Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'B.S. Hammes' 'M.W. Carrano' 'C.J. Carrano' _publ_contact_author_name 'Dr Carl J Carano' _publ_contact_author_address ; Dr Carl J Carano Department of Chemistry & Biochemistry Southwest Texas State University San Marcos TX 78666 UNITED STATES OF AMERICA ; _publ_contact_author_email 'cc05@swt.edu' data_bsh77 _database_code_CSD 159090 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H34 B Cl N6 Ni O13' _chemical_formula_weight 683.51 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.419(2) _cell_length_b 18.220(2) _cell_length_c 18.1663(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.378(12) _cell_angle_gamma 90.00 _cell_volume 3112.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 5.37 _cell_measurement_theta_max 12.51 _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 1.459 _exptl_crystal_density_method ? _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.779 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4316 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4028 _reflns_number_observed 3085 _reflns_observed_criterion 2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or 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 w=1/[\s^2^(Fo^2^)+(0.0937P)^2^+5.9086P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4027 _refine_ls_number_parameters 429 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_obs 0.0525 _refine_ls_wR_factor_all 0.1615 _refine_ls_wR_factor_obs 0.1391 _refine_ls_goodness_of_fit_all 0.976 _refine_ls_goodness_of_fit_obs 0.978 _refine_ls_restrained_S_all 0.976 _refine_ls_restrained_S_obs 0.975 _refine_ls_shift/esd_max 0.078 _refine_ls_shift/esd_mean 0.004 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ni1 Ni 0.48728(6) 0.10363(3) 0.73318(3) 0.0403(2) Uani 1 d . . N1 N 0.4558(4) 0.1554(2) 0.6313(2) 0.0450(10) Uani 1 d . . N2 N 0.3425(4) 0.1309(2) 0.5882(2) 0.0422(10) Uani 1 d . . N3 N 0.2683(4) 0.0910(2) 0.7392(2) 0.0412(10) Uani 1 d . . N4 N 0.1963(4) 0.0645(2) 0.6774(2) 0.0402(10) Uani 1 d . . N5 N 0.4865(4) 0.0020(2) 0.6773(2) 0.0415(10) Uani 1 d . . N6 N 0.3912(4) -0.0021(2) 0.6187(2) 0.0404(10) Uani 1 d . . O1 O 0.7187(5) 0.2379(2) 0.6614(3) 0.0813(14) Uani 1 d . . O2 O 0.5935(5) 0.3348(2) 0.6194(3) 0.0875(15) Uani 1 d . . O3 O 0.2938(5) 0.1626(2) 0.8843(2) 0.0646(11) Uani 1 d . . O4 O 0.1523(5) 0.0716(3) 0.9171(2) 0.0722(12) Uani 1 d . . O5 O 0.6960(5) -0.0471(2) 0.7916(2) 0.0724(12) Uani 1 d . . O6 O 0.7496(4) -0.1350(2) 0.7134(3) 0.0731(13) Uani 1 d . . O7 O 0.5158(5) 0.0555(3) 0.8369(2) 0.0549(10) Uani 1 d D . H7A H 0.5481(66) 0.0812(30) 0.8662(28) 0.071(24) Uiso 1 d D . H7B H 0.5599(69) 0.0211(26) 0.8325(42) 0.090(29) Uiso 1 d D . O8 O 0.4807(5) 0.2069(2) 0.7831(3) 0.0568(10) Uani 1 d D . H8AO H 0.4373(53) 0.1964(30) 0.8154(22) 0.044(19) Uiso 1 d D . H8BO H 0.5441(48) 0.2189(35) 0.8080(31) 0.072(24) Uiso 1 d D . O9 O 0.7055(4) 0.1106(3) 0.7302(3) 0.0575(10) Uani 1 d D . H9A H 0.7234(66) 0.1447(23) 0.7086(30) 0.058(22) Uiso 1 d D . H9B H 0.7485(72) 0.1205(42) 0.7655(25) 0.088(28) Uiso 1 d D . B1 B 0.2748(6) 0.0569(3) 0.6060(3) 0.0420(14) Uani 1 d . . HB1 H 0.2031(45) 0.0423(23) 0.5632(24) 0.029(11) Uiso 1 d . . C1 C 0.1814(7) 0.1695(4) 0.4805(3) 0.067(2) Uani 1 d . . H1A H 0.1383(7) 0.1228(4) 0.4892(3) 0.100 Uiso 1 calc R . H1B H 0.2140(7) 0.1706(4) 0.4314(3) 0.100 Uiso 1 calc R . H1C H 0.1128(7) 0.2078(4) 0.4858(3) 0.100 Uiso 1 calc R . C2 C 0.3049(6) 0.1809(3) 0.5350(3) 0.0499(13) Uani 1 d . . C3 C 0.3968(6) 0.2387(3) 0.5435(3) 0.0565(15) Uani 1 d . . H3A H 0.3975(6) 0.2810(3) 0.5148(3) 0.068 Uiso 1 calc R . C4 C 0.4886(6) 0.2216(3) 0.6033(3) 0.0507(14) Uani 1 d . . C5 C 0.6120(7) 0.2636(3) 0.6320(4) 0.062(2) Uani 1 d . . C6 C 0.7312(16) 0.3804(6) 0.6317(6) 0.146(6) Uani 1 d . . H6A H 0.8155(16) 0.3525(6) 0.6214(6) 0.175 Uiso 1 calc R . H6B H 0.7281(16) 0.4254(6) 0.6032(6) 0.175 Uiso 1 calc R . C7 C 0.7222(13) 0.3924(6) 0.7012(10) 0.192(8) Uani 1 d . . H7E H 0.8020(13) 0.4212(6) 0.7194(10) 0.289 Uiso 1 calc R . H7C H 0.7220(13) 0.3464(6) 0.7270(10) 0.289 Uiso 1 calc R . H7D H 0.6357(13) 0.4184(6) 0.7090(10) 0.289 Uiso 1 calc R . C8 C -0.0397(6) 0.0127(4) 0.6354(3) 0.075(2) Uani 1 d . . H8B H 0.0030(6) 0.0117(4) 0.5888(3) 0.113 Uiso 1 calc R . H8C H -0.1231(6) 0.0431(4) 0.6318(3) 0.113 Uiso 1 calc R . H8D H -0.0658(6) -0.0363(4) 0.6488(3) 0.113 Uiso 1 calc R . C9 C 0.0640(5) 0.0430(3) 0.6930(3) 0.0472(13) Uani 1 d . . C10 C 0.0505(5) 0.0545(3) 0.7666(3) 0.0519(14) Uani 1 d . . H10A H -0.0284(5) 0.0441(3) 0.7933(3) 0.062 Uiso 1 calc R . C11 C 0.1779(5) 0.0848(3) 0.7933(3) 0.0460(13) Uani 1 d . . C12 C 0.2168(6) 0.1112(3) 0.8686(3) 0.0518(14) Uani 1 d . . C13 C 0.1759(10) 0.0930(5) 0.9942(4) 0.101(3) Uani 