# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Reiko Kuroda' _publ_contact_author_email CKURODA@MAIL.ECC.U-TOKYO.AC.JP _publ_section_title ; Supramolecular chirality measured by diffuse reflectance circular dichroism spectroscopy ; loop_ _publ_author_name 'Reiko Kuroda' 'Natsuyo Asano' 'Takunori Harada' 'Tomohiro Sato' 'Nobuo Tajima' # Attachment 'ASANO81.CIF' data_qpyri _database_code_depnum_ccdc_archive 'CCDC 703676' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H14 O2' _chemical_formula_weight 310.33 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 7.59530(10) _cell_length_b 7.59530(10) _cell_length_c 25.2629(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1457.38(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1828 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 28.27 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9565 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10807 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1846 _reflns_number_gt 1828 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0885P)^2^+0.4233P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 1846 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.001 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 C1 C -0.0729(3) 1.0919(3) 0.96108(9) 0.0216(5) Uani 1 1 d . . . C2 C -0.0715(3) 0.9969(4) 1.01227(10) 0.0238(5) Uani 1 1 d . . . H2 H -0.1176 1.0532 1.0429 0.029 Uiso 1 1 calc R . . C3 C -0.0072(4) 0.8350(4) 1.01639(10) 0.0255(5) Uani 1 1 d . . . H3 H -0.0083 0.7788 1.0500 0.031 Uiso 1 1 calc R . . C4 C 0.0669(3) 0.7384(4) 0.96997(11) 0.0254(5) Uani 1 1 d . . . C5 C 0.0667(3) 0.8362(4) 0.91909(10) 0.0243(5) Uani 1 1 d . . . H5 H 0.1139 0.7810 0.8885 0.029 Uiso 1 1 calc R . . C6 C 0.0027(4) 0.9981(4) 0.91500(10) 0.0228(5) Uani 1 1 d . . . H6 H 0.0054 1.0555 0.8816 0.027 Uiso 1 1 calc R . . O1 O -0.1327(3) 1.2353(2) 0.95791(8) 0.0272(4) Uani 1 1 d . . . O4 O 0.1225(3) 0.5936(3) 0.97361(10) 0.0345(5) Uani 1 1 d . . . C11 C 0.6581(3) 0.6367(3) 0.90016(9) 0.0174(4) Uani 1 1 d . . . H11 H 0.7060 0.5217 0.9033 0.021 Uiso 1 1 calc R . . C12 C 0.6561(3) 0.7199(3) 0.85096(9) 0.0177(4) Uani 1 1 d . . . H12 H 0.7027 0.6607 0.8209 0.021 Uiso 1 1 calc R . . C13 C 0.5870(3) 0.8880(3) 0.84531(8) 0.0170(4) Uani 1 1 d . . . H13 H 0.5861 0.9426 0.8115 0.020 Uiso 1 1 calc R . . C14 C 0.5183(3) 0.9781(3) 0.88944(8) 0.0153(4) Uani 1 1 d . . . C15 C 0.4529(3) 0.9829(3) 0.98513(8) 0.0140(4) Uani 1 1 d . . . C16 C 0.4557(3) 0.8988(3) 1.03560(9) 0.0151(4) Uani 1 1 d . . . C17 C 0.5273(3) 0.7236(3) 1.03942(9) 0.0170(4) Uani 1 1 d . . . H17 H 0.5300 0.6663 1.0728 0.020 Uiso 1 1 calc R . . C18 C 0.5908(3) 0.6392(3) 0.99632(9) 0.0170(4) Uani 1 1 d . . . H18 H 0.6366 0.5235 1.0000 0.020 Uiso 1 1 calc R . . C19 C 0.5903(3) 0.7214(3) 0.94493(9) 0.0157(4) Uani 1 1 d . . . C20 C 0.5207(3) 0.8941(3) 0.93986(8) 0.0141(4) Uani 1 1 d . . . C21 C 0.4471(3) 1.1535(3) 0.88562(9) 0.0171(4) Uani 1 1 d . . . H21 H 0.4451 1.2112 0.8523 0.021 Uiso 1 1 calc R . . C22 C 0.3831(3) 1.2375(3) 0.92883(9) 0.0168(4) Uani 1 1 d . . . H22 H 0.3376 1.3534 0.9252 0.020 Uiso 1 1 calc R . . C23 C 0.3824(3) 1.1551(3) 0.97996(8) 0.0147(4) Uani 1 1 d . . . C24 C 0.3132(3) 1.2393(3) 1.02458(9) 0.0160(4) Uani 1 1 d . . . H24 H 0.2635 1.3536 1.0213 0.019 Uiso 1 1 calc R . . C25 C 0.3168(3) 1.1566(3) 1.07384(9) 0.0170(4) Uani 1 1 d . . . H25 H 0.2700 1.2153 1.1039 0.020 Uiso 1 1 calc R . . C26 C 0.3882(3) 0.9888(3) 1.07941(8) 0.0164(4) Uani 1 1 d . . . H26 H 0.3911 0.9348 1.1133 0.020 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 C1 0.0224(11) 0.0243(11) 0.0181(11) 0.0031(9) -0.0057(8) -0.0040(8) C2 0.0255(12) 0.0260(12) 0.0201(11) -0.0006(9) -0.0009(9) -0.0024(9) C3 0.0289(12) 0.0278(13) 0.0198(11) 0.0052(10) -0.0039(10) -0.0050(10) C4 0.0199(11) 0.0317(13) 0.0246(12) 0.0072(10) -0.0068(9) -0.0063(9) C5 0.0254(12) 0.0266(12) 0.0210(12) 0.0003(9) -0.0010(9) -0.0027(9) C6 0.0261(12) 0.0229(11) 0.0195(11) 0.0020(8) -0.0022(9) -0.0021(9) O1 0.0298(9) 0.0245(9) 0.0272(9) -0.0089(7) -0.0002(7) -0.0001(7) O4 0.0374(11) 0.0285(10) 0.0377(11) -0.0009(9) -0.0021(9) 0.0028(8) C11 0.0176(10) 0.0142(9) 0.0204(11) -0.0023(8) 0.0005(8) -0.0002(8) C12 0.0182(10) 0.0194(10) 0.0155(9) -0.0033(8) 0.0005(8) -0.0009(8) C13 0.0186(10) 0.0177(10) 0.0147(10) 0.0023(8) -0.0002(8) -0.0017(8) C14 0.0153(10) 0.0147(10) 0.0160(11) 0.0009(8) 0.0003(7) -0.0008(7) C15 0.0147(9) 0.0150(9) 0.0124(9) 0.0004(7) -0.0002(7) -0.0007(7) C16 0.0138(9) 0.0159(10) 0.0154(10) 0.0025(8) -0.0020(7) 0.0002(7) C17 0.0173(10) 0.0158(10) 0.0179(10) 0.0063(8) -0.0007(8) 0.0002(8) C18 0.0185(10) 0.0152(10) 0.0173(10) 0.0051(8) -0.0013(8) 0.0018(7) C19 0.0151(10) 0.0150(9) 0.0169(10) 0.0010(8) 0.0000(7) -0.0004(7) C20 0.0138(9) 0.0137(9) 0.0147(10) -0.0001(7) -0.0006(7) -0.0014(7) C21 0.0182(10) 0.0171(10) 0.0161(10) 0.0054(8) -0.0027(8) -0.0008(8) C22 0.0171(10) 0.0133(9) 0.0200(10) 0.0022(8) -0.0015(8) -0.0008(7) C23 0.0145(10) 0.0141(9) 0.0157(10) 0.0001(8) -0.0019(7) -0.0019(7) C24 0.0166(10) 0.0145(9) 0.0168(10) -0.0003(8) -0.0019(8) 0.0002(7) C25 0.0173(10) 0.0173(10) 0.0163(10) -0.0026(8) 0.0014(8) -0.0011(7) C26 0.0183(10) 0.0197(10) 0.0112(10) 0.0026(7) 0.0001(8) -0.0006(8) _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 C1 O1 1.183(3) . ? C1 C6 1.481(3) . ? C1 C2 1.481(3) . ? C2 C3 1.327(4) . ? C3 C4 1.494(4) . ? C4 O4 1.182(3) . ? C4 C5 1.485(4) . ? C5 C6 1.327(4) . ? C11 C12 1.394(3) . ? C11 C19 1.399(3) . ? C12 C13 1.388(3) . ? C13 C14 1.408(3) . ? C14 C20 1.425(3) . ? C14 C21 1.441(3) . ? C15 C23 1.419(3) . ? C15 C20 1.424(3) . ? C15 C16 1.426(3) . ? C16 C26 1.398(3) . ? C16 C17 1.441(3) . ? C17 C18 1.352(3) . ? C18 C19 1.440(3) . ? C19 C20 1.420(3) . ? C21 C22 1.355(3) . ? C22 C23 1.435(3) . ? C23 C24 1.399(3) . ? C24 C25 1.394(3) . ? C25 C26 1.393(3) . ? 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 O1 C1 C6 122.6(2) . . ? O1 C1 C2 120.7(2) . . ? C6 C1 C2 116.7(2) . . ? C3 C2 C1 121.5(2) . . ? C2 C3 C4 122.2(2) . . ? O4 C4 C5 122.2(3) . . ? O4 C4 C3 122.1(3) . . ? C5 C4 C3 115.7(2) . . ? C6 C5 C4 122.1(2) . . ? C5 C6 C1 121.8(2) . . ? C12 C11 C19 120.6(2) . . ? C13 C12 C11 120.8(2) . . ? C12 C13 C14 120.4(2) . . ? C13 C14 C20 119.02(19) . . ? C13 C14 C21 122.4(2) . . ? C20 C14 C21 118.59(19) . . ? C23 C15 C20 119.92(19) . . ? C23 C15 C16 120.04(19) . . ? C20 C15 C16 120.04(18) . . ? C26 C16 C15 118.91(19) . . ? C26 C16 C17 122.5(2) . . ? C15 C16 C17 118.63(19) . . ? C18 C17 C16 121.2(2) . . ? C17 C18 C19 121.30(19) . . ? C11 C19 C20 119.2(2) . . ? C11 C19 C18 121.9(2) . . ? C20 C19 C18 118.9(2) . . ? C19 C20 C15 119.96(19) . . ? C19 C20 C14 119.94(19) . . ? C15 C20 C14 120.09(18) . . ? C22 C21 C14 121.1(2) . . ? C21 C22 C23 121.41(19) . . ? C24 C23 C15 119.3(2) . . ? C24 C23 C22 121.82(19) . . ? C15 C23 C22 118.90(19) . . ? C25 C24 C23 120.4(2) . . ? C26 C25 C24 120.7(2) . . ? C25 C26 C16 120.67(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.477 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.055 #===END data_2cqp22b _database_code_depnum_ccdc_archive 'CCDC 703677' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H13 Cl O2' _chemical_formula_weight 344.77 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 Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 7.5714(3) _cell_length_b 7.5714(3) _cell_length_c 26.8898(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1541.49(13) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2983 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 27.87 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9029 _exptl_absorpt_correction_T_max 0.9497 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9601 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3138 _reflns_number_gt 2983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0960P)^2^+0.7312P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(9) _refine_ls_number_reflns 3138 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1430 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _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 C1 C 0.2498(4) 0.9824(4) 0.82362(13) 0.0322(7) Uani 1 1 d . . . C2 C 0.1674(5) 0.9737(4) 0.87387(13) 0.0326(7) Uani 1 1 d . . . C3 C 0.0074(5) 1.0318(4) 0.88299(14) 0.0357(7) Uani 1 1 d . . . H3 H -0.0395 1.0225 0.9156 0.043 Uiso 1 1 calc R . . C4 C -0.1002(5) 1.1110(5) 0.84337(16) 0.0415(9) Uani 1 1 d . . . C5 C -0.0210(5) 1.1224(5) 0.79232(15) 0.0401(8) Uani 1 1 d . . . H5 H -0.0869 1.1727 0.7658 0.048 Uiso 1 1 calc R . . C6 C 0.1407(5) 1.0623(5) 0.78428(14) 0.0384(7) Uani 1 1 d . . . H6 H 0.1885 1.0711 0.7517 0.046 Uiso 1 1 calc R . . O1 O 0.3951(3) 0.9261(4) 0.81567(11) 0.0445(6) Uani 1 1 d . . . O4 O -0.2504(3) 1.1556(3) 0.85269(11) 0.0404(6) Uani 1 1 d . . . Cl2 Cl 0.29589(11) 0.88212(11) 0.91944(4) 0.0391(2) Uani 1 1 d . . . C11 C 0.1249(4) 1.4286(4) 0.95419(11) 0.0254(6) Uani 1 1 d . . . H11 H 0.0713 1.4269 0.9861 0.031 Uiso 1 1 calc R . . C12 C 0.2947(4) 1.3628(4) 0.94829(12) 0.0257(6) Uani 1 1 d . . . H12 H 0.3558 1.3154 0.9761 0.031 Uiso 1 1 calc R . . C13 C 0.3760(4) 1.3656(4) 0.90199(11) 0.0241(6) Uani 1 1 d . . . H13 H 0.4925 1.3206 0.8985 0.029 Uiso 1 1 calc R . . C14 C 0.2888(3) 1.4337(3) 0.86052(11) 0.0206(5) Uani 1 1 d . . . C15 C 0.0231(3) 1.5711(3) 0.82424(11) 0.0201(5) Uani 1 1 d . . . C16 C -0.1525(3) 1.6369(4) 0.82984(11) 0.0225(6) Uani 1 1 d . . . C17 C -0.2318(4) 1.6328(4) 0.87809(12) 0.0257(6) Uani 1 1 d . . . H17 H -0.3485 1.6765 0.8822 0.031 Uiso 1 1 calc R . . C18 C -0.1445(4) 1.5683(4) 0.91774(13) 0.0264(6) Uani 1 1 d . . . H18 H -0.2003 1.5692 0.9494 0.032 Uiso 1 1 calc R . . C19 C 0.0312(3) 1.4980(3) 0.91331(11) 0.0218(6) Uani 1 1 d . . . C20 C 0.1139(3) 1.5010(3) 0.86601(10) 0.0193(5) Uani 1 1 d . . . C21 C 0.3692(3) 1.4395(3) 0.81207(12) 0.0225(6) Uani 1 1 d . . . H21 H 0.4853 1.3944 0.8078 0.027 Uiso 1 1 calc R . . C22 C 0.2833(4) 1.5079(3) 0.77256(11) 0.0235(6) Uani 1 1 d . . . H22 H 0.3405 1.5106 0.7411 0.028 Uiso 1 1 calc R . . C23 C 0.1062(3) 1.5770(3) 0.77704(11) 0.0208(5) Uani 1 1 d . . . C24 C 0.0136(4) 1.6472(4) 0.73647(11) 0.0251(6) Uani 1 1 d . . . H24 H 0.0685 1.6527 0.7047 0.030 Uiso 1 1 calc R . . C25 C -0.1572(4) 1.7086(4) 0.74234(13) 0.0259(6) Uani 1 1 d . . . H25 H -0.2188 1.7543 0.7144 0.031 Uiso 1 1 calc R . . C26 C -0.2393(4) 1.7047(4) 0.78786(12) 0.0259(6) Uani 1 1 d . . . H26 H -0.3564 1.7485 0.7910 0.031 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 C1 0.0313(15) 0.0238(14) 0.0416(19) -0.0086(13) 0.0078(13) -0.0016(12) C2 0.0411(18) 0.0232(14) 0.0334(18) -0.0059(12) -0.0009(13) -0.0107(13) C3 0.0338(16) 0.0321(16) 0.0410(19) -0.0119(14) 0.0155(14) -0.0108(13) C4 0.0333(17) 0.0362(18) 0.055(2) -0.0148(16) 0.0024(16) -0.0125(14) C5 0.0305(16) 0.0356(17) 0.054(2) -0.0087(15) 0.0000(15) -0.0044(14) C6 0.049(2) 0.0378(17) 0.0284(17) -0.0048(13) -0.0011(14) -0.0014(15) O1 0.0311(12) 0.0495(15) 0.0527(17) 0.0023(12) 0.0053(11) 0.0039(11) O4 0.0060(8) 0.0569(15) 0.0582(17) -0.0245(13) 0.0042(9) 0.0042(9) Cl2 0.0430(5) 0.0381(4) 0.0362(4) 0.0045(3) -0.0064(3) -0.0029(3) C11 0.0287(14) 0.0241(13) 0.0235(14) -0.0053(11) 0.0065(11) -0.0037(10) C12 0.0244(13) 0.0233(13) 0.0294(16) -0.0024(11) -0.0044(11) -0.0018(10) C13 0.0167(12) 0.0218(13) 