# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H7 N O4 P Zn' _chemical_formula_weight 241.48 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 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 11.4350(7) _cell_length_b 5.2040(2) _cell_length_c 16.4787(10) _cell_angle_alpha 90.00 _cell_angle_beta 124.283(4) _cell_angle_gamma 90.00 _cell_volume 810.24(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1428 _cell_measurement_theta_min 3.61 _cell_measurement_theta_max 25.00 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.979 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 3.200 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.350 _exptl_absorpt_correction_T_max 0.395 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2724 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_unetl/netI 0.0568 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1428 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction,2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^)+(0.0664P)^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 0.034(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1424 _refine_ls_number_parameters 113 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 Zn1 Zn 0.33080(6) 0.27991(10) 0.89478(3) 0.0272(3) Uani 1 1 d . . . P1 P 0.66266(13) 0.2061(2) 1.00075(8) 0.0258(4) Uani 1 1 d . . . H1P H 0.736(5) 0.310(8) 0.969(3) 0.031 Uiso 1 1 d . . . O1 O 0.5104(4) 0.2033(7) 0.9154(3) 0.0465(10) Uani 1 1 d . . . O2 O 0.7216(4) -0.0625(6) 1.0359(2) 0.0369(8) Uani 1 1 d . . . O3 O 0.6924(4) 0.3671(6) 1.0857(2) 0.0532(12) Uani 1 1 d . . . N1 N 0.1939(4) 0.1978(7) 0.7486(3) 0.0266(9) Uani 1 1 d . . . C1 C 0.2089(6) 0.3157(10) 0.6839(3) 0.0390(13) Uani 1 1 d . . . H1 H 0.2717 0.4530 0.7050 0.047 Uiso 1 1 calc R . . C2 C 0.1355(7) 0.2440(8) 0.5863(4) 0.0363(14) Uani 1 1 d . . . H2 H 0.1500 0.3310 0.5434 0.044 Uiso 1 1 calc R . . C3 C 0.0402(4) 0.0421(7) 0.5526(3) 0.0237(10) Uani 1 1 d . . . C4 C 0.0229(5) -0.0763(9) 0.6204(3) 0.0314(11) Uani 1 1 d . . . H4 H -0.0414 -0.2104 0.6010 0.038 Uiso 1 1 calc R . . C5 C 0.1006(5) 0.0045(9) 0.7162(3) 0.0381(12) Uani 1 1 d . . . H5 H 0.0880 -0.0787 0.7607 0.046 Uiso 1 1 calc R . . O1W O 0.4582(6) 0.7669(6) 0.7729(4) 0.0631(14) Uani 1 1 d D . . H1WA H 0.4740 0.8479 0.8188 0.095 Uiso 1 1 d RD . . H1WB H 0.4631 0.9053 0.7473 0.095 Uiso 1 1 d RD . . 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 0.0275(4) 0.0251(4) 0.0201(4) -0.00432(18) 0.0081(3) 0.0001(2) P1 0.0268(7) 0.0237(7) 0.0244(6) 0.0004(4) 0.0130(6) -0.0005(5) O1 0.028(2) 0.072(3) 0.0324(18) -0.0019(17) 0.0128(17) 0.0023(17) O2 0.049(2) 0.0296(17) 0.0457(18) 0.0042(15) 0.0348(17) 0.0094(16) O3 0.085(3) 0.0196(16) 0.0331(17) -0.0045(15) 0.0201(19) 0.0071(19) N1 0.024(2) 0.029(2) 0.0205(18) -0.0023(15) 0.0088(16) -0.0018(16) C1 0.041(3) 0.037(3) 0.029(2) -0.007(2) 0.013(2) -0.017(2) C2 0.048(3) 0.038(3) 0.022(2) -0.0066(19) 0.019(2) -0.017(2) C3 0.017(2) 0.022(2) 0.0222(19) -0.0035(17) 0.0048(16) -0.0008(18) C4 0.030(2) 0.033(3) 0.027(2) -0.0045(19) 0.013(2) -0.014(2) C5 0.040(3) 0.041(3) 0.022(2) -0.001(2) 0.011(2) -0.012(2) O1W 0.085(4) 0.049(2) 0.068(3) -0.021(2) 0.051(3) -0.023(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 Zn1 O3 1.909(3) 3_667 ? Zn1 O1 1.925(4) . ? Zn1 O2 1.927(3) 3_657 ? Zn1 N1 2.047(4) . ? P1 O3 1.497(4) . ? P1 O1 1.500(4) . ? P1 O2 1.518(3) . ? O2 Zn1 1.927(3) 3_657 ? O3 Zn1 1.909(3) 3_667 ? N1 C1 1.322(6) . ? N1 C5 1.340(6) . ? C1 C2 1.382(7) . ? C2 C3 1.385(6) . ? C3 C4 1.385(6) . ? C3 C3 1.499(8) 3_556 ? C4 C5 1.370(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O1 113.90(19) 3_667 . ? O3 Zn1 O2 110.26(16) 3_667 3_657 ? O1 Zn1 O2 115.51(15) . 3_657 ? O3 Zn1 N1 108.19(14) 3_667 . ? O1 Zn1 N1 101.36(16) . . ? O2 Zn1 N1 106.74(15) 3_657 . ? O3 P1 O1 114.5(2) . . ? O3 P1 O2 109.86(19) . . ? O1 P1 O2 112.3(2) . . ? P1 O1 Zn1 136.3(3) . . ? P1 O2 Zn1 123.2(2) . 3_657 ? P1 O3 Zn1 135.7(2) . 3_667 ? C1 N1 C5 117.6(4) . . ? C1 N1 Zn1 119.5(3) . . ? C5 N1 Zn1 122.3(3) . . ? N1 C1 C2 122.9(5) . . ? C1 C2 C3 119.8(5) . . ? C4 C3 C2 116.9(4) . . ? C4 C3 C3 122.0(5) . 3_556 ? C2 C3 C3 121.1(5) . 3_556 ? C5 C4 C3 119.9(4) . . ? N1 C5 C4 122.9(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.763 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.145 _database_code_depnum_ccdc_archive 'CCDC 940446' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H15 N2 Ni O10 P' _chemical_formula_weight 412.92 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' Ni Ni 0.3393 1.1124 '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' 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' _cell_length_a 16.696 _cell_length_b 14.997 _cell_length_c 7.400 _cell_angle_alpha 90.00 _cell_angle_beta 104.42 _cell_angle_gamma 90.00 _cell_volume 1794.5 _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4250 _cell_measurement_theta_min 1.85 _cell_measurement_theta_max 27.82 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.692 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details SADABS _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 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5786 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetl/netI 0.0584 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.82 _reflns_number_total 4250 _reflns_number_gt 3074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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. The hydrogen atoms bonded to these non-coordinated water molecules were not located. The O(8) atom is found to be disordered. ; _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^)+(0.0990P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 3402 _refine_ls_number_parameters 239 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1487 _refine_ls_wR_factor_gt 0.1455 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.035 _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 Ni1 Ni 0.31075(3) 0.24110(4) 0.22470(8) 0.02333(18) Uani 1 1 d . . . C1 C 0.4797(4) 0.1729(4) 0.2344(10) 0.0386(14) Uani 1 1 d . . . H1 H 0.4905 0.2336 0.2321 0.046 Uiso 1 1 calc R . . C2 C 0.5437(4) 0.1146(4) 0.2398(10) 0.0388(15) Uani 1 1 d . . . H2 H 0.5961 0.1358 0.2397 0.047 Uiso 1 1 calc R . . C3 C 0.5291(3) 0.0233(4) 0.2453(8) 0.0285(11) Uani 1 1 d . . . C4 C 0.4495(4) -0.0020(4) 0.2471(10) 0.0383(14) Uani 1 1 d . . . H4 H 0.4365 -0.0621 0.2528 0.046 Uiso 1 1 calc R . . C5 C 0.3899(3) 0.0615(4) 0.2403(10) 0.0363(13) Uani 1 1 d . . . H5 H 0.3368 0.0429 0.2414 0.044 Uiso 1 1 calc R . . C6 C 0.5953(3) -0.0423(4) 0.2436(8) 0.0302(12) Uani 1 1 d . . . C7 C 0.1750(4) 0.4832(4) 0.2543(10) 0.0395(15) Uani 1 1 d . . . H7 H 0.1896 0.5431 0.2671 0.047 Uiso 1 1 calc R . . C8 C 0.2337(4) 0.4194(4) 0.2460(10) 0.0377(14) Uani 1 1 d . . . H8 H 0.2876 0.4381 0.2539 0.045 Uiso 1 1 calc R . . C9 C 0.1407(4) 0.3080(4) 0.2173(11) 0.0444(16) Uani 1 1 d . . . H9 H 