1-Benzoyl-3-methyl-3-pentyl-thio-urea.

Two independent mol-ecules comprise the asymmetric unit of the title compound, C(14)H(20)N(2)OS. These differ in the relative orientations of the pentyl chains [C-C-C-C torsion angles = -176.7 (3) and 176.4 (3)°]. Significant twists are evident in each mol-ecule, the dihedral angles formed between the thio-urea and amide residues being 53.47 (17) and 55.81 (17)°. In the crystal, each mol-ecule self-associates via a centrosymmetric eight-membered {⋯HNC=S}(2) synthon, and these are connected into a supra-molecular chain along [110] via C-H⋯O contacts. Disorder is noted for one of the independent mol-ecules in that two orientations (50:50) were resolved for its benzene ring.

Related literature

For the coordination potental of thio­urea derivatives, see: Pisiewicz et al. (2010 ▶). For pharmaceutical applications of thio­ruea deriavives, see: Venkatachalam et al. (2004 ▶); Bruce et al. (2007 ▶). For applications of thio­urea derivatives in catalysis, see: Gunasekaran et al. (2010 ▶, 2011 ▶). For closely related structures, see: Gunasekaran et al. (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

C14H20N2OS

M = 264.38

Triclinic,

a = 9.0992 (6) Å

b = 10.5297 (6) Å

c = 16.4038 (8) Å

α = 75.784 (5)°

β = 77.831 (5)°

γ = 82.877 (5)°

V = 1484.98 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.853, T max = 1.000

11884 measured reflections

6585 independent reflections

3555 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.184

S = 1.03

6585 reflections

321 parameters

37 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and QMOL (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013365/hb5837sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013365/hb5837Isup2.hkl

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

C14H20N2OS	Z = 4
Mr = 264.38	F(000) = 568
Triclinic, P1	Dx = 1.183 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0992 (6) Å	Cell parameters from 2904 reflections
b = 10.5297 (6) Å	θ = 2.3–29.3°
c = 16.4038 (8) Å	µ = 0.21 mm−1
α = 75.784 (5)°	T = 295 K
β = 77.831 (5)°	Block, colourless
γ = 82.877 (5)°	0.25 × 0.20 × 0.15 mm
V = 1484.98 (15) Å3

