| Methyl 4',5-dichloro-2-hy-droxy-4,6-dimethyl-biphenyl-3-carboxyl-ate. | |
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PMID: 22606160 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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In the title compound, C(16)H(14)Cl(2)O(3), the dihedral angle between the mean planes of the two benzene rings is 55.30 (5)°. The methyl ester group lies within the ring plane due to an intra-molecular O-H⋯O hydrogen bond [maximum deviation from the C(8)O(2) mean plane is 0.0383 (13) Å]. In the crystal, mol-ecules are held together by rather weak C-H⋯O hydrogen bonds. |
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Authors:
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Muhammad Adeel; Peter Langer; Martin Hein; Helmut Reinke |
Publication Detail:
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Type: Journal Article Date: 2012-03-28 |
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Title: Acta crystallographica. Section E, Structure reports online Volume: 68 ISSN: 1600-5368 ISO Abbreviation: Acta Crystallogr Sect E Struct Rep Online Publication Date: 2012 Apr |
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Created Date: 2012-05-18 Completed Date: 2012-10-02 Revised Date: 2013-03-01 |
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Nlm Unique ID: 101089178 Medline TA: Acta Crystallogr Sect E Struct Rep Online Country: United States |
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Languages: eng Pagination: o1224 Citation Subset: - |
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Journal Information Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online Journal ID (iso-abbrev): Acta Crystallogr Sect E Struct Rep Online Journal ID (publisher-id): Acta Cryst. E ISSN: 1600-5368 Publisher: International Union of Crystallography |
Article Information Download PDF  A full version of this article is available from Crystallography Journals Online.© Adeel et al. 2012 open-access: Received Day: 23 Month: 2 Year: 2012 Accepted Day: 23 Month: 3 Year: 2012 collection publication date: Day: 01 Month: 4 Year: 2012 Electronic publication date: Day: 28 Month: 3 Year: 2012 pmc-release publication date: Day: 28 Month: 3 Year: 2012 Volume: 68 Issue: Pt 4 First Page: o1224 Last Page: o1224 ID: 3344157 PubMed Id: 22606160 Publisher Id: pv2517 DOI: 10.1107/S1600536812012676 Coden: ACSEBH Publisher Item Identifier: S1600536812012676 |
| Methyl 4′,5-dichloro-2-hydroxy-4,6-dimethylbiphenyl-3-carboxylate Alternate Title:C16H14Cl2O3 | |
| Muhammad Adeela* | |
| Peter Langerb | |
| Martin Heinb | |
| Helmut Reinkec | |
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aGomal University, Department of Chemistry, Dera Ismail Khan (KPK), Pakistan |
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bUniversität Rostock, Institut für Chemie, Abteilung für Organische Chemie, Albert-Einstein-Strasse 3a, 18059 Rostock, Germany |
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cUniversität Rostock, Institut für Chemie, Abteilung für Anorganische Chemie, Albert-Einstein-Strasse 3a, 18059 Rostock, Germany |
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| Correspondence: Correspondence e-mail: muhammad_adeel2000@yahoo.com |
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For pharmacological relevance of salicylates and the synthesis of the title compound, see: Adeel, Rashid et al. (2009 ▶). For related structures, see: Adeel, Ali et al. (2009 ▶); Adeel, Langer et al. (2011 ▶).[Chemical Structure ID: scheme1]
- C16H14Cl2O3
- Mr = 325.19
- Monoclinic,
- a = 4.0956 (5) Å
- b = 13.3066 (17) Å
- c = 13.3656 (16) Å
- β = 92.711 (7)°
- V = 727.59 (16) Å3
- Z = 2
- Mo Kα radiation
- μ = 0.45 mm−1
- T = 173 K
- 0.65 × 0.50 × 0.06 mm
- Bruker APEXII CCD area-detector diffractometer
- Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) Tmin = 0.758, Tmax = 0.973
- 9311 measured reflections
- 3754 independent reflections
- 3331 reflections with I > 2σ(I)
- Rint = 0.022
- R[F2 > 2σ(F2)] = 0.030
- wR(F2) = 0.074
- S = 1.04
- 3754 reflections
- 197 parameters
- 1 restraint
- H atoms treated by a mixture of independent and constrained refinement
- Δρmax = 0.32 e Å−3
- Δρmin = −0.18 e Å−3
- Absolute structure: Flack (1983 ▶), 1569 Friedel pairs
- Flack parameter: 0.05 (5)
Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012676/pv2517sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012676/pv2517Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812012676/pv2517Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Notes
fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2517).
Financial support from the Higher Education Commission of Pakistan (HEC) under the resource grant programe and the World University Service, Deutsches Kommitee, is gratefully acknowledged.
Functionalized biaryls containing a 3-arylsalicylate substructure occur in a variety of pharmacologically relevant natural products (Adeel, Rashid & et al., 2009). A sterically encumbered and functionalized biaryl, the title compound, was synthesized from 4-(4-methoxyphenyl)-1,3-bis(trimethylsilyloxy)-1,3-butadiene. In this paper, the crystal structure of the title compound has been presented.
In the title compound (Fig. 1), the dihedral angle between the mean planes of the two benzene rings is 55.30 (5)°. The methyl ester group lies within the ring plane due to an intramolecular O—H···O hydrogen bond; the maximum deviation of any atom from the mean-plane of atoms C1–C8/O1/O2 is 0.0383 (13) Å for C2. In the crystal, molecules are held together by rather weak intermolecular C—H···O hydrogen bonds along the a-axis (Fig. 2 & Table 1).
The title compound was prepared according to a previously published procedure (Adeel, Rashid et al., 2009) using 3-(Silyloxy)-2-en-1-ones (332 mg, 1.65 mmol), 1,3-bis(silyl enol ethers) (612 mg, 1.65 mmol) and TiCl4 (0.18 ml, 1.65 mmol) in CH2Cl2 (4 mL). The title compound was isolated as a colorless prisms; (190 mg, 40%, m.p. = 367–369 K). Crystallization from a saturated dichloromethane/methanol (9:1) solution at ambient temperature gave colourless crystals suitable for X-ray crystallographic studies.
An absolute structure was determined by using 1569 Friedel pairs. The H atom bonded to O1 was located from a difference Fourier map and refined freely. Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.98 (methyl) or 0.95 Å (aryl) with Uiso(H) = 1.5 times Ueq(C) (methyl H) or 1.2 times Ueq(C) (aryl H); torsion angles of all methyl groups were allowed to refine.
Symmetry code: (i) x−1, y, z.
References
| Adeel, M., Ali, I., Langer, P. & Villinger, A. (2009). Acta Cryst. E65, o2176. | |
| Adeel, M., Langer, P. & Villinger, A. (2011). Acta Cryst. E67, o2336. | |
| Adeel, M., Rashid, M. A., Rasool, N., Ahmad, R., Villinger, A., Reinke, H., Fischer, C. & Langer, P. (2009). Synthesis, pp. 243–250. | |
| Bruker (2003). APEX2 and SAINT Bruker–Nonius Inc., Madison, Wisconsin, USA. | |
| Bruker (2005). SADABS Bruker–Nonius Inc., Madison, Wisconsin, USA. | |
| Flack, H. D. (1983). Acta Cryst. A39, 876–881. | |
| Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. |
Figures
[Figure ID: Fap1] |
Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. |
[Figure ID: Fap2] |
Fig. 2.
A view of the intermolecular (C—-H···O) and intramolecular (O—H···O and C—H···Cl) hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen- bonding were omitted for clarity. |
Tables
| C16H14Cl2O3 | F(000) = 336 |
| Mr = 325.19 | Dx = 1.484 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2yb | Cell parameters from 4567 reflections |
| a = 4.0956 (5) Å | θ = 2.2–29.8° |
| b = 13.3066 (17) Å | µ = 0.45 mm−1 |
