2-Phenyl-5,6,7,8-tetra-hydro-imidazo[2,1-b][1,3]benzo-thia-zole.

The title compound, C15H14N2S, crystallizes with two independent mol-ecules in the asymmetric unit. The central imidazo[2,1-b][1,3]benzo-thia-zole unit is planar (r.m.s. deviations of 0.010 and 0.008 Å for the two independent mol-ecules). The fused tetra-hydro-hexane ring adopts a half-chair conformation. The phenyl substituent is twisted by 16.96 (13) and 22.89 (12)° relative to the central imidazo[2,1-b][1,3]benzo-thia-zole unit in the two mol-ecules. In the crystal, there are no significant intermolecular interactions present.

Related literature

For applications of imidazo[2,1-b][1,3]benzo­thia­zoles, see: Ager et al. (1988 ▶); Sanfilippo et al. (1988 ▶); Barchéchath et al. (2005 ▶); Andreani et al. (2008 ▶); Chao et al. (2009 ▶); Kumbhare et al. (2011 ▶); Chandak et al. (2013 ▶). For the crystal structures of related compounds, see: Landreau et al. (2002 ▶); Adib et al. (2008 ▶); Fun, Asik et al. (2011 ▶); Fun, Hemamalini et al. (2011 ▶); Ghabbour et al. (2012 ▶); Bunev et al. (2013a ▶,b ▶, 2014 ▶).

Experimental

Crystal data

C15H14N2S

M = 254.34

Monoclinic,

a = 12.523 (3) Å

b = 10.699 (3) Å

c = 18.930 (5) Å

β = 102.291 (6)°

V = 2478.2 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 120 K

0.30 × 0.05 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.931, T max = 0.993

33479 measured reflections

7558 independent reflections

3223 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.157

S = 0.93

7558 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814010885/rk2428sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010885/rk2428Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010885/rk2428Isup3.cml

CCDC reference: 1002491

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

C15H14N2S	F(000) = 1072
Mr = 254.34	Dx = 1.363 Mg m−3
Monoclinic, P21/n	Melting point = 440–442 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.523 (3) Å	Cell parameters from 769 reflections
b = 10.699 (3) Å	θ = 2.2–19.4°
c = 18.930 (5) Å	µ = 0.24 mm−1
β = 102.291 (6)°	T = 120 K
V = 2478.2 (11) Å3	Needle, colourless
Z = 8	0.30 × 0.05 × 0.03 mm

Bruker APEXII CCD diffractometer	7558 independent reflections
Radiation source: fine-focus sealed tube	3223 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
φ and ω scans	θmax = 30.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −17→17
Tmin = 0.931, Tmax = 0.993	k = −15→15
33479 measured reflections	l = −27→27

