organic compounds
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl methanesulfonate
aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com
The 7H11N3O5S, contains two independent molecules with virtually identical conformations. The imidazole rings of both molecules are essentially planar (r.m.s. deviations = 0.0019 and 0.0038 Å), with a dihedral angle 9.25 (19)° between them. The nitro groups are oriented at 4.5 (2) and 6.44 (13)° with respect to the imidazole rings. In the crystal, molecules are linked to form a three-dimensional framework by C—H⋯O and C—H⋯N hydrogen bonds.
of the title compound, CRelated literature
For the biological activity of metronidazole, see: Zeb, Malik et al. (2012). For related structures, see: Yousuf et al. (2012); Zeb, Yousuf et al. (2012).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; 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, PARST (Nardelli, 1995) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812034964/pv2579sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034964/pv2579Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034964/pv2579Isup3.cml
The title compound was synthesized by adding methane sulfonyl chloride (16 mmol) drop wise into an ice-cooled solution of metronidazole (10 mmol) and triethylamine (16 mmol) in dry dichloromethane (DCM) with continuous stirring. The reaction mixture was further stirred in the ice bath for 4 h. The separated thick material was filtered and washed with water (20 ml X 3) to obtain a cream coloured solid which was dissolved and recrystallized from DCM by slow evaporation to give pure crystals of the title compound (82% yield), suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma–Aldrich.
H atoms on methyl, methylene and methine were positioned geometrically with C—H = 0.96, 0.97 and 0.93 Å respectively, and constrained to ride on their parent atoms with Uiso(H)= 1.2Ueq(CH and CH2) and 1.5Ueq(CH3). A rotating group model was applied to the methyl groups.
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. Fig. 2. A view of the C—-H···O and C—H···N hydrogen bonds (dotted lines) in the of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. |
C7H11N3O5S | Z = 4 |
Mr = 249.26 | F(000) = 520 |
Triclinic, P1 | Dx = 1.573 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8547 (17) Å | Cell parameters from 3658 reflections |
b = 10.927 (2) Å | θ = 2.4–27.9° |
c = 12.033 (2) Å | µ = 0.32 mm−1 |
α = 112.702 (4)° | T = 273 K |
β = 100.614 (4)° | Plate, colorles |
γ = 90.052 (4)° | 0.40 × 0.21 × 0.08 mm |
V = 1052.4 (3) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 3918 independent reflections |
Radiation source: fine-focus sealed tube | 3078 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scan | θmax = 25.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→10 |
Tmin = 0.883, Tmax = 0.975 | k = −13→13 |
11649 measured reflections | l = −14→14 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0914P)2 + 0.2849P] where P = (Fo2 + 2Fc2)/3 |
3918 reflections | (Δ/σ)max < 0.001 |
291 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C7H11N3O5S | γ = 90.052 (4)° |
Mr = 249.26 | V = 1052.4 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.8547 (17) Å | Mo Kα radiation |
b = 10.927 (2) Å | µ = 0.32 mm−1 |
c = 12.033 (2) Å | T = 273 K |
α = 112.702 (4)° | 0.40 × 0.21 × 0.08 mm |
β = 100.614 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 3918 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 3078 reflections with I > 2σ(I) |
Tmin = 0.883, Tmax = 0.975 | Rint = 0.033 |
11649 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.79 e Å−3 |
3918 reflections | Δρmin = −0.32 e Å−3 |
291 parameters |
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 | ||
S1 | 0.09144 (8) | −0.18810 (7) | 0.47184 (7) | 0.0370 (2) | |
S2 | 0.60576 (8) | 0.68767 (7) | 0.52683 (7) | 0.0356 (2) | |
O1 | −0.2081 (3) | 0.3132 (3) | 0.8913 (3) | 0.0621 (7) | |
O2 | −0.1805 (3) | 0.1027 (2) | 0.8395 (2) | 0.0557 (6) | |
O3 | 0.1479 (2) | −0.1063 (2) | 0.61360 (19) | 0.0384 (5) | |
O4 | −0.0597 (2) | −0.1572 (2) | 0.4331 (2) | 0.0475 (6) | |
O5 | 0.2124 (3) | −0.1640 (2) | 0.4178 (2) | 0.0524 (6) | |
O6 | 0.0876 (2) | 0.1903 (2) | 0.1110 (2) | 0.0526 (6) | |
O7 | 0.1462 (2) | 0.4013 (2) | 0.1692 (2) | 0.0493 (6) | |
O8 | 0.5899 (2) | 0.60582 (19) | 0.38527 (18) | 0.0365 (5) | |
O9 | 0.7537 (2) | 0.6633 (2) | 0.5805 (2) | 0.0498 (6) | |
O10 | 0.4738 (2) | 0.6572 (2) | 0.5663 (2) | 0.0474 (6) | |
N1 | −0.1298 (3) | 0.2166 (3) | 0.8633 (2) | 0.0398 (6) | |
N2 | 0.1317 (2) | 0.1471 (2) | 0.8363 (2) | 0.0301 (5) | |
N3 | 0.2445 (3) | 0.3407 (2) | 0.8613 (2) | 0.0423 (6) | |
N4 | 0.1824 (3) | 0.2858 (2) | 0.1409 (2) | 0.0348 (6) | |
N5 | 0.4575 (2) | 0.3517 (2) | 0.1632 (2) | 0.0288 (5) | |
N7 | 0.5555 (3) | 0.1572 (2) | 0.1374 (3) | 0.0433 (6) | |
C1 | 0.4070 (4) | 0.1507 (4) | 0.8164 (3) | 0.0507 (8) | |
H1A | 0.4842 | 0.2158 | 0.8222 | 0.076* | |
H1B | 0.3896 | 0.0805 | 0.7359 | 0.076* | |
H1C | 0.4415 | 0.1144 | 0.8770 | 0.076* | |
