# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Alicia Beatty' _publ_contact_author_address ; Department of Chemistry Mississippi State University Box 9573 Mississippi State MS MS 39762 UNITED STATES OF AMERICA ; _publ_section_title ; From Crystal Engineering to Cluster Engineering: How to Transform Cadmium Chloride from 2-D to 0-D ; _publ_contact_author_email AB279@RA.MSSTATE.EDU loop_ _publ_author_name A.Beatty 'Chun-Long Chen' # Attachment 'ambcif11.CIF' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 612085' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 Cd2 Cl8 N4' _chemical_formula_weight 880.90 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' 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sn Sn -0.6537 1.4246 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.765(5) _cell_length_b 7.271(3) _cell_length_c 7.363(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.447(6) _cell_angle_gamma 90.00 _cell_volume 783.8(5) _cell_formula_units_Z 1 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used 3225 _cell_measurement_theta_min 2.783 _cell_measurement_theta_max 25.023 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.866 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 2.061 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6163 _exptl_absorpt_correction_T_max 0.9221 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5557 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1393 _reflns_number_gt 1255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material 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^)+(0.0240P)^2^+0.3877P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1393 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0228 _refine_ls_R_factor_gt 0.0187 _refine_ls_wR_factor_ref 0.0505 _refine_ls_wR_factor_gt 0.0473 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 Cd1 Cd 1.0000 0.0000 1.0000 0.02789(10) Uani 1 2 d S . . Cl1 Cl 0.82890(4) 0.05059(10) 0.97310(10) 0.04311(17) Uani 1 1 d . . . Cl2 Cl 1.02615(4) 0.20030(8) 1.30630(8) 0.03743(16) Uani 1 1 d . . . N1 N 0.82842(14) 0.0191(3) 1.4053(3) 0.0405(5) Uani 1 1 d . . . H1A H 0.8607 -0.0557 1.4847 0.061 Uiso 1 1 calc R . . H1B H 0.8471 0.1344 1.4265 0.061 Uiso 1 1 calc R . . H1C H 0.8365 -0.0127 1.2918 0.061 Uiso 1 1 calc R . . C1 C 0.73134(17) 0.0047(3) 1.4266(4) 0.0331(5) Uani 1 1 d . . . C2 C 0.66927(19) 0.1080(5) 1.3186(4) 0.0597(9) Uani 1 1 d . . . H2A H 0.6878 0.1808 1.2263 0.072 Uiso 1 1 calc R . . C3 C 0.57868(18) 0.1044(5) 1.3467(4) 0.0577(9) Uani 1 1 d . . . H3A H 0.5366 0.1748 1.2717 0.069 Uiso 1 1 calc R . . C4 C 0.54875(17) -0.0009(3) 1.4830(3) 0.0313(5) Uani 1 1 d . . . C5 C 0.61385(18) -0.1060(4) 1.5874(4) 0.0525(8) Uani 1 1 d . . . H5A H 0.5960 -0.1807 1.6790 0.063 Uiso 1 1 calc R . . C6 C 0.70461(17) -0.1034(4) 1.5599(4) 0.0484(7) Uani 1 1 d . . . H6A H 0.7471 -0.1754 1.6323 0.058 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 Cd1 0.02700(15) 0.02871(15) 0.02891(15) 0.00028(9) 0.00717(10) 0.00027(9) Cl1 0.0276(3) 0.0508(4) 0.0512(4) 0.0024(3) 0.0062(3) 0.0021(3) Cl2 0.0433(3) 0.0348(3) 0.0346(3) -0.0093(2) 0.0064(3) 0.0022(3) N1 0.0265(11) 0.0463(13) 0.0498(14) 0.0016(10) 0.0094(10) -0.0012(9) C1 0.0256(12) 0.0371(14) 0.0379(14) -0.0042(10) 0.0089(10) -0.0015(9) C2 0.0354(15) 0.080(2) 0.066(2) 0.0390(17) 0.0170(14) 0.0047(15) C3 0.0289(14) 0.078(2) 0.067(2) 0.0413(17) 0.0097(13) 0.0100(14) C4 0.0277(13) 0.0321(13) 0.0347(13) -0.0021(10) 0.0066(10) -0.0020(9) C5 0.0356(14) 0.067(2) 0.0579(18) 0.0309(16) 0.0181(13) 0.0084(13) C6 0.0315(13) 0.0606(19) 0.0540(17) 0.0217(14) 0.0095(12) 0.0119(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 Cl1 2.5352(10) 3_757 ? Cd1 Cl1 2.5352(11) . ? Cd1 Cl2 2.6597(9) 2_747 ? Cd1 Cl2 2.6598(9) 4_565 ? Cd1 Cl2 2.6704(9) 3_757 ? Cd1 Cl2 2.6704(9) . ? Cl2 Cd1 2.6598(9) 2_757 ? N1 C1 1.466(3) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C1 C6 1.355(4) . ? C1 C2 1.359(4) . ? C2 C3 1.380(4) . ? C2 H2A 0.9300 . ? C3 C4 1.380(4) . ? C3 H3A 0.9300 . ? C4 C5 1.381(4) . ? C4 C4 1.493(5) 3_658 ? C5 C6 1.381(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? 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 Cl1 Cd1 Cl1 180.0 3_757 . ? Cl1 Cd1 Cl2 92.96(2) 3_757 2_747 ? Cl1 Cd1 Cl2 87.04(2) . 2_747 ? Cl1 Cd1 Cl2 87.04(2) 3_757 4_565 ? Cl1 Cd1 Cl2 92.96(2) . 4_565 ? Cl2 Cd1 Cl2 180.0 2_747 4_565 ? Cl1 Cd1 Cl2 91.17(2) 3_757 3_757 ? Cl1 Cd1 Cl2 88.83(2) . 3_757 ? Cl2 Cd1 Cl2 89.48(3) 2_747 3_757 ? Cl2 Cd1 Cl2 90.52(3) 4_565 3_757 ? Cl1 Cd1 Cl2 88.83(2) 3_757 . ? Cl1 Cd1 Cl2 91.17(2) . . ? Cl2 Cd1 Cl2 90.52(3) 2_747 . ? Cl2 Cd1 Cl2 89.48(3) 4_565 . ? Cl2 Cd1 Cl2 180.0 3_757 . ? Cd1 Cl2 Cd1 152.20(3) 2_757 . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C6 C1 C2 120.4(2) . . ? C6 C1 N1 120.0(2) . . ? C2 C1 N1 119.5(2) . . ? C1 C2 C3 119.6(3) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C4 C3 C2 121.9(2) . . ? C4 C3 H3A 119.1 . . ? C2 C3 H3A 119.1 . . ? C3 C4 C5 116.5(2) . . ? C3 C4 C4 121.6(3) . 3_658 ? C5 C4 C4 121.9(3) . 3_658 ? C4 C5 C6 121.9(2) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C1 C6 C5 119.6(2) . . ? C1 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? 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 N1 H1A Cl2 0.89 2.37 3.238(2) 166.2 3_758 N1 H1B Cl1 0.89 2.34 3.168(2) 155.6 4_566 N1 H1B Cl2 0.89 2.93 3.368(2) 111.8 . N1 H1C Cl1 0.89 2.38 3.192(3) 151.8 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.288 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.062 #####END data_complex2 _database_code_depnum_ccdc_archive 'CCDC 612086' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cd Cl4 N2' _chemical_formula_weight 466.49 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' Cl Cl 0.1484 0.1585 '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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.079(3) _cell_length_b 7.3585(15) _cell_length_c 7.2742(14) _cell_angle_alpha 90.00 _cell_angle_beta 97.423(3) _cell_angle_gamma 90.00 _cell_volume 906.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2286 _cell_measurement_theta_min 3.609 _cell_measurement_theta_max 24.854 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 1.788 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7163 _exptl_absorpt_correction_T_max 0.9319 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6414 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1609 _reflns_number_gt 1339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material 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^)+(0.0625P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1609 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.195 _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 0.5000 0.0000 0.0000 0.02713(19) Uani 1 2 d S . . Cl1 Cl 0.35177(7) 0.05057(18) -0.02820(18) 0.0410(3) Uani 1 1 d . . . Cl2 Cl 0.52212(7) 0.29778(16) -0.19450(15) 0.0374(3) Uani 1 1 d . . . N1 N 0.6482(3) 0.5271(5) 0.0886(7) 0.0433(11) Uani 1 1 d . . . H1A H 0.6191 0.4511 0.0128 0.065 Uiso 1 1 calc R . . H1B H 0.6336 0.6410 0.0607 0.065 Uiso 1 1 calc R . . H1C H 0.6411 0.5033 0.2052 0.065 Uiso 1 1 calc R . . C1 C 0.7314(3) 0.5039(6) 0.0673(7) 0.0360(11) Uani 1 1 d . . . C2 C 0.7526(3) 0.3828(7) -0.0595(7) 0.0461(13) Uani 1 1 d . . . H2B H 0.7144 0.3106 -0.1269 0.055 Uiso 1 1 calc R . . C3 C 0.8303(3) 0.3676(9) -0.0876(8) 0.0569(15) Uani 1 1 d . . . H3A H 0.8442 0.2854 -0.1749 0.068 Uiso 1 1 calc R . . C4 C 0.8877(4) 0.4720(8) 0.0111(10) 0.0557(16) Uani 1 1 d . . . C5 C 0.8646(3) 0.5944(9) 0.1430(8) 0.0587(15) Uani 1 1 d . . . H5A H 0.9025 0.6665 0.2116 0.070 Uiso 1 1 calc R . . C6 C 0.7865(3) 0.6087(8) 0.1715(7) 0.0498(13) Uani 1 1 d . . . H6A H 0.7715 0.6883 0.2600 0.060 Uiso 1 1 calc R . . C7 C 0.9704(4) 0.4540(11) -0.0316(11) 0.0705(19) Uani 1 1 d . . . H7A H 0.9792 0.3633 -0.1156 0.085 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 Cd1 0.0273(3) 0.0274(3) 0.0275(3) -0.00040(17) 0.00668(19) 0.00049(17) Cl1 0.0293(6) 0.0443(7) 0.0491(7) 0.0010(5) 0.0046(5) 0.0025(5) Cl2 0.0427(7) 0.0352(6) 0.0345(6) 0.0102(5) 0.0060(5) -0.0019(5) N1 0.029(2) 0.041(2) 0.061(3) 0.0031(19) 0.009(2) 0.0041(17) C1 0.027(2) 0.041(3) 0.041(3) 0.008(2) 0.009(2) 0.002(2) C2 0.037(3) 0.050(3) 0.052(3) -0.008(3) 0.010(2) 0.000(2) C3 0.046(3) 0.064(4) 0.065(4) -0.012(3) 0.024(3) -0.001(3) C4 0.042(3) 0.057(4) 0.071(4) 0.009(3) 0.018(3) 0.009(3) C5 0.035(3) 0.061(4) 0.079(4) -0.008(3) 0.003(3) -0.008(3) C6 0.035(3) 0.058(4) 0.057(3) -0.013(3) 0.007(2) 0.000(3) C7 0.050(4) 0.074(5) 0.091(5) -0.011(4) 0.022(4) -0.005(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 Cd1 Cl1 2.5408(13) 3_655 ? Cd1 Cl1 2.5408(13) . ? Cd1 Cl2 2.6605(11) 4_566 ? Cd1 Cl2 2.6605(11) 2_644 ? Cd1 Cl2 2.6616(11) . ? Cd1 Cl2 2.6616(11) 3_655 ? Cl2 Cd1 2.6605(11) 2_654 ? N1 C1 1.459(7) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C1 C2 1.364(7) . ? C1 C6 1.367(7) . ? C2 C3 1.372(7) . ? C2 H2B 0.9300 . ? C3 C4 1.374(9) . ? C3 H3A 0.9300 . ? C4 C5 1.409(9) . ? C4 C7 1.491(10) . ? C5 C6 1.381(7) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C7 1.253(14) 3_765 ? C7 H7A 0.9300 . ? 