organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 6 August 2012; accepted 8 August 2012; online 25 August 2012)

The asymmetric unit of the title compound, C7H11N3O5S, 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.

Related literature

For the biological activity of metronidazole, see: Zeb, Malik et al. (2012[Zeb, A., Malik, I., Rasheed, S., Choudhary, M. I. & Basha, F. Z. (2012). Med. Chem. 8, 846-852.]). For related structures, see: Yousuf et al. (2012[Yousuf, S., Zeb, A. & Basha, F. Z. (2012). Acta Cryst. E68, o952.]); Zeb, Yousuf et al. (2012[Zeb, A., Yousuf, S. & Basha, F. Z. (2012). Acta Cryst. E68, o1218.]).

[Scheme 1]

Experimental

Crystal data
  • C7H11N3O5S

  • Mr = 249.26

  • Triclinic, [P \overline 1]

  • a = 8.8547 (17) Å

  • b = 10.927 (2) Å

  • c = 12.033 (2) Å

  • α = 112.702 (4)°

  • β = 100.614 (4)°

  • γ = 90.052 (4)°

  • V = 1052.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 273 K

  • 0.40 × 0.21 × 0.08 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.883, Tmax = 0.975

  • 11649 measured reflections

  • 3918 independent reflections

  • 3078 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.152

  • S = 1.07

  • 3918 reflections

  • 291 parameters

  • H-atom parameters constrained

  • Δρmax = 0.79 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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).

Related literature top

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 top

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.

Refinement top

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.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: 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).

Figures top
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 crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl methanesulfonate top
Crystal data top
C7H11N3O5SZ = 4
Mr = 249.26F(000) = 520
Triclinic, P1Dx = 1.573 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8547 (17) ÅCell parameters from 3658 reflections
b = 10.927 (2) Åθ = 2.4–27.9°
c = 12.033 (2) ŵ = 0.32 mm1
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
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3918 independent reflections
Radiation source: fine-focus sealed tube3078 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scanθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.883, Tmax = 0.975k = 1313
11649 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-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 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C7H11N3O5Sγ = 90.052 (4)°
Mr = 249.26V = 1052.4 (3) Å3
Triclinic, P1Z = 4
a = 8.8547 (17) ÅMo Kα radiation
b = 10.927 (2) ŵ = 0.32 mm1
c = 12.033 (2) ÅT = 273 K
α = 112.702 (4)°0.40 × 0.21 × 0.08 mm
β = 100.614 (4)°
Data collection top
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 = 0.975Rint = 0.033
11649 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.07Δρmax = 0.79 e Å3
3918 reflectionsΔρmin = 0.32 e Å3
291 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.09144 (8)0.18810 (7)0.47184 (7)0.0370 (2)
S20.60576 (8)0.68767 (7)0.52683 (7)0.0356 (2)
O10.2081 (3)0.3132 (3)0.8913 (3)0.0621 (7)
O20.1805 (3)0.1027 (2)0.8395 (2)0.0557 (6)
O30.1479 (2)0.1063 (2)0.61360 (19)0.0384 (5)
O40.0597 (2)0.1572 (2)0.4331 (2)0.0475 (6)
O50.2124 (3)0.1640 (2)0.4178 (2)0.0524 (6)
O60.0876 (2)0.1903 (2)0.1110 (2)0.0526 (6)
O70.1462 (2)0.4013 (2)0.1692 (2)0.0493 (6)
O80.5899 (2)0.60582 (19)0.38527 (18)0.0365 (5)
O90.7537 (2)0.6633 (2)0.5805 (2)0.0498 (6)
O100.4738 (2)0.6572 (2)0.5663 (2)0.0474 (6)
N10.1298 (3)0.2166 (3)0.8633 (2)0.0398 (6)
N20.1317 (2)0.1471 (2)0.8363 (2)0.0301 (5)
N30.2445 (3)0.3407 (2)0.8613 (2)0.0423 (6)
N40.1824 (3)0.2858 (2)0.1409 (2)0.0348 (6)
N50.4575 (2)0.3517 (2)0.1632 (2)0.0288 (5)
N70.5555 (3)0.1572 (2)0.1374 (3)0.0433 (6)
C10.4070 (4)0.1507 (4)0.8164 (3)0.0507 (8)
H1A0.48420.21580.82220.076*
H1B0.38960.08050.73590.076*
H1C0.44150.11440.87700.076*
C20.2630 (3)0.2136 (3)0.8381 (3)0.0348 (6)
C30.0965 (4)0.3589 (3)0.8737 (3)0.0405 (7)
H3B0.05090.43900.89020.049*
C40.0247 (3)0.2410 (3)0.8582 (3)0.0336 (6)
C50.1153 (3)0.0068 (3)0.8203 (3)0.0333 (6)
H5B0.05720.00000.87890.040*
H5C0.21670.02270.83840.040*
C60.0360 (3)0.0831 (3)0.6936 (3)0.0387 (7)
H6B0.00120.16670.69340.046*
H6C0.05130.04200.66490.046*
C70.0862 (4)0.3532 (3)0.4587 (4)0.0547 (9)
H7A0.06170.41180.37340.082*
H7B0.00900.36780.49970.082*
H7C0.18500.37040.49580.082*
C80.7433 (4)0.3470 (4)0.1814 (4)0.0540 (9)
H8A0.81530.27960.16680.081*
H8B0.77140.41060.26480.081*
H8C0.74490.39120.12640.081*
C90.5861 (3)0.2846 (3)0.1602 (3)0.0346 (6)
C100.4009 (3)0.1407 (3)0.1252 (3)0.0391 (7)
H10B0.34600.06090.10850.047*
C110.3377 (3)0.2588 (3)0.1412 (3)0.0317 (6)
C120.4499 (3)0.4921 (3)0.1791 (3)0.0317 (6)
H12A0.36170.49920.12140.038*
H12B0.54180.52080.15960.038*
C130.4371 (3)0.5828 (3)0.3059 (3)0.0362 (7)
H13A0.40060.66650.30600.043*
H13B0.36440.54270.33570.043*
C140.6070 (4)0.8524 (3)0.5396 (3)0.0522 (9)
H14A0.63960.91120.62430.078*
H14B0.50510.87030.50880.078*
H14C0.67690.86620.49250.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0370 (4)0.0336 (4)0.0394 (4)0.0035 (3)0.0099 (3)0.0123 (3)
S20.0336 (4)0.0329 (4)0.0374 (4)0.0030 (3)0.0037 (3)0.0122 (3)
O10.0480 (14)0.0549 (15)0.090 (2)0.0220 (12)0.0258 (13)0.0309 (14)
O20.0407 (12)0.0415 (13)0.0877 (19)0.0049 (10)0.0170 (12)0.0266 (13)
O30.0320 (10)0.0386 (11)0.0433 (12)0.0017 (8)0.0092 (9)0.0139 (9)
O40.0437 (12)0.0484 (13)0.0458 (13)0.0075 (10)0.0032 (10)0.0161 (11)
O50.0546 (14)0.0558 (15)0.0531 (14)0.0045 (11)0.0236 (11)0.0224 (12)
O60.0369 (12)0.0487 (14)0.0702 (16)0.0152 (10)0.0100 (11)0.0215 (12)
O70.0376 (12)0.0411 (13)0.0683 (16)0.0083 (9)0.0096 (10)0.0207 (11)
O80.0283 (10)0.0365 (11)0.0409 (12)0.0017 (8)0.0047 (8)0.0120 (9)
O90.0403 (12)0.0544 (14)0.0508 (14)0.0003 (10)0.0048 (10)0.0227 (11)
O100.0472 (13)0.0512 (14)0.0444 (13)0.0052 (10)0.0135 (10)0.0176 (11)
N10.0328 (13)0.0408 (15)0.0479 (16)0.0019 (11)0.0074 (11)0.0198 (12)
N20.0279 (11)0.0279 (12)0.0355 (13)0.0002 (9)0.0049 (9)0.0142 (10)
N30.0403 (14)0.0342 (14)0.0523 (16)0.0069 (11)0.0075 (12)0.0176 (12)
N40.0332 (13)0.0364 (14)0.0360 (14)0.0010 (10)0.0057 (10)0.0160 (11)
N50.0296 (12)0.0243 (11)0.0321 (12)0.0001 (9)0.0057 (9)0.0110 (10)
N70.0451 (15)0.0314 (14)0.0537 (17)0.0077 (11)0.0133 (12)0.0154 (12)
C10.0341 (16)0.056 (2)0.069 (2)0.0004 (14)0.0132 (15)0.0303 (19)
C20.0329 (15)0.0343 (16)0.0379 (17)0.0080 (12)0.0025 (12)0.0170 (13)
C30.0459 (17)0.0277 (15)0.0475 (19)0.0011 (12)0.0069 (14)0.0156 (14)
C40.0315 (14)0.0328 (15)0.0365 (16)0.0010 (11)0.0078 (12)0.0132 (13)
C50.0347 (15)0.0281 (14)0.0389 (16)0.0020 (11)0.0060 (12)0.0157 (12)
C60.0365 (15)0.0334 (16)0.0438 (18)0.0042 (12)0.0113 (13)0.0113 (13)
C70.052 (2)0.0371 (18)0.081 (3)0.0074 (15)0.0218 (18)0.0253 (18)
C80.0326 (17)0.055 (2)0.077 (3)0.0052 (15)0.0153 (16)0.0269 (19)
C90.0335 (15)0.0315 (15)0.0407 (17)0.0053 (11)0.0124 (12)0.0141 (13)
C100.0417 (17)0.0291 (15)0.0478 (18)0.0017 (12)0.0116 (13)0.0153 (14)
C110.0320 (14)0.0289 (14)0.0347 (15)0.0008 (11)0.0066 (11)0.0129 (12)
C120.0327 (14)0.0253 (13)0.0386 (16)0.0001 (11)0.0055 (12)0.0148 (12)
