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In the title compound, C13H10N2O, the benzimidazole system is nearly coplanar with the phenol ring, with a small dihedral angle of 8.11 (5)°. Inter­molecular N—H...O and O—H...N hydrogen bonding helps to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033612/xu2292sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033612/xu2292Isup2.hkl
Contains datablock I

CCDC reference: 657743

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.103
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

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Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The ligands containing benzimidazolyl substituent(s), which could provide hydrogen bond donor NH groups and π-π stacking interaction, have being extensively investigated now (Cai, Chen et al., 2003). As a part of the structural studies of benzimidazolyl series (Cai et al., 2002; Cai, Su et al. 2003) here we report the synthesis and structure of the title compound.

Fig. 1 shows an ORTEP diagram of the compound together with the atom numbering scheme. The benzimidazolyl ring is almost coplanar to phenol ring with 8.11 (1)° of dihedral angle in the molecule. The dihedral angle between two perpendicular sheet-like molecules is 86.19 (6)° in the crystal structure, which are connected by hydrogen bondings N—H···O [O···N 2.856 (1) Å, H···O 2.012 (2) Å, N—H···O 158.8 (1)° [symmetry code: x - 1/2,-y + 1/2,z + 1/2] and O—H···N [O···N 2.652 (1) Å, H···O 1.843 (1) Å, O—H···N 173.5 (2)° [symmetry code: x - 1/2,-y + 1/2,z - 1/2] to form an infinite wave-like two-dimensional layer, while the three-dimensional network structure is constructed by face-to-face π-π stacking interaction, the shortest distance between benzimidazole ring and phenol ring is 3.554 Å.

Related literature top

For general background, see Cai, Chen et al. (2003). For related structures, see Cai, Su et al. (2003); Su et al. (2002).

For related literature, see: Cai (2002).

Experimental top

To phenylenediamine (3.67 g, 0.034 mol) in propylene glycol (50 ml) was added 4-hydroxybenzoic acid (4.69 g, 0.034 mol), and the solution refluxed for 24 h and then cooled to room temperature. Ice cold water (50 ml) was then added to force the precipitation of a brown solid which was collected and dissolved in hot methanol. The solution is filtered over activated carbon and the filtrate was allowed to evaporate slowly to give single crystals (yield 6.15 g, 86%).

Refinement top

H atoms on C and O atoms were placed in idealized positions, and refined in riding mode with Uiso(H) = 1.2Ueq(C) or Uiso(O). H atom on N atom was located in a difference Fourier map and refined isotropically.

Structure description top

The ligands containing benzimidazolyl substituent(s), which could provide hydrogen bond donor NH groups and π-π stacking interaction, have being extensively investigated now (Cai, Chen et al., 2003). As a part of the structural studies of benzimidazolyl series (Cai et al., 2002; Cai, Su et al. 2003) here we report the synthesis and structure of the title compound.

Fig. 1 shows an ORTEP diagram of the compound together with the atom numbering scheme. The benzimidazolyl ring is almost coplanar to phenol ring with 8.11 (1)° of dihedral angle in the molecule. The dihedral angle between two perpendicular sheet-like molecules is 86.19 (6)° in the crystal structure, which are connected by hydrogen bondings N—H···O [O···N 2.856 (1) Å, H···O 2.012 (2) Å, N—H···O 158.8 (1)° [symmetry code: x - 1/2,-y + 1/2,z + 1/2] and O—H···N [O···N 2.652 (1) Å, H···O 1.843 (1) Å, O—H···N 173.5 (2)° [symmetry code: x - 1/2,-y + 1/2,z - 1/2] to form an infinite wave-like two-dimensional layer, while the three-dimensional network structure is constructed by face-to-face π-π stacking interaction, the shortest distance between benzimidazole ring and phenol ring is 3.554 Å.

For general background, see Cai, Chen et al. (2003). For related structures, see Cai, Su et al. (2003); Su et al. (2002).

For related literature, see: Cai (2002).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of title molecule. The atom-numbering scheme is shown at the 30% probability level.
[Figure 2] Fig. 2. A view of the molecular network parallel to (101)
4-(1H-Benzo[d]imidazol-2-yl)phenol top
Crystal data top
C13H10N2OF(000) = 440
Mr = 210.23Dx = 1.298 Mg m3
Monoclinic, P21/nMelting point: 508 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.1679 (3) ÅCell parameters from 5172 reflections
b = 15.1517 (6) Åθ = 2.4–27.5°
c = 9.9079 (4) ŵ = 0.09 mm1
β = 90.556 (2)°T = 298 K
V = 1076.01 (8) Å3Block, colourless
Z = 40.22 × 0.17 × 0.13 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2092 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
φ and ω scansh = 99
10089 measured reflectionsk = 1915
2464 independent reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1927P]
where P = (Fo2 + 2Fc2)/3
2464 reflections(Δ/σ)max < 0.001
149 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.17 e Å3
Crystal data top
C13H10N2OV = 1076.01 (8) Å3
Mr = 210.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.1679 (3) ŵ = 0.09 mm1
b = 15.1517 (6) ÅT = 298 K
c = 9.9079 (4) Å0.22 × 0.17 × 0.13 mm
β = 90.556 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2092 reflections with I > 2σ(I)
10089 measured reflectionsRint = 0.019
2464 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.16 e Å3
2464 reflectionsΔρmin = 0.17 e Å3
149 parameters
Special details top

Experimental. The assigned structure was substantiated by EA and MS data. Elemental analysis calculated for C13H10N2O: C, 74.27; H, 4.79; N, 13.33; found: C, 73.98; H, 4.87; N, 13.28. FAB-MS m/z (%): 211(M++1, 68), 210(M+, 100).

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
xyzUiso*/Ueq
O10.12380 (10)0.35627 (6)0.15835 (9)0.0498 (2)
H1A0.01850.37600.14620.075*
N20.29490 (13)0.06719 (6)0.61996 (10)0.0455 (2)
N10.01358 (12)0.06759 (6)0.63364 (10)0.0406 (2)
C10.24064 (16)0.00742 (8)0.71879 (12)0.0460 (3)
C20.3466 (2)0.04686 (10)0.80335 (16)0.0646 (4)
H20.47610.04770.79840.078*
C30.2541 (2)0.09910 (10)0.89419 (16)0.0691 (4)
H30.32250.13600.95110.083*
C40.0615 (2)0.09817 (9)0.90314 (14)0.0614 (4)
H40.00360.13440.96590.074*
C50.04601 (19)0.04497 (9)0.82150 (13)0.0522 (3)
H50.17540.04420.82780.063*
C60.04717 (15)0.00766 (7)0.72905 (11)0.0412 (3)
C70.13874 (14)0.10192 (7)0.57169 (11)0.0381 (2)
C80.12968 (14)0.16878 (7)0.46561 (10)0.0381 (2)
C90.29061 (15)0.19137 (8)0.39541 (12)0.0448 (3)
H90.40290.16390.41750.054*
C100.28632 (15)0.25331 (8)0.29430 (12)0.0467 (3)
H100.39530.26710.24870.056*
C110.12059 (15)0.29563 (8)0.25943 (11)0.0407 (3)
C120.04087 (15)0.27377 (8)0.32846 (12)0.0446 (3)
H120.15280.30160.30650.054*
C130.03603 (15)0.21105 (8)0.42931 (11)0.0435 (3)
H130.14550.19670.47390.052*
H10.1306 (13)0.0848 (9)0.6208 (13)0.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0285 (4)0.0655 (6)0.0555 (5)0.0017 (4)0.0022 (3)0.0137 (4)
N20.0315 (5)0.0487 (5)0.0563 (6)0.0007 (4)0.0027 (4)0.0007 (4)
N10.0295 (5)0.0450 (5)0.0473 (5)0.0007 (4)0.0001 (4)0.0024 (4)
C10.0390 (6)0.0444 (6)0.0546 (7)0.0011 (5)0.0036 (5)0.0013 (5)
C20.0470 (7)0.0663 (9)0.0804 (10)0.0077 (6)0.0102 (7)0.0127 (7)
C30.0730 (10)0.0614 (9)0.0727 (9)0.0062 (7)0.0139 (8)0.0164 (7)
C40.0737 (9)0.0539 (8)0.0567 (7)0.0047 (7)0.0002 (7)0.0068 (6)
C50.0504 (7)0.0523 (7)0.0540 (7)0.0044 (5)0.0037 (5)0.0011 (6)
C60.0399 (6)0.0391 (5)0.0445 (6)0.0003 (4)0.0018 (4)0.0066 (4)
C70.0302 (5)0.0402 (6)0.0438 (5)0.0007 (4)0.0012 (4)0.0090 (4)
C80.0320 (5)0.0418 (6)0.0405 (5)0.0017 (4)0.0009 (4)0.0065 (4)
C90.0281 (5)0.0536 (7)0.0525 (6)0.0035 (4)0.0005 (4)0.0002 (5)
C100.0272 (5)0.0599 (7)0.0532 (6)0.0010 (5)0.0049 (4)0.0041 (5)
C110.0309 (5)0.0489 (6)0.0422 (6)0.0023 (4)0.0010 (4)0.0020 (5)
C120.0269 (5)0.0573 (7)0.0497 (6)0.0031 (5)0.0001 (4)0.0025 (5)
C130.0284 (5)0.0554 (7)0.0467 (6)0.0011 (4)0.0036 (4)0.0002 (5)
Geometric parameters (Å, º) top
O1—C111.3595 (14)C4—H40.9300
O1—H1A0.8200C5—C61.3902 (17)
N2—C71.3221 (14)C5—H50.9300
N2—C11.3920 (15)C7—C81.4609 (16)
N1—C71.3610 (14)C8—C131.3935 (15)
N1—C61.3784 (15)C8—C91.3953 (15)
N1—H10.886 (8)C9—C101.3728 (17)
C1—C61.3915 (16)C9—H90.9300
C1—C21.3939 (18)C10—C111.3906 (15)
C2—C31.374 (2)C10—H100.9300
C2—H20.9300C11—C121.3901 (15)
C3—C41.384 (2)C12—C131.3792 (16)
C3—H30.9300C12—H120.9300
C4—C51.3733 (19)C13—H130.9300
C11—O1—H1A109.5C5—C6—C1122.15 (11)
C7—N2—C1105.79 (9)N2—C7—N1111.40 (10)
C7—N1—C6108.16 (9)N2—C7—C8124.60 (10)
C7—N1—H1125.8 (9)N1—C7—C8124.00 (9)
C6—N1—H1125.8 (9)C13—C8—C9117.74 (11)
C6—C1—N2109.58 (10)C13—C8—C7122.42 (10)
C6—C1—C2119.69 (12)C9—C8—C7119.83 (10)
N2—C1—C2130.72 (12)C10—C9—C8121.24 (10)
C3—C2—C1118.03 (13)C10—C9—H9119.4
C3—C2—H2121.0C8—C9—H9119.4
C1—C2—H2121.0C9—C10—C11120.63 (10)
C2—C3—C4121.61 (13)C9—C10—H10119.7
C2—C3—H3119.2C11—C10—H10119.7
C4—C3—H3119.2O1—C11—C12122.93 (10)
C5—C4—C3121.50 (14)O1—C11—C10118.30 (10)
C5—C4—H4119.2C12—C11—C10118.76 (11)
C3—C4—H4119.2C13—C12—C11120.36 (10)
C4—C5—C6117.02 (13)C13—C12—H12119.8
C4—C5—H5121.5C11—C12—H12119.8
C6—C5—H5121.5C12—C13—C8121.27 (10)
N1—C6—C5132.78 (11)C12—C13—H13119.4
N1—C6—C1105.07 (10)C8—C13—H13119.4
C7—N2—C1—C60.36 (13)C6—N1—C7—N20.72 (12)
C7—N2—C1—C2179.12 (14)C6—N1—C7—C8179.15 (9)
C6—C1—C2—C30.4 (2)N2—C7—C8—C13172.12 (11)
N2—C1—C2—C3179.05 (13)N1—C7—C8—C137.74 (16)
C1—C2—C3—C40.4 (2)N2—C7—C8—C98.78 (16)
C2—C3—C4—C50.0 (2)N1—C7—C8—C9171.36 (10)
C3—C4—C5—C60.3 (2)C13—C8—C9—C100.21 (17)
C7—N1—C6—C5178.88 (12)C7—C8—C9—C10179.36 (11)
C7—N1—C6—C10.89 (12)C8—C9—C10—C110.26 (19)
C4—C5—C6—N1179.96 (12)C9—C10—C11—O1179.84 (11)
C4—C5—C6—C10.23 (18)C9—C10—C11—C120.28 (18)
N2—C1—C6—N10.77 (13)O1—C11—C12—C13179.35 (11)
C2—C1—C6—N1179.70 (12)C10—C11—C12—C130.18 (18)
N2—C1—C6—C5179.02 (10)C11—C12—C13—C80.67 (18)
C2—C1—C6—C50.10 (18)C9—C8—C13—C120.68 (17)
C1—N2—C7—N10.22 (12)C7—C8—C13—C12179.80 (10)
C1—N2—C7—C8179.65 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N2i0.821.842.6515 (12)174
N1—H1···O1ii0.89 (1)2.01 (1)2.8564 (12)159 (1)
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H10N2O
Mr210.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.1679 (3), 15.1517 (6), 9.9079 (4)
β (°) 90.556 (2)
V3)1076.01 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.22 × 0.17 × 0.13
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10089, 2464, 2092
Rint0.019
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.103, 1.04
No. of reflections2464
No. of parameters149
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.17

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N2i0.821.842.6515 (12)174
N1—H1···O1ii0.886 (8)2.012 (9)2.8564 (12)158.8 (12)
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x1/2, y+1/2, z+1/2.
 

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