(2R)-2-Cinnamoylamino-N-[5-(4-methoxy-phen-yl)-1,3,4-thia-diazol-2-yl]propanamide.

The asymmetric unit of the title compound, C(21)H(20)N(4)O(3)S, contains two independent mol-ecules. The dihedral angles between the two benzene rings are 47.6 (1) and 30.2 (1)°, the corresponding values between the p-methoxy-benzene and thia-diazol rings are 12.3 (1) and 24.7 (1)°, respectively, for the two mol-ecules. The conformations of the N-H and C=O bonds are anti with respect to each other. The enone groups show a trans configuration. The crystal structure is stabilized by N-H⋯O and N-H⋯N inter-actions. The absolute structure could not be determined from the X-ray data but the absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

Related literature

For 1,3,4-thiadiazole scaffold compounds and their biological activity, see: Tu et al. (2008 ▶). For the synthesis, see: Foroumadi et al. (1999 ▶); Levy & Palmer (1942 ▶); Song et al. (1992 ▶). For related structures, see: Fun et al. (2008 ▶); Gowda et al. (2008 ▶) Thiruvalluvar et al. (2008 ▶).

Experimental

Crystal data

C21H20N4O3S

M = 408.48

Triclinic,

a = 9.082 (3) Å

b = 9.849 (3) Å

c = 13.644 (4) Å

α = 79.587 (4)°

β = 83.253 (4)°

γ = 65.458 (4)°

V = 1090.8 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 296 (2) K

0.35 × 0.24 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

6219 measured reflections

3553 independent reflections

2735 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 0.94

3553 reflections

528 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: APEX2; software used to prepare material for publication: APEX2 and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808027803/im2079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027803/im2079Isup2.hkl

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

C21H20N4O3S	Z = 2
Mr = 408.48	F(000) = 428
Triclinic, P1	Dx = 1.244 Mg m−3
Hall symbol: P 1	Melting point: 450 K
a = 9.082 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.849 (3) Å	Cell parameters from 2616 reflections
c = 13.644 (4) Å	θ = 2.3–25.0°
α = 79.587 (4)°	µ = 0.18 mm−1
β = 83.253 (4)°	T = 296 K
γ = 65.458 (4)°	Bolck, colourles
V = 1090.8 (5) Å3	0.35 × 0.25 × 0.06 mm

Bruker APEXII CCD area-detector diffractometer	2735 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 25.0°, θmin = 2.3°
phi and ω scans	h = −10→10
6219 measured reflections	k = −11→11
3553 independent reflections	l = −16→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0648P)2] where P = (Fo2 + 2Fc2)/3
3553 reflections	(Δ/σ)max < 0.001
528 parameters	Δρmax = 0.20 e Å−3
3 restraints	Δρmin = −0.18 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.# SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.151 0.591 0.943 19.4 0.7 2 0.269 -0.200 0.408 64.4 11.5

	x	y	z	Uiso*/Ueq
C1	−1.0057 (8)	0.2529 (9)	0.5939 (8)	0.166 (4)
H1A	−0.9914	0.3381	0.6089	0.249*
H1B	−1.0630	0.2174	0.6489	0.249*
H1C	−1.0669	0.2824	0.5351	0.249*
C2	−0.7380 (5)	0.1750 (6)	0.5178 (4)	0.0752 (13)
C3	−0.7671 (6)	0.3158 (6)	0.4658 (4)	0.0792 (15)
H3	−0.8694	0.3938	0.4689	0.095*
C4	−0.6419 (5)	0.3393 (5)	0.4090 (4)	0.0699 (12)
H4	−0.6612	0.4347	0.3736	0.084*
C5	−0.4885 (5)	0.2259 (5)	0.4028 (3)	0.0527 (10)
C6	−0.4629 (5)	0.0841 (5)	0.4548 (3)	0.0623 (11)
H6	−0.3611	0.0056	0.4508	0.075*
C7	−0.5874 (6)	0.0576 (6)	0.5131 (4)	0.0764 (13)
H7	−0.5694	−0.0377	0.5483	0.092*
C8	−0.3565 (5)	0.2565 (5)	0.3439 (3)	0.0534 (10)
C9	−0.1214 (5)	0.2590 (5)	0.2508 (3)	0.0532 (10)
C10	0.1343 (5)	0.1053 (4)	0.1705 (3)	0.0510 (10)
C11	0.2964 (5)	0.1100 (5)	0.1366 (3)	0.0565 (10)
H11	0.2780	0.2140	0.1076	0.068*
C12	0.3982 (6)	0.0670 (7)	0.2263 (4)	0.0879 (16)
H12A	0.4259	−0.0374	0.2523	0.132*
H12B	0.3379	0.1281	0.2767	0.132*
H12C	0.4954	0.0831	0.2068	0.132*
C13	0.4459 (4)	0.0663 (4)	−0.0225 (3)	0.0483 (9)
C14	0.5593 (5)	−0.0498 (5)	−0.0819 (3)	0.0544 (10)
H14	0.5798	−0.1511	−0.0612	0.065*
C15	0.6316 (5)	−0.0082 (5)	−0.1650 (3)	0.0589 (10)
H15	0.5954	0.0950	−0.1866	0.071*
C16	0.7605 (5)	−0.1055 (5)	−0.2260 (3)	0.0609 (11)
C17	0.8502 (6)	−0.2567 (6)	−0.1942 (4)	0.0853 (15)
H17	0.8253	−0.3019	−0.1323	0.102*
C18	0.9750 (7)	−0.3400 (7)	−0.2534 (5)	0.106 (2)
H18	1.0335	−0.4416	−0.2305	0.128*
C19	1.0168 (7)	−0.2809 (8)	−0.3434 (5)	0.0972 (18)
H19	1.1035	−0.3401	−0.3816	0.117*
C20	0.9305 (7)	−0.1341 (8)	−0.3774 (4)	0.0917 (17)
H20	0.9566	−0.0923	−0.4401	0.110*
C21	0.8028 (6)	−0.0446 (6)	−0.3194 (3)	0.0773 (14)
H21	0.7454	0.0567	−0.3433	0.093*
C22	1.1903 (8)	−0.0712 (8)	−0.1755 (6)	0.115 (2)
H22A	1.1687	−0.1288	−0.1153	0.173*
H22B	1.2980	−0.1256	−0.2015	0.173*
H22C	1.1135	−0.0544	−0.2238	0.173*
C23	1.0387 (5)	0.1557 (6)	−0.1050 (4)	0.0679 (12)
C24	1.0413 (5)	0.2832 (6)	−0.0771 (4)	0.0708 (13)
H24	1.1329	0.3043	−0.0914	0.085*
C25	0.9095 (5)	0.3767 (5)	−0.0289 (4)	0.0643 (11)
H25	0.9130	0.4609	−0.0092	0.077*
C26	0.7698 (5)	0.3508 (5)	−0.0081 (3)	0.0543 (10)
C27	0.7702 (5)	0.2255 (5)	−0.0358 (4)	0.0681 (12)
H27	0.6773	0.2062	−0.0227	0.082*
C28	0.9036 (6)	0.1251 (6)	−0.0830 (4)	0.0763 (13)
H28	0.9016	0.0383	−0.0994	0.092*
C29	0.6258 (5)	0.4600 (4)	0.0389 (3)	0.0537 (10)
C30	0.3751 (5)	0.6067 (5)	0.1151 (3)	0.0549 (10)
C31	0.1097 (5)	0.6158 (4)	0.1795 (3)	0.0488 (9)
C32	−0.0580 (5)	0.7268 (4)	0.2076 (3)	0.0519 (10)
H32	−0.0476	0.8095	0.2325	0.062*
C33	−0.1544 (6)	0.7907 (6)	0.1143 (4)	0.0846 (15)
H33A	−0.1650	0.7107	0.0887	0.127*
H33B	−0.0993	0.8378	0.0648	0.127*
H33C	−0.2601	0.8641	0.1301	0.127*
C34	−0.1692 (5)	0.6921 (5)	0.3768 (3)	0.0572 (10)
C35	−0.2660 (5)	0.6200 (5)	0.4430 (3)	0.0636 (11)
H35	−0.3026	0.5591	0.4171	0.076*
C36	−0.3019 (5)	0.6389 (5)	0.5363 (3)	0.0638 (11)
H36	−0.2649	0.7022	0.5589	0.077*
C37	−0.3926 (5)	0.5732 (5)	0.6091 (3)	0.0626 (11)
C38	−0.4185 (7)	0.6053 (7)	0.7051 (4)	0.0899 (16)
H38	−0.3807	0.6716	0.7228	0.108*
C39	−0.5020 (8)	0.5383 (9)	0.7766 (4)	0.105 (2)
H39	−0.5189	0.5604	0.8415	0.126*
C40	−0.5591 (7)	0.4401 (7)	0.7516 (5)	0.0953 (18)
H40	−0.6158	0.3970	0.7988	0.114*
C41	−0.5316 (8)	0.4077 (7)	0.6580 (5)	0.0948 (17)
H41	−0.5690	0.3408	0.6408	0.114*
C42	−0.4493 (6)	0.4714 (6)	0.5874 (4)	0.0807 (14)
H42	−0.4310	0.4459	0.5233	0.097*
N1	−0.3581 (4)	0.3920 (4)	0.3237 (3)	0.0643 (9)
N2	−0.2200 (4)	0.3929 (4)	0.2696 (3)	0.0641 (9)
N3	0.0283 (4)	0.2369 (4)	0.2044 (2)	0.0555 (8)
H3A	0.0578	0.3109	0.1960	0.067*
N4	0.3805 (4)	0.0138 (4)	0.0618 (2)	0.0556 (8)
H4A	0.3890	−0.0778	0.0710	0.067*
N5	0.6130 (4)	0.5942 (4)	0.0479 (3)	0.0669 (10)
N6	0.4668 (4)	0.6790 (4)	0.0918 (3)	0.0668 (10)
N7	0.2200 (4)	0.6771 (4)	0.1557 (3)	0.0567 (8)
H7A	0.1911	0.7681	0.1667	0.068*
N8	−0.1393 (4)	0.6583 (4)	0.2839 (3)	0.0603 (9)
H8	−0.1699	0.5930	0.2693	0.072*
O1	0.1002 (3)	−0.0005 (3)	0.1732 (2)	0.0627 (8)
O2	0.4184 (3)	0.2007 (3)	−0.0448 (2)	0.0634 (7)
O4	0.1420 (3)	0.4837 (3)	0.1726 (2)	0.0652 (8)
O5	−0.1232 (5)	0.7795 (4)	0.4039 (2)	0.0849 (10)
O3	−0.8515 (5)	0.1357 (5)	0.5771 (4)	0.1156 (15)
O6	1.1766 (4)	0.0707 (4)	−0.1543 (3)	0.0913 (11)
S1	−0.18753 (12)	0.11853 (11)	0.29467 (8)	0.0607 (3)
S2	0.45630 (12)	0.42627 (11)	0.08513 (8)	0.0581 (3)

	U11	U22	U33	U12	U13	U23
C1	0.080 (4)	0.109 (6)	0.259 (10)	−0.022 (4)	0.080 (6)	0.002 (6)
C2	0.050 (3)	0.069 (3)	0.102 (3)	−0.025 (2)	0.016 (2)	−0.012 (3)
C3	0.051 (3)	0.057 (3)	0.119 (4)	−0.020 (2)	0.010 (3)	−0.001 (3)
C4	0.062 (3)	0.054 (3)	0.090 (3)	−0.023 (2)	0.012 (2)	−0.009 (2)
C5	0.051 (2)	0.052 (2)	0.062 (2)	−0.027 (2)	0.0095 (18)	−0.0178 (19)
C6	0.053 (2)	0.052 (2)	0.076 (3)	−0.018 (2)	0.011 (2)	−0.013 (2)
C7	0.065 (3)	0.064 (3)	0.093 (3)	−0.028 (2)	0.014 (2)	−0.001 (2)
C8	0.056 (2)	0.057 (3)	0.058 (2)	−0.033 (2)	0.0139 (18)	−0.0210 (19)
C9	0.060 (2)	0.052 (2)	0.059 (2)	−0.033 (2)	0.0153 (18)	−0.0218 (18)
C10	0.060 (2)	0.042 (2)	0.057 (2)	−0.029 (2)	0.0127 (19)	−0.0136 (18)
C11	0.063 (2)	0.049 (2)	0.068 (3)	−0.033 (2)	0.019 (2)	−0.023 (2)
C12	0.074 (3)	0.113 (5)	0.086 (4)	−0.040 (3)	0.009 (3)	−0.039 (3)
C13	0.048 (2)	0.047 (2)	0.056 (2)	−0.0267 (19)	0.0089 (17)	−0.0127 (18)
C14	0.049 (2)	0.052 (2)	0.065 (3)	−0.0241 (19)	0.0119 (19)	−0.0139 (19)
C15	0.054 (2)	0.059 (3)	0.067 (3)	−0.027 (2)	0.0130 (19)	−0.015 (2)
C16	0.058 (2)	0.067 (3)	0.060 (2)	−0.027 (2)	0.0108 (19)	−0.020 (2)
C17	0.082 (3)	0.079 (4)	0.075 (3)	−0.020 (3)	0.022 (3)	−0.011 (3)
C18	0.091 (4)	0.089 (4)	0.104 (4)	−0.010 (3)	0.036 (3)	−0.020 (3)
C19	0.084 (4)	0.097 (5)	0.096 (4)	−0.022 (3)	0.030 (3)	−0.036 (3)
C20	0.094 (4)	0.114 (5)	0.067 (3)	−0.045 (4)	0.033 (3)	−0.029 (3)
C21	0.071 (3)	0.082 (3)	0.070 (3)	−0.028 (3)	0.023 (2)	−0.012 (2)
C22	0.077 (4)	0.108 (5)	0.150 (6)	−0.013 (3)	0.020 (4)	−0.066 (4)
C23	0.053 (2)	0.066 (3)	0.077 (3)	−0.015 (2)	0.006 (2)	−0.018 (2)
C24	0.050 (3)	0.067 (3)	0.096 (3)	−0.029 (2)	0.013 (2)	−0.010 (3)
C25	0.053 (2)	0.050 (2)	0.095 (3)	−0.025 (2)	0.007 (2)	−0.018 (2)
C26	0.046 (2)	0.048 (2)	0.070 (3)	−0.0207 (19)	0.0022 (19)	−0.011 (2)
C27	0.051 (2)	0.060 (3)	0.096 (3)	−0.024 (2)	0.009 (2)	−0.021 (2)
C28	0.058 (3)	0.072 (3)	0.105 (4)	−0.024 (2)	0.012 (2)	−0.042 (3)
C29	0.047 (2)	0.047 (2)	0.069 (2)	−0.0249 (19)	0.0118 (18)	−0.0095 (19)
C30	0.057 (2)	0.043 (2)	0.069 (2)	−0.026 (2)	0.0072 (19)	−0.0100 (18)
C31	0.058 (2)	0.039 (2)	0.057 (2)	−0.0277 (19)	0.0127 (18)	−0.0125 (17)
C32	0.050 (2)	0.038 (2)	0.074 (3)	−0.0247 (18)	0.0155 (19)	−0.0167 (18)
C33	0.066 (3)	0.076 (3)	0.099 (4)	−0.024 (3)	0.005 (3)	0.001 (3)
C34	0.059 (2)	0.048 (2)	0.069 (3)	−0.028 (2)	0.014 (2)	−0.016 (2)
C35	0.064 (2)	0.057 (3)	0.079 (3)	−0.034 (2)	0.023 (2)	−0.023 (2)
C36	0.069 (3)	0.060 (3)	0.068 (3)	−0.033 (2)	0.011 (2)	−0.015 (2)
C37	0.067 (3)	0.061 (3)	0.055 (3)	−0.023 (2)	0.007 (2)	−0.006 (2)
C38	0.092 (4)	0.106 (4)	0.069 (3)	−0.041 (3)	0.008 (3)	−0.012 (3)
C39	0.108 (5)	0.130 (6)	0.054 (3)	−0.035 (4)	0.015 (3)	−0.002 (3)
C40	0.089 (4)	0.076 (4)	0.094 (4)	−0.023 (3)	0.020 (3)	0.013 (3)
C41	0.106 (4)	0.088 (4)	0.091 (4)	−0.053 (3)	0.027 (3)	0.001 (3)
C42	0.085 (3)	0.087 (4)	0.072 (3)	−0.042 (3)	0.025 (3)	−0.019 (3)
N1	0.063 (2)	0.056 (2)	0.082 (2)	−0.0328 (18)	0.0229 (18)	−0.0271 (18)
N2	0.063 (2)	0.049 (2)	0.089 (2)	−0.0322 (18)	0.0261 (18)	−0.0242 (17)
N3	0.062 (2)	0.0433 (18)	0.072 (2)	−0.0322 (16)	0.0236 (16)	−0.0238 (15)
N4	0.0623 (19)	0.0468 (19)	0.065 (2)	−0.0313 (17)	0.0236 (16)	−0.0196 (15)
N5	0.056 (2)	0.048 (2)	0.101 (3)	−0.0282 (18)	0.0176 (19)	−0.0173 (19)
N6	0.058 (2)	0.0465 (19)	0.104 (3)	−0.0307 (18)	0.0243 (19)	−0.0248 (18)
N7	0.0534 (19)	0.0418 (18)	0.082 (2)	−0.0264 (16)	0.0183 (16)	−0.0238 (16)
N8	0.065 (2)	0.055 (2)	0.076 (2)	−0.0396 (18)	0.0288 (17)	−0.0303 (17)
O1	0.0621 (17)	0.0437 (17)	0.091 (2)	−0.0305 (15)	0.0205 (15)	−0.0235 (14)
O2	0.0660 (17)	0.0498 (17)	0.0777 (18)	−0.0317 (14)	0.0192 (14)	−0.0115 (14)
O4	0.0617 (17)	0.0434 (17)	0.096 (2)	−0.0289 (14)	0.0228 (15)	−0.0224 (15)
O5	0.117 (3)	0.094 (2)	0.078 (2)	−0.076 (2)	0.0206 (19)	−0.0272 (18)
O3	0.075 (2)	0.089 (3)	0.164 (4)	−0.037 (2)	0.050 (2)	0.000 (3)
O6	0.0564 (18)	0.097 (3)	0.120 (3)	−0.0218 (18)	0.0247 (18)	−0.054 (2)
S1	0.0587 (6)	0.0450 (6)	0.0840 (7)	−0.0289 (5)	0.0226 (5)	−0.0203 (5)
S2	0.0546 (6)	0.0436 (5)	0.0817 (7)	−0.0264 (5)	0.0176 (5)	−0.0201 (5)

C1—O3	1.423 (7)	C22—H22C	0.9600
C1—H1A	0.9600	C23—O6	1.362 (5)
C1—H1B	0.9600	C23—C28	1.369 (7)
C1—H1C	0.9600	C23—C24	1.387 (7)
C2—C3	1.371 (7)	C24—C25	1.353 (6)
C2—O3	1.375 (5)	C24—H24	0.9300
C2—C7	1.380 (7)	C25—C26	1.384 (6)
C3—C4	1.376 (6)	C25—H25	0.9300
C3—H3	0.9300	C26—C27	1.353 (6)
C4—C5	1.382 (6)	C26—C29	1.471 (6)
C4—H4	0.9300	C27—C28	1.382 (6)
C5—C6	1.385 (6)	C27—H27	0.9300
C5—C8	1.470 (5)	C28—H28	0.9300
C6—C7	1.392 (6)	C29—N5	1.305 (5)
C6—H6	0.9300	C29—S2	1.732 (4)
C7—H7	0.9300	C30—N6	1.284 (5)
C8—N1	1.307 (5)	C30—N7	1.384 (5)
C8—S1	1.734 (4)	C30—S2	1.724 (4)
C9—N2	1.302 (5)	C31—O4	1.228 (4)
C9—N3	1.378 (5)	C31—N7	1.353 (5)
C9—S1	1.715 (4)	C31—C32	1.514 (5)
C10—O1	1.198 (4)	C32—N8	1.437 (5)
C10—N3	1.378 (5)	C32—C33	1.516 (7)
C10—C11	1.507 (5)	C32—H32	0.9800
C11—N4	1.445 (5)	C33—H33A	0.9600
C11—C12	1.511 (7)	C33—H33B	0.9600
C11—H11	0.9800	C33—H33C	0.9600
C12—H12A	0.9600	C34—O5	1.225 (5)
C12—H12B	0.9600	C34—N8	1.337 (5)
C12—H12C	0.9600	C34—C35	1.481 (6)
C13—O2	1.227 (4)	C35—C36	1.303 (6)
C13—N4	1.349 (5)	C35—H35	0.9300
C13—C14	1.478 (5)	C36—C37	1.450 (6)
C14—C15	1.330 (5)	C36—H36	0.9300
C14—H14	0.9300	C37—C38	1.374 (7)
C15—C16	1.452 (6)	C37—C42	1.389 (7)
C15—H15	0.9300	C38—C39	1.404 (8)
C16—C17	1.383 (7)	C38—H38	0.9300
C16—C21	1.390 (6)	C39—C40	1.377 (9)
C17—C18	1.364 (7)	C39—H39	0.9300
C17—H17	0.9300	C40—C41	1.342 (9)
C18—C19	1.345 (8)	C40—H40	0.9300
C18—H18	0.9300	C41—C42	1.373 (7)
C19—C20	1.350 (8)	C41—H41	0.9300
C19—H19	0.9300	C42—H42	0.9300
C20—C21	1.391 (7)	N1—N2	1.381 (5)
C20—H20	0.9300	N3—H3A	0.8600
C21—H21	0.9300	N4—H4A	0.8600
C22—O6	1.430 (8)	N5—N6	1.376 (5)
C22—H22A	0.9600	N7—H7A	0.8600
C22—H22B	0.9600	N8—H8	0.8600
C3—C2—O3	124.8 (4)	C27—C26—C29	122.2 (4)
C3—C2—C7	121.4 (4)	C25—C26—C29	120.2 (4)
O3—C2—C7	113.8 (4)	C26—C27—C28	122.4 (4)
C2—C3—C4	118.7 (4)	C26—C27—H27	118.8
C2—C3—H3	120.7	C28—C27—H27	118.8
C4—C3—H3	120.7	C23—C28—C27	118.9 (5)
C3—C4—C5	122.2 (4)	C23—C28—H28	120.6
C3—C4—H4	118.9	C27—C28—H28	120.6
C5—C4—H4	118.9	N5—C29—C26	122.5 (3)
C4—C5—C6	118.0 (4)	N5—C29—S2	113.4 (3)
C4—C5—C8	120.6 (4)	C26—C29—S2	124.0 (3)
C6—C5—C8	121.4 (4)	N6—C30—N7	120.2 (4)
C5—C6—C7	120.9 (4)	N6—C30—S2	115.0 (3)
C5—C6—H6	119.5	N7—C30—S2	124.7 (3)
C7—C6—H6	119.5	O4—C31—N7	122.2 (4)
C2—C7—C6	118.8 (4)	O4—C31—C32	123.6 (3)
C2—C7—H7	120.6	N7—C31—C32	114.1 (3)
C6—C7—H7	120.6	N8—C32—C31	112.0 (3)
N1—C8—C5	122.2 (4)	N8—C32—C33	110.8 (3)
N1—C8—S1	114.3 (3)	C31—C32—C33	108.2 (4)
C5—C8—S1	123.5 (3)	N8—C32—H32	108.6
N2—C9—N3	119.9 (3)	C31—C32—H32	108.6
N2—C9—S1	115.2 (3)	C33—C32—H32	108.6
N3—C9—S1	124.8 (3)	O5—C34—N8	122.2 (4)
O1—C10—N3	122.5 (3)	O5—C34—C35	122.8 (4)
O1—C10—C11	125.7 (4)	N8—C34—C35	115.0 (4)
N3—C10—C11	111.7 (3)	C36—C35—C34	122.4 (4)
N4—C11—C10	112.7 (3)	C36—C35—H35	118.8
N4—C11—C12	110.7 (4)	C34—C35—H35	118.8
C10—C11—C12	109.0 (3)	C35—C36—C37	127.8 (5)
N4—C11—H11	108.1	C35—C36—H36	116.1
C10—C11—H11	108.1	C37—C36—H36	116.1
C12—C11—H11	108.1	C38—C37—C42	117.4 (4)
O2—C13—N4	121.6 (3)	C38—C37—C36	120.0 (5)
O2—C13—C14	122.8 (3)	C42—C37—C36	122.5 (4)
N4—C13—C14	115.4 (3)	C37—C38—C39	120.1 (6)
C15—C14—C13	119.4 (4)	C37—C38—H38	119.9
C15—C14—H14	120.3	C39—C38—H38	119.9
C13—C14—H14	120.3	C40—C39—C38	120.7 (6)
C14—C15—C16	127.4 (4)	C40—C39—H39	119.7
C14—C15—H15	116.3	C38—C39—H39	119.7
C16—C15—H15	116.3	C41—C40—C39	119.0 (5)
C17—C16—C21	117.2 (4)	C41—C40—H40	120.5
C17—C16—C15	123.3 (4)	C39—C40—H40	120.5
C21—C16—C15	119.4 (4)	C40—C41—C42	121.1 (6)
C18—C17—C16	120.2 (5)	C40—C41—H41	119.4
C18—C17—H17	119.9	C42—C41—H41	119.4
C16—C17—H17	119.9	C41—C42—C37	121.7 (5)
C19—C18—C17	122.5 (6)	C41—C42—H42	119.2
C19—C18—H18	118.7	C37—C42—H42	119.2
C17—C18—H18	118.7	C8—N1—N2	112.0 (3)
C18—C19—C20	118.8 (5)	C9—N2—N1	112.1 (3)
C18—C19—H19	120.6	C9—N3—C10	124.9 (3)
C20—C19—H19	120.6	C9—N3—H3A	117.6
C19—C20—C21	120.6 (5)	C10—N3—H3A	117.6
C19—C20—H20	119.7	C13—N4—C11	120.7 (3)
C21—C20—H20	119.7	C13—N4—H4A	119.7
C16—C21—C20	120.5 (5)	C11—N4—H4A	119.7
C16—C21—H21	119.7	C29—N5—N6	112.9 (3)
C20—C21—H21	119.7	C30—N6—N5	112.2 (3)
O6—C23—C28	125.5 (5)	C31—N7—C30	126.0 (3)
O6—C23—C24	114.7 (4)	C31—N7—H7A	117.0
C28—C23—C24	119.7 (4)	C30—N7—H7A	117.0
C25—C24—C23	119.5 (4)	C34—N8—C32	122.6 (3)
C25—C24—H24	120.2	C34—N8—H8	118.7
C23—C24—H24	120.2	C32—N8—H8	118.7
C24—C25—C26	121.9 (4)	C2—O3—C1	117.5 (5)
C24—C25—H25	119.0	C23—O6—C22	117.9 (4)
C26—C25—H25	119.0	C9—S1—C8	86.3 (2)
C27—C26—C25	117.5 (4)	C30—S2—C29	86.49 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.86	2.10	2.960 (4)	177.
N4—H4A···N6i	0.86	2.17	3.016 (5)	168.
N7—H7A···O1ii	0.86	2.09	2.944 (4)	171.
N8—H8···N2	0.86	2.20	3.036 (5)	165.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O4	0.86	2.10	2.960 (4)	177
N4—H4A⋯N6i	0.86	2.17	3.016 (5)	168
N7—H7A⋯O1ii	0.86	2.09	2.944 (4)	171
N8—H8⋯N2	0.86	2.20	3.036 (5)	165

Symmetry codes: (i) ; (ii) .