Crystal structure of 3-chloro-N-(2-nitro-phen-yl)benzamide.

In the title compound, C13H9ClN2O3, the mean plane of the central amide fragment (r.m.s. deviation = 0.016 Å) subtends dihedral angles of 15.2 (2) and 8.2 (2)° with the chloro- and nitro-substituted benzene rings, respectively. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming C(7) chains which propagate along [010], but no Cl⋯Cl short contacts are observed.

Related literature

For halogen–halogen inter­actions in benzanilide compounds, see: Vener et al. (2013 ▸); Nayak et al. (2011 ▸).

Experimental

Crystal data

C13H9ClN2O3

M = 276.67

Monoclinic,

a = 12.6300 (9) Å

b = 14.1462 (12) Å

c = 6.7797 (6) Å

β = 105.475 (7)°

V = 1167.39 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 123 K

0.40 × 0.08 × 0.05 mm

Data collection

Oxford Diffraction Gemini S diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▸) T min = 0.839, T max = 1.000

10366 measured reflections

10366 independent reflections

7015 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.179

S = 1.00

10367 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.78 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2006 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015014620/hb7476sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014620/hb7476Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014620/hb7476Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014620/hb7476fig1.tif

The mol­ecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Click here for additional data file.

x y z . DOI: 10.1107/S2056989015014620/hb7476fig2.tif

Part of the crystal structure of (I), showing the formation of C(7) chains along [010] [Symmetry code: (i) −x + 1, y − , −z + ].

CCDC reference: 1416793

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H9ClN2O3	Dx = 1.574 Mg m−3
Mr = 276.67	Melting point: 399(1) K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.6300 (9) Å	Cell parameters from 10366 reflections
b = 14.1462 (12) Å	θ = 3.3–27.0°
c = 6.7797 (6) Å	µ = 0.33 mm−1
β = 105.475 (7)°	T = 123 K
V = 1167.39 (17) Å3	Needle, yellow
Z = 4	0.40 × 0.08 × 0.05 mm
F(000) = 568

Oxford Diffraction Gemini S diffractometer	10366 independent reflections
Radiation source: fine-focus sealed tube	7015 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
ω scans	θmax = 29.0°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −17→17
Tmin = 0.839, Tmax = 1.000	k = −17→17
10366 measured reflections	l = −9→8

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0657P)2] where P = (Fo2 + 2Fc2)/3
10367 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Experimental. IR spectra was recorded on a FT—IR SHIMADZU IR-Affinity-1 spectrophotometer. IR (KBr), cm-1, 3348 (amide N–H); 1684 (amide, C=O); 1499 and 1342 (-NO2)Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET) (compiled Nov 25 2010,17:55:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	−0.13525 (11)	0.17880 (10)	0.1877 (3)	0.0345 (4)
O1	0.3249 (3)	0.3758 (3)	0.5550 (7)	0.0413 (11)
O2	0.2403 (3)	0.0390 (3)	0.4902 (6)	0.0417 (12)
O3	0.3446 (4)	−0.0604 (3)	0.6933 (7)	0.0467 (13)
N1	0.2996 (4)	0.2164 (3)	0.5084 (7)	0.0270 (11)
N2	0.3297 (4)	0.0170 (4)	0.6117 (7)	0.0306 (12)
C3	−0.0406 (4)	0.2702 (4)	0.2478 (9)	0.0246 (12)
C2	0.0686 (4)	0.2489 (4)	0.3410 (8)	0.0266 (14)
H2	0.0914	0.1852	0.3698	0.032*
C1	0.1440 (5)	0.3226 (4)	0.3914 (8)	0.0263 (13)
C6	0.1099 (5)	0.4148 (4)	0.3463 (9)	0.0344 (16)
H6	0.1616	0.4650	0.3786	0.041*
C5	−0.0006 (5)	0.4342 (4)	0.2534 (10)	0.0384 (15)
H5	−0.0242	0.4977	0.2241	0.046*
C4	−0.0754 (5)	0.3611 (4)	0.2040 (10)	0.0337 (14)
H4	−0.1505	0.3739	0.1401	0.040*
C7	0.2650 (5)	0.3091 (4)	0.4934 (8)	0.0264 (13)
C8	0.4049 (5)	0.1813 (4)	0.6035 (8)	0.0250 (13)
C9	0.4207 (4)	0.0857 (4)	0.6545 (8)	0.0262 (13)
C10	0.5238 (5)	0.0478 (4)	0.7497 (8)	0.0313 (14)
H10	0.5320	−0.0174	0.7838	0.038*
C11	0.6131 (5)	0.1073 (5)	0.7928 (9)	0.0346 (15)
H11	0.6841	0.0831	0.8575	0.042*
C12	0.6003 (5)	0.2006 (4)	0.7434 (8)	0.0339 (15)
H12	0.6630	0.2406	0.7739	0.041*
C13	0.4981 (4)	0.2388 (4)	0.6497 (8)	0.0298 (14)
H13	0.4916	0.3041	0.6167	0.036*
H1N	0.253 (6)	0.161 (5)	0.460 (10)	0.07 (3)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0180 (6)	0.0357 (8)	0.0445 (8)	−0.0025 (6)	−0.0009 (8)	−0.0003 (8)
O1	0.023 (2)	0.030 (3)	0.064 (3)	−0.001 (2)	−0.001 (2)	−0.002 (2)
O2	0.021 (2)	0.035 (3)	0.061 (3)	−0.0019 (19)	−0.004 (2)	0.001 (2)
O3	0.034 (3)	0.028 (3)	0.072 (3)	−0.002 (2)	0.003 (2)	0.012 (2)
N1	0.017 (2)	0.028 (3)	0.032 (3)	−0.002 (2)	−0.002 (2)	0.000 (2)
N2	0.017 (3)	0.032 (3)	0.041 (3)	−0.002 (2)	0.006 (2)	−0.001 (2)
C3	0.018 (3)	0.028 (3)	0.028 (3)	−0.001 (2)	0.005 (3)	−0.002 (3)
C2	0.018 (3)	0.030 (3)	0.031 (3)	0.001 (3)	0.004 (2)	0.003 (2)
C1	0.019 (3)	0.031 (4)	0.028 (3)	0.000 (3)	0.005 (2)	0.003 (2)
C6	0.023 (3)	0.028 (4)	0.048 (4)	−0.001 (3)	0.002 (3)	−0.001 (3)
C5	0.024 (3)	0.033 (4)	0.053 (4)	0.007 (2)	0.000 (4)	0.009 (4)
C4	0.022 (3)	0.039 (4)	0.039 (3)	0.007 (3)	0.005 (3)	0.005 (3)
C7	0.022 (3)	0.027 (3)	0.027 (3)	−0.002 (3)	0.001 (2)	0.003 (3)
C8	0.016 (3)	0.031 (4)	0.025 (3)	0.001 (3)	0.001 (2)	0.000 (3)
C9	0.015 (3)	0.029 (3)	0.032 (3)	−0.004 (2)	0.003 (2)	−0.001 (3)
C10	0.023 (3)	0.029 (4)	0.040 (4)	0.001 (3)	0.005 (3)	0.003 (3)
C11	0.018 (3)	0.043 (4)	0.041 (4)	−0.002 (3)	0.003 (3)	−0.002 (3)
C12	0.017 (3)	0.042 (4)	0.040 (4)	−0.004 (3)	0.005 (3)	−0.004 (3)
C13	0.022 (3)	0.028 (3)	0.038 (3)	0.002 (3)	0.005 (3)	0.002 (3)

Cl1—C3	1.735 (5)	C6—H6	0.9500
O1—C7	1.212 (6)	C5—C4	1.381 (7)
O2—N2	1.247 (5)	C5—H5	0.9500
O3—N2	1.219 (6)	C4—H4	0.9500
N1—C7	1.376 (7)	C8—C9	1.396 (7)
N1—C8	1.405 (7)	C8—C13	1.397 (7)
N1—H1N	0.98 (7)	C9—C10	1.397 (8)
N2—C9	1.474 (7)	C10—C11	1.374 (8)
C3—C4	1.365 (7)	C10—H10	0.9500
C3—C2	1.388 (7)	C11—C12	1.360 (8)
C2—C1	1.392 (7)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.387 (7)
C1—C6	1.382 (7)	C12—H12	0.9500
C1—C7	1.513 (8)	C13—H13	0.9500
C6—C5	1.396 (7)
C7—N1—C8	127.8 (5)	C5—C4—H4	120.2
C7—N1—H1N	126 (4)	O1—C7—N1	124.1 (5)
C8—N1—H1N	106 (4)	O1—C7—C1	121.3 (5)
O3—N2—O2	121.9 (5)	N1—C7—C1	114.6 (5)
O3—N2—C9	119.0 (5)	C9—C8—C13	116.8 (5)
O2—N2—C9	119.1 (5)	C9—C8—N1	120.8 (5)
C4—C3—C2	121.8 (5)	C13—C8—N1	122.4 (5)
C4—C3—Cl1	119.3 (4)	C8—C9—C10	122.7 (5)
C2—C3—Cl1	118.9 (4)	C8—C9—N2	122.5 (5)
C3—C2—C1	118.7 (5)	C10—C9—N2	114.8 (5)
C3—C2—H2	120.6	C11—C10—C9	118.3 (6)
C1—C2—H2	120.6	C11—C10—H10	120.9
C6—C1—C2	120.0 (5)	C9—C10—H10	120.9
C6—C1—C7	116.0 (5)	C12—C11—C10	120.3 (6)
C2—C1—C7	124.0 (5)	C12—C11—H11	119.8
C1—C6—C5	120.0 (6)	C10—C11—H11	119.8
C1—C6—H6	120.0	C11—C12—C13	121.7 (6)
C5—C6—H6	120.0	C11—C12—H12	119.2
C4—C5—C6	119.9 (6)	C13—C12—H12	119.2
C4—C5—H5	120.0	C12—C13—C8	120.1 (5)
C6—C5—H5	120.0	C12—C13—H13	119.9
C3—C4—C5	119.5 (5)	C8—C13—H13	119.9
C3—C4—H4	120.2
O2—O2—N2—O3	0.0 (3)	C7—N1—C8—C13	−18.1 (9)
O2—O2—N2—C9	0.0 (6)	C13—C8—C9—C10	0.9 (9)
C4—C3—C2—C1	0.2 (9)	N1—C8—C9—C10	−179.8 (5)
Cl1—C3—C2—C1	−179.1 (4)	C13—C8—C9—N2	−179.1 (5)
C3—C2—C1—C6	−0.8 (8)	N1—C8—C9—N2	0.2 (8)
C3—C2—C1—C7	179.9 (5)	O3—N2—C9—C8	−166.2 (6)
C2—C1—C6—C5	1.1 (9)	O2—N2—C9—C8	15.1 (8)
C7—C1—C6—C5	−179.6 (5)	O2—N2—C9—C8	15.1 (8)
C1—C6—C5—C4	−0.9 (10)	O3—N2—C9—C10	13.8 (7)
C2—C3—C4—C5	0.0 (10)	O2—N2—C9—C10	−164.8 (5)
Cl1—C3—C4—C5	179.3 (5)	O2—N2—C9—C10	−164.8 (5)
C6—C5—C4—C3	0.3 (10)	C8—C9—C10—C11	−0.6 (9)
C8—N1—C7—O1	3.7 (10)	N2—C9—C10—C11	179.4 (5)
C8—N1—C7—C1	−176.5 (5)	C9—C10—C11—C12	0.0 (9)
C6—C1—C7—O1	9.1 (8)	C10—C11—C12—C13	0.2 (9)
C2—C1—C7—O1	−171.5 (6)	C11—C12—C13—C8	0.1 (9)
C6—C1—C7—N1	−170.6 (5)	C9—C8—C13—C12	−0.6 (8)
C2—C1—C7—N1	8.7 (8)	N1—C8—C13—C12	−179.9 (5)
C7—N1—C8—C9	162.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.98 (7)	1.75 (7)	2.612 (6)	144 (6)
C10—H10···O1i	0.95	2.39	3.158 (7)	138

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NO2	0.98(7)	1.75(7)	2.612(6)	144(6)
C10H10O1i	0.95	2.39	3.158(7)	138

Symmetry code: (i) .