N-(3-Meth­oxy­benzo­yl)-2-methyl­benzene­sulfonamide

Sreenivasa, S.; Darshan, D.; Prakash Shet, M.; Mohan, N.R.; Kumar, V.; Suchetan, P.A.

doi:10.1107/S1600536813018539

organic compounds

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Volume 69| Part 8| August 2013| Page o1232

doi:10.1107/S1600536813018539

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N-(3-Methoxybenzoyl)-2-methylbenzenesulfonamide

S. Sreenivasa,^a D Darshan,^b M. Prakash Shet,^c N. R. Mohan,^a Vijith Kumar ^d and P. A. Suchetan ^c ^*

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bUniversity College of Science, Tumkur University, Tumkur, India, ^cDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and ^dSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India
^*Correspondence e-mail: pasuchetan@yahoo.co.in

(Received 29 June 2013; accepted 4 July 2013; online 10 July 2013)

In the title compound, C₁₅H₁₅NO₄S, the dihedral angle between the methyl- and methoxy-substituted benzene rings is 88.99 (12)°. An intramolecular C—H⋯O hydrogen bond occurs. In the crystal, adjacent molecules form inversion-related dimers through strong N—H⋯O hydrogen bonds, generating R₂²(8) loops. The dimers are further connected through C—H⋯O interactions that form C(8) chains parallel to (001). Molecules are also connected through other C—H⋯O hydrogen bonds along the b axis, forming additional C(8) chains. Two aromatic π–π stacking interactions [centroid–centroid separations = 3.6150 (1) and 3.6837 (1) Å] generate a three-dimensional architecture.

Related literature

For similar structures, see: Gowda et al. (2010 ); Suchetan et al. (2010 , 2011 ).

Experimental

Crystal data

C₁₅H₁₅NO₄S
M_r = 305.34
Monoclinic, C 2/c
a = 26.713 (5) Å
b = 7.3717 (4) Å
c = 19.636 (3) Å
β = 131.21 (3)°
V = 2908.7 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.33 × 0.27 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
5294 measured reflections
2558 independent reflections
1970 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.118
S = 1.04
2558 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O2ⁱ	0.80 (3)	2.15 (4)	2.929 (4)	166
C3—H3⋯O3ⁱⁱ	0.93	2.60	3.463 (3)	155
C10—H10⋯O2ⁱ	0.93	2.60	3.404 (3)	145
C15—H15B⋯O3ⁱⁱⁱ	0.96	2.36	3.323 (3)	178
C6—H6⋯O1	0.93	2.46	2.861 (4)	106
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[x, -y+2, z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813018539/sj5340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018539/sj5340Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018539/sj5340Isup3.cml

checkCIF report

Comment top

As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Suchetan et al., 2010, 2011), we report herein the crystal structure of the title compound (I).

In the title compound, C₁₅H₁₅NO₄S, the dihedral angle between the benzene rings is 88.99°. In the molecule, the conformation between the N-H bond and the ortho-methyl group in the sulfonyl benzene ring is syn. This is similar to what is observed in N-(benzoyl)-2-methylbenzenesulfonamide (II, Suchetan et al., 2010), N-(3-chlorobenzoyl)- 2-methylbenzenesulfonamide (III, Suchetan et al., 2011) and N-(3-methylbenzoyl)-2-methylbenzenesulfonamide (IV, Gowda et al., 2010). Similarly, the conformation between the N-H bond and the meta-methoxy group in the benzoyl ring is syn, also similar to the conformation in III (Suchetan et al., 2011) and IV (Gowda et al., 2010).

Adjacent molecules form inversion related dimers through strong N1–HN1···O2 hydrogen bonds, Table 1, generating R²₂(8) loops. The dimers are further connected through intermolecular C10—H10···O2 interactions that form C(8) chains parallel to (001). Molecules are also connected through other intermolecular C15—H15B···O3 hydrogen bonds along the b axis forming additional C(8) chains. Two aromatic π–π stacking interactions (centroid- centroid separations 3.6150 (1) Å and 3.6837 (1) Å) are also observed.

Related literature top

For similar structures, see: Gowda et al. (2010); Suchetan et al. (2010, 2011).

Experimental top

The title compound was prepared by refluxing a mixture of 3-methoxybenzoic acid, 2-methylbenzenesulfonamide and phosphorus oxychloride, POCl₃, for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point (423 K).

Colorless prisms of (I) were obtained from a slow evaporation of its ethanolic solution at room temperature.

Computing details top

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

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines. Hydrogen atoms bound to carbon are omitted for clarity.
	Fig. 3. Display of C—H···O interactions among molecules along b axis forming C(8) chains.
	Fig. 4. Stacking of molecules through Cg···Cg interactions. Cg1 and Cg2 are the centroids of the carbonyl and sulfonyl bounded benzene rings respectively.

N-(3-Methoxybenzoyl)-2-methylbenzenesulfonamide top

Crystal data top

C₁₅H₁₅NO₄S	Prism
M_r = 305.34	D_x = 1.394 Mg m⁻³
Monoclinic, C2/c	Melting point: 423 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 26.713 (5) Å	Cell parameters from 1232 reflections
b = 7.3717 (4) Å	θ = 2.8–25.0°
c = 19.636 (3) Å	µ = 0.24 mm⁻¹
β = 131.21 (3)°	T = 293 K
V = 2908.7 (7) Å³	Prism, colourless
Z = 8	0.33 × 0.27 × 0.22 mm
F(000) = 1280

Data collection top

Bruker APEXII CCD area-detector diffractometer	1970 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.0°, θ_min = 2.8°
ϕ and ω scans	h = −31→31
5294 measured reflections	k = −8→8
2558 independent reflections	l = −14→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0544P)² + 0.0171P] where P = (F_o² + 2F_c²)/3
2558 reflections	(Δ/σ)_max = 0.001
196 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³
0 constraints

Crystal data top

C₁₅H₁₅NO₄S	V = 2908.7 (7) Å³
M_r = 305.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.713 (5) Å	µ = 0.24 mm⁻¹
b = 7.3717 (4) Å	T = 293 K
c = 19.636 (3) Å	0.33 × 0.27 × 0.22 mm
β = 131.21 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1970 reflections with I > 2σ(I)
5294 measured reflections	R_int = 0.027
2558 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.19 e Å⁻³
2558 reflections	Δρ_min = −0.35 e Å⁻³
196 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
HN1	0.0737 (12)	0.796 (3)	0.2976 (17)	0.055 (8)*
C1	0.05769 (11)	0.6312 (3)	0.13024 (14)	0.0444 (5)
C9	0.18751 (12)	0.9525 (3)	0.40254 (15)	0.0425 (5)
C10	0.16739 (12)	0.9650 (3)	0.45194 (16)	0.0479 (6)
H10	0.1231	0.9451	0.4237	0.057*
C8	0.14165 (12)	0.9088 (3)	0.30428 (16)	0.0467 (6)
C2	0.06638 (11)	0.4482 (3)	0.15570 (16)	0.0488 (6)
C6	0.07526 (12)	0.6977 (3)	0.08233 (16)	0.0546 (6)
H6	0.0689	0.8195	0.0662	0.066*
C14	0.25399 (13)	0.9826 (3)	0.44521 (17)	0.0529 (6)
H14	0.2678	0.9748	0.4125	0.063*
C11	0.21314 (12)	1.0071 (3)	0.54308 (17)	0.0496 (6)
C13	0.29856 (13)	1.0235 (3)	0.53520 (18)	0.0602 (7)
H13	0.3429	1.0430	0.5635	0.072*
C12	0.27921 (12)	1.0365 (3)	0.58542 (17)	0.0529 (6)
H12	0.3102	1.0646	0.6468	0.063*
C5	0.10253 (13)	0.5803 (4)	0.05870 (18)	0.0653 (7)
H5	0.1146	0.6233	0.0267	0.078*
C4	0.11146 (14)	0.4011 (4)	0.08281 (18)	0.0666 (8)
H4	0.1296	0.3227	0.0670	0.080*
C3	0.09384 (13)	0.3358 (3)	0.13017 (18)	0.0601 (7)
H3	0.1004	0.2136	0.1457	0.072*
C7	0.04728 (14)	0.3666 (3)	0.20628 (19)	0.0651 (7)
H7A	0.0607	0.4466	0.2543	0.098*
H7B	0.0691	0.2516	0.2312	0.098*
H7C	−0.0001	0.3496	0.1655	0.098*
C15	0.23539 (16)	1.0486 (5)	0.68140 (19)	0.0927 (11)
H15A	0.2674	0.9521	0.7117	0.139*
H15B	0.2121	1.0546	0.7032	0.139*
H15C	0.2578	1.1616	0.6934	0.139*
O1	0.00755 (9)	0.9515 (2)	0.10733 (11)	0.0614 (5)
O2	−0.02956 (7)	0.7037 (2)	0.14851 (11)	0.0527 (4)
O3	0.15524 (9)	0.9414 (2)	0.25752 (12)	0.0646 (5)
O4	0.18890 (10)	1.0151 (3)	0.58597 (13)	0.0771 (6)
S1	0.02251 (3)	0.78797 (8)	0.15606 (4)	0.0461 (2)
N1	0.08109 (10)	0.8300 (3)	0.26647 (13)	0.0456 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0325 (12)	0.0577 (14)	0.0369 (12)	−0.0007 (11)	0.0202 (11)	−0.0079 (10)
C9	0.0428 (13)	0.0396 (11)	0.0460 (14)	−0.0036 (10)	0.0296 (12)	−0.0046 (10)
C10	0.0408 (14)	0.0560 (13)	0.0514 (15)	−0.0117 (11)	0.0323 (13)	−0.0128 (11)
C8	0.0477 (15)	0.0498 (13)	0.0500 (15)	−0.0079 (11)	0.0354 (14)	−0.0059 (11)
C2	0.0370 (13)	0.0540 (13)	0.0470 (14)	−0.0035 (11)	0.0240 (13)	−0.0114 (11)
C6	0.0477 (15)	0.0703 (16)	0.0468 (15)	0.0002 (12)	0.0315 (14)	−0.0041 (12)
C14	0.0455 (15)	0.0674 (15)	0.0538 (16)	−0.0046 (12)	0.0361 (14)	−0.0031 (12)
C11	0.0479 (15)	0.0570 (13)	0.0509 (15)	−0.0084 (12)	0.0355 (14)	−0.0110 (11)
C13	0.0386 (14)	0.0809 (17)	0.0573 (17)	−0.0073 (13)	0.0299 (14)	−0.0053 (13)
C12	0.0424 (15)	0.0643 (15)	0.0435 (15)	−0.0053 (12)	0.0247 (13)	−0.0060 (11)
C5	0.0528 (17)	0.100 (2)	0.0516 (16)	−0.0027 (16)	0.0381 (15)	−0.0121 (15)
C4	0.0513 (17)	0.087 (2)	0.0610 (18)	0.0025 (15)	0.0369 (16)	−0.0217 (15)
C3	0.0491 (16)	0.0606 (15)	0.0614 (17)	0.0022 (13)	0.0324 (15)	−0.0135 (13)
C7	0.0658 (19)	0.0565 (15)	0.075 (2)	−0.0007 (13)	0.0473 (18)	0.0007 (13)
C15	0.071 (2)	0.164 (3)	0.0525 (19)	−0.016 (2)	0.0442 (19)	−0.0258 (19)
O1	0.0668 (12)	0.0571 (9)	0.0569 (12)	0.0121 (9)	0.0393 (11)	0.0084 (8)
O2	0.0360 (9)	0.0696 (10)	0.0542 (10)	−0.0035 (8)	0.0305 (9)	−0.0118 (8)
O3	0.0606 (12)	0.0922 (13)	0.0561 (12)	−0.0179 (10)	0.0449 (11)	−0.0102 (9)
O4	0.0531 (12)	0.1345 (16)	0.0517 (12)	−0.0218 (11)	0.0380 (11)	−0.0281 (11)
S1	0.0400 (4)	0.0541 (4)	0.0427 (4)	0.0021 (3)	0.0267 (3)	−0.0040 (3)
N1	0.0450 (12)	0.0577 (12)	0.0394 (12)	−0.0091 (9)	0.0301 (11)	−0.0074 (9)

Geometric parameters (Å, º) top

C1—C6	1.388 (3)	C13—H13	0.9300
C1—C2	1.404 (3)	C12—H12	0.9300
C1—S1	1.762 (2)	C5—C4	1.370 (4)
C9—C10	1.388 (3)	C5—H5	0.9300
C9—C14	1.394 (3)	C4—C3	1.376 (4)
C9—C8	1.487 (3)	C4—H4	0.9300
C10—C11	1.382 (3)	C3—H3	0.9300
C10—H10	0.9300	C7—H7A	0.9600
C8—O3	1.213 (3)	C7—H7B	0.9600
C8—N1	1.387 (3)	C7—H7C	0.9600
C2—C3	1.400 (3)	C15—O4	1.431 (3)
C2—C7	1.509 (3)	C15—H15A	0.9600
C6—C5	1.393 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C14—C13	1.363 (3)	O1—S1	1.4232 (16)
C14—H14	0.9300	O2—S1	1.4391 (16)
C11—O4	1.360 (3)	S1—N1	1.666 (2)
C11—C12	1.385 (3)	N1—HN1	0.79 (2)
C13—C12	1.386 (3)

C6—C1—C2	122.0 (2)	C4—C5—H5	120.2
C6—C1—S1	116.49 (18)	C6—C5—H5	120.2
C2—C1—S1	121.48 (17)	C5—C4—C3	120.7 (2)
C10—C9—C14	119.7 (2)	C5—C4—H4	119.6
C10—C9—C8	123.6 (2)	C3—C4—H4	119.6
C14—C9—C8	116.6 (2)	C4—C3—C2	121.9 (2)
C11—C10—C9	120.0 (2)	C4—C3—H3	119.1
C11—C10—H10	120.0	C2—C3—H3	119.1
C9—C10—H10	120.0	C2—C7—H7A	109.5
O3—C8—N1	120.2 (2)	C2—C7—H7B	109.5
O3—C8—C9	122.5 (2)	H7A—C7—H7B	109.5
N1—C8—C9	117.3 (2)	C2—C7—H7C	109.5
C3—C2—C1	116.3 (2)	H7A—C7—H7C	109.5
C3—C2—C7	119.0 (2)	H7B—C7—H7C	109.5
C1—C2—C7	124.7 (2)	O4—C15—H15A	109.5
C1—C6—C5	119.4 (2)	O4—C15—H15B	109.5
C1—C6—H6	120.3	H15A—C15—H15B	109.5
C5—C6—H6	120.3	O4—C15—H15C	109.5
C13—C14—C9	119.5 (2)	H15A—C15—H15C	109.5
C13—C14—H14	120.2	H15B—C15—H15C	109.5
C9—C14—H14	120.2	C11—O4—C15	117.5 (2)
O4—C11—C10	115.8 (2)	O1—S1—O2	118.18 (11)
O4—C11—C12	124.0 (2)	O1—S1—N1	108.93 (10)
C10—C11—C12	120.2 (2)	O2—S1—N1	103.29 (10)
C14—C13—C12	121.4 (2)	O1—S1—C1	109.21 (11)
C14—C13—H13	119.3	O2—S1—C1	110.47 (10)
C12—C13—H13	119.3	N1—S1—C1	105.95 (11)
C11—C12—C13	119.1 (2)	C8—N1—S1	122.61 (17)
C11—C12—H12	120.4	C8—N1—HN1	120.7 (19)
C13—C12—H12	120.4	S1—N1—HN1	116.5 (19)
C4—C5—C6	119.6 (2)

C14—C9—C10—C11	0.0 (3)	C5—C4—C3—C2	−0.1 (4)
C8—C9—C10—C11	−179.7 (2)	C1—C2—C3—C4	0.1 (4)
C10—C9—C8—O3	161.3 (2)	C7—C2—C3—C4	179.1 (2)
C14—C9—C8—O3	−18.4 (3)	C10—C11—O4—C15	176.7 (2)
C10—C9—C8—N1	−17.9 (3)	C12—C11—O4—C15	−2.7 (4)
C14—C9—C8—N1	162.4 (2)	O2—O2—S1—O1	0.00 (5)
C6—C1—C2—C3	0.0 (3)	O2—O2—S1—N1	0.00 (6)
S1—C1—C2—C3	178.99 (18)	O2—O2—S1—C1	0.00 (4)
C6—C1—C2—C7	−178.9 (2)	C6—C1—S1—O1	10.5 (2)
S1—C1—C2—C7	0.1 (3)	C2—C1—S1—O1	−168.48 (18)
C2—C1—C6—C5	−0.2 (4)	C6—C1—S1—O2	142.13 (18)
S1—C1—C6—C5	−179.17 (18)	C2—C1—S1—O2	−36.9 (2)
C10—C9—C14—C13	0.2 (3)	C6—C1—S1—O2	142.13 (18)
C8—C9—C14—C13	179.9 (2)	C2—C1—S1—O2	−36.9 (2)
C9—C10—C11—O4	−179.6 (2)	C6—C1—S1—N1	−106.65 (19)
C9—C10—C11—C12	−0.1 (3)	C2—C1—S1—N1	74.3 (2)
C9—C14—C13—C12	−0.2 (4)	O3—C8—N1—S1	−3.9 (3)
O4—C11—C12—C13	179.5 (2)	C9—C8—N1—S1	175.28 (15)
C10—C11—C12—C13	0.1 (4)	O1—S1—N1—C8	−54.9 (2)
C14—C13—C12—C11	0.1 (4)	O2—S1—N1—C8	178.66 (18)
C1—C6—C5—C4	0.2 (4)	O2—S1—N1—C8	178.66 (18)
C6—C5—C4—C3	0.0 (4)	C1—S1—N1—C8	62.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O2ⁱ	0.80 (3)	2.15 (4)	2.929 (4)	166
C3—H3···O3ⁱⁱ	0.93	2.60	3.463 (3)	155
C10—H10···O2ⁱ	0.93	2.60	3.404 (3)	145
C15—H15B···O3ⁱⁱⁱ	0.96	2.36	3.323 (3)	178
C6—H6···O1	0.93	2.46	2.861 (4)	106

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₄S
M_r	305.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	26.713 (5), 7.3717 (4), 19.636 (3)
β (°)	131.21 (3)
V (Å³)	2908.7 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.33 × 0.27 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5294, 2558, 1970
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.118, 1.04
No. of reflections	2558
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.35

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O2ⁱ	0.80 (3)	2.15 (4)	2.929 (4)	166
C3—H3···O3ⁱⁱ	0.93	2.60	3.463 (3)	154.7
C10—H10···O2ⁱ	0.93	2.60	3.404 (3)	145.3
C15—H15B···O3ⁱⁱⁱ	0.96	2.36	3.323 (3)	178.0
C6—H6···O1	0.93	2.46	2.861 (4)	106

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

Acknowledgements

The authors thank Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions. PAS and MPS thank the University Grants Commission (UGC), India, for financial support under its Minor Research Project scheme.

References

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o433. Web of Science CSD CrossRef IUCr Journals Google Scholar
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