# 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_8 _database_code_depnum_ccdc_archive 'CCDC 922362' #TrackingRef '8.cif' # start Validation Reply Form _vrf_PLAT029_8 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.924 RESPONSE: no diffraction at higher angles. Other crystals tried but gave poorer structures and Flack. ; # end Validation Reply Form _chemical_formula_sum 'C22 H22 O4' _chemical_formula_moiety 'C22 H22 O4' _chemical_formula_weight 350.41 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 12.174(6) _cell_length_b 6.293(3) _cell_length_c 12.398(6) _cell_angle_alpha 90.0000 _cell_angle_beta 98.901(14) _cell_angle_gamma 90.0000 _cell_volume 938.3(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1092 _cell_measurement_theta_min 21.35 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372.00 _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.688 _exptl_absorpt_correction_T_max 0.966 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 29.257 _diffrn_reflns_number 9926 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_theta_max 68.52 _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.933 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3143 _reflns_number_gt 2932 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1347 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3143 _refine_ls_number_parameters 235 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.1844P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.290 _refine_diff_density_min -0.190 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1387 Friedel Pairs' _refine_ls_abs_structure_Flack 0.1(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O1 O 0.32324(15) 0.5316(3) 0.16708(15) 0.0472(5) Uani 1.0 2 d . . . O22 O 0.35339(15) 0.2972(4) -0.08419(16) 0.0589(6) Uani 1.0 2 d . . . O2 O 0.32150(16) 0.6344(3) 0.33483(16) 0.0541(5) Uani 1.0 2 d . . . O21 O 0.40877(19) 0.6150(4) -0.01303(19) 0.0730(7) Uani 1.0 2 d . . . C2 C 0.3083(2) 0.4877(4) 0.2723(2) 0.0412(6) Uani 1.0 2 d . . . C3 C 0.28746(18) 0.2583(4) 0.3013(2) 0.0354(6) Uani 1.0 2 d . . . C4 C 0.21858(18) 0.1408(4) 0.20222(19) 0.0381(6) Uani 1.0 2 d . . . C5 C 0.2680(2) 0.1863(4) 0.1010(3) 0.0438(6) Uani 1.0 2 d . . . C6 C 0.3149(2) 0.3735(5) 0.0886(2) 0.0438(6) Uani 1.0 2 d . . . C7 C 0.40720(18) 0.1591(4) 0.3225(2) 0.0395(6) Uani 1.0 2 d . . . C8 C 0.4840(3) 0.2482(4) 0.4205(3) 0.0505(7) Uani 1.0 2 d . . . C9 C 0.22964(19) 0.2372(4) 0.4018(2) 0.0382(6) Uani 1.0 2 d . . . C10 C 0.2340(2) 0.0413(4) 0.4557(2) 0.0425(6) Uani 1.0 2 d . . . C11 C 0.1782(3) 0.0081(4) 0.5436(3) 0.0478(6) Uani 1.0 2 d . . . C12 C 0.1178(2) 0.1702(5) 0.5809(3) 0.0497(7) Uani 1.0 2 d . . . C13 C 0.1114(2) 0.3634(5) 0.5285(3) 0.0522(7) Uani 1.0 2 d . . . C14 C 0.1660(2) 0.3975(5) 0.4396(3) 0.0459(6) Uani 1.0 2 d . . . C15 C 0.09436(19) 0.1938(4) 0.1835(2) 0.0399(6) Uani 1.0 2 d . . . C16 C 0.0547(3) 0.3870(5) 0.1395(3) 0.0534(7) Uani 1.0 2 d . . . C17 C -0.0589(3) 0.4324(6) 0.1233(3) 0.0630(9) Uani 1.0 2 d . . . C18 C -0.1327(3) 0.2837(7) 0.1500(3) 0.0657(9) Uani 1.0 2 d . . . C19 C -0.0948(3) 0.0897(6) 0.1915(3) 0.0697(10) Uani 1.0 2 d . . . C20 C 0.0186(3) 0.0458(5) 0.2090(3) 0.0543(7) Uani 1.0 2 d . . . C21 C 0.3649(3) 0.4451(5) -0.0062(3) 0.0529(7) Uani 1.0 2 d . . . C23 C 0.4116(3) 0.3378(7) -0.1756(3) 0.0735(11) Uani 1.0 2 d . . . C24 C 0.4003(3) 0.1512(10) -0.2435(4) 0.1007(15) Uani 1.0 2 d . . . H4 H 0.2260 -0.0153 0.2167 0.0458 Uiso 1.0 2 calc R . . H5 H 0.2658 0.0810 0.0457 0.0525 Uiso 1.0 2 calc R . . H7A H 0.4001 0.0040 0.3326 0.0474 Uiso 1.0 2 calc R . . H7B H 0.4425 0.1811 0.2566 0.0474 Uiso 1.0 2 calc R . . H8A H 0.4958 0.4002 0.4094 0.0606 Uiso 1.0 2 calc R . . H8B H 0.5555 0.1737 0.4287 0.0606 Uiso 1.0 2 calc R . . H8C H 0.4501 0.2280 0.4865 0.0606 Uiso 1.0 2 calc R . . H10 H 0.2761 -0.0714 0.4315 0.0510 Uiso 1.0 2 calc R . . H11 H 0.1816 -0.1268 0.5784 0.0573 Uiso 1.0 2 calc R . . H12 H 0.0809 0.1487 0.6422 0.0596 Uiso 1.0 2 calc R . . H13 H 0.0690 0.4749 0.5534 0.0626 Uiso 1.0 2 calc R . . H14 H 0.1600 0.5317 0.4041 0.0551 Uiso 1.0 2 calc R . . H16 H 0.1055 0.4896 0.1202 0.0640 Uiso 1.0 2 calc R . . H17 H -0.0850 0.5658 0.0939 0.0756 Uiso 1.0 2 calc R . . H18 H -0.2100 0.3148 0.1399 0.0788 Uiso 1.0 2 calc R . . H19 H -0.1462 -0.0144 0.2083 0.0837 Uiso 1.0 2 calc R . . H20 H 0.0442 -0.0875 0.2389 0.0651 Uiso 1.0 2 calc R . . H23A H 0.3789 0.4625 -0.2176 0.0883 Uiso 1.0 2 calc R . . H23B H 0.4910 0.3673 -0.1492 0.0883 Uiso 1.0 2 calc R . . H24A H 0.4364 0.0305 -0.2023 0.1208 Uiso 1.0 2 calc R . . H24B H 0.4357 0.1763 -0.3082 0.1208 Uiso 1.0 2 calc R . . H24C H 0.3213 0.1197 -0.2662 0.1208 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0595(11) 0.0355(9) 0.0463(12) -0.0058(8) 0.0074(8) 0.0034(8) O22 0.0481(10) 0.0884(15) 0.0414(13) -0.0079(10) 0.0108(8) 0.0037(11) O2 0.0738(12) 0.0289(9) 0.0614(13) -0.0034(9) 0.0160(9) -0.0098(8) O21 0.0781(14) 0.0808(16) 0.0599(15) -0.0280(13) 0.0098(11) 0.0179(12) C2 0.0472(13) 0.0309(12) 0.0453(17) 0.0023(10) 0.0068(11) 0.0019(10) C3 0.0407(12) 0.0263(11) 0.0391(15) -0.0008(9) 0.0056(10) -0.0028(9) C4 0.0418(11) 0.0330(11) 0.0397(15) -0.0025(10) 0.0063(10) -0.0034(10) C5 0.0433(12) 0.0454(15) 0.0423(16) -0.0041(11) 0.0056(10) -0.0067(11) C6 0.0459(13) 0.0475(13) 0.0366(15) -0.0028(11) 0.0018(10) 0.0026(12) C7 0.0415(12) 0.0288(11) 0.0478(16) 0.0019(10) 0.0050(10) 0.0018(10) C8 0.0535(15) 0.0414(14) 0.0529(18) -0.0016(12) -0.0030(12) 0.0044(12) C9 0.0390(12) 0.0349(12) 0.0396(15) -0.0005(9) 0.0031(10) -0.0051(10) C10 0.0507(14) 0.0314(11) 0.0466(16) 0.0016(10) 0.0113(11) -0.0035(10) C11 0.0558(15) 0.0421(14) 0.0464(17) -0.0054(12) 0.0111(12) 0.0013(12) C12 0.0466(13) 0.0619(17) 0.0422(16) -0.0029(12) 0.0120(11) -0.0036(13) C13 0.0455(14) 0.0576(16) 0.0549(18) 0.0121(13) 0.0124(12) -0.0056(13) C14 0.0477(13) 0.0406(13) 