# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1536 data_global _publ_contact_author_name ; Michael Harmjanz, Michael J. Scott ; _publ_contact_author_address ; Department of Chemistry, University of Florida, Gainesville, FL 32611-7200 ; _publ_contact_author_email mjscott@chem.ufl.edu _publ_requested_journal ' ChemComm' _publ_section_title ; A convenient synthesis of trans-Porphyrins with functionalized meso-naphthyl-substituents ; data_2b _audit_creation_method SHELXL-97 _chemical_name_common 'Compound 2b' _chemical_formula_sum 'C61 H45 Cl3 N4 O3 Zn' _chemical_formula_weight 1053.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 29.539(2) _cell_length_b 29.539(2) _cell_length_c 12.1044(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10561.4(14) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4352 _exptl_absorpt_coefficient_mu 0.667 _exptl_absorpt_correction_type 'Corrected by Sadabs ' _exptl_absorpt_correction_T_min 1.000000 _exptl_absorpt_correction_T_max 0.797582 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 27497 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 24.75 _reflns_number_total 4520 _reflns_number_gt 2954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The porphyrin macrocycle crystallized on an inversion symmetry position, and the Zn atom was disordered across this position with a site occupancy of 0.5. The water molecule coordinated to the zinc was similarly modeled with a site occupancy of 0.5 and hydrogen atoms were not included on this atom. A disordered chloroform molecule occupies a position next to the macrocycle on the side opposite to the zinc atom. Two positions were located for this molecule and they were refined with site occupancies of 0.35 and 0.15, respectively. The thermal parameter of carbon atoms of the disordered solvate were refined istropically and the hydrogen atom on the solvate was not included in the refinement. ; _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^)+(0.1481P)^2^+18.8677P] 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 4520 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.2430 _refine_ls_wR_factor_gt 0.2010 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Zn1 Zn 0.49650(4) 0.51084(3) 0.48039(9) 0.0339(4) Uani 0.50 1 d P . . O1 O 0.46840(15) 0.63303(16) 0.5769(5) 0.0892(13) Uani 1 1 d . . . N1 N 0.45812(11) 0.51658(13) 0.6273(3) 0.0468(10) Uani 1 1 d . . . N2 N 0.45267(11) 0.45263(14) 0.4440(3) 0.0487(10) Uani 1 1 d . . . C1 C 0.50372(16) 0.57917(19) 0.7164(4) 0.0585(14) Uani 1 1 d . . . C2 C 0.46588(14) 0.54594(16) 0.7102(4) 0.0452(11) Uani 1 1 d . . . C3 C 0.43038(16) 0.54500(18) 0.7885(4) 0.0544(13) Uani 1 1 d . . . H3A H 0.4282 0.5627 0.8538 0.065 Uiso 1 1 calc R . . C4 C 0.39978(16) 0.51378(17) 0.7523(4) 0.0504(12) Uani 1 1 d . . . H4A H 0.3723 0.5056 0.7876 0.060 Uiso 1 1 calc R . . C5 C 0.41677(13) 0.49602(15) 0.6524(3) 0.0407(10) Uani 1 1 d . . . C6 C 0.39459(14) 0.46276(15) 0.5892(4) 0.0420(10) Uani 1 1 d . . . C7 C 0.41021(14) 0.44329(16) 0.4918(4) 0.0441(11) Uani 1 1 d . . . C8 C 0.38741(15) 0.41071(17) 0.4268(4) 0.0515(12) Uani 1 1 d . . . H8A H 0.3582 0.3985 0.4406 0.062 Uiso 1 1 calc R . . C9 C 0.41511(15) 0.39997(17) 0.3405(4) 0.0538(13) Uani 1 1 d . . . H9A H 0.4089 0.3791 0.2826 0.065 Uiso 1 1 calc R . . C10 C 0.45501(14) 0.42607(17) 0.3543(4) 0.0485(12) Uani 1 1 d . . . C11 C 0.51275(18) 0.5927(3) 0.8342(6) 0.083(2) Uani 1 1 d . . . C12 C 0.5310(2) 0.5658(3) 0.9201(5) 0.083(2) Uani 1 1 d . . . H12A H 0.5426 0.5366 