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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—H...N [O...N = 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017696/bt6492sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017696/bt6492Isup2.hkl
Contains datablock I

CCDC reference: 248836

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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
C17H14N2O2Dx = 1.229 Mg m3
Mr = 278.30Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4Cell parameters from 13806 reflections
Hall symbol: I -4θ = 3.5–27.5°
a = 23.048 (7) ŵ = 0.08 mm1
c = 5.663 (3) ÅT = 295 K
V = 3008 (2) Å3Block, colorless
Z = 80.42 × 0.31 × 0.26 mm
F(000) = 1168
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1903 independent reflections
Radiation source: fine-focus sealed tube1659 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2929
Tmin = 0.800, Tmax = 0.979k = 2929
14058 measured reflectionsl = 76
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.244H-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 parametersΔρmax = 0.72 e Å3
0 restraintsΔρmin = 0.36 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5955 (2)0.1760 (2)0.0317 (9)0.077 (1)
O20.6123 (2)0.1178 (2)0.270 (1)0.097 (2)
N10.6986 (2)0.0613 (1)0.0415 (8)0.050 (1)
N20.7181 (2)0.0121 (2)0.2737 (9)0.056 (1)
C10.6205 (2)0.1333 (2)0.072 (1)0.057 (1)
C20.6624 (2)0.1015 (2)0.095 (1)0.057 (1)
C30.6823 (2)0.0086 (2)0.115 (1)0.059 (1)
C40.7604 (2)0.0302 (2)0.3097 (9)0.043 (1)
C50.7479 (2)0.0766 (2)0.1669 (8)0.042 (1)
C60.7773 (2)0.1333 (2)0.1310 (8)0.039 (1)
C70.8091 (2)0.1440 (2)0.0741 (9)0.047 (1)
C80.8384 (2)0.1961 (2)0.100 (1)0.053 (1)
C90.8361 (2)0.2375 (2)0.077 (1)0.053 (1)
C100.8043 (2)0.2279 (2)0.276 (1)0.055 (1)
C110.7742 (2)0.1757 (2)0.3045 (9)0.049 (1)
C120.8084 (2)0.0221 (2)0.4779 (8)0.041 (1)
C130.8606 (2)0.0526 (2)0.4535 (8)0.044 (1)
C140.9041 (2)0.0475 (2)0.622 (1)0.050 (1)
C150.8971 (2)0.0111 (2)0.813 (1)0.055 (1)
C160.8467 (2)0.0211 (2)0.836 (1)0.057 (1)
C170.8029 (2)0.0156 (2)0.671 (1)0.051 (1)
H10.56630.18520.04200.093*
H2a0.64050.08020.21260.068*
H2b0.68680.12940.17570.068*
H30.64970.01090.05970.070*
H70.81070.11630.19320.056*
H80.85980.20320.23600.064*
H90.85630.27220.05930.064*
H100.80260.25610.39310.066*
H110.75220.16940.43960.059*
H130.86620.07640.32300.052*
H140.93810.06890.60640.060*
H150.92620.00810.92560.066*
H160.84240.04650.96190.068*
H170.76920.03720.68860.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.058 (2)0.073 (2)0.101 (3)0.025 (2)0.024 (2)0.040 (2)
O20.104 (3)0.098 (3)0.088 (3)0.047 (3)0.025 (3)0.029 (3)
N10.045 (2)0.039 (2)0.068 (3)0.005 (1)0.007 (2)0.001 (2)
N20.049 (2)0.038 (2)0.080 (3)0.004 (1)0.008 (2)0.005 (2)
C10.042 (2)0.046 (2)0.082 (4)0.004 (2)0.003 (2)0.016 (3)
C20.048 (2)0.052 (2)0.069 (3)0.008 (2)0.005 (2)0.013 (2)
C30.052 (2)0.044 (2)0.080 (4)0.007 (2)0.012 (3)0.003 (2)
C40.042 (2)0.032 (2)0.054 (2)0.002 (1)0.001 (2)0.000 (2)
C50.039 (2)0.036 (2)0.051 (2)0.007 (1)0.004 (2)0.006 (2)
C60.040 (2)0.031 (2)0.044 (2)0.007 (1)0.002 (2)0.002 (2)
C70.052 (2)0.044 (2)0.043 (2)0.006 (2)0.006 (2)0.005 (2)
C80.051 (2)0.056 (2)0.052 (2)0.000 (2)0.003 (2)0.013 (2)
C90.052 (2)0.042 (2)0.065 (3)0.006 (2)0.012 (2)0.008 (2)
C100.073 (3)0.039 (2)0.053 (3)0.001 (2)0.005 (2)0.005 (2)
C110.064 (2)0.039 (2)0.044 (2)0.005 (2)0.007 (2)0.003 (2)
C120.046 (2)0.030 (2)0.046 (2)0.002 (1)0.003 (2)0.003 (2)
C130.043 (2)0.042 (2)0.046 (2)0.003 (2)0.008 (2)0.002 (2)
C140.043 (2)0.047 (2)0.059 (3)0.000 (2)0.002 (2)0.005 (2)
C150.060 (3)0.053 (2)0.052 (2)0.007 (2)0.009 (2)0.002 (2)
C160.073 (3)0.046 (2)0.052 (3)0.001 (2)0.002 (2)0.010 (2)
C170.054 (2)0.041 (2)0.058 (3)0.008 (2)0.001 (2)0.003 (2)
Geometric parameters (Å, º) top
O1—C11.285 (6)C13—C141.390 (7)
O2—C11.192 (8)C14—C151.375 (7)
N1—C31.337 (6)C15—C161.384 (7)
N1—C51.384 (6)C16—C171.379 (7)
N1—C21.466 (6)O1—H10.82
N2—C31.311 (7)C2—H2a0.97
N2—C41.394 (5)C2—H2b0.97
C1—C21.538 (8)C3—H30.93
C4—C51.371 (6)C7—H70.93
C4—C121.473 (6)C8—H80.93
C5—C61.486 (5)C9—H90.93
C6—C111.387 (6)C10—H100.93
C6—C71.397 (6)C11—H110.93
C7—C81.384 (6)C13—H130.93
C8—C91.384 (7)C14—H140.93
C9—C101.364 (8)C15—H150.93
C10—C111.399 (6)C16—H160.93
C12—C131.398 (5)C17—H170.93
C12—C171.403 (6)
C2—N1—C3125.2 (4)C12—C17—C16121.2 (4)
C2—N1—C5125.2 (3)C1—O1—H1109.5
C3—N1—C5107.6 (4)N1—C2—H2a109.8
C3—N2—C4106.5 (4)C1—C2—H2a109.8
O1—C1—O2126.2 (6)N1—C2—H2b109.8
O1—C1—C2111.4 (5)C1—C2—H2b109.8
O2—C1—C2122.4 (5)H2a—C2—H2b108.2
N1—C2—C1109.5 (5)N2—C3—H3124.2
N1—C3—N2111.6 (4)N1—C3—H3124.2
N2—C4—C5108.2 (4)C8—C7—H7120.1
N2—C4—C12122.2 (4)C6—C7—H7120.1
C5—C4—C12129.7 (3)C9—C8—H8119.9
N1—C5—C4106.1 (3)C7—C8—H8119.9
N1—C5—C6121.8 (4)C10—C9—H9119.8
C4—C5—C6132.1 (4)C8—C9—H9119.8
C5—C6—C11120.0 (4)C9—C10—H10119.9
C7—C6—C11119.4 (4)C11—C10—H10119.9
C5—C6—C7120.6 (4)C6—C11—H11120.0
C6—C7—C8119.8 (4)C10—C11—H11120.0
C7—C8—C9120.3 (5)C14—C13—H13119.7
C8—C9—C10120.4 (4)C12—C13—H13119.7
C9—C10—C11120.1 (4)C15—C14—H14119.8
C6—C11—C10119.9 (4)C13—C14—H14119.8
C13—C12—C17117.7 (4)C14—C15—H15120.0
C4—C12—C13121.3 (4)C16—C15—H15120.0
C4—C12—C17121.0 (4)C17—C16—H16120.0
C12—C13—C14120.7 (4)C15—C16—H16120.0
C13—C14—C15120.3 (4)C16—C17—H17119.4
C14—C15—C16120.0 (5)C12—C17—H17119.4
C15—C16—C17120.0 (5)
C3—N1—C2—C180.5 (6)C11—C6—C7—C81.6 (6)
C5—N1—C2—C181.4 (6)C5—C6—C7—C8177.0 (4)
O2—C1—C2—N113.6 (7)C6—C7—C8—C90.2 (7)
O1—C1—C2—N1168.3 (4)C7—C8—C9—C100.9 (7)
C4—N2—C3—N10.8 (6)C8—C9—C10—C110.7 (7)
C5—N1—C3—N21.6 (6)C7—C6—C11—C101.9 (6)
C2—N1—C3—N2166.2 (5)C5—C6—C11—C10176.8 (4)
C3—N2—C4—C50.4 (6)C9—C10—C11—C60.7 (7)
C3—N2—C4—C12180.0 (4)C5—C4—C12—C1324.3 (7)
N2—C4—C5—N11.3 (5)N2—C4—C12—C13156.0 (4)
C12—C4—C5—N1179.0 (4)C5—C4—C12—C17154.4 (5)
N2—C4—C5—C6179.9 (4)N2—C4—C12—C1725.2 (6)
C12—C4—C5—C60.2 (8)C17—C12—C13—C143.2 (6)
C3—N1—C5—C41.8 (5)C4—C12—C13—C14175.6 (4)
C2—N1—C5—C4166.3 (5)C12—C13—C14—C151.9 (6)
C3—N1—C5—C6179.3 (4)C13—C14—C15—C160.6 (7)
C2—N1—C5—C614.7 (7)C14—C15—C16—C171.7 (8)
C4—C5—C6—C1172.5 (6)C15—C16—C17—C120.4 (7)
N1—C5—C6—C11108.8 (5)C13—C12—C17—C162.0 (6)
C4—C5—C6—C7106.0 (6)C4—C12—C17—C16176.8 (4)
N1—C5—C6—C772.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.821.792.602 (6)168
Symmetry code: (i) y+1/2, x1/2, z+1/2.
 

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