2-(1H-Benzimidazol-2-yl)-4-nitro­phenol

Sun, J.; Tong, X.

doi:10.1107/S1600536811001644

organic compounds

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Volume 67| Part 2| February 2011| Page o409

doi:10.1107/S1600536811001644

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2-(1H-Benzimidazol-2-yl)-4-nitrophenol

Jingya Sun ^a ^* and Xiangdi Tong ^a

^aCollege of Marine Sciences, Zhejiang Ocean University, Zhoushan 316000, People's Republic of China
^*Correspondence e-mail: jingya_sun@163.com

(Received 10 January 2011; accepted 11 January 2011; online 15 January 2011)

The title compound, C₁₃H₉N₃O₃, was prepared by the reaction of 5-nitrosalicylaldehyde with 1,2-diaminobenzene in methanol. The whole molecule is approximately planar, with a mean deviation from the plane defined by the non-H atoms of 0.0311 (4) Å, and with a dihedral angle between the benzene ring and the benzimidazole ring system of 1.1 (3)°. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal, adjacent molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For Schiff base compounds, see: Miura et al. (2009 ); Zhao et al. (2010 ); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₉N₃O₃
M_r = 255.23
Monoclinic, P 2₁ /c
a = 8.117 (3) Å
b = 6.769 (2) Å
c = 20.842 (3) Å
β = 99.235 (2)°
V = 1130.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.978, T_max = 0.980
8933 measured reflections
2469 independent reflections
1283 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.153
S = 1.04
2469 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.90 (1)	2.02 (1)	2.898 (3)	164 (3)
O1—H1⋯N1	0.82	1.85	2.590 (3)	149
Symmetry code: (i) -x+1, -y, -z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001644/hg2791sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001644/hg2791Isup2.hkl

checkCIF report

Comment top

The condensation reaction between aldehydes with organic primary amines readily forms Schiff bases containing the typical –C=N– groups (Miura et al., 2009; Zhao et al., 2010; Karadağ et al., 2011; Bingöl Alpaslan et al., 2010). In this paper, the title compound (Fig. 1) was prepared by the reaction of 5-nitrosalicylaldehyde with 1,2-diaminobenzene in methanol.

The whole molecule of the compound is approximately planar, with mean deviation from the plane defined by the non-hydrogen atoms of 0.0311 (4) Å, and with the dihedral angle between the benzene ring and the Benzimidazole ring of 1.1 (3)°. All the bond lengths are within normal ranges (Allen et al., 1987). There is an intramolecular O—H···N hydrogen bond in the molecule (Table 1). In the crystal structure, adjacent two molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form a dimer (Fig. 2).

Related literature top

For Schiff base compounds, see: Miura et al. (2009); Zhao et al. (2010); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010). For bond-length data, see: Allen et al. (1987).

Experimental top

5-Nitrosalicylaldehyde (1.0 mmol, 0.167 g) and 1,2-diaminobenzene (0.5 mmol, 0.054 g) were refluxed for 30 min in 30 ml me thanol, and cooled to room temperature to give colorless solid, which was isolated by filtration. Single crystals of the title compound were formed by recrystallization of the solid in methanol.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compounds with atom labels and the 30% probability displacement ellipsoids. Intramolecular O—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. The molecular packing of the title compound. Hydrogen bonds are shown as dashed lines.

2-(1H-Benzimidazol-2-yl)-4-nitrophenol top

Crystal data top

C₁₃H₉N₃O₃	F(000) = 528
M_r = 255.23	D_x = 1.500 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1124 reflections
a = 8.117 (3) Å	θ = 2.5–24.5°
b = 6.769 (2) Å	µ = 0.11 mm⁻¹
c = 20.842 (3) Å	T = 298 K
β = 99.235 (2)°	Block, yellow
V = 1130.2 (5) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2469 independent reflections
Radiation source: fine-focus sealed tube	1283 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.978, T_max = 0.980	k = −8→8
8933 measured reflections	l = −26→24

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0589P)² + 0.1494P] where P = (F_o² + 2F_c²)/3
2469 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₃H₉N₃O₃	V = 1130.2 (5) Å³
M_r = 255.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.117 (3) Å	µ = 0.11 mm⁻¹
b = 6.769 (2) Å	T = 298 K
c = 20.842 (3) Å	0.20 × 0.20 × 0.18 mm
β = 99.235 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2469 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1283 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.980	R_int = 0.061
8933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	1 restraint
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
2469 reflections	Δρ_min = −0.14 e Å⁻³
176 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
O1	0.7974 (3)	0.7492 (3)	0.12518 (10)	0.0680 (7)
H1	0.8172	0.7776	0.0889	0.102*
O2	0.4484 (3)	−0.0641 (3)	0.07368 (10)	0.0687 (7)
O3	0.4555 (3)	−0.0423 (3)	0.17662 (11)	0.0764 (8)
N1	0.8286 (3)	0.7006 (4)	0.00445 (12)	0.0547 (7)
N2	0.7411 (3)	0.4267 (3)	−0.04913 (12)	0.0495 (7)
N3	0.4870 (3)	0.0226 (4)	0.12571 (12)	0.0520 (7)
C1	0.6985 (3)	0.4551 (4)	0.06634 (13)	0.0425 (7)
C2	0.7228 (4)	0.5722 (4)	0.12303 (15)	0.0477 (8)
C3	0.6712 (4)	0.5046 (5)	0.17926 (14)	0.0562 (9)
H3	0.6878	0.5828	0.2164	0.067*
C4	0.5966 (4)	0.3252 (4)	0.18085 (14)	0.0492 (8)
H4	0.5632	0.2799	0.2189	0.059*
C5	0.5710 (3)	0.2113 (4)	0.12517 (14)	0.0425 (7)
C6	0.6205 (3)	0.2741 (4)	0.06832 (13)	0.0423 (7)
H6	0.6016	0.1950	0.0314	0.051*
C7	0.7560 (3)	0.5267 (4)	0.00778 (14)	0.0461 (7)
C8	0.8628 (4)	0.7151 (4)	−0.05876 (14)	0.0484 (8)
C9	0.8092 (3)	0.5440 (4)	−0.09285 (15)	0.0475 (7)
C10	0.8259 (4)	0.5165 (5)	−0.15689 (15)	0.0594 (9)
H10	0.7902	0.4011	−0.1791	0.071*
C11	0.8983 (4)	0.6692 (5)	−0.18671 (16)	0.0645 (10)
H11	0.9114	0.6565	−0.2300	0.077*
C12	0.9518 (4)	0.8413 (5)	−0.15324 (18)	0.0694 (10)
H12	0.9996	0.9414	−0.1747	0.083*
C13	0.9354 (4)	0.8666 (5)	−0.08904 (17)	0.0645 (9)
H13	0.9719	0.9816	−0.0668	0.077*
H2	0.698 (4)	0.307 (2)	−0.0610 (15)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0862 (18)	0.0561 (14)	0.0638 (17)	−0.0234 (12)	0.0183 (14)	−0.0113 (11)
O2	0.1090 (19)	0.0552 (13)	0.0445 (14)	−0.0268 (12)	0.0203 (13)	−0.0100 (11)
O3	0.122 (2)	0.0662 (15)	0.0487 (14)	−0.0165 (14)	0.0369 (14)	0.0101 (12)
N1	0.0620 (18)	0.0552 (15)	0.0460 (17)	−0.0161 (13)	0.0055 (13)	0.0067 (13)
N2	0.0588 (17)	0.0435 (14)	0.0465 (16)	−0.0102 (12)	0.0096 (13)	0.0012 (13)
N3	0.0713 (18)	0.0478 (15)	0.0403 (16)	−0.0029 (13)	0.0192 (13)	0.0019 (13)
C1	0.0475 (18)	0.0399 (16)	0.0387 (17)	−0.0038 (14)	0.0033 (14)	0.0005 (13)
C2	0.0458 (18)	0.0434 (17)	0.052 (2)	−0.0057 (14)	0.0037 (15)	−0.0061 (15)
C3	0.070 (2)	0.058 (2)	0.0413 (19)	−0.0124 (17)	0.0117 (16)	−0.0126 (16)
C4	0.061 (2)	0.0553 (19)	0.0328 (17)	−0.0008 (16)	0.0108 (15)	−0.0021 (15)
C5	0.0489 (18)	0.0390 (15)	0.0393 (18)	−0.0027 (14)	0.0058 (14)	0.0026 (13)
C6	0.0547 (18)	0.0418 (16)	0.0302 (16)	−0.0045 (14)	0.0061 (13)	−0.0025 (13)
C7	0.0497 (18)	0.0412 (16)	0.0462 (19)	−0.0073 (14)	0.0038 (14)	0.0028 (15)
C8	0.0494 (19)	0.0516 (18)	0.0422 (19)	−0.0055 (15)	0.0014 (15)	0.0085 (15)
C9	0.0442 (18)	0.0535 (18)	0.0447 (19)	−0.0026 (15)	0.0070 (14)	0.0107 (15)
C10	0.063 (2)	0.065 (2)	0.050 (2)	0.0030 (17)	0.0071 (16)	0.0009 (17)
C11	0.069 (2)	0.082 (3)	0.045 (2)	0.003 (2)	0.0157 (18)	0.0130 (19)
C12	0.070 (2)	0.075 (2)	0.064 (3)	−0.009 (2)	0.0121 (19)	0.028 (2)
C13	0.070 (2)	0.061 (2)	0.062 (2)	−0.0165 (18)	0.0115 (18)	0.0127 (18)

Geometric parameters (Å, º) top

O1—C2	1.340 (3)	C3—H3	0.9300
O1—H1	0.8200	C4—C5	1.381 (4)
O2—N3	1.228 (3)	C4—H4	0.9300
O3—N3	1.213 (3)	C5—C6	1.378 (4)
N1—C7	1.323 (3)	C6—H6	0.9300
N1—C8	1.393 (4)	C8—C13	1.384 (4)
N2—C7	1.354 (3)	C8—C9	1.392 (4)
N2—C9	1.388 (3)	C9—C10	1.376 (4)
N2—H2	0.902 (10)	C10—C11	1.385 (4)
N3—C5	1.449 (3)	C10—H10	0.9300
C1—C6	1.383 (4)	C11—C12	1.391 (5)
C1—C2	1.410 (4)	C11—H11	0.9300
C1—C7	1.458 (4)	C12—C13	1.376 (5)
C2—C3	1.384 (4)	C12—H12	0.9300
C3—C4	1.360 (4)	C13—H13	0.9300

C2—O1—H1	109.5	C5—C6—H6	120.1
C7—N1—C8	105.7 (2)	C1—C6—H6	120.1
C7—N2—C9	107.5 (2)	N1—C7—N2	112.1 (2)
C7—N2—H2	132 (2)	N1—C7—C1	123.0 (3)
C9—N2—H2	121 (2)	N2—C7—C1	124.9 (2)
O3—N3—O2	122.7 (3)	C13—C8—C9	120.3 (3)
O3—N3—C5	119.4 (3)	C13—C8—N1	130.4 (3)
O2—N3—C5	117.9 (2)	C9—C8—N1	109.3 (2)
C6—C1—C2	118.4 (3)	C10—C9—N2	132.1 (3)
C6—C1—C7	121.9 (2)	C10—C9—C8	122.5 (3)
C2—C1—C7	119.6 (2)	N2—C9—C8	105.4 (3)
O1—C2—C3	117.6 (3)	C9—C10—C11	116.7 (3)
O1—C2—C1	122.2 (3)	C9—C10—H10	121.7
C3—C2—C1	120.2 (3)	C11—C10—H10	121.7
C4—C3—C2	120.8 (3)	C10—C11—C12	121.4 (3)
C4—C3—H3	119.6	C10—C11—H11	119.3
C2—C3—H3	119.6	C12—C11—H11	119.3
C3—C4—C5	119.1 (3)	C13—C12—C11	121.4 (3)
C3—C4—H4	120.5	C13—C12—H12	119.3
C5—C4—H4	120.5	C11—C12—H12	119.3
C6—C5—C4	121.7 (3)	C12—C13—C8	117.7 (3)
C6—C5—N3	118.8 (2)	C12—C13—H13	121.1
C4—C5—N3	119.6 (3)	C8—C13—H13	121.1
C5—C6—C1	119.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	2.02 (1)	2.898 (3)	164 (3)
O1—H1···N1	0.82	1.85	2.590 (3)	149

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉N₃O₃
M_r	255.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.117 (3), 6.769 (2), 20.842 (3)
β (°)	99.235 (2)
V (Å³)	1130.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.978, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	8933, 2469, 1283
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.153, 1.04
No. of reflections	2469
No. of parameters	176
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.902 (10)	2.020 (14)	2.898 (3)	164 (3)
O1—H1···N1	0.82	1.85	2.590 (3)	149

Symmetry code: (i) −x+1, −y, −z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bingöl Alpaslan, Y., Alpaslan, G., Ağar, A. & Işık, Ş. (2010). Acta Cryst. E66, o510. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Karadağ, A. T., Atalay, Ş. & Genç, H. (2011). Acta Cryst. E67, o95. Web of Science CrossRef IUCr Journals Google Scholar
Miura, Y., Aritake, Y. & Akitsu, T. (2009). Acta Cryst. E65, o2381. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, L., Cao, D. & Cui, J. (2010). Acta Cryst. E66, o2204. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o409

doi:10.1107/S1600536811001644

Open

access