4-Methyl-5-phenyl-1H-pyrazol-3-ol

Shahani, T.; Fun, H.-K.; Ragavan, R.V.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S1600536810022828

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1697-o1698

doi:10.1107/S1600536810022828

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4-Methyl-5-phenyl-1H-pyrazol-3-ol

Tara Shahani,^a Hoong-Kun Fun,^a ^*‡ R. Venkat Ragavan,^b V. Vijayakumar ^b and S. Sarveswari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 8 June 2010; accepted 14 June 2010; online 18 June 2010)

The title compound, C₁₀H₁₀N₂O, crystallizes with two independent molecules in the asymmetric unit, having closely comparable geometries. The dihedral angles between the 1H-pyrazole and benzene rings in the two molecules are 39.57 (14) and 41.95 (13)°. The two molecules are each connected to neighbouring molecules by pairs of intermolecular O—H⋯N hydrogen bonds, forming dimers with R₂²(8) ring motifs. These dimers are further linked into R₄⁴(10) ring motifs by intermolecular N—H⋯O hydrogen bonds, forming chains along [101]. The crystal structure is further stabilized by a C—H⋯π interaction.

Related literature

For the biological activity of 4-methyl-3-phenyl-1H-pyrazol-5-ol, see: Brogden (1986 ); Gursoy et al. (2000 ); Ragavan et al. (2009 , 2010 ); Watanabe et al. (1984 ); Kawai et al. (1997 ); Wu et al. (2002 ). For related structures, see: Shahani et al. (2009 , 2010a ,b ,c ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₀H₁₀N₂O
M_r = 174.20
Monoclinic, C 2/c
a = 26.4082 (19) Å
b = 11.0972 (8) Å
c = 14.1245 (10) Å
β = 118.996 (1)°
V = 3620.4 (4) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.14 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.970, T_max = 0.993
19166 measured reflections
5255 independent reflections
2907 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.204
S = 1.13
5255 reflections
243 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1B–C6B benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯N2Aⁱ	0.83	1.85	2.673 (2)	171
O1B—H1OB⋯N2Bⁱⁱ	0.83	1.84	2.670 (2)	177
N1B—H1NB⋯O1Aⁱⁱⁱ	1.00 (3)	1.85 (3)	2.836 (3)	171 (3)
N1A—H1NA⋯O1B^iv	0.97 (3)	1.88 (3)	2.844 (2)	173 (2)
C10A—H10C⋯Cg1^v	0.96	2.77	3.575 (3)	142
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]$ ; (ii) $[-x, y, -z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x, -y+2, -z; (v) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022828/is2561sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022828/is2561Isup2.hkl

checkCIF report

Comment top

Pyrazolone derivatives have a broad spectrum of biological activities being used as analgesic, antipyretic and anti-inflammatory therapeutical drugs (Brogden, 1986; Gursoy et al., 2000). A class of new compounds with the pyrazolone moiety was synthesized and reported for their antibacterial and antifungal activities by Ragavan et al. (2009, 2010). A new pyrazolone derivative, edaravone (3-methyl-1-phenyl-2-pyrazoline-5-one), is being used as a drug in clinical practice for brain ischemia (Watanabe et al., 1984; Kawai et al., 1997) and the same has been found to be effective against myocardial ischemia (Wu et al., 2002).

There are two independent molecules (A and B) in the asymmetric unit (Fig. 1). The maximum deviations in 1H-pyrazole ring (N1/N2/C7–C9) for molecules A and B are 0.006 (2) and 0.011 (2) Å, respectively, at atoms C6A and C6B. The dihedral angles formed between the 1H-pyrazole ring and benzene ring in molecules A and B are 39.57 (14) and 41.95 (13)°, respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to those closely related structures (Shahani et al., 2009, 2010a–c).

In the crystal packing (Fig. 2), pairs of intermolecular O1A—H1OA···N2A and O1B—H1OB···N2B hydrogen bonds (Table 1) form dimers with neighbouring molecules, generating R₂²(8) ring motifs (Bernstein et al., 1995). These dimers are further linked into R₄⁴(10) ring motifs by additional intermolecular N1A—H1NA···O1B and N1B—H1NB···O1A hydrogen bonds (Table 1), forming one dimensional chains along the [101] direction. The crystal structure is further stabilized by C—H···π interaction (Table 1), involving the C1B—C6B benzene ring (centroid Cg1).

Related literature top

For background to the biological activity of 4-methyl-3-phenyl-1H-pyrazol-5-ol, see: Brogden (1986); Gursoy et al. (2000); Ragavan et al. (2009, 2010); Watanabe et al. (1984); Kawai et al. (1997); Wu et al. (2002). For related structures, see: Shahani et al. (2009, 2010a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The compound 4-methyl-5-phenyl-1-H-pyrazol-3-ol has been synthesized using the method available in the literature (Ragavan et al., 2009, 2010) and recrystallized using the ethanol (white solid). m.p. 278.5–493 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 20% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the b axis, showing a one-dimensional chain.

4-Methyl-5-phenyl-1H-pyrazol-3-ol top

Crystal data top

C₁₀H₁₀N₂O	F(000) = 1472
M_r = 174.20	D_x = 1.278 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3052 reflections
a = 26.4082 (19) Å	θ = 3.3–27.2°
b = 11.0972 (8) Å	µ = 0.09 mm⁻¹
c = 14.1245 (10) Å	T = 100 K
β = 118.996 (1)°	Block, colourless
V = 3620.4 (4) Å³	0.35 × 0.14 × 0.08 mm
Z = 16

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5255 independent reflections
Radiation source: fine-focus sealed tube	2907 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→28
T_min = 0.970, T_max = 0.993	k = −15→13
19166 measured reflections	l = −19→19

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0985P)²] where P = (F_o² + 2F_c²)/3
5255 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₀H₁₀N₂O	V = 3620.4 (4) Å³
M_r = 174.20	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 26.4082 (19) Å	µ = 0.09 mm⁻¹
b = 11.0972 (8) Å	T = 100 K
c = 14.1245 (10) Å	0.35 × 0.14 × 0.08 mm
β = 118.996 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5255 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2907 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.993	R_int = 0.049
19166 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.33 e Å⁻³
5255 reflections	Δρ_min = −0.26 e Å⁻³
243 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1A	0.30484 (5)	1.15234 (15)	0.48624 (10)	0.0513 (4)
H1OA	0.3021	1.1865	0.5356	0.077*
N1A	0.17011 (7)	1.19165 (16)	0.26752 (12)	0.0419 (4)
N2A	0.21137 (6)	1.22060 (17)	0.36985 (11)	0.0416 (4)
C1A	0.09436 (9)	1.0463 (3)	0.07114 (18)	0.0643 (7)
H1AA	0.0772	1.0599	0.1142	0.077*
C2A	0.06077 (11)	1.0113 (3)	−0.0353 (2)	0.0835 (10)
H2AA	0.0211	1.0019	−0.0634	0.100*
C3A	0.08503 (12)	0.9902 (3)	−0.09985 (19)	0.0704 (8)
H3AA	0.0621	0.9665	−0.1715	0.084*
C4A	0.14342 (12)	1.0042 (3)	−0.05821 (19)	0.0676 (7)
H4AA	0.1603	0.9906	−0.1017	0.081*
C5A	0.17726 (10)	1.0384 (3)	0.04793 (17)	0.0605 (6)
H5AA	0.2170	1.0462	0.0758	0.073*
C6A	0.15335 (8)	1.06126 (19)	0.11381 (14)	0.0412 (4)
C7A	0.18926 (8)	1.10453 (19)	0.22525 (14)	0.0386 (4)
C8A	0.24504 (8)	1.07398 (19)	0.30334 (14)	0.0406 (4)
C9A	0.25656 (7)	1.1493 (2)	0.39179 (14)	0.0404 (4)
C10A	0.28424 (9)	0.9785 (2)	0.30003 (17)	0.0526 (5)
H10A	0.2662	0.9409	0.2300	0.079*
H10B	0.2914	0.9190	0.3545	0.079*
H10C	0.3202	1.0143	0.3135	0.079*
O1B	−0.05992 (5)	0.70768 (16)	−0.21038 (10)	0.0515 (4)
H1OB	−0.0528	0.7049	−0.2616	0.077*
N1B	0.08261 (7)	0.69465 (18)	−0.01528 (12)	0.0468 (4)
N2B	0.04080 (6)	0.70277 (17)	−0.12057 (12)	0.0455 (4)
C1B	0.14424 (9)	0.7478 (2)	0.21872 (16)	0.0564 (6)
H1BA	0.1524	0.8034	0.1787	0.068*
C2B	0.17998 (11)	0.7390 (3)	0.32909 (18)	0.0725 (8)
H2BA	0.2123	0.7887	0.3631	0.087*
C3B	0.16837 (12)	0.6580 (3)	0.38904 (18)	0.0708 (8)
H3BA	0.1925	0.6531	0.4635	0.085*
C4B	0.12108 (10)	0.5843 (3)	0.33917 (17)	0.0630 (7)
H4BA	0.1134	0.5285	0.3797	0.076*
C5B	0.08471 (9)	0.5923 (2)	0.22872 (16)	0.0520 (5)
H5BA	0.0524	0.5426	0.1954	0.062*
C6B	0.09620 (8)	0.67397 (19)	0.16757 (14)	0.0409 (4)
C7B	0.05896 (8)	0.68061 (19)	0.04958 (14)	0.0400 (4)
C8B	−0.00068 (8)	0.6800 (2)	−0.01460 (14)	0.0411 (5)
C9B	−0.00976 (8)	0.69654 (19)	−0.12047 (14)	0.0406 (4)
C10B	−0.04620 (9)	0.6615 (3)	0.01754 (18)	0.0598 (6)
H10D	−0.0283	0.6528	0.0947	0.090*
H10E	−0.0679	0.5901	−0.0167	0.090*
H10F	−0.0717	0.7298	−0.0047	0.090*
H1NB	0.1235 (11)	0.687 (3)	0.0001 (19)	0.073 (8)*
H1NA	0.1316 (11)	1.224 (2)	0.2420 (18)	0.064 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0298 (6)	0.0806 (12)	0.0370 (7)	0.0088 (6)	0.0112 (5)	−0.0066 (7)
N1A	0.0321 (7)	0.0554 (11)	0.0348 (7)	0.0049 (7)	0.0134 (6)	−0.0018 (7)
N2A	0.0299 (7)	0.0569 (11)	0.0336 (7)	0.0034 (7)	0.0120 (6)	−0.0038 (7)
C1A	0.0429 (11)	0.093 (2)	0.0548 (12)	−0.0142 (12)	0.0221 (10)	−0.0223 (12)
C2A	0.0463 (13)	0.126 (3)	0.0661 (15)	−0.0210 (15)	0.0174 (12)	−0.0364 (17)
C3A	0.0739 (17)	0.079 (2)	0.0488 (12)	−0.0139 (14)	0.0223 (12)	−0.0220 (12)
C4A	0.0755 (16)	0.082 (2)	0.0516 (12)	−0.0043 (14)	0.0357 (12)	−0.0183 (12)
C5A	0.0478 (11)	0.0854 (19)	0.0496 (11)	−0.0037 (12)	0.0245 (10)	−0.0106 (12)
C6A	0.0393 (9)	0.0436 (12)	0.0394 (9)	−0.0020 (8)	0.0180 (8)	−0.0021 (8)
C7A	0.0342 (8)	0.0461 (12)	0.0385 (9)	−0.0015 (8)	0.0199 (7)	−0.0007 (8)
C8A	0.0330 (8)	0.0515 (13)	0.0383 (9)	0.0012 (8)	0.0181 (7)	−0.0002 (8)
C9A	0.0295 (8)	0.0549 (13)	0.0363 (9)	0.0031 (8)	0.0157 (7)	0.0020 (8)
C10A	0.0426 (10)	0.0601 (15)	0.0530 (11)	0.0109 (10)	0.0214 (9)	−0.0005 (10)
O1B	0.0298 (6)	0.0862 (12)	0.0357 (7)	0.0068 (7)	0.0135 (6)	−0.0007 (6)
N1B	0.0305 (8)	0.0740 (14)	0.0338 (7)	−0.0012 (8)	0.0139 (6)	0.0038 (7)
N2B	0.0291 (7)	0.0713 (13)	0.0316 (7)	0.0007 (7)	0.0113 (6)	0.0029 (7)
C1B	0.0556 (12)	0.0620 (16)	0.0418 (10)	−0.0101 (11)	0.0160 (9)	0.0013 (10)
C2B	0.0650 (15)	0.088 (2)	0.0436 (12)	−0.0171 (14)	0.0097 (11)	−0.0075 (12)
C3B	0.0685 (16)	0.102 (2)	0.0352 (10)	0.0073 (15)	0.0196 (11)	0.0036 (12)
C4B	0.0648 (14)	0.0853 (19)	0.0455 (11)	0.0113 (13)	0.0320 (11)	0.0194 (11)
C5B	0.0494 (11)	0.0626 (15)	0.0466 (10)	0.0015 (10)	0.0253 (9)	0.0098 (10)
C6B	0.0398 (9)	0.0474 (12)	0.0349 (8)	0.0043 (8)	0.0176 (8)	0.0034 (8)
C7B	0.0369 (9)	0.0481 (12)	0.0351 (9)	−0.0006 (8)	0.0174 (8)	0.0021 (8)
C8B	0.0338 (9)	0.0519 (13)	0.0384 (9)	−0.0004 (8)	0.0180 (8)	0.0009 (8)
C9B	0.0308 (8)	0.0524 (13)	0.0363 (9)	0.0002 (8)	0.0145 (7)	−0.0011 (8)
C10B	0.0405 (11)	0.0886 (19)	0.0561 (12)	0.0052 (11)	0.0280 (10)	0.0070 (12)

Geometric parameters (Å, º) top

O1A—C9A	1.326 (2)	O1B—C9B	1.323 (2)
O1A—H1OA	0.8273	O1B—H1OB	0.8317
N1A—C7A	1.356 (3)	N1B—C7B	1.345 (2)
N1A—N2A	1.3612 (19)	N1B—N2B	1.359 (2)
N1A—H1NA	0.97 (2)	N1B—H1NB	1.00 (3)
N2A—C9A	1.337 (2)	N2B—C9B	1.338 (2)
C1A—C2A	1.380 (3)	C1B—C2B	1.380 (3)
C1A—C6A	1.381 (3)	C1B—C6B	1.384 (3)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.365 (4)	C2B—C3B	1.368 (4)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.367 (4)	C3B—C4B	1.368 (4)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.375 (3)	C4B—C5B	1.383 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.378 (3)	C5B—C6B	1.383 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.470 (2)	C6B—C7B	1.470 (2)
C7A—C8A	1.388 (2)	C7B—C8B	1.385 (2)
C8A—C9A	1.409 (3)	C8B—C9B	1.407 (3)
C8A—C10A	1.498 (3)	C8B—C10B	1.491 (3)
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600

C9A—O1A—H1OA	115.1	C9B—O1B—H1OB	106.7
C7A—N1A—N2A	111.00 (15)	C7B—N1B—N2B	110.74 (15)
C7A—N1A—H1NA	130.4 (15)	C7B—N1B—H1NB	130.8 (14)
N2A—N1A—H1NA	117.7 (14)	N2B—N1B—H1NB	117.7 (14)
C9A—N2A—N1A	105.76 (15)	C9B—N2B—N1B	106.09 (15)
C2A—C1A—C6A	120.2 (2)	C2B—C1B—C6B	120.0 (2)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	120.0
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	120.0
C3A—C2A—C1A	120.9 (2)	C3B—C2B—C1B	120.7 (2)
C3A—C2A—H2AA	119.5	C3B—C2B—H2BA	119.7
C1A—C2A—H2AA	119.5	C1B—C2B—H2BA	119.7
C2A—C3A—C4A	119.3 (2)	C4B—C3B—C2B	119.8 (2)
C2A—C3A—H3AA	120.3	C4B—C3B—H3BA	120.1
C4A—C3A—H3AA	120.3	C2B—C3B—H3BA	120.1
C3A—C4A—C5A	120.1 (2)	C3B—C4B—C5B	120.2 (2)
C3A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.9
C5A—C4A—H4AA	119.9	C5B—C4B—H4BA	119.9
C4A—C5A—C6A	121.3 (2)	C4B—C5B—C6B	120.3 (2)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.9
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.9
C5A—C6A—C1A	118.19 (18)	C1B—C6B—C5B	119.03 (18)
C5A—C6A—C7A	120.97 (18)	C1B—C6B—C7B	120.16 (18)
C1A—C6A—C7A	120.81 (18)	C5B—C6B—C7B	120.79 (18)
N1A—C7A—C8A	107.63 (16)	N1B—C7B—C8B	108.12 (15)
N1A—C7A—C6A	121.31 (16)	N1B—C7B—C6B	120.11 (16)
C8A—C7A—C6A	131.04 (18)	C8B—C7B—C6B	131.71 (17)
C7A—C8A—C9A	104.45 (17)	C7B—C8B—C9B	104.41 (16)
C7A—C8A—C10A	129.14 (17)	C7B—C8B—C10B	129.08 (17)
C9A—C8A—C10A	126.32 (17)	C9B—C8B—C10B	126.47 (17)
O1A—C9A—N2A	122.24 (17)	O1B—C9B—N2B	121.95 (16)
O1A—C9A—C8A	126.60 (17)	O1B—C9B—C8B	127.43 (17)
N2A—C9A—C8A	111.16 (15)	N2B—C9B—C8B	110.60 (15)
C8A—C10A—H10A	109.5	C8B—C10B—H10D	109.5
C8A—C10A—H10B	109.5	C8B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C8A—C10A—H10C	109.5	C8B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5

C7A—N1A—N2A—C9A	−0.7 (2)	C7B—N1B—N2B—C9B	1.5 (2)
C6A—C1A—C2A—C3A	0.3 (5)	C6B—C1B—C2B—C3B	−0.2 (4)
C1A—C2A—C3A—C4A	0.0 (5)	C1B—C2B—C3B—C4B	0.4 (5)
C2A—C3A—C4A—C5A	0.4 (5)	C2B—C3B—C4B—C5B	−0.7 (4)
C3A—C4A—C5A—C6A	−1.2 (4)	C3B—C4B—C5B—C6B	0.8 (4)
C4A—C5A—C6A—C1A	1.4 (4)	C2B—C1B—C6B—C5B	0.2 (4)
C4A—C5A—C6A—C7A	−176.4 (2)	C2B—C1B—C6B—C7B	−178.2 (2)
C2A—C1A—C6A—C5A	−1.0 (4)	C4B—C5B—C6B—C1B	−0.5 (3)
C2A—C1A—C6A—C7A	176.8 (3)	C4B—C5B—C6B—C7B	178.0 (2)
N2A—N1A—C7A—C8A	0.7 (2)	N2B—N1B—C7B—C8B	−0.3 (2)
N2A—N1A—C7A—C6A	−177.51 (17)	N2B—N1B—C7B—C6B	−177.91 (18)
C5A—C6A—C7A—N1A	138.9 (2)	C1B—C6B—C7B—N1B	39.6 (3)
C1A—C6A—C7A—N1A	−38.9 (3)	C5B—C6B—C7B—N1B	−138.8 (2)
C5A—C6A—C7A—C8A	−38.9 (3)	C1B—C6B—C7B—C8B	−137.3 (2)
C1A—C6A—C7A—C8A	143.3 (2)	C5B—C6B—C7B—C8B	44.2 (3)
N1A—C7A—C8A—C9A	−0.5 (2)	N1B—C7B—C8B—C9B	−0.9 (2)
C6A—C7A—C8A—C9A	177.5 (2)	C6B—C7B—C8B—C9B	176.3 (2)
N1A—C7A—C8A—C10A	176.4 (2)	N1B—C7B—C8B—C10B	177.0 (2)
C6A—C7A—C8A—C10A	−5.6 (4)	C6B—C7B—C8B—C10B	−5.9 (4)
N1A—N2A—C9A—O1A	−179.23 (17)	N1B—N2B—C9B—O1B	176.63 (19)
N1A—N2A—C9A—C8A	0.4 (2)	N1B—N2B—C9B—C8B	−2.1 (2)
C7A—C8A—C9A—O1A	179.64 (19)	C7B—C8B—C9B—O1B	−176.7 (2)
C10A—C8A—C9A—O1A	2.7 (3)	C10B—C8B—C9B—O1B	5.3 (4)
C7A—C8A—C9A—N2A	0.1 (2)	C7B—C8B—C9B—N2B	1.9 (2)
C10A—C8A—C9A—N2A	−176.89 (19)	C10B—C8B—C9B—N2B	−176.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1B–C6B benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N2Aⁱ	0.83	1.85	2.673 (2)	171
O1B—H1OB···N2Bⁱⁱ	0.83	1.84	2.670 (2)	177
N1B—H1NB···O1Aⁱⁱⁱ	1.00 (3)	1.85 (3)	2.836 (3)	171 (3)
N1A—H1NA···O1B^iv	0.97 (3)	1.88 (3)	2.844 (2)	173 (2)
C10A—H10C···Cg1^v	0.96	2.77	3.575 (3)	142

Symmetry codes: (i) −x+1/2, −y+5/2, −z+1; (ii) −x, y, −z−1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x, −y+2, −z; (v) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂O
M_r	174.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	26.4082 (19), 11.0972 (8), 14.1245 (10)
β (°)	118.996 (1)
V (Å³)	3620.4 (4)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.970, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	19166, 5255, 2907
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.204, 1.13
No. of reflections	5255
No. of parameters	243
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1B–C6B benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N2Aⁱ	0.83	1.85	2.673 (2)	171
O1B—H1OB···N2Bⁱⁱ	0.83	1.84	2.670 (2)	177
N1B—H1NB···O1Aⁱⁱⁱ	1.00 (3)	1.85 (3)	2.836 (3)	171 (3)
N1A—H1NA···O1B^iv	0.97 (3)	1.88 (3)	2.844 (2)	173 (2)
C10A—H10C···Cg1^v	0.96	2.77	3.575 (3)	142

Symmetry codes: (i) −x+1/2, −y+5/2, −z+1; (ii) −x, y, −z−1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x, −y+2, −z; (v) x, −y, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

TSH and HKF thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012) for the position of Graduate Research Assistant. VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

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Volume 66| Part 7| July 2010| Pages o1697-o1698

doi:10.1107/S1600536810022828

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