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In the title compound, C16H11NO2, the ester group is twisted away from the quinoline benzene ring by 77.32 (4)°. Mol­ecules are linked into centrosymmetric R22(16) dimers by C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038499/ci2175sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038499/ci2175Isup2.hkl
Contains datablock I

CCDC reference: 624182

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.041
  • wR factor = 0.124
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

8-Quinolyl benzoate top
Crystal data top
C16H11NO2F(000) = 520
Mr = 249.26Dx = 1.358 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9086 reflections
a = 6.6322 (3) Åθ = 3.1–27.5°
b = 8.5401 (4) ŵ = 0.09 mm1
c = 21.5578 (10) ÅT = 153 K
β = 92.798 (1)°Block, yellow
V = 1219.57 (10) Å30.45 × 0.17 × 0.16 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2270 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
ω scansh = 88
11407 measured reflectionsk = 119
2784 independent reflectionsl = 2727
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)] = 0.041H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0826P)2 + 0.1478P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2784 reflectionsΔρmax = 0.31 e Å3
173 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (3)
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
O10.79840 (13)0.89881 (10)0.58479 (4)0.0266 (2)
O20.47816 (13)0.86158 (10)0.61232 (4)0.0276 (2)
N10.78656 (15)0.58040 (12)0.59980 (5)0.0262 (2)
C10.79117 (19)0.42696 (15)0.60518 (6)0.0314 (3)
H10.80760.38390.64570.038*
C20.77332 (19)0.32220 (15)0.55460 (7)0.0330 (3)
H20.77770.21240.56150.040*
C30.74986 (17)0.37977 (15)0.49603 (7)0.0296 (3)
H30.73680.31090.46150.036*
C40.74517 (17)0.54402 (14)0.48713 (6)0.0244 (3)
C50.72252 (18)0.61506 (16)0.42797 (6)0.0290 (3)
H50.70940.55150.39180.035*
C60.71936 (19)0.77428 (17)0.42235 (6)0.0310 (3)
H60.70240.82060.38240.037*
C70.74096 (18)0.87046 (15)0.47535 (6)0.0283 (3)
H70.74020.98120.47120.034*
C80.76288 (17)0.80344 (14)0.53252 (5)0.0235 (3)
C90.76500 (16)0.63914 (14)0.54095 (5)0.0219 (3)
C100.64562 (18)0.91120 (13)0.62413 (5)0.0228 (3)
C110.70917 (18)0.99690 (13)0.68175 (5)0.0243 (3)
C120.9070 (2)1.04809 (15)0.69339 (6)0.0309 (3)
H121.00671.02770.66430.037*
C130.9575 (2)1.12903 (16)0.74781 (7)0.0372 (3)
H131.09231.16360.75610.045*
C140.8116 (2)1.15949 (16)0.79005 (6)0.0358 (3)
H140.84651.21570.82710.043*
C150.6147 (2)1.10836 (16)0.77858 (6)0.0335 (3)
H150.51511.12940.80770.040*
C160.5637 (2)1.02666 (14)0.72461 (6)0.0289 (3)
H160.42920.99090.71680.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0312 (5)0.0226 (4)0.0263 (4)0.0036 (3)0.0053 (3)0.0055 (3)
O20.0283 (5)0.0286 (4)0.0258 (4)0.0005 (3)0.0012 (3)0.0013 (3)
N10.0246 (5)0.0270 (5)0.0269 (5)0.0016 (4)0.0013 (4)0.0009 (4)
C10.0271 (6)0.0287 (6)0.0388 (7)0.0022 (5)0.0038 (5)0.0079 (5)
C20.0237 (6)0.0212 (6)0.0545 (8)0.0004 (5)0.0063 (5)0.0007 (6)
C30.0190 (6)0.0268 (6)0.0432 (7)0.0025 (4)0.0033 (5)0.0129 (5)
C40.0155 (5)0.0280 (6)0.0300 (6)0.0004 (4)0.0031 (4)0.0076 (5)
