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

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ISSN: 2056-9890

Ethyl 1,5-di­phenyl-1H-pyrazole-4-carboxyl­ate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, Manipal Institute of Technology, Manipal 576 104, India, cOrganic Chemistry Division, Department of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India, and dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India
*Correspondence e-mail: hkfun@usm.my

(Received 30 July 2010; accepted 4 August 2010; online 11 August 2010)

The asymmetric unit of the title compound, C18H16N2O2, contains two independent mol­ecules (A and B). In mol­ecule A, the pyrazole ring is inclined at angles of 48.86 (6) and 60.80 (6)° with respect to the two phenyl rings; the corresponding angles for mol­ecule B are 46.86 (6) and 58.63 (6)°. In the crystal, mol­ecules of type A are linked into sheets parallel to (001) via weak C—H⋯O hydrogen bonds, whereas the mol­ecules of type B are linked into chains along [010] via weak C—H⋯O hydrogen bonds.

Related literature

For general background to and the biological activity of pyrazole derivatives, see: Isloor et al. (2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.]); Lambert & Fowler (2005[Lambert, D. M. & Fowler, C. J. (2005). J. Med. Chem. 48, 5059-5087.]); Lan et al. (1999[Lan, R., Liu, Q., Fan, P., Lin, S., Fernando, S. R., McCallion, D. Pertwee, R. & Makriyannis, A. (1999). J. Med. Chem. 42, 769-776.]). For related structures, see: Fun et al. (2009[Fun, H.-K., Quah, C. K., Sarveswari, S., Vijayakumar, V. & Prasath, R. (2009). Acta Cryst. E65, o2707-o2708.]; 2010[Fun, H.-K., Goh, J. H., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2010). Acta Cryst. E66, o1828-o1829.]). 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.]). For standard 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 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.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16N2O2

  • Mr = 292.33

  • Triclinic, [P \overline 1]

  • a = 9.2015 (8) Å

  • b = 10.4638 (9) Å

  • c = 16.9332 (15) Å

  • α = 97.515 (2)°

  • β = 104.605 (2)°

  • γ = 104.578 (2)°

  • V = 1493.7 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.24 × 0.23 × 0.21 mm

Data collection
  • Bruker SMART APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.983

  • 35429 measured reflections

  • 10300 independent reflections

  • 7846 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.128

  • S = 1.03

  • 10300 reflections

  • 399 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3A—H3AA⋯O2Ai 0.93 2.43 3.3591 (16) 177
C3B—H3BA⋯O2Bi 0.93 2.46 3.3829 (16) 172
C13A—H13A⋯O2Aii 0.93 2.59 3.2622 (17) 129
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.

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


Comment top

Pyrazole and its derivatives represent one of the most active classes of compounds possessing a wide spectrum of biological activities. During the past years, considerable evidences have been accumulated to demonstrate the efficacy of pyrazole derivatives including antibacterial (Isloor et al., 2009), antifungal (Lambert & Fowler, 2005), herbicidal (Lan et al., 1999), insecticidal and other biological activities. In view of the potential importance of pyrazole derivatives, we have synthesized the title compound and its crystal structure is presented herein.

The title compound (Fig. 1) contains two indpendent molecules (A and B) in the asymmetric unit, with similar geometries. Each molecule consists of two phenyl rings and an ethyl carboxylate moiety attached to the pyrazole ring. In molecule A, the pyrazole ring (N1A/N2A/C7A-C9A) is inclined at angles of 48.86 (6) and 60.80 (6)° with respect to the C1A-C6A and C10A-C15A phenyl rings, respectively. The correspondening angles for molecule B are 46.86 (6) and 58.63 (6)°. Bond lengths and angles are within normal ranges, and comparable to closely related structures (Fun et al., 2009; 2010).

In the crystal packing (Fig. 2), molecules of type A are linked into sheets (Fig. 3) parallel to (001) via C3A–H3AA···O2Ai and C13A–H13A···O2Aii hydrogen bonds whereas the molecules B are linked into one-dimensional chains along [010] via a C3B–H3BA···O2Bi hydrogen bonds.

Related literature top

For general background to and the biological activity of pyrazole derivatives, see: Isloor et al. (2009); Lambert & Fowler (2005); Lan et al. (1999). For related structures, see: Fun et al. (2009; 2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of ethyl-3-(dimethylamino)-2-(phenylcarbonyl)prop-2-enoate (2.0 g, 0.0080 mol) and phenyl hydrazine (0.95 g, 0.0088 mol) in absolute ethanol (20 ml) was refluxed for 2 h. Reaction completion was monitored through thin layer chromatography and the reaction mixture was evaporated under reduced pressure. The residue was stirred with 1.5N HCl and the solid separated was filtered and dried under vacuum. The solid obtained was purified by column chromatography using silica gel 60-120 mesh size and petroleum ether: ethyl acetate as eluent to afford title compound as colourless crystals (2.0g, 86.9 %); melting point: 400-405 K.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.97 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups.

Structure description top

Pyrazole and its derivatives represent one of the most active classes of compounds possessing a wide spectrum of biological activities. During the past years, considerable evidences have been accumulated to demonstrate the efficacy of pyrazole derivatives including antibacterial (Isloor et al., 2009), antifungal (Lambert & Fowler, 2005), herbicidal (Lan et al., 1999), insecticidal and other biological activities. In view of the potential importance of pyrazole derivatives, we have synthesized the title compound and its crystal structure is presented herein.

The title compound (Fig. 1) contains two indpendent molecules (A and B) in the asymmetric unit, with similar geometries. Each molecule consists of two phenyl rings and an ethyl carboxylate moiety attached to the pyrazole ring. In molecule A, the pyrazole ring (N1A/N2A/C7A-C9A) is inclined at angles of 48.86 (6) and 60.80 (6)° with respect to the C1A-C6A and C10A-C15A phenyl rings, respectively. The correspondening angles for molecule B are 46.86 (6) and 58.63 (6)°. Bond lengths and angles are within normal ranges, and comparable to closely related structures (Fun et al., 2009; 2010).

In the crystal packing (Fig. 2), molecules of type A are linked into sheets (Fig. 3) parallel to (001) via C3A–H3AA···O2Ai and C13A–H13A···O2Aii hydrogen bonds whereas the molecules B are linked into one-dimensional chains along [010] via a C3B–H3BA···O2Bi hydrogen bonds.

For general background to and the biological activity of pyrazole derivatives, see: Isloor et al. (2009); Lambert & Fowler (2005); Lan et al. (1999). For related structures, see: Fun et al. (2009; 2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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 for non-H atoms and the atom-numbering scheme.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound, viewed approximately along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
[Figure 3] Fig. 3. The crystal packing of molecules of type A, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
Ethyl 1,5-diphenyl-1H-pyrazole-4-carboxylate top
Crystal data top
C18H16N2O2Z = 4
Mr = 292.33F(000) = 616
Triclinic, P1Dx = 1.300 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2015 (8) ÅCell parameters from 9846 reflections
b = 10.4638 (9) Åθ = 2.5–31.9°
c = 16.9332 (15) ŵ = 0.09 mm1
α = 97.515 (2)°T = 100 K
β = 104.605 (2)°Block, colourless
γ = 104.578 (2)°0.24 × 0.23 × 0.21 mm
V = 1493.7 (2) Å3
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
10300 independent reflections
Radiation source: fine-focus sealed tube7846 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 32.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1313
Tmin = 0.980, Tmax = 0.983k = 1515
35429 measured reflectionsl = 2525
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.3537P]
where P = (Fo2 + 2Fc2)/3
10300 reflections(Δ/σ)max = 0.001
399 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C18H16N2O2γ = 104.578 (2)°
Mr = 292.33V = 1493.7 (2) Å3
Triclinic, P1Z = 4
a = 9.2015 (8) ÅMo Kα radiation
b = 10.4638 (9) ŵ = 0.09 mm1
c = 16.9332 (15) ÅT = 100 K
α = 97.515 (2)°0.24 × 0.23 × 0.21 mm
β = 104.605 (2)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
10300 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
7846 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.983Rint = 0.044
35429 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.03Δρmax = 0.43 e Å3
10300 reflectionsΔρmin = 0.28 e Å3
399 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1A0.35565 (9)0.55673 (8)0.40840 (5)0.02192 (16)
O2A0.10538 (10)0.56385 (8)0.36818 (6)0.02587 (18)
N1A0.45702 (10)0.94866 (9)0.36135 (5)0.01681 (16)
N2A0.30699 (11)0.95931 (9)0.34270 (6)0.01975 (17)
C1A0.59279 (14)1.18876 (11)0.40504 (7)0.0206 (2)
H1AA0.52141.19830.43400.025*
C2A0.71181 (15)1.30011 (11)0.40425 (7)0.0244 (2)
H2AA0.71951.38510.43250.029*
C3A0.81991 (14)1.28608 (12)0.36156 (7)0.0241 (2)
H3AA0.90001.36110.36190.029*
C4A0.80757 (13)1.15950 (12)0.31842 (7)0.0236 (2)
H4AA0.87941.14990.28970.028*
C5A0.68803 (13)1.04687 (11)0.31798 (7)0.0205 (2)
H5AA0.67900.96210.28880.025*
C6A0.58225 (12)1.06269 (10)0.36174 (6)0.01680 (18)
C7A0.21906 (13)0.83992 (11)0.34605 (7)0.01922 (19)
H7AA0.11060.81700.33600.023*
C8A0.30951 (12)0.75140 (10)0.36682 (6)0.01709 (18)
C9A0.46399 (12)0.82515 (10)0.37630 (6)0.01586 (18)
C10A0.61394 (12)0.79251 (10)0.39942 (6)0.01714 (18)
C11A0.73369 (13)0.86837 (11)0.47083 (7)0.0213 (2)
H11A0.71820.93830.50440.026*
C12A0.87630 (14)0.83944 (13)0.49183 (8)0.0270 (2)
H12A0.95540.88920.54000.032*
C13A0.90112 (15)0.73682 (14)0.44132 (8)0.0299 (3)
H13A0.99710.71850.45530.036*
C14A0.78255 (16)0.66135 (13)0.36982 (8)0.0287 (3)
H14A0.79960.59290.33570.034*
C15A0.63871 (14)0.68781 (11)0.34916 (7)0.0223 (2)
H15A0.55880.63590.30190.027*
C16A0.24476 (12)0.61555 (10)0.38013 (6)0.01793 (19)
C17A0.29923 (14)0.41764 (11)0.41795 (7)0.0229 (2)
H17A0.20710.40690.43740.027*
H17B0.38010.39790.45940.027*
C18A0.25821 (16)0.32054 (13)0.33655 (8)0.0295 (3)
H18A0.23550.22980.34560.044*
H18B0.34530.33870.31390.044*
H18C0.16760.33090.29810.044*
O1B0.03838 (10)0.61507 (8)0.09374 (5)0.02177 (16)
O2B0.23012 (11)0.65343 (9)0.14598 (6)0.0317 (2)
N1B0.11226 (10)1.04064 (9)0.13619 (5)0.01698 (16)
N2B0.01563 (11)1.06169 (9)0.15725 (6)0.02083 (18)
C1B0.18999 (13)1.25412 (11)0.09434 (7)0.0210 (2)
H1BA0.08491.24240.06680.025*
C2B0.30546 (15)1.37023 (12)0.09588 (8)0.0253 (2)
H2BA0.27721.43700.06980.030*
C3B0.46273 (14)1.38736 (12)0.13605 (7)0.0248 (2)
H3BA0.53961.46510.13690.030*
C4B0.50423 (13)1.28742 (12)0.17498 (7)0.0234 (2)
H4BA0.60951.29800.20130.028*
C5B0.38976 (13)1.17171 (11)0.17499 (7)0.0202 (2)
H5BA0.41781.10560.20190.024*
C6B0.23336 (12)1.15597 (10)0.13444 (6)0.01708 (18)
C7B0.10204 (13)0.93979 (11)0.15709 (7)0.0208 (2)
H7BA0.19700.92250.16960.025*
C8B0.03368 (12)0.83895 (10)0.13579 (6)0.01782 (19)
C9B0.10638 (12)0.90767 (10)0.12275 (6)0.01598 (18)
C10B0.22948 (12)0.86100 (10)0.09737 (6)0.01613 (18)
C11B0.26595 (13)0.89043 (11)0.02510 (7)0.0201 (2)
H11B0.21100.93790.00750.024*
C12B0.38418 (14)0.84894 (12)0.00174 (7)0.0251 (2)
H12B0.40640.86710.04700.030*
C13B0.46887 (14)0.78059 (12)0.05093 (8)0.0268 (2)
H13B0.54920.75440.03580.032*
C14B0.43344 (14)0.75128 (12)0.12286 (8)0.0245 (2)
H14B0.49030.70550.15590.029*
C15B0.31331 (13)0.79004 (11)0.14585 (7)0.0199 (2)
H15B0.28890.76870.19350.024*
C16B0.11071 (13)0.69496 (11)0.12682 (7)0.0197 (2)
C17B0.10723 (15)0.47049 (11)0.08556 (7)0.0235 (2)
H17C0.07730.42120.04280.028*
H17E0.22100.44860.06830.028*
C18B0.05319 (17)0.42793 (13)0.16657 (8)0.0311 (3)
H18G0.09180.33150.15830.047*
H18D0.09280.46900.20730.047*
H18E0.05970.45600.18590.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0188 (4)0.0176 (3)0.0286 (4)0.0037 (3)0.0057 (3)0.0084 (3)
O2A0.0173 (4)0.0204 (4)0.0391 (5)0.0021 (3)0.0108 (3)0.0055 (3)
N1A0.0150 (4)0.0155 (4)0.0214 (4)0.0049 (3)0.0070 (3)0.0050 (3)
N2A0.0159 (4)0.0206 (4)0.0254 (4)0.0074 (3)0.0081 (3)0.0060 (3)
C1A0.0236 (5)0.0179 (5)0.0218 (5)0.0057 (4)0.0093 (4)0.0046 (4)
C2A0.0277 (6)0.0175 (5)0.0249 (5)0.0028 (4)0.0074 (4)0.0025 (4)
C3A0.0209 (5)0.0214 (5)0.0268 (5)0.0005 (4)0.0055 (4)0.0085 (4)
C4A0.0188 (5)0.0248 (5)0.0293 (5)0.0050 (4)0.0107 (4)0.0092 (4)
C5A0.0197 (5)0.0193 (5)0.0242 (5)0.0056 (4)0.0092 (4)0.0055 (4)
C6A0.0166 (5)0.0155 (4)0.0182 (4)0.0042 (4)0.0047 (4)0.0054 (3)
C7A0.0155 (5)0.0208 (5)0.0225 (5)0.0056 (4)0.0072 (4)0.0049 (4)
C8A0.0159 (4)0.0163 (4)0.0190 (4)0.0040 (4)0.0059 (4)0.0036 (3)
C9A0.0160 (4)0.0149 (4)0.0170 (4)0.0045 (3)0.0056 (3)0.0033 (3)
C10A0.0162 (4)0.0170 (4)0.0206 (4)0.0056 (4)0.0072 (4)0.0072 (3)
C11A0.0188 (5)0.0211 (5)0.0235 (5)0.0046 (4)0.0059 (4)0.0067 (4)
C12A0.0166 (5)0.0333 (6)0.0309 (6)0.0055 (5)0.0047 (4)0.0148 (5)
C13A0.0202 (5)0.0411 (7)0.0404 (7)0.0161 (5)0.0152 (5)0.0234 (6)
C14A0.0319 (6)0.0323 (6)0.0357 (6)0.0201 (5)0.0199 (5)0.0140 (5)
C15A0.0230 (5)0.0224 (5)0.0244 (5)0.0093 (4)0.0095 (4)0.0051 (4)
C16A0.0174 (5)0.0169 (4)0.0189 (4)0.0038 (4)0.0063 (4)0.0026 (3)
C17A0.0258 (6)0.0164 (5)0.0259 (5)0.0041 (4)0.0070 (4)0.0078 (4)
C18A0.0352 (7)0.0243 (6)0.0296 (6)0.0108 (5)0.0096 (5)0.0034 (4)
O1B0.0222 (4)0.0157 (3)0.0279 (4)0.0037 (3)0.0112 (3)0.0026 (3)
O2B0.0239 (4)0.0226 (4)0.0545 (6)0.0052 (3)0.0226 (4)0.0100 (4)
N1B0.0144 (4)0.0150 (4)0.0222 (4)0.0043 (3)0.0071 (3)0.0031 (3)
N2B0.0163 (4)0.0199 (4)0.0289 (5)0.0067 (3)0.0101 (4)0.0041 (3)
C1B0.0177 (5)0.0192 (5)0.0256 (5)0.0055 (4)0.0050 (4)0.0049 (4)
C2B0.0264 (6)0.0192 (5)0.0312 (6)0.0053 (4)0.0096 (5)0.0088 (4)
C3B0.0229 (5)0.0205 (5)0.0293 (5)0.0005 (4)0.0120 (4)0.0023 (4)
C4B0.0157 (5)0.0252 (5)0.0259 (5)0.0027 (4)0.0063 (4)0.0003 (4)
C5B0.0172 (5)0.0203 (5)0.0220 (5)0.0053 (4)0.0045 (4)0.0033 (4)
C6B0.0157 (4)0.0148 (4)0.0197 (4)0.0026 (3)0.0064 (4)0.0014 (3)
C7B0.0176 (5)0.0202 (5)0.0259 (5)0.0056 (4)0.0094 (4)0.0033 (4)
C8B0.0160 (5)0.0162 (4)0.0217 (5)0.0040 (4)0.0071 (4)0.0037 (3)
C9B0.0156 (4)0.0152 (4)0.0171 (4)0.0050 (3)0.0045 (3)0.0030 (3)
C10B0.0140 (4)0.0140 (4)0.0194 (4)0.0029 (3)0.0058 (3)0.0012 (3)
C11B0.0202 (5)0.0190 (5)0.0210 (5)0.0043 (4)0.0078 (4)0.0035 (4)
C12B0.0239 (5)0.0238 (5)0.0267 (5)0.0017 (4)0.0142 (4)0.0002 (4)
C13B0.0179 (5)0.0253 (5)0.0347 (6)0.0045 (4)0.0110 (4)0.0052 (4)
C14B0.0196 (5)0.0240 (5)0.0290 (6)0.0102 (4)0.0042 (4)0.0005 (4)
C15B0.0195 (5)0.0196 (5)0.0213 (5)0.0071 (4)0.0062 (4)0.0034 (4)
C16B0.0168 (5)0.0181 (5)0.0247 (5)0.0045 (4)0.0075 (4)0.0046 (4)
C17B0.0270 (6)0.0147 (4)0.0274 (5)0.0030 (4)0.0095 (4)0.0028 (4)
C18B0.0393 (7)0.0271 (6)0.0311 (6)0.0134 (5)0.0127 (5)0.0093 (5)
Geometric parameters (Å, º) top
O1A—C16A1.3402 (13)O1B—C16B1.3420 (13)
O1A—C17A1.4620 (13)O1B—C17B1.4587 (13)
O2A—C16A1.2123 (13)O2B—C16B1.2156 (13)
N1A—C9A1.3630 (13)N1B—C9B1.3651 (13)
N1A—N2A1.3728 (12)N1B—N2B1.3719 (12)
N1A—C6A1.4330 (13)N1B—C6B1.4311 (13)
N2A—C7A1.3235 (14)N2B—C7B1.3216 (14)
C1A—C2A1.3879 (15)C1B—C6B1.3882 (15)
C1A—C6A1.3906 (14)C1B—C2B1.3905 (16)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.3935 (17)C2B—C3B1.3893 (18)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.3893 (17)C3B—C4B1.3887 (18)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.3927 (15)C4B—C5B1.3905 (15)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.3917 (14)C5B—C6B1.3865 (15)
C5A—H5AA0.9300C5B—H5BA0.9300
C7A—C8A1.4142 (15)C7B—C8B1.4100 (14)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.3936 (14)C8B—C9B1.3947 (14)
C8A—C16A1.4668 (14)C8B—C16B1.4643 (14)
C9A—C10A1.4743 (15)C9B—C10B1.4749 (14)
C10A—C11A1.3940 (15)C10B—C15B1.3959 (15)
C10A—C15A1.3986 (14)C10B—C11B1.3996 (14)
C11A—C12A1.3903 (16)C11B—C12B1.3922 (15)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.3851 (19)C12B—C13B1.3862 (19)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.389 (2)C13B—C14B1.3898 (18)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.3882 (17)C14B—C15B1.3926 (15)
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9300C15B—H15B0.9300
C17A—C18A1.5010 (16)C17B—C18B1.5015 (17)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17E0.9700
C18A—H18A0.9600C18B—H18G0.9600
C18A—H18B0.9600C18B—H18D0.9600
C18A—H18C0.9600C18B—H18E0.9600
C16A—O1A—C17A116.10 (9)C16B—O1B—C17B115.69 (8)
C9A—N1A—N2A112.87 (8)C9B—N1B—N2B112.76 (8)
C9A—N1A—C6A128.77 (9)C9B—N1B—C6B129.09 (9)
N2A—N1A—C6A118.36 (8)N2B—N1B—C6B118.10 (8)
C7A—N2A—N1A104.39 (9)C7B—N2B—N1B104.38 (8)
C2A—C1A—C6A118.80 (10)C6B—C1B—C2B119.22 (10)
C2A—C1A—H1AA120.6C6B—C1B—H1BA120.4
C6A—C1A—H1AA120.6C2B—C1B—H1BA120.4
C1A—C2A—C3A120.78 (10)C3B—C2B—C1B120.56 (11)
C1A—C2A—H2AA119.6C3B—C2B—H2BA119.7
C3A—C2A—H2AA119.6C1B—C2B—H2BA119.7
C4A—C3A—C2A119.73 (10)C4B—C3B—C2B119.46 (11)
C4A—C3A—H3AA120.1C4B—C3B—H3BA120.3
C2A—C3A—H3AA120.1C2B—C3B—H3BA120.3
C3A—C4A—C5A120.24 (10)C3B—C4B—C5B120.59 (11)
C3A—C4A—H4AA119.9C3B—C4B—H4BA119.7
C5A—C4A—H4AA119.9C5B—C4B—H4BA119.7
C6A—C5A—C4A119.18 (10)C6B—C5B—C4B119.24 (10)
C6A—C5A—H5AA120.4C6B—C5B—H5BA120.4
C4A—C5A—H5AA120.4C4B—C5B—H5BA120.4
C1A—C6A—C5A121.27 (10)C5B—C6B—C1B120.92 (10)
C1A—C6A—N1A118.48 (9)C5B—C6B—N1B120.56 (9)
C5A—C6A—N1A120.24 (9)C1B—C6B—N1B118.47 (9)
N2A—C7A—C8A111.99 (9)N2B—C7B—C8B112.23 (9)
N2A—C7A—H7AA124.0N2B—C7B—H7BA123.9
C8A—C7A—H7AA124.0C8B—C7B—H7BA123.9
C9A—C8A—C7A105.26 (9)C9B—C8B—C7B105.21 (9)
C9A—C8A—C16A130.70 (10)C9B—C8B—C16B131.97 (9)
C7A—C8A—C16A123.90 (9)C7B—C8B—C16B122.74 (9)
N1A—C9A—C8A105.49 (9)N1B—C9B—C8B105.43 (9)
N1A—C9A—C10A122.05 (9)N1B—C9B—C10B122.19 (9)
C8A—C9A—C10A132.43 (9)C8B—C9B—C10B132.36 (9)
C11A—C10A—C15A119.52 (10)C15B—C10B—C11B119.26 (9)
C11A—C10A—C9A119.93 (9)C15B—C10B—C9B120.66 (9)
C15A—C10A—C9A120.52 (10)C11B—C10B—C9B120.06 (9)
C12A—C11A—C10A120.01 (11)C12B—C11B—C10B120.32 (11)
C12A—C11A—H11A120.0C12B—C11B—H11B119.8
C10A—C11A—H11A120.0C10B—C11B—H11B119.8
C13A—C12A—C11A120.29 (12)C13B—C12B—C11B120.14 (11)
C13A—C12A—H12A119.9C13B—C12B—H12B119.9
C11A—C12A—H12A119.9C11B—C12B—H12B119.9
C12A—C13A—C14A119.96 (11)C12B—C13B—C14B119.81 (10)
C12A—C13A—H13A120.0C12B—C13B—H13B120.1
C14A—C13A—H13A120.0C14B—C13B—H13B120.1
C15A—C14A—C13A120.17 (11)C13B—C14B—C15B120.44 (11)
C15A—C14A—H14A119.9C13B—C14B—H14B119.8
C13A—C14A—H14A119.9C15B—C14B—H14B119.8
C14A—C15A—C10A120.02 (11)C14B—C15B—C10B120.00 (10)
C14A—C15A—H15A120.0C14B—C15B—H15B120.0
C10A—C15A—H15A120.0C10B—C15B—H15B120.0
O2A—C16A—O1A123.97 (10)O2B—C16B—O1B124.08 (10)
O2A—C16A—C8A123.00 (10)O2B—C16B—C8B122.69 (10)
O1A—C16A—C8A113.02 (9)O1B—C16B—C8B113.22 (9)
O1A—C17A—C18A110.68 (9)O1B—C17B—C18B111.06 (10)
O1A—C17A—H17A109.5O1B—C17B—H17C109.4
C18A—C17A—H17A109.5C18B—C17B—H17C109.4
O1A—C17A—H17B109.5O1B—C17B—H17E109.4
C18A—C17A—H17B109.5C18B—C17B—H17E109.4
H17A—C17A—H17B108.1H17C—C17B—H17E108.0
C17A—C18A—H18A109.5C17B—C18B—H18G109.5
C17A—C18A—H18B109.5C17B—C18B—H18D109.5
H18A—C18A—H18B109.5H18G—C18B—H18D109.5
C17A—C18A—H18C109.5C17B—C18B—H18E109.5
H18A—C18A—H18C109.5H18G—C18B—H18E109.5
H18B—C18A—H18C109.5H18D—C18B—H18E109.5
C9A—N1A—N2A—C7A0.07 (11)C9B—N1B—N2B—C7B0.18 (12)
C6A—N1A—N2A—C7A179.13 (9)C6B—N1B—N2B—C7B177.38 (9)
C6A—C1A—C2A—C3A0.58 (17)C6B—C1B—C2B—C3B0.86 (17)
C1A—C2A—C3A—C4A0.76 (18)C1B—C2B—C3B—C4B0.09 (17)
C2A—C3A—C4A—C5A0.20 (18)C2B—C3B—C4B—C5B0.87 (17)
C3A—C4A—C5A—C6A0.50 (17)C3B—C4B—C5B—C6B1.04 (16)
C2A—C1A—C6A—C5A0.14 (16)C4B—C5B—C6B—C1B0.24 (15)
C2A—C1A—C6A—N1A178.67 (10)C4B—C5B—C6B—N1B177.47 (9)
C4A—C5A—C6A—C1A0.68 (16)C2B—C1B—C6B—C5B0.70 (16)
C4A—C5A—C6A—N1A179.18 (10)C2B—C1B—C6B—N1B176.58 (10)
C9A—N1A—C6A—C1A132.33 (11)C9B—N1B—C6B—C5B46.46 (15)
N2A—N1A—C6A—C1A48.61 (13)N2B—N1B—C6B—C5B130.65 (10)
C9A—N1A—C6A—C5A49.12 (15)C9B—N1B—C6B—C1B136.25 (11)
N2A—N1A—C6A—C5A129.93 (11)N2B—N1B—C6B—C1B46.64 (13)
N1A—N2A—C7A—C8A0.13 (11)N1B—N2B—C7B—C8B0.39 (12)
N2A—C7A—C8A—C9A0.14 (12)N2B—C7B—C8B—C9B0.45 (13)
N2A—C7A—C8A—C16A175.97 (9)N2B—C7B—C8B—C16B176.57 (10)
N2A—N1A—C9A—C8A0.01 (11)N2B—N1B—C9B—C8B0.09 (12)
C6A—N1A—C9A—C8A179.11 (9)C6B—N1B—C9B—C8B177.32 (10)
N2A—N1A—C9A—C10A178.57 (9)N2B—N1B—C9B—C10B178.45 (9)
C6A—N1A—C9A—C10A2.33 (15)C6B—N1B—C9B—C10B4.31 (16)
C7A—C8A—C9A—N1A0.09 (11)C7B—C8B—C9B—N1B0.30 (11)
C16A—C8A—C9A—N1A175.66 (10)C16B—C8B—C9B—N1B176.32 (11)
C7A—C8A—C9A—C10A178.43 (10)C7B—C8B—C9B—C10B178.43 (11)
C16A—C8A—C9A—C10A2.68 (19)C16B—C8B—C9B—C10B1.8 (2)
N1A—C9A—C10A—C11A59.02 (14)N1B—C9B—C10B—C15B121.72 (11)
C8A—C9A—C10A—C11A119.10 (13)C8B—C9B—C10B—C15B60.41 (16)
N1A—C9A—C10A—C15A119.47 (11)N1B—C9B—C10B—C11B56.76 (14)
C8A—C9A—C10A—C15A62.42 (15)C8B—C9B—C10B—C11B121.11 (13)
C15A—C10A—C11A—C12A0.23 (16)C15B—C10B—C11B—C12B0.22 (16)
C9A—C10A—C11A—C12A178.73 (10)C9B—C10B—C11B—C12B178.72 (10)
C10A—C11A—C12A—C13A1.08 (17)C10B—C11B—C12B—C13B1.36 (17)
C11A—C12A—C13A—C14A0.71 (18)C11B—C12B—C13B—C14B1.23 (17)
C12A—C13A—C14A—C15A0.50 (18)C12B—C13B—C14B—C15B0.04 (17)
C13A—C14A—C15A—C10A1.35 (18)C13B—C14B—C15B—C10B1.18 (17)
C11A—C10A—C15A—C14A0.98 (16)C11B—C10B—C15B—C14B1.04 (16)
C9A—C10A—C15A—C14A177.51 (10)C9B—C10B—C15B—C14B177.45 (10)
C17A—O1A—C16A—O2A5.26 (15)C17B—O1B—C16B—O2B3.28 (16)
C17A—O1A—C16A—C8A176.13 (8)C17B—O1B—C16B—C8B178.27 (9)
C9A—C8A—C16A—O2A179.16 (11)C9B—C8B—C16B—O2B175.52 (12)
C7A—C8A—C16A—O2A5.79 (16)C7B—C8B—C16B—O2B8.35 (18)
C9A—C8A—C16A—O1A2.22 (15)C9B—C8B—C16B—O1B6.00 (17)
C7A—C8A—C16A—O1A172.83 (9)C7B—C8B—C16B—O1B170.12 (10)
C16A—O1A—C17A—C18A83.99 (12)C16B—O1B—C17B—C18B81.78 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3AA···O2Ai0.932.433.3591 (16)177
C3B—H3BA···O2Bi0.932.463.3829 (16)172
C13A—H13A···O2Aii0.932.593.2622 (17)129
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC18H16N2O2
Mr292.33
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.2015 (8), 10.4638 (9), 16.9332 (15)
α, β, γ (°)97.515 (2), 104.605 (2), 104.578 (2)
V3)1493.7 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.24 × 0.23 × 0.21
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.980, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
35429, 10300, 7846
Rint0.044
(sin θ/λ)max1)0.747
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.128, 1.03
No. of reflections10300
No. of parameters399
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.28

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
C3A—H3AA···O2Ai0.932.433.3591 (16)177
C3B—H3BA···O2Bi0.932.463.3829 (16)172
C13A—H13A···O2Aii0.932.593.2622 (17)129
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). CKQ also thanks USM for the award of a USM fellowship. AMI is thankful to the Director of the National Institute of Technology–Karnataka, Surathkal, India, for providing research facilities and encouragement.

References

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