Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C
10H
10N
2O, 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
CCDC reference: 170314
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (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
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.
Crystal data top
C10H10N2O | F(000) = 368 |
Mr = 174.20 | Dx = 1.300 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
a = 6.3521 (7) Å | Cell parameters from 4184 reflections |
b = 10.4406 (6) Å | θ = 2.5–30.5° |
c = 13.523 (1) Å | µ = 0.09 mm−1 |
β = 97.199 (4)° | T = 123 K |
V = 889.8 (1) Å3 | Prism, colourless |
Z = 4 | 0.34 × 0.24 × 0.10 mm |
Data collection top
Rigaku RAXIS-RAPID Imaging Plate diffractometer | Rint = 0.029 |
Radiation source: X-ray tube | θmax = 30.5° |
ω scans | h = −9→9 |
10607 measured reflections | k = −14→14 |
2704 independent reflections | l = −19→17 |
2439 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | H-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) = 0.157 | Δρmax = 0.38 e Å−3 |
S = 1.60 | Δρmin = −0.36 e Å−3 |
2704 reflections | Extinction correction: Zachariasen (1967) type 2, Gaussian isotropic |
119 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | −0.2749 (1) | 0.16963 (6) | 0.33342 (6) | 0.0241 (2) | |
N1 | 0.0981 (1) | 0.03025 (7) | 0.32829 (5) | 0.0169 (2) | |
N2 | 0.0115 (1) | −0.13166 (7) | 0.22629 (6) | 0.0233 (2) | |
C1 | −0.0520 (2) | −0.05760 (8) | 0.29573 (7) | 0.0222 (2) | |
C2 | 0.2115 (2) | −0.08888 (9) | 0.21275 (7) | 0.0235 (2) | |
C3 | 0.2675 (1) | 0.01070 (9) | 0.27538 (7) | 0.0211 (2) | |
C4 | 0.0839 (1) | 0.12845 (8) | 0.40054 (6) | 0.0172 (2) | |
C5 | −0.1038 (1) | 0.19957 (8) | 0.39922 (7) | 0.0192 (2) | |
C6 | −0.1052 (2) | 0.30069 (9) | 0.46693 (7) | 0.0248 (2) | |
C7 | 0.0734 (2) | 0.32893 (9) | 0.53333 (7) | 0.0262 (2) | |
C8 | 0.2600 (2) | 0.25832 (9) | 0.53517 (6) | 0.0228 (2) | |
C9 | 0.2620 (1) | 0.15724 (8) | 0.46796 (6) | 0.0197 (2) | |
C10 | 0.4513 (2) | 0.2894 (1) | 0.60828 (8) | 0.0320 (3) | |
H1 | −0.1880 | −0.0657 | 0.3227 | 0.0321* | |
H1o | −0.3615 | 0.2447 | 0.3157 | 0.0321* | |
H2 | 0.2909 | −0.1314 | 0.1642 | 0.0321* | |
H3 | 0.3923 | 0.0618 | 0.2889 | 0.0321* | |
H6 | −0.2373 | 0.3515 | 0.4623 | 0.0321* | |