C50.0213 (6)0.0414 (7)0.0245 (6)0.0002 (5)0.0025 (4)0.0104 (5)
C60.0262 (6)0.0444 (8)0.0226 (6)0.0025 (5)0.0032 (5)0.0034 (5)
C70.0280 (6)0.0275 (6)0.0298 (6)0.0018 (5)0.0048 (5)0.0019 (5)
C80.0231 (6)0.0239 (6)0.0239 (6)0.0001 (4)0.0042 (4)0.0050 (5)
C90.0169 (5)0.0240 (6)0.0251 (6)0.0007 (4)0.0029 (4)0.0026 (4)
C100.0290 (6)0.0171 (5)0.0222 (5)0.0024 (4)0.0017 (4)0.0031 (4)
C110.0316 (6)0.0188 (5)0.0224 (5)0.0022 (5)0.0004 (5)0.0009 (4)
C120.0342 (7)0.0295 (6)0.0291 (6)0.0010 (5)0.0021 (5)0.0014 (5)
C130.0400 (8)0.0357 (7)0.0350 (7)0.0034 (6)0.0058 (6)0.0046 (6)
C140.0528 (8)0.0296 (6)0.0243 (6)0.0007 (6)0.0045 (6)0.0051 (5)
C150.0464 (8)0.0301 (7)0.0244 (6)0.0055 (5)0.0047 (5)0.0019 (5)
C160.0337 (6)0.0271 (6)0.0260 (6)0.0027 (5)0.0019 (5)0.0004 (5)
Geometric parameters (Å, º) top
O1—C101.3569 (15)C6—H60.95
O1—C81.4010 (14)C7—C81.3602 (17)
O2—C101.2043 (14)C7—H70.95
N1—C11.3157 (16)C8—C91.4148 (16)
N1—C91.3654 (15)C10—C111.4848 (16)
C1—C21.411 (2)C11—C161.3913 (18)
C1—H10.95C11—C121.3941 (18)
C2—C31.357 (2)C12—C131.3885 (18)
C2—H20.95C12—H120.95
C3—C41.4159 (17)C13—C141.385 (2)
C3—H30.95C13—H130.95
C4—C51.4136 (17)C14—C151.387 (2)
C4—C91.4172 (16)C14—H140.95
C5—C61.3652 (19)C15—C161.3844 (17)
C5—H50.95C15—H150.95
C6—C71.4088 (18)C16—H160.95
C10—O1—C8116.54 (9)O1—C8—C9118.23 (10)
C1—N1—C9116.67 (11)N1—C9—C8118.93 (10)
N1—C1—C2124.24 (12)N1—C9—C4123.46 (11)
N1—C1—H1117.9C8—C9—C4117.61 (11)
C2—C1—H1117.9O2—C10—O1123.34 (10)
C3—C2—C1119.39 (12)O2—C10—C11124.85 (11)
C3—C2—H2120.3O1—C10—C11111.79 (10)
C1—C2—H2120.3C16—C11—C12120.00 (11)
C2—C3—C4119.07 (11)C16—C11—C10117.89 (11)
C2—C3—H3120.5C12—C11—C10122.10 (11)
C4—C3—H3120.5C13—C12—C11119.62 (13)
C5—C4—C3123.24 (11)C13—C12—H12120.2
C5—C4—C9119.61 (11)C11—C12—H12120.2
C3—C4—C9117.16 (11)C14—C13—C12120.09 (13)
C6—C5—C4120.54 (11)C14—C13—H13120.0
C6—C5—H5119.7C12—C13—H13120.0
C4—C5—H5119.7C13—C14—C15120.35 (12)
C5—C6—C7120.54 (12)C13—C14—H14119.8
C5—C6—H6119.7C15—C14—H14119.8
C7—C6—H6119.7C16—C15—C14119.83 (13)
C8—C7—C6119.45 (12)C16—C15—H15120.1
C8—C7—H7120.3C14—C15—H15120.1
C6—C7—H7120.3C15—C16—C11120.10 (12)
C7—C8—O1119.38 (11)C15—C16—H16120.0
C7—C8—C9122.25 (11)C11—C16—H16120.0
C9—N1—C1—C20.68 (19)C5—C4—C9—N1179.69 (10)
N1—C1—C2—C30.0 (2)C3—C4—C9—N10.47 (17)
C1—C2—C3—C40.40 (18)C5—C4—C9—C80.56 (16)
C2—C3—C4—C5179.64 (11)C3—C4—C9—C8179.28 (10)
C2—C3—C4—C90.20 (17)C8—O1—C10—O29.49 (15)
C3—C4—C5—C6179.91 (11)C8—O1—C10—C11172.29 (9)
C9—C4—C5—C60.08 (17)O2—C10—C11—C162.07 (17)
C4—C5—C6—C70.74 (19)O1—C10—C11—C16176.11 (10)
C5—C6—C7—C80.72 (19)O2—C10—C11—C12178.38 (11)
C6—C7—C8—O1175.59 (10)O1—C10—C11—C123.44 (15)
C6—C7—C8—C90.04 (18)C16—C11—C12—C130.15 (18)
C10—O1—C8—C7109.82 (12)C10—C11—C12—C13179.39 (11)
C10—O1—C8—C974.46 (13)C11—C12—C13—C140.4 (2)
C1—N1—C9—C8178.85 (11)C12—C13—C14—C150.5 (2)
C1—N1—C9—C40.89 (17)C13—C14—C15—C160.1 (2)
C7—C8—C9—N1179.66 (10)C14—C15—C16—C110.48 (19)
O1—C8—C9—N14.75 (16)C12—C11—C16—C150.60 (18)
C7—C8—C9—C40.59 (17)C10—C11—C16—C15178.96 (11)
O1—C8—C9—C4175.00 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.553.4128 (15)151
Symmetry code: (i) x+1, y+1, z+1.
 

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