# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Gagnon, Kevin' 'Prosvirin, Andrey V.' 'Dunbar, K.' 'Teat, Simon' 'Clearfield, Abraham' _publ_contact_author_name 'Gagnon, Kevin' _publ_contact_author_email kgagnon@mail.chem.tamu.edu _publ_section_title ; Hydro-ionothermal syntheses, crystal structures, and properties of five new divalent metal iminophosphonates ; # Attachment '- 1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 848512' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H16 Co N2 O12 P4' _chemical_formula_sum 'C4 H16 Co N2 O12 P4' _chemical_formula_weight 467.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.3609(3) _cell_length_b 8.5315(3) _cell_length_c 9.3542(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.530(2) _cell_angle_gamma 90.00 _cell_volume 742.20(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8397 _cell_measurement_theta_min 2.387 _cell_measurement_theta_max 28.2855 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.090 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474 _exptl_absorpt_coefficient_mu 1.653 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8655 _exptl_absorpt_correction_T_max 0.9368 _exptl_absorpt_process_details 'SADABS 2008/1 Bruker AXS Madison WI USA' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _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 8184 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1386 _reflns_number_gt 1378 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.60a' _computing_data_reduction 'Bruker SAINT v7.60a' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _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. All hydrogens were refined anisotropically. Hydrogens were placed geometrically on the carbon atoms and refined using a riding model. The hydroxyl and amine hydrogen atoms were found in the difference map, their distance to their O or N were restrained but the coordinates were allowed to refine, but the displacement parameters were ridden on their N or O. ; _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^)+(0.0326P)^2^+0.8776P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1386 _refine_ls_number_parameters 130 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0616 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 Co1 Co 0.5000 0.0000 1.0000 0.00655(12) Uani 1 2 d S . . P1 P 0.82923(5) 0.15924(5) 1.03780(5) 0.00780(14) Uani 1 1 d . . . P2 P 0.41527(5) 0.18608(5) 1.28466(5) 0.00686(14) Uani 1 1 d . . . O2 O 0.87811(14) 0.10933(16) 0.89622(14) 0.0103(3) Uani 1 1 d . . . O1 O 0.67498(14) 0.13809(15) 1.06039(15) 0.0104(3) Uani 1 1 d . . . O6 O 0.54814(14) 0.09059(15) 1.36032(14) 0.0101(3) Uani 1 1 d D . . O4 O 0.38396(14) 0.14041(15) 1.12966(14) 0.0093(3) Uani 1 1 d . . . O5 O 0.43517(14) 0.14152(15) 0.81537(14) 0.0100(3) Uani 1 1 d . . . N1 N 0.25655(18) -0.05596(19) 1.36887(18) 0.0082(3) Uani 1 1 d . . . O3 O 0.93035(15) 0.08575(17) 1.16595(14) 0.0136(3) Uani 1 1 d D . . C2 C 0.2675(2) 0.1186(2) 1.3795(2) 0.0092(4) Uani 1 1 d . . . C1 C 0.8555(2) 0.3719(2) 1.0504(2) 0.0101(4) Uani 1 1 d . . . H2A H 0.176(3) 0.161(3) 1.337(3) 0.012 Uiso 1 1 d . . . H2B H 0.285(3) 0.148(3) 1.477(3) 0.012 Uiso 1 1 d . . . H3A H 0.239(3) -0.080(3) 1.284(3) 0.012 Uiso 1 1 d . . . H1B H 0.945(3) 0.404(3) 1.098(3) 0.012 Uiso 1 1 d . . . H1A H 0.841(2) 0.419(3) 0.951(3) 0.012 Uiso 1 1 d . . . H3B H 0.336(3) -0.096(3) 1.402(3) 0.012 Uiso 1 1 d . . . H3 H 0.990(2) 0.020(2) 1.141(3) 0.012 Uiso 1 1 d D . . H6 H 0.563(3) 0.0094(19) 1.313(2) 0.012 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0078(2) 0.00542(19) 0.0065(2) -0.00028(12) 0.00121(14) -0.00014(12) P1 0.0082(3) 0.0072(2) 0.0079(3) -0.00081(17) 0.00082(18) 0.00107(17) P2 0.0085(2) 0.0054(2) 0.0067(2) -0.00013(17) 0.00109(18) -0.00041(17) O2 0.0110(6) 0.0110(7) 0.0089(7) -0.0008(5) 0.0013(5) 0.0027(5) O1 0.0089(6) 0.0089(6) 0.0138(7) -0.0014(5) 0.0025(5) -0.0011(5) O6 0.0123(7) 0.0085(6) 0.0091(6) -0.0017(5) -0.0007(5) 0.0023(5) O4 0.0106(6) 0.0091(6) 0.0081(7) -0.0004(5) 0.0008(5) 0.0012(5) O5 0.0146(7) 0.0066(6) 0.0087(7) 0.0004(5) 0.0014(5) 0.0008(5) N1 0.0093(8) 0.0074(8) 0.0080(8) 0.0003(6) 0.0008(6) 0.0001(6) O3 0.0153(7) 0.0160(7) 0.0092(7) -0.0009(5) 0.0003(5) 0.0081(6) C2 0.0120(9) 0.0068(9) 0.0090(9) -0.0009(7) 0.0023(7) -0.0006(7) C1 0.0088(9) 0.0098(9) 0.0122(9) -0.0017(7) 0.0037(7) -0.0004(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.0444(13) . ? Co1 O1 2.0444(13) 3_657 ? Co1 O4 2.0942(13) 3_657 ? Co1 O4 2.0942(13) . ? Co1 O5 2.1378(13) 3_657 ? Co1 O5 2.1378(13) . ? P1 O1 1.4938(14) . ? P1 O2 1.5107(14) . ? P1 O3 1.5710(14) . ? P1 C1 1.833(2) . ? P2 O4 1.4977(14) . ? P2 O5 1.5061(13) 4_566 ? P2 O6 1.5847(13) . ? P2 C2 1.820(2) . ? O6 H6 0.840(10) . ? N1 C1 1.493(2) 2_647 ? N1 C2 1.495(2) . ? N1 H3A 0.82(3) . ? N1 H3B 0.84(3) . ? O3 H3 0.839(10) . ? C2 H2A 0.97(3) . ? C2 H2B 0.94(2) . ? C1 H1B 0.94(3) . ? C1 H1A 1.01(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 180.0 . 3_657 ? O1 Co1 O4 92.16(5) . 3_657 ? O1 Co1 O4 87.84(5) 3_657 3_657 ? O1 Co1 O4 87.84(5) . . ? O1 Co1 O4 92.16(5) 3_657 . ? O4 Co1 O4 180.000(1) 3_657 . ? O1 Co1 O5 87.55(5) . 3_657 ? O1 Co1 O5 92.45(5) 3_657 3_657 ? O4 Co1 O5 91.52(5) 3_657 3_657 ? O4 Co1 O5 88.48(5) . 3_657 ? O1 Co1 O5 92.45(5) . . ? O1 Co1 O5 87.55(5) 3_657 . ? O4 Co1 O5 88.48(5) 3_657 . ? O4 Co1 O5 91.52(5) . . ? O5 Co1 O5 180.0 3_657 . ? O1 P1 O2 118.94(8) . . ? O1 P1 O3 110.62(8) . . ? O2 P1 O3 109.89(8) . . ? O1 P1 C1 103.60(8) . . ? O2 P1 C1 106.47(8) . . ? O3 P1 C1 106.34(9) . . ? O4 P2 O5 116.43(8) . 4_566 ? O4 P2 O6 110.85(7) . . ? O5 P2 O6 110.07(8) 4_566 . ? O4 P2 C2 108.28(8) . . ? O5 P2 C2 107.48(8) 4_566 . ? O6 P2 C2 102.78(8) . . ? P1 O1 Co1 141.95(9) . . ? P2 O6 H6 110.8(18) . . ? P2 O4 Co1 130.71(8) . . ? P2 O5 Co1 136.32(8) 4_565 . ? C1 N1 C2 115.07(15) 2_647 . ? C1 N1 H3A 108.3(17) 2_647 . ? C2 N1 H3A 108.4(18) . . ? C1 N1 H3B 106.5(17) 2_647 . ? C2 N1 H3B 109.5(17) . . ? H3A N1 H3B 109(2) . . ? P1 O3 H3 114.7(18) . . ? N1 C2 P2 109.44(13) . . ? N1 C2 H2A 107.1(14) . . ? P2 C2 H2A 111.5(14) . . ? N1 C2 H2B 109.2(15) . . ? P2 C2 H2B 109.3(15) . . ? H2A C2 H2B 110(2) . . ? N1 C1 P1 110.12(13) 2_657 . ? N1 C1 H1B 105.9(14) 2_657 . ? P1 C1 H1B 115.1(15) . . ? N1 C1 H1A 106.0(14) 2_657 . ? P1 C1 H1A 109.5(14) . . ? H1B C1 H1A 109.8(19) . . ? 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 H3A O2 0.82(3) 1.92(3) 2.690(2) 156(2) 3_657 N1 H3B O1 0.84(3) 2.30(3) 2.751(2) 114(2) 2_647 N1 H3B O6 0.84(3) 2.36(3) 2.965(2) 129(2) 3_658 N1 H3B O6 0.84(3) 2.61(2) 3.012(2) 110(2) . O3 H3 O2 0.839(10) 1.724(10) 2.5613(19) 175(3) 3_757 O6 H6 O5 0.840(10) 1.764(11) 2.5894(18) 167(3) 3_657 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.329 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.092 # Attachment '- 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 848513' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H20 Co N2 O14 P4' _chemical_formula_sum 'C4 H20 Co N2 O14 P4' _chemical_formula_weight 503.03 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.6188(16) _cell_length_b 6.049(2) _cell_length_c 13.927(5) _cell_angle_alpha 87.525(4) _cell_angle_beta 85.217(4) _cell_angle_gamma 84.475(4) _cell_volume 385.7(2) _cell_formula_units_Z 1 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2220 _cell_measurement_theta_min 2.937 _cell_measurement_theta_max 28.258 _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 257 _exptl_absorpt_coefficient_mu 1.608 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6921 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3668 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1363 _reflns_number_gt 1212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.60a' _computing_data_reduction 'Bruker SAINT v7.60a' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _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. All hydrogens were refined anisotropically. Hydrgeons were placed geometrically on the carbon atoms and refined using a riding model. The hydroxyl and amine hydrogen atoms were found in the difference map, their distance to their O or N were restrained but the coordinates were allowed to refine, but the dispalcement parameters were ridden on their N or O. ; _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^)+(0.0573P)^2^+0.0214P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1363 _refine_ls_number_parameters 115 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 O2 O -0.3327(4) 1.2221(3) 0.55523(13) 0.0099(4) Uani 1 1 d . . . Co1 Co -1.0000 1.0000 0.5000 0.00730(19) Uani 1 2 d S . . P2 P 0.11749(15) 0.66385(11) 0.87231(5) 0.0082(2) Uani 1 1 d . . . P1 P -0.57225(15) 1.20800(11) 0.63449(5) 0.0073(2) Uani 1 1 d . . . O1 O -0.7783(4) 1.0329(3) 0.62329(13) 0.0094(4) Uani 1 1 d . . . O4 O -0.0464(4) 0.4595(3) 0.88174(13) 0.0108(4) Uani 1 1 d . . . O5 O 0.3299(4) 0.6688(3) 0.78361(13) 0.0093(4) Uani 1 1 d . . . O1W O -0.7999(4) 1.2691(3) 0.42186(13) 0.0106(4) Uani 1 1 d . . . H1WA H -0.9272 1.3754 0.4132 0.016 Uiso 1 1 calc R . . H1WB H -0.6675 1.3190 0.4354 0.016 Uiso 1 1 d R . . O3 O -0.7504(4) 1.4398(3) 0.64528(14) 0.0111(4) Uani 1 1 d D . . H3 H -0.7299 1.4888 0.6996 0.013 Uiso 1 1 calc RD . . O6 O 0.2731(4) 0.7037(3) 0.96357(13) 0.0107(4) Uani 1 1 d . . . H6 H 0.1795 0.6525 1.0125 0.013 Uiso 1 1 calc R . . N1 N -0.2391(5) 0.9473(4) 0.76296(16) 0.0083(5) Uani 1 1 d . . . H1A H -0.0818 0.9415 0.7178 0.010 Uiso 1 1 calc R . . H1B H -0.3495 0.8336 0.7519 0.010 Uiso 1 1 calc R . . C2 C -0.1317(6) 0.9139(4) 0.86155(19) 0.0086(6) Uani 