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ISSN: 2056-9890

(E)-1-(1-Benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-3-phenyl­prop-2-en-1-one

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai-625 021, Tamil Nadu, India, and cDepartment of Chemistry, Thanthai Hans Roever College, Perambalur-621 212, Tamil Nadu, India
*Correspondence e-mail: hkfun@usm.my

(Received 12 September 2011; accepted 16 September 2011; online 30 September 2011)

The asymmetric unit of the title compound, C19H17N3O, contains two independent mol­ecules. In one mol­ecule, the essentially planar triazole ring [maximum deviation = 0.003 (2) Å] forms dihedral angles of 5.57 (12) and 87.51 (12)° with the two phenyl rings, while in the other mol­ecule [maximum deviation in triazole ring = 0.001 (2) Å] these angles are 1.55 (10) and 82.73 (11)°. The dihedral angles between the two phenyl rings in the two mol­ecules are 87.77 (13) and 81.22 (11)°. In the crystal, the independent mol­ecules are connected via a weak C—H⋯N hydrogen bond, forming dimers. Further stabilization is provided by weak C—H⋯π inter­actions.

Related literature

For applications of 1,2,3-triazole compounds, see: Banerjee et al. (1996)[Banerjee, A., Nayak, P. L. & Rout, M. K. (1996). J. Indian Chem. Soc. 43, 578-82.]; Laliberte et al. (1967[Laliberte, R., Campbell, D. J. & Bruderlein, F. (1967). Can. J. Pharm. Sci. 2, 37-43.]); Suwa et al. (1984[Suwa, T., Fukushima, K. & Kyogoku, K. (1984). Jpn J. Pharm. 34, 89-94.]). For applications of chalcones, see: Ballesteros et al. (1995[Ballesteros, J. F., Sanz, M. J., Ubeda, A., Miranda, M. A., Iborra, S., Paya, M. & Alcaraz, M. J. (1995). J. Med. Chem. 38, 2794-2797.]); Kothari et al. (1999[Kothari, S., Vyas, R. & Verma, B. L. (1999). Indian J. Heteroat. Chem. 8, 285-288.]); Nagaraj & Reddy (2007[Nagaraj, A. & Reddy, C. S. J. (2007). Heteroat. Chem. 44, 1181-1185.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17N3O

  • Mr = 303.36

  • Monoclinic, P 21 /c

  • a = 12.3117 (14) Å

  • b = 13.8016 (15) Å

  • c = 19.312 (2) Å

  • β = 99.665 (2)°

  • V = 3235.0 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.46 × 0.33 × 0.11 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, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.991

  • 32508 measured reflections

  • 9403 independent reflections

  • 4890 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.219

  • S = 1.03

  • 9403 reflections

  • 417 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C14A–C19A and C14B–C19B rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C13A—H13A⋯N1Bi 0.97 2.50 3.453 (3) 166
C1B—H1BACg1ii 0.93 2.97 3.893 (3) 174
C13B—H13CCg2iii 0.97 2.61 3.528 (2) 159
Symmetry codes: (i) -x, -y+1, -z; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y+2, -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

Organic compounds, having the 1,2,3-triazole nucleus, may induce antiviral, agonist, antibacterial, antimicrobial, anti-HIV, anticonvulsants and anti-allergic properties. In addition, compounds having 1,2,3-triazole group have found industrial application as dyes, corrosion inhibitors, sensors and photo-stabilizers (Banerjee et al., 1996; Laliberte et al., 1967; Suwa et al., 1984). The chalcone skeleton is a unique template for synthesizing various heterocyclic compounds. The compounds with the backbone of chalcones were associated with different biological activities like cardiovascular, antispasmodic, anthelmintics, antiulcer, anti-inflammatory, antiviral, antiallergic, fungicidal, bactericidal, insecticidal, antitumor, herbicidal, anticancer, antitubercular and anti-HIV (Ballesteros et al., 1995; Kothari et al., 1999; Nagaraj & Reddy, 2007) properties. Chalcones, considered as the precursors of flavonoids and isoflavonoids, are abundant in edible plants, and have also been shown to display a diverse array of pharmacological activities. The presence of a reactive α, β-unsaturated keto function in chalcones is found to be responsible for their activities.

The asymmetric unit of the title compound, (I), contains two crystallographically independent (E)-1-(1-benzyl-5-methyl-1H- 1,2,3-triazol-4-yl)-3-phenylprop-2-en-1-one molecules (A & B) as shown in Fig. 1. The triazole (N1A–N3A/C10A/C11A):(N1B–N3B/C10B/C11B) units are essentially planar, with maximum deviations of 0.003 (2) Å for atom C10A and 0.001 (2) Å for atom C11B. In molecule A the essentially planar triazole ring forms dihedral angles of 5.57 (12) and 87.51 (12)° with the two phenyl rings while in molecule B these angles are 1.55 (10) and 82.73 (11)°. The dihedral angles between the two phenyl(C1A–C6A/C14A–C19A): (C1B–C6B/C14B–C19B) rings in the independent molecules are 87.77 (13)° and 81.22 (11)° respectively.

In the crystal, (Fig. 2), two independent molecules are connected via intermolecular C—H···N hydrogen bonds (Table 1), forming dimers. Furthermore, the crystal structure is stabilized by weak C—H···π interactions involving the Cg1 (C14A–C19A) and Cg1 (C14B–C19B) rings.

Related literature top

For applications of 1,2,3-triazole compounds, see: Banerjee et al. (1996); Laliberte et al. (1967); Suwa et al. (1984). For applications of chalcones, see: Ballesteros et al. (1995); Kothari et al. (1999); Nagaraj & Reddy (2007).

Experimental top

A mixture of 4-acetyl-1-benzyl-5-methyl-1,2,3-triazole (0.20g, 0.93mmol) and benzaldehyde (0.98 g, 0.93 mmol) was stirred in ethanol (2–3 ml) and then 50% sodium hydroxide solution (0.5 ml) was added to it. The mixture was stirred for 3 minutes at room temperature and poured onto excess of crushed ice and neutralized with dilute hydrochloric acid. 1-Benzyl-5-methyl-1,2,3-triazol-4-yl-3-phenylprop-2-en-1-one precipitated as solid, which were filtered and recrystallized from ethanol. Yield: 0.27g (97%). M.p. 157–158°C.

Refinement top

All hydrogen atoms were positioned geometrically [C–H = 0.93–0.97 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

Organic compounds, having the 1,2,3-triazole nucleus, may induce antiviral, agonist, antibacterial, antimicrobial, anti-HIV, anticonvulsants and anti-allergic properties. In addition, compounds having 1,2,3-triazole group have found industrial application as dyes, corrosion inhibitors, sensors and photo-stabilizers (Banerjee et al., 1996; Laliberte et al., 1967; Suwa et al., 1984). The chalcone skeleton is a unique template for synthesizing various heterocyclic compounds. The compounds with the backbone of chalcones were associated with different biological activities like cardiovascular, antispasmodic, anthelmintics, antiulcer, anti-inflammatory, antiviral, antiallergic, fungicidal, bactericidal, insecticidal, antitumor, herbicidal, anticancer, antitubercular and anti-HIV (Ballesteros et al., 1995; Kothari et al., 1999; Nagaraj & Reddy, 2007) properties. Chalcones, considered as the precursors of flavonoids and isoflavonoids, are abundant in edible plants, and have also been shown to display a diverse array of pharmacological activities. The presence of a reactive α, β-unsaturated keto function in chalcones is found to be responsible for their activities.

The asymmetric unit of the title compound, (I), contains two crystallographically independent (E)-1-(1-benzyl-5-methyl-1H- 1,2,3-triazol-4-yl)-3-phenylprop-2-en-1-one molecules (A & B) as shown in Fig. 1. The triazole (N1A–N3A/C10A/C11A):(N1B–N3B/C10B/C11B) units are essentially planar, with maximum deviations of 0.003 (2) Å for atom C10A and 0.001 (2) Å for atom C11B. In molecule A the essentially planar triazole ring forms dihedral angles of 5.57 (12) and 87.51 (12)° with the two phenyl rings while in molecule B these angles are 1.55 (10) and 82.73 (11)°. The dihedral angles between the two phenyl(C1A–C6A/C14A–C19A): (C1B–C6B/C14B–C19B) rings in the independent molecules are 87.77 (13)° and 81.22 (11)° respectively.

In the crystal, (Fig. 2), two independent molecules are connected via intermolecular C—H···N hydrogen bonds (Table 1), forming dimers. Furthermore, the crystal structure is stabilized by weak C—H···π interactions involving the Cg1 (C14A–C19A) and Cg1 (C14B–C19B) rings.

For applications of 1,2,3-triazole compounds, see: Banerjee et al. (1996); Laliberte et al. (1967); Suwa et al. (1984). For applications of chalcones, see: Ballesteros et al. (1995); Kothari et al. (1999); Nagaraj & Reddy (2007).

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 asymmetric unit of the title compound showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound (I). Hydrogen bonds are shown as dashed lines.
(E)-1-(1-Benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-3-phenylprop-2- en-1-one top
Crystal data top
C19H17N3OF(000) = 1280
Mr = 303.36Dx = 1.246 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5224 reflections
a = 12.3117 (14) Åθ = 2.2–22.7°
b = 13.8016 (15) ŵ = 0.08 mm1
c = 19.312 (2) ÅT = 296 K
β = 99.665 (2)°Block, colourless
V = 3235.0 (6) Å30.46 × 0.33 × 0.11 mm
Z = 8
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
9403 independent reflections
Radiation source: fine-focus sealed tube4890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 30.1°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1617
Tmin = 0.965, Tmax = 0.991k = 1919
32508 measured reflectionsl = 2723
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) = 0.219H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1167P)2]
where P = (Fo2 + 2Fc2)/3
9403 reflections(Δ/σ)max < 0.001
417 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C19H17N3OV = 3235.0 (6) Å3
Mr = 303.36Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.3117 (14) ŵ = 0.08 mm1
b = 13.8016 (15) ÅT = 296 K
c = 19.312 (2) Å0.46 × 0.33 × 0.11 mm
β = 99.665 (2)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
9403 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
4890 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.991Rint = 0.042
32508 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.219H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
9403 reflectionsΔρmin = 0.28 e Å3
417 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1A0.27709 (13)0.39668 (11)0.24684 (8)0.0715 (4)
N1A0.16032 (15)0.34511 (11)0.06825 (9)0.0608 (4)
N2A0.07387 (16)0.29373 (13)0.04346 (9)0.0685 (5)
N3A0.03211 (14)0.25962 (11)0.09973 (9)0.0565 (4)
C1A0.5850 (2)0.60875 (17)0.19015 (18)0.0902 (8)
H1AA0.59160.60290.23870.108*
C2A0.6648 (3)0.6594 (2)0.1605 (3)0.1247 (14)
H2AA0.72520.68590.18990.150*
C3A0.6558 (3)0.6705 (2)0.0899 (3)0.1209 (15)
H3AA0.70940.70420.07110.145*
C4A0.5677 (3)0.63209 (19)0.04714 (19)0.1042 (10)
H4AA0.56100.64000.00120.125*
C5A0.4883 (2)0.58161 (15)0.07423 (14)0.0766 (7)
H5AA0.42820.55650.04390.092*
C6A0.49611 (16)0.56747 (12)0.14621 (12)0.0584 (5)
C7A0.41637 (16)0.51129 (12)0.17720 (11)0.0545 (5)
H7AA0.42300.51420.22580.065*
C8A0.33539 (16)0.45646 (12)0.14430 (11)0.0532 (5)
H8AA0.32360.45390.09550.064*
C9A0.26372 (16)0.39958 (12)0.18261 (10)0.0505 (4)
C10A0.17414 (16)0.34519 (12)0.13959 (10)0.0488 (4)
C11A0.09202 (15)0.28976 (12)0.16033 (10)0.0490 (4)
C12A0.06483 (19)0.26389 (17)0.23003 (12)0.0702 (6)
H12A0.01340.26790.22830.105*
H12B0.10110.30800.26480.105*
H12C0.08920.19900.24200.105*
C13A0.06699 (17)0.20040 (14)0.08836 (13)0.0666 (6)
H13A0.10710.21340.04160.080*
H13B0.11360.21970.12180.080*
C14A0.04614 (16)0.09291 (13)0.09558 (10)0.0505 (4)
C15A0.13275 (19)0.03439 (16)0.10419 (13)0.0724 (6)
H15A0.20030.06200.10820.087*
C16A0.1209 (3)0.06517 (18)0.10692 (16)0.0901 (8)
H16A0.18030.10400.11290.108*
C17A0.0221 (3)0.10682 (16)0.10088 (13)0.0848 (8)
H17A0.01450.17390.10160.102*
C18A0.0648 (3)0.04917 (17)0.09374 (14)0.0834 (7)
H18A0.13270.07680.09090.100*
C19A0.0526 (2)0.05009 (16)0.09074 (14)0.0730 (6)
H19A0.11250.08870.08530.088*
O1B0.23447 (13)0.69469 (10)0.24399 (7)0.0659 (4)
N1B0.24505 (14)0.73675 (12)0.06272 (8)0.0584 (4)
N2B0.31548 (15)0.78740 (12)0.03440 (8)0.0624 (5)
N3B0.38931 (13)0.82428 (10)0.08821 (8)0.0492 (4)
C1B0.09734 (19)0.47430 (14)0.20382 (13)0.0669 (6)
H1BA0.07180.48040.25170.080*
C2B0.1901 (2)0.41806 (17)0.18030 (19)0.0877 (8)
H2BA0.22600.38680.21260.105*
C3B0.2287 (2)0.40848 (16)0.10989 (19)0.0883 (8)
H3BA0.29070.37080.09450.106*
C4B0.1757 (2)0.45471 (16)0.06215 (15)0.0787 (7)
H4BA0.20160.44820.01430.094*
C5B0.08397 (17)0.51079 (14)0.08503 (12)0.0616 (5)
H5BA0.04900.54220.05230.074*
C6B0.04284 (15)0.52120 (11)0.15621 (10)0.0489 (4)
C7B0.05448 (15)0.57853 (12)0.18235 (10)0.0488 (4)
H7BA0.07900.57640.23060.059*
C8B0.11238 (15)0.63355 (12)0.14558 (10)0.0496 (4)
H8BA0.09190.63710.09710.059*
C9B0.20855 (15)0.68918 (12)0.18018 (10)0.0483 (4)
C10B0.27209 (14)0.74073 (11)0.13362 (9)0.0442 (4)
C11B0.36537 (15)0.79731 (11)0.15077 (9)0.0431 (4)
C12B0.43183 (18)0.82731 (15)0.21835 (10)0.0625 (5)
H12D0.50820.83000.21370.094*
H12E0.42230.78130.25410.094*
H12F0.40810.89010.23120.094*
C13B0.47926 (17)0.88434 (13)0.07265 (11)0.0550 (5)
H13C0.48610.87570.02370.066*
H13D0.54750.86270.10110.066*
C14B0.46353 (15)0.99030 (12)0.08633 (9)0.0465 (4)
C15B0.36468 (17)1.03723 (14)0.06188 (12)0.0635 (5)
H15B0.30531.00230.03810.076*
C16B0.3540 (2)1.13550 (16)0.07273 (14)0.0780 (7)
H16B0.28751.16640.05670.094*
C17B0.4418 (2)1.18741 (16)0.10720 (13)0.0772 (7)
H17B0.43451.25350.11450.093*
C18B0.5396 (2)1.14258 (16)0.13074 (12)0.0731 (6)
H18B0.59911.17830.15350.088*
C19B0.55057 (17)1.04482 (14)0.12086 (10)0.0582 (5)
H19B0.61741.01470.13760.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0724 (10)0.0830 (10)0.0565 (9)0.0170 (8)0.0029 (7)0.0035 (7)
N1A0.0682 (11)0.0581 (9)0.0556 (10)0.0100 (8)0.0087 (8)0.0002 (7)
N2A0.0774 (13)0.0655 (10)0.0592 (10)0.0148 (9)0.0015 (9)0.0014 (8)
N3A0.0524 (9)0.0460 (8)0.0675 (11)0.0039 (7)0.0006 (8)0.0069 (7)
C1A0.0579 (14)0.0708 (14)0.134 (2)0.0107 (12)0.0069 (15)0.0123 (15)
C2A0.0603 (17)0.083 (2)0.224 (5)0.0254 (15)0.003 (2)0.006 (3)
C3A0.089 (2)0.0598 (15)0.230 (5)0.0055 (16)0.074 (3)0.008 (2)
C4A0.120 (3)0.0661 (14)0.142 (3)0.0103 (17)0.067 (2)0.0075 (16)
C5A0.0793 (16)0.0583 (12)0.0964 (19)0.0121 (12)0.0273 (14)0.0028 (12)
C6A0.0468 (10)0.0385 (8)0.0901 (16)0.0027 (8)0.0122 (10)0.0037 (9)
C7A0.0493 (10)0.0457 (9)0.0668 (12)0.0045 (8)0.0045 (9)0.0013 (8)
C8A0.0491 (10)0.0495 (9)0.0602 (12)0.0018 (8)0.0066 (9)0.0004 (8)
C9A0.0490 (10)0.0447 (9)0.0562 (12)0.0017 (8)0.0045 (9)0.0029 (8)
C10A0.0508 (10)0.0416 (8)0.0530 (11)0.0018 (8)0.0061 (8)0.0029 (7)
C11A0.0451 (10)0.0400 (8)0.0601 (11)0.0036 (7)0.0035 (8)0.0058 (8)
C12A0.0592 (13)0.0796 (14)0.0724 (14)0.0070 (11)0.0125 (11)0.0183 (11)
C13A0.0484 (11)0.0533 (10)0.0912 (16)0.0041 (9)0.0082 (11)0.0040 (10)
C14A0.0484 (10)0.0504 (9)0.0512 (10)0.0041 (8)0.0041 (8)0.0019 (8)
C15A0.0571 (13)0.0664 (13)0.0930 (17)0.0101 (11)0.0108 (12)0.0058 (11)
C16A0.091 (2)0.0645 (13)0.111 (2)0.0261 (14)0.0064 (16)0.0132 (13)
C17A0.126 (2)0.0488 (11)0.0778 (16)0.0010 (15)0.0108 (16)0.0007 (11)
C18A0.100 (2)0.0651 (13)0.0914 (18)0.0206 (14)0.0343 (15)0.0028 (12)
C19A0.0648 (14)0.0600 (11)0.0987 (18)0.0026 (11)0.0266 (13)0.0088 (11)
O1B0.0717 (10)0.0723 (9)0.0529 (9)0.0186 (7)0.0080 (7)0.0016 (7)
N1B0.0594 (10)0.0620 (9)0.0519 (10)0.0128 (8)0.0038 (8)0.0007 (7)
N2B0.0669 (11)0.0679 (10)0.0509 (10)0.0157 (9)0.0057 (8)0.0004 (8)
N3B0.0507 (9)0.0444 (7)0.0529 (9)0.0063 (7)0.0099 (7)0.0007 (6)
C1B0.0636 (13)0.0617 (11)0.0790 (15)0.0020 (10)0.0224 (11)0.0143 (10)
C2B0.0636 (15)0.0662 (14)0.140 (3)0.0110 (12)0.0360 (17)0.0278 (15)
C3B0.0551 (14)0.0569 (12)0.148 (3)0.0101 (11)0.0024 (16)0.0066 (15)
C4B0.0667 (15)0.0671 (13)0.0966 (18)0.0092 (12)0.0031 (13)0.0088 (12)
C5B0.0578 (12)0.0557 (10)0.0716 (14)0.0088 (10)0.0116 (10)0.0009 (9)
C6B0.0453 (9)0.0379 (8)0.0649 (12)0.0017 (7)0.0136 (9)0.0016 (8)
C7B0.0476 (10)0.0432 (8)0.0562 (10)0.0022 (8)0.0109 (8)0.0009 (8)
C8B0.0474 (10)0.0480 (9)0.0535 (11)0.0057 (8)0.0092 (8)0.0008 (8)
C9B0.0488 (10)0.0419 (8)0.0541 (11)0.0006 (8)0.0082 (8)0.0021 (7)
C10B0.0432 (9)0.0388 (8)0.0494 (10)0.0022 (7)0.0040 (8)0.0014 (7)
C11B0.0434 (9)0.0356 (7)0.0507 (10)0.0002 (7)0.0093 (8)0.0002 (7)
C12B0.0605 (12)0.0674 (11)0.0575 (12)0.0157 (10)0.0035 (10)0.0029 (9)
C13B0.0525 (11)0.0504 (9)0.0661 (12)0.0042 (8)0.0219 (9)0.0036 (8)
C14B0.0454 (10)0.0471 (9)0.0493 (10)0.0045 (8)0.0151 (8)0.0044 (7)
C15B0.0476 (11)0.0606 (11)0.0823 (15)0.0027 (9)0.0108 (10)0.0075 (10)
C16B0.0713 (15)0.0661 (13)0.1014 (19)0.0187 (12)0.0285 (14)0.0176 (13)
C17B0.101 (2)0.0516 (11)0.0844 (16)0.0004 (13)0.0319 (15)0.0062 (11)
C18B0.0851 (17)0.0654 (13)0.0688 (14)0.0132 (13)0.0127 (13)0.0163 (11)
C19B0.0563 (12)0.0641 (11)0.0531 (11)0.0032 (9)0.0063 (9)0.0002 (9)
Geometric parameters (Å, º) top
O1A—C9A1.224 (2)O1B—C9B1.222 (2)
N1A—N2A1.302 (2)N1B—N2B1.304 (2)
N1A—C10A1.360 (2)N1B—C10B1.355 (2)
N2A—N3A1.362 (2)N2B—N3B1.359 (2)
N3A—C11A1.340 (2)N3B—C11B1.343 (2)
N3A—C13A1.454 (3)N3B—C13B1.454 (2)
C1A—C6A1.390 (3)C1B—C6B1.386 (3)
C1A—C2A1.403 (5)C1B—C2B1.392 (3)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.358 (5)C2B—C3B1.370 (4)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.356 (5)C3B—C4B1.373 (4)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.374 (4)C4B—C5B1.379 (3)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.391 (3)C5B—C6B1.390 (3)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.456 (3)C6B—C7B1.454 (3)
C7A—C8A1.326 (3)C7B—C8B1.326 (3)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.470 (3)C8B—C9B1.474 (3)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.471 (3)C9B—C10B1.471 (3)
C10A—C11A1.380 (3)C10B—C11B1.382 (2)
C11A—C12A1.484 (3)C11B—C12B1.478 (3)
C12A—H12A0.9600C12B—H12D0.9600
C12A—H12B0.9600C12B—H12E0.9600
C12A—H12C0.9600C12B—H12F0.9600
C13A—C14A1.508 (3)C13B—C14B1.504 (2)
C13A—H13A0.9700C13B—H13C0.9700
C13A—H13B0.9700C13B—H13D0.9700
C14A—C19A1.369 (3)C14B—C19B1.385 (3)
C14A—C15A1.370 (3)C14B—C15B1.389 (3)
C15A—C16A1.382 (3)C15B—C16B1.382 (3)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.368 (4)C16B—C17B1.372 (4)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.359 (4)C17B—C18B1.362 (3)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.378 (3)C18B—C19B1.372 (3)
C18A—H18A0.9300C18B—H18B0.9300
C19A—H19A0.9300C19B—H19B0.9300
N2A—N1A—C10A109.19 (16)N2B—N1B—C10B109.54 (15)
N1A—N2A—N3A106.85 (16)N1B—N2B—N3B106.65 (15)
C11A—N3A—N2A111.31 (16)C11B—N3B—N2B111.36 (15)
C11A—N3A—C13A129.11 (18)C11B—N3B—C13B129.29 (16)
N2A—N3A—C13A119.57 (17)N2B—N3B—C13B119.34 (15)
C6A—C1A—C2A119.3 (3)C6B—C1B—C2B120.4 (2)
C6A—C1A—H1AA120.4C6B—C1B—H1BA119.8
C2A—C1A—H1AA120.4C2B—C1B—H1BA119.8
C3A—C2A—C1A121.3 (3)C3B—C2B—C1B120.5 (2)
C3A—C2A—H2AA119.3C3B—C2B—H2BA119.8
C1A—C2A—H2AA119.3C1B—C2B—H2BA119.8
C4A—C3A—C2A119.4 (3)C2B—C3B—C4B119.8 (2)
C4A—C3A—H3AA120.3C2B—C3B—H3BA120.1
C2A—C3A—H3AA120.3C4B—C3B—H3BA120.1
C3A—C4A—C5A120.9 (3)C3B—C4B—C5B120.1 (3)
C3A—C4A—H4AA119.6C3B—C4B—H4BA119.9
C5A—C4A—H4AA119.6C5B—C4B—H4BA119.9
C4A—C5A—C6A121.2 (3)C4B—C5B—C6B121.2 (2)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.4
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.4
C1A—C6A—C5A117.9 (2)C1B—C6B—C5B118.10 (19)
C1A—C6A—C7A118.9 (2)C1B—C6B—C7B119.10 (19)
C5A—C6A—C7A123.2 (2)C5B—C6B—C7B122.80 (17)
C8A—C7A—C6A127.7 (2)C8B—C7B—C6B127.70 (19)
C8A—C7A—H7AA116.1C8B—C7B—H7BA116.2
C6A—C7A—H7AA116.1C6B—C7B—H7BA116.2
C7A—C8A—C9A122.02 (19)C7B—C8B—C9B121.24 (18)
C7A—C8A—H8AA119.0C7B—C8B—H8BA119.4
C9A—C8A—H8AA119.0C9B—C8B—H8BA119.4
O1A—C9A—C8A122.50 (17)O1B—C9B—C10B120.71 (16)
O1A—C9A—C10A121.08 (17)O1B—C9B—C8B122.92 (17)
C8A—C9A—C10A116.41 (17)C10B—C9B—C8B116.36 (16)
N1A—C10A—C11A108.70 (16)N1B—C10B—C11B108.57 (15)
N1A—C10A—C9A121.82 (17)N1B—C10B—C9B122.18 (16)
C11A—C10A—C9A129.47 (18)C11B—C10B—C9B129.23 (16)
N3A—C11A—C10A103.95 (17)N3B—C11B—C10B103.88 (15)
N3A—C11A—C12A122.85 (18)N3B—C11B—C12B122.95 (16)
C10A—C11A—C12A133.19 (18)C10B—C11B—C12B133.17 (17)
C11A—C12A—H12A109.5C11B—C12B—H12D109.5
C11A—C12A—H12B109.5C11B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C11A—C12A—H12C109.5C11B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
N3A—C13A—C14A114.42 (17)N3B—C13B—C14B113.13 (15)
N3A—C13A—H13A108.7N3B—C13B—H13C109.0
C14A—C13A—H13A108.7C14B—C13B—H13C109.0
N3A—C13A—H13B108.7N3B—C13B—H13D109.0
C14A—C13A—H13B108.7C14B—C13B—H13D109.0
H13A—C13A—H13B107.6H13C—C13B—H13D107.8
C19A—C14A—C15A118.16 (18)C19B—C14B—C15B118.23 (17)
C19A—C14A—C13A123.90 (18)C19B—C14B—C13B120.04 (17)
C15A—C14A—C13A117.86 (18)C15B—C14B—C13B121.65 (17)
C14A—C15A—C16A120.8 (2)C16B—C15B—C14B120.4 (2)
C14A—C15A—H15A119.6C16B—C15B—H15B119.8
C16A—C15A—H15A119.6C14B—C15B—H15B119.8
C17A—C16A—C15A120.3 (2)C17B—C16B—C15B119.9 (2)
C17A—C16A—H16A119.9C17B—C16B—H16B120.0
C15A—C16A—H16A119.9C15B—C16B—H16B120.0
C18A—C17A—C16A119.3 (2)C18B—C17B—C16B120.3 (2)
C18A—C17A—H17A120.4C18B—C17B—H17B119.8
C16A—C17A—H17A120.4C16B—C17B—H17B119.8
C17A—C18A—C19A120.3 (2)C17B—C18B—C19B120.1 (2)
C17A—C18A—H18A119.9C17B—C18B—H18B119.9
C19A—C18A—H18A119.9C19B—C18B—H18B119.9
C14A—C19A—C18A121.2 (2)C18B—C19B—C14B121.0 (2)
C14A—C19A—H19A119.4C18B—C19B—H19B119.5
C18A—C19A—H19A119.4C14B—C19B—H19B119.5
C10A—N1A—N2A—N3A0.5 (2)C10B—N1B—N2B—N3B0.2 (2)
N1A—N2A—N3A—C11A0.2 (2)N1B—N2B—N3B—C11B0.3 (2)
N1A—N2A—N3A—C13A178.98 (16)N1B—N2B—N3B—C13B179.68 (15)
C6A—C1A—C2A—C3A1.3 (5)C6B—C1B—C2B—C3B0.1 (3)
C1A—C2A—C3A—C4A0.1 (5)C1B—C2B—C3B—C4B0.0 (4)
C2A—C3A—C4A—C5A0.5 (5)C2B—C3B—C4B—C5B0.2 (4)
C3A—C4A—C5A—C6A0.6 (4)C3B—C4B—C5B—C6B0.5 (3)
C2A—C1A—C6A—C5A2.4 (3)C2B—C1B—C6B—C5B0.4 (3)
C2A—C1A—C6A—C7A177.2 (2)C2B—C1B—C6B—C7B179.32 (18)
C4A—C5A—C6A—C1A2.1 (3)C4B—C5B—C6B—C1B0.6 (3)
C4A—C5A—C6A—C7A177.5 (2)C4B—C5B—C6B—C7B179.11 (18)
C1A—C6A—C7A—C8A170.40 (19)C1B—C6B—C7B—C8B174.84 (18)
C5A—C6A—C7A—C8A9.2 (3)C5B—C6B—C7B—C8B5.4 (3)
C6A—C7A—C8A—C9A176.99 (17)C6B—C7B—C8B—C9B178.79 (16)
C7A—C8A—C9A—O1A2.8 (3)C7B—C8B—C9B—O1B6.5 (3)
C7A—C8A—C9A—C10A177.47 (16)C7B—C8B—C9B—C10B174.80 (16)
N2A—N1A—C10A—C11A0.6 (2)N2B—N1B—C10B—C11B0.1 (2)
N2A—N1A—C10A—C9A178.32 (16)N2B—N1B—C10B—C9B179.03 (16)
O1A—C9A—C10A—N1A177.83 (18)O1B—C9B—C10B—N1B179.47 (17)
C8A—C9A—C10A—N1A1.9 (2)C8B—C9B—C10B—N1B0.8 (2)
O1A—C9A—C10A—C11A3.5 (3)O1B—C9B—C10B—C11B1.8 (3)
C8A—C9A—C10A—C11A176.79 (17)C8B—C9B—C10B—C11B179.48 (16)
N2A—N3A—C11A—C10A0.2 (2)N2B—N3B—C11B—C10B0.22 (19)
C13A—N3A—C11A—C10A178.45 (17)C13B—N3B—C11B—C10B179.73 (16)
N2A—N3A—C11A—C12A179.62 (17)N2B—N3B—C11B—C12B179.80 (17)
C13A—N3A—C11A—C12A1.0 (3)C13B—N3B—C11B—C12B0.3 (3)
N1A—C10A—C11A—N3A0.46 (19)N1B—C10B—C11B—N3B0.09 (19)
C9A—C10A—C11A—N3A178.38 (17)C9B—C10B—C11B—N3B178.77 (16)
N1A—C10A—C11A—C12A179.8 (2)N1B—C10B—C11B—C12B179.93 (19)
C9A—C10A—C11A—C12A1.0 (3)C9B—C10B—C11B—C12B1.2 (3)
C11A—N3A—C13A—C14A82.2 (3)C11B—N3B—C13B—C14B74.4 (2)
N2A—N3A—C13A—C14A99.3 (2)N2B—N3B—C13B—C14B105.67 (19)
N3A—C13A—C14A—C19A20.1 (3)N3B—C13B—C14B—C19B135.50 (18)
N3A—C13A—C14A—C15A163.1 (2)N3B—C13B—C14B—C15B48.0 (3)
C19A—C14A—C15A—C16A0.9 (3)C19B—C14B—C15B—C16B0.7 (3)
C13A—C14A—C15A—C16A176.1 (2)C13B—C14B—C15B—C16B177.32 (19)
C14A—C15A—C16A—C17A0.2 (4)C14B—C15B—C16B—C17B0.7 (3)
C15A—C16A—C17A—C18A1.5 (4)C15B—C16B—C17B—C18B0.1 (4)
C16A—C17A—C18A—C19A1.7 (4)C16B—C17B—C18B—C19B0.8 (4)
C15A—C14A—C19A—C18A0.6 (4)C17B—C18B—C19B—C14B0.7 (3)
C13A—C14A—C19A—C18A176.2 (2)C15B—C14B—C19B—C18B0.0 (3)
C17A—C18A—C19A—C14A0.7 (4)C13B—C14B—C19B—C18B176.67 (19)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C14A–C19A and C14B–C19B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C13A—H13A···N1Bi0.972.503.453 (3)166
C1B—H1BA···Cg1ii0.932.973.893 (3)174
C13B—H13C···Cg2iii0.972.613.528 (2)159
Symmetry codes: (i) x, y+1, z; (ii) x, y+1/2, z+1/2; (iii) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC19H17N3O
Mr303.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)12.3117 (14), 13.8016 (15), 19.312 (2)
β (°) 99.665 (2)
V3)3235.0 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.46 × 0.33 × 0.11
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.965, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
32508, 9403, 4890
Rint0.042
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.219, 1.03
No. of reflections9403
No. of parameters417
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.28

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

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C14A–C19A and C14B–C19B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C13A—H13A···N1Bi0.972.503.453 (3)166
C1B—H1BA···Cg1ii0.932.973.893 (3)174
C13B—H13C···Cg2iii0.972.613.528 (2)159
Symmetry codes: (i) x, y+1, z; (ii) x, y+1/2, z+1/2; (iii) x+1, y+2, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

First citationBallesteros, J. F., Sanz, M. J., Ubeda, A., Miranda, M. A., Iborra, S., Paya, M. & Alcaraz, M. J. (1995). J. Med. Chem. 38, 2794–2797.  CrossRef CAS PubMed Web of Science Google Scholar
First citationBanerjee, A., Nayak, P. L. & Rout, M. K. (1996). J. Indian Chem. Soc. 43, 578–82.  Google Scholar
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKothari, S., Vyas, R. & Verma, B. L. (1999). Indian J. Heteroat. Chem. 8, 285–288.  CAS Google Scholar
First citationLaliberte, R., Campbell, D. J. & Bruderlein, F. (1967). Can. J. Pharm. Sci. 2, 37–43.  CAS Google Scholar
First citationNagaraj, A. & Reddy, C. S. J. (2007). Heteroat. Chem. 44, 1181–1185.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSuwa, T., Fukushima, K. & Kyogoku, K. (1984). Jpn J. Pharm. 34, 89–94.  CrossRef CAS Google Scholar

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