# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_rn101c #TrackingRef 'RN-85.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 Br N4' _chemical_formula_sum 'C18 H13 Br N4' _chemical_formula_weight 365.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5297(8) _cell_length_b 15.7552(16) _cell_length_c 12.3971(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.664(10) _cell_angle_gamma 90.00 _cell_volume 1465.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 470 _cell_measurement_theta_min 3.0005 _cell_measurement_theta_max 28.8635 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.809 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.07869 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3007 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.1015 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2035 _reflns_number_gt 1160 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _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^)+(0.0065P)^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_number_reflns 2035 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1224 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0654 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.007 _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 Br1 Br 0.31618(9) 0.42634(4) -0.01921(7) 0.0585(3) Uani 1 1 d . . . N1 N 0.2026(6) 0.0588(3) -0.0810(5) 0.0336(14) Uani 1 1 d . . . N2 N 0.3248(6) 0.0967(4) 0.0833(4) 0.0438(15) Uani 1 1 d . . . H2 H 0.3685 0.0941 0.1495 0.053 Uiso 1 1 calc R . . N3 N 0.2007(6) -0.1095(3) -0.0345(5) 0.0386(14) Uani 1 1 d . . . C4 C 0.2141(8) 0.2809(5) -0.1401(6) 0.0495(19) Uani 1 1 d . . . H4 H 0.1907 0.3209 -0.1944 0.059 Uiso 1 1 calc R . . C5 C 0.2976(7) -0.1890(4) 0.1090(6) 0.0359(17) Uani 1 1 d . . . C6 C 0.3270(7) -0.2654(4) 0.1637(6) 0.048(2) Uani 1 1 d . . . H6 H 0.3823 -0.2660 0.2336 0.057 Uiso 1 1 calc R . . C7 C 0.1898(8) -0.3410(4) 0.0108(6) 0.051(2) Uani 1 1 d . . . H7 H 0.1541 -0.3929 -0.0196 0.061 Uiso 1 1 calc R . . N8 N 0.1806(6) 0.1986(4) -0.1635(5) 0.0465(15) Uani 1 1 d . . . C9 C 0.2127(7) -0.1927(4) 0.0032(6) 0.0403(18) Uani 1 1 d . . . C10 C 0.2958(7) 0.1686(4) 0.0210(6) 0.0375(18) Uani 1 1 d . . . C11 C 0.1571(7) -0.2679(4) -0.0487(6) 0.051(2) Uani 1 1 d . . . H11 H 0.1018 -0.2686 -0.1186 0.062 Uiso 1 1 calc R . . C12 C 0.1273(7) 0.0019(4) -0.1604(6) 0.0364(17) Uani 1 1 d . . . C13 C 0.2712(7) 0.0324(4) 0.0199(6) 0.0382(19) Uani 1 1 d . . . C14 C 0.3365(7) -0.1021(4) 0.1355(6) 0.0351(17) Uani 1 1 d . . . C15 C 0.2814(8) 0.3084(4) -0.0395(6) 0.0424(18) Uani 1 1 d . . . C16 C 0.2743(8) -0.3395(4) 0.1143(7) 0.053(2) Uani 1 1 d . . . H16 H 0.2955 -0.3905 0.1510 0.064 Uiso 1 1 calc R . . C17 C 0.2221(7) 0.1466(4) -0.0823(6) 0.0353(17) Uani 1 1 d . . . C19 C 0.4282(7) -0.0714(4) 0.2380(5) 0.0517(19) Uani 1 1 d . . . H19A H 0.3674 -0.0922 0.2978 0.078 Uiso 1 1 calc R . . H19B H 0.4279 -0.0104 0.2386 0.078 Uiso 1 1 calc R . . H19C H 0.5489 -0.0915 0.2441 0.078 Uiso 1 1 calc R . . C20 C 0.3257(7) 0.2545(4) 0.0447(6) 0.0442(19) Uani 1 1 d . . . H20 H 0.3719 0.2734 0.1124 0.053 Uiso 1 1 calc R . . C21 C 0.1287(7) -0.0802(4) -0.1321(6) 0.0398(17) Uani 1 1 d . . . H21 H 0.0779 -0.1193 -0.1816 0.048 Uiso 1 1 calc R . . C23 C 0.2756(7) -0.0560(4) 0.0470(6) 0.0394(18) Uani 1 1 d . . . C24 C 0.0516(7) 0.0368(4) -0.2644(5) 0.052(2) Uani 1 1 d . . . H24A H -0.0396 0.0773 -0.2516 0.078 Uiso 1 1 calc R . . H24B H 0.0011 -0.0084 -0.3089 0.078 Uiso 1 1 calc R . . H24C H 0.1439 0.0642 -0.3006 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 Br1 0.0730(5) 0.0440(5) 0.0579(6) 0.0013(4) 0.0015(4) 0.0021(4) N1 0.036(3) 0.039(4) 0.026(4) 0.000(3) 0.003(3) -0.002(2) N2 0.050(3) 0.065(4) 0.015(4) 0.001(3) -0.009(3) 0.006(3) N3 0.042(3) 0.043(4) 0.030(4) -0.005(3) -0.003(3) -0.006(3) C4 0.052(4) 0.056(5) 0.041(6) 0.013(4) 0.005(4) 0.016(4) C5 0.036(3) 0.044(5) 0.027(5) -0.001(4) 0.003(3) -0.001(3) C6 0.048(4) 0.049(5) 0.048(6) 0.002(4) 0.016(4) 0.001(3) C7 0.059(4) 0.039(5) 0.056(6) -0.010(4) 0.007(4) -0.001(3) N8 0.048(3) 0.050(4) 0.039(5) 0.007(4) -0.008(3) 0.014(3) C9 0.043(4) 0.040(5) 0.039(6) -0.004(4) 0.011(4) -0.001(3) C10 0.039(4) 0.046(5) 0.028(5) -0.002(4) 0.002(4) 0.006(3) C11 0.048(4) 0.051(5) 0.055(6) -0.007(5) 0.005(4) -0.004(3) C12 0.033(3) 0.050(5) 0.025(5) -0.010(4) -0.003(3) 0.000(3) C13 0.033(4) 0.049(5) 0.033(6) -0.016(4) 0.006(4) -0.003(3) C14 0.034(3) 0.046(5) 0.026(5) -0.003(4) 0.006(3) -0.003(3) C15 0.050(4) 0.045(5) 0.031(5) 0.002(4) -0.002(4) 0.008(3) C16 0.055(4) 0.040(5) 0.066(7) 0.008(4) 0.014(5) 0.005(3) C17 0.032(3) 0.034(5) 0.039(6) -0.003(4) -0.002(3) 0.006(3) C19 0.053(4) 0.060(5) 0.041(5) -0.003(4) -0.002(4) -0.005(3) C20 0.043(4) 0.050(5) 0.040(6) -0.017(4) 0.001(4) -0.002(3) C21 0.038(4) 0.045(5) 0.035(5) -0.011(4) -0.004(3) -0.002(3) C23 0.034(4) 0.048(5) 0.036(5) -0.007(4) 0.001(4) -0.007(3) C24 0.052(4) 0.066(6) 0.035(6) -0.014(4) -0.007(4) -0.007(3) _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 Br1 C15 1.891(6) . ? N1 C13 1.378(8) . ? N1 C17 1.391(7) . ? N1 C12 1.415(8) . ? N2 C13 1.324(7) . ? N2 C10 1.379(8) . ? N2 H2 0.8600 . ? N3 C21 1.366(7) . ? N3 C9 1.391(7) . ? N3 C23 1.398(8) . ? C4 N8 1.348(8) . ? C4 C15 1.377(9) . ? C4 H4 0.9300 . ? C5 C6 1.391(8) . ? C5 C9 1.413(9) . ? C5 C14 1.433(8) . ? C6 C16 1.363(8) . ? C6 H6 0.9300 . ? C7 C11 1.379(8) . ? C7 C16 1.386(9) . ? C7 H7 0.9300 . ? N8 C17 1.315(7) . ? C9 C11 1.396(8) . ? C10 C17 1.397(9) . ? C10 C20 1.399(8) . ? C11 H11 0.9300 . ? C12 C21 1.340(8) . ? C12 C24 1.474(8) . ? C13 C23 1.433(8) . ? C14 C23 1.364(9) . ? C14 C19 1.477(8) . ? C15 C20 1.366(8) . ? C16 H16 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 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 C13 N1 C17 106.2(5) . . ? C13 N1 C12 122.6(6) . . ? C17 N1 C12 131.2(6) . . ? C13 N2 C10 105.6(7) . . ? C13 N2 H2 127.2 . . ? C10 N2 H2 127.2 . . ? C21 N3 C9 128.8(6) . . ? C21 N3 C23 122.9(6) . . ? C9 N3 C23 108.3(6) . . ? N8 C4 C15 123.2(7) . . ? N8 C4 H4 118.4 . . ? C15 C4 H4 118.4 . . ? C6 C5 C9 117.3(7) . . ? C6 C5 C14 134.0(7) . . ? C9 C5 C14 108.7(6) . . ? C16 C6 C5 119.6(8) . . ? C16 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C11 C7 C16 122.0(7) . . ? C11 C7 H7 119.0 . . ? C16 C7 H7 119.0 . . ? C17 N8 C4 113.9(6) . . ? N3 C9 C11 129.5(8) . . ? N3 C9 C5 106.5(6) . . ? C11 C9 C5 124.0(7) . . ? N2 C10 C17 110.0(6) . . ? N2 C10 C20 131.5(7) . . ? C17 C10 C20 118.6(6) . . ? C7 C11 C9 115.4(8) . . ? C7 C11 H11 122.3 . . ? C9 C11 H11 122.3 . . ? C21 C12 N1 115.8(6) . . ? C21 C12 C24 125.7(6) . . ? N1 C12 C24 118.5(6) . . ? N2 C13 N1 112.4(7) . . ? N2 C13 C23 127.2(8) . . ? N1 C13 C23 120.4(6) . . ? C23 C14 C5 106.0(6) . . ? C23 C14 C19 128.4(6) . . ? C5 C14 C19 125.7(6) . . ? C20 C15 C4 123.0(7) . . ? C20 C15 Br1 119.1(6) . . ? C4 C15 Br1 117.9(6) . . ? C6 C16 C7 121.7(7) . . ? C6 C16 H16 119.1 . . ? C7 C16 H16 119.1 . . ? N8 C17 N1 127.5(7) . . ? N8 C17 C10 126.8(6) . . ? N1 C17 C10 105.7(6) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 C10 114.5(7) . . ? C15 C20 H20 122.7 . . ? C10 C20 H20 122.7 . . ? C12 C21 N3 123.6(6) . . ? C12 C21 H21 118.2 . . ? N3 C21 H21 118.2 . . ? C14 C23 N3 110.5(6) . . ? C14 C23 C13 134.9(7) . . ? N3 C23 C13 114.7(7) . . ? C12 C24 H24A 109.5 . . ? C12 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C12 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.676 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.676 _refine_diff_density_max 0.396 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 921987' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_521 #TrackingRef 'RN-86.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H17 N3' _chemical_formula_sum 'C23 H17 N3' _chemical_formula_weight 335.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.928(2) _cell_length_b 16.966(5) _cell_length_c 12.302(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.429(5) _cell_angle_gamma 90.00 _cell_volume 1651.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 9756 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.05 _exptl_crystal_description NEEDLE _exptl_crystal_colour WINERED _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9824 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16856 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.12 _reflns_number_total 3268 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.2640P] 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 3268 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C22 C 0.3240(2) 0.38863(9) 0.31312(13) 0.0598(4) Uani 1 1 d . . . H22A H 0.3285 0.3714 0.2390 0.090 Uiso 1 1 calc R . . H22B H 0.2602 0.3515 0.3528 0.090 Uiso 1 1 calc R . . H22C H 0.4366 0.3923 0.3460 0.090 Uiso 1 1 calc R . . N3 N 0.22095(12) 0.50451(6) 0.41559(8) 0.0415(3) Uani 1 1 d . . . N2 N 0.10182(13) 0.57621(6) 0.22936(9) 0.0444(3) Uani 1 1 d . . . C10 C 0.27232(15) 0.48262(8) 0.52222(10) 0.0436(3) Uani 1 1 d . . . N1 N 0.12131(14) 0.59937(7) 0.52484(9) 0.0483(3) Uani 1 1 d . . . C8 C 0.39409(16) 0.41769(8) 0.68018(11) 0.0478(3) Uani 1 1 d . . . C21 C 0.03454(16) 0.62133(8) 0.14495(11) 0.0455(3) Uani 1 1 d . . . C1 C 0.20707(16) 0.54263(8) 0.58820(11) 0.0463(3) Uani 1 1 d . . . C3 C 0.32786(17) 0.47725(9) 0.74744(11) 0.0499(3) Uani 1 1 d . . . C13 C 0.06918(16) 0.61324(7) 0.32744(11) 0.0434(3) Uani 1 1 d . . . C17 C -0.12799(18) 0.74093(8) 0.12074(13) 0.0533(4) Uani 1 1 d . . . H17 H -0.1834 0.7840 0.1487 0.064 Uiso 1 1 calc R . . C14 C 0.13300(16) 0.57524(7) 0.42494(11) 0.0436(3) Uani 1 1 d . . . C2 C 0.23409(17) 0.53957(9) 0.69962(11) 0.0513(4) Uani 1 1 d . . . H2 H 0.1904 0.5786 0.7430 0.062 Uiso 1 1 calc R . . C15 C -0.01991(16) 0.68152(8) 0.30641(11) 0.0463(3) Uani 1 1 d . . . C12 C 0.18294(16) 0.50428(8) 0.22541(11) 0.0461(3) Uani 1 1 d . . . H12 H 0.1972 0.4811 0.1581 0.055 Uiso 1 1 calc R . . C11 C 0.24128(16) 0.46728(8) 0.31542(11) 0.0445(3) Uani 1 1 d . . . C16 C -0.04370(16) 0.68705(8) 0.19088(12) 0.0467(3) Uani 1 1 d . . . C9 C 0.36533(17) 0.42134(8) 0.56633(11) 0.0476(3) Uani 1 1 d . . . H9 H 0.4087 0.3829 0.5219 0.057 Uiso 1 1 calc R . . C4 C 0.3605(2) 0.47033(11) 0.86182(12) 0.0605(4) Uani 1 1 d . . . H4 H 0.3190 0.5087 0.9072 0.073 Uiso 1 1 calc R . . C20 C 0.03664(19) 0.61026(9) 0.03307(12) 0.0539(4) Uani 1 1 d . . . H20 H 0.0909 0.5672 0.0040 0.065 Uiso 1 1 calc R . . C7 C 0.48775(18) 0.35515(10) 0.73057(12) 0.0564(4) Uani 1 1 d . . . H7 H 0.5315 0.3160 0.6875 0.068 Uiso 1 1 calc R . . C5 C 0.4502(2) 0.40946(11) 0.90652(13) 0.0660(5) Uani 1 1 d . . . H5 H 0.4690 0.4064 0.9818 0.079 Uiso 1 1 calc R . . C6 C 0.5149(2) 0.35122(11) 0.84043(13) 0.0642(4) Uani 1 1 d . . . H6 H 0.5769 0.3096 0.8718 0.077 Uiso 1 1 calc R . . C18 C -0.12808(19) 0.72962(9) 0.01078(13) 0.0582(4) Uani 1 1 d . . . H18 H -0.1847 0.7652 -0.0359 0.070 Uiso 1 1 calc R . . C23 C -0.0822(2) 0.73869(9) 0.38679(14) 0.0608(4) Uani 1 1 d . . . H23A H -0.0565 0.7194 0.4592 0.091 Uiso 1 1 calc R . . H23B H -0.2023 0.7448 0.3748 0.091 Uiso 1 1 calc R . . H23C H -0.0281 0.7887 0.3781 0.091 Uiso 1 1 calc R . . C19 C -0.0445(2) 0.66542(9) -0.03286(13) 0.0593(4) Uani 1 1 d . . . H19 H -0.0439 0.6600 -0.1081 0.071 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 C22 0.0711(10) 0.0526(9) 0.0550(9) -0.0062(7) -0.0005(7) 0.0157(7) N3 0.0400(6) 0.0402(6) 0.0443(6) -0.0025(4) 0.0024(4) -0.0027(4) N2 0.0436(6) 0.0416(6) 0.0478(6) -0.0008(5) 0.0031(5) 0.0002(5) C10 0.0396(6) 0.0470(7) 0.0443(7) -0.0018(6) 0.0039(5) -0.0091(5) N1 0.0474(6) 0.0457(6) 0.0519(7) -0.0083(5) 0.0029(5) -0.0045(5) C8 0.0428(7) 0.0542(8) 0.0465(7) 0.0012(6) 0.0032(5) -0.0104(6) C21 0.0415(7) 0.0425(7) 0.0524(8) 0.0024(6) 0.0025(5) -0.0040(5) C1 0.0411(7) 0.0486(8) 0.0493(7) -0.0056(6) 0.0032(6) -0.0108(6) C3 0.0437(7) 0.0594(8) 0.0466(7) -0.0029(6) 0.0034(6) -0.0145(6) C13 0.0396(6) 0.0402(7) 0.0505(7) -0.0058(5) 0.0033(5) -0.0053(5) C17 0.0505(8) 0.0396(7) 0.0696(10) 0.0025(6) 0.0017(7) -0.0023(6) C14 0.0384(6) 0.0408(7) 0.0515(7) -0.0046(6) 0.0033(5) -0.0062(5) C2 0.0492(8) 0.0568(8) 0.0485(8) -0.0110(6) 0.0067(6) -0.0098(6) C15 0.0422(7) 0.0399(7) 0.0567(8) -0.0050(6) 0.0015(6) -0.0045(5) C12 0.0457(7) 0.0455(7) 0.0474(7) -0.0061(6) 0.0046(6) 0.0018(6) C11 0.0424(7) 0.0440(7) 0.0472(7) -0.0042(6) 0.0038(5) -0.0005(5) C16 0.0421(7) 0.0392(7) 0.0587(8) -0.0011(6) 0.0020(6) -0.0066(5) C9 0.0462(7) 0.0494(8) 0.0473(7) -0.0004(6) 0.0038(6) -0.0036(6) C4 0.0585(9) 0.0769(11) 0.0463(8) -0.0058(7) 0.0045(7) -0.0141(8) C20 0.0564(8) 0.0516(8) 0.0540(8) 0.0008(6) 0.0065(6) 0.0015(6) C7 0.0537(8) 0.0623(9) 0.0531(8) 0.0058(7) 0.0018(6) -0.0045(7) C5 0.0676(10) 0.0856(12) 0.0442(8) 0.0061(8) -0.0029(7) -0.0170(9) C6 0.0618(9) 0.0743(11) 0.0557(9) 0.0129(8) -0.0038(7) -0.0091(8) C18 0.0568(8) 0.0512(8) 0.0658(9) 0.0130(7) -0.0027(7) -0.0020(7) C23 0.0654(9) 0.0471(8) 0.0697(10) -0.0120(7) 0.0027(8) 0.0037(7) C19 0.0643(9) 0.0605(9) 0.0529(8) 0.0084(7) 0.0025(7) -0.0027(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 C22 C11 1.4878(19) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? N3 C14 1.3961(17) . ? N3 C10 1.4003(17) . ? N3 C11 1.4025(17) . ? N2 C21 1.3721(17) . ? N2 C12 1.3817(17) . ? N2 C13 1.3982(17) . ? C10 C9 1.368(2) . ? C10 C1 1.4190(19) . ? N1 C14 1.3039(17) . ? N1 C1 1.3902(18) . ? C8 C9 1.407(2) . ? C8 C7 1.416(2) . ? C8 C3 1.426(2) . ? C21 C20 1.390(2) . ? C21 C16 1.4104(19) . ? C1 C2 1.376(2) . ? C3 C2 1.402(2) . ? C3 C4 1.420(2) . ? C13 C15 1.3733(19) . ? C13 C14 1.4274(19) . ? C17 C18 1.366(2) . ? C17 C16 1.399(2) . ? C17 H17 0.9300 . ? C2 H2 0.9300 . ? C15 C16 1.426(2) . ? C15 C23 1.490(2) . ? C12 C11 1.3314(19) . ? C12 H12 0.9300 . ? C9 H9 0.9300 . ? C4 C5 1.352(2) . ? C4 H4 0.9300 . ? C20 C19 1.373(2) . ? C20 H20 0.9300 . ? C7 C6 1.357(2) . ? C7 H7 0.9300 . ? C5 C6 1.397(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C18 C19 1.399(2) . ? C18 H18 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C19 H19 0.9300 . ? 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 C11 C22 H22A 109.5 . . ? C11 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C11 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C14 N3 C10 105.64(10) . . ? C14 N3 C11 122.94(11) . . ? C10 N3 C11 131.40(11) . . ? C21 N2 C12 128.82(12) . . ? C21 N2 C13 108.59(11) . . ? C12 N2 C13 122.53(11) . . ? C9 C10 N3 133.86(12) . . ? C9 C10 C1 121.66(13) . . ? N3 C10 C1 104.47(11) . . ? C14 N1 C1 104.54(11) . . ? C9 C8 C7 121.21(13) . . ? C9 C8 C3 120.20(13) . . ? C7 C8 C3 118.59(13) . . ? N2 C21 C20 130.30(13) . . ? N2 C21 C16 107.35(12) . . ? C20 C21 C16 122.35(13) . . ? C2 C1 N1 128.80(13) . . ? C2 C1 C10 120.16(13) . . ? N1 C1 C10 111.04(12) . . ? C2 C3 C4 122.60(14) . . ? C2 C3 C8 119.71(13) . . ? C4 C3 C8 117.69(14) . . ? C15 C13 N2 109.64(12) . . ? C15 C13 C14 133.77(13) . . ? N2 C13 C14 116.59(12) . . ? C18 C17 C16 119.39(14) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? N1 C14 N3 114.30(12) . . ? N1 C14 C13 127.48(12) . . ? N3 C14 C13 118.21(11) . . ? C1 C2 C3 119.60(13) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C13 C15 C16 106.21(12) . . ? C13 C15 C23 127.68(14) . . ? C16 C15 C23 126.10(13) . . ? C11 C12 N2 121.77(12) . . ? C11 C12 H12 119.1 . . ? N2 C12 H12 119.1 . . ? C12 C11 N3 117.77(12) . . ? C12 C11 C22 122.59(13) . . ? N3 C11 C22 119.64(12) . . ? C17 C16 C21 118.34(13) . . ? C17 C16 C15 133.44(13) . . ? C21 C16 C15 108.20(12) . . ? C10 C9 C8 118.68(13) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C5 C4 C3 121.75(15) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C19 C20 C21 117.38(14) . . ? C19 C20 H20 121.3 . . ? C21 C20 H20 121.3 . . ? C6 C7 C8 121.35(16) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C4 C5 C6 120.42(15) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 120.19(16) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C17 C18 C19 121.14(14) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C15 C23 H23A 109.5 . . ? C15 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C15 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C19 C18 121.34(15) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.12 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.213 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 921988' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_rn113-2m #TrackingRef 'RN-87.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H34 N6 O' _chemical_formula_sum 'C40 H34 N6 O' _chemical_formula_weight 614.73 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.482(3) _cell_length_b 24.976(4) _cell_length_c 14.268(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.136(2) _cell_angle_gamma 90.00 _cell_volume 6259.1(17) _cell_formula_units_Z 8 _cell_measurement_temperature 298 _cell_measurement_reflns_used 9344 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.75 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9809 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32322 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 26.04 _reflns_number_total 6180 _reflns_number_gt 3918 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 6180 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1411 _refine_ls_R_factor_gt 0.1048 _refine_ls_wR_factor_ref 0.3499 _refine_ls_wR_factor_gt 0.3198 _refine_ls_goodness_of_fit_ref 1.301 _refine_ls_restrained_S_all 1.301 _refine_ls_shift/su_max 0.262 _refine_ls_shift/su_mean 0.010 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 0.09715(15) 0.08767(11) 0.87778(19) 0.0507(7) Uani 1 1 d . . . C1 C 0.02082(19) 0.08907(15) 0.8761(2) 0.0518(9) Uani 1 1 d . . . C2 C -0.01501(19) 0.03846(15) 0.8749(2) 0.0514(9) Uani 1 1 d . . . C3 C 0.1222(2) 0.13946(15) 0.8780(2) 0.0572(9) Uani 1 1 d . . . N2 N 0.02816(18) -0.00826(12) 0.87813(18) 0.0555(8) Uani 1 1 d . . . C4 C -0.0217(2) -0.05133(17) 0.8742(2) 0.0641(11) Uani 1 1 d . . . N3 N -0.08620(17) 0.02819(14) 0.8697(2) 0.0638(9) Uani 1 1 d . . . C5 C 0.13763(19) 0.04083(15) 0.8851(2) 0.0553(9) Uani 1 1 d . . . H5 H 0.1888 0.0424 0.8892 0.066 Uiso 1 1 calc R . . C6 C 0.1933(2) 0.15870(16) 0.8794(3) 0.0657(10) Uani 1 1 d . . . H6 H 0.2329 0.1357 0.8800 0.079 Uiso 1 1 calc R . . C7 C -0.00238(18) 0.14097(15) 0.8762(2) 0.0531(9) Uani 1 1 d . . . C8 C 0.1052(2) -0.00681(15) 0.8864(2) 0.0552(9) Uani 1 1 d . . . C9 C 0.0609(2) 0.17299(15) 0.8770(2) 0.0578(9) Uani 1 1 d . . . C10 C -0.0909(2) -0.02788(18) 0.8701(2) 0.0678(11) Uani 1 1 d . . . C11 C -0.1536(3) -0.0606(2) 0.8651(3) 0.0814(13) Uani 1 1 d . . . H11 H -0.2004 -0.0457 0.8621 0.098 Uiso 1 1 calc R . . C12 C 0.1484(3) -0.05792(18) 0.8992(3) 0.0800(12) Uani 1 1 d . . . H12A H 0.1275 -0.0801 0.8423 0.120 Uiso 1 1 calc R . . H12B H 0.1447 -0.0761 0.9568 0.120 Uiso 1 1 calc R . . H12C H 0.2008 -0.0505 0.9068 0.120 Uiso 1 1 calc R . . C13 C 0.0721(3) 0.22842(18) 0.8753(3) 0.0765(12) Uani 1 1 d . . . H13 H 0.0328 0.2521 0.8731 0.092 Uiso 1 1 calc R . . C14 C 0.1430(3) 0.24714(19) 0.8769(3) 0.0850(13) Uani 1 1 d . . . H14 H 0.1509 0.2839 0.8759 0.102 Uiso 1 1 calc R . . C15 C -0.1443(4) -0.1153(2) 0.8646(3) 0.0953(18) Uani 1 1 d . . . C16 C -0.0766(3) -0.1368(2) 0.8680(3) 0.0884(15) Uani 1 1 d . . . H16 H -0.0724 -0.1739 0.8673 0.106 Uiso 1 1 calc R . . C17 C -0.0787(2) 0.16068(18) 0.8773(3) 0.0708(11) Uani 1 1 d . . . H17A H -0.1071 0.1315 0.8921 0.106 Uiso 1 1 calc R . . H17B H -0.1059 0.1753 0.8138 0.106 Uiso 1 1 calc R . . H17C H -0.0719 0.1880 0.9267 0.106 Uiso 1 1 calc R . . C18 C -0.0135(3) -0.10672(18) 0.8725(3) 0.0827(14) Uani 1 1 d . . . H18 H 0.0325 -0.1225 0.8743 0.099 Uiso 1 1 calc R . . C19 C 0.2019(3) 0.21318(19) 0.8798(3) 0.0819(13) Uani 1 1 d . . . H19 H 0.2489 0.2275 0.8822 0.098 Uiso 1 1 calc R . . N4 N 1.03552(16) 0.47720(12) 0.12674(18) 0.0525(7) Uani 1 1 d . . . C20 C 0.95875(19) 0.47819(16) 0.1210(2) 0.0529(9) Uani 1 1 d . . . N6 N 0.85210(17) 0.41673(16) 0.1194(2) 0.0690(10) Uani 1 1 d . . . C21 C 0.92292(19) 0.42789(15) 0.1197(2) 0.0533(9) Uani 1 1 d . . . C22 C 0.9158(2) 0.33829(18) 0.1201(2) 0.0644(11) Uani 1 1 d . . . N5 N 0.96480(17) 0.38155(13) 0.12003(18) 0.0566(8) Uani 1 1 d . . . C23 C 1.0610(2) 0.52894(15) 0.1291(2) 0.0548(9) Uani 1 1 d . . . C24 C 0.9988(2) 0.56220(15) 0.1247(2) 0.0564(9) Uani 1 1 d . . . C25 C 0.8477(2) 0.36122(18) 0.1201(2) 0.0635(10) Uani 1 1 d . . . C26 C 0.7868(3) 0.3291(2) 0.1229(3) 0.0783(13) Uani 1 1 d . . . H26 H 0.7409 0.3441 0.1237 0.094 Uiso 1 1 calc R . . C27 C 1.1323(2) 0.54806(17) 0.1335(3) 0.0653(10) Uani 1 1 d . . . H27 H 1.1720 0.5247 0.1357 0.078 Uiso 1 1 calc R . . C28 C 1.04164(19) 0.38223(15) 0.1231(2) 0.0542(9) Uani 1 1 d . . . C29 C 0.93458(19) 0.53048(16) 0.1188(2) 0.0562(9) Uani 1 1 d . . . C30 C 1.0819(2) 0.33170(17) 0.1209(3) 0.0730(11) Uani 1 1 d . . . H30A H 1.1320 0.3393 0.1175 0.110 Uiso 1 1 calc R . . H30B H 1.0541 0.3112 0.0641 0.110 Uiso 1 1 calc R . . H30C H 1.0860 0.3116 0.1796 0.110 Uiso 1 1 calc R . . C31 C 1.1427(2) 0.60221(18) 0.1346(3) 0.0725(11) Uani 1 1 d . . . H31 H 1.1898 0.6162 0.1363 0.087 Uiso 1 1 calc R . . C32 C 1.07461(19) 0.43068(16) 0.1272(2) 0.0555(9) Uani 1 1 d . . . H32 H 1.1256 0.4325 0.1305 0.067 Uiso 1 1 calc R . . C33 C 0.7968(3) 0.2741(2) 0.1246(3) 0.0881(15) Uani 1 1 d . . . C34 C 0.8557(2) 0.54941(19) 0.1083(3) 0.0742(12) Uani 1 1 d . . . H34A H 0.8214 0.5195 0.0938 0.111 Uiso 1 1 calc R . . H34B H 0.8401 0.5750 0.0556 0.111 Uiso 1 1 calc R . . H34C H 0.8549 0.5659 0.1688 0.111 Uiso 1 1 calc R . . C35 C 1.0823(3) 0.6369(2) 0.1331(3) 0.0882(14) Uani 1 1 d . . . H35 H 1.0907 0.6737 0.1356 0.106 Uiso 1 1 calc R . . C36 C 0.9240(3) 0.28307(19) 0.1206(3) 0.0810(13) Uani 1 1 d . . . H36 H 0.9693 0.2673 0.1195 0.097 Uiso 1 1 calc R . . C37 C 1.0112(2) 0.61786(19) 0.1282(3) 0.0709(11) Uani 1 1 d . . . H37 H 0.9720 0.6414 0.1271 0.085 Uiso 1 1 calc R . . C38 C 0.8627(3) 0.2526(2) 0.1228(3) 0.0855(14) Uani 1 1 d . . . H38 H 0.8672 0.2155 0.1231 0.103 Uiso 1 1 calc R . . O2 O 0.25354(15) 0.44315(14) 0.26298(19) 0.0896(10) Uani 1 1 d . . . C49 C 0.7356(4) 0.2340(3) 0.1315(4) 0.126(2) Uani 1 1 d . . . H49A H 0.7476 0.2212 0.1980 0.190 Uiso 1 1 calc R . . H49B H 0.7341 0.2044 0.0880 0.190 Uiso 1 1 calc R . . H49C H 0.6869 0.2514 0.1128 0.190 Uiso 1 1 calc R . . C50 C -0.2046(4) -0.1559(3) 0.8642(5) 0.149(3) Uani 1 1 d . . . H50A H -0.1986 -0.1670 0.9306 0.223 Uiso 1 1 calc R . . H50B H -0.1994 -0.1864 0.8259 0.223 Uiso 1 1 calc R . . H50C H -0.2540 -0.1403 0.8359 0.223 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 0.0408(16) 0.0564(18) 0.0562(15) -0.0015(12) 0.0171(12) -0.0082(13) C1 0.0427(19) 0.069(3) 0.0446(17) -0.0031(14) 0.0158(13) -0.0041(16) C2 0.0471(19) 0.065(2) 0.0419(16) -0.0021(14) 0.0145(13) -0.0160(17) C3 0.053(2) 0.066(2) 0.0526(18) -0.0030(16) 0.0159(15) -0.0060(18) N2 0.0570(18) 0.063(2) 0.0464(14) 0.0018(12) 0.0154(12) -0.0113(15) C4 0.066(3) 0.080(3) 0.0428(17) 0.0006(16) 0.0127(15) -0.031(2) N3 0.0495(18) 0.088(3) 0.0558(16) -0.0062(15) 0.0190(13) -0.0168(16) C5 0.0436(19) 0.064(2) 0.0604(19) 0.0033(16) 0.0196(15) 0.0000(17) C6 0.051(2) 0.066(2) 0.081(2) -0.0014(18) 0.0219(18) -0.0110(18) C7 0.0457(19) 0.065(2) 0.0491(17) -0.0024(15) 0.0155(14) -0.0045(16) C8 0.055(2) 0.061(2) 0.0502(17) 0.0011(15) 0.0170(15) -0.0038(17) C9 0.057(2) 0.059(2) 0.0574(19) -0.0036(15) 0.0170(16) -0.0045(17) C10 0.072(3) 0.083(3) 0.0471(18) -0.0022(17) 0.0165(17) -0.031(2) C11 0.071(3) 0.110(4) 0.062(2) -0.005(2) 0.0197(19) -0.039(3) C12 0.082(3) 0.073(3) 0.087(3) 0.009(2) 0.028(2) 0.005(2) C13 0.076(3) 0.063(3) 0.089(3) -0.007(2) 0.024(2) -0.008(2) C14 0.084(3) 0.063(3) 0.107(3) -0.005(2) 0.028(3) -0.024(3) C15 0.130(5) 0.092(4) 0.059(2) -0.006(2) 0.021(3) -0.071(4) C16 0.114(4) 0.075(3) 0.065(2) 0.007(2) 0.013(3) -0.036(3) C17 0.058(2) 0.081(3) 0.076(2) -0.006(2) 0.0254(19) 0.007(2) C18 0.114(4) 0.059(3) 0.063(2) 0.0050(18) 0.010(2) -0.023(3) C19 0.065(3) 0.079(3) 0.103(3) -0.006(2) 0.028(2) -0.024(2) N4 0.0422(16) 0.068(2) 0.0489(14) -0.0042(12) 0.0158(11) -0.0052(14) C20 0.0412(18) 0.078(3) 0.0404(16) 0.0020(14) 0.0133(13) 0.0035(17) N6 0.0463(18) 0.107(3) 0.0539(16) 0.0016(15) 0.0164(13) -0.0063(16) C21 0.0434(19) 0.074(3) 0.0426(16) 0.0001(15) 0.0136(13) -0.0061(18) C22 0.057(2) 0.085(3) 0.0493(18) -0.0015(17) 0.0133(16) -0.022(2) N5 0.0506(17) 0.069(2) 0.0482(15) -0.0003(13) 0.0125(12) -0.0080(15) C23 0.058(2) 0.066(2) 0.0404(16) -0.0014(14) 0.0147(14) -0.0110(18) C24 0.060(2) 0.065(2) 0.0429(17) 0.0033(15) 0.0153(15) 0.0019(19) C25 0.063(2) 0.073(3) 0.0543(19) -0.0009(17) 0.0178(16) -0.022(2) C26 0.064(3) 0.107(4) 0.066(2) -0.008(2) 0.0225(19) -0.023(2) C27 0.054(2) 0.081(3) 0.061(2) -0.0017(18) 0.0187(16) -0.013(2) C28 0.048(2) 0.065(2) 0.0469(16) -0.0036(14) 0.0111(14) -0.0051(17) C29 0.050(2) 0.075(3) 0.0433(17) 0.0022(15) 0.0149(14) -0.0026(18) C30 0.068(3) 0.077(3) 0.076(2) -0.0023(19) 0.025(2) 0.003(2) C31 0.066(3) 0.074(3) 0.079(3) -0.001(2) 0.025(2) -0.012(2) C32 0.0401(18) 0.076(3) 0.0508(18) -0.0004(16) 0.0147(14) -0.0002(18) C33 0.106(4) 0.090(4) 0.066(2) -0.008(2) 0.025(2) -0.045(3) C34 0.059(2) 0.091(3) 0.076(2) 0.006(2) 0.0254(19) 0.015(2) C35 0.112(4) 0.077(3) 0.073(3) 0.005(2) 0.025(2) -0.024(3) C36 0.095(3) 0.073(3) 0.072(2) -0.005(2) 0.020(2) -0.016(3) C37 0.069(3) 0.077(3) 0.068(2) 0.0065(19) 0.0227(19) 0.001(2) C38 0.100(4) 0.082(3) 0.075(3) -0.005(2) 0.027(2) -0.025(3) O2 0.0647(18) 0.115(3) 0.090(2) 0.0080(16) 0.0247(15) 0.0040(15) C49 0.145(5) 0.116(4) 0.124(4) -0.009(4) 0.051(4) -0.040(4) C50 0.147(6) 0.137(6) 0.142(5) 0.008(4) 0.015(4) -0.046(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.373(5) . ? N1 C5 1.375(5) . ? N1 C1 1.404(4) . ? C1 C7 1.366(5) . ? C1 C2 1.425(5) . ? C2 N3 1.320(4) . ? C2 N2 1.406(5) . ? C3 C6 1.393(5) . ? C3 C9 1.405(5) . ? N2 C8 1.392(5) . ? N2 C4 1.406(5) . ? C4 C10 1.391(6) . ? C4 C18 1.393(7) . ? N3 C10 1.403(5) . ? C5 C8 1.335(5) . ? C5 H5 0.9300 . ? C6 C19 1.370(6) . ? C6 H6 0.9300 . ? C7 C9 1.414(5) . ? C7 C17 1.498(5) . ? C8 C12 1.486(6) . ? C9 C13 1.401(6) . ? C10 C11 1.401(5) . ? C11 C15 1.377(8) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.386(6) . ? C13 H13 0.9300 . ? C14 C19 1.370(6) . ? C14 H14 0.9300 . ? C15 C16 1.350(8) . ? C15 C50 1.505(7) . ? C16 C18 1.372(6) . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? N4 C32 1.367(5) . ? N4 C23 1.372(5) . ? N4 C20 1.396(4) . ? C20 C29 1.377(5) . ? C20 C21 1.418(5) . ? N6 C21 1.337(4) . ? N6 C25 1.389(6) . ? C21 N5 1.392(5) . ? C22 C25 1.382(6) . ? C22 C36 1.387(6) . ? C22 N5 1.410(5) . ? N5 C28 1.407(4) . ? C23 C27 1.385(5) . ? C23 C24 1.404(5) . ? C24 C37 1.407(6) . ? C24 C29 1.407(5) . ? C25 C26 1.394(5) . ? C26 C33 1.386(7) . ? C26 H26 0.9300 . ? C27 C31 1.366(6) . ? C27 H27 0.9300 . ? C28 C32 1.348(5) . ? C28 C30 1.470(6) . ? C29 C34 1.496(5) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C35 1.408(7) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C38 1.339(7) . ? C33 C49 1.536(7) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C37 1.379(6) . ? C35 H35 0.9300 . ? C36 C38 1.374(6) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 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 C3 N1 C5 128.8(3) . . ? C3 N1 C1 108.2(3) . . ? C5 N1 C1 122.9(3) . . ? C7 C1 N1 109.7(3) . . ? C7 C1 C2 134.2(3) . . ? N1 C1 C2 116.0(3) . . ? N3 C2 N2 112.7(3) . . ? N3 C2 C1 128.7(4) . . ? N2 C2 C1 118.6(3) . . ? N1 C3 C6 129.8(4) . . ? N1 C3 C9 106.9(3) . . ? C6 C3 C9 123.2(4) . . ? C8 N2 C4 131.6(4) . . ? C8 N2 C2 122.4(3) . . ? C4 N2 C2 106.0(3) . . ? C10 C4 C18 121.4(4) . . ? C10 C4 N2 105.2(4) . . ? C18 C4 N2 133.4(4) . . ? C2 N3 C10 104.8(3) . . ? C8 C5 N1 121.5(3) . . ? C8 C5 H5 119.2 . . ? N1 C5 H5 119.2 . . ? C19 C6 C3 116.8(4) . . ? C19 C6 H6 121.6 . . ? C3 C6 H6 121.6 . . ? C1 C7 C9 106.1(3) . . ? C1 C7 C17 127.5(3) . . ? C9 C7 C17 126.4(4) . . ? C5 C8 N2 118.3(3) . . ? C5 C8 C12 122.7(4) . . ? N2 C8 C12 119.0(3) . . ? C13 C9 C3 117.8(4) . . ? C13 C9 C7 133.2(4) . . ? C3 C9 C7 109.0(3) . . ? C4 C10 C11 119.4(4) . . ? C4 C10 N3 111.3(3) . . ? C11 C10 N3 129.3(4) . . ? C15 C11 C10 118.4(5) . . ? C15 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C9 118.5(4) . . ? C14 C13 H13 120.7 . . ? C9 C13 H13 120.8 . . ? C19 C14 C13 122.0(4) . . ? C19 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C16 C15 C11 120.7(4) . . ? C16 C15 C50 114.1(6) . . ? C11 C15 C50 125.2(6) . . ? C15 C16 C18 123.3(5) . . ? C15 C16 H16 118.4 . . ? C18 C16 H16 118.4 . . ? C7 C17 H17A 109.5 . . ? C7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 C4 116.7(5) . . ? C16 C18 H18 121.7 . . ? C4 C18 H18 121.6 . . ? C6 C19 C14 121.6(4) . . ? C6 C19 H19 119.2 . . ? C14 C19 H19 119.2 . . ? C32 N4 C23 128.6(3) . . ? C32 N4 C20 122.8(3) . . ? C23 N4 C20 108.6(3) . . ? C29 C20 N4 109.5(3) . . ? C29 C20 C21 133.9(3) . . ? N4 C20 C21 116.6(3) . . ? C21 N6 C25 105.5(3) . . ? N6 C21 N5 111.7(3) . . ? N6 C21 C20 129.6(4) . . ? N5 C21 C20 118.7(3) . . ? C25 C22 C36 120.7(4) . . ? C25 C22 N5 105.5(4) . . ? C36 C22 N5 133.8(4) . . ? C21 N5 C28 123.0(3) . . ? C21 N5 C22 106.3(3) . . ? C28 N5 C22 130.6(4) . . ? N4 C23 C27 129.8(4) . . ? N4 C23 C24 106.6(3) . . ? C27 C23 C24 123.6(4) . . ? C37 C24 C23 117.4(3) . . ? C37 C24 C29 133.1(4) . . ? C23 C24 C29 109.5(3) . . ? C22 C25 N6 111.1(3) . . ? C22 C25 C26 120.3(4) . . ? N6 C25 C26 128.6(4) . . ? C33 C26 C25 117.8(5) . . ? C33 C26 H26 121.1 . . ? C25 C26 H26 121.1 . . ? C31 C27 C23 118.1(4) . . ? C31 C27 H27 121.0 . . ? C23 C27 H27 121.0 . . ? C32 C28 N5 116.8(3) . . ? C32 C28 C30 123.1(3) . . ? N5 C28 C30 120.1(3) . . ? C20 C29 C24 105.7(3) . . ? C20 C29 C34 126.9(4) . . ? C24 C29 C34 127.3(4) . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 C35 120.1(4) . . ? C27 C31 H31 120.0 . . ? C35 C31 H31 120.0 . . ? C28 C32 N4 122.1(3) . . ? C28 C32 H32 118.9 . . ? N4 C32 H32 118.9 . . ? C38 C33 C26 120.9(5) . . ? C38 C33 C49 115.6(5) . . ? C26 C33 C49 123.4(6) . . ? C29 C34 H34A 109.5 . . ? C29 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C29 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C37 C35 C31 121.8(4) . . ? C37 C35 H35 119.1 . . ? C31 C35 H35 119.1 . . ? C38 C36 C22 117.4(5) . . ? C38 C36 H36 121.3 . . ? C22 C36 H36 121.3 . . ? C35 C37 C24 119.0(4) . . ? C35 C37 H37 120.5 . . ? C24 C37 H37 120.5 . . ? C33 C38 C36 122.8(5) . . ? C33 C38 H38 118.6 . . ? C36 C38 H38 118.6 . . ? C33 C49 H49A 109.5 . . ? C33 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C33 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C15 C50 H50A 109.5 . . ? C15 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C15 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.417 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.103 _database_code_depnum_ccdc_archive 'CCDC 921989'