Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049409/dn2237sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049409/dn2237Isup2.hkl |
CCDC reference: 667367
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.087
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.13 PLAT230_ALERT_2_C Hirshfeld Test Diff for O13 - C111 .. 5.64 su
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C102 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C202 = ... S
0 ALERT level A = In general: serious problem 0 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 0 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
Hydrogen atoms were located in difference syntheses, refined at idealized positions riding on the C (C–H = 0.95–0.99 Å) atoms with isotropic displacement parameters Uiso(H) = 1.2U(Ceq) and 1.5(methyl-C). Methyl H atoms were refined on the basis of rigid groups allowed to rotate but not tip.
Isobenzofuran-1-ones (phtalides) are an important class of natural products and are part of the structure of several alkaloids like bicuculline (Ogawa et al., 1996). Furthermore, phtalides are intermediates towards the synthesis of several alkaloids and isocoumarins and exhibit a wide range of biological activities. Thus, 3-n-butylphtalide a constituent of celery seed oil, exhibits anticonvulsant, asthmatic, and antitumor properties (Xiong & Li, 2007); phenolphthalein a well known pH indicator, and its derivatives like 4-Fluoro-3,3-bis-(4-hydroxy-phenyl)-3H-isobenzofuran-1-one are low micromolar inhibitor of the enzyme Thymidylate Synthase, an important target for anticancer chemotherapy (Calo et al., 2004). Diaporthelactone (3-dihydro-4-methoxy-7-methyl-3-oxo-5-isobenzo furan-carboxyaldehyde) and 7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one isolated from the culture of Diaporthe sp., show cytotoxic activity against KB and Raji cell lines (Lin et al., 2005). Three isocoumarins and a benzofuran derivative Pyrenulafuran were isolated from the cultured lichen mycobionts of Pyrenula sp. (Takenaka et al., 2004). Naphthalenone and phthalide metabolites from Lachnum papyraceum possesses weak antimicrobial and phytotoxic activities and weak cytotoxicity (Shan et al., 1997)·The title compound was prepared as an intermediate towards isocoumarins and dihydroisocoumarins.
For related literature, see: Calo et al. (2004); Lin et al. (2005); Ogawa et al. (1996); Shan et al. (1997); Takenaka et al. (2004); Xiong & Li (2007).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL (Bruker, 2002); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002).
C11H9Cl3O4 | F(000) = 1264 |
Mr = 311.53 | Dx = 1.626 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 962 reflections |
a = 12.478 (3) Å | θ = 2.6–28.3° |
b = 17.100 (4) Å | µ = 0.72 mm−1 |
c = 12.084 (3) Å | T = 153 K |
β = 99.129 (4)° | Prism, colourless |
V = 2545.8 (11) Å3 | 0.51 × 0.40 × 0.28 mm |
Z = 8 |
Bruker SMART APEX diffractometer | 6059 independent reflections |
Radiation source: sealed tube | 5282 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 27.9°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −16→16 |
Tmin = 0.710, Tmax = 0.824 | k = −22→22 |
21365 measured reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.9873P] where P = (Fo2 + 2Fc2)/3 |
6059 reflections | (Δ/σ)max = 0.001 |
329 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C11H9Cl3O4 | V = 2545.8 (11) Å3 |
Mr = 311.53 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.478 (3) Å | µ = 0.72 mm−1 |
b = 17.100 (4) Å | T = 153 K |
c = 12.084 (3) Å | 0.51 × 0.40 × 0.28 mm |
β = 99.129 (4)° |
Bruker SMART APEX diffractometer | 6059 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 5282 reflections with I > 2σ(I) |
Tmin = 0.710, Tmax = 0.824 | Rint = 0.025 |
21365 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.56 e Å−3 |
6059 reflections | Δρmin = −0.26 e Å−3 |
329 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl11 | 0.06980 (4) | 0.38817 (3) | 0.63046 (4) | 0.03840 (12) | |
Cl12 | 0.03253 (3) | 0.22443 (3) | 0.59138 (4) | 0.03250 (10) | |
Cl13 | 0.08641 (3) | 0.28182 (3) | 0.81751 (3) | 0.02977 (10) | |
O11 | −0.11211 (11) | 0.49245 (7) | 0.67516 (11) | 0.0356 (3) | |
O12 | −0.19628 (11) | 0.49814 (7) | 1.04506 (10) | 0.0344 (3) | |
O13 | −0.19275 (10) | 0.19641 (7) | 0.88626 (11) | 0.0331 (3) | |
O14 | −0.14403 (9) | 0.24163 (7) | 0.72704 (10) | 0.0259 (2) | |
C101 | 0.01528 (13) | 0.30328 (9) | 0.68230 (13) | 0.0244 (3) | |
C102 | −0.10748 (12) | 0.31451 (9) | 0.68615 (14) | 0.0234 (3) | |
H102 | −0.1470 | 0.3261 | 0.6112 | 0.028* | |
C103 | −0.13292 (12) | 0.37435 (9) | 0.76942 (13) | 0.0228 (3) | |
C104 | −0.13137 (13) | 0.45617 (10) | 0.76967 (14) | 0.0268 (3) | |
C105 | −0.10805 (19) | 0.57622 (11) | 0.67624 (18) | 0.0418 (5) | |
H10A | −0.1759 | 0.5966 | 0.6914 | 0.063* | |
H10B | −0.0949 | 0.5948 | 0.6046 | 0.063* | |
H10C | −0.0505 | 0.5934 | 0.7335 | 0.063* | |
C106 | −0.15238 (14) | 0.49424 (10) | 0.86530 (15) | 0.0295 (3) | |
H106 | −0.1486 | 0.5485 | 0.8686 | 0.035* | |
C107 | −0.17912 (13) | 0.45283 (10) | 0.95691 (14) | 0.0267 (3) | |
C108 | −0.21277 (17) | 0.45821 (11) | 1.14487 (16) | 0.0382 (4) | |
H10D | −0.2807 | 0.4307 | 1.1315 | 0.057* | |
H10E | −0.2139 | 0.4955 | 1.2041 | 0.057* | |
H10F | −0.1548 | 0.4216 | 1.1660 | 0.057* | |
C109 | −0.18921 (12) | 0.37180 (9) | 0.95425 (14) | 0.0245 (3) | |
H109 | −0.2112 | 0.3438 | 1.0127 | 0.029* | |
C110 | −0.16447 (12) | 0.33563 (9) | 0.85902 (13) | 0.0225 (3) | |
C111 | −0.16957 (12) | 0.25131 (10) | 0.83304 (14) | 0.0250 (3) | |
Cl21 | 0.35097 (3) | 0.36154 (2) | 0.86744 (4) | 0.02780 (10) | |
Cl22 | 0.33480 (3) | 0.27080 (2) | 0.66440 (3) | 0.02883 (10) | |
Cl32 | 0.38734 (3) | 0.19644 (2) | 0.88102 (3) | 0.02798 (10) | |
O21 | 0.54062 (10) | 0.46814 (6) | 0.85553 (10) | 0.0267 (2) | |
O22 | 0.65546 (10) | 0.51642 (7) | 0.50708 (10) | 0.0290 (3) | |
O23 | 0.61187 (9) | 0.20023 (6) | 0.57770 (10) | 0.0264 (2) | |
O24 | 0.56252 (9) | 0.22630 (6) | 0.74437 (9) | 0.0220 (2) | |
C201 | 0.40543 (12) | 0.28189 (8) | 0.80263 (13) | 0.0204 (3) | |
C202 | 0.52850 (12) | 0.29374 (8) | 0.80197 (13) | 0.0191 (3) | |
H202 | 0.5679 | 0.2962 | 0.8788 | 0.023* | |
C203 | 0.55838 (11) | 0.36196 (8) | 0.73458 (12) | 0.0193 (3) | |
C204 | 0.56441 (12) | 0.44246 (9) | 0.75619 (13) | 0.0214 (3) | |
C205 | 0.54455 (15) | 0.55076 (9) | 0.87515 (15) | 0.0315 (4) | |
H20A | 0.6179 | 0.5688 | 0.8793 | 0.047* | |
H20B | 0.5192 | 0.5619 | 0.9444 | 0.047* | |
H20C | 0.4991 | 0.5769 | 0.8148 | 0.047* | |
C206 | 0.59708 (13) | 0.49068 (9) | 0.67534 (14) | 0.0239 (3) | |
H206 | 0.5995 | 0.5445 | 0.6870 | 0.029* | |
C207 | 0.62647 (12) | 0.46061 (9) | 0.57683 (13) | 0.0228 (3) | |
C208 | 0.69563 (15) | 0.48998 (11) | 0.40926 (15) | 0.0330 (4) | |
H20D | 0.7616 | 0.4612 | 0.4311 | 0.049* | |
H20E | 0.7096 | 0.5342 | 0.3647 | 0.049* | |
H20F | 0.6426 | 0.4568 | 0.3662 | 0.049* | |
C209 | 0.62686 (12) | 0.38057 (9) | 0.55670 (13) | 0.0215 (3) | |
H209 | 0.6489 | 0.3595 | 0.4930 | 0.026* | |
C210 | 0.59189 (11) | 0.33413 (8) | 0.63869 (13) | 0.0193 (3) | |
C211 | 0.59060 (12) | 0.24800 (9) | 0.64337 (13) | 0.0204 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl11 | 0.0378 (2) | 0.0371 (2) | 0.0445 (3) | −0.00823 (18) | 0.01931 (19) | 0.00498 (19) |
Cl12 | 0.0330 (2) | 0.0393 (2) | 0.0265 (2) | 0.00077 (16) | 0.00859 (16) | −0.01034 (16) |
Cl13 | 0.02363 (19) | 0.0419 (2) | 0.0231 (2) | 0.00053 (15) | 0.00183 (14) | −0.00355 (16) |
O11 | 0.0542 (8) | 0.0261 (6) | 0.0284 (7) | 0.0020 (5) | 0.0130 (6) | 0.0065 (5) |
O12 | 0.0499 (8) | 0.0279 (6) | 0.0275 (7) | 0.0059 (5) | 0.0129 (6) | −0.0031 (5) |
O13 | 0.0386 (7) | 0.0263 (6) | 0.0372 (7) | −0.0086 (5) | 0.0147 (5) | 0.0000 (5) |
O14 | 0.0256 (5) | 0.0259 (5) | 0.0271 (6) | −0.0062 (4) | 0.0074 (5) | −0.0041 (4) |
C101 | 0.0250 (7) | 0.0285 (8) | 0.0209 (8) | −0.0038 (6) | 0.0073 (6) | −0.0031 (6) |
C102 | 0.0227 (7) | 0.0254 (7) | 0.0225 (8) | −0.0024 (6) | 0.0044 (6) | −0.0003 (6) |
C103 | 0.0222 (7) | 0.0261 (7) | 0.0202 (8) | 0.0001 (6) | 0.0036 (6) | −0.0002 (6) |
C104 | 0.0295 (8) | 0.0273 (8) | 0.0241 (8) | 0.0025 (6) | 0.0057 (6) | 0.0048 (6) |
C105 | 0.0616 (13) | 0.0259 (9) | 0.0403 (11) | 0.0018 (8) | 0.0154 (9) | 0.0099 (8) |
C106 | 0.0358 (9) | 0.0227 (7) | 0.0304 (9) | 0.0042 (6) | 0.0059 (7) | 0.0016 (6) |
C107 | 0.0269 (8) | 0.0293 (8) | 0.0243 (8) | 0.0053 (6) | 0.0051 (6) | −0.0022 (6) |
C108 | 0.0518 (11) | 0.0368 (10) | 0.0288 (10) | 0.0047 (8) | 0.0151 (8) | −0.0041 (7) |
