# Electronic Supplementary Material (ESI) for Chemical Communications # 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_Co _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H38 B2 Co N18 O12' _chemical_formula_weight 707.15 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.906(3) _cell_length_b 15.906(3) _cell_length_c 10.6715(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2338.1(6) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1107 _exptl_absorpt_coefficient_mu 0.632 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9691 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD Detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8653 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1141 _reflns_number_gt 960 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+4.6929P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1141 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0648 _refine_ls_wR_factor_gt 0.0585 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.15217(12) 0.52405(12) 0.86226(16) 0.0214(4) Uani 1 1 d . . . H1 H 0.1428 0.5139 0.7744 0.026 Uiso 1 1 calc R . . C2 C 0.08567(12) 0.47531(12) 0.95451(16) 0.0218(4) Uani 1 1 d . . . H2 H 0.0208 0.4246 0.9417 0.026 Uiso 1 1 calc R . . B1 B 0.3333 0.6667 0.8697(3) 0.0197(6) Uani 1 3 d S . . N1 N 0.23349(10) 0.58908(10) 0.92120(12) 0.0177(3) Uani 1 1 d . . . N2 N 0.21750(10) 0.58032(10) 1.04562(12) 0.0173(3) Uani 1 1 d . . . N3 N 0.12749(10) 0.51120(10) 1.06727(13) 0.0194(3) Uani 1 1 d . . . Co1 Co 0.3333 0.6667 1.1667 0.01411(15) Uani 1 6 d S . . O1 O 0.08171(9) 0.46229(9) 0.56746(13) 0.0232(3) Uani 1 1 d . . . O2 O 0.02860(10) 0.46143(10) 1.31266(11) 0.0227(3) Uani 1 1 d . . . H1B H 0.3333 0.6667 0.772(3) 0.019(8) Uiso 1 3 d S . . H1O H -0.019(2) 0.408(2) 1.290(2) 0.057(8) Uiso 1 1 d . . . H2O H 0.064(2) 0.4826(19) 1.252(2) 0.057(8) Uiso 1 1 d . . . H3O H 0.0435(18) 0.4763(17) 0.601(2) 0.045(7) Uiso 1 1 d . . . H4O H 0.0728(18) 0.4643(18) 0.489(3) 0.051(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0244(9) 0.0241(9) 0.0194(8) -0.0064(6) -0.0081(7) 0.0148(7) C2 0.0201(8) 0.0198(8) 0.0262(9) -0.0065(7) -0.0064(7) 0.0105(7) B1 0.0242(10) 0.0242(10) 0.0107(14) 0.000 0.000 0.0121(5) N1 0.0213(7) 0.0207(7) 0.0123(6) -0.0022(5) -0.0027(5) 0.0114(6) N2 0.0182(7) 0.0199(7) 0.0128(7) -0.0002(5) -0.0001(5) 0.0089(6) N3 0.0175(7) 0.0186(7) 0.0219(7) -0.0010(5) -0.0011(5) 0.0088(6) Co1 0.01620(19) 0.01620(19) 0.0099(3) 0.000 0.000 0.00810(9) O1 0.0266(7) 0.0281(7) 0.0189(7) -0.0010(5) -0.0020(5) 0.0168(6) O2 0.0248(7) 0.0233(7) 0.0175(6) -0.0009(5) 0.0005(5) 0.0100(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 C1 N1 1.342(2) . ? C1 C2 1.367(2) . ? C1 H1 0.9500 . ? C2 N3 1.355(2) . ? C2 H2 0.9500 . ? B1 N1 1.5449(17) 3_565 ? B1 N1 1.5449(17) . ? B1 N1 1.5449(17) 2_665 ? B1 H1B 1.04(3) . ? N1 N2 1.3459(18) . ? N2 N3 1.3183(19) . ? N2 Co1 2.1022(13) . ? Co1 N2 2.1021(13) 15_557 ? Co1 N2 2.1022(13) 3_565 ? Co1 N2 2.1022(13) 13_567 ? Co1 N2 2.1022(13) 2_665 ? Co1 N2 2.1022(13) 14_457 ? O1 H3O 0.83(3) . ? O1 H4O 0.86(3) . ? O2 H1O 0.85(3) . ? O2 H2O 0.81(3) . ? 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 C1 C2 105.90(14) . . ? N1 C1 H1 127.1 . . ? C2 C1 H1 127.1 . . ? N3 C2 C1 108.84(15) . . ? N3 C2 H2 125.6 . . ? C1 C2 H2 125.6 . . ? N1 B1 N1 108.09(12) 3_565 . ? N1 B1 N1 108.09(12) 3_565 2_665 ? N1 B1 N1 108.09(12) . 