1-{2-[(Anthracen-10-yl)methyl-ene-amino]phen-yl}-3-phenyl-thio-urea.

The title compound, C(28)H(21)N(3)S, crystallizes with two mol-ecules in the asymmetric unit. There are only very slight differences in the torsion angles between the two molecules. The two mol-ecules are stabilized by intra-molecular N-H⋯N inter-actions and the crystal packing is stabilized by inter-molecular N-H⋯S inter-actions.

Related literature

For related literature, see: Lee et al. (2003 ▶, 2005 ▶); Gayathri et al. (2007 ▶); Yoon et al. (2004 ▶).

Experimental

Crystal data

C28H21N3S

M = 431.54

Triclinic,

a = 6.6148 (6) Å

b = 14.3154 (12) Å

c = 23.823 (2) Å

α = 74.045 (1)°

β = 88.705 (1)°

γ = 87.421 (1)°

V = 2166.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 293 (2) K

0.27 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

25075 measured reflections

9927 independent reflections

7972 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 1.01

9927 reflections

577 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068729/at2524sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068729/at2524Isup2.hkl

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

C28H21N3S	Z = 4
Mr = 431.54	F000 = 904
Triclinic, P1	Dx = 1.323 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.6148 (6) Å	Cell parameters from 4967 reflections
b = 14.3154 (12) Å	θ = 0.9–25.0º
c = 23.823 (2) Å	µ = 0.17 mm−1
α = 74.045 (1)º	T = 293 (2) K
β = 88.705 (1)º	Block, orange
γ = 87.421 (1)º	0.27 × 0.25 × 0.20 mm
V = 2166.7 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	7972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Monochromator: graphite	θmax = 28.0º
T = 293(2) K	θmin = 0.9º
ω scans	h = −8→8
Absorption correction: none	k = −18→18
25075 measured reflections	l = −31→30
9927 independent 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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0719P)2 + 0.4912P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
9927 reflections	Δρmax = 0.30 e Å−3
577 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	1.0750 (3)	0.83551 (13)	0.43543 (8)	0.0668 (5)
H1	0.9428	0.8512	0.4226	0.080*
C2	1.2051 (4)	0.90827 (15)	0.43618 (9)	0.0824 (7)
H2	1.1604	0.9730	0.4227	0.099*
C3	1.4005 (4)	0.88623 (17)	0.45663 (9)	0.0757 (6)
H3	1.4874	0.9357	0.4563	0.091*
C4	1.4646 (3)	0.79053 (17)	0.47747 (9)	0.0661 (5)
H4	1.5937	0.7750	0.4928	0.079*
C5	1.3389 (3)	0.71766 (14)	0.47575 (8)	0.0549 (4)
H5	1.3847	0.6531	0.4893	0.066*
C6	1.1435 (2)	0.73914 (12)	0.45391 (6)	0.0453 (3)
C7	0.8606 (2)	0.64513 (10)	0.42670 (7)	0.0407 (3)
C8	0.6251 (2)	0.73651 (10)	0.34664 (6)	0.0388 (3)
C9	0.4771 (3)	0.67024 (12)	0.34774 (7)	0.0499 (4)
H9	0.4953	0.6061	0.3700	0.060*
C10	0.3022 (3)	0.69976 (13)	0.31565 (8)	0.0533 (4)
H10	0.2026	0.6553	0.3172	0.064*
C11	0.2736 (3)	0.79363 (13)	0.28152 (8)	0.0548 (4)
H11	0.1544	0.8129	0.2608	0.066*
C12	0.4229 (3)	0.85882 (12)	0.27830 (8)	0.0529 (4)
H12	0.4054	0.9219	0.2544	0.063*
C13	0.5993 (2)	0.83184 (10)	0.31016 (7)	0.0405 (3)
C14	0.7895 (2)	0.96526 (11)	0.26658 (7)	0.0455 (4)
H14	0.7202	0.9697	0.2323	0.055*
C15	0.9408 (2)	1.03762 (10)	0.26697 (7)	0.0414 (3)
C16	1.0866 (2)	1.05835 (10)	0.22175 (7)	0.0428 (3)
C17	1.0824 (3)	1.02141 (12)	0.17182 (8)	0.0554 (4)
H17	0.9750	0.9845	0.1673	0.067*
C18	1.2331 (4)	1.03941 (15)	0.13084 (9)	0.0704 (6)
H18	1.2263	1.0153	0.0985	0.084*
C19	1.3993 (4)	1.09424 (16)	0.13679 (10)	0.0738 (6)
H19	1.5029	1.1044	0.1090	0.089*
C20	1.4083 (3)	1.13178 (13)	0.18254 (9)	0.0627 (5)
H20	1.5178	1.1685	0.1857	0.075*
C21	1.2538 (2)	1.11652 (11)	0.22630 (7)	0.0473 (4)
C22	1.2633 (3)	1.15498 (11)	0.27368 (8)	0.0527 (4)
H22	1.3740	1.1908	0.2770	0.063*
C23	1.1118 (3)	1.14130 (11)	0.31620 (7)	0.0512 (4)
C24	1.1149 (4)	1.18661 (14)	0.36275 (9)	0.0726 (6)
H24	1.2239	1.2235	0.3661	0.087*
C25	0.9601 (5)	1.17627 (17)	0.40198 (10)	0.0892 (8)
H25	0.9639	1.2060	0.4321	0.107*
C26	0.7947 (5)	1.12125 (17)	0.39754 (10)	0.0862 (7)
H26	0.6877	1.1167	0.4240	0.103*
C27	0.7874 (3)	1.07436 (14)	0.35527 (9)	0.0640 (5)
H27	0.6774	1.0369	0.3539	0.077*
C28	0.9462 (3)	1.08186 (11)	0.31304 (7)	0.0464 (4)
C29	0.8250 (2)	0.82162 (12)	0.11334 (8)	0.0498 (4)
H29	0.8800	0.8707	0.0836	0.060*
C30	0.9403 (3)	0.77475 (14)	0.16104 (9)	0.0596 (5)
H30	1.0722	0.7931	0.1636	0.071*
C31	0.8624 (3)	0.70121 (14)	0.20488 (9)	0.0660 (5)
H31	0.9413	0.6693	0.2368	0.079*
C32	0.6657 (3)	0.67491 (14)	0.20117 (8)	0.0663 (5)
H32	0.6130	0.6246	0.2306	0.080*
C33	0.5464 (3)	0.72254 (13)	0.15422 (7)	0.0564 (4)
H33	0.4130	0.7056	0.1526	0.068*
C34	0.6266 (2)	0.79581 (11)	0.10948 (7)	0.0423 (3)
C35	0.3493 (2)	0.83579 (10)	0.03364 (6)	0.0393 (3)
C36	0.1103 (2)	0.70265 (10)	0.03509 (6)	0.0372 (3)
C37	−0.0307 (2)	0.74808 (12)	−0.00702 (7)	0.0469 (4)
H37	−0.0083	0.8100	−0.0311	0.056*
C38	−0.2040 (3)	0.70172 (13)	−0.01336 (8)	0.0531 (4)
H38	−0.2979	0.7331	−0.0415	0.064*
C39	−0.2395 (3)	0.61000 (14)	0.02130 (8)	0.0615 (5)
H39	−0.3570	0.5794	0.0170	0.074*
C40	−0.0983 (3)	0.56365 (13)	0.06269 (8)	0.0586 (5)
H40	−0.1209	0.5011	0.0859	0.070*
C41	0.0756 (2)	0.60844 (11)	0.07029 (6)	0.0411 (3)
C42	0.1800 (2)	0.50230 (11)	0.15842 (7)	0.0450 (3)
H42	0.0437	0.4950	0.1683	0.054*
C43	0.3335 (2)	0.44540 (10)	0.19903 (7)	0.0427 (3)
C44	0.3104 (3)	0.43694 (11)	0.25943 (7)	0.0473 (4)
C45	0.1310 (3)	0.46802 (12)	0.28476 (8)	0.0593 (5)
H45	0.0216	0.4948	0.2610	0.071*
C46	0.1176 (4)	0.45915 (14)	0.34297 (9)	0.0736 (6)
H46	−0.0025	0.4777	0.3587	0.088*
C47	0.2841 (5)	0.42199 (16)	0.37991 (9)	0.0795 (7)
H47	0.2748	0.4190	0.4194	0.095*
C48	0.4553 (4)	0.39112 (15)	0.35819 (8)	0.0699 (6)
H48	0.5633	0.3669	0.3831	0.084*
C49	0.4761 (3)	0.39443 (12)	0.29795 (7)	0.0545 (4)
C50	0.6473 (3)	0.35753 (13)	0.27574 (8)	0.0573 (5)
H50	0.7555	0.3331	0.3005	0.069*