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 Cl1 Cd1 Cl1 180.00(6) 3_655 . ? Cl1 Cd1 Cl2 88.97(4) 3_655 4_566 ? Cl1 Cd1 Cl2 91.03(4) . 4_566 ? Cl1 Cd1 Cl2 91.03(4) 3_655 2_644 ? Cl1 Cd1 Cl2 88.97(4) . 2_644 ? Cl2 Cd1 Cl2 180.00(5) 4_566 2_644 ? Cl1 Cd1 Cl2 87.43(4) 3_655 . ? Cl1 Cd1 Cl2 92.57(4) . . ? Cl2 Cd1 Cl2 88.221(18) 4_566 . ? Cl2 Cd1 Cl2 91.779(18) 2_644 . ? Cl1 Cd1 Cl2 92.57(4) 3_655 3_655 ? Cl1 Cd1 Cl2 87.43(4) . 3_655 ? Cl2 Cd1 Cl2 91.779(18) 4_566 3_655 ? Cl2 Cd1 Cl2 88.221(18) 2_644 3_655 ? Cl2 Cd1 Cl2 180.00(6) . 3_655 ? Cd1 Cl2 Cd1 152.86(5) 2_654 . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C2 C1 C6 121.3(5) . . ? C2 C1 N1 119.7(5) . . ? C6 C1 N1 119.0(4) . . ? C1 C2 C3 120.0(5) . . ? C1 C2 H2B 120.0 . . ? C3 C2 H2B 120.0 . . ? C2 C3 C4 121.0(5) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C3 C4 C5 118.0(5) . . ? C3 C4 C7 118.2(6) . . ? C5 C4 C7 123.7(6) . . ? C6 C5 C4 120.8(5) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C1 C6 C5 118.8(5) . . ? C1 C6 H6A 120.6 . . ? C5 C6 H6A 120.6 . . ? C7 C7 C4 128.0(10) 3_765 . ? C7 C7 H7A 116.0 3_765 . ? C4 C7 H7A 116.0 . . ? 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 N1 H1A Cl2 0.89 2.38 3.252(5) 168.1 . N1 H1B Cl1 0.89 2.30 3.139(4) 157.3 3_665 N1 H1C Cl1 0.89 2.36 3.203(5) 157.4 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.942 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.245 #####END data_complex3 _database_code_depnum_ccdc_archive 'CCDC 612087' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C112 H144 Cd4 Cl24 N16' _chemical_formula_weight 3014.83 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' Cl Cl 0.1484 0.1585 '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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 8.094(2) _cell_length_b 48.185(11) _cell_length_c 8.239(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3213.1(13) _cell_formula_units_Z 1 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used 2922 _cell_measurement_theta_min 2.779 _cell_measurement_theta_max 21.353 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 1.204 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7861 _exptl_absorpt_correction_T_max 0.9648 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22004 _diffrn_reflns_av_R_equivalents 0.0775 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -57 _diffrn_reflns_limit_k_max 57 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 0.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2862 _reflns_number_gt 2089 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material 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^)+(0.0661P)^2^+1.2030P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2862 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _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 0.07953(8) 0.2500 0.45004(7) 0.0377(2) Uani 1 2 d S . . Cl1 Cl -0.0555(3) 0.2500 0.1803(2) 0.0470(5) Uani 1 2 d S . . Cl2 Cl 0.16185(17) 0.29789(3) 0.51983(16) 0.0372(3) Uani 1 1 d . . . Cl3 Cl -0.1626(2) 0.2500 0.6543(3) 0.0421(5) Uani 1 2 d S . . Cl4 Cl -0.01236(19) 0.48733(3) 0.73096(18) 0.0454(4) Uani 1 1 d . . . N1 N 0.0471(5) 0.29544(8) 0.8971(5) 0.0331(11) Uani 1 1 d . . . H1A H 0.0939 0.2814 0.9504 0.050 Uiso 1 1 calc R . . H1B H 0.0804 0.2952 0.7942 0.050 Uiso 1 1 calc R . . H1C H -0.0623 0.2937 0.9010 0.050 Uiso 1 1 calc R . . N2 N 0.2788(6) 0.47468(8) 1.4525(5) 0.0399(11) Uani 1 1 d . . . H2A H 0.2986 0.4876 1.3779 0.060 Uiso 1 1 calc R . . H2B H 0.3624 0.4741 1.5227 0.060 Uiso 1 1 calc R . . H2C H 0.1858 0.4787 1.5050 0.060 Uiso 1 1 calc R . . C1 C 0.0958(6) 0.32189(10) 0.9731(6) 0.0290(11) Uani 1 1 d . . . C2 C 0.0362(6) 0.34679(10) 0.9084(6) 0.0293(12) Uani 1 1 d . . . C3 C 0.0820(6) 0.37100(10) 0.9895(6) 0.0307(11) Uani 1 1 d . . . H3A H 0.0453 0.3879 0.9491 0.037 Uiso 1 1 calc R . . C4 C 0.1794(6) 0.37099(10) 1.1272(6) 0.0295(11) Uani 1 1 d . . . C5 C 0.2383(7) 0.34561(10) 1.1849(6) 0.0403(14) Uani 1 1 d . . . H5A H 0.3062 0.3452 1.2759 0.048 Uiso 1 1 calc R . . C6 C 0.1969(7) 0.32103(10) 1.1084(6) 0.0343(12) Uani 1 1 d . . . H6A H 0.2364 0.3042 1.1473 0.041 Uiso 1 1 calc R . . C7 C 0.2151(6) 0.39747(10) 1.2121(6) 0.0345(12) Uani 1 1 d . . . C8 C 0.2075(6) 0.39939(11) 1.3814(6) 0.0347(12) Uani 1 1 d . . . H8A H 0.1857 0.3834 1.4406 0.042 Uiso 1 1 calc R . . C9 C 0.2307(7) 0.42391(10) 1.4649(6) 0.0350(12) Uani 1 1 d . . . C10 C 0.2618(6) 0.44724(10) 1.3725(6) 0.0343(12) Uani 1 1 d . . . C11 C 0.2741(7) 0.44661(11) 1.2057(7) 0.0444(15) Uani 1 1 d . . . H11A H 0.2980 0.4627 1.1481 0.053 Uiso 1 1 calc R . . C12 C 0.2505(7) 0.42176(11) 1.1249(7) 0.0448(15) Uani 1 1 d . . . H12A