Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007604/rz2005sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007604/rz2005Isup2.hkl
Contains datablock I

CCDC reference: 605161

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 top

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) top
Crystal data top
C9H7NO·C4H6N2F(000) = 480
Mr = 227.26Dx = 1.245 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 878 reflections
a = 7.259 (3) Åθ = 3.0–15.9°
b = 9.109 (3) ŵ = 0.08 mm1
c = 18.334 (7) ÅT = 292 K
V = 1212.3 (8) Å3Block, colourless
Z = 40.20 × 0.10 × 0.02 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1537 independent reflections
Radiation source: fine focus sealed Siemens Mo tube900 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.100
0.3° wide ω exposures scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 99
Tmin = 0.984, Tmax = 0.998k = 1110
10211 measured reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0561P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.003
1537 reflectionsΔρmax = 0.12 e Å3
156 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (4)
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.2349 (5)0.5184 (4)1.02759 (19)0.0472 (10)
C20.3940 (5)0.4752 (4)1.06545 (19)0.0511 (10)
C30.5260 (6)0.3963 (5)1.0297 (2)0.0650 (12)
H30.63030.36501.05480.078*
C40.5056 (6)0.3619 (5)0.9556 (3)0.0736 (13)
H40.59770.30920.93190.088*
C50.3548 (6)0.4040 (5)0.9179 (2)0.0683 (13)
H50.34410.38150.86860.082*
C60.2150 (6)0.4815 (4)0.9532 (2)0.0532 (10)
C70.0503 (6)0.5256 (5)0.9188 (2)0.0665 (12)
H70.02960.50140.87020.080*
C80.0777 (6)0.6030 (6)0.9562 (2)0.0741 (12)
H80.18620.63320.93380.089*
C90.0433 (6)0.6360 (5)1.0287 (2)0.0687 (12)
H90.13260.68921.05370.082*
C100.4529 (5)0.1854 (4)0.7478 (2)0.0495 (9)
C110.3617 (5)0.1030 (4)0.7966 (2)0.0574 (11)
H110.41780.04150.83050.069*
C120.1556 (5)0.2170 (5)0.73763 (19)0.0593 (11)
H120.04270.25240.72130.071*
C130.6539 (5)0.2049 (5)0.7329 (2)0.0788 (14)
H13A0.67780.18730.68210.118*
H13B0.72320.13660.76180.118*
H13C0.68980.30320.74510.118*
N10.1051 (4)0.5981 (4)1.06480 (15)0.0548 (9)
N20.3189 (4)0.2578 (3)0.71020 (15)0.0503 (8)
H20.33600.31890.67510.060*
N30.1750 (4)0.1213 (4)0.79010 (17)0.0631 (9)
O10.4083 (3)0.5123 (3)1.13640 (13)0.0678 (9)
H10.50520.48021.15290.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.049 (2)0.038 (2)0.054 (2)0.0006 (18)0.0014 (18)0.0050 (19)
C20.056 (2)0.051 (3)0.046 (2)0.008 (2)0.0021 (19)0.0003 (19)
C30.062 (3)0.065 (3)0.069 (3)0.017 (2)0.001 (2)0.003 (2)
C40.077 (3)0.074 (3)0.070 (3)0.018 (3)0.008 (2)0.013 (3)
C50.087 (3)0.062 (3)0.056 (2)0.000 (3)0.002 (2)0.012 (2)
C60.065 (3)0.042 (2)0.053 (2)0.005 (2)0.002 (2)0.004 (2)
C70.085 (3)0.062 (3)0.053 (2)0.002 (3)0.011 (2)0.001 (2)
C80.068 (3)0.087 (3)0.068 (3)0.009 (3)0.009 (2)0.013 (3)
C90.064 (3)0.082 (3)0.061 (3)0.021 (2)0.000 (2)0.013 (3)
C100.049 (2)0.053 (2)0.047 (2)0.0013 (19)0.0013 (19)0.002 (2)
C110.066 (3)0.055 (3)0.052 (2)0.002 (2)0.0017 (19)0.006 (2)
C120.042 (2)0.083 (3)0.053 (2)0.009 (2)0.0025 (18)0.005 (2)
C130.050 (2)0.088 (3)0.099 (4)0.012 (2)0.006 (2)0.018 (3)
N10.0529 (19)0.064 (2)0.0478 (18)0.0078 (19)0.0013 (15)0.0094 (17)
N20.0451 (17)0.061 (2)0.0445 (16)0.0105 (18)0.0053 (14)0.0081 (16)
N30.058 (2)0.077 (3)0.0541 (19)0.010 (2)0.0055 (16)0.008 (2)
O10.0641 (17)0.092 (2)0.0476 (15)0.0279 (16)0.0107 (13)0.0057 (15)
Geometric parameters (Å, º) top
C1—N11.371 (4)C9—N11.311 (5)
C1—C21.404 (5)C9—H90.9300
C1—C61.412 (5)C10—C111.343 (5)
C2—O11.348 (4)C10—N21.363 (4)
C2—C31.366 (5)C10—C131.495 (5)
C3—C41.403 (6)C11—N31.371 (5)
C3—H30.9300C11—H110.9300
C4—C51.350 (6)C12—N31.305 (4)
C4—H40.9300C12—N21.340 (4)
C5—C61.396 (5)C12—H120.9300
C5—H50.9300C13—H13A0.9600
C6—C71.410 (5)C13—H13B0.9600
C7—C81.352 (6)C13—H13C0.9600
C7—H70.9300N2—H20.8600
C8—C91.385 (6)O1—H10.8200
C8—H80.9300
N1—C1—C2117.9 (3)N1—C9—C8125.1 (4)
N1—C1—C6122.4 (3)N1—C9—H9117.4
C2—C1—C6119.7 (3)C8—C9—H9117.4
O1—C2—C3122.7 (4)C11—C10—N2104.8 (3)
O1—C2—C1118.1 (3)C11—C10—C13132.0 (3)
C3—C2—C1119.2 (3)N2—C10—C13123.2 (3)
C2—C3—C4120.5 (4)C10—C11—N3111.2 (3)
C2—C3—H3119.7C10—C11—H11124.4
C4—C3—H3119.7N3—C11—H11124.4
C5—C4—C3121.2 (4)N3—C12—N2111.5 (3)
C5—C4—H4119.4N3—C12—H12124.2
C3—C4—H4119.4N2—C12—H12124.2
C4—C5—C6119.7 (4)C10—C13—H13A109.5
C4—C5—H5120.1C10—C13—H13B109.5
C6—C5—H5120.1H13A—C13—H13B109.5
C5—C6—C7123.6 (4)C10—C13—H13C109.5
C5—C6—C1119.6 (4)H13A—C13—H13C109.5
C7—C6—C1116.8 (4)H13B—C13—H13C109.5
C8—C7—C6120.3 (4)C9—N1—C1116.9 (3)
C8—C7—H7119.8C12—N2—C10107.9 (3)
C6—C7—H7119.8C12—N2—H2126.0
C7—C8—C9118.4 (4)C10—N2—H2126.0
C7—C8—H8120.8C12—N3—C11104.6 (3)
C9—C8—H8120.8C2—O1—H1109.5
N1—C1—C2—O11.2 (6)C5—C6—C7—C8178.7 (4)
C6—C1—C2—O1180.0 (3)C1—C6—C7—C81.8 (6)
N1—C1—C2—C3179.7 (3)C6—C7—C8—C90.6 (7)
C6—C1—C2—C30.9 (6)C7—C8—C9—N10.0 (7)
O1—C2—C3—C4179.2 (4)N2—C10—C11—N30.5 (4)
C1—C2—C3—C41.7 (6)C13—C10—C11—N3179.7 (4)
C2—C3—C4—C50.9 (7)C8—C9—N1—C10.7 (7)
C3—C4—C5—C60.8 (7)C2—C1—N1—C9179.3 (4)
C4—C5—C6—C7177.9 (4)C6—C1—N1—C92.0 (6)
C4—C5—C6—C11.6 (6)N3—C12—N2—C100.7 (4)
N1—C1—C6—C5178.0 (4)C11—C10—N2—C120.1 (4)
C2—C1—C6—C50.7 (5)C13—C10—N2—C12179.2 (4)
N1—C1—C6—C72.5 (5)N2—C12—N3—C111.0 (4)
C2—C1—C6—C7178.8 (4)C10—C11—N3—C120.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg10.932.803.649 (6)151
O1—H1···N3i0.821.862.654 (4)162
N2—H2···O1ii0.862.452.989 (4)121
N2—H2···N1ii0.862.203.022 (4)160
Symmetry codes: (i) x+1/2, y+1/2, z+2; (ii) x+1/2, y+1, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds