Dimethyl 5-nitro-isophthalate.

The nitro group in the title compound, C(10)H(9)NO(6), is rotated by 10.9 (5)° out of the plane of the benzene ring.

Related literature

For related literature, see: Bjorsvik et al. (2001 ▶); Cutroneo et al. (2007 ▶); Enzweiler et al. (2006 ▶).

Experimental

Crystal data

C10H9NO6

M = 239.18

Triclinic,

a = 4.0130 (8) Å

b = 10.660 (2) Å

c = 12.643 (3) Å

α = 106.11 (3)°

β = 93.74 (3)°

γ = 91.46 (3)°

V = 517.97 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 (2) K

0.40 × 0.05 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶)) T min = 0.950, T max = 0.994

2178 measured reflections

1885 independent reflections

1144 reflections with I > 2σ(I)

R int = 0.041

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.172

S = 1.01

1885 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024938/cs2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024938/cs2086Isup2.hkl

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

C10H9NO6	Z = 2
Mr = 239.18	F000 = 248
Triclinic, P1	Dx = 1.534 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 4.0130 (8) Å	Cell parameters from 25 reflections
b = 10.660 (2) Å	θ = 8–12º
c = 12.643 (3) Å	µ = 0.13 mm−1
α = 106.11 (3)º	T = 293 (2) K
β = 93.74 (3)º	Needle, colourless
γ = 91.46 (3)º	0.40 × 0.05 × 0.05 mm
V = 517.97 (18) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.041
Radiation source: fine-focus sealed tube	θmax = 25.3º
Monochromator: graphite	θmin = 1.7º
T = 293(2) K	h = −4→4
ω/2θ scans	k = −12→12
Absorption correction: ψ scan(North et al., 1968))	l = 0→15
Tmin = 0.950, Tmax = 0.994	3 standard reflections
2178 measured reflections	every 200 reflections
1885 independent reflections	intensity decay: none
1144 reflections with I > 2σ(I)

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)] = 0.073	H-atom parameters constrained
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.05P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1885 reflections	Δρmax = 0.28 e Å−3
154 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
N	0.5209 (9)	0.7040 (3)	0.8012 (3)	0.0572 (8)
O1	0.7307 (7)	0.1642 (2)	0.5059 (2)	0.0642 (8)
C1	0.8443 (12)	0.0907 (4)	0.4027 (3)	0.0717 (13)
H1A	0.8215	−0.0010	0.3965	0.108*
H1B	1.0748	0.1145	0.3992	0.108*
H1C	0.7126	0.1094	0.3431	0.108*
O2	0.8638 (9)	0.3487 (3)	0.4668 (2)	0.0825 (10)
C2	0.7532 (9)	0.2943 (3)	0.5284 (3)	0.0480 (9)
O3	0.2103 (7)	0.1601 (2)	0.8322 (2)	0.0608 (8)
C3	0.0691 (12)	0.0824 (4)	0.8961 (4)	0.0703 (12)
H3A	0.0833	−0.0086	0.8583	0.105*
H3B	−0.1610	0.1022	0.9054	0.105*
H3C	0.1906	0.1016	0.9671	0.105*
O4	0.1018 (8)	0.3426 (3)	0.9595 (2)	0.0739 (9)
C4	0.2108 (9)	0.2883 (3)	0.8735 (3)	0.0482 (9)
C5	0.3639 (8)	0.3588 (3)	0.8013 (3)	0.0424 (8)
O5	0.3683 (10)	0.7593 (3)	0.8783 (3)	0.0957 (12)
C6	0.3703 (9)	0.4947 (3)	0.8341 (3)	0.0465 (9)
H6A	0.2839	0.5401	0.8996	0.056*
O6	0.6840 (9)	0.7614 (3)	0.7524 (3)	0.0910 (11)
C7	0.5090 (8)	0.5598 (3)	0.7663 (3)	0.0445 (8)
C8	0.6352 (8)	0.4972 (3)	0.6687 (3)	0.0457 (8)
H8A	0.7276	0.5447	0.6254	0.055*
C9	0.6236 (9)	0.3612 (3)	0.6351 (3)	0.0448 (8)
C10	0.4871 (8)	0.2942 (3)	0.7022 (3)	0.0450 (8)
H10A	0.4781	0.2033	0.6802	0.054*

