4-Chloro-2-[1-(4-ethyl­phen­yl)-4,5-diphenyl-1H-imidazol-2-yl]phenol

In the title compound, C₂₉H₂₃ClN₂O, the 5-chloro­phenol ring and the imidazole ring are nearly coplanar, with a dihedral angle of 15.76 (9)° between them. The ethyl­phenyl ring and the two phenyl rings subtend angles of 71.09 (7), 43.95 (5) and 36.53 (9)°, respectively, with the imidazole plane. An intra­molecular O—H...N hydrogen bond supports the mol­ecular conformation, and an inter­molecular C—H...O inter­action, originating from an ortho-phenyl H atom, stabilizes the packing arrangement. In addition, a weak C—H...π inter­action, also involving an ortho-phenyl H atom, is observed.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.129
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.180 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         22 Report

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   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
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015).

4-Chloro-2-[1-(4-ethylphenyl)-4,5-diphenyl-1H-imidazol-2-yl]phenol

Crystal data

C29H23ClN2O	F(000) = 944
Mr = 450.94	Dx = 1.277 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0627 (6) Å	Cell parameters from 4807 reflections
b = 10.7595 (8) Å	θ = 2.6–26.5°
c = 24.4636 (19) Å	µ = 0.19 mm^−1
β = 100.599 (3)°	T = 297 K
V = 2344.7 (3) Å^3	Block, colorless
Z = 4	0.45 × 0.38 × 0.35 mm

Data collection

Bruker SMART APEX CCD diffractometer	3593 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
ω scans	θmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
Tmin = 0.821, Tmax = 0.928	k = −13→13
34596 measured reflections	l = −30→30
4807 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0461P)^2 + 1.5828P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4807 reflections	Δρmax = 0.26 e Å^−3
301 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0135 (11)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. H atoms were placed at calculated positions in the riding-model approximation, with O—H = 1.00 Å and C—H = 0.93, 0.96 and 0.97 Å for aromatic, methyl and methine H atoms, respectively, and with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) otherwise.

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

	x	y	z	Uiso*/Ueq
Cl1	1.10374 (7)	0.46682 (6)	1.17331 (2)	0.0588 (2)
O1	0.67555 (18)	0.23218 (14)	0.99506 (7)	0.0538 (4)
H1	0.647 (3)	0.2890 (19)	0.9625 (11)	0.081*
N1	0.65078 (19)	0.43455 (15)	0.93998 (7)	0.0412 (4)
N2	0.71390 (18)	0.61739 (15)	0.97832 (6)	0.0367 (4)
C1	0.7255 (2)	0.49090 (18)	0.98494 (8)	0.0374 (4)
C2	0.6291 (2)	0.64067 (18)	0.92560 (7)	0.0365 (4)
C3	0.5904 (2)	0.52542 (18)	0.90324 (8)	0.0372 (4)
C4	0.8032 (2)	0.42008 (18)	1.03298 (8)	0.0369 (4)
C5	0.7687 (2)	0.29210 (19)	1.03599 (8)	0.0404 (5)
C6	0.8346 (2)	0.2226 (2)	1.08197 (9)	0.0451 (5)
H6	0.808858	0.139367	1.084268	0.054*
C7	0.9371 (2)	0.2747 (2)	1.12404 (8)	0.0453 (5)
H7	0.980055	0.227497	1.154686	0.054*
C8	0.9756 (2)	0.3984 (2)	1.12027 (8)	0.0407 (5)
C9	0.9117 (2)	0.47049 (19)	1.07553 (8)	0.0401 (4)
H9	0.940636	0.553051	1.073556	0.048*
C10	0.7779 (2)	0.70811 (17)	1.01924 (7)	0.0343 (4)
C11	0.7207 (2)	0.7207 (2)	1.06745 (8)	0.0410 (5)
H11	0.634020	0.678509	1.071702	0.049*
C12	0.7936 (2)	0.7967 (2)	1.10933 (8)	0.0465 (5)
H12	0.755755	0.804476	1.142025	0.056*
C13	0.9217 (2)	0.86161 (19)	1.10368 (8)	0.0431 (5)
C14	0.9724 (2)	0.8518 (2)	1.05376 (9)	0.0483 (5)
H14	1.055933	0.897377	1.048605	0.058*
C15	0.9012 (2)	0.7755 (2)	1.01134 (8)	0.0428 (5)
H15	0.936377	0.769909	0.978027	0.051*
C16	1.0063 (3)	0.9367 (2)	1.15138 (10)	0.0616 (7)
H16A	0.936247	0.989876	1.165958	0.074*
H16B	1.078251	0.989614	1.137768	0.074*
C17	1.0880 (4)	0.8561 (3)	1.19769 (13)	0.0940 (11)
H17A	1.139962	0.907784	1.227008	0.141*
H17B	1.017021	0.804672	1.211867	0.141*
H17C	1.159005	0.804410	1.183681	0.141*
C18	0.6046 (2)	0.76627 (18)	0.90155 (8)	0.0372 (4)
C19	0.5629 (3)	0.8667 (2)	0.93102 (9)	0.0504 (5)
H19	0.549954	0.855868	0.967564	0.061*
C20	0.5404 (3)	0.9826 (2)	0.90656 (11)	0.0641 (7)
H20	0.513916	1.049426	0.926859	0.077*
C21	0.5569 (3)	0.9994 (2)	0.85245 (12)	0.0686 (8)
H21	0.540690	1.077261	0.835939	0.082*
C22	0.5975 (3)	0.9009 (2)	0.82270 (10)	0.0639 (7)
H22	0.608119	0.912305	0.785941	0.077*
C23	0.6226 (2)	0.7851 (2)	0.84696 (9)	0.0475 (5)
H23	0.651751	0.719374	0.826657	0.057*
C24	0.4960 (2)	0.48681 (18)	0.85017 (8)	0.0376 (4)
C25	0.3671 (2)	0.5502 (2)	0.82669 (9)	0.0490 (5)
H25	0.341256	0.623145	0.843045	0.059*
C26	0.2763 (3)	0.5057 (3)	0.77900 (10)	0.0602 (6)
H26	0.190035	0.549194	0.763527	0.072*
C27	0.3123 (3)	0.3978 (3)	0.75417 (9)	0.0599 (6)
H27	0.250298	0.368055	0.722302	0.072*
C28	0.4405 (3)	0.3347 (2)	0.77687 (9)	0.0568 (6)
H28	0.466097	0.262341	0.760037	0.068*
C29	0.5316 (3)	0.3779 (2)	0.82458 (8)	0.0471 (5)
H29	0.617670	0.333929	0.839817	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0561 (3)	0.0675 (4)	0.0446 (3)	0.0094 (3)	−0.0121 (2)	−0.0065 (3)
O1	0.0686 (10)	0.0383 (8)	0.0474 (9)	−0.0101 (7)	−0.0079 (7)	0.0039 (7)
N1	0.0487 (10)	0.0358 (9)	0.0348 (8)	−0.0001 (7)	−0.0034 (7)	0.0022 (7)
N2	0.0440 (9)	0.0315 (8)	0.0318 (8)	−0.0011 (7)	−0.0006 (7)	0.0009 (6)
C1	0.0424 (10)	0.0343 (10)	0.0326 (9)	0.0000 (8)	−0.0008 (8)	0.0025 (8)
C2	0.0400 (10)	0.0363 (10)	0.0311 (9)	0.0031 (8)	0.0011 (8)	0.0010 (8)
C3	0.0414 (10)	0.0362 (10)	0.0316 (9)	0.0025 (8)	0.0006 (8)	0.0026 (8)
C4	0.0421 (10)	0.0335 (10)	0.0336 (9)	0.0027 (8)	0.0027 (8)	0.0030 (8)
C5	0.0450 (11)	0.0380 (10)	0.0372 (10)	0.0005 (9)	0.0043 (8)	0.0021 (8)
C6	0.0543 (12)	0.0377 (11)	0.0433 (11)	0.0023 (9)	0.0086 (9)	0.0089 (9)
C7	0.0515 (12)	0.0488 (12)	0.0347 (10)	0.0112 (10)	0.0051 (9)	0.0110 (9)
C8	0.0416 (10)	0.0466 (12)	0.0320 (10)	0.0096 (9)	0.0020 (8)	−0.0016 (9)
C9	0.0441 (11)	0.0364 (10)	0.0370 (10)	0.0052 (8)	−0.0001 (8)	0.0020 (8)
C10	0.0372 (9)	0.0331 (9)	0.0304 (9)	0.0013 (8)	0.0004 (7)	−0.0011 (7)
C11	0.0377 (10)	0.0483 (12)	0.0373 (10)	−0.0013 (9)	0.0076 (8)	0.0021 (9)
C12	0.0518 (12)	0.0558 (13)	0.0321 (10)	0.0068 (10)	0.0083 (9)	−0.0040 (9)
C13	0.0497 (12)	0.0388 (11)	0.0368 (10)	0.0045 (9)	−0.0024 (9)	−0.0023 (9)
C14	0.0479 (12)	0.0486 (12)	0.0478 (12)	−0.0126 (10)	0.0073 (9)	−0.0018 (10)
C15	0.0477 (11)	0.0466 (12)	0.0355 (10)	−0.0050 (9)	0.0109 (9)	−0.0023 (9)
C16	0.0747 (16)	0.0534 (14)	0.0492 (13)	−0.0026 (12)	−0.0083 (12)	−0.0121 (11)
C17	0.113 (3)	0.083 (2)	0.0662 (18)	−0.0077 (19)	−0.0367 (17)	0.0015 (16)
C18	0.0393 (10)	0.0357 (10)	0.0337 (9)	0.0006 (8)	−0.0007 (8)	0.0013 (8)
C19	0.0603 (14)	0.0431 (12)	0.0457 (12)	0.0093 (10)	0.0038 (10)	−0.0019 (10)
C20	0.0767 (17)	0.0389 (12)	0.0701 (17)	0.0139 (12)	−0.0044 (13)	−0.0034 (12)
C21	0.0850 (19)	0.0389 (13)	0.0733 (18)	0.0027 (12)	−0.0085 (14)	0.0181 (12)
C22	0.0799 (17)	0.0586 (15)	0.0495 (14)	−0.0013 (13)	0.0021 (12)	0.0194 (12)
C23	0.0583 (13)	0.0450 (12)	0.0377 (11)	0.0030 (10)	0.0047 (9)	0.0056 (9)
C24	0.0414 (10)	0.0391 (10)	0.0307 (9)	−0.0038 (8)	0.0025 (8)	0.0006 (8)
C25	0.0476 (12)	0.0532 (13)	0.0431 (11)	0.0037 (10)	0.0000 (9)	−0.0028 (10)
C26	0.0478 (13)	0.0774 (18)	0.0484 (13)	0.0038 (12)	−0.0092 (10)	−0.0020 (12)
C27	0.0625 (15)	0.0707 (17)	0.0408 (12)	−0.0156 (13)	−0.0060 (11)	−0.0064 (12)
C28	0.0792 (17)	0.0480 (13)	0.0403 (12)	−0.0074 (12)	0.0030 (11)	−0.0107 (10)
C29	0.0577 (13)	0.0409 (11)	0.0391 (11)	0.0029 (10)	−0.0009 (9)	−0.0013 (9)

Geometric parameters (Å, º)

Cl1—C8	1.738 (2)	C14—H14	0.9300
O1—C5	1.349 (2)	C15—H15	0.9300
O1—H1	1.00 (3)	C16—C17	1.509 (4)
N1—C1	1.327 (2)	C16—H16A	0.9700
N1—C3	1.372 (2)	C16—H16B	0.9700
N2—C1	1.372 (2)	C17—H17A	0.9600
N2—C2	1.397 (2)	C17—H17B	0.9600
N2—C10	1.441 (2)	C17—H17C	0.9600
C1—C4	1.468 (3)	C18—C23	1.390 (3)
C2—C3	1.375 (3)	C18—C19	1.390 (3)
C2—C18	1.474 (3)	C19—C20	1.382 (3)
C3—C24	1.477 (3)	C19—H19	0.9300
C4—C9	1.403 (3)	C20—C21	1.371 (4)
C4—C5	1.417 (3)	C20—H20	0.9300
C5—C6	1.391 (3)	C21—C22	1.373 (4)
C6—C7	1.373 (3)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.381 (3)
C7—C8	1.383 (3)	C22—H22	0.9300
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.379 (3)	C24—C25	1.383 (3)
C9—H9	0.9300	C24—C29	1.394 (3)
C10—C15	1.376 (3)	C25—C26	1.383 (3)
C10—C11	1.379 (3)	C25—H25	0.9300
C11—C12	1.380 (3)	C26—C27	1.377 (4)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.384 (3)	C27—C28	1.372 (4)
C12—H12	0.9300	C27—H27	0.9300
C13—C14	1.386 (3)	C28—C29	1.381 (3)
C13—C16	1.507 (3)	C28—H28	0.9300
C14—C15	1.386 (3)	C29—H29	0.9300
C5—O1—H1	109.5	C14—C15—H15	120.5
C1—N1—C3	107.38 (16)	C13—C16—C17	112.5 (2)
C1—N2—C2	107.68 (15)	C13—C16—H16A	109.1
C1—N2—C10	125.28 (15)	C17—C16—H16A	109.1
C2—N2—C10	127.04 (16)	C13—C16—H16B	109.1
N1—C1—N2	109.82 (16)	C17—C16—H16B	109.1
N1—C1—C4	121.54 (17)	H16A—C16—H16B	107.8
N2—C1—C4	128.64 (17)	C16—C17—H17A	109.5
C3—C2—N2	105.22 (16)	C16—C17—H17B	109.5
C3—C2—C18	131.25 (17)	H17A—C17—H17B	109.5
N2—C2—C18	123.34 (17)	C16—C17—H17C	109.5
N1—C3—C2	109.88 (16)	H17A—C17—H17C	109.5
N1—C3—C24	118.18 (17)	H17B—C17—H17C	109.5
C2—C3—C24	131.90 (18)	C23—C18—C19	118.45 (19)
C9—C4—C5	117.94 (17)	C23—C18—C2	118.78 (18)
C9—C4—C1	124.14 (17)	C19—C18—C2	122.77 (18)
C5—C4—C1	117.91 (17)	C20—C19—C18	120.6 (2)
O1—C5—C6	117.42 (18)	C20—C19—H19	119.7
O1—C5—C4	122.68 (17)	C18—C19—H19	119.7
C6—C5—C4	119.88 (19)	C21—C20—C19	120.2 (2)
C7—C6—C5	121.2 (2)	C21—C20—H20	119.9
C7—C6—H6	119.4	C19—C20—H20	119.9
C5—C6—H6	119.4	C20—C21—C22	119.8 (2)
C6—C7—C8	119.18 (18)	C20—C21—H21	120.1
C6—C7—H7	120.4	C22—C21—H21	120.1
C8—C7—H7	120.4	C21—C22—C23	120.5 (2)
C9—C8—C7	121.29 (19)	C21—C22—H22	119.8
C9—C8—Cl1	118.69 (17)	C23—C22—H22	119.8
C7—C8—Cl1	120.00 (15)	C22—C23—C18	120.4 (2)
C8—C9—C4	120.42 (19)	C22—C23—H23	119.8
C8—C9—H9	119.8	C18—C23—H23	119.8
C4—C9—H9	119.8	C25—C24—C29	118.41 (19)
C15—C10—C11	120.72 (18)	C25—C24—C3	122.32 (19)
C15—C10—N2	119.52 (17)	C29—C24—C3	119.12 (18)
C11—C10—N2	119.63 (17)	C26—C25—C24	120.3 (2)
C10—C11—C12	119.32 (19)	C26—C25—H25	119.8
C10—C11—H11	120.3	C24—C25—H25	119.8
C12—C11—H11	120.3	C27—C26—C25	120.8 (2)
C11—C12—C13	121.36 (19)	C27—C26—H26	119.6
C11—C12—H12	119.3	C25—C26—H26	119.6
C13—C12—H12	119.3	C28—C27—C26	119.4 (2)
C12—C13—C14	118.03 (19)	C28—C27—H27	120.3
C12—C13—C16	120.6 (2)	C26—C27—H27	120.3
C14—C13—C16	121.3 (2)	C27—C28—C29	120.4 (2)
C13—C14—C15	121.4 (2)	C27—C28—H28	119.8
C13—C14—H14	119.3	C29—C28—H28	119.8
C15—C14—H14	119.3	C28—C29—C24	120.7 (2)
C10—C15—C14	119.03 (19)	C28—C29—H29	119.6
C10—C15—H15	120.5	C24—C29—H29	119.6
C3—N1—C1—N2	0.4 (2)	C15—C10—C11—C12	−3.6 (3)
C3—N1—C1—C4	179.45 (17)	N2—C10—C11—C12	172.22 (18)
C2—N2—C1—N1	−1.1 (2)	C10—C11—C12—C13	0.8 (3)
C10—N2—C1—N1	178.44 (17)	C11—C12—C13—C14	2.3 (3)
C2—N2—C1—C4	179.94 (19)	C11—C12—C13—C16	−175.5 (2)
C10—N2—C1—C4	−0.5 (3)	C12—C13—C14—C15	−2.6 (3)
C1—N2—C2—C3	1.3 (2)	C16—C13—C14—C15	175.1 (2)
C10—N2—C2—C3	−178.22 (17)	C11—C10—C15—C14	3.3 (3)
C1—N2—C2—C18	−174.15 (18)	N2—C10—C15—C14	−172.56 (18)
C10—N2—C2—C18	6.3 (3)	C13—C14—C15—C10	−0.1 (3)
C1—N1—C3—C2	0.4 (2)	C12—C13—C16—C17	71.3 (3)
C1—N1—C3—C24	−177.67 (17)	C14—C13—C16—C17	−106.4 (3)
N2—C2—C3—N1	−1.1 (2)	C3—C2—C18—C23	−40.4 (3)
C18—C2—C3—N1	173.9 (2)	N2—C2—C18—C23	133.8 (2)
N2—C2—C3—C24	176.7 (2)	C3—C2—C18—C19	139.0 (2)
C18—C2—C3—C24	−8.4 (4)	N2—C2—C18—C19	−46.8 (3)
N1—C1—C4—C9	164.28 (19)	C23—C18—C19—C20	−0.2 (3)
N2—C1—C4—C9	−16.9 (3)	C2—C18—C19—C20	−179.6 (2)
N1—C1—C4—C5	−14.4 (3)	C18—C19—C20—C21	1.0 (4)
N2—C1—C4—C5	164.4 (2)	C19—C20—C21—C22	−0.7 (4)
C9—C4—C5—O1	−174.41 (19)	C20—C21—C22—C23	−0.4 (4)
C1—C4—C5—O1	4.4 (3)	C21—C22—C23—C18	1.1 (4)
C9—C4—C5—C6	4.1 (3)	C19—C18—C23—C22	−0.8 (3)
C1—C4—C5—C6	−177.12 (19)	C2—C18—C23—C22	178.6 (2)
O1—C5—C6—C7	176.40 (19)	N1—C3—C24—C25	140.6 (2)
C4—C5—C6—C7	−2.2 (3)	C2—C3—C24—C25	−37.0 (3)
C5—C6—C7—C8	−0.3 (3)	N1—C3—C24—C29	−34.8 (3)
C6—C7—C8—C9	0.9 (3)	C2—C3—C24—C29	147.5 (2)
C6—C7—C8—Cl1	179.40 (16)	C29—C24—C25—C26	0.1 (3)
C7—C8—C9—C4	1.1 (3)	C3—C24—C25—C26	−175.4 (2)
Cl1—C8—C9—C4	−177.38 (15)	C24—C25—C26—C27	0.1 (4)
C5—C4—C9—C8	−3.6 (3)	C25—C26—C27—C28	−0.6 (4)
C1—C4—C9—C8	177.71 (19)	C26—C27—C28—C29	0.8 (4)
C1—N2—C10—C15	107.0 (2)	C27—C28—C29—C24	−0.6 (4)
C2—N2—C10—C15	−73.5 (3)	C25—C24—C29—C28	0.1 (3)
C1—N2—C10—C11	−68.8 (3)	C3—C24—C29—C28	175.8 (2)
C2—N2—C10—C11	110.7 (2)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C4–C9 aryl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.00	1.66	2.549 (1)	145
C19—H19···O1^i	0.93	2.57	3.242 (3)	129
C15—H15···Cg^ii	0.93	2.72	3.527 (2)	146

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