Crystal structure and Hirshfeld surface analysis of a new benzimidazole compound, 3-{1-[(2-hy­droxyphen­yl)meth­yl]-1H-1,3-benzo­diazol-2-yl}phenol

In the title compound, the benzimidazole moiety subtends dihedral angles of 46.16 (7) and 77.45 (8)° with the benzene rings, which themselves form a dihedral angle of 54.34 (9)°. The crystal structure features O—H...N and O—H...O hydrogen-bonding inter­actions, which together lead to the formation of two-dimensional hydrogen-bonded layers parallel to the (101) plane, as well as π–π inter­actions

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.190
• Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
                1  1  0,   0  2  0,  -1  0  1,   1  0  1,  -1  1  1,   0  1  1,
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         23 Report
                2  0  0,   1  2  0,   2  2  0,   1  3  0,  -2  1  1,   2  1  1,
               -2  2  1,   0  2  1,   1  2  1,   2  2  1,  -2  3  1,  -1  3  1,
                0  3  1,  -2  0  2,   0  0  2,  -2  1  2,   1  1  2,  -1  2  2,
                0  2  2,  -1  3  2,   0  3  2,  -1  0  3,   0  1  3,

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
              H1    H2
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.10 Report
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
                2  0  0,
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          3 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

3-{1-[(2-Hydroxyphenyl)methyl]-1H-1,3-benzodiazol-2-yl}phenol

Crystal data

C20H16N2O2	F(000) = 664
Mr = 316.35	Least Squares Treatment of 25 SET4 setting angles.
Monoclinic, P21/n	Dx = 1.322 Mg m^−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.6474 (3) Å	Cell parameters from 33506 reflections
b = 13.2429 (3) Å	θ = 2.4–30.1°
c = 11.4176 (3) Å	µ = 0.09 mm^−1
β = 99.067 (1)°	T = 100 K
V = 1589.79 (7) Å^3	Prism, colourless
Z = 4	0.1 × 0.1 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	2866 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 30.1°, θmin = 2.4°
ω scans	h = −15→14
33506 measured reflections	k = −17→18
4650 independent reflections	l = −15→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.190	W = 1/[Σ^2(FO^2) + (0.1027P)^2 + 0.1399P] WHERE P = (FO^2 + 2FC^2)/3
S = 1.06	(Δ/σ)max < 0.001
4643 reflections	Δρmax = 0.50 e Å^−3
217 parameters	Δρmin = −0.30 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.71485 (14)	0.50588 (12)	0.85134 (15)	0.0674 (6)
O2	0.86823 (12)	0.19463 (10)	0.75574 (10)	0.0484 (4)
N1	0.50090 (14)	0.18753 (11)	1.12414 (12)	0.0415 (4)
N2	0.64015 (13)	0.13212 (10)	1.01162 (12)	0.0365 (4)
C1	0.54208 (16)	0.30396 (13)	0.96699 (14)	0.0393 (5)
C2	0.64184 (18)	0.36170 (13)	0.93853 (15)	0.0434 (5)
C3	0.61480 (19)	0.45154 (14)	0.87656 (16)	0.0470 (6)
C4	0.49058 (19)	0.48277 (14)	0.84368 (16)	0.0496 (6)
C5	0.3922 (2)	0.42579 (16)	0.87286 (17)	0.0524 (6)
C6	0.41675 (19)	0.33701 (15)	0.93432 (16)	0.0475 (6)
C7	0.56219 (15)	0.20898 (13)	1.03474 (14)	0.0376 (5)
C8	0.62905 (16)	0.05631 (12)	1.09273 (15)	0.0386 (5)