| c = 13.3656 (16) Å | T = 173 K |
| β = 92.711 (7)° | Plate, colourless |
| V = 727.59 (16) Å3 | 0.65 × 0.50 × 0.06 mm |
| Z = 2 |
| Bruker APEXII CCD area-detector diffractometer | 3754 independent reflections |
| Radiation source: fine-focus sealed tube | 3331 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.022 |
| φ and ω scans | θmax = 29.9°, θmin = 3.1° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −5→5 |
| Tmin = 0.758, Tmax = 0.973 | k = −18→15 |
| 9311 measured reflections | l = −17→18 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0402P)2 + 0.0613P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 3754 reflections | Δρmax = 0.32 e Å−3 |
| 197 parameters | Δρmin = −0.18 e Å−3 |
| 1 restraint | Absolute structure: Flack (1983), 1569 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.05 (5) |
| 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 | ||
| Cl1 | −0.12949 (11) | 0.03726 (3) | 0.31348 (3) | 0.02951 (11) | |
| Cl2 | −0.24707 (13) | 0.25736 (5) | −0.35858 (3) | 0.04068 (13) | |
| O1 | 0.4723 (4) | 0.47523 (11) | 0.24494 (11) | 0.0385 (3) | |
| O2 | 0.4797 (4) | 0.39445 (11) | 0.39014 (10) | 0.0397 (4) | |
| O3 | 0.1939 (3) | 0.40131 (10) | 0.08937 (10) | 0.0257 (3) | |
| H3O | 0.278 (6) | 0.437 (2) | 0.1272 (19) | 0.046 (8)* | |
| C1 | 0.2187 (4) | 0.31271 (13) | 0.24869 (12) | 0.0179 (3) | |
| C2 | 0.1324 (4) | 0.31873 (13) | 0.14433 (12) | 0.0187 (3) | |
| C3 | −0.0198 (3) | 0.23718 (12) | 0.09202 (11) | 0.0167 (3) | |
| C4 | −0.1037 (4) | 0.15145 (12) | 0.14643 (12) | 0.0168 (3) | |
| C5 | −0.0227 (4) | 0.14812 (13) | 0.25056 (12) | 0.0182 (3) | |
| C6 | 0.1376 (4) | 0.22493 (13) | 0.30390 (12) | 0.0190 (3) | |
| C7 | 0.3994 (4) | 0.40092 (14) | 0.29314 (13) | 0.0219 (3) | |
| C8 | 0.6450 (6) | 0.48150 (18) | 0.43503 (17) | 0.0449 (5) | |
| H8A | 0.8541 | 0.4918 | 0.4037 | 0.067* | |
| H8B | 0.6846 | 0.4701 | 0.5070 | 0.067* | |
| H8C | 0.5076 | 0.5412 | 0.4245 | 0.067* | |
| C9 | −0.2826 (4) | 0.06380 (13) | 0.09765 (13) | 0.0218 (3) | |
| H9A | −0.3475 | 0.0810 | 0.0282 | 0.033* | |
| H9B | −0.4779 | 0.0486 | 0.1345 | 0.033* | |
| H9C | −0.1388 | 0.0049 | 0.0985 | 0.033* | |
| C10 | 0.2165 (5) | 0.21357 (15) | 0.41504 (13) | 0.0309 (4) | |
| H10A | 0.1166 | 0.1517 | 0.4391 | 0.046* | |
| H10B | 0.1299 | 0.2714 | 0.4507 | 0.046* | |
| H10C | 0.4540 | 0.2102 | 0.4273 | 0.046* | |
| C11 | −0.0770 (4) | 0.24329 (12) | −0.01993 (11) | 0.0173 (3) | |
| C12 | −0.2543 (4) | 0.32261 (13) | −0.06551 (12) | 0.0192 (3) | |
| H12 | −0.3402 | 0.3741 | −0.0251 | 0.023* | |
| C13 | −0.3060 (4) | 0.32687 (14) | −0.16939 (12) | 0.0221 (3) | |
| H13 | −0.4280 | 0.3805 | −0.1995 | 0.026* | |
| C14 | −0.1769 (4) | 0.25169 (15) | −0.22847 (12) | 0.0225 (3) | |
| C15 | 0.0039 (4) | 0.17324 (14) | −0.18631 (13) | 0.0235 (3) | |
| H15 | 0.0942 | 0.1231 | −0.2274 | 0.028* | |
| C16 | 0.0510 (4) | 0.16929 (13) | −0.08213 (13) | 0.0221 (3) | |
| H16 | 0.1725 | 0.1152 | −0.0526 | 0.026* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0416 (2) | 0.02195 (19) | 0.0246 (2) | −0.00629 (19) | −0.00240 (16) | 0.00732 (18) |
| Cl2 | 0.0571 (3) | 0.0497 (3) | 0.01488 (19) | −0.0008 (3) | −0.00219 (17) | −0.0013 (2) |
| O1 | 0.0570 (9) | 0.0258 (7) | 0.0317 (7) | −0.0156 (6) | −0.0074 (6) | −0.0003 (6) |
| O2 | 0.0599 (9) | 0.0338 (8) | 0.0244 (7) | −0.0174 (7) | −0.0105 (6) | −0.0054 (6) |
| O3 | 0.0398 (7) | 0.0188 (6) | 0.0184 (6) | −0.0080 (5) | −0.0001 (5) | 0.0008 (5) |
| C1 | 0.0206 (7) | 0.0157 (8) | 0.0173 (7) | 0.0005 (6) | −0.0005 (6) | −0.0032 (6) |
| C2 | 0.0214 (7) | 0.0175 (8) | 0.0174 (7) | 0.0018 (6) | 0.0028 (6) | 0.0005 (6) |
| C3 | 0.0175 (7) | 0.0176 (8) | 0.0148 (7) | 0.0043 (6) | −0.0007 (5) | −0.0005 (6) |
| C4 | 0.0163 (6) | 0.0159 (7) | 0.0180 (7) | 0.0027 (6) | −0.0002 (5) | −0.0014 (6) |
| C5 | 0.0217 (7) | 0.0160 (7) | 0.0168 (7) | 0.0020 (6) | −0.0007 (6) | 0.0038 (6) |
| C6 | 0.0192 (6) | 0.0222 (8) | 0.0152 (7) | 0.0035 (6) | −0.0017 (5) | −0.0009 (6) |
| C7 | 0.0231 (8) | 0.0214 (8) | 0.0212 (8) | 0.0000 (6) | −0.0005 (6) | −0.0049 (6) |
| C8 | 0.0619 (14) | 0.0381 (13) | 0.0331 (11) | −0.0169 (10) | −0.0135 (10) | −0.0141 (10) |
| C9 | 0.0226 (7) | 0.0184 (8) | 0.0239 (8) | −0.0016 (6) | −0.0039 (6) | 0.0010 (6) |
| C10 | 0.0473 (10) | 0.0283 (10) | 0.0163 (8) | −0.0045 (8) | −0.0079 (7) | 0.0034 (7) |
| C11 | 0.0189 (7) | 0.0181 (8) | 0.0148 (7) | −0.0018 (6) | −0.0013 (5) | −0.0002 (6) |
| C12 | 0.0221 (7) | 0.0186 (8) | 0.0167 (7) | 0.0010 (6) | 0.0012 (6) | −0.0007 (6) |
| C13 | 0.0274 (8) | 0.0201 (8) | 0.0184 (8) | 0.0007 (6) | −0.0023 (6) | 0.0025 (6) |
| C14 | 0.0237 (7) | 0.0297 (9) | 0.0139 (7) | −0.0046 (7) | −0.0002 (5) | −0.0003 (7) |
| C15 | 0.0238 (7) | 0.0256 (9) | 0.0211 (8) | 0.0011 (7) | 0.0010 (6) | −0.0083 (7) |
| C16 | 0.0205 (7) | 0.0222 (9) | 0.0231 (8) | 0.0030 (6) | −0.0028 (6) | −0.0036 (7) |
| Cl1—C5 | 1.7633 (17) | C8—H8B | 0.9800 |
| Cl2—C14 | 1.7507 (16) | C8—H8C | 0.9800 |
| O1—C7 | 1.225 (2) | C9—H9A | 0.9800 |
| O2—C7 | 1.325 (2) | C9—H9B | 0.9800 |
| O2—C8 | 1.457 (2) | C9—H9C | 0.9800 |
| O3—C2 | 1.352 (2) | C10—H10A | 0.9800 |
| O3—H3O | 0.77 (3) | C10—H10B | 0.9800 |
| C1—C2 | 1.425 (2) | C10—H10C | 0.9800 |
| C1—C6 | 1.429 (2) | C11—C12 | 1.404 (2) |
| C1—C7 | 1.496 (2) | C11—C16 | 1.406 (2) |
| C2—C3 | 1.419 (2) | C12—C13 | 1.396 (2) |
| C3—C4 | 1.404 (2) | C12—H12 | 0.9500 |
| C3—C11 | 1.506 (2) | C13—C14 | 1.394 (2) |
| C4—C5 | 1.416 (2) | C13—H13 | 0.9500 |
| C4—C9 | 1.509 (2) | C14—C15 | 1.384 (3) |
| C5—C6 | 1.393 (2) | C15—C16 | 1.398 (2) |
| C6—C10 | 1.513 (2) | C15—H15 | 0.9500 |
| C8—H8A | 0.9800 | C16—H16 | 0.9500 |
| C7—O2—C8 | 116.13 (16) | C4—C9—H9B | 109.5 |
| C2—O3—H3O | 104 (2) | H9A—C9—H9B | 109.5 |
| C2—C1—C6 | 119.90 (14) | C4—C9—H9C | 109.5 |
| C2—C1—C7 | 116.10 (15) | H9A—C9—H9C | 109.5 |
| C6—C1—C7 | 123.99 (14) | H9B—C9—H9C | 109.5 |
| O3—C2—C3 | 116.27 (14) | C6—C10—H10A | 109.5 |
| O3—C2—C1 | 122.25 (15) | C6—C10—H10B | 109.5 |
| C3—C2—C1 | 121.47 (15) | H10A—C10—H10B | 109.5 |
| C4—C3—C2 | 118.60 (14) | C6—C10—H10C | 109.5 |
| C4—C3—C11 | 121.88 (14) | H10A—C10—H10C | 109.5 |
| C2—C3—C11 | 119.49 (14) | H10B—C10—H10C | 109.5 |
| C3—C4—C5 | 118.87 (14) | C12—C11—C16 | 118.01 (14) |
| C3—C4—C9 | 121.99 (14) | C12—C11—C3 | 121.66 (14) |
| C5—C4—C9 | 119.13 (15) | C16—C11—C3 | 120.33 (14) |
| C6—C5—C4 | 124.26 (15) | C13—C12—C11 | 120.89 (15) |
| C6—C5—Cl1 | 119.44 (12) | C13—C12—H12 | 119.6 |
| C4—C5—Cl1 | 116.29 (13) | C11—C12—H12 | 119.6 |
| C5—C6—C1 | 116.81 (14) | C14—C13—C12 | 119.38 (15) |
| C5—C6—C10 | 120.19 (15) | C14—C13—H13 | 120.3 |
| C1—C6—C10 | 123.00 (14) | C12—C13—H13 | 120.3 |
| O1—C7—O2 | 120.77 (16) | C15—C14—C13 | 121.36 (15) |
| O1—C7—C1 | 123.58 (16) | C15—C14—Cl2 | 119.75 (13) |
| O2—C7—C1 | 115.66 (15) | C13—C14—Cl2 | 118.88 (14) |
| O2—C8—H8A | 109.5 | C14—C15—C16 | 118.68 (15) |
| O2—C8—H8B | 109.5 | C14—C15—H15 | 120.7 |
| H8A—C8—H8B | 109.5 | C16—C15—H15 | 120.7 |
| O2—C8—H8C | 109.5 | C15—C16—C11 | 121.67 (15) |
| H8A—C8—H8C | 109.5 | C15—C16—H16 | 119.2 |
| H8B—C8—H8C | 109.5 | C11—C16—H16 | 119.2 |
| C4—C9—H9A | 109.5 | ||
| C6—C1—C2—O3 | 177.81 (15) | C2—C1—C6—C10 | −179.09 (15) |
| C7—C1—C2—O3 | −3.4 (2) | C7—C1—C6—C10 | 2.3 (2) |
| C6—C1—C2—C3 | −3.0 (2) | C8—O2—C7—O1 | 2.3 (3) |
| C7—C1—C2—C3 | 175.71 (14) | C8—O2—C7—C1 | −177.79 (17) |
| O3—C2—C3—C4 | −176.93 (14) | C2—C1—C7—O1 | 0.1 (2) |
| C1—C2—C3—C4 | 3.9 (2) | C6—C1—C7—O1 | 178.84 (16) |
| O3—C2—C3—C11 | 5.0 (2) | C2—C1—C7—O2 | −179.73 (14) |
| C1—C2—C3—C11 | −174.17 (14) | C6—C1—C7—O2 | −1.0 (2) |
| C2—C3—C4—C5 | −2.3 (2) | C4—C3—C11—C12 | 125.94 (16) |
| C11—C3—C4—C5 | 175.72 (14) | C2—C3—C11—C12 | −56.1 (2) |
| C2—C3—C4—C9 | 176.59 (14) | C4—C3—C11—C16 | −54.8 (2) |
| C11—C3—C4—C9 | −5.4 (2) | C2—C3—C11—C16 | 123.15 (16) |
| C3—C4—C5—C6 | −0.2 (2) | C16—C11—C12—C13 | 1.0 (2) |
| C9—C4—C5—C6 | −179.04 (14) | C3—C11—C12—C13 | −179.75 (14) |
| C3—C4—C5—Cl1 | −178.97 (11) | C11—C12—C13—C14 | −0.6 (2) |
| C9—C4—C5—Cl1 | 2.1 (2) | C12—C13—C14—C15 | −0.5 (2) |
| C4—C5—C6—C1 | 1.0 (2) | C12—C13—C14—Cl2 | 179.39 (13) |
| Cl1—C5—C6—C1 | 179.78 (12) | C13—C14—C15—C16 | 1.2 (2) |
| C4—C5—C6—C10 | −179.32 (16) | Cl2—C14—C15—C16 | −178.73 (13) |
| Cl1—C5—C6—C10 | −0.5 (2) | C14—C15—C16—C11 | −0.8 (2) |
| C2—C1—C6—C5 | 0.6 (2) | C12—C11—C16—C15 | −0.3 (2) |
| C7—C1—C6—C5 | −178.07 (15) | C3—C11—C16—C15 | −179.57 (14) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3O···O1 | 0.77 (3) | 1.80 (3) | 2.523 (2) | 156 (3) |
| C12—H12···O3i | 0.95 | 2.53 | 3.306 (2) | 139 |
| C10—H10A···Cl1 | 0.98 | 2.45 | 3.029 (2) | 118 |
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