A 1:1 cocrystal of 8-hydroxy­quinoline and 5-methyl-1H-imidazole

In the title compound, C₉H₇NO·C₄H₆N₂, the imidazole ring is twisted away from the quinoline ring system with a dihedral angle of 60.8 (1)°. The crystal packing is stabilized by N—H...O, N—H...N, O—H...N hydrogen bonds and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.059
• wR factor = 0.129
• Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.75 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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           27.00
           From the CIF: _reflns_number_total               1537
           Count of symmetry unique reflns         1542
           Completeness (_total/calc)             99.68%
           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
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

8-hydroxyquinoline–5-methyl-1H-imidazole (1/1)

Crystal data

C9H7NO·C4H6N2	F(000) = 480
Mr = 227.26	Dx = 1.245 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 878 reflections
a = 7.259 (3) Å	θ = 3.0–15.9°
b = 9.109 (3) Å	µ = 0.08 mm^−1
c = 18.334 (7) Å	T = 292 K
V = 1212.3 (8) Å^3	Block, colourless
Z = 4	0.20 × 0.10 × 0.02 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1537 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.100
0.3° wide ω exposures scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.984, Tmax = 0.998	k = −11→10
10211 measured reflections	l = −23→23

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0561P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.003
1537 reflections	Δρmax = 0.12 e Å^−3
156 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2349 (5)	0.5184 (4)	1.02759 (19)	0.0472 (10)
C2	0.3940 (5)	0.4752 (4)	1.06545 (19)	0.0511 (10)
C3	0.5260 (6)	0.3963 (5)	1.0297 (2)	0.0650 (12)
H3	0.6303	0.3650	1.0548	0.078*
C4	0.5056 (6)	0.3619 (5)	0.9556 (3)	0.0736 (13)
H4	0.5977	0.3092	0.9319	0.088*
C5	0.3548 (6)	0.4040 (5)	0.9179 (2)	0.0683 (13)
H5	0.3441	0.3815	0.8686	0.082*
C6	0.2150 (6)	0.4815 (4)	0.9532 (2)	0.0532 (10)
C7	0.0503 (6)	0.5256 (5)	0.9188 (2)	0.0665 (12)
H7	0.0296	0.5014	0.8702	0.080*
C8	−0.0777 (6)	0.6030 (6)	0.9562 (2)	0.0741 (12)
H8	−0.1862	0.6332	0.9338	0.089*
C9	−0.0433 (6)	0.6360 (5)	1.0287 (2)	0.0687 (12)
H9	−0.1326	0.6892	1.0537	0.082*
C10	0.4529 (5)	0.1854 (4)	0.7478 (2)	0.0495 (9)
C11	0.3617 (5)	0.1030 (4)	0.7966 (2)	0.0574 (11)
H11	0.4178	0.0415	0.8305	0.069*
C12	0.1556 (5)	0.2170 (5)	0.73763 (19)	0.0593 (11)
H12	0.0427	0.2524	0.7213	0.071*
C13	0.6539 (5)	0.2049 (5)	0.7329 (2)	0.0788 (14)
H13A	0.6778	0.1873	0.6821	0.118*
H13B	0.7232	0.1366	0.7618	0.118*
H13C	0.6898	0.3032	0.7451	0.118*
N1	0.1051 (4)	0.5981 (4)	1.06480 (15)	0.0548 (9)
N2	0.3189 (4)	0.2578 (3)	0.71020 (15)	0.0503 (8)
H2	0.3360	0.3189	0.6751	0.060*
N3	0.1750 (4)	0.1213 (4)	0.79010 (17)	0.0631 (9)
O1	0.4083 (3)	0.5123 (3)	1.13640 (13)	0.0678 (9)
H1	0.5052	0.4802	1.1529	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.049 (2)	0.038 (2)	0.054 (2)	0.0006 (18)	0.0014 (18)	0.0050 (19)
C2	0.056 (2)	0.051 (3)	0.046 (2)	0.008 (2)	−0.0021 (19)	0.0003 (19)
C3	0.062 (3)	0.065 (3)	0.069 (3)	0.017 (2)	−0.001 (2)	0.003 (2)
C4	0.077 (3)	0.074 (3)	0.070 (3)	0.018 (3)	0.008 (2)	−0.013 (3)
C5	0.087 (3)	0.062 (3)	0.056 (2)	0.000 (3)	−0.002 (2)	−0.012 (2)
C6	0.065 (3)	0.042 (2)	0.053 (2)	−0.005 (2)	−0.002 (2)	0.004 (2)
C7	0.085 (3)	0.062 (3)	0.053 (2)	−0.002 (3)	−0.011 (2)	0.001 (2)
C8	0.068 (3)	0.087 (3)	0.068 (3)	0.009 (3)	−0.009 (2)	0.013 (3)
C9	0.064 (3)	0.082 (3)	0.061 (3)	0.021 (2)	0.000 (2)	0.013 (3)
C10	0.049 (2)	0.053 (2)	0.047 (2)	0.0013 (19)	0.0013 (19)	−0.002 (2)
C11	0.066 (3)	0.055 (3)	0.052 (2)	−0.002 (2)	−0.0017 (19)	0.006 (2)
C12	0.042 (2)	0.083 (3)	0.053 (2)	−0.009 (2)	−0.0025 (18)	0.005 (2)
C13	0.050 (2)	0.088 (3)	0.099 (4)	0.012 (2)	0.006 (2)	0.018 (3)
N1	0.0529 (19)	0.064 (2)	0.0478 (18)	0.0078 (19)	−0.0013 (15)	0.0094 (17)
N2	0.0451 (17)	0.061 (2)	0.0445 (16)	−0.0105 (18)	0.0053 (14)	0.0081 (16)
N3	0.058 (2)	0.077 (3)	0.0541 (19)	−0.010 (2)	0.0055 (16)	0.008 (2)
O1	0.0641 (17)	0.092 (2)	0.0476 (15)	0.0279 (16)	−0.0107 (13)	−0.0057 (15)

Geometric parameters (Å, º)

C1—N1	1.371 (4)	C9—N1	1.311 (5)
C1—C2	1.404 (5)	C9—H9	0.9300
C1—C6	1.412 (5)	C10—C11	1.343 (5)
C2—O1	1.348 (4)	C10—N2	1.363 (4)
C2—C3	1.366 (5)	C10—C13	1.495 (5)
C3—C4	1.403 (6)	C11—N3	1.371 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.350 (6)	C12—N3	1.305 (4)
C4—H4	0.9300	C12—N2	1.340 (4)
C5—C6	1.396 (5)	C12—H12	0.9300
C5—H5	0.9300	C13—H13A	0.9600
C6—C7	1.410 (5)	C13—H13B	0.9600
C7—C8	1.352 (6)	C13—H13C	0.9600
C7—H7	0.9300	N2—H2	0.8600
C8—C9	1.385 (6)	O1—H1	0.8200
C8—H8	0.9300
N1—C1—C2	117.9 (3)	N1—C9—C8	125.1 (4)
N1—C1—C6	122.4 (3)	N1—C9—H9	117.4
C2—C1—C6	119.7 (3)	C8—C9—H9	117.4
O1—C2—C3	122.7 (4)	C11—C10—N2	104.8 (3)
O1—C2—C1	118.1 (3)	C11—C10—C13	132.0 (3)
C3—C2—C1	119.2 (3)	N2—C10—C13	123.2 (3)
C2—C3—C4	120.5 (4)	C10—C11—N3	111.2 (3)
C2—C3—H3	119.7	C10—C11—H11	124.4
C4—C3—H3	119.7	N3—C11—H11	124.4
C5—C4—C3	121.2 (4)	N3—C12—N2	111.5 (3)
C5—C4—H4	119.4	N3—C12—H12	124.2
C3—C4—H4	119.4	N2—C12—H12	124.2
C4—C5—C6	119.7 (4)	C10—C13—H13A	109.5
C4—C5—H5	120.1	C10—C13—H13B	109.5
C6—C5—H5	120.1	H13A—C13—H13B	109.5
C5—C6—C7	123.6 (4)	C10—C13—H13C	109.5
C5—C6—C1	119.6 (4)	H13A—C13—H13C	109.5
C7—C6—C1	116.8 (4)	H13B—C13—H13C	109.5
C8—C7—C6	120.3 (4)	C9—N1—C1	116.9 (3)
C8—C7—H7	119.8	C12—N2—C10	107.9 (3)
C6—C7—H7	119.8	C12—N2—H2	126.0
C7—C8—C9	118.4 (4)	C10—N2—H2	126.0
C7—C8—H8	120.8	C12—N3—C11	104.6 (3)
C9—C8—H8	120.8	C2—O1—H1	109.5
N1—C1—C2—O1	1.2 (6)	C5—C6—C7—C8	−178.7 (4)
C6—C1—C2—O1	180.0 (3)	C1—C6—C7—C8	1.8 (6)
N1—C1—C2—C3	−179.7 (3)	C6—C7—C8—C9	−0.6 (7)
C6—C1—C2—C3	−0.9 (6)	C7—C8—C9—N1	0.0 (7)
O1—C2—C3—C4	−179.2 (4)	N2—C10—C11—N3	0.5 (4)
C1—C2—C3—C4	1.7 (6)	C13—C10—C11—N3	179.7 (4)
C2—C3—C4—C5	−0.9 (7)	C8—C9—N1—C1	−0.7 (7)
C3—C4—C5—C6	−0.8 (7)	C2—C1—N1—C9	−179.3 (4)
C4—C5—C6—C7	−177.9 (4)	C6—C1—N1—C9	2.0 (6)
C4—C5—C6—C1	1.6 (6)	N3—C12—N2—C10	−0.7 (4)
N1—C1—C6—C5	178.0 (4)	C11—C10—N2—C12	0.1 (4)
C2—C1—C6—C5	−0.7 (5)	C13—C10—N2—C12	−179.2 (4)
N1—C1—C6—C7	−2.5 (5)	N2—C12—N3—C11	1.0 (4)
C2—C1—C6—C7	178.8 (4)	C10—C11—N3—C12	−0.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1	0.93	2.80	3.649 (6)	151
O1—H1···N3^i	0.82	1.86	2.654 (4)	162
N2—H2···O1^ii	0.86	2.45	2.989 (4)	121
N2—H2···N1^ii	0.86	2.20	3.022 (4)	160

Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) −x+1/2, −y+1, z−1/2.