2-(Imidazol-1-yl)-4-methyl­phenol

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.

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

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Computing details

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)

Crystal data

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) Å^3	Prism, colourless
Z = 4	0.34 × 0.24 × 0.10 mm

Data collection

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

Refinement on F^2	H-atom parameters not refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.06P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.049	(Δ/σ)max = 0.001
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···N2^i	2.629 (1)	N2···C5^iv	3.405 (1)
O1···C3^ii	3.354 (1)	N2···C6^iv	3.507 (1)
O1···C1^i	3.448 (1)	C1···C8^v	3.482 (1)
O1···C10^iii	3.552 (1)	C3···C10^iii	3.516 (1)
N1···C10^iii	3.546 (1)	C6···C10^ii	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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2^i	0.97	1.662	2.629 (1)	174

Symmetry code: (i) −x−1/2, y+1/2, −z+1/2.