# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Pandey, Ravindra' 'Alderfer, James L.' 'Dougherty, Thomas J.' 'Li, Guolin' 'Mehta, Ricky' 'Nurco, Daniel J.' 'Smith, Kevin M.' 'Srikrishnan, Thamarapu' 'Tabaczynski, Walter A.' _publ_contact_author_name 'Prof Ravindra K. Pandey' _publ_contact_author_address ; Department of Radiation Biology Division of Radiation Medicine Roswell Park Cancer Institute Elm and Carlton Streets Buffalo NY 14263 USA ; _publ_contact_author_email ravindra.pandey@roswellpark.edu _publ_requested_journal 'Chemical Communications' _publ_section_title ; A novel synthetic route to fused propenochlorin and benzochlorin photodynamic therapy probes ; data_new9n _database_code_CSD 172740 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ni(II)-7-cyano-2,3,7,8,12,13,17,18-octaethyl 10^3^-keto-benzochlorin ; _chemical_name_common 9 _chemical_melting_point ? _chemical_formula_moiety 'C40 H45 N5 Ni O' _chemical_formula_sum 'C40 H45 N5 Ni O' _chemical_formula_weight 670.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.447(3) _cell_length_b 20.780(4) _cell_length_c 13.685(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.93(3) _cell_angle_gamma 90.00 _cell_volume 3495.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 28 _exptl_crystal_description 'plate-like prisms' _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 1.093 _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 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD-4 _diffrn_measurement_method '\w/2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.5 _diffrn_reflns_number 13788 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 74.96 _reflns_number_total 7187 _reflns_number_gt 5464 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 _computing_cell_refinement 'least-squares CAD4 program' _computing_data_reduction XCAD4 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Two ethyl groups were disordered with two sets of positions for each group. Disordered atoms were refined with isotropic thermal parameters. All other non- hydrogen atoms were refined with anisotropic thermal parameters. C8 and C8' (a pyrrole beta carbon at porphyrin macrocycyle position C8) C8A and C8A' (the methylene carbon of the ethyl group attached to C8) C8B and C8B' (the methyl carbon of the ethyl group attached to C8) The occupancies for the two sets of sites for this group were summed to unity. The occupancy ratio for C8-C8A-C8B/C8'-C8A'-C8B' was found to be 0.643/0.357. The isotropic thermal parameters were refined as one free variable for each of the pairs of disordered atom sites. C2A and C2A' (methylene carbon from the ethyl group attached to C2) C2B and C2B' (methyl carbon from the ethyl group attached to C2) The occupancies for the two sets of sites for this group were summed to unity. The occupancy ratio for C2A-C2B/C2A'-C2B' was 0.716/0.284. The isotropic thermal parameters were refined as one free variable for each of the pairs of disordered atom sites. Nine restraints were employed in the refinement of the disordered atom sites. 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^)+(0.0733P)^2^+1.5093P] 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 0.0034(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 7187 _refine_ls_number_parameters 439 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1618 _refine_ls_wR_factor_gt 0.1455 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.003 _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 0.41582(3) 0.376541(19) 0.98326(3) 0.05260(16) Uani 1 1 d . . . N1 N 0.54447(17) 0.34668(10) 1.10103(16) 0.0568(5) Uani 1 1 d . A . N2 N 0.32658(17) 0.32916(10) 1.04066(16) 0.0596(5) Uani 1 1 d . A . N3 N 0.28807(17) 0.39853(11) 0.85710(16) 0.0586(5) Uani 1 1 d . A . N4 N 0.50489(16) 0.42900(9) 0.93371(15) 0.0536(4) Uani 1 1 d . A . N5 N 0.7209(3) 0.38909(18) 1.3990(3) 0.1159(12) Uani 1 1 