1 1 d . . . H2A H -0.3007 0.9040 0.9097 0.010 Uiso 1 1 calc R . . H2B H -0.0310 1.0443 0.8762 0.010 Uiso 1 1 calc R . . C1 C -0.4178(6) 1.1635(4) 0.7511(2) 0.0091(6) Uani 1 1 d . . . H1C H -0.2947 1.2852 0.7600 0.011 Uiso 1 1 calc R . . H1D H -0.5794 1.1725 0.8026 0.011 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 O2 0.0090(10) 0.0115(10) 0.0087(10) 0.0034(8) 0.0026(8) -0.0034(8) Co1 0.0059(3) 0.0091(3) 0.0069(3) 0.0030(2) 0.0006(2) -0.0034(2) P2 0.0081(4) 0.0095(4) 0.0072(4) 0.0035(3) 0.0003(3) -0.0038(3) P1 0.0063(4) 0.0088(4) 0.0069(4) 0.0028(3) 0.0001(3) -0.0030(3) O1 0.0078(10) 0.0113(10) 0.0094(10) 0.0027(8) 0.0003(8) -0.0051(8) O4 0.0130(10) 0.0100(10) 0.0099(10) 0.0024(8) 0.0000(8) -0.0062(8) O5 0.0083(10) 0.0118(10) 0.0082(10) 0.0025(8) 0.0012(8) -0.0052(8) O1W 0.0065(10) 0.0114(10) 0.0142(10) 0.0039(8) -0.0018(8) -0.0039(8) O3 0.0112(10) 0.0143(10) 0.0078(10) -0.0006(8) -0.0021(8) -0.0004(8) O6 0.0098(10) 0.0136(10) 0.0089(10) 0.0044(8) 0.0012(8) -0.0062(8) N1 0.0085(12) 0.0098(12) 0.0068(12) 0.0024(9) 0.0004(9) -0.0032(9) C2 0.0089(14) 0.0111(13) 0.0059(14) 0.0030(10) -0.0010(11) -0.0029(11) C1 0.0085(14) 0.0089(14) 0.0100(14) 0.0018(11) -0.0003(11) -0.0023(11) _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 O2 P1 1.502(2) . ? O2 Co1 2.0621(19) 1_655 ? Co1 O2 2.0621(19) 2_476 ? Co1 O2 2.0621(19) 1_455 ? Co1 O1 2.0972(19) 2_376 ? Co1 O1 2.0972(19) . ? Co1 O1W 2.1580(19) . ? Co1 O1W 2.1580(19) 2_376 ? P2 O4 1.506(2) . ? P2 O5 1.513(2) . ? P2 O6 1.550(2) . ? P2 C2 1.819(3) . ? P1 O1 1.512(2) . ? P1 O3 1.563(2) . ? P1 C1 1.827(3) . ? O1W H1WA 0.8400 . ? O1W H1WB 0.7488 . ? O3 H3 0.8400 . ? O6 H6 0.8400 . ? N1 C1 1.489(3) . ? N1 C2 1.498(3) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C1 H1C 0.9900 . ? C1 H1D 0.9900 . ? 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 P1 O2 Co1 134.03(11) . 1_655 ? O2 Co1 O2 180.000(1) 2_476 1_455 ? O2 Co1 O1 89.08(8) 2_476 2_376 ? O2 Co1 O1 90.92(8) 1_455 2_376 ? O2 Co1 O1 90.92(8) 2_476 . ? O2 Co1 O1 89.08(8) 1_455 . ? O1 Co1 O1 180.000(1) 2_376 . ? O2 Co1 O1W 89.98(8) 2_476 . ? O2 Co1 O1W 90.02(7) 1_455 . ? O1 Co1 O1W 86.58(7) 2_376 . ? O1 Co1 O1W 93.42(7) . . ? O2 Co1 O1W 90.02(7) 2_476 2_376 ? O2 Co1 O1W 89.98(8) 1_455 2_376 ? O1 Co1 O1W 93.42(7) 2_376 2_376 ? O1 Co1 O1W 86.58(7) . 2_376 ? O1W Co1 O1W 180.000(1) . 2_376 ? O4 P2 O5 113.42(11) . . ? O4 P2 O6 113.13(10) . . ? O5 P2 O6 110.31(11) . . ? O4 P2 C2 110.92(12) . . ? O5 P2 C2 105.46(12) . . ? O6 P2 C2 102.81(11) . . ? O2 P1 O1 115.25(11) . . ? O2 P1 O3 109.68(11) . . ? O1 P1 O3 109.48(11) . . ? O2 P1 C1 110.18(12) . . ? O1 P1 C1 109.15(12) . . ? O3 P1 C1 102.30(11) . . ? P1 O1 Co1 124.71(11) . . ? Co1 O1W H1WA 109.5 . . ? Co1 O1W H1WB 125.2 . . ? H1WA O1W H1WB 106.5 . . ? P1 O3 H3 109.5 . . ? P2 O6 H6 109.5 . . ? C1 N1 C2 112.2(2) . . ? C1 N1 H1A 109.2 . . ? C2 N1 H1A 109.2 . . ? C1 N1 H1B 109.2 . . ? C2 N1 H1B 109.2 . . ? H1A N1 H1B 107.9 . . ? N1 C2 P2 112.33(18) . . ? N1 C2 H2A 109.1 . . ? P2 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? P2 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? N1 C1 P1 114.43(18) . . ? N1 C1 H1C 108.7 . . ? P1 C1 H1C 108.7 . . ? N1 C1 H1D 108.7 . . ? P1 C1 H1D 108.7 . . ? H1C C1 H1D 107.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O3 0.84 1.98 2.787(3) 159.7 2_386 O1W H1WB O2 0.75 2.39 2.948(3) 133.1 . O3 H3 O5 0.84 1.69 2.493(3) 159.5 1_465 O6 H6 O4 0.84 1.69 2.520(3) 170.4 2_567 N1 H1A O1 0.92 1.94 2.831(3) 161.4 1_655 N1 H1B O5 0.92 1.88 2.719(3) 151.3 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.666 _refine_diff_density_min -0.796 _refine_diff_density_rms 0.103 # Attachment '- 3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 848514' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H20 Co N2 O12 P4' _chemical_formula_weight 495.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' P P 0.1013 0.1134 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Co Co 0.1761 1.1404 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 2(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 9.411(4) _cell_length_b 8.711(4) _cell_length_c 9.859(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.209(7) _cell_angle_gamma 90.00 _cell_volume 807.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3748 _cell_measurement_theta_min 3.405 _cell_measurement_theta_max 34.0385 _exptl_crystal_description plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.037 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 1.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.65 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details 'SADABS 2008/1 Bruker AXS Madison WI USA' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 7649 _diffrn_reflns_av_R_equivalents 0.0684 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1430 _reflns_number_gt 1327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.60a' _computing_data_reduction 'Bruker SAINT v7.60a' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _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. All hydrogens were refined anisotropically. Hydrgeons were placed geometrically on the carbon atoms and refined using a riding model. The hydroxyl and amine hydrogen atoms were found in the difference map, their distance to their O or N were restrained but the coordinates were allowed to refine, but the dispalcement parameters were ridden on their N or O. ; _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^)+(0.0224P)^2^+1.3202P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 1430 _refine_ls_number_parameters 124 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.0000 0.0000 0.00773(18) Uani 1 2 d S . . P1 P 0.44111(8) 0.29676(8) -0.21250(7) 0.0089(2) Uani 1 1 d . . . P2 P 0.83020(8) 0.11594(8) -0.07727(7) 0.0093(2) Uani 1 1 d . . . O3 O 0.3056(2) 0.3812(2) -0.16175(19) 0.0129(4) Uani 1 1 d D . . O1 O 0.4424(2) 0.1316(2) -0.16719(18) 0.0110(4) Uani 1 1 d . . . O4 O 0.7102(2) 0.0919(2) 0.01472(19) 0.0111(4) Uani 1 1 d . . . O2 O 0.4562(2) 0.1818(2) 0.13777(19) 0.0105(4) Uani 1 1 d . . . N1 N 0.7206(3) 0.3986(3) -0.1923(2) 0.0111(5) Uani 1 1 d D . . C1 C 0.5858(3) 0.3982(3) -0.1171(3) 0.0104(6) Uani 1 1 d . . . H1A H 0.5563 0.5054 -0.1007 0.012 Uiso 1 1 calc R . . H1B H 0.6041 0.3480 -0.0277 0.012 Uiso 1 1 calc R . . C2 C 0.7790(3) 0.2408(3) -0.2191(3) 0.0114(6) Uani 1 1 d . . . H2A H 0.8636 0.2541 -0.2733 0.014 Uiso 1 1 calc R . . H2B H 0.7067 0.1855 -0.2773 0.014 Uiso 1 1 calc R . . C3 C 0.8289(3) 0.5057(3) -0.1262(3) 0.0143(6) Uani 1 1 d . . . H3A H 0.9156 0.5038 -0.1767 0.021 Uiso 1 1 calc R . . H3B H 0.8513 0.4729 -0.0324 0.021 Uiso 1 1 calc R . . H3C H 0.7903 0.6102 -0.1265 0.021 Uiso 1 1 calc R . . O5 O 0.9568(2) 0.2040(2) -0.0020(2) 0.0134(4) Uani 1 1 d D . . O6 O 0.8828(2) -0.0269(2) -0.1476(2) 0.0121(4) Uani 1 1 d . . . H1N1 H 0.698(4) 0.440(4) -0.2815(18) 0.018 Uiso 1 1 d D . . H4A H 0.245(3) 0.392(4) -0.229(2) 0.018 Uiso 1 1 d D . . H5A H 1.009(3) 0.145(3) 0.057(3) 0.018 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0149(3) 0.0020(3) 0.0063(3) 0.00057(18) 0.0011(2) -0.0001(2) P1 0.0153(4) 0.0028(4) 0.0086(4) 0.0005(3) 0.0011(3) 0.0001(3) P2 0.0145(4) 0.0045(4) 0.0089(4) 0.0007(3) 0.0006(3) 0.0006(3) O3 0.0163(11) 0.0123(11) 0.0100(10) -0.0008(8) 0.0005(8) 0.0047(8) O1 0.0200(11) 0.0033(10) 0.0097(9) 0.0016(7) 0.0005(8) -0.0019(8) O4 0.0173(11) 0.0067(9) 0.0093(9) -0.0002(7) 0.0011(8) -0.0016(8) O2 0.0160(11) 0.0064(10) 0.0093(9) -0.0004(7) 0.0013(8) 0.0007(8) N1 0.0171(13) 0.0066(12) 0.0095(11) -0.0002(9) 0.0012(10) 0.0004(10) C1 0.0151(15) 0.0065(13) 0.0099(13) -0.0021(11) 0.0026(11) 0.0007(11) C2 0.0156(15) 0.0097(14) 0.0089(13) -0.0001(11) 0.0013(11) 0.0026(11) C3 0.0173(16) 0.0085(14) 0.0169(15) -0.0003(11) -0.0001(12) -0.0020(11) O5 0.0177(11) 0.0082(10) 0.0138(10) 0.0001(8) -0.0023(8) 0.0000(8) O6 0.0171(11) 0.0070(10) 0.0122(10) -0.0019(8) 0.0005(8) 0.0020(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.0555(19) 3_655 ? Co1 O1 2.0555(19) . ? Co1 O4 2.132(2) 3_655 ? Co1 O4 2.132(2) . ? Co1 O2 2.141(2) . ? Co1 O2 2.141(2) 3_655 ? P1 O2 1.503(2) 4_565 ? P1 O1 1.506(2) . ? P1 O3 1.577(2) . ? P1 C1 1.838(3) . ? P2 O4 1.502(2) . ? P2 O6 1.521(2) . ? P2 O5 1.568(2) . ? P2 C2 1.815(3) . ? O3 H4A 0.856(10) . ? O2 P1 1.503(2) 4_566 ? N1 C3 1.503(4) . ? N1 C1 1.505(4) . ? N1 C2 1.509(4) . ? N1 H1N1 0.964(10) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? O5 H5A 0.896(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 180.00(10) 3_655 . ? O1 Co1 O4 92.71(8) 3_655 3_655 ? O1 Co1 O4 87.29(8) . 3_655 ? O1 Co1 O4 87.29(8) 3_655 . ? O1 Co1 O4 92.71(8) . . ? O4 Co1 O4 180.00(10) 3_655 . ? O1 Co1 O2 87.43(8) 3_655 . ? O1 Co1 O2 92.57(8) . . ? O4 Co1 O2 96.33(8) 3_655 . ? O4 Co1 O2 83.67(8) . . ? O1 Co1 O2 92.57(8) 3_655 3_655 ? O1 Co1 O2 87.43(8) . 3_655 ? O4 Co1 O2 83.67(8) 3_655 3_655 ? O4 Co1 O2 96.33(8) . 3_655 ? O2 Co1 O2 180.00(8) . 3_655 ? O2 P1 O1 114.24(11) 4_565 . ? O2 P1 O3 112.10(11) 4_565 . ? O1 P1 O3 110.15(11) . . ? O2 P1 C1 109.56(12) 4_565 . ? O1 P1 C1 108.31(12) . . ? O3 P1 C1 101.69(12) . . ? O4 P2 O6 115.88(12) . . ? O4 P2 O5 111.05(12) . . ? O6 P2 O5 110.98(12) . . ? O4 P2 C2 111.86(13) . . ? O6 P2 C2 102.59(12) . . ? O5 P2 C2 103.49(13) . . ? P1 O3 H4A 109(2) . . ? P1 O1 Co1 140.15(12) . . ? P2 O4 Co1 137.51(12) . . ? P1 O2 Co1 138.37(12) 4_566 . ? C3 N1 C1 110.9(2) . . ? C3 N1 C2 113.4(2) . . ? C1 N1 C2 114.2(2) . . ? C3 N1 H1N1 106(2) . . ? C1 N1 H1N1 107(2) . . ? C2 N1 H1N1 104(2) . . ? N1 C1 P1 111.70(18) . . ? N1 C1 H1A 109.3 . . ? P1 