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The title compound, C10H10N2O, was synthesized to investigate the structure of the Tyr–His residue in the active site of cytochrome c oxidase (CcO). The dihedral angle between the cresol and imidazole moieties is 42.21 (4)°, which is similar to that of the tyrosine-linked histidine in bovine heart CcO. In the title compound, the R and S enantiomers of axial chirality are connected by an O—H...N hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008492/ob6043sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008492/ob6043Isup2.hkl
Contains datablock I

CCDC reference: 170314

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.049
  • wR factor = 0.157
  • Data-to-parameter ratio = 22.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: PROCESS-AUTO (Molecular Structure Corporation, 1996); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR88 (Burla et al., 1989); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C10H10N2OF(000) = 368
Mr = 174.20Dx = 1.300 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
a = 6.3521 (7) ÅCell parameters from 4184 reflections
b = 10.4406 (6) Åθ = 2.5–30.5°
c = 13.523 (1) ŵ = 0.09 mm1
β = 97.199 (4)°T = 123 K
V = 889.8 (1) Å3Prism, colourless
Z = 40.34 × 0.24 × 0.10 mm
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
Rint = 0.029
Radiation source: X-ray tubeθmax = 30.5°
ω scansh = 99
10607 measured reflectionsk = 1414
2704 independent reflectionsl = 1917
2439 reflections with I > 2σ(I)
Refinement top
Refinement on F2H-atom parameters not refined
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.06P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.049(Δ/σ)max = 0.001
wR(F2) = 0.157Δρmax = 0.38 e Å3
S = 1.60Δρmin = 0.36 e Å3
2704 reflectionsExtinction correction: Zachariasen (1967) type 2, Gaussian isotropic
119 parametersExtinction coefficient: 0.16 (2)
Special details top

Refinement. All non-hydrogen atoms were found to place in corrected position by Fourier synthesis and refined on F2 by full-matrix least squares using anisotropic displacement parameters. Refinement using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2749 (1)0.16963 (6)0.33342 (6)0.0241 (2)
N10.0981 (1)0.03025 (7)0.32829 (5)0.0169 (2)
N20.0115 (1)0.13166 (7)0.22629 (6)0.0233 (2)
C10.0520 (2)0.05760 (8)0.29573 (7)0.0222 (2)
C20.2115 (2)0.08888 (9)0.21275 (7)0.0235 (2)
C30.2675 (1)0.01070 (9)0.27538 (7)0.0211 (2)
C40.0839 (1)0.12845 (8)0.40054 (6)0.0172 (2)
C50.1038 (1)0.19957 (8)0.39922 (7)0.0192 (2)
C60.1052 (2)0.30069 (9)0.46693 (7)0.0248 (2)
C70.0734 (2)0.32893 (9)0.53333 (7)0.0262 (2)
C80.2600 (2)0.25832 (9)0.53517 (6)0.0228 (2)
C90.2620 (1)0.15724 (8)0.46796 (6)0.0197 (2)
C100.4513 (2)0.2894 (1)0.60828 (8)0.0320 (3)
H10.18800.06570.32270.0321*
H1o0.36150.24470.31570.0321*
H20.29090.13140.16420.0321*
H30.39230.06180.28890.0321*
H60.23730.35150.46230.0321*
H70.07010.40330.58100.0321*
H90.39010.10500.46700.0321*
H100.56790.23120.59840.0321*
H110.41960.27750.67370.0321*
H120.49650.37480.60080.0321*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0184 (3)0.0179 (3)0.0354 (4)0.0017 (2)0.0014 (3)0.0018 (3)
N10.0177 (4)0.0134 (3)0.0194 (4)0.0004 (2)0.0016 (3)0.0011 (2)
N20.0235 (4)0.0169 (4)0.0288 (4)0.0019 (3)0.0011 (3)0.0036 (3)
C10.0228 (4)0.0156 (4)0.0287 (4)0.0044 (3)0.0052 (3)0.0008 (3)
C20.0209 (4)0.0220 (4)0.0274 (4)0.0009 (3)0.0020 (3)0.0067 (3)
C30.0160 (4)0.0209 (4)0.0263 (4)0.0003 (3)0.0027 (3)0.0048 (3)
C40.0214 (4)0.0131 (3)0.0175 (4)0.0007 (3)0.0042 (3)0.0011 (3)
C50.0206 (4)0.0150 (4)0.0231 (4)0.0005 (3)0.0067 (3)0.0032 (3)
C60.0283 (5)0.0199 (4)0.0280 (5)0.0048 (3)0.0107 (4)0.0004 (3)
C70.0387 (6)0.0201 (4)0.0213 (4)0.0007 (4)0.0093 (4)0.0034 (3)
C80.0316 (5)0.0212 (4)0.0160 (4)0.0022 (3)0.0042 (3)0.0001 (3)
C90.0244 (5)0.0176 (4)0.0170 (4)0.0009 (3)0.0018 (3)0.0006 (3)
C100.0383 (6)0.0362 (6)0.0206 (4)0.0067 (4)0.0003 (4)0.0070 (4)
Geometric parameters (Å, º) top
O1—C51.352 (1)C4—C91.394 (1)
O1—H1o0.970C5—C61.398 (1)
N1—C11.356 (1)C6—C71.388 (2)
N1—C31.380 (1)C6—H60.988
N1—C41.427 (1)C7—C81.394 (2)
N2—C11.318 (1)C7—H71.011
N2—C21.380 (1)C8—C91.394 (1)
C1—H10.983C8—C101.502 (1)
C2—C31.360 (1)C9—H90.981
C2—H20.983C10—H100.980
C3—H30.954C10—H110.939
C4—C51.403 (1)C10—H120.947
O1···N2i2.629 (1)N2···C5iv3.405 (1)
O1···C3ii3.354 (1)N2···C6iv3.507 (1)
O1···C1i3.448 (1)C1···C8v3.482 (1)
O1···C10iii3.552 (1)C3···C10iii3.516 (1)
N1···C10iii3.546 (1)C6···C10ii3.599 (2)
C5—O1—H1o111.1C4—C5—C6117.82 (8)
C1—N1—C3107.08 (7)C5—C6—C7120.82 (9)
C1—N1—C4127.29 (8)C5—C6—H6116.1
C3—N1—C4125.58 (7)C7—C6—H6123.1
C1—N2—C2105.88 (8)C6—C7—C8121.59 (8)
N1—C1—N2111.25 (8)C6—C7—H7119.7
N1—C1—H1123.5C8—C7—H7118.7
N2—C1—H1125.2C7—C8—C9117.77 (9)
N2—C2—C3109.75 (8)C7—C8—C10120.89 (9)
N2—C2—H2120.0C9—C8—C10121.33 (9)
C3—C2—H2130.2C4—C9—C8121.14 (9)
N1—C3—C2106.03 (8)C4—C9—H9118.6
N1—C3—H3120.0C8—C9—H9120.3
C2—C3—H3133.9C8—C10—H10109.8
N1—C4—C5119.89 (8)C8—C10—H11109.9
N1—C4—C9119.15 (8)C8—C10—H12111.4
C5—C4—C9120.85 (8)H10—C10—H11107.5
O1—C5—C4119.86 (8)H10—C10—H12109.0
O1—C5—C6122.32 (8)H11—C10—H12109.2
O1—C5—C4—N14.1 (1)C4—C5—O1—H1o150.8
O1—C5—C4—C9179.74 (8)C4—C5—C6—C70.3 (1)
O1—C5—C6—C7179.88 (8)C4—C5—C6—H6177.4
O1—C5—C6—H62.2C4—C9—C8—C70.6 (1)
N1—C1—N2—C20.5 (1)C4—C9—C8—C10179.73 (8)
N1—C3—C2—N20.3 (1)C5—C4—C9—C80.8 (1)
N1—C3—C2—H2179.0C5—C4—C9—H9179.6
N1—C4—C5—C6175.58 (8)C5—C6—C7—C80.1 (2)
N1—C4—C9—C8175.42 (8)C5—C6—C7—H7179.1
N1—C4—C9—H94.2C6—C5—O1—H1o28.8
N2—C1—N1—C30.3 (1)C6—C5—C4—C90.6 (1)
N2—C1—N1—C4178.03 (8)C6—C7—C8—C90.2 (1)
N2—C2—C3—H3177.5C6—C7—C8—C10179.36 (9)
C1—N1—C3—C20.00 (10)C7—C8—C9—H9179.8
C1—N1—C3—H3178.2C7—C8—C10—H10179.2
C1—N1—C4—C542.3 (1)C7—C8—C10—H1162.7
C1—N1—C4—C9141.42 (9)C7—C8—C10—H1258.5
C1—N2—C2—C30.5 (1)C8—C7—C6—H6177.4
C1—N2—C2—H2179.4C9—C8—C7—H7179.2
C2—N2—C1—H1178.6C9—C8—C10—H101.6
C2—C3—N1—C4177.75 (8)C9—C8—C10—H11116.5
C3—N1—C1—H1178.4C9—C8—C10—H12122.4
C3—N1—C4—C5134.97 (9)C10—C8—C7—H71.6
C3—N1—C4—C941.3 (1)C10—C8—C9—H90.7
C4—N1—C1—H13.9H2—C2—C3—H31.3
C4—N1—C3—H34.1H6—C6—C7—H71.6
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x1, y, z; (iii) x1/2, y+1/2, z1/2; (iv) x1/2, y1/2, z+1/2; (v) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N2i0.971.6622.629 (1)174
Symmetry code: (i) x1/2, y+1/2, z+1/2.
 

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