3-(2-Chloro-6-fluoro­phen­yl)-1H-isochromen-1-one

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.

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

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Computing details

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

Crystal data

C15H8ClFO2	V = 607.5 (7) Å^3
Mr = 274.66	Z = 2
Triclinic, P1	F(000) = 280
Hall symbol: -P 1	Dx = 1.502 Mg m^−3
a = 7.228 (5) Å	Melting point: 514(2) K K
b = 7.467 (5) Å	Mo Kα radiation, λ = 0.71073 Å
c = 11.707 (8) Å	µ = 0.32 mm^−1
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

Bruker SMART CCD diffractometer	2068 independent reflections
Radiation source: fine-focus sealed tube	1745 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω and φ scan	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.673, Tmax = 0.940	k = −8→4
2887 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.187	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1019P)^2 + 0.507P] where P = (Fo^2 + 2Fc^2)/3
2068 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4282 (5)	−0.1920 (5)	0.4585 (3)	0.0506 (8)
H1A	0.5513	−0.1683	0.4500	0.061*
C2	0.3718 (5)	−0.3195 (5)	0.5519 (3)	0.0573 (9)
H2A	0.4578	−0.3821	0.6059	0.069*
C3	0.1895 (5)	−0.3549 (5)	0.5659 (3)	0.0550 (8)
H3A	0.1533	−0.4405	0.6296	0.066*
C4	0.0610 (5)	−0.2652 (4)	0.4867 (3)	0.0488 (8)
H4A	−0.0616	−0.2903	0.4962	0.059*
C5	0.1156 (4)	−0.1361 (4)	0.3917 (2)	0.0382 (6)
C6	0.2989 (4)	−0.0980 (4)	0.3763 (2)	0.0389 (7)
C7	0.3483 (4)	0.0379 (4)	0.2767 (3)	0.0458 (7)
H7A	0.4703	0.0648	0.2645	0.055*
C8	0.2199 (4)	0.1240 (4)	0.2030 (3)	0.0421 (7)
C9	−0.0229 (4)	−0.0412 (4)	0.3071 (3)	0.0436 (7)
C10	0.2450 (4)	0.2677 (4)	0.0971 (3)	0.0466 (8)
C11	0.2704 (6)	0.2195 (5)	−0.0144 (3)	0.0607 (9)
C12	0.2883 (6)	0.3429 (6)	−0.1170 (3)	0.0675 (10)
H12A	0.3066	0.3046	−0.1889	0.081*
C13	0.2782 (5)	0.5224 (6)	−0.1090 (3)	0.0623 (9)
H13A	0.2886	0.6085	−0.1776	0.075*
C14	0.2536 (5)	0.5833 (5)	−0.0058 (3)	0.0587 (9)
H14A	0.2467	0.7082	−0.0037	0.070*
C15	0.2386 (4)	0.4509 (5)	0.0992 (3)	0.0519 (8)
Cl1	0.20751 (16)	0.52405 (14)	0.23095 (9)	0.0721 (4)
F1	0.2736 (4)	0.0428 (3)	−0.02298 (19)	0.0836 (8)
O1	0.0372 (3)	0.0878 (3)	0.21635 (19)	0.0479 (6)
O2	−0.1826 (3)	−0.0640 (4)	0.3093 (2)	0.0641 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0441 (17)	0.0538 (19)	0.0514 (18)	−0.0102 (14)	−0.0080 (13)	0.0011 (15)
C2	0.066 (2)	0.058 (2)	0.0434 (18)	−0.0074 (17)	−0.0117 (15)	0.0032 (15)
C3	0.068 (2)	0.0549 (19)	0.0392 (17)	−0.0171 (16)	0.0010 (15)	0.0022 (14)
C4	0.0536 (18)	0.0504 (18)	0.0448 (17)	−0.0191 (15)	0.0046 (14)	−0.0089 (14)
C5	0.0421 (15)	0.0355 (14)	0.0379 (15)	−0.0093 (12)	0.0011 (11)	−0.0082 (12)
C6	0.0442 (16)	0.0333 (14)	0.0383 (15)	−0.0085 (12)	−0.0029 (12)	−0.0029 (12)
C7	0.0361 (15)	0.0469 (17)	0.0521 (18)	−0.0138 (13)	−0.0034 (13)	0.0031 (14)
C8	0.0400 (15)	0.0401 (15)	0.0451 (17)	−0.0109 (12)	−0.0036 (12)	−0.0010 (13)
C9	0.0402 (16)	0.0479 (17)	0.0444 (16)	−0.0150 (13)	0.0013 (12)	−0.0077 (13)
C10	0.0384 (16)	0.0429 (17)	0.0546 (19)	−0.0102 (13)	−0.0068 (13)	0.0051 (14)
C11	0.069 (2)	0.061 (2)	0.049 (2)	−0.0114 (17)	−0.0095 (16)	0.0007 (16)
C12	0.085 (3)	0.068 (2)	0.047 (2)	−0.012 (2)	−0.0100 (17)	−0.0010 (17)
C13	0.061 (2)	0.063 (2)	0.057 (2)	−0.0050 (17)	−0.0122 (16)	0.0040 (18)
C14	0.052 (2)	0.0416 (17)	0.078 (3)	−0.0085 (14)	−0.0088 (17)	0.0009 (17)
C15	0.0416 (17)	0.0470 (18)	0.063 (2)	−0.0092 (13)	−0.0020 (14)	−0.0007 (15)
Cl1	0.0910 (8)	0.0642 (6)	0.0659 (7)	−0.0161 (5)	0.0036 (5)	−0.0252 (5)
F1	0.148 (2)	0.0569 (13)	0.0583 (13)	−0.0381 (14)	−0.0004 (13)	−0.0236 (10)
O1	0.0388 (11)	0.0516 (13)	0.0496 (12)	−0.0123 (9)	−0.0077 (9)	0.0068 (10)
O2	0.0418 (13)	0.0877 (18)	0.0624 (15)	−0.0264 (12)	−0.0041 (10)	0.0024 (13)

