# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Datta, Dipankar' 'Chowdhuri, S.' 'Drew, Michael G. B.' 'Naskar, Jnan P.' _publ_contact_author_name 'Dr Dipankar Datta' _publ_contact_author_address ; Department of Inorganic Chemistry Indian Association for the Cultivation of Science Calcutta 700 032 INDIA ; _publ_contact_author_email 'ICDD@MAHENDRA.IACS.RES.IN' _publ_section_title ; Chemistry of copper(I)-water bond. Some new observations ; _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands Walker, N. and Stuart, D., Acta Crystl 1983 A39 158. ; data_3a _database_code_CSD 174164 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H28 Cl Cu N4 O4' _chemical_formula_weight 727.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.052(14) _cell_length_b 11.696(14) _cell_length_c 14.049(17) _cell_angle_alpha 78.445(10) _cell_angle_beta 74.361(10) _cell_angle_gamma 73.854(10) _cell_volume 1664(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 0.786 _exptl_absorpt_correction_type 'DIFABS(Walker and Stuart, 1983)' _exptl_absorpt_correction_T_min 0.272 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5463 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.90 _reflns_number_total 5463 _reflns_number_gt 3383 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.1744P)^2^+5.6707P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5463 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1829 _refine_ls_R_factor_gt 0.1162 _refine_ls_wR_factor_ref 0.3402 _refine_ls_wR_factor_gt 0.3027 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.95567(11) 0.62929(10) 0.68744(9) 0.0612(5) Uani 1 d . . . Cl1 Cl 1.0328(2) 0.8318(2) 0.7982(2) 0.0675(7) Uani 1 d . . . O11 O 1.0549(8) 0.7056(6) 0.7896(7) 0.088(2) Uani 1 d . . . O12 O 1.013(2) 0.8934(19) 0.7009(17) 0.125(3) Uiso 0.542(9) d P A 1 O13 O 1.137(2) 0.8431(19) 0.8277(18) 0.125(3) Uiso 0.542(9) d P A 1 O14 O 0.915(2) 0.8671(19) 0.8694(19) 0.125(3) Uiso 0.542(9) d P A 1 O15 O 0.909(2) 0.889(2) 0.793(2) 0.125(3) Uiso 0.458(9) d P A 2 O16 O 1.050(3) 0.845(2) 0.892(2) 0.125(3) Uiso 0.458(9) d P A 2 O17 O 1.127(2) 0.888(2) 0.732(2) 0.125(3) Uiso 0.458(9) d P A 2 N1A N 1.1070(7) 0.5003(7) 0.6518(6) 0.0562(18) Uani 1 d . . . C2A C 1.1912(8) 0.5075(7) 0.5636(7) 0.052(2) Uani 1 d . . . C3A C 1.3010(8) 0.4099(8) 0.5403(7) 0.054(2) Uani 1 d . . . N4A N 1.3218(8) 0.3095(7) 0.6011(6) 0.064(2) Uani 1 d . . . C5A C 1.2360(9) 0.3005(8) 0.6900(7) 0.058(2) Uani 1 d . . . C10A C 1.1293(8) 0.3960(8) 0.7196(7) 0.056(2) Uani 1 d . . . C21A C 1.1603(8) 0.6178(8) 0.4944(7) 0.056(2) Uani 1 d . . . C22A C 1.1416(10) 0.6149(10) 0.4007(8) 0.069(3) Uani 1 d . . . H22A H 1.1423 0.5420 0.3834 0.082 Uiso 1 calc R . . C23A C 1.1222(12) 0.7180(11) 0.3331(9) 0.081(3) Uani 1 d . . . H23A H 1.1113 0.7159 0.2701 0.097 Uiso 1 calc R . . C24A C 1.1197(12) 0.8235(10) 0.3630(11) 0.089(4) Uani 1 d . . . H24A H 1.1067 0.8935 0.3181 0.107 Uiso 1 calc R . . C25A C 1.1347(10) 0.8327(10) 0.4526(11) 0.082(3) Uani 1 d . . . H25A H 1.1296 0.9072 0.4694 0.099 Uiso 1 calc R . . C26A C 1.1580(9) 0.7286(8) 0.5204(8) 0.064(2) Uani 1 d . . . H26A H 1.1719 0.7324 0.5819 0.076 Uiso 1 calc R . . C31A C 1.4032(8) 0.4146(8) 0.4442(7) 0.056(2) Uani 1 d . . . C32A C 1.4684(9) 0.3082(9) 0.4029(7) 0.064(2) Uani 1 d . . . H32A H 1.4440 0.2370 0.4327 0.076 Uiso 1 calc R . . C33A C 1.5672(11) 0.3073(11) 0.3196(8) 0.075(3) Uani 1 d . . . H33A H 1.6093 0.2359 0.2933 0.090 Uiso 1 calc R . . C34A C 1.6044(11) 0.4114(12) 0.2747(8) 0.078(3) Uani 1 d . . . H34A H 1.6733 0.4100 0.2192 0.093 Uiso 1 calc R . . C35A C 1.5401(10) 0.5176(11) 0.3114(7) 0.071(3) Uani 1 d . . . H35A H 1.5640 0.5883 0.2792 0.085 Uiso 1 calc R . . C36A C 1.4395(10) 0.5209(10) 0.3963(8) 0.070(3) Uani 1 d . . . H36A H 1.3969 0.5932 0.4210 0.084 Uiso 1 calc R . . N1B N 0.7861(7) 0.7378(6) 0.7077(6) 0.0516(17) Uani 1 d . . . C2B C 0.7051(8) 0.7414(7) 0.7964(7) 0.0504(19) Uani 1 d . . . C3B C 0.5973(9) 0.8391(7) 0.8163(7) 0.054(2) Uani 1 d . . . N4B N 0.5665(7) 0.9294(6) 0.7466(6) 0.0571(18) Uani 1 d . . . C5B C 0.6440(8) 0.9235(7) 0.6515(7) 0.054(2) Uani 1 d . . . C10B C 0.7520(8) 0.8310(7) 0.6319(6) 0.051(2) Uani 1 d . . . C9B C 0.8268(9) 0.8236(9) 0.5331(7) 0.061(2) Uani 1 d . . . H9B H 0.8988 0.7605 0.5186 0.074 Uiso 1 calc R . . C8B C 0.7893(10) 0.9132(9) 0.4590(8) 0.068(3) Uani 1 d . . . H58 H 0.8371 0.9105 0.3937 0.081 Uiso 1 calc R . . C7B C 0.6828(10) 1.0061(10) 0.4799(8) 0.071(3) Uani 1 d . . . H7B H 0.6602 1.0656 0.4287 0.085 Uiso 1 calc R . . C6B C 0.6107(9) 1.0123(9) 0.5735(8) 0.067(3) Uani 1 d . . . H6B H 0.5386 1.0757 0.5865 0.080 Uiso 1 calc R . . C21B C 0.7273(8) 0.6280(7) 0.8709(7) 0.054(2) Uani 1 d . . . C22B C 0.6678(10) 0.5422(8) 0.8654(9) 0.074(3) Uani 1 d . . . H22B H 0.6207 0.5535 0.8171 0.089 Uiso 1 calc R . . C23B C 0.6792(12) 0.4366(10) 0.9342(11) 0.088(4) Uani 1 d . . . H23B H 0.6386 0.3777 0.9321 0.106 Uiso 1 calc R . . C24B C 0.7497(12) 0.4200(10) 1.0041(9) 0.080(3) Uani 1 d . . . H24B H 0.7566 0.3503 1.0497 0.096 Uiso 1 calc R . . C25B C 0.8086(11) 0.5044(9) 1.0069(8) 0.072(3) Uani 1 d . . . H25B H 0.8581 0.4917 1.0538 0.086 Uiso 1 calc R . . C26B C 0.7976(9) 0.6099(9) 0.9417(7) 0.063(2) Uani 1 d . . . H26B H 0.8377 0.6685 0.9457 0.076 Uiso 1 calc R . . C31B C 0.5061(9) 0.8470(8) 0.9165(7) 0.059(2) Uani 1 d . . . C32B C 0.3744(10) 0.8734(8) 0.9256(9) 0.073(3) Uani 1 d . . . H32B H 0.3416 0.8811 0.8696 0.088 Uiso 1 calc R . . C33B C 0.2901(13) 0.8885(10) 1.0179(13) 0.104(5) Uani 1 d . . . H33B H 0.2014 0.9041 1.0237 0.125 Uiso 1 calc R . . C34B C 0.3374(16) 0.8803(12) 1.1013(11) 0.096(4) Uani 1 d . . . H34B H 0.2805 0.8918 1.1628 0.115 Uiso 1 calc R . . C35B C 0.4646(15) 0.8560(10) 1.0935(8) 0.089(4) Uani 1 d . . . H35B H 0.4962 0.8507 1.1496 0.107 Uiso 1 calc R . . C36B C 0.5512(12) 0.8382(9) 1.0010(8) 0.077(3) Uani 1 d . . . H36B H 0.6398 0.8202 0.9966 0.092 Uiso 1 calc R . . C6A C 1.2570(10) 0.1916(9) 0.7594(9) 0.073(3) Uani 1 d . . . H6B' H 1.3277 0.1280 0.7430 0.088 Uiso 1 calc R . . C9A C 1.0441(10) 0.3842(9) 0.8119(8) 0.071(3) Uani 1 d . . . H9B' H 0.9721 0.4459 0.8300 0.085 Uiso 1 calc R . . C8A C 1.0685(11) 0.2793(9) 0.8758(8) 0.075(3) Uani 1 d . . . H8A H 1.0139 0.2726 0.9388 0.090 Uiso 1 calc R . . C7A C 1.1709(12) 0.1838(9) 0.8501(8) 0.080(3) Uani 1 d . . . H7A H 1.1818 0.1133 0.8946 0.096 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0563(7) 0.0584(7) 0.0689(8) -0.0107(5) -0.0147(5) -0.0116(5) Cl1 0.0688(15) 0.0665(14) 0.0746(17) -0.0112(11) -0.0216(12) -0.0217(11) O11 0.101(6) 0.060(4) 0.108(6) -0.011(4) -0.037(5) -0.015(4) N1A 0.052(4) 0.065(4) 0.059(5) -0.007(3) -0.018(3) -0.021(3) C2A 0.052(5) 0.053(5) 0.063(6) -0.015(4) -0.016(4) -0.022(4) C3A 0.055(5) 0.051(5) 0.066(6) -0.015(4) -0.015(4) -0.024(4) N4A 0.063(5) 0.056(4) 0.073(6) -0.013(4) -0.006(4) -0.023(4) C5A 0.060(5) 0.055(5) 0.062(6) -0.009(4) -0.014(4) -0.014(4) C10A 0.051(5) 0.053(5) 0.068(6) -0.009(4) -0.016(4) -0.015(4) C21A 0.048(5) 0.056(5) 0.075(6) -0.020(4) -0.016(4) -0.020(4) C22A 0.062(6) 0.076(6) 0.083(7) -0.022(5) -0.028(5) -0.021(5) C23A 0.093(8) 0.092(8) 0.065(7) 0.002(6) -0.024(6) -0.036(6) C24A 0.078(8) 0.067(7) 0.102(10) 0.018(6) -0.003(6) -0.020(5) C25A 0.060(6) 0.066(6) 0.127(11) -0.019(7) -0.013(6) -0.028(5) C26A 0.067(6) 0.055(5) 0.076(7) -0.015(5) -0.014(5) -0.024(4) C31A 0.048(5) 0.061(5) 0.068(6) -0.021(4) -0.014(4) -0.018(4) C32A 0.062(6) 0.073(6) 0.063(6) -0.017(5) -0.021(4) -0.016(5) C33A 0.074(7) 0.083(7) 0.064(7) -0.015(5) -0.015(5) -0.010(5) C34A 0.067(6) 0.118(9) 0.047(6) -0.013(6) -0.006(4) -0.024(6) C35A 0.069(6) 0.102(8) 0.053(6) -0.001(5) -0.015(5) -0.042(6) C36A 0.071(6) 0.080(6) 0.076(7) -0.025(5) -0.016(5) -0.036(5) N1B 0.051(4) 0.045(4) 0.065(5) -0.002(3) -0.019(3) -0.021(3) C2B 0.040(4) 0.047(4) 0.069(6) -0.010(4) -0.013(4) -0.016(3) C3B 0.054(5) 0.047(4) 0.068(6) -0.019(4) -0.016(4) -0.013(4) N4B 0.047(4) 0.052(4) 0.072(5) -0.013(4) -0.007(3) -0.015(3) C5B 0.046(5) 0.051(4) 0.070(6) -0.013(4) -0.016(4) -0.014(4) C10B 0.053(5) 0.056(5) 0.055(5) -0.007(4) -0.012(4) -0.030(4) C9B 0.061(6) 0.071(6) 0.056(6) -0.015(4) -0.011(4) -0.019(4) C8B 0.066(6) 0.076(6) 0.069(7) -0.007(5) -0.021(5) -0.026(5) C7B 0.075(7) 0.079(6) 0.056(6) 0.008(5) -0.019(5) -0.022(5) C6B 0.059(6) 0.064(5) 0.077(7) -0.002(5) -0.027(5) -0.007(4) C21B 0.043(4) 0.050(4) 0.070(6) -0.017(4) -0.007(4) -0.013(3) C22B 0.074(7) 0.055(5) 0.107(9) -0.013(5) -0.038(6) -0.016(5) C23B 0.084(8) 0.063(6) 0.119(11) 0.001(6) -0.019(7) -0.033(6) C24B 0.084(8) 0.069(6) 0.079(8) -0.002(5) -0.008(6) -0.022(6) C25B 0.081(7) 0.073(6) 0.054(6) 0.000(5) -0.017(5) -0.012(5) C26B 0.063(6) 0.068(6) 0.060(6) -0.016(5) -0.004(4) -0.023(4) C31B 0.059(6) 0.049(5) 0.073(6) -0.018(4) -0.004(4) -0.022(4) C32B 0.065(6) 0.057(5) 0.090(8) -0.004(5) -0.006(5) -0.017(4) C33B 0.074(8) 0.060(6) 0.151(14) -0.019(7) 0.035(8) -0.026(5) C34B 0.110(11) 0.087(8) 0.078(9) -0.023(7) 0.004(8) -0.019(7) C35B 0.126(12) 0.073(7) 0.053(7) -0.008(5) -0.011(6) -0.007(7) C36B 0.087(8) 0.071(6) 0.073(7) -0.023(5) -0.017(6) -0.011(5) C6A 0.071(6) 0.058(5) 0.084(8) -0.016(5) -0.008(5) -0.008(5) C9A 0.064(6) 0.061(6) 0.081(8) -0.013(5) -0.009(5) -0.011(5) C8A 0.087(7) 0.074(6) 0.054(6) -0.007(5) -0.015(5) -0.005(5) C7A 0.103(9) 0.063(6) 0.066(7) 0.000(5) -0.019(6) -0.013(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1B 1.933(7) . ? Cu1 N1A 1.942(8) . ? Cl1 O15 1.36(3) . ? Cl1 O13 1.37(2) . ? Cl1 O17 1.41(3) . ? Cl1 O14 1.43(2) . ? Cl1 O16 1.43(3) . ? Cl1 O11 1.453(8) . ? Cl1 O12 1.45(2) . ? N1A C2A 1.338(11) . ? N1A C10A 1.397(11) . ? C2A C3A 1.431(12) . ? C2A C21A 1.468(13) . ? C3A N4A 1.309(12) . ? C3A C31A 1.512(13) . ? N4A C5A 1.355(12) . ? C5A C10A 1.414(12) . ? C5A C6A 1.445(14) . ? C10A C9A 1.389(13) . ? C21A C22A 1.395(14) . ? C21A C26A 1.407(12) . ? C22A C23A 1.382(15) . ? C23A C24A 1.373(18) . ? C24A C25A 1.342(18) . ? C25A C26A 1.396(16) . ? C31A C36A 1.398(14) . ? C31A C32A 1.403(12) . ? C32A C33A 1.368(14) . ? C33A C34A 1.371(16) . ? C34A C35A 1.372(16) . ? C35A C36A 1.393(14) . ? N1B C2B 1.325(11) . ? N1B C10B 1.410(11) . ? C2B C3B 1.412(11) . ? C2B C21B 1.521(12) . ? C3B N4B 1.325(12) . ? C3B C31B 1.497(13) . ? N4B C5B 1.382(12) . ? C5B C10B 1.377(12) . ? C5B C6B 1.402(13) . ? C10B C9B 1.417(13) . ? C9B C8B 1.381(14) . ? C8B C7B 1.372(14) . ? C7B C6B 1.346(14) . ? C21B C22B 1.368(12) . ? C21B C26B 1.371(13) . ? C22B C23B 1.406(15) . ? C23B C24B 1.364(17) . ? C24B C25B 1.337(15) . ? C25B C26B 1.379(14) . ? C31B C32B 1.377(14) . ? C31B C36B 1.382(15) . ? C32B C33B 1.390(17) . ? C33B C34B 1.38(2) . ? C34B C35B 1.332(19) . ? C35B C36B 1.406(16) . ? C6A C7A 1.373(15) . ? C9A C8A 1.374(14) . ? C8A C7A 1.378(14) . ? 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 N1B Cu1 N1A 166.3(3) . . ? O15 Cl1 O17 113.9(15) . . ? O13 Cl1 O14 111.6(13) . . ? O15 Cl1 O16 107.5(15) . . ? O17 Cl1 O16 101.0(15) . . ? O15 Cl1 O11 109.7(11) . . ? O13 Cl1 O11 106.5(9) . . ? O17 Cl1 O11 113.6(11) . . ? O14 Cl1 O11 109.3(9) . . ? O16 Cl1 O11 110.6(10) . . ? O13 Cl1 O12 117.7(13) . . ? O14 Cl1 O12 107.4(13) . . ? O11 Cl1 O12 103.9(9) . . ? C2A N1A C10A 118.4(7) . . ? C2A N1A Cu1 122.1(6) . . ? C10A N1A Cu1 119.5(6) . . ? N1A C2A C3A 120.2(8) . . ? N1A C2A C21A 115.8(8) . . ? C3A C2A C21A 124.1(8) . . ? N4A C3A C2A 122.7(8) . . ? N4A C3A C31A 114.5(8) . . ? C2A C3A C31A 122.8(8) . . ? C3A N4A C5A 117.6(8) . . ? N4A C5A C10A 122.5(8) . . ? N4A C5A C6A 119.0(8) . . ? C10A C5A C6A 118.5(8) . . ? C9A C10A N1A 120.4(8) . . ? C9A C10A C5A 120.9(8) . . ? N1A C10A C5A 118.6(8) . . ? C22A C21A C26A 118.9(9) . . ? C22A C21A C2A 121.7(8) . . ? C26A C21A C2A 119.2(8) . . ? C23A C22A C21A 121.4(10) . . ? C24A C23A C22A 117.0(11) . . ? C25A C24A C23A 124.5(11) . . ? C24A C25A C26A 118.9(10) . . ? C25A C26A C21A 119.3(10) . . ? C36A C31A C32A 118.2(9) . . ? C36A C31A C3A 122.4(8) . . ? C32A C31A C3A 119.4(8) . . ? C33A C32A C31A 121.2(10) . . ? C32A C33A C34A 120.2(10) . . ? C33A C34A C35A 120.1(10) . . ? C34A C35A C36A 120.8(10) . . ? C35A C36A C31A 119.5(10) . . ? C2B N1B C10B 116.3(7) . . ? C2B N1B Cu1 122.3(6) . . ? C10B N1B Cu1 120.6(6) . . ? N1B C2B C3B 121.7(8) . . ? N1B C2B C21B 115.6(7) . . ? C3B C2B C21B 122.4(8) . . ? N4B C3B C2B 122.5(8) . . ? N4B C3B C31B 114.6(8) . . ? C2B C3B C31B 122.9(8) . . ? C3B N4B C5B 116.9(7) . . ? C10B C5B N4B 121.2(8) . . ? C10B C5B C6B 119.5(8) . . ? N4B C5B C6B 119.3(8) . . ? C5B C10B N1B 121.2(8) . . ? C5B C10B C9B 120.3(8) . . ? N1B C10B C9B 118.4(8) . . ? C8B C9B C10B 117.7(9) . . ? C7B C8B C9B 121.4(10) . . ? C6B C7B C8B 120.9(9) . . ? C7B C6B C5B 120.1(9) . . ? C22B C21B C26B 120.2(9) . . ? C22B C21B C2B 115.1(8) . . ? C26B C21B C2B 124.7(8) . . ? C21B C22B C23B 118.7(11) . . ? C24B C23B C22B 120.4(11) . . ? C25B C24B C23B 119.8(11) . . ? C24B C25B C26B 121.4(11) . . ? C21B C26B C25B 119.6(10) . . ? C32B C31B C36B 118.2(9) . . ? C32B C31B C3B 120.8(9) . . ? C36B C31B C3B 120.8(9) . . ? C31B C32B C33B 120.4(13) . . ? C34B C33B C32B 120.4(13) . . ? C35B C34B C33B 119.9(12) . . ? C34B C35B C36B 120.4(12) . . ? C31B C36B C35B 120.7(12) . . ? C7A C6A C5A 118.8(9) . . ? C8A C9A C10A 118.6(9) . . ? C9A C8A C7A 122.5(10) . . ? C6A C7A C8A 120.7(10) . . ? _refine_diff_density_max 0.840 _refine_diff_density_min -1.069 _refine_diff_density_rms 0.118 #===END data_1b _database_code_CSD 174165 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 B Cu F4 N2 O2 ' _chemical_formula_weight 468.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P22121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' 'x, -y, -z' '-x, -y+1/2, z+1/2' _cell_length_a 9.166(12) _cell_length_b 13.014(17) _cell_length_c 17.57(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2096(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.095 _exptl_absorpt_correction_type 'DIFABS(Walker and Stuart, 1983)' _exptl_absorpt_correction_T_min 0.445 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6913 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0819 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.09 _reflns_number_total 3874 _reflns_number_gt 2591 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.1491P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(4) _refine_ls_number_reflns 3874 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1221 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.2103 _refine_ls_wR_factor_gt 0.1863 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.101 _refine_ls_shift/su_mean 0.008 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.05258(9) 0.13941(6) 0.20726(5) 0.0436(3) Uani 1 d . . . C21 C -0.1870(8) 0.2840(5) 0.1447(4) 0.0403(17) Uani 1 d . . . C22 C -0.1328(10) 0.2456(6) 0.0771(5) 0.053(2) Uani 1 d . . . H22 H -0.0351 0.2538 0.0640 0.064 Uiso 1 calc R . . C23 C -0.2318(11) 0.1931(7) 0.0280(5) 0.062(2) Uani 1 d . . . H23 H -0.1985 0.1646 -0.0174 0.075 Uiso 1 calc R . . C24 C -0.3763(11) 0.1846(7) 0.0478(6) 0.068(3) Uani 1 d . . . H24 H -0.4407 0.1522 0.0146 0.081 Uiso 1 calc R . . C25 C -0.4263(9) 0.2218(6) 0.1137(6) 0.058(2) Uani 1 d . . . H25 H -0.5242 0.2141 0.1262 0.070 Uiso 1 calc R . . C26 C -0.3318(9) 0.2724(6) 0.1639(5) 0.054(2) Uani 1 d . . . H26 H -0.3666 0.2979 0.2099 0.065 Uiso 1 calc R . . C31 C -0.2340(7) 0.5014(5) 0.1831(4) 0.0388(17) Uani 1 d . . . C32 C -0.3584(9) 0.5177(6) 0.2264(5) 0.0500(19) Uani 1 d . . . H32 H -0.3627 0.4958 0.2768 0.060 Uiso 1 calc R . . C33 C -0.4779(9) 0.5681(6) 0.1928(6) 0.061(2) Uani 1 d . . . H33 H -0.5620 0.5793 0.2213 0.073 Uiso 1 calc R . . C34 C -0.4725(9) 0.6011(6) 0.1185(6) 0.055(2) Uani 1 d . . . H34 H -0.5527 0.6338 0.0969 0.067 Uiso 1 calc R . . C35 C -0.3496(13) 0.5857(7) 0.0766(5) 0.070(3) Uani 1 d . . . H35 H -0.3451 0.6087 0.0265 0.084 Uiso 1 calc R . . C36 C -0.2309(9) 0.5357(6) 0.1089(5) 0.051(2) Uani 1 d . . . H36 H -0.1475 0.5250 0.0798 0.061 Uiso 1 calc R . . C2 C -0.0828(6) 0.3406(5) 0.1955(4) 0.0331(15) Uani 1 d . . . N1 N 0.0328(6) 0.2880(4) 0.2210(3) 0.0382(13) Uani 1 d . . . C10 C 0.1356(7) 0.3424(5) 0.2632(4) 0.0402(17) Uani 1 d . . . C5 C 0.1107(7) 0.4454(4) 0.2840(4) 0.0360(15) Uani 1 d . . . N4 N -0.0134(6) 0.4964(4) 0.2586(3) 0.0364(13) Uani 1 d . . . C3 C -0.1075(7) 0.4461(5) 0.2155(4) 0.0341(14) Uani 1 d . . . C9 C 0.2608(7) 0.2914(5) 0.2877(5) 0.0467(17) Uani 1 d . . . H3 H 0.2752 0.2225 0.2759 0.056 Uiso 1 calc R . . C8 C 0.3649(8) 0.3453(7) 0.3306(5) 0.052(2) Uani 1 d . . . H4 H 0.4517 0.3137 0.3450 0.063 Uiso 1 calc R . . C7 C 0.3363(9) 0.4483(5) 0.3518(4) 0.0460(18) Uani 1 d . . . H5 