0.0490(17) 0.0084(11) 0.0064(11) -0.0003(12) C15 0.0415(12) 0.0435(14) 0.0339(15) -0.0049(10) 0.0032(10) -0.0044(10) C16 0.0459(13) 0.0503(15) 0.0608(19) -0.0067(12) -0.0018(12) 0.0057(13) C17 0.0495(15) 0.0653(19) 0.068(3) 0.0055(14) -0.0090(14) 0.0087(15) C18 0.0436(15) 0.091(3) 0.060(2) -0.0007(16) 0.0007(13) 0.0044(18) C19 0.0425(14) 0.093(3) 0.073(3) -0.0121(16) 0.0083(13) 0.0177(19) C20 0.0459(14) 0.0572(16) 0.0590(19) -0.0089(12) 0.0063(12) 0.0111(14) C21 0.0472(14) 0.0692(19) 0.0406(18) -0.0091(13) 0.0016(11) 0.0064(13) C23 0.0551(17) 0.124(4) 0.044(2) 0.0023(19) 0.0169(14) 0.013(2) C24 0.065(2) 0.178(5) 0.063(3) -0.007(3) 0.0221(17) -0.028(3) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r2' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r2' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C2 1.373(4) yes . . O1 C6 1.384(4) yes . . O22 C21 1.334(4) yes . . O22 C23 1.449(5) yes . . O2 C2 1.200(3) yes . . O21 C21 1.204(4) yes . . C2 C3 1.518(4) yes . . C3 C4 1.563(4) yes . . C3 C7 1.570(4) yes . . C3 C9 1.529(4) yes . . C4 C5 1.501(4) yes . . C4 C15 1.531(4) yes . . C5 C6 1.328(4) yes . . C6 C21 1.475(5) yes . . C7 C8 1.521(4) yes . . C9 C10 1.399(4) yes . . C9 C14 1.396(4) yes . . C10 C11 1.387(4) yes . . C11 C12 1.378(4) yes . . C12 C13 1.375(5) yes . . C13 C14 1.390(5) yes . . C15 C16 1.388(4) yes . . C15 C20 1.382(4) yes . . C16 C17 1.395(4) yes . . C17 C18 1.373(5) yes . . C18 C19 1.377(6) yes . . C19 C20 1.391(4) yes . . C23 C24 1.439(7) yes . . C4 H4 1.000 no . . C5 H5 0.950 no . . C7 H7A 0.990 no . . C7 H7B 0.990 no . . C8 H8A 0.980 no . . C8 H8B 0.980 no . . C8 H8C 0.980 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C20 H20 0.950 no . . C23 H23A 0.990 no . . C23 H23B 0.990 no . . C24 H24A 0.980 no . . C24 H24B 0.980 no . . C24 H24C 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 O1 C6 121.13(19) yes . . . C21 O22 C23 115.8(3) yes . . . O1 C2 O2 115.8(2) yes . . . O1 C2 C3 117.9(2) yes . . . O2 C2 C3 126.1(3) yes . . . C2 C3 C4 110.63(19) yes . . . C2 C3 C7 103.46(18) yes . . . C2 C3 C9 113.0(2) yes . . . C4 C3 C7 108.33(19) yes . . . C4 C3 C9 109.94(19) yes . . . C7 C3 C9 111.23(19) yes . . . C3 C4 C5 109.4(2) yes . . . C3 C4 C15 114.4(2) yes . . . C5 C4 C15 110.24(19) yes . . . C4 C5 C6 120.0(3) yes . . . O1 C6 C5 122.9(3) yes . . . O1 C6 C21 110.2(3) yes . . . C5 C6 C21 126.9(3) yes . . . C3 C7 C8 115.3(2) yes . . . C3 C9 C10 118.5(2) yes . . . C3 C9 C14 124.0(3) yes . . . C10 C9 C14 117.3(3) yes . . . C9 C10 C11 121.4(3) yes . . . C10 C11 C12 120.3(3) yes . . . C11 C12 C13 119.4(3) yes . . . C12 C13 C14 120.8(3) yes . . . C9 C14 C13 120.9(3) yes . . . C4 C15 C16 121.7(3) yes . . . C4 C15 C20 119.8(3) yes . . . C16 C15 C20 118.4(3) yes . . . C15 C16 C17 120.8(3) yes . . . C16 C17 C18 119.8(3) yes . . . C17 C18 C19 120.0(3) yes . . . C18 C19 C20 120.1(3) yes . . . C15 C20 C19 120.8(3) yes . . . O22 C21 O21 124.5(3) yes . . . O22 