organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 7| July 2010| Pages o1697-o1698

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

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[Brogden, R. N. (1986). Pyrazolone Derivatives Drugs, 32, 60-70.]); Gursoy et al. (2000[Gursoy, A., Demirayak, S., Capan, G., Erol, K. & Vural, K. (2000). Eur. J. Med. Chem. 35, 359-364.]); Ragavan et al. (2009[Ragavan, R. V., Vijayakumar, V. & Kumari, N. S. (2009). Eur. J. Med. Chem. 44, 3852-3857.], 2010[Ragavan, R. V., Vijayakumar, V. & Kumari, N. S. (2010). Eur. J. Med. Chem. 45, 1173-1180.]); Watanabe et al. (1984[Watanabe, T., Yuki, S., Egawa, M. & Nishi, H. (1984). J. Pharmacol. Exp. Ther. 268, 1597-1604.]); Kawai et al. (1997[Kawai, H., Nakai, H., Suga, M., Yuki, S., Watanabe, T. & Saito, K. I. (1997). J. Pharmcol. Exp. Ther. 281, 921-927.]); Wu et al. (2002[Wu, T. W., Zeng, L. H., Wu, J. & Fung, K. P. (2002). Life Sci. 71, 2249-2255.]). For related structures, see: Shahani et al. (2009[Shahani, T., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2009). Acta Cryst. E65, o3249-o3250.], 2010a[Shahani, T., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2010a). Acta Cryst. E66, o142-o143.],b[Shahani, T., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2010b). Acta Cryst. E66, o1357-o1358.],c[Shahani, T., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2010c). Acta Cryst. E66, o1482-o1483.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C10H10N2O

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wiscosin, USA.]) Tmin = 0.970, Tmax = 0.993

  • 19166 measured reflections

  • 5255 independent reflections

  • 2907 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.33 e Å−3

  • Δρmin = −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 DA 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⋯O1Biv 0.97 (3) 1.88 (3) 2.844 (2) 173 (2)
C10A—H10CCg1v 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wiscosin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wiscosin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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, 2010ac).

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.