Agilent Supernova Dual diffractometer with an Atlas detector	6585 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3555 reflections with I > 2σ(I)
Mirror	Rint = 0.034
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→13
Tmin = 0.853, Tmax = 1.000	l = −21→17
11884 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.071P)2 + 0.1338P] where P = (Fo2 + 2Fc2)/3
6585 reflections	(Δ/σ)max = 0.001
321 parameters	Δρmax = 0.33 e Å−3
37 restraints	Δρmin = −0.27 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	Occ. (<1)
S1	0.61942 (10)	0.45168 (7)	0.37694 (5)	0.0643 (3)
S2	0.53313 (10)	1.00478 (8)	0.86780 (5)	0.0709 (3)
O1	0.9407 (2)	0.6383 (2)	0.43989 (13)	0.0707 (6)
O2	0.9060 (2)	1.1826 (2)	0.88476 (13)	0.0753 (6)
N1	0.6894 (3)	0.6324 (2)	0.44660 (14)	0.0531 (6)
H1	0.5983	0.6498	0.4746	0.064*
N2	0.7833 (3)	0.6553 (2)	0.30138 (13)	0.0522 (6)
N3	0.6572 (3)	1.1566 (2)	0.93652 (13)	0.0548 (6)
H3	0.5849	1.1562	0.9816	0.066*
N4	0.6452 (2)	1.2346 (2)	0.79196 (13)	0.0504 (5)
C1	0.8832 (4)	0.6575 (3)	0.61411 (19)	0.0687 (9)
H1A	0.9727	0.6093	0.5978	0.082*
C2	0.8564 (5)	0.6965 (3)	0.6908 (2)	0.0818 (10)
H2	0.9271	0.6727	0.7265	0.098*
C3	0.7272 (5)	0.7696 (3)	0.7145 (2)	0.0810 (11)
H3A	0.7106	0.7961	0.7660	0.097*
C4	0.6215 (4)	0.8042 (3)	0.6629 (2)	0.0735 (9)
H4A	0.5337	0.8548	0.6789	0.088*
C5	0.6465 (4)	0.7633 (3)	0.58688 (18)	0.0616 (8)
H5	0.5743	0.7854	0.5522	0.074*
C6	0.7779 (3)	0.6897 (3)	0.56196 (17)	0.0531 (7)
C7	0.8127 (3)	0.6516 (3)	0.47817 (17)	0.0537 (7)
C8	0.7042 (3)	0.5864 (2)	0.37203 (16)	0.0492 (6)
C9	0.8225 (4)	0.7902 (3)	0.29168 (19)	0.0658 (8)
H9A	0.7595	0.8278	0.3359	0.099*
H9B	0.8073	0.8420	0.2367	0.099*
H9C	0.9263	0.7888	0.2960	0.099*
C10	0.8343 (3)	0.6011 (3)	0.22507 (17)	0.0571 (7)
H10A	0.8415	0.5060	0.2427	0.069*
H10B	0.9346	0.6280	0.1982	0.069*
C11	0.7337 (3)	0.6426 (3)	0.16005 (17)	0.0624 (8)
H11A	0.7196	0.7377	0.1454	0.075*
H11B	0.6357	0.6088	0.1848	0.075*
C12	0.7986 (4)	0.5931 (3)	0.07880 (18)	0.0645 (8)
H12A	0.8938	0.6311	0.0524	0.077*
H12B	0.8189	0.4985	0.0942	0.077*
C13	0.6965 (4)	0.6257 (4)	0.0148 (2)	0.0817 (10)
