# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Alajarin, Mateo' 'Bonillo, Baltasar' 'Ortin, Maria-Mar' 'Sanchez-Andrada, Pilar' 'Vidal, Angel' 'Orenes, Raul-Angel' _publ_contact_author_name 'Alajarin, Mateo' _publ_contact_author_email alajarin@um.es _publ_section_title ; Domino Reactions Initiated by Intramolecular Hydride Transfers from Tri(di)arylmethane Fragments to Ketenimine and Carbodiimide Functions ; # Attachment '- Alajarin.cif' data_vidal2s_compound_13e _database_code_depnum_ccdc_archive 'CCDC 779905' #TrackingRef '- Alajarin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H33 N3' _chemical_formula_weight 459.61 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8211(7) _cell_length_b 14.9825(12) _cell_length_c 21.5278(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.0260(10) _cell_angle_gamma 90.00 _cell_volume 2516.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5719 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9838 _exptl_absorpt_correction_T_max 0.9943 _exptl_absorpt_process_details SADABS _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 SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28728 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 28.21 _reflns_number_total 5873 _reflns_number_gt 5109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0446P)^2^+1.4568P] 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 'Me rigid, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5873 _refine_ls_number_parameters 321 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.124 _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 0.99659(17) 0.28873(9) 0.12635(6) 0.0186(3) Uani 1 1 d . . . N2 N 0.8093(2) 0.53568(10) 0.46157(6) 0.0241(3) Uani 1 1 d . . . N3 N 0.48024(18) 0.64746(9) 0.02111(6) 0.0198(3) Uani 1 1 d . . . C1 C 0.7572(2) 0.32900(10) 0.19135(7) 0.0142(3) Uani 1 1 d . . . C2 C 0.5977(2) 0.30496(10) 0.21117(7) 0.0168(3) Uani 1 1 d . . . H2 H 0.5383 0.3455 0.2359 0.020 Uiso 1 1 calc R . . C3 C 0.5238(2) 0.22289(11) 0.19551(8) 0.0198(3) Uani 1 1 d . . . H3 H 0.4156 0.2076 0.2100 0.024 Uiso 1 1 calc R . . C4 C 0.6079(2) 0.16327(11) 0.15876(8) 0.0208(4) Uani 1 1 d . . . H4 H 0.5590 0.1066 0.1488 0.025 Uiso 1 1 calc R . . C5 C 0.7636(2) 0.18725(11) 0.13682(8) 0.0196(3) Uani 1 1 d . . . H5 H 0.8206 0.1472 0.1110 0.023 Uiso 1 1 calc R . . C6 C 0.8378(2) 0.26984(10) 0.15228(7) 0.0162(3) Uani 1 1 d . . . C7 C 1.0827(2) 0.35501(11) 0.14874(7) 0.0171(3) Uani 1 1 d . . . H7 H 1.1867 0.3675 0.1301 0.020 Uiso 1 1 calc R . . C8 C 1.03933(19) 0.41628(10) 0.20142(7) 0.0151(3) Uani 1 1 d . . . C9 C 0.83669(19) 0.42098(10) 0.20657(7) 0.0129(3) Uani 1 1 d . . . C11 C 1.13281(19) 0.37439(11) 0.26042(7) 0.0154(3) Uani 1 1 d D . . C12 C 1.1175(2) 0.28368(11) 0.27359(8) 0.0194(3) Uani 1 1 d D . . H12 H 1.0478 0.2470 0.2461 0.023 Uiso 1 1 calc R . . C13 C 1.2021(2) 0.24590(11) 0.32602(8) 0.0219(4) Uani 1 1 d D . . H13 H 1.1865 0.1844 0.3348 0.026 Uiso 1 1 calc R . . C14 C 1.3092(2) 0.29740(12) 0.36561(8) 0.0234(4) Uani 1 1 d D . . H14 H 1.3691 0.2714 0.4010 0.028 Uiso 1 1 calc R . . C15 C 1.3274(2) 0.38725(12) 0.35266(8) 0.0235(4) Uani 1 1 d D . . H15 H 1.4012 0.4230 0.3793 0.028 Uiso 1 1 calc R . . C16 C 1.2390(2) 0.42561(11) 0.30131(8) 0.0190(3) Uani 1 1 d D . . H16 H 1.2509 0.4877 0.2938 0.023 Uiso 1 1 calc R . . C17 C 1.1167(2) 0.50854(11) 0.18952(8) 0.0200(3) Uani 1 1 d . . . H17A H 1.2416 0.5034 0.1896 0.024 Uiso 1 1 calc R . . H17B H 1.0873 0.5499 0.2224 0.024 Uiso 1 1 calc R . . H17C H 1.0705 0.5311 0.1490 0.024 Uiso 1 1 calc R . . C21 C 0.80896(18) 0.45152(10) 0.27335(7) 0.0134(3) Uani 1 1 d D . . C22 C 0.81918(19) 0.54152(10) 0.29011(7) 0.0144(3) Uani 1 1 d D . . H22 H 0.8282 0.5849 0.2583 0.017 Uiso 1 1 calc R . . C23 C 0.81669(19) 0.56998(10) 0.35121(7) 0.0156(3) Uani 1 1 d D . . H23 H 0.8227 0.6320 0.3603 0.019 Uiso 1 1 calc R . . C24 C 0.8054(2) 0.50848(11) 0.39996(7) 0.0165(3) Uani 1 1 d D . . C25 C 0.7928(2) 0.41798(11) 0.38333(7) 0.0176(3) Uani 1 1 d D . . H25 H 0.7821 0.3744 0.4149 0.021 Uiso 1 1 calc R . . C26 C 0.79567(19) 0.39095(10) 0.32206(7) 0.0148(3) Uani 1 1 d D . . H26 H 0.7884 0.3290 0.3128 0.018 Uiso 1 1 calc R . . C27 C 0.7695(3) 0.47153(12) 0.50895(8) 0.0275(4) Uani 1 1 d . . . H27A H 0.6486 0.4543 0.5029 0.033 Uiso 1 1 calc R . . H27B H 0.7913 0.4984 0.5503 0.033 Uiso 1 1 calc R . . H27C H 0.8418 0.4185 0.5057 0.033 Uiso 1 1 calc R . . C28 C 0.7828(3) 0.62892(12) 0.47634(8) 0.0280(4) Uani 1 1 d . . . H28A H 0.8579 0.6661 0.4526 0.034 Uiso 1 1 calc R . . H28B H 0.8096 0.6386 0.5210 0.034 Uiso 1 1 calc R . . H28C H 0.6630 0.6450 0.4654 0.034 Uiso 1 1 calc R . . C31 C 0.74590(19) 0.48334(10) 0.15687(7) 0.0134(3) Uani 1 1 d D . . C32 C 0.5944(2) 0.52746(10) 0.16860(7) 0.0149(3) Uani 1 1 d D . . H32 H 0.5512 0.5217 0.2086 0.018 Uiso 1 1 calc R . . C33 C 0.5044(2) 0.57945(10) 0.12413(7) 0.0155(3) Uani 1 1 d D . . H33 H 0.4011 0.6077 0.1342 0.019 Uiso 1 1 calc R . . C34 C 0.5631(2) 0.59119(10) 0.06447(7) 0.0155(3) Uani 1 1 d D . . C35 C 0.7112(2) 0.54408(11) 0.05148(7) 0.0176(3) Uani 1 1 d D . . H35 H 0.7530 0.5484 0.0112 0.021 Uiso 1 1 calc R . . C36 C 0.7978(2) 0.49140(11) 0.09623(7) 0.0168(3) Uani 1 1 d D . . H36 H 0.8964 0.4595 0.0853 0.020 Uiso 1 1 calc R . . C37 C 0.5425(2) 0.65474(11) -0.04060(7) 0.0212(4) Uani 1 1 d . . . H37A H 0.6627 0.6737 -0.0371 0.025 Uiso 1 1 calc R . . H37B H 0.4736 0.6988 -0.0649 0.025 Uiso 1 1 calc R . . H37C H 0.5331 0.5966 -0.0614 0.025 Uiso 1 1 calc R . . C38 C 0.3073(2) 0.67740(12) 0.03038(8) 0.0258(4) Uani 1 1 d . . . H38A H 0.2333 0.6255 0.0354 0.031 Uiso 1 1 calc R . . H38B H 0.2634 0.7123 -0.0058 0.031 Uiso 1 1 calc R . . H38C H 0.3086 0.7147 0.0678 0.031 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 0.0202(7) 0.0202(7) 0.0154(7) -0.0005(5) 0.0007(5) 0.0055(6) N2 0.0410(9) 0.0182(7) 0.0131(7) 0.0009(5) 0.0029(6) 0.0025(6) N3 0.0236(7) 0.0196(7) 0.0159(7) 0.0036(5) -0.0021(6) 0.0040(6) C1 0.0170(7) 0.0135(7) 0.0116(7) 0.0013(6) -0.0021(6) 0.0010(6) C2 0.0191(8) 0.0153(7) 0.0159(8) 0.0005(6) -0.0005(6) 0.0011(6) C3 0.0189(8) 0.0178(8) 0.0223(8) 0.0030(6) -0.0015(6) -0.0035(6) C4 0.0255(9) 0.0136(7) 0.0221(8) -0.0009(6) -0.0074(7) -0.0009(6) C5 0.0246(9) 0.0167(8) 0.0165(8) -0.0040(6) -0.0047(6) 0.0060(6) C6 0.0182(8) 0.0166(8) 0.0132(7) 0.0006(6) -0.0028(6) 0.0028(6) C7 0.0150(7) 0.0218(8) 0.0146(7) 0.0027(6) 0.0022(6) 0.0045(6) C8 0.0141(7) 0.0158(7) 0.0153(7) 0.0005(6) 0.0006(6) 0.0007(6) C9 0.0128(7) 0.0127(7) 0.0133(7) 0.0000(6) 0.0003(6) 0.0003(6) C11 0.0126(7) 0.0187(8) 0.0150(7) 0.0000(6) 0.0023(6) 0.0036(6) C12 0.0195(8) 0.0190(8) 0.0191(8) -0.0033(6) -0.0030(6) 0.0035(6) C13 0.0277(9) 0.0184(8) 0.0192(8) -0.0004(6) -0.0004(7) 0.0075(7) C14 