Crystal structure of benzimidazolium salicylate.

In the anion of the title mol-ecular salt, C7H7N2 (+)·C7H5O3 (-) (systematic name: 1H-benzimidazol-3-ium 2-hy-droxy-ben-zo-ate), there is an intra-molecular O-H⋯O hydrogen bond that generates an S(6) ring motif. The CO2 group makes a dihedral angle of 5.33 (15)° with its attached ring. In the crystal, the dihedral angle between the benzimidazolium ring and the anion benzene ring is 75.88 (5)°. Two cations bridge two anions via two pairs of N-H⋯O hydrogen bonds, enclosing an R (4) 4(16) ring motif, forming a four-membered centrosymmetric arrangement. These units are linked via C-H⋯O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked by C-H⋯π and π-π inter-actions [inter-centroid distances = 3.4156 (7) and 3.8196 (8) Å], forming a three-dimensional structure.

Related literature

For biological applications of benzimidazole derivatives, see: Narasimhan et al. (2012 ▸). For related structures, see: Ennajih et al. (2010 ▸); Haque et al. (2012 ▸); Mani et al. (2015 ▸).

Experimental

Crystal data

C7H7N2 +·C7H5O3 −

M = 256.26

Monoclinic,

a = 7.4776 (3) Å

b = 6.7002 (2) Å

c = 24.9017 (9) Å

β = 94.445 (2)°

V = 1243.86 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.34 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.967, T max = 0.976

23125 measured reflections

4606 independent reflections

3020 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 1.03

4606 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015017764/su5212sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017764/su5212Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017764/su5212Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015017764/su5212fig1.tif

The mol­ecular structure of the title salt, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015017764/su5212fig2.tif

The crystal packing of the title mol­ecular salt, viewed along the b axis. The N—H⋯O and C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1). H atoms not involved in these inter­actions have been omitted for clarity.

CCDC reference: 1426331

Additional supporting information: crystallographic information; 3D view; checkCIF report

C7H7N2+·C7H5O3−	F(000) = 536
Mr = 256.26	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8207 reflections
a = 7.4776 (3) Å	θ = 2.7–31.0°
b = 6.7002 (2) Å	µ = 0.10 mm−1
c = 24.9017 (9) Å	T = 295 K
β = 94.445 (2)°	Block, colourless
V = 1243.86 (8) Å3	0.34 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4606 independent reflections
Radiation source: fine-focus sealed tube	3020 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scan	θmax = 39.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.967, Tmax = 0.976	k = −11→9
23125 measured reflections	l = −35→35

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.2364P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4606 reflections	Δρmax = 0.35 e Å−3
176 parameters	Δρmin = −0.26 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.85922 (14)	0.54826 (15)	0.16407 (4)	0.0321 (2)
C2	0.94451 (17)	0.73153 (18)	0.17277 (5)	0.0414 (3)
H2	1.0347	0.7692	0.1511	0.050*
C3	0.8971 (2)	0.8581 (2)	0.21304 (5)	0.0499 (3)
H3	0.9554	0.9798	0.2187	0.060*
C4	0.76260 (19)	0.8026 (2)	0.24480 (5)	0.0503 (3)
H4	0.7296	0.8882	0.2717	0.060*
C5	0.67701 (18)	0.6234 (2)	0.23729 (5)	0.0475 (3)
H5	0.5866	0.5878	0.2591	0.057*
C6	0.72508 (16)	0.49396 (18)	0.19710 (4)	0.0391 (3)
C7	0.91104 (17)	0.41505 (16)	0.12000 (4)	0.0375 (2)
C8	1.27512 (15)	1.05724 (17)	0.05515 (5)	0.0381 (2)
C9	1.3448 (2)	1.0252 (2)	0.10764 (6)	0.0562 (4)
H9	1.3355	1.1203	0.1345	0.067*
C10	1.4287 (2)	0.8448 (3)	0.11783 (7)	0.0697 (5)
H10	1.4781	0.8180	0.1525	0.084*
C11	1.4420 (2)	0.7016 (3)	0.07804 (8)	0.0659 (4)
H11	1.4981	0.5810	0.0870	0.079*
C12	1.37525 (18)	0.7325 (2)	0.02618 (6)	0.0516 (3)
H12	1.3854	0.6367	−0.0004	0.062*
C13	1.29132 (15)	0.91474 (16)	0.01517 (5)	0.0371 (2)
C14	1.14314 (16)	1.17020 (18)	−0.02020 (5)	0.0409 (3)
H14	1.0797	1.2524	−0.0450	0.049*
N1	1.18155 (14)	1.21523 (14)	0.03109 (4)	0.0398 (2)
H1A	1.1532	1.3239	0.0467	0.048*
N2	1.20728 (13)	0.99240 (14)	−0.03137 (4)	0.0400 (2)
H2A	1.1981	0.9351	−0.0624	0.048*
O1	1.02203 (14)	0.47695 (13)	0.08885 (4)	0.0521 (3)
O2	0.83774 (17)	0.24546 (14)	0.11610 (4)	0.0613 (3)
O3	0.63621 (17)	0.31901 (17)	0.19135 (4)	0.0653 (3)
H3A	0.680 (3)	0.261 (3)	0.1658 (7)	0.098*

	U11	U22	U33	U12	U13	U23
C1	0.0371 (5)	0.0327 (5)	0.0266 (4)	0.0025 (4)	0.0035 (4)	−0.0024 (4)
C2	0.0442 (6)	0.0390 (6)	0.0411 (6)	−0.0041 (5)	0.0050 (5)	−0.0034 (4)
C3	0.0594 (8)	0.0395 (6)	0.0497 (7)	−0.0019 (6)	−0.0034 (6)	−0.0137 (5)
C4	0.0556 (7)	0.0559 (8)	0.0389 (6)	0.0139 (6)	0.0004 (5)	−0.0169 (5)
C5	0.0454 (6)	0.0626 (8)	0.0357 (6)	0.0047 (6)	0.0106 (5)	−0.0078 (5)
C6	0.0413 (6)	0.0431 (6)	0.0334 (5)	−0.0024 (5)	0.0065 (4)	−0.0031 (4)
C7	0.0508 (6)	0.0334 (5)	0.0290 (5)	0.0041 (4)	0.0074 (4)	−0.0012 (4)
C8	0.0342 (5)	0.0409 (6)	0.0400 (6)	−0.0039 (4)	0.0077 (4)	−0.0050 (4)
C9	0.0551 (8)	0.0698 (9)	0.0426 (7)	−0.0019 (7)	−0.0021 (6)	−0.0076 (6)
C10	0.0627 (9)	0.0871 (12)	0.0566 (9)	0.0073 (9)	−0.0127 (7)	0.0111 (8)
C11	0.0541 (8)	0.0583 (9)	0.0838 (11)	0.0114 (7)	−0.0049 (8)	0.0125 (8)
C12	0.0431 (7)	0.0421 (6)	0.0701 (9)	0.0045 (5)	0.0083 (6)	−0.0051 (6)
C13	0.0321 (5)	0.0367 (5)	0.0433 (6)	−0.0031 (4)	0.0089 (4)	−0.0040 (4)
C14	0.0436 (6)	0.0393 (6)	0.0409 (6)	−0.0013 (5)	0.0113 (5)	0.0021 (4)
N1	0.0439 (5)	0.0342 (5)	0.0426 (5)	−0.0009 (4)	0.0119 (4)	−0.0064 (4)
N2	0.0454 (5)	0.0404 (5)	0.0354 (5)	−0.0036 (4)	0.0100 (4)	−0.0066 (4)
O1	0.0708 (6)	0.0415 (5)	0.0480 (5)	0.0047 (4)	0.0301 (4)	−0.0018 (4)
O2	0.0956 (8)	0.0428 (5)	0.0487 (5)	−0.0176 (5)	0.0264 (5)	−0.0168 (4)
O3	0.0751 (7)	0.0598 (6)	0.0656 (7)	−0.0275 (5)	0.0340 (5)	−0.0142 (5)

C1—C2	1.3929 (16)	C8—C13	1.3913 (16)
C1—C6	1.3939 (15)	C9—C10	1.376 (2)
C1—C7	1.4889 (14)	C9—H9	0.9300
C2—C3	1.3803 (17)	C10—C11	1.388 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.378 (2)	C11—C12	1.364 (2)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.367 (2)	C12—C13	1.3902 (17)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.3922 (16)	C13—N2	1.3769 (15)
C5—H5	0.9300	C14—N2	1.3219 (15)
C6—O3	1.3496 (15)	C14—N1	1.3220 (15)
C7—O1	1.2499 (14)	C14—H14	0.9300
C7—O2	1.2620 (14)	N1—H1A	0.8600
C8—N1	1.3798 (15)	N2—H2A	0.8600
C8—C9	1.3861 (18)	O3—H3A	0.834 (9)
C2—C1—C6	118.68 (10)	C10—C9—H9	121.9
C2—C1—C7	120.07 (10)	C8—C9—H9	121.9
C6—C1—C7	121.25 (10)	C9—C10—C11	122.17 (14)
C3—C2—C1	120.96 (12)	C9—C10—H10	118.9
C3—C2—H2	119.5	C11—C10—H10	118.9
C1—C2—H2	119.5	C12—C11—C10	121.97 (14)
C4—C3—C2	119.41 (12)	C12—C11—H11	119.0
C4—C3—H3	120.3	C10—C11—H11	119.0
C2—C3—H3	120.3	C11—C12—C13	116.52 (13)
C5—C4—C3	120.90 (11)	C11—C12—H12	121.7
C5—C4—H4	119.5	C13—C12—H12	121.7
C3—C4—H4	119.5	N2—C13—C12	131.86 (11)
C4—C5—C6	120.08 (12)	N2—C13—C8	106.47 (10)
C4—C5—H5	120.0	C12—C13—C8	121.64 (12)
C6—C5—H5	120.0	N2—C14—N1	110.72 (11)
O3—C6—C5	117.70 (11)	N2—C14—H14	124.6
O3—C6—C1	122.34 (10)	N1—C14—H14	124.6
C5—C6—C1	119.96 (11)	C14—N1—C8	108.01 (10)
O1—C7—O2	123.80 (10)	C14—N1—H1A	126.0
O1—C7—C1	118.80 (10)	C8—N1—H1A	126.0
O2—C7—C1	117.40 (10)	C14—N2—C13	108.22 (10)
N1—C8—C9	132.02 (11)	C14—N2—H2A	125.9
N1—C8—C13	106.57 (10)	C13—N2—H2A	125.9
C9—C8—C13	121.41 (12)	C6—O3—H3A	105.2 (16)
C10—C9—C8	116.28 (14)
C6—C1—C2—C3	−0.37 (17)	C13—C8—C9—C10	−0.6 (2)
C7—C1—C2—C3	179.30 (11)	C8—C9—C10—C11	−0.5 (2)
C1—C2—C3—C4	−0.42 (19)	C9—C10—C11—C12	1.1 (3)
C2—C3—C4—C5	0.6 (2)	C10—C11—C12—C13	−0.6 (2)
C3—C4—C5—C6	−0.1 (2)	C11—C12—C13—N2	−178.38 (13)
C4—C5—C6—O3	−179.93 (12)	C11—C12—C13—C8	−0.51 (19)
C4—C5—C6—C1	−0.75 (19)	N1—C8—C13—N2	0.10 (12)
C2—C1—C6—O3	−179.91 (12)	C9—C8—C13—N2	179.49 (11)
C7—C1—C6—O3	0.42 (18)	N1—C8—C13—C12	−178.25 (11)
C2—C1—C6—C5	0.96 (17)	C9—C8—C13—C12	1.14 (18)
C7—C1—C6—C5	−178.71 (11)	N2—C14—N1—C8	−0.50 (13)
C2—C1—C7—O1	−5.18 (17)	C9—C8—N1—C14	−179.06 (14)
C6—C1—C7—O1	174.49 (11)	C13—C8—N1—C14	0.23 (13)
C2—C1—C7—O2	175.54 (12)	N1—C14—N2—C13	0.56 (13)
C6—C1—C7—O2	−4.79 (17)	C12—C13—N2—C14	177.72 (13)
N1—C8—C9—C10	178.60 (14)	C8—C13—N2—C14	−0.40 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.83 (1)	1.78 (1)	2.5425 (14)	152 (2)
N1—H1A···O1i	0.86	1.81	2.6139 (13)	155
N2—H2A···O2ii	0.86	1.81	2.6448 (13)	164
C14—H14···O1iii	0.93	2.22	3.1161 (16)	161
C3—H3···Cg3iv	0.93	2.81	3.5779 (15)	141
C10—H10···Cg3v	0.93	2.88	3.6302 (17)	139

Table 1

Hydrogen-bond geometry (, )

Cg3 is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
O3H3AO2	0.83(1)	1.78(1)	2.5425(14)	152(2)
N1H1AO1i	0.86	1.81	2.6139(13)	155
N2H2AO2ii	0.86	1.81	2.6448(13)	164
C14H14O1iii	0.93	2.22	3.1161(16)	161
C3H3Cg3iv	0.93	2.81	3.5779(15)	141
C10H10Cg3v	0.93	2.88	3.6302(17)	139

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