A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid

Kuai, H.-W.

doi:10.1107/S1600536812041025

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3068

doi:10.1107/S1600536812041025

Open

access

A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid

Hai-Wei Kuai ^a ^*

^aFaculty of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, People's Republic of China
^*Correspondence e-mail: hyitshy@126.com

(Received 22 September 2012; accepted 29 September 2012; online 6 October 2012)

Crystals of the title compound, C₁₆H₁₂N₂O₄, were obtained accidentally by the hydrothermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)methyl]isophthalic acid with manganese chloride tetrahydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this structure has been reported previously from a similar reaction [Cheng (2011 ). Acta Cryst. E67, o3299]. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.020 (4) Å. The benzimidazole unit and benzene ring are inclined at a dihedral angle of 68.17 (4)°, reflecting the axial rotation of the flexible benzimidazolyl arm. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent molecules into inversion dimers. O—H⋯N contacts connect these dimers into zigzag chains along [010].

Related literature

For a triclinic polymorph of the title compound, see: Cheng (2011).

Experimental

Crystal data

C₁₆H₁₂N₂O₄
M_r = 296.28
Monoclinic, P 2₁ /c
a = 7.401 (5) Å
b = 16.589 (5) Å
c = 11.762 (4) Å
β = 111.53 (3)°
V = 1343.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker Smart APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.989
6722 measured reflections
2358 independent reflections
1239 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.152
S = 0.96
2358 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H5⋯O4ⁱ	0.84	1.82	2.649 (3)	171
O1—H4⋯N1ⁱⁱ	0.84	1.76	2.576 (4)	164
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x-1, y, z-1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812041025/sj5265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041025/sj5265Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812041025/sj5265Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812041025/sj5265Isup4.cml

checkCIF report

Comment top

5-((1H-benzo[d]imidazol-1-yl)methyl)isophthalic acid (H₂L), is usually regarded as an excellent candidate for use as a building block in molecular self-assembly engineerings due to its variable conformations and coordination modes. During an attempt to assemble a coordination polymer, we accidentally obtained some single crystals of the title compound, C₁₆H₁₂N₂O₄, as a result of the hydrothermal reaction of 5-((1H-benzo[d]imidazol-1-yl)methyl)isophthalic acid with manganese chloride tetrahydrate at 453 K in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this structure has been reported previously (Cheng, 2011) from a very similar hydrothermal reaction involving manganese bromide. The bond distances and angles in that molecule are reasonably similar to those reported here. As shown in Fig. 1, the asymmetric unit consists of only one H₂L molecule. Interestingly, though crystallizing from alkaline solution, the H₂L retains the intact carboxylic acid groups in the crystal structure. The flexible benzimidazolyl arm is apt to rotate axially. As a result, the benzimidazolyl ring and central benzene rings are inclined at a dihedral angle of 68.17 °.

In the crystal structure O3–H5..O4 hydrogen bonds, Table 1, link adjacent molecules into inversion dimers. O1—H4···N1 contacts connect these dimers into zig-zag chains in the 010 plane, Fig. 2.

Related literature top

For a triclinic polymorph of the title compound, see: Cheng (2011).

Experimental top

A reaction mixture comprising manganese chloride tetrahydrate (23.3 mg, 0.1 mmol), 5-((1H-benzo[d]imidazol-1-yl)methyl)isophthalic acid (29.6 mg, 0.1 mmol) and KOH (11.2 mg, 0.2 mmol) in 10 ml H₂O was sealed in a 16 ml Teflon-lined stainless steel container and heated to 453 K for 3 days. After cooling to the room temperature, colorless block like crystals of the title compound were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : The crystal structure of the title compound showing 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound.

5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid top

Crystal data top

C₁₆H₁₂N₂O₄	F(000) = 616
M_r = 296.28	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 479 reflections
a = 7.401 (5) Å	θ = 2.2–18.5°
b = 16.589 (5) Å	µ = 0.11 mm⁻¹
c = 11.762 (4) Å	T = 293 K
β = 111.53 (3)°	Block, colorless
V = 1343.3 (11) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker Smart APEXII CCD diffractometer	2358 independent reflections
Radiation source: fine-focus sealed tube	1239 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→6
T_min = 0.979, T_max = 0.989	k = −19→19
6722 measured reflections	l = −13→13

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)] = 0.056	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.0659P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
2358 reflections	Δρ_max = 0.21 e Å⁻³
200 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (15)