1 d . . H13A H 0.2185(10) 0.1415(5) 0.9965(4) 0.121 Uiso 1 calc R . H13B H 0.0848(10) 0.0960(5) 1.0163(4) 0.121 Uiso 1 calc R . C14 C 0.2473(40) 0.0534(8) 1.0276(7) 0.537(34) Uani 1 d . . H14A H 0.2590(40) 0.0701(8) 1.0776(7) 0.806 Uiso 1 calc R . H14B H 0.3385(40) 0.0510(8) 1.0067(7) 0.806 Uiso 1 calc R . H14C H 0.2047(40) 0.0055(8) 1.0265(7) 0.806 Uiso 1 calc R . C15 C 0.3198(7) -0.0868(4) 0.5127(3) 0.069(2) Uani 1 d . . H15A H 0.2506(7) -0.0492(4) 0.5013(3) 0.104 Uiso 1 calc R . H15B H 0.2721(7) -0.1323(4) 0.5212(3) 0.104 Uiso 1 calc R . H15C H 0.3797(7) -0.0924(4) 0.4722(3) 0.104 Uiso 1 calc R . C16 C 0.4090(6) -0.0656(3) 0.5809(3) 0.0493(13) Uani 1 d . . C17 C 0.5188(6) -0.1031(3) 0.6160(3) 0.0527(14) Uani 1 d . . H17A H 0.5558(6) -0.1482(3) 0.6026(3) 0.063 Uiso 1 calc R . C18 C 0.5636(5) -0.0600(3) 0.6756(3) 0.0436(12) Uani 1 d . . C19 C 0.6750(6) -0.0786(3) 0.7335(3) 0.0528(14) Uani 1 d . . C20 C 0.8595(10) -0.1613(5) 0.7677(6) 0.133(4) Uani 1 d . . H20A H 0.9374(10) -0.1265(5) 0.7691(6) 0.159 Uiso 1 calc R . H20B H 0.8199(10) -0.1604(5) 0.8158(6) 0.159 Uiso 1 calc R . C21 C 0.9087(20) -0.2221(8) 0.7587(12) 0.312(15) Uani 1 d . . H21A H 0.9789(20) -0.2326(8) 0.7977(12) 0.468 Uiso 1 calc R . H21B H 0.9520(20) -0.2238(8) 0.7122(12) 0.468 Uiso 1 calc R . H21C H 0.8340(20) -0.2579(8) 0.7590(12) 0.468 Uiso 1 calc R . Cl1 Cl 0.7789(2) 0.19522(13) 0.91472(11) 0.0921(6) Uani 1 d . 1 O10 O 0.6525(9) 0.1586(6) 0.9409(4) 0.149(4) Uani 0.850(14) d P 1 O11 O 0.8406(11) 0.1416(6) 0.8735(5) 0.150(5) Uani 0.850(14) d P 1 O12 O 0.8643(9) 0.2190(5) 0.9747(4) 0.132(4) Uani 0.850(14) d P 1 O13 O 0.7236(9) 0.2522(4) 0.8696(5) 0.162(3) Uani 1 d . 1 O10' O 0.7583(37) 0.1338(19) 0.8975(19) 0.060(11) Uiso 0.150(14) d P 2 O11' O 0.9350(72) 0.2195(38) 0.8879(36) 0.181(28) Uiso 0.150(14) d P 2 O12' O 0.7507(122) 0.2278(63) 0.9959(59) 0.277(50) Uiso 0.150(14) d P 2 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 Ni1 0.0381(4) 0.0413(4) 0.0405(4) -0.0041(3) -0.0052(3) 0.0006(3) N1 0.043(2) 0.045(3) 0.046(2) 0.002(2) -0.004(2) 0.000(2) N2 0.040(2) 0.043(2) 0.042(2) 0.002(2) -0.006(2) 0.001(2) N3 0.043(2) 0.042(2) 0.038(2) -0.006(2) -0.001(2) 0.003(2) N4 0.033(2) 0.048(2) 0.039(2) -0.006(2) -0.006(2) -0.001(2) N5 0.044(2) 0.040(2) 0.040(2) -0.002(2) -0.005(2) 0.002(2) N6 0.041(2) 0.042(2) 0.037(2) -0.009(2) -0.001(2) -0.001(2) O1 0.057(3) 0.069(3) 0.116(4) 0.022(3) -0.019(3) -0.014(2) O2 0.083(3) 0.052(3) 0.124(4) 0.013(3) -0.027(3) -0.023(2) O3 0.070(3) 0.069(3) 0.055(2) -0.021(2) 0.007(2) -0.007(2) O4 0.088(3) 0.088(3) 0.040(2) -0.007(2) 0.005(2) -0.019(3) O5 0.083(3) 0.070(3) 0.060(3) -0.009(2) -0.024(2) 0.024(2) O6 0.062(3) 0.064(3) 0.091(3) -0.012(2) -0.019(2) 0.028(2) O7 0.061(3) 0.057(3) 0.046(2) -0.004(2) -0.005(2) 0.005(2) O8 0.056(3) 0.055(3) 0.058(3) -0.010(2) -0.004(3) -0.003(2) O9 0.044(2) 0.060(3) 0.067(3) 0.003(3) -0.007(2) 0.001(2) B1 0.041(3) 0.045(4) 0.039(3) -0.003(3) -0.006(3) 0.001(3) C1 0.066(4) 0.072(4) 0.059(4) 0.014(3) -0.016(3) 0.000(3) C2 0.053(3) 0.053(3) 0.043(3) 0.009(3) -0.003(2) 0.007(3) C3 0.059(4) 0.050(3) 0.060(4) 0.012(3) -0.003(3) 0.001(3) C4 0.051(3) 0.045(3) 0.055(3) 0.004(3) 0.001(3) 0.002(3) C5 0.061(4) 0.054(4) 0.071(4) 0.011(3) -0.001(3) -0.015(3) C6 0.232(15) 0.067(6) 0.129(9) -0.010(6) -0.081(10) -0.010(7) C7 0.108(8) 0.082(7) 0.395(26) -0.036(12) 0.076(13) -0.028(6) C8 0.043(3) 0.115(6) 0.067(4) -0.013(4) -0.004(3) -0.021(4) C9 0.039(3) 0.055(3) 0.047(3) -0.003(3) -0.002(2) -0.001(3) C10 0.037(3) 0.069(4) 0.050(3) -0.006(3) 0.007(2) -0.002(3) C11 0.044(3) 0.049(3) 0.044(3) -0.005(2) 0.000(3) 0.006(2) C12 0.053(3) 0.060(4) 0.042(3) -0.007(3) 0.001(3) 0.011(3) C13 0.143(8) 0.119(7) 0.041(4) 0.001(4) 0.017(4) -0.038(6) C14 1.367(98) 0.133(12) 0.082(9) -0.031(8) -0.208(25) 0.238(29) C15 0.079(4) 0.069(4) 0.058(4) -0.026(3) -0.012(3) 0.008(3) C16 0.054(3) 0.048(3) 0.045(3) -0.010(3) -0.002(3) -0.002(3) C17 0.054(3) 0.046(3) 0.058(3) -0.011(3) 0.002(3) 0.011(3) C18 0.043(3) 0.043(3) 0.046(3) 0.000(2) 0.005(2) 0.001(3) C19 0.049(3) 0.049(3) 0.060(4) 0.001(3) -0.004(3) 0.006(3) C20 0.111(7) 0.104(7) 0.172(9) -0.046(6) -0.076(7) 0.066(6) C21 0.295(21) 0.122(11) 0.480(32) -0.032(15) -0.298(23) 0.056(13) Cl1 0.0875(14) 0.103(2) 0.0823(13) -0.0262(12) -0.0201(11) 0.0099(12) O10 0.108(6) 0.237(11) 0.103(6) -0.027(6) 0.006(5) -0.058(6) O11 0.127(8) 0.207(10) 0.114(6) -0.075(6) -0.018(6) 0.076(7) O12 0.118(6) 0.167(8) 0.106(6) -0.056(5) -0.049(5) -0.024(5) O13 0.163(7) 0.108(5) 0.202(8) 0.006(5) -0.092(6) -0.001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O9 2.064(4) . ? Ni1 O7 2.082(4) . ? Ni1 N1 2.083(4) . ? Ni1 N3 2.085(4) . ? Ni1 O8 2.091(4) . ? Ni1 N5 2.111(4) . ? N1 C4 1.352(7) . ? N1 N2 1.361(6) . ? N2 C2 1.360(6) . ? N2 B1 1.534(7) . ? N3 C11 1.342(6) . ? N3 N4 1.365(5) . ? N4 C9 1.352(6) . ? N4 B1 1.536(7) . ? N5 C18 1.346(6) . ? N5 N6 1.354(5) . ? N6 C16 1.360(6) . ? N6 B1 1.543(7) . ? O1 C5 1.205(7) . ? O2 C5 1.326(7) . ? O2 C6 1.547(13) . ? O3 C12 1.208(7) . ? O4 C12 1.315(7) . ? O4 C13 1.460(8) . ? O5 C19 1.207(7) . ? O6 C19 1.310(7) . ? O6 C20 1.467(8) . ? C1 C2 1.497(8) . ? C2 C3 1.366(8) . ? C3 C4 1.385(7) . ? C4 C5 1.461(8) . ? C6 C7 1.29(2) . ? C8 C9 1.493(7) . ? C9 C10 1.367(7) . ? C10 C11 1.383(7) . ? C11 C12 1.475(8) . ? C13 C14 1.14(2) . ? C15 C16 1.505(7) . ? C16 C17 1.366(8) . ? C17 C18 1.384(7) . ? C18 C19 1.480(8) . ? C20 C21 1.215(15) . ? Cl1 O11 1.380(8) . ? Cl1 O12 1.385(6) . ? Cl1 O13 1.404(7) . ? Cl1 O10 1.469(8) . ? 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 O9 Ni1 O7 88.5(2) . . ? O9 Ni1 N1 92.2(2) . . ? O7 Ni1 N1 177.8(2) . . ? O9 Ni1 N3 176.9(2) . . ? O7 Ni1 N3 89.0(2) . . ? N1 Ni1 N3 90.4(2) . . ? O9 Ni1 O8 90.6(2) . . ? O7 Ni1 O8 89.6(2) . . ? N1 Ni1 O8 88.4(2) . . ? N3 Ni1 O8 91.3(2) . . ? O9 Ni1 N5 91.0(2) . . ? O7 Ni1 N5 93.6(2) . . ? N1 Ni1 N5 88.5(2) . . ? N3 Ni1 N5 87.3(2) . . ? O8 Ni1 N5 176.5(2) . . ? C4 N1 N2 105.4(4) . . ? C4 N1 Ni1 135.6(3) . . ? N2 N1 Ni1 115.3(3) . . ? C2 N2 N1 110.5(4) . . ? C2 N2 B1 130.2(4) . . ? N1 N2 B1 119.3(4) . . ? C11 N3 N4 105.5(4) . . ? C11 N3 Ni1 136.0(3) . . ? N4 N3 Ni1 116.2(3) . . ? C9 N4 N3 110.5(4) . . ? C9 N4 B1 130.2(4) . . ? N3 N4 B1 119.1(4) . . ? C18 N5 N6 105.6(4) . . ? C18 N5 Ni1 139.6(3) . . ? N6 N5 Ni1 114.2(3) . . ? N5 N6 C16 110.4(4) . . ? N5 N6 B1 120.7(4) . . ? C16 N6 B1 128.7(4) . . ? C5 O2 C6 113.6(6) . . ? C12 O4 C13 116.5(5) . . ? C19 O6 C20 116.0(5) . . ? N2 B1 N4 108.9(4) . . ? N2 B1 N6 110.0(4) . . ? N4 B1 N6 108.1(4) . . ? N2 C2 C3 107.5(5) . . ? N2 C2 C1 122.4(5) . . ? C3 C2 C1 130.0(5) . . ? C2 C3 C4 106.1(5) . . ? N1 C4 C3 110.5(5) . . ? N1 C4 C5 121.9(5) . . ? C3 C4 C5 127.5(5) . . ? O1 C5 O2 123.7(6) . . ? O1 C5 C4 125.4(6) . . ? O2 C5 C4 110.9(5) . . ? C7 C6 O2 97.4(12) . . ? N4 C9 C10 107.5(4) . . ? N4 C9 C8 122.3(5) . . ? C10 C9 C8 130.3(5) . . ? C9 C10 C11 106.0(5) . . ? N3 C11 C10 110.6(4) . . ? N3 C11 C12 121.2(5) . . ? C10 C11 C12 128.2(5) . . ? O3 C12 O4 124.2(5) . . ? O3 C12 C11 125.7(5) . . ? O4 C12 C11 110.0(5) . . ? C14 C13 O4 113.1(10) . . ? N6 C16 C17 107.6(4) . . ? N6 C16 C15 123.6(5) . . ? C17 C16 C15 128.8(5) . . ? C16 C17 C18 105.6(5) . . ? N5 C18 C17 110.7(5) . . ? N5 C18 C19 122.5(5) . . ? C17 C18 C19 126.7(5) . . ? O5 C19 O6 123.6(5) . . ? O5 C19 C18 125.9(5) . . ? O6 C19 C18 110.5(5) . . ? C21 C20 O6 117.8(9) . . ? O11 Cl1 O12 113.9(6) . . ? O11 Cl1 O13 111.1(6) . . ? O12 Cl1 O13 114.0(5) . . ? O11 Cl1 O10 103.2(7) . . ? O12 Cl1 O10 109.4(5) . . ? O13 Cl1 O10 104.2(6) . . ? _refine_diff_density_max 0.620 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.065 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'B.S. Hammes' 'M.W. Carrano' 'C.J. Carrano' _publ_contact_author_name 'Dr Carl J Carano' _publ_contact_author_address ; Dr Carl J Carano Department of Chemistry & Biochemistry Southwest Texas State University San Marcos TX 78666 UNITED STATES OF AMERICA ; _publ_contact_author_email 'cc05@swt.edu' data_bsh81 _database_code_CSD 161749 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H34 B Cl3 Mn N6 O14' _chemical_formula_weight 778.65 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 '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 11.8559(12) _cell_length_b 12.9935(13) _cell_length_c 12.9957(13) _cell_angle_alpha 72.828(9) _cell_angle_beta 67.473(10) _cell_angle_gamma 87.706(9) _cell_volume 1760.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 5.14 _cell_measurement_theta_max 12.80 _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 1.469 _exptl_crystal_density_method ? _exptl_crystal_F_000 802 _exptl_absorpt_coefficient_mu 0.671 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4784 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4523 _reflns_number_observed 3750 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 7 with very negative F^2^ or 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 w=1/[\s^2^(Fo^2^)+(0.1079P)^2^+2.2061P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0187(25) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4516 _refine_ls_number_parameters 501 _refine_ls_number_restraints 43 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_obs 0.0577 _refine_ls_wR_factor_all 0.1888 _refine_ls_wR_factor_obs 0.1650 _refine_ls_goodness_of_fit_all 1.040 _refine_ls_goodness_of_fit_obs 1.043 _refine_ls_restrained_S_all 1.075 _refine_ls_restrained_S_obs 1.042 _refine_ls_shift/esd_max 0.701 _refine_ls_shift/esd_mean 0.042 