2-[2-(5-Bromo-thio-phen-2-yl)-4,5-diphenyl-1H-imidazol-1-yl]-3-phenyl-propan-1-ol.

In the title compound, C28H23BrN2OS, the dihedral angles formed by the imidazole ring with the 5-bromo-thio-phenyl and phenyl rings are 76.90 (8), 34.02 (10) and 80.93 (11)°, respectively. The chiral centre maintains the S configuration of the l-phenyl-alaninol starting material. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming chains running parallel to the a-axis direction.

Related literature

For the synthesis of imidazole rings, see: Jiang et al. (2009 ▶); Wu et al. (2010 ▶); Eseola et al. (2010 ▶). For related compounds synthesized by our group, see: Mao et al. (2010 ▶); Yang et al. (2012 ▶); Xiao et al. (2012 ▶).

Experimental

Crystal data

C28H23BrN2OS

M = 515.45

Orthorhombic,

a = 9.36677 (18) Å

b = 15.8434 (3) Å

c = 16.1452 (3) Å

V = 2395.97 (8) Å3

Z = 4

Cu Kα radiation

μ = 3.33 mm−1

T = 291 K

0.3 × 0.28 × 0.26 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.853, T max = 1.000

8866 measured reflections

4264 independent reflections

4033 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.03

4264 reflections

302 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.44 e Å−3

Absolute structure: Flack (1983 ▶); 1834 Friedel pairs

Absolute structure parameter: −0.004 (16)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813021016/rz5079sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021016/rz5079Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021016/rz5079Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H23BrN2OS	F(000) = 1056
Mr = 515.45	Dx = 1.429 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4493 reflections
a = 9.36677 (18) Å	θ = 3.9–72.3°
b = 15.8434 (3) Å	µ = 3.33 mm−1
c = 16.1452 (3) Å	T = 291 K
V = 2395.97 (8) Å3	Block, colourless
Z = 4	0.3 × 0.28 × 0.26 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	4264 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4033 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 16.2312 pixels mm-1	θmax = 67.1°, θmin = 3.9°
ω scans	h = −11→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→18
Tmin = 0.853, Tmax = 1.000	l = −19→19
8866 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.2535P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4264 reflections	Δρmax = 0.22 e Å−3
302 parameters	Δρmin = −0.44 e Å−3
0 restraints	Absolute structure: Flack (1983); 1834 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.004 (16)

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.

	x	y	z	Uiso*/Ueq
Br1	0.26010 (5)	0.97884 (3)	0.26215 (3)	0.08774 (14)
S1	0.29866 (8)	0.83956 (5)	0.39570 (5)	0.06109 (18)
O1	0.5090 (3)	0.60857 (15)	0.42808 (18)	0.0755 (7)
H1	0.537 (4)	0.658 (3)	0.428 (3)	0.093 (14)*
N1	0.1628 (2)	0.73730 (13)	0.56318 (13)	0.0467 (4)
N2	0.2202 (2)	0.62572 (12)	0.48784 (12)	0.0422 (4)
C1	0.1975 (3)	0.75939 (19)	0.74105 (18)	0.0607 (6)
H1A	0.2348	0.8022	0.7082	0.073*
C2	0.1762 (4)	0.7731 (2)	0.8247 (2)	0.0731 (9)
H2	0.2011	0.8246	0.8481	0.088*
C3	0.1178 (4)	0.7098 (2)	0.87404 (18)	0.0737 (9)
H3	0.1026	0.7192	0.9302	0.088*
C4	0.0831 (4)	0.6345 (2)	0.83955 (19)	0.0667 (8)
H4	0.0435	0.5923	0.8723	0.080*
C5	0.1059 (3)	0.61977 (17)	0.75615 (17)	0.0561 (6)
H5	0.0825	0.5675	0.7337	0.067*
C6	0.1632 (3)	0.68165 (16)	0.70573 (15)	0.0464 (5)
C7	0.1817 (2)	0.67005 (15)	0.61521 (14)	0.0429 (5)
C8	0.2177 (2)	0.59945 (14)	0.57013 (14)	0.0412 (5)
C9	0.2546 (3)	0.51201 (13)	0.59565 (14)	0.0445 (5)
C10	0.3964 (3)	0.48806 (18)	0.6020 (2)	0.0628 (7)
H10	0.4682	0.5264	0.5892	0.075*
C11	0.4316 (5)	0.4072 (2)	0.6272 (3)	0.0819 (11)
H11	0.5269	0.3913	0.6313	0.098*
C12	0.3253 (5)	0.3500 (2)	0.6463 (2)	0.0811 (11)
H12	0.3488	0.2959	0.6641	0.097*
C13	0.1856 (5)	0.3734 (2)	0.6388 (2)	0.0772 (10)
H13	0.1139	0.3348	0.6512	0.093*
C14	0.1495 (3)	0.45393 (19)	0.61287 (19)	0.0601 (7)
H14	0.0539	0.4688	0.6071	0.072*
C15	0.0418 (3)	0.41288 (18)	0.4051 (2)	0.0625 (7)
H15	0.1258	0.3886	0.3856	0.075*
C16	−0.0611 (4)	0.3619 (2)	0.4394 (2)	0.0754 (9)
H16	−0.0465	0.3040	0.4427	0.091*
C17	−0.1868 (4)	0.3970 (3)	0.4690 (2)	0.0799 (10)
H17	−0.2571	0.3627	0.4919	0.096*
C18	−0.2062 (4)	0.4825 (3)	0.4643 (2)	0.0789 (9)
H18	−0.2897	0.5067	0.4845	0.095*
C19	−0.1017 (3)	0.5331 (2)	0.42947 (19)	0.0636 (7)
H19	−0.1162	0.5911	0.4267	0.076*
C20	0.0242 (3)	0.49927 (17)	0.39859 (16)	0.0512 (6)
C21	0.1378 (3)	0.55276 (18)	0.35912 (15)	0.0514 (6)
H21A	0.0956	0.6056	0.3412	0.062*
H21B	0.1737	0.5240	0.3104	0.062*
C22	0.2629 (3)	0.57177 (13)	0.41736 (14)	0.0440 (5)
H22	0.2925	0.5176	0.4410	0.053*
C23	0.3935 (3)	0.60763 (16)	0.37267 (17)	0.0515 (6)
H23A	0.4164	0.5730	0.3250	0.062*
H23B	0.3736	0.6645	0.3535	0.062*
C24	0.1849 (3)	0.70913 (15)	0.48779 (15)	0.0440 (5)
C25	0.1707 (3)	0.76397 (15)	0.41474 (15)	0.0479 (5)
C26	0.0587 (4)	0.7737 (2)	0.3627 (2)	0.0661 (8)
H26	−0.0214	0.7391	0.3639	0.079*
C27	0.0743 (4)	0.8412 (2)	0.3063 (2)	0.0672 (8)
H27	0.0069	0.8558	0.2665	0.081*
C28	0.1975 (3)	0.88144 (18)	0.31747 (17)	0.0582 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.0876 (2)	0.0822 (2)	0.0934 (3)	0.00601 (19)	0.0010 (2)	0.04352 (19)
S1	0.0579 (4)	0.0608 (4)	0.0646 (4)	−0.0061 (3)	−0.0146 (3)	0.0179 (3)
O1	0.0605 (12)	0.0598 (12)	0.1062 (19)	−0.0204 (10)	−0.0170 (12)	0.0204 (13)
N1	0.0503 (11)	0.0417 (10)	0.0482 (10)	0.0091 (9)	0.0002 (9)	−0.0031 (8)
N2	0.0445 (10)	0.0396 (9)	0.0424 (9)	0.0005 (8)	−0.0027 (8)	−0.0058 (7)
C1	0.0658 (15)	0.0574 (14)	0.0588 (15)	0.0018 (13)	0.0066 (13)	−0.0128 (13)
C2	0.082 (2)	0.0712 (19)	0.0659 (18)	0.0060 (17)	0.0016 (16)	−0.0252 (16)
C3	0.089 (2)	0.086 (2)	0.0468 (14)	0.0267 (19)	0.0031 (15)	−0.0161 (15)
C4	0.081 (2)	0.0697 (19)	0.0492 (15)	0.0164 (16)	0.0028 (15)	0.0049 (14)
C5	0.0658 (15)	0.0532 (14)	0.0493 (14)	0.0095 (12)	0.0009 (13)	−0.0003 (12)
C6	0.0430 (12)	0.0497 (13)	0.0465 (12)	0.0116 (10)	−0.0045 (10)	−0.0066 (10)
C7	0.0429 (11)	0.0438 (11)	0.0419 (11)	0.0059 (10)	0.0007 (9)	−0.0027 (10)
C8	0.0394 (12)	0.0403 (10)	0.0438 (11)	−0.0012 (9)	−0.0037 (9)	−0.0025 (9)
C9	0.0522 (12)	0.0398 (10)	0.0416 (10)	0.0021 (10)	−0.0035 (10)	−0.0058 (8)
C10	0.0583 (16)	0.0536 (15)	0.0765 (18)	0.0071 (13)	−0.0085 (15)	−0.0030 (15)
C11	0.085 (2)	0.070 (2)	0.092 (3)	0.0318 (19)	−0.016 (2)	−0.0027 (19)
C12	0.135 (3)	0.0417 (14)	0.0667 (19)	0.0170 (19)	−0.007 (2)	0.0008 (14)
C13	0.112 (3)	0.0451 (15)	0.074 (2)	−0.0154 (17)	0.003 (2)	0.0015 (14)
C14	0.0639 (17)	0.0530 (14)	0.0633 (16)	−0.0069 (13)	0.0005 (14)	−0.0037 (13)
C15	0.0645 (17)	0.0576 (16)	0.0654 (17)	−0.0092 (13)	−0.0040 (14)	−0.0081 (14)
C16	0.093 (2)	0.0605 (18)	0.073 (2)	−0.0212 (17)	−0.0041 (19)	0.0017 (15)
C17	0.075 (2)	0.099 (3)	0.0658 (19)	−0.035 (2)	−0.0058 (17)	0.0093 (18)
C18	0.0549 (17)	0.110 (3)	0.0721 (19)	−0.0020 (18)	0.0054 (14)	0.0033 (19)
C19	0.0636 (17)	0.0641 (17)	0.0633 (16)	0.0032 (14)	−0.0007 (14)	−0.0025 (14)
C20	0.0532 (14)	0.0564 (14)	0.0441 (12)	−0.0059 (11)	−0.0097 (11)	−0.0081 (11)
C21	0.0592 (15)	0.0526 (14)	0.0426 (12)	−0.0050 (12)	−0.0050 (11)	−0.0059 (11)
C22	0.0501 (12)	0.0370 (9)	0.0451 (11)	−0.0024 (10)	0.0006 (11)	−0.0057 (8)
C23	0.0566 (15)	0.0424 (12)	0.0556 (14)	−0.0028 (11)	0.0051 (12)	−0.0070 (11)
C24	0.0435 (12)	0.0419 (11)	0.0466 (12)	0.0026 (10)	−0.0036 (10)	−0.0005 (10)
C25	0.0509 (13)	0.0442 (12)	0.0486 (12)	0.0049 (10)	−0.0007 (11)	−0.0029 (10)
C26	0.0626 (17)	0.0566 (15)	0.079 (2)	−0.0013 (13)	−0.0202 (16)	0.0057 (15)
C27	0.0716 (19)	0.0643 (17)	0.0658 (18)	0.0079 (16)	−0.0233 (15)	0.0063 (15)
C28	0.0672 (17)	0.0532 (14)	0.0544 (14)	0.0103 (13)	−0.0025 (13)	0.0117 (12)

Br1—C28	1.877 (3)	C12—H12	0.9300
S1—C25	1.722 (3)	C12—C13	1.366 (6)
S1—C28	1.713 (3)	C13—H13	0.9300
O1—H1	0.83 (4)	C13—C14	1.385 (5)
O1—C23	1.404 (4)	C14—H14	0.9300
N1—C7	1.368 (3)	C15—H15	0.9300
N1—C24	1.313 (3)	C15—C16	1.374 (5)
N2—C8	1.392 (3)	C15—C20	1.383 (4)
N2—C22	1.478 (3)	C16—H16	0.9300
N2—C24	1.362 (3)	C16—C17	1.386 (6)
C1—H1A	0.9300	C17—H17	0.9300
C1—C2	1.383 (4)	C17—C18	1.370 (5)
C1—C6	1.395 (4)	C18—H18	0.9300
C2—H2	0.9300	C18—C19	1.383 (5)
C2—C3	1.392 (5)	C19—H19	0.9300
C3—H3	0.9300	C19—C20	1.388 (4)
C3—C4	1.357 (5)	C20—C21	1.502 (4)
C4—H4	0.9300	C21—H21A	0.9700
C4—C5	1.383 (4)	C21—H21B	0.9700
C5—H5	0.9300	C21—C22	1.532 (3)
C5—C6	1.382 (4)	C22—H22	0.9800
C6—C7	1.483 (3)	C22—C23	1.530 (4)
C7—C8	1.377 (3)	C23—H23A	0.9700
C8—C9	1.486 (3)	C23—H23B	0.9700
C9—C10	1.385 (4)	C24—C25	1.471 (3)
C9—C14	1.376 (4)	C25—C26	1.352 (4)
C10—H10	0.9300	C26—H26	0.9300
C10—C11	1.385 (4)	C26—C27	1.412 (4)
C11—H11	0.9300	C27—H27	0.9300
C11—C12	1.381 (6)	C27—C28	1.331 (5)
C28—S1—C25	90.92 (14)	C20—C15—H15	119.1
C23—O1—H1	105 (3)	C15—C16—H16	120.0
C24—N1—C7	106.5 (2)	C15—C16—C17	120.0 (3)
C8—N2—C22	124.47 (19)	C17—C16—H16	120.0
C24—N2—C8	106.65 (19)	C16—C17—H17	120.4
C24—N2—C22	128.8 (2)	C18—C17—C16	119.3 (3)
C2—C1—H1A	119.8	C18—C17—H17	120.4
C2—C1—C6	120.3 (3)	C17—C18—H18	119.9
C6—C1—H1A	119.8	C17—C18—C19	120.1 (3)
C1—C2—H2	119.9	C19—C18—H18	119.9
C1—C2—C3	120.2 (3)	C18—C19—H19	119.2
C3—C2—H2	119.9	C18—C19—C20	121.6 (3)
C2—C3—H3	120.2	C20—C19—H19	119.2
C4—C3—C2	119.5 (3)	C15—C20—C19	117.2 (3)
C4—C3—H3	120.2	C15—C20—C21	120.4 (3)
C3—C4—H4	119.6	C19—C20—C21	122.5 (3)
C3—C4—C5	120.7 (3)	C20—C21—H21A	109.0
C5—C4—H4	119.6	C20—C21—H21B	109.0
C4—C5—H5	119.6	C20—C21—C22	113.1 (2)
C6—C5—C4	120.9 (3)	H21A—C21—H21B	107.8
C6—C5—H5	119.6	C22—C21—H21A	109.0
C1—C6—C7	119.0 (3)	C22—C21—H21B	109.0
C5—C6—C1	118.4 (3)	N2—C22—C21	112.3 (2)
C5—C6—C7	122.5 (2)	N2—C22—H22	106.5
N1—C7—C6	119.6 (2)	N2—C22—C23	111.38 (19)
N1—C7—C8	109.9 (2)	C21—C22—H22	106.5
C8—C7—C6	130.6 (2)	C23—C22—C21	113.3 (2)
N2—C8—C9	122.65 (19)	C23—C22—H22	106.5
C7—C8—N2	105.4 (2)	O1—C23—C22	108.6 (2)
C7—C8—C9	131.9 (2)	O1—C23—H23A	110.0
C10—C9—C8	119.9 (2)	O1—C23—H23B	110.0
C14—C9—C8	120.9 (2)	C22—C23—H23A	110.0
C14—C9—C10	119.2 (3)	C22—C23—H23B	110.0
C9—C10—H10	119.9	H23A—C23—H23B	108.3
C11—C10—C9	120.2 (3)	N1—C24—N2	111.6 (2)
C11—C10—H10	119.9	N1—C24—C25	121.9 (2)
C10—C11—H11	120.0	N2—C24—C25	126.5 (2)
C12—C11—C10	120.1 (3)	C24—C25—S1	119.39 (19)
C12—C11—H11	120.0	C26—C25—S1	110.4 (2)
C11—C12—H12	120.2	C26—C25—C24	129.5 (3)
C13—C12—C11	119.5 (3)	C25—C26—H26	123.0
C13—C12—H12	120.2	C25—C26—C27	114.0 (3)
C12—C13—H13	119.6	C27—C26—H26	123.0
C12—C13—C14	120.7 (3)	C26—C27—H27	124.3
C14—C13—H13	119.6	C28—C27—C26	111.4 (3)
C9—C14—C13	120.2 (3)	C28—C27—H27	124.3
C9—C14—H14	119.9	S1—C28—Br1	119.80 (18)
C13—C14—H14	119.9	C27—C28—Br1	126.9 (2)
C16—C15—H15	119.1	C27—C28—S1	113.2 (2)
C16—C15—C20	121.9 (3)
S1—C25—C26—C27	0.6 (4)	C10—C11—C12—C13	1.0 (6)
N1—C7—C8—N2	−0.1 (3)	C11—C12—C13—C14	−0.5 (6)
N1—C7—C8—C9	177.5 (2)	C12—C13—C14—C9	−1.1 (5)
N1—C24—C25—S1	72.7 (3)	C14—C9—C10—C11	−1.5 (5)
N1—C24—C25—C26	−96.9 (4)	C15—C16—C17—C18	−0.5 (5)
N2—C8—C9—C10	79.5 (3)	C15—C20—C21—C22	−79.7 (3)
N2—C8—C9—C14	−100.2 (3)	C16—C15—C20—C19	0.9 (5)
N2—C22—C23—O1	62.7 (3)	C16—C15—C20—C21	−178.7 (3)
N2—C24—C25—S1	−107.7 (3)	C16—C17—C18—C19	0.6 (5)
N2—C24—C25—C26	82.7 (4)	C17—C18—C19—C20	0.1 (5)
C1—C2—C3—C4	0.6 (6)	C18—C19—C20—C15	−0.9 (4)
C1—C6—C7—N1	−31.8 (4)	C18—C19—C20—C21	178.8 (3)
C1—C6—C7—C8	147.7 (3)	C19—C20—C21—C22	100.6 (3)
C2—C1—C6—C5	1.0 (4)	C20—C15—C16—C17	−0.3 (5)
C2—C1—C6—C7	177.5 (3)	C20—C21—C22—N2	−66.4 (3)
C2—C3—C4—C5	0.4 (5)	C20—C21—C22—C23	166.3 (2)
C3—C4—C5—C6	−0.7 (5)	C21—C22—C23—O1	−169.6 (2)
C4—C5—C6—C1	0.0 (4)	C22—N2—C8—C7	176.0 (2)
C4—C5—C6—C7	−176.4 (3)	C22—N2—C8—C9	−1.8 (4)
C5—C6—C7—N1	144.6 (3)	C22—N2—C24—N1	−175.4 (2)
C5—C6—C7—C8	−35.8 (4)	C22—N2—C24—C25	5.0 (4)
C6—C1—C2—C3	−1.3 (5)	C24—N1—C7—C6	−179.7 (2)
C6—C7—C8—N2	−179.6 (2)	C24—N1—C7—C8	0.6 (3)
C6—C7—C8—C9	−2.1 (5)	C24—N2—C8—C7	−0.5 (3)
C7—N1—C24—N2	−1.0 (3)	C24—N2—C8—C9	−178.3 (2)
C7—N1—C24—C25	178.6 (2)	C24—N2—C22—C21	−71.2 (3)
C7—C8—C9—C10	−97.7 (3)	C24—N2—C22—C23	57.1 (3)
C7—C8—C9—C14	82.6 (3)	C24—C25—C26—C27	170.9 (3)
C8—N2—C22—C21	113.1 (2)	C25—S1—C28—Br1	176.47 (18)
C8—N2—C22—C23	−118.7 (2)	C25—S1—C28—C27	0.2 (3)
C8—N2—C24—N1	1.0 (3)	C25—C26—C27—C28	−0.4 (4)
C8—N2—C24—C25	−178.6 (2)	C26—C27—C28—Br1	−175.9 (2)
C8—C9—C10—C11	178.8 (3)	C26—C27—C28—S1	0.1 (4)
C8—C9—C14—C13	−178.2 (3)	C28—S1—C25—C24	−171.9 (2)
C9—C10—C11—C12	−0.1 (6)	C28—S1—C25—C26	−0.5 (2)
C10—C9—C14—C13	2.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.83 (4)	2.04 (4)	2.838 (3)	162 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.83 (4)	2.04 (4)	2.838 (3)	162 (4)

Symmetry code: (i) .