1-Benzoyl-3,3-bis-(propan-2-yl)thio-urea.

Two independent thio-urea derivatives comprise the asymmetric unit of the title compound, C(14)H(20)N(2)OS. The major difference between the mol-ecules relates to a twist in the relative orientation of the benzene rings [torsion angles = 4.5 (2) and -19.9 (2)° for the two independent mol-ecules]. The thio-carbonyl and carbonyl groups lie to opposite sides of the mol-ecule as there are twists about the central N-S bond [torsion angles = 83.90 (15) and 81.77 (15)°]. Supra-molecular chains extending parallel to [101] with a stepped topology and mediated by N-H⋯O hydrogen bonding feature in the crystal structure. C-H⋯O and C-H⋯π inter-actions are also present.

Related literature

For the biological activity of thio­urea derivatives, see: Venkatachalam et al. (2004 ▶); Yuan et al. (2001 ▶); Zhou et al. (2004 ▶). For the use of ruthenium(III) complexes of thio­ureas as catalysts, see: Gunasekaran & Karvembru (2010 ▶). For additional structural analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C14H20N2OS

M = 264.38

Monoclinic,

a = 14.8072 (10) Å

b = 13.5832 (10) Å

c = 14.9168 (11) Å

β = 97.635 (1)°

V = 2973.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.40 × 0.25 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.921, T max = 0.990

27965 measured reflections

6833 independent reflections

5254 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.02

6833 reflections

341 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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/S1600536810028862/ez2225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028862/ez2225Isup2.hkl

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

C14H20N2OS	F(000) = 1136
Mr = 264.38	Dx = 1.181 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5840 reflections
a = 14.8072 (10) Å	θ = 2.4–28.1°
b = 13.5832 (10) Å	µ = 0.21 mm−1
c = 14.9168 (11) Å	T = 100 K
β = 97.635 (1)°	Prism, colourless
V = 2973.6 (4) Å3	0.40 × 0.25 × 0.05 mm
Z = 8

Bruker SMART APEX diffractometer	6833 independent reflections
Radiation source: fine-focus sealed tube	5254 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.921, Tmax = 0.990	k = −17→17
27965 measured reflections	l = −19→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.4491P] where P = (Fo2 + 2Fc2)/3
6833 reflections	(Δ/σ)max = 0.001
341 parameters	Δρmax = 0.32 e Å−3
2 restraints	Δρmin = −0.22 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	0.75721 (3)	0.79767 (3)	0.15341 (3)	0.01907 (10)
S2	1.24751 (3)	0.74064 (3)	0.16642 (3)	0.01868 (10)
O1	0.97620 (7)	0.75101 (8)	0.11338 (7)	0.0217 (2)
O2	1.20465 (7)	0.80331 (8)	0.38108 (7)	0.0198 (2)
N1	0.84390 (8)	0.70403 (9)	0.03311 (8)	0.0135 (2)
H1	0.8091 (11)	0.7049 (14)	−0.0167 (8)	0.033 (5)*
N2	0.80562 (8)	0.60687 (9)	0.15068 (8)	0.0160 (3)
N3	1.11221 (8)	0.81185 (9)	0.24783 (8)	0.0136 (3)
H3	1.0643 (9)	0.7908 (14)	0.2154 (12)	0.037 (6)*
N4	1.19743 (9)	0.92929 (9)	0.18289 (8)	0.0172 (3)
C1	0.97327 (10)	0.74376 (10)	−0.04643 (10)	0.0150 (3)
C2	1.06667 (10)	0.76249 (11)	−0.03733 (11)	0.0191 (3)
H2	1.0994	0.7740	0.0209	0.023*
C3	1.11180 (11)	0.76431 (11)	−0.11299 (11)	0.0213 (3)
H3A	1.1754	0.7772	−0.1063	0.026*
C4	1.06483 (11)	0.74753 (11)	−0.19821 (11)	0.0202 (3)
H4	1.0961	0.7478	−0.2498	0.024*
C5	0.97160 (10)	0.73027 (11)	−0.20766 (10)	0.0183 (3)
H5	0.9390	0.7197	−0.2662	0.022*
C6	0.92549 (10)	0.72824 (10)	−0.13246 (10)	0.0164 (3)
H6	0.8617	0.7163	−0.1395	0.020*
C7	0.93123 (10)	0.73556 (10)	0.03927 (10)	0.0153 (3)
C8	0.80264 (10)	0.69632 (10)	0.11469 (9)	0.0142 (3)
C9	0.83729 (11)	0.51575 (10)	0.10756 (10)	0.0188 (3)
H9	0.8239	0.4604	0.1480	0.023*
C10	0.93975 (11)	0.51274 (12)	0.10634 (12)	0.0270 (4)
H10A	0.9708	0.5373	0.1641	0.041*
H10B	0.9557	0.5542	0.0570	0.041*
H10C	0.9588	0.4448	0.0972	0.041*
C11	0.78275 (13)	0.49311 (12)	0.01598 (11)	0.0295 (4)
H11A	0.7175	0.4995	0.0203	0.044*
H11B	0.7959	0.4258	−0.0020	0.044*
H11C	0.7997	0.5395	−0.0292	0.044*
C12	0.77042 (12)	0.59103 (12)	0.23844 (11)	0.0252 (4)
H12	0.7585	0.6574	0.2633	0.030*
C13	0.84165 (14)	0.54090 (13)	0.30663 (11)	0.0340 (4)
H13A	0.8201	0.5393	0.3660	0.051*
H13B	0.8990	0.5777	0.3111	0.051*
H13C	0.8516	0.4735	0.2867	0.051*
C14	0.68014 (13)	0.53676 (13)	0.22384 (14)	0.0364 (5)
H14A	0.6374	0.5727	0.1798	0.055*
H14B	0.6552	0.5321	0.2813	0.055*
H14C	0.6896	0.4704	0.2010	0.055*
C15	1.04692 (10)	0.77094 (10)	0.38361 (10)	0.0162 (3)
C16	1.06181 (12)	0.72906 (13)	0.46947 (11)	0.0253 (4)
H16	1.1218	0.7118	0.4953	0.030*
C17	0.98915 (13)	0.71256 (14)	0.51739 (12)	0.0326 (4)
H17	0.9994	0.6828	0.5755	0.039*
C18	0.90163 (12)	0.73933 (13)	0.48099 (12)	0.0290 (4)
H18	0.8522	0.7297	0.5147	0.035*
C19	0.88646 (11)	0.78013 (12)	0.39528 (11)	0.0237 (4)
H19	0.8264	0.7980	0.3701	0.028*
C20	0.95841 (10)	0.79518 (11)	0.34577 (11)	0.0190 (3)
H20	0.9474	0.8218	0.2864	0.023*
C21	1.12797 (10)	0.79444 (10)	0.33795 (10)	0.0149 (3)
C22	1.18641 (10)	0.83429 (10)	0.19877 (9)	0.0143 (3)
C23	1.13244 (10)	1.00932 (11)	0.20189 (10)	0.0181 (3)
H23	1.1600	1.0720	0.1831	0.022*
C24	1.12179 (11)	1.02287 (11)	0.30114 (10)	0.0200 (3)
H24A	1.0985	1.0891	0.3105	0.030*
H24B	1.1811	1.0144	0.3382	0.030*
H24C	1.0789	0.9738	0.3187	0.030*
C25	1.04171 (11)	0.99951 (12)	0.14111 (11)	0.0256 (4)
H25A	1.0527	0.9926	0.0781	0.038*
H25B	1.0047	1.0584	0.1472	0.038*
H25C	1.0093	0.9413	0.1590	0.038*
C26	1.27615 (12)	0.96155 (12)	0.13727 (12)	0.0271 (4)
H26	1.3095	0.9008	0.1228	0.033*
C27	1.34174 (12)	1.02249 (13)	0.20183 (14)	0.0340 (4)
H27A	1.3604	0.9847	0.2571	0.051*
H27B	1.3116	1.0833	0.2170	0.051*
H27C	1.3956	1.0388	0.1730	0.051*
C28	1.24534 (15)	1.01339 (15)	0.04833 (13)	0.0446 (5)
H28A	1.2010	0.9721	0.0109	0.067*
H28B	1.2981	1.0251	0.0164	0.067*
H28C	1.2170	1.0764	0.0602	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.0237 (2)	0.01671 (18)	0.0177 (2)	0.00430 (15)	0.00614 (16)	−0.00098 (14)
S2	0.0191 (2)	0.01741 (18)	0.0205 (2)	0.00404 (14)	0.00623 (15)	0.00049 (14)
O1	0.0178 (6)	0.0305 (6)	0.0161 (5)	−0.0038 (5)	−0.0002 (4)	−0.0028 (5)
O2	0.0143 (6)	0.0287 (6)	0.0156 (5)	0.0002 (4)	−0.0011 (4)	0.0005 (4)
N1	0.0135 (6)	0.0170 (6)	0.0098 (6)	−0.0006 (5)	0.0010 (5)	0.0005 (5)
N2	0.0200 (7)	0.0146 (6)	0.0144 (6)	−0.0006 (5)	0.0058 (5)	−0.0014 (5)
N3	0.0116 (6)	0.0160 (6)	0.0129 (6)	−0.0011 (5)	0.0007 (5)	0.0003 (5)
N4	0.0200 (7)	0.0154 (6)	0.0175 (6)	−0.0005 (5)	0.0081 (5)	−0.0003 (5)
C1	0.0148 (7)	0.0134 (7)	0.0169 (7)	0.0013 (5)	0.0026 (6)	0.0016 (6)
C2	0.0161 (8)	0.0192 (7)	0.0214 (8)	0.0004 (6)	0.0005 (6)	0.0012 (6)
C3	0.0136 (8)	0.0216 (8)	0.0294 (9)	0.0005 (6)	0.0052 (7)	0.0034 (6)
C4	0.0214 (8)	0.0192 (8)	0.0217 (8)	0.0022 (6)	0.0096 (7)	0.0017 (6)
C5	0.0192 (8)	0.0185 (7)	0.0177 (8)	0.0023 (6)	0.0046 (6)	0.0014 (6)
C6	0.0142 (7)	0.0171 (7)	0.0181 (7)	0.0000 (6)	0.0032 (6)	0.0009 (6)
C7	0.0145 (7)	0.0143 (7)	0.0167 (7)	0.0009 (6)	0.0007 (6)	−0.0002 (6)
C8	0.0116 (7)	0.0181 (7)	0.0126 (7)	−0.0017 (6)	0.0005 (6)	−0.0009 (6)
C9	0.0260 (9)	0.0134 (7)	0.0176 (8)	0.0023 (6)	0.0050 (6)	−0.0008 (6)
C10	0.0286 (10)	0.0216 (8)	0.0323 (10)	0.0071 (7)	0.0090 (8)	0.0028 (7)
C11	0.0416 (11)	0.0195 (8)	0.0256 (9)	0.0008 (7)	−0.0015 (8)	−0.0059 (7)
C12	0.0394 (10)	0.0190 (8)	0.0206 (8)	−0.0025 (7)	0.0172 (7)	0.0002 (6)
C13	0.0594 (13)	0.0255 (9)	0.0180 (8)	−0.0026 (8)	0.0090 (8)	0.0029 (7)
C14	0.0405 (12)	0.0258 (9)	0.0486 (12)	−0.0037 (8)	0.0272 (10)	−0.0002 (8)
C15	0.0172 (8)	0.0164 (7)	0.0155 (7)	−0.0023 (6)	0.0038 (6)	−0.0011 (6)
C16	0.0226 (9)	0.0355 (9)	0.0178 (8)	−0.0006 (7)	0.0027 (7)	0.0034 (7)
C17	0.0370 (11)	0.0463 (11)	0.0158 (8)	−0.0056 (9)	0.0080 (8)	0.0066 (7)
C18	0.0263 (10)	0.0370 (10)	0.0267 (9)	−0.0069 (7)	0.0142 (8)	−0.0026 (7)
C19	0.0176 (8)	0.0266 (8)	0.0282 (9)	−0.0015 (6)	0.0072 (7)	−0.0013 (7)
C20	0.0181 (8)	0.0199 (7)	0.0193 (8)	−0.0015 (6)	0.0039 (6)	0.0010 (6)
C21	0.0163 (8)	0.0135 (7)	0.0149 (7)	0.0011 (6)	0.0015 (6)	0.0000 (5)
C22	0.0133 (7)	0.0182 (7)	0.0108 (7)	−0.0004 (6)	−0.0012 (6)	−0.0007 (5)
C23	0.0218 (8)	0.0140 (7)	0.0189 (8)	0.0022 (6)	0.0045 (6)	0.0010 (6)
C24	0.0249 (9)	0.0167 (7)	0.0193 (8)	0.0016 (6)	0.0067 (7)	−0.0012 (6)
C25	0.0290 (9)	0.0215 (8)	0.0247 (9)	0.0045 (7)	−0.0029 (7)	0.0012 (7)
C26	0.0307 (10)	0.0210 (8)	0.0345 (10)	−0.0038 (7)	0.0225 (8)	−0.0020 (7)
C27	0.0254 (10)	0.0310 (9)	0.0485 (12)	−0.0062 (8)	0.0153 (9)	0.0021 (8)
C28	0.0648 (15)	0.0468 (12)	0.0270 (10)	−0.0187 (10)	0.0240 (10)	0.0011 (9)

S1—C8	1.6687 (15)	C12—C13	1.525 (2)
S2—C22	1.6689 (15)	C12—H12	1.0000
O1—C7	1.2304 (18)	C13—H13A	0.9800
O2—C21	1.2343 (18)	C13—H13B	0.9800
N1—C7	1.3537 (19)	C13—H13C	0.9800
N1—C8	1.4362 (18)	C14—H14A	0.9800
N1—H1	0.847 (9)	C14—H14B	0.9800
N2—C8	1.3266 (18)	C14—H14C	0.9800
N2—C12	1.4877 (18)	C15—C16	1.392 (2)
N2—C9	1.4986 (18)	C15—C20	1.396 (2)
N3—C21	1.3542 (18)	C15—C21	1.491 (2)
N3—C22	1.4316 (18)	C16—C17	1.387 (2)
N3—H3	0.854 (9)	C16—H16	0.9500
N4—C22	1.3260 (18)	C17—C18	1.385 (3)
N4—C26	1.4915 (19)	C17—H17	0.9500
N4—C23	1.5035 (18)	C18—C19	1.384 (2)
C1—C6	1.397 (2)	C18—H18	0.9500
C1—C2	1.395 (2)	C19—C20	1.390 (2)
C1—C7	1.498 (2)	C19—H19	0.9500
C2—C3	1.386 (2)	C20—H20	0.9500
C2—H2	0.9500	C23—C24	1.521 (2)
C3—C4	1.384 (2)	C23—C25	1.523 (2)
C3—H3A	0.9500	C23—H23	1.0000
C4—C5	1.389 (2)	C24—H24A	0.9800
C4—H4	0.9500	C24—H24B	0.9800
C5—C6	1.389 (2)	C24—H24C	0.9800
C5—H5	0.9500	C25—H25A	0.9800
C6—H6	0.9500	C25—H25B	0.9800
C9—C10	1.520 (2)	C25—H25C	0.9800
C9—C11	1.523 (2)	C26—C27	1.519 (3)
C9—H9	1.0000	C26—C28	1.518 (3)
C10—H10A	0.9800	C26—H26	1.0000
C10—H10B	0.9800	C27—H27A	0.9800
C10—H10C	0.9800	C27—H27B	0.9800
C11—H11A	0.9800	C27—H27C	0.9800
C11—H11B	0.9800	C28—H28A	0.9800
C11—H11C	0.9800	C28—H28B	0.9800
C12—C14	1.517 (2)	C28—H28C	0.9800
C7—N1—C8	118.40 (12)	C12—C14—H14A	109.5
C7—N1—H1	121.3 (13)	C12—C14—H14B	109.5
C8—N1—H1	117.8 (13)	H14A—C14—H14B	109.5
C8—N2—C12	119.46 (12)	C12—C14—H14C	109.5
C8—N2—C9	125.33 (12)	H14A—C14—H14C	109.5
C12—N2—C9	115.11 (11)	H14B—C14—H14C	109.5
C21—N3—C22	120.13 (12)	C16—C15—C20	119.60 (14)
C21—N3—H3	121.7 (14)	C16—C15—C21	117.98 (14)
C22—N3—H3	114.7 (14)	C20—C15—C21	122.29 (13)
C22—N4—C26	119.31 (12)	C17—C16—C15	120.10 (16)
C22—N4—C23	124.95 (12)	C17—C16—H16	120.0
C26—N4—C23	115.61 (11)	C15—C16—H16	120.0
C6—C1—C2	119.44 (14)	C18—C17—C16	120.32 (16)
C6—C1—C7	123.75 (13)	C18—C17—H17	119.8
C2—C1—C7	116.70 (13)	C16—C17—H17	119.8
C3—C2—C1	120.20 (15)	C19—C18—C17	119.72 (15)
C3—C2—H2	119.9	C19—C18—H18	120.1
C1—C2—H2	119.9	C17—C18—H18	120.1
C4—C3—C2	120.46 (14)	C18—C19—C20	120.53 (16)
C4—C3—H3A	119.8	C18—C19—H19	119.7
C2—C3—H3A	119.8	C20—C19—H19	119.7
C3—C4—C5	119.49 (14)	C19—C20—C15	119.69 (15)
C3—C4—H4	120.3	C19—C20—H20	120.2
C5—C4—H4	120.3	C15—C20—H20	120.2
C6—C5—C4	120.67 (15)	O2—C21—N3	121.71 (13)
C6—C5—H5	119.7	O2—C21—C15	121.55 (13)
C4—C5—H5	119.7	N3—C21—C15	116.60 (13)
C5—C6—C1	119.72 (14)	N4—C22—N3	114.80 (12)
C5—C6—H6	120.1	N4—C22—S2	127.29 (11)
C1—C6—H6	120.1	N3—C22—S2	117.90 (10)
O1—C7—N1	120.86 (14)	N4—C23—C24	115.01 (12)
O1—C7—C1	121.15 (13)	N4—C23—C25	111.13 (12)
N1—C7—C1	117.83 (13)	C24—C23—C25	113.12 (13)
N2—C8—N1	114.50 (12)	N4—C23—H23	105.5
N2—C8—S1	127.50 (11)	C24—C23—H23	105.5
N1—C8—S1	118.00 (10)	C25—C23—H23	105.5
N2—C9—C10	113.40 (12)	C23—C24—H24A	109.5
N2—C9—C11	113.13 (13)	C23—C24—H24B	109.5
C10—C9—C11	113.26 (13)	H24A—C24—H24B	109.5
N2—C9—H9	105.3	C23—C24—H24C	109.5
C10—C9—H9	105.3	H24A—C24—H24C	109.5
