# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_pm163 _database_code_depnum_ccdc_archive 'CCDC 883995' #TrackingRef 'archive_Pm163.cif' _audit_creation_date 2012-05-23T20:18:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H6 Cu1 N6 O6' _chemical_formula_sum 'C7 H6 Cu N6 O6' _chemical_formula_weight 333.72 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.148(3) _cell_length_b 7.071(2) _cell_length_c 14.751(14) _cell_angle_alpha 90 _cell_angle_beta 104.23(3) _cell_angle_gamma 90 _cell_volume 1127.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.4 _cell_measurement_theta_max 18.3 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prims _exptl_crystal_colour blue _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.967 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.979 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Cylindrical absorption correction by Gaussian integration. NEEDLE absorption correction in WinGX (Farrugia, 1999). Reported Tmax/Tmin includes volume correction. ; _exptl_absorpt_correction_T_min 0.7201 _exptl_absorpt_correction_T_max 0.7285 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.024488 _diffrn_orient_matrix_ub_12 -0.117725 _diffrn_orient_matrix_ub_13 0.037396 _diffrn_orient_matrix_ub_21 0.089116 _diffrn_orient_matrix_ub_22 0.029005 _diffrn_orient_matrix_ub_23 0.004609 _diffrn_orient_matrix_ub_31 0.004334 _diffrn_orient_matrix_ub_32 0.072714 _diffrn_orient_matrix_ub_33 0.058779 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled \w scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 -3 -2 2 3 0 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetI/netI 0.0422 _diffrn_reflns_number 4600 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2216 _reflns_number_gt 1632 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0490P)^2^+0.0488P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2216 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.03 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.324 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.073 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 C3 C 1.0865(3) -0.2376(5) 0.5558(2) 0.0379(7) Uani 1 1 d . . . H3 H 1.0832 -0.3292 0.51 0.046 Uiso 1 1 calc R . . C4 C 1.1902(3) -0.1540(5) 0.6087(2) 0.0413(8) Uani 1 1 d . . . H4 H 1.2715 -0.1761 0.6063 0.05 Uiso 1 1 calc R . . C5 C 1.1491(3) -0.0279(5) 0.6677(2) 0.0367(7) Uani 1 1 d . . . H5 H 1.2006 0.0483 0.7121 0.044 Uiso 1 1 calc R . . C7 C 0.8618(3) -0.1969(4) 0.5540(2) 0.0296(6) Uani 1 1 d . . . C9 C 0.7006(3) -0.3458(5) 0.4626(2) 0.0448(8) Uani 1 1 d . . . H9 H 0.667 -0.4282 0.4139 0.054 Uiso 1 1 calc R . . C10 C 0.6220(3) -0.2596(5) 0.5080(2) 0.0406(8) Uani 1 1 d . . . H10 H 0.5375 -0.2847 0.4919 0.049 Uiso 1 1 calc R . . C11 C 0.6721(3) -0.1358(4) 0.5776(2) 0.0352(7) Uani 1 1 d . . . H11 H 0.621 -0.0744 0.6094 0.042 Uiso 1 1 calc R . . N1 N 1.0268(2) -0.0316(3) 0.65181(17) 0.0310(6) Uani 1 1 d . . . N2 N 0.9889(2) -0.1614(3) 0.58271(17) 0.0311(6) Uani 1 1 d . . . N6 N 0.7945(2) -0.1008(3) 0.60103(17) 0.0293(5) Uani 1 1 d . . . N8 N 0.8232(3) -0.3177(4) 0.48486(18) 0.0398(7) Uani 1 1 d . . . N9 N 0.6773(2) 0.3138(4) 0.65053(17) 0.0324(6) Uani 1 1 d . . . N10 N 1.0024(2) 0.4214(4) 0.7370(2) 0.0381(6) Uani 1 1 d . . . O1 O 0.74512(19) 0.2202(3) 0.71911(13) 0.0370(5) Uani 1 1 d . . . O2 O 0.59994(19) 0.4255(3) 0.66746(15) 0.0399(5) Uani 1 1 d . . . O3 O 0.6893(2) 0.2885(3) 0.57087(14) 0.0428(6) Uani 1 1 d . . . O4 O 1.00146(19) 0.2620(3) 0.77860(14) 0.0380(5) Uani 1 1 d . . . O5 O 0.9468(3) 0.4340(4) 0.65419(18) 0.0599(7) Uani 1 1 d . . . O6 O 1.0559(3) 0.5554(4) 0.7822(2) 0.0704(9) Uani 1 1 d . . . Cu1 Cu 0.88928(3) 0.08597(5) 0.69379(2) 0.02930(13) 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 C3 0.0452(19) 0.0321(17) 0.0413(18) -0.0011(14) 0.0197(15) 0.0066(15) C4 0.0329(17) 0.0403(18) 0.054(2) 0.0038(16) 0.0166(15) 0.0054(15) C5 0.0289(15) 0.0383(18) 0.0427(18) -0.0013(14) 0.0082(14) -0.0018(13) C7 0.0346(16) 0.0230(15) 0.0301(16) 0.0045(12) 0.0059(13) 0.0004(13) C9 0.052(2) 0.0331(17) 0.0414(19) -0.0066(15) -0.0036(16) -0.0060(16) C10 0.0325(16) 0.0410(18) 0.0423(18) 0.0036(15) -0.0022(14) -0.0075(15) C11 0.0301(16) 0.0373(18) 0.0368(18) 0.0055(14) 0.0056(13) -0.0021(13) N1 0.0290(13) 0.0302(13) 0.0347(14) -0.0059(11) 0.0097(11) -0.0033(11) N2 0.0330(13) 0.0267(12) 0.0353(14) -0.0019(11) 0.0114(11) 0.0017(11) N6 0.0287(12) 0.0299(13) 0.0291(12) 0.0006(11) 0.0066(10) -0.0028(11) N8 0.0453(16) 0.0326(15) 0.0378(15) -0.0050(12) 0.0034(13) -0.0005(13) N9 0.0304(13) 0.0302(14) 0.0349(15) -0.0048(11) 0.0047(11) 0.0000(11) N10 0.0312(14) 0.0367(15) 0.0468(16) -0.0059(14) 0.0105(12) -0.0028(13) O1 0.0339(11) 0.0452(13) 0.0294(11) -0.0002(10) 0.0032(9) 0.0108(10) O2 0.0345(11) 0.0398(13) 0.0427(13) -0.0080(10) 0.0043(10) 0.0106(10) O3 0.0523(14) 0.0463(14) 0.0306(12) -0.0003(10) 0.0118(11) 0.0097(11) O4 0.0371(12) 0.0340(12) 0.0401(12) -0.0010(10) 0.0039(10) -0.0039(10) O5 0.0782(19) 0.0540(16) 0.0471(16) 0.0083(13) 0.0145(14) -0.0101(14) O6 0.0645(18) 0.0386(15) 0.095(2) -0.0151(14) -0.0062(16) -0.0142(14) Cu1 0.0270(2) 0.0303(2) 0.0306(2) -0.00456(16) 0.00720(14) -0.00042(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C3 N2 1.358(4) . ? C3 C4 1.361(5) . ? C3 H3 0.93 . ? C4 C5 1.399(5) . ? C4 H4 0.93 . ? C5 N1 1.325(4) . ? C5 H5 0.93 . ? C7 N8 1.318(4) . ? C7 N6 1.328(4) . ? C7 N2 1.398(4) . ? C9 N8 1.340(4) . ? C9 C10 1.369(5) . ? C9 H9 0.93 . ? C10 C11 1.359(4) . ? C10 H10 0.93 . ? C11 N6 1.346(4) . ? C11 H11 0.93 . ? N1 N2 1.359(3) . ? N1 Cu1 1.973(2) . ? N6 Cu1 2.005(2) . ? N9 O3 1.228(3) . ? N9 O2 1.239(3) . ? N9 O1 1.287(3) . ? N10 O6 1.225(3) . ? N10 O5 1.230(4) . ? N10 O4 1.285(3) . ? O1 Cu1 1.979(2) . ? O2 Cu1 2.317(3) 2_656 ? O4 Cu1 1.977(2) . ? Cu1 O2 2.317(3) 2_646 ? 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 N2 C3 C4 106.8(3) . . ? N2 C3 H3 126.6 . . ? C4 C3 H3 126.6 . . ? C3 C4 C5 105.8(3) . . ? C3 C4 H4 127.1 . . ? C5 C4 H4 127.1 . . ? N1 C5 C4 110.9(3) . . ? N1 C5 H5 124.5 . . ? C4 C5 H5 124.5 . . ? N8 C7 N6 128.0(3) . . ? N8 C7 N2 117.7(3) . . ? N6 C7 N2 114.2(2) . . ? N8 C9 C10 123.4(3) . . ? N8 C9 H9 118.3 . . ? C10 C9 H9 118.3 . . ? C11 C10 C9 117.5(3) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? N6 C11 C10 121.0(3) . . ? N6 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C5 N1 N2 105.3(2) . . ? C5 N1 Cu1 141.3(2) . . ? N2 N1 Cu1 113.41(18) . . ? C3 N2 N1 111.3(2) . . ? C3 N2 C7 131.7(3) . . ? N1 N2 C7 117.0(2) . . ? C7 N6 C11 116.0(3) . . ? C7 N6 Cu1 115.01(19) . . ? C11 N6 Cu1 128.9(2) . . ? C7 N8 C9 113.9(3) . . ? O3 N9 O2 122.1(3) . . ? O3 N9 O1 119.7(2) . . ? O2 N9 O1 118.2(2) . . ? O6 N10 O5 122.9(3) . . ? O6 N10 O4 118.6(3) . . ? O5 N10 O4 118.4(3) . . ? N9 O1 Cu1 116.46(17) . . ? N9 O2 Cu1 127.05(18) . 2_656 ? N10 O4 Cu1 109.16(18) . . ? N1 Cu1 O4 92.54(10) . . ? N1 Cu1 O1 172.29(9) . . ? O4 Cu1 O1 89.74(9) . . ? N1 Cu1 N6 80.10(10) . . ? O4 Cu1 N6 172.52(9) . . ? O1 Cu1 N6 97.37(9) . . ? N1 Cu1 O2 101.25(10) . 2_646 ? O4 Cu1 O2 82.07(9) . 2_646 ? O1 Cu1 O2 86.35(9) . 2_646 ? N6 Cu1 O2 100.62(10) . 2_646 ? data_pm160b _database_code_depnum_ccdc_archive 'CCDC 883996' #TrackingRef 'archive_pm160.cif' _audit_creation_date 2012-05-24T20:17:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H6 Cl2 Cu1 N4' _chemical_formula_sum 'C7 H6 Cl2 Cu N4' _chemical_formula_weight 280.6 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/m 1' _symmetry_space_group_name_Hall '-P 2yb' _symmetry_Int_Tables_number 11 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.013(4) _cell_length_b 6.214(2) _cell_length_c 9.527(6) _cell_angle_alpha 90 _cell_angle_beta 116.29(4) _cell_angle_gamma 90 _cell_volume 478.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.8 _cell_measurement_theta_max 21.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.948 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 278 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.17 -1 0 0 0.17 0 1 0 0.09 0 -1 0 0.09 0 0 1 0.15 0 0 -1 0.15 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.801 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.4875 _exptl_absorpt_correction_T_max 0.6133 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.08712 _diffrn_orient_matrix_ub_12 0.03466 _diffrn_orient_matrix_ub_13 -0.10769 _diffrn_orient_matrix_ub_21 -0.019536 _diffrn_orient_matrix_ub_22 0.141911 _diffrn_orient_matrix_ub_23 0.038505 _diffrn_orient_matrix_ub_31 0.085753 _diffrn_orient_matrix_ub_32 0.067549 _diffrn_orient_matrix_ub_33 -0.025524 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled \w scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 2 4 -3 2 0 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_unetI/netI 0.0137 _diffrn_reflns_number 4164 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.96 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1028 _reflns_number_gt 908 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0409P)^2^+0.1870P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1028 _refine_ls_number_parameters 85 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0684 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.315 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.103 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 C3 C 0.8163(5) 0.25 0.6832(5) 0.0477(9) Uani 1 2 d S . . H3 H 0.9254 0.25 0.6978 0.057 Uiso 1 2 calc S . . C4 C 0.6758(5) 0.25 0.5424(4) 0.0547(10) Uani 1 2 d S . . H4 H 0.6706 0.25 0.4427 0.066 Uiso 1 2 calc S . . C5 C 0.5431(4) 0.25 0.5801(4) 0.0434(8) Uani 1 2 d S . . H5 H 0.4324 0.25 0.5071 0.052 Uiso 1 2 calc S . . C7 C 0.8506(4) 0.25 0.9609(4) 0.0316(6) Uani 1 2 d S . . C9 C 0.8363(4) 0.25 1.1903(4) 0.0410(8) Uani 1 2 d S . . H9 H 0.7771 0.25 1.2492 0.049 Uiso 1 2 calc S . . C10 C 1.0071(4) 0.25 1.2653(4) 0.0460(9) Uani 1 2 d S . . H10 H 1.0641 0.25 1.374 0.055 Uiso 1 2 calc S . . C11 C 1.0889(4) 0.25 1.1753(4) 0.0461(8) Uani 1 2 d S . . H11 H 1.2039 0.25 1.2247 0.055 Uiso 1 2 calc S . . N1 N 0.5958(3) 0.25 0.7342(3) 0.0342(6) Uani 1 2 d S . . N2 N 0.7633(3) 0.25 0.7965(3) 0.0350(6) Uani 1 2 d S . . N6 N 1.0128(3) 0.25 1.0204(4) 0.0445(7) Uani 1 2 d S . . N8 N 0.7553(3) 0.25 1.0347(3) 0.0323(6) Uani 1 2 d S . . Cl1 Cl 0.24463(10) 0.25 0.70088(10) 0.0496(2) Uani 1 2 d S . . Cl2 Cl 0.44039(10) 0.25 1.09227(9) 0.0414(2) Uani 1 2 d S . . Cu1 Cu 0.50511(4) 0.25 0.89048(4) 0.03492(16) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.055(2) 0.049(2) 0.055(2) 0 0.0392(19) 0 C4 0.072(3) 0.066(3) 0.0359(19) 0 0.034(2) 0 C5 0.048(2) 0.050(2) 0.0303(17) 0 0.0158(15) 0 C7 0.0291(15) 0.0302(15) 0.0370(17) 0 0.0161(13) 0 C9 0.0358(17) 0.051(2) 0.0349(17) 0 0.0149(15) 0 C10 0.0363(17) 0.053(2) 0.0349(18) 0 0.0035(15) 0 C11 0.0277(16) 0.052(2) 0.052(2) 0 0.0116(15) 0 N1 0.0341(13) 0.0406(15) 0.0281(13) 0 0.0139(11) 0 N2 0.0348(14) 0.0385(14) 0.0362(15) 0 0.0200(12) 0 N6 0.0285(13) 0.0505(18) 0.0542(19) 0 0.0182(13) 0 N8 0.0280(12) 0.0385(14) 0.0289(13) 0 0.0111(11) 0 Cl1 0.0287(4) 0.0765(6) 0.0358(5) 0 0.0072(3) 0 Cl2 0.0351(4) 0.0605(5) 0.0344(4) 0 0.0207(3) 0 Cu1 0.0249(2) 0.0541(3) 0.0256(2) 0 0.01105(16) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C3 N2 1.360(4) . ? C3 C4 1.378(6) . ? C3 H3 0.93 . ? C4 C5 1.392(5) . ? C4 H4 0.93 . ? C5 N1 1.328(4) . ? C5 H5 0.93 . ? C7 N6 1.313(4) . ? C7 N8 1.329(4) . ? C7 N2 1.407(4) . ? C9 N8 1.332(4) . ? C9 C10 1.380(5) . ? C9 H9 0.93 . ? C10 C11 1.357(6) . ? C10 H10 0.93 . ? C11 N6 1.323(5) . ? C11 H11 0.93 . ? N1 N2 1.356(4) . ? N1 Cu1 1.990(3) . ? N8 Cu1 2.056(3) . ? Cl1 Cu1 2.2401(17) . ? Cl2 Cu1 2.2426(15) . ? 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 N2 C3 C4 106.1(3) . . ? N2 C3 H3 126.9 . . ? C4 C3 H3 126.9 . . ? C3 C4 C5 105.9(3) . . ? C3 C4 H4 127.1 . . ? C5 C4 H4 127.1 . . ? N1 C5 C4 111.0(3) . . ? N1 C5 H5 124.5 . . ? C4 C5 H5 124.5 . . ? N6 C7 N8 128.9(3) . . ? N6 C7 N2 116.6(3) . . ? N8 C7 N2 114.5(2) . . ? N8 C9 C10 120.8(3) . . ? N8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 117.8(3) . . ? C11 C10 H10 121.1 . . ? C9 C10 H10 121.1 . . ? N6 C11 C10 123.1(3) . . ? N6 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? C5 N1 N2 105.5(3) . . ? C5 N1 Cu1 139.7(2) . . ? N2 N1 Cu1 114.80(19) . . ? N1 N2 C3 111.5(3) . . ? N1 N2 C7 116.9(2) . . ? C3 N2 C7 131.6(3) . . ? C7 N6 C11 114.2(3) . . ? C7 N8 C9 115.1(3) . . ? C7 N8 Cu1 114.9(2) . . ? C9 N8 Cu1 129.9(2) . . ? N1 Cu1 N8 78.90(11) . . ? N1 Cu1 Cl1 91.59(9) . . ? N8 Cu1 Cl1 170.49(8) . . ? N1 Cu1 Cl2 171.88(8) . . ? N8 Cu1 Cl2 92.98(9) . . ? Cl1 Cu1 Cl2 96.52(6) . . ? data_pm162 _database_code_depnum_ccdc_archive 'CCDC 883997' #TrackingRef 'archive_pm162.cif' _audit_creation_date 2012-05-23T20:00:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H16 Cu1 N10 O8' _chemical_formula_sum 'C14 H16 Cu N10 O8' _chemical_formula_weight 515.91 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.161(2) _cell_length_b 10.756(4) _cell_length_c 11.284(5) _cell_angle_alpha 90 _cell_angle_beta 93.29(4) _cell_angle_gamma 90 _cell_volume 988.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 18.2 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.41 -1 0 0 0.41 0 0 1 0.15 0 0 -1 0.15 0 2 1 0.07 0 -2 -1 0.07 0 -2 1 0.07 0 2 -1 0.07 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.174 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.7712 _exptl_absorpt_correction_T_max 0.8857 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.035671 _diffrn_orient_matrix_ub_12 0.057254 _diffrn_orient_matrix_ub_13 -0.065863 _diffrn_orient_matrix_ub_21 -0.001218 _diffrn_orient_matrix_ub_22 0.071018 _diffrn_orient_matrix_ub_23 0.056697 _diffrn_orient_matrix_ub_31 0.117377 _diffrn_orient_matrix_ub_32 0.018249 _diffrn_orient_matrix_ub_33 -0.014166 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled \w scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 5 2 -1 4 0 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_unetI/netI 0.0386 _diffrn_reflns_number 3963 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 26.13 _diffrn_reflns_theta_full 26.13 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _reflns_number_total 1944 _reflns_number_gt 1500 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0501P)^2^+0.3912P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1944 _refine_ls_number_parameters 159 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.504 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 C3 C 1.0560(4) 0.3710(3) 0.5825(3) 0.0588(9) Uani 1 1 d . . . H3 H 1.0083 0.4387 0.6185 0.071 Uiso 1 1 calc R . . C4 C 1.2027(4) 0.3697(3) 0.5309(3) 0.0571(8) Uani 1 1 d . . . H4 H 1.2757 0.4354 0.5242 0.068 Uiso 1 1 calc R . . C5 C 1.2194(4) 0.2484(3) 0.4904(3) 0.0514(8) Uani 1 1 d . . . H5 H 1.309 0.2205 0.4507 0.062 Uiso 1 1 calc R . . C7 C 0.8427(3) 0.2064(3) 0.6072(2) 0.0384(6) Uani 1 1 d . . . C9 C 0.6082(4) 0.2389(4) 0.6885(3) 0.0649(10) Uani 1 1 d . . . H9 H 0.5336 0.2912 0.7229 0.078 Uiso 1 1 calc R . . C10 C 0.5682(4) 0.1195(3) 0.6749(3) 0.0606(9) Uani 1 1 d . . . H10 H 0.4692 0.0893 0.7 0.073 Uiso 1 1 calc R . . C11 C 0.6757(4) 0.0432(3) 0.6236(3) 0.0558(8) Uani 1 1 d . . . H11 H 0.6497 -0.0404 0.613 0.067 Uiso 1 1 calc R . . N1 N 1.0938(3) 0.1776(2) 0.5147(2) 0.0414(6) Uani 1 1 d . . . N2 N 0.9919(3) 0.2534(2) 0.5713(2) 0.0420(6) Uani 1 1 d . . . N6 N 0.8188(3) 0.0863(2) 0.5878(2) 0.0390(5) Uani 1 1 d . . . N8 N 0.7477(3) 0.2877(3) 0.6561(3) 0.0598(7) Uani 1 1 d . . . N9 N 0.6177(3) 0.3018(2) 0.3521(2) 0.0452(6) Uani 1 1 d . . . O1 O 0.5122(3) 0.3825(2) 0.3495(3) 0.0807(8) Uani 1 1 d . . . O2 O 0.7583(3) 0.3303(3) 0.3316(3) 0.0945(10) Uani 1 1 d . . . O3 O 0.5840(3) 0.1920(2) 0.3718(2) 0.0640(7) Uani 1 1 d . . . O4 O 0.8716(3) 0.0524(2) 0.3267(2) 0.0542(6) Uani 1 1 d D . . Cu1 Cu 1 0 0.5 0.03399(16) Uani 1 2 d S . . H42 H 0.870(5) -0.004(3) 0.268(3) 0.078(13) Uiso 1 1 d D . . H41 H 0.789(4) 0.109(3) 0.318(3) 0.093(14) 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 C3 0.069(2) 0.0424(17) 0.065(2) -0.0079(15) 0.0005(17) 0.0019(16) C4 0.053(2) 0.0470(17) 0.071(2) -0.0011(16) 0.0079(16) -0.0133(15) C5 0.0414(16) 0.0517(18) 0.062(2) -0.0021(15) 0.0129(14) -0.0042(14) C7 0.0389(15) 0.0398(14) 0.0367(14) -0.0045(11) 0.0032(11) 0.0100(12) C9 0.052(2) 0.078(3) 0.065(2) -0.0128(19) 0.0144(17) 0.0178(19) C10 0.0431(18) 0.071(2) 0.070(2) -0.0013(18) 0.0258(16) 0.0014(17) C11 0.0468(18) 0.0509(17) 0.072(2) -0.0028(17) 0.0199(16) -0.0028(15) N1 0.0381(13) 0.0390(13) 0.0476(14) -0.0061(10) 0.0068(10) 0.0018(10) N2 0.0433(14) 0.0338(12) 0.0491(14) -0.0044(11) 0.0034(11) 0.0014(10) N6 0.0337(12) 0.0400(12) 0.0439(13) -0.0016(10) 0.0084(10) 0.0055(10) N8 0.0507(16) 0.0612(17) 0.0683(18) -0.0175(14) 0.0104(13) 0.0166(14) N9 0.0408(14) 0.0504(15) 0.0451(14) 0.0057(11) 0.0093(11) -0.0010(12) O1 0.0659(17) 0.0646(16) 0.113(2) 0.0168(15) 0.0161(15) 0.0205(14) O2 0.0577(16) 0.089(2) 0.141(3) 0.0126(19) 0.0450(17) -0.0125(15) O3 0.0580(14) 0.0487(13) 0.0861(18) 0.0133(12) 0.0111(12) -0.0037(11) O4 0.0587(14) 0.0487(13) 0.0550(14) -0.0076(11) -0.0001(11) 0.0128(11) Cu1 0.0284(2) 0.0296(2) 0.0450(3) -0.0044(2) 0.01096(17) 0.00098(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C3 C4 1.361(5) . ? C3 N2 1.371(4) . ? C3 H3 0.93 . ? C4 C5 1.392(5) . ? C4 H4 0.93 . ? C5 N1 1.318(4) . ? C5 H5 0.93 . ? C7 N8 1.311(4) . ? C7 N6 1.322(3) . ? C7 N2 1.400(4) . ? C9 N8 1.324(5) . ? C9 C10 1.332(5) . ? C9 H9 0.93 . ? C10 C11 1.354(5) . ? C10 H10 0.93 . ? C11 N6 1.341(4) . ? C11 H11 0.93 . ? N1 N2 1.352(3) . ? N1 Cu1 2.061(2) . ? N6 Cu1 2.049(2) . ? N9 O1 1.221(3) . ? N9 O2 1.223(3) . ? N9 O3 1.236(3) . ? O4 Cu1 2.237(2) . ? O4 H42 0.899(18) . ? O4 H41 0.910(18) . ? Cu1 N6 2.049(2) 3_756 ? Cu1 N1 2.061(2) 3_756 ? Cu1 O4 2.237(2) 3_756 ? 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 C4 C3 N2 107.0(3) . . ? C4 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? C3 C4 C5 104.7(3) . . ? C3 C4 H4 127.6 . . ? C5 C4 H4 127.6 . . ? N1 C5 C4 112.5(3) . . ? N1 C5 H5 123.8 . . ? C4 C5 H5 123.8 . . ? N8 C7 N6 129.5(3) . . ? N8 C7 N2 115.2(3) . . ? N6 C7 N2 115.3(2) . . ? N8 C9 C10 124.0(3) . . ? N8 C9 H9 118 . . ? C10 C9 H9 118 . . ? C9 C10 C11 118.2(3) . . ? C9 C10 H10 120.9 . . ? C11 C10 H10 120.9 . . ? N6 C11 C10 121.1(3) . . ? N6 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C5 N1 N2 104.8(2) . . ? C5 N1 Cu1 144.0(2) . . ? N2 N1 Cu1 111.20(17) . . ? N1 N2 C3 111.0(2) . . ? N1 N2 C7 119.2(2) . . ? C3 N2 C7 129.8(3) . . ? C7 N6 C11 114.2(2) . . ? C7 N6 Cu1 114.77(18) . . ? C11 N6 Cu1 130.9(2) . . ? C7 N8 C9 113.0(3) . . ? O1 N9 O2 119.0(3) . . ? O1 N9 O3 121.3(3) . . ? O2 N9 O3 119.6(3) . . ? Cu1 O4 H42 117(2) . . ? Cu1 O4 H41 125(2) . . ? H42 O4 H41 113(3) . . ? N6 Cu1 N6 180.00(11) 3_756 . ? N6 Cu1 N1 79.40(9) 3_756 3_756 ? N6 Cu1 N1 100.60(9) . 3_756 ? N6 Cu1 N1 100.60(9) 3_756 . ? N6 Cu1 N1 79.40(9) . . ? N1 Cu1 N1 180.00(5) 3_756 . ? N6 Cu1 O4 89.63(9) 3_756 3_756 ? N6 Cu1 O4 90.37(9) . 3_756 ? N1 Cu1 O4 89.43(9) 3_756 3_756 ? N1 Cu1 O4 90.57(9) . 3_756 ? N6 Cu1 O4 90.37(9) 3_756 . ? N6 Cu1 O4 89.63(9) . . ? N1 Cu1 O4 90.57(9) 3_756 . ? N1 Cu1 O4 89.43(9) . . ? O4 Cu1 O4 180.0000(10) 3_756 . ? 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 O4 H41 O2 0.910(18) 2.40(3) 3.130(4) 137(3) . O4 H41 O3 0.910(18) 2.02(3) 2.856(3) 153(4) . O4 H42 O1 0.899(18) 2.08(2) 2.900(4) 152(4) 2_645 O4 H42 O2 0.899(18) 2.32(3) 3.131(4) 150(4) 2_645 data_new _database_code_depnum_ccdc_archive 'CCDC 883998' #TrackingRef 'archive_pm167.cif' _audit_creation_date 2012-05-24T19:37:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H14 Cu1 N10 O7' _chemical_formula_sum 'C14 H14 Cu N10 O7' _chemical_formula_weight 497.89 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 20.563(3) _cell_length_b 7.157(4) _cell_length_c 18.260(3) _cell_angle_alpha 90 _cell_angle_beta 135.21(3) _cell_angle_gamma 90 _cell_volume 1893.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 11.5 _cell_measurement_theta_max 20 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 -1 0 0.3 -1 1 0 0.3 2 0 -1 0.3 -2 0 1 0.3 0 0 1 0.06 0 0 -1 0.06 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.22 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.6722 _exptl_absorpt_correction_T_max 0.9314 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.083423 _diffrn_orient_matrix_ub_12 0.084498 _diffrn_orient_matrix_ub_13 0.052672 _diffrn_orient_matrix_ub_21 0.026035 _diffrn_orient_matrix_ub_22 -0.052299 _diffrn_orient_matrix_ub_23 0.054963 _diffrn_orient_matrix_ub_31 0.128918 _diffrn_orient_matrix_ub_32 0.000264 _diffrn_orient_matrix_ub_33 -0.015636 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled \w scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -1 8 3 -6 2 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_number 4108 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.3 _diffrn_reflns_theta_max 26.98 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2063 _reflns_number_gt 1712 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0545P)^2^+1.5789P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2063 _refine_ls_number_parameters 149 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.12 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.633 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.076 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 C3 C 0.23817(18) 1.0040(4) 0.4999(2) 0.0433(6) Uani 1 1 d . . . H3 H 0.1805 1.0265 0.4744 0.052 Uiso 1 1 calc R . . C4 C 0.2626(2) 1.0282(4) 0.4480(2) 0.0452(6) Uani 1 1 d . . . H4 H 0.225 1.0702 0.3801 0.054 Uiso 1 1 calc R . . C5 C 0.35510(19) 0.9772(4) 0.5170(2) 0.0409(6) Uani 1 1 d . . . H5 H 0.3897 0.9805 0.5018 0.049 Uiso 1 1 calc R . . C7 C 0.32641(16) 0.8833(3) 0.6785(2) 0.0334(5) Uani 1 1 d . . . C9 C 0.2685(2) 0.8188(4) 0.7419(3) 0.0496(7) Uani 1 1 d . . . H9 H 0.2192 0.8157 0.7351 0.06 Uiso 1 1 calc R . . C10 C 0.3520(2) 0.7532(4) 0.8317(2) 0.0436(6) Uani 1 1 d . . . H10 H 0.3596 0.7055 0.8848 0.052 Uiso 1 1 calc R . . C11 C 0.42427(18) 0.7603(4) 0.8409(2) 0.0389(6) Uani 1 1 d . . . H11 H 0.4824 0.7193 0.9017 0.047 Uiso 1 1 calc R . . N1 N 0.38722(14) 0.9232(3) 0.60751(16) 0.0354(5) Uani 1 1 d . . . N2 N 0.31423(14) 0.9410(3) 0.59586(17) 0.0350(5) Uani 1 1 d . . . N3 N 0.53246(17) 0.2801(3) 0.6240(2) 0.0472(6) Uani 1 1 d . . . N6 N 0.41135(14) 0.8264(3) 0.76231(17) 0.0337(4) Uani 1 1 d . . . N8 N 0.25391(16) 0.8876(4) 0.6628(2) 0.0469(6) Uani 1 1 d . . . O1 O 0.5 0.5348(4) 0.75 0.0662(10) Uani 1 2 d SD . . H1 H 0.489(3) 0.464(5) 0.779(3) 0.099 Uiso 1 1 d D . . O2 O 0.46000(17) 0.3726(4) 0.5688(2) 0.0763(8) Uani 1 1 d . . . O3 O 0.58773(18) 0.2904(4) 0.72016(19) 0.0715(7) Uani 1 1 d . . . O4 O 0.54923(19) 0.1771(4) 0.5857(2) 0.0696(7) Uani 1 1 d . . . Cu1 Cu 0.5 0.82563(6) 0.75 0.03371(16) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.0340(13) 0.0401(14) 0.0448(14) 0.0011(13) 0.0241(12) 0.0038(11) C4 0.0462(15) 0.0466(16) 0.0341(13) 0.0072(12) 0.0255(12) 0.0043(12) C5 0.0445(14) 0.0435(14) 0.0388(13) 0.0013(12) 0.0309(12) -0.0037(12) C7 0.0315(12) 0.0304(11) 0.0414(13) -0.0046(10) 0.0269(11) -0.0015(10) C9 0.0458(15) 0.0616(18) 0.0600(18) -0.0088(15) 0.0441(15) -0.0074(14) C10 0.0528(16) 0.0471(14) 0.0493(16) -0.0034(14) 0.0427(15) -0.0054(13) C11 0.0400(13) 0.0408(13) 0.0419(14) -0.0001(12) 0.0311(12) 0.0004(12) N1 0.0302(10) 0.0409(12) 0.0359(11) 0.0015(9) 0.0238(9) -0.0009(9) N2 0.0295(9) 0.0375(11) 0.0372(10) 0.0013(9) 0.0234(9) 0.0023(9) N3 0.0445(13) 0.0443(14) 0.0529(15) -0.0135(11) 0.0346(13) -0.0095(11) N6 0.0342(10) 0.0354(10) 0.0394(11) -0.0005(9) 0.0289(10) 0.0002(9) N8 0.0374(12) 0.0589(14) 0.0537(14) -0.0016(12) 0.0355(12) 0.0017(11) O1 0.111(3) 0.0373(16) 0.119(3) 0 0.105(3) 0 O2 0.0550(14) 0.0706(16) 0.0807(18) -0.0055(14) 0.0402(14) 0.0134(12) O3 0.0585(14) 0.098(2) 0.0484(13) -0.0195(13) 0.0348(12) -0.0070(13) O4 0.0740(16) 0.0755(16) 0.0671(15) -0.0140(13) 0.0528(14) 0.0071(13) Cu1 0.0275(2) 0.0442(3) 0.0343(2) 0 0.0236(2) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C3 N2 1.353(3) . ? C3 C4 1.363(4) . ? C3 H3 0.93 . ? C4 C5 1.392(4) . ? C4 H4 0.93 . ? C5 N1 1.330(3) . ? C5 H5 0.93 . ? C7 N8 1.304(3) . ? C7 N6 1.329(3) . ? C7 N2 1.405(3) . ? C9 N8 1.342(4) . ? C9 C10 1.363(5) . ? C9 H9 0.93 . ? C10 C11 1.374(4) . ? C10 H10 0.93 . ? C11 N6 1.346(3) . ? C11 H11 0.93 . ? N1 N2 1.364(3) . ? N1 Cu1 2.018(2) . ? N3 O4 1.222(3) . ? N3 O2 1.242(4) . ? N3 O3 1.244(3) . ? N6 Cu1 1.989(2) . ? O1 Cu1 2.081(3) . ? O1 H1 0.873(19) . ? Cu1 N6 1.989(2) 2_656 ? Cu1 N1 2.018(2) 2_656 ? 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 N2 C3 C4 106.6(2) . . ? N2 C3 H3 126.7 . . ? C4 C3 H3 126.7 . . ? C3 C4 C5 106.2(2) . . ? C3 C4 H4 126.9 . . ? C5 C4 H4 126.9 . . ? N1 C5 C4 110.8(2) . . ? N1 C5 H5 124.6 . . ? C4 C5 H5 124.6 . . ? N8 C7 N6 128.6(3) . . ? N8 C7 N2 116.9(2) . . ? N6 C7 N2 114.5(2) . . ? N8 C9 C10 123.4(3) . . ? N8 C9 H9 118.3 . . ? C10 C9 H9 118.3 . . ? C9 C10 C11 117.6(3) . . ? C9 C10 H10 121.2 . . ? C11 C10 H10 121.2 . . ? N6 C11 C10 120.3(3) . . ? N6 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C5 N1 N2 105.0(2) . . ? C5 N1 Cu1 143.70(18) . . ? N2 N1 Cu1 111.34(16) . . ? C3 N2 N1 111.5(2) . . ? C3 N2 C7 130.6(2) . . ? N1 N2 C7 117.9(2) . . ? O4 N3 O2 121.3(3) . . ? O4 N3 O3 119.8(3) . . ? O2 N3 O3 118.8(3) . . ? C7 N6 C11 116.0(2) . . ? C7 N6 Cu1 115.59(17) . . ? C11 N6 Cu1 128.04(18) . . ? C7 N8 C9 114.0(2) . . ? Cu1 O1 H1 125(3) . . ? N6 Cu1 N6 179.68(12) . 2_656 ? N6 Cu1 N1 99.22(9) . 2_656 ? N6 Cu1 N1 80.67(9) 2_656 2_656 ? N6 Cu1 N1 80.67(9) . . ? N6 Cu1 N1 99.22(9) 2_656 . ? N1 Cu1 N1 139.49(13) 2_656 . ? N6 Cu1 O1 90.16(6) . . ? N6 Cu1 O1 90.16(6) 2_656 . ? N1 Cu1 O1 110.26(7) 2_656 . ? N1 Cu1 O1 110.26(7) . . ? # END of CIF