4-Formyl-2-nitro-phenyl 3-nitro-2-methyl-benzoate.

In the title formyl nitro aryl benzoate derivative, C15H10N2O7, the benzene rings form a dihedral angle of 4.96 (3)°. The mean plane of the central ester group, C-O-C-(=O)-C (r.m.s. deviation = 0.0484 Å), is twisted away from the formyl nitro aryl and benzoate rings by 46.61 (5) and 49.93 (5)°, respectively. In the crystal, the mol-ecules are packed forming C-H⋯O inter-actions in chains which propagate along [010]. Edge-fused R (3) 3(15) rings are generated along this direction.

Related literature

For similar formyl nitro aryl benzoate compounds, see: Moreno-Fuquen et al. (2013a ▶,b ▶). For information on hydrogen bonds, see: Nardelli (1995 ▶). For hydrogen-bond graph-sets motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C15H10N2O7

M = 330.25

Monoclinic,

a = 12.7162 (5) Å

b = 8.0719 (2) Å

c = 14.1156 (5) Å

β = 110.877 (4)°

V = 1353.76 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 123 K

0.35 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

6641 measured reflections

3319 independent reflections

2706 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.04

3319 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (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/S1600536813032583/ng5349sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032583/ng5349Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032583/ng5349Isup3.cml

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

C15H10N2O7	F(000) = 680
Mr = 330.25	Dx = 1.620 Mg m−3
Monoclinic, P21/c	Melting point: 398(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.7162 (5) Å	Cell parameters from 6641 reflections
b = 8.0719 (2) Å	θ = 3.0–29.5°
c = 14.1156 (5) Å	µ = 0.13 mm−1
β = 110.877 (4)°	T = 123 K
V = 1353.76 (8) Å3	Block, pale-yellow
Z = 4	0.35 × 0.30 × 0.20 mm

Oxford Diffraction Xcalibur E diffractometer	2706 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 29.5°, θmin = 3.0°
ω scans	h = −17→11
6641 measured reflections	k = −11→10
3319 independent reflections	l = −17→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0356P)2 + 0.5883P] where P = (Fo2 + 2Fc2)/3
3319 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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
O1	−0.02565 (8)	0.82147 (13)	0.96445 (8)	0.0165 (2)
O2	−0.00317 (8)	0.97501 (13)	0.83848 (7)	0.0149 (2)
O3	−0.14515 (10)	0.70025 (14)	0.76210 (9)	0.0245 (3)
O4	−0.27370 (10)	0.70420 (14)	0.83088 (10)	0.0283 (3)
O5	−0.44451 (10)	1.42910 (14)	0.70371 (9)	0.0253 (3)
O6	0.32188 (10)	0.37636 (14)	0.95119 (9)	0.0256 (3)
O7	0.45585 (9)	0.47549 (15)	1.08175 (8)	0.0246 (3)
N1	−0.20884 (10)	0.77299 (16)	0.79668 (10)	0.0187 (3)
N2	0.36621 (10)	0.48942 (16)	1.01005 (9)	0.0176 (3)
C1	0.15564 (12)	0.83319 (18)	0.94637 (10)	0.0137 (3)
C2	0.22771 (12)	0.96879 (18)	0.95875 (11)	0.0164 (3)
H2	0.1973	1.0774	0.9445	0.020*
C3	0.34317 (13)	0.94602 (19)	0.99163 (11)	0.0186 (3)
H3	0.3921	1.0386	1.0017	0.022*
C4	0.38658 (12)	0.78678 (19)	1.00971 (11)	0.0178 (3)
H4	0.4656	0.7689	1.0333	0.021*
C5	0.31330 (12)	0.65466 (18)	0.99296 (11)	0.0150 (3)
C6	0.19555 (12)	0.66950 (18)	0.96223 (10)	0.0136 (3)
C7	0.03361 (12)	0.87005 (17)	0.92016 (10)	0.0136 (3)
C8	−0.11021 (12)	1.04391 (18)	0.81185 (10)	0.0131 (3)
C9	−0.20853 (12)	0.95402 (18)	0.79489 (10)	0.0142 (3)
C10	−0.31127 (12)	1.03321 (18)	0.77283 (10)	0.0149 (3)
H10	−0.3771	0.9713	0.7660	0.018*
C11	−0.31668 (12)	1.20438 (18)	0.76078 (10)	0.0149 (3)
C12	−0.21895 (12)	1.29445 (18)	0.77370 (11)	0.0159 (3)
H12	−0.2231	1.4110	0.7638	0.019*
C13	−0.11619 (12)	1.21503 (18)	0.80080 (11)	0.0154 (3)
H13	−0.0495	1.2775	0.8119	0.018*
C14	−0.42791 (13)	1.2872 (2)	0.73352 (11)	0.0182 (3)
H14	−0.4883 (14)	1.218 (2)	0.7426 (12)	0.016 (4)*
C15	0.11801 (13)	0.52338 (19)	0.94709 (12)	0.0192 (3)
H15A	0.0404	0.5625	0.9296	0.029*
H15B	0.1396	0.4583	1.0097	0.029*
H15C	0.1234	0.4540	0.8920	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0153 (5)	0.0170 (5)	0.0176 (5)	0.0003 (4)	0.0063 (4)	0.0016 (4)
O2	0.0115 (5)	0.0170 (5)	0.0163 (5)	0.0026 (4)	0.0049 (4)	0.0043 (4)
O3	0.0241 (6)	0.0169 (6)	0.0302 (6)	0.0036 (5)	0.0069 (5)	−0.0063 (5)
O4	0.0231 (6)	0.0180 (6)	0.0434 (7)	−0.0044 (5)	0.0113 (5)	0.0059 (5)
O5	0.0229 (6)	0.0217 (6)	0.0284 (6)	0.0090 (5)	0.0058 (5)	0.0012 (5)
O6	0.0252 (6)	0.0184 (6)	0.0321 (6)	0.0025 (5)	0.0090 (5)	−0.0027 (5)
O7	0.0176 (6)	0.0309 (7)	0.0229 (6)	0.0082 (5)	0.0041 (5)	0.0080 (5)
N1	0.0156 (6)	0.0138 (6)	0.0220 (7)	−0.0015 (5)	0.0009 (5)	−0.0005 (5)
N2	0.0155 (6)	0.0202 (7)	0.0188 (6)	0.0041 (5)	0.0082 (5)	0.0040 (5)
C1	0.0130 (7)	0.0165 (7)	0.0119 (6)	0.0006 (6)	0.0048 (5)	−0.0002 (5)
C2	0.0177 (7)	0.0148 (7)	0.0172 (7)	0.0006 (6)	0.0070 (6)	0.0001 (6)
C3	0.0160 (7)	0.0184 (8)	0.0210 (7)	−0.0037 (6)	0.0063 (6)	−0.0015 (6)
C4	0.0124 (7)	0.0224 (8)	0.0186 (7)	0.0005 (6)	0.0054 (6)	−0.0004 (6)
C5	0.0153 (7)	0.0163 (7)	0.0136 (7)	0.0037 (6)	0.0055 (5)	0.0022 (6)
C6	0.0127 (7)	0.0164 (7)	0.0118 (6)	0.0000 (6)	0.0045 (5)	0.0004 (5)
C7	0.0132 (7)	0.0115 (7)	0.0145 (7)	0.0009 (5)	0.0031 (5)	−0.0010 (5)
C8	0.0117 (7)	0.0158 (7)	0.0117 (6)	0.0026 (5)	0.0043 (5)	0.0009 (5)
C9	0.0161 (7)	0.0103 (7)	0.0153 (7)	−0.0009 (5)	0.0045 (5)	−0.0001 (5)
C10	0.0126 (7)	0.0166 (7)	0.0148 (7)	−0.0013 (6)	0.0041 (5)	0.0000 (6)
C11	0.0151 (7)	0.0163 (7)	0.0120 (7)	0.0022 (6)	0.0032 (5)	−0.0011 (5)
C12	0.0187 (7)	0.0123 (7)	0.0156 (7)	0.0016 (6)	0.0047 (6)	0.0005 (5)
C13	0.0151 (7)	0.0152 (7)	0.0151 (7)	−0.0026 (6)	0.0045 (5)	0.0004 (5)
C14	0.0161 (7)	0.0204 (8)	0.0164 (7)	0.0026 (6)	0.0038 (6)	−0.0037 (6)
C15	0.0162 (7)	0.0152 (8)	0.0263 (8)	−0.0004 (6)	0.0078 (6)	0.0022 (6)

O1—C7	1.2034 (17)	C4—H4	0.9500
O2—C7	1.3717 (17)	C5—C6	1.408 (2)
O2—C8	1.3923 (16)	C6—C15	1.503 (2)
O3—N1	1.2333 (16)	C8—C13	1.389 (2)
O4—N1	1.2269 (16)	C8—C9	1.391 (2)
O5—C14	1.2123 (19)	C9—C10	1.387 (2)
O6—N2	1.2276 (17)	C10—C11	1.391 (2)
O7—N2	1.2305 (16)	C10—H10	0.9500
N1—C9	1.4615 (19)	C11—C12	1.395 (2)
N2—C5	1.4745 (19)	C11—C14	1.486 (2)
C1—C2	1.398 (2)	C12—C13	1.381 (2)
C1—C6	1.405 (2)	C12—H12	0.9500
C1—C7	1.4913 (19)	C13—H13	0.9500
C2—C3	1.385 (2)	C14—H14	0.992 (17)
C2—H2	0.9500	C15—H15A	0.9800
C3—C4	1.386 (2)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.380 (2)
C7—O2—C8	118.77 (11)	C13—C8—C9	119.32 (13)
O4—N1—O3	124.66 (13)	C13—C8—O2	115.89 (13)
O4—N1—C9	117.76 (13)	C9—C8—O2	124.79 (13)
O3—N1—C9	117.57 (12)	C10—C9—C8	121.03 (13)
O6—N2—O7	123.78 (13)	C10—C9—N1	117.17 (13)
O6—N2—C5	119.28 (12)	C8—C9—N1	121.78 (13)
O7—N2—C5	116.88 (13)	C9—C10—C11	119.15 (14)
C2—C1—C6	122.21 (13)	C9—C10—H10	120.4
C2—C1—C7	116.91 (13)	C11—C10—H10	120.4
C6—C1—C7	120.81 (13)	C10—C11—C12	119.93 (14)
C3—C2—C1	120.48 (14)	C10—C11—C14	118.67 (14)
C3—C2—H2	119.8	C12—C11—C14	121.39 (14)
C1—C2—H2	119.8	C13—C12—C11	120.34 (14)
C2—C3—C4	119.32 (14)	C13—C12—H12	119.8
C2—C3—H3	120.3	C11—C12—H12	119.8
C4—C3—H3	120.3	C12—C13—C8	120.07 (14)
C5—C4—C3	118.99 (14)	C12—C13—H13	120.0
C5—C4—H4	120.5	C8—C13—H13	120.0
C3—C4—H4	120.5	O5—C14—C11	123.16 (15)
C4—C5—C6	124.48 (14)	O5—C14—H14	121.8 (10)
C4—C5—N2	115.48 (13)	C11—C14—H14	115.0 (10)
C6—C5—N2	120.04 (13)	C6—C15—H15A	109.5
C1—C6—C5	114.42 (13)	C6—C15—H15B	109.5
C1—C6—C15	122.28 (13)	H15A—C15—H15B	109.5
C5—C6—C15	123.30 (13)	C6—C15—H15C	109.5
O1—C7—O2	123.29 (13)	H15A—C15—H15C	109.5
O1—C7—C1	126.50 (13)	H15B—C15—H15C	109.5
O2—C7—C1	110.16 (12)
C6—C1—C2—C3	−2.7 (2)	C6—C1—C7—O2	−131.49 (13)
C7—C1—C2—C3	174.41 (13)	C7—O2—C8—C13	128.15 (13)
C1—C2—C3—C4	1.6 (2)	C7—O2—C8—C9	−52.74 (18)
C2—C3—C4—C5	1.0 (2)	C13—C8—C9—C10	−3.7 (2)
C3—C4—C5—C6	−2.8 (2)	O2—C8—C9—C10	177.22 (12)
C3—C4—C5—N2	177.60 (13)	C13—C8—C9—N1	174.58 (13)
O6—N2—C5—C4	−139.54 (14)	O2—C8—C9—N1	−4.5 (2)
O7—N2—C5—C4	37.86 (17)	O4—N1—C9—C10	−37.16 (19)
O6—N2—C5—C6	40.80 (19)	O3—N1—C9—C10	141.65 (13)
O7—N2—C5—C6	−141.79 (14)	O4—N1—C9—C8	144.49 (14)
C2—C1—C6—C5	1.0 (2)	O3—N1—C9—C8	−36.7 (2)
C7—C1—C6—C5	−175.99 (12)	C8—C9—C10—C11	4.4 (2)
C2—C1—C6—C15	−178.84 (13)	N1—C9—C10—C11	−173.94 (13)
C7—C1—C6—C15	4.2 (2)	C9—C10—C11—C12	−1.8 (2)
C4—C5—C6—C1	1.7 (2)	C9—C10—C11—C14	177.84 (13)
N2—C5—C6—C1	−178.63 (12)	C10—C11—C12—C13	−1.5 (2)
C4—C5—C6—C15	−178.42 (14)	C14—C11—C12—C13	178.86 (13)
N2—C5—C6—C15	1.2 (2)	C11—C12—C13—C8	2.3 (2)
C8—O2—C7—O1	7.4 (2)	C9—C8—C13—C12	0.3 (2)
C8—O2—C7—C1	−170.43 (12)	O2—C8—C13—C12	179.48 (12)
C2—C1—C7—O1	−126.35 (16)	C10—C11—C14—O5	−166.20 (14)
C6—C1—C7—O1	50.8 (2)	C12—C11—C14—O5	13.4 (2)
C2—C1—C7—O2	51.37 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O5i	0.95	2.48	3.3457 (18)	152
C12—H12···O4ii	0.95	2.71	3.5321 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O5i	0.95	2.48	3.3457 (18)	152
C12—H12⋯O4ii	0.95	2.71	3.5321 (19)	145

Symmetry codes: (i) ; (ii) .