[(Pyrrolidin-1-yl)carbothio-ylsulfan-yl]methyl pyrrolidine-1-carbodithio-ate.

The title compound, C(11)H(18)N(2)S(4), was unexpectedly obtained during studies on the reactivity of the complex tris-(acac-κ(2)O,O')gallium(III) (acac is acetyl-acetonate) with C(4)H(8)NCS(2)H in dichloro-methane. The title compound shows disordered two pyrrolidine rings with major and minor occupancies of 0.546 (4) and 0.454 (4). Two (pyrrolidin-1-yl)carbothio-ylsulfanyl units are linked together through a methyl-ene C atom and weak C-H⋯S inter-actions are found.

Related literature

For bis­(dialkyl­dithio­carbamates), CH2(S2CNR 2)2, see: R = Me (Thomas, 1945 ▶, 1946 ▶); R = Et (Heckley et al., 1970 ▶); R = C5H10 (Sharma et al., 1991 ▶). For weak C—H⋯S inter­actions, see: Kayed et al. (2008 ▶); Pervez et al. (2010 ▶); Vangala et al. (2002 ▶); Yaqub et al. (2010 ▶). For our previous work on the preparation of In(III) complexes, see: Chou et al. (2007 ▶). For C=S double-bond lengths, see: Pauling (1960 ▶).

Experimental

Crystal data

C11H18N2S4

M = 306.51

Orthorhombic,

a = 21.9118 (18) Å

b = 4.5705 (4) Å

c = 14.3452 (12) Å

V = 1436.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.64 mm−1

T = 150 K

0.25 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.856, T max = 0.910

17016 measured reflections

3292 independent reflections

2759 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.166

S = 1.07

3292 reflections

180 parameters

17 restraints

H-atom parameters constrained

Δρmax = 1.05 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1579 Friedel pairs

Flack parameter: −0.1 (2)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046027/bv2162sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046027/bv2162Isup2.hkl

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

C11H18N2S4	F(000) = 648
Mr = 306.51	Dx = 1.417 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2540 reflections
a = 21.9118 (18) Å	θ = 2.3–26.6°
b = 4.5705 (4) Å	µ = 0.64 mm−1
c = 14.3452 (12) Å	T = 150 K
V = 1436.6 (2) Å3	Block, light-brown
Z = 4	0.25 × 0.25 × 0.15 mm

Bruker SMART APEX CCD area-detector diffractometer	3292 independent reflections
Radiation source: fine-focus sealed tube	2759 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −28→28
Tmin = 0.856, Tmax = 0.910	k = −5→5
17016 measured reflections	l = −18→18

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)] = 0.062	H-atom parameters constrained
wR(F2) = 0.166	w = 1/[σ2(Fo2) + (0.1007P)2 + 0.6346P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.003
3292 reflections	Δρmax = 1.05 e Å−3
180 parameters	Δρmin = −0.27 e Å−3
17 restraints	Absolute structure: Flack (1983), 1579 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.1 (2)

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	0.34241 (4)	0.48896 (18)	0.20742 (6)	0.0247 (3)
S2	0.24742 (5)	0.4861 (2)	0.05150 (8)	0.0332 (3)
S3	0.40977 (4)	0.48200 (19)	0.02225 (7)	0.0292 (3)
S4	0.50250 (6)	0.4996 (2)	0.18040 (8)	0.0333 (3)
N1	0.23596 (13)	0.7324 (7)	0.2179 (2)	0.0280 (7)
N2	0.51532 (12)	0.7401 (7)	0.0131 (2)	0.0292 (7)
C1	0.2724 (4)	0.593 (2)	0.1603 (7)	0.0232 (12)	0.546 (4)
C2	0.1742 (5)	0.840 (3)	0.1934 (7)	0.0354 (9)	0.546 (4)
H2A	0.1450	0.6753	0.1894	0.043*	0.546 (4)
H2B	0.1749	0.9430	0.1327	0.043*	0.546 (4)
C3	0.1558 (4)	1.0519 (19)	0.2724 (6)	0.0388 (19)	0.546 (4)
H3A	0.1691	1.2541	0.2580	0.047*	0.546 (4)
H3B	0.1111	1.0507	0.2820	0.047*	0.546 (4)
C4	0.1889 (4)	0.935 (2)	0.3579 (6)	0.039 (2)	0.546 (4)
H4A	0.1669	0.7670	0.3857	0.047*	0.546 (4)
H4B	0.1943	1.0887	0.4057	0.047*	0.546 (4)
C5	0.2514 (4)	0.838 (2)	0.3155 (7)	0.0288 (11)	0.546 (4)
H5A	0.2803	1.0043	0.3132	0.035*	0.546 (4)
H5B	0.2698	0.6784	0.3528	0.035*	0.546 (4)
C1'	0.2682 (6)	0.549 (3)	0.1543 (10)	0.0232 (12)	0.454 (4)
C2'	0.1763 (6)	0.843 (4)	0.1926 (8)	0.0354 (9)	0.454 (4)
H2'A	0.1520	0.6948	0.1589	0.043*	0.454 (4)
H2'B	0.1794	1.0226	0.1541	0.043*	0.454 (4)
C3'	0.1491 (4)	0.910 (2)	0.2897 (7)	0.0388 (19)	0.454 (4)
H3'A	0.1174	1.0640	0.2862	0.047*	0.454 (4)
H3'B	0.1314	0.7321	0.3184	0.047*	0.454 (4)
C4'	0.2053 (4)	1.016 (2)	0.3437 (9)	0.039 (2)	0.454 (4)
H4'A	0.1985	1.0058	0.4119	0.047*	0.454 (4)
H4'B	0.2164	1.2183	0.3262	0.047*	0.454 (4)
C5'	0.2549 (5)	0.793 (3)	0.3119 (10)	0.0288 (11)	0.454 (4)
H5'A	0.2962	0.8811	0.3136	0.035*	0.454 (4)
H5'B	0.2544	0.6145	0.3508	0.035*	0.454 (4)
C6	0.4816 (3)	0.6102 (15)	0.0724 (6)	0.0200 (9)*	0.546 (4)
C7	0.5772 (5)	0.855 (3)	0.0389 (7)	0.0366 (10)	0.546 (4)
H7A	0.6075	0.6954	0.0428	0.044*	0.546 (4)
H7B	0.5760	0.9611	0.0990	0.044*	0.546 (4)
C8	0.5912 (4)	1.0600 (16)	−0.0409 (6)	0.033 (2)	0.546 (4)
H8A	0.5747	1.2579	−0.0287	0.040*	0.546 (4)
H8B	0.6358	1.0747	−0.0513	0.040*	0.546 (4)
C9	0.5603 (4)	0.9224 (18)	−0.1231 (5)	0.0301 (17)	0.546 (4)
H9A	0.5837	0.7523	−0.1464	0.036*	0.546 (4)
H9B	0.5551	1.0652	−0.1743	0.036*	0.546 (4)
C10	0.4984 (4)	0.827 (3)	−0.0837 (8)	0.0322 (10)	0.546 (4)
H10A	0.4687	0.9902	−0.0839	0.039*	0.546 (4)
H10B	0.4813	0.6600	−0.1191	0.039*	0.546 (4)
C6'	0.4807 (5)	0.551 (2)	0.0695 (8)	0.0200 (9)*	0.454 (4)
C7'	0.5740 (6)	0.853 (4)	0.0417 (8)	0.0366 (10)	0.454 (4)
H7'A	0.5983	0.7013	0.0740	0.044*	0.454 (4)
H7'B	0.5693	1.0245	0.0832	0.044*	0.454 (4)
C8'	0.6031 (4)	0.939 (2)	−0.0505 (8)	0.033 (2)	0.454 (4)
H8'A	0.6318	1.1039	−0.0417	0.040*	0.454 (4)
H8'B	0.6256	0.7717	−0.0778	0.040*	0.454 (4)
C9'	0.5511 (5)	1.027 (2)	−0.1120 (8)	0.0301 (17)	0.454 (4)
H9'A	0.5618	1.0074	−0.1788	0.036*	0.454 (4)
H9'B	0.5383	1.2315	−0.0996	0.036*	0.454 (4)
C10'	0.5010 (5)	0.808 (4)	−0.0837 (10)	0.0322 (10)	0.454 (4)
H10C	0.4599	0.8968	−0.0892	0.039*	0.454 (4)
H10D	0.5027	0.6299	−0.1230	0.039*	0.454 (4)
C11	0.37625 (18)	0.2698 (7)	0.1150 (4)	0.0358 (8)
H11A	0.4081	0.1426	0.1423	0.043*
H11B	0.3444	0.1413	0.0882	0.043*

	U11	U22	U33	U12	U13	U23
S1	0.0171 (4)	0.0341 (5)	0.0230 (6)	0.0012 (3)	−0.0019 (4)	0.0022 (3)
S2	0.0255 (5)	0.0514 (7)	0.0228 (6)	−0.0023 (4)	0.0000 (4)	−0.0059 (4)
S3	0.0214 (5)	0.0404 (6)	0.0259 (7)	−0.0009 (3)	0.0048 (4)	−0.0009 (4)
S4	0.0291 (5)	0.0535 (8)	0.0174 (6)	0.0030 (4)	0.0006 (4)	0.0072 (4)
N1	0.0272 (14)	0.0342 (15)	0.0226 (15)	0.0002 (12)	0.0001 (12)	0.0005 (12)
N2	0.0245 (13)	0.0388 (17)	0.0244 (15)	0.0028 (12)	0.0007 (12)	0.0005 (13)
C1	0.0175 (18)	0.031 (3)	0.0217 (19)	−0.0108 (19)	0.0036 (15)	0.003 (2)
C2	0.0293 (18)	0.049 (2)	0.0284 (18)	0.0045 (17)	−0.0025 (15)	−0.0022 (18)
C3	0.044 (3)	0.042 (5)	0.030 (4)	0.011 (3)	0.016 (3)	0.014 (3)
C4	0.026 (4)	0.059 (5)	0.033 (4)	−0.008 (3)	0.008 (3)	−0.002 (3)
C5	0.0359 (19)	0.025 (3)	0.0251 (18)	0.0014 (19)	−0.0016 (16)	−0.007 (2)
C1'	0.0175 (18)	0.031 (3)	0.0217 (19)	−0.0108 (19)	0.0036 (15)	0.003 (2)
C2'	0.0293 (18)	0.049 (2)	0.0284 (18)	0.0045 (17)	−0.0025 (15)	−0.0022 (18)
C3'	0.044 (3)	0.042 (5)	0.030 (4)	0.011 (3)	0.016 (3)	0.014 (3)
C4'	0.026 (4)	0.059 (5)	0.033 (4)	−0.008 (3)	0.008 (3)	−0.002 (3)
C5'	0.0359 (19)	0.025 (3)	0.0251 (18)	0.0014 (19)	−0.0016 (16)	−0.007 (2)
C7	0.0239 (18)	0.053 (3)	0.033 (2)	−0.0054 (17)	−0.0006 (16)	0.0003 (19)
C8	0.028 (3)	0.020 (5)	0.052 (5)	0.003 (3)	−0.010 (3)	0.009 (3)
C9	0.039 (3)	0.030 (5)	0.021 (3)	0.005 (3)	0.013 (3)	0.000 (3)
C10	0.037 (2)	0.036 (2)	0.0245 (19)	0.0014 (17)	−0.0037 (15)	−0.0016 (17)
C7'	0.0239 (18)	0.053 (3)	0.033 (2)	−0.0054 (17)	−0.0006 (16)	0.0003 (19)
C8'	0.028 (3)	0.020 (5)	0.052 (5)	0.003 (3)	−0.010 (3)	0.009 (3)
C9'	0.039 (3)	0.030 (5)	0.021 (3)	0.005 (3)	0.013 (3)	0.000 (3)
C10'	0.037 (2)	0.036 (2)	0.0245 (19)	0.0014 (17)	−0.0037 (15)	−0.0016 (17)
C11	0.0294 (15)	0.0314 (17)	0.047 (2)	−0.0009 (17)	0.0098 (14)	0.003 (2)

S1—C1	1.743 (10)	C2'—H2'A	0.9900
S1—C1'	1.816 (14)	C2'—H2'B	0.9900
S1—C11	1.820 (5)	C3'—C4'	1.533 (12)
S2—C1'	1.571 (14)	C3'—H3'A	0.9900
S2—C1	1.725 (10)	C3'—H3'B	0.9900
S3—C6'	1.724 (11)	C4'—C5'	1.556 (12)
S3—C11	1.802 (5)	C4'—H4'A	0.9900
S3—C6	1.827 (8)	C4'—H4'B	0.9900
S4—C6'	1.678 (12)	C5'—H5'A	0.9900
S4—C6	1.693 (8)	C5'—H5'B	0.9900
N1—C1	1.313 (10)	C7—C8	1.511 (11)
N1—C1'	1.426 (13)	C7—H7A	0.9900
N1—C5'	1.438 (13)	C7—H7B	0.9900
N1—C2'	1.448 (14)	C8—C9	1.498 (10)
N1—C2	1.483 (11)	C8—H8A	0.9900
N1—C5	1.520 (10)	C8—H8B	0.9900
N2—C6	1.273 (8)	C9—C10	1.531 (10)
N2—C6'	1.406 (11)	C9—H9A	0.9900
N2—C7'	1.445 (13)	C9—H9B	0.9900
N2—C10'	1.457 (14)	C10—H10A	0.9900
N2—C10	1.491 (11)	C10—H10B	0.9900
N2—C7	1.500 (11)	C7'—C8'	1.520 (12)
C2—C3	1.543 (11)	C7'—H7'A	0.9900
C2—H2A	0.9900	C7'—H7'B	0.9900
C2—H2B	0.9900	C8'—C9'	1.498 (11)
C3—C4	1.522 (10)	C8'—H8'A	0.9900
C3—H3A	0.9900	C8'—H8'B	0.9900
C3—H3B	0.9900	C9'—C10'	1.541 (12)
C4—C5	1.563 (10)	C9'—H9'A	0.9900
C4—H4A	0.9900	C9'—H9'B	0.9900
C4—H4B	0.9900	C10'—H10C	0.9900
C5—H5A	0.9900	C10'—H10D	0.9900
C5—H5B	0.9900	C11—H11A	0.9900
C2'—C3'	1.546 (12)	C11—H11B	0.9900
C1—S1—C1'	7.3 (7)	C2'—C3'—H3'A	111.4
C1—S1—C11	103.1 (4)	C4'—C3'—H3'B	111.4
C1'—S1—C11	98.2 (5)	C2'—C3'—H3'B	111.4
C1'—S2—C1	6.3 (9)	H3'A—C3'—H3'B	109.2
C6'—S3—C11	100.1 (4)	C3'—C4'—C5'	101.9 (9)
C6'—S3—C6	8.2 (4)	C3'—C4'—H4'A	111.4
C11—S3—C6	103.5 (3)	C5'—C4'—H4'A	111.4
C6'—S4—C6	9.3 (5)	C3'—C4'—H4'B	111.4
C1—N1—C1'	8.8 (10)	C5'—C4'—H4'B	111.4
C1—N1—C5'	120.5 (7)	H4'A—C4'—H4'B	109.2
C1'—N1—C5'	124.8 (7)	N1—C5'—C4'	101.6 (8)
C1—N1—C2'	124.2 (7)	N1—C5'—H5'A	111.5
C1'—N1—C2'	119.6 (7)	C4'—C5'—H5'A	111.5
C5'—N1—C2'	115.3 (6)	N1—C5'—H5'B	111.5
C1—N1—C2	124.6 (6)	C4'—C5'—H5'B	111.5
C1'—N1—C2	119.8 (7)	H5'A—C5'—H5'B	109.3
C5'—N1—C2	114.9 (6)	N2—C6—S4	126.4 (5)
C2'—N1—C2	1.5 (13)	N2—C6—S3	112.7 (5)
C1—N1—C5	126.7 (6)	S4—C6—S3	119.8 (4)
C1'—N1—C5	131.7 (7)	N2—C7—C8	102.4 (7)
C5'—N1—C5	8.1 (8)	N2—C7—H7A	111.3
C2'—N1—C5	108.7 (6)	C8—C7—H7A	111.3
C2—N1—C5	108.4 (5)	N2—C7—H7B	111.3
C6—N2—C6'	10.3 (7)	C8—C7—H7B	111.3
C6—N2—C7'	119.5 (6)	H7A—C7—H7B	109.2
C6'—N2—C7'	122.4 (7)	C9—C8—C7	104.1 (7)
C6—N2—C10'	127.7 (6)	C9—C8—H8A	110.9
C6'—N2—C10'	124.3 (7)	C7—C8—H8A	110.9
C7'—N2—C10'	112.7 (6)	C9—C8—H8B	110.9
C6—N2—C10	127.1 (5)	C7—C8—H8B	110.9
C6'—N2—C10	124.5 (6)	H8A—C8—H8B	109.0
C7'—N2—C10	113.0 (6)	C8—C9—C10	103.3 (7)
C10'—N2—C10	3.8 (12)	C8—C9—H9A	111.1
C6—N2—C7	121.5 (5)	C10—C9—H9A	111.1
C6'—N2—C7	124.1 (6)	C8—C9—H9B	111.1
C7'—N2—C7	2.3 (9)	C10—C9—H9B	111.1
C10'—N2—C7	110.8 (6)	H9A—C9—H9B	109.1
C10—N2—C7	111.1 (5)	N2—C10—C9	101.5 (6)
N1—C1—S2	120.9 (7)	N2—C10—H10A	111.5
N1—C1—S1	115.1 (7)	C9—C10—H10A	111.5
S2—C1—S1	123.6 (6)	N2—C10—H10B	111.5
N1—C2—C3	105.8 (7)	C9—C10—H10B	111.5
N1—C2—H2A	110.6	H10A—C10—H10B	109.3
C3—C2—H2A	110.6	N2—C6'—S4	118.6 (7)
N1—C2—H2B	110.6	N2—C6'—S3	111.9 (7)
C3—C2—H2B	110.6	S4—C6'—S3	127.1 (6)
H2A—C2—H2B	108.7	N2—C7'—C8'	102.7 (8)
C4—C3—C2	104.3 (7)	N2—C7'—H7'A	111.2
C4—C3—H3A	110.9	C8'—C7'—H7'A	111.2
C2—C3—H3A	110.9	N2—C7'—H7'B	111.2
C4—C3—H3B	110.9	C8'—C7'—H7'B	111.2
C2—C3—H3B	110.9	H7'A—C7'—H7'B	109.1
H3A—C3—H3B	108.9	C9'—C8'—C7'	105.2 (9)
C3—C4—C5	101.8 (7)	C9'—C8'—H8'A	110.7
C3—C4—H4A	111.4	C7'—C8'—H8'A	110.7
C5—C4—H4A	111.4	C9'—C8'—H8'B	110.7
C3—C4—H4B	111.4	C7'—C8'—H8'B	110.7
C5—C4—H4B	111.4	H8'A—C8'—H8'B	108.8
H4A—C4—H4B	109.3	C8'—C9'—C10'	102.2 (9)
N1—C5—C4	104.6 (6)	C8'—C9'—H9'A	111.3
N1—C5—H5A	110.8	C10'—C9'—H9'A	111.3
C4—C5—H5A	110.8	C8'—C9'—H9'B	111.3
N1—C5—H5B	110.8	C10'—C9'—H9'B	111.3
C4—C5—H5B	110.8	H9'A—C9'—H9'B	109.2
H5A—C5—H5B	108.9	N2—C10'—C9'	103.7 (9)
N1—C1'—S2	124.3 (9)	N2—C10'—H10C	111.0
N1—C1'—S1	105.3 (8)	C9'—C10'—H10C	111.0
