Octyl (2E)-2-[2-(di-phenyl-phosphan-yl)benzyl-idene]hydrazinecarbodi-thio-ate.

The title compound, C28H33N2S2P, adopts the thione tautomeric form, as supported by the C-S distance [1.6744 (18) Å]. The Schiff base exhibits an E conformation about the C=N bond but a Z conformation about the C-N bond. The terminal chain is disordered over two sets of sites with an occupancy ratio of 0.732 (3):0.268 (3). In the crystal, pairs of N-N-H hydrogen bonds between the thione groups link neighbouring mol-ecules into centrosymmetric dimers.

Related literature

For Schiff bases derived from S-alk­yl/aryl esters of di­thio­carbazic acid, see: Akbar Ali et al. (2012 ▶, 2013 ▶); Hamid et al. (2009 ▶); Akbar Ali et al. (2005 ▶). For their chemotherapeutic properties, see: Tarafder et al. (2002 ▶); Akbar Ali & Livingstone (1974 ▶); Akbar Ali et al. (2002 ▶); Hossain et al. (1996 ▶). For related structures, see: Su et al. (1999 ▶); Song et al. (2009 ▶); Shanmuga Sundara Raj et al. (2000 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C28H33N2PS2

M = 492.65

Triclinic,

a = 11.2068 (12) Å

b = 11.4956 (12) Å

c = 11.7728 (13) Å

α = 86.623 (1)°

β = 70.538 (1)°

γ = 65.013 (1)°

V = 1290.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.60 × 0.60 × 0.38 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.846, T max = 0.899

15526 measured reflections

5343 independent reflections

4954 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.04

5343 reflections

356 parameters

209 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.30 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814008459/bq2394sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008459/bq2394Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008459/bq2394Isup3.cml

CCDC reference: 997277

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H33N2PS2	Z = 2
Mr = 492.65	F(000) = 524
Triclinic, P1	Dx = 1.268 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.2068 (12) Å	Cell parameters from 5343 reflections
b = 11.4956 (12) Å	θ = 2.2–28.3°
c = 11.7728 (13) Å	µ = 0.29 mm−1
α = 86.623 (1)°	T = 100 K
β = 70.538 (1)°	Block, yellow
γ = 65.013 (1)°	0.60 × 0.60 × 0.38 mm
V = 1290.2 (2) Å3

Bruker APEXII CCD diffractometer	5343 independent reflections
Radiation source: fine-focus sealed tube	4954 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −14→14
Tmin = 0.846, Tmax = 0.899	k = −14→14
15526 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0483P)2 + 1.3326P] where P = (Fo2 + 2Fc2)/3
5343 reflections	(Δ/σ)max = 0.001
356 parameters	Δρmax = 1.30 e Å−3
209 restraints	Δρmin = −0.51 e Å−3

