#------------------------------------------------------------------------------ #$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/00/16/4001619.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4001619 loop_ _publ_author_name 'Polyakov, Alexey O.' 'Arkenbout, Anne H.' 'Baas, Jacob' 'Blake, Graeme R.' 'Meetsma, Auke' 'Caretta, Antonio' 'van Loosdrecht, Paul H. M.' 'Palstra, Thomas T. M.' _publ_section_related_literature ; ; _publ_section_title ; Coexisting Ferromagnetic and Ferroelectric Order in a CuCl4-based Organic--Inorganic Hybrid ; _journal_issue 1 _journal_name_full 'Chemistry of Materials' _journal_page_first 133 _journal_paper_doi 10.1021/cm2023696 _journal_volume 24 _journal_year 2012 _chemical_compound_source 'see text' _chemical_formula_moiety '2(C8 H12 N), Cl4 Cu' _chemical_formula_sum 'C16 H24 Cl4 Cu N2' _chemical_formula_weight 449.72 _chemical_name_systematic ? _space_group_IT_number 64 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 64 _symmetry_space_group_name_Hall '-C 2ac 2' _symmetry_space_group_name_H-M 'C m c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary heavy _atom_sites_solution_secondary direct _audit_creation_date '2009-09-21 13:30:04' _audit_creation_method ; PLATON option (version :: 60709) SHELXL97-2 & Manual Editing ; _audit_update_record ; ? ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 39.021(8) _cell_length_b 7.3430(15) _cell_length_c 7.3939(15) _cell_measurement_reflns_used 2107 _cell_measurement_temperature 373(1) _cell_measurement_theta_max 23.02 _cell_measurement_theta_min 3.13 _cell_volume 2118.6(7) _computing_cell_refinement 'SAINT-Plus (Bruker, 2007)' _computing_data_collection 'SMART (Bruker, 2007)' _computing_data_reduction SAINT-Plus _computing_molecular_graphics ; PLATON (Spek, 2003) PLUTO (Meetsma, 2009) ; _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution ; DIRDIF-08 (Beurskens et al., 2008) ; _diffrn_ambient_temperature 373(1) _diffrn_detector_area_resol_mean 66.06 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type ; Bruker Smart Apex; CCD area detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_detector ; CCD area-detector ; _diffrn_radiation_monochromator 'parallel mounted graphite' _diffrn_radiation_source 'fine focus sealed Siemens Mo tube ' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_max 49 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 7895 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, decay and absorption and reduced to F~o~^2^ using SAINT-Plus & SADABS (Bruker, 2007). ; _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 26.72 _diffrn_reflns_theta_min 3.13 