H 0.4028 0.4830 0.3824 0.055 Uiso 1 calc R . . C6 C 0.2135(9) 0.4974(6) 0.3281(5) 0.0451(18) Uani 1 d . . . H6 H 0.1980 0.5658 0.3413 0.054 Uiso 1 calc R . . O100 O 0.1931(8) 0.1076(6) 0.1109(4) 0.080(2) Uani 1 d . . . B1 B 0.2007(15) -0.1847(13) 0.0840(7) 0.087(5) Uani 1 d . . . F11 F 0.0929(10) -0.1181(10) 0.0792(6) 0.167(5) Uani 1 d . . . F12 F 0.2481(10) -0.2228(6) 0.0211(4) 0.118(3) Uani 1 d . . . F13 F 0.231(2) -0.2318(16) 0.1433(7) 0.298(12) Uani 1 d . . . F14 F 0.3063(17) -0.1002(16) 0.0940(13) 0.310(12) Uani 1 d . . . O301 O 0.794(3) -0.011(3) 0.479(2) 0.114(11) Uiso 0.33 d P . . O300 O 0.803(4) 0.027(3) 0.569(2) 0.127(11) Uiso 0.33 d P . . O302 O 0.904(4) 0.065(3) 0.536(2) 0.145(13) Uiso 0.33 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0440(5) 0.0369(4) 0.0500(6) -0.0007(4) -0.0081(4) -0.0002(3) C21 0.044(4) 0.035(3) 0.042(5) 0.002(3) -0.014(3) -0.003(3) C22 0.053(5) 0.053(4) 0.053(5) 0.005(4) -0.012(4) 0.000(4) C23 0.069(6) 0.073(6) 0.045(5) 0.002(4) -0.017(4) -0.007(5) C24 0.083(6) 0.058(5) 0.062(6) 0.004(4) -0.038(5) -0.013(4) C25 0.044(4) 0.058(5) 0.074(6) -0.005(4) -0.019(4) -0.004(3) C26 0.054(5) 0.047(4) 0.063(6) -0.002(4) 0.001(4) 0.001(3) C31 0.037(4) 0.040(3) 0.040(5) -0.007(3) 0.000(3) -0.003(3) C32 0.056(5) 0.046(4) 0.048(5) 0.000(3) 0.001(4) 0.002(3) C33 0.039(5) 0.059(5) 0.084(8) 0.002(5) -0.011(4) 0.003(3) C34 0.049(5) 0.045(4) 0.072(6) 0.001(4) -0.023(4) 0.004(3) C35 0.104(8) 0.059(5) 0.048(6) 0.013(4) -0.018(6) 0.009(5) C36 0.056(5) 0.050(4) 0.047(5) 0.009(4) -0.002(4) 0.014(3) C2 0.028(3) 0.046(4) 0.025(4) -0.002(3) 0.001(2) 0.001(2) N1 0.037(3) 0.040(3) 0.038(4) -0.003(2) -0.003(3) 0.001(2) C10 0.034(4) 0.048(4) 0.039(4) -0.004(3) 0.000(3) -0.002(3) C5 0.041(3) 0.031(3) 0.036(4) 0.001(3) 0.005(3) 0.001(2) N4 0.037(3) 0.035(3) 0.037(3) -0.006(2) 0.001(2) -0.002(2) C3 0.035(3) 0.035(3) 0.033(4) 0.007(3) 0.001(3) -0.003(2) C9 0.034(4) 0.048(4) 0.057(5) 0.003(4) -0.002(4) 0.007(3) C8 0.031(4) 0.071(5) 0.055(5) 0.006(4) -0.008(3) -0.003(3) C7 0.059(4) 0.043(4) 0.037(4) -0.003(3) -0.013(4) -0.004(3) C6 0.047(4) 0.034(3) 0.054(5) -0.006(3) -0.009(3) 0.006(3) O100 0.090(5) 0.092(5) 0.057(4) 0.010(4) 0.015(4) 0.017(4) B1 0.081(8) 0.150(13) 0.031(6) -0.014(7) -0.012(5) 0.055(8) F11 0.106(6) 0.232(11) 0.162(9) -0.059(8) -0.033(6) 0.094(7) F12 0.168(8) 0.108(5) 0.077(5) -0.001(4) 0.018(5) 0.039(5) F13 0.40(2) 0.38(2) 0.112(9) 0.119(12) 0.117(12) 0.23(2) F14 0.189(14) 0.33(2) 0.41(3) -0.21(2) -0.152(16) 0.055(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.957(6) . ? Cu1 N4 1.988(6) 2_545 ? Cu1 O100 2.167(7) . ? C21 C26 1.378(12) . ? C21 C22 1.381(12) . ? C21 C2 1.501(10) . ? C22 C23 1.427(12) . ? C23 C24 1.374(15) . ? C24 C25 1.336(14) . ? C25 C26 1.400(11) . ? C31 C36 1.379(11) . ? C31 C32 1.387(10) . ? C31 C3 1.478(10) . ? C32 C33 1.407(11) . ? C33 C34 1.376(13) . ? C34 C35 1.360(14) . ? C35 C36 1.389(13) . ? C2 N1 1.339(8) . ? C2 C3 1.435(9) . ? N1 C10 1.392(8) . ? C10 C9 1.395(9) . ? C10 C5 1.408(9) . ? C5 N4 1.391(9) . ? C5 C6 1.395(10) . ? N4 C3 1.321(9) . ? N4 Cu1 1.988(6) 2 ? C9 C8 1.404(11) . ? C8 C7 1.416(11) . ? C7 C6 1.360(11) . ? B1 F13 1.239(17) . ? B1 F12 1.287(14) . ? B1 F11 1.317(14) . ? B1 F14 1.48(2) . ? 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 N1 Cu1 N4 150.6(2) . 2_545 ? N1 Cu1 O100 109.9(3) . . ? N4 Cu1 O100 99.4(3) 2_545 . ? C26 C21 C22 121.2(7) . . ? C26 C21 C2 121.4(7) . . ? C22 C21 C2 117.4(7) . . ? C21 C22 C23 117.7(8) . . ? C24 C23 C22 119.9(9) . . ? C25 C24 C23 121.4(9) . . ? C24 C25 C26 120.3(9) . . ? C21 C26 C25 119.5(8) . . ? C36 C31 C32 119.1(7) . . ? C36 C31 C3 120.4(6) . . ? C32 C31 C3 120.6(7) . . ? C31 C32 C33 118.8(8) . . ? C34 C33 C32 121.0(8) . . ? C35 C34 C33 119.9(7) . . ? C34 C35 C36 119.7(8) . . ? C31 C36 C35 121.5(8) . . ? N1 C2 C3 122.2(6) . . ? N1 C2 C21 116.8(6) . . ? C3 C2 C21 121.0(6) . . ? C2 N1 C10 116.9(6) . . ? C2 N1 Cu1 122.5(4) . . ? C10 N1 Cu1 120.4(4) . . ? N1 C10 C9 118.7(6) . . ? N1 C10 C5 120.9(6) . . ? C9 C10 C5 120.4(6) . . ? N4 C5 C6 119.9(6) . . ? N4 C5 C10 120.3(6) . . ? C6 C5 C10 119.8(6) . . ? C3 N4 C5 118.7(5) . . ? C3 N4 Cu1 121.3(5) . 2 ? C5 N4 Cu1 119.9(4) . 2 ? N4 C3 C2 120.8(6) . . ? N4 C3 C31 119.4(6) . . ? C2 C3 C31 119.7(6) . . ? C10 C9 C8 119.2(7) . . ? C9 C8 C7 119.2(7) . . ? C6 C7 C8 121.2(7) . . ? C7 C6 C5 120.0(7) . . ? F13 B1 F12 117.1(13) . . ? F13 B1 F11 123.1(13) . . ? F12 B1 F11 116.9(11) . . ? F13 B1 F14 97.1(16) . . ? F12 B1 F14 99.6(14) . . ? F11 B1 F14 90.5(13) . . ? _refine_diff_density_max 0.937 _refine_diff_density_min -0.998 _refine_diff_density_rms 0.108 #===END data_2b _database_code_CSD 174166 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 B Cu F4 N2 O' _chemical_formula_weight 326.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.08(2) _cell_length_b 9.895(14) _cell_length_c 8.700(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1298(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.722 _exptl_absorpt_correction_type 'DIFABS Walker and Stuart, (1983)' _exptl_absorpt_correction_T_min 0.256 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2611 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 26.05 _reflns_number_total 1248 _reflns_number_gt 990 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.1269P)^2^+0.8178P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.001(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(6) _refine_ls_number_reflns 1248 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.1949 _refine_ls_wR_factor_gt 0.1833 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.003 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.73333(8) 0.23546(14) 0.2496(2) 0.0559(6) Uani 1 d . . . C2 C 0.6881(7) -0.0186(13) 0.3848(13) 0.048(3) Uani 1 d . . . N1 N 0.7486(5) 0.0766(11) 0.3730(11) 0.043(2) Uani 1 d . . . C10 C 0.8248(6) 0.0653(10) 0.4647(10) 0.037(2) Uani 1 d . . . C9 C 0.8920(8) 0.1624(15) 0.4546(13) 0.060(3) Uani 1 d . . . H4 H 0.8871 0.2338 0.3855 0.071 Uiso 1 calc R . . C8 C 0.9653(8) 0.1512(14) 0.5478(15) 0.063(3) Uani 1 d . . . H5 H 1.0094 0.2168 0.5443 0.076 Uiso 1 calc R . . C7 C 0.9735(7) 0.0413(17) 0.6479(16) 0.067(3) Uani 1 d . . . H6 H 1.0249 0.0327 0.7063 0.081 Uiso 1 calc R . . C6 C 0.9094(7) -0.0522(14) 0.6620(15) 0.061(3) Uani 1 d . . . H7 H 0.9163 -0.1225 0.7319 0.073 Uiso 1 calc R . . C5 C 0.8323(7) -0.0452(10) 0.5729(10) 0.038(2) Uani 1 d . . . N4 N 0.7629(6) -0.1351(11) 0.5894(10) 0.041(2) Uani 1 d . . . C21 C 0.6090(9) -0.0101(17) 0.2828(17) 0.073(4) Uani 1 d . . . H11A H 0.6032 -0.0927 0.2257 0.088 Uiso 1 calc R . . H11B H 0.6160 