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	Occ. (<1)
P1	−0.07934 (5)	1.15477 (4)	1.32348 (4)	0.01927 (12)
S1	0.51929 (5)	0.64877 (4)	0.91914 (4)	0.02410 (13)
S2	0.66997 (5)	0.81091 (5)	0.92999 (5)	0.02737 (13)
N1	0.28051 (15)	0.86048 (15)	1.05097 (14)	0.0193 (3)
N2	0.39950 (16)	0.87988 (15)	1.02654 (14)	0.0207 (3)
C1	−0.09012 (18)	1.03671 (16)	1.23193 (15)	0.0172 (3)
C2	−0.21642 (19)	1.02936 (18)	1.24981 (17)	0.0219 (4)
H2	−0.2996	1.0883	1.3089	0.026*
C3	−0.2230 (2)	0.93807 (19)	1.18325 (17)	0.0230 (4)
H3	−0.3103	0.9358	1.1961	0.028*
C4	−0.1020 (2)	0.84996 (18)	1.09786 (16)	0.0214 (4)
H4	−0.1060	0.7867	1.0526	0.026*
C5	0.02430 (19)	0.85474 (17)	1.07898 (16)	0.0199 (4)
H5	0.1070	0.7942	1.0206	0.024*
C6	0.03213 (18)	0.94745 (16)	1.14455 (15)	0.0165 (3)
C7	0.16737 (18)	0.95264 (17)	1.11708 (16)	0.0187 (4)
H7	0.1710	1.0248	1.1485	0.022*
C8	0.52454 (19)	0.78826 (17)	0.96203 (16)	0.0199 (4)
C1A	−0.13142 (18)	1.30012 (17)	1.24425 (15)	0.0187 (4)
C2A	−0.0523 (2)	1.37020 (19)	1.22768 (17)	0.0242 (4)
H2A	0.0230	1.3421	1.2581	0.029*
C3A	−0.0827 (2)	1.4809 (2)	1.16693 (19)	0.0289 (4)
H3A	−0.0281	1.5279	1.1561	0.035*
C4A	−0.1920 (2)	1.52279 (19)	1.12225 (18)	0.0271 (4)
H4A	−0.2129	1.5985	1.0810	0.033*
C5A	−0.2713 (2)	1.45323 (19)	1.13810 (17)	0.0249 (4)
H5A	−0.3465	1.4817	1.1075	0.030*
C6A	−0.24120 (19)	1.34284 (18)	1.19809 (16)	0.0218 (4)
H6A	−0.2956	1.2957	1.2080	0.026*
C1B	−0.23181 (19)	1.18714 (18)	1.46050 (16)	0.0208 (4)
C2B	−0.3553 (2)	1.30064 (19)	1.49289 (18)	0.0265 (4)
H2B	−0.3669	1.3667	1.4396	0.032*
C3B	−0.4615 (2)	1.3177 (2)	1.60282 (19)	0.0316 (5)
H3B	−0.5449	1.3957	1.6243	0.038*
C4B	−0.4468 (2)	1.2223 (2)	1.68103 (18)	0.0303 (4)
H4B	−0.5199	1.2341	1.7557	0.036*
C5B	−0.3244 (2)	1.1093 (2)	1.64970 (18)	0.0288 (4)
H5B	−0.3137	1.0430	1.7028	0.035*
C6B	−0.2177 (2)	1.09262 (19)	1.54106 (17)	0.0244 (4)
H6B	−0.1335	1.0154	1.5212	0.029*
C9	0.6997 (2)	0.5511 (2)	0.82747 (19)	0.0296 (4)
H9A	0.7349	0.6020	0.7657	0.035*
H9B	0.7592	0.5220	0.8789	0.035*
C10	0.7045 (2)	0.4366 (2)	0.7671 (2)	0.0341 (5)
H10A	0.6483	0.4675	0.7130	0.041*
H10B	0.6607	0.3918	0.8299	0.041*
C11	0.8511 (3)	0.3413 (3)	0.6941 (3)	0.0277 (5)	0.732 (3)
H11A	0.8469	0.2631	0.6684	0.033*	0.732 (3)
H11B	0.9089	0.3156	0.7470	0.033*	0.732 (3)
C12	0.9238 (3)	0.3919 (3)	0.5817 (2)	0.0290 (4)	0.732 (3)
H12A	0.8692	0.4133	0.5263	0.035*	0.732 (3)
H12B	0.9250	0.4721	0.6063	0.035*	0.732 (3)
C13	1.0739 (3)	0.2945 (3)	0.5141 (3)	0.0291 (4)	0.732 (3)
H13A	1.0747	0.2090	0.5059	0.035*	0.732 (3)
H13B	1.1049	0.3203	0.4316	0.035*	0.732 (3)
C14	1.1788 (4)	0.2821 (3)	0.5752 (3)	0.0300 (4)	0.732 (3)
H14A	1.1396	0.2724	0.6621	0.036*	0.732 (3)
H14B	1.1915	0.3627	0.5697	0.036*	0.732 (3)
C15	1.3220 (3)	0.1684 (3)	0.5202 (3)	0.0312 (4)	0.732 (3)
H15A	1.3815	0.1636	0.5680	0.037*	0.732 (3)
H15B	1.3094	0.0877	0.5267	0.037*	0.732 (3)
C16	1.3971 (4)	0.1766 (4)	0.3891 (3)	0.0338 (5)	0.732 (3)
H16A	1.4981	0.1246	0.3693	0.051*	0.732 (3)
H16B	1.3789	0.2666	0.3757	0.051*	0.732 (3)
H16C	1.3633	0.1440	0.3372	0.051*	0.732 (3)
C11X	0.8421 (8)	0.3668 (9)	0.6579 (8)	0.0285 (6)	0.268 (3)
H11C	0.8566	0.2765	0.6465	0.034*	0.268 (3)
H11D	0.8273	0.4080	0.5845	0.034*	0.268 (3)
C12X	0.9771 (7)	0.3637 (7)	0.6639 (6)	0.0290 (5)	0.268 (3)
H12C	0.9746	0.4507	0.6527	0.035*	0.268 (3)
H12D	0.9824	0.3424	0.7453	0.035*	0.268 (3)
C13X	1.1062 (8)	0.2679 (8)	0.5704 (7)	0.0292 (5)	0.268 (3)
H13C	1.0997	0.2891	0.4893	0.035*	0.268 (3)
H13D	1.1081	0.1812	0.5822	0.035*	0.268 (3)
C14X	1.2442 (9)	0.2622 (8)	0.5726 (7)	0.0304 (5)	0.268 (3)
H14C	1.2471	0.2498	0.6557	0.036*	0.268 (3)
H14D	1.2477	0.3456	0.5516	0.036*	0.268 (3)
C15X	1.3729 (10)	0.1538 (9)	0.4851 (8)	0.0316 (5)	0.268 (3)
H15C	1.3658	0.0711	0.5020	0.038*	0.268 (3)
H15D	1.4577	0.1471	0.4992	0.038*	0.268 (3)
C16X	1.3887 (11)	0.1750 (11)	0.3520 (8)	0.0325 (6)	0.268 (3)
H16D	1.4877	0.1310	0.3017	0.049*	0.268 (3)
H16E	1.3540	0.2676	0.3426	0.049*	0.268 (3)
H16F	1.3345	0.1401	0.3266	0.049*	0.268 (3)
H2N	0.391 (3)	0.9588 (18)	1.044 (2)	0.039*

	U11	U22	U33	U12	U13	U23
P1	0.0189 (2)	0.0175 (2)	0.0191 (2)	−0.00565 (18)	−0.00590 (18)	−0.00221 (17)
S1	0.0163 (2)	0.0228 (2)	0.0291 (3)	−0.00693 (18)	−0.00338 (18)	−0.00559 (18)
S2	0.0158 (2)	0.0252 (2)	0.0388 (3)	−0.00881 (19)	−0.0055 (2)	−0.0017 (2)
N1	0.0158 (7)	0.0212 (7)	0.0198 (7)	−0.0079 (6)	−0.0047 (6)	0.0030 (6)
N2	0.0159 (7)	0.0207 (8)	0.0233 (8)	−0.0081 (6)	−0.0032 (6)	−0.0009 (6)
C1	0.0182 (8)	0.0156 (8)	0.0168 (8)	−0.0061 (7)	−0.0061 (7)	0.0019 (6)
C2	0.0170 (8)	0.0236 (9)	0.0210 (9)	−0.0061 (7)	−0.0044 (7)	−0.0019 (7)
C3	0.0205 (9)	0.0280 (10)	0.0236 (9)	−0.0127 (8)	−0.0084 (7)	0.0029 (7)
C4	0.0267 (9)	0.0211 (9)	0.0195 (9)	−0.0114 (8)	−0.0097 (7)	0.0014 (7)
C5	0.0200 (9)	0.0187 (8)	0.0165 (8)	−0.0053 (7)	−0.0043 (7)	0.0001 (7)
C6	0.0171 (8)	0.0152 (8)	0.0156 (8)	−0.0058 (7)	−0.0055 (7)	0.0035 (6)
C7	0.0188 (8)	0.0183 (8)	0.0174 (8)	−0.0070 (7)	−0.0051 (7)	0.0009 (7)
C8	0.0181 (8)	0.0218 (9)	0.0188 (9)	−0.0079 (7)	−0.0056 (7)	0.0017 (7)
C1A	0.0177 (8)	0.0166 (8)	0.0160 (8)	−0.0046 (7)	−0.0018 (7)	−0.0031 (6)
C2A	0.0192 (9)	0.0255 (9)	0.0254 (9)	−0.0089 (8)	−0.0049 (7)	−0.0014 (7)
C3A	0.0280 (10)	0.0274 (10)	0.0306 (11)	−0.0161 (8)	−0.0035 (8)	0.0022 (8)
C4A	0.0275 (10)	0.0222 (9)	0.0232 (10)	−0.0081 (8)	−0.0019 (8)	0.0027 (7)
C5A	0.0223 (9)	0.0249 (9)	0.0214 (9)	−0.0051 (8)	−0.0062 (7)	−0.0011 (7)
C6A	0.0210 (9)	0.0208 (9)	0.0213 (9)	−0.0080 (7)	−0.0047 (7)	−0.0025 (7)
C1B	0.0233 (9)	0.0217 (9)	0.0180 (8)	−0.0093 (7)	−0.0075 (7)	−0.0026 (7)
C2B	0.0295 (10)	0.0206 (9)	0.0223 (9)	−0.0068 (8)	−0.0050 (8)	0.0003 (7)
C3B	0.0292 (11)	0.0275 (10)	0.0268 (10)	−0.0067 (9)	−0.0017 (8)	−0.0050 (8)
C4B	0.0330 (11)	0.0373 (11)	0.0194 (9)	−0.0182 (9)	−0.0023 (8)	−0.0029 (8)
C5B	0.0404 (12)	0.0321 (11)	0.0205 (9)	−0.0194 (9)	−0.0136 (9)	0.0050 (8)
C6B	0.0278 (10)	0.0227 (9)	0.0239 (9)	−0.0092 (8)	−0.0119 (8)	0.0003 (7)
C9	0.0179 (9)	0.0297 (10)	0.0315 (11)	−0.0047 (8)	−0.0017 (8)	−0.0103 (8)
C10	0.0303 (11)	0.0306 (11)	0.0379 (12)	−0.0156 (9)	−0.0027 (9)	−0.0054 (9)
C11	0.0291 (8)	0.0263 (8)	0.0242 (9)	−0.0103 (7)	−0.0065 (7)	0.0001 (7)
C12	0.0290 (8)	0.0285 (7)	0.0249 (8)	−0.0094 (6)	−0.0069 (6)	−0.0004 (6)
C13	0.0285 (8)	0.0301 (7)	0.0248 (8)	−0.0096 (7)	−0.0077 (7)	−0.0009 (6)
C14	0.0287 (8)	0.0320 (7)	0.0256 (7)	−0.0103 (7)	−0.0079 (7)	−0.0006 (6)
C15	0.0282 (8)	0.0351 (7)	0.0265 (9)	−0.0106 (7)	−0.0082 (7)	0.0002 (7)
C16	0.0282 (9)	0.0390 (8)	0.0280 (10)	−0.0099 (7)	−0.0074 (8)	0.0006 (8)
C11X	0.0290 (9)	0.0283 (9)	0.0249 (10)	−0.0101 (8)	−0.0073 (8)	−0.0015 (8)
C12X	0.0288 (8)	0.0294 (7)	0.0250 (8)	−0.0100 (7)	−0.0073 (7)	−0.0008 (7)
C13X	0.0284 (8)	0.0305 (7)	0.0251 (8)	−0.0100 (7)	−0.0077 (7)	−0.0006 (7)
C14X	0.0283 (9)	0.0332 (8)	0.0260 (9)	−0.0104 (8)	−0.0078 (8)	−0.0001 (7)
C15X	0.0284 (9)	0.0352 (8)	0.0265 (9)	−0.0103 (7)	−0.0077 (8)	0.0000 (7)
C16X	0.0285 (9)	0.0370 (9)	0.0268 (10)	−0.0104 (8)	−0.0076 (9)	0.0000 (9)

P1—C1B	1.8322 (19)	C9—C10	1.505 (3)
P1—C1A	1.8325 (18)	C9—H9A	0.9900
P1—C1	1.8481 (18)	C9—H9B	0.9900
S1—C8	1.7391 (19)	C10—C11	1.513 (4)
S1—C9	1.8120 (19)	C10—C11X	1.559 (8)
S2—C8	1.6744 (18)	C10—H10A	0.9900
N1—C7	1.281 (2)	C10—H10B	0.9900
N1—N2	1.378 (2)	C11—C12	1.531 (4)
N2—C8	1.337 (2)	C11—H11A	0.9900
N2—H2N	0.898 (17)	C11—H11B	0.9900
C1—C2	1.398 (3)	C12—C13	1.529 (4)
C1—C6	1.409 (2)	C12—H12A	0.9900
C2—C3	1.386 (3)	C12—H12B	0.9900
C2—H2	0.9500	C13—C14	1.526 (4)
C3—C4	1.388 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.382 (3)	C14—C15	1.529 (4)
C4—H4	0.9500	C14—H14A	0.9900
C5—C6	1.400 (2)	C14—H14B	0.9900
C5—H5	0.9500	C15—C16	1.511 (4)
C6—C7	1.467 (2)	C15—H15A	0.9900
C7—H7	0.9500	C15—H15B	0.9900
C1A—C2A	1.394 (3)	C16—H16A	0.9800
C1A—C6A	1.398 (3)	C16—H16B	0.9800
C2A—C3A	1.391 (3)	C16—H16C	0.9800
C2A—H2A	0.9500	C11X—C12X	1.524 (9)
C3A—C4A	1.382 (3)	C11X—H11C	0.9900
C3A—H3A	0.9500	C11X—H11D	0.9900
C4A—C5A	1.391 (3)	C12X—C13X	1.501 (8)
C4A—H4A	0.9500	C12X—H12C	0.9900
C5A—C6A	1.384 (3)	C12X—H12D	0.9900
C5A—H5A	0.9500	C13X—C14X	1.528 (9)
C6A—H6A	0.9500	C13X—H13C	0.9900
C1B—C6B	1.392 (3)	C13X—H13D	0.9900
C1B—C2B	1.394 (3)	C14X—C15X	1.529 (9)
C2B—C3B	1.392 (3)	C14X—H14C	0.9900
C2B—H2B	0.9500	C14X—H14D	0.9900
C3B—C4B	1.381 (3)	C15X—C16X	1.534 (10)
C3B—H3B	0.9500	C15X—H15C	0.9900
C4B—C5B	1.385 (3)	C15X—H15D	0.9900
C4B—H4B	0.9500	C16X—H16D	0.9800
C5B—C6B	1.385 (3)	C16X—H16E	0.9800
C5B—H5B	0.9500	C16X—H16F	0.9800
C6B—H6B	0.9500
C1B—P1—C1A	104.27 (8)	C11—C10—H10A	108.8
C1B—P1—C1	101.59 (8)	C9—C10—H10B	108.8
C1A—P1—C1	102.39 (8)	C11—C10—H10B	108.8
C8—S1—C9	102.85 (9)	H10A—C10—H10B	107.7
C7—N1—N2	114.84 (15)	C10—C11—C12	114.6 (2)
C8—N2—N1	120.21 (15)	C10—C11—H11A	108.6
C8—N2—H2N	120.0 (17)	C12—C11—H11A	108.6
N1—N2—H2N	119.0 (17)	C10—C11—H11B	108.6
C2—C1—C6	118.18 (16)	C12—C11—H11B	108.6
C2—C1—P1	121.83 (13)	H11A—C11—H11B	107.6
C6—C1—P1	119.94 (13)	C13—C12—C11	112.7 (2)
C3—C2—C1	121.53 (17)	C13—C12—H12A	109.1
C3—C2—H2	119.2	C11—C12—H12A	109.1
C1—C2—H2	119.2	C13—C12—H12B	109.1
C2—C3—C4	119.95 (17)	C11—C12—H12B	109.1
C2—C3—H3	120.0	H12A—C12—H12B	107.8
