# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 880352' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H13 Cd Cl2 N O6' _chemical_formula_weight 414.50 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 15.158(5) _cell_length_b 12.517(4) _cell_length_c 7.440(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.12(3) _cell_angle_gamma 90.00 _cell_volume 1409.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.1126 _cell_measurement_theta_max 27.5359 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.953 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 1.947 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5739 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _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 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8762 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2414 _reflns_number_gt 1984 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2002)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2002)' _computing_structure_solution 'Siemens SHELXTL^TM^ 5' _computing_structure_refinement 'Siemens SHELXTL^TM^ 5' _computing_molecular_graphics ? _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0632P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2414 _refine_ls_number_parameters 184 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.002 _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 0.944867(19) 0.86920(2) 0.03135(4) 0.03090(10) Uani 1 1 d . . . Cl2 Cl 1.10204(6) 0.94144(8) 0.08689(16) 0.0370(3) Uani 1 1 d . . . Cl1 Cl 0.97771(8) 0.68738(8) 0.18913(15) 0.0396(3) Uani 1 1 d . . . O2W O 0.80035(19) 0.8268(3) -0.0080(4) 0.0476(9) Uani 1 1 d D . . H2WA H 0.7744(17) 0.841(2) -0.108(2) 0.057 Uiso 1 1 d D . . H2WB H 0.7771(16) 0.7699(13) 0.029(4) 0.057 Uiso 1 1 d D . . O1W O 0.9099(2) 0.9417(3) 0.3214(4) 0.0486(9) Uani 1 1 d D . . H1WA H 0.911(3) 0.8932(10) 0.400(2) 0.058 Uiso 1 1 d D . . H1WB H 0.913(3) 1.0009(9) 0.375(3) 0.058 Uiso 1 1 d D . . O4 O 0.7257(2) 0.8486(2) 0.6423(4) 0.0401(8) Uani 1 1 d . . . O3 O 0.6124(2) 0.9620(2) 0.6190(4) 0.0443(8) Uani 1 1 d . . . H3B H 0.6223 0.9682 0.7279 0.066 Uiso 1 1 calc R . . N1 N 0.6460(2) 1.0705(3) 0.2726(5) 0.0388(10) Uani 1 1 d . . . O2 O 0.5605(2) 0.8431(3) 0.0047(4) 0.0514(9) Uani 1 1 d . . . O1 O 0.6246(2) 0.9972(2) -0.0601(4) 0.0495(9) Uani 1 1 d . . . C7 C 0.6059(3) 0.9599(3) 0.2459(6) 0.0381(11) Uani 1 1 d . . . H7A H 0.5469 0.9613 0.2936 0.046 Uiso 1 1 calc R . . C9 C 0.6689(3) 0.8974(3) 0.5553(6) 0.0323(10) Uani 1 1 d . . . C1 C 0.7306(3) 1.0900(4) 0.2402(6) 0.0460(13) Uani 1 1 d . . . H1A H 0.7671 1.0344 0.2075 0.055 Uiso 1 1 calc R . . C2 C 0.7637(3) 1.1928(4) 0.2556(6) 0.0484(13) Uani 1 1 d . . . H2A H 0.8228 1.2063 0.2360 0.058 Uiso 1 1 calc R . . C8 C 0.6594(4) 0.8796(4) 0.3509(6) 0.0466(13) Uani 1 1 d . . . H8A H 0.7181 0.8780 0.3050 0.056 Uiso 1 1 calc R . . H8B H 0.6331 0.8098 0.3289 0.056 Uiso 1 1 calc R . . C4 C 0.6216(3) 1.2526(4) 0.3318(6) 