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? P1 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? N1 C2 P2 119.63(19) . . ? N1 C2 H2A 107.4 . . ? P2 C2 H2A 107.4 . . ? N1 C2 H2B 107.4 . . ? P2 C2 H2B 107.4 . . ? H2A C2 H2B 106.9 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? P2 O5 H5A 114(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 O5 H5A O6 0.896(10) 1.676(12) 2.566(3) 172(3) 3_755 O3 H4A O6 0.856(10) 1.805(14) 2.635(3) 163(3) 2_654 N1 H1N1 O1 0.964(10) 2.17(3) 2.855(3) 127(3) 2_654 N1 H1N1 O4 0.964(10) 2.04(2) 2.886(3) 146(3) 4_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.460 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.093 # Attachment '- 4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 848515' #TrackingRef '- 4.cif' _chemical_formula_moiety 'C4 N2 O12 P4 Zn3' _chemical_formula_sum 'C4 N2 O12 P4 Zn3' _chemical_formula_weight 600.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system Orthorhombic _space_group_name_H-M_alt P21212 loop_ _symmetry_equiv_pos_as_xyz '-x, -y, z' '-x+1/2, y+1/2, -z' 'x, y, z' 'x+1/2, -y+1/2, -z' _cell_length_a 10.6881(3) _cell_length_b 13.3129(3) _cell_length_c 5.4266(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 772.14 _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _exptl_crystal_density_diffrn 2.58 _diffrn_ambient_temperature 298(2) _diffrn_source 'sealed X-ray tube' _diffrn_radiation_probe X-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54175 _pd_meas_2theta_range_min 8 _pd_meas_2theta_range_max 57 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z Zn1 Zn 0.31969 0.12269 0.50986 Zn2 Zn 0 0 0.31303 P1 P 0.22809 0.50439 0.98344 P2 P 0.04918 0.21796 0.56927 O1 O 0.3642 0.5224 0.9172 O2 O 0.1409 0.5602 0.8191 O3 O 0.1994 0.5193 1.2517 O4 O -0.0248 0.1213 0.5109 C1 C 0.0413 0.2387 0.8915 O6 O -0.019 0.3083 0.4454 N1 N 0.0736 0.3426 0.9784 O5 O 0.1806 0.2161 0.4757 C2 C 0.2059 0.3721 0.9323 #END # Attachment '- 5.cif' data_t1 _database_code_depnum_ccdc_archive 'CCDC 848516' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H7 Cl Cu N O3 P' _chemical_formula_weight 223.05 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 14.354(7) _cell_length_b 6.278(2) _cell_length_c 7.706(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.927(7) _cell_angle_gamma 90.00 _cell_volume 639.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2987 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 29.247 _exptl_crystal_description blade _exptl_crystal_colour blue-green _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 4.011 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6036 _exptl_absorpt_correction_T_max 0.9610 _exptl_absorpt_process_details 'SADABS 2008/1 Bruker AXS Madison WI USA' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3741 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.48 _reflns_number_total 800 _reflns_number_gt 777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.60a' _computing_data_reduction 'Bruker SAINT v7.60a' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _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. All hydrogens were refined anisotropically. Hydrgeons were placed geometrically on