N-(2-Chloro-4-nitro-phen-yl)-2-nitro-benzamide.

In the title compound, C(13)H(8)ClN(3)O(5), the dihedral angle between the two aromatic rings is 70.74 (6)°. The nitro groups of the Cl-substituted and benzamide benzene rings are twisted by 2.6 (1) and 31.3 (2)°, respectively. The crystal packing shows inter-molecular C-H⋯O hydrogen bonds that link mol-ecules into sheets stacked along [010].

Related literature

For the biological activities of benzanilides and related compounds, see: Makino et al. (2003 ▶); Ho et al. (2002 ▶); Zhichkin et al. (2007 ▶); Jackson et al. (1994 ▶); Capdeville et al. (2002 ▶); Igawa et al. (1999 ▶). For related structures, see: Di Rienzo et al. (1980 ▶); Batsanov & Lyubchik (2003 ▶).

Experimental

Crystal data

C13H8ClN3O5

M = 321.67

Orthorhombic,

a = 7.8053 (9) Å

b = 13.8621 (17) Å

c = 24.101 (3) Å

V = 2607.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 120 (2) K

0.47 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.863, T max = 0.956

21562 measured reflections

3111 independent reflections

2424 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.107

S = 1.04

3111 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006430/si2073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006430/si2073Isup2.hkl

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

C13H8ClN3O5	F000 = 1312
Mr = 321.67	Dx = 1.639 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 769 reflections
a = 7.8053 (9) Å	θ = 2.9–25.7º
b = 13.8621 (17) Å	µ = 0.32 mm−1
c = 24.101 (3) Å	T = 120 (2) K
V = 2607.7 (5) Å3	Prism, colourless
Z = 8	0.47 × 0.20 × 0.14 mm

Bruker SMART APEX diffractometer	3111 independent reflections
Radiation source: sealed tube	2424 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.053
T = 120(2) K	θmax = 27.9º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.863, Tmax = 0.956	k = −18→16
21562 measured reflections	l = −31→31

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.7975P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3111 reflections	Δρmax = 0.39 e Å−3
199 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl1	1.13944 (6)	0.38512 (3)	0.446787 (18)	0.02271 (13)
O1	0.49413 (17)	0.41462 (11)	0.39481 (5)	0.0317 (3)
O2	0.6129 (2)	0.24007 (10)	0.33719 (6)	0.0374 (4)
O3	0.4575 (2)	0.23191 (11)	0.26277 (7)	0.0428 (4)
O4	0.38629 (18)	0.37084 (12)	0.57016 (6)	0.0388 (4)
O5	0.54709 (19)	0.33143 (11)	0.63925 (5)	0.0345 (4)
N1	0.7841 (2)	0.41233 (11)	0.40825 (6)	0.0221 (3)
H1A	0.8816	0.4222	0.3908	0.027*
N2	0.5594 (2)	0.27328 (11)	0.29309 (7)	0.0269 (4)
N3	0.5267 (2)	0.35472 (11)	0.59071 (6)	0.0229 (3)
C1	0.6395 (2)	0.41795 (13)	0.37682 (7)	0.0208 (4)
C2	0.6749 (2)	0.43395 (13)	0.31581 (7)	0.0191 (4)
C3	0.7458 (2)	0.52025 (13)	0.29780 (7)	0.0226 (4)
H3A	0.7797	0.5675	0.3242	0.027*
C4	0.7676 (3)	0.53806 (14)	0.24147 (7)	0.0253 (4)
H4A	0.8179	0.5969	0.2296	0.030*
C5	0.7163 (3)	0.47032 (14)	0.20255 (7)	0.0254 (4)
H5A	0.7310	0.4831	0.1641	0.030*
C6	0.6437 (2)	0.38416 (14)	0.21950 (7)	0.0237 (4)
H6A	0.6073	0.3376	0.1931	0.028*
C7	0.6253 (2)	0.36732 (13)	0.27579 (7)	0.0200 (4)
C8	0.7961 (2)	0.39263 (12)	0.46521 (7)	0.0190 (4)
C9	0.9581 (2)	0.37737 (12)	0.48863 (7)	0.0196 (4)
C10	0.9792 (2)	0.35510 (13)	0.54414 (7)	0.0216 (4)
H10A	1.0907	0.3443	0.5587	0.026*
C11	0.8378 (2)	0.34852 (13)	0.57846 (7)	0.0211 (4)
H11A	0.8497	0.3338	0.6168	0.025*
C12	0.6785 (2)	0.36410 (12)	0.55510 (7)	0.0192 (4)
C13	0.6534 (2)	0.38633 (12)	0.49987 (7)	0.0194 (4)
H13A	0.5414	0.3971	0.4858	0.023*

	U11	U22	U33	U12	U13	U23
Cl1	0.0156 (2)	0.0279 (2)	0.0246 (2)	0.00115 (17)	0.00315 (15)	0.00015 (17)
O1	0.0189 (7)	0.0559 (10)	0.0203 (6)	0.0026 (7)	0.0019 (5)	0.0048 (6)
O2	0.0461 (10)	0.0290 (8)	0.0371 (8)	−0.0004 (7)	0.0064 (7)	0.0124 (6)
O3	0.0422 (10)	0.0316 (8)	0.0545 (10)	−0.0107 (7)	−0.0013 (8)	−0.0119 (7)
O4	0.0163 (7)	0.0739 (12)	0.0262 (7)	−0.0008 (7)	−0.0005 (6)	0.0062 (7)
O5	0.0305 (8)	0.0551 (10)	0.0178 (6)	0.0020 (7)	0.0025 (5)	0.0071 (6)
N1	0.0153 (8)	0.0339 (9)	0.0172 (7)	0.0003 (7)	0.0018 (6)	0.0034 (6)
N2	0.0255 (9)	0.0226 (8)	0.0325 (9)	0.0008 (7)	0.0081 (7)	−0.0029 (7)
N3	0.0203 (8)	0.0300 (9)	0.0182 (7)	−0.0007 (7)	0.0008 (6)	−0.0010 (6)
C1	0.0205 (9)	0.0234 (9)	0.0186 (8)	0.0022 (7)	0.0016 (7)	0.0004 (7)
C2	0.0138 (9)	0.0243 (9)	0.0191 (8)	0.0035 (7)	0.0011 (6)	0.0020 (7)
C3	0.0195 (10)	0.0239 (9)	0.0245 (9)	0.0002 (8)	0.0013 (7)	−0.0004 (7)
C4	0.0238 (10)	0.0243 (9)	0.0278 (9)	0.0030 (8)	0.0062 (8)	0.0069 (8)
C5	0.0252 (10)	0.0331 (11)	0.0178 (8)	0.0079 (8)	0.0043 (7)	0.0052 (8)
C6	0.0237 (10)	0.0276 (10)	0.0197 (8)	0.0048 (8)	−0.0005 (7)	−0.0048 (7)
C7	0.0162 (9)	0.0212 (9)	0.0226 (9)	0.0026 (7)	0.0028 (7)	0.0002 (7)
C8	0.0182 (9)	0.0197 (9)	0.0191 (8)	0.0001 (7)	−0.0012 (7)	0.0003 (7)
C9	0.0162 (9)	0.0172 (9)	0.0254 (9)	0.0003 (7)	0.0029 (7)	−0.0016 (7)
C10	0.0164 (9)	0.0249 (10)	0.0236 (9)	0.0019 (7)	−0.0038 (7)	0.0003 (7)
C11	0.0217 (9)	0.0230 (9)	0.0187 (8)	0.0008 (8)	−0.0030 (7)	0.0015 (7)
C12	0.0196 (9)	0.0186 (8)	0.0192 (8)	−0.0008 (7)	0.0018 (7)	−0.0015 (7)
C13	0.0153 (9)	0.0238 (9)	0.0191 (8)	−0.0009 (7)	−0.0012 (6)	−0.0010 (7)

