2-Amino-5-nitro-phenyl 2-chloro-phenyl ketone.

In the title compound, C(13)H(9)ClN(2)O(3), an intra-molecular hydrogen bond between the carbonyl O and an amine H atom from the 2-amino-benzoyl group stabilizes the mol-ecule, keeping these two groups nearly in the same plane [dihedral angle 14.6 (6)°]. The dihedral angle between the mean planes of the planar 2-amino-benzoyl and 2-chloro-benzoyl groups is 73.8 (6)°. The crystal packing is stabilized by a collection of inter-mediate hydrogen-bonding inter-actions which forms an infinite N-H⋯O⋯H-N-H⋯O hydrogen-bonded chain along the c axis in concert with weak N-H⋯Cl inter-actions in the same direction, producing a two-dimensional inter-molecular bonding network parallel to (001). Additional weak C-Cl⋯Cg [Cl⋯Cg = 3.858 (3) Å] and N-O⋯Cg [O⋯Cg = 3.574 (1) and 3.868 (6) Å] π-ring inter-actions provide added support to the crystal stability. A MOPAC computational calculation gives support to these observations.

Related literature

For related structures, see: Cox et al. (1997 ▶, 2008 ▶); Harrison et al. (2005 ▶); Malathy Sony et al. (2005 ▶); Prasanna & Guru Row (2000 ▶); Xing et al. (2005 ▶). For background to benzophenone derivatives, see: Colpaert et al. (2004 ▶); Deleu et al. (1992 ▶); Duncan et al. (2004 ▶); Evans et al. (1987 ▶); Ottosen et al. (2003 ▶); Revesz et al. (2004 ▶); Sieroń et al. (2004 ▶); Wiesner et al. (2002 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For MOPAC n class="Species">AM1 computational calculations, see: Schmidt & Polik (2007 ▶).

Experimental

Crystal data

C13H9ClN2O3

M = 276.67

Monoclinic,

a = 10.6120 (3) Å

b = 11.3314 (3) Å

c = 10.8456 (3) Å

β = 108.399 (3)°

V = 1237.50 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 110 K

0.47 × 0.36 × 0.28 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.868, T max = 0.916

8758 measured reflections

4131 independent reflections

3069 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.04

4131 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; 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 global, I. DOI: 10.1107/S160053680902755X/kj2123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902755X/kj2123Isup2.hkl

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

C13H9ClN2O3	F(000) = 568
Mr = 276.67	Dx = 1.485 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4505 reflections
a = 10.6120 (3) Å	θ = 4.7–32.6°
b = 11.3314 (3) Å	µ = 0.31 mm−1
c = 10.8456 (3) Å	T = 110 K
β = 108.399 (3)°	Chunk, colorless
V = 1237.50 (6) Å3	0.47 × 0.36 × 0.28 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	4131 independent reflections
Radiation source: fine-focus sealed tube	3069 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 10.5081 pixels mm-1	θmax = 32.7°, θmin = 4.7°
φ and ω scans	h = −15→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −13→16
Tmin = 0.868, Tmax = 0.916	l = −16→11
8758 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0548P)2] where P = (Fo2 + 2Fc2)/3
4131 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.27 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
Cl	0.96431 (3)	0.63182 (3)	0.78827 (3)	0.02769 (10)
O1	0.48712 (10)	0.77733 (9)	0.32532 (9)	0.0350 (2)
O2	0.50201 (9)	0.76958 (8)	0.52898 (8)	0.0271 (2)
O3	0.82129 (9)	0.31290 (8)	0.73196 (7)	0.02303 (19)
N1	0.82197 (10)	0.31577 (9)	0.48161 (9)	0.0214 (2)
H1A	0.8367	0.2872	0.4120	0.026*
H1B	0.8515	0.2779	0.5561	0.026*
N2	0.52756 (10)	0.73094 (9)	0.43331 (9)	0.0211 (2)
C1	0.75466 (11)	0.41681 (10)	0.47433 (10)	0.0162 (2)
C2	0.70760 (12)	0.47688 (11)	0.35352 (10)	0.0197 (2)
H2A	0.7267	0.4453	0.2802	0.024*
C3	0.63591 (12)	0.57843 (11)	0.33976 (10)	0.0202 (2)
H3A	0.6049	0.6169	0.2579	0.024*
C4	0.60840 (11)	0.62550 (10)	0.44837 (10)	0.0169 (2)
C5	0.65568 (10)	0.57301 (10)	0.56856 (10)	0.0157 (2)
H5A	0.6376	0.6076	0.6410	0.019*
C6	0.73013 (10)	0.46916 (10)	0.58484 (10)	0.0148 (2)
C7	0.77971 (11)	0.41506 (10)	0.71401 (10)	0.0159 (2)
C8	0.77845 (11)	0.48654 (10)	0.83067 (9)	0.0154 (2)
C9	0.85984 (11)	0.58380 (11)	0.87385 (10)	0.0184 (2)
C10	0.86275 (12)	0.64296 (11)	0.98728 (11)	0.0228 (3)
H10A	0.9199	0.7088	1.0165	0.027*
C11	0.78122 (12)	0.60456 (12)	1.05687 (11)	0.0240 (3)
H11A	0.7827	0.6443	1.1345	0.029*
C12	0.69750 (12)	0.50870 (12)	1.01432 (10)	0.0214 (2)
H12A	0.6406	0.4839	1.0616	0.026*
C13	0.69720 (11)	0.44907 (10)	0.90242 (10)	0.0174 (2)
H13A	0.6413	0.3823	0.8744	0.021*

	U11	U22	U33	U12	U13	U23
Cl	0.02888 (16)	0.03213 (19)	0.02478 (15)	−0.01301 (13)	0.01233 (12)	−0.00264 (12)
O1	0.0449 (6)	0.0315 (6)	0.0230 (4)	0.0161 (5)	0.0026 (4)	0.0071 (4)
O2	0.0329 (5)	0.0238 (5)	0.0292 (4)	0.0088 (4)	0.0161 (4)	0.0015 (4)
O3	0.0372 (5)	0.0166 (4)	0.0187 (4)	0.0056 (4)	0.0137 (3)	0.0035 (3)
N1	0.0332 (5)	0.0174 (5)	0.0147 (4)	0.0061 (4)	0.0092 (4)	−0.0015 (4)
N2	0.0217 (5)	0.0192 (5)	0.0209 (5)	0.0027 (4)	0.0045 (4)	0.0014 (4)
C1	0.0192 (5)	0.0147 (5)	0.0147 (5)	−0.0015 (4)	0.0054 (4)	−0.0022 (4)
C2	0.0259 (6)	0.0212 (6)	0.0125 (4)	0.0014 (5)	0.0066 (4)	−0.0012 (4)
C3	0.0242 (5)	0.0220 (6)	0.0129 (5)	0.0015 (5)	0.0035 (4)	0.0013 (4)
C4	0.0180 (5)	0.0151 (6)	0.0172 (5)	0.0010 (4)	0.0047 (4)	−0.0006 (4)
C5	0.0179 (5)	0.0151 (6)	0.0149 (5)	−0.0023 (4)	0.0063 (4)	−0.0030 (4)
C6	0.0182 (5)	0.0139 (5)	0.0125 (4)	−0.0011 (4)	0.0052 (4)	−0.0006 (4)
C7	0.0194 (5)	0.0150 (5)	0.0148 (5)	−0.0009 (4)	0.0076 (4)	0.0005 (4)
C8	0.0201 (5)	0.0147 (5)	0.0115 (4)	0.0026 (4)	0.0051 (4)	0.0019 (4)
C9	0.0200 (5)	0.0193 (6)	0.0165 (5)	−0.0007 (4)	0.0066 (4)	0.0009 (4)
C10	0.0257 (6)	0.0220 (6)	0.0191 (5)	−0.0029 (5)	0.0047 (4)	−0.0050 (5)
C11	0.0290 (6)	0.0271 (7)	0.0155 (5)	0.0027 (5)	0.0067 (4)	−0.0047 (5)
C12	0.0247 (6)	0.0267 (7)	0.0149 (5)	0.0023 (5)	0.0091 (4)	0.0018 (4)
C13	0.0211 (5)	0.0163 (6)	0.0150 (5)	−0.0004 (4)	0.0060 (4)	0.0016 (4)

Cl—C9	1.7426 (12)	C5—C6	1.3972 (15)
O1—N2	1.2309 (13)	C5—H5A	0.9500
O2—N2	1.2326 (13)	C6—C7	1.4663 (15)
O3—C7	1.2322 (14)	C7—C8	1.5059 (15)
N1—C1	1.3385 (15)	C8—C9	1.3873 (16)
N1—H1A	0.8800	C8—C13	1.3975 (15)
N1—H1B	0.8800	C9—C10	1.3927 (16)
N2—C4	1.4498 (15)	C10—C11	1.3856 (18)
C1—C2	1.4201 (15)	C10—H10A	0.9500
C1—C6	1.4329 (14)	C11—C12	1.3868 (18)
C2—C3	1.3614 (17)	C11—H11A	0.9500
C2—H2A	0.9500	C12—C13	1.3882 (15)
C3—C4	1.4052 (15)	C12—H12A	0.9500
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.3754 (15)
C1—N1—H1A	120.0	C1—C6—C7	121.40 (10)
C1—N1—H1B	120.0	O3—C7—C6	123.11 (10)
H1A—N1—H1B	120.0	O3—C7—C8	118.06 (9)
O1—N2—O2	123.10 (11)	C6—C7—C8	118.83 (10)
O1—N2—C4	118.38 (10)	C9—C8—C13	118.76 (10)
O2—N2—C4	118.52 (9)	C9—C8—C7	122.77 (9)
N1—C1—C2	119.35 (10)	C13—C8—C7	118.36 (10)
N1—C1—C6	122.63 (10)	C8—C9—C10	121.23 (10)
C2—C1—C6	118.00 (10)	C8—C9—Cl	120.08 (8)
C3—C2—C1	121.87 (10)	C10—C9—Cl	118.67 (9)
C3—C2—H2A	119.1	C11—C10—C9	119.10 (11)
C1—C2—H2A	119.1	C11—C10—H10A	120.5
C2—C3—C4	119.06 (10)	C9—C10—H10A	120.5
C2—C3—H3A	120.5	C10—C11—C12	120.62 (11)
C4—C3—H3A	120.5	C10—C11—H11A	119.7
C5—C4—C3	121.35 (11)	C12—C11—H11A	119.7
C5—C4—N2	119.28 (10)	C11—C12—C13	119.78 (11)
C3—C4—N2	119.37 (10)	C11—C12—H12A	120.1
C4—C5—C6	120.43 (10)	C13—C12—H12A	120.1
C4—C5—H5A	119.8	C12—C13—C8	120.49 (11)
C6—C5—H5A	119.8	C12—C13—H13A	119.8
C5—C6—C1	119.20 (9)	C8—C13—H13A	119.8
C5—C6—C7	119.40 (9)
N1—C1—C2—C3	178.41 (11)	C1—C6—C7—O3	−14.58 (17)
C6—C1—C2—C3	−2.95 (17)	C5—C6—C7—C8	−14.71 (16)
C1—C2—C3—C4	0.38 (18)	C1—C6—C7—C8	166.26 (10)
C2—C3—C4—C5	1.95 (18)	O3—C7—C8—C9	112.56 (13)
C2—C3—C4—N2	−177.50 (11)	C6—C7—C8—C9	−68.24 (14)
O1—N2—C4—C5	179.35 (11)	O3—C7—C8—C13	−63.73 (14)
O2—N2—C4—C5	−1.01 (16)	C6—C7—C8—C13	115.48 (12)
O1—N2—C4—C3	−1.19 (17)	C13—C8—C9—C10	0.79 (17)
O2—N2—C4—C3	178.46 (11)	C7—C8—C9—C10	−175.49 (11)
C3—C4—C5—C6	−1.56 (17)	C13—C8—C9—Cl	179.06 (8)
N2—C4—C5—C6	177.89 (10)	C7—C8—C9—Cl	2.79 (15)
C4—C5—C6—C1	−1.10 (16)	C8—C9—C10—C11	−0.93 (18)
C4—C5—C6—C7	179.85 (10)	Cl—C9—C10—C11	−179.23 (10)
N1—C1—C6—C5	−178.14 (11)	C9—C10—C11—C12	−0.14 (19)
C2—C1—C6—C5	3.28 (16)	C10—C11—C12—C13	1.31 (19)
N1—C1—C6—C7	0.89 (17)	C11—C12—C13—C8	−1.45 (18)
C2—C1—C6—C7	−177.69 (10)	C9—C8—C13—C12	0.41 (17)
C5—C6—C7—O3	164.45 (11)	C7—C8—C13—C12	176.85 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.88	2.22	3.0733 (12)	164
N1—H1B···O3	0.88	2.07	2.7176 (12)	130
N1—H1B···Clii	0.88	2.71	3.4848 (10)	148
C13—H13A···O2iii	0.95	2.46	3.1862 (14)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.88	2.22	3.0733 (12)	164
N1—H1B⋯O3	0.88	2.07	2.7176 (12)	130
N1—H1B⋯Clii	0.88	2.71	3.4848 (10)	148
C13—H13A⋯O2iii	0.95	2.46	3.1862 (14)	133

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