# Electronic Supplementary Material (ESI) for CrystEngComm # 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_130704_150k #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C4 H6 Cu O6' _chemical_formula_moiety 'C4 H6 Cu O6' _chemical_formula_weight 213.63 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 5.178(4) _cell_length_b 7.208(5) _cell_length_c 8.889(7) _cell_angle_alpha 90.0000 _cell_angle_beta 100.840(9) _cell_angle_gamma 90.0000 _cell_volume 325.8(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 710 _cell_measurement_theta_min 3.70 _cell_measurement_theta_max 27.40 _cell_measurement_temperature 150 #------------------------------------------------------------------------------ _exptl_crystal_description unknown _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 2.177 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 214.00 _exptl_absorpt_coefficient_mu 3.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.520 _exptl_absorpt_correction_T_max 0.717 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 150 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.706 _diffrn_reflns_number 2356 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measured_fraction_theta_full 0.979 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _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 732 _reflns_number_gt 530 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1166 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refxyz _refine_ls_number_reflns 732 _refine_ls_number_parameters 64 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.0000P] 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 0.000 _refine_diff_density_max 0.930 _refine_diff_density_min -0.930 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 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) ; Cu Cu 0.3201 1.2651 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; 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 Cu1 Cu 0.0000 0.0000 0.0000 0.0161(4) Uani 1.0 2 d . . . O2 O 0.2316(8) -0.2071(6) -0.0277(4) 0.0191(9) Uani 1.0 4 d . . . O3 O -0.0643(7) -0.1474(5) 0.1711(4) 0.0193(9) Uani 1.0 4 d . . . O4 O 0.1224(7) -0.3611(5) 0.3341(4) 0.0198(8) Uani 1.0 4 d . . . C5 C 0.1060(10) -0.2714(7) 0.2125(5) 0.0154(11) Uani 1.0 4 d . . . C6 C 0.3015(12) -0.3136(9) 0.1098(7) 0.0203(12) Uani 1.0 4 d . . . H7 H 0.284(11) -0.443(8) 0.082(6) 0.016(14) Uiso 1.0 4 d . . . H8 H 0.432(11) -0.261(8) 0.160(6) 0.012(15) Uiso 1.0 4 d . . . H9 H 0.362(12) -0.195(8) -0.058(7) 0.021(16) Uiso 1.0 4 d . . . 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 Cu1 0.0166(6) 0.0185(5) 0.0157(6) 0.0018(4) 0.0091(4) 0.0024(4) O2 0.018(2) 0.024(2) 0.0179(19) 0.0052(16) 0.0115(16) 0.0047(15) O3 0.018(2) 0.022(2) 0.020(2) 0.0023(16) 0.0097(15) 0.0021(16) O4 0.019(2) 0.025(2) 0.0173(19) 0.0050(16) 0.0071(15) 0.0083(16) C5 0.010(3) 0.025(3) 0.012(3) -0.001(2) 0.0041(19) -0.003(3) C6 0.019(3) 0.024(3) 0.021(3) 0.006(3) 0.011(3) 0.006(3) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution SIR97 _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 Cu1 O2 1.959(4) yes . . Cu1 O2 1.959(4) yes . 3_555 Cu1 O3 1.934(4) yes . . Cu1 O3 1.934(4) yes . 3_555 O2 C6 1.431(7) yes . . O3 C5 1.261(6) yes . . O4 C5 1.248(6) yes . . C5 C6 1.516(9) yes . . O2 H9 0.78(7) no . . C6 H7 0.97(6) no . . C6 H8 0.83(5) 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 O2 Cu1 O2 180.0(2) yes . . 3_555 O2 Cu1 O3 83.12(16) yes . . . O2 Cu1 O3 96.88(16) yes . . 3_555 O2 Cu1 O3 96.88(16) yes 3_555 . . O2 Cu1 O3 83.12(16) yes 3_555 . 3_555 O3 Cu1 O3 180.0(2) yes . . 3_555 Cu1 O2 C6 111.3(4) yes . . . Cu1 O3 C5 113.9(4) yes . . . O3 C5 O4 123.4(5) yes . . . O3 C5 C6 118.4(5) yes . . . O4 C5 C6 118.2(5) yes . . . O2 C6 C5 108.4(5) yes . . . Cu1 O2 H9 123(5) no . . . C6 O2 H9 105(4) no . . . O2 C6 H7 108(3) no . . . O2 C6 H8 105(4) no . . . C5 C6 H7 108(4) no . . . C5 C6 H8 99(4) no . . . H7 C6 H8 127(5) 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 O2 Cu1 O3 C5 17.5(3) no . . . . O3 Cu1 O2 C6 -20.0(2) no . . . . O2 Cu1 O3 C5 162.5(3) no . . 3_555 3_555 O3 Cu1 O2 C6 160.0(2) no 3_555 . . . O2 Cu1 O3 C5 -162.5(3) no 3_555 . . . O3 Cu1 O2 C6 -160.0(2) no . . 3_555 3_555 O2 Cu1 O3 C5 -17.5(3) no 3_555 . 3_555 3_555 O3 Cu1 O2 C6 20.0(2) no 3_555 . 3_555 3_555 Cu1 O2 C6 C5 18.6(5) no . . . . Cu1 O3 C5 O4 168.5(4) no . . . . Cu1 O3 C5 C6 -11.2(5) no . . . . O3 C5 C6 O2 -5.2(6) no . . . . O4 C5 C6 O2 175.0(4) 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 Cu1 C5 2.703(5) no . 3_555 Cu1 C6 2.815(6) no . 3_555 O2 O4 3.547(6) no . . Cu1 O4 2.432(4) no . 2_555 Cu1 O4 2.432(4) no . 4_444 Cu1 C5 3.383(5) no . 2_555 Cu1 C5 3.383(5) no . 4_444 O2 O3 3.233(6) no . 4_544 O2 O4 3.044(6) no . 2_555 O2 O4 3.200(6) no . 4_444 O2 O4 2.604(6) no . 4_544 O2 C5 3.286(7) no . 4_544 O2 C6 3.558(7) no . 4_444 O3 O2 3.233(6) no . 4_445 O3 O4 3.544(6) no . 2_455 O3 O4 3.088(6) no . 2_555 O3 O4 3.127(5) no . 4_444 O3 C6 3.441(8) no . 1_455 O3 C6 3.231(7) no . 2_555 O4 Cu1 2.432(4) no . 2_545 O4 O2 3.044(6) no . 2_545 O4 O2 2.604(6) no . 4_445 O4 O2 3.200(6) no . 4_545 O4 O3 3.544(6) no . 2_445 O4 O3 3.088(6) no . 2_545 O4 O3 3.127(5) no . 4_545 O4 C5 3.334(7) no . 2_545 O4 C6 3.311(8) no . 2_545 O4 C6 3.448(8) no . 4_445 C5 Cu1 3.383(5) no . 2_545 C5 O2 3.286(7) no . 4_445 C5 O4 3.334(7) no . 2_555 C6 O2 3.558(7) no . 4_545 C6 O3 3.441(8) no . 1_655 C6 O3 3.231(7) no . 2_545 C6 O4 3.311(8) no . 2_555 C6 O4 3.448(8) no . 4_544 Cu1 H7 3.54(6) no . . Cu1 H7 3.54(6) no . 3_555 Cu1 H8 3.06(5) no . . Cu1 H8 3.06(5) no . 3_555 Cu1 H9 2.47(6) no . 3_555 O3 H7 2.99(6) no . . O3 H8 2.72(6) no . . O3 H9 3.29(7) no . . O3 H9 2.98(6) no . 3_555 O4 H7 2.60(6) no . . O4 H8 2.53(6) no . . C5 H9 3.01(6) no . . H7 H9 2.26(8) no . . H8 H9 1.96(8) no . . Cu1 H8 3.44(5) no . 2_555 Cu1 H8 3.44(5) no . 4_444 Cu1 H9 3.54(6) no . 1_455 Cu1 H9 3.54(6) no . 