Crystal structure of bis-[μ-S-hexyl 3-(2-oxido-benzyl-idene)di-thio-carbazato-κ(4) O,N (3),S:O]dicopper(II).

The title compound, [Cu2(C14H18N2OS2)2], is a binuclear copper(II) complex of an oxybenzyl-idenedi-thio-carbazate ligand. The ligand coordinates in a tridentate manner through N-, S- and O-donor atoms. Each O atom also bridges to a second Cu(II) ion to form the binuclear species. It has a central Cu2O2 rhomboid moiety and a metal-to-metal separation of 2.9923 (6) Å. In the crystal, the binuclear complexes stack along the a axis with all the hexyl chains located side-by-side, forming a hydro-phobic region. The complexes are linked via C-H⋯N hydrogen bonds, forming chains along the c-axis direction. One Cu(II) atom has the S atom of a symmetry-related complex located approximately in the apical position at 2.9740 (11) Å. This weak inter-action links the chains to form slabs parallel to the ac plane.

Related literature

For details of the bioactivities of metal complexes of bidentate Schiff bases of S-methyl or S-benzyl di­thio­carbazate ligands, see: Chan et al. (2008 ▸); How et al. (2008 ▸); Ali et al. (2002 ▸); Chew et al. (2004 ▸). For square-planar metal complexes of di­thio­carbazate ligands coordinating in a bidentate manner, see: Tarafder et al. (2008 ▸); Howlader et al. (2015 ▸); Begum et al. (2015 ▸). For Cu—N and Cu—S bond lengths in mononuclear bis-chelated species, see: Zangrando, Begum et al. (2015 ▸); Zangrando, Islam et al. (2015 ▸). For copper(II) complexes of similar ligands, see: Ali, Tan et al. (2012 ▸); Ali, Mirza et al. (2012 ▸).

Experimental

Crystal data

[Cu2(C14H18N2OS2)2]

M = 715.93

Monoclinic,

a = 7.2792 (4) Å

b = 37.7252 (16) Å

c = 11.3443 (5) Å

β = 94.701 (2)°

V = 3104.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.67 mm−1

T = 173 K

0.36 × 0.34 × 0.03 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▸) T min = 0.723, T max = 0.951

12702 measured reflections

5278 independent reflections

5114 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.066

S = 1.06

5278 reflections

361 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack x determined using 2223 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.006 (6)

Data collection: RAPID-AUTO (Rigaku, 2001 ▸); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: CrystalStructure (Rigaku, 2010 ▸); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015022914/su5246sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022914/su5246Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015022914/su5246fig1.tif

A view of the mol­ecular structure of the title complex, with atom labelling. The displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

c i x y z . DOI: 10.1107/S2056989015022914/su5246fig2.tif

A view along the c axis of the crystal packing of the title complex. Dotted lines indicated the Cu2—S2i distances of 2.9740 (11) Å [symmetry code: (i) x − , −y + , z + ], and H atoms have been omitted for clarity.

CCDC reference: 1439650

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

[Cu2(C14H18N2OS2)2]	F(000) = 1480
Mr = 715.93	Dx = 1.532 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71075 Å
a = 7.2792 (4) Å	Cell parameters from 701 reflections
b = 37.7252 (16) Å	θ = 3.2–26.4°
c = 11.3443 (5) Å	µ = 1.67 mm−1
β = 94.701 (2)°	T = 173 K
V = 3104.8 (3) Å3	Platelet, brown
Z = 4	0.36 × 0.34 × 0.03 mm

Rigaku R-AXIS RAPID diffractometer	5114 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1	Rint = 0.025
ω scans	θmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.723, Tmax = 0.951	k = −45→45
12702 measured reflections	l = −13→13
5278 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(Fo2) + (0.0398P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.066	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.60 e Å−3
5278 reflections	Δρmin = −0.29 e Å−3
361 parameters	Absolute structure: Flack x determined using 2223 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.006 (6)

