Ethyl 2-(3,3-dibutyl-thio-ureido)-4,5,6,7-tetra-hydro-benzo[b]thio-phene-3-carboxyl-ate.

In the title compound, C(20)H(32)N(2)O(2)S(2), the cyclo-hexene ring is disordered over two half-boat conformations with occupancy factors of 0.71:0.29. One n-butyl chain is also disordered over two positions with occupancy factors of 0.83:0.17. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond.

Related literature

For the synthesis and biological activity of thienopyrimidin-4(3H)-one derivatives, see: De Laszlo et al. (1992a ▶,b ▶); Taguchi et al. (1993a ▶,b ▶); Walter (1999a ▶,b ▶); Ding et al. (2004 ▶); Santagati et al. (2003 ▶); Abbott GmbH Co KG (2004a ▶, 2004b ▶); Walter & Zeun (2004 ▶); Ford et al. (2004a ▶,b ▶); Duval et al. (2005 ▶); Waehaelae et al. (2004a ▶,b ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For related structures, see: Xu et al. (2005 ▶); Zeng et al. (2005 ▶, 2006 ▶, 2007 ▶, 2008 ▶, 2009 ▶); Wang et al. (2007 ▶, 2008 ▶); Zheng et al. (2007 ▶); Xie et al. (2008 ▶).

Experimental

Crystal data

C20H32N2O2S2

M = 396.60

Monoclinic,

a = 10.9311 (11) Å

b = 21.715 (3) Å

c = 9.6841 (3) Å

β = 107.711 (12)°

V = 2189.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 292 K

0.36 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.903, T max = 0.938

12194 measured reflections

4036 independent reflections

3460 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.153

S = 1.21

4036 reflections

280 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.23 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, 2009 ▶); software used to prepare material for publication: SHELXTL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047230/rz2377sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047230/rz2377Isup2.hkl

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

C20H32N2O2S2	F(000) = 856
Mr = 396.60	Dx = 1.203 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9055 reflections
a = 10.9311 (11) Å	θ = 2.2–27.6°
b = 21.715 (3) Å	µ = 0.26 mm−1
c = 9.6841 (3) Å	T = 292 K
β = 107.711 (12)°	Block, colourless
V = 2189.8 (4) Å3	0.36 × 0.30 × 0.25 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4036 independent reflections
Radiation source: fine-focus sealed tube	3460 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.903, Tmax = 0.938	k = −21→26
12194 measured reflections	l = −11→11

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ2(Fo2) + (0.0275P)2 + 2.0031P] where P = (Fo2 + 2Fc2)/3
4036 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.30 e Å−3
13 restraints	Δρmin = −0.23 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)
C1	1.0984 (4)	−0.00230 (16)	0.7833 (4)	0.0631 (9)
C2	1.1175 (5)	−0.0488 (2)	0.9023 (5)	0.0856 (12)
H2A	1.0446	−0.0765	0.8804	0.103*	0.71
H2B	1.1237	−0.0280	0.9928	0.103*	0.71
H2C	1.0714	−0.0361	0.9687	0.103*	0.29
H2D	1.0832	−0.0882	0.8616	0.103*	0.29
C3	1.2396 (7)	−0.0852 (4)	0.9174 (11)	0.097 (2)	0.71
H3A	1.2660	−0.1048	1.0119	0.117*	0.71
H3B	1.2207	−0.1175	0.8448	0.117*	0.71
C4	1.3461 (8)	−0.0488 (4)	0.9018 (8)	0.093 (2)	0.71
H4A	1.4202	−0.0754	0.9147	0.112*	0.71
H4B	1.3686	−0.0177	0.9771	0.112*	0.71
C4'	1.315 (2)	−0.0763 (7)	0.8441 (17)	0.077 (5)	0.29
H4'1	1.4018	−0.0918	0.8832	0.092*	0.29
H4'2	1.2627	−0.1081	0.7835	0.092*	0.29
C3'	1.2569 (14)	−0.0586 (11)	0.9758 (17)	0.113 (9)	0.29
H3'1	1.2705	−0.0918	1.0458	0.135*	0.29
H3'2	1.2968	−0.0215	1.0251	0.135*	0.29
C5	1.3142 (4)	−0.01737 (18)	0.7532 (4)	0.0751 (10)
H5A	1.3787	0.0136	0.7554	0.090*	0.71
H5B	1.3163	−0.0476	0.6803	0.090*	0.71
H5C	1.3789	0.0116	0.8067	0.090*	0.29
H5D	1.3339	−0.0286	0.6653	0.090*	0.29
C6	1.1838 (3)	0.01239 (15)	0.7127 (3)	0.0577 (8)
C7	1.1347 (3)	0.05951 (15)	0.6064 (3)	0.0551 (8)
C8	1.0133 (3)	0.07897 (14)	0.6033 (3)	0.0542 (7)
C9	1.1975 (3)	0.08581 (17)	0.5067 (4)	0.0634 (9)
C10	1.3820 (4)	0.0835 (2)	0.4231 (5)	0.0951 (14)
H10A	1.3581	0.1259	0.3967	0.114*
H10B	1.4735	0.0824	0.4730	0.114*
C11	1.3540 (5)	0.0462 (2)	0.2931 (5)	0.1069 (16)
H11A	1.3741	0.0040	0.3193	0.160*
H11B	1.4048	0.0602	0.2340	0.160*
H11C	1.2646	0.0498	0.2398	0.160*
C12	0.8369 (3)	0.15459 (17)	0.5066 (4)	0.0659 (9)
C13	0.6951 (5)	0.2433 (2)	0.4072 (6)	0.1029 (15)
H13A	0.6756	0.2414	0.4983	0.123*
H13B	0.7147	0.2858	0.3911	0.123*
C14	0.5827 (5)	0.2238 (3)	0.2904 (6)	0.1242 (19)
H14A	0.5686	0.1800	0.2980	0.149*	0.83
H14B	0.5957	0.2317	0.1973	0.149*	0.83
H14C	0.5373	0.1905	0.3203	0.149*	0.17
H14D	0.6066	0.2106	0.2064	0.149*	0.17
C15	0.4615 (9)	0.2616 (5)	0.3037 (12)	0.181 (5)	0.83
H15A	0.3847	0.2396	0.2496	0.217*	0.83
H15B	0.4641	0.2612	0.4047	0.217*	0.83
C16	0.4496 (12)	0.3174 (5)	0.2607 (16)	0.232 (7)	0.83
H16A	0.5305	0.3381	0.2977	0.348*	0.83
H16B	0.3864	0.3376	0.2953	0.348*	0.83
H16C	0.4228	0.3184	0.1567	0.348*	0.83
C15'	0.4923 (18)	0.2749 (12)	0.213 (3)	0.090 (8)	0.17
H15C	0.5365	0.3140	0.2372	0.108*	0.17
H15D	0.4727	0.2690	0.1094	0.108*	0.17
C16'	0.372 (2)	0.2782 (14)	0.248 (5)	0.125 (13)	0.17
H16D	0.3180	0.3090	0.1892	0.188*	0.17
H16E	0.3897	0.2888	0.3487	0.188*	0.17
H16F	0.3298	0.2390	0.2303	0.188*	0.17
C17	0.9008 (4)	0.23002 (19)	0.3483 (5)	0.0814 (11)
H17A	0.8536	0.2535	0.2637	0.098*
H17B	0.9449	0.1968	0.3162	0.098*
C18	0.9998 (4)	0.2719 (2)	0.4523 (5)	0.0897 (13)
H18A	0.9553	0.3058	0.4813	0.108*
H18B	1.0437	0.2487	0.5388	0.108*
C19	1.0961 (5)	0.2970 (2)	0.3882 (5)	0.1017 (15)
H19A	1.0523	0.3158	0.2955	0.122*
H19B	1.1485	0.2635	0.3709	0.122*
C20	1.1828 (5)	0.3447 (2)	0.4862 (6)	0.126 (2)
H20A	1.1321	0.3792	0.4981	0.190*
H20B	1.2465	0.3582	0.4432	0.190*
H20C	1.2244	0.3266	0.5791	0.190*
N1	0.9493 (3)	0.12572 (14)	0.5138 (3)	0.0637 (7)
H1A	0.997 (3)	0.1387 (16)	0.464 (3)	0.076*
N2	0.8108 (3)	0.20414 (16)	0.4177 (4)	0.0801 (9)
O1	1.3122 (2)	0.06116 (13)	0.5196 (3)	0.0769 (7)
O2	1.1519 (3)	0.12628 (13)	0.4189 (3)	0.0869 (8)
S1	0.95706 (9)	0.03954 (4)	0.72506 (10)	0.0662 (3)
S2	0.74212 (10)	0.13005 (5)	0.60210 (13)	0.0823 (3)

	U11	U22	U33	U12	U13	U23
C1	0.080 (2)	0.060 (2)	0.0549 (19)	−0.0045 (17)	0.0284 (17)	−0.0010 (16)
C2	0.106 (3)	0.085 (3)	0.075 (3)	0.006 (2)	0.041 (2)	0.018 (2)
C3	0.109 (6)	0.097 (6)	0.093 (6)	0.026 (4)	0.040 (5)	0.035 (5)
C4	0.094 (5)	0.099 (6)	0.083 (6)	0.014 (5)	0.021 (5)	0.019 (4)
C4'	0.083 (12)	0.078 (11)	0.068 (10)	0.020 (9)	0.021 (9)	−0.004 (8)
C3'	0.18 (2)	0.106 (17)	0.053 (10)	0.055 (16)	0.040 (12)	0.009 (9)
C5	0.079 (2)	0.074 (2)	0.077 (3)	0.010 (2)	0.030 (2)	0.006 (2)
C6	0.0649 (19)	0.0570 (19)	0.0541 (18)	−0.0018 (16)	0.0225 (15)	−0.0035 (15)
C7	0.0634 (19)	0.0523 (17)	0.0542 (18)	−0.0054 (15)	0.0248 (15)	−0.0023 (14)
C8	0.0610 (18)	0.0520 (18)	0.0511 (17)	−0.0049 (15)	0.0194 (15)	−0.0051 (14)
C9	0.068 (2)	0.062 (2)	0.067 (2)	−0.0079 (17)	0.0303 (18)	0.0015 (18)
C10	0.081 (3)	0.113 (4)	0.108 (4)	−0.012 (3)	0.053 (3)	0.013 (3)
C11	0.111 (4)	0.130 (4)	0.102 (4)	−0.005 (3)	0.065 (3)	0.004 (3)
C12	0.062 (2)	0.065 (2)	0.068 (2)	0.0013 (17)	0.0149 (17)	−0.0078 (18)
C13	0.098 (3)	0.094 (3)	0.116 (4)	0.013 (3)	0.031 (3)	0.008 (3)
C14	0.090 (4)	0.154 (5)	0.118 (4)	0.010 (4)	0.015 (3)	0.014 (4)
C15	0.111 (7)	0.256 (15)	0.161 (9)	0.068 (8)	0.021 (6)	0.083 (9)
C16	0.180 (11)	0.235 (14)	0.296 (17)	0.081 (11)	0.096 (11)	0.137 (14)
C15'	0.09 (2)	0.087 (19)	0.09 (2)	0.015 (16)	0.029 (17)	0.017 (16)
C16'	0.10 (3)	0.10 (2)	0.18 (4)	−0.02 (2)	0.05 (3)	0.03 (2)
C17	0.084 (3)	0.076 (3)	0.079 (3)	0.008 (2)	0.017 (2)	0.016 (2)
C18	0.092 (3)	0.086 (3)	0.087 (3)	−0.001 (2)	0.020 (2)	0.009 (2)
C19	0.109 (4)	0.089 (3)	0.104 (4)	−0.005 (3)	0.027 (3)	0.015 (3)
C20	0.119 (4)	0.102 (4)	0.137 (5)	−0.025 (3)	0.007 (4)	0.003 (4)
N1	0.0641 (17)	0.0633 (18)	0.0680 (19)	0.0034 (14)	0.0262 (14)	0.0037 (15)
N2	0.073 (2)	0.076 (2)	0.090 (2)	0.0137 (17)	0.0216 (18)	0.0066 (19)
O1	0.0683 (15)	0.0907 (19)	0.0836 (18)	−0.0001 (14)	0.0410 (14)	0.0126 (14)
O2	0.094 (2)	0.0862 (19)	0.095 (2)	0.0115 (16)	0.0501 (17)	0.0313 (16)
S1	0.0714 (6)	0.0700 (6)	0.0664 (6)	−0.0047 (4)	0.0345 (4)	0.0008 (4)
S2	0.0682 (6)	0.0924 (8)	0.0923 (8)	−0.0011 (5)	0.0333 (5)	−0.0054 (6)

C1—C6	1.352 (4)	C12—N2	1.353 (5)
C1—C2	1.498 (5)	C12—N1	1.362 (4)
C1—S1	1.732 (4)	C12—S2	1.672 (4)
C2—C3'	1.488 (15)	C13—C14	1.457 (6)
C2—C3	1.520 (8)	C13—N2	1.502 (5)
C2—H2A	0.9700	C13—H13A	0.9700
C2—H2B	0.9700	C13—H13B	0.9700
C2—H2C	0.9700	C14—C15'	1.522 (16)
C2—H2D	0.9700	C14—C15	1.597 (9)
C3—C4	1.452 (11)	C14—H14A	0.9700
C3—H3A	0.9700	C14—H14B	0.9700
C3—H3B	0.9700	C14—H14C	0.9700
C4—C5	1.534 (7)	C14—H14D	0.9700
C4—H4A	0.9700	C15—C16	1.274 (11)
C4—H4B	0.9700	C15—H15A	0.9700
C4'—C5	1.552 (14)	C15—H15B	0.9700
C4'—C3'	1.63 (2)	C16—H16A	0.9600
C4'—H4'1	0.9700	C16—H16B	0.9600
C4'—H4'2	0.9700	C16—H16C	0.9600
C3'—H3'1	0.9700	C15'—C16'	1.454 (19)
C3'—H3'2	0.9700	C15'—H15C	0.9700
C5—C6	1.505 (5)	C15'—H15D	0.9700
C5—H5A	0.9700	C16'—H16D	0.9600
C5—H5B	0.9700	C16'—H16E	0.9600
C5—H5C	0.9700	C16'—H16F	0.9600
C5—H5D	0.9700	C17—N2	1.461 (5)
C6—C7	1.435 (4)	C17—C18	1.532 (6)
C7—C8	1.385 (4)	C17—H17A	0.9700
C7—C9	1.460 (4)	C17—H17B	0.9700
C8—N1	1.380 (4)	C18—C19	1.480 (6)
C8—S1	1.715 (3)	C18—H18A	0.9700
C9—O2	1.219 (4)	C18—H18B	0.9700
C9—O1	1.333 (4)	C19—C20	1.524 (6)
C10—C11	1.449 (6)	C19—H19A	0.9700
C10—O1	1.458 (4)	C19—H19B	0.9700
C10—H10A	0.9700	C20—H20A	0.9600
C10—H10B	0.9700	C20—H20B	0.9600
C11—H11A	0.9600	C20—H20C	0.9600
C11—H11B	0.9600	N1—H1A	0.86 (3)
C11—H11C	0.9600
C6—C1—C2	126.3 (4)	C10—C11—H11B	109.5
C6—C1—S1	113.3 (3)	H11A—C11—H11B	109.5
C2—C1—S1	120.4 (3)	C10—C11—H11C	109.5
C3'—C2—C1	110.3 (8)	H11A—C11—H11C	109.5
C1—C2—C3	109.7 (4)	H11B—C11—H11C	109.5
C3'—C2—H2A	132.0	N2—C12—N1	114.3 (3)
C1—C2—H2A	109.7	N2—C12—S2	124.0 (3)
C3—C2—H2A	109.7	N1—C12—S2	121.7 (3)
C3'—C2—H2B	81.6	C14—C13—N2	112.5 (4)
C1—C2—H2B	109.7	C14—C13—H13A	109.1
C3—C2—H2B	109.7	N2—C13—H13A	109.1
H2A—C2—H2B	108.2	C14—C13—H13B	109.1
C3'—C2—H2C	112.7	N2—C13—H13B	109.1
C1—C2—H2C	109.8	H13A—C13—H13B	107.8
C3—C2—H2C	134.6	C13—C14—C15'	116.0 (11)
H2A—C2—H2C	76.3	C13—C14—C15	108.2 (6)
C3'—C2—H2D	106.3	C13—C14—H14A	110.1
C1—C2—H2D	109.6	C15'—C14—H14A	131.1
C3—C2—H2D	78.4	C15—C14—H14A	110.1
H2B—C2—H2D	133.7	C13—C14—H14B	110.1
H2C—C2—H2D	107.8	C15—C14—H14B	110.1
C4—C3—C2	114.6 (6)	H14A—C14—H14B	108.4
C4—C3—H3A	108.6	C13—C14—H14C	111.9
C2—C3—H3A	108.6	C15'—C14—H14C	112.0
C4—C3—H3B	108.6	H14B—C14—H14C	130.0
C2—C3—H3B	108.6	C13—C14—H14D	111.0
H3A—C3—H3B	107.6	C15'—C14—H14D	95.9
C3—C4—C5	112.3 (7)	C15—C14—H14D	131.3
C3—C4—H4A	109.2	H14C—C14—H14D	108.9
C5—C4—H4A	109.2	C16—C15—C14	117.9 (11)
C3—C4—H4B	109.2	C16—C15—H15A	107.8
C5—C4—H4B	109.2	C14—C15—H15A	107.8
H4A—C4—H4B	107.9	C16—C15—H15B	107.8
C5—C4'—C3'	108.2 (12)	C14—C15—H15B	107.8
C5—C4'—H4'1	110.1	H15A—C15—H15B	107.2
C3'—C4'—H4'1	110.1	C16'—C15'—C14	114.7 (19)
C5—C4'—H4'2	110.1	C16'—C15'—H15C	108.6
C3'—C4'—H4'2	110.1	C14—C15'—H15C	108.6
H4'1—C4'—H4'2	108.4	C16'—C15'—H15D	108.6
C2—C3'—C4'	104.1 (12)	C14—C15'—H15D	108.6
C2—C3'—H3'1	110.9	H15C—C15'—H15D	107.6
C4'—C3'—H3'1	110.9	C15'—C16'—H16D	109.5
C2—C3'—H3'2	110.9	C15'—C16'—H16E	109.5
C4'—C3'—H3'2	110.9	H16D—C16'—H16E	109.5
H3'1—C3'—H3'2	109.0	C15'—C16'—H16F	109.5
C6—C5—C4	111.3 (4)	H16D—C16'—H16F	109.5
C6—C5—C4'	110.0 (8)	H16E—C16'—H16F	109.5
C6—C5—H5A	109.4	N2—C17—C18	111.4 (4)
C4—C5—H5A	109.4	N2—C17—H17A	109.3
C4'—C5—H5A	133.0	C18—C17—H17A	109.3
C6—C5—H5B	109.4	N2—C17—H17B	109.3
C4—C5—H5B	109.4	C18—C17—H17B	109.3
H5A—C5—H5B	108.0	H17A—C17—H17B	108.0
C6—C5—H5C	109.9	C19—C18—C17	113.1 (4)
C4'—C5—H5C	110.8	C19—C18—H18A	108.9
H5B—C5—H5C	130.8	C17—C18—H18A	108.9
C6—C5—H5D	108.9	C19—C18—H18B	108.9
C4—C5—H5D	131.5	C17—C18—H18B	109.0
C4'—C5—H5D	109.0	H18A—C18—H18B	107.8
H5C—C5—H5D	108.1	C18—C19—C20	112.1 (4)
C1—C6—C7	111.5 (3)	C18—C19—H19A	109.2
C1—C6—C5	120.8 (3)	C20—C19—H19A	109.2
C7—C6—C5	127.6 (3)	C18—C19—H19B	109.2
C8—C7—C6	112.3 (3)	C20—C19—H19B	109.2
C8—C7—C9	120.4 (3)	H19A—C19—H19B	107.9
C6—C7—C9	127.2 (3)	C19—C20—H20A	109.5
N1—C8—C7	122.5 (3)	C19—C20—H20B	109.5
N1—C8—S1	125.5 (2)	H20A—C20—H20B	109.5
C7—C8—S1	112.0 (2)	C19—C20—H20C	109.5
O2—C9—O1	121.9 (3)	H20A—C20—H20C	109.5
O2—C9—C7	124.6 (3)	H20B—C20—H20C	109.5
O1—C9—C7	113.5 (3)	C12—N1—C8	130.4 (3)
C11—C10—O1	111.0 (4)	C12—N1—H1A	121 (3)
C11—C10—H10A	109.4	C8—N1—H1A	109 (3)
O1—C10—H10A	109.4	C12—N2—C17	123.9 (3)
C11—C10—H10B	109.4	C12—N2—C13	120.2 (4)
O1—C10—H10B	109.4	C17—N2—C13	114.9 (3)
H10A—C10—H10B	108.0	C9—O1—C10	117.8 (3)
C10—C11—H11A	109.5	C8—S1—C1	90.86 (16)
C6—C1—C2—C3'	23.4 (10)	C6—C7—C9—O2	−179.4 (4)
S1—C1—C2—C3'	−155.7 (8)	C8—C7—C9—O1	−178.1 (3)
C6—C1—C2—C3	−9.1 (7)	C6—C7—C9—O1	0.8 (5)
S1—C1—C2—C3	171.9 (5)	N2—C13—C14—C15'	−145.7 (11)
C3'—C2—C3—C4	−57.1 (15)	N2—C13—C14—C15	171.8 (5)
C1—C2—C3—C4	39.8 (10)	C13—C14—C15—C16	76.9 (14)
C2—C3—C4—C5	−59.9 (11)	C15'—C14—C15—C16	−32.1 (19)
C1—C2—C3'—C4'	−54.3 (15)	C13—C14—C15'—C16'	−106 (3)
C3—C2—C3'—C4'	40.2 (10)	C15—C14—C15'—C16'	−19 (2)
C5—C4'—C3'—C2	71.5 (17)	N2—C17—C18—C19	177.6 (4)
C3—C4—C5—C6	45.6 (9)	C17—C18—C19—C20	172.7 (4)
C3—C4—C5—C4'	−48.1 (16)	N2—C12—N1—C8	171.8 (3)
C3'—C4'—C5—C6	−50.6 (14)	S2—C12—N1—C8	−7.6 (5)
C3'—C4'—C5—C4	47.6 (13)	C7—C8—N1—C12	−172.7 (3)
C2—C1—C6—C7	−179.1 (4)	S1—C8—N1—C12	5.7 (5)
S1—C1—C6—C7	0.0 (4)	N1—C12—N2—C17	−7.3 (5)
C2—C1—C6—C5	−1.7 (6)	S2—C12—N2—C17	172.2 (3)
S1—C1—C6—C5	177.4 (3)	N1—C12—N2—C13	−175.5 (3)
C4—C5—C6—C1	−15.9 (6)	S2—C12—N2—C13	3.9 (5)
C4'—C5—C6—C1	17.0 (8)	C18—C17—N2—C12	−81.1 (5)
C4—C5—C6—C7	161.0 (5)	C18—C17—N2—C13	87.7 (4)
C4'—C5—C6—C7	−166.1 (7)	C14—C13—N2—C12	−92.5 (5)
C1—C6—C7—C8	0.8 (4)	C14—C13—N2—C17	98.3 (5)
C5—C6—C7—C8	−176.3 (3)	O2—C9—O1—C10	−0.9 (6)
C1—C6—C7—C9	−178.1 (3)	C7—C9—O1—C10	178.9 (3)
C5—C6—C7—C9	4.8 (6)	C11—C10—O1—C9	−92.2 (5)
C6—C7—C8—N1	177.3 (3)	N1—C8—S1—C1	−177.4 (3)
C9—C7—C8—N1	−3.7 (5)	C7—C8—S1—C1	1.1 (3)
C6—C7—C8—S1	−1.3 (4)	C6—C1—S1—C8	−0.7 (3)
C9—C7—C8—S1	177.7 (3)	C2—C1—S1—C8	178.5 (3)
C8—C7—C9—O2	1.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86 (3)	1.89 (2)	2.643 (4)	145 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86 (3)	1.89 (2)	2.643 (4)	145 (3)