1-Benzyl­sulfanyl-2-(benzyl­sulfanyl­methyl)­propanaminium chloride

Cline, D.J.; Schnieder, J.P.; Thorpe, C.; Yap, G.P.A.

doi:10.1107/S1600536804024924

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1-Benzylsulfanyl-2-(benzylsulfanylmethyl)propanaminium chloride

D. J. Cline, J. P. Schnieder, C. Thorpe and G. P. A. Yap

The title quaternary ammonium salt, C₁₈H₂₄NS₂⁺·Cl^-, was reported several decades ago, but its structure was not determined at the time. The crystal structure displays extensive hydrogen bonding, linking cations and anions into infinite chains. There are two cations and two anions in the asymmetric unit.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024924/ya6215sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024924/ya6215Isup2.hkl Contains datablock I

CCDC reference: 255882

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
R factor = 0.048
wR factor = 0.127
Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT113_ALERT_2_A ADDSYM Suggests Possible Pseudo/New Spacegroup .       Pccn

Author Response: Although the data set can be solved in the suggested space group, the structure solution in P c c n includes 3090 data rejected, 1658 systematic absence violation, a final R1 = 0.1727 wR2 = 0.5786 and an average C-C bond precision of 0.014 Angstrom. Additionally, the data E-stat, 0.789, suggests a noncentrosymmetric space group and there are no correlation matrix elements larger than 0.5 in the reported space space group, P 21 21 2.


Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....        100 PerFit

Author Response: Please see response to suggestion of P c c n spacegroup.


Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.550
           From the CIF: _refine_ls_abs_structure_Flack_su    0.060
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.55
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.08

Author Response: No obvious twinning was observed by polarized microscopy. No remaining significant peaks in the difference map.


Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.30
           From the CIF: _reflns_number_total               8603
           Count of symmetry unique reflns         5191
           Completeness (_total/calc)            165.73%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3412
           Fraction of Friedel pairs measured     0.657
           Are heavy atom types Z>Si present          yes

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SHELXTL (Sheldrick, 2001); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-Benzylsulfanyl-2-(benzylsulfanylmethyl)propanaminium chloride top

Crystal data top

C₁₈H₂₄NS₂⁺·Cl⁻	F(000) = 1504
M_r = 353.95	D_x = 1.269 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 1007 reflections
a = 16.396 (4) Å	θ = 3.2–27.8°
b = 31.633 (8) Å	µ = 0.43 mm⁻¹
c = 7.1438 (19) Å	T = 120 K
V = 3705.1 (17) Å³	Needle, yellow
Z = 8	0.36 × 0.04 × 0.04 mm

Data collection top

Bruker SMART APEX diffractometer	8603 independent reflections
Radiation source: fine-focus sealed tube	8297 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 836.6 pixels mm^-1	θ_max = 28.3°, θ_min = 1.8°
ω scans	h = −20→21
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −40→41
T_min = 0.861, T_max = 0.983	l = −9→9
41652 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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0831P)² + 1.3761P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
8603 reflections	Δρ_max = 0.50 e Å⁻³
400 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 3633 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.55 (6)

Special details top

Experimental. Data collection is performed with four batch runs at φ = 0.00 ° (600 frames), at φ = 90.00 ° (600 frames), at φ = 180 ° (600 frames) and at φ = 270 ° (600 frames). Frame width = 0.30 \& in ω. Data is merged, corrected for decay, and treated with multi-scan absorption corrections.

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.91050 (4)	0.448773 (18)	0.52541 (9)	0.02306 (14)
Cl2	0.08552 (3)	0.440842 (18)	1.02930 (9)	0.02197 (13)
N1	0.89336 (12)	0.46171 (6)	0.0836 (3)	0.0225 (4)
H1B	0.9084	0.4884	0.0514	0.034*
H1C	0.9231	0.4428	0.0164	0.034*
H1D	0.9025	0.4577	0.2079	0.034*
N2	0.10306 (12)	0.45370 (7)	0.5858 (3)	0.0230 (4)
H2B	0.0881	0.4804	0.5538	0.034*
H2C	0.0939	0.4496	0.7102	0.034*
H2D	0.0732	0.4348	0.5186	0.034*
S1	0.88438 (4)	0.36459 (2)	−0.04757 (9)	0.02450 (14)
S2	0.64440 (4)	0.46346 (2)	0.32759 (11)	0.02734 (16)
S3	0.35138 (4)	0.45585 (2)	0.82493 (11)	0.02917 (17)
S4	0.10950 (5)	0.35472 (2)	0.47148 (9)	0.02860 (16)
C1	0.87375 (14)	0.32030 (8)	0.4552 (4)	0.0222 (5)
H1A	0.8736	0.3475	0.5115	0.027*
C2	0.84365 (16)	0.28587 (9)	0.5544 (4)	0.0270 (5)
H2A	0.8236	0.2897	0.6780	0.032*
C3	0.84272 (17)	0.24640 (9)	0.4744 (4)	0.0306 (6)
H3A	0.8215	0.2230	0.5416	0.037*
C4	0.8730 (2)	0.24100 (9)	0.2947 (4)	0.0337 (7)
H4A	0.8724	0.2137	0.2390	0.040*
C5	0.90426 (18)	0.27505 (8)	0.1954 (4)	0.0283 (6)
H5A	0.9258	0.2709	0.0733	0.034*
C6	0.90402 (15)	0.31544 (8)	0.2752 (4)	0.0199 (5)
C7	0.93728 (16)	0.35285 (8)	0.1707 (4)	0.0234 (5)
H7A	0.9955	0.3476	0.1426	0.028*
H7B	0.9343	0.3780	0.2528	0.028*
C8	0.67372 (15)	0.36401 (8)	0.5734 (3)	0.0204 (5)
H8A	0.7233	0.3624	0.5048	0.025*
C9	0.63650 (17)	0.32728 (9)	0.6322 (4)	0.0250 (5)
H9A	0.6601	0.3007	0.6032	0.030*
C10	0.56450 (17)	0.32921 (9)	0.7340 (4)	0.0300 (6)
H10A	0.5390	0.3040	0.7761	0.036*
C11	0.53010 (16)	0.36805 (10)	0.7736 (4)	0.0272 (6)
H11A	0.4806	0.3694	0.8424	0.033*
C12	0.56711 (15)	0.40491 (9)	0.7139 (4)	0.0237 (5)
H12A	0.5428	0.4314	0.7417	0.028*
C13	0.64002 (15)	0.40338 (8)	0.6128 (3)	0.0192 (5)
C14	0.68167 (15)	0.44312 (8)	0.5504 (4)	0.0249 (5)
H14A	0.7409	0.4376	0.5394	0.030*
H14B	0.6740	0.4651	0.6476	0.030*
C15	0.78168 (15)	0.37539 (8)	0.0342 (4)	0.0210 (5)
H15A	0.7448	0.3755	−0.0755	0.025*
H15B	0.7645	0.3518	0.1165	0.025*
C16	0.67683 (15)	0.42253 (8)	0.1673 (4)	0.0233 (5)
H16A	0.6541	0.3953	0.2112	0.028*
H16B	0.6525	0.4285	0.0433	0.028*
C17	0.76945 (15)	0.41703 (8)	0.1412 (4)	0.0190 (5)
H17A	0.7954	0.4143	0.2674	0.023*
C18	0.80510 (14)	0.45564 (8)	0.0428 (4)	0.0221 (5)
H18A	0.7976	0.4525	−0.0940	0.027*
H18B	0.7748	0.4811	0.0829	0.027*
C19	0.43584 (15)	0.40176 (8)	1.2149 (4)	0.0225 (5)
H19A	0.4564	0.4292	1.2411	0.027*
C20	0.47821 (16)	0.36663 (10)	1.2771 (4)	0.0293 (6)
H20A	0.5269	0.3701	1.3475	0.035*
C21	0.44989 (17)	0.32639 (10)	1.2371 (4)	0.0295 (6)
H21A	0.4794	0.3023	1.2786	0.035*
C22	0.37838 (18)	0.32148 (9)	1.1365 (4)	0.0272 (6)
H22A	0.3586	0.2939	1.1089	0.033*
C23	0.33533 (15)	0.35683 (8)	1.0756 (3)	0.0201 (5)
H23A	0.2862	0.3532	1.0069	0.024*
C24	0.36342 (15)	0.39745 (8)	1.1142 (3)	0.0188 (5)
C25	0.31687 (16)	0.43547 (8)	1.0507 (4)	0.0251 (5)
H25A	0.3224	0.4580	1.1460	0.030*
H25B	0.2583	0.4281	1.0414	0.030*
C26	0.13763 (15)	0.31087 (8)	0.9772 (4)	0.0233 (5)
H26A	0.1325	0.3376	1.0369	0.028*
C27	0.17436 (16)	0.27758 (9)	1.0724 (4)	0.0269 (6)
H27A	0.1932	0.2814	1.1970	0.032*
C28	0.18329 (18)	0.23893 (9)	0.9853 (4)	0.0291 (6)
H28A	0.2095	0.2163	1.0486	0.035*
C29	0.1538 (2)	0.23324 (9)	0.8039 (4)	0.0352 (7)
H29A	0.1595	0.2066	0.7441	0.042*
C30	0.11637 (18)	0.26619 (8)	0.7111 (4)	0.0291 (6)
H30A	0.0959	0.2619	0.5881	0.035*
C31	0.10829 (15)	0.30573 (8)	0.7961 (4)	0.0220 (5)
C32	0.06632 (15)	0.34166 (8)	0.6998 (4)	0.0240 (5)
H32A	0.0693	0.3670	0.7811	0.029*
H32B	0.0080	0.3344	0.6836	0.029*
C33	0.31999 (15)	0.41423 (9)	0.6660 (4)	0.0245 (5)
H33A	0.3441	0.4200	0.5416	0.029*
H33B	0.3432	0.3872	0.7112	0.029*
C34	0.21346 (16)	0.36724 (8)	0.5329 (4)	0.0257 (5)
H34A	0.2354	0.3436	0.6086	0.031*
H34B	0.2458	0.3685	0.4160	0.031*
C35	0.22768 (15)	0.40845 (8)	0.6414 (3)	0.0187 (5)
H35A	0.2023	0.4056	0.7681	0.022*
C36	0.19134 (15)	0.44757 (8)	0.5449 (4)	0.0241 (5)
H36A	0.2217	0.4730	0.5863	0.029*
H36B	0.1987	0.4448	0.4080	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0204 (3)	0.0199 (3)	0.0289 (3)	−0.0006 (2)	−0.0028 (2)	−0.0028 (2)
Cl2	0.0196 (3)	0.0176 (3)	0.0287 (3)	−0.0001 (2)	0.0035 (2)	−0.0018 (2)
N1	0.0193 (10)	0.0168 (10)	0.0314 (11)	−0.0022 (8)	0.0037 (9)	0.0044 (9)
N2	0.0189 (10)	0.0197 (10)	0.0303 (11)	0.0016 (8)	−0.0014 (9)	0.0032 (9)
S1	0.0349 (3)	0.0227 (3)	0.0160 (3)	−0.0001 (2)	0.0046 (3)	−0.0024 (2)
S2	0.0215 (3)	0.0225 (3)	0.0380 (4)	0.0023 (2)	0.0050 (3)	0.0065 (3)
S3	0.0223 (3)	0.0232 (3)	0.0419 (4)	−0.0007 (3)	−0.0021 (3)	0.0107 (3)
S4	0.0414 (4)	0.0253 (3)	0.0191 (3)	0.0055 (3)	−0.0088 (3)	−0.0041 (2)
C1	0.0178 (11)	0.0242 (12)	0.0247 (13)	0.0034 (9)	−0.0040 (10)	−0.0065 (10)
C2	0.0248 (13)	0.0380 (14)	0.0183 (12)	0.0035 (11)	−0.0030 (11)	0.0000 (11)
C3	0.0337 (14)	0.0296 (13)	0.0286 (15)	−0.0003 (11)	−0.0066 (12)	0.0099 (12)
C4	0.0531 (19)	0.0189 (12)	0.0290 (14)	0.0045 (12)	−0.0025 (14)	−0.0038 (11)
C5	0.0396 (15)	0.0225 (12)	0.0229 (12)	0.0072 (11)	0.0021 (12)	−0.0043 (10)
C6	0.0163 (10)	0.0210 (11)	0.0224 (12)	0.0047 (9)	−0.0024 (9)	−0.0004 (9)
C7	0.0211 (12)	0.0253 (12)	0.0238 (12)	0.0005 (10)	−0.0002 (10)	0.0003 (10)
C8	0.0180 (11)	0.0293 (13)	0.0139 (10)	0.0030 (10)	−0.0019 (9)	−0.0008 (10)
C9	0.0272 (13)	0.0288 (13)	0.0191 (12)	0.0046 (11)	−0.0061 (10)	0.0014 (10)
C10	0.0295 (14)	0.0345 (15)	0.0261 (14)	−0.0053 (11)	−0.0040 (11)	0.0126 (12)
C11	0.0187 (12)	0.0463 (16)	0.0166 (12)	0.0001 (11)	0.0014 (10)	0.0057 (11)
C12	0.0195 (12)	0.0342 (14)	0.0173 (12)	0.0043 (10)	−0.0022 (10)	−0.0044 (10)
C13	0.0159 (11)	0.0255 (12)	0.0161 (11)	0.0009 (9)	−0.0032 (9)	−0.0055 (9)
C14	0.0215 (11)	0.0267 (13)	0.0265 (13)	−0.0021 (10)	0.0015 (11)	−0.0088 (11)
C15	0.0229 (11)	0.0220 (11)	0.0180 (11)	−0.0045 (9)	−0.0035 (10)	0.0014 (10)
C16	0.0200 (11)	0.0280 (13)	0.0218 (12)	−0.0034 (10)	−0.0015 (10)	0.0033 (10)
C17	0.0192 (11)	0.0211 (12)	0.0167 (11)	−0.0011 (9)	−0.0036 (9)	0.0021 (9)
C18	0.0207 (11)	0.0182 (11)	0.0273 (13)	−0.0020 (9)	−0.0009 (10)	0.0025 (10)
C19	0.0197 (11)	0.0268 (13)	0.0211 (12)	−0.0065 (10)	−0.0016 (10)	−0.0039 (10)
C20	0.0172 (11)	0.0490 (17)	0.0216 (13)	−0.0025 (12)	−0.0018 (10)	0.0074 (12)
C21	0.0278 (13)	0.0371 (15)	0.0236 (14)	0.0062 (12)	0.0030 (11)	0.0128 (12)
C22	0.0342 (14)	0.0257 (13)	0.0216 (12)	−0.0002 (11)	0.0049 (11)	0.0039 (10)
C23	0.0200 (11)	0.0265 (12)	0.0138 (10)	−0.0051 (9)	−0.0016 (9)	−0.0005 (9)
C24	0.0177 (11)	0.0266 (12)	0.0120 (10)	−0.0012 (9)	0.0037 (9)	−0.0013 (9)
C25	0.0213 (11)	0.0244 (12)	0.0296 (14)	0.0057 (10)	−0.0004 (11)	−0.0039 (11)
C26	0.0181 (11)	0.0282 (12)	0.0237 (13)	−0.0021 (9)	0.0022 (10)	−0.0078 (10)
C27	0.0264 (13)	0.0356 (14)	0.0187 (12)	−0.0035 (11)	−0.0008 (10)	−0.0033 (11)
C28	0.0382 (14)	0.0257 (13)	0.0233 (13)	−0.0010 (11)	0.0052 (12)	0.0045 (11)
C29	0.0579 (19)	0.0206 (13)	0.0271 (14)	−0.0027 (13)	0.0045 (14)	−0.0039 (11)
C30	0.0430 (16)	0.0233 (13)	0.0209 (12)	−0.0031 (12)	−0.0049 (12)	−0.0043 (10)
C31	0.0181 (11)	0.0217 (12)	0.0262 (13)	−0.0043 (9)	0.0028 (10)	−0.0025 (10)
C32	0.0195 (12)	0.0260 (13)	0.0265 (13)	0.0001 (10)	−0.0003 (10)	−0.0069 (11)
C33	0.0208 (12)	0.0303 (13)	0.0223 (13)	0.0049 (10)	0.0036 (10)	0.0090 (11)
C34	0.0307 (13)	0.0248 (12)	0.0215 (12)	0.0097 (10)	0.0073 (11)	0.0023 (11)
C35	0.0192 (11)	0.0212 (11)	0.0157 (11)	0.0063 (9)	0.0042 (9)	0.0040 (9)
C36	0.0207 (11)	0.0245 (12)	0.0271 (13)	0.0042 (9)	0.0040 (11)	0.0055 (11)

Geometric parameters (Å, º) top

N1—C18	1.488 (3)	C15—H15B	0.9900
N1—H1B	0.9100	C16—C17	1.540 (3)
N1—H1C	0.9100	C16—H16A	0.9900
N1—H1D	0.9100	C16—H16B	0.9900
N2—C36	1.489 (3)	C17—C18	1.526 (3)
N2—H2B	0.9100	C17—H17A	1.0000
N2—H2C	0.9100	C18—H18A	0.9900
N2—H2D	0.9100	C18—H18B	0.9900
S1—C15	1.815 (3)	C19—C20	1.384 (4)
S1—C7	1.822 (3)	C19—C24	1.395 (3)
S2—C16	1.809 (3)	C19—H19A	0.9500
S2—C14	1.822 (3)	C20—C21	1.385 (4)
S3—C33	1.813 (3)	C20—H20A	0.9500
S3—C25	1.827 (3)	C21—C22	1.384 (4)
S4—C34	1.804 (3)	C21—H21A	0.9500
S4—C32	1.826 (3)	C22—C23	1.392 (4)
C1—C6	1.387 (4)	C22—H22A	0.9500
C1—C2	1.390 (4)	C23—C24	1.393 (3)
C1—H1A	0.9500	C23—H23A	0.9500
C2—C3	1.373 (4)	C24—C25	1.495 (3)
C2—H2A	0.9500	C25—H25A	0.9900
C3—C4	1.387 (4)	C25—H25B	0.9900
C3—H3A	0.9500	C26—C31	1.390 (4)
C4—C5	1.387 (4)	C26—C27	1.391 (4)
C4—H4A	0.9500	C26—H26A	0.9500
C5—C6	1.399 (3)	C27—C28	1.380 (4)
C5—H5A	0.9500	C27—H27A	0.9500
C6—C7	1.502 (3)	C28—C29	1.394 (4)
C7—H7A	0.9900	C28—H28A	0.9500
C7—H7B	0.9900	C29—C30	1.379 (4)
C8—C9	1.378 (4)	C29—H29A	0.9500
C8—C13	1.391 (3)	C30—C31	1.397 (4)
C8—H8A	0.9500	C30—H30A	0.9500
C9—C10	1.388 (4)	C31—C32	1.496 (4)
C9—H9A	0.9500	C32—H32A	0.9900
C10—C11	1.381 (4)	C32—H32B	0.9900
C10—H10A	0.9500	C33—C35	1.535 (3)
C11—C12	1.382 (4)	C33—H33A	0.9900
C11—H11A	0.9500	C33—H33B	0.9900
C12—C13	1.397 (3)	C34—C35	1.535 (4)
C12—H12A	0.9500	C34—H34A	0.9900
C13—C14	1.499 (4)	C34—H34B	0.9900
C14—H14A	0.9900	C35—C36	1.536 (3)
C14—H14B	0.9900	C35—H35A	1.0000
C15—C17	1.536 (3)	C36—H36A	0.9900
C15—H15A	0.9900	C36—H36B	0.9900

C18—N1—H1B	109.5	C15—C17—H17A	108.7
C18—N1—H1C	109.5	C16—C17—H17A	108.7
H1B—N1—H1C	109.5	N1—C18—C17	112.7 (2)
C18—N1—H1D	109.5	N1—C18—H18A	109.1
H1B—N1—H1D	109.5	C17—C18—H18A	109.1
H1C—N1—H1D	109.5	N1—C18—H18B	109.1
C36—N2—H2B	109.5	C17—C18—H18B	109.1
C36—N2—H2C	109.5	H18A—C18—H18B	107.8
H2B—N2—H2C	109.5	C20—C19—C24	121.0 (2)
C36—N2—H2D	109.5	C20—C19—H19A	119.5
H2B—N2—H2D	109.5	C24—C19—H19A	119.5
H2C—N2—H2D	109.5	C21—C20—C19	120.2 (3)
C15—S1—C7	101.81 (12)	C21—C20—H20A	119.9
C16—S2—C14	101.64 (12)	C19—C20—H20A	119.9
C33—S3—C25	102.05 (12)	C22—C21—C20	119.6 (3)
C34—S4—C32	101.47 (12)	C22—C21—H21A	120.2
C6—C1—C2	120.8 (2)	C20—C21—H21A	120.2
C6—C1—H1A	119.6	C21—C22—C23	120.1 (3)
C2—C1—H1A	119.6	C21—C22—H22A	119.9
C3—C2—C1	120.3 (3)	C23—C22—H22A	119.9
C3—C2—H2A	119.9	C22—C23—C24	120.8 (2)
C1—C2—H2A	119.9	C22—C23—H23A	119.6
C2—C3—C4	119.6 (3)	C24—C23—H23A	119.6
C2—C3—H3A	120.2	C23—C24—C19	118.3 (2)
C4—C3—H3A	120.2	C23—C24—C25	120.9 (2)
C3—C4—C5	120.6 (3)	C19—C24—C25	120.8 (2)
C3—C4—H4A	119.7	C24—C25—S3	113.18 (18)
C5—C4—H4A	119.7	C24—C25—H25A	108.9
C4—C5—C6	120.0 (3)	S3—C25—H25A	108.9
C4—C5—H5A	120.0	C24—C25—H25B	108.9
C6—C5—H5A	120.0	S3—C25—H25B	108.9
C1—C6—C5	118.7 (2)	H25A—C25—H25B	107.8
C1—C6—C7	120.3 (2)	C31—C26—C27	121.1 (2)
C5—C6—C7	121.1 (2)	C31—C26—H26A	119.4
C6—C7—S1	114.41 (18)	C27—C26—H26A	119.4
C6—C7—H7A	108.7	C28—C27—C26	119.7 (3)
S1—C7—H7A	108.7	C28—C27—H27A	120.1
C6—C7—H7B	108.7	C26—C27—H27A	120.1
S1—C7—H7B	108.7	C27—C28—C29	119.8 (3)
H7A—C7—H7B	107.6	C27—C28—H28A	120.1
C9—C8—C13	121.1 (2)	C29—C28—H28A	120.1
C9—C8—H8A	119.4	C30—C29—C28	120.2 (3)
C13—C8—H8A	119.4	C30—C29—H29A	119.9
C8—C9—C10	120.0 (3)	C28—C29—H29A	119.9
C8—C9—H9A	120.0	C29—C30—C31	120.6 (3)
C10—C9—H9A	120.0	C29—C30—H30A	119.7
C11—C10—C9	119.6 (3)	C31—C30—H30A	119.7
C11—C10—H10A	120.2	C26—C31—C30	118.5 (3)
C9—C10—H10A	120.2	C26—C31—C32	119.9 (2)
C12—C11—C10	120.5 (2)	C30—C31—C32	121.6 (2)
C12—C11—H11A	119.7	C31—C32—S4	113.85 (18)
C10—C11—H11A	119.7	C31—C32—H32A	108.8
C11—C12—C13	120.4 (3)	S4—C32—H32A	108.8
C11—C12—H12A	119.8	C31—C32—H32B	108.8
C13—C12—H12A	119.8	S4—C32—H32B	108.8
C8—C13—C12	118.4 (2)	H32A—C32—H32B	107.7
C8—C13—C14	120.6 (2)	C35—C33—S3	116.00 (18)
C12—C13—C14	121.0 (2)	C35—C33—H33A	108.3
C13—C14—S2	113.79 (18)	S3—C33—H33A	108.3
C13—C14—H14A	108.8	C35—C33—H33B	108.3
S2—C14—H14A	108.8	S3—C33—H33B	108.3
C13—C14—H14B	108.8	H33A—C33—H33B	107.4
S2—C14—H14B	108.8	C35—C34—S4	116.93 (17)
H14A—C14—H14B	107.7	C35—C34—H34A	108.1
C17—C15—S1	116.28 (17)	S4—C34—H34A	108.1
C17—C15—H15A	108.2	C35—C34—H34B	108.1
S1—C15—H15A	108.2	S4—C34—H34B	108.1
C17—C15—H15B	108.2	H34A—C34—H34B	107.3
S1—C15—H15B	108.2	C34—C35—C33	108.0 (2)
H15A—C15—H15B	107.4	C34—C35—C36	113.5 (2)
C17—C16—S2	116.57 (18)	C33—C35—C36	109.8 (2)
C17—C16—H16A	108.2	C34—C35—H35A	108.5
S2—C16—H16A	108.2	C33—C35—H35A	108.5
C17—C16—H16B	108.2	C36—C35—H35A	108.5
S2—C16—H16B	108.2	N2—C36—C35	113.2 (2)
H16A—C16—H16B	107.3	N2—C36—H36A	108.9
C18—C17—C15	114.0 (2)	C35—C36—H36A	108.9
C18—C17—C16	110.1 (2)	N2—C36—H36B	108.9
C15—C17—C16	106.6 (2)	C35—C36—H36B	108.9
C18—C17—H17A	108.7	H36A—C36—H36B	107.8

C6—C1—C2—C3	−0.6 (4)	C24—C19—C20—C21	1.2 (4)
C1—C2—C3—C4	0.9 (4)	C19—C20—C21—C22	−0.8 (4)
C2—C3—C4—C5	0.1 (4)	C20—C21—C22—C23	0.1 (4)
C3—C4—C5—C6	−1.2 (5)	C21—C22—C23—C24	0.2 (4)
C2—C1—C6—C5	−0.5 (4)	C22—C23—C24—C19	0.2 (4)
C2—C1—C6—C7	−179.3 (2)	C22—C23—C24—C25	−179.4 (2)
C4—C5—C6—C1	1.3 (4)	C20—C19—C24—C23	−0.9 (4)
C4—C5—C6—C7	−179.9 (3)	C20—C19—C24—C25	178.7 (2)
C1—C6—C7—S1	−119.9 (2)	C23—C24—C25—S3	−93.7 (3)
C5—C6—C7—S1	61.3 (3)	C19—C24—C25—S3	86.8 (3)
C15—S1—C7—C6	60.9 (2)	C33—S3—C25—C24	68.4 (2)
C13—C8—C9—C10	−0.6 (4)	C31—C26—C27—C28	1.1 (4)
C8—C9—C10—C11	0.8 (4)	C26—C27—C28—C29	−1.4 (4)
C9—C10—C11—C12	−0.5 (4)	C27—C28—C29—C30	0.5 (5)
C10—C11—C12—C13	−0.1 (4)	C28—C29—C30—C31	0.7 (5)
C9—C8—C13—C12	0.0 (4)	C27—C26—C31—C30	0.1 (4)
C9—C8—C13—C14	179.2 (2)	C27—C26—C31—C32	177.7 (2)
C11—C12—C13—C8	0.4 (4)	C29—C30—C31—C26	−1.0 (4)
C11—C12—C13—C14	−178.8 (2)	C29—C30—C31—C32	−178.7 (3)
C8—C13—C14—S2	94.9 (3)	C26—C31—C32—S4	126.3 (2)
C12—C13—C14—S2	−86.0 (3)	C30—C31—C32—S4	−56.1 (3)
C16—S2—C14—C13	−66.4 (2)	C34—S4—C32—C31	−59.1 (2)
C7—S1—C15—C17	71.4 (2)	C25—S3—C33—C35	67.4 (2)
C14—S2—C16—C17	−66.1 (2)	C32—S4—C34—C35	−70.6 (2)
S1—C15—C17—C18	49.4 (3)	S4—C34—C35—C33	−176.04 (18)
S1—C15—C17—C16	171.03 (17)	S4—C34—C35—C36	−54.1 (3)
S2—C16—C17—C18	−67.5 (3)	S3—C33—C35—C34	−169.65 (17)
S2—C16—C17—C15	168.42 (17)	S3—C33—C35—C36	66.1 (3)
C15—C17—C18—N1	−84.8 (3)	C34—C35—C36—N2	83.5 (3)
C16—C17—C18—N1	155.4 (2)	C33—C35—C36—N2	−155.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl2ⁱ	0.91	2.24	3.126 (2)	163
N1—H1C···S1	0.91	2.59	3.216 (2)	126
N1—H1C···Cl2ⁱⁱ	0.91	2.66	3.242 (2)	122
N1—H1D···Cl1	0.91	2.29	3.195 (3)	174
N2—H2B···Cl1ⁱⁱⁱ	0.91	2.25	3.123 (2)	161
N2—H2C···Cl2	0.91	2.30	3.207 (3)	174
N2—H2D···S4	0.91	2.62	3.238 (2)	126
N2—H2D···Cl1^iv	0.91	2.70	3.190 (2)	114

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

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