0.0429(12) Uani 1 1 d . . . H4A H 0.5829 1.3068 0.3610 0.051 Uiso 1 1 calc R . . C3 C 0.7079(3) 1.2762(4) 0.3005(6) 0.0447(12) Uani 1 1 d . . . H3A H 0.7286 1.3461 0.3091 0.054 Uiso 1 1 calc R . . C5 C 0.5925(3) 1.1497(3) 0.3199(6) 0.0389(12) Uani 1 1 d . . . H5A H 0.5345 1.1341 0.3451 0.047 Uiso 1 1 calc R . . C6 C 0.5952(3) 0.9280(4) 0.0481(6) 0.0344(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03217(17) 0.02277(16) 0.0374(2) 0.00253(13) -0.00124(14) -0.00337(12) Cl2 0.0289(5) 0.0244(5) 0.0569(7) 0.0043(5) -0.0038(5) 0.0004(4) Cl1 0.0574(7) 0.0269(5) 0.0341(6) 0.0072(5) -0.0009(5) 0.0004(5) O2W 0.0386(17) 0.0582(19) 0.044(2) 0.0224(16) -0.0172(14) -0.0185(15) O1W 0.059(2) 0.0459(18) 0.040(2) 0.0012(16) -0.0004(17) 0.0079(17) O4 0.0459(17) 0.0444(17) 0.0289(17) -0.0015(14) -0.0086(14) 0.0137(14) O3 0.0529(18) 0.0530(19) 0.0275(17) 0.0068(14) 0.0064(14) 0.0179(15) N1 0.051(2) 0.0233(17) 0.044(2) -0.0029(16) 0.0160(18) -0.0010(16) O2 0.065(2) 0.053(2) 0.0361(19) -0.0043(16) 0.0035(16) -0.0172(17) O1 0.075(2) 0.0328(16) 0.0415(19) -0.0063(16) 0.0090(16) -0.0034(16) C7 0.041(2) 0.037(2) 0.037(3) -0.005(2) 0.003(2) -0.0015(19) C9 0.038(2) 0.035(2) 0.024(2) 0.0052(19) 0.0048(18) 0.0025(19) C1 0.045(3) 0.037(2) 0.057(3) -0.004(2) 0.013(2) 0.016(2) C2 0.032(2) 0.063(3) 0.049(3) 0.000(3) 0.001(2) -0.005(2) C8 0.066(3) 0.043(3) 0.031(3) 0.004(2) 0.003(2) 0.011(2) C4 0.044(2) 0.036(2) 0.048(3) -0.007(2) 0.000(2) 0.010(2) C3 0.056(3) 0.028(2) 0.050(3) -0.013(2) 0.002(2) -0.008(2) C5 0.035(2) 0.042(2) 0.041(3) -0.009(2) 0.010(2) -0.0007(19) C6 0.034(2) 0.045(3) 0.024(2) -0.007(2) 0.0002(18) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O2W 2.258(3) . ? Cd1 O1W 2.426(3) . ? Cd1 Cl2 2.5607(13) . ? Cd1 Cl1 2.5964(12) . ? Cd1 Cl2 2.6133(13) 3_775 ? Cd1 Cl1 2.7148(14) 4_575 ? Cl2 Cd1 2.6133(13) 3_775 ? Cl1 Cd1 2.7148(14) 4_576 ? O2W H2WA 0.842(9) . ? O2W H2WB 0.847(9) . ? O1W H1WA 0.844(9) . ? O1W H1WB 0.843(9) . ? O4 C9 1.214(5) . ? O3 C9 1.287(5) . ? O3 H3B 0.8200 . ? N1 C5 1.340(5) . ? N1 C1 1.340(6) . ? N1 C7 1.521(5) . ? O2 C6 1.222(5) . ? O1 C6 1.279(5) . ? C7 C8 1.487(6) . ? C7 C6 1.525(6) . ? C7 H7A 0.9800 . ? C9 C8 1.536(6) . ? C1 C2 1.384(7) . ? C1 H1A 0.9300 . ? C2 C3 1.396(7) . ? C2 H2A 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 C5 1.362(6) . ? C4 C3 1.374(7) . ? C4 H4A 0.9300 . ? C3 H3A 0.9300 . ? C5 H5A 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 O2W Cd1 O1W 86.90(12) . . ? O2W Cd1 Cl2 172.60(9) . . ? O1W Cd1 Cl2 88.32(9) . . ? O2W Cd1 Cl1 90.78(9) . . ? O1W Cd1 Cl1 88.36(8) . . ? Cl2 Cd1 Cl1 94.75(4) . . ? O2W Cd1 Cl2 85.71(9) . 3_775 ? O1W Cd1 Cl2 83.78(8) . 3_775 ? Cl2 Cd1 Cl2 88.15(4) . 3_775 ? Cl1 Cd1 Cl2 171.55(4) . 3_775 ? O2W Cd1 Cl1 92.47(9) . 4_575 ? O1W Cd1 Cl1 172.71(8) . 4_575 ? Cl2 Cd1 Cl1 91.55(4) . 4_575 ? Cl1 Cd1 Cl1 98.91(3) . 4_575 ? Cl2 Cd1 Cl1 88.93(4) 3_775 4_575 ? Cd1 Cl2 Cd1 91.85(4) . 3_775 ? Cd1 Cl1 Cd1 127.75(4) . 