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0349P)2] where P = (Fo2 + 2Fc2)/3
7558 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.3882 (2)	0.6184 (2)	0.11553 (14)	0.0237 (6)
C2	0.3823 (3)	0.5036 (3)	0.14946 (16)	0.0212 (7)
C3	0.4704 (3)	0.4301 (3)	0.14592 (16)	0.0219 (7)
H3	0.4850	0.3481	0.1647	0.026*
N4	0.5337 (2)	0.5003 (2)	0.10923 (14)	0.0205 (6)
C4A	0.6340 (3)	0.4902 (3)	0.08809 (16)	0.0209 (7)
C5	0.7062 (2)	0.3795 (3)	0.10652 (18)	0.0248 (7)
H5A	0.6796	0.3105	0.0725	0.030*
H5B	0.7049	0.3508	0.1560	0.030*
C6	0.8230 (3)	0.4141 (3)	0.10196 (18)	0.0277 (8)
H6A	0.8567	0.4646	0.1447	0.033*
H6B	0.8668	0.3370	0.1024	0.033*
C7	0.8246 (3)	0.4884 (3)	0.03323 (17)	0.0254 (7)
H7A	0.7920	0.4368	−0.0093	0.030*
H7B	0.9014	0.5058	0.0309	0.030*
C8	0.7619 (3)	0.6131 (3)	0.02925 (17)	0.0255 (7)
H8A	0.8072	0.6760	0.0605	0.031*
H8B	0.7463	0.6448	−0.0210	0.031*
C8A	0.6568 (2)	0.5938 (3)	0.05377 (16)	0.0212 (7)
S9	0.55424 (7)	0.70942 (8)	0.04714 (5)	0.0253 (2)
C9A	0.4804 (3)	0.6118 (3)	0.09283 (16)	0.0213 (7)
C10	0.2878 (3)	0.4714 (3)	0.18064 (17)	0.0229 (7)
C11	0.2908 (3)	0.3708 (3)	0.22804 (17)	0.0250 (7)
H11	0.3563	0.3241	0.2426	0.030*
C12	0.1987 (3)	0.3383 (3)	0.25409 (17)	0.0292 (8)
H12	0.2018	0.2695	0.2862	0.035*
C13	0.1024 (3)	0.4053 (3)	0.23360 (18)	0.0297 (8)
H13	0.0393	0.3822	0.2509	0.036*
C14	0.0992 (3)	0.5066 (3)	0.18754 (18)	0.0297 (8)
H14	0.0339	0.5539	0.1737	0.036*
C15	0.1911 (3)	0.5393 (3)	0.16149 (17)	0.0267 (8)
H15	0.1879	0.6091	0.1301	0.032*
N16	−0.1213 (2)	0.9124 (2)	0.11849 (14)	0.0252 (6)
C17	−0.1096 (3)	1.0225 (3)	0.15894 (17)	0.0224 (7)
C18	−0.0110 (3)	1.0785 (3)	0.15889 (16)	0.0230 (7)
H18	0.0156	1.1548	0.1818	0.028*
N19	0.0414 (2)	1.0016 (2)	0.11889 (14)	0.0218 (6)
C19A	0.1393 (3)	0.9974 (3)	0.09439 (17)	0.0230 (7)
C20	0.2241 (3)	1.0980 (3)	0.11148 (17)	0.0260 (8)
H20A	0.2640	1.0906	0.1624	0.031*
H20B	0.1887	1.1811	0.1049	0.031*
C21	0.3034 (3)	1.0841 (3)	0.06097 (18)	0.0278 (8)
H21A	0.3690	1.1358	0.0793	0.033*
H21B	0.2683	1.1156	0.0124	0.033*
C22	0.3384 (3)	0.9486 (3)	0.05454 (18)	0.0282 (8)
H22A	0.3731	0.9166	0.1031	0.034*
H22B	0.3934	0.9450	0.0239	0.034*
C23	0.2406 (3)	0.8651 (3)	0.02141 (17)	0.0252 (8)
H23A	0.2206	0.8784	−0.0315	0.030*
H23B	0.2608	0.7761	0.0304	0.030*
C23A	0.1451 (3)	0.8957 (3)	0.05424 (17)	0.0252 (7)
S24	0.02778 (7)	0.79992 (8)	0.04362 (5)	0.0269 (2)
C24A	−0.0288 (3)	0.9037 (3)	0.09640 (16)	0.0218 (7)
C25	−0.1985 (3)	1.0704 (3)	0.19086 (17)	0.0247 (7)
C26	−0.1767 (3)	1.1565 (3)	0.24797 (17)	0.0266 (8)
H26	−0.1036	1.1819	0.2669	0.032*
C27	−0.2608 (3)	1.2052 (3)	0.27725 (17)	0.0284 (8)
H27	−0.2448	1.2638	0.3158	0.034*
C28	−0.3676 (3)	1.1686 (3)	0.25042 (18)	0.0309 (8)
H28	−0.4250	1.2023	0.2704	0.037*
C29	−0.3911 (3)	1.0825 (3)	0.19427 (19)	0.0320 (8)
H29	−0.4645	1.0571	0.1760	0.038*
C30	−0.3071 (3)	1.0334 (3)	0.16478 (18)	0.0288 (8)
H30	−0.3236	0.9742	0.1266	0.035*