H13A	0.6789	0.7204	−0.0020	0.098*
H13B	0.6002	0.5900	0.0417	0.098*
C14	0.7584 (5)	0.5731 (4)	−0.0640 (2)	0.1030 (14)
H14A	0.6881	0.5970	−0.1024	0.154*
H14B	0.7741	0.4792	−0.0480	0.154*
H14C	0.8526	0.6097	−0.0918	0.154*
C15	0.9809 (9)	1.1289 (13)	1.0465 (5)	0.0735 (18)	0.50
H15	1.0559	1.1012	1.0051	0.088*	0.50
C16	1.0117 (6)	1.1274 (10)	1.1263 (5)	0.089 (2)	0.50
H16	1.1074	1.0987	1.1382	0.107*	0.50
C17	0.8995 (7)	1.1687 (8)	1.1882 (3)	0.087 (3)	0.50
H17	0.9202	1.1677	1.2415	0.104*	0.50
C18	0.7565 (6)	1.2116 (8)	1.1703 (4)	0.082 (2)	0.50
H18	0.6815	1.2393	1.2117	0.099*	0.50
C19	0.7257 (8)	1.2131 (11)	1.0906 (5)	0.0648 (19)	0.50
H19	0.6300	1.2418	1.0787	0.078*	0.50
C20	0.8379 (10)	1.1718 (14)	1.0287 (4)	0.0552 (16)	0.50
C15'	0.9290 (9)	1.1414 (12)	1.0646 (5)	0.0735 (18)	0.50
H15'	1.0083	1.1017	1.0314	0.088*	0.50
C16'	0.9421 (7)	1.1526 (10)	1.1454 (5)	0.089 (2)	0.50
H16'	1.0301	1.1204	1.1662	0.107*	0.50
C17'	0.8235 (8)	1.2120 (8)	1.1952 (3)	0.087 (3)	0.50
H17'	0.8323	1.2195	1.2492	0.104*	0.50
C18'	0.6918 (7)	1.2602 (8)	1.1641 (4)	0.082 (2)	0.50
H18'	0.6125	1.2999	1.1973	0.099*	0.50
C19'	0.6788 (8)	1.2490 (11)	1.0833 (5)	0.0648 (19)	0.50
H19'	0.5907	1.2812	1.0625	0.078*	0.50
C20'	0.7973 (11)	1.1896 (13)	1.0335 (4)	0.0552 (16)	0.50
C21	0.8010 (4)	1.1734 (3)	0.94459 (18)	0.0573 (7)
C22	0.6179 (3)	1.1403 (3)	0.86181 (16)	0.0498 (6)
C23	0.7007 (4)	1.3610 (3)	0.78851 (19)	0.0654 (8)
H23A	0.6846	1.3758	0.8453	0.098*
H23B	0.6474	1.4302	0.7534	0.098*
H23C	0.8065	1.3599	0.7645	0.098*
C24	0.6123 (3)	1.2216 (3)	0.71090 (17)	0.0564 (7)
H24A	0.5828	1.3080	0.6787	0.068*
H24B	0.5274	1.1682	0.7230	0.068*
C25	0.7425 (3)	1.1613 (3)	0.65679 (17)	0.0612 (8)
H25A	0.7716	1.0741	0.6880	0.073*
H25B	0.8280	1.2142	0.6442	0.073*
C26	0.7007 (4)	1.1520 (3)	0.57313 (18)	0.0655 (8)
H26A	0.6110	1.1041	0.5864	0.079*
H26B	0.6764	1.2399	0.5412	0.079*
C27	0.8234 (4)	1.0852 (3)	0.51769 (19)	0.0768 (9)
H27A	0.8489	0.9977	0.5499	0.092*
H27B	0.9126	1.1339	0.5036	0.092*
C28	0.7804 (5)	1.0744 (4)	0.4357 (2)	0.0996 (13)
H28A	0.8630	1.0315	0.4031	0.149*
H28B	0.7569	1.1607	0.4029	0.149*
H28C	0.6938	1.0242	0.4491	0.149*

	U11	U22	U33	U12	U13	U23
S1	0.0813 (6)	0.0575 (4)	0.0548 (5)	−0.0222 (4)	−0.0078 (4)	−0.0099 (3)
S2	0.0970 (7)	0.0662 (5)	0.0537 (5)	−0.0357 (5)	−0.0040 (4)	−0.0159 (4)
O1	0.0542 (14)	0.1030 (16)	0.0591 (13)	−0.0065 (12)	−0.0091 (11)	−0.0271 (12)
O2	0.0600 (14)	0.1055 (17)	0.0560 (13)	−0.0133 (12)	−0.0061 (11)	−0.0105 (12)
N1	0.0473 (14)	0.0685 (14)	0.0470 (13)	−0.0106 (11)	−0.0049 (10)	−0.0201 (11)
N2	0.0558 (14)	0.0595 (13)	0.0433 (12)	−0.0143 (11)	−0.0056 (10)	−0.0136 (11)
N3	0.0578 (15)	0.0684 (14)	0.0399 (12)	−0.0169 (12)	−0.0009 (10)	−0.0165 (11)
N4	0.0537 (14)	0.0545 (13)	0.0438 (12)	−0.0105 (11)	−0.0081 (10)	−0.0103 (10)
C1	0.079 (2)	0.0736 (19)	0.0589 (19)	−0.0030 (17)	−0.0228 (17)	−0.0192 (16)
C2	0.115 (3)	0.081 (2)	0.059 (2)	−0.011 (2)	−0.036 (2)	−0.0166 (18)
C3	0.120 (3)	0.072 (2)	0.0526 (19)	−0.020 (2)	−0.006 (2)	−0.0202 (17)
C4	0.082 (2)	0.068 (2)	0.067 (2)	−0.0166 (18)	0.0057 (19)	−0.0202 (17)
C5	0.067 (2)	0.0676 (18)	0.0528 (17)	−0.0205 (16)	−0.0036 (15)	−0.0167 (14)
C6	0.0601 (19)	0.0543 (15)	0.0464 (15)	−0.0152 (14)	−0.0063 (14)	−0.0120 (13)
C7	0.0560 (19)	0.0601 (17)	0.0463 (15)	−0.0085 (14)	−0.0105 (14)	−0.0116 (13)
C8	0.0487 (16)	0.0552 (15)	0.0455 (15)	−0.0074 (13)	−0.0100 (12)	−0.0115 (12)
C9	0.074 (2)	0.0660 (18)	0.0574 (18)	−0.0282 (16)	−0.0030 (15)	−0.0107 (15)
C10	0.0505 (17)	0.0713 (18)	0.0497 (16)	−0.0064 (14)	−0.0026 (13)	−0.0190 (14)
C11	0.062 (2)	0.0771 (19)	0.0505 (17)	−0.0022 (16)	−0.0114 (14)	−0.0184 (15)
C12	0.075 (2)	0.0686 (18)	0.0514 (17)	−0.0088 (16)	−0.0110 (15)	−0.0160 (14)
C13	0.095 (3)	0.094 (2)	0.062 (2)	0.000 (2)	−0.0252 (19)	−0.0226 (18)
C14	0.157 (4)	0.100 (3)	0.062 (2)	−0.013 (3)	−0.034 (2)	−0.025 (2)
C15	0.085 (6)	0.069 (3)	0.074 (3)	−0.011 (4)	−0.028 (4)	−0.016 (3)
C16	0.110 (6)	0.086 (4)	0.084 (4)	−0.017 (4)	−0.049 (5)	−0.011 (3)
C17	0.108 (7)	0.101 (5)	0.061 (3)	−0.042 (5)	−0.030 (4)	−0.008 (3)
C18	0.096 (6)	0.097 (6)	0.060 (3)	−0.043 (4)	0.000 (3)	−0.023 (3)
C19	0.066 (5)	0.077 (5)	0.053 (2)	−0.026 (4)	−0.007 (2)	−0.012 (3)
C20	0.059 (5)	0.055 (3)	0.0513 (19)	−0.017 (3)	−0.014 (2)	−0.0020 (16)
C15'	0.085 (6)	0.069 (3)	0.074 (3)	−0.011 (4)	−0.028 (4)	−0.016 (3)
C16'	0.110 (6)	0.086 (4)	0.084 (4)	−0.017 (4)	−0.049 (5)	−0.011 (3)
C17'	0.108 (7)	0.101 (5)	0.061 (3)	−0.042 (5)	−0.030 (4)	−0.008 (3)
C18'	0.096 (6)	0.097 (6)	0.060 (3)	−0.043 (4)	0.000 (3)	−0.023 (3)
C19'	0.066 (5)	0.077 (5)	0.053 (2)	−0.026 (4)	−0.007 (2)	−0.012 (3)
C20'	0.059 (5)	0.055 (3)	0.0513 (19)	−0.017 (3)	−0.014 (2)	−0.0020 (16)
C21	0.069 (2)	0.0562 (16)	0.0464 (16)	−0.0165 (15)	−0.0122 (15)	−0.0049 (13)
C22	0.0520 (17)	0.0552 (15)	0.0444 (15)	−0.0106 (13)	−0.0048 (12)	−0.0158 (13)
C23	0.077 (2)	0.0569 (16)	0.0643 (19)	−0.0220 (15)	−0.0176 (16)	−0.0047 (15)
C24	0.0570 (18)	0.0629 (17)	0.0504 (16)	−0.0062 (14)	−0.0157 (14)	−0.0096 (13)
C25	0.0575 (19)	0.0749 (19)	0.0518 (17)	−0.0068 (15)	−0.0125 (14)	−0.0126 (15)
C26	0.072 (2)	0.0721 (19)	0.0501 (17)	−0.0020 (16)	−0.0134 (15)	−0.0093 (15)
C27	0.083 (2)	0.088 (2)	0.0565 (19)	−0.0053 (19)	−0.0004 (17)	−0.0212 (17)
C28	0.142 (4)	0.101 (3)	0.053 (2)	0.013 (3)	−0.015 (2)	−0.0249 (19)

S1—C8	1.674 (3)	C14—H14B	0.9600
S2—C22	1.677 (3)	C14—H14C	0.9600
O1—C7	1.210 (3)	C15—C16	1.3900
O2—C21	1.211 (3)	C15—C20	1.3900
N1—C7	1.387 (3)	C15—H15	0.9300
N1—C8	1.398 (3)	C16—C17	1.3900
N1—H1	0.8800	C16—H16	0.9300
N2—C8	1.324 (3)	C17—C18	1.3900
N2—C10	1.466 (3)	C17—H17	0.9300
N2—C9	1.470 (3)	C18—C19	1.3900
N3—C21	1.379 (4)	C18—H18	0.9300
N3—C22	1.401 (3)	C19—C20	1.3900
N3—H3	0.8800	C19—H19	0.9300
N4—C22	1.320 (3)	C20—C21	1.483 (5)
N4—C24	1.464 (3)	C15'—C16'	1.3900
N4—C23	1.466 (3)	C15'—C20'	1.3900
C1—C6	1.374 (4)	C15'—H15'	0.9300
C1—C2	1.383 (4)	C16'—C17'	1.3900
C1—H1A	0.9300	C16'—H16'	0.9300
C2—C3	1.362 (5)	C17'—C18'	1.3900
C2—H2	0.9300	C17'—H17'	0.9300
C3—C4	1.371 (5)	C18'—C19'	1.3900
C3—H3A	0.9300	C18'—H18'	0.9300
C4—C5	1.383 (4)	C19'—C20'	1.3900
C4—H4A	0.9300	C19'—H19'	0.9300
C5—C6	1.385 (4)	C20'—C21	1.503 (5)
C5—H5	0.9300	C23—H23A	0.9600
C6—C7	1.485 (4)	C23—H23B	0.9600
C9—H9A	0.9600	C23—H23C	0.9600
C9—H9B	0.9600	C24—C25	1.498 (4)
C9—H9C	0.9600	C24—H24A	0.9700
C10—C11	1.500 (4)	C24—H24B	0.9700
C10—H10A	0.9700	C25—C26	1.528 (4)
C10—H10B	0.9700	C25—H25A	0.9700
C11—C12	1.526 (4)	C25—H25B	0.9700
C11—H11A	0.9700	C26—C27	1.503 (4)
C11—H11B	0.9700	C26—H26A	0.9700
C12—C13	1.495 (4)	C26—H26B	0.9700
C12—H12A	0.9700	C27—C28	1.511 (5)
C12—H12B	0.9700	C27—H27A	0.9700
C13—C14	1.503 (4)	C27—H27B	0.9700
C13—H13A	0.9700	C28—H28A	0.9600
C13—H13B	0.9700	C28—H28B	0.9600
C14—H14A	0.9600	C28—H28C	0.9600
C7—N1—C8	122.5 (2)	C15—C16—H16	120.0
C7—N1—H1	118.8	C16—C17—C18	120.0
C8—N1—H1	118.8	C16—C17—H17	120.0
C8—N2—C10	121.0 (2)	C18—C17—H17	120.0
C8—N2—C9	123.9 (2)	C17—C18—C19	120.0
C10—N2—C9	115.1 (2)	C17—C18—H18	120.0
C21—N3—C22	124.8 (2)	C19—C18—H18	120.0
C21—N3—H3	117.6	C20—C19—C18	120.0
C22—N3—H3	117.6	C20—C19—H19	120.0
C22—N4—C24	120.8 (2)	C18—C19—H19	120.0
C22—N4—C23	124.7 (2)	C19—C20—C15	120.0
C24—N4—C23	114.4 (2)	C19—C20—C21	118.7 (5)
C6—C1—C2	120.2 (3)	C15—C20—C21	121.3 (5)
C6—C1—H1A	119.9	C16'—C15'—C20'	120.0
C2—C1—H1A	119.9	C16'—C15'—H15'	120.0
C3—C2—C1	120.4 (3)	C20'—C15'—H15'	120.0
C3—C2—H2	119.8	C15'—C16'—C17'	120.0
C1—C2—H2	119.8	C15'—C16'—H16'	120.0
