3-[4-(Acetamido)­benzene­sulfonamido]­benzoic acid

Mirza, S.M.; Mustafa, G.; Khan, I.U.; Zia-ur-Rehman, M.; Shafiq, M.

doi:10.1107/S1600536810048397

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages o25-o26

https://doi.org/10.1107/S1600536810048397

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3-[4-(Acetamido)benzenesulfonamido]benzoic acid

Sidra Muzaffar Mirza,^a Ghulam Mustafa,^a Islam Ullah Khan,^a Muhammad Zia-ur-Rehman ^b ^* and Muhammad Shafiq ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan
^*Correspondence e-mail: rehman_pcsir@hotmail.com

(Received 9 November 2010; accepted 20 November 2010; online 4 December 2010)

In the title compound, C₁₅H₁₄N₂O₅S, the dihedral angle between the aromatic rings is 63.20 (11) Å. The crystal structure displays classical intermolecular O—H⋯O hydrogen bonding typical for carboxylic acids, forming centrosymmetric dimers. These dimers are further connected by N—H⋯O and C—H⋯O hydrogen bonds to form an extended network.

Related literature

For the synthesis of related compounds, see: Khan et al. (2009 ); Arshad et al. (2008 ). For the biological activity of sulfonamides, see: Esteve & Bidal (2002 ); Hanson et al. (1999 ); Lee & Lee (2002 ); Moree et al. (1991 ); Ozbek et al. (2007 ); Parari et al. (2008 ); Ratish et al. (2009 ); Rough et al. (1998 ); Selnam et al. (2001 ); Soledade et al. (2006 ); Xiao & Timberlake (2000 ). For related structures, see: Gowda et al. (2007a ,b ,c ); Haider et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₅S
M_r = 334.34
Triclinic, $[P \overline 1]$
a = 7.9829 (3) Å
b = 8.4143 (3) Å
c = 12.6554 (5) Å
α = 70.888 (2)°
β = 81.553 (2)°
γ = 77.104 (2)°
V = 780.44 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.24 × 0.18 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
13620 measured reflections
3835 independent reflections
2928 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.150
S = 1.02
3835 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H7⋯O4ⁱ	0.88	1.74	2.617 (4)	170
N1—H1⋯O16ⁱⁱ	0.86	2.31	2.860 (2)	122
N3—H3⋯O1ⁱⁱⁱ	0.86	2.13	2.974 (2)	165
C11—H11⋯O2^iv	0.93	2.59	3.379 (3)	143
Symmetry codes: (i) -x-1, -y+2, -z+1; (ii) -x, -y+2, -z; (iii) x, y+1, z; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048397/sj5052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048397/sj5052Isup2.hkl

checkCIF report

Comment top

Sulfonamides are well known in literature for their potential as biologically active compounds (Hanson et al., 1999; Moree et al.,1991; Rough et al., 1998). These have been reported to display anti-hypertensive, anti-convulsant, herbicidal and anti-malarial activities (Esteve & Bidal, 2002; Soledade et al., 2006; Xiao & Timberlake, 2000; Lee & Lee, 2002). In addition the sulfonamide unit has been found in a number of compounds possessing anti-HIV (Selnam et al.,2001), anti-inflammatory (Ratish et al., 2009) and anti-microbial (Ozbek et al., 2007; Parari et al., 2008) activities.

In continuation of our work regarding the synthesis of various sulfur containing heterocycles (Arshad et al., 2008; Khan et al., 2009), the structure of 3-({[4-(acetylamino)phenyl]sulfonyl}amino)benzoic acid (I) has been determined. Bond lengths and bond angles of the title molecule (Fig 1) are similar to those in related compounds (Gowda et al., 2007a,b,c; Haider et al., 2009) and are within normal ranges (Allen et al., 1987). In the crystal structure, each molecule is linked to an adjacent one through classical O5—H7···O4 intermolecular hydrogen bonds forming centrosymmetric dimers typical of carboxylic acids, Table 1. These dimers are further connected by N—H···O and C—H···O hydrogen bonds to form an extended network, Fig 2.

Related literature top

For the synthesis of related compounds, see: Khan et al. (2009); Arshad et al. (2008). For the biological activity of sulfonamides, see: Esteve & Bidal (2002); Hanson et al. (1999); Lee & Lee (2002); Moree et al. (1991); Ozbek et al. (2007); Parari et al. (2008); Ratish et al. (2009); Rough et al. (1998); Selnam et al. (2001); Soledade et al. (2006); Xiao & Timberlake (2000). For related structures, see: Gowda et al. (2007a,b,c); Haider et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

To an aqueous solution (10.0 ml) of 4-amino benzoic acid (1.0 g; 7.3 mmoles) maintained at pH 9 with aqueous sodium bicarbonate solution, 4-(acetylamino)benzenesulfonyl chloride (2.21 g, 9.48 mmol) was added. Contents were stirred at room temperature until the complete consumption of the sulfonyl chloride (as indicated by TLC). The pH of the reaction mixture was changed to 1 using hydrochloric acid (1 M) and the precipitate obtained was filtered, washed with water and dried. The resulting solid was recrystallized from methanol to get suitable crystals.

Structure description top

For the synthesis of related compounds, see: Khan et al. (2009); Arshad et al. (2008). For the biological activity of sulfonamides, see: Esteve & Bidal (2002); Hanson et al. (1999); Lee & Lee (2002); Moree et al. (1991); Ozbek et al. (2007); Parari et al. (2008); Ratish et al. (2009); Rough et al. (1998); Selnam et al. (2001); Soledade et al. (2006); Xiao & Timberlake (2000). For related structures, see: Gowda et al. (2007a,b,c); Haider et al. (2009). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Perspective view of the three-dimensional crystal packing showing hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

3-[4-(Acetamido)benzenesulfonamido]benzoic acid top

Crystal data top

C₁₅H₁₄N₂O₅S	Z = 2
M_r = 334.34	F(000) = 348
Triclinic, P1	D_x = 1.423 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9829 (3) Å	Cell parameters from 5086 reflections
b = 8.4143 (3) Å	θ = 2.6–27.5°
c = 12.6554 (5) Å	µ = 0.23 mm⁻¹
α = 70.888 (2)°	T = 296 K
β = 81.553 (2)°	Needles, dark brown
γ = 77.104 (2)°	0.24 × 0.18 × 0.14 mm
V = 780.44 (5) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	2928 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 28.3°, θ_min = 2.7°
φ and ω scans	h = −9→10
13620 measured reflections	k = −10→11
3835 independent reflections	l = −16→16

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) = 0.150	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0733P)² + 0.3675P] where P = (F_o² + 2F_c²)/3
3835 reflections	(Δ/σ)_max = 0.034
210 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₅S	γ = 77.104 (2)°
M_r = 334.34	V = 780.44 (5) Å³
Triclinic, P1	Z = 2
a = 7.9829 (3) Å	Mo Kα radiation
b = 8.4143 (3) Å	µ = 0.23 mm⁻¹
c = 12.6554 (5) Å	T = 296 K
α = 70.888 (2)°	0.24 × 0.18 × 0.14 mm
β = 81.553 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2928 reflections with I > 2σ(I)
13620 measured reflections	R_int = 0.032
3835 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.02	Δρ_max = 0.49 e Å⁻³
3835 reflections	Δρ_min = −0.47 e Å⁻³
210 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	0.36529 (6)	0.60917 (7)	0.20813 (4)	0.03843 (18)
N1	0.1928 (2)	0.5659 (2)	0.28924 (14)	0.0397 (4)
H1	0.1346	0.4996	0.2775	0.048*
O2	0.50673 (18)	0.5656 (2)	0.27558 (14)	0.0503 (4)
O1	0.3732 (2)	0.5277 (2)	0.12378 (13)	0.0489 (4)
C4	0.2682 (3)	1.1815 (3)	0.03783 (17)	0.0380 (5)
C1	0.3286 (2)	0.8313 (3)	0.14368 (17)	0.0373 (4)
N3	0.2462 (2)	1.3587 (2)	−0.01344 (14)	0.0424 (4)
H3	0.2964	1.4127	0.0158	0.051*
O16	0.0723 (2)	1.3984 (2)	−0.14922 (15)	0.0601 (5)
C7	0.1369 (3)	0.6366 (3)	0.37967 (17)	0.0370 (4)
O5	−0.3233 (3)	0.9184 (3)	0.57458 (17)	0.0786 (7)
C14	0.1564 (3)	1.4568 (3)	−0.10295 (18)	0.0421 (5)
O4	−0.3591 (3)	0.9200 (4)	0.40422 (19)	0.0954 (9)
C9	−0.0886 (3)	0.7910 (3)	0.47573 (18)	0.0437 (5)
C12	0.2427 (3)	0.6086 (3)	0.46374 (19)	0.0511 (6)
H12	0.3535	0.5447	0.4610	0.061*
C8	−0.0291 (3)	0.7287 (3)	0.38531 (18)	0.0411 (5)
H8	−0.1007	0.7490	0.3288	0.049*
C10	0.0194 (3)	0.7651 (3)	0.5583 (2)	0.0530 (6)
H10	−0.0194	0.8083	0.6182	0.064*
C11	0.1851 (3)	0.6745 (4)	0.5510 (2)	0.0593 (7)
H11	0.2586	0.6580	0.6058	0.071*
C15	0.1669 (3)	1.6414 (3)	−0.1392 (2)	0.0518 (6)
H15A	0.0989	1.7018	−0.2019	0.078*
H15B	0.2847	1.6541	−0.1608	0.078*
H15C	0.1237	1.6877	−0.0784	0.078*
C6	0.2468 (5)	0.9002 (4)	0.0475 (3)	0.0854 (11)
H6	0.2102	0.8281	0.0172	0.102*
C5	0.2170 (5)	1.0723 (4)	−0.0058 (3)	0.0823 (11)
H5	0.1618	1.1157	−0.0720	0.099*
C13	−0.2682 (3)	0.8827 (4)	0.4850 (2)	0.0570 (7)
C2	0.3792 (5)	0.9385 (4)	0.1877 (2)	0.0757 (10)
H2	0.4357	0.8940	0.2533	0.091*
C3	0.3476 (5)	1.1122 (4)	0.1358 (2)	0.0760 (10)
H4	0.3807	1.1841	0.1679	0.091*
H7	−0.4296	0.9779	0.5730	0.30 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0298 (3)	0.0460 (3)	0.0443 (3)	−0.0019 (2)	−0.0027 (2)	−0.0237 (2)
N1	0.0351 (9)	0.0448 (10)	0.0441 (10)	−0.0086 (7)	−0.0023 (7)	−0.0196 (8)
O2	0.0323 (8)	0.0616 (10)	0.0597 (10)	0.0010 (7)	−0.0102 (7)	−0.0257 (8)
O1	0.0472 (9)	0.0552 (10)	0.0543 (9)	−0.0056 (7)	0.0007 (7)	−0.0346 (8)
C4	0.0325 (10)	0.0502 (12)	0.0366 (10)	−0.0100 (9)	−0.0007 (8)	−0.0199 (9)
C1	0.0319 (9)	0.0462 (12)	0.0393 (11)	−0.0091 (8)	0.0007 (8)	−0.0208 (9)
N3	0.0442 (10)	0.0486 (11)	0.0414 (10)	−0.0124 (8)	−0.0087 (8)	−0.0185 (8)
O16	0.0570 (10)	0.0703 (12)	0.0606 (11)	−0.0117 (9)	−0.0257 (8)	−0.0210 (9)
C7	0.0352 (10)	0.0405 (11)	0.0341 (10)	−0.0052 (8)	−0.0019 (8)	−0.0112 (9)
O5	0.0565 (11)	0.1177 (18)	0.0653 (12)	0.0201 (11)	−0.0089 (9)	−0.0554 (12)
C14	0.0339 (10)	0.0570 (13)	0.0385 (11)	−0.0055 (9)	0.0001 (8)	−0.0221 (10)
O4	0.0579 (12)	0.156 (2)	0.0790 (14)	0.0398 (13)	−0.0287 (11)	−0.0740 (15)
C9	0.0404 (11)	0.0497 (13)	0.0409 (12)	−0.0025 (9)	−0.0047 (9)	−0.0169 (10)
C12	0.0372 (11)	0.0699 (16)	0.0423 (12)	0.0038 (11)	−0.0099 (9)	−0.0182 (11)
C8	0.0372 (10)	0.0485 (12)	0.0376 (11)	−0.0019 (9)	−0.0089 (8)	−0.0146 (9)
C10	0.0522 (13)	0.0692 (16)	0.0402 (12)	−0.0033 (12)	−0.0059 (10)	−0.0244 (12)
C11	0.0489 (13)	0.089 (2)	0.0423 (13)	−0.0005 (13)	−0.0159 (10)	−0.0255 (13)
C15	0.0544 (14)	0.0541 (14)	0.0452 (13)	−0.0014 (11)	−0.0027 (10)	−0.0190 (11)
C6	0.130 (3)	0.0517 (16)	0.096 (2)	−0.0114 (17)	−0.075 (2)	−0.0271 (15)
C5	0.129 (3)	0.0534 (16)	0.080 (2)	−0.0076 (17)	−0.071 (2)	−0.0206 (14)
C13	0.0486 (13)	0.0706 (17)	0.0553 (15)	0.0080 (12)	−0.0088 (11)	−0.0347 (13)
C2	0.128 (3)	0.0570 (16)	0.0561 (16)	−0.0268 (17)	−0.0497 (17)	−0.0113 (13)
C3	0.129 (3)	0.0529 (15)	0.0634 (17)	−0.0294 (17)	−0.0507 (18)	−0.0142 (13)

Geometric parameters (Å, º) top

S1—O2	1.4252 (15)	O4—C13	1.255 (3)
S1—O1	1.4331 (15)	C9—C10	1.383 (3)
S1—N1	1.6264 (17)	C9—C8	1.390 (3)
S1—C1	1.753 (2)	C9—C13	1.477 (3)
N1—C7	1.428 (2)	C12—C11	1.369 (3)
N1—H1	0.8600	C12—H12	0.9300
C4—C3	1.368 (3)	C8—H8	0.9300
C4—C5	1.372 (3)	C10—C11	1.378 (4)
C4—N3	1.399 (3)	C10—H10	0.9300
C1—C2	1.359 (3)	C11—H11	0.9300
C1—C6	1.359 (3)	C15—H15A	0.9600
N3—C14	1.357 (3)	C15—H15B	0.9600
N3—H3	0.8600	C15—H15C	0.9600
O16—C14	1.219 (3)	C6—C5	1.365 (4)
C7—C8	1.383 (3)	C6—H6	0.9300
C7—C12	1.383 (3)	C5—H5	0.9300
O5—C13	1.260 (3)	C2—C3	1.374 (4)
O5—H7	0.8831	C2—H2	0.9300
C14—C15	1.487 (3)	C3—H4	0.9300

O2—S1—O1	119.27 (9)	C7—C8—C9	119.82 (19)
O2—S1—N1	108.91 (9)	C7—C8—H8	120.1
O1—S1—N1	105.07 (9)	C9—C8—H8	120.1
O2—S1—C1	107.95 (10)	C11—C10—C9	119.4 (2)
O1—S1—C1	108.32 (10)	C11—C10—H10	120.3
N1—S1—C1	106.68 (9)	C9—C10—H10	120.3
C7—N1—S1	120.87 (14)	C12—C11—C10	120.6 (2)
C7—N1—H1	119.6	C12—C11—H11	119.7
S1—N1—H1	119.6	C10—C11—H11	119.7
C3—C4—C5	117.9 (2)	C14—C15—H15A	109.5
C3—C4—N3	118.54 (19)	C14—C15—H15B	109.5
C5—C4—N3	123.5 (2)	H15A—C15—H15B	109.5
C2—C1—C6	118.4 (2)	C14—C15—H15C	109.5
C2—C1—S1	121.67 (18)	H15A—C15—H15C	109.5
C6—C1—S1	119.95 (17)	H15B—C15—H15C	109.5
C14—N3—C4	128.83 (18)	C1—C6—C5	121.8 (2)
C14—N3—H3	115.6	C1—C6—H6	119.1
C4—N3—H3	115.6	C5—C6—H6	119.1
C8—C7—C12	119.55 (19)	C6—C5—C4	120.2 (2)
C8—C7—N1	119.05 (18)	C6—C5—H5	119.9
C12—C7—N1	121.34 (19)	C4—C5—H5	119.9
C13—O5—H7	113.2	O4—C13—O5	123.1 (2)
O16—C14—N3	122.6 (2)	O4—C13—C9	118.9 (2)
O16—C14—C15	122.7 (2)	O5—C13—C9	118.0 (2)
N3—C14—C15	114.73 (19)	C1—C2—C3	120.4 (2)
C10—C9—C8	120.1 (2)	C1—C2—H2	119.8
C10—C9—C13	119.8 (2)	C3—C2—H2	119.8
C8—C9—C13	120.1 (2)	C4—C3—C2	121.2 (2)
C11—C12—C7	120.4 (2)	C4—C3—H4	119.4
C11—C12—H12	119.8	C2—C3—H4	119.4
C7—C12—H12	119.8

