4-Chloro-N-(2,3-dimethyl­phen­yl)benzamide

Rodrigues, V.Z.; Kameníček,, J.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S1600536811053256

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o202

doi:10.1107/S1600536811053256

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4-Chloro-N-(2,3-dimethylphenyl)benzamide

Vinola Z. Rodrigues,^a Jiří Kameníček,,^b B. Thimme Gowda ^a ^* and Jozef Kožíšek ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bDepartment of Inorganic Chemistry, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech Republic, and ^cInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 30 November 2011; accepted 10 December 2011; online 21 December 2011)

In the title compound, C₁₅H₁₄ClNO, the ortho- and meta-methyl substituents in the aniline ring are anti to the N—H bond. The dihedral angle between the benzoyl and aniline benzene rings is 95.0 (1)°. N—H⋯O hydrogen bonds and C—H⋯π interactions link the molecules in the crystal structure.

Related literature

For the preparation of the title compound, see: Gowda et al. (1996 , 2001 ). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ); Gowda et al. (2001); Rodrigues et al. (2011 ), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004 ), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ) and on N-chloroarylamides, see: Gowda et al. (1996).

Experimental

Crystal data

C₁₅H₁₄ClNO
M_r = 259.72
Monoclinic, P 2₁ /c
a = 8.1082 (8) Å
b = 19.5189 (17) Å
c = 9.2943 (9) Å
β = 111.957 (11)°
V = 1364.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.90 × 0.15 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.953, T_max = 0.976
22574 measured reflections
2793 independent reflections
1923 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.145
S = 1.04
2793 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C2–C7 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.18	2.904 (2)	141
C14—H14A⋯Cg1ⁱⁱ	0.96	2.94	3.653 (2)	132
C7—H7⋯Cg2ⁱ	0.93	2.76	3.612 (2)	154
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053256/bq2325sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053256/bq2325Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053256/bq2325Isup3.cml

checkCIF report

Comment top

The structural aspects of N-aryl amides are of interest due to their chemical and biological importance. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2001; Rodrigues et al., 2011), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2005) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, crystal structure of 4-chloro-N-(2,3-dimethylphenyl)benzamide (I) has been determined (Fig.1). In (I), the ortho- and meta-methyl substituents in the anilino ring are positioned anti to the N–H bond, similar to that observed in 4-methyl-N-(2,3-dimethylphenyl)benzamide (II) (Rodrigues et al., 2011).

The central amide group –NHCO– is tilted to the anilino ring with the C9—C8—N1—C1 and C13—C8—N1—C1 torsion angles of -64.2 (3)° and 117.4 (2)°, compared to the corresponding values of -63.4 (2)° and 118.1 (1)° in (II). The C3—C2—C1—N1 and C7—C2—C1—N1 torsion angles are 158.0 (2)° and -22.5 (3)°, respectively, in contrast to the corresponding angles of 156.8 (1)° and -24.4 (2)° in (II). The C3—C2—C1—O1 and C7—C2—C1—O1 torsion angles are -21.9 (3)° and 157.6 (2)°, respectively, compared to the values of -23.2 (2)° and 155.6 (1)° in (II). The planes of two benzene rings are tilted relative to each other by 95.0 (1)°.

There are two clear C—H···pi interactions in the structure, C7—H7···Cg2 (Cg2 is the centroid of C8—C13 ring) and C14—H14A···Cg1 (Cg1 is the centroid of C2—C7 ring).

The packing of molecules linked by N—H···O hydrogen bonds is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Gowda et al. (1996, 2001). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2001); Rodrigues et al. (2011), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005) and on N-chloroarylamides, see: Gowda et al. (1996).

Experimental top

The title compound was prepared according to the method described by Gowda et al. (1996, 2001). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.

Rod-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: enCIFer (Allen et al., 2004).

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. Part of the crystal structure of the title compound generated by N—H···O hydrogen bonds which are shown by dashed lines. C-H···π interactions are shown by thin dashed lines. H atoms not involved in intermolecular bonding have been omitted.

4-Chloro-N-(2,3-dimethylphenyl)benzamide top

Crystal data top

C₁₅H₁₄ClNO	F(000) = 544
M_r = 259.72	D_x = 1.265 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3994 reflections
a = 8.1082 (8) Å	θ = 3.4–26.4°
b = 19.5189 (17) Å	µ = 0.27 mm⁻¹
c = 9.2943 (9) Å	T = 293 K
β = 111.957 (11)°	Rod, colorless
V = 1364.3 (2) Å³	0.90 × 0.15 × 0.09 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2793 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1923 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
Detector resolution: 10.4340 pixels mm^-1	θ_max = 26.4°, θ_min = 3.4°
ω scans	h = −10→10
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −24→24
T_min = 0.953, T_max = 0.976	l = −11→11
22574 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0671P)² + 0.3246P] where P = (F_o² + 2F_c²)/3
2793 reflections	(Δ/σ)_max < 0.001
165 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₅H₁₄ClNO	V = 1364.3 (2) Å³
M_r = 259.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1082 (8) Å	µ = 0.27 mm⁻¹
b = 19.5189 (17) Å	T = 293 K
c = 9.2943 (9) Å	0.90 × 0.15 × 0.09 mm
β = 111.957 (11)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2793 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	1923 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.976	R_int = 0.058
22574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.04	Δρ_max = 0.40 e Å⁻³
2793 reflections	Δρ_min = −0.30 e Å⁻³
165 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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
C1	0.7781 (3)	0.70473 (10)	0.5747 (2)	0.0420 (5)
C2	0.6708 (3)	0.65266 (10)	0.6192 (2)	0.0412 (5)
C3	0.5249 (3)	0.62384 (11)	0.5034 (2)	0.0512 (6)
H3	0.4980	0.6366	0.4007	0.061*
C4	0.4194 (3)	0.57674 (12)	0.5382 (3)	0.0569 (6)
H4	0.3211	0.5579	0.4600	0.068*
C5	0.4614 (3)	0.55780 (11)	0.6907 (3)	0.0520 (6)
C6	0.6067 (3)	0.58405 (11)	0.8067 (3)	0.0527 (6)
H6	0.6348	0.5700	0.9087	0.063*
C7	0.7116 (3)	0.63166 (11)	0.7710 (2)	0.0477 (5)
H7	0.8106	0.6498	0.8496	0.057*
C8	0.9834 (3)	0.80088 (10)	0.6627 (2)	0.0409 (5)
C9	1.1274 (3)	0.78514 (11)	0.6215 (2)	0.0442 (5)
C10	1.2233 (3)	0.83941 (13)	0.5917 (3)	0.0555 (6)