C9	0.54146 (16)	0.09200 (13)	1.16216 (15)	0.0405 (5)
C10	0.50993 (19)	0.03349 (15)	1.25517 (17)	0.0504 (6)
C11	0.5675 (2)	−0.05921 (16)	1.27507 (19)	0.0584 (7)
C12	0.6536 (2)	−0.09453 (14)	1.20405 (19)	0.0573 (7)
C13	0.68637 (19)	−0.03791 (14)	1.11183 (17)	0.0485 (6)
C14	0.71836 (15)	0.12707 (14)	0.91676 (14)	0.0389 (5)
C15	0.85421 (16)	0.16113 (12)	0.95674 (14)	0.0353 (5)
C16	0.91028 (19)	0.16091 (16)	1.07445 (16)	0.0500 (6)
C17	1.0337 (2)	0.19263 (17)	1.10898 (18)	0.0565 (7)
C18	1.10283 (19)	0.22691 (18)	1.02536 (18)	0.0561 (7)
C19	1.04917 (17)	0.22814 (16)	0.90709 (17)	0.0505 (6)
C20	0.92539 (16)	0.19490 (12)	0.87220 (14)	0.0364 (5)
H1	0.69016	0.56161	0.82622	0.1010*
H2	0.90990	0.22934	0.71643	0.0730*
H2A	0.72555	0.34062	0.96058	0.0520*
H4	0.47340	0.54263	0.80161	0.0590*
H5	0.30871	0.44742	0.85090	0.0630*
H6	0.34993	0.29882	0.95425	0.0570*
H10	0.45194	0.05650	1.30205	0.0600*
H11	0.54868	−0.09918	1.33701	0.0700*
H12	0.68991	−0.15799	1.21930	0.0690*
H13	0.74390	−0.06162	1.06486	0.0580*
H14A	0.68017	0.16920	0.85120	0.0470*
H14B	0.71891	0.05813	0.88814	0.0470*
H16	0.86349	0.13880	1.13176	0.0600*
H17	1.06999	0.19081	1.18856	0.0680*
H18	1.18584	0.24933	1.04831	0.0670*
H19	1.09626	0.25138	0.85055	0.0610*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0589 (9)	0.0611 (9)	0.0872 (12)	0.0017 (7)	0.0269 (8)	0.0158 (8)
O2	0.0457 (7)	0.0684 (8)	0.0323 (6)	−0.0122 (6)	0.0096 (5)	0.0031 (5)
N1	0.0386 (8)	0.0533 (8)	0.0348 (7)	0.0000 (6)	0.0125 (6)	−0.0014 (6)
N2	0.0342 (7)	0.0432 (7)	0.0342 (7)	−0.0025 (6)	0.0118 (6)	−0.0014 (5)
C1	0.0426 (9)	0.0459 (9)	0.0300 (8)	0.0020 (7)	0.0080 (7)	−0.0044 (6)
C2	0.0446 (10)	0.0482 (9)	0.0383 (9)	0.0035 (8)	0.0092 (8)	−0.0003 (7)
C3	0.0536 (11)	0.0493 (10)	0.0407 (10)	−0.0016 (8)	0.0157 (8)	−0.0028 (7)
C4	0.0579 (12)	0.0499 (10)	0.0395 (10)	0.0095 (9)	0.0034 (8)	0.0003 (8)
C5	0.0495 (11)	0.0612 (11)	0.0446 (10)	0.0083 (9)	0.0012 (8)	−0.0028 (9)
C6	0.0458 (10)	0.0550 (10)	0.0418 (10)	0.0037 (8)	0.0072 (8)	−0.0037 (8)
C7	0.0346 (8)	0.0475 (9)	0.0312 (8)	−0.0019 (7)	0.0068 (6)	−0.0039 (6)
C8	0.0349 (8)	0.0438 (8)	0.0370 (9)	−0.0085 (7)	0.0058 (7)	−0.0033 (7)
C9	0.0365 (9)	0.0489 (9)	0.0371 (9)	−0.0074 (7)	0.0089 (7)	−0.0024 (7)
C10	0.0487 (11)	0.0623 (11)	0.0426 (10)	−0.0139 (9)	0.0146 (8)	0.0028 (8)
C11	0.0643 (13)	0.0582 (12)	0.0519 (12)	−0.0225 (10)	0.0063 (10)	0.0102 (9)
C12	0.0674 (14)	0.0410 (9)	0.0600 (12)	−0.0101 (9)	−0.0006 (10)	0.0029 (9)
C13	0.0506 (11)	0.0445 (9)	0.0505 (11)	−0.0031 (8)	0.0081 (9)	−0.0044 (8)
C14	0.0360 (9)	0.0501 (9)	0.0325 (8)	−0.0039 (7)	0.0117 (7)	−0.0054 (7)
C15	0.0343 (8)	0.0411 (8)	0.0317 (8)	0.0004 (6)	0.0085 (6)	−0.0022 (6)
C16	0.0484 (11)	0.0690 (12)	0.0331 (9)	−0.0117 (9)	0.0076 (8)	0.0055 (8)
C17	0.0517 (12)	0.0776 (14)	0.0362 (10)	−0.0147 (10)	−0.0051 (8)	0.0049 (9)
C18	0.0373 (10)	0.0784 (13)	0.0500 (11)	−0.0128 (9)	−0.0007 (8)	0.0048 (10)
C19	0.0382 (10)	0.0718 (12)	0.0432 (10)	−0.0084 (9)	0.0120 (8)	0.0076 (9)
C20	0.0370 (9)	0.0427 (8)	0.0304 (8)	0.0018 (7)	0.0077 (7)	−0.0008 (6)

Geometric parameters (Å, º)

O1—C3	1.354 (3)	C14—C15	1.515 (2)
O2—C20	1.372 (2)	C15—C20	1.392 (2)
N1—C7	1.326 (2)	C15—C16	1.382 (2)
N1—C9	1.384 (2)	C16—C17	1.377 (3)
O1—H1	0.8200	C17—C18	1.372 (3)
N2—C7	1.365 (2)	C18—C19	1.381 (3)
N2—C14	1.468 (2)	C19—C20	1.387 (3)
O2—H2	0.8200	C2—H2A	0.9300
N2—C8	1.384 (2)	C4—H4	0.9300
C1—C6	1.398 (3)	C5—H5	0.9300
C1—C2	1.388 (3)	C6—H6	0.9300
C1—C7	1.475 (2)	C10—H10	0.9300
C2—C3	1.391 (3)	C11—H11	0.9300
C3—C4	1.380 (3)	C12—H12	0.9300
C4—C5	1.374 (3)	C13—H13	0.9300
C5—C6	1.373 (3)	C14—H14A	0.9700
C8—C13	1.391 (2)	C14—H14B	0.9700
C8—C9	1.398 (2)	C16—H16	0.9300
C9—C10	1.398 (3)	C17—H17	0.9300
C10—C11	1.375 (3)	C18—H18	0.9300
C11—C12	1.397 (3)	C19—H19	0.9300
C12—C13	1.382 (3)
C7—N1—C9	105.67 (14)	C17—C18—C19	119.99 (19)
C3—O1—H1	109.00	C18—C19—C20	120.34 (18)
C7—N2—C14	127.55 (14)	C15—C20—C19	119.96 (15)
C8—N2—C14	125.38 (14)	O2—C20—C15	117.67 (15)
C7—N2—C8	107.03 (13)	O2—C20—C19	122.37 (15)
C20—O2—H2	109.00	C1—C2—H2A	120.00
C6—C1—C7	117.43 (16)	C3—C2—H2A	120.00
C2—C1—C6	119.90 (16)	C3—C4—H4	120.00
C2—C1—C7	122.65 (15)	C5—C4—H4	120.00
C1—C2—C3	119.05 (17)	C4—C5—H5	120.00
C2—C3—C4	120.49 (18)	C6—C5—H5	120.00
O1—C3—C2	117.14 (18)	C1—C6—H6	120.00
O1—C3—C4	122.37 (17)	C5—C6—H6	120.00
C3—C4—C5	120.27 (18)	C9—C10—H10	121.00
C4—C5—C6	120.21 (19)	C11—C10—H10	121.00
C1—C6—C5	120.08 (18)	C10—C11—H11	119.00
N1—C7—C1	122.56 (15)	C12—C11—H11	119.00
N1—C7—N2	112.15 (15)	C11—C12—H12	119.00
N2—C7—C1	125.24 (14)	C13—C12—H12	119.00
N2—C8—C13	132.39 (16)	C8—C13—H13	122.00
C9—C8—C13	121.99 (16)	C12—C13—H13	122.00
N2—C8—C9	105.62 (14)	N2—C14—H14A	109.00
C8—C9—C10	120.33 (16)	N2—C14—H14B	109.00
N1—C9—C8	109.52 (15)	C15—C14—H14A	109.00
N1—C9—C10	130.13 (16)	C15—C14—H14B	109.00
C9—C10—C11	117.80 (18)	H14A—C14—H14B	108.00
C10—C11—C12	121.29 (19)	C15—C16—H16	119.00
