# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jane Nelson' _publ_contact_author_email DRMJNELSON@HOTMAIL.COM _publ_section_title ; A novel trisprotonated Aldiminate Cryptand ; loop_ _publ_author_name 'Jane Nelson' 'Aileen Chin' 'Mark Edgar' 'C. Harding' 'V. McKee' # Attachment '1.cif.cif' data_mimgt _database_code_depnum_ccdc_archive 'CCDC 711459' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H45 Cl3 N8 O3' _chemical_formula_weight 564.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P-6 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x, y, -z' '-y, x-y, -z' '-x+y, -x, -z' _cell_length_a 7.9230(5) _cell_length_b 7.9230(5) _cell_length_c 13.4371(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 730.49(9) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 302 _exptl_absorpt_coefficient_mu 0.350 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9269 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'SADABS v2.03, Sheldrick, G.M., (2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5591 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.66 _reflns_number_total 1228 _reflns_number_gt 1156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0367P)^2^+0.1086P] 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 constr _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 0.43(7) _refine_ls_number_reflns 1228 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0689 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 Cl1 Cl 0.0000 1.0000 0.16448(5) 0.03082(16) Uani 1 3 d S . . Cl2 Cl -0.3333 0.3333 0.5000 0.0321(2) Uani 1 6 d S . . N1 N 0.3333 0.6667 0.30729(15) 0.0203(4) Uani 1 3 d S . . C1 C 0.3672(2) 0.8571(2) 0.34095(10) 0.0255(3) Uani 1 1 d . . . H1A H 0.4216 0.8822 0.4092 0.031 Uiso 1 1 calc R . . H1B H 0.2414 0.8553 0.3432 0.031 Uiso 1 1 calc R . . C2 C 0.5067(2) 1.0202(2) 0.27267(11) 0.0272(3) Uani 1 1 d . . . H2A H 0.5487 1.1474 0.3050 0.033 Uiso 1 1 calc R . . H2B H 0.6239 1.0086 0.2612 0.033 Uiso 1 1 calc R . . N3 N 0.41411(18) 1.01252(19) 0.17710(8) 0.0264(3) Uani 1 1 d . . . C3 C 0.4818(2) 1.0035(3) 0.08953(11) 0.0268(3) Uani 1 1 d . . . C4 C 0.3936(3) 1.0011(3) 0.0000 0.0275(4) Uani 1 2 d S . . O1W O -0.0593(4) 0.7783(4) 0.4631(2) 0.0575(10) Uani 0.50 1 d P . . H3N H 0.3037 1.0070 0.1819 0.040 Uiso 1 1 d . . . H3 H 0.5952 0.9959 0.0886 0.040 Uiso 1 1 d . . . H4 H 0.2738 0.9916 0.0000 0.040 Uiso 1 2 d S . . H1WA H -0.1161 0.8235 0.5000 0.040 Uiso 1 2 d S . . H1WB H -0.1236 0.6600 0.5000 0.040 Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.02709(19) 0.02709(19) 0.0383(3) 0.000 0.000 0.01354(9) Cl2 0.0318(3) 0.0318(3) 0.0326(4) 0.000 0.000 0.01591(14) N1 0.0214(6) 0.0214(6) 0.0182(9) 0.000 0.000 0.0107(3) C1 0.0306(7) 0.0260(7) 0.0213(6) -0.0045(5) -0.0004(6) 0.0150(6) C2 0.0285(7) 0.0212(6) 0.0303(7) -0.0021(7) -0.0040(7) 0.0112(5) N3 0.0253(6) 0.0247(6) 0.0300(6) 0.0018(5) -0.0006(5) 0.0130(5) C3 0.0257(7) 0.0201(6) 0.0342(7) 0.0015(7) 0.0009(6) 0.0111(5) C4 0.0281(10) 0.0228(9) 0.0308(9) 0.000 0.000 0.0120(8) O1W 0.0401(13) 0.0300(12) 0.101(3) -0.0071(13) 0.0118(13) 0.0166(10) _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 N1 C1 1.4655(16) . ? N1 C1 1.4655(16) 2_665 ? N1 C1 1.4655(16) 3_565 ? N1 N1 8.258(4) 4 ? C1 C2 1.518(2) . ? C2 N3 1.4650(18) . ? N3 C3 1.3099(19) . ? C3 C4 1.3865(18) . ? C4 C3 1.3865(18) 4 ? O1W O1W 0.991(6) 4_556 ? 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 C1 N1 C1 110.92(9) . 2_665 ? C1 N1 C1 110.92(9) . 3_565 ? C1 N1 C1 110.92(9) 2_665 3_565 ? C1 N1 N1 107.98(9) . 4 ? C1 N1 N1 107.98(10) 2_665 4 ? C1 N1 N1 107.98(9) 3_565 4 ? N1 C1 C2 111.74(12) . . ? N3 C2 C1 110.98(13) . . ? C3 N3 C2 125.42(13) . . ? N3 C3 C4 124.26(14) . . ? C3 C4 C3 120.4(2) . 4 ? 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 C1 C2 -153.71(14) 2_665 . . . ? C1 N1 C1 C2 82.5(2) 3_565 . . . ? N1 N1 C1 C2 -35.58(13) 4 . . . ? N1 C1 C2 N3 71.44(16) . . . . ? C1 C2 N3 C3 -124.64(16) . . . . ? C2 N3 C3 C4 -178.36(16) . . . . ? N3 C3 C4 C3 176.01(11) . . . 4 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N Cl1 0.86 2.39 3.2370(13) 170.0 . O1W H1WA O1W 0.86 2.13 2.902(5) 148.7 6_466 O1W H1WA O1W 0.86 2.13 2.902(5) 148.7 6_466 O1W H1WB Cl2 0.95 2.27 3.120(3) 148.0 . _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.185 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.038 # Attachment '2a.cif.cif' data_agmimsq _database_code_depnum_ccdc_archive 'CCDC 711460' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H45 N11 O12' _chemical_formula_weight 643.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(3)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 8.4018(5) _cell_length_b 8.4018(5) _cell_length_c 26.022(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1590.78(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5030 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 23.21 _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9762 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details 'SADABS v2007/2, Sheldrick, G.M., (2007)' _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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11497 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 24.99 _reflns_number_total 967 _reflns_number_gt 842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0817P)^2^+3.1216P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.003(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 