C130.0318 (14)0.0305 (15)0.0418 (17)0.0038 (11)0.0030 (12)0.0112 (13)
C140.0438 (18)0.0342 (17)0.076 (3)0.0022 (14)0.0064 (17)0.0221 (17)
Geometric parameters (Å, º) top
S1—O41.420 (2)C1—H1A0.9600
S1—O51.425 (2)C1—H1B0.9600
S1—O31.571 (2)C1—H1C0.9600
S1—C71.749 (3)C3—C41.367 (4)
S2—O91.423 (2)C3—H3B0.9300
S2—O101.424 (2)C5—C61.494 (4)
S2—O81.567 (2)C5—H5B0.9700
S2—C141.746 (3)C5—H5C0.9700
O1—N11.234 (3)C6—H6B0.9700
O2—N11.228 (3)C6—H6C0.9700
O3—C61.461 (3)C7—H7A0.9600
O6—N41.233 (3)C7—H7B0.9600
O7—N41.233 (3)C7—H7C0.9600
O8—C131.464 (3)C8—C91.484 (4)
N1—C41.410 (4)C8—H8A0.9600
N2—C21.363 (3)C8—H8B0.9600
N2—C41.381 (4)C8—H8C0.9600
N2—C51.473 (3)C10—C111.366 (4)
N3—C21.323 (4)C10—H10B0.9300
N3—C31.352 (4)C12—C131.490 (4)
N4—C111.406 (3)C12—H12A0.9700
N5—C91.353 (3)C12—H12B0.9700
N5—C111.383 (3)C13—H13A0.9700
N5—C121.474 (3)C13—H13B0.9700
N7—C91.328 (4)C14—H14A0.9600
N7—C101.354 (4)C14—H14B0.9600
C1—C21.467 (4)C14—H14C0.9600
O4—S1—O5118.95 (14)C6—C5—H5C109.0
O4—S1—O3109.90 (12)H5B—C5—H5C107.8
O5—S1—O3104.65 (13)O3—C6—C5107.7 (2)
O4—S1—C7109.32 (15)O3—C6—H6B110.2
O5—S1—C7109.50 (15)C5—C6—H6B110.2
O3—S1—C7103.32 (15)O3—C6—H6C110.2
O9—S2—O10118.88 (14)C5—C6—H6C110.2
O9—S2—O8104.78 (13)H6B—C6—H6C108.5
O10—S2—O8109.83 (12)S1—C7—H7A109.5
O9—S2—C14109.74 (15)S1—C7—H7B109.5
O10—S2—C14109.15 (15)H7A—C7—H7B109.5
O8—S2—C14103.28 (15)S1—C7—H7C109.5
C6—O3—S1118.58 (18)H7A—C7—H7C109.5
C13—O8—S2118.53 (17)H7B—C7—H7C109.5
O2—N1—O1123.1 (3)C9—C8—H8A109.5
O2—N1—C4119.8 (2)C9—C8—H8B109.5
O1—N1—C4117.1 (3)H8A—C8—H8B109.5
C2—N2—C4104.9 (2)C9—C8—H8C109.5
C2—N2—C5125.9 (2)H8A—C8—H8C109.5
C4—N2—C5129.1 (2)H8B—C8—H8C109.5
C2—N3—C3106.4 (2)N7—C9—N5112.3 (2)
O7—N4—O6122.9 (2)N7—C9—C8124.0 (3)
O7—N4—C11119.9 (2)N5—C9—C8123.7 (3)
O6—N4—C11117.3 (2)N7—C10—C11109.8 (3)
C9—N5—C11105.3 (2)N7—C10—H10B125.1
C9—N5—C12126.1 (2)C11—C10—H10B125.1
C11—N5—C12128.5 (2)C10—C11—N5106.9 (2)
C9—N7—C10105.7 (2)C10—C11—N4127.9 (3)
C2—C1—H1A109.5N5—C11—N4125.1 (2)
C2—C1—H1B109.5N5—C12—C13113.3 (2)
H1A—C1—H1B109.5N5—C12—H12A108.9
C2—C1—H1C109.5C13—C12—H12A108.9
H1A—C1—H1C109.5N5—C12—H12B108.9
H1B—C1—H1C109.5C13—C12—H12B108.9
N3—C2—N2112.0 (3)H12A—C12—H12B107.7
N3—C2—C1124.5 (3)O8—C13—C12108.1 (2)
N2—C2—C1123.6 (3)O8—C13—H13A110.1
N3—C3—C4109.2 (3)C12—C13—H13A110.1
N3—C3—H3B125.4O8—C13—H13B110.1
C4—C3—H3B125.4C12—C13—H13B110.1
C3—C4—N2107.5 (2)H13A—C13—H13B108.4
C3—C4—N1127.4 (3)S2—C14—H14A109.5
N2—C4—N1125.1 (2)S2—C14—H14B109.5
N2—C5—C6113.0 (2)H14A—C14—H14B109.5
N2—C5—H5B109.0S2—C14—H14C109.5
C6—C5—H5B109.0H14A—C14—H14C109.5
N2—C5—H5C109.0H14B—C14—H14C109.5
O4—S1—O3—C636.6 (2)C4—N2—C5—C680.8 (3)
O5—S1—O3—C6165.4 (2)S1—O3—C6—C5174.80 (18)
C7—S1—O3—C679.9 (2)N2—C5—C6—O377.7 (3)
O9—S2—O8—C13165.3 (2)C10—N7—C9—N50.1 (3)
O10—S2—O8—C1336.5 (2)C10—N7—C9—C8179.2 (3)
C14—S2—O8—C1379.8 (2)C11—N5—C9—N70.4 (3)
C3—N3—C2—N20.8 (3)C12—N5—C9—N7176.3 (3)
C3—N3—C2—C1179.1 (3)C11—N5—C9—C8179.0 (3)
C4—N2—C2—N31.0 (3)C12—N5—C9—C84.4 (5)
C5—N2—C2—N3176.3 (3)C9—N7—C10—C110.2 (3)
C4—N2—C2—C1178.8 (3)N7—C10—C11—N50.4 (3)
C5—N2—C2—C13.9 (4)N7—C10—C11—N4177.2 (3)
C2—N3—C3—C40.2 (3)C9—N5—C11—C100.5 (3)
N3—C3—C4—N20.4 (3)C12—N5—C11—C10176.1 (3)
N3—C3—C4—N1179.7 (3)C9—N5—C11—N4177.3 (3)
C2—N2—C4—C30.9 (3)C12—N5—C11—N46.1 (4)
C5—N2—C4—C3176.3 (3)O7—N4—C11—C10172.6 (3)
C2—N2—C4—N1179.3 (3)O6—N4—C11—C107.8 (4)
C5—N2—C4—N13.5 (5)O7—N4—C11—N54.7 (4)
O2—N1—C4—C3175.3 (3)O6—N4—C11—N5174.9 (3)
O1—N1—C4—C34.2 (5)C9—N5—C12—C13102.3 (3)
O2—N1—C4—N24.9 (4)C11—N5—C12—C1381.8 (3)
O1—N1—C4—N2175.7 (3)S2—O8—C13—C12174.36 (17)
C2—N2—C5—C6102.5 (3)N5—C12—C13—O877.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O6i0.972.503.235 (4)133
C5—H5C···N7ii0.972.543.484 (4)165
C7—H7B···O9iii0.962.593.498 (4)157
C7—H7C···O10iv0.962.523.423 (4)157
C12—H12A···O1v0.972.503.250 (5)134
C12—H12B···N3vi0.972.533.472 (4)164
C14—H14B···O5vii0.962.593.507 (4)160
C14—H14C···O4viii0.962.553.414 (4)150
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) x1, y1, z; (iv) x, y1, 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 formulaC7H11N3O5S
Mr249.26
Crystal system, space groupTriclinic, 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)
V3)1052.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.40 × 0.21 × 0.08
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.883, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
11649, 3918, 3078
Rint0.033
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.152, 1.07
No. of reflections3918
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O6i0.97002.50003.235 (4)133.00
C5—H5C···N7ii0.97002.54003.484 (4)165.00
C7—H7B···O9iii0.96002.59003.498 (4)157.00
C7—H7C···O10iv0.96002.52003.423 (4)157.00
C12—H12A···O1v0.97002.50003.250 (5)134.00
C12—H12B···N3vi0.97002.53003.472 (4)164.00
C14—H14B···O5vii0.96002.59003.507 (4)160.00
C14—H14C···O4viii0.96002.55003.414 (4)150.00
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) x1, y1, z; (iv) x, y1, 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

First citationBruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationNardelli, M. (1995). J. Appl. Cryst. 28, 659.  CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationYousuf, S., Zeb, A. & Basha, F. Z. (2012). Acta Cryst. E68, o952.  CSD CrossRef IUCr Journals
First citationZeb, A., Malik, I., Rasheed, S., Choudhary, M. I. & Basha, F. Z. (2012). Med. Chem. 8, 846–852.  CrossRef CAS PubMed
First citationZeb, A., Yousuf, S. & Basha, F. Z. (2012). Acta Cryst. E68, o1218.  CSD CrossRef IUCr Journals

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