rac-3-{4-[(4-Nitro-benzyl-idene)amino]-3-phenyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenyl-propan-1-one.

In the title mol-ecule, C(30)H(23)N(5)O(3)S, the 1,2,4-triazole ring is approximately planar (r.m.s. deviation = 0.006 Å), and forms dihedral angles of 66.0 (2), 65.1 (2), 30.1 (2) and 28.1 (2)° with the four phenyl rings. The phenyl ring of the benzyl group directly attached to the triazole ring is almost perpendicular to the nitro-phenyl ring, making a dihedral angle of 84.9 (2)°.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C30H23N5O3S

M = 533.59

Monoclinic,

a = 13.3303 (13) Å

b = 21.832 (2) Å

c = 9.2773 (9) Å

β = 98.213 (3)°

V = 2672.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.968, T max = 0.981

27241 measured reflections

6372 independent reflections

5124 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.131

S = 1.10

6372 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035197/zs2140sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035197/zs2140Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035197/zs2140Isup3.cml

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

C30H23N5O3S	F(000) = 1112
Mr = 533.59	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8592 reflections
a = 13.3303 (13) Å	θ = 1.5–27.9°
b = 21.832 (2) Å	µ = 0.16 mm−1
c = 9.2773 (9) Å	T = 113 K
β = 98.213 (3)°	Prism, colorless
V = 2672.2 (4) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	6372 independent reflections
Radiation source: rotating anode	5124 reflections with I > 2σ(I)
multilayer	Rint = 0.040
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.5°
φ and ω scans	h = −15→17
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −27→28
Tmin = 0.968, Tmax = 0.981	l = −12→12
27241 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.1147P] where P = (Fo2 + 2Fc2)/3
6372 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.33 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	0.40778 (3)	0.258871 (19)	0.46718 (5)	0.03324 (14)
O1	0.33880 (9)	0.08657 (5)	0.76721 (14)	0.0346 (3)
O2	−0.05157 (12)	0.41949 (7)	−0.22517 (19)	0.0649 (5)
O3	−0.07948 (10)	0.33342 (7)	−0.34027 (17)	0.0545 (4)
N1	0.41855 (9)	0.13669 (6)	0.49993 (14)	0.0250 (3)
N2	0.37677 (10)	0.08227 (6)	0.44644 (15)	0.0273 (3)
N3	0.30586 (9)	0.16063 (6)	0.32011 (14)	0.0265 (3)
N4	0.23159 (10)	0.18795 (7)	0.22006 (15)	0.0305 (3)