C4—C3—H3	120.0	C14—C13—C12	114.3 (2)
C5—C4—C3	119.64 (17)	C14—C13—H13A	108.7
C5—C4—H4	120.2	C12—C13—H13A	108.7
C3—C4—H4	120.2	C14—C13—H13B	108.7
C4—C5—C6	120.99 (16)	C12—C13—H13B	108.7
C4—C5—H5	119.5	H13A—C13—H13B	107.6
C6—C5—H5	119.5	C13—C14—C15	113.8 (2)
C5—C6—C1	119.71 (16)	C13—C14—H14A	108.8
C5—C6—C7	118.94 (15)	C15—C14—H14A	108.8
C1—C6—C7	121.30 (16)	C13—C14—H14B	108.8
N1—C7—C6	120.42 (16)	C15—C14—H14B	108.8
N1—C7—H7	119.8	H14A—C14—H14B	107.7
C6—C7—H7	119.8	C16—C15—C14	113.9 (3)
N2—C8—S2	120.86 (14)	C16—C15—H15A	108.8
N2—C8—S1	114.09 (13)	C14—C15—H15A	108.8
S2—C8—S1	125.05 (11)	C16—C15—H15B	108.8
C2A—C1A—C6A	118.71 (17)	C14—C15—H15B	108.8
C2A—C1A—P1	116.43 (14)	H15A—C15—H15B	107.7
C6A—C1A—P1	124.85 (14)	C15—C16—H16A	109.5
C3A—C2A—C1A	120.56 (18)	C15—C16—H16B	109.5
C3A—C2A—H2A	119.7	H16A—C16—H16B	109.5
C1A—C2A—H2A	119.7	C15—C16—H16C	109.5
C4A—C3A—C2A	120.29 (19)	H16A—C16—H16C	109.5
C4A—C3A—H3A	119.9	H16B—C16—H16C	109.5
C2A—C3A—H3A	119.9	C12X—C11X—C10	118.2 (6)
C3A—C4A—C5A	119.53 (18)	C12X—C11X—H11C	107.8
C3A—C4A—H4A	120.2	C10—C11X—H11C	107.8
C5A—C4A—H4A	120.2	C12X—C11X—H11D	107.8
C6A—C5A—C4A	120.40 (18)	C10—C11X—H11D	107.8
C6A—C5A—H5A	119.8	H11C—C11X—H11D	107.1
C4A—C5A—H5A	119.8	C13X—C12X—C11X	113.2 (7)
C5A—C6A—C1A	120.51 (18)	C13X—C12X—H12C	108.9
C5A—C6A—H6A	119.7	C11X—C12X—H12C	108.9
C1A—C6A—H6A	119.7	C13X—C12X—H12D	108.9
C6B—C1B—C2B	118.33 (18)	C11X—C12X—H12D	108.9
C6B—C1B—P1	116.22 (14)	H12C—C12X—H12D	107.7
C2B—C1B—P1	125.33 (15)	C12X—C13X—C14X	115.0 (7)
C3B—C2B—C1B	120.41 (19)	C12X—C13X—H13C	108.5
C3B—C2B—H2B	119.8	C14X—C13X—H13C	108.5
C1B—C2B—H2B	119.8	C12X—C13X—H13D	108.5
C4B—C3B—C2B	120.60 (19)	C14X—C13X—H13D	108.5
C4B—C3B—H3B	119.7	H13C—C13X—H13D	107.5
C2B—C3B—H3B	119.7	C13X—C14X—C15X	113.0 (7)
C3B—C4B—C5B	119.42 (19)	C13X—C14X—H14C	109.0
C3B—C4B—H4B	120.3	C15X—C14X—H14C	109.0
C5B—C4B—H4B	120.3	C13X—C14X—H14D	109.0
C4B—C5B—C6B	120.14 (19)	C15X—C14X—H14D	109.0
C4B—C5B—H5B	119.9	H14C—C14X—H14D	107.8
C6B—C5B—H5B	119.9	C14X—C15X—C16X	112.8 (8)
C5B—C6B—C1B	121.09 (18)	C14X—C15X—H15C	109.0
C5B—C6B—H6B	119.5	C16X—C15X—H15C	109.0
C1B—C6B—H6B	119.5	C14X—C15X—H15D	109.0
C10—C9—S1	107.87 (14)	C16X—C15X—H15D	109.0
C10—C9—H9A	110.1	H15C—C15X—H15D	107.8
S1—C9—H9A	110.1	C15X—C16X—H16D	109.5
C10—C9—H9B	110.1	C15X—C16X—H16E	109.5
S1—C9—H9B	110.1	H16D—C16X—H16E	109.5
H9A—C9—H9B	108.4	C15X—C16X—H16F	109.5
C9—C10—C11	113.6 (2)	H16D—C16X—H16F	109.5
C9—C10—C11X	113.2 (4)	H16E—C16X—H16F	109.5
C9—C10—H10A	108.8
C7—N1—N2—C8	177.59 (16)	C3A—C4A—C5A—C6A	0.0 (3)
C1B—P1—C1—C2	23.69 (17)	C4A—C5A—C6A—C1A	0.4 (3)
C1A—P1—C1—C2	−83.93 (16)	C2A—C1A—C6A—C5A	−0.6 (3)
C1B—P1—C1—C6	−153.73 (14)	P1—C1A—C6A—C5A	−179.15 (14)
C1A—P1—C1—C6	98.65 (14)	C1A—P1—C1B—C6B	−177.27 (14)
C6—C1—C2—C3	−0.6 (3)	C1—P1—C1B—C6B	76.58 (15)
P1—C1—C2—C3	−178.08 (14)	C1A—P1—C1B—C2B	−1.38 (19)
C1—C2—C3—C4	1.0 (3)	C1—P1—C1B—C2B	−107.53 (17)
C2—C3—C4—C5	−0.6 (3)	C6B—C1B—C2B—C3B	−0.4 (3)
C3—C4—C5—C6	−0.2 (3)	P1—C1B—C2B—C3B	−176.25 (16)
C4—C5—C6—C1	0.6 (3)	C1B—C2B—C3B—C4B	−0.5 (3)
C4—C5—C6—C7	−177.04 (16)	C2B—C3B—C4B—C5B	0.5 (3)
C2—C1—C6—C5	−0.2 (2)	C3B—C4B—C5B—C6B	0.3 (3)
P1—C1—C6—C5	177.34 (13)	C4B—C5B—C6B—C1B	−1.3 (3)
C2—C1—C6—C7	177.37 (16)	C2B—C1B—C6B—C5B	1.3 (3)
P1—C1—C6—C7	−5.1 (2)	P1—C1B—C6B—C5B	177.49 (15)
N2—N1—C7—C6	176.72 (15)	C8—S1—C9—C10	−170.42 (15)
C5—C6—C7—N1	−12.7 (3)	S1—C9—C10—C11	−175.95 (19)
C1—C6—C7—N1	169.78 (16)	S1—C9—C10—C11X	163.0 (4)
N1—N2—C8—S2	179.22 (13)	C9—C10—C11—C12	−67.3 (3)
N1—N2—C8—S1	−1.6 (2)	C11X—C10—C11—C12	25.7 (11)
C9—S1—C8—N2	176.61 (14)	C10—C11—C12—C13	177.4 (2)
C9—S1—C8—S2	−4.25 (15)	C11—C12—C13—C14	−75.4 (3)
C1B—P1—C1A—C2A	117.75 (14)	C12—C13—C14—C15	169.6 (3)
C1—P1—C1A—C2A	−136.70 (14)	C13—C14—C15—C16	62.2 (4)
C1B—P1—C1A—C6A	−63.64 (17)	C9—C10—C11X—C12X	33.4 (8)
C1—P1—C1A—C6A	41.91 (17)	C11—C10—C11X—C12X	−62.1 (11)
C6A—C1A—C2A—C3A	0.4 (3)	C10—C11X—C12X—C13X	165.7 (7)
P1—C1A—C2A—C3A	179.05 (15)	C11X—C12X—C13X—C14X	179.6 (7)
C1A—C2A—C3A—C4A	0.0 (3)	C12X—C13X—C14X—C15X	173.9 (7)
C2A—C3A—C4A—C5A	−0.2 (3)	C13X—C14X—C15X—C16X	66.9 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S2i	0.90 (2)	2.45 (2)	3.3337 (17)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S2i	0.90 (2)	2.45 (2)	3.3337 (17)	168 (2)

Symmetry code: (i) .