Dicyclo-hexyl-ammonium thio-cyanate: monoclinic polymorph.

The title salt, C(12)H(24)N(+)·NCS(-), represents a monoclinic polymorph of the previously reported ortho-rhom-bic form [Khawar Rauf et al. (2008 ▶). Acta Cryst. E64, o366]. Two independent formula units comprise the asymmetric unit with the major difference in their mol-ecular structures relating to the relative dispositions of the cyclo-hexyl rings [dihedral angles = 79.88 (6) and 67.72 (5)°]. Further, the independent anions form distinctive patterns of hydrogen-bonding inter-actions, i.e. 2 × N-H⋯N versus N-H⋯N and N-H⋯S. The resulting supra-molecular architecture is a supra-molecular chain along the c axis based on a square-wave topology.

Related literature

For the crystal structure of the ortho­rhom­bic polymorph, see: Khawar Rauf et al. (2008 ▶). For additional structure analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C12H24N+·NCS−

M = 240.40

Monoclinic,

a = 8.5190 (1) Å

b = 37.9428 (5) Å

c = 8.5578 (1) Å

β = 93.661 (1)°

V = 2760.53 (6) Å3

Z = 8

Cu Kα radiation

μ = 1.88 mm−1

T = 100 K

0.30 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.602, T max = 0.704

16974 measured reflections

5693 independent reflections

5363 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.02

5693 reflections

305 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), QMol (Gans & Shalloway, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040001/hg5105sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040001/hg5105Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040001/hg5105Isup3.cml

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

C12H24N+·NCS−	F(000) = 1056
Mr = 240.40	Dx = 1.157 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 9471 reflections
a = 8.5190 (1) Å	θ = 3.5–76.6°
b = 37.9428 (5) Å	µ = 1.88 mm−1
c = 8.5578 (1) Å	T = 100 K
β = 93.661 (1)°	Prism, colourless
V = 2760.53 (6) Å3	0.30 × 0.30 × 0.20 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	5693 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5363 reflections with I > 2σ(I)
Mirror	Rint = 0.020
Detector resolution: 10.4041 pixels mm-1	θmax = 75.0°, θmin = 5.2°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −45→47
Tmin = 0.602, Tmax = 0.704	l = −9→10
16974 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.9255P] where P = (Fo2 + 2Fc2)/3
5693 reflections	(Δ/σ)max = 0.002
305 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.25 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
S1	0.09309 (3)	0.325069 (7)	0.66579 (3)	0.02219 (8)
S2	0.73345 (3)	0.424830 (7)	0.97466 (3)	0.02176 (8)
N1	0.24296 (10)	0.37649 (2)	0.18494 (11)	0.01476 (18)
N2	0.59395 (10)	0.38563 (2)	0.64295 (10)	0.01326 (17)
N3	0.25785 (10)	0.38031 (2)	0.53216 (10)	0.01739 (19)
N4	0.57319 (11)	0.37474 (3)	1.14655 (11)	0.0213 (2)
C1	0.18788 (12)	0.41052 (3)	0.10828 (12)	0.0154 (2)
H1	0.0728	0.4134	0.1215	0.018*
C2	0.21502 (14)	0.41008 (3)	−0.06624 (12)	0.0192 (2)
H2A	0.1487	0.3916	−0.1187	0.023*
H2B	0.3265	0.4043	−0.0810	0.023*
C3	0.17461 (15)	0.44596 (3)	−0.14073 (13)	0.0231 (2)
H3A	0.2005	0.4456	−0.2519	0.028*
H3B	0.0602	0.4502	−0.1377	0.028*
C4	0.26455 (16)	0.47591 (3)	−0.05596 (14)	0.0251 (2)
H4A	0.3787	0.4730	−0.0673	0.030*
H4B	0.2319	0.4987	−0.1038	0.030*
C5	0.23223 (15)	0.47606 (3)	0.11732 (13)	0.0233 (2)
H5A	0.2940	0.4951	0.1714	0.028*
H5B	0.1193	0.4809	0.1288	0.028*
C6	0.27613 (13)	0.44066 (3)	0.19307 (12)	0.0178 (2)
H6A	0.2502	0.4410	0.3042	0.021*
H6B	0.3908	0.4368	0.1898	0.021*
C7	0.16086 (12)	0.34292 (3)	0.13194 (12)	0.0166 (2)
H7	0.1640	0.3409	0.0157	0.020*
C8	−0.01021 (13)	0.34341 (3)	0.17372 (14)	0.0212 (2)
H8A	−0.0661	0.3632	0.1189	0.025*
H8B	−0.0153	0.3470	0.2878	0.025*
C9	−0.08997 (14)	0.30851 (3)	0.12608 (16)	0.0269 (3)
H9A	−0.1996	0.3087	0.1581	0.032*