H7 | 0.0701 | 0.4033 | 0.5810 | 0.0321* | |
H9 | 0.3901 | 0.1050 | 0.4670 | 0.0321* | |
H10 | 0.5679 | 0.2312 | 0.5984 | 0.0321* | |
H11 | 0.4196 | 0.2775 | 0.6737 | 0.0321* | |
H12 | 0.4965 | 0.3748 | 0.6008 | 0.0321* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0184 (3) | 0.0179 (3) | 0.0354 (4) | 0.0017 (2) | 0.0014 (3) | 0.0018 (3) |
N1 | 0.0177 (4) | 0.0134 (3) | 0.0194 (4) | 0.0004 (2) | 0.0016 (3) | −0.0011 (2) |
N2 | 0.0235 (4) | 0.0169 (4) | 0.0288 (4) | −0.0019 (3) | 0.0011 (3) | −0.0036 (3) |
C1 | 0.0228 (4) | 0.0156 (4) | 0.0287 (4) | −0.0044 (3) | 0.0052 (3) | −0.0008 (3) |
C2 | 0.0209 (4) | 0.0220 (4) | 0.0274 (4) | 0.0009 (3) | 0.0020 (3) | −0.0067 (3) |
C3 | 0.0160 (4) | 0.0209 (4) | 0.0263 (4) | 0.0003 (3) | 0.0027 (3) | −0.0048 (3) |
C4 | 0.0214 (4) | 0.0131 (3) | 0.0175 (4) | 0.0007 (3) | 0.0042 (3) | 0.0011 (3) |
C5 | 0.0206 (4) | 0.0150 (4) | 0.0231 (4) | 0.0005 (3) | 0.0067 (3) | 0.0032 (3) |
C6 | 0.0283 (5) | 0.0199 (4) | 0.0280 (5) | 0.0048 (3) | 0.0107 (4) | −0.0004 (3) |
C7 | 0.0387 (6) | 0.0201 (4) | 0.0213 (4) | 0.0007 (4) | 0.0093 (4) | −0.0034 (3) |
C8 | 0.0316 (5) | 0.0212 (4) | 0.0160 (4) | −0.0022 (3) | 0.0042 (3) | −0.0001 (3) |
C9 | 0.0244 (5) | 0.0176 (4) | 0.0170 (4) | 0.0009 (3) | 0.0018 (3) | 0.0006 (3) |
C10 | 0.0383 (6) | 0.0362 (6) | 0.0206 (4) | −0.0067 (4) | 0.0003 (4) | −0.0070 (4) |
Geometric parameters (Å, º) top
O1—C5 | 1.352 (1) | C4—C9 | 1.394 (1) |
O1—H1o | 0.970 | C5—C6 | 1.398 (1) |
N1—C1 | 1.356 (1) | C6—C7 | 1.388 (2) |
N1—C3 | 1.380 (1) | C6—H6 | 0.988 |
N1—C4 | 1.427 (1) | C7—C8 | 1.394 (2) |
N2—C1 | 1.318 (1) | C7—H7 | 1.011 |
N2—C2 | 1.380 (1) | C8—C9 | 1.394 (1) |
C1—H1 | 0.983 | C8—C10 | 1.502 (1) |
C2—C3 | 1.360 (1) | C9—H9 | 0.981 |
C2—H2 | 0.983 | C10—H10 | 0.980 |
C3—H3 | 0.954 | C10—H11 | 0.939 |
C4—C5 | 1.403 (1) | C10—H12 | 0.947 |
| | | |
O1···N2i | 2.629 (1) | N2···C5iv | 3.405 (1) |
O1···C3ii | 3.354 (1) | N2···C6iv | 3.507 (1) |
O1···C1i | 3.448 (1) | C1···C8v | 3.482 (1) |
O1···C10iii | 3.552 (1) | C3···C10iii | 3.516 (1) |
N1···C10iii | 3.546 (1) | C6···C10ii | 3.599 (2) |
| | | |
C5—O1—H1o | 111.1 | C4—C5—C6 | 117.82 (8) |
C1—N1—C3 | 107.08 (7) | C5—C6—C7 | 120.82 (9) |
C1—N1—C4 | 127.29 (8) | C5—C6—H6 | 116.1 |