0.1279 0.2476 0.2040 0.053 Uiso 1 1 calc R . . C10 C 0.0788(4) 0.3682(4) 0.2258(11) 0.0442(16) Uani 1 1 d . . . H10 H 0.0255 0.3477 0.2193 0.053 Uiso 1 1 calc R . . N1 N 0.4040(3) 0.1478(3) 0.2323(7) 0.0298(10) Uani 1 1 d . . . N2 N 0.2174(3) 0.3335(3) 0.2276(7) 0.0307(10) Uani 1 1 d . . . O1 O 0.3486(2) 0.3150(3) 0.0274(5) 0.0309(9) Uani 1 1 d . . . O2 O 0.3614(3) 0.3817(3) -0.2736(6) 0.0415(10) Uani 1 1 d . . . O3 O 0.2550(3) 0.2608(3) -0.2730(6) 0.0500(13) Uani 1 1 d . . . O4W O 0.3937(3) 0.3118(3) 0.4283(6) 0.0326(9) Uani 1 1 d D . . H4WA H 0.387(4) 0.332(5) 0.524(7) 0.049 Uiso 1 1 d D . . H4WB H 0.443(3) 0.343(5) 0.432(9) 0.049 Uiso 1 1 d D . . O5W O 0.2743(3) 0.1698(3) 0.4308(6) 0.0326(8) Uani 1 1 d D . . H5WA H 0.282(5) 0.204(4) 0.519(9) 0.049 Uiso 1 1 d D . . H5WB H 0.238(4) 0.130(4) 0.392(10) 0.049 Uiso 1 1 d D . . O6W O 0.2361(3) 0.1627(3) 0.0152(6) 0.0388(10) Uani 1 1 d D . . H6WA H 0.237(5) 0.162(6) -0.102(6) 0.058 Uiso 1 1 d D . . H6WB H 0.189(3) 0.143(5) -0.037(10) 0.058 Uiso 1 1 d D . . O7W O 0.4695(3) 0.4256(4) 0.2087(8) 0.0512(12) Uani 1 1 d . . . O8W O 0.1452(8) 0.0574(10) 0.391(4) 0.054(6) Uiso 0.43(5) 1 d P A 1 O8W' O 0.1403(9) 0.0628(10) 0.305(4) 0.079(6) Uiso 0.57(5) 1 d P A 2 O9W O 0.0753(4) 0.2520(7) 0.6551(11) 0.096(2) Uani 1 1 d . . . O10W O 0.0650(5) 0.1085(6) 0.9082(17) 0.123(3) Uani 1 1 d . . . P1 P 0.30397(9) 0.33826(11) -0.17087(19) 0.0310(3) Uani 1 1 d . . . H1P H 0.239(4) 0.393(5) -0.188(10) 0.05(2) 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 Ni1 0.0195(3) 0.0217(3) 0.0291(3) -0.0013(3) 0.0066(2) 0.0062(3) C1 0.029(3) 0.026(3) 0.058(4) -0.001(3) 0.005(3) 0.004(2) C2 0.023(3) 0.024(3) 0.067(4) -0.005(3) 0.009(3) 0.004(2) C3 0.029(3) 0.023(3) 0.032(3) -0.005(2) 0.006(2) 0.008(2) C4 0.030(3) 0.024(3) 0.064(4) 0.004(3) 0.018(3) 0.004(2) C5 0.023(3) 0.030(3) 0.060(4) 0.000(3) 0.017(3) 0.004(2) C6 0.025(3) 0.032(3) 0.030(3) 0.001(2) 0.002(2) 0.013(2) C7 0.029(3) 0.024(3) 0.065(4) -0.003(3) 0.011(3) 0.005(2) C8 0.025(3) 0.026(3) 0.065(4) -0.005(3) 0.017(3) 0.004(2) C9 0.032(3) 0.028(3) 0.077(5) -0.003(3) 0.022(3) 0.006(2) C10 0.022(3) 0.030(3) 0.083(5) 0.005(3) 0.017(3) 0.005(2) N1 0.024(2) 0.027(2) 0.038(3) -0.003(2) 0.0077(18) 0.0090(18) N2 0.025(2) 0.027(2) 0.041(3) 0.001(2) 0.0091(19) 0.0084(19) O1 0.031(2) 0.033(2) 0.029(2) 0.0002(17) 0.0101(15) 0.0020(17) O2 0.046(3) 0.046(3) 0.036(2) -0.0008(19) 0.0153(19) -0.003(2) O3 0.056(3) 0.061(4) 0.035(2) -0.013(2) 0.0141(19) -0.024(2) O4W 0.033(2) 0.035(2) 0.031(2) -0.0067(17) 0.0083(16) -0.0007(17) O5W 0.033(2) 0.032(2) 0.035(2) 0.0004(18) 0.0113(17) 0.0010(18) O6W 0.033(2) 0.041(3) 0.039(2) -0.006(2) 0.0021(18) -0.0025(19) O7W 0.043(3) 0.046(3) 0.066(3) -0.008(2) 0.016(2) -0.004(2) O9W 0.066(4) 0.125(7) 0.098(5) 0.026(6) 0.022(3) 0.008(5) O10W 0.098(6) 0.102(7) 0.181(10) -0.007(7) 0.055(6) -0.022(5) P1 0.0296(7) 0.0386(8) 0.0257(6) -0.0016(6) 0.0087(5) 0.0036(6) _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 Ni1 O1 2.054(4) . ? Ni1 O4W 2.067(4) . ? Ni1 O5W 2.074(4) . ? Ni1 N1 2.084(4) . ? Ni1 N2 2.089(4) . ? Ni1 O6W 2.092(4) . ? C1 N1 1.315(8) . ? C1 C2 1.374(8) . ? C2 C3 1.393(8) . ? C3 C4 1.385(8) . ? C3 C6 1.482(6) . ? C4 C5 1.370(8) . ? C5 N1 1.319(8) . ? C6 C7 1.368(8) 3_545 ? C6 C10 1.369(9) 3_545 ? C7 C6 1.368(8) 3_455 ? C7 C8 1.382(8) . ? C8 N2 1.316(8) . ? C9 N2 1.320(8) . ? C9 C10 1.387(8) . ? C10 C6 1.369(9) 3_455 ? O1 P1 1.511(4) . ? O2 P1 1.512(5) . ? O3 P1 1.510(5) . ? 