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The structure of the title compound, C11H9Cl3O4, shows two crystallographically independent but geometrically essentially identical mol­ecules per asymmetric unit. The meth­oxy groups lie in the plane of the aromatic system, the relevant C—O—C—C and C—O—C—C torsion angles being −173.7 (2) and 3.1 (3)°, and 174.7 (1) and 3.2 (3)° for the two mol­ecules. Mol­ecules are packed in sheets parallel to the (100) plane, with various inter­molecular C—H...O and C—H...Cl contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049409/dn2237sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049409/dn2237Isup2.hkl
Contains datablock I

CCDC reference: 667367

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Refinement top

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.

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
(±)-4,6-Dimethoxy-3-(trichloromethyl)isobenzofuran-1(3H)-one top
Crystal data top
C11H9Cl3O4F(000) = 1264
Mr = 311.53Dx = 1.626 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 962 reflections
a = 12.478 (3) Åθ = 2.6–28.3°
b = 17.100 (4) ŵ = 0.72 mm1
c = 12.084 (3) ÅT = 153 K
β = 99.129 (4)°Prism, colourless
V = 2545.8 (11) Å30.51 × 0.40 × 0.28 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer
6059 independent reflections
Radiation source: sealed tube5282 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 27.9°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1616
Tmin = 0.710, Tmax = 0.824k = 2222
21365 measured reflectionsl = 1515
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-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 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C11H9Cl3O4V = 2545.8 (11) Å3
Mr = 311.53Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.478 (3) ŵ = 0.72 mm1
b = 17.100 (4) ÅT = 153 K
c = 12.084 (3) Å0.51 × 0.40 × 0.28 mm
β = 99.129 (4)°
Data collection top
Bruker SMART APEX
diffractometer
6059 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
5282 reflections with I > 2σ(I)
Tmin = 0.710, Tmax = 0.824Rint = 0.025
21365 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.04Δρmax = 0.56 e Å3
6059 reflectionsΔρmin = 0.26 e Å3
329 parameters
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
Cl110.06980 (4)0.38817 (3)0.63046 (4)0.03840 (12)
Cl120.03253 (3)0.22443 (3)0.59138 (4)0.03250 (10)
Cl130.08641 (3)0.28182 (3)0.81751 (3)0.02977 (10)
O110.11211 (11)0.49245 (7)0.67516 (11)0.0356 (3)
O120.19628 (11)0.49814 (7)1.04506 (10)0.0344 (3)
O130.19275 (10)0.19641 (7)0.88626 (11)0.0331 (3)
O140.14403 (9)0.24163 (7)0.72704 (10)0.0259 (2)
C1010.01528 (13)0.30328 (9)0.68230 (13)0.0244 (3)
C1020.10748 (12)0.31451 (9)0.68615 (14)0.0234 (3)
H1020.14700.32610.61120.028*
C1030.13292 (12)0.37435 (9)0.76942 (13)0.0228 (3)
C1040.13137 (13)0.45617 (10)0.76967 (14)0.0268 (3)
