4-(4-Chloro-phen-yl)-1-(2-hydr-oxy-2,2-di-phenyl-acet-yl)thio-semicarbazide.

The asymmetric unit of the title compound, C(21)H(18)ClN(3)O(2)S, contains two mol-ecules in which the bond lengths and angles are almost identical. Intra-molecular N-H⋯S hydrogen bonds result in the formation of two five-membered rings. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers; these dimers are linked via inter-molecular O-H⋯S hydrogen bonds, leading to infinite corrugated layers parallel to the bc plane through R(2) (2)(16) ring motifs.

Related literature

For a related structure, see: Ergenç et al. (1992 ▶). For general background, see: Jalilian et al. (2000 ▶); John (1998 ▶); Kucukguzel et al. (2006 ▶); Shen et al. (1998 ▶); Singh et al. (2005 ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H18ClN3O2S

M = 411.89

Monoclinic,

a = 14.1039 (19) Å

b = 18.1566 (19) Å

c = 16.9108 (19) Å

β = 114.509 (10)°

V = 3940.3 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 173 (2) K

0.9 × 0.4 × 0.4 mm

Data collection

Bruker P4 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.837, T max = 0.879

20863 measured reflections

9027 independent reflections

6867 reflections with I > 2σ(I)

R int = 0.029

2 standard reflections every 98 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.102

S = 1.02

9027 reflections

532 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.91 e Å−3

Δρmin = −0.82 e Å−3

Data collection: XSCANS (Bruker, 1996 ▶); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808035964/hk2559sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035964/hk2559Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H18ClN3O2S	F000 = 1712
Mr = 411.89	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 51 reflections
a = 14.1039 (19) Å	θ = 4.9–12.6º
b = 18.1566 (19) Å	µ = 0.32 mm−1
c = 16.9108 (19) Å	T = 173 (2) K
β = 114.509 (10)º	Prism, colorless
V = 3940.3 (9) Å3	0.9 × 0.4 × 0.4 mm
Z = 8

Bruker P4 diffractometer	Rint = 0.029
Radiation source: fine-focus sealed tube	θmax = 27.5º
Monochromator: graphite	θmin = 2.2º
T = 173(2) K	h = −18→1
ω scans	k = −23→23
Absorption correction: multi-scan(SADABS; Bruker, 2005)	l = −20→21
Tmin = 0.837, Tmax = 0.879	2 standard reflections
20863 measured reflections	every 98 reflections
9027 independent reflections	intensity decay: none
6867 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0394P)2 + 1.5051P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.91 e Å−3
9027 reflections	Δρmin = −0.82 e Å−3
532 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (2)
Secondary atom site location: difference Fourier map

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	−0.35372 (4)	0.47876 (3)	0.91532 (4)	0.04719 (14)
S1	0.10518 (4)	0.53220 (3)	0.84004 (3)	0.03220 (11)
O1	0.40810 (11)	0.59866 (7)	0.86727 (8)	0.0351 (3)
H1O	0.4136	0.5983	0.8197	0.053*
O2	0.34635 (10)	0.74781 (7)	0.97416 (9)	0.0372 (3)
N1	0.26430 (12)	0.64596 (9)	0.90301 (10)	0.0316 (3)
H1N	0.2627 (16)	0.6047 (12)	0.8741 (14)	0.041 (6)*
N2	0.18196 (12)	0.65529 (9)	0.92635 (11)	0.0327 (4)
H2N	0.1839 (18)	0.6904 (13)	0.9562 (15)	0.046 (7)*
N3	0.03119 (11)	0.62184 (8)	0.93040 (10)	0.0280 (3)
H3N	0.0423 (15)	0.6629 (11)	0.9608 (13)	0.032 (5)*
C1	0.53250 (13)	0.66591 (9)	0.98982 (11)	0.0265 (4)
C2	0.59828 (14)	0.72619 (10)	1.02190 (12)	0.0322 (4)
H2	0.5820	0.7714	0.9908	0.039*
C3	0.68734 (15)	0.72099 (12)	1.09875 (13)	0.0384 (4)
H3	0.7314	0.7627	1.1202	0.046*
C4	0.71225 (16)	0.65547 (12)	1.14417 (13)	0.0428 (5)
H4A	0.7742	0.6516	1.1961	0.051*
C5	0.64697 (17)	0.59559 (12)	1.11394 (14)	0.0436 (5)
H5	0.6635	0.5507	1.1457	0.052*
C6	0.55727 (15)	0.60058 (10)	1.03742 (13)	0.0349 (4)
H6	0.5124	0.5592	1.0173	0.042*
C7	0.43300 (14)	0.67069 (9)	0.90531 (11)	0.0281 (4)
C8	0.44508 (14)	0.72594 (10)	0.84178 (11)	0.0305 (4)
C9	0.38732 (17)	0.79023 (13)	0.81501 (14)	0.0450 (5)
H9	0.3358	0.8015	0.8356	0.054*
C10	0.4044 (2)	0.83823 (15)	0.75830 (17)	0.0616 (7)
H10	0.3651	0.8824	0.7409	0.074*
C11	0.47860 (19)	0.82192 (15)	0.72685 (15)	0.0557 (6)
H11	0.4897	0.8546	0.6876	0.067*
C12	0.53596 (16)	0.75824 (13)	0.75273 (13)	0.0441 (5)
H12	0.5866	0.7469	0.7311	0.053*
C13	0.52029 (15)	0.71046 (11)	0.81031 (12)	0.0355 (4)
H13	0.5610	0.6669	0.8285	0.043*
C14	0.34396 (13)	0.69218 (10)	0.93070 (11)	0.0277 (4)
C15	0.10457 (13)	0.60501 (9)	0.90104 (11)	0.0263 (4)
C16	−0.06058 (13)	0.58394 (9)	0.92138 (11)	0.0263 (4)
C17	−0.08058 (14)	0.50973 (10)	0.90017 (11)	0.0284 (4)
H17	−0.0326	0.4809	0.8872	0.034*
C18	−0.17141 (14)	0.47832 (10)	0.89816 (11)	0.0305 (4)
H18	−0.1858	0.4279	0.8831	0.037*
C19	−0.24083 (13)	0.51957 (11)	0.91782 (12)	0.0317 (4)
C20	−0.22088 (15)	0.59270 (11)	0.94035 (14)	0.0413 (5)
H20	−0.2680	0.6209	0.9551	0.050*
C21	−0.13118 (15)	0.62458 (11)	0.94123 (14)	0.0391 (5)
H21	−0.1178	0.6752	0.9557	0.047*
Cl2	0.85383 (5)	1.00209 (4)	0.11087 (5)	0.06182 (19)
S2	0.40487 (4)	0.95519 (3)	0.18449 (3)	0.03181 (11)
O4	0.09276 (10)	0.90499 (7)	0.15471 (8)	0.0336 (3)
H4O	0.0816	0.9066	0.1998	0.050*
O5	0.13097 (10)	0.75772 (7)	0.03205 (8)	0.0342 (3)
N4	0.22880 (12)	0.85044 (9)	0.11506 (11)	0.0325 (3)
H4N	0.2363 (17)	0.8894 (12)	0.1476 (14)	0.045 (6)*
N5	0.31033 (12)	0.83735 (9)	0.09191 (11)	0.0362 (4)
H5N	0.2991 (17)	0.8017 (13)	0.0518 (14)	0.046 (6)*
N6	0.45659 (12)	0.86864 (9)	0.07879 (11)	0.0350 (4)
H6N	0.4369 (17)	0.8333 (12)	0.0391 (14)	0.043 (6)*
C22	−0.04212 (14)	0.84829 (9)	0.02956 (11)	0.0277 (4)
C23	−0.04205 (16)	0.90432 (10)	−0.02701 (12)	0.0353 (4)
H23	0.0192	0.9327	−0.0141	0.042*
C24	−0.13058 (17)	0.91890 (11)	−0.10186 (13)	0.0418 (5)
H24	−0.1298	0.9574	−0.1396	0.050*
C25	−0.22013 (16)	0.87771 (11)	−0.12200 (13)	0.0406 (5)
H25	−0.2807	0.8877	−0.1734	0.049*
C26	−0.22073 (16)	0.82195 (11)	−0.06669 (13)	0.0391 (4)
H26	−0.2819	0.7933	−0.0803	0.047*
C27	−0.13221 (14)	0.80740 (10)	0.00893 (12)	0.0319 (4)
H27	−0.1336	0.7691	0.0467	0.038*
C28	0.05769 (14)	0.83534 (9)	0.11184 (11)	0.0272 (4)
C29	0.04543 (14)	0.77964 (10)	0.17447 (11)	0.0306 (4)
C30	0.10095 (18)	0.71399 (13)	0.19657 (15)	0.0487 (5)
H30	0.1475	0.7019	0.1709	0.058*
C31	0.0892 (2)	0.66601 (15)	0.25556 (18)	0.0653 (7)
H31	0.1275	0.6213	0.2700	0.078*
C32	0.0225 (2)	0.68284 (15)	0.29325 (15)	0.0581 (7)
H32	0.0146	0.6497	0.3336	0.070*
C33	−0.03331 (17)	0.74784 (13)	0.27265 (13)	0.0466 (5)
H33	−0.0792	0.7596	0.2990	0.056*
C34	−0.02215 (15)	0.79620 (11)	0.21312 (12)	0.0364 (4)
H34	−0.0609	0.8408	0.1988	0.044*
C35	0.14256 (14)	0.81022 (10)	0.08231 (11)	0.0285 (4)
C36	0.39154 (14)	0.88456 (10)	0.11629 (11)	0.0293 (4)
C37	0.55058 (14)	0.90486 (10)	0.08987 (11)	0.0290 (4)
C38	0.62840 (16)	0.92071 (13)	0.17052 (13)	0.0420 (5)
H38	0.6183	0.9107	0.2216	0.050*
C39	0.72165 (16)	0.95127 (13)	0.17680 (14)	0.0473 (5)
H39	0.7754	0.9623	0.2322	0.057*
C40	0.73569 (15)	0.96547 (11)	0.10254 (13)	0.0366 (4)
C41	0.65866 (14)	0.95032 (10)	0.02156 (12)	0.0322 (4)
H41	0.6691	0.9603	−0.0294	0.039*
C42	0.56583 (14)	0.92029 (10)	0.01565 (11)	0.0298 (4)
H42	0.5119	0.9101	−0.0399	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.0334 (3)	0.0594 (3)	0.0571 (3)	−0.0161 (2)	0.0271 (2)	−0.0117 (3)
S1	0.0354 (2)	0.0322 (2)	0.0347 (2)	−0.00651 (19)	0.0203 (2)	−0.00557 (18)
O1	0.0414 (8)	0.0347 (7)	0.0386 (7)	−0.0121 (6)	0.0261 (6)	−0.0140 (6)
O2	0.0322 (7)	0.0400 (7)	0.0472 (8)	−0.0083 (6)	0.0245 (6)	−0.0162 (6)
N1	0.0269 (8)	0.0357 (9)	0.0384 (8)	−0.0060 (7)	0.0196 (7)	−0.0086 (7)
N2	0.0273 (8)	0.0342 (9)	0.0427 (9)	−0.0073 (7)	0.0206 (7)	−0.0112 (7)
N3	0.0254 (8)	0.0269 (8)	0.0341 (8)	−0.0040 (6)	0.0149 (6)	−0.0040 (6)
C1	0.0246 (8)	0.0295 (9)	0.0313 (9)	−0.0011 (7)	0.0174 (7)	−0.0044 (7)
C2	0.0311 (10)	0.0328 (9)	0.0347 (9)	−0.0040 (8)	0.0158 (8)	−0.0008 (8)
C3	0.0307 (10)	0.0471 (12)	0.0375 (10)	−0.0097 (9)	0.0143 (9)	−0.0054 (9)
C4	0.0317 (10)	0.0582 (13)	0.0359 (10)	0.0033 (10)	0.0113 (9)	0.0056 (9)
C5	0.0469 (12)	0.0416 (11)	0.0457 (12)	0.0109 (10)	0.0228 (10)	0.0114 (9)
C6	0.0383 (11)	0.0307 (9)	0.0421 (10)	−0.0011 (8)	0.0232 (9)	−0.0011 (8)
C7	0.0285 (9)	0.0286 (9)	0.0319 (9)	−0.0054 (7)	0.0173 (8)	−0.0073 (7)
C8	0.0263 (9)	0.0387 (10)	0.0259 (8)	−0.0073 (8)	0.0102 (7)	−0.0034 (7)
C9	0.0371 (11)	0.0558 (13)	0.0453 (12)	0.0071 (10)	0.0204 (10)	0.0132 (10)
C10	0.0548 (15)	0.0659 (16)	0.0648 (16)	0.0168 (13)	0.0255 (13)	0.0318 (13)
C11	0.0503 (14)	0.0730 (17)	0.0456 (13)	−0.0039 (12)	0.0216 (11)	0.0225 (12)
C12	0.0372 (11)	0.0629 (14)	0.0365 (10)	−0.0121 (10)	0.0197 (9)	−0.0011 (10)
C13	0.0334 (10)	0.0429 (11)	0.0352 (10)	−0.0065 (9)	0.0193 (8)	−0.0045 (8)
C14	0.0246 (9)	0.0323 (9)	0.0285 (9)	−0.0037 (7)	0.0133 (7)	−0.0026 (7)
C15	0.0245 (8)	0.0294 (9)	0.0245 (8)	−0.0020 (7)	0.0098 (7)	0.0023 (7)
C16	0.0234 (8)	0.0302 (9)	0.0257 (8)	−0.0016 (7)	0.0107 (7)	0.0027 (7)
C17	0.0249 (8)	0.0298 (9)	0.0310 (9)	−0.0018 (7)	0.0121 (7)	−0.0002 (7)
C18	0.0281 (9)	0.0328 (9)	0.0297 (9)	−0.0061 (7)	0.0110 (7)	−0.0015 (7)
C19	0.0235 (9)	0.0410 (10)	0.0316 (9)	−0.0059 (8)	0.0124 (7)	0.0008 (8)
C20	0.0324 (10)	0.0395 (11)	0.0607 (13)	0.0004 (9)	0.0279 (10)	−0.0055 (10)
C21	0.0349 (10)	0.0312 (10)	0.0577 (13)	−0.0028 (8)	0.0256 (10)	−0.0059 (9)
Cl2	0.0482 (3)	0.0682 (4)	0.0875 (4)	−0.0305 (3)	0.0465 (3)	−0.0349 (3)
S2	0.0382 (3)	0.0311 (2)	0.0292 (2)	−0.0051 (2)	0.01702 (19)	−0.00241 (18)
O4	0.0416 (8)	0.0312 (7)	0.0379 (7)	−0.0097 (6)	0.0262 (6)	−0.0099 (5)
O5	0.0321 (7)	0.0342 (7)	0.0421 (7)	−0.0038 (6)	0.0213 (6)	−0.0107 (6)
N4	0.0285 (8)	0.0358 (9)	0.0408 (9)	−0.0061 (7)	0.0220 (7)	−0.0108 (7)
N5	0.0286 (8)	0.0410 (9)	0.0469 (10)	−0.0097 (7)	0.0236 (8)	−0.0147 (8)
N6	0.0321 (8)	0.0409 (9)	0.0383 (9)	−0.0131 (7)	0.0209 (7)	−0.0153 (7)
C22	0.0308 (9)	0.0255 (8)	0.0333 (9)	0.0023 (7)	0.0198 (8)	−0.0028 (7)
C23	0.0417 (11)	0.0321 (10)	0.0403 (10)	−0.0023 (8)	0.0254 (9)	−0.0006 (8)
C24	0.0561 (13)	0.0348 (10)	0.0388 (11)	0.0084 (10)	0.0240 (10)	0.0056 (8)
C25	0.0405 (11)	0.0437 (11)	0.0367 (10)	0.0119 (9)	0.0151 (9)	0.0004 (9)
C26	0.0325 (10)	0.0427 (11)	0.0410 (11)	0.0001 (9)	0.0142 (9)	−0.0042 (9)
C27	0.0342 (10)	0.0309 (9)	0.0346 (9)	−0.0002 (8)	0.0181 (8)	−0.0008 (8)
C28	0.0300 (9)	0.0256 (8)	0.0320 (9)	−0.0041 (7)	0.0187 (8)	−0.0048 (7)
C29	0.0290 (9)	0.0344 (10)	0.0292 (9)	−0.0082 (8)	0.0128 (8)	−0.0026 (7)
C30	0.0503 (13)	0.0486 (13)	0.0564 (13)	0.0089 (11)	0.0312 (11)	0.0164 (10)
C31	0.0720 (18)	0.0561 (15)	0.0774 (18)	0.0105 (13)	0.0405 (15)	0.0305 (13)
C32	0.0647 (16)	0.0634 (16)	0.0495 (13)	−0.0112 (13)	0.0269 (12)	0.0180 (12)
C33	0.0462 (12)	0.0634 (15)	0.0388 (11)	−0.0239 (11)	0.0263 (10)	−0.0105 (10)
C34	0.0359 (10)	0.0413 (11)	0.0362 (10)	−0.0119 (9)	0.0191 (9)	−0.0072 (8)
C35	0.0280 (9)	0.0307 (9)	0.0305 (9)	−0.0016 (7)	0.0158 (8)	0.0004 (7)
C36	0.0277 (9)	0.0332 (9)	0.0281 (9)	−0.0036 (7)	0.0127 (7)	0.0005 (7)
C37	0.0275 (9)	0.0297 (9)	0.0328 (9)	−0.0052 (7)	0.0156 (7)	−0.0037 (7)
C38	0.0361 (11)	0.0634 (14)	0.0296 (9)	−0.0134 (10)	0.0168 (8)	−0.0048 (9)
C39	0.0356 (11)	0.0711 (15)	0.0358 (10)	−0.0169 (11)	0.0155 (9)	−0.0188 (10)
C40	0.0312 (10)	0.0364 (10)	0.0499 (11)	−0.0102 (8)	0.0246 (9)	−0.0121 (9)
C41	0.0377 (10)	0.0293 (9)	0.0376 (10)	0.0009 (8)	0.0234 (8)	0.0019 (7)
C42	0.0298 (9)	0.0333 (9)	0.0261 (8)	0.0015 (8)	0.0114 (7)	−0.0005 (7)

Cl1—C19	1.7407 (18)	Cl2—C40	1.7445 (19)
S1—C15	1.6791 (18)	S2—C36	1.6824 (19)
O1—C7	1.435 (2)	O4—C28	1.439 (2)
O1—H1O	0.8400	O4—H4O	0.8400
O2—C14	1.241 (2)	O5—C35	1.242 (2)
N1—C14	1.323 (2)	N4—C35	1.327 (2)
N1—N2	1.383 (2)	N4—N5	1.380 (2)
N1—H1N	0.89 (2)	N4—H4N	0.88 (2)
N2—C15	1.349 (2)	N5—C36	1.351 (2)
N2—H2N	0.81 (2)	N5—H5N	0.90 (2)
N3—C15	1.355 (2)	N6—C36	1.345 (2)
N3—C16	1.417 (2)	N6—C37	1.421 (2)
N3—H3N	0.88 (2)	N6—H6N	0.89 (2)
C1—C2	1.391 (2)	C22—C27	1.385 (2)
C1—C6	1.394 (3)	C22—C23	1.397 (3)
C1—C7	1.535 (2)	C22—C28	1.532 (3)
C2—C3	1.386 (3)	C23—C24	1.386 (3)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.380 (3)	C24—C25	1.383 (3)
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.379 (3)	C25—C26	1.381 (3)
C4—H4A	0.9500	C25—H25	0.9500
C5—C6	1.387 (3)	C26—C27	1.392 (3)
C5—H5	0.9500	C26—H26	0.9500
C6—H6	0.9500	C27—H27	0.9500
C7—C8	1.530 (2)	C28—C29	1.525 (2)
C7—C14	1.537 (2)	C28—C35	1.545 (2)
C8—C9	1.387 (3)	C29—C30	1.390 (3)
C8—C13	1.398 (3)	C29—C34	1.394 (3)
C9—C10	1.389 (3)	C30—C31	1.385 (3)
C9—H9	0.9500	C30—H30	0.9500
C10—C11	1.389 (3)	C31—C32	1.372 (4)
C10—H10	0.9500	C31—H31	0.9500
C11—C12	1.374 (3)	C32—C33	1.380 (3)
C11—H11	0.9500	C32—H32	0.9500
C12—C13	1.389 (3)	C33—C34	1.393 (3)
C12—H12	0.9500	C33—H33	0.9500
C13—H13	0.9500	C34—H34	0.9500
C16—C21	1.388 (2)	C37—C38	1.380 (3)
C16—C17	1.393 (2)	C37—C42	1.387 (2)
C17—C18	1.390 (2)	C38—C39	1.390 (3)
C17—H17	0.9500	C38—H38	0.9500
C18—C19	1.379 (3)	C39—C40	1.375 (3)
C18—H18	0.9500	C39—H39	0.9500
C19—C20	1.378 (3)	C40—C41	1.377 (3)
C20—C21	1.386 (3)	C41—C42	1.383 (2)
C20—H20	0.9500	C41—H41	0.9500
C21—H21	0.9500	C42—H42	0.9500
C7—O1—H1O	109.5	C28—O4—H4O	109.5
C14—N1—N2	120.78 (16)	C35—N4—N5	120.94 (16)
C14—N1—H1N	123.6 (14)	C35—N4—H4N	123.9 (15)
N2—N1—H1N	115.2 (14)	N5—N4—H4N	114.8 (15)
C15—N2—N1	119.41 (16)	C36—N5—N4	120.32 (16)
C15—N2—H2N	123.1 (17)	C36—N5—H5N	123.2 (15)
N1—N2—H2N	117.5 (17)	N4—N5—H5N	115.4 (15)
C15—N3—C16	130.79 (15)	C36—N6—C37	128.29 (16)
C15—N3—H3N	115.2 (13)	C36—N6—H6N	116.9 (14)
C16—N3—H3N	114.0 (13)	C37—N6—H6N	114.7 (14)
C2—C1—C6	118.51 (17)	C27—C22—C23	118.62 (17)
C2—C1—C7	121.52 (16)	C27—C22—C28	123.20 (16)
C6—C1—C7	119.94 (16)	C23—C22—C28	118.18 (16)
C3—C2—C1	120.69 (18)	C24—C23—C22	120.55 (18)
C3—C2—H2	119.7	C24—C23—H23	119.7
C1—C2—H2	119.7	C22—C23—H23	119.7
C4—C3—C2	120.20 (19)	C25—C24—C23	120.42 (19)
C4—C3—H3	119.9	C25—C24—H24	119.8
C2—C3—H3	119.9	C23—C24—H24	119.8
C5—C4—C3	119.79 (19)	C26—C25—C24	119.42 (19)
C5—C4—H4A	120.1	C26—C25—H25	120.3
C3—C4—H4A	120.1	C24—C25—H25	120.3
C4—C5—C6	120.30 (19)	C25—C26—C27	120.40 (19)
C4—C5—H5	119.9	C25—C26—H26	119.8
C6—C5—H5	119.9	C27—C26—H26	119.8
C5—C6—C1	120.49 (18)	C22—C27—C26	120.58 (18)
C5—C6—H6	119.8	C22—C27—H27	119.7
C1—C6—H6	119.8	C26—C27—H27	119.7
O1—C7—C8	111.13 (14)	O4—C28—C29	110.30 (14)
O1—C7—C1	108.97 (14)	O4—C28—C22	108.47 (14)
C8—C7—C1	111.45 (14)	C29—C28—C22	113.96 (14)
O1—C7—C14	106.27 (13)	O4—C28—C35	105.77 (13)
C8—C7—C14	111.82 (15)	C29—C28—C35	110.80 (14)
C1—C7—C14	106.96 (13)	C22—C28—C35	107.16 (13)
C9—C8—C13	118.70 (18)	C30—C29—C34	118.53 (18)
C9—C8—C7	124.01 (17)	C30—C29—C28	122.81 (17)
C13—C8—C7	117.28 (17)	C34—C29—C28	118.63 (17)
C8—C9—C10	120.5 (2)	C31—C30—C29	120.7 (2)
C8—C9—H9	119.8	C31—C30—H30	119.6
C10—C9—H9	119.8	C29—C30—H30	119.6
C9—C10—C11	120.3 (2)	C32—C31—C30	120.3 (2)
C9—C10—H10	119.8	C32—C31—H31	119.9
C11—C10—H10	119.8	C30—C31—H31	119.9
C12—C11—C10	119.7 (2)	C31—C32—C33	120.1 (2)
C12—C11—H11	120.2	C31—C32—H32	119.9
C10—C11—H11	120.2	C33—C32—H32	119.9
C11—C12—C13	120.3 (2)	C32—C33—C34	119.9 (2)
C11—C12—H12	119.8	C32—C33—H33	120.1
C13—C12—H12	119.8	C34—C33—H33	120.1
C12—C13—C8	120.5 (2)	C33—C34—C29	120.5 (2)
C12—C13—H13	119.7	C33—C34—H34	119.8
C8—C13—H13	119.7	C29—C34—H34	119.8
O2—C14—N1	122.43 (16)	O5—C35—N4	123.06 (16)
O2—C14—C7	123.19 (15)	O5—C35—C28	123.25 (15)
N1—C14—C7	114.37 (15)	N4—C35—C28	113.68 (15)
N2—C15—N3	111.80 (15)	N6—C36—N5	112.18 (16)
N2—C15—S1	121.19 (13)	N6—C36—S2	125.65 (14)
N3—C15—S1	127.00 (13)	N5—C36—S2	122.17 (14)
C21—C16—C17	119.19 (16)	C38—C37—C42	119.58 (17)
C21—C16—N3	115.52 (15)	C38—C37—N6	122.87 (16)
C17—C16—N3	125.15 (16)	C42—C37—N6	117.42 (16)
C18—C17—C16	119.30 (17)	C37—C38—C39	119.87 (18)
C18—C17—H17	120.3	C37—C38—H38	120.1
C16—C17—H17	120.3	C39—C38—H38	120.1
C19—C18—C17	120.72 (17)	C40—C39—C38	119.69 (18)
C19—C18—H18	119.6	C40—C39—H39	120.2
C17—C18—H18	119.6	C38—C39—H39	120.2
C20—C19—C18	120.42 (17)	C39—C40—C41	121.18 (17)
C20—C19—Cl1	119.79 (15)	C39—C40—Cl2	119.50 (16)
C18—C19—Cl1	119.79 (14)	C41—C40—Cl2	119.31 (15)
C19—C20—C21	119.10 (18)	C40—C41—C42	118.90 (17)
C19—C20—H20	120.4	C40—C41—H41	120.5
C21—C20—H20	120.4	C42—C41—H41	120.5
C20—C21—C16	121.25 (18)	C41—C42—C37	120.77 (17)
C20—C21—H21	119.4	C41—C42—H42	119.6
C16—C21—H21	119.4	C37—C42—H42	119.6
C14—N1—N2—C15	−176.39 (17)	C35—N4—N5—C36	171.09 (17)
C6—C1—C2—C3	1.0 (3)	C27—C22—C23—C24	0.4 (3)
C7—C1—C2—C3	179.43 (16)	C28—C22—C23—C24	−179.29 (16)
C1—C2—C3—C4	0.5 (3)	C22—C23—C24—C25	−0.5 (3)
C2—C3—C4—C5	−1.5 (3)	C23—C24—C25—C26	0.2 (3)
C3—C4—C5—C6	1.0 (3)	C24—C25—C26—C27	0.3 (3)
C4—C5—C6—C1	0.5 (3)	C23—C22—C27—C26	0.0 (3)
C2—C1—C6—C5	−1.5 (3)	C28—C22—C27—C26	179.73 (16)
C7—C1—C6—C5	−179.97 (17)	C25—C26—C27—C22	−0.4 (3)
C2—C1—C7—O1	153.48 (15)	C27—C22—C28—O4	−130.14 (17)
C6—C1—C7—O1	−28.1 (2)	C23—C22—C28—O4	49.6 (2)
C2—C1—C7—C8	30.5 (2)	C27—C22—C28—C29	−6.9 (2)
C6—C1—C7—C8	−151.15 (16)	C23—C22—C28—C29	172.85 (15)
C2—C1—C7—C14	−92.03 (19)	C27—C22—C28—C35	116.09 (18)
C6—C1—C7—C14	86.35 (19)	C23—C22—C28—C35	−64.21 (19)
O1—C7—C8—C9	122.7 (2)	O4—C28—C29—C30	−119.9 (2)
C1—C7—C8—C9	−115.6 (2)	C22—C28—C29—C30	117.8 (2)
C14—C7—C8—C9	4.1 (2)	C35—C28—C29—C30	−3.1 (2)
O1—C7—C8—C13	−58.3 (2)	O4—C28—C29—C34	58.3 (2)
C1—C7—C8—C13	63.5 (2)	C22—C28—C29—C34	−64.0 (2)
C14—C7—C8—C13	−176.87 (15)	C35—C28—C29—C34	175.04 (15)
C13—C8—C9—C10	−0.2 (3)	C34—C29—C30—C31	0.1 (3)
C7—C8—C9—C10	178.8 (2)	C28—C29—C30—C31	178.3 (2)
C8—C9—C10—C11	0.8 (4)	C29—C30—C31—C32	−0.1 (4)
C9—C10—C11—C12	−0.6 (4)	C30—C31—C32—C33	−0.1 (4)
C10—C11—C12—C13	−0.3 (4)	C31—C32—C33—C34	0.3 (4)
C11—C12—C13—C8	0.9 (3)	C32—C33—C34—C29	−0.4 (3)
C9—C8—C13—C12	−0.6 (3)	C30—C29—C34—C33	0.1 (3)
C7—C8—C13—C12	−179.73 (17)	C28—C29—C34—C33	−178.10 (17)
N2—N1—C14—O2	−4.2 (3)	N5—N4—C35—O5	2.4 (3)
N2—N1—C14—C7	175.22 (16)	N5—N4—C35—C28	−176.98 (16)
O1—C7—C14—O2	171.68 (16)	O4—C28—C35—O5	−169.03 (16)
C8—C7—C14—O2	−66.9 (2)	C29—C28—C35—O5	71.4 (2)
C1—C7—C14—O2	55.4 (2)	C22—C28—C35—O5	−53.4 (2)
O1—C7—C14—N1	−7.7 (2)	O4—C28—C35—N4	10.4 (2)
C8—C7—C14—N1	113.68 (17)	C29—C28—C35—N4	−109.15 (17)
C1—C7—C14—N1	−124.05 (16)	C22—C28—C35—N4	125.97 (16)
N1—N2—C15—N3	179.07 (15)	C37—N6—C36—N5	−178.74 (18)
N1—N2—C15—S1	−1.2 (2)	C37—N6—C36—S2	2.3 (3)
C16—N3—C15—N2	−178.13 (16)	N4—N5—C36—N6	−171.84 (17)
C16—N3—C15—S1	2.2 (3)	N4—N5—C36—S2	7.1 (3)
C15—N3—C16—C21	−165.17 (18)	C36—N6—C37—C38	49.5 (3)
C15—N3—C16—C17	19.2 (3)	C36—N6—C37—C42	−134.7 (2)
C21—C16—C17—C18	0.9 (3)	C42—C37—C38—C39	−0.6 (3)
N3—C16—C17—C18	176.41 (16)	N6—C37—C38—C39	175.2 (2)
C16—C17—C18—C19	−0.7 (3)	C37—C38—C39—C40	0.0 (3)
C17—C18—C19—C20	−0.4 (3)	C38—C39—C40—C41	0.3 (3)
C17—C18—C19—Cl1	−179.70 (14)	C38—C39—C40—Cl2	−178.71 (18)
C18—C19—C20—C21	1.3 (3)	C39—C40—C41—C42	0.0 (3)
Cl1—C19—C20—C21	−179.38 (16)	Cl2—C40—C41—C42	179.06 (14)
C19—C20—C21—C16	−1.1 (3)	C40—C41—C42—C37	−0.7 (3)
C17—C16—C21—C20	0.0 (3)	C38—C37—C42—C41	1.0 (3)
N3—C16—C21—C20	−175.90 (19)	N6—C37—C42—C41	−175.05 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···S2i	0.84	2.44	3.2242 (13)	156
N1—H1N···S1	0.89 (2)	2.44 (2)	2.9075 (16)	113.5 (17)
N2—H2N···O5ii	0.81 (2)	2.12 (2)	2.870 (2)	155 (2)
N3—H3N···O5ii	0.88 (2)	2.17 (2)	3.003 (2)	156.1 (18)
O4—H4O···S1iii	0.84	2.51	3.2707 (13)	151
N4—H4N···S2	0.88 (2)	2.50 (2)	2.9569 (16)	113.5 (17)
N5—H5N···O2iv	0.90 (2)	1.96 (2)	2.776 (2)	149 (2)
N6—H6N···O2iv	0.89 (2)	2.02 (2)	2.842 (2)	154 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯S2i	0.84	2.44	3.2242 (13)	156
N1—H1N⋯S1	0.89 (2)	2.44 (2)	2.9075 (16)	113.5 (17)
N2—H2N⋯O5ii	0.81 (2)	2.12 (2)	2.870 (2)	155 (2)
N3—H3N⋯O5ii	0.88 (2)	2.17 (2)	3.003 (2)	156.1 (18)
O4—H4O⋯S1iii	0.84	2.51	3.2707 (13)	151
N4—H4N⋯S2	0.88 (2)	2.50 (2)	2.9569 (16)	113.5 (17)
N5—H5N⋯O2iv	0.90 (2)	1.96 (2)	2.776 (2)	149 (2)
N6—H6N⋯O2iv	0.89 (2)	2.02 (2)	2.842 (2)	154 (2)

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