N-{4-[(5-Methyl­isoxazol-3-yl)sulfamo­yl]phen­yl}benzamide

Yasmeen, S.; Murtaza, S.; Akkurt, M.; Khan, I.U.; Sharif, S.

doi:10.1107/S1600536810031132

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2264

https://doi.org/10.1107/S1600536810031132

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N-{4-[(5-Methylisoxazol-3-yl)sulfamoyl]phenyl}benzamide

Sumera Yasmeen,^a Shahzad Murtaza,^a Mehmet Akkurt,^b ^* Islam Ullah Khan ^c ‡ and Shahzad Sharif ^c

^aDepartment of Chemistry, University of Gujrat, Gujrat 50700, Pakistan, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 27 July 2010; accepted 3 August 2010; online 11 August 2010)

In the title compound, C₁₇H₁₅N₃O₄S, the five-membered isoxazole ring makes dihedral angles of 80.5 (2) and 81.3 (2)° with the two benzene rings, which form a dihedral angle of 39.81 (18)° with each other. A short intramolecular C—H⋯O contact occurs. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which generate [001] chains, and further consolidated by weak C—H⋯O interactions.

Related literature

The N-alkylated moiety is present in many natural products as well as in drugs, see: Wijayanti et al. (2010 ). For the synthesis and the biological properties of amide derivatives of sulfonamide-type drugs, see: Hussain (2009 ). For the crystal structures of similar sulfonamides, see: Shad et al. (2008 , 2009 ); Chohan et al. (2008a ,b ); Tahir et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₅N₃O₄S
M_r = 357.39
Monoclinic, P 2₁ /c
a = 8.2407 (6) Å
b = 23.5069 (16) Å
c = 8.5199 (6) Å
β = 92.155 (3)°
V = 1649.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.34 × 0.17 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
12756 measured reflections
2865 independent reflections
1544 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.135
S = 0.99
2865 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O4ⁱ	0.86	2.21	2.788 (4)	124
N3—H3N⋯O3ⁱⁱ	0.86	2.27	3.075 (4)	156
C7—H7⋯O4	0.93	2.26	2.832 (4)	119
C10—H10⋯O2ⁱⁱⁱ	0.93	2.44	3.130 (4)	131
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x, y, z+1; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810031132/hb5581sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031132/hb5581Isup2.hkl

checkCIF report

Comment top

N-alkylated moiety is present in many natural products as well as in drugs (Wijayanti et al., 2010). Amide derivative of sulfonamide type drugs has been synthesized and biologicaly evaluated (Hussain, 2009). The title compound (I), a new benzamide derivative of sulfamethaxazole, was synthesized by the condensation reaction of sulfamethaxazole with benzoyl chloride.

In (I), (Fig. 1), the bond lengths and bond angles of the molecule are in good agreement with those determined in the similar compounds (Shad et al., 2009; Chohan et al., 2008a,b; Shad et al., 2008; Tahir et al., 2008). The five-membered isoxazole ring (O1/N1/C2–C4) make dihedral angles of 80.5 (2) and 81.3 (2)° with the two benzene rings (C5–C10) and (C12–C17) which form a dihedral angle of 39.81 (18)° with each other. In (I), The torsion angles C1—C2–C3–C4, O4—C11—C12—C13, C1—N2—S1—C5 and C8—N3—C11—C12 are -177.5 (5), -16.4 (5), -69.4 (3) and 167.0 (3)°, respectively.

The crystal packing of (I) is stabilized by intermolecular N—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 2), forming an extended supramolecular network.

Related literature top

The N-alkylated moiety is present in many natural products as well as in drugs, see: Wijayanti et al. (2010). For the synthesis and the biological properties of amide derivatives of sulfonamide-type drugs, see: Hussain (2009). For the crystal structures of similar sulfonamides, see: Shad et al. (2009); Chohan et al. (2008a,b); Shad et al. (2008); Tahir et al. (2008).

Experimental top

Sulfamethaxazole (100 mg, 0.39 mmol) was dissolved in methanol (10 ml) and then benzoyl chloride (45 ml, 0.39 mmol) was added dropwise. The mixture was refluxed for 2 h at temperature ~353 K. The pH of the reaction was maintained at 7–8 by adding pyridine to neuterlize the produced HCl. White precipitates were formed. The precipitates were filtered, washed with plenty of distilled water and crystallized with acetone to yield off-white blocks of (I).

Structure description top

The crystal packing of (I) is stabilized by intermolecular N—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 2), forming an extended supramolecular network.

The N-alkylated moiety is present in many natural products as well as in drugs, see: Wijayanti et al. (2010). For the synthesis and the biological properties of amide derivatives of sulfonamide-type drugs, see: Hussain (2009). For the crystal structures of similar sulfonamides, see: Shad et al. (2009); Chohan et al. (2008a,b); Shad et al. (2008); Tahir et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. A partial view of the packing of (I), showing the N—H ··· O and C—H ··· O hydrogen-bonding interactions (dashed lines) between the molecules. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

N-{4-[(5-Methylisoxazol-3-yl)sulfamoyl]phenyl}benzamide top

Crystal data top

C₁₇H₁₅N₃O₄S	F(000) = 744
M_r = 357.39	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 886 reflections
a = 8.2407 (6) Å	θ = 2.5–19.0°
b = 23.5069 (16) Å	µ = 0.22 mm⁻¹
c = 8.5199 (6) Å	T = 296 K
β = 92.155 (3)°	Block, off-white
V = 1649.3 (2) Å³	0.34 × 0.17 × 0.07 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	1544 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.099
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
phi and ω scans	h = −9→9
12756 measured reflections	k = −27→27
2865 independent reflections	l = −9→10

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0555P)²] where P = (F_o² + 2F_c²)/3
2865 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₇H₁₅N₃O₄S	V = 1649.3 (2) Å³
M_r = 357.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2407 (6) Å	µ = 0.22 mm⁻¹
b = 23.5069 (16) Å	T = 296 K
c = 8.5199 (6) Å	0.34 × 0.17 × 0.07 mm
β = 92.155 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1544 reflections with I > 2σ(I)
12756 measured reflections	R_int = 0.099
2865 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 0.99	Δρ_max = 0.26 e Å⁻³
2865 reflections	Δρ_min = −0.33 e Å⁻³
227 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.43740 (12)	0.83329 (4)	−0.22084 (11)	0.0386 (4)
O1	1.0003 (4)	0.81880 (17)	−0.0861 (4)	0.0844 (17)
O2	0.4214 (3)	0.77361 (9)	−0.1980 (3)	0.0496 (10)
O3	0.3429 (3)	0.86108 (10)	−0.3422 (3)	0.0496 (10)
O4	0.3631 (3)	1.03832 (10)	0.3334 (3)	0.0510 (10)
N1	0.8855 (5)	0.85441 (16)	−0.1611 (5)	0.0704 (17)
N2	0.6255 (4)	0.84586 (12)	−0.2644 (3)	0.0437 (11)
N3	0.3130 (4)	0.94599 (12)	0.3837 (3)	0.0404 (11)
C1	1.0426 (6)	0.7243 (2)	0.0112 (7)	0.108 (3)
C2	0.9324 (7)	0.7675 (2)	−0.0637 (5)	0.070 (2)
C3	0.7813 (6)	0.76770 (19)	−0.1215 (5)	0.0652 (19)
C4	0.7578 (5)	0.82254 (18)	−0.1798 (4)	0.0452 (16)
C5	0.4049 (4)	0.86758 (14)	−0.0421 (4)	0.0323 (12)
C6	0.3831 (4)	0.92538 (14)	−0.0387 (4)	0.0363 (12)
C7	0.3562 (4)	0.95266 (15)	0.0996 (4)	0.0372 (14)
C8	0.3494 (4)	0.92116 (15)	0.2385 (4)	0.0344 (12)
C9	0.3738 (5)	0.86339 (15)	0.2337 (4)	0.0414 (14)
C10	0.4019 (4)	0.83617 (15)	0.0942 (4)	0.0417 (14)
C11	0.3098 (4)	1.00198 (16)	0.4204 (4)	0.0364 (12)
C12	0.2330 (4)	1.01807 (15)	0.5708 (4)	0.0367 (12)
C13	0.2608 (5)	1.07230 (17)	0.6286 (4)	0.0495 (17)
C14	0.1852 (6)	1.09083 (19)	0.7601 (5)	0.0651 (19)
C15	0.0811 (5)	1.0556 (2)	0.8348 (5)	0.0610 (19)
C16	0.0515 (5)	1.00162 (19)	0.7787 (4)	0.0528 (17)
C17	0.1291 (4)	0.98271 (16)	0.6476 (4)	0.0430 (14)
H1A	1.09040	0.73950	0.10680	0.1620*
H1B	1.12680	0.71480	−0.05920	0.1620*
H1C	0.98170	0.69070	0.03430	0.1620*
H2N	0.64370	0.86780	−0.34260	0.0530*
H3	0.70730	0.73780	−0.12300	0.0780*
H3N	0.29020	0.92280	0.45780	0.0480*
H6	0.38660	0.94620	−0.13130	0.0430*
H7	0.34250	0.99190	0.10140	0.0450*
H9	0.37120	0.84230	0.32600	0.0500*
H10	0.41880	0.79710	0.09210	0.0500*
H13	0.33130	1.09640	0.57800	0.0600*
H14	0.20470	1.12730	0.79820	0.0780*
H15	0.03020	1.06810	0.92400	0.0730*
H16	−0.02050	0.97790	0.82880	0.0630*
H17	0.11110	0.94590	0.61100	0.0510*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0542 (7)	0.0308 (6)	0.0309 (6)	−0.0024 (5)	0.0013 (4)	−0.0030 (5)
O1	0.066 (3)	0.095 (3)	0.091 (3)	0.007 (2)	−0.0124 (19)	−0.007 (2)
O2	0.075 (2)	0.0238 (14)	0.0500 (18)	−0.0059 (13)	0.0019 (14)	−0.0043 (12)
O3	0.068 (2)	0.0470 (17)	0.0330 (16)	0.0020 (13)	−0.0096 (13)	0.0012 (13)
O4	0.078 (2)	0.0357 (16)	0.0409 (17)	−0.0104 (14)	0.0217 (14)	−0.0015 (13)
N1	0.057 (3)	0.063 (3)	0.090 (3)	0.003 (2)	−0.013 (2)	−0.007 (2)
N2	0.051 (2)	0.045 (2)	0.0359 (19)	0.0010 (16)	0.0138 (16)	0.0054 (15)
N3	0.059 (2)	0.0325 (19)	0.0302 (18)	0.0013 (15)	0.0085 (15)	0.0036 (14)
C1	0.067 (4)	0.142 (5)	0.116 (5)	0.039 (4)	0.008 (3)	0.046 (4)
C2	0.066 (4)	0.090 (4)	0.055 (3)	0.021 (3)	0.015 (3)	0.016 (3)
C3	0.049 (3)	0.068 (3)	0.079 (4)	0.009 (2)	0.006 (3)	0.023 (3)
C4	0.045 (3)	0.050 (3)	0.041 (2)	0.003 (2)	0.009 (2)	−0.010 (2)
C5	0.040 (2)	0.029 (2)	0.028 (2)	−0.0013 (17)	0.0020 (17)	0.0018 (17)
C6	0.041 (2)	0.039 (2)	0.029 (2)	−0.0008 (18)	0.0010 (17)	0.0069 (18)
C7	0.051 (3)	0.026 (2)	0.035 (2)	0.0019 (17)	0.0062 (18)	0.0030 (17)
C8	0.041 (2)	0.036 (2)	0.026 (2)	−0.0044 (17)	0.0004 (16)	0.0011 (17)
C9	0.061 (3)	0.029 (2)	0.034 (2)	−0.0002 (18)	0.0012 (19)	0.0085 (18)
C10	0.063 (3)	0.024 (2)	0.038 (2)	0.0000 (19)	0.0026 (19)	−0.0013 (18)
C11	0.037 (2)	0.040 (2)	0.032 (2)	0.0011 (18)	−0.0022 (17)	−0.0021 (19)
C12	0.035 (2)	0.046 (2)	0.029 (2)	0.0032 (18)	0.0004 (17)	0.0007 (18)
C13	0.054 (3)	0.050 (3)	0.045 (3)	−0.008 (2)	0.008 (2)	−0.008 (2)
C14	0.079 (4)	0.066 (3)	0.051 (3)	−0.003 (3)	0.011 (3)	−0.024 (3)
C15	0.066 (3)	0.077 (4)	0.041 (3)	0.008 (3)	0.015 (2)	−0.009 (3)
C16	0.049 (3)	0.071 (3)	0.039 (3)	0.005 (2)	0.008 (2)	0.005 (2)
C17	0.046 (3)	0.043 (2)	0.040 (2)	0.0046 (19)	0.000 (2)	−0.0013 (19)

Geometric parameters (Å, º) top

S1—O2	1.423 (2)	C9—C10	1.377 (5)
S1—O3	1.429 (3)	C11—C12	1.499 (5)
S1—N2	1.634 (3)	C12—C17	1.376 (5)
S1—C5	1.753 (4)	C12—C13	1.383 (5)
O1—N1	1.400 (5)	C13—C14	1.373 (6)
O1—C2	1.346 (6)	C14—C15	1.367 (6)
O4—C11	1.223 (4)	C15—C16	1.375 (6)
N1—C4	1.297 (6)	C16—C17	1.381 (5)
N2—C4	1.396 (5)	C1—H1A	0.9600
N3—C8	1.410 (4)	C1—H1B	0.9600
N3—C11	1.353 (5)	C1—H1C	0.9600
N2—H2N	0.8600	C3—H3	0.9300
N3—H3N	0.8600	C6—H6	0.9300
C1—C2	1.490 (7)	C7—H7	0.9300
C2—C3	1.322 (7)	C9—H9	0.9300
C3—C4	1.392 (6)	C10—H10	0.9300
C5—C10	1.377 (5)	C13—H13	0.9300
C5—C6	1.371 (5)	C14—H14	0.9300
C6—C7	1.367 (5)	C15—H15	0.9300
C7—C8	1.399 (5)	C16—H16	0.9300
C8—C9	1.374 (5)	C17—H17	0.9300

O2—S1—O3	119.92 (15)	C11—C12—C13	117.9 (3)
O2—S1—N2	107.63 (15)	C11—C12—C17	123.0 (3)
O2—S1—C5	108.46 (16)	C13—C12—C17	119.0 (3)
O3—S1—N2	104.41 (15)	C12—C13—C14	120.6 (4)
O3—S1—C5	108.76 (16)	C13—C14—C15	120.0 (4)
N2—S1—C5	106.94 (15)	C14—C15—C16	120.3 (4)
N1—O1—C2	108.9 (4)	C15—C16—C17	119.8 (4)
O1—N1—C4	104.0 (3)	C12—C17—C16	120.4 (4)
S1—N2—C4	122.7 (2)	C2—C1—H1A	109.00
C8—N3—C11	127.7 (3)	C2—C1—H1B	110.00
C4—N2—H2N	119.00	C2—C1—H1C	109.00
S1—N2—H2N	119.00	H1A—C1—H1B	109.00
C8—N3—H3N	116.00	H1A—C1—H1C	109.00
C11—N3—H3N	116.00	H1B—C1—H1C	109.00
C1—C2—C3	135.4 (5)	C2—C3—H3	128.00
O1—C2—C3	109.6 (4)	C4—C3—H3	128.00
O1—C2—C1	114.9 (5)	C5—C6—H6	120.00
C2—C3—C4	104.6 (4)	C7—C6—H6	120.00
N1—C4—N2	116.8 (4)	C6—C7—H7	120.00
N1—C4—C3	112.9 (4)	C8—C7—H7	120.00
N2—C4—C3	130.0 (4)	C8—C9—H9	120.00
S1—C5—C6	119.9 (3)	C10—C9—H9	119.00
S1—C5—C10	119.6 (3)	C5—C10—H10	120.00
C6—C5—C10	120.5 (3)	C9—C10—H10	120.00
C5—C6—C7	120.6 (3)	C12—C13—H13	120.00
C6—C7—C8	119.6 (3)	C14—C13—H13	120.00
N3—C8—C7	122.7 (3)	C13—C14—H14	120.00
N3—C8—C9	118.1 (3)	C15—C14—H14	120.00
C7—C8—C9	119.2 (3)	C14—C15—H15	120.00
C8—C9—C10	121.0 (3)	C16—C15—H15	120.00
C5—C10—C9	119.2 (3)	C15—C16—H16	120.00
O4—C11—C12	121.0 (3)	C17—C16—H16	120.00
N3—C11—C12	117.1 (3)	C12—C17—H17	120.00
O4—C11—N3	121.9 (3)	C16—C17—H17	120.00

O2—S1—N2—C4	−47.0 (3)	C2—C3—C4—N2	174.6 (4)
O3—S1—N2—C4	−175.5 (3)	S1—C5—C6—C7	179.4 (3)
C5—S1—N2—C4	69.4 (3)	C10—C5—C6—C7	−0.8 (5)
O2—S1—C5—C6	−167.7 (3)	S1—C5—C10—C9	−179.0 (3)
O2—S1—C5—C10	12.5 (3)	C6—C5—C10—C9	1.2 (5)
O3—S1—C5—C6	−35.7 (3)	C5—C6—C7—C8	−0.6 (5)
O3—S1—C5—C10	144.5 (3)	C6—C7—C8—N3	−176.3 (3)
N2—S1—C5—C6	76.5 (3)	C6—C7—C8—C9	1.5 (5)
N2—S1—C5—C10	−103.3 (3)	N3—C8—C9—C10	176.8 (3)
C2—O1—N1—C4	−0.4 (5)	C7—C8—C9—C10	−1.1 (6)
N1—O1—C2—C1	178.2 (4)	C8—C9—C10—C5	−0.2 (6)
N1—O1—C2—C3	0.8 (5)	O4—C11—C12—C13	−16.4 (5)
O1—N1—C4—N2	−175.0 (3)	O4—C11—C12—C17	159.5 (3)
O1—N1—C4—C3	0.0 (5)	N3—C11—C12—C13	165.4 (3)
S1—N2—C4—N1	−143.7 (3)	N3—C11—C12—C17	−18.7 (5)
S1—N2—C4—C3	42.4 (5)	C11—C12—C13—C14	175.7 (4)
C11—N3—C8—C7	−13.4 (6)	C17—C12—C13—C14	−0.4 (6)
C11—N3—C8—C9	168.7 (4)	C11—C12—C17—C16	−174.6 (3)
C8—N3—C11—O4	−11.1 (6)	C13—C12—C17—C16	1.2 (5)
C8—N3—C11—C12	167.0 (3)	C12—C13—C14—C15	−0.2 (7)
O1—C2—C3—C4	−0.7 (5)	C13—C14—C15—C16	−0.1 (7)
C1—C2—C3—C4	−177.5 (5)	C14—C15—C16—C17	0.9 (6)
C2—C3—C4—N1	0.5 (5)	C15—C16—C17—C12	−1.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4ⁱ	0.86	2.21	2.788 (4)	124
N3—H3N···O3ⁱⁱ	0.86	2.27	3.075 (4)	156
C7—H7···O4	0.93	2.26	2.832 (4)	119
C10—H10···O2ⁱⁱⁱ	0.93	2.44	3.130 (4)	131

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃O₄S
M_r	357.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.2407 (6), 23.5069 (16), 8.5199 (6)
β (°)	92.155 (3)
V (Å³)	1649.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.34 × 0.17 × 0.07

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12756, 2865, 1544
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.135, 0.99
No. of reflections	2865
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4ⁱ	0.86	2.21	2.788 (4)	124
N3—H3N···O3ⁱⁱ	0.86	2.27	3.075 (4)	156
C7—H7···O4	0.93	2.26	2.832 (4)	119
C10—H10···O2ⁱⁱⁱ	0.93	2.44	3.130 (4)	131

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

Footnotes

‡Additional corresponding author, e-mail: iukhan.gcu@gmail.com.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

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