4-Methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid.

In the title compound, C(12)H(14)N(2)O(2), the benzene ring and imidazole ring are almost coplanar, making a dihedral angle of 2.47 (14)°. Inter-molecular O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For the use of the title compound as an inter­mediate in the preparation of telmisartan, see: Ries et al. (1993 ▶). For the biological activity of telmisartan, see: Engeli et al. (2000 ▶); Goossens et al. (2003 ▶). For reference structural data, see: Allen et al. (1987 ▶). For related literature, see: Kintscher et al. (2004 ▶).

Experimental

Crystal data

C12H14N2O2

M = 218.25

Tetragonal,

a = 12.0548 (17) Å

c = 31.899 (6) Å

V = 4635.5 (13) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonuis CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.975, T max = 0.991

4426 measured reflections

2105 independent reflections

1304 reflections with I > 2σ(I)

R int = 0.042

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.195

S = 1.00

2105 reflections

133 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius,1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043420/sj2567sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043420/sj2567Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H14N2O2	Dx = 1.251 Mg m−3
Mr = 218.25	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 25 reflections
Hall symbol: -I 4ad	θ = 10–13°
a = 12.0548 (17) Å	µ = 0.09 mm−1
c = 31.899 (6) Å	T = 293 K
V = 4635.5 (13) Å3	Block, colorless
Z = 16	0.30 × 0.30 × 0.10 mm
F(000) = 1856

Enraf–Nonuis CAD-4 diffractometer	1304 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 25.2°, θmin = 1.8°
ω/2θ scans	h = −9→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.975, Tmax = 0.991	l = 0→38
4426 measured reflections	3 standard reflections every 200 reflections
2105 independent reflections	intensity decay: none

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)] = 0.072	H-atom parameters constrained
wR(F2) = 0.195	w = 1/[σ2(Fo2) + (0.1P)2 + 5P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2105 reflections	Δρmax = 0.62 e Å−3
133 parameters	Δρmin = −0.39 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (3)

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.

	x	y	z	Uiso*/Ueq
O1	0.7815 (2)	0.4947 (2)	0.07388 (7)	0.0591 (8)
O2	0.7256 (2)	0.32125 (18)	0.07006 (6)	0.0471 (7)
H2C	0.7077	0.3341	0.0944	0.071*
N1	0.8807 (2)	0.3584 (2)	−0.11544 (7)	0.0376 (7)
N2	0.8170 (2)	0.2123 (2)	−0.08282 (7)	0.0420 (7)
H2D	0.7940	0.1458	−0.0785	0.050*
C1	0.6545 (5)	0.2486 (5)	−0.18175 (17)	0.104
H1B	0.5891	0.2171	−0.1941	0.155*
H1C	0.6843	0.3042	−0.2001	0.155*
H1D	0.6358	0.2818	−0.1553	0.155*
C2	0.7407 (4)	0.1577 (5)	−0.17491 (18)	0.100
H2A	0.7097	0.1043	−0.1554	0.120*
H2B	0.7513	0.1195	−0.2014	0.120*
C3	0.8501 (3)	0.1904 (3)	−0.15925 (10)	0.0561 (10)
H3A	0.8860	0.2355	−0.1805	0.067*
H3B	0.8945	0.1239	−0.1557	0.067*
C4	0.8509 (3)	0.2525 (3)	−0.11926 (9)	0.0402 (8)
C5	0.8656 (2)	0.3874 (3)	−0.07355 (9)	0.0324 (7)
C6	0.8820 (2)	0.4885 (2)	−0.05283 (9)	0.0341 (7)
C7	0.8539 (2)	0.4896 (3)	−0.01107 (9)	0.0351 (7)
H7A	0.8653	0.5543	0.0042	0.042*
C8	0.8085 (2)	0.3966 (2)	0.00960 (9)	0.0315 (7)
C9	0.7938 (3)	0.2969 (2)	−0.01128 (9)	0.0353 (8)
H9A	0.7645	0.2350	0.0021	0.042*
C10	0.8246 (3)	0.2941 (2)	−0.05289 (9)	0.0325 (7)
C11	0.9269 (3)	0.5876 (3)	−0.07572 (11)	0.0523 (10)
H11A	0.9410	0.5681	−0.1044	0.078*
H11B	0.9947	0.6112	−0.0627	0.078*
H11C	0.8737	0.6467	−0.0747	0.078*
C12	0.7704 (3)	0.4069 (2)	0.05433 (9)	0.0352 (7)