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 Ni1 O4W 88.42(16) . . ? O1 Ni1 O5W 178.01(18) . . ? O4W Ni1 O5W 89.68(17) . . ? O1 Ni1 N1 91.27(18) . . ? O4W Ni1 N1 87.98(18) . . ? O5W Ni1 N1 89.28(18) . . ? O1 Ni1 N2 90.64(17) . . ? O4W Ni1 N2 91.02(18) . . ? O5W Ni1 N2 88.78(18) . . ? N1 Ni1 N2 177.8(2) . . ? O1 Ni1 O6W 90.47(17) . . ? O4W Ni1 O6W 174.73(18) . . ? O5W Ni1 O6W 91.47(18) . . ? N1 Ni1 O6W 86.89(18) . . ? N2 Ni1 O6W 94.14(19) . . ? N1 C1 C2 123.9(6) . . ? C1 C2 C3 119.0(6) . . ? C4 C3 C2 116.4(5) . . ? C4 C3 C6 122.5(5) . . ? C2 C3 C6 121.0(5) . . ? C5 C4 C3 120.0(6) . . ? N1 C5 C4 123.2(5) . . ? C7 C6 C10 116.7(5) 3_545 3_545 ? C7 C6 C3 122.0(5) 3_545 . ? C10 C6 C3 121.2(5) 3_545 . ? C6 C7 C8 119.6(6) 3_455 . ? N2 C8 C7 123.5(6) . . ? N2 C9 C10 122.2(6) . . ? C6 C10 C9 120.5(6) 3_455 . ? C1 N1 C5 117.6(5) . . ? C1 N1 Ni1 121.2(4) . . ? C5 N1 Ni1 121.3(4) . . ? C8 N2 C9 117.5(5) . . ? C8 N2 Ni1 121.0(4) . . ? C9 N2 Ni1 121.5(4) . . ? P1 O1 Ni1 130.6(2) . . ? O3 P1 O1 112.5(3) . . ? O3 P1 O2 114.3(3) . . ? O1 P1 O2 111.5(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.82 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.578 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.121 _database_code_depnum_ccdc_archive 'CCDC 940447' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 Co2 N4 O21 P2' _chemical_formula_weight 842.28 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' Co Co 0.3494 0.9721 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' 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' _cell_length_a 17.189(5) _cell_length_b 14.748(5) _cell_length_c 7.469(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.047(5) _cell_angle_gamma 90.00 _cell_volume 1864.4(15) _cell_formula_units_Z 2 _cell_measurement_temperature 195(2) _cell_measurement_reflns_used 3690 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 26.02 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 1.057 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.786 _exptl_absorpt_correction_T_max 0.872 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 195(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5873 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_unetl/netI 0.0755 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3690 _reflns_number_gt 3295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction,2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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. The hydrogen atoms bonded to these non-coordinated water molecules were not located. ; _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^)+(0.0735P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.96(2) _refine_ls_number_reflns 3606 _refine_ls_number_parameters 245 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1285 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _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 0.81556(4) 0.46921(4) 0.73132(8) 0.01737(18) Uani 1 1 d . . . C1 C 0.8962(3) 0.2861(4) 0.7418(8) 0.0300(13) Uani 1 1 d . . . H1 H 0.8446 0.2664 0.7393 0.036 Uiso 1 1 calc R . . C2 C 0.9539(3) 0.2221(4) 0.7477(8) 0.0274(13) Uani 1 1 d . . . H2 H 0.9416 0.1608 0.7502 0.033 Uiso 1 1 calc R . . C3 C 1.0328(3) 0.2506(3) 0.7499(7) 0.0219(11) Uani 1 1 d . . . C4 C 1.0455(4) 0.3429(4) 0.7455(10) 0.0387(16) Uani 1 1 d . . . H4 H 1.0962 0.3654 0.7470 0.046 Uiso 1 1 calc R . . C5 C 0.9821(3) 0.4022(4) 0.7389(10) 0.0351(15) Uani 1 1 d . . . H5 H 0.9916 0.4642 0.7340 0.042 Uiso 1 1 calc R . . C6 C 0.6456(4) 0.5335(4) 0.7290(10) 0.0362(15) Uani 1 1 d . . . H6 H 0.6348 0.4718 0.7171 0.043 Uiso 1 1 calc R . . C7 C 0.5837(4) 0.5920(4) 0.7358(10) 0.0360(15) Uani 1 1 d . . . H7 H 0.5328 0.5695 0.7316 0.043 Uiso 1 1 calc R . . C8 C 1.0975(3) 0.1846(3) 0.7488(7) 0.0215(11) Uani 1 1 d . . . C9 C 1.1745(3) 0.2130(4) 0.7589(9) 0.0314(14) Uani 1 1 d . . . H9 H 1.1869 0.2743 0.7707 0.038 Uiso 1 1 calc R . . C10 C 0.7327(4) 0.6504(4) 0.7515(9) 0.0340(15) Uani 1 1 d . . . H10 H 0.7840 0.6714 0.7557 0.041 Uiso 1 1 calc R . . N1 N 0.9092(3) 0.3747(3) 0.7392(6) 0.0232(10) Uani 1 1 d . . . N2 N 0.7201(3) 0.5604(3) 0.7384(6) 0.0232(9) Uani 1 1 d . . . O1 O 0.8546(2) 0.5470(2) 0.5286(5) 0.0221(8) Uani 1 1 d . . . O2 O 0.8708(2) 0.6184(2) 0.2318(5) 0.0265(8) Uani 1 1 d . . . O3 O 0.7664(2) 0.4955(2) 0.2407(5) 0.0305(9) Uani 1 1 d . . . O4 O 0.7519(2) 0.3844(2) 0.5219(6) 0.0276(9) Uani 1 1 d D . . H4B H 0.709(3) 0.358(4) 0.482(9) 0.041 Uiso 1 1 d D . . H4A H 0.743(4) 0.416(4) 0.427(7) 0.041 Uiso 1 1 d D . . O5 O 0.8918(2) 0.5471(2) 0.9244(5) 0.0257(8) Uani 1 1 d D . . H5A H 0.879(4) 0.574(4) 1.018(7) 0.039 Uiso 1 1 d D . . H5B H 0.909(4) 0.583(4) 0.857(8) 0.039 Uiso 1 1 d D . . O6 O 0.7734(2) 0.3960(2) 0.9414(6) 0.0250(8) Uani 1 1 d D . . H6B H 0.729(3) 0.367(4) 0.916(9) 0.037 Uiso 1 1 d D . . H6A H 0.775(4) 0.420(4) 1.043(7) 0.037 Uiso 1 1 d D . . O1W O 0.5985(3) 0.4864(3) 0.2465(6) 0.0421(11) Uani 1 1 d . . . O2W O 0.8727(3) 0.8013(3) 0.1537(7) 0.0398(11) Uani 1 1 d . . . O3W O 0.9672(2) 0.6610(3) 0.7003(5) 0.0303(9) Uani 1 1 d . . . O4W O 0.5950(3) 0.3247(3) 0.4617(6) 0.0396(10) Uani 1 1 d . . . O5W O 0.5000 0.3771(4) 0.0000 0.0408(15) Uani 1 2 d S . . P1 P 0.81339(8) 0.57363(8) 0.34004(18) 0.0211(3) Uani 1 1 d . . . H1P H 0.756(4) 0.643(4) 0.333(8) 0.032(16) 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 Co1 0.0110(3) 0.0150(3) 0.0262(3) -0.0005(3) 0.0035(2) 0.0034(3) C1 0.014(3) 0.020(2) 0.059(4) 0.000(2) 0.015(3) 0.003(2) C2 0.016(3) 0.025(3) 0.044(3) -0.001(2) 0.011(3) 0.005(2) C3 0.018(3) 0.022(2) 0.025(3) -0.003(2) 0.003(2) 0.007(2) C4 0.018(3) 0.026(3) 0.071(5) -0.003(3) 0.006(3) 0.001(2) C5 0.017(3) 0.017(2) 0.074(5) 0.001(3) 0.014(3) 0.005(2) C6 0.017(3) 0.016(2) 0.076(5) -0.003(3) 0.010(3) 0.000(2) C7 0.011(3) 0.021(3) 0.077(5) -0.003(3) 0.011(3) 0.001(2) C8 0.018(3) 0.020(2) 0.027(3) 0.002(2) 0.006(2) 0.008(2) C9 0.020(3) 0.017(2) 0.058(4) -0.003(2) 0.009(3) 0.001(2) C10 0.014(3) 0.025(3) 0.066(4) 0.001(3) 0.014(3) 0.002(2) N1 0.014(2) 0.0199(19) 0.036(3) -0.0032(18) 0.0054(19) 0.0028(18) N2 0.015(2) 0.0169(19) 0.037(2) 0.0012(18) 0.0029(19) 0.0056(17) O1 0.021(2) 0.0217(17) 0.025(2) -0.0019(14) 0.0071(16) -0.0042(15) O2 0.024(2) 0.0286(18) 0.029(2) 0.0001(15) 0.0087(17) -0.0045(16) O3 0.024(2) 0.043(2) 0.0250(19) -0.0033(16) 0.0055(17) -0.0107(17) O4 0.021(2) 0.024(2) 0.035(2) -0.0013(16) -0.0016(18) -0.0035(16) O5 0.024(2) 0.0271(19) 0.028(2) -0.0065(16) 0.0097(17) -0.0025(16) O6 0.020(2) 0.0251(18) 0.030(2) 0.0025(16) 0.0047(17) -0.0021(16) O1W 0.026(2) 0.043(3) 0.054(3) 0.003(2) -0.0049(19) 0.0076(19) O2W 0.031(3) 0.030(2) 0.061(3) 0.008(2) 0.017(2) 0.0065(18) O3W 0.024(2) 0.031(2) 0.036(2) -0.0033(17) 0.0060(17) -0.0019(16) O4W 0.029(3) 0.040(2) 0.051(3) -0.001(2) 0.010(2) -0.0140(19) O5W 0.033(4) 0.042(3) 0.044(4) 0.000 -0.002(3) 0.000 P1 0.0164(7) 0.0238(6) 0.0235(7) -0.0005(5) 