2_665 ? N1 B1 H1B 110.82(12) 3_565 . ? N1 B1 H1B 110.82(11) . . ? N1 B1 H1B 110.82(12) 2_665 . ? C1 N1 N2 108.86(13) . . ? C1 N1 B1 131.21(16) . . ? N2 N1 B1 119.93(15) . . ? N3 N2 N1 109.24(12) . . ? N3 N2 Co1 131.97(10) . . ? N1 N2 Co1 118.69(10) . . ? N2 N3 C2 107.17(13) . . ? N2 Co1 N2 180.0 15_557 3_565 ? N2 Co1 N2 93.81(5) 15_557 . ? N2 Co1 N2 86.19(5) 3_565 . ? N2 Co1 N2 86.19(5) 15_557 13_567 ? N2 Co1 N2 93.81(5) 3_565 13_567 ? N2 Co1 N2 180.00(5) . 13_567 ? N2 Co1 N2 93.81(5) 15_557 2_665 ? N2 Co1 N2 86.19(5) 3_565 2_665 ? N2 Co1 N2 86.19(5) . 2_665 ? N2 Co1 N2 93.81(5) 13_567 2_665 ? N2 Co1 N2 86.19(5) 15_557 14_457 ? N2 Co1 N2 93.81(5) 3_565 14_457 ? N2 Co1 N2 93.81(5) . 14_457 ? N2 Co1 N2 86.19(5) 13_567 14_457 ? N2 Co1 N2 180.0 2_665 14_457 ? H3O O1 H4O 105(2) . . ? H1O O2 H2O 106(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N3 -0.11(18) . . . . ? C2 C1 N1 N2 0.19(18) . . . . ? C2 C1 N1 B1 -178.77(13) . . . . ? N1 B1 N1 C1 123.2(2) 3_565 . . . ? N1 B1 N1 C1 -120.0(2) 2_665 . . . ? N1 B1 N1 N2 -55.65(17) 3_565 . . . ? N1 B1 N1 N2 61.11(17) 2_665 . . . ? C1 N1 N2 N3 -0.20(17) . . . . ? B1 N1 N2 N3 178.89(11) . . . . ? C1 N1 N2 Co1 176.52(10) . . . . ? B1 N1 N2 Co1 -4.39(16) . . . . ? N1 N2 N3 C2 0.13(17) . . . . ? Co1 N2 N3 C2 -176.01(11) . . . . ? C1 C2 N3 N2 -0.01(18) . . . . ? N3 N2 Co1 N2 41.40(16) . . . 15_557 ? N1 N2 Co1 N2 -134.44(9) . . . 15_557 ? N3 N2 Co1 N2 -138.60(16) . . . 3_565 ? N1 N2 Co1 N2 45.56(9) . . . 3_565 ? N3 N2 Co1 N2 -66(9) . . . 13_567 ? N1 N2 Co1 N2 118(9) . . . 13_567 ? N3 N2 Co1 N2 134.98(16) . . . 2_665 ? N1 N2 Co1 N2 -40.87(9) . . . 2_665 ? N3 N2 Co1 N2 -45.03(16) . . . 14_457 ? N1 N2 Co1 N2 139.13(9) . . . 14_457 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.240 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 961782' ####################################################################### # # 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_Fe _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H38 B2 Fe N18 O12' _chemical_formula_weight 704.07 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.8445(13) _cell_length_b 15.8445(13) _cell_length_c 10.5951(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2303.5(3) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cube _exptl_crystal_colour red _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9719 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-AXS Smart Apex II' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9106 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1251 _reflns_number_gt 1143 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+4.0601P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1251 _refine_ls_number_parameters 87 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.0000 0.0000 0.0000 0.00917(13) Uani 1 6 d S . . N2 N 0.10972(8) 0.02513(7) 0.10938(10) 0.0117(2) Uani 1 1 d . . . N3 N 0.19890(8) 0.04520(8) 0.08146(10) 0.0138(2) Uani 1 1 d . . . N1 N 0.09877(8) 0.02061(8) 0.23561(10) 0.0129(2) Uani 1 1 d . . . C2 C 0.24525(10) 0.05305(10) 0.19215(13) 0.0167(3) Uani 1 1 d . . . H2 H 0.3107 0.0670 0.2006 0.020 Uiso 1 1 calc R . . C1 C 0.18254(10) 0.03767(9) 0.28979(13) 0.0162(3) Uani 1 1 d . . . H1 H 0.1955 0.0388 0.3775 0.019 Uiso 1 1 calc R . . B1 B 0.0000 0.0000 0.2913(2) 0.0146(5) Uani 1 3 d S . . O1 O 0.30457(8) 0.09784(7) 0.84709(9) 0.0189(2) Uani 1 1 d D . . O2 O 0.20305(7) 0.24957(8) 0.40655(10) 0.0199(2) Uani 1 1 d D . . H1B H 0.0000 0.0000 0.392(3) 0.022(7) Uiso 1 3 d S . . H1' H 0.2677(14) 0.0850(16) 0.9120(17) 0.041(6) Uiso 1 1 d D . . H2' H 0.2041(15) 0.2572(15) 0.3246(15) 0.038(6) Uiso 1 1 d D . . H2" H 0.1887(17) 0.2887(18) 0.439(2) 0.049(7) Uiso 1 1 d D . . H1" H 0.3545(14) 0.0931(18) 0.872(2) 0.058(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01016(15) 0.01016(15) 0.0072(2) 0.000 0.000 0.00508(8) N2 0.0130(5) 0.0120(5) 0.0098(5) 0.0000(4) 0.0004(4) 0.0059(4) N3 0.0118(5) 0.0127(5) 0.0168(5) 0.0009(4) -0.0002(4) 0.0061(4) N1 0.0157(5) 0.0134(5) 0.0092(5) -0.0006(4) -0.0022(4) 0.0070(4) C2 0.0140(6) 0.0145(6) 0.0214(7) 0.0006(5) -0.0047(5) 0.0069(5) C1 0.0180(6) 0.0144(6) 0.0154(6) -0.0005(5) -0.0062(5) 0.0074(5) B1 0.0175(7) 0.0175(7) 0.0090(11) 0.000 0.000 0.0087(4) O1 0.0208(5) 0.0242(5) 0.0146(5) 0.0023(4) 0.0018(4) 0.0135(4) O2 0.0235(5) 0.0221(5) 0.0169(5) 0.0018(4) 0.0009(4) 0.0135(4) _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 Fe1 N2 1.9574(11) 10 ? Fe1 N2 1.9574(11) 2 ? Fe1 N2 1.9574(11) . ? Fe1 N2 1.9574(11) 11 ? Fe1 N2 1.9574(11) 12 ? Fe1 N2 1.9574(11) 3 ? N2 N3 1.3176(15) . ? N2 N1 1.3459(14) . ? N3 C2 1.3560(17) . ? N1 C1 1.3436(17) . ? N1 B1 1.5468(14) . ? C2 C1 1.369(2) . ? C2 H2 0.9500 . ? C1 H1 0.9500 . ? B1 N1 1.5468(14) 3 ? B1 N1 1.5468(14) 2 ? B1 H1B 1.07(3) . ? O1 H1' 0.858(15) . ? O1 H1" 0.873(16) . ? O2 H2' 0.876(15) . ? O2 H2" 0.83(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 N2 Fe1 N2 91.48(4) 10 2 ? N2 Fe1 N2 180.00(8) 10 . ? N2 Fe1 N2 88.52(4) 2 . ? N2 Fe1 N2 88.52(4) 10 11 ? N2 Fe1 N2 180.00(7) 2 11 ? N2 Fe1 N2 91.48(4) . 11 ? N2 Fe1 N2 88.52(4) 10 12 ? N2 Fe1 N2 91.48(4) 2 12 ? N2 Fe1 N2 91.48(4) . 12 ? N2 Fe1 N2 88.52(4) 11 12 ? N2 Fe1 N2 91.48(4) 10 3 ? N2 Fe1 N2 88.52(4) 2 3 ? N2 Fe1 N2 88.52(4) . 3 ? N2 Fe1 N2 91.48(4) 11 3 ? N2 Fe1 N2 180.00(12) 12 3 ? N3 N2 N1 109.27(10) . . ? N3 N2 Fe1 130.73(8) . . ? N1 N2 Fe1 119.99(8) . . ? N2 N3 C2 107.11(11) . . ? C1 N1 N2 109.02(11) . . ? C1 N1 B1 132.29(13) . . ? N2 N1 B1 118.68(12) . . ? N3 C2 C1 109.00(12) . . ? N3 C2 H2 125.5 . . ? C1 C2 H2 125.5 . . ? N1 C1 C2 105.60(11) . . ? N1 C1 H1 127.2 . . ? C2 C1 H1 127.2 . . ? N1 B1 N1 106.38(10) 3 . ? N1 B1 N1 106.38(10) 3 2 ? N1 B1 N1 106.38(10) . 2 ? N1 B1 H1B 112.41(9) 3 . ? N1 B1 H1B 112.41(9) . . ? N1 B1 H1B 112.41(9) 2 . ? H1' O1 H1" 106.0(19) . . ? H2' O2 H2" 107.8(19) . . ? 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 Fe1 N2 N3 20(14) 10 . . . ? N2 Fe1 N2 N3 -136.04(13) 2 . . . ? N2 Fe1 N2 N3 43.96(13) 11 . . . ? N2 Fe1 N2 N3 -44.60(13) 12 . . . ? N2 Fe1 N2 N3 135.40(13) 3 . . . ? N2 Fe1 N2 N1 -158(100) 10 . . . ? N2 Fe1 N2 N1 45.78(7) 2 . . . ? N2 Fe1 N2 N1 -134.22(7) 11 . . . ? N2 Fe1 N2 N1 137.22(7) 12 . . . ? N2 Fe1 N2 N1 -42.78(7) 3 . . . ? N1 N2 N3 C2 0.32(13) . . . . ? Fe1 N2 N3 C2 -178.02(9) . . . . ? N3 N2 N1 C1 -0.30(13) . . . . ? Fe1 N2 N1 C1 178.24(8) . . . . ? N3 N2 N1 B1 178.71(8) . . . . ? Fe1 N2 N1 B1 -2.75(13) . . . . ? N2 N3 C2 C1 -0.22(14) . . . . ? N2 N1 C1 C2 0.15(14) . . . . ? B1 N1 C1 C2 -178.67(10) . . . . ? N3 C2 C1 N1 0.04(15) . . . . ? C1 N1 B1 N1 -123.07(17) . . . 3 ? N2 N1 B1 N1 58.19(13) . . . 3 ? C1 N1 B1 N1 123.81(17) . . . 2 ? N2 N1 B1 N1 -54.93(13) . . . 2 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.423 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 961783' ####################################################################### # # 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_Ni _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H38 B2 N18 Ni O12' _chemical_formula_weight 706.93 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.9039(8) _cell_length_b 15.9039(8) _cell_length_c 10.6402(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2330.7(2) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1110 _exptl_absorpt_coefficient_mu 0.706 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8893 _exptl_absorpt_correction_T_max 0.9014 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8243 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.40 _reflns_number_total 1305 _reflns_number_gt 1277 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1305 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.0000 0.0000 0.0000 0.00934(17) Uani 1 6 d S . . N1 N 0.20421(7) 0.04923(7) 0.09451(9) 0.0157(2) Uani 1 1 d . . . N2 N 0.11466(7) 0.02841(7) 0.11764(8) 0.0128(2) Uani 1 1 d . . . N3 N 0.09951(7) 0.02173(7) 0.24231(9) 0.0136(2) Uani 1 1 d . . . C1 C 0.24720(9) 0.05536(9) 0.20698(11) 0.0181(3) Uani 1 1 d . . . H7 H 0.3121 0.0693 0.2188 0.022 Uiso 1 1 calc R . . C2 C 0.18121(9) 0.03812(8) 0.30100(11) 0.0174(3) Uani 1 1 d . . . H6 H 0.1912 0.0378 0.3890 0.021 Uiso 1 1 calc R . . B1 B 0.0000 0.0000 0.29532(19) 0.0142(4) Uani 1 3 d S . . H1 H 0.0000 0.0000 0.400(2) 0.017 Uiso 1 3 d S . . O1 O 0.30477(7) 0.09902(7) 0.85240(8) 0.0186(2) Uani 1 1 d . . . H2 H 0.4794(14) 0.0464(15) 0.8934(16) 0.022 Uiso 1 1 d . . . H3 H 0.4726(14) 0.0766(13) 1.0155(16) 0.022 Uiso 1 1 d . . . O2 O 0.46285(7) 0.08227(7) 0.93125(8) 0.0194(2) Uani 1 1 d . . . H4 H 0.3519(14) 0.0927(13) 0.8708(15) 0.023 Uiso 1 1 d . . . H5 H 0.2754(14) 0.0932(14) 0.9114(18) 0.023 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01042(19) 0.01042(19) 0.0072(2) 0.000 0.000 0.00521(9) N1 0.0133(5) 0.0148(5) 0.0190(5) 0.0007(3) -0.0005(3) 0.0070(4) N2 0.0128(4) 0.0154(5) 0.0100(5) 0.0002(3) -0.0001(3) 0.0069(3) N3 0.0163(5) 0.0156(4) 0.0087(4) -0.0007(3) -0.0026(3) 0.0078(4) C1 0.0139(5) 0.0160(5) 0.0237(6) -0.0002(4) -0.0056(4) 0.0070(4) C2 0.0185(6) 0.0159(5) 0.0168(5) 0.0001(4) -0.0068(4) 0.0078(4) B1 0.0167(6) 0.0167(6) 0.0092(8) 0.000 0.000 0.0083(3) O1 0.0203(5) 0.0230(5) 0.0152(4) 0.0011(3) 0.0005(3) 0.0128(4) O2 0.0227(5) 0.0211(5) 0.0175(4) 0.0025(3) 0.0014(3) 0.0133(4) _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 N2 2.0670(9) . ? Ni1 N2 2.0670(9) 11 ? Ni1 N2 2.0670(9) 10 ? Ni1 N2 2.0670(9) 12 ? Ni1 N2 2.0670(9) 3 ? Ni1 N2 2.0670(9) 2 ? N1 N2 1.3140(13) . ? N1 C1 1.3573(15) . ? N2 N3 1.3429(12) . ? N3 C2 1.3445(15) . ? N3 B1 1.5476(12) . ? C1 C2 1.3747(17) . ? C1 H7 0.9500 . ? C2 H6 0.9500 . ? B1 N3 1.5476(12) 3 ? B1 N3 1.5476(12) 2 ? B1 H1 1.12(3) . ? O1 H4 0.828(19) . ? O1 H5 0.760(19) . ? O2 H2 0.84(2) . ? O2 H3 0.922(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N2 92.87(4) . 11 ? N2 Ni1 N2 180.00(6) . 10 ? N2 Ni1 N2 87.13(4) 11 10 ? N2 Ni1 N2 92.87(4) . 12 ? N2 Ni1 N2 87.13(4) 11 12 ? N2 Ni1 N2 87.13(4) 10 12 ? N2 Ni1 N2 87.13(4) . 3 ? N2 Ni1 N2 92.87(4) 11 3 ? N2 Ni1 N2 92.87(4) 10 3 ? N2 Ni1 N2 180.00(10) 12 3 ? N2 Ni1 N2 87.13(4) . 2 ? N2 Ni1 N2 180.00(6) 11 2 ? N2 Ni1 N2 92.87(4) 10 2 ? N2 Ni1 N2 92.87(4) 12 2 ? N2 Ni1 N2 87.13(4) 3 2 ? N2 N1 C1 107.25(9) . . ? N1 N2 N3 109.51(8) . . ? N1 N2 Ni1 131.93(7) . . ? N3 N2 Ni1 118.49(7) . . ? N2 N3 C2 109.01(9) . . ? N2 N3 B1 120.04(10) . . ? C2 N3 B1 130.94(11) . . ? N1 C1 C2 108.69(10) . . ? N1 C1 H7 125.7 . . ? C2 C1 H7 125.7 . . ? N3 C2 C1 105.55(9) . . ? N3 C2 H6 127.2 . . ? C1 C2 H6 127.2 . . ? N3 B1 N3 107.50(8) 3 2 ? N3 B1 N3 107.51(8) 3 . ? N3 B1 N3 107.50(8) 2 . ? N3 B1 H1 111.37(8) 3 . ? N3 B1 H1 111.37(8) 2 . ? N3 B1 H1 111.37(8) . . ? H4 O1 H5 109.2(17) . . ? H2 O2 H3 105.9(15) . . ? 