# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 Cl O4' _chemical_formula_weight 356.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.355(4) _cell_length_b 6.959(3) _cell_length_c 25.667(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.226(6) _cell_angle_gamma 90.00 _cell_volume 1666.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 4714 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 28.0 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9514 _exptl_absorpt_correction_T_max 0.9704 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.22 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17936 _diffrn_reflns_av_R_equivalents 0.0817 _diffrn_reflns_av_sigmaI/netI 0.0986 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3989 _reflns_number_gt 2797 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3989 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.16513(5) 0.43909(7) 0.034798(19) 0.03106(15) Uani 1 1 d . . . O1 O 0.68492(13) 0.07721(16) 0.20353(4) 0.0201(3) Uani 1 1 d . . . O2 O 0.71876(13) -0.12103(16) 0.13668(4) 0.0228(3) Uani 1 1 d . . . O3 O 0.98013(12) 0.11223(16) 0.13632(4) 0.0184(3) Uani 1 1 d . . . O4 O 1.09658(13) -0.03991(16) 0.07538(5) 0.0250(3) Uani 1 1 d . . . C1 C 0.73629(17) 0.2619(2) 0.21844(6) 0.0171(4) Uani 1 1 d . . . C2 C 0.69244(18) 0.3526(3) 0.26217(6) 0.0201(4) Uani 1 1 d . . . C3 C 0.74916(18) 0.5381(3) 0.27058(7) 0.0211(4) Uani 1 1 d . . . C4 C 0.84827(18) 0.6114(2) 0.23762(6) 0.0212(4) Uani 1 1 d . . . H4 H 0.8881 0.7347 0.2453 0.025 Uiso 1 1 calc R . . C5 C 0.89211(17) 0.5139(2) 0.19411(6) 0.0188(4) Uani 1 1 d . . . C6 C 0.83097(17) 0.3345(2) 0.18438(6) 0.0157(3) Uani 1 1 d . . . C7 C 0.83869(17) 0.1945(2) 0.14059(6) 0.0160(3) Uani 1 1 d . . . C8 C 0.74259(17) 0.0297(2) 0.15804(6) 0.0177(4) Uani 1 1 d . . . C9 C 0.59423(19) 0.2568(3) 0.29821(7) 0.0280(4) Uani 1 1 d . . . H9A H 0.5776 0.1233 0.2872 0.042 Uiso 1 1 calc R . . H9B H 0.5027 0.3257 0.2969 0.042 Uiso 1 1 calc R . . H9C H 0.6386 0.2591 0.3340 0.042 Uiso 1 1 calc R . . C10 C 0.70139(19) 0.6580(3) 0.31494(7) 0.0298(5) Uani 1 1 d . . . H10A H 0.7494 0.7832 0.3150 0.045 Uiso 1 1 calc R . . H10B H 0.7263 0.5922 0.3481 0.045 Uiso 1 1 calc R . . H10C H 0.5974 0.6766 0.3105 0.045 Uiso 1 1 calc R . . C11 C 0.99983(19) 0.6003(2) 0.15998(7) 0.0239(4) Uani 1 1 d . . . H11A H 1.0701 0.5023 0.1519 0.036 Uiso 1 1 calc R . . H11B H 1.0491 0.7075 0.1784 0.036 Uiso 1 1 calc R . . H11C H 0.9503 0.6472 0.1275 0.036 Uiso 1 1 calc R . . C12 C 0.99314(18) 0.0504(2) 0.08617(7) 0.0197(4) Uani 1 1 d . . . C13 C 0.86435(18) 0.1114(2) 0.05149(6) 0.0210(4) Uani 1 1 d . . . H13A H 0.7991 0.0016 0.0434 0.025 Uiso 1 1 calc R . . H13B H 0.8933 0.1671 0.0184 0.025 Uiso 1 1 calc R . . C14 C 0.79326(18) 0.2628(2) 0.08423(6) 0.0173(4) Uani 1 1 d . . . H14 H 0.8437 0.3872 0.0789 0.021 Uiso 1 1 calc R . . C15 C 0.63400(18) 0.3004(2) 0.07326(6) 0.0173(4) Uani 1 1 d . . . C16 C 0.58299(18) 0.4876(3) 0.07765(7) 0.0220(4) Uani 1 1 d . . . H16 H 0.6479 0.5875 0.0883 0.026 Uiso 1 1 calc R . . C17 C 0.43906(19) 0.5306(3) 0.06667(7) 0.0238(4) Uani 1 1 d . . . H17 H 0.4055 0.6586 0.0699 0.029 Uiso 1 1 calc R . . C18 C 0.34549(18) 0.3853(3) 0.05110(6) 0.0213(4) Uani 1 1 d . . . C19 C 0.39154(18) 0.1971(3) 0.04742(6) 0.0212(4) Uani 1 1 d . . . H19 H 0.3255 0.0975 0.0377 0.025 Uiso 1 1 calc R . . C20 C 0.53593(18) 0.1566(2) 0.05817(6) 0.0193(4) Uani 1 1 d . . . H20 H 0.5686 0.0281 0.0552 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0185(2) 0.0395(3) 0.0354(3) 0.0103(2) 0.0032(2) 0.00501(19) O1 0.0227(7) 0.0184(7) 0.0199(6) -0.0008(5) 0.0062(5) -0.0028(5) O2 0.0241(7) 0.0179(7) 0.0264(7) -0.0028(5) 0.0014(5) -0.0032(5) O3 0.0157(6) 0.0219(7) 0.0176(6) -0.0016(5) 0.0020(5) 0.0010(5) O4 0.0220(7) 0.0264(7) 0.0275(7) -0.0044(5) 0.0071(5) 0.0016(5) C1 0.0173(9) 0.0157(9) 0.0179(8) 0.0004(7) -0.0021(7) 0.0007(6) C2 0.0177(9) 0.0255(10) 0.0170(8) 0.0024(7) 0.0009(7) 0.0051(7) C3 0.0189(9) 0.0252(10) 0.0185(8) -0.0049(7) -0.0042(7) 0.0061(7) C4 0.0191(9) 0.0200(10) 0.0236(9) -0.0038(7) -0.0054(7) 0.0006(7) C5 0.0153(8) 0.0206(9) 0.0200(9) 0.0010(7) -0.0032(7) 0.0001(7) C6 0.0144(8) 0.0188(9) 0.0136(7) -0.0008(7) -0.0014(6) 0.0010(7) C7 0.0135(8) 0.0175(9) 0.0171(8) 0.0007(7) 0.0012(6) -0.0010(7) C8 0.0141(8) 0.0206(9) 0.0183(8) 0.0016(7) 0.0010(6) 0.0013(7) C9 0.0258(10) 0.0358(12) 0.0235(9) -0.0003(8) 0.0092(8) 0.0036(8) C10 0.0227(10) 0.0395(12) 0.0270(10) -0.0134(9) 0.0000(8) 0.0049(8) C11 0.0210(10) 0.0212(10) 0.0296(10) -0.0014(8) 0.0019(8) -0.0044(7) C12 0.0203(9) 0.0196(10) 0.0199(9) -0.0027(7) 0.0056(7) -0.0049(7) C13 0.0192(9) 0.0276(10) 0.0166(8) -0.0029(7) 0.0032(7) -0.0011(7) C14 0.0191(9) 0.0165(9) 0.0160(8) -0.0009(7) -0.0002(6) -0.0030(7) C15 0.0187(9) 0.0195(9) 0.0136(8) -0.0011(7) 0.0001(6) -0.0021(7) C16 0.0242(10) 0.0207(9) 0.0209(9) -0.0022(7) -0.0002(7) -0.0033(8) C17 0.0273(10) 0.0200(10) 0.0241(9) -0.0003(7) 0.0019(8) 0.0042(8) C18 0.0160(9) 0.0308(11) 0.0171(8) 0.0038(7) 0.0020(7) 0.0032(7) C19 0.0187(9) 0.0255(10) 0.0191(8) -0.0015(7) -0.0003(7) -0.0037(7) C20 0.0210(9) 0.0185(9) 0.0183(8) -0.0004(7) 0.0010(7) 0.0005(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C18 1.7488(18) . ? O1 C8 1.3627(19) . ? O1 C1 1.4152(19) . ? O2 C8 1.1966(19) . ? O3 C12 1.3712(19) . ? O3 C7 1.4533(19) . ? O4 C12 1.2033(19) . ? C1 C2 1.376(2) . ? C1 C6 1.385(2) . ? C2 C3 1.406(2) . ? C2 C9 1.507(2) . ? C3 C4 1.397(2) . ? C3 C10 1.506(2) . ? C4 C5 1.394(2) . ? C4 H4 0.9500 . ? C5 C6 1.388(2) . ? C5 C11 1.508(2) . ? C6 C7 1.493(2) . ? C7 C8 1.544(2) . ? C7 C14 1.552(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.505(2) . ? C13 C14 1.530(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.519(2) . ? C14 H14 1.0000 . ? C15 C20 1.393(2) . ? C15 C16 1.395(2) . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 C18 1.377(2) . ? C17 H17 0.9500 . ? C18 C19 1.384(2) . ? C19 C20 1.388(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 C1 107.71(12) . . ? C12 O3 C7 109.79(12) . . ? C2 C1 C6 126.20(16) . . ? C2 C1 O1 121.42(15) . . ? C6 C1 O1 112.38(14) . . ? C1 C2 C3 114.47(16) . . ? C1 C2 C9 122.00(16) . . ? C3 C2 C9 123.53(16) . . ? C4 C3 C2 120.14(16) . . ? C4 C3 C10 120.20(16) . . ? C2 C3 C10 119.66(16) . . ? C5 C4 C3 123.72(16) . . ? C5 C4 H4 118.1 . . ? C3 C4 H4 118.1 . . ? C6 C5 C4 116.11(16) . . ? C6 C5 C11 122.54(15) . . ? C4 C5 C11 121.35(15) . . ? C1 C6 C5 119.25(15) . . ? C1 C6 C7 107.82(14) . . ? C5 C6 C7 132.84(15) . . ? O3 C7 C6 114.12(13) . . ? O3 C7 C8 106.37(13) . . ? C6 C7 C8 101.82(13) . . ? O3 C7 C14 103.81(12) . . ? C6 C7 C14 118.48(14) . . ? C8 C7 C14 111.87(13) . . ? O2 C8 O1 122.22(15) . . ? O2 C8 C7 127.66(15) . . ? O1 C8 C7 110.11(14) . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O4 C12 O3 120.55(16) . . ? O4 C12 C13 129.31(16) . . ? O3 C12 C13 110.13(14) . . ? C12 C13 C14 103.34(13) . . ? C12 C13 H13A 111.1 . . ? C14 C13 H13A 111.1 . . ? C12 C13 H13B 111.1 . . ? C14 C13 H13B 111.1 . . ? H13A C13 H13B 109.1 . . ? C15 C14 C13 118.51(14) . . ? C15 C14 C7 115.03(13) . . ? C13 C14 C7 101.59(13) . . ? C15 C14 H14 107.0 . . ? C13 C14 H14 107.0 . . ? C7 C14 H14 107.0 . . ? C20 C15 C16 118.11(16) . . ? C20 C15 C14 123.00(15) . . ? C16 C15 C14 118.88(15) . . ? C17 C16 C15 121.15(16) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C18 C17 C16 119.17(17) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 121.33(16) . . ? C17 C18 Cl1 119.59(14) . . ? C19 C18 Cl1 119.07(13) . . ? C18 C19 C20 118.83(16) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C19 C20 C15 121.38(16) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O1 C1 C2 177.59(15) . . . . ? C8 O1 C1 C6 -2.05(18) . . . . ? C6 C1 C2 C3 1.8(3) . . . . ? O1 C1 C2 C3 -177.79(14) . . . . ? C6 C1 C2 C9 -176.95(16) . . . . ? O1 C1 C2 C9 3.5(2) . . . . ? C1 C2 C3 C4 -3.7(2) . . . . ? C9 C2 C3 C4 175.04(16) . . . . ? C1 C2 C3 C10 175.69(15) . . . . ? C9 C2 C3 C10 -5.6(3) . . . . ? C2 C3 C4 C5 2.9(3) . . . . ? C10 C3 C4 C5 -176.44(15) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C3 C4 C5 C11 -179.88(16) . . . . ? C2 C1 C6 C5 1.1(3) . . . . ? O1 C1 C6 C5 -179.24(13) . . . . ? C2 C1 C6 C7 -175.79(15) . . . . ? O1 C1 C6 C7 3.83(18) . . . . ? C4 C5 C6 C1 -2.1(2) . . . . ? C11 C5 C6 C1 177.91(16) . . . . ? C4 C5 C6 C7 173.94(16) . . . . ? C11 C5 C6 C7 -6.1(3) . . . . ? C12 O3 C7 C6 -156.17(13) . . . . ? C12 O3 C7 C8 92.40(14) . . . . ? C12 O3 C7 C14 -25.77(16) . . . . ? C1 C6 C7 O3 -117.93(15) . . . . ? C5 C6 C7 O3 65.7(2) . . . . ? C1 C6 C7 C8 -3.78(17) . . . . ? C5 C6 C7 C8 179.88(17) . . . . ? C1 C6 C7 C14 119.35(16) . . . . ? C5 C6 C7 C14 -57.0(2) . . . . ? C1 O1 C8 O2 179.04(15) . . . . ? C1 O1 C8 C7 -0.57(17) . . . . ? O3 C7 C8 O2 -57.1(2) . . . . ? C6 C7 C8 O2 -176.91(17) . . . . ? C14 C7 C8 O2 55.6(2) . . . . ? O3 C7 C8 O1 122.46(13) . . . . ? C6 C7 C8 O1 2.68(17) . . . . ? C14 C7 C8 O1 -124.84(14) . . . . ? C7 O3 C12 O4 -172.43(15) . . . . ? C7 O3 C12 C13 7.13(18) . . . . ? O4 C12 C13 C14 -165.70(17) . . . . ? O3 C12 C13 C14 14.79(18) . . . . ? C12 C13 C14 C15 -155.77(14) . . . . ? C12 C13 C14 C7 -28.69(16) . . . . ? O3 C7 C14 C15 162.53(13) . . . . ? C6 C7 C14 C15 -69.72(19) . . . . ? C8 C7 C14 C15 48.24(19) . . . . ? O3 C7 C14 C13 33.23(15) . . . . ? C6 C7 C14 C13 160.97(14) . . . . ? C8 C7 C14 C13 -81.07(15) . . . . ? C13 C14 C15 C20 35.1(2) . . . . ? C7 C14 C15 C20 -85.34(19) . . . . ? C13 C14 C15 C16 -143.95(15) . . . . ? C7 C14 C15 C16 95.65(18) . . . . ? C20 C15 C16 C17 -0.8(3) . . . . ? C14 C15 C16 C17 178.22(14) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C16 C17 C18 C19 1.6(3) . . . . ? C16 C17 C18 Cl1 -177.62(13) . . . . ? C17 C18 C19 C20 -2.0(3) . . . . ? Cl1 C18 C19 C20 177.18(12) . . . . ? C18 C19 C20 C15 1.0(2) . . . . ? C16 C15 C20 C19 0.4(2) . . . . ? C14 C15 C20 C19 -178.63(15) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.416 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.111 _database_code_depnum_ccdc_archive 'CCDC 938657' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_m130415a1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 Cl O4' _chemical_formula_weight 356.