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.535 _exptl_absorpt_correction_T_max 0.8577 _exptl_absorpt_correction_T_min 0.7256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS, (Bruker, 2007))' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 924 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.756 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.104 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 68 _refine_ls_number_reflns 1146 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.128 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0544 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1044P)^2^+0.6794P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1481 _refine_ls_wR_factor_ref 0.1597 _reflns_number_gt 913 _reflns_number_total 1146 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cm2023696_si_001.cif _cod_data_source_block global _cod_original_sg_symbol_Hall '-C 2bc 2' _cod_database_code 4001619 #BEGIN Tags that were not found in dictionaries: _vrn_publ_code_void_volume 128.1 _vrn_publ_code_number_frames 1800 _vrn_publ_code_frame_time_sec 10.0 _vrn_publ_code_meas_time_hour 7.8 #END Tags that were not found in dictionaries loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2-y,1/2+z 3 x,-y,-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 x,1/2+y,1/2-z 7 -x,y,z 8 x,1/2-y,1/2+z 9 1/2+x,1/2+y,z 10 1/2-x,-y,1/2+z 11 1/2+x,1/2-y,-z 12 1/2-x,y,1/2-z 13 1/2-x,1/2-y,-z 14 1/2+x,y,1/2-z 15 1/2-x,1/2+y,z 16 1/2+x,-y,1/2+z 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 N1 0.070(4) 0.078(4) 0.082(4) -0.004(3) 0.036(8) -0.017(10) C1 0.080(7) 0.163(13) 0.24(2) 0.074(10) 0.085(15) 0.043(15) C2 0.152(15) 0.232(18) 0.17(2) -0.088(16) -0.050(14) 0.061(14) C3 0.050(5) 0.262(19) 0.29(2) 0.134(14) 0.00 0.0000 C4 0.133(8) 0.260(14) 0.237(13) 0.153(13) 0.014(6) 0.003(7) C5 0.097(7) 0.202(12) 0.250(13) 0.033(11) 0.038(7) -0.025(6) C6 0.081(8) 0.22(2) 0.24(2) -0.036(12) 0.00 0.0000 Cu1 0.0626(6) 0.0447(5) 0.0412(5) -0.0076(3) 0.00 0.0000 Cl1 0.0604(9) 0.0866(11) 0.0822(11) 0.0013(6) 0.00 0.0000 Cl2 0.1076(10) 0.0485(6) 0.0451(7) -0.0088(5) 0.00 0.0000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv N1 N Uani 0.05465(14) 0.500 0.00000 1.000 0.077(2) C1 C Uani 0.0895(3) 0.500 0.00000 1.000 0.161(8) C2 C Uani 0.1196(2) 0.455(2) -0.1085(16) 0.5 0.185(10) C3 C Uani 0.1505(3) 0.500 0.00000 1.000 0.201(9) C4 C Uani 0.1699(2) 0.6185(16) -0.1079(16) 1.0 0.210(7) C5 C Uani 0.2045(2) 0.6148(16) -0.0941(17) 1.0 0.183(6) C6 C Uani 0.2197(4) 0.500 0.00000 1.000 0.180(10) Cu1 Cu Uani 0.000 0.50000 0.50000 1.000 0.0495(3) Cl1 Cl Uani -0.05866(4) 0.500 0.50000 1.000 0.0764(6) Cl2 Cl Uani 0.000 0.27901(16) 0.28124(16) 1.000 0.0671(5) H1 H Uiso 0.09425 0.43231 0.10982 0.5 0.1945 H1' H Uiso 0.09425 0.62571 0.03151 0.5 0.1945 H2 H Uiso 0.11946 0.52552 -0.21974 0.5 0.2200 H2' H Uiso 0.11946 0.32705 -0.13938 0.5 0.2200 H4 H Uiso 0.15919 0.69821 -0.18753 1.0 0.2522 H5 H Uiso 0.21733 0.70086 -0.15703 1.0 0.2197 H6 H Uiso 0.24355 0.500 0.00000 1.000 0.2171 H9 H Uiso 0.04704 0.54756 0.10319 0.5 0.1152 H9' H Uiso 0.04704 0.38624 -0.01069 0.5 0.1152 H9" H Uiso 0.04704 0.56620 -0.09250 0.5 0.1152 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cl1 Cu1 Cl2 90 . . yes Cl1 Cu1 Cl2 90 . 2_555 yes Cl1 Cu1 Cl2 90 . 3_566 yes Cl1 Cu1 Cl2 90 . 4_555 yes Cl1 Cu1 Cl1 180 . 5_566 yes Cl2 Cu1 Cl2 90.33(4) . 2_555 yes Cl2 Cu1 Cl2 180 . 3_566 yes Cl2 Cu1 Cl2 89.67(4) . 4_555 yes Cl1 Cu1 Cl2 90 5_566 . yes Cl2 Cu1 Cl2 89.67(4) 2_555 3_566 yes Cl2 Cu1 Cl2 180 2_555 4_555 yes Cl1 Cu1 Cl2 90 5_566 2_555 yes Cl2 Cu1 Cl2 90.33(4) 3_566 4_555 yes Cl1 Cu1 Cl2 90 5_566 3_566 yes Cl1 Cu1 Cl2 90 5_566 4_555 yes Cu1 Cl2 Cu1 179.48(5) . 2_554 yes C1 N1 H9 109 . 3_565 no C1 N1 H9' 109 . 3_565 no C1 N1 H9" 109 . 3_565 no H9 N1 H9' 109 . . no H9 N1 H9" 109 . . no H9 N1 H9 141 . 3_565 no H9 N1 H9' 56 . 3_565 no H9 N1 H9" 56 . 3_565 no H9' N1 H9" 109 . . no H9 N1 H9' 56 3_565 . no H9' N1 H9' 141 . 3_565 no H9' N1 H9" 56 . 3_565 no H9 N1 H9" 56 3_565 . no H9' N1 H9" 56 3_565 . no H9" N1 H9" 141 . 3_565 no H9 N1 H9' 109 3_565 3_565 no H9 N1 H9" 109 3_565 3_565 no H9' N1 H9" 109 3_565 3_565 no C1 N1 H9" 109 . . no C1 N1 H9 109 . . no C1 N1 H9' 109 . . no C2 C1 C2 72.9(8) . 3_565 no N1 C1 C2 143.6(5) . 3_565 yes N1 C1 C2 143.6(5) . . yes C1 C2 C3 107.8(9) . . no C2 C3 C2 71.5(8) . 3_565 no C2 C3 C4 105.6(7) . . no C2 C3 C4 127.4(7) 3_565 . no C4 C3 C4 114.7(10) . 3_565 no C2 C3 C4 127.4(8) . 3_565 no C2 C3 C4 105.6(7) 3_565 3_565 no C3 C4 C5 118.9(10) . . no C4 C5 C6 122.1(12) . . no C5 C6 C5 123.0(14) . 3_565 no C2 C1 H1' 101 3_565 3_565 no H1 C1 H1' 104 3_565 3_565 no N1 C1 H1 101 . 3_565 no N1 C1 H1' 101 . 3_565 no C2 C1 H1 101 . . no C2 C1 H1' 101 . . no C2 C1 H1 60 . 3_565 no C2 C1 H1' 60 . 3_565 no H1 C1 H1' 104 . . no C2 C1 H1 60 3_565 . no H1 C1 H1 158 . 3_565 no H1 C1 H1' 71 . 3_565 no C2 C1 H1' 60 3_565 . no H1' C1 H1' 158 . 3_565 no C2 C1 H1 101 3_565 3_565 no N1 C1 H1 101 . . no N1 C1 H1' 101 . . no H1 C1 H1' 71 3_565 . no C1 C2 H2 110 . . no C3 C2 H2 110 . . no C3 C2 H2' 110 . . no C1 C2 H2' 110 . . no H2 C2 H2' 109 . . no C5 C4 H4 121 . . no C3 C4 H4 121 . . no C4 C5 H5 119 . . no C6 C5 H5 119 . . no C5 C6 H6 118 . . no C5 C6 H6 118 3_565 . no 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 Cl2 2.9192(13) 2_555 yes Cu1 Cl1 2.2890(16) . yes Cu1 Cl2 2.2912(13) . yes Cu1 Cl1 2.2890(16) 5_566 yes Cu1 Cl2 2.2912(13) 3_566 yes Cu1 Cl2 2.9192(13) 4_555 yes N1 C1 1.360(13) . yes N1 H9" 0.89 3_565 no N1 H9" 0.89 . no N1 H9 0.89 . no N1 H9' 0.89 . no N1 H9 0.89 3_565 no N1 H9' 0.89 3_565 no C1 C2 1.460(13) . no C1 C2 1.460(13) 3_565 no C2 C3 1.486(13) . no C3 C4 1.402(12) . no C3 C4 1.402(12) 3_565 no C4 C5 1.354(11) . no C5 C6 1.244(14) . no C1 H1' 0.97 . no C1 H1 0.97 . no C1 H1 0.97 3_565 no C1 H1' 0.97 3_565 no C2 H2 0.97 . no C2 H2' 0.97 . no C4 H4 0.93 . no C5 H5 0.93 . no C6 H6 0.93 . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl1 Cl2 3.2387(15) . no Cl1 Cl2 3.2387(15) 3_566 no Cl1 Cl2 3.2387(15) 3_566 no Cl2 N1 3.371(4) 2_555 no Cl2 N1 3.371(4) 4_545 no Cl2 N1 3.392(4) . no Cl2 N1 3.392(4) . no Cl2 N1 3.392(4) 5_565 no Cl2 Cl1 3.2387(15) . no Cl2 Cl1 3.2387(15) 5_566 no Cl2 N1 3.392(4) 7_555 no Cl2 Cl1 3.2387(15) 5_566 no Cl1 H9" 3.09 5_565 no Cl1 H9' 2.87 4_555 no Cl1 H1' 3.09 4_545 no Cl1 H9" 3.09 7_556 no Cl1 H9 2.99 5_566 no Cl1 H1' 3.09 2_565 no Cl1 H9 2.99 7_555 no Cl1 H9' 2.87 2_555 no Cl2 H9 2.64 4_545 no Cl2 H9' 2.94 . no Cl2 H9' 2.68 2_555 no Cl2 H9" 2.57 5_565 no Cl2 H9 3.00 . no Cl2 H9' 2.94 7_555 no Cl2 H9 3.00 7_555 no Cl2 H9" 2.57 3_565 no N1 Cl2 3.392(4) 3_565 no N1 Cl2 3.371(4) 2_554 no N1 Cl2 3.392(4) . no N1 Cl2 3.371(4) 2_554 no N1 Cl2 3.392(4) 5_565 no N1 Cl2 3.371(4) 4_555 no N1 Cl2 3.371(4) 4_555 no N1 Cl2 3.392(4) . no C2 H4 2.87 6_544 no C4 H1 2.98 3_565 no H1 C4 2.98 3_565 no H1' Cl1 3.09 2_564 no H1' Cl1 3.09 4_555 no H2 H4 2.02 . no H2' H4 2.22 6_544 no H4 C2 2.87 6_554 no H4 H2' 2.22 6_554 no H4 H2 2.02 . no H9 Cl1 2.99 5_566 no H9 Cl2 3.00 . no H9 Cl1 2.99 5_566 no H9 Cl2 3.00 . no H9 Cl2 2.64 4_555 no H9 Cl2 2.64 4_555 no H9' Cl2 2.94 . no H9' Cl2 2.68 2_554 no H9' Cl2 2.68 2_554 no H9' Cl1 2.87 2_554 no H9' Cl1 2.87 2_554 no H9' Cl2 2.94 . no H9" Cl2 2.57 5_565 no H9" Cl1 3.09 7_554 no H9" Cl1 3.09 5_565 no H9" Cl2 2.57 3_565 no 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 _geom_hbond_publ_flag N1 H9 Cl2 0.8900 2.6400 3.371(4) 140 4_555 yes N1 H9' Cl2 0.8900 2.6800 3.371(4) 135 2_554 yes N1 H9" Cl2 0.8900 2.5700 3.392(4) 154 3_565 yes 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_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 179.98(3) . . . no C2 C1 C2 C3 0.0(8) 3_565 . . no C2 C1 C2 C3 0.0(8) . 3_565 . no C1 C2 C3 C4 -124.9(9) . . . no C1 C2 C3 C2 0.0(8) . . 3_565 no C1 C2 C3 C4 95.8(11) . . 3_565 no C2 C3 C4 C5 -148.0(11) . . . no C2 C3 C4 C5 133.6(11) 3_565 . . no C4 C3 C4 C5 -2.8(13) 3_565 . . no C3 C4 C5 C6 5.9(17) . . . no C4 C5 C6 C5 -3.1(16) . . 3_565 no