	U11	U22	U33	U12	U13	U23
N1	0.0236 (16)	0.0247 (16)	0.0223 (15)	0.0008 (12)	0.0038 (12)	0.0008 (11)
C2	0.0226 (18)	0.0226 (18)	0.0176 (16)	−0.0013 (13)	0.0027 (13)	−0.0033 (13)
C3	0.0264 (19)	0.0189 (17)	0.0217 (17)	0.0003 (13)	0.0082 (14)	0.0012 (13)
N4	0.0203 (15)	0.0194 (14)	0.0222 (15)	0.0007 (11)	0.0056 (11)	−0.0013 (11)
C4A	0.0207 (18)	0.0205 (17)	0.0207 (17)	0.0004 (13)	0.0025 (13)	−0.0032 (13)
C5	0.0242 (19)	0.0234 (18)	0.0280 (19)	0.0038 (14)	0.0087 (14)	0.0019 (14)
C6	0.0255 (19)	0.0277 (19)	0.0293 (19)	0.0043 (15)	0.0041 (15)	0.0022 (15)
C7	0.0232 (18)	0.0280 (19)	0.0267 (19)	−0.0010 (14)	0.0093 (14)	−0.0037 (14)
C8	0.0258 (19)	0.0275 (19)	0.0237 (18)	−0.0024 (14)	0.0065 (14)	0.0008 (14)
C8A	0.0233 (18)	0.0203 (17)	0.0194 (17)	−0.0003 (13)	0.0031 (13)	−0.0019 (13)
S9	0.0254 (5)	0.0210 (4)	0.0300 (5)	0.0024 (4)	0.0073 (4)	0.0033 (4)
C9A	0.0233 (18)	0.0189 (17)	0.0208 (17)	0.0013 (13)	0.0025 (13)	−0.0038 (13)
C10	0.0221 (18)	0.0250 (18)	0.0218 (17)	−0.0025 (13)	0.0053 (14)	−0.0044 (13)
C11	0.0261 (19)	0.0234 (18)	0.0262 (19)	0.0019 (14)	0.0071 (14)	−0.0031 (14)
C12	0.038 (2)	0.0266 (19)	0.0237 (19)	−0.0050 (15)	0.0087 (16)	−0.0005 (14)
C13	0.027 (2)	0.033 (2)	0.031 (2)	−0.0085 (16)	0.0101 (15)	−0.0087 (16)
C14	0.0192 (18)	0.040 (2)	0.029 (2)	0.0017 (15)	0.0030 (15)	−0.0046 (16)
C15	0.0261 (19)	0.033 (2)	0.0224 (18)	−0.0005 (15)	0.0074 (14)	−0.0006 (14)
N16	0.0287 (17)	0.0234 (15)	0.0229 (15)	−0.0014 (12)	0.0040 (12)	0.0014 (12)
C17	0.0249 (19)	0.0205 (17)	0.0209 (17)	0.0003 (13)	0.0032 (14)	0.0006 (13)
C18	0.0278 (19)	0.0188 (17)	0.0220 (18)	0.0022 (14)	0.0038 (14)	−0.0012 (13)
N19	0.0238 (15)	0.0209 (14)	0.0201 (15)	−0.0018 (11)	0.0035 (11)	−0.0012 (11)
C19A	0.0231 (18)	0.0224 (18)	0.0224 (18)	0.0016 (14)	0.0026 (14)	0.0025 (13)
C20	0.0263 (19)	0.0229 (18)	0.0274 (19)	−0.0010 (14)	0.0024 (14)	−0.0018 (14)
C21	0.027 (2)	0.0255 (19)	0.030 (2)	−0.0035 (15)	0.0035 (15)	−0.0016 (15)
C22	0.030 (2)	0.029 (2)	0.0267 (19)	0.0067 (15)	0.0085 (15)	0.0044 (14)
C23	0.031 (2)	0.0228 (18)	0.0215 (18)	0.0062 (14)	0.0054 (15)	0.0026 (13)
C23A	0.029 (2)	0.0241 (19)	0.0217 (18)	0.0014 (14)	0.0037 (14)	0.0059 (14)
S24	0.0317 (5)	0.0198 (4)	0.0286 (5)	−0.0002 (4)	0.0051 (4)	−0.0023 (4)
C24A	0.0260 (19)	0.0176 (17)	0.0213 (17)	−0.0016 (13)	0.0037 (14)	0.0000 (13)
C25	0.028 (2)	0.0225 (18)	0.0238 (18)	0.0006 (14)	0.0050 (14)	0.0070 (14)
C26	0.027 (2)	0.030 (2)	0.0217 (18)	−0.0011 (14)	0.0031 (14)	0.0086 (14)
C27	0.036 (2)	0.0271 (19)	0.0227 (18)	0.0041 (16)	0.0075 (15)	0.0067 (15)
C28	0.033 (2)	0.031 (2)	0.032 (2)	0.0081 (16)	0.0136 (16)	0.0109 (15)
C29	0.024 (2)	0.032 (2)	0.039 (2)	−0.0034 (15)	0.0054 (16)	0.0086 (17)
C30	0.029 (2)	0.030 (2)	0.0269 (19)	−0.0025 (15)	0.0032 (15)	0.0002 (14)