0.9043 0.099 Uiso 1 1 calc R . . C13 C 0.5318(2) 0.5826(4) 1.0295(6) 0.114(3) Uani 1 1 d . . . H13A H 0.5444 0.5644 1.0864 0.137 Uiso 1 1 calc R . . C14 C 0.5149(2) 0.6243(3) 1.0554(8) 0.111(3) Uani 1 1 d . . . H14A H 0.5163 0.6349 1.1294 0.133 Uiso 1 1 calc R . . C15 C 0.4952(2) 0.6520(3) 0.9712(7) 0.093(3) Uani 1 1 d . . . C16 C 0.4758(3) 0.6927(3) 0.9826(9) 0.110(3) Uani 1 1 d . . . H16A H 0.4755 0.7065 1.0535 0.131 Uiso 1 1 calc R . . C17 C 0.4558(3) 0.7160(3) 0.8928(9) 0.107(3) Uani 1 1 d . . . H17A H 0.4424 0.7447 0.9054 0.128 Uiso 1 1 calc R . . C18 C 0.4553(2) 0.6973(2) 0.7830(8) 0.103(3) Uani 1 1 d . . . H18A H 0.4413 0.7128 0.7232 0.123 Uiso 1 1 calc R . . C19 C 0.47636(19) 0.6553(2) 0.7686(6) 0.0730(18) Uani 1 1 d . . . C20 C 0.49545(18) 0.6329(2) 0.8611(6) 0.079(2) Uani 1 1 d . . . C21 C 0.48003(19) 0.6259(2) 0.6736(6) 0.0745(17) Uani 1 1 d . . . C22 C 0.34973(13) 0.44738(14) 0.6330(3) 0.0382(10) Uani 1 1 d . . . C23 C 0.31032(14) 0.47217(14) 0.6069(3) 0.0386(10) Uani 1 1 d . . . C24 C 0.26914(14) 0.45871(15) 0.6521(4) 0.0421(11) Uani 1 1 d . . . H24A H 0.2425 0.4749 0.6331 0.051 Uiso 1 1 calc R . . C25 C 0.26591(15) 0.42219(16) 0.7246(4) 0.0448(11) Uani 1 1 d . . . C26 C 0.30509(16) 0.39872(16) 0.7498(4) 0.0477(11) Uani 1 1 d . . . H26A H 0.3034 0.3739 0.7996 0.057 Uiso 1 1 calc R . . C27 C 0.34679(15) 0.41023(15) 0.7046(4) 0.0445(11) Uani 1 1 d . . . C28 C 0.31266(15) 0.51295(16) 0.5332(4) 0.0483(11) Uani 1 1 d . . . H28A H 0.2824 0.5261 0.5255 0.072 Uiso 1 1 calc R . . H28B H 0.3240 0.5040 0.4603 0.072 Uiso 1 1 calc R . . H28C H 0.3331 0.5354 0.5657 0.072 Uiso 1 1 calc R . . C29 C 0.22084(18) 0.4086(2) 0.7725(5) 0.0640(15) Uani 1 1 d . . . H29A H 0.2256 0.3923 0.8420 0.096 Uiso 1 1 calc R . . H29B H 0.2049 0.3889 0.7201 0.096 Uiso 1 1 calc R . . H29C H 0.2026 0.4357 0.7864 0.096 Uiso 1 1 calc R . . C30 C 0.38815(18) 0.3826(2) 0.7319(5) 0.0658(15) Uani 1 1 d . . . H30A H 0.4004 0.3694 0.6639 0.099 Uiso 1 1 calc R . . H30B H 0.3799 0.3583 0.7833 0.099 Uiso 1 1 calc R . . H30C H 0.4110 0.4021 0.7660 0.099 Uiso 1 1 calc R . . O101 O 0.4686(2) 0.5691(2) 0.3942(6) 0.0550(17) Uani 0.50 1 d P . . C101 C 0.4262(5) 0.5750(5) 0.3598(11) 0.032(3) Uiso 0.35 1 d P . . Cl1 Cl 0.4102(5) 0.6277(4) 0.3049(12) 0.097(3) Uani 0.35 1 d P . . Cl2 Cl 0.48906(19) 0.5773(2) 0.3270(8) 0.106(2) Uani 0.35 1 d P . . Cl3 Cl 0.4017(2) 0.5367(2) 0.3099(7) 0.116(2) Uani 0.35 1 d P . . C201 C 0.4383(10) 0.5905(11) 0.354(2) 0.026(6) Uiso 0.15 1 d P . . Cl4 Cl 0.4035(6) 0.5647(5) 0.4024(13) 0.106(4) Uani 0.15 1 d P . . Cl5 Cl 0.4738(8) 0.5585(8) 0.251(2) 0.141(7) Uani 0.15 1 d P . . Cl6 Cl 0.4196(10) 0.6415(6) 0.296(3) 0.075(7) Uani 0.15 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 Zn1 0.0250(5) 0.0398(8) 0.0368(8) -0.0124(5) 0.0007(5) 0.0014(5) O1 0.069(3) 0.096(3) 0.103(4) -0.022(3) -0.008(3) 0.014(2) N1 0.0276(18) 0.062(2) 0.051(2) -0.0248(19) -0.0006(16) -0.0003(16) N2 0.0256(18) 0.070(3) 0.051(2) -0.031(2) 0.0015(16) 0.0006(17) C1 0.039(3) 0.077(4) 0.060(3) -0.039(3) 0.005(2) -0.005(2) C2 0.030(2) 0.059(3) 0.047(3) -0.024(2) 0.0006(18) 0.0017(19) C3 0.046(3) 0.068(3) 0.050(3) -0.029(2) 0.007(2) -0.002(2) C4 0.043(3) 0.064(3) 0.045(3) -0.022(2) 0.007(2) -0.003(2) C5 0.028(2) 0.052(3) 0.043(2) -0.017(2) -0.0002(17) 0.0038(19) C6 0.030(2) 0.053(3) 0.043(2) -0.013(2) -0.0029(18) 0.0040(19) C7 0.028(2) 0.057(3) 0.048(3) -0.020(2) -0.0012(18) 0.0003(19) C8 0.032(2) 0.064(3) 0.059(3) -0.025(2) 0.003(2) -0.006(2) C9 0.038(2) 0.065(3) 0.058(3) -0.033(2) -0.001(2) -0.006(2) C10 0.031(2) 0.062(3) 0.052(3) -0.028(2) -0.0011(19) 0.001(2) C11 0.038(3) 0.124(5) 0.087(4) -0.073(4) 0.013(3) -0.017(3) C12 0.055(3) 0.132(6) 0.060(4) -0.042(4) -0.020(3) 0.006(4) C13 0.065(4) 0.199(9) 0.078(5) -0.056(5) -0.012(4) 0.005(5) C14 0.057(4) 0.157(8) 0.119(7) -0.076(6) -0.008(4) -0.001(5) C15 0.040(3) 0.125(6) 0.114(6) -0.084(5) 0.026(4) -0.024(4) C16 0.067(5) 0.122(7) 0.139(8) -0.059(6) 0.022(5) -0.028(5) C17 0.071(5) 0.075(5) 0.175(9) -0.068(6) 0.043(5) -0.017(4) C18 0.066(4) 0.068(4) 0.174(8) -0.046(5) 0.033(5) -0.014(3) C19 0.047(3) 0.058(3) 0.113(5) -0.041(3) 0.018(3) -0.011(3) C20 0.034(3) 0.108(5) 0.094(5) -0.060(4) 0.012(3) -0.020(3) C21 0.043(3) 0.082(4) 0.098(5) -0.027(4) 0.004(3) -0.005(3) C22 0.032(2) 0.044(2) 0.038(2) -0.0138(19) -0.0009(17) 0.0012(18) C23 0.031(2) 0.044(2) 0.040(2) -0.0123(19) -0.0017(17) -0.0018(18) C24 0.032(2) 0.047(3) 0.047(3) -0.016(2) 0.0011(19) -0.0001(18) C25 0.046(3) 0.047(3) 0.041(2) -0.014(2) 0.003(2) -0.008(2) C26 0.056(3) 0.044(3) 0.043(3) -0.008(2) -0.004(2) -0.006(2) C27 0.048(3) 0.044(2) 0.042(2) -0.011(2) -0.007(2) 0.003(2) C28 0.034(2) 0.052(3) 0.058(3) 0.004(2) -0.002(2) -0.001(2) C29 0.058(3) 0.069(3) 0.066(3) -0.011(3) 0.014(3) -0.023(3) C30 0.060(3) 0.066(3) 0.072(4) -0.004(3) -0.014(3) 0.016(3) O101 0.038(4) 0.073(5) 0.055(4) 0.012(4) 0.005(3) 0.005(3) Cl1 0.075(5) 0.119(9) 0.098(6) -0.010(7) -0.023(4) 0.021(6) Cl2 0.053(3) 0.122(5) 0.145(6) 0.049(5) 0.002(4) 0.027(3) Cl3 0.092(4) 0.109(4) 0.148(6) 0.050(4) -0.017(4) -0.002(3) Cl4 0.122(11) 0.098(10) 0.098(9) 0.019(8) 0.010(9) 0.033(8) Cl5 0.129(15) 0.142(16) 0.153(17) 0.015(13) 0.017(13) 0.058(12) Cl6 0.101(18) 0.031(6) 0.093(10) 0.007(6) 0.006(10) 0.027(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 Zn1 Zn1 0.8238(17) 9_666 ? Zn1 N1 2.038(4) 9_666 ? Zn1 N2 2.063(4) 9_666 ? Zn1 N1 2.116(4) . ? Zn1 O101 2.175(7) . ? Zn1 N2 2.197(4) . ? Zn1 Cl2 2.711(7) . ? O1 C21 1.237(8) . ? N1 C2 1.346(5) . ? N1 C5 1.398(5) . ? N1 Zn1 2.038(4) 9_666 ? N2 C10 1.341(5) . ? N2 C7 1.408(6) . ? N2 Zn1 2.063(4) 9_666 ? C1 C2 1.490(7) . ? C1 C10 1.498(6) 9_666 ? C1 C11 1.504(8) . ? C1 C21 1.633(9) . ? C2 C3 1.414(6) . ? C3 C4 1.364(7) . ? C4 C5 1.410(6) . ? C5 C6 1.407(6) . ? C6 C7 1.391(6) . ? C6 C22 1.498(6) . ? C7 C8 1.414(6) . ? C8 C9 1.364(6) . ? C9 C10 1.418(6) . ? C10 C1 1.498(6) 9_666 ? C11 C20 1.333(9) . ? C11 C12 1.415(10) . ? C12 C13 1.414(9) . ? C13 C14 1.366(12) . ? C14 C15 1.432(13) . ? C15 C16 1.337(12) . ? C15 C20 1.448(8) . ? C16 C17 1.415(12) . ? C17 C18 1.439(12) . ? C18 C19 1.400(9) . ? C19 C20 1.418(10) . ? C19 C21 1.446(9) . ? C22 C27 1.401(6) . ? C22 C23 1.411(6) . ? C23 C24 1.392(6) . ? C23 C28 1.500(6) . ? C24 C25 1.394(7) . ? C25 C26 1.383(7) . ? C25 C29 1.506(6) . ? C26 C27 1.390(7) . ? C27 C30 1.506(7) . ? O101 Cl2 1.042(8) . ? O101 C201 1.20(3) . ? O101 C101 1.329(16) . ? O101 Cl5 1.76(2) . ? O101 Cl4 1.928(19) . ? C101 C201 0.58(3) . ? C101 Cl4 0.900(17) . ? C101 Cl3 1.473(18) . ? C101 Cl1 1.757(18) . ? C101 Cl2 1.899(17) . ? C101 Cl5 1.98(2) . ? C101 Cl6 2.12(2) . ? Cl1 Cl6 0.51(3) . ? Cl1 C201 1.50(3) . ? Cl1 Cl4 2.213(19) . ? Cl2 Cl5 1.16(2) . ? Cl2 C201 1.58(3) . ? Cl3 Cl4 1.393(16) . ? Cl3 C201 2.00(3) . ? Cl3 Cl5 2.33(2) . ? C201 Cl4 1.41(3) . ? C201 Cl6 1.75(3) . ? C201 Cl5 1.88(3) . ? 