4-Formyl-2-nitro-phenyl benzoate.

In the title nitroaryl benzoate derivative, C14H9NO5, the aromatic rings form a dihedral angle of 46.37 (8)°. The central ester moiety, -C-(C=O)-O-, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0283 Å) and forms a dihedral angle of 54.06 (9)° with the 4-formyl-2-nitro-phenyl ring and 7.99 (19)° with the benzoate ring. In the crystal, mol-ecules are inter-twined by weak C-H⋯O inter-actions, forming helical chains along [100].

Related literature

For similar esters, see: Moreno-Fuquen et al. (2013a ▶,b ▶, 2014 ▶). For hydrogen bonding, see: Nardelli (1995 ▶) and for hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C14H9NO5

M = 271.22

Monoclinic,

a = 11.3478 (11) Å

b = 3.7101 (5) Å

c = 27.723 (2) Å

β = 94.979 (9)°

V = 1162.8 (2) Å3

Z = 4

Cu Kα radiation

μ = 1.02 mm−1

T = 123 K

0.21 × 0.12 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.813, T max = 1.000

4231 measured reflections

2213 independent reflections

1403 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.190

S = 0.99

2213 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 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/S1600536814002694/hg5380sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002694/hg5380Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002694/hg5380Isup3.cml

CCDC reference:

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

C14H9NO5	F(000) = 560
Mr = 271.22	Dx = 1.549 Mg m−3
Monoclinic, P21/c	Melting point: 457(1) K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54180 Å
a = 11.3478 (11) Å	Cell parameters from 977 reflections
b = 3.7101 (5) Å	θ = 3.9–73.3°
c = 27.723 (2) Å	µ = 1.02 mm−1
β = 94.979 (9)°	T = 123 K
V = 1162.8 (2) Å3	Plate, colourless
Z = 4	0.21 × 0.12 × 0.02 mm

Oxford Diffraction Xcalibur E diffractometer	2213 independent reflections
Radiation source: fine-focus sealed tube	1403 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 70.0°, θmin = 3.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	h = −10→13
Tmin = 0.813, Tmax = 1.000	k = −4→4
4231 measured reflections	l = −33→33

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.190	w = 1/[σ2(Fo2) + (0.0857P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
2213 reflections	Δρmax = 0.37 e Å−3
186 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (7)

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	0.89645 (19)	0.3296 (7)	0.43051 (7)	0.0419 (7)
O2	0.73248 (18)	0.0150 (7)	0.40350 (7)	0.0398 (6)
O5	0.8819 (2)	−0.0584 (8)	0.18661 (8)	0.0510 (8)
O3	0.5482 (2)	0.4580 (8)	0.37507 (8)	0.0457 (7)
O4	0.46029 (19)	0.1854 (8)	0.31290 (7)	0.0462 (7)
N1	0.5497 (2)	0.2761 (9)	0.33830 (9)	0.0374 (7)
C7	0.8124 (3)	0.1534 (10)	0.43947 (10)	0.0356 (8)
C1	0.7763 (3)	0.0601 (10)	0.48775 (11)	0.0363 (8)
C2	0.6678 (3)	−0.1079 (9)	0.49328 (11)	0.0370 (8)
H2	0.6164	−0.1707	0.4657	0.044*
C3	0.6360 (3)	−0.1820 (11)	0.53964 (11)	0.0404 (8)
H3	0.5626	−0.2956	0.5439	0.048*
C4	0.7118 (3)	−0.0895 (10)	0.57954 (12)	0.0441 (9)
H4	0.6897	−0.1382	0.6112	0.053*
C5	0.8190 (3)	0.0722 (11)	0.57390 (11)	0.0436 (9)
H5	0.8708	0.1306	0.6016	0.052*
C6	0.8514 (3)	0.1497 (10)	0.52809 (11)	0.0393 (8)
H6	0.9249	0.2641	0.5243	0.047*
C8	0.7551 (3)	0.0466 (10)	0.35567 (11)	0.0353 (8)
C9	0.6635 (3)	0.1614 (10)	0.32282 (11)	0.0345 (8)
C10	0.6769 (3)	0.1666 (10)	0.27316 (11)	0.0364 (8)
H10	0.6138	0.2447	0.2508	0.044*
C11	0.7821 (3)	0.0577 (10)	0.25704 (11)	0.0369 (8)
C12	0.8741 (3)	−0.0597 (10)	0.29011 (11)	0.0375 (8)
H12	0.9469	−0.1342	0.2788	0.045*
C13	0.8601 (3)	−0.0684 (10)	0.33923 (11)	0.0380 (8)
H13	0.9224	−0.1530	0.3615	0.046*
C14	0.7966 (3)	0.0616 (11)	0.20439 (11)	0.0399 (9)
H14	0.731 (3)	0.180 (10)	0.1847 (11)	0.039 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0400 (13)	0.0533 (16)	0.0313 (12)	−0.0048 (12)	−0.0026 (10)	0.0012 (11)
O2	0.0384 (12)	0.0560 (16)	0.0233 (11)	−0.0044 (11)	−0.0075 (9)	0.0031 (11)
O5	0.0475 (15)	0.072 (2)	0.0329 (12)	0.0034 (14)	−0.0016 (11)	−0.0037 (13)
O3	0.0450 (14)	0.0584 (18)	0.0329 (12)	−0.0017 (12)	−0.0009 (10)	−0.0091 (12)
O4	0.0376 (13)	0.0667 (19)	0.0322 (12)	0.0026 (12)	−0.0085 (10)	−0.0034 (12)
N1	0.0377 (15)	0.0472 (18)	0.0259 (12)	0.0007 (13)	−0.0056 (11)	0.0023 (13)
C7	0.0355 (17)	0.043 (2)	0.0264 (15)	0.0041 (15)	−0.0074 (13)	−0.0006 (15)
C1	0.0355 (17)	0.045 (2)	0.0271 (16)	0.0055 (15)	−0.0036 (13)	0.0026 (15)
C2	0.0397 (18)	0.041 (2)	0.0283 (16)	0.0030 (15)	−0.0070 (13)	0.0004 (15)
C3	0.0380 (17)	0.047 (2)	0.0353 (17)	0.0033 (16)	0.0003 (14)	0.0018 (16)
C4	0.047 (2)	0.054 (2)	0.0310 (16)	0.0024 (18)	−0.0013 (14)	0.0038 (17)
C5	0.0449 (19)	0.055 (2)	0.0281 (16)	0.0046 (17)	−0.0122 (14)	−0.0049 (16)
C6	0.0365 (17)	0.048 (2)	0.0320 (16)	0.0003 (16)	−0.0038 (13)	0.0022 (16)
C8	0.0381 (17)	0.0407 (19)	0.0258 (15)	−0.0061 (15)	−0.0051 (13)	0.0036 (14)
C9	0.0332 (16)	0.0404 (19)	0.0285 (15)	−0.0025 (15)	−0.0051 (12)	−0.0003 (15)
C10	0.0362 (17)	0.044 (2)	0.0266 (15)	−0.0005 (16)	−0.0091 (13)	0.0055 (15)
C11	0.0383 (18)	0.044 (2)	0.0271 (15)	−0.0036 (15)	−0.0043 (13)	−0.0019 (15)
C12	0.0363 (17)	0.042 (2)	0.0333 (16)	−0.0043 (15)	−0.0043 (13)	−0.0043 (15)
C13	0.0384 (17)	0.044 (2)	0.0292 (16)	−0.0008 (15)	−0.0087 (13)	0.0034 (15)
C14	0.0382 (18)	0.050 (2)	0.0301 (17)	−0.0024 (16)	−0.0064 (14)	0.0008 (16)