C109 | 0.0235 (7) | 0.0270 (8) | 0.0238 (8) | 0.0017 (6) | 0.0064 (6) | 0.0015 (6) |
C110 | 0.0183 (7) | 0.0237 (7) | 0.0257 (8) | −0.0003 (5) | 0.0035 (6) | 0.0007 (6) |
C111 | 0.0196 (7) | 0.0282 (8) | 0.0276 (9) | −0.0032 (6) | 0.0050 (6) | −0.0036 (6) |
Cl21 | 0.02578 (19) | 0.02353 (18) | 0.0364 (2) | −0.00070 (14) | 0.01188 (16) | −0.00840 (15) |
Cl22 | 0.02551 (19) | 0.0379 (2) | 0.0222 (2) | −0.00386 (15) | 0.00106 (14) | −0.00351 (15) |
Cl32 | 0.0349 (2) | 0.02229 (18) | 0.0293 (2) | −0.00411 (14) | 0.01264 (16) | 0.00259 (14) |
O21 | 0.0390 (6) | 0.0184 (5) | 0.0254 (6) | −0.0044 (4) | 0.0134 (5) | −0.0061 (4) |
O22 | 0.0376 (6) | 0.0239 (6) | 0.0287 (6) | −0.0019 (5) | 0.0149 (5) | 0.0043 (5) |
O23 | 0.0310 (6) | 0.0227 (5) | 0.0273 (6) | 0.0014 (4) | 0.0101 (5) | −0.0050 (4) |
O24 | 0.0279 (5) | 0.0176 (5) | 0.0221 (6) | 0.0025 (4) | 0.0091 (4) | −0.0006 (4) |
C201 | 0.0241 (7) | 0.0182 (6) | 0.0197 (7) | −0.0011 (5) | 0.0060 (6) | −0.0009 (5) |
C202 | 0.0209 (7) | 0.0179 (6) | 0.0192 (7) | 0.0008 (5) | 0.0054 (5) | −0.0027 (5) |
C203 | 0.0194 (7) | 0.0202 (7) | 0.0187 (7) | −0.0012 (5) | 0.0045 (5) | −0.0006 (5) |
C204 | 0.0224 (7) | 0.0212 (7) | 0.0214 (8) | −0.0008 (5) | 0.0064 (6) | −0.0038 (6) |
C205 | 0.0451 (10) | 0.0192 (7) | 0.0326 (9) | −0.0033 (7) | 0.0131 (7) | −0.0088 (6) |
C206 | 0.0282 (8) | 0.0179 (7) | 0.0271 (8) | −0.0028 (6) | 0.0085 (6) | −0.0018 (6) |
C207 | 0.0223 (7) | 0.0237 (7) | 0.0231 (8) | −0.0025 (6) | 0.0061 (6) | 0.0030 (6) |
C208 | 0.0392 (9) | 0.0335 (9) | 0.0302 (9) | −0.0006 (7) | 0.0177 (7) | 0.0063 (7) |
C209 | 0.0214 (7) | 0.0240 (7) | 0.0199 (8) | −0.0009 (6) | 0.0056 (6) | −0.0023 (6) |
C210 | 0.0175 (6) | 0.0194 (7) | 0.0211 (7) | −0.0011 (5) | 0.0034 (5) | −0.0025 (5) |
C211 | 0.0186 (7) | 0.0219 (7) | 0.0212 (8) | 0.0007 (5) | 0.0049 (5) | −0.0003 (6) |
Cl11—C101 | 1.7599 (17) | Cl21—C201 | 1.7603 (15) |
Cl12—C101 | 1.7738 (16) | Cl22—C201 | 1.7709 (16) |
Cl13—C101 | 1.7697 (17) | Cl32—C201 | 1.7753 (15) |
O11—C104 | 1.354 (2) | O21—C204 | 1.3546 (19) |
O11—C105 | 1.433 (2) | O21—C205 | 1.4321 (18) |
O12—C107 | 1.361 (2) | O22—C207 | 1.3597 (18) |
O12—C108 | 1.429 (2) | O22—C208 | 1.429 (2) |
O13—C111 | 1.199 (2) | O23—C211 | 1.1976 (19) |
O14—C111 | 1.378 (2) | O24—C211 | 1.3733 (19) |
O14—C102 | 1.4411 (19) | O24—C202 | 1.4451 (17) |
C101—C102 | 1.552 (2) | C201—C202 | 1.550 (2) |
C102—C103 | 1.504 (2) | C202—C203 | 1.503 (2) |
C102—H102 | 0.9800 | C202—H202 | 0.9800 |
C103—C110 | 1.379 (2) | C203—C210 | 1.377 (2) |
C103—C104 | 1.399 (2) | C203—C204 | 1.401 (2) |
C104—C106 | 1.387 (2) | C204—C206 | 1.388 (2) |
C105—H10A | 0.9600 | C205—H20A | 0.9600 |
C105—H10B | 0.9600 | C205—H20B | 0.9600 |
C105—H10C | 0.9600 | C205—H20C | 0.9600 |
C106—C107 | 1.398 (2) | C206—C207 | 1.398 (2) |
C106—H106 | 0.9300 | C206—H206 | 0.9300 |
C107—C109 | 1.391 (2) | C207—C209 | 1.390 (2) |
C108—H10D | 0.9600 | C208—H20D | 0.9600 |
C108—H10E | 0.9600 | C208—H20E | 0.9600 |
C108—H10F | 0.9600 | C208—H20F | 0.9600 |
C109—C110 | 1.384 (2) | C209—C210 | 1.393 (2) |
C109—H109 | 0.9300 | C209—H209 | 0.9300 |
C110—C111 | 1.475 (2) | C210—C211 | 1.474 (2) |
C104—O11—C105 | 117.45 (14) | C204—O21—C205 | 117.38 (13) |
C107—O12—C108 | 116.74 (14) | C207—O22—C208 | 116.97 (13) |
C111—O14—C102 | 110.31 (12) | C211—O24—C202 | 110.38 (11) |
C102—C101—Cl11 | 110.35 (11) | C202—C201—Cl21 | 110.72 (10) |
C102—C101—Cl13 | 110.53 (11) | C202—C201—Cl22 | 110.75 (11) |
Cl11—C101—Cl13 | 109.51 (9) | Cl21—C201—Cl22 | 109.46 (8) |
C102—C101—Cl12 | 109.27 (11) | C202—C201—Cl32 | 108.68 (10) |
Cl11—C101—Cl12 | 108.35 (9) | Cl21—C201—Cl32 | 107.98 (8) |
Cl13—C101—Cl12 | 108.78 (9) | Cl22—C201—Cl32 | 109.19 (8) |
O14—C102—C103 | 104.32 (12) | O24—C202—C203 | 103.97 (11) |
O14—C102—C101 | 105.71 (12) | O24—C202—C201 | 105.38 (11) |
C103—C102—C101 | 114.73 (13) | C203—C202—C201 | 115.80 (12) |
O14—C102—H102 | 110.6 | O24—C202—H202 | 110.4 |
C103—C102—H102 | 110.6 | C203—C202—H202 | 110.4 |
C101—C102—H102 | 110.6 | C201—C202—H202 | 110.4 |
C110—C103—C104 | 118.95 (15) | C210—C203—C204 | 118.80 (14) |
C110—C103—C102 | 108.39 (14) | C210—C203—C202 | 108.79 (12) |
C104—C103—C102 | 132.65 (15) | C204—C203—C202 | 132.24 (14) |
O11—C104—C106 | 124.74 (15) | O21—C204—C206 | 124.14 (14) |
O11—C104—C103 | 117.42 (15) | O21—C204—C203 | 118.09 (13) |
C106—C104—C103 | 117.82 (15) | C206—C204—C203 | 117.74 (14) |
O11—C105—H10A | 109.5 | O21—C205—H20A | 109.5 |
O11—C105—H10B | 109.5 | O21—C205—H20B | 109.5 |
H10A—C105—H10B | 109.5 | H20A—C205—H20B | 109.5 |
O11—C105—H10C | 109.5 | O21—C205—H20C | 109.5 |
H10A—C105—H10C | 109.5 | H20A—C205—H20C | 109.5 |
H10B—C105—H10C | 109.5 | H20B—C205—H20C | 109.5 |
C104—C106—C107 | 121.48 (16) | C204—C206—C207 | 121.79 (14) |
C104—C106—H106 | 119.3 | C204—C206—H206 | 119.1 |
C107—C106—H106 | 119.3 | C207—C206—H206 | 119.1 |
O12—C107—C109 | 124.06 (15) | O22—C207—C209 | 125.02 (14) |
O12—C107—C106 | 114.72 (15) | O22—C207—C206 | 113.65 (13) |
C109—C107—C106 | 121.21 (15) | C209—C207—C206 | 121.32 (14) |
O12—C108—H10D | 109.5 | O22—C208—H20D | 109.5 |
O12—C108—H10E | 109.5 | O22—C208—H20E | 109.5 |
H10D—C108—H10E | 109.5 | H20D—C208—H20E | 109.5 |
O12—C108—H10F | 109.5 | O22—C208—H20F | 109.5 |
H10D—C108—H10F | 109.5 | H20D—C208—H20F | 109.5 |
H10E—C108—H10F | 109.5 | H20E—C208—H20F | 109.5 |
C110—C109—C107 | 115.66 (15) | C207—C209—C210 | 115.25 (14) |
C110—C109—H109 | 122.2 | C207—C209—H209 | 122.4 |
C107—C109—H109 | 122.2 | C210—C209—H209 | 122.4 |
C103—C110—C109 | 124.58 (15) | C203—C210—C209 | 124.93 (14) |
C103—C110—C111 | 108.08 (14) | C203—C210—C211 | 107.84 (13) |
C109—C110—C111 | 127.32 (15) | C209—C210—C211 | 127.12 (13) |
O13—C111—O14 | 121.03 (15) | O23—C211—O24 | 121.28 (14) |
O13—C111—C110 | 131.09 (16) | O23—C211—C210 | 130.63 (14) |
O14—C111—C110 | 107.87 (13) | O24—C211—C210 | 108.06 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C109—H109···O23i | 0.93 | 2.57 | 3.328 (2) | 139 |
C202—H202···O23ii | 0.98 | 2.38 | 3.331 (2) | 163 |
C206—H206···Cl32iii | 0.93 | 2.74 | 3.5949 (17) | 154 |
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C11H9Cl3O4 |
Mr | 311.53 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 153 |
a, b, c (Å) | 12.478 (3), 17.100 (4), 12.084 (3) |
β (°) | 99.129 (4) |
V (Å3) | 2545.8 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.51 × 0.40 × 0.28 |
Data collection | |
Diffractometer | Bruker SMART APEX |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.710, 0.824 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21365, 6059, 5282 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.087, 1.04 |
No. of reflections | 6059 |
No. of parameters | 329 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.26 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Bruker, 2002).
D—H···A | D—H | H···A | D···A | D—H···A |
C109—H109···O23i | 0.93 | 2.57 | 3.328 (2) | 138.9 |
C202—H202···O23ii | 0.98 | 2.38 | 3.331 (2) | 163.4 |
C206—H206···Cl32iii | 0.93 | 2.74 | 3.5949 (17) | 153.5 |
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2. |
Isobenzofuran-1-ones (phtalides) are an important class of natural products and are part of the structure of several alkaloids like bicuculline (Ogawa et al., 1996). Furthermore, phtalides are intermediates towards the synthesis of several alkaloids and isocoumarins and exhibit a wide range of biological activities. Thus, 3-n-butylphtalide a constituent of celery seed oil, exhibits anticonvulsant, asthmatic, and antitumor properties (Xiong & Li, 2007); phenolphthalein a well known pH indicator, and its derivatives like 4-Fluoro-3,3-bis-(4-hydroxy-phenyl)-3H-isobenzofuran-1-one are low micromolar inhibitor of the enzyme Thymidylate Synthase, an important target for anticancer chemotherapy (Calo et al., 2004). Diaporthelactone (3-dihydro-4-methoxy-7-methyl-3-oxo-5-isobenzo furan-carboxyaldehyde) and 7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one isolated from the culture of Diaporthe sp., show cytotoxic activity against KB and Raji cell lines (Lin et al., 2005). Three isocoumarins and a benzofuran derivative Pyrenulafuran were isolated from the cultured lichen mycobionts of Pyrenula sp. (Takenaka et al., 2004). Naphthalenone and phthalide metabolites from Lachnum papyraceum possesses weak antimicrobial and phytotoxic activities and weak cytotoxicity (Shan et al., 1997)·The title compound was prepared as an intermediate towards isocoumarins and dihydroisocoumarins.