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

Khan, S.B.; Anis, I.; Singh, K.; Shah, M.R.

doi:10.1107/S1600536810004186

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o548

doi:10.1107/S1600536810004186

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

Sher Bahadar Khan,^a Itrat Anis,^b Kuldip Singh ^c and Muhammad Raza Shah ^d ^*

^aDepartment of Chemical Engineering, Yonsei University, 134, Shincheon-dong, Seodaemun-gu, Seoul 120-749, Republic of Korea, ^bDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, ^cDepartment of Chemistry, University of Leicester, George Porter Building, University Road, Leicester LE1 7RH, England, and ^dH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: raza_shahm@yahoo.com

(Received 20 January 2010; accepted 2 February 2010; online 6 February 2010)

In the title compound, C₁₃H₁₂N₄O₆, the mean plane through the nitrobenzene forms a dihedral angle of 37.38 (15)° with the plane through the imidazole ring. The crystal packing is stabilized by weak intermolecular C—H⋯O and C—H⋯N interactions together with π–π stacking interactions between nitrobenzene rings [centroid–centroid distance = 3.788 (3) Å] and between imidazole rings [centroid–centroid distance = 3.590 (2) Å].

Related literature

For the pharmacological uses of metronidazole, see: Mao et al. (2009 ); Cosar et al. (1966 ); Bowden & Izadi (1997 ). For a related structure, see: Bahadur et al. (2009 ). For additional structural analysis, see: Spek (2009 ).

Experimental

Crystal data

C₁₃H₁₂N₄O₆
M_r = 320.27
Monoclinic, P 2₁ /c
a = 15.392 (8) Å
b = 8.605 (4) Å
c = 10.968 (5) Å
β = 106.576 (9)°
V = 1392.3 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 150 K
0.27 × 0.24 × 0.08 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.573, T_max = 0.969
9743 measured reflections
2444 independent reflections
1700 reflections with I > \2s(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.129
S = 1.00
2444 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O5ⁱ	0.95	2.58	3.474 (4)	157
C9—H9B⋯O6ⁱⁱ	0.99	2.45	3.166 (3)	129
C9—H9B⋯O5	0.99	2.39	2.838 (3)	107
C9—H9A⋯N2ⁱⁱⁱ	0.99	2.57	3.513 (4)	159
C7—H7⋯O3^iv	0.95	2.43	3.190 (4)	137
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004186/tk2618sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004186/tk2618Isup2.hkl

checkCIF report

Comment top

Metronidazole,1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole, is an antibiotic which is effective against anaerobic bacteria and certain parasites (Mao et al., 2009). However, there are problems related to its low aqueous solubility, toxicity and poor absorption characteristics (Bowden & Izadi 1997). In order to improve the water-solubility of metronidazole, certain esters and hemi-esters of metronidazole have been prepared (Cosar et al., 1966) which have shown better solubility in aqueous medium compared to the parent metronidazole. Here, we are reporting the synthesis and crystal structure of an ester derivative of metronidazole, (I).

The molecule of (I), Fig. 1, is non-planar with a dihedral angle of 37.38 (15) ° formed between the mean planes through the nitrobenzene and imidazole rings (Spek, 2009). The nitro group is co-planar with the imidazole ring to which it is connected [dihedral angle 0.90 (3) °] , while the phenyl-nitro group is slightly twisted out of the plane of the benzene ring, forming a dihedral angle of 8.13 (3) °. The key C═O and C—N bond distances are in agreement with those observed in the related structure of 2-(2-methyl-5-nitro-1 H-imidazol-1-yl) ethyl 3-bromobenzoate (Bahadur et al., 2009). The crystal packing is stabilized by weak intermolecular C—H···O and C—H···N interactions, Table 1 , together with π-π stacking interactions with the shortest of these occuring between symmetry related imidazole rings [ring centroid (N1–C12)··· ring centroid (N1–C12)ⁱ =3.590 (2) Å for ii: 1-x, -y, 1-z]. In addition, π···π contacts are noted between symmetry related nitrobenzene rings [ring centroid (C2–C7)···ring centroid (C2–C7)ⁱⁱ = 3.788 (3) Å for ii : 1-x, 2-y, 1-z].

Related literature top

For the pharmacological uses of metronidazole, see: Mao et al. (2009); Cosar et al. (1966); Bowden & Izadi (1997). For a related structure, see: Bahadur et al. (2009). For additional structural analysis, see: Spek (2009).

Experimental top

Metronidazole (5 g, 29.23 mmol) was added to 4-nitrobenzoic acid (9.38 g, 56.11 mmol) dissolved in anhydrous CH₂Cl₂ (10 ml). Then, 4-dimethylaminopyridine (0.15 equiv.) and dicyclohexylcarbodiimide (1.25 equiv) were added, and the resulting solution stirred. After 12 h, the solvent was evaporated under reduced pressure. The crude reaction mixture was subjected to flash column chromatography over silica gel, successively eluting with n-hexane–ethyl acetate (2.8: 7.2) which afforded (I) in 73 % yield. Colorless crystals were obtained from the slow evaporation of a CH₂Cl₂ solution of (I).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SHELXTL (Sheldrick, 2008); 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).

Figures top

Fig. 1. Molecular Structure of (I) with atom labelling scheme and 30% probability displacement ellipsoids.

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

Crystal data top

C₁₃H₁₂N₄O₆	F(000) = 664
M_r = 320.27	D_x = 1.528 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 721 reflections
a = 15.392 (8) Å	θ = 2.8–23.3°
b = 8.605 (4) Å	µ = 0.12 mm⁻¹
c = 10.968 (5) Å	T = 150 K
β = 106.576 (9)°	Plate, yellow
V = 1392.3 (12) Å³	0.27 × 0.24 × 0.08 mm
Z = 4

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	2444 independent reflections
Radiation source: fine-focus sealed tube	1700 reflections with I > \2s(I)
Graphite monochromator	R_int = 0.099
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −18→18
T_min = 0.573, T_max = 0.969	k = −10→10
9743 measured reflections	l = −13→12

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) = 0.129	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0572P)²] where P = (F_o² + 2F_c²)/3
2444 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₃H₁₂N₄O₆	V = 1392.3 (12) Å³
M_r = 320.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.392 (8) Å	µ = 0.12 mm⁻¹
b = 8.605 (4) Å	T = 150 K
c = 10.968 (5) Å	0.27 × 0.24 × 0.08 mm
β = 106.576 (9)°

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	2444 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	1700 reflections with I > \2s(I)
T_min = 0.573, T_max = 0.969	R_int = 0.099
9743 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
2444 reflections	Δρ_min = −0.23 e Å⁻³
209 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.23596 (12)	0.70542 (19)	0.54231 (16)	0.0328 (5)
O2	0.09150 (14)	0.6281 (2)	0.5020 (2)	0.0531 (6)
O3	0.17653 (15)	0.8476 (3)	0.73301 (19)	0.0554 (6)
O4	0.17995 (15)	1.0918 (3)	0.7714 (2)	0.0678 (7)
O5	0.33567 (14)	0.2348 (2)	0.51061 (18)	0.0456 (6)
O6	0.35085 (16)	0.1756 (2)	0.3260 (2)	0.0535 (6)
N1	0.38462 (14)	0.5437 (2)	0.47700 (18)	0.0274 (5)
N2	0.42041 (15)	0.6345 (3)	0.3073 (2)	0.0349 (6)
N3	0.16552 (16)	0.9819 (3)	0.6976 (2)	0.0429 (6)
N4	0.35352 (16)	0.2691 (3)	0.4118 (2)	0.0359 (6)
C1	0.14715 (19)	0.7286 (3)	0.5095 (2)	0.0335 (6)
C2	0.12371 (17)	0.8940 (3)	0.4747 (3)	0.0336 (7)
C3	0.13293 (17)	1.0152 (3)	0.5613 (3)	0.0342 (7)
C4	0.10931 (18)	1.1655 (3)	0.5259 (3)	0.0419 (8)
H4	0.1170	1.2449	0.5882	0.050*
C5	0.0745 (2)	1.1999 (4)	0.3993 (3)	0.0490 (8)
H5	0.0576	1.3035	0.3732	0.059*
C6	0.0642 (2)	1.0840 (4)	0.3104 (3)	0.0500 (8)
H6	0.0395	1.1076	0.2227	0.060*
C7	0.08938 (19)	0.9331 (4)	0.3477 (3)	0.0434 (7)
H7	0.0830	0.8546	0.2848	0.052*
C8	0.26654 (18)	0.5514 (3)	0.5882 (2)	0.0327 (6)
H8A	0.2339	0.4717	0.5272	0.039*
H8B	0.2552	0.5323	0.6713	0.039*
C9	0.36572 (17)	0.5446 (3)	0.6016 (2)	0.0287 (6)
H9A	0.3959	0.6354	0.6514	0.034*
H9B	0.3915	0.4495	0.6492	0.034*
C10	0.40945 (17)	0.6699 (3)	0.4201 (2)	0.0306 (6)
C11	0.40087 (18)	0.4813 (3)	0.2895 (2)	0.0351 (7)
H11	0.4019	0.4231	0.2163	0.042*
C12	0.37939 (18)	0.4234 (3)	0.3933 (2)	0.0299 (6)
C13	0.4210 (2)	0.8282 (3)	0.4750 (3)	0.0405 (7)
H13A	0.4510	0.8942	0.4264	0.061*
H13B	0.4582	0.8232	0.5638	0.061*
H13C	0.3615	0.8718	0.4712	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0350 (11)	0.0268 (10)	0.0376 (11)	0.0009 (8)	0.0123 (9)	0.0037 (8)
O2	0.0401 (12)	0.0407 (13)	0.0799 (16)	−0.0053 (10)	0.0196 (11)	0.0035 (11)
O3	0.0745 (16)	0.0549 (16)	0.0435 (14)	0.0126 (12)	0.0276 (12)	0.0088 (11)
O4	0.0684 (17)	0.0673 (17)	0.0586 (15)	0.0159 (13)	0.0036 (13)	−0.0246 (13)
O5	0.0764 (16)	0.0276 (11)	0.0378 (12)	−0.0041 (10)	0.0242 (11)	0.0047 (9)
O6	0.0910 (18)	0.0274 (11)	0.0468 (13)	−0.0035 (11)	0.0272 (12)	−0.0119 (10)
N1	0.0364 (13)	0.0205 (12)	0.0267 (12)	0.0006 (9)	0.0109 (10)	0.0008 (9)
N2	0.0456 (14)	0.0312 (14)	0.0310 (13)	0.0002 (11)	0.0159 (11)	0.0028 (10)
N3	0.0360 (14)	0.0465 (17)	0.0478 (17)	0.0069 (12)	0.0143 (12)	−0.0085 (14)
N4	0.0512 (15)	0.0251 (13)	0.0329 (14)	0.0018 (11)	0.0144 (12)	−0.0017 (11)
C1	0.0320 (16)	0.0359 (17)	0.0340 (16)	−0.0031 (13)	0.0115 (13)	−0.0009 (13)
C2	0.0281 (15)	0.0340 (16)	0.0417 (17)	−0.0003 (12)	0.0147 (13)	0.0030 (13)
C3	0.0250 (14)	0.0397 (18)	0.0394 (17)	0.0017 (12)	0.0115 (12)	−0.0014 (13)
C4	0.0341 (17)	0.0337 (17)	0.061 (2)	0.0015 (13)	0.0191 (15)	−0.0012 (15)
C5	0.0392 (18)	0.0387 (19)	0.072 (2)	0.0058 (14)	0.0208 (17)	0.0174 (18)
C6	0.0432 (19)	0.059 (2)	0.0473 (19)	0.0058 (16)	0.0127 (15)	0.0210 (18)
C7	0.0394 (18)	0.0483 (19)	0.0446 (19)	0.0006 (15)	0.0155 (15)	0.0031 (15)
C8	0.0459 (17)	0.0227 (14)	0.0334 (15)	0.0011 (12)	0.0177 (13)	0.0017 (11)
C9	0.0422 (16)	0.0215 (14)	0.0247 (14)	0.0032 (12)	0.0134 (12)	0.0015 (11)
C10	0.0365 (16)	0.0220 (15)	0.0345 (16)	0.0023 (12)	0.0122 (12)	0.0060 (12)
C11	0.0459 (18)	0.0310 (17)	0.0311 (16)	0.0018 (13)	0.0151 (13)	−0.0024 (12)
C12	0.0425 (17)	0.0200 (14)	0.0285 (14)	0.0023 (12)	0.0120 (12)	−0.0020 (11)
C13	0.0504 (19)	0.0251 (16)	0.0480 (18)	−0.0049 (13)	0.0172 (15)	0.0009 (13)

