Crystal structures of (N-methyl-N-phenyl­amino)(N-methyl-N-phenyl­carbamoyl)sulfide and the corresponding disulfane

(N-Methyl-N-phenyl­carbamoyl)(N-methyl-N-phenyl­amino)sulfide and the corresponding disulfane are stable derivatives of (chloro­carbon­yl)sulfenyl chloride and (chloro­carbon­yl)disulfanyl chloride, respectively.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.067
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Datablock: I

No errors found in this datablock




Datablock: II


Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         20 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

For both compounds, data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) (N-Methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide

Crystal data

C15H16N2OS	F(000) = 288
Mr = 272.36	Dx = 1.307 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 9.0682 (7) Å	Cell parameters from 2915 reflections
b = 6.8402 (5) Å	θ = 2.3–27.4°
c = 11.4686 (9) Å	µ = 0.23 mm^−1
β = 103.349 (1)°	T = 173 K
V = 692.16 (9) Å^3	Plate, colourless
Z = 2	0.40 × 0.35 × 0.12 mm

Data collection

Bruker SMART APEXII diffractometer	2961 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.022
Absorption correction: multi-scan (SADABS; Bruker, 2002)	θmax = 27.4°, θmin = 1.8°
Tmin = 0.687, Tmax = 0.746	h = −11→11
8061 measured reflections	k = −8→8
3145 independent reflections	l = −14→14

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0297P)^2 + 0.1164P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.067	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.19 e Å^−3
3145 reflections	Δρmin = −0.15 e Å^−3
174 parameters	Absolute structure: Flack x determined using 1285 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.05 (3)

Special details

Geometry. All e.s.d.'s 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.32124 (5)	0.41906 (8)	0.67886 (4)	0.02848 (13)
O1	0.41605 (17)	0.0518 (2)	0.71103 (13)	0.0314 (3)
N1	0.2797 (2)	0.1212 (3)	0.52292 (15)	0.0265 (4)
N2	0.39549 (17)	0.4094 (3)	0.82703 (13)	0.0264 (3)
C1	0.2020 (2)	0.2644 (3)	0.43921 (17)	0.0248 (4)
C2	0.2834 (2)	0.3936 (4)	0.38553 (17)	0.0289 (5)
H2A	0.3910	0.3938	0.4080	0.035*
C3	0.2080 (3)	0.5227 (3)	0.2990 (2)	0.0352 (5)
H3A	0.2637	0.6114	0.2619	0.042*
C4	0.0517 (3)	0.5218 (4)	0.2669 (2)	0.0383 (6)
H4A	−0.0001	0.6109	0.2079	0.046*
C5	−0.0302 (2)	0.3922 (4)	0.31988 (19)	0.0391 (6)
H5A	−0.1378	0.3926	0.2972	0.047*
C6	0.0446 (2)	0.2620 (4)	0.40601 (19)	0.0317 (5)
H6A	−0.0112	0.1719	0.4420	0.038*
C7	0.2839 (2)	−0.0795 (4)	0.47987 (18)	0.0317 (4)
H7A	0.3168	−0.1675	0.5483	0.048*
H7B	0.3553	−0.0877	0.4276	0.048*
H7C	0.1826	−0.1176	0.4348	0.048*
C8	0.3469 (2)	0.1659 (3)	0.63758 (18)	0.0247 (4)
C9	0.3038 (3)	0.3084 (4)	0.8984 (2)	0.0330 (5)
H9A	0.3380	0.3467	0.9827	0.050*
H9B	0.3151	0.1668	0.8911	0.050*
H9C	0.1970	0.3443	0.8691	0.050*
C10	0.5557 (2)	0.4074 (4)	0.86869 (15)	0.0248 (4)
C11	0.6441 (3)	0.5337 (4)	0.81829 (18)	0.0317 (5)
H11A	0.5971	0.6177	0.7545	0.038*
C12	0.8000 (3)	0.5379 (4)	0.8604 (2)	0.0364 (5)
H12A	0.8592	0.6238	0.8248	0.044*
C13	0.8703 (2)	0.4179 (5)	0.95412 (18)	0.0363 (5)
H13A	0.9774	0.4200	0.9825	0.044*
C14	0.7824 (3)	0.2954 (4)	1.0056 (2)	0.0357 (5)
H14A	0.8297	0.2139	1.0706	0.043*
C15	0.6264 (3)	0.2891 (3)	0.9641 (2)	0.0306 (5)
H15A	0.5676	0.2041	1.0008	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0321 (2)	0.0234 (2)	0.0263 (2)	0.0027 (2)	−0.00070 (17)	−0.0012 (2)
O1	0.0339 (8)	0.0284 (8)	0.0284 (8)	0.0061 (6)	0.0002 (6)	0.0003 (7)
N1	0.0291 (9)	0.0245 (9)	0.0240 (8)	−0.0005 (7)	0.0019 (7)	−0.0019 (7)
N2	0.0278 (8)	0.0279 (8)	0.0232 (7)	−0.0030 (9)	0.0053 (6)	−0.0007 (9)
C1	0.0266 (10)	0.0259 (10)	0.0207 (10)	0.0016 (8)	0.0031 (8)	−0.0037 (8)
C2	0.0283 (10)	0.0291 (13)	0.0273 (9)	−0.0012 (9)	0.0021 (8)	−0.0029 (9)
C3	0.0461 (13)	0.0285 (12)	0.0294 (11)	−0.0029 (10)	0.0054 (10)	−0.0002 (9)
C4	0.0475 (14)	0.0365 (13)	0.0268 (11)	0.0149 (11)	−0.0002 (10)	0.0002 (10)
C5	0.0275 (10)	0.0534 (17)	0.0340 (11)	0.0107 (12)	0.0024 (8)	−0.0059 (12)
C6	0.0253 (10)	0.0419 (13)	0.0285 (11)	0.0011 (9)	0.0075 (8)	−0.0026 (9)
C7	0.0364 (10)	0.0276 (9)	0.0309 (10)	0.0006 (12)	0.0073 (8)	−0.0040 (12)
C8	0.0222 (9)	0.0231 (10)	0.0287 (10)	−0.0003 (8)	0.0059 (8)	−0.0021 (8)
C9	0.0323 (11)	0.0330 (12)	0.0355 (12)	−0.0054 (10)	0.0115 (9)	−0.0031 (10)
C10	0.0292 (9)	0.0252 (9)	0.0197 (8)	−0.0028 (10)	0.0049 (7)	−0.0053 (9)
C11	0.0363 (11)	0.0364 (12)	0.0218 (10)	−0.0061 (10)	0.0055 (9)	0.0016 (9)
C12	0.0351 (12)	0.0457 (14)	0.0302 (11)	−0.0135 (11)	0.0115 (10)	−0.0034 (10)
C13	0.0286 (10)	0.0442 (12)	0.0348 (10)	−0.0034 (13)	0.0045 (8)	−0.0094 (14)
C14	0.0363 (12)	0.0343 (11)	0.0322 (12)	0.0010 (10)	−0.0007 (9)	0.0006 (10)
C15	0.0345 (11)	0.0261 (10)	0.0307 (11)	−0.0027 (10)	0.0069 (9)	0.0017 (9)

Geometric parameters (Å, º)

S1—N2	1.6784 (15)	C6—H6A	0.9500
S1—C8	1.824 (2)	C7—H7A	0.9800
O1—C8	1.212 (3)	C7—H7B	0.9800
N1—C8	1.351 (3)	C7—H7C	0.9800
N1—C1	1.437 (3)	C9—H9A	0.9800
N1—C7	1.462 (3)	C9—H9B	0.9800
N2—C10	1.421 (2)	C9—H9C	0.9800
N2—C9	1.467 (3)	C10—C11	1.392 (3)
C1—C2	1.383 (3)	C10—C15	1.393 (3)
C1—C6	1.390 (3)	C11—C12	1.385 (3)
C2—C3	1.385 (3)	C11—H11A	0.9500
C2—H2A	0.9500	C12—C13	1.385 (4)
C3—C4	1.380 (3)	C12—H12A	0.9500
C3—H3A	0.9500	C13—C14	1.379 (4)
C4—C5	1.384 (4)	C13—H13A	0.9500
C4—H4A	0.9500	C14—C15	1.385 (3)
C5—C6	1.386 (3)	C14—H14A	0.9500
C5—H5A	0.9500	C15—H15A	0.9500
N2—S1—C8	100.36 (10)	H7A—C7—H7C	109.5
C8—N1—C1	122.48 (18)	H7B—C7—H7C	109.5
C8—N1—C7	120.04 (17)	O1—C8—N1	125.12 (19)
C1—N1—C7	117.48 (16)	O1—C8—S1	120.52 (16)
C10—N2—C9	118.37 (17)	N1—C8—S1	114.34 (15)
C10—N2—S1	118.74 (12)	N2—C9—H9A	109.5
C9—N2—S1	115.90 (14)	N2—C9—H9B	109.5
C2—C1—C6	120.34 (19)	H9A—C9—H9B	109.5
C2—C1—N1	120.23 (18)	N2—C9—H9C	109.5
C6—C1—N1	119.25 (19)	H9A—C9—H9C	109.5
C1—C2—C3	120.05 (19)	H9B—C9—H9C	109.5
C1—C2—H2A	120.0	C11—C10—C15	118.84 (18)
C3—C2—H2A	120.0	C11—C10—N2	119.8 (2)
C4—C3—C2	119.7 (2)	C15—C10—N2	121.28 (19)
C4—C3—H3A	120.2	C12—C11—C10	120.5 (2)
C2—C3—H3A	120.2	C12—C11—H11A	119.8
C3—C4—C5	120.5 (2)	C10—C11—H11A	119.8
C3—C4—H4A	119.7	C11—C12—C13	120.6 (2)
C5—C4—H4A	119.7	C11—C12—H12A	119.7
C4—C5—C6	120.1 (2)	C13—C12—H12A	119.7
C4—C5—H5A	120.0	C14—C13—C12	118.91 (19)
C6—C5—H5A	120.0	C14—C13—H13A	120.5
C5—C6—C1	119.4 (2)	C12—C13—H13A	120.5
C5—C6—H6A	120.3	C13—C14—C15	121.1 (2)
C1—C6—H6A	120.3	C13—C14—H14A	119.4
N1—C7—H7A	109.5	C15—C14—H14A	119.4
N1—C7—H7B	109.5	C14—C15—C10	120.0 (2)
H7A—C7—H7B	109.5	C14—C15—H15A	120.0
N1—C7—H7C	109.5	C10—C15—H15A	120.0
C8—S1—N2—C10	77.3 (2)	C1—N1—C8—S1	3.3 (2)
C8—S1—N2—C9	−73.05 (18)	C7—N1—C8—S1	−176.52 (14)
C8—N1—C1—C2	78.2 (3)	N2—S1—C8—O1	−6.02 (19)
C7—N1—C1—C2	−101.9 (2)	N2—S1—C8—N1	172.19 (14)
C8—N1—C1—C6	−106.6 (2)	C9—N2—C10—C11	−166.6 (2)
C7—N1—C1—C6	73.2 (2)	S1—N2—C10—C11	43.8 (3)
C6—C1—C2—C3	0.6 (3)	C9—N2—C10—C15	9.7 (3)
N1—C1—C2—C3	175.69 (19)	S1—N2—C10—C15	−139.90 (19)
C1—C2—C3—C4	0.1 (3)	C15—C10—C11—C12	1.6 (3)
C2—C3—C4—C5	−0.4 (3)	N2—C10—C11—C12	178.0 (2)
C3—C4—C5—C6	0.0 (4)	C10—C11—C12—C13	−0.6 (4)
C4—C5—C6—C1	0.6 (3)	C11—C12—C13—C14	−0.6 (4)
C2—C1—C6—C5	−0.9 (3)	C12—C13—C14—C15	0.8 (4)
N1—C1—C6—C5	−176.1 (2)	C13—C14—C15—C10	0.2 (4)
C1—N1—C8—O1	−178.6 (2)	C11—C10—C15—C14	−1.4 (3)
C7—N1—C8—O1	1.6 (3)	N2—C10—C15—C14	−177.7 (2)

