(E)-2-[1-(1-Benzothio-phen-3-yl)ethyl-idene]hydrazinecarbothio-amide methanol hemisolvate.

The asymmetric unit of the title compound, C(11)H(11)N(3)S(2)·0.5CH(4)O, contains four thio-semicarbazone mol-ecules and two methanol solvent mol-ecules. Each hydrazinecarbothio-amide mol-ecule adopts an E configuration with respect to the C=N double bond and is stabilized by an intra-molecular N-H⋯N hydrogen bond, resulting in an S(5) ring motif. In the crystal structure, an extensive network of N-H⋯O, N-H⋯N, O-H⋯S and N-H⋯S hydrogen bonds and weak C-H⋯O, C-H⋯N and C-H⋯S contacts together with an S⋯S [3.5958 (14) Å] and a C-H⋯π inter-action form a three-dimensional network.

Related literature

For related structures, see: de Lima et al. (2002 ▶); Işık et al. (2006 ▶). For reference structural data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al., (1995 ▶).

Experimental

Crystal data

C11H11N3S2·0.5CH4O

M = 265.38

Monoclinic,

a = 18.9438 (12) Å

b = 17.7076 (11) Å

c = 15.4145 (10) Å

β = 107.238 (3)°

V = 4938.5 (5) Å3

Z = 16

Mo Kα radiation

μ = 0.41 mm−1

T = 92 (2) K

0.31 × 0.20 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.777, T max = 0.947

65034 measured reflections

10871 independent reflections

8171 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.203

S = 1.03

10871 reflections

655 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.71 e Å−3

Δρmin = −2.31 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT (Bruker, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 ▶), ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801297X/hb2725sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801297X/hb2725Isup2.hkl

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

C11H11N3S2·0.5(CH4O)	F000 = 2224
Mr = 265.38	Dx = 1.428 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8980 reflections
a = 18.9438 (12) Å	θ = 2.3–25.6º
b = 17.7076 (11) Å	µ = 0.42 mm−1
c = 15.4145 (10) Å	T = 92 (2) K
β = 107.238 (3)º	Block, colourless
V = 4938.5 (5) Å3	0.31 × 0.20 × 0.13 mm
Z = 16

Bruker APEXII CCD area-detector diffractometer	10871 independent reflections
Radiation source: fine-focus sealed tube	8171 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.086
T = 92(2) K	θmax = 27.1º
ω scans	θmin = 1.1º
Absorption correction: multi-scan(SADABS; Bruker, 2006)	h = −24→24
Tmin = 0.777, Tmax = 0.947	k = −22→22
65034 measured reflections	l = −19→18

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)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.203	w = 1/[σ2(Fo2) + (0.1068P)2 + 8.4506P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
10871 reflections	Δρmax = 1.71 e Å−3
655 parameters	Δρmin = −2.30 e Å−3
12 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1A	0.40620 (18)	0.50684 (18)	0.8528 (2)	0.0201 (7)
C2A	0.36631 (19)	0.44650 (19)	0.8029 (2)	0.0241 (7)
H2A	0.3746	0.4300	0.7480	0.029*
C3A	0.3144 (2)	0.41176 (19)	0.8364 (2)	0.0254 (7)
H3A	0.2872	0.3700	0.8046	0.030*
C4A	0.3010 (2)	0.4368 (2)	0.9163 (3)	0.0263 (8)
H4A	0.2643	0.4125	0.9370	0.032*
C5A	0.3402 (2)	0.4960 (2)	0.9651 (3)	0.0252 (7)
H5A	0.3309	0.5124	1.0193	0.030*
C6A	0.39438 (18)	0.53217 (18)	0.9341 (2)	0.0212 (7)
S1A	0.47650 (5)	0.55720 (5)	0.82797 (6)	0.0235 (2)
C7A	0.44278 (18)	0.59319 (19)	0.9744 (2)	0.0224 (7)
H7A	0.4422	0.6176	1.0291	0.027*
C8A	0.48976 (18)	0.61239 (18)	0.9258 (2)	0.0200 (7)
C9A	0.54827 (18)	0.66957 (18)	0.9473 (2)	0.0207 (7)
C10A	0.56188 (18)	0.71682 (19)	1.0314 (2)	0.0223 (7)
H10A	0.6108	0.7051	1.0729	0.033*
H10B	0.5241	0.7058	1.0614	0.033*
H10C	0.5596	0.7704	1.0150	0.033*
N1A	0.58542 (15)	0.67430 (16)	0.8893 (2)	0.0213 (6)
N2A	0.64370 (16)	0.72396 (16)	0.9091 (2)	0.0211 (6)
H2NA	0.659 (2)	0.743 (2)	0.9613 (13)	0.025*
C11A	0.67880 (18)	0.73726 (18)	0.8465 (2)	0.0194 (7)
S2A	0.75517 (5)	0.79377 (5)	0.87472 (6)	0.02159 (19)
N3A	0.65198 (17)	0.70631 (19)	0.7655 (2)	0.0261 (6)
H3N1	0.676 (2)	0.714 (2)	0.729 (2)	0.031*
H3N2	0.6187 (17)	0.6733 (18)	0.758 (3)	0.031*
C1B	0.1144 (2)	0.9732 (2)	0.6666 (2)	0.0259 (7)
C2B	0.1682 (2)	1.0138 (2)	0.7312 (3)	0.0377 (10)
H2B	0.1676	1.0165	0.7926	0.045*
C3B	0.2225 (2)	1.0503 (2)	0.7030 (3)	0.0347 (9)
H3B	0.2594	1.0787	0.7458	0.042*
C4B	0.2239 (2)	1.0461 (2)	0.6135 (3)	0.0295 (8)
H4B	0.2614	1.0720	0.5959	0.035*
C5B	0.1714 (2)	1.0047 (2)	0.5495 (3)	0.0267 (8)
H5B	0.1730	1.0015	0.4886	0.032*
C6B	0.11558 (18)	0.96745 (18)	0.5761 (2)	0.0213 (7)
S1B	0.04048 (5)	0.92419 (5)	0.68465 (6)	0.0294 (2)
C7B	0.05600 (19)	0.92149 (19)	0.5224 (2)	0.0227 (7)
H7B	0.0484	0.9107	0.4600	0.027*
C8B	0.01121 (18)	0.89489 (18)	0.5715 (2)	0.0203 (7)
C9B	−0.05345 (18)	0.84574 (18)	0.5407 (2)	0.0217 (7)
C10B	−0.0764 (2)	0.8167 (2)	0.4454 (2)	0.0269 (8)
H10D	−0.0763	0.7614	0.4461	0.040*
H10E	−0.0417	0.8349	0.4138	0.040*
H10F	−0.1262	0.8349	0.4137	0.040*
N1B	−0.08527 (15)	0.83003 (16)	0.6022 (2)	0.0212 (6)
N2B	−0.14681 (16)	0.78420 (16)	0.5770 (2)	0.0216 (6)
H2NB	−0.166 (2)	0.768 (2)	0.5243 (13)	0.026*
C11B	−0.17783 (18)	0.76294 (19)	0.6424 (2)	0.0202 (7)
S2B	−0.25346 (5)	0.70679 (5)	0.61499 (6)	0.0227 (2)
N3B	−0.14553 (16)	0.78669 (17)	0.7263 (2)	0.0233 (6)
H3N3	−0.1059 (13)	0.811 (2)	0.735 (3)	0.028*
H3N4	−0.165 (2)	0.770 (2)	0.765 (2)	0.028*
C1C	0.3583 (2)	0.7371 (2)	0.6860 (2)	0.0258 (7)
C2C	0.4354 (2)	0.7437 (2)	0.7138 (3)	0.0297 (8)
H2C	0.4661	0.7002	0.7229	0.036*
C3C	0.4653 (2)	0.8154 (2)	0.7275 (3)	0.0323 (9)
H3C	0.5175	0.8214	0.7466	0.039*
C4C	0.4199 (2)	0.8795 (2)	0.7138 (3)	0.0351 (9)
H4C	0.4419	0.9281	0.7243	0.042*
C5C	0.3439 (2)	0.8733 (2)	0.6853 (3)	0.0351 (9)
H5C	0.3138	0.9172	0.6760	0.042*
C6C	0.3117 (2)	0.8011 (2)	0.6700 (2)	0.0266 (8)
S1C	0.30752 (5)	0.65375 (5)	0.66624 (7)	0.0281 (2)
C7C	0.2349 (2)	0.7803 (2)	0.6387 (3)	0.0287 (8)
H7C	0.1955	0.8158	0.6234	0.034*
C8C	0.2248 (2)	0.70426 (19)	0.6336 (2)	0.0244 (7)
C9C	0.1548 (2)	0.6635 (2)	0.6066 (2)	0.0258 (7)
C10C	0.0836 (2)	0.7064 (2)	0.5745 (3)	0.0319 (9)
H10G	0.0759	0.7230	0.5117	0.048*
H10H	0.0857	0.7506	0.6135	0.048*
H10I	0.0426	0.6737	0.5773	0.048*
N1C	0.16139 (17)	0.59049 (17)	0.6156 (2)	0.0297 (7)
N2C	0.09860 (18)	0.54666 (18)	0.5948 (2)	0.0346 (8)
H2NC	0.0583 (14)	0.559 (3)	0.556 (3)	0.042*
C11C	0.1060 (2)	0.4744 (2)	0.6250 (3)	0.0298 (8)
S2C	0.03402 (6)	0.41383 (6)	0.60223 (8)	0.0448 (3)
N3C	0.17357 (19)	0.45564 (18)	0.6749 (2)	0.0322 (8)
H3N5	0.2098 (18)	0.485 (2)	0.688 (3)	0.050 (15)*
H3N6	0.184 (3)	0.4118 (12)	0.696 (3)	0.051 (15)*
C1D	0.1294 (2)	0.7575 (2)	0.3394 (3)	0.0292 (8)
C2D	0.0537 (2)	0.7729 (3)	0.3080 (3)	0.0398 (10)
H2D	0.0181	0.7340	0.3021	0.048*
C3D	0.0326 (3)	0.8473 (3)	0.2858 (3)	0.0445 (11)
H3D	−0.0184	0.8593	0.2636	0.053*
C4D	0.0844 (3)	0.9040 (3)	0.2953 (3)	0.0412 (10)
H4D	0.0682	0.9543	0.2798	0.049*
C5D	0.1592 (2)	0.8893 (2)	0.3268 (3)	0.0347 (9)
H5D	0.1940	0.9291	0.3334	0.042*
C6D	0.1832 (2)	0.8146 (2)	0.3492 (2)	0.0277 (8)
S1D	0.16977 (5)	0.66977 (5)	0.37222 (7)	0.0311 (2)
C7D	0.2567 (2)	0.7850 (2)	0.3818 (2)	0.0272 (8)
H7D	0.3000	0.8149	0.3917	0.033*
C8D	0.2576 (2)	0.7092 (2)	0.3971 (2)	0.0252 (7)
C9D	0.32188 (19)	0.6605 (2)	0.4331 (2)	0.0245 (7)
C10D	0.3983 (2)	0.6910 (2)	0.4466 (3)	0.0341 (9)
H10J	0.4262	0.6885	0.5112	0.051*
H10K	0.3951	0.7436	0.4261	0.051*
H10L	0.4234	0.6608	0.4113	0.051*
N1D	0.30772 (17)	0.59253 (17)	0.4530 (2)	0.0291 (7)
N2D	0.36755 (19)	0.54664 (19)	0.4909 (3)	0.0376 (8)
H2ND	0.4088 (15)	0.560 (3)	0.486 (4)	0.060 (17)*
C11D	0.3565 (2)	0.4790 (2)	0.5254 (3)	0.0313 (8)
S2D	0.43168 (7)	0.42374 (7)	0.57328 (9)	0.0476 (3)
N3D	0.28874 (19)	0.45965 (18)	0.5210 (2)	0.0317 (7)
H3N7	0.2536 (17)	0.489 (2)	0.496 (3)	0.038*
H3N8	0.284 (3)	0.4170 (13)	0.542 (3)	0.038 (13)*
O1S	0.1306 (3)	0.4894 (3)	0.4258 (4)	0.0888 (14)
H1S	0.0944	0.5187	0.4186	0.133*
C1S	0.1058 (5)	0.4166 (4)	0.4115 (5)	0.087 (2)
H1S1	0.1150	0.3907	0.4700	0.130*
H1S2	0.1321	0.3903	0.3743	0.130*
H1S3	0.0527	0.4166	0.3799	0.130*
O2S	0.5431 (3)	0.5968 (3)	0.6341 (4)	0.0867 (12)
H2S	0.5637	0.6279	0.6084	0.130*
C2S	0.5875 (4)	0.5453 (4)	0.6686 (5)	0.0867 (12)
H2S1	0.5690	0.4972	0.6390	0.130*
H2S2	0.5925	0.5417	0.7336	0.130*
H2S3	0.6357	0.5565	0.6604	0.130*

	U11	U22	U33	U12	U13	U23
C1A	0.0172 (16)	0.0190 (15)	0.0232 (16)	0.0036 (12)	0.0044 (13)	0.0020 (13)
C2A	0.0233 (18)	0.0233 (17)	0.0233 (17)	0.0026 (13)	0.0034 (14)	0.0008 (14)
C3A	0.0215 (17)	0.0193 (16)	0.0299 (18)	0.0008 (13)	−0.0009 (14)	0.0008 (14)
C4A	0.0233 (18)	0.0225 (17)	0.0321 (19)	−0.0027 (14)	0.0066 (15)	0.0042 (14)
C5A	0.0221 (17)	0.0248 (17)	0.0305 (18)	−0.0023 (13)	0.0106 (14)	−0.0021 (14)
C6A	0.0184 (16)	0.0195 (15)	0.0250 (17)	0.0019 (13)	0.0051 (13)	0.0008 (13)
S1A	0.0239 (4)	0.0254 (4)	0.0230 (4)	−0.0015 (3)	0.0099 (3)	−0.0025 (3)
C7A	0.0177 (16)	0.0219 (16)	0.0264 (17)	−0.0003 (13)	0.0048 (13)	−0.0024 (14)
C8A	0.0181 (16)	0.0184 (15)	0.0220 (16)	0.0021 (12)	0.0036 (13)	0.0009 (13)
C9A	0.0183 (16)	0.0207 (15)	0.0246 (17)	0.0035 (13)	0.0087 (13)	0.0047 (13)
C10A	0.0161 (16)	0.0240 (16)	0.0264 (17)	−0.0022 (13)	0.0058 (13)	−0.0026 (14)
N1A	0.0154 (13)	0.0234 (14)	0.0245 (14)	−0.0005 (11)	0.0052 (11)	0.0016 (11)
N2A	0.0171 (14)	0.0252 (14)	0.0227 (14)	−0.0016 (11)	0.0084 (11)	0.0004 (12)
C11A	0.0165 (15)	0.0199 (15)	0.0217 (16)	0.0059 (12)	0.0055 (12)	0.0045 (13)
S2A	0.0189 (4)	0.0245 (4)	0.0226 (4)	−0.0021 (3)	0.0080 (3)	0.0015 (3)
N3A	0.0196 (15)	0.0372 (17)	0.0234 (15)	−0.0058 (13)	0.0094 (12)	−0.0016 (13)
C1B	0.0258 (18)	0.0249 (17)	0.0278 (18)	−0.0029 (14)	0.0094 (14)	−0.0011 (14)
C2B	0.041 (2)	0.042 (2)	0.030 (2)	−0.0145 (19)	0.0110 (18)	−0.0093 (18)
C3B	0.030 (2)	0.033 (2)	0.040 (2)	−0.0115 (16)	0.0085 (17)	−0.0105 (17)
C4B	0.0217 (18)	0.0255 (18)	0.044 (2)	−0.0058 (14)	0.0135 (16)	−0.0048 (16)
C5B	0.0233 (18)	0.0245 (17)	0.035 (2)	−0.0019 (14)	0.0126 (15)	−0.0027 (15)
C6B	0.0189 (16)	0.0187 (15)	0.0256 (17)	0.0002 (12)	0.0055 (13)	−0.0002 (13)
S1B	0.0309 (5)	0.0340 (5)	0.0245 (4)	−0.0113 (4)	0.0102 (4)	−0.0034 (4)
C7B	0.0190 (16)	0.0217 (16)	0.0270 (17)	−0.0013 (13)	0.0061 (13)	−0.0008 (14)
C8B	0.0190 (16)	0.0177 (15)	0.0236 (16)	−0.0005 (12)	0.0051 (13)	0.0003 (13)
C9B	0.0186 (16)	0.0203 (16)	0.0256 (17)	0.0032 (13)	0.0056 (13)	0.0015 (13)
C10B	0.0220 (18)	0.0335 (19)	0.0258 (18)	−0.0078 (15)	0.0080 (14)	−0.0050 (15)
N1B	0.0161 (14)	0.0225 (14)	0.0252 (14)	−0.0016 (11)	0.0068 (11)	0.0015 (11)
N2B	0.0172 (14)	0.0250 (14)	0.0227 (14)	−0.0032 (11)	0.0061 (11)	−0.0004 (12)
C11B	0.0160 (15)	0.0221 (16)	0.0228 (16)	0.0048 (12)	0.0062 (12)	0.0022 (13)
S2B	0.0205 (4)	0.0264 (4)	0.0220 (4)	−0.0052 (3)	0.0075 (3)	−0.0001 (3)
N3B	0.0171 (14)	0.0313 (16)	0.0217 (14)	−0.0048 (12)	0.0060 (11)	−0.0023 (12)
C1C	0.0257 (18)	0.0245 (17)	0.0251 (17)	−0.0020 (14)	0.0045 (14)	0.0001 (14)