C3—N1—C4 | 125.58 (7) | C7—C6—H6 | 123.1 |
C1—N2—C2 | 105.88 (8) | C6—C7—C8 | 121.59 (8) |
N1—C1—N2 | 111.25 (8) | C6—C7—H7 | 119.7 |
N1—C1—H1 | 123.5 | C8—C7—H7 | 118.7 |
N2—C1—H1 | 125.2 | C7—C8—C9 | 117.77 (9) |
N2—C2—C3 | 109.75 (8) | C7—C8—C10 | 120.89 (9) |
N2—C2—H2 | 120.0 | C9—C8—C10 | 121.33 (9) |
C3—C2—H2 | 130.2 | C4—C9—C8 | 121.14 (9) |
N1—C3—C2 | 106.03 (8) | C4—C9—H9 | 118.6 |
N1—C3—H3 | 120.0 | C8—C9—H9 | 120.3 |
C2—C3—H3 | 133.9 | C8—C10—H10 | 109.8 |
N1—C4—C5 | 119.89 (8) | C8—C10—H11 | 109.9 |
N1—C4—C9 | 119.15 (8) | C8—C10—H12 | 111.4 |
C5—C4—C9 | 120.85 (8) | H10—C10—H11 | 107.5 |
O1—C5—C4 | 119.86 (8) | H10—C10—H12 | 109.0 |
O1—C5—C6 | 122.32 (8) | H11—C10—H12 | 109.2 |
| | | |
O1—C5—C4—N1 | 4.1 (1) | C4—C5—O1—H1o | −150.8 |
O1—C5—C4—C9 | −179.74 (8) | C4—C5—C6—C7 | −0.3 (1) |
O1—C5—C6—C7 | −179.88 (8) | C4—C5—C6—H6 | 177.4 |
O1—C5—C6—H6 | −2.2 | C4—C9—C8—C7 | 0.6 (1) |
N1—C1—N2—C2 | −0.5 (1) | C4—C9—C8—C10 | 179.73 (8) |
N1—C3—C2—N2 | −0.3 (1) | C5—C4—C9—C8 | −0.8 (1) |
N1—C3—C2—H2 | −179.0 | C5—C4—C9—H9 | 179.6 |
N1—C4—C5—C6 | −175.58 (8) | C5—C6—C7—C8 | 0.1 (2) |
N1—C4—C9—C8 | 175.42 (8) | C5—C6—C7—H7 | 179.1 |
N1—C4—C9—H9 | −4.2 | C6—C5—O1—H1o | 28.8 |
N2—C1—N1—C3 | 0.3 (1) | C6—C5—C4—C9 | 0.6 (1) |
N2—C1—N1—C4 | 178.03 (8) | C6—C7—C8—C9 | −0.2 (1) |
N2—C2—C3—H3 | 177.5 | C6—C7—C8—C10 | −179.36 (9) |
C1—N1—C3—C2 | 0.00 (10) | C7—C8—C9—H9 | −179.8 |
C1—N1—C3—H3 | −178.2 | C7—C8—C10—H10 | −179.2 |
C1—N1—C4—C5 | −42.3 (1) | C7—C8—C10—H11 | 62.7 |
C1—N1—C4—C9 | 141.42 (9) | C7—C8—C10—H12 | −58.5 |
C1—N2—C2—C3 | 0.5 (1) | C8—C7—C6—H6 | −177.4 |
C1—N2—C2—H2 | 179.4 | C9—C8—C7—H7 | −179.2 |
C2—N2—C1—H1 | −178.6 | C9—C8—C10—H10 | 1.6 |
C2—C3—N1—C4 | −177.75 (8) | C9—C8—C10—H11 | −116.5 |
C3—N1—C1—H1 | 178.4 | C9—C8—C10—H12 | 122.4 |
C3—N1—C4—C5 | 134.97 (9) | C10—C8—C7—H7 | 1.6 |
C3—N1—C4—C9 | −41.3 (1) | C10—C8—C9—H9 | −0.7 |
C4—N1—C1—H1 | −3.9 | H2—C2—C3—H3 | −1.3 |
C4—N1—C3—H3 | 4.1 | H6—C6—C7—H7 | 1.6 |
Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x−1/2, y−1/2, −z+1/2; (v) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N2i | 0.97 | 1.662 | 2.629 (1) | 174 |
Symmetry code: (i) −x−1/2, y+1/2, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.