Crystal structure of 4-[1-(2-hy-droxy-prop-yl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid.

In the title compound, C25H22N2O3, the central imidazole ring makes dihedral angles of 48.43 (10), 20.23 (10) and 75.38 (11)° with the benzene ring and the two phenyl rings, respectively. The phenyl ring adjacent to the N-bonded 2-hy-droxy-propyl group shows the greatest twist, presumably to minimize steric inter-actions. In the crystal, mol-ecules are linked by O-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network. In addition, C-H⋯π inter-actions are also observed.

Related literature

For similar structures and background to the biological properties of imidazole derivatives, see: Akkurt et al. (2013 ▸); Mohamed et al. (2013a ▸,b ▸). For the synthesis of the title compound, see: Mohamed et al. (2012 ▸).

Experimental

Crystal data

C25H22N2O3

M = 398.45

Triclinic,

a = 6.8710 (4) Å

b = 10.7188 (6) Å

c = 14.9178 (7) Å

α = 103.569 (4)°

β = 93.094 (4)°

γ = 105.878 (5)°

V = 1019.03 (10) Å3

Z = 2

Cu Kα radiation

μ = 0.69 mm−1

T = 293 K

0.36 × 0.32 × 0.24 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.928, T max = 1.000

6591 measured reflections

3859 independent reflections

3209 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.02

3859 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027078/hb7338sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027078/hb7338Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027078/hb7338Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014027078/hb7338fig1.tif

Perspective view of the title mol­ecule with 50% probability ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S2056989014027078/hb7338fig2.tif

View of a part of the hydrogen bonding in the title compound

CCDC reference: 1038591

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H22N2O3	Z = 2
Mr = 398.45	F(000) = 420
Triclinic, P1	Dx = 1.299 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.8710 (4) Å	Cell parameters from 2716 reflections
b = 10.7188 (6) Å	θ = 4.7–70.9°
c = 14.9178 (7) Å	µ = 0.69 mm−1
α = 103.569 (4)°	T = 293 K
β = 93.094 (4)°	Irregular, colourless
γ = 105.878 (5)°	0.36 × 0.32 × 0.24 mm
V = 1019.03 (10) Å3

Agilent Xcalibur (Eos, Gemini) diffractometer	3859 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.0416 pixels mm-1	θmax = 71.3°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −13→11
Tmin = 0.928, Tmax = 1.000	l = −15→18
6591 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.2833P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3859 reflections	Δρmax = 0.25 e Å−3
274 parameters	Δρmin = −0.25 e Å−3