O2—S1—N1—C7	55.28 (18)	C13—C9—C8—C7	−177.2 (2)
O1—S1—N1—C7	−175.87 (15)	C8—C9—C10—C11	−1.1 (4)
C1—S1—N1—C7	−60.99 (17)	C13—C9—C10—C11	177.9 (3)
O2—S1—C1—C2	−23.6 (3)	C7—C12—C11—C10	2.0 (4)
O1—S1—C1—C2	−154.0 (2)	C9—C10—C11—C12	−0.8 (4)
N1—S1—C1—C2	93.4 (2)	C2—C1—C6—C5	0.8 (5)
O2—S1—C1—C6	156.7 (2)	S1—C1—C6—C5	−179.4 (3)
O1—S1—C1—C6	26.3 (3)	C1—C6—C5—C4	−0.7 (6)
N1—S1—C1—C6	−86.4 (3)	C3—C4—C5—C6	−0.6 (5)
C3—C4—N3—C14	−172.3 (3)	N3—C4—C5—C6	178.3 (3)
C5—C4—N3—C14	8.9 (4)	C10—C9—C13—O4	173.0 (3)
S1—N1—C7—C8	124.75 (19)	C8—C9—C13—O4	−8.0 (4)
S1—N1—C7—C12	−57.9 (3)	C10—C9—C13—O5	−7.6 (4)
C4—N3—C14—O16	3.6 (3)	C8—C9—C13—O5	171.4 (3)
C4—N3—C14—C15	−177.18 (19)	C6—C1—C2—C3	0.2 (5)
C8—C7—C12—C11	−1.3 (4)	S1—C1—C2—C3	−179.5 (3)
N1—C7—C12—C11	−178.6 (2)	C5—C4—C3—C2	1.6 (5)
C12—C7—C8—C9	−0.6 (3)	N3—C4—C3—C2	−177.3 (3)
N1—C7—C8—C9	176.8 (2)	C1—C2—C3—C4	−1.5 (5)
C10—C9—C8—C7	1.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H7···O4ⁱ	0.88	1.74	2.617 (4)	170
N1—H1···O16ⁱⁱ	0.86	2.31	2.860 (2)	122
N3—H3···O1ⁱⁱⁱ	0.86	2.13	2.974 (2)	165
C11—H11···O2^iv	0.93	2.59	3.379 (3)	143

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₅S
M_r	334.34
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.9829 (3), 8.4143 (3), 12.6554 (5)
α, β, γ (°)	70.888 (2), 81.553 (2), 77.104 (2)
V (Å³)	780.44 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.24 × 0.18 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13620, 3835, 2928
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.150, 1.02
No. of reflections	3835
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.47

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H7···O4ⁱ	0.88	1.74	2.617 (4)	170
N1—H1···O16ⁱⁱ	0.86	2.31	2.860 (2)	122
N3—H3···O1ⁱⁱⁱ	0.86	2.13	2.974 (2)	165
C11—H11···O2^iv	0.93	2.59	3.379 (3)	143

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

Acknowledgements

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

References

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