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

The title compound, C(13)H(9)ClN(2)O(3), is almost planar, showing a dihedral angle of 4.63 (6)° between the aromatic ring planes. The nitro group also lies in the plane, the C-C-N-O torsion angle being 6.7 (2)°. There is an intamolecular C-H⋯O hydrogen bond. The crystal structure features N-H⋯O(nitro) hydrogen bonds that link the mol-ecules into zigzag chains extending along [010].

Related literature

For background information on aromatic polyimides, see: Yang et al. (1999 ▶); More et al. (2010 ▶); Litvinov et al., (2010 ▶); Sheng et al. (2009 ▶); Choi et al. (1992 ▶); Hsiao & Lin (2004 ▶); Li et al. (2007 ▶); Liaw et al. (2005 ▶). For related structures, see Saeed et al. (2011 ▶); Wardell et al. (2006 ▶).

Experimental

Crystal data

C13H9ClN2O3

M = 276.67

Monoclinic,

a = 9.6019 (7) Å

b = 13.0688 (10) Å

c = 9.6412 (7) Å

β = 103.853 (1)°

V = 1174.64 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 130 K

0.49 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.855, T max = 0.943

10822 measured reflections

2808 independent reflections

2557 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.08

2808 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036082/bt6822sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036082/bt6822Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036082/bt6822Isup3.cml

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

C13H9ClN2O3	F(000) = 568
Mr = 276.67	Dx = 1.564 Mg m−3
Monoclinic, P21/n	Melting point: 141 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.6019 (7) Å	Cell parameters from 5166 reflections
b = 13.0688 (10) Å	θ = 2.7–28.3°
c = 9.6412 (7) Å	µ = 0.33 mm−1
β = 103.853 (1)°	T = 130 K
V = 1174.64 (15) Å3	Prism, yellow
Z = 4	0.49 × 0.20 × 0.18 mm

Bruker SMART APEX diffractometer	2808 independent reflections
Radiation source: sealed tube	2557 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 27.9°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→12
Tmin = 0.855, Tmax = 0.943	k = −16→17
10822 measured reflections	l = −12→12

