# Electronic Supplementary Material (ESI) for RSC Advances # 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_szg182 _database_code_depnum_ccdc_archive 'CCDC 874503' #TrackingRef 'szg182.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N O5 P Zn' _chemical_formula_weight 308.52 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pca2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 9.9240(11) _cell_length_b 12.4951(14) _cell_length_c 8.6343(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1070.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1076 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 24.91 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.914 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 2.452 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8872 _exptl_absorpt_correction_T_max 0.9759 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5792 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0757 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 26.49 _reflns_number_total 2075 _reflns_number_gt 1627 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0350P)^2^+0.7709P] 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 -0.01(3) _refine_ls_number_reflns 2075 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Zn1 Zn 0.07827(6) 1.12038(5) 0.69048(8) 0.01918(18) Uani 1 1 d . . . P1 P -0.14326(16) 0.97163(13) 0.8361(2) 0.0163(4) Uani 1 1 d . . . O1 O -0.0946(4) 1.0783(4) 0.7737(5) 0.0252(11) Uani 1 1 d . . . O2 O -0.2946(4) 0.9630(3) 0.8208(6) 0.0236(10) Uani 1 1 d . . . O3 O -0.0922(5) 0.9549(4) 0.9973(5) 0.0316(13) Uani 1 1 d . . . O4 O 0.1340(5) 0.2684(3) 0.7083(7) 0.0335(12) Uani 1 1 d . . . O5 O -0.0199(6) 0.2871(4) 0.5252(7) 0.0428(15) Uani 1 1 d . . . N1 N 0.0720(5) 0.8406(4) 0.7593(6) 0.0220(13) Uani 1 1 d . . . H1C H 0.1137 0.9028 0.7808 0.026 Uiso 1 1 calc R . . H1D H 0.0725 0.8009 0.8463 0.026 Uiso 1 1 calc R . . C1 C -0.0723(6) 0.8643(5) 0.7169(9) 0.0216(18) Uani 1 1 d . . . H1A H -0.1259 0.8001 0.7300 0.026 Uiso 1 1 calc R . . H1B H -0.0767 0.8850 0.6087 0.026 Uiso 1 1 calc R . . C2 C 0.1518(7) 0.7828(5) 0.6375(8) 0.0237(16) Uani 1 1 d . . . H2A H 0.1297 0.8130 0.5371 0.028 Uiso 1 1 calc R . . H2B H 0.2469 0.7955 0.6559 0.028 Uiso 1 1 calc R . . C3 C 0.1284(7) 0.6646(5) 0.6317(7) 0.0193(15) Uani 1 1 d . . . C4 C 0.2118(6) 0.5954(5) 0.7138(10) 0.0260(18) Uani 1 1 d . . . H4A H 0.2813 0.6233 0.7738 0.031 Uiso 1 1 calc R . . C5 C 0.1930(6) 0.4856(5) 0.7077(12) 0.0297(17) Uani 1 1 d . . . H5A H 0.2498 0.4404 0.7631 0.036 Uiso 1 1 calc R . . C6 C 0.0898(7) 0.4431(5) 0.6191(8) 0.0228(16) Uani 1 1 d . . . C7 C 0.0084(8) 0.5124(6) 0.5367(9) 0.0307(18) Uani 1 1 d . . . H7A H -0.0598 0.4841 0.4752 0.037 Uiso 1 1 calc R . . C8 C 0.0247(7) 0.6219(6) 0.5423(9) 0.0285(16) Uani 1 1 d . . . H8A H -0.0328 0.6667 0.4872 0.034 Uiso 1 1 calc R . . C9 C 0.0649(7) 0.3246(6) 0.6134(9) 0.0274(17) 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 Zn1 0.0196(3) 0.0138(3) 0.0242(3) 0.0007(5) 0.0011(5) -0.0002(3) P1 0.0161(8) 0.0127(8) 0.0201(9) 0.0001(7) -0.0007(7) 0.0010(7) O1 0.020(2) 0.019(2) 0.037(3) 0.004(2) 0.006(2) 0.005(2) O2 0.014(2) 0.020(2) 0.037(3) -0.006(2) -0.002(2) -0.0027(19) O3 0.042(3) 0.030(3) 0.023(3) 0.005(2) -0.012(2) 0.009(3) O4 0.040(3) 0.015(2) 0.046(3) 0.004(3) -0.002(3) -0.002(2) O5 0.045(3) 0.022(3) 0.061(4) -0.012(3) -0.008(3) -0.006(3) N1 0.019(3) 0.013(3) 0.034(3) -0.001(2) 0.000(3) 0.003(3) C1 0.017(3) 0.022(3) 0.026(5) -0.008(3) -0.004(3) 0.001(3) C2 0.023(3) 0.014(3) 0.035(4) -0.003(3) 0.011(3) 0.004(3) C3 0.021(3) 0.011(3) 0.026(4) -0.002(3) 0.005(3) -0.002(3) C4 0.020(3) 0.021(4) 0.037(5) -0.007(3) -0.001(4) -0.006(2) C5 0.028(3) 0.019(3) 0.043(5) 0.003(4) -0.008(4) 0.007(3) C6 0.028(4) 0.014(3) 0.026(4) -0.003(3) 0.006(3) 0.000(3) C7 0.031(4) 0.026(4) 0.035(4) -0.004(4) -0.006(4) -0.008(3) C8 0.028(4) 0.019(4) 0.038(4) -0.002(4) -0.005(3) 0.008(4) C9 0.030(4) 0.015(3) 0.037(4) -0.001(3) 0.010(4) 0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.920(4) 2_574 ? Zn1 O1 1.933(4) . ? Zn1 O4 1.936(4) 1_565 ? Zn1 O2 1.985(5) 3_575 ? P1 O3 1.495(5) . ? P1 O2 1.512(4) . ? P1 O1 1.517(5) . ? P1 C1 1.831(7) . ? O2 Zn1 1.985(5) 3_475 ? O3 Zn1 1.920(4) 2_575 ? O4 C9 1.279(9) . ? O4 Zn1 1.936(4) 1_545 ? O5 C9 1.228(8) . ? N1 C2 1.502(8) . ? N1 C1 1.507(8) . ? N1 H1C 0.9000 . ? N1 H1D 0.9000 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.495(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.391(9) . ? C3 C8 1.392(9) . ? C4 C5 1.386(8) . ? C4 H4A 0.9300 . ? C5 C6 1.384(10) . ? C5 H5A 0.9300 . ? C6 C7 1.381(10) . ? C6 C9 1.502(9) . ? C7 C8 1.379(9) . ? C7 H7A 0.9300 . ? C8 H8A 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 O3 Zn1 O1 104.7(2) 2_574 . ? O3 Zn1 O4 121.1(2) 2_574 1_565 ? O1 Zn1 O4 118.9(2) . 1_565 ? O3 Zn1 O2 100.9(2) 2_574 3_575 ? O1 Zn1 O2 102.13(19) . 3_575 ? O4 Zn1 O2 105.9(2) 1_565 3_575 ? O3 P1 O2 114.1(3) . . ? O3 P1 O1 110.2(3) . . ? O2 P1 O1 110.4(2) . . ? O3 P1 C1 106.9(3) . . ? O2 P1 C1 106.3(3) . . ? O1 P1 C1 108.7(3) . . ? P1 O1 Zn1 130.9(3) . . ? P1 O2 Zn1 135.9(3) . 3_475 ? P1 O3 Zn1 154.3(3) . 2_575 ? C9 O4 Zn1 108.7(5) . 1_545 ? C2 N1 C1 115.2(5) . . ? C2 N1 H1C 108.5 . . ? C1 N1 H1C 108.5 . . ? C2 N1 H1D 108.5 . . ? C1 N1 H1D 108.5 . . ? H1C N1 H1D 107.5 . . ? N1 C1 P1 111.9(4) . . ? N1 C1 H1A 109.2 . . ? P1 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? P1 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C3 C2 N1 114.6(5) . . ? C3 C2 H2A 108.6 . . ? N1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? N1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C8 119.0(6) . . ? C4 C3 C2 120.3(6) . . ? C8 C3 C2 120.8(6) . . ? C5 C4 C3 121.0(7) . . ? C5 C4 H4A 119.5 . . ? C3 C4 H4A 119.5 . . ? C6 C5 C4 120.0(7) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C7 C6 C5 118.5(6) . . ? C7 C6 C9 120.3(7) . . ? C5 C6 C9 121.2(6) . . ? C8 C7 C6 122.4(7) . . ? C8 C7 H7A 118.8 . . ? C6 C7 H7A 118.8 . . ? C7 C8 C3 119.1(7) . . ? C7 C8 H8A 120.5 . . ? C3 C8 H8A 120.5 . . ? O5 C9 O4 123.7(7) . . ? O5 C9 C6 120.6(7) . . ? O4 C9 C6 115.6(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.615 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.107 data_szg183 _database_code_depnum_ccdc_archive 'CCDC 874504' #TrackingRef 'szg183.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H11 Cd Cl N O5 P' _chemical_formula_weight 392.