Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022458/rz2042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022458/rz2042Isup2.hkl
Contains datablock I

CCDC reference: 613804

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

No syntax errors found


No errors found in this datablock

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-(2-chlorobenzyl)-1H-isochromen-1-one top
Crystal data top
C16H11ClO2Z = 2
Mr = 270.70F(000) = 280
Triclinic, P1Dx = 1.432 Mg m3
Hall symbol: -P 1Melting point: 165(1) K
a = 7.2238 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1750 (4) ÅCell parameters from 3583 reflections
c = 10.7958 (6) Åθ = 0.0–0.0°
α = 83.978 (3)°µ = 0.30 mm1
β = 82.089 (4)°T = 273 K
γ = 89.509 (4)°Block, colourless
V = 627.98 (6) Å30.25 × 0.17 × 0.13 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2390 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 28.3°, θmin = 1.9°
φ and ω scansh = 99
11570 measured reflectionsk = 1010
3093 independent reflectionsl = 1414
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.0671P]
where P = (Fo2 + 2Fc2)/3
3093 reflections(Δ/σ)max = 0.010
172 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.15 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
Cl10.27638 (6)0.29342 (4)0.42698 (3)0.06232 (14)
C20.28111 (16)0.31132 (15)0.05412 (11)0.0394 (3)
C110.30848 (16)0.03535 (15)0.35473 (11)0.0397 (3)
C90.28896 (17)0.11072 (15)0.12486 (11)0.0409 (3)
C70.08768 (17)0.28876 (15)0.04495 (11)0.0399 (3)
C80.00972 (17)0.17490 (16)0.05586 (12)0.0438 (3)
C160.26582 (17)0.08623 (15)0.45395 (11)0.0405 (3)
C10.38030 (17)0.21580 (16)0.03551 (11)0.0423 (3)
H10.50910.22790.03070.051*
C150.21323 (19)0.05001 (17)0.57644 (12)0.0488 (3)
H150.18510.13450.64090.059*
C100.3711 (2)0.00200 (17)0.22044 (12)0.0490 (3)
H10A0.50630.00600.20330.059*
H10B0.33610.11430.21230.059*
C140.2029 (2)0.11090 (18)0.60222 (13)0.0533 (3)
H140.16840.13610.68420.064*
C120.29558 (19)0.19716 (16)0.38402 (13)0.0495 (3)
H120.32250.28220.31990.059*
C40.2682 (2)0.50856 (19)0.23478 (14)0.0591 (4)
H40.32860.58280.29840.071*
C60.0131 (2)0.37684 (18)0.13168 (13)0.0522 (3)
H60.14170.36200.12540.063*
C50.0775 (2)0.48494 (19)0.22574 (14)0.0603 (4)
H50.01040.54250.28360.072*
C30.3697 (2)0.42319 (17)0.15047 (13)0.0510 (3)
H30.49800.44000.15760.061*
C130.2440 (2)0.23501 (17)0.50561 (14)0.0544 (3)
H130.23690.34430.52240.065*
O10.09723 (12)0.09250 (11)0.13768 (8)0.0460 (2)
O20.17507 (13)0.14568 (15)0.07444 (10)0.0624 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0890 (3)0.03941 (18)0.0567 (2)0.00242 (16)0.00911 (18)0.00223 (15)
C20.0423 (6)0.0409 (6)0.0349 (6)0.0017 (5)0.0045 (5)0.0043 (5)
C110.0379 (6)0.0427 (6)0.0377 (6)0.0027 (5)0.0070 (5)0.0015 (5)
C90.0405 (6)0.0460 (6)0.0353 (6)0.0035 (5)0.0032 (5)0.0037 (5)
C70.0423 (6)0.0426 (6)0.0369 (6)0.0045 (5)0.0077 (5)0.0110 (5)
C80.0393 (6)0.0504 (7)0.0431 (6)0.0003 (5)0.0044 (5)0.0133 (5)
C160.0408 (6)0.0390 (6)0.0414 (6)0.0022 (5)0.0084 (5)0.0010 (5)
C10.0357 (6)0.0516 (7)0.0386 (6)0.0011 (5)0.0051 (5)0.0006 (5)
C150.0532 (8)0.0523 (7)0.0380 (6)0.0031 (6)0.0050 (5)0.0065 (5)
C100.0558 (8)0.0498 (7)0.0388 (6)0.0098 (6)0.0030 (5)0.0021 (5)
C140.0602 (8)0.0607 (8)0.0396 (7)0.0079 (7)0.0075 (6)0.0073 (6)
C120.0569 (8)0.0419 (7)0.0475 (7)0.0015 (6)0.0062 (6)0.0050 (5)
C40.0788 (11)0.0492 (8)0.0466 (7)0.0039 (7)0.0083 (7)0.0066 (6)
C60.0514 (8)0.0579 (8)0.0524 (7)0.0111 (6)0.0194 (6)0.0140 (6)
C50.0808 (11)0.0551 (8)0.0488 (8)0.0181 (7)0.0249 (7)0.0041 (6)
C30.0525 (8)0.0514 (8)0.0465 (7)0.0022 (6)0.0039 (6)0.0032 (6)
C130.0647 (9)0.0455 (7)0.0543 (8)0.0024 (6)0.0098 (7)0.0093 (6)
O10.0421 (5)0.0535 (5)0.0399 (5)0.0041 (4)0.0004 (4)0.0008 (4)
O20.0388 (5)0.0808 (7)0.0674 (7)0.0081 (5)0.0047 (5)0.0094 (6)
Geometric parameters (Å, º) top
C1—H10.9300C9—C101.4918 (17)
C2—C31.3982 (18)C9—O11.3806 (15)
C2—C71.3995 (17)C10—H10A0.9600
C2—C11.4430 (16)C10—H10B0.9600
C3—H30.9300C11—C101.5198 (17)
C4—H40.9300C11—C121.3914 (18)
C4—C31.376 (2)C11—C161.3861 (17)
C4—C51.381 (2)C11—CL12.7216 (13)
C5—H50.9300C12—C131.381 (2)
C6—C51.371 (2)C12—H120.9300
C6—H60.9300C13—H130.9300
C7—C61.4010 (17)C14—C131.380 (2)
C7—C81.4607 (18)C14—H140.9300
C8—O21.2054 (15)C15—C141.372 (2)
C8—O11.3729 (16)C15—H150.9300
C9—C11.3283 (17)C16—C151.3866 (18)
C1—C9—C10127.09 (12)C8—O1—C9122.47 (10)
C1—C9—O1121.65 (11)C9—C1—H1119.999
C2—C7—C6120.00 (12)C9—C1—C2120.46 (11)
C2—C7—C8120.10 (11)C9—C10—C11113.34 (10)
C2—C1—H1119.999C11—C16—C15122.23 (12)
C2—C3—H3119.999C11—C16—C11120.12 (10)
C3—C2—C7118.68 (11)C12—C11—C10120.47 (10)
C3—C2—C1123.05 (11)C13—C12—C11121.86 (13)
C3—C4—H4119.999C14—C13—C12120.10 (13)
C3—C4—C5120.59 (14)C14—C15—C16119.76 (12)
C4—C3—C2120.46 (13)C15—C16—C11122.23 (12)
C4—C3—H3119.999C15—C14—C13119.51 (12)
C4—C5—H5119.999C16—C11—C12116.54 (11)
C5—C4—H4119.999C16—C11—C10122.98 (11)
C5—C6—C7120.07 (13)H10A—C10—H10B108
C6—C7—C8119.90 (12)O1—C8—C7116.98 (10)
C6—C5—H5119.999O1—C9—C10111.25 (10)
C6—C5—C4120.20 (13)O2—C8—O1116.54 (12)
C7—C2—C1118.26 (11)O2—C8—C7126.48 (12)
C7—C8—O1—O2179.9 (2)C1—O1—C9—C10179.08 (19)
C15—C16—C11—Cl1179.75 (19)C11—C12—C10—Cl10.44 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···Cl10.972.593.0998 (14)113
C1—H1···O2i0.932.473.3333 (16)155
Symmetry code: (i) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds