4-Formyl-2-nitro-phenyl 2-chloro-benzoate.

In the title compound, C14H8ClNO5, the benzene rings form a dihedral angle of 19.55 (9)°. The mean plane of the central ester group [r.m.s. deviation = 0.024 Å] forms dihedral angles of 53.28 (13) and 36.93 (16)°, respectively, with the nitro- and chloro-substituted rings. The nitro group forms a dihedral angle of 19.24 (19)° with the benzene ring to which it is attached. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming C(7) chains, which run along [100].

Related literature

For industrial applications of nitro­aromatic compounds, see: Ju & Parales (2010 ▶). For similar structures, see: Moreno-Fuquen et al. (2013a ▶,b ▶); For information on hydrogen bonds, see: Nardelli (1995 ▶). For hydrogen-bond graph-set motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C14H8ClNO5

M = 305.66

Orthorhombic,

a = 16.2367 (7) Å

b = 7.1047 (2) Å

c = 11.4018 (3) Å

V = 1315.28 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.22 × 0.19 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

4581 measured reflections

2449 independent reflections

1762 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.03

2449 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack parameter determined using 664 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: −0.05 (5)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); 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/S1600536813031346/lh5661sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031346/lh5661Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031346/lh5661Isup3.cml

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

C14H8ClNO5	Dx = 1.544 Mg m−3
Mr = 305.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 4580 reflections
a = 16.2367 (7) Å	θ = 3.1–26.0°
b = 7.1047 (2) Å	µ = 0.31 mm−1
c = 11.4018 (3) Å	T = 293 K
V = 1315.28 (8) Å3	Prism, colourless
Z = 4	0.22 × 0.19 × 0.03 mm
F(000) = 624

Nonius KappaCCD diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 3.1°
CCD rotation images, thick slices scans	h = −20→19
4581 measured reflections	k = −8→8
2449 independent reflections	l = −14→12
1762 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0719P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.20 e Å−3
2449 reflections	Δρmin = −0.19 e Å−3
194 parameters	Absolute structure: Flack parameter determined using 664 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.05 (5)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.22510 (10)	0.32842 (19)	0.13842 (11)	0.0778 (5)
N1	0.3173 (2)	0.2738 (6)	0.7453 (3)	0.0584 (9)
O1	0.2028 (2)	0.1765 (5)	0.3854 (3)	0.0738 (10)
O2	0.27033 (18)	0.3692 (4)	0.5103 (3)	0.0553 (8)
O3	0.3734 (2)	0.3131 (6)	0.6813 (4)	0.0923 (13)
O4	0.3268 (3)	0.1925 (6)	0.8386 (3)	0.0919 (13)
O5	0.0483 (3)	0.3553 (6)	0.9720 (4)	0.0923 (13)
C1	0.3298 (3)	0.3250 (5)	0.3259 (4)	0.0510 (11)
C2	0.4090 (3)	0.3457 (6)	0.3744 (5)	0.0613 (12)
H2	0.4163	0.3370	0.4552	0.074*
C3	0.4757 (3)	0.3789 (7)	0.3028 (6)	0.0732 (14)
H3	0.5280	0.3908	0.3352	0.088*
C4	0.4654 (4)	0.3944 (7)	0.1839 (5)	0.0787 (17)
H4	0.5109	0.4163	0.1362	0.094*
C5	0.3891 (4)	0.3780 (7)	0.1347 (5)	0.0733 (15)
H5	0.3827	0.3907	0.0540	0.088*
C6	0.3205 (3)	0.3422 (6)	0.2056 (4)	0.0587 (12)
C7	0.2598 (3)	0.2788 (7)	0.4038 (4)	0.0534 (11)
C8	0.2101 (3)	0.3581 (6)	0.5953 (4)	0.0474 (10)
C9	0.1291 (3)	0.4003 (7)	0.5704 (4)	0.0556 (11)
H9	0.1135	0.4276	0.4938	0.067*
C10	0.0713 (3)	0.4020 (6)	0.6588 (4)	0.0564 (11)
H10	0.0166	0.4285	0.6411	0.068*
C11	0.0937 (3)	0.3646 (5)	0.7739 (4)	0.0510 (10)
C12	0.1744 (3)	0.3209 (5)	0.7998 (4)	0.0488 (10)
H12	0.1897	0.2937	0.8766	0.059*
C13	0.2326 (3)	0.3176 (5)	0.7108 (4)	0.0452 (10)
C14	0.0319 (4)	0.3748 (8)	0.8689 (6)	0.0731 (14)
H14	−0.029 (4)	0.423 (8)	0.840 (5)	0.098 (18)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0968 (11)	0.0838 (8)	0.0528 (7)	0.0064 (7)	−0.0095 (8)	−0.0049 (6)
N1	0.051 (2)	0.076 (2)	0.048 (2)	0.003 (2)	−0.0027 (18)	−0.0013 (19)
O1	0.079 (2)	0.080 (2)	0.062 (2)	−0.018 (2)	0.0142 (18)	−0.0172 (16)
O2	0.0544 (18)	0.075 (2)	0.0363 (16)	−0.0051 (15)	0.0054 (13)	−0.0026 (14)
O3	0.047 (2)	0.156 (4)	0.074 (3)	−0.006 (2)	0.0005 (18)	0.027 (2)
O4	0.076 (3)	0.142 (4)	0.058 (2)	0.024 (2)	−0.0046 (18)	0.028 (2)
O5	0.093 (3)	0.128 (3)	0.056 (3)	0.002 (2)	0.027 (2)	0.0030 (19)
C1	0.062 (3)	0.050 (2)	0.041 (2)	0.004 (2)	0.007 (2)	−0.0024 (17)
C2	0.065 (3)	0.062 (3)	0.057 (3)	0.000 (2)	0.007 (2)	−0.001 (2)
C3	0.067 (4)	0.071 (3)	0.081 (4)	−0.005 (3)	0.013 (3)	−0.008 (2)
C4	0.087 (4)	0.072 (3)	0.077 (4)	−0.022 (3)	0.034 (3)	−0.015 (3)
C5	0.105 (5)	0.064 (3)	0.051 (3)	−0.008 (3)	0.028 (3)	−0.007 (2)
C6	0.073 (3)	0.054 (3)	0.050 (3)	0.004 (2)	0.003 (2)	−0.0065 (18)
C7	0.061 (3)	0.058 (3)	0.042 (3)	0.002 (2)	0.004 (2)	−0.0011 (19)
C8	0.049 (3)	0.051 (2)	0.043 (2)	−0.0021 (18)	0.0048 (18)	−0.0021 (16)
C9	0.054 (3)	0.067 (3)	0.047 (2)	0.006 (2)	−0.005 (2)	0.0046 (19)
C10	0.048 (2)	0.062 (2)	0.060 (3)	0.002 (2)	−0.004 (2)	−0.004 (2)
C11	0.048 (3)	0.053 (2)	0.051 (3)	−0.003 (2)	0.0101 (19)	−0.0063 (19)
C12	0.054 (3)	0.051 (2)	0.041 (2)	−0.0049 (19)	0.005 (2)	0.0009 (16)
C13	0.044 (2)	0.050 (2)	0.041 (2)	−0.0013 (18)	−0.0014 (19)	−0.0004 (16)
C14	0.061 (3)	0.082 (3)	0.076 (4)	−0.011 (3)	0.022 (3)	−0.011 (3)

Cl1—C6	1.731 (5)	C4—C5	1.365 (8)
N1—O3	1.200 (5)	C4—H4	0.9300
N1—O4	1.221 (5)	C5—C6	1.400 (7)
N1—C13	1.464 (6)	C5—H5	0.9300
O1—C7	1.195 (6)	C8—C9	1.378 (6)
O2—C8	1.380 (5)	C8—C13	1.396 (6)
O2—C7	1.385 (6)	C9—C10	1.376 (6)
O5—C14	1.213 (7)	C9—H9	0.9300
C1—C6	1.385 (7)	C10—C11	1.388 (6)
C1—C2	1.408 (7)	C10—H10	0.9300
C1—C7	1.480 (6)	C11—C12	1.378 (6)
C2—C3	1.377 (7)	C11—C14	1.479 (7)
C2—H2	0.9300	C12—C13	1.387 (6)
C3—C4	1.370 (9)	C12—H12	0.9300
C3—H3	0.9300	C14—H14	1.10 (6)
O3—N1—O4	122.9 (4)	O1—C7—C1	128.7 (4)
O3—N1—C13	120.1 (4)	O2—C7—C1	109.1 (4)
O4—N1—C13	116.9 (4)	C9—C8—O2	121.3 (4)
C8—O2—C7	120.1 (3)	C9—C8—C13	119.3 (4)
C6—C1—C2	118.7 (5)	O2—C8—C13	119.3 (4)
C6—C1—C7	122.0 (4)	C10—C9—C8	120.1 (4)
C2—C1—C7	119.3 (4)	C10—C9—H9	120.0
C3—C2—C1	120.2 (5)	C8—C9—H9	120.0
C3—C2—H2	119.9	C9—C10—C11	120.8 (4)
C1—C2—H2	119.9	C9—C10—H10	119.6
C4—C3—C2	120.4 (6)	C11—C10—H10	119.6
C4—C3—H3	119.8	C12—C11—C10	119.7 (4)
C2—C3—H3	119.8	C12—C11—C14	120.0 (5)
C5—C4—C3	120.7 (5)	C10—C11—C14	120.3 (5)
C5—C4—H4	119.7	C11—C12—C13	119.6 (4)
C3—C4—H4	119.7	C11—C12—H12	120.2
C4—C5—C6	120.0 (5)	C13—C12—H12	120.2
C4—C5—H5	120.0	C12—C13—C8	120.6 (4)
C6—C5—H5	120.0	C12—C13—N1	116.6 (4)
C1—C6—C5	120.1 (5)	C8—C13—N1	122.9 (4)
C1—C6—Cl1	122.1 (4)	O5—C14—C11	123.7 (6)
C5—C6—Cl1	117.8 (4)	O5—C14—H14	122 (3)
O1—C7—O2	122.1 (4)	C11—C14—H14	114 (3)
C6—C1—C2—C3	−1.2 (6)	O2—C8—C9—C10	−175.0 (4)
C7—C1—C2—C3	176.6 (4)	C13—C8—C9—C10	−0.1 (6)
C1—C2—C3—C4	0.9 (7)	C8—C9—C10—C11	1.1 (6)
C2—C3—C4—C5	0.2 (8)	C9—C10—C11—C12	−1.6 (6)
C3—C4—C5—C6	−1.0 (8)	C9—C10—C11—C14	177.4 (4)
C2—C1—C6—C5	0.5 (6)	C10—C11—C12—C13	1.0 (6)
C7—C1—C6—C5	−177.2 (4)	C14—C11—C12—C13	−177.9 (4)
C2—C1—C6—Cl1	−177.3 (3)	C11—C12—C13—C8	−0.1 (6)
C7—C1—C6—Cl1	5.0 (6)	C11—C12—C13—N1	178.8 (3)
C4—C5—C6—C1	0.6 (7)	C9—C8—C13—C12	−0.4 (6)
C4—C5—C6—Cl1	178.5 (4)	O2—C8—C13—C12	174.6 (4)
C8—O2—C7—O1	−6.5 (7)	C9—C8—C13—N1	−179.2 (4)
C8—O2—C7—C1	175.7 (4)	O2—C8—C13—N1	−4.1 (6)
C6—C1—C7—O1	36.0 (7)	O3—N1—C13—C12	−161.5 (4)
C2—C1—C7—O1	−141.7 (5)	O4—N1—C13—C12	20.5 (6)
C6—C1—C7—O2	−146.4 (4)	O3—N1—C13—C8	17.3 (6)
C2—C1—C7—O2	35.9 (5)	O4—N1—C13—C8	−160.7 (4)
C7—O2—C8—C9	−51.7 (6)	C12—C11—C14—O5	3.7 (7)
C7—O2—C8—C13	133.4 (4)	C10—C11—C14—O5	−175.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O4i	1.10 (6)	2.48 (6)	3.381 (7)	138 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O4i	1.10 (6)	2.48 (6)	3.381 (7)	138 (4)

Symmetry code: (i) .