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn1 Mn 0.75294(6) 0.79368(5) 0.95149(6) 0.0540(3) Uani 1 d . . N1 N 0.6330(3) 0.7162(3) 0.8912(3) 0.0508(9) Uani 1 d . . N2 N 0.6633(3) 0.6186(3) 0.8739(3) 0.0479(9) Uani 1 d . . N3 N 0.7595(3) 0.6206(3) 1.0559(3) 0.0560(10) Uani 1 d . . N4 N 0.7947(3) 0.5502(3) 0.9919(3) 0.0512(9) Uani 1 d . . N5 N 0.9094(3) 0.7570(3) 0.7975(3) 0.0526(9) Uani 1 d . . N6 N 0.8920(3) 0.6619(3) 0.7794(3) 0.0516(9) Uani 1 d . . O1 O 0.5058(4) 0.9065(3) 0.9089(4) 0.0877(12) Uani 1 d . . O2 O 0.3599(3) 0.8319(3) 0.8828(4) 0.0822(11) Uani 1 d . . O3 O 0.6801(5) 0.6987(5) 1.2553(4) 0.120(2) Uani 1 d . . O4 O 0.7872(7) 0.5765(6) 1.3254(5) 0.166(3) Uani 1 d . . O5 O 1.0218(4) 0.9640(3) 0.7619(3) 0.0839(12) Uani 1 d . . O6 O 1.1144(4) 0.9734(3) 0.5750(3) 0.0802(11) Uani 1 d . . O7 O 0.8866(4) 0.8572(5) 0.9971(4) 0.0851(12) Uani 1 d D . O8 O 0.5995(4) 0.8203(4) 1.0964(4) 0.0818(11) Uani 1 d D . O9 O 0.7471(5) 0.9525(4) 0.8421(5) 0.0926(14) Uani 1 d D . C1 C 0.5822(5) 0.4702(4) 0.8278(5) 0.0660(13) Uani 1 d . . H1A H 0.6556(5) 0.4387(4) 0.8319(5) 0.099 Uiso 1 calc R . H1B H 0.5825(5) 0.4801(4) 0.7515(5) 0.099 Uiso 1 calc R . H1C H 0.5121(5) 0.4231(4) 0.8857(5) 0.099 Uiso 1 calc R . C2 C 0.5768(4) 0.5764(4) 0.8498(4) 0.0516(11) Uani 1 d . . C3 C 0.4888(4) 0.6486(4) 0.8521(4) 0.0571(12) Uani 1 d . . H3A H 0.4184(4) 0.6420(4) 0.8384(4) 0.069 Uiso 1 calc R . C4 C 0.5260(4) 0.7329(4) 0.8788(4) 0.0512(11) Uani 1 d . . C5 C 0.4658(4) 0.8329(4) 0.8915(4) 0.0580(12) Uani 1 d . . C6 C 0.2893(6) 0.9253(6) 0.8955(8) 0.103(2) Uani 1 d . . H6A H 0.2036(6) 0.9014(6) 0.9428(8) 0.124 Uiso 1 calc R . H6B H 0.3186(6) 0.9646(6) 0.9347(8) 0.124 Uiso 1 calc R . C7 C 0.3013(23) 0.9898(15) 0.7905(17) 0.336(16) Uani 1 d . . H7A H 0.2549(23) 1.0513(15) 0.7989(17) 0.504 Uiso 1 calc R . H7B H 0.2715(23) 0.9509(15) 0.7524(17) 0.504 Uiso 1 calc R . H7C H 0.3862(23) 1.0139(15) 0.7443(17) 0.504 Uiso 1 calc R . C8 C 0.8795(5) 0.3690(4) 1.0031(5) 0.0757(15) Uani 1 d . . H8A H 0.8762(5) 0.3835(4) 0.9275(5) 0.114 Uiso 1 calc R . H8B H 0.8290(5) 0.3040(4) 1.0552(5) 0.114 Uiso 1 calc R . H8C H 0.9625(5) 0.3602(4) 0.9964(5) 0.114 Uiso 1 calc R . C9 C 0.8339(4) 0.4609(4) 1.0499(4) 0.0577(12) Uani 1 d . . C10 C 0.8235(5) 0.4732(4) 1.1541(5) 0.0678(14) Uani 1 d . . H10A H 0.8436(5) 0.4250(4) 1.2121(5) 0.081 Uiso 1 calc R . C11 C 0.7764(4) 0.5728(4) 1.1547(4) 0.0645(13) Uani 1 d . . C12 C 0.7421(6) 0.6236(6) 1.2474(5) 0.092(2) Uani 1 d . . C13 C 0.7724(17) 0.6369(15) 1.4197(12) 0.218(8) Uani 1 d . . H13A H 0.8453(17) 0.6375(15) 1.4365(12) 0.261 Uiso 1 calc R . H13B H 0.7484(17) 0.7098(15) 1.3979(12) 0.261 Uiso 1 calc R . C14 C 0.6871(25) 0.5732(14) 1.5010(17) 0.305(14) Uani 1 d . . H14A H 0.6629(25) 0.5959(14) 1.5698(17) 0.457 Uiso 1 calc R . H14B H 0.7141(25) 0.5017(14) 1.5169(17) 0.457 Uiso 1 calc R . H14C H 0.6186(25) 0.5729(14) 1.4788(17) 0.457 Uiso 1 calc R . C15 C 0.9715(6) 0.5655(5) 0.6276(5) 0.084(2) Uani 1 d . . H15A H 0.9109(6) 0.5096(5) 0.6866(5) 0.127 Uiso 1 calc R . H15B H 1.0511(6) 0.5384(5) 0.6097(5) 0.127 Uiso 1 calc R . H15C H 0.9539(6) 0.5877(5) 0.5584(5) 0.127 Uiso 1 calc R . C16 C 0.9693(4) 0.6609(4) 0.6719(4) 0.0582(12) Uani 1 d . . C17 C 1.0392(4) 0.7574(4) 0.6176(4) 0.0631(13) Uani 1 d . . H17A H 1.0999(4) 0.7800(4) 0.5426(4) 0.076 Uiso 1 calc R . C18 C 0.9999(4) 0.8148(4) 0.6985(4) 0.0560(12) Uani 1 d . . C19 C 1.0439(4) 0.9241(4) 0.6844(4) 0.0635(13) Uani 1 d . . C20 C 1.1646(6) 1.0832(5) 0.5462(5) 0.090(2) Uani 1 d . . H20A H 1.2089(6) 1.0858(5) 0.5946(5) 0.108 Uiso 1 calc R . H20B H 1.0992(6) 1.1310(5) 0.5597(5) 0.108 Uiso 1 calc R . C21 C 1.2489(7) 1.1174(7) 0.4205(6) 0.115(3) Uani 1 d . . H21A H 1.2836(7) 1.1899(7) 0.3989(6) 0.173 Uiso 1 calc R . H21B H 1.2041(7) 1.1146(7) 0.3734(6) 0.173 Uiso 1 calc R . H21C H 1.3134(7) 1.0696(7) 0.4082(6) 0.173 Uiso 1 calc R . B1 B 0.7880(5) 0.5759(4) 0.8713(5) 0.0514(12) Uani 1 d . . HB1 H 0.8008(39) 0.5113(37) 0.8466(36) 0.052(12) Uiso 1 d . . Cl1 Cl 0.77909(12) 1.24182(10) 0.73260(11) 0.0724(4) Uani 1 d D 1 O10 O 0.8258(8) 1.2831(7) 0.7977(9) 0.175(6) Uani 0.80(2) d PD 1 O11 O 0.6604(4) 1.1935(4) 0.8035(9) 0.192(7) Uani 0.80(2) d PD 1 O12 O 0.7761(8) 1.3258(5) 0.6374(3) 0.122(4) Uani 0.80(2) d PD 1 O13 O 0.8542(4) 1.1644(3) 0.6922(3) 0.106(2) Uani 1 d D 1 O10' O 0.7044(26) 1.2080(22) 0.8341(13) 0.083(13) Uani 0.20(2) d PU 2 O12' O 0.8549(35) 1.3198(29) 0.7117(50) 0.193(30) Uani 0.20(2) d PU 2 O11' O 0.6987(62) 1.2884(98) 0.6838(64) 0.297(57) Uani 0.20(2) d P 2 O15 O 0.9712(5) 0.8402(5) 1.1672(5) 0.124(2) Uani 1 d . . C35 C 0.4014(16) 0.7829(11) 0.4799(12) 0.258(10) Uani 1 d D 1 Cl3' Cl 0.3814(13) 0.6614(13) 0.5665(13) 0.353(11) Uani 0.503(15) d PD 1 Cl2' Cl 0.4545(18) 0.8703(17) 