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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.116	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.6505P] where P = (Fo2 + 2Fc2)/3
2808 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.76 e Å−3
0 restraints	Δρmin = −0.26 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
Cl1	0.86234 (4)	0.07922 (3)	0.98180 (4)	0.02702 (14)
O1	0.81457 (12)	0.60046 (9)	0.92017 (14)	0.0290 (3)
O2	0.38514 (13)	1.02953 (9)	0.81384 (14)	0.0317 (3)
O3	0.20735 (12)	0.93858 (9)	0.69700 (13)	0.0268 (3)
N1	0.61843 (14)	0.49653 (10)	0.87249 (14)	0.0212 (3)
H1A	0.5241	0.4972	0.8458	0.025*
N2	0.33274 (14)	0.94804 (11)	0.76579 (15)	0.0216 (3)
C1	0.68462 (17)	0.58903 (12)	0.88325 (17)	0.0208 (3)
C2	0.58628 (16)	0.68089 (12)	0.84829 (16)	0.0193 (3)
C3	0.64838 (16)	0.77663 (12)	0.88474 (17)	0.0210 (3)
H3A	0.7479	0.7812	0.9287	0.025*
C4	0.56698 (17)	0.86526 (12)	0.85776 (17)	0.0215 (3)
H4A	0.6090	0.9305	0.8833	0.026*
C5	0.42207 (16)	0.85577 (11)	0.79222 (16)	0.0193 (3)
C6	0.35741 (16)	0.76187 (13)	0.75241 (17)	0.0217 (3)
H6A	0.2584	0.7578	0.7064	0.026*
C7	0.44026 (17)	0.67427 (12)	0.78121 (17)	0.0224 (3)
H7A	0.3977	0.6092	0.7553	0.027*
C8	0.68397 (16)	0.39913 (12)	0.89933 (16)	0.0198 (3)
C9	0.59677 (17)	0.31396 (12)	0.85279 (17)	0.0220 (3)
H9A	0.4996	0.3238	0.8032	0.026*
C10	0.65021 (17)	0.21567 (13)	0.87802 (17)	0.0225 (3)
H10A	0.5907	0.1580	0.8466	0.027*
C11	0.79284 (17)	0.20303 (12)	0.95039 (17)	0.0203 (3)
C12	0.88114 (16)	0.28597 (13)	0.99628 (17)	0.0213 (3)
H12A	0.9784	0.2756	1.0452	0.026*
C13	0.82716 (17)	0.38472 (13)	0.97057 (17)	0.0215 (3)
H13A	0.8875	0.4420	1.0014	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.0277 (2)	0.0195 (2)	0.0341 (2)	0.00400 (14)	0.00786 (16)	0.00411 (15)
O1	0.0156 (5)	0.0224 (6)	0.0469 (7)	−0.0015 (4)	0.0033 (5)	0.0064 (5)
O2	0.0278 (6)	0.0180 (6)	0.0468 (8)	−0.0001 (5)	0.0041 (5)	−0.0024 (5)
O3	0.0182 (5)	0.0259 (6)	0.0344 (6)	0.0029 (4)	0.0029 (5)	−0.0003 (5)
N1	0.0142 (6)	0.0192 (6)	0.0288 (7)	0.0001 (5)	0.0023 (5)	0.0008 (5)
N2	0.0194 (6)	0.0216 (7)	0.0248 (6)	0.0008 (5)	0.0069 (5)	0.0004 (5)
C1	0.0177 (7)	0.0216 (8)	0.0232 (7)	−0.0007 (6)	0.0051 (6)	0.0026 (6)
C2	0.0177 (7)	0.0203 (7)	0.0202 (7)	−0.0005 (5)	0.0053 (5)	0.0019 (5)
C3	0.0153 (6)	0.0227 (8)	0.0238 (7)	−0.0022 (6)	0.0024 (6)	0.0009 (6)
C4	0.0199 (7)	0.0195 (7)	0.0247 (7)	−0.0033 (6)	0.0046 (6)	−0.0005 (6)
C5	0.0183 (7)	0.0195 (7)	0.0208 (7)	0.0021 (6)	0.0063 (5)	0.0006 (5)
C6	0.0146 (6)	0.0243 (8)	0.0248 (8)	−0.0014 (6)	0.0023 (5)	−0.0006 (6)
C7	0.0188 (7)	0.0187 (7)	0.0286 (8)	−0.0029 (6)	0.0033 (6)	−0.0014 (6)
C8	0.0191 (7)	0.0194 (7)	0.0218 (7)	0.0014 (6)	0.0067 (6)	0.0012 (6)
C9	0.0158 (7)	0.0249 (8)	0.0242 (7)	0.0002 (6)	0.0026 (6)	−0.0010 (6)
C10	0.0195 (7)	0.0218 (8)	0.0267 (8)	−0.0037 (6)	0.0063 (6)	−0.0026 (6)
C11	0.0203 (7)	0.0183 (7)	0.0237 (7)	0.0027 (6)	0.0083 (6)	0.0027 (6)
C12	0.0159 (7)	0.0239 (8)	0.0239 (7)	0.0012 (6)	0.0042 (6)	0.0024 (6)
C13	0.0181 (7)	0.0215 (7)	0.0247 (7)	−0.0009 (6)	0.0048 (6)	0.0001 (6)

Cl1—C11	1.7488 (16)	C5—C6	1.387 (2)
O1—C1	1.222 (2)	C6—C7	1.384 (2)
O2—N2	1.2207 (19)	C6—H6A	0.9500
O3—N2	1.2339 (17)	C7—H7A	0.9500
N1—C1	1.358 (2)	C8—C13	1.395 (2)
N1—C8	1.4161 (19)	C8—C9	1.400 (2)
N1—H1A	0.8800	C9—C10	1.383 (2)
N2—C5	1.466 (2)	C9—H9A	0.9500
C1—C2	1.515 (2)	C10—C11	1.390 (2)
C2—C3	1.394 (2)	C10—H10A	0.9500
C2—C7	1.399 (2)	C11—C12	1.382 (2)
C3—C4	1.387 (2)	C12—C13	1.391 (2)
C3—H3A	0.9500	C12—H12A	0.9500
C4—C5	1.389 (2)	C13—H13A	0.9500
C4—H4A	0.9500
C1—N1—C8	127.36 (13)	C5—C6—H6A	120.7
C1—N1—H1A	116.3	C6—C7—C2	120.39 (14)
C8—N1—H1A	116.3	C6—C7—H7A	119.8
O2—N2—O3	123.50 (14)	C2—C7—H7A	119.8
O2—N2—C5	118.73 (13)	C13—C8—C9	119.58 (14)
O3—N2—C5	117.76 (13)	C13—C8—N1	123.64 (14)
O1—C1—N1	123.89 (14)	C9—C8—N1	116.77 (13)
O1—C1—C2	120.44 (14)	C10—C9—C8	120.91 (14)
N1—C1—C2	115.67 (13)	C10—C9—H9A	119.5
C3—C2—C7	119.53 (14)	C8—C9—H9A	119.5
C3—C2—C1	116.68 (13)	C9—C10—C11	118.56 (14)
C7—C2—C1	123.79 (14)	C9—C10—H10A	120.7
C4—C3—C2	120.96 (14)	C11—C10—H10A	120.7
C4—C3—H3A	119.5	C12—C11—C10	121.51 (14)
C2—C3—H3A	119.5	C12—C11—Cl1	119.40 (12)
C3—C4—C5	117.96 (14)	C10—C11—Cl1	119.09 (12)
C3—C4—H4A	121.0	C11—C12—C13	119.80 (14)
C5—C4—H4A	121.0	C11—C12—H12A	120.1
C6—C5—C4	122.55 (14)	C13—C12—H12A	120.1
C6—C5—N2	118.36 (13)	C12—C13—C8	119.63 (14)
C4—C5—N2	119.09 (14)	C12—C13—H13A	120.2
C7—C6—C5	118.60 (14)	C8—C13—H13A	120.2
C7—C6—H6A	120.7
C8—N1—C1—O1	−0.7 (3)	N2—C5—C6—C7	−177.98 (14)
C8—N1—C1—C2	−179.73 (14)	C5—C6—C7—C2	−0.4 (2)
O1—C1—C2—C3	−11.2 (2)	C3—C2—C7—C6	−0.7 (2)
N1—C1—C2—C3	167.93 (14)	C1—C2—C7—C6	−179.81 (15)
O1—C1—C2—C7	167.99 (16)	C1—N1—C8—C13	14.2 (3)
N1—C1—C2—C7	−12.9 (2)	C1—N1—C8—C9	−167.02 (15)
C7—C2—C3—C4	1.2 (2)	C13—C8—C9—C10	0.8 (2)
C1—C2—C3—C4	−179.64 (14)	N1—C8—C9—C10	−178.06 (14)
C2—C3—C4—C5	−0.6 (2)	C8—C9—C10—C11	−0.2 (2)
C3—C4—C5—C6	−0.5 (2)	C9—C10—C11—C12	−0.3 (2)
C3—C4—C5—N2	178.45 (14)	C9—C10—C11—Cl1	−179.48 (12)
O2—N2—C5—C6	172.37 (15)	C10—C11—C12—C13	0.2 (2)
O3—N2—C5—C6	−6.8 (2)	Cl1—C11—C12—C13	179.39 (12)
O2—N2—C5—C4	−6.7 (2)	C11—C12—C13—C8	0.4 (2)
O3—N2—C5—C4	174.13 (14)	C9—C8—C13—C12	−0.9 (2)
C4—C5—C6—C7	1.0 (2)	N1—C8—C13—C12	177.89 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1	0.95	2.26	2.859 (2)	120
N1—H1A···O3i	0.88	2.29	3.1312 (17)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1	0.95	2.26	2.859 (2)	120
N1—H1A⋯O3i	0.88	2.29	3.1312 (17)	159

Symmetry code: (i) .