C2—C3—C4	120.4 (3)	C17'—C16'—H16'	120.0
C2—C3—H3A	119.8	C18'—C17'—C16'	120.0
C4—C3—H3A	119.8	C18'—C17'—H17'	120.0
C3—C4—C5	119.4 (3)	C16'—C17'—H17'	120.0
C3—C4—H4A	120.3	C19'—C18'—C17'	120.0
C5—C4—H4A	120.3	C19'—C18'—H18'	120.0
C6—C5—C4	120.7 (3)	C17'—C18'—H18'	120.0
C6—C5—H5	119.7	C18'—C19'—C20'	120.0
C4—C5—H5	119.7	C18'—C19'—H19'	120.0
C1—C6—C5	119.0 (3)	C20'—C19'—H19'	120.0
C1—C6—C7	118.9 (3)	C19'—C20'—C15'	120.0
C5—C6—C7	122.0 (3)	C19'—C20'—C21	126.0 (6)
O1—C7—N1	122.1 (3)	C15'—C20'—C21	114.0 (6)
O1—C7—C6	122.1 (3)	O2—C21—N3	122.2 (3)
N1—C7—C6	115.8 (3)	O2—C21—C20	116.0 (5)
N2—C8—N1	116.8 (2)	N3—C21—C20	121.6 (5)
N2—C8—S1	124.5 (2)	O2—C21—C20'	128.5 (5)
N1—C8—S1	118.72 (19)	N3—C21—C20'	109.1 (5)
N2—C9—H9A	109.5	C20—C21—C20'	15.2 (6)
N2—C9—H9B	109.5	N4—C22—N3	117.9 (2)
H9A—C9—H9B	109.5	N4—C22—S2	124.2 (2)
N2—C9—H9C	109.5	N3—C22—S2	117.86 (19)
H9A—C9—H9C	109.5	N4—C23—H23A	109.5
H9B—C9—H9C	109.5	N4—C23—H23B	109.5
N2—C10—C11	114.3 (2)	H23A—C23—H23B	109.5
N2—C10—H10A	108.7	N4—C23—H23C	109.5
C11—C10—H10A	108.7	H23A—C23—H23C	109.5
N2—C10—H10B	108.7	H23B—C23—H23C	109.5
C11—C10—H10B	108.7	N4—C24—C25	113.6 (2)
H10A—C10—H10B	107.6	N4—C24—H24A	108.9
C10—C11—C12	112.1 (2)	C25—C24—H24A	108.9
C10—C11—H11A	109.2	N4—C24—H24B	108.9
C12—C11—H11A	109.2	C25—C24—H24B	108.9
C10—C11—H11B	109.2	H24A—C24—H24B	107.7
C12—C11—H11B	109.2	C24—C25—C26	110.7 (2)
H11A—C11—H11B	107.9	C24—C25—H25A	109.5
C13—C12—C11	113.5 (3)	C26—C25—H25A	109.5
C13—C12—H12A	108.9	C24—C25—H25B	109.5
C11—C12—H12A	108.9	C26—C25—H25B	109.5
C13—C12—H12B	108.9	H25A—C25—H25B	108.1
C11—C12—H12B	108.9	C27—C26—C25	113.6 (3)
H12A—C12—H12B	107.7	C27—C26—H26A	108.8
C12—C13—C14	113.4 (3)	C25—C26—H26A	108.8
C12—C13—H13A	108.9	C27—C26—H26B	108.8
C14—C13—H13A	108.9	C25—C26—H26B	108.8
C12—C13—H13B	108.9	H26A—C26—H26B	107.7
C14—C13—H13B	108.9	C26—C27—C28	113.3 (3)
H13A—C13—H13B	107.7	C26—C27—H27A	108.9
C13—C14—H14A	109.5	C28—C27—H27A	108.9
C13—C14—H14B	109.5	C26—C27—H27B	108.9
H14A—C14—H14B	109.5	C28—C27—H27B	108.9
C13—C14—H14C	109.5	H27A—C27—H27B	107.7
H14A—C14—H14C	109.5	C27—C28—H28A	109.5
H14B—C14—H14C	109.5	C27—C28—H28B	109.5