0.0252(9) 0.0277(9) 0.0165(8) -0.0025(7) -0.0042(7) 0.0120(7) C15 0.0202(8) 0.0292(9) 0.0203(9) -0.0079(7) -0.0030(7) 0.0030(7) C16 0.0170(8) 0.0189(8) 0.0212(8) -0.0025(6) 0.0018(6) 0.0011(6) C17 0.0160(8) 0.0202(8) 0.0240(9) 0.0039(7) 0.0021(6) -0.0018(6) C21 0.0109(7) 0.0152(7) 0.0140(7) 0.0001(6) 0.0003(6) -0.0003(6) C22 0.0134(7) 0.0146(7) 0.0151(7) 0.0031(6) -0.0001(6) -0.0005(6) C23 0.0166(8) 0.0118(7) 0.0179(8) -0.0010(6) -0.0008(6) 0.0003(6) C24 0.0170(8) 0.0180(8) 0.0142(7) -0.0003(6) -0.0004(6) 0.0025(6) C25 0.0203(8) 0.0172(8) 0.0151(8) 0.0040(6) 0.0012(6) 0.0007(6) C26 0.0150(7) 0.0119(7) 0.0171(8) 0.0002(6) -0.0003(6) 0.0006(6) C27 0.0419(11) 0.0261(9) 0.0147(8) 0.0018(7) 0.0045(7) 0.0045(8) C28 0.0441(11) 0.0224(9) 0.0176(8) -0.0048(7) 0.0041(8) 0.0004(8) C31 0.0148(7) 0.0111(7) 0.0139(7) -0.0002(5) -0.0017(6) -0.0007(6) C32 0.0156(7) 0.0152(7) 0.0139(7) -0.0005(6) 0.0010(6) -0.0037(6) C33 0.0133(7) 0.0146(7) 0.0183(8) -0.0007(6) -0.0004(6) -0.0002(6) C34 0.0182(8) 0.0115(7) 0.0161(8) -0.0003(6) -0.0042(6) -0.0029(6) C35 0.0225(8) 0.0175(8) 0.0128(7) 0.0009(6) 0.0015(6) -0.0013(6) C36 0.0163(8) 0.0172(8) 0.0170(8) -0.0003(6) 0.0022(6) 0.0011(6) C37 0.0286(9) 0.0178(8) 0.0166(8) 0.0030(6) -0.0032(7) 0.0002(7) C38 0.0270(9) 0.0257(9) 0.0238(9) 0.0034(7) -0.0043(7) 0.0088(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 C7 1.275(2) . ? N1 C6 1.425(2) . ? N2 C24 1.386(2) . ? N2 C28 1.451(2) . ? N2 C27 1.451(2) . ? N3 C34 1.384(2) . ? N3 C37 1.451(2) . ? N3 C38 1.452(2) . ? C1 C2 1.394(2) . ? C1 C6 1.401(2) . ? C1 C9 1.538(2) . ? C2 C3 1.390(2) . ? C3 C4 1.389(2) . ? C4 C5 1.384(2) . ? C5 C6 1.397(2) . ? C7 C8 1.516(2) . ? C8 C17 1.538(2) . ? C8 C11 1.553(2) . ? C8 C9 1.598(2) . ? C9 C21 1.539(2) . ? C9 C31 1.554(2) . ? C11 C12 1.395(2) . ? C11 C16 1.397(2) . ? C12 C13 1.388(2) . ? C13 C14 1.387(2) . ? C14 C15 1.384(3) . ? C15 C16 1.387(2) . ? C21 C26 1.396(2) . ? C21 C22 1.397(2) . ? C22 C23 1.384(2) . ? C23 C24 1.404(2) . ? C24 C25 1.404(2) . ? C25 C26 1.381(2) . ? C31 C32 1.395(2) . ? C31 C36 1.399(2) . ? C32 C33 1.387(2) . ? C33 C34 1.405(2) . ? C34 C35 1.401(2) . ? C35 C36 1.385(2) . ? 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 C7 N1 C6 117.27(14) . . ? C24 N2 C28 119.93(14) . . ? C24 N2 C27 119.11(14) . . ? C28 N2 C27 116.29(14) . . ? C34 N3 C37 119.47(14) . . ? C34 N3 C38 119.46(14) . . ? C37 N3 C38 118.57(13) . . ? C2 C1 C6 118.03(14) . . ? C2 C1 C9 121.56(14) . . ? C6 C1 C9 120.19(14) . . ? C3 C2 C1 121.36(15) . . ? C4 C3 C2 120.07(16) . . ? C5 C4 C3 119.39(15) . . ? C4 C5 C6 120.61(15) . . ? C5 C6 C1 120.44(15) . . ? C5 C6 N1 116.18(14) . . ? C1 C6 N1 123.38(14) . . ? N1 C7 C8 127.90(15) . . ? C7 C8 C17 107.96(13) . . ? C7 C8 C11 104.48(12) . . ? C17 C8 C11 109.35(13) . . ? C7 C8 C9 110.71(12) . . ? C17 C8 C9 112.07(12) . . ? C11 C8 C9 111.93(12) . . ? C1 C9 C21 112.60(12) . . ? C1 C9 C31 103.53(11) . . ? C21 C9 C31 112.15(12) . . ? C1 C9 C8 109.49(12) . . ? C21 C9 C8 106.46(12) . . ? C31 C9 C8 112.72(12) . . ? C12 C11 C16 117.58(14) . . ? C12 C11 C8 121.17(14) . . ? C16 C11 C8 121.23(14) . . ? C13 C12 C11 121.30(15) . . ? C14 C13 C12 120.38(16) . . ? C15 C14 C13 118.92(16) . . ? C14 C15 C16 120.74(16) . . ? C15 C16 C11 121.05(16) . . ? C26 C21 C22 116.07(14) . . ? C26 C21 C9 122.10(13) . . ? C22 C21 C9 121.28(13) . . ? C23 C22 C21 122.58(14) . . ? C22 C23 C24 120.93(14) . . ? N2 C24 C23 121.60(14) . . ? N2 C24 C25 121.64(14) . . ? C23 C24 C25 116.76(14) . . ? C26 C25 C24 121.41(14) . . ? C25 C26 C21 122.25(14) . . ? C32 C31 C36 115.70(14) . . ? C32 C31 C9 120.87(13) . . ? C36 C31 C9 123.06(13) . . ? C33 C32 C31 122.52(14) . . ? C32 C33 C34 121.24(14) . . ? N3 C34 C35 121.77(14) . . ? N3 C34 C33 121.68(14) . . ? C35 C34 C33 116.55(14) . . ? C36 C35 C34 121.28(15) . . ? C35 C36 C31 122.55(15) . . ? 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 C6 C1 C2 C3 3.3(2) . . . . ? C9 C1 C2 C3 177.79(14) . . . . ? C1 C2 C3 C4 -0.8(2) . . . . ? C2 C3 C4 C5 -1.5(2) . . . . ? C3 C4 C5 C6 1.2(2) . . . . ? C4 C5 C6 C1 1.3(2) . . . . ? C4 C5 C6 N1 -178.86(14) . . . . ? C2 C1 C6 C5 -3.5(2) . . . . ? C9 C1 C6 C5 -178.12(14) . . . . ? C2 C1 C6 N1 176.69(14) . . . . ? C9 C1 C6 N1 2.1(2) . . . . ? C7 N1 C6 C5 -166.95(14) . . . . ? C7 N1 C6 C1 12.9(2) . . . . ? C6 N1 C7 C8 1.6(2) . . . . ? N1 C7 C8 C17 -150.17(16) . . . . ? N1 C7 C8 C11 93.51(18) . . . . ? N1 C7 C8 C9 -27.2(2) . . . . ? C2 C1 C9 C21 40.50(19) . . . . ? C6 C1 C9 C21 -145.09(14) . . . . ? C2 C1 C9 C31 -80.85(17) . . . . ? C6 C1 C9 C31 93.57(16) . . . . ? C2 C1 C9 C8 158.72(14) . . . . ? C6 C1 C9 C8 -26.87(18) . . . . ? C7 C8 C9 C1 36.17(16) . . . . ? C17 C8 C9 C1 156.77(13) . . . . ? C11 C8 C9 C1 -79.95(15) . . . . ? C7 C8 C9 C21 158.15(12) . . . . ? C17 C8 C9 C21 -81.25(15) . . . . ? C11 C8 C9 C21 42.03(16) . . . . ? C7 C8 C9 C31 -78.49(15) . . . . ? C17 C8 C9 C31 42.11(17) . . . . ? C11 C8 C9 C31 165.39(12) . . . . ? C7 C8 C11 C12 -49.29(18) . . . . ? C17 C8 C11 C12 -164.65(14) . . . . ? C9 C8 C11 C12 70.55(18) . . . . ? C7 C8 C11 C16 128.93(15) . . . . ? C17 C8 C11 C16 13.6(2) . . . . ? C9 C8 C11 C16 -111.23(16) . . . . ? C16 C11 C12 C13 1.2(2) . . . . ? C8 C11 C12 C13 179.45(15) . . . . ? C11 C12 C13 C14 -2.2(3) . . . . ? C12 C13 C14 C15 1.3(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C11 -1.6(3) . . . . ? C12 C11 C16 C15 0.8(2) . . . . ? C8 C11 C16 C15 -177.52(14) . . . . ? C1 C9 C21 C26 30.04(19) . . . . ? C31 C9 C21 C26 146.33(14) . . . . ? C8 C9 C21 C26 -89.95(16) . . . . ? C1 C9 C21 C22 -158.84(13) . . . . ? C31 C9 C21 C22 -42.54(19) . . . . ? C8 C9 C21 C22 81.18(16) . . . . ? C26 C21 C22 C23 0.1(2) . . . . ? C9 C21 C22 C23 -171.54(14) . . . . ? C21 C22 C23 C24 0.7(2) . . . . ? C28 N2 C24 C23 15.3(3) . . . . ? C27 N2 C24 C23 170.13(16) . . . . ? C28 N2 C24 C25 -165.86(16) . . . . ? C27 N2 C24 C25 -11.0(2) . . . . ? C22 C23 C24 N2 177.50(15) . . . . ? C22 C23 C24 C25 -1.4(2) . . . . ? N2 C24 C25 C26 -177.42(15) . . . . ? C23 C24 C25 C26 1.5(2) . . . . ? C24 C25 C26 C21 -0.8(2) . . . . ? C22 C21 C26 C25 0.0(2) . . . . ? C9 C21 C26 C25 171.54(14) . . . . ? C1 C9 C31 C32 90.53(16) . . . . ? C21 C9 C31 C32 -31.12(19) . . . . ? C8 C9 C31 C32 -151.26(13) . . . . ? C1 C9 C31 C36 -82.27(17) . . . . ? C21 C9 C31 C36 156.08(14) . . . . ? C8 C9 C31 C36 35.94(19) . . . . ? C36 C31 C32 C33 -2.8(2) . . . . ? C9 C31 C32 C33 -176.13(14) . . . . ? C31 C32 C33 C34 -0.7(2) . . . . ? C37 N3 C34 C35 3.2(2) . . . . ? C38 N3 C34 C35 165.04(15) . . . . ? C37 N3 C34 C33 -177.79(14) . . . . ? C38 N3 C34 C33 -16.0(2) . . . . ? C32 C33 C34 N3 -175.80(14) . . . . ? C32 C33 C34 C35 3.3(2) . . . . ? N3 C34 C35 C36 176.78(15) . . . . ? C33 C34 C35 C36 -2.3(2) . . . . ? C34 C35 C36 C31 -1.3(2) . . . . ? C32 C31 C36 C35 3.8(2) . . . . ? C9 C31 C36 C35 176.98(14) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.379 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.050 #===END data_vidal1s_compound_13k _database_code_depnum_ccdc_archive 'CCDC 779906' #TrackingRef '- Alajarin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H27 N O2' _chemical_formula_weight 433.53 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 9.5349(14) _cell_length_b 10.3815(15) _cell_length_c 13.640(2) _cell_angle_alpha 68.248(2) _cell_angle_beta 71.532(2) _cell_angle_gamma 65.462(2) _cell_volume 1119.