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Cu1	0.15703 (6)	0.75915 (2)	0.15440 (4)	0.02305 (13)
Cu2	0.17703 (6)	0.81382 (2)	0.34616 (4)	0.02522 (13)
S1	0.26421 (15)	0.70459 (3)	0.13607 (8)	0.0267 (2)
S2	0.29460 (14)	0.66844 (3)	−0.10024 (8)	0.0271 (2)
S3	0.29144 (15)	0.86872 (3)	0.36366 (9)	0.0318 (2)
S4	0.39250 (16)	0.90558 (3)	0.58598 (10)	0.0330 (2)
O1	0.1071 (4)	0.80939 (7)	0.1742 (2)	0.0258 (7)
O2	0.1407 (4)	0.76259 (7)	0.3249 (2)	0.0257 (7)
N1	0.1368 (5)	0.76188 (8)	−0.0151 (3)	0.0235 (8)
N2	0.1776 (5)	0.73220 (9)	−0.0820 (3)	0.0255 (7)
N3	0.2447 (5)	0.80819 (9)	0.5132 (3)	0.0252 (8)
N4	0.3081 (5)	0.83759 (9)	0.5811 (3)	0.0282 (7)
C1	0.0484 (6)	0.83258 (10)	0.0903 (4)	0.0249 (8)
C2	−0.0068 (6)	0.86690 (10)	0.1209 (4)	0.0298 (9)
H2	−0.0044	0.8733	0.2020	0.036*
C3	−0.0638 (6)	0.89129 (10)	0.0367 (4)	0.0328 (9)
H3	−0.0995	0.9143	0.0602	0.039*
C4	−0.0704 (6)	0.88291 (11)	−0.0835 (4)	0.0347 (10)
H4	−0.1093	0.9000	−0.1417	0.042*
C5	−0.0199 (6)	0.84966 (11)	−0.1157 (4)	0.0296 (9)
H5	−0.0246	0.8438	−0.1974	0.036*
C6	0.0393 (6)	0.82360 (11)	−0.0312 (3)	0.0252 (8)
C7	0.0854 (6)	0.78960 (10)	−0.0771 (3)	0.0252 (9)
H7	0.0776	0.7871	−0.1607	0.030*
C8	0.2370 (5)	0.70578 (10)	−0.0176 (3)	0.0221 (8)
C9	0.3329 (6)	0.63379 (10)	0.0105 (4)	0.0285 (9)
H9A	0.4534	0.6375	0.0559	0.034*
H9B	0.2355	0.6349	0.0665	0.034*
C10	0.3300 (7)	0.59759 (10)	−0.0491 (4)	0.0332 (9)
H10A	0.4213	0.5971	−0.1091	0.040*
H10B	0.2065	0.5932	−0.0899	0.040*
C11	0.3752 (7)	0.56854 (11)	0.0424 (4)	0.0384 (10)
H11A	0.5040	0.5716	0.0761	0.046*
H11B	0.2939	0.5713	0.1076	0.046*
C12	0.3525 (8)	0.53115 (12)	−0.0078 (5)	0.0502 (13)