4_576 ? Cd1 O2W H2WA 117.9(19) . . ? Cd1 O2W H2WB 125.0(18) . . ? H2WA O2W H2WB 106(2) . . ? Cd1 O1W H1WA 110.6(16) . . ? Cd1 O1W H1WB 138(2) . . ? H1WA O1W H1WB 107.7(18) . . ? C9 O3 H3B 109.5 . . ? C5 N1 C1 120.8(4) . . ? C5 N1 C7 117.6(4) . . ? C1 N1 C7 121.5(4) . . ? C8 C7 N1 110.1(4) . . ? C8 C7 C6 110.8(4) . . ? N1 C7 C6 112.7(4) . . ? C8 C7 H7A 107.7 . . ? N1 C7 H7A 107.7 . . ? C6 C7 H7A 107.7 . . ? O4 C9 O3 126.0(4) . . ? O4 C9 C8 118.7(4) . . ? O3 C9 C8 115.3(4) . . ? N1 C1 C2 120.0(4) . . ? N1 C1 H1A 120.0 . . ? C2 C1 H1A 120.0 . . ? C1 C2 C3 119.6(4) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C7 C8 C9 116.1(4) . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8B 108.3 . . ? C9 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C4 C3 C2 118.3(4) . . ? C4 C3 H3A 120.8 . . ? C2 C3 H3A 120.8 . . ? N1 C5 C4 121.2(4) . . ? N1 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? O2 C6 O1 125.6(4) . . ? O2 C6 C7 120.3(4) . . ? O1 C6 C7 114.1(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 O2W H2WB O4 0.847(9) 1.894(11) 2.736(4) 172(3) 4_575 O2W H2WA O4 0.842(9) 1.963(12) 2.793(4) 168(3) 1_554 O3 H3B O1 0.82 1.62 2.425(4) 168.1 1_556 O1W H1WA Cl1 0.844(9) 2.54(2) 3.293(3) 150(4) 4_576 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.745 _refine_diff_density_min -1.015 _refine_diff_density_rms 0.117 data_2 _database_code_depnum_ccdc_archive 'CCDC 880353' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'Br2 Cd H4 O2, C9 H9 N O4' _chemical_formula_sum 'C9 H13 Br2 Cd N O6' _chemical_formula_weight 503.42 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' Br Br -0.2901 2.4595 '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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.012(2) _cell_length_b 12.510(6) _cell_length_c 14.753(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1478.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.1322 _cell_measurement_theta_max 27.4642 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 6.900 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4943 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _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 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9614 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.0957 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2709 _reflns_number_gt 1752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2002)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2002)' _computing_structure_solution 'Siemens SHELXTL^TM^ 5' _computing_structure_refinement 'Siemens SHELXTL^TM^ 5' _computing_molecular_graphics ? _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0025(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 2709 _refine_ls_number_parameters 185 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1401 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.004 _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 0.31657(9) 0.75475(4) 0.50327(5) 