C2 | 0.2630 (3) | 0.2136 (3) | 0.8381 (3) | 0.0348 (6) | |
C3 | 0.0965 (4) | 0.3589 (3) | 0.8737 (3) | 0.0405 (7) | |
H3B | 0.0509 | 0.4390 | 0.8902 | 0.049* | |
C4 | 0.0247 (3) | 0.2410 (3) | 0.8582 (3) | 0.0336 (6) | |
C5 | 0.1153 (3) | 0.0068 (3) | 0.8203 (3) | 0.0333 (6) | |
H5B | 0.0572 | 0.0000 | 0.8789 | 0.040* | |
H5C | 0.2167 | −0.0227 | 0.8384 | 0.040* | |
C6 | 0.0360 (3) | −0.0831 (3) | 0.6936 (3) | 0.0387 (7) | |
H6B | −0.0012 | −0.1667 | 0.6934 | 0.046* | |
H6C | −0.0513 | −0.0420 | 0.6649 | 0.046* | |
C7 | 0.0862 (4) | −0.3532 (3) | 0.4587 (4) | 0.0547 (9) | |
H7A | 0.0617 | −0.4118 | 0.3734 | 0.082* | |
H7B | 0.0090 | −0.3678 | 0.4997 | 0.082* | |
H7C | 0.1850 | −0.3704 | 0.4958 | 0.082* | |
C8 | 0.7433 (4) | 0.3470 (4) | 0.1814 (4) | 0.0540 (9) | |
H8A | 0.8153 | 0.2796 | 0.1668 | 0.081* | |
H8B | 0.7714 | 0.4106 | 0.2648 | 0.081* | |
H8C | 0.7449 | 0.3912 | 0.1264 | 0.081* | |
C9 | 0.5861 (3) | 0.2846 (3) | 0.1602 (3) | 0.0346 (6) | |
C10 | 0.4009 (3) | 0.1407 (3) | 0.1252 (3) | 0.0391 (7) | |
H10B | 0.3460 | 0.0609 | 0.1085 | 0.047* | |
C11 | 0.3377 (3) | 0.2588 (3) | 0.1412 (3) | 0.0317 (6) | |
C12 | 0.4499 (3) | 0.4921 (3) | 0.1791 (3) | 0.0317 (6) | |
H12A | 0.3617 | 0.4992 | 0.1214 | 0.038* | |
H12B | 0.5418 | 0.5208 | 0.1596 | 0.038* | |
C13 | 0.4371 (3) | 0.5828 (3) | 0.3059 (3) | 0.0362 (7) | |
H13A | 0.4006 | 0.6665 | 0.3060 | 0.043* | |
H13B | 0.3644 | 0.5427 | 0.3357 | 0.043* | |
C14 | 0.6070 (4) | 0.8524 (3) | 0.5396 (3) | 0.0522 (9) | |
H14A | 0.6396 | 0.9112 | 0.6243 | 0.078* | |
H14B | 0.5051 | 0.8703 | 0.5088 | 0.078* | |
H14C | 0.6769 | 0.8662 | 0.4925 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0370 (4) | 0.0336 (4) | 0.0394 (4) | 0.0035 (3) | 0.0099 (3) | 0.0123 (3) |
S2 | 0.0336 (4) | 0.0329 (4) | 0.0374 (4) | −0.0030 (3) | 0.0037 (3) | 0.0122 (3) |
O1 | 0.0480 (14) | 0.0549 (15) | 0.090 (2) | 0.0220 (12) | 0.0258 (13) | 0.0309 (14) |
O2 | 0.0407 (12) | 0.0415 (13) | 0.0877 (19) | −0.0049 (10) | 0.0170 (12) | 0.0266 (13) |
O3 | 0.0320 (10) | 0.0386 (11) | 0.0433 (12) | 0.0017 (8) | 0.0092 (9) | 0.0139 (9) |
O4 | 0.0437 (12) | 0.0484 (13) | 0.0458 (13) | 0.0075 (10) | 0.0032 (10) | 0.0161 (11) |
O5 | 0.0546 (14) | 0.0558 (15) | 0.0531 (14) | 0.0045 (11) | 0.0236 (11) | 0.0224 (12) |
O6 | 0.0369 (12) | 0.0487 (14) | 0.0702 (16) | −0.0152 (10) | 0.0100 (11) | 0.0215 (12) |
O7 | 0.0376 (12) | 0.0411 (13) | 0.0683 (16) | 0.0083 (9) | 0.0096 (10) | 0.0207 (11) |
O8 | 0.0283 (10) | 0.0365 (11) | 0.0409 (12) | −0.0017 (8) | 0.0047 (8) | 0.0120 (9) |
O9 | 0.0403 (12) | 0.0544 (14) | 0.0508 (14) | −0.0003 (10) | −0.0048 (10) | 0.0227 (11) |
O10 | 0.0472 (13) | 0.0512 (14) | 0.0444 (13) | −0.0052 (10) | 0.0135 (10) | 0.0176 (11) |
N1 | 0.0328 (13) | 0.0408 (15) | 0.0479 (16) | 0.0019 (11) | 0.0074 (11) | 0.0198 (12) |
N2 | 0.0279 (11) | 0.0279 (12) | 0.0355 (13) | −0.0002 (9) | 0.0049 (9) | 0.0142 (10) |
N3 | 0.0403 (14) | 0.0342 (14) | 0.0523 (16) | −0.0069 (11) | 0.0075 (12) | 0.0176 (12) |
N4 | 0.0332 (13) | 0.0364 (14) | 0.0360 (14) | −0.0010 (10) | 0.0057 (10) | 0.0160 (11) |
N5 | 0.0296 (12) | 0.0243 (11) | 0.0321 (12) | 0.0001 (9) | 0.0057 (9) | 0.0110 (10) |
N7 | 0.0451 (15) | 0.0314 (14) | 0.0537 (17) | 0.0077 (11) | 0.0133 (12) | 0.0154 (12) |
C1 | 0.0341 (16) | 0.056 (2) | 0.069 (2) | 0.0004 (14) | 0.0132 (15) | 0.0303 (19) |
C2 | 0.0329 (15) | 0.0343 (16) | 0.0379 (17) | −0.0080 (12) | 0.0025 (12) | 0.0170 (13) |
C3 | 0.0459 (17) | 0.0277 (15) | 0.0475 (19) | 0.0011 (12) | 0.0069 (14) | 0.0156 (14) |
C4 | 0.0315 (14) | 0.0328 (15) | 0.0365 (16) | 0.0010 (11) | 0.0078 (12) | 0.0132 (13) |
C5 | 0.0347 (15) | 0.0281 (14) | 0.0389 (16) | −0.0020 (11) | 0.0060 (12) | 0.0157 (12) |
C6 | 0.0365 (15) | 0.0334 (16) | 0.0438 (18) | −0.0042 (12) | 0.0113 (13) | 0.0113 (13) |
C7 | 0.052 (2) | 0.0371 (18) | 0.081 (3) | 0.0074 (15) | 0.0218 (18) | 0.0253 (18) |
C8 | 0.0326 (17) | 0.055 (2) | 0.077 (3) | 0.0052 (15) | 0.0153 (16) | 0.0269 (19) |
C9 | 0.0335 (15) | 0.0315 (15) | 0.0407 (17) | 0.0053 (11) | 0.0124 (12) | 0.0141 (13) |
C10 | 0.0417 (17) | 0.0291 (15) | 0.0478 (18) | −0.0017 (12) | 0.0116 (13) | 0.0153 (14) |
C11 | 0.0320 (14) | 0.0289 (14) | 0.0347 (15) | −0.0008 (11) | 0.0066 (11) | 0.0129 (12) |
C12 | 0.0327 (14) | 0.0253 (13) | 0.0386 (16) | −0.0001 (11) | 0.0055 (12) | 0.0148 (12) |
C13 | 0.0318 (14) | 0.0305 (15) | 0.0418 (17) | 0.0038 (11) | 0.0030 (12) | 0.0112 (13) |
C14 | 0.0438 (18) | 0.0342 (17) | 0.076 (3) | −0.0022 (14) | 0.0064 (17) | 0.0221 (17) |
S1—O4 | 1.420 (2) | C1—H1A | 0.9600 |
S1—O5 | 1.425 (2) | C1—H1B | 0.9600 |
S1—O3 | 1.571 (2) | C1—H1C | 0.9600 |
S1—C7 | 1.749 (3) | C3—C4 | 1.367 (4) |
S2—O9 | 1.423 (2) | C3—H3B | 0.9300 |
S2—O10 | 1.424 (2) | C5—C6 | 1.494 (4) |
S2—O8 | 1.567 (2) | C5—H5B | 0.9700 |
S2—C14 | 1.746 (3) | C5—H5C | 0.9700 |
O1—N1 | 1.234 (3) | C6—H6B | 0.9700 |
O2—N1 | 1.228 (3) | C6—H6C | 0.9700 |
O3—C6 | 1.461 (3) | C7—H7A | 0.9600 |
O6—N4 | 1.233 (3) | C7—H7B | 0.9600 |
O7—N4 | 1.233 (3) | C7—H7C | 0.9600 |
O8—C13 | 1.464 (3) | C8—C9 | 1.484 (4) |
N1—C4 | 1.410 (4) | C8—H8A | 0.9600 |