H 0.2581 0.4211 1.0124 0.054 Uiso 1 1 calc R . . C13 C -0.0735(8) 0.34825(12) 0.7626(7) 0.0468(15) Uani 1 1 d . . . H13A H -0.0997 0.3673 0.7397 0.070 Uiso 1 1 calc R . . H13B H -0.1736 0.3382 0.7834 0.070 Uiso 1 1 calc R . . H13C H -0.0177 0.3402 0.6710 0.070 Uiso 1 1 calc R . . C14 C 0.2198(9) 0.42445(12) 1.6473(7) 0.0535(17) Uani 1 1 d . . . H14A H 0.1973 0.4061 1.6868 0.080 Uiso 1 1 calc R . . H14B H 0.1325 0.4367 1.6800 0.080 Uiso 1 1 calc R . . H14C H 0.3227 0.4309 1.6915 0.080 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 Cd1 0.0529(4) 0.0287(3) 0.0316(3) 0.000 -0.0067(3) 0.000 Cl1 0.0581(13) 0.0504(12) 0.0325(10) 0.000 -0.0118(10) 0.000 Cl2 0.0454(8) 0.0305(7) 0.0356(7) -0.0025(5) 0.0003(6) -0.0036(6) Cl3 0.0401(11) 0.0364(11) 0.0498(12) 0.000 0.0016(10) 0.000 Cl4 0.0477(9) 0.0443(8) 0.0441(8) 0.0038(7) 0.0074(7) -0.0023(7) N1 0.042(3) 0.025(2) 0.032(2) -0.0056(18) 0.002(2) -0.0036(19) N2 0.050(3) 0.025(2) 0.044(3) -0.008(2) -0.011(2) 0.001(2) C1 0.033(3) 0.022(2) 0.031(3) -0.003(2) 0.006(2) -0.003(2) C2 0.027(3) 0.032(3) 0.029(3) -0.003(2) 0.002(2) 0.001(2) C3 0.034(3) 0.026(3) 0.032(3) 0.000(2) 0.000(2) 0.002(2) C4 0.038(3) 0.023(3) 0.028(3) -0.005(2) 0.004(2) -0.004(2) C5 0.058(4) 0.032(3) 0.032(3) -0.001(2) -0.014(3) -0.001(3) C6 0.046(3) 0.025(3) 0.033(3) 0.003(2) -0.005(3) 0.003(2) C7 0.040(3) 0.030(3) 0.033(3) -0.005(2) -0.001(2) -0.002(2) C8 0.041(3) 0.028(3) 0.035(3) 0.000(2) -0.004(2) -0.005(2) C9 0.038(3) 0.032(3) 0.034(3) -0.004(2) -0.005(3) 0.001(2) C10 0.041(3) 0.026(3) 0.036(3) -0.007(2) -0.004(3) -0.003(2) C11 0.067(4) 0.025(3) 0.041(3) 0.003(2) -0.006(3) -0.011(3) C12 0.064(4) 0.040(3) 0.031(3) -0.006(3) 0.002(3) -0.013(3) C13 0.053(4) 0.041(3) 0.046(4) -0.004(3) -0.016(3) 0.002(3) C14 0.091(5) 0.036(3) 0.034(3) -0.001(3) 0.002(3) -0.002(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 Cd1 Cl2 2.4697(14) 7_565 ? Cd1 Cl2 2.4697(14) . ? Cd1 Cl1 2.477(2) . ? Cd1 Cl3 2.583(2) . ? N1 C1 1.473(6) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 C10 1.484(6) . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? C1 C6 1.383(7) . ? C1 C2 1.399(7) . ? C2 C3 1.395(7) . ? C2 C13 1.496(7) . ? C3 C4 1.381(7) . ? C3 H3A 0.9300 . ? C4 C5 1.396(7) . ? C4 C7 1.483(7) . ? C5 C6 1.383(7) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.400(7) . ? C7 C12 1.403(7) . ? C8 C9 1.380(7) . ? C8 H8A 0.9300 . ? C9 C10 1.381(7) . ? C9 C14 1.506(7) . ? C10 C11 1.378(7) . ? C11 C12 1.383(7) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 Cl2 Cd1 Cl2 138.25(7) 7_565 . ? Cl2 Cd1 Cl1 109.15(4) 7_565 . ? Cl2 Cd1 Cl1 109.15(3) . . ? Cl2 Cd1 Cl3 93.04(4) 7_565 . ? Cl2 Cd1 Cl3 93.04(4) . . ? Cl1 Cd1 Cl3 104.46(7) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C10 N2 H2A 109.5 . . ? C10 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C10 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C6 C1 C2 122.5(4) . . ? C6 C1 N1 118.3(4) . . ? C2 C1 N1 119.2(4) . . ? C3 C2 C1 116.3(4) . . ? C3 C2 C13 120.2(5) . . ? C1 C2 C13 123.4(5) . . ? C4 C3 C2 123.0(5) . . ? C4 C3 H3A 118.5 . . ? C2 C3 H3A 118.5 . . ? C3 C4 C5 118.4(4) . . ? C3 C4 C7 119.8(4) . . ? C5 C4 C7 121.8(5) . . ? C6 C5 C4 120.8(5) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C5 C6 C1 119.0(5) . . ? C5 C6 H6A 120.5 . . ? C1 C6 H6A 120.5 . . ? C8 C7 C12 117.7(5) . . ? C8 C7 C4 121.2(5) . . ? C12 C7 C4 121.1(5) . . ? C9 C8 C7 123.2(5) . . ? C9 C8 H8A 118.4 . . ? C7 C8 H8A 118.4 . . ? C8 C9 C10 116.5(5) . . ? C8 C9 C14 120.3(5) . . ? C10 C9 C14 123.2(5) . . ? C11 C10 C9 123.0(5) . . ? C11 C10 N2 117.1(5) . . ? C9 C10 N2 119.8(5) . . ? C10 C11 C12 119.3(5) . . ? C10 C11 H11A 120.4 . . ? C12 C11 H11A 120.4 . . ? C11 C12 C7 120.3(5) . . ? C11 C12 H12A 119.9 . . ? C7 C12 H12A 119.9 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 H2A Cl4 0.89 2.43 3.202(5) 145.0 2_565 N2 H2A Cl4 0.89 2.76 3.208(5) 112.3 5_567 N2 H2B Cl4 0.89 2.36 3.167(5) 151.5 6_658 N2 H2C Cl4 0.89 2.49 3.345(5) 160.7 1_556 N1 H1A Cl3 0.89 2.63 3.239(4) 126.4 6_657 N1 H1A Cl1 0.89 2.71 3.306(5) 125.4 1_556 N1 H1B Cl2 0.89 2.36 3.247(5) 176.1 . N1 H1C Cl2 0.89 2.34 3.195(4) 162.4 6_557 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.605 _refine_diff_density_min -1.272 _refine_diff_density_rms 0.216 #####END data_complex4 _database_code_depnum_ccdc_archive 'CCDC 612088' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C128 H224 Cd12 Cl40 N16 O24' _chemical_formula_weight 5138.03 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4/mnc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' 'y+1/2, x+1/2, -z+1/2' '-y+1/2, -x+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z' 'y, -x, -z' '-y, x, -z' 'x-1/2, -y-1/2, z-1/2' '-x-1/2, y-1/2, z-1/2' '-y-1/2, -x-1/2, z-1/2' 'y-1/2, x-1/2, z-1/2' _cell_length_a 12.546(3) _cell_length_b 12.546(3) _cell_length_c 32.740(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5154(2) _cell_formula_units_Z 1 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 3901 _cell_measurement_theta_min 2.611 _cell_measurement_theta_max 24.940 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2552 _exptl_absorpt_coefficient_mu 1.785 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7166 _exptl_absorpt_correction_T_max 0.8011 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 301(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23117 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2328 _reflns_number_gt 1763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material 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^)+(0.0219P)^2^+14.7148P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2328 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0769 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.064 _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 Cd1 Cd 0.09605(4) 0.20692(4) 0.0000 0.03265(14) Uani 1 2 d S . . Cd2 Cd 0.0000 0.0000 -0.09295(2) 0.03617(18) Uani 1 4 d S . . Cl1 Cl 0.17404(14) 0.39445(13) 0.0000 0.0461(4) Uani 1 2 d S . . Cl2 Cl 0.27448(12) 0.10101(12) 0.0000 0.0334(3) Uani 1 2 d S . . Cl3 Cl 0.0000 0.0000 0.0000 0.0314(7) Uani 1 8 d S . . Cl4 Cl 0.08808(9) 0.18776(9) -0.07923(3) 0.0348(3) Uani 1 1 d . . . Cl5 Cl 0.0000 0.0000 -0.16759(7) 0.0452(6) Uani 1 4 d S . . Cl6 Cl 0.5000 0.5000 0.0000 0.129(3) Uani 1 8 d S . . O1W O 0.5000 0.0000 0.05762(13) 0.0474(12) Uani 1 2 d S . . H1WA H 0.5304 0.0444 0.0366 0.057 Uiso 0.50 1 d PR . . H1WB H 0.5000 0.0000 0.0862 0.057 Uiso 1 2 d SR . . O2W O 0.3755(4) 0.3253(4) -0.06019(16) 0.1007(17) Uani 1 1 d . . . H2WA H 0.4188 0.2849 -0.0507 0.121 Uiso 1 1 d R . . H2WB H 0.4248 0.3841 -0.0480 0.121 Uiso 1 1 d R . . N1 N 0.3484(3) 0.1282(3) -0.09849(11) 0.0452(10) Uani 1 1 d . . . H1A H 0.2845 0.1035 -0.0915 0.068 Uiso 1 1 calc R . . H1B H 0.3552 0.1952 -0.0899 0.068 Uiso 1 1 calc R . . H1C H 0.3987 0.0881 -0.0870 0.068 Uiso 1 1 calc R . . C1 C 0.3598(4) 0.1246(4) -0.14330(14) 0.0431(12) Uani 1 1 d . . . C2 C 0.4532(4) 0.1588(4) -0.16152(16) 0.0477(13) Uani 1 1 d . . . C3 C 0.4561(4) 0.1569(5) -0.20371(16) 0.0578(15) Uani 1 1 d . . . H3A H 0.5178 0.1802 -0.2167 0.069 Uiso 1 1 calc R . . C4 C 0.3723(5) 0.1222(4) -0.22758(15) 0.0551(14) Uani 1 1 d . . . C5 C 0.2819(5) 0.0849(5) -0.20763(17) 0.0652(17) Uani 1 1 d . . . H5A H 0.2249 0.0587 -0.2228 0.078 Uiso 1 1 calc R . . C6 C 0.2759(4) 0.0864(5) -0.16569(16) 0.0555(15) Uani 1 1 d . . . H6A H 0.2151 0.0614 -0.1526 0.067 Uiso 1 1 calc R . . C7 C 0.5473(5) 0.1983(6) -0.13742(18) 0.078(2) Uani 1 1 d . . . H7A H 0.5671 0.1442 -0.1181 0.093 Uiso 1 1 d R . . H7B H 0.5249 0.2598 -0.1222 0.093 Uiso 1 1 d R . . C8 C 0.6378(9) 0.2279(14) -0.1594(4) 0.112(6) Uani 0.60 1 d P . . H8A H 0.6778 0.1647 -0.1656 0.168 Uiso 0.60 1 d PR . . H8B H 0.6158 0.2615 -0.1844 0.168 Uiso 0.60 1 d PR . . H8C H 0.6815 0.2762 -0.1440 0.168 Uiso 0.60 1 d PR . . C8' C 0.571(2) 0.3237(19) -0.1495(8) 0.134(10) Uani 0.40 1 d P . . H8'A H 0.6306 0.3491 -0.1337 0.201 Uiso 0.40 1 d PR . . H8'B H 0.5893 0.3259 -0.1780 0.201 Uiso 0.40 1 d PR . . H8'C H 0.5104 0.3682 -0.1446 0.201 Uiso 0.40 1 d PR . . 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 0.0341(3) 0.0323(3) 0.0316(3) 0.000 0.000 0.0010(2) Cd2 0.0358(2) 0.0358(2) 0.0370(4) 0.000 0.000 0.000 Cl1 0.0423(9) 0.0337(9) 0.0623(12) 0.000 0.000 -0.0057(8) Cl2 0.0316(8) 0.0329(8) 0.0358(9) 0.000 0.000 -0.0008(6) Cl3 0.0288(9) 0.0288(9) 0.0365(17) 0.000 0.000 0.000 Cl4 0.0381(6) 0.0359(6) 0.0303(6) 0.0012(5) -0.0003(5) -0.0012(5) Cl5 0.0498(9) 0.0498(9) 0.0359(13) 0.000 0.000 0.000 Cl6 0.077(2) 0.077(2) 0.233(9) 0.000 0.000 0.000 O1W 0.053(3) 0.063(3) 0.027(2) 0.000 0.000 0.004(3) O2W 0.114(4) 0.085(3) 0.103(4) -0.019(3) 0.021(3) -0.011(3) N1 0.045(2) 0.058(3) 0.032(2) 0.006(2) 0.0012(19) 0.000(2) C1 0.051(3) 0.049(3) 0.029(3) 0.006(2) 0.004(2) -0.003(2) C2 0.042(3) 0.063(4) 0.038(3) 0.005(3) 0.001(2) -0.005(2) C3 0.051(3) 0.076(4) 0.046(3) 0.009(3) 0.009(3) -0.016(3) C4 0.065(4) 0.060(4) 0.040(3) 0.003(3) 0.006(3) -0.021(3) C5 0.065(4) 0.090(5) 0.041(3) 0.006(3) -0.004(3) -0.033(3) C6 0.050(3) 0.081(4) 0.036(3) 0.003(3) 0.004(2) -0.028(3) C7 0.052(4) 0.132(6) 0.049(4) 0.009(4) -0.003(3) -0.022(4) C8 0.065(8) 0.192(17) 0.079(9) 0.030(11) -0.020(7) -0.060(10) C8' 0.14(2) 0.14(2) 0.12(2) 0.008(17) -0.045(18) -0.083(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 Cl1 2.5483(18) . ? Cd1 Cl2 2.6033(16) . ? Cd1 Cl4 2.6069(13) 10 ? Cd1 Cl4 2.6069(13) . ? Cd1 Cl2 2.6136(17) 3 ? Cd1 Cl3 2.8621(8) . ? Cd2 Cl5 2.444(3) . ? Cd2 Cl4 2.6405(12) . ? Cd2 Cl4 2.6405(12) 2 ? Cd2 Cl4 2.6405(12) 4 ? Cd2 Cl4 2.6405(12) 3 ? Cl2 Cd1 2.6136(17) 11 ? Cl3 Cd1 2.8621(7) 9 ? Cl3 Cd1 2.8621(7) 3 ? Cl3 Cd1 2.8621(8) 11 ? O1W H1WA 0.9640 . ? O1W H1WB 0.9364 . ? O2W H2WA 0.8043 . ? O2W H2WB 1.0415 . ? N1 C1 1.475(6) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C1 C6 1.369(7) . ? C1 C2 1.383(7) . ? C2 C3 1.382(7) . ? C2 C7 1.504(7) . ? C3 C4 1.381(7) . ? C3 H3A 0.9300 . ? C4 C5 1.389(7) . ? C4 C4 1.471(10) 8_554 ? C5 C6 1.375(7) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.394(12) . ? C7 C8' 1.65(2) . ? C7 H7A 0.9599 . ? C7 H7B 0.9600 . ? C8 C8' 1.50(3) . ? C8 H8A 0.9599 . ? C8 H8B 0.9601 . ? C8 H8C 0.9601 . ? C8 H8'B 1.5014 . ? C8' H7B 1.3352 . ? C8' H8B 1.4910 . ? C8' H8C 1.5157 . ? C8' H8'A 0.9599 . ? C8' H8'B 0.9602 . ? C8' H8'C 0.9599 . ? 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 Cl1 Cd1 Cl2 98.11(5) . . ? Cl1 Cd1 Cl4 95.73(3) . 10 ? Cl2 Cd1 Cl4 89.19(3) . 10 ? Cl1 Cd1 Cl4 95.73(3) . . ? Cl2 Cd1 Cl4 89.19(3) . . ? Cl4 Cd1 Cl4 168.54(5) 10 . ? Cl1 Cd1 Cl2 93.66(5) . 3 ? Cl2 Cd1 Cl2 168.23(5) . 3 ? Cl4 Cd1 Cl2 89.63(3) 10 3 ? Cl4 Cd1 Cl2 89.63(3) . 3 ? Cl1 Cd1 Cl3 177.68(4) . . ? Cl2 Cd1 Cl3 84.21(4) . . ? Cl4 Cd1 Cl3 84.27(3) 10 . ? Cl4 Cd1 Cl3 84.27(3) . . ? Cl2 Cd1 Cl3 84.02(3) 3 . ? Cl5 Cd2 Cl4 99.80(3) . . ? Cl5 Cd2 Cl4 99.80(3) . 2 ? Cl4 Cd2 Cl4 160.41(5) . 2 ? Cl5 Cd2 Cl4 99.80(3) . 4 ? Cl4 Cd2 Cl4 88.341(9) . 4 ? Cl4 Cd2 Cl4 88.341(9) 2 4 ? Cl5 Cd2 Cl4 99.80(3) . 3 ? Cl4 Cd2 Cl4 88.341(9) . 3 ? Cl4 Cd2 Cl4 88.341(9) 2 3 ? Cl4 Cd2 Cl4 160.41(5) 4 3 ? Cd1 Cl2 Cd1 101.77(5) . 11 ? Cd1 Cl3 Cd1 180.000(8) 9 . ? Cd1 Cl3 Cd1 90.0 9 3 ? Cd1 Cl3 Cd1 90.0 . 3 ? Cd1 Cl3 Cd1 90.0 9 11 ? Cd1 Cl3 Cd1 90.0 . 11 ? Cd1 Cl3 Cd1 180.000(8) 3 11 ? Cd1 Cl4 Cd2 105.52(4) . . ? H1WA O1W H1WB 135.6 . . ? H2WA O2W H2WB 84.2 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C6 C1 C2 121.9(5) . . ? C6 C1 N1 118.0(4) . . ? C2 C1 N1 120.1(5) . . ? C3 C2 C1 116.6(5) . . ? C3 C2 C7 120.6(5) . . ? C1 C2 C7 122.8(5) . . ? C4 C3 C2 123.4(5) . . ? C4 C3 H3A 118.3 . . ? C2 C3 H3A 118.3 . . ? C3 C4 C5 117.5(5) . . ? C3 C4 C4 120.9(6) . 8_554 ? C5 C4 C4 121.6(6) . 8_554 ? C6 C5 C4 120.6(5) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C1 C6 C5 119.8(5) . . ? C1 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? C8 C7 C2 117.1(7) . . ? C8 C7 C8' 58.2(10) . . ? C2 C7 C8' 109.3(9) . . ? C8 C7 H7A 108.6 . . ? C2 C7 H7A 108.4 . . ? C8' C7 H7A 141.7 . . ? C8 C7 H7B 107.0 . . ? C2 C7 H7B 107.8 . . ? C8' C7 H7B 54.0 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C8' 69.5(11) . . ? C7 C8 H8A 108.3 . . ? C8' C8 H8A 177.6 . . ? C7 C8 H8B 108.8 . . ? C8' C8 H8B 70.9 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 111.2 . . ? C8' C8 H8C 72.4 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C8 H8'B 95.6 . . ? C8' C8 H8'B 37.3 . . ? H8A C8 H8'B 143.4 . . ? H8B C8 H8'B 34.8 . . ? H8C C8 H8'B 85.8 . . ? C8 C8' C7 52.3(9) . . ? C8 C8' H7B 84.6 . . ? C7 C8' H7B 35.6 . . ? C8 C8' H8B 37.5 . . ? C7 C8' H8B 75.7 . . ? H7B C8' H8B 111.2 . . ? C8 C8' H8C 37.1 . . ? C7 C8' H8C 76.3 . . ? H7B C8' H8C 94.7 . . ? H8B C8' H8C 62.9 . . ? C8 C8' H8'A 87.2 . . ? C7 C8' H8'A 109.1 . . ? H7B C8' H8'A 100.1 . . ? H8B C8' H8'A 107.2 . . ? H8C C8' H8'A 50.2 . . ? C8 C8' H8'B 71.5 . . ? C7 C8' H8'B 107.7 . . ? H7B C8' H8'B 140.4 . . ? H8B C8' H8'B 35.3 . . ? H8C C8' H8'B 85.0 . . ? H8'A C8' H8'B 109.5 . . ? C8 C8' H8'C 161.0 . . ? C7 C8' H8'C 111.6 . . ? H7B C8' H8'C 83.7 . . ? H8B C8' H8'C 137.0 . . ? H8C C8' H8'C 159.2 . . ? H8'A C8' H8'C 109.5 . . ? H8'B C8' H8'C 109.5 . . ? 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 O1W H1WA Cl1 0.96 2.23 3.175(3) 166.5 3_655 O2W H2WB Cl6 1.04 2.34 3.336(5) 159.4 . N1 H1A Cl4 0.89 2.71 3.409(4) 136.2 . N1 H1A Cl4 0.89 2.72 3.439(4) 138.3 4 N1 H1B O2W 0.89 1.92 2.793(6) 167.5 . N1 H1C O1W 0.89 1.94 2.828(4) 174.7 9_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.558 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.084 #####END data_diethylbenzidinehydrochloride _database_code_depnum_ccdc_archive 'CCDC 612089' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H88 Cl8 N8' _chemical_formula_weight 1253.02 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.648(3) _cell_length_b 16.387(3) _cell_length_c 8.3423(17) _cell_angle_alpha 90.00 _cell_angle_beta 102.936(4) _cell_angle_gamma 90.00 _cell_volume 1685.2(6) _cell_formula_units_Z 1 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2797 _cell_measurement_theta_min 2.797 _cell_measurement_theta_max 22.708 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.378 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8453 _exptl_absorpt_correction_T_max 0.9490 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12085 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2950 _reflns_number_gt 2179 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material 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^)+(0.0643P)^2^+1.1239P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2950 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 -0.01311(5) 0.50272(4) 0.24705(8) 0.0469(2) Uani 1 1 d . . . Cl2 Cl -0.00259(6) 0.23109(4) 0.21175(10) 0.0520(2) Uani 1 1 d . . . N1 N -0.89158(17) 0.36766(14) -0.5301(3) 0.0488(6) Uani 1 1 d . . . H1A H -0.9274 0.3858 -0.4568 0.073 Uiso 1 1 d R . . H1B H -0.9057 0.3149 -0.5490 0.073 Uiso 1 1 d R . . H1C H -0.9125 0.3955 -0.6235 0.073 Uiso 1 1 d R . . N2 N -0.10191(16) 0.37746(14) -0.0292(3) 0.0441(6) Uani 1 1 d . . . H2A H -0.0650 0.3887 -0.1057 0.066 Uiso 1 1 d R . . H2B H -0.0874 0.3267 0.0068 0.066 Uiso 1 1 d R . . H2C H -0.0825 0.4121 0.0544 0.066 Uiso 1 1 d R . . C1 C -0.7740(2) 0.37894(17) -0.4653(4) 0.0438(7) Uani 1 1 d . . . C2 C -0.6996(2) 0.3553(2) -0.5563(4) 0.0540(8) Uani 1 1 d . . . C3 C -0.5907(2) 0.36540(19) -0.4810(4) 0.0522(8) Uani 1 1 d . . . H3A H -0.5389 0.3506 -0.5391 0.063 Uiso 1 1 d R . . C4 C -0.5555(2) 0.39644(18) -0.3241(3) 0.0455(7) Uani 1 1 d . . . C5 C -0.4371(2) 0.39787(17) -0.2448(3) 0.0435(7) Uani 1 1 d . . . C6 C -0.3601(2) 0.41530(19) -0.3345(3) 0.0486(7) Uani 1 1 d . . . H6A H -0.3819 0.4316 -0.4438 0.058 Uiso 1 1 d R . . C7 C -0.2511(2) 0.40840(18) -0.2625(3) 0.0478(7) Uani 1 1 d . . . H7A H -0.1995 0.4192 -0.3234 0.057 Uiso 1 1 d R . . C8 C -0.2190(2) 0.38555(16) -0.1002(3) 0.0411(6) Uani 1 1 d . . . C9 C -0.2928(2) 0.37084(19) -0.0039(3) 0.0493(7) Uani 1 1 d . . . C10 C -0.4018(2) 0.37732(18) -0.0807(4) 0.0504(7) Uani 1 1 d . . . H10A H -0.4533 0.3673 -0.0191 0.060 Uiso 1 1 d R . . C11 C -0.6330(2) 0.4210(2) -0.2404(4) 0.0529(8) Uani 1 1 d . . . H11A H -0.6116 0.4433 -0.1356 0.063 Uiso 1 1 d R . . C12 C -0.7417(2) 0.41213(19) -0.3112(4) 0.0531(8) Uani 1 1 d . . . H12A H -0.7934 0.4287 -0.2543 0.064 Uiso 1 1 d R . . C13 C -0.7319(3) 0.3184(3) -0.7267(4) 0.0883(14) Uani 1 1 d . . . H13A H -0.7903 0.2808 -0.7273 0.106 Uiso 1 1 d R . . H13B H -0.6712 0.2873 -0.7445 0.106 Uiso 1 1 d R . . C14 C -0.7647(6) 0.3715(4) -0.8616(8) 0.0786(19) Uani 0.60 1 d P . . H14A H -0.7828 0.3414 -0.9628 0.118 Uiso 0.60 1 d PR . . H14B H -0.8269 0.4019 -0.8476 0.118 Uiso 0.60 1 d PR . . H14C H -0.7063 0.4085 -0.8649 0.118 Uiso 0.60 1 d PR . . C14' C -0.6745(13) 0.3526(9) -0.8443(15) 0.126(5) Uani 0.40 1 d P . . H14D H -0.6965 0.3261 -0.9492 0.189 Uiso 0.40 1 d PR . . H14E H -0.6937 0.4093 -0.8554 0.189 Uiso 0.40 1 d PR . . H14F H -0.5974 0.3474 -0.8056 0.189 Uiso 0.40 1 d PR . . C15 C -0.2559(3) 0.3471(3) 0.1749(4) 0.0780(11) Uani 1 1 d . . . H15A H -0.2100 0.2993 0.1806 0.094 Uiso 1 1 d R . . H15B H -0.2111 0.3909 0.2318 0.094 Uiso 1 1 d R . . C16 C -0.3389(4) 0.3296(3) 0.2648(5) 0.0956(14) Uani 1 1 d . . . H16A H -0.3054 0.3156 0.3763 0.143 Uiso 1 1 d R . . H16B H -0.3823 0.2846 0.2135 0.143 Uiso 1 1 d R . . H16C H -0.3840 0.3767 0.2637 0.143 Uiso 1 1 d 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 Cl1 0.0414(4) 0.0467(4) 0.0527(4) 0.0017(3) 0.0109(3) 0.0023(3) Cl2 0.0489(4) 0.0480(4) 0.0609(5) 0.0028(3) 0.0163(3) 0.0019(3) N1 0.0318(12) 0.0597(15) 0.0517(15) 0.0123(11) 0.0024(10) -0.0021(10) N2 0.0299(12) 0.0569(15) 0.0442(13) -0.0013(11) 0.0054(10) 0.0013(10) C1 0.0275(13) 0.0502(16) 0.0493(17) 0.0105(13) -0.0004(12) 0.0008(11) C2 0.0385(16) 0.078(2) 0.0445(17) 0.0021(15) 0.0069(13) -0.0099(15) C3 0.0338(15) 0.078(2) 0.0451(17) -0.0032(15) 0.0104(13) -0.0055(14) C4 0.0323(14) 0.0544(17) 0.0478(17) 0.0029(13) 0.0045(12) 0.0016(12) C5 0.0305(14) 0.0517(17) 0.0463(16) -0.0037(13) 0.0046(12) 0.0021(12) C6 0.0360(15) 0.0653(19) 0.0421(16) 0.0056(14) 0.0036(12) -0.0020(13) C7 0.0335(14) 0.0646(19) 0.0455(16) 0.0012(14) 0.0089(12) -0.0060(13) C8 0.0275(13) 0.0493(16) 0.0447(16) -0.0045(12) 0.0041(11) -0.0006(11) C9 0.0345(15) 0.072(2) 0.0417(16) 0.0036(14) 0.0085(12) 0.0054(13) C10 0.0311(14) 0.075(2) 0.0460(17) 0.0036(14) 0.0112(12) 0.0018(13) C11 0.0367(16) 0.069(2) 0.0498(17) -0.0099(15) 0.0039(13) 0.0089(14) C12 0.0303(15) 0.067(2) 0.061(2) -0.0064(16) 0.0085(13) 0.0089(13) C13 0.056(2) 0.151(4) 0.058(2) -0.023(3) 0.0128(18) -0.037(2) C14 0.079(5) 0.091(5) 0.063(4) 0.000(3) 0.011(4) -0.003(4) C14' 0.144(13) 0.178(14) 0.072(8) -0.043(8) 0.057(9) -0.063(11) C15 0.0429(19) 0.138(3) 0.053(2) 0.022(2) 0.0105(15) 0.009(2) C16 0.101(3) 0.124(4) 0.066(3) 0.022(2) 0.028(2) 0.000(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 N1 C1 1.476(3) . ? N1 H1A 0.8901 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 C8 1.472(3) . ? N2 H2A 0.8901 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? C1 C12 1.371(4) . ? C1 C2 1.389(4) . ? C2 C3 1.390(4) . ? C2 C13 1.515(5) . ? C3 C4 1.382(4) . ? C3 H3A 0.9300 . ? C4 C11 1.384(4) . ? C4 C5 1.495(4) . ? C5 C10 1.383(4) . ? C5 C6 1.385(4) . ? C6 C7 1.379(4) . ? C6 H6A 0.9300 . ? C7 C8 1.376(4) . ? C7 H7A 0.9300 . ? C8 C9 1.382(4) . ? C9 C10 1.389(4) . ? C9 C15 1.510(4) . ? C10 H10A 0.9302 . ? C11 C12 1.378(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9299 . ? C13 C14 1.410(7) . ? C13 C14' 1.457(12) . ? C13 H13A 0.9601 . ? C13 H13B 0.9600 . ? C14 C14' 1.160(15) . ? C14 H14A 0.9600 . ? C14 H14B 0.9602 . ? C14 H14C 0.9600 . ? C14 H14D 1.4530 . ? C14 H14E 1.0826 . ? C14' H13B 1.3504 . ? C14' H14A 1.5103 . ? C14' H14C 0.9997 . ? C14' H14D 0.9599 . ? C14' H14E 0.9601 . ? C14' H14F 0.9600 . ? C15 C16 1.449(5) . ? C15 H15A 0.9699 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 H1A 109.5 . . ? C1 N1 H1B 109.4 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C8 N2 H2A 109.5 . . ? C8 N2 H2B 109.4 . . ? H2A N2 H2B 109.5 . . ? C8 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C12 C1 C2 121.8(2) . . ? C12 C1 N1 117.2(3) . . ? C2 C1 N1 121.0(3) . . ? C1 C2 C3 116.4(3) . . ? C1 C2 C13 123.4(3) . . ? C3 C2 C13 120.2(3) . . ? C4 C3 C2 123.2(3) . . ? C4 C3 H3A 118.4 . . ? C2 C3 H3A 118.4 . . ? C3 C4 C11 118.1(3) . . ? C3 C4 C5 120.2(3) . . ? C11 C4 C5 121.6(3) . . ? C10 C5 C6 118.4(2) . . ? C10 C5 C4 120.2(2) . . ? C6 C5 C4 121.3(2) . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.1 . . ? C7 C8 C9 122.0(2) . . ? C7 C8 N2 118.0(2) . . ? C9 C8 N2 120.0(2) . . ? C8 C9 C10 116.6(3) . . ? C8 C9 C15 121.3(3) . . ? C10 C9 C15 122.1(3) . . ? C5 C10 C9 122.9(3) . . ? C5 C10 H10A 118.6 . . ? C9 C10 H10A 118.5 . . ? C12 C11 C4 120.3(3) . . ? C12 C11 H11A 119.8 . . ? C4 C11 H11A 119.9 . . ? C1 C12 C11 120.2(3) . . ? C1 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C14' 47.7(7) . . ? C14 C13 C2 118.1(5) . . ? C14' C13 C2 114.1(5) . . ? C14 C13 H13A 107.6 . . ? C14' C13 H13A 137.8 . . ? C2 C13 H13A 107.9 . . ? C14 C13 H13B 107.8 . . ? C14' C13 H13B 64.1 . . ? C2 C13 H13B 107.5 . . ? H13A C13 H13B 107.4 . . ? C14' C14 C13 68.3(8) . . ? C14' C14 H14A 90.4 . . ? C13 C14 H14A 110.7 . . ? C14' C14 H14B 159.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 109.5 . . ? C14' C14 H14C 55.3 . . ? C13 C14 H14C 108.7 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C14' C14 H14D 41.2 . . ? C13 C14 H14D 89.1 . . ? H14A C14 H14D 49.2 . . ? H14B C14 H14D 157.1 . . ? H14C C14 H14D 76.2 . . ? C14' C14 H14E 50.6 . . ? C13 C14 H14E 102.8 . . ? H14A C14 H14E 111.6 . . ? H14B C14 H14E 113.0 . . ? H14C C14 H14E 6.0 . . ? H14D C14 H14E 74.8 . . ? C14 C14' C13 64.0(7) . . ? C14 C14' H13B 100.5 . . ? C13 C14' H13B 39.8 . . ? C14 C14' H14A 39.5 . . ? C13 C14' H14A 83.0 . . ? H13B C14' H14A 101.9 . . ? C14 C14' H14C 52.1 . . ? C13 C14' H14C 103.0 . . ? H13B C14' H14C 141.9 . . ? H14A C14' H14C 74.2 . . ? C14 C14' H14D 86.0 . . ? C13 C14' H14D 110.7 . . ? H13B C14' H14D 99.6 . . ? H14A C14' H14D 46.6 . . ? H14C C14' H14D 103.5 . . ? C14 C14' H14E 60.5 . . ? C13 C14' H14E 106.5 . . ? H13B C14' H14E 143.0 . . ? H14A C14' H14E 83.2 . . ? H14C C14' H14E 9.2 . . ? H14D C14' H14E 109.5 . . ? C14 C14' H14F 164.2 . . ? C13 C14' H14F 111.2 . . ? H13B C14' H14F 80.5 . . ? H14A C14' H14F 156.1 . . ? H14C C14' H14F 118.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? C16 C15 C9 117.5(3) . . ? C16 C15 H15A 108.0 . . ? C9 C15 H15A 107.8 . . ? C16 C15 H15B 107.8 . . ? C9 C15 H15B 108.1 . . ? H15A C15 H15B 107.2 . . ? C15 C16 H16A 109.6 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 H2A Cl1 0.89 2.46 3.234(2) 145.5 3_565 N2 H2A Cl2 0.89 2.71 3.260(2) 121.3 4_565 N2 H2B Cl2 0.89 2.39 3.200(2) 151.7 . N2 H2C Cl1 0.89 2.22 3.103(2) 171.5 . N1 H1A Cl2 0.89 2.67 3.151(2) 114.7 4_465 N1 H1A Cl1 0.89 2.75 3.580(3) 156.0 3_465 N1 H1B Cl2 0.89 2.50 3.204(3) 135.8 1_454 N1 H1C Cl1 0.89 2.29 3.072(2) 146.0 1_454 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.472 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.051