H9B	−0.0933	0.3060	0.0108	0.032*
C10	−0.00232 (15)	0.27727 (3)	0.20182 (17)	0.0279 (3)
H10A	−0.0537	0.2551	0.1655	0.033*
H10B	−0.0072	0.2786	0.3169	0.033*
C11	0.16942 (15)	0.27704 (3)	0.16025 (16)	0.0275 (3)
H11A	0.1745	0.2734	0.0461	0.033*
H11B	0.2253	0.2572	0.2147	0.033*
C12	0.25028 (13)	0.31181 (3)	0.20785 (14)	0.0205 (2)
H12A	0.2544	0.3143	0.3232	0.025*
H12B	0.3595	0.3117	0.1748	0.025*
C13	0.66417 (12)	0.40923 (3)	0.52378 (12)	0.0133 (2)
H13	0.6382	0.3993	0.4170	0.016*
C14	0.58766 (12)	0.44545 (3)	0.53387 (12)	0.0156 (2)
H14A	0.6065	0.4550	0.6411	0.019*
H14B	0.4726	0.4434	0.5110	0.019*
C15	0.65691 (13)	0.47051 (3)	0.41591 (13)	0.0184 (2)
H15A	0.6320	0.4617	0.3083	0.022*
H15B	0.6089	0.4941	0.4245	0.022*
C16	0.83523 (13)	0.47332 (3)	0.44655 (13)	0.0198 (2)
H16A	0.8785	0.4891	0.3678	0.024*
H16B	0.8600	0.4836	0.5515	0.024*
C17	0.91103 (13)	0.43707 (3)	0.43778 (13)	0.0197 (2)
H17A	1.0257	0.4392	0.4625	0.024*
H17B	0.8946	0.4279	0.3297	0.024*
C18	0.84242 (12)	0.41101 (3)	0.55173 (13)	0.0173 (2)
H18A	0.8881	0.3873	0.5370	0.021*
H18B	0.8701	0.4186	0.6607	0.021*
C19	0.64807 (12)	0.34769 (3)	0.65169 (12)	0.0141 (2)
H19	0.7622	0.3470	0.6872	0.017*
C20	0.62609 (13)	0.33067 (3)	0.49062 (12)	0.0164 (2)
H20A	0.6962	0.3422	0.4182	0.020*
H20B	0.5161	0.3340	0.4485	0.020*
C21	0.66374 (14)	0.29126 (3)	0.50033 (13)	0.0200 (2)
H21A	0.6432	0.2804	0.3958	0.024*
H21B	0.7767	0.2881	0.5319	0.024*
C22	0.56472 (14)	0.27271 (3)	0.61790 (13)	0.0215 (2)
H22A	0.4521	0.2742	0.5821	0.026*
H22B	0.5941	0.2475	0.6244	0.026*
C23	0.59016 (14)	0.28959 (3)	0.77911 (13)	0.0207 (2)
H23A	0.7007	0.2860	0.8189	0.025*
H23B	0.5214	0.2780	0.8526	0.025*
C24	0.55370 (13)	0.32905 (3)	0.77289 (12)	0.0176 (2)
H24A	0.4400	0.3325	0.7462	0.021*
H24B	0.5791	0.3396	0.8773	0.021*
C25	0.18777 (12)	0.35743 (3)	0.58834 (12)	0.0165 (2)
C26	0.64060 (12)	0.39560 (3)	1.07589 (12)	0.0161 (2)
H11	0.2359 (16)	0.3784 (4)	0.2875 (18)	0.021 (3)*
H12	0.3529 (19)	0.3737 (4)	0.1698 (17)	0.028 (4)*
H21	0.4878 (18)	0.3857 (4)	0.6218 (16)	0.021 (3)*
H22	0.6162 (18)	0.3952 (4)	0.7374 (18)	0.026 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01980 (14)	0.01931 (14)	0.02743 (15)	−0.00320 (10)	0.00126 (11)	0.00326 (10)
S2	0.02543 (15)	0.02238 (14)	0.01734 (14)	−0.00632 (10)	0.00034 (10)	0.00057 (10)
N1	0.0141 (4)	0.0151 (4)	0.0149 (4)	−0.0022 (3)	0.0002 (3)	−0.0004 (3)
N2	0.0136 (4)	0.0112 (4)	0.0149 (4)	0.0000 (3)	0.0004 (3)	−0.0006 (3)
N3	0.0156 (4)	0.0193 (4)	0.0171 (4)	0.0009 (3)	−0.0003 (3)	0.0006 (3)
N4	0.0176 (4)	0.0264 (5)	0.0197 (5)	−0.0008 (4)	0.0010 (4)	0.0001 (4)
C1	0.0149 (5)	0.0152 (5)	0.0158 (5)	−0.0008 (4)	0.0000 (4)	−0.0001 (4)
C2	0.0250 (5)	0.0176 (5)	0.0149 (5)	−0.0016 (4)	−0.0008 (4)	−0.0009 (4)
C3	0.0318 (6)	0.0196 (5)	0.0173 (5)	−0.0018 (5)	−0.0031 (5)	0.0022 (4)
C4	0.0354 (7)	0.0179 (5)	0.0218 (6)	−0.0054 (5)	−0.0003 (5)	0.0033 (4)
C5	0.0318 (6)	0.0155 (5)	0.0224 (6)	−0.0023 (4)	−0.0001 (5)	−0.0018 (4)
C6	0.0203 (5)	0.0165 (5)	0.0164 (5)	−0.0028 (4)	0.0001 (4)	−0.0022 (4)
C7	0.0168 (5)	0.0153 (5)	0.0175 (5)	−0.0037 (4)	−0.0001 (4)	−0.0018 (4)
C8	0.0144 (5)	0.0176 (5)	0.0312 (6)	−0.0019 (4)	−0.0018 (4)	0.0001 (4)
C9	0.0189 (5)	0.0239 (6)	0.0374 (7)	−0.0073 (5)	−0.0032 (5)	−0.0024 (5)
C10	0.0249 (6)	0.0164 (5)	0.0425 (7)	−0.0068 (5)	0.0036 (5)	−0.0021 (5)
C11	0.0256 (6)	0.0160 (5)	0.0414 (7)	−0.0015 (5)	0.0058 (5)	−0.0056 (5)
C12	0.0162 (5)	0.0165 (5)	0.0288 (6)	0.0001 (4)	0.0016 (4)	−0.0008 (4)
C13	0.0142 (5)	0.0119 (5)	0.0137 (5)	−0.0009 (4)	0.0013 (4)	0.0003 (4)
C14	0.0144 (5)	0.0122 (5)	0.0204 (5)	−0.0002 (4)	0.0013 (4)	0.0005 (4)
C15	0.0172 (5)	0.0141 (5)	0.0238 (5)	−0.0007 (4)	0.0005 (4)	0.0041 (4)
C16	0.0181 (5)	0.0187 (5)	0.0225 (5)	−0.0059 (4)	0.0008 (4)	0.0026 (4)
C17	0.0138 (5)	0.0241 (6)	0.0215 (5)	−0.0010 (4)	0.0034 (4)	0.0029 (4)
C18	0.0136 (5)	0.0177 (5)	0.0205 (5)	0.0013 (4)	0.0012 (4)	0.0021 (4)
C19	0.0144 (5)	0.0098 (5)	0.0176 (5)	0.0007 (4)	−0.0019 (4)	0.0000 (4)
C20	0.0206 (5)	0.0130 (5)	0.0158 (5)	−0.0007 (4)	0.0017 (4)	−0.0005 (4)
C21	0.0265 (6)	0.0122 (5)	0.0214 (5)	−0.0003 (4)	0.0024 (4)	−0.0029 (4)
C22	0.0304 (6)	0.0127 (5)	0.0211 (5)	−0.0034 (4)	−0.0009 (5)	0.0002 (4)
C23	0.0300 (6)	0.0137 (5)	0.0181 (5)	−0.0001 (4)	−0.0019 (4)	0.0029 (4)
C24	0.0231 (5)	0.0146 (5)	0.0149 (5)	0.0004 (4)	0.0004 (4)	0.0012 (4)
C25	0.0133 (5)	0.0196 (5)	0.0161 (5)	0.0035 (4)	−0.0021 (4)	−0.0024 (4)
C26	0.0132 (5)	0.0207 (5)	0.0142 (5)	0.0026 (4)	−0.0015 (4)	−0.0040 (4)