0.0051(5) -0.0003(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 Co1 O1 2.101(4) . ? Co1 O5 2.111(4) . ? Co1 N1 2.122(4) . ? Co1 N2 2.130(4) . ? Co1 O6 2.134(4) . ? Co1 O4 2.147(4) . ? C1 N1 1.326(7) . ? C1 C2 1.365(7) . ? C1 H1 0.9300 . ? C2 C3 1.417(8) . ? C2 H2 0.9300 . ? C3 C4 1.380(8) . ? C3 C8 1.480(6) . ? C4 C5 1.392(8) . ? C4 H4 0.9300 . ? C5 N1 1.318(7) . ? C5 H5 0.9300 . ? C6 N2 1.330(8) . ? C6 C7 1.379(8) . ? C6 H6 0.9300 . ? C7 C8 1.387(7) 3_455 ? C7 H7 0.9300 . ? C8 C9 1.377(8) . ? C8 C7 1.387(7) 3_545 ? C9 C10 1.369(8) 3_545 ? C9 H9 0.9300 . ? C10 N2 1.345(7) . ? C10 C9 1.369(8) 3_455 ? C10 H10 0.9300 . ? O1 P1 1.514(4) . ? O2 P1 1.531(4) . ? O3 P1 1.523(4) . ? O4 H4B 0.84(4) . ? O4 H4A 0.84(4) . ? O5 H5A 0.86(4) . ? O5 H5B 0.82(4) . ? O6 H6B 0.86(4) . ? O6 H6A 0.83(4) . ? P1 H1P 1.41(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O5 87.54(15) . . ? O1 Co1 N1 92.45(16) . . ? O5 Co1 N1 87.79(17) . . ? O1 Co1 N2 91.00(16) . . ? O5 Co1 N2 91.62(16) . . ? N1 Co1 N2 176.47(18) . . ? O1 Co1 O6 177.25(15) . . ? O5 Co1 O6 91.34(16) . . ? N1 Co1 O6 90.02(16) . . ? N2 Co1 O6 86.51(16) . . ? O1 Co1 O4 88.81(15) . . ? O5 Co1 O4 172.38(16) . . ? N1 Co1 O4 85.69(17) . . ? N2 Co1 O4 95.13(17) . . ? O6 Co1 O4 92.59(16) . . ? N1 C1 C2 124.0(5) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 118.9(5) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 116.6(5) . . ? C4 C3 C8 121.7(5) . . ? C2 C3 C8 121.6(4) . . ? C3 C4 C5 119.6(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 123.1(5) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? N2 C6 C7 123.6(5) . . ? N2 C6 H6 118.2 . . ? C7 C6 H6 118.2 . . ? C6 C7 C8 119.6(5) . 3_455 ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 3_455 . ? C9 C8 C7 117.1(5) . 3_545 ? C9 C8 C3 121.1(5) . . ? C7 C8 C3 121.9(5) 3_545 . ? C10 C9 C8 119.6(5) 3_545 . ? C10 C9 H9 120.2 3_545 . ? C8 C9 H9 120.2 . . ? N2 C10 C9 123.9(5) . 3_455 ? N2 C10 H10 118.0 . . ? C9 C10 H10 118.0 3_455 . ? C5 N1 C1 117.8(5) . . ? C5 N1 Co1 120.9(4) . . ? C1 N1 Co1 121.2(4) . . ? C6 N2 C10 116.1(5) . . ? C6 N2 Co1 123.3(3) . . ? C10 N2 Co1 120.7(4) . . ? P1 O1 Co1 131.0(2) . . ? Co1 O4 H4B 146(5) . . ? Co1 O4 H4A 107(5) . . ? H4B O4 H4A 86(6) . . ? Co1 O5 H5A 126(4) . . ? Co1 O5 H5B 100(5) . . ? H5A O5 H5B 112(6) . . ? Co1 O6 H6B 119(4) . . ? Co1 O6 H6A 119(5) . . ? H6B O6 H6A 107(7) . . ? O1 P1 O3 112.3(2) . . ? O1 P1 O2 111.3(2) . . ? O3 P1 O2 113.9(2) . . ? O1 P1 H1P 116(2) . . ? O3 P1 H1P 103(2) . . ? O2 P1 H1P 100(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.5(10) . . . . ? C1 C2 C3 C4 -0.1(9) . . . . ? C1 C2 C3 C8 -177.5(5) . . . . ? C2 C3 C4 C5 -0.1(10) . . . . ? C8 C3 C4 C5 177.3(6) . . . . ? C3 C4 C5 N1 1.0(11) . . . . ? N2 C6 C7 C8 1.6(11) . . . 3_455 ? C4 C3 C8 C9 5.6(9) . . . . ? C2 C3 C8 C9 -177.2(6) . . . . ? C4 C3 C8 C7 -173.7(7) . . . 3_545 ? C2 C3 C8 C7 3.5(8) . . . 3_545 ? C7 C8 C9 C10 1.5(9) 3_545 . . 3_545 ? C3 C8 C9 C10 -177.8(6) . . . 