Literature DB >> 21588036

1,3,3-Trimethyl-1,2,3,4-tetra-hydro-pyrido[1,2-a]benzimidazol-1-ol.

Sayed Hasan Mehdi, Rokiah Hashim, Raza Murad Ghalib, Chin Sing Yeap, Hoong-Kun Fun.   

Abstract

In the title compound, C(14)H(18)N(2)O, the benzimidazole grouping is close to planar, with a maximum deviation of 0.042 Å; the six-membered non-aromatic ring adopts an envelope conformation. In the crystal structure, mol-ecules are linked into infinite sheets lying parallel to the bc plane by O-H⋯N and C-H⋯O hydrogen bonds.

Entities:  

Year:  2010        PMID： 21588036      PMCID： PMC3006987          DOI： 10.1107/S1600536810024487

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For applications of benzimidazole derivatives, see: Horton et al. (2003 ▶); Insuasty et al. (2008a ▶,b ▶). For the preparation of the title compound, see: Grech et al. (1994 ▶). For ring conformations, see Cremer & Pople (1975 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H18N2O M = 230.30 Monoclinic, a = 9.615 (5) Å b = 8.194 (4) Å c = 15.965 (8) Å β = 99.601 (12)° V = 1240.2 (11) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 100 K 0.38 × 0.12 × 0.07 mm

Data collection

Bruker APEXII DUO CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.995 13460 measured reflections 3597 independent reflections 2612 reflections with I > 2σ(I) R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.117 S = 1.02 3597 reflections 226 parameters All H-atom parameters refined Δρmax = 0.33 e Å−3 Δρmin = −0.25 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024487/hb5508sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024487/hb5508Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H18N2OF(000) = 496
Mr = 230.30Dx = 1.233 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2162 reflections
a = 9.615 (5) Åθ = 3.1–29.6°
b = 8.194 (4) ŵ = 0.08 mm−1
c = 15.965 (8) ÅT = 100 K
β = 99.601 (12)°Needle, yellow
V = 1240.2 (11) Å30.38 × 0.12 × 0.07 mm
Z = 4
Bruker APEXII DUO CCD diffractometer3597 independent reflections
Radiation source: fine-focus sealed tube2612 reflections with I > 2σ(I)
graphiteRint = 0.052
φ and ω scansθmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.971, Tmax = 0.995k = −11→10
13460 measured reflectionsl = −22→18
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) = 0.117All H-atom parameters refined
S = 1.02w = 1/[σ2(Fo2) + (0.0528P)2 + 0.2357P] where P = (Fo2 + 2Fc2)/3
3597 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
O10.65445 (9)0.44319 (11)0.12156 (6)0.0178 (2)
N10.40305 (10)0.05504 (14)0.22183 (7)0.0176 (2)
N20.54560 (10)0.19700 (13)0.15038 (6)0.0148 (2)
C10.32424 (12)0.11377 (16)0.14618 (8)0.0160 (3)
C20.17999 (13)0.09810 (17)0.11474 (9)0.0199 (3)
C30.12707 (13)0.17745 (18)0.03945 (9)0.0215 (3)
C40.21420 (13)0.27314 (18)−0.00320 (8)0.0199 (3)
C50.35783 (13)0.28830 (17)0.02639 (8)0.0179 (3)
C60.41136 (12)0.20479 (15)0.10110 (8)0.0152 (2)
C70.67647 (12)0.27365 (16)0.13019 (8)0.0153 (3)
C80.79944 (12)0.23815 (16)0.20337 (8)0.0164 (3)
C90.79390 (12)0.07980 (16)0.25468 (8)0.0165 (3)
C100.65512 (13)0.08393 (18)0.29055 (8)0.0186 (3)
C110.53240 (12)0.10891 (16)0.22157 (8)0.0157 (3)
C120.70543 (14)0.21133 (19)0.04460 (9)0.0208 (3)
C130.80018 (14)−0.07437 (18)0.20160 (9)0.0218 (3)
C140.91813 (13)0.08019 (19)0.32872 (9)0.0224 (3)
H1A0.0269 (15)0.1672 (18)0.0155 (9)0.020 (4)*
H2A0.1203 (16)0.033 (2)0.1467 (10)0.026 (4)*
H4A0.1727 (15)0.3345 (18)−0.0553 (9)0.016 (4)*
H5A0.4140 (15)0.3569 (19)−0.0037 (9)0.017 (4)*
H8A0.8923 (16)0.241 (2)0.1794 (10)0.025 (4)*
H8B0.8028 (15)0.334 (2)0.2438 (10)0.025 (4)*
H10A0.6384 (15)−0.0185 (19)0.3209 (9)0.018 (4)*
H10B0.6583 (16)0.177 (2)0.3319 (10)0.024 (4)*
H12A0.7260 (17)0.095 (2)0.0457 (11)0.030 (4)*
H12B0.7853 (17)0.279 (2)0.0300 (11)0.032 (4)*
H12C0.6228 (18)0.233 (2)−0.0008 (11)0.034 (5)*
H13A0.7168 (16)−0.0878 (19)0.1571 (10)0.024 (4)*
H13B0.8059 (15)−0.171 (2)0.2371 (10)0.024 (4)*
H13C0.8856 (17)−0.074 (2)0.1725 (11)0.032 (4)*
H14A0.9187 (16)0.180 (2)0.3648 (10)0.028 (4)*
H14B0.9107 (17)−0.017 (2)0.3658 (11)0.034 (5)*
H14C1.0108 (18)0.082 (2)0.3068 (11)0.036 (5)*
H1O10.640 (2)0.487 (3)0.1756 (13)0.050 (6)*
U11U22U33U12U13U23
O10.0215 (4)0.0149 (5)0.0175 (5)0.0005 (3)0.0047 (3)0.0024 (4)
N10.0167 (5)0.0195 (6)0.0166 (5)−0.0010 (4)0.0028 (4)0.0018 (4)
N20.0138 (4)0.0170 (5)0.0130 (5)−0.0010 (4)0.0009 (4)0.0014 (4)
C10.0169 (5)0.0153 (6)0.0158 (6)0.0004 (4)0.0024 (4)−0.0007 (5)
C20.0155 (5)0.0206 (7)0.0232 (7)−0.0010 (5)0.0020 (5)−0.0017 (6)
C30.0171 (6)0.0229 (7)0.0229 (7)0.0009 (5)−0.0014 (5)−0.0041 (6)
C40.0208 (6)0.0210 (7)0.0164 (6)0.0036 (5)−0.0018 (5)−0.0009 (5)
C50.0202 (6)0.0173 (7)0.0157 (6)0.0013 (5)0.0014 (5)0.0001 (5)
C60.0148 (5)0.0160 (6)0.0144 (6)0.0001 (4)0.0010 (4)−0.0019 (5)
C70.0154 (5)0.0150 (6)0.0157 (6)−0.0013 (4)0.0036 (4)0.0021 (5)
C80.0157 (5)0.0162 (6)0.0167 (6)−0.0007 (4)0.0007 (4)0.0004 (5)
C90.0145 (5)0.0169 (6)0.0170 (6)0.0002 (4)0.0000 (4)0.0018 (5)
C100.0176 (5)0.0229 (7)0.0147 (6)−0.0007 (5)0.0012 (4)0.0041 (6)
C110.0168 (5)0.0153 (6)0.0150 (6)0.0006 (4)0.0030 (4)0.0017 (5)
C120.0223 (6)0.0249 (8)0.0164 (6)0.0014 (5)0.0067 (5)−0.0008 (6)
C130.0230 (6)0.0177 (7)0.0241 (7)0.0018 (5)0.0017 (5)0.0002 (6)
C140.0185 (6)0.0244 (8)0.0220 (7)0.0007 (5)−0.0030 (5)0.0038 (6)
O1—C71.4085 (17)C8—C91.5400 (19)
O1—H1O10.96 (2)C8—H8A1.029 (15)
N1—C111.3203 (16)C8—H8B1.012 (16)
N1—C11.3997 (17)C9—C131.528 (2)
N2—C111.3700 (17)C9—C141.5340 (18)
N2—C61.3965 (16)C9—C101.5378 (18)
N2—C71.4890 (16)C10—C111.4878 (18)
C1—C21.4000 (18)C10—H10A0.995 (16)
C1—C61.4060 (18)C10—H10B1.004 (16)
C2—C31.387 (2)C12—H12A0.976 (18)
C2—H2A0.988 (16)C12—H12B1.006 (17)
C3—C41.404 (2)C12—H12C0.998 (17)
C3—H1A0.979 (14)C13—H13A0.984 (16)
C4—C51.3886 (18)C13—H13B0.967 (17)
C4—H4A0.997 (15)C13—H13C1.009 (17)
C5—C61.3968 (18)C14—H14A1.000 (17)
C5—H5A0.961 (15)C14—H14B1.001 (18)
C7—C121.5271 (19)C14—H14C1.010 (17)
C7—C81.5450 (18)
C7—O1—H1O1108.6 (12)H8A—C8—H8B106.5 (12)
C11—N1—C1104.90 (11)C13—C9—C14109.35 (11)
C11—N2—C6106.65 (10)C13—C9—C10109.98 (11)
C11—N2—C7126.90 (10)C14—C9—C10109.00 (11)
C6—N2—C7126.43 (10)C13—C9—C8113.17 (11)
N1—C1—C2129.74 (12)C14—C9—C8108.46 (11)
N1—C1—C6109.93 (11)C10—C9—C8106.78 (10)
C2—C1—C6120.29 (12)C11—C10—C9110.96 (11)
C3—C2—C1117.79 (12)C11—C10—H10A107.7 (8)
C3—C2—H2A122.8 (9)C9—C10—H10A112.6 (8)
C1—C2—H2A119.4 (9)C11—C10—H10B108.4 (9)
C2—C3—C4121.33 (12)C9—C10—H10B109.2 (9)
C2—C3—H1A119.5 (9)H10A—C10—H10B108.0 (12)
C4—C3—H1A119.1 (9)N1—C11—N2113.35 (11)
C5—C4—C3121.67 (13)N1—C11—C10125.66 (12)
C5—C4—H4A118.4 (8)N2—C11—C10120.98 (11)
C3—C4—H4A119.9 (8)C7—C12—H12A112.3 (10)
C4—C5—C6116.79 (12)C7—C12—H12B106.4 (10)
C4—C5—H5A119.5 (9)H12A—C12—H12B112.6 (14)
C6—C5—H5A123.7 (9)C7—C12—H12C110.3 (10)
N2—C6—C5132.67 (11)H12A—C12—H12C108.8 (14)
N2—C6—C1105.13 (11)H12B—C12—H12C106.2 (14)
C5—C6—C1122.06 (11)C9—C13—H13A112.9 (9)
O1—C7—N2108.58 (10)C9—C13—H13B110.6 (9)
O1—C7—C12106.80 (10)H13A—C13—H13B106.9 (13)
N2—C7—C12109.84 (10)C9—C13—H13C111.5 (10)
O1—C7—C8110.08 (10)H13A—C13—H13C107.1 (13)
N2—C7—C8108.95 (10)H13B—C13—H13C107.4 (13)
C12—C7—C8112.51 (11)C9—C14—H14A111.9 (9)
C9—C8—C7118.09 (10)C9—C14—H14B109.3 (10)
C9—C8—H8A108.9 (9)H14A—C14—H14B107.6 (13)
C7—C8—H8A108.5 (9)C9—C14—H14C110.6 (10)
C9—C8—H8B108.3 (9)H14A—C14—H14C105.5 (13)
C7—C8—H8B106.0 (9)H14B—C14—H14C111.8 (14)
C11—N1—C1—C2−177.80 (14)C6—N2—C7—C12−58.00 (16)
C11—N1—C1—C6−0.14 (15)C11—N2—C7—C80.12 (17)
N1—C1—C2—C3176.20 (13)C6—N2—C7—C8178.34 (11)
C6—C1—C2—C3−1.2 (2)O1—C7—C8—C9148.09 (11)
C1—C2—C3—C4−1.3 (2)N2—C7—C8—C929.14 (15)
C2—C3—C4—C52.2 (2)C12—C7—C8—C9−92.92 (14)
C3—C4—C5—C6−0.5 (2)C7—C8—C9—C1364.20 (14)
C11—N2—C6—C5173.80 (14)C7—C8—C9—C14−174.28 (11)
C7—N2—C6—C5−4.7 (2)C7—C8—C9—C10−56.95 (15)
C11—N2—C6—C1−1.75 (14)C13—C9—C10—C11−68.67 (15)
C7—N2—C6—C1179.73 (11)C14—C9—C10—C11171.46 (11)
C4—C5—C6—N2−176.96 (13)C8—C9—C10—C1154.49 (14)
C4—C5—C6—C1−2.03 (19)C1—N1—C11—N2−1.04 (15)
N1—C1—C6—N21.20 (14)C1—N1—C11—C10177.57 (12)
C2—C1—C6—N2179.11 (11)C6—N2—C11—N11.82 (15)
N1—C1—C6—C5−174.94 (11)C7—N2—C11—N1−179.67 (11)
C2—C1—C6—C53.0 (2)C6—N2—C11—C10−176.86 (12)
C11—N2—C7—O1−119.77 (13)C7—N2—C11—C101.64 (19)
C6—N2—C7—O158.45 (16)C9—C10—C11—N1150.69 (13)
C11—N2—C7—C12123.78 (14)C9—C10—C11—N2−30.80 (17)
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N1i0.97 (2)1.84 (2)2.803 (2)174 (2)
C5—H5A···O1ii0.962 (15)2.499 (15)3.216 (2)131.3 (11)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1O1⋯N1i0.97 (2)1.84 (2)2.803 (2)174 (2)
C5—H5A⋯O1ii0.962 (15)2.499 (15)3.216 (2)131.3 (11)

Symmetry codes: (i) ; (ii) .

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1.  3-(2-Amino-5-nitro-anilino)-5,5-dimethyl-cyclo-hex-2-en-1-one 0.25-hydrate.

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