	U11	U22	U33	U12	U13	U23
N	0.065 (2)	0.0474 (18)	0.061 (2)	0.0053 (16)	0.0112 (17)	0.0155 (16)
O1	0.091 (2)	0.0508 (15)	0.0511 (15)	0.0022 (14)	0.0238 (14)	0.0100 (12)
C1	0.099 (4)	0.062 (2)	0.054 (2)	0.013 (2)	0.027 (2)	0.009 (2)
O2	0.124 (3)	0.0604 (17)	0.0677 (19)	−0.0108 (17)	0.0448 (18)	0.0181 (15)
C2	0.049 (2)	0.0464 (19)	0.050 (2)	−0.0043 (16)	0.0047 (17)	0.0156 (17)
O3	0.085 (2)	0.0465 (14)	0.0549 (16)	0.0031 (13)	0.0257 (14)	0.0166 (12)
C3	0.089 (3)	0.057 (2)	0.072 (3)	−0.002 (2)	0.027 (2)	0.025 (2)
O4	0.105 (2)	0.0593 (17)	0.0644 (18)	0.0145 (16)	0.0411 (17)	0.0209 (14)
C4	0.049 (2)	0.049 (2)	0.048 (2)	0.0061 (16)	0.0103 (17)	0.0131 (17)
C5	0.0417 (19)	0.0443 (18)	0.0420 (19)	0.0034 (15)	0.0021 (15)	0.0139 (15)
O5	0.134 (3)	0.0523 (17)	0.107 (3)	0.0219 (18)	0.057 (2)	0.0198 (17)
C6	0.050 (2)	0.0473 (19)	0.0437 (19)	0.0042 (16)	0.0029 (16)	0.0145 (16)
O6	0.131 (3)	0.0527 (17)	0.089 (2)	−0.0210 (18)	0.036 (2)	0.0148 (16)
C7	0.0388 (19)	0.0405 (17)	0.054 (2)	0.0001 (15)	−0.0011 (16)	0.0137 (16)
C8	0.045 (2)	0.0507 (19)	0.0432 (19)	−0.0005 (16)	0.0012 (16)	0.0174 (16)
C9	0.047 (2)	0.0464 (19)	0.0412 (18)	0.0013 (16)	0.0028 (16)	0.0127 (15)
C10	0.044 (2)	0.0449 (18)	0.046 (2)	−0.0032 (15)	0.0042 (16)	0.0130 (16)

N—O6	1.194 (4)	C3—H3B	0.9600
N—O5	1.204 (4)	C3—H3C	0.9600
N—C7	1.475 (4)	O4—C4	1.198 (4)
O1—C2	1.336 (4)	C4—C5	1.485 (5)
O1—C1	1.433 (4)	C5—C10	1.381 (4)
C1—H1A	0.9600	C5—C6	1.391 (5)
C1—H1B	0.9600	C6—C7	1.378 (5)
C1—H1C	0.9600	C6—H6A	0.9300
O2—C2	1.193 (4)	C7—C8	1.366 (5)
C2—C9	1.475 (5)	C8—C9	1.392 (5)
O3—C4	1.320 (4)	C8—H8A	0.9300
O3—C3	1.438 (4)	C9—C10	1.381 (5)
C3—H3A	0.9600	C10—H10A	0.9300
O6—N—O5	122.5 (3)	O4—C4—C5	123.3 (3)
O6—N—C7	118.6 (3)	O3—C4—C5	112.4 (3)
O5—N—C7	118.9 (3)	C10—C5—C6	119.7 (3)
C2—O1—C1	116.9 (3)	C10—C5—C4	122.3 (3)
O1—C1—H1A	109.5	C6—C5—C4	117.9 (3)
O1—C1—H1B	109.5	C7—C6—C5	117.8 (3)
H1A—C1—H1B	109.5	C7—C6—H6A	121.1
O1—C1—H1C	109.5	C5—C6—H6A	121.1
H1A—C1—H1C	109.5	C8—C7—C6	123.1 (3)
H1B—C1—H1C	109.5	C8—C7—N	118.7 (3)
O2—C2—O1	122.5 (3)	C6—C7—N	118.2 (3)
O2—C2—C9	124.5 (3)	C7—C8—C9	119.0 (3)
O1—C2—C9	112.9 (3)	C7—C8—H8A	120.5
C4—O3—C3	116.9 (3)	C9—C8—H8A	120.5
O3—C3—H3A	109.5	C10—C9—C8	118.7 (3)
O3—C3—H3B	109.5	C10—C9—C2	122.6 (3)
H3A—C3—H3B	109.5	C8—C9—C2	118.7 (3)
O3—C3—H3C	109.5	C5—C10—C9	121.6 (3)
H3A—C3—H3C	109.5	C5—C10—H10A	119.2
H3B—C3—H3C	109.5	C9—C10—H10A	119.2
O4—C4—O3	124.3 (3)
C1—O1—C2—O2	−0.4 (6)	O6—N—C7—C6	168.8 (4)
C1—O1—C2—C9	178.7 (3)	O5—N—C7—C6	−10.6 (5)
C3—O3—C4—O4	−0.1 (6)	C6—C7—C8—C9	0.2 (5)
C3—O3—C4—C5	179.7 (3)	N—C7—C8—C9	−179.7 (3)
O4—C4—C5—C10	−179.8 (4)	C7—C8—C9—C10	−0.6 (5)
O3—C4—C5—C10	0.4 (5)	C7—C8—C9—C2	178.6 (3)
O4—C4—C5—C6	−2.1 (5)	O2—C2—C9—C10	177.7 (4)
O3—C4—C5—C6	178.1 (3)	O1—C2—C9—C10	−1.4 (5)
C10—C5—C6—C7	−1.5 (5)	O2—C2—C9—C8	−1.4 (6)
C4—C5—C6—C7	−179.3 (3)	O1—C2—C9—C8	179.5 (3)
C5—C6—C7—C8	0.8 (5)	C6—C5—C10—C9	1.2 (5)
C5—C6—C7—N	−179.2 (3)	C4—C5—C10—C9	178.9 (3)
O6—N—C7—C8	−11.2 (5)	C8—C9—C10—C5	−0.1 (5)
O5—N—C7—C8	169.4 (4)	C2—C9—C10—C5	−179.3 (3)