# Electronic Supplementary Material (ESI) for RSC Advances # 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_wy209 #TrackingRef '2972_web_deposit_cif_file_0_KenCham-FaiLeung_1288162819.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 F2 N3' _chemical_formula_weight 321.32 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' F F 0.0171 0.0103 '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 35.041(6) _cell_length_b 6.2652(11) _cell_length_c 7.1363(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.850(3) _cell_angle_gamma 90.00 _cell_volume 1564.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 101 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6233 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5197 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.24 _reflns_number_total 1407 _reflns_number_gt 1110 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.0725P)^2^+1.0183P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1407 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 F1 F 0.22324(4) 0.5066(3) 0.0638(2) 0.0875(6) Uani 1 1 d . . . N1 N 0.0000 0.0454(3) 0.2500 0.0407(5) Uani 1 2 d S . . C4 C 0.06639(5) 0.0652(3) 0.1960(3) 0.0437(5) Uani 1 1 d . . . H4A H 0.0649 0.2116 0.2157 0.052 Uiso 1 1 calc R . . C1 C 0.03205(5) -0.0655(3) 0.2210(2) 0.0393(4) Uani 1 1 d . . . C2 C 0.03296(5) -0.2877(3) 0.2179(3) 0.0486(5) Uani 1 1 d . . . H2B H 0.0554 -0.3596 0.1945 0.058 Uiso 1 1 calc R . . C3 C 0.0000 -0.3993(4) 0.2500 0.0549(7) Uani 1 2 d S . . H3 H 0.0000 -0.5478 0.2500 0.066 Uiso 1 2 calc SR . . N2 N 0.09776(4) -0.0131(2) 0.1490(2) 0.0428(4) Uani 1 1 d . . . C5 C 0.12926(5) 0.1252(3) 0.1259(2) 0.0405(4) Uani 1 1 d . . . C6 C 0.16551(5) 0.0507(3) 0.1777(3) 0.0484(5) Uani 1 1 d . . . H6A H 0.1685 -0.0868 0.2253 0.058 Uiso 1 1 calc R . . C7 C 0.19723(5) 0.1792(4) 0.1593(3) 0.0580(6) Uani 1 1 d . . . H7A H 0.2215 0.1314 0.1976 0.070 Uiso 1 1 calc R . . C8 C 0.19201(5) 0.3802(4) 0.0826(3) 0.0565(6) Uani 1 1 d . . . C9 C 0.15690(6) 0.4573(3) 0.0257(3) 0.0523(5) Uani 1 1 d . . . H9A H 0.1543 0.5932 -0.0259 0.063 Uiso 1 1 calc R . . C10 C 0.12540(5) 0.3296(3) 0.0465(3) 0.0454(5) Uani 1 1 d . . . H10A H 0.1013 0.3793 0.0075 0.054 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 F1 0.0617(9) 0.1018(13) 0.0991(12) 0.0071(8) 0.0050(7) -0.0364(8) N1 0.0414(11) 0.0323(11) 0.0485(13) 0.000 0.0043(9) 0.000 C4 0.0451(10) 0.0342(9) 0.0518(11) -0.0014(7) 0.0034(8) -0.0005(7) C1 0.0413(9) 0.0341(10) 0.0423(10) -0.0006(7) 0.0009(7) 0.0016(7) C2 0.0455(10) 0.0335(10) 0.0667(13) -0.0025(8) 0.0009(8) 0.0058(7) C3 0.0568(16) 0.0287(14) 0.079(2) 0.000 0.0000(14) 0.000 N2 0.0409(8) 0.0404(9) 0.0473(9) -0.0004(6) 0.0022(6) 0.0019(6) C5 0.0410(9) 0.0420(10) 0.0386(9) -0.0044(7) 0.0042(7) 0.0003(8) C6 0.0436(10) 0.0510(12) 0.0507(11) 0.0009(8) 0.0034(8) 0.0068(8) C7 0.0386(10) 0.0780(16) 0.0573(13) -0.0019(10) 0.0004(8) 0.0045(9) C8 0.0467(11) 0.0702(15) 0.0528(12) -0.0039(10) 0.0060(8) -0.0170(10) C9 0.0596(12) 0.0500(12) 0.0476(11) 0.0025(8) 0.0059(9) -0.0079(9) C10 0.0425(9) 0.0469(11) 0.0467(11) 0.0014(8) 0.0020(8) 0.0020(8) _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 F1 C8 1.363(2) . ? N1 C1 1.3453(19) . ? N1 C1 1.3454(19) 2 ? C4 N2 1.264(2) . ? C4 C1 1.473(2) . ? C1 C2 1.393(3) . ? C2 C3 1.379(2) . ? C3 C2 1.379(2) 2 ? N2 C5 1.419(2) . ? C5 C6 1.386(2) . ? C5 C10 1.404(3) . ? C6 C7 1.384(3) . ? C7 C8 1.381(3) . ? C8 C9 1.365(3) . ? C9 C10 1.377(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 C1 N1 C1 117.8(2) . 2 ? N2 C4 C1 122.87(17) . . ? N1 C1 C2 122.61(17) . . ? N1 C1 C4 115.13(16) . . ? C2 C1 C4 122.26(16) . . ? C3 C2 C1 118.96(18) . . ? C2 C3 C2 119.0(2) . 2 ? C4 N2 C5 119.05(15) . . ? C6 C5 C10 118.91(17) . . ? C6 C5 N2 118.09(16) . . ? C10 C5 N2 122.95(15) . . ? C7 C6 C5 120.54(19) . . ? C8 C7 C6 118.47(18) . . ? F1 C8 C9 118.8(2) . . ? F1 C8 C7 118.51(19) . . ? C9 C8 C7 122.71(18) . . ? C8 C9 C10 118.53(19) . . ? C9 C10 C5 120.78(17) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.216 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 798464' ####################################################################### # # 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_wy207 #TrackingRef '1807_web_deposit_cif_file_0_Wing-YanWong_1279511277.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H48 Cl F6 N2 O4 P' _chemical_formula_weight 897.30 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 12.0530(4) _cell_length_b 12.8073(4) _cell_length_c 16.0081(9) _cell_angle_alpha 95.8310(10) _cell_angle_beta 99.9830(10) _cell_angle_gamma 114.1490(10) _cell_volume 2179.41(16) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 211 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6068 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25221 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.25 _reflns_number_total 7855 _reflns_number_gt 6456 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.0587P)^2^+0.9095P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7855 _refine_ls_number_parameters 562 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.002 _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 0.12023(13) 0.20595(12) 0.30184(10) 0.0370(3) Uani 1 1 d . . . H1'A H 0.1887 0.2037 0.3330 0.044 Uiso 1 1 calc R . . H1'D H 0.1087 0.1729 0.2468 0.044 