C2C	0.0250 (19)	0.0319 (19)	0.0292 (19)	−0.0023 (15)	0.0036 (15)	−0.0008 (16)
C3C	0.0253 (19)	0.039 (2)	0.031 (2)	−0.0068 (16)	0.0054 (16)	0.0047 (17)
C4C	0.038 (2)	0.0288 (19)	0.036 (2)	−0.0118 (17)	0.0081 (17)	0.0033 (17)
C5C	0.038 (2)	0.0220 (18)	0.042 (2)	−0.0034 (16)	0.0062 (18)	0.0031 (16)
C6C	0.0262 (19)	0.0250 (17)	0.0275 (18)	−0.0027 (14)	0.0061 (14)	0.0033 (14)
S1C	0.0214 (4)	0.0215 (4)	0.0368 (5)	0.0010 (3)	0.0014 (4)	−0.0024 (4)
C7C	0.0283 (19)	0.0264 (18)	0.0300 (19)	−0.0002 (15)	0.0065 (15)	0.0014 (15)
C8C	0.0240 (18)	0.0226 (17)	0.0244 (17)	0.0028 (14)	0.0035 (14)	0.0041 (14)
C9C	0.0237 (18)	0.0235 (17)	0.0267 (18)	0.0004 (14)	0.0019 (14)	0.0020 (14)
C10C	0.0204 (18)	0.0278 (19)	0.041 (2)	0.0020 (14)	−0.0009 (16)	0.0064 (16)
N1C	0.0202 (15)	0.0247 (15)	0.0375 (18)	−0.0022 (12)	−0.0019 (13)	0.0025 (13)
N2C	0.0241 (17)	0.0233 (15)	0.045 (2)	−0.0010 (13)	−0.0070 (14)	0.0090 (14)
C11C	0.030 (2)	0.0226 (17)	0.0310 (19)	0.0027 (15)	0.0001 (15)	0.0013 (15)
S2C	0.0349 (6)	0.0298 (5)	0.0523 (7)	−0.0090 (4)	−0.0136 (5)	0.0164 (5)
N3C	0.0283 (17)	0.0222 (16)	0.0359 (18)	0.0032 (13)	−0.0060 (14)	0.0041 (14)
C1D	0.028 (2)	0.0323 (19)	0.0278 (18)	0.0034 (15)	0.0088 (15)	0.0008 (15)
C2D	0.027 (2)	0.054 (3)	0.040 (2)	0.0070 (19)	0.0124 (17)	0.008 (2)
C3D	0.036 (2)	0.057 (3)	0.042 (2)	0.021 (2)	0.0135 (19)	0.009 (2)
C4D	0.050 (3)	0.037 (2)	0.043 (2)	0.016 (2)	0.023 (2)	0.0097 (19)
C5D	0.043 (2)	0.0285 (19)	0.036 (2)	0.0057 (17)	0.0164 (18)	0.0034 (17)
C6D	0.030 (2)	0.0279 (18)	0.0256 (18)	0.0026 (15)	0.0094 (15)	0.0015 (15)
S1D	0.0210 (5)	0.0279 (5)	0.0415 (5)	−0.0019 (4)	0.0045 (4)	0.0037 (4)
C7D	0.0275 (19)	0.0286 (18)	0.0246 (18)	0.0000 (14)	0.0064 (14)	0.0024 (14)
C8D	0.0223 (17)	0.0237 (17)	0.0275 (18)	−0.0039 (14)	0.0041 (14)	−0.0005 (14)
C9D	0.0198 (17)	0.0278 (18)	0.0239 (17)	−0.0037 (14)	0.0033 (13)	0.0030 (14)
C10D	0.0218 (19)	0.0304 (19)	0.046 (2)	−0.0019 (15)	0.0044 (17)	0.0099 (18)
N1D	0.0234 (16)	0.0246 (15)	0.0361 (17)	0.0020 (12)	0.0038 (13)	0.0047 (13)
N2D	0.0237 (17)	0.0310 (17)	0.057 (2)	0.0019 (14)	0.0092 (16)	0.0149 (16)
C11D	0.032 (2)	0.0236 (18)	0.036 (2)	0.0032 (15)	0.0071 (16)	0.0038 (16)
S2D	0.0374 (6)	0.0426 (6)	0.0628 (8)	0.0165 (5)	0.0150 (5)	0.0240 (6)
N3D	0.0286 (18)	0.0218 (15)	0.045 (2)	0.0031 (13)	0.0112 (15)	0.0087 (14)
O1S	0.089 (4)	0.094 (4)	0.089 (3)	0.009 (3)	0.035 (3)	−0.003 (3)
C1S	0.111 (6)	0.074 (5)	0.080 (5)	−0.010 (4)	0.034 (4)	−0.018 (4)
O2S	0.099 (3)	0.064 (2)	0.097 (3)	0.013 (2)	0.030 (2)	−0.002 (2)
C2S	0.099 (3)	0.064 (2)	0.097 (3)	0.013 (2)	0.030 (2)	−0.002 (2)

