters constrained
  *S* = 1.00                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0919*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4315 reflections                      (Δ/σ)~max~ \< 0.001
  319 parameters                        Δρ~max~ = 0.34 e Å^−3^
  0 restraints                          Δρ~min~ = −0.45 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------

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.
  Refinement. Refinement of *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> 2σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ are statistically about twice as large as those based on *F*, and *R*- factors based on ALL data will be even larger.
  ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

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

  ------ -------------- --------------- --------------- -------------------- --
         *x*            *y*             *z*             *U*~iso~\*/*U*~eq~   
  Cl1    0.47353 (11)   1.05947 (9)     0.12284 (7)     0.1381 (5)           
  S1     0.44039 (6)    0.44761 (7)     0.13133 (3)     0.0563 (3)           
  N1     0.80799 (17)   0.1811 (2)      0.00538 (9)     0.0454 (5)           
  N2     0.91575 (19)   0.0090 (2)      −0.11867 (10)   0.0515 (6)           
  N3     0.88868 (18)   −0.09430 (19)   −0.08078 (9)    0.0477 (5)           
  O1     0.36954 (18)   0.4061 (2)      0.17629 (10)    0.0786 (7)           
  O2     0.41778 (17)   0.3950 (2)      0.07100 (9)     0.0729 (6)           
  O3     0.57713 (14)   0.40946 (15)    0.16147 (7)     0.0497 (5)           
  O4     0.70559 (15)   0.62701 (17)    0.19204 (8)     0.0548 (5)           
  O5     0.92591 (17)   0.23713 (16)    −0.11241 (9)    0.0617 (5)           
  C1     0.4426 (2)     0.6207 (3)      0.12761 (12)    0.0516 (7)           
  C2     0.4230 (3)     0.6931 (3)      0.17786 (15)    0.0699 (8)           
  H2     0.4046         0.6510          0.2126          0.084\*              
  C3     0.4310 (3)     0.8292 (3)      0.17608 (19)    0.0835 (10)          
  H3     0.4171         0.8797          0.2094          0.100\*              
  C4     0.4600 (3)     0.8884 (3)      0.1241 (2)      0.0829 (10)          
  C5     0.4784 (3)     0.8173 (4)      0.07370 (18)    0.0809 (10)          
  H5     0.4966         0.8596          0.0389          0.097\*              
  C6     0.4693 (2)     0.6812 (3)      0.07553 (14)    0.0651 (8)           
  H6     0.4812         0.6311          0.0418          0.078\*              
  C7     0.67271 (19)   0.4424 (2)      0.12844 (10)    0.0406 (6)           
  C8     0.7020 (2)     0.3589 (2)      0.08434 (11)    0.0440 (6)           
  H8     0.6593         0.2804          0.0761          0.053\*              
  C9     0.7967 (2)     0.3923 (2)      0.05159 (11)    0.0426 (6)           
  C10    0.8574 (2)     0.5106 (2)      0.06549 (11)    0.0480 (6)           
  H10    0.9176         0.5362          0.0428          0.058\*              
  C11    0.8311 (2)     0.5919 (2)      0.11203 (11)    0.0462 (6)           
  H11    0.8754         0.6690          0.1213          0.055\*              
  C12    0.7384 (2)     0.5579 (2)      0.14468 (11)    0.0425 (6)           
  C13    0.7683 (3)     0.7483 (3)      0.20859 (15)    0.0705 (9)           
  H13A   0.8534         0.7307          0.2222          0.106\*              
  H13B   0.7334         0.7898          0.2409          0.106\*              
  H13C   0.7602         0.8058          0.1738          0.106\*              
  C14    0.8334 (2)     0.3028 (3)      0.00548 (11)    0.0479 (6)           
  H14    0.8762         0.3361          −0.0242         0.057\*              
  C15    0.8452 (2)     0.0964 (2)      −0.03798 (11)   0.0426 (6)           
  C16    0.8973 (2)     0.1298 (2)      −0.09185 (11)   0.0464 (6)           
  C17    0.8386 (2)     −0.0375 (2)     −0.03448 (11)   0.0454 (6)           
  C18    0.7882 (3)     −0.1191 (3)     0.01137 (13)    0.0641 (8)           
  H18A   0.7636         −0.0631         0.0422          0.096\*              
  H18B   0.8497         −0.1794         0.0299          0.096\*              
  H18C   0.7188         −0.1676         −0.0083         0.096\*              
  C19    0.8505 (3)     −0.2198 (3)     −0.10901 (15)   0.0740 (9)           
  H19A   0.8321         −0.2801         −0.0783         0.111\*              
  H19B   0.9152         −0.2551         −0.1285         0.111\*              
  H19C   0.7790         −0.2070         −0.1389         0.111\*              
  C20    0.9860 (2)     −0.0126 (2)     −0.16676 (11)   0.0464 (6)           
  C21    1.0877 (2)     −0.0934 (3)     −0.15858 (13)   0.0590 (7)           
  H21    1.1128         −0.1339         −0.1212         0.071\*              
  C22    1.1517 (3)     −0.1131 (3)     −0.20709 (15)   0.0713 (9)           
  H22    1.2197         −0.1681         −0.2022         0.086\*              
  C23    1.1156 (3)     −0.0521 (3)     −0.26230 (15)   0.0746 (10)          
  H23    1.1578         −0.0676         −0.2949         0.090\*              
  C24    1.0169 (3)     0.0320 (3)      −0.26911 (13)   0.0698 (9)           
  H24    0.9948         0.0764          −0.3058         0.084\*              
  C25    0.9499 (2)     0.0510 (3)      −0.22172 (12)   0.0581 (7)           
  H25    0.8817         0.1057          −0.2268         0.070\*              
  ------ -------------- --------------- --------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Cl1   0.1248 (9)    0.0543 (6)    0.2232 (15)   0.0018 (5)     −0.0119 (9)    0.0116 (7)
  S1    0.0484 (4)    0.0558 (5)    0.0687 (5)    −0.0162 (3)    0.0215 (3)     −0.0118 (3)
  N1    0.0461 (11)   0.0448 (13)   0.0460 (12)   −0.0022 (10)   0.0092 (9)     −0.0025 (9)
  N2    0.0614 (13)   0.0431 (12)   0.0546 (14)   −0.0067 (10)   0.0239 (11)    −0.0020 (10)
  N3    0.0568 (12)   0.0386 (12)   0.0500 (12)   −0.0078 (10)   0.0156 (10)    −0.0030 (9)
  O1    0.0710 (13)   0.0767 (14)   0.0990 (16)   −0.0271 (11)   0.0480 (12)    −0.0073 (12)
  O2    0.0650 (12)   0.0821 (15)   0.0712 (14)   −0.0193 (10)   0.0095 (10)    −0.0306 (11)
  O3    0.0537 (10)   0.0459 (10)   0.0535 (11)   −0.0081 (8)    0.0208 (8)     0.0004 (8)
  O4    0.0549 (11)   0.0530 (11)   0.0576 (11)   −0.0096 (8)    0.0124 (9)     −0.0172 (8)
  O5    0.0811 (13)   0.0442 (11)   0.0669 (13)   −0.0084 (9)    0.0345 (11)    0.0020 (9)
  C1    0.0391 (14)   0.0532 (16)   0.0631 (17)   −0.0016 (11)   0.0102 (12)    −0.0045 (13)
  C2    0.0656 (18)   0.065 (2)     0.083 (2)     −0.0015 (16)   0.0242 (16)    −0.0099 (17)
  C3    0.073 (2)     0.066 (2)     0.111 (3)     0.0068 (17)    0.010 (2)      −0.026 (2)
  C4    0.0586 (19)   0.058 (2)     0.126 (3)     0.0053 (16)    −0.006 (2)     0.009 (2)
  C5    0.067 (2)     0.073 (2)     0.099 (3)     0.0016 (17)    −0.0010 (19)   0.026 (2)
  C6    0.0547 (17)   0.069 (2)     0.069 (2)     0.0006 (14)    −0.0002 (14)   0.0035 (15)
  C7    0.0411 (13)   0.0379 (13)   0.0448 (14)   −0.0021 (10)   0.0125 (11)    0.0016 (10)
  C8    0.0463 (13)   0.0356 (13)   0.0512 (15)   −0.0052 (11)   0.0111 (11)    0.0004 (11)
