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

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ISSN: 2056-9890

4-[Amino­(3-methyl­phen­yl)methyl­­idene]-2-(3-methyl­phen­yl)-1H-imidazol-5(4H)-one ethanol hemisolvate

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore, India 570 006, and bDepartment of Chemistry, Calicut University, Kerala, India 673635
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

(Received 17 December 2012; accepted 21 December 2012; online 4 January 2013)

In the title compound, C18H17N3O·0.5C2H5OH, the dihedral angles between the central imidazole rings and the pendant benzene rings are 42.06 (15) and 2.01 (16)° in one asymmetric mol­ecule and 47.91 (15) and 7.31 (14)° in the other. An intra­molecular N—H⋯O hydrogen bond occurs in each imidazole mol­ecule. In the crystal, the components are connected by O—H⋯N, N—H⋯O, C—H⋯O and N—H⋯N hydrogen bonds. Weak aromatic ππ inter­actions also occur [shortest centroid–centroid distance = 3.684 (3) Å].

Related literature

For background to imidazoles, see: Shi et al. (2011[Shi, F., Zeng, X.-N., Wu, F.-Y., Yan, S., Zheng, W.-F. & Tu, S.-J. (2011). J. Heterocycl. Chem. 49, 59-63.]). For a related structure, see: Chang et al. (2012[Chang, M.-J., Tsai, H.-Y., Fang, T.-C., Luo, M.-H. & Chen, K.-Y. (2012). Acta Cryst. E68, o902-o903.]). For further synthetic details, see: Shafi et al. (2005[Shafi, P. M., Sobha, T. D. & Basheer, P. A. M. (2005). Indian J. Chem. Sect. B, 44, 1298-1300.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17N3O·0.5C2H6O

  • Mr = 314.38

  • Triclinic, [P \overline 1]

  • a = 8.227 (4) Å

  • b = 13.505 (7) Å

  • c = 16.044 (8) Å

  • α = 87.451 (8)°

  • β = 78.869 (9)°

  • γ = 80.241 (9)°

  • V = 1723.6 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 300 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Oxford Diffraction Xcalibur CCD diffractometer

  • 16691 measured reflections

  • 6512 independent reflections

  • 4294 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.227

  • S = 1.02

  • 6512 reflections

  • 430 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 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
N3B—H3B1⋯O1B 0.86 2.07 2.748 (3) 135
O2—H2⋯N1B 1.09 1.84 2.917 (3) 170
N3B—H3B2⋯N1A 0.86 2.37 3.033 (3) 134
N2A—H2A⋯O1Ai 0.86 1.95 2.803 (3) 170
N2B—H2B⋯O1Bii 0.86 1.97 2.805 (3) 164
N3A—H3A1⋯O1A 0.86 2.12 2.783 (3) 134
N3A—H3A2⋯O2iii 0.86 2.02 2.857 (3) 163
C12A—H12A⋯O1Ai 0.93 2.59 3.492 (4) 164
C12B—H12B⋯O1Bii 0.93 2.54 3.455 (3) 168
C16B—H16B⋯O2 0.93 2.37 3.284 (4) 168
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: Mercury.

Supporting information


Comment top

Imidazole derivatives exhibits various bioactivities (Shi et al., 2011). As part of our studies in the area, we now report the structure of the title solvate, (I).

The asymmetric unit consists of two symmetry-independent molecules (A and B) of the title compound and the solvent molecule (ethanol) as shown in Fig. 1. The conformations of the two molecules are almost same which is confirmed by the dihedral angles [42.72 (14)° and 41.46 (15)° between aromatic rings of molecule A and molecule B, respectively]. The geometry of the compound is similar to (Z)-4-(2-Hydroxybenzylidene)-1-methyl-2-phenyl-1H-imidazol-5(4H)-one (Chang et al., 2012).

The molecules are connected by hydrogen bonds of the type N—H···O, C—H···O and N—H···N (Fig. 2.). Table 1 shows the geometry of intramolecular and intermolecular hydrogen bond. In addition, weak interactions ππ occur [shortest centroid-centroid distance = 3.684 (3) Å].

Related literature top

For background to imidazoles, see: Shi et al. (2011). For a related structure, see: Chang et al. (2012). For further synthetic details, see: Shafi et al. (2005).

Experimental top

The title molecule was synthesized according to the reported procedure (Shafi et al., 2005) and yellow blocks were recrystallized from ethanol solution.

Refinement top

All the hydrogen atoms of the compound are fixed geometrically (N—H = 0.86 and C—H= 0.93–0.97 Å) and allowed to ride on their parent atoms. The H2 atom on O2 atom is located in a difference Fourier map and isotropically refined.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of the title compound with 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed along the crystallographic a axis.
4-[Amino(3-methylphenyl)methylidene]-2-(3-methylphenyl)-1H-imidazol- 5(4H)-one ethanol hemisolvate top
Crystal data top
C18H17N3O·0.5C2H6OZ = 4
Mr = 314.38F(000) = 668
Triclinic, P1Dx = 1.212 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.227 (4) ÅCell parameters from 6512 reflections
b = 13.505 (7) Åθ = 1.3–25.7°
c = 16.044 (8) ŵ = 0.08 mm1
α = 87.451 (8)°T = 300 K
β = 78.869 (9)°Block, yellow
γ = 80.241 (9)°0.23 × 0.22 × 0.21 mm
V = 1723.6 (15) Å3
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
4294 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 25.7°, θmin = 1.3°
Detector resolution: 16.0839 pixels mm-1h = 1010
ω scansk = 1616
16691 measured reflectionsl = 1919
6512 independent reflections
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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1503P)2]
where P = (Fo2 + 2Fc2)/3
6512 reflections(Δ/σ)max < 0.001
430 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C18H17N3O·0.5C2H6Oγ = 80.241 (9)°
Mr = 314.38V = 1723.6 (15) Å3
Triclinic, P1Z = 4
a = 8.227 (4) ÅMo Kα radiation
b = 13.505 (7) ŵ = 0.08 mm1
c = 16.044 (8) ÅT = 300 K
α = 87.451 (8)°0.23 × 0.22 × 0.21 mm
β = 78.869 (9)°
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
4294 reflections with I > 2σ(I)
16691 measured reflectionsRint = 0.049
6512 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.227H-atom parameters constrained
S = 1.02Δρmax = 0.35 e Å3
6512 reflectionsΔρmin = 0.28 e Å3
430 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1A0.0441 (2)0.99511 (11)0.39005 (10)0.0627 (6)
N1A0.1176 (3)0.73476 (13)0.39638 (11)0.0513 (6)
N2A0.0766 (3)0.87156 (13)0.47653 (11)0.0512 (6)
N3A0.0639 (3)0.90481 (13)0.24056 (12)0.0605 (8)
C1A0.0191 (3)0.90522 (15)0.40432 (13)0.0483 (7)
C2A0.1360 (3)0.76943 (16)0.46836 (13)0.0491 (8)
C3A0.0423 (3)0.81787 (15)0.35360 (13)0.0474 (7)
C4A0.0054 (3)0.81766 (16)0.27501 (14)0.0494 (8)
C5A0.0080 (3)0.72533 (16)0.22539 (15)0.0534 (8)
C6A0.0597 (3)0.72778 (17)0.13764 (15)0.0561 (9)
C7A0.0713 (4)0.64447 (19)0.08829 (17)0.0655 (10)
C8A0.0268 (4)0.5581 (2)0.1294 (2)0.0849 (15)
C9A0.0246 (4)0.5539 (2)0.2159 (2)0.0839 (13)
C10A0.0332 (4)0.63688 (18)0.26547 (18)0.0681 (10)
C11A0.2082 (3)0.70925 (17)0.53471 (14)0.0568 (8)
C12A0.2279 (3)0.7520 (2)0.60806 (15)0.0658 (9)
C13A0.2944 (4)0.6950 (3)0.67236 (18)0.0857 (13)