C51	0.6633 (2)	0.35574 (11)	0.21783 (7)	0.0500 (4)
C52	0.8315 (3)	0.30881 (13)	0.19662 (9)	0.0620 (5)
H52	0.9389	0.2830	0.2214	0.074*
C53	0.8381 (3)	0.30117 (14)	0.14154 (10)	0.0660 (5)
H53	0.9487	0.2699	0.1287	0.079*
C54	0.6768 (3)	0.34067 (13)	0.10326 (9)	0.0587 (4)
H54	0.6796	0.3329	0.0658	0.070*
C55	0.5179 (3)	0.38982 (11)	0.12048 (7)	0.0486 (4)
H55	0.4162	0.4173	0.0940	0.058*
C56	0.5029 (2)	0.40045 (10)	0.17814 (7)	0.0426 (3)
N1	1.0247 (2)	0.65807 (9)	0.45631 (6)	0.0500 (3)
H1A	1.0655	0.6061	0.4820	0.060*
N2	0.8043 (2)	0.71818 (9)	0.38004 (6)	0.0456 (3)
H2A	0.8932	0.7616	0.3684	0.055*
N3	0.75168 (19)	0.89754 (9)	0.31147 (6)	0.0452 (3)
N4	0.5165 (2)	0.85242 (9)	0.06068 (6)	0.0485 (3)
H4A	0.5654	0.9084	0.0452	0.058*
N5	0.29052 (19)	0.74304 (9)	0.04688 (6)	0.0436 (3)
H5A	0.3786	0.7009	0.0659	0.052*
N6	0.22933 (19)	0.56134 (9)	0.11000 (6)	0.0435 (3)
S1	0.74429 (7)	0.53913 (3)	0.45046 (2)	0.05533 (13)
S2	0.23302 (6)	0.93114 (3)	−0.01346 (2)	0.05342 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0887 (14)	0.0436 (9)	0.0634 (11)	−0.0040 (9)	−0.0342 (10)	−0.0039 (8)
C2	0.132 (2)	0.0445 (10)	0.0649 (12)	−0.0186 (12)	−0.0358 (13)	−0.0002 (9)
C3	0.1011 (17)	0.0719 (14)	0.0559 (11)	−0.0431 (13)	−0.0029 (11)	−0.0140 (10)
C4	0.0545 (11)	0.0793 (14)	0.0698 (12)	−0.0173 (10)	0.0013 (9)	−0.0274 (11)
C5	0.0492 (9)	0.0562 (10)	0.0595 (10)	−0.0036 (8)	−0.0024 (8)	−0.0156 (8)
C6	0.0528 (9)	0.0423 (8)	0.0377 (8)	−0.0060 (7)	−0.0069 (6)	−0.0045 (6)
C7	0.0406 (7)	0.0336 (7)	0.0435 (8)	0.0008 (6)	−0.0049 (6)	−0.0032 (6)
C8	0.0415 (7)	0.0345 (7)	0.0373 (7)	−0.0041 (6)	−0.0073 (6)	−0.0038 (6)
C9	0.0583 (10)	0.0373 (8)	0.0486 (9)	−0.0115 (7)	−0.0134 (7)	−0.0002 (7)
C10	0.0507 (9)	0.0484 (9)	0.0589 (10)	−0.0162 (7)	−0.0136 (7)	−0.0083 (8)
C11	0.0455 (9)	0.0490 (9)	0.0672 (11)	−0.0035 (7)	−0.0212 (8)	−0.0092 (8)
C12	0.0500 (9)	0.0354 (8)	0.0672 (11)	−0.0011 (7)	−0.0186 (8)	−0.0025 (7)
C13	0.0406 (7)	0.0329 (7)	0.0457 (8)	−0.0040 (6)	−0.0078 (6)	−0.0055 (6)
C14	0.0452 (8)	0.0364 (7)	0.0498 (9)	−0.0024 (6)	−0.0141 (7)	−0.0021 (6)
C15	0.0448 (8)	0.0279 (6)	0.0455 (8)	−0.0017 (6)	−0.0099 (6)	0.0007 (6)
C16	0.0477 (8)	0.0284 (7)	0.0458 (8)	0.0022 (6)	−0.0096 (6)	0.0009 (6)
C17	0.0681 (11)	0.0430 (9)	0.0516 (10)	0.0030 (8)	−0.0110 (8)	−0.0069 (7)
C18	0.0955 (16)	0.0606 (12)	0.0484 (10)	0.0151 (11)	0.0003 (10)	−0.0065 (9)
C19	0.0757 (14)	0.0616 (12)	0.0665 (13)	0.0092 (11)	0.0179 (11)	0.0087 (10)
C20	0.0554 (10)	0.0448 (9)	0.0731 (13)	−0.0020 (8)	0.0060 (9)	0.0082 (9)
C21	0.0471 (8)	0.0304 (7)	0.0549 (9)	−0.0010 (6)	−0.0060 (7)	0.0046 (6)
C22	0.0544 (9)	0.0330 (7)	0.0645 (10)	−0.0110 (7)	−0.0154 (8)	−0.0003 (7)
C23	0.0677 (11)	0.0318 (7)	0.0502 (9)	−0.0048 (7)	−0.0142 (8)	−0.0034 (7)
C24	0.1128 (18)	0.0435 (10)	0.0621 (12)	−0.0131 (11)	−0.0221 (12)	−0.0124 (9)
C25	0.156 (3)	0.0593 (13)	0.0565 (12)	−0.0048 (15)	−0.0014 (15)	−0.0237 (10)
C26	0.129 (2)	0.0610 (13)	0.0683 (14)	−0.0083 (14)	0.0262 (14)	−0.0183 (11)
C27	0.0812 (13)	0.0460 (10)	0.0611 (11)	−0.0065 (9)	0.0113 (10)	−0.0086 (8)
C28	0.0571 (9)	0.0305 (7)	0.0460 (8)	−0.0021 (6)	−0.0057 (7)	−0.0007 (6)
C29	0.0455 (9)	0.0467 (9)	0.0562 (10)	−0.0021 (7)	−0.0099 (7)	−0.0116 (7)
C30	0.0490 (9)	0.0618 (11)	0.0711 (12)	0.0055 (8)	−0.0229 (8)	−0.0231 (10)
C31	0.0815 (13)	0.0551 (11)	0.0612 (11)	0.0114 (10)	−0.0356 (10)	−0.0150 (9)
C32	0.0912 (15)	0.0551 (11)	0.0465 (10)	−0.0107 (10)	−0.0176 (9)	−0.0009 (8)
C33	0.0576 (10)	0.0574 (10)	0.0483 (9)	−0.0124 (8)	−0.0103 (8)	−0.0025 (8)
C34	0.0426 (8)	0.0373 (7)	0.0453 (8)	0.0005 (6)	−0.0106 (6)	−0.0079 (6)
C35	0.0352 (7)	0.0360 (7)	0.0416 (7)	−0.0021 (6)	−0.0029 (6)	−0.0020 (6)
C36	0.0371 (7)	0.0351 (7)	0.0370 (7)	−0.0019 (6)	−0.0050 (5)	−0.0054 (6)
C37	0.0505 (9)	0.0402 (8)	0.0446 (8)	−0.0025 (7)	−0.0131 (7)	−0.0014 (6)
C38	0.0500 (9)	0.0536 (10)	0.0511 (9)	−0.0028 (7)	−0.0204 (7)	−0.0050 (8)
C39	0.0524 (10)	0.0588 (11)	0.0668 (11)	−0.0167 (8)	−0.0214 (8)	−0.0028 (9)
C40	0.0595 (10)	0.0439 (9)	0.0632 (11)	−0.0145 (8)	−0.0194 (8)	0.0044 (8)
C41	0.0422 (8)	0.0354 (7)	0.0423 (8)	−0.0016 (6)	−0.0088 (6)	−0.0042 (6)
C42	0.0443 (8)	0.0364 (7)	0.0496 (9)	−0.0059 (6)	−0.0089 (7)	−0.0027 (6)
C43	0.0488 (8)	0.0301 (7)	0.0445 (8)	−0.0099 (6)	−0.0111 (6)	−0.0003 (6)
C44	0.0624 (10)	0.0293 (7)	0.0474 (8)	−0.0131 (7)	−0.0077 (7)	−0.0033 (6)
C45	0.0802 (13)	0.0384 (8)	0.0576 (10)	−0.0085 (8)	−0.0003 (9)	−0.0093 (8)
C46	0.1098 (18)	0.0483 (10)	0.0660 (13)	−0.0177 (11)	0.0168 (12)	−0.0202 (9)
C47	0.139 (2)	0.0554 (12)	0.0477 (11)	−0.0326 (13)	−0.0053 (13)	−0.0151 (9)
C48	0.1050 (17)	0.0554 (11)	0.0480 (10)	−0.0246 (11)	−0.0185 (11)	−0.0072 (9)
C49	0.0767 (12)	0.0377 (8)	0.0451 (9)	−0.0212 (8)	−0.0178 (8)	−0.0003 (7)
C50	0.0595 (10)	0.0477 (9)	0.0557 (10)	−0.0130 (8)	−0.0242 (8)	0.0044 (8)
C51	0.0485 (9)	0.0358 (8)	0.0562 (10)	−0.0107 (7)	−0.0150 (7)	0.0060 (7)
C52	0.0464 (9)	0.0461 (9)	0.0779 (13)	−0.0008 (7)	−0.0127 (8)	0.0099 (9)
C53	0.0557 (11)	0.0487 (10)	0.0820 (14)	0.0014 (8)	0.0086 (10)	−0.0001 (9)
C54	0.0654 (11)	0.0454 (9)	0.0600 (11)	−0.0072 (8)	0.0055 (9)	−0.0053 (8)
C55	0.0531 (9)	0.0383 (8)	0.0486 (9)	−0.0064 (7)	−0.0064 (7)	−0.0011 (7)
C56	0.0452 (8)	0.0287 (7)	0.0472 (8)	−0.0089 (6)	−0.0111 (6)	0.0027 (6)
N1	0.0529 (8)	0.0357 (6)	0.0524 (8)	−0.0039 (6)	−0.0181 (6)	0.0048 (6)
N2	0.0462 (7)	0.0360 (6)	0.0461 (7)	−0.0118 (5)	−0.0124 (5)	0.0054 (5)
N3	0.0439 (7)	0.0313 (6)	0.0547 (8)	−0.0045 (5)	−0.0142 (6)	−0.0009 (5)
N4	0.0442 (7)	0.0377 (7)	0.0549 (8)	−0.0094 (5)	−0.0144 (6)	0.0042 (6)
N5	0.0390 (6)	0.0337 (6)	0.0508 (7)	−0.0011 (5)	−0.0137 (5)	0.0015 (5)
N6	0.0452 (7)	0.0324 (6)	0.0471 (7)	−0.0041 (5)	−0.0120 (5)	0.0001 (5)
S1	0.0498 (2)	0.0344 (2)	0.0690 (3)	−0.00536 (16)	−0.01566 (19)	0.00915 (18)
S2	0.0460 (2)	0.0368 (2)	0.0651 (3)	−0.00503 (16)	−0.01748 (18)	0.00861 (18)