C1050.10805 (19)0.57622 (11)0.67624 (18)0.0418 (5)
H10A0.17590.59660.69140.063*
H10B0.09490.59480.60460.063*
H10C0.05050.59340.73350.063*
C1060.15238 (14)0.49424 (10)0.86530 (15)0.0295 (3)
H1060.14860.54850.86860.035*
C1070.17912 (13)0.45283 (10)0.95691 (14)0.0267 (3)
C1080.21277 (17)0.45821 (11)1.14487 (16)0.0382 (4)
H10D0.28070.43071.13150.057*
H10E0.21390.49551.20410.057*
H10F0.15480.42161.16600.057*
C1090.18921 (12)0.37180 (9)0.95425 (14)0.0245 (3)
H1090.21120.34381.01270.029*
C1100.16447 (12)0.33563 (9)0.85902 (13)0.0225 (3)
C1110.16957 (12)0.25131 (10)0.83304 (14)0.0250 (3)
Cl210.35097 (3)0.36154 (2)0.86744 (4)0.02780 (10)
Cl220.33480 (3)0.27080 (2)0.66440 (3)0.02883 (10)
Cl320.38734 (3)0.19644 (2)0.88102 (3)0.02798 (10)
O210.54062 (10)0.46814 (6)0.85553 (10)0.0267 (2)
O220.65546 (10)0.51642 (7)0.50708 (10)0.0290 (3)
O230.61187 (9)0.20023 (6)0.57770 (10)0.0264 (2)
O240.56252 (9)0.22630 (6)0.74437 (9)0.0220 (2)
C2010.40543 (12)0.28189 (8)0.80263 (13)0.0204 (3)
C2020.52850 (12)0.29374 (8)0.80197 (13)0.0191 (3)
H2020.56790.29620.87880.023*
C2030.55838 (11)0.36196 (8)0.73458 (12)0.0193 (3)
C2040.56441 (12)0.44246 (9)0.75619 (13)0.0214 (3)
C2050.54455 (15)0.55076 (9)0.87515 (15)0.0315 (4)
H20A0.61790.56880.87930.047*
H20B0.51920.56190.94440.047*
H20C0.49910.57690.81480.047*
C2060.59708 (13)0.49068 (9)0.67534 (14)0.0239 (3)
H2060.59950.54450.68700.029*
C2070.62647 (12)0.46061 (9)0.57683 (13)0.0228 (3)
C2080.69563 (15)0.48998 (11)0.40926 (15)0.0330 (4)
H20D0.76160.46120.43110.049*
H20E0.70960.53420.36470.049*
H20F0.64260.45680.36620.049*
C2090.62686 (12)0.38057 (9)0.55670 (13)0.0215 (3)
H2090.64890.35950.49300.026*
C2100.59189 (11)0.33413 (8)0.63869 (13)0.0193 (3)
C2110.59060 (12)0.24800 (9)0.64337 (13)0.0204 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl110.0378 (2)0.0371 (2)0.0445 (3)0.00823 (18)0.01931 (19)0.00498 (19)
Cl120.0330 (2)0.0393 (2)0.0265 (2)0.00077 (16)0.00859 (16)0.01034 (16)
Cl130.02363 (19)0.0419 (2)0.0231 (2)0.00053 (15)0.00183 (14)0.00355 (16)
O110.0542 (8)0.0261 (6)0.0284 (7)0.0020 (5)0.0130 (6)0.0065 (5)
O120.0499 (8)0.0279 (6)0.0275 (7)0.0059 (5)0.0129 (6)0.0031 (5)
O130.0386 (7)0.0263 (6)0.0372 (7)0.0086 (5)0.0147 (5)0.0000 (5)
O140.0256 (5)0.0259 (5)0.0271 (6)0.0062 (4)0.0074 (5)0.0041 (4)
C1010.0250 (7)0.0285 (8)0.0209 (8)0.0038 (6)0.0073 (6)0.0031 (6)
C1020.0227 (7)0.0254 (7)0.0225 (8)0.0024 (6)0.0044 (6)0.0003 (6)
C1030.0222 (7)0.0261 (7)0.0202 (8)0.0001 (6)0.0036 (6)0.0002 (6)
C1040.0295 (8)0.0273 (8)0.0241 (8)0.0025 (6)0.0057 (6)0.0048 (6)
C1050.0616 (13)0.0259 (9)0.0403 (11)0.0018 (8)0.0154 (9)0.0099 (8)
C1060.0358 (9)0.0227 (7)0.0304 (9)0.0042 (6)0.0059 (7)0.0016 (6)
C1070.0269 (8)0.0293 (8)0.0243 (8)0.0053 (6)0.0051 (6)0.0022 (6)
C1080.0518 (11)0.0368 (10)0.0288 (10)0.0047 (8)0.0151 (8)0.0041 (7)
C1090.0235 (7)0.0270 (8)0.0238 (8)0.0017 (6)0.0064 (6)0.0015 (6)
C1100.0183 (7)0.0237 (7)0.0257 (8)0.0003 (5)0.0035 (6)0.0007 (6)
C1110.0196 (7)0.0282 (8)0.0276 (9)0.0032 (6)0.0050 (6)0.0036 (6)
Cl210.02578 (19)0.02353 (18)0.0364 (2)0.00070 (14)0.01188 (16)0.00840 (15)
Cl220.02551 (19)0.0379 (2)0.0222 (2)0.00386 (15)0.00106 (14)0.00351 (15)
Cl320.0349 (2)0.02229 (18)0.0293 (2)0.00411 (14)0.01264 (16)0.00259 (14)
O210.0390 (6)0.0184 (5)0.0254 (6)0.0044 (4)0.0134 (5)0.0061 (4)
O220.0376 (6)0.0239 (6)0.0287 (6)0.0019 (5)0.0149 (5)0.0043 (5)
O230.0310 (6)0.0227 (5)0.0273 (6)0.0014 (4)0.0101 (5)0.0050 (4)
O240.0279 (5)0.0176 (5)0.0221 (6)0.0025 (4)0.0091 (4)0.0006 (4)
C2010.0241 (7)0.0182 (6)0.0197 (7)0.0011 (5)0.0060 (6)0.0009 (5)
C2020.0209 (7)0.0179 (6)0.0192 (7)0.0008 (5)0.0054 (5)0.0027 (5)
C2030.0194 (7)0.0202 (7)0.0187 (7)0.0012 (5)0.0045 (5)0.0006 (5)
C2040.0224 (7)0.0212 (7)0.0214 (8)0.0008 (5)0.0064 (6)0.0038 (6)
C2050.0451 (10)0.0192 (7)0.0326 (9)0.0033 (7)0.0131 (7)0.0088 (6)
C2060.0282 (8)0.0179 (7)0.0271 (8)0.0028 (6)0.0085 (6)0.0018 (6)
C2070.0223 (7)0.0237 (7)0.0231 (8)0.0025 (6)0.0061 (6)0.0030 (6)
C2080.0392 (9)0.0335 (9)0.0302 (9)0.0006 (7)0.0177 (7)0.0063 (7)
C2090.0214 (7)0.0240 (7)0.0199 (8)0.0009 (6)0.0056 (6)0.0023 (6)
C2100.0175 (6)0.0194 (7)0.0211 (7)0.0011 (5)0.0034 (5)0.0025 (5)
C2110.0186 (7)0.0219 (7)0.0212 (8)0.0007 (5)0.0049 (5)0.0003 (6)
Geometric parameters (Å, º) top
Cl11—C1011.7599 (17)Cl21—C2011.7603 (15)
Cl12—C1011.7738 (16)Cl22—C2011.7709 (16)
Cl13—C1011.7697 (17)Cl32—C2011.7753 (15)
O11—C1041.354 (2)O21—C2041.3546 (19)
O11—C1051.433 (2)O21—C2051.4321 (18)
O12—C1071.361 (2)O22—C2071.3597 (18)
O12—C1081.429 (2)O22—C2081.429 (2)
O13—C1111.199 (2)O23—C2111.1976 (19)
O14—C1111.378 (2)O24—C2111.3733 (19)
O14—C1021.4411 (19)O24—C2021.4451 (17)
C101—C1021.552 (2)C201—C2021.550 (2)
C102—C1031.504 (2)C202—C2031.503 (2)
C102—H1020.9800C202—H2020.9800
C103—C1101.379 (2)C203—C2101.377 (2)
C103—C1041.399 (2)C203—C2041.401 (2)
C104—C1061.387 (2)C204—C2061.388 (2)
C105—H10A0.9600C205—H20A0.9600
C105—H10B0.9600C205—H20B0.9600
C105—H10C0.9600C205—H20C0.9600
C106—C1071.398 (2)C206—C2071.398 (2)
C106—H1060.9300C206—H2060.9300
C107—C1091.391 (2)C207—C2091.390 (2)
C108—H10D0.9600C208—H20D0.9600
C108—H10E0.9600C208—H20E0.9600
C108—H10F0.9600C208—H20F0.9600
C109—C1101.384 (2)C209—C2101.393 (2)
C109—H1090.9300C209—H2090.9300
C110—C1111.475 (2)C210—C2111.474 (2)
C104—O11—C105117.45 (14)C204—O21—C205117.38 (13)
C107—O12—C108116.74 (14)C207—O22—C208116.97 (13)
C111—O14—C102110.31 (12)C211—O24—C202110.38 (11)
C102—C101—Cl11110.35 (11)C202—C201—Cl21110.72 (10)
C102—C101—Cl13110.53 (11)C202—C201—Cl22110.75 (11)
Cl11—C101—Cl13109.51 (9)Cl21—C201—Cl22109.46 (8)
C102—C101—Cl12109.27 (11)C202—C201—Cl32108.68 (10)
Cl11—C101—Cl12108.35 (9)Cl21—C201—Cl32107.98 (8)
Cl13—C101—Cl12108.78 (9)Cl22—C201—Cl32109.19 (8)
O14—C102—C103104.32 (12)O24—C202—C203103.97 (11)
O14—C102—C101105.71 (12)O24—C202—C201105.38 (11)
C103—C102—C101114.73 (13)C203—C202—C201115.80 (12)
O14—C102—H102110.6O24—C202—H202110.4
C103—C102—H102110.6C203—C202—H202110.4
C101—C102—H102110.6C201—C202—H202110.4
C110—C103—C104118.95 (15)C210—C203—C204118.80 (14)
C110—C103—C102108.39 (14)C210—C203—C202108.79 (12)
C104—C103—C102132.65 (15)C204—C203—C202132.24 (14)
O11—C104—C106124.74 (15)O21—C204—C206124.14 (14)
O11—C104—C103117.42 (15)O21—C204—C203118.09 (13)
C106—C104—C103117.82 (15)C206—C204—C203117.74 (14)
O11—C105—H10A109.5O21—C205—H20A109.5
O11—C105—H10B109.5O21—C205—H20B109.5
H10A—C105—H10B109.5H20A—C205—H20B109.5
O11—C105—H10C109.5O21—C205—H20C109.5
H10A—C105—H10C109.5H20A—C205—H20C109.5
H10B—C105—H10C109.5H20B—C205—H20C109.5
C104—C106—C107121.48 (16)C204—C206—C207121.79 (14)
C104—C106—H106119.3C204—C206—H206119.1
C107—C106—H106119.3C207—C206—H206119.1
O12—C107—C109124.06 (15)O22—C207—C209125.02 (14)
O12—C107—C106114.72 (15)O22—C207—C206113.65 (13)
C109—C107—C106121.21 (15)C209—C207—C206121.32 (14)
O12—C108—H10D109.5O22—C208—H20D109.5
O12—C108—H10E109.5O22—C208—H20E109.5
H10D—C108—H10E109.5H20D—C208—H20E109.5
O12—C108—H10F109.5O22—C208—H20F109.5
H10D—C108—H10F109.5H20D—C208—H20F109.5
H10E—C108—H10F109.5H20E—C208—H20F109.5
C110—C109—C107115.66 (15)C207—C209—C210115.25 (14)
C110—C109—H109122.2C207—C209—H209122.4
C107—C109—H109122.2C210—C209—H209122.4
C103—C110—C109124.58 (15)C203—C210—C209124.93 (14)
C103—C110—C111108.08 (14)C203—C210—C211107.84 (13)
C109—C110—C111127.32 (15)C209—C210—C211127.12 (13)
O13—C111—O14121.03 (15)O23—C211—O24121.28 (14)
O13—C111—C110131.09 (16)O23—C211—C210130.63 (14)
O14—C111—C110107.87 (13)O24—C211—C210108.06 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C109—H109···O23i0.932.573.328 (2)139
C202—H202···O23ii0.982.383.331 (2)163
C206—H206···Cl32iii0.932.743.5949 (17)154
Symmetry codes: (i) x1, 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 formulaC11H9Cl3O4
Mr311.53
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)12.478 (3), 17.100 (4), 12.084 (3)
β (°) 99.129 (4)
V3)2545.8 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.72
Crystal size (mm)0.51 × 0.40 × 0.28
Data collection
DiffractometerBruker SMART APEX
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.710, 0.824
No. of measured, independent and
observed [I > 2σ(I)] reflections
21365, 6059, 5282
Rint0.025
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.087, 1.04
No. of reflections6059
No. of parameters329
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.26

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Bruker, 2002).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C109—H109···O23i0.932.573.328 (2)138.9
C202—H202···O23ii0.982.383.331 (2)163.4
C206—H206···Cl32iii0.932.743.5949 (17)153.5
Symmetry codes: (i) x1, y+1/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x+1, y+1/2, z+3/2.
 

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