# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Christian Bruckner' 'Jeanette A Krause' 'Lalith P. Samankumara' 'Matthias Zeller' _publ_contact_author_name 'Christian Bruckner' _publ_contact_author_email C.BRUCKNER@UCONN.EDU _publ_section_title ; Syntheses, Structures, Modification, and Optical Properties of meso-Tetraaryl-2,3-dimethoxychlorin, and Two Isomeric meso-Tetraaryl-2,3,12,13-tetrahydroxybacteriochlorins ; # Attachment 'X-ray_Structures_Chlorins.cif' data_4b _database_code_depnum_ccdc_archive 'CCDC 756648' #TrackingRef 'X-ray_Structures_Chlorins.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H58 N4 O4, 4(C H4 O)' _chemical_formula_sum 'C60 H74 N4 O8' _chemical_formula_weight 979.23 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1709(10) _cell_length_b 11.1196(14) _cell_length_c 15.653(2) _cell_angle_alpha 76.5000(17) _cell_angle_beta 84.6620(19) _cell_angle_gamma 79.0700(18) _cell_volume 1356.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3197 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 31.15 _exptl_crystal_description rod _exptl_crystal_colour black _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2007)' _exptl_special_details ; The crystal used was found to be consisting of two independent crystallites. The orientation matrices for the two components were identified using the program Cell_Now, and the two components were integrated using Saint. The data were corrected for absorption using twinabs, and the structure was solved and refined using direct methods with only the non-overlapping reflections of component below a d-spacing threshold of 0.75. The Rint value given is for all reflections before the cutoff at d = 0.75 and is based on agreement between observed single and composite intensities and those calculated from refined unique intensities and twin fractions (TWINABS (Sheldrick, 2007)). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6634 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6634 _reflns_number_gt 5216 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4' _computing_data_reduction 'Apex2 v2008.2-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0614P)^2^+0.3388P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6634 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C1 C -0.23361(16) 0.58497(12) 0.84751(8) 0.0181(3) Uani 1 1 d . . . C2 C -0.26923(17) 0.68575(12) 0.77351(9) 0.0218(3) Uani 1 1 d . . . H2 H -0.3546 0.6954 0.7340 0.026 Uiso 1 1 calc R . . C3 C -0.16012(17) 0.76652(12) 0.76870(9) 0.0219(3) Uani 1 1 d . . . H3 H -0.1561 0.8414 0.7250 0.026 Uiso 1 1 calc R . . C4 C -0.05346(16) 0.71944(12) 0.84034(8) 0.0182(3) Uani 1 1 d . . . C5 C 0.08211(16) 0.77195(11) 0.85534(8) 0.0176(2) Uani 1 1 d . . . C6 C 0.18306(15) 0.72924(11) 0.92688(8) 0.0172(2) Uani 1 1 d . . . C7 C 0.32741(16) 0.79122(12) 0.94059(9) 0.0192(3) Uani 1 1 d . . . H7 H 0.4287 0.7597 0.9058 0.023 Uiso 1 1 calc R . . C8 C 0.35393(16) 0.73781(12) 1.03904(9) 0.0198(3) Uani 1 1 d . . . H8 H 0.4755 0.7171 1.0506 0.024 Uiso 1 1 calc R . . C9 C 0.27871(15) 0.61899(12) 1.05428(8) 0.0173(2) Uani 1 1 d . . . C10 C 0.30981(15) 0.52262(12) 1.12826(8) 0.0180(3) Uani 1 1 d . . . C11 C 0.12241(16) 0.87734(12) 0.78182(8) 0.0179(2) Uani 1 1 d . . . C12 C 0.02568(17) 0.99645(12) 0.76846(9) 0.0216(3) Uani 1 1 d . . . H12 H -0.0629 1.0152 0.8097 0.026 Uiso 1 1 calc R . . C13 C 0.05782(17) 1.08848(12) 0.69492(9) 0.0220(3) Uani 1 1 d . . . H13 H -0.0093 1.1696 0.6867 0.026 Uiso 1 1 calc R . . C14 C 0.18641(16) 1.06398(12) 0.63315(8) 0.0199(3) Uani 1 1 d . . . C15 C 0.28358(17) 0.94484(13) 0.64762(9) 0.0228(3) Uani 1 1 d . . . H15 H 0.3729 0.9263 0.6067 0.027 Uiso 1 1 calc R . . C16 C 0.25250(16) 0.85250(12) 0.72073(9) 0.0208(3) Uani 1 1 d . . . H16 H 0.3204 0.7717 0.7292 0.025 Uiso 1 1 calc R . . C17 C 0.21698(18) 1.16346(13) 0.55134(9) 0.0244(3) Uani 1 1 d . . . H17 H 0.1360 1.2419 0.5553 0.029 Uiso 1 1 calc R . . C18 C 0.1842(2) 1.12486(16) 0.46795(10) 0.0363(4) Uani 1 1 d . . . H18A H 0.2644 1.0497 0.4612 0.055 Uiso 1 1 calc R . . H18B H 0.1965 1.1934 0.4169 0.055 Uiso 1 1 calc R . . H18C H 0.0706 1.1067 0.4723 0.055 Uiso 1 1 calc R . . C19 C 0.39319(19) 1.19449(15) 0.54534(10) 0.0323(3) Uani 1 1 d . . . H19A H 0.4090 1.2261 0.5969 0.049 Uiso 1 1 calc R . . H19B H 0.4076 1.2587 0.4918 0.049 Uiso 1 1 calc R . . H19C H 0.4756 1.1185 0.5435 0.049 Uiso 1 1 calc R . . C20 C 0.43164(16) 0.53012(12) 1.19230(8) 0.0181(3) Uani 1 1 d . . . C21 C 0.60308(16) 0.51005(12) 1.17270(9) 0.0204(3) Uani 1 1 d . . . H21 H 0.6441 0.5012 1.1153 0.024 Uiso 1 1 calc R . . C22 C 0.71491(16) 0.50276(12) 1.23627(9) 0.0210(3) Uani 1 1 d . . . H22 H 0.8314 0.4894 1.2215 0.025 Uiso 1 1 calc R . . C23 C 0.65923(16) 0.51469(12) 1.32110(8) 0.0196(3) Uani 1 1 d . . . C24 C 0.48787(17) 0.54085(14) 1.33902(9) 0.0242(3) Uani 1 1 d . . . H24 H 0.4468 0.5534 1.3956 0.029 Uiso 1 1 calc R . . C25 C 0.37589(17) 0.54890(14) 1.27563(9) 0.0236(3) Uani 1 1 d . . . H25 H 0.2594 0.5675 1.2894 0.028 Uiso 1 1 calc R . . C26 C 0.77681(16) 0.49191(13) 1.39537(9) 0.0230(3) Uani 1 1 d . . . H26 H 0.7275 0.5489 1.4355 0.028 Uiso 1 1 calc R . . C27 C 0.7872(2) 0.35675(15) 1.44827(11) 0.0338(3) Uani 1 1 d . . . H27A H 0.6747 0.3408 1.4689 0.051 Uiso 1 1 calc R . . H27B H 0.8555 0.3440 1.4990 0.051 Uiso 1 1 calc R . . H27C H 0.8381 0.2988 1.4109 0.051 Uiso 1 1 calc R . . C28 C 0.95090(18) 0.51970(16) 1.36397(11) 0.0329(3) Uani 1 1 d . . . H28A H 1.0071 0.4588 1.3299 0.049 Uiso 1 1 calc R . . H28B H 1.0156 0.5135 1.4150 0.049 Uiso 1 1 calc R . . H28C H 0.9418 0.6047 1.3269 0.049 Uiso 1 1 calc R . . C29 C 0.4548(2) 0.91434(17) 0.22911(10) 0.0366(4) Uani 1 1 d . . . H29A H 0.5451 0.9427 0.2519 0.055 Uiso 1 1 calc R . . H29B H 0.4846 0.8241 0.2314 0.055 Uiso 1 1 calc R . . H29C H 0.3518 0.9307 0.2651 0.055 Uiso 1 1 calc R . . C30 C 0.8378(3) 0.79098(18) 0.08153(19) 0.0692(8) Uani 1 1 d . . . H30A H 0.7901 0.7963 0.1406 0.104 Uiso 1 1 calc R . . H30B H 0.9021 0.7066 0.0831 0.104 Uiso 1 1 calc R . . H30C H 0.7477 0.8077 0.0409 0.104 Uiso 1 1 calc R . . N1 N 0.17079(13) 0.62567(10) 0.99156(7) 0.0169(2) Uani 1 1 d . . . N2 N -0.10464(13) 0.61079(10) 0.88767(7) 0.0176(2) Uani 1 1 d . . . H2B H -0.0613 0.5644 0.9366 0.021 Uiso 1 1 calc R . . O1 O 0.29499(12) 0.92323(8) 0.91734(6) 0.0230(2) Uani 1 1 d . . . H1 H 0.3852 0.9501 0.9026 0.034 Uiso 1 1 calc R . . O2 O 0.26613(13) 0.81840(9) 1.09325(6) 0.0256(2) Uani 1 1 d . . . H2A H 0.1655 0.8382 1.0806 0.038 Uiso 1 1 calc R . . O3 O 0.42987(13) 0.98030(10) 0.14068(7) 0.0309(2) Uani 1 1 d . . . H3A H 0.3789 0.9404 0.1157 0.046 Uiso 1 1 calc R . . O4 O 0.94342(13) 0.88024(10) 0.05273(8) 0.0341(3) Uani 1 1 d . . . H4 H 0.8904 0.9518 0.0556 0.051 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 C1 0.0195(6) 0.0192(6) 0.0161(6) -0.0031(5) -0.0027(5) -0.0052(5) C2 0.0251(7) 0.0214(6) 0.0197(6) -0.0005(5) -0.0071(5) -0.0077(5) C3 0.0281(7) 0.0195(6) 0.0182(6) 0.0005(5) -0.0057(5) -0.0083(5) C4 0.0225(6) 0.0168(6) 0.0157(6) -0.0022(5) -0.0013(5) -0.0058(5) C5 0.0213(6) 0.0157(6) 0.0164(6) -0.0029(5) 0.0003(5) -0.0059(5) C6 0.0190(6) 0.0157(6) 0.0178(6) -0.0042(5) 0.0004(5) -0.0057(5) C7 0.0188(6) 0.0169(6) 0.0222(6) -0.0018(5) -0.0018(5) -0.0067(5) C8 0.0191(6) 0.0182(6) 0.0232(6) -0.0025(5) -0.0040(5) -0.0075(5) C9 0.0173(6) 0.0172(6) 0.0188(6) -0.0049(5) -0.0003(4) -0.0057(5) C10 0.0178(6) 0.0200(6) 0.0177(6) -0.0044(5) -0.0025(5) -0.0056(5) C11 0.0212(6) 0.0175(6) 0.0166(6) -0.0016(5) -0.0034(5) -0.0086(5) C12 0.0240(7) 0.0193(6) 0.0212(6) -0.0032(5) 0.0015(5) -0.0057(5) C13 0.0240(7) 0.0162(6) 0.0247(7) -0.0024(5) -0.0011(5) -0.0032(5) C14 0.0222(7) 0.0195(6) 0.0181(6) -0.0003(5) -0.0025(5) -0.0078(5) C15 0.0240(7) 0.0228(7) 0.0201(6) -0.0028(5) 0.0024(5) -0.0048(5) C16 0.0222(7) 0.0171(6) 0.0219(6) -0.0017(5) -0.0020(5) -0.0030(5) C17 0.0295(7) 0.0201(6) 0.0205(6) 0.0026(5) -0.0011(5) -0.0055(5) C18 0.0511(10) 0.0329(8) 0.0224(7) 0.0021(6) -0.0073(7) -0.0084(7) C19 0.0335(8) 0.0273(7) 0.0329(8) 0.0041(6) 0.0019(6) -0.0120(6) C20 0.0206(6) 0.0153(6) 0.0185(6) -0.0009(5) -0.0035(5) -0.0060(5) C21 0.0222(6) 0.0201(6) 0.0190(6) -0.0046(5) -0.0001(5) -0.0040(5) C22 0.0162(6) 0.0217(6) 0.0250(7) -0.0056(5) -0.0009(5) -0.0023(5) C23 0.0204(6) 0.0179(6) 0.0219(6) -0.0039(5) -0.0045(5) -0.0058(5) C24 0.0222(7) 0.0338(8) 0.0195(6) -0.0092(6) -0.0005(5) -0.0081(5) C25 0.0160(6) 0.0328(7) 0.0242(7) -0.0078(6) -0.0009(5) -0.0077(5) C26 0.0200(7) 0.0281(7) 0.0233(7) -0.0083(6) -0.0044(5) -0.0054(5) C27 0.0337(8) 0.0352(8) 0.0320(8) 0.0003(7) -0.0147(6) -0.0077(6) C28 0.0231(7) 0.0455(9) 0.0349(8) -0.0110(7) -0.0054(6) -0.0129(6) C29 0.0360(9) 0.0462(10) 0.0307(8) -0.0051(7) -0.0041(6) -0.0179(7) C30 0.0466(12) 0.0348(10) 0.131(2) -0.0360(12) 0.0423(13) -0.0211(9) N1 0.0191(5) 0.0163(5) 0.0161(5) -0.0033(4) -0.0007(4) -0.0054(4) N2 0.0205(5) 0.0173(5) 0.0157(5) -0.0008(4) -0.0040(4) -0.0069(4) O1 0.0244(5) 0.0165(4) 0.0281(5) 0.0004(4) -0.0037(4) -0.0091(4) O2 0.0316(5) 0.0234(5) 0.0255(5) -0.0084(4) -0.0044(4) -0.0086(4) O3 0.0327(6) 0.0327(6) 0.0316(6) -0.0056(5) -0.0041(4) -0.0170(4) O4 0.0300(6) 0.0277(6) 0.0482(7) -0.0147(5) 0.0058(5) -0.0098(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 C1 N2 1.3821(16) . ? C1 C10 1.4105(17) 2_567 ? C1 C2 1.4197(18) . ? C2 C3 1.3663(18) . ? C2 H2 0.9500 . ? C3 C4 1.4233(18) . ? C3 H3 0.9500 . ? C4 N2 1.3782(16) . ? C4 C5 1.4075(17) . ? C5 C6 1.3911(18) . ? C5 C11 1.5007(17) . ? C6 N1 1.3571(16) . ? C6 C7 1.5286(17) . ? C7 O1 1.4065(15) . ? C7 C8 1.5365(18) . ? C7 H7 1.0000 . ? C8 O2 1.4269(16) . ? C8 C9 1.5211(17) . ? C8 H8 1.0000 . ? C9 N1 1.3599(16) . ? C9 C10 1.3877(18) . ? C10 C1 1.4105(17) 2_567 ? C10 C20 1.5030(17) . ? C11 C12 1.3882(18) . ? C11 C16 1.3941(18) . ? C12 C13 1.3917(18) . ? C12 H12 0.9500 . ? C13 C14 1.3923(19) . ? C13 H13 0.9500 . ? C14 C15 1.3897(19) . ? C14 C17 1.5197(18) . ? C15 C16 1.3874(18) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.526(2) . ? C17 C19 1.533(2) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.3904(18) . ? C20 C21 1.3927(18) . ? C21 C22 1.3911(18) . ? C21 H21 0.9500 . ? C22 C23 1.3909(18) . ? C22 H22 0.9500 . ? C23 C24 1.3908(19) . ? C23 C26 1.5221(17) . ? C24 C25 1.3879(18) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C28 1.5252(19) . ? C26 C27 1.528(2) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 O3 1.4202(19) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 O4 1.406(2) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? N2 H2B 0.8800 . ? O1 H1 0.8400 . ? O2 H2A 0.8400 . ? O3 H3A 0.8400 . ? O4 H4 0.8400 . ? 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 N2 C1 C10 127.38(11) . 2_567 ? N2 C1 C2 106.24(11) . . ? C10 C1 C2 126.31(11) 2_567 . ? C3 C2 C1 108.56(11) . . ? C3 C2 H2 125.7 . . ? C1 C2 H2 125.7 . . ? C2 C3 C4 108.39(11) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? N2 C4 C5 127.94(11) . . ? N2 C4 C3 106.29(11) . . ? C5 C4 C3 125.68(12) . . ? C6 C5 C4 126.01(12) . . ? C6 C5 C11 119.89(11) . . ? C4 C5 C11 113.95(11) . . ? N1 C6 C5 124.93(11) . . ? N1 C6 C7 111.23(11) . . ? C5 C6 C7 123.80(11) . . ? O1 C7 C6 114.30(10) . . ? O1 C7 C8 113.64(10) . . ? C6 C7 C8 101.39(10) . . ? O1 C7 H7 109.1 . . ? C6 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? O2 C8 C9 109.98(10) . . ? O2 C8 C7 113.00(11) . . ? C9 C8 C7 100.91(10) . . ? O2 C8 H8 110.9 . . ? C9 C8 H8 110.9 . . ? C7 C8 H8 110.9 . . ? N1 C9 C10 126.04(11) . . ? N1 C9 C8 111.72(11) . . ? C10 C9 C8 122.03(11) . . ? C9 C10 C1 126.18(11) . 2_567 ? C9 C10 C20 119.56(11) . . ? C1 C10 C20 114.25(11) 2_567 . ? C12 C11 C16 118.73(12) . . ? C12 C11 C5 122.03(12) . . ? C16 C11 C5 119.03(11) . . ? C11 C12 C13 120.31(12) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 121.29(12) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 117.94(12) . . ? C15 C14 C17 121.01(12) . . ? C13 C14 C17 121.03(12) . . ? C16 C15 C14 121.17(12) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 120.55(12) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C14 C17 C18 111.39(12) . . ? C14 C17 C19 112.16(11) . . ? C18 C17 C19 110.37(13) . . ? C14 C17 H17 107.6 . . ? C18 C17 H17 107.6 . . ? C19 C17 H17 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 118.04(12) . . ? C25 C20 C10 120.36(11) . . ? C21 C20 C10 121.46(11) . . ? C22 C21 C20 120.73(12) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C23 C22 C21 121.17(12) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 117.79(12) . . ? C24 C23 C26 119.31(12) . . ? C22 C23 C26 122.77(12) . . ? C25 C24 C23 121.15(12) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C20 120.96(12) . . ? C24 C25 H25 119.5 . . ? C20 C25 H25 119.5 . . ? C23 C26 C28 113.55(12) . . ? C23 C26 C27 109.43(11) . . ? C28 C26 C27 110.41(12) . . ? C23 C26 H26 107.7 . . ? C28 C26 H26 107.7 . . ? C27 C26 H26 107.7 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O3 C29 H29A 109.5 . . ? O3 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O3 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O4 C30 H30A 109.5 . . ? O4 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O4 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C6 N1 C9 108.72(10) . . ? C4 N2 C1 110.45(10) . . ? C4 N2 H2B 124.8 . . ? C1 N2 H2B 124.8 . . ? C7 O1 H1 109.5 . . ? C8 O2 H2A 109.5 . . ? C29 O3 H3A 109.5 . . ? C30 O4 H4 109.5 . . ? 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 N2 C1 C2 C3 1.96(15) . . . . ? C10 C1 C2 C3 -175.07(13) 2_567 . . . ? C1 C2 C3 C4 -0.62(16) . . . . ? C2 C3 C4 N2 -0.97(15) . . . . ? C2 C3 C4 C5 175.94(13) . . . . ? N2 C4 C5 C6 -6.3(2) . . . . ? C3 C4 C5 C6 177.46(13) . . . . ? N2 C4 C5 C11 169.04(12) . . . . ? C3 C4 C5 C11 -7.20(19) . . . . ? C4 C5 C6 N1 3.4(2) . . . . ? C11 C5 C6 N1 -171.72(11) . . . . ? C4 C5 C6 C7 -179.05(12) . . . . ? C11 C5 C6 C7 5.86(19) . . . . ? N1 C6 C7 O1 -142.98(11) . . . . ? C5 C6 C7 O1 39.15(17) . . . . ? N1 C6 C7 C8 -20.31(13) . . . . ? C5 C6 C7 C8 161.82(12) . . . . ? O1 C7 C8 O2 28.69(15) . . . . ? C6 C7 C8 O2 -94.43(12) . . . . ? O1 C7 C8 C9 146.07(10) . . . . ? C6 C7 C8 C9 22.95(12) . . . . ? O2 C8 C9 N1 98.26(12) . . . . ? C7 C8 C9 N1 -21.31(13) . . . . ? O2 C8 C9 C10 -76.79(15) . . . . ? C7 C8 C9 C10 163.64(12) . . . . ? N1 C9 C10 C1 -0.9(2) . . . 2_567 ? C8 C9 C10 C1 173.38(12) . . . 2_567 ? N1 C9 C10 C20 -179.15(11) . . . . ? C8 C9 C10 C20 -4.85(18) . . . . ? C6 C5 C11 C12 -108.73(15) . . . . ? C4 C5 C11 C12 75.62(15) . . . . ? C6 C5 C11 C16 76.70(15) . . . . ? C4 C5 C11 C16 -98.95(14) . . . . ? C16 C11 C12 C13 0.55(19) . . . . ? C5 C11 C12 C13 -174.04(12) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C12 C13 C14 C15 -0.77(19) . . . . ? C12 C13 C14 C17 177.82(12) . . . . ? C13 C14 C15 C16 0.8(2) . . . . ? C17 C14 C15 C16 -177.83(12) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C12 C11 C16 C15 -0.56(19) . . . . ? C5 C11 C16 C15 174.20(12) . . . . ? C15 C14 C17 C18 64.07(17) . . . . ? C13 C14 C17 C18 -114.48(15) . . . . ? C15 C14 C17 C19 -60.22(17) . . . . ? C13 C14 C17 C19 121.24(14) . . . . ? C9 C10 C20 C25 110.38(15) . . . . ? C1 C10 C20 C25 -68.05(16) 2_567 . . . ? C9 C10 C20 C21 -74.10(16) . . . . ? C1 C10 C20 C21 107.47(14) 2_567 . . . ? C25 C20 C21 C22 3.19(19) . . . . ? C10 C20 C21 C22 -172.43(12) . . . . ? C20 C21 C22 C23 0.3(2) . . . . ? C21 C22 C23 C24 -3.36(19) . . . . ? C21 C22 C23 C26 172.51(12) . . . . ? C22 C23 C24 C25 3.0(2) . . . . ? C26 C23 C24 C25 -173.02(13) . . . . ? C23 C24 C25 C20 0.5(2) . . . . ? C21 C20 C25 C24 -3.6(2) . . . . ? C10 C20 C25 C24 172.11(12) . . . . ? C24 C23 C26 C28 -155.29(13) . . . . ? C22 C23 C26 C28 28.91(18) . . . . ? C24 C23 C26 C27 80.85(16) . . . . ? C22 C23 C26 C27 -94.96(16) . . . . ? C5 C6 N1 C9 -174.63(12) . . . . ? C7 C6 N1 C9 7.53(14) . . . . ? C10 C9 N1 C6 -175.94(12) . . . . ? C8 C9 N1 C6 9.26(14) . . . . ? C5 C4 N2 C1 -174.56(12) . . . . ? C3 C4 N2 C1 2.26(14) . . . . ? C10 C1 N2 C4 174.37(12) 2_567 . . . ? C2 C1 N2 C4 -2.62(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2B N1 0.88 2.42 2.9469(15) 118.6 . N2 H2B N1 0.88 2.44 2.9678(15) 119.0 2_567 O1 H1 O3 0.84 1.83 2.6664(14) 173.5 2_676 O2 H2A O4 0.84 1.85 2.6922(15) 179.5 1_456 O3 H3A O2 0.84 1.89 2.7026(13) 162.8 1_554 O4 H4 O1 0.84 1.94 2.7356(15) 157.8 2_676 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.367 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.046 data_4d _database_code_depnum_ccdc_archive 'CCDC 756649' #TrackingRef 'X-ray_Structures_Chlorins.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H58 N4 O16, 4.62(C H Cl3)' _chemical_formula_sum 'C60.62 H62.62 Cl13.86 N4 O16' _chemical_formula_weight 1594.67 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6873(9) _cell_length_b 15.6713(12) _cell_length_c 22.2525(17) _cell_angle_alpha 69.9290(10) _cell_angle_beta 82.0790(10) _cell_angle_gamma 72.1360(10) _cell_volume 3641.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6936 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 30.45 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1635.3 _exptl_absorpt_coefficient_mu 0.590 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.915 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; One chloroform molecule is inversion disordered over two sites with an occupancy ratio of 0.59(1) to 0.41(1). The carbon atoms in both moieties were constrained to have identical ADPs. Two other chloroform molecules refined to be only partially occupied with occupancy rates of 0.820(6) and 0.801(6), respectively. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 29211 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 0.97 _diffrn_reflns_theta_max 25.03 _reflns_number_total 12829 _reflns_number_gt 9870 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4' _computing_data_reduction 'Apex2 v2008.2-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.1067P)^2^+17.9934P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12829 _refine_ls_number_parameters 896 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1140 _refine_ls_R_factor_gt 0.0920 _refine_ls_wR_factor_ref 0.2518 _refine_ls_wR_factor_gt 0.2370 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.004 _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 C1 C 0.7356(4) 0.2073(3) 0.3308(2) 0.0142(10) Uani 1 1 d . . . C2 C 0.7492(5) 0.2028(4) 0.3990(2) 0.0173(11) Uani 1 1 d . . . H2 H 0.8326 0.2007 0.4064 0.021 Uiso 1 1 calc R . . C3 C 0.6571(5) 0.2948(4) 0.4025(2) 0.0169(11) Uani 1 1 d . . . H3 H 0.6986 0.3453 0.3937 0.020 Uiso 1 1 calc R . . C4 C 0.5768(5) 0.3180(4) 0.3471(2) 0.0152(10) Uani 1 1 d . . . C5 C 0.4636(5) 0.3847(3) 0.3395(2) 0.0149(10) Uani 1 1 d . . . C6 C 0.3836(4) 0.4060(3) 0.2920(2) 0.0145(10) Uani 1 1 d . . . C7 C 0.2711(5) 0.4789(4) 0.2809(2) 0.0178(11) Uani 1 1 d . . . H7 H 0.2385 0.5217 0.3046 0.021 Uiso 1 1 calc R . . C8 C 0.2193(5) 0.4761(4) 0.2307(2) 0.0175(11) Uani 1 1 d . . . H8 H 0.1443 0.5164 0.2135 0.021 Uiso 1 1 calc R . . C9 C 0.2968(4) 0.4024(3) 0.2084(2) 0.0149(10) Uani 1 1 d . . . C10 C 0.2752(4) 0.3771(3) 0.1575(2) 0.0152(10) Uani 1 1 d . . . C11 C 0.3541(4) 0.3073(3) 0.1333(2) 0.0144(10) Uani 1 1 d . . . C12 C 0.3206(4) 0.2837(4) 0.0783(2) 0.0173(11) Uani 1 1 d . . . H12 H 0.3264 0.3349 0.0371 0.021 Uiso 1 1 calc R . . C13 C 0.4217(5) 0.1929(4) 0.0795(2) 0.0188(11) Uani 1 1 d . . . H13 H 0.4507 0.1905 0.0355 0.023 Uiso 1 1 calc R . . C14 C 0.5168(4) 0.2011(3) 0.1155(2) 0.0140(10) Uani 1 1 d . . . C15 C 0.6366(4) 0.1514(3) 0.1141(2) 0.0138(10) Uani 1 1 d . . . C16 C 0.7261(4) 0.1407(3) 0.1550(2) 0.0133(10) Uani 1 1 d . . . C17 C 0.8444(5) 0.0808(4) 0.1584(2) 0.0173(11) Uani 1 1 d . . . H17 H 0.8823 0.0467 0.1297 0.021 Uiso 1 1 calc R . . C18 C 0.8954(5) 0.0802(4) 0.2108(2) 0.0167(10) Uani 1 1 d . . . H18 H 0.9745 0.0449 0.2247 0.020 Uiso 1 1 calc R . . C19 C 0.8112(4) 0.1402(3) 0.2405(2) 0.0148(10) Uani 1 1 d . . . C20 C 0.8219(4) 0.1510(3) 0.3001(2) 0.0145(10) Uani 1 1 d . . . C21 C 0.4180(4) 0.4389(4) 0.3867(2) 0.0159(10) Uani 1 1 d . . . C22 C 0.4672(4) 0.5093(3) 0.3872(2) 0.0149(10) Uani 1 1 d . . . H22 H 0.5328 0.5226 0.3589 0.018 Uiso 1 1 calc R . . C23 C 0.4183(4) 0.5597(3) 0.4299(2) 0.0160(10) Uani 1 1 d . . . C24 C 0.3234(4) 0.5405(4) 0.4713(2) 0.0170(11) Uani 1 1 d . . . C25 C 0.2749(5) 0.4693(4) 0.4708(2) 0.0181(11) Uani 1 1 d . . . C26 C 0.3239(5) 0.4184(4) 0.4284(3) 0.0206(11) Uani 1 1 d . . . H26 H 0.2924 0.3693 0.4282 0.025 Uiso 1 1 calc R . . C27 C 0.5544(5) 0.6561(4) 0.3927(3) 0.0256(12) Uani 1 1 d . . . H27A H 0.6239 0.6001 0.3987 0.038 Uiso 1 1 calc R . . H27B H 0.5760 0.7054 0.4026 0.038 Uiso 1 1 calc R . . H27C H 0.5301 0.6797 0.3482 0.038 Uiso 1 1 calc R . . C28 C 0.1825(5) 0.6751(4) 0.4863(3) 0.0259(12) Uani 1 1 d . . . H28A H 0.2127 0.7126 0.4458 0.039 Uiso 1 1 calc R . . H28B H 0.1579 0.7122 0.5158 0.039 Uiso 1 1 calc R . . H28C H 0.1133 0.6580 0.4785 0.039 Uiso 1 1 calc R . . C29 C 0.1272(6) 0.3855(5) 0.5120(3) 0.0363(15) Uani 1 1 d . . . H29A H 0.1002 0.4013 0.4687 0.054 Uiso 1 1 calc R . . H29B H 0.0582 0.3844 0.5424 0.054 Uiso 1 1 calc R . . H29C H 0.1864 0.3232 0.5237 0.054 Uiso 1 1 calc R . . C30 C 0.1579(4) 0.4321(3) 0.1268(2) 0.0141(10) Uani 1 1 d . . . C31 C 0.0520(5) 0.4122(3) 0.1551(2) 0.0161(10) Uani 1 1 d . . . H31 H 0.0545 0.3596 0.1928 0.019 Uiso 1 1 calc R . . C32 C -0.0587(4) 0.4690(3) 0.1286(2) 0.0154(10) Uani 1 1 d . . . C33 C -0.0613(4) 0.5472(3) 0.0737(2) 0.0150(10) Uani 1 1 d . . . C34 C 0.0446(5) 0.5665(4) 0.0447(2) 0.0160(10) Uani 1 1 d . . . C35 C 0.1550(5) 0.5093(3) 0.0706(2) 0.0155(10) Uani 1 1 d . . . H35 H 0.2276 0.5224 0.0504 0.019 Uiso 1 1 calc R . . C36 C -0.1682(5) 0.3682(4) 0.2017(3) 0.0239(12) Uani 1 1 d . . . H36A H -0.1178 0.3150 0.1880 0.036 Uiso 1 1 calc R . . H36B H -0.2507 0.3631 0.2106 0.036 Uiso 1 1 calc R . . H36C H -0.1364 0.3670 0.2406 0.036 Uiso 1 1 calc R . . C37 C -0.2220(5) 0.6788(4) 0.0771(3) 0.0250(12) Uani 1 1 d . . . H37A H -0.2433 0.6505 0.1223 0.038 Uiso 1 1 calc R . . H37B H -0.2943 0.7226 0.0547 0.038 Uiso 1 1 calc R . . H37C H -0.1631 0.7132 0.0741 0.038 Uiso 1 1 calc R . . C38 C 0.1369(5) 0.6639(4) -0.0430(3) 0.0265(13) Uani 1 1 d . . . H38A H 0.1880 0.6708 -0.0145 0.040 Uiso 1 1 calc R . . H38B H 0.1155 0.7224 -0.0792 0.040 Uiso 1 1 calc R . . H38C H 0.1806 0.6112 -0.0588 0.040 Uiso 1 1 calc R . . C39 C 0.6786(4) 0.0979(4) 0.0661(2) 0.0154(10) Uani 1 1 d . . . C40 C 0.6368(5) 0.0211(4) 0.0736(2) 0.0161(10) Uani 1 1 d . . . H40 H 0.5855 0.0007 0.1093 0.019 Uiso 1 1 calc R . . C41 C 0.6709(5) -0.0261(4) 0.0282(3) 0.0196(11) Uani 1 1 d . . . C42 C 0.7490(5) 0.0010(4) -0.0223(2) 0.0219(12) Uani 1 1 d . . . C43 C 0.7923(5) 0.0774(4) -0.0290(2) 0.0242(12) Uani 1 1 d . . . C44 C 0.7567(5) 0.1265(4) 0.0156(2) 0.0195(11) Uani 1 1 d . . . H44 H 0.7857 0.1787 0.0112 0.023 Uiso 1 1 calc R . . C45 C 0.5438(5) -0.1255(4) 0.0811(3) 0.0275(13) Uani 1 1 d . . . H45A H 0.5832 -0.1489 0.1220 0.041 Uiso 1 1 calc R . . H45B H 0.5153 -0.1752 0.0760 0.041 Uiso 1 1 calc R . . H45C H 0.4754 -0.0701 0.0802 0.041 Uiso 1 1 calc R . . C46 C 0.8931(5) -0.1117(5) -0.0626(3) 0.0356(15) Uani 1 1 d . . . H46A H 0.9552 -0.0821 -0.0616 0.053 Uiso 1 1 calc R . . H46B H 0.9101 -0.1363 -0.0989 0.053 Uiso 1 1 calc R . . H46C H 0.8926 -0.1638 -0.0226 0.053 Uiso 1 1 calc R . . C47 C 0.9079(8) 0.1820(7) -0.0924(3) 0.058(2) Uani 1 1 d . . . H47A H 0.8377 0.2359 -0.0926 0.087 Uiso 1 1 calc R . . H47B H 0.9512 0.1954 -0.1340 0.087 Uiso 1 1 calc R . . H47C H 0.9613 0.1712 -0.0587 0.087 Uiso 1 1 calc R . . C48 C 0.9394(4) 0.0938(3) 0.3316(2) 0.0145(10) Uani 1 1 d . . . C49 C 1.0457(5) 0.1164(4) 0.3064(2) 0.0182(11) Uani 1 1 d . . . H49 H 1.0449 0.1687 0.2686 0.022 Uiso 1 1 calc R . . C50 C 1.1535(5) 0.0627(4) 0.3363(2) 0.0177(11) Uani 1 1 d . . . C51 C 1.1547(5) -0.0129(4) 0.3925(2) 0.0179(11) Uani 1 1 d . . . C52 C 1.0483(5) -0.0346(3) 0.4179(2) 0.0180(11) Uani 1 1 d . . . C53 C 0.9406(5) 0.0171(3) 0.3868(2) 0.0174(11) Uani 1 1 d . . . H53 H 0.8685 -0.0001 0.4033 0.021 Uiso 1 1 calc R . . C54 C 1.2660(6) 0.1567(5) 0.2589(3) 0.0368(16) Uani 1 1 d . . . H54A H 1.2344 0.1486 0.2232 0.055 Uiso 1 1 calc R . . H54B H 1.3493 0.1596 0.2484 0.055 Uiso 1 1 calc R . . H54C H 1.2168 0.2155 0.2663 0.055 Uiso 1 1 calc R . . C55 C 1.3527(5) -0.1197(4) 0.3965(3) 0.0280(13) Uani 1 1 d . . . H55A H 1.3207 -0.1646 0.3872 0.042 Uiso 1 1 calc R . . H55B H 1.4198 -0.1546 0.4253 0.042 Uiso 1 1 calc R . . H55C H 1.3811 -0.0796 0.3565 0.042 Uiso 1 1 calc R . . C56 C 0.9481(5) -0.1286(4) 0.5027(3) 0.0267(13) Uani 1 1 d . . . H56A H 0.8903 -0.0711 0.5081 0.040 Uiso 1 1 calc R . . H56B H 0.9641 -0.1774 0.5447 0.040 Uiso 1 1 calc R . . H56C H 0.9149 -0.1515 0.4751 0.040 Uiso 1 1 calc R . . C57 C 0.5610(5) 0.5521(4) 0.1033(3) 0.0295(13) Uani 1 1 d . . . H57 H 0.6443 0.5571 0.0891 0.035 Uiso 1 1 calc R . . C58 C 0.8789(6) 0.4936(5) 0.3486(3) 0.0392(16) Uani 1 1 d . . . H58 H 0.8342 0.4903 0.3906 0.047 Uiso 1 1 calc R . . C60 C 0.7123(12) 0.9100(8) 0.2724(6) 0.078(4) Uani 0.820(6) 1 d P . . H60 H 0.7631 0.9543 0.2524 0.094 Uiso 0.820(6) 1 calc PR . . C61 C 0.2302(10) 0.8578(7) 0.2174(5) 0.058(3) Uani 0.801(6) 1 d P . . H61 H 0.1876 0.8928 0.1762 0.070 Uiso 0.801(6) 1 calc PR . . Cl1 Cl 0.54955(14) 0.44675(11) 0.09799(9) 0.0390(4) Uani 1 1 d . . . Cl2 Cl 0.53465(15) 0.55291(13) 0.18332(8) 0.0415(4) Uani 1 1 d . . . Cl3 Cl 0.45773(15) 0.65103(12) 0.05345(9) 0.0426(4) Uani 1 1 d . . . Cl4 Cl 