C1A—C2A	1.400 (5)	C3C—H3C	0.9500
C1A—C6A	1.410 (5)	C4C—C5C	1.379 (6)
C1A—S1A	1.737 (3)	C4C—H4C	0.9500
C2A—C3A	1.384 (5)	C5C—C6C	1.406 (5)
C2A—H2A	0.9500	C5C—H5C	0.9500
C3A—C4A	1.400 (5)	C6C—C7C	1.439 (5)
C3A—H3A	0.9500	S1C—C8C	1.744 (4)
C4A—C5A	1.373 (5)	C7C—C8C	1.359 (5)
C4A—H4A	0.9500	C7C—H7C	0.9500
C5A—C6A	1.407 (5)	C8C—C9C	1.458 (5)
C5A—H5A	0.9500	C9C—N1C	1.303 (5)
C6A—C7A	1.434 (5)	C9C—C10C	1.499 (5)
S1A—C8A	1.751 (3)	C10C—H10G	0.9800
C7A—C8A	1.366 (5)	C10C—H10H	0.9800
C7A—H7A	0.9500	C10C—H10I	0.9800
C8A—C9A	1.465 (5)	N1C—N2C	1.376 (4)
C9A—N1A	1.294 (4)	N2C—C11C	1.355 (5)
C9A—C10A	1.501 (5)	N2C—H2NC	0.842 (10)
C10A—H10A	0.9800	C11C—N3C	1.326 (5)
C10A—H10B	0.9800	C11C—S2C	1.687 (4)
C10A—H10C	0.9800	N3C—H3N5	0.842 (10)
N1A—N2A	1.373 (4)	N3C—H3N6	0.840 (10)
N2A—C11A	1.346 (4)	C1D—C2D	1.396 (5)
N2A—H2NA	0.841 (10)	C1D—C6D	1.412 (5)
C11A—N3A	1.319 (4)	C1D—S1D	1.740 (4)
C11A—S2A	1.706 (3)	C2D—C3D	1.390 (6)
N3A—H3N1	0.839 (10)	C2D—H2D	0.9500
N3A—H3N2	0.843 (10)	C3D—C4D	1.382 (7)
C1B—C2B	1.395 (5)	C3D—H3D	0.9500
C1B—C6B	1.405 (5)	C4D—C5D	1.379 (6)
C1B—S1B	1.739 (4)	C4D—H4D	0.9500
C2B—C3B	1.390 (6)	C5D—C6D	1.408 (5)
C2B—H2B	0.9500	C5D—H5D	0.9500
C3B—C4B	1.390 (6)	C6D—C7D	1.432 (5)
C3B—H3B	0.9500	S1D—C8D	1.739 (4)
C4B—C5B	1.386 (5)	S1D—S1Bi	3.5958 (14)
C4B—H4B	0.9500	C7D—C8D	1.362 (5)
C5B—C6B	1.407 (5)	C7D—H7D	0.9500
C5B—H5B	0.9500	C8D—C9D	1.461 (5)
C6B—C7B	1.438 (5)	C9D—N1D	1.290 (5)
S1B—C8B	1.746 (3)	C9D—C10D	1.500 (5)
C7B—C8B	1.376 (5)	C10D—H10J	0.9800
C7B—H7B	0.9500	C10D—H10K	0.9800
C8B—C9B	1.462 (5)	C10D—H10L	0.9800
C9B—N1B	1.296 (5)	N1D—N2D	1.376 (4)
C9B—C10B	1.495 (5)	N2D—C11D	1.352 (5)
C10B—H10D	0.9800	N2D—H2ND	0.842 (10)
C10B—H10E	0.9800	C11D—N3D	1.311 (5)
C10B—H10F	0.9800	C11D—S2D	1.705 (4)
N1B—N2B	1.379 (4)	N3D—H3N7	0.841 (10)
N2B—C11B	1.362 (4)	N3D—H3N8	0.840 (10)
N2B—H2NB	0.839 (10)	O1S—C1S	1.367 (8)
C11B—N3B	1.325 (4)	O1S—H1S	0.8400
C11B—S2B	1.692 (3)	C1S—H1S1	0.9800
N3B—H3N3	0.838 (10)	C1S—H1S2	0.9800
N3B—H3N4	0.839 (10)	C1S—H1S3	0.9800
C1C—C2C	1.399 (5)	O2S—C2S	1.248 (8)
C1C—C6C	1.413 (5)	O2S—H2S	0.8400
C1C—S1C	1.738 (4)	C2S—H2S1	0.9800
C2C—C3C	1.381 (5)	C2S—H2S2	0.9800
C2C—H2C	0.9500	C2S—H2S3	0.9800
C3C—C4C	1.401 (6)
C2A—C1A—C6A	121.9 (3)	C4C—C3C—H3C	119.5
C2A—C1A—S1A	126.5 (3)	C5C—C4C—C3C	121.3 (4)
C6A—C1A—S1A	111.5 (2)	C5C—C4C—H4C	119.3
C3A—C2A—C1A	117.5 (3)	C3C—C4C—H4C	119.3
C3A—C2A—H2A	121.3	C4C—C5C—C6C	119.0 (4)
C1A—C2A—H2A	121.3	C4C—C5C—H5C	120.5
C2A—C3A—C4A	121.4 (3)	C6C—C5C—H5C	120.5
C2A—C3A—H3A	119.3	C5C—C6C—C1C	118.9 (3)
C4A—C3A—H3A	119.3	C5C—C6C—C7C	129.4 (4)
C5A—C4A—C3A	120.9 (3)	C1C—C6C—C7C	111.7 (3)
C5A—C4A—H4A	119.5	C1C—S1C—C8C	91.05 (17)
C3A—C4A—H4A	119.5	C8C—C7C—C6C	112.6 (3)
C4A—C5A—C6A	119.5 (3)	C8C—C7C—H7C	123.7
C4A—C5A—H5A	120.3	C6C—C7C—H7C	123.7
C6A—C5A—H5A	120.3	C7C—C8C—C9C	127.4 (3)
C5A—C6A—C1A	118.7 (3)	C7C—C8C—S1C	113.1 (3)
C5A—C6A—C7A	129.2 (3)	C9C—C8C—S1C	119.5 (3)
C1A—C6A—C7A	112.1 (3)	N1C—C9C—C8C	114.2 (3)
C1A—S1A—C8A	91.19 (16)	N1C—C9C—C10C	125.9 (3)
C8A—C7A—C6A	112.7 (3)	C8C—C9C—C10C	119.8 (3)
C8A—C7A—H7A	123.6	C9C—C10C—H10G	109.5
C6A—C7A—H7A	123.6	C9C—C10C—H10H	109.5
C7A—C8A—C9A	128.3 (3)	H10G—C10C—H10H	109.5
C7A—C8A—S1A	112.5 (3)	C9C—C10C—H10I	109.5
C9A—C8A—S1A	119.1 (3)	H10G—C10C—H10I	109.5
N1A—C9A—C8A	114.7 (3)	H10H—C10C—H10I	109.5
N1A—C9A—C10A	124.9 (3)	C9C—N1C—N2C	119.1 (3)
C8A—C9A—C10A	120.4 (3)	C11C—N2C—N1C	117.3 (3)
C9A—C10A—H10A	109.5	C11C—N2C—H2NC	117 (3)
C9A—C10A—H10B	109.5	N1C—N2C—H2NC	124 (3)
H10A—C10A—H10B	109.5	N3C—C11C—N2C	114.8 (3)
C9A—C10A—H10C	109.5	N3C—C11C—S2C	122.9 (3)
H10A—C10A—H10C	109.5	N2C—C11C—S2C	122.3 (3)
H10B—C10A—H10C	109.5	C11C—N3C—H3N5	124 (4)
C9A—N1A—N2A	117.0 (3)	C11C—N3C—H3N6	122 (4)
C11A—N2A—N1A	119.2 (3)	H3N5—N3C—H3N6	114 (5)
C11A—N2A—H2NA	120 (3)	C2D—C1D—C6D	122.1 (4)
N1A—N2A—H2NA	120 (3)	C2D—C1D—S1D	126.4 (3)
N3A—C11A—N2A	118.2 (3)	C6D—C1D—S1D	111.5 (3)
N3A—C11A—S2A	123.0 (3)	C3D—C2D—C1D	117.4 (4)
N2A—C11A—S2A	118.8 (3)	C3D—C2D—H2D	121.3
C11A—N3A—H3N1	116 (3)	C1D—C2D—H2D	121.3
C11A—N3A—H3N2	119 (3)	C4D—C3D—C2D	121.3 (4)
H3N1—N3A—H3N2	124 (4)	C4D—C3D—H3D	119.3
C2B—C1B—C6B	121.5 (3)	C2D—C3D—H3D	119.3
C2B—C1B—S1B	126.5 (3)	C5D—C4D—C3D	121.5 (4)
C6B—C1B—S1B	111.9 (3)	C5D—C4D—H4D	119.2
C3B—C2B—C1B	117.9 (4)	C3D—C4D—H4D	119.2
C3B—C2B—H2B	121.0	C4D—C5D—C6D	119.2 (4)
C1B—C2B—H2B	121.0	C4D—C5D—H5D	120.4
C2B—C3B—C4B	121.3 (4)	C6D—C5D—H5D	120.4
C2B—C3B—H3B	119.4	C5D—C6D—C1D	118.4 (4)
C4B—C3B—H3B	119.4	C5D—C6D—C7D	129.8 (4)
C5B—C4B—C3B	120.9 (4)	C1D—C6D—C7D	111.8 (3)
C5B—C4B—H4B	119.5	C8D—S1D—C1D	90.87 (18)
C3B—C4B—H4B	119.5	C8D—S1D—S1Bi	137.93 (13)
C4B—C5B—C6B	118.9 (4)	C1D—S1D—S1Bi	92.50 (13)
C4B—C5B—H5B	120.5	C8D—C7D—C6D	112.5 (3)
C6B—C5B—H5B	120.5	C8D—C7D—H7D	123.8
C1B—C6B—C5B	119.3 (3)	C6D—C7D—H7D	123.8
C1B—C6B—C7B	111.8 (3)	C7D—C8D—C9D	127.8 (3)
C5B—C6B—C7B	128.9 (3)	C7D—C8D—S1D	113.3 (3)
C1B—S1B—C8B	91.17 (17)	C9D—C8D—S1D	118.8 (3)
C8B—C7B—C6B	112.6 (3)	N1D—C9D—C8D	115.6 (3)
C8B—C7B—H7B	123.7	N1D—C9D—C10D	124.3 (3)
C6B—C7B—H7B	123.7	C8D—C9D—C10D	120.1 (3)
C7B—C8B—C9B	128.3 (3)	C9D—C10D—H10J	109.5
C7B—C8B—S1B	112.5 (3)	C9D—C10D—H10K	109.5
C9B—C8B—S1B	119.2 (3)	H10J—C10D—H10K	109.5
N1B—C9B—C8B	114.7 (3)	C9D—C10D—H10L	109.5
N1B—C9B—C10B	125.7 (3)	H10J—C10D—H10L	109.5
C8B—C9B—C10B	119.7 (3)	H10K—C10D—H10L	109.5
C9B—C10B—H10D	109.5	C9D—N1D—N2D	116.7 (3)
C9B—C10B—H10E	109.5	C11D—N2D—N1D	119.1 (3)
H10D—C10B—H10E	109.5	C11D—N2D—H2ND	123 (4)
C9B—C10B—H10F	109.5	N1D—N2D—H2ND	117 (4)
H10D—C10B—H10F	109.5	N3D—C11D—N2D	118.3 (3)
H10E—C10B—H10F	109.5	N3D—C11D—S2D	123.5 (3)
C9B—N1B—N2B	117.2 (3)	N2D—C11D—S2D	118.2 (3)
C11B—N2B—N1B	117.9 (3)	C11D—N3D—H3N7	120 (3)
C11B—N2B—H2NB	118 (3)	C11D—N3D—H3N8	116 (3)
N1B—N2B—H2NB	125 (3)	H3N7—N3D—H3N8	124 (5)
N3B—C11B—N2B	117.4 (3)	C1S—O1S—H1S	109.5
N3B—C11B—S2B	122.8 (3)	O1S—C1S—H1S1	109.5
N2B—C11B—S2B	119.8 (3)	O1S—C1S—H1S2	109.5
C11B—N3B—H3N3	116 (3)	H1S1—C1S—H1S2	109.5
C11B—N3B—H3N4	115 (3)	O1S—C1S—H1S3	109.5
H3N3—N3B—H3N4	129 (4)	H1S1—C1S—H1S3	109.5
C2C—C1C—C6C	121.8 (3)	H1S2—C1S—H1S3	109.5
C2C—C1C—S1C	126.7 (3)	C2S—O2S—H2S	109.5
C6C—C1C—S1C	111.5 (3)	O2S—C2S—H2S1	109.5
C3C—C2C—C1C	117.9 (4)	O2S—C2S—H2S2	109.5
C3C—C2C—H2C	121.1	H2S1—C2S—H2S2	109.5
C1C—C2C—H2C	121.1	O2S—C2S—H2S3	109.5
C2C—C3C—C4C	121.0 (4)	H2S1—C2S—H2S3	109.5
C2C—C3C—H3C	119.5	H2S2—C2S—H2S3	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3N2···N1A	0.843 (10)	2.29 (4)	2.641 (4)	105 (3)
N3B—H3N3···N1B	0.838 (10)	2.21 (4)	2.617 (4)	110 (3)
N3C—H3N5···N1C	0.842 (10)	2.22 (5)	2.543 (4)	102 (4)
N3D—H3N7···N1D	0.841 (10)	2.29 (5)	2.643 (4)	105 (4)
N3A—H3N1···S2Bii	0.839 (10)	2.500 (14)	3.325 (3)	168 (4)
N3B—H3N4···S2Aiii	0.839 (10)	2.62 (2)	3.367 (3)	149 (4)
N2B—H2NB···S2Aiv	0.839 (10)	2.585 (13)	3.412 (3)	169 (4)
N3C—H3N6···S2Av	0.840 (10)	2.76 (4)	3.352 (3)	129 (4)
N3C—H3N6···N3Bvi	0.840 (10)	2.72 (3)	3.468 (5)	149 (5)
N2C—H2NC···S2Cvii	0.842 (10)	2.60 (2)	3.392 (3)	158 (4)
N3D—H3N8···S2Av	0.840 (10)	2.738 (15)	3.563 (3)	168 (4)
N3D—H3N7···O1S	0.841 (10)	2.26 (3)	2.967 (6)	142 (4)
O1S—H1S···S2Cvii	0.84	2.64	3.471 (5)	169
O2S—H2S···S2Dviii	0.84	2.97	3.389 (6)	113
C3A—H3A···S2Av	0.95	2.97	3.762 (4)	142
C10A—H10A···S2Bix	0.98	2.91	3.613 (3)	129
C2B—H2B···O1Sx	0.95	2.36	3.282 (7)	163
C2S—H2S1···N2Dviii	0.98	2.74	3.266 (9)	115
C10B—H10F···Cgxi	0.98	2.91	3.594 (4)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H3N2⋯N1A	0.843 (10)	2.29 (4)	2.641 (4)	105 (3)
N3B—H3N3⋯N1B	0.838 (10)	2.21 (4)	2.617 (4)	110 (3)
N3C—H3N5⋯N1C	0.842 (10)	2.22 (5)	2.543 (4)	102 (4)
N3D—H3N7⋯N1D	0.841 (10)	2.29 (5)	2.643 (4)	105 (4)
N3A—H3N1⋯S2Bi	0.839 (10)	2.500 (14)	3.325 (3)	168 (4)
N3B—H3N4⋯S2Aii	0.839 (10)	2.62 (2)	3.367 (3)	149 (4)
N2B—H2NB⋯S2Aiii	0.839 (10)	2.585 (13)	3.412 (3)	169 (4)
N3C—H3N6⋯S2Aiv	0.840 (10)	2.76 (4)	3.352 (3)	129 (4)
N3C—H3N6⋯N3Bv	0.840 (10)	2.72 (3)	3.468 (5)	149 (5)
N2C—H2NC⋯S2Cvi	0.842 (10)	2.60 (2)	3.392 (3)	158 (4)
N3D—H3N8⋯S2Aiv	0.840 (10)	2.738 (15)	3.563 (3)	168 (4)
N3D—H3N7⋯O1S	0.841 (10)	2.26 (3)	2.967 (6)	142 (4)
O1S—H1S⋯S2Cvi	0.84	2.64	3.471 (5)	169
O2S—H2S⋯S2Dvii	0.84	2.97	3.389 (6)	113
C3A—H3A⋯S2Aiv	0.95	2.97	3.762 (4)	142
C10A—H10A⋯S2Bviii	0.98	2.91	3.613 (3)	129
C2B—H2B⋯O1Six	0.95	2.36	3.282 (7)	163
C2S—H2S1⋯N2Dvii	0.98	2.74	3.266 (9)	115
C10B—H10F⋯Cgx	0.98	2.91	3.594 (4)	129

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) . Cg is the centroid of C1B–C6B.