Uiso 1 1 calc R . . N1 N -0.14440(13) 0.08695(13) -0.05084(9) 0.0374(3) Uani 1 1 d . . . H1A H -0.1709 0.0093 -0.0645 0.045 Uiso 1 1 calc R . . H1D H -0.0813 0.1145 -0.0031 0.045 Uiso 1 1 calc R . . O1' O 0.59165(13) 0.53425(14) 0.41756(10) 0.0609(4) Uani 1 1 d . . . O2' O 0.43521(15) 0.47905(14) 0.11586(10) 0.0637(4) Uani 1 1 d . . . C1 C -0.09705(17) 0.14183(17) -0.12387(12) 0.0432(4) Uani 1 1 d . . . H1B H -0.0282 0.1250 -0.1335 0.052 Uiso 1 1 calc R . . H1C H -0.0656 0.2258 -0.1083 0.052 Uiso 1 1 calc R . . C2 C -0.19858(17) 0.09708(16) -0.20609(11) 0.0391(4) Uani 1 1 d . . . C3 C -0.23738(19) 0.17348(17) -0.24441(13) 0.0459(4) Uani 1 1 d . . . H3A H -0.2026 0.2519 -0.2189 0.055 Uiso 1 1 calc R . . C4 C -0.3283(2) 0.13051(18) -0.32086(14) 0.0495(5) Uani 1 1 d . . . C5 C -0.38259(19) 0.01310(17) -0.35979(13) 0.0450(4) Uani 1 1 d . . . H5A H -0.4442 -0.0147 -0.4110 0.054 Uiso 1 1 calc R . . C6 C -0.34329(18) -0.06089(16) -0.32100(12) 0.0414(4) Uani 1 1 d . . . C7 C -0.25192(18) -0.01931(17) -0.24388(12) 0.0425(4) Uani 1 1 d . . . H7A H -0.2268 -0.0702 -0.2178 0.051 Uiso 1 1 calc R . . C8 C -0.3163(4) 0.3183(3) -0.3341(2) 0.1159(14) Uani 1 1 d . . . H8A H -0.3564 0.3541 -0.3707 0.174 Uiso 1 1 calc R . . H8B H -0.2291 0.3500 -0.3342 0.174 Uiso 1 1 calc R . . H8C H -0.3251 0.3336 -0.2763 0.174 Uiso 1 1 calc R . . C9 C -0.4867(2) -0.2273(2) -0.42926(16) 0.0653(6) Uani 1 1 d . . . H9A H -0.5074 -0.3085 -0.4458 0.098 Uiso 1 1 calc R . . H9B H -0.4627 -0.1881 -0.4757 0.098 Uiso 1 1 calc R . . H9C H -0.5582 -0.2193 -0.4167 0.098 Uiso 1 1 calc R . . C10 C -0.24984(16) 0.11175(16) -0.03189(12) 0.0394(4) Uani 1 1 d . . . H10A H -0.3144 0.0878 -0.0848 0.047 Uiso 1 1 calc R . . H10B H -0.2190 0.1952 -0.0134 0.047 Uiso 1 1 calc R . . C11 C -0.30741(16) 0.05158(16) 0.03627(12) 0.0379(4) Uani 1 1 d . . . C12 C -0.39419(16) -0.06695(16) 0.01304(13) 0.0417(4) Uani 1 1 d . . . C13 C -0.42295(19) -0.13541(18) -0.07088(15) 0.0525(5) Uani 1 1 d . . . H13A H -0.3820 -0.1016 -0.1122 0.063 Uiso 1 1 calc R . . C14 C -0.5087(2) -0.2485(2) -0.09136(19) 0.0686(7) Uani 1 1 d . . . H14A H -0.5259 -0.2912 -0.1464 0.082 Uiso 1 1 calc R . . C15 C -0.5719(2) -0.3020(2) -0.0301(2) 0.0778(8) Uani 1 1 d . . . H15A H -0.6311 -0.3795 -0.0453 0.093 Uiso 1 1 calc R . . C16 C -0.5475(2) -0.2423(2) 0.0503(2) 0.0667(7) Uani 1 1 d . . . H16A H -0.5891 -0.2795 0.0903 0.080 Uiso 1 1 calc R . . C17 C -0.45864(18) -0.12234(17) 0.07519(15) 0.0486(5) Uani 1 1 d . . . C18 C -0.43710(19) -0.0573(2) 0.15590(14) 0.0530(5) Uani 1 1 d . . . H18A H -0.4804 -0.0933 0.1956 0.064 Uiso 1 1 calc R . . C19 C -0.35298(18) 0.05989(19) 0.17957(13) 0.0468(5) Uani 1 1 d . . . C20 C -0.3346(2) 0.1281(2) 0.26171(14) 0.0615(6) Uani 1 1 d . . . H20A H -0.3807 0.0930 0.3003 0.074 Uiso 1 1 calc R . . C21 C -0.2531(2) 0.2408(3) 0.28477(15) 0.0694(7) Uani 1 1 d . . . H21A H -0.2430 0.2829 0.3387 0.083 Uiso 1 1 calc R . . C22 C -0.1830(2) 0.2953(2) 0.22705(15) 0.0633(6) Uani 1 1 d . . . H22A H -0.1258 0.3734 0.2435 0.076 Uiso 1 1 calc R . . C23 C -0.19720(19) 0.23576(19) 0.14742(14) 0.0515(5) Uani 1 1 d . . . H23A H -0.1494 0.2740 0.1106 0.062 Uiso 1 1 calc R . . C24 C -0.28399(16) 0.11583(17) 0.11937(12) 0.0408(4) Uani 1 1 d . . . C1' C 0.14516(18) 0.33136(16) 0.30483(14) 0.0452(4) Uani 1 1 d . . . H1'B H 0.1402 0.3642 0.3606 0.054 Uiso 1 1 calc R . . H1'C H 0.0827 0.3367 0.2606 0.054 Uiso 1 1 calc R . . C2' C 0.27329(17) 0.39849(15) 0.29020(12) 0.0396(4) Uani 1 1 d . . . C3' C 0.37584(18) 0.44150(16) 0.35963(13) 0.0422(4) Uani 1 1 d . . . H3'A H 0.3649 0.4343 0.4152 0.051 Uiso 1 1 calc R . . C4' C 0.49550(17) 0.49568(16) 0.34580(13) 0.0440(4) Uani 1 1 d . . . C5' C 0.51174(18) 0.50785(17) 0.26363(13) 0.0482(5) Uani 1 1 d . . . H5'A H 0.5919 0.5450 0.2547 0.058 Uiso 1 1 calc R . . C6' C 0.40847(19) 0.46458(16) 0.19427(13) 0.0457(4) Uani 1 1 d . . . C7' C 0.28844(18) 0.41030(16) 0.20699(13) 0.0442(4) Uani 1 1 d . . . H7'A H 0.2191 0.3822 0.1605 0.053 Uiso 1 1 calc R . . C8' C 0.7114(2) 0.5535(3) 0.40424(18) 0.0738(7) Uani 1 1 d . . . H8'A H 0.7712 0.5806 0.4590 0.111 Uiso 1 1 calc R . . H8'B H 0.7363 0.6112 0.3687 0.111 Uiso 1 1 calc R . . H8'C H 0.7078 0.4820 0.3761 0.111 Uiso 1 1 calc R . . C9' C 0.3360(2) 0.4169(2) 0.04153(15) 0.0699(7) Uani 1 1 d . . . H9'A H 0.3659 0.4348 -0.0095 0.105 Uiso 1 1 calc R . . H9'B H 0.2693 0.4392 0.0434 0.105 Uiso 1 1 calc R . . H9'C H 0.3056 0.3347 0.0404 0.105 Uiso 1 1 calc R . . C10' C 0.00906(18) 0.13360(16) 0.33511(14) 0.0465(5) Uani 1 1 d . . . H10C H -0.0675 0.1135 0.2921 0.056 Uiso 1 1 calc R . . H10D H 0.0071 0.1783 0.3870 0.056 Uiso 1 1 calc R . . C11' C 0.01690(17) 0.02353(16) 0.35498(13) 0.0428(4) Uani 1 1 d . . . C12' C -0.05554(17) -0.08443(16) 0.29793(13) 0.0434(4) Uani 1 1 d . . . C13' C -0.14691(19) -0.1019(2) 0.22149(15) 0.0547(5) Uani 1 1 d . . . H13B H -0.1611 -0.0390 0.2074 0.066 Uiso 1 1 calc R . . C14' C -0.2136(2) -0.2080(2) 0.16894(16) 0.0633(6) Uani 1 1 d . . . H14B H -0.2735 -0.2169 0.1201 0.076 Uiso 1 1 calc R . . C15' C -0.1931(2) -0.3047(2) 0.18743(17) 0.0671(6) Uani 1 1 d . . . H15B H -0.2384 -0.3766 0.1503 0.080 Uiso 1 1 calc R . . C16' C -0.1083(2) -0.29352(19) 0.25846(16) 0.0598(6) Uani 1 1 d . . . H16B H -0.0952 -0.3580 0.2696 0.072 Uiso 1 1 calc R . . C17' C -0.03834(18) -0.18514(17) 0.31704(14) 0.0477(5) Uani 1 1 d . . . C18' C 