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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 1| January 2011| Pages o151-o152
https://doi.org/10.1107/S160053681005213X

4-Methyl-5-phenyl-1H-pyrazol-3(2H)-one

Wan-Sin Loh,a‡ Hoong-Kun Fun,a*§ R. Venkat Ragavan,b V. Vijayakumarb and S. Sarveswarib

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 December 2010; accepted 12 December 2010; online 18 December 2010)

The asymmetric unit of the title compound, C10H10N2O, contains two crystallographically independent mol­ecules with similar geometries, which exist in the keto form. The C=O bond lengths are 1.2878 (12) Å in mol­ecule A and 1.2890 (12) Å in mol­ecule B, indicating that the compound undergoes enol-to-keto tautomerism during the crystallization process. In mol­ecule A, the pyrazole ring is approximately planar [maximum deviation = 0.007 (1) Å] and forms a dihedral angle of 36.67 (6)° with the attached phenyl ring. In mol­ecule B, the dihedral angle formed between the pyrazole ring [maximum deviation = 0.017 (1) Å] and the phenyl ring is 41.19 (6)°. In the crystal, inter­molecular N—H⋯O hydrogen bonds link neighbouring mol­ecules into dimers generating R22(8) ring motifs. These dimers are linked into ribbons along [101] via inter­molecular N—H⋯O hydrogen bonds, forming R42(10) ring motifs.

Related literature

For background to pyrazole derivatives and their anti­microbial activity, see: Ragavan et al. (2009[Ragavan, R. V., Vijayakumar, V. & Sucheta Kumari, N. (2009). Eur. J. Med. Chem. 44, 3852-3857.], 2010[Ragavan, R. V., Vijayakumar, V. & Sucheta Kumari, N. (2010). Eur. J. Med. Chem. 45, 1173-1180.]). 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 structure of the enol form of this mol­ecule, see: Shahani et al. (2010[Shahani, T., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2010). Acta Cryst. E66, o1697-o1698.]). For other related structures, see: Loh et al. (2010a[Loh, W.-S., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2010a). Acta Cryst. E66, o2925.],b[Loh, W.-S., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Venkatesh, M. (2010b). Acta Cryst. E66, o2563-o2564.],c[Loh, W.-S., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Venkatesh, M. (2010c). Acta Cryst. E66, o3050-o3051.]). 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 the stability of the temperature controller used in 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 = 25.9337 (4) Å

  • b = 10.8100 (1) Å

  • c = 14.1426 (2) Å

  • β = 118.961 (1)°

  • V = 3468.98 (8) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.45 × 0.39 × 0.25 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEXII, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.961, Tmax = 0.978

  • 36992 measured reflections

  • 5087 independent reflections

  • 4389 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.119

  • S = 1.03

  • 5087 reflections

  • 253 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1B—H1NB⋯O1Ai 0.913 (17) 1.796 (17) 2.7001 (11) 170.0 (16)
N1A—H1NA⋯O1B 0.935 (19) 1.78 (2) 2.6987 (14) 165.9 (16)
N2A—H2NA⋯O1Aii 0.93 (2) 1.768 (19) 2.6917 (12) 173.9 (17)
N2B—H2NB⋯O1Biii 0.934 (18) 1.752 (18) 2.6850 (13) 177.0 (16)
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (iii) [-x+1, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEXII, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEXII, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681005213X/sj5074sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681005213X/sj5074Isup2.hkl

checkCIF report


Comment top

Antibacterial and antifungal activities of the azoles are most widely studied and some of them are in clinical practice as anti-microbial agents. However, the azole-resistant strains have led to the development of new anti-microbial compounds. In particular, pyrazole derivatives are extensively studied and used as anti-microbial agents. Pyrazoles represent an important class of heterocyclic compounds and many pyrazole derivatives are reported to have a broad spectrum of biological properties such as anti-inflammatory, antifungal, herbicidal, anti-tumour, cytotoxic, molecular modelling and antiviral activities. Pyrazole derivatives also act as anti-angiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists as well as kinase inhibitors for the treatment of type 2 diabetes, hyperlipidemia, obesity and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules plays an important role in enhancing their biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryls of 1,5-diaryl pyrazoles. These properties and applications are discussed in our previous reports on the synthesis of novel pyrazole derivatives and their microbial activities (Ragavan et al., 2009, 2010). The enol-form of this compound has been already reported in the literature (Shahani et al., 2010).