the carbon atoms and refined using a riding model. The amine hydrogen atoms were found in the difference map, their distance to their N were restrained but the coordinates were allowed to refine, but the dispalcement parameters were ridden on their N. ; _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^)+(0.0232P)^2^+1.3393P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 800 _refine_ls_number_parameters 58 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0177 _refine_ls_R_factor_gt 0.0171 _refine_ls_wR_factor_ref 0.0483 _refine_ls_wR_factor_gt 0.0477 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 Cu1 Cu 0.09967(2) 0.0000 0.91917(4) 0.01014(10) Uani 1 2 d S . . Cl2 Cl -0.07391(4) 0.0000 0.74031(9) 0.01517(14) Uani 1 2 d S . . P1 P 0.34079(4) 0.0000 1.03227(8) 0.00902(14) Uani 1 2 d S . . O1 O 0.24418(12) 0.0000 1.0661(2) 0.0129(3) Uani 1 2 d S . . C1 C 0.30504(19) 0.0000 0.7794(4) 0.0188(5) Uani 1 2 d S . . O2 O 0.09242(8) 0.3054(2) 0.89016(17) 0.0148(3) Uani 1 1 d . . . N1 N 0.39415(16) 0.0000 0.7270(3) 0.0127(4) Uani 1 2 d S . . C2 C 0.3676(2) 0.0000 0.5194(4) 0.0199(5) Uani 1 2 d S . . H2A H 0.2939 0.0000 0.4529 0.024 Uiso 1 2 calc SR . . H2B H 0.3958 -0.1275 0.4846 0.024 Uiso 0.50 1 calc PR . . H2C H 0.3958 0.1275 0.4846 0.024 Uiso 0.50 1 calc PR . . H1A H 0.2672(18) 0.129(4) 0.725(3) 0.024 Uiso 1 1 d . . . H1C H 0.4296(17) 0.105(4) 0.773(3) 0.024 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00858(16) 0.00403(16) 0.01764(17) 0.000 0.00493(12) 0.000 Cl2 0.0112(3) 0.0081(3) 0.0234(3) 0.000 0.0037(2) 0.000 P1 0.0080(3) 0.0053(3) 0.0135(3) 0.000 0.0040(2) 0.000 O1 0.0095(7) 0.0124(8) 0.0175(8) 0.000 0.0059(6) 0.000 C1 0.0110(11) 0.0285(15) 0.0157(12) 0.000 0.0041(9) 0.000 O2 0.0109(5) 0.0059(6) 0.0247(6) 0.0007(5) 0.0039(5) -0.0014(4) N1 0.0122(9) 0.0100(10) 0.0149(10) 0.000 0.0039(8) 0.000 C2 0.0236(13) 0.0216(14) 0.0157(12) 0.000 0.0090(10) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.9283(15) 6 ? Cu1 O2 1.9283(15) . ? Cu1 O1 1.9377(19) . ? Cu1 Cl2 2.3308(11) . ? P1 O1 1.5074(18) . ? P1 O2 1.5240(13) 7_557 ? P1 O2 1.5240(13) 4_547 ? P1 C1 1.812(3) . ? C1 N1 1.484(3) . ? C1 H1A 0.97(2) . ? O2 P1 1.5240(13) 7_557 ? N1 C2 1.493(3) . ? N1 H1C 0.82(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? 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 O2 Cu1 O2 167.70(8) 6 . ? O2 Cu1 O1 93.72(3) 6 . ? O2 Cu1 O1 93.72(3) . . ? O2 Cu1 Cl2 86.24(3) 6 . ? O2 Cu1 Cl2 86.24(3) . . ? O1 Cu1 Cl2 179.55(5) . . ? O1 P1 O2 114.38(6) . 7_557 ? O1 P1 O2 114.38(6) . 4_547 ? O2 P1 O2 106.57(10) 7_557 4_547 ? O1 P1 C1 106.96(11) . . ? O2 P1 C1 107.05(7) 7_557 . ? O2 P1 C1 107.05(7) 4_547 . ? P1 O1 Cu1 138.29(11) . . ? N1 C1 P1 112.31(17) . . ? N1 C1 H1A 106.4(14) . . ? P1 C1 H1A 109.6(14) . . ? P1 O2 Cu1 138.96(8) 7_557 . ? C2 N1 C1 113.9(2) . . ? C2 N1 H1C 108.3(16) . . ? C1 N1 H1C 109.8(16) . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 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 N1 H1C O2 0.82(2) 2.22(2) 2.896(2) 139(2) 8 N1 H1C Cl2 0.82(2) 2.49(2) 3.1680(12) 140(2) 3 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.462 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.077