Crystal structure of (E)-N-cyclo­hexyl-2-(2-hy­droxy-3-methyl­benzyl­idene)hydrazine-1-carbo­thio­amide

The title Schiff base compound, consisting of a cyclo­hexane and a 2-hy­droxy-3-methyl­benzyl­idene ring bridged by a hydrazinecarbo­thio­amine moiety, crystallizes with two independent mol­ecules in the asymmetric unit. In the crystal, the mol­ecules are linked by N—H...S hydrogen bonds and C—H...π inter­actions, forming ribbons along the [010] direction.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.119
• Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT112_ALERT_2_C ADDSYM Detects New (Pseudo) Symm. Elem       a/2         80 %Fit
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.826 Check

Alert level G
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         16 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         77 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

(E)-N-Cyclohexyl-2-(2-hydroxy-3-methylbenzylidene)hydrazine-1-\ carbothioamide

Crystal data

C15H21N3OS	Z = 4
Mr = 291.41	F(000) = 624
Triclinic, P1	Dx = 1.295 Mg m^−3
a = 10.7799 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9481 (11) Å	Cell parameters from 6929 reflections
c = 14.1895 (15) Å	θ = 2.2–29.3°
α = 74.526 (2)°	µ = 0.22 mm^−1
β = 68.246 (1)°	T = 100 K
γ = 80.207 (2)°	Block, colourless
V = 1494.2 (3) Å^3	0.34 × 0.14 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	5805 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.069
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 29.4°, θmin = 1.6°
Tmin = 0.873, Tmax = 0.935	h = −14→14
50505 measured reflections	k = −15→15
8135 independent reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: mixed
wR(F^2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0524P)^2 + 0.3685P] where P = (Fo^2 + 2Fc^2)/3
8135 reflections	(Δ/σ)max = 0.001
387 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1A	0.69733 (4)	0.60902 (4)	0.10987 (3)	0.01869 (11)
O1A	0.20574 (12)	0.29193 (12)	0.27567 (9)	0.0204 (3)
H1O1	0.264 (2)	0.340 (2)	0.2474 (19)	0.047 (7)*
N1A	0.44459 (13)	0.36989 (12)	0.14267 (10)	0.0157 (3)
N2A	0.54998 (14)	0.44583 (13)	0.10122 (11)	0.0168 (3)
H1N2	0.617 (2)	0.4267 (19)	0.0507 (16)	0.032 (6)*