Crystal data top

C₁₆H₁₂N₂O₄	V = 1343.3 (11) Å³
M_r = 296.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.401 (5) Å	µ = 0.11 mm⁻¹
b = 16.589 (5) Å	T = 293 K
c = 11.762 (4) Å	0.20 × 0.10 × 0.10 mm
β = 111.53 (3)°

Data collection top

Bruker Smart APEXII CCD diffractometer	2358 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1239 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.989	R_int = 0.072
6722 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 0.96	Δρ_max = 0.21 e Å⁻³
2358 reflections	Δρ_min = −0.22 e Å⁻³
200 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.4929 (4)	0.81173 (19)	0.6457 (3)	0.0337 (8)
C2	0.3157 (4)	0.81097 (19)	0.5499 (3)	0.0359 (8)
H1	0.2128	0.7828	0.5586	0.043*
C3	0.2869 (4)	0.85118 (19)	0.4407 (3)	0.0334 (8)
C4	0.4398 (4)	0.89389 (18)	0.4285 (3)	0.0322 (8)
H2	0.4224	0.9211	0.3561	0.039*
C5	0.6190 (4)	0.89614 (19)	0.5242 (3)	0.0335 (8)
C6	0.6444 (4)	0.85508 (19)	0.6319 (3)	0.0369 (8)
H3	0.7645	0.8566	0.6957	0.044*
C11	0.5228 (4)	0.7621 (2)	0.7587 (2)	0.0393 (9)
H7	0.4032	0.7336	0.7480	0.047*
H6	0.6222	0.7220	0.7666	0.047*
C12	0.7566 (4)	0.8106 (2)	0.9604 (3)	0.0419 (9)
H8	0.8643	0.7849	0.9542	0.050*
C13	0.5734 (5)	0.87902 (19)	1.0306 (3)	0.0391 (9)
C14	0.4574 (4)	0.85280 (19)	0.9137 (3)	0.0359 (8)
C15	0.2615 (5)	0.8708 (2)	0.8615 (3)	0.0526 (10)
H9	0.1855	0.8535	0.7833	0.063*
C16	0.1854 (6)	0.9155 (2)	0.9315 (4)	0.0641 (11)
H10	0.0545	0.9293	0.8993	0.077*
C17	0.2977 (6)	0.9410 (2)	1.0494 (4)	0.0616 (11)
H11	0.2394	0.9698	1.0945	0.074*
C18	0.4931 (5)	0.9243 (2)	1.1002 (3)	0.0529 (10)
H12	0.5688	0.9424	1.1780	0.063*
C31	0.0929 (5)	0.8454 (2)	0.3395 (3)	0.0421 (9)
C51	0.7854 (5)	0.9411 (2)	0.5135 (3)	0.0393 (8)
N1	0.7629 (4)	0.85258 (17)	1.0568 (2)	0.0451 (8)
N2	0.5798 (3)	0.80875 (16)	0.8720 (2)	0.0363 (7)
O1	0.0865 (3)	0.87513 (17)	0.23681 (19)	0.0661 (8)
H4	−0.0285	0.8693	0.1880	0.079*
O2	−0.0442 (3)	0.81489 (18)	0.3545 (2)	0.0756 (9)
O3	0.7501 (3)	0.97884 (14)	0.41101 (19)	0.0493 (7)
H5	0.8528	1.0018	0.4151	0.059*
O4	0.9450 (3)	0.94199 (15)	0.5985 (2)	0.0584 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0290 (18)	0.043 (2)	0.0258 (17)	−0.0006 (16)	0.0059 (15)	0.0014 (15)
C2	0.0313 (18)	0.041 (2)	0.0351 (18)	−0.0055 (15)	0.0113 (15)	−0.0018 (16)
C3	0.0288 (18)	0.040 (2)	0.0296 (17)	0.0005 (15)	0.0088 (14)	0.0001 (16)
C4	0.0318 (18)	0.037 (2)	0.0259 (16)	−0.0018 (15)	0.0086 (15)	−0.0012 (15)
C5	0.0295 (18)	0.040 (2)	0.0282 (17)	−0.0039 (15)	0.0077 (15)	−0.0017 (15)
C6	0.0283 (19)	0.047 (2)	0.0283 (17)	−0.0037 (16)	0.0022 (15)	−0.0040 (16)
C11	0.0355 (19)	0.046 (2)	0.0304 (17)	−0.0040 (16)	0.0052 (15)	0.0010 (17)
C12	0.033 (2)	0.054 (2)	0.0341 (19)	0.0039 (17)	0.0064 (16)	0.0062 (18)
C13	0.037 (2)	0.047 (2)	0.0307 (18)	−0.0021 (17)	0.0093 (16)	0.0076 (17)
C14	0.0298 (19)	0.044 (2)	0.0327 (18)	−0.0008 (16)	0.0096 (15)	0.0020 (16)
C15	0.040 (2)	0.067 (3)	0.049 (2)	−0.0017 (19)	0.0143 (19)	0.007 (2)
C16	0.048 (2)	0.076 (3)	0.074 (3)	0.008 (2)	0.029 (2)	0.012 (2)
C17	0.063 (3)	0.065 (3)	0.071 (3)	0.014 (2)	0.042 (2)	0.008 (2)
C18	0.070 (3)	0.054 (3)	0.039 (2)	−0.003 (2)	0.026 (2)	−0.0002 (18)
C31	0.033 (2)	0.052 (2)	0.034 (2)	−0.0013 (17)	0.0048 (17)	0.0042 (18)
C51	0.035 (2)	0.050 (2)	0.0307 (18)	−0.0049 (17)	0.0092 (17)	−0.0014 (17)
N1	0.0376 (17)	0.059 (2)	0.0304 (15)	0.0002 (14)	0.0031 (13)	0.0004 (15)
N2	0.0275 (15)	0.0483 (18)	0.0257 (14)	−0.0005 (13)	0.0011 (12)	0.0013 (13)
O1	0.0401 (15)	0.115 (2)	0.0312 (13)	−0.0222 (14)	−0.0014 (12)	0.0127 (15)
O2	0.0357 (15)	0.123 (3)	0.0534 (16)	−0.0303 (15)	−0.0005 (13)	0.0262 (16)
O3	0.0402 (14)	0.0641 (17)	0.0421 (14)	−0.0163 (12)	0.0134 (11)	0.0060 (13)
O4	0.0310 (14)	0.088 (2)	0.0449 (14)	−0.0173 (13)	0.0008 (12)	0.0130 (14)

