# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Aakeroy, C.' 'Sinha, Abhijeet' 'Chopade, Prashant' 'Desper, John' _publ_contact_author_name 'Aakeroy, C.' _publ_contact_author_email aakeroy@ksu.edu _publ_section_title ; Halogen bonding or close packing? Examining the structural landscape in a series of Cu(II)-acac complexes ; # Attachment '- all(1).cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 826234' #TrackingRef '- all(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AS-15 2-(4-tolyl)-2,4-pentanedione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 O2' _chemical_formula_sum 'C12 H14 O2' _chemical_formula_weight 190.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 7.5220(8) _cell_length_b 6.6202(7) _cell_length_c 11.1582(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.875(4) _cell_angle_gamma 90.00 _cell_volume 525.77(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2944 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 32.49 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9747 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7020 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 32.56 _reflns_number_total 2027 _reflns_number_gt 1603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2027 _refine_ls_number_parameters 84 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1972 _refine_ls_wR_factor_gt 0.1829 _refine_ls_goodness_of_fit_ref 1.377 _refine_ls_restrained_S_all 1.377 _refine_ls_shift/su_max 0.000 _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 C11 C -0.2761(2) 0.2500 0.26429(16) 0.0395(4) Uani 1 2 d S . . H11A H -0.3850 0.1731 0.2689 0.059 Uiso 0.50 1 calc PR . . H11B H -0.2268 0.1876 0.2019 0.059 Uiso 0.50 1 calc PR . . H11C H -0.3142 0.3893 0.2389 0.059 Uiso 0.50 1 calc PR . . C12 C -0.12755(18) 0.2500 0.39085(14) 0.0298(3) Uani 1 2 d S . . O12 O -0.18571(15) 0.2500 0.48786(11) 0.0369(3) Uani 1 2 d S . . H12 H -0.044(3) 0.2500 0.5759(18) 0.044 Uiso 1 2 d S . . C13 C 0.06616(17) 0.2500 0.40524(12) 0.0236(3) Uani 1 2 d S . . C14 C 0.19625(18) 0.2500 0.52809(12) 0.0247(3) Uani 1 2 d S . . O14 O 0.14181(15) 0.2500 0.62737(9) 0.0331(3) Uani 1 2 d S . . C15 C 0.4040(2) 0.2500 0.55498(14) 0.0329(3) Uani 1 2 d S . . H15A H 0.4331 0.1947 0.4820 0.049 Uiso 0.50 1 calc PR . . H15B H 0.4638 0.1666 0.6298 0.049 Uiso 0.50 1 calc PR . . H15C H 0.4515 0.3886 0.5709 0.049 Uiso 0.50 1 calc PR . . C21 C 0.12929(17) 0.2500 0.29106(11) 0.0234(3) Uani 1 2 d S . . C22 C 0.15964(19) 0.07116(15) 0.23592(11) 0.0392(3) Uani 1 1 d . . . H22 H 0.1433 -0.0541 0.2726 0.047 Uiso 1 1 calc R . . C23 C 0.2136(2) 0.07191(16) 0.12777(11) 0.0428(3) Uani 1 1 d . . . H23 H 0.2321 -0.0530 0.0916 0.051 Uiso 1 1 calc R . . C24 C 0.2409(2) 0.2500 0.07185(12) 0.0301(3) Uani 1 2 d S . . C27 C 0.3019(3) 0.2500 -0.04453(15) 0.0446(4) Uani 1 2 d S . . H27A H 0.3165 0.3896 -0.0691 0.067 Uiso 0.50 1 calc PR . . H27B H 0.2068 0.1816 -0.1141 0.067 Uiso 0.50 1 calc PR . . H27C H 0.4221 0.1789 -0.0259 0.067 Uiso 0.50 1 calc PR . . 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 C11 0.0242(6) 0.0388(8) 0.0511(9) 0.000 0.0059(6) 0.000 C12 0.0261(6) 0.0201(6) 0.0449(8) 0.000 0.0138(5) 0.000 O12 0.0336(6) 0.0344(6) 0.0517(7) 0.000 0.0263(5) 0.000 C13 0.0240(6) 0.0198(5) 0.0289(6) 0.000 0.0112(5) 0.000 C14 0.0297(6) 0.0197(5) 0.0264(6) 0.000 0.0114(5) 0.000 O14 0.0433(6) 0.0318(5) 0.0298(5) 0.000 0.0196(4) 0.000 C15 0.0281(6) 0.0377(7) 0.0315(6) 0.000 0.0078(5) 0.000 C21 0.0221(5) 0.0231(5) 0.0240(5) 0.000 0.0062(4) 0.000 C22 0.0635(7) 0.0218(5) 0.0423(6) -0.0009(4) 0.0309(5) -0.0025(4) C23 0.0702(8) 0.0262(5) 0.0423(6) -0.0063(4) 0.0324(6) -0.0036(5) C24 0.0343(7) 0.0328(7) 0.0220(6) 0.000 0.0076(5) 0.000 C27 0.0653(11) 0.0444(9) 0.0299(7) 0.000 0.0236(7) 0.000 _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 C11 C12 1.491(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O12 1.2921(16) . ? C12 C13 1.4134(18) . ? O12 H12 1.19(2) . ? C13 C14 1.4031(19) . ? C13 C21 1.4967(16) . ? C14 O14 1.2994(15) . ? C14 C15 1.4930(19) . ? O14 H12 1.33(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C21 C22 1.3868(12) . ? C21 C22 1.3868(12) 4_565 ? C22 C23 1.3921(14) . ? C22 H22 0.9500 . ? C23 C24 1.3799(13) . ? C23 H23 0.9500 . ? C24 C23 1.3799(13) 4_565 ? C24 C27 1.5109(19) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O12 C12 C13 121.39(13) . . ? O12 C12 C11 116.13(12) . . ? C13 C12 C11 122.48(13) . . ? C12 O12 H12 103.7(9) . . ? C14 C13 C12 118.59(12) . . ? C14 C13 C21 121.24(11) . . ? C12 C13 C21 120.17(11) . . ? O14 C14 C13 121.36(11) . . ? O14 C14 C15 115.26(11) . . ? C13 C14 C15 123.38(11) . . ? C14 O14 H12 102.1(8) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C22 C21 C22 117.23(12) . 4_565 ? C22 C21 C13 121.38(6) . . ? C22 C21 C13 121.38(6) 4_565 . ? C21 C22 C23 121.17(9) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 121.51(9) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C23 C24 C23 117.38(12) 4_565 . ? C23 C24 C27 121.31(6) 4_565 . ? C23 C24 C27 121.31(6) . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 O12 C12 C13 C14 0.0 . . . . ? C11 C12 C13 C14 180.0 . . . . ? O12 C12 C13 C21 180.0 . . . . ? C11 C12 C13 C21 0.0 . . . . ? C12 C13 C14 O14 0.0 . . . . ? C21 C13 C14 O14 180.0 . . . . ? C12 C13 C14 C15 180.0 . . . . ? C21 C13 C14 C15 0.0 . . . . ? C14 C13 C21 C22 90.04(11) . . . . ? C12 C13 C21 C22 -89.96(11) . . . . ? C14 C13 C21 C22 -90.04(11) . . . 4_565 ? C12 C13 C21 C22 89.96(11) . . . 4_565 ? C22 C21 C22 C23 -1.6(2) 4_565 . . . ? C13 C21 C22 C23 178.30(11) . . . . ? C21 C22 C23 C24 0.7(2) . . . . ? C22 C23 C24 C23 0.4(3) . . . 4_565 ? C22 C23 C24 C27 179.18(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H12 O14 1.19(2) 1.33(2) 2.4518(15) 152.9(17) . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 32.56 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.350 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.054 #END data_3 _database_code_depnum_ccdc_archive 'CCDC 826235' #TrackingRef '- all(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AS-14 2-(4-chlorophenyl)-2,4-pentanedione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Cl O2' _chemical_formula_sum 'C11 H11 Cl O2' _chemical_formula_weight 210.65 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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 20.2258(14) _cell_length_b 6.7622(5) _cell_length_c 7.3688(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1007.84(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5158 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 33.38 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.348 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9089 _exptl_absorpt_correction_T_max 0.9595 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19595 _diffrn_reflns_av_R_equivalents 0.0638 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 33.65 _reflns_number_total 2140 _reflns_number_gt 1794 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0650P)^2^+0.2500P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2140 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 Cl1 Cl 0.452060(18) 0.2500 0.12844(6) 0.03715(14) Uani 1 2 d S . . C11 C 0.63539(8) 0.2500 0.89336(19) 0.0294(3) Uani 1 2 d S . . H11A H 0.6405 0.1545 0.9924 0.044 Uiso 0.50 1 calc PR . . H11B H 0.5973 0.2131 0.8186 0.044 Uiso 0.50 1 calc PR . . H11C H 0.6284 0.3824 0.9440 0.044 Uiso 0.50 1 calc PR . . C12 C 0.69630(7) 0.2500 0.77925(18) 0.0223(2) Uani 1 2 d S . . O12 O 0.75175(6) 0.2500 0.87315(15) 0.0298(3) Uani 1 2 d S . . H12 H 0.7853(10) 0.2500 0.780(3) 0.036 Uiso 1 2 d S . . C13 C 0.69696(6) 0.2500 0.59116(17) 0.0194(2) Uani 1 2 d S . . C14 C 0.75970(6) 0.2500 0.49952(18) 0.0221(3) Uani 1 2 d S . . O14 O 0.81355(5) 0.2500 0.58765(15) 0.0324(3) Uani 1 2 d S . . C15 C 0.76290(7) 0.2500 0.29640(19) 0.0255(3) Uani 1 2 d S . . H15A H 0.7326 0.3504 0.2484 0.038 Uiso 0.50 1 calc PR . . H15B H 0.7500 0.1195 0.2505 0.038 Uiso 0.50 1 calc PR . . H15C H 0.8081 0.2800 0.2574 0.038 Uiso 0.50 1 calc PR . . C21 C 0.63494(6) 0.2500 0.48223(16) 0.0177(2) Uani 1 2 d S . . C22 C 0.60582(5) 0.07357(15) 0.42731(16) 0.0287(2) Uani 1 1 d . . . H22 H 0.6247 -0.0485 0.4645 0.034 Uiso 1 1 calc R . . C23 C 0.54947(5) 0.07255(17) 0.31888(18) 0.0321(2) Uani 1 1 d . . . H23 H 0.5301 -0.0490 0.2820 0.039 Uiso 1 1 calc R . . C24 C 0.52200(6) 0.2500 0.26559(19) 0.0240(3) Uani 1 2 d S . . 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 0.02092(18) 0.0608(3) 0.0297(2) 0.000 -0.00905(12) 0.000 C11 0.0258(6) 0.0448(8) 0.0177(6) 0.000 0.0049(5) 0.000 C12 0.0210(5) 0.0294(6) 0.0166(5) 0.000 0.0002(4) 0.000 O12 0.0238(5) 0.0499(7) 0.0158(4) 0.000 -0.0034(4) 0.000 C13 0.0172(5) 0.0261(6) 0.0150(5) 0.000 0.0000(4) 0.000 C14 0.0184(5) 0.0315(7) 0.0165(5) 0.000 0.0000(4) 0.000 O14 0.0167(5) 0.0589(8) 0.0214(5) 0.000 -0.0012(4) 0.000 C15 0.0235(6) 0.0366(7) 0.0166(6) 0.000 0.0035(5) 0.000 C21 0.0159(5) 0.0226(5) 0.0146(5) 0.000 0.0006(4) 0.000 C22 0.0266(4) 0.0211(4) 0.0383(6) -0.0022(4) -0.0104(4) 0.0014(3) C23 0.0268(5) 0.0289(5) 0.0407(6) -0.0079(4) -0.0111(4) -0.0022(4) C24 0.0161(5) 0.0371(7) 0.0189(6) 0.000 -0.0016(4) 0.000 _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 C24 1.7385(14) . ? C11 C12 1.4916(19) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O12 1.3178(16) . ? C12 C13 1.3861(18) . ? O12 H12 0.97(2) . ? C13 C14 1.4374(18) . ? C13 C21 1.4894(17) . ? C14 O14 1.2679(16) . ? C14 C15 1.4981(19) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C21 C22 1.3907(12) . ? C21 C22 1.3907(12) 7_565 ? C22 C23 1.3919(14) . ? C22 H22 0.9500 . ? C23 C24 1.3794(13) . ? C23 H23 0.9500 . ? C24 C23 1.3794(13) 7_565 ? 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 C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O12 C12 C13 121.12(12) . . ? O12 C12 C11 114.01(12) . . ? C13 C12 C11 124.87(12) . . ? C12 O12 H12 102.9(13) . . ? C12 C13 C14 118.58(12) . . ? C12 C13 C21 122.06(12) . . ? C14 C13 C21 119.37(11) . . ? O14 C14 C13 121.17(12) . . ? O14 C14 C15 118.34(12) . . ? C13 C14 C15 120.49(11) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C22 C21 C22 118.16(12) . 7_565 ? C22 C21 C13 120.90(6) . . ? C22 C21 C13 120.90(6) 7_565 . ? C21 C22 C23 121.20(10) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 119.27(10) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C23 120.90(13) 7_565 . ? C23 C24 Cl1 119.55(6) 7_565 . ? C23 C24 Cl1 119.55(6) . . ? 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 O12 C12 C13 C14 0.0 . . . . ? C11 C12 C13 C14 180.0 . . . . ? O12 C12 C13 C21 180.0 . . . . ? C11 C12 C13 C21 0.0 . . . . ? C12 C13 C14 O14 0.0 . . . . ? C21 C13 C14 O14 180.0 . . . . ? C12 C13 C14 C15 180.0 . . . . ? C21 C13 C14 C15 0.0 . . . . ? C12 C13 C21 C22 -91.13(11) . . . . ? C14 C13 C21 C22 88.87(11) . . . . ? C12 C13 C21 C22 91.13(11) . . . 7_565 ? C14 C13 C21 C22 -88.87(11) . . . 7_565 ? C22 C21 C22 C23 0.6(2) 7_565 . . . ? C13 C21 C22 C23 -177.18(11) . . . . ? C21 C22 C23 C24 -0.2(2) . . . . ? C22 C23 C24 C23 -0.3(2) . . . 