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The title compound, C15H8ClFO2, is a chemically synthesized isocoumarin. The isocoumarin and benzene ring systems are approximately perpendicular to each other. The crystal packing is stabilized by C—H...O and C—H...F inter­­actions to form one-dimensional chains parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043777/rz2083sup1.cif
Contains datablocks wy1575wm, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043777/rz2083Isup2.hkl
Contains datablock I

CCDC reference: 628077

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.062
  • wR factor = 0.187
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.673 0.940 Tmin(prime) and Tmax expected: 0.901 0.938 RR(prime) = 0.746 Please check that your absorption correction is appropriate. PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.74 PLAT230_ALERT_2_B Hirshfeld Test Diff for Cl1 - C15 .. 8.13 su PLAT230_ALERT_2_B Hirshfeld Test Diff for F1 - C11 .. 9.48 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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, 2000); cell refinement: SAINT (Bruker, 2000); 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: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(2-Chloro-6-fluorophenyl)-1H-isochromen-1-one top
Crystal data top
C15H8ClFO2V = 607.5 (7) Å3
Mr = 274.66Z = 2
Triclinic, P1F(000) = 280
Hall symbol: -P 1Dx = 1.502 Mg m3
a = 7.228 (5) ÅMelting point: 514(2) K K
b = 7.467 (5) ÅMo Kα radiation, λ = 0.71073 Å
c = 11.707 (8) ŵ = 0.32 mm1
α = 78.608 (13)°T = 293 K
β = 83.984 (12)°Block, colourless
γ = 79.531 (12)°0.32 × 0.26 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer
2068 independent reflections
Radiation source: fine-focus sealed tube1745 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω and φ scanθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 88
Tmin = 0.673, Tmax = 0.940k = 84
2887 measured reflectionsl = 1313
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1019P)2 + 0.507P]
where P = (Fo2 + 2Fc2)/3
2068 reflections(Δ/σ)max = 0.001
172 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = 0.33 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 > 2σ(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
C10.4282 (5)0.1920 (5)0.4585 (3)0.0506 (8)
H1A0.55130.16830.45000.061*
C20.3718 (5)0.3195 (5)0.5519 (3)0.0573 (9)
H2A0.45780.38210.60590.069*
C30.1895 (5)0.3549 (5)0.5659 (3)0.0550 (8)
H3A0.15330.44050.62960.066*
C40.0610 (5)0.2652 (4)0.4867 (3)0.0488 (8)
H4A0.06160.29030.49620.059*
C50.1156 (4)0.1361 (4)0.3917 (2)0.0382 (6)
C60.2989 (4)0.0980 (4)0.3763 (2)0.0389 (7)
C70.3483 (4)0.0379 (4)0.2767 (3)0.0458 (7)
H7A0.47030.06480.26450.055*
C80.2199 (4)0.1240 (4)0.2030 (3)0.0421 (7)
C90.0229 (4)0.0412 (4)0.3071 (3)0.0436 (7)
C100.2450 (4)0.2677 (4)0.0971 (3)0.0466 (8)
C110.2704 (6)0.2195 (5)0.0144 (3)0.0607 (9)
C120.2883 (6)0.3429 (6)0.1170 (3)0.0675 (10)
H12A0.30660.30460.18890.081*
C130.2782 (5)0.5224 (6)0.1090 (3)0.0623 (9)
H13A0.28860.60850.17760.075*
C140.2536 (5)0.5833 (5)0.0058 (3)0.0587 (9)
H14A0.24670.70820.00370.070*
C150.2386 (4)0.4509 (5)0.0992 (3)0.0519 (8)
Cl10.20751 (16)0.52405 (14)0.23095 (9)0.0721 (4)
F10.2736 (4)0.0428 (3)0.02298 (19)0.0836 (8)
O10.0372 (3)0.0878 (3)0.21635 (19)0.0479 (6)
O20.1826 (3)0.0640 (4)0.3093 (2)0.0641 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0441 (17)0.0538 (19)0.0514 (18)0.0102 (14)0.0080 (13)0.0011 (15)
C20.066 (2)0.058 (2)0.0434 (18)0.0074 (17)0.0117 (15)0.0032 (15)
C30.068 (2)0.0549 (19)0.0392 (17)0.0171 (16)0.0010 (15)0.0022 (14)
C40.0536 (18)0.0504 (18)0.0448 (17)0.0191 (15)0.0046 (14)0.0089 (14)
C50.0421 (15)0.0355 (14)0.0379 (15)0.0093 (12)0.0011 (11)0.0082 (12)
C60.0442 (16)0.0333 (14)0.0383 (15)0.0085 (12)0.0029 (12)0.0029 (12)
C70.0361 (15)0.0469 (17)0.0521 (18)0.0138 (13)0.0034 (13)0.0031 (14)
C80.0400 (15)0.0401 (15)0.0451 (17)0.0109 (12)0.0036 (12)0.0010 (13)
C90.0402 (16)0.0479 (17)0.0444 (16)0.0150 (13)0.0013 (12)0.0077 (13)
C100.0384 (16)0.0429 (17)0.0546 (19)0.0102 (13)0.0068 (13)0.0051 (14)
C110.069 (2)0.061 (2)0.049 (2)0.0114 (17)0.0095 (16)0.0007 (16)
C120.085 (3)0.068 (2)0.047 (2)0.012 (2)0.0100 (17)0.0010 (17)
C130.061 (2)0.063 (2)0.057 (2)0.0050 (17)0.0122 (16)0.0040 (18)
C140.052 (2)0.0416 (17)0.078 (3)0.0085 (14)0.0088 (17)0.0009 (17)
C150.0416 (17)0.0470 (18)0.063 (2)0.0092 (13)0.0020 (14)0.0007 (15)
Cl10.0910 (8)0.0642 (6)0.0659 (7)0.0161 (5)0.0036 (5)0.0252 (5)
F10.148 (2)0.0569 (13)0.0583 (13)0.0381 (14)0.0004 (13)0.0236 (10)
O10.0388 (11)0.0516 (13)0.0496 (12)0.0123 (9)0.0077 (9)0.0068 (10)
O20.0418 (13)0.0877 (18)0.0624 (15)0.0264 (12)0.0041 (10)0.0024 (13)
Geometric parameters (Å, º) top
C1—C21.380 (5)C8—C101.490 (4)
C1—C61.405 (4)C9—O21.194 (4)
C1—H1A0.9300C9—O11.377 (4)
C2—C31.377 (5)C10—C151.365 (5)
C2—H2A0.9300C10—C111.406 (5)
C3—C41.371 (5)C11—F11.339 (4)
C3—H3A0.9300C11—C121.372 (5)
C4—C51.394 (4)C12—C131.350 (6)
C4—H4A0.9300C12—H12A0.9300
C5—C61.391 (4)C13—C141.356 (6)
C5—C91.469 (4)C13—H13A0.9300
C6—C71.447 (4)C14—C151.426 (5)
C7—C81.323 (4)C14—H14A0.9300
C7—H7A0.9300C15—Cl11.715 (4)
C8—O11.382 (4)
C2—C1—C6119.8 (3)O1—C8—C10110.3 (2)
C2—C1—H1A120.1O2—C9—O1116.7 (3)
C6—C1—H1A120.1O2—C9—C5126.6 (3)
C3—C2—C1120.7 (3)O1—C9—C5116.7 (2)
C3—C2—H2A119.7C15—C10—C11115.7 (3)
C1—C2—H2A119.7C15—C10—C8124.1 (3)
C4—C3—C2120.6 (3)C11—C10—C8120.1 (3)
C4—C3—H3A119.7F1—C11—C12116.8 (3)
C2—C3—H3A119.7F1—C11—C10118.8 (3)
C3—C4—C5119.5 (3)C12—C11—C10124.4 (4)
C3—C4—H4A120.3C13—C12—C11117.0 (4)
C5—C4—H4A120.3C13—C12—H12A121.5
C6—C5—C4120.8 (3)C11—C12—H12A121.5
C6—C5—C9120.2 (3)C12—C13—C14123.3 (4)
C4—C5—C9119.1 (3)C12—C13—H13A118.4
C5—C6—C1118.7 (3)C14—C13—H13A118.4
C5—C6—C7118.6 (3)C13—C14—C15118.3 (3)
C1—C6—C7122.7 (3)C13—C14—H14A120.9
C8—C7—C6120.0 (3)C15—C14—H14A120.9
C8—C7—H7A120.0C10—C15—C14121.4 (3)
C6—C7—H7A120.0C10—C15—Cl1119.3 (3)
C7—C8—O1122.4 (3)C14—C15—Cl1119.3 (3)
C7—C8—C10127.3 (3)C9—O1—C8122.1 (2)
C6—C1—C2—C30.4 (5)C7—C8—C10—C11101.0 (4)
C1—C2—C3—C40.5 (6)O1—C8—C10—C1178.7 (4)
C2—C3—C4—C50.5 (5)C15—C10—C11—F1178.5 (3)
C3—C4—C5—C60.3 (5)C8—C10—C11—F10.7 (5)
C3—C4—C5—C9179.8 (3)C15—C10—C11—C120.0 (5)
C4—C5—C6—C10.2 (4)C8—C10—C11—C12177.7 (3)
C9—C5—C6—C1179.6 (3)F1—C11—C12—C13177.6 (4)
C4—C5—C6—C7179.7 (3)C10—C11—C12—C130.9 (6)
C9—C5—C6—C70.8 (4)C11—C12—C13—C140.7 (6)
C2—C1—C6—C50.2 (5)C12—C13—C14—C150.3 (6)
C2—C1—C6—C7179.7 (3)C11—C10—C15—C141.1 (5)
C5—C6—C7—C80.5 (5)C8—C10—C15—C14176.6 (3)
C1—C6—C7—C8179.0 (3)C11—C10—C15—Cl1179.9 (2)
C6—C7—C8—O10.8 (5)C8—C10—C15—Cl12.2 (4)
C6—C7—C8—C10179.6 (3)C13—C14—C15—C101.2 (5)
C6—C5—C9—O2178.5 (3)C13—C14—C15—Cl1180.0 (3)
C4—C5—C9—O21.0 (5)O2—C9—O1—C8178.7 (3)
C6—C5—C9—O11.8 (4)C5—C9—O1—C81.6 (4)
C4—C5—C9—O1178.7 (3)C7—C8—O1—C90.3 (5)
C7—C8—C10—C1581.4 (5)C10—C8—O1—C9179.4 (3)
O1—C8—C10—C1598.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O2i0.932.533.342 (5)146
C7—H7A···O2i0.932.593.382 (4)144
C14—H14A···F1ii0.932.513.426 (5)170
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.
 

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