Geometric parameters (Å, º)

C1—C2	1.380 (5)	C8—C10	1.490 (4)
C1—C6	1.405 (4)	C9—O2	1.194 (4)
C1—H1A	0.9300	C9—O1	1.377 (4)
C2—C3	1.377 (5)	C10—C15	1.365 (5)
C2—H2A	0.9300	C10—C11	1.406 (5)
C3—C4	1.371 (5)	C11—F1	1.339 (4)
C3—H3A	0.9300	C11—C12	1.372 (5)
C4—C5	1.394 (4)	C12—C13	1.350 (6)
C4—H4A	0.9300	C12—H12A	0.9300
C5—C6	1.391 (4)	C13—C14	1.356 (6)
C5—C9	1.469 (4)	C13—H13A	0.9300
C6—C7	1.447 (4)	C14—C15	1.426 (5)
C7—C8	1.323 (4)	C14—H14A	0.9300
C7—H7A	0.9300	C15—Cl1	1.715 (4)
C8—O1	1.382 (4)
C2—C1—C6	119.8 (3)	O1—C8—C10	110.3 (2)
C2—C1—H1A	120.1	O2—C9—O1	116.7 (3)
C6—C1—H1A	120.1	O2—C9—C5	126.6 (3)
C3—C2—C1	120.7 (3)	O1—C9—C5	116.7 (2)
C3—C2—H2A	119.7	C15—C10—C11	115.7 (3)
C1—C2—H2A	119.7	C15—C10—C8	124.1 (3)
C4—C3—C2	120.6 (3)	C11—C10—C8	120.1 (3)
C4—C3—H3A	119.7	F1—C11—C12	116.8 (3)
C2—C3—H3A	119.7	F1—C11—C10	118.8 (3)
C3—C4—C5	119.5 (3)	C12—C11—C10	124.4 (4)
C3—C4—H4A	120.3	C13—C12—C11	117.0 (4)
C5—C4—H4A	120.3	C13—C12—H12A	121.5
C6—C5—C4	120.8 (3)	C11—C12—H12A	121.5
C6—C5—C9	120.2 (3)	C12—C13—C14	123.3 (4)
C4—C5—C9	119.1 (3)	C12—C13—H13A	118.4
C5—C6—C1	118.7 (3)	C14—C13—H13A	118.4
C5—C6—C7	118.6 (3)	C13—C14—C15	118.3 (3)
C1—C6—C7	122.7 (3)	C13—C14—H14A	120.9
C8—C7—C6	120.0 (3)	C15—C14—H14A	120.9
C8—C7—H7A	120.0	C10—C15—C14	121.4 (3)
C6—C7—H7A	120.0	C10—C15—Cl1	119.3 (3)
C7—C8—O1	122.4 (3)	C14—C15—Cl1	119.3 (3)
C7—C8—C10	127.3 (3)	C9—O1—C8	122.1 (2)
C6—C1—C2—C3	−0.4 (5)	C7—C8—C10—C11	101.0 (4)
C1—C2—C3—C4	0.5 (6)	O1—C8—C10—C11	−78.7 (4)
C2—C3—C4—C5	−0.5 (5)	C15—C10—C11—F1	−178.5 (3)
C3—C4—C5—C6	0.3 (5)	C8—C10—C11—F1	−0.7 (5)
C3—C4—C5—C9	179.8 (3)	C15—C10—C11—C12	0.0 (5)
C4—C5—C6—C1	−0.2 (4)	C8—C10—C11—C12	177.7 (3)
C9—C5—C6—C1	−179.6 (3)	F1—C11—C12—C13	177.6 (4)
C4—C5—C6—C7	−179.7 (3)	C10—C11—C12—C13	−0.9 (6)
C9—C5—C6—C7	0.8 (4)	C11—C12—C13—C14	0.7 (6)
C2—C1—C6—C5	0.2 (5)	C12—C13—C14—C15	0.3 (6)
C2—C1—C6—C7	179.7 (3)	C11—C10—C15—C14	1.1 (5)
C5—C6—C7—C8	0.5 (5)	C8—C10—C15—C14	−176.6 (3)
C1—C6—C7—C8	−179.0 (3)	C11—C10—C15—Cl1	179.9 (2)
C6—C7—C8—O1	−0.8 (5)	C8—C10—C15—Cl1	2.2 (4)
C6—C7—C8—C10	179.6 (3)	C13—C14—C15—C10	−1.2 (5)
C6—C5—C9—O2	178.5 (3)	C13—C14—C15—Cl1	180.0 (3)
C4—C5—C9—O2	−1.0 (5)	O2—C9—O1—C8	−178.7 (3)
C6—C5—C9—O1	−1.8 (4)	C5—C9—O1—C8	1.6 (4)
C4—C5—C9—O1	178.7 (3)	C7—C8—O1—C9	−0.3 (5)
C7—C8—C10—C15	−81.4 (5)	C10—C8—O1—C9	179.4 (3)
O1—C8—C10—C15	98.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2^i	0.93	2.53	3.342 (5)	146
C7—H7A···O2^i	0.93	2.59	3.382 (4)	144
C14—H14A···F1^ii	0.93	2.51	3.426 (5)	170

Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.