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 Zn1 Zn1 N1 83.93(19) 9_666 9_666 ? Zn1 Zn1 N2 88.2(2) 9_666 9_666 ? N1 Zn1 N2 90.73(14) 9_666 9_666 ? Zn1 Zn1 N1 73.29(19) 9_666 . ? N1 Zn1 N1 157.22(6) 9_666 . ? N2 Zn1 N1 88.59(14) 9_666 . ? Zn1 Zn1 O101 170.8(3) 9_666 . ? N1 Zn1 O101 104.9(2) 9_666 . ? N2 Zn1 O101 94.3(2) 9_666 . ? N1 Zn1 O101 97.9(2) . . ? Zn1 Zn1 N2 69.81(19) 9_666 . ? N1 Zn1 N2 87.04(14) 9_666 . ? N2 Zn1 N2 157.99(6) 9_666 . ? N1 Zn1 N2 85.15(14) . . ? O101 Zn1 N2 107.4(2) . . ? Zn1 Zn1 Cl2 168.0(2) 9_666 . ? N1 Zn1 Cl2 84.4(2) 9_666 . ? N2 Zn1 Cl2 89.1(2) 9_666 . ? N1 Zn1 Cl2 118.3(2) . . ? O101 Zn1 Cl2 21.2(2) . . ? N2 Zn1 Cl2 112.5(2) . . ? C2 N1 C5 105.5(3) . . ? C2 N1 Zn1 128.4(3) . 9_666 ? C5 N1 Zn1 122.8(3) . 9_666 ? C2 N1 Zn1 125.9(3) . . ? C5 N1 Zn1 128.1(3) . . ? Zn1 N1 Zn1 22.78(6) 9_666 . ? C10 N2 C7 105.3(3) . . ? C10 N2 Zn1 128.9(3) . 9_666 ? C7 N2 Zn1 124.7(3) . 9_666 ? C10 N2 Zn1 126.1(3) . . ? C7 N2 Zn1 126.6(3) . . ? Zn1 N2 Zn1 22.01(6) 9_666 . ? C2 C1 C10 120.9(4) . 9_666 ? C2 C1 C11 110.9(5) . . ? C10 C1 C11 115.2(4) 9_666 . ? C2 C1 C21 102.7(4) . . ? C10 C1 C21 104.7(5) 9_666 . ? C11 C1 C21 98.8(5) . . ? N1 C2 C3 111.2(4) . . ? N1 C2 C1 126.2(4) . . ? C3 C2 C1 122.4(4) . . ? C4 C3 C2 106.8(4) . . ? C3 C4 C5 106.9(4) . . ? N1 C5 C6 126.3(4) . . ? N1 C5 C4 109.6(4) . . ? C6 C5 C4 124.1(4) . . ? C7 C6 C5 126.5(4) . . ? C7 C6 C22 117.9(4) . . ? C5 C6 C22 115.6(4) . . ? C6 C7 N2 124.2(4) . . ? C6 C7 C8 126.5(4) . . ? N2 C7 C8 109.2(4) . . ? C9 C8 C7 107.4(4) . . ? C8 C9 C10 106.4(4) . . ? N2 C10 C9 111.8(4) . . ? N2 C10 C1 124.4(4) . 9_666 ? C9 C10 C1 123.5(4) . 9_666 ? C20 C11 C12 117.7(6) . . ? C20 C11 C1 113.6(7) . . ? C12 C11 C1 127.9(6) . . ? C13 C12 C11 119.9(7) . . ? C14 C13 C12 121.6(9) . . ? C13 C14 C15 120.1(7) . . ? C16 C15 C14 128.0(8) . . ? C16 C15 C20 116.6(9) . . ? C14 C15 C20 115.4(7) . . ? C15 C16 C17 122.4(8) . . ? C16 C17 C18 121.9(7) . . ? C19 C18 C17 116.7(9) . . ? C18 C19 C20 119.5(7) . . ? C18 C19 C21 131.7(8) . . ? C20 C19 C21 108.6(6) . . ? C11 C20 C19 112.0(6) . . ? C11 C20 C15 125.1(8) . . ? C19 C20 C15 122.8(7) . . ? O1 C21 C19 129.0(7) . . ? O1 C21 C1 124.3(5) . . ? C19 C21 C1 106.7(6) . . ? C27 C22 C23 119.6(4) . . ? C27 C22 C6 120.7(4) . . ? C23 C22 C6 119.6(4) . . ? C24 C23 C22 119.0(4) . . ? C24 C23 C28 120.2(4) . . ? C22 C23 C28 120.8(4) . . ? C23 C24 C25 121.9(4) . . ? C26 C25 C24 118.0(4) . . ? C26 C25 C29 121.4(5) . . ? C24 C25 C29 120.6(4) . . ? C25 C26 C27 122.2(4) . . ? C26 C27 C22 119.3(4) . . ? C26 C27 C30 120.0(5) . . ? C22 C27 C30 120.6(4) . . ? Cl2 O101 C201 89.6(15) . . ? Cl2 O101 C101 105.8(10) . . ? C201 O101 C101 26.1(13) . . ? Cl2 O101 Cl5 39.3(9) . . ? C201 O101 Cl5 76.2(14) . . ? C101 O101 Cl5 78.4(10) . . ? Cl2 O101 Cl4 129.4(8) . . ? C201 O101 Cl4 46.7(16) . . ? C101 O101 Cl4 24.2(8) . . ? Cl5 O101 Cl4 97.2(10) . . ? Cl2 O101 Zn1 109.8(6) . . ? C201 O101 Zn1 153.6(17) . . ? C101 O101 Zn1 127.7(9) . . ? Cl5 O101 Zn1 107.3(7) . . ? Cl4 O101 Zn1 107.5(5) . . ? C201 C101 Cl4 142(4) . . ? C201 C101 O101 64(3) . . ? Cl4 C101 O101 118.5(17) . . ? C201 C101 Cl3 148(4) . . ? Cl4 C101 Cl3 66.9(15) . . ? O101 C101 Cl3 119.2(10) . . ? C201 C101 Cl1 55(3) . . ? Cl4 C101 Cl1 108.5(15) . . ? O101 C101 Cl1 119.3(13) . . ? Cl3 C101 Cl1 113.2(9) . . ? C201 C101 Cl2 50(3) . . ? Cl4 C101 Cl2 149.4(16) . . ? O101 C101 Cl2 31.9(5) . . ? Cl3 C101 Cl2 114.9(9) . . ? Cl1 C101 Cl2 98.8(10) . . ? C201 C101 Cl5 71(3) . . ? Cl4 C101 Cl5 145.4(19) . . ? O101 C101 Cl5 60.6(10) . . ? Cl3 C101 Cl5 83.5(11) . . ? Cl1 C101 Cl5 99.1(11) . . ? Cl2 C101 Cl5 34.8(8) . . ? C201 C101 Cl6 45(3) . . ? Cl4 C101 Cl6 117.0(17) . . ? O101 C101 Cl6 108.9(14) . . ? Cl3 C101 Cl6 121.1(12) . . ? Cl1 C101 Cl6 10.4(12) . . ? Cl2 C101 Cl6 88.9(11) . . ? Cl5 C101 Cl6 93.0(13) . . ? Cl6 Cl1 C201 112(5) . . ? Cl6 Cl1 C101 131(5) . . ? C201 Cl1 C101 18.6(11) . . ? Cl6 Cl1 Cl4 148(5) . . ? C201 Cl1 Cl4 38.9(12) . . ? C101 Cl1 Cl4 22.7(5) . . ? O101 Cl2 Cl5 106.1(14) . . ? O101 Cl2 C201 49.2(11) . . ? Cl5 Cl2 C201 85.0(14) . . ? O101 Cl2 C101 42.4(6) . . ? Cl5 Cl2 C101 76.6(11) . . ? C201 Cl2 C101 16.3(11) . . ? O101 Cl2 Zn1 49.0(5) . . ? Cl5 Cl2 Zn1 103.0(12) . . ? C201 Cl2 Zn1 96.6(11) . . ? C101 Cl2 Zn1 84.9(5) . . ? Cl4 Cl3 C101 36.5(7) . . ? Cl4 Cl3 C201 44.9(11) . . ? C101 Cl3 C201 8.8(10) . . ? Cl4 Cl3 Cl5 92.6(10) . . ? C101 Cl3 Cl5 57.6(9) . . ? C201 Cl3 Cl5 50.8(10) . . ? C101 C201 O101 89(4) . . ? C101 C201 Cl4 23(3) . . ? O101 C201 Cl4 95(2) . . ? C101 C201 Cl1 106(4) . . ? O101 C201 Cl1 164(3) . . ? Cl4 C201 Cl1 99.1(18) . . ? C101 C201 Cl2 114(4) . . ? O101 C201 Cl2 41.2(9) . . ? Cl4 C201 Cl2 130(2) . . ? Cl1 C201 Cl2 129(2) . . ? C101 C201 Cl6 122(4) . . ? O101 C201 Cl6 149(3) . . ? Cl4 C201 Cl6 113.8(19) . . ? Cl1 C201 Cl6 15.5(13) . . ? Cl2 C201 Cl6 115(2) . . ? C101 C201 Cl5 91(4) . . ? O101 C201 Cl5 65.6(13) . . ? Cl4 C201 Cl5 114(2) . . ? Cl1 C201 Cl5 114.5(17) . . ? Cl2 C201 Cl5 38.0(9) . . ? Cl6 C201 Cl5 110.1(19) . . ? C101 C201 Cl3 23(3) . . ? O101 C201 Cl3 95.2(19) . . ? Cl4 C201 Cl3 44.3(12) . . ? Cl1 C201 Cl3 100.3(16) . . ? Cl2 C201 Cl3 105.1(15) . . ? Cl6 C201 Cl3 114.0(17) . . ? Cl5 C201 Cl3 73.9(13) . . ? C101 Cl4 Cl3 76.7(15) . . ? C101 Cl4 C201 14.8(16) . . ? Cl3 Cl4 C201 90.9(16) . . ? C101 Cl4 O101 37.3(12) . . ? Cl3 Cl4 O101 92.1(9) . . ? C201 Cl4 O101 38.3(12) . . ? C101 Cl4 Cl1 48.9(12) . . ? Cl3 Cl4 Cl1 94.2(9) . . ? C201 Cl4 Cl1 42.0(12) . . ? O101 Cl4 Cl1 80.0(8) . . ? Cl2 Cl5 O101 34.6(8) . . ? Cl2 Cl5 C201 57.0(13) . . ? O101 Cl5 C201 38.2(9) . . ? Cl2 Cl5 C101 68.6(11) . . ? O101 Cl5 C101 41.0(6) . . ? C201 Cl5 C101 17.1(8) . . ? Cl2 Cl5 Cl3 104.3(13) . . ? O101 Cl5 Cl3 70.8(7) . . ? C201 Cl5 Cl3 55.3(12) . . ? C101 Cl5 Cl3 38.9(7) . . ? Cl1 Cl6 C201 53(4) . . ? Cl1 Cl6 C101 39(4) . . ? C201 Cl6 C101 13.5(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.75 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.916 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.082 #===END data_6 _audit_creation_method SHELXL-97 _chemical_name_common 'Compound 6 ' _chemical_formula_sum 'C63 H52 Cl2 N4 O4' _chemical_formula_weight 999.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.7995(13) _cell_length_b 12.7094(7) _cell_length_c 17.6758(9) _cell_angle_alpha 90.00 _cell_angle_beta 115.1680(10) _cell_angle_gamma 90.00 _cell_volume 5245.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type 'Corrected by Sadabs ' _exptl_absorpt_correction_T_min 1.000000 _exptl_absorpt_correction_T_max 0.745917 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _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 11105 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 22.49 _reflns_number_total 3433 _reflns_number_gt 3006 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 porphyrin macrocycle crystallized on an inversion symmetry position as does a disordered dichloromethane solvate molecule. Three positions for the chlorine atoms were located with site occupancies of 0.35, 0.35 and 0.3, respectively. The carbon atom was refined with a site occupancy of 0.5 and the hydrogen atoms on the solvate were not included in the refinement. ; _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^)+(0.1210P)^2^+7.7547P] 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 0.0027(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3433 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1884 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 O1 O -0.17280(12) 1.0715(2) -0.32898(18) 0.0849(9) Uani 1 1 d . . . O2 O -0.11153(9) 0.9483(2) -0.24924(14) 0.0614(7) Uani 1 1 d . . . N1 N -0.18837(10) 0.70254(18) -0.38474(13) 0.0388(6) Uani 1 1 d . . . N2 N -0.22157(9) 0.64105(17) -0.55953(13) 0.0351(6) Uani 1 1 d . . . C1 C -0.21518(11) 0.8164(2) -0.29352(16) 0.0345(7) Uani 1 1 d . . . C2 C -0.18121(12) 0.7403(2) -0.30797(16) 0.0385(7) Uani 1 1 d . . . C3 C -0.13173(13) 0.6897(2) -0.24601(17) 0.0470(8) Uani 1 1 d . . . H3A H -0.1169 0.7007 -0.1886 0.056 Uiso 1 1 calc R . . C4 C -0.11039(13) 0.6234(2) -0.28536(17) 0.0476(8) Uani 1 1 d . . . H4A H -0.0781 0.5812 -0.2599 0.057 Uiso 1 1 calc R . . C5 C -0.14617(12) 0.6294(2) -0.37335(16) 0.0396(7) Uani 1 1 d . . . C6 C -0.13944(12) 0.5720(2) -0.43546(16) 0.0371(7) Uani 1 1 d . . . C7 C -0.17419(11) 0.5788(2) -0.52189(16) 0.0342(6) Uani 1 1 d . . . C8 C -0.16244(12) 0.5242(2) -0.58427(16) 0.0368(7) Uani 1 1 d . . . H8A H -0.1332 0.4759 -0.5745 0.044 Uiso 1 1 calc R . . C9 C -0.20195(12) 0.5564(2) -0.65970(16) 0.0358(7) Uani 1 1 d . . . H9A H -0.2047 0.5354 -0.7116 0.043 Uiso 1 1 calc R . . C10 C -0.23915(11) 0.6297(2) -0.64423(15) 0.0338(7) Uani 1 1 d . . . C11 C -0.20465(11) 0.8341(2) -0.20444(16) 0.0347(6) Uani 1 1 d . . . C12 C -0.21611(12) 0.7518(2) -0.16305(17) 0.0458(8) Uani 1 1 d . . . H12A H -0.2264 0.6870 -0.1897 0.055 Uiso 1 1 calc R . . C13 C -0.21291(14) 0.7623(3) -0.08308(19) 0.0585(9) Uani 1 1 d . . . H13A H -0.2188 0.7040 -0.0558 0.070 Uiso 1 1 calc R . . C14 C -0.20132(14) 0.8565(3) -0.0449(2) 0.0609(10) Uani 1 1 d . . . H14A H -0.2006 0.8636 0.0079 0.073 Uiso 1 1 calc R . . C15 C -0.19021(12) 0.9452(3) -0.08427(18) 0.0501(8) Uani 1 1 d . . . C16 C -0.18131(16) 1.0443(4) -0.0463(2) 0.0716(12) Uani 1 1 d . . . H16A H -0.1832 1.0516 0.0049 0.086 Uiso 1 1 calc R . . C17 C -0.17008(17) 1.1293(4) -0.0823(3) 0.0825(14) Uani 1 1 d . . . H17A H -0.1659 1.1950 -0.0572 0.099 Uiso 1 1 calc R . . C18 C -0.16467(14) 1.1192(3) -0.1577(3) 0.0683(11) Uani 1 1 d . . . H18A H -0.1563 1.1782 -0.1816 0.082 Uiso 1 1 calc R . . C19 C -0.17161(12) 1.0227(2) -0.19701(19) 0.0457(8) Uani 1 1 d . . . C20 C -0.18800(11) 0.9335(2) -0.16306(16) 0.0374(7) Uani 1 1 d . . . C21 C -0.15490(13) 1.0174(3) -0.2677(2) 0.0552(9) Uani 1 1 d . . . C22 C -0.08937(19) 0.9357(5) -0.3110(3) 0.0936(15) Uani 1 1 d . . . H22A H -0.0548 0.8947 -0.2879 0.140 Uiso 1 1 calc R . . H22B H -0.0812 1.0036 -0.3273 0.140 Uiso 1 1 calc R . . H22C H -0.1173 0.9003 -0.3591 0.140 Uiso 1 1 calc R . . C23 C -0.08899(12) 0.4983(2) -0.40785(16) 0.0393(7) Uani 1 1 d . . . C24 C -0.03754(12) 0.5313(3) -0.40863(17) 0.0472(8) Uani 1 1 d . . . C25 C 0.00726(14) 0.4597(3) -0.38763(19) 0.0558(9) Uani 1 1 d . . . H25A H 0.0414 0.4814 -0.3887 0.067 Uiso 1 1 calc R . . C26 C 0.00241(15) 0.3574(3) -0.36525(19) 0.0605(10) Uani 1 1 d . . . C27 C -0.04820(16) 0.3273(3) -0.36260(19) 0.0569(9) Uani 1 1 d . . . H27A H -0.0516 0.2589 -0.3466 0.068 Uiso 1 1 calc R . . C28 C -0.09460(13) 0.3958(2) -0.38314(17) 0.0446(8) Uani 1 1 d . . . C29 C -0.02940(15) 0.6423(3) -0.4303(2) 0.0619(9) Uani 1 1 d . . . H29A H -0.0592 0.6601 -0.4839 0.093 Uiso 1 1 calc R . . H29B H 0.0071 0.6487 -0.4321 0.093 Uiso 1 1 calc R . . H29C H -0.0309 0.6893 -0.3887 0.093 Uiso 1 1 calc R . . C30 C 0.05157(19) 0.2809(4) -0.3439(2) 0.0890(15) Uani 1 1 d . . . H30A H 0.0869 0.3192 -0.3252 0.133 Uiso 1 1 calc R . . H30B H 0.0462 0.2405 -0.3925 0.133 Uiso 1 1 calc R . . H30C H 0.0528 0.2345 -0.3003 0.133 Uiso 1 1 calc R . . C31 C -0.14856(15) 0.3617(3) -0.3772(2) 0.0585(9) Uani 1 1 d . . . H31A H -0.1812 0.3839 -0.4264 0.088 Uiso 1 1 calc R . . H31B H -0.1501 0.3928 -0.3288 0.088 Uiso 1 1 calc R . . H31C H -0.1488 0.2864 -0.3728 0.088 Uiso 1 1 calc R . . C32 C 0.0263(4) 0.9719(8) -0.4639(7) 0.091(3) Uani 0.50 1 d P . . Cl1 Cl 0.05285(11) 0.8557(2) -0.4916(2) 0.0805(9) Uani 0.35 1 d P . . Cl2 Cl 0.0231(2) 1.0490(7) -0.5643(4) 0.1073(19) Uani 0.35 1 d P . . Cl3 Cl 0.0030(3) 1.0514(6) -0.5609(4) 0.101(2) Uani 0.30 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 O1 0.0781(18) 0.090(2) 0.0783(19) 0.0483(16) 0.0257(15) 0.0020(15) O2 0.0434(13) 0.0913(18) 0.0502(13) 0.0116(12) 0.0206(11) 0.0005(12) N1 0.0429(13) 0.0438(13) 0.0270(12) -0.0029(10) 0.0122(10) 0.0080(11) N2 0.0390(13) 0.0385(13) 0.0255(12) -0.0002(9) 0.0115(10) 0.0030(10) C1 0.0395(15) 0.0381(15) 0.0245(14) -0.0008(11) 0.0124(12) 0.0002(12) C2 0.0427(16) 0.0453(16) 0.0244(14) -0.0020(12) 0.0111(12) 0.0055(13) C3 0.0524(18) 0.0583(19) 0.0225(14) -0.0017(13) 0.0083(13) 0.0138(15) C4 0.0490(17) 0.0582(19) 0.0269(15) 0.0008(13) 0.0077(13) 0.0184(15) C5 0.0411(16) 0.0462(17) 0.0276(15) -0.0007(12) 0.0109(12) 0.0081(13) C6 0.0382(15) 0.0425(16) 0.0275(15) 0.0003(12) 0.0110(12) 0.0057(12) C7 0.0370(15) 0.0359(15) 0.0289(14) 0.0011(11) 0.0132(12) 0.0032(12) C8 0.0373(15) 0.0411(16) 0.0310(15) -0.0037(12) 0.0136(13) 0.0034(12) C9 0.0393(15) 0.0413(15) 0.0271(14) -0.0049(11) 0.0144(12) 0.0011(12) C10 0.0379(15) 0.0379(15) 0.0261(14) -0.0025(11) 0.0140(12) -0.0022(12) C11 0.0368(15) 0.0415(15) 0.0255(14) -0.0014(12) 0.0130(12) 0.0013(12) C12 0.0482(17) 0.0527(18) 0.0323(16) 0.0016(13) 0.0130(13) -0.0049(14) C13 0.058(2) 0.081(3) 0.0375(18) 0.0098(17) 0.0218(16) -0.0091(18) C14 0.0513(19) 0.105(3) 0.0320(17) -0.0001(19) 0.0233(15) 0.0012(19) C15 0.0368(16) 0.073(2) 0.0347(17) -0.0186(15) 0.0096(13) 0.0072(14) C16 0.061(2) 0.084(3) 0.054(2) -0.031(2) 0.0086(18) 0.019(2) C17 0.065(2) 0.068(3) 0.077(3) -0.043(2) -0.006(2) 0.017(2) C18 0.0451(19) 0.0419(19) 0.085(3) -0.0047(18) -0.0035(18) -0.0021(15) C19 0.0323(15) 0.0452(18) 0.0477(18) -0.0010(14) 0.0055(13) -0.0002(13) C20 0.0322(15) 0.0445(16) 0.0301(15) -0.0042(12) 0.0081(12) 0.0040(12) C21 0.0390(17) 0.058(2) 0.058(2) 0.0134(17) 0.0099(15) -0.0082(15) C22 0.065(2) 0.159(5) 0.074(3) 0.018(3) 0.046(2) 0.002(3) C23 0.0399(16) 0.0494(17) 0.0242(14) -0.0054(12) 0.0095(12) 0.0085(13) C24 0.0424(17) 0.066(2) 0.0299(15) -0.0109(14) 0.0122(13) 0.0036(15) C25 0.0413(18) 0.088(3) 0.0339(17) -0.0100(17) 0.0124(14) 0.0127(17) C26 0.056(2) 0.088(3) 0.0355(17) -0.0014(17) 0.0170(15) 0.0318(19) C27 0.077(2) 0.0548(19) 0.0357(18) 0.0030(14) 0.0202(17) 0.0240(17) C28 0.0510(18) 0.0489(18) 0.0298(15) -0.0024(13) 0.0132(13) 0.0101(14) C29 0.058(2) 0.074(2) 0.058(2) -0.0084(18) 0.0278(17) -0.0070(18) C30 0.082(3) 0.122(4) 0.060(2) 0.010(2) 0.026(2) 0.060(3) C31 0.066(2) 0.054(2) 0.053(2) 0.0026(15) 0.0238(17) 0.0003(16) C32 0.041(4) 0.092(6) 0.087(6) -0.037(5) -0.022(5) 0.003(4) Cl1 0.0520(15) 0.087(2) 0.096(2) -0.0362(16) 0.0255(15) -0.0185(13) Cl2 0.055(3) 0.179(4) 0.125(3) 0.019(3) 0.075(3) -0.013(3) Cl3 0.064(4) 0.178(5) 0.077(3) 0.057(3) 0.046(3) -0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C21 1.197(4) . ? O2 C21 1.348(4) . ? O2 C22 1.442(4) . ? N1 C2 1.376(3) . ? N1 C5 1.380(4) . ? N2 C7 1.368(3) . ? N2 C10 1.375(3) . ? C1 C2 1.400(4) . ? C1 C10 1.402(4) 7_464 ? C1 C11 1.497(4) . ? C2 C3 1.433(4) . ? C3 C4 1.350(4) . ? C4 C5 1.434(4) . ? C5 C6 1.389(4) . ? C6 C7 1.407(4) . ? C6 C23 1.507(4) . ? C7 C8 1.440(4) . ? C8 C9 1.352(4) . ? C9 C10 1.445(4) . ? C10 C1 1.402(4) 7_464 ? C11 C12 1.378(4) . ? C11 C20 1.432(4) . ? C12 C13 1.387(4) . ? C13 C14 1.345(5) . ? C14 C15 1.417(5) . ? C15 C16 1.400(5) . ? C15 C20 1.426(4) . ? C16 C17 1.347(6) . ? C17 C18 1.403(6) . ? C18 C19 1.383(5) . ? C19 C20 1.428(4) . ? C19 C21 1.486(5) . ? C23 C24 1.398(4) . ? C23 C28 1.400(4) . ? C24 C25 1.392(4) . ? C24 C29 1.500(5) . ? C25 C26 1.381(5) . ? C26 C27 1.380(5) . ? C26 C30 1.513(5) . ? C27 C28 1.398(4) . ? C28 C31 1.504(5) . ? C32 Cl3 1.062(13) 5_574 ? C32 Cl2 1.574(12) 5_574 ? C32 C32 1.583(17) 5_574 ? C32 Cl1 1.783(10) . ? C32 Cl3 1.856(13) . ? C32 Cl2 1.999(16) . ? Cl1 Cl3 2.337(8) 5_574 ? Cl2 Cl3 0.548(6) . ? Cl2 C32 1.574(12) 5_574 ? Cl3 C32 1.062(13) 5_574 ? Cl3 Cl1 2.337(8) 5_574 ? 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 C21 O2 C22 116.4(3) . . ? C2 N1 C5 108.9(2) . . ? C7 N2 C10 106.4(2) . . ? C2 C1 C10 125.2(2) . 7_464 ? C2 C1 C11 116.6(2) . . ? C10 C1 C11 117.9(2) 7_464 . ? N1 C2 C1 126.1(2) . . ? N1 C2 C3 107.4(2) . . ? C1 C2 C3 126.4(2) . . ? C4 C3 C2 108.2(2) . . ? C3 C4 C5 108.1(3) . . ? N1 C5 C6 126.5(2) . . ? N1 C5 C4 107.3(2) . . ? C6 C5 C4 126.2(3) . . ? C5 C6 C7 126.1(2) . . ? C5 C6 C23 116.8(2) . . ? C7 C6 C23 117.0(2) . . ? N2 C7 C6 126.1(2) . . ? N2 C7 C8 110.0(2) . . ? C6 C7 C8 123.9(2) . . ? C9 C8 C7 107.1(2) . . ? C8 C9 C10 106.9(2) . . ? N2 C10 C1 125.6(2) . 7_464 ? N2 C10 C9 109.6(2) . . ? C1 C10 C9 124.8(2) 7_464 . ? C12 C11 C20 118.9(2) . . ? C12 C11 C1 117.4(2) . . ? C20 C11 C1 123.4(2) . . ? C11 C12 C13 122.4(3) . . ? C14 C13 C12 120.1(3) . . ? C13 C14 C15 120.7(3) . . ? C16 C15 C14 120.4(3) . . ? C16 C15 C20 119.8(3) . . ? C14 C15 C20 119.8(3) . . ? C17 C16 C15 121.3(4) . . ? C16 C17 C18 120.2(3) . . ? C19 C18 C17 121.0(4) . . ? C18 C19 C20 119.4(3) . . ? C18 C19 C21 116.1(3) . . ? C20 C19 C21 124.1(3) . . ? C15 C20 C19 118.0(3) . . ? C15 C20 C11 117.6(3) . . ? C19 C20 C11 124.3(2) . . ? O1 C21 O2 123.6(3) . . ? O1 C21 C19 126.6(3) . . ? O2 C21 C19 109.5(3) . . ? C24 C23 C28 120.5(3) . . ? C24 C23 C6 120.2(3) . . ? C28 C23 C6 119.3(3) . . ? C25 C24 C23 119.0(3) . . ? C25 C24 C29 119.5(3) . . ? C23 C24 C29 121.5(3) . . ? C26 C25 C24 121.8(3) . . ? C27 C26 C25 118.2(3) . . ? C27 C26 C30 121.2(4) . . ? C25 C26 C30 120.6(4) . . ? C26 C27 C28 122.4(3) . . ? C27 C28 C23 118.0(3) . . ? C27 C28 C31 121.2(3) . . ? C23 C28 C31 120.8(3) . . ? Cl3 C32 Cl2 8.7(6) 5_574 5_574 ? Cl3 C32 C32 86.8(9) 5_574 5_574 ? Cl2 C32 C32 78.6(9) 5_574 5_574 ? Cl3 C32 Cl1 107.8(9) 5_574 . ? Cl2 C32 Cl1 113.9(7) 5_574 . ? C32 C32 Cl1 116.7(8) 5_574 . ? Cl3 C32 Cl3 121.6(6) 5_574 . ? Cl2 C32 Cl3 113.4(6) 5_574 . ? C32 C32 Cl3 34.8(7) 5_574 . ? Cl1 C32 Cl3 102.0(7) . . ? Cl3 C32 Cl2 137.2(7) 5_574 . ? Cl2 C32 Cl2 129.1(5) 5_574 . ? C32 C32 Cl2 50.5(8) 5_574 . ? Cl1 C32 Cl2 92.1(6) . . ? Cl3 C32 Cl2 15.8(3) . . ? C32 Cl1 Cl3 25.6(5) . 5_574 ? Cl3 Cl2 C32 17.0(11) . 5_574 ? Cl3 Cl2 C32 67.1(12) . . ? C32 Cl2 C32 50.9(5) 5_574 . ? Cl2 Cl3 C32 154.3(17) . 5_574 ? Cl2 Cl3 C32 97.1(14) . . ? C32 Cl3 C32 58.4(6) 5_574 . ? Cl2 Cl3 Cl1 147.6(17) . 5_574 ? C32 Cl3 Cl1 46.6(6) 5_574 5_574 ? C32 Cl3 Cl1 85.4(4) . 5_574 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.745 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.071