C16—C15—C20	120.0	H28A—C28—H28B	109.5
C16—C15—H15	120.0	C27—C28—H28C	109.5
C20—C15—H15	120.0	H28A—C28—H28C	109.5
C17—C16—C15	120.0	H28B—C28—H28C	109.5
C17—C16—H16	120.0
C6—C1—C2—C3	−1.4 (5)	C15'—C16'—C17'—C18'	0.0
C1—C2—C3—C4	0.6 (5)	C16'—C17'—C18'—C19'	0.0
C2—C3—C4—C5	0.6 (5)	C17'—C18'—C19'—C20'	0.0
C3—C4—C5—C6	−1.0 (5)	C18'—C19'—C20'—C15'	0.0
C2—C1—C6—C5	1.0 (4)	C18'—C19'—C20'—C21	−178.4 (12)
C2—C1—C6—C7	177.3 (3)	C16'—C15'—C20'—C19'	0.0
C4—C5—C6—C1	0.2 (4)	C16'—C15'—C20'—C21	178.6 (10)
C4—C5—C6—C7	−175.9 (3)	C22—N3—C21—O2	4.2 (4)
C8—N1—C7—O1	5.1 (4)	C22—N3—C21—C20	−171.5 (6)
C8—N1—C7—C6	−174.9 (2)	C22—N3—C21—C20'	179.1 (6)
C1—C6—C7—O1	−27.5 (4)	C19—C20—C21—O2	154.8 (5)
C5—C6—C7—O1	148.7 (3)	C15—C20—C21—O2	−25.8 (9)
C1—C6—C7—N1	152.6 (3)	C19—C20—C21—N3	−29.3 (10)
C5—C6—C7—N1	−31.3 (4)	C15—C20—C21—N3	150.1 (5)
C10—N2—C8—N1	166.1 (2)	C19—C20—C21—C20'	7(4)
C9—N2—C8—N1	−15.9 (4)	C15—C20—C21—C20'	−174 (5)
C10—N2—C8—S1	−15.1 (4)	C19'—C20'—C21—O2	141.8 (6)
C9—N2—C8—S1	162.9 (2)	C15'—C20'—C21—O2	−36.7 (9)
C7—N1—C8—N2	−56.8 (3)	C19'—C20'—C21—N3	−32.8 (10)
C7—N1—C8—S1	124.4 (2)	C15'—C20'—C21—N3	148.7 (5)
C8—N2—C10—C11	96.6 (3)	C19'—C20'—C21—C20	179 (5)
C9—N2—C10—C11	−81.5 (3)	C15'—C20'—C21—C20	1(4)
N2—C10—C11—C12	175.1 (2)	C24—N4—C22—N3	177.6 (2)
C10—C11—C12—C13	176.4 (3)	C23—N4—C22—N3	−6.0 (4)
C11—C12—C13—C14	−178.2 (3)	C24—N4—C22—S2	−4.8 (4)
C20—C15—C16—C17	0.0	C23—N4—C22—S2	171.5 (2)
C15—C16—C17—C18	0.0	C21—N3—C22—N4	−59.2 (4)
C16—C17—C18—C19	0.0	C21—N3—C22—S2	123.0 (3)
C17—C18—C19—C20	0.0	C22—N4—C24—C25	−91.2 (3)
C18—C19—C20—C15	0.0	C23—N4—C24—C25	92.1 (3)
C18—C19—C20—C21	179.4 (11)	N4—C24—C25—C26	−179.5 (2)
C16—C15—C20—C19	0.0	C24—C25—C26—C27	−176.7 (3)
C16—C15—C20—C21	−179.4 (11)	C25—C26—C27—C28	179.1 (3)
C20'—C15'—C16'—C17'	0.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.88	2.87	3.604 (2)	143
N3—H3···S2ii	0.88	2.72	3.449 (2)	141
C10—H10b···O2iii	0.97	2.55	3.397 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.88	2.87	3.604 (2)	143
N3—H3⋯S2ii	0.88	2.72	3.449 (2)	141
C10—H10b⋯O2iii	0.97	2.55	3.397 (4)	146

Symmetry codes: (i) ; (ii) ; (iii) .