H12A	0.3759	0.5140	0.0576	0.060*
H12B	0.2230	0.5280	−0.0403	0.060*
C13	0.4783 (9)	0.52245 (13)	−0.1038 (6)	0.0617 (16)
H13A	0.6074	0.5273	−0.0739	0.074*
H13B	0.4477	0.5381	−0.1726	0.074*
C14	0.4620 (10)	0.48402 (14)	−0.1440 (7)	0.075 (2)
H14A	0.5457	0.4797	−0.2058	0.113*
H14B	0.4947	0.4683	−0.0766	0.113*
H14C	0.3349	0.4792	−0.1753	0.113*
C15	0.1172 (6)	0.73824 (10)	0.4088 (3)	0.0234 (8)
C16	0.0434 (6)	0.70501 (11)	0.3792 (4)	0.0266 (8)
H16	0.0100	0.6996	0.2985	0.032*
C17	0.0179 (6)	0.67982 (11)	0.4649 (3)	0.0283 (9)
H17	−0.0324	0.6573	0.4423	0.034*
C18	0.0653 (7)	0.68710 (11)	0.5843 (4)	0.0333 (10)
H18	0.0492	0.6696	0.6430	0.040*
C19	0.1349 (6)	0.71952 (10)	0.6152 (3)	0.0292 (9)
H19	0.1661	0.7246	0.6964	0.035*
C20	0.1624 (6)	0.74617 (10)	0.5296 (4)	0.0266 (8)
C21	0.2290 (6)	0.77955 (11)	0.5743 (3)	0.0272 (9)
H21	0.2651	0.7809	0.6566	0.033*
C22	0.3282 (6)	0.86546 (11)	0.5167 (4)	0.0282 (9)
C23	0.4128 (7)	0.89347 (12)	0.7416 (4)	0.0357 (10)
H23A	0.3009	0.8806	0.7615	0.043*
H23B	0.5205	0.8777	0.7587	0.043*
C24	0.4365 (7)	0.92718 (12)	0.8150 (4)	0.0399 (11)
H24A	0.5535	0.9388	0.7985	0.048*
H24B	0.3345	0.9437	0.7913	0.048*
C25	0.4385 (7)	0.91990 (12)	0.9463 (4)	0.0394 (11)
H25A	0.3241	0.9071	0.9614	0.047*
H25B	0.5437	0.9041	0.9698	0.047*
C26	0.4533 (9)	0.95249 (13)	1.0232 (5)	0.0572 (15)
H26A	0.3523	0.9690	0.9970	0.069*
H26B	0.5714	0.9646	1.0120	0.069*
C27	0.4440 (12)	0.94475 (19)	1.1539 (5)	0.076 (2)
H27A	0.3329	0.9302	1.1634	0.091*
H27B	0.5527	0.9303	1.1814	0.091*
C28	0.4381 (15)	0.9760 (2)	1.2308 (7)	0.112 (3)
H28A	0.4322	0.9683	1.3130	0.168*
H28B	0.5492	0.9903	1.2245	0.168*
H28C	0.3288	0.9902	1.2064	0.168*

	U11	U22	U33	U12	U13	U23
Cu1	0.0294 (3)	0.0239 (2)	0.0163 (2)	0.00168 (19)	0.00456 (18)	−0.00053 (18)
Cu2	0.0311 (3)	0.0258 (2)	0.0191 (2)	−0.0010 (2)	0.00362 (19)	−0.00153 (18)
S1	0.0357 (6)	0.0258 (5)	0.0190 (4)	0.0041 (4)	0.0043 (4)	−0.0001 (4)
S2	0.0330 (5)	0.0255 (5)	0.0233 (5)	0.0004 (4)	0.0064 (4)	−0.0035 (4)
S3	0.0355 (6)	0.0315 (5)	0.0288 (5)	−0.0062 (4)	0.0043 (4)	0.0002 (4)
S4	0.0333 (6)	0.0303 (5)	0.0352 (5)	−0.0036 (4)	0.0025 (4)	−0.0060 (4)
O1	0.0368 (18)	0.0231 (13)	0.0182 (14)	0.0014 (11)	0.0060 (13)	−0.0001 (10)
O2	0.0404 (19)	0.0221 (13)	0.0152 (13)	0.0010 (12)	0.0062 (13)	0.0000 (10)
N1	0.0246 (18)	0.0249 (17)	0.0211 (17)	0.0009 (14)	0.0033 (14)	−0.0018 (13)
N2	0.0339 (19)	0.0258 (17)	0.0175 (16)	0.0003 (15)	0.0058 (14)	−0.0034 (13)
N3	0.0249 (19)	0.0290 (17)	0.0217 (17)	0.0006 (14)	0.0025 (14)	−0.0062 (14)
N4	0.0288 (18)	0.0293 (17)	0.0262 (17)	0.0000 (15)	0.0004 (15)	−0.0040 (14)
C1	0.022 (2)	0.030 (2)	0.0228 (18)	−0.0012 (16)	0.0031 (15)	0.0006 (16)
C2	0.032 (2)	0.030 (2)	0.029 (2)	0.0007 (17)	0.0068 (18)	−0.0032 (16)
C3	0.035 (2)	0.026 (2)	0.038 (2)	0.0032 (18)	0.0027 (19)	−0.0031 (18)
C4	0.037 (2)	0.031 (2)	0.035 (2)	0.0037 (19)	−0.0043 (19)	0.0069 (18)
C5	0.034 (2)	0.030 (2)	0.0239 (19)	−0.0007 (17)	−0.0023 (17)	0.0022 (17)
C6	0.023 (2)	0.031 (2)	0.0218 (19)	−0.0015 (17)	0.0021 (16)	0.0003 (16)
C7	0.024 (2)	0.032 (2)	0.0196 (18)	−0.0026 (17)	0.0035 (16)	−0.0001 (16)
C8	0.0188 (19)	0.0265 (19)	0.0219 (19)	−0.0012 (15)	0.0067 (15)	−0.0016 (15)
C9	0.030 (2)	0.027 (2)	0.030 (2)	−0.0011 (17)	0.0087 (17)	0.0014 (17)
C10	0.038 (2)	0.024 (2)	0.039 (2)	−0.0020 (17)	0.0107 (19)	−0.0021 (17)
C11	0.038 (3)	0.031 (2)	0.047 (3)	0.0040 (19)	0.004 (2)	0.005 (2)
C12	0.048 (3)	0.030 (2)	0.072 (3)	−0.001 (2)	0.006 (3)	0.010 (2)
C13	0.062 (4)	0.038 (3)	0.088 (4)	0.001 (3)	0.022 (3)	−0.010 (3)
C14	0.077 (5)	0.040 (3)	0.110 (6)	0.004 (3)	0.006 (4)	−0.022 (3)
C15	0.023 (2)	0.025 (2)	0.0232 (19)	0.0055 (15)	0.0076 (16)	0.0023 (15)
C16	0.028 (2)	0.031 (2)	0.0214 (18)	0.0040 (17)	0.0047 (16)	−0.0016 (16)
C17	0.030 (2)	0.027 (2)	0.028 (2)	0.0006 (17)	0.0053 (17)	0.0007 (16)
C18	0.039 (3)	0.034 (2)	0.028 (2)	0.0077 (19)	0.0099 (19)	0.0101 (17)
C19	0.034 (2)	0.035 (2)	0.0196 (18)	0.0064 (18)	0.0042 (16)	0.0023 (16)
C20	0.028 (2)	0.032 (2)	0.0205 (19)	0.0081 (17)	0.0069 (16)	−0.0001 (16)
C21	0.026 (2)	0.038 (2)	0.0183 (18)	0.0055 (18)	0.0022 (16)	0.0006 (17)
C22	0.020 (2)	0.034 (2)	0.031 (2)	−0.0013 (16)	0.0036 (17)	−0.0095 (18)
C23	0.039 (3)	0.034 (2)	0.033 (2)	−0.006 (2)	0.002 (2)	−0.0093 (19)
C24	0.047 (3)	0.034 (2)	0.038 (2)	−0.002 (2)	0.004 (2)	−0.010 (2)
C25	0.040 (3)	0.037 (2)	0.041 (2)	−0.003 (2)	0.008 (2)	−0.011 (2)
C26	0.083 (4)	0.040 (3)	0.048 (3)	0.006 (3)	−0.001 (3)	−0.015 (2)
C27	0.103 (6)	0.078 (4)	0.047 (3)	0.005 (4)	0.008 (4)	−0.016 (3)
C28	0.134 (8)	0.128 (7)	0.074 (5)	0.005 (6)	0.017 (5)	−0.048 (5)