C1—C2	1.385 (3)	C29—H29	0.9300
C1—C6	1.386 (2)	C30—C31	1.373 (3)
C1—H1	0.9300	C30—H30	0.9300
C2—C3	1.384 (3)	C31—C32	1.382 (3)
C2—H2	0.9300	C31—H31	0.9300
C3—C4	1.373 (3)	C32—C33	1.382 (2)
C3—H3	0.9300	C32—H32	0.9300
C4—C5	1.373 (3)	C33—C34	1.388 (2)
C4—H4	0.9300	C33—H33	0.9300
C5—C6	1.393 (2)	C34—N4	1.4164 (18)
C5—H5	0.9300	C35—N5	1.3506 (19)
C6—N1	1.418 (2)	C35—N4	1.3545 (19)
C7—N2	1.3462 (18)	C35—S2	1.6782 (14)
C7—N1	1.354 (2)	C36—C37	1.3884 (19)
C7—S1	1.6818 (15)	C36—C41	1.404 (2)
C8—C9	1.389 (2)	C36—N5	1.4146 (18)
C8—C13	1.4073 (19)	C37—C38	1.382 (2)
C8—N2	1.4164 (18)	C37—H37	0.9300
C9—C10	1.385 (2)	C38—C39	1.373 (2)
C9—H9	0.9300	C38—H38	0.9300
C10—C11	1.373 (2)	C39—C40	1.382 (2)
C10—H10	0.9300	C39—H39	0.9300
C11—C12	1.376 (2)	C40—C41	1.381 (2)
C11—H11	0.9300	C40—H40	0.9300
C12—C13	1.387 (2)	C41—N6	1.4192 (18)
C12—H12	0.9300	C42—N6	1.274 (2)
C13—N3	1.4159 (18)	C42—C43	1.472 (2)
C14—N3	1.259 (2)	C42—H42	0.9300
C14—C15	1.475 (2)	C43—C56	1.415 (2)
C14—H14	0.9300	C43—C44	1.416 (2)
C15—C16	1.408 (2)	C44—C45	1.427 (3)
C15—C28	1.412 (2)	C44—C49	1.446 (2)
C16—C17	1.430 (2)	C45—C46	1.359 (3)
C16—C21	1.437 (2)	C45—H45	0.9300
C17—C18	1.361 (3)	C46—C47	1.416 (3)
C17—H17	0.9300	C46—H46	0.9300
C18—C19	1.411 (3)	C47—C48	1.341 (3)
C18—H18	0.9300	C47—H47	0.9300
C19—C20	1.345 (3)	C48—C49	1.427 (3)
C19—H19	0.9300	C48—H48	0.9300
C20—C21	1.423 (3)	C49—C50	1.384 (3)
C20—H20	0.9300	C50—C51	1.388 (3)
C21—C22	1.389 (3)	C50—H50	0.9300
C22—C23	1.390 (3)	C51—C52	1.428 (3)
C22—H22	0.9300	C51—C56	1.443 (2)
C23—C24	1.431 (3)	C52—C53	1.346 (3)
C23—C28	1.432 (2)	C52—H52	0.9300
C24—C25	1.356 (4)	C53—C54	1.412 (3)
C24—H24	0.9300	C53—H53	0.9300
C25—C26	1.399 (4)	C54—C55	1.357 (3)
C25—H25	0.9300	C54—H54	0.9300
C26—C27	1.358 (3)	C55—C56	1.424 (2)
C26—H26	0.9300	C55—H55	0.9300
C27—C28	1.425 (3)	N1—H1A	0.8600
C27—H27	0.9300	N2—H2A	0.8600
C29—C30	1.377 (2)	N4—H4A	0.8600
C29—C34	1.391 (2)	N5—H5A	0.8600
C2—C1—C6	119.44 (19)	C30—C31—H31	120.3
C2—C1—H1	120.3	C32—C31—H31	120.3
C6—C1—H1	120.3	C31—C32—C33	120.71 (18)
C3—C2—C1	121.1 (2)	C31—C32—H32	119.6
C3—C2—H2	119.5	C33—C32—H32	119.6
C1—C2—H2	119.5	C32—C33—C34	119.71 (17)
C4—C3—C2	119.27 (19)	C32—C33—H33	120.1
C4—C3—H3	120.4	C34—C33—H33	120.1
C2—C3—H3	120.4	C33—C34—C29	119.27 (15)
C5—C4—C3	120.3 (2)	C33—C34—N4	124.68 (14)
C5—C4—H4	119.9	C29—C34—N4	115.92 (14)
C3—C4—H4	119.9	N5—C35—N4	116.82 (13)
C4—C5—C6	120.85 (18)	N5—C35—S2	125.39 (11)
C4—C5—H5	119.6	N4—C35—S2	117.79 (11)
C6—C5—H5	119.6	C37—C36—C41	119.01 (13)
C1—C6—C5	118.99 (16)	C37—C36—N5	125.81 (13)
C1—C6—N1	124.94 (16)	C41—C36—N5	115.19 (12)
C5—C6—N1	115.92 (14)	C38—C37—C36	120.32 (14)
N2—C7—N1	117.21 (13)	C38—C37—H37	119.8
N2—C7—S1	125.02 (12)	C36—C37—H37	119.8
N1—C7—S1	117.76 (11)	C39—C38—C37	120.89 (15)
C9—C8—C13	118.98 (13)	C39—C38—H38	119.6
C9—C8—N2	126.00 (13)	C37—C38—H38	119.6
C13—C8—N2	115.01 (12)	C38—C39—C40	119.14 (16)
C10—C9—C8	119.98 (14)	C38—C39—H39	120.4
C10—C9—H9	120.0	C40—C39—H39	120.4
C8—C9—H9	120.0	C41—C40—C39	121.25 (16)
C11—C10—C9	121.11 (15)	C41—C40—H40	119.4
C11—C10—H10	119.4	C39—C40—H40	119.4
C9—C10—H10	119.4	C40—C41—C36	119.38 (13)
C10—C11—C12	119.34 (15)	C40—C41—N6	122.91 (13)
C10—C11—H11	120.3	C36—C41—N6	117.60 (13)
C12—C11—H11	120.3	N6—C42—C43	121.60 (15)
C11—C12—C13	121.02 (15)	N6—C42—H42	119.2
C11—C12—H12	119.5	C43—C42—H42	119.2
C13—C12—H12	119.5	C56—C43—C44	120.31 (14)
C12—C13—C8	119.47 (13)	C56—C43—C42	120.68 (14)
C12—C13—N3	123.33 (13)	C44—C43—C42	119.00 (15)
C8—C13—N3	117.03 (12)	C43—C44—C45	123.47 (16)
N3—C14—C15	121.62 (14)	C43—C44—C49	118.77 (16)
N3—C14—H14	119.2	C45—C44—C49	117.76 (16)
C15—C14—H14	119.2	C46—C45—C44	121.1 (2)
C16—C15—C28	120.45 (14)	C46—C45—H45	119.5
C16—C15—C14	118.51 (14)	C44—C45—H45	119.5
C28—C15—C14	120.97 (14)	C45—C46—C47	120.8 (2)
C15—C16—C17	123.43 (15)	C45—C46—H46	119.6
C15—C16—C21	119.14 (15)	C47—C46—H46	119.6
C17—C16—C21	117.39 (15)	C48—C47—C46	120.2 (2)
C18—C17—C16	121.09 (18)	C48—C47—H47	119.9
C18—C17—H17	119.5	C46—C47—H47	119.9
C16—C17—H17	119.5	C47—C48—C49	121.7 (2)
C17—C18—C19	120.9 (2)	C47—C48—H48	119.1
C17—C18—H18	119.6	C49—C48—H48	119.1
C19—C18—H18	119.6	C50—C49—C48	122.22 (18)
C20—C19—C18	120.17 (19)	C50—C49—C44	119.51 (15)
C20—C19—H19	119.9	C48—C49—C44	118.3 (2)
C18—C19—H19	119.9	C49—C50—C51	122.32 (15)
C19—C20—C21	121.42 (19)	C49—C50—H50	118.8
C19—C20—H20	119.3	C51—C50—H50	118.8
C21—C20—H20	119.3	C50—C51—C52	121.97 (16)
C22—C21—C20	121.45 (17)	C50—C51—C56	119.13 (17)
C22—C21—C16	119.52 (15)	C52—C51—C56	118.88 (16)
C20—C21—C16	119.02 (17)	C53—C52—C51	121.42 (17)
C21—C22—C23	121.73 (15)	C53—C52—H52	119.3
C21—C22—H22	119.1	C51—C52—H52	119.3
C23—C22—H22	119.1	C52—C53—C54	119.96 (18)
C22—C23—C24	121.61 (18)	C52—C53—H53	120.0
C22—C23—C28	119.49 (15)	C54—C53—H53	120.0
C24—C23—C28	118.89 (18)	C55—C54—C53	120.86 (19)
C25—C24—C23	120.5 (2)	C55—C54—H54	119.6
C25—C24—H24	119.7	C53—C54—H54	119.6
C23—C24—H24	119.7	C54—C55—C56	121.67 (16)
C24—C25—C26	120.5 (2)	C54—C55—H55	119.2
C24—C25—H25	119.7	C56—C55—H55	119.2
C26—C25—H25	119.7	C43—C56—C55	123.44 (14)
C27—C26—C25	121.2 (2)	C43—C56—C51	119.30 (15)
C27—C26—H26	119.4	C55—C56—C51	117.07 (15)
C25—C26—H26	119.4	C7—N1—C6	133.57 (13)
C26—C27—C28	120.8 (2)	C7—N1—H1A	113.2
C26—C27—H27	119.6	C6—N1—H1A	113.2
C28—C27—H27	119.6	C7—N2—C8	131.67 (13)
C15—C28—C27	122.69 (16)	C7—N2—H2A	114.2
C15—C28—C23	119.31 (15)	C8—N2—H2A	114.2
C27—C28—C23	117.91 (16)	C14—N3—C13	120.04 (13)
C30—C29—C34	120.22 (17)	C35—N4—C34	132.70 (13)
C30—C29—H29	119.9	C35—N4—H4A	113.6
C34—C29—H29	119.9	C34—N4—H4A	113.6
C31—C30—C29	120.60 (17)	C35—N5—C36	131.68 (12)
C31—C30—H30	119.7	C35—N5—H5A	114.2
C29—C30—H30	119.7	C36—N5—H5A	114.2
C30—C31—C32	119.46 (17)	C42—N6—C41	119.36 (13)
C6—C1—C2—C3	−1.9 (3)	C37—C38—C39—C40	−0.5 (3)
C1—C2—C3—C4	−1.2 (3)	C38—C39—C40—C41	0.9 (3)
C2—C3—C4—C5	2.7 (3)	C39—C40—C41—C36	−0.3 (3)
C3—C4—C5—C6	−1.2 (3)	C39—C40—C41—N6	−176.40 (18)
C2—C1—C6—C5	3.4 (3)	C37—C36—C41—C40	−0.7 (2)
C2—C1—C6—N1	178.75 (19)	N5—C36—C41—C40	178.87 (15)
C4—C5—C6—C1	−1.9 (3)	C37—C36—C41—N6	175.57 (14)
C4—C5—C6—N1	−177.70 (17)	N5—C36—C41—N6	−4.9 (2)
C13—C8—C9—C10	−3.4 (3)	N6—C42—C43—C56	−43.0 (2)
N2—C8—C9—C10	175.63 (16)	N6—C42—C43—C44	136.46 (16)
C8—C9—C10—C11	1.3 (3)	C56—C43—C44—C45	−170.72 (14)
C9—C10—C11—C12	1.3 (3)	C42—C43—C44—C45	9.9 (2)
C10—C11—C12—C13	−1.7 (3)	C56—C43—C44—C49	9.1 (2)
C11—C12—C13—C8	−0.4 (3)	C42—C43—C44—C49	−170.34 (13)
C11—C12—C13—N3	−175.68 (17)	C43—C44—C45—C46	−179.29 (16)
C9—C8—C13—C12	3.0 (2)	C49—C44—C45—C46	0.9 (2)
N2—C8—C13—C12	−176.15 (15)	C44—C45—C46—C47	2.3 (3)
C9—C8—C13—N3	178.55 (15)	C45—C46—C47—C48	−2.8 (3)
N2—C8—C13—N3	−0.6 (2)	C46—C47—C48—C49	0.0 (3)
N3—C14—C15—C16	131.51 (17)	C47—C48—C49—C50	−176.09 (18)
N3—C14—C15—C28	−45.5 (2)	C47—C48—C49—C44	3.2 (3)
C28—C15—C16—C17	−175.64 (14)	C43—C44—C49—C50	−4.1 (2)
C14—C15—C16—C17	7.4 (2)	C45—C44—C49—C50	175.73 (15)
C28—C15—C16—C21	6.8 (2)	C43—C44—C49—C48	176.64 (15)
C14—C15—C16—C21	−170.17 (13)	C45—C44—C49—C48	−3.5 (2)
C15—C16—C17—C18	−176.45 (16)	C48—C49—C50—C51	176.32 (16)
C21—C16—C17—C18	1.1 (2)	C44—C49—C50—C51	−2.9 (2)
C16—C17—C18—C19	0.7 (3)	C49—C50—C51—C52	−173.56 (15)
