# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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 #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; '[Cu2(1-tza)4]BrH3O1/3H2O' ; _chemical_name_common {[Cu2(1-tza)4].Br.H3O.1/3H2O} _chemical_melting_point 'not measured' _chemical_formula_moiety 'C12 H15.67 Br Cu2 N16 O9.33' _chemical_formula_sum 'C12 H15.67 Br Cu2 N16 O9.33' _chemical_formula_weight 740.41 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' Br Br -0.2901 2.4595 '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' 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 trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 16.5929(16) _cell_length_b 16.5929(16) _cell_length_c 33.137(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7901.1(16) _cell_formula_units_Z 9 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6234 _cell_measurement_theta_min 2.4550 _cell_measurement_theta_max 27.4855 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3305 _exptl_absorpt_coefficient_mu 2.406 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6640 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn70 (4x4 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19763 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3255 _reflns_number_gt 2643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. PROBLEM: Structure Contains Solvent Accessible VOIDS of . 2479 Ang3 RESPONSE: The voids are channels running along the trigonal c axis of the porous crystal. These voids are partially occupied by disordered guest molecules. After including four electron density peaks as bromine anions (Br1 and Br2) and lattice water molecules (O1W and O2W), no further electron density above ca. 1 e/A3 is observed. ; _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^)+(0.1149P)^2^+30.5863P] 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 3255 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1779 _refine_ls_wR_factor_gt 0.1663 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.49562(3) 1.02427(3) 0.949220(15) 0.03110(13) Uani 1 1 d . . . O21 O 0.88115(16) 1.35669(17) 0.92501(8) 0.0341(6) Uani 1 1 d . . . O22 O 0.9550(2) 1.3955(2) 0.86598(10) 0.0624(11) Uani 1 1 d . . . O11 O 0.06045(17) 0.57915(17) 0.98118(9) 0.0351(7) Uani 1 1 d . . . O12 O 0.1423(2) 0.6630(2) 0.92816(10) 0.0597(10) Uani 1 1 d . . . N24 N 0.6313(2) 1.0963(2) 0.93291(11) 0.0369(8) Uani 1 1 d . . . N23 N 0.6931(2) 1.0667(2) 0.94090(14) 0.0550(11) Uani 1 1 d . . . N21 N 0.7567(2) 1.1804(2) 0.89996(11) 0.0399(9) Uani 1 1 d . . . N22 N 0.7690(2) 1.1169(3) 0.92103(15) 0.0579(12) Uani 1 1 d . . . N14 N 0.3579(2) 0.9338(2) 0.95209(11) 0.0350(8) Uani 1 1 d . . . N11 N 0.2266(2) 0.8238(2) 0.97267(11) 0.0368(8) Uani 1 1 d . . . N13 N 0.2909(2) 0.9572(2) 0.94526(15) 0.0572(12) Uani 1 1 d . . . N12 N 0.2121(2) 0.8904(3) 0.95789(15) 0.0597(12) Uani 1 1 d . . . C21 C 0.6724(3) 1.1668(3) 0.90835(13) 0.0393(10) Uani 1 1 d . . . H21A H 0.6470 1.2016 0.8984 0.047 Uiso 1 1 calc R . . C22 C 0.8293(3) 1.2452(3) 0.87235(15) 0.0521(13) Uani 1 1 d . . . H22B H 0.7994 1.2520 0.8485 0.062 Uiso 1 1 calc R . . H22A H 0.8661 1.2176 0.8639 0.062 Uiso 1 1 calc R . . C23 C 0.8952(2) 1.3421(3) 0.88910(13) 0.0365(10) Uani 1 1 d . . . C11 C 0.3156(3) 0.8512(3) 0.96891(13) 0.0381(10) Uani 1 1 d . . . H11A H 0.3439 0.8175 0.9769 0.046 Uiso 1 1 calc R . . C12 C 0.1538(3) 0.7393(3) 0.99097(14) 0.0449(12) Uani 1 1 d . . . H12B H 0.1024 0.7484 0.9983 0.070(16) Uiso 1 1 d R . . H12A H 0.1776 0.7269 1.0156 0.032(11) Uiso 1 1 d R . . C13 C 0.1182(2) 0.6557(3) 0.96302(14) 0.0376(10) Uani 1 1 d . . . Br1 Br 0.3333 0.6667 1.01655(3) 0.0462(2) Uani 1 3 d S . . Br2 Br 1.6667 1.3333 0.8333 0.0488(3) Uani 1 6 d S . . O1W O 1.3333 1.6667 0.8925(8) 0.162(10) Uani 0.50 3 d SP . . O2W O 1.116(2) 1.5557(11) 0.8578(4) 0.355(18) Uani 0.50 1 d P . . 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 0.0278(2) 0.01904(19) 0.0453(3) 0.00449(17) 0.00168(18) 0.01076(15) O21 0.0206(11) 0.0290(12) 0.0457(16) -0.0042(11) -0.0056(11) 0.0072(9) O22 0.0488(18) 0.0538(19) 0.0517(19) 0.0140(16) 0.0033(16) 0.0010(16) O11 0.0246(11) 0.0213(11) 0.0494(16) -0.0003(11) -0.0027(11) 0.0040(9) O12 0.0633(19) 0.0474(17) 0.0482(19) -0.0017(15) 0.0134(16) 0.0126(15) N24 0.0310(14) 0.0237(14) 0.053(2) 0.0037(13) 0.0020(15) 0.0114(12) N23 0.0346(16) 0.0373(17) 0.094(3) 0.0164(19) 0.0053(19) 0.0185(14) N21 0.0331(16) 0.0270(15) 0.048(2) -0.0045(14) 0.0033(15) 0.0061(13) N22 0.0383(17) 0.0453(19) 0.093(3) 0.007(2) 0.011(2) 0.0228(15) N14 0.0306(14) 0.0234(13) 0.0485(19) 0.0045(13) -0.0003(14) 0.0116(11) N11 0.0310(15) 0.0211(14) 0.048(2) 0.0029(13) 0.0010(14) 0.0057(12) N13 0.0349(17) 0.0337(17) 0.096(3) 0.0189(19) -0.005(2) 0.0115(14) N12 0.0294(16) 0.0379(18) 0.107(3) 0.020(2) 0.002(2) 0.0132(14) C21 0.0328(17) 0.0329(18) 0.049(2) 0.0030(17) 0.0008(18) 0.0138(15) C22 0.040(2) 0.043(2) 0.052(3) -0.006(2) 0.014(2) 0.0047(19) C23 0.0225(15) 0.0371(19) 0.041(2) 0.0019(17) -0.0075(16) 0.0081(15) C11 0.0324(18) 0.0250(17) 0.050(2) 0.0026(16) -0.0013(17) 0.0091(14) C12 0.035(2) 0.0219(18) 0.058(3) 0.0019(18) 0.011(2) -0.0006(16) C13 0.0231(16) 0.0302(18) 0.054(3) -0.0001(17) -0.0023(17) 0.0093(14) Br1 0.0364(2) 0.0364(2) 0.0658(5) 0.000 0.000 0.01822(12) Br2 0.0499(4) 0.0499(4) 0.0466(6) 0.000 0.000 0.02497(19) O1W 0.174(15) 0.174(15) 0.138(19) 0.000 0.000 0.087(7) O2W 0.50(3) 0.137(13) 0.072(8) -0.024(8) 0.036(14) -0.112(17) _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 O21 1.934(2) 3_575 ? Cu1 O11 1.945(2) 3_565 ? Cu1 N14 2.013(3) . ? Cu1 N24 2.025(3) . ? Cu1 O11 2.425(3) 12_667 ? Cu1 Cu1 3.4803(11) 10_677 ? O21 C23 1.259(5) . ? O21 Cu1 1.934(2) 2_775 ? O22 C23 1.216(5) . ? O11 C13 1.295(5) . ? O11 Cu1 1.945(2) 2_665 ? O11 Cu1 2.425(3) 11_457 ? O12 C13 1.209(5) . ? N24 C21 1.303(5) . ? N24 N23 1.365(5) . ? N23 N22 1.290(5) . ? N21 C21 1.330(5) . ? N21 N22 1.361(6) . ? N21 C22 1.466(5) . ? N14 C11 1.311(5) . ? N14 N13 1.369(5) . ? N11 C11 1.316(5) . ? N11 N12 1.336(5) . ? N11 C12 1.448(5) . ? N13 N12 1.290(5) . ? C22 C23 1.526(6) . ? C12 C13 1.520(6) . ? 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 O21 Cu1 O11 171.28(12) 3_575 3_565 ? O21 Cu1 N14 91.90(13) 3_575 . ? O11 Cu1 N14 89.73(13) 3_565 . ? O21 Cu1 N24 90.14(13) 3_575 . ? O11 Cu1 N24 90.52(13) 3_565 . ? N14 Cu1 N24 164.84(15) . . ? O21 Cu1 O11 96.64(10) 3_575 12_667 ? O11 Cu1 O11 74.94(10) 3_565 12_667 ? N14 Cu1 O11 85.68(12) . 12_667 ? N24 Cu1 O11 109.00(13) . 12_667 ? O21 Cu1 Cu1 129.27(9) 3_575 10_677 ? O11 Cu1 Cu1 42.28(8) 3_565 10_677 ? N14 Cu1 Cu1 86.84(10) . 10_677 ? N24 Cu1 Cu1 103.41(10) . 10_677 ? O11 Cu1 Cu1 32.66(6) 12_667 10_677 ? C23 O21 Cu1 116.3(2) . 2_775 ? C13 O11 Cu1 119.3(3) . 2_665 ? C13 O11 Cu1 135.6(3) . 11_457 ? Cu1 O11 Cu1 105.06(10) 2_665 11_457 ? C21 N24 N23 107.1(3) . . ? C21 N24 Cu1 128.7(3) . . ? N23 N24 Cu1 123.3(2) . . ? N22 N23 N24 109.6(4) . . ? C21 N21 N22 108.3(3) . . ? C21 N21 C22 131.6(4) . . ? N22 N21 C22 120.1(4) . . ? N23 N22 N21 106.6(4) . . ? C11 N14 N13 106.3(3) . . ? C11 N14 Cu1 127.9(3) . . ? N13 N14 Cu1 124.1(2) . . ? C11 N11 N12 108.3(3) . . ? C11 N11 C12 128.5(4) . . ? N12 N11 C12 123.1(4) . . ? N12 N13 N14 108.7(3) . . ? N13 N12 N11 107.8(4) . . ? N24 C21 N21 108.5(4) . . ? N21 C22 C23 116.0(4) . . ? O22 C23 O21 128.1(4) . . ? O22 C23 C22 115.7(4) . . ? O21 C23 C22 116.2(3) . . ? N14 C11 N11 108.9(4) . . ? N11 C12 C13 112.6(4) . . ? O12 C13 O11 126.0(4) . . ? O12 C13 C12 122.2(4) . . ? O11 C13 C12 111.8(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.864 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.121 _database_code_depnum_ccdc_archive 'CCDC 942747' ####################################################################### # # 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 #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu2(1-tza)4]BF4.H3O.H2O' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C12 H19 B Cu2 F4 N16 O10' _chemical_formula_sum 'C12 H19 B Cu2 F4 N16 O10' _chemical_formula_weight 761.32 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I4(1)/a _symmetry_space_group_name_hall '-I 4ad ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 24.074(4) _cell_length_b 24.074(4) _cell_length_c 5.1021(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2957.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3517 _cell_measurement_theta_min 2.3929 _cell_measurement_theta_max 27.1190 _exptl_crystal_description Prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.710 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 1.537 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8260 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn70 (4x4 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8629 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1289 _reflns_number_gt 1010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1085P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1289 _refine_ls_number_parameters 117 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1875 _refine_ls_wR_factor_gt 0.1710 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.091 _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 0.0000 0.0000 0.04389(16) Uani 1 2 d S . . C3 C 0.56737(14) -0.08841(12) -0.1224(6) 0.0506(9) Uani 1 1 d . . . O2 O 0.51884(9) -0.06985(8) -0.1813(5) 0.0538(6) Uani 1 1 d . . . N1 N 0.64082(12) -0.16023(12) -0.2238(5) 0.0535(8) Uani 1 1 d . . . C2 C 0.58720(13) -0.13529(14) -0.3106(7) 0.0556(9) Uani 1 1 d . . . H2A H 0.5591 -0.1641 -0.3183 0.067 Uiso 1 1 calc R . . H2B H 0.5916 -0.1202 -0.4856 0.067 Uiso 1 1 calc R . . N2 N 0.69011(13) -0.14564(13) -0.3344(6) 0.0782(10) Uani 1 1 d . . . O1 O 0.59718(12) -0.07204(12) 0.0571(5) 0.0840(9) Uani 1 1 d . . . F1 F 0.52881(14) -0.21254(15) -0.7300(7) 0.1506(14) Uani 1 1 d . . . B1 B 0.5000 -0.2500 -0.8750 0.055(2) Uani 1 4 d S . . O1WA O 0.7126(6) -0.0543(5) 0.138(3) 0.112(4) Uani 0.25 1 d PU . . O1WB O 0.7012(8) -0.0150(9) 0.295(4) 0.161(4) Uani 0.25 1 d PU . . N3 N 0.72908(13) -0.17117(14) -0.2060(6) 0.0808(10) Uani 1 1 d . . . N4 N 0.70637(10) -0.20252(11) -0.0065(5) 0.0472(7) Uani 1 1 d . . . C1 C 0.65123(13) -0.19448(13) -0.0240(6) 0.0497(9) Uani 1 1 d . . . H1A H 0.6246 -0.2102 0.0854 0.060 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 0.0437(3) 0.0374(3) 0.0506(3) 0.0001(2) 0.0038(2) 0.0022(2) C3 0.0659(19) 0.0386(15) 0.0473(17) 0.0003(14) 0.0062(16) 0.0059(15) O2 0.0552(12) 0.0413(11) 0.0649(13) -0.0004(10) 0.0089(11) 0.0072(10) N1 0.0555(15) 0.0591(15) 0.0458(14) 0.0025(13) 0.0052(12) 0.0100(14) C2 0.0555(18) 0.0586(18) 0.0526(17) -0.0025(17) -0.0058(16) 0.0187(16) N2 0.0685(18) 0.091(2) 0.0757(18) 0.0397(17) 0.0174(17) 0.0221(17) O1 0.0921(18) 0.0879(17) 0.0720(15) -0.0334(14) -0.0193(15) 0.0236(16) F1 0.120(2) 0.162(3) 0.170(3) -0.073(2) -0.032(2) -0.014(2) B1 0.041(2) 0.041(2) 0.084(5) 0.000 0.000 0.000 O1WA 0.119(6) 0.108(6) 0.110(6) -0.010(5) 0.010(5) -0.009(5) O1WB 0.160(7) 0.158(7) 0.164(7) -0.001(5) -0.009(6) -0.002(6) N3 0.0513(16) 0.102(2) 0.089(2) 0.0409(18) 0.0242(16) 0.0206(17) N4 0.0395(12) 0.0485(14) 0.0535(15) 0.0081(12) 0.0035(12) 0.0012(12) C1 0.0486(17) 0.0494(17) 0.0512(18) 0.0015(15) 0.0011(15) 0.0013(15) _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 O2 1.972(2) 9_655 ? Cu1 O2 1.972(2) . ? Cu1 N4 2.030(2) 4_554 ? Cu1 N4 2.030(2) 12_656 ? C3 O1 1.228(4) . ? C3 O2 1.286(4) . ? C3 C2 1.557(5) . ? N1 C1 1.335(4) . ? N1 N2 1.360(4) . ? N1 C2 1.491(4) . ? N2 N3 1.299(4) . ? F1 B1 1.357(3) . ? B1 F1 1.357(3) 12_654 ? B1 F1 1.357(3) 6_544 ? B1 F1 1.357(3) 15_653 ? O1WA O1WB 1.27(2) . ? N3 N4 1.380(4) . ? N4 C1 1.344(4) . ? N4 Cu1 2.030(2) 3_545 ? 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 O2 Cu1 O2 180.00(18) 9_655 . ? O2 Cu1 N4 89.47(10) 9_655 4_554 ? O2 Cu1 N4 90.53(10) . 4_554 ? O2 Cu1 N4 90.53(10) 9_655 12_656 ? O2 Cu1 N4 89.47(10) . 12_656 ? N4 Cu1 N4 180.00(17) 4_554 12_656 ? O1 C3 O2 126.4(3) . . ? O1 C3 C2 120.9(3) . . ? O2 C3 C2 112.7(3) . . ? C3 O2 Cu1 113.3(2) . . ? C1 N1 N2 108.2(3) . . ? C1 N1 C2 129.6(3) . . ? N2 N1 C2 121.9(3) . . ? N1 C2 C3 112.0(3) . . ? N3 N2 N1 107.4(3) . . ? F1 B1 F1 107.29(14) . 12_654 ? F1 B1 F1 113.9(3) . 6_544 ? F1 B1 F1 107.29(15) 12_654 6_544 ? F1 B1 F1 107.29(15) . 15_653 ? F1 B1 F1 113.9(3) 12_654 15_653 ? F1 B1 F1 107.29(14) 6_544 15_653 ? N2 N3 N4 110.2(3) . . ? C1 N4 N3 105.3(2) . . ? C1 N4 Cu1 129.4(2) . 3_545 ? N3 N4 Cu1 125.3(2) . 3_545 ? N1 C1 N4 109.0(3) . . ? 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 O1 C3 O2 Cu1 11.9(4) . . . . ? C2 C3 O2 Cu1 -166.9(2) . . . . ? O2 Cu1 O2 C3 -160(32) 9_655 . . . ? N4 Cu1 O2 C3 78.4(2) 4_554 . . . ? N4 Cu1 O2 C3 -101.6(2) 12_656 . . . ? C1 N1 C2 C3 73.4(4) . . . . ? N2 N1 C2 C3 -100.1(3) . . . . ? O1 C3 C2 N1 6.9(4) . . . . ? O2 C3 C2 N1 -174.2(3) . . . . ? C1 N1 N2 N3 0.8(4) . . . . ? C2 N1 N2 N3 175.6(3) . . . . ? N1 N2 N3 N4 -0.7(4) . . . . ? N2 N3 N4 C1 0.4(4) . . . . ? N2 N3 N4 Cu1 -179.9(2) . . . 3_545 ? N2 N1 C1 N4 -0.6(4) . . . . ? C2 N1 C1 N4 -174.8(3) . . . . ? N3 N4 C1 N1 0.2(3) . . . . ? Cu1 N4 C1 N1 -179.5(2) 3_545 . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.982 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.099 _database_code_depnum_ccdc_archive 'CCDC 942748' ####################################################################### # # 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 #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu(\`I2-Cl)(1-tza)(1-Htza)(H2O)].1/2H2O' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C6 H10 Cl Cu N8 O5.50' _chemical_formula_sum 'C6 H10 Cl Cu N8 O5.50' _chemical_formula_weight 381.22 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' 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' 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' H H 0.0000 0.0000 '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 6.537(2) _cell_length_b 9.314(3) _cell_length_c 11.282(4) _cell_angle_alpha 108.282(3) _cell_angle_beta 99.043(4) _cell_angle_gamma 98.410(2) _cell_volume 630.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2092 _cell_measurement_theta_min 2.3548 _cell_measurement_theta_max 27.4623 _exptl_crystal_description Prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.010 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 1.990 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7599 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6171 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2854 _reflns_number_gt 2433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0522P)^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 2854 _refine_ls_number_parameters 206 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.079 _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 -0.12412(5) 0.29713(3) 0.39978(3) 0.02292(12) Uani 1 1 d . . . Cl1 Cl -0.22442(10) 0.46548(7) 0.56673(6) 0.02455(16) Uani 1 1 d . . . O1W O -0.0286(3) 0.1619(2) 0.24800(18) 0.0289(4) Uani 1 1 d D . . H1WB H 0.034(4) 0.094(3) 0.261(3) 0.043 Uiso 1 1 d D . . H1WA H -0.133(3) 0.110(3) 0.190(2) 0.065(12) Uiso 1 1 d D . . O2W O -0.6016(11) -0.0665(11) -0.0504(6) 0.117(3) Uani 0.50 1 d P . . O11 O -0.8073(4) 0.1369(3) -0.0314(2) 0.0630(7) Uani 1 1 d . . . O12 O -1.0703(3) 0.2570(3) -0.0683(2) 0.0492(6) Uani 1 1 d . . . H12C H -1.1273 0.1722 -0.1219 0.074 Uiso 1 1 calc R . . O21 O 0.4143(3) -0.0972(2) 0.61690(18) 0.0324(4) Uani 1 1 d . . . O22 O 0.7190(3) 0.0081(2) 0.75952(19) 0.0338(5) Uani 1 1 d . . . N11 N -0.5723(3) 0.3985(2) 0.15699(19) 0.0222(4) Uani 1 1 d . . . N12 N -0.3949(4) 0.4718(3) 0.1369(2) 0.0376(6) Uani 1 1 d . . . N13 N -0.2372(4) 0.4472(3) 0.2065(2) 0.0384(6) Uani 1 1 d . . . N14 N -0.3096(3) 0.3578(3) 0.27161(19) 0.0254(5) Uani 1 1 d . . . N21 N 0.3127(3) 0.1859(2) 0.6417(2) 0.0222(4) Uani 1 1 d . . . N22 N 0.1318(4) 0.1428(3) 0.6760(2) 0.0323(5) Uani 1 1 d . . . N23 N -0.0189(3) 0.1679(3) 0.6027(2) 0.0317(5) Uani 1 1 d . . . N24 N 0.0616(3) 0.2280(2) 0.51999(19) 0.0218(4) Uani 1 1 d . . . C11 C -0.5166(4) 0.3308(3) 0.2407(2) 0.0275(6) Uani 1 1 d . . . H11A H -0.6089 0.2738 0.2722 0.033 Uiso 1 1 calc R . . C12 C -0.7824(4) 0.4025(3) 0.0932(2) 0.0272(6) Uani 1 1 d . . . H12A H -0.7704 0.4820 0.0545 0.033 Uiso 1 1 calc R . . H12B H -0.8693 0.4289 0.1558 0.033 Uiso 1 1 calc R . . C13 C -0.8880(4) 0.2491(4) -0.0084(3) 0.0342(6) Uani 1 1 d . . . C21 C 0.2667(4) 0.2376(3) 0.5460(2) 0.0218(5) Uani 1 1 d . . . H21A H 0.3632 0.2743 0.5045 0.026 Uiso 1 1 calc R . . C22 C 0.5175(4) 0.1782(3) 0.7100(3) 0.0271(6) Uani 1 1 d . . . H22A H 0.5332 0.2341 0.8005 0.033 Uiso 1 1 calc R . . H22B H 0.6287 0.2299 0.6808 0.033 Uiso 1 1 calc R . . C23 C 0.5472(4) 0.0142(3) 0.6925(2) 0.0224(5) Uani 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 0.02179(19) 0.0291(2) 0.02115(18) 0.01179(14) 0.00127(13) 0.01197(14) Cl1 0.0232(3) 0.0252(3) 0.0265(3) 0.0098(2) 0.0057(2) 0.0069(3) O1W 0.0285(11) 0.0282(10) 0.0276(10) 0.0074(8) 0.0008(8) 0.0090(9) O2W 0.094(5) 0.154(8) 0.070(4) -0.010(5) -0.011(4) 0.066(5) O11 0.0625(16) 0.0444(14) 0.0587(16) 0.0043(12) -0.0293(12) 0.0150(13) O12 0.0295(11) 0.0524(14) 0.0450(13) -0.0007(11) -0.0168(9) 0.0104(10) O21 0.0275(10) 0.0256(10) 0.0383(11) 0.0096(9) -0.0038(8) 0.0031(8) O22 0.0257(10) 0.0314(10) 0.0423(11) 0.0161(9) -0.0078(8) 0.0084(8) N11 0.0181(10) 0.0281(11) 0.0207(10) 0.0115(9) 0.0002(8) 0.0039(9) N12 0.0212(12) 0.0585(17) 0.0409(14) 0.0338(13) 0.0002(10) 0.0028(11) N13 0.0201(12) 0.0623(18) 0.0428(14) 0.0359(14) 0.0010(10) 0.0061(12) N14 0.0224(11) 0.0340(12) 0.0245(11) 0.0157(10) 0.0030(9) 0.0103(10) N21 0.0161(10) 0.0258(11) 0.0270(11) 0.0132(9) 0.0000(8) 0.0071(8) N22 0.0223(12) 0.0490(15) 0.0387(13) 0.0297(12) 0.0076(10) 0.0138(11) N23 0.0215(11) 0.0446(14) 0.0403(13) 0.0288(12) 0.0060(10) 0.0109(10) N24 0.0195(10) 0.0261(11) 0.0233(10) 0.0129(9) 0.0027(8) 0.0079(9) C11 0.0227(13) 0.0347(15) 0.0309(13) 0.0192(12) 0.0040(11) 0.0084(11) C12 0.0181(12) 0.0379(15) 0.0258(12) 0.0141(12) -0.0019(10) 0.0067(11) C13 0.0280(15) 0.0441(17) 0.0268(13) 0.0142(13) -0.0054(11) 0.0039(13) C21 0.0198(12) 0.0232(12) 0.0248(12) 0.0112(10) 0.0043(10) 0.0064(10) C22 0.0184(13) 0.0247(13) 0.0345(14) 0.0098(11) -0.0062(10) 0.0067(11) C23 0.0187(12) 0.0250(13) 0.0276(12) 0.0143(11) 0.0044(10) 0.0061(10) _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 N24 1.997(2) . ? Cu1 N14 2.011(2) . ? Cu1 O1W 2.0300(19) . ? Cu1 Cl1 2.2961(8) . ? Cu1 O21 2.3949(19) 2_556 ? Cu1 Cl1 2.8204(10) 2_566 ? Cl1 Cu1 2.8204(10) 2_566 ? O1W H1WB 0.842(10) . ? O1W H1WA 0.834(10) . ? O2W O2W 1.659(15) 2_455 ? O11 C13 1.213(4) . ? O12 C13 1.299(3) . ? O12 H12C 0.8200 . ? O21 C23 1.228(3) . ? O21 Cu1 2.3949(19) 2_556 ? O22 C23 1.271(3) . ? N11 C11 1.325(3) . ? N11 N12 1.346(3) . ? N11 C12 1.458(3) . ? N12 N13 1.288(3) . ? N13 N14 1.354(3) . ? N14 C11 1.309(3) . ? N21 C21 1.324(3) . ? N21 N22 1.346(3) . ? N21 C22 1.459(3) . ? N22 N23 1.281(3) . ? N23 N24 1.362(3) . ? N24 C21 1.310(3) . ? C11 H11A 0.9300 . ? C12 C13 1.505(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C21 H21A 0.9300 . ? C22 C23 1.523(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? 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 N24 Cu1 N14 177.18(8) . . ? N24 Cu1 O1W 91.24(8) . . ? N14 Cu1 O1W 86.05(8) . . ? N24 Cu1 Cl1 91.23(7) . . ? N14 Cu1 Cl1 91.52(7) . . ? O1W Cu1 Cl1 175.71(6) . . ? N24 Cu1 O21 90.15(8) . 2_556 ? N14 Cu1 O21 89.20(8) . 2_556 ? O1W Cu1 O21 93.10(8) . 2_556 ? Cl1 Cu1 O21 90.41(5) . 2_556 ? N24 Cu1 Cl1 87.41(7) . 2_566 ? N14 Cu1 Cl1 93.32(7) . 2_566 ? O1W Cu1 Cl1 88.78(6) . 2_566 ? Cl1 Cu1 Cl1 87.82(3) . 2_566 ? O21 Cu1 Cl1 176.95(5) 2_556 2_566 ? Cu1 Cl1 Cu1 92.18(3) . 2_566 ? Cu1 O1W H1WB 116(2) . . ? Cu1 O1W H1WA 110(2) . . ? H1WB O1W H1WA 103(2) . . ? C13 O12 H12C 109.5 . . ? C23 O21 Cu1 143.93(18) . 