Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _audit_creation_date 2006-06-12 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? _publ_contact_author_name 'Jannie Swarts' _publ_contact_author_address ; Department of Chemistry University of the Free State P.O. Box 339 Bloemfontein 9300 South Africa ; _publ_contact_author_email swartsjc.sci@mail.uovs.ac.za _publ_contact_author_phone '+27-51-401 2781' _publ_contact_author_fax '+27-51-444 6384' _publ_contact_letter ; Date of submission 26 January 2007 Please consider this CIF for pre-pulication deposition as part of a publication in Dalton Transactions. ; _publ_section_title ; Remarkable isolation of scrambling analougues of 5-ferrocenyl-10,20- diphenylporphyrine. Synthesis, structure and electrochemical characterisation. ; loop_ _publ_author_name 'Jannie Swarts' 'Aurelien Auger' 'Alfred J. Muller' data_6iaa1_0x _database_code_depnum_ccdc_archive 'CCDC 635092' _audit_creation_date 2006-06-12T19:42:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety '2(C36 H26 Fe N4), C7 H8' _chemical_formula_sum 'C79 H60 Fe2 N8' _chemical_formula_weight 1233.05 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.4122(4) _cell_length_b 12.0231(3) _cell_length_c 13.4818(3) _cell_angle_alpha 90 _cell_angle_beta 94.5580(10) _cell_angle_gamma 90 _cell_volume 2813.47(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8671 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.28 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1284 _exptl_absorpt_coefficient_mu 0.575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.774 _exptl_absorpt_correction_T_max 0.9036 _exptl_absorpt_process_details ; SADABS (Bruker, 2004) ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_source 'fine-focus sealed tube' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 512 _diffrn_measurement_device_type ; Bruker X8 Apex II Kappa 4K CCD ; _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 64505 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 6993 _reflns_number_gt 6406 _reflns_threshold_expression >2sigma(I) _exptl_special_details ; See manuscript ; #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement 'Saint-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'WinGX (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0487P)^2^+1.7089P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6993 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0891 