0.0338(16) -0.0038(11) 0.0008(11) -0.0020(9) C14 0.0153(11) 0.0151(11) 0.0315(15) -0.0040(10) 0.0023(10) -0.0046(9) C15 0.0158(11) 0.0131(11) 0.0315(15) -0.0046(10) 0.0046(10) -0.0023(8) C16 0.0173(12) 0.0157(12) 0.0345(16) -0.0067(10) 0.0059(10) -0.0021(9) C17 0.0149(12) 0.0216(13) 0.0405(18) -0.0067(11) 0.0073(11) 0.0004(9) C18 0.0229(13) 0.0239(13) 0.0324(15) -0.0068(12) 0.0129(11) -0.0046(10) C19 0.0181(12) 0.0186(11) 0.0288(16) -0.0048(10) 0.0049(10) -0.0035(9) C20 0.0149(12) 0.0181(12) 0.0250(14) -0.0061(10) 0.0037(9) -0.0032(9) C21 0.0126(11) 0.0199(12) 0.0349(16) -0.0046(10) 0.0059(10) -0.0016(9) C22 0.0209(13) 0.0186(12) 0.0309(16) -0.0023(10) 0.0103(11) -0.0004(10) C23 0.0146(12) 0.0161(11) 0.0317(15) -0.0030(10) 0.0030(10) -0.0007(9) C24 0.0263(14) 0.0193(12) 0.0297(16) 0.0025(10) 0.0046(12) 0.0009(10) C25 0.0228(13) 0.0205(13) 0.0345(17) 0.0021(11) -0.0030(12) 0.0025(10) C26 0.0166(12) 0.0192(12) 0.0421(17) -0.0035(11) 0.0001(11) -0.0016(10) _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 C1 O1 1.199(4) . ? C1 C6 1.472(5) . ? C1 C2 1.490(5) . ? C2 C3 1.312(5) . ? C2 Cl2 1.711(4) . ? C3 C4 1.469(6) . ? C4 O4 1.213(4) . ? C4 C5 1.500(6) . ? C5 C6 1.324(5) . ? C11 C12 1.388(4) . ? C11 C19 1.410(4) . ? C12 C13 1.389(4) . ? C13 C14 1.395(4) . ? C14 C20 1.426(3) . ? C14 C21 1.439(4) . ? C15 C23 1.417(4) . ? C15 C20 1.420(4) . ? C15 C16 1.427(3) . ? C16 C26 1.404(4) . ? C16 C17 1.430(4) . ? C17 C18 1.346(5) . ? C18 C19 1.437(4) . ? C19 C20 1.418(4) . ? C21 C22 1.349(4) . ? C22 C23 1.445(4) . ? C23 C24 1.402(4) . ? C24 C25 1.383(4) . ? C25 C26 1.373(5) . ? 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 O1 C1 C6 122.2(3) . . ? O1 C1 C2 122.0(3) . . ? C6 C1 C2 115.8(3) . . ? C3 C2 C1 122.8(3) . . ? C3 C2 Cl2 121.8(3) . . ? C1 C2 Cl2 115.4(3) . . ? C2 C3 C4 120.9(3) . . ? O4 C4 C3 118.9(4) . . ? O4 C4 C5 123.2(4) . . ? C3 C4 C5 117.7(3) . . ? C6 C5 C4 119.9(4) . . ? C5 C6 C1 122.9(4) . . ? C12 C11 C19 120.7(3) . . ? C11 C12 C13 120.5(3) . . ? C12 C13 C14 120.8(2) . . ? C13 C14 C20 119.3(2) . . ? C13 C14 C21 122.3(2) . . ? C20 C14 C21 118.4(3) . . ? C23 C15 C20 120.3(2) . . ? C23 C15 C16 119.8(3) . . ? C20 C15 C16 119.9(2) . . ? C26 C16 C15 118.6(3) . . ? C26 C16 C17 122.7(2) . . ? C15 C16 C17 118.7(3) . . ? C18 C17 C16 121.3(3) . . ? C17 C18 C19 121.5(3) . . ? C11 C19 C20 118.9(2) . . ? C11 C19 C18 122.6(3) . . ? C20 C19 C18 118.5(3) . . ? C19 C20 C15 120.1(2) . . ? C19 C20 C14 119.8(3) . . ? C15 C20 C14 120.1(2) . . ? C22 C21 C14 121.4(2) . . ? C21 C22 C23 121.4(3) . . ? C24 C23 C15 119.1(2) . . ? C24 C23 C22 122.5(3) . . ? C15 C23 C22 118.4(3) . . ? C25 C24 C23 120.4(3) . . ? C26 C25 C24 121.2(3) . . ? C25 C26 C16 120.8(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.600 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.084 #===END