0.04113(18) Uani 1 1 d . . . O2W O 0.2936(8) 0.7182(4) 0.6568(4) 0.0536(19) Uani 1 1 d D . . H2WA H 0.292(6) 0.7813(8) 0.6782(18) 0.080 Uiso 1 1 d D . . H2WB H 0.244(3) 0.6808(16) 0.6965(15) 0.080 Uiso 1 1 d D . . O1W O 0.3481(6) 0.8010(4) 0.3536(4) 0.0498(18) Uani 1 1 d D . . H1WA H 0.4274(15) 0.832(2) 0.325(2) 0.075 Uiso 1 1 d D . . H1WB H 0.2610(13) 0.833(2) 0.334(3) 0.075 Uiso 1 1 d D . . O2 O 0.4109(7) 0.8980(5) 0.8006(4) 0.062(2) Uani 1 1 d . . . O1 O 0.5250(6) 1.0562(4) 0.7637(4) 0.0507(18) Uani 1 1 d . . . C8 C 0.8431(9) 0.9724(7) 0.7766(6) 0.060(3) Uani 1 1 d . . . H8A H 0.8375 1.0237 0.8259 0.072 Uiso 1 1 calc R . . H8B H 0.8329 1.0119 0.7204 0.072 Uiso 1 1 calc R . . C7 C 0.7048(11) 0.9024(7) 0.7840(7) 0.059(3) Uani 1 1 d . . . H7A H 0.7055 0.8568 0.7300 0.071 Uiso 1 1 calc R . . C6 C 0.5334(10) 0.9630(7) 0.7848(6) 0.044(3) Uani 1 1 d . . . C5 C 0.6886(11) 0.7226(7) 0.8488(6) 0.054(3) Uani 1 1 d . . . H5A H 0.6728 0.7003 0.7893 0.065 Uiso 1 1 calc R . . O4 O 1.0393(7) 0.8216(4) 0.7690(4) 0.0497(18) Uani 1 1 d . . . N1 N 0.7073(9) 0.8272(6) 0.8674(5) 0.049(2) Uani 1 1 d . . . O3 O 1.1348(7) 0.9848(5) 0.7961(4) 0.059(2) Uani 1 1 d . . . H3B H 1.2254 0.9543 0.7972 0.088 Uiso 1 1 calc R . . C3 C 0.7108(12) 0.6845(8) 1.0068(7) 0.0691(9) Uani 1 1 d U . . H3A H 0.7119 0.6365 1.0550 0.083 Uiso 1 1 calc R . . C9 C 1.0204(10) 0.9173(7) 0.7788(6) 0.048(3) Uani 1 1 d . . . C4 C 0.6928(14) 0.6465(9) 0.9196(7) 0.0767(9) Uani 1 1 d U . . H4A H 0.6838 0.5737 0.9078 0.092 Uiso 1 1 calc R . . C1 C 0.7225(12) 0.8613(8) 0.9546(7) 0.068(3) Uani 1 1 d . . . H1A H 0.7299 0.9340 0.9671 0.082 Uiso 1 1 calc R . . C2 C 0.7269(15) 0.7894(10) 1.0233(8) 0.0931(9) Uani 1 1 d U . . H2A H 0.7412 0.8131 1.0825 0.112 Uiso 1 1 calc R . . Br2 Br 0.06066(11) 0.90082(7) 0.51968(6) 0.0476(3) Uani 1 1 d . . . Br1 Br 0.57509(11) 0.89664(7) 0.53979(6) 0.0438(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0306(3) 0.0414(4) 0.0514(4) 0.0011(3) 0.0009(3) 0.0002(3) O2W 0.065(4) 0.039(3) 0.057(4) 0.003(3) 0.002(4) 0.014(3) O1W 0.050(4) 0.055(4) 0.045(4) -0.009(3) 0.004(3) 0.001(3) O2 0.034(3) 0.059(4) 0.092(5) 0.020(4) 0.007(4) -0.001(4) O1 0.026(3) 0.045(3) 0.081(4) 0.007(3) -0.007(3) 0.007(3) C8 0.035(5) 0.073(7) 0.073(7) 0.013(6) 0.015(5) 0.004(5) C7 0.049(5) 0.047(5) 0.080(7) 0.019(5) 0.000(6) 0.020(5) C6 0.026(5) 0.052(5) 0.054(6) 0.006(4) -0.007(4) 0.006(4) C5 0.043(5) 0.056(6) 0.062(6) -0.018(5) 0.000(5) 0.003(5) O4 0.034(3) 0.032(3) 0.084(4) -0.011(3) 0.001(3) 0.001(3) N1 0.037(4) 0.059(5) 0.051(5) 0.008(4) 0.003(4) 0.003(4) O3 0.033(3) 0.054(4) 0.089(5) -0.011(4) -0.012(3) 0.003(3) C3 0.0692(11) 0.0692(11) 0.0689(12) 0.0006(8) 0.0000(8) 0.0001(8) C9 0.023(4) 0.069(7) 0.051(6) -0.008(5) -0.002(4) -0.006(5) C4 0.0766(11) 0.0767(11) 0.0768(12) 0.0001(8) 0.0002(8) 0.0000(8) C1 0.055(7) 0.055(6) 0.095(8) -0.016(6) -0.001(6) 0.004(5) C2 0.0929(11) 0.0933(11) 0.0930(12) -0.0002(8) -0.0001(8) 0.0000(8) Br2 0.0331(4) 0.0356(5) 0.0740(6) -0.0020(4) 