N-(2-Formyl­phen­yl)-4-toluene­sulfonamide: a second monoclinic polymorph

Murugavel, S.; Manikandan, N.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536812009403

organic compounds

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Volume 68| Part 4| April 2012| Pages o1009-o1010

doi:10.1107/S1600536812009403

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N-(2-Formylphenyl)-4-toluenesulfonamide: a second monoclinic polymorph

S. Murugavel,^a ^* N. Manikandan,^b D. Kannan ^c and M. Bakthadoss ^c ‡

^aDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, ^bDepartment of Physics, Bharathidasan Engineering College, Nattrampalli, Vellore 635 854, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 20 February 2012; accepted 2 March 2012; online 10 March 2012)

The title compound, C₁₄H₁₃NO₃S, (I), is a second monoclinic polymorph. The original polymorph, (II), was reported by Mahía et al. [Acta Cryst. (1999), C55, 2158–2160]. Polymorph (II) crystalllized in the space group P2₁/c (Z = 4), whereas the title polymorph (I) occurs in the space group P2₁/n (Z = 4). The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). In both polymorphs, two S(6) rings are generated by intramolecular N—H⋯O and C—H⋯O hydrogen bonds, resulting in similar molecular geometries. However, the two polymorphs differ concerning their crystal packing. In (I), molecules are linked into C(8) zigzag chains along the b axis by C—H⋯O hydrogen bonds, whereas in (II) molecules are linked by C—H⋯O hydrogen bonds, forming C(7) chains along the b axis. The title polymorph is further stabilized by intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.814 (1) Å]. These interactions are not evident in polymorph (II).

Related literature

For biological applications of sulfonamides, see: Connor (1998 ); Berredjem et al. (2000 ); Lee & Lee (2002 ); Xiao & Timberlake (2000 ). For the first monoclinic polymorph, see: Mahía et al. (1999 ). For a related structure, see: Zhang et al. (2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₃NO₃S
M_r = 275.31
Monoclinic, P 2₁ /n
a = 11.5409 (4) Å
b = 8.1345 (2) Å
c = 14.1115 (5) Å
β = 97.294 (2)°
V = 1314.06 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.940, T_max = 0.956
16047 measured reflections
4254 independent reflections
2678 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.155
S = 1.02
4254 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.94	2.655 (2)	140
C2—H2⋯O2	0.93	2.48	3.059 (2)	120
C14—H14C⋯O3ⁱ	0.96	2.52	3.439 (3)	161
C5—H5⋯Cg1ⁱⁱ	0.93	2.82	3.658 (2)	150
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812009403/im2360sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009403/im2360Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009403/im2360Isup3.cml

checkCIF report

Comment top

Sulfonamides are an important category of pharmaceutical compounds with a broad spectrum of biological activities such as herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Connor, 1998; Xiao & Timberlake, 2000; Berredjem et al., 2000; Lee & Lee, 2002). In this work we report the crystal structure of the title compound (Fig 1, Alternative name: 2–tosylaminobenzaldehyde), which is the second monoclinic polymorph reported.

The original polymorph (compound (II)) was previously reported by Mahía et al. (1999) and was shown to crystallize in the monoclinic space group P2₁/c, with a = 13.899 (7), b = 8.237 (4), c = 12.063 (6) Å, β = 105.899 (1)° and Z = 4. In the present work, the title compound crystallized in the space group P2₁/n with a = 11.5409 (4), b = 8.1345 (2), c = 14.1115 (5) Å, β = 97.294 (2)° and Z = 4. The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). The bond distances in the molecule are normal and comparable to those in the previously published polymorph and in a closely related sulfonamide derivative (Zhang et al., 2010).

