Co-crystallization of 3,5-di­nitro­benzoic acid with two anti­psychotic agents: a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O—H...O hydrogen bond with chlorprothixene

Co-crystallization of 3,5-di­nitro­benzoic acid with trihexyphenidyl [or 1-cyclo­hexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol], gives a 1:1 salt (I) but chlorprothixene [or (Z)-3-(2-chloro-9H-thioxanthen-9-yl)-N,N-di­methyl­propan-1-amine], gives a 1:2 acid salt (II) containing a very short O—H...O hydrogen bond. Multiple hydrogen bonds link the ions in (I) into a complex chain of rings and those in (II) link the ions into a sheet.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.109
• Data-to-parameter ratio = 16.2

Structure: II

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.098
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.976 Why?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.6 Note
PLAT411_ALERT_2_C Short Inter H...H Contact  H22A     ..H44      .       2.14 Ang.
                                                 1-x,-y,1-z  =      2_656 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        113 Report

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.61 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        324 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT355_ALERT_3_C Long   O-H (X0.82,N0.98A)  O312     - H312     .       1.04 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         15 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O212     ..C1               2.98 Ang.
                                                      x,y,z  =      1_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O311     ..C112             3.01 Ang.
                                                      x,y,z  =      1_555 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              C7 H4 N2 O6
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        144 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

1-(3-Cyclohexyl-3-hydroxy-3-phenylpropyl)piperidin-1-ium 3,5-dinitrobenzoate (I)