N1—C9A	1.317 (4)	N16—C24A	1.316 (4)
N1—C2	1.395 (4)	N16—C17	1.395 (4)
C2—C3	1.368 (4)	C17—C18	1.373 (4)
C2—C10	1.472 (4)	C17—C25	1.468 (4)
C3—N4	1.382 (4)	C18—N19	1.376 (4)
C3—H3	0.9500	C18—H18	0.9500
N4—C9A	1.370 (4)	N19—C24A	1.376 (4)
N4—C4A	1.400 (4)	N19—C19A	1.400 (4)
C4A—C8A	1.346 (4)	C19A—C23A	1.338 (4)
C4A—C5	1.486 (4)	C19A—C20	1.498 (4)
C5—C6	1.529 (4)	C20—C21	1.526 (4)
C5—H5A	0.9900	C20—H20A	0.9900
C5—H5B	0.9900	C20—H20B	0.9900
C6—C7	1.528 (4)	C21—C22	1.527 (4)
C6—H6A	0.9900	C21—H21A	0.9900
C6—H6B	0.9900	C21—H21B	0.9900
C7—C8	1.542 (4)	C22—C23	1.538 (4)
C7—H7A	0.9900	C22—H22A	0.9900
C7—H7B	0.9900	C22—H22B	0.9900
C8—C8A	1.500 (4)	C23—C23A	1.497 (4)
C8—H8A	0.9900	C23—H23A	0.9900
C8—H8B	0.9900	C23—H23B	0.9900
C8A—S9	1.769 (3)	C23A—S24	1.767 (3)
S9—C9A	1.742 (3)	S24—C24A	1.742 (3)
C10—C15	1.392 (4)	C25—C30	1.401 (4)
C10—C11	1.397 (4)	C25—C26	1.402 (4)
C11—C12	1.392 (4)	C26—C27	1.392 (4)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.385 (5)	C27—C28	1.382 (5)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.386 (5)	C28—C29	1.390 (5)
C13—H13	0.9500	C28—H28	0.9500
C14—C15	1.390 (4)	C29—C30	1.395 (5)
C14—H14	0.9500	C29—H29	0.9500
C15—H15	0.9500	C30—H30	0.9500
C9A—N1—C2	103.8 (3)	C24A—N16—C17	103.7 (3)
C3—C2—N1	111.2 (3)	C18—C17—N16	111.0 (3)
C3—C2—C10	127.7 (3)	C18—C17—C25	127.6 (3)
N1—C2—C10	121.1 (3)	N16—C17—C25	121.3 (3)
C2—C3—N4	105.5 (3)	C17—C18—N19	105.9 (3)
C2—C3—H3	127.2	C17—C18—H18	127.1
N4—C3—H3	127.2	N19—C18—H18	127.1
C9A—N4—C3	106.4 (3)	C18—N19—C24A	106.1 (3)
C9A—N4—C4A	115.2 (3)	C18—N19—C19A	139.1 (3)
C3—N4—C4A	138.3 (3)	C24A—N19—C19A	114.8 (3)
C8A—C4A—N4	111.7 (3)	C23A—C19A—N19	111.8 (3)
C8A—C4A—C5	126.0 (3)	C23A—C19A—C20	125.8 (3)
N4—C4A—C5	122.2 (3)	N19—C19A—C20	122.4 (3)
C4A—C5—C6	109.6 (3)	C19A—C20—C21	108.7 (3)
C4A—C5—H5A	109.7	C19A—C20—H20A	109.9
C6—C5—H5A	109.7	C21—C20—H20A	109.9
C4A—C5—H5B	109.7	C19A—C20—H20B	109.9
C6—C5—H5B	109.7	C21—C20—H20B	109.9