0.5214(21) 0.370(14) Uani 0.503(15) d PD 1 Cl3 Cl 0.3739(13) 0.7808(13) 0.6131(7) 0.315(10) Uani 0.497(15) d PD 2 Cl2 Cl 0.4901(21) 0.8876(16) 0.3905(13) 0.465(16) Uani 0.497(15) d PD 2 H7E H 0.9060(58) 0.8448(52) 1.0460(41) 0.086(23) Uiso 1 d D . H9A H 0.7909(49) 0.9996(38) 0.8066(51) 0.089(23) Uiso 1 d D . H9B H 0.6834(32) 0.9653(64) 0.8594(70) 0.117(32) Uiso 1 d D . H8E H 0.5441(46) 0.8315(66) 1.0847(70) 0.115(32) Uiso 1 d D . H8D H 0.6096(100) 0.7830(71) 1.1457(64) 0.168(49) Uiso 1 d D . H7D H 0.9145(70) 0.8967(52) 0.9394(38) 0.117(32) Uiso 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 Mn1 0.0535(5) 0.0556(5) 0.0580(5) -0.0263(3) -0.0205(3) 0.0060(3) N1 0.045(2) 0.051(2) 0.056(2) -0.018(2) -0.018(2) 0.002(2) N2 0.047(2) 0.048(2) 0.050(2) -0.019(2) -0.017(2) 0.004(2) N3 0.059(2) 0.060(2) 0.052(2) -0.020(2) -0.023(2) 0.013(2) N4 0.047(2) 0.050(2) 0.059(2) -0.018(2) -0.022(2) 0.006(2) N5 0.049(2) 0.059(2) 0.050(2) -0.023(2) -0.015(2) 0.000(2) N6 0.046(2) 0.060(2) 0.052(2) -0.026(2) -0.017(2) 0.008(2) O1 0.070(2) 0.074(2) 0.143(4) -0.053(3) -0.052(2) 0.018(2) O2 0.065(2) 0.076(2) 0.127(3) -0.043(2) -0.052(2) 0.024(2) O3 0.153(5) 0.154(5) 0.094(3) -0.071(3) -0.072(3) 0.079(4) O4 0.239(7) 0.237(7) 0.113(4) -0.110(4) -0.133(5) 0.148(6) O5 0.092(3) 0.079(3) 0.066(2) -0.027(2) -0.009(2) -0.025(2) O6 0.087(3) 0.076(2) 0.060(2) -0.012(2) -0.015(2) -0.019(2) O7 0.080(3) 0.115(4) 0.065(3) -0.028(3) -0.031(3) -0.018(3) O8 0.070(3) 0.107(3) 0.075(3) -0.046(3) -0.023(2) 0.028(3) O9 0.072(3) 0.058(3) 0.135(4) -0.008(3) -0.042(3) -0.004(2) C1 0.064(3) 0.068(3) 0.073(3) -0.034(3) -0.025(3) -0.001(2) C2 0.049(3) 0.059(3) 0.047(2) -0.019(2) -0.015(2) -0.004(2) C3 0.047(3) 0.068(3) 0.061(3) -0.021(2) -0.024(2) -0.004(2) C4 0.043(2) 0.058(3) 0.045(2) -0.011(2) -0.013(2) 0.001(2) C5 0.047(3) 0.063(3) 0.063(3) -0.017(2) -0.022(2) 0.005(2) C6 0.087(4) 0.095(5) 0.157(7) -0.058(5) -0.068(5) 0.044(4) C7 0.604(40) 0.331(21) 0.320(21) -0.242(19) -0.366(27) 0.358(27) C8 0.070(3) 0.059(3) 0.100(4) -0.023(3) -0.037(3) 0.013(3) C9 0.045(3) 0.054(3) 0.070(3) -0.011(2) -0.023(2) 0.001(2) C10 0.062(3) 0.072(3) 0.070(3) -0.008(3) -0.036(3) 0.006(3) C11 0.057(3) 0.080(4) 0.060(3) -0.020(3) -0.027(2) 0.011(3) C12 0.099(5) 0.126(5) 0.068(4) -0.042(4) -0.044(3) 0.034(4) C13 0.300(21) 0.255(19) 0.150(11) -0.082(12) -0.138(13) 0.140(17) C14 0.484(38) 0.193(16) 0.178(16) -0.001(12) -0.116(21) 0.112(20) C15 0.091(4) 0.088(4) 0.073(4) -0.049(3) -0.012(3) 0.006(3) C16 0.052(3) 0.072(3) 0.056(3) -0.031(2) -0.018(2) 0.011(2) C17 0.050(3) 0.080(3) 0.052(3) -0.025(3) -0.008(2) 0.001(2) C18 0.048(3) 0.064(3) 0.052(3) -0.016(2) -0.016(2) -0.003(2) C19 0.051(3) 0.080(3) 0.054(3) -0.021(3) -0.012(2) -0.007(2) C20 0.095(4) 0.078(4) 0.077(4) -0.005(3) -0.022(3) -0.026(3) C21 0.109(5) 0.120(6) 0.079(4) 0.003(4) -0.018(4) -0.027(4) B1 0.051(3) 0.048(3) 0.058(3) -0.024(2) -0.018(2) 0.007(2) Cl1 0.0765(9) 0.0648(8) 0.0674(9) -0.0233(7) -0.0173(8) 0.0120(7) O10 0.242(15) 0.191(10) 0.225(12) -0.153(10) -0.172(12) 0.110(10) O11 0.054(5) 0.161(8) 0.250(16) -0.001(9) 0.014(7) 0.001(4) O12 0.162(9) 0.089(5) 0.078(4) 0.000(3) -0.027(5) 0.037(5) O13 0.105(3) 0.078(3) 0.108(3) -0.036(2) -0.006(3) 0.020(2) O10' 0.083(21) 0.106(19) 0.005(9) 0.007(8) 0.022(10) 0.029(15) O12' 0.141(29) 0.103(23) 0.249(48) -0.096(29) 0.058(32) -0.117(24) O11' 0.188(55) 0.631(182) 0.187(60) -0.199(83) -0.148(51) 0.124(74) O15 0.141(4) 0.152(5) 0.125(4) -0.067(4) -0.084(4) 0.018(4) C35 0.281(19) 0.330(23) 0.153(12) 0.007(13) -0.118(13) -0.132(17) Cl3' 0.307(15) 0.333(18) 0.259(13) 0.013(13) -0.002(10) -0.128(13) Cl2' 0.376(23) 0.446(28) 0.445(36) -0.302(28) -0.205(25) 0.090(20) Cl3 0.359(16) 0.366(20) 0.172(8) 0.068(10) -0.147(10) -0.161(15) Cl2 0.599(35) 0.500(30) 0.180(12) -0.091(15) -0.044(16) 0.098(25) _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 Mn1 O9 2.148(5) . ? Mn1 O7 2.158(4) . ? Mn1 O8 2.164(4) . ? Mn1 N1 2.255(4) . ? Mn1 N3 2.274(4) . ? Mn1 N5 2.307(4) . ? N1 C4 1.340(5) . ? N1 N2 1.363(5) . ? N2 C2 1.358(6) . ? N2 B1 1.550(6) . ? N3 C11 1.339(6) . ? N3 N4 1.362(5) . ? N4 C9 1.356(6) . ? N4 B1 1.536(7) . ? N5 C18 1.344(6) . ? N5 N6 1.361(5) . ? N6 C16 1.349(6) . ? N6 B1 1.546(6) . ? O1 C5 1.198(6) . ? O2 C5 1.304(6) . ? O2 C6 1.461(7) . ? O3 C12 1.203(8) . ? O4 C12 1.308(8) . ? O4 C13 1.593(15) . ? O5 C19 1.203(6) . ? O6 C19 1.313(6) . ? O6 C20 1.453(7) . ? C1 C2 1.483(7) . ? C2 C3 1.373(7) . ? C3 C4 1.376(6) . ? C4 C5 1.479(7) . ? C6 C7 1.33(2) . ? C8 C9 1.488(7) . ? C9 C10 1.367(7) . ? C10 C11 1.391(7) . ? C11 C12 1.457(8) . ? C13 C14 1.25(2) . ? C15 C16 1.508(7) . ? C16 C17 1.368(7) . ? C17 C18 1.393(7) . ? C18 C19 1.468(7) . ? C20 C21 1.490(9) . ? Cl1 O12 1.398(3) . ? Cl1 O11 1.400(3) . ? Cl1 O10 1.400(3) . ? Cl1 O13 1.401(3) . ? O10' O11' 1.95(7) . ? C35 Cl3' 1.610(12) . ? C35 Cl2' 1.629(12) . ? 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 O9 Mn1 O7 89.8(2) . . ? O9 Mn1 O8 90.6(2) . . ? O7 Mn1 O8 93.3(2) . . ? O9 Mn1 N1 92.8(2) . . ? O7 Mn1 N1 172.6(2) . . ? O8 Mn1 N1 93.5(2) . . ? O9 Mn1 N3 175.6(2) . . ? O7 Mn1 N3 93.4(2) . . ? O8 Mn1 N3 92.3(2) . . ? N1 Mn1 N3 83.62(14) . . ? O9 Mn1 N5 91.0(2) . . ? O7 Mn1 N5 89.7(2) . . ? O8 Mn1 N5 176.6(2) . . ? N1 Mn1 N5 83.35(13) . . ? N3 Mn1 N5 85.89(13) . . ? C4 N1 N2 105.7(3) . . ? C4 N1 Mn1 137.2(3) . . ? N2 N1 Mn1 116.6(2) . . ? C2 N2 N1 110.2(3) . . ? C2 N2 B1 128.8(4) . . ? N1 N2 B1 120.6(3) . . ? C11 N3 N4 105.5(4) . . ? C11 N3 Mn1 135.6(3) . . ? N4 N3 Mn1 114.8(3) . . ? C9 N4 N3 110.5(4) . . ? C9 N4 B1 128.2(4) . . ? N3 N4 B1 121.4(4) . . ? C18 N5 N6 105.3(3) . . ? C18 N5 Mn1 136.3(3) . . ? N6 N5 Mn1 115.4(2) . . ? C16 N6 N5 110.7(4) . . ? C16 N6 B1 128.1(4) . . ? N5 N6 B1 120.9(3) . . ? C5 O2 C6 117.2(5) . . ? C12 O4 C13 115.2(7) . . ? C19 O6 C20 117.8(4) . . ? N2 C2 C3 107.2(4) . . ? N2 C2 C1 123.6(4) . . ? C3 C2 C1 129.2(4) . . ? C2 C3 C4 106.0(4) . . ? N1 C4 C3 110.8(4) . . ? N1 C4 C5 120.3(4) . . ? C3 C4 C5 128.8(4) . . ? O1 C5 O2 122.7(5) . . ? O1 C5 C4 125.9(4) . . ? O2 C5 C4 111.3(4) . . ? C7 C6 O2 109.5(8) . . ? N4 C9 C10 107.7(4) . . ? N4 C9 C8 123.7(5) . . ? C10 C9 C8 128.6(5) . . ? C9 C10 C11 105.4(4) . . ? N3 C11 C10 110.9(4) . . ? N3 C11 C12 120.6(5) . . ? C10 C11 C12 128.4(5) . . ? O3 C12 O4 122.2(6) . . ? O3 C12 C11 126.5(6) . . ? O4 C12 C11 111.3(6) . . ? C14 C13 O4 95.7(19) . . ? N6 C16 C17 107.9(4) . . ? N6 C16 C15 122.6(4) . . ? C17 C16 C15 129.5(4) . . ? C16 C17 C18 105.3(4) . . ? N5 C18 C17 110.7(4) . . ? N5 C18 C19 121.4(4) . . ? C17 C18 C19 127.9(4) . . ? O5 C19 O6 123.5(5) . . ? O5 C19 C18 125.4(4) . . ? O6 C19 C18 111.1(4) . . ? O6 C20 C21 107.6(5) . . ? N4 B1 N6 110.3(4) . . ? N4 B1 N2 111.2(4) . . ? N6 B1 N2 108.8(4) . . ? O12 Cl1 O11 109.56(9) . . ? O12 Cl1 O10 109.53(9) . . ? O11 Cl1 O10 109.43(9) . . ? O12 Cl1 O13 109.55(9) . . ? O11 Cl1 O13 109.39(9) . . ? O10 Cl1 O13 109.37(9) . . ? Cl3' C35 Cl2' 113.3(13) . . ? _refine_diff_density_max 0.575 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.063 data_bsh78 _database_code_CSD 161750 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H30 B Cl Cu N6 O15' _chemical_formula_weight 716.31 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.106(3) _cell_length_b 12.6519(11) _cell_length_c 13.012(2) _cell_angle_alpha 106.982(11) _cell_angle_beta 108.75(3) _cell_angle_gamma 103.97(2) _cell_volume 1676.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 37 _cell_measurement_theta_min 5.06 _cell_measurement_theta_max 12.49 _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 1.419 _exptl_crystal_density_method ? _exptl_crystal_F_000 738 _exptl_absorpt_coefficient_mu 0.803 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4402 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 22.49 _reflns_number_total 4157 _reflns_number_observed 3480 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or 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 w=1/[\s^2^(Fo^2^)+(0.1141P)^2^+2.5769P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4152 _refine_ls_number_parameters 443 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_obs 0.0602 _refine_ls_wR_factor_all 0.1979 _refine_ls_wR_factor_obs 0.1766 _refine_ls_goodness_of_fit_all 1.131 _refine_ls_goodness_of_fit_obs 1.146 _refine_ls_restrained_S_all 1.163 _refine_ls_restrained_S_obs 1.145 _refine_ls_shift/esd_max 0.007 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.62995(6) 0.51126(6) 0.72423(5) 0.0426(3) Uani 1 d . . O1 O 0.7041(4) 0.6605(4) 0.5891(4) 0.0630(12) Uani 1 d . . O2 O 0.8887(5) 0.8085(5) 0.6546(5) 0.088(2) Uani 1 d . . O3 O 0.3965(4) 0.5809(4) 0.6382(4) 0.0654(12) Uani 1 d . . O4 O 0.2745(5) 0.6027(6) 0.7335(4) 0.085(2) Uani 1 d . . O5 O 0.5271(4) 0.1919(4) 0.6474(4) 0.0670(12) Uani 1 d . . O6 O 0.6298(4) 0.1025(4) 0.7471(4) 0.0649(12) Uani 1 d . . O7 O 0.6858(6) 0.4384(5) 0.6026(4) 0.0682(13) Uani 1 d D . H7 H 0.6886(94) 0.3825(55) 0.5875(87) 0.107(39) Uiso 1 d D . O8 O 0.4642(4) 0.3790(4) 0.6346(4) 0.0550(11) Uani 1 d D . H8 H 0.4708(53) 0.3247(47) 0.6243(50) 0.032(18) Uiso 1 d D . N1 N 0.7882(4) 0.6528(4) 0.8140(4) 0.0445(11) Uani 1 d . . N2 N 0.8461(4) 0.6907(4) 0.9344(4) 0.0445(11) Uani 1 d . . N3 N 0.5757(4) 0.5925(4) 0.8440(4) 0.0437(11) Uani 1 d . . N4 N 0.6490(4) 0.6211(4) 0.9595(4) 0.0430(11) Uani 1 d . . N5 N 0.6913(4) 0.4118(4) 0.8434(4) 0.0459(11) Uani 1 d . . N6 N 0.7782(4) 0.4930(4) 0.9530(4) 0.0434(11) Uani 1 d . . C1 C 1.0261(6) 0.8596(6) 1.1110(6) 0.067(2) Uani 1 d . . H1A H 0.9976(6) 0.8163(6) 1.1530(6) 0.100 Uiso 1 calc R . H1B H 1.0211(6) 0.9368(6) 1.1373(6) 0.100 Uiso 1 calc R . H1C H 1.1115(6) 0.8683(6) 1.1263(6) 0.100 Uiso 1 calc R . C2 C 0.9450(5) 0.7933(5) 0.9809(5) 0.0471(14) Uani 1 d . . C3 C 0.9532(6) 0.8239(5) 0.8899(6) 0.056(2) Uani 1 d . . H3A H 1.0130(6) 0.8899(5) 0.8955(6) 0.067 Uiso 1 calc R . C4 C 0.8530(5) 0.7351(5) 0.7877(5) 0.0478(14) Uani 1 d . . C5 C 0.8061(6) 0.7272(6) 0.6656(6) 0.053(2) Uani 1 d . . C6 C 0.8557(10) 0.8137(12) 0.5365(9) 0.132(5) Uani 1 d . . H6A H 0.9003(10) 0.7750(12) 0.4981(9) 0.159 Uiso 1 calc R . H6B H 0.7665(10) 0.7686(12) 0.4886(9) 0.159 Uiso 1 calc R . C7 C 0.8781(35) 0.9084(17) 0.5379(16) 0.392(26) Uani 1 d . . H7B H 0.8539(35) 0.9035(17) 0.4583(16) 0.588 Uiso 1 calc R . H7C H 0.9665(35) 0.9534(17) 0.5831(16) 0.588 Uiso 1 calc R . H7D H 0.8324(35) 0.9470(17) 0.5736(16) 0.588 Uiso 1 calc R . C8 C 0.6439(7) 0.6892(7) 1.1578(5) 0.070(2) Uani 1 d . . H8B H 0.7259(7) 0.6852(7) 1.1834(5) 0.105 Uiso 1 calc R . H8C H 0.5910(7) 0.6362(7) 1.1774(5) 0.105 Uiso 1 calc R . H8D H 0.6503(7) 0.7690(7) 1.1968(5) 0.105 Uiso 1 calc R . C9 C 0.5879(6) 0.6534(5) 1.0257(5) 0.0503(15) Uani 1 d . . C10 C 0.4741(6) 0.6462(6) 0.9520(5) 0.056(2) Uani 1 d . . H10A H 0.4117(6) 0.6630(6) 0.9730(5) 0.068 Uiso 1 calc R . C11 C 0.4710(5) 0.6085(5) 0.8395(5) 0.0456(14) Uani 1 d . . C12 C 0.3773(6) 0.5951(5) 0.7251(6) 0.054(2) Uani 1 d . . C13 C 0.1828(10) 0.6080(12) 0.6277(8) 0.126(4) Uani 1 d . . H13A H 0.2245(10) 0.6693(12) 0.6076(8) 0.151 Uiso 1 calc R . H13B H 0.1479(10) 0.5324(12) 0.5602(8) 0.151 Uiso 1 calc R . C14 C 0.0842(9) 0.6342(12) 0.6563(10) 0.122(4) Uani 1 d . . H14A H 0.0242(9) 0.6379(12) 0.5894(10) 0.184 Uiso 1 calc R . H14B H 0.1195(9) 0.7093(12) 0.7229(10) 0.184 Uiso 1 calc R . H14C H 0.0431(9) 0.5728(12) 0.6757(10) 0.184 Uiso 1 calc R . C15 C 0.9435(7) 0.5064(7) 1.1357(6) 0.069(2) Uani 1 d . . H15A H 0.9569(7) 0.5895(7) 1.1604(6) 0.103 Uiso 1 calc R . H15B H 1.0190(7) 0.4952(7) 1.1349(6) 0.103 Uiso 1 calc R . H15C H 0.9217(7) 0.4778(7) 1.1899(6) 0.103 Uiso 1 calc R . C16 C 0.8396(5) 0.4392(5) 1.0144(5) 0.0471(14) Uani 1 d . . C17 C 0.7877(6) 0.3186(6) 0.9433(5) 0.0520(15) Uani 1 d . . H17A H 0.8090(6) 0.2585(6) 0.9617(5) 0.062 Uiso 1 calc R . C18 C 0.6964(5) 0.3069(5) 0.8379(5) 0.0449(13) Uani 1 d . . C19 C 0.6097(6) 0.1973(5) 0.7339(5) 0.0518(15) Uani 1 d . . C20 C 0.5512(8) -0.0136(6) 0.6493(7) 0.080(2) Uani 1 d . . H20A H 0.4632(8) -0.0269(6) 0.6294(7) 0.095 Uiso 1 calc R . H20B H 0.5661(8) -0.0166(6) 0.5798(7) 0.095 Uiso 1 calc R . C21 C 0.5824(11) -0.1044(7) 0.6859(9) 0.119(4) Uani 1 d . . H21A H 0.5316(11) -0.1814(7) 0.6226(9) 0.178 Uiso 1 calc R . H21B H 0.5670(11) -0.1011(7) 0.7544(9) 0.178 Uiso 1 calc R . H21C H 0.6695(11) -0.0909(7) 0.7049(9) 0.178 Uiso 1 calc R . B1 B 0.7850(6) 0.6210(6) 0.9955(6) 0.047(2) Uani 1 d . . H10B H 0.8326(6) 0.6612(6) 1.0818(6) 0.056 Uiso 1 calc R . Cl1 Cl 0.8441(3) 0.2154(2) 0.5723(2) 0.0931(7) Uani 1 d D 1 O9 O 0.7980(8) 0.1372(7) 0.4586(5) 0.165(3) Uani 1 d D 1 O10 O 0.7515(8) 0.2467(11) 0.5924(10) 0.239(15) Uani 0.553(10) d PD 1 O11 O 0.9373(11) 0.3133(8) 0.5919(9) 0.164(7) Uani 0.553(10) d PD 1 O12 O 0.8896(16) 0.1646(9) 0.6458(7) 0.313(29) Uani 0.553(10) d PD 1 O10' O 0.8480(23) 0.3354(17) 0.6026(21) 0.214(13) Uani 0.553(10) d P 2 O11' O 0.9761(15) 0.2347(16) 0.6339(17) 0.150(8) Uani 0.553(10) d P 2 O12' O 0.7873(25) 0.1611(37) 0.6199(29) 0.270(19) Uani 0.553(10) d P 2 O13 O 0.6554(12) 1.1158(9) 1.0882(14) 0.260(8) Uani 1 d . . O14 O 0.7397(6) 0.9360(6) 1.0424(10) 0.165(4) Uani 1 d . . O15 O 0.6614(25) 1.0014(14) 1.1469(20) 0.364(11) 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 0.0516(5) 0.0449(5) 0.0334(4) 0.0159(3) 0.0177(3) 0.0215(3) O1 0.069(3) 0.064(3) 0.050(3) 0.032(2) 0.016(2) 0.016(2) O2 0.071(3) 0.121(4) 0.077(3) 0.068(3) 0.028(3) 0.011(3) O3 0.081(3) 0.080(3) 0.055(3) 0.035(2) 0.032(2) 0.049(3) O4 0.063(3) 0.144(5) 0.072(3) 0.056(3) 0.030(3) 0.059(3) O5 0.076(3) 0.051(3) 0.059(3) 0.019(2) 0.010(2) 0.029(2) O6 0.083(3) 0.046(2) 0.063(3) 0.025(2) 0.021(2) 0.030(2) O7 0.108(4) 0.072(3) 0.056(3) 0.033(3) 0.050(3) 0.056(3) O8 0.064(3) 0.041(3) 0.049(3) 0.016(2) 0.012(2) 0.023(2) N1 0.049(3) 0.048(3) 0.040(3) 0.021(2) 0.020(2) 0.019(2) N2 0.050(3) 0.047(3) 0.037(3) 0.017(2) 0.017(2) 0.020(2) N3 0.052(3) 0.044(3) 0.037(3) 0.014(2) 0.019(2) 0.022(2) N4 0.054(3) 0.043(3) 0.034(2) 0.015(2) 0.019(2) 0.019(2) N5 0.054(3) 0.045(3) 0.038(3) 0.017(2) 0.016(2) 0.021(2) N6 0.049(3) 0.045(3) 0.035(2) 0.019(2) 0.014(2) 0.018(2) C1 0.060(4) 0.060(4) 0.055(4) 0.015(3) 0.008(3) 0.014(3) C2 0.045(3) 0.048(3) 0.046(3) 0.019(3) 0.015(3) 0.019(3) C3 0.049(4) 0.049(3) 0.062(4) 0.028(3) 0.016(3) 0.010(3) C4 0.048(3) 0.054(4) 0.052(4) 0.029(3) 0.024(3) 0.024(3) C5 0.053(4) 0.059(4) 0.058(4) 0.033(3) 0.025(3) 0.023(3) C6 0.101(7) 0.176(11) 0.111(8) 0.103(8) 0.035(6) -0.008(7) C7 0.970(79) 0.187(18) 0.175(16) 0.143(15) 0.294(31) 0.309(33) C8 0.089(5) 0.088(5) 0.043(4) 0.026(3) 0.037(4) 0.038(4) C9 0.064(4) 0.047(3) 0.045(3) 0.020(3) 0.030(3) 0.019(3) C10 0.063(4) 0.064(4) 0.056(4) 0.027(3) 0.035(3) 0.030(3) C11 0.052(4) 0.045(3) 0.046(3) 0.020(3) 0.023(3) 0.021(3) C12 0.061(4) 0.056(4) 0.058(4) 0.027(3) 0.029(3) 0.034(3) C13 0.107(7) 0.218(13) 0.084(6) 0.074(7) 0.030(6) 0.111(8) C14 0.097(7) 0.197(12) 0.133(9) 0.107(9) 0.059(7) 0.088(8) C15 0.071(4) 0.082(5) 0.052(4) 0.035(4) 0.013(3) 0.036(4) C16 0.051(3) 0.063(4) 0.041(3) 0.031(3) 0.021(3) 0.030(3) C17 0.059(4) 0.061(4) 0.054(4) 0.034(3) 0.027(3) 0.036(3) C18 0.053(3) 0.046(3) 0.046(3) 0.025(3) 0.024(3) 0.024(3) C19 0.064(4) 0.047(4) 0.051(4) 0.022(3) 0.027(3) 0.026(3) C20 0.100(6) 0.040(4) 0.077(5) 0.017(3) 0.020(4) 0.023(4) C21 0.150(9) 0.056(5) 0.120(8) 0.027(5) 0.029(7) 0.038(6) B1 0.050(4) 0.053(4) 0.033(3) 0.018(3) 0.013(3) 0.018(3) Cl1 0.129(2) 0.108(2) 0.087(2) 0.0528(14) 0.0658(15) 0.072(2) O9 0.160(8) 0.195(9) 0.087(5) 0.032(5) 0.026(5) 0.047(7) O10 0.277(25) 0.124(13) 0.532(46) 0.196(21) 0.315(31) 0.148(16) O11 0.132(15) 0.185(20) 0.150(15) 0.077(14) 0.043(12) 0.030(15) O12 0.557(75) 0.254(32) 0.122(15) 0.129(20) 0.036(31) 0.218(45) O10' 0.162(17) 0.113(13) 0.231(22) 0.013(13) -0.049(15) 0.083(14) O11' 0.121(12) 0.143(14) 0.152(15) 0.007(11) 0.033(10) 0.091(11) O12' 0.237(27) 0.490(54) 0.322(36) 0.342(41) 0.188(27) 0.208(31) O13 0.218(11) 0.122(7) 0.328(17) 0.096(9) -0.017(11) 0.056(8) O14 0.088(4) 0.067(4) 0.347(13) 0.071(6) 0.115(7) 0.026(3) O15 0.523(33) 0.175(13) 0.387(26) 0.087(15) 0.207(25) 0.129(18) _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 O8 1.981(5) . ? Cu1 N1 1.981(5) . ? Cu1 O7 1.986(5) . ? Cu1 N3 1.991(4) . ? Cu1 N5 2.322(4) . ? O1 C5 1.202(7) . ? O2 C5 1.326(8) . ? O2 C6 1.485(10) . ? O3 C12 1.198(7) . ? O4 C12 1.307(8) . ? O4 C13 1.496(9) . ? O5 C19 1.213(7) . ? O6 C19 1.327(7) . ? O6 C20 1.462(8) . ? N1 C4 1.344(7) . ? N1 N2 1.367(6) . ? N2 C2 1.345(7) . ? N2 B1 1.558(8) . ? N3 C11 1.317(7) . ? N3 N4 1.359(6) . ? N4 C9 1.344(7) . ? N4 B1 1.560(8) . ? N5 C18 1.326(7) . ? N5 N6 1.362(6) . ? N6 C16 1.354(7) . ? N6 B1 1.523(8) . ? C1 C2 1.496(8) . ? C2 C3 1.374(8) . ? C3 C4 1.391(9) . ? C4 C5 1.468(8) . ? C6 C7 1.16(2) . ? C8 C9 1.505(8) . ? C9 C10 1.366(9) . ? C10 C11 1.386(8) . ? C11 C12 1.485(8) . ? C13 C14 1.441(13) . ? C15 C16 1.489(8) . ? C16 C17 1.385(9) . ? C17 C18 1.397(8) . ? C18 C19 1.464(8) . ? C20 C21 1.450(11) . ? Cl1 O12 1.350(5) . ? Cl1 O10 1.351(5) . ? Cl1 O9 1.352(5) . ? Cl1 O11 1.352(5) . ? 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 O8 Cu1 N1 175.2(2) . . ? O8 Cu1 O7 89.9(2) . . ? N1 Cu1 O7 93.0(2) . . ? O8 Cu1 N3 91.7(2) . . ? N1 Cu1 N3 85.1(2) . . ? O7 Cu1 N3 176.7(2) . . ? O8 Cu1 N5 88.7(2) . . ? N1 Cu1 N5 94.7(2) . . ? O7 Cu1 N5 96.8(2) . . ? N3 Cu1 N5 86.1(2) . . ? C5 O2 C6 117.6(6) . . ? C12 O4 C13 114.5(6) . . ? C19 O6 C20 117.7(5) . . ? C4 N1 N2 105.9(4) . . ? C4 N1 Cu1 135.2(4) . . ? N2 N1 Cu1 118.6(3) . . ? C2 N2 N1 110.1(4) . . ? C2 N2 B1 130.8(5) . . ? N1 N2 B1 118.8(4) . . ? C11 N3 N4 107.1(4) . . ? C11 N3 Cu1 134.7(4) . . ? N4 N3 Cu1 116.9(3) . . ? C9 N4 N3 109.3(5) . . ? C9 N4 B1 131.0(5) . . ? N3 N4 B1 119.5(4) . . ? C18 N5 N6 106.3(4) . . ? C18 N5 Cu1 142.0(4) . . ? N6 N5 Cu1 109.0(3) . . ? C16 N6 N5 110.5(4) . . ? C16 N6 B1 129.0(5) . . ? N5 N6 B1 120.1(4) . . ? N2 C2 C3 108.3(5) . . ? N2 C2 C1 123.3(5) . . ? C3 C2 C1 128.4(6) . . ? C2 C3 C4 105.2(5) . . ? N1 C4 C3 110.5(5) . . ? N1 C4 C5 119.3(5) . . ? C3 C4 C5 129.9(6) . . ? O1 C5 O2 125.4(6) . . ? O1 C5 C4 124.1(6) . . ? O2 C5 C4 110.4(6) . . ? C7 C6 O2 115.1(14) . . ? N4 C9 C10 108.0(5) . . ? N4 C9 C8 122.3(6) . . ? C10 C9 C8 129.7(6) . . ? C9 C10 C11 105.5(5) . . ? N3 C11 C10 110.1(5) . . ? N3 C11 C12 119.1(5) . . ? C10 C11 C12 130.6(6) . . ? O3 C12 O4 125.7(6) . . ? O3 C12 C11 123.2(6) . . ? O4 C12 C11 111.1(5) . . ? C14 C13 O4 108.2(8) . . ? N6 C16 C17 107.3(5) . . ? N6 C16 C15 122.6(5) . . ? C17 C16 C15 130.2(5) . . ? C16 C17 C18 105.1(5) . . ? N5 C18 C17 110.8(5) . . ? N5 C18 C19 121.2(5) . . ? C17 C18 C19 128.0(5) . . ? O5 C19 O6 123.5(6) . . ? O5 C19 C18 125.0(5) . . ? O6 C19 C18 111.5(5) . . ? C21 C20 O6 108.4(6) . . ? N6 B1 N2 111.4(5) . . ? N6 B1 N4 109.1(5) . . ? N2 B1 N4 106.3(4) . . ? O12 Cl1 O10 109.56(10) . . ? O12 Cl1 O9 109.54(10) . . ? O10 Cl1 O9 109.44(10) . . ? O12 Cl1 O11 109.51(10) . . ? O10 Cl1 O11 109.44(10) . . ? O9 Cl1 O11 109.34(10) . . ? _refine_diff_density_max 0.812 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.088