3-(Adamantan-1-yl)-4-methyl-1-[(4-phenyl-piperazin-1-yl)meth-yl]-1H-1,2,4-triazole-5(4H)-thione dichloro-methane hemisolvate.

The asymmetric unit of the title dichloro-methane hemisolvate, C(24)H(33)N(5)S·0.5CH(2)Cl(2), comprises an adamantan-yl/triazole derivative and half a CH(2)Cl(2) mol-ecule of crystallization; the latter is disordered about a twofold axis of symmetry. The piperazine ring has a chair conformation and the two N-bound substituents occupy equatorial positions. The piperazine residue is almost normal to the triazole ring [N-N-C-N torsion angle = -79.9 (3)°] so that to a first approximation, the mol-ecule has an L-shape. Linear supra-molecular chains parallel to [001] are formed via C-H⋯S inter-actions. Two such chains are linked into a double chain via C-H⋯Cl inter-actions involving the disordered CH(2)Cl(2) mol-ecules of solvation.

Related literature

For the diverse biological activities of adamantane derivatives, see: Al-Deeb et al. (2006 ▶); Al-Omar et al. (2010 ▶). For related adamantanyl structural studies, see: El-Emam et al. (2012a ▶,b ▶). For the preparation of one of the precursor mol­ecules, see: El-Emam & Ibrahim (1991 ▶).

Experimental

Crystal data

2C24H33N5S·CH2Cl2

M = 932.17

Orthorhombic,

a = 66.8490 (16) Å

b = 22.1076 (4) Å

c = 6.5109 (1) Å

V = 9622.3 (3) Å3

Z = 8

Cu Kα radiation

μ = 2.38 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.752, T max = 1.000

18884 measured reflections

4509 independent reflections

4437 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.09

4509 reflections

299 parameters

19 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −1.00 e Å−3

Absolute structure: Flack (1983 ▶), 1772 Friedel pairs

Flack parameter: −0.002 (17)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021393/hg5226sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021393/hg5226Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021393/hg5226Isup3.cml

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

2C24H33N5S·CH2Cl2	F(000) = 3984
Mr = 932.17	Dx = 1.287 Mg m−3
Orthorhombic, Fdd2	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: F 2 -2d	Cell parameters from 10015 reflections
a = 66.8490 (16) Å	θ = 2.6–76.4°
b = 22.1076 (4) Å	µ = 2.38 mm−1
c = 6.5109 (1) Å	T = 100 K
V = 9622.3 (3) Å3	Prism, colourless
Z = 8	0.30 × 0.20 × 0.10 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	4509 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4437 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 2.6°
ω scan	h = −84→80
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −25→27
Tmin = 0.752, Tmax = 1.000	l = −7→8
18884 measured reflections

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0825P)2 + 16.7617P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.002
4509 reflections	Δρmax = 0.41 e Å−3
299 parameters	Δρmin = −1.00 e Å−3
19 restraints	Absolute structure: Flack (1983), 1772 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.002 (17)