C11	1.1751 (3)	0.90633 (14)	0.6085 (3)	0.0653 (7)
H11	1.2375	0.9423	0.5867	0.078*
C12	1.0378 (3)	0.92083 (12)	0.6563 (3)	0.0605 (6)
H12	1.0103	0.9660	0.6697	0.073*
C13	0.9411 (3)	0.86789 (11)	0.6842 (2)	0.0488 (5)
H13	0.8483	0.8771	0.7171	0.059*
C14	1.1822 (3)	0.71233 (12)	0.6117 (3)	0.0608 (6)
H14A	1.3083	0.7079	0.6662	0.073*
H14B	1.1521	0.7000	0.5049	0.073*
H14C	1.1214	0.6825	0.6576	0.073*
C15	1.3817 (4)	0.82577 (19)	0.5477 (3)	0.0854 (9)
H15A	1.4244	0.8683	0.5228	0.103*
H15B	1.3471	0.7959	0.4592	0.103*
H15C	1.4742	0.8045	0.6332	0.103*
N1	0.8765 (2)	0.74774 (8)	0.68807 (18)	0.0440 (4)
H1	0.8747	0.7429	0.7794	0.053*
O1	0.7749 (2)	0.70745 (8)	0.44138 (16)	0.0549 (4)
Cl1	0.32708 (12)	0.49969 (4)	0.73735 (11)	0.0947 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0504 (12)	0.0442 (11)	0.0388 (11)	0.0029 (9)	0.0251 (10)	0.0015 (8)
C2	0.0484 (12)	0.0416 (11)	0.0401 (11)	0.0007 (9)	0.0240 (9)	−0.0021 (8)
C3	0.0616 (14)	0.0523 (13)	0.0416 (12)	−0.0033 (11)	0.0214 (11)	−0.0019 (9)
C4	0.0549 (14)	0.0555 (14)	0.0572 (14)	−0.0105 (11)	0.0172 (11)	−0.0070 (11)
C5	0.0592 (14)	0.0420 (12)	0.0643 (14)	−0.0042 (10)	0.0338 (12)	0.0003 (10)
C6	0.0682 (15)	0.0497 (13)	0.0467 (12)	0.0001 (11)	0.0287 (12)	0.0061 (10)
C7	0.0559 (13)	0.0501 (13)	0.0402 (11)	−0.0053 (10)	0.0216 (10)	0.0008 (9)
C8	0.0455 (11)	0.0463 (11)	0.0326 (10)	0.0001 (9)	0.0166 (9)	0.0014 (8)
C9	0.0438 (11)	0.0568 (13)	0.0330 (10)	0.0028 (9)	0.0154 (9)	0.0018 (9)
C10	0.0445 (12)	0.0769 (17)	0.0438 (12)	−0.0080 (11)	0.0150 (10)	0.0031 (11)
C11	0.0634 (16)	0.0702 (17)	0.0576 (14)	−0.0220 (13)	0.0174 (13)	0.0082 (12)
C12	0.0665 (16)	0.0459 (13)	0.0603 (15)	−0.0044 (11)	0.0137 (13)	−0.0010 (10)
C13	0.0507 (12)	0.0474 (12)	0.0482 (12)	0.0028 (10)	0.0184 (10)	−0.0032 (9)
C14	0.0598 (14)	0.0712 (16)	0.0548 (14)	0.0188 (12)	0.0254 (12)	−0.0006 (11)
C15	0.0616 (17)	0.130 (3)	0.0768 (19)	−0.0217 (17)	0.0397 (15)	−0.0039 (17)
N1	0.0571 (11)	0.0474 (10)	0.0365 (9)	−0.0051 (8)	0.0279 (8)	−0.0030 (7)
O1	0.0729 (11)	0.0630 (10)	0.0374 (8)	−0.0119 (8)	0.0306 (8)	−0.0022 (6)
Cl1	0.1000 (6)	0.0811 (5)	0.1190 (7)	−0.0323 (4)	0.0592 (5)	0.0043 (4)