  C9    0.0453 (13)   0.0372 (13)   0.0469 (14)   −0.0023 (11)   0.0122 (11)    0.0010 (10)
  C10   0.0462 (14)   0.0453 (15)   0.0558 (16)   −0.0061 (11)   0.0184 (12)    0.0029 (12)
  C11   0.0426 (13)   0.0395 (14)   0.0560 (16)   −0.0081 (11)   0.0061 (11)    −0.0025 (11)
  C12   0.0423 (14)   0.0383 (13)   0.0458 (14)   0.0016 (11)    0.0034 (11)    −0.0020 (11)
  C13   0.0780 (19)   0.0533 (18)   0.081 (2)     −0.0145 (15)   0.0125 (16)    −0.0280 (15)
  C14   0.0472 (14)   0.0502 (16)   0.0491 (15)   −0.0022 (12)   0.0163 (12)    −0.0024 (12)
  C15   0.0400 (13)   0.0410 (14)   0.0476 (14)   −0.0054 (11)   0.0095 (11)    −0.0009 (11)
  C16   0.0429 (13)   0.0451 (15)   0.0530 (15)   −0.0036 (11)   0.0131 (11)    −0.0041 (12)
  C17   0.0429 (14)   0.0480 (15)   0.0462 (15)   −0.0034 (11)   0.0098 (11)    0.0003 (11)
  C18   0.080 (2)     0.0533 (17)   0.0636 (19)   −0.0114 (14)   0.0245 (16)    0.0040 (14)
  C19   0.094 (2)     0.0513 (18)   0.083 (2)     −0.0229 (16)   0.0352 (19)    −0.0200 (16)
  C20   0.0508 (15)   0.0472 (15)   0.0439 (14)   −0.0112 (12)   0.0153 (11)    −0.0061 (11)
  C21   0.0636 (17)   0.0621 (18)   0.0544 (17)   0.0006 (14)    0.0187 (14)    −0.0044 (13)
  C22   0.072 (2)     0.071 (2)     0.078 (2)     0.0013 (16)    0.0342 (17)    −0.0096 (17)
  C23   0.090 (2)     0.080 (2)     0.063 (2)     −0.0271 (19)   0.0385 (18)    −0.0237 (17)
  C24   0.089 (2)     0.078 (2)     0.0429 (16)   −0.0328 (19)   0.0130 (15)    −0.0034 (14)
  C25   0.0553 (16)   0.0638 (19)   0.0547 (17)   −0.0154 (13)   0.0066 (13)    −0.0030 (14)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ----------------- ------------- ------------------- -----------
  Cl1---C4          1.743 (3)     C9---C10            1.388 (3)
  S1---O1           1.4218 (18)   C9---C14            1.470 (3)
  S1---O2           1.4263 (19)   C10---C11           1.386 (3)
  S1---O3           1.6055 (18)   C10---H10           0.9300
  S1---C1           1.760 (3)     C11---C12           1.385 (3)
  N1---C14          1.267 (3)     C11---H11           0.9300
  N1---C15          1.397 (3)     C13---H13A          0.9600
  N2---C16          1.391 (3)     C13---H13B          0.9600
  N2---N3           1.404 (3)     C13---H13C          0.9600
  N2---C20          1.428 (3)     C14---H14           0.9300
  N3---C17          1.365 (3)     C15---C17           1.365 (3)
  N3---C19          1.453 (3)     C15---C16           1.443 (3)
  O3---C7           1.414 (2)     C17---C18           1.484 (3)
  O4---C12          1.357 (3)     C18---H18A          0.9600
  O4---C13          1.434 (3)     C18---H18B          0.9600
  O5---C16          1.241 (3)     C18---H18C          0.9600
  C1---C2           1.379 (4)     C19---H19A          0.9600
  C1---C6           1.379 (4)     C19---H19B          0.9600
  C2---C3           1.386 (4)     C19---H19C          0.9600
  C2---H2           0.9300        C20---C21           1.381 (4)
  C3---C4           1.379 (5)     C20---C25           1.383 (3)
  C3---H3           0.9300        C21---C22           1.389 (3)
  C4---C5           1.371 (5)     C21---H21           0.9300
  C5---C6           1.386 (5)     C22---C23           1.375 (4)
  C5---H5           0.9300        C22---H22           0.9300
  C6---H6           0.9300        C23---C24           1.377 (4)
  C7---C8           1.370 (3)     C23---H23           0.9300
  C7---C12          1.397 (3)     C24---C25           1.388 (4)
  C8---C9           1.404 (3)     C24---H24           0.9300
  C8---H8           0.9300        C25---H25           0.9300
                                                      
  O1---S1---O2      120.58 (13)   C11---C12---C7      118.2 (2)
  O1---S1---O3      102.82 (12)   O4---C13---H13A     109.5
  O2---S1---O3      108.64 (11)   O4---C13---H13B     109.5
  O1---S1---C1      110.01 (12)   H13A---C13---H13B   109.5
  O2---S1---C1      109.40 (14)   O4---C13---H13C     109.5
  O3---S1---C1      103.96 (10)   H13A---C13---H13C   109.5
  C14---N1---C15    120.9 (2)     H13B---C13---H13C   109.5
  C16---N2---N3     110.16 (19)   N1---C14---C9       121.3 (2)
  C16---N2---C20    125.9 (2)     N1---C14---H14      119.4
  N3---N2---C20     121.39 (19)   C9---C14---H14      119.4
  C17---N3---N2     106.35 (19)   C17---C15---N1      123.4 (2)
  C17---N3---C19    124.7 (2)     C17---C15---C16     108.2 (2)
  N2---N3---C19     118.2 (2)     N1---C15---C16      128.3 (2)
  C7---O3---S1      117.31 (14)   O5---C16---N2       123.7 (2)
  C12---O4---C13    117.80 (19)   O5---C16---C15      131.8 (2)
  C2---C1---C6      121.2 (3)     N2---C16---C15      104.4 (2)
  C2---C1---S1      119.3 (2)     C15---C17---N3      110.3 (2)
  C6---C1---S1      119.4 (2)     C15---C17---C18     128.6 (2)
  C1---C2---C3      119.4 (3)     N3---C17---C18      121.1 (2)
  C1---C2---H2      120.3         C17---C18---H18A    109.5
  C3---C2---H2      120.3         C17---C18---H18B    109.5
  C4---C3---C2      118.9 (3)     H18A---C18---H18B   109.5
  C4---C3---H3      120.6         C17---C18---H18C    109.5
  C2---C3---H3      120.6         H18A---C18---H18C   109.5
  C5---C4---C3      122.2 (3)     H18B---C18---H18C   109.5
  C5---C4---Cl1     119.1 (3)     N3---C19---H19A     109.5
  C3---C4---Cl1     118.7 (3)     N3---C19---H19B     109.5
  C4---C5---C6      118.7 (3)     H19A---C19---H19B   109.5
  C4---C5---H5      120.6         N3---C19---H19C     109.5
  C6---C5---H5      120.6         H19A---C19---H19C   109.5
  C1---C6---C5      119.6 (3)     H19B---C19---H19C   109.5
  C1---C6---H6      120.2         C21---C20---C25     120.9 (2)
  C5---C6---H6      120.2         C21---C20---N2      121.2 (2)
  C8---C7---C12     122.3 (2)     C25---C20---N2      117.9 (2)
  C8---C7---O3      119.9 (2)     C20---C21---C22     119.0 (3)
  C12---C7---O3     117.74 (19)   C20---C21---H21     120.5
  C7---C8---C9      119.7 (2)     C22---C21---H21     120.5
  C7---C8---H8      120.2         C23---C22---C21     120.7 (3)
  C9---C8---H8      120.2         C23---C22---H22     119.7
  C10---C9---C8     117.9 (2)     C21---C22---H22     119.7
  C10---C9---C14    121.0 (2)     C22---C23---C24     119.7 (3)
  C8---C9---C14     121.1 (2)     C22---C23---H23     120.2
  C11---C10---C9    122.1 (2)     C24---C23---H23     120.2
  C11---C10---H10   118.9         C23---C24---C25     120.6 (3)
  C9---C10---H10    118.9         C23---C24---H24     119.7
  C12---C11---C10   119.7 (2)     C25---C24---H24     119.7
  C12---C11---H11   120.1         C20---C25---C24     119.0 (3)
  C10---C11---H11   120.1         C20---C25---H25     120.5
  O4---C12---C11    125.5 (2)     C24---C25---H25     120.5
  O4---C12---C7     116.35 (19)                       
  ----------------- ------------- ------------------- -----------

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

  ------------------- --------- --------- ----------- ---------------
  *D*---H···*A*       *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C11---H11···O5^i^   0.93      2.43      3.199 (3)   140
  ------------------- --------- --------- ----------- ---------------

Symmetry code: (i) −*x*+2, −*y*+1, −*z*.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*       *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ----------------- --------- ------- ----------- -------------
  C11---H11⋯O5^i^   0.93      2.43    3.199 (3)   140

Symmetry code: (i) .