The title compound (Fig. 1), consists of two crystallographically independent molecules, with similar geometries and exists in the keto-form. This indicates that the compound undergoes an enol-to-keto tautomerism during the crystallization process with the bond length of C═O being 1.2878 (12) Å in molecule A and 1.2890 (12) Å in molecule B. In molecule A, the pyrazole ring (N1A/N2A/C7A–C9A) is approximately planar (maximum deviation of 0.007 (1) Å at N1A) and forms a dihedral angle of 36.67 (6)° with the attached phenyl ring (C1A–C6A). In molecule B, the dihedral angle formed between the pyrazole ring (N1B/N2B/C7B–C9B) [maximum deviation of 0.017 (1) Å at C9B] and the phenyl ring (C1B–C6B) is 41.19 (6)°. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Loh et al., 2010a,b,c).

In the crystal packing (Fig. 2), intermolecular N2A—H2NA···O1A and N2B—H2NB···O1B hydrogen bonds (Table 1) link the neighbouring molecules to form dimers, generating R22(8) ring motifs (Bernstein et al., 1995). These set of dimers are linked into ribbons along the [101], via intermolecular N1A—H1NA···O1B and N1B—H1NB···O1A hydrogen bonds (Table 1), forming R42(10) ring motifs (Bernstein et al., 1995).

Related literature top

For background to pyrazole derivatives and their antimicrobial activity, see: Ragavan et al. (2009, 2010). For bond-length data, see: Allen et al. (1987). For the structure of the enol form of this molecule, see: Shahani et al. (2010). For other related structures, see: Loh et al. (2010a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The compound was synthesized using a literature method (Ragavan et al., 2009, 2010) and recrystallized from ethanol-chloroform; 1:1. M. p.: 493–494 K, yield: 72%.

Refinement top

N– bound H atoms were located from a difference Fourier map and refined freely [N–H = 0.913 (17) to 0.935 (16) Å]. The remaining H atoms were positioned geometrically with bond lengths C–H = 0.93 to 0.96 Å and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups.

Structure description top

Antibacterial and antifungal activities of the azoles are most widely studied and some of them are in clinical practice as anti-microbial agents. However, the azole-resistant strains have led to the development of new anti-microbial compounds. In particular, pyrazole derivatives are extensively studied and used as anti-microbial agents. Pyrazoles represent an important class of heterocyclic compounds and many pyrazole derivatives are reported to have a broad spectrum of biological properties such as anti-inflammatory, antifungal, herbicidal, anti-tumour, cytotoxic, molecular modelling and antiviral activities. Pyrazole derivatives also act as anti-angiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists as well as kinase inhibitors for the treatment of type 2 diabetes, hyperlipidemia, obesity and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules plays an important role in enhancing their biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryls of 1,5-diaryl pyrazoles. These properties and applications are discussed in our previous reports on the synthesis of novel pyrazole derivatives and their microbial activities (Ragavan et al., 2009, 2010). The enol-form of this compound has been already reported in the literature (Shahani et al., 2010).

The title compound (Fig. 1), consists of two crystallographically independent molecules, with similar geometries and exists in the keto-form. This indicates that the compound undergoes an enol-to-keto tautomerism during the crystallization process with the bond length of C═O being 1.2878 (12) Å in molecule A and 1.2890 (12) Å in molecule B. In molecule A, the pyrazole ring (N1A/N2A/C7A–C9A) is approximately planar (maximum deviation of 0.007 (1) Å at N1A) and forms a dihedral angle of 36.67 (6)° with the attached phenyl ring (C1A–C6A). In molecule B, the dihedral angle formed between the pyrazole ring (N1B/N2B/C7B–C9B) [maximum deviation of 0.017 (1) Å at C9B] and the phenyl ring (C1B–C6B) is 41.19 (6)°. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Loh et al., 2010a,b,c).

In the crystal packing (Fig. 2), intermolecular N2A—H2NA···O1A and N2B—H2NB···O1B hydrogen bonds (Table 1) link the neighbouring molecules to form dimers, generating R22(8) ring motifs (Bernstein et al., 1995). These set of dimers are linked into ribbons along the [101], via intermolecular N1A—H1NA···O1B and N1B—H1NB···O1A hydrogen bonds (Table 1), forming R42(10) ring motifs (Bernstein et al., 1995).