3_655 O2 H8 2.92(5) no . 4_444 O2 H9 3.58(6) no . 3_655 O3 H7 2.81(5) no . 2_555 O3 H8 2.72(6) no . 1_455 O3 H8 3.17(6) no . 2_555 O3 H9 3.29(6) no . 1_455 O3 H9 2.75(6) no . 4_445 O4 H7 3.12(6) no . 2_555 O4 H8 2.90(6) no . 2_545 O4 H8 3.35(6) no . 4_445 O4 H9 3.11(6) no . 2_545 O4 H9 1.84(7) no . 4_445 C5 H7 2.98(6) no . 2_555 C5 H8 3.43(6) no . 1_455 C5 H9 2.60(7) no . 4_445 C6 H7 3.46(6) no . 3_645 H7 O3 2.81(5) no . 2_545 H7 O4 3.12(6) no . 2_545 H7 C5 2.98(6) no . 2_545 H7 C6 3.46(6) no . 3_645 H7 H7 3.14(7) no . 3_545 H7 H7 3.01(8) no . 3_645 H7 H8 3.57(8) no . 2_545 H7 H8 3.54(8) no . 3_645 H7 H9 3.22(8) no . 3_645 H8 Cu1 3.44(5) no . 2_545 H8 O2 2.92(5) no . 4_545 H8 O3 2.72(6) no . 1_655 H8 O3 3.17(6) no . 2_545 H8 O4 2.90(6) no . 2_555 H8 O4 3.35(6) no . 4_544 H8 C5 3.43(6) no . 1_655 H8 H7 3.57(8) no . 2_555 H8 H7 3.54(8) no . 3_645 H8 H9 3.04(7) no . 4_545 H9 Cu1 3.54(6) no . 1_655 H9 O2 3.58(6) no . 3_655 H9 O3 3.29(6) no . 1_655 H9 O3 2.75(6) no . 4_544 H9 O4 3.11(6) no . 2_555 H9 O4 1.84(7) no . 4_544 H9 C5 2.60(7) no . 4_544 H9 H7 3.22(8) no . 3_645 H9 H8 3.04(7) no . 4_444 H9 H9 3.23(8) no . 3_655 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H9 O4 . . 4_544 2.604(6) 0.779 1.84(7) 167(6) no #============================================================================== # 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 950567' ####################################################################### # # 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_13042302_250K01 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C4 H6 Cu O6' _chemical_formula_moiety 'C4 H6 Cu O6' _chemical_formula_weight 213.63 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 5.0908(8) _cell_length_b 8.6939(12) _cell_length_c 7.7300(14) _cell_angle_alpha 90.0000 _cell_angle_beta 107.141(8) _cell_angle_gamma 90.0000 _cell_volume 326.93(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 900 _cell_measurement_theta_min 3.60 _cell_measurement_theta_max 27.40 _cell_measurement_temperature 249 #------------------------------------------------------------------------------ _exptl_crystal_description unknown _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 2.170 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 214.00 _exptl_absorpt_coefficient_mu 3.319 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.528 _exptl_absorpt_correction_T_max 0.718 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 249 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.706 _diffrn_reflns_number 2360 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_theta_max 27.42 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _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 743 _reflns_number_gt 647 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0640 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refxyz _refine_ls_number_reflns 743 _refine_ls_number_parameters 64 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0280P)^2^+0.0783P] 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 0.000 _refine_diff_density_max 0.290 _refine_diff_density_min -0.330 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 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) ; Cu Cu 0.3201 1.2651 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; 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 Cu1 Cu 0.0000 0.0000 0.0000 0.02073(16) Uani 1.0 2 d . . . O2 O 0.0475(4) -0.16119(19) -0.1583(3) 0.0239(4) Uani 1.0 4 d . . . O3 O -0.2418(4) -0.1474(2) 0.0626(3) 0.0248(4) Uani 1.0 4 d . . . O4 O -0.0897(4) -0.39576(19) -0.2571(3) 0.0256(4) Uani 1.0 4 d . . . C5 C -0.0923(5) -0.2818(3) -0.1587(3) 0.0189(5) Uani 1.0 4 d . . . C6 C -0.2678(6) -0.2892(3) -0.0313(4) 0.0240(6) Uani 1.0 4 d . . . H7 H -0.441(7) -0.311(4) -0.094(5) 0.037(8) Uiso 1.0 4 d . . . H8 H -0.213(6) -0.369(3) 0.042(4) 0.023(7) Uiso 1.0 4 d . . . H9 H -0.341(6) -0.134(4) 0.104(4) 0.028(9) Uiso 1.0 4 d . . . 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 Cu1 0.0272(3) 0.0170(3) 0.0256(3) -0.00253(15) 0.01959(17) -0.00284(15) O2 0.0310(9) 0.0211(10) 0.0278(9) -0.0035(7) 0.0215(8) -0.0032(7) O3 0.0319(10) 0.0219(10) 0.0309(10) -0.0049(8) 0.0253(9) -0.0057(7) O4 0.0307(9) 0.0242(10) 0.0288(9) -0.0057(7) 0.0193(8) -0.0088(7) C5 0.0190(11) 0.0224(13) 0.0178(11) 0.0024(9) 0.0095(9) 0.0012(9) C6 0.0299(13) 0.0218(14) 0.0268(13) -0.0072(11) 0.0185(11) -0.0050(11) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution SIR97 _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 Cu1 O2 1.9222(18) yes . . Cu1 O2 1.9222(18) yes . 3_555 Cu1 O3 1.935(2) yes . . Cu1 O3 1.935(2) yes . 3_555 O2 C5 1.266(3) yes . . O3 C6 1.416(4) yes . . O4 C5 1.252(3) yes . . C5 C6 1.514(4) yes . . O3 H9 0.69(4) no . . C6 H7 0.89(3) no . . C6 H8 0.89(3) 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 O2 Cu1 O2 180.00(10) yes . . 3_555 O2 Cu1 O3 83.40(8) yes . . . O2 Cu1 O3 96.60(8) yes . . 3_555 O2 Cu1 O3 96.60(8) yes 3_555 . . O2 Cu1 O3 83.40(8) yes 3_555 . 3_555 O3 Cu1 O3 180.00(11) yes . . 3_555 Cu1 O2 C5 115.40(17) yes . . . Cu1 O3 C6 114.73(18) yes . . . O2 C5 O4 123.4(3) yes . . . O2 C5 C6 118.2(2) yes . . . O4 C5 C6 118.4(3) yes . . . O3 C6 C5 108.2(3) yes . . . Cu1 O3 H9 128(3) no . . . C6 O3 H9 114(3) no . . . O3 C6 H7 113(2) no . . . O3 C6 H8 112.9(18) no . . . C5 C6 H7 110(3) no . . . C5 C6 H8 108(2) no . . . H7 C6 H8 104(3) 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 O2 Cu1 O3 C6 -0.69(10) no . . . . O3 Cu1 O2 C5 1.91(11) no . . . . O2 Cu1 O3 C6 -179.31(10) no . . 3_555 3_555 O3 Cu1 O2 C5 -178.09(11) no 3_555 . . . O2 Cu1 O3 C6 179.31(10) no 3_555 . . . O3 Cu1 O2 C5 178.09(11) no . . 3_555 3_555 O2 Cu1 O3 C6 0.69(10) no 3_555 . 3_555 3_555 O3 Cu1 O2 C5 -1.91(11) no 3_555 . 3_555 3_555 Cu1 O2 C5 O4 178.31(13) no . . . . Cu1 O2 C5 C6 -2.7(2) no . . . . Cu1 O3 C6 C5 -0.4(2) no . . . . O2 C5 C6 O3 2.0(3) no . . . . O4 C5 C6 O3 -178.94(17) 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 Cu1 C5 2.718(3) no . 3_555 Cu1 C6 2.836(3) no . 3_555 O3 O4 3.535(3) no . . Cu1 O4 2.5292(16) no . 2_454 Cu1 O4 2.5292(16) no . 4_545 Cu1 C5 3.412(2) no . 2_454 Cu1 C5 3.412(2) no . 4_545 O2 O3 3.518(3) no . 1_655 O2 O3 3.152(3) no . 4_544 O2 O4 3.207(3) no . 2_454 O2 O4 3.146(3) no . 4_545 O2 C6 3.512(4) no . 1_655 O2 C6 3.313(4) no . 4_544 O3 O2 3.518(3) no . 1_455 O3 O2 3.152(3) no . 4_445 O3 O3 3.594(3) no . 3_455 O3 O4 3.147(3) no . 2_454 O3 O4 2.584(3) no . 4_445 O3 O4 3.221(3) no . 4_545 O3 C5 3.235(4) no . 4_445 O3 C5 3.429(3) no . 4_545 O3 C6 3.394(3) no . 4_545 O4 Cu1 2.5292(16) no . 2_444 O4 O2 3.207(3) no . 2_444 O4 O2 3.146(3) no . 4_444 O4 O3 3.147(3) no . 2_444 O4 O3 3.221(3) no . 4_444 O4 O3 2.584(3) no . 4_544 O4 C6 3.436(4) no . 4_544 C5 Cu1 3.412(2) no . 2_444 C5 O3 3.429(3) no . 4_444 C5 O3 3.235(4) no . 4_544 C6 O2 3.512(4) no . 1_455 C6 O2 3.313(4) no . 4_445 C6 O3 3.394(3) no . 4_444 C6 O4 3.436(4) no . 4_445 Cu1 H7 3.46(3) no . . Cu1 H7 3.46(3) no . 3_555 Cu1 H8 3.43(3) no . . Cu1 H8 3.43(3) no . 3_555 Cu1 H9 2.42(4) no . 3_555 O2 H7 2.98(4) no . . O2 H8 2.94(3) no . . O2 H9 3.23(4) no . . O2 H9 2.94(3) no . 3_555 O4 H7 2.58(4) no . . O4 H8 2.58(3) no . . C5 H9 2.98(4) no . . H7 H9 2.12(4) no . . H8 H9 2.24(4) no . . Cu1 H7 3.48(4) no . 2_454 Cu1 H7 3.48(4) no . 4_545 Cu1 H9 3.41(3) no . 1_655 Cu1 H9 3.41(3) no . 3_455 O2 H7 2.82(4) no . 1_655 O2 H7 3.55(3) no . 2_454 O2 H7 3.39(4) no . 4_544 O2 H8 2.93(4) no . 4_544 O2 H9 3.18(3) no . 1_655 O2 H9 2.73(4) no . 4_544 O3 H7 2.67(3) no . 4_545 O3 H9 3.25(3) no . 3_455 O4 H7 3.25(3) no . 1_655 O4 H7 3.43(4) no . 4_544 O4 H8 2.79(3) no . 3_545 O4 H9 3.33(3) no . 2_444 O4 H9 1.90(4) no . 4_544 C5 H7 3.21(4) no . 1_655 C5 H8 3.41(3) no . 3_545 C5 H8 3.57(3) no . 4_444 C5 H9 2.63(4) no . 4_544 C6 H7 3.41(3) no . 4_545 C6 H9 3.47(3) no . 4_444 H7 Cu1 3.48(4) no . 2_444 H7 O2 2.82(4) no . 1_455 H7 O2 3.55(3) no . 2_444 H7 O2 3.39(4) no . 4_445 H7 O3 2.67(3) no . 4_444 H7 O4 3.25(3) no . 1_455 H7 O4 3.43(4) no . 4_445 H7 C5 3.21(4) no . 1_455 H7 C6 3.41(3) no . 4_444 H7 H8 3.37(5) no . 3_445 H7 H8 3.16(4) no . 4_444 H7 H9 2.65(4) no . 4_444 H8 O2 2.93(4) no . 4_445 H8 O4 2.79(3) no . 3_545 H8 C5 3.41(3) no . 3_545 H8 C5 3.57(3) no . 4_545 H8 H7 3.37(5) no . 3_445 H8 H7 3.16(4) no . 4_545 H8 H8 3.34(4) no . 3_545 H8 H9 3.52(4) no . 2_445 H9 Cu1 3.41(3) no . 1_455 H9 O2 3.18(3) no . 1_455 H9 O2 2.73(4) no . 4_445 H9 O3 3.25(3) no . 3_455 H9 O4 3.33(3) no . 2_454 H9 O4 1.90(4) no . 4_445 H9 C5 2.63(4) no . 4_445 H9 C6 3.47(3) no . 4_545 H9 H7 2.65(4) no . 4_545 H9 H8 3.52(4) no . 2_455 H9 H9 3.02(4) no . 3_455 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O3 H9 O4 . . 4_445 2.584(3) 0.685 1.90(4) 174(3) no #============================================================================== # 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 950568'