A co-crystal of 3-(3,5-dinitro-benzo-yl)-1,1-dimethyl-thio-urea and N,N-dimethyl-3,5-dinitro-benzamide.

In the title compound, C(10)H(10)N(4)O(5)S·C(9)H(9)N(3)O(5), the amide groups of 3-(3,5-dinitro-benzo-yl)-1,1-dimethyl-thio-urea and N,N-dimethyl-3,5-dinitro-benzamide mol-ecules are oriented at dihedral angles of 39.13 (8) and 55.97 (11)°, respectively, to the attached benzene rings. In the crystal, the two mol-ecules are linked by an N-H⋯O hydrogen bond. Weak C-H⋯O link the mol-ecules into a sheet parallel to the bc plane. C-H⋯S inter-actions also occur.

Related literature

For related structures, see: Saeed et al. (2010a ▶,b ▶, 2011 ▶, 2012 ▶).

Experimental

Crystal data

C10H10N4O5S·C9H9N3O5

M = 537.47

Triclinic,

a = 9.8457 (5) Å

b = 10.0057 (5) Å

c = 12.5185 (6) Å

α = 72.413 (5)°

β = 78.428 (4)°

γ = 89.129 (4)°

V = 1150.35 (10) Å3

Z = 2

Cu Kα radiation

μ = 1.90 mm−1

T = 123 K

0.44 × 0.38 × 0.27 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011 ▶) T min = 0.488, T max = 0.628

7591 measured reflections

4597 independent reflections

4099 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.07

4597 reflections

342 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041864/xu5627sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041864/xu5627Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041864/xu5627Isup3.cml

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

C10H10N4O5S·C9H9N3O5	Z = 2
Mr = 537.47	F(000) = 556
Triclinic, P1	Dx = 1.552 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.8457 (5) Å	Cell parameters from 4858 reflections
b = 10.0057 (5) Å	θ = 3.7–75.6°
c = 12.5185 (6) Å	µ = 1.90 mm−1
α = 72.413 (5)°	T = 123 K
β = 78.428 (4)°	Prism, colorless
γ = 89.129 (4)°	0.44 × 0.38 × 0.27 mm
V = 1150.35 (10) Å3

Agilent Xcalibur Ruby Gemini diffractometer	4597 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4099 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 10.5081 pixels mm-1	θmax = 75.7°, θmin = 3.8°
ω scans	h = −8→12
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011)	k = −11→12
Tmin = 0.488, Tmax = 0.628	l = −15→15
7591 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.2475P] where P = (Fo2 + 2Fc2)/3
4597 reflections	(Δ/σ)max = 0.001
342 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.33 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
S1A	0.76619 (4)	0.42766 (5)	0.57712 (3)	0.02502 (12)
O1A	0.78961 (16)	0.65356 (16)	−0.12724 (12)	0.0403 (4)
O2A	0.86851 (15)	0.87002 (14)	−0.18650 (11)	0.0335 (3)
O3A	1.22867 (15)	0.99829 (15)	−0.02521 (12)	0.0390 (3)
O4A	1.27475 (14)	0.85999 (14)	0.13226 (11)	0.0310 (3)
O5A	0.88749 (13)	0.33920 (12)	0.25463 (10)	0.0266 (3)
O1B	0.53210 (19)	0.27963 (15)	0.46302 (12)	0.0459 (4)
O2B	0.40878 (15)	0.24042 (13)	0.35063 (12)	0.0352 (3)
O3B	0.37221 (15)	0.60717 (15)	0.00223 (11)	0.0357 (3)
O4B	0.5129 (2)	0.78858 (17)	−0.05161 (12)	0.0497 (4)
O5B	0.81001 (13)	0.76125 (13)	0.32225 (12)	0.0290 (3)
N1A	0.85641 (16)	0.75121 (16)	−0.12002 (12)	0.0260 (3)
N2A	1.20846 (15)	0.89025 (15)	0.05610 (12)	0.0253 (3)
N3A	0.91130 (14)	0.48145 (14)	0.36539 (11)	0.0199 (3)
N4A	0.94610 (15)	0.26566 (14)	0.49228 (12)	0.0234 (3)
N1B	0.48356 (16)	0.31620 (15)	0.37681 (12)	0.0254 (3)
N2B	0.45895 (16)	0.68028 (16)	0.01822 (12)	0.0260 (3)
N3B	0.63630 (15)	0.91321 (14)	0.30300 (12)	0.0228 (3)
C1A	0.92940 (17)	0.72182 (17)	−0.02373 (13)	0.0212 (3)
C2A	1.03083 (17)	0.81896 (17)	−0.02984 (13)	0.0217 (3)
H2AA	1.0543	0.9010	−0.0937	0.026*
C3A	1.09632 (16)	0.79080 (17)	0.06156 (14)	0.0205 (3)
C4A	1.06124 (16)	0.67505 (16)	0.15829 (13)	0.0195 (3)
H4AA	1.1067	0.6607	0.2207	0.023*
C5A	0.95709 (16)	0.58035 (16)	0.16093 (13)	0.0189 (3)
C6A	0.89257 (16)	0.60135 (17)	0.06793 (13)	0.0204 (3)
H6AA	0.8251	0.5346	0.0676	0.024*
C7A	0.91461 (16)	0.45272 (16)	0.26354 (13)	0.0198 (3)
C8A	0.87935 (17)	0.38376 (17)	0.47537 (13)	0.0202 (3)
C9A	0.9057 (2)	0.14979 (18)	0.59838 (15)	0.0289 (4)
H9AA	0.8141	0.1653	0.6395	0.043*
H9AB	0.9740	0.1450	0.6465	0.043*
H9AC	0.9020	0.0614	0.5803	0.043*
C10A	1.0716 (2)	0.24386 (19)	0.41521 (15)	0.0301 (4)
H10A	1.1132	0.3349	0.3641	0.045*
H10B	1.0474	0.1871	0.3696	0.045*
H10C	1.1382	0.1950	0.4604	0.045*
C1B	0.51644 (17)	0.46087 (16)	0.29998 (13)	0.0197 (3)
C2B	0.47036 (16)	0.49825 (17)	0.19815 (13)	0.0196 (3)
H2BA	0.4193	0.4340	0.1770	0.024*
C3B	0.50307 (17)	0.63468 (17)	0.12917 (13)	0.0206 (3)
C4B	0.57312 (17)	0.73238 (17)	0.15966 (14)	0.0210 (3)
H4BA	0.5926	0.8257	0.1100	0.025*
C5B	0.61429 (16)	0.69075 (17)	0.26466 (14)	0.0196 (3)
C6B	0.58805 (16)	0.55288 (17)	0.33527 (13)	0.0193 (3)
H6BA	0.6183	0.5224	0.4058	0.023*
C7B	0.69378 (17)	0.79193 (17)	0.30051 (13)	0.0209 (3)
C8B	0.7131 (2)	1.01915 (19)	0.32817 (18)	0.0333 (4)
H8BA	0.8121	1.0004	0.3159	0.050*
H8BB	0.6795	1.0162	0.4081	0.050*
H8BC	0.6996	1.1122	0.2775	0.050*
C9B	0.49061 (19)	0.94183 (18)	0.29843 (15)	0.0278 (4)
H9BA	0.4410	0.8558	0.3022	0.042*
H9BB	0.4859	1.0147	0.2267	0.042*
H9BC	0.4476	0.9741	0.3634	0.042*
H1NA	0.889 (2)	0.563 (2)	0.3648 (17)	0.021 (5)*

	U11	U22	U33	U12	U13	U23
S1A	0.0265 (2)	0.0292 (2)	0.0174 (2)	0.00437 (16)	−0.00275 (15)	−0.00549 (16)
O1A	0.0447 (8)	0.0425 (8)	0.0328 (7)	−0.0136 (6)	−0.0189 (6)	−0.0022 (6)
O2A	0.0478 (8)	0.0284 (7)	0.0226 (6)	0.0057 (6)	−0.0134 (6)	−0.0014 (5)
O3A	0.0428 (8)	0.0286 (7)	0.0343 (7)	−0.0168 (6)	−0.0083 (6)	0.0080 (6)
O4A	0.0298 (7)	0.0310 (7)	0.0315 (7)	−0.0068 (5)	−0.0105 (5)	−0.0053 (5)
O5A	0.0364 (7)	0.0172 (6)	0.0253 (6)	−0.0046 (5)	−0.0065 (5)	−0.0044 (5)
O1B	0.0758 (11)	0.0262 (7)	0.0330 (8)	−0.0100 (7)	−0.0259 (7)	0.0051 (6)
O2B	0.0455 (8)	0.0176 (6)	0.0421 (8)	−0.0077 (5)	−0.0112 (6)	−0.0067 (6)
O3B	0.0376 (8)	0.0423 (8)	0.0311 (7)	−0.0024 (6)	−0.0168 (6)	−0.0105 (6)
O4B	0.0754 (12)	0.0413 (9)	0.0241 (7)	−0.0166 (8)	−0.0160 (7)	0.0066 (6)
O5B	0.0251 (6)	0.0239 (6)	0.0426 (7)	0.0021 (5)	−0.0121 (5)	−0.0138 (5)
N1A	0.0293 (8)	0.0276 (8)	0.0197 (7)	0.0010 (6)	−0.0062 (6)	−0.0043 (6)
N2A	0.0241 (7)	0.0215 (7)	0.0262 (7)	−0.0050 (6)	−0.0010 (6)	−0.0037 (6)
N3A	0.0250 (7)	0.0141 (6)	0.0175 (6)	0.0002 (5)	−0.0013 (5)	−0.0023 (5)
N4A	0.0270 (7)	0.0185 (7)	0.0213 (7)	0.0010 (5)	−0.0025 (5)	−0.0028 (6)
N1B	0.0330 (8)	0.0166 (7)	0.0243 (7)	0.0006 (6)	−0.0030 (6)	−0.0049 (6)
N2B	0.0307 (8)	0.0267 (8)	0.0196 (7)	0.0030 (6)	−0.0050 (6)	−0.0061 (6)
N3B	0.0260 (7)	0.0169 (6)	0.0249 (7)	−0.0019 (5)	−0.0044 (5)	−0.0059 (5)
C1A	0.0234 (8)	0.0225 (8)	0.0173 (7)	0.0031 (6)	−0.0045 (6)	−0.0054 (6)
C2A	0.0242 (8)	0.0180 (8)	0.0178 (7)	0.0015 (6)	0.0002 (6)	−0.0009 (6)
C3A	0.0195 (8)	0.0177 (7)	0.0220 (8)	−0.0024 (6)	−0.0008 (6)	−0.0049 (6)
C4A	0.0212 (8)	0.0181 (7)	0.0177 (7)	0.0013 (6)	−0.0031 (6)	−0.0036 (6)
C5A	0.0214 (8)	0.0156 (7)	0.0172 (7)	0.0015 (6)	−0.0006 (6)	−0.0037 (6)
C6A	0.0201 (8)	0.0196 (8)	0.0208 (8)	−0.0004 (6)	−0.0025 (6)	−0.0064 (6)
C7A	0.0202 (8)	0.0162 (7)	0.0201 (8)	−0.0005 (6)	−0.0023 (6)	−0.0025 (6)
C8A	0.0217 (8)	0.0191 (8)	0.0184 (7)	−0.0021 (6)	−0.0043 (6)	−0.0034 (6)
C9A	0.0355 (10)	0.0188 (8)	0.0264 (9)	−0.0012 (7)	−0.0054 (7)	0.0012 (7)
C10A	0.0352 (10)	0.0261 (9)	0.0259 (9)	0.0083 (7)	−0.0038 (7)	−0.0054 (7)
C1B	0.0214 (8)	0.0151 (7)	0.0209 (8)	0.0005 (6)	−0.0012 (6)	−0.0052 (6)
C2B	0.0199 (7)	0.0184 (7)	0.0213 (8)	−0.0014 (6)	−0.0017 (6)	−0.0086 (6)
C3B	0.0215 (8)	0.0224 (8)	0.0174 (7)	0.0004 (6)	−0.0027 (6)	−0.0061 (6)
C4B	0.0217 (8)	0.0166 (7)	0.0212 (8)	−0.0015 (6)	−0.0009 (6)	−0.0027 (6)
C5B	0.0170 (7)	0.0191 (8)	0.0224 (8)	0.0004 (6)	−0.0010 (6)	−0.0080 (6)
C6B	0.0195 (7)	0.0192 (8)	0.0195 (7)	0.0017 (6)	−0.0032 (6)	−0.0067 (6)
C7B	0.0232 (8)	0.0179 (7)	0.0205 (7)	−0.0030 (6)	−0.0027 (6)	−0.0052 (6)
C8B	0.0383 (10)	0.0214 (9)	0.0427 (11)	−0.0042 (7)	−0.0063 (8)	−0.0144 (8)
C9B	0.0321 (9)	0.0213 (8)	0.0295 (9)	0.0072 (7)	−0.0088 (7)	−0.0058 (7)

S1A—C8A	1.6764 (16)	C3A—C4A	1.387 (2)
O1A—N1A	1.221 (2)	C4A—C5A	1.396 (2)
O2A—N1A	1.219 (2)	C4A—H4AA	0.9500
O3A—N2A	1.227 (2)	C5A—C6A	1.396 (2)
O4A—N2A	1.2230 (19)	C5A—C7A	1.505 (2)
O5A—C7A	1.213 (2)	C6A—H6AA	0.9500
O1B—N1B	1.221 (2)	C9A—H9AA	0.9800
O2B—N1B	1.220 (2)	C9A—H9AB	0.9800
O3B—N2B	1.217 (2)	C9A—H9AC	0.9800
O4B—N2B	1.216 (2)	C10A—H10A	0.9800
O5B—C7B	1.242 (2)	C10A—H10B	0.9800
N1A—C1A	1.477 (2)	C10A—H10C	0.9800
N2A—C3A	1.475 (2)	C1B—C2B	1.382 (2)
N3A—C7A	1.383 (2)	C1B—C6B	1.389 (2)
N3A—C8A	1.404 (2)	C2B—C3B	1.379 (2)
N3A—H1NA	0.84 (2)	C2B—H2BA	0.9500
N4A—C8A	1.324 (2)	C3B—C4B	1.389 (2)
N4A—C9A	1.462 (2)	C4B—C5B	1.394 (2)
N4A—C10A	1.465 (2)	C4B—H4BA	0.9500
N1B—C1B	1.474 (2)	C5B—C6B	1.391 (2)
N2B—C3B	1.476 (2)	C5B—C7B	1.509 (2)
N3B—C7B	1.337 (2)	C6B—H6BA	0.9500
N3B—C8B	1.455 (2)	C8B—H8BA	0.9800
N3B—C9B	1.468 (2)	C8B—H8BB	0.9800
C1A—C2A	1.379 (2)	C8B—H8BC	0.9800
C1A—C6A	1.383 (2)	C9B—H9BA	0.9800
C2A—C3A	1.378 (2)	C9B—H9BB	0.9800
C2A—H2AA	0.9500	C9B—H9BC	0.9800
O2A—N1A—O1A	125.14 (15)	N4A—C9A—H9AA	109.5
O2A—N1A—C1A	117.76 (14)	N4A—C9A—H9AB	109.5
O1A—N1A—C1A	117.09 (14)	H9AA—C9A—H9AB	109.5
O4A—N2A—O3A	124.45 (15)	N4A—C9A—H9AC	109.5
O4A—N2A—C3A	118.26 (14)	H9AA—C9A—H9AC	109.5
O3A—N2A—C3A	117.29 (14)	H9AB—C9A—H9AC	109.5
C7A—N3A—C8A	125.83 (14)	N4A—C10A—H10A	109.5
C7A—N3A—H1NA	114.8 (13)	N4A—C10A—H10B	109.5
C8A—N3A—H1NA	112.8 (13)	H10A—C10A—H10B	109.5
C8A—N4A—C9A	120.93 (14)	N4A—C10A—H10C	109.5
C8A—N4A—C10A	124.44 (14)	H10A—C10A—H10C	109.5
C9A—N4A—C10A	114.36 (14)	H10B—C10A—H10C	109.5
O2B—N1B—O1B	123.94 (15)	C2B—C1B—C6B	123.74 (15)
O2B—N1B—C1B	117.94 (14)	C2B—C1B—N1B	117.83 (14)
O1B—N1B—C1B	118.12 (15)	C6B—C1B—N1B	118.40 (14)
O4B—N2B—O3B	124.34 (15)	C3B—C2B—C1B	115.83 (15)
O4B—N2B—C3B	117.45 (15)	C3B—C2B—H2BA	122.1
O3B—N2B—C3B	118.21 (14)	C1B—C2B—H2BA	122.1
C7B—N3B—C8B	119.81 (15)	C2B—C3B—C4B	123.37 (15)
C7B—N3B—C9B	124.36 (14)	C2B—C3B—N2B	118.42 (14)
C8B—N3B—C9B	115.22 (14)	C4B—C3B—N2B	118.19 (14)
C2A—C1A—C6A	123.23 (15)	C3B—C4B—C5B	118.68 (15)
C2A—C1A—N1A	117.38 (14)	C3B—C4B—H4BA	120.7
C6A—C1A—N1A	119.38 (15)	C5B—C4B—H4BA	120.7
C3A—C2A—C1A	116.55 (15)	C6B—C5B—C4B	120.01 (15)
C3A—C2A—H2AA	121.7	C6B—C5B—C7B	119.19 (14)
C1A—C2A—H2AA	121.7	C4B—C5B—C7B	120.73 (14)
C2A—C3A—C4A	123.43 (15)	C1B—C6B—C5B	118.31 (15)
C2A—C3A—N2A	117.94 (14)	C1B—C6B—H6BA	120.8
C4A—C3A—N2A	118.63 (14)	C5B—C6B—H6BA	120.8
C3A—C4A—C5A	117.88 (15)	O5B—C7B—N3B	123.42 (15)
C3A—C4A—H4AA	121.1	O5B—C7B—C5B	118.99 (14)
C5A—C4A—H4AA	121.1	N3B—C7B—C5B	117.54 (14)
C4A—C5A—C6A	120.56 (14)	N3B—C8B—H8BA	109.5
C4A—C5A—C7A	120.30 (14)	N3B—C8B—H8BB	109.5
C6A—C5A—C7A	119.12 (14)	H8BA—C8B—H8BB	109.5
C1A—C6A—C5A	118.24 (15)	N3B—C8B—H8BC	109.5
C1A—C6A—H6AA	120.9	H8BA—C8B—H8BC	109.5
C5A—C6A—H6AA	120.9	H8BB—C8B—H8BC	109.5
O5A—C7A—N3A	125.54 (15)	N3B—C9B—H9BA	109.5
O5A—C7A—C5A	122.24 (14)	N3B—C9B—H9BB	109.5
N3A—C7A—C5A	112.22 (13)	H9BA—C9B—H9BB	109.5
N4A—C8A—N3A	117.18 (14)	N3B—C9B—H9BC	109.5
N4A—C8A—S1A	124.68 (12)	H9BA—C9B—H9BC	109.5
N3A—C8A—S1A	118.07 (12)	H9BB—C9B—H9BC	109.5
O2A—N1A—C1A—C2A	−14.8 (2)	C7A—N3A—C8A—N4A	50.1 (2)
O1A—N1A—C1A—C2A	164.50 (16)	C7A—N3A—C8A—S1A	−132.89 (15)
O2A—N1A—C1A—C6A	164.30 (15)	O2B—N1B—C1B—C2B	−5.4 (2)
O1A—N1A—C1A—C6A	−16.4 (2)	O1B—N1B—C1B—C2B	175.00 (16)
C6A—C1A—C2A—C3A	0.0 (2)	O2B—N1B—C1B—C6B	172.73 (15)
N1A—C1A—C2A—C3A	179.05 (14)	O1B—N1B—C1B—C6B	−6.9 (2)
C1A—C2A—C3A—C4A	−2.6 (2)	C6B—C1B—C2B—C3B	1.8 (2)
C1A—C2A—C3A—N2A	178.07 (14)	N1B—C1B—C2B—C3B	179.79 (13)
O4A—N2A—C3A—C2A	−173.97 (15)	C1B—C2B—C3B—C4B	−2.4 (2)
O3A—N2A—C3A—C2A	6.0 (2)	C1B—C2B—C3B—N2B	178.90 (14)
O4A—N2A—C3A—C4A	6.7 (2)	O4B—N2B—C3B—C2B	−164.52 (17)
O3A—N2A—C3A—C4A	−173.32 (16)	O3B—N2B—C3B—C2B	15.0 (2)
C2A—C3A—C4A—C5A	2.1 (2)	O4B—N2B—C3B—C4B	16.7 (2)
N2A—C3A—C4A—C5A	−178.57 (13)	O3B—N2B—C3B—C4B	−163.76 (16)
C3A—C4A—C5A—C6A	1.0 (2)	C2B—C3B—C4B—C5B	0.8 (2)
C3A—C4A—C5A—C7A	179.95 (14)	N2B—C3B—C4B—C5B	179.49 (14)
C2A—C1A—C6A—C5A	2.9 (2)	C3B—C4B—C5B—C6B	1.6 (2)
N1A—C1A—C6A—C5A	−176.12 (14)	C3B—C4B—C5B—C7B	178.49 (14)
C4A—C5A—C6A—C1A	−3.4 (2)	C2B—C1B—C6B—C5B	0.4 (2)
C7A—C5A—C6A—C1A	177.66 (14)	N1B—C1B—C6B—C5B	−177.57 (14)
C8A—N3A—C7A—O5A	1.6 (3)	C4B—C5B—C6B—C1B	−2.1 (2)
C8A—N3A—C7A—C5A	−178.18 (14)	C7B—C5B—C6B—C1B	−179.10 (14)
C4A—C5A—C7A—O5A	−140.51 (17)	C8B—N3B—C7B—O5B	2.3 (3)
C6A—C5A—C7A—O5A	38.5 (2)	C9B—N3B—C7B—O5B	−168.35 (16)
C4A—C5A—C7A—N3A	39.3 (2)	C8B—N3B—C7B—C5B	−175.18 (15)
C6A—C5A—C7A—N3A	−141.73 (15)	C9B—N3B—C7B—C5B	14.2 (2)
C9A—N4A—C8A—N3A	−171.11 (15)	C6B—C5B—C7B—O5B	55.5 (2)
C10A—N4A—C8A—N3A	15.3 (2)	C4B—C5B—C7B—O5B	−121.47 (17)
C9A—N4A—C8A—S1A	12.1 (2)	C6B—C5B—C7B—N3B	−126.92 (16)
C10A—N4A—C8A—S1A	−161.53 (14)	C4B—C5B—C7B—N3B	56.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H1NA···O5B	0.84 (2)	2.07 (2)	2.888 (2)	163 (2)
C2B—H2BA···O1Ai	0.95	2.51	3.390 (2)	155
C4B—H4BA···O3Aii	0.95	2.35	3.163 (2)	143
C6B—H6BA···S1A	0.95	2.76	3.6856 (16)	166
C9A—H9AB···O5Biii	0.98	2.48	3.368 (2)	150
C9B—H9BB···O4Biv	0.98	2.46	3.439 (2)	175
C10A—H10B···O2Av	0.98	2.51	3.334 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H1NA⋯O5B	0.84 (2)	2.07 (2)	2.888 (2)	163 (2)
C2B—H2BA⋯O1A i	0.95	2.51	3.390 (2)	155
C4B—H4BA⋯O3A ii	0.95	2.35	3.163 (2)	143
C6B—H6BA⋯S1A	0.95	2.76	3.6856 (16)	166
C9A—H9AB⋯O5B iii	0.98	2.48	3.368 (2)	150
C9B—H9BB⋯O4B iv	0.98	2.46	3.439 (2)	175
C10A—H10B⋯O2A v	0.98	2.51	3.334 (2)	142

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