C11—C12—C13	121.90 (18)	C17—C16—H16	119.00
C8—C13—C12	116.69 (18)	C16—C17—H17	120.00
N2—C14—C15	112.94 (13)	C18—C17—H17	120.00
C16—C15—C20	118.44 (16)	C17—C18—H18	120.00
C14—C15—C16	122.54 (15)	C19—C18—H18	120.00
C14—C15—C20	119.02 (14)	C18—C19—H19	120.00
C15—C16—C17	121.63 (18)	C20—C19—H19	120.00
C16—C17—C18	119.63 (19)
C9—N1—C7—N2	0.45 (19)	C3—C4—C5—C6	−0.4 (3)
C9—N1—C7—C1	178.12 (15)	C4—C5—C6—C1	−0.3 (3)
C7—N1—C9—C8	−0.12 (19)	N2—C8—C9—N1	−0.25 (19)
C7—N1—C9—C10	178.39 (19)	N2—C8—C9—C10	−178.92 (16)
C8—N2—C7—N1	−0.62 (19)	C13—C8—C9—N1	179.53 (16)
C8—N2—C7—C1	−178.22 (15)	C13—C8—C9—C10	0.9 (3)
C14—N2—C7—N1	177.32 (15)	N2—C8—C13—C12	179.02 (18)
C14—N2—C7—C1	−0.3 (3)	C9—C8—C13—C12	−0.7 (3)
C7—N2—C8—C9	0.51 (18)	N1—C9—C10—C11	−178.49 (18)
C7—N2—C8—C13	−179.25 (19)	C8—C9—C10—C11	−0.1 (3)
C14—N2—C8—C9	−177.49 (15)	C9—C10—C11—C12	−0.7 (3)
C14—N2—C8—C13	2.8 (3)	C10—C11—C12—C13	0.9 (3)
C7—N2—C14—C15	94.94 (19)	C11—C12—C13—C8	−0.2 (3)
C8—N2—C14—C15	−87.5 (2)	N2—C14—C15—C16	22.2 (2)
C6—C1—C2—C3	−0.6 (3)	N2—C14—C15—C20	−157.17 (15)
C7—C1—C2—C3	−178.60 (16)	C14—C15—C16—C17	−179.68 (19)
C2—C1—C6—C5	0.8 (3)	C20—C15—C16—C17	−0.3 (3)
C7—C1—C6—C5	178.91 (17)	C14—C15—C20—O2	−0.6 (2)
C2—C1—C7—N1	134.27 (18)	C14—C15—C20—C19	178.84 (16)
C2—C1—C7—N2	−48.4 (2)	C16—C15—C20—O2	−179.98 (16)
C6—C1—C7—N1	−43.8 (2)	C16—C15—C20—C19	−0.6 (3)
C6—C1—C7—N2	133.60 (18)	C15—C16—C17—C18	1.0 (3)
C1—C2—C3—O1	179.55 (16)	C16—C17—C18—C19	−0.9 (3)
C1—C2—C3—C4	−0.1 (3)	C17—C18—C19—C20	0.0 (3)
O1—C3—C4—C5	−179.00 (18)	C18—C19—C20—O2	−179.92 (19)
C2—C3—C4—C5	0.6 (3)	C18—C19—C20—C15	0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	2.04	2.861 (2)	173
O2—H2···N1^ii	0.82	1.89	2.7124 (19)	178
C16—H16···N2	0.93	2.55	2.878 (2)	101

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