# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Michael Coogan' _publ_contact_author_email COOGANMP@CF.AC.UK _publ_section_title ; Stereostructural Behaviour Of N-N Atropisomers: Two Conglomerate Crystallisations And A Crystallisation-Induced Deracemisation. ; _publ_author_address 'Cardiff University CF10 3AT' _publ_contact_author 'coogan, michael peter' loop_ _publ_author_name 'Michael Coogan' 'Richard J. Arthur' 'Meritxell Casadesus' 'M Francesconi' 'Robert Haigh' ; D.Headspith ; 'Rebecca Laye' # Attachment 'stereostructural_studies_of_N-N_atropisomers.cif' data_C14H14N4O2 _database_code_depnum_ccdc_archive 'CCDC 702071' _audit_creation_method SHELXL-97 _publ_section_abstract ; Structural properties of NN atropisomers are discussed ; _chemical_name_systematic ; 1,2-bis-(2-aminobenzoyl)hydrazine ; _chemical_name_common 1,2-bis-(2-aminobenzoyl)hydrazine _chemical_melting_point 212 _chemical_formula_moiety 'C14 H14 N4 O2' _chemical_formula_sum 'C14 H14 N4 O2' _chemical_formula_weight 270.29 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.1158(3) _cell_length_b 9.9478(4) _cell_length_c 13.7725(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1248.92(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11218 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11134 _diffrn_reflns_av_R_equivalents 0.1509 _diffrn_reflns_av_sigmaI/netI 0.0900 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.44 _reflns_number_total 1643 _reflns_number_gt 1094 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.034(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 1643 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8639(3) 0.0636(3) 0.62669(17) 0.0329(7) Uani 1 1 d . . . N2 N 1.0015(3) 0.2508(3) 0.63664(19) 0.0269(7) Uani 1 1 d . . . C3 C 1.1943(4) 0.0614(4) 0.3422(2) 0.0264(8) Uani 1 1 d . . . C4 C 0.9039(4) 0.1545(4) 0.7855(2) 0.0248(8) Uani 1 1 d . . . C5 C 1.0460(4) 0.2631(4) 0.3296(2) 0.0251(8) Uani 1 1 d . . . H5 H 0.9995 0.3377 0.3596 0.030 Uiso 1 1 calc R . . N6 N 1.0149(4) 0.2488(3) 0.5363(2) 0.0281(7) Uani 1 1 d . . . C7 C 0.9367(4) 0.2736(4) 0.9390(3) 0.0305(9) Uani 1 1 d . . . H7 H 0.9767 0.3468 0.9746 0.037 Uiso 1 1 calc R . . C10 C 1.1814(4) 0.0467(4) 0.2415(2) 0.0313(9) Uani 1 1 d . . . H10 H 1.2265 -0.0279 0.2104 0.038 Uiso 1 1 calc R . . C11 C 0.7973(4) 0.0684(4) 0.9338(2) 0.0313(9) Uani 1 1 d . . . H11 H 0.7414 0.0020 0.9668 0.038 Uiso 1 1 calc R . . C12 C 1.0360(4) 0.2476(4) 0.2302(2) 0.0291(9) Uani 1 1 d . . . H12 H 0.9831 0.3106 0.1920 0.035 Uiso 1 1 calc R . . C14 C 0.9598(4) 0.2630(4) 0.8398(2) 0.0265(9) Uani 1 1 d . . . H14 H 1.0148 0.3308 0.8076 0.032 Uiso 1 1 calc R . . C15 C 1.1227(4) 0.1714(3) 0.3866(2) 0.0244(8) Uani 1 1 d . . . C16 C 0.9213(4) 0.1498(4) 0.6781(2) 0.0250(8) Uani 1 1 d . . . C17 C 0.8211(4) 0.0567(4) 0.8340(2) 0.0245(8) Uani 1 1 d . . . C18 C 0.8546(4) 0.1761(4) 0.9852(2) 0.0324(9) Uani 1 1 d . . . H18 H 0.8372 0.1829 1.0530 0.039 Uiso 1 1 calc R . . C19 C 1.1049(4) 0.1380(4) 0.1869(2) 0.0320(9) Uani 1 1 d . . . H19 H 1.0988 0.1264 0.1186 0.038 Uiso 1 1 calc R . . C20 C 1.1309(4) 0.1873(3) 0.4943(2) 0.0251(8) Uani 1 1 d . . . O2 O 1.2364(3) 0.1502(3) 0.54398(17) 0.0330(7) Uani 1 1 d . . . N4 N 0.7645(4) -0.0573(3) 0.7873(2) 0.0305(8) Uani 1 1 d . . . N3 N 1.2681(4) -0.0350(4) 0.3948(3) 0.0363(9) Uani 1 1 d . . . H1 H 0.936(4) 0.269(4) 0.503(3) 0.024(10) Uiso 1 1 d . . . H4 H 1.296(4) -0.015(4) 0.453(3) 0.035(12) Uiso 1 1 d . . . H6 H 1.070(5) 0.295(4) 0.672(3) 0.047(13) Uiso 1 1 d . . . H8 H 1.325(5) -0.087(5) 0.358(3) 0.048(13) Uiso 1 1 d . . . H2 H 0.688(5) -0.099(4) 0.818(2) 0.031(11) Uiso 1 1 d . . . H3 H 0.761(5) -0.041(4) 0.719(3) 0.044(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0377(16) 0.0338(15) 0.0271(12) -0.0023(11) -0.0047(12) -0.0029(14) N2 0.0265(16) 0.0379(18) 0.0162(15) -0.0020(13) 0.0037(14) -0.0044(18) C3 0.026(2) 0.0261(19) 0.0268(18) -0.0008(15) 0.0038(15) -0.0015(18) C4 0.0230(19) 0.0268(19) 0.0245(18) 0.0010(14) 0.0003(15) 0.0036(17) C5 0.0204(19) 0.0283(19) 0.0267(19) 0.0006(15) 0.0025(14) 0.0009(17) N6 0.0248(16) 0.0401(19) 0.0195(15) -0.0010(13) 0.0025(14) 0.0027(17) C7 0.029(2) 0.036(2) 0.0262(19) -0.0036(16) -0.0052(16) 0.0000(18) C10 0.032(2) 0.031(2) 0.031(2) -0.0038(16) 0.0068(17) -0.0037(18) C11 0.029(2) 0.037(2) 0.028(2) 0.0045(16) 0.0004(17) 0.0044(19) C12 0.027(2) 0.035(2) 0.0253(19) 0.0031(16) 0.0003(15) -0.0032(19) C14 0.0241(19) 0.029(2) 0.0261(19) -0.0014(15) 0.0033(15) -0.0009(18) C15 0.0216(18) 0.0293(19) 0.0224(18) -0.0006(14) 0.0028(15) -0.0031(18) C16 0.0230(18) 0.029(2) 0.0232(18) 0.0030(16) -0.0010(15) 0.0057(18) C17 0.0214(19) 0.0274(19) 0.0248(18) 0.0001(14) 0.0000(15) 0.0055(17) C18 0.035(2) 0.043(2) 0.0187(17) 0.0016(15) 0.0017(17) 0.008(2) C19 0.032(2) 0.043(2) 0.0214(18) 0.0001(17) 0.0005(16) -0.005(2) C20 0.0267(19) 0.0256(19) 0.0229(18) 0.0022(14) 0.0009(16) -0.0047(17) O2 0.0292(14) 0.0439(16) 0.0258(13) 0.0036(11) -0.0032(12) 0.0067(14) N4 0.0323(19) 0.0270(17) 0.0321(19) 0.0022(13) 0.0018(15) -0.0050(16) N3 0.040(2) 0.0338(19) 0.035(2) 0.0021(14) 0.0020(17) 0.0091(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C16 1.229(4) . ? N2 C16 1.367(5) . ? N2 N6 1.387(4) . ? N2 H6 0.91(4) . ? C3 N3 1.377(5) . ? C3 C10 1.400(5) . ? C3 C15 1.414(5) . ? C4 C17 1.402(5) . ? C4 C14 1.409(5) . ? C4 C16 1.489(4) . ? C5 C12 1.381(5) . ? C5 C15 1.392(5) . ? C5 H5 0.9500 . ? N6 C20 1.352(5) . ? N6 H1 0.88(4) . ? C7 C18 1.380(5) . ? C7 C14 1.386(5) . ? C7 H7 0.9500 . ? C10 C19 1.370(5) . ? C10 H10 0.9500 . ? C11 C18 1.386(5) . ? C11 C17 1.396(5) . ? C11 H11 0.9500 . ? C12 C19 1.392(5) . ? C12 H12 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.494(4) . ? C17 N4 1.402(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O2 1.236(4) . ? N4 H2 0.91(4) . ? N4 H3 0.96(4) . ? N3 H4 0.87(4) . ? N3 H8 0.89(5) . ? 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 C16 N2 N6 116.9(3) . . ? C16 N2 H6 120(3) . . ? N6 N2 H6 119(3) . . ? N3 C3 C10 119.3(3) . . ? N3 C3 C15 122.5(3) . . ? C10 C3 C15 118.1(3) . . ? C17 C4 C14 118.3(3) . . ? C17 C4 C16 120.7(3) . . ? C14 C4 C16 120.9(3) . . ? C12 C5 C15 121.3(3) . . ? C12 C5 H5 119.3 . . ? C15 C5 H5 119.3 . . ? C20 N6 N2 120.1(3) . . ? C20 N6 H1 121(2) . . ? N2 N6 H1 117(2) . . ? C18 C7 C14 118.9(3) . . ? C18 C7 H7 120.6 . . ? C14 C7 H7 120.6 . . ? C19 C10 C3 121.2(4) . . ? C19 C10 H10 119.4 . . ? C3 C10 H10 119.4 . . ? C18 C11 C17 120.6(3) . . ? C18 C11 H11 119.7 . . ? C17 C11 H11 119.7 . . ? C5 C12 C19 118.8(3) . . ? C5 C12 H12 120.6 . . ? C19 C12 H12 120.6 . . ? C7 C14 C4 121.8(3) . . ? C7 C14 H14 119.1 . . ? C4 C14 H14 119.1 . . ? C5 C15 C3 119.7(3) . . ? C5 C15 C20 121.1(3) . . ? C3 C15 C20 119.3(3) . . ? O1 C16 N2 120.0(3) . . ? O1 C16 C4 123.3(3) . . ? N2 C16 C4 116.7(3) . . ? C11 C17 N4 117.6(3) . . ? C11 C17 C4 119.7(3) . . ? N4 C17 C4 122.7(3) . . ? C7 C18 C11 120.8(3) . . ? C7 C18 H18 119.6 . . ? C11 C18 H18 119.6 . . ? C10 C19 C12 120.9(3) . . ? C10 C19 H19 119.5 . . ? C12 C19 H19 119.5 . . ? O2 C20 N6 120.5(3) . . ? O2 C20 C15 123.8(3) . . ? N6 C20 C15 115.7(3) . . ? C17 N4 H2 116(2) . . ? C17 N4 H3 109(2) . . ? H2 N4 H3 120(4) . . ? C3 N3 H4 118(3) . . ? C3 N3 H8 113(3) . . ? H4 N3 H8 119(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N2 N6 C20 -92.8(4) . . . . ? N3 C3 C10 C19 177.9(4) . . . . ? C15 C3 C10 C19 1.7(5) . . . . ? C15 C5 C12 C19 -0.2(5) . . . . ? C18 C7 C14 C4 -1.1(5) . . . . ? C17 C4 C14 C7 1.0(5) . . . . ? C16 C4 C14 C7 175.8(3) . . . . ? C12 C5 C15 C3 1.2(5) . . . . ? C12 C5 C15 C20 -178.9(3) . . . . ? N3 C3 C15 C5 -177.9(3) . . . . ? C10 C3 C15 C5 -1.9(5) . . . . ? N3 C3 C15 C20 2.2(5) . . . . ? C10 C3 C15 C20 178.2(3) . . . . ? N6 N2 C16 O1 -0.7(5) . . . . ? N6 N2 C16 C4 -178.4(3) . . . . ? C17 C4 C16 O1 1.1(5) . . . . ? C14 C4 C16 O1 -173.6(3) . . . . ? C17 C4 C16 N2 178.8(3) . . . . ? C14 C4 C16 N2 4.0(5) . . . . ? C18 C11 C17 N4 177.7(3) . . . . ? C18 C11 C17 C4 0.1(5) . . . . ? C14 C4 C17 C11 -0.5(5) . . . . ? C16 C4 C17 C11 -175.4(3) . . . . ? C14 C4 C17 N4 -177.9(3) . . . . ? C16 C4 C17 N4 7.2(5) . . . . ? C14 C7 C18 C11 0.7(6) . . . . ? C17 C11 C18 C7 -0.2(6) . . . . ? C3 C10 C19 C12 -0.8(6) . . . . ? C5 C12 C19 C10 0.0(5) . . . . ? N2 N6 C20 O2 -10.8(5) . . . . ? N2 N6 C20 C15 170.4(3) . . . . ? C5 C15 C20 O2 -149.2(3) . . . . ? C3 C15 C20 O2 30.7(5) . . . . ? C5 C15 C20 N6 29.5(5) . . . . ? C3 C15 C20 N6 -150.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.287 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.067 #===END data_C18H14N4OS _database_code_depnum_ccdc_archive 'CCDC 702072' _audit_creation_method SHELXL-97 _publ_section_abstract ; Structural properties of NN atropisomers are discussed ; _chemical_name_systematic ; 2,2'-Dimethyl-3,3'-biquinazoline-4-thio-4'-one ; _chemical_name_common 2,2'-Dimethyl-3,3'-biquinazoline-4-thio-4'-one _chemical_melting_point 173 _chemical_formula_moiety 'C18 H14 N4 O S' _chemical_formula_sum 'C18 H14 N4 O S' _chemical_formula_weight 334.39 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.054(2) _cell_length_b 10.367(3) _cell_length_c 9.995(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.174(11) _cell_angle_gamma 90.00 _cell_volume 792.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13511 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex2 Kappa ' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15758 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 29.57 _reflns_number_total 4295 _reflns_number_gt 3800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex version 2.1' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_ls_number_reflns 4295 _refine_ls_number_parameters 219 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1437 _refine_ls_wR_factor_gt 0.1373 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 S1 S 0.33939(7) 0.12908(7) 0.25035(6) 0.02937(16) Uani 1 1 d . . . C21 C 0.5473(3) 0.1378(2) 0.2591(2) 0.0202(4) Uani 1 1 d . . . N4 N 0.9033(2) 0.17519(18) 0.2633(2) 0.0211(4) Uani 1 1 d . . . C6 C 0.1198(3) 0.6284(2) 0.0710(2) 0.0240(4) Uani 1 1 d . . . H6 H 0.0334 0.6272 -0.0162 0.029 Uiso 1 1 calc R . . N3 N 0.2507(2) 0.44143(19) 0.00227(19) 0.0226(4) Uani 1 1 d . . . C1 C 0.5071(3) 0.4343(2) 0.2774(2) 0.0196(4) Uani 1 1 d . . . N2 N 0.5001(2) 0.35041(17) 0.16456(18) 0.0194(4) Uani 1 1 d . . . C3 C 0.3709(3) 0.3546(2) 0.0333(2) 0.0207(4) Uani 1 1 d . . . C7 C 0.1200(3) 0.7243(2) 0.1680(3) 0.0275(5) Uani 1 1 d . . . H7 H 0.0344 0.7880 0.1445 0.033 Uiso 1 1 calc R . . C5 C 0.2499(3) 0.5335(2) 0.1045(2) 0.0201(4) Uani 1 1 d . . . C8 C 0.3821(3) 0.2555(2) -0.0732(2) 0.0286(5) Uani 1 1 d . . . H8A H 0.2875 0.2679 -0.1587 0.043 Uiso 1 1 calc R . . H8B H 0.3748 0.1707 -0.0369 0.043 Uiso 1 1 calc R . . H8C H 0.4913 0.2647 -0.0921 0.043 Uiso 1 1 calc R . . O1 O 0.6208(2) 0.41909(16) 0.39415(15) 0.0244(3) Uani 1 1 d . . . C12 C 0.9484(3) -0.1276(2) 0.4590(3) 0.0288(5) Uani 1 1 d . . . H12 H 1.0365 -0.1850 0.5046 0.035 Uiso 1 1 calc R . . C14 C 0.6446(3) -0.0659(2) 0.3930(2) 0.0238(5) Uani 1 1 d . . . H14 H 0.5311 -0.0812 0.3938 0.029 Uiso 1 1 calc R . . C11 C 0.9870(3) -0.0204(2) 0.3916(2) 0.0263(5) Uani 1 1 d . . . H11 H 1.1008 -0.0061 0.3910 0.032 Uiso 1 1 calc R . . C13 C 0.7754(3) -0.1498(2) 0.4586(2) 0.0285(5) Uani 1 1 d . . . H13 H 0.7502 -0.2223 0.5034 0.034 Uiso 1 1 calc R . . C16 C 0.3752(3) 0.6314(2) 0.3379(2) 0.0226(4) Uani 1 1 d . . . H16 H 0.4585 0.6315 0.4265 0.027 Uiso 1 1 calc R . . C17 C 0.2479(3) 0.7266(2) 0.3013(3) 0.0267(5) Uani 1 1 d . . . H17 H 0.2471 0.7919 0.3648 0.032 Uiso 1 1 calc R . . C15 C 0.3769(3) 0.5344(2) 0.2390(2) 0.0202(4) Uani 1 1 d . . . C19 C 0.6819(3) 0.0443(2) 0.3240(2) 0.0194(4) Uani 1 1 d . . . C18 C 0.8544(3) 0.0663(2) 0.3244(2) 0.0203(4) Uani 1 1 d . . . N1 N 0.6102(2) 0.24283(17) 0.20154(19) 0.0188(4) Uani 1 1 d . . . C22 C 0.7848(3) 0.2603(2) 0.2075(2) 0.0193(4) Uani 1 1 d . . . C4 C 0.8335(3) 0.3822(2) 0.1492(3) 0.0266(5) Uani 1 1 d . . . H4A H 0.8279 0.4531 0.2095 0.040 Uiso 1 1 calc R . . H4B H 0.7537 0.3971 0.0567 0.040 Uiso 1 1 calc R . . H4C H 0.9502 0.3748 0.1440 0.040 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 S1 0.0213(3) 0.0322(3) 0.0356(3) 0.0068(3) 0.0103(2) 0.0005(3) C21 0.0197(9) 0.0226(10) 0.0183(9) -0.0018(8) 0.0060(7) -0.0008(9) N4 0.0218(9) 0.0184(8) 0.0256(9) -0.0002(7) 0.0110(7) 0.0007(7) C6 0.0211(9) 0.0239(9) 0.0280(10) 0.0093(10) 0.0092(8) 0.0030(10) N3 0.0230(9) 0.0230(8) 0.0212(9) 0.0004(7) 0.0061(7) 0.0006(8) C1 0.0187(10) 0.0193(9) 0.0224(10) -0.0013(8) 0.0088(8) -0.0019(8) N2 0.0189(8) 0.0175(8) 0.0215(8) 0.0000(7) 0.0058(7) 0.0046(7) C3 0.0225(10) 0.0204(10) 0.0199(10) 0.0000(8) 0.0077(8) 0.0006(8) C7 0.0255(11) 0.0241(11) 0.0371(13) 0.0065(10) 0.0160(10) 0.0076(9) C5 0.0207(10) 0.0186(9) 0.0239(10) 0.0024(8) 0.0111(8) 0.0000(8) C8 0.0330(13) 0.0272(12) 0.0231(11) -0.0036(9) 0.0053(9) 0.0051(10) O1 0.0238(8) 0.0294(8) 0.0192(7) 0.0026(6) 0.0057(6) 0.0117(7) C12 0.0313(13) 0.0283(12) 0.0271(11) 0.0062(10) 0.0096(9) 0.0113(10) C14 0.0262(11) 0.0225(10) 0.0258(11) 0.0023(9) 0.0124(9) -0.0014(9) C11 0.0222(11) 0.0289(12) 0.0286(12) 0.0049(9) 0.0092(9) 0.0063(9) C13 0.0366(13) 0.0229(11) 0.0290(11) 0.0058(9) 0.0144(10) 0.0014(10) C16 0.0236(10) 0.0206(9) 0.0263(10) -0.0015(9) 0.0118(8) -0.0016(10) C17 0.0292(12) 0.0215(10) 0.0344(12) -0.0002(9) 0.0173(10) 0.0029(9) C15 0.0181(10) 0.0191(9) 0.0253(10) 0.0009(8) 0.0097(8) -0.0020(8) C19 0.0213(10) 0.0174(9) 0.0205(9) -0.0002(8) 0.0081(8) -0.0003(8) C18 0.0232(10) 0.0188(9) 0.0207(10) 0.0006(8) 0.0097(8) 0.0025(8) N1 0.0169(8) 0.0171(8) 0.0227(8) 0.0013(7) 0.0068(7) 0.0031(7) C22 0.0171(10) 0.0191(10) 0.0242(10) -0.0010(8) 0.0099(8) -0.0004(8) C4 0.0274(11) 0.0195(10) 0.0364(12) 0.0035(9) 0.0147(10) 0.0007(9) _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 S1 C21 1.652(2) . ? C21 N1 1.398(3) . ? C21 C19 1.448(3) . ? N4 C22 1.292(3) . ? N4 C18 1.397(3) . ? C6 C7 1.389(4) . ? C6 C5 1.400(3) . ? C6 H6 0.9300 . ? N3 C3 1.287(3) . ? N3 C5 1.400(3) . ? C1 O1 1.249(2) . ? C1 N2 1.411(3) . ? C1 C15 1.440(3) . ? N2 C3 1.398(3) . ? N2 N1 1.401(2) . ? C3 C8 1.503(3) . ? C7 C17 1.408(3) . ? C7 H7 0.9300 . ? C5 C15 1.412(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C12 C11 1.384(3) . ? C12 C13 1.411(4) . ? C12 H12 0.9300 . ? C14 C13 1.366(3) . ? C14 C19 1.414(3) . ? C14 H14 0.9300 . ? C11 C18 1.397(3) . ? C11 H11 0.9300 . ? C13 H13 0.9300 . ? C16 C17 1.387(3) . ? C16 C15 1.413(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 C18 1.407(3) . ? N1 C22 1.401(3) . ? C22 C4 1.495(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C21 C19 112.91(18) . . ? N1 C21 S1 120.82(16) . . ? C19 C21 S1 126.27(17) . . ? C22 N4 C18 118.01(19) . . ? C7 C6 C5 119.9(2) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C3 N3 C5 118.37(19) . . ? O1 C1 N2 120.28(19) . . ? O1 C1 C15 126.9(2) . . ? N2 C1 C15 112.78(18) . . ? C3 N2 N1 119.80(17) . . ? C3 N2 C1 124.27(17) . . ? N1 N2 C1 114.55(17) . . ? N3 C3 N2 122.14(19) . . ? N3 C3 C8 120.9(2) . . ? N2 C3 C8 116.88(19) . . ? C6 C7 C17 120.9(2) . . ? C6 C7 H7 119.5 . . ? C17 C7 H7 119.5 . . ? N3 C5 C6 118.5(2) . . ? N3 C5 C15 122.18(19) . . ? C6 C5 C15 119.3(2) . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C12 C13 120.1(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C13 C14 C19 119.9(2) . . ? C13 C14 H14 120.0 . . ? C19 C14 H14 120.0 . . ? C12 C11 C18 119.8(2) . . ? C12 C11 H11 120.1 . . ? C18 C11 H11 120.1 . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C17 C16 C15 119.3(2) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C7 120.0(2) . . ? C16 C17 H17 120.0 . . ? C7 C17 H17 120.0 . . ? C5 C15 C16 120.6(2) . . ? C5 C15 C1 119.97(19) . . ? C16 C15 C1 119.47(19) . . ? C18 C19 C14 119.3(2) . . ? C18 C19 C21 119.54(19) . . ? C14 C19 C21 121.1(2) . . ? C11 C18 N4 116.9(2) . . ? C11 C18 C19 120.2(2) . . ? N4 C18 C19 122.87(19) . . ? C21 N1 N2 116.63(17) . . ? C21 N1 C22 124.81(18) . . ? N2 N1 C22 116.91(17) . . ? N4 C22 N1 121.79(19) . . ? N4 C22 C4 119.9(2) . . ? N1 C22 C4 118.33(19) . . ? C22 C4 H4A 109.5 . . ? C22 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C22 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 N2 C3 175.5(2) . . . . ? C15 C1 N2 C3 -6.2(3) . . . . ? O1 C1 N2 N1 9.0(3) . . . . ? C15 C1 N2 N1 -172.68(17) . . . . ? C5 N3 C3 N2 -0.6(3) . . . . ? C5 N3 C3 C8 -178.1(2) . . . . ? N1 N2 C3 N3 169.6(2) . . . . ? C1 N2 C3 N3 3.7(3) . . . . ? N1 N2 C3 C8 -12.8(3) . . . . ? C1 N2 C3 C8 -178.6(2) . . . . ? C5 C6 C7 C17 -1.1(3) . . . . ? C3 N3 C5 C6 179.8(2) . . . . ? C3 N3 C5 C15 0.6(3) . . . . ? C7 C6 C5 N3 -177.22(19) . . . . ? C7 C6 C5 C15 2.0(3) . . . . ? C13 C12 C11 C18 0.6(4) . . . . ? C19 C14 C13 C12 0.3(4) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C15 C16 C17 C7 1.4(3) . . . . ? C6 C7 C17 C16 -0.6(3) . . . . ? N3 C5 C15 C16 177.92(19) . . . . ? C6 C5 C15 C16 -1.2(3) . . . . ? N3 C5 C15 C1 -3.5(3) . . . . ? C6 C5 C15 C1 177.3(2) . . . . ? C17 C16 C15 C5 -0.4(3) . . . . ? C17 C16 C15 C1 -179.0(2) . . . . ? O1 C1 C15 C5 -176.0(2) . . . . ? N2 C1 C15 C5 5.9(3) . . . . ? O1 C1 C15 C16 2.6(3) . . . . ? N2 C1 C15 C16 -175.55(18) . . . . ? C13 C14 C19 C18 -0.2(3) . . . . ? C13 C14 C19 C21 -177.3(2) . . . . ? N1 C21 C19 C18 0.3(3) . . . . ? S1 C21 C19 C18 -179.24(17) . . . . ? N1 C21 C19 C14 177.35(19) . . . . ? S1 C21 C19 C14 -2.2(3) . . . . ? C12 C11 C18 N4 177.4(2) . . . . ? C12 C11 C18 C19 -0.5(3) . . . . ? C22 N4 C18 C11 -176.2(2) . . . . ? C22 N4 C18 C19 1.7(3) . . . . ? C14 C19 C18 C11 0.3(3) . . . . ? C21 C19 C18 C11 177.4(2) . . . . ? C14 C19 C18 N4 -177.5(2) . . . . ? C21 C19 C18 N4 -0.4(3) . . . . ? C19 C21 N1 N2 -166.42(17) . . . . ? S1 C21 N1 N2 13.2(3) . . . . ? C19 C21 N1 C22 -1.6(3) . . . . ? S1 C21 N1 C22 178.05(16) . . . . ? C3 N2 N1 C21 -84.7(2) . . . . ? C1 N2 N1 C21 82.5(2) . . . . ? C3 N2 N1 C22 109.3(2) . . . . ? C1 N2 N1 C22 -83.6(2) . . . . ? C18 N4 C22 N1 -2.9(3) . . . . ? C18 N4 C22 C4 176.13(19) . . . . ? C21 N1 C22 N4 3.0(3) . . . . ? N2 N1 C22 N4 167.8(2) . . . . ? C21 N1 C22 C4 -176.0(2) . . . . ? N2 N1 C22 C4 -11.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.635 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.073 #===END data_C28H18N4O2 _database_code_depnum_ccdc_archive 'CCDC 702073' _audit_creation_method 'WinGX-Routine XCAD4' _publ_section_abstract ; Structural properties of NN atropisomers are discussed ; _chemical_name_systematic ; 2,2'-Diphenyl-3,3-biquinazoline-4,4-dione ; _chemical_name_common 2,2'-Diphenyl-3,3-biquinazoline-4,4-dione _chemical_melting_point ? _chemical_formula_moiety 'C28 H18 N4 O2' _chemical_formula_sum 'C28 H18 N4 O2' _chemical_formula_weight 442.46 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 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 15.979(3) _cell_length_b 14.653(3) _cell_length_c 18.466(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4323.6(15) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4483 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.7451 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 _diffrn_reflns_number 3899 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3899 _reflns_number_gt 2174 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3899 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1221 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1478 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 0.852 _refine_ls_restrained_S_all 0.852 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.09219(10) 0.85543(11) 0.25956(9) 0.0373(4) Uani 1 1 d . . . O2 O 0.14516(10) 0.64935(12) 0.26261(9) 0.0390(5) Uani 1 1 d . . . N1 N 0.07768(10) 0.75862(12) 0.16348(9) 0.0258(4) Uani 1 1 d . . . N2 N -0.04857(12) 0.73706(12) 0.10108(11) 0.0353(5) Uani 1 1 d . . . N3 N 0.16432(10) 0.74296(12) 0.16572(9) 0.0247(4) Uani 1 1 d . . . N4 N 0.29490(12) 0.76659(13) 0.11051(12) 0.0374(5) Uani 1 1 d . . . C1 C 0.02883(13) 0.71586(15) 0.11054(12) 0.0281(5) Uani 1 1 d . . . C2 C -0.08553(14) 0.79950(16) 0.14836(14) 0.0331(6) Uani 1 1 d . . . C3 C -0.17034(15) 0.82037(17) 0.13883(17) 0.0469(7) Uani 1 1 d . . . H3 H -0.2005 0.7945 0.0995 0.056 Uiso 1 1 calc R . . C4 C -0.20994(16) 0.87826(17) 0.18633(16) 0.0487(7) Uani 1 1 d . . . H4 H -0.2676 0.8918 0.1796 0.058 Uiso 1 1 calc R . . C5 C -0.16737(15) 0.91708(17) 0.24364(16) 0.0432(7) Uani 1 1 d . . . H5 H -0.1956 0.9568 0.2762 0.052 Uiso 1 1 calc R . . C6 C -0.08409(14) 0.89792(16) 0.25323(14) 0.0377(6) Uani 1 1 d . . . H6 H -0.0545 0.9246 0.2925 0.045 Uiso 1 1 calc R . . C7 C -0.04254(13) 0.83935(15) 0.20560(12) 0.0292(5) Uani 1 1 d . . . C8 C 0.04634(14) 0.82067(15) 0.21488(12) 0.0276(5) Uani 1 1 d . . . C9 C 0.06669(14) 0.64508(15) 0.06413(12) 0.0284(5) Uani 1 1 d . . . C10 C 0.05744(17) 0.65155(18) -0.01050(13) 0.0436(7) Uani 1 1 d . . . H10 H 0.0309 0.7035 -0.0310 0.052 Uiso 1 1 calc R . . C11 C 0.08678(17) 0.5826(2) -0.05536(14) 0.0501(7) Uani 1 1 d . . . H11 H 0.0818 0.5884 -0.1064 0.060 Uiso 1 1 calc R . . C12 C 0.12302(16) 0.5060(2) -0.02606(15) 0.0486(7) Uani 1 1 d . . . H12 H 0.1423 0.4585 -0.0568 0.058 Uiso 1 1 calc R . . C13 C 0.13135(15) 0.49822(17) 0.04784(14) 0.0413(6) Uani 1 1 d . . . H13 H 0.1559 0.4450 0.0681 0.050 Uiso 1 1 calc R . . C14 C 0.10427(14) 0.56739(16) 0.09256(13) 0.0325(6) Uani 1 1 d . . . H14 H 0.1114 0.5619 0.1435 0.039 Uiso 1 1 calc R . . C15 C 0.21618(14) 0.78580(15) 0.11478(12) 0.0296(5) Uani 1 1 d . . . C16 C 0.32897(14) 0.70514(15) 0.15975(14) 0.0350(6) Uani 1 1 d . . . C17 C 0.41464(15) 0.68380(18) 0.15412(18) 0.0511(8) Uani 1 1 d . . . H17 H 0.4478 0.7106 0.1171 0.061 Uiso 1 1 calc R . . C18 C 0.45015(16) 0.62363(18) 0.20277(18) 0.0548(8) Uani 1 1 d . . . H18 H 0.5078 0.6087 0.1985 0.066 Uiso 1 1 calc R . . C19 C 0.40352(16) 0.58477(17) 0.25746(17) 0.0468(7) Uani 1 1 d . . . H19 H 0.4290 0.5439 0.2907 0.056 Uiso 1 1 calc R . . C20 C 0.32056(15) 0.60539(16) 0.26358(14) 0.0379(6) Uani 1 1 d . . . H20 H 0.2884 0.5790 0.3015 0.045 Uiso 1 1 calc R . . C21 C 0.28255(13) 0.66492(15) 0.21471(13) 0.0304(6) Uani 1 1 d . . . C22 C 0.19316(13) 0.68331(15) 0.21954(12) 0.0274(5) Uani 1 1 d . . . C23 C 0.17822(14) 0.85087(15) 0.06293(12) 0.0320(6) Uani 1 1 d . . . C24 C 0.18588(18) 0.83221(19) -0.01028(14) 0.0472(7) Uani 1 1 d . . . H24 H 0.2131 0.7779 -0.0255 0.057 Uiso 1 1 calc R . . C25 C 0.1543(2) 0.8918(2) -0.06126(16) 0.0614(9) Uani 1 1 d . . . H25 H 0.1592 0.8781 -0.1114 0.074 Uiso 1 1 calc R . . C26 C 0.11608(19) 0.9706(2) -0.03960(17) 0.0607(9) Uani 1 1 d . . . H26 H 0.0944 1.0116 -0.0748 0.073 Uiso 1 1 calc R . . C27 C 0.10885(18) 0.9909(2) 0.03282(16) 0.0554(8) Uani 1 1 d . . . H27 H 0.0828 1.0461 0.0476 0.066 Uiso 1 1 calc R . . C28 C 0.13939(15) 0.93094(16) 0.08414(13) 0.0373(6) Uani 1 1 d . . . H28 H 0.1337 0.9447 0.1342 0.045 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 O1 0.0264(9) 0.0503(11) 0.0353(9) -0.0116(8) -0.0045(8) 0.0039(8) O2 0.0283(9) 0.0560(12) 0.0328(9) 0.0129(9) 0.0016(8) 0.0038(8) N1 0.0167(10) 0.0334(11) 0.0275(10) -0.0003(9) -0.0021(7) 0.0037(8) N2 0.0284(11) 0.0307(11) 0.0469(13) 0.0009(10) -0.0126(9) 0.0031(9) N3 0.0163(9) 0.0312(10) 0.0265(10) -0.0007(8) 0.0007(7) 0.0022(8) N4 0.0291(11) 0.0310(11) 0.0522(13) -0.0010(10) 0.0125(10) -0.0013(9) C1 0.0278(13) 0.0278(12) 0.0288(12) 0.0029(10) -0.0072(10) -0.0004(10) C2 0.0233(12) 0.0251(12) 0.0508(15) 0.0042(12) -0.0052(11) 0.0023(10) C3 0.0279(14) 0.0369(14) 0.076(2) -0.0021(14) -0.0163(14) 0.0013(11) C4 0.0204(13) 0.0380(15) 0.088(2) 0.0051(16) -0.0014(14) 0.0054(12) C5 0.0287(14) 0.0332(14) 0.0677(19) 0.0019(13) 0.0086(13) 0.0059(12) C6 0.0270(13) 0.0374(15) 0.0488(15) -0.0008(12) 0.0044(11) 0.0046(11) C7 0.0226(12) 0.0286(13) 0.0364(13) 0.0041(10) -0.0016(10) 0.0027(10) C8 0.0242(12) 0.0311(12) 0.0274(12) 0.0003(10) 0.0016(10) 0.0009(10) C9 0.0260(12) 0.0294(12) 0.0297(12) -0.0014(11) -0.0030(10) -0.0024(10) C10 0.0544(17) 0.0457(16) 0.0306(13) 0.0002(12) -0.0094(13) 0.0025(13) C11 0.0581(19) 0.0626(19) 0.0294(14) -0.0066(14) -0.0003(13) -0.0088(15) C12 0.0404(16) 0.0579(18) 0.0475(16) -0.0208(15) 0.0053(13) 0.0021(14) C13 0.0361(14) 0.0373(14) 0.0506(16) -0.0056(13) -0.0012(12) 0.0070(12) C14 0.0301(13) 0.0331(13) 0.0343(13) 0.0011(11) -0.0048(10) -0.0004(11) C15 0.0309(13) 0.0265(12) 0.0316(13) -0.0029(10) 0.0066(10) -0.0004(10) C16 0.0245(13) 0.0249(12) 0.0557(16) -0.0044(12) 0.0022(11) -0.0007(10) C17 0.0232(14) 0.0386(15) 0.092(2) -0.0021(16) 0.0125(14) -0.0034(12) C18 0.0225(14) 0.0390(16) 0.103(2) -0.0170(17) -0.0132(16) 0.0080(12) C19 0.0335(15) 0.0313(14) 0.075(2) -0.0091(14) -0.0184(14) 0.0052(12) C20 0.0315(14) 0.0323(14) 0.0498(16) -0.0026(12) -0.0118(12) 0.0018(11) C21 0.0216(12) 0.0289(13) 0.0406(14) -0.0068(11) -0.0064(10) -0.0009(10) C22 0.0247(12) 0.0327(13) 0.0249(12) -0.0021(10) -0.0022(10) 0.0016(10) C23 0.0334(14) 0.0335(13) 0.0289(12) -0.0019(11) 0.0025(11) -0.0073(11) C24 0.0598(18) 0.0503(17) 0.0316(14) -0.0062(13) 0.0115(13) -0.0039(14) C25 0.073(2) 0.083(2) 0.0280(15) 0.0035(16) 0.0041(15) -0.0163(19) C26 0.058(2) 0.077(2) 0.0468(18) 0.0302(17) -0.0036(15) -0.0056(17) C27 0.067(2) 0.0447(16) 0.0543(18) 0.0132(15) -0.0018(15) 0.0095(15) C28 0.0433(15) 0.0359(14) 0.0327(13) 0.0011(12) 0.0021(11) 0.0031(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.215(3) . ? O2 C22 1.212(3) . ? N1 C1 1.399(3) . ? N1 N3 1.404(2) . ? N1 C8 1.407(3) . ? N2 C1 1.287(3) . ? N2 C2 1.396(3) . ? N3 C22 1.401(3) . ? N3 C15 1.402(3) . ? N4 C15 1.291(3) . ? N4 C16 1.391(3) . ? C1 C9 1.475(3) . ? C2 C7 1.389(3) . ? C2 C3 1.400(3) . ? C3 C4 1.375(4) . ? C3 H3 0.9500 . ? C4 C5 1.381(4) . ? C4 H4 0.9500 . ? C5 C6 1.372(3) . ? C5 H5 0.9500 . ? C6 C7 1.397(3) . ? C6 H6 0.9500 . ? C7 C8 1.457(3) . ? C9 C10 1.389(3) . ? C9 C14 1.390(3) . ? C10 C11 1.388(4) . ? C10 H10 0.9500 . ? C11 C12 1.374(4) . ? C11 H11 0.9500 . ? C12 C13 1.376(4) . ? C12 H12 0.9500 . ? C13 C14 1.377(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C23 1.481(3) . ? C16 C21 1.388(3) . ? C16 C17 1.408(3) . ? C17 C18 1.381(4) . ? C17 H17 0.9500 . ? C18 C19 1.378(4) . ? C18 H18 0.9500 . ? C19 C20 1.364(3) . ? C19 H19 0.9500 . ? C20 C21 1.394(3) . ? C20 H20 0.9500 . ? C21 C22 1.456(3) . ? C23 C28 1.384(3) . ? C23 C24 1.385(3) . ? C24 C25 1.380(4) . ? C24 H24 0.9500 . ? C25 C26 1.366(4) . ? C25 H25 0.9500 . ? C26 C27 1.375(4) . ? C26 H26 0.9500 . ? C27 C28 1.381(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N3 119.85(17) . . ? C1 N1 C8 124.22(18) . . ? N3 N1 C8 115.89(17) . . ? C1 N2 C2 118.7(2) . . ? C22 N3 C15 124.10(18) . . ? C22 N3 N1 116.56(17) . . ? C15 N3 N1 119.33(17) . . ? C15 N4 C16 118.9(2) . . ? N2 C1 N1 121.5(2) . . ? N2 C1 C9 119.0(2) . . ? N1 C1 C9 119.47(19) . . ? C7 C2 N2 122.8(2) . . ? C7 C2 C3 118.8(2) . . ? N2 C2 C3 118.3(2) . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 119.5(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 120.4(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 120.2(2) . . ? C2 C7 C8 119.5(2) . . ? C6 C7 C8 120.3(2) . . ? O1 C8 N1 121.0(2) . . ? O1 C8 C7 126.1(2) . . ? N1 C8 C7 112.91(19) . . ? C10 C9 C14 118.5(2) . . ? C10 C9 C1 119.0(2) . . ? C14 C9 C1 122.2(2) . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.1(2) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.9(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 120.8(2) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? N4 C15 N3 121.3(2) . . ? N4 C15 C23 120.0(2) . . ? N3 C15 C23 118.68(19) . . ? C21 C16 N4 122.9(2) . . ? C21 C16 C17 118.6(2) . . ? N4 C16 C17 118.4(2) . . ? C18 C17 C16 119.6(3) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 121.2(2) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C20 C19 C18 119.6(3) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.5(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C16 C21 C20 120.4(2) . . ? C16 C21 C22 119.4(2) . . ? C20 C21 C22 120.2(2) . . ? O2 C22 N3 120.9(2) . . ? O2 C22 C21 125.8(2) . . ? N3 C22 C21 113.2(2) . . ? C28 C23 C24 118.9(2) . . ? C28 C23 C15 123.1(2) . . ? C24 C23 C15 117.9(2) . . ? C25 C24 C23 120.6(3) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C26 C25 C24 119.9(3) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.3(3) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C26 C27 C28 120.0(3) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C27 C28 C23 120.2(2) . . ? C27 C28 H28 119.9 . . ? C23 C28 H28 119.9 . . ? 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 C1 N1 N3 C22 -103.2(2) . . . . ? C8 N1 N3 C22 79.0(2) . . . . ? C1 N1 N3 C15 76.0(2) . . . . ? C8 N1 N3 C15 -101.8(2) . . . . ? C2 N2 C1 N1 -4.6(3) . . . . ? C2 N2 C1 C9 175.7(2) . . . . ? N3 N1 C1 N2 -171.3(2) . . . . ? C8 N1 C1 N2 6.3(3) . . . . ? N3 N1 C1 C9 8.5(3) . . . . ? C8 N1 C1 C9 -173.93(19) . . . . ? C1 N2 C2 C7 -0.5(3) . . . . ? C1 N2 C2 C3 -178.4(2) . . . . ? C7 C2 C3 C4 -1.0(4) . . . . ? N2 C2 C3 C4 177.0(2) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? N2 C2 C7 C6 -176.8(2) . . . . ? C3 C2 C7 C6 1.0(4) . . . . ? N2 C2 C7 C8 4.1(3) . . . . ? C3 C2 C7 C8 -178.0(2) . . . . ? C5 C6 C7 C2 -0.5(4) . . . . ? C5 C6 C7 C8 178.6(2) . . . . ? C1 N1 C8 O1 179.9(2) . . . . ? N3 N1 C8 O1 -2.4(3) . . . . ? C1 N1 C8 C7 -2.5(3) . . . . ? N3 N1 C8 C7 175.22(18) . . . . ? C2 C7 C8 O1 175.0(2) . . . . ? C6 C7 C8 O1 -4.1(4) . . . . ? C2 C7 C8 N1 -2.5(3) . . . . ? C6 C7 C8 N1 178.5(2) . . . . ? N2 C1 C9 C10 50.3(3) . . . . ? N1 C1 C9 C10 -129.4(2) . . . . ? N2 C1 C9 C14 -123.2(2) . . . . ? N1 C1 C9 C14 57.0(3) . . . . ? C14 C9 C10 C11 -1.3(4) . . . . ? C1 C9 C10 C11 -175.1(2) . . . . ? C9 C10 C11 C12 2.0(4) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C11 C12 C13 C14 -0.7(4) . . . . ? C12 C13 C14 C9 1.3(4) . . . . ? C10 C9 C14 C13 -0.3(4) . . . . ? C1 C9 C14 C13 173.3(2) . . . . ? C16 N4 C15 N3 -2.9(3) . . . . ? C16 N4 C15 C23 -179.9(2) . . . . ? C22 N3 C15 N4 5.9(3) . . . . ? N1 N3 C15 N4 -173.3(2) . . . . ? C22 N3 C15 C23 -177.08(19) . . . . ? N1 N3 C15 C23 3.7(3) . . . . ? C15 N4 C16 C21 -1.6(3) . . . . ? C15 N4 C16 C17 179.3(2) . . . . ? C21 C16 C17 C18 0.2(4) . . . . ? N4 C16 C17 C18 179.4(2) . . . . ? C16 C17 C18 C19 -0.8(4) . . . . ? C17 C18 C19 C20 0.5(4) . . . . ? C18 C19 C20 C21 0.4(4) . . . . ? N4 C16 C21 C20 -178.5(2) . . . . ? C17 C16 C21 C20 0.6(3) . . . . ? N4 C16 C21 C22 3.4(3) . . . . ? C17 C16 C21 C22 -177.5(2) . . . . ? C19 C20 C21 C16 -1.0(3) . . . . ? C19 C20 C21 C22 177.1(2) . . . . ? C15 N3 C22 O2 179.0(2) . . . . ? N1 N3 C22 O2 -1.8(3) . . . . ? C15 N3 C22 C21 -3.8(3) . . . . ? N1 N3 C22 C21 175.36(18) . . . . ? C16 C21 C22 O2 176.4(2) . . . . ? C20 C21 C22 O2 -1.8(4) . . . . ? C16 C21 C22 N3 -0.6(3) . . . . ? C20 C21 C22 N3 -178.8(2) . . . . ? N4 C15 C23 C28 -120.3(3) . . . . ? N3 C15 C23 C28 62.6(3) . . . . ? N4 C15 C23 C24 56.5(3) . . . . ? N3 C15 C23 C24 -120.6(2) . . . . ? C28 C23 C24 C25 -0.9(4) . . . . ? C15 C23 C24 C25 -177.8(2) . . . . ? C23 C24 C25 C26 0.8(4) . . . . ? C24 C25 C26 C27 0.0(5) . . . . ? C25 C26 C27 C28 -0.8(5) . . . . ? C26 C27 C28 C23 0.8(4) . . . . ? C24 C23 C28 C27 0.1(4) . . . . ? C15 C23 C28 C27 176.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.172 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.038 #===END data_C34H28N2O8 _database_code_depnum_ccdc_archive 'CCDC 702074' _audit_creation_method SHELXL-97 _publ_section_abstract ; Structural properties of NN atropisomers are discussed ; _chemical_name_systematic ; (S,S)-1,2-bis- (2-benzoyloxypropanoyl)-1,2-dibenzoylhydrazine ; _chemical_name_common (S,S)-1,2-bis-(2-benzoyloxypropanoyl)-1,2-dibenzoylhydrazine _chemical_melting_point 173 _chemical_formula_moiety 'C34 H28 N2 O8' _chemical_formula_sum 'C34 H28 N2 O8' _chemical_formula_weight 592.58 _chemical_absolute_configuration syn 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.362(2) _cell_length_b 10.943(2) _cell_length_c 25.892(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2935.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3115 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.7224 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 _diffrn_reflns_number 3021 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.32 _reflns_number_total 3021 _reflns_number_gt 2241 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0895P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(19) _refine_ls_number_reflns 3021 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0774(3) 0.5372(3) -0.08707(11) 0.0318(8) Uani 1 1 d . . . O2 O 0.0568(3) 0.5063(3) 0.01341(11) 0.0255(7) Uani 1 1 d . . . O3 O 0.2713(3) 0.5332(3) 0.01033(15) 0.0458(9) Uani 1 1 d . . . O4 O 0.0990(3) 0.8705(3) -0.02028(11) 0.0290(7) Uani 1 1 d . . . O5 O -0.1562(3) 0.6933(3) -0.12491(11) 0.0325(8) Uani 1 1 d . . . O6 O -0.2221(3) 0.6463(3) -0.22522(11) 0.0303(7) Uani 1 1 d . . . O7 O -0.1937(3) 0.8489(3) -0.23237(12) 0.0357(8) Uani 1 1 d . . . O8 O 0.1429(3) 0.7699(4) -0.22085(11) 0.0444(9) Uani 1 1 d . . . N1 N 0.0711(3) 0.7439(3) -0.08850(12) 0.0215(7) Uani 1 1 d . . . N2 N 0.0551(3) 0.7309(3) -0.14231(12) 0.0217(8) Uani 1 1 d . . . C1 C 0.0679(4) 0.6298(4) -0.06225(16) 0.0239(9) Uani 1 1 d . . . C2 C 0.0399(4) 0.6297(4) -0.00451(15) 0.0219(9) Uani 1 1 d . . . H2 H 0.0984 0.6873 0.0143 0.026 Uiso 1 1 calc R . . C3 C -0.1005(4) 0.6619(4) 0.00450(16) 0.0270(10) Uani 1 1 d . . . H3A H -0.1153 0.7474 -0.0050 0.041 Uiso 1 1 calc R . . H3B H -0.1217 0.6501 0.0410 0.041 Uiso 1 1 calc R . . H3C H -0.1553 0.6089 -0.0167 0.041 Uiso 1 1 calc R . . C4 C 0.1800(4) 0.4684(4) 0.01886(16) 0.0260(10) Uani 1 1 d . . . C5 C 0.1877(4) 0.3384(4) 0.03521(16) 0.0266(10) Uani 1 1 d . . . C6 C 0.0785(4) 0.2645(4) 0.03592(16) 0.0303(10) Uani 1 1 d . . . H6 H -0.0033 0.2976 0.0270 0.036 Uiso 1 1 calc R . . C7 C 0.0892(5) 0.1419(4) 0.04967(17) 0.0344(11) Uani 1 1 d . . . H7 H 0.0149 0.0912 0.0501 0.041 Uiso 1 1 calc R . . C8 C 0.2085(5) 0.0942(4) 0.06278(17) 0.0340(12) Uani 1 1 d . . . H8 H 0.2159 0.0105 0.0721 0.041 Uiso 1 1 calc R . . C9 C 0.3169(5) 0.1680(4) 0.06235(17) 0.0326(11) Uani 1 1 d . . . H9 H 0.3985 0.1355 0.0718 0.039 Uiso 1 1 calc R . . C10 C 0.3060(5) 0.2901(4) 0.04797(16) 0.0289(10) Uani 1 1 d . . . H10 H 0.3808 0.3403 0.0470 0.035 Uiso 1 1 calc R . . C11 C 0.0770(4) 0.8618(4) -0.06604(15) 0.0231(9) Uani 1 1 d . . . C12 C 0.0675(4) 0.9722(4) -0.09924(16) 0.0253(9) Uani 1 1 d . . . C13 C -0.0302(5) 0.9899(4) -0.13637(16) 0.0309(10) Uani 1 1 d . . . H13 H -0.0915 0.9275 -0.1433 0.037 Uiso 1 1 calc R . . C14 C -0.0350(6) 1.1004(5) -0.16265(17) 0.0414(13) Uani 1 1 d . . . H14 H -0.1002 1.1136 -0.1878 0.050 Uiso 1 1 calc R . . C15 C 0.0539(6) 1.1915(4) -0.15261(19) 0.0464(14) Uani 1 1 d . . . H15 H 0.0504 1.2657 -0.1716 0.056 Uiso 1 1 calc R . . C16 C 0.1472(6) 1.1759(4) -0.1155(2) 0.0477(14) Uani 1 1 d . . . H16 H 0.2063 1.2399 -0.1081 0.057 Uiso 1 1 calc R . . C17 C 0.1548(5) 1.0658(4) -0.08866(18) 0.0339(11) Uani 1 1 d . . . H17 H 0.2195 1.0545 -0.0631 0.041 Uiso 1 1 calc R . . C18 C -0.0720(4) 0.6927(4) -0.15671(16) 0.0240(9) Uani 1 1 d . . . C19 C -0.0887(4) 0.6375(4) -0.20991(16) 0.0269(10) Uani 1 1 d . . . H19 H -0.0321 0.6802 -0.2355 0.032 Uiso 1 1 calc R . . C20 C -0.0550(5) 0.5030(5) -0.2072(2) 0.0420(13) Uani 1 1 d . . . H20A H -0.1101 0.4628 -0.1815 0.063 Uiso 1 1 calc R . . H20B H 0.0357 0.4938 -0.1972 0.063 Uiso 1 1 calc R . . H20C H -0.0689 0.4654 -0.2411 0.063 Uiso 1 1 calc R . . C21 C -0.2602(4) 0.7596(4) -0.23913(15) 0.0252(9) Uani 1 1 d . . . C22 C -0.3900(4) 0.7605(4) -0.26419(14) 0.0268(10) Uani 1 1 d . . . C23 C -0.4260(5) 0.8654(4) -0.29049(16) 0.0340(11) Uani 1 1 d . . . H23 H -0.3695 0.9336 -0.2924 0.041 Uiso 1 1 calc R . . C24 C -0.5473(5) 0.8688(4) -0.31420(17) 0.0373(11) Uani 1 1 d . . . H24 H -0.5739 0.9401 -0.3322 0.045 Uiso 1 1 calc R . . C25 C -0.6276(5) 0.7699(5) -0.31165(17) 0.0366(12) Uani 1 1 d . . . H25 H -0.7092 0.7728 -0.3283 0.044 Uiso 1 1 calc R . . C26 C -0.5916(5) 0.6657(4) -0.28517(17) 0.0332(11) Uani 1 1 d . . . H26 H -0.6489 0.5982 -0.2829 0.040 Uiso 1 1 calc R . . C27 C -0.4716(4) 0.6605(4) -0.26195(15) 0.0292(10) Uani 1 1 d . . . H27 H -0.4451 0.5884 -0.2445 0.035 Uiso 1 1 calc R . . C28 C 0.1605(4) 0.7547(4) -0.17508(15) 0.0270(9) Uani 1 1 d . . . C29 C 0.2924(4) 0.7643(4) -0.15223(15) 0.0245(9) Uani 1 1 d . . . C30 C 0.3619(4) 0.8681(5) -0.16378(16) 0.0331(11) Uani 1 1 d . . . H30 H 0.3225 0.9326 -0.1826 0.040 Uiso 1 1 calc R . . C31 C 0.4886(5) 0.8786(5) -0.14809(17) 0.0399(12) Uani 1 1 d . . . H31 H 0.5355 0.9516 -0.1548 0.048 Uiso 1 1 calc R . . C32 C 0.5474(4) 0.7822(5) -0.12244(18) 0.0420(13) Uani 1 1 d . . . H32 H 0.6353 0.7881 -0.1123 0.050 Uiso 1 1 calc R . . C33 C 0.4784(5) 0.6785(5) -0.11179(18) 0.0398(13) Uani 1 1 d . . . H33 H 0.5193 0.6126 -0.0944 0.048 Uiso 1 1 calc R . . C34 C 0.3484(5) 0.6680(4) -0.12608(16) 0.0316(11) Uani 1 1 d . . . H34 H 0.3002 0.5966 -0.1180 0.038 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 O1 0.043(2) 0.0238(16) 0.0290(16) 0.0005(13) 0.0015(15) -0.0002(15) O2 0.0250(15) 0.0239(14) 0.0276(15) 0.0073(12) 0.0007(13) -0.0009(13) O3 0.0271(19) 0.0308(18) 0.079(3) 0.0180(18) -0.0077(18) -0.0037(16) O4 0.0354(17) 0.0276(16) 0.0240(15) 0.0015(13) -0.0068(13) -0.0007(14) O5 0.0233(16) 0.044(2) 0.0302(16) -0.0010(14) -0.0003(14) 0.0013(15) O6 0.0258(16) 0.0309(16) 0.0342(16) -0.0003(14) -0.0088(14) 0.0017(15) O7 0.0327(18) 0.0314(17) 0.0430(18) -0.0022(15) -0.0086(15) -0.0055(16) O8 0.0324(18) 0.076(3) 0.0242(16) 0.0143(18) -0.0015(14) -0.0109(19) N1 0.0241(18) 0.0215(16) 0.0190(16) 0.0038(14) -0.0016(14) 0.0031(17) N2 0.0192(17) 0.0290(19) 0.0169(16) 0.0005(14) -0.0012(14) -0.0021(16) C1 0.018(2) 0.025(2) 0.029(2) 0.0011(19) 0.0003(18) 0.004(2) C2 0.022(2) 0.019(2) 0.024(2) 0.0046(16) -0.0035(17) -0.0003(18) C3 0.025(2) 0.030(2) 0.027(2) -0.0014(19) 0.0038(18) 0.0030(19) C4 0.019(2) 0.029(2) 0.030(2) 0.0073(19) -0.0021(18) 0.002(2) C5 0.029(2) 0.026(2) 0.025(2) 0.0006(18) -0.0056(18) 0.002(2) C6 0.028(2) 0.029(2) 0.034(2) 0.0049(19) -0.006(2) 0.001(2) C7 0.038(3) 0.026(2) 0.039(3) 0.005(2) -0.001(2) -0.008(2) C8 0.046(3) 0.026(2) 0.030(2) 0.0023(19) 0.010(2) 0.010(2) C9 0.035(3) 0.033(2) 0.030(2) 0.000(2) -0.002(2) 0.008(2) C10 0.027(2) 0.029(2) 0.031(2) -0.0001(19) -0.0005(19) -0.002(2) C11 0.017(2) 0.025(2) 0.027(2) -0.0002(18) -0.0018(18) 0.0002(19) C12 0.027(2) 0.023(2) 0.026(2) 0.0009(17) 0.0016(19) 0.0005(19) C13 0.036(3) 0.027(2) 0.029(2) 0.0017(18) -0.002(2) 0.007(2) C14 0.059(3) 0.039(3) 0.026(2) 0.007(2) 0.005(2) 0.021(3) C15 0.068(4) 0.029(3) 0.042(3) 0.013(2) 0.011(3) 0.012(3) C16 0.062(4) 0.027(3) 0.054(3) 0.006(2) 0.011(3) -0.007(3) C17 0.037(3) 0.028(2) 0.037(3) 0.003(2) 0.001(2) -0.002(2) C18 0.020(2) 0.023(2) 0.028(2) 0.0020(18) -0.0019(19) 0.0051(18) C19 0.019(2) 0.033(2) 0.029(2) -0.0023(19) -0.0061(17) 0.002(2) C20 0.035(3) 0.039(3) 0.052(3) -0.012(2) -0.012(2) 0.006(2) C21 0.024(2) 0.026(2) 0.025(2) 0.0005(19) -0.0018(17) 0.000(2) C22 0.035(2) 0.028(2) 0.0172(18) -0.0024(18) -0.0023(18) 0.004(2) C23 0.041(3) 0.034(2) 0.027(2) 0.000(2) -0.007(2) 0.004(2) C24 0.049(3) 0.030(2) 0.033(2) 0.004(2) -0.011(2) 0.006(3) C25 0.031(3) 0.047(3) 0.031(2) -0.004(2) -0.012(2) 0.008(2) C26 0.032(3) 0.032(2) 0.035(2) 0.001(2) -0.002(2) -0.001(2) C27 0.029(2) 0.031(2) 0.028(2) -0.0011(19) -0.0057(19) 0.002(2) C28 0.026(2) 0.028(2) 0.027(2) 0.004(2) 0.0015(18) 0.001(2) C29 0.021(2) 0.033(2) 0.0200(19) 0.0006(19) 0.0006(17) 0.003(2) C30 0.026(2) 0.044(3) 0.030(2) 0.004(2) 0.0046(19) 0.000(2) C31 0.030(2) 0.055(3) 0.034(2) 0.001(2) 0.008(2) -0.013(3) C32 0.017(2) 0.076(4) 0.033(2) -0.009(3) 0.001(2) 0.009(3) C33 0.032(3) 0.052(3) 0.036(3) -0.001(2) -0.005(2) 0.022(3) C34 0.033(2) 0.033(3) 0.029(2) -0.002(2) -0.003(2) 0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.204(5) . ? O2 C4 1.349(5) . ? O2 C2 1.439(5) . ? O3 C4 1.203(5) . ? O4 C11 1.210(5) . ? O5 C18 1.200(5) . ? O6 C21 1.350(5) . ? O6 C19 1.441(5) . ? O7 C21 1.209(5) . ? O8 C28 1.210(5) . ? N1 N2 1.410(4) . ? N1 C11 1.417(5) . ? N1 C1 1.422(5) . ? N2 C28 1.408(5) . ? N2 C18 1.431(5) . ? C1 C2 1.523(6) . ? C2 C3 1.514(6) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.486(6) . ? C5 C10 1.375(6) . ? C5 C6 1.391(6) . ? C6 C7 1.392(6) . ? C6 H6 0.9500 . ? C7 C8 1.383(7) . ? C7 H7 0.9500 . ? C8 C9 1.384(7) . ? C8 H8 0.9500 . ? C9 C10 1.391(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.486(6) . ? C12 C17 1.393(6) . ? C12 C13 1.410(6) . ? C13 C14 1.388(6) . ? C13 H13 0.9500 . ? C14 C15 1.382(8) . ? C14 H14 0.9500 . ? C15 C16 1.375(8) . ? C15 H15 0.9500 . ? C16 C17 1.393(6) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.514(6) . ? C19 C20 1.514(7) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.494(6) . ? C22 C27 1.383(6) . ? C22 C23 1.386(6) . ? C23 C24 1.399(7) . ? C23 H23 0.9500 . ? C24 C25 1.367(7) . ? C24 H24 0.9500 . ? C25 C26 1.381(7) . ? C25 H25 0.9500 . ? C26 C27 1.383(6) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.493(6) . ? C29 C30 1.378(6) . ? C29 C34 1.380(6) . ? C30 C31 1.379(7) . ? C30 H30 0.9500 . ? C31 C32 1.388(8) . ? C31 H31 0.9500 . ? C32 C33 1.369(7) . ? C32 H32 0.9500 . ? C33 C34 1.402(7) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C2 115.9(3) . . ? C21 O6 C19 114.5(3) . . ? N2 N1 C11 120.1(3) . . ? N2 N1 C1 112.4(3) . . ? C11 N1 C1 127.2(3) . . ? C28 N2 N1 119.0(3) . . ? C28 N2 C18 127.7(3) . . ? N1 N2 C18 113.3(3) . . ? O1 C1 N1 118.8(3) . . ? O1 C1 C2 122.6(4) . . ? N1 C1 C2 118.3(3) . . ? O2 C2 C3 106.6(3) . . ? O2 C2 C1 107.1(3) . . ? C3 C2 C1 109.5(3) . . ? O2 C2 H2 111.1 . . ? C3 C2 H2 111.1 . . ? C1 C2 H2 111.1 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O3 C4 O2 123.0(4) . . ? O3 C4 C5 125.0(4) . . ? O2 C4 C5 112.0(4) . . ? C10 C5 C6 119.9(4) . . ? C10 C5 C4 119.0(4) . . ? C6 C5 C4 121.1(4) . . ? C5 C6 C7 119.9(4) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 119.9(5) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.2(4) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 119.8(5) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C5 C10 C9 120.4(5) . . ? C5 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? O4 C11 N1 118.8(4) . . ? O4 C11 C12 121.0(4) . . ? N1 C11 C12 120.0(3) . . ? C17 C12 C13 119.9(4) . . ? C17 C12 C11 116.2(4) . . ? C13 C12 C11 123.6(4) . . ? C14 C13 C12 118.7(5) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C15 C14 C13 120.8(5) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C14 120.7(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 119.7(5) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 120.1(5) . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? O5 C18 N2 119.2(4) . . ? O5 C18 C19 122.9(4) . . ? N2 C18 C19 117.3(4) . . ? O6 C19 C18 109.5(3) . . ? O6 C19 C20 107.4(4) . . ? C18 C19 C20 108.6(4) . . ? O6 C19 H19 110.4 . . ? C18 C19 H19 110.4 . . ? C20 C19 H19 110.4 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O7 C21 O6 122.6(4) . . ? O7 C21 C22 124.8(4) . . ? O6 C21 C22 112.7(4) . . ? C27 C22 C23 120.7(4) . . ? C27 C22 C21 121.8(4) . . ? C23 C22 C21 117.5(4) . . ? C22 C23 C24 118.7(5) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? C25 C24 C23 120.3(4) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 120.9(4) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C27 119.5(5) . . ? C25 C26 H26 120.3 . . ? C27 C26 H26 120.3 . . ? C26 C27 C22 119.9(4) . . ? C26 C27 H27 120.0 . . ? C22 C27 H27 120.0 . . ? O8 C28 N2 119.9(4) . . ? O8 C28 C29 121.1(4) . . ? N2 C28 C29 119.0(3) . . ? C30 C29 C34 121.1(4) . . ? C30 C29 C28 116.7(4) . . ? C34 C29 C28 121.7(4) . . ? C29 C30 C31 120.2(5) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C30 C31 C32 119.7(5) . . ? C30 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? C33 C32 C31 119.8(4) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C32 C33 C34 121.1(5) . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C29 C34 C33 118.1(5) . . ? C29 C34 H34 121.0 . . ? C33 C34 H34 121.0 . . ? 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 C11 N1 N2 C28 74.8(5) . . . . ? C1 N1 N2 C28 -110.5(4) . . . . ? C11 N1 N2 C18 -105.7(4) . . . . ? C1 N1 N2 C18 69.0(4) . . . . ? N2 N1 C1 O1 14.0(6) . . . . ? C11 N1 C1 O1 -171.8(4) . . . . ? N2 N1 C1 C2 -160.3(3) . . . . ? C11 N1 C1 C2 13.9(6) . . . . ? C4 O2 C2 C3 -166.7(3) . . . . ? C4 O2 C2 C1 76.1(4) . . . . ? O1 C1 C2 O2 12.4(6) . . . . ? N1 C1 C2 O2 -173.5(3) . . . . ? O1 C1 C2 C3 -102.8(5) . . . . ? N1 C1 C2 C3 71.3(5) . . . . ? C2 O2 C4 O3 1.3(6) . . . . ? C2 O2 C4 C5 -177.4(3) . . . . ? O3 C4 C5 C10 8.5(7) . . . . ? O2 C4 C5 C10 -172.9(4) . . . . ? O3 C4 C5 C6 -169.1(5) . . . . ? O2 C4 C5 C6 9.5(6) . . . . ? C10 C5 C6 C7 0.2(7) . . . . ? C4 C5 C6 C7 177.8(4) . . . . ? C5 C6 C7 C8 0.2(7) . . . . ? C6 C7 C8 C9 0.1(7) . . . . ? C7 C8 C9 C10 -0.9(7) . . . . ? C6 C5 C10 C9 -1.0(6) . . . . ? C4 C5 C10 C9 -178.6(4) . . . . ? C8 C9 C10 C5 1.3(7) . . . . ? N2 N1 C11 O4 -175.4(4) . . . . ? C1 N1 C11 O4 10.8(6) . . . . ? N2 N1 C11 C12 -0.6(6) . . . . ? C1 N1 C11 C12 -174.4(4) . . . . ? O4 C11 C12 C17 38.8(6) . . . . ? N1 C11 C12 C17 -135.9(4) . . . . ? O4 C11 C12 C13 -135.2(5) . . . . ? N1 C11 C12 C13 50.1(6) . . . . ? C17 C12 C13 C14 1.6(6) . . . . ? C11 C12 C13 C14 175.4(4) . . . . ? C12 C13 C14 C15 -0.2(7) . . . . ? C13 C14 C15 C16 -1.6(8) . . . . ? C14 C15 C16 C17 1.9(8) . . . . ? C15 C16 C17 C12 -0.4(8) . . . . ? C13 C12 C17 C16 -1.3(7) . . . . ? C11 C12 C17 C16 -175.6(4) . . . . ? C28 N2 C18 O5 -169.3(4) . . . . ? N1 N2 C18 O5 11.3(5) . . . . ? C28 N2 C18 C19 18.6(6) . . . . ? N1 N2 C18 C19 -160.9(4) . . . . ? C21 O6 C19 C18 74.6(4) . . . . ? C21 O6 C19 C20 -167.7(4) . . . . ? O5 C18 C19 O6 29.3(6) . . . . ? N2 C18 C19 O6 -158.9(3) . . . . ? O5 C18 C19 C20 -87.7(5) . . . . ? N2 C18 C19 C20 84.1(5) . . . . ? C19 O6 C21 O7 -10.0(6) . . . . ? C19 O6 C21 C22 168.9(3) . . . . ? O7 C21 C22 C27 -167.3(4) . . . . ? O6 C21 C22 C27 13.8(5) . . . . ? O7 C21 C22 C23 13.3(6) . . . . ? O6 C21 C22 C23 -165.5(4) . . . . ? C27 C22 C23 C24 0.8(6) . . . . ? C21 C22 C23 C24 -179.8(4) . . . . ? C22 C23 C24 C25 -0.5(7) . . . . ? C23 C24 C25 C26 0.9(7) . . . . ? C24 C25 C26 C27 -1.5(7) . . . . ? C25 C26 C27 C22 1.7(6) . . . . ? C23 C22 C27 C26 -1.4(6) . . . . ? C21 C22 C27 C26 179.2(4) . . . . ? N1 N2 C28 O8 -164.2(4) . . . . ? C18 N2 C28 O8 16.3(7) . . . . ? N1 N2 C28 C29 14.1(6) . . . . ? C18 N2 C28 C29 -165.3(4) . . . . ? O8 C28 C29 C30 51.2(6) . . . . ? N2 C28 C29 C30 -127.1(4) . . . . ? O8 C28 C29 C34 -121.1(5) . . . . ? N2 C28 C29 C34 60.6(6) . . . . ? C34 C29 C30 C31 -1.7(6) . . . . ? C28 C29 C30 C31 -174.1(4) . . . . ? C29 C30 C31 C32 2.6(7) . . . . ? C30 C31 C32 C33 -1.6(7) . . . . ? C31 C32 C33 C34 -0.4(7) . . . . ? C30 C29 C34 C33 -0.3(6) . . . . ? C28 C29 C34 C33 171.7(4) . . . . ? C32 C33 C34 C29 1.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.461 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.093 #===END