7_565 ? C22 C23 C24 Cl1 179.42(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H12 O14 0.97(2) 1.53(2) 2.4471(16) 157(2) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 33.65 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.482 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.058 #END data_4 _database_code_depnum_ccdc_archive 'CCDC 826236' #TrackingRef '- all(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AS-5 2-(4-bromophenyl)-2,4-pentanedione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Br O2' _chemical_formula_sum 'C11 H11 Br O2' _chemical_formula_weight 255.11 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 20.4766(18) _cell_length_b 6.8070(6) _cell_length_c 7.3506(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1024.56(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8388 _cell_measurement_theta_min 3.98 _cell_measurement_theta_max 32.16 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 3.982 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4019 _exptl_absorpt_correction_T_max 0.6465 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29950 _diffrn_reflns_av_R_equivalents 0.0694 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 33.68 _reflns_number_total 2184 _reflns_number_gt 1744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0250P)^2^+0.4500P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2184 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _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 Br1 Br 0.449955(9) 0.2500 0.12625(3) 0.02954(7) Uani 1 2 d S . . C11 C 0.63905(9) 0.2500 0.9021(2) 0.0261(4) Uani 1 2 d S . . H11A H 0.6437 0.1508 0.9979 0.039 Uiso 0.50 1 calc PR . . H11B H 0.6008 0.2194 0.8274 0.039 Uiso 0.50 1 calc PR . . H11C H 0.6335 0.3798 0.9577 0.039 Uiso 0.50 1 calc PR . . C12 C 0.69850(8) 0.2500 0.7861(2) 0.0204(3) Uani 1 2 d S . . O12 O 0.75364(7) 0.2500 0.87878(18) 0.0263(3) Uani 1 2 d S . . H12 H 0.7838(14) 0.2500 0.815(4) 0.032 Uiso 1 2 d S . . C13 C 0.69848(8) 0.2500 0.5980(2) 0.0186(3) Uani 1 2 d S . . C14 C 0.75991(9) 0.2500 0.5044(2) 0.0212(3) Uani 1 2 d S . . O14 O 0.81340(7) 0.2500 0.58995(18) 0.0284(3) Uani 1 2 d S . . C15 C 0.76186(9) 0.2500 0.3007(2) 0.0238(3) Uani 1 2 d S . . H15A H 0.7315 0.3491 0.2540 0.036 Uiso 0.50 1 calc PR . . H15B H 0.7492 0.1201 0.2553 0.036 Uiso 0.50 1 calc PR . . H15C H 0.8062 0.2808 0.2595 0.036 Uiso 0.50 1 calc PR . . C21 C 0.63696(8) 0.2500 0.4908(2) 0.0175(3) Uani 1 2 d S . . C22 C 0.60813(6) 0.07443(19) 0.43657(18) 0.0236(2) Uani 1 1 d . . . H22 H 0.6268 -0.0467 0.4742 0.028 Uiso 1 1 calc R . . C23 C 0.55243(6) 0.0732(2) 0.3283(2) 0.0255(2) Uani 1 1 d . . . H23 H 0.5333 -0.0475 0.2914 0.031 Uiso 1 1 calc R . . C24 C 0.52535(8) 0.2500 0.2751(2) 0.0213(3) Uani 1 2 d S . . 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 Br1 0.01833(9) 0.04539(13) 0.02490(10) 0.000 -0.00675(6) 0.000 C11 0.0219(8) 0.0390(10) 0.0175(8) 0.000 0.0034(6) 0.000 C12 0.0203(7) 0.0254(8) 0.0154(7) 0.000 -0.0002(6) 0.000 O12 0.0215(6) 0.0421(8) 0.0154(5) 0.000 -0.0025(5) 0.000 C13 0.0161(7) 0.0251(8) 0.0144(7) 0.000 -0.0009(5) 0.000 C14 0.0189(7) 0.0286(9) 0.0162(7) 0.000 0.0000(6) 0.000 O14 0.0160(6) 0.0488(9) 0.0205(6) 0.000 -0.0011(5) 0.000 C15 0.0207(8) 0.0356(10) 0.0151(7) 0.000 0.0028(6) 0.000 C21 0.0145(6) 0.0243(8) 0.0138(6) 0.000 0.0002(5) 0.000 C22 0.0226(5) 0.0220(5) 0.0263(6) -0.0003(5) -0.0050(5) 0.0017(5) C23 0.0223(5) 0.0255(6) 0.0287(6) -0.0042(5) -0.0041(5) -0.0019(5) C24 0.0145(7) 0.0335(9) 0.0158(7) 0.000 -0.0009(5) 0.000 _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 Br1 C24 1.8923(17) . ? C11 C12 1.486(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O12 1.319(2) . ? C12 C13 1.382(2) . ? O12 H12 0.78(3) . ? C13 C14 1.434(2) . ? C13 C21 1.486(2) . ? C14 O14 1.263(2) . ? C14 C15 1.498(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C21 C22 1.3913(15) . ? C21 C22 1.3913(15) 7_565 ? C22 C23 1.3908(18) . ? C22 H22 0.9500 . ? C23 C24 1.3817(16) . ? C23 H23 0.9500 . ? C24 C23 1.3817(16) 7_565 ? 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 C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O12 C12 C13 121.12(16) . . ? O12 C12 C11 113.88(15) . . ? C13 C12 C11 125.00(16) . . ? C12 O12 H12 112(2) . . ? C12 C13 C14 118.68(16) . . ? C12 C13 C21 122.06(16) . . ? C14 C13 C21 119.26(14) . . ? O14 C14 C13 121.43(15) . . ? O14 C14 C15 118.34(16) . . ? C13 C14 C15 120.22(15) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C22 C21 C22 118.41(15) . 7_565 ? C22 C21 C13 120.78(8) . . ? C22 C21 C13 120.78(8) 7_565 . ? C23 C22 C21 121.14(13) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 119.05(13) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C23 C24 C23 121.19(16) 7_565 . ? C23 C24 Br1 119.41(8) 7_565 . ? C23 C24 Br1 119.41(8) . . ? 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 O12 C12 C13 C14 0.0 . . . . ? C11 C12 C13 C14 180.0 . . . . ? O12 C12 C13 C21 180.0 . . . . ? C11 C12 C13 C21 0.0 . . . . ? C12 C13 C14 O14 0.0 . . . . ? C21 C13 C14 O14 180.0 . . . . ? C12 C13 C14 C15 180.0 . . . . ? C21 C13 C14 C15 0.0 . . . . ? C12 C13 C21 C22 -91.17(14) . . . . ? C14 C13 C21 C22 88.83(14) . . . . ? C12 C13 C21 C22 91.17(14) . . . 7_565 ? C14 C13 C21 C22 -88.83(14) . . . 7_565 ? C22 C21 C22 C23 1.1(3) 7_565 . . . ? C13 C21 C22 C23 -176.66(14) . . . . ? C21 C22 C23 C24 -0.4(2) . . . . ? C22 C23 C24 C23 -0.3(3) . . . 