Methyl 4-nitro-benzoate.

In the mol-ecule of the title compound, C(8)H(7)NO(4), the nitro group is approximately coplanar with the benzene ring [dihedral angle = 0.6 (1)°], while the dihedral angle between the methoxy-carbonyl group and the benzene ring is 8.8 (1)°. In the crystal structure, weak inter-molecular aromatic C-H⋯O(carbox-yl) and C-H⋯O(nitro) hydrogen-bonding inter-actions are present.

Related literature

For related literature on benzoates, see: Zhang (1992 ▶); Zhang et al. (1990 ▶); Zhang et al. (1995 ▶).

Experimental

Crystal data

C8H7NO4

M = 181.15

Monoclinic,

a = 7.109 (3) Å

b = 17.092 (6) Å

c = 7.193 (3) Å

β = 116.292 (4)°

V = 783.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 93 K

0.43 × 0.40 × 0.10 mm

Data collection

Rigaku SPIDER CCD-detector diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.948, T max = 0.988

6176 measured reflections

1787 independent reflections

1445 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.080

S = 1.00

1787 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.18 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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 I, global. DOI: 10.1107/S160053680904745X/zs2018sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904745X/zs2018Isup2.hkl

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

C8H7NO4	F(000) = 376
Mr = 181.15	Dx = 1.536 Mg m−3
Monoclinic, P21/c	Melting point: 369(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.109 (3) Å	Cell parameters from 2257 reflections
b = 17.092 (6) Å	θ = 3.2–27.4°
c = 7.193 (3) Å	µ = 0.13 mm−1
β = 116.292 (4)°	T = 93 K
V = 783.6 (5) Å3	Plate, colorless
Z = 4	0.43 × 0.40 × 0.10 mm

Rigaku SPIDER CCD-detector diffractometer	1787 independent reflections
Radiation source: rotating anode	1445 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: ψ scan (North et al., 1968)	h = −9→9
Tmin = 0.948, Tmax = 0.988	k = −20→22
6176 measured reflections	l = −9→9

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0303P)2 + 0.336P] where P = (Fo2 + 2Fc2)/3
1787 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.18 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
O1	0.35100 (15)	0.66883 (5)	0.67509 (14)	0.0205 (2)
O2	0.30933 (15)	0.59510 (5)	0.91414 (14)	0.0216 (2)
O3	0.14128 (16)	0.28185 (5)	0.23700 (16)	0.0265 (2)
O4	0.14076 (17)	0.36321 (6)	0.00524 (15)	0.0275 (2)
N1	0.15702 (17)	0.34819 (6)	0.17881 (17)	0.0185 (2)
C1	0.25319 (19)	0.54972 (7)	0.39808 (19)	0.0155 (3)
H1	0.2638	0.6016	0.3563	0.019*
C2	0.21513 (19)	0.48826 (7)	0.2601 (2)	0.0160 (3)
H2	0.2007	0.4971	0.1240	0.019*
C3	0.19872 (19)	0.41347 (7)	0.3264 (2)	0.0155 (3)
C4	0.21927 (19)	0.39748 (7)	0.5240 (2)	0.0167 (3)
H4	0.2065	0.3456	0.5643	0.020*
C5	0.25907 (19)	0.45958 (7)	0.6606 (2)	0.0160 (3)
H5	0.2749	0.4503	0.7970	0.019*
C6	0.27592 (18)	0.53560 (7)	0.59852 (19)	0.0149 (3)
C7	0.31372 (19)	0.60132 (7)	0.7484 (2)	0.0162 (3)
C8	0.3760 (2)	0.73724 (8)	0.8036 (2)	0.0239 (3)
H8A	0.2532	0.7425	0.8310	0.029*
H8B	0.3890	0.7840	0.7313	0.029*
H8C	0.5025	0.7314	0.9351	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0302 (5)	0.0155 (5)	0.0190 (5)	−0.0039 (4)	0.0139 (4)	−0.0029 (4)
O2	0.0259 (5)	0.0241 (5)	0.0167 (5)	−0.0026 (4)	0.0111 (4)	−0.0005 (4)
O3	0.0390 (6)	0.0150 (5)	0.0290 (6)	−0.0025 (4)	0.0182 (5)	0.0006 (4)
O4	0.0437 (6)	0.0225 (5)	0.0202 (5)	−0.0009 (5)	0.0177 (5)	−0.0016 (4)
N1	0.0196 (5)	0.0163 (5)	0.0211 (6)	0.0005 (4)	0.0102 (5)	0.0002 (4)
C1	0.0151 (6)	0.0144 (6)	0.0172 (7)	−0.0002 (5)	0.0075 (5)	0.0022 (5)
C2	0.0152 (6)	0.0189 (6)	0.0142 (6)	0.0007 (5)	0.0067 (5)	0.0024 (5)
C3	0.0132 (6)	0.0160 (6)	0.0172 (6)	0.0011 (5)	0.0066 (5)	−0.0008 (5)
C4	0.0152 (6)	0.0153 (6)	0.0204 (7)	0.0008 (5)	0.0088 (5)	0.0033 (5)
C5	0.0143 (6)	0.0196 (6)	0.0150 (6)	0.0012 (5)	0.0071 (5)	0.0036 (5)
C6	0.0115 (5)	0.0175 (6)	0.0152 (6)	0.0003 (5)	0.0055 (5)	−0.0002 (5)
C7	0.0134 (6)	0.0181 (6)	0.0162 (6)	0.0005 (5)	0.0059 (5)	0.0017 (5)
C8	0.0339 (8)	0.0176 (6)	0.0243 (7)	−0.0055 (6)	0.0167 (6)	−0.0060 (5)