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)
S1	0.106131 (8)	0.22602 (2)	0.50061 (10)	0.02473 (15)
N1	0.09696 (3)	0.34338 (8)	0.4049 (3)	0.0198 (4)
N2	0.08323 (3)	0.33690 (8)	0.0966 (3)	0.0218 (4)
N3	0.08877 (3)	0.28044 (8)	0.1693 (3)	0.0219 (4)
N4	0.06533 (3)	0.20162 (8)	0.0489 (3)	0.0223 (4)
N5	0.02334 (3)	0.19119 (9)	0.1251 (3)	0.0256 (4)
C1	0.08658 (3)	0.44216 (9)	0.2235 (3)	0.0183 (4)
C2	0.07497 (4)	0.45691 (10)	0.0251 (4)	0.0256 (5)
H2A	0.0818	0.4383	−0.0939	0.031*
H2B	0.0613	0.4396	0.0337	0.031*
C3	0.07361 (4)	0.52562 (10)	−0.0064 (5)	0.0262 (5)
H3	0.0661	0.5343	−0.1362	0.031*
C4	0.09476 (4)	0.55174 (10)	−0.0222 (4)	0.0252 (5)
H4A	0.0941	0.5960	−0.0450	0.030*
H4B	0.1019	0.5333	−0.1400	0.030*
C5	0.10617 (4)	0.53843 (11)	0.1778 (4)	0.0252 (5)
H5	0.1199	0.5560	0.1685	0.030*
C6	0.09524 (5)	0.56653 (11)	0.3591 (5)	0.0356 (6)
H6A	0.0945	0.6110	0.3413	0.043*
H6B	0.1026	0.5579	0.4875	0.043*
C7	0.07398 (5)	0.54031 (11)	0.3735 (5)	0.0342 (6)
H7	0.0668	0.5591	0.4924	0.041*
C8	0.07510 (4)	0.47116 (10)	0.4044 (5)	0.0282 (5)
H8A	0.0614	0.4541	0.4118	0.034*
H8B	0.0820	0.4620	0.5352	0.034*
C9	0.10775 (3)	0.46982 (10)	0.2081 (4)	0.0220 (5)
H9A	0.1153	0.4610	0.3351	0.026*
H9B	0.1150	0.4516	0.0909	0.026*
C10	0.06261 (4)	0.55420 (11)	0.1747 (5)	0.0345 (6)
H10A	0.0489	0.5377	0.1834	0.041*
H10B	0.0617	0.5985	0.1550	0.041*
C11	0.08839 (3)	0.37444 (9)	0.2426 (4)	0.0199 (4)
C12	0.09709 (3)	0.28280 (10)	0.3552 (4)	0.0212 (4)
C13	0.10506 (4)	0.36501 (10)	0.5994 (4)	0.0245 (5)
H13A	0.1079	0.4084	0.5892	0.037*
H13B	0.1175	0.3432	0.6308	0.037*
H13C	0.0953	0.3580	0.7091	0.037*
C14	0.08542 (3)	0.22529 (9)	0.0446 (4)	0.0227 (5)
H14A	0.0890	0.2344	−0.0997	0.027*
H14B	0.0947	0.1934	0.0935	0.027*
C15	0.05794 (4)	0.18967 (13)	0.2540 (5)	0.0345 (6)
H15A	0.0564	0.2283	0.3293	0.041*
H15B	0.0677	0.1644	0.3292	0.041*
C16	0.03797 (4)	0.15741 (15)	0.2457 (6)	0.0427 (8)
H16A	0.0398	0.1168	0.1842	0.051*
H16B	0.0328	0.1519	0.3870	0.051*
C17	0.03096 (4)	0.20593 (11)	−0.0794 (4)	0.0278 (5)
H17A	0.0212	0.2321	−0.1518	0.033*
H17B	0.0326	0.1683	−0.1602	0.033*
C18	0.05105 (4)	0.23845 (11)	−0.0635 (4)	0.0261 (5)
H18A	0.0563	0.2468	−0.2030	0.031*
H18B	0.0492	0.2776	0.0078	0.031*
C19	0.00324 (4)	0.17111 (11)	0.1365 (4)	0.0281 (5)
C20	−0.01038 (4)	0.17995 (14)	−0.0246 (5)	0.0366 (6)
H20	−0.0061	0.1985	−0.1485	0.044*
C21	−0.03030 (4)	0.16163 (14)	−0.0037 (6)	0.0426 (7)
H21	−0.0393	0.1678	−0.1147	0.051*
C22	−0.03716 (4)	0.13510 (14)	0.1726 (6)	0.0404 (7)
H22	−0.0507	0.1227	0.1841	0.048*
C23	−0.02392 (4)	0.12670 (14)	0.3341 (6)	0.0421 (7)
H23	−0.0285	0.1087	0.4578	0.051*
C24	−0.00399 (4)	0.14421 (14)	0.3179 (5)	0.0365 (6)
H24	0.0048	0.1380	0.4304	0.044*
Cl1	0.02109 (2)	0.01531 (9)	0.0431 (3)	0.0562 (4)	0.50