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' P P 0.1023 0.0942 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' 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' '-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 7.6418(11) _cell_length_b 12.7390(18) _cell_length_c 24.237(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2359.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1240 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 21.38 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 2.224 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8509 _exptl_absorpt_correction_T_max 0.9548 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11804 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 26.49 _reflns_number_total 2442 _reflns_number_gt 1725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0325P)^2^+1.9186P] 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 2442 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 0.21698(5) 0.44564(3) 0.034546(15) 0.01956(13) Uani 1 1 d . . . Cl1 Cl 0.11088(17) 0.50337(10) -0.06330(5) 0.0235(3) Uani 1 1 d . . . P1 P 0.44433(18) 0.67202(10) 0.04369(5) 0.0161(3) Uani 1 1 d . . . O1 O 0.3690(5) 0.7756(3) 0.02516(14) 0.0249(9) Uani 1 1 d . . . O2 O 0.3107(5) 0.6004(3) 0.07227(14) 0.0243(9) Uani 1 1 d . . . O3 O 0.5344(5) 0.6167(3) -0.00285(14) 0.0228(9) Uani 1 1 d . . . O4 O 0.77762(18) 1.05251(11) 0.33064(6) 0.0333(10) Uani 1 1 d . . . H4B H 0.7586 1.0731 0.3635 0.050 Uiso 1 1 d R . . O5 O 0.77308(18) 0.89461(11) 0.37073(6) 0.0252(9) Uani 1 1 d R . . N1 N 0.75498(18) 0.76161(11) 0.07958(6) 0.0188(10) Uani 1 1 d R . . H1B H 0.7211 0.8289 0.0757 0.023 Uiso 1 1 d R . . H1E H 0.7874 0.7383 0.0460 0.023 Uiso 1 1 d R . . C1 C 0.60183(18) 0.69899(11) 0.09827(6) 0.0221(13) Uani 1 1 d R . . H1C H 0.6428 0.6336 0.1131 0.027 Uiso 1 1 d R . . H1D H 0.5438 0.7362 0.1274 0.027 Uiso 1 1 d R . . C2 C 0.91212(18) 0.75869(11) 0.11694(6) 0.0241(13) Uani 1 1 d R . . H2A H 1.0075 0.7946 0.0994 0.029 Uiso 1 1 d R . . H2B H 0.9467 0.6870 0.1225 0.029 Uiso 1 1 d R . . C3 C 0.87706(18) 0.80867(11) 0.17211(6) 0.0193(12) Uani 1 1 d R . . C4 C 0.85372(18) 0.74799(11) 0.21905(6) 0.0286(14) Uani 1 1 d R . . H4A H 0.8583 0.6729 0.2163 0.034 Uiso 1 1 d R . . C8 C 0.87654(18) 0.91651(11) 0.17739(6) 0.0231(13) Uani 1 1 d R . . H8A H 0.8953 0.9594 0.1454 0.028 Uiso 1 1 d R . . C7 C 0.84942(18) 0.96402(11) 0.22820(6) 0.0256(13) Uani 1 1 d R . . H7A H 0.8495 1.0391 0.2312 0.031 Uiso 1 1 d R . . C5 C 0.82399(18) 0.79407(11) 0.26964(6) 0.0258(14) Uani 1 1 d R . . H5A H 0.8045 0.7510 0.3016 0.031 Uiso 1 1 d R . . C6 C 0.82219(18) 0.90233(11) 0.27449(6) 0.0208(12) Uani 1 1 d R . . C9 C 0.78884(18) 0.94984(11) 0.32980(6) 0.0233(12) Uani 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 Cd1 0.0211(2) 0.0177(2) 0.0199(2) -0.00126(17) 0.00022(18) 0.00118(18) Cl1 0.0213(7) 0.0257(7) 0.0236(7) 0.0011(6) 0.0007(6) 0.0018(6) P1 0.0169(7) 0.0149(7) 0.0165(7) -0.0003(5) -0.0001(6) -0.0013(6) O1 0.035(2) 0.0177(19) 0.022(2) 0.0000(16) -0.0065(18) 0.0083(18) O2 0.029(2) 0.024(2) 0.020(2) -0.0015(17) 0.0051(18) -0.0095(18) O3 0.020(2) 0.025(2) 0.023(2) -0.0047(17) 0.0009(17) 0.0035(17) O4 0.055(3) 0.025(2) 0.020(2) -0.0002(18) 0.004(2) 0.002(2) O5 0.035(2) 0.025(2) 