O1—C7	1.3429 (15)	C2—H2	0.9500
O1—C8	1.4517 (15)	C3—C4	1.3901 (18)
O2—C7	1.2111 (16)	C4—C5	1.3880 (18)
O3—N1	1.2308 (14)	C4—H4	0.9500
O4—N1	1.2290 (15)	C5—C6	1.3962 (18)
N1—C3	1.4770 (16)	C5—H5	0.9500
C1—C2	1.3872 (18)	C6—C7	1.4965 (18)
C1—C6	1.3988 (18)	C8—H8A	0.9800
C1—H1	0.9500	C8—H8B	0.9800
C2—C3	1.3873 (17)	C8—H8C	0.9800
C7—O1—C8	115.59 (10)	C4—C5—C6	120.30 (12)
O4—N1—O3	123.79 (11)	C4—C5—H5	119.8
O4—N1—C3	118.11 (10)	C6—C5—H5	119.8
O3—N1—C3	118.10 (11)	C5—C6—C1	120.22 (12)
C2—C1—C6	120.25 (12)	C5—C6—C7	118.78 (11)
C2—C1—H1	119.9	C1—C6—C7	120.98 (11)
C6—C1—H1	119.9	O2—C7—O1	123.89 (12)
C1—C2—C3	118.10 (12)	O2—C7—C6	124.65 (11)
C1—C2—H2	121.0	O1—C7—C6	111.46 (11)
C3—C2—H2	121.0	O1—C8—H8A	109.5
C2—C3—C4	123.11 (12)	O1—C8—H8B	109.5
C2—C3—N1	118.00 (11)	H8A—C8—H8B	109.5
C4—C3—N1	118.89 (11)	O1—C8—H8C	109.5
C5—C4—C3	118.01 (12)	H8A—C8—H8C	109.5
C5—C4—H4	121.0	H8B—C8—H8C	109.5
C3—C4—H4	121.0
C6—C1—C2—C3	0.59 (18)	C4—C5—C6—C1	−0.12 (18)
C1—C2—C3—C4	−0.22 (18)	C4—C5—C6—C7	178.53 (11)
C1—C2—C3—N1	179.66 (11)	C2—C1—C6—C5	−0.43 (18)
O4—N1—C3—C2	0.62 (17)	C2—C1—C6—C7	−179.05 (11)
O3—N1—C3—C2	−179.62 (11)	C8—O1—C7—O2	−3.17 (18)
O4—N1—C3—C4	−179.49 (12)	C8—O1—C7—C6	176.11 (10)
O3—N1—C3—C4	0.27 (17)	C5—C6—C7—O2	−8.15 (19)
C2—C3—C4—C5	−0.31 (18)	C1—C6—C7—O2	170.48 (12)
N1—C3—C4—C5	179.80 (11)	C5—C6—C7—O1	172.58 (11)
C3—C4—C5—C6	0.48 (18)	C1—C6—C7—O1	−8.78 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.95	2.39	2.7149 (19)	100
C2—H2···O2i	0.95	2.59	3.384 (2)	141
C5—H5···O4ii	0.95	2.58	3.378 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.59	3.384 (2)	141
C5—H5⋯O4ii	0.95	2.58	3.378 (2)	142

Symmetry codes: (i) ; (ii) .