N5	−0.03993 (11)	0.36460 (8)	−0.23724 (19)	0.0440 (4)
C1	0.37777 (12)	0.18629 (7)	0.42770 (17)	0.0258 (3)
C2	0.30761 (12)	0.09772 (7)	0.33837 (18)	0.0268 (4)
C3	0.49357 (11)	0.13916 (7)	0.63312 (17)	0.0244 (3)
H3	0.4677	0.1679	0.7033	0.029*
C4	0.50513 (11)	0.07593 (7)	0.70349 (17)	0.0252 (3)
H4A	0.5231	0.0462	0.6307	0.030*
H4B	0.5621	0.0772	0.7846	0.030*
C5	0.41174 (12)	0.05325 (7)	0.76135 (17)	0.0255 (3)
C6	0.41222 (11)	−0.01130 (7)	0.81389 (16)	0.0246 (3)
C7	0.50162 (12)	−0.04455 (7)	0.84342 (17)	0.0264 (3)
H7	0.5640	−0.0265	0.8279	0.032*
C8	0.50025 (13)	−0.10395 (7)	0.89538 (18)	0.0306 (4)
H8	0.5617	−0.1265	0.9151	0.037*
C9	0.40986 (13)	−0.13060 (8)	0.91858 (19)	0.0332 (4)
H9	0.4091	−0.1715	0.9534	0.040*
C10	0.32011 (14)	−0.09748 (8)	0.89083 (19)	0.0342 (4)
H10	0.2580	−0.1155	0.9079	0.041*
C11	0.32128 (12)	−0.03833 (8)	0.83847 (18)	0.0305 (4)
H11	0.2598	−0.0159	0.8190	0.037*
C12	0.59542 (11)	0.16257 (7)	0.60266 (17)	0.0244 (3)
C13	0.64074 (12)	0.14022 (8)	0.48742 (18)	0.0305 (4)
H13	0.6057	0.1114	0.4219	0.037*
C14	0.73711 (13)	0.15985 (8)	0.4674 (2)	0.0363 (4)
H14	0.7679	0.1442	0.3888	0.044*
C15	0.78809 (13)	0.20224 (8)	0.5621 (2)	0.0358 (4)
H15	0.8536	0.2160	0.5482	0.043*
C16	0.74310 (13)	0.22440 (8)	0.67691 (19)	0.0335 (4)
H16	0.7783	0.2532	0.7424	0.040*
C17	0.64733 (12)	0.20516 (7)	0.69740 (18)	0.0291 (4)
H17	0.6169	0.2210	0.7761	0.035*
C18	0.23453 (13)	0.24544 (9)	0.1994 (2)	0.0375 (4)
H18	0.2862	0.2696	0.2532	0.045*
C19	0.15729 (12)	0.27428 (9)	0.0914 (2)	0.0363 (4)
C20	0.09104 (13)	0.24006 (8)	−0.0091 (2)	0.0359 (4)
H20	0.0912	0.1966	−0.0037	0.043*
C21	0.02564 (13)	0.26954 (9)	−0.1159 (2)	0.0368 (4)
H21	−0.0185	0.2469	−0.1858	0.044*
C22	0.02605 (12)	0.33251 (8)	−0.1185 (2)	0.0356 (4)
C23	0.08666 (13)	0.36786 (9)	−0.0181 (2)	0.0427 (5)
H23	0.0828	0.4113	−0.0206	0.051*
C24	0.15371 (13)	0.33767 (9)	0.0872 (2)	0.0422 (5)
H24	0.1974	0.3608	0.1568	0.051*
C25	0.24185 (12)	0.05265 (8)	0.25380 (19)	0.0321 (4)
C26	0.22312 (14)	−0.00168 (8)	0.3235 (2)	0.0435 (5)
H26	0.2505	−0.0077	0.4227	0.052*
C27	0.16458 (16)	−0.04698 (9)	0.2484 (3)	0.0564 (6)
H27	0.1526	−0.0843	0.2959	0.068*
C28	0.12366 (15)	−0.03807 (10)	0.1051 (3)	0.0564 (6)
H28	0.0829	−0.0691	0.0544	0.068*
C29	0.14132 (14)	0.01515 (10)	0.0354 (2)	0.0497 (6)
H29	0.1124	0.0210	−0.0633	0.060*
C30	0.20157 (13)	0.06087 (9)	0.1082 (2)	0.0394 (5)
H30	0.2151	0.0974	0.0589	0.047*

