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The title compound, C14H11ClFNO, forms an intra­molecular O—H...N hydrogen bond. The dihedral angle between the two benzene rings is 71.6 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016588/bi2010sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016588/bi2010Isup2.hkl
Contains datablock I

CCDC reference: 610697

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.171
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C14 .. 5.19 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

4-Chloro-2-[(E)-(4-fluorophenyl)methyliminomethyl]phenol top
Crystal data top
C14H11ClFNOF(000) = 544
Mr = 263.69Dx = 1.388 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2681 reflections
a = 15.0408 (17) Åθ = 2.8–23.4°
b = 6.0375 (7) ŵ = 0.30 mm1
c = 14.3943 (17) ÅT = 292 K
β = 105.068 (2)°Block, yellow
V = 1262.2 (3) Å30.36 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2875 independent reflections
Radiation source: fine-focus sealed tube1922 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
φ and ω scansθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.930, Tmax = 0.942k = 77
10448 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0827P)2 + 0.0486P]
where P = (Fo2 + 2Fc2)/3
2875 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
Cl10.24851 (5)0.68464 (14)0.06470 (6)0.1139 (4)
F11.01699 (12)0.7386 (3)0.04864 (15)0.1338 (7)
O10.59803 (11)0.2130 (2)0.12348 (11)0.0750 (5)
H10.64080.28830.15470.113*
N10.67799 (12)0.5609 (3)0.21486 (12)0.0701 (5)
C10.51900 (14)0.3260 (3)0.11112 (13)0.0549 (5)
C20.43718 (16)0.2283 (3)0.05959 (14)0.0631 (5)
H20.43820.08650.03460.076*
C30.35561 (16)0.3385 (4)0.04549 (14)0.0682 (6)
H30.30140.27230.01060.082*
C40.35354 (14)0.5480 (4)0.08295 (14)0.0654 (5)
C50.43266 (14)0.6485 (3)0.13421 (13)0.0587 (5)
H50.43030.78930.15960.070*
C60.51639 (12)0.5403 (3)0.14833 (11)0.0518 (4)
C70.60011 (15)0.6532 (3)0.19967 (13)0.0612 (5)
H70.59630.79660.22190.073*
C80.75936 (17)0.6890 (5)0.26676 (18)0.0906 (8)
H8A0.78720.61870.32800.109*
H8B0.74070.83740.27940.109*
C90.82871 (13)0.7014 (4)0.20768 (15)0.0655 (5)
C100.83342 (14)0.8849 (4)0.15260 (16)0.0726 (6)
H100.79341.00260.15210.087*
C110.89599 (16)0.8981 (4)0.09819 (17)0.0813 (7)
H110.89841.02220.06060.098*
C120.95383 (16)0.7260 (4)0.10077 (19)0.0813 (7)
C130.95139 (16)0.5403 (4)0.1529 (2)0.0885 (7)
H130.99160.42350.15250.106*
C140.88822 (16)0.5291 (4)0.20623 (17)0.0807 (7)
H140.88550.40250.24220.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0866 (5)0.1295 (7)0.1138 (6)0.0373 (4)0.0049 (4)0.0163 (4)
F10.1051 (12)0.1633 (17)0.1581 (17)0.0184 (12)0.0791 (13)0.0171 (13)
O10.0796 (10)0.0618 (8)0.0949 (11)0.0041 (7)0.0427 (8)0.0076 (7)
N10.0696 (11)0.0839 (12)0.0617 (10)0.0179 (10)0.0258 (8)0.0046 (9)
C10.0747 (12)0.0484 (10)0.0505 (10)0.0029 (8)0.0321 (9)0.0025 (8)
C20.0871 (15)0.0545 (10)0.0557 (11)0.0164 (10)0.0327 (10)0.0120 (8)
C30.0733 (14)0.0831 (15)0.0487 (11)0.0176 (11)0.0170 (10)0.0038 (10)
C40.0721 (13)0.0717 (13)0.0511 (11)0.0087 (10)0.0140 (9)0.0114 (10)
C50.0794 (13)0.0474 (10)0.0514 (11)0.0045 (9)0.0206 (10)0.0051 (8)
C60.0701 (12)0.0474 (10)0.0426 (9)0.0067 (8)0.0228 (8)0.0027 (7)
C70.0774 (14)0.0607 (11)0.0518 (11)0.0130 (10)0.0283 (10)0.0061 (8)
C80.0767 (15)0.125 (2)0.0732 (15)0.0332 (14)0.0251 (12)0.0204 (14)
C90.0540 (11)0.0785 (14)0.0600 (12)0.0127 (10)0.0077 (9)0.0066 (10)
C100.0596 (12)0.0681 (13)0.0861 (15)0.0017 (10)0.0120 (11)0.0023 (11)
C110.0756 (15)0.0806 (15)0.0878 (16)0.0103 (12)0.0215 (12)0.0141 (13)
C120.0607 (13)0.0983 (18)0.0896 (17)0.0133 (12)0.0282 (12)0.0101 (14)
C130.0649 (14)0.0821 (16)0.114 (2)0.0134 (12)0.0154 (14)0.0080 (14)
C140.0788 (15)0.0740 (14)0.0817 (16)0.0070 (12)0.0070 (12)0.0139 (11)
Geometric parameters (Å, º) top
Cl1—C41.741 (2)C6—C71.453 (2)
F1—C121.357 (3)C7—H70.930
O1—C11.342 (2)C8—C91.509 (3)
O1—H10.820C8—H8A0.970
N1—C71.264 (3)C8—H8B0.970
N1—C81.476 (3)C9—C101.375 (3)
C1—C21.392 (3)C9—C141.376 (3)
C1—C61.405 (2)C10—C111.374 (3)
C2—C31.364 (3)C10—H100.930
C2—H20.930C11—C121.350 (3)
C3—C41.378 (3)C11—H110.930
C3—H30.930C12—C131.355 (4)
C4—C51.368 (3)C13—C141.369 (3)
C5—C61.386 (3)C13—H130.930
C5—H50.930C14—H140.930
C1—O1—H1109.5N1—C8—H8A109.6
C7—N1—C8117.8 (2)C9—C8—H8A109.6
O1—C1—C2119.04 (17)N1—C8—H8B109.6
O1—C1—C6121.95 (18)C9—C8—H8B109.6
C2—C1—C6119.01 (19)H8A—C8—H8B108.1
C3—C2—C1120.59 (18)C10—C9—C14118.0 (2)
C3—C2—H2119.7C10—C9—C8120.8 (2)
C1—C2—H2119.7C14—C9—C8121.2 (2)
C2—C3—C4120.0 (2)C11—C10—C9121.4 (2)
C2—C3—H3120.0C11—C10—H10119.3
C4—C3—H3120.0C9—C10—H10119.3
C5—C4—C3120.9 (2)C12—C11—C10118.1 (2)
C5—C4—Cl1119.95 (17)C12—C11—H11120.9
C3—C4—Cl1119.20 (18)C10—C11—H11120.9
C4—C5—C6119.99 (18)C11—C12—C13122.8 (2)
C4—C5—H5120.0C11—C12—F1118.7 (2)
C6—C5—H5120.0C13—C12—F1118.5 (2)
C5—C6—C1119.51 (17)C12—C13—C14118.3 (2)
C5—C6—C7119.19 (17)C12—C13—H13120.9
C1—C6—C7121.29 (18)C14—C13—H13120.9
N1—C7—C6121.52 (18)C13—C14—C9121.3 (2)
N1—C7—H7119.2C13—C14—H14119.3
C6—C7—H7119.2C9—C14—H14119.3
N1—C8—C9110.14 (18)
O1—C1—C2—C3179.87 (15)C1—C6—C7—N11.8 (3)
C6—C1—C2—C30.1 (3)C7—N1—C8—C9124.1 (2)
C1—C2—C3—C40.5 (3)N1—C8—C9—C1098.2 (3)
C2—C3—C4—C50.2 (3)N1—C8—C9—C1481.0 (3)
C2—C3—C4—Cl1179.57 (15)C14—C9—C10—C110.6 (3)
C3—C4—C5—C60.5 (3)C8—C9—C10—C11179.8 (2)
Cl1—C4—C5—C6179.64 (13)C9—C10—C11—C120.6 (4)
C4—C5—C6—C11.1 (3)C10—C11—C12—C131.4 (4)
C4—C5—C6—C7177.57 (16)C10—C11—C12—F1178.9 (2)
O1—C1—C6—C5179.37 (15)C11—C12—C13—C140.9 (4)
C2—C1—C6—C50.9 (2)F1—C12—C13—C14179.3 (2)
O1—C1—C6—C72.0 (2)C12—C13—C14—C90.3 (4)
C2—C1—C6—C7177.77 (16)C10—C9—C14—C131.0 (3)
C8—N1—C7—C6179.40 (17)C8—C9—C14—C13179.8 (2)
C5—C6—C7—N1179.55 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.882.601 (2)147
 

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