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3514 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.46 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9834 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_process_details SADABS _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 SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12934 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.11 _reflns_number_total 5013 _reflns_number_gt 4235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0512P)^2^+0.3937P] 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 'Me rigid, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5013 _refine_ls_number_parameters 301 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 -0.01885(15) 0.07488(14) 0.84942(11) 0.0167(3) Uani 1 1 d . . . O1 O -0.14943(14) 0.95537(11) 0.56149(9) 0.0227(3) Uani 1 1 d . . . O2 O 0.50783(13) 0.16492(12) 1.05811(9) 0.0191(3) Uani 1 1 d . . . C1 C 0.13157(17) 0.24351(16) 0.73570(12) 0.0139(3) Uani 1 1 d . . . C2 C 0.25840(18) 0.26293(17) 0.65330(12) 0.0172(3) Uani 1 1 d . . . H2 H 0.2847 0.3486 0.6361 0.021 Uiso 1 1 calc R . . C3 C 0.34706(19) 0.16011(17) 0.59589(13) 0.0204(3) Uani 1 1 d . . . H3 H 0.4330 0.1760 0.5401 0.024 Uiso 1 1 calc R . . C4 C 0.31113(19) 0.03414(17) 0.61943(13) 0.0204(3) Uani 1 1 d . . . H4 H 0.3699 -0.0351 0.5788 0.024 Uiso 1 1 calc R . . C5 C 0.18827(18) 0.01076(16) 0.70306(13) 0.0175(3) Uani 1 1 d . . . H5 H 0.1643 -0.0763 0.7207 0.021 Uiso 1 1 calc R . . C6 C 0.09921(17) 0.11335(16) 0.76182(12) 0.0144(3) Uani 1 1 d . . . C7 C -0.11464(18) 0.17308(16) 0.89613(12) 0.0159(3) Uani 1 1 d . . . H7 H -0.1894 0.1433 0.9563 0.019 Uiso 1 1 calc R . . C8 C -0.12418(17) 0.33225(16) 0.86748(12) 0.0140(3) Uani 1 1 d . . . C9 C 0.04296(17) 0.35107(15) 0.80579(12) 0.0128(3) Uani 1 1 d . . . C10 C -0.18571(19) 0.37831(18) 0.97248(13) 0.0190(3) Uani 1 1 d . . . H10A H -0.2946 0.3806 1.0009 0.023 Uiso 1 1 calc R . . H10B H -0.1813 0.4765 0.9581 0.023 Uiso 1 1 calc R . . H10C H -0.1204 0.3072 1.0253 0.023 Uiso 1 1 calc R . . C11 C -0.24747(17) 0.42192(16) 0.79379(12) 0.0153(3) Uani 1 1 d D . . C12 C -0.25350(19) 0.36910(17) 0.71539(13) 0.0195(3) Uani 1 1 d D . . H12 H -0.1797 0.2767 0.7063 0.023 Uiso 1 1 calc R . . C13 C -0.3650(2) 0.44881(19) 0.65043(14) 0.0239(4) Uani 1 1 d D . . H13 H -0.3662 0.4113 0.5970 0.029 Uiso 1 1 calc R . . C14 C -0.4747(2) 0.58281(19) 0.66318(14) 0.0251(4) Uani 1 1 d D . . H14 H -0.5521 0.6369 0.6195 0.030 Uiso 1 1 calc R . . C15 C -0.4702(2) 0.63684(18) 0.74004(15) 0.0246(4) Uani 1 1 d D . . H15 H -0.5446 0.7291 0.7489 0.029 Uiso 1 1 calc R . . C16 C -0.35830(18) 0.55782(17) 0.80458(14) 0.0200(3) Uani 1 1 d D . . H16 H -0.3570 0.5969 0.8571 0.024 Uiso 1 1 calc R . . C21 C 0.00978(17) 0.51323(16) 0.73796(12) 0.0136(3) Uani 1 1 d D . . C22 C -0.01216(17) 0.55733(16) 0.63204(12) 0.0153(3) Uani 1 1 d D . . H22 H 0.0083 0.4843 0.5984 0.018 Uiso 1 1 calc R . . C23 C -0.06288(18) 0.70462(17) 0.57509(13) 0.0177(3) Uani 1 1 d D . . H23 H -0.0766 0.7315 0.5033 0.021 Uiso 1 1 calc R . . C24 C -0.09369(18) 0.81307(16) 0.62317(13) 0.0169(3) Uani 1 1 d D . . C25 C -0.06847(18) 0.77304(16) 0.72637(12) 0.0160(3) Uani 1 1 d D . . H25 H -0.0849 0.8464 0.7586 0.019 Uiso 1 1 calc R . . C26 C -0.01869(17) 0.62411(16) 0.78309(12) 0.0152(3) Uani 1 1 d D . . H26 H -0.0038 0.5977 0.8545 0.018 Uiso 1 1 calc R . . C27 C -0.1763(2) 1.07055(17) 0.60532(14) 0.0231(4) Uani 1 1 d . . . H27A H -0.2590 1.0674 0.6700 0.028 Uiso 1 1 calc R . . H27B H -0.2092 1.1659 0.5520 0.028 Uiso 1 1 calc R . . H27C H -0.0792 1.0575 0.6241 0.028 Uiso 1 1 calc R . . C31 C 0.15722(17) 0.30512(16) 0.88132(12) 0.0138(3) Uani 1 1 d D . . C32 C 0.27284(17) 0.37010(16) 0.85154(12) 0.0156(3) Uani 1 1 d D . . H32 H 0.2726 0.4501 0.7883 0.019 Uiso 1 1 calc R . . C33 C 0.38706(18) 0.32125(16) 0.91134(13) 0.0167(3) Uani 1 1 d D . . H33 H 0.4631 0.3684 0.8892 0.020 Uiso 1 1 calc R . . C34 C 0.39154(17) 0.20351(16) 1.00373(12) 0.0150(3) Uani 1 1 d D . . C35 C 0.28111(18) 0.13406(16) 1.03387(12) 0.0156(3) Uani 1 1 d D . . H35 H 0.2836 0.0524 1.0961 0.019 Uiso 1 1 calc R . . C36 C 0.16703(17) 0.18443(16) 0.97264(12) 0.0148(3) Uani 1 1 d D . . H36 H 0.0933 0.1351 0.9937 0.018 Uiso 1 1 calc R . . C37 C 0.50730(19) 0.05325(18) 1.15855(13) 0.0203(3) Uani 1 1 d . . . H37A H 0.4113 0.0879 1.2096 0.024 Uiso 1 1 calc R . . H37B H 0.5992 0.0317 1.1872 0.024 Uiso 1 1 calc R . . H37C H 0.5110 -0.0364 1.1477 0.024 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 0.0157(6) 0.0128(6) 0.0209(7) -0.0023(5) -0.0049(5) -0.0051(5) O1 0.0335(7) 0.0103(5) 0.0243(6) -0.0009(5) -0.0122(5) -0.0060(5) O2 0.0184(6) 0.0204(6) 0.0200(6) -0.0029(5) -0.0078(5) -0.0073(5) C1 0.0139(7) 0.0108(7) 0.0150(7) -0.0020(6) -0.0059(6) -0.0015(6) C2 0.0183(8) 0.0135(7) 0.0175(8) -0.0025(6) -0.0027(6) -0.0052(6) C3 0.0191(8) 0.0196(8) 0.0152(8) -0.0040(6) 0.0002(6) -0.0031(6) C4 0.0226(8) 0.0168(8) 0.0182(8) -0.0083(6) -0.0065(7) 0.0014(6) C5 0.0198(8) 0.0112(7) 0.0223(8) -0.0046(6) -0.0096(6) -0.0020(6) C6 0.0143(7) 0.0128(7) 0.0159(7) -0.0023(6) -0.0067(6) -0.0030(6) C7 0.0159(7) 0.0144(7) 0.0174(8) -0.0003(6) -0.0038(6) -0.0083(6) C8 0.0144(7) 0.0125(7) 0.0146(7) -0.0030(6) -0.0023(6) -0.0052(6) C9 0.0136(7) 0.0101(7) 0.0144(7) -0.0020(6) -0.0022(6) -0.0052(6) C10 0.0171(8) 0.0198(8) 0.0194(8) -0.0076(6) -0.0001(6) -0.0061(6) C11 0.0135(7) 0.0138(7) 0.0170(7) -0.0012(6) -0.0009(6) -0.0073(6) C12 0.0188(8) 0.0164(8) 0.0231(8) -0.0061(6) -0.0043(6) -0.0051(6) C13 0.0257(9) 0.0250(9) 0.0240(9) -0.0047(7) -0.0078(7) -0.0110(7) C14 0.0190(8) 0.0227(8) 0.0287(9) 0.0038(7) -0.0109(7) -0.0075(7) C15 0.0190(8) 0.0144(8) 0.0339(10) -0.0016(7) -0.0053(7) -0.0040(6) C16 0.0181(8) 0.0143(7) 0.0267(9) -0.0045(7) -0.0025(7) -0.0069(6) C21 0.0114(7) 0.0123(7) 0.0162(7) -0.0030(6) -0.0016(6) -0.0049(6) C22 0.0164(7) 0.0139(7) 0.0171(8) -0.0057(6) -0.0021(6) -0.0062(6) C23 0.0215(8) 0.0169(7) 0.0151(7) -0.0014(6) -0.0061(6) -0.0077(6) C24 0.0162(7) 0.0126(7) 0.0194(8) -0.0008(6) -0.0040(6) -0.0051(6) C25 0.0167(7) 0.0130(7) 0.0191(8) -0.0062(6) -0.0020(6) -0.0053(6) C26 0.0152(7) 0.0160(7) 0.0148(7) -0.0038(6) -0.0022(6) -0.0065(6) C27 0.0284(9) 0.0120(7) 0.0272(9) -0.0042(7) -0.0054(7) -0.0063(7) C31 0.0134(7) 0.0130(7) 0.0143(7) -0.0058(6) -0.0014(6) -0.0029(6) C32 0.0161(7) 0.0125(7) 0.0166(7) -0.0030(6) -0.0021(6) -0.0049(6) C33 0.0157(7) 0.0151(7) 0.0212(8) -0.0055(6) -0.0018(6) -0.0077(6) C34 0.0139(7) 0.0140(7) 0.0178(8) -0.0080(6) -0.0033(6) -0.0020(6) C35 0.0178(8) 0.0137(7) 0.0134(7) -0.0027(6) -0.0020(6) -0.0052(6) C36 0.0149(7) 0.0137(7) 0.0170(7) -0.0057(6) -0.0012(6) -0.0061(6) C37 0.0194(8) 0.0223(8) 0.0180(8) -0.0051(7) -0.0067(6) -0.0039(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 C7 1.272(2) . ? N1 C6 1.422(2) . ? O1 C24 1.3721(18) . ? O1 C27 1.4253(19) . ? O2 C34 1.3682(18) . ? O2 C37 1.4297(19) . ? C1 C2 1.393(2) . ? C1 C6 1.403(2) . ? C1 C9 1.540(2) . ? C2 C3 1.385(2) . ? C3 C4 1.386(2) . ? C4 C5 1.384(2) . ? C5 C6 1.396(2) . ? C7 C8 1.520(2) . ? C8 C10 1.538(2) . ? C8 C11 1.551(2) . ? C8 C9 1.604(2) . ? C9 C21 1.5423(19) . ? C9 C31 1.546(2) . ? C11 C16 1.395(2) . ? C11 C12 1.395(2) . ? C12 C13 1.387(2) . ? C13 C14 1.384(2) . ? C14 C15 1.378(3) . ? C15 C16 1.386(2) . ? C21 C26 1.392(2) . ? C21 C22 1.401(2) . ? C22 C23 1.385(2) . ? C23 C24 1.391(2) . ? C24 C25 1.382(2) . ? C25 C26 1.397(2) . ? C31 C36 1.396(2) . ? C31 C32 1.402(2) . ? C32 C33 1.381(2) . ? C33 C34 1.390(2) . ? C34 C35 1.391(2) . ? C35 C36 1.391(2) . ? 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 C7 N1 C6 117.71(13) . . ? C24 O1 C27 117.42(13) . . ? C34 O2 C37 117.40(12) . . ? C2 C1 C6 117.92(14) . . ? C2 C1 C9 121.10(13) . . ? C6 C1 C9 120.51(13) . . ? C3 C2 C1 121.47(14) . . ? C2 C3 C4 120.38(15) . . ? C5 C4 C3 119.02(14) . . ? C4 C5 C6 120.89(14) . . ? C5 C6 C1 120.25(14) . . ? C5 C6 N1 116.23(13) . . ? C1 C6 N1 123.49(13) . . ? N1 C7 C8 128.00(14) . . ? C7 C8 C10 107.48(12) . . ? C7 C8 C11 105.25(12) . . ? C10 C8 C11 109.48(12) . . ? C7 C8 C9 111.07(12) . . ? C10 C8 C9 112.49(12) . . ? C11 C8 C9 110.77(12) . . ? C1 C9 C21 112.02(12) . . ? C1 C9 C31 102.52(11) . . ? C21 C9 C31 111.99(12) . . ? C1 C9 C8 109.72(11) . . ? C21 C9 C8 106.85(11) . . ? C31 C9 C8 113.82(12) . . ? C16 C11 C12 117.44(14) . . ? C16 C11 C8 121.09(14) . . ? C12 C11 C8 121.46(13) . . ? C13 C12 C11 121.31(15) . . ? C14 C13 C12 120.25(16) . . ? C15 C14 C13 119.22(16) . . ? C14 C15 C16 120.63(16) . . ? C15 C16 C11 121.14(16) . . ? C26 C21 C22 117.01(13) . . ? C26 C21 C9 121.46(13) . . ? C22 C21 C9 121.07(13) . . ? C23 C22 C21 121.75(14) . . ? C22 C23 C24 119.92(14) . . ? O1 C24 C25 125.00(14) . . ? O1 C24 C23 115.27(14) . . ? C25 C24 C23 119.72(14) . . ? C24 C25 C26 119.63(14) . . ? C21 C26 C25 121.91(14) . . ? C36 C31 C32 116.45(14) . . ? C36 C31 C9 122.48(13) . . ? C32 C31 C9 120.38(13) . . ? C33 C32 C31 121.97(14) . . ? C32 C33 C34 120.42(14) . . ? O2 C34 C33 115.92(13) . . ? O2 C34 C35 125.05(14) . . ? C33 C34 C35 119.03(14) . . ? C36 C35 C34 119.82(14) . . ? C35 C36 C31 122.24(14) . . ? 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 C6 C1 C2 C3 2.3(2) . . . . ? C9 C1 C2 C3 174.43(14) . . . . ? C1 C2 C3 C4 0.0(2) . . . . ? C2 C3 C4 C5 -1.8(2) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? C4 C5 C6 C1 1.0(2) . . . . ? C4 C5 C6 N1 -176.89(14) . . . . ? C2 C1 C6 C5 -2.8(2) . . . . ? C9 C1 C6 C5 -174.96(13) . . . . ? C2 C1 C6 N1 174.98(14) . . . . ? C9 C1 C6 N1 2.8(2) . . . . ? C7 N1 C6 C5 -171.44(14) . . . . ? C7 N1 C6 C1 10.7(2) . . . . ? C6 N1 C7 C8 2.6(2) . . . . ? N1 C7 C8 C10 -149.34(16) . . . . ? N1 C7 C8 C11 94.03(18) . . . . ? N1 C7 C8 C9 -25.9(2) . . . . ? C2 C1 C9 C21 44.33(18) . . . . ? C6 C1 C9 C21 -143.70(13) . . . . ? C2 C1 C9 C31 -75.90(16) . . . . ? C6 C1 C9 C31 96.06(15) . . . . ? C2 C1 C9 C8 162.83(13) . . . . ? C6 C1 C9 C8 -25.21(18) . . . . ? C7 C8 C9 C1 33.67(16) . . . . ? C10 C8 C9 C1 154.19(12) . . . . ? C11 C8 C9 C1 -82.92(14) . . . . ? C7 C8 C9 C21 155.32(12) . . . . ? C10 C8 C9 C21 -84.16(15) . . . . ? C11 C8 C9 C21 38.73(15) . . . . ? C7 C8 C9 C31 -80.53(15) . . . . ? C10 C8 C9 C31 39.99(16) . . . . ? C11 C8 C9 C31 162.88(12) . . . . ? C7 C8 C11 C16 138.68(14) . . . . ? C10 C8 C11 C16 23.43(19) . . . . ? C9 C8 C11 C16 -101.19(16) . . . . ? C7 C8 C11 C12 -40.35(18) . . . . ? C10 C8 C11 C12 -155.61(14) . . . . ? C9 C8 C11 C12 79.78(16) . . . . ? C16 C11 C12 C13 0.2(2) . . . . ? C8 C11 C12 C13 179.27(14) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C12 C13 C14 C15 0.9(2) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C12 C11 C16 C15 0.2(2) . . . . ? C8 C11 C16 C15 -178.87(14) . . . . ? C1 C9 C21 C26 -157.85(13) . . . . ? C31 C9 C21 C26 -43.30(18) . . . . ? C8 C9 C21 C26 81.97(16) . . . . ? C1 C9 C21 C22 30.16(19) . . . . ? C31 C9 C21 C22 144.71(14) . . . . ? C8 C9 C21 C22 -90.02(16) . . . . ? C26 C21 C22 C23 -1.2(2) . . . . ? C9 C21 C22 C23 171.09(14) . . . . ? C21 C22 C23 C24 -0.1(2) . . . . ? C27 O1 C24 C25 3.1(2) . . . . ? C27 O1 C24 C23 -177.32(14) . . . . ? C22 C23 C24 O1 -177.43(14) . . . . ? C22 C23 C24 C25 2.1(2) . . . . ? O1 C24 C25 C26 176.81(14) . . . . ? C23 C24 C25 C26 -2.7(2) . . . . ? C22 C21 C26 C25 0.6(2) . . . . ? C9 C21 C26 C25 -171.66(13) . . . . ? C24 C25 C26 C21 1.3(2) . . . . ? C1 C9 C31 C36 -80.65(16) . . . . ? C21 C9 C31 C36 159.10(13) . . . . ? C8 C9 C31 C36 37.77(19) . . . . ? C1 C9 C31 C32 89.53(15) . . . . ? C21 C9 C31 C32 -30.73(18) . . . . ? C8 C9 C31 C32 -152.06(13) . . . . ? C36 C31 C32 C33 -2.3(2) . . . . ? C9 C31 C32 C33 -173.09(13) . . . . ? C31 C32 C33 C34 0.6(2) . . . . ? C37 O2 C34 C33 174.48(13) . . . . ? C37 O2 C34 C35 -5.8(2) . . . . ? C32 C33 C34 O2 -179.10(13) . . . . ? C32 C33 C34 C35 1.2(2) . . . . ? O2 C34 C35 C36 179.25(13) . . . . ? C33 C34 C35 C36 -1.0(2) . . . . ? C34 C35 C36 C31 -0.9(2) . . . . ? C32 C31 C36 C35 2.5(2) . . . . ? C9 C31 C36 C35 173.02(13) . . . . ? 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 C36 H36 N1 0.95 2.59 3.358(2) 138.4 2_557 _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.391 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.048 #===END data_ivbbf81s_compound_18a _database_code_depnum_ccdc_archive 'CCDC 779907' #TrackingRef '- Alajarin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H25 N' _chemical_formula_weight 435.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.9420(4) _cell_length_b 19.4575(7) _cell_length_c 23.8119(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4606.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8839 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.92 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9787 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details SADABS _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 SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50447 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.22 _reflns_number_total 5486 _reflns_number_gt 4980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0615P)^2^+2.5360P] 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 Riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5486 _refine_ls_number_parameters 307 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.045 _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 0.56378(11) 0.07864(5) 0.43541(4) 0.0191(2) Uani 1 1 d . . . C1 C 0.59283(13) 0.02624(6) 0.34326(5) 0.0200(3) Uani 1 1 d . . . C2 C 0.66832(15) -0.01529(7) 0.30760(6) 0.0257(3) Uani 1 1 d D . . H2 H 0.6331 -0.0268 0.2717 0.031 Uiso 1 1 calc R . . C3 C 0.79380(15) -0.04037(7) 0.32305(6) 0.0294(3) Uani 1 1 d D . . H3 H 0.8441 -0.0684 0.2980 0.035 Uiso 1 1 calc R . . C4 C 0.84432(15) -0.02381(7) 0.37555(7) 0.0290(3) Uani 1 1 d D . . H4 H 0.9308 -0.0399 0.3863 0.035 Uiso 1 1 calc R . . C5 C 0.77002(14) 0.01591(7) 0.41262(6) 0.0249(3) Uani 1 1 d D . . H5 H 0.8057 0.0266 0.4486 0.030 Uiso 1 1 calc R . . C6 C 0.64247(13) 0.04038(6) 0.39730(5) 0.0196(3) Uani 1 1 d D . . C7 C 0.42449(13) 0.08611(6) 0.42545(5) 0.0177(2) Uani 1 1 d D . . C8 C 0.33733(13) 0.10235(6) 0.46966(5) 0.0199(3) Uani 1 1 d D . . H8 H 0.3721 0.1077 0.5066 0.024 Uiso 1 1 calc R . . C9 C 0.20081(14) 0.11065(7) 0.46007(6) 0.0226(3) Uani 1 1 d D . . H9 H 0.1424 0.1206 0.4906 0.027 Uiso 1 1 calc R . . C10 C 0.14877(13) 0.10455(7) 0.40613(6) 0.0227(3) Uani 1 1 d D . . H10 H 0.0555 0.1112 0.3994 0.027 Uiso 1 1 calc R . . C11 C 0.23519(13) 0.08857(7) 0.36230(5) 0.0207(3) Uani 1 1 d D . . H11 H 0.2001 0.0850 0.3253 0.025 Uiso 1 1 calc R . . C12 C 0.37236(13) 0.07761(6) 0.37112(5) 0.0179(2) Uani 1 1 d D . . C13 C 0.46271(13) 0.05798(6) 0.32247(5) 0.0190(3) Uani 1 1 d . . . H13 H 0.4145 0.0225 0.2997 0.023 Uiso 1 1 calc R . . C14 C 0.61136(13) 0.08778(7) 0.49163(5) 0.0199(3) Uani 1 1 d . . . H14 H 0.5847 0.0554 0.5194 0.024 Uiso 1 1 calc R . . C15 C 0.69163(12) 0.13967(6) 0.50701(5) 0.0178(2) Uani 1 1 d . . . C21 C 0.48821(13) 0.11990(7) 0.28444(5) 0.0194(3) Uani 1 1 d . . . C22 C 0.41648(14) 0.12672(8) 0.23465(6) 0.0256(3) Uani 1 1 d D . . H22 H 0.3547 0.0919 0.2237 0.031 Uiso 1 1 calc R . . C23 C 0.43473(15) 0.18423(8) 0.20083(6) 0.0288(3) Uani 1 1 d D . . H23 H 0.3847 0.1888 0.1670 0.035 Uiso 1 1 calc R . . C24 C 0.52516(14) 0.23475(7) 0.21605(6) 0.0263(3) Uani 1 1 d D . . H24 H 0.5372 0.2740 0.1929 0.032 Uiso 1 1 calc R . . C25 C 0.59846(14) 0.22783(7) 0.26538(6) 0.0262(3) Uani 1 1 d D . . H25 H 0.6614 0.2623 0.2759 0.031 Uiso 1 1 calc R . . C26 C 0.57975(14) 0.17047(7) 0.29943(6) 0.0233(3) Uani 1 1 d D . . H26 H 0.6300 0.1659 0.3332 0.028 Uiso 1 1 calc R . . C31 C 0.72912(12) 0.19651(6) 0.46819(5) 0.0174(2) Uani 1 1 d . . . C32 C 0.63111(13) 0.23487(6) 0.44004(5) 0.0191(3) Uani 1 1 d D . . H32 H 0.5389 0.2230 0.4439 0.023 Uiso 1 1 calc R . . C33 C 0.66776(14) 0.29028(7) 0.40638(5) 0.0220(3) Uani 1 1 d D . . H33 H 0.6004 0.3165 0.3879 0.026 Uiso 1 1 calc R . . C34 C 0.80251(14) 0.30738(7) 0.39979(5) 0.0230(3) Uani 1 1 d D . . H34 H 0.8275 0.3452 0.3768 0.028 Uiso 1 1 calc R . . C35 C 0.90048(13) 0.26898(7) 0.42695(5) 0.0227(3) Uani 1 1 d D . . H35 H 0.9928 0.2801 0.4220 0.027 Uiso 1 1 calc R . . C36 C 0.86437(13) 0.21448(7) 0.46129(5) 0.0204(3) Uani 1 1 d D . . H36 H 0.9321 0.1891 0.4803 0.025 Uiso 1 1 calc R . . C41 C 0.74571(12) 0.14324(6) 0.56534(5) 0.0181(3) Uani 1 1 d . . . C42 C 0.76984(12) 0.20710(7) 0.59099(5) 0.0194(3) Uani 1 1 d D . . H42 H 0.7557 0.2482 0.5703 0.023 Uiso 1 1 calc R . . C43 C 0.81406(13) 0.21098(7) 0.64615(6) 0.0222(3) Uani 1 1 d D . . H43 H 0.8291 0.2546 0.6630 0.027 Uiso 1 1 calc R . . C44 C 0.83638(14) 0.15120(7) 0.67684(6) 0.0243(3) Uani 1 1 d D . . H44 H 0.8662 0.1537 0.7147 0.029 Uiso 1 1 calc R . . C45 C 0.81476(15) 0.08790(7) 0.65166(6) 0.0254(3) Uani 1 1 d D . . H45 H 0.8301 0.0470 0.6725 0.031 Uiso 1 1 calc R . . C46 C 0.77089(14) 0.08361(7) 0.59641(6) 0.0224(3) Uani 1 1 d D . . H46 H 0.7579 0.0398 0.5796 0.027 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 0.0184(5) 0.0188(5) 0.0201(5) -0.0019(4) -0.0032(4) -0.0003(4) C1 0.0226(6) 0.0163(6) 0.0211(6) 0.0027(5) 0.0023(5) -0.0003(5) C2 0.0333(7) 0.0217(6) 0.0220(6) 0.0018(5) 0.0042(5) 0.0019(6) C3 0.0323(7) 0.0241(7) 0.0318(7) 0.0030(6) 0.0112(6) 0.0085(6) C4 0.0231(7) 0.0249(7) 0.0390(8) 0.0062(6) 0.0031(6) 0.0060(5) C5 0.0234(7) 0.0222(6) 0.0290(7) 0.0017(5) -0.0021(5) 0.0007(5) C6 0.0211(6) 0.0146(5) 0.0232(6) 0.0019(5) 0.0018(5) -0.0007(5) C7 0.0190(6) 0.0128(5) 0.0212(6) 0.0009(4) -0.0015(5) -0.0012(4) C8 0.0247(6) 0.0178(6) 0.0172(6) -0.0019(4) -0.0016(5) 0.0003(5) C9 0.0240(6) 0.0201(6) 0.0238(6) -0.0006(5) 0.0051(5) 0.0016(5) C10 0.0180(6) 0.0207(6) 0.0295(7) 0.0018(5) -0.0003(5) 0.0005(5) C11 0.0221(6) 0.0193(6) 0.0205(6) 0.0025(5) -0.0033(5) -0.0010(5) C12 0.0204(6) 0.0149(5) 0.0185(6) 0.0019(4) 0.0004(5) -0.0017(5) C13 0.0219(6) 0.0184(6) 0.0168(6) -0.0006(4) -0.0005(5) -0.0012(5) C14 0.0211(6) 0.0190(6) 0.0196(6) 0.0020(5) -0.0028(5) 0.0008(5) C15 0.0160(6) 0.0177(6) 0.0197(6) -0.0003(4) -0.0008(4) 0.0034(4) C21 0.0197(6) 0.0212(6) 0.0173(6) 0.0006(5) 0.0032(5) 0.0023(5) C22 0.0243(6) 0.0299(7) 0.0227(6) 0.0019(5) -0.0017(5) -0.0037(6) C23 0.0259(7) 0.0371(8) 0.0232(7) 0.0074(6) -0.0015(5) 0.0014(6) C24 0.0254(7) 0.0287(7) 0.0248(7) 0.0089(5) 0.0064(5) 0.0030(5) C25 0.0273(7) 0.0249(7) 0.0264(7) 0.0024(5) 0.0024(5) -0.0037(5) C26 0.0246(6) 0.0256(7) 0.0197(6) 0.0010(5) -0.0012(5) -0.0016(5) C31 0.0188(6) 0.0169(6) 0.0164(5) -0.0024(4) -0.0006(4) 0.0008(5) C32 0.0180(6) 0.0187(6) 0.0207(6) -0.0010(5) -0.0027(5) 0.0000(5) C33 0.0260(6) 0.0201(6) 0.0200(6) -0.0006(5) -0.0046(5) 0.0008(5) C34 0.0305(7) 0.0211(6) 0.0173(6) -0.0008(5) 0.0016(5) -0.0061(5) C35 0.0196(6) 0.0279(7) 0.0205(6) -0.0056(5) 0.0037(5) -0.0052(5) C36 0.0180(6) 0.0238(6) 0.0195(6) -0.0038(5) -0.0014(5) 0.0020(5) C41 0.0153(5) 0.0193(6) 0.0197(6) -0.0003(5) -0.0003(5) 0.0012(4) C42 0.0163(6) 0.0184(6) 0.0235(6) 0.0010(5) 0.0004(5) 0.0011(5) C43 0.0191(6) 0.0232(6) 0.0242(6) -0.0056(5) 0.0007(5) -0.0014(5) C44 0.0242(6) 0.0305(7) 0.0183(6) -0.0015(5) -0.0019(5) -0.0011(5) C45 0.0294(7) 0.0240(6) 0.0229(7) 0.0044(5) -0.0040(5) 0.0013(5) C46 0.0247(6) 0.0190(6) 0.0233(6) 0.0001(5) -0.0029(5) -0.0005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.4105(16) . ? N1 C7 1.4125(16) . ? N1 C14 1.4309(16) . ? C1 C2 1.3918(18) . ? C1 C6 1.4053(18) . ? C1 C13 1.5166(18) . ? C2 C3 1.389(2) . ? C3 C4 1.385(2) . ? C4 C5 1.386(2) . ? C5 C6 1.4029(18) . ? C7 C8 1.3995(18) . ? C7 C12 1.4035(17) . ? C8 C9 1.3858(19) . ? C9 C10 1.3898(19) . ? C10 C11 1.3872(19) . ? C11 C12 1.3961(18) . ? C12 C13 1.5150(17) . ? C13 C21 1.5284(17) . ? C14 C15 1.3381(18) . ? C15 C31 1.4888(17) . ? C15 C41 1.4910(17) . ? C21 C26 1.3870(19) . ? C21 C22 1.3898(18) . ? C22 C23 1.391(2) . ? C23 C24 1.381(2) . ? C24 C25 1.389(2) . ? C25 C26 1.3920(19) . ? C31 C32 1.3985(17) . ? C31 C36 1.3991(17) . ? C32 C33 1.3920(18) . ? C33 C34 1.3894(19) . ? C34 C35 1.388(2) . ? C35 C36 1.3863(19) . ? C41 C46 1.3988(18) . ? C41 C42 1.4052(17) . ? C42 C43 1.3870(18) . ? C43 C44 1.3915(19) . ? C44 C45 1.3867(19) . ? C45 C46 1.3885(19) . ? 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 C6 N1 C7 119.35(10) . . ? C6 N1 C14 118.96(11) . . ? C7 N1 C14 117.92(11) . . ? C2 C1 C6 118.87(12) . . ? C2 C1 C13 119.82(12) . . ? C6 C1 C13 121.25(11) . . ? C3 C2 C1 121.78(13) . . ? C4 C3 C2 118.88(13) . . ? C3 C4 C5 120.73(13) . . ? C4 C5 C6 120.36(13) . . ? C5 C6 C1 119.28(12) . . ? C5 C6 N1 120.87(12) . . ? C1 C6 N1 119.85(11) . . ? C8 C7 C12 119.43(11) . . ? C8 C7 N1 120.27(11) . . ? C12 C7 N1 120.30(11) . . ? C9 C8 C7 120.58(12) . . ? C8 C9 C10 120.47(12) . . ? C11 C10 C9 118.93(12) . . ? C10 C11 C12 121.74(12) . . ? C11 C12 C7 118.78(12) . . ? C11 C12 C13 120.17(11) . . ? C7 C12 C13 121.05(11) . . ? C12 C13 C1 111.02(10) . . ? C12 C13 C21 110.66(10) . . ? C1 C13 C21 111.90(10) . . ? C15 C14 N1 123.16(12) . . ? C14 C15 C31 122.68(11) . . ? C14 C15 C41 120.34(11) . . ? C31 C15 C41 116.97(11) . . ? C26 C21 C22 119.25(12) . . ? C26 C21 C13 121.04(11) . . ? C22 C21 C13 119.70(12) . . ? C21 C22 C23 120.25(13) . . ? C24 C23 C22 120.39(13) . . ? C23 C24 C25 119.65(13) . . ? C24 C25 C26 120.02(13) . . ? C21 C26 C25 120.44(12) . . ? C32 C31 C36 118.69(12) . . ? C32 C31 C15 121.31(11) . . ? C36 C31 C15 119.95(11) . . ? C33 C32 C31 120.46(12) . . ? C34 C33 C32 120.20(12) . . ? C35 C34 C33 119.68(12) . . ? C36 C35 C34 120.34(12) . . ? C35 C36 C31 120.62(12) . . ? C46 C41 C42 118.23(11) . . ? C46 C41 C15 121.24(11) . . ? C42 C41 C15 120.51(11) . . ? C43 C42 C41 120.92(12) . . ? C42 C43 C44 120.15(12) . . ? C45 C44 C43 119.39(12) . . ? C44 C45 C46 120.78(12) . . ? C45 C46 C41 120.50(12) . . ? 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 C6 C1 C2 C3 -3.0(2) . . . . ? C13 C1 C2 C3 174.11(12) . . . . ? C1 C2 C3 C4 0.4(2) . . . . ? C2 C3 C4 C5 1.3(2) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C4 C5 C6 C1 -2.2(2) . . . . ? C4 C5 C6 N1 177.58(12) . . . . ? C2 C1 C6 C5 3.89(19) . . . . ? C13 C1 C6 C5 -173.22(12) . . . . ? C2 C1 C6 N1 -175.92(12) . . . . ? C13 C1 C6 N1 6.98(18) . . . . ? C7 N1 C6 C5 -162.46(12) . . . . ? C14 N1 C6 C5 -4.77(18) . . . . ? C7 N1 C6 C1 17.34(17) . . . . ? C14 N1 C6 C1 175.03(11) . . . . ? C6 N1 C7 C8 158.28(11) . . . . ? C14 N1 C7 C8 0.36(17) . . . . ? C6 N1 C7 C12 -21.99(17) . . . . ? C14 N1 C7 C12 -179.91(11) . . . . ? C12 C7 C8 C9 -0.59(18) . . . . ? N1 C7 C8 C9 179.14(12) . . . . ? C7 C8 C9 C10 -1.5(2) . . . . ? C8 C9 C10 C11 1.4(2) . . . . ? C9 C10 C11 C12 0.85(19) . . . . ? C10 C11 C12 C7 -2.91(19) . . . . ? C10 C11 C12 C13 178.02(12) . . . . ? C8 C7 C12 C11 2.74(18) . . . . ? N1 C7 C12 C11 -177.00(11) . . . . ? C8 C7 C12 C13 -178.19(11) . . . . ? N1 C7 C12 C13 2.07(17) . . . . ? C11 C12 C13 C1 -161.25(11) . . . . ? C7 C12 C13 C1 19.70(16) . . . . ? C11 C12 C13 C21 73.87(14) . . . . ? C7 C12 C13 C21 -105.19(13) . . . . ? C2 C1 C13 C12 158.64(12) . . . . ? C6 C1 C13 C12 -24.28(16) . . . . ? C2 C1 C13 C21 -77.18(15) . . . . ? C6 C1 C13 C21 99.90(14) . . . . ? C6 N1 C14 C15 88.33(16) . . . . ? C7 N1 C14 C15 -113.66(14) . . . . ? N1 C14 C15 C31 5.7(2) . . . . ? N1 C14 C15 C41 -175.46(11) . . . . ? C12 C13 C21 C26 77.87(15) . . . . ? C1 C13 C21 C26 -46.51(16) . . . . ? C12 C13 C21 C22 -100.58(14) . . . . ? C1 C13 C21 C22 135.03(13) . . . . ? C26 C21 C22 C23 -1.1(2) . . . . ? C13 C21 C22 C23 177.35(12) . . . . ? C21 C22 C23 C24 0.7(2) . . . . ? C22 C23 C24 C25 0.2(2) . . . . ? C23 C24 C25 C26 -0.5(2) . . . . ? C22 C21 C26 C25 0.8(2) . . . . ? C13 C21 C26 C25 -177.68(12) . . . . ? C24 C25 C26 C21 0.1(2) . . . . ? C14 C15 C31 C32 53.81(18) . . . . ? C41 C15 C31 C32 -125.04(12) . . . . ? C14 C15 C31 C36 -129.12(14) . . . . ? C41 C15 C31 C36 52.03(16) . . . . ? C36 C31 C32 C33 -0.72(18) . . . . ? C15 C31 C32 C33 176.39(11) . . . . ? C31 C32 C33 C34 0.93(19) . . . . ? C32 C33 C34 C35 -0.03(19) . . . . ? C33 C34 C35 C36 -1.07(19) . . . . ? C34 C35 C36 C31 1.29(19) . . . . ? C32 C31 C36 C35 -0.38(18) . . . . ? C15 C31 C36 C35 -177.53(11) . . . . ? C14 C15 C41 C46 30.40(18) . . . . ? C31 C15 C41 C46 -150.72(12) . . . . ? C14 C15 C41 C42 -148.15(13) . . . . ? C31 C15 C41 C42 30.73(17) . . . . ? C46 C41 C42 C43 -1.68(19) . . . . ? C15 C41 C42 C43 176.91(11) . . . . ? C41 C42 C43 C44 0.57(19) . . . . ? C42 C43 C44 C45 0.4(2) . . . . ? C43 C44 C45 C46 -0.2(2) . . . . ? C44 C45 C46 C41 -1.0(2) . . . . ? C42 C41 C46 C45 1.9(2) . . . . ? C15 C41 C46 C45 -176.71(12) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.357 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.049 #===END data_ivbbf5s_compound_20b _database_code_depnum_ccdc_archive 'CCDC 779908' #TrackingRef '- Alajarin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H37 N3' _chemical_formula_weight 535.71 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' _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 8.6296(5) _cell_length_b 11.3810(7) _cell_length_c 15.5193(9) _cell_angle_alpha 104.522(2) _cell_angle_beta 102.416(2) _cell_angle_gamma 96.090(2) _cell_volume 1420.21(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3295 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.63 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9813 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details SADABS _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 SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16506 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.24 _reflns_number_total 6359 _reflns_number_gt 4997 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0511P)^2^+0.5453P] 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 'Me rigid, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6359 _refine_ls_number_parameters 375 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.015 _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 0.54182(15) 0.90087(12) 0.13613(9) 0.0150(3) Uani 1 1 d . . . N2 N 0.74806(17) 0.44145(13) 0.32262(10) 0.0209(3) Uani 1 1 d . . . N3 N -0.16902(16) 0.61873(13) -0.05958(9) 0.0214(3) Uani 1 1 d . . . C1 C 0.74789(18) 0.99804(14) 0.28024(11) 0.0150(3) Uani 1 1 d . . . C2 C 0.89633(19) 1.07150(15) 0.32607(11) 0.0175(3) Uani 1 1 d . . . H2 H 0.9338 1.0876 0.3908 0.021 Uiso 1 1 calc R . . C3 C 0.98998(19) 1.12143(15) 0.27738(12) 0.0200(4) Uani 1 1 d . . . H3 H 1.0913 1.1719 0.3088 0.024 Uiso 1 1 calc R . . C4 C 0.93569(19) 1.09764(15) 0.18285(12) 0.0188(3) Uani 1 1 d . . . H4 H 1.0012 1.1317 0.1502 0.023 Uiso 1 1 calc R . . C5 C 0.78693(19) 1.02474(15) 0.13476(11) 0.0173(3) Uani 1 1 d . . . C6 C 0.69209(18) 0.97640(14) 0.18519(11) 0.0147(3) Uani 1 1 d . . . C7 C 0.64501(18) 0.93538(14) 0.32841(11) 0.0147(3) Uani 1 1 d . . . H7 H 0.6720 0.9857 0.3942 0.018 Uiso 1 1 calc R . . C8 C 0.46253(18) 0.93995(14) 0.28440(10) 0.0141(3) Uani 1 1 d . . . C9 C 0.43364(18) 0.88152(14) 0.17950(11) 0.0143(3) Uani 1 1 d . . . C10 C 0.7308(2) 1.00101(16) 0.03243(11) 0.0213(4) Uani 1 1 d . . . H10A H 0.6493 1.0519 0.0185 0.026 Uiso 1 1 calc R . . H10B H 0.6841 0.9138 0.0041 0.026 Uiso 1 1 calc R . . H10C H 0.8224 1.0218 0.0079 0.026 Uiso 1 1 calc R . . C21 C 0.68499(18) 0.80801(14) 0.32712(11) 0.0150(3) Uani 1 1 d D . . C22 C 0.70314(19) 0.76779(15) 0.40624(11) 0.0181(3) Uani 1 1 d D . . H22 H 0.6978 0.8236 0.4620 0.022 Uiso 1 1 calc R . . C23 C 0.72851(19) 0.64993(15) 0.40648(11) 0.0196(4) Uani 1 1 d D . . H23 H 0.7416 0.6272 0.4622 0.023 Uiso 1 1 calc R . . C24 C 0.73520(18) 0.56319(15) 0.32553(11) 0.0176(3) Uani 1 1 d D . . C25 C 0.7239(2) 0.60456(15) 0.24677(11) 0.0193(4) Uani 1 1 d D . . H25 H 0.7326 0.5498 0.1913 0.023 Uiso 1 1 calc R . . C26 C 0.70056(19) 0.72345(15) 0.24826(11) 0.0185(3) Uani 1 1 d D . . H26 H 0.6949 0.7483 0.1938 0.022 Uiso 1 1 calc R . . C27 C 0.8399(2) 0.41332(17) 0.40237(13) 0.0297(4) Uani 1 1 d . . . H27A H 0.9552 0.4356 0.4078 0.036 Uiso 1 1 calc R . . H27B H 0.8140 0.3250 0.3956 0.036 Uiso 1 1 calc R . . H27C H 0.8128 0.4603 0.4577 0.036 Uiso 1 1 calc R . . C28 C 0.7449(2) 0.35377(16) 0.23639(12) 0.0250(4) Uani 1 1 d . . . H28A H 0.6568 0.3623 0.1879 0.030 Uiso 1 1 calc R . . H28B H 0.7282 0.2700 0.2425 0.030 Uiso 1 1 calc R . . H28C H 0.8475 0.3696 0.2204 0.030 Uiso 1 1 calc R . . C31 C 0.35027(18) 0.87292(15) 0.32829(10) 0.0146(3) Uani 1 1 d D . . C32 C 0.33736(19) 0.74587(15) 0.31491(11) 0.0176(3) Uani 1 1 d D . . H32 H 0.3989 0.7010 0.2786 0.021 Uiso 1 1 calc R . . C33 C 0.23632(19) 0.68377(15) 0.35365(11) 0.0198(4) Uani 1 1 d D . . H33 H 0.2318 0.5977 0.3448 0.024 Uiso 1 1 calc R . . C34 C 0.14185(19) 0.74621(16) 0.40514(11) 0.0210(4) Uani 1 1 d D . . H34 H 0.0726 0.7038 0.4316 0.025 Uiso 1 1 calc R . . C35 C 0.15055(19) 0.87113(16) 0.41706(11) 0.0194(4) Uani 1 1 d D . . H35 H 0.0850 0.9148 0.4511 0.023 Uiso 1 1 calc R . . C36 C 0.25379(19) 0.93393(16) 0.37998(11) 0.0173(3) Uani 1 1 d D . . H36 H 0.2589 1.0203 0.3900 0.021 Uiso 1 1 calc R . . C41 C 0.44534(18) 1.07732(15) 0.30046(11) 0.0156(3) Uani 1 1 d D . . C42 C 0.49652(19) 1.15967(15) 0.38897(11) 0.0182(3) Uani 1 1 d D . . H42 H 0.5455 1.1312 0.4391 0.022 Uiso 1 1 calc R . . C43 C 0.4769(2) 1.28191(16) 0.40458(12) 0.0217(4) Uani 1 1 d D . . H43 H 0.5112 1.3360 0.4652 0.026 Uiso 1 1 calc R . . C44 C 0.4074(2) 1.32574(15) 0.33225(12) 0.0214(4) Uani 1 1 d D . . H44 H 0.3944 1.4096 0.3430 0.026 Uiso 1 1 calc R . . C45 C 0.35705(19) 1.24608(16) 0.24438(12) 0.0206(4) Uani 1 1 d D . . H45 H 0.3098 1.2754 0.1944 0.025 Uiso 1 1 calc R . . C46 C 0.37528(19) 1.12346(15) 0.22895(11) 0.0171(3) Uani 1 1 d D . . H46 H 0.3392 1.0697 0.1683 0.021 Uiso 1 1 calc R . . C51 C 0.27679(19) 0.80711(14) 0.12236(11) 0.0149(3) Uani 1 1 d D . . C52 C 0.12970(19) 0.82832(15) 0.14250(11) 0.0164(3) Uani 1 1 d D . . H52 H 0.1302 0.8871 0.1982 0.020 Uiso 1 1 calc R . . C53 C -0.01588(19) 0.76627(15) 0.08366(11) 0.0174(3) Uani 1 1 d D . . H53 H -0.1131 0.7835 0.0995 0.021 Uiso 1 1 calc R . . C54 C -0.02286(19) 0.67792(15) 0.00052(11) 0.0165(3) Uani 1 1 d D . . C55 C 0.12467(19) 0.65478(15) -0.01914(11) 0.0178(3) Uani 1 1 d D . . H55 H 0.1248 0.5941 -0.0737 0.021 Uiso 1 1 calc R . . C56 C 0.26897(19) 0.71895(15) 0.03973(11) 0.0176(3) Uani 1 1 d D . . H56 H 0.3664 0.7028 0.0237 0.021 Uiso 1 1 calc R . . C57 C -0.3146(2) 0.61662(17) -0.02658(12) 0.0232(4) Uani 1 1 d . . . H57A H -0.2999 0.5818 0.0257 0.028 Uiso 1 1 calc R . . H57B H -0.4054 0.5659 -0.0761 0.028 Uiso 1 1 calc R . . H57C H -0.3364 0.7007 -0.0072 0.028 Uiso 1 1 calc R . . C58 C -0.1719(2) 0.52581(16) -0.14355(11) 0.0218(4) Uani 1 1 d . . . H58A H -0.1069 0.5610 -0.1785 0.026 Uiso 1 1 calc R . . H58B H -0.2831 0.4979 -0.1807 0.026 Uiso 1 1 calc R . . H58C H -0.1275 0.4557 -0.1281 0.026 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 0.0156(6) 0.0145(7) 0.0154(7) 0.0046(5) 0.0039(5) 0.0036(5) N2 0.0231(7) 0.0176(7) 0.0236(8) 0.0073(6) 0.0067(6) 0.0050(6) N3 0.0175(7) 0.0243(8) 0.0168(7) -0.0003(6) 0.0017(6) -0.0002(6) C1 0.0146(7) 0.0144(8) 0.0179(8) 0.0056(6) 0.0057(6) 0.0053(6) C2 0.0167(8) 0.0174(8) 0.0183(8) 0.0048(7) 0.0036(6) 0.0042(6) C3 0.0145(8) 0.0176(8) 0.0273(9) 0.0060(7) 0.0044(7) 0.0032(6) C4 0.0169(8) 0.0192(8) 0.0253(9) 0.0109(7) 0.0095(7) 0.0056(7) C5 0.0178(8) 0.0174(8) 0.0198(9) 0.0065(7) 0.0074(7) 0.0082(7) C6 0.0151(7) 0.0137(8) 0.0157(8) 0.0036(6) 0.0043(6) 0.0049(6) C7 0.0145(7) 0.0166(8) 0.0120(8) 0.0029(6) 0.0022(6) 0.0026(6) C8 0.0133(7) 0.0146(8) 0.0140(8) 0.0035(6) 0.0033(6) 0.0027(6) C9 0.0168(8) 0.0121(7) 0.0154(8) 0.0053(6) 0.0038(6) 0.0050(6) C10 0.0212(8) 0.0265(9) 0.0194(9) 0.0100(7) 0.0079(7) 0.0037(7) C21 0.0106(7) 0.0164(8) 0.0176(8) 0.0050(6) 0.0029(6) 0.0012(6) C22 0.0173(8) 0.0201(8) 0.0159(8) 0.0030(7) 0.0050(7) 0.0026(7) C23 0.0189(8) 0.0237(9) 0.0179(8) 0.0095(7) 0.0046(7) 0.0028(7) C24 0.0112(7) 0.0201(8) 0.0215(9) 0.0069(7) 0.0037(6) 0.0014(6) C25 0.0207(8) 0.0204(9) 0.0178(8) 0.0045(7) 0.0073(7) 0.0047(7) C26 0.0207(8) 0.0202(9) 0.0178(8) 0.0086(7) 0.0068(7) 0.0060(7) C27 0.0328(10) 0.0246(10) 0.0325(11) 0.0130(8) 0.0024(8) 0.0083(8) C28 0.0283(9) 0.0198(9) 0.0290(10) 0.0071(8) 0.0098(8) 0.0071(7) C31 0.0123(7) 0.0190(8) 0.0104(8) 0.0037(6) 0.0001(6) 0.0006(6) C32 0.0155(8) 0.0195(8) 0.0166(8) 0.0036(7) 0.0034(6) 0.0026(6) C33 0.0196(8) 0.0170(8) 0.0197(9) 0.0056(7) 0.0002(7) -0.0011(7) C34 0.0157(8) 0.0300(10) 0.0181(9) 0.0105(7) 0.0035(7) -0.0004(7) C35 0.0165(8) 0.0280(9) 0.0140(8) 0.0055(7) 0.0045(6) 0.0053(7) C36 0.0153(8) 0.0206(8) 0.0149(8) 0.0041(7) 0.0021(6) 0.0034(6) C41 0.0122(7) 0.0170(8) 0.0184(8) 0.0046(6) 0.0066(6) 0.0015(6) C42 0.0168(8) 0.0192(8) 0.0180(8) 0.0042(7) 0.0043(7) 0.0032(7) C43 0.0197(8) 0.0190(9) 0.0229(9) -0.0011(7) 0.0071(7) 0.0012(7) C44 0.0207(8) 0.0135(8) 0.0309(10) 0.0050(7) 0.0103(7) 0.0025(7) C45 0.0179(8) 0.0223(9) 0.0258(9) 0.0119(7) 0.0073(7) 0.0052(7) C46 0.0146(7) 0.0196(8) 0.0172(8) 0.0050(7) 0.0047(6) 0.0019(6) C51 0.0165(8) 0.0153(8) 0.0135(8) 0.0060(6) 0.0025(6) 0.0025(6) C52 0.0195(8) 0.0156(8) 0.0128(8) 0.0020(6) 0.0034(6) 0.0036(6) C53 0.0164(8) 0.0195(8) 0.0174(8) 0.0057(7) 0.0054(6) 0.0038(7) C54 0.0176(8) 0.0162(8) 0.0145(8) 0.0051(6) 0.0014(6) 0.0007(6) C55 0.0214(8) 0.0170(8) 0.0126(8) 0.0003(6) 0.0042(7) 0.0029(7) C56 0.0171(8) 0.0207(8) 0.0161(8) 0.0051(7) 0.0061(6) 0.0042(7) C57 0.0163(8) 0.0256(9) 0.0227(9) 0.0024(7) 0.0010(7) 0.0008(7) C58 0.0220(9) 0.0206(9) 0.0178(9) 0.0021(7) -0.0006(7) 0.0007(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 C9 1.294(2) . ? N1 C6 1.418(2) . ? N2 C24 1.392(2) . ? N2 C27 1.447(2) . ? N2 C28 1.448(2) . ? N3 C54 1.383(2) . ? N3 C58 1.451(2) . ? N3 C57 1.455(2) . ? C1 C2 1.389(2) . ? C1 C6 1.398(2) . ? C1 C7 1.508(2) . ? C2 C3 1.388(2) . ? C3 C4 1.387(2) . ? C4 C5 1.395(2) . ? C5 C6 1.407(2) . ? C5 C10 1.502(2) . ? C7 C21 1.522(2) . ? C7 C8 1.588(2) . ? C8 C31 1.540(2) . ? C8 C41 1.549(2) . ? C8 C9 1.550(2) . ? C9 C51 1.483(2) . ? C21 C26 1.396(2) . ? C21 C22 1.399(2) . ? C22 C23 1.383(2) . ? C23 C24 1.406(2) . ? C24 C25 1.404(2) . ? C25 C26 1.384(2) . ? C31 C36 1.396(2) . ? C31 C32 1.397(2) . ? C32 C33 1.389(2) . ? C33 C34 1.388(2) . ? C34 C35 1.379(2) . ? C35 C36 1.388(2) . ? C41 C46 1.394(2) . ? C41 C42 1.402(2) . ? C42 C43 1.386(2) . ? C43 C44 1.387(2) . ? C44 C45 1.383(2) . ? C45 C46 1.387(2) . ? C51 C56 1.400(2) . ? C51 C52 1.402(2) . ? C52 C53 1.381(2) . ? C53 C54 1.408(2) . ? C54 C55 1.408(2) . ? C55 C56 1.379(2) . ? 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 C9 N1 C6 119.74(13) . . ? C24 N2 C27 119.79(15) . . ? C24 N2 C28 119.85(14) . . ? C27 N2 C28 113.58(14) . . ? C54 N3 C58 119.54(14) . . ? C54 N3 C57 119.72(14) . . ? C58 N3 C57 117.45(14) . . ? C2 C1 C6 119.71(15) . . ? C2 C1 C7 122.52(14) . . ? C6 C1 C7 117.72(14) . . ? C3 C2 C1 120.06(15) . . ? C4 C3 C2 120.04(15) . . ? C3 C4 C5 121.37(15) . . ? C4 C5 C6 117.97(15) . . ? C4 C5 C10 120.23(15) . . ? C6 C5 C10 121.80(15) . . ? C1 C6 C5 120.81(15) . . ? C1 C6 N1 121.16(14) . . ? C5 C6 N1 117.97(14) . . ? C1 C7 C21 110.69(12) . . ? C1 C7 C8 107.67(12) . . ? C21 C7 C8 115.84(13) . . ? C31 C8 C41 111.55(12) . . ? C31 C8 C9 113.43(13) . . ? C41 C8 C9 107.87(12) . . ? C31 C8 C7 110.27(12) . . ? C41 C8 C7 107.36(12) . . ? C9 C8 C7 106.03(12) . . ? N1 C9 C51 116.28(14) . . ? N1 C9 C8 121.80(14) . . ? C51 C9 C8 121.81(13) . . ? C26 C21 C22 116.03(15) . . ? C26 C21 C7 123.21(14) . . ? C22 C21 C7 120.73(14) . . ? C23 C22 C21 122.58(15) . . ? C22 C23 C24 120.98(15) . . ? N2 C24 C25 121.42(15) . . ? N2 C24 C23 121.88(15) . . ? C25 C24 C23 116.68(15) . . ? C26 C25 C24 121.37(16) . . ? C25 C26 C21 122.21(15) . . ? C36 C31 C32 117.09(15) . . ? C36 C31 C8 122.37(14) . . ? C32 C31 C8 120.51(14) . . ? C33 C32 C31 121.32(15) . . ? C34 C33 C32 120.67(16) . . ? C35 C34 C33 118.60(15) . . ? C34 C35 C36 120.89(15) . . ? C35 C36 C31 121.40(16) . . ? C46 C41 C42 117.41(15) . . ? C46 C41 C8 121.93(14) . . ? C42 C41 C8 120.64(14) . . ? C43 C42 C41 121.12(15) . . ? C42 C43 C44 120.39(16) . . ? C45 C44 C43 119.32(15) . . ? C44 C45 C46 120.25(16) . . ? C45 C46 C41 121.51(16) . . ? C56 C51 C52 116.65(14) . . ? C56 C51 C9 120.27(14) . . ? C52 C51 C9 122.80(14) . . ? C53 C52 C51 121.87(15) . . ? C52 C53 C54 121.18(15) . . ? N3 C54 C55 121.89(14) . . ? N3 C54 C53 120.99(14) . . ? C55 C54 C53 117.11(14) . . ? C56 C55 C54 120.95(15) . . ? C55 C56 C51 122.22(15) . . ? 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 C6 C1 C2 C3 -1.1(2) . . . . ? C7 C1 C2 C3 176.44(14) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 0.5(2) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C3 C4 C5 C10 179.70(15) . . . . ? C2 C1 C6 C5 2.2(2) . . . . ? C7 C1 C6 C5 -175.49(13) . . . . ? C2 C1 C6 N1 179.38(14) . . . . ? C7 C1 C6 N1 1.7(2) . . . . ? C4 C5 C6 C1 -1.9(2) . . . . ? C10 C5 C6 C1 178.96(14) . . . . ? C4 C5 C6 N1 -179.15(13) . . . . ? C10 C5 C6 N1 1.7(2) . . . . ? C9 N1 C6 C1 21.0(2) . . . . ? C9 N1 C6 C5 -161.77(14) . . . . ? C2 C1 C7 C21 -90.03(18) . . . . ? C6 C1 C7 C21 87.56(16) . . . . ? C2 C1 C7 C8 142.42(14) . . . . ? C6 C1 C7 C8 -39.99(18) . . . . ? C1 C7 C8 C31 177.89(12) . . . . ? C21 C7 C8 C31 53.39(17) . . . . ? C1 C7 C8 C41 -60.39(15) . . . . ? C21 C7 C8 C41 175.12(13) . . . . ? C1 C7 C8 C9 54.73(15) . . . . ? C21 C7 C8 C9 -69.77(16) . . . . ? C6 N1 C9 C51 176.79(13) . . . . ? C6 N1 C9 C8 0.7(2) . . . . ? C31 C8 C9 N1 -159.82(14) . . . . ? C41 C8 C9 N1 76.10(17) . . . . ? C7 C8 C9 N1 -38.66(18) . . . . ? C31 C8 C9 C51 24.26(19) . . . . ? C41 C8 C9 C51 -99.82(16) . . . . ? C7 C8 C9 C51 145.42(14) . . . . ? C1 C7 C21 C26 -46.7(2) . . . . ? C8 C7 C21 C26 76.19(19) . . . . ? C1 C7 C21 C22 135.41(15) . . . . ? C8 C7 C21 C22 -101.67(17) . . . . ? C26 C21 C22 C23 -2.5(2) . . . . ? C7 C21 C22 C23 175.46(14) . . . . ? C21 C22 C23 C24 -0.9(2) . . . . ? C27 N2 C24 C25 147.36(16) . . . . ? C28 N2 C24 C25 -2.0(2) . . . . ? C27 N2 C24 C23 -34.4(2) . . . . ? C28 N2 C24 C23 176.33(15) . . . . ? C22 C23 C24 N2 -174.91(15) . . . . ? C22 C23 C24 C25 3.4(2) . . . . ? N2 C24 C25 C26 175.71(15) . . . . ? C23 C24 C25 C26 -2.7(2) . . . . ? C24 C25 C26 C21 -0.8(3) . . . . ? C22 C21 C26 C25 3.4(2) . . . . ? C7 C21 C26 C25 -174.59(14) . . . . ? C41 C8 C31 C36 -3.3(2) . . . . ? C9 C8 C31 C36 -125.39(15) . . . . ? C7 C8 C31 C36 115.87(15) . . . . ? C41 C8 C31 C32 174.50(14) . . . . ? C9 C8 C31 C32 52.45(19) . . . . ? C7 C8 C31 C32 -66.30(18) . . . . ? C36 C31 C32 C33 -1.8(2) . . . . ? C8 C31 C32 C33 -179.76(14) . . . . ? C31 C32 C33 C34 1.6(2) . . . . ? C32 C33 C34 C35 -0.1(2) . . . . ? C33 C34 C35 C36 -1.2(2) . . . . ? C34 C35 C36 C31 1.0(2) . . . . ? C32 C31 C36 C35 0.5(2) . . . . ? C8 C31 C36 C35 178.42(14) . . . . ? C31 C8 C41 C46 -110.48(16) . . . . ? C9 C8 C41 C46 14.72(19) . . . . ? C7 C8 C41 C46 128.60(15) . . . . ? C31 C8 C41 C42 67.78(18) . . . . ? C9 C8 C41 C42 -167.02(13) . . . . ? C7 C8 C41 C42 -53.13(18) . . . . ? C46 C41 C42 C43 0.5(2) . . . . ? C8 C41 C42 C43 -177.86(14) . . . . ? C41 C42 C43 C44 -0.7(2) . . . . ? C42 C43 C44 C45 0.3(2) . . . . ? C43 C44 C45 C46 0.3(2) . . . . ? C44 C45 C46 C41 -0.6(2) . . . . ? C42 C41 C46 C45 0.2(2) . . . . ? C8 C41 C46 C45 178.49(14) . . . . ? N1 C9 C51 C56 28.4(2) . . . . ? C8 C9 C51 C56 -155.47(14) . . . . ? N1 C9 C51 C52 -145.34(15) . . . . ? C8 C9 C51 C52 30.8(2) . . . . ? C56 C51 C52 C53 -0.5(2) . . . . ? C9 C51 C52 C53 173.48(15) . . . . ? C51 C52 C53 C54 0.3(2) . . . . ? C58 N3 C54 C55 2.9(2) . . . . ? C57 N3 C54 C55 161.87(15) . . . . ? C58 N3 C54 C53 -178.40(15) . . . . ? C57 N3 C54 C53 -19.4(2) . . . . ? C52 C53 C54 N3 -177.98(15) . . . . ? C52 C53 C54 C55 0.8(2) . . . . ? N3 C54 C55 C56 176.96(15) . . . . ? C53 C54 C55 C56 -1.8(2) . . . . ? C54 C55 C56 C51 1.7(2) . . . . ? C52 C51 C56 C55 -0.5(2) . . . . ? C9 C51 C56 C55 -174.66(15) . . . . ? _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.320 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.049 #===END