2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl methane­sulfonate

Yousuf, S.; Zeb, A.; Batool, F.; Basha, F.Z.

doi:10.1107/S1600536812034964

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2781

doi:10.1107/S1600536812034964

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2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl methanesulfonate

Sammer Yousuf,^a ^* Aurang Zeb,^a Farhana Batool ^a and Fatima Z. Basha ^a ‡

^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 ). For related structures, see: Yousuf et al. (2012 ); Zeb, Yousuf et al. (2012 ).

Experimental

Crystal data

C₇H₁₁N₃O₅S
M_r = 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 ) T_min = 0.883, T_max = 0.975
11649 measured reflections
3918 independent reflections
3078 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.152
S = 1.07
3918 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O10^iv	0.96	2.52	3.423 (4)	157
C12—H12A⋯O1^v	0.97	2.50	3.250 (5)	134
C12—H12B⋯N3^vi	0.97	2.53	3.472 (4)	164
C14—H14B⋯O5^vii	0.96	2.59	3.507 (4)	160
C14—H14C⋯O4^viii	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); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034964/pv2579sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034964/pv2579Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034964/pv2579Isup3.cml

checkCIF report

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.

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

C₇H₁₁N₃O₅S	Z = 4
M_r = 249.26	F(000) = 520
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3918 independent reflections
Radiation source: fine-focus sealed tube	3078 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scan	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.883, T_max = 0.975	k = −13→13
11649 measured reflections	l = −14→14

Refinement top

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(F_o²) + (0.0914P)² + 0.2849P] where P = (F_o² + 2F_c²)/3
3918 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₇H₁₁N₃O₅S	γ = 90.052 (4)°
M_r = 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)°

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)
T_min = 0.883, T_max = 0.975	R_int = 0.033
11649 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.07	Δρ_max = 0.79 e Å⁻³
3918 reflections	Δρ_min = −0.32 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O10^iv	0.96	2.52	3.423 (4)	157
C12—H12A···O1^v	0.97	2.50	3.250 (5)	134
C12—H12B···N3^vi	0.97	2.53	3.472 (4)	164
C14—H14B···O5^vii	0.96	2.59	3.507 (4)	160
C14—H14C···O4^viii	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
M_r	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)
T_min, T_max	0.883, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	11649, 3918, 3078
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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···O10^iv	0.9600	2.5200	3.423 (4)	157.00
C12—H12A···O1^v	0.9700	2.5000	3.250 (5)	134.00
C12—H12B···N3^vi	0.9700	2.5300	3.472 (4)	164.00
C14—H14B···O5^vii	0.9600	2.5900	3.507 (4)	160.00
C14—H14C···O4^viii	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