Methyl 4-(1H-benzimidazol-2-yl)benzoate trihydrate.

The title compound, C(15)H(12)N(2)O(2)·3H(2)O, has been prepared from the reaction of a Schiff base of benzene-1,2-diamine and iron perchlorate at room temperature. The dihedral angle between the benzimidazole ring and the 4-substituted benzene ring is 0.47 (3)°. Hydrogen bonding involving water mol-ecules, imidazole N, imidazole imine H and ester O atoms stabilizes the crystal structure.

Related literature

For literature on the pharmacological activities of benzimidazole and its derivatives, see: Matsui et al. (1994 ▶); Ries et al. (2003 ▶). For the 4-nitro analogue, see: Wu (2009 ▶). For the earlier reported structure, see: Bei et al. (2000 ▶). For the synthesis of imidazoles and benzimidazoles, see: Du & Wang (2007 ▶).

Experimental

Crystal data

C15H12N2O2·3H2O

M = 306.32

Triclinic,

a = 6.8308 (3) Å

b = 10.8165 (5) Å

c = 11.5254 (8) Å

α = 114.718 (3)°

β = 101.718 (4)°

γ = 97.621 (2)°

V = 734.41 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.41 × 0.12 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

10457 measured reflections

3194 independent reflections

2873 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.142

S = 1.02

3194 reflections

218 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.41 e Å−3

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: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039188/ds2060sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039188/ds2060Isup2.hkl

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

C15H12N2O2·3H2O	Z = 2
Mr = 306.32	F(000) = 324
Triclinic, P1	Dx = 1.390 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8308 (3) Å	Cell parameters from 8743 reflections
b = 10.8165 (5) Å	θ = 2.2–40.7°
c = 11.5254 (8) Å	µ = 0.11 mm−1
α = 114.718 (3)°	T = 296 K
β = 101.718 (4)°	Rod, colourless
γ = 97.621 (2)°	0.41 × 0.12 × 0.12 mm
V = 734.41 (7) Å3

Bruker APEXII CCD area-detector diffractometer	2873 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
graphite	θmax = 27.0°, θmin = 2.0°
φ and ω scans	h = −8→7
10457 measured reflections	k = −13→13
3194 independent reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.1051P)2 + 0.1366P] where P = (Fo2 + 2Fc2)/3
3194 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.41 e Å−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	0.31311 (14)	0.28296 (9)	0.39119 (8)	0.0166 (2)
O5	0.21253 (15)	0.02407 (10)	0.63276 (9)	0.0209 (2)
H21	0.155 (3)	−0.050 (2)	0.554 (2)	0.031*
H20	0.122 (3)	0.076 (2)	0.6355 (19)	0.031*
O3	0.37646 (14)	0.87010 (9)	0.26610 (9)	0.0176 (2)
H17	0.523 (3)	0.9011 (18)	0.3003 (17)	0.026*
H16	0.333 (3)	0.9357 (19)	0.2506 (17)	0.026*
O2	0.22975 (14)	0.07258 (9)	0.20910 (9)	0.0182 (2)
O4	0.07060 (15)	0.80876 (9)	0.37434 (9)	0.0207 (2)
H19	−0.003 (3)	0.723 (2)	0.3151 (19)	0.031*
H18	0.170 (3)	0.8188 (19)	0.3397 (19)	0.031*
N1	0.19210 (15)	0.44471 (10)	−0.18336 (10)	0.0133 (2)
N2	0.28539 (14)	0.64581 (10)	0.00717 (9)	0.0124 (2)
H2	0.3197	0.7017	0.0912	0.015*
C1	0.3320 (2)	0.21255 (13)	0.47386 (13)	0.0211 (3)
H1A	0.2092	0.1397	0.4436	0.032*
H1B	0.3504	0.2790	0.5647	0.032*
H1C	0.4488	0.1722	0.4682	0.032*
C2	0.26140 (17)	0.20014 (12)	0.25945 (12)	0.0135 (3)
C3	0.24921 (17)	0.28025 (12)	0.18125 (11)	0.0127 (3)
C4	0.29491 (18)	0.42689 (12)	0.24419 (12)	0.0146 (3)
H4	0.3289	0.4763	0.3366	0.018*
C5	0.28948 (18)	0.49866 (12)	0.16823 (12)	0.0146 (3)
H5	0.3193	0.5962	0.2104	0.017*
C6	0.23967 (17)	0.42582 (11)	0.02890 (11)	0.0121 (3)
C7	0.23803 (17)	0.50275 (12)	−0.05091 (12)	0.0120 (2)
C8	0.21047 (17)	0.55767 (12)	−0.21278 (11)	0.0130 (3)
C9	0.17985 (19)	0.56017 (13)	−0.33573 (12)	0.0166 (3)
H9	0.1431	0.4777	−0.4155	0.020*
C10	0.20643 (19)	0.69051 (13)	−0.33395 (12)	0.0179 (3)
H10	0.1872	0.6949	−0.4142	0.021*
C11	0.19577 (18)	0.20677 (12)	0.04230 (12)	0.0150 (3)
H11	0.1628	0.1092	0.0003	0.018*
C12	0.19151 (18)	0.27840 (12)	−0.03356 (12)	0.0147 (3)
H12	0.1567	0.2286	−0.1260	0.018*
C13	0.26809 (17)	0.68429 (12)	−0.09392 (11)	0.0124 (3)
C14	0.29457 (18)	0.81564 (12)	−0.09143 (12)	0.0155 (3)
H14	0.3323	0.8983	−0.0118	0.019*
C15	0.26175 (18)	0.81641 (13)	−0.21382 (13)	0.0170 (3)
H15	0.2765	0.9017	−0.2167	0.020*

	U11	U22	U33	U12	U13	U23
O1	0.0222 (5)	0.0159 (4)	0.0151 (4)	0.0054 (3)	0.0048 (3)	0.0102 (3)
O5	0.0233 (5)	0.0193 (5)	0.0160 (5)	0.0049 (4)	0.0007 (4)	0.0066 (4)
O3	0.0199 (5)	0.0138 (4)	0.0189 (4)	0.0043 (3)	0.0029 (4)	0.0084 (3)
O2	0.0231 (5)	0.0140 (4)	0.0194 (4)	0.0053 (3)	0.0041 (4)	0.0101 (4)
O4	0.0223 (5)	0.0161 (4)	0.0179 (5)	0.0009 (4)	0.0056 (4)	0.0035 (4)
N1	0.0130 (5)	0.0139 (5)	0.0146 (5)	0.0040 (4)	0.0029 (4)	0.0084 (4)
N2	0.0135 (5)	0.0127 (5)	0.0118 (5)	0.0036 (4)	0.0025 (4)	0.0069 (4)
C1	0.0306 (7)	0.0214 (6)	0.0178 (6)	0.0076 (5)	0.0067 (5)	0.0146 (5)
C2	0.0113 (5)	0.0154 (5)	0.0165 (6)	0.0045 (4)	0.0041 (4)	0.0093 (5)
C3	0.0103 (5)	0.0148 (6)	0.0169 (6)	0.0049 (4)	0.0039 (4)	0.0102 (5)
C4	0.0167 (6)	0.0147 (6)	0.0130 (5)	0.0047 (4)	0.0037 (4)	0.0069 (4)
C5	0.0158 (6)	0.0121 (5)	0.0170 (6)	0.0044 (4)	0.0038 (4)	0.0078 (4)
C6	0.0094 (5)	0.0142 (5)	0.0160 (6)	0.0049 (4)	0.0038 (4)	0.0093 (5)
C7	0.0089 (5)	0.0131 (5)	0.0156 (5)	0.0040 (4)	0.0026 (4)	0.0080 (4)
C8	0.0108 (5)	0.0140 (5)	0.0155 (6)	0.0043 (4)	0.0028 (4)	0.0080 (4)
C9	0.0162 (6)	0.0196 (6)	0.0147 (6)	0.0051 (4)	0.0030 (4)	0.0090 (5)
C10	0.0162 (6)	0.0245 (6)	0.0178 (6)	0.0062 (5)	0.0035 (5)	0.0144 (5)
C11	0.0163 (6)	0.0121 (5)	0.0176 (6)	0.0047 (4)	0.0038 (5)	0.0080 (5)
C12	0.0162 (6)	0.0143 (5)	0.0130 (5)	0.0045 (4)	0.0022 (4)	0.0066 (4)
C13	0.0097 (5)	0.0161 (5)	0.0144 (5)	0.0045 (4)	0.0029 (4)	0.0095 (4)
C14	0.0143 (6)	0.0151 (6)	0.0189 (6)	0.0045 (4)	0.0042 (4)	0.0094 (5)
C15	0.0147 (6)	0.0183 (6)	0.0239 (6)	0.0053 (4)	0.0052 (5)	0.0150 (5)

O1—C2	1.3391 (14)	C4—C5	1.3904 (16)
O1—C1	1.4448 (14)	C4—H4	0.9300
O5—H21	0.88 (2)	C5—C6	1.4015 (16)
O5—H20	0.88 (2)	C5—H5	0.9300
O3—H17	0.952 (19)	C6—C12	1.4049 (16)
O3—H16	0.875 (19)	C6—C7	1.4754 (15)
O2—C2	1.2197 (14)	C8—C9	1.4021 (16)
O4—H19	0.88 (2)	C8—C13	1.4058 (16)
O4—H18	0.87 (2)	C9—C10	1.3882 (16)
N1—C7	1.3321 (15)	C9—H9	0.9300
N1—C8	1.3953 (14)	C10—C15	1.4102 (18)
N2—C7	1.3638 (14)	C10—H10	0.9300
N2—C13	1.3810 (14)	C11—C12	1.3885 (16)
N2—H2	0.8600	C11—H11	0.9300
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.3956 (15)
C1—H1C	0.9600	C14—C15	1.3864 (17)
C2—C3	1.4873 (15)	C14—H14	0.9300
C3—C11	1.3966 (16)	C15—H15	0.9300
C3—C4	1.3978 (16)
C2—O1—C1	116.02 (9)	C12—C6—C7	120.53 (10)
H21—O5—H20	101.8 (17)	N1—C7—N2	112.56 (10)
H17—O3—H16	107.0 (16)	N1—C7—C6	125.68 (10)
H19—O4—H18	101.0 (17)	N2—C7—C6	121.76 (10)
C7—N1—C8	104.98 (9)	N1—C8—C9	130.49 (11)
C7—N2—C13	107.37 (9)	N1—C8—C13	109.61 (10)
C7—N2—H2	126.3	C9—C8—C13	119.89 (10)
C13—N2—H2	126.3	C10—C9—C8	117.47 (11)
O1—C1—H1A	109.5	C10—C9—H9	121.3
O1—C1—H1B	109.5	C8—C9—H9	121.3
H1A—C1—H1B	109.5	C9—C10—C15	121.84 (11)
O1—C1—H1C	109.5	C9—C10—H10	119.1
H1A—C1—H1C	109.5	C15—C10—H10	119.1
H1B—C1—H1C	109.5	C12—C11—C3	120.47 (11)
O2—C2—O1	123.50 (11)	C12—C11—H11	119.8
O2—C2—C3	123.61 (11)	C3—C11—H11	119.8
O1—C2—C3	112.89 (10)	C11—C12—C6	120.20 (11)
C11—C3—C4	119.73 (10)	C11—C12—H12	119.9
C11—C3—C2	118.94 (10)	C6—C12—H12	119.9
C4—C3—C2	121.31 (11)	N2—C13—C14	131.59 (11)
C5—C4—C3	119.82 (11)	N2—C13—C8	105.47 (10)
C5—C4—H4	120.1	C14—C13—C8	122.93 (11)
C3—C4—H4	120.1	C15—C14—C13	116.52 (11)
C4—C5—C6	120.82 (11)	C15—C14—H14	121.7
C4—C5—H5	119.6	C13—C14—H14	121.7
C6—C5—H5	119.6	C14—C15—C10	121.34 (11)
C5—C6—C12	118.95 (10)	C14—C15—H15	119.3
C5—C6—C7	120.52 (10)	C10—C15—H15	119.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.86	1.99	2.8230 (13)	163
O4—H18···O3	0.87 (2)	1.92 (2)	2.7830 (13)	170.1 (17)
O3—H16···O2i	0.875 (19)	1.910 (19)	2.7840 (12)	177.4 (17)
O3—H17···O5ii	0.952 (19)	1.745 (19)	2.6932 (13)	173.9 (16)
O4—H19···N1iii	0.88 (2)	1.89 (2)	2.7614 (14)	171.0 (18)
O5—H20···O4iv	0.88 (2)	1.95 (2)	2.8291 (14)	174.0 (18)
O5—H21···O4v	0.88 (2)	1.90 (2)	2.7679 (13)	168.7 (18)
C15—H15···O5vi	0.93	2.59	3.4009 (15)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.86	1.99	2.8230 (13)	163
O4—H18⋯O3	0.87 (2)	1.92 (2)	2.7830 (13)	170.1 (17)
O3—H16⋯O2i	0.875 (19)	1.910 (19)	2.7840 (12)	177.4 (17)
O3—H17⋯O5ii	0.952 (19)	1.745 (19)	2.6932 (13)	173.9 (16)
O4—H19⋯N1iii	0.88 (2)	1.89 (2)	2.7614 (14)	171.0 (18)
O5—H20⋯O4iv	0.88 (2)	1.95 (2)	2.8291 (14)	174.0 (18)
O5—H21⋯O4v	0.88 (2)	1.90 (2)	2.7679 (13)	168.7 (18)
C15—H15⋯O5vi	0.93	2.59	3.4009 (15)	146

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