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.002 _refine_diff_density_max 0.479 _refine_diff_density_min -0.281 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Fe Fe 0.827619(10) 0.623812(15) 0.458770(13) 0.01246(6) Uani 1 d . . . N1 N 0.54609(6) 0.53226(9) 0.38824(8) 0.0134(2) Uani 1 d . . . N2 N 0.38416(6) 0.55832(9) 0.28584(8) 0.0134(2) Uani 1 d . . . N3 N 0.36103(6) 0.75512(9) 0.38738(8) 0.0129(2) Uani 1 d . . . N4 N 0.52504(6) 0.73310(9) 0.48224(8) 0.0131(2) Uani 1 d . . . C1 C 0.64659(7) 0.62705(10) 0.49551(9) 0.0131(2) Uani 1 d . . . C2 C 0.61937(7) 0.53862(10) 0.43403(9) 0.0137(2) Uani 1 d . . . C3 C 0.65852(7) 0.43936(11) 0.40768(10) 0.0164(2) Uani 1 d . . . H3 H 0.7104 0.4206 0.4278 0.02 Uiso 1 calc R . . C4 C 0.60819(8) 0.37652(10) 0.34865(10) 0.0161(2) Uani 1 d . . . H4 H 0.6186 0.3055 0.3219 0.019 Uiso 1 calc R . . C5 C 0.53719(7) 0.43577(10) 0.33408(9) 0.0140(2) Uani 1 d . . . C6 C 0.47391(7) 0.40216(10) 0.27224(9) 0.0148(2) Uani 1 d . . . H6 H 0.4787 0.332 0.2408 0.018 Uiso 1 calc R . . C7 C 0.40426(7) 0.45723(10) 0.24991(9) 0.0141(2) Uani 1 d . . . C8 C 0.34309(8) 0.41221(11) 0.18178(10) 0.0163(2) Uani 1 d . . . H8 H 0.3433 0.3431 0.1477 0.02 Uiso 1 calc R . . C9 C 0.28583(7) 0.48832(11) 0.17658(9) 0.0158(2) Uani 1 d . . . H9 H 0.2378 0.4833 0.1381 0.019 Uiso 1 calc R . . C10 C 0.31220(7) 0.57937(10) 0.24161(9) 0.0134(2) Uani 1 d . . . C11 C 0.26869(7) 0.67474(10) 0.25972(9) 0.0132(2) Uani 1 d . . . C12 C 0.29274(7) 0.75693(10) 0.32891(9) 0.0127(2) Uani 1 d . . . C13 C 0.25524(7) 0.85923(11) 0.34964(9) 0.0144(2) Uani 1 d . . . H13 H 0.2069 0.8838 0.32 0.017 Uiso 1 calc R . . C14 C 0.30131(7) 0.91533(11) 0.41960(10) 0.0150(2) Uani 1 d . . . H14 H 0.2904 0.9857 0.4473 0.018 Uiso 1 calc R . . C15 C 0.36873(7) 0.85009(10) 0.44383(9) 0.0134(2) Uani 1 d . . . C16 C 0.42979(7) 0.87839(10) 0.51185(10) 0.0142(2) Uani 1 d . . . H16 H 0.4228 0.9436 0.5499 0.017 Uiso 1 calc R . . C17 C 0.49967(7) 0.82368(10) 0.53139(9) 0.0137(2) Uani 1 d . . . C18 C 0.55702(7) 0.86113(11) 0.60838(10) 0.0152(2) Uani 1 d . . . H18 H 0.5524 0.9216 0.6529 0.018 Uiso 1 calc R . . C19 C 0.61819(7) 0.79281(11) 0.60401(9) 0.0149(2) Uani 1 d . . . H19 H 0.6651 0.7956 0.645 0.018 Uiso 1 calc R . . C20 C 0.59794(7) 0.71387(10) 0.52393(9) 0.0131(2) Uani 1 d . . . C21 C 0.19473(7) 0.69517(10) 0.19885(9) 0.0136(2) Uani 1 d . . . C22 C 0.19560(7) 0.71386(11) 0.09677(10) 0.0161(2) Uani 1 d . . . H22 H 0.2426 0.7077 0.0659 