7_565 ? C22 C23 C24 Br1 179.52(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H12 O14 0.78(3) 1.76(3) 2.451(2) 147(3) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 33.68 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.632 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.071 #END data_5 _database_code_depnum_ccdc_archive 'CCDC 826237' #TrackingRef '- all(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; PC-7-3-Iacac 2-(4-iodophenyl)-2,4-pentanedione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 I O2' _chemical_formula_sum 'C11 H11 I O2' _chemical_formula_weight 302.10 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 21.0708(12) _cell_length_b 6.9034(4) _cell_length_c 7.3624(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1070.94(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9926 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 33.71 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.874 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 2.961 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4910 _exptl_absorpt_correction_T_max 0.7176 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28491 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 33.73 _reflns_number_total 2293 _reflns_number_gt 2112 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0200P)^2^+0.4500P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2293 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0209 _refine_ls_R_factor_gt 0.0186 _refine_ls_wR_factor_ref 0.0478 _refine_ls_wR_factor_gt 0.0467 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.003 _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 I1 I 0.448932(5) 0.2500 0.126393(15) 0.02357(4) Uani 1 2 d S . . C11 C 0.64514(8) 0.2500 0.9099(2) 0.0228(3) Uani 1 2 d S . . H11A H 0.6492 0.1475 1.0013 0.034 Uiso 0.50 1 calc PR . . H11B H 0.6072 0.2267 0.8360 0.034 Uiso 0.50 1 calc PR . . H11C H 0.6414 0.3758 0.9707 0.034 Uiso 0.50 1 calc PR . . C12 C 0.70239(7) 0.2500 0.7908(2) 0.0182(3) Uani 1 2 d S . . O12 O 0.75677(7) 0.2500 0.88120(16) 0.0238(3) Uani 1 2 d S . . H12 H 0.7871(13) 0.2500 0.793(4) 0.029 Uiso 1 2 d S . . C13 C 0.70127(7) 0.2500 0.6030(2) 0.0168(3) Uani 1 2 d S . . C14 C 0.76064(7) 0.2500 0.5070(2) 0.0193(3) Uani 1 2 d S . . O14 O 0.81340(6) 0.2500 0.58904(18) 0.0268(3) Uani 1 2 d S . . C15 C 0.76097(8) 0.2500 0.3035(2) 0.0233(3) Uani 1 2 d S . . H15A H 0.7319 0.3499 0.2588 0.035 Uiso 0.50 1 calc PR . . H15B H 0.7473 0.1229 0.2590 0.035 Uiso 0.50 1 calc PR . . H15C H 0.8040 0.2772 0.2597 0.035 Uiso 0.50 1 calc PR . . C21 C 0.64092(7) 0.2500 0.4986(2) 0.0163(2) Uani 1 2 d S . . C22 C 0.61245(5) 0.07648(17) 0.44586(16) 0.0204(2) Uani 1 1 d . . . H22 H 0.6309 -0.0429 0.4824 0.024 Uiso 1 1 calc R . . C23 C 0.55756(5) 0.0750(2) 0.34072(18) 0.0214(2) Uani 1 1 d . . . H23 H 0.5386 -0.0441 0.3055 0.026 Uiso 1 1 calc R . . C24 C 0.53078(7) 0.2500 0.2879(2) 0.0182(3) Uani 1 2 d S . . 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 I1 0.01562(6) 0.03478(7) 0.02030(6) 0.000 -0.00472(3) 0.000 C11 0.0189(7) 0.0332(9) 0.0162(6) 0.000 0.0025(5) 0.000 C12 0.0179(6) 0.0221(7) 0.0147(6) 0.000 -0.0014(5) 0.000 O12 0.0188(6) 0.0379(7) 0.0147(5) 0.000 -0.0037(4) 0.000 C13 0.0145(6) 0.0227(7) 0.0131(6) 0.000 -0.0004(4) 0.000 C14 0.0155(6) 0.0268(8) 0.0155(6) 0.000 -0.0002(5) 0.000 O14 0.0148(5) 0.0461(8) 0.0194(5) 0.000 -0.0011(4) 0.000 C15 0.0215(7) 0.0340(9) 0.0145(6) 0.000 0.0017(5) 0.000 C21 0.0136(6) 0.0213(7) 0.0140(6) 0.000 -0.0003(4) 0.000 C22 0.0186(4) 0.0205(5) 0.0220(5) 0.0007(4) -0.0040(4) 0.0007(4) C23 0.0192(5) 0.0223(5) 0.0227(5) -0.0022(4) -0.0038(4) -0.0019(4) C24 0.0123(6) 0.0264(7) 0.0158(6) 0.000 -0.0011(5) 0.000 _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 I1 C24 2.0949(15) . ? C11 C12 1.491(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O12 1.325(2) . ? C12 C13 1.383(2) . ? O12 H12 0.91(3) . ? C13 C14 1.437(2) . ? C13 C21 1.486(2) . ? C14 O14 1.265(2) . ? C14 C15 1.498(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C21 C22 1.3950(14) . ? C21 C22 1.3950(14) 7_565 ? C22 C23 1.3917(16) . ? C22 H22 0.9500 . ? C23 C24 1.3886(15) . ? C23 H23 0.9500 . ? C24 C23 1.3886(15) 7_565 ? 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 C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O12 C12 C13 121.12(15) . . ? O12 C12 C11 113.86(14) . . ? C13 C12 C11 125.03(15) . . ? C12 O12 H12 104.3(16) . . ? C12 C13 C14 118.49(14) . . ? C12 C13 C21 122.13(14) . . ? C14 C13 C21 119.38(13) . . ? O14 C14 C13 122.03(14) . . ? O14 C14 C15 118.24(15) . . ? C13 C14 C15 119.73(14) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C22 C21 C22 118.34(14) . 7_565 ? C22 C21 C13 120.81(7) . . ? C22 C21 C13 120.81(7) 7_565 . ? C23 C22 C21 121.23(11) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 119.16(12) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C23 120.87(15) 7_565 . ? C23 C24 I1 119.57(7) 7_565 . ? C23 C24 I1 119.57(7) . . ? 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 O12 C12 C13 C14 0.0 . . . . ? C11 C12 C13 C14 180.0 . . . . ? O12 C12 C13 C21 180.0 . . . . ? C11 C12 C13 C21 0.0 . . . . ? C12 C13 C14 O14 0.0 . . . . ? C21 C13 C14 O14 180.0 . . . . ? C12 C13 C14 C15 180.0 . . . . ? C21 C13 C14 C15 0.0 . . . . ? C12 C13 C21 C22 -91.06(12) . . . . ? C14 C13 C21 C22 88.94(12) . . . . ? C12 C13 C21 C22 91.06(12) . . . 7_565 ? C14 C13 C21 C22 -88.94(12) . . . 7_565 ? C22 C21 C22 C23 1.0(2) 7_565 . . . ? C13 C21 C22 C23 -176.92(13) . . . . ? C21 C22 C23 C24 -0.1(2) . . . . ? C22 C23 C24 C23 -0.9(2) . . . 7_565 ? C22 C23 C24 I1 179.09(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H12 O14 0.91(3) 1.60(3) 2.4598(18) 156(3) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 33.73 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.464 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.078 #END data_2Cu _database_code_depnum_ccdc_archive 'CCDC 826238' #TrackingRef '- all(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AS-12 2-(4-tolyl)-2,4-pentanedione, copper(II) tetrafluoroborate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H13 O2)2 Cu ; _chemical_formula_sum 'C24 H26 Cu O4' _chemical_formula_weight 441.99 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 11.9427(6) _cell_length_b 16.3128(8) _cell_length_c 21.4984(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4188.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9976 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 35.41 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1848 _exptl_absorpt_coefficient_mu 1.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6698 _exptl_absorpt_correction_T_max 0.7471 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19756 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 34.97 _reflns_number_total 2238 _reflns_number_gt 2034 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0500P)^2^+4.0000P] 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 2238 _refine_ls_number_parameters 70 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _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 Cu1 Cu 0.1250 0.1250 0.1250 0.01543(8) Uani 1 4 d S . . C11 C 0.33239(8) 0.09820(7) 0.28164(4) 0.02252(18) Uani 1 1 d . . . H11A H 0.3941 0.0868 0.2529 0.034 Uiso 1 1 calc R . . H11B H 0.3217 0.0512 0.3094 0.034 Uiso 1 1 calc R . . H11C H 0.3502 0.1470 0.3063 0.034 Uiso 1 1 calc R . . C12 C 0.22668(8) 0.11298(6) 0.24524(4) 0.01706(15) Uani 1 1 d . . . O12 O 0.23902(6) 0.11345(5) 0.18615(3) 0.01928(14) Uani 1 1 d . . . C13 C 0.1250 0.1250 0.27703(6) 0.0169(2) Uani 1 2 d S . . C21 C 0.1250 0.1250 0.34668(6) 0.0173(2) Uani 1 2 d S . . C22 C 0.11960(9) 0.05168(7) 0.37994(5) 0.02097(18) Uani 1 1 d . . . H22 H 0.1105 -0.0003 0.3583 0.025 Uiso 1 1 d R . . C23 C 0.11947(8) 0.05187(7) 0.44459(5) 0.02312(19) Uani 1 1 d . . . H23 H 0.1106 -0.0008 0.4655 0.028 Uiso 1 1 d R . . C24 C 0.1250 0.1250 0.47795(7) 0.0220(3) Uani 1 2 d S . . C31 C 0.1250 0.1250 0.54789(7) 0.0324(4) Uani 1 2 d S . . H31A H 0.1291 0.1816 0.5631 0.049 Uiso 0.50 1 calc PR . . H31B H 0.1899 0.0941 0.5631 0.049 Uiso 0.50 1 calc PR . . H31C H 0.0560 0.0993 0.5631 0.049 Uiso 0.50 1 calc PR . . 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 Cu1 0.01608(11) 0.02038(12) 0.00983(11) 0.000 0.000 0.000 C11 0.0184(4) 0.0325(5) 0.0168(4) 0.0021(3) -0.0027(3) 0.0000(3) C12 0.0173(4) 0.0215(4) 0.0124(3) 0.0004(3) -0.0009(3) -0.0015(3) O12 0.0176(3) 0.0289(3) 0.0114(3) 0.0006(2) 0.0001(2) 0.0005(2) C13 0.0182(5) 0.0216(5) 0.0110(5) 0.000 0.000 -0.0002(4) C21 0.0184(5) 0.0221(5) 0.0114(5) 0.000 0.000 0.0009(4) C22 0.0264(4) 0.0216(4) 0.0149(4) 0.0008(3) 0.0007(3) 0.0012(3) C23 0.0260(4) 0.0284(5) 0.0149(4) 0.0047(3) 0.0012(3) 0.0028(3) C24 0.0189(5) 0.0348(7) 0.0122(5) 0.000 0.000 0.0033(4) C31 0.0318(8) 0.0537(11) 0.0117(6) 0.000 0.000 0.0027(6) _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 Cu1 O12 1.9021(7) 11_454 ? Cu1 O12 1.9021(7) . ? Cu1 O12 1.9021(7) 8_544 ? Cu1 O12 1.9021(7) 14_445 ? C11 C12 1.5047(13) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O12 1.2789(11) . ? C12 C13 1.4071(11) . ? C13 C12 1.4071(11) 14_445 ? C13 C21 1.4975(18) . ? C21 C22 1.3950(12) 14_445 ? C21 C22 1.3950(12) . ? C22 C23 1.3898(14) . ? C22 H22 0.9740 . ? C23 C24 1.3935(14) . ? C23 H23 0.9749 . ? C24 C23 1.3935(14) 14_445 ? C24 C31 1.504(2) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? 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 O12 Cu1 O12 168.63(4) 11_454 . ? O12 Cu1 O12 92.56(4) 11_454 8_544 ? O12 Cu1 O12 88.56(4) . 8_544 ? O12 Cu1 O12 88.56(4) 11_454 14_445 ? O12 Cu1 O12 92.56(4) . 14_445 ? O12 Cu1 O12 168.63(4) 8_544 14_445 ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O12 C12 C13 125.52(9) . . ? O12 C12 C11 114.89(8) . . ? C13 C12 C11 119.59(9) . . ? C12 O12 Cu1 127.20(6) . . ? C12 C13 C12 121.89(12) 14_445 . ? C12 C13 C21 119.05(6) 14_445 . ? C12 C13 C21 119.05(6) . . ? C22 C21 C22 118.32(13) 14_445 . ? C22 C21 C13 120.84(6) 14_445 . ? C22 C21 C13 120.84(6) . . ? C23 C22 C21 120.71(10) . . ? C23 C22 H22 118.7 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 121.10(10) . . ? C22 C23 H23 117.3 . . ? C24 C23 H23 121.5 . . ? C23 C24 C23 118.05(13) . 14_445 ? C23 C24 C31 120.97(7) . . ? C23 C24 C31 120.97(7) 14_445 . ? C24 C31 H31A 109.5 . . ? C24 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C24 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? 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 C13 C12 O12 Cu1 -3.24(13) . . . . ? C11 C12 O12 Cu1 176.87(6) . . . . ? O12 Cu1 O12 C12 -93.89(8) 11_454 . . . ? O12 Cu1 O12 C12 170.25(10) 8_544 . . . ? O12 Cu1 O12 C12 1.57(6) 14_445 . . . ? O12 C12 C13 C12 1.72(7) . . . 14_445 ? C11 C12 C13 C12 -178.40(9) . . . 14_445 ? O12 C12 C13 C21 -178.28(7) . . . . ? C11 C12 C13 C21 1.60(9) . . . . ? C12 C13 C21 C22 -83.91(6) 14_445 . . 14_445 ? C12 C13 C21 C22 96.09(6) . . . 14_445 ? C12 C13 C21 C22 96.09(6) 14_445 . . . ? C12 C13 C21 C22 -83.91(6) . . . . ? C22 C21 C22 C23 0.08(7) 14_445 . . . ? C13 C21 C22 C23 -179.92(7) . . . . ? C21 C22 C23 C24 -0.17(14) . . . . ? C22 C23 C24 C23 0.08(7) . . . 14_445 ? C22 C23 C24 C31 -179.92(7) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.499 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.081 #END data_3Cu _database_code_depnum_ccdc_archive 'CCDC 826239' #TrackingRef '- all(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; D1 bis[2-(4-chlorophenyl)-2,4-pentanedionato]copper(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H10 Cl O2)2 Cu ; _chemical_formula_sum 'C22 H20 Cl2 Cu O4' _chemical_formula_weight 482.82 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 11.9763(7) _cell_length_b 15.8265(9) _cell_length_c 21.7849(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4129.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9944 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 33.85 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1976 _exptl_absorpt_coefficient_mu 1.343 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6196 _exptl_absorpt_correction_T_max 0.7467 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19816 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 33.14 _reflns_number_total 1979 _reflns_number_gt 1794 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0500P)^2^+2.5000P] 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 1979 _refine_ls_number_parameters 70 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 Cu1 Cu 0.1250 0.1250 0.1250 0.01613(9) Uani 1 4 d S . . Cl1 Cl 0.1250 0.1250 0.550886(17) 0.03715(13) Uani 1 2 d S . . C11 C 0.33257(8) 0.10213(7) 0.27994(4) 0.02299(19) Uani 1 1 d . . . H11A H 0.3943 0.0900 0.2517 0.034 Uiso 1 1 calc R . . H11B H 0.3230 0.0547 0.3083 0.034 Uiso 1 1 calc R . . H11C H 0.3493 0.1535 0.3032 0.034 Uiso 1 1 calc R . . C12 C 0.22667(8) 0.11472(6) 0.24380(4) 0.01771(17) Uani 1 1 d . . . O12 O 0.23908(6) 0.11510(5) 0.18545(3) 0.02038(15) Uani 1 1 d . . . C13 C 0.1250 0.1250 0.27503(6) 0.0174(2) Uani 1 2 d S . . C21 C 0.1250 0.1250 0.34361(6) 0.0177(2) Uani 1 2 d S . . C22 C 0.11052(10) 0.04990(7) 0.37625(4) 0.02201(19) Uani 1 1 d . . . H22 H 0.1014 -0.0021 0.3546 0.026 Uiso 1 1 d R . . C23 C 0.11014(9) 0.04952(8) 0.44005(5) 0.0248(2) Uani 1 1 d . . . H23 H 0.1013 -0.0031 0.4609 0.030 Uiso 1 1 d R . . C24 C 0.1250 0.1250 0.47099(6) 0.0227(3) Uani 1 2 d S . . 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 Cu1 0.01605(13) 0.02170(14) 0.01064(12) 0.000 0.000 0.000 Cl1 0.0334(2) 0.0665(3) 0.01148(18) 0.000 0.000 -0.00027(17) C11 0.0185(4) 0.0331(5) 0.0174(4) 0.0021(3) -0.0026(3) -0.0006(4) C12 0.0179(4) 0.0213(4) 0.0140(4) 0.0005(3) -0.0011(3) -0.0020(3) O12 0.0173(3) 0.0313(4) 0.0125(3) 0.0010(2) 0.0000(2) 0.0001(2) C13 0.0176(6) 0.0225(6) 0.0121(5) 0.000 0.000 -0.0008(4) C21 0.0189(6) 0.0228(6) 0.0115(5) 0.000 0.000 0.0012(4) C22 0.0278(5) 0.0216(4) 0.0167(4) 0.0008(3) 0.0018(3) -0.0001(4) C23 0.0275(5) 0.0301(5) 0.0168(4) 0.0057(3) 0.0019(3) 0.0023(4) C24 0.0188(6) 0.0378(8) 0.0116(5) 0.000 0.000 0.0041(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 Cu1 O12 1.9041(7) 11_454 ? Cu1 O12 1.9041(7) . ? Cu1 O12 1.9041(7) 8_544 ? Cu1 O12 1.9041(7) 14_445 ? Cl1 C24 1.7406(14) . ? C11 C12 1.5060(14) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O12 1.2797(11) . ? C12 C13 1.4043(12) . ? C13 C12 1.4043(12) 14_445 ? C13 C21 1.4942(18) . ? C21 C22 1.3957(12) 14_445 ? C21 C22 1.3957(12) . ? C22 C23 1.3899(15) . ? C22 H22 0.9551 . ? C23 C24 1.3831(14) . ? C23 H23 0.9554 . ? C24 C23 1.3831(14) 14_445 ? 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 O12 Cu1 O12 170.56(4) 11_454 . ? O12 Cu1 O12 92.48(4) 11_454 8_544 ? O12 Cu1 O12 88.30(4) . 8_544 ? O12 Cu1 O12 88.30(4) 11_454 14_445 ? O12 Cu1 O12 92.48(4) . 14_445 ? O12 Cu1 O12 170.56(4) 8_544 14_445 ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O12 C12 C13 125.54(10) . . ? O12 C12 C11 114.97(9) . . ? C13 C12 C11 119.49(9) . . ? C12 O12 Cu1 127.16(7) . . ? C12 C13 C12 122.04(12) 14_445 . ? C12 C13 C21 118.98(6) 14_445 . ? C12 C13 C21 118.98(6) . . ? C22 C21 C22 118.76(12) 14_445 . ? C22 C21 C13 120.62(6) 14_445 . ? C22 C21 C13 120.62(6) . . ? C23 C22 C21 120.89(10) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 118.89(10) . . ? C24 C23 H23 122.4 . . ? C22 C23 H23 118.7 . . ? C23 C24 C23 121.67(13) . 14_445 ? C23 C24 Cl1 119.16(6) . . ? C23 C24 Cl1 119.16(6) 14_445 . ? 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 C13 C12 O12 Cu1 -2.66(13) . . . . ? C11 C12 O12 Cu1 177.46(7) . . . . ? O12 Cu1 O12 C12 1.29(6) 14_445 . . . ? O12 C12 C13 C12 1.41(7) . . . 14_445 ? C11 C12 C13 C12 -178.71(9) . . . 14_445 ? O12 C12 C13 C21 -178.59(7) . . . . ? C11 C12 C13 C21 1.29(9) . . . . ? C12 C13 C21 C22 -90.69(7) 14_445 . . 14_445 ? C12 C13 C21 C22 89.31(7) . . . 14_445 ? C12 C13 C21 C22 89.31(7) 14_445 . . . ? C12 C13 C21 C22 -90.69(7) . . . . ? C22 C21 C22 C23 0.17(8) 14_445 . . . ? C13 C21 C22 C23 -179.83(8) . . . . ? C21 C22 C23 C24 -0.34(15) . . . . ? C22 C23 C24 C23 0.17(7) . . . 14_445 ? C22 C23 C24 Cl1 -179.83(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.461 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.069 #END data_4Cu _database_code_depnum_ccdc_archive 'CCDC 826240' #TrackingRef '- all(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AS-6 bis[2-(4-bromophenyl)-2,4-pentanedionato]copper(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H10 Br O2)2 (Cu) ; _chemical_formula_sum 'C22 H20 Br2 Cu O4' _chemical_formula_weight 571.74 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 12.0389(11) _cell_length_b 15.8409(12) _cell_length_c 22.1627(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4226.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2565 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 33.24 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2264 _exptl_absorpt_coefficient_mu 4.841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3443 _exptl_absorpt_correction_T_max 0.5506 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9902 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 33.47 _reflns_number_total 2055 _reflns_number_gt 1497 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^+6.0000P] 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 2055 _refine_ls_number_parameters 70 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _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 Cu1 Cu 0.1250 0.1250 0.1250 0.01521(10) Uani 1 4 d S . . Br1 Br 0.1250 0.1250 0.550302(11) 0.03342(10) Uani 1 2 d S . . C11 C 0.33144(15) 0.10409(11) 0.27730(8) 0.0214(3) Uani 1 1 d . . . H11A H 0.3924 0.0899 0.2498 0.032 Uiso 1 1 calc R . . H11B H 0.3215 0.0584 0.3066 0.032 Uiso 1 1 calc R . . H11C H 0.3491 0.1566 0.2987 0.032 Uiso 1 1 calc R . . O12 O 0.23812(10) 0.11571(7) 0.18449(5) 0.0188(2) Uani 1 1 d . . . C12 C 0.22595(14) 0.11560(10) 0.24169(7) 0.0165(3) Uani 1 1 d . . . C13 C 0.1250 0.1250 0.27259(10) 0.0154(4) Uani 1 2 d S . . C21 C 0.1250 0.1250 0.33983(9) 0.0154(4) Uani 1 2 d S . . C22 C 0.11202(15) 0.04982(10) 0.37185(8) 0.0201(3) Uani 1 1 d . . . H22 H 0.1029 -0.0022 0.3502 0.024 Uiso 1 1 d R . . C23 C 0.11180(15) 0.04961(11) 0.43456(8) 0.0221(3) Uani 1 1 d . . . H23 H 0.1030 -0.0030 0.4555 0.027 Uiso 1 1 d R . . C24 C 0.1250 0.1250 0.46443(10) 0.0199(4) Uani 1 2 d S . . 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 Cu1 0.01532(19) 0.02256(19) 0.00776(16) 0.000 0.000 0.000 Br1 0.02898(17) 0.0627(2) 0.00859(12) 0.000 0.000 -0.00087(13) C11 0.0176(8) 0.0307(9) 0.0158(7) 0.0021(6) -0.0019(6) 0.0003(6) O12 0.0164(6) 0.0307(6) 0.0093(5) 0.0013(4) 0.0007(4) -0.0008(5) C12 0.0191(8) 0.0198(7) 0.0105(6) 0.0007(5) -0.0011(5) -0.0016(6) C13 0.0156(10) 0.0199(9) 0.0107(9) 0.000 0.000 -0.0012(8) C21 0.0148(10) 0.0205(9) 0.0109(9) 0.000 0.000 0.0008(9) C22 0.0251(8) 0.0215(7) 0.0139(7) -0.0001(6) 0.0011(6) -0.0003(6) C23 0.0253(9) 0.0274(8) 0.0138(7) 0.0059(6) 0.0008(6) 0.0008(7) C24 0.0154(11) 0.0356(12) 0.0086(9) 0.000 0.000 0.0020(9) _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 Cu1 O12 1.9011(12) 11_454 ? Cu1 O12 1.9011(12) . ? Cu1 O12 1.9011(12) 8_544 ? Cu1 O12 1.9011(12) 14_445 ? Br1 C24 1.903(2) . ? C11 C12 1.506(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O12 C12 1.2763(19) . ? C12 C13 1.403(2) . ? C13 C12 1.403(2) 14_445 ? C13 C21 1.490(3) . ? C21 C22 1.395(2) 14_445 ? C21 C22 1.395(2) . ? C22 C23 1.390(2) . ? C22 H22 0.9599 . ? C23 C24 1.375(2) . ? C23 H23 0.9599 . ? C24 C23 1.375(2) 14_445 ? 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 O12 Cu1 O12 171.12(7) 11_454 . ? O12 Cu1 O12 92.19(7) 11_454 8_544 ? O12 Cu1 O12 88.50(7) . 8_544 ? O12 Cu1 O12 88.50(7) 11_454 14_445 ? O12 Cu1 O12 92.19(7) . 14_445 ? O12 Cu1 O12 171.12(7) 8_544 14_445 ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 O12 Cu1 127.36(11) . . ? O12 C12 C13 125.75(16) . . ? O12 C12 C11 115.08(15) . . ? C13 C12 C11 119.18(15) . . ? C12 C13 C12 121.6(2) 14_445 . ? C12 C13 C21 119.22(10) 14_445 . ? C12 C13 C21 119.22(10) . . ? C22 C21 C22 118.8(2) 14_445 . ? C22 C21 C13 120.58(10) 14_445 . ? C22 C21 C13 120.58(10) . . ? C23 C22 C21 120.73(15) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 118.63(16) . . ? C24 C23 H23 122.4 . . ? C22 C23 H23 119.0 . . ? C23 C24 C23 122.4(2) . 14_445 ? C23 C24 Br1 118.78(11) . . ? C23 C24 Br1 118.78(11) 14_445 . ? 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 O12 Cu1 O12 C12 172.12(16) 8_544 . . . ? O12 Cu1 O12 C12 0.98(11) 14_445 . . . ? Cu1 O12 C12 C13 -2.0(2) . . . . ? Cu1 O12 C12 C11 177.89(10) . . . . ? O12 C12 C13 C12 1.08(12) . . . 14_445 ? C11 C12 C13 C12 -178.84(16) . . . 14_445 ? O12 C12 C13 C21 -178.92(12) . . . . ? C11 C12 C13 C21 1.16(16) . . . . ? C12 C13 C21 C22 -90.49(11) 14_445 . . 14_445 ? C12 C13 C21 C22 89.51(11) . . . 14_445 ? C12 C13 C21 C22 89.51(11) 14_445 . . . ? C12 C13 C21 C22 -90.49(11) . . . . ? C22 C21 C22 C23 0.11(13) 14_445 . . . ? C13 C21 C22 C23 -179.89(13) . . . . ? C21 C22 C23 C24 -0.2(3) . . . . ? C22 C23 C24 C23 0.10(13) . . . 14_445 ? C22 C23 C24 Br1 -179.90(13) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 33.47 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.459 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.090 #END data_5Cu _database_code_depnum_ccdc_archive 'CCDC 826241' #TrackingRef '- all(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AS-10 2-(4-iodophenyl)-2,4-pentanedione, copper(II) nitrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C11 H10 I O2)2 Cu ; _chemical_formula_sum 'C22 H20 Cu I2 O4' _chemical_formula_weight 665.72 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2510(4) _cell_length_b 7.7262(4) _cell_length_c 17.8085(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.525(3) _cell_angle_gamma 90.00 _cell_volume 1112.38(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4770 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 33.69 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.988 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 3.782 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4397 _exptl_absorpt_correction_T_max 0.6195 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13650 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 33.72 _reflns_number_total 4394 _reflns_number_gt 3699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^+0.7000P] 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 4394 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 Cu1 Cu 0.5000 0.5000 0.5000 0.01683(8) Uani 1 2 d S . . I1 I -0.20855(2) 1.01709(3) 0.805684(9) 0.02953(7) Uani 1 1 d . . . C11 C 0.3895(3) 0.9751(3) 0.59128(17) 0.0276(5) Uani 1 1 d . . . H11A H 0.4352 1.0397 0.5529 0.041 Uiso 1 1 calc R . . H11B H 0.4662 0.9817 0.6409 0.041 Uiso 1 1 calc R . . H11C H 0.2828 1.0252 0.5959 0.041 Uiso 1 1 calc R . . C12 C 0.3657(3) 0.7890(3) 0.56698(12) 0.0194(4) Uani 1 1 d . . . O12 O 0.4640(2) 0.7344(2) 0.52546(9) 0.0226(3) Uani 1 1 d . . . C13 C 0.2428(2) 0.6876(3) 0.59098(11) 0.0175(4) Uani 1 1 d . . . C14 C 0.2170(3) 0.5136(3) 0.57020(12) 0.0177(4) Uani 1 1 d . . . O14 O 0.30390(19) 0.4240(2) 0.53238(9) 0.0196(3) Uani 1 1 d . . . C15 C 0.0760(3) 0.4147(4) 0.59343(13) 0.0226(4) Uani 1 1 d . . . H15A H 0.0688 0.2988 0.5706 0.034 Uiso 1 1 calc R . . H15B H -0.0281 0.4767 0.5753 0.034 Uiso 1 1 calc R . . H15C H 0.0961 0.4048 0.6494 0.034 Uiso 1 1 calc R . . C21 C 0.1360(2) 0.7688(3) 0.64037(11) 0.0167(4) Uani 1 1 d . . . C22 C 0.1742(3) 0.7436(3) 0.71955(11) 0.0172(4) Uani 1 1 d . . . H22 H 0.2678 0.6758 0.7416 0.021 Uiso 1 1 calc R . . C23 C 0.0766(2) 0.8167(3) 0.76667(11) 0.0175(4) Uani 1 1 d . . . H23 H 0.1025 0.7979 0.8205 0.021 Uiso 1 1 calc R . . C24 C -0.0582(2) 0.9167(3) 0.73437(12) 0.0185(4) Uani 1 1 d . . . C25 C -0.0988(3) 0.9444(4) 0.65604(13) 0.0238(4) Uani 1 1 d . . . H25 H -0.1916 1.0134 0.6343 0.029 Uiso 1 1 calc R . . C26 C -0.0010(3) 0.8689(4) 0.60977(12) 0.0239(5) Uani 1 1 d . . . H26 H -0.0287 0.8863 0.5559 0.029 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 Cu1 0.01939(17) 0.01651(19) 0.01755(17) -0.00030(12) 0.01083(13) 0.00166(12) I1 0.02531(9) 0.03997(12) 0.02643(9) -0.00427(6) 0.01264(6) 0.01253(6) C11 0.0311(12) 0.0206(12) 0.0368(13) -0.0052(9) 0.0208(10) -0.0020(9) C12 0.0225(9) 0.0183(10) 0.0204(9) 0.0010(7) 0.0110(7) 0.0023(8) O12 0.0282(8) 0.0183(8) 0.0271(8) -0.0011(6) 0.0194(7) 0.0016(6) C13 0.0175(8) 0.0195(10) 0.0171(8) -0.0007(7) 0.0076(7) 0.0024(7) C14 0.0159(8) 0.0234(11) 0.0148(8) -0.0004(7) 0.0055(7) 0.0027(7) O14 0.0208(7) 0.0201(8) 0.0208(7) -0.0034(6) 0.0107(6) 0.0008(6) C15 0.0186(9) 0.0275(13) 0.0237(10) -0.0033(8) 0.0095(8) -0.0039(8) C21 0.0173(8) 0.0171(10) 0.0175(8) -0.0008(7) 0.0077(7) 0.0013(7) C22 0.0166(8) 0.0185(10) 0.0175(8) -0.0015(7) 0.0055(7) 0.0022(7) C23 0.0187(9) 0.0189(10) 0.0159(8) -0.0008(7) 0.0059(7) 0.0012(7) C24 0.0162(8) 0.0206(11) 0.0215(9) -0.0013(7) 0.0103(7) 0.0019(7) C25 0.0205(10) 0.0296(13) 0.0226(10) 0.0028(9) 0.0072(8) 0.0097(9) C26 0.0229(10) 0.0322(13) 0.0179(9) 0.0040(8) 0.0069(7) 0.0085(9) _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 Cu1 O12 1.9048(17) 3_666 ? Cu1 O12 1.9048(17) . ? Cu1 O14 1.9153(15) 3_666 ? Cu1 O14 1.9153(15) . ? I1 C24 2.0935(18) . ? C11 C12 1.503(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O12 1.274(2) . ? C12 C13 1.413(3) . ? C13 C14 1.399(3) . ? C13 C21 1.501(3) . ? C14 O14 1.281(2) . ? C14 C15 1.517(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C21 C26 1.388(3) . ? C21 C22 1.396(3) . ? C22 C23 1.393(3) . ? C22 H22 0.9500 . ? C23 C24 1.382(3) . ? C23 H23 0.9500 . ? C24 C25 1.384(3) . ? C25 C26 1.391(3) . ? C25 H25 0.9500 . ? C26 H26 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 O12 Cu1 O12 180.00(9) 3_666 . ? O12 Cu1 O14 92.21(7) 3_666 3_666 ? O12 Cu1 O14 87.79(7) . 3_666 ? O12 Cu1 O14 87.79(7) 3_666 . ? O12 Cu1 O14 92.21(7) . . ? O14 Cu1 O14 180.0 3_666 . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O12 C12 C13 124.8(2) . . ? O12 C12 C11 114.96(19) . . ? C13 C12 C11 120.28(18) . . ? C12 O12 Cu1 126.94(15) . . ? C14 C13 C12 122.24(18) . . ? C14 C13 C21 118.72(18) . . ? C12 C13 C21 119.0(2) . . ? O14 C14 C13 125.94(19) . . ? O14 C14 C15 114.3(2) . . ? C13 C14 C15 119.76(18) . . ? C14 O14 Cu1 125.99(15) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C26 C21 C22 118.44(17) . . ? C26 C21 C13 122.03(18) . . ? C22 C21 C13 119.53(18) . . ? C23 C22 C21 120.71(19) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C22 119.33(18) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 121.22(18) . . ? C23 C24 I1 118.67(14) . . ? C25 C24 I1 120.04(16) . . ? C24 C25 C26 118.7(2) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? C21 C26 C25 121.6(2) . . ? C21 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? 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 C13 C12 O12 Cu1 -11.9(3) . . . . ? C11 C12 O12 Cu1 167.25(18) . . . . ? O14 Cu1 O12 C12 -164.8(2) 3_666 . . . ? O14 Cu1 O12 C12 15.2(2) . . . . ? O12 C12 C13 C14 -0.4(4) . . . . ? C11 C12 C13 C14 -179.5(2) . . . . ? O12 C12 C13 C21 179.6(2) . . . . ? C11 C12 C13 C21 0.5(3) . . . . ? C12 C13 C14 O14 4.5(4) . . . . ? C21 C13 C14 O14 -175.6(2) . . . . ? C12 C13 C14 C15 -176.0(2) . . . . ? C21 C13 C14 C15 3.9(3) . . . . ? C13 C14 O14 Cu1 4.2(3) . . . . ? C15 C14 O14 Cu1 -175.30(14) . . . . ? O12 Cu1 O14 C14 168.59(18) 3_666 . . . ? O12 Cu1 O14 C14 -11.41(18) . . . . ? C14 C13 C21 C26 -98.3(3) . . . . ? C12 C13 C21 C26 81.6(3) . . . . ? C14 C13 C21 C22 81.5(3) . . . . ? C12 C13 C21 C22 -98.6(3) . . . . ? C26 C21 C22 C23 0.2(3) . . . . ? C13 C21 C22 C23 -179.6(2) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? C22 C23 C24 C25 0.6(4) . . . . ? C22 C23 C24 I1 177.59(16) . . . . ? C23 C24 C25 C26 0.1(4) . . . . ? I1 C24 C25 C26 -176.90(19) . . . . ? C22 C21 C26 C25 0.5(4) . . . . ? C13 C21 C26 C25 -179.7(2) . . . . ? C24 C25 C26 C21 -0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 33.72 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.918 _refine_diff_density_min -0.907 _refine_diff_density_rms 0.137 #END