	U11	U22	U33	U12	U13	U23
O1	0.097 (2)	0.0411 (14)	0.0391 (14)	−0.0157 (14)	0.0171 (13)	−0.0130 (11)
O2	0.0713 (17)	0.0394 (13)	0.0306 (12)	−0.0073 (12)	0.0238 (11)	−0.0056 (10)
N1	0.0401 (16)	0.0475 (17)	0.0250 (13)	0.0030 (13)	0.0022 (11)	0.0055 (12)
N2	0.0599 (19)	0.0366 (15)	0.0295 (13)	−0.0022 (13)	0.0098 (13)	0.0006 (12)
C1	0.104	0.104	0.104	0.000	0.000	0.000
C2	0.100	0.100	0.100	0.000	0.000	0.000
C3	0.062 (2)	0.079 (3)	0.0275 (18)	0.006 (2)	0.0032 (16)	−0.0106 (17)
C4	0.0392 (19)	0.056 (2)	0.0250 (16)	0.0079 (16)	0.0066 (14)	0.0000 (15)
C5	0.0309 (16)	0.0392 (18)	0.0271 (15)	0.0063 (13)	0.0052 (13)	0.0077 (13)
C6	0.0356 (17)	0.0303 (17)	0.0365 (17)	−0.0015 (13)	0.0005 (14)	0.0093 (13)
C7	0.0379 (18)	0.0330 (17)	0.0345 (16)	−0.0008 (13)	0.0032 (13)	−0.0027 (13)
C8	0.0410 (18)	0.0273 (16)	0.0261 (15)	0.0038 (13)	0.0033 (13)	0.0040 (12)
C9	0.0472 (19)	0.0318 (17)	0.0269 (16)	−0.0020 (14)	0.0091 (13)	0.0032 (13)
C10	0.0454 (19)	0.0293 (16)	0.0229 (14)	0.0015 (13)	0.0046 (13)	0.0015 (12)
C11	0.064 (2)	0.041 (2)	0.052 (2)	−0.0089 (17)	0.0104 (18)	0.0146 (17)
C12	0.0430 (19)	0.0321 (17)	0.0305 (16)	0.0009 (14)	0.0040 (14)	−0.0042 (14)

O1—C12	1.237 (4)	C3—H3A	0.9700
O2—C12	1.268 (3)	C3—H3B	0.9700
O2—H2C	0.8200	C5—C10	1.394 (4)
N1—C4	1.332 (4)	C5—C6	1.400 (4)
N1—C5	1.393 (4)	C6—C7	1.374 (4)
N2—C4	1.324 (4)	C6—C11	1.501 (4)
N2—C10	1.376 (4)	C7—C8	1.411 (4)
N2—H2D	0.8600	C7—H7A	0.9300
C1—C2	1.526 (6)	C8—C9	1.385 (4)
C1—H1B	0.9600	C8—C12	1.504 (4)
C1—H1C	0.9600	C9—C10	1.379 (4)
C1—H1D	0.9600	C9—H9A	0.9300
C2—C3	1.465 (6)	C11—H11A	0.9600
C2—H2A	0.9700	C11—H11B	0.9600
C2—H2B	0.9700	C11—H11C	0.9600
C3—C4	1.479 (4)
C12—O2—H2C	109.5	N1—C5—C6	130.7 (3)
C4—N1—C5	107.0 (2)	C10—C5—C6	121.9 (3)
C4—N2—C10	109.1 (3)	C7—C6—C5	115.5 (3)
C4—N2—H2D	125.5	C7—C6—C11	123.5 (3)
C10—N2—H2D	125.5	C5—C6—C11	120.9 (3)
C2—C1—H1B	109.5	C6—C7—C8	122.7 (3)
C2—C1—H1C	109.5	C6—C7—H7A	118.6
H1B—C1—H1C	109.5	C8—C7—H7A	118.6
C2—C1—H1D	109.5	C9—C8—C7	120.9 (3)
H1B—C1—H1D	109.5	C9—C8—C12	119.2 (3)
H1C—C1—H1D	109.5	C7—C8—C12	119.8 (3)
C3—C2—C1	118.0 (5)	C10—C9—C8	116.7 (3)
C3—C2—H2A	107.8	C10—C9—H9A	121.6
C1—C2—H2A	107.8	C8—C9—H9A	121.6
C3—C2—H2B	107.8	N2—C10—C9	131.9 (3)
C1—C2—H2B	107.8	N2—C10—C5	105.9 (2)
H2A—C2—H2B	107.2	C9—C10—C5	122.1 (3)
C2—C3—C4	115.8 (4)	C6—C11—H11A	109.5
C2—C3—H3A	108.3	C6—C11—H11B	109.5
C4—C3—H3A	108.3	H11A—C11—H11B	109.5
C2—C3—H3B	108.3	C6—C11—H11C	109.5
C4—C3—H3B	108.3	H11A—C11—H11C	109.5
H3A—C3—H3B	107.4	H11B—C11—H11C	109.5
N2—C4—N1	110.7 (3)	O1—C12—O2	122.9 (3)
N2—C4—C3	124.8 (3)	O1—C12—C8	121.1 (3)
N1—C4—C3	124.5 (3)	O2—C12—C8	116.0 (3)
N1—C5—C10	107.3 (3)
C1—C2—C3—C4	56.3 (6)	C6—C7—C8—C12	−174.6 (3)
C10—N2—C4—N1	−0.2 (4)	C7—C8—C9—C10	−0.6 (5)
C10—N2—C4—C3	−177.3 (3)	C12—C8—C9—C10	176.5 (3)
C5—N1—C4—N2	0.5 (4)	C4—N2—C10—C9	175.5 (3)
C5—N1—C4—C3	177.5 (3)	C4—N2—C10—C5	−0.1 (4)
C2—C3—C4—N2	63.9 (5)	C8—C9—C10—N2	−176.8 (3)
C2—C3—C4—N1	−112.7 (4)	C8—C9—C10—C5	−1.8 (5)
C4—N1—C5—C10	−0.5 (3)	N1—C5—C10—N2	0.4 (3)
C4—N1—C5—C6	−178.6 (3)	C6—C5—C10—N2	178.6 (3)
N1—C5—C6—C7	177.2 (3)	N1—C5—C10—C9	−175.7 (3)
C10—C5—C6—C7	−0.6 (4)	C6—C5—C10—C9	2.5 (5)
N1—C5—C6—C11	−2.5 (5)	C9—C8—C12—O1	−179.5 (3)
C10—C5—C6—C11	179.7 (3)	C7—C8—C12—O1	−2.4 (5)
C5—C6—C7—C8	−1.8 (4)	C9—C8—C12—O2	−0.4 (4)
C11—C6—C7—C8	177.9 (3)	C7—C8—C12—O2	176.7 (3)
C6—C7—C8—C9	2.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O2i	0.97	2.56	3.399 (4)	144
C11—H11A···O2ii	0.96	2.66	3.587 (4)	163
O2—H2C···N1iii	0.82	1.80	2.562 (3)	153
N2—H2D···O1iv	0.86	1.83	2.673 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O2i	0.97	2.56	3.399 (4)	144
C11—H11A⋯O2ii	0.96	2.66	3.587 (4)	163
O2—H2C⋯N1iii	0.82	1.80	2.562 (3)	153
N2—H2D⋯O1iv	0.86	1.83	2.673 (3)	165

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