2-Benzoyl-1H-benzimidazole

Ai, L.; Shen, X.-M.; Ng, S.W.

doi:10.1107/S1600536810045666

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3164

https://doi.org/10.1107/S1600536810045666

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2-Benzoyl-1H-benzimidazole

Lin Ai,^a Xiu-Min Shen ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry, Beijing Normal University, Beijing 100875, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 6 November 2010; accepted 7 November 2010; online 13 November 2010)

In the title compound, C₁₄H₁₀N₂O, the benzoyl ring and benzimidazole ring system are aligned at a dihedral angle of 50.2 (2)°. In the crystal, intermolecular N—H⋯N hydrogen bonds between adjacent imidazole groups generate supramolecular C(4) chains running along the b axis.

Related literature

For phototropism of 2-acetylbenzimidazole and 2-benzoylbenzimidazole, see: Chowdhury et al. (2005 ). For the crystal structure of 2-acetylbenzimidazole, see: Yang et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₀N₂O
M_r = 222.24
Orthorhombic, P b c a
a = 14.7356 (8) Å
b = 9.9530 (12) Å
c = 15.7981 (12) Å
V = 2317.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
10324 measured reflections
2658 independent reflections
1885 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.115
S = 1.01
2658 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.90 (2)	1.95 (2)	2.829 (2)	164 (1)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045666/xu5084sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045666/xu5084Isup2.hkl

checkCIF report

Comment top

Acetyl-2-benzimidazole and benzoyl-2-benzimidazole are reported to exhibit excited-state prototropism in solvents at different pH levels (Chowdhury et al., 2005). Acetyl-2-benzimidazole exists in the solid state as an N–H···O hydrogen bonded dimer; the molecule is essentially planar (Yang et al., 2006). With the larger phenyl ring in place of the methyl group, the aromatic analog (Scheme I) requires rotation of the aromatic ring in order to reduce strain; this is reflected in the 50.2 (2) ° dihedral angle between the phenyl and benzimidazolyl rings (Fig. 1). Adjacent molecules are linked into a chan by N–H···O hydrogen bonds (Fig. 2).

Related literature top

For phototropism of 2-acetylbenzimidazole and 2-benzoylbenzimidazole, see: Chowdhury et al. (2005). For the crystal structure of 2-acetylbenzimidazole, see: Yang et al. (2006).

Experimental top

The compound was synthesized by using a literature procedure (Chowdhury et al., 2005), and crystals were grown from a methanol solution of the compound.

Structure description top

For phototropism of 2-acetylbenzimidazole and 2-benzoylbenzimidazole, see: Chowdhury et al. (2005). For the crystal structure of 2-acetylbenzimidazole, see: Yang et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₄H₁₁N₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain structure.

2-Benzoyl-1H-benzimidazole top

Crystal data top

C₁₄H₁₀N₂O	F(000) = 928
M_r = 222.24	D_x = 1.274 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2496 reflections
a = 14.7356 (8) Å	θ = 2.8–26.7°
b = 9.9530 (12) Å	µ = 0.08 mm⁻¹
c = 15.7981 (12) Å	T = 293 K
V = 2317.0 (4) Å³	Block, colorless
Z = 8	0.40 × 0.40 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	1885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 2.8°
ω scans	h = −10→19
10324 measured reflections	k = −12→11
2658 independent reflections	l = −15→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0549P)² + 0.2609P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2658 reflections	Δρ_max = 0.16 e Å⁻³
159 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0093 (12)

Crystal data top

C₁₄H₁₀N₂O	V = 2317.0 (4) Å³
M_r = 222.24	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.7356 (8) Å	µ = 0.08 mm⁻¹
b = 9.9530 (12) Å	T = 293 K
c = 15.7981 (12) Å	0.40 × 0.40 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	1885 reflections with I > 2σ(I)
10324 measured reflections	R_int = 0.030
2658 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.16 e Å⁻³
2658 reflections	Δρ_min = −0.14 e Å⁻³
159 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.38338 (7)	0.51103 (10)	0.45822 (7)	0.0647 (3)
N1	0.23286 (7)	0.52044 (10)	0.35142 (7)	0.0456 (3)
H1	0.2500 (10)	0.6048 (17)	0.3643 (9)	0.066 (4)*
N2	0.22405 (7)	0.29711 (9)	0.35955 (7)	0.0450 (3)
C1	0.16927 (9)	0.48272 (12)	0.29302 (8)	0.0446 (3)
C2	0.11547 (10)	0.55500 (15)	0.23652 (9)	0.0609 (4)
H2	0.1189	0.6481	0.2328	0.073*
C3	0.05747 (12)	0.48239 (18)	0.18687 (10)	0.0733 (5)
H3	0.0207	0.5274	0.1483	0.088*
C4	0.05192 (13)	0.34275 (18)	0.19233 (10)	0.0767 (5)
H4	0.0111	0.2972	0.1577	0.092*
C5	0.10482 (11)	0.27110 (15)	0.24714 (10)	0.0647 (4)
H5	0.1011	0.1779	0.2501	0.078*
C6	0.16460 (9)	0.34273 (12)	0.29846 (8)	0.0453 (3)
C7	0.26312 (9)	0.40660 (11)	0.38936 (7)	0.0411 (3)
C8	0.33717 (9)	0.41037 (12)	0.45261 (8)	0.0444 (3)
C9	0.35378 (9)	0.28972 (13)	0.50523 (8)	0.0471 (3)
C10	0.28375 (11)	0.21174 (15)	0.53695 (9)	0.0613 (4)
H10	0.2238	0.2326	0.5240	0.074*
C11	0.30339 (17)	0.10285 (19)	0.58787 (11)	0.0904 (7)
H11	0.2566	0.0520	0.6110	0.108*
C12	0.3922 (2)	0.0697 (2)	0.60441 (13)	0.1081 (8)
H12	0.4052	−0.0053	0.6373	0.130*
C13	0.46157 (16)	0.1462 (2)	0.57286 (13)	0.0942 (7)
H13	0.5214	0.1224	0.5840	0.113*
C14	0.44330 (11)	0.25789 (16)	0.52484 (9)	0.0632 (4)
H14	0.4904	0.3119	0.5055	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0593 (6)	0.0444 (6)	0.0904 (8)	−0.0143 (5)	−0.0074 (5)	0.0005 (5)
N1	0.0576 (7)	0.0243 (5)	0.0551 (6)	−0.0016 (5)	0.0001 (5)	0.0018 (5)
N2	0.0574 (7)	0.0269 (5)	0.0506 (6)	−0.0008 (4)	−0.0037 (5)	0.0015 (4)
C1	0.0526 (7)	0.0335 (6)	0.0477 (7)	0.0013 (5)	0.0040 (6)	0.0032 (5)
C2	0.0731 (10)	0.0441 (8)	0.0656 (9)	0.0079 (7)	−0.0038 (8)	0.0136 (7)
C3	0.0784 (11)	0.0751 (11)	0.0663 (9)	0.0043 (9)	−0.0174 (9)	0.0174 (9)
C4	0.0894 (13)	0.0752 (12)	0.0656 (9)	−0.0134 (10)	−0.0262 (9)	0.0048 (9)
C5	0.0858 (11)	0.0455 (8)	0.0630 (8)	−0.0114 (7)	−0.0168 (8)	0.0004 (7)
C6	0.0561 (8)	0.0329 (6)	0.0469 (6)	−0.0008 (5)	−0.0013 (6)	0.0019 (5)
C7	0.0486 (7)	0.0273 (6)	0.0475 (6)	−0.0014 (5)	0.0044 (5)	0.0009 (5)
C8	0.0437 (7)	0.0354 (6)	0.0543 (7)	−0.0020 (5)	0.0046 (6)	−0.0045 (6)
C9	0.0559 (8)	0.0403 (7)	0.0450 (6)	−0.0009 (6)	−0.0049 (6)	−0.0037 (6)
C10	0.0725 (10)	0.0583 (9)	0.0531 (8)	−0.0141 (7)	−0.0062 (7)	0.0077 (7)
C11	0.1331 (19)	0.0743 (12)	0.0637 (10)	−0.0338 (12)	−0.0211 (11)	0.0238 (9)
C12	0.160 (2)	0.0778 (14)	0.0864 (13)	−0.0021 (15)	−0.0520 (15)	0.0288 (11)
C13	0.1035 (16)	0.0826 (14)	0.0967 (14)	0.0211 (12)	−0.0447 (12)	0.0051 (12)
C14	0.0632 (9)	0.0625 (9)	0.0641 (9)	0.0056 (7)	−0.0151 (7)	−0.0065 (7)

Geometric parameters (Å, º) top

O1—C8	1.2146 (14)	C5—H5	0.9300
N1—C7	1.3571 (15)	C7—C8	1.4800 (18)
N1—C1	1.3677 (17)	C8—C9	1.4809 (18)
N1—H1	0.900 (17)	C9—C10	1.3851 (19)
N2—C7	1.3195 (15)	C9—C14	1.392 (2)
N2—C6	1.3802 (16)	C10—C11	1.380 (2)
C1—C2	1.3938 (19)	C10—H10	0.9300
C1—C6	1.3977 (17)	C11—C12	1.375 (3)
C2—C3	1.367 (2)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.369 (3)
C3—C4	1.395 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.372 (2)
C4—C5	1.366 (2)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.3933 (19)

C7—N1—C1	107.09 (10)	N2—C7—C8	125.70 (11)
C7—N1—H1	125.9 (10)	N1—C7—C8	121.28 (10)
C1—N1—H1	127.0 (10)	O1—C8—C7	118.92 (12)
C7—N2—C6	104.76 (10)	O1—C8—C9	122.35 (12)
N1—C1—C2	132.85 (12)	C7—C8—C9	118.71 (10)
N1—C1—C6	105.42 (11)	C10—C9—C14	119.88 (13)
C2—C1—C6	121.73 (13)	C10—C9—C8	122.30 (13)
C3—C2—C1	116.76 (14)	C14—C9—C8	117.79 (13)
C3—C2—H2	121.6	C11—C10—C9	119.64 (17)
C1—C2—H2	121.6	C11—C10—H10	120.2
C2—C3—C4	121.88 (15)	C9—C10—H10	120.2
C2—C3—H3	119.1	C12—C11—C10	119.92 (19)
C4—C3—H3	119.1	C12—C11—H11	120.0
C5—C4—C3	121.72 (15)	C10—C11—H11	120.0
C5—C4—H4	119.1	C13—C12—C11	120.55 (18)
C3—C4—H4	119.1	C13—C12—H12	119.7
C4—C5—C6	117.55 (14)	C11—C12—H12	119.7
C4—C5—H5	121.2	C12—C13—C14	120.36 (19)
C6—C5—H5	121.2	C12—C13—H13	119.8
N2—C6—C5	129.77 (12)	C14—C13—H13	119.8
N2—C6—C1	109.86 (11)	C13—C14—C9	119.56 (17)
C5—C6—C1	120.36 (12)	C13—C14—H14	120.2
N2—C7—N1	112.86 (11)	C9—C14—H14	120.2

C7—N1—C1—C2	179.42 (14)	C1—N1—C7—C8	176.10 (11)
C7—N1—C1—C6	−0.39 (14)	N2—C7—C8—O1	160.44 (13)
N1—C1—C2—C3	−179.47 (15)	N1—C7—C8—O1	−14.80 (19)
C6—C1—C2—C3	0.3 (2)	N2—C7—C8—C9	−17.95 (19)
C1—C2—C3—C4	0.2 (2)	N1—C7—C8—C9	166.81 (11)
C2—C3—C4—C5	−0.6 (3)	O1—C8—C9—C10	142.64 (14)
C3—C4—C5—C6	0.5 (3)	C7—C8—C9—C10	−39.03 (18)
C7—N2—C6—C5	−179.18 (15)	O1—C8—C9—C14	−35.36 (19)
C7—N2—C6—C1	−0.19 (14)	C7—C8—C9—C14	142.97 (12)
C4—C5—C6—N2	178.85 (14)	C14—C9—C10—C11	0.0 (2)
C4—C5—C6—C1	0.0 (2)	C8—C9—C10—C11	−177.95 (14)
N1—C1—C6—N2	0.37 (14)	C9—C10—C11—C12	−2.2 (3)
C2—C1—C6—N2	−179.47 (12)	C10—C11—C12—C13	2.0 (3)
N1—C1—C6—C5	179.46 (13)	C11—C12—C13—C14	0.6 (3)
C2—C1—C6—C5	−0.4 (2)	C12—C13—C14—C9	−2.8 (3)
C6—N2—C7—N1	−0.06 (14)	C10—C9—C14—C13	2.5 (2)
C6—N2—C7—C8	−175.65 (11)	C8—C9—C14—C13	−179.45 (14)
C1—N1—C7—N2	0.29 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.90 (2)	1.95 (2)	2.829 (2)	164 (1)

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O
M_r	222.24
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	14.7356 (8), 9.9530 (12), 15.7981 (12)
V (Å³)	2317.0 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10324, 2658, 1885
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.01
No. of reflections	2658
No. of parameters	159
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.90 (2)	1.95 (2)	2.829 (2)	164 (1)

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

We thank Beijing Normal University and the University of Malaya for supporting this study.

References

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