N3A	0.45512 (13)	0.54155 (13)	0.23929 (11)	0.0180 (3)
H1N3	0.387 (2)	0.5075 (19)	0.2500 (16)	0.031 (6)*
C1A	0.23068 (15)	0.20058 (15)	0.22090 (12)	0.0166 (3)
C2A	0.13421 (16)	0.11183 (15)	0.25585 (13)	0.0180 (3)
C3A	0.15680 (17)	0.01785 (16)	0.20070 (13)	0.0212 (4)
H3AA	0.0925	−0.0427	0.2231	0.025*
C4A	0.27061 (17)	0.00986 (16)	0.11389 (14)	0.0219 (4)
H4AA	0.2840	−0.0557	0.0779	0.026*
C5A	0.36387 (17)	0.09792 (16)	0.08048 (13)	0.0204 (3)
H5AA	0.4412	0.0933	0.0206	0.024*
C6A	0.34648 (16)	0.19418 (15)	0.13340 (12)	0.0163 (3)
C7A	0.45032 (16)	0.28267 (15)	0.09523 (13)	0.0173 (3)
H7AA	0.5243	0.2759	0.0337	0.021*
C8A	0.55885 (15)	0.52858 (15)	0.15423 (12)	0.0154 (3)
C9A	0.44553 (15)	0.62215 (16)	0.30920 (12)	0.0175 (3)
H9AA	0.5368	0.6226	0.3119	0.021*
C10A	0.39567 (17)	0.75839 (16)	0.27188 (14)	0.0223 (4)
H10A	0.3072	0.7594	0.2653	0.027*
H10B	0.4588	0.7950	0.2024	0.027*
C11A	0.38338 (17)	0.83900 (17)	0.34832 (14)	0.0249 (4)
H11A	0.4734	0.8448	0.3495	0.030*
H11B	0.3465	0.9261	0.3246	0.030*
C12A	0.29295 (17)	0.78223 (19)	0.45741 (15)	0.0300 (4)
H12A	0.2924	0.8328	0.5059	0.036*
H12B	0.2002	0.7864	0.4580	0.036*
C13A	0.3395 (2)	0.64536 (19)	0.49414 (14)	0.0334 (5)
H13A	0.2742	0.6092	0.5627	0.040*
H13B	0.4269	0.6425	0.5031	0.040*
C14A	0.35411 (18)	0.56458 (17)	0.41752 (13)	0.0253 (4)
H14A	0.3914	0.4777	0.4415	0.030*
H14B	0.2648	0.5581	0.4153	0.030*
C15A	0.01137 (16)	0.12174 (18)	0.34918 (14)	0.0246 (4)
H15A	−0.0495	0.0589	0.3588	0.037*
H15B	−0.0337	0.2073	0.3387	0.037*
H15C	0.0371	0.1055	0.4111	0.037*
S1B	1.20980 (4)	0.63000 (4)	0.11943 (3)	0.01957 (11)
O1B	0.72600 (12)	0.31105 (11)	0.27336 (9)	0.0204 (3)
H1O2	0.790 (2)	0.358 (2)	0.2455 (18)	0.042 (7)*
N1B	0.96393 (13)	0.38885 (13)	0.14385 (10)	0.0165 (3)
N2B	1.07086 (14)	0.46229 (13)	0.10739 (11)	0.0183 (3)
H2N2	1.141 (2)	0.4453 (19)	0.0585 (17)	0.035 (6)*
N3B	0.95163 (13)	0.58802 (14)	0.22201 (11)	0.0191 (3)
H2N3	0.8858 (19)	0.5517 (18)	0.2277 (14)	0.023 (5)*
C1B	0.74994 (15)	0.22243 (15)	0.21634 (12)	0.0160 (3)
C2B	0.64909 (16)	0.14034 (16)	0.24528 (13)	0.0182 (3)
C3B	0.67030 (16)	0.04933 (16)	0.18792 (13)	0.0212 (4)
H3BA	0.6019	−0.0055	0.2052	0.025*
C4B	0.78870 (17)	0.03605 (16)	0.10606 (14)	0.0221 (4)
H4BA	0.8018	−0.0285	0.0692	0.027*
