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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(±)-1-(1-Allyl-1H-benzimidazol-2-yl)ethanol

aDepartment of Chemistry, Nanchang University, Nanchang 330031, People's Republic of China
*Correspondence e-mail: nculdp@126.com

(Received 17 October 2012; accepted 25 October 2012; online 3 November 2012)

The title compound, C12H14N2O, was obtained by reaction of (±)-1-(1H-benzimidazol-2-yl)ethanol with 3-bromo­prop-1-ene. The asymmetric unit contains four crystallographically independent mol­ecules. In the crystal, mol­ecules 1 and 2 are linked via O—H⋯N hydrogen bonds, forming chains propagating along [010]. Molecules 3 and 4 are linked to these chains via O—H⋯O hydrogen bonds.

Related literature

For background to the pharmaceutical properties and applications of benzimidazole derivatives, see: Garuti et al. (1999[Garuti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525-2530.]); Matsuno et al. (2000[Matsuno, T., Kato, M., Sasahara, H., Watanabe, T., Inaba, M., Takahashi, M., Yaguchi, S. I., Yoshioka, K., Sakato, M. & Kawashima, S. (2000). Chem. Pharm. Bull. 48, 1778-1781.]); Stibrany (2001[Stibrany, R. T. (2001). US Patent No. 6,180,788.]); Stibrany et al. (2002[Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142-o1144.]). For the synthesis of the title compound, see Xia & Xu (2008[Xia, R. & Xu, H.-J. (2008). Acta Cryst. E64, o1223.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14N2O

  • Mr = 202.25

  • Triclinic, P 1

  • a = 8.7816 (18) Å

  • b = 9.1233 (18) Å

  • c = 14.773 (3) Å

  • α = 96.66 (3)°

  • β = 107.15 (3)°

  • γ = 90.83 (3)°

  • V = 1121.8 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.24 × 0.22 × 0.15 mm

Data collection
  • Rigaku Mercury2 (2x2 bin mode) diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.982, Tmax = 0.988

  • 10277 measured reflections

  • 8368 independent reflections

  • 4897 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.128

  • S = 1.02

  • 4404 reflections

  • 541 parameters

  • 3 restraints

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1B⋯N3i 0.82 1.99 2.801 (4) 167
O2—H2B⋯N1ii 0.82 2.05 2.811 (4) 155
O3—H3B⋯O1iii 0.82 1.99 2.808 (4) 175
O4—H4B⋯O2i 0.82 1.97 2.787 (4) 176
Symmetry codes: (i) x+1, y, z; (ii) x-1, y+1, z; (iii) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Benzimidazole and its derivatives are important pharmaceutical intermediates and have attracted considerable attention because of good biological and pharmaceutical activities (Matsuno, et al., 2000; Garuti, et al., 1999). These compounds also display other interesting properties as catalysts (Stibrany, 2001) and proton sponges (Stibrany et al., 2002). In this paper, the synthesis and crystal structure of the title compound is reported.

Fig. 1 shows an ORTEP plot of the title compound. There are four crystallographically independent molecules in the asymmetric unit. The CC bonds are within normal ranges. The four benzimidazole ring systems are substantially planar with the the largest deviations from the mean plane of 0.018 (5), 0.008 (5), 0.018 (5) and 0.017 (5) Å for C1–C7/N1/N2, C13–C19/N3/N4, C25–C31/N5/N6 and C37–C43/N7/N8, respectively. In the structure of the title compound (Fig. 2), molecules are connected through intermolecular O—H···N and O—H···O hydrogen bonds into layers parallel to the (110) plane.

Related literature top

For background to the pharmaceutical properties and applications of benzimidazole derivatives, see: Garuti et al. (1999); Matsuno et al. (2000); Stibrany (2001); Stibrany et al. (2002). For the synthesis of the title compound, see Xia & Xu (2008).

