2-Nitro-benzyl methane-sulfonate.

In the title compound, C8H9NO5S, the dihedral angle between the benzene ring and the nitro group is 5.86 (15)° and the C-C-O-S group adopts an anti conformation [torsion angle = -168.44 (15)°]. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For background to nitro­benzene derivatives, see: Ranu & Banerjee (2005 ▶); Ballini et al. (2005 ▶). For a related structure, see: Khan et al. (2008 ▶).

Experimental

Crystal data

C8H9NO5S

M = 231.23

Monoclinic,

a = 12.414 (3) Å

b = 7.967 (2) Å

c = 10.994 (3) Å

β = 112.235 (11)°

V = 1006.5 (5) Å3

Z = 4

Cu Kα radiation

μ = 2.94 mm−1

T = 296 K

0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.552, T max = 0.578

6524 measured reflections

1663 independent reflections

1541 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.112

S = 1.08

1663 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400899X/hb7217sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400899X/hb7217Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400899X/hb7217Isup3.cml

CCDC reference: 998614

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

C8H9NO5S	F(000) = 480
Mr = 231.23	Dx = 1.526 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1663 reflections
a = 12.414 (3) Å	θ = 3.8–64.5°
b = 7.967 (2) Å	µ = 2.94 mm−1
c = 10.994 (3) Å	T = 296 K
β = 112.235 (11)°	Block, red
V = 1006.5 (5) Å3	0.23 × 0.22 × 0.21 mm
Z = 4

Bruker X8 Proteum CCD diffractometer	1663 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1541 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.047
Detector resolution: 10.7 pixels mm-1	θmax = 64.5°, θmin = 3.9°
φ and ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −8→9
Tmin = 0.552, Tmax = 0.578	l = −12→9
6524 measured reflections

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0554P)2 + 0.5912P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1663 reflections	Δρmax = 0.41 e Å−3
138 parameters	Δρmin = −0.32 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: 0.0114 (9)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1	0.08637 (5)	0.25179 (7)	0.06271 (5)	0.0405 (2)
O1	0.43500 (18)	0.3906 (3)	0.69206 (16)	0.0672 (7)
O2	0.36003 (19)	0.2381 (2)	0.52088 (19)	0.0601 (7)
O3	0.16548 (14)	0.3941 (2)	0.15092 (14)	0.0458 (5)
O4	0.05351 (17)	0.3133 (3)	−0.06740 (15)	0.0592 (7)
O5	0.14617 (16)	0.0958 (2)	0.09607 (18)	0.0584 (6)
N1	0.38559 (15)	0.3744 (2)	0.57357 (17)	0.0376 (6)
C1	0.35397 (16)	0.5255 (2)	0.49184 (19)	0.0295 (6)
C2	0.3940 (2)	0.6755 (3)	0.5560 (2)	0.0411 (7)
C3	0.3686 (2)	0.8231 (3)	0.4862 (3)	0.0523 (9)
C4	0.3040 (2)	0.8185 (3)	0.3534 (3)	0.0533 (9)
C5	0.2634 (2)	0.6678 (3)	0.2901 (2)	0.0424 (7)
C6	0.28708 (17)	0.5157 (3)	0.35717 (19)	0.0310 (6)
C7	0.2405 (2)	0.3532 (3)	0.2870 (2)	0.0387 (7)
C8	−0.0341 (2)	0.2504 (3)	0.1059 (3)	0.0526 (9)
H2	0.43780	0.67660	0.64580	0.0490*
H3	0.39490	0.92490	0.52830	0.0630*
H4	0.28730	0.91790	0.30560	0.0640*
H5	0.21920	0.66820	0.20030	0.0510*
H7A	0.30420	0.28170	0.28830	0.0460*
H7B	0.19630	0.29430	0.32990	0.0460*
H8A	−0.01050	0.22110	0.19700	0.0790*
H8B	−0.08950	0.16960	0.05320	0.0790*
H8C	−0.06920	0.35980	0.09150	0.0790*

	U11	U22	U33	U12	U13	U23
S1	0.0457 (4)	0.0446 (4)	0.0265 (3)	−0.0009 (2)	0.0083 (3)	−0.0091 (2)
O1	0.0821 (13)	0.0607 (13)	0.0332 (10)	0.0016 (10)	−0.0071 (9)	0.0119 (8)
O2	0.0803 (13)	0.0282 (9)	0.0564 (12)	0.0036 (8)	0.0083 (10)	0.0025 (7)
O3	0.0555 (10)	0.0432 (9)	0.0289 (8)	−0.0069 (7)	0.0050 (7)	−0.0037 (7)
O4	0.0670 (11)	0.0806 (14)	0.0262 (9)	−0.0037 (10)	0.0134 (8)	−0.0061 (8)
O5	0.0595 (11)	0.0463 (11)	0.0559 (11)	0.0051 (8)	0.0065 (9)	−0.0161 (8)
N1	0.0376 (9)	0.0337 (10)	0.0345 (10)	0.0023 (7)	0.0056 (8)	0.0053 (8)
C1	0.0322 (10)	0.0256 (10)	0.0298 (10)	0.0008 (8)	0.0106 (8)	0.0013 (8)
C2	0.0463 (12)	0.0365 (12)	0.0349 (12)	−0.0059 (10)	0.0090 (10)	−0.0070 (9)
C3	0.0668 (16)	0.0272 (12)	0.0591 (16)	−0.0085 (11)	0.0197 (13)	−0.0070 (11)
C4	0.0712 (16)	0.0295 (12)	0.0571 (16)	−0.0019 (11)	0.0220 (13)	0.0121 (11)
C5	0.0531 (13)	0.0382 (13)	0.0325 (11)	−0.0006 (10)	0.0123 (10)	0.0058 (9)
C6	0.0339 (10)	0.0299 (11)	0.0303 (10)	−0.0002 (8)	0.0135 (9)	−0.0014 (8)
C7	0.0465 (12)	0.0361 (12)	0.0279 (11)	−0.0004 (9)	0.0079 (9)	−0.0034 (8)
C8	0.0529 (15)	0.0635 (18)	0.0402 (14)	−0.0060 (11)	0.0163 (12)	−0.0060 (11)

S1—O3	1.5715 (17)	C4—C5	1.384 (3)
S1—O4	1.4181 (18)	C5—C6	1.391 (3)
S1—O5	1.4227 (18)	C6—C7	1.506 (3)
S1—C8	1.732 (3)	C2—H2	0.9300
O1—N1	1.219 (2)	C3—H3	0.9300
O2—N1	1.215 (2)	C4—H4	0.9300
O3—C7	1.469 (3)	C5—H5	0.9300
N1—C1	1.464 (2)	C7—H7A	0.9700
C1—C2	1.381 (3)	C7—H7B	0.9700
C1—C6	1.399 (3)	C8—H8A	0.9600
C2—C3	1.374 (3)	C8—H8B	0.9600
C3—C4	1.375 (4)	C8—H8C	0.9600
O3—S1—O4	104.31 (11)	O3—C7—C6	107.68 (18)
O3—S1—O5	109.14 (10)	C1—C2—H2	120.00
O3—S1—C8	103.78 (11)	C3—C2—H2	120.00
O4—S1—O5	119.00 (13)	C2—C3—H3	120.00
O4—S1—C8	109.28 (14)	C4—C3—H3	120.00
O5—S1—C8	110.13 (12)	C3—C4—H4	120.00
S1—O3—C7	118.41 (14)	C5—C4—H4	120.00
O1—N1—O2	122.6 (2)	C4—C5—H5	119.00
O1—N1—C1	118.59 (18)	C6—C5—H5	119.00
O2—N1—C1	118.77 (17)	O3—C7—H7A	110.00
N1—C1—C2	115.91 (17)	O3—C7—H7B	110.00
N1—C1—C6	121.17 (17)	C6—C7—H7A	110.00
C2—C1—C6	122.93 (18)	C6—C7—H7B	110.00
C1—C2—C3	119.6 (2)	H7A—C7—H7B	108.00
C2—C3—C4	119.3 (2)	S1—C8—H8A	109.00
C3—C4—C5	120.8 (2)	S1—C8—H8B	110.00
C4—C5—C6	121.7 (2)	S1—C8—H8C	110.00
C1—C6—C5	115.73 (19)	H8A—C8—H8B	109.00
C1—C6—C7	123.31 (19)	H8A—C8—H8C	109.00
C5—C6—C7	120.95 (18)	H8B—C8—H8C	109.00
O4—S1—O3—C7	−163.22 (18)	C2—C1—C6—C5	0.5 (3)
O5—S1—O3—C7	−35.1 (2)	C2—C1—C6—C7	−178.4 (2)
C8—S1—O3—C7	82.36 (19)	N1—C1—C6—C7	1.5 (3)
S1—O3—C7—C6	−168.44 (15)	C1—C2—C3—C4	−0.2 (4)
O1—N1—C1—C2	6.4 (3)	C2—C3—C4—C5	0.8 (4)
O2—N1—C1—C2	−174.7 (2)	C3—C4—C5—C6	−0.7 (4)
O2—N1—C1—C6	5.4 (3)	C4—C5—C6—C1	0.1 (4)
O1—N1—C1—C6	−173.6 (2)	C4—C5—C6—C7	179.0 (2)
C6—C1—C2—C3	−0.4 (4)	C1—C6—C7—O3	174.4 (2)
N1—C1—C6—C5	−179.6 (2)	C5—C6—C7—O3	−4.4 (3)
N1—C1—C2—C3	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.54	3.266 (3)	135
C3—H3···O2ii	0.93	2.53	3.335 (3)	145
C7—H7B···O4iii	0.97	2.58	3.539 (3)	169
C8—H8A···O4iii	0.96	2.42	3.374 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.54	3.266 (3)	135
C3—H3⋯O2ii	0.93	2.53	3.335 (3)	145
C7—H7B⋯O4iii	0.97	2.58	3.539 (3)	169
C8—H8A⋯O4iii	0.96	2.42	3.374 (4)	172

Symmetry codes: (i) ; (ii) ; (iii) .