Cl1—C9	1.7411 (18)	C4—C5	1.386 (3)
O1—C1	1.216 (2)	C4—H4A	0.9500
O2—N2	1.231 (2)	C5—C6	1.383 (3)
O3—N2	1.223 (2)	C5—H5A	0.9500
O4—N3	1.223 (2)	C6—C7	1.384 (2)
O5—N3	1.2240 (19)	C6—H6A	0.9500
N1—C1	1.362 (2)	C8—C13	1.395 (2)
N1—C8	1.403 (2)	C8—C9	1.401 (2)
N1—H1A	0.8800	C9—C10	1.383 (2)
N2—C7	1.462 (2)	C10—C11	1.383 (3)
N3—C12	1.469 (2)	C10—H10A	0.9500
C1—C2	1.512 (2)	C11—C12	1.381 (3)
C2—C3	1.388 (3)	C11—H11A	0.9500
C2—C7	1.391 (3)	C12—C13	1.380 (2)
C3—C4	1.390 (2)	C13—H13A	0.9500
C3—H3A	0.9500
C1—N1—C8	127.64 (15)	C5—C6—C7	118.53 (17)
C1—N1—H1A	116.2	C5—C6—H6A	120.7
C8—N1—H1A	116.2	C7—C6—H6A	120.7
O3—N2—O2	124.13 (17)	C6—C7—C2	122.60 (17)
O3—N2—C7	118.45 (16)	C6—C7—N2	117.81 (16)
O2—N2—C7	117.41 (16)	C2—C7—N2	119.51 (16)
O4—N3—O5	123.50 (16)	C13—C8—C9	118.04 (16)
O4—N3—C12	118.03 (14)	C13—C8—N1	123.03 (16)
O5—N3—C12	118.46 (15)	C9—C8—N1	118.92 (16)
O1—C1—N1	124.98 (16)	C10—C9—C8	122.07 (16)
O1—C1—C2	121.51 (16)	C10—C9—Cl1	118.51 (14)
N1—C1—C2	113.45 (15)	C8—C9—Cl1	119.41 (13)
C3—C2—C7	117.83 (16)	C11—C10—C9	119.91 (17)
C3—C2—C1	120.22 (16)	C11—C10—H10A	120.0
C7—C2—C1	121.73 (16)	C9—C10—H10A	120.0
C2—C3—C4	120.48 (17)	C12—C11—C10	117.65 (16)
C2—C3—H3A	119.8	C12—C11—H11A	121.2
C4—C3—H3A	119.8	C10—C11—H11A	121.2
C5—C4—C3	120.34 (17)	C13—C12—C11	123.77 (17)
C5—C4—H4A	119.8	C13—C12—N3	117.93 (16)
C3—C4—H4A	119.8	C11—C12—N3	118.28 (15)
C6—C5—C4	120.21 (16)	C12—C13—C8	118.55 (17)
C6—C5—H5A	119.9	C12—C13—H13A	120.7
C4—C5—H5A	119.9	C8—C13—H13A	120.7
C8—N1—C1—O1	6.7 (3)	O2—N2—C7—C2	−29.6 (2)
C8—N1—C1—C2	−176.12 (17)	C1—N1—C8—C13	−7.6 (3)
O1—C1—C2—C3	110.1 (2)	C1—N1—C8—C9	171.65 (18)
N1—C1—C2—C3	−67.2 (2)	C13—C8—C9—C10	1.0 (3)
O1—C1—C2—C7	−64.4 (3)	N1—C8—C9—C10	−178.25 (16)
N1—C1—C2—C7	118.28 (19)	C13—C8—C9—Cl1	−179.73 (13)
C7—C2—C3—C4	−0.8 (3)	N1—C8—C9—Cl1	1.0 (2)
C1—C2—C3—C4	−175.50 (17)	C8—C9—C10—C11	−0.8 (3)
C2—C3—C4—C5	1.0 (3)	Cl1—C9—C10—C11	179.93 (14)
C3—C4—C5—C6	−0.3 (3)	C9—C10—C11—C12	0.5 (3)
C4—C5—C6—C7	−0.5 (3)	C10—C11—C12—C13	−0.4 (3)
C5—C6—C7—C2	0.8 (3)	C10—C11—C12—N3	178.34 (16)
C5—C6—C7—N2	−175.84 (17)	O4—N3—C12—C13	−2.9 (2)
C3—C2—C7—C6	−0.1 (3)	O5—N3—C12—C13	177.27 (17)
C1—C2—C7—C6	174.54 (17)	O4—N3—C12—C11	178.28 (18)
C3—C2—C7—N2	176.43 (16)	O5—N3—C12—C11	−1.6 (3)
C1—C2—C7—N2	−8.9 (3)	C11—C12—C13—C8	0.7 (3)
O3—N2—C7—C6	−31.8 (2)	N3—C12—C13—C8	−178.11 (15)
O2—N2—C7—C6	147.07 (18)	C9—C8—C13—C12	−0.9 (2)
O3—N2—C7—C2	151.52 (17)	N1—C8—C13—C12	178.32 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1	0.95	2.24	2.848 (2)	121
C10—H10A···O4i	0.95	2.35	3.246 (2)	157
C11—H11A···O2ii	0.95	2.55	3.202 (2)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1	0.95	2.24	2.848 (2)	121
C10—H10A⋯O4i	0.95	2.35	3.246 (2)	157
C11—H11A⋯O2ii	0.95	2.55	3.202 (2)	126

Symmetry codes: (i) ; (ii) .