3-(2-Chloro­benz­yl)isocoumarin

In the title compound, C₁₆H₁₁ClO₂, an unnaturally occurring isocoumarin, the benzene ring is nearly perpendicular to the planar isocoumarin ring system. The crystal packing is stabilized by intra- and inter­molecular C—H...Cl and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.032
• wR factor = 0.100
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

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Computing details

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-(2-chlorobenzyl)-1H-isochromen-1-one

Crystal data

C16H11ClO2	Z = 2
Mr = 270.70	F(000) = 280
Triclinic, P1	Dx = 1.432 Mg m^−3
Hall symbol: -P 1	Melting point: 165(1) K
a = 7.2238 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1750 (4) Å	Cell parameters from 3583 reflections
c = 10.7958 (6) Å	θ = 0.0–0.0°
α = 83.978 (3)°	µ = 0.30 mm^−1
β = 82.089 (4)°	T = 273 K
γ = 89.509 (4)°	Block, colourless
V = 627.98 (6) Å^3	0.25 × 0.17 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2390 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −9→9
11570 measured reflections	k = −10→10
3093 independent reflections	l = −14→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 0.0671P] where P = (Fo^2 + 2Fc^2)/3
3093 reflections	(Δ/σ)max = 0.010
172 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.15 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	0.27638 (6)	−0.29342 (4)	0.42698 (3)	0.06232 (14)
C2	0.28111 (16)	0.31132 (15)	−0.05412 (11)	0.0394 (3)
C11	0.30848 (16)	0.03535 (15)	0.35473 (11)	0.0397 (3)
C9	0.28896 (17)	0.11072 (15)	0.12486 (11)	0.0409 (3)
C7	0.08768 (17)	0.28876 (15)	−0.04495 (11)	0.0399 (3)
C8	−0.00972 (17)	0.17490 (16)	0.05586 (12)	0.0438 (3)
C16	0.26582 (17)	−0.08623 (15)	0.45395 (11)	0.0405 (3)
C1	0.38030 (17)	0.21580 (16)	0.03551 (11)	0.0423 (3)
H1	0.5091	0.2279	0.0307	0.051*
C15	0.21323 (19)	−0.05001 (17)	0.57644 (12)	0.0488 (3)
H15	0.1851	−0.1345	0.6409	0.059*
C10	0.3711 (2)	−0.00200 (17)	0.22044 (12)	0.0490 (3)
H10A	0.5063	0.0060	0.2033	0.059*
H10B	0.3361	−0.1143	0.2123	0.059*
C14	0.2029 (2)	0.11090 (18)	0.60222 (13)	0.0533 (3)
H14	0.1684	0.1361	0.6842	0.064*
C12	0.29558 (19)	0.19716 (16)	0.38402 (13)	0.0495 (3)
H12	0.3225	0.2822	0.3199	0.059*
C4	0.2682 (2)	0.50856 (19)	−0.23478 (14)	0.0591 (4)
H4	0.3286	0.5828	−0.2984	0.071*
C6	−0.0131 (2)	0.37684 (18)	−0.13168 (13)	0.0522 (3)
H6	−0.1417	0.3620	−0.1254	0.063*
C5	0.0775 (2)	0.48494 (19)	−0.22574 (14)	0.0603 (4)
H5	0.0104	0.5425	−0.2836	0.072*
C3	0.3697 (2)	0.42319 (17)	−0.15047 (13)	0.0510 (3)
H3	0.4980	0.4400	−0.1576	0.061*
C13	0.2440 (2)	0.23501 (17)	0.50561 (14)	0.0544 (3)
H13	0.2369	0.3443	0.5224	0.065*
O1	0.09723 (12)	0.09250 (11)	0.13768 (8)	0.0460 (2)
O2	−0.17507 (13)	0.14568 (15)	0.07444 (10)	0.0624 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0890 (3)	0.03941 (18)	0.0567 (2)	0.00242 (16)	−0.00911 (18)	0.00223 (15)
C2	0.0423 (6)	0.0409 (6)	0.0349 (6)	0.0017 (5)	−0.0045 (5)	−0.0043 (5)
C11	0.0379 (6)	0.0427 (6)	0.0377 (6)	0.0027 (5)	−0.0070 (5)	0.0015 (5)
C9	0.0405 (6)	0.0460 (6)	0.0353 (6)	0.0035 (5)	−0.0032 (5)	−0.0037 (5)
C7	0.0423 (6)	0.0426 (6)	0.0369 (6)	0.0045 (5)	−0.0077 (5)	−0.0110 (5)
C8	0.0393 (6)	0.0504 (7)	0.0431 (6)	−0.0003 (5)	−0.0044 (5)	−0.0133 (5)
C16	0.0408 (6)	0.0390 (6)	0.0414 (6)	0.0022 (5)	−0.0084 (5)	0.0010 (5)
C1	0.0357 (6)	0.0516 (7)	0.0386 (6)	0.0011 (5)	−0.0051 (5)	−0.0006 (5)
C15	0.0532 (8)	0.0523 (7)	0.0380 (6)	0.0031 (6)	−0.0050 (5)	0.0065 (5)
C10	0.0558 (8)	0.0498 (7)	0.0388 (6)	0.0098 (6)	−0.0030 (5)	0.0021 (5)
C14	0.0602 (8)	0.0607 (8)	0.0396 (7)	0.0079 (7)	−0.0075 (6)	−0.0073 (6)
C12	0.0569 (8)	0.0419 (7)	0.0475 (7)	−0.0015 (6)	−0.0062 (6)	0.0050 (5)
C4	0.0788 (11)	0.0492 (8)	0.0466 (7)	0.0039 (7)	−0.0083 (7)	0.0066 (6)
C6	0.0514 (8)	0.0579 (8)	0.0524 (7)	0.0111 (6)	−0.0194 (6)	−0.0140 (6)
C5	0.0808 (11)	0.0551 (8)	0.0488 (8)	0.0181 (7)	−0.0249 (7)	−0.0041 (6)
C3	0.0525 (8)	0.0514 (8)	0.0465 (7)	−0.0022 (6)	−0.0039 (6)	0.0032 (6)
C13	0.0647 (9)	0.0455 (7)	0.0543 (8)	0.0024 (6)	−0.0098 (7)	−0.0093 (6)
O1	0.0421 (5)	0.0535 (5)	0.0399 (5)	−0.0041 (4)	−0.0004 (4)	0.0008 (4)
O2	0.0388 (5)	0.0808 (7)	0.0674 (7)	−0.0081 (5)	−0.0047 (5)	−0.0094 (6)

Geometric parameters (Å, º)

C1—H1	0.9300	C9—C10	1.4918 (17)
C2—C3	1.3982 (18)	C9—O1	1.3806 (15)
C2—C7	1.3995 (17)	C10—H10A	0.9600
C2—C1	1.4430 (16)	C10—H10B	0.9600
C3—H3	0.9300	C11—C10	1.5198 (17)
C4—H4	0.9300	C11—C12	1.3914 (18)
C4—C3	1.376 (2)	C11—C16	1.3861 (17)
C4—C5	1.381 (2)	C11—CL1	2.7216 (13)
C5—H5	0.9300	C12—C13	1.381 (2)
C6—C5	1.371 (2)	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—C6	1.4010 (17)	C14—C13	1.380 (2)
C7—C8	1.4607 (18)	C14—H14	0.9300
C8—O2	1.2054 (15)	C15—C14	1.372 (2)
C8—O1	1.3729 (16)	C15—H15	0.9300
C9—C1	1.3283 (17)	C16—C15	1.3866 (18)
C1—C9—C10	127.09 (12)	C8—O1—C9	122.47 (10)
C1—C9—O1	121.65 (11)	C9—C1—H1	119.999
C2—C7—C6	120.00 (12)	C9—C1—C2	120.46 (11)
C2—C7—C8	120.10 (11)	C9—C10—C11	113.34 (10)
C2—C1—H1	119.999	C11—C16—C15	122.23 (12)
C2—C3—H3	119.999	C11—C16—C11	120.12 (10)
C3—C2—C7	118.68 (11)	C12—C11—C10	120.47 (10)
C3—C2—C1	123.05 (11)	C13—C12—C11	121.86 (13)
C3—C4—H4	119.999	C14—C13—C12	120.10 (13)
C3—C4—C5	120.59 (14)	C14—C15—C16	119.76 (12)
C4—C3—C2	120.46 (13)	C15—C16—C11	122.23 (12)
C4—C3—H3	119.999	C15—C14—C13	119.51 (12)
C4—C5—H5	119.999	C16—C11—C12	116.54 (11)
C5—C4—H4	119.999	C16—C11—C10	122.98 (11)
C5—C6—C7	120.07 (13)	H10A—C10—H10B	108
C6—C7—C8	119.90 (12)	O1—C8—C7	116.98 (10)
C6—C5—H5	119.999	O1—C9—C10	111.25 (10)
C6—C5—C4	120.20 (13)	O2—C8—O1	116.54 (12)
C7—C2—C1	118.26 (11)	O2—C8—C7	126.48 (12)
C7—C8—O1—O2	−179.9 (2)	C1—O1—C9—C10	−179.08 (19)
C15—C16—C11—Cl1	−179.75 (19)	C11—C12—C10—Cl1	−0.44 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···Cl1	0.97	2.59	3.0998 (14)	113
C1—H1···O2^i	0.93	2.47	3.3333 (16)	155

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