C21 C6 110.8(3) yes . . . O21 C21 C6 124.7(3) yes . . . O22 C23 C24 107.5(4) yes . . . C3 C4 H4 107.503 no . . . C5 C4 H4 107.512 no . . . C15 C4 H4 107.502 no . . . C4 C5 H5 119.987 no . . . C6 C5 H5 119.976 no . . . C3 C7 H7A 108.457 no . . . C3 C7 H7B 108.456 no . . . C8 C7 H7A 108.459 no . . . C8 C7 H7B 108.455 no . . . H7A C7 H7B 107.488 no . . . C7 C8 H8A 109.472 no . . . C7 C8 H8B 109.471 no . . . C7 C8 H8C 109.466 no . . . H8A C8 H8B 109.477 no . . . H8A C8 H8C 109.463 no . . . H8B C8 H8C 109.477 no . . . C9 C10 H10 119.325 no . . . C11 C10 H10 119.318 no . . . C10 C11 H11 119.874 no . . . C12 C11 H11 119.866 no . . . C11 C12 H12 120.316 no . . . C13 C12 H12 120.309 no . . . C12 C13 H13 119.611 no . . . C14 C13 H13 119.606 no . . . C9 C14 H14 119.556 no . . . C13 C14 H14 119.558 no . . . C15 C16 H16 119.590 no . . . C17 C16 H16 119.593 no . . . C16 C17 H17 120.092 no . . . C18 C17 H17 120.105 no . . . C17 C18 H18 119.996 no . . . C19 C18 H18 119.990 no . . . C18 C19 H19 119.954 no . . . C20 C19 H19 119.956 no . . . C15 C20 H20 119.593 no . . . C19 C20 H20 119.591 no . . . O22 C23 H23A 110.216 no . . . O22 C23 H23B 110.217 no . . . C24 C23 H23A 110.220 no . . . C24 C23 H23B 110.221 no . . . H23A C23 H23B 108.499 no . . . C23 C24 H24A 109.475 no . . . C23 C24 H24B 109.470 no . . . C23 C24 H24C 109.476 no . . . H24A C24 H24B 109.463 no . . . H24A C24 H24C 109.472 no . . . H24B C24 H24C 109.471 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 O1 C6 C5 15.9(4) no . . . . C2 O1 C6 C21 -163.80(18) no . . . . C6 O1 C2 O2 177.29(19) no . . . . C6 O1 C2 C3 2.7(3) no . . . . C21 O22 C23 C24 173.1(2) no . . . . C23 O22 C21 O21 8.6(4) no . . . . C23 O22 C21 C6 -172.5(2) no . . . . O1 C2 C3 C4 -34.3(3) no . . . . O1 C2 C3 C7 81.5(3) no . . . . O1 C2 C3 C9 -158.07(18) no . . . . O2 C2 C3 C4 151.8(3) no . . . . O2 C2 C3 C7 -92.4(3) no . . . . O2 C2 C3 C9 28.0(4) no . . . . C2 C3 C4 C5 47.2(3) no . . . . C2 C3 C4 C15 -77.0(3) no . . . . C2 C3 C7 C8 65.5(3) no . . . . C2 C3 C9 C10 -161.90(17) no . . . . C2 C3 C9 C14 22.5(3) no . . . . C4 C3 C7 C8 -177.05(17) no . . . . C7 C3 C4 C5 -65.5(3) no . . . . C7 C3 C4 C15 170.24(17) no . . . . C4 C3 C9 C10 73.9(3) no . . . . C4 C3 C9 C14 -101.6(3) no . . . . C9 C3 C4 C5 172.74(16) no . . . . C9 C3 C4 C15 48.5(3) no . . . . C7 C3 C9 C10 -46.0(3) no . . . . C7 C3 C9 C14 138.40(19) no . . . . C9 C3 C7 C8 -56.1(3) no . . . . C3 C4 C5 C6 -33.3(3) no . . . . C3 C4 C15 C16 74.1(3) no . . . . C3 C4 C15 C20 -106.8(3) no . . . . C5 C4 C15 C16 -49.6(3) no . . . . C5 C4 C15 C20 129.4(2) no . . . . C15 C4 C5 C6 93.4(3) no . . . . C4 C5 C6 O1 1.6(4) no . . . . C4 C5 C6 C21 -178.68(19) no . . . . O1 C6 C21 O22 -177.52(18) no . . . . O1 C6 C21 O21 1.4(4) no . . . . C5 C6 C21 O22 2.8(4) no . . . . C5 C6 C21 O21 -178.3(3) no . . . . C3 C9 C10 C11 -176.41(18) no . . . . C3 C9 C14 C13 176.83(18) no . . . . C10 C9 C14 C13 1.2(4) no . . . . C14 C9 C10 C11 -0.5(4) no . . . . C9 C10 C11 C12 -0.8(4) no . . . . C10 C11 C12 C13 1.4(4) no . . . . C11 C12 C13 C14 -0.8(4) no . . . . C12 C13 C14 C9 -0.6(4) no . . . . C4 C15 C16 C17 -179.8(2) no . . . . C4 C15 C20 C19 -179.3(2) no . . . . C16 C15 C20 C19 -0.2(4) no . . . . C20 C15 C16 C17 1.1(4) no . . . . C15 C16 C17 C18 -0.7(5) no . . . . C16 C17 C18 C19 -0.7(5) no . . . . C17 C18 C19 C20 1.6(5) no . . . . C18 C19 C20 C15 -1.1(5) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 O22 3.517(3) no . . O1 O21 2.658(4) no . . O1 C4 2.834(3) no . . O1 C7 3.105(3) no . . O1 C15 3.536(4) no . . O1 C16 3.359(4) no . . O22 C5 2.753(4) no . . O2 C6 3.456(4) no . . O2 C7 3.179(3) no . . O2 C8 3.209(4) no . . O2 C9 2.911(3) no . . O2 C14 2.873(4) no . . O21 C23 2.670(5) no . . C2 C5 2.833(4) no . . C2 C8 3.001(4) no . . C2 C14 2.956(4) no . . C2 C15 3.245(4) no . . C2 C16 3.327(4) no . . C3 C6 2.805(4) no . . C3 C16 3.309(4) no . . C3 C20 3.558(4) no . . C4 C10 3.181(4) no . . C4 C14 3.502(4) no . . C5 C7 3.000(4) no . . C5 C16 2.992(4) no . . C6 C7 3.238(4) no . . C6 C15 3.293(4) no . . C6 C16 3.325(4) no . . C7 C10 2.966(4) no . . C8 C9 3.070(4) no . . C8 C10 3.399(4) no . . C9 C12 2.810(4) no . . C9 C15 2.956(4) no . . C9 C20 3.445(4) no . . C10 C13 2.752(4) no . . C11 C14 2.762(4) no . . C14 C15 3.411(4) no . . C15 C18 2.789(4) no . . C16 C19 2.756(5) no . . C17 C20 2.761(5) no . . C21 C24 3.558(6) no . . O1 C24 3.435(5) no . 2_655 O22 O21 3.174(4) no . 2_645 O2 C7 3.473(4) no . 1_565 O2 C10 3.229(4) no . 1_565 O21 O22 3.174(4) no . 2_655 O21 C21 3.429(4) no . 2_655 O21 C23 3.262(4) no . 2_655 C7 O2 3.473(4) no . 1_545 C10 O2 3.229(4) no . 1_545 C11 C24 3.589(5) no . 1_556 C12 C13 3.490(4) no . 2_546 C13 C12 3.490(4) no . 2_556 C21 O21 3.429(4) no . 2_645 C23 O21 3.262(4) no . 2_645 C24 O1 3.435(5) no . 2_645 C24 C11 3.589(5) no . 1_554 O1 H5 3.2351 no . . O1 H7B 2.7754 no . . O1 H8A 3.4887 no . . O1 H16 2.6374 no . . O22 H5 2.4726 no . . O22 H24A 2.5379 no . . O22 H24B 3.1871 no . . O22 H24C 2.4943 no . . O2 H7B 3.4188 no . . O2 H8A 2.6313 no . . O2 H8C 3.4080 no . . O2 H14 2.3537 no . . O2 H16 3.5580 no . . O21 H23A 2.6828 no . . O21 H23B 2.6092 no . . C2 H4 3.3586 no . . C2 H7A 3.2888 no . . C2 H7B 2.5546 no . . C2 H8A 2.6841 no . . C2 H8C 3.3589 no . . C2 H14 2.6295 no . . C2 H16 2.8650 no . . C3 H5 3.3313 no . . C3 H8A 2.8237 no . . C3 H8B 3.4393 no . . C3 H8C 2.7959 no . . C3 H10 2.6450 no . . C3 H14 2.7563 no . . C3 H16 3.2447 no . . C4 H7A 2.6710 no . . C4 H7B 2.7164 no . . C4 H10 3.1202 no . . C4 H16 2.7043 no . . C4 H20 2.6604 no . . C5 H7A 3.2743 no . . C5 H7B 2.6389 no . . C5 H16 2.7857 no . . C6 H4 3.1956 no . . C6 H7B 2.6859 no . . C6 H16 2.7369 no . . C7 H4 2.6256 no . . C7 H10 2.6729 no . . C8 H10 3.2515 no . . C9 H4 2.7857 no . . C9 H7A 2.7836 no . . C9 H7B 3.3949 no . . C9 H8A 3.3861 no . . C9 H8C 2.7265 no . . C9 H11 3.2824 no . . C9 H13 3.2757 no . . C9 H20 3.4559 no . . C10 H4 2.9700 no . . C10 H7A 2.7247 no . . C10 H8C 2.8517 no . . C10 H12 3.2575 no . . C10 H14 3.2503 no . . C10 H20 3.3616 no . . C11 H13 3.2342 no . . C12 H10 3.2500 no . . C12 H14 3.2547 no . . C13 H11 3.2351 no . . C14 H8C 3.5791 no . . C14 H10 3.2484 no . . C14 H12 3.2615 no . . C15 H5 2.9796 no . . C15 H14 3.4589 no . . C15 H17 3.2755 no . . C15 H19 3.2652 no . . C16 H4 3.3249 no . . C16 H5 3.5480 no . . C16 H14 3.4538 no . . C16 H18 3.2553 no . . C16 H20 3.2403 no . . C17 H19 3.2389 no . . C18 H16 3.2495 no . . C18 H20 3.2517 no . . C19 H17 3.2403 no . . C20 H4 2.5416 no . . C20 H16 3.2393 no . . C20 H18 3.2563 no . . C21 H5 2.7126 no . . C21 H23A 2.6549 no . . C21 H23B 2.5664 no . . H4 H5 2.3269 no . . H4 H7A 2.3727 no . . H4 H7B 2.8833 no . . H4 H10 2.6612 no . . H4 H20 2.3174 no . . H5 H7B 3.1801 no . . H5 H16 3.4393 no . . H7A H8A 2.8523 no . . H7A H8B 2.3324 no . . H7A H8C 2.3740 no . . H7A H10 2.1396 no . . H7B H8A 2.3519 no . . H7B H8B 2.3539 no . . H7B H8C 2.8529 no . . H7B H10 3.5622 no . . H8C H10 2.8377 no . . H10 H11 2.3257 no . . H10 H20 3.4055 no . . H11 H12 2.3311 no . . H12 H13 2.3235 no . . H13 H14 2.3278 no . . H14 H16 3.4889 no . . H16 H17 2.3409 no . . H17 H18 2.3249 no . . H18 H19 2.3260 no . . H19 H20 2.3347 no . . H23A H24A 2.8059 no . . H23A H24B 2.2858 no . . H23A H24C 2.3193 no . . H23B H24A 2.2872 no . . H23B H24B 2.3177 no . . H23B H24C 2.8060 no . . O1 H4 3.1836 no . 1_565 O1 H23B 3.1266 no . 2_655 O1 H24A 2.8912 no . 2_655 O1 H24B 3.3035 no . 2_655 O22 H17 3.5624 no . 2_545 O22 H18 3.5166 no . 2_545 O22 H19 2.9892 no . 2_555 O2 H4 2.7978 no . 1_565 O2 H7A 2.5163 no . 1_565 O2 H8B 3.0889 no . 2_656 O2 H8C 3.3289 no . 2_656 O2 H10 2.3180 no . 1_565 O2 H24B 3.0361 no . 2_655 O21 H5 3.5429 no . 1_565 O21 H18 2.9547 no . 2_555 O21 H23B 2.7011 no . 2_655 O21 H24A 3.5641 no . 1_565 O21 H24A 3.0672 no . 2_655 C2 H4 3.3237 no . 1_565 C2 H7A 3.4792 no . 1_565 C2 H10 3.4621 no . 1_565 C2 H24A 3.3649 no . 2_655 C2 H24B 3.3003 no . 2_655 C5 H17 3.1168 no . 2_545 C5 H23B 3.5280 no . 2_645 C6 H24A 3.2884 no . 2_655 C7 H23A 3.3242 no . 2_645 C7 H23B 3.2162 no . 2_645 C7 H24A 3.4907 no . 2_655 C8 H7A 3.5517 no . 2_656 C8 H8A 3.0239 no . 2_646 C8 H8B 3.3433 no . 2_656 C8 H8C 3.5218 no . 2_646 C8 H8C 3.2873 no . 2_656 C8 H10 3.3957 no . 2_656 C8 H24A 3.4961 no . 2_655 C8 H24B 3.5325 no . 1_556 C8 H24B 3.2515 no . 2_655 C10 H8A 3.5639 no . 2_646 C10 H8B 3.5824 no . 2_646 C10 H14 3.3654 no . 1_545 C10 H24C 3.4825 no . 1_556 C11 H13 3.0706 no . 2_546 C11 H14 3.4519 no . 1_545 C11 H24B 3.5407 no . 1_556 C11 H24C 2.7952 no . 1_556 C12 H13 2.8779 no . 2_546 C12 H14 3.5256 no . 2_546 C12 H19 3.2574 no . 2_556 C12 H20 3.5450 no . 2_556 C12 H24C 2.8946 no . 1_556 C13 H11 3.3527 no . 1_565 C13 H12 3.4129 no . 2_556 C13 H13 3.3374 no . 2_546 C13 H19 3.3154 no . 2_556 C14 H11 3.4432 no . 1_565 C14 H12 3.4092 no . 2_556 C15 H17 3.5167 no . 2_545 C16 H17 3.5955 no . 2_545 C16 H20 3.5380 no . 1_565 C17 H5 3.1596 no . 2_555 C17 H12 3.2585 no . 2_556 C17 H20 3.4921 no . 1_565 C18 H5 3.2863 no . 2_555 C18 H11 3.5541 no . 2_556 C18 H12 3.4359 no . 2_556 C18 H24C 3.5829 no . 2_555 C19 H12 3.4456 no . 2_546 C19 H13 3.2113 no . 2_546 C19 H17 3.5201 no . 1_545 C20 H12 3.4362 no . 2_546 C20 H13 3.3142 no . 2_546 C20 H17 3.4915 no . 1_545 C21 H18 3.2785 no . 2_555 C21 H19 3.3723 no . 2_555 C21 H23B 3.5774 no . 2_655 C21 H24A 3.2994 no . 2_655 C23 H7A 3.3942 no . 2_655 C23 H7B 3.0636 no . 2_655 C23 H19 3.3261 no . 2_555 C24 H7A 3.5890 no . 2_655 C24 H7B 3.5402 no . 2_645 C24 H8A 3.0216 no . 2_645 C24 H8C 3.5264 no . 1_554 C24 H18 3.5243 no . 2_545 H4 O1 3.1836 no . 1_545 H4 O2 2.7978 no . 1_545 H4 C2 3.3237 no . 1_545 H4 H16 3.5704 no . 1_545 H5 O21 3.5429 no . 1_545 H5 C17 3.1596 no . 2_545 H5 C18 3.2863 no . 2_545 H5 H17 2.5838 no . 2_545 H5 H18 2.8426 no . 2_545 H5 H23B 3.3227 no . 2_645 H7A O2 2.5163 no . 1_545 H7A C2 3.4792 no . 1_545 H7A C8 3.5517 no . 2_646 H7A C23 3.3942 no . 2_645 H7A C24 3.5890 no . 2_645 H7A H8A 3.3175 no . 2_646 H7A H8B 3.5876 no . 2_646 H7A H8C 3.1789 no . 2_646 H7A H23A 3.2445 no . 2_645 H7A H23B 2.9322 no . 2_645 H7A H24B 2.9200 no . 2_645 H7B C23 3.0636 no . 2_645 H7B C24 3.5402 no . 2_655 H7B H23A 2.6795 no . 2_645 H7B H23B 2.5806 no . 2_645 H7B H24A 2.7870 no . 2_655 H7B H24B 3.5226 no . 2_645 H7B H24B 3.4675 no . 2_655 H8A C8 3.0239 no . 2_656 H8A C10 3.5639 no . 2_656 H8A C24 3.0216 no . 2_655 H8A H7A 3.3175 no . 2_656 H8A H8B 2.7876 no . 2_656 H8A H8C 2.4685 no . 2_656 H8A H10 3.1526 no . 2_656 H8A H24A 2.9329 no . 2_655 H8A H24B 2.3691 no . 2_655 H8A H24C 3.3526 no . 2_655 H8B O2 3.0889 no . 2_646 H8B C8 3.3433 no . 2_646 H8B C10 3.5824 no . 2_656 H8B H7A 3.5876 no . 2_656 H8B H8A 2.7876 no . 2_646 H8B H8C 3.0000 no . 2_646 H8B H10 2.9464 no . 2_656 H8B H11 3.4511 no . 2_656 H8B H23A 3.1469 no . 2_645 H8B H24B 3.4773 no . 2_645 H8B H24B 3.5061 no . 2_655 H8C O2 3.3289 no . 2_646 H8C C8 3.2873 no . 2_646 H8C C8 3.5218 no . 2_656 H8C C24 3.5264 no . 1_556 H8C H7A 3.1789 no . 2_656 H8C H8A 2.4685 no . 2_646 H8C H8B 3.0000 no . 2_656 H8C H8C 3.3710 no . 2_646 H8C H8C 3.3710 no . 2_656 H8C H10 3.5625 no . 2_656 H8C H24B 2.5991 no . 1_556 H10 O2 2.3180 no . 1_545 H10 C2 3.4621 no . 1_545 H10 C8 3.3957 no . 2_646 H10 H8A 3.1526 no . 2_646 H10 H8B 2.9464 no . 2_646 H10 H8C 3.5625 no . 2_646 H10 H14 2.8640 no . 1_545 H11 C13 3.3527 no . 1_545 H11 C14 3.4432 no . 1_545 H11 C18 3.5541 no . 2_546 H11 H8B 3.4511 no . 2_646 H11 H13 2.8503 no . 1_545 H11 H13 3.2935 no . 2_546 H11 H14 3.0302 no . 1_545 H11 H18 3.4765 no . 2_546 H11 H24C 2.8276 no . 1_556 H12 C13 3.4129 no . 2_546 H12 C14 3.4092 no . 2_546 H12 C17 3.2585 no . 2_546 H12 C18 3.4359 no . 2_546 H12 C19 3.4456 no . 2_556 H12 C20 3.4362 no . 2_556 H12 H13 3.0062 no . 2_546 H12 H14 2.9927 no . 2_546 H12 H17 3.3058 no . 2_546 H12 H18 3.5878 no . 2_546 H12 H19 2.8474 no . 2_556 H12 H20 2.8187 no . 2_556 H12 H24C 2.9760 no . 1_556 H13 C11 3.0706 no . 2_556 H13 C12 2.8779 no . 2_556 H13 C13 3.3374 no . 2_556 H13 C19 3.2113 no . 2_556 H13 C20 3.3142 no . 2_556 H13 H11 2.8503 no . 1_565 H13 H11 3.2935 no . 2_556 H13 H12 3.0062 no . 2_556 H13 H19 2.9595 no . 2_556 H13 H20 3.1278 no . 2_556 H14 C10 3.3654 no . 1_565 H14 C11 3.4519 no . 1_565 H14 C12 3.5256 no . 2_556 H14 H10 2.8640 no . 1_565 H14 H11 3.0302 no . 1_565 H14 H12 2.9927 no . 2_556 H14 H20 3.3215 no . 1_565 H16 H4 3.5704 no . 1_565 H16 H20 3.1850 no . 1_565 H17 O22 3.5624 no . 2_555 H17 C5 3.1168 no . 2_555 H17 C15 3.5167 no . 2_555 H17 C16 3.5955 no . 2_555 H17 C19 3.5201 no . 1_565 H17 C20 3.4915 no . 1_565 H17 H5 2.5838 no . 2_555 H17 H12 3.3058 no . 2_556 H17 H19 3.1415 no . 1_565 H17 H20 3.0960 no . 1_565 H18 O22 3.5166 no . 2_555 H18 O21 2.9547 no . 2_545 H18 C21 3.2785 no . 2_545 H18 C24 3.5243 no . 2_555 H18 H5 2.8426 no . 2_555 H18 H11 3.4765 no . 2_556 H18 H12 3.5878 no . 2_556 H18 H23A 3.2684 no . 2_545 H18 H24A 3.2705 no . 2_555 H18 H24C 2.9372 no . 2_555 H19 O22 2.9892 no . 2_545 H19 C12 3.2574 no . 2_546 H19 C13 3.3154 no . 2_546 H19 C21 3.3723 no . 2_545 H19 C23 3.3261 no . 2_545 H19 H12 2.8474 no . 2_546 H19 H13 2.9595 no . 2_546 H19 H17 3.1415 no . 1_545 H19 H23A 2.8575 no . 2_545 H19 H24C 3.2923 no . 2_545 H20 C12 3.5450 no . 2_546 H20 C16 3.5380 no . 1_545 H20 C17 3.4921 no . 1_545 H20 H12 2.8187 no . 2_546 H20 H13 3.1278 no . 2_546 H20 H14 3.3215 no . 1_545 H20 H16 3.1850 no . 1_545 H20 H17 3.0960 no . 1_545 H23A C7 3.3242 no . 2_655 H23A H7A 3.2445 no . 2_655 H23A H7B 2.6795 no . 2_655 H23A H8B 3.1469 no . 2_655 H23A H18 3.2684 no . 2_555 H23A H19 2.8575 no . 2_555 H23B O1 3.1266 no . 2_645 H23B O21 2.7011 no . 2_645 H23B C5 3.5280 no . 2_655 H23B C7 3.2162 no . 2_655 H23B C21 3.5774 no . 2_645 H23B H5 3.3227 no . 2_655 H23B H7A 2.9322 no . 2_655 H23B H7B 2.5806 no . 2_655 H24A O1 2.8912 no . 2_645 H24A O21 3.5641 no . 1_545 H24A O21 3.0672 no . 2_645 H24A C2 3.3649 no . 2_645 H24A C6 3.2884 no . 2_645 H24A C7 3.4907 no . 2_645 H24A C8 3.4961 no . 2_645 H24A C21 3.2994 no . 2_645 H24A H7B 2.7870 no . 2_645 H24A H8A 2.9329 no . 2_645 H24A H18 3.2705 no . 2_545 H24B O1 3.3035 no . 2_645 H24B O2 3.0361 no . 2_645 H24B C2 3.3003 no . 2_645 H24B C8 3.5325 no . 1_554 H24B C8 3.2515 no . 2_645 H24B C11 3.5407 no . 1_554 H24B H7A 2.9200 no . 2_655 H24B H7B 3.4675 no . 2_645 H24B H7B 3.5226 no . 2_655 H24B H8A 2.3691 no . 2_645 H24B H8B 3.5061 no . 2_645 H24B H8B 3.4773 no . 2_655 H24B H8C 2.5991 no . 1_554 H24C C10 3.4825 no . 1_554 H24C C11 2.7952 no . 1_554 H24C C12 2.8946 no . 1_554 H24C C18 3.5829 no . 2_545 H24C H8A 3.3526 no . 2_645 H24C H11 2.8276 no . 1_554 H24C H12 2.9760 no . 1_554 H24C H18 2.9372 no . 2_545 H24C H19 3.2923 no . 2_555 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================