Experimental top

All chemicals were obtained from commercial sources and used directly without further purification. (+/-)-1-(1H-benzimidazol-2-yl)ethanol was synthesized according to the literature methos (Xia & Xu, 2008). (+/-)-1-(1H-benzimidazol-2-yl)ethanol (0.81 g, 5 mmol) was dissolved in acetone (10 ml), then 3-bromoprop-1-ene (0.6 g, 5 mmol) and K2CO3 (0.83 g, 6 mmol) was added to the solution. The mixture was heated to reflux for 15 h at 70°C. The organic solvent was removed under reduced pressure, and 50 ml chloroform was added. The solid was removed by filtration and washed with chloroform. The combined organic solution was washed with water, dried over anhydrous Na2SO4, and the solvent removed under reduced pressure. The residues was purified by choromatography column with CHCl3 to afford the pure light yellow solid (0.745 g, yield: 74%). 1H-NMR(CDCl3, 500 MHz): δ1.69 (d, 3 H), 3.66(br, 1H), 4.80(m, 2H), 4.98(d, 1H), 5.11 (q, 1 H), 5.21(d, 1 H), 5.94(m, 1 H), 7.25(m, 3H), 7.73 (m, 1 H). Single crystals of the title compound suitable for X-ray diffraction analysis were obtained from a methanol solution by slow evaporation after a week.

Refinement top

All H atoms attached to C and O atom were fixed geometrically and treated as riding, with C—H = 0.98 Å (methine), 0.96 Å (methyl) or 0.93 Å(aromatic), O—H = 0.82 Å, and with Uiso (H) = 1.2Ueq (C) or 1.5Ueq(C, O) for methyl and hydroxy H atoms. In the absence of significant anomalous scattering, 3937 Friedel pairs have been merged.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity. For clarity purposes, molecules with atoms labelled with suffix A have been generated by the symmetry operation x, y + 1, z.
[Figure 2] Fig. 2. Partial crystal packing of the title compound showing the hydrogen bonding network (dashed lines). H atoms not involved in hydrogen bonding are omitted for clarity.
(±)-1-(1-Allyl-1H-benzimidazol-2-yl)ethanol top
Crystal data top
C12H14N2OV = 1121.8 (4) Å3
Mr = 202.25Z = 4
Triclinic, P1F(000) = 432
Hall symbol: P 1Dx = 1.198 Mg m3
a = 8.7816 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1233 (18) Åθ = 2.4–28.0°
c = 14.773 (3) ŵ = 0.08 mm1
α = 96.66 (3)°T = 293 K
β = 107.15 (3)°Block, colourless
γ = 90.83 (3)°0.24 × 0.22 × 0.15 mm
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer
8368 independent reflections
Radiation source: fine-focus sealed tube4897 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 2.4°
ω scansh = 1010
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1111
Tmin = 0.982, Tmax = 0.988l = 1818
10277 measured 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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0586P)2]
where P = (Fo2 + 2Fc2)/3
4404 reflections(Δ/σ)max < 0.001
541 parametersΔρmax = 0.16 e Å3
3 restraintsΔρmin = 0.19 e Å3
Crystal data top
C12H14N2Oγ = 90.83 (3)°
Mr = 202.25V = 1121.8 (4) Å3
Triclinic, P1Z = 4
a = 8.7816 (18) ÅMo Kα radiation
b = 9.1233 (18) ŵ = 0.08 mm1
c = 14.773 (3) ÅT = 293 K
α = 96.66 (3)°0.24 × 0.22 × 0.15 mm
β = 107.15 (3)°
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer
8368 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
4897 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.988Rint = 0.031
10277 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0553 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
4404 reflectionsΔρmin = 0.19 e Å3
541 parameters
Special details top

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
C10.5685 (5)0.0013 (4)0.2505 (3)0.0458 (10)
C20.5232 (6)0.1444 (5)0.2097 (3)0.0582 (12)
H2A0.54540.22220.24630.070*
C30.4441 (6)0.1693 (6)0.1128 (4)0.0690 (14)
H3A0.41350.26540.08350.083*
C40.4100 (6)0.0526 (6)0.0590 (3)0.0712 (14)
H4A0.35580.07310.00580.085*
C50.4531 (6)0.0936 (6)0.0974 (3)0.0643 (13)
H5A0.43100.17080.06030.077*
C60.5318 (5)0.1171 (5)0.1951 (3)0.0489 (10)
C70.6574 (4)0.2036 (4)0.3452 (3)0.0435 (10)
C80.7359 (5)0.3134 (4)0.4309 (3)0.0479 (10)
H8A0.66970.39900.43070.058*
C90.7615 (6)0.2491 (5)0.5242 (3)0.0594 (12)
H9A0.81180.32330.57670.089*
H9B0.82840.16670.52540.089*
H9C0.66040.21670.52960.089*
C100.5846 (5)0.3949 (5)0.2284 (3)0.0556 (12)
H10A0.60170.46730.28440.067*
H10B0.48050.40840.18480.067*
C110.7095 (7)0.4188 (5)0.1814 (4)0.0688 (13)
H11A0.81460.40420.21500.083*
C120.6823 (9)0.4589 (7)0.0964 (5)0.104 (2)
H12A0.57860.47450.06070.125*
H12B0.76650.47190.07150.125*
C130.1628 (5)0.7216 (5)0.6969 (3)0.0472 (10)
C140.2453 (5)0.7395 (6)0.7940 (3)0.0627 (13)
H14A0.27190.83270.82890.075*
C150.2858 (6)0.6124 (6)0.8360 (3)0.0683 (14)
H15A0.34210.62020.90060.082*
C160.2449 (6)0.4733 (6)0.7843 (4)0.0662 (13)
H16A0.27420.39000.81500.079*
C170.1610 (5)0.4556 (5)0.6878 (3)0.0560 (12)
H17A0.13380.36200.65340.067*
C180.1189 (5)0.5824 (4)0.6439 (3)0.0445 (10)
C190.0315 (4)0.7439 (4)0.5469 (3)0.0428 (10)
C200.0486 (5)0.8173 (4)0.4616 (3)0.0478 (10)
H20A0.01860.90280.45960.057*
C210.0795 (6)0.7139 (5)0.3688 (3)0.0610 (12)
H21A0.13110.76560.31600.091*
H21B0.14690.63070.36990.091*
H21C0.02010.68000.36210.091*
C220.1121 (5)0.9846 (4)0.6599 (4)0.0564 (12)
H22A0.09531.03340.60300.068*
H22B0.21691.01690.70290.068*
C230.0127 (6)1.0274 (5)0.7075 (4)0.0688 (14)
H23A0.11901.00310.67330.083*
C240.0180 (9)1.0959 (7)0.7930 (5)0.106 (2)
H24A0.12301.12180.82900.127*
H24B0.06491.11940.81840.127*
C250.1235 (5)0.2875 (5)0.1527 (3)0.0510 (11)
C260.0739 (6)0.2591 (5)0.0539 (3)0.0646 (13)
H26A0.04750.16390.02200.077*
C270.0664 (7)0.3815 (6)0.0058 (4)0.0737 (14)
H27A0.03360.36790.06060.088*
C280.1059 (6)0.5232 (5)0.0528 (4)0.0726 (15)
H28A0.09920.60200.01730.087*
C290.1547 (6)0.5505 (5)0.1507 (4)0.0672 (13)
H29A0.18030.64620.18200.081*
C300.1644 (5)0.4289 (5)0.2017 (3)0.0525 (11)
C310.2025 (5)0.2829 (4)0.3089 (3)0.0466 (10)
C320.2450 (5)0.2198 (5)0.4023 (3)0.0508 (10)
H32A0.32550.14700.40080.061*
C330.3171 (6)0.3359 (5)0.4866 (3)0.0616 (12)
H33A0.34220.29090.54450.092*
H33B0.24210.41080.48870.092*
H33C0.41270.37980.48010.092*
C340.1221 (6)0.0331 (4)0.2065 (4)0.0594 (12)
H34A0.17570.00820.26450.071*
H34B0.16810.00670.15720.071*
C350.0505 (6)0.0127 (5)0.1766 (4)0.0705 (14)
H35A0.11100.02780.21450.085*
C360.1226 (8)0.1036 (6)0.1027 (5)0.0980 (19)
H36A0.06620.14650.06300.118*
H36B0.23120.12670.08890.118*
C370.5376 (5)1.0456 (5)0.6951 (3)0.0533 (11)
C380.5520 (6)1.1886 (6)0.7412 (4)0.0732 (15)
H38A0.52711.26900.70720.088*
C390.6052 (7)1.2070 (6)0.8401 (4)0.0818 (16)
H39A0.61491.30160.87290.098*
C400.6444 (7)1.0866 (7)0.8916 (4)0.0816 (16)
H40A0.68031.10320.95790.098*
C410.6314 (6)0.9450 (6)0.8468 (4)0.0728 (14)
H41A0.65710.86500.88120.087*
C420.5785 (5)0.9265 (5)0.7483 (3)0.0562 (12)
C430.4930 (5)0.8496 (5)0.5936 (3)0.0512 (11)
C440.4472 (5)0.7419 (5)0.5029 (3)0.0537 (11)
H44A0.36700.67030.50840.064*
C450.3721 (6)0.8175 (5)0.4162 (3)0.0629 (12)
H45A0.34470.74590.36020.094*
H45B0.44630.89150.41040.094*
H45C0.27740.86310.42280.094*
C460.5790 (6)0.6494 (5)0.7029 (4)0.0667 (14)
H46A0.52060.58080.64800.080*
H46B0.54040.63200.75610.080*
C470.7517 (7)0.6209 (6)0.7272 (4)0.0810 (16)
H47A0.80370.63500.68210.097*
C480.8330 (9)0.5788 (9)0.8051 (5)0.121 (3)
H48A0.78470.56370.85170.146*
H48B0.94090.56300.81570.146*
N10.6487 (4)0.0580 (4)0.3448 (2)0.0471 (8)
N20.5884 (4)0.2455 (3)0.2568 (2)0.0468 (8)
N30.0372 (4)0.5997 (4)0.5496 (2)0.0470 (8)
N40.1055 (4)0.8238 (4)0.6335 (2)0.0456 (8)
N50.2142 (4)0.4240 (4)0.3004 (3)0.0535 (9)
N60.1496 (4)0.1939 (4)0.2233 (3)0.0515 (9)
N70.4845 (4)0.9947 (4)0.5973 (3)0.0573 (10)
N80.5482 (4)0.8010 (4)0.6817 (3)0.0547 (9)
O10.8842 (3)0.3584 (3)0.4171 (2)0.0575 (8)
H1B0.92300.42340.46170.069*
O20.1956 (3)0.8682 (3)0.4758 (2)0.0577 (8)
H2B0.21180.93110.43920.069*
O30.1079 (4)0.1432 (3)0.4119 (2)0.0636 (8)
H3B0.03890.20200.41390.095*
O40.5825 (4)0.6616 (3)0.4948 (2)0.0656 (9)
H4B0.65090.71860.48890.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.044 (2)0.043 (2)0.048 (2)0.0030 (18)0.010 (2)0.0025 (19)
C20.063 (3)0.047 (3)0.061 (3)0.004 (2)0.017 (3)0.003 (2)
C30.073 (3)0.062 (3)0.067 (3)0.014 (3)0.022 (3)0.014 (3)
C40.072 (3)0.084 (4)0.047 (3)0.010 (3)0.009 (3)0.011 (3)
C50.062 (3)0.074 (3)0.053 (3)0.002 (3)0.011 (2)0.007 (3)
C60.037 (2)0.052 (3)0.057 (3)0.0002 (19)0.012 (2)0.006 (2)
C70.036 (2)0.043 (2)0.051 (3)0.0041 (18)0.013 (2)0.002 (2)
C80.041 (2)0.043 (2)0.058 (3)0.0033 (18)0.014 (2)0.0006 (19)
C90.069 (3)0.059 (3)0.048 (3)0.004 (2)0.016 (2)0.004 (2)
C100.054 (3)0.047 (3)0.069 (3)0.007 (2)0.017 (2)0.019 (2)
C110.074 (3)0.054 (3)0.084 (4)0.005 (2)0.030 (3)0.016 (3)
C120.133 (6)0.095 (5)0.102 (5)0.005 (4)0.056 (4)0.032 (4)
C130.043 (2)0.049 (2)0.051 (3)0.0064 (19)0.017 (2)0.005 (2)
C140.056 (3)0.070 (3)0.053 (3)0.002 (3)0.007 (2)0.004 (2)
C150.066 (3)0.086 (4)0.049 (3)0.005 (3)0.012 (3)0.008 (3)
C160.063 (3)0.075 (3)0.064 (3)0.015 (3)0.016 (3)0.025 (3)
C170.054 (3)0.055 (3)0.061 (3)0.009 (2)0.017 (2)0.015 (2)
C180.041 (2)0.045 (2)0.048 (2)0.0037 (18)0.015 (2)0.0018 (19)
C190.033 (2)0.043 (2)0.052 (3)0.0012 (17)0.014 (2)0.0045 (19)
C200.048 (2)0.040 (2)0.056 (3)0.0050 (19)0.016 (2)0.0061 (19)
C210.077 (3)0.055 (3)0.052 (3)0.005 (2)0.019 (2)0.009 (2)
C220.059 (3)0.038 (2)0.069 (3)0.001 (2)0.018 (2)0.002 (2)
C230.072 (3)0.052 (3)0.083 (4)0.008 (2)0.030 (3)0.007 (3)
C240.123 (6)0.095 (5)0.106 (5)0.005 (4)0.057 (4)0.020 (4)
C250.049 (2)0.047 (2)0.062 (3)0.011 (2)0.022 (2)0.011 (2)
C260.081 (4)0.057 (3)0.056 (3)0.009 (3)0.020 (3)0.008 (2)
C270.085 (4)0.077 (4)0.060 (3)0.013 (3)0.019 (3)0.018 (3)
C280.089 (4)0.063 (3)0.067 (3)0.003 (3)0.019 (3)0.024 (3)
C290.075 (3)0.051 (3)0.076 (4)0.001 (2)0.021 (3)0.013 (2)
C300.051 (3)0.049 (3)0.058 (3)0.001 (2)0.017 (2)0.010 (2)
C310.041 (2)0.047 (2)0.054 (3)0.0046 (19)0.016 (2)0.006 (2)
C320.047 (2)0.044 (2)0.067 (3)0.0087 (19)0.022 (2)0.016 (2)
C330.058 (3)0.063 (3)0.058 (3)0.005 (2)0.010 (2)0.006 (2)
C340.065 (3)0.039 (2)0.074 (3)0.006 (2)0.020 (3)0.005 (2)
C350.072 (3)0.056 (3)0.089 (4)0.005 (3)0.033 (3)0.010 (3)
C360.085 (4)0.088 (4)0.108 (5)0.008 (4)0.010 (4)0.009 (4)
C370.044 (2)0.058 (3)0.061 (3)0.009 (2)0.019 (2)0.010 (2)
C380.078 (4)0.059 (3)0.076 (4)0.009 (3)0.015 (3)0.005 (3)
C390.086 (4)0.072 (4)0.082 (4)0.007 (3)0.026 (3)0.011 (3)
C400.079 (4)0.107 (5)0.060 (3)0.006 (3)0.025 (3)0.007 (3)
C410.074 (4)0.080 (4)0.068 (3)0.009 (3)0.021 (3)0.019 (3)
C420.048 (3)0.065 (3)0.061 (3)0.007 (2)0.021 (2)0.017 (2)
C430.042 (2)0.047 (3)0.067 (3)0.003 (2)0.017 (2)0.013 (2)
C440.045 (3)0.045 (2)0.073 (3)0.000 (2)0.021 (2)0.008 (2)
C450.055 (3)0.060 (3)0.069 (3)0.002 (2)0.013 (2)0.002 (2)
C460.066 (3)0.055 (3)0.085 (4)0.008 (2)0.024 (3)0.028 (3)
C470.075 (4)0.075 (4)0.107 (4)0.026 (3)0.035 (3)0.043 (3)
C480.093 (5)0.158 (7)0.129 (6)0.038 (5)0.034 (5)0.076 (5)
N10.049 (2)0.0373 (19)0.053 (2)0.0011 (16)0.0136 (18)0.0013 (16)
N20.045 (2)0.0405 (19)0.052 (2)0.0014 (15)0.0100 (17)0.0063 (16)
N30.045 (2)0.043 (2)0.052 (2)0.0017 (16)0.0121 (17)0.0070 (16)
N40.045 (2)0.0398 (19)0.050 (2)0.0014 (15)0.0148 (17)0.0013 (16)
N50.056 (2)0.047 (2)0.060 (2)0.0061 (17)0.0182 (19)0.0114 (17)
N60.052 (2)0.042 (2)0.061 (2)0.0063 (16)0.0168 (19)0.0099 (18)
N70.060 (2)0.047 (2)0.064 (3)0.0065 (18)0.016 (2)0.0099 (18)
N80.053 (2)0.051 (2)0.065 (3)0.0076 (18)0.021 (2)0.0155 (19)
O10.0543 (18)0.0485 (17)0.0662 (19)0.0111 (14)0.0192 (15)0.0076 (14)
O20.0560 (18)0.0567 (18)0.0671 (19)0.0160 (14)0.0230 (15)0.0213 (15)
O30.0650 (19)0.0506 (17)0.083 (2)0.0016 (15)0.0296 (17)0.0195 (16)
O40.0586 (19)0.0491 (17)0.092 (2)0.0072 (15)0.0274 (18)0.0055 (16)
Geometric parameters (Å, º) top
C1—C61.394 (6)C25—N61.393 (5)
C1—C21.395 (6)C26—C271.384 (7)
C1—N11.396 (5)C26—H26A0.9300
C2—C31.385 (7)C27—C281.383 (7)
C2—H2A0.9300C27—H27A0.9300
C3—C41.385 (7)C28—C291.373 (7)
C3—H3A0.9300C28—H28A0.9300
C4—C51.388 (7)C29—C301.402 (6)
C4—H4A0.9300C29—H29A0.9300
C5—C61.394 (6)C30—N51.399 (6)
C5—H5A0.9300C31—N51.314 (5)
C6—N21.385 (5)C31—N61.371 (5)
C7—N11.329 (5)C31—C321.505 (6)
C7—N21.369 (5)C32—O31.434 (5)
C7—C81.501 (6)C32—C331.510 (6)
C8—O11.438 (5)C32—H32A0.9800
C8—C91.517 (6)C33—H33A0.9600
C8—H8A0.9800C33—H33B0.9600
C9—H9A0.9600C33—H33C0.9600
C9—H9B0.9600C34—N61.463 (5)
C9—H9C0.9600C34—C351.486 (7)
C10—N21.470 (5)C34—H34A0.9700
C10—C111.487 (7)C34—H34B0.9700
C10—H10A0.9700C35—C361.284 (7)
C10—H10B0.9700C35—H35A0.9300
C11—C121.303 (8)C36—H36A0.9300
C11—H11A0.9300C36—H36B0.9300
C12—H12A0.9300C37—C381.386 (6)
C12—H12B0.9300C37—N71.400 (6)
C13—N41.392 (5)C37—C421.404 (6)
C13—C141.392 (6)C38—C391.384 (7)
C13—C181.397 (5)C38—H38A0.9300
C14—C151.380 (7)C39—C401.398 (8)
C14—H14A0.9300C39—H39A0.9300
C15—C161.387 (7)C40—C411.368 (8)
C15—H15A0.9300C40—H40A0.9300
C16—C171.388 (7)C41—C421.379 (7)
C16—H16A0.9300C41—H41A0.9300
C17—C181.393 (6)C42—N81.388 (6)
C17—H17A0.9300C43—N71.323 (5)
C18—N31.395 (5)C43—N81.376 (5)
C19—N31.322 (5)C43—C441.512 (6)
C19—N41.368 (5)C44—O41.432 (5)
C19—C201.489 (6)C44—C451.508 (6)
C20—O21.443 (5)C44—H44A0.9800
C20—C211.522 (6)C45—H45A0.9600
C20—H20A0.9800C45—H45B0.9600
C21—H21A0.9600C45—H45C0.9600
C21—H21B0.9600C46—N81.466 (5)
C21—H21C0.9600C46—C471.487 (7)
C22—N41.469 (5)C46—H46A0.9700
C22—C231.501 (6)C46—H46B0.9700
C22—H22A0.9700C47—C481.268 (8)
C22—H22B0.9700C47—H47A0.9300
C23—C241.292 (7)C48—H48A0.9300
C23—H23A0.9300C48—H48B0.9300
C24—H24A0.9300O1—H1B0.8201
C24—H24B0.9300O2—H2B0.8197
C25—C261.386 (6)O3—H3B0.8200
C25—C301.391 (6)O4—H4B0.8200
C6—C1—C2120.6 (4)C29—C28—H28A119.2
C6—C1—N1109.5 (3)C27—C28—H28A119.2
C2—C1—N1130.0 (4)C28—C29—C30117.5 (4)
C3—C2—C1117.7 (4)C28—C29—H29A121.2
C3—C2—H2A121.2C30—C29—H29A121.2
C1—C2—H2A121.2C25—C30—N5110.6 (4)
C2—C3—C4120.7 (4)C25—C30—C29119.8 (4)
C2—C3—H3A119.6N5—C30—C29129.6 (4)
C4—C3—H3A119.6N5—C31—N6113.8 (4)
C3—C4—C5123.0 (5)N5—C31—C32124.7 (4)
C3—C4—H4A118.5N6—C31—C32121.5 (3)
C5—C4—H4A118.5O3—C32—C31110.0 (3)
C4—C5—C6115.7 (5)O3—C32—C33111.8 (4)
C4—C5—H5A122.2C31—C32—C33112.3 (4)
C6—C5—H5A122.2O3—C32—H32A107.5
N2—C6—C5131.6 (4)C31—C32—H32A107.5
N2—C6—C1106.1 (4)C33—C32—H32A107.5
C5—C6—C1122.3 (4)C32—C33—H33A109.5
N1—C7—N2112.5 (3)C32—C33—H33B109.5
N1—C7—C8125.2 (4)H33A—C33—H33B109.5
N2—C7—C8122.3 (4)C32—C33—H33C109.5
O1—C8—C7104.7 (3)H33A—C33—H33C109.5
O1—C8—C9111.9 (3)H33B—C33—H33C109.5
C7—C8—C9112.7 (3)N6—C34—C35112.3 (4)
O1—C8—H8A109.2N6—C34—H34A109.1
C7—C8—H8A109.2C35—C34—H34A109.1
C9—C8—H8A109.2N6—C34—H34B109.1
C8—C9—H9A109.5C35—C34—H34B109.1
C8—C9—H9B109.5H34A—C34—H34B107.9
H9A—C9—H9B109.5C36—C35—C34125.2 (5)
C8—C9—H9C109.5C36—C35—H35A117.4
H9A—C9—H9C109.5C34—C35—H35A117.4
H9B—C9—H9C109.5C35—C36—H36A120.0
N2—C10—C11110.9 (4)C35—C36—H36B120.0
N2—C10—H10A109.5H36A—C36—H36B120.0
C11—C10—H10A109.5C38—C37—N7129.6 (4)
N2—C10—H10B109.5C38—C37—C42120.1 (5)
C11—C10—H10B109.5N7—C37—C42110.3 (4)
H10A—C10—H10B108.0C39—C38—C37117.4 (5)
C12—C11—C10124.7 (6)C39—C38—H38A121.3
C12—C11—H11A117.7C37—C38—H38A121.3
C10—C11—H11A117.7C38—C39—C40121.5 (5)
C11—C12—H12A120.0C38—C39—H39A119.2
C11—C12—H12B120.0C40—C39—H39A119.2
H12A—C12—H12B120.0C41—C40—C39121.6 (5)
N4—C13—C14131.7 (4)C41—C40—H40A119.2
N4—C13—C18106.0 (4)C39—C40—H40A119.2
C14—C13—C18122.3 (4)C40—C41—C42116.9 (5)
C15—C14—C13116.8 (4)C40—C41—H41A121.5
C15—C14—H14A121.6C42—C41—H41A121.5
C13—C14—H14A121.6C41—C42—N8132.0 (5)
C14—C15—C16121.7 (5)C41—C42—C37122.5 (5)
C14—C15—H15A119.1N8—C42—C37105.5 (4)
C16—C15—H15A119.1N7—C43—N8113.9 (4)
C15—C16—C17121.4 (5)N7—C43—C44125.1 (4)
C15—C16—H16A119.3N8—C43—C44121.0 (4)
C17—C16—H16A119.3O4—C44—C45112.6 (4)
C16—C17—C18117.9 (4)O4—C44—C43110.1 (3)
C16—C17—H17A121.1C45—C44—C43111.8 (4)
C18—C17—H17A121.1O4—C44—H44A107.4
C17—C18—N3131.0 (4)C45—C44—H44A107.4
C17—C18—C13119.9 (4)C43—C44—H44A107.4
N3—C18—C13109.2 (4)C44—C45—H45A109.5
N3—C19—N4112.8 (4)C44—C45—H45B109.5
N3—C19—C20125.7 (4)H45A—C45—H45B109.5
N4—C19—C20121.5 (4)C44—C45—H45C109.5
O2—C20—C19105.9 (3)H45A—C45—H45C109.5
O2—C20—C21111.4 (4)H45B—C45—H45C109.5
C19—C20—C21112.3 (3)N8—C46—C47111.8 (4)
O2—C20—H20A109.0N8—C46—H46A109.3
C19—C20—H20A109.0C47—C46—H46A109.3
C21—C20—H20A109.0N8—C46—H46B109.3
C20—C21—H21A109.5C47—C46—H46B109.3
C20—C21—H21B109.5H46A—C46—H46B107.9
H21A—C21—H21B109.5C48—C47—C46124.4 (6)
C20—C21—H21C109.5C48—C47—H47A117.8
H21A—C21—H21C109.5C46—C47—H47A117.8
H21B—C21—H21C109.5C47—C48—H48A120.0
N4—C22—C23110.8 (3)C47—C48—H48B120.0
N4—C22—H22A109.5H48A—C48—H48B120.0
C23—C22—H22A109.5C7—N1—C1105.2 (4)
N4—C22—H22B109.5C7—N2—C6106.7 (3)
C23—C22—H22B109.5C7—N2—C10128.0 (4)
H22A—C22—H22B108.1C6—N2—C10125.2 (4)
C24—C23—C22124.2 (6)C19—N3—C18105.6 (3)
C24—C23—H23A117.9C19—N4—C13106.4 (3)
C22—C23—H23A117.9C19—N4—C22128.3 (4)
C23—C24—H24A120.0C13—N4—C22125.1 (4)
C23—C24—H24B120.0C31—N5—C30104.2 (4)
H24A—C24—H24B120.0C31—N6—C25106.2 (3)
C26—C25—C30123.1 (4)C31—N6—C34128.3 (4)
C26—C25—N6131.7 (4)C25—N6—C34125.5 (4)
C30—C25—N6105.2 (4)C43—N7—C37104.1 (4)
C27—C26—C25115.7 (5)C43—N8—C42106.2 (3)
C27—C26—H26A122.2C43—N8—C46128.0 (4)
C25—C26—H26A122.2C42—N8—C46125.7 (4)
C28—C27—C26122.4 (5)C8—O1—H1B104.2
C28—C27—H27A118.8C20—O2—H2B98.1
C26—C27—H27A118.8C32—O3—H3B109.5
C29—C28—C27121.6 (5)C44—O4—H4B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···N3i0.821.992.801 (4)167
O2—H2B···N1ii0.822.052.811 (4)155
O3—H3B···O1iii0.821.992.808 (4)175
O4—H4B···O2i0.821.972.787 (4)176
Symmetry codes: (i) x+1, y, z; (ii) x1, y+1, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC12H14N2O
Mr202.25
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.7816 (18), 9.1233 (18), 14.773 (3)
α, β, γ (°)96.66 (3), 107.15 (3), 90.83 (3)
V3)1121.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.24 × 0.22 × 0.15
Data collection
DiffractometerRigaku Mercury2 (2x2 bin mode)
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.982, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
10277, 8368, 4897
Rint0.031
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.128, 1.02
No. of reflections4404
No. of parameters541
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.19

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···N3i0.821.992.801 (4)167.4
O2—H2B···N1ii0.822.052.811 (4)154.7
O3—H3B···O1iii0.821.992.808 (4)174.9
O4—H4B···O2i0.821.972.787 (4)175.6
Symmetry codes: (i) x+1, y, z; (ii) x1, y+1, z; (iii) x1, y, z.
 

References

First citationGaruti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525–2530.  Web of Science CrossRef PubMed CAS
First citationMatsuno, T., Kato, M., Sasahara, H., Watanabe, T., Inaba, M., Takahashi, M., Yaguchi, S. I., Yoshioka, K., Sakato, M. & Kawashima, S. (2000). Chem. Pharm. Bull. 48, 1778–1781.  CrossRef PubMed CAS
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationStibrany, R. T. (2001). US Patent No. 6,180,788.
First citationStibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142–o1144.  Web of Science CSD CrossRef CAS IUCr Journals
First citationXia, R. & Xu, H.-J. (2008). Acta Cryst. E64, o1223.  Web of Science CSD CrossRef IUCr Journals

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