0.019 Uiso 1 calc R . . C23 C 0.12809(8) 0.74144(12) 0.03999(10) 0.0195(3) Uani 1 d . . . H23 H 0.1292 0.7535 -0.0295 0.023 Uiso 1 calc R . . C24 C 0.05925(8) 0.75148(12) 0.08413(10) 0.0203(3) Uani 1 d . . . H24 H 0.0136 0.7726 0.0455 0.024 Uiso 1 calc R . . C25 C 0.05738(8) 0.73056(12) 0.18492(11) 0.0203(3) Uani 1 d . . . H25 H 0.0101 0.7358 0.2152 0.024 Uiso 1 calc R . . C26 C 0.12460(8) 0.70193(12) 0.24188(10) 0.0178(3) Uani 1 d . . . H26 H 0.1227 0.6868 0.3108 0.021 Uiso 1 calc R . . C27 C 0.72862(7) 0.63223(11) 0.53437(9) 0.0143(2) Uani 1 d . . . C28 C 0.77276(7) 0.73322(11) 0.54373(9) 0.0161(2) Uani 1 d . . . H28 H 0.7551 0.8049 0.5228 0.019 Uiso 1 calc R . . C29 C 0.84722(8) 0.70816(13) 0.58952(10) 0.0191(3) Uani 1 d . . . H29 H 0.8875 0.76 0.6053 0.023 Uiso 1 calc R . . C30 C 0.85059(8) 0.59164(13) 0.60737(10) 0.0200(3) Uani 1 d . . . H30 H 0.8937 0.5521 0.6371 0.024 Uiso 1 calc R . . C31 C 0.77828(7) 0.54446(12) 0.57310(9) 0.0173(3) Uani 1 d . . . H31 H 0.7651 0.4679 0.5755 0.021 Uiso 1 calc R . . C32 C 0.79574(8) 0.59463(12) 0.31134(9) 0.0176(3) Uani 1 d . . . H32 H 0.7448 0.5831 0.2824 0.021 Uiso 1 calc R . . C33 C 0.83388(8) 0.69908(12) 0.32325(10) 0.0198(3) Uani 1 d . . . H33 H 0.8129 0.7694 0.3039 0.024 Uiso 1 calc R . . C34 C 0.90921(8) 0.67934(13) 0.36932(10) 0.0208(3) Uani 1 d . . . H34 H 0.9473 0.7343 0.3859 0.025 Uiso 1 calc R . . C35 C 0.91733(8) 0.56287(13) 0.38611(10) 0.0206(3) Uani 1 d . . . H35 H 0.9618 0.5265 0.416 0.025 Uiso 1 calc R . . C36 C 0.84719(8) 0.51048(12) 0.35023(10) 0.0189(3) Uani 1 d . . . H36 H 0.8366 0.433 0.352 0.023 Uiso 1 calc R . . C01 C 0.0330(10) 0.5294(15) -0.1544(13) 0.036(2) Uani 0.5 d P -1 A H01A H -0.0132 0.5234 -0.2006 0.053 Uiso 0.5 calc PR -1 A H01B H 0.0708 0.4735 -0.1712 0.053 Uiso 0.5 calc PR -1 A H01C H 0.0553 0.6038 -0.1595 0.053 Uiso 0.5 calc PR -1 A C02 C 0.01126(18) 0.5101(2) -0.0479(2) 0.0231(6) Uani 0.5 d P -1 A C03 C -0.0598(8) 0.5320(12) -0.0232(10) 0.044(4) Uani 0.5 d P -1 A H03 H -0.0966 0.5606 -0.0725 0.053 Uiso 0.5 calc PR -1 A C04 C -0.0823(2) 0.5140(3) 0.0749(4) 0.0450(11) Uani 0.5 d P -1 A H04 H -0.1332 0.5285 0.0919 0.054 Uiso 0.5 calc PR -1 A C05 C -0.0288(11) 0.4762(14) 0.1405(15) 0.048(4) Uani 0.5 d P -1 A H05 H -0.0429 0.4629 0.2061 0.058 Uiso 0.5 calc PR -1 A C06 C 0.0459(3) 0.4547(3) 0.1213(3) 0.0357(8) Uani 0.5 d P -1 A H06 H 0.0823 0.4289 0.1722 0.043 Uiso 0.5 calc PR -1 A C07 C 0.0668(7) 0.4718(9) 0.0249(5) 0.0175(17) Uani 0.5 d P -1 A H07 H 0.118 0.4577 0.0088 0.021 Uiso 0.5 calc PR -1 A H1 H 0.5144(11) 0.5830(17) 0.3925(14) 0.026(5) Uiso 1 d . . . H2 H 0.3946(12) 0.7034(18) 0.3875(15) 0.030(5) Uiso 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 Fe 0.01165(10) 0.01531(10) 0.01042(10) -0.00021(6) 0.00086(6) 0.00059(6) N1 0.0134(5) 0.0119(5) 0.0150(5) -0.0017(4) 0.0018(4) 0.0013(4) N2 0.0146(5) 0.0122(5) 0.0135(5) -0.0002(4) 0.0014(4) 0.0000(4) N3 0.0131(5) 0.0119(5) 0.0135(5) -0.0008(4) -0.0001(4) 0.0015(4) N4 0.0133(5) 0.0120(5) 0.0140(5) -0.0005(4) 0.0012(4) 0.0008(4) C1 0.0123(5) 0.0143(6) 0.0129(5) 0.0012(4) 0.0015(4) 0.0001(4) C2 0.0132(5) 0.0135(6) 0.0148(6) 0.0008(4) 0.0033(4) 0.0009(4) C3 0.0144(6) 0.0145(6) 0.0205(6) -0.0002(5) 0.0035(5) 0.0023(5) C4 0.0158(6) 0.0135(6) 0.0195(6) -0.0007(4) 0.0044(5) 0.0020(4) C5 0.0158(6) 0.0117(5) 0.0150(6) 0.0003(4) 0.0046(4) 0.0004(4) C6 0.0181(6) 0.0113(5) 0.0153(6) -0.0016(4) 0.0037(5) -0.0005(4) C7 0.0167(6) 0.0127(5) 0.0130(5) -0.0001(4) 0.0021(4) -0.0022(4) C8 0.0189(6) 0.0141(6) 0.0158(6) -0.0022(5) 0.0001(5) -0.0027(5) C9 0.0169(6) 0.0155(6) 0.0149(6) -0.0012(5) -0.0001(4) -0.0031(5) C10 0.0147(5) 0.0140(6) 0.0115(5) 0.0011(4) 0.0015(4) -0.0025(4) C11 0.0130(5) 0.0150(6) 0.0116(5) 0.0023(4) 0.0011(4) -0.0008(4) C12 0.0130(5) 0.0135(5) 0.0119(5) 0.0019(4) 0.0016(4) 0.0002(4) C13 0.0137(5) 0.0149(6) 0.0146(6) 0.0017(4) 0.0018(4) 0.0021(4) C14 0.0150(6) 0.0135(6) 0.0168(6) 0.0000(5) 0.0020(5) 0.0023(4) C15 0.0140(5) 0.0117(5) 0.0149(6) -0.0004(4) 0.0023(4) 0.0009(4) C16 0.0157(6) 0.0120(5) 0.0150(6) -0.0026(4) 0.0013(5) 0.0004(4) C17 0.0147(6) 0.0124(5) 0.0139(5) -0.0006(4) 0.0012(4) -0.0012(4) C18 0.0161(6) 0.0146(6) 0.0148(6) -0.0029(4) 0.0005(5) -0.0006(4) C19 0.0146(6) 0.0163(6) 0.0137(6) -0.0018(5) 0.0005(4) -0.0007(4) C20 0.0131(5) 0.0137(5) 0.0125(5) 0.0010(4) 0.0012(4) -0.0009(4) C21 0.0142(6) 0.0129(5) 0.0135(6) -0.0008(4) -0.0002(4) -0.0007(4) C22 0.0168(6) 0.0167(6) 0.0149(6) -0.0002(5) 0.0018(5) 0.0002(5) C23 0.0226(7) 0.0219(6) 0.0135(6) 0.0017(5) -0.0017(5) -0.0005(5) C24 0.0172(6) 0.0208(6) 0.0217(6) -0.0015(5) -0.0051(5) 0.0003(5) C25 0.0135(6) 0.0253(7) 0.0222(7) -0.0049(5) 0.0017(5) -0.0012(5) C26 0.0170(6) 0.0235(7) 0.0130(6) -0.0012(5) 0.0018(5) -0.0017(5) C27 0.0133(6) 0.0180(6) 0.0115(5) -0.0006(4) 0.0014(4) 0.0009(4) C28 0.0143(6) 0.0187(6) 0.0154(6) -0.0042(5) 0.0016(4) 0.0006(5) C29 0.0143(6) 0.0285(7) 0.0145(6) -0.0070(5) 0.0007(5) -0.0006(5) C30 0.0157(6) 0.0325(7) 0.0117(6) 0.0017(5) 0.0002(5) 0.0048(5) C31 0.0170(6) 0.0216(6) 0.0136(6) 0.0039(5) 0.0034(5) 0.0036(5) C32 0.0184(6) 0.0233(6) 0.0111(6) -0.0006(5) 0.0006(5) -0.0005(5) C33 0.0246(7) 0.0209(6) 0.0141(6) 0.0028(5) 0.0038(5) -0.0009(5) C34 0.0188(6) 0.0284(7) 0.0160(6) -0.0014(5) 0.0059(5) -0.0058(5) C35 0.0166(6) 0.0301(7) 0.0154(6) -0.0028(5) 0.0035(5) 0.0040(5) C36 0.0228(6) 0.0193(6) 0.0148(6) -0.0035(5) 0.0033(5) 0.0020(5) C01 0.062(4) 0.033(4) 0.014(3) 0.006(2) 0.014(3) -0.018(3) C02 0.0272(15) 0.0189(13) 0.0231(15) 0.0013(11) 0.0006(12) -0.0095(11) C03 0.031(5) 0.018(4) 0.082(8) 0.002(3) -0.008(4) -0.006(3) C04 0.0355(19) 0.0162(15) 0.088(3) -0.0077(18) 0.037(2) -0.0070(13) C05 0.089(7) 0.026(4) 0.034(7) -0.006(4) 0.031(4) -0.017(4) C06 0.063(2) 0.0194(15) 0.0235(16) -0.0010(12) -0.0014(16) 0.0011(15) C07 0.013(2) 0.018(4) 0.022(3) -0.001(2) 0.0003(18) 0.000(2) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 C5 1.3729(16) . ? N1 C2 1.3746(16) . ? N1 H1 0.83(2) . ? N2 C7 1.3642(16) . ? N2 C10 1.3679(16) . ? N3 C15 1.3729(16) . ? N3 C12 1.3736(16) . ? N3 H2 0.85(2) . ? N4 C17 1.3664(16) . ? N4 C20 1.3665(16) . ? C1 C2 1.4070(17) . ? C1 C20 1.4162(17) . ? C1 C27 1.4831(17) . ? C2 C3 1.4331(17) . ? C3 C4 1.3643(18) . ? C3 H3 0.95 . ? C4 C5 1.4267(17) . ? C4 H4 0.95 . ? C5 C6 1.3880(18) . ? C6 C7 1.3935(18) . ? C6 H6 0.95 . ? C7 C8 1.4545(17) . ? C8 C9 1.3510(19) . ? C8 H8 0.95 . ? C9 C10 1.4539(17) . ? C9 H9 0.95 . ? C10 C11 1.4063(17) . ? C11 C12 1.4000(17) . ? C11 C21 1.4914(17) . ? C12 C13 1.4305(17) . ? C13 C14 1.3667(18) . ? C13 H13 0.95 . ? C14 C15 1.4281(17) . ? C14 H14 0.95 . ? C15 C16 1.3899(17) . ? C16 C17 1.3898(17) . ? C16 H16 0.95 . ? C17 C18 1.4534(17) . ? C18 C19 1.3500(18) . ? C18 H18 0.95 . ? C19 C20 1.4595(17) . ? C19 H19 0.95 . ? C21 C26 1.3954(17) . ? C21 C22 1.3956(17) . ? C22 C23 1.3909(18) . ? C22 H22 0.95 . ? C23 C24 1.385(2) . ? C23 H23 0.95 . ? C24 C25 1.385(2) . ? C24 H24 0.95 . ? C25 C26 1.3911(19) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C27 C31 1.4361(18) . ? C27 C28 1.4372(18) . ? C28 C29 1.4233(18) . ? C28 H28 0.95 . ? C29 C30 1.422(2) . ? C29 H29 0.95 . ? C30 C31 1.4240(19) . ? C30 H30 0.95 . ? C31 H31 0.95 . ? C32 C36 1.4235(19) . ? C32 C33 1.4236(19) . ? C32 H32 0.95 . ? C33 C34 1.426(2) . ? C33 H33 0.95 . ? C34 C35 1.424(2) . ? C34 H34 0.95 . ? C35 C36 1.4242(19) . ? C35 H35 0.95 . ? C36 H36 0.95 . ? C01 C02 1.531(19) . ? C01 H01A 0.98 . ? C01 H01B 0.98 . ? C01 H01C 0.98 . ? C02 C03 1.332(14) . ? C02 C07 1.401(11) . ? C03 C04 1.425(13) . ? C03 H03 0.95 . ? C04 C05 1.314(19) . ? C04 H04 0.95 . ? C05 C06 1.37(2) . ? C05 H05 0.95 . ? C06 C07 1.392(8) . ? C06 H06 0.95 . ? C07 H07 0.95 . ? 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 C5 N1 C2 110.33(11) . . ? C5 N1 H1 127.7(13) . . ? C2 N1 H1 121.9(13) . . ? C7 N2 C10 105.19(10) . . ? C15 N3 C12 110.30(10) . . ? C15 N3 H2 124.7(13) . . ? C12 N3 H2 125.0(13) . . ? C17 N4 C20 105.12(10) . . ? C2 C1 C20 122.38(11) . . ? C2 C1 C27 120.65(11) . . ? C20 C1 C27 116.97(11) . . ? N1 C2 C1 124.32(11) . . ? N1 C2 C3 106.57(11) . . ? C1 C2 C3 129.10(12) . . ? C4 C3 C2 108.04(11) . . ? C4 C3 H3 126 . . ? C2 C3 H3 126 . . ? C3 C4 C5 108.25(11) . . ? C3 C4 H4 125.9 . . ? C5 C4 H4 125.9 . . ? N1 C5 C6 128.03(12) . . ? N1 C5 C4 106.78(11) . . ? C6 C5 C4 125.11(12) . . ? C5 C6 C7 128.84(12) . . ? C5 C6 H6 115.6 . . ? C7 C6 H6 115.6 . . ? N2 C7 C6 126.15(12) . . ? N2 C7 C8 111.11(11) . . ? C6 C7 C8 122.73(12) . . ? C9 C8 C7 106.32(11) . . ? C9 C8 H8 126.8 . . ? C7 C8 H8 126.8 . . ? C8 C9 C10 106.40(11) . . ? C8 C9 H9 126.8 . . ? C10 C9 H9 126.8 . . ? N2 C10 C11 124.24(11) . . ? N2 C10 C9 110.97(11) . . ? C11 C10 C9 124.75(11) . . ? C12 C11 C10 123.67(11) . . ? C12 C11 C21 116.74(11) . . ? C10 C11 C21 119.49(11) . . ? N3 C12 C11 124.80(11) . . ? N3 C12 C13 106.81(11) . . ? C11 C12 C13 128.32(11) . . ? C14 C13 C12 107.89(11) . . ? C14 C13 H13 126.1 . . ? C12 C13 H13 126.1 . . ? C13 C14 C15 108.27(11) . . ? C13 C14 H14 125.9 . . ? C15 C14 H14 125.9 . . ? N3 C15 C16 127.25(11) . . ? N3 C15 C14 106.72(11) . . ? C16 C15 C14 126.03(12) . . ? C17 C16 C15 128.42(12) . . ? C17 C16 H16 115.8 . . ? C15 C16 H16 115.8 . . ? N4 C17 C16 126.67(11) . . ? N4 C17 C18 111.28(11) . . ? C16 C17 C18 122.03(11) . . ? C19 C18 C17 106.27(11) . . ? C19 C18 H18 126.9 . . ? C17 C18 H18 126.9 . . ? C18 C19 C20 106.43(11) . . ? C18 C19 H19 126.8 . . ? C20 C19 H19 126.8 . . ? N4 C20 C1 124.71(11) . . ? N4 C20 C19 110.87(11) . . ? C1 C20 C19 124.39(11) . . ? C26 C21 C22 118.62(12) . . ? C26 C21 C11 121.78(11) . . ? C22 C21 C11 119.51(11) . . ? C23 C22 C21 120.41(12) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 120.44(12) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 119.62(12) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.15(12) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 120.70(12) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C31 C27 C28 106.66(11) . . ? C31 C27 C1 129.25(12) . . ? C28 C27 C1 124.04(11) . . ? C29 C28 C27 108.75(12) . . ? C29 C28 H28 125.6 . . ? C27 C28 H28 125.6 . . ? C30 C29 C28 107.82(12) . . ? C30 C29 H29 126.1 . . ? C28 C29 H29 126.1 . . ? C29 C30 C31 108.30(12) . . ? C29 C30 H30 125.8 . . ? C31 C30 H30 125.8 . . ? C30 C31 C27 108.45(12) . . ? C30 C31 H31 125.8 . . ? C27 C31 H31 125.8 . . ? C36 C32 C33 108.13(12) . . ? C36 C32 H32 125.9 . . ? C33 C32 H32 125.9 . . ? C32 C33 C34 107.88(12) . . ? C32 C33 H33 126.1 . . ? C34 C33 H33 126.1 . . ? C35 C34 C33 108.02(12) . . ? C35 C34 H34 126 . . ? C33 C34 H34 126 . . ? C34 C35 C36 108.02(12) . . ? C34 C35 H35 126 . . ? C36 C35 H35 126 . . ? C32 C36 C35 107.96(12) . . ? C32 C36 H36 126 . . ? C35 C36 H36 126 . . ? C03 C02 C07 119.5(8) . . ? C03 C02 C01 120.6(9) . . ? C07 C02 C01 119.9(8) . . ? C02 C03 C04 122.1(11) . . ? C02 C03 H03 118.9 . . ? C04 C03 H03 118.9 . . ? C05 C04 C03 116.4(12) . . ? C05 C04 H04 121.8 . . ? C03 C04 H04 121.8 . . ? C04 C05 C06 124.8(17) . . ? C04 C05 H05 117.6 . . ? C06 C05 H05 117.6 . . ? C05 C06 C07 118.1(10) . . ? C05 C06 H06 120.9 . . ? C07 C06 H06 120.9 . . ? C06 C07 C02 119.1(8) . . ? C06 C07 H07 120.5 . . ? C02 C07 H07 120.5 . . ? 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 C5 N1 C2 C1 -179.58(12) . . . . ? C5 N1 C2 C3 -0.61(14) . . . . ? C20 C1 C2 N1 6.28(19) . . . . ? C27 C1 C2 N1 -174.31(11) . . . . ? C20 C1 C2 C3 -172.44(12) . . . . ? C27 C1 C2 C3 7.0(2) . . . . ? N1 C2 C3 C4 -0.68(14) . . . . ? C1 C2 C3 C4 178.22(13) . . . . ? C2 C3 C4 C5 1.65(15) . . . . ? C2 N1 C5 C6 -175.30(12) . . . . ? C2 N1 C5 C4 1.60(14) . . . . ? C3 C4 C5 N1 -2.01(15) . . . . ? C3 C4 C5 C6 175.01(12) . . . . ? N1 C5 C6 C7 -0.1(2) . . . . ? C4 C5 C6 C7 -176.45(13) . . . . ? C10 N2 C7 C6 178.43(12) . . . . ? C10 N2 C7 C8 -0.62(14) . . . . ? C5 C6 C7 N2 0.0(2) . . . . ? C5 C6 C7 C8 178.92(13) . . . . ? N2 C7 C8 C9 0.44(15) . . . . ? C6 C7 C8 C9 -178.64(12) . . . . ? C7 C8 C9 C10 -0.08(14) . . . . ? C7 N2 C10 C11 178.44(12) . . . . ? C7 N2 C10 C9 0.57(13) . . . . ? C8 C9 C10 N2 -0.31(15) . . . . ? C8 C9 C10 C11 -178.17(12) . . . . ? N2 C10 C11 C12 -3.09(19) . . . . ? C9 C10 C11 C12 174.49(12) . . . . ? N2 C10 C11 C21 173.13(11) . . . . ? C9 C10 C11 C21 -9.29(18) . . . . ? C15 N3 C12 C11 177.32(12) . . . . ? C15 N3 C12 C13 0.10(14) . . . . ? C10 C11 C12 N3 -0.05(19) . . . . ? C21 C11 C12 N3 -176.36(11) . . . . ? C10 C11 C12 C13 176.55(12) . . . . ? C21 C11 C12 C13 0.24(19) . . . . ? N3 C12 C13 C14 -0.28(14) . . . . ? C11 C12 C13 C14 -177.37(12) . . . . ? C12 C13 C14 C15 0.35(14) . . . . ? C12 N3 C15 C16 179.96(12) . . . . ? C12 N3 C15 C14 0.11(14) . . . . ? C13 C14 C15 N3 -0.29(14) . . . . ? C13 C14 C15 C16 179.86(13) . . . . ? N3 C15 C16 C17 6.9(2) . . . . ? C14 C15 C16 C17 -173.26(13) . . . . ? C20 N4 C17 C16 176.51(12) . . . . ? C20 N4 C17 C18 -1.73(14) . . . . ? C15 C16 C17 N4 4.6(2) . . . . ? C15 C16 C17 C18 -177.33(13) . . . . ? N4 C17 C18 C19 0.99(15) . . . . ? C16 C17 C18 C19 -177.35(12) . . . . ? C17 C18 C19 C20 0.15(14) . . . . ? C17 N4 C20 C1 -179.95(12) . . . . ? C17 N4 C20 C19 1.82(14) . . . . ? C2 C1 C20 N4 -12.42(19) . . . . ? C27 C1 C20 N4 168.15(11) . . . . ? C2 C1 C20 C19 165.58(12) . . . . ? C27 C1 C20 C19 -13.85(18) . . . . ? C18 C19 C20 N4 -1.26(15) . . . . ? C18 C19 C20 C1 -179.49(12) . . . . ? C12 C11 C21 C26 -64.26(16) . . . . ? C10 C11 C21 C26 119.27(14) . . . . ? C12 C11 C21 C22 112.35(13) . . . . ? C10 C11 C21 C22 -64.12(16) . . . . ? C26 C21 C22 C23 1.63(19) . . . . ? C11 C21 C22 C23 -175.09(12) . . . . ? C21 C22 C23 C24 0.5(2) . . . . ? C22 C23 C24 C25 -2.0(2) . . . . ? C23 C24 C25 C26 1.4(2) . . . . ? C24 C25 C26 C21 0.8(2) . . . . ? C22 C21 C26 C25 -2.2(2) . . . . ? C11 C21 C26 C25 174.40(13) . . . . ? C2 C1 C27 C31 -41.53(19) . . . . ? C20 C1 C27 C31 137.91(13) . . . . ? C2 C1 C27 C28 141.46(13) . . . . ? C20 C1 C27 C28 -39.10(18) . . . . ? C31 C27 C28 C29 -1.42(14) . . . . ? C1 C27 C28 C29 176.17(12) . . . . ? C27 C28 C29 C30 1.02(15) . . . . ? C28 C29 C30 C31 -0.22(15) . . . . ? C29 C30 C31 C27 -0.67(15) . . . . ? C28 C27 C31 C30 1.28(14) . . . . ? C1 C27 C31 C30 -176.14(12) . . . . ? C36 C32 C33 C34 0.20(15) . . . . ? C32 C33 C34 C35 -0.22(15) . . . . ? C33 C34 C35 C36 0.15(15) . . . . ? C33 C32 C36 C35 -0.11(15) . . . . ? C34 C35 C36 C32 -0.03(15) . . . . ? C07 C02 C03 C04 -2.3(19) . . . . ? C01 C02 C03 C04 179.3(10) . . . . ? C02 C03 C04 C05 1.1(16) . . . . ? C03 C04 C05 C06 0.7(18) . . . . ? C04 C05 C06 C07 -1.3(18) . . . . ? C05 C06 C07 C02 0.1(13) . . . . ? C03 C02 C07 C06 1.7(17) . . . . ? C01 C02 C07 C06 -180.0(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 N4 . 0.83(2) 2.17(2) 2.7650(15) 128.5(17) N1 H1 N2 . 0.83(2) 2.604(19) 3.0554(15) 115.7(16) N3 H2 N2 . 0.85(2) 2.22(2) 2.7790(15) 123.4(17) N3 H2 N4 . 0.85(2) 2.54(2) 3.0463(15) 118.8(16)