d . . . O1 O 0.7797(2) 0.21970(16) 1.3772(3) 0.1377(13) Uani 1 1 d . A . C1 C 0.6485(2) 0.36829(13) 1.1314(2) 0.0594(6) Uani 1 1 d . A . C2 C 0.7265(2) 0.33173(15) 1.2293(2) 0.0726(8) Uani 1 1 d D . . C2A C 0.8441(6) 0.3279(5) 1.2426(9) 0.100(5) Uani 0.716(7) 1 d PD A 1 H2A1 H 0.8451 0.3240 1.1724 0.120 Uiso 0.716(7) 1 calc PR A 1 H2A2 H 0.8764 0.2892 1.2823 0.120 Uiso 0.716(7) 1 calc PR A 1 C2B C 0.9146(5) 0.3859(3) 1.3001(6) 0.121(2) Uiso 0.716(7) 1 d PD A 1 H2B1 H 0.8778 0.4250 1.2682 0.182 Uiso 0.716(7) 1 calc PR A 1 H2B2 H 0.9831 0.3838 1.2938 0.182 Uiso 0.716(7) 1 calc PR A 1 H2B3 H 0.9270 0.3850 1.3743 0.182 Uiso 0.716(7) 1 calc PR A 1 C2A' C 0.8457(8) 0.3307(14) 1.2383(19) 0.105(14) Uani 0.284(7) 1 d PD A 2 H2A3 H 0.8445 0.3114 1.1733 0.126 Uiso 0.284(7) 1 calc PR A 2 H2A4 H 0.8686 0.3751 1.2392 0.126 Uiso 0.284(7) 1 calc PR A 2 C2B' C 0.9311(12) 0.2973(9) 1.3300(13) 0.121(2) Uiso 0.284(7) 1 d PD A 2 H2B4 H 0.9333 0.3149 1.3957 0.182 Uiso 0.284(7) 1 calc PR A 2 H2B5 H 1.0004 0.3033 1.3267 0.182 Uiso 0.284(7) 1 calc PR A 2 H2B6 H 0.9147 0.2522 1.3267 0.182 Uiso 0.284(7) 1 calc PR A 2 C2C C 0.7236(3) 0.36364(17) 1.3260(3) 0.0855(10) Uani 1 1 d . A . C3 C 0.6629(2) 0.26831(15) 1.2128(3) 0.0756(8) Uani 1 1 d . A . C3A C 0.6855(3) 0.22538(18) 1.1295(4) 0.1032(12) Uani 1 1 d . . . H3A1 H 0.6751 0.2516 1.0675 0.124 Uiso 1 1 calc R A . H3A2 H 0.7612 0.2123 1.1610 0.124 Uiso 1 1 calc R . . C3B C 0.6165(5) 0.1661(2) 1.0922(5) 0.152(2) Uani 1 1 d . A . H3B1 H 0.6359 0.1359 1.1500 0.228 Uiso 1 1 calc R . . H3B2 H 0.6282 0.1471 1.0339 0.228 Uiso 1 1 calc R . . H3B3 H 0.5412 0.1775 1.0689 0.228 Uiso 1 1 calc R . . C3C C 0.6862(3) 0.22852(17) 1.3132(3) 0.0943(11) Uani 1 1 d . . . C3D C 0.5941(3) 0.19914(19) 1.3216(3) 0.1029(12) Uani 1 1 d . A . H3D H 0.6050 0.1664 1.3713 0.123 Uiso 1 1 calc R . . C3E C 0.4931(3) 0.21727(16) 1.2603(3) 0.0879(10) Uani 1 1 d . . . H3E H 0.4363 0.1951 1.2672 0.105 Uiso 1 1 calc R A . C4 C 0.5488(2) 0.29397(13) 1.1622(2) 0.0634(6) Uani 1 1 d . . . C5 C 0.4654(2) 0.26967(14) 1.1827(2) 0.0685(7) Uani 1 1 d . A . C6 C 0.3587(2) 0.29388(13) 1.1331(2) 0.0644(6) Uani 1 1 d . . . C7 C 0.2680(3) 0.28297(15) 1.1616(3) 0.0765(8) Uani 1 1 d D A . C7A C 0.2712(3) 0.2586(2) 1.2666(3) 0.0995(12) Uani 1 1 d . . . H7A1 H 0.1973 0.2545 1.2611 0.119 Uiso 1 1 calc R A . H7A2 H 0.3038 0.2161 1.2801 0.119 Uiso 1 1 calc R . . C7B C 0.3335(5) 0.3011(3) 1.3587(4) 0.1420(19) Uani 1 1 d . A . H7B1 H 0.4079 0.3034 1.3673 0.213 Uiso 1 1 calc R . . H7B2 H 0.3305 0.2840 1.4226 0.213 Uiso 1 1 calc R . . H7B3 H 0.3023 0.3435 1.3456 0.213 Uiso 1 1 calc R . . C8 C 0.1793(5) 0.3021(3) 1.0743(4) 0.0685(10) Uiso 0.643(6) 1 d PD A 1 C8A C 0.0635(5) 0.3038(3) 1.0657(6) 0.0878(14) Uiso 0.643(6) 1 d PD A 1 H8A1 H 0.0503 0.2668 1.1020 0.105 Uiso 0.643(6) 1 calc PR A 1 H8A2 H 0.0131 0.3020 0.9912 0.105 Uiso 0.643(6) 1 calc PR A 1 C8B C 0.0447(8) 0.3685(5) 1.1188(8) 0.157(3) Uiso 0.643(6) 1 d PD A 1 H8B1 H -0.0293 0.3703 1.1116 0.235 Uiso 0.643(6) 1 calc PR A 1 H8B2 H 0.0593 0.4050 1.0835 0.235 Uiso 0.643(6) 1 calc PR A 1 H8B3 H 0.0928 0.3693 1.1932 0.235 Uiso 0.643(6) 1 calc PR A 1 C8' C 0.1794(8) 0.3148(5) 1.0949(8) 0.0685(10) Uiso 0.357(6) 1 d PD A 2 C8A' C 0.0610(9) 0.3220(6) 1.0882(10) 0.0878(14) Uiso 0.357(6) 1 d PD A 2 H8A3 H 0.0217 0.3570 1.0415 0.105 Uiso 0.357(6) 1 calc PR A 2 H8A4 H 0.0596 0.3274 1.1581 0.105 Uiso 0.357(6) 1 calc PR A 2 C8B' C 0.0174(14) 0.2533(8) 1.0378(14) 0.157(3) Uiso 0.357(6) 1 d PD A 2 H8B4 H 0.0227 0.2495 0.9701 0.235 Uiso 0.357(6) 1 calc PR A 2 H8B5 H -0.0572 0.2486 1.0276 0.235 Uiso 0.357(6) 1 calc PR A 2 H8B6 H 0.0604 0.2203 1.0852 0.235 Uiso 0.357(6) 1 calc PR A 2 C9 C 0.2148(2) 0.33304(15) 1.0045(2) 0.0682(7) Uani 1 1 d . . . C10 C 0.1480(2) 0.35472(16) 0.9054(2) 0.0730(7) Uani 1 1 d . A . H10 H 0.0734 0.3504 0.8852 0.088 Uiso 1 1 calc R . . C11 C 0.1818(2) 0.38227(14) 0.8335(2) 0.0647(6) Uani 1 1 d . . . C12 C 0.1125(2) 0.39902(16) 0.7248(2) 0.0755(8) Uani 1 1 d . A . C12A C -0.0086(3) 0.3881(2) 0.6738(3) 0.1025(12) Uani 1 1 d . . . H12A H -0.0307 0.3811 0.5978 0.123 Uiso 1 1 calc R A . H12B H -0.0255 0.3494 0.7036 0.123 Uiso 1 1 calc R . . C12B C -0.0718(4) 0.4420(3) 0.6892(5) 0.152(2) Uani 1 1 d . A . H12C H -0.0543 0.4472 0.7641 0.228 Uiso 1 1 calc R . . H12D H -0.1481 0.4330 0.6521 0.228 Uiso 1 1 calc R . . H12E H -0.0544 0.4808 0.6614 0.228 Uiso 1 1 calc R . . C13 C 0.1773(2) 0.42655(15) 0.6830(2) 0.0718(7) Uani 1 1 d . . . C13A C 0.1498(3) 0.44839(19) 0.5707(2) 0.0888(10) Uani 1 1 d . A . H13A H 0.1795 0.4911 0.5722 0.107 Uiso 1 1 calc R . . H13B H 0.0714 0.4512 0.5329 0.107 Uiso 1 1 calc R . . C13B C 0.1940(4) 0.4032(3) 0.5105(3) 0.1158(14) Uani 1 1 d . . . H13C H 0.2719 0.4016 0.5460 0.174 Uiso 1 1 calc R A . H13D H 0.1734 0.4186 0.4388 0.174 Uiso 1 1 calc R . . H13E H 0.1647 0.3609 0.5087 0.174 Uiso 1 1 calc R . . C14 C 0.2854(2) 0.42813(13) 0.76581(19) 0.0622(6) Uani 1 1 d . A . C15 C 0.3712(2) 0.46003(14) 0.7595(2) 0.0673(7) Uani 1 1 d . . . H15 H 0.3591 0.4815 0.6960 0.081 Uiso 1 1 calc R A . C16 C 0.4731(2) 0.46287(12) 0.8385(2) 0.0598(6) Uani 1 1 d . A . C17 C 0.5629(2) 0.49756(13) 0.8333(2) 0.0654(6) Uani 1 1 d . . . C17A C 0.5567(3) 0.54144(17) 0.7438(3) 0.0826(9) Uani 1 1 d . A . H17A H 0.4882 0.5646 0.7187 0.099 Uiso 1 1 calc R . . H17B H 0.6148 0.5729 0.7715 0.099 Uiso 1 1 calc R . . C17B C 0.5651(5) 0.5079(3) 0.6516(3) 0.139(2) Uani 1 1 d . . . H17C H 0.6358 0.4886 0.6738 0.208 Uiso 1 1 calc R A . H17D H 0.5547 0.5383 0.5955 0.208 Uiso 1 1 calc R . . H17E H 0.5103 0.4751 0.6259 0.208 Uiso 1 1 calc R . . C18 C 0.6507(2) 0.48394(13) 0.9241(2) 0.0622(6) Uani 1 1 d . A . C18A C 0.7653(2) 0.50230(16) 0.9526(3) 0.0762(8) Uani 1 1 d . . . H18A H 0.8016 0.5075 1.0295 0.091 Uiso 1 1 calc R A . H18B H 0.7673 0.5434 0.9200 0.091 Uiso 1 1 calc R . . C18B C 0.8257(3) 0.4534(3) 0.9170(4) 0.1242(16) Uani 1 1 d . A . H18C H 0.8280 0.4133 0.9526 0.186 Uiso 1 1 calc R . . H18D H 0.8985 0.4683 0.9345 0.186 Uiso 1 1 calc R . . H18E H 0.7892 0.4474 0.8411 0.186 Uiso 1 1 calc R . . C19 C 0.6126(2) 0.44180(11) 0.98517(19) 0.0544(5) Uani 1 1 d . . . C20 C 0.6804(2) 0.41460(13) 1.0814(2) 0.0621(6) Uani 1 1 d . A . H20 H 0.7519 0.4290 1.1133 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0557(3) 0.0505(2) 0.0487(2) 0.00205(16) 0.01819(17) 0.00052(17) N1 0.0587(11) 0.0537(11) 0.0550(11) 0.0027(9) 0.0199(9) -0.0018(9) N2 0.0617(12) 0.0557(11) 0.0573(11) 0.0047(9) 0.0197(9) -0.0027(9) N3 0.0591(12) 0.0588(12) 0.0529(10) 0.0010(9) 0.0177(9) 0.0027(9) N4 0.0607(11) 0.0516(10) 0.0479(9) 0.0007(8) 0.0214(8) 0.0019(9) N5 0.149(3) 0.115(3) 0.0661(17) 0.0021(18) 0.0245(19) -0.013(2) O1 0.0896(18) 0.129(2) 0.147(3) 0.076(2) -0.0007(17) -0.0017(16) C1 0.0573(13) 0.0610(14) 0.0534(12) 0.0028(11) 0.0160(10) -0.0028(11) C2 0.0609(16) 0.0788(19) 0.0659(16) 0.0141(14) 0.0131(12) -0.0024(13) C2A 0.092(7) 0.091(7) 0.106(9) 0.030(6) 0.029(5) 0.006(5) C2A' 0.011(5) 0.16(3) 0.11(2) 0.030(17) -0.007(7) -0.006(8) C2C 0.089(2) 0.081(2) 0.0643(18) 0.0139(16) 0.0084(15) -0.0101(17) C3 0.0701(17) 0.0630(16) 0.0822(18) 0.0148(14) 0.0190(14) 0.0044(13) C3A 0.093(2) 0.078(2) 0.132(3) -0.003(2) 0.039(2) 0.0221(19) C3B 0.177(5) 0.100(3) 0.171(5) -0.035(3) 0.064(4) 0.001(3) C3C 0.082(2) 0.077(2) 0.098(2) 0.0328(18) 0.0095(18) 0.0043(17) C3D 0.099(3) 0.084(2) 0.107(3) 0.045(2) 0.022(2) 0.0008(19) C3E 0.088(2) 0.073(2) 0.092(2) 0.0299(17) 0.0258(18) -0.0022(16) C4 0.0629(15) 0.0566(14) 0.0620(14) 0.0117(11) 0.0164(12) 0.0023(11) C5 0.0710(17) 0.0612(15) 0.0687(15) 0.0135(13) 0.0235(13) -0.0036(13) C6 0.0676(16) 0.0583(14) 0.0646(14) 0.0094(12) 0.0241(12) -0.0072(12) C7 0.0799(19) 0.0712(18) 0.0824(19) 0.0145(15) 0.0368(16) -0.0090(15) C7A 0.107(3) 0.104(3) 0.103(3) 0.043(2) 0.059(2) 0.005(2) C7B 0.194(5) 0.155(5) 0.089(3) 0.020(3) 0.071(3) -0.014(4) C9 0.0590(14) 0.0735(17) 0.0712(16) 0.0074(13) 0.0256(12) -0.0064(12) C10 0.0565(15) 0.0835(19) 0.0724(17) 0.0059(15) 0.0193(13) -0.0015(13) C11 0.0559(14) 0.0688(16) 0.0612(14) 0.0018(12) 0.0153(11) 0.0022(12) C12 0.0653(16) 0.084(2) 0.0640(16) 0.0025(15) 0.0128(13) 0.0048(15) C12A 0.0626(18) 0.149(4) 0.079(2) 0.016(2) 0.0107(16) 0.006(2) C12B 0.085(3) 0.228(7) 0.140(4) 0.031(4) 0.042(3) 0.037(4) C13 0.0684(16) 0.0784(18) 0.0575(14) 0.0054(13) 0.0142(12) 0.0072(14) C13A 0.084(2) 0.106(3) 0.0589(16) 0.0166(17) 0.0111(15) 0.0091(19) C13B 0.112(3) 0.162(4) 0.0656(19) -0.003(2) 0.027(2) 0.011(3) C14 0.0674(15) 0.0622(15) 0.0503(12) 0.0065(11) 0.0170(11) 0.0082(12) C15 0.0759(17) 0.0670(16) 0.0554(14) 0.0101(12) 0.0230(13) 0.0056(13) C16 0.0689(15) 0.0566(14) 0.0546(13) 0.0063(11) 0.0256(11) 0.0032(11) C17 0.0791(17) 0.0605(15) 0.0608(14) 0.0047(12) 0.0326(13) -0.0010(13) C17A 0.100(2) 0.079(2) 0.0737(18) 0.0157(15) 0.0400(17) -0.0068(17) C17B 0.226(6) 0.125(4) 0.084(3) 0.003(2) 0.083(3) -0.017(4) C18 0.0726(16) 0.0560(14) 0.0623(14) -0.0041(11) 0.0318(12) -0.0058(12) C18A 0.0779(19) 0.0747(18) 0.0803(18) 0.0002(15) 0.0364(15) -0.0154(15) C18B 0.091(3) 0.140(4) 0.163(4) -0.023(3) 0.074(3) -0.012(3) C19 0.0623(14) 0.0491(12) 0.0529(12) -0.0022(10) 0.0244(10) -0.0017(10) C20 0.0604(14) 0.0658(15) 0.0559(13) -0.0020(11) 0.0193(11) -0.0069(12) _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 N1 1.927(2) . ? Ni1 N3 1.932(2) . ? Ni1 N4 1.934(2) . ? Ni1 N2 1.947(2) . ? N1 C1 1.364(3) . ? N1 C4 1.366(3) . ? N2 C6 1.372(3) . ? N2 C9 1.382(3) . ? N3 C11 1.373(3) . ? N3 C14 1.380(3) . ? N4 C19 1.356(3) . ? N4 C16 1.387(3) . ? N5 C2C 1.144(5) . ? O1 C3C 1.220(4) . ? C1 C20 1.348(4) . ? C1 C2 1.527(4) . ? C2 C2C 1.494(5) . ? C2 C2A 1.518(9) . ? C2 C3 1.537(4) . ? C2 C2A' 1.556(14) . ? C2A C2B 1.537(11) . ? C2A' C2B' 1.485(17) . ? C3 C4 1.503(4) . ? C3 C3C 1.524(4) . ? C3 C3A 1.570(5) . ? C3A C3B 1.501(6) . ? C3C C3D 1.427(5) . ? C3D C3E 1.329(5) . ? C3E C5 1.460(4) . ? C4 C5 1.358(4) . ? C5 C6 1.408(4) . ? C6 C7 1.440(4) . ? C7 C8' 1.345(10) . ? C7 C8 1.361(7) . ? C7 C7A 1.508(4) . ? C7A C7B 1.489(6) . ? C8 C9 1.386(6) . ? C8 C8A 1.514(8) . ? C8A C8B 1.597(10) . ? C8' C9 1.541(11) . ? C8' C8A' 1.565(12) . ? C8A' C8B' 1.592(15) . ? C9 C10 1.364(4) . ? C10 C11 1.367(4) . ? C11 C12 1.441(4) . ? C12 C13 1.349(4) . ? C12 C12A 1.505(4) . ? C12A C12B 1.471(7) . ? C13 C14 1.436(4) . ? C13 C13A 1.498(4) . ? C13A C13B 1.520(5) . ? C14 C15 1.364(4) . ? C15 C16 1.360(4) . ? C16 C17 1.433(4) . ? C17 C18 1.352(4) . ? C17 C17A 1.502(4) . ? C17A C17B 1.486(5) . ? C18 C19 1.441(4) . ? C18 C18A 1.477(4) . ? C18A C18B 1.501(5) . ? C19 C20 1.382(4) . ? 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 N1 Ni1 N3 173.97(9) . . ? N1 Ni1 N4 90.07(9) . . ? N3 Ni1 N4 90.34(9) . . ? N1 Ni1 N2 89.48(9) . . ? N3 Ni1 N2 90.57(9) . . ? N4 Ni1 N2 175.55(9) . . ? C1 N1 C4 107.1(2) . . ? C1 N1 Ni1 127.65(17) . . ? C4 N1 Ni1 124.85(17) . . ? C6 N2 C9 104.6(2) . . ? C6 N2 Ni1 128.87(18) . . ? C9 N2 Ni1 125.82(18) . . ? C11 N3 C14 104.7(2) . . ? C11 N3 Ni1 127.97(18) . . ? C14 N3 Ni1 126.98(18) . . ? C19 N4 C16 104.2(2) . . ? C19 N4 Ni1 127.71(16) . . ? C16 N4 Ni1 128.07(18) . . ? C20 C1 N1 125.4(2) . . ? C20 C1 C2 123.6(2) . . ? N1 C1 C2 111.0(2) . . ? C2C C2 C2A 108.5(5) . . ? C2C C2 C1 107.5(3) . . ? C2A C2 C1 116.2(5) . . ? C2C C2 C3 107.3(3) . . ? C2A C2 C3 117.6(5) . . ? C1 C2 C3 98.9(2) . . ? C2C C2 C2A' 109.4(11) . . ? C2A C2 C2A' 3.1(12) . . ? C1 C2 C2A' 113.2(8) . . ? C3 C2 C2A' 119.6(11) . . ? C2 C2A C2B 114.6(8) . . ? C2B' C2A' C2 119.4(16) . . ? N5 C2C C2 178.8(4) . . ? C4 C3 C3C 113.9(3) . . ? C4 C3 C2 99.6(2) . . ? C3C C3 C2 115.7(3) . . ? C4 C3 C3A 109.2(3) . . ? C3C C3 C3A 108.5(3) . . ? C2 C3 C3A 109.5(3) . . ? C3B C3A C3 116.0(4) . . ? O1 C3C C3D 123.6(3) . . ? O1 C3C C3 120.3(3) . . ? C3D C3C C3 116.0(3) . . ? C3E C3D C3C 121.7(3) . . ? C3D C3E C5 124.4(3) . . ? C5 C4 N1 126.3(2) . . ? C5 C4 C3 123.2(2) . . ? N1 C4 C3 110.4(2) . . ? C4 C5 C6 122.2(2) . . ? C4 C5 C3E 116.0(3) . . ? C6 C5 C3E 121.8(3) . . ? N2 C6 C5 120.9(2) . . ? N2 C6 C7 110.4(2) . . ? C5 C6 C7 128.5(3) . . ? C8' C7 C8 16.4(6) . . ? C8' C7 C6 110.7(5) . . ? C8 C7 C6 104.7(3) . . ? C8' C7 C7A 119.2(5) . . ? C8 C7 C7A 127.7(4) . . ? C6 C7 C7A 127.6(3) . . ? C7B C7A C7 113.3(3) . . ? C7 C8 C9 108.5(4) . . ? C7 C8 C8A 125.6(5) . . ? C9 C8 C8A 124.5(5) . . ? C8 C8A C8B 109.4(6) . . ? C7 C8' C9 100.9(6) . . ? C7 C8' C8A' 133.4(9) . . ? C9 C8' C8A' 124.6(8) . . ? C8' C8A' C8B' 97.3(10) . . ? C10 C9 N2 123.9(3) . . ? C10 C9 C8 124.5(3) . . ? N2 C9 C8 110.7(3) . . ? C10 C9 C8' 125.9(4) . . ? N2 C9 C8' 110.1(4) . . ? C8 C9 C8' 13.9(5) . . ? C9 C10 C11 125.2(3) . . ? C10 C11 N3 123.5(2) . . ? C10 C11 C12 125.4(3) . . ? N3 C11 C12 111.1(3) . . ? C13 C12 C11 106.3(3) . . ? C13 C12 C12A 129.1(3) . . ? C11 C12 C12A 124.6(3) . . ? C12B C12A C12 113.5(4) . . ? C12 C13 C14 107.3(3) . . ? C12 C13 C13A 129.1(3) . . ? C14 C13 C13A 123.5(3) . . ? C13 C13A C13B 112.4(3) . . ? C15 C14 N3 124.2(2) . . ? C15 C14 C13 125.0(3) . . ? N3 C14 C13 110.5(2) . . ? C16 C15 C14 125.2(3) . . ? C15 C16 N4 123.5(2) . . ? C15 C16 C17 125.5(2) . . ? N4 C16 C17 110.9(2) . . ? C18 C17 C16 106.8(2) . . ? C18 C17 C17A 128.0(3) . . ? C16 C17 C17A 125.2(3) . . ? C17B C17A C17 114.2(3) . . ? C17 C18 C19 106.1(2) . . ? C17 C18 C18A 128.1(3) . . ? C19 C18 C18A 125.6(2) . . ? C18 C18A C18B 112.5(3) . . ? N4 C19 C20 124.6(2) . . ? N4 C19 C18 112.0(2) . . ? C20 C19 C18 123.3(2) . . ? C1 C20 C19 123.6(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.394 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.067 data_new11p _database_code_CSD 172741 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-amido- 2,3,7,12,13,17,18,10^3^-octaethyl-benzochlorin ; _chemical_name_common 11 _chemical_melting_point ? _chemical_formula_moiety 'C40 H49 N5 O' _chemical_formula_sum 'C40 H49 N5 O' _chemical_formula_weight 615.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 19.084(4) _cell_length_b 27.306(6) _cell_length_c 15.113(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.21(3) _cell_angle_gamma 90.00 _cell_volume 7066(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2656 _exptl_absorpt_coefficient_mu 0.543 _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 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD-4 _diffrn_measurement_method '\w/2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 12208 _diffrn_reflns_av_R_equivalents 0.0969 _diffrn_reflns_av_sigmaI/netI 0.1200 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 64.99 _reflns_number_total 6021 _reflns_number_gt 1967 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 _computing_cell_refinement 'least-squares CAD4 program' _computing_data_reduction XCAD4 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All hydrogen atoms bonded to nitrogen were found on a difference map. Peripheral amino hydrogens were refined freely while core porphyrinic hydrogens were refined with a riding model. Core hydrogen positions were found in proximity to each of the porphyrinic nitrogens; their occupancies were summed to 2.000(1) and refined as 4 free-variables with their thermal parameters refined as a single free-variable. All other hydrogen atom positions were deterimined by their idealized geomerty and refined with a riding model. Non-hydrogen atoms were refined with anisotropic thermal parameters. ; _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^)+(0.1041P)^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_number_reflns 6021 _refine_ls_number_parameters 436 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2245 _refine_ls_R_factor_gt 0.0717 _refine_ls_wR_factor_ref 0.2428 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 N1 N 0.3438(2) 0.16098(14) 0.3671(3) 0.0761(11) Uani 1 1 d . . . H1 H 0.3451 0.1919 0.3787 0.097(18) Uiso 0.25(3) 1 calc PR . . N2 N 0.3536(2) 0.21867(15) 0.5278(3) 0.0766(11) Uani 1 1 d . . . H2 H 0.3555 0.2214 0.4723 0.097(18) Uiso 0.76(6) 1 calc PR . . N3 N 0.3541(2) 0.30741(17) 0.4029(3) 0.0813(11) Uani 1 1 d . . . H3 H 0.3542 0.2765 0.3923 0.097(18) Uiso 0.40(6) 1 calc PR . . N4 N 0.3478(2) 0.24853(15) 0.2480(3) 0.0771(11) Uani 1 1 d . . . H4 H 0.3465 0.2448 0.3038 0.097(18) Uiso 0.59(6) 1 calc PR . . N5 N 0.4734(4) 0.0625(2) 0.3532(4) 0.1112(17) Uani 1 1 d . . . H5 H 0.484(3) 0.0754(18) 0.415(4) 0.12(2) Uiso 1 1 d . . . H6 H 0.509(4) 0.048(2) 0.335(4) 0.15(3) Uiso 1 1 d . . . O1 O 0.3951(2) 0.05146(14) 0.1924(3) 0.1104(12) Uani 1 1 d . . . C1 C 0.3398(3) 0.13955(18) 0.2849(3) 0.0740(13) Uani 1 1 d . . . C2 C 0.3337(3) 0.08473(18) 0.2875(3) 0.0735(13) Uani 1 1 d . . . C2A C 0.2564(3) 0.06641(18) 0.2031(4) 0.0907(15) Uani 1 1 d . . . H2A1 H 0.2552 0.0758 0.1406 0.109 Uiso 1 1 calc R . . H2A2 H 0.2555 0.0309 0.2052 0.109 Uiso 1 1 calc R . . C2B C 0.1827(3) 0.0860(2) 0.2070(4) 0.1165(19) Uani 1 1 d . . . H2B1 H 0.1777 0.0716 0.2619 0.175 Uiso 1 1 calc R . . H2B2 H 0.1378 0.0778 0.1470 0.175 Uiso 1 1 calc R . . H2B3 H 0.1864 0.1210 0.2146 0.175 Uiso 1 1 calc R . . C2C C 0.4046(4) 0.06289(18) 0.2745(5) 0.0865(15) Uani 1 1 d . . . C3 C 0.3419(3) 0.07701(18) 0.3907(3) 0.0766(13) Uani 1 1 d . . . C3A C 0.3472(3) 0.03500(19) 0.4411(4) 0.0888(15) Uani 1 1 d . . . C3B C 0.3462(4) -0.0147(2) 0.4026(4) 0.118(2) Uani 1 1 d . . . H3B1 H 0.3252 -0.0126 0.3314 0.142 Uiso 1 1 calc R . . H3B2 H 0.3999 -0.0258 0.4274 0.142 Uiso 1 1 calc R . . C3C C 0.3021(4) -0.0524(2) 0.4257(4) 0.148(3) Uani 1 1 d . . . H3C1 H 0.3238 -0.0566 0.4959 0.222 Uiso 1 1 calc R . . H3C2 H 0.3051 -0.0828 0.3957 0.222 Uiso 1 1 calc R . . H3C3 H 0.2485 -0.0425 0.4007 0.222 Uiso 1 1 calc R . . C3D C 0.3569(3) 0.0411(2) 0.5391(4) 0.1006(17) Uani 1 1 d . . . H3D H 0.3622 0.0137 0.5781 0.121 Uiso 1 1 calc R . . C3E C 0.3586(3) 0.0861(2) 0.5763(4) 0.0927(16) Uani 1 1 d . . . H3E H 0.3644 0.0879 0.6406 0.111 Uiso 1 1 calc R . . C4 C 0.3456(3) 0.12308(18) 0.4296(3) 0.0738(13) Uani 1 1 d . . . C5 C 0.3525(3) 0.13010(19) 0.5279(3) 0.0758(13) Uani 1 1 d . . . C6 C 0.3525(3) 0.1756(2) 0.5698(4) 0.0773(13) Uani 1 1 d . . . C7 C 0.3515(3) 0.1882(2) 0.6632(3) 0.0800(14) Uani 1 1 d . . . C7A C 0.3496(3) 0.1535(2) 0.7396(4) 0.0962(16) Uani 1 1 d . . . H7A1 H 0.3180 0.1253 0.7065 0.115 Uiso 1 1 calc R . . H7A2 H 0.3248 0.1698 0.7754 0.115 Uiso 1 1 calc R . . C7B C 0.4311(3) 0.1358(2) 0.8136(4) 0.119(2) Uani 1 1 d . . . H7B1 H 0.4544 0.1173 0.7794 0.179 Uiso 1 1 calc R . . H7B2 H 0.4264 0.1155 0.8625 0.179 Uiso 1 1 calc R . . H7B3 H 0.4634 0.1636 0.8451 0.179 Uiso 1 1 calc R . . C8 C 0.3507(3) 0.2373(2) 0.6689(3) 0.0796(14) Uani 1 1 d . . . C8A C 0.3491(3) 0.2670(2) 0.7508(4) 0.1002(17) Uani 1 1 d . . . H8A1 H 0.3250 0.2481 0.7842 0.120 Uiso 1 1 calc R . . H8A2 H 0.3174 0.2960 0.7235 0.120 Uiso 1 1 calc R . . C8B C 0.4300(4) 0.2826(2) 0.8251(4) 0.127(2) Uani 1 1 d . . . H8B1 H 0.4625 0.2541 0.8497 0.190 Uiso 1 1 calc R . . H8B2 H 0.4266 0.2994 0.8788 0.190 Uiso 1 1 calc R . . H8B3 H 0.4523 0.3040 0.7938 0.190 Uiso 1 1 calc R . . C9 C 0.3512(3) 0.2576(2) 0.5825(4) 0.0761(13) Uani 1 1 d . . . C10 C 0.3511(3) 0.3062(2) 0.5625(4) 0.0865(15) Uani 1 1 d . . . H10 H 0.3491 0.3267 0.6104 0.104 Uiso 1 1 calc R . . C11 C 0.3535(3) 0.33027(19) 0.4836(4) 0.0822(14) Uani 1 1 d . . . C12 C 0.3542(3) 0.38214(19) 0.4738(4) 0.0897(15) Uani 1 1 d . . . C12A C 0.3541(4) 0.4193(2) 0.5470(4) 0.118(2) Uani 1 1 d . . . H12A H 0.3311 0.4495 0.5129 0.141 Uiso 1 1 calc R . . H12B H 0.3221 0.4074 0.5776 0.141 Uiso 1 1 calc R . . C12B C 0.4336(5) 0.4292(3) 0.6240(6) 0.188(4) Uani 1 1 d . . . H12C H 0.4530 0.4009 0.6654 0.282 Uiso 1 1 calc R . . H12D H 0.4323 0.4566 0.6631 0.282 Uiso 1 1 calc R . . H12E H 0.4672 0.4366 0.5937 0.282 Uiso 1 1 calc R . . C13 C 0.3554(3) 0.3913(2) 0.3850(4) 0.0941(15) Uani 1 1 d . . . C13A C 0.3581(4) 0.4398(2) 0.3428(5) 0.129(2) Uani 1 1 d . . . H13A H 0.3404 0.4645 0.3746 0.154 Uiso 1 1 calc R . . H13B H 0.3220 0.4398 0.2732 0.154 Uiso 1 1 calc R . . C13B C 0.4384(5) 0.4541(2) 0.3543(6) 0.174(3) Uani 1 1 d . . . H13C H 0.4734 0.4575 0.4230 0.261 Uiso 1 1 calc R . . H13D H 0.4351 0.4846 0.3212 0.261 Uiso 1 1 calc R . . H13E H 0.4576 0.4291 0.3258 0.261 Uiso 1 1 calc R . . C14 C 0.3546(3) 0.3440(2) 0.3448(4) 0.0835(14) Uani 1 1 d . . . C15 C 0.3526(3) 0.3366(2) 0.2498(4) 0.0917(15) Uani 1 1 d . . . H15 H 0.3525 0.3643 0.2139 0.110 Uiso 1 1 calc R . . C16 C 0.3509(3) 0.2928(2) 0.2088(4) 0.0816(14) Uani 1 1 d . . . C17 C 0.3529(3) 0.2822(2) 0.1151(3) 0.0842(14) Uani 1 1 d . . . C17A C 0.3561(4) 0.3220(2) 0.0465(4) 0.1124(19) Uani 1 1 d . . . H17A H 0.3345 0.3096 -0.0204 0.135 Uiso 1 1 calc R . . H17B H 0.3248 0.3497 0.0477 0.135 Uiso 1 1 calc R . . C17B C 0.4376(4) 0.3380(3) 0.0773(5) 0.146(3) Uani 1 1 d . . . H17C H 0.4592 0.3497 0.1440 0.219 Uiso 1 1 calc R . . H17D H 0.4385 0.3638 0.0347 0.219 Uiso 1 1 calc R . . H17E H 0.4680 0.3108 0.0733 0.219 Uiso 1 1 calc R . . C18 C 0.3527(3) 0.2336(2) 0.1053(3) 0.0795(14) Uani 1 1 d . . . C18A C 0.3625(3) 0.20513(19) 0.0269(3) 0.0955(16) Uani 1 1 d . . . H18A H 0.3451 0.2248 -0.0324 0.115 Uiso 1 1 calc R . . H18B H 0.3304 0.1759 0.0114 0.115 Uiso 1 1 calc R . . C18B C 0.4487(4) 0.1904(2) 0.0612(4) 0.135(2) Uani 1 1 d . . . H18C H 0.4804 0.2194 0.0754 0.202 Uiso 1 1 calc R . . H18D H 0.4536 0.1721 0.0099 0.202 Uiso 1 1 calc R . . H18E H 0.4658 0.1706 0.1195 0.202 Uiso 1 1 calc R . . C19 C 0.3469(3) 0.2114(2) 0.1894(3) 0.0759(13) Uani 1 1 d . . . C20 C 0.3420(3) 0.16354(18) 0.2038(3) 0.0775(13) Uani 1 1 d . . . H20 H 0.3397 0.1432 0.1532 0.093 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.073(3) 0.089(3) 0.069(2) -0.009(2) 0.034(2) -0.007(2) N2 0.076(3) 0.085(3) 0.074(3) -0.006(2) 0.038(2) -0.004(2) N3 0.084(3) 0.079(3) 0.084(3) -0.001(3) 0.040(2) 0.004(2) N4 0.088(3) 0.076(3) 0.073(3) -0.006(2) 0.040(2) -0.007(2) N5 0.093(4) 0.161(5) 0.084(4) -0.007(3) 0.042(4) 0.013(4) O1 0.100(3) 0.145(3) 0.100(3) -0.038(2) 0.058(2) -0.016(2) C1 0.075(3) 0.085(3) 0.061(3) -0.007(3) 0.029(3) -0.006(3) C2 0.075(3) 0.087(4) 0.061(3) -0.011(3) 0.032(3) -0.007(3) C2A 0.092(4) 0.100(4) 0.084(3) -0.006(3) 0.042(3) -0.009(3) C2B 0.082(4) 0.166(6) 0.101(4) -0.021(4) 0.039(3) -0.004(4) C2C 0.094(5) 0.095(4) 0.080(4) -0.011(3) 0.047(4) -0.003(3) C3 0.084(4) 0.074(3) 0.080(3) -0.005(3) 0.044(3) -0.008(3) C3A 0.108(4) 0.078(4) 0.091(4) 0.002(3) 0.054(3) -0.002(3) C3B 0.159(6) 0.087(4) 0.120(5) 0.009(4) 0.073(5) 0.001(4) C3C 0.203(7) 0.125(5) 0.109(5) -0.006(4) 0.063(5) -0.048(5) C3D 0.126(5) 0.098(4) 0.082(4) 0.017(3) 0.049(4) 0.009(4) C3E 0.112(5) 0.095(4) 0.079(3) 0.009(3) 0.050(3) 0.011(3) C4 0.068(3) 0.084(4) 0.071(3) 0.013(3) 0.032(3) 0.005(3) C5 0.075(3) 0.090(4) 0.062(3) 0.008(3) 0.030(3) 0.002(3) C6 0.071(4) 0.090(4) 0.071(3) -0.002(3) 0.032(3) -0.001(3) C7 0.072(4) 0.108(4) 0.061(3) -0.004(3) 0.030(3) -0.004(3) C7A 0.088(4) 0.129(5) 0.080(3) 0.008(3) 0.044(3) 0.007(3) C7B 0.109(5) 0.173(6) 0.071(3) 0.018(4) 0.036(4) 0.012(4) C8 0.077(4) 0.105(4) 0.061(3) -0.006(3) 0.034(3) -0.005(3) C8A 0.102(5) 0.138(5) 0.071(3) -0.019(3) 0.048(3) -0.007(4) C8B 0.115(5) 0.178(6) 0.088(4) -0.041(4) 0.045(4) -0.021(4) C9 0.071(4) 0.085(4) 0.074(3) -0.016(3) 0.032(3) -0.004(3) C10 0.086(4) 0.101(4) 0.083(4) -0.016(3) 0.047(3) -0.005(3) C11 0.082(4) 0.086(4) 0.082(3) -0.021(3) 0.040(3) 0.000(3) C12 0.095(4) 0.081(4) 0.095(4) -0.016(3) 0.044(3) 0.003(3) C12A 0.130(6) 0.113(5) 0.115(5) -0.018(4) 0.059(5) -0.008(4) C12B 0.160(8) 0.235(9) 0.171(7) -0.099(7) 0.075(7) -0.064(7) C13 0.097(4) 0.081(4) 0.104(4) 0.002(4) 0.045(3) 0.007(3) C13A 0.166(7) 0.106(5) 0.112(5) 0.000(4) 0.060(5) 0.013(5) C13B 0.192(9) 0.118(5) 0.230(9) 0.022(6) 0.110(8) -0.026(5) C14 0.090(4) 0.071(3) 0.089(4) 0.004(3) 0.038(3) 0.007(3) C15 0.108(4) 0.091(4) 0.084(4) 0.008(3) 0.050(3) 0.002(3) C16 0.082(4) 0.085(4) 0.079(3) -0.003(3) 0.036(3) -0.001(3) C17 0.092(4) 0.092(4) 0.074(3) 0.013(3) 0.042(3) -0.002(3) C17A 0.120(5) 0.134(5) 0.095(4) -0.001(4) 0.058(4) -0.020(4) C17B 0.142(6) 0.193(7) 0.107(5) -0.001(5) 0.058(4) -0.048(5) C18 0.083(4) 0.098(4) 0.058(3) 0.006(3) 0.033(3) -0.001(3) C18A 0.124(5) 0.108(4) 0.066(3) -0.001(3) 0.052(3) -0.004(3) C18B 0.131(6) 0.184(6) 0.111(4) -0.010(4) 0.073(5) 0.023(5) C19 0.078(4) 0.080(3) 0.070(3) -0.002(3) 0.033(3) -0.003(3) C20 0.087(4) 0.085(4) 0.067(3) -0.003(3) 0.040(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.345(5) . ? N1 C4 1.392(5) . ? N2 C6 1.339(6) . ? N2 C9 1.360(5) . ? N3 C14 1.333(5) . ? N3 C11 1.375(5) . ? N4 C19 1.341(5) . ? N4 C16 1.358(6) . ? N5 C2C 1.326(7) . ? O1 C2C 1.213(5) . ? C1 C20 1.406(6) . ? C1 C2 1.503(6) . ? C2 C3 1.511(6) . ? C2 C2A 1.547(6) . ? C2 C2C 1.568(6) . ? C2A C2B 1.529(6) . ? C3 C3A 1.356(6) . ? C3 C4 1.378(6) . ? C3A C3D 1.419(7) . ? C3A C3B 1.474(7) . ? C3B C3C 1.466(7) . ? C3D C3E 1.347(7) . ? C3E C5 1.383(6) . ? C4 C5 1.445(6) . ? C5 C6 1.395(6) . ? C6 C7 1.461(6) . ? C7 C8 1.344(6) . ? C7 C7A 1.506(6) . ? C7A C7B 1.538(7) . ? C8 C9 1.424(6) . ? C8 C8A 1.491(6) . ? C8A C8B 1.514(7) . ? C9 C10 1.359(7) . ? C10 C11 1.380(7) . ? C11 C12 1.425(7) . ? C12 C13 1.375(7) . ? C12 C12A 1.502(7) . ? C12A C12B 1.472(8) . ? C13 C14 1.423(6) . ? C13 C13A 1.482(7) . ? C13A C13B 1.515(8) . ? C14 C15 1.434(6) . ? C15 C16 1.343(6) . ? C16 C17 1.461(6) . ? C17 C18 1.336(6) . ? C17 C17A 1.521(7) . ? C17A C17B 1.479(7) . ? C18 C19 1.456(6) . ? C18 C18A 1.495(6) . ? C18A C18B 1.544(7) . ? C19 C20 1.336(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 C1 N1 C4 106.2(4) . . ? C6 N2 C9 112.8(4) . . ? C14 N3 C11 104.4(4) . . ? C19 N4 C16 111.9(4) . . ? N1 C1 C20 126.2(5) . . ? N1 C1 C2 112.5(4) . . ? C20 C1 C2 121.3(4) . . ? C1 C2 C3 101.1(4) . . ? C1 C2 C2A 111.0(4) . . ? C3 C2 C2A 115.6(4) . . ? C1 C2 C2C 107.1(4) . . ? C3 C2 C2C 112.0(4) . . ? C2A C2 C2C 109.6(4) . . ? C2B C2A C2 114.4(4) . . ? O1 C2C N5 123.9(5) . . ? O1 C2C C2 118.6(5) . . ? N5 C2C C2 117.2(5) . . ? C3A C3 C4 123.7(4) . . ? C3A C3 C2 130.2(5) . . ? C4 C3 C2 106.0(4) . . ? C3 C3A C3D 115.5(5) . . ? C3 C3A C3B 124.9(5) . . ? C3D C3A C3B 119.5(5) . . ? C3C C3B C3A 117.4(5) . . ? C3E C3D C3A 120.7(5) . . ? C3D C3E C5 126.3(5) . . ? C3 C4 N1 114.0(4) . . ? C3 C4 C5 121.7(4) . . ? N1 C4 C5 124.3(4) . . ? C3E C5 C6 123.5(5) . . ? C3E C5 C4 112.1(4) . . ? C6 C5 C4 124.5(5) . . ? N2 C6 C5 124.4(4) . . ? N2 C6 C7 105.1(5) . . ? C5 C6 C7 130.5(5) . . ? C8 C7 C6 107.6(4) . . ? C8 C7 C7A 124.9(5) . . ? C6 C7 C7A 127.5(5) . . ? C7 C7A C7B 113.4(4) . . ? C7 C8 C9 109.0(4) . . ? C7 C8 C8A 127.1(5) . . ? C9 C8 C8A 124.0(5) . . ? C8 C8A C8B 112.3(4) . . ? C10 C9 N2 128.6(5) . . ? C10 C9 C8 125.8(5) . . ? N2 C9 C8 105.5(5) . . ? C9 C10 C11 131.3(5) . . ? N3 C11 C10 124.5(5) . . ? N3 C11 C12 110.8(5) . . ? C10 C11 C12 124.7(5) . . ? C13 C12 C11 106.6(5) . . ? C13 C12 C12A 127.1(5) . . ? C11 C12 C12A 126.3(5) . . ? C12B C12A C12 111.7(5) . . ? C12 C13 C14 104.5(5) . . ? C12 C13 C13A 126.9(5) . . ? C14 C13 C13A 128.6(5) . . ? C13 C13A C13B 114.0(6) . . ? N3 C14 C13 113.6(5) . . ? N3 C14 C15 123.3(5) . . ? C13 C14 C15 123.1(5) . . ? C16 C15 C14 124.9(5) . . ? C15 C16 N4 126.0(5) . . ? C15 C16 C17 128.1(5) . . ? N4 C16 C17 105.8(4) . . ? C18 C17 C16 107.7(4) . . ? C18 C17 C17A 129.3(5) . . ? C16 C17 C17A 123.0(5) . . ? C17B C17A C17 110.5(5) . . ? C17 C18 C19 108.2(4) . . ? C17 C18 C18A 127.6(4) . . ? C19 C18 C18A 124.1(5) . . ? C18 C18A C18B 110.9(4) . . ? C20 C19 N4 127.8(4) . . ? C20 C19 C18 125.9(5) . . ? N4 C19 C18 106.2(4) . . ? C19 C20 C1 129.0(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 64.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.198 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.052