(II) (N-Methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)disulfane

Crystal data

C15H16N2OS2	F(000) = 640
Mr = 304.42	Dx = 1.375 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.0414 (17) Å	Cell parameters from 2950 reflections
b = 5.5023 (6) Å	θ = 3.1–27.5°
c = 17.2986 (19) Å	µ = 0.36 mm^−1
β = 105.564 (1)°	T = 123 K
V = 1470.9 (3) Å^3	Block, colorless
Z = 4	0.41 × 0.18 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	3033 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.024
φ and ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −20→20
Tmin = 0.699, Tmax = 0.746	k = −7→7
16044 measured reflections	l = −22→22
3355 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0301P)^2 + 0.7728P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3355 reflections	Δρmax = 0.32 e Å^−3
183 parameters	Δρmin = −0.22 e Å^−3

Special details

Geometry. All e.s.d.'s 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.24264 (2)	0.27366 (6)	0.12829 (2)	0.01720 (9)
S2	0.27516 (2)	0.52421 (6)	0.05260 (2)	0.01821 (9)
O1	0.15803 (6)	0.07736 (18)	−0.01294 (5)	0.0215 (2)
N1	0.12052 (7)	−0.0673 (2)	0.09646 (6)	0.0173 (2)
N2	0.36329 (7)	0.4255 (2)	0.02877 (6)	0.0184 (2)
C1	0.12310 (8)	−0.0405 (2)	0.18005 (7)	0.0160 (2)
C2	0.16345 (8)	−0.2156 (2)	0.23508 (8)	0.0199 (3)
H2A	0.1907	−0.3512	0.2182	0.024*
C3	0.16379 (9)	−0.1914 (3)	0.31517 (8)	0.0232 (3)
H3A	0.1907	−0.3119	0.3530	0.028*
C4	0.12493 (9)	0.0083 (3)	0.33984 (8)	0.0227 (3)
H4A	0.1266	0.0268	0.3948	0.027*
C5	0.08363 (9)	0.1808 (3)	0.28448 (8)	0.0239 (3)
H5A	0.0565	0.3166	0.3015	0.029*
C6	0.08171 (8)	0.1558 (2)	0.20413 (8)	0.0209 (3)
H6A	0.0523	0.2721	0.1659	0.025*
C7	0.06129 (8)	−0.2499 (2)	0.05015 (8)	0.0204 (3)
H7A	0.0626	−0.2431	−0.0061	0.031*
H7B	0.0024	−0.2168	0.0537	0.031*
H7C	0.0792	−0.4118	0.0719	0.031*
C8	0.16585 (8)	0.0771 (2)	0.05874 (7)	0.0163 (2)
C9	0.34991 (9)	0.2336 (3)	−0.03205 (8)	0.0233 (3)
H9A	0.3968	0.2384	−0.0585	0.035*
H9B	0.2943	0.2589	−0.0720	0.035*
H9C	0.3497	0.0750	−0.0063	0.035*
C10	0.44464 (8)	0.4352 (2)	0.08806 (7)	0.0168 (2)
C11	0.50700 (9)	0.2568 (2)	0.09139 (8)	0.0219 (3)
H11A	0.4951	0.1250	0.0546	0.026*
C12	0.58679 (9)	0.2706 (3)	0.14843 (9)	0.0256 (3)
H12A	0.6291	0.1485	0.1500	0.031*
C13	0.60500 (9)	0.4600 (3)	0.20266 (8)	0.0242 (3)
H13A	0.6594	0.4686	0.2416	0.029*
C14	0.54283 (9)	0.6379 (3)	0.19970 (8)	0.0228 (3)
H14A	0.5548	0.7683	0.2371	0.027*
C15	0.46357 (9)	0.6273 (2)	0.14279 (8)	0.0202 (3)
H15A	0.4219	0.7512	0.1410	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01726 (16)	0.01986 (16)	0.01529 (15)	−0.00238 (11)	0.00576 (12)	−0.00051 (11)
S2	0.01769 (16)	0.01601 (16)	0.02234 (16)	0.00171 (11)	0.00784 (12)	0.00252 (12)
O1	0.0234 (5)	0.0262 (5)	0.0148 (4)	−0.0021 (4)	0.0049 (4)	0.0012 (4)
N1	0.0179 (5)	0.0187 (5)	0.0158 (5)	−0.0033 (4)	0.0055 (4)	−0.0012 (4)
N2	0.0170 (5)	0.0226 (6)	0.0175 (5)	−0.0012 (4)	0.0079 (4)	−0.0021 (4)
C1	0.0150 (6)	0.0183 (6)	0.0159 (6)	−0.0029 (5)	0.0063 (4)	−0.0013 (5)
C2	0.0203 (6)	0.0192 (6)	0.0208 (6)	0.0021 (5)	0.0066 (5)	−0.0011 (5)
C3	0.0234 (7)	0.0254 (7)	0.0192 (6)	0.0008 (5)	0.0030 (5)	0.0033 (5)
C4	0.0231 (7)	0.0293 (7)	0.0177 (6)	−0.0064 (5)	0.0088 (5)	−0.0050 (5)
C5	0.0269 (7)	0.0203 (7)	0.0299 (7)	−0.0006 (5)	0.0168 (6)	−0.0042 (5)
C6	0.0211 (6)	0.0193 (6)	0.0251 (7)	0.0025 (5)	0.0110 (5)	0.0037 (5)
C7	0.0197 (6)	0.0204 (6)	0.0198 (6)	−0.0034 (5)	0.0031 (5)	−0.0009 (5)
C8	0.0144 (6)	0.0161 (6)	0.0181 (6)	0.0020 (5)	0.0039 (5)	0.0013 (5)
C9	0.0211 (6)	0.0322 (8)	0.0173 (6)	−0.0031 (5)	0.0064 (5)	−0.0068 (5)
C10	0.0177 (6)	0.0185 (6)	0.0165 (6)	−0.0035 (5)	0.0087 (5)	0.0004 (5)
C11	0.0235 (7)	0.0204 (7)	0.0225 (6)	−0.0008 (5)	0.0074 (5)	−0.0064 (5)
C12	0.0212 (7)	0.0255 (7)	0.0295 (7)	0.0026 (5)	0.0056 (6)	−0.0049 (6)
C13	0.0198 (6)	0.0292 (7)	0.0228 (7)	−0.0040 (5)	0.0042 (5)	−0.0027 (6)
C14	0.0264 (7)	0.0220 (7)	0.0218 (6)	−0.0060 (5)	0.0098 (5)	−0.0069 (5)
C15	0.0226 (6)	0.0177 (6)	0.0230 (6)	−0.0014 (5)	0.0106 (5)	−0.0023 (5)

Geometric parameters (Å, º)

S1—C8	1.8273 (13)	C6—H6A	0.9500
S1—S2	2.0625 (5)	C7—H7A	0.9800
S2—N2	1.6660 (11)	C7—H7B	0.9800
O1—C8	1.2123 (15)	C7—H7C	0.9800
N1—C8	1.3569 (16)	C9—H9A	0.9800
N1—C1	1.4429 (15)	C9—H9B	0.9800
N1—C7	1.4646 (16)	C9—H9C	0.9800
N2—C10	1.4281 (16)	C10—C11	1.3917 (18)
N2—C9	1.4656 (16)	C10—C15	1.3967 (18)
C1—C2	1.3865 (18)	C11—C12	1.3929 (19)
C1—C6	1.3888 (18)	C11—H11A	0.9500
C2—C3	1.3905 (18)	C12—C13	1.3800 (19)
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.386 (2)	C13—C14	1.388 (2)
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.384 (2)	C14—C15	1.3847 (19)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.3888 (18)	C15—H15A	0.9500
C5—H5A	0.9500
C8—S1—S2	102.60 (4)	H7A—C7—H7C	109.5
N2—S2—S1	108.37 (4)	H7B—C7—H7C	109.5
C8—N1—C1	123.17 (10)	O1—C8—N1	124.80 (12)
C8—N1—C7	119.43 (10)	O1—C8—S1	122.64 (10)
C1—N1—C7	117.28 (10)	N1—C8—S1	112.55 (9)
C10—N2—C9	118.17 (11)	N2—C9—H9A	109.5
C10—N2—S2	118.86 (8)	N2—C9—H9B	109.5
C9—N2—S2	116.23 (8)	H9A—C9—H9B	109.5
C2—C1—C6	120.47 (11)	N2—C9—H9C	109.5
C2—C1—N1	119.97 (11)	H9A—C9—H9C	109.5
C6—C1—N1	119.51 (11)	H9B—C9—H9C	109.5
C1—C2—C3	119.60 (12)	C11—C10—C15	118.84 (12)
C1—C2—H2A	120.2	C11—C10—N2	120.77 (11)
C3—C2—H2A	120.2	C15—C10—N2	120.38 (12)
C4—C3—C2	120.05 (13)	C10—C11—C12	120.30 (12)
C4—C3—H3A	120.0	C10—C11—H11A	119.8
C2—C3—H3A	120.0	C12—C11—H11A	119.8
C5—C4—C3	120.12 (12)	C13—C12—C11	120.62 (13)
C5—C4—H4A	119.9	C13—C12—H12A	119.7
C3—C4—H4A	119.9	C11—C12—H12A	119.7
C4—C5—C6	120.16 (12)	C12—C13—C14	119.24 (13)
C4—C5—H5A	119.9	C12—C13—H13A	120.4
C6—C5—H5A	119.9	C14—C13—H13A	120.4
C1—C6—C5	119.55 (12)	C15—C14—C13	120.65 (12)
C1—C6—H6A	120.2	C15—C14—H14A	119.7
C5—C6—H6A	120.2	C13—C14—H14A	119.7
N1—C7—H7A	109.5	C14—C15—C10	120.34 (12)
N1—C7—H7B	109.5	C14—C15—H15A	119.8
H7A—C7—H7B	109.5	C10—C15—H15A	119.8
N1—C7—H7C	109.5
S1—S2—N2—C10	−72.86 (10)	C7—N1—C8—S1	−175.04 (9)
S1—S2—N2—C9	77.90 (9)	C8—S1—S2—N2	−92.62 (6)
C8—N1—C1—C2	−110.35 (14)	S2—S1—C8—O1	15.13 (12)
C7—N1—C1—C2	73.77 (15)	S2—S1—C8—N1	−165.53 (8)
C8—N1—C1—C6	72.46 (16)	C9—N2—C10—C11	−4.59 (17)
C7—N1—C1—C6	−103.41 (14)	S2—N2—C10—C11	145.60 (11)
C6—C1—C2—C3	−1.25 (19)	C9—N2—C10—C15	174.12 (11)
N1—C1—C2—C3	−178.41 (12)	S2—N2—C10—C15	−35.69 (15)
C1—C2—C3—C4	−0.8 (2)	C15—C10—C11—C12	−0.02 (19)
C2—C3—C4—C5	1.8 (2)	N2—C10—C11—C12	178.70 (12)
C3—C4—C5—C6	−0.6 (2)	C10—C11—C12—C13	0.4 (2)
C2—C1—C6—C5	2.36 (19)	C11—C12—C13—C14	−0.2 (2)
N1—C1—C6—C5	179.54 (12)	C12—C13—C14—C15	−0.4 (2)
C4—C5—C6—C1	−1.4 (2)	C13—C14—C15—C10	0.8 (2)
C1—N1—C8—O1	−171.52 (12)	C11—C10—C15—C14	−0.56 (19)
C7—N1—C8—O1	4.27 (19)	N2—C10—C15—C14	−179.29 (11)
C1—N1—C8—S1	9.16 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···S1^i	0.95	2.84	3.766 (1)	165
C7—H7B···O1^ii	0.98	2.60	3.532 (2)	160

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z.