0.97396(16) 0.38033(13) 0.35300(8) 0.0469(5) Uani 1 1 d . . . Cl5 Cl 0.77346(15) 0.53133(14) 0.28812(8) 0.0457(5) Uani 1 1 d . . . Cl6 Cl 0.96280(17) 0.57491(15) 0.33271(10) 0.0531(5) Uani 1 1 d . . . Cl7 Cl 0.2515(3) 0.22899(18) 0.38966(14) 0.0849(8) Uani 1 1 d . . . C59 C 0.3497(14) 0.1298(11) 0.4239(6) 0.055(3) Uani 0.591(13) 1 d P A 1 H59 H 0.3109 0.0787 0.4294 0.066 Uiso 0.591(13) 1 calc PR A 1 Cl8 Cl 0.3740(12) 0.1243(9) 0.5012(6) 0.154(5) Uani 0.591(13) 1 d P A 1 C59B C 0.423(2) 0.1452(15) 0.4276(9) 0.055(3) Uani 0.409(13) 1 d P A 2 H59B H 0.4665 0.1905 0.4292 0.066 Uiso 0.409(13) 1 calc PR A 2 Cl18 Cl 0.3920(10) 0.0899(15) 0.5010(4) 0.139(7) Uani 0.409(13) 1 d P A 2 Cl9 Cl 0.4866(3) 0.1046(3) 0.37462(16) 0.1133(13) Uani 1 1 d . . . Cl10 Cl 0.5685(3) 0.9712(3) 0.25220(16) 0.0881(12) Uani 0.820(6) 1 d P . . Cl11 Cl 0.7358(7) 0.8669(5) 0.3528(2) 0.181(3) Uani 0.820(6) 1 d P . . Cl12 Cl 0.7639(6) 0.8151(4) 0.2393(3) 0.178(3) Uani 0.820(6) 1 d P . . Cl13 Cl 0.3081(6) 0.9272(3) 0.22824(16) 0.129(2) Uani 0.801(6) 1 d P . . Cl14 Cl 0.3307(4) 0.7532(3) 0.2096(2) 0.0993(14) Uani 0.801(6) 1 d P . . Cl15 Cl 0.1235(4) 0.8375(3) 0.27750(19) 0.1070(16) Uani 0.801(6) 1 d P . . N1 N 0.6289(4) 0.2679(3) 0.30689(18) 0.0121(8) Uani 1 1 d . . . N2 N 0.3948(4) 0.3627(3) 0.24636(18) 0.0123(8) Uani 1 1 d . . . H2A H 0.4567 0.3159 0.2421 0.015 Uiso 1 1 calc R . . N3 N 0.4670(4) 0.2600(3) 0.15135(19) 0.0133(8) Uani 1 1 d . . . N4 N 0.7098(4) 0.1770(3) 0.20464(19) 0.0136(9) Uani 1 1 d . . . H4 H 0.6438 0.2180 0.2125 0.016 Uiso 1 1 calc R . . O1 O 0.7155(4) 0.1218(3) 0.44023(17) 0.0250(9) Uani 1 1 d . . . H1 H 0.7161 0.1195 0.4785 0.038 Uiso 1 1 calc R . . O2 O 0.5979(4) 0.2817(3) 0.46340(17) 0.0233(8) Uani 1 1 d . . . H2B H 0.5996 0.3244 0.4776 0.035 Uiso 1 1 calc R . . O3 O 0.2060(3) 0.2668(3) 0.08494(17) 0.0208(8) Uani 1 1 d . . . H3A H 0.1615 0.3088 0.0562 0.031 Uiso 1 1 calc R . . O4 O 0.3876(3) 0.1099(2) 0.11825(17) 0.0201(8) Uani 1 1 d . . . H4B H 0.3406 0.0991 0.0982 0.030 Uiso 1 1 calc R . . O5 O 0.4569(3) 0.6315(3) 0.43443(18) 0.0222(8) Uani 1 1 d . . . O6 O 0.2759(3) 0.5905(3) 0.51409(17) 0.0210(8) Uani 1 1 d . . . O7 O 0.1813(3) 0.4555(3) 0.51379(18) 0.0247(9) Uani 1 1 d . . . O8 O -0.1676(3) 0.4555(2) 0.15192(17) 0.0202(8) Uani 1 1 d . . . O9 O -0.1711(3) 0.6053(2) 0.04828(16) 0.0179(8) Uani 1 1 d . . . O10 O 0.0304(3) 0.6455(3) -0.00863(17) 0.0222(8) Uani 1 1 d . . . O11 O 0.6279(3) -0.0996(3) 0.02987(19) 0.0235(8) Uani 1 1 d . . . O12 O 0.7768(4) -0.0422(3) -0.06957(19) 0.0301(10) Uani 1 1 d . . . O13 O 0.8691(4) 0.0994(3) -0.08076(19) 0.0334(10) Uani 1 1 d . . . O14 O 1.0576(3) -0.1079(3) 0.47412(17) 0.0248(9) Uani 1 1 d . . . O15 O 1.2591(3) -0.0613(3) 0.42658(17) 0.0234(8) Uani 1 1 d . . . O16 O 1.2626(3) 0.0784(3) 0.31533(18) 0.0231(8) Uani 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 C1 0.017(3) 0.015(2) 0.012(2) -0.006(2) -0.0068(19) -0.002(2) C2 0.021(3) 0.017(3) 0.012(2) -0.005(2) -0.009(2) 0.001(2) C3 0.025(3) 0.015(2) 0.011(2) -0.006(2) -0.008(2) -0.001(2) C4 0.018(3) 0.018(3) 0.012(2) -0.008(2) -0.005(2) -0.004(2) C5 0.021(3) 0.014(2) 0.011(2) -0.006(2) -0.003(2) -0.005(2) C6 0.017(3) 0.016(2) 0.012(2) -0.007(2) -0.0046(19) -0.002(2) C7 0.019(3) 0.020(3) 0.016(3) -0.012(2) -0.002(2) 0.000(2) C8 0.014(2) 0.018(3) 0.019(3) -0.009(2) -0.004(2) 0.003(2) C9 0.014(2) 0.014(2) 0.015(2) -0.005(2) -0.0062(19) 0.001(2) C10 0.017(3) 0.016(2) 0.012(2) -0.005(2) -0.0044(19) 0.000(2) C11 0.019(3) 0.015(2) 0.008(2) -0.0026(19) -0.0051(19) -0.003(2) C12 0.016(3) 0.022(3) 0.015(3) -0.010(2) -0.010(2) 0.001(2) C13 0.018(3) 0.022(3) 0.017(3) -0.010(2) -0.010(2) 0.002(2) C14 0.019(3) 0.012(2) 0.012(2) -0.0033(19) -0.0061(19) -0.002(2) C15 0.020(3) 0.012(2) 0.011(2) -0.0066(19) -0.0044(19) -0.001(2) C16 0.017(2) 0.013(2) 0.009(2) -0.0056(19) -0.0020(19) -0.001(2) C17 0.017(3) 0.018(3) 0.017(3) -0.009(2) -0.003(2) 0.001(2) C18 0.015(2) 0.016(3) 0.017(3) -0.005(2) -0.006(2) 0.000(2) C19 0.018(3) 0.013(2) 0.013(2) -0.004(2) -0.006(2) -0.001(2) C20 0.019(3) 0.010(2) 0.012(2) -0.0027(19) -0.009(2) 0.001(2) C21 0.018(3) 0.016(2) 0.012(2) -0.007(2) -0.006(2) 0.003(2) C22 0.013(2) 0.016(2) 0.015(2) -0.006(2) -0.0041(19) -0.001(2) C23 0.016(3) 0.014(2) 0.020(3) -0.010(2) -0.007(2) 0.000(2) C24 0.017(3) 0.019(3) 0.015(2) -0.010(2) -0.008(2) 0.001(2) C25 0.017(3) 0.025(3) 0.014(2) -0.010(2) -0.002(2) -0.004(2) C26 0.024(3) 0.021(3) 0.021(3) -0.012(2) -0.006(2) -0.004(2) C27 0.029(3) 0.026(3) 0.029(3) -0.016(3) 0.003(2) -0.011(2) C28 0.025(3) 0.027(3) 0.028(3) -0.017(3) -0.004(2) 0.002(2) C29 0.040(4) 0.052(4) 0.033(3) -0.025(3) 0.013(3) -0.028(3) C30 0.016(3) 0.015(2) 0.013(2) -0.009(2) -0.0047(19) -0.001(2) C31 0.020(3) 0.010(2) 0.015(2) -0.003(2) -0.008(2) 0.003(2) C32 0.017(3) 0.016(2) 0.015(2) -0.006(2) -0.005(2) -0.002(2) C33 0.015(2) 0.014(2) 0.014(2) -0.004(2) -0.0093(19) 0.003(2) C34 0.018(3) 0.017(3) 0.010(2) -0.003(2) -0.0055(19) -0.001(2) C35 0.017(3) 0.018(3) 0.011(2) -0.007(2) -0.0052(19) 0.000(2) C36 0.018(3) 0.024(3) 0.022(3) 0.002(2) -0.005(2) -0.005(2) C37 0.024(3) 0.016(3) 0.029(3) -0.008(2) -0.007(2) 0.005(2) C38 0.026(3) 0.026(3) 0.022(3) 0.000(2) 0.001(2) -0.008(2) C39 0.013(2) 0.019(3) 0.015(2) -0.010(2) -0.0100(19) 0.004(2) C40 0.018(3) 0.018(3) 0.014(2) -0.010(2) -0.005(2) 0.000(2) C41 0.018(3) 0.018(3) 0.024(3) -0.012(2) -0.009(2) 0.003(2) C42 0.017(3) 0.031(3) 0.018(3) -0.016(2) -0.010(2) 0.005(2) C43 0.022(3) 0.036(3) 0.014(3) -0.010(2) -0.005(2) -0.003(2) C44 0.020(3) 0.027(3) 0.014(3) -0.008(2) -0.009(2) -0.003(2) C45 0.025(3) 0.023(3) 0.039(3) -0.018(3) -0.007(3) -0.002(2) C46 0.020(3) 0.047(4) 0.048(4) -0.036(3) 0.009(3) -0.002(3) C47 0.075(6) 0.098(7) 0.025(4) -0.027(4) 0.018(4) -0.057(5) C48 0.018(3) 0.014(2) 0.011(2) -0.006(2) -0.0066(19) 0.001(2) C49 0.024(3) 0.015(3) 0.014(2) -0.003(2) -0.010(2) -0.001(2) C50 0.020(3) 0.018(3) 0.016(3) -0.008(2) -0.007(2) -0.001(2) C51 0.020(3) 0.016(3) 0.017(3) -0.007(2) -0.009(2) 0.002(2) C52 0.028(3) 0.013(2) 0.010(2) -0.003(2) -0.005(2) -0.001(2) C53 0.019(3) 0.015(2) 0.018(3) -0.007(2) -0.008(2) 0.001(2) C54 0.027(3) 0.034(4) 0.034(4) 0.011(3) -0.007(3) -0.010(3) C55 0.022(3) 0.028(3) 0.023(3) -0.005(2) 0.001(2) 0.004(2) C56 0.027(3) 0.020(3) 0.022(3) 0.001(2) -0.006(2) 0.001(2) C57 0.026(3) 0.026(3) 0.033(3) -0.007(3) -0.002(3) -0.006(3) C58 0.033(4) 0.053(4) 0.025(3) -0.018(3) 0.000(3) 0.002(3) C60 0.088(9) 0.059(7) 0.070(8) 0.021(6) -0.020(7) -0.038(7) C61 0.078(7) 0.050(6) 0.044(6) -0.019(5) -0.026(5) 0.001(5) Cl1 0.0318(8) 0.0322(8) 0.0568(10) -0.0183(8) 0.0024(7) -0.0114(7) Cl2 0.0377(9) 0.0493(10) 0.0334(9) -0.0143(8) 0.0013(7) -0.0061(8) Cl3 0.0343(9) 0.0341(9) 0.0473(10) 0.0029(7) -0.0125(7) -0.0055(7) Cl4 0.0451(10) 0.0490(10) 0.0342(9) -0.0123(8) -0.0050(7) 0.0046(8) Cl5 0.0374(9) 0.0586(11) 0.0351(9) -0.0200(8) -0.0074(7) 0.0033(8) Cl6 0.0472(11) 0.0653(12) 0.0541(11) -0.0345(10) 0.0078(9) -0.0127(9) Cl7 0.119(2) 0.0624(15) 0.0908(19) -0.0397(14) 0.0272(16) -0.0455(15) C59 0.071(9) 0.059(7) 0.042(6) -0.017(5) 0.003(6) -0.031(7) Cl8 0.188(10) 0.145(7) 0.170(9) -0.094(7) -0.083(7) -0.021(6) C59B 0.071(9) 0.059(7) 0.042(6) -0.017(5) 0.003(6) -0.031(7) Cl18 0.080(6) 0.32(2) 0.025(4) -0.017(6) 0.013(3) -0.110(9) Cl9 0.0626(17) 0.183(4) 0.090(2) -0.018(2) -0.0020(15) -0.057(2) Cl10 0.078(2) 0.101(3) 0.065(2) -0.0130(17) 0.0198(16) -0.0207(18) Cl11 0.271(8) 0.228(7) 0.073(3) 0.015(3) -0.074(4) -0.153(6) Cl12 0.209(6) 0.101(3) 0.209(6) -0.084(4) -0.131(5) 0.067(4) Cl13 0.260(6) 0.123(3) 0.0469(18) -0.0150(19) -0.032(3) -0.116(4) Cl14 0.096(3) 0.073(2) 0.117(3) -0.052(2) -0.022(2) 0.0257(19) Cl15 0.102(3) 0.084(3) 0.082(2) -0.0029(19) 0.014(2) 0.014(2) N1 0.013(2) 0.013(2) 0.0100(19) -0.0046(16) -0.0032(16) -0.0014(16) N2 0.013(2) 0.014(2) 0.0097(19) -0.0083(16) -0.0048(16) 0.0026(16) N3 0.015(2) 0.011(2) 0.013(2) -0.0040(16) -0.0064(16) 0.0006(16) N4 0.012(2) 0.016(2) 0.013(2) -0.0085(17) -0.0063(16) 0.0021(16) O1 0.042(2) 0.0191(19) 0.0127(18) -0.0034(15) -0.0070(17) -0.0055(17) O2 0.035(2) 0.024(2) 0.0134(18) -0.0113(16) -0.0037(16) -0.0048(17) O3 0.0200(19) 0.024(2) 0.0186(19) -0.0085(16) -0.0094(15) -0.0013(16) O4 0.0189(19) 0.0163(18) 0.025(2) -0.0064(16) -0.0110(15) -0.0014(15) O5 0.023(2) 0.023(2) 0.029(2) -0.0196(17) 0.0004(16) -0.0044(16) O6 0.0219(19) 0.026(2) 0.0208(19) -0.0202(16) -0.0016(15) 0.0007(16) O7 0.023(2) 0.038(2) 0.025(2) -0.0226(18) 0.0088(16) -0.0163(18) O8 0.0159(18) 0.0172(18) 0.0218(19) 0.0008(15) -0.0064(15) -0.0023(15) O9 0.0154(18) 0.0146(18) 0.0190(18) -0.0063(15) -0.0096(14) 0.0072(14) O10 0.023(2) 0.0175(19) 0.0160(18) 0.0027(15) -0.0031(15) 0.0010(15) O11 0.024(2) 0.021(2) 0.031(2) -0.0197(17) -0.0044(16) -0.0005(16) O12 0.026(2) 0.040(2) 0.029(2) -0.027(2) -0.0062(17) 0.0051(18) O13 0.036(2) 0.052(3) 0.019(2) -0.019(2) 0.0076(17) -0.018(2) O14 0.025(2) 0.021(2) 0.0150(18) 0.0048(15) -0.0061(15) 0.0023(16) O15 0.0184(19) 0.027(2) 0.0170(19) -0.0056(16) -0.0112(15) 0.0075(16) O16 0.0184(19) 0.0207(19) 0.023(2) 0.0017(16) -0.0083(15) -0.0020(15) _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 C1 N1 1.359(6) . ? C1 C20 1.393(7) . ? C1 C2 1.524(6) . ? C2 O1 1.420(6) . ? C2 C3 1.532(7) . ? C2 H2 1.0000 . ? C3 O2 1.412(6) . ? C3 C4 1.529(6) . ? C3 H3 1.0000 . ? C4 N1 1.352(6) . ? C4 C5 1.401(7) . ? C5 C6 1.395(7) . ? C5 C21 1.511(7) . ? C6 N2 1.374(6) . ? C6 C7 1.438(7) . ? C7 C8 1.360(7) . ? C7 H7 0.9500 . ? C8 C9 1.424(7) . ? C8 H8 0.9500 . ? C9 N2 1.372(6) . ? C9 C10 1.397(7) . ? C10 C11 1.409(7) . ? C10 C30 1.489(7) . ? C11 N3 1.339(6) . ? C11 C12 1.524(6) . ? C12 O3 1.422(6) . ? C12 C13 1.540(7) . ? C12 H12 1.0000 . ? C13 O4 1.431(7) . ? C13 C14 1.516(7) . ? C13 H13 1.0000 . ? C14 N3 1.369(6) . ? C14 C15 1.379(7) . ? C15 C16 1.414(7) . ? C15 C39 1.518(6) . ? C16 N4 1.374(6) . ? C16 C17 1.408(7) . ? C17 C18 1.377(7) . ? C17 H17 0.9500 . ? C18 C19 1.402(7) . ? C18 H18 0.9500 . ? C19 N4 1.378(6) . ? C19 C20 1.421(7) . ? C20 C48 1.503(6) . ? C21 C26 1.380(8) . ? C21 C22 1.396(7) . ? C22 C23 1.395(7) . ? C22 H22 0.9500 . ? C23 O5 1.371(6) . ? C23 C24 1.379(7) . ? C24 O6 1.390(6) . ? C24 C25 1.401(7) . ? C25 O7 1.368(6) . ? C25 C26 1.394(7) . ? C26 H26 0.9500 . ? C27 O5 1.429(7) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 O6 1.437(6) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 O7 1.437(7) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.383(7) . ? C30 C35 1.407(7) . ? C31 C32 1.399(7) . ? C31 H31 0.9500 . ? C32 O8 1.357(6) . ? C32 C33 1.399(7) . ? C33 C34 1.383(7) . ? C33 O9 1.388(6) . ? C34 O10 1.375(6) . ? C34 C35 1.392(7) . ? C35 H35 0.9500 . ? C36 O8 1.436(6) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 O9 1.440(6) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 O10 1.422(7) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.383(7) . ? C39 C44 1.386(8) . ? C40 C41 1.397(7) . ? C40 H40 0.9500 . ? C41 O11 1.378(6) . ? C41 C42 1.380(8) . ? C42 O12 1.389(6) . ? C42 C43 1.393(8) . ? C43 O13 1.373(7) . ? C43 C44 1.400(7) . ? C44 H44 0.9500 . ? C45 O11 1.431(7) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 O12 1.446(7) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 O13 1.430(9) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 C49 1.388(7) . ? C48 C53 1.392(7) . ? C49 C50 1.390(7) . ? C49 H49 0.9500 . ? C50 O16 1.363(6) . ? C50 C51 1.395(7) . ? C51 C52 1.383(8) . ? C51 O15 1.390(6) . ? C52 O14 1.369(6) . ? C52 C53 1.396(7) . ? C53 H53 0.9500 . ? C54 O16 1.429(7) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 O15 1.445(7) . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 O14 1.426(7) . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 Cl1 1.740(6) . ? C57 Cl3 1.769(6) . ? C57 Cl2 1.770(6) . ? C57 H57 1.0000 . ? C58 Cl6 1.753(8) . ? C58 Cl4 1.759(7) . ? C58 Cl5 1.773(7) . ? C58 H58 1.0000 . ? C60 Cl10 1.694(13) . ? C60 Cl11 1.711(12) . ? C60 Cl12 1.789(15) . ? C60 H60 1.0000 . ? C61 Cl13 1.709(12) . ? C61 Cl15 1.715(12) . ? C61 Cl14 1.748(10) . ? C61 H61 1.0000 . ? Cl7 C59 1.627(15) . ? Cl7 C59B 2.13(2) . ? C59 Cl8 1.752(17) . ? C59 Cl9 1.828(15) . ? C59 H59 1.0000 . ? C59B Cl9 1.53(2) . ? C59B Cl18 1.62(2) . ? C59B H59B 1.0000 . ? N2 H2A 0.8800 . ? N4 H4 0.8800 . ? O1 H1 0.8400 . ? O2 H2B 0.8400 . ? O3 H3A 0.8400 . ? O4 H4B 0.8400 . ? 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 C1 C20 126.3(4) . . ? N1 C1 C2 111.6(4) . . ? C20 C1 C2 122.0(4) . . ? O1 C2 C1 106.6(4) . . ? O1 C2 C3 111.9(4) . . ? C1 C2 C3 101.6(4) . . ? O1 C2 H2 112.1 . . ? C1 C2 H2 112.1 . . ? C3 C2 H2 112.1 . . ? O2 C3 C4 115.0(4) . . ? O2 C3 C2 110.9(4) . . ? C4 C3 C2 101.7(4) . . ? O2 C3 H3 109.6 . . ? C4 C3 H3 109.6 . . ? C2 C3 H3 109.6 . . ? N1 C4 C5 125.1(4) . . ? N1 C4 C3 112.0(4) . . ? C5 C4 C3 122.9(4) . . ? C6 C5 C4 125.9(4) . . ? C6 C5 C21 114.4(4) . . ? C4 C5 C21 119.7(4) . . ? N2 C6 C5 127.8(4) . . ? N2 C6 C7 105.8(4) . . ? C5 C6 C7 126.4(4) . . ? C8 C7 C6 108.3(4) . . ? C8 C7 H7 125.8 . . ? C6 C7 H7 125.8 . . ? C7 C8 C9 108.4(4) . . ? C7 C8 H8 125.8 . . ? C9 C8 H8 125.8 . . ? N2 C9 C10 127.7(4) . . ? N2 C9 C8 106.5(4) . . ? C10 C9 C8 125.8(4) . . ? C9 C10 C11 125.9(4) . . ? C9 C10 C30 114.9(4) . . ? C11 C10 C30 119.2(4) . . ? N3 C11 C10 125.7(4) . . ? N3 C11 C12 112.4(4) . . ? C10 C11 C12 121.8(4) . . ? O3 C12 C11 115.5(4) . . ? O3 C12 C13 110.5(4) . . ? C11 C12 C13 101.4(4) . . ? O3 C12 H12 109.7 . . ? C11 C12 H12 109.7 . . ? C13 C12 H12 109.7 . . ? O4 C13 C14 106.3(4) . . ? O4 C13 C12 111.6(4) . . ? C14 C13 C12 101.3(4) . . ? O4 C13 H13 112.3 . . ? C14 C13 H13 112.3 . . ? C12 C13 H13 112.3 . . ? N3 C14 C15 125.2(4) . . ? N3 C14 C13 111.2(4) . . ? C15 C14 C13 123.5(4) . . ? C14 C15 C16 127.1(4) . . ? C14 C15 C39 117.9(4) . . ? C16 C15 C39 114.9(4) . . ? N4 C16 C17 106.5(4) . . ? N4 C16 C15 126.4(4) . . ? C17 C16 C15 126.6(4) . . ? C18 C17 C16 108.0(4) . . ? C18 C17 H17 126.0 . . ? C16 C17 H17 126.0 . . ? C17 C18 C19 108.7(4) . . ? C17 C18 H18 125.6 . . ? C19 C18 H18 125.6 . . ? N4 C19 C18 106.2(4) . . ? N4 C19 C20 126.5(4) . . ? C18 C19 C20 126.8(4) . . ? C1 C20 C19 126.5(4) . . ? C1 C20 C48 119.0(4) . . ? C19 C20 C48 114.5(4) . . ? C26 C21 C22 120.7(5) . . ? C26 C21 C5 118.1(5) . . ? C22 C21 C5 121.2(5) . . ? C23 C22 C21 118.8(5) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? O5 C23 C24 114.6(4) . . ? O5 C23 C22 124.6(5) . . ? C24 C23 C22 120.9(5) . . ? C23 C24 O6 120.5(4) . . ? C23 C24 C25 120.0(4) . . ? O6 C24 C25 119.4(5) . . ? O7 C25 C26 125.2(5) . . ? O7 C25 C24 115.5(4) . . ? C26 C25 C24 119.2(5) . . ? C21 C26 C25 120.3(5) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? O5 C27 H27A 109.5 . . ? O5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 H28A 109.5 . . ? O6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O7 C29 H29A 109.5 . . ? O7 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O7 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 C35 120.0(4) . . ? C31 C30 C10 120.9(4) . . ? C35 C30 C10 118.9(4) . . ? C30 C31 C32 120.5(5) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? O8 C32 C33 115.4(4) . . ? O8 C32 C31 125.5(5) . . ? C33 C32 C31 119.2(5) . . ? C34 C33 O9 120.1(4) . . ? C34 C33 C32 120.4(4) . . ? O9 C33 C32 119.4(4) . . ? O10 C34 C33 115.0(4) . . ? O10 C34 C35 124.5(5) . . ? C33 C34 C35 120.4(5) . . ? C34 C35 C30 119.4(5) . . ? C34 C35 H35 120.3 . . ? C30 C35 H35 120.3 . . ? O8 C36 H36A 109.5 . . ? O8 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O8 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O9 C37 H37A 109.5 . . ? O9 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O9 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O10 C38 H38A 109.5 . . ? O10 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O10 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 C44 121.1(5) . . ? C40 C39 C15 118.7(5) . . ? C44 C39 C15 120.1(5) . . ? C39 C40 C41 119.2(5) . . ? C39 C40 H40 120.4 . . ? C41 C40 H40 120.4 . . ? O11 C41 C42 116.4(4) . . ? O11 C41 C40 123.0(5) . . ? C42 C41 C40 120.6(5) . . ? C41 C42 O12 120.4(5) . . ? C41 C42 C43 119.9(5) . . ? O12 C42 C43 119.6(5) . . ? O13 C43 C42 115.7(5) . . ? O13 C43 C44 124.2(5) . . ? C42 C43 C44 120.0(5) . . ? C39 C44 C43 119.2(5) . . ? C39 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? O11 C45 H45A 109.5 . . ? O11 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? O11 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O12 C46 H46A 109.5 . . ? O12 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O12 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O13 C47 H47A 109.5 . . ? O13 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? O13 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C49 C48 C53 120.0(4) . . ? C49 C48 C20 121.0(4) . . ? C53 C48 C20 119.0(5) . . ? C48 C49 C50 120.1(5) . . ? C48 C49 H49 119.9 . . ? C50 C49 H49 119.9 . . ? O16 C50 C49 124.8(5) . . ? O16 C50 C51 115.1(4) . . ? C49 C50 C51 120.1(5) . . ? C52 C51 O15 119.3(5) . . ? C52 C51 C50 119.6(5) . . ? O15 C51 C50 120.9(5) . . ? O14 C52 C51 115.5(4) . . ? O14 C52 C53 124.0(5) . . ? C51 C52 C53 120.6(5) . . ? C48 C53 C52 119.6(5) . . ? C48 C53 H53 120.2 . . ? C52 C53 H53 120.2 . . ? O16 C54 H54A 109.5 . . ? O16 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? O16 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? O15 C55 H55A 109.5 . . ? O15 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? O15 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? O14 C56 H56A 109.5 . . ? O14 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? O14 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? Cl1 C57 Cl3 111.2(3) . . ? Cl1 C57 Cl2 110.4(3) . . ? Cl3 C57 Cl2 109.4(3) . . ? Cl1 C57 H57 108.6 . . ? Cl3 C57 H57 108.6 . . ? Cl2 C57 H57 108.6 . . ? Cl6 C58 Cl4 110.7(4) . . ? Cl6 C58 Cl5 110.0(4) . . ? Cl4 C58 Cl5 109.9(4) . . ? Cl6 C58 H58 108.7 . . ? Cl4 C58 H58 108.7 . . ? Cl5 C58 H58 108.7 . . ? Cl10 C60 Cl11 115.0(9) . . ? Cl10 C60 Cl12 110.1(7) . . ? Cl11 C60 Cl12 109.5(7) . . ? Cl10 C60 H60 107.3 . . ? Cl11 C60 H60 107.3 . . ? Cl12 C60 H60 107.3 . . ? Cl13 C61 Cl15 111.3(6) . . ? Cl13 C61 Cl14 109.7(7) . . ? Cl15 C61 Cl14 112.6(6) . . ? Cl13 C61 H61 107.7 . . ? Cl15 C61 H61 107.7 . . ? Cl14 C61 H61 107.7 . . ? Cl7 C59 Cl8 109.8(9) . . ? Cl7 C59 Cl9 113.6(8) . . ? Cl8 C59 Cl9 114.7(10) . . ? Cl7 C59 H59 106.0 . . ? Cl8 C59 H59 106.0 . . ? Cl9 C59 H59 106.0 . . ? Cl9 C59B Cl18 129.0(17) . . ? Cl9 C59B Cl7 103.1(11) . . ? Cl18 C59B Cl7 103.7(12) . . ? Cl9 C59B H59B 106.4 . . ? Cl18 C59B H59B 106.4 . . ? Cl7 C59B H59B 106.4 . . ? C4 N1 C1 108.8(4) . . ? C9 N2 C6 111.0(4) . . ? C9 N2 H2A 124.5 . . ? C6 N2 H2A 124.5 . . ? C11 N3 C14 108.8(4) . . ? C16 N4 C19 110.5(4) . . ? C16 N4 H4 124.7 . . ? C19 N4 H4 124.7 . . ? C2 O1 H1 109.5 . . ? C3 O2 H2B 109.5 . . ? C12 O3 H3A 109.5 . . ? C13 O4 H4B 109.5 . . ? C23 O5 C27 117.8(4) . . ? C24 O6 C28 111.7(4) . . ? C25 O7 C29 116.1(4) . . ? C32 O8 C36 117.1(4) . . ? C33 O9 C37 111.7(4) . . ? C34 O10 C38 117.0(4) . . ? C41 O11 C45 116.3(4) . . ? C42 O12 C46 113.2(4) . . ? C43 O13 C47 117.6(5) . . ? C52 O14 C56 116.5(4) . . ? C51 O15 C55 115.5(4) . . ? C50 O16 C54 117.4(4) . . ? 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 O1 97.6(5) . . . . ? C20 C1 C2 O1 -79.4(6) . . . . ? N1 C1 C2 C3 -19.7(5) . . . . ? C20 C1 C2 C3 163.3(5) . . . . ? O1 C2 C3 O2 28.8(6) . . . . ? C1 C2 C3 O2 142.2(4) . . . . ? O1 C2 C3 C4 -94.0(5) . . . . ? C1 C2 C3 C4 19.4(5) . . . . ? O2 C3 C4 N1 -135.5(4) . . . . ? C2 C3 C4 N1 -15.6(6) . . . . ? O2 C3 C4 C5 45.4(7) . . . . ? C2 C3 C4 C5 165.3(5) . . . . ? N1 C4 C5 C6 4.3(8) . . . . ? C3 C4 C5 C6 -176.8(5) . . . . ? N1 C4 C5 C21 -177.5(5) . . . . ? C3 C4 C5 C21 1.5(7) . . . . ? C4 C5 C6 N2 4.7(9) . . . . ? C21 C5 C6 N2 -173.7(5) . . . . ? C4 C5 C6 C7 -175.2(5) . . . . ? C21 C5 C6 C7 6.4(8) . . . . ? N2 C6 C7 C8 0.7(6) . . . . ? C5 C6 C7 C8 -179.3(5) . . . . ? C6 C7 C8 C9 -0.3(6) . . . . ? C7 C8 C9 N2 -0.3(6) . . . . ? C7 C8 C9 C10 179.9(5) . . . . ? N2 C9 C10 C11 -2.9(9) . . . . ? C8 C9 C10 C11 176.8(5) . . . . ? N2 C9 C10 C30 178.2(5) . . . . ? C8 C9 C10 C30 -2.1(8) . . . . ? C9 C10 C11 N3 -6.6(9) . . . . ? C30 C10 C11 N3 172.2(5) . . . . ? C9 C10 C11 C12 178.7(5) . . . . ? C30 C10 C11 C12 -2.5(7) . . . . ? N3 C11 C12 O3 135.0(4) . . . . ? C10 C11 C12 O3 -49.7(7) . . . . ? N3 C11 C12 C13 15.5(6) . . . . ? C10 C11 C12 C13 -169.2(5) . . . . ? O3 C12 C13 O4 -30.7(5) . . . . ? C11 C12 C13 O4 92.3(5) . . . . ? O3 C12 C13 C14 -143.5(4) . . . . ? C11 C12 C13 C14 -20.5(5) . . . . ? O4 C13 C14 N3 -95.1(5) . . . . ? C12 C13 C14 N3 21.6(5) . . . . ? O4 C13 C14 C15 81.9(6) . . . . ? C12 C13 C14 C15 -161.5(5) . . . . ? N3 C14 C15 C16 9.5(8) . . . . ? C13 C14 C15 C16 -167.0(5) . . . . ? N3 C14 C15 C39 -173.4(5) . . . . ? C13 C14 C15 C39 10.1(7) . . . . ? C14 C15 C16 N4 1.2(9) . . . . ? C39 C15 C16 N4 -176.0(5) . . . . ? C14 C15 C16 C17 171.7(5) . . . . ? C39 C15 C16 C17 -5.4(7) . . . . ? N4 C16 C17 C18 1.6(6) . . . . ? C15 C16 C17 C18 -170.5(5) . . . . ? C16 C17 C18 C19 -0.7(6) . . . . ? C17 C18 C19 N4 -0.4(6) . . . . ? C17 C18 C19 C20 171.8(5) . . . . ? N1 C1 C20 C19 -5.5(8) . . . . ? C2 C1 C20 C19 171.0(5) . . . . ? N1 C1 C20 C48 175.1(5) . . . . ? C2 C1 C20 C48 -8.4(7) . . . . ? N4 C19 C20 C1 -6.0(9) . . . . ? C18 C19 C20 C1 -176.6(5) . . . . ? N4 C19 C20 C48 173.5(5) . . . . ? C18 C19 C20 C48 2.8(8) . . . . ? C6 C5 C21 C26 68.9(6) . . . . ? C4 C5 C21 C26 -109.6(6) . . . . ? C6 C5 C21 C22 -109.6(5) . . . . ? C4 C5 C21 C22 72.0(6) . . . . ? C26 C21 C22 C23 -1.0(7) . . . . ? C5 C21 C22 C23 177.4(4) . . . . ? C21 C22 C23 O5 -178.8(4) . . . . ? C21 C22 C23 C24 0.3(7) . . . . ? O5 C23 C24 O6 -1.4(7) . . . . ? C22 C23 C24 O6 179.4(4) . . . . ? O5 C23 C24 C25 179.3(4) . . . . ? C22 C23 C24 C25 0.1(7) . . . . ? C23 C24 C25 O7 179.8(4) . . . . ? O6 C24 C25 O7 0.5(7) . . . . ? C23 C24 C25 C26 0.2(7) . . . . ? O6 C24 C25 C26 -179.1(4) . . . . ? C22 C21 C26 C25 1.4(8) . . . . ? C5 C21 C26 C25 -177.1(5) . . . . ? O7 C25 C26 C21 179.5(5) . . . . ? C24 C25 C26 C21 -1.0(8) . . . . ? C9 C10 C30 C31 -77.9(6) . . . . ? C11 C10 C30 C31 103.1(6) . . . . ? C9 C10 C30 C35 97.6(6) . . . . ? C11 C10 C30 C35 -81.3(6) . . . . ? C35 C30 C31 C32 -0.7(7) . . . . ? C10 C30 C31 C32 174.8(4) . . . . ? C30 C31 C32 O8 179.2(5) . . . . ? C30 C31 C32 C33 -1.0(7) . . . . ? O8 C32 C33 C34 -178.2(4) . . . . ? C31 C32 C33 C34 2.0(7) . . . . ? O8 C32 C33 O9 1.6(7) . . . . ? C31 C32 C33 O9 -178.2(4) . . . . ? O9 C33 C34 O10 0.7(7) . . . . ? C32 C33 C34 O10 -179.6(4) . . . . ? O9 C33 C34 C35 179.0(4) . . . . ? C32 C33 C34 C35 -1.2(7) . . . . ? O10 C34 C35 C30 177.7(4) . . . . ? C33 C34 C35 C30 -0.5(7) . . . . ? C31 C30 C35 C34 1.4(7) . . . . ? C10 C30 C35 C34 -174.1(4) . . . . ? C14 C15 C39 C40 -66.9(6) . . . . ? C16 C15 C39 C40 110.5(5) . . . . ? C14 C15 C39 C44 112.6(5) . . . . ? C16 C15 C39 C44 -69.9(6) . . . . ? C44 C39 C40 C41 -2.3(7) . . . . ? C15 C39 C40 C41 177.3(4) . . . . ? C39 C40 C41 O11 -176.1(4) . . . . ? C39 C40 C41 C42 2.5(7) . . . . ? O11 C41 C42 O12 2.7(7) . . . . ? C40 C41 C42 O12 -176.0(4) . . . . ? O11 C41 C42 C43 177.2(4) . . . . ? C40 C41 C42 C43 -1.5(7) . . . . ? C41 C42 C43 O13 -179.8(5) . . . . ? O12 C42 C43 O13 -5.2(7) . . . . ? C41 C42 C43 C44 0.1(8) . . . . ? O12 C42 C43 C44 174.7(5) . . . . ? C40 C39 C44 C43 0.9(7) . . . . ? C15 C39 C44 C43 -178.6(4) . . . . ? O13 C43 C44 C39 -180.0(5) . . . . ? C42 C43 C44 C39 0.2(7) . . . . ? C1 C20 C48 C49 -110.5(6) . . . . ? C19 C20 C48 C49 70.0(6) . . . . ? C1 C20 C48 C53 69.6(6) . . . . ? C19 C20 C48 C53 -109.8(5) . . . . ? C53 C48 C49 C50 -0.2(7) . . . . ? C20 C48 C49 C50 180.0(4) . . . . ? C48 C49 C50 O16 179.6(5) . . . . ? C48 C49 C50 C51 -1.4(7) . . . . ? O16 C50 C51 C52 179.9(4) . . . . ? C49 C50 C51 C52 0.8(7) . . . . ? O16 C50 C51 O15 5.6(7) . . . . ? C49 C50 C51 O15 -173.4(5) . . . . ? O15 C51 C52 O14 -3.8(7) . . . . ? C50 C51 C52 O14 -178.1(4) . . . . ? O15 C51 C52 C53 175.8(4) . . . . ? C50 C51 C52 C53 1.5(7) . . . . ? C49 C48 C53 C52 2.4(7) . . . . ? C20 C48 C53 C52 -177.7(4) . . . . ? O14 C52 C53 C48 176.4(4) . . . . ? C51 C52 C53 C48 -3.1(7) . . . . ? C59B Cl7 C59 Cl8 69.5(17) . . . . ? C59B Cl7 C59 Cl9 -60.4(16) . . . . ? C59 Cl7 C59B Cl9 78.6(18) . . . . ? C59 Cl7 C59B Cl18 -57.6(17) . . . . ? Cl18 C59B Cl9 C59 75(2) . . . . ? Cl7 C59B Cl9 C59 -45.6(13) . . . . ? Cl7 C59 Cl9 C59B 95.6(19) . . . . ? Cl8 C59 Cl9 C59B -31.8(16) . . . . ? C5 C4 N1 C1 -177.3(5) . . . . ? C3 C4 N1 C1 3.6(6) . . . . ? C20 C1 N1 C4 -172.6(5) . . . . ? C2 C1 N1 C4 10.5(6) . . . . ? C10 C9 N2 C6 -179.4(5) . . . . ? C8 C9 N2 C6 0.8(6) . . . . ? C5 C6 N2 C9 179.1(5) . . . . ? C7 C6 N2 C9 -1.0(6) . . . . ? C10 C11 N3 C14 -177.4(5) . . . . ? C12 C11 N3 C14 -2.3(6) . . . . ? C15 C14 N3 C11 170.4(5) . . . . ? C13 C14 N3 C11 -12.8(6) . . . . ? C17 C16 N4 C19 -1.9(6) . . . . ? C15 C16 N4 C19 170.2(5) . . . . ? C18 C19 N4 C16 1.5(6) . . . . ? C20 C19 N4 C16 -170.7(5) . . . . ? C24 C23 O5 C27 -179.5(4) . . . . ? C22 C23 O5 C27 -0.4(7) . . . . ? C23 C24 O6 C28 88.5(6) . . . . ? C25 C24 O6 C28 -92.2(6) . . . . ? C26 C25 O7 C29 -3.1(8) . . . . ? C24 C25 O7 C29 177.4(5) . . . . ? C33 C32 O8 C36 170.2(4) . . . . ? C31 C32 O8 C36 -10.0(7) . . . . ? C34 C33 O9 C37 -92.8(6) . . . . ? C32 C33 O9 C37 87.5(5) . . . . ? C33 C34 O10 C38 -175.1(5) . . . . ? C35 C34 O10 C38 6.6(7) . . . . ? C42 C41 O11 C45 -178.0(4) . . . . ? C40 C41 O11 C45 0.6(7) . . . . ? C41 C42 O12 C46 -102.0(6) . . . . ? C43 C42 O12 C46 83.4(6) . . . . ? C42 C43 O13 C47 175.0(6) . . . . ? C44 C43 O13 C47 -4.9(8) . . . . ? C51 C52 O14 C56 177.1(5) . . . . ? C53 C52 O14 C56 -2.5(7) . . . . ? C52 C51 O15 C55 115.2(5) . . . . ? C50 C51 O15 C55 -70.6(6) . . . . ? C49 C50 O16 C54 0.8(8) . . . . ? C51 C50 O16 C54 -178.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.208 _refine_diff_density_min -1.393 _refine_diff_density_rms 0.116 # start Validation Reply Form _vrf_PLAT222_4d ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.80 Ratio RESPONSE: The H atom in question is part of a methoxy group that is more flexible than the majority of the stiff porphyrine backbone. ; _vrf_PLAT220_4d ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.46 Ratio RESPONSE: The C atom in question is part of a methoxy group that is more flexible than the majority of the stiff porphyrine backbone. ; # end Validation Reply Form data_5a _database_code_depnum_ccdc_archive 'CCDC 756650' #TrackingRef 'X-ray_Structures_Chlorins.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H36 N4 O2' _chemical_formula_sum 'C46 H36 N4 O2' _chemical_formula_weight 676.79 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.3828(4) _cell_length_b 10.2429(3) _cell_length_c 24.0675(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.0890(10) _cell_angle_gamma 90.00 _cell_volume 3510.38(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8753 _cell_measurement_theta_min 1.71 _cell_measurement_theta_max 28.29 _exptl_crystal_description 'triangular plate' _exptl_crystal_colour 'dark purple' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9843 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details 'SADABS v2.03, Sheldrick' _exptl_special_details ; The first 50 frames of data were recollected for a decay correction. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 \s(I). Note that the absorption correction parameters Tmin and Tmax also reflect beam corrections, etc. As a result, the numberical values for Tmin and Tmax may differ from expected values based solely on absorption effects and crystal size. ; _publ_section_acknowledgements ; Funding for the SMART6000 diffractometer through NSF-MRI grant CHE-0215950 is gratefully acknowledged. ; _diffrn_ambient_temperature 150(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 SMART6000 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 47955 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.29 _reflns_number_total 8719 _reflns_number_gt 5928 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART v5.628' _computing_cell_refinement 'Bruker SAINT v6.28A' _computing_data_reduction 'Bruker SAINT v6.28A' _computing_structure_solution 'Bruker SHELXTL v6.12' _computing_structure_refinement 'Bruker SHELXTL v6.14' _computing_molecular_graphics 'Bruker SHELXTL v6.12' _computing_publication_material 'Bruker SHELXTL v6.14' _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 nitrogen H-atoms were located from the difference map and held fixed at that location. The remaining H-atoms were either calculated or located directly and treated with a riding model. ; _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^)+(0.0468P)^2^+1.4071P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8719 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1177 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 N1 N 0.00420(8) 0.59254(12) 0.10175(5) 0.0254(3) Uani 1 1 d . . . O1 O -0.20575(7) 0.72623(11) 0.07228(5) 0.0321(3) Uani 1 1 d . . . C1 C -0.05710(10) 0.63811(14) 0.05780(6) 0.0248(3) Uani 1 1 d . . . O2 O -0.20808(7) 0.54587(11) 0.15440(5) 0.0310(2) Uani 1 1 d . . . C2 C -0.15893(10) 0.60805(15) 0.06342(6) 0.0263(3) Uani 1 1 d . . . H2A H -0.1906 0.5622 0.0292 0.032 Uiso 1 1 calc R . . N2 N 0.16368(8) 0.52695(13) 0.19082(5) 0.0266(3) Uani 1 1 d . . . H2 H 0.1616 0.5726 0.1615 0.032 Uiso 1 1 d . . . C3 C -0.14818(10) 0.51602(15) 0.11477(6) 0.0259(3) Uani 1 1 d . . . H3A H -0.1608 0.4244 0.1014 0.031 Uiso 1 1 calc R . . N3 N 0.29362(8) 0.62674(12) 0.11806(5) 0.0262(3) Uani 1 1 d . . . C4 C -0.04433(10) 0.52884(14) 0.13772(6) 0.0244(3) Uani 1 1 d . . . N4 N 0.14112(8) 0.70573(12) 0.03275(5) 0.0258(3) Uani 1 1 d . . . H4 H 0.1516 0.6753 0.0665 0.031 Uiso 1 1 d . . . C5 C -0.00609(10) 0.47242(15) 0.18878(6) 0.0266(3) Uani 1 1 d . . . C6 C 0.08978(10) 0.46999(15) 0.21157(6) 0.0269(3) Uani 1 1 d . . . C7 C 0.12840(11) 0.39812(16) 0.26025(7) 0.0320(3) Uani 1 1 d . . . H7 H 0.0937 0.3500 0.2841 0.038 Uiso 1 1 calc R . . C8 C 0.22371(11) 0.41062(16) 0.26652(7) 0.0315(3) Uani 1 1 d . . . H8 H 0.2669 0.3715 0.2952 0.038 Uiso 1 1 calc R . . C9 C 0.24757(10) 0.49221(15) 0.22271(6) 0.0265(3) Uani 1 1 d . . . C10 C 0.33730(10) 0.52426(15) 0.21129(6) 0.0263(3) Uani 1 1 d . . . C11 C 0.35751(10) 0.59191(15) 0.16324(6) 0.0262(3) Uani 1 1 d . . . C12 C 0.45160(10) 0.63091(16) 0.15498(6) 0.0289(3) Uani 1 1 d . . . H12 H 0.5074 0.6199 0.1808 0.035 Uiso 1 1 calc R . . C13 C 0.44465(10) 0.68568(16) 0.10375(6) 0.0292(3) Uani 1 1 d . . . H13 H 0.4945 0.7201 0.0862 0.035 Uiso 1 1 calc R . . C14 C 0.34588(10) 0.68168(15) 0.08068(6) 0.0266(3) Uani 1 1 d . . . C15 C 0.31067(10) 0.72906(15) 0.02683(6) 0.0268(3) Uani 1 1 d . . . C16 C 0.21556(10) 0.74119(14) 0.00542(6) 0.0257(3) Uani 1 1 d . . . C17 C 0.17560(11) 0.79388(15) -0.04721(6) 0.0287(3) Uani 1 1 d . . . H17 H 0.2094 0.8261 -0.0755 0.034 Uiso 1 1 calc R . . C18 C 0.08009(11) 0.79007(15) -0.04999(6) 0.0287(3) Uani 1 1 d . . . H18 H 0.0362 0.8202 -0.0805 0.034 Uiso 1 1 calc R . . C19 C 0.05726(10) 0.73366(14) 0.00027(6) 0.0254(3) Uani 1 1 d . . . C20 C -0.03382(10) 0.70720(14) 0.01205(6) 0.0256(3) Uani 1 1 d . . . C21 C -0.30126(12) 0.7292(2) 0.04740(9) 0.0480(5) Uani 1 1 d . . . H21A H -0.3049 0.7214 0.0066 0.072 Uiso 1 1 calc R . . H21B H -0.3297 0.8119 0.0567 0.072 Uiso 1 1 calc R . . H21C H -0.3351 0.6564 0.0618 0.072 Uiso 1 1 calc R . . C22 C -0.29025(11) 0.46595(19) 0.15005(8) 0.0423(4) Uani 1 1 d . . . H22A H -0.2725 0.3741 0.1471 0.063 Uiso 1 1 calc R . . H22B H -0.3335 0.4909 0.1166 0.063 Uiso 1 1 calc R . . H22C H -0.3211 0.4780 0.1835 0.063 Uiso 1 1 calc R . . C23 C -0.06992(10) 0.40100(16) 0.22260(6) 0.0286(3) Uani 1 1 d . . . C24 C -0.09869(12) 0.45936(18) 0.26967(7) 0.0382(4) Uani 1 1 d . . . H24 H -0.0766 0.5441 0.2808 0.046 Uiso 1 1 calc R . . C25 C -0.15895(13) 0.3951(2) 0.30028(8) 0.0465(5) Uani 1 1 d . . . H25 H -0.1788 0.4363 0.3320 0.056 Uiso 1 1 calc R . . C26 C -0.19055(12) 0.2708(2) 0.28500(8) 0.0469(5) Uani 1 1 d . . . H26 H -0.2326 0.2270 0.3058 0.056 Uiso 1 1 calc R . . C27 C -0.16073(12) 0.21075(19) 0.23938(8) 0.0444(5) Uani 1 1 d . . . H27 H -0.1813 0.1248 0.2292 0.053 Uiso 1 1 calc R . . C28 C -0.10058(11) 0.27568(17) 0.20807(7) 0.0353(4) Uani 1 1 d . . . H28 H -0.0805 0.2338 0.1766 0.042 Uiso 1 1 calc R . . C29 C 0.41832(10) 0.47218(15) 0.25089(6) 0.0273(3) Uani 1 1 d . . . C30 C 0.43043(11) 0.50239(17) 0.30786(7) 0.0331(4) Uani 1 1 d . . . H30 H 0.3882 0.5607 0.3222 0.040 Uiso 1 1 calc R . . C31 C 0.50420(12) 0.44743(18) 0.34393(7) 0.0399(4) Uani 1 1 d . . . H31 H 0.5109 0.4665 0.3829 0.048 Uiso 1 1 calc R . . C32 C 0.56766(12) 0.36549(18) 0.32352(8) 0.0416(4) Uani 1 1 d . . . H32 H 0.6185 0.3296 0.3482 0.050 Uiso 1 1 calc R . . C33 C 0.55685(12) 0.33599(18) 0.26697(8) 0.0411(4) Uani 1 1 d . . . H33 H 0.6006 0.2800 0.2527 0.049 Uiso 1 1 calc R . . C34 C 0.48245(11) 0.38778(17) 0.23108(7) 0.0341(4) Uani 1 1 d . . . H34 H 0.4749 0.3656 0.1924 0.041 Uiso 1 1 calc R . . C35 C 0.37978(10) 0.76772(16) -0.01122(6) 0.0301(3) Uani 1 1 d . . . C36 C 0.43858(11) 0.67325(19) -0.02955(7) 0.0369(4) Uani 1 1 d . . . H36 H 0.4356 0.5859 -0.0167 0.044 Uiso 1 1 calc R . . C37 C 0.50112(12) 0.7053(2) -0.06620(7) 0.0474(5) Uani 1 1 d . . . H37 H 0.5407 0.6401 -0.0784 0.057 Uiso 1 1 calc R . . C38 C 0.50580(13) 0.8319(2) -0.08491(8) 0.0547(6) Uani 1 1 d . . . H38 H 0.5480 0.8538 -0.1105 0.066 Uiso 1 1 calc R . . C39 C 0.44926(14) 0.9270(2) -0.06647(9) 0.0544(5) Uani 1 1 d . . . H39 H 0.4534 1.0145 -0.0790 0.065 Uiso 1 1 calc R . . C40 C 0.38658(12) 0.89527(19) -0.02981(8) 0.0411(4) Uani 1 1 d . . . H40 H 0.3480 0.9612 -0.0173 0.049 Uiso 1 1 calc R . . C41 C -0.11146(10) 0.76002(15) -0.03063(6) 0.0256(3) Uani 1 1 d . . . C42 C -0.13303(11) 0.89233(16) -0.03120(7) 0.0319(3) Uani 1 1 d . . . H42 H -0.1001 0.9484 -0.0037 0.038 Uiso 1 1 calc R . . C43 C -0.20206(11) 0.94350(17) -0.07137(7) 0.0354(4) Uani 1 1 d . . . H43 H -0.2159 1.0342 -0.0714 0.042 Uiso 1 1 calc R . . C44 C -0.25051(11) 0.86288(17) -0.11121(7) 0.0338(4) Uani 1 1 d . . . H44 H -0.2975 0.8979 -0.1389 0.041 Uiso 1 1 calc R . . C45 C -0.23057(12) 0.73080(18) -0.11077(7) 0.0395(4) Uani 1 1 d . . . H45 H -0.2645 0.6748 -0.1379 0.047 Uiso 1 1 calc R . . C46 C -0.16102(12) 0.67973(17) -0.07073(7) 0.0351(4) Uani 1 1 d . . . H46 H -0.1473 0.5890 -0.0708 0.042 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 0.0218(6) 0.0279(6) 0.0263(6) -0.0013(5) 0.0027(5) 0.0017(5) O1 0.0248(5) 0.0334(6) 0.0373(6) 0.0001(5) 0.0019(5) 0.0072(4) C1 0.0214(7) 0.0252(7) 0.0275(7) -0.0047(6) 0.0019(6) 0.0014(5) O2 0.0221(5) 0.0364(6) 0.0356(6) -0.0022(5) 0.0081(4) 0.0000(4) C2 0.0210(7) 0.0295(8) 0.0278(7) -0.0047(6) 0.0013(6) 0.0008(6) N2 0.0212(6) 0.0326(7) 0.0256(6) 0.0035(5) 0.0021(5) -0.0008(5) C3 0.0213(7) 0.0266(7) 0.0297(7) -0.0043(6) 0.0037(6) -0.0006(6) N3 0.0218(6) 0.0302(7) 0.0264(6) 0.0009(5) 0.0023(5) -0.0005(5) C4 0.0200(7) 0.0255(7) 0.0279(7) -0.0034(6) 0.0040(6) 0.0006(5) N4 0.0224(6) 0.0293(7) 0.0253(6) 0.0013(5) 0.0024(5) 0.0007(5) C5 0.0218(7) 0.0289(8) 0.0293(8) -0.0011(6) 0.0040(6) -0.0005(6) C6 0.0238(7) 0.0300(8) 0.0272(7) 0.0007(6) 0.0050(6) -0.0017(6) C7 0.0277(8) 0.0371(9) 0.0313(8) 0.0054(7) 0.0042(6) -0.0038(7) C8 0.0262(8) 0.0385(9) 0.0289(8) 0.0048(7) 0.0005(6) -0.0012(6) C9 0.0225(7) 0.0306(8) 0.0259(7) -0.0001(6) 0.0013(6) -0.0001(6) C10 0.0226(7) 0.0295(8) 0.0259(7) -0.0027(6) 0.0005(6) -0.0005(6) C11 0.0202(7) 0.0297(8) 0.0283(7) -0.0031(6) 0.0018(6) -0.0003(6) C12 0.0199(7) 0.0364(9) 0.0299(8) -0.0029(7) 0.0017(6) -0.0012(6) C13 0.0215(7) 0.0348(8) 0.0317(8) -0.0017(7) 0.0048(6) -0.0033(6) C14 0.0224(7) 0.0281(8) 0.0292(7) -0.0014(6) 0.0036(6) -0.0001(6) C15 0.0238(7) 0.0264(8) 0.0305(8) -0.0018(6) 0.0051(6) -0.0005(6) C16 0.0249(7) 0.0256(8) 0.0272(7) -0.0016(6) 0.0059(6) -0.0002(6) C17 0.0293(8) 0.0316(8) 0.0261(7) 0.0006(6) 0.0062(6) 0.0016(6) C18 0.0280(8) 0.0319(8) 0.0260(7) 0.0001(6) 0.0028(6) 0.0043(6) C19 0.0240(7) 0.0253(7) 0.0260(7) -0.0018(6) 0.0013(6) 0.0017(6) C20 0.0236(7) 0.0254(7) 0.0272(7) -0.0043(6) 0.0020(6) 0.0019(6) C21 0.0253(8) 0.0572(12) 0.0605(12) 0.0105(10) 0.0027(8) 0.0105(8) C22 0.0241(8) 0.0460(11) 0.0577(11) 0.0045(9) 0.0089(8) -0.0035(7) C23 0.0196(7) 0.0350(8) 0.0309(8) 0.0051(7) 0.0024(6) 0.0011(6) C24 0.0371(9) 0.0405(10) 0.0386(9) 0.0051(8) 0.0111(7) 0.0021(7) C25 0.0417(10) 0.0576(13) 0.0441(10) 0.0156(9) 0.0192(8) 0.0131(9) C26 0.0237(8) 0.0623(13) 0.0557(12) 0.0289(10) 0.0093(8) 0.0017(8) C27 0.0341(9) 0.0419(10) 0.0538(11) 0.0162(9) -0.0051(8) -0.0101(8) C28 0.0308(8) 0.0369(9) 0.0366(9) 0.0047(7) -0.0003(7) -0.0028(7) C29 0.0214(7) 0.0314(8) 0.0281(7) 0.0008(6) 0.0001(6) -0.0032(6) C30 0.0296(8) 0.0398(9) 0.0294(8) -0.0013(7) 0.0027(7) -0.0021(7) C31 0.0398(9) 0.0476(11) 0.0294(8) 0.0041(8) -0.0057(7) -0.0096(8) C32 0.0300(8) 0.0429(10) 0.0479(10) 0.0151(8) -0.0082(8) -0.0033(7) C33 0.0301(9) 0.0388(10) 0.0531(11) 0.0046(8) 0.0014(8) 0.0066(7) C34 0.0301(8) 0.0378(9) 0.0335(8) -0.0014(7) 0.0014(7) 0.0032(7) C35 0.0232(7) 0.0398(9) 0.0270(8) 0.0009(7) 0.0026(6) -0.0024(6) C36 0.0288(8) 0.0495(11) 0.0320(8) -0.0011(8) 0.0029(7) 0.0030(7) C37 0.0298(9) 0.0785(15) 0.0351(9) -0.0040(10) 0.0086(7) 0.0075(9) C38 0.0324(10) 0.0928(17) 0.0409(10) 0.0078(11) 0.0122(8) -0.0105(10) C39 0.0457(11) 0.0630(14) 0.0568(12) 0.0158(10) 0.0145(10) -0.0139(10) C40 0.0352(9) 0.0438(10) 0.0456(10) 0.0045(8) 0.0103(8) -0.0050(8) C41 0.0216(7) 0.0314(8) 0.0242(7) -0.0009(6) 0.0040(6) 0.0025(6) C42 0.0309(8) 0.0302(8) 0.0337(8) -0.0050(7) 0.0012(7) 0.0005(6) C43 0.0343(9) 0.0306(8) 0.0419(9) 0.0040(7) 0.0072(7) 0.0076(7) C44 0.0253(8) 0.0464(10) 0.0295(8) 0.0067(7) 0.0033(6) 0.0070(7) C45 0.0392(9) 0.0419(10) 0.0340(9) -0.0061(7) -0.0070(7) 0.0003(8) C46 0.0379(9) 0.0300(8) 0.0351(8) -0.0061(7) -0.0026(7) 0.0043(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.3537(19) . ? N1 C1 1.3607(18) . ? O1 C2 1.4159(18) . ? O1 C21 1.4196(19) . ? C1 C20 1.389(2) . ? C1 C2 1.521(2) . ? O2 C3 1.4061(18) . ? O2 C22 1.4293(19) . ? C2 C3 1.545(2) . ? C2 H2A 1.0000 . ? N2 C6 1.3672(19) . ? N2 C9 1.3824(18) . ? N2 H2 0.8433 . ? C3 C4 1.5235(19) . ? C3 H3A 1.0000 . ? N3 C11 1.3684(18) . ? N3 C14 1.3715(19) . ? C4 C5 1.399(2) . ? N4 C19 1.3720(18) . ? N4 C16 1.3818(19) . ? N4 H4 0.8632 . ? C5 C6 1.411(2) . ? C5 C23 1.500(2) . ? C6 C7 1.428(2) . ? C7 C8 1.364(2) . ? C7 H7 0.9500 . ? C8 C9 1.425(2) . ? C8 H8 0.9500 . ? C9 C10 1.396(2) . ? C10 C11 1.413(2) . ? C10 C29 1.496(2) . ? C11 C12 1.451(2) . ? C12 C13 1.346(2) . ? C12 H12 0.9500 . ? C13 C14 1.451(2) . ? C13 H13 0.9500 . ? C14 C15 1.410(2) . ? C15 C16 1.398(2) . ? C15 C35 1.496(2) . ? C16 C17 1.422(2) . ? C17 C18 1.366(2) . ? C17 H17 0.9500 . ? C18 C19 1.420(2) . ? C18 H18 0.9500 . ? C19 C20 1.405(2) . ? C20 C41 1.507(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C28 1.386(2) . ? C23 C24 1.394(2) . ? C24 C25 1.381(2) . ? C24 H24 0.9500 . ? C25 C26 1.384(3) . ? C25 H25 0.9500 . ? C26 C27 1.378(3) . ? C26 H26 0.9500 . ? C27 C28 1.394(2) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.393(2) . ? C29 C34 1.396(2) . ? C30 C31 1.392(2) . ? C30 H30 0.9500 . ? C31 C32 1.380(3) . ? C31 H31 0.9500 . ? C32 C33 1.381(3) . ? C32 H32 0.9500 . ? C33 C34 1.383(2) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C40 1.389(2) . ? C35 C36 1.397(2) . ? C36 C37 1.385(2) . ? C36 H36 0.9500 . ? C37 C38 1.378(3) . ? C37 H37 0.9500 . ? C38 C39 1.382(3) . ? C38 H38 0.9500 . ? C39 C40 1.386(3) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C46 1.387(2) . ? C41 C42 1.390(2) . ? C42 C43 1.387(2) . ? C42 H42 0.9500 . ? C43 C44 1.378(2) . ? C43 H43 0.9500 . ? C44 C45 1.383(2) . ? C44 H44 0.9500 . ? C45 C46 1.390(2) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? 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 C4 N1 C1 109.05(12) . . ? C2 O1 C21 114.05(13) . . ? N1 C1 C20 126.08(13) . . ? N1 C1 C2 112.84(13) . . ? C20 C1 C2 121.08(13) . . ? C3 O2 C22 113.90(12) . . ? O1 C2 C1 108.95(12) . . ? O1 C2 C3 113.42(12) . . ? C1 C2 C3 101.85(11) . . ? O1 C2 H2A 110.8 . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? C6 N2 C9 110.49(12) . . ? C6 N2 H2 127.2 . . ? C9 N2 H2 122.2 . . ? O2 C3 C4 113.48(12) . . ? O2 C3 C2 114.09(12) . . ? C4 C3 C2 102.72(12) . . ? O2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? C11 N3 C14 105.04(12) . . ? N1 C4 C5 125.92(13) . . ? N1 C4 C3 112.16(12) . . ? C5 C4 C3 121.82(13) . . ? C19 N4 C16 110.60(12) . . ? C19 N4 H4 129.4 . . ? C16 N4 H4 119.9 . . ? C4 C5 C6 126.23(14) . . ? C4 C5 C23 118.89(12) . . ? C6 C5 C23 114.81(13) . . ? N2 C6 C5 128.17(14) . . ? N2 C6 C7 106.68(12) . . ? C5 C6 C7 125.04(14) . . ? C8 C7 C6 108.14(14) . . ? C8 C7 H7 125.9 . . ? C6 C7 H7 125.9 . . ? C7 C8 C9 108.43(14) . . ? C7 C8 H8 125.8 . . ? C9 C8 H8 125.8 . . ? N2 C9 C10 126.08(14) . . ? N2 C9 C8 106.24(13) . . ? C10 C9 C8 127.54(14) . . ? C9 C10 C11 125.37(13) . . ? C9 C10 C29 116.71(13) . . ? C11 C10 C29 117.70(13) . . ? N3 C11 C10 125.85(13) . . ? N3 C11 C12 110.75(13) . . ? C10 C11 C12 123.38(13) . . ? C13 C12 C11 106.84(13) . . ? C13 C12 H12 126.6 . . ? C11 C12 H12 126.6 . . ? C12 C13 C14 106.34(13) . . ? C12 C13 H13 126.8 . . ? C14 C13 H13 126.8 . . ? N3 C14 C15 125.81(13) . . ? N3 C14 C13 110.98(13) . . ? C15 C14 C13 123.21(14) . . ? C16 C15 C14 125.16(14) . . ? C16 C15 C35 116.80(13) . . ? C14 C15 C35 118.04(13) . . ? N4 C16 C15 125.79(13) . . ? N4 C16 C17 106.31(12) . . ? C15 C16 C17 127.89(14) . . ? C18 C17 C16 108.08(13) . . ? C18 C17 H17 126.0 . . ? C16 C17 H17 126.0 . . ? C17 C18 C19 108.75(13) . . ? C17 C18 H18 125.6 . . ? C19 C18 H18 125.6 . . ? N4 C19 C20 127.93(14) . . ? N4 C19 C18 106.26(13) . . ? C20 C19 C18 125.75(13) . . ? C1 C20 C19 126.43(13) . . ? C1 C20 C41 119.01(13) . . ? C19 C20 C41 114.56(13) . . ? O1 C21 H21A 109.5 . . ? O1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 118.81(15) . . ? C28 C23 C5 120.78(14) . . ? C24 C23 C5 120.40(14) . . ? C25 C24 C23 120.61(17) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 120.27(18) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C27 C26 C25 119.64(16) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C28 120.29(18) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C23 C28 C27 120.34(17) . . ? C23 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C30 C29 C34 118.47(14) . . ? C30 C29 C10 121.76(14) . . ? C34 C29 C10 119.74(13) . . ? C31 C30 C29 120.20(16) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C32 C31 C30 120.54(16) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C33 119.69(15) . . ? C31 C32 H32 120.2 . . ? C33 C32 H32 120.2 . . ? C32 C33 C34 120.09(17) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C33 C34 C29 120.97(16) . . ? C33 C34 H34 119.5 . . ? C29 C34 H34 119.5 . . ? C40 C35 C36 118.47(15) . . ? C40 C35 C15 121.94(15) . . ? C36 C35 C15 119.59(15) . . ? C37 C36 C35 120.90(18) . . ? C37 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? C38 C37 C36 119.80(19) . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C37 C38 C39 120.07(18) . . ? C37 C38 H38 120.0 . . ? C39 C38 H38 120.0 . . ? C38 C39 C40 120.2(2) . . ? C38 C39 H39 119.9 . . ? C40 C39 H39 119.9 . . ? C39 C40 C35 120.50(19) . . ? C39 C40 H40 119.8 . . ? C35 C40 H40 119.8 . . ? C46 C41 C42 118.64(14) . . ? C46 C41 C20 121.37(14) . . ? C42 C41 C20 119.97(13) . . ? C43 C42 C41 120.80(15) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C44 C43 C42 120.05(15) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C43 C44 C45 119.80(15) . . ? C43 C44 H44 120.1 . . ? C45 C44 H44 120.1 . . ? C44 C45 C46 120.12(15) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C41 C46 C45 120.58(15) . . ? C41 C46 H46 119.7 . . ? C45 C46 H46 119.7 . . ? 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 C4 N1 C1 C20 -179.27(14) . . . . ? C4 N1 C1 C2 1.83(17) . . . . ? C21 O1 C2 C1 145.57(14) . . . . ? C21 O1 C2 C3 -101.76(15) . . . . ? N1 C1 C2 O1 111.54(13) . . . . ? C20 C1 C2 O1 -67.43(17) . . . . ? N1 C1 C2 C3 -8.55(16) . . . . ? C20 C1 C2 C3 172.48(13) . . . . ? C22 O2 C3 C4 -143.36(13) . . . . ? C22 O2 C3 C2 99.44(15) . . . . ? O1 C2 C3 O2 17.23(17) . . . . ? C1 C2 C3 O2 134.13(12) . . . . ? O1 C2 C3 C4 -106.02(13) . . . . ? C1 C2 C3 C4 10.88(14) . . . . ? C1 N1 C4 C5 -177.63(14) . . . . ? C1 N1 C4 C3 6.19(16) . . . . ? O2 C3 C4 N1 -134.86(13) . . . . ? C2 C3 C4 N1 -11.20(16) . . . . ? O2 C3 C4 C5 48.79(19) . . . . ? C2 C3 C4 C5 172.44(13) . . . . ? N1 C4 C5 C6 -1.0(3) . . . . ? C3 C4 C5 C6 174.83(14) . . . . ? N1 C4 C5 C23 -177.79(14) . . . . ? C3 C4 C5 C23 -2.0(2) . . . . ? C9 N2 C6 C5 -174.62(15) . . . . ? C9 N2 C6 C7 1.72(17) . . . . ? C4 C5 C6 N2 3.9(3) . . . . ? C23 C5 C6 N2 -179.22(15) . . . . ? C4 C5 C6 C7 -171.84(15) . . . . ? C23 C5 C6 C7 5.1(2) . . . . ? N2 C6 C7 C8 -1.66(18) . . . . ? C5 C6 C7 C8 174.83(15) . . . . ? C6 C7 C8 C9 0.99(19) . . . . ? C6 N2 C9 C10 174.87(15) . . . . ? C6 N2 C9 C8 -1.13(17) . . . . ? C7 C8 C9 N2 0.05(18) . . . . ? C7 C8 C9 C10 -175.87(16) . . . . ? N2 C9 C10 C11 -3.7(3) . . . . ? C8 C9 C10 C11 171.44(16) . . . . ? N2 C9 C10 C29 -178.10(14) . . . . ? C8 C9 C10 C29 -2.9(2) . . . . ? C14 N3 C11 C10 -176.00(15) . . . . ? C14 N3 C11 C12 2.47(16) . . . . ? C9 C10 C11 N3 -6.1(3) . . . . ? C29 C10 C11 N3 168.25(14) . . . . ? C9 C10 C11 C12 175.64(15) . . . . ? C29 C10 C11 C12 -10.0(2) . . . . ? N3 C11 C12 C13 -1.99(18) . . . . ? C10 C11 C12 C13 176.52(15) . . . . ? C11 C12 C13 C14 0.63(17) . . . . ? C11 N3 C14 C15 178.01(15) . . . . ? C11 N3 C14 C13 -2.08(17) . . . . ? C12 C13 C14 N3 0.90(18) . . . . ? C12 C13 C14 C15 -179.18(15) . . . . ? N3 C14 C15 C16 7.7(2) . . . . ? C13 C14 C15 C16 -172.17(15) . . . . ? N3 C14 C15 C35 -171.20(14) . . . . ? C13 C14 C15 C35 8.9(2) . . . . ? C19 N4 C16 C15 178.59(14) . . . . ? C19 N4 C16 C17 -0.19(16) . . . . ? C14 C15 C16 N4 -1.8(2) . . . . ? C35 C15 C16 N4 177.10(14) . . . . ? C14 C15 C16 C17 176.67(15) . . . . ? C35 C15 C16 C17 -4.4(2) . . . . ? N4 C16 C17 C18 0.56(17) . . . . ? C15 C16 C17 C18 -178.19(15) . . . . ? C16 C17 C18 C19 -0.72(18) . . . . ? C16 N4 C19 C20 176.96(14) . . . . ? C16 N4 C19 C18 -0.24(16) . . . . ? C17 C18 C19 N4 0.60(17) . . . . ? C17 C18 C19 C20 -176.68(15) . . . . ? N1 C1 C20 C19 5.6(2) . . . . ? C2 C1 C20 C19 -175.60(14) . . . . ? N1 C1 C20 C41 -175.00(13) . . . . ? C2 C1 C20 C41 3.8(2) . . . . ? N4 C19 C20 C1 -5.0(3) . . . . ? C18 C19 C20 C1 171.66(15) . . . . ? N4 C19 C20 C41 175.53(14) . . . . ? C18 C19 C20 C41 -7.8(2) . . . . ? C4 C5 C23 C28 77.85(19) . . . . ? C6 C5 C23 C28 -99.29(17) . . . . ? C4 C5 C23 C24 -102.80(18) . . . . ? C6 C5 C23 C24 80.06(18) . . . . ? C28 C23 C24 C25 -1.9(2) . . . . ? C5 C23 C24 C25 178.69(15) . . . . ? C23 C24 C25 C26 0.9(3) . . . . ? C24 C25 C26 C27 0.7(3) . . . . ? C25 C26 C27 C28 -1.3(3) . . . . ? C24 C23 C28 C27 1.4(2) . . . . ? C5 C23 C28 C27 -179.26(14) . . . . ? C26 C27 C28 C23 0.2(2) . . . . ? C9 C10 C29 C30 -59.3(2) . . . . ? C11 C10 C29 C30 125.82(16) . . . . ? C9 C10 C29 C34 118.68(16) . . . . ? C11 C10 C29 C34 -56.1(2) . . . . ? C34 C29 C30 C31 -1.0(2) . . . . ? C10 C29 C30 C31 177.05(15) . . . . ? C29 C30 C31 C32 1.9(3) . . . . ? C30 C31 C32 C33 -1.2(3) . . . . ? C31 C32 C33 C34 -0.4(3) . . . . ? C32 C33 C34 C29 1.2(3) . . . . ? C30 C29 C34 C33 -0.5(2) . . . . ? C10 C29 C34 C33 -178.62(15) . . . . ? C16 C15 C35 C40 64.1(2) . . . . ? C14 C15 C35 C40 -116.90(17) . . . . ? C16 C15 C35 C36 -114.93(16) . . . . ? C14 C15 C35 C36 64.1(2) . . . . ? C40 C35 C36 C37 -1.1(2) . . . . ? C15 C35 C36 C37 177.91(15) . . . . ? C35 C36 C37 C38 0.1(3) . . . . ? C36 C37 C38 C39 1.0(3) . . . . ? C37 C38 C39 C40 -1.0(3) . . . . ? C38 C39 C40 C35 -0.1(3) . . . . ? C36 C35 C40 C39 1.1(3) . . . . ? C15 C35 C40 C39 -177.91(16) . . . . ? C1 C20 C41 C46 -77.59(19) . . . . ? C19 C20 C41 C46 101.90(17) . . . . ? C1 C20 C41 C42 104.05(17) . . . . ? C19 C20 C41 C42 -76.46(18) . . . . ? C46 C41 C42 C43 -0.6(2) . . . . ? C20 C41 C42 C43 177.77(15) . . . . ? C41 C42 C43 C44 0.3(2) . . . . ? C42 C43 C44 C45 0.5(3) . . . . ? C43 C44 C45 C46 -0.9(3) . . . . ? C42 C41 C46 C45 0.2(2) . . . . ? C20 C41 C46 C45 -178.15(15) . . . . ? C44 C45 C46 C41 0.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N3 0.84 2.36 2.920(2) 124 1_555 N2 H2 N1 0.84 2.51 2.987(2) 117 1_555 N4 H4 N3 0.86 2.29 2.901(3) 128 1_555 N4 H4 N1 0.86 2.54 2.983(2) 113 1_555 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.290 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.041 data_7d _database_code_depnum_ccdc_archive 'CCDC 756651' #TrackingRef 'X-ray_Structures_Chlorins.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H66 N4 O16, 4(C H2 Cl2)' _chemical_formula_sum 'C64 H74 Cl8 N4 O16' _chemical_formula_weight 1438.87 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8723(15) _cell_length_b 12.237(3) _cell_length_c 14.380(2) _cell_angle_alpha 108.550(3) _cell_angle_beta 111.400(2) _cell_angle_gamma 95.110(3) _cell_volume 1642.5(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5103 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 29.09 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 750 _exptl_absorpt_coefficient_mu 0.414 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.852 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 16694 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.28 _reflns_number_total 8035 _reflns_number_gt 6289 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4' _computing_data_reduction 'Apex2 v2008.2-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0442P)^2^+1.5568P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8035 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 C1 C 0.9857(2) 1.21494(17) 0.67893(16) 0.0148(4) Uani 1 1 d . . . C2 C 0.9218(2) 1.25473(18) 0.75872(17) 0.0185(4) Uani 1 1 d . . . H2 H 0.9893 1.2680 0.8329 0.022 Uiso 1 1 calc R . . C3 C 0.8058(2) 1.14631(17) 0.71947(17) 0.0169(4) Uani 1 1 d . . . H3 H 0.8011 1.1262 0.7805 0.020 Uiso 1 1 calc R . . C4 C 0.8457(2) 1.05109(17) 0.64611(16) 0.0153(4) Uani 1 1 d . . . C5 C 0.7842(2) 0.93186(17) 0.61018(16) 0.0146(4) Uani 1 1 d . . . C6 C 0.7945(2) 0.83800(17) 0.52890(16) 0.0151(4) Uani 1 1 d . . . C7 C 0.7236(2) 0.71776(18) 0.48552(17) 0.0177(4) Uani 1 1 d . . . H7 H 0.6641 0.6854 0.5097 0.021 Uiso 1 1 calc R . . C8 C 0.7555(2) 0.65603(18) 0.40267(17) 0.0179(4) Uani 1 1 d . . . H8 H 0.7199 0.5742 0.3584 0.021 Uiso 1 1 calc R . . C9 C 0.8510(2) 0.73576(17) 0.39459(16) 0.0154(4) Uani 1 1 d . . . C10 C 0.9141(2) 0.70749(17) 0.32335(16) 0.0148(4) Uani 1 1 d . . . C11 C 0.8969(3) 1.4379(2) 0.8630(2) 0.0436(8) Uani 1 1 d . . . H11A H 0.8539 1.3958 0.8950 0.065 Uiso 1 1 calc R . . H11B H 0.8566 1.5052 0.8570 0.065 Uiso 1 1 calc R . . H11C H 0.9945 1.4667 0.9089 0.065 Uiso 1 1 calc R . . C12 C 0.5984(2) 1.2058(2) 0.7079(2) 0.0265(5) Uani 1 1 d . . . H12A H 0.5910 1.1606 0.7517 0.040 Uiso 1 1 calc R . . H12B H 0.5075 1.2005 0.6557 0.040 Uiso 1 1 calc R . . H12C H 0.6422 1.2890 0.7548 0.040 Uiso 1 1 calc R . . C13 C 0.7049(2) 0.89905(17) 0.66779(16) 0.0156(4) Uani 1 1 d . . . C14 C 0.5692(2) 0.90423(17) 0.64040(16) 0.0163(4) Uani 1 1 d . . . H14 H 0.5215 0.9249 0.5809 0.020 Uiso 1 1 calc R . . C15 C 0.5040(2) 0.87879(17) 0.70138(16) 0.0154(4) Uani 1 1 d . . . C16 C 0.5739(2) 0.84620(17) 0.78740(16) 0.0159(4) Uani 1 1 d . . . C17 C 0.7091(2) 0.83899(18) 0.81358(16) 0.0171(4) Uani 1 1 d . . . C18 C 0.7747(2) 0.86602(18) 0.75369(17) 0.0170(4) Uani 1 1 d . . . H18 H 0.8669 0.8620 0.7713 0.020 Uiso 1 1 calc R . . C19 C 0.2942(2) 0.9117(2) 0.59607(19) 0.0252(5) Uani 1 1 d . . . H19A H 0.3347 0.9919 0.6064 0.038 Uiso 1 1 calc R . . H19B H 0.2014 0.9079 0.5911 0.038 Uiso 1 1 calc R . . H19C H 0.2919 0.8547 0.5294 0.038 Uiso 1 1 calc R . . C20 C 0.4458(3) 0.7019(2) 0.8100(2) 0.0296(5) Uani 1 1 d . . . H20A H 0.3626 0.6832 0.7446 0.044 Uiso 1 1 calc R . . H20B H 0.4229 0.6859 0.8651 0.044 Uiso 1 1 calc R . . H20C H 0.5071 0.6528 0.7931 0.044 Uiso 1 1 calc R . . C21 C 0.9048(2) 0.7976(3) 0.9281(2) 0.0319(6) Uani 1 1 d . . . H21A H 0.9133 0.7396 0.8669 0.048 Uiso 1 1 calc R . . H21B H 0.9343 0.7724 0.9895 0.048 Uiso 1 1 calc R . . H21C H 0.9619 0.8752 0.9483 0.048 Uiso 1 1 calc R . . C22 C 0.8651(2) 0.58273(17) 0.24085(17) 0.0161(4) Uani 1 1 d . . . C23 C 0.9068(2) 0.48923(18) 0.26976(17) 0.0177(4) Uani 1 1 d . . . H23 H 0.9602 0.5028 0.3431 0.021 Uiso 1 1 calc R . . C24 C 0.8701(2) 0.37600(18) 0.19076(18) 0.0179(4) Uani 1 1 d . . . C25 C 0.7914(2) 0.35471(18) 0.08277(17) 0.0184(4) Uani 1 1 d . . . C26 C 0.7406(2) 0.44717(18) 0.05613(16) 0.0172(4) Uani 1 1 d . . . C27 C 0.7790(2) 0.56098(18) 0.13490(17) 0.0166(4) Uani 1 1 d . . . H27 H 0.7462 0.6237 0.1160 0.020 Uiso 1 1 calc R . . C28 C 0.9681(3) 0.2938(2) 0.3232(2) 0.0311(5) Uani 1 1 d . . . H28A H 1.0582 0.3478 0.3596 0.047 Uiso 1 1 calc R . . H28B H 0.9766 0.2165 0.3280 0.047 Uiso 1 1 calc R . . H28C H 0.9100 0.3267 0.3581 0.047 Uiso 1 1 calc R . . C29 C 0.7087(3) 0.1418(2) 0.0006(2) 0.0298(5) Uani 1 1 d . . . H29A H 0.7806 0.1103 0.0408 0.045 Uiso 1 1 calc R . . H29B H 0.6587 0.0840 -0.0735 0.045 Uiso 1 1 calc R . . H29C H 0.6463 0.1570 0.0356 0.045 Uiso 1 1 calc R . . C30 C 0.6054(2) 0.5098(2) -0.08157(19) 0.0253(5) Uani 1 1 d . . . H30A H 0.5550 0.5456 -0.0402 0.038 Uiso 1 1 calc R . . H30B H 0.5451 0.4770 -0.1587 0.038 Uiso 1 1 calc R . . H30C H 0.6822 0.5703 -0.0677 0.038 Uiso 1 1 calc R . . C31 C 0.6517(3) 0.3930(2) 0.5641(2) 0.0358(6) Uani 1 1 d . . . H31A H 0.6966 0.3514 0.6112 0.043 Uiso 1 1 calc R . . H31B H 0.5604 0.3426 0.5124 0.043 Uiso 1 1 calc R . . C32 C 0.6845(2) 0.9327(2) 0.11572(19) 0.0257(5) Uani 1 1 d . . . H32A H 0.6529 0.9104 0.0369 0.031 Uiso 1 1 calc R . . H32B H 0.6535 1.0048 0.1440 0.031 Uiso 1 1 calc R . . Cl1 Cl 0.74691(7) 0.41350(6) 0.49280(5) 0.03644(16) Uani 1 1 d . . . Cl2 Cl 0.63479(9) 0.52998(7) 0.64394(6) 0.0489(2) Uani 1 1 d . . . Cl3 Cl 0.61207(8) 0.81616(6) 0.14116(7) 0.0462(2) Uani 1 1 d . . . Cl4 Cl 0.86324(7) 0.96409(6) 0.17651(6) 0.04048(17) Uani 1 1 d . . . N1 N 0.93963(17) 1.09723(14) 0.61845(13) 0.0145(3) Uani 1 1 d . . . N2 N 0.87185(17) 0.84500(14) 0.47238(14) 0.0154(3) Uani 1 1 d . . . H2A H 0.9268 0.9101 0.4844 0.018 Uiso 1 1 calc R . . O1 O 0.87617(17) 1.35943(13) 0.75866(14) 0.0263(4) Uani 1 1 d . . . O2 O 0.67773(15) 1.15826(13) 0.65170(12) 0.0201(3) Uani 1 1 d . . . O3 O 0.37351(15) 0.88352(14) 0.68543(12) 0.0201(3) Uani 1 1 d . . . O4 O 0.51111(15) 0.82414(13) 0.84972(12) 0.0202(3) Uani 1 1 d . . . O5 O 0.76610(15) 0.80558(15) 0.89843(13) 0.0243(3) Uani 1 1 d . . . O6 O 0.90923(17) 0.28005(13) 0.21267(13) 0.0232(3) Uani 1 1 d . . . O7 O 0.76756(18) 0.24953(13) -0.00115(13) 0.0270(4) Uani 1 1 d . . . O8 O 0.65460(16) 0.41726(13) -0.04965(12) 0.0216(3) Uani 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 C1 0.0148(9) 0.0163(9) 0.0154(9) 0.0068(8) 0.0077(8) 0.0045(7) C2 0.0217(10) 0.0159(9) 0.0189(10) 0.0047(8) 0.0119(9) 0.0020(8) C3 0.0201(10) 0.0157(9) 0.0178(10) 0.0065(8) 0.0112(8) 0.0025(8) C4 0.0165(9) 0.0172(9) 0.0146(9) 0.0063(8) 0.0086(8) 0.0040(8) C5 0.0141(9) 0.0180(9) 0.0150(9) 0.0078(8) 0.0082(8) 0.0035(7) C6 0.0146(9) 0.0175(9) 0.0182(10) 0.0087(8) 0.0102(8) 0.0045(8) C7 0.0170(10) 0.0173(10) 0.0221(10) 0.0085(8) 0.0112(8) 0.0021(8) C8 0.0191(10) 0.0130(9) 0.0215(10) 0.0049(8) 0.0102(8) 0.0015(8) C9 0.0165(10) 0.0121(9) 0.0177(10) 0.0051(7) 0.0079(8) 0.0031(7) C10 0.0173(10) 0.0127(9) 0.0154(9) 0.0057(7) 0.0077(8) 0.0032(7) C11 0.0380(15) 0.0284(13) 0.0538(18) -0.0109(12) 0.0331(14) -0.0036(11) C12 0.0238(12) 0.0269(12) 0.0328(13) 0.0080(10) 0.0186(10) 0.0074(9) C13 0.0191(10) 0.0122(9) 0.0183(10) 0.0048(7) 0.0118(8) 0.0023(7) C14 0.0184(10) 0.0153(9) 0.0173(10) 0.0064(8) 0.0096(8) 0.0034(8) C15 0.0155(9) 0.0155(9) 0.0171(9) 0.0046(8) 0.0102(8) 0.0038(7) C16 0.0191(10) 0.0161(9) 0.0156(9) 0.0052(8) 0.0115(8) 0.0026(8) C17 0.0192(10) 0.0187(10) 0.0154(9) 0.0068(8) 0.0091(8) 0.0043(8) C18 0.0150(10) 0.0196(10) 0.0200(10) 0.0087(8) 0.0102(8) 0.0041(8) C19 0.0204(11) 0.0362(13) 0.0263(12) 0.0175(10) 0.0113(9) 0.0120(10) C20 0.0357(14) 0.0268(12) 0.0359(13) 0.0151(10) 0.0236(12) 0.0027(10) C21 0.0222(12) 0.0552(16) 0.0327(13) 0.0291(13) 0.0144(11) 0.0175(11) C22 0.0157(9) 0.0148(9) 0.0213(10) 0.0058(8) 0.0125(8) 0.0025(7) C23 0.0183(10) 0.0181(10) 0.0194(10) 0.0067(8) 0.0110(8) 0.0038(8) C24 0.0192(10) 0.0148(9) 0.0271(11) 0.0099(8) 0.0155(9) 0.0058(8) C25 0.0216(10) 0.0133(9) 0.0213(10) 0.0031(8) 0.0138(9) 0.0007(8) C26 0.0163(10) 0.0196(10) 0.0176(10) 0.0063(8) 0.0100(8) 0.0020(8) C27 0.0166(10) 0.0156(9) 0.0203(10) 0.0070(8) 0.0104(8) 0.0038(8) C28 0.0401(15) 0.0252(12) 0.0281(12) 0.0126(10) 0.0108(11) 0.0139(11) C29 0.0340(13) 0.0175(11) 0.0314(13) 0.0043(9) 0.0124(11) -0.0004(9) C30 0.0298(12) 0.0257(11) 0.0231(11) 0.0110(9) 0.0119(10) 0.0082(10) C31 0.0400(15) 0.0275(13) 0.0500(16) 0.0164(12) 0.0279(13) 0.0082(11) C32 0.0277(12) 0.0261(11) 0.0264(12) 0.0114(10) 0.0129(10) 0.0081(9) Cl1 0.0432(4) 0.0331(3) 0.0319(3) 0.0094(3) 0.0185(3) 0.0021(3) Cl2 0.0718(5) 0.0406(4) 0.0475(4) 0.0170(3) 0.0356(4) 0.0256(4) Cl3 0.0637(5) 0.0340(3) 0.0725(5) 0.0301(4) 0.0513(4) 0.0217(3) Cl4 0.0276(3) 0.0331(3) 0.0451(4) 0.0118(3) 0.0010(3) 0.0070(3) N1 0.0153(8) 0.0148(8) 0.0148(8) 0.0065(6) 0.0074(7) 0.0020(6) N2 0.0177(8) 0.0126(8) 0.0188(8) 0.0056(7) 0.0113(7) 0.0022(6) O1 0.0330(9) 0.0143(7) 0.0388(9) 0.0054(7) 0.0267(8) 0.0059(7) O2 0.0198(8) 0.0197(7) 0.0239(8) 0.0073(6) 0.0127(6) 0.0065(6) O3 0.0158(7) 0.0287(8) 0.0211(8) 0.0126(6) 0.0104(6) 0.0070(6) O4 0.0211(8) 0.0248(8) 0.0212(8) 0.0104(6) 0.0147(6) 0.0037(6) O5 0.0179(8) 0.0412(9) 0.0246(8) 0.0215(7) 0.0116(7) 0.0112(7) O6 0.0314(9) 0.0171(7) 0.0250(8) 0.0093(6) 0.0137(7) 0.0102(6) O7 0.0420(10) 0.0148(7) 0.0258(8) 0.0030(6) 0.0205(8) 0.0045(7) O8 0.0249(8) 0.0196(7) 0.0180(7) 0.0059(6) 0.0081(6) 0.0028(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 C1 N1 1.356(3) . ? C1 C10 1.397(3) 2_776 ? C1 C2 1.524(3) . ? C2 O1 1.415(3) . ? C2 C3 1.542(3) . ? C2 H2 1.0000 . ? C3 O2 1.431(3) . ? C3 C4 1.517(3) . ? C3 H3 1.0000 . ? C4 N1 1.362(3) . ? C4 C5 1.392(3) . ? C5 C6 1.401(3) . ? C5 C13 1.503(3) . ? C6 N2 1.380(2) . ? C6 C7 1.418(3) . ? C7 C8 1.373(3) . ? C7 H7 0.9500 . ? C8 C9 1.422(3) . ? C8 H8 0.9500 . ? C9 N2 1.378(2) . ? C9 C10 1.404(3) . ? C10 C1 1.397(3) 2_776 ? C10 C22 1.504(3) . ? C11 O1 1.422(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O2 1.426(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.394(3) . ? C13 C18 1.398(3) . ? C14 C15 1.398(3) . ? C14 H14 0.9500 . ? C15 O3 1.362(2) . ? C15 C16 1.396(3) . ? C16 O4 1.382(2) . ? C16 C17 1.397(3) . ? C17 O5 1.360(2) . ? C17 C18 1.395(3) . ? C18 H18 0.9500 . ? C19 O3 1.429(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O4 1.428(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 O5 1.432(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C27 1.387(3) . ? C22 C23 1.395(3) . ? C23 C24 1.392(3) . ? C23 H23 0.9500 . ? C24 O6 1.373(2) . ? C24 C25 1.395(3) . ? C25 O7 1.380(2) . ? C25 C26 1.402(3) . ? C26 O8 1.367(2) . ? C26 C27 1.394(3) . ? C27 H27 0.9500 . ? C28 O6 1.426(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 O7 1.425(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 O8 1.428(3) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 Cl1 1.754(3) . ? C31 Cl2 1.774(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 Cl4 1.761(2) . ? C32 Cl3 1.770(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? N2 H2A 0.8800 . ? 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 C1 C10 126.06(18) . 2_776 ? N1 C1 C2 111.86(16) . . ? C10 C1 C2 121.95(17) 2_776 . ? O1 C2 C1 112.02(16) . . ? O1 C2 C3 113.24(17) . . ? C1 C2 C3 102.58(16) . . ? O1 C2 H2 109.6 . . ? C1 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? O2 C3 C4 105.79(16) . . ? O2 C3 C2 112.50(16) . . ? C4 C3 C2 101.43(16) . . ? O2 C3 H3 112.2 . . ? C4 C3 H3 112.2 . . ? C2 C3 H3 112.2 . . ? N1 C4 C5 126.64(18) . . ? N1 C4 C3 112.39(17) . . ? C5 C4 C3 120.90(18) . . ? C4 C5 C6 126.31(18) . . ? C4 C5 C13 117.21(17) . . ? C6 C5 C13 116.39(17) . . ? N2 C6 C5 126.80(18) . . ? N2 C6 C7 106.38(17) . . ? C5 C6 C7 126.79(18) . . ? C8 C7 C6 108.48(18) . . ? C8 C7 H7 125.8 . . ? C6 C7 H7 125.8 . . ? C7 C8 C9 108.16(18) . . ? C7 C8 H8 125.9 . . ? C9 C8 H8 125.9 . . ? N2 C9 C10 126.98(18) . . ? N2 C9 C8 106.44(17) . . ? C10 C9 C8 126.55(18) . . ? C1 C10 C9 125.91(18) 2_776 . ? C1 C10 C22 118.12(17) 2_776 . ? C9 C10 C22 115.94(17) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 120.54(18) . . ? C14 C13 C5 122.51(18) . . ? C18 C13 C5 116.93(18) . . ? C13 C14 C15 119.39(19) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? O3 C15 C16 114.45(17) . . ? O3 C15 C14 125.52(18) . . ? C16 C15 C14 120.03(18) . . ? O4 C16 C15 120.22(18) . . ? O4 C16 C17 119.21(18) . . ? C15 C16 C17 120.53(18) . . ? O5 C17 C18 125.42(19) . . ? O5 C17 C16 115.17(18) . . ? C18 C17 C16 119.41(19) . . ? C17 C18 C13 120.08(19) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O5 C21 H21A 109.5 . . ? O5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C27 C22 C23 119.85(18) . . ? C27 C22 C10 119.60(18) . . ? C23 C22 C10 120.54(18) . . ? C24 C23 C22 119.8(2) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? O6 C24 C23 123.19(19) . . ? O6 C24 C25 116.06(18) . . ? C23 C24 C25 120.74(19) . . ? O7 C25 C24 123.70(19) . . ? O7 C25 C26 117.40(19) . . ? C24 C25 C26 118.76(18) . . ? O8 C26 C27 124.12(19) . . ? O8 C26 C25 115.57(18) . . ? C27 C26 C25 120.31(19) . . ? C22 C27 C26 120.14(19) . . ? C22 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? O6 C28 H28A 109.5 . . ? O6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O7 C29 H29A 109.5 . . ? O7 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O7 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O8 C30 H30A 109.5 . . ? O8 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O8 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? Cl1 C31 Cl2 111.62(14) . . ? Cl1 C31 H31A 109.3 . . ? Cl2 C31 H31A 109.3 . . ? Cl1 C31 H31B 109.3 . . ? Cl2 C31 H31B 109.3 . . ? H31A C31 H31B 108.0 . . ? Cl4 C32 Cl3 111.46(13) . . ? Cl4 C32 H32A 109.3 . . ? Cl3 C32 H32A 109.3 . . ? Cl4 C32 H32B 109.3 . . ? Cl3 C32 H32B 109.3 . . ? H32A C32 H32B 108.0 . . ? C1 N1 C4 108.85(16) . . ? C9 N2 C6 110.50(16) . . ? C9 N2 H2A 124.7 . . ? C6 N2 H2A 124.7 . . ? C2 O1 C11 113.3(2) . . ? C12 O2 C3 113.96(17) . . ? C15 O3 C19 117.49(16) . . ? C16 O4 C20 111.90(16) . . ? C17 O5 C21 116.90(17) . . ? C24 O6 C28 117.11(17) . . ? C25 O7 C29 119.03(17) . . ? C26 O8 C30 117.52(16) . . ? 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 O1 -133.61(18) . . . . ? C10 C1 C2 O1 50.3(3) 2_776 . . . ? N1 C1 C2 C3 -11.9(2) . . . . ? C10 C1 C2 C3 172.06(18) 2_776 . . . ? O1 C2 C3 O2 23.9(2) . . . . ? C1 C2 C3 O2 -97.03(19) . . . . ? O1 C2 C3 C4 136.49(17) . . . . ? C1 C2 C3 C4 15.6(2) . . . . ? O2 C3 C4 N1 101.24(19) . . . . ? C2 C3 C4 N1 -16.3(2) . . . . ? O2 C3 C4 C5 -75.9(2) . . . . ? C2 C3 C4 C5 166.48(18) . . . . ? N1 C4 C5 C6 -8.3(3) . . . . ? C3 C4 C5 C6 168.44(19) . . . . ? N1 C4 C5 C13 168.10(19) . . . . ? C3 C4 C5 C13 -15.1(3) . . . . ? C4 C5 C6 N2 3.0(3) . . . . ? C13 C5 C6 N2 -173.49(19) . . . . ? C4 C5 C6 C7 -174.4(2) . . . . ? C13 C5 C6 C7 9.1(3) . . . . ? N2 C6 C7 C8 -1.9(2) . . . . ? C5 C6 C7 C8 175.9(2) . . . . ? C6 C7 C8 C9 1.9(2) . . . . ? C7 C8 C9 N2 -1.2(2) . . . . ? C7 C8 C9 C10 177.1(2) . . . . ? N2 C9 C10 C1 2.5(3) . . . 2_776 ? C8 C9 C10 C1 -175.5(2) . . . 2_776 ? N2 C9 C10 C22 -175.81(19) . . . . ? C8 C9 C10 C22 6.2(3) . . . . ? C4 C5 C13 C14 85.5(2) . . . . ? C6 C5 C13 C14 -97.7(2) . . . . ? C4 C5 C13 C18 -92.5(2) . . . . ? C6 C5 C13 C18 84.3(2) . . . . ? C18 C13 C14 C15 1.5(3) . . . . ? C5 C13 C14 C15 -176.44(18) . . . . ? C13 C14 C15 O3 178.16(19) . . . . ? C13 C14 C15 C16 -1.3(3) . . . . ? O3 C15 C16 O4 -1.3(3) . . . . ? C14 C15 C16 O4 178.22(17) . . . . ? O3 C15 C16 C17 -179.34(18) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? O4 C16 C17 O5 2.4(3) . . . . ? C15 C16 C17 O5 -179.56(18) . . . . ? O4 C16 C17 C18 -177.33(18) . . . . ? C15 C16 C17 C18 0.7(3) . . . . ? O5 C17 C18 C13 179.81(19) . . . . ? C16 C17 C18 C13 -0.5(3) . . . . ? C14 C13 C18 C17 -0.6(3) . . . . ? C5 C13 C18 C17 177.45(18) . . . . ? C1 C10 C22 C27 -75.0(2) 2_776 . . . ? C9 C10 C22 C27 103.5(2) . . . . ? C1 C10 C22 C23 104.2(2) 2_776 . . . ? C9 C10 C22 C23 -77.4(2) . . . . ? C27 C22 C23 C24 4.7(3) . . . . ? C10 C22 C23 C24 -174.47(18) . . . . ? C22 C23 C24 O6 178.85(19) . . . . ? C22 C23 C24 C25 -0.2(3) . . . . ? O6 C24 C25 O7 -8.7(3) . . . . ? C23 C24 C25 O7 170.43(19) . . . . ? O6 C24 C25 C26 175.73(18) . . . . ? C23 C24 C25 C26 -5.2(3) . . . . ? O7 C25 C26 O8 9.7(3) . . . . ? C24 C25 C26 O8 -174.41(18) . . . . ? O7 C25 C26 C27 -169.77(18) . . . . ? C24 C25 C26 C27 6.1(3) . . . . ? C23 C22 C27 C26 -3.7(3) . . . . ? C10 C22 C27 C26 175.42(18) . . . . ? O8 C26 C27 C22 178.86(18) . . . . ? C25 C26 C27 C22 -1.7(3) . . . . ? C10 C1 N1 C4 177.80(19) 2_776 . . . ? C2 C1 N1 C4 1.9(2) . . . . ? C5 C4 N1 C1 -173.4(2) . . . . ? C3 C4 N1 C1 9.6(2) . . . . ? C10 C9 N2 C6 -178.29(19) . . . . ? C8 C9 N2 C6 0.0(2) . . . . ? C5 C6 N2 C9 -176.69(19) . . . . ? C7 C6 N2 C9 1.1(2) . . . . ? C1 C2 O1 C11 -142.52(19) . . . . ? C3 C2 O1 C11 102.1(2) . . . . ? C4 C3 O2 C12 156.37(17) . . . . ? C2 C3 O2 C12 -93.8(2) . . . . ? C16 C15 O3 C19 -177.58(18) . . . . ? C14 C15 O3 C19 2.9(3) . . . . ? C15 C16 O4 C20 91.7(2) . . . . ? C17 C16 O4 C20 -90.2(2) . . . . ? C18 C17 O5 C21 -0.1(3) . . . . ? C16 C17 O5 C21 -179.8(2) . . . . ? C23 C24 O6 C28 12.0(3) . . . . ? C25 C24 O6 C28 -169.0(2) . . . . ? C24 C25 O7 C29 56.3(3) . . . . ? C26 C25 O7 C29 -128.1(2) . . . . ? C27 C26 O8 C30 2.4(3) . . . . ? C25 C26 O8 C30 -177.10(18) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.963 _refine_diff_density_min -0.911 _refine_diff_density_rms 0.065 data_11a _database_code_depnum_ccdc_archive 'CCDC 756652' #TrackingRef 'X-ray_Structures_Chlorins.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H32 N4 O' _chemical_formula_weight 632.74 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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I-42d loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y, -z+3/4' 'x+1/2, -y, -z+3/4' '-y+1/2, -x, z+3/4' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' '-x+1, y+1/2, -z+5/4' 'x+1, -y+1/2, -z+5/4' '-y+1, -x+1/2, z+5/4' 'y+1, x+1/2, z+5/4' _cell_length_a 15.0677(9) _cell_length_b 15.0677(9) _cell_length_c 13.8543(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3145.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4568 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 30.37 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; Friedel pairs were merged prior to refinement. The molecule, while itself asymmetric, is located on a four fold axis and thus disordered. Three pyrrol and two differently oriented dihydropyrrol-ol are disordered with each other in a ratio of 6 to 0.55(1) to 0.45(1). Bond distances within the minor dihydropyrrol-ol sections were restrained to be chemically meaningful. As reference were used the known values found in the related di-hydroxyl compound. sp3-C-O distances were restrained to 1.41(2), sp3-C-sp3-C distances to 1.54(2) and sp2-C-sp3-C distances to 1.52(2) Angstrom. Overlapping carbon atoms and the two oxygen atoms were constrained to have identical ADPs, and the overlapping C atoms were restrained to be approximately isotropic (within a standard deviation of 0.01 squared Angstroms). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13888 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1089 _reflns_number_gt 963 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4 ' _computing_data_reduction 'Apex2 v2008.2-4 ' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0727P)^2^+1.2693P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration unk _refine_ls_number_reflns 1089 _refine_ls_number_parameters 136 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.073 _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 C1 C 0.30064(12) 0.46585(13) 1.01642(17) 0.0356(4) Uani 1 1 d D . . C2 C 0.2380(2) 0.3935(2) 1.0148(4) 0.0387(7) Uani 0.75 1 d PU A 1 H2 H 0.1760 0.3986 1.0259 0.046 Uiso 0.75 1 calc PR A 1 C3 C 0.2821(2) 0.3164(3) 0.9948(3) 0.0415(6) Uani 0.75 1 d PU A 1 H3 H 0.2574 0.2587 0.9883 0.050 Uiso 0.75 1 calc PR A 1 C4 C 0.37429(12) 0.34167(11) 0.98542(15) 0.0333(4) Uani 1 1 d D . . C5 C 0.44405(12) 0.28080(12) 0.97248(16) 0.0332(4) Uani 1 1 d . A . C6 C 0.41891(12) 0.18700(12) 0.94723(16) 0.0338(4) Uani 1 1 d . . . C7 C 0.41598(17) 0.12100(14) 1.01645(19) 0.0488(6) Uani 1 1 d . A . H7 H 0.4313 0.1343 1.0814 0.059 Uiso 1 1 calc R . . C8 C 0.39064(18) 0.03492(14) 0.99143(19) 0.0501(6) Uani 1 1 d . . . H8 H 0.3887 -0.0101 1.0394 0.060 Uiso 1 1 calc R A . C9 C 0.36861(14) 0.01525(13) 0.89807(18) 0.0420(5) Uani 1 1 d . A . H9 H 0.3513 -0.0434 0.8812 0.050 Uiso 1 1 calc R . . C10 C 0.37152(17) 0.08056(15) 0.82842(19) 0.0489(6) Uani 1 1 d . . . H10 H 0.3564 0.0668 0.7636 0.059 Uiso 1 1 calc R A . C11 C 0.39647(15) 0.16627(14) 0.85282(17) 0.0417(5) Uani 1 1 d . A . H11 H 0.3982 0.2110 0.8046 0.050 Uiso 1 1 calc R . . N1 N 0.38295(10) 0.43135(10) 0.99736(14) 0.0323(4) Uani 1 1 d . A . H1 H 0.4327 0.4616 0.9935 0.039 Uiso 0.50 1 calc PR . . C2A C 0.2279(10) 0.4020(9) 1.0420(13) 0.0387(7) Uani 0.138(3) 1 d PD A 2 H2A H 0.1718 0.4122 1.0051 0.046 Uiso 0.138(3) 1 calc PR A 2 C3A C 0.2792(10) 0.3250(11) 1.0078(5) 0.0415(6) Uani 0.138(3) 1 d PD A 2 H3A1 H 0.2502 0.3017 0.9488 0.050 Uiso 0.138(3) 1 calc PR A 2 H3A2 H 0.2759 0.2780 1.0576 0.050 Uiso 0.138(3) 1 calc PR A 2 O1A O 0.2140(9) 0.3812(10) 1.1383(11) 0.084(4) Uani 0.138(3) 1 d PD A 2 H1A H 0.1791 0.3379 1.1423 0.126 Uiso 0.138(3) 1 calc PR A 2 C2B C 0.2282(15) 0.3963(12) 1.025(3) 0.0387(7) Uani 0.112(3) 1 d PD A -3 H2B1 H 0.1766 0.4108 0.9834 0.046 Uiso 0.112(3) 1 calc PR A -3 H2B2 H 0.2082 0.3891 1.0924 0.046 Uiso 0.112(3) 1 calc PR A -3 C3B C 0.2774(12) 0.3136(16) 0.988(2) 0.0415(6) Uani 0.112(3) 1 d PD A -3 H3B H 0.2549 0.2918 0.9247 0.050 Uiso 0.112(3) 1 calc PR A -3 O1B O 0.2554(16) 0.2566(12) 1.0662(16) 0.084(4) Uani 0.112(3) 1 d PD A -3 H1B H 0.2670 0.2820 1.1187 0.126 Uiso 0.112(3) 1 calc PR A -3 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 C1 0.0254(8) 0.0305(9) 0.0510(11) 0.0031(8) 0.0016(9) -0.0012(7) C2 0.0221(11) 0.0319(10) 0.062(2) -0.0078(12) 0.0121(12) -0.0012(8) C3 0.0288(9) 0.0287(10) 0.0669(15) -0.0045(11) 0.0056(11) -0.0037(8) C4 0.0251(8) 0.0252(8) 0.0497(11) -0.0009(8) 0.0017(8) -0.0031(6) C5 0.0292(8) 0.0223(8) 0.0480(10) -0.0015(8) 0.0034(8) -0.0018(7) C6 0.0259(8) 0.0224(8) 0.0530(11) -0.0028(8) 0.0034(8) -0.0012(6) C7 0.0647(15) 0.0306(10) 0.0510(12) 0.0005(9) -0.0007(11) -0.0079(10) C8 0.0610(14) 0.0301(9) 0.0592(13) 0.0049(10) 0.0073(13) -0.0084(9) C9 0.0328(10) 0.0267(9) 0.0665(14) -0.0075(9) 0.0007(10) -0.0046(8) C10 0.0566(14) 0.0341(10) 0.0558(13) -0.0074(10) -0.0030(11) -0.0066(10) C11 0.0444(11) 0.0294(9) 0.0513(12) -0.0009(9) 0.0004(10) -0.0005(8) N1 0.0238(7) 0.0236(7) 0.0494(9) 0.0010(7) 0.0013(7) -0.0004(5) C2A 0.0221(11) 0.0319(10) 0.062(2) -0.0078(12) 0.0121(12) -0.0012(8) C3A 0.0288(9) 0.0287(10) 0.0669(15) -0.0045(11) 0.0056(11) -0.0037(8) O1A 0.077(7) 0.060(6) 0.114(10) 0.016(7) 0.027(8) -0.019(6) C2B 0.0221(11) 0.0319(10) 0.062(2) -0.0078(12) 0.0121(12) -0.0012(8) C3B 0.0288(9) 0.0287(10) 0.0669(15) -0.0045(11) 0.0056(11) -0.0037(8) O1B 0.077(7) 0.060(6) 0.114(10) 0.016(7) 0.027(8) -0.019(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 C1 N1 1.370(2) . ? C1 C5 1.399(3) 3_567 ? C1 C2 1.442(4) . ? C1 C2A 1.500(15) . ? C1 C2B 1.517(17) . ? C2 C3 1.366(4) . ? C2 H2 0.9500 . ? C3 C4 1.447(4) . ? C3 H3 0.9500 . ? C4 N1 1.368(2) . ? C4 C5 1.406(2) . ? C4 C3A 1.488(15) . ? C4 C3B 1.520(18) . ? C5 C1 1.399(3) 4_657 ? C5 C6 1.504(3) . ? C6 C7 1.382(3) . ? C6 C11 1.387(3) . ? C7 C8 1.396(3) . ? C7 H7 0.9500 . ? C8 C9 1.368(4) . ? C8 H8 0.9500 . ? C9 C10 1.379(3) . ? C9 H9 0.9500 . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? N1 H1 0.8800 . ? C2A O1A 1.387(17) . ? C2A C3A 1.473(16) . ? C2A H2A 1.0000 . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? O1A H1A 0.8400 . ? C2B C3B 1.536(19) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B O1B 1.418(19) . ? C3B H3B 1.0000 . ? O1B H1B 0.8400 . ? 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 C1 C5 125.65(16) . 3_567 ? N1 C1 C2 107.61(19) . . ? C5 C1 C2 126.5(2) 3_567 . ? N1 C1 C2A 117.6(6) . . ? C5 C1 C2A 116.1(6) 3_567 . ? N1 C1 C2B 113.8(9) . . ? C5 C1 C2B 120.5(9) 3_567 . ? C3 C2 C1 109.1(3) . . ? C3 C2 H2 125.4 . . ? C1 C2 H2 125.4 . . ? C2 C3 C4 105.2(3) . . ? C2 C3 H3 127.4 . . ? C4 C3 H3 127.4 . . ? N1 C4 C5 126.04(16) . . ? N1 C4 C3 109.9(2) . . ? C5 C4 C3 123.9(2) . . ? N1 C4 C3A 103.5(6) . . ? C5 C4 C3A 129.5(6) . . ? N1 C4 C3B 111.3(10) . . ? C5 C4 C3B 122.7(10) . . ? C1 C5 C4 124.90(16) 4_657 . ? C1 C5 C6 118.08(16) 4_657 . ? C4 C5 C6 117.01(16) . . ? C7 C6 C11 118.98(19) . . ? C7 C6 C5 121.5(2) . . ? C11 C6 C5 119.50(19) . . ? C6 C7 C8 120.3(2) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.2(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 119.96(19) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 120.2(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C6 C11 C10 120.4(2) . . ? C6 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C4 N1 C1 108.17(15) . . ? C4 N1 H1 125.9 . . ? C1 N1 H1 125.9 . . ? O1A C2A C3A 102.1(11) . . ? O1A C2A C1 118.9(14) . . ? C3A C2A C1 92.7(11) . . ? O1A C2A H2A 113.5 . . ? C3A C2A H2A 113.5 . . ? C1 C2A H2A 113.5 . . ? C2A C3A C4 116.0(13) . . ? C2A C3A H3A1 108.3 . . ? C4 C3A H3A1 108.3 . . ? C2A C3A H3A2 108.3 . . ? C4 C3A H3A2 108.3 . . ? H3A1 C3A H3A2 107.4 . . ? C2A O1A H1A 109.5 . . ? C1 C2B C3B 100.8(16) . . ? C1 C2B H2B1 111.6 . . ? C3B C2B H2B1 111.6 . . ? C1 C2B H2B2 111.6 . . ? C3B C2B H2B2 111.6 . . ? H2B1 C2B H2B2 109.4 . . ? O1B C3B C4 114.4(19) . . ? O1B C3B C2B 97.4(16) . . ? C4 C3B C2B 104.3(16) . . ? O1B C3B H3B 113.1 . . ? C4 C3B H3B 113.1 . . ? C2B C3B H3B 113.1 . . ? 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 -0.2(5) . . . . ? C5 C1 C2 C3 175.1(3) 3_567 . . . ? C2A C1 C2 C3 -130(2) . . . . ? C2B C1 C2 C3 -147(11) . . . . ? C1 C2 C3 C4 1.0(5) . . . . ? C2 C3 C4 N1 -1.5(4) . . . . ? C2 C3 C4 C5 174.6(3) . . . . ? C2 C3 C4 C3A 42(4) . . . . ? C2 C3 C4 C3B -114(16) . . . . ? N1 C4 C5 C1 9.7(4) . . . 4_657 ? C3 C4 C5 C1 -165.7(3) . . . 4_657 ? C3A C4 C5 C1 -157.5(5) . . . 4_657 ? C3B C4 C5 C1 -169.9(13) . . . 4_657 ? N1 C4 C5 C6 -171.9(2) . . . . ? C3 C4 C5 C6 12.7(4) . . . . ? C3A C4 C5 C6 20.9(5) . . . . ? C3B C4 C5 C6 8.5(13) . . . . ? C1 C5 C6 C7 79.5(3) 4_657 . . . ? C4 C5 C6 C7 -99.0(2) . . . . ? C1 C5 C6 C11 -101.8(3) 4_657 . . . ? C4 C5 C6 C11 79.7(3) . . . . ? C11 C6 C7 C8 -0.1(3) . . . . ? C5 C6 C7 C8 178.7(2) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 0.1(4) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C7 C6 C11 C10 0.0(3) . . . . ? C5 C6 C11 C10 -178.8(2) . . . . ? C9 C10 C11 C6 0.2(4) . . . . ? C5 C4 N1 C1 -174.6(2) . . . . ? C3 C4 N1 C1 1.4(3) . . . . ? C3A C4 N1 C1 -4.7(4) . . . . ? C3B C4 N1 C1 5.0(12) . . . . ? C5 C1 N1 C4 -176.1(2) 3_567 . . . ? C2 C1 N1 C4 -0.8(3) . . . . ? C2A C1 N1 C4 13.5(8) . . . . ? C2B C1 N1 C4 3.7(17) . . . . ? N1 C1 C2A O1A 90.9(13) . . . . ? C5 C1 C2A O1A -80.4(13) 3_567 . . . ? C2 C1 C2A O1A 147(3) . . . . ? N1 C1 C2A C3A -14.5(12) . . . . ? C5 C1 C2A C3A 174.1(6) 3_567 . . . ? C2 C1 C2A C3A 41.2(17) . . . . ? C2B C1 C2A C3A 55(7) . . . . ? O1A C2A C3A C4 -109.4(11) . . . . ? C1 C2A C3A C4 10.9(12) . . . . ? N1 C4 C3A C2A -4.9(10) . . . . ? C5 C4 C3A C2A 164.4(9) . . . . ? C3 C4 C3A C2A -143(4) . . . . ? N1 C1 C2B C3B -10(3) . . . . ? C5 C1 C2B C3B 169.5(13) 3_567 . . . ? C2 C1 C2B C3B 24(9) . . . . ? N1 C4 C3B O1B -116.5(17) . . . . ? C5 C4 C3B O1B 63(2) . . . . ? C3 C4 C3B O1B -48(15) . . . . ? N1 C4 C3B C2B -11(2) . . . . ? C5 C4 C3B C2B 168.3(16) . . . . ? C3 C4 C3B C2B 57(15) . . . . ? C1 C2B C3B O1B 130(2) . . . . ? C1 C2B C3B C4 12(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.187 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.039