Geometric parameters (Å, º) top

C1—C2	1.380 (4)	C13—N1	1.392 (4)
C1—C6	1.390 (4)	C13—C18	1.394 (4)
C1—C11	1.510 (4)	C13—C14	1.397 (4)
C2—C3	1.393 (4)	C14—C15	1.384 (4)
C2—H1	0.9300	C14—N2	1.386 (4)
C3—C4	1.386 (4)	C15—C16	1.374 (5)
C3—C31	1.494 (4)	C15—H9	0.9300
C4—C5	1.390 (4)	C16—C17	1.395 (5)
C4—H2	0.9300	C16—H10	0.9300
C5—C6	1.389 (4)	C17—C18	1.375 (5)
C5—C51	1.484 (4)	C17—H11	0.9300
C6—H3	0.9300	C18—H12	0.9300
C11—N2	1.463 (4)	C31—O2	1.203 (4)
C11—H7	0.9700	C31—O1	1.289 (4)
C11—H6	0.9700	C51—O4	1.236 (3)
C12—N1	1.317 (4)	C51—O3	1.297 (3)
C12—N2	1.340 (4)	O1—H4	0.8397
C12—H8	0.9300	O3—H5	0.8356

C2—C1—C6	118.4 (3)	C18—C13—C14	120.4 (3)
C2—C1—C11	120.1 (3)	C15—C14—N2	132.1 (3)
C6—C1—C11	121.4 (3)	C15—C14—C13	122.3 (3)
C1—C2—C3	121.7 (3)	N2—C14—C13	105.5 (3)
C1—C2—H1	119.1	C16—C15—C14	116.3 (3)
C3—C2—H1	119.1	C16—C15—H9	121.8
C4—C3—C2	119.1 (3)	C14—C15—H9	121.8
C4—C3—C31	122.2 (3)	C15—C16—C17	122.3 (4)
C2—C3—C31	118.8 (3)	C15—C16—H10	118.9
C3—C4—C5	120.2 (3)	C17—C16—H10	118.9
C3—C4—H2	119.9	C18—C17—C16	121.2 (4)
C5—C4—H2	119.9	C18—C17—H11	119.4
C6—C5—C4	119.6 (3)	C16—C17—H11	119.4
C6—C5—C51	119.1 (3)	C17—C18—C13	117.4 (3)
C4—C5—C51	121.3 (3)	C17—C18—H12	121.3
C5—C6—C1	121.0 (3)	C13—C18—H12	121.3
C5—C6—H3	119.5	O2—C31—O1	123.7 (3)
C1—C6—H3	119.5	O2—C31—C3	121.7 (3)
N2—C11—C1	114.4 (3)	O1—C31—C3	114.6 (3)
N2—C11—H7	108.7	O4—C51—O3	123.6 (3)
C1—C11—H7	108.7	O4—C51—C5	120.9 (3)
N2—C11—H6	108.7	O3—C51—C5	115.6 (3)
C1—C11—H6	108.7	C12—N1—C13	105.2 (3)
H7—C11—H6	107.6	C12—N2—C14	107.0 (3)
N1—C12—N2	113.4 (3)	C12—N2—C11	126.3 (3)
N1—C12—H8	123.3	C14—N2—C11	126.4 (3)
N2—C12—H8	123.3	C31—O1—H4	106.1
N1—C13—C18	130.7 (3)	C51—O3—H5	107.3
N1—C13—C14	109.0 (3)

C6—C1—C2—C3	1.0 (5)	C16—C17—C18—C13	−1.7 (5)
C11—C1—C2—C3	−175.2 (3)	N1—C13—C18—C17	−179.7 (3)
C1—C2—C3—C4	−0.8 (5)	C14—C13—C18—C17	0.4 (5)
C1—C2—C3—C31	178.0 (3)	C4—C3—C31—O2	−172.8 (3)
C2—C3—C4—C5	0.1 (5)	C2—C3—C31—O2	8.5 (5)
C31—C3—C4—C5	−178.6 (3)	C4—C3—C31—O1	7.6 (5)
C3—C4—C5—C6	0.3 (4)	C2—C3—C31—O1	−171.1 (3)
C3—C4—C5—C51	179.7 (3)	C6—C5—C51—O4	0.3 (5)
C4—C5—C6—C1	−0.1 (5)	C4—C5—C51—O4	−179.2 (3)
C51—C5—C6—C1	−179.6 (3)	C6—C5—C51—O3	−179.1 (3)
C2—C1—C6—C5	−0.5 (5)	C4—C5—C51—O3	1.5 (4)
C11—C1—C6—C5	175.6 (3)	N2—C12—N1—C13	1.3 (4)
C2—C1—C11—N2	−121.4 (3)	C18—C13—N1—C12	178.4 (3)
C6—C1—C11—N2	62.6 (4)	C14—C13—N1—C12	−1.7 (4)
N1—C13—C14—C15	−179.2 (3)	N1—C12—N2—C14	−0.5 (4)
C18—C13—C14—C15	0.7 (5)	N1—C12—N2—C11	−174.7 (3)
N1—C13—C14—N2	1.4 (3)	C15—C14—N2—C12	−179.9 (3)
C18—C13—C14—N2	−178.7 (3)	C13—C14—N2—C12	−0.6 (3)
N2—C14—C15—C16	178.6 (3)	C15—C14—N2—C11	−5.7 (5)
C13—C14—C15—C16	−0.6 (5)	C13—C14—N2—C11	173.6 (3)
C14—C15—C16—C17	−0.7 (5)	C1—C11—N2—C12	−106.8 (3)
C15—C16—C17—C18	1.9 (6)	C1—C11—N2—C14	80.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H5···O4ⁱ	0.84	1.82	2.649 (3)	171
O1—H4···N1ⁱⁱ	0.84	1.76	2.576 (4)	164

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₄
M_r	296.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.401 (5), 16.589 (5), 11.762 (4)
β (°)	111.53 (3)
V (Å³)	1343.3 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker Smart APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6722, 2358, 1239
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.152, 0.96
No. of reflections	2358
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H5···O4ⁱ	0.84	1.82	2.649 (3)	171.4
O1—H4···N1ⁱⁱ	0.84	1.76	2.576 (4)	164.1

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x−1, y, z−1.

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, wisconsin, USA. Google Scholar
Cheng, X.-C. (2011). Acta Cryst. E67, o3299. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3068

doi:10.1107/S1600536812041025

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­­oxy­lic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid