data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Lawson, Christopher' 'Slawin, Alexandra' 'Westwood, Nick' _publ_contact_author_name 'Westwood, Nick' _publ_contact_author_email njw3@st-andrews.ac.uk _publ_section_title ; Application of the copper catalysed N-arylation of amidines in the synthesis of analogues of the chemical tool, Blebbistatin ; # Attachment '- 8A..cif' data_8A _database_code_depnum_ccdc_archive 'CCDC 791559' #TrackingRef '- 8A..cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N2 O' _chemical_formula_sum 'C14 H14 N2 O' _chemical_formula_weight 226.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.425(6) _cell_length_b 10.594(3) _cell_length_c 8.249(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.152(10) _cell_angle_gamma 90.00 _cell_volume 1164.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3772 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.3 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.788 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6910 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2074 _reflns_number_gt 1770 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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. The NH hydrogen atoms were located from a difference map and refined isotropically subject to a distance restraint. ; _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^)+(0.0967P)^2^+0.4894P] 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 0.015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2074 _refine_ls_number_parameters 165 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 0.821 _refine_ls_restrained_S_all 0.822 _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 0.94094(9) 0.15665(12) 0.74354(15) 0.0225(3) Uani 1 1 d . . . C2 C 1.00197(11) 0.06105(14) 0.74752(17) 0.0214(4) Uani 1 1 d . . . N2 N 0.98166(10) -0.05875(12) 0.79313(17) 0.0272(4) Uani 1 1 d D . . H2A H 0.9159(11) -0.0780(17) 0.821(2) 0.037(5) Uiso 1 1 d D . . H2B H 1.0227(13) -0.1249(16) 0.771(2) 0.043(5) Uiso 1 1 d D . . C3 C 1.10567(11) 0.08481(14) 0.71007(18) 0.0213(4) Uani 1 1 d . . . C4 C 1.12442(11) 0.18173(14) 0.60199(18) 0.0223(4) Uani 1 1 d . . . H4A H 1.0700 0.2279 0.5461 0.027 Uiso 1 1 calc R . . C5 C 1.22163(12) 0.21034(14) 0.57646(19) 0.0262(4) Uani 1 1 d . . . H5A H 1.2337 0.2769 0.5043 0.031 Uiso 1 1 calc R . . C6 C 1.30217(12) 0.14204(15) 0.65600(19) 0.0270(4) Uani 1 1 d . . . H6A H 1.3690 0.1627 0.6393 0.032 Uiso 1 1 calc R . . C7 C 1.28416(12) 0.04414(15) 0.7593(2) 0.0265(4) Uani 1 1 d . . . H7A H 1.3387 -0.0038 0.8115 0.032 Uiso 1 1 calc R . . C8 C 1.18685(11) 0.01550(14) 0.78705(19) 0.0241(4) Uani 1 1 d . . . H8A H 1.1753 -0.0516 0.8588 0.029 Uiso 1 1 calc R . . C9 C 0.84079(11) 0.13855(13) 0.77769(17) 0.0214(4) Uani 1 1 d . . . C10 C 0.80281(11) 0.22187(14) 0.88488(18) 0.0228(4) Uani 1 1 d . . . H10A H 0.8453 0.2856 0.9365 0.027 Uiso 1 1 calc R . . C11 C 0.70389(11) 0.21387(14) 0.91813(19) 0.0250(4) Uani 1 1 d . . . H11A H 0.6795 0.2715 0.9921 0.030 Uiso 1 1 calc R . . C12 C 0.64087(11) 0.12151(14) 0.84299(19) 0.0238(4) Uani 1 1 d . . . C13 C 0.67713(11) 0.03847(15) 0.73331(19) 0.0254(4) Uani 1 1 d . . . H13A H 0.6342 -0.0246 0.6809 0.031 Uiso 1 1 calc R . . C14 C 0.77518(12) 0.04742(14) 0.70041(19) 0.0244(4) Uani 1 1 d . . . H14A H 0.7987 -0.0090 0.6242 0.029 Uiso 1 1 calc R . . O12 O 0.54230(8) 0.10481(11) 0.86914(14) 0.0313(3) Uani 1 1 d . . . C15 C 0.50434(12) 0.18839(16) 0.9827(2) 0.0337(4) Uani 1 1 d . . . H15A H 0.5458 0.1818 1.0889 0.050 Uiso 1 1 calc R . . H15B H 0.4349 0.1654 0.9946 0.050 Uiso 1 1 calc R . . H15C H 0.5063 0.2753 0.9424 0.050 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 0.0215(7) 0.0208(7) 0.0255(7) -0.0005(5) 0.0048(5) 0.0015(5) C2 0.0222(8) 0.0215(9) 0.0202(8) -0.0013(6) 0.0016(6) -0.0015(6) N2 0.0249(8) 0.0190(8) 0.0392(8) 0.0035(6) 0.0099(6) 0.0012(5) C3 0.0240(8) 0.0192(8) 0.0210(8) -0.0042(6) 0.0038(6) -0.0003(6) C4 0.0251(8) 0.0188(8) 0.0230(8) -0.0019(6) 0.0027(6) 0.0026(6) C5 0.0310(9) 0.0223(8) 0.0263(9) -0.0010(6) 0.0081(6) -0.0026(7) C6 0.0231(8) 0.0285(9) 0.0304(9) -0.0050(7) 0.0070(6) -0.0034(6) C7 0.0244(9) 0.0251(9) 0.0296(9) -0.0021(6) 0.0021(6) 0.0034(6) C8 0.0248(8) 0.0214(8) 0.0261(8) 0.0011(6) 0.0028(6) 0.0008(6) C9 0.0213(8) 0.0205(8) 0.0222(8) 0.0050(6) 0.0027(6) 0.0019(6) C10 0.0236(8) 0.0193(8) 0.0252(8) 0.0006(6) 0.0014(6) -0.0001(6) C11 0.0257(8) 0.0250(9) 0.0245(8) -0.0018(6) 0.0039(6) 0.0028(6) C12 0.0187(8) 0.0267(8) 0.0261(8) 0.0035(6) 0.0031(6) 0.0008(6) C13 0.0243(9) 0.0230(9) 0.0286(9) -0.0013(6) 0.0019(6) -0.0023(6) C14 0.0258(8) 0.0226(8) 0.0249(8) -0.0016(6) 0.0037(6) 0.0014(6) O12 0.0218(6) 0.0357(7) 0.0375(7) -0.0091(5) 0.0082(5) -0.0021(5) C15 0.0252(9) 0.0374(10) 0.0399(10) -0.0083(7) 0.0100(7) 0.0019(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 C2 1.301(2) . ? N1 C9 1.421(2) . ? C2 N2 1.361(2) . ? C2 C3 1.485(2) . ? N2 H2A 0.962(14) . ? N2 H2B 0.924(15) . ? C3 C8 1.399(2) . ? C3 C4 1.403(2) . ? C4 C5 1.381(2) . ? C4 H4A 0.9500 . ? C5 C6 1.395(2) . ? C5 H5A 0.9500 . ? C6 C7 1.382(2) . ? C6 H6A 0.9500 . ? C7 C8 1.388(2) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 C10 1.390(2) . ? C9 C14 1.405(2) . ? C10 C11 1.392(2) . ? C10 H10A 0.9500 . ? C11 C12 1.388(2) . ? C11 H11A 0.9500 . ? C12 O12 1.3784(19) . ? C12 C13 1.393(2) . ? C13 C14 1.380(2) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? O12 C15 1.4281(19) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C2 N1 C9 119.91(13) . . ? N1 C2 N2 125.87(14) . . ? N1 C2 C3 117.83(13) . . ? N2 C2 C3 116.17(13) . . ? C2 N2 H2A 119.0(11) . . ? C2 N2 H2B 120.4(12) . . ? H2A N2 H2B 118.4(16) . . ? C8 C3 C4 118.76(14) . . ? C8 C3 C2 120.95(14) . . ? C4 C3 C2 120.23(13) . . ? C5 C4 C3 120.34(14) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 120.41(15) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C7 C6 C5 119.61(15) . . ? C7 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C6 C7 C8 120.42(14) . . ? C6 C7 H7A 119.8 . . ? C8 C7 H7A 119.8 . . ? C7 C8 C3 120.42(14) . . ? C7 C8 H8A 119.8 . . ? C3 C8 H8A 119.8 . . ? C10 C9 C14 117.77(14) . . ? C10 C9 N1 118.13(13) . . ? C14 C9 N1 123.92(13) . . ? C9 C10 C11 121.41(14) . . ? C9 C10 H10A 119.3 . . ? C11 C10 H10A 119.3 . . ? C12 C11 C10 119.90(14) . . ? C12 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? O12 C12 C11 124.35(14) . . ? O12 C12 C13 116.15(13) . . ? C11 C12 C13 119.50(14) . . ? C14 C13 C12 120.24(14) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C13 C14 C9 121.16(14) . . ? C13 C14 H14A 119.4 . . ? C9 C14 H14A 119.4 . . ? C12 O12 C15 116.81(12) . . ? O12 C15 H15A 109.5 . . ? O12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C9 N1 C2 N2 -4.7(2) . . . . ? C9 N1 C2 C3 179.69(12) . . . . ? N1 C2 C3 C8 146.53(15) . . . . ? N2 C2 C3 C8 -29.5(2) . . . . ? N1 C2 C3 C4 -30.5(2) . . . . ? N2 C2 C3 C4 153.53(14) . . . . ? C8 C3 C4 C5 -2.0(2) . . . . ? C2 C3 C4 C5 175.07(13) . . . . ? C3 C4 C5 C6 0.9(2) . . . . ? C4 C5 C6 C7 0.8(2) . . . . ? C5 C6 C7 C8 -1.5(2) . . . . ? C6 C7 C8 C3 0.4(2) . . . . ? C4 C3 C8 C7 1.3(2) . . . . ? C2 C3 C8 C7 -175.71(14) . . . . ? C2 N1 C9 C10 133.18(14) . . . . ? C2 N1 C9 C14 -51.8(2) . . . . ? C14 C9 C10 C11 1.5(2) . . . . ? N1 C9 C10 C11 176.85(13) . . . . ? C9 C10 C11 C12 -0.3(2) . . . . ? C10 C11 C12 O12 179.20(13) . . . . ? C10 C11 C12 C13 -0.7(2) . . . . ? O12 C12 C13 C14 -179.52(13) . . . . ? C11 C12 C13 C14 0.4(2) . . . . ? C12 C13 C14 C9 0.9(2) . . . . ? C10 C9 C14 C13 -1.9(2) . . . . ? N1 C9 C14 C13 -176.87(13) . . . . ? C11 C12 O12 C15 -0.6(2) . . . . ? C13 C12 O12 C15 179.34(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 N2 H2B N1 0.924(15) 2.371(16) 3.216(2) 151.8(16) 2_746 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.217 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.049 # Attachment '- 8B.CIF' data_8B _database_code_depnum_ccdc_archive 'CCDC 791560' #TrackingRef '- 8B.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N2' _chemical_formula_sum 'C14 H14 N2' _chemical_formula_weight 210.27 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 9.820(2) _cell_length_b 10.097(3) _cell_length_c 12.209(4) _cell_angle_alpha 84.126(18) _cell_angle_beta 81.77(2) _cell_angle_gamma 80.108(17) _cell_volume 1176.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3754 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 28.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.646 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7473 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4141 _reflns_number_gt 3120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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. The NH hydrogen atoms were located from a difference map and refined isotropically subject to a distance restraint. ; _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^)+(0.0757P)^2^+0.0137P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4141 _refine_ls_number_parameters 308 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1577 _refine_ls_wR_factor_gt 0.1388 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.005 _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 0.31623(14) 0.08127(15) -0.09592(13) 0.0248(4) Uani 1 1 d . . . C2 C 0.28743(17) 0.18570(17) -0.03796(15) 0.0215(4) Uani 1 1 d . . . N2 N 0.34812(16) 0.29742(15) -0.06104(15) 0.0307(4) Uani 1 1 d D . . H2A H 0.4090(17) 0.2997(19) -0.1268(14) 0.028(5) Uiso 1 1 d D . . H2B H 0.3074(19) 0.3782(17) -0.0266(16) 0.038(5) Uiso 1 1 d D . . C3 C 0.18377(17) 0.18269(17) 0.06372(15) 0.0230(4) Uani 1 1 d . . . C4 C 0.08695(17) 0.09478(19) 0.07540(16) 0.0280(5) Uani 1 1 d . . . H4A H 0.0872 0.0378 0.0181 0.034 Uiso 1 1 calc R . . C5 C -0.00989(18) 0.0893(2) 0.16972(18) 0.0335(5) Uani 1 1 d . . . H5A H -0.0749 0.0283 0.1767 0.040 Uiso 1 1 calc R . . C6 C -0.01208(19) 0.1725(2) 0.25377(18) 0.0359(5) Uani 1 1 d . . . H6A H -0.0785 0.1690 0.3183 0.043 Uiso 1 1 calc R . . C7 C 0.0834(2) 0.2606(2) 0.24275(17) 0.0344(5) Uani 1 1 d . . . H7A H 0.0822 0.3182 0.2999 0.041 Uiso 1 1 calc R . . C8 C 0.18125(18) 0.26552(18) 0.14829(16) 0.0288(5) Uani 1 1 d . . . H8A H 0.2467 0.3260 0.1417 0.035 Uiso 1 1 calc R . . C9 C 0.41903(17) 0.08566(17) -0.19150(16) 0.0230(4) Uani 1 1 d . . . C10 C 0.38152(18) 0.10743(18) -0.29743(16) 0.0266(5) Uani 1 1 d . . . H10A H 0.2858 0.1226 -0.3076 0.032 Uiso 1 1 calc R . . C11 C 0.48357(18) 0.10731(19) -0.38954(17) 0.0294(5) Uani 1 1 d . . . H11A H 0.4559 0.1232 -0.4618 0.035 Uiso 1 1 calc R . . C12 C 0.62442(18) 0.08463(18) -0.37830(17) 0.0283(5) Uani 1 1 d . . . C13 C 0.66111(18) 0.06062(18) -0.27160(17) 0.0292(5) Uani 1 1 d . . . H13A H 0.7569 0.0435 -0.2616 0.035 Uiso 1 1 calc R . . C14 C 0.56031(18) 0.06116(18) -0.17899(17) 0.0278(5) Uani 1 1 d . . . H14A H 0.5880 0.0447 -0.1067 0.033 Uiso 1 1 calc R . . C15 C 0.73532(19) 0.0845(2) -0.47821(18) 0.0386(5) Uani 1 1 d . . . H15A H 0.7750 0.1681 -0.4849 0.058 Uiso 1 1 calc R . . H15B H 0.6936 0.0783 -0.5454 0.058 Uiso 1 1 calc R . . H15C H 0.8091 0.0071 -0.4690 0.058 Uiso 1 1 calc R . . N21 N 0.24145(15) 0.57462(15) 0.01598(14) 0.0278(4) Uani 1 1 d . . . C22 C 0.28762(17) 0.67633(18) -0.04177(17) 0.0256(4) Uani 1 1 d . . . N22 N 0.28164(16) 0.79887(16) -0.00345(15) 0.0306(4) Uani 1 1 d D . . H22A H 0.2405(18) 0.808(2) 0.0735(13) 0.035(5) Uiso 1 1 d D . . H22B H 0.301(2) 0.876(2) -0.0507(18) 0.062(7) Uiso 1 1 d D . . C23 C 0.35438(18) 0.66001(18) -0.15829(17) 0.0273(5) Uani 1 1 d . . . C24 C 0.30451(19) 0.57843(19) -0.22340(17) 0.0316(5) Uani 1 1 d . . . H24A H 0.2275 0.5346 -0.1937 0.038 Uiso 1 1 calc R . . C25 C 0.3664(2) 0.5606(2) -0.33135(18) 0.0378(5) Uani 1 1 d . . . H25A H 0.3326 0.5037 -0.3749 0.045 Uiso 1 1 calc R . . C26 C 0.4778(2) 0.6258(2) -0.37613(19) 0.0392(5) Uani 1 1 d . . . H26A H 0.5201 0.6137 -0.4502 0.047 Uiso 1 1 calc R . . C27 C 0.5267(2) 0.7082(2) -0.31244(18) 0.0364(5) Uani 1 1 d . . . H27A H 0.6028 0.7530 -0.3429 0.044 Uiso 1 1 calc R . . C28 C 0.46519(18) 0.72631(19) -0.20373(17) 0.0304(5) Uani 1 1 d . . . H28A H 0.4988 0.7839 -0.1606 0.037 Uiso 1 1 calc R . . C29 C 0.17351(19) 0.59850(18) 0.12474(17) 0.0275(5) Uani 1 1 d . . . C30 C 0.02797(19) 0.62245(18) 0.14420(18) 0.0317(5) Uani 1 1 d . . . H30A H -0.0249 0.6223 0.0849 0.038 Uiso 1 1 calc R . . C31 C -0.0398(2) 0.6465(2) 0.25004(19) 0.0361(5) Uani 1 1 d . . . H31A H -0.1387 0.6630 0.2616 0.043 Uiso 1 1 calc R . . C32 C 0.0330(2) 0.6471(2) 0.33919(18) 0.0363(5) Uani 1 1 d . . . C33 C 0.1779(2) 0.6192(2) 0.31968(18) 0.0359(5) Uani 1 1 d . . . H33A H 0.2305 0.6164 0.3796 0.043 Uiso 1 1 calc R . . C34 C 0.2473(2) 0.59547(19) 0.21398(18) 0.0336(5) Uani 1 1 d . . . H34A H 0.3462 0.5770 0.2029 0.040 Uiso 1 1 calc R . . C35 C -0.0413(2) 0.6776(2) 0.4529(2) 0.0524(7) Uani 1 1 d . . . H35A H -0.0628 0.7754 0.4573 0.079 Uiso 1 1 calc R . . H35B H 0.0186 0.6376 0.5093 0.079 Uiso 1 1 calc R . . H35C H -0.1281 0.6395 0.4659 0.079 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 0.0295(8) 0.0242(8) 0.0205(10) -0.0018(7) -0.0006(6) -0.0062(6) C2 0.0244(9) 0.0205(9) 0.0199(11) -0.0018(8) -0.0039(7) -0.0035(7) N2 0.0363(9) 0.0229(9) 0.0312(11) -0.0072(8) 0.0092(8) -0.0080(7) C3 0.0259(9) 0.0189(9) 0.0226(11) 0.0013(8) -0.0026(8) -0.0009(7) C4 0.0288(9) 0.0297(10) 0.0260(12) -0.0047(9) -0.0015(8) -0.0062(8) C5 0.0276(10) 0.0396(12) 0.0333(13) 0.0017(10) -0.0003(9) -0.0106(8) C6 0.0357(11) 0.0382(12) 0.0282(13) 0.0020(9) 0.0061(9) -0.0016(9) C7 0.0478(12) 0.0292(11) 0.0236(13) -0.0046(9) 0.0014(9) -0.0023(9) C8 0.0366(10) 0.0224(10) 0.0270(12) -0.0006(8) -0.0027(8) -0.0058(8) C9 0.0302(10) 0.0178(9) 0.0207(11) -0.0002(8) 0.0004(8) -0.0070(7) C10 0.0268(9) 0.0266(10) 0.0253(12) -0.0036(8) -0.0001(8) -0.0025(7) C11 0.0392(11) 0.0289(11) 0.0194(11) -0.0018(8) -0.0040(8) -0.0036(8) C12 0.0311(10) 0.0241(10) 0.0276(12) -0.0026(8) 0.0042(8) -0.0051(8) C13 0.0281(10) 0.0272(11) 0.0320(13) -0.0015(9) -0.0037(8) -0.0046(8) C14 0.0348(10) 0.0261(10) 0.0232(11) -0.0012(8) -0.0046(8) -0.0066(8) C15 0.0382(11) 0.0458(13) 0.0310(13) -0.0050(10) 0.0031(9) -0.0093(9) N21 0.0365(9) 0.0225(9) 0.0242(10) -0.0043(7) 0.0019(7) -0.0077(7) C22 0.0260(9) 0.0231(10) 0.0282(12) -0.0020(8) -0.0046(8) -0.0042(7) N22 0.0425(9) 0.0231(9) 0.0261(11) -0.0033(8) 0.0008(8) -0.0083(7) C23 0.0327(10) 0.0208(10) 0.0268(12) 0.0012(8) -0.0027(8) -0.0024(8) C24 0.0411(11) 0.0269(10) 0.0273(13) -0.0001(9) -0.0034(9) -0.0092(8) C25 0.0510(12) 0.0341(12) 0.0291(14) -0.0049(10) -0.0027(10) -0.0100(9) C26 0.0518(12) 0.0361(12) 0.0257(13) -0.0023(10) 0.0048(10) -0.0038(10) C27 0.0392(11) 0.0330(12) 0.0356(14) 0.0032(10) 0.0001(9) -0.0092(9) C28 0.0352(10) 0.0272(10) 0.0291(13) -0.0016(9) -0.0040(9) -0.0061(8) C29 0.0403(11) 0.0161(9) 0.0252(12) -0.0008(8) 0.0006(9) -0.0067(7) C30 0.0393(11) 0.0240(10) 0.0307(13) -0.0013(9) -0.0036(9) -0.0035(8) C31 0.0382(11) 0.0286(11) 0.0392(14) -0.0039(10) 0.0021(10) -0.0042(8) C32 0.0537(13) 0.0246(11) 0.0277(13) -0.0043(9) 0.0062(10) -0.0065(9) C33 0.0520(13) 0.0315(11) 0.0257(13) -0.0025(9) -0.0037(9) -0.0122(9) C34 0.0406(11) 0.0285(11) 0.0320(13) -0.0021(9) -0.0017(9) -0.0094(8) C35 0.0700(15) 0.0463(14) 0.0371(16) -0.0090(12) 0.0087(12) -0.0084(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 N1 C2 1.298(2) . ? N1 C9 1.432(2) . ? C2 N2 1.351(2) . ? C2 C3 1.490(2) . ? C3 C8 1.389(3) . ? C3 C4 1.392(3) . ? C4 C5 1.387(3) . ? C5 C6 1.387(3) . ? C6 C7 1.384(3) . ? C7 C8 1.394(3) . ? C9 C10 1.381(3) . ? C9 C14 1.394(2) . ? C10 C11 1.395(3) . ? C11 C12 1.387(3) . ? C12 C13 1.388(3) . ? C12 C15 1.514(3) . ? C13 C14 1.392(3) . ? N21 C22 1.295(2) . ? N21 C29 1.422(2) . ? C22 N22 1.356(2) . ? C22 C23 1.491(3) . ? C23 C24 1.391(3) . ? C23 C28 1.393(3) . ? C24 C25 1.386(3) . ? C25 C26 1.390(3) . ? C26 C27 1.380(3) . ? C27 C28 1.394(3) . ? C29 C34 1.387(3) . ? C29 C30 1.398(3) . ? C30 C31 1.391(3) . ? C31 C32 1.386(3) . ? C32 C33 1.392(3) . ? C32 C35 1.508(3) . ? C33 C34 1.394(3) . ? 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 C2 N1 C9 117.45(15) . . ? N1 C2 N2 124.67(17) . . ? N1 C2 C3 118.73(16) . . ? N2 C2 C3 116.56(16) . . ? C8 C3 C4 118.66(17) . . ? C8 C3 C2 121.59(17) . . ? C4 C3 C2 119.75(17) . . ? C5 C4 C3 120.85(19) . . ? C6 C5 C4 120.22(19) . . ? C7 C6 C5 119.38(19) . . ? C6 C7 C8 120.4(2) . . ? C3 C8 C7 120.51(18) . . ? C10 C9 C14 118.66(16) . . ? C10 C9 N1 121.22(15) . . ? C14 C9 N1 120.04(17) . . ? C9 C10 C11 120.29(17) . . ? C12 C11 C10 121.66(19) . . ? C11 C12 C13 117.62(17) . . ? C11 C12 C15 121.72(18) . . ? C13 C12 C15 120.66(17) . . ? C12 C13 C14 121.28(17) . . ? C13 C14 C9 120.47(18) . . ? C22 N21 C29 116.24(15) . . ? N21 C22 N22 124.55(18) . . ? N21 C22 C23 119.04(16) . . ? N22 C22 C23 116.40(17) . . ? C24 C23 C28 119.23(18) . . ? C24 C23 C22 119.62(17) . . ? C28 C23 C22 121.15(18) . . ? C25 C24 C23 120.42(19) . . ? C24 C25 C26 120.2(2) . . ? C27 C26 C25 119.6(2) . . ? C26 C27 C28 120.43(19) . . ? C23 C28 C27 120.03(19) . . ? C34 C29 C30 118.27(18) . . ? C34 C29 N21 122.02(16) . . ? C30 C29 N21 119.69(18) . . ? C31 C30 C29 120.28(19) . . ? C32 C31 C30 121.88(18) . . ? C31 C32 C33 117.42(18) . . ? C31 C32 C35 121.46(19) . . ? C33 C32 C35 121.1(2) . . ? C32 C33 C34 121.3(2) . . ? C29 C34 C33 120.78(18) . . ? 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 C9 N1 C2 N2 -0.5(3) . . . . ? C9 N1 C2 C3 -178.34(14) . . . . ? N1 C2 C3 C8 157.94(16) . . . . ? N2 C2 C3 C8 -20.1(2) . . . . ? N1 C2 C3 C4 -21.8(2) . . . . ? N2 C2 C3 C4 160.15(17) . . . . ? C8 C3 C4 C5 -0.3(3) . . . . ? C2 C3 C4 C5 179.45(16) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C4 C3 C8 C7 -0.1(3) . . . . ? C2 C3 C8 C7 -179.87(16) . . . . ? C6 C7 C8 C3 0.4(3) . . . . ? C2 N1 C9 C10 -104.3(2) . . . . ? C2 N1 C9 C14 78.8(2) . . . . ? C14 C9 C10 C11 -1.2(3) . . . . ? N1 C9 C10 C11 -178.07(16) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C10 C11 C12 C15 -179.97(18) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C15 C12 C13 C14 179.63(17) . . . . ? C12 C13 C14 C9 0.2(3) . . . . ? C10 C9 C14 C13 0.9(3) . . . . ? N1 C9 C14 C13 177.78(16) . . . . ? C29 N21 C22 N22 3.6(3) . . . . ? C29 N21 C22 C23 -177.33(15) . . . . ? N21 C22 C23 C24 35.4(2) . . . . ? N22 C22 C23 C24 -145.47(17) . . . . ? N21 C22 C23 C28 -145.33(18) . . . . ? N22 C22 C23 C28 33.8(2) . . . . ? C28 C23 C24 C25 1.6(3) . . . . ? C22 C23 C24 C25 -179.14(16) . . . . ? C23 C24 C25 C26 -0.9(3) . . . . ? C24 C25 C26 C27 0.1(3) . . . . ? C25 C26 C27 C28 0.1(3) . . . . ? C24 C23 C28 C27 -1.4(3) . . . . ? C22 C23 C28 C27 179.32(16) . . . . ? C26 C27 C28 C23 0.6(3) . . . . ? C22 N21 C29 C34 -82.0(2) . . . . ? C22 N21 C29 C30 99.7(2) . . . . ? C34 C29 C30 C31 1.9(3) . . . . ? N21 C29 C30 C31 -179.74(16) . . . . ? C29 C30 C31 C32 -0.3(3) . . . . ? C30 C31 C32 C33 -1.5(3) . . . . ? C30 C31 C32 C35 178.04(19) . . . . ? C31 C32 C33 C34 1.8(3) . . . . ? C35 C32 C33 C34 -177.80(19) . . . . ? C30 C29 C34 C33 -1.7(3) . . . . ? N21 C29 C34 C33 -179.98(17) . . . . ? C32 C33 C34 C29 -0.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2B N21 0.955(15) 2.073(16) 3.011(2) 167.0(18) . N22 H22B N1 0.954(17) 2.110(19) 3.014(2) 158(2) 1_565 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.237 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.051 # Attachment '- 9B.CIF' data_9B _database_code_depnum_ccdc_archive 'CCDC 791561' #TrackingRef '- 9B.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration unk _chemical_formula_moiety 'C21 H20 N2' _chemical_formula_sum 'C21 H20 N2' _chemical_formula_weight 300.39 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 P2(1)2(1)2(1) 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' _cell_length_a 11.356(2) _cell_length_b 16.525(4) _cell_length_c 18.416(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3455.9(12) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 10374 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 28.6 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21902 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.33 _reflns_number_total 6293 _reflns_number_gt 4926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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. The NH hydrogen atoms were located from a difference map and refined isotropically subject to a distance restraint. ; _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^)+(0.0557P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(3) _refine_ls_number_reflns 6293 _refine_ls_number_parameters 428 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.001 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 -0.01924(18) 0.27468(14) 0.73878(12) 0.0319(5) Uani 1 1 d D . . H1N H -0.005(2) 0.2376(16) 0.7783(12) 0.051(9) Uiso 1 1 d D . . C2 C 0.0763(2) 0.28762(16) 0.69448(14) 0.0290(6) Uani 1 1 d . . . N2 N 0.07729(18) 0.34645(13) 0.64783(11) 0.0295(5) Uani 1 1 d . . . C3 C 0.1764(2) 0.23093(16) 0.70895(13) 0.0291(6) Uani 1 1 d . . . C4 C 0.1612(3) 0.14771(17) 0.71002(13) 0.0333(6) Uani 1 1 d . . . H4A H 0.0852 0.1254 0.7020 0.040 Uiso 1 1 calc R . . C5 C 0.2567(3) 0.09649(18) 0.72280(14) 0.0404(7) Uani 1 1 d . . . H5A H 0.2464 0.0394 0.7232 0.048 Uiso 1 1 calc R . . C6 C 0.3669(3) 0.12995(19) 0.73484(17) 0.0463(8) Uani 1 1 d . . . H6A H 0.4326 0.0956 0.7429 0.056 Uiso 1 1 calc R . . C7 C 0.3820(3) 0.2129(2) 0.73519(17) 0.0489(8) Uani 1 1 d . . . H7A H 0.4576 0.2353 0.7443 0.059 Uiso 1 1 calc R . . C8 C 0.2874(2) 0.26326(19) 0.72228(15) 0.0397(7) Uani 1 1 d . . . H8A H 0.2982 0.3203 0.7225 0.048 Uiso 1 1 calc R . . C9 C -0.1298(2) 0.31373(16) 0.73587(15) 0.0325(6) Uani 1 1 d . . . C10 C -0.1781(2) 0.34421(17) 0.67184(16) 0.0374(7) Uani 1 1 d . . . H10A H -0.1337 0.3424 0.6281 0.045 Uiso 1 1 calc R . . C11 C -0.2897(3) 0.37686(18) 0.6715(2) 0.0470(8) Uani 1 1 d . . . H11A H -0.3207 0.3973 0.6273 0.056 Uiso 1 1 calc R . . C12 C -0.3575(3) 0.38075(19) 0.7331(2) 0.0518(9) Uani 1 1 d . . . C13 C -0.3091(3) 0.35128(18) 0.7975(2) 0.0523(9) Uani 1 1 d . . . H13A H -0.3540 0.3538 0.8409 0.063 Uiso 1 1 calc R . . C14 C -0.1954(2) 0.31796(18) 0.79949(17) 0.0411(7) Uani 1 1 d . . . H14A H -0.1636 0.2985 0.8439 0.049 Uiso 1 1 calc R . . C15 C -0.4812(3) 0.4160(2) 0.7312(3) 0.0793(13) Uani 1 1 d . . . H15A H -0.4777 0.4725 0.7150 0.119 Uiso 1 1 calc R . . H15B H -0.5158 0.4136 0.7799 0.119 Uiso 1 1 calc R . . H15C H -0.5299 0.3847 0.6974 0.119 Uiso 1 1 calc R . . C16 C 0.1712(2) 0.35183(16) 0.59693(13) 0.0295(6) Uani 1 1 d . . . C17 C 0.1882(3) 0.29273(18) 0.54477(16) 0.0472(8) Uani 1 1 d . . . H17A H 0.1379 0.2468 0.5441 0.057 Uiso 1 1 calc R . . C18 C 0.2770(3) 0.2990(2) 0.49354(16) 0.0505(8) Uani 1 1 d . . . H18A H 0.2867 0.2572 0.4586 0.061 Uiso 1 1 calc R . . C19 C 0.3516(2) 0.36500(17) 0.49229(15) 0.0357(7) Uani 1 1 d . . . C20 C 0.3332(2) 0.42484(18) 0.54374(15) 0.0378(7) Uani 1 1 d . . . H20A H 0.3835 0.4708 0.5442 0.045 Uiso 1 1 calc R . . C21 C 0.2434(2) 0.41945(17) 0.59451(15) 0.0349(6) Uani 1 1 d . . . H21A H 0.2313 0.4624 0.6279 0.042 Uiso 1 1 calc R . . C22 C 0.4491(3) 0.3721(2) 0.43743(16) 0.0455(8) Uani 1 1 d . . . H22A H 0.4379 0.4213 0.4085 0.068 Uiso 1 1 calc R . . H22B H 0.4480 0.3247 0.4054 0.068 Uiso 1 1 calc R . . H22C H 0.5250 0.3748 0.4626 0.068 Uiso 1 1 calc R . . N31 N -0.0096(2) 0.02707(15) 0.81831(12) 0.0387(6) Uani 1 1 d D . . H31N H 0.010(3) -0.0291(13) 0.8304(19) 0.084(12) Uiso 1 1 d D . . C32 C 0.0297(2) 0.08111(19) 0.86863(15) 0.0380(7) Uani 1 1 d . . . N32 N -0.0002(2) 0.15812(14) 0.86452(12) 0.0360(6) Uani 1 1 d . . . C33 C 0.1107(2) 0.04495(17) 0.92441(14) 0.0339(6) Uani 1 1 d . . . C34 C 0.0820(3) -0.02169(18) 0.96570(15) 0.0400(7) Uani 1 1 d . . . H34A H 0.0093 -0.0486 0.9572 0.048 Uiso 1 1 calc R . . C35 C 0.1557(3) -0.0501(2) 1.01876(16) 0.0498(8) Uani 1 1 d . . . H35A H 0.1341 -0.0961 1.0467 0.060 Uiso 1 1 calc R . . C36 C 0.2603(3) -0.0118(2) 1.03116(16) 0.0532(9) Uani 1 1 d . . . H36A H 0.3103 -0.0311 1.0687 0.064 Uiso 1 1 calc R . . C37 C 0.2949(3) 0.0533(2) 0.99104(17) 0.0522(9) Uani 1 1 d . . . H37A H 0.3686 0.0787 0.9999 0.063 Uiso 1 1 calc R . . C38 C 0.2194(3) 0.0824(2) 0.93606(16) 0.0440(8) Uani 1 1 d . . . H38A H 0.2423 0.1273 0.9071 0.053 Uiso 1 1 calc R . . C39 C -0.1002(2) 0.03585(17) 0.76615(13) 0.0307(6) Uani 1 1 d . . . C40 C -0.1791(2) 0.09999(17) 0.76190(14) 0.0349(7) Uani 1 1 d . . . H40A H -0.1717 0.1445 0.7942 0.042 Uiso 1 1 calc R . . C41 C -0.2684(2) 0.09934(19) 0.71088(15) 0.0407(7) Uani 1 1 d . . . H41A H -0.3206 0.1442 0.7086 0.049 Uiso 1 1 calc R . . C42 C -0.2842(3) 0.03603(19) 0.66335(14) 0.0399(7) Uani 1 1 d . . . C43 C -0.2065(3) -0.02777(19) 0.66683(15) 0.0423(7) Uani 1 1 d . . . H43A H -0.2161 -0.0724 0.6349 0.051 Uiso 1 1 calc R . . C44 C -0.1129(3) -0.02802(18) 0.71702(14) 0.0396(7) Uani 1 1 d . . . H44A H -0.0583 -0.0716 0.7175 0.048 Uiso 1 1 calc R . . C45 C -0.3837(3) 0.0370(2) 0.60781(16) 0.0552(9) Uani 1 1 d . . . H45A H -0.4432 0.0768 0.6225 0.083 Uiso 1 1 calc R . . H45B H -0.4199 -0.0167 0.6052 0.083 Uiso 1 1 calc R . . H45C H -0.3522 0.0517 0.5601 0.083 Uiso 1 1 calc R . . C46 C 0.0227(2) 0.20658(16) 0.92642(14) 0.0336(6) Uani 1 1 d . . . C47 C -0.0348(2) 0.19273(18) 0.99213(14) 0.0374(7) Uani 1 1 d . . . H47A H -0.0882 0.1487 0.9963 0.045 Uiso 1 1 calc R . . C48 C -0.0148(3) 0.24232(19) 1.05113(16) 0.0412(7) Uani 1 1 d . . . H48A H -0.0550 0.2316 1.0953 0.049 Uiso 1 1 calc R . . C49 C 0.0619(3) 0.30723(18) 1.04785(14) 0.0386(7) Uani 1 1 d . . . C50 C 0.1167(3) 0.32200(18) 0.98197(14) 0.0412(7) Uani 1 1 d . . . H50A H 0.1686 0.3669 0.9780 0.049 Uiso 1 1 calc R . . C51 C 0.0981(3) 0.27312(18) 0.92136(15) 0.0422(7) Uani 1 1 d . . . H51A H 0.1365 0.2850 0.8768 0.051 Uiso 1 1 calc R . . C52 C 0.0840(3) 0.3602(2) 1.11321(15) 0.0518(9) Uani 1 1 d . . . H52A H 0.1551 0.3926 1.1052 0.078 Uiso 1 1 calc R . . H52B H 0.0949 0.3262 1.1563 0.078 Uiso 1 1 calc R . . H52C H 0.0165 0.3962 1.1206 0.078 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 0.0312(12) 0.0295(13) 0.0351(12) 0.0028(10) 0.0029(11) 0.0007(10) C2 0.0285(14) 0.0256(15) 0.0329(13) -0.0016(12) 0.0007(12) -0.0028(11) N2 0.0323(12) 0.0251(12) 0.0313(11) 0.0000(10) 0.0021(10) -0.0019(10) C3 0.0315(14) 0.0284(15) 0.0274(13) -0.0001(11) 0.0017(11) 0.0018(11) C4 0.0408(15) 0.0299(16) 0.0290(14) -0.0009(12) 0.0015(12) 0.0010(12) C5 0.0548(19) 0.0298(17) 0.0366(15) 0.0004(12) -0.0007(14) 0.0105(14) C6 0.0393(17) 0.047(2) 0.0527(18) 0.0110(15) -0.0003(15) 0.0155(15) C7 0.0329(15) 0.050(2) 0.063(2) 0.0105(17) -0.0036(15) 0.0056(14) C8 0.0378(16) 0.0366(18) 0.0447(16) 0.0076(14) -0.0022(14) -0.0020(13) C9 0.0283(14) 0.0240(15) 0.0452(16) -0.0030(12) 0.0026(13) 0.0007(11) C10 0.0315(15) 0.0310(17) 0.0496(17) 0.0023(13) -0.0014(13) -0.0014(12) C11 0.0330(16) 0.0329(18) 0.075(2) 0.0014(16) -0.0060(17) 0.0010(13) C12 0.0347(16) 0.0258(17) 0.095(3) -0.0071(17) 0.0005(19) 0.0018(13) C13 0.0437(19) 0.0304(18) 0.083(2) -0.0156(18) 0.0253(19) -0.0077(14) C14 0.0379(16) 0.0322(16) 0.0531(18) -0.0071(14) 0.0117(15) -0.0026(13) C15 0.0324(17) 0.042(2) 0.164(4) -0.008(2) 0.003(2) 0.0057(15) C16 0.0321(14) 0.0264(15) 0.0300(14) 0.0005(12) -0.0015(12) 0.0027(11) C17 0.0588(19) 0.0338(18) 0.0489(17) -0.0079(14) 0.0157(16) -0.0158(15) C18 0.066(2) 0.041(2) 0.0446(17) -0.0067(14) 0.0208(17) -0.0044(16) C19 0.0329(15) 0.0378(18) 0.0366(15) 0.0046(12) 0.0054(13) 0.0070(13) C20 0.0370(15) 0.0370(17) 0.0395(15) -0.0023(14) 0.0043(14) -0.0022(13) C21 0.0379(15) 0.0274(16) 0.0393(15) -0.0062(12) 0.0047(13) 0.0009(12) C22 0.0401(16) 0.050(2) 0.0461(18) 0.0076(14) 0.0100(14) 0.0109(15) N31 0.0422(14) 0.0346(15) 0.0392(13) 0.0028(11) -0.0023(11) -0.0046(12) C32 0.0380(15) 0.0420(19) 0.0340(15) 0.0005(13) 0.0026(13) -0.0020(14) N32 0.0472(14) 0.0253(13) 0.0354(12) 0.0017(10) 0.0072(11) -0.0038(11) C33 0.0361(15) 0.0358(17) 0.0297(14) -0.0002(12) 0.0015(13) 0.0038(13) C34 0.0459(17) 0.0339(17) 0.0402(16) -0.0019(13) 0.0030(14) -0.0022(14) C35 0.060(2) 0.047(2) 0.0422(17) 0.0082(15) 0.0056(16) 0.0116(17) C36 0.054(2) 0.068(2) 0.0376(17) 0.0040(17) -0.0050(16) 0.0226(19) C37 0.0310(16) 0.067(2) 0.059(2) -0.0118(19) -0.0040(16) 0.0003(16) C38 0.0413(17) 0.0436(19) 0.0470(18) 0.0051(15) 0.0087(15) 0.0003(15) C39 0.0328(14) 0.0338(16) 0.0254(13) 0.0063(11) -0.0023(12) -0.0047(12) C40 0.0382(15) 0.0335(17) 0.0330(14) -0.0045(12) 0.0058(13) -0.0063(13) C41 0.0381(16) 0.0414(19) 0.0426(17) 0.0073(14) 0.0034(14) 0.0026(13) C42 0.0386(16) 0.051(2) 0.0304(15) 0.0041(14) 0.0000(13) -0.0061(15) C43 0.0578(19) 0.0372(18) 0.0320(15) -0.0084(13) 0.0024(15) -0.0100(15) C44 0.0529(17) 0.0298(16) 0.0361(15) 0.0014(12) 0.0066(14) 0.0065(14) C45 0.0511(19) 0.069(2) 0.0452(18) -0.0042(16) -0.0059(16) -0.0046(18) C46 0.0405(15) 0.0298(15) 0.0304(14) 0.0032(12) -0.0010(13) 0.0020(12) C47 0.0362(15) 0.0348(17) 0.0411(16) 0.0074(13) 0.0052(14) -0.0020(13) C48 0.0433(17) 0.050(2) 0.0306(14) 0.0037(13) 0.0032(13) 0.0019(15) C49 0.0438(17) 0.0403(19) 0.0316(14) 0.0015(13) -0.0063(13) 0.0024(14) C50 0.0514(18) 0.0356(17) 0.0367(15) 0.0031(12) -0.0028(14) -0.0099(14) C51 0.0537(18) 0.0380(18) 0.0350(15) 0.0071(13) 0.0056(15) -0.0129(15) C52 0.067(2) 0.052(2) 0.0367(16) -0.0003(15) -0.0043(16) -0.0054(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 N1 C2 1.374(3) . ? N1 C9 1.413(3) . ? N1 H1N 0.964(17) . ? C2 N2 1.297(3) . ? C2 C3 1.497(3) . ? N2 C16 1.422(3) . ? C3 C4 1.386(4) . ? C3 C8 1.391(4) . ? C4 C5 1.396(4) . ? C4 H4A 0.9500 . ? C5 C6 1.385(4) . ? C5 H5A 0.9500 . ? C6 C7 1.382(4) . ? C6 H6A 0.9500 . ? C7 C8 1.379(4) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 C14 1.390(4) . ? C9 C10 1.395(4) . ? C10 C11 1.377(4) . ? C10 H10A 0.9500 . ? C11 C12 1.371(5) . ? C11 H11A 0.9500 . ? C12 C13 1.395(5) . ? C12 C15 1.522(4) . ? C13 C14 1.404(4) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.383(4) . ? C16 C21 1.387(4) . ? C17 C18 1.384(4) . ? C17 H17A 0.9500 . ? C18 C19 1.381(4) . ? C18 H18A 0.9500 . ? C19 C20 1.385(4) . ? C19 C22 1.504(4) . ? C20 C21 1.386(4) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N31 C32 1.362(4) . ? N31 C39 1.415(3) . ? N31 H31N 0.981(18) . ? C32 N32 1.319(4) . ? C32 C33 1.503(4) . ? N32 C46 1.417(3) . ? C33 C34 1.377(4) . ? C33 C38 1.397(4) . ? C34 C35 1.369(4) . ? C34 H34A 0.9500 . ? C35 C36 1.365(5) . ? C35 H35A 0.9500 . ? C36 C37 1.364(5) . ? C36 H36A 0.9500 . ? C37 C38 1.412(4) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C39 C40 1.390(4) . ? C39 C44 1.398(4) . ? C40 C41 1.382(4) . ? C40 H40A 0.9500 . ? C41 C42 1.376(4) . ? C41 H41A 0.9500 . ? C42 C43 1.376(4) . ? C42 C45 1.525(4) . ? C43 C44 1.408(4) . ? C43 H43A 0.9500 . ? C44 H44A 0.9500 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C47 1.394(4) . ? C46 C51 1.397(4) . ? C47 C48 1.380(4) . ? C47 H47A 0.9500 . ? C48 C49 1.384(4) . ? C48 H48A 0.9500 . ? C49 C50 1.385(4) . ? C49 C52 1.509(4) . ? C50 C51 1.394(4) . ? C50 H50A 0.9500 . ? C51 H51A 0.9500 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? 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 C2 N1 C9 127.4(2) . . ? C2 N1 H1N 114.6(17) . . ? C9 N1 H1N 117.8(17) . . ? N2 C2 N1 121.1(2) . . ? N2 C2 C3 125.5(2) . . ? N1 C2 C3 113.4(2) . . ? C2 N2 C16 119.3(2) . . ? C4 C3 C8 119.4(3) . . ? C4 C3 C2 121.9(2) . . ? C8 C3 C2 118.6(2) . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C7 C8 C3 120.3(3) . . ? C7 C8 H8A 119.9 . . ? C3 C8 H8A 119.9 . . ? C14 C9 C10 118.9(2) . . ? C14 C9 N1 117.9(2) . . ? C10 C9 N1 123.1(2) . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C12 C11 C10 122.1(3) . . ? C12 C11 H11A 118.9 . . ? C10 C11 H11A 118.9 . . ? C11 C12 C13 117.7(3) . . ? C11 C12 C15 121.1(4) . . ? C13 C12 C15 121.2(4) . . ? C12 C13 C14 121.5(3) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C9 C14 C13 119.3(3) . . ? C9 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 117.6(2) . . ? C17 C16 N2 121.2(2) . . ? C21 C16 N2 121.0(2) . . ? C16 C17 C18 121.5(3) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 119.3 . . ? C19 C18 C17 121.1(3) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 117.4(2) . . ? C18 C19 C22 121.6(3) . . ? C20 C19 C22 121.0(3) . . ? C19 C20 C21 121.7(3) . . ? C19 C20 H20A 119.1 . . ? C21 C20 H20A 119.1 . . ? C20 C21 C16 120.6(2) . . ? C20 C21 H21A 119.7 . . ? C16 C21 H21A 119.7 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C32 N31 C39 129.3(3) . . ? C32 N31 H31N 113(2) . . ? C39 N31 H31N 115(2) . . ? N32 C32 N31 120.6(3) . . ? N32 C32 C33 125.5(3) . . ? N31 C32 C33 113.9(3) . . ? C32 N32 C46 116.8(2) . . ? C34 C33 C38 118.6(3) . . ? C34 C33 C32 123.4(3) . . ? C38 C33 C32 118.0(2) . . ? C35 C34 C33 121.6(3) . . ? C35 C34 H34A 119.2 . . ? C33 C34 H34A 119.2 . . ? C36 C35 C34 119.5(3) . . ? C36 C35 H35A 120.3 . . ? C34 C35 H35A 120.3 . . ? C37 C36 C35 121.8(3) . . ? C37 C36 H36A 119.1 . . ? C35 C36 H36A 119.1 . . ? C36 C37 C38 118.8(3) . . ? C36 C37 H37A 120.6 . . ? C38 C37 H37A 120.6 . . ? C33 C38 C37 119.7(3) . . ? C33 C38 H38A 120.1 . . ? C37 C38 H38A 120.1 . . ? C40 C39 C44 118.2(2) . . ? C40 C39 N31 125.8(2) . . ? C44 C39 N31 115.9(2) . . ? C41 C40 C39 120.3(3) . . ? C41 C40 H40A 119.8 . . ? C39 C40 H40A 119.8 . . ? C42 C41 C40 122.3(3) . . ? C42 C41 H41A 118.9 . . ? C40 C41 H41A 118.9 . . ? C41 C42 C43 118.0(3) . . ? C41 C42 C45 121.0(3) . . ? C43 C42 C45 121.0(3) . . ? C42 C43 C44 121.1(3) . . ? C42 C43 H43A 119.4 . . ? C44 C43 H43A 119.4 . . ? C39 C44 C43 120.0(3) . . ? C39 C44 H44A 120.0 . . ? C43 C44 H44A 120.0 . . ? C42 C45 H45A 109.5 . . ? C42 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C42 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C47 C46 C51 118.3(2) . . ? C47 C46 N32 121.3(2) . . ? C51 C46 N32 120.2(2) . . ? C48 C47 C46 120.6(3) . . ? C48 C47 H47A 119.7 . . ? C46 C47 H47A 119.7 . . ? C47 C48 C49 122.0(3) . . ? C47 C48 H48A 119.0 . . ? C49 C48 H48A 119.0 . . ? C48 C49 C50 117.3(3) . . ? C48 C49 C52 121.3(3) . . ? C50 C49 C52 121.4(3) . . ? C49 C50 C51 122.1(3) . . ? C49 C50 H50A 119.0 . . ? C51 C50 H50A 119.0 . . ? C50 C51 C46 119.7(3) . . ? C50 C51 H51A 120.1 . . ? C46 C51 H51A 120.1 . . ? C49 C52 H52A 109.5 . . ? C49 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C49 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 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 C9 N1 C2 N2 7.6(4) . . . . ? C9 N1 C2 C3 -175.4(2) . . . . ? N1 C2 N2 C16 -172.3(2) . . . . ? C3 C2 N2 C16 11.1(4) . . . . ? N2 C2 C3 C4 -130.3(3) . . . . ? N1 C2 C3 C4 52.8(3) . . . . ? N2 C2 C3 C8 50.3(4) . . . . ? N1 C2 C3 C8 -126.6(3) . . . . ? C8 C3 C4 C5 -1.4(4) . . . . ? C2 C3 C4 C5 179.2(2) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C7 0.8(5) . . . . ? C5 C6 C7 C8 -1.1(5) . . . . ? C6 C7 C8 C3 0.1(5) . . . . ? C4 C3 C8 C7 1.1(4) . . . . ? C2 C3 C8 C7 -179.4(3) . . . . ? C2 N1 C9 C14 -154.1(3) . . . . ? C2 N1 C9 C10 29.2(4) . . . . ? C14 C9 C10 C11 -1.0(4) . . . . ? N1 C9 C10 C11 175.6(3) . . . . ? C9 C10 C11 C12 -0.1(5) . . . . ? C10 C11 C12 C13 0.9(5) . . . . ? C10 C11 C12 C15 -179.1(3) . . . . ? C11 C12 C13 C14 -0.6(5) . . . . ? C15 C12 C13 C14 179.4(3) . . . . ? C10 C9 C14 C13 1.2(4) . . . . ? N1 C9 C14 C13 -175.6(2) . . . . ? C12 C13 C14 C9 -0.4(4) . . . . ? C2 N2 C16 C17 64.4(3) . . . . ? C2 N2 C16 C21 -120.4(3) . . . . ? C21 C16 C17 C18 2.4(4) . . . . ? N2 C16 C17 C18 177.8(3) . . . . ? C16 C17 C18 C19 -0.4(5) . . . . ? C17 C18 C19 C20 -0.7(4) . . . . ? C17 C18 C19 C22 179.3(3) . . . . ? C18 C19 C20 C21 -0.3(4) . . . . ? C22 C19 C20 C21 179.7(3) . . . . ? C19 C20 C21 C16 2.3(4) . . . . ? C17 C16 C21 C20 -3.3(4) . . . . ? N2 C16 C21 C20 -178.7(2) . . . . ? C39 N31 C32 N32 -13.8(4) . . . . ? C39 N31 C32 C33 168.4(2) . . . . ? N31 C32 N32 C46 166.8(2) . . . . ? C33 C32 N32 C46 -15.7(4) . . . . ? N32 C32 C33 C34 128.4(3) . . . . ? N31 C32 C33 C34 -54.0(4) . . . . ? N32 C32 C33 C38 -49.9(4) . . . . ? N31 C32 C33 C38 127.8(3) . . . . ? C38 C33 C34 C35 1.9(4) . . . . ? C32 C33 C34 C35 -176.4(3) . . . . ? C33 C34 C35 C36 -0.1(4) . . . . ? C34 C35 C36 C37 -1.4(5) . . . . ? C35 C36 C37 C38 1.0(5) . . . . ? C34 C33 C38 C37 -2.2(4) . . . . ? C32 C33 C38 C37 176.2(3) . . . . ? C36 C37 C38 C33 0.8(4) . . . . ? C32 N31 C39 C40 -8.8(4) . . . . ? C32 N31 C39 C44 174.1(3) . . . . ? C44 C39 C40 C41 0.9(4) . . . . ? N31 C39 C40 C41 -176.2(2) . . . . ? C39 C40 C41 C42 0.8(4) . . . . ? C40 C41 C42 C43 -1.0(4) . . . . ? C40 C41 C42 C45 179.8(3) . . . . ? C41 C42 C43 C44 -0.6(4) . . . . ? C45 C42 C43 C44 178.6(3) . . . . ? C40 C39 C44 C43 -2.4(4) . . . . ? N31 C39 C44 C43 174.9(2) . . . . ? C42 C43 C44 C39 2.3(4) . . . . ? C32 N32 C46 C47 -65.0(4) . . . . ? C32 N32 C46 C51 119.4(3) . . . . ? C51 C46 C47 C48 -1.8(4) . . . . ? N32 C46 C47 C48 -177.5(3) . . . . ? C46 C47 C48 C49 0.0(4) . . . . ? C47 C48 C49 C50 1.5(4) . . . . ? C47 C48 C49 C52 -179.1(3) . . . . ? C48 C49 C50 C51 -1.3(4) . . . . ? C52 C49 C50 C51 179.3(3) . . . . ? C49 C50 C51 C46 -0.5(5) . . . . ? C47 C46 C51 C50 2.0(4) . . . . ? N32 C46 C51 C50 177.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N N32 0.964(17) 2.062(18) 3.020(3) 172(2) . N31 H31N N2 0.981(18) 2.32(3) 3.145(3) 141(3) 3_546 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.351 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.045