Geometric parameters (Å, º) top

O1—C1	1.326 (3)	C4—C5	1.370 (4)
O1—C8	1.448 (3)	C4—H4	0.9500
O2—C1	1.204 (3)	C5—C6	1.371 (4)
O3—N3	1.216 (3)	C5—H5	0.9500
O4—N3	1.223 (3)	C6—C7	1.384 (4)
O5—N4	1.227 (3)	C6—H6	0.9500
O6—N4	1.230 (3)	C7—H7	0.9500
N1—C10	1.360 (3)	C8—C9	1.492 (4)
N1—C12	1.371 (3)	C8—H8A	0.9900
N1—C9	1.476 (3)	C8—H8B	0.9900
N2—C10	1.331 (3)	C9—H9A	0.9900
N2—C11	1.354 (3)	C9—H9B	0.9900
N3—C3	1.462 (4)	C10—C13	1.479 (4)
N4—C12	1.417 (3)	C11—C12	1.367 (3)
C1—C2	1.491 (4)	C11—H11	0.9500
C2—C7	1.383 (4)	C13—H13A	0.9800
C2—C3	1.390 (4)	C13—H13B	0.9800
C3—C4	1.369 (4)	C13—H13C	0.9800

C1—O1—C8	116.1 (2)	C2—C7—H7	119.3
C10—N1—C12	105.4 (2)	C6—C7—H7	119.3
C10—N1—C9	125.2 (2)	O1—C8—C9	107.0 (2)
C12—N1—C9	129.4 (2)	O1—C8—H8A	110.3
C10—N2—C11	106.0 (2)	C9—C8—H8A	110.3
O3—N3—O4	122.8 (3)	O1—C8—H8B	110.3
O3—N3—C3	119.2 (2)	C9—C8—H8B	110.3
O4—N3—C3	118.0 (3)	H8A—C8—H8B	108.6
O5—N4—O6	123.5 (2)	N1—C9—C8	112.0 (2)
O5—N4—C12	119.6 (2)	N1—C9—H9A	109.2
O6—N4—C12	116.9 (2)	C8—C9—H9A	109.2
O2—C1—O1	124.7 (3)	N1—C9—H9B	109.2
O2—C1—C2	123.6 (3)	C8—C9—H9B	109.2
O1—C1—C2	111.6 (2)	H9A—C9—H9B	107.9
C7—C2—C3	116.2 (3)	N2—C10—N1	111.7 (2)
C7—C2—C1	119.0 (3)	N2—C10—C13	123.8 (2)
C3—C2—C1	124.8 (3)	N1—C10—C13	124.4 (2)
C4—C3—C2	123.2 (3)	N2—C11—C12	109.3 (2)
C4—C3—N3	117.5 (3)	N2—C11—H11	125.3
C2—C3—N3	119.3 (2)	C12—C11—H11	125.3
C3—C4—C5	119.2 (3)	C11—C12—N1	107.5 (2)
C3—C4—H4	120.4	C11—C12—N4	127.2 (2)
C5—C4—H4	120.4	N1—C12—N4	125.2 (2)
C4—C5—C6	119.7 (3)	C10—C13—H13A	109.5
C4—C5—H5	120.1	C10—C13—H13B	109.5
C6—C5—H5	120.1	H13A—C13—H13B	109.5
C5—C6—C7	120.4 (3)	C10—C13—H13C	109.5
C5—C6—H6	119.8	H13A—C13—H13C	109.5
C7—C6—H6	119.8	H13B—C13—H13C	109.5
C2—C7—C6	121.3 (3)

C8—O1—C1—O2	−8.7 (4)	C1—O1—C8—C9	172.1 (2)
C8—O1—C1—C2	175.0 (2)	C10—N1—C9—C8	99.1 (3)
O2—C1—C2—C7	−72.3 (4)	C12—N1—C9—C8	−79.0 (3)
O1—C1—C2—C7	104.2 (3)	O1—C8—C9—N1	−70.4 (3)
O2—C1—C2—C3	107.2 (3)	C11—N2—C10—N1	0.9 (3)
O1—C1—C2—C3	−76.4 (3)	C11—N2—C10—C13	−177.9 (3)
C7—C2—C3—C4	0.5 (4)	C12—N1—C10—N2	−0.4 (3)
C1—C2—C3—C4	−178.9 (3)	C9—N1—C10—N2	−178.9 (2)
C7—C2—C3—N3	177.7 (2)	C12—N1—C10—C13	178.3 (3)
C1—C2—C3—N3	−1.7 (4)	C9—N1—C10—C13	−0.2 (4)
O3—N3—C3—C4	171.1 (3)	C10—N2—C11—C12	−1.0 (3)
O4—N3—C3—C4	−8.4 (4)	N2—C11—C12—N1	0.7 (3)
O3—N3—C3—C2	−6.3 (4)	N2—C11—C12—N4	178.9 (3)
O4—N3—C3—C2	174.2 (3)	C10—N1—C12—C11	−0.2 (3)
C2—C3—C4—C5	0.3 (4)	C9—N1—C12—C11	178.2 (2)
N3—C3—C4—C5	−177.0 (2)	C10—N1—C12—N4	−178.4 (2)
C3—C4—C5—C6	−0.2 (4)	C9—N1—C12—N4	0.0 (4)
C4—C5—C6—C7	−0.5 (4)	O5—N4—C12—C11	−179.6 (3)
C3—C2—C7—C6	−1.3 (4)	O6—N4—C12—C11	0.8 (4)
C1—C2—C7—C6	178.2 (3)	O5—N4—C12—N1	−1.7 (4)
C5—C6—C7—C2	1.4 (4)	O6—N4—C12—N1	178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O5ⁱ	0.95	2.58	3.474 (4)	157
C9—H9B···O6ⁱⁱ	0.99	2.45	3.166 (3)	129
C9—H9B···O5	0.99	2.39	2.838 (3)	107
C9—H9A···N2ⁱⁱⁱ	0.99	2.57	3.513 (4)	159
C7—H7···O3^iv	0.95	2.43	3.190 (4)	137

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₄O₆
M_r	320.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	15.392 (8), 8.605 (4), 10.968 (5)
β (°)	106.576 (9)
V (Å³)	1392.3 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.27 × 0.24 × 0.08

Data collection
Diffractometer	Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.573, 0.969
No. of measured, independent and observed [I > \2s(I)] reflections	9743, 2444, 1700
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.129, 1.00
No. of reflections	2444
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O5ⁱ	0.95	2.58	3.474 (4)	156.6
C9—H9B···O6ⁱⁱ	0.99	2.45	3.166 (3)	128.8
C9—H9B···O5	0.99	2.39	2.838 (3)	106.6
C9—H9A···N2ⁱⁱⁱ	0.99	2.57	3.513 (4)	158.6
C7—H7···O3^iv	0.95	2.43	3.190 (4)	137.2

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2.

Acknowledgements

The authors thank the Pakistan Science Foundation for financial support.

References

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