Refinement top

The H atoms bound to O atoms were located in a difference map and constrained to ride with their parent atoms, with Uiso(H) = 1.5Ueq(O) (O—H = 0.83 Å). The H atoms bound to N atoms were located in a difference map and were refined freely [refined N—H lengths, 1.00 (3) and 0.97 (2) Å]. All other H atoms were positioned geometrically (C—H = 0.93–0.96 Å], with Uiso(H) = 1.2 or 1.5Ueq(C).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 20% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] 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
C10H10N2OF(000) = 1472
Mr = 174.20Dx = 1.278 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3052 reflections
a = 26.4082 (19) Åθ = 3.3–27.2°
b = 11.0972 (8) ŵ = 0.09 mm1
c = 14.1245 (10) ÅT = 100 K
β = 118.996 (1)°Block, colourless
V = 3620.4 (4) Å30.35 × 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 tube2907 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scansθmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 3728
Tmin = 0.970, Tmax = 0.993k = 1513
19166 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0985P)2]
where P = (Fo2 + 2Fc2)/3
5255 reflections(Δ/σ)max = 0.001
243 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C10H10N2OV = 3620.4 (4) Å3
Mr = 174.20Z = 16
Monoclinic, C2/cMo Kα radiation
a = 26.4082 (19) ŵ = 0.09 mm1
b = 11.0972 (8) ÅT = 100 K
c = 14.1245 (10) Å0.35 × 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)
Tmin = 0.970, Tmax = 0.993Rint = 0.049
19166 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.204H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.33 e Å3
5255 reflectionsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
O1A0.30484 (5)1.15234 (15)0.48624 (10)0.0513 (4)
H1OA0.30211.18650.53560.077*
N1A0.17011 (7)1.19165 (16)0.26752 (12)0.0419 (4)
N2A0.21137 (6)1.22060 (17)0.36985 (11)0.0416 (4)
C1A0.09436 (9)1.0463 (3)0.07114 (18)0.0643 (7)
H1AA0.07721.05990.11420.077*
C2A0.06077 (11)1.0113 (3)0.0353 (2)0.0835 (10)
H2AA0.02111.00190.06340.100*
C3A0.08503 (12)0.9902 (3)0.09985 (19)0.0704 (8)
H3AA0.06210.96650.17150.084*
C4A0.14342 (12)1.0042 (3)0.05821 (19)0.0676 (7)
H4AA0.16030.99060.10170.081*
C5A0.17726 (10)1.0384 (3)0.04793 (17)0.0605 (6)
H5AA0.21701.04620.07580.073*
C6A0.15335 (8)1.06126 (19)0.11381 (14)0.0412 (4)
C7A0.18926 (8)1.10453 (19)0.22525 (14)0.0386 (4)
C8A0.24504 (8)1.07398 (19)0.30334 (14)0.0406 (4)
C9A0.25656 (7)1.1493 (2)0.39179 (14)0.0404 (4)
C10A0.28424 (9)0.9785 (2)0.30003 (17)0.0526 (5)
H10A0.26620.94090.23000.079*
H10B0.29140.91900.35450.079*
H10C0.32021.01430.31350.079*
O1B0.05992 (5)0.70768 (16)0.21038 (10)0.0515 (4)
H1OB0.05280.70490.26160.077*
N1B0.08261 (7)0.69465 (18)0.01528 (12)0.0468 (4)
N2B0.04080 (6)0.70277 (17)0.12057 (12)0.0455 (4)
C1B0.14424 (9)0.7478 (2)0.21872 (16)0.0564 (6)
H1BA0.15240.80340.17870.068*
C2B0.17998 (11)0.7390 (3)0.32909 (18)0.0725 (8)
H2BA0.21230.78870.36310.087*
C3B0.16837 (12)0.6580 (3)0.38904 (18)0.0708 (8)
H3BA0.19250.65310.46350.085*
C4B0.12108 (10)0.5843 (3)0.33917 (17)0.0630 (7)
H4BA0.11340.52850.37970.076*
C5B0.08471 (9)0.5923 (2)0.22872 (16)0.0520 (5)
H5BA0.05240.54260.19540.062*
C6B0.09620 (8)0.67397 (19)0.16757 (14)0.0409 (4)
C7B0.05896 (8)0.68061 (19)0.04958 (14)0.0400 (4)
C8B0.00068 (8)0.6800 (2)0.01460 (14)0.0411 (5)
C9B0.00976 (8)0.69654 (19)0.12047 (14)0.0406 (4)
C10B0.04620 (9)0.6615 (3)0.01754 (18)0.0598 (6)
H10D0.02830.65280.09470.090*
H10E0.06790.59010.01670.090*
H10F0.07170.72980.00470.090*
H1NB0.1235 (11)0.687 (3)0.0001 (19)0.073 (8)*
H1NA0.1316 (11)1.224 (2)0.2420 (18)0.064 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0298 (6)0.0806 (12)0.0370 (7)0.0088 (6)0.0112 (5)0.0066 (7)
N1A0.0321 (7)0.0554 (11)0.0348 (7)0.0049 (7)0.0134 (6)0.0018 (7)
N2A0.0299 (7)0.0569 (11)0.0336 (7)0.0034 (7)0.0120 (6)0.0038 (7)
C1A0.0429 (11)0.093 (2)0.0548 (12)0.0142 (12)0.0221 (10)0.0223 (12)
C2A0.0463 (13)0.126 (3)0.0661 (15)0.0210 (15)0.0174 (12)0.0364 (17)
C3A0.0739 (17)0.079 (2)0.0488 (12)0.0139 (14)0.0223 (12)0.0220 (12)
C4A0.0755 (16)0.082 (2)0.0516 (12)0.0043 (14)0.0357 (12)0.0183 (12)
C5A0.0478 (11)0.0854 (19)0.0496 (11)0.0037 (12)0.0245 (10)0.0106 (12)
C6A0.0393 (9)0.0436 (12)0.0394 (9)0.0020 (8)0.0180 (8)0.0021 (8)
C7A0.0342 (8)0.0461 (12)0.0385 (9)0.0015 (8)0.0199 (7)0.0007 (8)
C8A0.0330 (8)0.0515 (13)0.0383 (9)0.0012 (8)0.0181 (7)0.0002 (8)
C9A0.0295 (8)0.0549 (13)0.0363 (9)0.0031 (8)0.0157 (7)0.0020 (8)
C10A0.0426 (10)0.0601 (15)0.0530 (11)0.0109 (10)0.0214 (9)0.0005 (10)
O1B0.0298 (6)0.0862 (12)0.0357 (7)0.0068 (7)0.0135 (6)0.0007 (6)
N1B0.0305 (8)0.0740 (14)0.0338 (7)0.0012 (8)0.0139 (6)0.0038 (7)
N2B0.0291 (7)0.0713 (13)0.0316 (7)0.0007 (7)0.0113 (6)0.0029 (7)
C1B0.0556 (12)0.0620 (16)0.0418 (10)0.0101 (11)0.0160 (9)0.0013 (10)
C2B0.0650 (15)0.088 (2)0.0436 (12)0.0171 (14)0.0097 (11)0.0075 (12)
C3B0.0685 (16)0.102 (2)0.0352 (10)0.0073 (15)0.0196 (11)0.0036 (12)
C4B0.0648 (14)0.0853 (19)0.0455 (11)0.0113 (13)0.0320 (11)0.0194 (11)
C5B0.0494 (11)0.0626 (15)0.0466 (10)0.0015 (10)0.0253 (9)0.0098 (10)
C6B0.0398 (9)0.0474 (12)0.0349 (8)0.0043 (8)0.0176 (8)0.0034 (8)
C7B0.0369 (9)0.0481 (12)0.0351 (9)0.0006 (8)0.0174 (8)0.0021 (8)
C8B0.0338 (9)0.0519 (13)0.0384 (9)0.0004 (8)0.0180 (8)0.0009 (8)
C9B0.0308 (8)0.0524 (13)0.0363 (9)0.0002 (8)0.0145 (7)0.0011 (8)
C10B0.0405 (11)0.0886 (19)0.0561 (12)0.0052 (11)0.0280 (10)0.0070 (12)
Geometric parameters (Å, º) top
O1A—C9A1.326 (2)O1B—C9B1.323 (2)
O1A—H1OA0.8273O1B—H1OB0.8317
N1A—C7A1.356 (3)N1B—C7B1.345 (2)
N1A—N2A1.3612 (19)N1B—N2B1.359 (2)
N1A—H1NA0.97 (2)N1B—H1NB1.00 (3)
N2A—C9A1.337 (2)N2B—C9B1.338 (2)
C1A—C2A1.380 (3)C1B—C2B1.380 (3)
C1A—C6A1.381 (3)C1B—C6B1.384 (3)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.365 (4)C2B—C3B1.368 (4)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.367 (4)C3B—C4B1.368 (4)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.375 (3)C4B—C5B1.383 (3)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.378 (3)C5B—C6B1.383 (3)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.470 (2)C6B—C7B1.470 (2)
C7A—C8A1.388 (2)C7B—C8B1.385 (2)
C8A—C9A1.409 (3)C8B—C9B1.407 (3)
C8A—C10A1.498 (3)C8B—C10B1.491 (3)
C10A—H10A0.9600C10B—H10D0.9600
C10A—H10B0.9600C10B—H10E0.9600
C10A—H10C0.9600C10B—H10F0.9600
C9A—O1A—H1OA115.1C9B—O1B—H1OB106.7
C7A—N1A—N2A111.00 (15)C7B—N1B—N2B110.74 (15)
C7A—N1A—H1NA130.4 (15)C7B—N1B—H1NB130.8 (14)
N2A—N1A—H1NA117.7 (14)N2B—N1B—H1NB117.7 (14)
C9A—N2A—N1A105.76 (15)C9B—N2B—N1B106.09 (15)
C2A—C1A—C6A120.2 (2)C2B—C1B—C6B120.0 (2)
C2A—C1A—H1AA119.9C2B—C1B—H1BA120.0
C6A—C1A—H1AA119.9C6B—C1B—H1BA120.0
C3A—C2A—C1A120.9 (2)C3B—C2B—C1B120.7 (2)
C3A—C2A—H2AA119.5C3B—C2B—H2BA119.7
C1A—C2A—H2AA119.5C1B—C2B—H2BA119.7
C2A—C3A—C4A119.3 (2)C4B—C3B—C2B119.8 (2)
C2A—C3A—H3AA120.3C4B—C3B—H3BA120.1
C4A—C3A—H3AA120.3C2B—C3B—H3BA120.1
C3A—C4A—C5A120.1 (2)C3B—C4B—C5B120.2 (2)
C3A—C4A—H4AA119.9C3B—C4B—H4BA119.9
C5A—C4A—H4AA119.9C5B—C4B—H4BA119.9
C4A—C5A—C6A121.3 (2)C4B—C5B—C6B120.3 (2)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.9
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.9
C5A—C6A—C1A118.19 (18)C1B—C6B—C5B119.03 (18)
C5A—C6A—C7A120.97 (18)C1B—C6B—C7B120.16 (18)
C1A—C6A—C7A120.81 (18)C5B—C6B—C7B120.79 (18)
N1A—C7A—C8A107.63 (16)N1B—C7B—C8B108.12 (15)
N1A—C7A—C6A121.31 (16)N1B—C7B—C6B120.11 (16)
C8A—C7A—C6A131.04 (18)C8B—C7B—C6B131.71 (17)
C7A—C8A—C9A104.45 (17)C7B—C8B—C9B104.41 (16)
C7A—C8A—C10A129.14 (17)C7B—C8B—C10B129.08 (17)
C9A—C8A—C10A126.32 (17)C9B—C8B—C10B126.47 (17)
O1A—C9A—N2A122.24 (17)O1B—C9B—N2B121.95 (16)
O1A—C9A—C8A126.60 (17)O1B—C9B—C8B127.43 (17)
N2A—C9A—C8A111.16 (15)N2B—C9B—C8B110.60 (15)
C8A—C10A—H10A109.5C8B—C10B—H10D109.5
C8A—C10A—H10B109.5C8B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
C8A—C10A—H10C109.5C8B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
C7A—N1A—N2A—C9A0.7 (2)C7B—N1B—N2B—C9B1.5 (2)
C6A—C1A—C2A—C3A0.3 (5)C6B—C1B—C2B—C3B0.2 (4)
C1A—C2A—C3A—C4A0.0 (5)C1B—C2B—C3B—C4B0.4 (5)
C2A—C3A—C4A—C5A0.4 (5)C2B—C3B—C4B—C5B0.7 (4)
C3A—C4A—C5A—C6A1.2 (4)C3B—C4B—C5B—C6B0.8 (4)
C4A—C5A—C6A—C1A1.4 (4)C2B—C1B—C6B—C5B0.2 (4)
C4A—C5A—C6A—C7A176.4 (2)C2B—C1B—C6B—C7B178.2 (2)
C2A—C1A—C6A—C5A1.0 (4)C4B—C5B—C6B—C1B0.5 (3)
C2A—C1A—C6A—C7A176.8 (3)C4B—C5B—C6B—C7B178.0 (2)
N2A—N1A—C7A—C8A0.7 (2)N2B—N1B—C7B—C8B0.3 (2)
N2A—N1A—C7A—C6A177.51 (17)N2B—N1B—C7B—C6B177.91 (18)
C5A—C6A—C7A—N1A138.9 (2)C1B—C6B—C7B—N1B39.6 (3)
C1A—C6A—C7A—N1A38.9 (3)C5B—C6B—C7B—N1B138.8 (2)
C5A—C6A—C7A—C8A38.9 (3)C1B—C6B—C7B—C8B137.3 (2)
C1A—C6A—C7A—C8A143.3 (2)C5B—C6B—C7B—C8B44.2 (3)
N1A—C7A—C8A—C9A0.5 (2)N1B—C7B—C8B—C9B0.9 (2)
C6A—C7A—C8A—C9A177.5 (2)C6B—C7B—C8B—C9B176.3 (2)
N1A—C7A—C8A—C10A176.4 (2)N1B—C7B—C8B—C10B177.0 (2)
C6A—C7A—C8A—C10A5.6 (4)C6B—C7B—C8B—C10B5.9 (4)
N1A—N2A—C9A—O1A179.23 (17)N1B—N2B—C9B—O1B176.63 (19)
N1A—N2A—C9A—C8A0.4 (2)N1B—N2B—C9B—C8B2.1 (2)
C7A—C8A—C9A—O1A179.64 (19)C7B—C8B—C9B—O1B176.7 (2)
C10A—C8A—C9A—O1A2.7 (3)C10B—C8B—C9B—O1B5.3 (4)
C7A—C8A—C9A—N2A0.1 (2)C7B—C8B—C9B—N2B1.9 (2)
C10A—C8A—C9A—N2A176.89 (19)C10B—C8B—C9B—N2B176.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1B–C6B benzene ring.
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···N2Ai0.831.852.673 (2)171
O1B—H1OB···N2Bii0.831.842.670 (2)177
N1B—H1NB···O1Aiii1.00 (3)1.85 (3)2.836 (3)171 (3)
N1A—H1NA···O1Biv0.97 (3)1.88 (3)2.844 (2)173 (2)
C10A—H10C···Cg1v0.962.773.575 (3)142
Symmetry codes: (i) x+1/2, y+5/2, z+1; (ii) x, y, z1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x, y+2, z; (v) x, y, z1/2.

Experimental details

Crystal data
Chemical formulaC10H10N2O
Mr174.20
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)26.4082 (19), 11.0972 (8), 14.1245 (10)
β (°) 118.996 (1)
V3)3620.4 (4)
Z16
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.35 × 0.14 × 0.08
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.970, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
19166, 5255, 2907
Rint0.049
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.204, 1.13
No. of reflections5255
No. of parameters243
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1A—H1OA···N2Ai0.831.852.673 (2)171
O1B—H1OB···N2Bii0.831.842.670 (2)177
N1B—H1NB···O1Aiii1.00 (3)1.85 (3)2.836 (3)171 (3)
N1A—H1NA···O1Biv0.97 (3)1.88 (3)2.844 (2)173 (2)
C10A—H10C···Cg1v0.962.773.575 (3)142
Symmetry codes: (i) x+1/2, y+5/2, z+1; (ii) x, y, z1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x, y+2, z; (v) x, y, z1/2.
 

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).

References

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