Literature DB >> 22199764

2-(3,4-Dimeth-oxy-phen-yl)-1H-benzimidazole.

Aliakbar Dehno Khalaji, Alireza Foroghnia, Mohammad Ali Khalilzadeh, Karla Fejfarová, Michal Dušek.

Abstract

In title compound, C(15)H(14)N(2)O(2), the dihedral angle between the 3,4-dimeth-oxy-phenyl group and the benzimidazole system is 26.47 (6)°. In the crystal, neighbouring mol-ecules are linked by N-H⋯N hydrogen bonds into C(4) chains propagating along the c-axis direction. The crystal structure also features weak C-H⋯O inter-actions.

Entities: Chemical Disease Species

Year: 2011 PMID： 22199764 PMCID： PMC3238911 DOI： 10.1107/S1600536811046897

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

Related literature

For a related structure, further synthetic details and background references to imidazolines, see: Khalaji et al. (2008 ▶). For related structures, see: Kia et al. (2008 ▶, 2009 ▶); Rashid et al. (2007 ▶).

Experimental

Crystal data

C15H14N2O2 M = 254.3 Orthorhombic, a = 9.2274 (8) Å b = 15.0109 (9) Å c = 9.2681 (3) Å V = 1283.74 (14) Å3 Z = 4 Cu Kα radiation μ = 0.72 mm−1 T = 120 K 0.40 × 0.21 × 0.09 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.75, T max = 1 12506 measured reflections 1982 independent reflections 1919 reflections with I > 3σ(I) R int = 0.024

Refinement

R[F 2 > 3σ(F 2)] = 0.026 wR(F 2) = 0.072 S = 1.46 1982 reflections 174 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.08 e Å−3 Δρmin = −0.11 e Å−3 Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046897/hb6490sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046897/hb6490Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811046897/hb6490Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₄N₂O₂	F(000) = 536
M_r = 254.3	D_x = 1.315 Mg m⁻³
Orthorhombic, Pca2₁	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2c -2ac	Cell parameters from 8286 reflections
a = 9.2274 (8) Å	θ = 2.9–67°
b = 15.0109 (9) Å	µ = 0.72 mm⁻¹
c = 9.2681 (3) Å	T = 120 K
V = 1283.74 (14) Å³	Slab, light yellow
Z = 4	0.40 × 0.21 × 0.09 mm

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1982 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1919 reflections with I > 3σ(I)
mirror	R_int = 0.024
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.1°, θ_min = 2.9°
Rotation method data acquisition using ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −17→17
T_min = 0.75, T_max = 1	l = −9→11
12506 measured reflections

Refinement on F²	54 constraints
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.072	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0016I²]
S = 1.46	(Δ/σ)_max = 0.047
1982 reflections	Δρ_max = 0.08 e Å⁻³
174 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints

Experimental. CrysAlisPro, Agilent Technologies (2010), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	U_iso*/U_eq
O1	0.50788 (10)	0.93193 (6)	0.50931 (11)	0.0289 (3)
O2	0.26137 (11)	0.89618 (7)	0.39223 (16)	0.0325 (3)
N1	0.77384 (12)	0.66702 (8)	0.08732 (18)	0.0233 (3)
N2	0.86211 (11)	0.69056 (8)	0.30939 (17)	0.0238 (3)
C1	0.75266 (14)	0.70471 (9)	0.21870 (18)	0.0226 (4)
C2	0.90804 (14)	0.62618 (9)	0.09065 (19)	0.0228 (4)
C3	0.98463 (15)	0.57777 (9)	−0.01205 (19)	0.0264 (4)
C4	1.11744 (15)	0.54402 (10)	0.0297 (2)	0.0281 (4)
C5	1.17424 (16)	0.55964 (9)	0.1677 (2)	0.0285 (4)
C6	1.09725 (15)	0.60805 (9)	0.2701 (2)	0.0268 (4)
C7	0.96186 (14)	0.64097 (9)	0.2299 (2)	0.0228 (4)
C8	0.62258 (13)	0.75563 (9)	0.25552 (18)	0.0238 (4)
C9	0.63170 (14)	0.82035 (9)	0.36407 (19)	0.0238 (4)
C10	0.51002 (15)	0.86699 (9)	0.4062 (2)	0.0244 (4)
C11	0.37543 (14)	0.84855 (10)	0.34023 (19)	0.0261 (4)
C12	0.36736 (14)	0.78589 (11)	0.2312 (2)	0.0293 (4)
C13	0.49052 (15)	0.73941 (10)	0.1886 (2)	0.0277 (4)
C14	0.63841 (15)	0.94452 (11)	0.5909 (2)	0.0311 (4)
C15	0.12101 (16)	0.87431 (12)	0.3367 (2)	0.0413 (5)
H3	0.947018	0.568253	−0.107386	0.0316*
H4	1.172283	0.508955	−0.037558	0.0337*
H5	1.268095	0.53647	0.191941	0.0342*
H6	1.135836	0.618397	0.364821	0.0322*
H9	0.723198	0.832316	0.409397	0.0286*
H12	0.276306	0.774417	0.184648	0.0352*
H13	0.48424	0.696024	0.112722	0.0333*
H14a	0.62263	0.989168	0.663353	0.0467*
H14b	0.665129	0.889441	0.636306	0.0467*
H14c	0.714823	0.963371	0.527559	0.0467*
H15a	0.049359	0.91136	0.381853	0.062*
H15b	0.119532	0.883995	0.234322	0.062*
H15c	0.10002	0.812894	0.356683	0.062*
H1	0.7167 (18)	0.6702 (11)	0.008 (2)	0.028*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0310 (5)	0.0286 (5)	0.0270 (6)	0.0021 (4)	−0.0007 (4)	−0.0067 (4)
O2	0.0253 (5)	0.0362 (6)	0.0359 (6)	0.0074 (4)	−0.0002 (4)	−0.0064 (5)
N1	0.0238 (5)	0.0285 (6)	0.0176 (6)	0.0003 (4)	−0.0005 (5)	−0.0009 (5)
N2	0.0239 (5)	0.0289 (6)	0.0186 (6)	0.0017 (4)	0.0007 (4)	−0.0010 (5)
C1	0.0249 (6)	0.0252 (6)	0.0178 (6)	−0.0029 (5)	0.0022 (5)	0.0003 (5)
C2	0.0240 (6)	0.0233 (6)	0.0209 (7)	−0.0025 (5)	0.0012 (6)	0.0026 (5)
C3	0.0316 (7)	0.0282 (7)	0.0193 (7)	−0.0032 (6)	0.0030 (5)	−0.0011 (5)
C4	0.0299 (7)	0.0274 (7)	0.0268 (7)	0.0015 (5)	0.0081 (6)	−0.0009 (6)
C5	0.0260 (7)	0.0315 (7)	0.0281 (7)	0.0037 (6)	0.0017 (6)	0.0022 (6)
C6	0.0262 (6)	0.0319 (7)	0.0224 (8)	0.0003 (5)	−0.0016 (5)	−0.0005 (6)
C7	0.0241 (6)	0.0250 (7)	0.0193 (7)	−0.0016 (5)	0.0035 (6)	0.0004 (5)
C8	0.0255 (7)	0.0255 (7)	0.0205 (7)	0.0008 (5)	0.0008 (5)	0.0014 (5)
C9	0.0247 (6)	0.0264 (7)	0.0204 (7)	−0.0004 (5)	−0.0001 (5)	0.0020 (6)
C10	0.0304 (7)	0.0236 (7)	0.0193 (7)	−0.0002 (5)	0.0023 (5)	0.0015 (6)
C11	0.0265 (7)	0.0280 (7)	0.0238 (7)	0.0028 (5)	0.0033 (5)	0.0019 (6)
C12	0.0259 (7)	0.0362 (8)	0.0258 (8)	0.0018 (5)	−0.0037 (6)	−0.0014 (6)
C13	0.0303 (7)	0.0314 (7)	0.0215 (7)	−0.0001 (6)	−0.0013 (5)	−0.0030 (6)
C14	0.0336 (7)	0.0308 (8)	0.0291 (8)	−0.0019 (5)	−0.0021 (6)	−0.0070 (6)
C15	0.0282 (8)	0.0531 (10)	0.0428 (11)	0.0092 (7)	−0.0067 (7)	−0.0144 (8)

O1—C10	1.3651 (18)	C6—C7	1.3942 (19)
O1—C14	1.4345 (18)	C6—H6	0.96
O2—C11	1.3606 (18)	C8—C9	1.401 (2)
O2—C15	1.4319 (19)	C8—C13	1.389 (2)
N1—C1	1.357 (2)	C9—C10	1.380 (2)
N1—C2	1.3820 (17)	C9—H9	0.96
N1—H1	0.903 (19)	C10—C11	1.412 (2)
N2—C1	1.331 (2)	C11—C12	1.383 (2)
N2—C7	1.3943 (19)	C12—C13	1.391 (2)
C1—C8	1.4633 (19)	C12—H12	0.96
C2—C3	1.391 (2)	C13—H13	0.96
C2—C7	1.401 (2)	C14—H14a	0.96
C3—C4	1.381 (2)	C14—H14b	0.96
C3—H3	0.96	C14—H14c	0.96
C4—C5	1.402 (3)	C15—H15a	0.96
C4—H4	0.96	C15—H15b	0.96
C5—C6	1.391 (2)	C15—H15c	0.96
C5—H5	0.96

C10—O1—C14	116.79 (11)	C9—C8—C13	119.67 (12)
C11—O2—C15	116.86 (13)	C8—C9—C10	120.42 (13)
C1—N1—C2	107.09 (13)	C8—C9—H9	119.7897
C1—N1—H1	128.4 (11)	C10—C9—H9	119.7883
C2—N1—H1	124.4 (11)	O1—C10—C9	124.92 (13)
C1—N2—C7	104.62 (14)	O1—C10—C11	115.50 (12)
N1—C1—N2	113.01 (12)	C9—C10—C11	119.59 (15)
N1—C1—C8	123.04 (13)	O2—C11—C10	115.09 (14)
N2—C1—C8	123.95 (15)	O2—C11—C12	125.08 (13)
N1—C2—C3	132.21 (16)	C10—C11—C12	119.83 (13)
N1—C2—C7	105.55 (13)	C11—C12—C13	120.32 (13)
C3—C2—C7	122.23 (13)	C11—C12—H12	119.839
C2—C3—C4	116.80 (16)	C13—C12—H12	119.8382
C2—C3—H3	121.5999	C8—C13—C12	120.14 (15)
C4—C3—H3	121.5996	C8—C13—H13	119.9308
C3—C4—C5	121.72 (15)	C12—C13—H13	119.9316
C3—C4—H4	119.1383	O1—C14—H14a	109.4704
C5—C4—H4	119.138	O1—C14—H14b	109.4712
C4—C5—C6	121.28 (14)	O1—C14—H14c	109.4714
C4—C5—H5	119.362	H14a—C14—H14b	109.4712
C6—C5—H5	119.3623	H14a—C14—H14c	109.471
C5—C6—C7	117.42 (16)	H14b—C14—H14c	109.4722
C5—C6—H6	121.2877	O2—C15—H15a	109.4714
C7—C6—H6	121.2879	O2—C15—H15b	109.4715
N2—C7—C2	109.72 (12)	O2—C15—H15c	109.4712
N2—C7—C6	129.76 (16)	H15a—C15—H15b	109.4715
C2—C7—C6	120.52 (14)	H15a—C15—H15c	109.4712
C1—C8—C9	118.71 (12)	H15b—C15—H15c	109.4705
C1—C8—C13	121.59 (14)

C9—C10—O1—C14	−7.8 (2)	N1—C1—C8—C9	−154.38 (14)
C10—C11—O2—C15	−174.97 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14c···O2ⁱ	0.96	2.49	3.224 (2)	133
C15—H15b···O1ⁱⁱ	0.96	2.50	3.372 (2)	151
N1—H1···N2ⁱⁱⁱ	0.903 (19)	2.01 (2)	2.887 (2)	164.6 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14c⋯O2ⁱ	0.96	2.49	3.224 (2)	133
C15—H15b⋯O1ⁱⁱ	0.96	2.50	3.372 (2)	151
N1—H1⋯N2ⁱⁱⁱ	0.903 (19)	2.01 (2)	2.887 (2)	164.6 (16)

Symmetry codes: (i) ; (ii) ; (iii) .

3 in total

2-(3,4-Dimeth-oxy-phen-yl)-1H-benzimidazole.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. 2-(3,4,5-Trimethoxy-phen-yl)-1H-benzimidazole.

2. 2-[4-(4,5-Dihydro-1H-pyrrol-2-yl)phen-yl]-4,5-dihydro-1H-imidazole.

3. 2-(3-Chloro-phen-yl)-4,5-dihydro-1H-imidazole.