Crystal structure of 4-[1-(2-hy­droxy­prop­yl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid

Jasinski, J.P.; Mohamed, S.K.; Akkurt, M.; Abdelhamid, A.A.; Albayati, M.R.

doi:10.1107/S2056989014027078

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o77-o78

doi:10.1107/S2056989014027078

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Crystal structure of 4-[1-(2-hydroxypropyl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid

Jerry P. Jasinski,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Antar A. Abdelhamid ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Sohag University, Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 December 2014; accepted 10 December 2014; online 3 January 2015)

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-hydroxypropyl group shows the greatest twist, presumably to minimize steric interactions. In the crystal, molecules 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 interactions are also observed.

Keywords: crystal structure; 4-[1-(2-hydroxypropyl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid; imidazole ring; amino alcohol.

CCDC reference: 1038591

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₅H₂₂N₂O₃
M_r = 398.45
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.136
S = 1.02
3859 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N2/C1–C3 ring.

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⋯O2^iv	0.93	2.57	3.482 (3)	167
C19—H19C⋯Cg1ⁱⁱ	0.96	2.53	3.422 (2)	154
Symmetry codes: (i) -x+1, -y+3, -z+2; (ii) x-1, y, z; (iii) x-1, y-1, z; (iv) -x+1, -y+2, -z+2.

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 ).

Supporting information

CCDC reference: 1038591

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989014027078/hb7338sup1.cif

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

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

checkCIF report

Comment top

Following to our ongoing study on synthesis of imidazole based amino alcohols (Akkurt et al., 2013; Mohamed et al., 2013a,b) we herein report the synthesis and crystal structure of the title compound.

In the title compound, Fig. 1, the central 1H-imidazole ring (N1/N2/C1—C3) makes dihedral angles of 48.43 (10), 20.23 (10) and 75.38 (11)°, with the benzene ring (C10–C15) and two phenyl rings (C4–C9 and C20–C25), respectively. The dihedral angle between the (C4–C9 and C20–C25) phenyl rings is 69.94 (11)°. The (C10–C15) benzene ring forms dihedral angles of 36.05 (10) and 35.91 (10)° with two the phenyl rings (C4–C9 and C20–C25), respectively. The bond lengths are comparable to those reported for similar compounds reported in the literature (Akkurt et al., 2013; Mohamed et al., 2013a,b).

In the crystal, O—H···N, O—H···O and C—H···O hydrogen bonds link the adjacent molecules, into a three dimensional network structure (Table 1, Fig. 2). Furthermore, C—H···π interactions (Table 1) are also observed in the packing of the title compound.

Related literature top

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 top

The title compound has been prepared according to our reported method (Mohamed et al., 2012). Irregular colourless chunks of (I) were obtained by the slow evaporation method using ethanol as a solvent. M.p. 456 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); 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).

Figures top

	Fig. 1. Perspective view of the title molecule with 50% probability ellipsoids.
	Fig. 2. View of a part of the hydrogen bonding in the title compound

4-[1-(2-Hydroxypropyl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid top

Crystal data top

C₂₅H₂₂N₂O₃	Z = 2
M_r = 398.45	F(000) = 420
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0703P)² + 0.2833P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3859 reflections	Δρ_max = 0.25 e Å⁻³
274 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₅H₂₂N₂O₃	γ = 105.878 (5)°
M_r = 398.45	V = 1019.03 (10) Å³
Triclinic, P1	Z = 2
a = 6.8710 (4) Å	Cu Kα radiation
b = 10.7188 (6) Å	µ = 0.69 mm⁻¹
c = 14.9178 (7) Å	T = 293 K
α = 103.569 (4)°	0.36 × 0.32 × 0.24 mm
β = 93.094 (4)°

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	3859 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	3209 reflections with I > 2σ(I)
T_min = 0.928, T_max = 1.000	R_int = 0.022
6591 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
3859 reflections	Δρ_min = −0.25 e Å⁻³
274 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/N2/C1–C3 ring.

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···O2^iv	0.93	2.57	3.482 (3)	167
C19—H19C···Cg1ⁱⁱ	0.96	2.53	3.422 (2)	154

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/N2/C1–C3 ring.

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···O2^iv	0.93	2.57	3.482 (3)	167
C19—H19C···Cg1ⁱⁱ	0.96	2.53	3.422 (2)	154

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

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer. Also, SKM would like to thank Keene State College for providing all X-ray data and Manchester Metropolitan University for supporting this study.

References

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Volume 71| Part 2| February 2015| Pages o77-o78

doi:10.1107/S2056989014027078

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4-[1-(2-hy­dr­oxy­prop­yl)-4,5-di­phenyl-1H-imidazol-2-yl]benzoic acid

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4-[1-(2-hydroxypropyl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid