2-[5-(2-Fluoro­phen­yl)-3-isobutyl-1H-pyrazol-1-yl]benzoic acid

Sreenivasa, S.; Manojkumar, K.E.; Suchetan, P.A.; Mohan, N.R.; Kumar, V.; Palakshamurthy, B.S.

doi:10.1107/S1600536812050702

organic compounds

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Volume 69| Part 2| February 2013| Page o176

doi:10.1107/S1600536812050702

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2-[5-(2-Fluorophenyl)-3-isobutyl-1H-pyrazol-1-yl]benzoic acid

S. Sreenivasa,^a ^* K. E. Manojkumar,^a P. A. Suchetan,^b N. R. Mohan,^a Vijith Kumar ^c and B. S. Palakshamurthy ^d

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^cSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012 India, and ^dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: drsreenivasa@yahoo.co.in

(Received 7 December 2012; accepted 13 December 2012; online 4 January 2013)

In the title compound, C₂₀H₁₉FN₂O₂, the dihedral angle between the aromatic rings is 62.1 (1)°, and those between the pyrazole ring and the fluorobenzene and benzoic acid rings are 52.1 (1) and 53.1 (1)°, respectively. In the crystal, molecules are linked into [010] C(7) chains by O—H⋯N hydrogen bonds.

Related literature

For background to pyrazole derivatives and their uses, see: Ramaiah et al. (1999 ).

Experimental

Crystal data

C₂₀H₁₉FN₂O₂
M_r = 338.37
Monoclinic, P 2₁ /c
a = 9.7732 (14) Å
b = 12.2671 (16) Å
c = 15.257 (2) Å
β = 106.836 (5)°
V = 1750.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.28 × 0.26 × 0.22 mm

Data collection

Bruker SMART X2S CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.975, T_max = 0.980
16424 measured reflections
3094 independent reflections
2517 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 0.98
3094 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.82	1.93	2.7118 (16)	159
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812050702/hb7011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812050702/hb7011Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812050702/hb7011Isup3.cml

checkCIF report

Comment top

The pyrazole nucleus is an important structure in numerous natural and synthetic compounds and in medicinal chemistry (e.g. Ramaiah et al., 1999). As part of our studies in this area, the title compound was synthesized and its crystal structure determined.

In the title compound, C₂₀H₁₉FN₂O₂, the dihedral angle between the aromatic rings is 62.1 (1)°, and those between the pyrazole ring and the aromatic ring containing fluorine atom and the pyrazole ring and the aromatic ring containing carboxylic group are 52.1 (1)° and 53.1 (1)°, respectively. In the crystal structure, the molecules are linked into C(7) chains through O—H···N H-bonds.

Related literature top

For background to pyrazole derivatives and their uses, see: Ramaiah et al. (1999).

Experimental top

1-(2-Fluorophenyl)-5-methyl-hexane-1,3-dione (0.01 mmol) and 2-hydrazinobenzoic acid (0.01 mmol) were taken in 15 ml ethanol and the mixture was heated for 12 h. The reaction was monitored by TLC. The solvent was removed by vacuum. The crude mass obtained was purified by column chromatography.

Colourless prisms were obtained by slow evaporation of the solution of the compound in a mixture of dichloromethane and methanol (9:1).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound.

2-[5-(2-Fluorophenyl)-3-isobutyl-1H-pyrazol-1-yl]benzoic acid top

Crystal data top

C₂₀H₁₉FN₂O₂	Prism
M_r = 338.37	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 514 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.7732 (14) Å	Cell parameters from 228 reflections
b = 12.2671 (16) Å	θ = 2.2–25°
c = 15.257 (2) Å	µ = 0.09 mm⁻¹
β = 106.836 (5)°	T = 293 K
V = 1750.7 (4) Å³	Prism, colourless
Z = 4	0.28 × 0.26 × 0.22 mm
F(000) = 712

Data collection top

Bruker SMART X2S CCD diffractometer	3094 independent reflections
Radiation source: fine-focus sealed tube	2517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 1.20 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −14→13
T_min = 0.975, T_max = 0.980	l = −13→18
16424 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0699P)² + 0.3164P] where P = (F_o² + 2F_c²)/3
3094 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³
0 constraints

Crystal data top

C₂₀H₁₉FN₂O₂	V = 1750.7 (4) Å³
M_r = 338.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7732 (14) Å	µ = 0.09 mm⁻¹
b = 12.2671 (16) Å	T = 293 K
c = 15.257 (2) Å	0.28 × 0.26 × 0.22 mm
β = 106.836 (5)°

Data collection top

Bruker SMART X2S CCD diffractometer	3094 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2517 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.980	R_int = 0.042
16424 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 0.98	Δρ_max = 0.23 e Å⁻³
3094 reflections	Δρ_min = −0.21 e Å⁻³
228 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
C1	0.67611 (17)	0.18408 (13)	0.80869 (11)	0.0433 (4)
C2	0.57943 (19)	0.10016 (18)	0.78124 (12)	0.0593 (5)
H2	0.4818	0.1141	0.7611	0.071*
C3	0.6306 (2)	−0.00440 (16)	0.78423 (13)	0.0650 (6)
H3	0.5671	−0.0621	0.7658	0.078*
C4	0.7749 (2)	−0.02427 (14)	0.81427 (13)	0.0610 (5)
H4	0.8088	−0.0953	0.8160	0.073*
C5	0.86956 (18)	0.06077 (13)	0.84190 (12)	0.0477 (4)
H5	0.9671	0.0463	0.8628	0.057*
C6	0.82182 (15)	0.16797 (12)	0.83906 (9)	0.0357 (3)
C7	0.92409 (15)	0.25727 (11)	0.87236 (10)	0.0340 (3)
C8	1.02695 (16)	0.26669 (12)	0.95519 (10)	0.0392 (4)
H8	1.0485	0.2159	1.0024	0.047*
C9	1.09279 (16)	0.36759 (12)	0.95454 (10)	0.0378 (4)
C10	1.21498 (18)	0.41685 (14)	1.02714 (11)	0.0511 (4)
H10A	1.1961	0.4095	1.0859	0.061*
H10B	1.2195	0.4941	1.0147	0.061*
C11	1.36062 (19)	0.36548 (15)	1.03400 (12)	0.0583 (5)
H11	1.4327	0.4099	1.0773	0.070*
C12	1.3732 (2)	0.25065 (17)	1.07315 (17)	0.0761 (6)
H12A	1.3115	0.2026	1.0295	0.114*
H12B	1.3458	0.2508	1.1287	0.114*
H12C	1.4703	0.2261	1.0859	0.114*
C13	1.3945 (3)	0.3702 (3)	0.94334 (17)	0.0942 (8)
H13A	1.3313	0.3224	0.9003	0.141*
H13B	1.4916	0.3478	0.9519	0.141*
H13C	1.3821	0.4435	0.9203	0.141*
C14	0.85515 (14)	0.37883 (11)	0.73233 (9)	0.0314 (3)
C15	0.78672 (16)	0.47868 (12)	0.71577 (10)	0.0393 (4)
H15	0.7900	0.5255	0.7643	0.047*
C16	0.71348 (18)	0.50905 (13)	0.62735 (11)	0.0461 (4)
H16	0.6707	0.5774	0.6164	0.055*
C17	0.70354 (17)	0.43865 (14)	0.55532 (11)	0.0484 (4)
H17	0.6529	0.4588	0.4960	0.058*
C18	0.76933 (17)	0.33819 (13)	0.57190 (10)	0.0426 (4)
H18	0.7602	0.2898	0.5236	0.051*
C19	0.84933 (15)	0.30803 (11)	0.65991 (10)	0.0332 (3)
C20	0.93555 (17)	0.20534 (11)	0.67171 (10)	0.0372 (4)
N1	0.93084 (12)	0.35052 (9)	0.82486 (8)	0.0327 (3)
N2	1.03412 (13)	0.41900 (9)	0.87541 (8)	0.0376 (3)
O1	0.85946 (13)	0.12237 (8)	0.62925 (8)	0.0525 (3)
H1	0.9097	0.0676	0.6370	0.079*
O2	1.06073 (13)	0.20202 (9)	0.71308 (9)	0.0558 (3)
F1	0.62576 (11)	0.28686 (9)	0.80786 (9)	0.0691 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0448 (9)	0.0438 (9)	0.0405 (8)	−0.0036 (7)	0.0111 (7)	0.0071 (7)
C2	0.0467 (9)	0.0770 (14)	0.0486 (10)	−0.0214 (9)	0.0049 (8)	0.0101 (9)
C3	0.0784 (14)	0.0570 (12)	0.0561 (11)	−0.0366 (11)	0.0141 (10)	−0.0011 (9)
C4	0.0837 (14)	0.0359 (10)	0.0670 (12)	−0.0172 (9)	0.0278 (10)	−0.0013 (8)
C5	0.0543 (10)	0.0357 (9)	0.0553 (10)	−0.0059 (7)	0.0194 (8)	0.0044 (7)
C6	0.0424 (8)	0.0345 (8)	0.0312 (7)	−0.0066 (6)	0.0123 (6)	0.0035 (6)
C7	0.0395 (7)	0.0287 (7)	0.0352 (8)	−0.0021 (6)	0.0131 (6)	0.0026 (6)
C8	0.0459 (8)	0.0357 (8)	0.0341 (8)	−0.0034 (7)	0.0084 (6)	0.0070 (6)
C9	0.0454 (8)	0.0327 (8)	0.0326 (7)	−0.0025 (6)	0.0071 (6)	−0.0008 (6)
C10	0.0680 (11)	0.0402 (9)	0.0363 (8)	−0.0133 (8)	0.0013 (8)	−0.0011 (7)
C11	0.0505 (10)	0.0629 (12)	0.0505 (10)	−0.0212 (9)	−0.0026 (8)	0.0073 (9)
C12	0.0611 (12)	0.0631 (13)	0.0900 (16)	−0.0011 (10)	−0.0006 (11)	0.0129 (11)
C13	0.0682 (14)	0.141 (2)	0.0767 (15)	−0.0206 (15)	0.0256 (12)	0.0082 (15)
C14	0.0346 (7)	0.0262 (7)	0.0332 (7)	−0.0011 (6)	0.0095 (6)	0.0012 (6)
C15	0.0470 (8)	0.0290 (8)	0.0410 (8)	0.0044 (6)	0.0114 (7)	−0.0041 (6)
C16	0.0530 (9)	0.0337 (8)	0.0495 (9)	0.0118 (7)	0.0116 (7)	0.0075 (7)
C17	0.0515 (9)	0.0511 (10)	0.0376 (8)	0.0099 (8)	0.0048 (7)	0.0091 (7)
C18	0.0515 (9)	0.0414 (9)	0.0331 (8)	0.0039 (7)	0.0092 (7)	−0.0032 (7)
C19	0.0376 (7)	0.0275 (7)	0.0352 (7)	−0.0005 (6)	0.0117 (6)	−0.0016 (6)
C20	0.0500 (9)	0.0292 (8)	0.0336 (7)	0.0022 (7)	0.0140 (7)	−0.0009 (6)
N1	0.0405 (6)	0.0240 (6)	0.0314 (6)	−0.0026 (5)	0.0070 (5)	−0.0009 (5)
N2	0.0484 (7)	0.0258 (6)	0.0349 (7)	−0.0045 (5)	0.0062 (5)	−0.0029 (5)
O1	0.0647 (7)	0.0282 (6)	0.0586 (7)	0.0048 (5)	0.0083 (6)	−0.0092 (5)
O2	0.0485 (7)	0.0389 (7)	0.0751 (9)	0.0092 (5)	0.0103 (6)	−0.0032 (6)
F1	0.0516 (6)	0.0598 (7)	0.0958 (9)	0.0099 (5)	0.0212 (6)	0.0115 (6)

Geometric parameters (Å, º) top

C1—F1	1.3522 (19)	C11—H11	0.9800
C1—C6	1.378 (2)	C12—H12A	0.9600
C1—C2	1.378 (2)	C12—H12B	0.9600
C2—C3	1.373 (3)	C12—H12C	0.9600
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.373 (3)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.377 (2)	C14—C15	1.3832 (19)
C4—H4	0.9300	C14—C19	1.394 (2)
C5—C6	1.392 (2)	C14—N1	1.4338 (17)
C5—H5	0.9300	C15—C16	1.383 (2)
C6—C7	1.471 (2)	C15—H15	0.9300
C7—N1	1.3659 (18)	C16—C17	1.379 (2)
C7—C8	1.373 (2)	C16—H16	0.9300
C8—C9	1.396 (2)	C17—C18	1.379 (2)
C8—H8	0.9300	C17—H17	0.9300
C9—N2	1.3352 (18)	C18—C19	1.394 (2)
C9—C10	1.501 (2)	C18—H18	0.9300
C10—C11	1.532 (3)	C19—C20	1.497 (2)
C10—H10A	0.9700	C20—O2	1.2039 (19)
C10—H10B	0.9700	C20—O1	1.3151 (18)
C11—C13	1.514 (3)	N1—N2	1.3669 (16)
C11—C12	1.521 (3)	O1—H1	0.8200

F1—C1—C6	118.34 (14)	C11—C12—H12A	109.5
F1—C1—C2	118.56 (15)	C11—C12—H12B	109.5
C6—C1—C2	123.09 (16)	H12A—C12—H12B	109.5
C3—C2—C1	118.49 (17)	C11—C12—H12C	109.5
C3—C2—H2	120.8	H12A—C12—H12C	109.5
C1—C2—H2	120.8	H12B—C12—H12C	109.5
C2—C3—C4	120.41 (16)	C11—C13—H13A	109.5
C2—C3—H3	119.8	C11—C13—H13B	109.5
C4—C3—H3	119.8	H13A—C13—H13B	109.5
C3—C4—C5	120.13 (18)	C11—C13—H13C	109.5
C3—C4—H4	119.9	H13A—C13—H13C	109.5
C5—C4—H4	119.9	H13B—C13—H13C	109.5
C4—C5—C6	121.12 (17)	C15—C14—C19	120.03 (13)
C4—C5—H5	119.4	C15—C14—N1	118.60 (12)
C6—C5—H5	119.4	C19—C14—N1	121.37 (12)
C1—C6—C5	116.77 (14)	C16—C15—C14	120.21 (14)
C1—C6—C7	122.82 (14)	C16—C15—H15	119.9
C5—C6—C7	120.32 (14)	C14—C15—H15	119.9
N1—C7—C8	106.43 (12)	C17—C16—C15	120.39 (14)
N1—C7—C6	124.95 (12)	C17—C16—H16	119.8
C8—C7—C6	128.60 (13)	C15—C16—H16	119.8
C7—C8—C9	106.51 (13)	C16—C17—C18	119.48 (14)
C7—C8—H8	126.7	C16—C17—H17	120.3
C9—C8—H8	126.7	C18—C17—H17	120.3
N2—C9—C8	110.30 (12)	C17—C18—C19	121.03 (14)
N2—C9—C10	121.24 (13)	C17—C18—H18	119.5
C8—C9—C10	128.43 (13)	C19—C18—H18	119.5
C9—C10—C11	114.19 (15)	C14—C19—C18	118.75 (13)
C9—C10—H10A	108.7	C14—C19—C20	122.46 (13)
C11—C10—H10A	108.7	C18—C19—C20	118.58 (13)
C9—C10—H10B	108.7	O2—C20—O1	125.16 (13)
C11—C10—H10B	108.7	O2—C20—C19	122.86 (13)
H10A—C10—H10B	107.6	O1—C20—C19	111.94 (13)
C13—C11—C12	112.3 (2)	C7—N1—N2	110.89 (11)
C13—C11—C10	111.49 (16)	C7—N1—C14	129.41 (11)
C12—C11—C10	112.06 (16)	N2—N1—C14	119.52 (11)
C13—C11—H11	106.8	C9—N2—N1	105.87 (11)
C12—C11—H11	106.8	C20—O1—H1	109.5
C10—C11—H11	106.8

F1—C1—C2—C3	−178.45 (15)	C14—C15—C16—C17	2.4 (2)
C6—C1—C2—C3	0.0 (3)	C15—C16—C17—C18	−1.1 (3)
C1—C2—C3—C4	0.2 (3)	C16—C17—C18—C19	−2.0 (3)
C2—C3—C4—C5	0.2 (3)	C15—C14—C19—C18	−2.4 (2)
C3—C4—C5—C6	−0.8 (3)	N1—C14—C19—C18	177.45 (13)
F1—C1—C6—C5	177.89 (14)	C15—C14—C19—C20	172.29 (13)
C2—C1—C6—C5	−0.5 (2)	N1—C14—C19—C20	−7.9 (2)
F1—C1—C6—C7	1.4 (2)	C17—C18—C19—C14	3.7 (2)
C2—C1—C6—C7	−177.03 (15)	C17—C18—C19—C20	−171.20 (15)
C4—C5—C6—C1	0.9 (2)	C14—C19—C20—O2	−46.5 (2)
C4—C5—C6—C7	177.51 (15)	C18—C19—C20—O2	128.16 (17)
C1—C6—C7—N1	−54.0 (2)	C14—C19—C20—O1	135.65 (15)
C5—C6—C7—N1	129.63 (16)	C18—C19—C20—O1	−49.67 (19)
C1—C6—C7—C8	124.18 (18)	C8—C7—N1—N2	−0.46 (16)
C5—C6—C7—C8	−52.2 (2)	C6—C7—N1—N2	178.04 (13)
N1—C7—C8—C9	0.22 (17)	C8—C7—N1—C14	174.51 (14)
C6—C7—C8—C9	−178.22 (14)	C6—C7—N1—C14	−7.0 (2)
C7—C8—C9—N2	0.10 (18)	C15—C14—N1—C7	130.38 (16)
C7—C8—C9—C10	−178.06 (16)	C19—C14—N1—C7	−49.4 (2)
N2—C9—C10—C11	−104.15 (18)	C15—C14—N1—N2	−55.02 (18)
C8—C9—C10—C11	73.8 (2)	C19—C14—N1—N2	125.15 (14)
C9—C10—C11—C13	56.3 (2)	C8—C9—N2—N1	−0.37 (17)
C9—C10—C11—C12	−70.6 (2)	C10—C9—N2—N1	177.94 (14)
C19—C14—C15—C16	−0.6 (2)	C7—N1—N2—C9	0.52 (16)
N1—C14—C15—C16	179.57 (14)	C14—N1—N2—C9	−175.02 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.82	1.93	2.7118 (16)	159

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉FN₂O₂
M_r	338.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.7732 (14), 12.2671 (16), 15.257 (2)
β (°)	106.836 (5)
V (Å³)	1750.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.26 × 0.22

Data collection
Diffractometer	Bruker SMART X2S CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.975, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	16424, 3094, 2517
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 0.98
No. of reflections	3094
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.82	1.93	2.7118 (16)	159

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

Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, for his constant encouragement and Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions. BSP thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his guidance.

References

Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ramaiah, K., Grossert, J. S., Hooper, D. L., Dubey, P. K. & Ramanatham, J. (1999). J. Indian Chem. Soc. 76, 140–144. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar