# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cu(pia-H) #TrackingRef '14773_web_deposit_cif_file_0_MarijanaDakovic_1350571009.3.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Cu N4 O2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C12 H14 Cu N4 O4' _chemical_formula_iupac ? _chemical_formula_weight 341.82 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.1601(2) _cell_length_b 7.6565(3) _cell_length_c 9.1728(3) _cell_angle_alpha 74.888(3) _cell_angle_beta 84.185(3) _cell_angle_gamma 71.767(2) _cell_volume 332.23(2) _cell_formula_units_Z 1 _cell_measurement_temperature 296 _cell_measurement_reflns_used 7361 _cell_measurement_theta_min 4.0922 _cell_measurement_theta_max 32.0965 _cell_special_details ; ; _exptl_crystal_description needle _exptl_crystal_colour violet _exptl_crystal_size_max 0.527 _exptl_crystal_size_mid 0.162 _exptl_crystal_size_min 0.081 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 175 _exptl_absorpt_coefficient_mu 1.666 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET) (compiled Apr 27 2007,17:53:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.612 _exptl_absorpt_correction_T_max 0.874 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 296 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur diffractometer with Saphire3 detector ; _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 16.3426 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 10701 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1924 # number of observed reflections (> n sig(I)) _reflns_number_gt 1730 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_cell_refinement ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_data_reduction ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002) ; _computing_publication_material ; SHELXL-97 (Sheldrick, 2008) and PLATON (Spek, 2009) ; #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.0793P)^2^+0.0009P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1924 _refine_ls_number_parameters 106 _refine_ls_number_restraints 4 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.606 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.075 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cu1 Cu Uani 0.50000 0.50000 0.50000 1.000 0.0388(1) . . O1 O Uani 1.2671(3) 0.2865(2) 0.37532(16) 1.000 0.0444(4) . . N1 N Uani 0.7242(3) 0.2683(2) 0.63845(17) 1.000 0.0344(4) . . N2 N Uani 0.8249(3) 0.4586(2) 0.37242(17) 1.000 0.0329(3) . . C1 C Uani 0.9750(3) 0.2021(2) 0.58109(18) 1.000 0.0312(4) . . C2 C Uani 1.1592(4) 0.0354(3) 0.6541(2) 1.000 0.0390(5) . . C3 C Uani 1.0792(5) -0.0655(3) 0.7904(2) 1.000 0.0485(6) . . C4 C Uani 0.8216(5) 0.0048(3) 0.8498(2) 1.000 0.0511(6) . . C5 C Uani 0.6500(4) 0.1739(3) 0.7717(2) 1.000 0.0447(5) . . C6 C Uani 1.0339(3) 0.3222(2) 0.42999(19) 1.000 0.0324(4) . . O2 O Uani 0.7375(5) 0.5482(5) 0.9429(3) 1.000 0.0904(9) . . H2 H Uiso 1.33250 -0.00820 0.61280 1.000 0.0470 calc R H3 H Uiso 1.19770 -0.17940 0.84140 1.000 0.0580 calc R H4 H Uiso 0.76490 -0.06110 0.94120 1.000 0.0610 calc R H5 H Uiso 0.47860 0.22320 0.81280 1.000 0.0540 calc R H12N H Uiso 0.894(5) 0.485(3) 0.299(2) 1.000 0.0390 . . H12O H Uiso 0.834(6) 0.455(5) 0.916(5) 1.000 0.1080 . . H22O H Uiso 0.575(4) 0.590(5) 0.936(5) 1.000 0.1080 . . 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 0.0207(2) 0.0362(2) 0.0503(2) -0.0059(1) 0.0061(1) -0.0016(1) O1 0.0267(5) 0.0466(7) 0.0485(7) -0.0073(6) 0.0088(5) -0.0013(5) N1 0.0257(6) 0.0358(7) 0.0410(7) -0.0103(5) 0.0037(5) -0.0086(5) N2 0.0206(5) 0.0322(6) 0.0367(7) -0.0023(5) 0.0054(5) -0.0019(5) C1 0.0260(6) 0.0306(7) 0.0371(7) -0.0109(6) -0.0002(5) -0.0067(5) C2 0.0312(7) 0.0358(8) 0.0458(9) -0.0111(7) -0.0041(6) -0.0021(6) C3 0.0509(11) 0.0408(9) 0.0474(10) -0.0023(8) -0.0098(8) -0.0089(8) C4 0.0550(12) 0.0560(12) 0.0414(9) -0.0014(8) 0.0004(8) -0.0242(10) C5 0.0376(9) 0.0531(10) 0.0435(9) -0.0103(8) 0.0083(7) -0.0178(8) C6 0.0249(7) 0.0316(7) 0.0387(8) -0.0100(6) 0.0031(6) -0.0056(6) O2 0.0724(15) 0.127(2) 0.0591(11) 0.0141(12) 0.0015(10) -0.0429(15) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9842(15) . . yes Cu1 N2 1.9350(16) . . yes Cu1 O1 2.8119(15) . 1_455 yes Cu1 N1 1.9842(15) . 2_666 yes Cu1 N2 1.9350(16) . 2_666 yes Cu1 O1 2.8119(15) . 2_766 yes O1 C6 1.232(2) . . yes O2 H22O 0.80(3) . . no O2 H12O 0.81(4) . . no N1 C5 1.334(2) . . yes N1 C1 1.341(2) . . yes N2 C6 1.287(2) . . yes N2 H12N 0.74(2) . . no C1 C2 1.380(3) . . no C1 C6 1.511(2) . . no C2 C3 1.386(3) . . no C3 C4 1.383(4) . . no C4 C5 1.379(3) . . no C2 H2 0.9300 . . no C3 H3 0.9300 . . no C4 H4 0.9300 . . no C5 H5 0.9300 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 82.74(6) . . . yes O1 Cu1 N1 91.73(5) 1_455 . . yes N1 Cu1 N1 180.00 . . 2_666 yes N1 Cu1 N2 97.26(6) . . 2_666 yes O1 Cu1 N1 88.27(5) 2_766 . . yes O1 Cu1 N2 93.74(6) 1_455 . . yes N1 Cu1 N2 97.26(6) 2_666 . . yes N2 Cu1 N2 180.00 . . 2_666 yes O1 Cu1 N2 86.26(6) 2_766 . . yes O1 Cu1 N1 88.27(5) 1_455 . 2_666 yes O1 Cu1 N2 86.26(6) 1_455 . 2_666 yes O1 Cu1 O1 180.00 1_455 . 2_766 yes N1 Cu1 N2 82.74(6) 2_666 . 2_666 yes O1 Cu1 N1 91.73(5) 2_766 . 2_666 yes O1 Cu1 N2 93.74(6) 2_766 . 2_666 yes Cu1 O1 C6 102.02(11) 1_655 . . yes H12O O2 H22O 126(4) . . . no Cu1 N1 C1 112.23(11) . . . yes Cu1 N1 C5 128.05(14) . . . yes C1 N1 C5 119.67(16) . . . yes Cu1 N2 C6 116.30(12) . . . yes Cu1 N2 H12N 149.2(19) . . . no C6 N2 H12N 94.5(18) . . . no N1 C1 C2 121.99(16) . . . yes N1 C1 C6 114.47(14) . . . yes C2 C1 C6 123.52(15) . . . no C1 C2 C3 118.3(2) . . . no C2 C3 C4 119.4(2) . . . no C3 C4 C5 119.09(18) . . . no N1 C5 C4 121.5(2) . . . yes N2 C6 C1 113.80(15) . . . yes O1 C6 C1 119.75(15) . . . yes O1 C6 N2 126.44(17) . . . yes C1 C2 H2 121.00 . . . no C3 C2 H2 121.00 . . . no C4 C3 H3 120.00 . . . no C2 C3 H3 120.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no N1 C5 H5 119.00 . . . no C4 C5 H5 119.00 . . . no 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 N2 Cu1 N1 C1 0.78(12) . . . . no N2 Cu1 N1 C5 -176.33(18) . . . . no O1 Cu1 N1 C1 94.34(12) 1_455 . . . no O1 Cu1 N1 C5 -82.78(17) 1_455 . . . no N2 Cu1 N1 C1 -179.22(12) 2_666 . . . no N2 Cu1 N1 C5 3.67(18) 2_666 . . . no O1 Cu1 N1 C1 -85.67(12) 2_766 . . . no O1 Cu1 N1 C5 97.22(17) 2_766 . . . no N1 Cu1 N2 C6 -4.94(13) . . . . no O1 Cu1 N2 C6 -96.21(13) 1_455 . . . no N1 Cu1 N2 C6 175.06(13) 2_666 . . . no O1 Cu1 N2 C6 83.79(13) 2_766 . . . no Cu1 O1 C6 C1 -88.34(14) 1_655 . . . no Cu1 O1 C6 N2 90.14(18) 1_655 . . . no Cu1 N1 C1 C2 -175.79(14) . . . . no Cu1 N1 C1 C6 2.81(18) . . . . no C1 N1 C5 C4 -2.7(3) . . . . no C5 N1 C1 C2 1.6(3) . . . . no C5 N1 C1 C6 -179.81(16) . . . . no Cu1 N1 C5 C4 174.26(16) . . . . no Cu1 N2 C6 C1 7.58(19) . . . . no Cu1 N2 C6 O1 -170.98(14) . . . . no N1 C1 C2 C3 0.3(3) . . . . no N1 C1 C6 O1 171.80(16) . . . . no N1 C1 C6 N2 -6.9(2) . . . . no C2 C1 C6 O1 -9.6(3) . . . . no C2 C1 C6 N2 171.72(17) . . . . no C6 C1 C2 C3 -178.19(18) . . . . no C1 C2 C3 C4 -1.1(3) . . . . no C2 C3 C4 C5 0.1(3) . . . . no C3 C4 C5 N1 1.8(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cu1 O1 2.8119(15) . 1_455 no Cu1 O1 3.9569(16) . . no Cu1 N2 3.9135(16) . 1_455 no Cu1 O1 3.9569(16) . 2_666 no Cu1 O1 2.8119(15) . 2_766 no Cu1 N2 3.9135(16) . 2_766 no O1 Cu1 3.9569(16) . . no O1 Cu1 2.8119(15) . 1_655 no O1 C2 3.245(3) . 2_856 no O1 Cu1 2.8119(15) . 1_655 no O1 O2 2.862(3) . 2_766 no O2 O2 2.811(4) . 2_767 no O2 O1 2.862(3) . 2_766 no O2 O2 2.803(4) . 2_667 no O1 H2 2.6600 . . no O1 H22O 2.88(4) . 2_766 no O1 H2 2.4500 . 2_856 no O1 H12O 2.87(4) . 2_766 no O2 H12N 2.78(2) . 2_766 no O2 H12O 2.66(4) . 2_767 no O2 H22O 2.25(3) . 2_667 no N1 N2 2.941(2) . 2_666 no N1 N2 2.591(2) . . no N1 C6 2.401(2) . . no N2 Cu1 3.9135(16) . 1_655 no N2 C6 3.042(2) . 2_766 no N2 C5 3.174(3) . 2_666 no N2 Cu1 3.9135(16) . 1_655 no N2 N1 2.591(2) . . no N2 C1 2.347(2) . . no N2 N1 2.941(2) . 2_666 no N2 C1 3.216(2) . 2_766 no N2 H5 2.7000 . 2_666 no C1 N2 3.216(2) . 2_766 no C1 C2 3.402(3) . 2_756 no C2 O1 3.245(3) . 2_856 no C2 C5 3.396(3) . 1_655 no C2 C1 3.402(3) . 2_756 no C2 C6 3.471(3) . 2_756 no C3 C6 3.364(3) . 2_756 no C3 C4 3.558(3) . 2_757 no C4 C4 3.439(3) . 2_757 no C4 C3 3.558(3) . 2_757 no C5 C2 3.396(3) . 1_455 no C6 C6 3.213(2) . 2_766 no C6 C2 3.471(3) . 2_756 no C6 C3 3.364(3) . 2_756 no H2 O1 2.4500 . 2_856 no H2 O1 2.6600 . . no H2 H2 2.5600 . 2_856 no H3 H22O 2.2500 . 1_645 no H5 N2 2.7000 . 2_666 no H5 H12N 2.5000 . 2_666 no H12N H12O 2.33(5) . 2_766 no H12N O2 2.78(2) . 2_766 no H12N H5 2.5000 . 2_666 no H12O O1 2.87(4) . 2_766 no H12O O2 2.66(4) . 2_767 no H12O H12N 2.33(5) . 2_766 no H12O H22O 2.46(5) . 2_667 no H22O H3 2.2500 . 1_465 no H22O O1 2.88(4) . 2_766 no H22O O2 2.25(3) . 2_667 no H22O H12O 2.46(5) . 2_667 no H22O H22O 1.88(5) . 2_667 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O2 H22O O2 0.80(3) 2.25(3) 2.803(4) 127(4) 2_667 yes C2 H2 O1 0.9300 2.4500 3.245(3) 144.00 2_856 yes _database_code_depnum_ccdc_archive 'CCDC 906738' ####################################################################### # # 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_cu(pia)(pia-H)(ClO4) #TrackingRef '14774_web_deposit_cif_file_2_MarijanaDakovic_1350571009.4.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H22 Cl2 Cu2 N8 O12' _chemical_formula_structural ? _chemical_formula_sum 'C24 H22 Cl2 Cu2 N8 O12' _chemical_formula_iupac ? _chemical_formula_weight 812.50 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z _cell_length_a 24.0770(5) _cell_length_b 6.5520(1) _cell_length_c 19.6808(5) _cell_angle_alpha 90 _cell_angle_beta 102.133(2) _cell_angle_gamma 90 _cell_volume 3035.34(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 1.654 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.563 _exptl_absorpt_correction_T_max 0.784 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 296 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 16.3426 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 12272 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3306 # number of observed reflections (> n sig(I)) _reflns_number_gt 2592 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_cell_refinement ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_data_reduction ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002) ; _computing_publication_material ; SHELXL-97 (Sheldrick, 2008) and PLATON (Spek, 2009) ; #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.0485P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 3306 _refine_ls_number_parameters 229 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0764 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.436 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.055 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cu1 Cu Uani 0.19722(1) 0.23380(4) 0.03991(1) 1.000 0.0303(1) . . Cl2 Cl Uani 0.07457(2) 0.32882(9) 0.13229(3) 1.000 0.0401(2) . . O1 O Uani 0.16340(6) -0.0338(2) 0.05381(7) 1.000 0.0366(5) . . O2 O Uani 0.30007(7) 0.7142(2) 0.08849(9) 1.000 0.0417(5) . . O3 O Uani 0.12542(7) 0.4121(3) 0.11570(9) 1.000 0.0568(7) . . O4 O Uani 0.08199(9) 0.1218(3) 0.14913(14) 1.000 0.0907(9) . . O5 O Uani 0.02986(8) 0.3493(4) 0.07238(11) 1.000 0.0781(8) . . O6 O Uani 0.06123(9) 0.4373(4) 0.18828(12) 1.000 0.0928(10) . . N1 N Uani 0.13127(7) 0.2437(2) -0.04089(9) 1.000 0.0292(5) . . N2 N Uani 0.08839(10) -0.2381(3) 0.01611(13) 1.000 0.0460(7) . . N3 N Uani 0.25402(7) 0.2262(2) 0.12929(9) 1.000 0.0286(5) . . N4 N Uani 0.23439(7) 0.4858(3) 0.02889(9) 1.000 0.0313(6) . . C1 C Uani 0.09683(9) 0.0800(3) -0.04419(11) 1.000 0.0337(7) . . C2 C Uani 0.04849(10) 0.0611(4) -0.09517(14) 1.000 0.0529(9) . . C3 C Uani 0.03466(12) 0.2159(4) -0.14370(16) 1.000 0.0605(10) . . C4 C Uani 0.06980(10) 0.3805(4) -0.14078(13) 1.000 0.0469(8) . . C5 C Uani 0.11777(9) 0.3904(3) -0.08853(11) 1.000 0.0348(7) . . C6 C Uani 0.11786(9) -0.0703(3) 0.01207(11) 1.000 0.0351(7) . . C7 C Uani 0.28491(8) 0.3983(3) 0.14079(10) 1.000 0.0282(6) . . C8 C Uani 0.32472(9) 0.4289(3) 0.20128(11) 1.000 0.0364(7) . . C9 C Uani 0.33308(11) 0.2746(4) 0.25072(12) 1.000 0.0441(8) . . C10 C Uani 0.30174(10) 0.0979(4) 0.23771(12) 1.000 0.0438(8) . . C11 C Uani 0.26220(9) 0.0788(3) 0.17692(11) 1.000 0.0371(7) . . C12 C Uani 0.27313(8) 0.5517(3) 0.08262(11) 1.000 0.0291(6) . . H2 H Uiso 0.02550 -0.05350 -0.09710 1.000 0.0630 calc R H3 H Uiso 0.00170 0.20770 -0.17800 1.000 0.0720 calc R H4 H Uiso 0.06150 0.48440 -0.17360 1.000 0.0560 calc R H5 H Uiso 0.14160 0.50310 -0.08640 1.000 0.0420 calc R H8 H Uiso 0.34540 0.54960 0.20880 1.000 0.0440 calc R H9 H Uiso 0.35960 0.29050 0.29220 1.000 0.0530 calc R H10 H Uiso 0.30740 -0.00780 0.27000 1.000 0.0530 calc R H11 H Uiso 0.24060 -0.03980 0.16870 1.000 0.0450 calc R H12N H Uiso 0.0558(12) -0.256(4) -0.0130(15) 1.000 0.055(9) . . H14N H Uiso 0.2274(9) 0.568(3) -0.0021(9) 1.000 0.029(6) . . H22N H Uiso 0.1023(11) -0.320(4) 0.0517(15) 1.000 0.058(8) . . 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 0.0294(2) 0.0272(2) 0.0313(2) 0.0033(1) -0.0001(1) -0.0084(1) Cl2 0.0354(3) 0.0405(3) 0.0427(3) 0.0006(2) 0.0044(2) -0.0054(2) O1 0.0354(8) 0.0319(8) 0.0405(9) 0.0047(6) 0.0038(7) -0.0101(6) O2 0.0456(9) 0.0293(8) 0.0447(9) 0.0028(6) -0.0030(8) -0.0135(7) O3 0.0425(10) 0.0702(13) 0.0570(12) -0.0026(9) 0.0089(9) -0.0170(9) O4 0.0822(15) 0.0501(13) 0.140(2) 0.0291(13) 0.0238(15) 0.0051(12) O5 0.0519(12) 0.1012(17) 0.0678(14) 0.0155(12) -0.0177(10) -0.0294(12) O6 0.0761(15) 0.124(2) 0.0852(16) -0.0377(15) 0.0326(13) -0.0028(14) N1 0.0262(9) 0.0266(9) 0.0342(10) -0.0020(7) 0.0048(7) -0.0031(7) N2 0.0455(12) 0.0383(12) 0.0517(14) 0.0041(10) 0.0047(11) -0.0192(10) N3 0.0297(9) 0.0277(9) 0.0281(9) 0.0034(7) 0.0054(7) -0.0016(7) N4 0.0354(10) 0.0245(9) 0.0301(10) 0.0069(7) -0.0022(8) -0.0057(8) C1 0.0272(11) 0.0317(11) 0.0418(13) -0.0024(9) 0.0064(9) -0.0057(9) C2 0.0374(13) 0.0480(15) 0.0655(18) 0.0023(13) -0.0066(12) -0.0169(11) C3 0.0417(15) 0.0617(18) 0.067(2) 0.0032(14) -0.0139(14) -0.0059(13) C4 0.0414(14) 0.0452(14) 0.0485(15) 0.0046(11) -0.0031(12) 0.0044(11) C5 0.0335(11) 0.0306(11) 0.0392(13) 0.0010(9) 0.0053(10) 0.0011(9) C6 0.0358(12) 0.0300(11) 0.0405(13) -0.0036(9) 0.0101(10) -0.0096(9) C7 0.0268(10) 0.0289(11) 0.0288(11) -0.0014(8) 0.0058(9) -0.0008(8) C8 0.0353(12) 0.0382(12) 0.0328(12) -0.0042(9) 0.0003(10) -0.0021(10) C9 0.0418(13) 0.0545(15) 0.0320(13) 0.0021(10) -0.0013(10) 0.0034(11) C10 0.0463(14) 0.0492(14) 0.0341(13) 0.0136(11) 0.0047(11) 0.0046(11) C11 0.0387(12) 0.0352(12) 0.0372(13) 0.0080(9) 0.0076(10) -0.0030(10) C12 0.0298(11) 0.0240(10) 0.0331(11) -0.0014(8) 0.0059(9) -0.0020(8) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9762(14) . . yes Cu1 O3 2.7680(18) . . yes Cu1 N1 1.9982(17) . . yes Cu1 N3 1.9889(17) . . yes Cu1 N4 1.9120(19) . . yes Cu1 N4 2.7482(18) . 7_555 yes Cl2 O3 1.4392(18) . . yes Cl2 O4 1.399(2) . . yes Cl2 O5 1.426(2) . . yes Cl2 O6 1.404(2) . . yes O1 C6 1.247(3) . . yes O2 C12 1.239(2) . . yes N1 C1 1.349(3) . . yes N1 C5 1.334(3) . . yes N2 C6 1.320(3) . . yes N3 C7 1.344(2) . . yes N3 C11 1.331(3) . . yes N4 C12 1.327(3) . . yes N2 H12N 0.88(3) . . no N2 H22N 0.89(3) . . no N4 H14N 0.805(19) . . no C1 C2 1.373(3) . . no C1 C6 1.489(3) . . no C2 C3 1.385(4) . . no C3 C4 1.365(4) . . no C4 C5 1.377(3) . . no C7 C12 1.505(3) . . no C7 C8 1.377(3) . . no C8 C9 1.388(3) . . no C9 C10 1.376(4) . . no C10 C11 1.369(3) . . no C2 H2 0.9300 . . no C3 H3 0.9300 . . no C4 H4 0.9300 . . no C5 H5 0.9300 . . no C8 H8 0.9300 . . no C9 H9 0.9300 . . no C10 H10 0.9300 . . no C11 H11 0.9300 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O3 88.72(6) . . . yes O1 Cu1 N1 81.80(6) . . . yes O1 Cu1 N3 94.71(6) . . . yes O1 Cu1 N4 176.50(7) . . . yes O1 Cu1 N4 84.88(6) . . 7_555 yes O3 Cu1 N1 86.18(6) . . . yes O3 Cu1 N3 85.71(6) . . . yes O3 Cu1 N4 93.26(7) . . . yes O3 Cu1 N4 173.32(6) . . 7_555 yes N1 Cu1 N3 171.24(7) . . . yes N1 Cu1 N4 101.20(7) . . . yes N1 Cu1 N4 94.77(6) . . 7_555 yes N3 Cu1 N4 82.57(7) . . . yes N3 Cu1 N4 92.91(6) . . 7_555 yes N4 Cu1 N4 93.04(7) . . 7_555 yes O3 Cl2 O4 110.43(12) . . . yes O3 Cl2 O5 107.88(12) . . . yes O3 Cl2 O6 109.39(13) . . . yes O4 Cl2 O5 108.89(15) . . . yes O4 Cl2 O6 110.11(15) . . . yes O5 Cl2 O6 110.11(13) . . . yes Cu1 O1 C6 114.19(13) . . . yes Cu1 O3 Cl2 128.29(11) . . . yes Cu1 N1 C1 112.96(13) . . . yes Cu1 N1 C5 128.17(13) . . . yes C1 N1 C5 118.85(18) . . . yes Cu1 N3 C7 112.42(12) . . . yes Cu1 N3 C11 127.83(13) . . . yes C7 N3 C11 119.70(18) . . . yes Cu1 N4 C12 117.26(14) . . . yes Cu1 N4 Cu1 86.96(7) . . 7_555 yes Cu1 N4 C12 99.75(12) 7_555 . . yes H12N N2 H22N 125(2) . . . no C6 N2 H12N 119.4(18) . . . no C6 N2 H22N 115.6(18) . . . no Cu1 N4 H14N 129.5(14) . . . no C12 N4 H14N 112.7(14) . . . no Cu1 N4 H14N 91.6(15) 7_555 . . no N1 C1 C2 121.7(2) . . . yes N1 C1 C6 112.37(18) . . . yes C2 C1 C6 126.0(2) . . . no C1 C2 C3 118.8(2) . . . no C2 C3 C4 119.5(3) . . . no C3 C4 C5 119.0(2) . . . no N1 C5 C4 122.2(2) . . . yes O1 C6 N2 122.0(2) . . . yes N2 C6 C1 119.5(2) . . . yes O1 C6 C1 118.52(18) . . . yes C8 C7 C12 123.10(18) . . . no N3 C7 C12 115.04(17) . . . yes N3 C7 C8 121.86(18) . . . yes C7 C8 C9 118.2(2) . . . no C8 C9 C10 119.3(2) . . . no C9 C10 C11 119.5(2) . . . no N3 C11 C10 121.5(2) . . . yes N4 C12 C7 112.18(17) . . . yes O2 C12 N4 128.3(2) . . . yes O2 C12 C7 119.44(19) . . . yes C1 C2 H2 121.00 . . . no C3 C2 H2 121.00 . . . no C2 C3 H3 120.00 . . . no C4 C3 H3 120.00 . . . no C3 C4 H4 121.00 . . . no C5 C4 H4 121.00 . . . no N1 C5 H5 119.00 . . . no C4 C5 H5 119.00 . . . no C7 C8 H8 121.00 . . . no C9 C8 H8 121.00 . . . no C8 C9 H9 120.00 . . . no C10 C9 H9 120.00 . . . no C9 C10 H10 120.00 . . . no C11 C10 H10 120.00 . . . no N3 C11 H11 119.00 . . . no C10 C11 H11 119.00 . . . no 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 O3 Cu1 O1 C6 82.62(14) . . . . no N1 Cu1 O1 C6 -3.71(14) . . . . no N3 Cu1 O1 C6 168.21(15) . . . . no N4 Cu1 O1 C6 -99.28(14) 7_555 . . . no O1 Cu1 O3 Cl2 -17.39(13) . . . . no N1 Cu1 O3 Cl2 64.48(13) . . . . no N3 Cu1 O3 Cl2 -112.21(13) . . . . no N4 Cu1 O3 Cl2 165.50(13) . . . . no O1 Cu1 N1 C1 2.98(14) . . . . no O1 Cu1 N1 C5 -178.67(18) . . . . no O3 Cu1 N1 C1 -86.28(14) . . . . no O3 Cu1 N1 C5 92.07(18) . . . . no N4 Cu1 N1 C1 -178.85(14) . . . . no N4 Cu1 N1 C5 -0.51(19) . . . . no N4 Cu1 N1 C1 87.10(14) 7_555 . . . no N4 Cu1 N1 C5 -94.56(18) 7_555 . . . no O1 Cu1 N3 C7 -176.49(14) . . . . no O1 Cu1 N3 C11 0.86(18) . . . . no O3 Cu1 N3 C7 -88.12(14) . . . . no O3 Cu1 N3 C11 89.22(18) . . . . no N4 Cu1 N3 C7 5.74(14) . . . . no N4 Cu1 N3 C11 -176.92(19) . . . . no N4 Cu1 N3 C7 98.42(14) 7_555 . . . no N4 Cu1 N3 C11 -84.23(18) 7_555 . . . no O3 Cu1 N4 C12 78.37(15) . . . . no O3 Cu1 N4 Cu1 177.79(5) . . . 7_555 no N1 Cu1 N4 C12 165.12(15) . . . . no N1 Cu1 N4 Cu1 -95.47(6) . . . 7_555 no N3 Cu1 N4 C12 -6.87(15) . . . . no N3 Cu1 N4 Cu1 92.54(6) . . . 7_555 no N4 Cu1 N4 C12 -99.41(15) 7_555 . . . no N4 Cu1 N4 Cu1 0.00(6) 7_555 . . 7_555 no O1 Cu1 N4 Cu1 -177.18(7) . . 7_555 7_555 no O1 Cu1 N4 C12 65.67(13) . . 7_555 7_555 no N1 Cu1 N4 Cu1 101.52(7) . . 7_555 7_555 no N1 Cu1 N4 C12 -15.63(13) . . 7_555 7_555 no N3 Cu1 N4 Cu1 -82.71(7) . . 7_555 7_555 no N3 Cu1 N4 C12 160.14(13) . . 7_555 7_555 no N4 Cu1 N4 Cu1 0.00(8) . . 7_555 7_555 no N4 Cu1 N4 C12 -117.15(14) . . 7_555 7_555 no O5 Cl2 O3 Cu1 -78.60(16) . . . . no O6 Cl2 O3 Cu1 161.63(13) . . . . no O4 Cl2 O3 Cu1 40.30(18) . . . . no Cu1 O1 C6 N2 -176.87(18) . . . . no Cu1 O1 C6 C1 3.8(2) . . . . no Cu1 N1 C1 C6 -1.9(2) . . . . no C5 N1 C1 C2 0.0(3) . . . . no Cu1 N1 C1 C2 178.52(18) . . . . no C1 N1 C5 C4 0.2(3) . . . . no C5 N1 C1 C6 179.56(18) . . . . no Cu1 N1 C5 C4 -178.06(17) . . . . no C7 N3 C11 C10 -0.2(3) . . . . no Cu1 N3 C7 C8 176.74(16) . . . . no Cu1 N3 C7 C12 -4.0(2) . . . . no C11 N3 C7 C8 -0.9(3) . . . . no C11 N3 C7 C12 178.44(18) . . . . no Cu1 N3 C11 C10 -177.41(17) . . . . no Cu1 N4 C12 C7 6.4(2) . . . . no Cu1 N4 C12 O2 92.6(2) 7_555 . . . no Cu1 N4 C12 C7 -85.26(16) 7_555 . . . no Cu1 N4 C12 O2 -175.83(18) . . . . no C6 C1 C2 C3 179.7(2) . . . . no N1 C1 C2 C3 -0.8(4) . . . . no C2 C1 C6 N2 -1.1(4) . . . . no C2 C1 C6 O1 178.3(2) . . . . no N1 C1 C6 O1 -1.2(3) . . . . no N1 C1 C6 N2 179.4(2) . . . . no C1 C2 C3 C4 1.5(4) . . . . no C2 C3 C4 C5 -1.3(4) . . . . no C3 C4 C5 N1 0.5(4) . . . . no N3 C7 C8 C9 0.9(3) . . . . no C12 C7 C8 C9 -178.4(2) . . . . no C8 C7 C12 N4 177.99(19) . . . . no N3 C7 C12 O2 -179.34(18) . . . . no N3 C7 C12 N4 -1.3(3) . . . . no C8 C7 C12 O2 -0.1(3) . . . . no C7 C8 C9 C10 0.2(3) . . . . no C8 C9 C10 C11 -1.2(4) . . . . no C9 C10 C11 N3 1.3(4) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cu1 O2 3.9948(15) . . no Cu1 O3 2.7680(18) . . no Cu1 O4 3.920(2) . . no Cu1 N2 4.016(2) . . no Cu1 O2 3.8827(15) . 7_555 no Cu1 N3 3.7656(17) . 7_555 no Cu1 N4 2.7482(18) . 7_555 no Cl2 H22N 2.95(3) . 1_565 no Cl2 H2 2.9700 . 3_555 no O1 O4 3.154(3) . . no O1 N1 2.602(2) . . no O1 N3 2.917(2) . . no O1 C1 2.355(3) . . no O1 C11 3.107(3) . . no O1 N4 3.239(2) . 7_555 no O1 C12 3.359(2) . 7_555 no O2 Cu1 3.8827(15) . 7_555 no O2 Cu1 3.9948(15) . . no O2 C11 3.199(3) . 1_565 no O2 N4 3.014(2) . 7_565 no O2 C1 3.398(3) . 7_555 no O2 C5 3.260(3) . 7_565 no O2 C6 3.218(3) . 7_555 no O3 N2 3.026(3) . 1_565 no O3 C10 3.279(3) . 6_555 no O4 C2 3.321(3) . 3_555 no O4 C6 3.254(3) . . no O4 O1 3.154(3) . . no O4 C9 3.398(3) . 6_545 no O4 Cu1 3.920(2) . . no O5 C2 3.368(4) . 3_555 no O5 N2 3.096(3) . 3_555 no O6 C3 3.227(4) . 3_565 no O6 C9 3.394(4) . 6_555 no O6 C4 3.318(3) . 3_565 no O1 H11 2.6100 . . no O2 H11 2.8400 . 1_565 no O2 H5 2.3300 . 7_565 no O2 H8 2.6200 . . no O2 H14N 2.212(18) . 7_565 no O3 H10 2.5300 . 6_555 no O3 H22N 2.16(3) . 1_565 no O4 H2 2.6100 . 3_555 no O4 H9 2.7100 . 6_545 no O5 H12N 2.23(3) . 3_555 no O5 H22N 2.86(3) . 1_565 no O5 H2 2.4600 . 3_555 no O6 H3 2.7600 . 3_565 no O6 H4 2.7600 . 4_565 no N1 O1 2.602(2) . . no N1 N4 3.022(2) . . no N1 C6 2.359(2) . . no N1 C7 3.236(3) . 7_555 no N1 C12 3.242(3) . 7_555 no N2 Cu1 4.016(2) . . no N2 O3 3.026(3) . 1_545 no N2 C5 3.358(3) . 1_545 no N2 O5 3.096(3) . 3_555 no N3 N4 2.575(2) . . no N3 O1 2.917(2) . . no N3 C5 3.435(3) . 7_555 no N3 C12 2.404(2) . . no N3 Cu1 3.7656(17) . 7_555 no N4 N1 3.022(2) . . no N4 O2 3.014(2) . 7_565 no N4 N3 2.575(2) . . no N4 C5 3.300(3) . . no N4 C7 2.352(3) . . no N4 Cu1 2.7482(18) . 7_555 no N4 O1 3.239(2) . 7_555 no N2 H2 2.7000 . . no N4 H5 2.8300 . . no C1 O2 3.398(3) . 7_555 no C1 C12 3.481(3) . 7_555 no C2 O4 3.321(3) . 3_555 no C2 O5 3.368(4) . 3_555 no C3 O6 3.227(4) . 3_565 no C4 O6 3.318(3) . 3_565 no C5 O2 3.260(3) . 7_565 no C5 N2 3.358(3) . 1_565 no C5 C7 3.338(3) . 7_555 no C5 C8 3.537(3) . 7_555 no C5 N3 3.435(3) . 7_555 no C6 C12 3.526(3) . 7_555 no C6 O4 3.254(3) . . no C6 O2 3.218(3) . 7_555 no C7 C5 3.338(3) . 7_555 no C7 N1 3.236(3) . 7_555 no C8 C5 3.537(3) . 7_555 no C9 O6 3.394(4) . 6_545 no C9 C11 3.555(3) . 6_555 no C9 O4 3.398(3) . 6_555 no C10 O3 3.279(3) . 6_545 no C11 O2 3.199(3) . 1_545 no C11 C9 3.555(3) . 6_545 no C12 C1 3.481(3) . 7_555 no C12 C6 3.526(3) . 7_555 no C2 H12N 2.62(3) . . no C5 H14N 3.05(2) . . no C9 H11 2.8900 . 6_555 no C12 H14N 2.952(19) . 7_565 no H2 N2 2.7000 . . no H2 H12N 2.1300 . . no H2 Cl2 2.9700 . 3_555 no H2 O4 2.6100 . 3_555 no H2 O5 2.4600 . 3_555 no H3 O6 2.7600 . 3_565 no H4 O6 2.7600 . 4_564 no H5 N4 2.8300 . . no H5 H14N 2.4000 . . no H5 O2 2.3300 . 7_565 no H8 O2 2.6200 . . no H9 O4 2.7100 . 6_555 no H10 O3 2.5300 . 6_545 no H11 O1 2.6100 . . no H11 O2 2.8400 . 1_545 no H11 C9 2.8900 . 6_545 no H12N C2 2.62(3) . . no H12N H2 2.1300 . . no H12N O5 2.23(3) . 3_555 no H14N C5 3.05(2) . . no H14N H5 2.4000 . . no H14N O2 2.212(18) . 7_565 no H14N C12 2.952(19) . 7_565 no H22N Cl2 2.95(3) . 1_545 no H22N O3 2.16(3) . 1_545 no H22N O5 2.86(3) . 1_545 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H12N O5 0.88(3) 2.23(3) 3.096(3) 169(3) 3_555 yes N4 H14N O2 0.805(19) 2.212(18) 3.014(2) 175(2) 7_565 yes N2 H22N O3 0.89(3) 2.16(3) 3.026(3) 163(3) 1_545 yes C2 H2 O5 0.9300 2.4600 3.368(4) 167.00 3_555 yes C5 H5 O2 0.9300 2.3300 3.260(3) 176.00 7_565 yes C10 H10 O3 0.9300 2.5300 3.279(3) 137.00 6_545 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; #===END _database_code_depnum_ccdc_archive 'CCDC 906739'