4-Methyl-3-nitro-benzaldehyde.

In the crystal structure of the title compound, C(8)H(7)NO(3), mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonding.

Related literature

For the preparation, see: Johnson et al. (1991 ▶). For general background to supra­molecular electron-transfer materials, see: Yagi et al. (2003 ▶); Ezoe et al. (2006 ▶); Normand-Bayle et al. (2005 ▶); Ward et al. (2005 ▶). For a related structure, see: Zhang et al. (2009 ▶).

Experimental

Crystal data

C8H7NO3

M = 165.15

Monoclinic,

a = 3.9052 (6) Å

b = 17.841 (3) Å

c = 11.0663 (15) Å

β = 97.647 (2)°

V = 764.14 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.32 × 0.20 × 0.12 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.745, T max = 1.000

4088 measured reflections

1353 independent reflections

1012 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.114

S = 1.05

1353 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033635/lx2167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033635/lx2167Isup2.hkl

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

C8H7NO3	F(000) = 344
Mr = 165.15	Dx = 1.435 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1083 reflections
a = 3.9052 (6) Å	θ = 2.2–23.9°
b = 17.841 (3) Å	µ = 0.11 mm−1
c = 11.0663 (15) Å	T = 293 K
β = 97.647 (2)°	Block, colorless
V = 764.14 (19) Å3	0.32 × 0.20 × 0.12 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	1353 independent reflections
Radiation source: fine-focus sealed tube	1012 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −4→4
Tmin = 0.745, Tmax = 1.000	k = −21→18
4088 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.1376P] where P = (Fo2 + 2Fc2)/3
1353 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.16 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	1.3758 (4)	0.60008 (9)	1.06104 (12)	0.0824 (5)
O2	1.0886 (5)	0.70092 (9)	1.05565 (14)	0.0976 (6)
O3	0.8183 (5)	0.42460 (9)	0.60139 (14)	0.0937 (6)
N1	1.1695 (4)	0.64374 (9)	1.00814 (13)	0.0537 (4)
C1	0.7588 (6)	0.75833 (11)	0.8424 (2)	0.0680 (6)
H1A	0.6294	0.7831	0.7740	0.102*
H1B	0.9756	0.7835	0.8638	0.102*
H1C	0.6300	0.7594	0.9105	0.102*
C2	0.8234 (4)	0.67836 (9)	0.80931 (16)	0.0479 (4)
C3	0.6869 (5)	0.65315 (10)	0.69353 (16)	0.0549 (5)
H3	0.5619	0.6866	0.6403	0.066*
C4	0.7290 (5)	0.58141 (10)	0.65495 (15)	0.0546 (5)
H4	0.6312	0.5669	0.5772	0.065*
C5	0.9177 (4)	0.52988 (10)	0.73139 (14)	0.0483 (4)
C6	0.9618 (5)	0.45197 (11)	0.69313 (17)	0.0640 (5)
H6	1.1124	0.4217	0.7440	0.077*
C7	1.0625 (4)	0.55297 (9)	0.84592 (14)	0.0458 (4)
H7	1.1943	0.5197	0.8975	0.055*
C8	1.0119 (4)	0.62533 (9)	0.88392 (14)	0.0440 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0988 (12)	0.0828 (11)	0.0565 (9)	0.0162 (9)	−0.0233 (8)	−0.0012 (7)
O2	0.1323 (15)	0.0757 (11)	0.0757 (11)	0.0201 (10)	−0.0198 (10)	−0.0281 (9)
O3	0.1213 (14)	0.0757 (11)	0.0727 (10)	0.0141 (9)	−0.0293 (9)	−0.0225 (8)
N1	0.0589 (9)	0.0527 (9)	0.0476 (8)	−0.0074 (7)	0.0000 (7)	−0.0003 (7)
C1	0.0713 (13)	0.0501 (11)	0.0811 (14)	0.0055 (9)	0.0046 (11)	0.0069 (10)
C2	0.0438 (9)	0.0461 (10)	0.0540 (10)	−0.0021 (7)	0.0074 (8)	0.0087 (7)
C3	0.0530 (10)	0.0593 (12)	0.0504 (10)	0.0036 (8)	−0.0001 (8)	0.0172 (8)
C4	0.0554 (11)	0.0646 (12)	0.0412 (9)	−0.0009 (9)	−0.0028 (8)	0.0046 (8)
C5	0.0472 (10)	0.0536 (10)	0.0429 (9)	−0.0010 (7)	0.0011 (7)	0.0010 (7)
C6	0.0730 (13)	0.0625 (13)	0.0527 (11)	0.0082 (10)	−0.0063 (9)	−0.0047 (9)
C7	0.0439 (9)	0.0480 (10)	0.0438 (9)	0.0007 (7)	0.0000 (7)	0.0072 (7)
C8	0.0427 (9)	0.0488 (10)	0.0396 (9)	−0.0064 (7)	0.0028 (7)	0.0046 (7)

O1—N1	1.2135 (19)	C3—C4	1.366 (3)
O2—N1	1.209 (2)	C3—H3	0.9300
O3—C6	1.197 (2)	C4—C5	1.392 (2)
N1—C8	1.467 (2)	C4—H4	0.9300
C1—C2	1.503 (2)	C5—C7	1.380 (2)
C1—H1A	0.9600	C5—C6	1.470 (3)
C1—H1B	0.9600	C6—H6	0.9300
C1—H1C	0.9600	C7—C8	1.380 (2)
C2—C3	1.395 (2)	C7—H7	0.9300
C2—C8	1.399 (2)
O2—N1—O1	121.80 (16)	C3—C4—C5	120.32 (16)
O2—N1—C8	119.68 (16)	C3—C4—H4	119.8
O1—N1—C8	118.51 (15)	C5—C4—H4	119.8
C2—C1—H1A	109.5	C7—C5—C4	118.69 (17)
C2—C1—H1B	109.5	C7—C5—C6	119.82 (16)
H1A—C1—H1B	109.5	C4—C5—C6	121.49 (16)
C2—C1—H1C	109.5	O3—C6—C5	124.79 (18)
H1A—C1—H1C	109.5	O3—C6—H6	117.6
H1B—C1—H1C	109.5	C5—C6—H6	117.6
C3—C2—C8	115.51 (16)	C5—C7—C8	120.08 (15)
C3—C2—C1	118.29 (16)	C5—C7—H7	120.0
C8—C2—C1	126.21 (16)	C8—C7—H7	120.0
C4—C3—C2	122.81 (16)	C7—C8—C2	122.57 (15)
C4—C3—H3	118.6	C7—C8—N1	115.84 (14)
C2—C3—H3	118.6	C2—C8—N1	121.59 (15)
C8—C2—C3—C4	0.8 (3)	C5—C7—C8—N1	178.59 (14)
C1—C2—C3—C4	−179.54 (18)	C3—C2—C8—C7	0.4 (2)
C2—C3—C4—C5	−0.7 (3)	C1—C2—C8—C7	−179.27 (16)
C3—C4—C5—C7	−0.5 (3)	C3—C2—C8—N1	−179.79 (14)
C3—C4—C5—C6	178.88 (17)	C1—C2—C8—N1	0.5 (3)
C7—C5—C6—O3	172.0 (2)	O2—N1—C8—C7	−167.19 (17)
C4—C5—C6—O3	−7.4 (3)	O1—N1—C8—C7	11.8 (2)
C4—C5—C7—C8	1.6 (2)	O2—N1—C8—C2	13.0 (3)
C6—C5—C7—C8	−177.77 (16)	O1—N1—C8—C2	−167.98 (17)
C5—C7—C8—C2	−1.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3i	0.93	2.47	3.319 (2)	152.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3i	0.93	2.47	3.319 (2)	152

Symmetry code: (i) .