C11—C9—H9	105.3	H24B—C24—H24C	109.5
C9—C10—H10A	109.5	C23—C25—H25A	109.5
C9—C10—H10B	109.5	C23—C25—H25B	109.5
H10A—C10—H10B	109.5	H25A—C25—H25B	109.5
C9—C10—H10C	109.5	C23—C25—H25C	109.5
H10A—C10—H10C	109.5	H25A—C25—H25C	109.5
H10B—C10—H10C	109.5	H25B—C25—H25C	109.5
C9—C11—H11A	109.5	N4—C26—C27	110.09 (13)
C9—C11—H11B	109.5	N4—C26—C28	111.89 (15)
H11A—C11—H11B	109.5	C27—C26—C28	113.20 (15)
C9—C11—H11C	109.5	N4—C26—H26	107.1
H11A—C11—H11C	109.5	C27—C26—H26	107.1
H11B—C11—H11C	109.5	C28—C26—H26	107.1
N2—C12—C14	110.44 (14)	C26—C27—H27A	109.5
N2—C12—C13	111.06 (13)	C26—C27—H27B	109.5
C14—C12—C13	113.39 (14)	H27A—C27—H27B	109.5
N2—C12—H12	107.2	C26—C27—H27C	109.5
C14—C12—H12	107.2	H27A—C27—H27C	109.5
C13—C12—H12	107.2	H27B—C27—H27C	109.5
C12—C13—H13A	109.5	C26—C28—H28A	109.5
C12—C13—H13B	109.5	C26—C28—H28B	109.5
H13A—C13—H13B	109.5	H28A—C28—H28B	109.5
C12—C13—H13C	109.5	C26—C28—H28C	109.5
H13A—C13—H13C	109.5	H28A—C28—H28C	109.5
H13B—C13—H13C	109.5	H28B—C28—H28C	109.5
C6—C1—C2—C3	−0.9 (2)	C20—C15—C16—C17	−0.7 (2)
C7—C1—C2—C3	175.51 (13)	C21—C15—C16—C17	175.26 (15)
C1—C2—C3—C4	−0.1 (2)	C15—C16—C17—C18	−1.3 (3)
C2—C3—C4—C5	1.0 (2)	C16—C17—C18—C19	1.9 (3)
C3—C4—C5—C6	−1.0 (2)	C17—C18—C19—C20	−0.5 (3)
C4—C5—C6—C1	0.0 (2)	C18—C19—C20—C15	−1.4 (2)
C2—C1—C6—C5	0.9 (2)	C16—C15—C20—C19	2.0 (2)
C7—C1—C6—C5	−175.24 (13)	C21—C15—C20—C19	−173.76 (14)
C8—N1—C7—O1	4.8 (2)	C22—N3—C21—O2	4.6 (2)
C8—N1—C7—C1	−179.69 (12)	C22—N3—C21—C15	−179.58 (12)
C6—C1—C7—O1	−179.23 (14)	C16—C15—C21—O2	−19.9 (2)
C2—C1—C7—O1	4.5 (2)	C20—C15—C21—O2	155.89 (14)
C6—C1—C7—N1	5.2 (2)	C16—C15—C21—N3	164.24 (14)
C2—C1—C7—N1	−171.00 (13)	C20—C15—C21—N3	−19.9 (2)
C12—N2—C8—N1	176.10 (13)	C26—N4—C22—N3	176.26 (13)
C9—N2—C8—N1	−7.7 (2)	C23—N4—C22—N3	−8.0 (2)
C12—N2—C8—S1	−3.9 (2)	C26—N4—C22—S2	−5.0 (2)
C9—N2—C8—S1	172.33 (11)	C23—N4—C22—S2	170.75 (11)
C7—N1—C8—N2	−96.09 (16)	C21—N3—C22—N4	−99.35 (15)
C7—N1—C8—S1	83.90 (15)	C21—N3—C22—S2	81.77 (15)
C8—N2—C9—C10	72.10 (19)	C22—N4—C23—C24	63.67 (19)
C12—N2—C9—C10	−111.54 (15)	C26—N4—C23—C24	−120.46 (15)
C8—N2—C9—C11	−58.6 (2)	C22—N4—C23—C25	−66.49 (18)
C12—N2—C9—C11	117.72 (15)	C26—N4—C23—C25	109.38 (15)
C8—N2—C12—C14	106.66 (16)	C22—N4—C26—C27	−113.95 (16)
C9—N2—C12—C14	−69.93 (17)	C23—N4—C26—C27	69.92 (18)
C8—N2—C12—C13	−126.65 (15)	C22—N4—C26—C28	119.25 (16)
C9—N2—C12—C13	56.76 (17)	C23—N4—C26—C28	−56.87 (18)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.85 (1)	2.03 (1)	2.8568 (16)	167 (2)
N3—H3···O1	0.85 (1)	1.94 (1)	2.7728 (16)	163 (2)
C6—H6···O2i	0.95	2.40	3.3306 (18)	166
C10—H10c···Cgii	0.98	2.63	3.5714 (18)	160
C25—H25b···Cgiii	0.98	2.70	3.5717 (18)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.85 (1)	2.03 (1)	2.8568 (16)	167 (2)
N3—H3⋯O1	0.85 (1)	1.94 (1)	2.7728 (16)	163 (2)
C6—H6⋯O2i	0.95	2.40	3.3306 (18)	166
C10—H10c⋯Cgii	0.98	2.63	3.5714 (18)	160
C25—H25b⋯Cgiii	0.98	2.70	3.5717 (18)	149

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