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organic compounds
In the crystal structure of the title compound, C17H14N2O2, the 4-phenyl ring is twisted by 24.4 (3)° and the 5-phenyl ring by 72.6 (2)° with respect to the imidazole ring. Four adjacent molecules are linked by short O—HN [ON = 2.602 (6) Å] interactions into a hydrogen-bonded tetrameric entity. The tetramers are stacked over each other along the short c axis [5.663 (3) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017696/bt6492sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017696/bt6492Isup2.hkl |
CCDC reference: 248836
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.075
- wR factor = 0.244
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 134.00 A 3
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.800 0.979 Tmin' and Tmax expected: 0.965 0.979 RR' = 0.829 Please check that your absorption correction is appropriate. DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.720 Test value = 0.600 DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.72 e/A 3 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 1903 Count of symmetry unique reflns 1912 Completeness (_total/calc) 99.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
4,5-Diphenyl-1H-imidazole-1-acetic acid top
Crystal data top
C17H14N2O2 | Dx = 1.229 Mg m−3 |
Mr = 278.30 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I4 | Cell parameters from 13806 reflections |
Hall symbol: I -4 | θ = 3.5–27.5° |
a = 23.048 (7) Å | µ = 0.08 mm−1 |
c = 5.663 (3) Å | T = 295 K |
V = 3008 (2) Å3 | Block, colorless |
Z = 8 | 0.42 × 0.31 × 0.26 mm |
F(000) = 1168 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1903 independent reflections |
Radiation source: fine-focus sealed tube | 1659 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 3.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −29→29 |
Tmin = 0.800, Tmax = 0.979 | k = −29→29 |
14058 measured reflections | l = −7→6 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.244 | H-atom parameters constrained |
S = 1.25 | w = 1/[σ2(Fo2) + (0.1675P)2 + 0.0654P] where P = (Fo2 + 2Fc2)/3 |
1903 reflections | (Δ/σ)max = 0.001 |
191 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.5955 (2) | 0.1760 (2) | −0.0317 (9) | 0.077 (1) | |
O2 | 0.6123 (2) | 0.1178 (2) | 0.270 (1) | 0.097 (2) | |
N1 | 0.6986 (2) | 0.0613 (1) | 0.0415 (8) | 0.050 (1) | |
N2 | 0.7181 (2) | −0.0121 (2) | 0.2737 (9) | 0.056 (1) | |
C1 | 0.6205 (2) | 0.1333 (2) | 0.072 (1) | 0.057 (1) | |
C2 | 0.6624 (2) | 0.1015 (2) | −0.095 (1) | 0.057 (1) | |
C3 | 0.6823 (2) | 0.0086 (2) | 0.115 (1) | 0.059 (1) | |
C4 | 0.7604 (2) | 0.0302 (2) | 0.3097 (9) | 0.043 (1) | |
C5 | 0.7479 (2) | 0.0766 (2) | 0.1669 (8) | 0.042 (1) | |
C6 | 0.7773 (2) | 0.1333 (2) | 0.1310 (8) | 0.039 (1) | |
C7 | 0.8091 (2) | 0.1440 (2) | −0.0741 (9) | 0.047 (1) | |
C8 | 0.8384 (2) | 0.1961 (2) | −0.100 (1) | 0.053 (1) | |
C9 | 0.8361 (2) | 0.2375 (2) | 0.077 (1) | 0.053 (1) | |
C10 | 0.8043 (2) | 0.2279 (2) | 0.276 (1) | 0.055 (1) | |
C11 | 0.7742 (2) | 0.1757 (2) | 0.3045 (9) | 0.049 (1) | |
C12 | 0.8084 (2) | 0.0221 (2) | 0.4779 (8) | 0.041 (1) | |
C13 | 0.8606 (2) | 0.0526 (2) | 0.4535 (8) | 0.044 (1) | |
C14 | 0.9041 (2) | 0.0475 (2) | 0.622 (1) | 0.050 (1) | |
C15 | 0.8971 (2) | 0.0111 (2) | 0.813 (1) | 0.055 (1) | |
C16 | 0.8467 (2) | −0.0211 (2) | 0.836 (1) | 0.057 (1) | |
C17 | 0.8029 (2) | −0.0156 (2) | 0.671 (1) | 0.051 (1) | |
H1 | 0.5663 | 0.1852 | 0.0420 | 0.093* | |
H2a | 0.6405 | 0.0802 | −0.2126 | 0.068* | |
H2b | 0.6868 | 0.1294 | −0.1757 | 0.068* | |
H3 | 0.6497 | −0.0109 | 0.0597 | 0.070* | |
H7 | 0.8107 | 0.1163 | −0.1932 | 0.056* | |
H8 | 0.8598 | 0.2032 | −0.2360 | 0.064* | |
H9 | 0.8563 | 0.2722 | 0.0593 | 0.064* | |
H10 | 0.8026 | 0.2561 | 0.3931 | 0.066* | |
H11 | 0.7522 | 0.1694 | 0.4396 | 0.059* | |
H13 | 0.8662 | 0.0764 | 0.3230 | 0.052* | |
H14 | 0.9381 | 0.0689 | 0.6064 | 0.060* | |
H15 | 0.9262 | 0.0081 | 0.9256 | 0.066* | |
H16 | 0.8424 | −0.0465 | 0.9619 | 0.068* | |
H17 | 0.7692 | −0.0372 | 0.6886 | 0.061* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.058 (2) | 0.073 (2) | 0.101 (3) | 0.025 (2) | 0.024 (2) | 0.040 (2) |
O2 | 0.104 (3) | 0.098 (3) | 0.088 (3) | 0.047 (3) | 0.025 (3) | 0.029 (3) |
N1 | 0.045 (2) | 0.039 (2) | 0.068 (3) | 0.005 (1) | −0.007 (2) | 0.001 (2) |
N2 | 0.049 (2) | 0.038 (2) | 0.080 (3) | −0.004 (1) | −0.008 (2) | 0.005 (2) |
C1 | 0.042 (2) | 0.046 (2) | 0.082 (4) | 0.004 (2) | 0.003 (2) | 0.016 (3) |
C2 | 0.048 (2) | 0.052 (2) | 0.069 (3) | 0.008 (2) | −0.005 (2) | 0.013 (2) |
C3 | 0.052 (2) | 0.044 (2) | 0.080 (4) | −0.007 (2) | −0.012 (3) | 0.003 (2) |
C4 | 0.042 (2) | 0.032 (2) | 0.054 (2) | 0.002 (1) | 0.001 (2) | 0.000 (2) |
C5 | 0.039 (2) | 0.036 (2) | 0.051 (2) | 0.007 (1) | 0.004 (2) | −0.006 (2) |
C6 | 0.040 (2) | 0.031 (2) | 0.044 (2) | 0.007 (1) | 0.002 (2) | 0.002 (2) |
C7 | 0.052 (2) | 0.044 (2) | 0.043 (2) | 0.006 (2) | 0.006 (2) | −0.005 (2) |
C8 | 0.051 (2) | 0.056 (2) | 0.052 (2) | 0.000 (2) | 0.003 (2) | 0.013 (2) |
C9 | 0.052 (2) | 0.042 (2) | 0.065 (3) | −0.006 (2) | −0.012 (2) | 0.008 (2) |
C10 | 0.073 (3) | 0.039 (2) | 0.053 (3) | 0.001 (2) | −0.005 (2) | −0.005 (2) |
C11 | 0.064 (2) | 0.039 (2) | 0.044 (2) | 0.005 (2) | 0.007 (2) | −0.003 (2) |
C12 | 0.046 (2) | 0.030 (2) | 0.046 (2) | 0.002 (1) | 0.003 (2) | −0.003 (2) |
C13 | 0.043 (2) | 0.042 (2) | 0.046 (2) | 0.003 (2) | 0.008 (2) | 0.002 (2) |
C14 | 0.043 (2) | 0.047 (2) | 0.059 (3) | 0.000 (2) | 0.002 (2) | −0.005 (2) |
C15 | 0.060 (3) | 0.053 (2) | 0.052 (2) | 0.007 (2) | −0.009 (2) | −0.002 (2) |
C16 | 0.073 (3) | 0.046 (2) | 0.052 (3) | −0.001 (2) | −0.002 (2) | 0.010 (2) |
C17 | 0.054 (2) | 0.041 (2) | 0.058 (3) | −0.008 (2) | 0.001 (2) | 0.003 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.285 (6) | C13—C14 | 1.390 (7) |
O2—C1 | 1.192 (8) | C14—C15 | 1.375 (7) |
N1—C3 | 1.337 (6) | C15—C16 | 1.384 (7) |
N1—C5 | 1.384 (6) | C16—C17 | 1.379 (7) |
N1—C2 | 1.466 (6) | O1—H1 | 0.82 |
N2—C3 | 1.311 (7) | C2—H2a | 0.97 |
N2—C4 | 1.394 (5) | C2—H2b | 0.97 |
C1—C2 | 1.538 (8) | C3—H3 | 0.93 |
C4—C5 | 1.371 (6) | C7—H7 | 0.93 |
C4—C12 | 1.473 (6) | C8—H8 | 0.93 |
C5—C6 | 1.486 (5) | C9—H9 | 0.93 |
C6—C11 | 1.387 (6) | C10—H10 | 0.93 |
C6—C7 | 1.397 (6) | C11—H11 | 0.93 |
C7—C8 | 1.384 (6) | C13—H13 | 0.93 |
C8—C9 | 1.384 (7) | C14—H14 | 0.93 |
C9—C10 | 1.364 (8) | C15—H15 | 0.93 |
C10—C11 | 1.399 (6) | C16—H16 | 0.93 |
C12—C13 | 1.398 (5) | C17—H17 | 0.93 |
C12—C17 | 1.403 (6) | ||
C2—N1—C3 | 125.2 (4) | C12—C17—C16 | 121.2 (4) |
C2—N1—C5 | 125.2 (3) | C1—O1—H1 | 109.5 |
C3—N1—C5 | 107.6 (4) | N1—C2—H2a | 109.8 |
C3—N2—C4 | 106.5 (4) | C1—C2—H2a | 109.8 |
O1—C1—O2 | 126.2 (6) | N1—C2—H2b | 109.8 |
O1—C1—C2 | 111.4 (5) | C1—C2—H2b | 109.8 |
O2—C1—C2 | 122.4 (5) | H2a—C2—H2b | 108.2 |
N1—C2—C1 | 109.5 (5) | N2—C3—H3 | 124.2 |
N1—C3—N2 | 111.6 (4) | N1—C3—H3 | 124.2 |
N2—C4—C5 | 108.2 (4) | C8—C7—H7 | 120.1 |
N2—C4—C12 | 122.2 (4) | C6—C7—H7 | 120.1 |
C5—C4—C12 | 129.7 (3) | C9—C8—H8 | 119.9 |
N1—C5—C4 | 106.1 (3) | C7—C8—H8 | 119.9 |
N1—C5—C6 | 121.8 (4) | C10—C9—H9 | 119.8 |
C4—C5—C6 | 132.1 (4) | C8—C9—H9 | 119.8 |
C5—C6—C11 | 120.0 (4) | C9—C10—H10 | 119.9 |
C7—C6—C11 | 119.4 (4) | C11—C10—H10 | 119.9 |
C5—C6—C7 | 120.6 (4) | C6—C11—H11 | 120.0 |
C6—C7—C8 | 119.8 (4) | C10—C11—H11 | 120.0 |
C7—C8—C9 | 120.3 (5) | C14—C13—H13 | 119.7 |
C8—C9—C10 | 120.4 (4) | C12—C13—H13 | 119.7 |
C9—C10—C11 | 120.1 (4) | C15—C14—H14 | 119.8 |
C6—C11—C10 | 119.9 (4) | C13—C14—H14 | 119.8 |
C13—C12—C17 | 117.7 (4) | C14—C15—H15 | 120.0 |
C4—C12—C13 | 121.3 (4) | C16—C15—H15 | 120.0 |
C4—C12—C17 | 121.0 (4) | C17—C16—H16 | 120.0 |
C12—C13—C14 | 120.7 (4) | C15—C16—H16 | 120.0 |
C13—C14—C15 | 120.3 (4) | C16—C17—H17 | 119.4 |
C14—C15—C16 | 120.0 (5) | C12—C17—H17 | 119.4 |
C15—C16—C17 | 120.0 (5) | ||
C3—N1—C2—C1 | 80.5 (6) | C11—C6—C7—C8 | 1.6 (6) |
C5—N1—C2—C1 | −81.4 (6) | C5—C6—C7—C8 | −177.0 (4) |
O2—C1—C2—N1 | −13.6 (7) | C6—C7—C8—C9 | −0.2 (7) |
O1—C1—C2—N1 | 168.3 (4) | C7—C8—C9—C10 | −0.9 (7) |
C4—N2—C3—N1 | 0.8 (6) | C8—C9—C10—C11 | 0.7 (7) |
C5—N1—C3—N2 | −1.6 (6) | C7—C6—C11—C10 | −1.9 (6) |
C2—N1—C3—N2 | −166.2 (5) | C5—C6—C11—C10 | 176.8 (4) |
C3—N2—C4—C5 | 0.4 (6) | C9—C10—C11—C6 | 0.7 (7) |
C3—N2—C4—C12 | −180.0 (4) | C5—C4—C12—C13 | −24.3 (7) |
N2—C4—C5—N1 | −1.3 (5) | N2—C4—C12—C13 | 156.0 (4) |
C12—C4—C5—N1 | 179.0 (4) | C5—C4—C12—C17 | 154.4 (5) |
N2—C4—C5—C6 | 179.9 (4) | N2—C4—C12—C17 | −25.2 (6) |
C12—C4—C5—C6 | 0.2 (8) | C17—C12—C13—C14 | −3.2 (6) |
C3—N1—C5—C4 | 1.8 (5) | C4—C12—C13—C14 | 175.6 (4) |
C2—N1—C5—C4 | 166.3 (5) | C12—C13—C14—C15 | 1.9 (6) |
C3—N1—C5—C6 | −179.3 (4) | C13—C14—C15—C16 | 0.6 (7) |
C2—N1—C5—C6 | −14.7 (7) | C14—C15—C16—C17 | −1.7 (8) |
C4—C5—C6—C11 | −72.5 (6) | C15—C16—C17—C12 | 0.4 (7) |
N1—C5—C6—C11 | 108.8 (5) | C13—C12—C17—C16 | 2.0 (6) |
C4—C5—C6—C7 | 106.0 (6) | C4—C12—C17—C16 | −176.8 (4) |
N1—C5—C6—C7 | −72.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.82 | 1.79 | 2.602 (6) | 168 |
Symmetry code: (i) −y+1/2, x−1/2, −z+1/2. |
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