S2—C1'—S1	128.8 (8)	N2—C10'—H10D	111.0
N1—C2'—C3'	101.0 (8)	C9'—C10'—H10D	111.0
N1—C2'—H2'A	111.6	H10C—C10'—H10D	109.0
C3'—C2'—H2'A	111.6	S3—C11—S1	114.05 (18)
N1—C2'—H2'B	111.6	S3—C11—H11A	108.7
C3'—C2'—H2'B	111.6	S1—C11—H11A	108.7
H2'A—C2'—H2'B	109.4	S3—C11—H11B	108.7
C4'—C3'—C2'	102.0 (9)	S1—C11—H11B	108.7
C4'—C3'—H3'A	111.4	H11A—C11—H11B	107.6
C1'—N1—C1—S2	52 (6)	C10'—N2—C6—S4	172.3 (10)
C5'—N1—C1—S2	173.4 (8)	C10—N2—C6—S4	177.1 (8)
C2'—N1—C1—S2	−8.8 (15)	C7—N2—C6—S4	−9.9 (11)
C2—N1—C1—S2	−7.1 (13)	C6'—N2—C6—S3	−70 (4)
C5—N1—C1—S2	179.6 (7)	C7'—N2—C6—S3	−179.6 (10)
C1'—N1—C1—S1	−120 (7)	C10'—N2—C6—S3	4.0 (12)
C5'—N1—C1—S1	0.9 (12)	C10—N2—C6—S3	8.7 (10)
C2'—N1—C1—S1	178.7 (10)	C7—N2—C6—S3	−178.2 (7)
C2—N1—C1—S1	−179.6 (8)	C6'—S4—C6—N2	−114 (4)
C5—N1—C1—S1	7.1 (12)	C6'—S4—C6—S3	54 (3)
C1'—S2—C1—N1	−95 (7)	C6'—S3—C6—N2	106 (4)
C1'—S2—C1—S1	77 (7)	C11—S3—C6—N2	172.9 (4)
C1'—S1—C1—N1	126 (6)	C6'—S3—C6—S4	−63 (4)
C11—S1—C1—N1	173.6 (7)	C11—S3—C6—S4	3.7 (5)
C1'—S1—C1—S2	−47 (6)	C6—N2—C7—C8	−164.2 (6)
C11—S1—C1—S2	1.4 (8)	C6'—N2—C7—C8	−176.1 (7)
C1—N1—C2—C3	−166.2 (8)	C7'—N2—C7—C8	−133 (32)
C1'—N1—C2—C3	−174.8 (9)	C10'—N2—C7—C8	13.9 (13)
C5'—N1—C2—C3	13.3 (13)	C10—N2—C7—C8	9.8 (12)
C2'—N1—C2—C3	−93 (32)	N2—C7—C8—C9	−32.0 (10)
C5—N1—C2—C3	8.1 (11)	C7—C8—C9—C10	42.8 (10)
N1—C2—C3—C4	−29.8 (11)	C6—N2—C10—C9	−170.8 (6)
C2—C3—C4—C5	38.6 (10)	C6'—N2—C10—C9	−158.5 (7)
C1—N1—C5—C4	−169.9 (8)	C7'—N2—C10—C9	17.1 (13)
C1'—N1—C5—C4	−160.6 (9)	C10'—N2—C10—C9	−70 (11)
C5'—N1—C5—C4	−128 (7)	C7—N2—C10—C9	15.6 (11)
C2'—N1—C5—C4	17.5 (11)	C8—C9—C10—N2	−35.2 (10)
C2—N1—C5—C4	15.9 (10)	C6—N2—C6'—S4	−66 (4)
C3—C4—C5—N1	−33.6 (9)	C7'—N2—C6'—S4	10.4 (13)
C1—N1—C1'—S2	−116 (7)	C10'—N2—C6'—S4	−179.0 (9)
C5'—N1—C1'—S2	−179.4 (10)	C10—N2—C6'—S4	−174.4 (8)
C2'—N1—C1'—S2	7.9 (17)	C7—N2—C6'—S4	12.3 (12)
C2—N1—C1'—S2	9.6 (16)	C6—N2—C6'—S3	97 (4)
C5—N1—C1'—S2	−174.2 (8)	C7'—N2—C6'—S3	174.0 (10)
C1—N1—C1'—S1	51 (6)	C10'—N2—C6'—S3	−15.4 (12)
C5'—N1—C1'—S1	−12.6 (13)	C10—N2—C6'—S3	−10.8 (11)
C2'—N1—C1'—S1	174.7 (10)	C7—N2—C6'—S3	175.9 (8)
C2—N1—C1'—S1	176.4 (8)	C6—S4—C6'—N2	49 (3)
C5—N1—C1'—S1	−7.3 (14)	C6—S4—C6'—S3	−111 (4)
C1—S2—C1'—N1	73 (7)	C11—S3—C6'—N2	−174.7 (6)
C1—S2—C1'—S1	−91 (7)	C6—S3—C6'—N2	−60 (4)
C1—S1—C1'—N1	−45 (5)	C11—S3—C6'—S4	−12.9 (7)
C11—S1—C1'—N1	−177.6 (7)	C6—S3—C6'—S4	102 (4)
C1—S1—C1'—S2	121 (7)	C6—N2—C7'—C8'	170.5 (8)
C11—S1—C1'—S2	−11.6 (12)	C6'—N2—C7'—C8'	159.0 (8)
C1—N1—C2'—C3'	166.3 (8)	C10'—N2—C7'—C8'	−12.6 (16)
C1'—N1—C2'—C3'	157.5 (10)	C10—N2—C7'—C8'	−16.7 (15)
C5'—N1—C2'—C3'	−15.8 (15)	C7—N2—C7'—C8'	21 (30)
C2—N1—C2'—C3'	59 (31)	N2—C7'—C8'—C9'	31.1 (14)
C5—N1—C2'—C3'	−20.9 (13)	C7'—C8'—C9'—C10'	−37.1 (14)
N1—C2'—C3'—C4'	35.6 (13)	C6—N2—C10'—C9'	166.5 (7)
C2'—C3'—C4'—C5'	−42.5 (12)	C6'—N2—C10'—C9'	178.5 (7)
C1—N1—C5'—C4'	167.5 (8)	C7'—N2—C10'—C9'	−10.1 (15)
C1'—N1—C5'—C4'	176.6 (9)	C10—N2—C10'—C9'	84 (11)
C2'—N1—C5'—C4'	−10.5 (14)	C7—N2—C10'—C9'	−11.4 (14)
C2—N1—C5'—C4'	−12.0 (12)	C8'—C9'—C10'—N2	28.7 (13)
C5—N1—C5'—C4'	26 (6)	C6'—S3—C11—S1	84.1 (4)
C3'—C4'—C5'—N1	32.6 (11)	C6—S3—C11—S1	76.5 (3)
C6'—N2—C6—S4	98 (4)	C1—S1—C11—S3	79.2 (4)
C7'—N2—C6—S4	−11.3 (12)	C1'—S1—C11—S3	84.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···S3i	0.99	2.89	3.811 (9)	155
C10—H10B···S4ii	0.99	2.99	3.699 (11)	130
C9—H9A···S1ii	0.99	2.87	3.740 (8)	147
C9'—H9'A···S1ii	0.99	3.50	4.209 (11)	131
C5'—H5'B···S2i	0.99	2.94	3.704 (14)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯S3i	0.99	2.89	3.811 (9)	155
C10—H10B⋯S4ii	0.99	2.99	3.699 (11)	130
C9—H9A⋯S1ii	0.99	2.87	3.740 (8)	147
C9′—H9′A⋯S1ii	0.99	3.50	4.209 (11)	131
C5′—H5′B⋯S2i	0.99	2.94	3.704 (14)	137

Symmetry codes: (i) ; (ii) .