C17—C18—C19—C20	−1.8 (3)	C49—C50—C51—C56	4.9 (2)
C18—C19—C20—C21	0.8 (3)	C50—C51—C52—C53	174.92 (17)
C19—C20—C21—C22	179.76 (17)	C56—C51—C52—C53	−3.5 (2)
C19—C20—C21—C16	1.0 (3)	C51—C52—C53—C54	0.5 (3)
C15—C16—C21—C22	−3.1 (2)	C52—C53—C54—C55	2.6 (3)
C17—C16—C21—C22	179.26 (14)	C53—C54—C55—C56	−2.4 (3)
C15—C16—C21—C20	175.70 (14)	C44—C43—C56—C55	167.66 (14)
C17—C16—C21—C20	−2.0 (2)	C42—C43—C56—C55	−12.9 (2)
C20—C21—C22—C23	179.24 (15)	C44—C43—C56—C51	−7.2 (2)
C16—C21—C22—C23	−2.0 (2)	C42—C43—C56—C51	172.21 (13)
C21—C22—C23—C24	−175.56 (16)	C54—C55—C56—C43	−175.61 (15)
C21—C22—C23—C28	3.3 (2)	C54—C55—C56—C51	−0.6 (2)
C22—C23—C24—C25	176.57 (19)	C50—C51—C56—C43	0.2 (2)
C28—C23—C24—C25	−2.3 (3)	C52—C51—C56—C43	178.72 (14)
C23—C24—C25—C26	−0.1 (4)	C50—C51—C56—C55	−174.95 (14)
C24—C25—C26—C27	2.2 (4)	C52—C51—C56—C55	3.5 (2)
C25—C26—C27—C28	−1.7 (3)	N2—C7—N1—C6	9.4 (3)
C16—C15—C28—C27	170.93 (15)	S1—C7—N1—C6	−171.10 (15)
C14—C15—C28—C27	−12.2 (2)	C1—C6—N1—C7	26.5 (3)
C16—C15—C28—C23	−5.6 (2)	C5—C6—N1—C7	−157.95 (18)
C14—C15—C28—C23	171.36 (14)	N1—C7—N2—C8	−166.81 (16)
C26—C27—C28—C15	−177.34 (18)	S1—C7—N2—C8	13.8 (3)
C26—C27—C28—C23	−0.8 (3)	C9—C8—N2—C7	−14.2 (3)
C22—C23—C28—C15	0.5 (2)	C13—C8—N2—C7	164.89 (16)
C24—C23—C28—C15	179.40 (15)	C15—C14—N3—C13	177.32 (14)
C22—C23—C28—C27	−176.18 (15)	C12—C13—N3—C14	−34.9 (2)
C24—C23—C28—C27	2.7 (2)	C8—C13—N3—C14	149.78 (16)
C34—C29—C30—C31	1.0 (3)	N5—C35—N4—C34	−14.2 (3)
C29—C30—C31—C32	−0.7 (3)	S2—C35—N4—C34	165.96 (15)
C30—C31—C32—C33	−0.7 (3)	C33—C34—N4—C35	−25.0 (3)
C31—C32—C33—C34	1.8 (3)	C29—C34—N4—C35	159.31 (17)
C32—C33—C34—C29	−1.4 (3)	N4—C35—N5—C36	167.90 (15)
C32—C33—C34—N4	−177.02 (17)	S2—C35—N5—C36	−12.3 (3)
C30—C29—C34—C33	0.1 (3)	C37—C36—N5—C35	18.4 (3)
C30—C29—C34—N4	176.05 (16)	C41—C36—N5—C35	−161.10 (16)
C41—C36—C37—C38	1.1 (2)	C43—C42—N6—C41	174.85 (14)
N5—C36—C37—C38	−178.38 (15)	C40—C41—N6—C42	−36.1 (2)
C36—C37—C38—C39	−0.5 (3)	C36—C41—N6—C42	147.81 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.55	3.399 (2)	169
N2—H2A···N3	0.86	2.22	2.650 (2)	111
N4—H4A···S2ii	0.86	2.63	3.475 (1)	169
N5—H5A···N6	0.86	2.25	2.666 (2)	110

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.55	3.399 (2)	169
N2—H2A⋯N3	0.86	2.22	2.650 (2)	111
N4—H4A⋯S2ii	0.86	2.63	3.475 (1)	169
N5—H5A⋯N6	0.86	2.25	2.666 (2)	110

Symmetry codes: (i) ; (ii) .