Cu1—N1	1.919 (4)	C11—H11A	0.9900
Cu1—O1	1.946 (3)	C11—H11B	0.9900
Cu1—O2	1.952 (3)	C12—C13	1.515 (8)
Cu1—S1	2.2171 (10)	C12—H12A	0.9900
Cu1—Cu2	2.9923 (6)	C12—H12B	0.9900
Cu2—N3	1.931 (4)	C13—C14	1.522 (7)
Cu2—O2	1.963 (2)	C13—H13A	0.9900
Cu2—O1	1.982 (3)	C13—H13B	0.9900
Cu2—S3	2.2352 (11)	C14—H14A	0.9800
S1—C8	1.739 (4)	C14—H14B	0.9800
S2—C8	1.762 (4)	C14—H14C	0.9800
S2—C9	1.819 (4)	C15—C16	1.394 (6)
S3—C22	1.739 (4)	C15—C20	1.415 (6)
S4—C22	1.751 (4)	C16—C17	1.383 (6)
S4—C23	1.817 (4)	C16—H16	0.9500
O1—C1	1.337 (5)	C17—C18	1.398 (6)
O2—C15	1.343 (5)	C17—H17	0.9500
N1—C7	1.299 (5)	C18—C19	1.359 (6)
N1—N2	1.399 (5)	C18—H18	0.9500
N2—C8	1.289 (5)	C19—C20	1.423 (6)
N3—C21	1.293 (5)	C19—H19	0.9500
N3—N4	1.406 (5)	C20—C21	1.428 (6)
N4—C22	1.295 (5)	C21—H21	0.9500
C1—C2	1.407 (6)	C23—C24	1.522 (6)
C1—C6	1.416 (5)	C23—H23A	0.9900
C2—C3	1.366 (6)	C23—H23B	0.9900
C2—H2	0.9500	C24—C25	1.513 (6)
C3—C4	1.396 (6)	C24—H24A	0.9900
C3—H3	0.9500	C24—H24B	0.9900
C4—C5	1.366 (6)	C25—C26	1.507 (6)
C4—H4	0.9500	C25—H25A	0.9900
C5—C6	1.415 (6)	C25—H25B	0.9900
C5—H5	0.9500	C26—C27	1.517 (8)
C6—C7	1.434 (6)	C26—H26A	0.9900
C7—H7	0.9500	C26—H26B	0.9900
C9—C10	1.524 (5)	C27—C28	1.468 (9)
C9—H9A	0.9900	C27—H27A	0.9900
C9—H9B	0.9900	C27—H27B	0.9900
C10—C11	1.527 (6)	C28—H28A	0.9800
C10—H10A	0.9900	C28—H28B	0.9800
C10—H10B	0.9900	C28—H28C	0.9800
C11—C12	1.525 (6)
N1—Cu1—O1	93.65 (12)	H11A—C11—H11B	107.7
N1—Cu1—O2	169.54 (14)	C13—C12—C11	114.5 (4)
O1—Cu1—O2	78.10 (11)	C13—C12—H12A	108.6
N1—Cu1—S1	87.40 (10)	C11—C12—H12A	108.6
O1—Cu1—S1	170.18 (10)	C13—C12—H12B	108.6
O2—Cu1—S1	101.83 (8)	C11—C12—H12B	108.6
N1—Cu1—Cu2	133.36 (9)	H12A—C12—H12B	107.6
O1—Cu1—Cu2	40.83 (8)	C12—C13—C14	112.6 (5)
O2—Cu1—Cu2	40.28 (7)	C12—C13—H13A	109.1
S1—Cu1—Cu2	135.36 (3)	C14—C13—H13A	109.1
N3—Cu2—O2	91.89 (13)	C12—C13—H13B	109.1
N3—Cu2—O1	168.85 (12)	C14—C13—H13B	109.1
O2—Cu2—O1	77.02 (11)	H13A—C13—H13B	107.8
N3—Cu2—S3	87.22 (11)	C13—C14—H14A	109.5
O2—Cu2—S3	165.65 (10)	C13—C14—H14B	109.5
O1—Cu2—S3	103.25 (9)	H14A—C14—H14B	109.5
N3—Cu2—Cu1	129.13 (10)	C13—C14—H14C	109.5
O2—Cu2—Cu1	40.03 (8)	H14A—C14—H14C	109.5
O1—Cu2—Cu1	39.94 (8)	H14B—C14—H14C	109.5
S3—Cu2—Cu1	134.33 (3)	O2—C15—C16	120.9 (3)
C8—S1—Cu1	93.33 (13)	O2—C15—C20	120.6 (3)
C8—S2—C9	103.67 (19)	C16—C15—C20	118.5 (4)
C22—S3—Cu2	92.80 (14)	C17—C16—C15	121.3 (4)
C22—S4—C23	102.5 (2)	C17—C16—H16	119.3
C1—O1—Cu1	127.4 (3)	C15—C16—H16	119.3
C1—O1—Cu2	133.4 (2)	C16—C17—C18	120.6 (4)
Cu1—O1—Cu2	99.23 (12)	C16—C17—H17	119.7
C15—O2—Cu1	132.7 (2)	C18—C17—H17	119.7
C15—O2—Cu2	127.6 (2)	C19—C18—C17	119.0 (4)
Cu1—O2—Cu2	99.69 (12)	C19—C18—H18	120.5
C7—N1—N2	114.5 (3)	C17—C18—H18	120.5
C7—N1—Cu1	125.6 (3)	C18—C19—C20	122.0 (4)
N2—N1—Cu1	119.9 (2)	C18—C19—H19	119.0
C8—N2—N1	112.8 (3)	C20—C19—H19	119.0
C21—N3—N4	113.9 (3)	C15—C20—C19	118.5 (4)
C21—N3—Cu2	126.2 (3)	C15—C20—C21	125.1 (4)
N4—N3—Cu2	119.8 (3)	C19—C20—C21	116.3 (4)
C22—N4—N3	112.2 (3)	N3—C21—C20	126.1 (4)
O1—C1—C2	120.5 (4)	N3—C21—H21	117.0
O1—C1—C6	121.6 (4)	C20—C21—H21	117.0
C2—C1—C6	117.9 (4)	N4—C22—S3	127.2 (3)
C3—C2—C1	121.6 (4)	N4—C22—S4	119.1 (3)
C3—C2—H2	119.2	S3—C22—S4	113.6 (2)
C1—C2—H2	119.2	C24—C23—S4	108.5 (3)
C2—C3—C4	121.0 (4)	C24—C23—H23A	110.0
C2—C3—H3	119.5	S4—C23—H23A	110.0
C4—C3—H3	119.5	C24—C23—H23B	110.0
C5—C4—C3	118.8 (4)	S4—C23—H23B	110.0
C5—C4—H4	120.6	H23A—C23—H23B	108.4
C3—C4—H4	120.6	C25—C24—C23	112.2 (4)
C4—C5—C6	122.0 (4)	C25—C24—H24A	109.2
C4—C5—H5	119.0	C23—C24—H24A	109.2
C6—C5—H5	119.0	C25—C24—H24B	109.2
C5—C6—C1	118.7 (4)	C23—C24—H24B	109.2
C5—C6—C7	116.3 (4)	H24A—C24—H24B	107.9
C1—C6—C7	125.0 (4)	C26—C25—C24	114.6 (4)
N1—C7—C6	126.1 (4)	C26—C25—H25A	108.6
N1—C7—H7	117.0	C24—C25—H25A	108.6
C6—C7—H7	117.0	C26—C25—H25B	108.6
N2—C8—S1	126.4 (3)	C24—C25—H25B	108.6
N2—C8—S2	113.6 (3)	H25A—C25—H25B	107.6
S1—C8—S2	120.0 (2)	C25—C26—C27	113.7 (5)
C10—C9—S2	110.0 (3)	C25—C26—H26A	108.8
C10—C9—H9A	109.7	C27—C26—H26A	108.8
S2—C9—H9A	109.7	C25—C26—H26B	108.8
C10—C9—H9B	109.7	C27—C26—H26B	108.8
S2—C9—H9B	109.7	H26A—C26—H26B	107.7
H9A—C9—H9B	108.2	C28—C27—C26	115.6 (6)
C9—C10—C11	110.3 (4)	C28—C27—H27A	108.4
C9—C10—H10A	109.6	C26—C27—H27A	108.4
C11—C10—H10A	109.6	C28—C27—H27B	108.4
C9—C10—H10B	109.6	C26—C27—H27B	108.4
C11—C10—H10B	109.6	H27A—C27—H27B	107.4
H10A—C10—H10B	108.1	C27—C28—H28A	109.5
C12—C11—C10	113.5 (4)	C27—C28—H28B	109.5
C12—C11—H11A	108.9	H28A—C28—H28B	109.5
C10—C11—H11A	108.9	C27—C28—H28C	109.5
C12—C11—H11B	108.9	H28A—C28—H28C	109.5
C10—C11—H11B	108.9	H28B—C28—H28C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N2i	0.95	2.52	3.457 (5)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯N2i	0.95	2.52	3.457 (5)	167

Symmetry code: (i) .