3_545 ? C4 C5 N1 C1 -1.6(10) . . . . ? C4 C5 N1 Co1 179.4(5) . . . . ? C2 C1 N1 C5 1.4(10) . . . . ? C2 C1 N1 Co1 -179.7(5) . . . . ? O1 Co1 N1 C5 44.1(5) . . . . ? O5 Co1 N1 C5 -43.3(5) . . . . ? N2 Co1 N1 C5 -124(3) . . . . ? O6 Co1 N1 C5 -134.6(5) . . . . ? O4 Co1 N1 C5 132.8(5) . . . . ? O1 Co1 N1 C1 -134.8(5) . . . . ? O5 Co1 N1 C1 137.8(5) . . . . ? N2 Co1 N1 C1 57(3) . . . . ? O6 Co1 N1 C1 46.4(5) . . . . ? O4 Co1 N1 C1 -46.2(5) . . . . ? C7 C6 N2 C10 -1.4(10) . . . . ? C7 C6 N2 Co1 179.2(5) . . . . ? C9 C10 N2 C6 1.3(10) 3_455 . . . ? C9 C10 N2 Co1 -179.2(5) 3_455 . . . ? O1 Co1 N2 C6 130.3(5) . . . . ? O5 Co1 N2 C6 -142.1(5) . . . . ? N1 Co1 N2 C6 -62(3) . . . . ? O6 Co1 N2 C6 -50.9(5) . . . . ? O4 Co1 N2 C6 41.4(5) . . . . ? O1 Co1 N2 C10 -49.1(5) . . . . ? O5 Co1 N2 C10 38.4(5) . . . . ? N1 Co1 N2 C10 119(3) . . . . ? O6 Co1 N2 C10 129.7(5) . . . . ? O4 Co1 N2 C10 -138.0(5) . . . . ? O5 Co1 O1 P1 -150.5(3) . . . . ? N1 Co1 O1 P1 121.9(3) . . . . ? N2 Co1 O1 P1 -58.9(3) . . . . ? O6 Co1 O1 P1 -84(4) . . . . ? O4 Co1 O1 P1 36.2(3) . . . . ? Co1 O1 P1 O3 -42.0(3) . . . . ? Co1 O1 P1 O2 -171.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.196 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 940448' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H42 Co3 N6 O15 P2' _chemical_formula_weight 965.43 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' Co Co 0.3494 0.9721 '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' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 6/m c c' _symmetry_space_group_name_Hall '-P 6 2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z' '-y, x-y, z' '-x, -y, z' '-x+y, -x, z' 'y, -x+y, z' '-y, -x, -z+1/2' 'x-y, -y, -z+1/2' 'x, x-y, -z+1/2' 'y, x, -z+1/2' '-x+y, y, -z+1/2' '-x, -x+y, -z+1/2' '-x, -y, -z' '-x+y, -x, -z' 'y, -x+y, -z' 'x, y, -z' 'x-y, x, -z' '-y, x-y, -z' 'y, x, z-1/2' '-x+y, y, z-1/2' '-x, -x+y, z-1/2' '-y, -x, z-1/2' 'x-y, -y, z-1/2' 'x, x-y, z-1/2' _cell_length_a 11.0320(5) _cell_length_b 11.0320(5) _cell_length_c 22.8380(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2407.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 922 _cell_measurement_theta_min 4.10 _cell_measurement_theta_max 27.08 _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 977.9 _exptl_absorpt_coefficient_mu 1.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.759 _exptl_absorpt_correction_T_max 0.804 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9149 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_unetl/netI 0.0180 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 27.08 _reflns_number_total 922 _reflns_number_gt 722 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction,2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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. The O(4) and O(4b) are found to be disordered. Thermal (SIMU) restraints are placed on these atoms to obtain acceptable ADPs. ; _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^)+(0.0480P)^2^+16.0000P] 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 922 _refine_ls_number_parameters 67 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1584 _refine_ls_wR_factor_gt 0.1503 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.065 _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 0.5000 0.5000 0.0284(4) Uani 1 4 d SD . . P1 P 0.3333 0.6667 0.47793(17) 0.0305(8) Uani 0.50 3 d SP . . O1 O 0.3374(5) 0.5368(5) 0.5000 0.0453(13) Uani 1 2 d S . . O2 O 0.6520(5) 0.7203(5) 0.5000 0.0538(16) Uani 1 2 d SD . . H1C H 0.628(2) 0.7789(18) 0.5000 0.081 Uiso 1 2 d SD . . H1D H 0.7355(13) 0.747(2) 0.5000 0.081 Uiso 1 2 d SD . . N1 N 0.5000 0.5000 0.5948(2) 0.0492(16) Uani 1 2 d S . . C1 C 0.6143(9) 0.5779(9) 0.6251(3) 0.095(3) Uani 1 1 d U . . H1A H 0.6967 0.6341 0.6047 0.115 Uiso 1 1 calc R . . C2 C 0.6196(9) 0.5815(10) 0.6860(3) 0.101(3) Uani 1 1 d U . . H2A H 0.7036 0.6387 0.7052 0.121 Uiso 1 1 calc R . . C3 C 0.5000 0.5000 0.7174(3) 0.062(2) Uani 1 2 d S . . O3 O 1.0000 1.0000 0.7500 0.74(10) Uani 1 12 d S . . O4 O 1.0000 1.0000 0.5644(7) 0.038(4) Uani 0.62(2) 6 d SPU . . O4B O 0.936(5) 1.083(5) 0.5589(19) 0.024(7) Uani 0.063(4) 1 d PU . . 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 0.0255(7) 0.0262(7) 0.0357(6) 0.000 0.000 0.0146(5) P1 0.0243(11) 0.0243(11) 0.0428(18) 0.000 0.000 0.0122(5) O1 0.030(3) 0.025(3) 0.079(4) 0.000 0.000 0.012(2) O2 0.028(3) 0.031(3) 0.101(4) 0.000 0.000 0.014(2) N1 0.041(4) 0.064(5) 0.037(3) 0.000 0.000 0.022(3) C1 0.072(5) 0.125(6) 0.049(3) -0.001(4) -0.001(3) 0.019(4) C2 0.078(5) 0.133(7) 0.050(3) -0.007(4) -0.006(4) 0.021(5) C3 0.067(6) 0.072(6) 0.039(4) 0.000 0.000 0.028(5) O3 1.00(17) 1.00(17) 0.22(7) 0.000 0.000 0.50(8) O4 0.017(4) 0.017(4) 0.080(8) 0.000 0.000 0.0085(18) O4B 0.019(10) 0.018(10) 0.046(11) 0.002(8) -0.004(8) 0.017(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 2.027(5) 13_666 ? Co1 O1 2.027(5) . ? Co1 O2 2.154(5) . ? Co1 O2 2.154(5) 13_666 ? Co1 N1 2.166(6) 13_666 ? Co1 N1 2.166(6) . ? P1 P1 1.008(8) 14_566 ? P1 O1 1.541(5) 14_566 ? P1 O1 1.541(5) 3_665 ? P1 O1 1.541(5) . ? O1 P1 1.541(5) 14_566 ? O2 H1C 0.814(11) . ? O2 H1D 0.814(11) . ? N1 C1 1.313(8) . ? N1 C1 1.313(8) 4_665 ? C1 C2 1.391(9) . ? C1 H1A 0.9300 . ? C2 C3 1.370(9) . ? C2 H2A 0.9300 . ? C3 C2 1.370(9) 4_665 ? C3 C3 1.489(15) 7_666 ? O4 O4B 1.42(4) 3_765 ? O4 O4B 1.42(3) 4_775 ? O4 O4B 1.42(4) 6_565 ? O4 O4B 1.42(4) 2_655 ? O4 O4B 1.42(4) 5_675 ? O4 O4B 1.42(3) . ? O4B O4B 1.41(4) 2_655 ? O4B O4B 1.41(3) 6_565 ? 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 180.000(2) 13_666 . ? O1 Co1 O2 87.6(2) 13_666 . ? O1 Co1 O2 92.41(19) . . ? O1 Co1 O2 92.41(19) 13_666 13_666 ? O1 Co1 O2 87.6(2) . 13_666 ? O2 Co1 O2 180.0 . 13_666 ? O1 Co1 N1 90.0 13_666 13_666 ? O1 Co1 N1 90.0 . 13_666 ? O2 Co1 N1 90.000(1) . 13_666 ? O2 Co1 N1 90.000(1) 13_666 13_666 ? O1 Co1 N1 90.0 13_666 . ? O1 Co1 N1 90.0 . . ? O2 Co1 N1 90.000(1) . . ? O2 Co1 N1 90.000(1) 13_666 . ? N1 Co1 N1 180.000(1) 13_666 . ? P1 P1 O1 70.91(15) 14_566 14_566 ? P1 P1 O1 70.91(15) 14_566 3_665 ? O1 P1 O1 109.85(15) 14_566 3_665 ? P1 P1 O1 70.91(15) 14_566 . ? O1 P1 O1 109.85(15) 14_566 . ? O1 P1 O1 109.85(15) 3_665 . ? P1 O1 P1 38.2(3) 14_566 . ? P1 O1 Co1 128.8(3) 14_566 . ? P1 O1 Co1 128.8(3) . . ? Co1 O2 H1C 121.1(14) . . ? Co1 O2 H1D 120.9(14) . . ? H1C O2 H1D 118(2) . . ? C1 N1 C1 116.4(8) . 4_665 ? C1 N1 Co1 121.8(4) . . ? C1 N1 Co1 121.8(4) 4_665 . ? N1 C1 C2 123.9(7) . . ? N1 C1 H1A 118.0 . . ? C2 C1 H1A 118.0 . . ? C3 C2 C1 119.4(7) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C2 116.9(8) 4_665 . ? C2 C3 C3 121.5(4) 4_665 7_666 ? C2 C3 C3 121.5(4) . 7_666 ? O4B O4 O4B 59.7(2) 3_765 4_775 ? O4B O4 O4B 170(4) 3_765 6_565 ? O4B O4 O4B 119.2(6) 4_775 6_565 ? O4B O4 O4B 59.7(2) 3_765 2_655 ? O4B O4 O4B 119.2(6) 4_775 2_655 ? O4B O4 O4B 119.2(6) 6_565 2_655 ? O4B O4 O4B 119.2(6) 3_765 5_675 ? O4B O4 O4B 59.7(2) 4_775 5_675 ? O4B O4 O4B 59.7(2) 6_565 5_675 ? O4B O4 O4B 170(4) 2_655 5_675 ? O4B O4 O4B 119.2(6) 3_765 . ? O4B O4 O4B 170(4) 4_775 . ? O4B O4 O4B 59.7(2) 6_565 . ? O4B O4 O4B 59.7(2) 2_655 . ? O4B O4 O4B 119.2(6) 5_675 . ? O4B O4B O4B 120.000(12) 2_655 6_565 ? O4B O4B O4 60.13(10) 2_655 . ? O4B O4B O4 60.13(10) 6_565 . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.08 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.885 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 940449'