	U11	U22	U33	U12	U13	U23
S1	0.0366 (3)	0.0258 (2)	0.0356 (3)	0.00011 (17)	−0.00091 (18)	0.00255 (18)
O1	0.0319 (6)	0.0328 (6)	0.0388 (7)	0.0046 (5)	0.0042 (5)	0.0019 (5)
O2	0.0617 (10)	0.0478 (9)	0.0783 (12)	0.0076 (8)	−0.0139 (8)	0.0202 (8)
O3	0.0449 (8)	0.0643 (10)	0.0487 (9)	0.0034 (7)	−0.0129 (7)	0.0094 (7)
N1	0.0259 (7)	0.0233 (7)	0.0240 (7)	0.0000 (5)	−0.0030 (5)	−0.0019 (5)
N2	0.0260 (7)	0.0266 (7)	0.0273 (7)	−0.0003 (5)	−0.0034 (5)	−0.0049 (6)
N3	0.0228 (7)	0.0326 (8)	0.0226 (7)	0.0029 (5)	−0.0017 (5)	0.0005 (6)
N4	0.0257 (7)	0.0405 (8)	0.0237 (7)	0.0052 (6)	−0.0020 (5)	0.0046 (6)
N5	0.0315 (8)	0.0484 (10)	0.0501 (11)	0.0016 (7)	−0.0006 (7)	0.0160 (8)
C1	0.0236 (8)	0.0310 (9)	0.0221 (8)	0.0022 (6)	0.0015 (6)	0.0023 (6)
C2	0.0232 (8)	0.0315 (9)	0.0251 (8)	0.0021 (6)	0.0010 (6)	−0.0042 (7)
C3	0.0258 (8)	0.0240 (8)	0.0217 (8)	−0.0005 (6)	−0.0020 (6)	−0.0011 (6)
C4	0.0259 (8)	0.0253 (8)	0.0230 (8)	−0.0001 (6)	−0.0017 (6)	0.0005 (6)
C5	0.0275 (8)	0.0259 (8)	0.0213 (8)	0.0014 (6)	−0.0027 (6)	−0.0023 (6)
C6	0.0281 (8)	0.0258 (8)	0.0191 (8)	−0.0018 (6)	0.0009 (6)	−0.0032 (6)
C7	0.0287 (8)	0.0267 (8)	0.0232 (8)	−0.0023 (6)	0.0018 (6)	−0.0020 (6)
C8	0.0348 (9)	0.0290 (8)	0.0274 (9)	0.0017 (7)	0.0026 (7)	−0.0002 (7)
C9	0.0447 (10)	0.0267 (8)	0.0278 (9)	−0.0052 (7)	0.0041 (7)	0.0005 (7)
C10	0.0352 (9)	0.0357 (9)	0.0321 (10)	−0.0100 (7)	0.0055 (7)	−0.0012 (8)
C11	0.0273 (8)	0.0347 (9)	0.0288 (9)	−0.0013 (7)	0.0019 (7)	−0.0030 (7)
C12	0.0269 (8)	0.0221 (8)	0.0225 (8)	0.0005 (6)	−0.0026 (6)	0.0025 (6)
C13	0.0334 (9)	0.0311 (9)	0.0255 (9)	−0.0055 (7)	−0.0004 (7)	−0.0050 (7)
C14	0.0378 (10)	0.0422 (10)	0.0298 (9)	−0.0041 (8)	0.0085 (7)	−0.0060 (8)
C15	0.0314 (9)	0.0401 (10)	0.0359 (10)	−0.0073 (8)	0.0049 (7)	0.0011 (8)
C16	0.0332 (9)	0.0298 (9)	0.0360 (10)	−0.0072 (7)	−0.0003 (7)	−0.0045 (7)
C17	0.0316 (9)	0.0283 (8)	0.0268 (8)	−0.0016 (7)	0.0015 (7)	−0.0048 (7)
C18	0.0290 (9)	0.0465 (11)	0.0358 (10)	0.0001 (8)	0.0003 (7)	0.0075 (8)
C19	0.0250 (9)	0.0456 (11)	0.0376 (10)	0.0017 (7)	0.0023 (7)	0.0116 (8)
C20	0.0309 (9)	0.0395 (10)	0.0368 (10)	0.0007 (7)	0.0029 (7)	0.0073 (8)
C21	0.0254 (9)	0.0463 (11)	0.0384 (10)	0.0004 (8)	0.0034 (7)	0.0045 (8)
C22	0.0217 (8)	0.0459 (11)	0.0384 (10)	0.0008 (7)	0.0014 (7)	0.0124 (8)
C23	0.0324 (10)	0.0420 (11)	0.0523 (12)	−0.0025 (8)	0.0010 (8)	0.0139 (9)
C24	0.0327 (10)	0.0443 (11)	0.0464 (12)	−0.0056 (8)	−0.0054 (8)	0.0087 (9)
C25	0.0236 (8)	0.0375 (10)	0.0331 (9)	0.0050 (7)	−0.0031 (7)	−0.0122 (8)
C26	0.0400 (11)	0.0356 (10)	0.0498 (12)	0.0003 (8)	−0.0109 (9)	−0.0092 (9)
C27	0.0500 (13)	0.0375 (11)	0.0750 (16)	−0.0032 (9)	−0.0141 (11)	−0.0136 (11)
C28	0.0390 (11)	0.0530 (13)	0.0705 (16)	0.0023 (10)	−0.0148 (10)	−0.0310 (12)
C29	0.0320 (10)	0.0686 (15)	0.0441 (12)	0.0096 (10)	−0.0092 (8)	−0.0259 (11)
C30	0.0292 (9)	0.0521 (11)	0.0348 (10)	0.0064 (8)	−0.0034 (7)	−0.0142 (9)