H5A—C5—H5B	108.2	H20A—C20—H20B	108.3
C7—C6—C5	111.1 (3)	C20—C21—C22	112.2 (3)
C7—C6—H6A	109.4	C20—C21—H21A	109.2
C5—C6—H6A	109.4	C22—C21—H21A	109.2
C7—C6—H6B	109.4	C20—C21—H21B	109.2
C5—C6—H6B	109.4	C22—C21—H21B	109.2
H6A—C6—H6B	108.0	H21A—C21—H21B	107.9
C6—C7—C8	113.1 (3)	C21—C22—C23	111.5 (3)
C6—C7—H7A	109.0	C21—C22—H22A	109.3
C8—C7—H7A	109.0	C23—C22—H22A	109.3
C6—C7—H7B	109.0	C21—C22—H22B	109.3
C8—C7—H7B	109.0	C23—C22—H22B	109.3
H7A—C7—H7B	107.8	H22A—C22—H22B	108.0
C8A—C8—C7	109.7 (3)	C23A—C23—C22	109.9 (3)
C8A—C8—H8A	109.7	C23A—C23—H23A	109.7
C7—C8—H8A	109.7	C22—C23—H23A	109.7
C8A—C8—H8B	109.7	C23A—C23—H23B	109.7
C7—C8—H8B	109.7	C22—C23—H23B	109.7
H8A—C8—H8B	108.2	H23A—C23—H23B	108.2
C4A—C8A—C8	123.6 (3)	C19A—C23A—C23	124.0 (3)
C4A—C8A—S9	112.6 (2)	C19A—C23A—S24	113.1 (3)
C8—C8A—S9	123.6 (2)	C23—C23A—S24	123.0 (2)
C9A—S9—C8A	89.97 (15)	C24A—S24—C23A	89.70 (15)
N1—C9A—N4	113.1 (3)	N16—C24A—N19	113.3 (3)
N1—C9A—S9	136.4 (3)	N16—C24A—S24	136.1 (3)
N4—C9A—S9	110.5 (2)	N19—C24A—S24	110.6 (2)
C15—C10—C11	118.2 (3)	C30—C25—C26	118.2 (3)
C15—C10—C2	120.2 (3)	C30—C25—C17	121.4 (3)
C11—C10—C2	121.6 (3)	C26—C25—C17	120.4 (3)
C12—C11—C10	120.6 (3)	C27—C26—C25	120.9 (3)
C12—C11—H11	119.7	C27—C26—H26	119.6
C10—C11—H11	119.7	C25—C26—H26	119.6
C13—C12—C11	120.6 (3)	C28—C27—C26	120.2 (3)
C13—C12—H12	119.7	C28—C27—H27	119.9
C11—C12—H12	119.7	C26—C27—H27	119.9
C12—C13—C14	119.2 (3)	C27—C28—C29	120.0 (3)
C12—C13—H13	120.4	C27—C28—H28	120.0
C14—C13—H13	120.4	C29—C28—H28	120.0
C13—C14—C15	120.4 (3)	C28—C29—C30	120.1 (3)
C13—C14—H14	119.8	C28—C29—H29	120.0
C15—C14—H14	119.8	C30—C29—H29	120.0
C14—C15—C10	121.1 (3)	C29—C30—C25	120.7 (3)
C14—C15—H15	119.5	C29—C30—H30	119.6
C10—C15—H15	119.5	C25—C30—H30	119.6
C9A—N1—C2—C3	−0.5 (3)	C24A—N16—C17—C18	1.2 (4)
C9A—N1—C2—C10	−177.9 (3)	C24A—N16—C17—C25	177.0 (3)
N1—C2—C3—N4	0.3 (4)	N16—C17—C18—N19	−1.1 (4)
C10—C2—C3—N4	177.5 (3)	C25—C17—C18—N19	−176.5 (3)
C2—C3—N4—C9A	0.0 (3)	C17—C18—N19—C24A	0.5 (3)
C2—C3—N4—C4A	177.0 (3)	C17—C18—N19—C19A	178.2 (3)
C9A—N4—C4A—C8A	−1.3 (4)	C18—N19—C19A—C23A	−178.6 (3)
C3—N4—C4A—C8A	−178.1 (3)	C24A—N19—C19A—C23A	−1.0 (4)
C9A—N4—C4A—C5	175.3 (3)	C18—N19—C19A—C20	0.5 (6)
C3—N4—C4A—C5	−1.5 (6)	C24A—N19—C19A—C20	178.1 (3)
C8A—C4A—C5—C6	17.0 (4)	C23A—C19A—C20—C21	14.3 (4)
N4—C4A—C5—C6	−159.1 (3)	N19—C19A—C20—C21	−164.7 (3)
C4A—C5—C6—C7	−45.4 (4)	C19A—C20—C21—C22	−45.1 (4)
C5—C6—C7—C8	61.3 (4)	C20—C21—C22—C23	62.7 (4)
C6—C7—C8—C8A	−42.5 (4)	C21—C22—C23—C23A	−43.5 (4)
N4—C4A—C8A—C8	175.9 (3)	N19—C19A—C23A—C23	−179.2 (3)
C5—C4A—C8A—C8	−0.6 (5)	C20—C19A—C23A—C23	1.7 (5)
N4—C4A—C8A—S9	0.6 (3)	N19—C19A—C23A—S24	0.8 (4)
C5—C4A—C8A—S9	−175.9 (3)	C20—C19A—C23A—S24	−178.3 (2)
C7—C8—C8A—C4A	12.9 (4)	C22—C23—C23A—C19A	13.0 (4)
C7—C8—C8A—S9	−172.2 (2)	C22—C23—C23A—S24	−167.0 (2)
C4A—C8A—S9—C9A	0.2 (3)	C19A—C23A—S24—C24A	−0.3 (3)
C8—C8A—S9—C9A	−175.1 (3)	C23—C23A—S24—C24A	179.7 (3)
C2—N1—C9A—N4	0.6 (3)	C17—N16—C24A—N19	−0.9 (3)
C2—N1—C9A—S9	−178.9 (3)	C17—N16—C24A—S24	−179.3 (3)
C3—N4—C9A—N1	−0.4 (4)	C18—N19—C24A—N16	0.3 (4)
C4A—N4—C9A—N1	−178.2 (3)	C19A—N19—C24A—N16	−178.0 (3)
C3—N4—C9A—S9	179.2 (2)	C18—N19—C24A—S24	179.1 (2)
C4A—N4—C9A—S9	1.5 (3)	C19A—N19—C24A—S24	0.8 (3)
C8A—S9—C9A—N1	178.6 (4)	C23A—S24—C24A—N16	178.2 (4)
C8A—S9—C9A—N4	−0.9 (2)	C23A—S24—C24A—N19	−0.3 (2)
C3—C2—C10—C15	−160.7 (3)	C18—C17—C25—C30	154.6 (3)
N1—C2—C10—C15	16.3 (5)	N16—C17—C25—C30	−20.4 (5)
C3—C2—C10—C11	17.3 (5)	C18—C17—C25—C26	−24.4 (5)
N1—C2—C10—C11	−165.7 (3)	N16—C17—C25—C26	160.6 (3)
C15—C10—C11—C12	1.2 (5)	C30—C25—C26—C27	−0.9 (5)
C2—C10—C11—C12	−176.8 (3)	C17—C25—C26—C27	178.1 (3)
C10—C11—C12—C13	−0.1 (5)	C25—C26—C27—C28	0.3 (5)
C11—C12—C13—C14	−0.9 (5)	C26—C27—C28—C29	0.3 (5)
C12—C13—C14—C15	0.9 (5)	C27—C28—C29—C30	−0.3 (5)
C13—C14—C15—C10	0.2 (5)	C28—C29—C30—C25	−0.3 (5)
C11—C10—C15—C14	−1.2 (5)	C26—C25—C30—C29	0.9 (5)
C2—C10—C15—C14	176.8 (3)	C17—C25—C30—C29	−178.1 (3)