C5B	0.88741 (16)	0.11750 (16)	0.07866 (13)	0.0198 (3)
H5BA	0.9683	0.1087	0.0224	0.024*
C6B	0.87008 (15)	0.21254 (15)	0.13242 (12)	0.0168 (3)
C7B	0.97581 (16)	0.29730 (15)	0.09955 (13)	0.0178 (3)
H7BA	1.0559	0.2846	0.0438	0.021*
C8B	1.06817 (16)	0.55741 (15)	0.15303 (12)	0.0165 (3)
C9B	0.93058 (15)	0.68143 (15)	0.28450 (12)	0.0171 (3)
H9BA	0.9867	0.7537	0.2406	0.021*
C10B	0.97252 (16)	0.62377 (16)	0.37971 (13)	0.0200 (3)
H10C	1.0684	0.5927	0.3570	0.024*
H10D	0.9197	0.5504	0.4230	0.024*
C11B	0.95005 (16)	0.72239 (16)	0.44436 (13)	0.0214 (4)
H11C	0.9730	0.6819	0.5077	0.026*
H11D	1.0100	0.7914	0.4034	0.026*
C12B	0.80487 (16)	0.77855 (17)	0.47574 (13)	0.0219 (4)
H12C	0.7460	0.7118	0.5248	0.026*
H12D	0.7953	0.8471	0.5120	0.026*
C13B	0.76067 (17)	0.83197 (17)	0.38142 (14)	0.0224 (4)
H13C	0.8111	0.9065	0.3372	0.027*
H13D	0.6642	0.8610	0.4051	0.027*
C14B	0.78417 (15)	0.73274 (16)	0.31723 (13)	0.0201 (4)
H14C	0.7268	0.6620	0.3590	0.024*
H14D	0.7592	0.7717	0.2546	0.024*
C15B	0.52399 (16)	0.15270 (17)	0.33654 (14)	0.0237 (4)
H15D	0.4569	0.1011	0.3383	0.036*
H15E	0.4886	0.2420	0.3299	0.036*
H15F	0.5447	0.1231	0.4010	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.01576 (19)	0.0224 (2)	0.0179 (2)	−0.00439 (16)	−0.00298 (16)	−0.00655 (17)
O1A	0.0200 (6)	0.0223 (7)	0.0185 (6)	−0.0050 (5)	−0.0019 (5)	−0.0086 (5)
N1A	0.0150 (6)	0.0159 (7)	0.0166 (7)	−0.0018 (5)	−0.0052 (5)	−0.0041 (5)
N2A	0.0155 (6)	0.0188 (7)	0.0155 (7)	−0.0032 (5)	−0.0014 (6)	−0.0072 (6)
N3A	0.0142 (6)	0.0223 (8)	0.0187 (7)	−0.0050 (6)	−0.0020 (6)	−0.0095 (6)
C1A	0.0199 (8)	0.0162 (8)	0.0153 (8)	−0.0006 (6)	−0.0079 (6)	−0.0036 (6)
C2A	0.0177 (7)	0.0191 (8)	0.0173 (8)	−0.0022 (6)	−0.0080 (6)	−0.0012 (7)
C3A	0.0238 (8)	0.0177 (9)	0.0244 (9)	−0.0054 (7)	−0.0118 (7)	−0.0013 (7)
C4A	0.0291 (9)	0.0168 (9)	0.0238 (9)	−0.0012 (7)	−0.0122 (7)	−0.0070 (7)
C5A	0.0238 (8)	0.0177 (9)	0.0187 (9)	0.0002 (7)	−0.0056 (7)	−0.0061 (7)
C6A	0.0197 (8)	0.0146 (8)	0.0151 (8)	−0.0009 (6)	−0.0074 (6)	−0.0025 (6)
C7A	0.0180 (7)	0.0175 (8)	0.0146 (8)	−0.0015 (6)	−0.0032 (6)	−0.0043 (6)
C8A	0.0158 (7)	0.0158 (8)	0.0153 (8)	−0.0003 (6)	−0.0072 (6)	−0.0024 (6)
C9A	0.0162 (7)	0.0223 (9)	0.0159 (8)	−0.0045 (6)	−0.0036 (6)	−0.0081 (7)
C10A	0.0248 (8)	0.0215 (9)	0.0225 (9)	−0.0012 (7)	−0.0091 (7)	−0.0072 (7)
