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In the title compound, C16H11FO2, a synthetic isocoumarin, the benzene ring is not perpendicular to the planar isocoumarin ring sytem, the dihedral angle being 75.32 (3)°. Inter­molecular C—H...O hydrogen bonds may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047751/hk2161sup1.cif
Contains datablocks I, wy1589wc

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047751/hk2161Isup2.hkl
Contains datablock I

CCDC reference: 630007

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.125
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _diffrn_reflns_theta_full 28.30 From the CIF: _reflns_number_total 2883 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3103 Completeness (_total/calc) 92.91% PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick,1997); program(s) used to refine structure: SHELXL97 (Sheldrick,1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

3-(4-fluorobenzyl)isocoumarin top
Crystal data top
C16H11FO2F(000) = 528
Mr = 254.25Dx = 1.353 Mg m3
Monoclinic, P21/cMelting point: 181 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 16.3696 (16) ÅCell parameters from 2688 reflections
b = 5.5359 (5) Åθ = 2.7–28.2°
c = 14.1406 (14) ŵ = 0.10 mm1
β = 103.011 (2)°T = 294 K
V = 1248.5 (2) Å3Block, colorless
Z = 40.28 × 0.22 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2883 independent reflections
Radiation source: fine-focus sealed tube1969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω and φ scanθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1921
Tmin = 0.972, Tmax = 0.981k = 67
6998 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.062P)2 + 0.1403P]
where P = (Fo2 + 2Fc2)/3
2883 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.18 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
C10.40433 (11)0.0369 (4)0.39631 (13)0.0758 (5)
H1A0.41420.00790.46270.091*
C20.44394 (11)0.2241 (4)0.36180 (16)0.0862 (6)
H2A0.48090.32210.40490.103*
C30.42922 (11)0.2682 (3)0.26283 (15)0.0808 (5)
H3A0.45620.39620.24000.097*
C40.37529 (9)0.1250 (3)0.19836 (12)0.0653 (4)
H4A0.36610.15600.13220.078*
C50.33385 (8)0.0678 (3)0.23141 (10)0.0525 (3)
C60.34899 (9)0.1107 (3)0.33149 (10)0.0568 (4)
C70.30630 (9)0.3098 (3)0.36837 (9)0.0593 (4)
C80.23346 (8)0.3907 (3)0.20267 (9)0.0495 (3)
C90.27458 (8)0.2185 (3)0.16747 (9)0.0508 (3)
H9A0.26490.19520.10070.061*
C100.16733 (9)0.5567 (3)0.14890 (10)0.0568 (4)
H10A0.18830.72100.15680.068*
H10B0.11890.54720.17760.068*
C110.13989 (8)0.5018 (3)0.04170 (9)0.0489 (3)
C120.16609 (10)0.6406 (3)0.02631 (11)0.0647 (4)
H12A0.20180.77060.00620.078*
C130.14031 (12)0.5901 (3)0.12413 (12)0.0766 (5)
H13A0.15810.68510.16990.092*
C140.08860 (10)0.3994 (3)0.15222 (10)0.0626 (4)
C150.06171 (10)0.2551 (3)0.08801 (11)0.0678 (4)
H15A0.02670.12410.10890.081*
C160.08785 (10)0.3085 (3)0.00928 (10)0.0640 (4)
H16A0.06990.21160.05440.077*
F10.06264 (7)0.3504 (2)0.24905 (6)0.0987 (4)
O10.31681 (8)0.3727 (2)0.45168 (7)0.0818 (4)
O20.24844 (6)0.4374 (2)0.30111 (6)0.0590 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0673 (10)0.0874 (13)0.0648 (10)0.0087 (9)0.0014 (8)0.0201 (9)
C20.0670 (11)0.0790 (13)0.1033 (15)0.0047 (10)0.0006 (10)0.0278 (11)
C30.0617 (10)0.0664 (11)0.1093 (15)0.0047 (8)0.0089 (10)0.0001 (10)
C40.0545 (8)0.0643 (10)0.0747 (10)0.0002 (7)0.0092 (7)0.0090 (8)
C50.0471 (7)0.0561 (8)0.0527 (8)0.0080 (6)0.0079 (6)0.0016 (6)
C60.0519 (8)0.0656 (9)0.0497 (7)0.0106 (7)0.0045 (6)0.0066 (7)
C70.0640 (9)0.0743 (10)0.0377 (7)0.0102 (8)0.0078 (6)0.0021 (7)
C80.0556 (7)0.0558 (8)0.0359 (6)0.0053 (6)0.0076 (5)0.0056 (6)
C90.0529 (7)0.0585 (8)0.0394 (6)0.0031 (6)0.0073 (5)0.0055 (6)
C100.0639 (8)0.0562 (9)0.0481 (7)0.0046 (7)0.0079 (6)0.0062 (6)
C110.0511 (7)0.0492 (8)0.0443 (7)0.0046 (6)0.0063 (5)0.0009 (6)
C120.0741 (10)0.0571 (9)0.0585 (9)0.0089 (8)0.0056 (7)0.0101 (7)
C130.0939 (12)0.0828 (12)0.0530 (9)0.0007 (10)0.0163 (8)0.0241 (8)
C140.0689 (9)0.0738 (11)0.0398 (7)0.0189 (8)0.0007 (6)0.0005 (7)
C150.0705 (10)0.0694 (10)0.0571 (9)0.0099 (8)0.0007 (7)0.0078 (8)
C160.0738 (10)0.0677 (10)0.0493 (8)0.0171 (8)0.0114 (7)0.0022 (7)
F10.1212 (9)0.1238 (10)0.0405 (5)0.0281 (7)0.0045 (5)0.0061 (5)
O10.0999 (9)0.1064 (10)0.0367 (5)0.0066 (7)0.0101 (5)0.0049 (6)
O20.0671 (6)0.0717 (7)0.0371 (5)0.0025 (5)0.0093 (4)0.0074 (4)
Geometric parameters (Å, º) top
C1—C21.370 (3)C8—C101.491 (2)
C1—C61.398 (2)C9—H9A0.9300
C1—H1A0.9300C10—C111.5117 (18)
C2—C31.387 (3)C10—H10A0.9700
C2—H2A0.9300C10—H10B0.9700
C3—C41.370 (2)C11—C121.3728 (19)
C3—H3A0.9300C11—C161.380 (2)
C4—C51.400 (2)C12—C131.381 (2)
C4—H4A0.9300C12—H12A0.9300
C5—C61.4010 (19)C13—C141.355 (3)
C5—C91.4353 (19)C13—H13A0.9300
C6—C71.462 (2)C14—C151.355 (2)
C7—O11.2031 (16)C14—F11.3663 (15)
C7—O21.3766 (18)C15—C161.378 (2)
C8—C91.3269 (19)C15—H15A0.9300
C8—O21.3824 (14)C16—H16A0.9300
C2—C1—C6119.85 (17)C5—C9—H9A119.7
C2—C1—H1A120.1C8—C10—C11113.91 (11)
C6—C1—H1A120.1C8—C10—H10A108.8
C1—C2—C3120.26 (17)C11—C10—H10A108.8
C1—C2—H2A119.9C8—C10—H10B108.8
C3—C2—H2A119.9C11—C10—H10B108.8
C4—C3—C2120.60 (18)H10A—C10—H10B107.7
C4—C3—H3A119.7C12—C11—C16117.90 (13)
C2—C3—H3A119.7C12—C11—C10121.40 (13)
C3—C4—C5120.47 (16)C16—C11—C10120.70 (13)
C3—C4—H4A119.8C11—C12—C13121.02 (15)
C5—C4—H4A119.8C11—C12—H12A119.5
C4—C5—C6118.54 (14)C13—C12—H12A119.5
C4—C5—C9122.85 (13)C14—C13—C12118.75 (15)
C6—C5—C9118.58 (13)C14—C13—H13A120.6
C1—C6—C5120.28 (16)C12—C13—H13A120.6
C1—C6—C7119.85 (14)C15—C14—C13122.58 (14)
C5—C6—C7119.87 (13)C15—C14—F1118.66 (16)
O1—C7—O2116.90 (15)C13—C14—F1118.76 (15)
O1—C7—C6126.36 (15)C14—C15—C16117.89 (15)
O2—C7—C6116.74 (11)C14—C15—H15A121.1
C9—C8—O2121.47 (12)C16—C15—H15A121.1
C9—C8—C10128.52 (12)C15—C16—C11121.86 (14)
O2—C8—C10110.01 (11)C15—C16—H16A119.1
C8—C9—C5120.63 (12)C11—C16—H16A119.1
C8—C9—H9A119.7C7—O2—C8122.57 (11)
C6—C1—C2—C30.2 (3)C9—C8—C10—C115.8 (2)
C1—C2—C3—C40.3 (3)O2—C8—C10—C11173.76 (11)
C2—C3—C4—C50.3 (3)C8—C10—C11—C12103.74 (16)
C3—C4—C5—C60.2 (2)C8—C10—C11—C1675.84 (18)
C3—C4—C5—C9177.81 (14)C16—C11—C12—C130.8 (2)
C2—C1—C6—C50.0 (2)C10—C11—C12—C13179.60 (15)
C2—C1—C6—C7179.63 (15)C11—C12—C13—C140.3 (3)
C4—C5—C6—C10.1 (2)C12—C13—C14—C150.5 (3)
C9—C5—C6—C1178.02 (13)C12—C13—C14—F1179.58 (14)
C4—C5—C6—C7179.64 (13)C13—C14—C15—C160.7 (3)
C9—C5—C6—C71.6 (2)F1—C14—C15—C16179.39 (14)
C1—C6—C7—O14.3 (2)C14—C15—C16—C110.1 (3)
C5—C6—C7—O1176.14 (15)C12—C11—C16—C150.6 (2)
C1—C6—C7—O2175.69 (13)C10—C11—C16—C15179.79 (14)
C5—C6—C7—O23.9 (2)O1—C7—O2—C8176.85 (13)
O2—C8—C9—C52.6 (2)C6—C7—O2—C83.19 (19)
C10—C8—C9—C5176.97 (13)C9—C8—O2—C70.0 (2)
C4—C5—C9—C8176.28 (14)C10—C8—O2—C7179.62 (12)
C6—C5—C9—C81.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1i0.932.473.3157 (17)151
Symmetry code: (i) x, y+1/2, z1/2.
 

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