#Supplementary Material (ESI) for Chemical Communications #This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Chi Ming Che.' 'Nancy P. Y. Chung' 'Chen-Lung Li.' 'Raymond Sun.' 'Suk-Yu Wong.' _publ_contact_author_name 'ProfD Chi-Ming Che' _publ_contact_author_address ; Department of Chemistry The University of Hong Kong Pokfulam Road HONG KONG ; _publ_contact_author_email CMCHE@HKU.HK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Physiologically Stable Vanadium(IV) Porphyrins as a New Class of Anti-HIV Agents ; data_mar1255 _database_code_depnum_ccdc_archive 'CCDC 268109' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H58 N4 O16 V' _chemical_formula_sum 'C56 H58 N4 O16 V' _chemical_formula_weight 1094.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source V V 0.3005 0.5294 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 16.297(3) _cell_length_b 27.009(5) _cell_length_c 8.878(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.11(3) _cell_angle_gamma 90.00 _cell_volume 3538.5(12) _cell_formula_units_Z 2 _cell_measurement_temperature 253(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.027 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1146 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 253(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 'marresearch IPDS mar300' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5611 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0833 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.32 _reflns_number_total 1976 _reflns_number_gt 1343 _reflns_threshold_expression >2sigma(I) _computing_data_collection Marcontrol _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1952P)^2^+8.5230P] 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 1976 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1442 _refine_ls_R_factor_gt 0.1097 _refine_ls_wR_factor_ref 0.3367 _refine_ls_wR_factor_gt 0.3170 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _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 V1 V 0.4773(3) 0.5000 0.4397(4) 0.0401(13) Uani 0.50 2 d SP . . O1 O 0.4128(9) 0.5000 0.2427(15) 0.037(3) Uani 0.50 2 d SP . . O2 O 0.7234(4) 0.3145(2) 0.0653(7) 0.0637(18) Uani 1 1 d . . . O3 O 0.8438(4) 0.2620(2) 0.3238(7) 0.0647(18) Uani 1 1 d . . . O4 O 0.8696(4) 0.2793(2) 0.6336(7) 0.0582(17) Uani 1 1 d . . . N1 N 0.6112(5) 0.5000 0.4557(10) 0.037(2) Uani 1 2 d S . . N2 N 0.5000 0.4256(3) 0.5000 0.033(2) Uani 1 2 d S . . C1 C 0.7311(5) 0.4747(3) 0.4046(10) 0.048(2) Uani 1 1 d . . . H1 H 0.7725 0.4544 0.3876 0.058 Uiso 1 1 calc R . . C2 C 0.6574(5) 0.4590(3) 0.4348(10) 0.040(2) Uani 1 1 d . . . C3 C 0.6340(5) 0.4101(2) 0.4452(9) 0.0387(19) Uani 1 1 d . . . C4 C 0.5597(5) 0.3945(3) 0.4744(8) 0.0378(19) Uani 1 1 d . . . C5 C 0.5364(5) 0.3436(3) 0.4827(9) 0.042(2) Uani 1 1 d . . . H5 H 0.5659 0.3160 0.4672 0.050 Uiso 1 1 calc R . . C6 C 0.6906(5) 0.3710(3) 0.4125(10) 0.0389(19) Uani 1 1 d . . . C7 C 0.6798(5) 0.3623(3) 0.2541(9) 0.046(2) Uani 1 1 d . . . H7 H 0.6376 0.3808 0.1674 0.055 Uiso 1 1 calc R . . C8 C 0.7305(6) 0.3264(3) 0.2188(12) 0.053(2) Uani 1 1 d . . . C9 C 0.7951(5) 0.2995(3) 0.3510(10) 0.044(2) Uani 1 1 d . . . C10 C 0.8052(5) 0.3083(3) 0.5098(11) 0.046(2) Uani 1 1 d . . . C11 C 0.7528(5) 0.3438(3) 0.5445(9) 0.0383(19) Uani 1 1 d . . . H11 H 0.7594 0.3489 0.6526 0.046 Uiso 1 1 calc R . . C12 C 0.6590(8) 0.3405(4) -0.0774(13) 0.102(4) Uani 1 1 d . . . H12A H 0.5990 0.3356 -0.0848 0.153 Uiso 1 1 calc R . . H12B H 0.6619 0.3281 -0.1762 0.153 Uiso 1 1 calc R . . H12C H 0.6730 0.3753 -0.0662 0.153 Uiso 1 1 calc R . . C13 C 0.9118(8) 0.2785(4) 0.2711(15) 0.093(4) Uani 1 1 d . . . H13A H 0.9455 0.2506 0.2612 0.140 Uiso 1 1 calc R . . H13B H 0.9521 0.3013 0.3516 0.140 Uiso 1 1 calc R . . H13C H 0.8828 0.2948 0.1653 0.140 Uiso 1 1 calc R . . C14 C 0.8804(6) 0.2866(3) 0.7972(12) 0.073(3) Uani 1 1 d . . . H14A H 0.9033 0.3193 0.8330 0.109 Uiso 1 1 calc R . . H14B H 0.9223 0.2627 0.8689 0.109 Uiso 1 1 calc R . . H14C H 0.8229 0.2828 0.8018 0.109 Uiso 1 1 calc R . . O5 O 0.5000 0.5289(13) 0.0000 0.213(16) Uiso 0.50 2 d SP . . O6 O 0.222(4) 0.5000 0.064(8) 0.31(3) Uiso 0.50 2 d SP . . O7 O 0.911(4) 0.4692(17) 0.273(7) 0.20(2) Uiso 0.25 1 d P . . 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 V1 0.043(4) 0.0295(19) 0.059(3) 0.000 0.033(3) 0.000 O1 0.056(9) 0.041(8) 0.020(7) 0.000 0.022(7) 0.000 O2 0.088(5) 0.072(4) 0.036(4) -0.010(3) 0.031(3) 0.019(4) O3 0.079(4) 0.049(4) 0.086(5) 0.002(3) 0.054(4) 0.021(3) O4 0.053(4) 0.068(4) 0.055(4) 0.011(3) 0.024(3) 0.021(3) N1 0.042(5) 0.029(5) 0.047(6) 0.000 0.026(5) 0.000 N2 0.040(5) 0.027(5) 0.043(6) 0.000 0.027(4) 0.000 C1 0.048(5) 0.043(4) 0.066(6) -0.003(4) 0.037(5) 0.006(4) C2 0.043(5) 0.030(4) 0.054(5) 0.001(4) 0.028(4) 0.002(4) C3 0.046(5) 0.027(4) 0.045(5) -0.005(3) 0.022(4) 0.003(4) C4 0.044(5) 0.031(4) 0.043(5) 0.003(3) 0.024(4) 0.000(4) C5 0.043(5) 0.033(4) 0.051(5) -0.003(4) 0.022(4) 0.003(4) C6 0.040(5) 0.027(4) 0.056(6) -0.006(4) 0.027(4) -0.003(4) C7 0.059(6) 0.041(5) 0.042(5) -0.004(4) 0.026(4) 0.011(4) C8 0.053(6) 0.043(5) 0.068(7) -0.002(5) 0.030(5) 0.003(5) C9 0.054(6) 0.041(5) 0.048(6) -0.004(4) 0.032(5) 0.006(4) C10 0.035(5) 0.039(5) 0.063(6) 0.009(4) 0.021(4) 0.008(4) C11 0.044(5) 0.039(4) 0.035(5) -0.002(4) 0.020(4) 0.006(4) C12 0.121(10) 0.114(10) 0.070(8) -0.001(7) 0.040(7) 0.035(8) C13 0.092(8) 0.093(8) 0.138(10) 0.010(7) 0.091(8) 0.023(6) C14 0.067(7) 0.066(7) 0.066(7) 0.010(5) 0.010(5) 0.012(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 V1 V1 1.010(7) 5_666 ? V1 O1 1.614(13) . ? V1 N1 2.020(8) 5_666 ? V1 N2 2.072(7) 5_666 ? V1 N2 2.072(7) . ? V1 N1 2.126(9) . ? O2 C8 1.357(10) . ? O2 C12 1.439(12) . ? O3 C9 1.370(9) . ? O3 C13 1.444(10) . ? O4 C10 1.395(9) . ? O4 C14 1.401(10) . ? N1 C2 1.396(8) 6_565 ? N1 C2 1.396(8) . ? N1 V1 2.020(8) 5_666 ? N2 C4 1.375(8) 2_656 ? N2 C4 1.375(8) . ? N2 V1 2.072(7) 5_666 ? C1 C1 1.365(14) 6_565 ? C1 C2 1.404(10) . ? C2 C3 1.388(9) . ? C3 C4 1.407(9) . ? C3 C6 1.508(10) . ? C4 C5 1.435(10) . ? C5 C5 1.344(14) 2_656 ? C6 C7 1.361(10) . ? C6 C11 1.391(11) . ? C7 C8 1.394(11) . ? C8 C9 1.402(11) . ? C9 C10 1.369(11) . ? C10 C11 1.402(10) . ? O5 O5 1.56(7) 5_665 ? O7 O7 1.66(9) 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 V1 V1 O1 174.6(8) 5_666 . ? V1 V1 N1 81.8(5) 5_666 5_666 ? O1 V1 N1 103.6(6) . 5_666 ? V1 V1 N2 75.89(10) 5_666 5_666 ? O1 V1 N2 104.04(10) . 5_666 ? N1 V1 N2 88.01(13) 5_666 5_666 ? V1 V1 N2 75.89(10) 5_666 . ? O1 V1 N2 104.04(10) . . ? N1 V1 N2 88.01(13) 5_666 . ? N2 V1 N2 151.8(2) 5_666 . ? V1 V1 N1 70.1(5) 5_666 . ? O1 V1 N1 104.5(5) . . ? N1 V1 N1 151.9(2) 5_666 . ? N2 V1 N1 85.25(13) 5_666 . ? N2 V1 N1 85.25(13) . . ? C8 O2 C12 119.2(7) . . ? C9 O3 C13 114.2(6) . . ? C10 O4 C14 117.3(6) . . ? C2 N1 C2 105.1(8) 6_565 . ? C2 N1 V1 126.3(4) 6_565 5_666 ? C2 N1 V1 126.3(4) . 5_666 ? C2 N1 V1 126.0(4) 6_565 . ? C2 N1 V1 126.0(4) . . ? V1 N1 V1 28.1(2) 5_666 . ? C4 N2 C4 104.6(8) 2_656 . ? C4 N2 V1 127.7(4) 2_656 5_666 ? C4 N2 V1 125.1(4) . 5_666 ? C4 N2 V1 125.1(4) 2_656 . ? C4 N2 V1 127.7(4) . . ? V1 N2 V1 28.2(2) 5_666 . ? C1 C1 C2 107.7(4) 6_565 . ? C3 C2 N1 124.6(6) . . ? C3 C2 C1 125.6(6) . . ? N1 C2 C1 109.8(6) . . ? C2 C3 C4 125.4(6) . . ? C2 C3 C6 116.5(6) . . ? C4 C3 C6 118.1(6) . . ? N2 C4 C3 124.9(6) . . ? N2 C4 C5 110.8(6) . . ? C3 C4 C5 124.3(6) . . ? C5 C5 C4 106.8(4) 2_656 . ? C7 C6 C11 120.5(7) . . ? C7 C6 C3 119.8(7) . . ? C11 C6 C3 119.6(7) . . ? C6 C7 C8 121.5(8) . . ? O2 C8 C7 125.8(8) . . ? O2 C8 C9 115.6(7) . . ? C7 C8 C9 118.7(8) . . ? C10 C9 O3 119.0(7) . . ? C10 C9 C8 119.4(7) . . ? O3 C9 C8 121.5(7) . . ? C9 C10 O4 115.8(7) . . ? C9 C10 C11 121.8(7) . . ? O4 C10 C11 122.4(8) . . ? C6 C11 C10 118.1(7) . . ? _diffrn_measured_fraction_theta_max 0.597 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.597 _refine_diff_density_max 1.031 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.213