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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
O1	0.8499 (3)	1.73494 (13)	0.98882 (10)	0.0517 (5)
O2	0.8373 (2)	1.64288 (12)	1.10828 (8)	0.0388 (4)
O3	0.02746 (18)	1.11133 (11)	0.77597 (8)	0.0320 (3)
N1	0.6209 (2)	1.07389 (14)	0.70106 (10)	0.0308 (4)
N2	0.3691 (2)	0.99670 (14)	0.77918 (10)	0.0303 (4)
C1	0.5243 (2)	1.10427 (16)	0.77304 (11)	0.0296 (5)
C2	0.3686 (3)	0.89049 (17)	0.70448 (12)	0.0307 (5)
C3	0.5245 (3)	0.93989 (17)	0.65689 (12)	0.0304 (5)
C4	0.5945 (3)	0.87422 (17)	0.57186 (12)	0.0323 (5)
C5	0.5483 (3)	0.73492 (19)	0.53904 (14)	0.0420 (6)
C6	0.6122 (3)	0.6785 (2)	0.45708 (15)	0.0480 (6)
C7	0.7243 (3)	0.7582 (2)	0.40643 (13)	0.0441 (6)
C8	0.7719 (3)	0.8962 (2)	0.43826 (13)	0.0421 (6)
C9	0.7082 (3)	0.95396 (19)	0.52012 (13)	0.0376 (6)
C10	0.5889 (2)	1.23891 (17)	0.83951 (12)	0.0306 (5)
C11	0.6297 (3)	1.35063 (18)	0.80399 (12)	0.0355 (5)
C12	0.7025 (3)	1.47865 (18)	0.86269 (12)	0.0357 (5)
C13	0.7361 (2)	1.49682 (16)	0.95828 (12)	0.0303 (5)
C14	0.6976 (3)	1.38537 (18)	0.99390 (12)	0.0338 (5)
C15	0.6249 (3)	1.25733 (17)	0.93528 (12)	0.0338 (5)
C16	0.8137 (3)	1.63675 (17)	1.01870 (12)	0.0337 (5)
C17	0.2157 (3)	0.99226 (18)	0.84355 (12)	0.0335 (5)
C18	0.0062 (3)	0.98690 (17)	0.80001 (13)	0.0332 (5)
C19	−0.1480 (3)	0.9614 (2)	0.86693 (15)	0.0434 (6)
C20	0.2276 (3)	0.75300 (17)	0.69024 (12)	0.0333 (5)
C21	0.0656 (3)	0.70164 (19)	0.61958 (14)	0.0434 (6)
C22	−0.0584 (3)	0.5708 (2)	0.60422 (17)	0.0544 (7)
C23	−0.0218 (4)	0.4910 (2)	0.65886 (17)	0.0563 (7)
C24	0.1364 (4)	0.5410 (2)	0.72990 (16)	0.0581 (8)
C25	0.2614 (4)	0.6721 (2)	0.74577 (14)	0.0465 (6)
H2	0.88300	1.72160	1.13820	0.0580*
H3	−0.08050	1.10880	0.74830	0.0480*
H5	0.47390	0.67970	0.57260	0.0500*
H6	0.57920	0.58550	0.43580	0.0580*
H7	0.76740	0.71960	0.35150	0.0530*
H8	0.84730	0.95070	0.40450	0.0500*
H9	0.74160	1.04700	0.54090	0.0450*
H11	0.60790	1.33940	0.74010	0.0430*
H12	0.72910	1.55290	0.83810	0.0430*
H14	0.72080	1.39670	1.05770	0.0410*
H15	0.60000	1.18320	0.95980	0.0410*
H17A	0.26330	1.07110	0.89580	0.0400*
H17B	0.20180	0.91390	0.86740	0.0400*
H18	−0.03550	0.91320	0.74320	0.0400*
H19A	−0.10920	1.03390	0.92250	0.0650*
H19B	−0.15270	0.87860	0.88230	0.0650*
H19C	−0.28010	0.95570	0.83860	0.0650*
H21	0.04000	0.75520	0.58230	0.0520*
H22	−0.16690	0.53690	0.55670	0.0650*
H23	−0.10430	0.40290	0.64770	0.0680*
H24	0.15990	0.48720	0.76740	0.0700*
H25	0.36850	0.70580	0.79400	0.0560*

