Crystal structure, Hirshfeld and electronic transition analysis of 2-[(1H-benzimidazol-1-yl)meth­yl]benzoic acid

Ali, A.; Muslim, M.; Kamaal, S.; Ahmed, A.; Ahmad, M.; Shahid, M.; Khan, J.A.; Dege, N.; Javed, S.; Mashrai, A.

doi:10.1107/S2056989021006435

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ISSN: 2056-9890

Volume 77| Part 7| July 2021| Pages 755-758

https://doi.org/10.1107/S2056989021006435

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Crystal structure, Hirshfeld and electronic transition analysis of 2-[(1H-benzimidazol-1-yl)methyl]benzoic acid

Arif Ali,^a Mohd Muslim,^a Saima Kamaal,^a Adeeba Ahmed,^a Musheer Ahmad,^a ^* M. Shahid,^b Jamal A. Khan,^a Necmi Dege,^c Saleem Javed ^d and Ashraf Mashrai ^e ^*

^aDepartment of Applied Chemistry, Faculty of Engineering and Technology, ZHCET, Aligarh Muslim University, Aligarh 202002 (UP), India, ^bFunctional Inorganic Materials Lab (FIML), Department of Chemistry, Aligarh, Muslim University, Aligarh 202002, India, ^cOndokuz Mayis University, Faculty of Arts and Sciences, Department of, Physics,55139 Samsun, Turkey, ^dDepartment of Chemistry, Institute of H. Science, Dr. Bhimrao Ambedkar, University, Agra 282002, U. P., India, and ^eDepartment of Pharmacy, University of Science and Technology, Ibb branch, Yemen
^*Correspondence e-mail: amusheer4@gmail.com, ashraf.yemen7@gmail.com

Edited by J. Ellena, Universidade de Sâo Paulo, Brazil (Received 15 April 2021; accepted 21 June 2021; online 30 June 2021)

In the title compound, C₁₅H₁₂N₂O₂, the benzimidazole ring system is inclined to the benzene ring by 78.04 (10)°. The crystal structure features O—H⋯N and C—H⋯O hydrogen bonding and C—H⋯π and π–π interactions, which were investigated using Hirshfeld surface analysis.

Keywords: crystal structure; benzimidazole; Tauc plot; Hirshfeld surface analysis.

CCDC reference: 2091351

1. Chemical context

Benzimidazole is a naturally ocurring compound, being present in vitamin B₁₂ (Crofts et al., 2014 ) and may also be synthesized from benzoic acid and o-phenylenediamine in presence of an excess of acid. Benzimidazole and its derivatives show biological activities such as antibacterial, antifungal (Yadav et al., 2015 ), antimicrobial (Shruthi et al., 2016 ), and anticancer (Kalalbandi et al., 2015 ). Cyanobenzyl compounds are used as intermediates in the synthesis of species that possess significant pharmaceutical properties. Compounds having carboxylic acid as a functional group have shown chelating properties and thus have potential applications in the field of biology. Such groups are also helpful in building metal–organic frameworks that usually form supramolecular networks due to extensive hydrogen bonding and weak interactions. For example, 4-[(1H-benzo[d]imidazol-1-yl)methyl]benzoic acid has been used to construct coordination polymers with different metal ions (Ahmad et al., 2013 ). Herein, we report the title compound, 2-[(1H-benzimidazol-1-yl)methyl]benzoic acid, which was synthesized by a condensation reaction of benzimidazole and 2-(bromomethyl) benzonitrile in acetonitrile followed by a hydrolysis process.

2. Structural commentary

The asymmetric unit of the title compound is illustrated in Fig. 1. The molecule is non-planar with a dihedral angle of 78.04 (10) between the benzimidazole ring system and the benzene ring. The N1—C8—C7 angle is 113.31° and the C9—N1—C8—C7 torsion angle is −116.8 (2)°,. The C10—C15 bond length [1.408 (3) Å] is comparable to that in a similar benzimidazole derivative (Faizi et al., 2017 ). The C—O bond lengths [C1—O1 = 1.319 (3) and C1—O2 = 1.216 (3) Å] are in the expected range (Kamaal et al., 2019 ).

Figure 1
Asymmetric unit of title compound, with atom labelling and displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal, the molecules are connected via O—H⋯N and C—H⋯O hydrogen bonds (Table 1), forming a 1D framework along the b-axis direction (Fig. 2). C—H⋯π and π–π interactions [centroid–centroid distance = 3.6166 (15) Å] between the N1/N2/C9/C10/C15 and C2–C7 rings also occur, leading to the formation of the supramolecular structure (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/N2/C9/C10/C15, C2–C7, C10–C15 and N1/N2/C9–15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.88 (3)	1.73 (3)	2.592 (3)	164 (4)
C8—H8A⋯O1ⁱⁱ	0.99 (1)	2.62 (1)	3.374 (3)	133 (1)
C4—H4⋯Cg1ⁱⁱⁱ	0.95 (1)	2.99 (1)	3.865 (3)	155 (1)
C4—H4⋯Cg3ⁱⁱⁱ	0.95 (1)	2.51 (1)	3.408 (3)	157 (1)
C4—H4⋯Cg4ⁱⁱⁱ	0.95 (1)	2.51 (1)	3.454 (3)	170 (1)
C5—H5⋯Cg2ⁱⁱⁱ	0.95 (1)	2.76 (1)	3.554 (3)	142 (1)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Figure 2
View of the crystal packing along the a axis, showing O—H⋯N and C—H⋯O hydrogen-bonding interactions forming a one-dimensional chain.

Figure 3
The hydrogen bonding and C—H⋯π and π–π interactions form zigzag chains, giving a supramolecular structure along the bc plane.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.42, November 2020; Groom et al., 2016 ) found five examples of similar compounds: bis(pentafluorophenyl)-(μ-{1,1′-[1,2-phenylenebis(methylene)]bis(1H-benzimidazole)})digold(I) acetone solvate (WOPLIZ; Zheng et al., 2019 ), 3,3′-[1,2-phenylenebis(methylene)]bis(1-ethylbenzimidazolium) dibromide (LANHAL; Haque et al., 2012 ), 2-[(1H-benzimidazol-1-yl)methyl]benzonitrile (JONYUJ; Akkoç et al., 2017 ), 1-[(2-cyanophenyl)methyl]-3-[(2-methylphenyl)methyl]-1H-benzimidazol-3-ium (JONZAQ; Akkoç et al., 2017) and 1-(2-cyanobenzyl)-3-methyl-1H-3,1-benzimidazol-3-ium bromide (MOCWAE; Ghdhayeb et al., 2014 ).

5. Hirshfeld surface analysis

A Hirshfeld surface analysis was performed and the two-dimensional fingerprint plots generated (McKinnon et al., 2007 ; Spackman & Jayatilaka et al., 2009 ) using CrystalExplorer17 (Turner et al., 2017 ). The Hirshfeld surface mapped over d_norm, colour-mapped from red (shorter distance than the sum of van der Waals radii) through white to blue (longer distance than the sum of the van der Waals radii). The principal weak interactions are clearly visible. The surface coverage corresponding to O—H⋯N and C—H⋯O interactions are 9% and 11.8%, respectively. The dark-red spot indicates significant hydrogen bonding.

The two-dimensional finger plots are given in Fig. 4. The principal contributions to the overall surface are from H⋯H (42.4%, Fig. 4b), C⋯H/H⋯C (27.4%, Fig. 4c) and N⋯H/H⋯N 9% (Fig. 4d) interactions. The contributions of interactions such as C⋯C 4.8% are negligible.

Figure 4
The Hirshfeld surface of the title compound mapped over d_norm, in the range −0.722 to 1.183. (a) The overall two-dimensional finger plot of the title compound and those delineated into (b) H⋯H (42.4%), (c) C⋯H/ H⋯C (27.4%) and (d) N⋯H/H⋯N (9%) interactions, (e) significant hydrogen bonding and (f) extended supramolecular form.

6. Electronic transition analysis

Electro-conducting materials synthesized by conjugated organic compounds show promising electronic properties due to the availability of delocalized electrons, except for semiconducting materials such as TiO₂, ZnO and other metal oxide nano-materials, which are electro-conducting in themselves (Odziomek et al., 2017 ). The electronic properties of organic compounds depend on the electronic transition between the highest occupied molecular orbital (HOMO) or valence band and lowest occupied molecular orbital (LUMO) or conduction band. In a simple method, the energy band gap (Eg) of organic molecule is determined by a Tauc plot from the absorption spectra (λ_max = 245 nm, in this case). The band gap energy, Eg = 4.6 eV, of the title compound is very large (Fig. 5). This large band gap arises due to high π-conjugation or polarization in the title molecule system. The title molecule could be useful for developing or enhancing the organic electronic properties of conducting materials such as metal–organic frameworks.

Figure 5
Energy band gap of the title molecule by Tauc plot from absorption spectra.

7. Synthesis and crystallization

In an equimolar ratio, benzimidazole (2 g, 16.9 mmol) and dry K₂CO₃ (4.66 g, 33.85 mmol) were mixed in a round-bottom flask in acetonitrile (MeCN, 60 ml) under an inert atmosphere. The mixture was then allowed to stirred for 60 min at 363 K then treated with 2-(bromomethyl) benzonitrile (3.31 g, 16.9 mmol), and the resulting solution refluxed for 24 h. After completion of this step, the solution was allowed to cool to room temperature and the mixture was poured slowly onto ice–water (100 ml) under constant stirring. A greenish muddy crystalline precipitate was obtained and it was left to stand at 293 K for two days. After two days, a crystalline powder of 2-[(1H-benzo[d]imidazol-1-yl)methyl]benzonitrile was obtained (Ahmad et al., 2013).

The title compound was synthesized by hydrolysis of 2-[(1H-benzo[d]imidazol-1-yl)methyl]benzonitrile, 2 g being mixed with 20 equimolar of potassium hydroxide (6.86 g, 8.58 mmol) in water. The solution was refluxed at 373 K for 36 h, the resultant solution was then allowed to cool at room temperature and then poured onto ice–water, and after that acidified using 6 N HCl for protonation. The protonated solution was kept for slow evaporation. After two weeks, pale-yellow cubic crystals were obtained in good yield, which were suitable for data collection. The reaction scheme is shown in Fig. 6.

Figure 6
Reaction scheme.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O₂
M_r	252.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.5690 (8), 12.7956 (15), 14.1278 (16)
V (Å³)	1187.5 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.38 × 0.21 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
No. of measured, independent and observed [I ≥ 2u(I)] reflections	18798, 2095, 1759
R_int	0.107
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.091, 1.09
No. of reflections	2095
No. of parameters	176
No. of restraints	1
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28
Computer programs: APEX2 and SAINT (Bruker, 2014), olex2.solve (Bourhis et al., 2015 ), olex2.refine (Bourhis et al., 2015) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2091351

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989021006435/ex2044sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021006435/ex2044Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989021006435/ex2044Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-[(1H-Benzimidazol-1-yl)methyl]benzoic acid top

Crystal data top

C₁₅H₁₂N₂O₂	D_x = 1.411 Mg m⁻³
M_r = 252.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1209 reflections
a = 6.5690 (8) Å	θ = 2.9–22.1°
b = 12.7956 (15) Å	µ = 0.10 mm⁻¹
c = 14.1278 (16) Å	T = 100 K
V = 1187.5 (2) Å³	Block, colourless
Z = 4	0.38 × 0.21 × 0.14 mm
F(000) = 528.253

Data collection top

Bruker APEXII CCD diffractometer	1759 reflections with I ≥ 2u(I)
Detector resolution: X-ray pixels mm^-1	R_int = 0.107
φ and ω scans	θ_max = 25.1°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −8→8
	k = −17→17
18798 measured reflections	l = −18→18
2095 independent reflections

Refinement top

Refinement on F²	21 constraints
Least-squares matrix: full	Primary atom site location: iterative
R[F² > 2σ(F²)] = 0.044	All H-atom parameters refined
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0284P)² + 0.3178P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.004
2095 reflections	Δρ_max = 0.24 e Å⁻³
176 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint

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

	x	y	z	U_iso*/U_eq
C1	0.2861 (4)	0.82904 (18)	0.71973 (18)	0.0170 (6)
C2	0.4789 (4)	0.81263 (19)	0.66504 (18)	0.0166 (6)
C3	0.5267 (4)	0.88501 (19)	0.59451 (17)	0.0186 (6)
H3	0.4333 (4)	0.93965 (19)	0.58083 (17)	0.0223 (8)*
C4	0.7074 (4)	0.8790 (2)	0.54393 (18)	0.0213 (6)
H4	0.7359 (4)	0.9282 (2)	0.49537 (18)	0.0256 (8)*
C5	0.8447 (4)	0.80132 (19)	0.56462 (18)	0.0204 (7)
H5	0.9705 (4)	0.79769 (19)	0.53166 (18)	0.0245 (8)*
C6	0.7985 (4)	0.7280 (2)	0.63408 (18)	0.0196 (6)
H6	0.8941 (4)	0.6743 (2)	0.64778 (18)	0.0235 (7)*
C7	0.6164 (4)	0.7311 (2)	0.68391 (17)	0.0163 (6)
C8	0.5804 (4)	0.6465 (2)	0.75638 (17)	0.0179 (6)
H8a	0.7114 (4)	0.6115 (2)	0.77035 (17)	0.0215 (7)*
H8b	0.5313 (4)	0.6790 (2)	0.81572 (17)	0.0215 (7)*
C9	0.2503 (4)	0.54778 (19)	0.76721 (18)	0.0197 (6)
H9	0.2023 (4)	0.58470 (19)	0.82111 (18)	0.0236 (7)*
C10	0.2677 (4)	0.43913 (19)	0.65142 (17)	0.0176 (6)
C11	0.2311 (4)	0.3622 (2)	0.58413 (19)	0.0229 (6)
H11	0.1089 (4)	0.3224 (2)	0.58480 (19)	0.0274 (8)*
C12	0.3793 (4)	0.3456 (2)	0.51608 (19)	0.0248 (7)
H12	0.3580 (4)	0.2940 (2)	0.46874 (19)	0.0297 (8)*
C13	0.5601 (4)	0.40366 (19)	0.51595 (18)	0.0223 (7)
H13	0.6590 (4)	0.39013 (19)	0.46844 (18)	0.0267 (8)*
C14	0.5993 (4)	0.4801 (2)	0.58275 (18)	0.0197 (6)
H14	0.7226 (4)	0.5188 (2)	0.58240 (18)	0.0236 (8)*
C15	0.4494 (4)	0.49744 (19)	0.65048 (17)	0.0156 (6)
N1	0.4321 (3)	0.56758 (15)	0.72553 (14)	0.0158 (5)
N2	0.1467 (3)	0.47270 (16)	0.72598 (15)	0.0195 (5)
O1	0.1923 (3)	0.91615 (15)	0.69535 (13)	0.0228 (5)
O2	0.2246 (3)	0.77045 (13)	0.78116 (12)	0.0227 (4)
H1	0.078 (4)	0.924 (3)	0.727 (2)	0.077 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0165 (14)	0.0131 (13)	0.0214 (14)	−0.0029 (12)	−0.0021 (12)	−0.0043 (12)
C2	0.0186 (14)	0.0126 (13)	0.0184 (14)	−0.0064 (11)	−0.0017 (12)	−0.0040 (11)
C3	0.0246 (16)	0.0118 (14)	0.0193 (14)	0.0002 (12)	−0.0039 (12)	−0.0027 (11)
C4	0.0257 (16)	0.0207 (14)	0.0175 (14)	−0.0068 (13)	0.0054 (13)	−0.0014 (12)
C5	0.0217 (15)	0.0172 (14)	0.0223 (16)	−0.0060 (12)	0.0068 (12)	−0.0042 (12)
C6	0.0187 (14)	0.0166 (13)	0.0235 (15)	0.0024 (12)	−0.0007 (12)	−0.0050 (12)
C7	0.0166 (13)	0.0158 (14)	0.0164 (13)	−0.0037 (12)	−0.0020 (11)	−0.0056 (11)
C8	0.0166 (13)	0.0181 (14)	0.0190 (14)	−0.0010 (12)	−0.0033 (12)	−0.0009 (12)
C9	0.0241 (15)	0.0163 (14)	0.0186 (14)	0.0038 (12)	0.0022 (13)	0.0027 (12)
C10	0.0210 (14)	0.0149 (13)	0.0170 (13)	0.0010 (12)	−0.0025 (12)	0.0032 (11)
C11	0.0235 (15)	0.0183 (14)	0.0268 (15)	−0.0006 (13)	−0.0034 (13)	0.0007 (12)
C12	0.0339 (17)	0.0159 (14)	0.0244 (16)	0.0026 (14)	−0.0028 (14)	−0.0030 (13)
C13	0.0295 (17)	0.0185 (15)	0.0188 (14)	0.0077 (12)	0.0031 (13)	0.0007 (12)
C14	0.0201 (15)	0.0178 (14)	0.0212 (14)	−0.0002 (12)	0.0010 (12)	0.0031 (12)
C15	0.0198 (15)	0.0117 (13)	0.0153 (13)	0.0008 (11)	−0.0027 (12)	0.0017 (11)
N1	0.0160 (12)	0.0144 (11)	0.0170 (11)	−0.0010 (9)	−0.0006 (10)	0.0000 (10)
N2	0.0222 (12)	0.0136 (12)	0.0226 (12)	−0.0009 (10)	0.0014 (11)	0.0032 (10)
O1	0.0170 (11)	0.0199 (10)	0.0316 (11)	0.0030 (9)	0.0012 (9)	0.0042 (9)
O2	0.0250 (10)	0.0171 (9)	0.0259 (11)	0.0012 (8)	0.0075 (9)	0.0031 (9)

Geometric parameters (Å, º) top

C1—C2	1.499 (3)	C9—H9	0.950 (4)
C1—O1	1.319 (3)	C9—N1	1.356 (3)
C1—O2	1.216 (3)	C9—N2	1.313 (3)
C2—C3	1.396 (3)	C10—C11	1.390 (3)
C2—C7	1.405 (3)	C10—C15	1.408 (3)
C3—H3	0.950 (4)	C10—N2	1.388 (3)
C3—C4	1.388 (3)	C11—H11	0.9501 (4)
C4—H4	0.950 (4)	C11—C12	1.385 (4)
C4—C5	1.373 (4)	C12—H12	0.950 (4)
C5—H5	0.950 (4)	C12—C13	1.401 (4)
C5—C6	1.391 (4)	C13—H13	0.950 (4)
C6—H6	0.951 (4)	C13—C14	1.383 (3)
C6—C7	1.389 (4)	C14—H14	0.949 (4)
C7—C8	1.508 (3)	C14—C15	1.391 (4)
C8—H8a	0.990 (4)	C15—N1	1.394 (3)
C8—H8b	0.990 (3)	O1—H1	0.878 (18)
C8—N1	1.469 (3)

O1—C1—C2	112.3 (2)	N1—C9—H9	123.20 (14)
O2—C1—C2	124.2 (2)	N2—C9—H9	123.20 (15)
O2—C1—O1	123.5 (2)	N2—C9—N1	113.6 (2)
C3—C2—C1	117.7 (2)	C15—C10—C11	121.1 (2)
C7—C2—C1	123.3 (2)	N2—C10—C11	129.7 (2)
C7—C2—C3	118.9 (2)	N2—C10—C15	109.2 (2)
H3—C3—C2	119.23 (15)	H11—C11—C10	121.25 (15)
C4—C3—C2	121.5 (2)	C12—C11—C10	117.5 (3)
C4—C3—H3	119.23 (15)	C12—C11—H11	121.25 (16)
H4—C4—C3	120.26 (15)	H12—C12—C11	119.48 (16)
C5—C4—C3	119.5 (2)	C13—C12—C11	121.0 (2)
C5—C4—H4	120.26 (15)	C13—C12—H12	119.48 (15)
H5—C5—C4	120.16 (15)	H13—C13—C12	118.94 (15)
C6—C5—C4	119.7 (2)	C14—C13—C12	122.1 (2)
C6—C5—H5	120.16 (16)	C14—C13—H13	118.94 (16)
H6—C6—C5	119.13 (16)	H14—C14—C13	121.59 (16)
C7—C6—C5	121.7 (2)	C15—C14—C13	116.8 (3)
C7—C6—H6	119.13 (16)	C15—C14—H14	121.59 (16)
C6—C7—C2	118.6 (2)	C14—C15—C10	121.5 (2)
C8—C7—C2	124.1 (2)	N1—C15—C10	105.3 (2)
C8—C7—C6	117.3 (2)	N1—C15—C14	133.2 (2)
H8a—C8—C7	108.91 (14)	C9—N1—C8	125.7 (2)
H8b—C8—C7	108.91 (13)	C15—N1—C8	127.9 (2)
H8b—C8—H8a	107.7 (3)	C15—N1—C9	106.4 (2)
N1—C8—C7	113.31 (19)	C10—N2—C9	105.4 (2)
N1—C8—H8a	108.91 (12)	H1—O1—C1	111 (2)
N1—C8—H8b	108.91 (12)

C1—C2—C3—C4	176.5 (2)	C8—N1—C9—N2	−179.6 (2)
C1—C2—C7—C6	−174.8 (2)	C8—N1—C15—C10	179.7 (3)
C1—C2—C7—C8	4.3 (3)	C8—N1—C15—C14	−1.3 (3)
C2—C3—C4—C5	−1.2 (3)	C9—N1—C15—C10	1.0 (2)
C2—C7—C6—C5	−1.9 (3)	C9—N1—C15—C14	179.9 (2)
C2—C7—C8—N1	75.2 (3)	C9—N2—C10—C11	−179.2 (2)
C3—C4—C5—C6	1.8 (3)	C9—N2—C10—C15	0.4 (2)
C4—C5—C6—C7	−0.2 (3)	C10—C11—C12—C13	0.6 (3)
C5—C6—C7—C8	178.9 (2)	C10—C15—C14—C13	0.7 (3)
C6—C7—C8—N1	−105.6 (2)	C11—C12—C13—C14	−0.3 (3)
C7—C8—N1—C9	−116.8 (2)	C12—C13—C14—C15	−0.4 (3)
C7—C8—N1—C15	64.7 (3)	C13—C14—C15—N1	−178.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/N2/C9/C10/C15, C2–C7, C10–C15 and N1/N2/C9–15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.88 (3)	1.73 (3)	2.592 (3)	164 (4)
C8—H8A···O1ⁱⁱ	0.99 (1)	2.62 (1)	3.374 (3)	133 (1)
C3—H3···O1	0.95 (1)	2.28 (1)	2.648 (3)	102 (1)
C8—H8B···O2	0.99 (1)	2.38 (1)	2.846 (3)	108 (1)
C9—H9···O2	0.95 (1)	2.45 (1)	2.861 (3)	106 (1)
C4—H4···Cg1ⁱⁱⁱ	0.95 (1)	2.99 (1)	3.865 (3)	155 (1)
C4—H4···Cg3ⁱⁱⁱ	0.95 (1)	2.51 (1)	3.408 (3)	157 (1)
C4—H4···Cg4ⁱⁱⁱ	0.95 (1)	2.51 (1)	3.454 (3)	170 (1)
C5—H5···Cg2ⁱⁱⁱ	0.95 (1)	2.76 (1)	3.554 (3)	142 (1)

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x+1/2, −y+3/2, −z+1.

Acknowledgements

The authors are grateful to the Department of Applied Chemistry, Aligarh Muslim University, for providing laboratory facilities. Author contribution are as follows. Conceptualization, MA and AM; methodology, AA and MS; investigation, MM, SK, SJ and JAK; writing (original draft), AA and ND; writing (review and editing of the manuscript), AAfall and ADA; visualization, MA, AA and AM; funding acquisition, AM; resources, ND and MA; supervision, MA and AM.

Funding information

MA acknowledges the start-up grant received from UGC, India. AA, MM and SK also thank the UGC for the Non-NET scheme. AM acknowledges support from the Department of Pharmacy, University of Science and Technology, Ibb Branch, Yemen.

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Volume 77| Part 7| July 2021| Pages 755-758

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure, Hirshfeld and electronic transition analysis of 2-[(1H-benzimidazol-1-yl)meth­yl]benzoic acid

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Hirshfeld surface analysis

6. Electronic transition analysis

7. Synthesis and crystallization

8. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Crystal structure, Hirshfeld and electronic transition analysis of 2-[(1H-benzimidazol-1-yl)methyl]benzoic acid

3. Supramolecular features