Crystal data

C20H32NO^+·C7H3N2O6^−	Z = 2
Mr = 513.58	F(000) = 548
Triclinic, P1	Dx = 1.315 Mg m^−3
a = 11.2743 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2898 (12) Å	Cell parameters from 5525 reflections
c = 12.6478 (13) Å	θ = 2.0–27.5°
α = 111.923 (1)°	µ = 0.10 mm^−1
β = 114.325 (1)°	T = 173 K
γ = 95.903 (1)°	Plate, colourless
V = 1296.6 (2) Å^3	0.61 × 0.58 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer	5525 independent reflections
Radiation source: fine focus sealed tube	4819 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 0.3333 pixels mm^-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −7→14
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −14→13
Tmin = 0.944, Tmax = 0.988	l = −16→15
7191 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 0.3666P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
5525 reflections	Δρmax = 0.32 e Å^−3
340 parameters	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.12573 (11)	0.36273 (11)	0.26416 (10)	0.0190 (2)
O1	0.21852 (9)	0.39505 (9)	0.39566 (8)	0.0248 (2)
H1	0.2717 (18)	0.3492 (17)	0.3928 (16)	0.037*
C2	0.19972 (12)	0.32806 (11)	0.18280 (11)	0.0208 (2)
H2A	0.2296	0.2489	0.1838	0.025*
H2B	0.1354	0.3047	0.0911	0.025*
C3	0.32358 (12)	0.44489 (12)	0.23607 (12)	0.0225 (2)
H3A	0.2942	0.5043	0.1959	0.027*
H3B	0.3615	0.4976	0.3315	0.027*
C11	0.07862 (11)	0.48561 (11)	0.26615 (11)	0.0199 (2)
C12	−0.00040 (13)	0.48954 (13)	0.14936 (12)	0.0266 (3)
H12	−0.0193	0.4184	0.0688	0.032*
C13	−0.05172 (14)	0.59666 (15)	0.14980 (14)	0.0329 (3)
H13	−0.1029	0.5994	0.0699	0.039*
C14	−0.02874 (15)	0.69892 (14)	0.26556 (15)	0.0343 (3)
H14	−0.0662	0.7705	0.2652	0.041*
C15	0.04917 (14)	0.69630 (13)	0.38178 (14)	0.0312 (3)
H15	0.0659	0.7667	0.4618	0.037*
C16	0.10342 (13)	0.59084 (12)	0.38237 (12)	0.0262 (3)
H16	0.1580	0.5908	0.4630	0.031*
C21	−0.00168 (12)	0.24305 (11)	0.20637 (11)	0.0213 (2)
H21	−0.0682	0.2300	0.1179	0.026*
C22	0.03208 (14)	0.11178 (13)	0.19039 (14)	0.0304 (3)
H22A	0.1027	0.1243	0.2761	0.037*
H22B	0.0703	0.0885	0.1301	0.037*
C23	−0.09347 (16)	−0.00389 (13)	0.13718 (15)	0.0358 (3)
H23A	−0.1593	−0.0241	0.0468	0.043*
H23B	−0.0654	−0.0848	0.1343	0.043*
C24	−0.16323 (16)	0.02887 (14)	0.22054 (15)	0.0373 (3)
H24A	−0.2476	−0.0453	0.1795	0.045*
H24B	−0.1018	0.0384	0.3080	0.045*
C25	−0.19849 (15)	0.15810 (14)	0.23433 (16)	0.0373 (3)
H25A	−0.2393	0.1807	0.2925	0.045*
H25B	−0.2670	0.1454	0.1477	0.045*
C26	−0.07169 (14)	0.27333 (13)	0.29049 (14)	0.0295 (3)
H26A	−0.0063	0.2902	0.3798	0.035*
H26B	−0.0982	0.3556	0.2967	0.035*
N31	0.43308 (10)	0.39959 (10)	0.20951 (9)	0.0199 (2)
H31	0.4499 (14)	0.3329 (15)	0.2365 (14)	0.024*
C32	0.39085 (13)	0.33636 (15)	0.06744 (12)	0.0297 (3)
H32A	0.3700	0.4022	0.0337	0.036*
H32B	0.3070	0.2594	0.0189	0.036*
C33	0.50410 (14)	0.28851 (17)	0.04548 (13)	0.0387 (3)
H33A	0.4756	0.2497	−0.0487	0.046*
H33B	0.5196	0.2174	0.0728	0.046*
C34	0.63655 (15)	0.40357 (17)	0.12266 (15)	0.0400 (3)
H34A	0.7101	0.3692	0.1114	0.048*
H34B	0.6241	0.4705	0.0893	0.048*
C35	0.67691 (14)	0.46939 (15)	0.26640 (14)	0.0349 (3)
H35A	0.6995	0.4051	0.3019	0.042*
H35B	0.7594	0.5478	0.3149	0.042*
C36	0.56213 (13)	0.51417 (13)	0.28592 (13)	0.0314 (3)
H36A	0.5894	0.5532	0.3798	0.038*
H36B	0.5455	0.5847	0.2580	0.038*
C41	0.57048 (12)	0.14707 (12)	0.45254 (12)	0.0236 (2)
C42	0.60720 (13)	0.19029 (12)	0.58292 (12)	0.0251 (3)
H42	0.5743	0.2571	0.6242	0.030*
C43	0.69222 (13)	0.13517 (12)	0.65226 (12)	0.0260 (3)
C44	0.73907 (13)	0.03474 (13)	0.59588 (13)	0.0273 (3)
H44	0.7981	−0.0018	0.6448	0.033*
C45	0.69577 (13)	−0.00984 (12)	0.46483 (12)	0.0246 (3)
C46	0.61418 (12)	0.04496 (12)	0.39155 (12)	0.0231 (2)
H46	0.5889	0.0134	0.3020	0.028*
C411	0.48388 (14)	0.21494 (13)	0.37987 (13)	0.0298 (3)
O411	0.48586 (11)	0.20351 (11)	0.27857 (10)	0.0394 (3)
O412	0.42093 (13)	0.27683 (14)	0.42999 (11)	0.0571 (4)
N43	0.73412 (14)	0.18513 (13)	0.79160 (12)	0.0387 (3)
O431	0.68879 (14)	0.27080 (13)	0.83989 (11)	0.0555 (3)
O432	0.81408 (17)	0.13945 (15)	0.85243 (12)	0.0690 (4)
N45	0.73858 (13)	−0.12129 (12)	0.40094 (12)	0.0341 (3)
O451	0.83761 (16)	−0.14320 (16)	0.46933 (13)	0.0756 (5)
O452	0.67240 (12)	−0.18761 (10)	0.28288 (10)	0.0433 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0193 (5)	0.0205 (5)	0.0185 (5)	0.0088 (4)	0.0076 (4)	0.0113 (4)
O1	0.0246 (4)	0.0304 (5)	0.0200 (4)	0.0149 (4)	0.0079 (3)	0.0138 (3)
C2	0.0215 (6)	0.0198 (5)	0.0226 (5)	0.0083 (4)	0.0106 (4)	0.0109 (4)
C3	0.0228 (6)	0.0197 (5)	0.0284 (6)	0.0097 (5)	0.0135 (5)	0.0122 (5)
C11	0.0186 (5)	0.0205 (5)	0.0254 (6)	0.0078 (4)	0.0111 (5)	0.0141 (4)
C12	0.0270 (6)	0.0309 (6)	0.0272 (6)	0.0139 (5)	0.0129 (5)	0.0177 (5)
C13	0.0325 (7)	0.0411 (8)	0.0423 (7)	0.0212 (6)	0.0195 (6)	0.0317 (6)
C14	0.0382 (8)	0.0309 (7)	0.0569 (9)	0.0223 (6)	0.0311 (7)	0.0305 (7)
C15	0.0370 (7)	0.0220 (6)	0.0412 (7)	0.0119 (5)	0.0243 (6)	0.0141 (5)
C16	0.0285 (6)	0.0233 (6)	0.0277 (6)	0.0098 (5)	0.0133 (5)	0.0126 (5)
C21	0.0220 (6)	0.0211 (6)	0.0241 (5)	0.0081 (5)	0.0109 (5)	0.0134 (4)
C22	0.0348 (7)	0.0226 (6)	0.0418 (7)	0.0121 (5)	0.0234 (6)	0.0163 (5)
C23	0.0438 (8)	0.0223 (6)	0.0441 (8)	0.0077 (6)	0.0258 (7)	0.0136 (6)
C24	0.0436 (8)	0.0274 (7)	0.0463 (8)	0.0052 (6)	0.0271 (7)	0.0179 (6)
C25	0.0354 (8)	0.0332 (7)	0.0540 (9)	0.0105 (6)	0.0295 (7)	0.0216 (6)
C26	0.0325 (7)	0.0246 (6)	0.0402 (7)	0.0108 (5)	0.0238 (6)	0.0159 (5)
N31	0.0189 (5)	0.0217 (5)	0.0220 (5)	0.0080 (4)	0.0092 (4)	0.0132 (4)
C32	0.0229 (6)	0.0426 (7)	0.0208 (6)	0.0083 (5)	0.0083 (5)	0.0148 (5)
C33	0.0294 (7)	0.0573 (9)	0.0252 (6)	0.0126 (7)	0.0154 (6)	0.0127 (6)
C34	0.0297 (7)	0.0611 (10)	0.0410 (8)	0.0148 (7)	0.0222 (6)	0.0290 (7)
C35	0.0204 (6)	0.0411 (8)	0.0362 (7)	0.0053 (6)	0.0116 (5)	0.0146 (6)
C36	0.0225 (6)	0.0275 (6)	0.0341 (7)	0.0025 (5)	0.0112 (5)	0.0087 (5)
C41	0.0199 (6)	0.0206 (5)	0.0314 (6)	0.0074 (5)	0.0102 (5)	0.0154 (5)
C42	0.0256 (6)	0.0197 (6)	0.0322 (6)	0.0090 (5)	0.0146 (5)	0.0131 (5)
C43	0.0297 (6)	0.0236 (6)	0.0273 (6)	0.0083 (5)	0.0137 (5)	0.0144 (5)
C44	0.0305 (7)	0.0274 (6)	0.0321 (6)	0.0144 (5)	0.0148 (5)	0.0205 (5)
C45	0.0264 (6)	0.0221 (6)	0.0329 (6)	0.0120 (5)	0.0162 (5)	0.0169 (5)
C46	0.0228 (6)	0.0215 (6)	0.0279 (6)	0.0077 (5)	0.0116 (5)	0.0149 (5)
C411	0.0291 (7)	0.0258 (6)	0.0328 (7)	0.0148 (5)	0.0100 (5)	0.0158 (5)
O411	0.0495 (6)	0.0435 (6)	0.0468 (6)	0.0300 (5)	0.0264 (5)	0.0343 (5)
O412	0.0659 (8)	0.0780 (9)	0.0382 (6)	0.0600 (7)	0.0233 (6)	0.0298 (6)
N43	0.0522 (8)	0.0376 (7)	0.0314 (6)	0.0204 (6)	0.0202 (6)	0.0192 (5)
O431	0.0820 (9)	0.0577 (7)	0.0393 (6)	0.0412 (7)	0.0359 (6)	0.0222 (5)
O432	0.1064 (11)	0.0804 (9)	0.0373 (6)	0.0633 (9)	0.0315 (7)	0.0383 (6)
N45	0.0459 (7)	0.0346 (6)	0.0365 (6)	0.0258 (6)	0.0237 (6)	0.0231 (5)
O451	0.0945 (11)	0.1011 (11)	0.0485 (7)	0.0853 (10)	0.0330 (7)	0.0385 (7)
O452	0.0612 (7)	0.0328 (5)	0.0372 (6)	0.0235 (5)	0.0239 (5)	0.0151 (4)

Geometric parameters (Å, º)

C1—O1	1.4243 (13)	C26—H26A	0.9900
C1—C11	1.5310 (15)	C26—H26B	0.9900
C1—C2	1.5432 (16)	N31—C32	1.4941 (15)
C1—C21	1.5562 (16)	N31—C36	1.4984 (15)
O1—H1	0.834 (18)	N31—H31	0.942 (15)
C2—C3	1.5252 (16)	C32—C33	1.5236 (19)
C2—H2A	0.9900	C32—H32A	0.9900
C2—H2B	0.9900	C32—H32B	0.9900
C3—N31	1.4972 (15)	C33—C34	1.524 (2)
C3—H3A	0.9900	C33—H33A	0.9900
C3—H3B	0.9900	C33—H33B	0.9900
C11—C16	1.3926 (17)	C34—C35	1.518 (2)
C11—C12	1.3966 (16)	C34—H34A	0.9900
C12—C13	1.3924 (18)	C34—H34B	0.9900
C12—H12	0.9500	C35—C36	1.5151 (19)
C13—C14	1.381 (2)	C35—H35A	0.9900
C13—H13	0.9500	C35—H35B	0.9900
C14—C15	1.381 (2)	C36—H36A	0.9900
C14—H14	0.9500	C36—H36B	0.9900
C15—C16	1.3945 (18)	C41—C42	1.3870 (18)
C15—H15	0.9500	C41—C46	1.3902 (17)
C16—H16	0.9500	C41—C411	1.5250 (16)
C21—C22	1.5290 (16)	C42—C43	1.3831 (17)
C21—C26	1.5322 (17)	C42—H42	0.9500
C21—H21	1.0000	C43—C44	1.3794 (18)
C22—C23	1.5298 (19)	C43—N43	1.4712 (17)
C22—H22A	0.9900	C44—C45	1.3780 (18)
C22—H22B	0.9900	C44—H44	0.9500
C23—C24	1.523 (2)	C45—C46	1.3895 (16)
C23—H23A	0.9900	C45—N45	1.4684 (16)
C23—H23B	0.9900	C46—H46	0.9500
C24—C25	1.518 (2)	C411—O412	1.2392 (17)
C24—H24A	0.9900	C411—O411	1.2488 (17)
C24—H24B	0.9900	N43—O431	1.2195 (17)
C25—C26	1.5269 (18)	N43—O432	1.2211 (16)
C25—H25A	0.9900	N45—O451	1.2153 (16)
C25—H25B	0.9900	N45—O452	1.2163 (16)
O1—C1—C11	107.31 (9)	C25—C26—H26A	109.2
O1—C1—C2	109.01 (9)	C21—C26—H26A	109.2
C11—C1—C2	111.07 (9)	C25—C26—H26B	109.2
O1—C1—C21	110.45 (9)	C21—C26—H26B	109.2
C11—C1—C21	108.41 (9)	H26A—C26—H26B	107.9
C2—C1—C21	110.55 (9)	C32—N31—C3	112.66 (9)
C1—O1—H1	106.8 (11)	C32—N31—C36	110.68 (10)
C3—C2—C1	111.54 (9)	C3—N31—C36	110.31 (9)
C3—C2—H2A	109.3	C32—N31—H31	106.4 (9)
C1—C2—H2A	109.3	C3—N31—H31	107.9 (9)
C3—C2—H2B	109.3	C36—N31—H31	108.8 (9)
C1—C2—H2B	109.3	N31—C32—C33	110.53 (10)
H2A—C2—H2B	108.0	N31—C32—H32A	109.5
N31—C3—C2	112.50 (9)	C33—C32—H32A	109.5
N31—C3—H3A	109.1	N31—C32—H32B	109.5
C2—C3—H3A	109.1	C33—C32—H32B	109.5
N31—C3—H3B	109.1	H32A—C32—H32B	108.1
C2—C3—H3B	109.1	C32—C33—C34	111.08 (13)
H3A—C3—H3B	107.8	C32—C33—H33A	109.4
C16—C11—C12	118.22 (11)	C34—C33—H33A	109.4
C16—C11—C1	121.30 (10)	C32—C33—H33B	109.4
C12—C11—C1	120.27 (11)	C34—C33—H33B	109.4
C13—C12—C11	120.64 (12)	H33A—C33—H33B	108.0
C13—C12—H12	119.7	C35—C34—C33	109.98 (11)
C11—C12—H12	119.7	C35—C34—H34A	109.7
C14—C13—C12	120.50 (12)	C33—C34—H34A	109.7
C14—C13—H13	119.8	C35—C34—H34B	109.7
C12—C13—H13	119.8	C33—C34—H34B	109.7
C13—C14—C15	119.46 (12)	H34A—C34—H34B	108.2
C13—C14—H14	120.3	C36—C35—C34	110.94 (11)
C15—C14—H14	120.3	C36—C35—H35A	109.5
C14—C15—C16	120.36 (13)	C34—C35—H35A	109.5
C14—C15—H15	119.8	C36—C35—H35B	109.5
C16—C15—H15	119.8	C34—C35—H35B	109.5
C11—C16—C15	120.79 (12)	H35A—C35—H35B	108.0
C11—C16—H16	119.6	N31—C36—C35	111.39 (11)
C15—C16—H16	119.6	N31—C36—H36A	109.3
C22—C21—C26	109.28 (10)	C35—C36—H36A	109.3
C22—C21—C1	112.90 (10)	N31—C36—H36B	109.3
C26—C21—C1	111.07 (10)	C35—C36—H36B	109.3
C22—C21—H21	107.8	H36A—C36—H36B	108.0
C26—C21—H21	107.8	C42—C41—C46	119.83 (11)
C1—C21—H21	107.8	C42—C41—C411	118.64 (11)
C21—C22—C23	112.23 (11)	C46—C41—C411	121.53 (11)
C21—C22—H22A	109.2	C43—C42—C41	119.35 (11)
C23—C22—H22A	109.2	C43—C42—H42	120.3
C21—C22—H22B	109.2	C41—C42—H42	120.3
C23—C22—H22B	109.2	C44—C43—C42	122.62 (12)
H22A—C22—H22B	107.9	C44—C43—N43	118.58 (11)
C24—C23—C22	112.00 (12)	C42—C43—N43	118.80 (12)
C24—C23—H23A	109.2	C45—C44—C43	116.45 (11)
C22—C23—H23A	109.2	C45—C44—H44	121.8
C24—C23—H23B	109.2	C43—C44—H44	121.8
C22—C23—H23B	109.2	C44—C45—C46	123.31 (12)
H23A—C23—H23B	107.9	C44—C45—N45	117.53 (11)
C25—C24—C23	110.25 (12)	C46—C45—N45	119.15 (11)
C25—C24—H24A	109.6	C45—C46—C41	118.33 (11)
C23—C24—H24A	109.6	C45—C46—H46	120.8
C25—C24—H24B	109.6	C41—C46—H46	120.8
C23—C24—H24B	109.6	O412—C411—O411	127.63 (12)
H24A—C24—H24B	108.1	O412—C411—C41	115.60 (12)
C24—C25—C26	111.10 (12)	O411—C411—C41	116.77 (11)
C24—C25—H25A	109.4	O431—N43—O432	123.94 (13)
C26—C25—H25A	109.4	O431—N43—C43	118.29 (12)
C24—C25—H25B	109.4	O432—N43—C43	117.76 (12)
C26—C25—H25B	109.4	O451—N45—O452	123.51 (13)
H25A—C25—H25B	108.0	O451—N45—C45	118.05 (12)
C25—C26—C21	111.98 (11)	O452—N45—C45	118.43 (11)
O1—C1—C2—C3	−59.48 (12)	C2—C3—N31—C36	−168.65 (10)
C11—C1—C2—C3	58.55 (12)	C3—N31—C32—C33	−178.36 (11)
C21—C1—C2—C3	178.93 (9)	C36—N31—C32—C33	57.61 (14)
C1—C2—C3—N31	151.06 (9)	N31—C32—C33—C34	−57.20 (16)
O1—C1—C11—C16	−13.05 (15)	C32—C33—C34—C35	55.72 (17)
C2—C1—C11—C16	−132.11 (11)	C33—C34—C35—C36	−55.20 (17)
C21—C1—C11—C16	106.24 (12)	C32—N31—C36—C35	−57.67 (14)
O1—C1—C11—C12	172.21 (10)	C3—N31—C36—C35	176.97 (10)
C2—C1—C11—C12	53.16 (14)	C34—C35—C36—N31	56.62 (16)
C21—C1—C11—C12	−68.49 (13)	C46—C41—C42—C43	2.93 (18)
C16—C11—C12—C13	0.57 (19)	C411—C41—C42—C43	−176.29 (11)
C1—C11—C12—C13	175.46 (12)	C41—C42—C43—C44	−2.27 (19)
C11—C12—C13—C14	−2.0 (2)	C41—C42—C43—N43	177.95 (11)
C12—C13—C14—C15	1.9 (2)	C42—C43—C44—C45	−0.52 (19)
C13—C14—C15—C16	−0.5 (2)	N43—C43—C44—C45	179.25 (12)
C12—C11—C16—C15	0.85 (18)	C43—C44—C45—C46	2.75 (19)
C1—C11—C16—C15	−173.99 (11)	C43—C44—C45—N45	−177.01 (11)
C14—C15—C16—C11	−0.9 (2)	C44—C45—C46—C41	−2.10 (19)
O1—C1—C21—C22	−66.93 (13)	N45—C45—C46—C41	177.65 (11)
C11—C1—C21—C22	175.76 (10)	C42—C41—C46—C45	−0.84 (18)
C2—C1—C21—C22	53.80 (12)	C411—C41—C46—C45	178.36 (11)
O1—C1—C21—C26	56.22 (12)	C42—C41—C411—O412	−19.47 (18)
C11—C1—C21—C26	−61.08 (12)	C46—C41—C411—O412	161.32 (13)
C2—C1—C21—C26	176.96 (9)	C42—C41—C411—O411	159.59 (12)
C26—C21—C22—C23	54.22 (15)	C46—C41—C411—O411	−19.62 (18)
C1—C21—C22—C23	178.36 (10)	C44—C43—N43—O431	−177.62 (14)
C21—C22—C23—C24	−55.07 (16)	C42—C43—N43—O431	2.2 (2)
C22—C23—C24—C25	54.99 (17)	C44—C43—N43—O432	3.4 (2)
C23—C24—C25—C26	−56.14 (17)	C42—C43—N43—O432	−176.77 (14)
C24—C25—C26—C21	57.78 (15)	C44—C45—N45—O451	−20.5 (2)
C22—C21—C26—C25	−55.75 (14)	C46—C45—N45—O451	159.71 (14)
C1—C21—C26—C25	179.04 (10)	C44—C45—N45—O452	158.66 (13)
C2—C3—N31—C32	67.11 (12)	C46—C45—N45—O452	−21.11 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O412	0.84 (2)	1.91 (2)	2.724 (2)	165.9 (16)
N31—H31···O411	0.942 (18)	1.762 (18)	2.7026 (18)	175.7 (14)
C33—H33A···O452^i	0.99	2.49	3.4202 (17)	157
C36—H36A···O1^ii	0.99	2.56	3.4025 (16)	144
C36—H36A···O412^ii	0.99	2.51	3.3949 (19)	148

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

(Z)-3-(2-Chloro-9H-thioxanthen-9-yl)-N,N-dimethylpropan-1-aminium hydrogen bis(3,5-dinitrobenzoate) (II)

Crystal data

C18H19ClNS^+·C7H3N2O6^−·C7H4N2O6	F(000) = 1528
Mr = 740.09	Dx = 1.534 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3454 (8) Å	Cell parameters from 7139 reflections
b = 24.3857 (16) Å	θ = 1.8–27.4°
c = 11.6098 (8) Å	µ = 0.26 mm^−1
β = 93.691 (1)°	T = 173 K
V = 3205.4 (4) Å^3	Block, colourless
Z = 4	0.57 × 0.32 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer	7139 independent reflections
Radiation source: fine focus sealed tube	6365 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 0.3333 pixels mm^-1	θmax = 27.4°, θmin = 1.8°
φ and ω scans	h = −14→10
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −31→29
Tmin = 0.866, Tmax = 0.927	l = −14→14
17539 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 1.3713P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
7139 reflections	Δρmax = 0.53 e Å^−3
469 parameters	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.46269 (10)	0.12939 (5)	0.57731 (10)	0.0223 (2)
H1	0.4447 (15)	0.1572 (7)	0.6191 (15)	0.027*
C1	0.38593 (12)	0.13344 (6)	0.46761 (12)	0.0246 (3)
H1A	0.3964	0.0999	0.4214	0.029*
H1B	0.4126	0.1650	0.4223	0.029*
C2	0.25502 (12)	0.14048 (6)	0.48634 (12)	0.0261 (3)
H2A	0.2230	0.1063	0.5182	0.031*
H2B	0.2439	0.1706	0.5418	0.031*
C3	0.19115 (12)	0.15364 (6)	0.37157 (12)	0.0245 (3)
H4	0.2297	0.1786	0.3237	0.029*
C11	−0.01624 (12)	0.11072 (5)	0.50768 (12)	0.0239 (3)
H11	0.0195	0.1416	0.5457	0.029*
C12	−0.09218 (12)	0.07758 (6)	0.56502 (12)	0.0262 (3)
Cl12	−0.12220 (4)	0.09270 (2)	0.70590 (3)	0.03840 (11)
C13	−0.14546 (13)	0.03194 (6)	0.51215 (14)	0.0295 (3)
H13	−0.1956	0.0089	0.5533	0.035*
C14	−0.12428 (13)	0.02074 (6)	0.39893 (13)	0.0291 (3)
H14	−0.1610	−0.0100	0.3615	0.035*
C14A	−0.04963 (12)	0.05410 (5)	0.33893 (12)	0.0242 (3)
C14B	−0.01152 (12)	0.10620 (6)	0.13901 (12)	0.0244 (3)
C15	−0.04959 (12)	0.11668 (7)	0.02414 (12)	0.0290 (3)
H15	−0.0848	0.0883	−0.0223	0.035*
C16	−0.03588 (13)	0.16844 (7)	−0.02156 (13)	0.0319 (3)
H16	−0.0612	0.1756	−0.0997	0.038*
C17	0.01496 (13)	0.21007 (7)	0.04673 (13)	0.0319 (3)
H17	0.0233	0.2458	0.0155	0.038*
C18	0.05355 (12)	0.19964 (6)	0.16036 (12)	0.0275 (3)
H18	0.0880	0.2284	0.2063	0.033*
C18A	0.04245 (11)	0.14727 (6)	0.20842 (11)	0.0228 (3)
C18B	0.00798 (11)	0.09882 (5)	0.39387 (12)	0.0218 (3)
C19	0.08673 (12)	0.13438 (5)	0.32901 (11)	0.0224 (3)
S10	−0.02859 (4)	0.03901 (2)	0.19275 (3)	0.03131 (10)
C111	0.58939 (13)	0.13566 (7)	0.55300 (14)	0.0342 (3)
H11A	0.6382	0.1352	0.6258	0.051*
H11B	0.6005	0.1705	0.5132	0.051*
H11C	0.6128	0.1053	0.5040	0.051*
C112	0.44364 (15)	0.07721 (6)	0.63983 (13)	0.0339 (3)
H11D	0.4597	0.0461	0.5897	0.051*
H11E	0.3617	0.0754	0.6615	0.051*
H11F	0.4971	0.0757	0.7095	0.051*
C21	0.34839 (11)	0.33156 (5)	0.58695 (11)	0.0213 (3)
C22	0.29675 (12)	0.32558 (6)	0.47617 (12)	0.0235 (3)
H22	0.2962	0.2910	0.4383	0.028*
C23	0.24587 (12)	0.37130 (6)	0.42191 (12)	0.0246 (3)
C24	0.24301 (12)	0.42245 (6)	0.47285 (12)	0.0258 (3)
H24	0.2080	0.4532	0.4337	0.031*
C25	0.29399 (12)	0.42643 (6)	0.58389 (12)	0.0239 (3)
C26	0.34720 (11)	0.38231 (6)	0.64140 (12)	0.0226 (3)
H26	0.3825	0.3867	0.7173	0.027*
C211	0.40906 (11)	0.28301 (5)	0.64702 (11)	0.0222 (3)
O211	0.45673 (10)	0.29421 (4)	0.74604 (9)	0.0345 (3)
O212	0.40959 (10)	0.23880 (4)	0.59644 (9)	0.0335 (2)
N23	0.19402 (11)	0.36503 (6)	0.30332 (11)	0.0324 (3)
O231	0.18250 (13)	0.31902 (5)	0.26351 (10)	0.0515 (3)
O232	0.16581 (13)	0.40671 (5)	0.24991 (11)	0.0484 (3)
N25	0.29378 (11)	0.48001 (5)	0.64322 (12)	0.0314 (3)
O251	0.25334 (12)	0.51946 (5)	0.58850 (11)	0.0446 (3)
O252	0.33426 (12)	0.48210 (5)	0.74342 (11)	0.0454 (3)
C31	0.63540 (11)	0.17006 (6)	1.00227 (12)	0.0231 (3)
C32	0.70062 (12)	0.20569 (5)	1.07526 (12)	0.0235 (3)
H32	0.7188	0.2417	1.0504	0.028*
C33	0.73852 (12)	0.18786 (6)	1.18466 (12)	0.0251 (3)
C34	0.71344 (12)	0.13625 (6)	1.22519 (13)	0.0277 (3)
H34	0.7381	0.1250	1.3013	0.033*
C35	0.65054 (12)	0.10178 (6)	1.14944 (13)	0.0274 (3)
C36	0.61247 (12)	0.11696 (6)	1.03830 (13)	0.0255 (3)
H36	0.5716	0.0917	0.9878	0.031*
C311	0.57941 (12)	0.18953 (6)	0.88847 (12)	0.0248 (3)
O311	0.52336 (11)	0.15826 (5)	0.82386 (9)	0.0390 (3)
O312	0.59247 (10)	0.24171 (4)	0.87186 (9)	0.0317 (2)
H312	0.533 (3)	0.2576 (13)	0.808 (3)	0.099 (10)*
N33	0.80516 (11)	0.22598 (5)	1.26284 (11)	0.0321 (3)
O331	0.82007 (12)	0.27274 (5)	1.22899 (11)	0.0449 (3)
O332	0.84145 (11)	0.20876 (5)	1.35770 (10)	0.0441 (3)
N35	0.61594 (12)	0.04780 (5)	1.19234 (13)	0.0363 (3)
O351	0.62170 (13)	0.04108 (6)	1.29795 (12)	0.0563 (4)
O352	0.57984 (13)	0.01343 (5)	1.12204 (13)	0.0514 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0241 (6)	0.0184 (5)	0.0237 (6)	−0.0004 (4)	−0.0040 (4)	0.0005 (4)
C1	0.0263 (7)	0.0260 (7)	0.0207 (6)	−0.0005 (5)	−0.0043 (5)	0.0021 (5)
C2	0.0249 (7)	0.0294 (7)	0.0233 (7)	−0.0052 (5)	−0.0043 (5)	0.0028 (5)
C3	0.0239 (6)	0.0254 (7)	0.0239 (7)	−0.0021 (5)	−0.0022 (5)	0.0027 (5)
C11	0.0239 (7)	0.0202 (6)	0.0269 (7)	0.0015 (5)	−0.0040 (5)	0.0014 (5)
C12	0.0251 (7)	0.0259 (7)	0.0273 (7)	0.0052 (5)	−0.0003 (5)	0.0042 (5)
Cl12	0.0427 (2)	0.0438 (2)	0.02942 (19)	0.00309 (17)	0.00775 (15)	0.00411 (15)
C13	0.0239 (7)	0.0250 (7)	0.0393 (8)	−0.0008 (5)	−0.0004 (6)	0.0081 (6)
C14	0.0267 (7)	0.0198 (7)	0.0397 (8)	−0.0019 (5)	−0.0071 (6)	0.0015 (6)
C14A	0.0239 (7)	0.0198 (6)	0.0279 (7)	0.0036 (5)	−0.0063 (5)	0.0000 (5)
C14B	0.0202 (6)	0.0270 (7)	0.0259 (7)	0.0046 (5)	−0.0005 (5)	−0.0018 (5)
C15	0.0236 (7)	0.0390 (8)	0.0240 (7)	0.0046 (6)	−0.0023 (5)	−0.0047 (6)
C16	0.0266 (7)	0.0461 (9)	0.0226 (7)	0.0071 (6)	−0.0014 (5)	0.0033 (6)
C17	0.0279 (7)	0.0369 (8)	0.0308 (8)	0.0029 (6)	0.0015 (6)	0.0100 (6)
C18	0.0230 (7)	0.0296 (7)	0.0297 (7)	−0.0009 (5)	−0.0010 (5)	0.0023 (6)
C18A	0.0175 (6)	0.0275 (7)	0.0233 (6)	0.0022 (5)	−0.0009 (5)	0.0003 (5)
C18B	0.0199 (6)	0.0184 (6)	0.0263 (7)	0.0019 (5)	−0.0045 (5)	0.0017 (5)
C19	0.0225 (6)	0.0206 (6)	0.0235 (6)	0.0017 (5)	−0.0023 (5)	−0.0006 (5)
S10	0.0409 (2)	0.02266 (18)	0.02939 (19)	0.00226 (14)	−0.00557 (15)	−0.00520 (13)
C111	0.0230 (7)	0.0406 (9)	0.0384 (8)	0.0024 (6)	−0.0031 (6)	0.0023 (7)
C112	0.0449 (9)	0.0243 (7)	0.0311 (8)	−0.0040 (6)	−0.0090 (6)	0.0084 (6)
C21	0.0179 (6)	0.0223 (6)	0.0240 (6)	−0.0001 (5)	0.0026 (5)	0.0033 (5)
C22	0.0222 (6)	0.0236 (7)	0.0246 (6)	−0.0027 (5)	0.0014 (5)	0.0018 (5)
C23	0.0209 (6)	0.0296 (7)	0.0230 (7)	−0.0028 (5)	−0.0005 (5)	0.0051 (5)
C24	0.0213 (6)	0.0258 (7)	0.0304 (7)	0.0023 (5)	0.0030 (5)	0.0089 (5)
C25	0.0206 (6)	0.0212 (6)	0.0304 (7)	0.0012 (5)	0.0051 (5)	0.0015 (5)
C26	0.0196 (6)	0.0251 (7)	0.0231 (6)	−0.0007 (5)	0.0017 (5)	0.0022 (5)
C211	0.0207 (6)	0.0224 (6)	0.0236 (6)	0.0015 (5)	0.0013 (5)	0.0025 (5)
O211	0.0464 (6)	0.0297 (5)	0.0260 (5)	0.0143 (5)	−0.0089 (4)	−0.0024 (4)
O212	0.0435 (6)	0.0210 (5)	0.0344 (6)	0.0046 (4)	−0.0092 (5)	−0.0014 (4)
N23	0.0331 (7)	0.0376 (7)	0.0257 (6)	−0.0022 (5)	−0.0035 (5)	0.0070 (5)
O231	0.0792 (10)	0.0407 (7)	0.0320 (6)	−0.0072 (6)	−0.0157 (6)	−0.0005 (5)
O232	0.0626 (8)	0.0452 (7)	0.0350 (6)	0.0073 (6)	−0.0147 (6)	0.0137 (5)
N25	0.0315 (6)	0.0240 (6)	0.0391 (7)	0.0038 (5)	0.0071 (5)	−0.0005 (5)
O251	0.0621 (8)	0.0255 (6)	0.0474 (7)	0.0155 (5)	0.0130 (6)	0.0065 (5)
O252	0.0563 (8)	0.0337 (6)	0.0447 (7)	0.0083 (5)	−0.0094 (6)	−0.0113 (5)
C31	0.0211 (6)	0.0228 (6)	0.0260 (7)	0.0041 (5)	0.0055 (5)	0.0020 (5)
C32	0.0223 (6)	0.0195 (6)	0.0291 (7)	0.0040 (5)	0.0036 (5)	0.0026 (5)
C33	0.0214 (6)	0.0249 (7)	0.0289 (7)	0.0055 (5)	0.0016 (5)	−0.0004 (5)
C34	0.0234 (7)	0.0297 (7)	0.0300 (7)	0.0076 (5)	0.0024 (5)	0.0070 (6)
C35	0.0221 (7)	0.0213 (7)	0.0393 (8)	0.0048 (5)	0.0061 (6)	0.0090 (6)
C36	0.0217 (6)	0.0229 (7)	0.0323 (7)	0.0022 (5)	0.0050 (5)	0.0005 (5)
C311	0.0226 (6)	0.0269 (7)	0.0255 (7)	0.0015 (5)	0.0049 (5)	0.0011 (5)
O311	0.0533 (7)	0.0325 (6)	0.0300 (6)	−0.0053 (5)	−0.0068 (5)	−0.0006 (4)
O312	0.0335 (6)	0.0264 (5)	0.0340 (6)	−0.0007 (4)	−0.0064 (4)	0.0083 (4)
N33	0.0312 (7)	0.0320 (7)	0.0327 (7)	0.0075 (5)	−0.0026 (5)	−0.0048 (5)
O331	0.0566 (8)	0.0308 (6)	0.0460 (7)	−0.0070 (5)	−0.0067 (6)	−0.0034 (5)
O332	0.0502 (7)	0.0450 (7)	0.0351 (6)	0.0144 (6)	−0.0146 (5)	−0.0037 (5)
N35	0.0291 (7)	0.0271 (7)	0.0525 (9)	0.0005 (5)	0.0003 (6)	0.0147 (6)
O351	0.0582 (8)	0.0542 (8)	0.0540 (8)	−0.0174 (6)	−0.0167 (6)	0.0333 (7)
O352	0.0638 (9)	0.0254 (6)	0.0670 (9)	−0.0057 (6)	0.0196 (7)	0.0031 (6)

Geometric parameters (Å, º)

N1—C112	1.4874 (18)	C112—H11E	0.9800
N1—C111	1.4905 (19)	C112—H11F	0.9800
N1—C1	1.4993 (16)	C21—C22	1.3862 (19)
N1—H1	0.867 (18)	C21—C26	1.3902 (19)
C1—C2	1.5245 (19)	C21—C211	1.5167 (18)
C1—H1A	0.9900	C22—C23	1.3879 (19)
C1—H1B	0.9900	C22—H22	0.9500
C2—C3	1.5096 (18)	C23—C24	1.382 (2)
C2—H2A	0.9900	C23—N23	1.4699 (18)
C2—H2B	0.9900	C24—C25	1.382 (2)
C3—C19	1.3390 (19)	C24—H24	0.9500
C3—H4	0.9500	C25—C26	1.3842 (19)
C11—C12	1.383 (2)	C25—N25	1.4771 (18)
C11—C18B	1.3973 (19)	C26—H26	0.9500
C11—H11	0.9500	C211—O212	1.2278 (17)
C12—C13	1.390 (2)	C211—O211	1.2684 (17)
C12—Cl12	1.7317 (15)	N23—O231	1.2173 (19)
C13—C14	1.379 (2)	N23—O232	1.2226 (17)
C13—H13	0.9500	N25—O252	1.2239 (18)
C14—C14A	1.393 (2)	N25—O251	1.2254 (17)
C14—H14	0.9500	C31—C36	1.3905 (19)
C14A—C18B	1.4034 (18)	C31—C32	1.3928 (19)
C14A—S10	1.7677 (14)	C31—C311	1.5054 (19)
C14B—C15	1.3986 (19)	C32—C33	1.3846 (19)
C14B—C18A	1.4013 (19)	C32—H32	0.9500
C14B—S10	1.7685 (15)	C33—C34	1.380 (2)
C15—C16	1.382 (2)	C33—N33	1.4735 (19)
C15—H15	0.9500	C34—C35	1.381 (2)
C16—C17	1.390 (2)	C34—H34	0.9500
C16—H16	0.9500	C35—C36	1.384 (2)
C17—C18	1.387 (2)	C35—N35	1.4697 (18)
C17—H17	0.9500	C36—H36	0.9500
C18—C18A	1.403 (2)	C311—O311	1.2195 (18)
C18—H18	0.9500	C311—O312	1.2968 (18)
C18A—C19	1.4901 (18)	O312—H312	1.04 (3)
C18B—C19	1.4847 (19)	N33—O331	1.2215 (18)
C111—H11A	0.9800	N33—O332	1.2249 (17)
C111—H11B	0.9800	N35—O352	1.222 (2)
C111—H11C	0.9800	N35—O351	1.2346 (19)
C112—H11D	0.9800
C112—N1—C111	110.63 (12)	H11A—C111—H11C	109.5
C112—N1—C1	112.10 (11)	H11B—C111—H11C	109.5
C111—N1—C1	110.30 (11)	N1—C112—H11D	109.5
C112—N1—H1	110.5 (11)	N1—C112—H11E	109.5
C111—N1—H1	106.9 (11)	H11D—C112—H11E	109.5
C1—N1—H1	106.2 (11)	N1—C112—H11F	109.5
N1—C1—C2	113.84 (11)	H11D—C112—H11F	109.5
N1—C1—H1A	108.8	H11E—C112—H11F	109.5
C2—C1—H1A	108.8	C22—C21—C26	119.97 (12)
N1—C1—H1B	108.8	C22—C21—C211	119.78 (12)
C2—C1—H1B	108.8	C26—C21—C211	120.22 (12)
H1A—C1—H1B	107.7	C21—C22—C23	118.38 (13)
C3—C2—C1	108.34 (11)	C21—C22—H22	120.8
C3—C2—H2A	110.0	C23—C22—H22	120.8
C1—C2—H2A	110.0	C24—C23—C22	123.46 (13)
C3—C2—H2B	110.0	C24—C23—N23	118.42 (12)
C1—C2—H2B	110.0	C22—C23—N23	118.12 (13)
H2A—C2—H2B	108.4	C23—C24—C25	116.29 (12)
C19—C3—C2	127.90 (13)	C23—C24—H24	121.9
C19—C3—H4	116.1	C25—C24—H24	121.9
C2—C3—H4	116.1	C24—C25—C26	122.59 (13)
C12—C11—C18B	120.02 (13)	C24—C25—N25	118.95 (12)
C12—C11—H11	120.0	C26—C25—N25	118.45 (12)
C18B—C11—H11	120.0	C25—C26—C21	119.30 (12)
C11—C12—C13	121.47 (13)	C25—C26—H26	120.3
C11—C12—Cl12	119.77 (11)	C21—C26—H26	120.3
C13—C12—Cl12	118.76 (11)	O212—C211—O211	127.43 (13)
C14—C13—C12	118.81 (13)	O212—C211—C21	118.79 (12)
C14—C13—H13	120.6	O211—C211—C21	113.76 (12)
C12—C13—H13	120.6	C211—O211—H312	122.5 (12)
C13—C14—C14A	120.66 (13)	O231—N23—O232	123.75 (13)
C13—C14—H14	119.7	O231—N23—C23	118.57 (12)
C14A—C14—H14	119.7	O232—N23—C23	117.68 (13)
C14—C14A—C18B	120.45 (13)	O252—N25—O251	124.41 (13)
C14—C14A—S10	118.85 (11)	O252—N25—C25	117.92 (12)
C18B—C14A—S10	120.70 (11)	O251—N25—C25	117.67 (13)
C15—C14B—C18A	120.96 (13)	C36—C31—C32	120.02 (13)
C15—C14B—S10	118.13 (11)	C36—C31—C311	118.77 (13)
C18A—C14B—S10	120.87 (10)	C32—C31—C311	120.98 (12)
C16—C15—C14B	119.83 (14)	C33—C32—C31	118.92 (13)
C16—C15—H15	120.1	C33—C32—H32	120.5
C14B—C15—H15	120.1	C31—C32—H32	120.5
C15—C16—C17	120.05 (13)	C34—C33—C32	122.73 (13)
C15—C16—H16	120.0	C34—C33—N33	118.31 (13)
C17—C16—H16	120.0	C32—C33—N33	118.93 (13)
C18—C17—C16	120.18 (14)	C33—C34—C35	116.57 (13)
C18—C17—H17	119.9	C33—C34—H34	121.7
C16—C17—H17	119.9	C35—C34—H34	121.7
C17—C18—C18A	120.97 (14)	C34—C35—C36	123.23 (13)
C17—C18—H18	119.5	C34—C35—N35	117.87 (13)
C18A—C18—H18	119.5	C36—C35—N35	118.76 (14)
C14B—C18A—C18	117.97 (12)	C35—C36—C31	118.44 (13)
C14B—C18A—C19	119.87 (12)	C35—C36—H36	120.8
C18—C18A—C19	122.16 (12)	C31—C36—H36	120.8
C11—C18B—C14A	118.49 (13)	O311—C311—O312	125.60 (13)
C11—C18B—C19	121.32 (12)	O311—C311—C31	121.09 (13)
C14A—C18B—C19	120.08 (12)	O312—C311—C31	113.22 (12)
C3—C19—C18B	124.38 (12)	C311—O312—H312	113.3 (17)
C3—C19—C18A	120.64 (12)	O331—N33—O332	124.32 (14)
C18B—C19—C18A	114.98 (11)	O331—N33—C33	117.84 (12)
C14A—S10—C14B	99.81 (6)	O332—N33—C33	117.84 (13)
N1—C111—H11A	109.5	O352—N35—O351	124.48 (14)
N1—C111—H11B	109.5	O352—N35—C35	118.25 (14)
H11A—C111—H11B	109.5	O351—N35—C35	117.21 (14)
N1—C111—H11C	109.5
C112—N1—C1—C2	69.34 (16)	C21—C22—C23—N23	178.42 (12)
C111—N1—C1—C2	−166.89 (12)	C22—C23—C24—C25	−0.3 (2)
N1—C1—C2—C3	170.47 (11)	N23—C23—C24—C25	−179.31 (12)
C1—C2—C3—C19	138.56 (15)	C23—C24—C25—C26	1.1 (2)
C18B—C11—C12—C13	0.3 (2)	C23—C24—C25—N25	−179.97 (12)
C18B—C11—C12—Cl12	−179.78 (10)	C24—C25—C26—C21	−1.0 (2)
C11—C12—C13—C14	−1.9 (2)	N25—C25—C26—C21	−179.94 (12)
Cl12—C12—C13—C14	178.18 (11)	C22—C21—C26—C25	0.08 (19)
C12—C13—C14—C14A	0.8 (2)	C211—C21—C26—C25	178.35 (12)
C13—C14—C14A—C18B	1.8 (2)	C22—C21—C211—O212	−1.10 (19)
C13—C14—C14A—S10	−178.31 (11)	C26—C21—C211—O212	−179.38 (13)
C18A—C14B—C15—C16	−1.1 (2)	C22—C21—C211—O211	177.41 (12)
S10—C14B—C15—C16	−178.89 (11)	C26—C21—C211—O211	−0.87 (18)
C14B—C15—C16—C17	−0.4 (2)	C24—C23—N23—O231	−170.63 (14)
C15—C16—C17—C18	0.9 (2)	C22—C23—N23—O231	10.3 (2)
C16—C17—C18—C18A	0.1 (2)	C24—C23—N23—O232	10.0 (2)
C15—C14B—C18A—C18	2.1 (2)	C22—C23—N23—O232	−169.06 (14)
S10—C14B—C18A—C18	179.79 (10)	C24—C25—N25—O252	176.56 (13)
C15—C14B—C18A—C19	−177.44 (12)	C26—C25—N25—O252	−4.5 (2)
S10—C14B—C18A—C19	0.28 (18)	C24—C25—N25—O251	−3.67 (19)
C17—C18—C18A—C14B	−1.6 (2)	C26—C25—N25—O251	175.28 (13)
C17—C18—C18A—C19	177.92 (13)	C36—C31—C32—C33	−2.00 (19)
C12—C11—C18B—C14A	2.32 (19)	C311—C31—C32—C33	172.38 (12)
C12—C11—C18B—C19	178.45 (12)	C31—C32—C33—C34	−0.7 (2)
C14—C14A—C18B—C11	−3.39 (19)	C31—C32—C33—N33	−178.60 (12)
S10—C14A—C18B—C11	176.76 (10)	C32—C33—C34—C35	1.9 (2)
C14—C14A—C18B—C19	−179.57 (12)	N33—C33—C34—C35	179.82 (12)
S10—C14A—C18B—C19	0.58 (17)	C33—C34—C35—C36	−0.5 (2)
C2—C3—C19—C18B	5.4 (2)	C33—C34—C35—N35	−176.22 (12)
C2—C3—C19—C18A	−173.53 (13)	C34—C35—C36—C31	−2.1 (2)
C11—C18B—C19—C3	45.7 (2)	N35—C35—C36—C31	173.65 (12)
C14A—C18B—C19—C3	−138.19 (14)	C32—C31—C36—C35	3.3 (2)
C11—C18B—C19—C18A	−135.27 (13)	C311—C31—C36—C35	−171.21 (12)
C14A—C18B—C19—C18A	40.80 (17)	C36—C31—C311—O311	−6.4 (2)
C14B—C18A—C19—C3	137.78 (14)	C32—C31—C311—O311	179.19 (13)
C18—C18A—C19—C3	−41.7 (2)	C36—C31—C311—O312	170.31 (12)
C14B—C18A—C19—C18B	−41.26 (17)	C32—C31—C311—O312	−4.14 (18)
C18—C18A—C19—C18B	139.25 (13)	C34—C33—N33—O331	−175.17 (14)
C14—C14A—S10—C14B	146.45 (11)	C32—C33—N33—O331	2.87 (19)
C18B—C14A—S10—C14B	−33.69 (12)	C34—C33—N33—O332	4.49 (19)
C15—C14B—S10—C14A	−148.97 (11)	C32—C33—N33—O332	−177.47 (13)
C18A—C14B—S10—C14A	33.25 (12)	C34—C35—N35—O352	−166.90 (14)
C26—C21—C22—C23	0.70 (19)	C36—C35—N35—O352	17.1 (2)
C211—C21—C22—C23	−177.59 (12)	C34—C35—N35—O351	15.6 (2)
C21—C22—C23—C24	−0.6 (2)	C36—C35—N35—O351	−160.41 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O212	0.866 (17)	2.046 (17)	2.7476 (16)	137.9 (15)
N1—H1···O311	0.866 (17)	2.485 (17)	2.9848 (16)	117.5 (14)
O312—H312···O211	1.04 (3)	1.41 (3)	2.4197 (15)	161 (3)
C1—H1B···O211^i	0.99	2.36	3.2621 (18)	151
C14—H14···O232^ii	0.95	2.41	3.2917 (19)	155
C18—H18···O231	0.95	2.53	3.4386 (19)	161

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