	U11	U22	U33	U12	U13	U23
O1	0.0798 (11)	0.0273 (7)	0.0409 (8)	0.0080 (7)	−0.0013 (7)	0.0064 (6)
O2	0.0508 (8)	0.0250 (6)	0.0327 (7)	0.0062 (6)	−0.0012 (6)	−0.0002 (5)
O3	0.0303 (6)	0.0279 (6)	0.0335 (6)	0.0054 (5)	−0.0004 (5)	0.0044 (5)
N1	0.0295 (7)	0.0261 (7)	0.0316 (7)	0.0062 (6)	−0.0012 (6)	0.0011 (6)
N2	0.0271 (7)	0.0277 (7)	0.0318 (7)	0.0083 (6)	−0.0001 (6)	0.0004 (6)
C1	0.0285 (8)	0.0264 (8)	0.0301 (8)	0.0086 (7)	−0.0027 (6)	0.0010 (7)
C2	0.0289 (8)	0.0272 (8)	0.0316 (8)	0.0089 (7)	−0.0031 (7)	0.0000 (7)
C3	0.0295 (8)	0.0278 (8)	0.0300 (8)	0.0087 (7)	−0.0036 (7)	0.0013 (7)
C4	0.0300 (8)	0.0329 (9)	0.0308 (8)	0.0104 (7)	−0.0017 (7)	0.0019 (7)
C5	0.0448 (11)	0.0330 (10)	0.0435 (10)	0.0099 (8)	0.0077 (8)	0.0023 (8)
C6	0.0527 (12)	0.0353 (10)	0.0472 (11)	0.0131 (9)	0.0046 (9)	−0.0060 (9)
C7	0.0427 (11)	0.0521 (12)	0.0329 (9)	0.0197 (9)	0.0014 (8)	−0.0039 (8)
C8	0.0394 (10)	0.0502 (12)	0.0367 (10)	0.0144 (9)	0.0055 (8)	0.0098 (8)
C9	0.0375 (10)	0.0352 (10)	0.0375 (10)	0.0113 (8)	0.0022 (8)	0.0042 (8)
C10	0.0252 (8)	0.0271 (8)	0.0337 (9)	0.0069 (6)	−0.0005 (6)	−0.0012 (7)
C11	0.0378 (9)	0.0335 (9)	0.0293 (9)	0.0071 (7)	0.0005 (7)	0.0020 (7)
C12	0.0403 (10)	0.0277 (9)	0.0361 (9)	0.0063 (7)	0.0019 (7)	0.0078 (7)
C13	0.0275 (8)	0.0268 (8)	0.0327 (9)	0.0078 (7)	0.0008 (7)	0.0012 (7)
C14	0.0370 (9)	0.0318 (9)	0.0284 (8)	0.0092 (7)	−0.0004 (7)	0.0018 (7)
C15	0.0371 (9)	0.0257 (8)	0.0353 (9)	0.0074 (7)	−0.0001 (7)	0.0047 (7)
C16	0.0352 (9)	0.0282 (9)	0.0343 (9)	0.0086 (7)	0.0011 (7)	0.0031 (7)
C17	0.0334 (9)	0.0302 (9)	0.0341 (9)	0.0094 (7)	0.0044 (7)	0.0028 (7)
C18	0.0313 (9)	0.0247 (8)	0.0401 (9)	0.0073 (7)	0.0018 (7)	0.0034 (7)
C19	0.0382 (10)	0.0434 (11)	0.0510 (12)	0.0111 (8)	0.0069 (9)	0.0174 (9)
C20	0.0344 (9)	0.0275 (8)	0.0336 (9)	0.0078 (7)	0.0063 (7)	0.0009 (7)
C21	0.0417 (11)	0.0324 (10)	0.0481 (11)	0.0083 (8)	−0.0020 (9)	−0.0002 (8)
C22	0.0411 (11)	0.0385 (11)	0.0647 (14)	−0.0005 (9)	0.0001 (10)	−0.0065 (10)
C23	0.0623 (14)	0.0296 (10)	0.0615 (14)	−0.0034 (9)	0.0226 (11)	−0.0010 (10)
C24	0.0905 (18)	0.0328 (11)	0.0473 (12)	0.0096 (11)	0.0154 (12)	0.0118 (9)
C25	0.0608 (13)	0.0348 (10)	0.0378 (10)	0.0094 (9)	0.0005 (9)	0.0047 (8)

O1—C16	1.207 (2)	C18—C19	1.509 (3)
O2—C16	1.321 (2)	C20—C25	1.385 (3)
O3—C18	1.433 (2)	C20—C21	1.385 (3)
N1—C1	1.316 (2)	C21—C22	1.386 (3)
N1—C3	1.387 (2)	C22—C23	1.372 (3)
N2—C1	1.365 (2)	C23—C24	1.372 (4)
N2—C2	1.393 (2)	C24—C25	1.389 (3)
N2—C17	1.462 (2)	C5—H5	0.9300
O2—H2	0.8200	C6—H6	0.9300
O3—H3	0.8200	C7—H7	0.9300
C1—C10	1.481 (2)	C8—H8	0.9300
C2—C20	1.485 (3)	C9—H9	0.9300
C2—C3	1.371 (3)	C11—H11	0.9300
C3—C4	1.472 (3)	C12—H12	0.9300
C4—C9	1.395 (3)	C14—H14	0.9300
C4—C5	1.397 (3)	C15—H15	0.9300
C5—C6	1.382 (3)	C17—H17A	0.9700
C6—C7	1.378 (3)	C17—H17B	0.9700
C7—C8	1.382 (3)	C18—H18	0.9800
C8—C9	1.385 (3)	C19—H19A	0.9600
C10—C15	1.394 (2)	C19—H19B	0.9600
C10—C11	1.387 (3)	C19—H19C	0.9600
C11—C12	1.383 (3)	C21—H21	0.9300
C12—C13	1.391 (2)	C22—H22	0.9300
C13—C14	1.386 (3)	C23—H23	0.9300
C13—C16	1.491 (2)	C24—H24	0.9300
C14—C15	1.383 (3)	C25—H25	0.9300
C17—C18	1.528 (3)
C1—N1—C3	106.24 (15)	C22—C23—C24	120.1 (2)
C1—N2—C2	106.50 (14)	C23—C24—C25	120.0 (2)
C1—N2—C17	128.48 (15)	C20—C25—C24	120.4 (2)
C2—N2—C17	124.71 (15)	C4—C5—H5	120.00
C16—O2—H2	109.00	C6—C5—H5	120.00
C18—O3—H3	109.00	C5—C6—H6	120.00
N1—C1—N2	111.74 (15)	C7—C6—H6	120.00
N1—C1—C10	122.02 (15)	C6—C7—H7	120.00
N2—C1—C10	126.19 (14)	C8—C7—H7	120.00
N2—C2—C3	106.17 (16)	C7—C8—H8	120.00
C3—C2—C20	131.12 (17)	C9—C8—H8	120.00
N2—C2—C20	122.60 (16)	C4—C9—H9	120.00
N1—C3—C4	120.13 (17)	C8—C9—H9	120.00
N1—C3—C2	109.35 (16)	C10—C11—H11	120.00
C2—C3—C4	130.52 (17)	C12—C11—H11	120.00
C3—C4—C9	118.87 (16)	C11—C12—H12	120.00
C3—C4—C5	123.02 (17)	C13—C12—H12	120.00
C5—C4—C9	118.10 (17)	C13—C14—H14	120.00
C4—C5—C6	120.58 (19)	C15—C14—H14	120.00
C5—C6—C7	120.9 (2)	C10—C15—H15	120.00
C6—C7—C8	119.21 (19)	C14—C15—H15	120.00
C7—C8—C9	120.50 (19)	N2—C17—H17A	109.00
C4—C9—C8	120.76 (18)	N2—C17—H17B	109.00
C11—C10—C15	119.05 (16)	C18—C17—H17A	109.00
C1—C10—C11	118.17 (15)	C18—C17—H17B	109.00
C1—C10—C15	122.60 (16)	H17A—C17—H17B	108.00
C10—C11—C12	120.58 (16)	O3—C18—H18	109.00
C11—C12—C13	120.27 (17)	C17—C18—H18	109.00
C12—C13—C16	118.27 (16)	C19—C18—H18	109.00
C12—C13—C14	119.29 (16)	C18—C19—H19A	109.00
C14—C13—C16	122.44 (16)	C18—C19—H19B	109.00
C13—C14—C15	120.49 (16)	C18—C19—H19C	109.00
C10—C15—C14	120.32 (17)	H19A—C19—H19B	109.00
O2—C16—C13	113.42 (15)	H19A—C19—H19C	109.00
O1—C16—C13	123.33 (16)	H19B—C19—H19C	110.00
O1—C16—O2	123.25 (17)	C20—C21—H21	120.00
N2—C17—C18	113.88 (14)	C22—C21—H21	120.00
O3—C18—C17	107.26 (15)	C21—C22—H22	120.00
O3—C18—C19	112.97 (16)	C23—C22—H22	120.00
C17—C18—C19	109.78 (16)	C22—C23—H23	120.00
C2—C20—C21	120.99 (17)	C24—C23—H23	120.00
C21—C20—C25	118.92 (18)	C23—C24—H24	120.00
C2—C20—C25	120.05 (18)	C25—C24—H24	120.00
C20—C21—C22	120.29 (19)	C20—C25—H25	120.00
C21—C22—C23	120.3 (2)	C24—C25—H25	120.00
C3—N1—C1—N2	0.37 (19)	C5—C4—C9—C8	0.4 (3)
C3—N1—C1—C10	177.80 (15)	C3—C4—C5—C6	177.8 (2)
C1—N1—C3—C4	179.15 (17)	C9—C4—C5—C6	−0.7 (3)
C1—N1—C3—C2	−0.4 (2)	C4—C5—C6—C7	0.6 (3)
C17—N2—C1—N1	−173.96 (16)	C5—C6—C7—C8	−0.3 (3)
C2—N2—C1—N1	−0.23 (19)	C6—C7—C8—C9	0.1 (3)
C17—N2—C2—C20	−9.4 (3)	C7—C8—C9—C4	−0.2 (3)
C2—N2—C1—C10	−177.53 (16)	C1—C10—C15—C14	175.83 (17)
C17—N2—C1—C10	8.7 (3)	C11—C10—C15—C14	0.9 (3)
C1—N2—C2—C20	176.53 (17)	C15—C10—C11—C12	−0.9 (3)
C1—N2—C2—C3	0.0 (2)	C1—C10—C11—C12	−176.03 (17)
C17—N2—C2—C3	174.02 (17)	C10—C11—C12—C13	0.1 (3)
C2—N2—C17—C18	−69.5 (2)	C11—C12—C13—C16	−179.71 (18)
C1—N2—C17—C18	103.2 (2)	C11—C12—C13—C14	0.6 (3)
N2—C1—C10—C15	49.3 (2)	C12—C13—C16—O1	−0.4 (3)
N1—C1—C10—C11	47.3 (2)	C12—C13—C16—O2	179.00 (17)
N1—C1—C10—C15	−127.74 (19)	C14—C13—C16—O1	179.3 (2)
N2—C1—C10—C11	−135.71 (18)	C14—C13—C16—O2	−1.3 (3)
N2—C2—C3—N1	0.2 (2)	C12—C13—C14—C15	−0.5 (3)
N2—C2—C20—C21	108.0 (2)	C16—C13—C14—C15	179.75 (18)
C20—C2—C3—C4	4.7 (4)	C13—C14—C15—C10	−0.2 (3)
C3—C2—C20—C25	101.1 (3)	N2—C17—C18—O3	−65.48 (19)
N2—C2—C3—C4	−179.22 (19)	N2—C17—C18—C19	171.44 (16)
C20—C2—C3—N1	−175.90 (19)	C2—C20—C21—C22	176.72 (19)
N2—C2—C20—C25	−74.5 (3)	C25—C20—C21—C22	−0.9 (3)
C3—C2—C20—C21	−76.4 (3)	C2—C20—C25—C24	−176.7 (2)
N1—C3—C4—C5	160.89 (19)	C21—C20—C25—C24	0.9 (3)
C2—C3—C4—C9	158.7 (2)	C20—C21—C22—C23	0.0 (3)
N1—C3—C4—C9	−20.7 (3)	C21—C22—C23—C24	0.9 (4)
C2—C3—C4—C5	−19.7 (3)	C22—C23—C24—C25	−0.9 (4)
C3—C4—C9—C8	−178.07 (19)	C23—C24—C25—C20	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.82	1.86	2.6718 (17)	170
O3—H3···N1ii	0.82	2.04	2.8377 (19)	166
C19—H19B···O1iii	0.96	2.46	3.355 (3)	155
C24—H24···O2iv	0.93	2.57	3.482 (3)	167
C19—H19C···Cg1ii	0.96	2.53	3.422 (2)	154

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the N1/N2/C1C3 ring.

DHA	DH	HA	D A	DHA
O2H2O3i	0.82	1.86	2.6718(17)	170
O3H3N1ii	0.82	2.04	2.8377(19)	166
C19H19BO1iii	0.96	2.46	3.355(3)	155
C24H24O2iv	0.93	2.57	3.482(3)	167
C19H19C Cg1ii	0.96	2.53	3.422(2)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .