In the title compound, C
28H
23BrN
2OS, the dihedral angles formed by the imidazole ring with the 5-bromothiophenyl 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-phenylalaninol starting material. In the crystal, molecules are linked by O—H

N hydrogen bonds, forming chains running parallel to the
a-axis direction.
Supporting information
CCDC reference: 964035
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.085
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X H1 .. H23B .. 1.95 Ang.
Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? Do !
PLAT791_ALERT_4_G Note: The Model has Chirality at C22 (Verify) S
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 89 %
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 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
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
The starting materials, L-phenylalaninol, benzil, ammonium acetate and
5-bromothiophene-2-carbaldehyde, are commercially available. In a three-neck
round-bottomed flask fitted with a reflux condenser, L-phenylalaninol
(0.76 g, 5 mmol), molar equivalents benzil, ammonium acetate and
5-bromothiophene-2-carbaldehyde were dissolved in CH3OH (30 mL). The mixture
was kept at 65°C for 12 h. The resulting solution was cooled to
room temperature and
evaporation of the solvent gave the crude product. Crystallization of the
crude product in CH3OH afforded colourless crystals of the title compound.
The hydroxy H atom was located in a difference Fourier map and refined
freely. All other H atoms were placed geometrically and refined as riding,
with C—H = 0.93-0.98 Å, and with Uiso(H) = 1.2 Ueq(C).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 (Dolomanov et al., 2009).
2-[2-(5-Bromothiophen-2-yl)-4,5-diphenyl-1
H-imidazol-1-yl]-3-phenylpropan-1-ol
top
Crystal data top
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 |
Data collection top
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 top
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) |
Crystal data top
C28H23BrN2OS | V = 2395.97 (8) Å3 |
Mr = 515.45 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 9.36677 (18) Å | µ = 3.33 mm−1 |
b = 15.8434 (3) Å | T = 291 K |
c = 16.1452 (3) Å | 0.3 × 0.28 × 0.26 mm |
Data collection top
Agilent Xcalibur (Eos, Gemini) diffractometer | 4264 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 4033 reflections with I > 2σ(I) |
Tmin = 0.853, Tmax = 1.000 | Rint = 0.019 |
8866 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.085 | Δρmax = 0.22 e Å−3 |
S = 1.03 | Δρmin = −0.44 e Å−3 |
4264 reflections | Absolute structure: Flack (1983); 1834 Friedel pairs |
302 parameters | Absolute structure parameter: −0.004 (16) |
0 restraints | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) top
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) x+1/2, −y+3/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
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) x+1/2, −y+3/2, −z+1. |
The development of imidazoles with an heterocyclic substituent in 2-position from readily available inexpensive starting materials has been an active topic in modern organic chemistry (Jiang et al., 2009; Wu et al., 2010; Eseola et al., 2010). Our group is interested in the research of chiral imidazolium derivatives derived from natural amino acids (Mao et al., 2010; Yang et al., 2012; Xiao et al., 2012). A convenient and highly efficient one-pot-multicomponent protocol has been developed for the synthesis of the title compound from L-phenylalaninol, 5-bromothiophene-2-carbaldehyde, dibenzoyl and ammonium acetate.
The molecular structure of the title compound is shown in Figure 1. As expected, the imidazole core (C7/C8/N2/C24/N1) is essentially planar, the maximum deviation being 0.008 (3) Å for atom C24. The dihedral angle between the 5-bromothiophenyl ring and imidazole ring is 76.90 (8)°. The dihedral angles between the two phenyl substituents (C1–C6, C9–C14) and the imidazole ring are 34.02 (10)° and 80.93 (11)°, respectively. The chiral C22 carbon atom maintains the S configuration of the L-phenylalaninol starting material. In the crystal, intermolecular O—H···N hydrogen bonds (Table 1) link molecules into chains running parallel to the a axis.