C14A0.3427 (5)0.5938 (3)0.6602 (2)0.1033 (16)
C15A0.3267 (5)0.5506 (3)0.5874 (3)0.1066 (16)
C16A0.2582 (4)0.6063 (2)0.52386 (19)0.0822 (13)
C17A0.1312 (5)0.6476 (2)0.00652 (18)0.0885 (13)
C18A0.3093 (6)0.7438 (4)0.7527 (2)0.134 (2)
O1B0.4531 (2)0.52071 (12)0.11551 (9)0.0627 (7)
N1B0.6174 (3)0.74818 (12)0.07227 (11)0.0476 (6)
N2B0.5866 (3)0.61392 (13)0.00437 (11)0.0538 (7)
N3B0.3968 (3)0.62791 (13)0.26286 (11)0.0549 (7)
C1B0.5175 (3)0.59695 (16)0.08761 (13)0.0489 (7)
C2B0.6424 (3)0.70466 (15)0.00143 (13)0.0456 (7)
C3B0.5359 (3)0.68378 (15)0.13094 (13)0.0452 (7)
C4B0.4739 (3)0.69788 (15)0.21746 (13)0.0453 (7)
C5B0.4914 (3)0.78375 (16)0.26738 (14)0.0495 (8)
C6B0.5509 (3)0.76373 (19)0.34345 (14)0.0569 (9)
C7B0.5657 (4)0.8387 (2)0.39569 (16)0.0722 (11)
C8B0.5185 (5)0.9354 (2)0.3714 (2)0.0912 (14)
C9B0.4569 (5)0.9589 (2)0.2971 (2)0.0895 (15)
C10B0.4438 (4)0.88250 (18)0.24354 (18)0.0703 (10)
C11B0.7173 (3)0.74460 (16)0.08466 (14)0.0493 (8)
C12B0.7199 (3)0.69606 (19)0.15940 (14)0.0580 (9)
C13B0.7846 (4)0.7339 (2)0.23907 (15)0.0660 (10)
C14B0.8467 (4)0.8231 (2)0.24228 (18)0.0792 (11)
C15B0.8488 (4)0.8717 (2)0.1686 (2)0.0849 (13)
C16B0.7855 (4)0.83274 (19)0.08983 (17)0.0707 (10)
C17B0.6310 (5)0.8138 (3)0.47749 (18)0.1048 (18)
C18B0.7868 (5)0.6790 (3)0.31937 (18)0.1035 (15)
O20.7675 (3)0.92206 (12)0.09939 (11)0.0719 (7)
C190.6601 (5)1.0132 (2)0.0840 (2)0.0910 (13)
C200.7531 (6)1.0820 (3)0.0319 (3)0.139 (2)
H2A0.076000.907500.519600.0610*
H3A10.071700.960000.266900.0730*
H3A20.093900.905800.192000.0730*
H6A0.087300.787100.111400.0670*
H8A0.031900.501300.097600.1020*
H9A0.054000.494800.241600.1000*
H10A0.065800.633500.324200.0820*
H12A0.195800.821000.614900.0790*
H14A0.386800.554000.701900.1240*
H15A0.362800.481900.580100.1280*
H16A0.246200.575400.475200.0990*
H17A0.183200.581600.026100.1330*
H17B0.211300.692800.020100.1330*
H17C0.037300.670600.033800.1330*
H18A0.203800.784200.775800.2000*
H18B0.394800.785500.740000.2000*
H18C0.338600.692800.793300.2000*
H3B10.385700.574600.238600.0660*
H3B20.358400.636300.316300.0660*
H2B0.593700.574400.037200.0650*
H6B0.581700.697200.359400.0680*
H8B0.527900.987300.405500.1090*
H9B0.424001.025800.282700.1070*
H10B0.404100.897800.193200.0850*
H12B0.677100.636200.156300.0700*
H14B0.887700.850700.294700.0950*
H15B0.893100.931000.171800.1020*
H16B0.788500.865500.040500.0850*
H17D0.671600.870800.494600.1570*
H17E0.720900.757600.468600.1570*
H17F0.541900.797100.521100.1570*
H18D0.703400.714900.348900.1560*
H18E0.762600.612600.305100.1560*
H18F0.895600.674700.355100.1560*
H20.700600.859800.095200.100 (10)*
H19A0.606001.044500.137700.1090*
H19B0.573200.997900.055800.1090*
H20A0.828801.104300.062800.2090*
H20B0.676601.138900.016900.2090*
H20C0.815901.048800.018900.2090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.1029 (15)0.0380 (8)0.0485 (9)0.0014 (8)0.0286 (9)0.0005 (7)
N1A0.0665 (14)0.0413 (9)0.0399 (10)0.0003 (9)0.0033 (9)0.0015 (8)
N2A0.0741 (14)0.0424 (10)0.0350 (9)0.0013 (9)0.0125 (9)0.0011 (7)
N3A0.0969 (17)0.0400 (10)0.0477 (11)0.0039 (10)0.0271 (11)0.0022 (8)
C1A0.0656 (16)0.0411 (11)0.0374 (11)0.0052 (10)0.0120 (10)0.0032 (9)
C2A0.0575 (16)0.0434 (11)0.0383 (12)0.0016 (10)0.0018 (10)0.0026 (9)
C3A0.0608 (16)0.0401 (11)0.0385 (11)0.0029 (10)0.0073 (10)0.0009 (9)
C4A0.0617 (16)0.0419 (11)0.0436 (12)0.0087 (10)0.0076 (11)0.0009 (9)
C5A0.0607 (17)0.0447 (12)0.0555 (14)0.0047 (11)0.0149 (12)0.0060 (10)
C6A0.0714 (18)0.0470 (12)0.0521 (14)0.0044 (11)0.0204 (12)0.0060 (10)
C7A0.0744 (19)0.0567 (15)0.0693 (17)0.0011 (13)0.0275 (14)0.0178 (12)
C8A0.101 (3)0.0562 (16)0.104 (3)0.0092 (15)0.032 (2)0.0304 (16)
C9A0.102 (3)0.0511 (15)0.103 (2)0.0284 (15)0.016 (2)0.0026 (15)
C10A0.080 (2)0.0510 (14)0.0725 (18)0.0167 (13)0.0069 (14)0.0009 (12)
C11A0.0572 (16)0.0570 (13)0.0443 (13)0.0059 (11)0.0032 (11)0.0131 (10)
C12A0.0644 (18)0.0803 (17)0.0419 (13)0.0123 (13)0.0066 (12)0.0088 (12)
C13A0.061 (2)0.127 (3)0.0538 (17)0.0172 (18)0.0069 (14)0.0219 (17)
C14A0.090 (3)0.122 (3)0.075 (2)0.021 (2)0.0047 (18)0.050 (2)
C15A0.129 (3)0.072 (2)0.096 (3)0.0235 (19)0.008 (2)0.0330 (19)
C16A0.110 (3)0.0532 (15)0.0663 (17)0.0128 (15)0.0003 (16)0.0127 (13)
C17A0.118 (3)0.0807 (19)0.0674 (19)0.0051 (19)0.0315 (19)0.0282 (15)
C18A0.124 (4)0.204 (5)0.063 (2)0.032 (3)0.046 (2)0.006 (3)
O1B0.0975 (15)0.0513 (9)0.0395 (9)0.0283 (9)0.0016 (8)0.0036 (7)
N1B0.0592 (13)0.0415 (9)0.0422 (10)0.0075 (8)0.0107 (9)0.0008 (7)
N2B0.0795 (15)0.0466 (10)0.0353 (10)0.0181 (10)0.0031 (9)0.0044 (7)
N3B0.0820 (16)0.0425 (10)0.0365 (10)0.0093 (10)0.0023 (9)0.0032 (8)
C1B0.0652 (16)0.0449 (11)0.0358 (11)0.0106 (11)0.0061 (10)0.0012 (9)
C2B0.0515 (15)0.0433 (11)0.0414 (12)0.0081 (10)0.0072 (10)0.0010 (9)
C3B0.0567 (15)0.0409 (11)0.0384 (11)0.0097 (10)0.0087 (10)0.0003 (8)
C4B0.0549 (15)0.0401 (10)0.0392 (11)0.0011 (10)0.0119 (10)0.0017 (9)
C5B0.0564 (16)0.0433 (11)0.0451 (12)0.0024 (10)0.0038 (10)0.0074 (9)
C6B0.0665 (18)0.0626 (14)0.0410 (13)0.0128 (12)0.0053 (11)0.0061 (10)
C7B0.083 (2)0.085 (2)0.0476 (15)0.0267 (16)0.0057 (13)0.0210 (13)
C8B0.117 (3)0.082 (2)0.073 (2)0.0251 (19)0.0020 (19)0.0369 (17)
C9B0.110 (3)0.0435 (14)0.106 (3)0.0006 (15)0.004 (2)0.0215 (15)
C10B0.088 (2)0.0490 (13)0.0680 (17)0.0001 (13)0.0087 (15)0.0048 (12)
C11B0.0511 (15)0.0500 (12)0.0452 (12)0.0055 (10)0.0085 (10)0.0043 (9)
C12B0.0640 (17)0.0655 (14)0.0451 (13)0.0166 (12)0.0081 (11)0.0062 (11)
C13B0.0658 (19)0.0851 (18)0.0425 (13)0.0078 (14)0.0058 (12)0.0111 (12)
C14B0.082 (2)0.085 (2)0.0573 (17)0.0067 (16)0.0083 (14)0.0228 (15)
C15B0.102 (3)0.0668 (17)0.078 (2)0.0282 (17)0.0131 (17)0.0088 (15)
C16B0.093 (2)0.0562 (14)0.0600 (16)0.0221 (14)0.0012 (14)0.0013 (12)
C17B0.113 (3)0.165 (4)0.0477 (17)0.052 (3)0.0131 (17)0.0209 (19)
C18B0.121 (3)0.147 (3)0.0449 (16)0.040 (3)0.0064 (17)0.0003 (18)
O20.1014 (15)0.0543 (10)0.0702 (12)0.0129 (10)0.0422 (11)0.0041 (8)
C190.110 (3)0.0644 (17)0.101 (2)0.0073 (17)0.034 (2)0.0074 (16)
C200.144 (4)0.073 (2)0.189 (5)0.012 (2)0.019 (3)0.047 (3)
Geometric parameters (Å, º) top
O1A—C1A1.266 (3)C16A—H16A0.9300
O1B—C1B1.262 (3)C17A—H17B0.9600
O2—C191.430 (4)C17A—H17C0.9600
O2—H21.0900C17A—H17A0.9600
N1A—C3A1.405 (3)C18A—H18C0.9600
N1A—C2A1.310 (3)C18A—H18B0.9600
N2A—C2A1.386 (3)C18A—H18A0.9600
N2A—C1A1.366 (3)C1B—C3B1.433 (3)
N3A—C4A1.332 (3)C2B—C11B1.478 (3)
N2A—H2A0.8600C3B—C4B1.393 (3)
N3A—H3A20.8600C4B—C5B1.480 (3)
N3A—H3A10.8600C5B—C6B1.400 (3)
N1B—C3B1.405 (3)C5B—C10B1.383 (3)
N1B—C2B1.309 (3)C6B—C7B1.378 (4)
N2B—C2B1.373 (3)C7B—C8B1.360 (4)
N2B—C1B1.372 (3)C7B—C17B1.515 (4)
N3B—C4B1.338 (3)C8B—C9B1.387 (5)
N2B—H2B0.8600C9B—C10B1.403 (4)
N3B—H3B10.8600C11B—C16B1.392 (4)
N3B—H3B20.8600C11B—C12B1.387 (3)
C1A—C3A1.428 (3)C12B—C13B1.396 (3)
C2A—C11A1.466 (3)C13B—C18B1.510 (4)
C3A—C4A1.391 (3)C13B—C14B1.381 (4)
C4A—C5A1.486 (3)C14B—C15B1.382 (4)
C5A—C10A1.393 (3)C15B—C16B1.387 (4)
C5A—C6A1.391 (3)C6B—H6B0.9300
C6A—C7A1.384 (4)C8B—H8B0.9300
C7A—C17A1.507 (4)C9B—H9B0.9300
C7A—C8A1.383 (4)C10B—H10B0.9300
C8A—C9A1.372 (5)C12B—H12B0.9300
C9A—C10A1.387 (4)C14B—H14B0.9300
C11A—C16A1.390 (4)C15B—H15B0.9300
C11A—C12A1.382 (3)C16B—H16B0.9300
C12A—C13A1.400 (4)C17B—H17F0.9600
C13A—C14A1.369 (6)C17B—H17D0.9600
C13A—C18A1.508 (5)C17B—H17E0.9600
C14A—C15A1.367 (6)C18B—H18E0.9600
C15A—C16A1.390 (5)C18B—H18D0.9600
C6A—H6A0.9300C18B—H18F0.9600
C8A—H8A0.9300C19—C201.440 (6)
C9A—H9A0.9300C19—H19A0.9700
C10A—H10A0.9300C19—H19B0.9700
C12A—H12A0.9300C20—H20A0.9600
C14A—H14A0.9300C20—H20B0.9600
C15A—H15A0.9300C20—H20C0.9600
C19—O2—H2108.00H18A—C18A—H18B110.00
C2A—N1A—C3A105.64 (17)O1B—C1B—N2B125.39 (19)
C1A—N2A—C2A108.07 (17)O1B—C1B—C3B130.48 (19)
C1A—N2A—H2A126.00N2B—C1B—C3B104.13 (18)
C2A—N2A—H2A126.00N2B—C2B—C11B120.62 (18)
C4A—N3A—H3A1120.00N1B—C2B—N2B112.56 (19)
C4A—N3A—H3A2120.00N1B—C2B—C11B126.8 (2)
H3A1—N3A—H3A2120.00C1B—C3B—C4B122.2 (2)
C2B—N1B—C3B105.51 (18)N1B—C3B—C1B109.22 (17)
C1B—N2B—C2B108.56 (17)N1B—C3B—C4B128.51 (19)
C2B—N2B—H2B126.00N3B—C4B—C3B119.66 (19)
C1B—N2B—H2B126.00N3B—C4B—C5B114.64 (18)
C4B—N3B—H3B2120.00C3B—C4B—C5B125.7 (2)
H3B1—N3B—H3B2120.00C4B—C5B—C6B118.5 (2)
C4B—N3B—H3B1120.00C4B—C5B—C10B122.4 (2)
O1A—C1A—N2A125.16 (19)C6B—C5B—C10B119.1 (2)
O1A—C1A—C3A129.9 (2)C5B—C6B—C7B122.6 (2)
N2A—C1A—C3A104.90 (17)C6B—C7B—C8B117.6 (3)
N2A—C2A—C11A122.44 (19)C8B—C7B—C17B121.4 (3)
N1A—C2A—C11A125.3 (2)C6B—C7B—C17B121.0 (3)
N1A—C2A—N2A112.28 (19)C7B—C8B—C9B121.9 (3)
N1A—C3A—C1A109.09 (18)C8B—C9B—C10B120.5 (3)
C1A—C3A—C4A124.12 (19)C5B—C10B—C9B118.4 (3)
N1A—C3A—C4A126.79 (19)C12B—C11B—C16B118.4 (2)
C3A—C4A—C5A123.8 (2)C2B—C11B—C12B121.0 (2)
N3A—C4A—C3A119.0 (2)C2B—C11B—C16B120.6 (2)
N3A—C4A—C5A117.2 (2)C11B—C12B—C13B122.3 (2)
C4A—C5A—C10A120.9 (2)C12B—C13B—C18B121.1 (3)
C4A—C5A—C6A119.5 (2)C12B—C13B—C14B118.0 (2)
C6A—C5A—C10A119.6 (2)C14B—C13B—C18B120.9 (3)
C5A—C6A—C7A121.9 (2)C13B—C14B—C15B120.8 (3)
C8A—C7A—C17A121.3 (2)C14B—C15B—C16B120.6 (3)
C6A—C7A—C8A117.5 (2)C11B—C16B—C15B120.0 (2)
C6A—C7A—C17A121.3 (2)C7B—C6B—H6B119.00
C7A—C8A—C9A121.7 (3)C5B—C6B—H6B119.00
C8A—C9A—C10A120.8 (3)C7B—C8B—H8B119.00
C5A—C10A—C9A118.6 (3)C9B—C8B—H8B119.00
C2A—C11A—C12A121.8 (2)C10B—C9B—H9B120.00
C2A—C11A—C16A119.3 (2)C8B—C9B—H9B120.00
C12A—C11A—C16A118.9 (2)C5B—C10B—H10B121.00
C11A—C12A—C13A122.3 (3)C9B—C10B—H10B121.00
C14A—C13A—C18A121.5 (3)C13B—C12B—H12B119.00
C12A—C13A—C18A120.8 (4)C11B—C12B—H12B119.00
C12A—C13A—C14A117.7 (3)C13B—C14B—H14B120.00
C13A—C14A—C15A120.7 (3)C15B—C14B—H14B120.00
C14A—C15A—C16A122.0 (4)C14B—C15B—H15B120.00
C11A—C16A—C15A118.4 (3)C16B—C15B—H15B120.00
C7A—C6A—H6A119.00C15B—C16B—H16B120.00
C5A—C6A—H6A119.00C11B—C16B—H16B120.00
C9A—C8A—H8A119.00C7B—C17B—H17E109.00
C7A—C8A—H8A119.00C7B—C17B—H17F109.00
C8A—C9A—H9A120.00C7B—C17B—H17D110.00
C10A—C9A—H9A120.00H17D—C17B—H17F109.00
C9A—C10A—H10A121.00H17E—C17B—H17F109.00
C5A—C10A—H10A121.00H17D—C17B—H17E109.00
C13A—C12A—H12A119.00C13B—C18B—H18E109.00
C11A—C12A—H12A119.00C13B—C18B—H18F109.00
C15A—C14A—H14A120.00H18D—C18B—H18E109.00
C13A—C14A—H14A120.00H18D—C18B—H18F109.00
C14A—C15A—H15A119.00H18E—C18B—H18F110.00
C16A—C15A—H15A119.00C13B—C18B—H18D109.00
C11A—C16A—H16A121.00O2—C19—C20111.2 (3)
C15A—C16A—H16A121.00O2—C19—H19A109.00
C7A—C17A—H17C109.00O2—C19—H19B109.00
C7A—C17A—H17B109.00C20—C19—H19A109.00
H17A—C17A—H17C109.00C20—C19—H19B109.00
C7A—C17A—H17A110.00H19A—C19—H19B108.00
H17B—C17A—H17C109.00C19—C20—H20A110.00
H17A—C17A—H17B109.00C19—C20—H20B110.00
C13A—C18A—H18B109.00C19—C20—H20C110.00
C13A—C18A—H18C109.00H20A—C20—H20B109.00
C13A—C18A—H18A109.00H20A—C20—H20C109.00
H18A—C18A—H18C109.00H20B—C20—H20C109.00
H18B—C18A—H18C110.00
C3A—N1A—C2A—N2A0.2 (3)C12A—C11A—C16A—C15A0.2 (4)
C3A—N1A—C2A—C11A179.3 (2)C2A—C11A—C16A—C15A179.9 (3)
C2A—N1A—C3A—C1A0.9 (3)C11A—C12A—C13A—C18A178.2 (3)
C2A—N1A—C3A—C4A178.4 (2)C11A—C12A—C13A—C14A0.9 (5)
C2A—N2A—C1A—O1A180.0 (2)C12A—C13A—C14A—C15A0.3 (6)
C2A—N2A—C1A—C3A1.7 (3)C18A—C13A—C14A—C15A179.3 (4)
C1A—N2A—C2A—N1A1.2 (3)C13A—C14A—C15A—C16A1.4 (6)
C1A—N2A—C2A—C11A179.6 (2)C14A—C15A—C16A—C11A1.4 (6)
C2B—N1B—C3B—C1B1.5 (3)O1B—C1B—C3B—N1B179.6 (2)
C2B—N1B—C3B—C4B176.4 (3)O1B—C1B—C3B—C4B2.4 (4)
C3B—N1B—C2B—N2B1.5 (3)N2B—C1B—C3B—N1B0.9 (3)
C3B—N1B—C2B—C11B177.0 (2)N2B—C1B—C3B—C4B177.1 (2)
C1B—N2B—C2B—N1B1.0 (3)N1B—C2B—C11B—C12B172.8 (3)
C2B—N2B—C1B—O1B179.6 (2)N1B—C2B—C11B—C16B6.5 (4)
C2B—N2B—C1B—C3B0.0 (3)N2B—C2B—C11B—C12B5.6 (4)
C1B—N2B—C2B—C11B177.6 (2)N2B—C2B—C11B—C16B175.1 (3)
O1A—C1A—C3A—N1A179.8 (2)N1B—C3B—C4B—N3B178.8 (2)
O1A—C1A—C3A—C4A0.5 (4)N1B—C3B—C4B—C5B4.1 (4)
N2A—C1A—C3A—C4A177.7 (2)C1B—C3B—C4B—N3B1.2 (4)
N2A—C1A—C3A—N1A1.6 (3)C1B—C3B—C4B—C5B178.3 (2)
N1A—C2A—C11A—C12A178.1 (3)N3B—C4B—C5B—C6B47.2 (3)
N2A—C2A—C11A—C16A177.1 (3)N3B—C4B—C5B—C10B129.7 (3)
N1A—C2A—C11A—C16A2.0 (4)C3B—C4B—C5B—C6B130.0 (3)
N2A—C2A—C11A—C12A2.9 (4)C3B—C4B—C5B—C10B53.1 (4)
C1A—C3A—C4A—C5A175.5 (2)C4B—C5B—C6B—C7B177.6 (3)
N1A—C3A—C4A—N3A175.0 (2)C10B—C5B—C6B—C7B0.6 (4)
N1A—C3A—C4A—C5A3.7 (4)C4B—C5B—C10B—C9B176.7 (3)
C1A—C3A—C4A—N3A5.8 (4)C6B—C5B—C10B—C9B0.2 (4)
N3A—C4A—C5A—C10A140.5 (3)C5B—C6B—C7B—C8B0.6 (4)
C3A—C4A—C5A—C6A140.3 (3)C5B—C6B—C7B—C17B179.9 (3)
C3A—C4A—C5A—C10A40.7 (4)C6B—C7B—C8B—C9B0.2 (5)
N3A—C4A—C5A—C6A38.4 (3)C17B—C7B—C8B—C9B179.3 (4)
C4A—C5A—C6A—C7A178.8 (3)C7B—C8B—C9B—C10B1.0 (6)
C10A—C5A—C6A—C7A0.2 (4)C8B—C9B—C10B—C5B0.9 (5)
C6A—C5A—C10A—C9A1.3 (4)C2B—C11B—C12B—C13B177.8 (3)
C4A—C5A—C10A—C9A177.6 (3)C16B—C11B—C12B—C13B1.6 (4)
C5A—C6A—C7A—C8A1.0 (4)C2B—C11B—C16B—C15B177.2 (3)
C5A—C6A—C7A—C17A178.6 (3)C12B—C11B—C16B—C15B2.1 (4)
C6A—C7A—C8A—C9A1.0 (5)C11B—C12B—C13B—C14B0.4 (4)
C17A—C7A—C8A—C9A178.6 (3)C11B—C12B—C13B—C18B179.6 (3)
C7A—C8A—C9A—C10A0.2 (5)C12B—C13B—C14B—C15B1.8 (5)
C8A—C9A—C10A—C5A1.4 (5)C18B—C13B—C14B—C15B178.2 (3)
C2A—C11A—C12A—C13A179.0 (3)C13B—C14B—C15B—C16B1.2 (5)
C16A—C11A—C12A—C13A0.9 (4)C14B—C15B—C16B—C11B0.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3B—H3B1···O1B0.862.072.748 (3)135
O2—H2···N1B1.091.842.917 (3)170
N3B—H3B2···N1A0.862.373.033 (3)134
N2A—H2A···O1Ai0.861.952.803 (3)170
N2B—H2B···O1Bii0.861.972.805 (3)164
N3A—H3A1···O1A0.862.122.783 (3)134
N3A—H3A2···O2iii0.862.022.857 (3)163
C12A—H12A···O1Ai0.932.593.492 (4)164
C12B—H12B···O1Bii0.932.543.455 (3)168
C16B—H16B···O20.932.373.284 (4)168
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC18H17N3O·0.5C2H6O
Mr314.38
Crystal system, space groupTriclinic, P1
Temperature (K)300
a, b, c (Å)8.227 (4), 13.505 (7), 16.044 (8)
α, β, γ (°)87.451 (8), 78.869 (9), 80.241 (9)
V3)1723.6 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.23 × 0.22 × 0.21
Data collection
DiffractometerOxford Diffraction Xcalibur CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16691, 6512, 4294
Rint0.049
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.227, 1.02
No. of reflections6512
No. of parameters430
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.28

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3B—H3B1···O1B0.862.072.748 (3)135
O2—H2···N1B1.091.842.917 (3)170
N3B—H3B2···N1A0.862.373.033 (3)134
N2A—H2A···O1Ai0.861.952.803 (3)170
N2B—H2B···O1Bii0.861.972.805 (3)164
N3A—H3A1···O1A0.862.122.783 (3)134
N3A—H3A2···O2iii0.862.022.857 (3)163
C12A—H12A···O1Ai0.932.593.492 (4)164
C12B—H12B···O1Bii0.932.543.455 (3)168
C16B—H16B···O20.932.373.284 (4)168
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z; (iii) x1, y, z.
 

Acknowledgements

SMK thanks UGC–BRS and the University of Mysore for the award of a fellowship.

References

First citationChang, M.-J., Tsai, H.-Y., Fang, T.-C., Luo, M.-H. & Chen, K.-Y. (2012). Acta Cryst. E68, o902–o903.  CSD CrossRef IUCr Journals
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
First citationShafi, P. M., Sobha, T. D. & Basheer, P. A. M. (2005). Indian J. Chem. Sect. B, 44, 1298–1300.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShi, F., Zeng, X.-N., Wu, F.-Y., Yan, S., Zheng, W.-F. & Tu, S.-J. (2011). J. Heterocycl. Chem. 49, 59–63.  Web of Science CrossRef

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