2-Amino-4,6-bis(4-chloro­phenyl­thio)­pyrimidine

Lynch, D.E.; McClenaghan, I.

doi:10.1107/S160053680001761X

2-Amino-4,6-bis(4-chlorophenylthio)pyrimidine

The structure of the title compound, C₃₂H₂₂Cl₄N₆S₄, (I), comprises two unique molecules that separately associate via a three-centre N—H

N/S interaction to form two linear one-dimensional hydrogen-bonded chains. The dihedral angles between the two phenyl rings and the pyrimidine ring for each molecule are 84.6 (1) and 87.8 (1)°, and 83.9 (1) and 80.1 (1)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680001761X/na6000sup1.cif Contains datablocks I, default
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680001761X/na6000Isup2.hkl Contains datablock I

CCDC reference: 155857

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.056
wR factor = 0.148
Data-to-parameter ratio = 17.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               7363
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         7809
         Completeness (_total/calc)             94.29%
          Alert C: < 95% complete

PLAT_420  Alert C D-H without acceptor       N(21A) -   H(22A)            ?

PLAT_420  Alert C D-H without acceptor       N(21B) -   H(22B)            ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

Comment top

NO COMMENT

Experimental top

Crystals of (I) were obtained from Spa Contract Synthesis.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

2-Amino-4,6-bis(4-chlorophenylthio)pyrimidine top

Crystal data top

C₃₂H₂₂Cl₄N₆S₄	F(000) = 1552
M_r = 760.60	D_x = 1.487 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.4777 (13) Å	Cell parameters from 12187 reflections
b = 8.6020 (3) Å	θ = 1.0–30.5°
c = 14.2055 (5) Å	µ = 0.63 mm⁻¹
β = 102.5620 (13)°	T = 150 K
V = 3396.5 (2) Å³	Prism, colourless
Z = 4	0.15 × 0.15 × 0.10 mm

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	7363 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	4286 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ϕ and ω scans	h = −36→37
Absorption correction: multi-scan SORTAV (Blessing, 1995)	k = −11→10
T_min = 0.912, T_max = 0.940	l = −18→17
20121 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0703P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
7363 reflections	Δρ_max = 0.33 e Å⁻³
432 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (6)

Crystal data top

C₃₂H₂₂Cl₄N₆S₄	V = 3396.5 (2) Å³
M_r = 760.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 28.4777 (13) Å	µ = 0.63 mm⁻¹
b = 8.6020 (3) Å	T = 150 K
c = 14.2055 (5) Å	0.15 × 0.15 × 0.10 mm
β = 102.5620 (13)°

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	7363 independent reflections
Absorption correction: multi-scan SORTAV (Blessing, 1995)	4286 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.940	R_int = 0.080
20121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.33 e Å⁻³
7363 reflections	Δρ_min = −0.39 e Å⁻³
432 parameters

Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.3912 (0.0419) x + 8.5813 (0.0009) y - 0.5311 (0.0191) z = 0.7704 (0.0146)

* -0.0018 (0.0022) C8A * 0.0025 (0.0024) C9A * -0.0004 (0.0025) C10A * -0.0026 (0.0025) C11A * 0.0033 (0.0025) C12A * -0.0011 (0.0023) C13A

Rms deviation of fitted atoms = 0.0022

26.4157 (0.0128) x - 0.5748 (0.0101) y - 7.9624 (0.0140) z = 7.1447 (0.0154)

Angle to previous plane (with approximate e.s.d.) = 84.61 (0.11)

* -0.0017 (0.0019) N1A * -0.0013 (0.0021) C2A * 0.0036 (0.0020) N3A * -0.0031 (0.0021) C4A * 0.0002 (0.0021) C5A * 0.0023 (0.0020) C6A

Rms deviation of fitted atoms = 0.0023

- 2.0118 (0.0420) x + 8.3084 (0.0032) y - 3.2374 (0.0205) z = 4.2869 (0.0157)

Angle to previous plane (with approximate e.s.d.) = 87.80 (0.11)

* 0.0010 (0.0023) C15A * 0.0009 (0.0025) C16A * -0.0040 (0.0026) C17A * 0.0052 (0.0027) C18A * -0.0032 (0.0025) C19A * 0.0001 (0.0023) C20A

Rms deviation of fitted atoms = 0.0030

6.0898 (0.0397) x + 8.3974 (0.0027) y - 1.1546 (0.0187) z = 5.4068 (0.0123)

Angle to previous plane (with approximate e.s.d.) = 20.50 (0.07)

* -0.0117 (0.0021) C8B * 0.0024 (0.0022) C9B * 0.0091 (0.0024) C10B * -0.0113 (0.0025) C11B * 0.0017 (0.0024) C12B * 0.0098 (0.0023) C13B

Rms deviation of fitted atoms = 0.0087

- 26.2289 (0.0129) x + 0.9118 (0.0099) y + 8.0422 (0.0137) z = 3.1829 (0.0112)

Angle to previous plane (with approximate e.s.d.) = 83.87 (0.10)

* -0.0036 (0.0019) N1B * 0.0057 (0.0020) C2B * -0.0006 (0.0019) N3B * -0.0061 (0.0020) C4B * 0.0076 (0.0020) C5B * -0.0030 (0.0020) C6B

Rms deviation of fitted atoms = 0.0050

10.0127 (0.0400) x + 7.9553 (0.0047) y + 0.9270 (0.0200) z = 11.5050 (0.0120)

Angle to previous plane (with approximate e.s.d.) = 80.13 (0.10)

* -0.0087 (0.0022) C15B * 0.0038 (0.0024) C16B * -0.0002 (0.0026) C17B * 0.0014 (0.0026) C18B * -0.0063 (0.0026) C19B * 0.0100 (0.0025) C20B

Rms deviation of fitted atoms = 0.0062

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.47036 (9)	0.6658 (3)	0.61528 (16)	0.0261 (6)
C2A	0.48381 (11)	0.5371 (3)	0.66914 (19)	0.0258 (7)
N21A	0.51080 (11)	0.5590 (4)	0.75831 (19)	0.0342 (7)
H21A	0.5147 (12)	0.644 (4)	0.780 (2)	0.043 (12)*
H22A	0.5146 (14)	0.483 (5)	0.793 (3)	0.062 (14)*
N3A	0.47261 (9)	0.3895 (3)	0.64203 (16)	0.0286 (6)
C4A	0.44511 (11)	0.3712 (3)	0.55295 (19)	0.0267 (7)
C5A	0.42929 (11)	0.4931 (3)	0.49126 (19)	0.0257 (7)
H5A	0.4100	0.4777	0.4284	0.032*
C6A	0.44332 (10)	0.6389 (3)	0.52701 (19)	0.0240 (7)
S7A	0.43223 (4)	0.17497 (9)	0.52689 (6)	0.0444 (3)
C8A	0.39055 (12)	0.1785 (3)	0.4140 (2)	0.0312 (8)
C9A	0.34204 (13)	0.1709 (4)	0.4101 (2)	0.0435 (9)
H9A	0.3305	0.1732	0.4680	0.054*
C10A	0.30979 (13)	0.1599 (4)	0.3222 (2)	0.0482 (10)
H10A	0.2762	0.1542	0.3191	0.060*
C11A	0.32744 (13)	0.1574 (4)	0.2393 (2)	0.0371 (8)
Cl1A	0.28745 (4)	0.13975 (14)	0.12823 (6)	0.0620 (3)
C12A	0.37537 (13)	0.1660 (4)	0.2418 (2)	0.0420 (9)
H12A	0.3867	0.1650	0.1836	0.052*
C13A	0.40742 (12)	0.1761 (4)	0.3299 (2)	0.0387 (8)
H13A	0.4410	0.1814	0.3326	0.048*
S14A	0.42727 (3)	0.81190 (9)	0.46199 (5)	0.0345 (2)
C15A	0.38524 (11)	0.7488 (3)	0.35790 (19)	0.0283 (7)
C16A	0.33700 (13)	0.7374 (4)	0.3585 (2)	0.0417 (9)
H16A	0.3263	0.7577	0.4162	0.052*
C17A	0.30409 (13)	0.6964 (4)	0.2752 (2)	0.0479 (10)
H17A	0.2709	0.6873	0.2754	0.060*
C18A	0.32027 (13)	0.6690 (4)	0.1920 (2)	0.0417 (9)
Cl2A	0.27902 (4)	0.62041 (16)	0.08715 (6)	0.0754 (4)
C19A	0.36806 (13)	0.6789 (4)	0.1905 (2)	0.0452 (9)
H19A	0.3786	0.6581	0.1328	0.057*
C20A	0.40071 (12)	0.7196 (4)	0.2736 (2)	0.0365 (8)
H20A	0.4339	0.7277	0.2730	0.046*
N1B	0.03378 (9)	1.1381 (3)	0.37647 (16)	0.0262 (6)
C2B	0.01437 (10)	1.0095 (3)	0.32893 (19)	0.0247 (7)
N21B	−0.01250 (10)	1.0303 (4)	0.23939 (18)	0.0329 (7)
H21B	−0.0137 (11)	1.117 (4)	0.215 (2)	0.024 (9)*
H22B	−0.0223 (12)	0.951 (4)	0.204 (2)	0.045 (11)*
N3B	0.01966 (9)	0.8625 (3)	0.36203 (15)	0.0252 (6)
C4B	0.04671 (11)	0.8455 (3)	0.45152 (19)	0.0244 (7)
C5B	0.06778 (10)	0.9680 (3)	0.50803 (19)	0.0246 (7)
H5B	0.0862	0.9538	0.5717	0.031*
C6B	0.06011 (10)	1.1132 (3)	0.46523 (19)	0.0236 (7)
S7B	0.05197 (3)	0.65027 (9)	0.48769 (5)	0.0347 (2)
C8B	0.09758 (11)	0.6535 (3)	0.59522 (19)	0.0270 (7)
C9B	0.08499 (12)	0.6764 (4)	0.6830 (2)	0.0341 (8)
H9B	0.0527	0.7008	0.6853	0.043*
C10B	0.11985 (12)	0.6636 (4)	0.7677 (2)	0.0394 (9)
H10B	0.1117	0.6800	0.8283	0.049*
C11B	0.16589 (12)	0.6271 (4)	0.7630 (2)	0.0393 (9)
Cl1B	0.20838 (4)	0.60209 (15)	0.87035 (6)	0.0688 (4)
C12B	0.17931 (12)	0.6070 (4)	0.6764 (2)	0.0415 (9)
H12B	0.2117	0.5837	0.6747	0.052*
C13B	0.14481 (12)	0.6214 (4)	0.5921 (2)	0.0357 (8)
H13B	0.1535	0.6092	0.5317	0.045*
S14B	0.08396 (3)	1.28593 (9)	0.52263 (5)	0.0315 (2)
C15B	0.12233 (11)	1.2177 (3)	0.63009 (19)	0.0271 (7)
C16B	0.10738 (12)	1.2281 (4)	0.7163 (2)	0.0368 (8)
H16B	0.0764	1.2684	0.7172	0.046*
C17B	0.13721 (13)	1.1802 (4)	0.8005 (2)	0.0444 (9)
H17B	0.1268	1.1859	0.8596	0.055*
C18B	0.18226 (13)	1.1239 (4)	0.7992 (2)	0.0410 (9)
Cl2B	0.21979 (4)	1.06277 (15)	0.90598 (6)	0.0721 (4)
C19B	0.19785 (13)	1.1132 (4)	0.7142 (2)	0.0472 (10)
H19B	0.2288	1.0722	0.7137	0.059*
C20B	0.16784 (12)	1.1628 (4)	0.6297 (2)	0.0404 (9)
H20B	0.1786	1.1592	0.5709	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0308 (15)	0.0210 (13)	0.0240 (12)	0.0006 (11)	0.0003 (11)	−0.0016 (11)
C2A	0.0291 (18)	0.0262 (17)	0.0202 (15)	0.0014 (14)	0.0016 (13)	−0.0011 (13)
N21A	0.046 (2)	0.0242 (17)	0.0257 (15)	−0.0005 (14)	−0.0070 (12)	−0.0054 (14)
N3A	0.0373 (17)	0.0226 (14)	0.0227 (13)	−0.0013 (12)	−0.0003 (11)	−0.0012 (11)
C4A	0.0329 (19)	0.0250 (17)	0.0200 (14)	−0.0004 (14)	0.0010 (13)	−0.0021 (13)
C5A	0.0330 (18)	0.0194 (16)	0.0212 (14)	−0.0006 (14)	−0.0021 (12)	−0.0010 (12)
C6A	0.0261 (17)	0.0224 (16)	0.0228 (15)	0.0001 (13)	0.0035 (12)	−0.0006 (13)
S7A	0.0715 (7)	0.0186 (4)	0.0304 (4)	−0.0050 (4)	−0.0165 (4)	0.0014 (3)
C8A	0.047 (2)	0.0161 (15)	0.0245 (16)	−0.0027 (14)	−0.0040 (14)	0.0004 (13)
C9A	0.052 (3)	0.049 (2)	0.0297 (18)	−0.0034 (19)	0.0093 (16)	−0.0045 (16)
C10A	0.035 (2)	0.068 (3)	0.039 (2)	−0.0052 (19)	0.0033 (16)	0.0007 (19)
C11A	0.043 (2)	0.038 (2)	0.0265 (16)	−0.0054 (17)	−0.0012 (15)	−0.0021 (15)
Cl1A	0.0496 (6)	0.0947 (9)	0.0329 (5)	−0.0096 (6)	−0.0103 (4)	−0.0044 (5)
C12A	0.039 (2)	0.061 (2)	0.0259 (17)	−0.0015 (18)	0.0059 (15)	0.0006 (17)
C13A	0.035 (2)	0.044 (2)	0.0345 (18)	−0.0056 (16)	0.0016 (15)	0.0029 (16)
S14A	0.0505 (6)	0.0179 (4)	0.0285 (4)	0.0005 (4)	−0.0057 (4)	−0.0001 (3)
C15A	0.038 (2)	0.0180 (16)	0.0250 (15)	0.0035 (14)	−0.0014 (13)	0.0007 (13)
C16A	0.045 (2)	0.050 (2)	0.0295 (17)	0.0074 (18)	0.0063 (15)	−0.0075 (16)
C17A	0.031 (2)	0.073 (3)	0.0369 (19)	−0.0007 (19)	0.0025 (16)	−0.0074 (19)
C18A	0.041 (2)	0.053 (2)	0.0270 (17)	−0.0079 (18)	−0.0033 (15)	0.0001 (16)
Cl2A	0.0587 (7)	0.1283 (11)	0.0317 (5)	−0.0276 (7)	−0.0066 (5)	−0.0079 (6)
C19A	0.049 (2)	0.059 (2)	0.0282 (17)	−0.0121 (19)	0.0084 (16)	−0.0060 (17)
C20A	0.033 (2)	0.042 (2)	0.0325 (18)	−0.0054 (16)	0.0041 (15)	−0.0023 (15)
N1B	0.0310 (15)	0.0214 (14)	0.0246 (13)	−0.0002 (11)	0.0028 (11)	0.0003 (11)
C2B	0.0274 (18)	0.0256 (17)	0.0202 (14)	0.0026 (14)	0.0031 (12)	0.0014 (13)
N21B	0.0448 (19)	0.0252 (16)	0.0234 (14)	−0.0018 (14)	−0.0043 (12)	0.0030 (14)
N3B	0.0299 (15)	0.0224 (14)	0.0216 (12)	0.0025 (11)	0.0015 (10)	0.0001 (10)
C4B	0.0296 (18)	0.0229 (16)	0.0206 (14)	0.0013 (13)	0.0048 (12)	0.0035 (12)
C5B	0.0319 (18)	0.0211 (16)	0.0185 (14)	−0.0001 (13)	0.0004 (12)	−0.0004 (12)
C6B	0.0283 (18)	0.0211 (16)	0.0213 (14)	0.0001 (13)	0.0053 (12)	0.0020 (12)
S7B	0.0512 (6)	0.0180 (4)	0.0274 (4)	−0.0013 (4)	−0.0077 (4)	0.0012 (3)
C8B	0.040 (2)	0.0146 (15)	0.0225 (15)	−0.0003 (14)	−0.0027 (13)	0.0003 (12)
C9B	0.0317 (19)	0.038 (2)	0.0323 (17)	0.0049 (15)	0.0051 (14)	0.0004 (15)
C10B	0.039 (2)	0.053 (2)	0.0256 (16)	−0.0032 (17)	0.0073 (15)	0.0017 (16)
C11B	0.035 (2)	0.048 (2)	0.0301 (17)	−0.0010 (17)	−0.0027 (15)	0.0065 (16)
Cl1B	0.0476 (7)	0.1083 (10)	0.0398 (5)	0.0003 (6)	−0.0139 (4)	0.0095 (6)
C12B	0.028 (2)	0.055 (2)	0.0405 (19)	0.0004 (17)	0.0048 (15)	−0.0015 (18)
C13B	0.042 (2)	0.036 (2)	0.0293 (17)	−0.0004 (16)	0.0073 (15)	−0.0032 (15)
S14B	0.0436 (5)	0.0179 (4)	0.0287 (4)	−0.0022 (4)	−0.0018 (3)	0.0005 (3)
C15B	0.0331 (19)	0.0221 (16)	0.0241 (15)	−0.0052 (14)	0.0023 (13)	−0.0046 (13)
C16B	0.035 (2)	0.042 (2)	0.0330 (18)	0.0018 (16)	0.0078 (15)	−0.0026 (16)
C17B	0.048 (2)	0.059 (2)	0.0257 (17)	−0.0020 (19)	0.0073 (16)	−0.0041 (17)
C18B	0.041 (2)	0.050 (2)	0.0274 (17)	−0.0030 (18)	−0.0009 (15)	0.0042 (16)
Cl2B	0.0602 (7)	0.1112 (10)	0.0360 (5)	0.0046 (7)	−0.0095 (5)	0.0163 (6)
C19B	0.040 (2)	0.067 (3)	0.0343 (19)	0.0101 (19)	0.0057 (16)	0.0028 (18)
C20B	0.043 (2)	0.053 (2)	0.0258 (16)	0.0011 (18)	0.0098 (15)	0.0016 (16)

Geometric parameters (Å, º) top

N1A—C6A	1.341 (3)	N1B—C6B	1.337 (3)
N1A—C2A	1.353 (3)	N1B—C2B	1.350 (3)
C2A—N21A	1.344 (4)	C2B—N3B	1.346 (4)
C2A—N3A	1.345 (4)	C2B—N21B	1.346 (3)
N21A—H21A	0.79 (4)	N21B—H21B	0.82 (3)
N21A—H22A	0.81 (4)	N21B—H22B	0.86 (3)
N3A—C4A	1.345 (3)	N3B—C4B	1.343 (3)
C4A—C5A	1.378 (4)	C4B—C5B	1.380 (4)
C4A—S7A	1.750 (3)	C4B—S7B	1.753 (3)
C5A—C6A	1.380 (4)	C5B—C6B	1.385 (4)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—S14A	1.758 (3)	C6B—S14B	1.759 (3)
S7A—C8A	1.776 (3)	S7B—C8B	1.777 (3)
C8A—C9A	1.372 (5)	C8B—C9B	1.385 (4)
C8A—C13A	1.382 (4)	C8B—C13B	1.383 (4)
C9A—C10A	1.383 (4)	C9B—C10B	1.387 (4)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—C11A	1.378 (4)	C10B—C11B	1.364 (5)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.360 (5)	C11B—C12B	1.375 (4)
C11A—Cl1A	1.740 (3)	C11B—Cl1B	1.742 (3)
C12A—C13A	1.382 (4)	C12B—C13B	1.379 (4)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
S14A—C15A	1.773 (3)	S14B—C15B	1.773 (3)
C15A—C16A	1.379 (4)	C15B—C20B	1.381 (4)
C15A—C20A	1.386 (4)	C15B—C16B	1.385 (4)
C16A—C17A	1.386 (4)	C16B—C17B	1.371 (4)
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—C18A	1.379 (5)	C17B—C18B	1.375 (5)
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—C19A	1.369 (5)	C18B—C19B	1.377 (4)
C18A—Cl2A	1.735 (3)	C18B—Cl2B	1.736 (3)
C19A—C20A	1.380 (4)	C19B—C20B	1.382 (4)
C19A—H19A	0.9500	C19B—H19B	0.9500
C20A—H20A	0.9500	C20B—H20B	0.9500