0.0642 0.2129 0.088 Uiso 1 calc R . . H11C H 0.5568 0.0035 0.3441 0.088 Uiso 1 calc R . . C3 C 0.6957(6) -0.1293(12) 0.4919(12) 0.045(2) Uani 1 d . . . C31 C 0.6221(10) -0.2319(15) 0.506(2) 0.071(4) Uani 1 d . . . H12A H 0.6091 -0.2687 0.4060 0.085 Uiso 1 calc R . . H12B H 0.5700 -0.1890 0.5463 0.085 Uiso 1 calc R . . H12C H 0.6404 -0.3033 0.5733 0.085 Uiso 1 calc R . . O100 O 0.7068(8) 0.3680(15) 0.4629(13) 0.091(3) Uani 1 d . . . B1 B 0.6401(11) 0.143(3) 0.806(2) 0.087(6) Uani 1 d . . . F1 F 0.6043(8) 0.0745(15) 0.6845(16) 0.142(6) Uani 1 d . . . F2 F 0.6982(18) 0.079(2) 0.892(3) 0.236(13) Uani 1 d . . . F3 F 0.5837(8) 0.2066(18) 0.888(2) 0.163(7) Uani 1 d . . . F4 F 0.6952(17) 0.227(3) 0.740(3) 0.245(15) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0532(7) 0.0593(9) 0.0551(8) 0.0262(9) -0.0052(11) -0.0028(5) C2 0.046(6) 0.063(7) 0.036(5) 0.018(5) -0.001(5) -0.013(5) N1 0.042(4) 0.064(6) 0.022(3) 0.010(4) -0.016(3) -0.004(4) C10 0.033(5) 0.044(6) 0.034(5) 0.015(4) 0.005(4) 0.002(4) C9 0.063(7) 0.064(9) 0.051(7) 0.017(5) 0.007(6) -0.004(6) C8 0.052(6) 0.082(9) 0.056(7) 0.002(6) 0.006(6) -0.018(6) C7 0.044(7) 0.095(11) 0.063(7) 0.008(7) -0.013(6) -0.010(6) C6 0.053(7) 0.075(9) 0.055(7) 0.014(6) -0.005(6) 0.008(6) C5 0.044(5) 0.046(6) 0.025(4) 0.007(4) -0.004(4) 0.010(4) N4 0.048(5) 0.045(5) 0.030(4) 0.016(4) 0.002(4) 0.001(4) C21 0.071(7) 0.074(9) 0.075(9) 0.027(7) -0.016(7) -0.019(6) C3 0.045(5) 0.058(7) 0.031(5) 0.011(4) -0.001(5) -0.003(5) C31 0.058(7) 0.083(11) 0.072(8) 0.026(7) -0.006(7) -0.025(6) O100 0.109(8) 0.097(9) 0.067(7) 0.011(6) -0.016(6) 0.003(7) B1 0.048(8) 0.122(18) 0.090(12) -0.007(10) 0.014(8) 0.040(10) F1 0.114(8) 0.177(14) 0.136(10) -0.086(10) 0.017(7) -0.022(8) F2 0.36(3) 0.17(2) 0.183(17) -0.023(14) -0.10(2) 0.15(2) F3 0.087(7) 0.191(15) 0.212(15) -0.120(14) 0.014(9) 0.008(8) F4 0.27(2) 0.38(3) 0.089(9) 0.045(17) -0.019(17) -0.22(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.894(9) 3_654 ? Cu1 N1 1.917(10) . ? Cu1 O100 2.307(14) . ? C2 N1 1.316(15) . ? C2 C3 1.443(16) . ? C2 C21 1.488(17) . ? N1 C10 1.402(12) . ? C10 C9 1.399(17) . ? C10 C5 1.447(13) . ? C9 C8 1.375(16) . ? C8 C7 1.40(2) . ? C7 C6 1.344(18) . ? C6 C5 1.398(15) . ? C5 N4 1.381(14) . ? N4 C3 1.323(14) . ? N4 Cu1 1.894(9) 3_645 ? C3 C31 1.508(16) . ? B1 F3 1.27(2) . ? B1 F2 1.31(3) . ? B1 F4 1.31(3) . ? B1 F1 1.37(2) . ? 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 N4 Cu1 N1 164.4(4) 3_654 . ? N4 Cu1 O100 102.3(4) 3_654 . ? N1 Cu1 O100 92.1(5) . . ? N1 C2 C3 122.6(9) . . ? N1 C2 C21 118.0(10) . . ? C3 C2 C21 119.4(9) . . ? C2 N1 C10 117.8(9) . . ? C2 N1 Cu1 123.2(7) . . ? C10 N1 Cu1 118.9(7) . . ? C9 C10 N1 120.1(9) . . ? C9 C10 C5 120.2(9) . . ? N1 C10 C5 119.7(8) . . ? C8 C9 C10 119.3(11) . . ? C9 C8 C7 120.1(11) . . ? C6 C7 C8 121.9(11) . . ? C7 C6 C5 120.9(11) . . ? N4 C5 C6 122.7(9) . . ? N4 C5 C10 119.6(8) . . ? C6 C5 C10 117.6(9) . . ? C3 N4 C5 119.1(9) . . ? C3 N4 Cu1 121.6(8) . 3_645 ? C5 N4 Cu1 119.3(7) . 3_645 ? N4 C3 C2 120.5(10) . . ? N4 C3 C31 118.9(11) . . ? C2 C3 C31 120.3(10) . . ? F3 B1 F2 112(2) . . ? F3 B1 F4 111(3) . . ? F2 B1 F4 98(2) . . ? F3 B1 F1 114.3(15) . . ? F2 B1 F1 118(2) . . ? F4 B1 F1 103.0(19) . . ? _refine_diff_density_max 0.574 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.095