S1—C25	1.6327 (11)	C10—H10B	0.9900
S2—C26	1.6412 (11)	C11—C12	1.5314 (15)
N1—C7	1.5087 (13)	C11—H11A	0.9900
N1—C1	1.5097 (13)	C11—H11B	0.9900
N1—H11	0.887 (15)	C12—H12A	0.9900
N1—H12	0.960 (16)	C12—H12B	0.9900
N2—C13	1.5090 (13)	C13—C18	1.5236 (14)
N2—C19	1.5120 (12)	C13—C14	1.5260 (13)
N2—H21	0.911 (15)	C13—H13	1.0000
N2—H22	0.895 (16)	C14—C15	1.5319 (14)
N3—C25	1.1738 (15)	C14—H14A	0.9900
N4—C26	1.1690 (15)	C14—H14B	0.9900
C1—C2	1.5259 (14)	C15—C16	1.5287 (15)
C1—C6	1.5264 (14)	C15—H15A	0.9900
C1—H1	1.0000	C15—H15B	0.9900
C2—C3	1.5329 (15)	C16—C17	1.5235 (16)
C2—H2A	0.9900	C16—H16A	0.9900
C2—H2B	0.9900	C16—H16B	0.9900
C3—C4	1.5278 (16)	C17—C18	1.5305 (14)
C3—H3A	0.9900	C17—H17A	0.9900
C3—H3B	0.9900	C17—H17B	0.9900
C4—C5	1.5255 (16)	C18—H18A	0.9900
C4—H4A	0.9900	C18—H18B	0.9900
C4—H4B	0.9900	C19—C20	1.5230 (14)
C5—C6	1.5274 (15)	C19—C24	1.5262 (14)
C5—H5A	0.9900	C19—H19	1.0000
C5—H5B	0.9900	C20—C21	1.5303 (14)
C6—H6A	0.9900	C20—H20A	0.9900
C6—H6B	0.9900	C20—H20B	0.9900
C7—C8	1.5227 (15)	C21—C22	1.5257 (15)
C7—C12	1.5273 (15)	C21—H21A	0.9900
C7—H7	1.0000	C21—H21B	0.9900
C8—C9	1.5317 (15)	C22—C23	1.5240 (15)
C8—H8A	0.9900	C22—H22A	0.9900
C8—H8B	0.9900	C22—H22B	0.9900
C9—C10	1.5235 (17)	C23—C24	1.5290 (14)
C9—H9A	0.9900	C23—H23A	0.9900
C9—H9B	0.9900	C23—H23B	0.9900
C10—C11	1.5277 (17)	C24—H24A	0.9900
C10—H10A	0.9900	C24—H24B	0.9900
C7—N1—C1	117.79 (8)	C7—C12—H12A	109.6
C7—N1—H11	108.0 (9)	C11—C12—H12A	109.6
C1—N1—H11	108.7 (9)	C7—C12—H12B	109.6
C7—N1—H12	107.6 (9)	C11—C12—H12B	109.6
C1—N1—H12	108.4 (9)	H12A—C12—H12B	108.1
H11—N1—H12	105.8 (13)	N2—C13—C18	110.76 (8)
C13—N2—C19	117.74 (8)	N2—C13—C14	107.88 (8)
C13—N2—H21	107.2 (9)	C18—C13—C14	112.09 (8)
C19—N2—H21	107.9 (9)	N2—C13—H13	108.7
C13—N2—H22	107.4 (10)	C18—C13—H13	108.7
C19—N2—H22	107.2 (10)	C14—C13—H13	108.7
H21—N2—H22	109.2 (13)	C13—C14—C15	109.75 (8)
N1—C1—C2	110.71 (8)	C13—C14—H14A	109.7
N1—C1—C6	107.72 (8)	C15—C14—H14A	109.7
C2—C1—C6	111.89 (9)	C13—C14—H14B	109.7
N1—C1—H1	108.8	C15—C14—H14B	109.7
C2—C1—H1	108.8	H14A—C14—H14B	108.2
C6—C1—H1	108.8	C16—C15—C14	110.52 (9)
C1—C2—C3	110.68 (9)	C16—C15—H15A	109.5
C1—C2—H2A	109.5	C14—C15—H15A	109.5
C3—C2—H2A	109.5	C16—C15—H15B	109.5
C1—C2—H2B	109.5	C14—C15—H15B	109.5
C3—C2—H2B	109.5	H15A—C15—H15B	108.1
H2A—C2—H2B	108.1	C17—C16—C15	110.38 (9)
C4—C3—C2	111.76 (9)	C17—C16—H16A	109.6
C4—C3—H3A	109.3	C15—C16—H16A	109.6
C2—C3—H3A	109.3	C17—C16—H16B	109.6
C4—C3—H3B	109.3	C15—C16—H16B	109.6
C2—C3—H3B	109.3	H16A—C16—H16B	108.1
H3A—C3—H3B	107.9	C16—C17—C18	111.81 (9)
C5—C4—C3	110.38 (10)	C16—C17—H17A	109.3
C5—C4—H4A	109.6	C18—C17—H17A	109.3
C3—C4—H4A	109.6	C16—C17—H17B	109.3
C5—C4—H4B	109.6	C18—C17—H17B	109.3
C3—C4—H4B	109.6	H17A—C17—H17B	107.9
H4A—C4—H4B	108.1	C13—C18—C17	110.24 (9)
C6—C5—C4	110.78 (9)	C13—C18—H18A	109.6
C6—C5—H5A	109.5	C17—C18—H18A	109.6
C4—C5—H5A	109.5	C13—C18—H18B	109.6
C6—C5—H5B	109.5	C17—C18—H18B	109.6
C4—C5—H5B	109.5	H18A—C18—H18B	108.1
H5A—C5—H5B	108.1	N2—C19—C20	109.85 (8)
C5—C6—C1	110.93 (9)	N2—C19—C24	107.63 (8)