Geometric parameters (Å, º) top

C1—O1	1.231 (2)	C9—C10	1.401 (3)
C1—N1	1.350 (3)	C9—C14	1.502 (3)
C1—C2	1.493 (3)	C10—C11	1.389 (4)
C2—C7	1.385 (3)	C10—C15	1.510 (3)
C2—C3	1.386 (3)	C11—C12	1.374 (3)
C3—C4	1.374 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.379 (3)
C4—C5	1.378 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.365 (3)	C14—H14A	0.9600
C5—Cl1	1.736 (2)	C14—H14B	0.9600
C6—C7	1.381 (3)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—C13	1.386 (3)	C15—H15C	0.9600
C8—C9	1.393 (3)	N1—H1	0.8600
C8—N1	1.427 (2)

O1—C1—N1	122.86 (18)	C11—C10—C9	119.2 (2)
O1—C1—C2	120.85 (18)	C11—C10—C15	120.0 (2)
N1—C1—C2	116.28 (16)	C9—C10—C15	120.7 (2)
C7—C2—C3	118.69 (19)	C12—C11—C10	121.7 (2)
C7—C2—C1	122.75 (18)	C12—C11—H11	119.1
C3—C2—C1	118.55 (17)	C10—C11—H11	119.1
C4—C3—C2	121.0 (2)	C11—C12—C13	119.5 (2)
C4—C3—H3	119.5	C11—C12—H12	120.2
C2—C3—H3	119.5	C13—C12—H12	120.2
C3—C4—C5	119.0 (2)	C12—C13—C8	119.4 (2)
C3—C4—H4	120.5	C12—C13—H13	120.3
C5—C4—H4	120.5	C8—C13—H13	120.3
C6—C5—C4	121.3 (2)	C9—C14—H14A	109.5
C6—C5—Cl1	118.99 (17)	C9—C14—H14B	109.5
C4—C5—Cl1	119.68 (18)	H14A—C14—H14B	109.5
C5—C6—C7	119.3 (2)	C9—C14—H14C	109.5
C5—C6—H6	120.3	H14A—C14—H14C	109.5
C7—C6—H6	120.3	H14B—C14—H14C	109.5
C6—C7—C2	120.6 (2)	C10—C15—H15A	109.5
C6—C7—H7	119.7	C10—C15—H15B	109.5
C2—C7—H7	119.7	H15A—C15—H15B	109.5
C13—C8—C9	121.75 (19)	C10—C15—H15C	109.5
C13—C8—N1	117.64 (18)	H15A—C15—H15C	109.5
C9—C8—N1	120.59 (18)	H15B—C15—H15C	109.5
C8—C9—C10	118.2 (2)	C1—N1—C8	122.76 (15)
C8—C9—C14	121.53 (19)	C1—N1—H1	118.6
C10—C9—C14	120.3 (2)	C8—N1—H1	118.6

O1—C1—C2—C7	157.6 (2)	C13—C8—C9—C14	174.67 (19)
N1—C1—C2—C7	−22.5 (3)	N1—C8—C9—C14	−3.7 (3)
O1—C1—C2—C3	−21.9 (3)	C8—C9—C10—C11	1.9 (3)
N1—C1—C2—C3	157.99 (19)	C14—C9—C10—C11	−177.1 (2)
C7—C2—C3—C4	1.8 (3)	C8—C9—C10—C15	179.5 (2)
C1—C2—C3—C4	−178.6 (2)	C14—C9—C10—C15	0.6 (3)
C2—C3—C4—C5	−0.6 (3)	C9—C10—C11—C12	1.2 (3)
C3—C4—C5—C6	−1.1 (4)	C15—C10—C11—C12	−176.5 (2)
C3—C4—C5—Cl1	178.69 (18)	C10—C11—C12—C13	−2.0 (3)
C4—C5—C6—C7	1.4 (3)	C11—C12—C13—C8	−0.4 (3)
Cl1—C5—C6—C7	−178.32 (17)	C9—C8—C13—C12	3.5 (3)
C5—C6—C7—C2	−0.2 (3)	N1—C8—C13—C12	−178.07 (18)
C3—C2—C7—C6	−1.4 (3)	O1—C1—N1—C8	1.0 (3)
C1—C2—C7—C6	179.04 (19)	C2—C1—N1—C8	−178.89 (17)
C13—C8—C9—C10	−4.2 (3)	C13—C8—N1—C1	117.4 (2)
N1—C8—C9—C10	177.40 (17)	C9—C8—N1—C1	−64.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of C2–C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.18	2.904 (2)	141
C14—H14A···Cg1ⁱⁱ	0.96	2.94	3.653 (2)	132
C7—H7···Cg2ⁱ	0.93	2.76	3.612 (2)	154

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClNO
M_r	259.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1082 (8), 19.5189 (17), 9.2943 (9)
β (°)	111.957 (11)
V (Å³)	1364.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.90 × 0.15 × 0.09

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.953, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	22574, 2793, 1923
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.145, 1.04
No. of reflections	2793
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of C2–C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.18	2.904 (2)	141.2
C14—H14A···Cg1ⁱⁱ	0.96	2.94	3.653 (2)	132.4
C7—H7···Cg2ⁱ	0.93	2.76	3.612 (2)	153.5

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

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi for award of an RFSMS research fellowship. JK thanks the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency (Slovakia) (APVV-0202–10) for finacial support and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627–636. CAS Google Scholar
Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386–394. CAS Google Scholar
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106–112. CAS Google Scholar
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491–500. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rodrigues, V. Z., Herich, P., Gowda, B. T. & Kožíšek, J. (2011). Acta Cryst. E67, o2463. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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