C6A—N1A—C2A	115.0 (2)	C6B—N1B—C2B	115.2 (2)
N21A—C2A—N3A	117.0 (3)	N3B—C2B—N21B	116.9 (3)
N21A—C2A—N1A	116.8 (3)	N3B—C2B—N1B	126.3 (2)
N3A—C2A—N1A	126.2 (2)	N21B—C2B—N1B	116.8 (3)
C2A—N21A—H21A	120 (2)	C2B—N21B—H21B	119 (2)
C2A—N21A—H22A	116 (3)	C2B—N21B—H22B	120 (2)
H21A—N21A—H22A	121 (4)	H21B—N21B—H22B	119 (3)
C4A—N3A—C2A	115.7 (2)	C4B—N3B—C2B	115.5 (2)
N3A—C4A—C5A	123.5 (3)	N3B—C4B—C5B	123.7 (3)
N3A—C4A—S7A	111.4 (2)	N3B—C4B—S7B	112.1 (2)
C5A—C4A—S7A	125.1 (2)	C5B—C4B—S7B	124.2 (2)
C4A—C5A—C6A	115.4 (2)	C4B—C5B—C6B	115.2 (2)
C4A—C5A—H5A	122.3	C4B—C5B—H5B	122.4
C6A—C5A—H5A	122.3	C6B—C5B—H5B	122.4
N1A—C6A—C5A	124.2 (3)	N1B—C6B—C5B	124.1 (3)
N1A—C6A—S14A	112.1 (2)	N1B—C6B—S14B	112.5 (2)
C5A—C6A—S14A	123.7 (2)	C5B—C6B—S14B	123.4 (2)
C4A—S7A—C8A	104.04 (13)	C4B—S7B—C8B	103.69 (13)
C9A—C8A—C13A	120.0 (3)	C9B—C8B—C13B	120.1 (3)
C9A—C8A—S7A	120.4 (2)	C9B—C8B—S7B	119.5 (3)
C13A—C8A—S7A	119.4 (3)	C13B—C8B—S7B	120.2 (2)
C8A—C9A—C10A	120.3 (3)	C8B—C9B—C10B	119.5 (3)
C8A—C9A—H9A	119.8	C8B—C9B—H9B	120.2
C10A—C9A—H9A	119.8	C10B—C9B—H9B	120.2
C11A—C10A—C9A	118.6 (3)	C11B—C10B—C9B	119.4 (3)
C11A—C10A—H10A	120.7	C11B—C10B—H10B	120.3
C9A—C10A—H10A	120.7	C9B—C10B—H10B	120.3
C12A—C11A—C10A	121.9 (3)	C10B—C11B—C12B	122.0 (3)
C12A—C11A—Cl1A	118.9 (2)	C10B—C11B—Cl1B	118.5 (3)
C10A—C11A—Cl1A	119.2 (3)	C12B—C11B—Cl1B	119.5 (3)
C11A—C12A—C13A	119.2 (3)	C11B—C12B—C13B	118.7 (3)
C11A—C12A—H12A	120.4	C11B—C12B—H12B	120.6
C13A—C12A—H12A	120.4	C13B—C12B—H12B	120.6
C12A—C13A—C8A	119.9 (3)	C12B—C13B—C8B	120.3 (3)
C12A—C13A—H13A	120.0	C12B—C13B—H13B	119.9
C8A—C13A—H13A	120.0	C8B—C13B—H13B	119.9
C6A—S14A—C15A	103.32 (13)	C6B—S14B—C15B	102.90 (13)
C16A—C15A—C20A	119.8 (3)	C20B—C15B—C16B	119.7 (3)
C16A—C15A—S14A	120.6 (2)	C20B—C15B—S14B	120.8 (2)
C20A—C15A—S14A	119.5 (3)	C16B—C15B—S14B	119.4 (2)
C15A—C16A—C17A	120.1 (3)	C17B—C16B—C15B	120.1 (3)
C15A—C16A—H16A	119.9	C17B—C16B—H16B	120.0
C17A—C16A—H16A	119.9	C15B—C16B—H16B	120.0
C18A—C17A—C16A	119.0 (3)	C16B—C17B—C18B	119.8 (3)
C18A—C17A—H17A	120.5	C16B—C17B—H17B	120.1
C16A—C17A—H17A	120.5	C18B—C17B—H17B	120.1
C19A—C18A—C17A	121.4 (3)	C19B—C18B—C17B	121.0 (3)
C19A—C18A—Cl2A	119.4 (3)	C19B—C18B—Cl2B	119.4 (3)
C17A—C18A—Cl2A	119.1 (3)	C17B—C18B—Cl2B	119.6 (3)
C18A—C19A—C20A	119.3 (3)	C18B—C19B—C20B	119.0 (3)
C18A—C19A—H19A	120.3	C18B—C19B—H19B	120.5
C20A—C19A—H19A	120.3	C20B—C19B—H19B	120.5
C19A—C20A—C15A	120.2 (3)	C15B—C20B—C19B	120.4 (3)
C19A—C20A—H20A	119.9	C15B—C20B—H20B	119.8
C15A—C20A—H20A	119.9	C19B—C20B—H20B	119.8

C6A—N1A—C2A—N21A	−179.7 (3)	C6B—N1B—C2B—N3B	−0.8 (4)
C6A—N1A—C2A—N3A	0.0 (4)	C6B—N1B—C2B—N21B	179.8 (3)
N21A—C2A—N3A—C4A	179.2 (3)	N21B—C2B—N3B—C4B	179.9 (3)
N1A—C2A—N3A—C4A	−0.5 (5)	N1B—C2B—N3B—C4B	0.6 (4)
C2A—N3A—C4A—C5A	0.7 (4)	C2B—N3B—C4B—C5B	0.7 (4)
C2A—N3A—C4A—S7A	−179.1 (2)	C2B—N3B—C4B—S7B	−179.4 (2)
N3A—C4A—C5A—C6A	−0.4 (5)	N3B—C4B—C5B—C6B	−1.4 (4)
S7A—C4A—C5A—C6A	179.3 (2)	S7B—C4B—C5B—C6B	178.7 (2)
C2A—N1A—C6A—C5A	0.3 (4)	C2B—N1B—C6B—C5B	−0.1 (4)
C2A—N1A—C6A—S14A	179.8 (2)	C2B—N1B—C6B—S14B	−179.8 (2)
C4A—C5A—C6A—N1A	−0.2 (5)	C4B—C5B—C6B—N1B	1.1 (4)
C4A—C5A—C6A—S14A	−179.6 (2)	C4B—C5B—C6B—S14B	−179.2 (2)
N3A—C4A—S7A—C8A	173.4 (2)	N3B—C4B—S7B—C8B	169.2 (2)
C5A—C4A—S7A—C8A	−6.4 (3)	C5B—C4B—S7B—C8B	−10.9 (3)
C4A—S7A—C8A—C9A	−96.5 (3)	C4B—S7B—C8B—C9B	89.3 (3)
C4A—S7A—C8A—C13A	88.8 (3)	C4B—S7B—C8B—C13B	−95.8 (3)
C13A—C8A—C9A—C10A	0.4 (5)	C13B—C8B—C9B—C10B	−1.4 (5)
S7A—C8A—C9A—C10A	−174.3 (3)	S7B—C8B—C9B—C10B	173.6 (2)
C8A—C9A—C10A—C11A	−0.2 (5)	C8B—C9B—C10B—C11B	−0.6 (5)
C9A—C10A—C11A—C12A	−0.3 (5)	C9B—C10B—C11B—C12B	2.0 (5)
C9A—C10A—C11A—Cl1A	178.8 (3)	C9B—C10B—C11B—Cl1B	−176.8 (3)
C10A—C11A—C12A—C13A	0.6 (5)	C10B—C11B—C12B—C13B	−1.3 (5)
Cl1A—C11A—C12A—C13A	−178.4 (3)	Cl1B—C11B—C12B—C13B	177.5 (3)
C11A—C12A—C13A—C8A	−0.5 (5)	C11B—C12B—C13B—C8B	−0.8 (5)
C9A—C8A—C13A—C12A	0.0 (5)	C9B—C8B—C13B—C12B	2.1 (5)
S7A—C8A—C13A—C12A	174.7 (3)	S7B—C8B—C13B—C12B	−172.8 (2)
N1A—C6A—S14A—C15A	−171.6 (2)	N1B—C6B—S14B—C15B	−173.1 (2)
C5A—C6A—S14A—C15A	7.9 (3)	C5B—C6B—S14B—C15B	7.1 (3)
C6A—S14A—C15A—C16A	87.6 (3)	C6B—S14B—C15B—C20B	80.6 (3)
C6A—S14A—C15A—C20A	−96.2 (3)	C6B—S14B—C15B—C16B	−103.1 (3)
C20A—C15A—C16A—C17A	0.2 (5)	C20B—C15B—C16B—C17B	−1.7 (5)
S14A—C15A—C16A—C17A	176.4 (3)	S14B—C15B—C16B—C17B	−178.0 (3)
C15A—C16A—C17A—C18A	−0.7 (5)	C15B—C16B—C17B—C18B	0.9 (5)
C16A—C17A—C18A—C19A	1.1 (6)	C16B—C17B—C18B—C19B	−0.6 (6)
C16A—C17A—C18A—Cl2A	−179.0 (3)	C16B—C17B—C18B—Cl2B	−179.8 (3)
C17A—C18A—C19A—C20A	−1.0 (6)	C17B—C18B—C19B—C20B	1.2 (6)
Cl2A—C18A—C19A—C20A	179.1 (3)	Cl2B—C18B—C19B—C20B	−179.7 (3)
C18A—C19A—C20A—C15A	0.5 (5)	C16B—C15B—C20B—C19B	2.3 (5)
C16A—C15A—C20A—C19A	−0.1 (5)	S14B—C15B—C20B—C19B	178.6 (3)
S14A—C15A—C20A—C19A	−176.4 (3)	C18B—C19B—C20B—C15B	−2.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N3Aⁱ	0.79 (4)	2.38 (4)	3.165 (4)	175 (3)
N21A—H21A···S7Aⁱ	0.79 (4)	2.84 (3)	3.284 (3)	118 (3)
N21B—H21B···N3Bⁱⁱ	0.82 (3)	2.37 (3)	3.187 (4)	178 (3)
N21B—H21B···S7Bⁱⁱ	0.82 (3)	2.86 (3)	3.340 (3)	120 (2)

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

Experimental details

Crystal data
Chemical formula	C₃₂H₂₂Cl₄N₆S₄
M_r	760.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	28.4777 (13), 8.6020 (3), 14.2055 (5)
β (°)	102.5620 (13)
V (Å³)	3396.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.15 × 0.15 × 0.10

Data collection
Diffractometer	Enraf Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan SORTAV (Blessing, 1995)
T_min, T_max	0.912, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	20121, 7363, 4286
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.148, 0.97
No. of reflections	7363
No. of parameters	432
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.39

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.