# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_CuF2(H2O)2(3ClPy)10K _database_code_depnum_ccdc_archive 'CCDC 905521' #TrackingRef 'CuF2(H2O)2(3-ClPy)_10K_Rev.cif' #=========================================================================== # # The submitted manuscript has been created by UChicago Argonne, LLC, # Operator of Argonne National Laboratory ("Argonne"). Argonne, a U.S. # Department of Energy Office of Science laboratory, is operated under # Contract No. DE-AC02-06CH11357. The U.S. Government retains for itself, # and others acting on its behalf, a paid-up nonexclusive, irrevocable # worldwide license in said article to reproduce, prepare derivative works, # distribute copies to the public, and perform publicly and display # publicly, by or on behalf of the Government. #=========================================================================== _audit_creation_method 'manual editing of SHELXL-97 cif file' _chemical_name_systematic ; ? ; _chemical_name_common 'Copper(ii) difluoride dihydrate 3-chloropyridine' _chemical_melting_point ? _chemical_formula_moiety 'Cu 2+, 2(F 1-), C5 H4 Cl N, 2(H2 O)' _chemical_formula_sum 'C5 H8 Cl Cu F2 N O2' _chemical_formula_weight 251.11 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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 monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.7471(13) _cell_length_b 7.6434(15) _cell_length_c 16.409(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.649(3) _cell_angle_gamma 90.00 _cell_volume 845.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 10(2) _cell_measurement_reflns_used 4822 _cell_measurement_theta_min 2.941 _cell_measurement_theta_max 31.437 _exptl_crystal_description rod _exptl_crystal_colour blue _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.973 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 2.890 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.501 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'TWINABS, Bruker AXS V2008/2' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.000 cm. ; _diffrn_radiation_probe x-ray _diffrn_ambient_temperature 10(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker APEX II' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '3-circle goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 2743 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 31.44 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 31.44 _diffrn_measured_fraction_theta_full 0.985 _reflns_number_total 2811 _reflns_number_gt 2562 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.1a (Crystal Impact, 2005)' _computing_publication_material 'SHELXTL (Bruker, 2006)' _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. Hydrogen atoms were located in the difference maps, but the following instructions were used in the SHELXL refinement in order to restrain the water bond lengths and angles to reasonable values. This was necessary because of low scattering factor of hydrogen. DFIX 0.82 0.03 O1 H1A DFIX 0.82 0.03 O1 H1B DANG 1.30 0.06 H1A H1B DFIX 0.82 0.03 O2 H2A DFIX 0.82 0.03 O2 H2B DANG 1.30 0.06 H2A H2B ; _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^)+(0.1476P)^2^+0.2945P] 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 2811 _refine_ls_number_parameters 122 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1968 _refine_ls_wR_factor_gt 0.1578 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.163 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 2.323 _refine_diff_density_min -2.078 _refine_diff_density_rms 0.439 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 0.23535(7) 0.91610(6) 0.20263(2) 0.00401(18) Uani 1 1 d . . . F1 F 0.2329(3) 1.1633(3) 0.20135(12) 0.0074(5) Uani 1 1 d . . . F2 F 0.2372(3) 0.6696(3) 0.20901(13) 0.0073(5) Uani 1 1 d . . . O1 O 0.0302(4) 0.9169(4) 0.2893(2) 0.0060(5) Uani 1 1 d D . . H1A H -0.033(7) 0.826(4) 0.289(4) 0.007 Uiso 1 1 d D . . H1B H -0.042(7) 0.995(5) 0.299(4) 0.007 Uiso 1 1 d D . . O2 O 0.4895(4) 0.9160(4) 0.2835(2) 0.0086(6) Uani 1 1 d D . . H2A H 0.551(8) 0.823(4) 0.292(4) 0.010 Uiso 1 1 d D . . H2B H 0.563(7) 0.999(5) 0.285(4) 0.010 Uiso 1 1 d D . . N1 N 0.2519(5) 0.9097(4) 0.07801(19) 0.0056(6) Uani 1 1 d . . . C2 C 0.2469(6) 1.0589(5) 0.0346(2) 0.0057(6) Uani 1 1 d . . . H2 H 0.2410 1.1677 0.0624 0.007 Uiso 1 1 calc R . . C3 C 0.2503(6) 1.0577(5) -0.0499(2) 0.0054(6) Uani 1 1 d . . . Cl1 Cl 0.24103(13) 1.25460(11) -0.10255(5) 0.0074(2) Uani 1 1 d . . . C4 C 0.2600(6) 0.9005(5) -0.0925(2) 0.0069(7) Uani 1 1 d . . . H4 H 0.2640 0.8983 -0.1503 0.008 Uiso 1 1 calc R . . C5 C 0.2637(6) 0.7457(4) -0.0469(2) 0.0069(7) Uani 1 1 d . . . H5 H 0.2681 0.6354 -0.0734 0.008 Uiso 1 1 calc R . . C6 C 0.2609(5) 0.7553(5) 0.0379(2) 0.0072(6) Uani 1 1 d . . . H6 H 0.2654 0.6499 0.0686 0.009 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 0.0074(3) 0.0017(3) 0.0030(3) 0.00006(12) 0.00035(18) -0.00013(14) F1 0.0116(11) 0.0035(10) 0.0069(10) -0.0008(7) 0.0001(9) 0.0011(8) F2 0.0114(11) 0.0046(10) 0.0058(9) 0.0003(7) -0.0004(9) 0.0011(8) O1 0.0088(13) 0.0019(13) 0.0076(13) 0.0007(10) 0.0028(9) -0.0004(10) O2 0.0080(13) 0.0058(14) 0.0118(15) 0.0017(11) -0.0022(10) -0.0006(10) N1 0.0062(14) 0.0055(13) 0.0051(13) -0.0003(9) 0.0004(10) -0.0008(11) C2 0.0096(16) 0.0039(13) 0.0036(13) -0.0002(11) 0.0004(11) 0.0010(12) C3 0.0079(16) 0.0026(12) 0.0055(14) 0.0002(11) -0.0013(13) 0.0014(11) Cl1 0.0107(4) 0.0062(4) 0.0052(4) 0.0026(3) -0.0001(3) 0.0010(3) C4 0.0104(16) 0.0045(15) 0.0058(15) -0.0016(11) 0.0008(12) -0.0012(13) C5 0.0100(16) 0.0053(15) 0.0055(15) -0.0026(13) 0.0019(13) -0.0025(14) C6 0.0108(17) 0.0041(14) 0.0067(14) 0.0021(11) -0.0005(12) -0.0012(14) _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 F2 1.887(2) . ? Cu1 F1 1.890(2) . ? Cu1 O1 2.030(3) . ? Cu1 N1 2.054(3) . ? Cu1 O2 2.119(3) . ? O1 H1A 0.81(3) . ? O1 H1B 0.79(3) . ? O2 H2A 0.83(3) . ? O2 H2B 0.80(3) . ? N1 C2 1.345(4) . ? N1 C6 1.353(4) . ? C2 C3 1.388(5) . ? C2 H2 0.9500 . ? C3 C4 1.393(5) . ? C3 Cl1 1.735(4) . ? C4 C5 1.399(5) . ? C4 H4 0.9500 . ? C5 C6 1.395(5) . ? C5 H5 0.9500 . ? C6 H6 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 F2 Cu1 F1 177.45(9) . . ? F2 Cu1 O1 88.13(11) . . ? F1 Cu1 O1 89.92(11) . . ? F2 Cu1 N1 91.77(10) . . ? F1 Cu1 N1 90.78(10) . . ? O1 Cu1 N1 140.18(13) . . ? F2 Cu1 O2 87.80(11) . . ? F1 Cu1 O2 90.80(11) . . ? O1 Cu1 O2 96.83(12) . . ? N1 Cu1 O2 122.97(13) . . ? Cu1 O1 H1A 111(4) . . ? Cu1 O1 H1B 126(4) . . ? H1A O1 H1B 109(5) . . ? Cu1 O2 H2A 119(4) . . ? Cu1 O2 H2B 120(4) . . ? H2A O2 H2B 111(5) . . ? C2 N1 C6 118.9(3) . . ? C2 N1 Cu1 120.4(2) . . ? C6 N1 Cu1 120.7(2) . . ? N1 C2 C3 121.5(3) . . ? N1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 Cl1 119.3(3) . . ? C4 C3 Cl1 120.0(3) . . ? C3 C4 C5 117.5(3) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N1 C6 C5 122.2(3) . . ? N1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? 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 F2 Cu1 N1 C2 177.0(3) . . . . ? F1 Cu1 N1 C2 -3.0(3) . . . . ? O1 Cu1 N1 C2 87.8(3) . . . . ? O2 Cu1 N1 C2 -94.5(3) . . . . ? F2 Cu1 N1 C6 -0.7(3) . . . . ? F1 Cu1 N1 C6 179.3(3) . . . . ? O1 Cu1 N1 C6 -89.9(3) . . . . ? O2 Cu1 N1 C6 87.9(3) . . . . ? C6 N1 C2 C3 0.2(6) . . . . ? Cu1 N1 C2 C3 -177.5(3) . . . . ? N1 C2 C3 C4 -0.3(6) . . . . ? N1 C2 C3 Cl1 179.3(3) . . . . ? C2 C3 C4 C5 0.8(6) . . . . ? Cl1 C3 C4 C5 -178.9(3) . . . . ? C3 C4 C5 C6 -1.0(5) . . . . ? C2 N1 C6 C5 -0.5(5) . . . . ? Cu1 N1 C6 C5 177.2(3) . . . . ? C4 C5 C6 N1 0.9(6) . . . . ? data_CuF2(H2O)2(3ClPy)100K _database_code_depnum_ccdc_archive 'CCDC 905522' #TrackingRef 'CuF2(H2O)2(3-ClPy)_100K_Rev.cif' #=========================================================================== # # The submitted manuscript has been created by UChicago Argonne, LLC, # Operator of Argonne National Laboratory ("Argonne"). Argonne, a U.S. # Department of Energy Office of Science laboratory, is operated under # Contract No. DE-AC02-06CH11357. The U.S. Government retains for itself, # and others acting on its behalf, a paid-up nonexclusive, irrevocable # worldwide license in said article to reproduce, prepare derivative works, # distribute copies to the public, and perform publicly and display # publicly, by or on behalf of the Government. #=========================================================================== _audit_creation_method 'manual editing of SHELXL-97 cif file' _chemical_name_systematic ; ? ; _chemical_name_common 'Copper(ii) difluoride dihydrate 3-chloropyridine' _chemical_melting_point ? _chemical_formula_moiety 'Cu 2+, 2(F 1-), C5 H4 Cl N, 2(H2 O)' _chemical_formula_sum 'C5 H8 Cl Cu F2 N O2' _chemical_formula_weight 251.11 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.76700(10) _cell_length_b 7.6416(2) _cell_length_c 16.4281(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.7230(10) _cell_angle_gamma 90.00 _cell_volume 849.12(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7556 _cell_measurement_theta_min 2.940 _cell_measurement_theta_max 31.498 _exptl_crystal_description rod _exptl_crystal_colour blue _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.964 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 2.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.575 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'TWINABS, Bruker AXS V2008/2' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.000 cm. ; _diffrn_radiation_probe x-ray _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker APEX II' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '3-circle goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 2755 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0110 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 31.50 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 0.982 _reflns_number_total 2825 _reflns_number_gt 2743 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.1a (Crystal Impact, 2005)' _computing_publication_material 'SHELXTL (Bruker, 2006)' _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. Hydrogen atoms were located in the difference maps, but the following instructions were used in the SHELXL refinement in order to restrain the water bond lengths and angles to reasonable values. This was necessary because of low scattering factor of hydrogen. DFIX 0.82 0.03 O1 H1A DFIX 0.82 0.03 O1 H1B DANG 1.30 0.06 H1A H1B DFIX 0.82 0.03 O2 H2A DFIX 0.82 0.03 O2 H2B DANG 1.30 0.06 H2A H2B ; _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^)+(0.0305P)^2^+0.3435P] 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 2825 _refine_ls_number_parameters 122 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0215 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0586 _refine_ls_wR_factor_gt 0.0580 _refine_ls_goodness_of_fit_ref 1.209 _refine_ls_restrained_S_all 1.212 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.566 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.196 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 0.24059(3) 0.91609(2) 0.202860(9) 0.00907(5) Uani 1 1 d . . . F1 F 0.23898(16) 1.16274(11) 0.20188(5) 0.01293(19) Uani 1 1 d . . . F2 F 0.24167(15) 0.66948(11) 0.20890(5) 0.01157(18) Uani 1 1 d . . . O1 O 0.02552(16) 0.91768(18) 0.28781(8) 0.0124(2) Uani 1 1 d D . . H1A H -0.043(3) 0.839(3) 0.2820(17) 0.015 Uiso 1 1 d D . . H1B H -0.030(4) 1.002(3) 0.2936(16) 0.015 Uiso 1 1 d D . . O2 O 0.48757(16) 0.91628(19) 0.28448(9) 0.0140(2) Uani 1 1 d D . . H2A H 0.553(3) 0.830(3) 0.2943(17) 0.017 Uiso 1 1 d D . . H2B H 0.554(3) 0.990(3) 0.2811(17) 0.017 Uiso 1 1 d D . . N1 N 0.25115(19) 0.90988(15) 0.07798(7) 0.01095(19) Uani 1 1 d . . . C2 C 0.2478(2) 1.05957(18) 0.03482(8) 0.0116(2) Uani 1 1 d . . . H2 H 0.2440 1.1683 0.0627 0.014 Uiso 1 1 calc R . . C3 C 0.2498(2) 1.05845(19) -0.04967(8) 0.0127(3) Uani 1 1 d . . . Cl1 Cl 0.24435(7) 1.25559(5) -0.10185(2) 0.01781(8) Uani 1 1 d . . . C4 C 0.2554(2) 0.9021(2) -0.09203(9) 0.0163(3) Uani 1 1 d . . . H4 H 0.2566 0.9000 -0.1498 0.020 Uiso 1 1 calc R . . C5 C 0.2593(3) 0.74757(19) -0.04677(8) 0.0171(3) Uani 1 1 d . . . H5 H 0.2638 0.6374 -0.0734 0.020 Uiso 1 1 calc R . . C6 C 0.2566(3) 0.75642(18) 0.03757(8) 0.0142(3) Uani 1 1 d . . . H6 H 0.2587 0.6506 0.0679 0.017 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 0.01340(8) 0.00506(8) 0.00878(8) 0.00013(5) 0.00071(6) 0.00004(7) F1 0.0191(5) 0.0061(3) 0.0136(4) -0.0010(3) 0.0013(4) 0.0003(4) F2 0.0148(5) 0.0061(3) 0.0138(4) 0.0008(3) 0.0005(4) 0.0000(3) O1 0.0122(4) 0.0084(5) 0.0168(6) 0.0002(5) 0.0038(4) 0.0006(5) O2 0.0122(5) 0.0089(6) 0.0206(6) 0.0006(5) -0.0034(4) -0.0010(5) N1 0.0131(5) 0.0095(5) 0.0102(5) -0.0001(4) 0.0005(4) -0.0005(5) C2 0.0134(6) 0.0104(5) 0.0109(5) 0.0003(4) 0.0000(5) 0.0003(5) C3 0.0136(6) 0.0129(5) 0.0116(6) 0.0032(4) -0.0002(5) -0.0004(6) Cl1 0.02240(19) 0.01706(15) 0.01392(15) 0.00705(11) -0.00016(14) 0.00004(17) C4 0.0189(8) 0.0186(6) 0.0114(6) -0.0013(5) 0.0004(5) -0.0006(8) C5 0.0247(8) 0.0139(6) 0.0127(6) -0.0034(5) 0.0020(7) -0.0007(8) C6 0.0198(7) 0.0101(5) 0.0127(5) -0.0006(4) 0.0008(6) -0.0004(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 F1 1.8849(8) . ? Cu1 F2 1.8871(8) . ? Cu1 O1 2.0465(12) . ? Cu1 N1 2.0554(11) . ? Cu1 O2 2.1110(12) . ? O1 H1A 0.76(2) . ? O1 H1B 0.75(2) . ? O2 H2A 0.81(2) . ? O2 H2B 0.72(2) . ? N1 C2 1.3457(17) . ? N1 C6 1.3486(17) . ? C2 C3 1.3885(18) . ? C2 H2 0.9500 . ? C3 C4 1.384(2) . ? C3 Cl1 1.7331(14) . ? C4 C5 1.395(2) . ? C4 H4 0.9500 . ? C5 C6 1.3879(19) . ? C5 H5 0.9500 . ? C6 H6 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 F1 Cu1 F2 177.47(3) . . ? F1 Cu1 O1 89.76(5) . . ? F2 Cu1 O1 88.38(5) . . ? F1 Cu1 N1 90.85(4) . . ? F2 Cu1 N1 91.68(4) . . ? O1 Cu1 N1 136.68(5) . . ? F1 Cu1 O2 90.52(5) . . ? F2 Cu1 O2 88.03(5) . . ? O1 Cu1 O2 97.62(4) . . ? N1 Cu1 O2 125.68(5) . . ? Cu1 O1 H1A 110(2) . . ? Cu1 O1 H1B 117(2) . . ? H1A O1 H1B 113(3) . . ? Cu1 O2 H2A 123.1(18) . . ? Cu1 O2 H2B 116(2) . . ? H2A O2 H2B 108(2) . . ? C2 N1 C6 118.69(12) . . ? C2 N1 Cu1 120.38(9) . . ? C6 N1 Cu1 120.91(9) . . ? N1 C2 C3 121.40(13) . . ? N1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 120.62(13) . . ? C4 C3 Cl1 120.15(11) . . ? C2 C3 Cl1 119.23(11) . . ? C3 C4 C5 117.59(13) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? C6 C5 C4 119.36(13) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? N1 C6 C5 122.35(13) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? 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 F1 Cu1 N1 C2 -1.99(12) . . . . ? F2 Cu1 N1 C2 177.99(12) . . . . ? O1 Cu1 N1 C2 88.57(13) . . . . ? O2 Cu1 N1 C2 -93.24(13) . . . . ? F1 Cu1 N1 C6 179.66(13) . . . . ? F2 Cu1 N1 C6 -0.36(13) . . . . ? O1 Cu1 N1 C6 -89.79(14) . . . . ? O2 Cu1 N1 C6 88.41(14) . . . . ? C6 N1 C2 C3 0.0(2) . . . . ? Cu1 N1 C2 C3 -178.36(12) . . . . ? N1 C2 C3 C4 0.0(3) . . . . ? N1 C2 C3 Cl1 179.77(12) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? Cl1 C3 C4 C5 -179.91(14) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C2 N1 C6 C5 0.1(2) . . . . ? Cu1 N1 C6 C5 178.51(13) . . . . ? C4 C5 C6 N1 -0.3(3) . . . . ? data_CuF2(H2O)2(3ClPy)200K _database_code_depnum_ccdc_archive 'CCDC 905523' #TrackingRef 'CuF2(H2O)2(3-ClPy)_200K_Rev.cif' #=========================================================================== # # The submitted manuscript has been created by UChicago Argonne, LLC, # Operator of Argonne National Laboratory ("Argonne"). Argonne, a U.S. # Department of Energy Office of Science laboratory, is operated under # Contract No. DE-AC02-06CH11357. The U.S. Government retains for itself, # and others acting on its behalf, a paid-up nonexclusive, irrevocable # worldwide license in said article to reproduce, prepare derivative works, # distribute copies to the public, and perform publicly and display # publicly, by or on behalf of the Government. #=========================================================================== _audit_creation_method 'manual editing of SHELXL-97 cif file' _chemical_name_systematic ; ? ; _chemical_name_common 'Copper(ii) difluoride dihydrate 3-chloropyridine' _chemical_melting_point ? _chemical_formula_moiety 'Cu 2+, 2(F 1-), C5 H4 Cl N, 2(H2 O)' _chemical_formula_sum 'C5 H8 Cl Cu F2 N O2' _chemical_formula_weight 251.11 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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 Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_Int_Tables_number 62 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 16.4782(3) _cell_length_b 6.81060(10) _cell_length_c 7.6385(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 857.24(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 7530 _cell_measurement_theta_min 2.940 _cell_measurement_theta_max 31.554 _exptl_crystal_description rod _exptl_crystal_colour blue _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.946 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 2.850 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5572 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.000 cm. ; _diffrn_radiation_probe x-ray _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker APEX II' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '3-circle goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 11200 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _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 2.94 _diffrn_reflns_theta_max 31.57 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 31.57 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 1531 _reflns_number_gt 1468 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.1a (Crystal Impact, 2005)' _computing_publication_material 'SHELXTL (Bruker, 2006)' _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. Hydrogen atoms were located in the difference maps, but the following instructions were used in the SHELXL refinement in order to restrain the water bond lengths and angles to reasonable values. This was necessary because of low scattering factor of hydrogen. DFIX 0.82 0.03 O1 H1A DFIX 0.82 0.03 O1 H1B DANG 1.30 0.06 H1A H1B ; _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^)+(0.0289P)^2^+0.2658P] 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 SHELXL _refine_ls_extinction_coef 0.0074(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1531 _refine_ls_number_parameters 77 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0212 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0550 _refine_ls_wR_factor_gt 0.0543 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.611 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.217 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 0.203442(10) 0.7500 0.41551(2) 0.01743(7) Uani 1 2 d S . . F1 F 0.20291(5) 0.7500 0.66208(12) 0.02331(19) Uani 1 2 d S . . F2 F 0.20921(5) 0.7500 0.16917(12) 0.02152(18) Uani 1 2 d S . . O1 O 0.28548(6) 0.98177(13) 0.41632(10) 0.02427(17) Uani 1 1 d D . . H1A H 0.2860(9) 1.047(2) 0.336(2) 0.029 Uiso 1 1 d D . . H1B H 0.2868(9) 1.042(3) 0.494(2) 0.029 Uiso 1 1 d D . . N1 N 0.07855(8) 0.7500 0.40977(15) 0.0197(2) Uani 1 2 d S . . C2 C 0.03566(9) 0.7500 0.55992(19) 0.0210(3) Uani 1 2 d S . . H2 H 0.0637 0.7500 0.6686 0.025 Uiso 1 2 calc SR . . C3 C -0.04855(10) 0.7500 0.5591(2) 0.0238(3) Uani 1 2 d S . . Cl1 Cl -0.10017(3) 0.7500 0.75681(6) 0.03559(11) Uani 1 2 d S . . C4 C -0.09085(10) 0.7500 0.4036(2) 0.0306(3) Uani 1 2 d S . . H4 H -0.1485 0.7500 0.4019 0.037 Uiso 1 2 calc SR . . C5 C -0.04621(10) 0.7500 0.2493(2) 0.0330(4) Uani 1 2 d S . . H5 H -0.0731 0.7500 0.1392 0.040 Uiso 1 2 calc SR . . C6 C 0.03781(10) 0.7500 0.2570(2) 0.0261(3) Uani 1 2 d S . . H6 H 0.0677 0.7500 0.1507 0.031 Uiso 1 2 calc SR . . 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 0.01757(10) 0.02510(11) 0.00961(10) 0.000 0.00025(5) 0.000 F1 0.0254(4) 0.0336(5) 0.0109(4) 0.000 -0.0016(3) 0.000 F2 0.0262(4) 0.0280(4) 0.0104(4) 0.000 0.0013(3) 0.000 O1 0.0357(4) 0.0219(4) 0.0152(3) -0.0009(3) 0.0005(3) -0.0073(3) N1 0.0185(5) 0.0248(6) 0.0157(5) 0.000 0.0001(4) 0.000 C2 0.0187(6) 0.0261(6) 0.0182(6) 0.000 0.0011(5) 0.000 C3 0.0193(6) 0.0255(7) 0.0267(7) 0.000 0.0049(5) 0.000 Cl1 0.0278(2) 0.0452(2) 0.0338(2) 0.000 0.01421(16) 0.000 C4 0.0182(6) 0.0382(9) 0.0354(9) 0.000 -0.0023(6) 0.000 C5 0.0226(7) 0.0497(10) 0.0268(8) 0.000 -0.0074(6) 0.000 C6 0.0218(6) 0.0383(8) 0.0181(6) 0.000 -0.0023(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 Cu1 F1 1.8834(9) . ? Cu1 F2 1.8841(9) . ? Cu1 N1 2.0585(13) . ? Cu1 O1 2.0783(9) 7_575 ? Cu1 O1 2.0783(9) . ? O1 H1A 0.757(16) . ? O1 H1B 0.720(16) . ? N1 C6 1.3460(18) . ? N1 C2 1.3472(18) . ? C2 C3 1.388(2) . ? C2 H2 0.9500 . ? C3 C4 1.377(2) . ? C3 Cl1 1.7332(16) . ? C4 C5 1.390(2) . ? C4 H4 0.9500 . ? C5 C6 1.386(2) . ? C5 H5 0.9500 . ? C6 H6 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 F1 Cu1 F2 177.38(4) . . ? F1 Cu1 N1 90.95(4) . . ? F2 Cu1 N1 91.67(4) . . ? F1 Cu1 O1 90.00(3) . 7_575 ? F2 Cu1 O1 88.29(3) . 7_575 ? N1 Cu1 O1 130.57(3) . 7_575 ? F1 Cu1 O1 90.00(3) . . ? F2 Cu1 O1 88.29(3) . . ? N1 Cu1 O1 130.57(3) . . ? O1 Cu1 O1 98.84(5) 7_575 . ? Cu1 O1 H1A 117.0(12) . . ? Cu1 O1 H1B 117.0(13) . . ? H1A O1 H1B 109(2) . . ? C6 N1 C2 118.45(14) . . ? C6 N1 Cu1 121.13(10) . . ? C2 N1 Cu1 120.42(10) . . ? N1 C2 C3 121.38(14) . . ? N1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 120.66(15) . . ? C4 C3 Cl1 120.20(13) . . ? C2 C3 Cl1 119.13(13) . . ? C3 C4 C5 117.63(15) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? C6 C5 C4 119.51(15) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? N1 C6 C5 122.37(15) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? 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 F1 Cu1 N1 C6 180.0 . . . . ? F2 Cu1 N1 C6 0.0 . . . . ? O1 Cu1 N1 C6 -89.18(4) 7_575 . . . ? O1 Cu1 N1 C6 89.18(4) . . . . ? F1 Cu1 N1 C2 0.0 . . . . ? F2 Cu1 N1 C2 180.0 . . . . ? O1 Cu1 N1 C2 90.82(4) 7_575 . . . ? O1 Cu1 N1 C2 -90.82(4) . . . . ? C6 N1 C2 C3 0.0 . . . . ? Cu1 N1 C2 C3 180.0 . . . . ? N1 C2 C3 C4 0.0 . . . . ? N1 C2 C3 Cl1 180.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? Cl1 C3 C4 C5 180.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C2 N1 C6 C5 0.0 . . . . ? Cu1 N1 C6 C5 180.0 . . . . ? C4 C5 C6 N1 0.0 . . . . ? data_CuF2(H2O)2(3ClPy)RT _database_code_depnum_ccdc_archive 'CCDC 905524' #TrackingRef 'CuF2(H2O)2(3ClPy)_RT_Rev.cif' #=========================================================================== # # The submitted manuscript has been created by UChicago Argonne, LLC, # Operator of Argonne National Laboratory ("Argonne"). Argonne, a U.S. # Department of Energy Office of Science laboratory, is operated under # Contract No. DE-AC02-06CH11357. The U.S. Government retains for itself, # and others acting on its behalf, a paid-up nonexclusive, irrevocable # worldwide license in said article to reproduce, prepare derivative works, # distribute copies to the public, and perform publicly and display # publicly, by or on behalf of the Government. #=========================================================================== _audit_creation_method 'manual editing of SHELXL-97 cif file' _chemical_name_systematic ; ? ; _chemical_name_common 'Copper(ii) difluoride dihydrate 3-chloropyridine' _chemical_melting_point ? _chemical_formula_moiety 'Cu 2+, 2(F 1-), C5 H4 Cl N, 2(H2 O)' _chemical_formula_sum 'C5 H8 Cl Cu F2 N O2' _chemical_formula_weight 251.11 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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 Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_Int_Tables_number 62 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 16.5192(3) _cell_length_b 6.86930(10) _cell_length_c 7.62880(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 865.68(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8379 _cell_measurement_theta_min 2.466 _cell_measurement_theta_max 31.575 _exptl_crystal_description rod _exptl_crystal_colour blue _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.927 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 2.822 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5886 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.000 cm. ; _diffrn_radiation_probe x-ray _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker APEX II' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '3-circle goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 11273 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 31.60 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 31.60 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 1560 _reflns_number_gt 1487 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.1a (Crystal Impact, 2005)' _computing_publication_material 'SHELXTL (Bruker, 2006)' _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. Hydrogen atoms were located in the difference maps, but the following instructions were used in the SHELXL refinement in order to restrain the water bond lengths and angles to reasonable values. This was necessary because of low scattering factor of hydrogen. DFIX 0.82 0.03 O1 H1A DFIX 0.82 0.03 O1 H1B DANG 1.30 0.06 H1A H1B ; _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^)+(0.0407P)^2^+0.3963P] 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 SHELXL _refine_ls_extinction_coef 0.050(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1560 _refine_ls_number_parameters 77 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.424 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.134 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 0.204245(14) 0.7500 0.41433(3) 0.02388(11) Uani 1 2 d S . . F1 F 0.20418(8) 0.7500 0.66063(17) 0.0317(3) Uani 1 2 d S . . F2 F 0.20964(8) 0.7500 0.16802(16) 0.0297(3) Uani 1 2 d S . . O1 O 0.28486(8) 0.98274(19) 0.41505(13) 0.0341(3) Uani 1 1 d D . . H1A H 0.2844(13) 1.049(3) 0.333(3) 0.041 Uiso 1 1 d D . . H1B H 0.2849(13) 1.047(3) 0.495(3) 0.041 Uiso 1 1 d D . . N1 N 0.07946(11) 0.7500 0.4095(2) 0.0268(3) Uani 1 2 d S . . C2 C 0.03691(13) 0.7500 0.5597(3) 0.0292(4) Uani 1 2 d S . . H2 H 0.0644 0.7500 0.6661 0.035 Uiso 1 2 calc SR . . C3 C -0.04696(14) 0.7500 0.5596(3) 0.0340(4) Uani 1 2 d S . . Cl1 Cl -0.09800(4) 0.7500 0.75770(10) 0.0532(2) Uani 1 2 d S . . C4 C -0.08924(15) 0.7500 0.4056(4) 0.0443(6) Uani 1 2 d S . . H4 H -0.1455 0.7500 0.4046 0.053 Uiso 1 2 calc SR . . C5 C -0.04517(15) 0.7500 0.2509(3) 0.0480(7) Uani 1 2 d S . . H5 H -0.0717 0.7500 0.1433 0.058 Uiso 1 2 calc SR . . C6 C 0.03839(14) 0.7500 0.2577(3) 0.0371(5) Uani 1 2 d S . . H6 H 0.0673 0.7500 0.1531 0.045 Uiso 1 2 calc SR . . 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 0.02506(15) 0.03435(16) 0.01222(14) 0.000 0.00039(7) 0.000 F1 0.0356(7) 0.0456(7) 0.0140(5) 0.000 -0.0023(4) 0.000 F2 0.0372(6) 0.0392(7) 0.0129(5) 0.000 0.0021(4) 0.000 O1 0.0509(7) 0.0304(5) 0.0210(5) -0.0010(4) 0.0008(4) -0.0112(5) N1 0.0237(7) 0.0352(8) 0.0215(7) 0.000 -0.0008(5) 0.000 C2 0.0257(8) 0.0368(10) 0.0250(8) 0.000 0.0014(7) 0.000 C3 0.0265(9) 0.0367(10) 0.0387(11) 0.000 0.0077(8) 0.000 Cl1 0.0415(3) 0.0676(4) 0.0506(4) 0.000 0.0230(3) 0.000 C4 0.0246(10) 0.0557(15) 0.0527(16) 0.000 -0.0023(9) 0.000 C5 0.0317(11) 0.074(2) 0.0379(13) 0.000 -0.0117(10) 0.000 C6 0.0305(10) 0.0560(14) 0.0248(9) 0.000 -0.0045(8) 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 Cu1 F1 1.8790(13) . ? Cu1 F2 1.8812(12) . ? Cu1 N1 2.0617(18) . ? Cu1 O1 2.0807(12) 7_575 ? Cu1 O1 2.0807(12) . ? O1 H1A 0.775(19) . ? O1 H1B 0.750(19) . ? N1 C6 1.342(3) . ? N1 C2 1.344(3) . ? C2 C3 1.385(3) . ? C2 H2 0.9300 . ? C3 C4 1.367(4) . ? C3 Cl1 1.730(2) . ? C4 C5 1.387(4) . ? C4 H4 0.9300 . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 F1 Cu1 F2 177.32(6) . . ? F1 Cu1 N1 90.99(6) . . ? F2 Cu1 N1 91.69(6) . . ? F1 Cu1 O1 89.87(4) . 7_575 ? F2 Cu1 O1 88.41(4) . 7_575 ? N1 Cu1 O1 129.79(4) . 7_575 ? F1 Cu1 O1 89.87(4) . . ? F2 Cu1 O1 88.41(4) . . ? N1 Cu1 O1 129.79(4) . . ? O1 Cu1 O1 100.42(8) 7_575 . ? Cu1 O1 H1A 116.4(17) . . ? Cu1 O1 H1B 116.8(18) . . ? H1A O1 H1B 108(3) . . ? C6 N1 C2 118.1(2) . . ? C6 N1 Cu1 121.39(14) . . ? C2 N1 Cu1 120.50(14) . . ? N1 C2 C3 121.5(2) . . ? N1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 120.8(2) . . ? C4 C3 Cl1 120.12(19) . . ? C2 C3 Cl1 119.13(19) . . ? C3 C4 C5 117.6(2) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? C6 C5 C4 119.5(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? N1 C6 C5 122.5(2) . . ? N1 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? 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 F1 Cu1 N1 C6 180.0 . . . . ? F2 Cu1 N1 C6 0.0 . . . . ? O1 Cu1 N1 C6 -89.34(5) 7_575 . . . ? O1 Cu1 N1 C6 89.34(5) . . . . ? F1 Cu1 N1 C2 0.0 . . . . ? F2 Cu1 N1 C2 180.0 . . . . ? O1 Cu1 N1 C2 90.66(5) 7_575 . . . ? O1 Cu1 N1 C2 -90.66(5) . . . . ? C6 N1 C2 C3 0.0 . . . . ? Cu1 N1 C2 C3 180.0 . . . . ? N1 C2 C3 C4 0.0 . . . . ? N1 C2 C3 Cl1 180.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? Cl1 C3 C4 C5 180.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C2 N1 C6 C5 0.0 . . . . ? Cu1 N1 C6 C5 180.0 . . . . ? C4 C5 C6 N1 0.0 . . . . ? # END