2-(2-Hy­droxy-3-meth­oxy­phen­yl)-1H-benzimidazol-3-ium perchlorate

Chen, C.; Li, H.-X.; Hou, G.-F.; Li, G.-M.

doi:10.1107/S1600536812023422

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1920

doi:10.1107/S1600536812023422

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2-(2-Hydroxy-3-methoxyphenyl)-1H-benzimidazol-3-ium perchlorate

Chuan Chen,^a Hong-Xing Li,^a Guang-Feng Hou ^a and Guang-Ming Li ^a ^*

^aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gmli_2000@163.com

(Received 12 May 2012; accepted 22 May 2012; online 31 May 2012)

In the title molecular salt, C₁₄H₁₃N₂O₂⁺·ClO₄⁻, the ring systems in the cation are almost coplanar [dihedral angle = 5.53 (13)°]. Intramolecular N—H⋯O and O—H⋯O hydrogen bonds generate S(6) and S(5) rings, respectively. In the crystal, the two H atoms involved in the intramolecular hydrogen bonds also participate in intermolecular links to acceptor O atoms of the perchlorate anions. A simple intermolecular N—H⋯O bond also occurs. Together, these form a double-chain structure along [101].

Related literature

For a related structure, see: Yang et al. (2010 ).

Experimental

Crystal data

C₁₄H₁₃N₂O₂⁺·ClO₄⁻
M_r = 340.71
Monoclinic, P 2₁ /c
a = 7.7698 (16) Å
b = 20.462 (4) Å
c = 9.856 (2) Å
β = 113.09 (3)°
V = 1441.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.50 × 0.45 × 0.42 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.864, T_max = 0.884
13683 measured reflections
3285 independent reflections
2025 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.140
S = 1.03
3285 reflections
218 parameters
15 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82 (1)	2.20 (3)	2.635 (3)	114 (3)
O1—H1⋯O4ⁱ	0.82 (1)	2.13 (2)	2.869 (3)	151 (3)
N1—H101⋯O1	0.90 (1)	2.12 (3)	2.660 (3)	118 (3)
N1—H101⋯O5	0.90 (1)	2.04 (2)	2.819 (3)	144 (3)
N2—H102⋯O3ⁱⁱ	0.89 (1)	2.06 (2)	2.857 (4)	149 (3)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x-1, y, z-1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812023422/hb6796sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023422/hb6796Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023422/hb6796Isup3.cml

checkCIF report

Comment top

The title compound is an unexpected product during the process of preparing the N,N'-phenyl-bis(3-methoxysalicylaldimine) and Ce complex. We speculate that the title ligand was produced form the decomposition of N,N'-phenyl-bis(3-methoxysalicylaldimine). A similar ligand and Yb cation constructed metallic cluster has been reproted by Yang's group (Yang et al. 2010).

In the title compound, [C₁₄H₁₃N₂O₂][ClO₄], the phenyl ring and benzimidazol ring are almost conplane with small dihedral angle of 5.517 (1) ° (Figure 1). Intermolecular N—H···O and O—H···0 hydrogen bonds link these protonated ligands and perchlorate anions to form double chain structure along [101] (Figure 2, Table 1).

Related literature top

For a related structure, see: Yang et al. (2010).

Experimental top

A solution of N,N'-phenyl-bis(3-methoxysalicylaldimine) (0.1502 g, 0.4 mmol) in 10 mL CH₂Cl₂, was added dropwise to a solution of [Ce(ClO₄)₃]˙9H₂O (0.1984 g, 0.4 mmol) in 10 mL of CH₃OH solution, after then the mixsure was keeping stir about 12h. Pale brown blocks were obtained after seven days. Elemental Anal. Calc. for C₁₄H₁₃ClN₂O₆: C, 49.35; H, 3.85; Cl, 10.41; N, 8.22; O, 28.17 wt%, Found: C, 49.32; H, 3.86; Cl, 10.40; N, 8.24 O, 28.15 wt%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The double chain structure.

2-(2-Hydroxy-3-methoxyphenyl)-1H-benzimidazol-3-ium perchlorate top

Crystal data top

C₁₄H₁₃N₂O₂⁺·ClO₄⁻	F(000) = 704
M_r = 340.71	D_x = 1.570 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7910 reflections
a = 7.7698 (16) Å	θ = 3.0–27.4°
b = 20.462 (4) Å	µ = 0.30 mm⁻¹
c = 9.856 (2) Å	T = 293 K
β = 113.09 (3)°	Block, colorless
V = 1441.4 (5) Å³	0.50 × 0.45 × 0.42 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3285 independent reflections
Radiation source: fine-focus sealed tube	2025 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scan	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→9
T_min = 0.864, T_max = 0.884	k = −26→26
13683 measured reflections	l = −12→12

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0569P)² + 0.5284P] where P = (F_o² + 2F_c²)/3
3285 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.37 e Å⁻³
15 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₄H₁₃N₂O₂⁺·ClO₄⁻	V = 1441.4 (5) Å³
M_r = 340.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7698 (16) Å	µ = 0.30 mm⁻¹
b = 20.462 (4) Å	T = 293 K
c = 9.856 (2) Å	0.50 × 0.45 × 0.42 mm
β = 113.09 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3285 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2025 reflections with I > 2σ(I)
T_min = 0.864, T_max = 0.884	R_int = 0.061
13683 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	15 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
3285 reflections	Δρ_min = −0.32 e Å⁻³
218 parameters

Special details top

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. isor 0.01 o5 o6 dfix 0.90 0.01 h101 n1 h102 n2 dfix 0.82 0.01 o1 h1 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.

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

	x	y	z	U_iso*/U_eq
O1	0.2919 (3)	0.54938 (10)	0.6641 (2)	0.0448 (5)
H1	0.318 (5)	0.5726 (15)	0.737 (3)	0.067*
O2	0.1478 (3)	0.66205 (11)	0.6962 (2)	0.0536 (6)
O3	0.8344 (4)	0.46040 (16)	0.9925 (3)	0.0933 (10)
O4	0.5840 (4)	0.41460 (17)	1.0309 (3)	0.0886 (9)
O5	0.5714 (4)	0.43412 (17)	0.7935 (2)	0.0900 (10)
O6	0.7608 (6)	0.35259 (16)	0.9385 (4)	0.1203 (13)
C1	0.3647 (4)	0.39510 (13)	0.4381 (3)	0.0348 (6)
C2	0.4842 (4)	0.34335 (15)	0.5008 (3)	0.0451 (7)
H2	0.5525	0.3404	0.6020	0.054*
C3	0.4962 (4)	0.29644 (16)	0.4046 (4)	0.0528 (8)
H3	0.5726	0.2603	0.4424	0.063*
C4	0.3972 (4)	0.30136 (17)	0.2519 (4)	0.0556 (8)
H4	0.4126	0.2692	0.1910	0.067*
C5	0.2779 (5)	0.35259 (17)	0.1898 (3)	0.0540 (8)
H5	0.2119	0.3559	0.0884	0.065*
C6	0.2609 (4)	0.39922 (14)	0.2863 (3)	0.0401 (6)
C7	0.1917 (4)	0.48632 (14)	0.3912 (3)	0.0357 (6)
C8	0.1067 (4)	0.54718 (13)	0.4073 (3)	0.0361 (6)
C9	−0.0326 (4)	0.57649 (15)	0.2837 (3)	0.0458 (7)
H9	−0.0722	0.5561	0.1921	0.055*
C10	−0.1100 (4)	0.63489 (16)	0.2979 (3)	0.0513 (8)
H10	−0.2025	0.6537	0.2156	0.062*
C11	−0.0525 (4)	0.66657 (16)	0.4331 (3)	0.0481 (7)
H11	−0.1035	0.7068	0.4407	0.058*
C12	0.0804 (4)	0.63794 (14)	0.5558 (3)	0.0412 (7)
C13	0.1614 (4)	0.57819 (14)	0.5442 (3)	0.0371 (6)
C14	0.0861 (5)	0.72523 (17)	0.7194 (4)	0.0610 (9)
H14A	0.1256	0.7573	0.6665	0.091*
H14B	0.1392	0.7353	0.8228	0.091*
H14C	−0.0479	0.7255	0.6845	0.091*
Cl1	0.68517 (11)	0.41471 (4)	0.93839 (7)	0.0463 (2)
N1	0.3185 (3)	0.45039 (11)	0.4985 (2)	0.0351 (5)
H101	0.367 (4)	0.4594 (16)	0.5954 (13)	0.053*
N2	0.1566 (4)	0.45555 (13)	0.2634 (2)	0.0442 (6)
H102	0.079 (4)	0.4709 (17)	0.177 (2)	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0481 (12)	0.0439 (12)	0.0338 (9)	0.0034 (10)	0.0068 (9)	−0.0052 (8)
O2	0.0597 (14)	0.0452 (13)	0.0546 (12)	0.0044 (11)	0.0210 (11)	−0.0124 (10)
O3	0.0832 (19)	0.114 (3)	0.0514 (14)	−0.0493 (18)	−0.0079 (13)	0.0054 (15)
O4	0.0807 (19)	0.135 (3)	0.0592 (15)	0.0109 (19)	0.0376 (15)	0.0040 (16)
O5	0.0704 (18)	0.139 (3)	0.0349 (12)	−0.0005 (18)	−0.0075 (11)	0.0044 (14)
O6	0.186 (4)	0.062 (2)	0.146 (3)	0.038 (2)	0.100 (3)	0.0105 (19)
C1	0.0364 (14)	0.0327 (15)	0.0362 (12)	−0.0054 (11)	0.0151 (12)	−0.0020 (11)
C2	0.0398 (16)	0.0443 (18)	0.0456 (15)	0.0021 (13)	0.0107 (13)	−0.0011 (13)
C3	0.0423 (17)	0.0423 (19)	0.072 (2)	0.0015 (14)	0.0206 (16)	−0.0054 (15)
C4	0.0515 (19)	0.055 (2)	0.0638 (19)	−0.0042 (16)	0.0265 (17)	−0.0215 (16)
C5	0.058 (2)	0.059 (2)	0.0426 (15)	−0.0010 (17)	0.0173 (15)	−0.0135 (14)
C6	0.0444 (16)	0.0398 (17)	0.0359 (13)	−0.0059 (12)	0.0155 (12)	−0.0038 (11)
C7	0.0386 (15)	0.0365 (15)	0.0295 (12)	−0.0064 (12)	0.0106 (11)	0.0014 (10)
C8	0.0355 (14)	0.0323 (15)	0.0386 (13)	−0.0028 (12)	0.0123 (11)	0.0020 (11)
C9	0.0497 (17)	0.0418 (18)	0.0381 (14)	−0.0027 (14)	0.0089 (13)	0.0052 (12)
C10	0.0509 (19)	0.0452 (19)	0.0512 (17)	0.0056 (15)	0.0129 (15)	0.0152 (14)
C11	0.0478 (18)	0.0363 (17)	0.0629 (18)	0.0025 (14)	0.0245 (16)	0.0070 (14)
C12	0.0423 (16)	0.0353 (16)	0.0492 (15)	−0.0056 (12)	0.0214 (14)	−0.0032 (12)
C13	0.0330 (14)	0.0363 (16)	0.0382 (13)	−0.0067 (12)	0.0100 (11)	0.0022 (11)
C14	0.069 (2)	0.044 (2)	0.075 (2)	−0.0003 (17)	0.0338 (19)	−0.0128 (17)
Cl1	0.0494 (4)	0.0493 (4)	0.0333 (3)	−0.0014 (4)	0.0086 (3)	−0.0021 (3)
N1	0.0388 (12)	0.0355 (13)	0.0277 (10)	−0.0017 (10)	0.0094 (10)	−0.0003 (9)
N2	0.0529 (15)	0.0443 (15)	0.0278 (10)	0.0031 (12)	0.0075 (11)	0.0012 (9)

Geometric parameters (Å, º) top

O1—C13	1.353 (3)	C6—N2	1.376 (4)
O1—H1	0.816 (10)	C7—N2	1.337 (3)
O2—C12	1.365 (3)	C7—N1	1.346 (3)
O2—C14	1.428 (4)	C7—C8	1.447 (4)
O3—Cl1	1.420 (3)	C8—C13	1.398 (4)
O4—Cl1	1.419 (3)	C8—C9	1.408 (4)
O5—Cl1	1.410 (2)	C9—C10	1.369 (4)
O6—Cl1	1.400 (3)	C9—H9	0.9300
C1—C2	1.384 (4)	C10—C11	1.389 (4)
C1—N1	1.389 (3)	C10—H10	0.9300
C1—C6	1.396 (4)	C11—C12	1.375 (4)
C2—C3	1.378 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.400 (4)
C3—C4	1.400 (4)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.374 (5)	C14—H14C	0.9600
C4—H4	0.9300	N1—H101	0.897 (10)
C5—C6	1.389 (4)	N2—H102	0.885 (10)
C5—H5	0.9300

C13—O1—H1	111 (3)	C9—C10—H10	119.5
C12—O2—C14	118.0 (3)	C11—C10—H10	119.5
C2—C1—N1	132.2 (3)	C12—C11—C10	119.5 (3)
C2—C1—C6	122.0 (3)	C12—C11—H11	120.2
N1—C1—C6	105.8 (2)	C10—C11—H11	120.2
C3—C2—C1	116.1 (3)	O2—C12—C11	126.5 (3)
C3—C2—H2	121.9	O2—C12—C13	113.1 (3)
C1—C2—H2	121.9	C11—C12—C13	120.5 (3)
C2—C3—C4	122.2 (3)	O1—C13—C8	119.0 (3)
C2—C3—H3	118.9	O1—C13—C12	121.1 (2)
C4—C3—H3	118.9	C8—C13—C12	119.9 (3)
C5—C4—C3	121.6 (3)	O2—C14—H14A	109.5
C5—C4—H4	119.2	O2—C14—H14B	109.5
C3—C4—H4	119.2	H14A—C14—H14B	109.5
C4—C5—C6	116.6 (3)	O2—C14—H14C	109.5
C4—C5—H5	121.7	H14A—C14—H14C	109.5
C6—C5—H5	121.7	H14B—C14—H14C	109.5
N2—C6—C5	132.1 (3)	O6—Cl1—O5	110.6 (2)
N2—C6—C1	106.4 (2)	O6—Cl1—O4	109.7 (2)
C5—C6—C1	121.5 (3)	O5—Cl1—O4	111.48 (18)
N2—C7—N1	107.4 (2)	O6—Cl1—O3	108.5 (2)
N2—C7—C8	125.1 (2)	O5—Cl1—O3	106.87 (18)
N1—C7—C8	127.5 (2)	O4—Cl1—O3	109.64 (19)
C13—C8—C9	118.8 (3)	C7—N1—C1	109.9 (2)
C13—C8—C7	121.2 (2)	C7—N1—H101	127 (2)
C9—C8—C7	120.0 (2)	C1—N1—H101	123 (2)
C10—C9—C8	120.2 (3)	C7—N2—C6	110.5 (2)
C10—C9—H9	119.9	C7—N2—H102	123 (2)
C8—C9—H9	119.9	C6—N2—H102	126 (2)
C9—C10—C11	121.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82 (1)	2.20 (3)	2.635 (3)	114 (3)
O1—H1···O4ⁱ	0.82 (1)	2.13 (2)	2.869 (3)	151 (3)
N1—H101···O1	0.90 (1)	2.12 (3)	2.660 (3)	118 (3)
N1—H101···O5	0.90 (1)	2.04 (2)	2.819 (3)	144 (3)
N2—H102···O3ⁱⁱ	0.89 (1)	2.06 (2)	2.857 (4)	149 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₂O₂⁺·ClO₄⁻
M_r	340.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.7698 (16), 20.462 (4), 9.856 (2)
β (°)	113.09 (3)
V (Å³)	1441.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.50 × 0.45 × 0.42

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.864, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	13683, 3285, 2025
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.140, 1.03
No. of reflections	3285
No. of parameters	218
No. of restraints	15
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.32

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.816 (10)	2.20 (3)	2.635 (3)	114 (3)
O1—H1···O4ⁱ	0.816 (10)	2.13 (2)	2.869 (3)	151 (3)
N1—H101···O1	0.897 (10)	2.12 (3)	2.660 (3)	118 (3)
N1—H101···O5	0.897 (10)	2.04 (2)	2.819 (3)	144 (3)
N2—H102···O3ⁱⁱ	0.885 (10)	2.06 (2)	2.857 (4)	149 (3)

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

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (Nos. 20872030 and 20972043), Heilongjiang Province (Nos. 2009RFXXG201, GC09A402 and 2010td03) and Heilongjiang University.

References

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