0.0005(5) -0.0001(5) Br1 0.0352(4) 0.0387(5) 0.0575(5) -0.0046(4) 0.0007(5) 0.0002(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 Cd1 O1W 2.297(5) . ? Cd1 O2W 2.318(5) . ? Cd1 Br2 2.7570(13) . ? Cd1 Br2 2.7797(13) 4_566 ? Cd1 Br1 2.7804(13) . ? Cd1 Br1 2.7809(13) 4_466 ? O2W H2WA 0.850(9) . ? O2W H2WB 0.850(10) . ? O1W H1WA 0.850(10) . ? O1W H1WB 0.850(10) . ? O2 C6 1.296(10) . ? O1 C6 1.209(9) . ? C8 C7 1.416(12) . ? C8 C9 1.579(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 N1 1.548(11) . ? C7 C6 1.569(11) . ? C7 H7A 0.9800 . ? C5 N1 1.346(10) . ? C5 C4 1.413(13) . ? C5 H5A 0.9300 . ? O4 C9 1.216(10) . ? N1 C1 1.361(12) . ? O3 C9 1.272(9) . ? O3 H3B 0.8200 . ? C3 C2 1.341(15) . ? C3 C4 1.380(14) . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? C1 C2 1.355(15) . ? C1 H1A 0.9300 . ? C2 H2A 0.9300 . ? Br2 Cd1 2.7797(13) 4_466 ? Br1 Cd1 2.7809(13) 4_566 ? 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 O1W Cd1 O2W 176.29(19) . . ? O1W Cd1 Br2 89.96(13) . . ? O2W Cd1 Br2 89.20(14) . . ? O1W Cd1 Br2 88.97(14) . 4_566 ? O2W Cd1 Br2 92.10(14) . 4_566 ? Br2 Cd1 Br2 176.30(4) . 4_566 ? O1W Cd1 Br1 86.75(13) . . ? O2W Cd1 Br1 89.75(15) . . ? Br2 Cd1 Br1 96.54(4) . . ? Br2 Cd1 Br1 86.93(4) 4_566 . ? O1W Cd1 Br1 91.64(13) . 4_466 ? O2W Cd1 Br1 91.93(14) . 4_466 ? Br2 Cd1 Br1 87.37(4) . 4_466 ? Br2 Cd1 Br1 89.13(4) 4_566 4_466 ? Br1 Cd1 Br1 175.77(4) . 4_466 ? Cd1 O2W H2WA 100.4(19) . . ? Cd1 O2W H2WB 145.1(19) . . ? H2WA O2W H2WB 104(2) . . ? Cd1 O1W H1WA 132(2) . . ? Cd1 O1W H1WB 110(2) . . ? H1WA O1W H1WB 104.0(18) . . ? C7 C8 C9 115.6(8) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.4 . . ? C8 C7 N1 115.2(8) . . ? C8 C7 C6 112.7(7) . . ? N1 C7 C6 107.4(7) . . ? C8 C7 H7A 107.0 . . ? N1 C7 H7A 107.0 . . ? C6 C7 H7A 107.0 . . ? O1 C6 O2 127.5(7) . . ? O1 C6 C7 120.9(7) . . ? O2 C6 C7 111.1(7) . . ? N1 C5 C4 120.1(9) . . ? N1 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 N1 C1 120.5(8) . . ? C5 N1 C7 115.3(7) . . ? C1 N1 C7 124.2(8) . . ? C9 O3 H3B 109.5 . . ? C2 C3 C4 121.1(10) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? O4 C9 O3 126.0(8) . . ? O4 C9 C8 122.7(7) . . ? O3 C9 C8 111.3(7) . . ? C3 C4 C5 117.4(10) . . ? C3 C4 H4A 121.3 . . ? C5 C4 H4A 121.3 . . ? C2 C1 N1 120.1(10) . . ? C2 C1 H1A 119.9 . . ? N1 C1 H1A 119.9 . . ? C3 C2 C1 120.8(11) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? Cd1 Br2 Cd1 92.78(4) . 4_466 ? Cd1 Br1 Cd1 92.25(4) . 4_566 ? 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 O3 H3B O2 0.82 1.65 2.465(8) 177.6 1_655 O1W H1WA O4 0.850(10) 2.53(3) 2.823(8) 101(2) 4_466 O1W H1WA O3 0.850(10) 2.39(3) 2.814(8) 111(2) 2_674 O2W H2WB O1 0.850(10) 2.49(3) 2.755(7) 99.2(19) 3_646 O2W H2WA O4 0.850(9) 2.48(4) 2.927(8) 114(3) 1_455 O2W H2WA O2 0.850(9) 2.51(3) 3.232(8) 143(4) . C1 H1A Br1 0.93 2.84 3.658(10) 147.0 2_675 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.707 _refine_diff_density_min -1.204 _refine_diff_density_rms 0.197