967 _refine_ls_number_parameters 59 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.2459 _refine_ls_wR_factor_gt 0.2440 _refine_ls_goodness_of_fit_ref 1.289 _refine_ls_restrained_S_all 1.289 _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 N1 N 1.0000 1.0000 0.0949(2) 0.0326(12) Uani 1 3 d S . . C1 C 0.8202(5) 0.8512(5) 0.07673(15) 0.0356(10) Uani 1 1 d . . . H1A H 0.8216 0.7365 0.0768 0.043 Uiso 1 1 calc R . . H1B H 0.8016 0.8768 0.0416 0.043 Uiso 1 1 calc R . . C2 C 0.6609(5) 0.8288(5) 0.10930(16) 0.0374(10) Uani 1 1 d . . . H2A H 0.6726 0.9483 0.1150 0.045 Uiso 1 1 calc R . . H2B H 0.5466 0.7531 0.0910 0.045 Uiso 1 1 calc R . . N3 N 0.6548(4) 0.7440(4) 0.15882(13) 0.0384(9) Uani 1 1 d . . . H3N H 0.6320 0.6321 0.1583 0.046 Uiso 1 1 calc R . . C3 C 0.6807(5) 0.8217(5) 0.20373(15) 0.0361(10) Uani 1 1 d . . . H3 H 0.7094 0.9439 0.2048 0.043 Uiso 1 1 calc R . . C4 C 0.6682(7) 0.7345(7) 0.2500 0.0369(13) Uani 1 2 d S . . H4 H 0.6513 0.6164 0.2500 0.044 Uiso 1 2 calc SR . . O11 O 0.5280(4) 0.3484(4) 0.17072(14) 0.0516(10) Uani 1 1 d . . . N11 N 0.6667 0.3333 0.1706(2) 0.0270(12) Uani 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 N1 0.0261(16) 0.0261(16) 0.045(3) 0.000 0.000 0.0131(8) C1 0.0285(19) 0.0276(19) 0.050(2) -0.0011(16) -0.0012(16) 0.0133(16) C2 0.028(2) 0.0278(19) 0.056(2) 0.0019(17) -0.0043(17) 0.0143(15) N3 0.0337(18) 0.0204(15) 0.063(2) 0.0052(14) 0.0040(15) 0.0150(13) C3 0.0293(19) 0.0215(18) 0.059(2) 0.0001(16) 0.0014(17) 0.0136(15) C4 0.032(3) 0.023(2) 0.059(3) 0.000 0.000 0.016(2) O11 0.0244(15) 0.0291(15) 0.105(3) -0.0030(15) -0.0027(15) 0.0162(12) N11 0.0200(16) 0.0200(16) 0.041(3) 0.000 0.000 0.0100(8) _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 N1 C1 1.476(4) . ? N1 C1 1.476(4) 2_765 ? N1 C1 1.476(4) 3_675 ? C1 C2 1.514(5) . ? C2 N3 1.461(5) . ? N3 C3 1.303(5) . ? C3 C4 1.386(5) . ? C4 C3 1.386(5) 10_556 ? O11 N11 1.233(3) . ? N11 O11 1.233(3) 2_655 ? N11 O11 1.233(3) 3_665 ? 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 C1 N1 C1 110.2(2) . 2_765 ? C1 N1 C1 110.2(2) . 3_675 ? C1 N1 C1 110.2(2) 2_765 3_675 ? N1 C1 C2 113.1(3) . . ? N3 C2 C1 111.6(3) . . ? C3 N3 C2 126.2(3) . . ? N3 C3 C4 124.4(4) . . ? C3 C4 C3 120.7(5) 10_556 . ? O11 N11 O11 119.999(5) 2_655 3_665 ? O11 N11 O11 119.999(5) 2_655 . ? O11 N11 O11 119.999(5) 3_665 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N O11 0.86 2.11 2.956(4) 166.0 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.330 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.079 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 -0.030 0.460 0.500 166.7 62.8 2 -0.028 0.461 1.000 166.8 62.8 _platon_squeeze_details ; Fitted as nitrate + 3 H2O ; # Attachment '3a.cif.cif' data_mimbtoh _database_code_depnum_ccdc_archive 'CCDC 711461' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H52 N8 O4' _chemical_formula_weight 528.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9092(3) _cell_length_b 17.0385(7) _cell_length_c 23.2707(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.0430(10) _cell_angle_gamma 90.00 _cell_volume 3135.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8500 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 25.79 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.120 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9704 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details 'SADABS v2007/2, Sheldrick, G.M., (2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27047 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6153 _reflns_number_gt 4907 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0676P)^2^+0.9193P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6153 _refine_ls_number_parameters 466 _refine_ls_number_restraints 649 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.002 _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 N1 N 0.22428(13) 0.86137(7) -0.01837(4) 0.0305(3) Uani 1 1 d DU . . C11 C 0.3089(2) 0.82283(11) -0.06572(6) 0.0487(4) Uani 1 1 d DU . . H11A H 0.3575 0.8631 -0.0913 0.058 Uiso 1 1 calc R . . H11B H 0.2252 0.7922 -0.0885 0.058 Uiso 1 1 calc R . . C12 C 0.4486(2) 0.76864(11) -0.04431(8) 0.0551(5) Uani 1 1 d DU . . H12A H 0.5171 0.7515 -0.0772 0.066 Uiso 1 1 calc R . . H12B H 0.5237 0.7975 -0.0172 0.066 Uiso 1 1 calc R . . N11 N 0.37991(17) 0.70040(8) -0.01579(7) 0.0560(4) Uani 1 1 d DU . . H11 H 0.3092 0.6694 -0.0346 0.067 Uiso 0.60 1 calc PR . . C13 C 0.4217(2) 0.68456(10) 0.03728(9) 0.0574(5) Uani 1 1 d U . . H13 H 0.4973 0.7194 0.0566 0.069 Uiso 1 1 calc R . . C14 C 0.3628(2) 0.61964(10) 0.06775(10) 0.0611(5) Uani 1 1 d U B . H14 H 0.2819 0.5858 0.0500 0.073 Uiso 1 1 calc R . . C15 C 0.4191(2) 0.60346(10) 0.12270(12) 0.0684(6) Uani 1 1 d U . . H15 H 0.4833 0.6391 0.1457 0.082 Uiso 1 1 calc R A 1 N12 N 0.3766(10) 0.5370(4) 0.1390(2) 0.0432(13) Uani 0.40 1 d PDU B 1 H12 H 0.3050 0.5067 0.1200 0.052 Uiso 0.40 1 calc PR B 1 C16 C 0.4574(7) 0.5151(3) 0.1925(2) 0.0427(12) Uani 0.40 1 d PDU B 1 H16A H 0.5223 0.5602 0.2081 0.051 Uiso 0.40 1 calc PR B 1 H16B H 0.5376 0.4715 0.1859 0.051 Uiso 0.40 1 calc PR B 1 C17 C 0.3269(6) 0.4896(3) 0.2357(2) 0.0412(11) Uani 0.40 1 d PDU B 1 H17A H 0.2471 0.4523 0.2171 0.049 Uiso 0.40 1 calc PR B 1 H17B H 0.3845 0.4620 0.2680 0.049 Uiso 0.40 1 calc PR B 1 N2 N 0.2326(6) 0.5562(3) 0.2581(2) 0.0328(9) Uani 0.40 1 d PDU B 1 N12' N 0.3692(6) 0.5446(3) 0.16178(16) 0.0432(9) Uani 0.60 1 d PDU B 2 C16' C 0.4403(4) 0.5294(2) 0.21905(17) 0.0476(8) Uani 0.60 1 d PDU B 2 H16C H 0.5069 0.5755 0.2320 0.057 Uiso 0.60 1 calc PR B 2 H16D H 0.5176 0.4838 0.2174 0.057 Uiso 0.60 1 calc PR B 2 C17' C 0.3023(5) 0.5128(2) 0.26192(18) 0.0468(8) Uani 0.60 1 d PDU B 2 H17C H 0.2239 0.4729 0.2457 0.056 Uiso 0.60 1 calc PR B 2 H17D H 0.3539 0.4910 0.2976 0.056 Uiso 0.60 1 calc PR B 2 N2' N 0.2075(4) 0.58343(19) 0.27577(13) 0.0378(7) Uani 0.60 1 d PDU B 2 C21 C 0.31332(18) 0.93220(8) 0.00012(6) 0.0378(3) Uani 1 1 d U . . H21A H 0.2740 0.9770 -0.0237 0.045 Uiso 1 1 calc R . . H21B H 0.4359 0.9254 -0.0061 0.045 Uiso 1 1 calc R . . C22 C 0.28502(19) 0.95040(9) 0.06235(7) 0.0430(4) Uani 1 1 d U . . H22A H 0.3198 1.0052 0.0702 0.052 Uiso 1 1 calc R . . H22B H 0.1628 0.9460 0.0703 0.052 Uiso 1 1 calc R . . N21 N 0.37826(15) 0.89842(8) 0.10047(5) 0.0401(3) Uani 1 1 d U . . H21 H 0.4890 0.8968 0.0977 0.048 Uiso 1 1 calc R . . C23 C 0.30656(18) 0.85305(9) 0.13935(6) 0.0405(3) Uani 1 1 d U . . H23 H 0.1866 0.8499 0.1384 0.049 Uiso 1 1 calc R . . C24 C 0.39029(18) 0.81049(9) 0.18066(6) 0.0397(3) Uani 1 1 d U . . H24 H 0.5102 0.8076 0.1801 0.048 Uiso 1 1 calc R . . C25 C 0.3027(2) 0.77095(12) 0.22393(7) 0.0530(4) Uani 1 1 d U . . H25 H 0.1836 0.7773 0.2254 0.064 Uiso 1 1 calc R C 1 N22 N 0.3859(12) 0.7205(3) 0.2669(4) 0.0380(14) Uani 0.40 1 d PDU B 1 C26 C 0.2856(7) 0.6800(4) 0.3100(2) 0.0410(12) Uani 0.40 1 d PDU B 1 H26A H 0.1639 0.6904 0.3028 0.049 Uiso 0.40 1 calc PR B 1 H26B H 0.3161 0.6999 0.3487 0.049 Uiso 0.40 1 calc PR B 1 C27 C 0.3186(6) 0.5924(3) 0.3071(2) 0.0395(11) Uani 0.40 1 d PDU B 1 H27A H 0.4417 0.5831 0.3045 0.047 Uiso 0.40 1 calc PR B 1 H27B H 0.2795 0.5674 0.3430 0.047 Uiso 0.40 1 calc PR B 1 N22' N 0.3674(8) 0.7467(2) 0.2678(3) 0.0410(10) Uani 0.60 1 d PDU B 2 C26' C 0.2605(6) 0.7169(2) 0.31300(16) 0.0496(9) Uani 0.60 1 d PDU B 2 H26C H 0.1403 0.7268 0.3027 0.060 Uiso 0.60 1 calc PR B 2 H26D H 0.2869 0.7449 0.3494 0.060 Uiso 0.60 1 calc PR B 2 C27' C 0.2885(5) 0.6294(3) 0.32135(15) 0.0468(8) Uani 0.60 1 d PDU B 2 H27C H 0.4115 0.6183 0.3221 0.056 Uiso 0.60 1 calc PR B 2 H27D H 0.2427 0.6133 0.3589 0.056 Uiso 0.60 1 calc PR B 2 C31 C 0.04627(17) 0.87667(9) -0.03197(6) 0.0361(3) Uani 1 1 d U . . H31A H 0.0343 0.8918 -0.0729 0.043 Uiso 1 1 calc R . . H31B H 0.0067 0.9212 -0.0084 0.043 Uiso 1 1 calc R . . C32 C -0.06329(17) 0.80524(9) -0.02064(6) 0.0366(3) Uani 1 1 d U . . H32A H -0.1706 0.8100 -0.0429 0.044 Uiso 1 1 calc R . . H32B H -0.0043 0.7575 -0.0339 0.044 Uiso 1 1 calc R . . N31 N -0.10043(14) 0.79711(7) 0.04010(5) 0.0337(3) Uani 1 1 d U . . C33 C -0.05602(16) 0.73386(8) 0.06760(6) 0.0345(3) Uani 1 1 d U . . H33 H 0.0099 0.6961 0.0480 0.041 Uiso 1 1 calc R . . C34 C -0.09979(17) 0.71792(8) 0.12485(6) 0.0360(3) Uani 1 1 d U . . H34 H -0.1594 0.7564 0.1459 0.043 Uiso 1 1 calc R . . C35 C -0.05832(18) 0.64814(9) 0.15083(7) 0.0420(4) Uani 1 1 d U . . H35 H 0.0140 0.6174 0.1277 0.050 Uiso 1 1 calc R D 1 N32 N -0.0896(14) 0.6155(5) 0.1954(4) 0.0377(16) Uani 0.40 1 d PDU B 1 H32 H -0.1437 0.6451 0.2201 0.045 Uiso 0.40 1 calc PR B 1 C36 C -0.0549(10) 0.5367(4) 0.2160(3) 0.0406(15) Uani 0.40 1 d PDU B 1 H36A H 0.0018 0.5067 0.1854 0.049 Uiso 0.40 1 calc PR B 1 H36B H -0.1631 0.5102 0.2241 0.049 Uiso 0.40 1 calc PR B 1 C37 C 0.0563(7) 0.5359(3) 0.2700(2) 0.0431(12) Uani 0.40 1 d PDU B 1 H37A H 0.0109 0.5738 0.2981 0.052 Uiso 0.40 1 calc PR B 1 H37B H 0.0525 0.4830 0.2876 0.052 Uiso 0.40 1 calc PR B 1 N32' N -0.1118(9) 0.6327(3) 0.2072(2) 0.0318(9) Uani 0.60 1 d PDU B 2 H32' H -0.1674 0.6686 0.2264 0.038 Uiso 0.60 1 calc PR B 2 C36' C -0.0746(7) 0.5573(3) 0.23329(19) 0.0394(10) Uani 0.60 1 d PDU B 2 H36C H -0.0132 0.5243 0.2056 0.047 Uiso 0.60 1 calc PR B 2 H36D H -0.1819 0.5305 0.2423 0.047 Uiso 0.60 1 calc PR B 2 C37' C 0.0316(4) 0.5657(2) 0.28791(15) 0.0422(8) Uani 0.60 1 d PDU B 2 H37C H -0.0157 0.6082 0.3117 0.051 Uiso 0.60 1 calc PR B 2 H37D H 0.0260 0.5163 0.3102 0.051 Uiso 0.60 1 calc PR B 2 O45 O 0.1550(13) 0.5780(5) -0.0592(5) 0.081(3) Uani 0.40 1 d PDU E 1 H45 H 0.2189 0.6214 -0.0552 0.050 Uiso 0.40 1 d P F 1 C45 C 0.2320(7) 0.5049(4) -0.0552(3) 0.0797(18) Uani 0.40 1 d PDU E 1 H45A H 0.3374 0.5094 -0.0327 0.120 Uiso 0.40 1 calc PR E 1 H45B H 0.2571 0.4857 -0.0938 0.120 Uiso 0.40 1 calc PR E 1 H45C H 0.1559 0.4680 -0.0363 0.120 Uiso 0.40 1 calc PR E 1 O55 O 0.1415(6) 0.4373(3) 0.1191(2) 0.0644(12) Uani 0.40 1 d PDU G 1 H55 H 0.0682 0.4241 0.0961 0.050 Uiso 0.40 1 d P H 1 C55 C 0.2342(11) 0.3714(4) 0.1143(5) 0.152(5) Uani 0.40 1 d PDU G 1 H55A H 0.1591 0.3267 0.1068 0.228 Uiso 0.40 1 calc PR G 1 H55B H 0.2983 0.3624 0.1501 0.228 Uiso 0.40 1 calc PR G 1 H55C H 0.3128 0.3771 0.0825 0.228 Uiso 0.40 1 calc PR G 1 O41 O 0.1778(7) 0.6001(3) -0.0776(3) 0.0656(12) Uani 0.60 1 d PDU I 2 H41 H 0.0791 0.5809 -0.0910 0.050 Uiso 0.60 1 d P J 2 C41 C 0.2919(6) 0.5419(2) -0.0940(2) 0.0865(13) Uani 0.60 1 d PDU I 2 H41A H 0.3522 0.5593 -0.1282 0.130 Uiso 0.60 1 calc PR I 2 H41B H 0.2302 0.4934 -0.1028 0.130 Uiso 0.60 1 calc PR I 2 H41C H 0.3734 0.5323 -0.0626 0.130 Uiso 0.60 1 calc PR I 2 O51 O 0.1561(5) 0.4278(3) 0.08770(18) 0.0977(14) Uani 0.60 1 d PDU K 2 H51 H 0.1878 0.4577 0.1166 0.050 Uiso 0.60 1 d P L 2 C51 C 0.2334(5) 0.4064(3) 0.0389(3) 0.113(2) Uani 0.60 1 d PDU K 2 H51A H 0.1822 0.4347 0.0062 0.170 Uiso 0.60 1 calc PR K 2 H51B H 0.2200 0.3498 0.0330 0.170 Uiso 0.60 1 calc PR K 2 H51C H 0.3539 0.4193 0.0419 0.170 Uiso 0.60 1 calc PR K 2 O61 O 0.72761(12) 0.90996(6) 0.09553(4) 0.0428(3) Uani 1 1 d DU . . C61 C 0.8174(2) 0.94102(10) 0.14233(7) 0.0501(4) Uani 1 1 d DU . . H61A H 0.8966 0.9810 0.1289 0.075 Uiso 1 1 calc R . . H61B H 0.8805 0.8990 0.1619 0.075 Uiso 1 1 calc R . . H61C H 0.7384 0.9649 0.1691 0.075 Uiso 1 1 calc R . . O71 O 0.71542(17) 0.72791(9) 0.27774(6) 0.0739(4) Uani 1 1 d U . . C71 C 0.7745(3) 0.80208(16) 0.29276(10) 0.0923(8) Uani 1 1 d U . . H71A H 0.7171 0.8202 0.3273 0.139 Uiso 1 1 calc R . . H71B H 0.7515 0.8387 0.2611 0.139 Uiso 1 1 calc R . . H71C H 0.8966 0.7997 0.3004 0.139 Uiso 1 1 calc R . . H61 H 0.7857 0.8747 0.0792 0.050 Uiso 1 1 d . . . H71 H 0.6088 0.7326 0.2739 0.050 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 N1 0.0269(5) 0.0390(6) 0.0255(5) 0.0027(4) -0.0005(4) -0.0038(4) C11 0.0404(8) 0.0799(12) 0.0260(7) -0.0077(7) 0.0048(6) -0.0078(8) C12 0.0345(8) 0.0756(12) 0.0558(10) -0.0270(9) 0.0113(7) -0.0003(8) N11 0.0334(7) 0.0488(8) 0.0856(11) -0.0314(8) -0.0018(7) 0.0030(6) C13 0.0308(8) 0.0459(9) 0.0954(14) -0.0345(9) -0.0050(8) 0.0069(7) C14 0.0324(8) 0.0348(8) 0.1157(16) -0.0199(9) -0.0078(9) 0.0042(7) C15 0.0311(8) 0.0347(9) 0.1388(19) -0.0080(10) -0.0109(10) 0.0044(7) N12 0.040(2) 0.043(3) 0.047(3) -0.012(2) -0.007(3) 0.0039(17) C16 0.030(2) 0.044(3) 0.053(3) -0.008(2) -0.007(2) 0.0045(19) C17 0.037(2) 0.036(3) 0.051(3) 0.010(2) -0.007(2) 0.0053(19) N2 0.0274(19) 0.035(3) 0.036(3) 0.0074(17) -0.0035(16) -0.0006(19) N12' 0.0319(14) 0.0373(15) 0.060(2) -0.0136(19) -0.004(2) -0.0003(11) C16' 0.0314(16) 0.0435(19) 0.068(2) 0.0044(18) -0.0101(17) 0.0050(13) C17' 0.0350(17) 0.041(2) 0.063(2) 0.0192(17) -0.0130(17) -0.0042(15) N2' 0.0337(14) 0.0437(19) 0.0356(17) 0.0111(11) -0.0071(12) -0.0039(13) C21 0.0345(7) 0.0350(7) 0.0436(8) 0.0129(6) -0.0044(6) -0.0074(6) C22 0.0391(8) 0.0352(7) 0.0544(9) -0.0106(7) -0.0102(7) 0.0047(6) N21 0.0310(6) 0.0560(8) 0.0331(6) -0.0073(5) -0.0038(5) 0.0051(5) C23 0.0282(7) 0.0547(9) 0.0385(8) -0.0205(7) -0.0007(6) -0.0011(6) C24 0.0321(7) 0.0523(9) 0.0346(7) -0.0113(6) 0.0001(6) -0.0057(6) C25 0.0385(8) 0.0842(13) 0.0363(8) -0.0140(8) 0.0031(7) -0.0143(8) N22 0.052(3) 0.027(3) 0.035(2) -0.002(2) 0.0000(17) -0.003(3) C26 0.052(3) 0.041(3) 0.029(2) 0.002(3) 0.0038(17) 0.001(3) C27 0.044(2) 0.045(3) 0.030(2) 0.0118(18) -0.0055(18) 0.000(2) N22' 0.049(2) 0.039(2) 0.0350(15) 0.002(2) 0.0024(12) -0.009(2) C26' 0.064(2) 0.054(2) 0.0316(15) 0.0022(18) 0.0030(14) -0.015(2) C27' 0.0486(19) 0.060(3) 0.0313(18) 0.0158(17) -0.0116(13) -0.0139(19) C31 0.0307(7) 0.0472(8) 0.0301(7) 0.0121(6) -0.0050(5) -0.0026(6) C32 0.0308(7) 0.0507(8) 0.0282(7) 0.0009(6) -0.0033(5) -0.0081(6) N31 0.0324(6) 0.0392(6) 0.0294(6) 0.0032(5) 0.0002(5) -0.0070(5) C33 0.0266(6) 0.0387(7) 0.0382(7) -0.0030(6) -0.0019(5) -0.0045(5) C34 0.0304(7) 0.0407(8) 0.0367(7) 0.0046(6) -0.0025(6) -0.0038(6) C35 0.0285(7) 0.0508(9) 0.0463(9) 0.0110(7) -0.0090(6) -0.0083(6) N32 0.031(3) 0.043(3) 0.039(4) 0.000(2) 0.001(2) 0.005(2) C36 0.029(3) 0.039(3) 0.053(4) 0.015(3) -0.010(3) -0.005(2) C37 0.039(2) 0.046(3) 0.044(3) 0.017(2) 0.003(2) -0.002(2) N32' 0.0298(18) 0.040(2) 0.0259(18) 0.0057(15) 0.0017(14) 0.0062(15) C36' 0.0320(17) 0.042(3) 0.044(2) 0.0127(16) -0.0050(16) -0.0057(16) C37' 0.0356(15) 0.056(2) 0.0345(18) 0.0197(14) -0.0029(13) -0.0078(15) O45 0.064(4) 0.075(4) 0.104(7) -0.021(3) -0.037(4) 0.003(3) C45 0.055(3) 0.082(4) 0.101(5) -0.045(4) -0.018(3) 0.014(3) O55 0.045(2) 0.0463(19) 0.101(4) 0.000(2) -0.030(3) -0.0110(15) C55 0.115(6) 0.050(3) 0.288(13) -0.055(5) -0.109(8) 0.020(4) O41 0.0367(14) 0.068(3) 0.092(4) -0.026(2) -0.0150(18) -0.0010(17) C41 0.075(3) 0.061(2) 0.122(4) -0.039(2) -0.030(3) 0.014(2) O51 0.0577(18) 0.127(3) 0.108(3) -0.016(3) -0.011(2) -0.0414(19) C51 0.060(2) 0.072(3) 0.210(6) -0.073(3) 0.031(3) -0.017(2) O61 0.0318(5) 0.0496(6) 0.0471(6) 0.0005(5) -0.0002(4) 0.0087(4) C61 0.0458(9) 0.0561(10) 0.0482(9) -0.0044(7) -0.0017(7) 0.0035(7) O71 0.0470(7) 0.0922(11) 0.0825(10) 0.0242(8) -0.0004(7) 0.0000(7) C71 0.0834(16) 0.124(2) 0.0689(14) 0.0281(14) -0.0265(12) -0.0516(15) _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 N1 C11 1.4561(18) . ? N1 C21 1.4583(17) . ? N1 C31 1.4608(17) . ? C11 C12 1.517(2) . ? C12 N11 1.449(2) . ? N11 C13 1.301(3) . ? C13 C14 1.398(3) . ? C14 C15 1.374(3) . ? C15 N12 1.243(8) . ? C15 N12' 1.415(5) . ? N12 C16 1.439(7) . ? C16 C17 1.517(7) . ? C17 N2 1.460(6) . ? N2 C27 1.455(6) . ? N2 C37 1.468(6) . ? N12' C16' 1.460(5) . ? C16' C17' 1.518(5) . ? C17' N2' 1.457(4) . ? N2' C37' 1.456(4) . ? N2' C27' 1.457(4) . ? C21 C22 1.502(2) . ? C22 N21 1.4461(19) . ? N21 C23 1.325(2) . ? C23 C24 1.366(2) . ? C24 C25 1.404(2) . ? C25 N22' 1.205(6) . ? C25 N22 1.465(8) . ? N22 C26 1.463(9) . ? C26 C27 1.517(6) . ? N22' C26' 1.454(6) . ? C26' C27' 1.520(5) . ? C31 C32 1.5198(19) . ? C32 N31 1.4556(17) . ? N31 C33 1.2985(18) . ? C33 C34 1.409(2) . ? C34 C35 1.371(2) . ? C35 N32 1.207(9) . ? C35 N32' 1.410(6) . ? N32 C36 1.450(9) . ? C36 C37 1.521(8) . ? N32' C36' 1.448(6) . ? C36' C37' 1.517(5) . ? O45 C45 1.389(9) . ? O55 C55 1.347(8) . ? O41 C41 1.399(6) . ? O51 C51 1.350(6) . ? O61 C61 1.3939(19) . ? O71 C71 1.390(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 C11 N1 C21 111.73(11) . . ? C11 N1 C31 111.79(11) . . ? C21 N1 C31 112.00(11) . . ? N1 C11 C12 111.59(12) . . ? N11 C12 C11 111.23(13) . . ? C13 N11 C12 120.68(15) . . ? N11 C13 C14 124.34(16) . . ? C15 C14 C13 121.69(17) . . ? N12 C15 C14 112.5(3) . . ? N12 C15 N12' 22.7(2) . . ? C14 C15 N12' 130.6(2) . . ? C15 N12 C16 112.5(6) . . ? N12 C16 C17 110.5(5) . . ? N2 C17 C16 111.8(4) . . ? C27 N2 C17 112.0(4) . . ? C27 N2 C37 112.6(4) . . ? C17 N2 C37 112.2(4) . . ? C15 N12' C16' 127.3(4) . . ? N12' C16' C17' 111.3(3) . . ? N2' C17' C16' 111.8(3) . . ? C37' N2' C27' 112.3(3) . . ? C37' N2' C17' 111.7(3) . . ? C27' N2' C17' 112.5(3) . . ? N1 C21 C22 112.07(11) . . ? N21 C22 C21 112.45(12) . . ? C23 N21 C22 123.79(13) . . ? N21 C23 C24 125.61(13) . . ? C23 C24 C25 121.35(14) . . ? N22' C25 C24 124.3(3) . . ? N22' C25 N22 17.0(4) . . ? C24 C25 N22 123.3(4) . . ? C26 N22 C25 120.1(7) . . ? N22 C26 C27 109.8(4) . . ? N2 C27 C26 111.9(4) . . ? C25 N22' C26' 119.3(5) . . ? N22' C26' C27' 110.5(3) . . ? N2' C27' C26' 111.9(3) . . ? N1 C31 C32 111.70(11) . . ? N31 C32 C31 111.75(11) . . ? C33 N31 C32 120.01(12) . . ? N31 C33 C34 123.86(13) . . ? C35 C34 C33 121.55(14) . . ? N32 C35 C34 136.7(3) . . ? N32 C35 N32' 17.2(4) . . ? C34 C35 N32' 119.9(2) . . ? C35 N32 C36 132.0(5) . . ? N32 C36 C37 112.6(7) . . ? N2 C37 C36 112.3(5) . . ? C35 N32' C36' 119.6(3) . . ? N32' C36' C37' 111.9(4) . . ? N2' C37' C36' 111.9(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O41 0.88 1.85 2.732(7) 174.6 . N12 H12 O55 0.88 1.75 2.555(9) 150.4 . O41 H41 O51 0.90 1.87 2.689(7) 151.0 3_565 O51 H51 N12' 0.88 2.30 3.110(5) 153.1 . O45 H45 N11 0.90 2.06 2.910(11) 158.0 . O55 H55 O45 0.81 1.95 2.718(12) 157.5 3_565 N21 H21 O61 0.88 1.90 2.7745(16) 171.1 . N32 H32 O71 0.88 2.26 3.134(6) 175.5 1_455 N32' H32' O71 0.88 1.83 2.698(4) 168.3 1_455 O61 H61 N31 0.85 1.85 2.6972(16) 176.0 1_655 O71 H71 N22 0.85 1.78 2.617(10) 167.9 . O71 H71 N22' 0.85 1.93 2.777(6) 177.5 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.265 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.037 # Attachment 'jmim3.cif' data_jmim3 _database_code_depnum_ccdc_archive 'CCDC 711462' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H64 N8 O14' _chemical_formula_weight 652.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P-6c2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x, y, -z+1/2' '-y, x-y, -z+1/2' '-x+y, -x, -z+1/2' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' '-y, -x, -z' '-x+y, y, -z' 'x, x-y, -z' _cell_length_a 8.0397(9) _cell_length_b 8.0397(9) _cell_length_c 33.925(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1899.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4216 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 24.77 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9448 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details ? _exptl_special_details 'SADABS v2008/1, Sheldrick, G.M., (2008)' _diffrn_ambient_temperature 150(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 scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13476 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0129 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1161 _reflns_number_gt 1044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0984P)^2^+1.6040P] 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 1(4) _refine_ls_number_reflns 1161 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.2018 _refine_ls_wR_factor_gt 0.1941 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.002 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 N1 N 0.3333 0.6667 0.12348(13) 0.0428(10) Uani 1 3 d S . . C1 C 0.3223(7) 0.4863(5) 0.11206(9) 0.0501(8) Uani 1 1 d . B . H1A H 0.3853 0.5025 0.0861 0.044(9) Uiso 1 1 calc R . . H1B H 0.1859 0.3853 0.1093 0.053(10) Uiso 1 1 calc R . . C2 C 0.4178(8) 0.4242(7) 0.14200(10) 0.0685(13) Uani 1 1 d . . . H2A H 0.4240 0.3117 0.1320 0.092(15) Uiso 1 1 calc R A 1 H2B H 0.5506 0.5296 0.1468 0.084(16) Uiso 1 1 calc R A 1 N2 N 0.3086(8) 0.3743(7) 0.17852(8) 0.0848(13) Uani 0.50 1 d P B 1 H2 H 0.2107 0.2508 0.1760 0.102 Uiso 0.50 1 d P C 1 N2' N 0.3086(8) 0.3743(7) 0.17852(8) 0.0848(13) Uani 0.50 1 d P B 2 H2' H 0.1850 0.3351 0.1778 0.110 Uiso 0.50 1 calc PR B 2 C3 C 0.3934(10) 0.3870(8) 0.21318(10) 0.0904(19) Uani 1 1 d . . . H3 H 0.5259 0.4251 0.2137 0.051(11) Uiso 1 1 calc R B 1 C4 C 0.2878(9) 0.3440(9) 0.2500 0.0621(15) Uani 1 2 d S . . H4 H 0.1521 0.2887 0.2500 0.11(3) Uiso 1 2 calc SR . . O1W O 0.0000 0.0000 0.15948(11) 0.0799(15) Uani 1 3 d S . . H1WA H 0.0000 0.0000 0.1347 0.104 Uiso 1 3 d S . . O2W O 0.0000 0.0000 0.07872(12) 0.0567(11) Uani 1 3 d S . . H2WA H -0.0186 0.0907 0.0714 0.074 Uiso 0.33 1 d P . . H2WB H 0.1133 0.0313 0.0714 0.074 Uiso 0.33 1 d P . . O3W O -0.2461(5) -0.3167(6) 0.03481(7) 0.0782(10) Uani 1 1 d . . . H3WA H -0.3550 -0.3510 0.0250 0.102 Uiso 0.50 1 d P . . H3WB H -0.1680 -0.2880 0.0164 0.102 Uiso 0.50 1 d P . . H3WC H -0.2500 -0.4060 0.0480 0.102 Uiso 0.50 1 d P . . H3WD H -0.2130 -0.2220 0.0490 0.102 Uiso 0.50 1 d P . . O4W O -0.3333 -0.6667 0.06618(13) 0.0712(14) Uani 1 3 d S . . H4WB H -0.3300 -0.5660 0.0580 0.093 Uiso 0.50 1 d P . . O5W O -0.5050(12) -0.3371(17) -0.00823(18) 0.068(2) Uani 0.33 1 d P . . H5WA H -0.4788 -0.3024 -0.0334 0.088 Uiso 0.33 1 d P . . H5WB H -0.6235 -0.3731 -0.0066 0.088 Uiso 0.33 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0340(12) 0.0340(12) 0.060(3) 0.000 0.000 0.0170(6) C1 0.059(2) 0.0396(18) 0.0526(17) -0.0039(14) -0.0018(17) 0.0255(18) C2 0.109(4) 0.076(3) 0.057(2) 0.0016(18) 0.008(2) 0.074(3) N2 0.087(3) 0.110(3) 0.0453(16) 0.0071(18) 0.0082(18) 0.040(3) N2' 0.087(3) 0.110(3) 0.0453(16) 0.0071(18) 0.0082(18) 0.040(3) C3 0.140(6) 0.105(4) 0.056(2) 0.005(2) -0.004(3) 0.083(4) C4 0.083(5) 0.068(3) 0.046(2) 0.000 0.000 0.045(4) O1W 0.102(2) 0.102(2) 0.0355(19) 0.000 0.000 0.0510(12) O2W 0.0621(16) 0.0621(16) 0.0458(19) 0.000 0.000 0.0310(8) O3W 0.092(2) 0.082(2) 0.0489(13) -0.0054(16) 0.0009(14) 0.034(2) O4W 0.083(2) 0.083(2) 0.048(2) 0.000 0.000 0.0415(11) O5W 0.061(5) 0.097(6) 0.048(4) -0.003(4) -0.003(3) 0.042(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 N1 C1 1.460(3) 3_565 ? N1 C1 1.460(3) 2_665 ? N1 C1 1.460(3) . ? C1 C2 1.502(5) . ? C2 N2 1.454(5) . ? N2 C3 1.337(6) . ? C3 C4 1.452(6) . ? C4 C3 1.452(6) 4 ? O5W O5W 1.39(2) 10_445 ? O5W O5W 1.47(2) 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 C1 N1 C1 113.23(17) 3_565 2_665 ? C1 N1 C1 113.23(17) 3_565 . ? C1 N1 C1 113.23(17) 2_665 . ? N1 C1 C2 111.3(3) . . ? N2 C2 C1 109.2(4) . . ? C3 N2 C2 120.9(5) . . ? N2 C3 C4 121.6(6) . . ? C3 C4 C3 118.8(7) 4 . ? O5W O5W O5W 105.7(5) 10_445 12 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1W 0.91 1.96 2.857(5) 168.3 . O1W H1WA O2W 0.84 1.90 2.740(5) 180.0 . O2W H2WA O3W 0.85 1.95 2.753(4) 157.1 3 O2W H2WB O3W 0.85 1.95 2.753(4) 157.1 2 O3W H3WA O5W 0.84 1.69 2.480(8) 153.8 . O3W H3WA O5W 0.84 2.22 3.048(12) 167.4 10_445 O3W H3WA O5W 0.84 2.39 3.011(12) 130.7 12 O3W H3WB O3W 0.83 1.97 2.752(5) 157.0 11 O3W H3WC O4W 0.83 1.95 2.751(4) 159.9 . O3W H3WD O2W 0.82 2.02 2.753(4) 147.9 . O4W H4WB O3W 0.84 1.93 2.751(4) 162.9 . O5W H5WB O5W 0.85 1.91 2.689(15) 152.8 11_455 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.455 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.048 # Attachment '7a.cif.cif' data_curmgt _database_code_depnum_ccdc_archive 'CCDC 711463' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H52 Cl3 Cu2 N9 O13' _chemical_formula_weight 896.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.1968(6) _cell_length_b 8.8464(5) _cell_length_c 16.3784(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.7790(10) _cell_angle_gamma 90.00 _cell_volume 1766.34(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11058 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 29.1 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 1.505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8058 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details 'SADABS v2.03, Sheldrick, G.M., (2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68800 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11848 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7898 _reflns_number_gt 7081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0680P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.024(11) _refine_ls_number_reflns 7898 _refine_ls_number_parameters 452 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 Cu1 Cu 0.08037(3) 0.89381(5) 0.27290(2) 0.01828(10) Uani 1 1 d . . . Cu2 Cu 0.34861(3) 0.98273(5) 0.17702(2) 0.01817(10) Uani 1 1 d . . . N1 N -0.0678(3) 0.8780(4) 0.32810(19) 0.0230(7) Uani 1 1 d . . . C1A C -0.1464(3) 0.8140(6) 0.2659(3) 0.0298(9) Uani 1 1 d . . . H1A1 H -0.2223 0.8418 0.2797 0.036 Uiso 1 1 calc R . . H1A2 H -0.1409 0.7023 0.2660 0.036 Uiso 1 1 calc R . . C2A C -0.1216(3) 0.8739(5) 0.1815(2) 0.0273(8) Uani 1 1 d . . . H2A1 H -0.1719 0.8278 0.1400 0.033 Uiso 1 1 calc R . . H2A2 H -0.1315 0.9849 0.1798 0.033 Uiso 1 1 calc R . . N3A N -0.0068(3) 0.8344(4) 0.16452(19) 0.0226(7) Uani 1 1 d . . . H3A H -0.0036 0.7297 0.1601 0.027 Uiso 1 1 calc R . . C3A C 0.0336(3) 0.8983(5) 0.0861(2) 0.0241(7) Uani 1 1 d . . . H3A1 H -0.0256 0.8911 0.0435 0.029 Uiso 1 1 calc R . . H3A2 H 0.0962 0.8369 0.0679 0.029 Uiso 1 1 calc R . . C4A C 0.0696(3) 1.0622(5) 0.0945(2) 0.0254(8) Uani 1 1 d . . . H4A1 H 0.0061 1.1278 0.0801 0.030 Uiso 1 1 calc R . . H4A2 H 0.0903 1.0816 0.1524 0.030 Uiso 1 1 calc R . . C5A C 0.1647(3) 1.1079(5) 0.0424(2) 0.0255(8) Uani 1 1 d . . . H5A1 H 0.1432 1.0920 -0.0157 0.031 Uiso 1 1 calc R . . H5A2 H 0.1786 1.2172 0.0502 0.031 Uiso 1 1 calc R . . N4A N 0.2688(3) 1.0238(4) 0.06064(19) 0.0215(7) Uani 1 1 d . . . H4A H 0.2537 0.9272 0.0410 0.026 Uiso 1 1 calc R . . C6A C 0.3544(3) 1.0795(5) 0.0058(2) 0.0265(8) Uani 1 1 d . . . H6A1 H 0.3594 1.1910 0.0094 0.032 Uiso 1 1 calc R . . H6A2 H 0.3348 1.0521 -0.0514 0.032 Uiso 1 1 calc R . . C7A C 0.4636(3) 1.0100(5) 0.0303(2) 0.0266(9) Uani 1 1 d . . . H7A1 H 0.4612 0.8996 0.0203 0.032 Uiso 1 1 calc R . . H7A2 H 0.5219 1.0537 -0.0031 0.032 Uiso 1 1 calc R . . N2 N 0.4891(3) 1.0395(4) 0.11907(19) 0.0202(6) Uani 1 1 d . . . C1B C -0.1027(3) 1.0306(5) 0.3560(3) 0.0261(8) Uani 1 1 d . . . H1B1 H -0.1463 1.0203 0.4057 0.031 Uiso 1 1 calc R . . H1B2 H -0.1498 1.0785 0.3130 0.031 Uiso 1 1 calc R . . C2B C -0.0042(3) 1.1296(5) 0.3744(2) 0.0244(8) Uani 1 1 d . . . H2B1 H -0.0277 1.2324 0.3902 0.029 Uiso 1 1 calc R . . H2B2 H 0.0414 1.0863 0.4196 0.029 Uiso 1 1 calc R . . N3B N 0.0581(3) 1.1353(4) 0.2989(2) 0.0214(6) Uani 1 1 d . . . H3B H 0.0104 1.1725 0.2583 0.026 Uiso 1 1 calc R . . C3B C 0.1541(3) 1.2369(5) 0.3015(3) 0.0260(8) Uani 1 1 d . . . H3B1 H 0.1328 1.3353 0.3251 0.031 Uiso 1 1 calc R . . H3B2 H 0.1780 1.2553 0.2452 0.031 Uiso 1 1 calc R . . C4B C 0.2499(3) 1.1712(5) 0.3523(2) 0.0238(8) Uani 1 1 d . . . H4B1 H 0.2388 1.1939 0.4107 0.029 Uiso 1 1 calc R . . H4B2 H 0.2500 1.0599 0.3459 0.029 Uiso 1 1 calc R . . C5B C 0.3606(3) 1.2326(5) 0.3285(2) 0.0249(8) Uani 1 1 d . . . H5B1 H 0.3632 1.3427 0.3394 0.030 Uiso 1 1 calc R . . H5B2 H 0.4190 1.1839 0.3626 0.030 Uiso 1 1 calc R . . N4B N 0.3819(3) 1.2052(4) 0.24106(19) 0.0209(6) Uani 1 1 d . . . H4B H 0.3390 1.2758 0.2126 0.025 Uiso 1 1 calc R . . C6B C 0.4953(3) 1.2424(5) 0.2219(2) 0.0232(8) Uani 1 1 d . . . H6B1 H 0.5464 1.1859 0.2588 0.028 Uiso 1 1 calc R . . H6B2 H 0.5083 1.3518 0.2305 0.028 Uiso 1 1 calc R . . C7B C 0.5167(3) 1.2016(5) 0.1338(2) 0.0248(8) Uani 1 1 d . . . H7B1 H 0.4714 1.2662 0.0967 0.030 Uiso 1 1 calc R . . H7B2 H 0.5948 1.2197 0.1224 0.030 Uiso 1 1 calc R . . C1C C -0.0544(4) 0.7749(5) 0.3995(3) 0.0281(9) Uani 1 1 d . . . H1C1 H -0.1248 0.7235 0.4094 0.034 Uiso 1 1 calc R . . H1C2 H -0.0335 0.8342 0.4488 0.034 Uiso 1 1 calc R . . C2C C 0.0325(3) 0.6594(5) 0.3837(3) 0.0279(9) Uani 1 1 d . . . H2C1 H 0.0456 0.5957 0.4328 0.034 Uiso 1 1 calc R . . H2C2 H 0.0091 0.5932 0.3376 0.034 Uiso 1 1 calc R . . N3C N 0.1339(3) 0.7427(4) 0.3637(2) 0.0242(7) Uani 1 1 d . . . H3C H 0.1552 0.7992 0.4093 0.029 Uiso 1 1 calc R . . C3C C 0.2259(3) 0.6410(5) 0.3448(3) 0.0265(9) Uani 1 1 d . . . H3C1 H 0.2140 0.5987 0.2893 0.032 Uiso 1 1 calc R . . H3C2 H 0.2279 0.5558 0.3840 0.032 Uiso 1 1 calc R . . C4C C 0.3359(3) 0.7245(5) 0.3495(2) 0.0236(8) Uani 1 1 d . . . H4C1 H 0.3216 0.8346 0.3514 0.028 Uiso 1 1 calc R . . H4C2 H 0.3754 0.6961 0.4009 0.028 Uiso 1 1 calc R . . C5C C 0.4093(4) 0.6916(5) 0.2782(3) 0.0271(8) Uani 1 1 d . . . H5C1 H 0.4715 0.6278 0.2975 0.033 Uiso 1 1 calc R . . H5C2 H 0.3670 0.6339 0.2361 0.033 Uiso 1 1 calc R . . N4C N 0.4526(3) 0.8312(4) 0.24104(19) 0.0222(6) Uani 1 1 d . . . H4C H 0.4872 0.8859 0.2829 0.027 Uiso 1 1 calc R . . C6C C 0.5372(3) 0.7941(5) 0.1818(3) 0.0261(8) Uani 1 1 d . . . H6C1 H 0.5051 0.7323 0.1367 0.031 Uiso 1 1 calc R . . H6C2 H 0.5973 0.7359 0.2088 0.031 Uiso 1 1 calc R . . C7C C 0.5811(3) 0.9428(5) 0.1485(3) 0.0255(8) Uani 1 1 d . . . H7C1 H 0.6238 0.9962 0.1921 0.031 Uiso 1 1 calc R . . H7C2 H 0.6305 0.9220 0.1031 0.031 Uiso 1 1 calc R . . O1 O 0.21729(19) 0.8948(3) 0.21729(14) 0.0198(5) Uani 1 1 d . . . H1 H 0.2229 0.7929 0.1997 0.024 Uiso 1 1 calc R . . Cl1 Cl 0.24854(8) 0.55053(10) 0.07765(6) 0.02371(19) Uani 1 1 d . . . O11 O 0.2102(3) 0.5015(5) -0.0002(2) 0.0507(10) Uani 1 1 d . . . O12 O 0.3092(3) 0.6895(4) 0.0698(2) 0.0396(8) Uani 1 1 d . . . O13 O 0.3203(3) 0.4385(4) 0.1131(2) 0.0428(8) Uani 1 1 d . . . O14 O 0.1614(3) 0.5773(5) 0.1317(3) 0.0565(11) Uani 1 1 d . . . Cl2 Cl 0.82271(9) 0.38665(16) 0.17976(6) 0.0386(2) Uani 1 1 d . . . O21 O 0.7392(3) 0.4947(5) 0.1916(2) 0.0523(10) Uani 1 1 d . . . O22 O 0.8211(5) 0.3378(6) 0.0970(3) 0.0843(17) Uani 1 1 d . . . O23 O 0.9219(5) 0.4344(12) 0.2024(7) 0.215(6) Uani 1 1 d . . . O24 O 0.7945(10) 0.2554(9) 0.2219(5) 0.167(4) Uani 1 1 d . . . Cl3 Cl 0.38402(8) 1.41171(17) 0.56360(6) 0.0386(3) Uani 1 1 d . . . O31 O 0.2990(4) 1.4554(9) 0.5118(2) 0.094(2) Uani 1 1 d . . . O32 O 0.4841(5) 1.4167(12) 0.5291(4) 0.143(4) Uani 1 1 d . . . O33 O 0.3607(8) 1.2612(8) 0.5871(6) 0.141(3) Uani 1 1 d . . . O34 O 0.3827(4) 1.4865(7) 0.6393(3) 0.0736(14) Uani 1 1 d . . . N21 N 0.1651(3) 0.9245(5) 0.5258(2) 0.0421(10) Uani 1 1 d . . . C22 C 0.2438(4) 0.9157(6) 0.5621(2) 0.0337(10) Uani 1 1 d . . . C23 C 0.3463(4) 0.8997(9) 0.6088(3) 0.0542(14) Uani 1 1 d . . . H23A H 0.3315 0.8596 0.6631 0.081 Uiso 1 1 calc R . . H23B H 0.3820 0.9986 0.6143 0.081 Uiso 1 1 calc R . . H23C H 0.3947 0.8300 0.5805 0.081 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01575(19) 0.0194(2) 0.01970(19) 0.00037(18) 0.00094(15) -0.00023(18) Cu2 0.0160(2) 0.0190(2) 0.0195(2) 0.00018(18) 0.00056(15) 0.00020(17) N1 0.0220(15) 0.0233(18) 0.0235(14) -0.0021(14) 0.0001(12) -0.0010(14) C1A 0.0167(18) 0.042(3) 0.031(2) -0.0061(18) 0.0010(15) -0.0061(17) C2A 0.0168(16) 0.035(2) 0.0295(18) -0.0032(17) -0.0020(13) -0.0007(16) N3A 0.0194(15) 0.0236(17) 0.0247(15) -0.0004(13) 0.0012(12) 0.0026(12) C3A 0.0203(16) 0.030(2) 0.0212(16) -0.0003(17) -0.0028(13) 0.0017(17) C4A 0.027(2) 0.026(2) 0.0230(18) 0.0042(16) -0.0023(15) 0.0074(16) C5A 0.027(2) 0.022(2) 0.0270(19) 0.0026(16) -0.0026(15) 0.0046(15) N4A 0.0204(15) 0.0229(18) 0.0211(15) 0.0001(12) 0.0014(12) -0.0001(12) C6A 0.028(2) 0.032(2) 0.0199(17) 0.0013(16) 0.0032(15) -0.0065(17) C7A 0.0255(19) 0.035(3) 0.0194(17) -0.0056(15) 0.0044(14) -0.0042(16) N2 0.0178(15) 0.0202(16) 0.0227(15) -0.0004(12) 0.0011(12) -0.0006(12) C1B 0.0225(19) 0.027(2) 0.029(2) 0.0002(16) 0.0053(15) 0.0017(15) C2B 0.0226(19) 0.024(2) 0.0261(19) -0.0044(16) 0.0030(15) 0.0012(15) N3B 0.0172(15) 0.0234(17) 0.0236(15) 0.0003(13) 0.0011(12) -0.0008(12) C3B 0.025(2) 0.0185(19) 0.035(2) -0.0002(16) 0.0021(16) -0.0019(15) C4B 0.028(2) 0.023(2) 0.0208(17) -0.0024(15) -0.0011(15) -0.0037(15) C5B 0.025(2) 0.027(2) 0.0227(18) -0.0069(16) 0.0010(15) -0.0026(16) N4B 0.0218(15) 0.0222(17) 0.0186(14) 0.0005(12) 0.0003(12) -0.0008(13) C6B 0.0207(18) 0.023(2) 0.0254(18) -0.0014(15) -0.0009(15) -0.0023(15) C7B 0.0206(18) 0.024(2) 0.030(2) 0.0028(16) 0.0004(15) -0.0039(15) C1C 0.030(2) 0.028(2) 0.027(2) 0.0024(16) 0.0076(16) -0.0070(17) C2C 0.025(2) 0.025(2) 0.035(2) 0.0058(17) 0.0004(17) -0.0043(16) N3C 0.0252(17) 0.0232(17) 0.0242(16) 0.0037(13) 0.0011(13) -0.0016(13) C3C 0.025(2) 0.022(2) 0.033(2) 0.0057(16) -0.0019(17) 0.0011(16) C4C 0.0259(19) 0.023(2) 0.0222(17) 0.0050(15) -0.0042(15) -0.0008(15) C5C 0.030(2) 0.018(2) 0.033(2) 0.0024(16) -0.0038(17) 0.0032(16) N4C 0.0209(15) 0.0211(16) 0.0245(15) -0.0015(13) -0.0006(12) 0.0000(12) C6C 0.0190(18) 0.024(2) 0.036(2) -0.0024(17) 0.0003(16) 0.0059(15) C7C 0.0166(17) 0.029(2) 0.0314(19) -0.0024(15) 0.0025(14) 0.0049(14) O1 0.0168(11) 0.0211(13) 0.0214(11) 0.0006(12) 0.0003(9) -0.0001(12) Cl1 0.0260(4) 0.0197(4) 0.0254(4) -0.0025(3) -0.0003(3) 0.0027(4) O11 0.071(3) 0.044(2) 0.0359(18) -0.0026(16) -0.0165(17) -0.014(2) O12 0.0435(19) 0.0222(17) 0.052(2) -0.0011(14) -0.0113(16) -0.0037(14) O13 0.048(2) 0.0274(19) 0.053(2) 0.0086(14) -0.0069(16) 0.0092(14) O14 0.052(2) 0.053(3) 0.066(3) 0.008(2) 0.029(2) 0.0170(19) Cl2 0.0387(5) 0.0399(6) 0.0369(5) -0.0001(5) -0.0047(4) 0.0112(5) O21 0.055(2) 0.059(2) 0.0426(19) -0.0085(19) -0.0125(16) 0.027(2) O22 0.127(5) 0.069(3) 0.057(3) -0.014(2) 0.003(3) 0.036(3) O23 0.050(3) 0.215(11) 0.376(13) -0.218(11) -0.052(5) 0.020(5) O24 0.280(12) 0.091(6) 0.133(6) 0.062(5) 0.069(7) 0.067(7) Cl3 0.0261(5) 0.0603(8) 0.0293(5) 0.0030(5) 0.0006(4) 0.0033(5) O31 0.062(3) 0.182(7) 0.038(2) -0.009(3) -0.0085(18) 0.051(4) O32 0.061(3) 0.247(11) 0.123(5) 0.053(6) 0.050(3) 0.046(5) O33 0.175(8) 0.060(4) 0.187(8) -0.012(5) -0.014(6) -0.025(5) O34 0.069(3) 0.097(4) 0.053(2) -0.022(3) -0.026(2) 0.019(3) N21 0.042(2) 0.044(3) 0.040(2) -0.0030(18) -0.0098(17) -0.0003(18) C22 0.035(2) 0.041(3) 0.0246(18) -0.0022(18) -0.0002(16) -0.001(2) C23 0.035(3) 0.085(4) 0.041(3) 0.003(3) -0.011(2) 0.010(3) _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 O1 1.927(2) . ? Cu1 N1 2.051(3) . ? Cu1 N3C 2.089(3) . ? Cu1 N3A 2.107(3) . ? Cu1 N3B 2.197(3) . ? Cu2 O1 1.916(2) . ? Cu2 N2 2.047(3) . ? Cu2 N4C 2.103(3) . ? Cu2 N4A 2.144(3) . ? Cu2 N4B 2.261(3) . ? N1 C1C 1.487(5) . ? N1 C1A 1.489(5) . ? N1 C1B 1.492(5) . ? C1A C2A 1.519(6) . ? C2A N3A 1.478(5) . ? N3A C3A 1.501(5) . ? C3A C4A 1.520(6) . ? C4A C5A 1.515(6) . ? C5A N4A 1.494(5) . ? N4A C6A 1.483(5) . ? C6A C7A 1.509(6) . ? C7A N2 1.500(5) . ? N2 C7C 1.479(5) . ? N2 C7B 1.491(5) . ? C1B C2B 1.510(6) . ? C2B N3B 1.471(5) . ? N3B C3B 1.476(5) . ? C3B C4B 1.527(6) . ? C4B C5B 1.518(6) . ? C5B N4B 1.483(5) . ? N4B C6B 1.465(5) . ? C6B C7B 1.517(5) . ? C1C C2C 1.500(6) . ? C2C N3C 1.486(5) . ? N3C C3C 1.478(5) . ? C3C C4C 1.531(6) . ? C4C C5C 1.521(6) . ? C5C N4C 1.481(5) . ? N4C C6C 1.476(5) . ? C6C C7C 1.527(6) . ? Cl1 O11 1.413(3) . ? Cl1 O14 1.424(4) . ? Cl1 O13 1.433(3) . ? Cl1 O12 1.443(3) . ? Cl2 O23 1.324(6) . ? Cl2 O24 1.400(7) . ? Cl2 O21 1.414(4) . ? Cl2 O22 1.422(5) . ? Cl3 O32 1.362(5) . ? Cl3 O31 1.374(4) . ? Cl3 O34 1.406(4) . ? Cl3 O33 1.418(7) . ? N21 C22 1.116(6) . ? C22 C23 1.452(6) . ? 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 O1 Cu1 N1 175.85(14) . . ? O1 Cu1 N3C 94.76(12) . . ? N1 Cu1 N3C 84.43(13) . . ? O1 Cu1 N3A 91.44(11) . . ? N1 Cu1 N3A 85.74(12) . . ? N3C Cu1 N3A 125.34(14) . . ? O1 Cu1 N3B 101.60(12) . . ? N1 Cu1 N3B 82.25(13) . . ? N3C Cu1 N3B 121.48(13) . . ? N3A Cu1 N3B 110.10(13) . . ? O1 Cu2 N2 168.52(12) . . ? O1 Cu2 N4C 93.86(12) . . ? N2 Cu2 N4C 83.52(13) . . ? O1 Cu2 N4A 90.76(11) . . ? N2 Cu2 N4A 84.83(12) . . ? N4C Cu2 N4A 143.27(13) . . ? O1 Cu2 N4B 109.49(12) . . ? N2 Cu2 N4B 81.98(12) . . ? N4C Cu2 N4B 103.11(13) . . ? N4A Cu2 N4B 109.56(12) . . ? C1C N1 C1A 111.0(3) . . ? C1C N1 C1B 109.9(3) . . ? C1A N1 C1B 111.7(3) . . ? C1C N1 Cu1 108.1(2) . . ? C1A N1 Cu1 106.4(2) . . ? C1B N1 Cu1 109.7(2) . . ? N1 C1A C2A 110.3(3) . . ? N3A C2A C1A 107.8(3) . . ? C2A N3A C3A 114.2(3) . . ? C2A N3A Cu1 103.8(2) . . ? C3A N3A Cu1 117.2(2) . . ? N3A C3A C4A 112.5(3) . . ? C5A C4A C3A 115.3(3) . . ? N4A C5A C4A 114.6(3) . . ? C6A N4A C5A 108.9(3) . . ? C6A N4A Cu2 106.6(2) . . ? C5A N4A Cu2 128.4(2) . . ? N4A C6A C7A 109.6(3) . . ? N2 C7A C6A 110.0(3) . . ? C7C N2 C7B 109.8(3) . . ? C7C N2 C7A 110.4(3) . . ? C7B N2 C7A 111.4(3) . . ? C7C N2 Cu2 110.1(2) . . ? C7B N2 Cu2 110.4(2) . . ? C7A N2 Cu2 104.7(2) . . ? N1 C1B C2B 110.7(3) . . ? N3B C2B C1B 106.3(3) . . ? C2B N3B C3B 115.2(3) . . ? C2B N3B Cu1 101.5(2) . . ? C3B N3B Cu1 119.7(2) . . ? N3B C3B C4B 112.1(3) . . ? C5B C4B C3B 113.3(3) . . ? N4B C5B C4B 111.9(3) . . ? C6B N4B C5B 111.4(3) . . ? C6B N4B Cu2 104.7(2) . . ? C5B N4B Cu2 123.8(3) . . ? N4B C6B C7B 110.0(3) . . ? N2 C7B C6B 109.8(3) . . ? N1 C1C C2C 110.1(3) . . ? N3C C2C C1C 107.3(3) . . ? C3C N3C C2C 112.8(3) . . ? C3C N3C Cu1 117.6(3) . . ? C2C N3C Cu1 103.3(2) . . ? N3C C3C C4C 111.4(3) . . ? C5C C4C C3C 113.9(4) . . ? N4C C5C C4C 112.4(3) . . ? C6C N4C C5C 110.5(3) . . ? C6C N4C Cu2 103.7(2) . . ? C5C N4C Cu2 121.3(2) . . ? N4C C6C C7C 107.6(3) . . ? N2 C7C C6C 110.1(3) . . ? Cu2 O1 Cu1 155.60(17) . . ? O11 Cl1 O14 112.3(3) . . ? O11 Cl1 O13 109.5(2) . . ? O14 Cl1 O13 108.7(2) . . ? O11 Cl1 O12 109.7(2) . . ? O14 Cl1 O12 108.0(2) . . ? O13 Cl1 O12 108.4(2) . . ? O23 Cl2 O24 111.3(8) . . ? O23 Cl2 O21 113.7(4) . . ? O24 Cl2 O21 107.7(4) . . ? O23 Cl2 O22 110.5(6) . . ? O24 Cl2 O22 102.8(5) . . ? O21 Cl2 O22 110.3(3) . . ? O32 Cl3 O31 113.8(4) . . ? O32 Cl3 O34 112.7(5) . . ? O31 Cl3 O34 112.5(3) . . ? O32 Cl3 O33 109.4(6) . . ? O31 Cl3 O33 106.1(5) . . ? O34 Cl3 O33 101.2(5) . . ? N21 C22 C23 178.4(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3A H3A O14 0.93 2.48 3.121(5) 126.4 . N4A H4A O12 0.93 2.25 3.002(5) 136.9 . N4B H4B O13 0.93 2.18 3.020(4) 149.5 1_565 N3C H3C N21 0.93 2.21 3.118(5) 166.5 . O1 H1 O12 0.95 2.57 3.250(4) 128.7 . O1 H1 O14 0.95 2.32 3.203(6) 154.2 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.147 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.168