Cyano­methyl 4-(4-methyl­benzene­sulfonamido)­benzoate

Mustafa, G.; Akkurt, M.; Khan, I.U.; Muhmood, T.

doi:10.1107/S1600536812017126

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1488

doi:10.1107/S1600536812017126

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Cyanomethyl 4-(4-methylbenzenesulfonamido)benzoate

Ghulam Mustafa,^a ^* Mehmet Akkurt,^b ^* Islam Ullah Khan ^a and Tahir Muhmood ^a

^aDepartment of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: gmustafa884@yahoo.com, akkurt@erciyes.edu.tr

(Received 10 April 2012; accepted 18 April 2012; online 21 April 2012)

The title molecule, C₁₆H₁₄N₂O₄S, adopts an L-shaped conformation, with the central C—S—N—C torsion angle being −69.1 (3)°. The two benzene rings form a dihedral angle of 89.94 (15)°. The molecular conformation may be influenced by a weak intramolecular C—H⋯O hydrogen bond which generates an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O and weak C—H⋯O hydrogen bonds, forming chains propagating along the b axis. Weak C—H⋯N hydrogen bonds connect the chains into a two-dimensional network parallel to (011). The crystal studied was an inversion twin, the ratio of components being 0.7 (1):0.3 (1).

Related literature

For related structures, see: Mustafa et al. (2010 , 2011 , 2012a ,b ); Khan et al. (2011 ). For standard bond-length data, see: Allen et al. (1987 ). For hydrogen bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₄S
M_r = 330.36
Monoclinic, P 2₁
a = 5.9360 (3) Å
b = 8.1992 (4) Å
c = 15.9068 (8) Å
β = 91.222 (3)°
V = 774.02 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.28 × 0.23 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
6266 measured reflections
3077 independent reflections
2306 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.106
S = 1.01
3077 reflections
210 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1248 Freidel pairs
Flack parameter: 0.30 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.21	2.904 (3)	138
C1—H1A⋯O2ⁱⁱ	0.96	2.58	3.446 (5)	150
C9—H9⋯O2	0.93	2.38	3.025 (4)	126
C10—H10⋯O1ⁱⁱⁱ	0.93	2.51	3.431 (4)	172
C12—H12⋯N2^iv	0.93	2.62	3.426 (6)	146
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) x, y-1, z; (iv) $[-x-1, y+{\script{1\over 2}}, -z]$ .

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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812017126/lh5455sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017126/lh5455Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017126/lh5455Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of sulfonamides with potential biological properties (Mustafa et al., 2010, 2011, 2012a,b; Khan et al., 2011), the crystal structure of the title compound (I) has been determined.

The molecular structure of (I) (Fig. 1), has a L-shaped conformation, with the central C5—S1—N1—C8 torsion angle being -69.1 (3)°. The two benzene rings (C2—C7) and (C8—C13) are nearly perpendicular to each other, with a dihedral angle of 89.94 (15)°. All the bond lengths (Allen et al., 1987) and angles are normal (Mustafa et al., 2010; 2011, 2012a,b; Khan et al., 2011).

The title molecule exhibits an S(6) motif (Bernstein et al., 1995) formed by a weak intramolecular C—H···O hydrogen bond interaction (Table 1). In the crystal, molecules are linked by N—H···O and weak C—H···O hydrogen bonds forming chains propagating along the b axis. Weak intermolecular C—H···N hydrogen bonds connect the chains into a two dimensional netwok (Table 1, Fig. 2).

Related literature top

For related structures, see: Mustafa et al. (2010, 2011, 2012a,b); Khan et al. (2011). For standard bond-length data, see: Allen et al. (1987). For hydrogen bond motifs, see: Bernstein et al. (1995).

Experimental top

To an aquious solution of p-amino benzoic acid (1.0 g, 7.3 mmol), sodium carbonate (1 N) was added to adjust the pH to 8. Then p-toluenesulfonyl chloride (1.80 g, 9.48 mmol) was added and the mixture was stirred at room temperature keeping the pH of the mixture at 8.0 with occasional addition of sodium carbonate solution. Progress and completion of the reaction was confirmed by TLC and conversion of the suspension into a clear solution. After 2 h, whole mixture was poured into a beaker and the pH was adjusted to 2.0 by 1 N HCl. Pprecipitates were produced which were filtered and washed with distilled water.

The prepared sulfonamide (4-(Toluene-4-sulfonylamino)-benzoic acid) (1.0 g, 3.43 mmol), DMF (10 ml) and n-hexane washed sodium hydride (0.25 g, 10.31 mmol) were stirred at room temperature for 40 min followed by the addition of chloroacetonitrile (0.34 g, 4.46 mmol). The whole reaction mixture was stirred at 353 K till the completion of the reaction and poured into crushed ice in a beaker. The pH of the mixture was adjusted to 4.0 with 1 N HCl. Precipitates were produced, filtered and washed twice with distilled water. Crystals suitable for X-ray diffraction were grown from a chloroform solution of the title compound.

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. View of the packing and hydrogen-bonding interactions in (I) The hydrogen atoms not involved in the hydrogen bonds have been omitted.

Cyanomethyl 4-(4-methylbenzenesulfonamido)benzoate top

Crystal data top

C₁₆H₁₄N₂O₄S	F(000) = 344
M_r = 330.36	D_x = 1.418 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2045 reflections
a = 5.9360 (3) Å	θ = 2.6–24.7°
b = 8.1992 (4) Å	µ = 0.23 mm⁻¹
c = 15.9068 (8) Å	T = 296 K
β = 91.222 (3)°	Block, yellow
V = 774.02 (7) Å³	0.28 × 0.23 × 0.19 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	2306 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 27.1°, θ_min = 1.3°
ϕ and ω scans	h = −7→7
6266 measured reflections	k = −8→10
3077 independent reflections	l = −20→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0538P)² + 0.0338P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3077 reflections	Δρ_max = 0.20 e Å⁻³
210 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1248 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.30 (10)

Crystal data top

C₁₆H₁₄N₂O₄S	V = 774.02 (7) Å³
M_r = 330.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.9360 (3) Å	µ = 0.23 mm⁻¹
b = 8.1992 (4) Å	T = 296 K
c = 15.9068 (8) Å	0.28 × 0.23 × 0.19 mm
β = 91.222 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2306 reflections with I > 2σ(I)
6266 measured reflections	R_int = 0.027
3077 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.106	Δρ_max = 0.20 e Å⁻³
S = 1.01	Δρ_min = −0.25 e Å⁻³
3077 reflections	Absolute structure: Flack (1983), 1248 Freidel pairs
210 parameters	Absolute structure parameter: 0.30 (10)
1 restraint

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	0.58175 (11)	0.32017 (11)	0.30134 (5)	0.0453 (2)
O1	0.6354 (4)	0.4862 (3)	0.28356 (14)	0.0570 (8)
O2	0.7581 (3)	0.2041 (3)	0.31249 (15)	0.0597 (9)
O3	0.1129 (4)	−0.4816 (3)	0.16303 (18)	0.0630 (10)
O4	−0.1469 (4)	−0.3362 (3)	0.09421 (15)	0.0576 (8)
N1	0.4185 (4)	0.2648 (3)	0.22249 (17)	0.0505 (9)
N2	−0.6118 (7)	−0.3907 (7)	−0.0148 (3)	0.1056 (19)
C1	0.0250 (6)	0.3400 (6)	0.6140 (2)	0.0774 (14)
C2	0.1617 (5)	0.3314 (5)	0.53585 (18)	0.0512 (10)
C3	0.3637 (6)	0.2464 (4)	0.5345 (2)	0.0595 (12)
C4	0.4901 (5)	0.2381 (4)	0.4627 (2)	0.0515 (11)
C5	0.4149 (4)	0.3166 (4)	0.39131 (16)	0.0400 (8)
C6	0.2138 (5)	0.4021 (4)	0.3910 (2)	0.0487 (11)
C7	0.0899 (5)	0.4073 (4)	0.4624 (2)	0.0542 (11)
C8	0.3266 (5)	0.1077 (4)	0.20785 (18)	0.0422 (10)
C9	0.4346 (5)	−0.0359 (4)	0.2306 (2)	0.0538 (11)
C10	0.3380 (4)	−0.1827 (5)	0.20995 (18)	0.0508 (9)
C11	0.1348 (4)	−0.1913 (5)	0.16607 (16)	0.0416 (8)
C12	0.0272 (5)	−0.0468 (4)	0.1442 (2)	0.0466 (11)
C13	0.1211 (5)	0.0997 (4)	0.1656 (2)	0.0484 (11)
C14	0.0402 (5)	−0.3518 (4)	0.1432 (2)	0.0481 (11)
C15	−0.2527 (6)	−0.4841 (4)	0.0670 (2)	0.0621 (12)
C16	−0.4543 (8)	−0.4347 (5)	0.0209 (3)	0.0704 (17)
H1	0.38520	0.33880	0.18600	0.0610*
H1A	0.02430	0.45000	0.63460	0.1160*
H1B	0.08990	0.26940	0.65610	0.1160*
H1C	−0.12670	0.30610	0.60120	0.1160*
H3	0.41510	0.19380	0.58310	0.0710*
H4	0.62470	0.18000	0.46270	0.0620*
H6	0.16340	0.45560	0.34250	0.0590*
H7	−0.04630	0.46340	0.46160	0.0650*
H9	0.57210	−0.03270	0.25960	0.0640*
H10	0.41080	−0.27870	0.22580	0.0610*
H12	−0.10980	−0.04980	0.11480	0.0560*
H13	0.04560	0.19560	0.15150	0.0580*
H15A	−0.29080	−0.55120	0.11490	0.0740*
H15B	−0.15360	−0.54570	0.03110	0.0740*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0447 (3)	0.0424 (4)	0.0486 (4)	−0.0002 (4)	−0.0010 (3)	−0.0054 (4)
O1	0.0656 (14)	0.0481 (15)	0.0572 (15)	−0.0175 (12)	0.0007 (11)	0.0017 (11)
O2	0.0456 (12)	0.0650 (16)	0.0684 (17)	0.0109 (12)	−0.0035 (12)	−0.0136 (13)
O3	0.0728 (17)	0.0376 (14)	0.078 (2)	0.0009 (12)	−0.0101 (15)	0.0073 (13)
O4	0.0626 (13)	0.0432 (13)	0.0662 (16)	−0.0060 (11)	−0.0166 (11)	−0.0016 (12)
N1	0.0686 (16)	0.0394 (17)	0.0430 (16)	−0.0007 (12)	−0.0077 (13)	−0.0001 (11)
N2	0.080 (3)	0.147 (4)	0.089 (3)	−0.016 (3)	−0.017 (2)	−0.030 (3)
C1	0.081 (2)	0.087 (3)	0.065 (2)	−0.032 (3)	0.0211 (18)	−0.016 (3)
C2	0.0556 (16)	0.0490 (19)	0.0493 (18)	−0.0153 (19)	0.0056 (13)	−0.012 (2)
C3	0.069 (2)	0.060 (2)	0.049 (2)	−0.0071 (17)	−0.0092 (17)	0.0152 (16)
C4	0.0490 (16)	0.0492 (19)	0.056 (2)	0.0085 (15)	−0.0042 (16)	0.0071 (16)
C5	0.0401 (12)	0.0322 (13)	0.0473 (15)	0.0002 (17)	−0.0056 (11)	−0.0017 (18)
C6	0.0481 (17)	0.0507 (18)	0.047 (2)	0.0090 (16)	−0.0053 (15)	0.0056 (15)
C7	0.0441 (16)	0.0535 (19)	0.065 (2)	0.0053 (16)	0.0008 (16)	−0.0030 (18)
C8	0.0480 (16)	0.0437 (19)	0.0352 (17)	0.0022 (15)	0.0048 (13)	−0.0013 (14)
C9	0.0486 (17)	0.051 (2)	0.061 (2)	0.0068 (16)	−0.0147 (16)	−0.0020 (17)
C10	0.0517 (14)	0.0448 (17)	0.0554 (18)	0.011 (2)	−0.0074 (13)	0.002 (2)
C11	0.0458 (12)	0.0407 (16)	0.0383 (15)	0.0018 (18)	0.0024 (11)	0.0028 (17)
C12	0.0435 (17)	0.047 (2)	0.049 (2)	0.0035 (15)	−0.0040 (15)	−0.0004 (16)
C13	0.0458 (17)	0.044 (2)	0.055 (2)	0.0056 (16)	−0.0082 (17)	−0.0011 (18)
C14	0.0471 (17)	0.048 (2)	0.049 (2)	−0.0018 (17)	−0.0003 (16)	−0.0013 (18)
C15	0.072 (2)	0.057 (2)	0.057 (2)	−0.0181 (19)	−0.0040 (19)	−0.0070 (18)
C16	0.066 (3)	0.095 (3)	0.050 (3)	−0.018 (2)	−0.0030 (19)	−0.015 (2)

Geometric parameters (Å, º) top

S1—O1	1.428 (3)	C9—C10	1.370 (5)
S1—O2	1.423 (2)	C10—C11	1.382 (3)
S1—N1	1.633 (3)	C11—C12	1.387 (5)
S1—C5	1.758 (3)	C11—C14	1.473 (5)
O3—C14	1.189 (4)	C12—C13	1.364 (5)
O4—C14	1.349 (4)	C15—C16	1.448 (6)
O4—C15	1.429 (4)	C1—H1A	0.9600
N1—C8	1.416 (4)	C1—H1B	0.9600
N2—C16	1.142 (7)	C1—H1C	0.9600
N1—H1	0.8600	C3—H3	0.9300
C1—C2	1.501 (4)	C4—H4	0.9300
C2—C7	1.383 (4)	C6—H6	0.9300
C2—C3	1.388 (5)	C7—H7	0.9300
C3—C4	1.382 (5)	C9—H9	0.9300
C4—C5	1.372 (4)	C10—H10	0.9300
C5—C6	1.384 (4)	C12—H12	0.9300
C6—C7	1.367 (4)	C13—H13	0.9300
C8—C9	1.385 (5)	C15—H15A	0.9700
C8—C13	1.382 (4)	C15—H15B	0.9700

O1—S1—O2	119.72 (14)	O3—C14—O4	121.9 (3)
O1—S1—N1	104.13 (14)	O4—C14—C11	111.3 (3)
O1—S1—C5	108.00 (15)	O4—C15—C16	105.6 (3)
O2—S1—N1	109.43 (14)	N2—C16—C15	177.8 (5)
O2—S1—C5	108.25 (14)	C2—C1—H1A	109.00
N1—S1—C5	106.57 (13)	C2—C1—H1B	109.00
C14—O4—C15	116.5 (3)	C2—C1—H1C	109.00
S1—N1—C8	126.8 (2)	H1A—C1—H1B	109.00
S1—N1—H1	117.00	H1A—C1—H1C	109.00
C8—N1—H1	117.00	H1B—C1—H1C	110.00
C3—C2—C7	117.6 (3)	C2—C3—H3	119.00
C1—C2—C3	121.3 (3)	C4—C3—H3	119.00
C1—C2—C7	121.1 (3)	C3—C4—H4	120.00
C2—C3—C4	121.5 (3)	C5—C4—H4	120.00
C3—C4—C5	119.2 (3)	C5—C6—H6	120.00
S1—C5—C6	119.3 (2)	C7—C6—H6	120.00
S1—C5—C4	120.2 (2)	C2—C7—H7	119.00
C4—C5—C6	120.4 (3)	C6—C7—H7	119.00
C5—C6—C7	119.5 (3)	C8—C9—H9	120.00
C2—C7—C6	121.8 (3)	C10—C9—H9	120.00
C9—C8—C13	119.1 (3)	C9—C10—H10	119.00
N1—C8—C13	117.1 (3)	C11—C10—H10	119.00
N1—C8—C9	123.8 (3)	C11—C12—H12	120.00
C8—C9—C10	119.7 (3)	C13—C12—H12	120.00
C9—C10—C11	121.5 (3)	C8—C13—H13	120.00
C12—C11—C14	122.0 (2)	C12—C13—H13	119.00
C10—C11—C12	118.4 (3)	O4—C15—H15A	111.00
C10—C11—C14	119.6 (3)	O4—C15—H15B	111.00
C11—C12—C13	120.4 (3)	C16—C15—H15A	111.00
C8—C13—C12	121.0 (3)	C16—C15—H15B	111.00
O3—C14—C11	126.9 (3)	H15A—C15—H15B	109.00