C5—C6—H6A	109.5	C20—C19—C24	112.26 (8)
C1—C6—H6A	109.5	N2—C19—H19	109.0
C5—C6—H6B	109.5	C20—C19—H19	109.0
C1—C6—H6B	109.5	C24—C19—H19	109.0
H6A—C6—H6B	108.0	C19—C20—C21	110.61 (9)
N1—C7—C8	110.57 (9)	C19—C20—H20A	109.5
N1—C7—C12	108.39 (8)	C21—C20—H20A	109.5
C8—C7—C12	111.61 (9)	C19—C20—H20B	109.5
N1—C7—H7	108.7	C21—C20—H20B	109.5
C8—C7—H7	108.7	H20A—C20—H20B	108.1
C12—C7—H7	108.7	C22—C21—C20	111.33 (9)
C7—C8—C9	110.00 (9)	C22—C21—H21A	109.4
C7—C8—H8A	109.7	C20—C21—H21A	109.4
C9—C8—H8A	109.7	C22—C21—H21B	109.4
C7—C8—H8B	109.7	C20—C21—H21B	109.4
C9—C8—H8B	109.7	H21A—C21—H21B	108.0
H8A—C8—H8B	108.2	C23—C22—C21	110.51 (9)
C10—C9—C8	111.25 (10)	C23—C22—H22A	109.5
C10—C9—H9A	109.4	C21—C22—H22A	109.5
C8—C9—H9A	109.4	C23—C22—H22B	109.5
C10—C9—H9B	109.4	C21—C22—H22B	109.5
C8—C9—H9B	109.4	H22A—C22—H22B	108.1
H9A—C9—H9B	108.0	C22—C23—C24	111.30 (9)
C9—C10—C11	110.86 (10)	C22—C23—H23A	109.4
C9—C10—H10A	109.5	C24—C23—H23A	109.4
C11—C10—H10A	109.5	C22—C23—H23B	109.4
C9—C10—H10B	109.5	C24—C23—H23B	109.4
C11—C10—H10B	109.5	H23A—C23—H23B	108.0
H10A—C10—H10B	108.1	C19—C24—C23	111.28 (9)
C10—C11—C12	110.75 (10)	C19—C24—H24A	109.4
C10—C11—H11A	109.5	C23—C24—H24A	109.4
C12—C11—H11A	109.5	C19—C24—H24B	109.4
C10—C11—H11B	109.5	C23—C24—H24B	109.4
C12—C11—H11B	109.5	H24A—C24—H24B	108.0
H11A—C11—H11B	108.1	N3—C25—S1	178.87 (10)
C7—C12—C11	110.43 (9)	N4—C26—S2	179.22 (10)
C7—N1—C1—C2	−63.27 (11)	C19—N2—C13—C18	−58.85 (11)
C7—N1—C1—C6	174.10 (9)	C19—N2—C13—C14	178.14 (8)
N1—C1—C2—C3	−174.30 (9)	N2—C13—C14—C15	179.34 (8)
C6—C1—C2—C3	−54.13 (12)	C18—C13—C14—C15	57.15 (11)
C1—C2—C3—C4	54.77 (13)	C13—C14—C15—C16	−57.84 (11)
C2—C3—C4—C5	−56.51 (14)	C14—C15—C16—C17	57.81 (12)
C3—C4—C5—C6	57.23 (13)	C15—C16—C17—C18	−56.46 (12)
C4—C5—C6—C1	−56.84 (13)	N2—C13—C18—C17	−175.91 (8)
N1—C1—C6—C5	177.42 (9)	C14—C13—C18—C17	−55.37 (11)
C2—C1—C6—C5	55.53 (12)	C16—C17—C18—C13	54.81 (12)
C1—N1—C7—C8	−65.18 (12)	C13—N2—C19—C20	−54.20 (11)
C1—N1—C7—C12	172.18 (9)	C13—N2—C19—C24	−176.70 (8)
N1—C7—C8—C9	−177.40 (9)	N2—C19—C20—C21	−174.01 (8)
C12—C7—C8—C9	−56.65 (13)	C24—C19—C20—C21	−54.29 (12)
C7—C8—C9—C10	56.46 (14)	C19—C20—C21—C22	55.96 (12)
C8—C9—C10—C11	−56.77 (14)	C20—C21—C22—C23	−57.26 (12)
C9—C10—C11—C12	56.41 (15)	C21—C22—C23—C24	56.46 (13)
N1—C7—C12—C11	178.84 (9)	N2—C19—C24—C23	174.89 (8)
C8—C7—C12—C11	56.83 (12)	C20—C19—C24—C23	53.89 (12)
C10—C11—C12—C7	−56.15 (14)	C22—C23—C24—C19	−54.72 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N3	0.887 (15)	2.091 (15)	2.9696 (13)	170.6 (13)
N1—H12···N4i	0.960 (16)	1.900 (16)	2.8539 (13)	172.1 (13)
N2—H21···N3	0.911 (15)	2.068 (15)	2.9650 (12)	168.1 (13)
N2—H22···S2	0.895 (16)	2.475 (16)	3.3544 (9)	167.4 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯N3	0.887 (15)	2.091 (15)	2.9696 (13)	170.6 (13)
N1—H12⋯N4i	0.960 (16)	1.900 (16)	2.8539 (13)	172.1 (13)
N2—H21⋯N3	0.911 (15)	2.068 (15)	2.9650 (12)	168.1 (13)
N2—H22⋯S2	0.895 (16)	2.475 (16)	3.3544 (9)	167.4 (13)

Symmetry code: (i) .