C11A	0.0223 (8)	0.0248 (10)	0.0327 (10)	0.0003 (7)	−0.0109 (8)	−0.0142 (8)
C12A	0.0206 (8)	0.0435 (12)	0.0320 (11)	−0.0055 (8)	−0.0022 (8)	−0.0262 (9)
C13A	0.0415 (11)	0.0405 (12)	0.0187 (10)	−0.0133 (9)	−0.0027 (8)	−0.0120 (8)
C14A	0.0295 (9)	0.0272 (10)	0.0180 (9)	−0.0086 (8)	−0.0031 (7)	−0.0066 (7)
C15A	0.0198 (8)	0.0282 (10)	0.0244 (9)	−0.0067 (7)	−0.0040 (7)	−0.0056 (8)
S1B	0.01561 (19)	0.0223 (2)	0.0206 (2)	−0.00340 (16)	−0.00332 (16)	−0.00756 (17)
O1B	0.0204 (6)	0.0208 (6)	0.0198 (6)	−0.0032 (5)	−0.0019 (5)	−0.0106 (5)
N1B	0.0154 (6)	0.0169 (7)	0.0173 (7)	−0.0020 (5)	−0.0052 (5)	−0.0042 (6)
N2B	0.0155 (7)	0.0203 (8)	0.0177 (7)	−0.0029 (6)	−0.0013 (6)	−0.0074 (6)
N3B	0.0148 (6)	0.0217 (8)	0.0227 (8)	−0.0024 (6)	−0.0035 (6)	−0.0117 (6)
C1B	0.0185 (7)	0.0145 (8)	0.0151 (8)	0.0014 (6)	−0.0067 (6)	−0.0039 (6)
C2B	0.0179 (7)	0.0185 (8)	0.0176 (8)	−0.0002 (6)	−0.0072 (6)	−0.0022 (7)
C3B	0.0217 (8)	0.0200 (9)	0.0244 (9)	−0.0034 (7)	−0.0103 (7)	−0.0047 (7)
C4B	0.0275 (9)	0.0198 (9)	0.0246 (9)	−0.0003 (7)	−0.0117 (7)	−0.0109 (7)
C5B	0.0208 (8)	0.0211 (9)	0.0176 (8)	0.0000 (7)	−0.0041 (7)	−0.0095 (7)
C6B	0.0179 (7)	0.0171 (8)	0.0163 (8)	−0.0011 (6)	−0.0066 (6)	−0.0042 (6)
C7B	0.0175 (7)	0.0186 (8)	0.0158 (8)	0.0003 (6)	−0.0042 (6)	−0.0049 (7)
C8B	0.0186 (7)	0.0160 (8)	0.0142 (8)	−0.0011 (6)	−0.0059 (6)	−0.0021 (6)
C9B	0.0178 (7)	0.0179 (8)	0.0167 (8)	−0.0032 (6)	−0.0035 (6)	−0.0079 (7)
C10B	0.0183 (8)	0.0215 (9)	0.0199 (9)	0.0017 (6)	−0.0066 (7)	−0.0063 (7)
C11B	0.0228 (8)	0.0252 (9)	0.0188 (9)	−0.0011 (7)	−0.0096 (7)	−0.0063 (7)
C12B	0.0225 (8)	0.0247 (9)	0.0196 (9)	−0.0005 (7)	−0.0062 (7)	−0.0092 (7)
C13B	0.0207 (8)	0.0245 (9)	0.0262 (10)	0.0035 (7)	−0.0107 (7)	−0.0121 (8)
C14B	0.0179 (8)	0.0236 (9)	0.0218 (9)	−0.0006 (7)	−0.0081 (7)	−0.0087 (7)
C15B	0.0199 (8)	0.0253 (9)	0.0231 (9)	−0.0036 (7)	−0.0036 (7)	−0.0048 (7)

Geometric parameters (Å, º)

S1A—C8A	1.6897 (15)	S1B—C8B	1.6914 (16)
O1A—C1A	1.3583 (19)	O1B—C1B	1.3569 (19)
O1A—H1O1	0.80 (2)	O1B—H1O2	0.83 (2)
N1A—C7A	1.289 (2)	N1B—C7B	1.284 (2)
N1A—N2A	1.3758 (18)	N1B—N2B	1.3762 (18)
N2A—C8A	1.357 (2)	N2B—C8B	1.357 (2)
N2A—H1N2	0.85 (2)	N2B—H2N2	0.85 (2)
N3A—C8A	1.328 (2)	N3B—C8B	1.330 (2)
N3A—C9A	1.461 (2)	N3B—C9B	1.463 (2)
N3A—H1N3	0.82 (2)	N3B—H2N3	0.840 (19)
C1A—C6A	1.404 (2)	C1B—C2B	1.401 (2)
C1A—C2A	1.406 (2)	C1B—C6B	1.409 (2)
C2A—C3A	1.390 (2)	C2B—C3B	1.387 (2)
C2A—C15A	1.499 (2)	C2B—C15B	1.500 (2)
C3A—C4A	1.390 (2)	C3B—C4B	1.388 (2)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.378 (2)	C4B—C5B	1.382 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.400 (2)	C5B—C6B	1.397 (2)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.458 (2)	C6B—C7B	1.453 (2)
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C9A—C14A	1.517 (2)	C9B—C14B	1.522 (2)
C9A—C10A	1.520 (2)	C9B—C10B	1.526 (2)
C9A—H9AA	1.0000	C9B—H9BA	1.0000
C10A—C11A	1.529 (2)	C10B—C11B	1.530 (2)
C10A—H10A	0.9900	C10B—H10C	0.9900
C10A—H10B	0.9900	C10B—H10D	0.9900
C11A—C12A	1.519 (3)	C11B—C12B	1.526 (2)
C11A—H11A	0.9900	C11B—H11C	0.9900
C11A—H11B	0.9900	C11B—H11D	0.9900
C12A—C13A	1.513 (3)	C12B—C13B	1.523 (2)
C12A—H12A	0.9900	C12B—H12C	0.9900
C12A—H12B	0.9900	C12B—H12D	0.9900
C13A—C14A	1.526 (2)	C13B—C14B	1.529 (2)
C13A—H13A	0.9900	C13B—H13C	0.9900
C13A—H13B	0.9900	C13B—H13D	0.9900
C14A—H14A	0.9900	C14B—H14C	0.9900
C14A—H14B	0.9900	C14B—H14D	0.9900
C15A—H15A	0.9800	C15B—H15D	0.9800
C15A—H15B	0.9800	C15B—H15E	0.9800
C15A—H15C	0.9800	C15B—H15F	0.9800
C1A—O1A—H1O1	108.6 (17)	C1B—O1B—H1O2	107.4 (15)
C7A—N1A—N2A	116.82 (13)	C7B—N1B—N2B	116.97 (14)
C8A—N2A—N1A	119.82 (13)	C8B—N2B—N1B	120.46 (14)
C8A—N2A—H1N2	120.7 (13)	C8B—N2B—H2N2	119.4 (14)
N1A—N2A—H1N2	117.8 (14)	N1B—N2B—H2N2	120.0 (14)
C8A—N3A—C9A	125.71 (13)	C8B—N3B—C9B	124.99 (13)
C8A—N3A—H1N3	117.1 (14)	C8B—N3B—H2N3	116.0 (13)
C9A—N3A—H1N3	116.9 (14)	C9B—N3B—H2N3	118.9 (13)
O1A—C1A—C6A	122.24 (14)	O1B—C1B—C2B	116.63 (14)
O1A—C1A—C2A	116.68 (14)	O1B—C1B—C6B	122.02 (14)
C6A—C1A—C2A	121.08 (15)	C2B—C1B—C6B	121.35 (15)
C3A—C2A—C1A	117.85 (15)	C3B—C2B—C1B	117.95 (15)
C3A—C2A—C15A	122.40 (14)	C3B—C2B—C15B	122.57 (15)
C1A—C2A—C15A	119.74 (15)	C1B—C2B—C15B	119.48 (15)
C4A—C3A—C2A	122.00 (15)	C2B—C3B—C4B	121.87 (15)
C4A—C3A—H3AA	119.0	C2B—C3B—H3BA	119.1
C2A—C3A—H3AA	119.0	C4B—C3B—H3BA	119.1
C5A—C4A—C3A	119.37 (16)	C5B—C4B—C3B	119.48 (15)
C5A—C4A—H4AA	120.3	C5B—C4B—H4BA	120.3
C3A—C4A—H4AA	120.3	C3B—C4B—H4BA	120.3
C4A—C5A—C6A	121.01 (16)	C4B—C5B—C6B	120.98 (16)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.5