O1—S1—N1—C8	176.9 (2)	C3—C4—C5—C6	−0.5 (5)
O2—S1—N1—C8	47.8 (3)	C3—C4—C5—S1	175.5 (3)
C5—S1—N1—C8	−69.1 (3)	C4—C5—C6—C7	−0.2 (5)
O1—S1—C5—C4	−118.0 (3)	S1—C5—C6—C7	−176.3 (2)
O2—S1—C5—C4	13.0 (3)	C5—C6—C7—C2	1.1 (5)
N1—S1—C5—C4	130.6 (3)	N1—C8—C13—C12	175.8 (3)
O1—S1—C5—C6	58.1 (3)	C9—C8—C13—C12	−1.8 (5)
O2—S1—C5—C6	−171.0 (2)	N1—C8—C9—C10	−176.6 (3)
N1—S1—C5—C6	−53.3 (3)	C13—C8—C9—C10	0.9 (4)
C15—O4—C14—C11	179.3 (2)	C8—C9—C10—C11	0.5 (4)
C14—O4—C15—C16	176.3 (3)	C9—C10—C11—C12	−1.0 (4)
C15—O4—C14—O3	−0.3 (4)	C9—C10—C11—C14	178.3 (3)
S1—N1—C8—C9	−32.5 (4)	C10—C11—C14—O4	−174.3 (2)
S1—N1—C8—C13	150.0 (2)	C12—C11—C14—O3	−175.5 (3)
C1—C2—C7—C6	179.3 (3)	C12—C11—C14—O4	5.0 (4)
C1—C2—C3—C4	180.0 (3)	C10—C11—C14—O3	5.2 (5)
C3—C2—C7—C6	−1.1 (5)	C10—C11—C12—C13	0.1 (4)
C7—C2—C3—C4	0.3 (5)	C14—C11—C12—C13	−179.2 (3)
C2—C3—C4—C5	0.5 (5)	C11—C12—C13—C8	1.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.21	2.904 (3)	138
C1—H1A···O2ⁱⁱ	0.96	2.58	3.446 (5)	150
C9—H9···O2	0.93	2.38	3.025 (4)	126
C10—H10···O1ⁱⁱⁱ	0.93	2.51	3.431 (4)	172
C12—H12···N2^iv	0.93	2.62	3.426 (6)	146

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₄S
M_r	330.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	5.9360 (3), 8.1992 (4), 15.9068 (8)
β (°)	91.222 (3)
V (Å³)	774.02 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.28 × 0.23 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6266, 3077, 2306
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.106, 1.01
No. of reflections	3077
No. of parameters	210
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25
Absolute structure	Flack (1983), 1248 Freidel pairs
Absolute structure parameter	0.30 (10)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), 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
N1—H1···O3ⁱ	0.86	2.21	2.904 (3)	138
C1—H1A···O2ⁱⁱ	0.96	2.58	3.446 (5)	150
C9—H9···O2	0.93	2.38	3.025 (4)	126
C10—H10···O1ⁱⁱⁱ	0.93	2.51	3.431 (4)	172
C12—H12···N2^iv	0.93	2.62	3.426 (6)	146

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

Acknowledgements

The authors are grateful to Mr Muhammad Shafiq for his assistance and the Higher Education Commission (HEC), Pakistan, for financial support.

References

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