N2—C2 | 1.363 (3) | C8—H8B | 0.9600 |
N2—C4 | 1.381 (4) | C8—H8C | 0.9600 |
N2—C5 | 1.473 (3) | C10—C11 | 1.366 (4) |
N3—C2 | 1.323 (4) | C10—H10B | 0.9300 |
N3—C3 | 1.352 (4) | C12—C13 | 1.490 (4) |
N4—C11 | 1.406 (3) | C12—H12A | 0.9700 |
N5—C9 | 1.353 (3) | C12—H12B | 0.9700 |
N5—C11 | 1.383 (3) | C13—H13A | 0.9700 |
N5—C12 | 1.474 (3) | C13—H13B | 0.9700 |
N7—C9 | 1.328 (4) | C14—H14A | 0.9600 |
N7—C10 | 1.354 (4) | C14—H14B | 0.9600 |
C1—C2 | 1.467 (4) | C14—H14C | 0.9600 |
O4—S1—O5 | 118.95 (14) | C6—C5—H5C | 109.0 |
O4—S1—O3 | 109.90 (12) | H5B—C5—H5C | 107.8 |
O5—S1—O3 | 104.65 (13) | O3—C6—C5 | 107.7 (2) |
O4—S1—C7 | 109.32 (15) | O3—C6—H6B | 110.2 |
O5—S1—C7 | 109.50 (15) | C5—C6—H6B | 110.2 |
O3—S1—C7 | 103.32 (15) | O3—C6—H6C | 110.2 |
O9—S2—O10 | 118.88 (14) | C5—C6—H6C | 110.2 |
O9—S2—O8 | 104.78 (13) | H6B—C6—H6C | 108.5 |
O10—S2—O8 | 109.83 (12) | S1—C7—H7A | 109.5 |
O9—S2—C14 | 109.74 (15) | S1—C7—H7B | 109.5 |
O10—S2—C14 | 109.15 (15) | H7A—C7—H7B | 109.5 |
O8—S2—C14 | 103.28 (15) | S1—C7—H7C | 109.5 |
C6—O3—S1 | 118.58 (18) | H7A—C7—H7C | 109.5 |
C13—O8—S2 | 118.53 (17) | H7B—C7—H7C | 109.5 |
O2—N1—O1 | 123.1 (3) | C9—C8—H8A | 109.5 |
O2—N1—C4 | 119.8 (2) | C9—C8—H8B | 109.5 |
O1—N1—C4 | 117.1 (3) | H8A—C8—H8B | 109.5 |
C2—N2—C4 | 104.9 (2) | C9—C8—H8C | 109.5 |
C2—N2—C5 | 125.9 (2) | H8A—C8—H8C | 109.5 |
C4—N2—C5 | 129.1 (2) | H8B—C8—H8C | 109.5 |
C2—N3—C3 | 106.4 (2) | N7—C9—N5 | 112.3 (2) |
O7—N4—O6 | 122.9 (2) | N7—C9—C8 | 124.0 (3) |
O7—N4—C11 | 119.9 (2) | N5—C9—C8 | 123.7 (3) |
O6—N4—C11 | 117.3 (2) | N7—C10—C11 | 109.8 (3) |
C9—N5—C11 | 105.3 (2) | N7—C10—H10B | 125.1 |
C9—N5—C12 | 126.1 (2) | C11—C10—H10B | 125.1 |
C11—N5—C12 | 128.5 (2) | C10—C11—N5 | 106.9 (2) |
C9—N7—C10 | 105.7 (2) | C10—C11—N4 | 127.9 (3) |
C2—C1—H1A | 109.5 | N5—C11—N4 | 125.1 (2) |
C2—C1—H1B | 109.5 | N5—C12—C13 | 113.3 (2) |
H1A—C1—H1B | 109.5 | N5—C12—H12A | 108.9 |
C2—C1—H1C | 109.5 | C13—C12—H12A | 108.9 |
H1A—C1—H1C | 109.5 | N5—C12—H12B | 108.9 |
H1B—C1—H1C | 109.5 | C13—C12—H12B | 108.9 |
N3—C2—N2 | 112.0 (3) | H12A—C12—H12B | 107.7 |
N3—C2—C1 | 124.5 (3) | O8—C13—C12 | 108.1 (2) |
N2—C2—C1 | 123.6 (3) | O8—C13—H13A | 110.1 |
N3—C3—C4 | 109.2 (3) | C12—C13—H13A | 110.1 |
N3—C3—H3B | 125.4 | O8—C13—H13B | 110.1 |
C4—C3—H3B | 125.4 | C12—C13—H13B | 110.1 |
C3—C4—N2 | 107.5 (2) | H13A—C13—H13B | 108.4 |
C3—C4—N1 | 127.4 (3) | S2—C14—H14A | 109.5 |
N2—C4—N1 | 125.1 (2) | S2—C14—H14B | 109.5 |
N2—C5—C6 | 113.0 (2) | H14A—C14—H14B | 109.5 |
N2—C5—H5B | 109.0 | S2—C14—H14C | 109.5 |
C6—C5—H5B | 109.0 | H14A—C14—H14C | 109.5 |
N2—C5—H5C | 109.0 | H14B—C14—H14C | 109.5 |
O4—S1—O3—C6 | 36.6 (2) | C4—N2—C5—C6 | 80.8 (3) |
O5—S1—O3—C6 | 165.4 (2) | S1—O3—C6—C5 | −174.80 (18) |
C7—S1—O3—C6 | −79.9 (2) | N2—C5—C6—O3 | 77.7 (3) |
O9—S2—O8—C13 | 165.3 (2) | C10—N7—C9—N5 | −0.1 (3) |
O10—S2—O8—C13 | 36.5 (2) | C10—N7—C9—C8 | 179.2 (3) |
C14—S2—O8—C13 | −79.8 (2) | C11—N5—C9—N7 | 0.4 (3) |
C3—N3—C2—N2 | −0.8 (3) | C12—N5—C9—N7 | −176.3 (3) |
C3—N3—C2—C1 | 179.1 (3) | C11—N5—C9—C8 | −179.0 (3) |
C4—N2—C2—N3 | 1.0 (3) | C12—N5—C9—C8 | 4.4 (5) |
C5—N2—C2—N3 | −176.3 (3) | C9—N7—C10—C11 | −0.2 (3) |
C4—N2—C2—C1 | −178.8 (3) | N7—C10—C11—N5 | 0.4 (3) |
C5—N2—C2—C1 | 3.9 (4) | N7—C10—C11—N4 | −177.2 (3) |
C2—N3—C3—C4 | 0.2 (3) | C9—N5—C11—C10 | −0.5 (3) |
N3—C3—C4—N2 | 0.4 (3) | C12—N5—C11—C10 | 176.1 (3) |
N3—C3—C4—N1 | −179.7 (3) | C9—N5—C11—N4 | 177.3 (3) |
C2—N2—C4—C3 | −0.9 (3) | C12—N5—C11—N4 | −6.1 (4) |
C5—N2—C4—C3 | 176.3 (3) | O7—N4—C11—C10 | 172.6 (3) |
C2—N2—C4—N1 | 179.3 (3) | O6—N4—C11—C10 | −7.8 (4) |
C5—N2—C4—N1 | −3.5 (5) | O7—N4—C11—N5 | −4.7 (4) |
O2—N1—C4—C3 | 175.3 (3) | O6—N4—C11—N5 | 174.9 (3) |
O1—N1—C4—C3 | −4.2 (5) | C9—N5—C12—C13 | −102.3 (3) |
O2—N1—C4—N2 | −4.9 (4) | C11—N5—C12—C13 | 81.8 (3) |
O1—N1—C4—N2 | 175.7 (3) | S2—O8—C13—C12 | −174.36 (17) |
C2—N2—C5—C6 | −102.5 (3) | N5—C12—C13—O8 | 77.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O6i | 0.97 | 2.50 | 3.235 (4) | 133 |
C5—H5C···N7ii | 0.97 | 2.54 | 3.484 (4) | 165 |
C7—H7B···O9iii | 0.96 | 2.59 | 3.498 (4) | 157 |
C7—H7C···O10iv | 0.96 | 2.52 | 3.423 (4) | 157 |
C12—H12A···O1v | 0.97 | 2.50 | 3.250 (5) | 134 |
C12—H12B···N3vi | 0.97 | 2.53 | 3.472 (4) | 164 |
C14—H14B···O5vii | 0.96 | 2.59 | 3.507 (4) | 160 |
C14—H14C···O4viii | 0.96 | 2.55 | 3.414 (4) | 150 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1, y−1, z; (iv) x, y−1, z; (v) −x, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (vii) x, y+1, z; (viii) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C7H11N3O5S |
Mr | 249.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 8.8547 (17), 10.927 (2), 12.033 (2) |
α, β, γ (°) | 112.702 (4), 100.614 (4), 90.052 (4) |
V (Å3) | 1052.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.40 × 0.21 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.883, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11649, 3918, 3078 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.152, 1.07 |
No. of reflections | 3918 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.79, −0.32 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O6i | 0.9700 | 2.5000 | 3.235 (4) | 133.00 |
C5—H5C···N7ii | 0.9700 | 2.5400 | 3.484 (4) | 165.00 |
C7—H7B···O9iii | 0.9600 | 2.5900 | 3.498 (4) | 157.00 |
C7—H7C···O10iv | 0.9600 | 2.5200 | 3.423 (4) | 157.00 |
C12—H12A···O1v | 0.9700 | 2.5000 | 3.250 (5) | 134.00 |
C12—H12B···N3vi | 0.9700 | 2.5300 | 3.472 (4) | 164.00 |
C14—H14B···O5vii | 0.9600 | 2.5900 | 3.507 (4) | 160.00 |
C14—H14C···O4viii | 0.9600 | 2.5500 | 3.414 (4) | 150.00 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1, y−1, z; (iv) x, y−1, z; (v) −x, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (vii) x, y+1, z; (viii) x+1, y+1, z. |
Footnotes
‡Additional correspondence author, e-mail: bashafz@gmail.com.
References
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yousuf, S., Zeb, A. & Basha, F. Z. (2012). Acta Cryst. E68, o952. CSD CrossRef IUCr Journals Google Scholar
Zeb, A., Malik, I., Rasheed, S., Choudhary, M. I. & Basha, F. Z. (2012). Med. Chem. 8, 846–852. CrossRef CAS PubMed Google Scholar
Zeb, A., Yousuf, S. & Basha, F. Z. (2012). Acta Cryst. E68, o1218. CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Metronidazole (Flagyl) is a well known broad spectrum antibiotic. The structural analogues of metronidazole are reported to have a wide range of biological activities including antibacterial anticancer, antiglycation and H. pylori urease inhibitors (Zeb, Malik et al., 2012). The title compound is a methanesulfonate derivative of metronidazole, synthesized as a part of our ongoing reaserch to synthesize and evaluate the antiglycation potential and establish structure activity relationship of the structural analogues of metronidazole.
The title compound contains two independent molecules in an asymmetric unit (Fig. 1) with identical conformations. The two imidazole rings (C2—C4/N2/N3 and C9—C11/N5/N7) are individually planar with r.m.s.d's 0.0038 and 0.0019 Å, respectively; the dihedral angle between the mean planes of the imidazole rings is 9.25 (19)°. The nitro groups N1/O1/O2 and N4/O6/O7 are oriented at 4.5 (2) and 6.44 (13)° with respect to the imidazole rings (C2—C4/N2/N3) and (C9—C11/N5/N7), respectively. The bond distances and angles in both molecules of the title compound agree very well with the corresponding bond distances and angles reported in closely related compounds (Yousuf et al., 2012; Zeb et al., 2012). The crystal packing (Fig. 2) is consolidated by weak intermolecular C—H···O and C—H···N type hydrogen bonds (Table 1).