2_556 ? C11 N11 N12 108.2(2) . . ? C11 N11 C12 130.0(2) . . ? N12 N11 C12 121.8(2) . . ? N13 N12 N11 107.0(2) . . ? N12 N13 N14 109.7(2) . . ? C11 N14 N13 106.7(2) . . ? C11 N14 Cu1 128.65(18) . . ? N13 N14 Cu1 124.53(17) . . ? C21 N21 N22 108.5(2) . . ? C21 N21 C22 130.1(2) . . ? N22 N21 C22 121.4(2) . . ? N23 N22 N21 107.1(2) . . ? N22 N23 N24 109.5(2) . . ? C21 N24 N23 106.7(2) . . ? C21 N24 Cu1 132.24(17) . . ? N23 N24 Cu1 120.88(16) . . ? N14 C11 N11 108.5(2) . . ? N14 C11 H11A 125.8 . . ? N11 C11 H11A 125.8 . . ? N11 C12 C13 111.4(2) . . ? N11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? O11 C13 O12 126.0(3) . . ? O11 C13 C12 123.4(3) . . ? O12 C13 C12 110.5(3) . . ? N24 C21 N21 108.2(2) . . ? N24 C21 H21A 125.9 . . ? N21 C21 H21A 125.9 . . ? N21 C22 C23 113.9(2) . . ? N21 C22 H22A 108.8 . . ? C23 C22 H22A 108.8 . . ? N21 C22 H22B 108.8 . . ? C23 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? O21 C23 O22 125.8(2) . . ? O21 C23 C22 120.4(2) . . ? O22 C23 C22 113.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N24 Cu1 Cl1 Cu1 87.36(7) . . . 2_566 ? N14 Cu1 Cl1 Cu1 -93.27(7) . . . 2_566 ? O1W Cu1 Cl1 Cu1 -37.7(8) . . . 2_566 ? O21 Cu1 Cl1 Cu1 177.52(5) 2_556 . . 2_566 ? Cl1 Cu1 Cl1 Cu1 0.0 2_566 . . 2_566 ? C11 N11 N12 N13 0.4(3) . . . . ? C12 N11 N12 N13 179.8(2) . . . . ? N11 N12 N13 N14 0.3(3) . . . . ? N12 N13 N14 C11 -0.9(3) . . . . ? N12 N13 N14 Cu1 -176.70(19) . . . . ? N24 Cu1 N14 C11 98.6(16) . . . . ? O1W Cu1 N14 C11 115.0(2) . . . . ? Cl1 Cu1 N14 C11 -68.6(2) . . . . ? O21 Cu1 N14 C11 21.8(2) 2_556 . . . ? Cl1 Cu1 N14 C11 -156.5(2) 2_566 . . . ? N24 Cu1 N14 N13 -86.6(16) . . . . ? O1W Cu1 N14 N13 -70.2(2) . . . . ? Cl1 Cu1 N14 N13 106.3(2) . . . . ? O21 Cu1 N14 N13 -163.3(2) 2_556 . . . ? Cl1 Cu1 N14 N13 18.4(2) 2_566 . . . ? C21 N21 N22 N23 0.1(3) . . . . ? C22 N21 N22 N23 177.5(2) . . . . ? N21 N22 N23 N24 -0.2(3) . . . . ? N22 N23 N24 C21 0.2(3) . . . . ? N22 N23 N24 Cu1 -175.23(19) . . . . ? N14 Cu1 N24 C21 76.0(17) . . . . ? O1W Cu1 N24 C21 59.7(2) . . . . ? Cl1 Cu1 N24 C21 -116.8(2) . . . . ? O21 Cu1 N24 C21 152.8(2) 2_556 . . . ? Cl1 Cu1 N24 C21 -29.1(2) 2_566 . . . ? N14 Cu1 N24 N23 -109.9(16) . . . . ? O1W Cu1 N24 N23 -126.2(2) . . . . ? Cl1 Cu1 N24 N23 57.28(19) . . . . ? O21 Cu1 N24 N23 -33.1(2) 2_556 . . . ? Cl1 Cu1 N24 N23 145.04(19) 2_566 . . . ? N13 N14 C11 N11 1.1(3) . . . . ? Cu1 N14 C11 N11 176.72(17) . . . . ? N12 N11 C11 N14 -1.0(3) . . . . ? C12 N11 C11 N14 179.7(2) . . . . ? C11 N11 C12 C13 -73.2(3) . . . . ? N12 N11 C12 C13 107.7(3) . . . . ? N11 C12 C13 O11 1.1(4) . . . . ? N11 C12 C13 O12 -176.9(2) . . . . ? N23 N24 C21 N21 -0.2(3) . . . . ? Cu1 N24 C21 N21 174.56(17) . . . . ? N22 N21 C21 N24 0.1(3) . . . . ? C22 N21 C21 N24 -177.1(2) . . . . ? C21 N21 C22 C23 -115.1(3) . . . . ? N22 N21 C22 C23 68.1(3) . . . . ? Cu1 O21 C23 O22 79.6(4) 2_556 . . . ? Cu1 O21 C23 C22 -102.2(3) 2_556 . . . ? N21 C22 C23 O21 6.6(4) . . . . ? N21 C22 C23 O22 -175.1(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 O1W H1WB O22 0.842(10) 1.997(18) 2.742(3) 147(3) 2_656 O1W H1WA O11 0.834(10) 2.36(3) 2.984(3) 132(3) 2_455 O1W H1WA O2W 0.83(2) 2.05(2) 2.835(7) 158(3) 2_455 O12 H12C O22 0.82 1.73 2.539(3) 170.6 1_354 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.495 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 942749' ####################################################################### # # 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 #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[CuCl2(1-Htza)2(H2O)].H2O' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C6 H12 Cl2 Cu N8 O6' _chemical_formula_sum 'C6 H12 Cl2 Cu N8 O6' _chemical_formula_weight 426.68 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 orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.8662(6) _cell_length_b 10.1720(6) _cell_length_c 16.6340(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1500.17(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4057 _cell_measurement_theta_min 2.3468 _cell_measurement_theta_max 27.4700 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.110 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.889 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 1.857 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8939 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn70 (4x4 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12030 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3409 _reflns_number_gt 2902 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0367P)^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 0.0020(4) _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' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack 0.040(18) _refine_ls_number_reflns 3409 _refine_ls_number_parameters 221 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.008 _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 -0.00728(3) 0.51192(3) 0.252570(17) 0.02341(7) Uani 1 1 d . . . O1W O 0.19137(19) 0.42599(16) 0.27504(10) 0.0265(4) Uani 1 1 d D . . H1WA H 0.192(2) 0.3433(7) 0.2708(14) 0.040 Uiso 1 1 d D . . H1WB H 0.2618(12) 0.4530(16) 0.2447(9) 0.040 Uiso 1 1 d D . . O2W O 0.4276(2) 0.5060(2) 0.18856(13) 0.0597(7) Uani 1 1 d D . . H2WA H 0.5064(11) 0.5386(19) 0.2094(11) 0.089 Uiso 1 1 d D . . H2WB H 0.402(2) 0.5637(13) 0.1543(9) 0.089 Uiso 1 1 d D . . O11 O 0.07447(19) 0.7639(2) 0.55540(10) 0.0425(5) Uani 1 1 d . . . O12 O -0.0870(2) 0.81961(19) 0.65129(10) 0.0396(5) Uani 1 1 d . . . H12C H -0.0191 0.8706 0.6635 0.059 Uiso 1 1 calc R . . O21 O -0.1783(2) 0.6534(2) -0.05056(12) 0.0497(6) Uani 1 1 d . . . O22 O -0.0737(2) 0.6787(2) -0.16998(11) 0.0568(7) Uani 1 1 d . . . H22C H -0.0298 0.6192 -0.1936 0.085 Uiso 1 1 calc R . . N11 N -0.1064(2) 0.5783(2) 0.49031(11) 0.0227(5) Uani 1 1 d . . . N12 N -0.0174(2) 0.4717(2) 0.49845(12) 0.0293(5) Uani 1 1 d . . . N13 N 0.0216(2) 0.4353(2) 0.42648(11) 0.0280(5) Uani 1 1 d . . . N14 N -0.0427(2) 0.51958(18) 0.37160(11) 0.0225(5) Uani 1 1 d . . . N21 N 0.0920(2) 0.5781(2) 0.01531(11) 0.0236(5) Uani 1 1 d . . . N22 N 0.1512(3) 0.4580(2) 0.02426(12) 0.0304(6) Uani 1 1 d . . . N23 N 0.1252(3) 0.4223(2) 0.09774(12) 0.0314(6) Uani 1 1 d . . . N24 N 0.0490(2) 0.52020(19) 0.13626(11) 0.0231(5) Uani 1 1 d . . . C11 C -0.1203(3) 0.6068(2) 0.41282(14) 0.0249(6) Uani 1 1 d . . . H11A H -0.1752 0.6763 0.3914 0.030 Uiso 1 1 calc R . . C12 C -0.1610(3) 0.6494(3) 0.56077(14) 0.0274(7) Uani 1 1 d . . . H12A H -0.1821 0.5877 0.6038 0.033 Uiso 1 1 calc R . . H12B H -0.2540 0.6947 0.5475 0.033 Uiso 1 1 calc R . . C13 C -0.0445(3) 0.7480(3) 0.58857(13) 0.0266(6) Uani 1 1 d . . . C21 C 0.0297(3) 0.6150(2) 0.08443(14) 0.0273(6) Uani 1 1 d . . . H21A H -0.0190 0.6944 0.0941 0.033 Uiso 1 1 calc R . . C22 C 0.0906(3) 0.6430(3) -0.06279(14) 0.0291(7) Uani 1 1 d . . . H22A H 0.1489 0.5920 -0.1010 0.035 Uiso 1 1 calc R . . H22B H 0.1365 0.7293 -0.0582 0.035 Uiso 1 1 calc R . . C23 C -0.0701(3) 0.6568(3) -0.09258(15) 0.0303(7) Uani 1 1 d . . . Cl1 Cl -0.23153(7) 0.61567(6) 0.22551(4) 0.03016(16) Uani 1 1 d . . . Cl2 Cl -0.13388(6) 0.26646(6) 0.23855(3) 0.02816(14) Uani 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 0.02273(12) 0.03030(15) 0.01720(11) 0.00030(12) 0.00049(11) 0.00512(12) O1W 0.0275(9) 0.0280(9) 0.0242(8) 0.0006(7) 0.0019(7) 0.0026(7) O2W 0.0353(11) 0.0908(16) 0.0528(13) -0.0159(13) 0.0077(10) -0.0219(12) O11 0.0244(9) 0.0602(13) 0.0429(10) -0.0074(10) 0.0093(8) -0.0120(10) O12 0.0419(11) 0.0465(12) 0.0304(10) -0.0162(8) 0.0053(8) -0.0127(10) O21 0.0291(10) 0.0851(17) 0.0349(11) 0.0041(11) 0.0021(9) -0.0042(11) O22 0.0454(12) 0.0972(17) 0.0276(10) 0.0183(11) -0.0014(9) 0.0077(12) N11 0.0238(10) 0.0257(12) 0.0184(9) -0.0011(8) 0.0001(8) 0.0013(9) N12 0.0317(11) 0.0309(12) 0.0255(10) 0.0013(9) 0.0005(9) 0.0034(11) N13 0.0331(12) 0.0263(11) 0.0246(10) 0.0018(9) 0.0016(9) 0.0063(10) N14 0.0260(9) 0.0208(11) 0.0206(9) 0.0017(8) 0.0020(8) 0.0020(9) N21 0.0251(11) 0.0285(12) 0.0173(9) 0.0000(9) 0.0017(8) 0.0003(9) N22 0.0396(12) 0.0290(12) 0.0225(10) -0.0014(9) 0.0028(9) 0.0116(10) N23 0.0425(13) 0.0281(12) 0.0236(11) -0.0013(9) 0.0022(10) 0.0083(11) N24 0.0256(10) 0.0230(12) 0.0205(10) -0.0013(8) 0.0003(8) 0.0062(9) C11 0.0296(13) 0.0224(13) 0.0228(12) 0.0015(11) 0.0000(10) 0.0017(11) C12 0.0210(12) 0.0403(16) 0.0210(12) -0.0047(11) 0.0040(10) 0.0008(12) C13 0.0234(11) 0.0368(15) 0.0195(10) -0.0010(11) -0.0038(9) -0.0027(12) C21 0.0366(14) 0.0225(13) 0.0228(12) -0.0021(10) 0.0001(11) 0.0036(12) C22 0.0302(13) 0.0382(17) 0.0189(12) 0.0061(11) -0.0011(10) 0.0010(12) C23 0.0339(14) 0.0313(16) 0.0256(13) 0.0044(12) -0.0003(11) -0.0050(12) Cl1 0.0233(3) 0.0312(3) 0.0360(3) -0.0003(3) -0.0033(2) 0.0031(3) Cl2 0.0267(3) 0.0267(3) 0.0311(3) 0.0007(3) -0.0005(2) 0.0007(2) _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 N24 1.9998(19) . ? Cu1 O1W 2.0014(17) . ? Cu1 N14 2.0062(19) . ? Cu1 Cl1 2.2955(7) . ? Cu1 Cl2 2.7475(7) . ? O11 C13 1.201(3) . ? O12 C13 1.327(3) . ? O21 C23 1.188(3) . ? O22 C23 1.307(3) . ? N11 C11 1.327(3) . ? N11 N12 1.348(3) . ? N11 C12 1.460(3) . ? N12 N13 1.300(3) . ? N13 N14 1.376(3) . ? N14 C11 1.316(3) . ? N21 C21 1.329(3) . ? N21 N22 1.338(3) . ? N21 C22 1.458(3) . ? N22 N23 1.296(3) . ? N23 N24 1.363(3) . ? N24 C21 1.304(3) . ? C12 C13 1.512(3) . ? C22 C23 1.515(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N24 Cu1 O1W 88.82(7) . . ? N24 Cu1 N14 172.84(8) . . ? O1W Cu1 N14 88.30(7) . . ? N24 Cu1 Cl1 90.40(6) . . ? O1W Cu1 Cl1 178.37(5) . . ? N14 Cu1 Cl1 92.31(6) . . ? N24 Cu1 Cl2 93.33(6) . . ? O1W Cu1 Cl2 88.77(5) . . ? N14 Cu1 Cl2 93.17(6) . . ? Cl1 Cu1 Cl2 92.71(2) . . ? C11 N11 N12 109.13(19) . . ? C11 N11 C12 129.9(2) . . ? N12 N11 C12 120.80(19) . . ? N13 N12 N11 107.00(18) . . ? N12 N13 N14 108.86(19) . . ? C11 N14 N13 106.93(18) . . ? C11 N14 Cu1 128.49(16) . . ? N13 N14 Cu1 124.45(15) . . ? C21 N21 N22 108.92(19) . . ? C21 N21 C22 129.8(2) . . ? N22 N21 C22 121.08(19) . . ? N23 N22 N21 106.91(19) . . ? N22 N23 N24 109.08(19) . . ? C21 N24 N23 107.11(19) . . ? C21 N24 Cu1 129.63(16) . . ? N23 N24 Cu1 123.20(14) . . ? N14 C11 N11 108.1(2) . . ? N11 C12 C13 110.3(2) . . ? O11 C13 O12 122.4(2) . . ? O11 C13 C12 123.3(2) . . ? O12 C13 C12 114.2(2) . . ? N24 C21 N21 108.0(2) . . ? N21 C22 C23 110.0(2) . . ? O21 C23 O22 124.4(3) . . ? O21 C23 C22 124.4(2) . . ? O22 C23 C22 111.2(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.380 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 942750' ####################################################################### # # 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_5 #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[CuCl2(1-Htza)2].H2O' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C6 H10 Cl2 Cu N8 O5' _chemical_formula_sum 'C6 H10 Cl2 Cu N8 O5' _chemical_formula_weight 408.66 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' 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 Cc _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' _cell_length_a 26.882(16) _cell_length_b 6.802(3) _cell_length_c 7.981(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.38(3) _cell_angle_gamma 90.00 _cell_volume 1419.7(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3503 _cell_measurement_theta_min 2.0707 _cell_measurement_theta_max 27.5165 _exptl_crystal_description lamellate _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.002 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.912 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 1.953 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8378 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn70 (4x4 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4818 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2250 _reflns_number_gt 2129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The SHELXTL program applies a restraint value of 2 with the polar space group Cc in 1 (H.D. Flack and D. Schwarzenbach, Acta Cryst., 1988, A44, 499-506). The other 3 geometrical restraints are involved with the distances between O1W and H1WA (0.85 Ang), O1W and H1WB (0.85 Ang), and H1WA and H1WB (1.34 Ang). ; _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^)+(0.0600P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 2250 _refine_ls_number_parameters 206 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.32958(3) -0.76424(6) 0.88691(8) 0.03117(9) Uani 1 1 d . . . Cl1 Cl 0.29329(3) -0.57270(12) 1.06125(8) 0.0324(2) Uani 1 1 d . . . Cl2 Cl 0.36556(3) -0.94121(12) 0.70132(9) 0.0336(2) Uani 1 1 d . . . O11 O 0.11907(10) -1.1864(4) 0.8343(3) 0.0362(6) Uani 1 1 d . . . H11B H 0.1101 -1.1864 0.9257 0.054 Uiso 1 1 calc R . . O12 O 0.12060(10) -1.5119(3) 0.8417(4) 0.0376(7) Uani 1 1 d . . . O21 O 0.53601(10) 0.0031(4) 0.9389(4) 0.0425(8) Uani 1 1 d . . . H21B H 0.5630 -0.0056 0.9081 0.064 Uiso 1 1 calc R . . O22 O 0.53943(10) -0.3218(4) 0.9268(4) 0.0401(7) Uani 1 1 d . . . N11 N 0.21275(11) -1.1645(4) 0.7574(4) 0.0257(7) Uani 1 1 d . . . N12 N 0.19293(13) -1.0089(5) 0.6625(4) 0.0399(9) Uani 1 1 d . . . N13 N 0.22477(13) -0.8664(5) 0.7015(5) 0.0440(9) Uani 1 1 d . . . N14 N 0.26739(10) -0.9309(4) 0.8194(4) 0.0280(7) Uani 1 1 d . . . N21 N 0.44527(12) -0.3604(4) 1.0067(4) 0.0281(7) Uani 1 1 d . . . N22 N 0.46844(14) -0.5192(5) 1.0911(5) 0.0455(10) Uani 1 1 d . . . N23 N 0.43533(12) -0.6616(5) 1.0572(6) 0.0504(11) Uani 1 1 d . . . N24 N 0.39228(11) -0.5972(4) 0.9510(4) 0.0306(8) Uani 1 1 d . . . C11 C 0.25844(12) -1.1136(5) 0.8517(5) 0.0270(8) Uani 1 1 d . . . H11A H 0.2805 -1.1952 0.9283 0.032 Uiso 1 1 calc R . . C12 C 0.18630(14) -1.3527(5) 0.7422(5) 0.0316(9) Uani 1 1 d . . . H12A H 0.2093 -1.4519 0.8041 0.038 Uiso 1 1 calc R . . H12B H 0.1770 -1.3908 0.6219 0.038 Uiso 1 1 calc R . . C13 C 0.13768(13) -1.3461(5) 0.8137(4) 0.0225(8) Uani 1 1 d . . . C21 C 0.39909(14) -0.4102(5) 0.9223(5) 0.0298(9) Uani 1 1 d . . . H21A H 0.3753 -0.3271 0.8540 0.036 Uiso 1 1 calc R . . C22 C 0.47050(14) -0.1696(6) 1.0203(5) 0.0347(10) Uani 1 1 d . . . H22A H 0.4782 -0.1276 1.1396 0.042 Uiso 1 1 calc R . . H22B H 0.4473 -0.0742 0.9536 0.042 Uiso 1 1 calc R . . C23 C 0.51875(14) -0.1724(5) 0.9582(5) 0.0265(9) Uani 1 1 d . . . O1W O 0.58417(17) -1.6440(4) 1.1368(5) 0.0534(7) Uani 1 1 d D . . H1WA H 0.6060(7) -1.554(2) 1.178(5) 0.080 Uiso 1 1 d D . . H1WB H 0.5955(14) -1.748(2) 1.194(4) 0.080 Uiso 1 1 d 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 0.01734(15) 0.02658(18) 0.0515(2) -0.01143(17) 0.01177(13) -0.00636(15) Cl1 0.0265(4) 0.0307(4) 0.0415(5) 0.0012(4) 0.0105(4) 0.0020(3) Cl2 0.0285(4) 0.0304(4) 0.0438(5) -0.0024(4) 0.0123(4) -0.0002(3) O11 0.0450(14) 0.0286(13) 0.0431(14) 0.0041(11) 0.0271(12) 0.0011(12) O12 0.0380(14) 0.0240(12) 0.0544(16) -0.0028(11) 0.0179(12) -0.0099(10) O21 0.0292(14) 0.0278(12) 0.076(2) -0.0032(13) 0.0228(14) -0.0112(11) O22 0.0376(14) 0.0371(15) 0.0526(16) 0.0039(13) 0.0250(12) 0.0012(13) N11 0.0172(13) 0.0271(15) 0.0338(15) -0.0031(11) 0.0076(11) -0.0054(11) N12 0.0226(16) 0.0417(17) 0.050(2) 0.0192(15) -0.0025(14) -0.0082(13) N13 0.0324(17) 0.0390(18) 0.059(2) 0.0183(15) 0.0084(15) -0.0057(13) N14 0.0149(13) 0.0275(15) 0.0452(18) -0.0043(12) 0.0143(12) -0.0019(11) N21 0.0213(14) 0.0286(15) 0.0343(16) 0.0018(12) 0.0061(12) -0.0075(12) N22 0.0249(18) 0.0403(18) 0.064(2) 0.0185(16) -0.0036(17) -0.0102(13) N23 0.0173(16) 0.0364(18) 0.091(3) 0.0224(18) -0.0001(17) -0.0064(13) N24 0.0204(15) 0.0253(14) 0.0448(19) -0.0027(12) 0.0045(14) -0.0039(12) C11 0.0206(16) 0.0251(17) 0.0383(19) -0.0017(14) 0.0128(15) -0.0012(13) C12 0.0306(18) 0.0203(17) 0.045(2) -0.0032(15) 0.0111(16) -0.0074(14) C13 0.0206(16) 0.0229(17) 0.0226(16) 0.0012(13) 0.0020(13) -0.0059(12) C21 0.0196(18) 0.0325(18) 0.034(2) -0.0041(15) 0.0005(15) -0.0004(15) C22 0.0208(17) 0.038(2) 0.048(2) -0.0093(17) 0.0127(17) -0.0058(16) C23 0.0229(18) 0.0248(18) 0.0292(18) 0.0018(14) 0.0008(15) -0.0093(14) O1W 0.0703(18) 0.0389(14) 0.0532(13) 0.0033(16) 0.0189(13) 0.0007(15) _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 N14 1.988(3) . ? Cu1 N24 1.998(3) . ? Cu1 Cl1 2.2833(15) . ? Cu1 Cl2 2.2893(15) . ? O11 C13 1.223(4) . ? O11 H11B 0.8200 . ? O12 C13 1.257(4) . ? O21 C23 1.303(4) . ? O21 H21B 0.8200 . ? O22 C23 1.212(5) . ? N11 C11 1.329(4) . ? N11 N12 1.339(4) . ? N11 C12 1.455(4) . ? N12 N13 1.283(5) . ? N13 N14 1.376(4) . ? N14 C11 1.303(5) . ? N21 C21 1.312(5) . ? N21 N22 1.347(4) . ? N21 C22 1.457(5) . ? N22 N23 1.301(5) . ? N23 N24 1.340(5) . ? N24 C21 1.313(5) . ? C11 H11A 0.9300 . ? C12 C13 1.543(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C21 H21A 0.9300 . ? C22 C23 1.491(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? O1W H1WA 0.857(10) . ? O1W H1WB 0.859(10) . ? 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 N14 Cu1 N24 179.08(16) . . ? N14 Cu1 Cl1 92.26(10) . . ? N24 Cu1 Cl1 88.49(10) . . ? N14 Cu1 Cl2 88.83(10) . . ? N24 Cu1 Cl2 90.39(11) . . ? Cl1 Cu1 Cl2 176.68(4) . . ? C13 O11 H11B 109.5 . . ? C23 O21 H21B 109.5 . . ? C11 N11 N12 108.0(3) . . ? C11 N11 C12 130.3(3) . . ? N12 N11 C12 121.7(3) . . ? N13 N12 N11 107.7(3) . . ? N12 N13 N14 109.2(3) . . ? C11 N14 N13 106.1(3) . . ? C11 N14 Cu1 132.3(2) . . ? N13 N14 Cu1 121.2(2) . . ? C21 N21 N22 108.8(3) . . ? C21 N21 C22 129.6(3) . . ? N22 N21 C22 121.6(3) . . ? N23 N22 N21 106.2(3) . . ? N22 N23 N24 109.7(3) . . ? C21 N24 N23 107.0(3) . . ? C21 N24 Cu1 130.5(2) . . ? N23 N24 Cu1 122.0(2) . . ? N14 C11 N11 109.0(3) . . ? N14 C11 H11A 125.5 . . ? N11 C11 H11A 125.5 . . ? N11 C12 C13 112.5(3) . . ? N11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? O11 C13 O12 126.6(4) . . ? O11 C13 C12 118.9(3) . . ? O12 C13 C12 114.5(3) . . ? N21 C21 N24 108.3(3) . . ? N21 C21 H21A 125.8 . . ? N24 C21 H21A 125.8 . . ? N21 C22 C23 112.9(3) . . ? N21 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? N21 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? O22 C23 O21 123.4(4) . . ? O22 C23 C22 123.7(3) . . ? O21 C23 C22 112.9(3) . . ? H1WA O1W H1WB 105(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N11 N12 N13 -1.9(4) . . . . ? C12 N11 N12 N13 -179.1(3) . . . . ? N11 N12 N13 N14 2.4(5) . . . . ? N12 N13 N14 C11 -2.1(4) . . . . ? N12 N13 N14 Cu1 171.2(3) . . . . ? N24 Cu1 N14 C11 103(8) . . . . ? Cl1 Cu1 N14 C11 -111.7(3) . . . . ? Cl2 Cu1 N14 C11 71.5(3) . . . . ? N24 Cu1 N14 N13 -68(9) . . . . ? Cl1 Cu1 N14 N13 77.1(3) . . . . ? Cl2 Cu1 N14 N13 -99.8(3) . . . . ? C21 N21 N22 N23 -0.7(5) . . . . ? C22 N21 N22 N23 177.6(4) . . . . ? N21 N22 N23 N24 1.2(5) . . . . ? N22 N23 N24 C21 -1.2(5) . . . . ? N22 N23 N24 Cu1 -173.8(3) . . . . ? N14 Cu1 N24 C21 81(9) . . . . ? Cl1 Cu1 N24 C21 -64.0(4) . . . . ? Cl2 Cu1 N24 C21 112.9(4) . . . . ? N14 Cu1 N24 N23 -108(8) . . . . ? Cl1 Cu1 N24 N23 106.7(3) . . . . ? Cl2 Cu1 N24 N23 -76.5(3) . . . . ? N13 N14 C11 N11 0.8(4) . . . . ? Cu1 N14 C11 N11 -171.4(3) . . . . ? N12 N11 C11 N14 0.6(4) . . . . ? C12 N11 C11 N14 177.4(3) . . . . ? C11 N11 C12 C13 114.0(4) . . . . ? N12 N11 C12 C13 -69.5(4) . . . . ? N11 C12 C13 O11 17.8(4) . . . . ? N11 C12 C13 O12 -163.7(3) . . . . ? N22 N21 C21 N24 0.0(5) . . . . ? C22 N21 C21 N24 -178.2(4) . . . . ? N23 N24 C21 N21 0.7(5) . . . . ? Cu1 N24 C21 N21 172.4(3) . . . . ? C21 N21 C22 C23 -121.4(4) . . . . ? N22 N21 C22 C23 60.6(5) . . . . ? N21 C22 C23 O22 -11.5(5) . . . . ? N21 C22 C23 O21 167.5(3) . . . . ? 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 O11 H11B O1W 0.82 1.99 2.800(6) 170.9 3_455 O21 H21B O12 0.82 1.75 2.569(3) 177.3 3_565 O1W H1WA O11 0.857(10) 2.04(2) 2.780(4) 144(3) 4_525 O1W H1WB O12 0.859(10) 2.035(11) 2.893(4) 176(4) 4_515 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.286 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 942751'