3-(4-Chloro­phen­yl)isocoumarin

Mol­ecules of the title compound, C₁₅H₉ClO₂, are essentially planar. They are connected by C—H...O hydrogen bonds into chains running along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.091
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C2      ..       6.19 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

3-(4-Chlorophenyl)isocoumarin

Crystal data

C15H9ClO2	Z = 2
Mr = 256.67	F(000) = 264
Triclinic, P1	Dx = 1.433 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0616 (8) Å	Cell parameters from 7247 reflections
b = 7.2258 (8) Å	θ = 3.6–26.1°
c = 13.0949 (14) Å	µ = 0.31 mm^−1
α = 96.211 (8)°	T = 173 K
β = 104.611 (9)°	Plate, light yellow
γ = 109.701 (9)°	0.32 × 0.27 × 0.13 mm
V = 594.87 (13) Å^3

Data collection

Stoe IPDSII two-circle diffractometer	2406 independent reflections
Radiation source: fine-focus sealed tube	2052 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 26.3°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −8→8
Tmin = 0.909, Tmax = 0.981	k = −9→9
7741 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0517P)^2 + 0.0785P] where P = (Fo^2 + 2Fc^2)/3
2406 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.27 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 > 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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.25415 (7)	1.07493 (6)	0.93710 (3)	0.05134 (15)
O1	0.25237 (13)	0.53626 (12)	0.49014 (7)	0.0288 (2)
O2	0.27623 (15)	0.26925 (13)	0.40324 (8)	0.0374 (2)
C2	0.26261 (18)	0.43137 (17)	0.39855 (11)	0.0284 (3)
C3	0.25370 (18)	0.52358 (17)	0.30390 (11)	0.0278 (3)
C4	0.2597 (2)	0.42292 (19)	0.20814 (12)	0.0363 (3)
H4	0.2751	0.2970	0.2051	0.044*
C5	0.2434 (2)	0.5066 (2)	0.11769 (12)	0.0418 (3)
H5	0.2480	0.4387	0.0526	0.050*
C6	0.2199 (2)	0.6927 (2)	0.12257 (12)	0.0394 (3)
H6	0.2069	0.7493	0.0602	0.047*
C7	0.2155 (2)	0.79405 (19)	0.21670 (11)	0.0328 (3)
H7	0.2004	0.9201	0.2188	0.039*
C8	0.23311 (18)	0.71198 (17)	0.30992 (10)	0.0266 (3)
C9	0.23342 (18)	0.81307 (17)	0.41085 (10)	0.0275 (3)
H9	0.2255	0.9423	0.4166	0.033*
C10	0.24476 (18)	0.72726 (17)	0.49692 (10)	0.0255 (3)
C11	0.25097 (18)	0.81282 (17)	0.60560 (10)	0.0266 (3)
C12	0.2322 (2)	1.00081 (19)	0.62652 (10)	0.0300 (3)
H12	0.2182	1.0731	0.5705	0.036*
C13	0.2340 (2)	1.08046 (19)	0.72787 (11)	0.0337 (3)
H13	0.2207	1.2066	0.7414	0.040*
C14	0.2553 (2)	0.9742 (2)	0.80978 (11)	0.0346 (3)
C15	0.2764 (2)	0.7903 (2)	0.79211 (11)	0.0363 (3)
H15	0.2922	0.7199	0.8489	0.044*
C16	0.2741 (2)	0.71053 (19)	0.69019 (11)	0.0323 (3)
H16	0.2883	0.5847	0.6776	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0705 (3)	0.0584 (3)	0.0354 (2)	0.0346 (2)	0.01990 (18)	0.00911 (16)
O1	0.0318 (4)	0.0167 (4)	0.0373 (5)	0.0098 (3)	0.0071 (4)	0.0092 (3)
O2	0.0405 (5)	0.0193 (4)	0.0567 (6)	0.0157 (4)	0.0145 (4)	0.0122 (4)
C2	0.0216 (5)	0.0187 (5)	0.0420 (7)	0.0066 (4)	0.0067 (5)	0.0060 (5)
C3	0.0218 (5)	0.0195 (5)	0.0395 (7)	0.0072 (4)	0.0061 (5)	0.0060 (5)
C4	0.0346 (7)	0.0250 (6)	0.0459 (8)	0.0118 (5)	0.0092 (6)	0.0002 (5)
C5	0.0450 (8)	0.0399 (8)	0.0373 (7)	0.0162 (6)	0.0105 (6)	−0.0003 (6)
C6	0.0427 (8)	0.0401 (7)	0.0345 (7)	0.0157 (6)	0.0089 (6)	0.0108 (6)
C7	0.0362 (7)	0.0269 (6)	0.0364 (7)	0.0140 (5)	0.0089 (5)	0.0097 (5)
C8	0.0223 (5)	0.0208 (6)	0.0342 (6)	0.0077 (4)	0.0053 (5)	0.0058 (5)
C9	0.0286 (6)	0.0176 (5)	0.0367 (7)	0.0105 (4)	0.0075 (5)	0.0069 (5)
C10	0.0218 (5)	0.0171 (5)	0.0356 (6)	0.0072 (4)	0.0053 (5)	0.0063 (4)
C11	0.0208 (5)	0.0222 (6)	0.0340 (6)	0.0064 (4)	0.0055 (5)	0.0077 (5)
C12	0.0299 (6)	0.0261 (6)	0.0340 (6)	0.0119 (5)	0.0073 (5)	0.0082 (5)
C13	0.0329 (7)	0.0292 (6)	0.0381 (7)	0.0136 (5)	0.0081 (5)	0.0046 (5)
C14	0.0319 (6)	0.0385 (7)	0.0323 (6)	0.0134 (5)	0.0094 (5)	0.0045 (5)
C15	0.0383 (7)	0.0375 (7)	0.0362 (7)	0.0159 (6)	0.0111 (6)	0.0152 (5)
C16	0.0330 (6)	0.0261 (6)	0.0391 (7)	0.0121 (5)	0.0102 (5)	0.0112 (5)

Geometric parameters (Å, º)

Cl1—C14	1.7487 (14)	C8—C9	1.4383 (18)
O1—C2	1.3791 (16)	C9—C10	1.3418 (18)
O1—C10	1.3933 (14)	C9—H9	0.9500
O2—C2	1.2140 (15)	C10—C11	1.4729 (18)
C2—C3	1.4670 (18)	C11—C16	1.4026 (17)
C3—C4	1.3978 (19)	C11—C12	1.4132 (17)
C3—C8	1.4130 (16)	C12—C13	1.3835 (19)
C4—C5	1.384 (2)	C12—H12	0.9500
C4—H4	0.9500	C13—C14	1.392 (2)
C5—C6	1.406 (2)	C13—H13	0.9500
C5—H5	0.9500	C14—C15	1.388 (2)
C6—C7	1.377 (2)	C15—C16	1.389 (2)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.4098 (17)	C16—H16	0.9500
C7—H7	0.9500
C2—O1—C10	122.60 (10)	C10—C9—H9	119.6
O2—C2—O1	116.82 (12)	C8—C9—H9	119.6
O2—C2—C3	125.72 (12)	C9—C10—O1	120.80 (11)
O1—C2—C3	117.46 (10)	C9—C10—C11	127.22 (11)
C4—C3—C8	120.64 (12)	O1—C10—C11	111.97 (11)
C4—C3—C2	120.10 (11)	C16—C11—C12	118.47 (12)
C8—C3—C2	119.24 (12)	C16—C11—C10	121.28 (11)
C5—C4—C3	120.04 (12)	C12—C11—C10	120.25 (11)
C5—C4—H4	120.0	C13—C12—C11	120.59 (12)
C3—C4—H4	120.0	C13—C12—H12	119.7
C4—C5—C6	119.68 (13)	C11—C12—H12	119.7
C4—C5—H5	120.2	C12—C13—C14	119.46 (12)
C6—C5—H5	120.2	C12—C13—H13	120.3
C7—C6—C5	120.80 (13)	C14—C13—H13	120.3
C7—C6—H6	119.6	C15—C14—C13	121.32 (13)
C5—C6—H6	119.6	C15—C14—Cl1	119.62 (11)
C6—C7—C8	120.42 (12)	C13—C14—Cl1	119.06 (10)
C6—C7—H7	119.8	C14—C15—C16	119.05 (13)
C8—C7—H7	119.8	C14—C15—H15	120.5
C7—C8—C3	118.41 (12)	C16—C15—H15	120.5
C7—C8—C9	122.73 (11)	C15—C16—C11	121.09 (12)
C3—C8—C9	118.86 (11)	C15—C16—H16	119.5
C10—C9—C8	120.85 (10)	C11—C16—H16	119.5
C10—O1—C2—O2	177.43 (10)	C8—C9—C10—O1	−1.26 (18)
C10—O1—C2—C3	−3.25 (15)	C8—C9—C10—C11	178.67 (10)
O2—C2—C3—C4	0.34 (19)	C2—O1—C10—C9	4.31 (17)
O1—C2—C3—C4	−178.91 (10)	C2—O1—C10—C11	−175.63 (9)
O2—C2—C3—C8	178.60 (12)	C9—C10—C11—C16	−176.62 (12)
O1—C2—C3—C8	−0.65 (16)	O1—C10—C11—C16	3.32 (16)
C8—C3—C4—C5	−0.65 (19)	C9—C10—C11—C12	3.79 (19)
C2—C3—C4—C5	177.59 (12)	O1—C10—C11—C12	−176.27 (10)
C3—C4—C5—C6	−0.2 (2)	C16—C11—C12—C13	−0.79 (18)
C4—C5—C6—C7	0.8 (2)	C10—C11—C12—C13	178.81 (11)
C5—C6—C7—C8	−0.4 (2)	C11—C12—C13—C14	0.3 (2)
C6—C7—C8—C3	−0.47 (19)	C12—C13—C14—C15	0.5 (2)
C6—C7—C8—C9	178.80 (12)	C12—C13—C14—Cl1	−179.22 (10)
C4—C3—C8—C7	1.00 (18)	C13—C14—C15—C16	−0.6 (2)
C2—C3—C8—C7	−177.25 (10)	Cl1—C14—C15—C16	179.08 (10)
C4—C3—C8—C9	−178.30 (11)	C14—C15—C16—C11	0.0 (2)
C2—C3—C8—C9	3.45 (17)	C12—C11—C16—C15	0.64 (19)
C7—C8—C9—C10	178.17 (11)	C10—C11—C16—C15	−178.95 (11)
C3—C8—C9—C10	−2.56 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2^i	0.95	2.30	3.2220 (14)	163

Symmetry code: (i) x, y+1, z.