S1—C1	1.6622 (16)	C12—C17	1.394 (2)
O1—C5	1.2218 (18)	C13—C14	1.392 (2)
O2—N5	1.215 (2)	C13—H13	0.9500
O3—N5	1.229 (2)	C14—C15	1.386 (2)
N1—C1	1.3466 (19)	C14—H14	0.9500
N1—N2	1.3745 (17)	C15—C16	1.382 (2)
N1—C3	1.4754 (18)	C15—H15	0.9500
N2—C2	1.3058 (19)	C16—C17	1.383 (2)
N3—C2	1.383 (2)	C16—H16	0.9500
N3—N4	1.3911 (17)	C17—H17	0.9500
N3—C1	1.3984 (19)	C18—C19	1.471 (2)
N4—C18	1.271 (2)	C18—H18	0.9500
N5—C22	1.483 (2)	C19—C24	1.385 (3)
C2—C25	1.468 (2)	C19—C20	1.405 (2)
C3—C12	1.515 (2)	C20—C21	1.382 (2)
C3—C4	1.525 (2)	C20—H20	0.9500
C3—H3	1.0000	C21—C22	1.375 (2)
C4—C5	1.508 (2)	C21—H21	0.9500
C4—H4A	0.9900	C22—C23	1.379 (3)
C4—H4B	0.9900	C23—C24	1.392 (2)
C5—C6	1.491 (2)	C23—H23	0.9500
C6—C7	1.389 (2)	C24—H24	0.9500
C6—C11	1.396 (2)	C25—C26	1.390 (3)
C7—C8	1.385 (2)	C25—C30	1.392 (2)
C7—H7	0.9500	C26—C27	1.384 (3)
C8—C9	1.382 (2)	C26—H26	0.9500
C8—H8	0.9500	C27—C28	1.377 (3)
C9—C10	1.390 (2)	C27—H27	0.9500
C9—H9	0.9500	C28—C29	1.367 (3)
C10—C11	1.381 (2)	C28—H28	0.9500
C10—H10	0.9500	C29—C30	1.394 (3)
C11—H11	0.9500	C29—H29	0.9500
C12—C13	1.389 (2)	C30—H30	0.9500
C1—N1—N2	113.68 (12)	C12—C13—H13	119.8
C1—N1—C3	124.37 (13)	C14—C13—H13	119.8
N2—N1—C3	121.68 (12)	C15—C14—C13	119.95 (16)
C2—N2—N1	105.02 (12)	C15—C14—H14	120.0
C2—N3—N4	120.35 (12)	C13—C14—H14	120.0
C2—N3—C1	108.21 (12)	C16—C15—C14	119.68 (16)
N4—N3—C1	130.87 (13)	C16—C15—H15	120.2
C18—N4—N3	119.33 (14)	C14—C15—H15	120.2
O2—N5—O3	124.84 (16)	C15—C16—C17	120.68 (15)
O2—N5—C22	117.86 (17)	C15—C16—H16	119.7
O3—N5—C22	117.30 (15)	C17—C16—H16	119.7
N1—C1—N3	102.69 (13)	C16—C17—C12	120.07 (16)
N1—C1—S1	126.13 (12)	C16—C17—H17	120.0
N3—C1—S1	131.16 (12)	C12—C17—H17	120.0
N2—C2—N3	110.38 (13)	N4—C18—C19	119.45 (16)
N2—C2—C25	122.63 (15)	N4—C18—H18	120.3
N3—C2—C25	126.98 (14)	C19—C18—H18	120.3
N1—C3—C12	111.99 (12)	C24—C19—C20	119.79 (16)
N1—C3—C4	109.89 (12)	C24—C19—C18	117.69 (16)
C12—C3—C4	110.29 (12)	C20—C19—C18	122.47 (17)
N1—C3—H3	108.2	C21—C20—C19	120.06 (17)
C12—C3—H3	108.2	C21—C20—H20	120.0
C4—C3—H3	108.2	C19—C20—H20	120.0
C5—C4—C3	114.30 (13)	C22—C21—C20	118.34 (17)
C5—C4—H4A	108.7	C22—C21—H21	120.8
C3—C4—H4A	108.7	C20—C21—H21	120.8
C5—C4—H4B	108.7	C21—C22—C23	123.43 (16)
C3—C4—H4B	108.7	C21—C22—N5	118.82 (16)
H4A—C4—H4B	107.6	C23—C22—N5	117.74 (16)
O1—C5—C6	120.97 (15)	C22—C23—C24	117.70 (18)
O1—C5—C4	121.53 (14)	C22—C23—H23	121.2
C6—C5—C4	117.49 (13)	C24—C23—H23	121.2
C7—C6—C11	119.18 (15)	C19—C24—C23	120.59 (17)
C7—C6—C5	121.46 (14)	C19—C24—H24	119.7
C11—C6—C5	119.33 (14)	C23—C24—H24	119.7
C8—C7—C6	120.30 (15)	C26—C25—C30	119.43 (16)
C8—C7—H7	119.8	C26—C25—C2	117.15 (16)
C6—C7—H7	119.8	C30—C25—C2	123.37 (17)
C9—C8—C7	120.23 (16)	C27—C26—C25	120.1 (2)
C9—C8—H8	119.9	C27—C26—H26	120.0
C7—C8—H8	119.9	C25—C26—H26	120.0
C8—C9—C10	119.91 (16)	C28—C27—C26	120.1 (2)
C8—C9—H9	120.0	C28—C27—H27	119.9
C10—C9—H9	120.0	C26—C27—H27	119.9
C11—C10—C9	119.93 (16)	C29—C28—C27	120.39 (19)
C11—C10—H10	120.0	C29—C28—H28	119.8
C9—C10—H10	120.0	C27—C28—H28	119.8
C10—C11—C6	120.44 (16)	C28—C29—C30	120.36 (19)
C10—C11—H11	119.8	C28—C29—H29	119.8
C6—C11—H11	119.8	C30—C29—H29	119.8
C13—C12—C17	119.23 (15)	C25—C30—C29	119.60 (19)
C13—C12—C3	121.66 (13)	C25—C30—H30	120.2
C17—C12—C3	119.01 (14)	C29—C30—H30	120.2
C12—C13—C14	120.38 (15)
C1—N1—N2—C2	−0.32 (18)	N1—C3—C12—C17	136.38 (14)
C3—N1—N2—C2	173.93 (14)	C4—C3—C12—C17	−100.89 (16)
C2—N3—N4—C18	−176.27 (16)	C17—C12—C13—C14	0.4 (2)
C1—N3—N4—C18	13.5 (3)	C3—C12—C13—C14	−176.07 (15)
N2—N1—C1—N3	−0.65 (17)	C12—C13—C14—C15	−0.4 (3)
C3—N1—C1—N3	−174.72 (13)	C13—C14—C15—C16	0.5 (3)
N2—N1—C1—S1	177.81 (12)	C14—C15—C16—C17	−0.6 (3)
C3—N1—C1—S1	3.7 (2)	C15—C16—C17—C12	0.6 (2)
C2—N3—C1—N1	1.33 (17)	C13—C12—C17—C16	−0.5 (2)
N4—N3—C1—N1	172.49 (15)	C3—C12—C17—C16	176.08 (14)
C2—N3—C1—S1	−177.02 (14)	N3—N4—C18—C19	178.74 (15)
N4—N3—C1—S1	−5.9 (3)	N4—C18—C19—C24	170.56 (18)
N1—N2—C2—N3	1.19 (18)	N4—C18—C19—C20	−11.9 (3)
N1—N2—C2—C25	−177.76 (15)	C24—C19—C20—C21	2.9 (3)
N4—N3—C2—N2	−173.91 (13)	C18—C19—C20—C21	−174.62 (17)
C1—N3—C2—N2	−1.65 (19)	C19—C20—C21—C22	−1.3 (3)
N4—N3—C2—C25	5.0 (2)	C20—C21—C22—C23	−1.6 (3)
C1—N3—C2—C25	177.24 (16)	C20—C21—C22—N5	176.85 (16)
C1—N1—C3—C12	−69.61 (19)	O2—N5—C22—C21	168.08 (18)
N2—N1—C3—C12	116.77 (15)	O3—N5—C22—C21	−11.4 (3)
C1—N1—C3—C4	167.44 (14)	O2—N5—C22—C23	−13.4 (3)
N2—N1—C3—C4	−6.2 (2)	O3—N5—C22—C23	167.13 (17)
N1—C3—C4—C5	−65.96 (17)	C21—C22—C23—C24	2.8 (3)
C12—C3—C4—C5	170.10 (12)	N5—C22—C23—C24	−175.60 (17)
C3—C4—C5—O1	−8.9 (2)	C20—C19—C24—C23	−1.6 (3)
C3—C4—C5—C6	172.12 (13)	C18—C19—C24—C23	176.04 (18)
O1—C5—C6—C7	−163.09 (15)	C22—C23—C24—C19	−1.2 (3)
C4—C5—C6—C7	15.9 (2)	N2—C2—C25—C26	26.7 (2)
O1—C5—C6—C11	14.8 (2)	N3—C2—C25—C26	−152.10 (18)
C4—C5—C6—C11	−166.23 (14)	N2—C2—C25—C30	−150.80 (17)
C11—C6—C7—C8	0.6 (2)	N3—C2—C25—C30	30.4 (3)
C5—C6—C7—C8	178.48 (15)	C30—C25—C26—C27	−0.2 (3)
C6—C7—C8—C9	−0.1 (2)	C2—C25—C26—C27	−177.80 (17)
C7—C8—C9—C10	−0.5 (3)	C25—C26—C27—C28	−0.8 (3)
C8—C9—C10—C11	0.8 (3)	C26—C27—C28—C29	0.7 (3)
C9—C10—C11—C6	−0.4 (3)	C27—C28—C29—C30	0.4 (3)
C7—C6—C11—C10	−0.3 (2)	C26—C25—C30—C29	1.4 (3)
C5—C6—C11—C10	−178.26 (15)	C2—C25—C30—C29	178.79 (16)
N1—C3—C12—C13	−47.16 (19)	C28—C29—C30—C25	−1.5 (3)
C4—C3—C12—C13	75.57 (18)