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.874(6) _cell_length_b 14.457(7) _cell_length_c 10.519(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.210(8) _cell_angle_gamma 90.00 _cell_volume 1715.3(14) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 6443 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9527 _exptl_absorpt_correction_T_max 0.9712 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.22 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15684 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.90 _reflns_number_total 4090 _reflns_number_gt 2892 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4090 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.23749(3) 1.01365(3) 0.39375(3) 0.03125(11) Uani 1 1 d . . . O1 O -0.07319(8) 0.77031(6) 1.03512(8) 0.0227(2) Uani 1 1 d . . . O2 O 0.09554(7) 0.84870(6) 1.06515(8) 0.0177(2) Uani 1 1 d . . . O3 O 0.23505(7) 0.82109(6) 0.95725(8) 0.0170(2) Uani 1 1 d . . . O4 O 0.19944(8) 1.03962(6) 1.08863(8) 0.0209(2) Uani 1 1 d . . . C1 C -0.01055(11) 0.81130(9) 0.98511(12) 0.0175(3) Uani 1 1 d . . . C2 C -0.02459(11) 0.83328(9) 0.84147(11) 0.0180(3) Uani 1 1 d . . . H2A H -0.1074 0.8505 0.7919 0.022 Uiso 1 1 calc R . . H2B H -0.0007 0.7803 0.7961 0.022 Uiso 1 1 calc R . . C3 C 0.05968(10) 0.91559(9) 0.85369(11) 0.0150(3) Uani 1 1 d . . . H3 H 0.0188 0.9717 0.8735 0.018 Uiso 1 1 calc R . . C4 C 0.15710(11) 0.88937(9) 0.98219(11) 0.0157(3) Uani 1 1 d . . . C5 C 0.23801(11) 0.96723(9) 1.06178(11) 0.0157(3) Uani 1 1 d . . . C6 C 0.35806(11) 0.93279(9) 1.08783(12) 0.0176(3) Uani 1 1 d . . . C7 C 0.46878(12) 0.96966(10) 1.16017(12) 0.0220(3) Uani 1 1 d . . . C8 C 0.56679(12) 0.91804(11) 1.15775(14) 0.0281(3) Uani 1 1 d . . . H8 H 0.6434 0.9401 1.2068 0.034 Uiso 1 1 calc R . . C9 C 0.55823(12) 0.83539(11) 1.08673(14) 0.0270(3) Uani 1 1 d . . . C10 C 0.44726(11) 0.79841(10) 1.01317(12) 0.0217(3) Uani 1 1 d . . . C11 C 0.35063(11) 0.84944(9) 1.02027(11) 0.0170(3) Uani 1 1 d . . . C12 C 0.43329(12) 0.71228(10) 0.92934(14) 0.0283(3) Uani 1 1 d . . . H12A H 0.3493 0.7031 0.8794 0.042 Uiso 1 1 calc R . . H12B H 0.4628 0.6589 0.9876 0.042 Uiso 1 1 calc R . . H12C H 0.4787 0.7188 0.8664 0.042 Uiso 1 1 calc R . . C13 C 0.67055(12) 0.78512(12) 1.08868(17) 0.0421(4) Uani 1 1 d . . . H13A H 0.6640 0.7198 1.1102 0.063 Uiso 1 1 calc R . . H13B H 0.7384 0.8129 1.1565 0.063 Uiso 1 1 calc R . . H13C H 0.6819 0.7901 1.0006 0.063 Uiso 1 1 calc R . . C14 C 0.48026(13) 1.05835(11) 1.23793(14) 0.0303(3) Uani 1 1 d . . . H14A H 0.4668 1.0461 1.3237 0.045 Uiso 1 1 calc R . . H14B H 0.4214 1.1030 1.1866 0.045 Uiso 1 1 calc R . . H14C H 0.5600 1.0838 1.2542 0.045 Uiso 1 1 calc R . . C15 C 0.10264(10) 0.93868(9) 0.73684(11) 0.0148(3) Uani 1 1 d . . . C16 C 0.14820(11) 0.87111(9) 0.67186(11) 0.0178(3) Uani 1 1 d . . . H16 H 0.1511 0.8085 0.7003 0.021 Uiso 1 1 calc R . . C17 C 0.18922(11) 0.89419(10) 0.56641(12) 0.0196(3) Uani 1 1 d . . . H17 H 0.2198 0.8479 0.5221 0.024 Uiso 1 1 calc R . . C18 C 0.18514(11) 0.98568(10) 0.52633(12) 0.0192(3) Uani 1 1 d . . . C19 C 0.13973(11) 1.05417(9) 0.58743(12) 0.0192(3) Uani 1 1 d . . . H19 H 0.1368 1.1165 0.5582 0.023 Uiso 1 1 calc R . . C20 C 0.09822(11) 1.02992(9) 0.69306(12) 0.0173(3) Uani 1 1 d . . . H20 H 0.0664 1.0764 0.7359 0.021 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0378(2) 0.0352(2) 0.02762(19) 0.01033(15) 0.02011(17) 0.00513(17) O1 0.0201(5) 0.0203(5) 0.0309(5) 0.0045(4) 0.0126(4) -0.0011(4) O2 0.0163(5) 0.0200(5) 0.0179(4) 0.0028(4) 0.0068(4) -0.0021(4) O3 0.0143(5) 0.0154(5) 0.0211(4) -0.0010(3) 0.0054(4) 0.0010(4) O4 0.0227(5) 0.0196(5) 0.0217(5) -0.0035(4) 0.0088(4) 0.0000(4) C1 0.0167(7) 0.0123(7) 0.0246(7) 0.0000(5) 0.0081(6) 0.0028(5) C2 0.0160(7) 0.0181(7) 0.0202(6) -0.0019(5) 0.0062(5) -0.0010(5) C3 0.0142(6) 0.0139(7) 0.0171(6) -0.0003(5) 0.0051(5) 0.0005(5) C4 0.0161(6) 0.0152(7) 0.0176(6) -0.0001(5) 0.0079(5) 0.0000(5) C5 0.0176(7) 0.0192(7) 0.0114(5) 0.0020(5) 0.0060(5) -0.0021(5) C6 0.0152(7) 0.0210(7) 0.0165(6) 0.0017(5) 0.0051(5) -0.0014(5) C7 0.0185(7) 0.0271(8) 0.0201(7) 0.0017(6) 0.0056(6) -0.0043(6) C8 0.0150(7) 0.0372(10) 0.0296(8) 0.0026(6) 0.0034(6) -0.0031(6) C9 0.0168(7) 0.0331(9) 0.0323(8) 0.0067(6) 0.0093(6) 0.0045(6) C10 0.0208(7) 0.0219(8) 0.0253(7) 0.0051(5) 0.0114(6) 0.0041(6) C11 0.0138(6) 0.0213(7) 0.0152(6) 0.0041(5) 0.0037(5) 0.0001(5) C12 0.0278(8) 0.0240(9) 0.0371(8) 0.0019(6) 0.0161(7) 0.0055(6) C13 0.0199(8) 0.0431(11) 0.0634(11) 0.0011(9) 0.0132(8) 0.0075(7) C14 0.0236(8) 0.0360(9) 0.0289(7) -0.0080(6) 0.0048(6) -0.0098(7) C15 0.0118(6) 0.0173(7) 0.0140(6) -0.0010(5) 0.0020(5) -0.0015(5) C16 0.0192(7) 0.0151(7) 0.0182(6) -0.0007(5) 0.0048(5) -0.0010(5) C17 0.0194(7) 0.0210(7) 0.0184(6) -0.0023(5) 0.0059(5) 0.0011(5) C18 0.0166(7) 0.0268(8) 0.0144(6) 0.0029(5) 0.0050(5) -0.0009(6) C19 0.0178(7) 0.0169(7) 0.0210(6) 0.0037(5) 0.0031(5) -0.0004(5) C20 0.0146(6) 0.0178(7) 0.0183(6) -0.0007(5) 0.0032(5) 0.0009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C18 1.7426(14) . ? O1 C1 1.1940(15) . ? O2 C1 1.3875(15) . ? O2 C4 1.4284(15) . ? O3 C11 1.3864(15) . ? O3 C4 1.4324(15) . ? O4 C5 1.2107(16) . ? C1 C2 1.5014(18) . ? C2 C3 1.5340(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C15 1.5081(17) . ? C3 C4 1.5270(17) . ? C3 H3 1.0000 . ? C4 C5 1.5455(18) . ? C5 C6 1.4528(18) . ? C6 C11 1.3876(19) . ? C6 C7 1.4022(18) . ? C7 C8 1.389(2) . ? C7 C14 1.504(2) . ? C8 C9 1.396(2) . ? C8 H8 0.9500 . ? C9 C10 1.408(2) . ? C9 C13 1.5133(19) . ? C10 C11 1.3855(18) . ? C10 C12 1.505(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C20 1.3926(18) . ? C15 C16 1.3948(17) . ? C16 C17 1.3844(18) . ? C16 H16 0.9500 . ? C17 C18 1.3845(19) . ? C17 H17 0.9500 . ? C18 C19 1.3786(18) . ? C19 C20 1.3938(18) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C4 109.30(9) . . ? C11 O3 C4 107.97(10) . . ? O1 C1 O2 119.90(11) . . ? O1 C1 C2 131.29(12) . . ? O2 C1 C2 108.81(10) . . ? C1 C2 C3 102.44(10) . . ? C1 C2 H2A 111.3 . . ? C3 C2 H2A 111.3 . . ? C1 C2 H2B 111.3 . . ? C3 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? C15 C3 C4 114.89(11) . . ? C15 C3 C2 118.78(10) . . ? C4 C3 C2 100.11(10) . . ? C15 C3 H3 107.5 . . ? C4 C3 H3 107.5 . . ? C2 C3 H3 107.5 . . ? O2 C4 O3 108.15(10) . . ? O2 C4 C3 104.62(10) . . ? O3 C4 C3 111.29(10) . . ? O2 C4 C5 108.60(9) . . ? O3 C4 C5 105.86(10) . . ? C3 C4 C5 118.00(11) . . ? O4 C5 C6 132.28(12) . . ? O4 C5 C4 122.65(11) . . ? C6 C5 C4 105.05(11) . . ? C11 C6 C7 120.45(12) . . ? C11 C6 C5 107.42(11) . . ? C7 C6 C5 132.09(13) . . ? C8 C7 C6 115.75(13) . . ? C8 C7 C14 122.27(13) . . ? C6 C7 C14 121.97(13) . . ? C7 C8 C9 123.25(13) . . ? C7 C8 H8 118.4 . . ? C9 C8 H8 118.4 . . ? C8 C9 C10 121.20(13) . . ? C8 C9 C13 119.17(13) . . ? C10 C9 C13 119.63(14) . . ? C11 C10 C9 114.62(13) . . ? C11 C10 C12 122.06(12) . . ? C9 C10 C12 123.29(12) . . ? C10 C11 O3 121.97(12) . . ? C10 C11 C6 124.67(12) . . ? O3 C11 C6 113.36(11) . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 118.79(11) . . ? C20 C15 C3 119.46(11) . . ? C16 C15 C3 121.74(12) . . ? C17 C16 C15 120.75(12) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 119.12(12) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C19 C18 C17 121.72(12) . . ? C19 C18 Cl1 119.72(11) . . ? C17 C18 Cl1 118.56(10) . . ? C18 C19 C20 118.57(12) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C15 C20 C19 121.04(12) . . ? C15 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O2 C1 O1 176.76(11) . . . . ? C4 O2 C1 C2 -3.77(13) . . . . ? O1 C1 C2 C3 159.16(14) . . . . ? O2 C1 C2 C3 -20.23(13) . . . . ? C1 C2 C3 C15 159.91(10) . . . . ? C1 C2 C3 C4 34.07(12) . . . . ? C1 O2 C4 O3 -92.14(11) . . . . ? C1 O2 C4 C3 26.57(12) . . . . ? C1 O2 C4 C5 153.42(10) . . . . ? C11 O3 C4 O2 -112.95(10) . . . . ? C11 O3 C4 C3 132.67(10) . . . . ? C11 O3 C4 C5 3.29(12) . . . . ? C15 C3 C4 O2 -165.79(10) . . . . ? C2 C3 C4 O2 -37.35(11) . . . . ? C15 C3 C4 O3 -49.23(14) . . . . ? C2 C3 C4 O3 79.22(12) . . . . ? C15 C3 C4 C5 73.41(14) . . . . ? C2 C3 C4 C5 -158.15(10) . . . . ? O2 C4 C5 O4 -70.83(14) . . . . ? O3 C4 C5 O4 173.23(10) . . . . ? C3 C4 C5 O4 47.89(16) . . . . ? O2 C4 C5 C6 110.47(10) . . . . ? O3 C4 C5 C6 -5.47(12) . . . . ? C3 C4 C5 C6 -130.81(11) . . . . ? O4 C5 C6 C11 -172.91(13) . . . . ? C4 C5 C6 C11 5.61(12) . . . . ? O4 C5 C6 C7 4.8(2) . . . . ? C4 C5 C6 C7 -176.72(13) . . . . ? C11 C6 C7 C8 0.48(18) . . . . ? C5 C6 C7 C8 -176.94(13) . . . . ? C11 C6 C7 C14 -178.16(12) . . . . ? C5 C6 C7 C14 4.4(2) . . . . ? C6 C7 C8 C9 1.1(2) . . . . ? C14 C7 C8 C9 179.74(13) . . . . ? C7 C8 C9 C10 -0.7(2) . . . . ? C7 C8 C9 C13 179.00(13) . . . . ? C8 C9 C10 C11 -1.23(19) . . . . ? C13 C9 C10 C11 179.04(13) . . . . ? C8 C9 C10 C12 176.76(13) . . . . ? C13 C9 C10 C12 -3.0(2) . . . . ? C9 C10 C11 O3 -177.86(11) . . . . ? C12 C10 C11 O3 4.11(19) . . . . ? C9 C10 C11 C6 2.92(19) . . . . ? C12 C10 C11 C6 -175.11(12) . . . . ? C4 O3 C11 C10 -179.05(11) . . . . ? C4 O3 C11 C6 0.25(13) . . . . ? C7 C6 C11 C10 -2.64(19) . . . . ? C5 C6 C11 C10 175.35(11) . . . . ? C7 C6 C11 O3 178.09(10) . . . . ? C5 C6 C11 O3 -3.92(14) . . . . ? C4 C3 C15 C20 -109.27(13) . . . . ? C2 C3 C15 C20 132.34(12) . . . . ? C4 C3 C15 C16 69.99(15) . . . . ? C2 C3 C15 C16 -48.40(16) . . . . ? C20 C15 C16 C17 0.50(18) . . . . ? C3 C15 C16 C17 -178.77(11) . . . . ? C15 C16 C17 C18 0.36(19) . . . . ? C16 C17 C18 C19 -0.96(19) . . . . ? C16 C17 C18 Cl1 179.82(9) . . . . ? C17 C18 C19 C20 0.66(19) . . . . ? Cl1 C18 C19 C20 179.87(10) . . . . ? C16 C15 C20 C19 -0.81(18) . . . . ? C3 C15 C20 C19 178.48(11) . . . . ? C18 C19 C20 C15 0.24(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.261 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 938658'