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 C1 N1 N2 N3 0.42(12) . . . . ? C1 N1 N2 Ni1 -176.41(8) . . . . ? N2 Ni1 N2 N1 42.41(11) 11 . . . ? N2 Ni1 N2 N1 -159.20(10) 10 . . . ? N2 Ni1 N2 N1 -44.86(11) 12 . . . ? N2 Ni1 N2 N1 135.14(11) 3 . . . ? N2 Ni1 N2 N1 -137.59(11) 2 . . . ? N2 Ni1 N2 N3 -134.19(6) 11 . . . ? N2 Ni1 N2 N3 24.20(8) 10 . . . ? N2 Ni1 N2 N3 138.54(6) 12 . . . ? N2 Ni1 N2 N3 -41.46(6) 3 . . . ? N2 Ni1 N2 N3 45.81(6) 2 . . . ? N1 N2 N3 C2 -0.35(12) . . . . ? Ni1 N2 N3 C2 176.97(7) . . . . ? N1 N2 N3 B1 178.62(8) . . . . ? Ni1 N2 N3 B1 -4.06(11) . . . . ? N2 N1 C1 C2 -0.33(13) . . . . ? N2 N3 C2 C1 0.13(13) . . . . ? B1 N3 C2 C1 -178.69(9) . . . . ? N1 C1 C2 N3 0.12(14) . . . . ? N2 N3 B1 N3 60.26(11) . . . 3 ? C2 N3 B1 N3 -121.02(15) . . . 3 ? N2 N3 B1 N3 -55.22(12) . . . 2 ? C2 N3 B1 N3 123.50(15) . . . 2 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.335 _refine_diff_density_min -0.742 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 961784' ####################################################################### # # 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_Cd _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 B2 Cd N18' _chemical_formula_weight 544.43 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.1072(8) _cell_length_b 13.4631(9) _cell_length_c 15.5981(11) _cell_angle_alpha 90.00 _cell_angle_beta 109.5660(10) _cell_angle_gamma 90.00 _cell_volume 2197.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour clourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 1.036 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9500 _exptl_absorpt_correction_T_max 0.9796 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12707 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 28.51 _reflns_number_total 2674 _reflns_number_gt 2270 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0235P)^2^+2.7910P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2674 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0512 _refine_ls_wR_factor_gt 0.0483 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.2500 0.2500 0.5000 0.01128(6) Uani 1 2 d S . . N3 N 0.04508(13) 0.20191(11) 0.49459(10) 0.0149(3) Uani 1 1 d . . . N1 N 0.34108(14) 0.10585(11) 0.58104(10) 0.0161(3) Uani 1 1 d . . . N2 N 0.22466(14) 0.15712(11) 0.36722(9) 0.0150(3) Uani 1 1 d . . . B1 B -0.27568(18) 0.13816(14) 0.34846(12) 0.0127(4) Uani 1 1 d . . . N4 N -0.15027(13) 0.16024(10) 0.42851(9) 0.0128(3) Uani 1 1 d . . . N5 N 0.24099(13) 0.11921(10) 0.23810(9) 0.0121(3) Uani 1 1 d . . . N8 N 0.26715(13) 0.18964(11) 0.30273(9) 0.0142(3) Uani 1 1 d . . . N6 N 0.33534(13) -0.04448(11) 0.62538(9) 0.0129(3) Uani 1 1 d . . . N9 N -0.04182(13) 0.18535(11) 0.41418(10) 0.0152(3) Uani 1 1 d . . . N7 N 0.26542(14) 0.03799(11) 0.59611(10) 0.0158(3) Uani 1 1 d . . . C6 C -0.13193(16) 0.16127(13) 0.51869(11) 0.0159(3) Uani 1 1 d . . . H6 H -0.1933 0.1467 0.5471 0.019 Uiso 1 1 calc R . . C5 C -0.00732(16) 0.18759(13) 0.56061(11) 0.0157(3) Uani 1 1 d . . . H5 H 0.0349 0.1946 0.6243 0.019 Uiso 1 1 calc R . . C3 C 0.17133(17) 0.06633(13) 0.34397(12) 0.0179(4) Uani 1 1 d . . . H3 H 0.1335 0.0269 0.3786 0.021 Uiso 1 1 calc R . . C4 C 0.18161(17) 0.04162(13) 0.26174(12) 0.0177(4) Uani 1 1 d . . . H4 H 0.1530 -0.0177 0.2282 0.021 Uiso 1 1 calc R . . C2 C 0.45968(18) 0.06698(15) 0.60048(15) 0.0273(4) Uani 1 1 d . . . H2 H 0.5323 0.1004 0.5955 0.033 Uiso 1 1 calc R . . C1 C 0.45650(17) -0.02856(15) 0.62846(14) 0.0243(4) Uani 1 1 d . . . H1 H 0.5254 -0.0744 0.6464 0.029 Uiso 1 1 calc R . . H1B H -0.3444(18) 0.1986(15) 0.3362(13) 0.012(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.01152(9) 0.01333(9) 0.00928(9) -0.00052(6) 0.00387(6) -0.00164(6) N3 0.0134(7) 0.0170(7) 0.0135(7) -0.0004(6) 0.0035(6) -0.0020(6) N1 0.0154(7) 0.0178(7) 0.0148(7) 0.0016(6) 0.0045(6) -0.0023(6) N2 0.0153(7) 0.0184(7) 0.0113(7) -0.0007(5) 0.0044(5) 0.0005(6) B1 0.0120(9) 0.0148(9) 0.0113(9) 0.0008(7) 0.0039(7) -0.0006(7) N4 0.0124(7) 0.0132(7) 0.0133(7) 0.0000(5) 0.0050(5) -0.0007(5) N5 0.0108(6) 0.0137(7) 0.0109(7) -0.0023(5) 0.0024(5) -0.0001(5) N8 0.0151(7) 0.0156(7) 0.0110(7) -0.0026(5) 0.0032(5) 0.0002(6) N6 0.0109(7) 0.0159(7) 0.0109(6) 0.0025(5) 0.0024(5) 0.0011(5) N9 0.0130(7) 0.0183(7) 0.0148(7) -0.0004(6) 0.0055(6) -0.0031(6) N7 0.0161(7) 0.0142(7) 0.0178(7) 0.0023(6) 0.0064(6) 0.0005(6) C6 0.0162(8) 0.0192(9) 0.0135(8) 0.0003(6) 0.0064(7) -0.0019(7) C5 0.0166(8) 0.0181(8) 0.0122(8) -0.0007(6) 0.0044(7) -0.0018(7) C3 0.0219(9) 0.0180(9) 0.0155(8) -0.0001(7) 0.0085(7) -0.0021(7) C4 0.0205(9) 0.0156(8) 0.0186(9) -0.0022(7) 0.0087(7) -0.0037(7) C2 0.0136(9) 0.0263(10) 0.0413(12) 0.0128(9) 0.0082(8) -0.0015(8) C1 0.0108(8) 0.0271(10) 0.0333(11) 0.0114(8) 0.0052(8) 0.0017(7) _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 Cd1 N3 2.3406(14) 7_556 ? Cd1 N3 2.3406(14) . ? Cd1 N1 2.3518(15) . ? Cd1 N1 2.3518(15) 7_556 ? Cd1 N2 2.3542(14) 7_556 ? Cd1 N2 2.3542(14) . ? N3 N9 1.3205(19) . ? N3 C5 1.356(2) . ? N1 N7 1.315(2) . ? N1 C2 1.354(2) . ? N2 N8 1.3208(19) . ? N2 C3 1.354(2) . ? B1 N6 1.542(2) 5_556 ? B1 N5 1.544(2) 2 ? B1 N4 1.557(2) . ? B1 H1B 1.088(19) . ? N4 N9 1.3399(19) . ? N4 C6 1.352(2) . ? N5 N8 1.3429(19) . ? N5 C4 1.351(2) . ? N5 B1 1.544(2) 2 ? N6 N7 1.344(2) . ? N6 C1 1.348(2) . ? N6 B1 1.542(2) 5_556 ? C6 C5 1.365(2) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C3 C4 1.366(2) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C2 C1 1.363(3) . ? C2 H2 0.9500 . ? C1 H1 0.9500 . ? 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 N3 Cd1 N3 180.0 7_556 . ? N3 Cd1 N1 88.33(5) 7_556 . ? N3 Cd1 N1 91.67(5) . . ? N3 Cd1 N1 91.67(5) 7_556 7_556 ? N3 Cd1 N1 88.33(5) . 7_556 ? N1 Cd1 N1 180.00(7) . 7_556 ? N3 Cd1 N2 89.60(5) 7_556 7_556 ? N3 Cd1 N2 90.40(5) . 7_556 ? N1 Cd1 N2 93.57(5) . 7_556 ? N1 Cd1 N2 86.43(5) 7_556 7_556 ? N3 Cd1 N2 90.40(5) 7_556 . ? N3 Cd1 N2 89.60(5) . . ? N1 Cd1 N2 86.43(5) . . ? N1 Cd1 N2 93.57(5) 7_556 . ? N2 Cd1 N2 180.0 7_556 . ? N9 N3 C5 109.53(14) . . ? N9 N3 Cd1 118.27(10) . . ? C5 N3 Cd1 132.19(11) . . ? N7 N1 C2 108.87(15) . . ? N7 N1 Cd1 118.94(11) . . ? C2 N1 Cd1 130.57(12) . . ? N8 N2 C3 109.34(14) . . ? N8 N2 Cd1 121.74(11) . . ? C3 N2 Cd1 128.90(11) . . ? N6 B1 N5 110.57(14) 5_556 2 ? N6 B1 N4 107.00(13) 5_556 . ? N5 B1 N4 108.34(13) 2 . ? N6 B1 H1B 108.6(10) 5_556 . ? N5 B1 H1B 109.6(10) 2 . ? N4 B1 H1B 112.6(10) . . ? N9 N4 C6 109.90(14) . . ? N9 N4 B1 121.83(13) . . ? C6 N4 B1 128.24(14) . . ? N8 N5 C4 110.10(14) . . ? N8 N5 B1 119.01(13) . 2 ? C4 N5 B1 130.84(14) . 2 ? N2 N8 N5 107.15(13) . . ? N7 N6 C1 109.71(14) . . ? N7 N6 B1 121.00(13) . 5_556 ? C1 N6 B1 129.28(15) . 5_556 ? N3 N9 N4 107.22(13) . . ? N1 N7 N6 107.68(13) . . ? N4 C6 C5 106.04(15) . . ? N4 C6 H6 127.0 . . ? C5 C6 H6 127.0 . . ? N3 C5 C6 107.31(15) . . ? N3 C5 H5 126.3 . . ? C6 C5 H5 126.3 . . ? N2 C3 C4 107.74(15) . . ? N2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? N5 C4 C3 105.66(15) . . ? N5 C4 H4 127.2 . . ? C3 C4 H4 127.2 . . ? N1 C2 C1 107.99(16) . . ? N1 C2 H2 126.0 . . ? C1 C2 H2 126.0 . . ? N6 C1 C2 105.75(16) . . ? N6 C1 H1 127.1 . . ? C2 C1 H1 127.1 . . ? 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 N3 Cd1 N3 N9 19(100) 7_556 . . . ? N1 Cd1 N3 N9 -117.27(12) . . . . ? N1 Cd1 N3 N9 62.73(12) 7_556 . . . ? N2 Cd1 N3 N9 149.15(13) 7_556 . . . ? N2 Cd1 N3 N9 -30.85(13) . . . . ? N3 Cd1 N3 C5 -160(100) 7_556 . . . ? N1 Cd1 N3 C5 63.67(16) . . . . ? N1 Cd1 N3 C5 -116.33(16) 7_556 . . . ? N2 Cd1 N3 C5 -29.91(16) 7_556 . . . ? N2 Cd1 N3 C5 150.09(16) . . . . ? N3 Cd1 N1 N7 -175.45(12) 7_556 . . . ? N3 Cd1 N1 N7 4.55(12) . . . . ? N1 Cd1 N1 N7 -161(100) 7_556 . . . ? N2 Cd1 N1 N7 95.06(12) 7_556 . . . ? N2 Cd1 N1 N7 -84.94(12) . . . . ? N3 Cd1 N1 C2 -11.69(17) 7_556 . . . ? N3 Cd1 N1 C2 168.31(17) . . . . ? N1 Cd1 N1 C2 3(100) 7_556 . . . ? N2 Cd1 N1 C2 -101.19(17) 7_556 . . . ? N2 Cd1 N1 C2 78.81(17) . . . . ? N3 Cd1 N2 N8 -39.19(12) 7_556 . . . ? N3 Cd1 N2 N8 140.81(12) . . . . ? N1 Cd1 N2 N8 -127.49(12) . . . . ? N1 Cd1 N2 N8 52.51(12) 7_556 . . . ? N2 Cd1 N2 N8 -116(100) 7_556 . . . ? N3 Cd1 N2 C3 139.08(15) 7_556 . . . ? N3 Cd1 N2 C3 -40.92(15) . . . . ? N1 Cd1 N2 C3 50.78(15) . . . . ? N1 Cd1 N2 C3 -129.22(15) 7_556 . . . ? N2 Cd1 N2 C3 62(100) 7_556 . . . ? N6 B1 N4 N9 136.18(15) 5_556 . . . ? N5 B1 N4 N9 16.9(2) 2 . . . ? N6 B1 N4 C6 -46.2(2) 5_556 . . . ? N5 B1 N4 C6 -165.47(15) 2 . . . ? C3 N2 N8 N5 -0.09(18) . . . . ? Cd1 N2 N8 N5 178.48(10) . . . . ? C4 N5 N8 N2 0.00(18) . . . . ? B1 N5 N8 N2 177.85(13) 2 . . . ? C5 N3 N9 N4 -0.06(19) . . . . ? Cd1 N3 N9 N4 -179.31(10) . . . . ? C6 N4 N9 N3 0.22(18) . . . . ? B1 N4 N9 N3 178.20(14) . . . . ? C2 N1 N7 N6 0.10(19) . . . . ? Cd1 N1 N7 N6 167.12(10) . . . . ? C1 N6 N7 N1 -0.25(19) . . . . ? B1 N6 N7 N1 178.55(14) 5_556 . . . ? N9 N4 C6 C5 -0.29(19) . . . . ? B1 N4 C6 C5 -178.10(15) . . . . ? N9 N3 C5 C6 -0.1(2) . . . . ? Cd1 N3 C5 C6 179.00(12) . . . . ? N4 C6 C5 N3 0.2(2) . . . . ? N8 N2 C3 C4 0.2(2) . . . . ? Cd1 N2 C3 C4 -178.28(12) . . . . ? N8 N5 C4 C3 0.10(19) . . . . ? B1 N5 C4 C3 -177.43(16) 2 . . . ? N2 C3 C4 N5 -0.1(2) . . . . ? N7 N1 C2 C1 0.1(2) . . . . ? Cd1 N1 C2 C1 -164.93(14) . . . . ? N7 N6 C1 C2 0.3(2) . . . . ? B1 N6 C1 C2 -178.38(17) 5_556 . . . ? N1 C2 C1 N6 -0.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 28.51 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.396 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 961785' ####################################################################### # # 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_Ligand _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H7 B N9 Na' _chemical_formula_weight 239.01 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting cubic _symmetry_space_group_name_H-M 'p 43 3 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'z, x, y' 'z+1/2, -x+1/2, -y' '-z+1/2, -x, y+1/2' '-z, x+1/2, -y+1/2' 'y, z, x' '-y, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x' '-y+1/2, -z, x+1/2' 'y+1/4, x+3/4, -z+3/4' '-y+1/4, -x+1/4, -z+1/4' 'y+3/4, -x+3/4, z+1/4' '-y+3/4, x+1/4, z+3/4' 'x+1/4, z+3/4, -y+3/4' '-x+3/4, z+1/4, y+3/4' '-x+1/4, -z+1/4, -y+1/4' 'x+3/4, -z+3/4, y+1/4' 'z+1/4, y+3/4, -x+3/4' 'z+3/4, -y+3/4, x+1/4' '-z+3/4, y+1/4, x+3/4' '-z+1/4, -y+1/4, -x+1/4' _cell_length_a 13.1478(6) _cell_length_b 13.1478(6) _cell_length_c 13.1478(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2272.79(18) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9617 _exptl_absorpt_correction_T_max 0.9806 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4942 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0112 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 26.26 _reflns_number_total 774 _reflns_number_gt 748 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.3906P] 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(5) _refine_ls_number_reflns 774 _refine_ls_number_parameters 54 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0654 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Na1 Na 0.1250 0.1250 0.1250 0.0151(2) Uani 1 6 d S . . N1 N 0.31084(7) 0.16329(7) 0.12890(7) 0.0169(2) Uani 1 1 d . . . N2 N 0.34738(7) 0.23103(7) 0.19669(7) 0.0150(2) Uani 1 1 d . . . N3 N 0.38518(7) 0.13882(8) 0.06602(7) 0.0187(2) Uani 1 1 d . . . C3 C 0.46972(9) 0.19159(9) 0.09366(9) 0.0211(3) Uani 1 1 d . . . H3 H 0.5328 0.1885 0.0618 0.025 Uiso 1 1 calc R . . C2 C 0.44609(9) 0.25008(9) 0.17642(9) 0.0192(3) Uani 1 1 d . . . H2 H 0.4892 0.2939 0.2114 0.023 Uiso 1 1 calc R . . Na2 Na 0.3750 0.1250 -0.1250 0.0179(3) Uani 1 6 d S . . B2 B 0.28050(9) 0.28050(9) 0.28050(9) 0.0155(4) Uani 1 3 d S . . H4 H 0.3285(11) 0.3285(11) 0.3285(11) 0.019 Uiso 1 3 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na1 0.0151(2) 0.0151(2) 0.0151(2) -0.0016(2) -0.0016(2) -0.0016(2) N1 0.0175(5) 0.0170(5) 0.0162(5) -0.0019(4) 0.0000(3) -0.0008(4) N2 0.0149(5) 0.0140(4) 0.0160(4) 0.0006(4) -0.0012(4) -0.0010(3) N3 0.0171(5) 0.0211(5) 0.0178(5) -0.0005(4) 0.0027(4) 0.0011(4) C3 0.0149(5) 0.0262(6) 0.0221(6) 0.0011(5) 0.0026(4) -0.0017(5) C2 0.0146(5) 0.0210(6) 0.0219(6) 0.0016(4) -0.0007(4) -0.0034(4) Na2 0.0179(3) 0.0179(3) 0.0179(3) -0.0018(2) 0.0018(2) -0.0018(2) B2 0.0155(4) 0.0155(4) 0.0155(4) -0.0016(5) -0.0016(5) -0.0016(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 Na1 N1 2.4953(10) 24 ? Na1 N1 2.4953(10) . ? Na1 N1 2.4953(10) 5 ? Na1 N1 2.4953(10) 9 ? Na1 N1 2.4953(10) 14 ? Na1 N1 2.4953(10) 19 ? N1 N3 1.3200(14) . ? N1 N2 1.3486(13) . ? N2 C2 1.3483(15) . ? N2 B2 1.5526(11) . ? N3 C3 1.3598(15) . ? N3 Na2 2.5216(10) . ? C3 C2 1.3682(17) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? Na2 N3 2.5216(10) 24 ? Na2 N3 2.5216(10) 18_554 ? Na2 N3 2.5216(10) 12_554 ? Na2 N3 2.5216(10) 13_544 ? Na2 N3 2.5216(10) 6 ? B2 N2 1.5526(11) 9 ? B2 N2 1.5526(11) 5 ? B2 H4 1.09(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 Na1 N1 94.64(4) 24 . ? N1 Na1 N1 113.30(4) 24 5 ? N1 Na1 N1 77.19(3) . 5 ? N1 Na1 N1 165.28(4) 24 9 ? N1 Na1 N1 77.19(3) . 9 ? N1 Na1 N1 77.19(3) 5 9 ? N1 Na1 N1 77.19(3) 24 14 ? N1 Na1 N1 113.30(4) . 14 ? N1 Na1 N1 165.28(4) 5 14 ? N1 Na1 N1 94.64(4) 9 14 ? N1 Na1 N1 77.19(3) 24 19 ? N1 Na1 N1 165.28(4) . 19 ? N1 Na1 N1 94.64(4) 5 19 ? N1 Na1 N1 113.30(4) 9 19 ? N1 Na1 N1 77.19(3) 14 19 ? N3 N1 N2 108.13(9) . . ? N3 N1 Na1 131.53(7) . . ? N2 N1 Na1 119.71(7) . . ? C2 N2 N1 109.57(9) . . ? C2 N2 B2 127.42(11) . . ? N1 N2 B2 122.96(11) . . ? N1 N3 C3 108.27(9) . . ? N1 N3 Na2 127.02(7) . . ? C3 N3 Na2 110.27(7) . . ? N3 C3 C2 108.28(10) . . ? N3 C3 H3 125.9 . . ? C2 C3 H3 125.9 . . ? N2 C2 C3 105.75(11) . . ? N2 C2 H2 127.1 . . ? C3 C2 H2 127.1 . . ? N3 Na2 N3 96.37(4) 24 . ? N3 Na2 N3 91.30(3) 24 18_554 ? N3 Na2 N3 81.91(5) . 18_554 ? N3 Na2 N3 81.91(5) 24 12_554 ? N3 Na2 N3 91.30(3) . 12_554 ? N3 Na2 N3 169.84(4) 18_554 12_554 ? N3 Na2 N3 91.30(3) 24 13_544 ? N3 Na2 N3 169.84(4) . 13_544 ? N3 Na2 N3 91.30(3) 18_554 13_544 ? N3 Na2 N3 96.37(4) 12_554 13_544 ? N3 Na2 N3 169.84(4) 24 6 ? N3 Na2 N3 91.30(3) . 6 ? N3 Na2 N3 96.37(4) 18_554 6 ? N3 Na2 N3 91.30(3) 12_554 6 ? N3 Na2 N3 81.91(5) 13_544 6 ? N2 B2 N2 110.00(8) . 9 ? N2 B2 N2 110.00(8) . 5 ? N2 B2 N2 110.00(8) 9 5 ? N2 B2 H4 108.9(8) . . ? N2 B2 H4 108.9(8) 9 . ? N2 B2 H4 108.9(8) 5 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.26 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.172 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 961786'