For background to pyrazole derivatives and their antimicrobial activity, see: Ragavan et al. (2009, 2010). For bond-length data, see: Allen et al. (1987). For the structure of the enol form of this molecule, see: Shahani et al. (2010). For other related structures, see: Loh et al. (2010a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the b axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.
4-Methyl-5-phenyl-1H-pyrazol-3(2H)-one top
Crystal data top
C10H10N2OF(000) = 1472
Mr = 174.20Dx = 1.334 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9946 reflections
a = 25.9337 (4) Åθ = 2.4–30.1°
b = 10.8100 (1) ŵ = 0.09 mm−1
c = 14.1426 (2) ÅT = 100 K
β = 118.961 (1)°Block, colourless
V = 3468.98 (8) Å30.45 × 0.39 × 0.25 mm
Z = 16
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5087 independent reflections
Radiation source: fine-focus sealed tube4389 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −36→36
Tmin = 0.961, Tmax = 0.978k = −15→15
36992 measured reflectionsl = −19→18
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0684P)2 + 2.050P]
where P = (Fo2 + 2Fc2)/3
5087 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.45 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C10H10N2OV = 3468.98 (8) Å3
Mr = 174.20Z = 16
Monoclinic, C2/cMo Kα radiation
a = 25.9337 (4) ŵ = 0.09 mm−1
b = 10.8100 (1) ÅT = 100 K
c = 14.1426 (2) Å0.45 × 0.39 × 0.25 mm
β = 118.961 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5087 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		4389 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.978Rint = 0.036
36992 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.45 e Å−3
5087 reflectionsΔρmin = −0.22 e Å−3
253 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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
O1A0.19371 (3)0.15583 (7)0.01430 (6)0.01628 (16)
N1A0.33170 (4)0.19356 (8)0.23566 (7)0.01429 (17)
N2A0.28884 (4)0.22212 (8)0.13372 (7)0.01378 (17)
C1A0.40804 (5)0.05241 (11)0.43463 (9)0.0198 (2)
H1AA0.42620.06810.39310.024*
C2A0.44188 (5)0.02010 (12)0.54257 (10)0.0249 (2)
H2AA0.48260.01470.57300.030*
C3A0.41532 (5)−0.00418 (11)0.60540 (10)0.0222 (2)
H3AA0.4382−0.02510.67790.027*
C4A0.35439 (5)0.00296 (10)0.55947 (9)0.0209 (2)
H4AA0.3364−0.01390.60120.025*
C5A0.32019 (5)0.03512 (10)0.45141 (9)0.0188 (2)
H5AA0.27940.03910.42110.023*
C6A0.34665 (4)0.06155 (9)0.38784 (8)0.01417 (19)
C7A0.31075 (4)0.10488 (9)0.27595 (8)0.01305 (19)
C8A0.25384 (4)0.07360 (9)0.19815 (8)0.01399 (19)
C9A0.24055 (4)0.14984 (9)0.10712 (8)0.01324 (19)
C10A0.21385 (4)−0.02449 (10)0.20107 (9)0.0171 (2)
H10A0.2367−0.09580.23850.026*
H10B0.1855−0.04720.12860.026*
H10C0.19370.00660.23800.026*
O1B0.43937 (3)0.28341 (7)0.28820 (6)0.01641 (16)
N1B0.58492 (4)0.29961 (8)0.48713 (7)0.01537 (18)
N2B0.54157 (4)0.29083 (8)0.38216 (7)0.01525 (18)
C1B0.64581 (5)0.25037 (10)0.72121 (9)0.0177 (2)
H1BA0.65490.19290.68250.021*
C2B0.68154 (5)0.26106 (11)0.83201 (9)0.0225 (2)
H2BA0.71440.21020.86760.027*
C3B0.66848 (5)0.34762 (12)0.89026 (10)0.0233 (2)
H3BA0.69260.35490.96450.028*
C4B0.61925 (5)0.42316 (11)0.83712 (9)0.0208 (2)
H4BA0.61070.48160.87580.025*
C5B0.58278 (5)0.41160 (10)0.72656 (9)0.0168 (2)
H5BA0.54940.46100.69160.020*
C6B0.59605 (4)0.32598 (9)0.66741 (8)0.01363 (19)
C7B0.55927 (4)0.31664 (9)0.54975 (8)0.01354 (19)
C8B0.49830 (4)0.31808 (9)0.48467 (8)0.01383 (19)
C9B0.48786 (4)0.29746 (9)0.37751 (8)0.01359 (19)
C10B0.45201 (4)0.34052 (10)0.51676 (9)0.0184 (2)
H10D0.46270.29910.58380.028*
H10E0.41490.30910.46170.028*
H10F0.44870.42770.52540.028*
H1NB0.6234 (7)0.3100 (16)0.5038 (13)0.034 (4)*
H1NA0.3696 (7)0.2271 (15)0.2649 (13)0.030 (4)*
H2NA0.2954 (8)0.2691 (17)0.0857 (14)0.042 (5)*
H2NB0.5490 (7)0.2858 (15)0.3239 (13)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0111 (3)0.0236 (4)0.0122 (4)−0.0017 (3)0.0041 (3)0.0009 (3)
N1A0.0108 (4)0.0179 (4)0.0116 (4)−0.0012 (3)0.0034 (3)0.0017 (3)
N2A0.0099 (4)0.0182 (4)0.0109 (4)−0.0012 (3)0.0031 (3)0.0018 (3)
C1A0.0151 (5)0.0252 (5)0.0193 (6)0.0041 (4)0.0084 (4)0.0052 (4)
C2A0.0156 (5)0.0334 (6)0.0210 (6)0.0065 (4)0.0051 (4)0.0075 (5)
C3A0.0239 (5)0.0223 (5)0.0155 (5)0.0037 (4)0.0057 (4)0.0052 (4)
C4A0.0249 (5)0.0220 (5)0.0180 (5)0.0000 (4)0.0122 (5)0.0030 (4)
C5A0.0163 (5)0.0224 (5)0.0179 (5)−0.0006 (4)0.0083 (4)0.0020 (4)
C6A0.0138 (4)0.0135 (4)0.0135 (5)0.0002 (3)0.0053 (4)0.0003 (3)
C7A0.0117 (4)0.0148 (4)0.0128 (5)0.0005 (3)0.0061 (4)0.0005 (3)
C8A0.0121 (4)0.0157 (4)0.0143 (5)−0.0006 (3)0.0065 (4)−0.0001 (3)
C9A0.0102 (4)0.0165 (4)0.0128 (5)−0.0005 (3)0.0054 (4)−0.0010 (3)
C10A0.0145 (4)0.0183 (5)0.0176 (5)−0.0039 (3)0.0071 (4)0.0001 (4)
O1B0.0108 (3)0.0237 (4)0.0127 (4)−0.0020 (3)0.0041 (3)−0.0001 (3)
N1B0.0097 (4)0.0232 (4)0.0108 (4)−0.0011 (3)0.0030 (3)−0.0021 (3)
N2B0.0110 (4)0.0226 (4)0.0110 (4)−0.0009 (3)0.0044 (3)−0.0014 (3)
C1B0.0163 (4)0.0181 (5)0.0158 (5)0.0025 (4)0.0056 (4)0.0000 (4)
C2B0.0198 (5)0.0258 (5)0.0163 (6)0.0041 (4)0.0042 (4)0.0042 (4)
C3B0.0227 (5)0.0324 (6)0.0121 (5)−0.0028 (4)0.0062 (4)−0.0006 (4)
C4B0.0222 (5)0.0254 (5)0.0177 (5)−0.0039 (4)0.0119 (4)−0.0056 (4)
C5B0.0151 (4)0.0192 (5)0.0160 (5)0.0003 (3)0.0073 (4)−0.0017 (4)
C6B0.0121 (4)0.0155 (4)0.0118 (5)−0.0014 (3)0.0046 (4)−0.0004 (3)
C7B0.0127 (4)0.0142 (4)0.0130 (5)0.0005 (3)0.0056 (4)−0.0004 (3)
C8B0.0123 (4)0.0157 (4)0.0131 (5)0.0001 (3)0.0058 (4)0.0002 (3)
C9B0.0116 (4)0.0141 (4)0.0146 (5)−0.0004 (3)0.0060 (4)0.0006 (3)
C10B0.0141 (4)0.0243 (5)0.0182 (5)−0.0004 (4)0.0089 (4)−0.0020 (4)
Geometric parameters (Å, º) top
O1A—C9A1.2878 (12)O1B—C9B1.2890 (12)
N1A—C7A1.3560 (13)N1B—C7B1.3533 (13)
N1A—N2A1.3628 (12)N1B—N2B1.3640 (12)
N1A—H1NA0.935 (16)N1B—H1NB0.913 (17)
N2A—C9A1.3655 (12)N2B—C9B1.3641 (12)
N2A—H2NA0.928 (19)N2B—H2NB0.933 (17)
C1A—C2A1.3875 (16)C1B—C2B1.3861 (16)
C1A—C6A1.4006 (14)C1B—C6B1.4004 (14)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.3878 (17)C2B—C3B1.3926 (17)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.3896 (16)C3B—C4B1.3901 (17)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.3893 (16)C4B—C5B1.3866 (16)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.3994 (14)C5B—C6B1.3979 (14)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.4708 (14)C6B—C7B1.4668 (14)
C7A—C8A1.3895 (13)C7B—C8B1.3920 (13)
C8A—C9A1.4233 (14)C8B—C9B1.4221 (14)
C8A—C10A1.4978 (13)C8B—C10B1.4946 (14)
C10A—H10A0.9600C10B—H10D0.9600
C10A—H10B0.9600C10B—H10E0.9600
C10A—H10C0.9600C10B—H10F0.9600
C7A—N1A—N2A108.49 (8)C7B—N1B—N2B108.33 (8)
C7A—N1A—H1NA129.6 (10)C7B—N1B—H1NB129.5 (11)
N2A—N1A—H1NA121.6 (10)N2B—N1B—H1NB120.7 (11)
N1A—N2A—C9A109.34 (8)N1B—N2B—C9B109.45 (9)
N1A—N2A—H2NA123.7 (11)N1B—N2B—H2NB123.4 (10)
C9A—N2A—H2NA125.5 (11)C9B—N2B—H2NB127.0 (10)
C2A—C1A—C6A120.42 (10)C2B—C1B—C6B120.09 (10)
C2A—C1A—H1AA119.8C2B—C1B—H1BA120.0
C6A—C1A—H1AA119.8C6B—C1B—H1BA120.0
C1A—C2A—C3A120.42 (10)C1B—C2B—C3B120.25 (10)
C1A—C2A—H2AA119.8C1B—C2B—H2BA119.9
C3A—C2A—H2AA119.8C3B—C2B—H2BA119.9
C2A—C3A—C4A119.66 (11)C4B—C3B—C2B119.85 (11)
C2A—C3A—H3AA120.2C4B—C3B—H3BA120.1
C4A—C3A—H3AA120.2C2B—C3B—H3BA120.1
C5A—C4A—C3A120.25 (10)C5B—C4B—C3B120.20 (10)
C5A—C4A—H4AA119.9C5B—C4B—H4BA119.9
C3A—C4A—H4AA119.9C3B—C4B—H4BA119.9
C4A—C5A—C6A120.49 (10)C4B—C5B—C6B120.22 (10)
C4A—C5A—H5AA119.8C4B—C5B—H5BA119.9
C6A—C5A—H5AA119.8C6B—C5B—H5BA119.9
C5A—C6A—C1A118.74 (10)C5B—C6B—C1B119.37 (10)
C5A—C6A—C7A120.29 (9)C5B—C6B—C7B120.73 (9)
C1A—C6A—C7A120.89 (9)C1B—C6B—C7B119.89 (9)
N1A—C7A—C8A109.11 (9)N1B—C7B—C8B109.25 (9)
N1A—C7A—C6A120.23 (9)N1B—C7B—C6B119.73 (9)
C8A—C7A—C6A130.60 (9)C8B—C7B—C6B130.99 (9)
C7A—C8A—C9A105.93 (8)C7B—C8B—C9B105.79 (8)
C7A—C8A—C10A129.40 (9)C7B—C8B—C10B128.55 (10)
C9A—C8A—C10A124.56 (9)C9B—C8B—C10B125.63 (9)
O1A—C9A—N2A122.59 (9)O1B—C9B—N2B121.99 (9)
O1A—C9A—C8A130.31 (9)O1B—C9B—C8B130.90 (9)
N2A—C9A—C8A107.10 (9)N2B—C9B—C8B107.09 (9)
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—C9A−1.33 (11)C7B—N1B—N2B—C9B−2.31 (11)
C6A—C1A—C2A—C3A0.33 (18)C6B—C1B—C2B—C3B−0.54 (17)
C1A—C2A—C3A—C4A0.55 (19)C1B—C2B—C3B—C4B0.32 (18)
C2A—C3A—C4A—C5A−0.48 (18)C2B—C3B—C4B—C5B0.73 (17)
C3A—C4A—C5A—C6A−0.47 (17)C3B—C4B—C5B—C6B−1.54 (16)
C4A—C5A—C6A—C1A1.33 (16)C4B—C5B—C6B—C1B1.30 (15)
C4A—C5A—C6A—C7A−175.25 (10)C4B—C5B—C6B—C7B−177.31 (9)
C2A—C1A—C6A—C5A−1.26 (16)C2B—C1B—C6B—C5B−0.27 (15)
C2A—C1A—C6A—C7A175.29 (10)C2B—C1B—C6B—C7B178.36 (10)
N2A—N1A—C7A—C8A1.22 (11)N2B—N1B—C7B—C8B0.43 (11)
N2A—N1A—C7A—C6A−176.28 (8)N2B—N1B—C7B—C6B178.45 (8)
C5A—C6A—C7A—N1A141.18 (10)C5B—C6B—C7B—N1B139.78 (10)
C1A—C6A—C7A—N1A−35.32 (14)C1B—C6B—C7B—N1B−38.83 (14)
C5A—C6A—C7A—C8A−35.71 (16)C5B—C6B—C7B—C8B−42.70 (16)
C1A—C6A—C7A—C8A147.80 (11)C1B—C6B—C7B—C8B138.69 (11)
N1A—C7A—C8A—C9A−0.64 (11)N1B—C7B—C8B—C9B1.50 (11)
C6A—C7A—C8A—C9A176.51 (10)C6B—C7B—C8B—C9B−176.23 (10)
N1A—C7A—C8A—C10A175.59 (10)N1B—C7B—C8B—C10B−176.60 (10)
C6A—C7A—C8A—C10A−7.25 (18)C6B—C7B—C8B—C10B5.67 (18)
N1A—N2A—C9A—O1A−178.72 (9)N1B—N2B—C9B—O1B−175.40 (9)
N1A—N2A—C9A—C8A0.91 (11)N1B—N2B—C9B—C8B3.21 (11)
C7A—C8A—C9A—O1A179.42 (10)C7B—C8B—C9B—O1B175.58 (10)
C10A—C8A—C9A—O1A2.96 (17)C10B—C8B—C9B—O1B−6.24 (17)
C7A—C8A—C9A—N2A−0.17 (11)C7B—C8B—C9B—N2B−2.85 (11)
C10A—C8A—C9A—N2A−176.63 (9)C10B—C8B—C9B—N2B175.32 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H1NB···O1Ai0.913 (17)1.796 (17)2.7001 (11)170.0 (16)
N1A—H1NA···O1B0.935 (19)1.78 (2)2.6987 (14)165.9 (16)
N2A—H2NA···O1Aii0.93 (2)1.768 (19)2.6917 (12)173.9 (17)
N2B—H2NB···O1Biii0.934 (18)1.752 (18)2.6850 (13)177.0 (16)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, −y+1/2, −z; (iii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formulaC10H10N2O
Mr174.20
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)25.9337 (4), 10.8100 (1), 14.1426 (2)
β (°) 118.961 (1)
V (Å3)3468.98 (8)
Z16
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.45 × 0.39 × 0.25
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.961, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections		36992, 5087, 4389
Rint0.036
(sin θ/λ)max (Å−1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.119, 1.03
No. of reflections5087
No. of parameters253
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.45, −0.22

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H1NB···O1Ai0.913 (17)1.796 (17)2.7001 (11)170.0 (16)
N1A—H1NA···O1B0.935 (19)1.78 (2)2.6987 (14)165.9 (16)
N2A—H2NA···O1Aii0.93 (2)1.768 (19)2.6917 (12)173.9 (17)
N2B—H2NB···O1Biii0.934 (18)1.752 (18)2.6850 (13)177.0 (16)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, −y+1/2, −z; (iii) −x+1, y, −z+1/2.
 

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian government and USM for the award of a Research Fellowship. VV is grateful to the DST–India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Pages o151-o152
https://doi.org/10.1107/S160053681005213X
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