O1—C7	1.200 (4)	C4—H4	0.9500
O2—C8	1.377 (4)	C5—C6	1.383 (5)
O2—C7	1.387 (3)	C5—H5	0.9500
O5—C14	1.208 (4)	C6—H6	0.9500
O3—N1	1.224 (3)	C8—C13	1.380 (5)
O4—N1	1.231 (3)	C8—C9	1.388 (4)
N1—C9	1.459 (4)	C9—C10	1.398 (4)
C7—C1	1.475 (4)	C10—C11	1.372 (4)
C1—C6	1.387 (4)	C10—H10	0.9500
C1—C2	1.399 (5)	C11—C12	1.398 (4)
C2—C3	1.392 (4)	C11—C14	1.483 (4)
C2—H2	0.9500	C12—C13	1.385 (4)
C3—C4	1.384 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.377 (5)	C14—H14	0.99 (3)
C8—O2—C7	119.7 (3)	C5—C6—H6	120.1
O3—N1—O4	123.9 (3)	C1—C6—H6	120.1
O3—N1—C9	118.8 (2)	O2—C8—C13	122.0 (3)
O4—N1—C9	117.3 (3)	O2—C8—C9	117.8 (3)
O1—C7—O2	122.3 (3)	C13—C8—C9	119.8 (3)
O1—C7—C1	127.2 (3)	C8—C9—C10	120.8 (3)
O2—C7—C1	110.5 (3)	C8—C9—N1	121.9 (3)
C6—C1—C2	120.2 (3)	C10—C9—N1	117.4 (3)
C6—C1—C7	118.4 (3)	C11—C10—C9	119.3 (3)
C2—C1—C7	121.4 (3)	C11—C10—H10	120.4
C3—C2—C1	119.3 (3)	C9—C10—H10	120.4
C3—C2—H2	120.3	C10—C11—C12	120.0 (3)
C1—C2—H2	120.3	C10—C11—C14	119.5 (3)
C4—C3—C2	119.7 (3)	C12—C11—C14	120.5 (3)
C4—C3—H3	120.1	C13—C12—C11	120.6 (3)
C2—C3—H3	120.1	C13—C12—H12	119.7
C5—C4—C3	120.7 (3)	C11—C12—H12	119.7
C5—C4—H4	119.6	C8—C13—C12	119.6 (3)
C3—C4—H4	119.6	C8—C13—H13	120.2
C4—C5—C6	120.2 (3)	C12—C13—H13	120.2
C4—C5—H5	119.9	O5—C14—C11	124.0 (3)
C6—C5—H5	119.9	O5—C14—H14	122.0 (19)
C5—C6—C1	119.8 (3)	C11—C14—H14	114.0 (19)
C8—O2—C7—O1	6.7 (5)	O2—C8—C9—N1	5.3 (5)
C8—O2—C7—C1	−174.7 (3)	C13—C8—C9—N1	178.3 (3)
O1—C7—C1—C6	−7.0 (6)	O3—N1—C9—C8	40.2 (5)
O2—C7—C1—C6	174.5 (3)	O4—N1—C9—C8	−140.5 (3)
O1—C7—C1—C2	171.6 (4)	O3—N1—C9—C10	−140.6 (3)
O2—C7—C1—C2	−6.9 (5)	O4—N1—C9—C10	38.6 (5)
C6—C1—C2—C3	0.3 (5)	C8—C9—C10—C11	−0.2 (5)
C7—C1—C2—C3	−178.2 (3)	N1—C9—C10—C11	−179.4 (3)
C1—C2—C3—C4	−0.1 (5)	C9—C10—C11—C12	0.5 (5)
C2—C3—C4—C5	−0.6 (6)	C9—C10—C11—C14	179.8 (3)
C3—C4—C5—C6	1.1 (6)	C10—C11—C12—C13	0.2 (5)
C4—C5—C6—C1	−0.8 (6)	C14—C11—C12—C13	−179.1 (3)
C2—C1—C6—C5	0.1 (6)	O2—C8—C13—C12	174.3 (3)
C7—C1—C6—C5	178.7 (3)	C9—C8—C13—C12	1.6 (5)
C7—O2—C8—C13	53.3 (5)	C11—C12—C13—C8	−1.3 (5)
C7—O2—C8—C9	−133.8 (3)	C10—C11—C14—O5	−173.3 (4)
O2—C8—C9—C10	−173.9 (3)	C12—C11—C14—O5	5.9 (6)
C13—C8—C9—C10	−0.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O4i	0.95	2.50	3.343 (4)	148
C12—H12···O5ii	0.95	2.62	3.346 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O4i	0.95	2.50	3.343 (4)	148
C12—H12⋯O5ii	0.95	2.62	3.346 (4)	134

Symmetry codes: (i) ; (ii) .