organic compounds
2-Nitrobenzyl methanesulfonate
aDepartment of Physics, Dr M. G. R. Educational and Research Institute, Maduravoyal, Chennai, India, bDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Chemistry, BET Academy of Higher Education, Bharathi College, Bharthi Nagara, Mandya 571 422, India
*Correspondence e-mail: nagendra088@yahoo.co.in
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, molecules are linked by C—H⋯O hydrogen bonds, generating a three-dimensional network.
CCDC reference: 998614
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
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Data collection: APEX2 (Bruker, 2013); cell 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.
Supporting information
CCDC reference: 998614
10.1107/S160053681400899X/hb7217sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400899X/hb7217Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400899X/hb7217Isup3.cml
The hydrogen atom were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) =1.5Ueq(C-methyl) and = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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 (Sheldrick, 2008).Fig. 1. A view of the title molecule, with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. A viewed along the b axis of the crystal packing of the title compound. |
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) |
C8H9NO5S | V = 1006.5 (5) Å3 |
Mr = 231.23 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 12.414 (3) Å | µ = 2.94 mm−1 |
b = 7.967 (2) Å | T = 296 K |
c = 10.994 (3) Å | 0.23 × 0.22 × 0.21 mm |
β = 112.235 (11)° |
Bruker X8 Proteum CCD diffractometer | 1663 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 1541 reflections with I > 2σ(I) |
Tmin = 0.552, Tmax = 0.578 | Rint = 0.047 |
6524 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.41 e Å−3 |
1663 reflections | Δρmin = −0.32 e Å−3 |
138 parameters |
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 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) x, −y+1/2, z+1/2. |
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 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) x, −y+1/2, z+1/2. |
Acknowledgements
We are grateful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. PN thanks the BET Academy of Higher Education for research facilities.
References
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Nitroalkenes have been used as substrates for Michael addition reactions (Ranu & Banerjee, 2005) and for the synthesis of many organic molecules (Ballini et al., 2005).
The ORTEP of the title molecule is shown in figure 1. The molecules in the crystal structure are connected with C—H···O hydrogen bonds (Table 1). The C8—H8B···O4 hydrogen bond exhibits ring motifs of the type R22(8). The overall geometry of the title compound is similar to the 3,5-dinitrobenzyl methanesulfonate (Khan et al., 2008). Overall packing of the molecule is shown in figure 2.