A co-crystal of 3-(3,5-dinitro­benzo­yl)-1,1-dimethyl­thio­urea and N,N-dimethyl-3,5-dinitro­benzamide

Saeed, S.; Rashid, N.; Butcher, R.J.; Öztürk Yildirim, S.; Hussain, R.

doi:10.1107/S1600536812041864

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3108

doi:10.1107/S1600536812041864

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A co-crystal of 3-(3,5-dinitrobenzoyl)-1,1-dimethylthiourea and N,N-dimethyl-3,5-dinitrobenzamide

Sohail Saeed,^a ^* Naghmana Rashid,^a Ray J. Butcher,^b Sema Öztürk Yildirim ^c and Rizwan Hussain ^d

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, ^bChemistry Department, Howard University, Washington, DC 20059, USA, ^cChemistry Department, Howard University, Washington, DC 20059, USA, and, Department of Physics, Faculty of Sciences, Erciyes University, 38039, Kayseri, Turkey, and ^dNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 2 October 2012; accepted 6 October 2012; online 13 October 2012)

In the title compound, C₁₀H₁₀N₄O₅S·C₉H₉N₃O₅, the amide groups of 3-(3,5-dinitro-benzoyl)-1,1-dimethyl-thiourea and N,N-dimethyl-3,5-dinitro-benzamide molecules are oriented at dihedral angles of 39.13 (8) and 55.97 (11)°, respectively, to the attached benzene rings. In the crystal, the two molecules are linked by an N—H⋯O hydrogen bond. Weak C—H⋯O link the molecules into a sheet parallel to the bc plane. C—H⋯S interactions also occur.

Related literature

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

Experimental

Crystal data

C₁₀H₁₀N₄O₅S·C₉H₉N₃O₅
M_r = 537.47
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.113
S = 1.07
4597 reflections
342 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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⋯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⋯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) -x+1, -y+1, -z; (ii) -x+2, -y+2, -z; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+2, -z; (v) -x+2, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812041864/xu5627sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812041864/xu5627Isup3.cml

checkCIF report

Comment top

The crystal structure of the 1:1 adduct of 3-(3,5-dinitro-benzoyl)-1,1-dimethyl-thiourea and N,N-dimethyl-3,5-dinitro-benzamide is reported. It is related to our previous studies on the structural chemistry of heterocyclic compounds containing an N-substituted thiourea (Saeed et al., 2010a, 2010b, 2011) and amide (Saeed et al., 2012). Herein, as a continuation of these studies, the structure of the title compound, (I), is described.

In the crystal structure of the title compound (Fig. 1), C₁₀H₁₀N₄O₅S, C₉H₉N₃O₅, there are independent different molecules 3-(3,5-dinitro-benzoyl)-1,1-dimethyl-thiourea(A) and N, N-dimethyl-3,5-dinitro-benzamide(B) in the asymmetric unit. Both of the molecule the dinitro-benzene ring systems are planar, with a maximum deviation of 0.295 (1) Å for the O1A atom and 0.286 (2) Å for the O4B atom. In the molecular conformation of 3-(3,5-dinitro-benzoyl)-1,1-dimethyl-thiourea's the C7A=O5A and C8A=S1A bonds are anti to each other. The dihedral angle between the dinitro-benzene unit (C1A—C6A/N1A/N2A/O1A—O4A atoms) and thiourea group (N3A/C8A/N4A/S1A atoms) is 88.2 (1)°. In N-dimethyl-3,5-dinitro-benzamide, the dimethyl amide group is rotated by 59.8 (0.1)° out of the plane of the benzene ring.

The 3-(3,5-dinitro-benzoyl)-1,1-dimethyl-thiourea and N,N-dimethyl-3,5-dinitro-benzamide molecular structure is stabilized by intra- and inter molecular N—H···O and C—H···O hydrogen bonds (Fig. 1 and Table 1). The intermolecular C—H···O hydrogen bonds link the molecules into a sheet parallel to the bc plane (Fig. 2).

Related literature top

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

Experimental top

To a 250 ml round flask fitted with a condenser was added dimethyl amine (0.01 mol), dichloromethane (15 ml) and triethylamine(0.5 ml) with magnetic stirring. 3,5-Dinitrobenzoyl chloride (0.01 mol) was added gradually. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 1.5 h. The product precipitated as a colorless powder, which was washed three times with water and dichloromethane. Recrystallization from ethanol produced the crystals of the title compound.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids. Intramolecular N—H···O hydrogen bond is indicated by a dashed line.
	Fig. 2. Part of the packing diagram of the title compound, showing a molecular sheet formed by intermolecular N—H···O and C—H···O hydrogen bonds (dashed lines).

3-(3,5-Dinitrobenzoyl)-1,1-dimethylthiourea–N,N-dimethyl- 3,5-dinitrobenzamide (1/1) top

Crystal data top

C₁₀H₁₀N₄O₅S·C₉H₉N₃O₅	Z = 2
M_r = 537.47	F(000) = 556
Triclinic, P1	D_x = 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

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	4597 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4099 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.5081 pixels mm^-1	θ_max = 75.7°, θ_min = 3.8°
ω scans	h = −8→12
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011)	k = −11→12
T_min = 0.488, T_max = 0.628	l = −15→15
7591 measured reflections

Refinement top

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(F_o²) + (0.0651P)² + 0.2475P] where P = (F_o² + 2F_c²)/3
4597 reflections	(Δ/σ)_max = 0.001
342 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₀H₁₀N₄O₅S·C₉H₉N₃O₅	γ = 89.129 (4)°
M_r = 537.47	V = 1150.35 (10) Å³
Triclinic, P1	Z = 2
a = 9.8457 (5) Å	Cu Kα radiation
b = 10.0057 (5) Å	µ = 1.90 mm⁻¹
c = 12.5185 (6) Å	T = 123 K
α = 72.413 (5)°	0.44 × 0.38 × 0.27 mm
β = 78.428 (4)°

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	4597 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011)	4099 reflections with I > 2σ(I)
T_min = 0.488, T_max = 0.628	R_int = 0.025
7591 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.44 e Å⁻³
4597 reflections	Δρ_min = −0.33 e Å⁻³
342 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···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) −x+1, −y+1, −z; (ii) −x+2, −y+2, −z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+2, −z; (v) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₄O₅S·C₉H₉N₃O₅
M_r	537.47
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	9.8457 (5), 10.0057 (5), 12.5185 (6)
α, β, γ (°)	72.413 (5), 78.428 (4), 89.129 (4)
V (Å³)	1150.35 (10)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.44 × 0.38 × 0.27

Data collection
Diffractometer	Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Agilent, 2011)
T_min, T_max	0.488, 0.628
No. of measured, independent and observed [I > 2σ(I)] reflections	7591, 4597, 4099
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.113, 1.07
No. of reflections	4597
No. of parameters	342
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.33

Computer programs: CrysAlis PRO (Agilent, 2011), CrysAlis RED (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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···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) −x+1, −y+1, −z; (ii) −x+2, −y+2, −z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+2, −z; (v) −x+2, −y+1, −z.

Acknowledgements

RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England. Google Scholar
Saeed, S., Rashid, N., Butcher, R. J., Öztürk Yildirim, S. & Hussain, R. (2012). Acta Cryst. E68, o2762. CSD CrossRef IUCr Journals Google Scholar
Saeed, S., Rashid, N., Hussain, R., Jones, P. G. & Bhatti, M. H. (2010a). Cent. Eur. J. Chem. 8, 550–558. Web of Science CSD CrossRef CAS Google Scholar
Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010b). Eur. J. Med. Chem. 45, 1323–1331. Web of Science CSD CrossRef CAS PubMed Google Scholar
Saeed, S., Rashid, N., Jones, P. G. & Tahir, A. (2011). J. Heterocycl. Chem. 48, 74–84. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3108

doi:10.1107/S1600536812041864

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A co-crystal of 3-(3,5-di­nitro­benzo­yl)-1,1-di­methyl­thio­urea and N,N-di­methyl-3,5-di­nitro­benzamide

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Acknowledgements

References

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A co-crystal of 3-(3,5-dinitrobenzoyl)-1,1-dimethylthiourea and N,N-dimethyl-3,5-dinitrobenzamide