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.5
C5A—C6A—C1A	118.68 (14)	C5B—C6B—C1B	118.35 (14)
C5A—C6A—C7A	118.22 (15)	C5B—C6B—C7B	118.96 (15)
C1A—C6A—C7A	123.09 (14)	C1B—C6B—C7B	122.70 (14)
N1A—C7A—C6A	121.83 (15)	N1B—C7B—C6B	121.80 (15)
N1A—C7A—H7AA	119.1	N1B—C7B—H7BA	119.1
C6A—C7A—H7AA	119.1	C6B—C7B—H7BA	119.1
N3A—C8A—N2A	116.73 (14)	N3B—C8B—N2B	116.78 (14)
N3A—C8A—S1A	123.76 (12)	N3B—C8B—S1B	124.07 (12)
N2A—C8A—S1A	119.51 (12)	N2B—C8B—S1B	119.15 (12)
N3A—C9A—C14A	108.61 (13)	N3B—C9B—C14B	109.69 (12)
N3A—C9A—C10A	112.01 (13)	N3B—C9B—C10B	111.20 (13)
C14A—C9A—C10A	111.06 (14)	C14B—C9B—C10B	110.58 (13)
N3A—C9A—H9AA	108.4	N3B—C9B—H9BA	108.4
C14A—C9A—H9AA	108.4	C14B—C9B—H9BA	108.4
C10A—C9A—H9AA	108.4	C10B—C9B—H9BA	108.4
C9A—C10A—C11A	110.55 (14)	C9B—C10B—C11B	110.68 (13)
C9A—C10A—H10A	109.5	C9B—C10B—H10C	109.5
C11A—C10A—H10A	109.5	C11B—C10B—H10C	109.5
C9A—C10A—H10B	109.5	C9B—C10B—H10D	109.5
C11A—C10A—H10B	109.5	C11B—C10B—H10D	109.5
H10A—C10A—H10B	108.1	H10C—C10B—H10D	108.1
C12A—C11A—C10A	111.31 (14)	C12B—C11B—C10B	111.23 (13)
C12A—C11A—H11A	109.4	C12B—C11B—H11C	109.4
C10A—C11A—H11A	109.4	C10B—C11B—H11C	109.4
C12A—C11A—H11B	109.4	C12B—C11B—H11D	109.4
C10A—C11A—H11B	109.4	C10B—C11B—H11D	109.4
H11A—C11A—H11B	108.0	H11C—C11B—H11D	108.0
C13A—C12A—C11A	111.40 (15)	C13B—C12B—C11B	111.49 (14)
C13A—C12A—H12A	109.3	C13B—C12B—H12C	109.3
C11A—C12A—H12A	109.3	C11B—C12B—H12C	109.3
C13A—C12A—H12B	109.3	C13B—C12B—H12D	109.3
C11A—C12A—H12B	109.3	C11B—C12B—H12D	109.3
H12A—C12A—H12B	108.0	H12C—C12B—H12D	108.0
C12A—C13A—C14A	111.91 (16)	C12B—C13B—C14B	111.59 (14)
C12A—C13A—H13A	109.2	C12B—C13B—H13C	109.3
C14A—C13A—H13A	109.2	C14B—C13B—H13C	109.3
C12A—C13A—H13B	109.2	C12B—C13B—H13D	109.3
C14A—C13A—H13B	109.2	C14B—C13B—H13D	109.3
H13A—C13A—H13B	107.9	H13C—C13B—H13D	108.0
C9A—C14A—C13A	111.02 (14)	C9B—C14B—C13B	110.42 (13)
C9A—C14A—H14A	109.4	C9B—C14B—H14C	109.6
C13A—C14A—H14A	109.4	C13B—C14B—H14C	109.6
C9A—C14A—H14B	109.4	C9B—C14B—H14D	109.6
C13A—C14A—H14B	109.4	C13B—C14B—H14D	109.6
H14A—C14A—H14B	108.0	H14C—C14B—H14D	108.1
C2A—C15A—H15A	109.5	C2B—C15B—H15D	109.5
C2A—C15A—H15B	109.5	C2B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C2A—C15A—H15C	109.5	C2B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C7A—N1A—N2A—C8A	−171.68 (14)	C7B—N1B—N2B—C8B	−177.23 (14)
O1A—C1A—C2A—C3A	179.53 (14)	O1B—C1B—C2B—C3B	179.53 (14)
C6A—C1A—C2A—C3A	−0.3 (2)	C6B—C1B—C2B—C3B	−0.7 (2)
O1A—C1A—C2A—C15A	0.2 (2)	O1B—C1B—C2B—C15B	−1.0 (2)
C6A—C1A—C2A—C15A	−179.68 (15)	C6B—C1B—C2B—C15B	178.77 (15)
C1A—C2A—C3A—C4A	0.3 (2)	C1B—C2B—C3B—C4B	1.9 (2)
C15A—C2A—C3A—C4A	179.61 (16)	C15B—C2B—C3B—C4B	−177.57 (16)
C2A—C3A—C4A—C5A	−0.5 (3)	C2B—C3B—C4B—C5B	−1.7 (3)
C3A—C4A—C5A—C6A	0.8 (3)	C3B—C4B—C5B—C6B	0.3 (3)
C4A—C5A—C6A—C1A	−0.9 (2)	C4B—C5B—C6B—C1B	0.8 (2)
C4A—C5A—C6A—C7A	178.73 (15)	C4B—C5B—C6B—C7B	−178.94 (15)
O1A—C1A—C6A—C5A	−179.23 (14)	O1B—C1B—C6B—C5B	179.16 (14)
C2A—C1A—C6A—C5A	0.6 (2)	C2B—C1B—C6B—C5B	−0.6 (2)
O1A—C1A—C6A—C7A	1.2 (2)	O1B—C1B—C6B—C7B	−1.1 (2)
C2A—C1A—C6A—C7A	−178.96 (14)	C2B—C1B—C6B—C7B	179.12 (15)
N2A—N1A—C7A—C6A	178.28 (13)	N2B—N1B—C7B—C6B	179.20 (14)
C5A—C6A—C7A—N1A	−176.61 (15)	C5B—C6B—C7B—N1B	177.83 (15)
C1A—C6A—C7A—N1A	3.0 (2)	C1B—C6B—C7B—N1B	−1.9 (2)
C9A—N3A—C8A—N2A	178.07 (14)	C9B—N3B—C8B—N2B	175.59 (14)
C9A—N3A—C8A—S1A	−2.3 (2)	C9B—N3B—C8B—S1B	−4.8 (2)
N1A—N2A—C8A—N3A	−7.4 (2)	N1B—N2B—C8B—N3B	−10.2 (2)
N1A—N2A—C8A—S1A	172.92 (11)	N1B—N2B—C8B—S1B	170.21 (11)
C8A—N3A—C9A—C14A	−151.70 (16)	C8B—N3B—C9B—C14B	155.77 (15)
C8A—N3A—C9A—C10A	85.26 (19)	C8B—N3B—C9B—C10B	−81.60 (19)
N3A—C9A—C10A—C11A	178.51 (13)	N3B—C9B—C10B—C11B	179.99 (13)
C14A—C9A—C10A—C11A	56.87 (18)	C14B—C9B—C10B—C11B	−57.90 (17)
C9A—C10A—C11A—C12A	−56.18 (19)	C9B—C10B—C11B—C12B	55.88 (18)
C10A—C11A—C12A—C13A	54.83 (19)	C10B—C11B—C12B—C13B	−54.08 (19)
C11A—C12A—C13A—C14A	−54.1 (2)	C11B—C12B—C13B—C14B	54.32 (19)
N3A—C9A—C14A—C13A	−179.67 (15)	N3B—C9B—C14B—C13B	−179.21 (14)
C10A—C9A—C14A—C13A	−56.06 (19)	C10B—C9B—C14B—C13B	57.79 (18)
C12A—C13A—C14A—C9A	54.7 (2)	C12B—C13B—C14B—C9B	−56.10 (19)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of benzene ring C1A–C6A.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.80 (2)	1.98 (2)	2.6844 (19)	146 (2)
O1B—H1O2···N1B	0.84 (2)	1.91 (2)	2.664 (2)	148 (2)
N2A—H1N2···S1B^i	0.85 (2)	2.60 (2)	3.4414 (16)	170 (2)
N2B—H2N2···S1A^i	0.85 (2)	2.53 (2)	3.3568 (15)	164 (2)
C11A—H11B···Cg1^ii	0.99	2.93	3.801 (2)	148

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