In both polymorphs, the molecular packing is stabilized by intramolecular N1—H1···O1 and C2—H2···O2 hydrogen bonds, generating two S(6) rings (Bernstein et al., 1995) (Table 1). However, the two polymorphs differ concerning their crystal packing. In compound (II) molecules are linked to form C(7) chains along the b axis by intermolecular C3—H3···O3 hydrogen bonds whereas in the title compound (I), molecules are linked by intermolecular C14—H14C···O3 hydrogen bonds to form C(8) zigzag chains along the b axis (Fig. 2). The crystal packing (Fig. 3) is further stabilized by C—H···π interactions between a formylphenyl H atom and the benzene ring (C8–C13) of a neighbouring molecule, with a C5—H5···Cg1ⁱⁱ distance of 3.658 (2) Å (Table 1; Cg1 is the centroid of the C8–C13 benzene ring, Symmetry code: ii = 1 - x, 1 - y, -z). Additional stability arises from aromatic π—π interaction between the benzene rings of neighbouring molecules, with Cg2—Cg2ⁱⁱ distance of 3.814 (1) Å (Fig. 3; Cg2 is the centroid of the C1—C6 benzene ring, Symmetry code: ii = 1 - x, 1 - y, -z). The C—H···π and π—π interactions are not evident in compound (II).

Related literature top

For biological applications of sulfonamides, see: Connor (1998); Berredjem et al. (2000); Lee & Lee (2002); Xiao & Timberlake (2000). For the first monoclinic polymorph, see: Mahía et al. (1999). For a related structure, see: Zhang et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a stirred solution of (2-aminophenyl)methanol in chloroform, 1.5 equiv of pyridine and 1.5 equiv of 4-methylbenzene-1-sulfonyl chloride were added at room temperature over a period of 18 h. The resulting brown colored solution was quenched with aqueous HCl. After workup a pale brownish solid was obtained. The combined organic fractions were dried over Na₂SO₄ and partially concentrated under reduced pressure at 25°C. The product was precipitated with diethylether. Further, MnO₂ was added to a solution of 2-tosylaminobenzyl alcohol in dry 1,2-dichloroethane solvent under nitrogen atmosphere. The suspension was stirred at 80°C in reflux condition for 5 h and filtered through Celite. The filtrate was partially concentrated on a rotatory evaporator at 25°C and the product was precipitated with diethylether. Recystallization of the product from CH₂Cl₂ yielded pale yellow crystals of the title compound (Yield: 86%). Crystals of the original polymorph were prepared by evaporation of CHCl₃ from a solution of the title compound at room temperature (Mahía et al., 1999).

Structure description top

For biological applications of sulfonamides, see: Connor (1998); Berredjem et al. (2000); Lee & Lee (2002); Xiao & Timberlake (2000). For the first monoclinic polymorph, see: Mahía et al. (1999). For a related structure, see: Zhang et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of (I) showing C—H···O hydrogen bonds (blue dotted lines), with the formation of C(8) chains along the b axis. [Symmetry codes: (i) x, 1 + y, z; (iii) x, 2 + y, z].
	Fig. 3. A view of the C—H···π and π—π interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denotes centroids of the C8–C13 benzene ring and C1–C6 benzene ring, respectively. [Symmetry code: (ii) 1 - x, 1 - y, -z].

N-(2-Formylphenyl)-p–toluenesulfonamide top

Crystal data top

C₁₄H₁₃NO₃S	F(000) = 576
M_r = 275.31	D_x = 1.392 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4561 reflections
a = 11.5409 (4) Å	θ = 2.2–32.0°
b = 8.1345 (2) Å	µ = 0.25 mm⁻¹
c = 14.1115 (5) Å	T = 293 K
β = 97.294 (2)°	Block, pale yellow
V = 1314.06 (7) Å³	0.25 × 0.23 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4254 independent reflections
Radiation source: fine-focus sealed tube	2678 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.0 pixels mm^-1	θ_max = 32.0°, θ_min = 2.2°
ω scans	h = −15→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
T_min = 0.940, T_max = 0.956	l = −16→21
16047 measured reflections

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.0735P)² + 0.2545P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4254 reflections	Δρ_max = 0.30 e Å⁻³
174 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (3)

Crystal data top

C₁₄H₁₃NO₃S	V = 1314.06 (7) Å³
M_r = 275.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5409 (4) Å	µ = 0.25 mm⁻¹
b = 8.1345 (2) Å	T = 293 K
c = 14.1115 (5) Å	0.25 × 0.23 × 0.18 mm
β = 97.294 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4254 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2678 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.956	R_int = 0.029
16047 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
4254 reflections	Δρ_min = −0.40 e Å⁻³
174 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	0.52951 (5)	0.12891 (6)	0.23059 (3)	0.06087 (19)
C1	0.56496 (14)	0.25944 (19)	0.05828 (10)	0.0454 (4)
C6	0.51658 (14)	0.27675 (19)	−0.03793 (11)	0.0472 (4)
N1	0.50096 (14)	0.1677 (2)	0.11710 (10)	0.0566 (4)
H1	0.4372	0.1256	0.0892	0.068*
C5	0.57925 (17)	0.3623 (2)	−0.10019 (12)	0.0580 (4)
H5	0.5484	0.3721	−0.1641	0.070*
O1	0.33743 (12)	0.13376 (18)	−0.03182 (11)	0.0708 (4)
C8	0.49992 (15)	0.3098 (2)	0.29018 (11)	0.0497 (4)
C13	0.58899 (15)	0.4156 (2)	0.32385 (12)	0.0563 (4)
H13	0.6657	0.3916	0.3151	0.068*
C7	0.40286 (17)	0.2107 (2)	−0.07598 (13)	0.0608 (5)
H7	0.3780	0.2293	−0.1404	0.073*
C2	0.67100 (15)	0.3343 (2)	0.08926 (12)	0.0556 (4)
H2	0.7026	0.3273	0.1531	0.067*
O2	0.65042 (14)	0.0934 (2)	0.25269 (11)	0.0804 (5)
C11	0.45109 (18)	0.5950 (2)	0.38535 (13)	0.0614 (5)
C12	0.56359 (17)	0.5566 (3)	0.37043 (14)	0.0627 (5)
H12	0.6239	0.6281	0.3925	0.075*
C4	0.68487 (18)	0.4321 (3)	−0.06949 (15)	0.0640 (5)
H4	0.7262	0.4877	−0.1120	0.077*
C10	0.36292 (18)	0.4862 (3)	0.35138 (15)	0.0680 (5)
H10	0.2864	0.5098	0.3608	0.082*
O3	0.44396 (17)	0.0087 (2)	0.24676 (12)	0.0891 (5)
C3	0.72931 (17)	0.4190 (2)	0.02550 (15)	0.0612 (5)
H3	0.8004	0.4686	0.0470	0.073*
C9	0.38592 (17)	0.3451 (3)	0.30435 (14)	0.0626 (5)
H9	0.3257	0.2736	0.2821	0.075*
C14	0.4263 (3)	0.7500 (3)	0.43715 (17)	0.0867 (7)
H14A	0.4874	0.7685	0.4888	0.130*
H14B	0.3530	0.7394	0.4620	0.130*
H14C	0.4226	0.8412	0.3937	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0805 (4)	0.0561 (3)	0.0451 (2)	0.0081 (2)	0.0047 (2)	0.00904 (18)
C1	0.0500 (9)	0.0445 (8)	0.0410 (7)	0.0082 (7)	0.0029 (6)	−0.0031 (6)
C6	0.0532 (9)	0.0437 (8)	0.0427 (8)	0.0071 (7)	−0.0011 (6)	−0.0044 (6)
N1	0.0595 (9)	0.0669 (9)	0.0423 (7)	−0.0054 (7)	0.0017 (6)	0.0015 (6)
C5	0.0707 (12)	0.0595 (10)	0.0421 (8)	0.0054 (8)	0.0008 (8)	0.0025 (7)
O1	0.0607 (8)	0.0794 (10)	0.0696 (9)	−0.0118 (7)	−0.0021 (7)	−0.0111 (7)
C8	0.0514 (9)	0.0599 (9)	0.0378 (7)	0.0042 (7)	0.0054 (6)	0.0084 (7)
C13	0.0441 (9)	0.0767 (12)	0.0476 (9)	0.0044 (8)	0.0039 (7)	0.0005 (8)
C7	0.0642 (12)	0.0651 (11)	0.0489 (9)	0.0029 (9)	−0.0086 (8)	−0.0085 (8)
C2	0.0519 (10)	0.0678 (11)	0.0445 (8)	0.0046 (8)	−0.0039 (7)	−0.0020 (7)
O2	0.0930 (11)	0.0843 (10)	0.0605 (8)	0.0407 (8)	−0.0041 (7)	0.0065 (7)
C11	0.0777 (13)	0.0623 (11)	0.0476 (9)	0.0109 (9)	0.0218 (9)	0.0132 (8)
C12	0.0633 (11)	0.0707 (12)	0.0548 (10)	−0.0064 (9)	0.0098 (8)	−0.0037 (9)
C4	0.0695 (12)	0.0635 (11)	0.0608 (11)	−0.0013 (9)	0.0150 (9)	0.0072 (9)
C10	0.0535 (11)	0.0891 (15)	0.0649 (12)	0.0125 (10)	0.0210 (9)	0.0108 (10)
O3	0.1354 (14)	0.0640 (9)	0.0700 (10)	−0.0193 (9)	0.0206 (9)	0.0124 (7)
C3	0.0514 (10)	0.0642 (11)	0.0672 (12)	−0.0025 (8)	0.0043 (8)	−0.0027 (9)
C9	0.0498 (10)	0.0785 (13)	0.0606 (11)	−0.0063 (9)	0.0115 (8)	0.0067 (9)
C14	0.128 (2)	0.0684 (13)	0.0712 (14)	0.0182 (14)	0.0426 (14)	0.0085 (11)

Geometric parameters (Å, º) top

S1—O2	1.4204 (16)	C7—H7	0.9300
S1—O3	1.4285 (16)	C2—C3	1.375 (3)
S1—N1	1.6245 (14)	C2—H2	0.9300
S1—C8	1.7500 (18)	C11—C12	1.377 (3)
C1—C2	1.387 (2)	C11—C10	1.387 (3)
C1—N1	1.395 (2)	C11—C14	1.503 (3)
C1—C6	1.408 (2)	C12—H12	0.9300
C6—C5	1.393 (2)	C4—C3	1.377 (3)
C6—C7	1.456 (3)	C4—H4	0.9300
N1—H1	0.8600	C10—C9	1.369 (3)
C5—C4	1.364 (3)	C10—H10	0.9300
C5—H5	0.9300	C3—H3	0.9300
O1—C7	1.212 (2)	C9—H9	0.9300
C8—C13	1.378 (3)	C14—H14A	0.9600
C8—C9	1.386 (3)	C14—H14B	0.9600
C13—C12	1.372 (3)	C14—H14C	0.9600
C13—H13	0.9300

O2—S1—O3	120.36 (11)	C3—C2—C1	119.95 (16)
O2—S1—N1	109.05 (9)	C3—C2—H2	120.0
O3—S1—N1	103.45 (9)	C1—C2—H2	120.0
O2—S1—C8	108.16 (9)	C12—C11—C10	117.85 (19)
O3—S1—C8	108.55 (9)	C12—C11—C14	120.4 (2)
N1—S1—C8	106.44 (8)	C10—C11—C14	121.76 (19)
C2—C1—N1	124.04 (14)	C13—C12—C11	121.71 (19)
C2—C1—C6	119.08 (15)	C13—C12—H12	119.1
N1—C1—C6	116.87 (15)	C11—C12—H12	119.1
C5—C6—C1	118.94 (15)	C5—C4—C3	118.96 (18)
C5—C6—C7	117.88 (15)	C5—C4—H4	120.5
C1—C6—C7	123.17 (16)	C3—C4—H4	120.5
C1—N1—S1	129.33 (12)	C9—C10—C11	121.57 (18)
C1—N1—H1	115.3	C9—C10—H10	119.2
S1—N1—H1	115.3	C11—C10—H10	119.2
C4—C5—C6	121.47 (16)	C2—C3—C4	121.53 (18)
C4—C5—H5	119.3	C2—C3—H3	119.2
C6—C5—H5	119.3	C4—C3—H3	119.2
C13—C8—C9	120.11 (18)	C10—C9—C8	119.3 (2)
C13—C8—S1	120.54 (13)	C10—C9—H9	120.3
C9—C8—S1	119.35 (15)	C8—C9—H9	120.3
C12—C13—C8	119.45 (17)	C11—C14—H14A	109.5
C12—C13—H13	120.3	C11—C14—H14B	109.5
C8—C13—H13	120.3	H14A—C14—H14B	109.5
O1—C7—C6	126.30 (17)	C11—C14—H14C	109.5
O1—C7—H7	116.9	H14A—C14—H14C	109.5
C6—C7—H7	116.9	H14B—C14—H14C	109.5

C2—C1—C6—C5	2.9 (2)	C9—C8—C13—C12	−0.8 (3)
N1—C1—C6—C5	−177.73 (15)	S1—C8—C13—C12	−179.94 (14)
C2—C1—C6—C7	−176.46 (16)	C5—C6—C7—O1	−179.95 (18)
N1—C1—C6—C7	2.9 (2)	C1—C6—C7—O1	−0.6 (3)
C2—C1—N1—S1	1.3 (3)	N1—C1—C2—C3	178.36 (16)
C6—C1—N1—S1	−178.02 (13)	C6—C1—C2—C3	−2.3 (3)
O2—S1—N1—C1	−41.57 (18)	C8—C13—C12—C11	0.6 (3)
O3—S1—N1—C1	−170.79 (16)	C10—C11—C12—C13	−0.2 (3)
C8—S1—N1—C1	74.91 (17)	C14—C11—C12—C13	179.64 (18)
C1—C6—C5—C4	−1.3 (3)	C6—C5—C4—C3	−0.9 (3)
C7—C6—C5—C4	178.06 (17)	C12—C11—C10—C9	−0.1 (3)
O2—S1—C8—C13	18.43 (17)	C14—C11—C10—C9	−179.92 (19)
O3—S1—C8—C13	150.58 (15)	C1—C2—C3—C4	0.1 (3)
N1—S1—C8—C13	−98.64 (15)	C5—C4—C3—C2	1.5 (3)
O2—S1—C8—C9	−160.77 (14)	C11—C10—C9—C8	−0.1 (3)
O3—S1—C8—C9	−28.61 (16)	C13—C8—C9—C10	0.5 (3)
N1—S1—C8—C9	82.16 (15)	S1—C8—C9—C10	179.68 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.94	2.655 (2)	140
C2—H2···O2	0.93	2.48	3.059 (2)	120
C14—H14C···O3ⁱ	0.96	2.52	3.439 (3)	161
C5—H5···Cg1ⁱⁱ	0.93	2.82	3.658 (2)	150

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₃S
M_r	275.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.5409 (4), 8.1345 (2), 14.1115 (5)
β (°)	97.294 (2)
V (Å³)	1314.06 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.25 × 0.23 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.940, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	16047, 4254, 2678
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.746

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.155, 1.02
No. of reflections	4254
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.40

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.94	2.655 (2)	140.0
C2—H2···O2	0.93	2.48	3.059 (2)	120.0
C14—H14C···O3ⁱ	0.96	2.52	3.439 (3)	160.5
C5—H5···Cg1ⁱⁱ	0.93	2.82	3.658 (2)	150.0

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

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

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Volume 68| Part 4| April 2012| Pages o1009-o1010

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