0.0155(18) -0.0011(17) -0.0001(18) -0.0074(19) N1 0.028(3) 0.015(2) 0.013(2) -0.0031(18) -0.0053(19) -0.001(2) C1 0.025(3) 0.024(3) 0.018(3) 0.002(2) 0.005(2) -0.005(3) C2 0.019(3) 0.027(3) 0.026(3) -0.004(3) -0.001(2) -0.009(3) C3 0.017(3) 0.022(3) 0.019(3) -0.002(2) -0.002(2) -0.004(2) C4 0.036(3) 0.021(3) 0.029(3) -0.004(3) 0.001(3) -0.010(3) C8 0.031(3) 0.020(3) 0.019(3) 0.008(2) -0.004(3) 0.001(3) C7 0.031(3) 0.026(3) 0.020(3) 0.003(2) -0.001(3) 0.004(3) C5 0.034(4) 0.025(3) 0.018(3) 0.005(2) -0.001(3) -0.004(3) C6 0.014(3) 0.023(3) 0.026(3) -0.003(2) -0.003(2) -0.006(2) C9 0.021(3) 0.030(3) 0.019(3) 0.001(3) -0.002(2) -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 O3 2.197(3) 5_665 ? Cd1 O1 2.276(3) 8_655 ? Cd1 O2 2.288(4) . ? Cd1 O5 2.3874(14) 3_645 ? Cd1 Cl1 2.6118(14) . ? Cd1 Cl1 2.6804(14) 5_565 ? Cl1 Cd1 2.6804(14) 5_565 ? P1 O3 1.498(4) . ? P1 O1 1.507(4) . ? P1 O2 1.535(4) . ? P1 C1 1.8211(19) . ? O1 Cd1 2.276(3) 8_665 ? O3 Cd1 2.197(3) 5_665 ? O4 C9 1.3109 . ? O4 H4B 0.8500 . ? O5 C9 1.2221 . ? O5 Cd1 2.3874(14) 3_655 ? N1 C1 1.4870 . ? N1 C2 1.5044 . ? N1 H1B 0.9000 . ? N1 H1E 0.9001 . ? C1 H1C 0.9601 . ? C1 H1D 0.9600 . ? C2 C3 1.5050 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C3 C8 1.3797 . ? C3 C4 1.3870 . ? C4 C5 1.3783 . ? C4 H4A 0.9601 . ? C8 C7 1.3877 . ? C8 H8A 0.9601 . ? C7 C6 1.3855 . ? C7 H7A 0.9599 . ? C5 C6 1.3842 . ? C5 H5A 0.9600 . ? C6 C9 1.4927 . ? 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 O3 Cd1 O1 82.58(13) 5_665 8_655 ? O3 Cd1 O2 100.39(13) 5_665 . ? O1 Cd1 O2 161.94(12) 8_655 . ? O3 Cd1 O5 102.14(10) 5_665 3_645 ? O1 Cd1 O5 81.15(9) 8_655 3_645 ? O2 Cd1 O5 80.81(10) . 3_645 ? O3 Cd1 Cl1 93.02(10) 5_665 . ? O1 Cd1 Cl1 95.03(9) 8_655 . ? O2 Cd1 Cl1 102.56(10) . . ? O5 Cd1 Cl1 163.68(5) 3_645 . ? O3 Cd1 Cl1 170.56(10) 5_665 5_565 ? O1 Cd1 Cl1 89.24(10) 8_655 5_565 ? O2 Cd1 Cl1 88.84(10) . 5_565 ? O5 Cd1 Cl1 81.13(5) 3_645 5_565 ? Cl1 Cd1 Cl1 82.97(4) . 5_565 ? Cd1 Cl1 Cd1 97.03(4) . 5_565 ? O3 P1 O1 111.3(2) . . ? O3 P1 O2 111.5(2) . . ? O1 P1 O2 113.6(2) . . ? O3 P1 C1 109.39(16) . . ? O1 P1 C1 107.67(16) . . ? O2 P1 C1 102.95(16) . . ? P1 O1 Cd1 156.0(2) . 8_665 ? P1 O2 Cd1 122.7(2) . . ? P1 O3 Cd1 146.2(2) . 5_665 ? C9 O4 H4B 109.5 . . ? C9 O5 Cd1 128.4 . 3_655 ? C1 N1 C2 115.6 . . ? C1 N1 H1B 108.4 . . ? C2 N1 H1B 108.4 . . ? C1 N1 H1E 108.4 . . ? C2 N1 H1E 108.4 . . ? H1B N1 H1E 107.4 . . ? N1 C1 P1 113.58(6) . . ? N1 C1 H1C 108.8 . . ? P1 C1 H1C 108.9 . . ? N1 C1 H1D 108.8 . . ? P1 C1 H1D 108.8 . . ? H1C C1 H1D 107.7 . . ? N1 C2 C3 112.5 . . ? N1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C8 C3 C4 118.6 . . ? C8 C3 C2 120.3 . . ? C4 C3 C2 121.1 . . ? C5 C4 C3 120.9 . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.5 . . ? C3 C8 C7 121.1 . . ? C3 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? C6 C7 C8 119.6 . . ? C6 C7 H7A 120.2 . . ? C8 C7 H7A 120.2 . . ? C4 C5 C6 120.1 . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 120.0 . . ? C5 C6 C7 119.7 . . ? C5 C6 C9 118.8 . . ? C7 C6 C9 121.5 . . ? O5 C9 O4 123.7 . . ? O5 C9 C6 120.8 . . ? O4 C9 C6 115.4 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.569 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.147