# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef 'web_deposit_cif_file_0_MattiHaukka_1366691454.Kersen.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H22 N2, 2(Cl2 Cu)' _chemical_formula_sum 'C10 H22 Cl4 Cu2 N2' _chemical_formula_weight 439.18 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.4958(5) _cell_length_b 15.7766(10) _cell_length_c 5.9616(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.269(3) _cell_angle_gamma 90.00 _cell_volume 788.63(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3701 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 29.50 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.849 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 3.358 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5532 _exptl_absorpt_correction_T_max 0.8774 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'flat graphite crystal' _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on three-circle goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8107 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 29.60 _reflns_number_total 2206 _reflns_number_gt 1954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CrystaMaker (CrystalMaker Software ltd., 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0198P)^2^+0.3090P] 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 2206 _refine_ls_number_parameters 90 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0486 _refine_ls_wR_factor_gt 0.0465 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.67499(2) 0.768476(13) 0.22130(3) 0.02253(6) Uani 1 1 d . . . Cl1 Cl 0.76967(5) 0.66066(2) 0.44270(6) 0.02566(9) Uani 1 1 d . . . Cl2 Cl 0.44207(4) 0.83243(2) 0.28899(5) 0.01554(7) Uani 1 1 d . . . N1 N 0.33018(14) 0.86771(8) 0.7629(2) 0.0147(2) Uani 1 1 d . . . H1A H 0.386(2) 0.8460(12) 0.881(3) 0.026(5) Uiso 1 1 d . . . H1B H 0.366(2) 0.8498(11) 0.638(3) 0.019(4) Uiso 1 1 d . . . C2 C 0.16239(16) 0.83863(9) 0.7613(2) 0.0174(3) Uani 1 1 d . . . H2A H 0.1295 0.8523 0.9091 0.021 Uiso 1 1 calc R . . H2B H 0.1566 0.7764 0.7409 0.021 Uiso 1 1 calc R . . C3 C 0.04955(16) 0.88101(9) 0.5714(2) 0.0146(3) Uani 1 1 d . . . H3A H -0.0609 0.8622 0.5769 0.018 Uiso 1 1 calc R . . H3B H 0.0772 0.8636 0.4231 0.018 Uiso 1 1 calc R . . C4 C 0.05873(15) 0.97782(8) 0.5921(2) 0.0121(2) Uani 1 1 d . . . H4 H 0.0314 0.9940 0.7434 0.015 Uiso 1 1 calc R . . C5 C 0.34682(17) 0.96181(9) 0.7744(2) 0.0178(3) Uani 1 1 d . . . H5A H 0.4574 0.9777 0.7598 0.021 Uiso 1 1 calc R . . H5B H 0.3257 0.9820 0.9240 0.021 Uiso 1 1 calc R . . C6 C 0.23155(16) 1.00423(9) 0.5868(2) 0.0152(3) Uani 1 1 d . . . H6A H 0.2605 0.9889 0.4377 0.018 Uiso 1 1 calc R . . H6B H 0.2410 1.0665 0.6040 0.018 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 0.02222(11) 0.01816(11) 0.02660(11) 0.00192(7) 0.00207(7) -0.00112(7) Cl1 0.0312(2) 0.0254(2) 0.02325(18) 0.00626(14) 0.01293(14) 0.00991(16) Cl2 0.01778(16) 0.01645(17) 0.01291(14) -0.00012(11) 0.00407(11) -0.00068(12) N1 0.0149(5) 0.0164(6) 0.0125(5) 0.0019(4) 0.0012(4) 0.0042(5) C2 0.0161(6) 0.0162(7) 0.0201(7) 0.0058(5) 0.0039(5) 0.0019(5) C3 0.0134(6) 0.0121(7) 0.0177(6) 0.0021(5) 0.0006(5) 0.0006(5) C4 0.0127(6) 0.0116(7) 0.0119(6) -0.0001(4) 0.0012(4) 0.0019(5) C5 0.0163(7) 0.0155(7) 0.0196(7) -0.0014(5) -0.0037(5) 0.0013(5) C6 0.0136(6) 0.0119(7) 0.0190(6) 0.0016(5) -0.0011(5) -0.0002(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 Cl1 2.2227(4) . yes Cu1 Cl1 2.2552(4) 4_575 yes Cu1 Cl2 2.3138(4) . yes Cu1 Cu1 3.0373(2) 4_575 yes Cu1 Cu1 3.0373(2) 4_576 ? Cl1 Cu1 2.2552(4) 4_576 yes N1 C5 1.4919(19) . ? N1 C2 1.4961(18) . ? N1 H1A 0.86(2) . ? N1 H1B 0.895(19) . ? C2 C3 1.5157(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5333(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C4 1.530(2) 3_576 ? C4 C6 1.5314(18) . ? C4 H4 1.0000 . ? C5 C6 1.5180(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? 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 Cl1 132.75(2) . 4_575 ? Cl1 Cu1 Cl2 117.905(15) . . ? Cl1 Cu1 Cl2 109.194(16) 4_575 . ? Cl1 Cu1 Cu1 112.253(15) . 4_575 ? Cl1 Cu1 Cu1 46.843(11) 4_575 4_575 ? Cl2 Cu1 Cu1 112.958(10) . 4_575 ? Cl1 Cu1 Cu1 47.742(11) . 4_576 ? Cl1 Cu1 Cu1 150.964(13) 4_575 4_576 ? Cl2 Cu1 Cu1 77.136(10) . 4_576 ? Cu1 Cu1 Cu1 157.867(15) 4_575 4_576 ? Cu1 Cl1 Cu1 85.416(14) . 4_576 ? C5 N1 C2 112.87(11) . . ? C5 N1 H1A 108.9(13) . . ? C2 N1 H1A 106.6(13) . . ? C5 N1 H1B 108.0(12) . . ? C2 N1 H1B 110.3(12) . . ? H1A N1 H1B 110.2(18) . . ? N1 C2 C3 110.90(11) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 111.19(11) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C4 C4 C6 112.18(14) 3_576 . ? C4 C4 C3 112.28(13) 3_576 . ? C6 C4 C3 107.81(11) . . ? C4 C4 H4 108.1 3_576 . ? C6 C4 H4 108.1 . . ? C3 C4 H4 108.1 . . ? N1 C5 C6 111.08(11) . . ? N1 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N1 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C4 111.83(11) . . ? C5 C6 H6A 109.3 . . ? C4 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C4 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? 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 H1A Cl2 0.86(2) 2.41(2) 3.1766(12) 149.3(17) 1_556 yes N1 H1B Cl2 0.895(19) 2.291(19) 3.1717(12) 167.8(16) . yes _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.60 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.441 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 935268' ####################################################################### # # 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_2 #TrackingRef 'web_deposit_cif_file_0_MattiHaukka_1366691454.Kersen.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H22 N2, Cl4 Cu, H2 O' _chemical_formula_sum 'C10 H24 Cl4 Cu N2 O' _chemical_formula_weight 393.65 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' 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' 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2245(2) _cell_length_b 9.3525(2) _cell_length_c 9.6145(2) _cell_angle_alpha 76.7530(10) _cell_angle_beta 84.9900(10) _cell_angle_gamma 82.6010(10) _cell_volume 799.23(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9903 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 33.30 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 406 _exptl_absorpt_coefficient_mu 2.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4450 _exptl_absorpt_correction_T_max 0.7094 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'flat graphite crystal' _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on three-circle goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17070 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 33.33 _reflns_number_total 5955 _reflns_number_gt 5405 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CrystaMaker (CrystalMaker Software ltd., 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0181P)^2^+0.2591P] 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 5955 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0220 _refine_ls_R_factor_gt 0.0185 _refine_ls_wR_factor_ref 0.0469 _refine_ls_wR_factor_gt 0.0450 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.663718(13) 0.744053(12) 0.091496(12) 0.01105(3) Uani 1 1 d . . . Cl1 Cl 0.85417(3) 0.87744(3) 0.05965(3) 0.01586(5) Uani 1 1 d . . . Cl2 Cl 0.63921(2) 0.50109(2) 0.13401(2) 0.01298(4) Uani 1 1 d . . . Cl3 Cl 0.57967(3) 0.78803(3) 0.30705(2) 0.01599(5) Uani 1 1 d . . . Cl4 Cl 0.60261(3) 0.80740(2) -0.13755(2) 0.01421(4) Uani 1 1 d . . . O1S O 0.27131(10) 0.83425(10) 0.16718(12) 0.02754(19) Uani 1 1 d . . . H1SA H 0.241(2) 0.905(2) 0.116(2) 0.041(5) Uiso 1 1 d . . . H1SB H 0.343(2) 0.848(2) 0.197(2) 0.049(6) Uiso 1 1 d . . . N1 N 0.72066(9) 0.12222(10) 0.24259(9) 0.01432(15) Uani 1 1 d . . . N7 N 0.27844(9) 0.52985(10) 0.20415(9) 0.01386(15) Uani 1 1 d . . . C2 C 0.86787(11) 0.17564(11) 0.20427(11) 0.01579(17) Uani 1 1 d . . . H2A H 0.8645 0.2770 0.2200 0.019 Uiso 1 1 calc R . . H2B H 0.8948 0.1788 0.1017 0.019 Uiso 1 1 calc R . . C3 C 0.98202(10) 0.07371(10) 0.29506(10) 0.01340(16) Uani 1 1 d . . . H3A H 1.0776 0.1139 0.2720 0.016 Uiso 1 1 calc R . . H3B H 0.9926 -0.0245 0.2706 0.016 Uiso 1 1 calc R . . C4 C 0.94297(10) 0.05516(10) 0.45573(10) 0.01124(15) Uani 1 1 d . . . H4 H 0.9430 0.1534 0.4804 0.013 Uiso 1 1 calc R . . C5 C 0.78768(10) 0.00886(11) 0.48942(11) 0.01448(17) Uani 1 1 d . . . H5A H 0.7879 -0.0924 0.4743 0.017 Uiso 1 1 calc R . . H5B H 0.7588 0.0067 0.5914 0.017 Uiso 1 1 calc R . . C6 C 0.67564(11) 0.11250(11) 0.39712(11) 0.01491(17) Uani 1 1 d . . . H6A H 0.5785 0.0755 0.4189 0.018 Uiso 1 1 calc R . . H6B H 0.6676 0.2120 0.4185 0.018 Uiso 1 1 calc R . . C8 C 0.32373(11) 0.46971(11) 0.35402(10) 0.01468(17) Uani 1 1 d . . . H8A H 0.4188 0.5033 0.3647 0.018 Uiso 1 1 calc R . . H8B H 0.3365 0.3603 0.3739 0.018 Uiso 1 1 calc R . . C9 C 0.20924(10) 0.52137(11) 0.46070(10) 0.01302(16) Uani 1 1 d . . . H9A H 0.2023 0.6303 0.4454 0.016 Uiso 1 1 calc R . . H9B H 0.2400 0.4783 0.5591 0.016 Uiso 1 1 calc R . . C10 C 0.05857(10) 0.47613(10) 0.44555(10) 0.01108(15) Uani 1 1 d . . . H10 H 0.0677 0.3659 0.4619 0.013 Uiso 1 1 calc R . . C11 C 0.01665(11) 0.54086(11) 0.29125(10) 0.01441(17) Uani 1 1 d . . . H11A H -0.0788 0.5095 0.2781 0.017 Uiso 1 1 calc R . . H11B H 0.0051 0.6501 0.2739 0.017 Uiso 1 1 calc R . . C12 C 0.13063(11) 0.49184(12) 0.18254(11) 0.01614(17) Uani 1 1 d . . . H12A H 0.1346 0.3837 0.1924 0.019 Uiso 1 1 calc R . . H12B H 0.1022 0.5409 0.0846 0.019 Uiso 1 1 calc R . . H7A H 0.3409(17) 0.4965(16) 0.1482(16) 0.022(4) Uiso 1 1 d . . . H7B H 0.2776(16) 0.6286(17) 0.1811(16) 0.023(4) Uiso 1 1 d . . . H1A H 0.7210(17) 0.0344(18) 0.2223(17) 0.028(4) Uiso 1 1 d . . . H1B H 0.6547(18) 0.1783(17) 0.1934(17) 0.027(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01241(5) 0.01111(5) 0.00999(5) -0.00211(4) -0.00105(4) -0.00281(4) Cl1 0.01495(10) 0.01839(10) 0.01527(10) -0.00299(8) -0.00106(8) -0.00690(8) Cl2 0.01370(10) 0.01102(9) 0.01394(10) -0.00238(7) 0.00091(7) -0.00224(7) Cl3 0.01971(11) 0.01637(10) 0.01226(10) -0.00463(7) 0.00051(8) -0.00174(8) Cl4 0.01508(10) 0.01525(9) 0.01220(10) -0.00202(7) -0.00387(8) -0.00112(7) O1S 0.0212(4) 0.0163(4) 0.0438(6) -0.0015(4) -0.0090(4) -0.0017(3) N1 0.0118(4) 0.0164(4) 0.0146(4) -0.0031(3) -0.0034(3) 0.0006(3) N7 0.0124(4) 0.0161(4) 0.0124(4) -0.0030(3) 0.0031(3) -0.0017(3) C2 0.0126(4) 0.0175(4) 0.0150(4) 0.0009(3) -0.0011(3) -0.0010(3) C3 0.0109(4) 0.0161(4) 0.0122(4) -0.0018(3) -0.0013(3) 0.0002(3) C4 0.0105(4) 0.0114(4) 0.0124(4) -0.0036(3) -0.0015(3) -0.0011(3) C5 0.0108(4) 0.0182(4) 0.0136(4) -0.0015(3) -0.0011(3) -0.0018(3) C6 0.0115(4) 0.0192(4) 0.0137(4) -0.0040(3) -0.0008(3) 0.0003(3) C8 0.0113(4) 0.0184(4) 0.0134(4) -0.0031(3) 0.0007(3) 0.0002(3) C9 0.0102(4) 0.0166(4) 0.0124(4) -0.0041(3) 0.0009(3) -0.0013(3) C10 0.0107(4) 0.0107(4) 0.0114(4) -0.0023(3) 0.0009(3) -0.0008(3) C11 0.0116(4) 0.0194(4) 0.0118(4) -0.0035(3) 0.0000(3) -0.0004(3) C12 0.0131(4) 0.0239(5) 0.0128(4) -0.0066(3) 0.0009(3) -0.0036(3) _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 Cl1 2.2432(3) . yes Cu1 Cl4 2.2475(3) . yes Cu1 Cl2 2.2521(2) . yes Cu1 Cl3 2.2568(3) . yes O1S H1SA 0.77(2) . ? O1S H1SB 0.78(2) . ? N1 C6 1.4927(13) . ? N1 C2 1.4941(13) . ? N1 H1A 0.886(16) . ? N1 H1B 0.850(16) . ? N7 C12 1.4956(13) . ? N7 C8 1.4968(13) . ? N7 H7A 0.833(15) . ? N7 H7B 0.898(15) . ? C2 C3 1.5166(14) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5304(13) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5359(13) . ? C4 C4 1.5396(18) 2_756 ? C4 H4 1.0000 . ? C5 C6 1.5177(14) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 C9 1.5190(13) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5319(13) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5314(14) . ? C10 C10 1.5349(18) 2_566 ? C10 H10 1.0000 . ? C11 C12 1.5204(13) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? 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 Cl4 96.004(10) . . ? Cl1 Cu1 Cl2 134.842(10) . . ? Cl4 Cu1 Cl2 98.472(9) . . ? Cl1 Cu1 Cl3 96.955(10) . . ? Cl4 Cu1 Cl3 139.402(10) . . ? Cl2 Cu1 Cl3 99.129(9) . . ? H1SA O1S H1SB 109.7(19) . . ? C6 N1 C2 111.91(8) . . ? C6 N1 H1A 109.4(10) . . ? C2 N1 H1A 110.1(10) . . ? C6 N1 H1B 108.0(10) . . ? C2 N1 H1B 111.8(11) . . ? H1A N1 H1B 105.4(14) . . ? C12 N7 C8 112.57(8) . . ? C12 N7 H7A 109.8(10) . . ? C8 N7 H7A 108.6(10) . . ? C12 N7 H7B 108.8(10) . . ? C8 N7 H7B 110.4(9) . . ? H7A N7 H7B 106.5(13) . . ? N1 C2 C3 110.22(8) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 112.75(8) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C3 C4 C5 109.22(8) . . ? C3 C4 C4 111.29(9) . 2_756 ? C5 C4 C4 112.13(9) . 2_756 ? C3 C4 H4 108.0 . . ? C5 C4 H4 108.0 . . ? C4 C4 H4 108.0 2_756 . ? C6 C5 C4 112.55(8) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? N1 C6 C5 109.88(8) . . ? N1 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? N1 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N7 C8 C9 110.58(8) . . ? N7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 111.65(8) . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 107.84(7) . . ? C11 C10 C10 111.82(9) . 2_566 ? C9 C10 C10 112.76(9) . 2_566 ? C11 C10 H10 108.1 . . ? C9 C10 H10 108.1 . . ? C10 C10 H10 108.1 2_566 . ? C12 C11 C10 112.24(8) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N7 C12 C11 110.83(8) . . ? N7 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? N7 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? 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 O1S H1SA Cl1 0.77(2) 2.45(2) 3.2107(10) 176.7(18) 2_675 yes O1S H1SB Cl3 0.78(2) 2.45(2) 3.1892(10) 158.2(19) . yes N7 H7A Cl2 0.833(15) 2.699(15) 3.3428(9) 135.3(13) 2_665 yes N7 H7A Cl2 0.833(15) 2.749(15) 3.3261(9) 127.9(12) . yes N7 H7A Cl4 0.833(15) 2.847(15) 3.3874(9) 124.3(12) 2_665 yes N7 H7B O1S 0.898(15) 1.891(15) 2.7798(12) 170.0(14) . yes N1 H1A Cl1 0.886(16) 2.522(16) 3.2546(9) 140.4(13) 1_545 yes N1 H1A Cl3 0.886(16) 2.720(16) 3.4443(9) 139.7(13) 1_545 yes N1 H1B Cl4 0.850(16) 2.460(16) 3.1719(9) 141.8(14) 2_665 yes N1 H1B Cl2 0.850(16) 2.928(16) 3.4592(9) 122.4(12) . yes _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 33.33 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.426 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 935269' ####################################################################### # # 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_3 #TrackingRef 'web_deposit_cif_file_0_MattiHaukka_1366691454.Kersen.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H12 N2, Cl4 Cu' _chemical_formula_sum 'C4 H12 Cl4 Cu N2' _chemical_formula_weight 293.50 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' 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 tetragonal _symmetry_space_group_name_H-M 'P 43 21 2' _symmetry_space_group_name_Hall 'P 4nw 2abw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' '-x, -y, z+1/2' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 7.6443(4) _cell_length_b 7.6443(4) _cell_length_c 19.1597(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1119.60(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4049 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 30.07 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.49 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 2.853 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2192 _exptl_absorpt_correction_T_max 0.3378 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'flat graphite crystal' _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on three-circle goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5271 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 29.00 _reflns_number_total 1474 _reflns_number_gt 1420 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CrystaMaker (CrystalMaker Software ltd., 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0090P)^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 SHELXL _refine_ls_extinction_coef 0.0034(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.027(10) _refine_ls_number_reflns 1474 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0163 _refine_ls_R_factor_gt 0.0154 _refine_ls_wR_factor_ref 0.0368 _refine_ls_wR_factor_gt 0.0366 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 Cl1 Cl 0.34334(6) 0.63846(5) 0.567998(15) 0.01932(10) Uani 1 1 d . . . Cu1 Cu 0.40577(2) 0.40577(2) 0.5000 0.01419(8) Uani 1 2 d S . . Cl2 Cl 0.20831(5) 0.45012(5) 0.415805(16) 0.01663(9) Uani 1 1 d . . . N1 N 0.44883(18) 0.31448(18) 0.28323(6) 0.0154(3) Uani 1 1 d . . . C2 C 0.38422(18) 0.47649(19) 0.24856(7) 0.0155(3) Uani 1 1 d . . . H2A H 0.2773 0.5185 0.2724 0.019 Uiso 1 1 calc R . . H2B H 0.3543 0.4510 0.1993 0.019 Uiso 1 1 calc R . . C6 C 0.61235(18) 0.24702(19) 0.25025(8) 0.0172(3) Uani 1 1 d . . . H6A H 0.5873 0.2097 0.2018 0.021 Uiso 1 1 calc R . . H6B H 0.6548 0.1439 0.2765 0.021 Uiso 1 1 calc R . . H1A H 0.467(2) 0.335(2) 0.3269(9) 0.028(5) Uiso 1 1 d . . . H1B H 0.366(2) 0.240(2) 0.2808(8) 0.023(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0297(2) 0.0156(2) 0.01265(14) -0.00167(12) -0.00323(13) 0.00510(16) Cu1 0.01593(11) 0.01593(11) 0.01071(10) -0.00038(7) 0.00038(7) 0.00269(11) Cl2 0.0174(2) 0.0189(2) 0.01356(14) -0.00226(13) -0.00164(13) 0.00362(16) N1 0.0176(8) 0.0156(7) 0.0130(5) 0.0019(5) 0.0006(5) -0.0044(6) C2 0.0130(8) 0.0184(8) 0.0150(5) 0.0026(6) 0.0001(6) 0.0013(6) C6 0.0211(8) 0.0143(8) 0.0160(5) 0.0011(6) 0.0031(6) 0.0038(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 Cl1 Cu1 2.2559(4) . yes Cu1 Cl2 2.2351(4) . yes Cu1 Cl2 2.2351(4) 7_556 ? Cu1 Cl1 2.2559(4) 7_556 ? N1 C2 1.4897(19) . ? N1 C6 1.4926(18) . ? N1 H1A 0.862(17) . ? N1 H1B 0.852(17) . ? C2 C2 1.507(3) 8_665 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C6 C6 1.520(3) 8_665 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? 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 Cl2 Cu1 Cl2 136.54(2) . 7_556 ? Cl2 Cu1 Cl1 98.879(14) . . ? Cl2 Cu1 Cl1 98.497(13) 7_556 . ? Cl2 Cu1 Cl1 98.498(13) . 7_556 ? Cl2 Cu1 Cl1 98.879(13) 7_556 7_556 ? Cl1 Cu1 Cl1 131.85(2) . 7_556 ? C2 N1 C6 112.09(10) . . ? C2 N1 H1A 109.8(12) . . ? C6 N1 H1A 109.5(13) . . ? C2 N1 H1B 106.6(12) . . ? C6 N1 H1B 111.5(12) . . ? H1A N1 H1B 107.2(16) . . ? N1 C2 C2 109.68(10) . 8_665 ? N1 C2 H2A 109.7 . . ? C2 C2 H2A 109.7 8_665 . ? N1 C2 H2B 109.7 . . ? C2 C2 H2B 109.7 8_665 . ? H2A C2 H2B 108.2 . . ? N1 C6 C6 110.52(9) . 8_665 ? N1 C6 H6A 109.5 . . ? C6 C6 H6A 109.5 8_665 . ? N1 C6 H6B 109.5 . . ? C6 C6 H6B 109.5 8_665 . ? H6A C6 H6B 108.1 . . ? 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 H1A Cl1 0.862(17) 2.402(17) 3.2054(13) 155.2(17) 7_556 yes N1 H1A Cl2 0.862(17) 2.758(18) 3.3027(13) 122.5(15) . yes N1 H1B Cl2 0.852(17) 2.505(18) 3.1865(14) 137.6(14) 5_545 yes N1 H1B Cl1 0.852(17) 2.598(16) 3.2497(14) 134.1(13) 5_545 yes _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.288 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 935270' ####################################################################### # # 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_4 #TrackingRef 'web_deposit_cif_file_0_MattiHaukka_1366691454.Kersen.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H12 N2, Cl3 Cu' _chemical_formula_sum 'C4 H12 Cl3 Cu N2' _chemical_formula_weight 258.05 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.9151(9) _cell_length_b 6.7334(6) _cell_length_c 12.1914(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.197(5) _cell_angle_gamma 90.00 _cell_volume 890.78(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1927 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 32.82 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.924 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 3.281 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5165 _exptl_absorpt_correction_T_max 0.6942 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'flat graphite crystal' _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on three-circle goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5934 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 33.21 _reflns_number_total 1706 _reflns_number_gt 1331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CrystaMaker (CrystalMaker Software ltd., 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0207P)^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 1706 _refine_ls_number_parameters 55 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.5000 0.56911(6) 0.2500 0.01667(10) Uani 1 2 d S . . Cl1 Cl 0.5000 0.89275(11) 0.2500 0.01344(14) Uani 1 2 d S . . Cl2 Cl 0.39425(4) 0.36977(8) 0.35828(3) 0.01266(11) Uani 1 1 d . . . N1 N 0.19380(13) 0.6933(3) 0.39299(11) 0.0106(3) Uani 1 1 d . . . H1A H 0.1322(19) 0.695(4) 0.3393(17) 0.015(5) Uiso 1 1 d . . . H1B H 0.243(2) 0.621(4) 0.3666(18) 0.021(6) Uiso 1 1 d . . . C2 C 0.15069(15) 0.6071(3) 0.49511(14) 0.0129(4) Uani 1 1 d . . . H2A H 0.1200 0.4704 0.4800 0.015 Uiso 1 1 calc R . . H2B H 0.0819 0.6879 0.5178 0.015 Uiso 1 1 calc R . . C6 C 0.25543(15) 0.6033(3) 0.58733(14) 0.0120(4) Uani 1 1 d . . . H6A H 0.2251 0.5523 0.6556 0.014 Uiso 1 1 calc R . . H6B H 0.3212 0.5133 0.5673 0.014 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 0.01653(15) 0.0102(2) 0.02149(17) 0.000 -0.00608(12) 0.000 Cl1 0.0152(2) 0.0094(4) 0.0154(3) 0.000 0.0003(2) 0.000 Cl2 0.01377(17) 0.0111(3) 0.01306(18) 0.00007(17) 0.00131(14) 0.00216(17) N1 0.0123(6) 0.0099(10) 0.0092(6) -0.0010(6) -0.0008(5) 0.0016(6) C2 0.0119(7) 0.0140(12) 0.0126(7) 0.0023(7) 0.0002(6) -0.0049(7) C6 0.0133(7) 0.0116(11) 0.0110(7) 0.0031(7) 0.0002(6) 0.0001(7) _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 Cl1 2.1792(9) . yes Cu1 Cl2 2.2816(5) . yes Cu1 Cl2 2.2816(5) 2_655 ? N1 C6 1.487(3) 7_566 ? N1 C2 1.495(2) . ? N1 H1A 0.89(2) . ? N1 H1B 0.82(3) . ? C2 C6 1.515(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C6 N1 1.487(3) 7_566 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? 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 126.036(15) . . ? Cl1 Cu1 Cl2 126.035(15) . 2_655 ? Cl2 Cu1 Cl2 107.93(3) . 2_655 ? C6 N1 C2 111.61(14) 7_566 . ? C6 N1 H1A 110.4(17) 7_566 . ? C2 N1 H1A 109.7(14) . . ? C6 N1 H1B 111.4(17) 7_566 . ? C2 N1 H1B 112.0(17) . . ? H1A N1 H1B 101(2) . . ? N1 C2 C6 110.15(14) . . ? N1 C2 H2A 109.6 . . ? C6 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C6 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N1 C6 C2 110.03(16) 7_566 . ? N1 C6 H6A 109.7 7_566 . ? C2 C6 H6A 109.7 . . ? N1 C6 H6B 109.7 7_566 . ? C2 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? 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 H1A Cl1 0.89(2) 2.66(2) 3.2882(17) 129(2) 3_445 yes N1 H1A Cl2 0.89(2) 2.67(2) 3.3293(15) 132.1(18) 4 yes N1 H1A Cl2 0.89(2) 2.88(2) 3.4616(16) 124.2(16) 3_455 yes N1 H1B Cl2 0.82(3) 2.37(3) 3.1483(18) 159(2) . yes _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 33.21 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.575 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.141 _database_code_depnum_ccdc_archive 'CCDC 935271'