Cl2	0.0020 (2)	−0.0144 (4)	−0.3345 (6)	0.143 (3)	0.50
C25	0.00259 (15)	−0.0235 (4)	−0.0659 (17)	0.073 (2)	0.50
H25A	−0.0103	−0.0100	−0.0076	0.088*	0.50
H25B	0.0042	−0.0670	−0.0331	0.088*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0326 (3)	0.0149 (2)	0.0267 (3)	0.0043 (2)	0.0009 (2)	0.0027 (2)
N1	0.0249 (9)	0.0129 (8)	0.0214 (10)	0.0011 (6)	−0.0011 (7)	−0.0014 (7)
N2	0.0278 (9)	0.0130 (8)	0.0248 (11)	−0.0014 (7)	0.0005 (8)	0.0021 (8)
N3	0.0324 (10)	0.0115 (8)	0.0218 (10)	−0.0020 (7)	0.0025 (8)	0.0002 (7)
N4	0.0244 (9)	0.0159 (8)	0.0266 (11)	−0.0011 (7)	0.0011 (8)	0.0007 (8)
N5	0.0237 (9)	0.0280 (9)	0.0252 (11)	0.0024 (8)	−0.0004 (8)	0.0046 (9)
C1	0.0202 (9)	0.0136 (9)	0.0212 (12)	0.0006 (7)	0.0027 (8)	0.0024 (8)
C2	0.0285 (11)	0.0162 (10)	0.0323 (14)	0.0006 (8)	−0.0061 (10)	0.0003 (10)
C3	0.0293 (11)	0.0166 (10)	0.0328 (14)	0.0045 (8)	−0.0026 (10)	0.0035 (10)
C4	0.0341 (12)	0.0160 (9)	0.0256 (13)	0.0007 (8)	0.0031 (10)	0.0045 (9)
C5	0.0311 (12)	0.0173 (10)	0.0274 (13)	−0.0061 (8)	−0.0017 (10)	0.0043 (9)
C6	0.0644 (18)	0.0135 (10)	0.0288 (15)	−0.0043 (10)	−0.0054 (13)	−0.0001 (10)
C7	0.0535 (16)	0.0183 (10)	0.0308 (15)	0.0140 (10)	0.0160 (12)	0.0015 (10)
C8	0.0339 (12)	0.0184 (10)	0.0323 (15)	0.0062 (9)	0.0139 (10)	0.0059 (10)
C9	0.0211 (10)	0.0189 (10)	0.0259 (14)	−0.0019 (7)	0.0023 (8)	0.0045 (9)
C10	0.0377 (13)	0.0223 (11)	0.0436 (16)	0.0123 (10)	0.0102 (12)	0.0069 (11)
C11	0.0197 (9)	0.0166 (9)	0.0234 (12)	−0.0002 (7)	0.0010 (8)	0.0011 (9)
C12	0.0250 (10)	0.0136 (9)	0.0252 (12)	−0.0006 (8)	0.0027 (9)	−0.0018 (9)
C13	0.0323 (12)	0.0175 (10)	0.0239 (12)	0.0049 (8)	−0.0056 (10)	−0.0023 (9)
C14	0.0293 (11)	0.0151 (9)	0.0239 (13)	−0.0028 (8)	0.0054 (9)	−0.0037 (9)
C15	0.0240 (11)	0.0448 (14)	0.0348 (15)	−0.0005 (10)	−0.0018 (11)	0.0222 (13)
C16	0.0234 (11)	0.0544 (17)	0.0504 (19)	−0.0021 (11)	−0.0016 (12)	0.0336 (16)
C17	0.0292 (12)	0.0297 (12)	0.0244 (12)	−0.0018 (9)	−0.0028 (9)	0.0004 (10)
C18	0.0327 (12)	0.0231 (10)	0.0224 (12)	−0.0025 (9)	−0.0018 (9)	0.0044 (9)
C19	0.0243 (11)	0.0265 (11)	0.0335 (15)	0.0049 (9)	0.0024 (10)	−0.0044 (10)
C20	0.0304 (12)	0.0439 (14)	0.0356 (17)	0.0019 (11)	−0.0042 (11)	0.0003 (13)
C21	0.0277 (12)	0.0500 (16)	0.0500 (19)	0.0048 (11)	−0.0068 (13)	−0.0122 (15)
C22	0.0241 (12)	0.0406 (15)	0.057 (2)	−0.0005 (10)	0.0028 (12)	−0.0154 (14)
C23	0.0312 (13)	0.0454 (16)	0.0498 (19)	−0.0028 (11)	0.0101 (13)	0.0008 (14)
C24	0.0279 (12)	0.0425 (15)	0.0391 (17)	−0.0006 (10)	0.0028 (11)	0.0028 (13)
Cl1	0.0308 (7)	0.0813 (11)	0.0563 (11)	0.0133 (7)	−0.0006 (6)	−0.0114 (9)
Cl2	0.150 (5)	0.182 (8)	0.096 (2)	−0.015 (6)	0.001 (3)	−0.007 (3)
C25	0.074 (5)	0.059 (4)	0.086 (6)	0.008 (4)	−0.001 (5)	−0.005 (4)

S1—C12	1.684 (2)	C8—H8A	0.9900
N1—C12	1.378 (3)	C8—H8B	0.9900
N1—C11	1.384 (3)	C9—H9A	0.9900
N1—C13	1.458 (3)	C9—H9B	0.9900
N2—C11	1.308 (3)	C10—H10A	0.9900
N2—N3	1.386 (2)	C10—H10B	0.9900
N3—C12	1.333 (3)	C13—H13A	0.9800
N3—C14	1.482 (3)	C13—H13B	0.9800
N4—C14	1.442 (3)	C13—H13C	0.9800
N4—C15	1.448 (3)	C14—H14A	0.9900
N4—C18	1.453 (3)	C14—H14B	0.9900
N5—C19	1.417 (3)	C15—C16	1.515 (3)
N5—C16	1.460 (3)	C15—H15A	0.9900
N5—C17	1.462 (3)	C15—H15B	0.9900
C1—C11	1.507 (3)	C16—H16A	0.9900
C1—C2	1.542 (3)	C16—H16B	0.9900
C1—C9	1.545 (3)	C17—C18	1.526 (3)
C1—C8	1.545 (3)	C17—H17A	0.9900
C2—C3	1.536 (3)	C17—H17B	0.9900
C2—H2A	0.9900	C18—H18A	0.9900
C2—H2B	0.9900	C18—H18B	0.9900
C3—C10	1.527 (4)	C19—C20	1.403 (4)
C3—C4	1.531 (3)	C19—C24	1.408 (4)
C3—H3	1.0000	C20—C21	1.398 (4)
C4—C5	1.538 (4)	C20—H20	0.9500
C4—H4A	0.9900	C21—C22	1.368 (5)
C4—H4B	0.9900	C21—H21	0.9500
C5—C6	1.521 (4)	C22—C23	1.386 (5)
C5—C9	1.533 (3)	C22—H22	0.9500
C5—H5	1.0000	C23—C24	1.392 (4)
C6—C7	1.538 (4)	C23—H23	0.9500
C6—H6A	0.9900	C24—H24	0.9500
C6—H6B	0.9900	Cl1—C25	1.664 (10)
C7—C10	1.532 (4)	Cl2—C25	1.761 (12)
C7—C8	1.544 (3)	C25—H25A	0.9900
C7—H7	1.0000	C25—H25B	0.9900
C12—N1—C11	107.82 (19)	C3—C10—H10B	109.8
C12—N1—C13	121.3 (2)	C7—C10—H10B	109.8
C11—N1—C13	130.84 (18)	H10A—C10—H10B	108.3
C11—N2—N3	104.64 (19)	N2—C11—N1	110.43 (18)
C12—N3—N2	112.72 (18)	N2—C11—C1	123.3 (2)
C12—N3—C14	126.35 (19)	N1—C11—C1	126.1 (2)
N2—N3—C14	120.92 (19)	N3—C12—N1	104.39 (19)
C14—N4—C15	113.7 (2)	N3—C12—S1	129.11 (17)
C14—N4—C18	113.51 (18)	N1—C12—S1	126.51 (19)
C15—N4—C18	110.06 (19)	N1—C13—H13A	109.5
C19—N5—C16	116.5 (2)	N1—C13—H13B	109.5
C19—N5—C17	116.6 (2)	H13A—C13—H13B	109.5
C16—N5—C17	111.7 (2)	N1—C13—H13C	109.5
C11—C1—C2	108.64 (18)	H13A—C13—H13C	109.5
C11—C1—C9	108.97 (17)	H13B—C13—H13C	109.5
C2—C1—C9	108.83 (19)	N4—C14—N3	115.42 (19)
C11—C1—C8	112.89 (18)	N4—C14—H14A	108.4
C2—C1—C8	107.53 (19)	N3—C14—H14A	108.4
C9—C1—C8	109.89 (19)	N4—C14—H14B	108.4
C3—C2—C1	110.5 (2)	N3—C14—H14B	108.4
C3—C2—H2A	109.5	H14A—C14—H14B	107.5
C1—C2—H2A	109.5	N4—C15—C16	110.7 (2)
C3—C2—H2B	109.5	N4—C15—H15A	109.5
C1—C2—H2B	109.5	C16—C15—H15A	109.5
H2A—C2—H2B	108.1	N4—C15—H15B	109.5
C10—C3—C4	109.9 (2)	C16—C15—H15B	109.5
C10—C3—C2	109.5 (2)	H15A—C15—H15B	108.1
C4—C3—C2	109.13 (18)	N5—C16—C15	111.7 (2)
C10—C3—H3	109.4	N5—C16—H16A	109.3
C4—C3—H3	109.4	C15—C16—H16A	109.3
C2—C3—H3	109.4	N5—C16—H16B	109.3
C3—C4—C5	109.2 (2)	C15—C16—H16B	109.3
C3—C4—H4A	109.8	H16A—C16—H16B	107.9
C5—C4—H4A	109.8	N5—C17—C18	110.5 (2)
C3—C4—H4B	109.8	N5—C17—H17A	109.6
C5—C4—H4B	109.8	C18—C17—H17A	109.6
H4A—C4—H4B	108.3	N5—C17—H17B	109.6
C6—C5—C9	109.7 (2)	C18—C17—H17B	109.6
C6—C5—C4	109.9 (2)	H17A—C17—H17B	108.1
C9—C5—C4	109.4 (2)	N4—C18—C17	110.37 (19)
C6—C5—H5	109.3	N4—C18—H18A	109.6
C9—C5—H5	109.3	C17—C18—H18A	109.6
C4—C5—H5	109.3	N4—C18—H18B	109.6
C5—C6—C7	109.7 (2)	C17—C18—H18B	109.6
C5—C6—H6A	109.7	H18A—C18—H18B	108.1
C7—C6—H6A	109.7	C20—C19—C24	117.6 (2)
C5—C6—H6B	109.7	C20—C19—N5	122.2 (3)
C7—C6—H6B	109.7	C24—C19—N5	120.1 (2)
H6A—C6—H6B	108.2	C21—C20—C19	120.3 (3)
C10—C7—C6	109.4 (2)	C21—C20—H20	119.8
C10—C7—C8	109.4 (2)	C19—C20—H20	119.8
C6—C7—C8	109.7 (2)	C22—C21—C20	121.7 (3)
C10—C7—H7	109.5	C22—C21—H21	119.2
C6—C7—H7	109.5	C20—C21—H21	119.2
C8—C7—H7	109.5	C21—C22—C23	118.7 (3)
C7—C8—C1	109.6 (2)	C21—C22—H22	120.7
C7—C8—H8A	109.8	C23—C22—H22	120.7
C1—C8—H8A	109.8	C22—C23—C24	121.1 (3)
C7—C8—H8B	109.8	C22—C23—H23	119.5
C1—C8—H8B	109.8	C24—C23—H23	119.5
H8A—C8—H8B	108.2	C23—C24—C19	120.6 (3)
C5—C9—C1	109.71 (18)	C23—C24—H24	119.7
C5—C9—H9A	109.7	C19—C24—H24	119.7
C1—C9—H9A	109.7	Cl1—C25—Cl2	112.3 (8)
C5—C9—H9B	109.7	Cl1—C25—H25A	109.1
C1—C9—H9B	109.7	Cl2—C25—H25A	109.1
H9A—C9—H9B	108.2	Cl1—C25—H25B	109.1
C3—C10—C7	109.3 (2)	Cl2—C25—H25B	109.1
C3—C10—H10A	109.8	H25A—C25—H25B	107.9
C7—C10—H10A	109.8
C11—N2—N3—C12	0.2 (2)	C2—C1—C11—N1	−176.7 (2)
C11—N2—N3—C14	−179.6 (2)	C9—C1—C11—N1	64.9 (3)
C11—C1—C2—C3	−177.29 (19)	C8—C1—C11—N1	−57.5 (3)
C9—C1—C2—C3	−58.8 (2)	N2—N3—C12—N1	−0.1 (2)
C8—C1—C2—C3	60.2 (2)	N2—N3—C12—S1	−179.48 (17)
C1—C2—C3—C10	−60.5 (3)	C14—N3—C12—S1	0.3 (3)
C1—C2—C3—C4	59.9 (3)	C11—N1—C12—N3	0.0 (2)
C10—C3—C4—C5	59.7 (2)	C13—N1—C12—N3	−179.56 (19)
C2—C3—C4—C5	−60.5 (3)	C11—N1—C12—S1	179.40 (17)
C3—C4—C5—C6	−59.3 (2)	C13—N1—C12—S1	−0.2 (3)
C3—C4—C5—C9	61.3 (2)	C15—N4—C14—N3	−54.9 (3)
C9—C5—C6—C7	−60.9 (3)	C18—N4—C14—N3	71.9 (3)
C4—C5—C6—C7	59.5 (3)	C12—N3—C14—N4	100.3 (3)
C5—C6—C7—C10	−59.8 (3)	N2—N3—C14—N4	−79.9 (3)
C5—C6—C7—C8	60.2 (3)	C14—N4—C15—C16	−172.6 (2)
C10—C7—C8—C1	61.3 (3)	C18—N4—C15—C16	58.8 (3)
C6—C7—C8—C1	−58.6 (3)	C19—N5—C16—C15	−169.1 (3)
C11—C1—C8—C7	179.8 (2)	C17—N5—C16—C15	53.3 (3)
C2—C1—C8—C7	−60.4 (3)	N4—C15—C16—N5	−55.6 (3)
C9—C1—C8—C7	57.9 (3)	C19—N5—C17—C18	168.7 (2)
C6—C5—C9—C1	60.0 (3)	C16—N5—C17—C18	−53.8 (3)
C4—C5—C9—C1	−60.6 (3)	C14—N4—C18—C17	171.5 (2)
C11—C1—C9—C5	177.2 (2)	C15—N4—C18—C17	−59.8 (3)
C2—C1—C9—C5	58.9 (2)	N5—C17—C18—N4	57.1 (3)
C8—C1—C9—C5	−58.6 (3)	C16—N5—C19—C20	−152.3 (3)
C4—C3—C10—C7	−60.4 (3)	C17—N5—C19—C20	−16.8 (3)
C2—C3—C10—C7	59.5 (3)	C16—N5—C19—C24	31.2 (4)
C6—C7—C10—C3	59.9 (3)	C17—N5—C19—C24	166.7 (2)
C8—C7—C10—C3	−60.2 (3)	C24—C19—C20—C21	−0.9 (4)
N3—N2—C11—N1	−0.1 (2)	N5—C19—C20—C21	−177.4 (2)
N3—N2—C11—C1	175.2 (2)	C19—C20—C21—C22	0.4 (5)
C12—N1—C11—N2	0.1 (3)	C20—C21—C22—C23	0.4 (5)
C12—N1—C11—C1	−175.1 (2)	C21—C22—C23—C24	−0.6 (5)
C13—N1—C11—C1	4.4 (4)	C22—C23—C24—C19	0.1 (5)
C2—C1—C11—N2	8.7 (3)	C20—C19—C24—C23	0.6 (4)
C9—C1—C11—N2	−109.8 (2)	N5—C19—C24—C23	177.2 (3)
C8—C1—C11—N2	127.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···S1i	0.99	2.85	3.803 (3)	162
C16—H16A···Cl1	0.99	2.73	3.589 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯S1i	0.99	2.85	3.803 (3)	162
C16—H16A⋯Cl1	0.99	2.73	3.589 (4)	146

Symmetry code: (i) .