0.0473(2) -0.17431(18) 0.39141(14) 0.0521(5) Uani 1 1 d . . . H18B H 0.0579 -0.2397 0.4031 0.063 Uiso 1 1 calc R . . C19' C 0.11748(19) -0.06918(18) 0.44879(13) 0.0491(5) Uani 1 1 d . . . C20' C 0.2055(2) -0.0593(2) 0.52511(16) 0.0632(6) Uani 1 1 d . . . H20B H 0.2150 -0.1251 0.5372 0.076 Uiso 1 1 calc R . . C21' C 0.2749(3) 0.0435(3) 0.57962(17) 0.0733(7) Uani 1 1 d . . . H21B H 0.3322 0.0485 0.6287 0.088 Uiso 1 1 calc R . . C22' C 0.2610(2) 0.1440(2) 0.56252(16) 0.0692(7) Uani 1 1 d . . . H22B H 0.3090 0.2147 0.6007 0.083 Uiso 1 1 calc R . . C23' C 0.1787(2) 0.13875(19) 0.49136(14) 0.0564(5) Uani 1 1 d . . . H23B H 0.1713 0.2062 0.4816 0.068 Uiso 1 1 calc R . . C24' C 0.10283(18) 0.03229(17) 0.43053(13) 0.0456(4) Uani 1 1 d . . . O1 O -0.3733(2) 0.19582(15) -0.36557(13) 0.0843(6) Uani 1 1 d . . . O2 O -0.38542(16) -0.17685(12) -0.35433(9) 0.0592(4) Uani 1 1 d . . . P1' P 0.0000 0.5000 0.5000 0.04978(19) Uani 1 2 d S . . P1 P 0.0000 0.5000 0.0000 0.0684(3) Uani 1 2 d S . . F1' F 0.13996(14) 0.57935(15) 0.49837(11) 0.0864(5) Uani 1 1 d . . . F1 F -0.0565(3) 0.5182(2) 0.07660(19) 0.1669(12) Uani 1 1 d . . . F2' F 0.01332(15) 0.38637(13) 0.46351(10) 0.0826(5) Uani 1 1 d . . . F2 F 0.13382(19) 0.58743(17) 0.0512(2) 0.1520(11) Uani 1 1 d . . . F3' F -0.04721(15) 0.51342(14) 0.40447(9) 0.0802(4) Uani 1 1 d . . . F3 F 0.01848(18) 0.39343(15) 0.03181(15) 0.1093(6) Uani 1 1 d . . . Cl1 Cl 0.06885(5) 0.12389(4) 0.10541(3) 0.05324(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1' 0.0374(8) 0.0353(8) 0.0392(8) 0.0074(6) 0.0111(6) 0.0157(6) N1 0.0313(7) 0.0456(8) 0.0348(8) 0.0047(6) 0.0051(6) 0.0181(6) O1' 0.0444(8) 0.0783(11) 0.0518(9) 0.0080(7) 0.0024(7) 0.0231(7) O2' 0.0641(9) 0.0703(10) 0.0460(8) 0.0163(7) 0.0172(7) 0.0162(8) C1 0.0374(9) 0.0501(11) 0.0426(10) 0.0093(8) 0.0160(8) 0.0169(8) C2 0.0405(9) 0.0475(10) 0.0364(9) 0.0106(8) 0.0183(8) 0.0217(8) C3 0.0546(11) 0.0391(10) 0.0497(11) 0.0117(8) 0.0200(9) 0.0222(9) C4 0.0602(12) 0.0482(11) 0.0527(12) 0.0184(9) 0.0151(10) 0.0333(10) C5 0.0507(11) 0.0487(11) 0.0405(10) 0.0109(8) 0.0093(8) 0.0265(9) C6 0.0514(11) 0.0418(10) 0.0385(10) 0.0096(8) 0.0154(8) 0.0253(8) C7 0.0535(11) 0.0491(11) 0.0391(10) 0.0132(8) 0.0154(8) 0.0334(9) C8 0.170(4) 0.0593(17) 0.119(3) 0.0170(17) -0.012(2) 0.068(2) C9 0.0719(15) 0.0532(13) 0.0585(14) -0.0014(11) 0.0010(12) 0.0238(11) C10 0.0385(9) 0.0461(10) 0.0406(10) 0.0110(8) 0.0137(8) 0.0230(8) C11 0.0332(9) 0.0459(10) 0.0413(10) 0.0132(8) 0.0114(7) 0.0217(8) C12 0.0337(9) 0.0457(10) 0.0523(11) 0.0130(8) 0.0090(8) 0.0233(8) C13 0.0432(11) 0.0521(12) 0.0608(13) 0.0045(10) 0.0080(9) 0.0226(9) C14 0.0602(14) 0.0531(13) 0.0858(18) -0.0032(12) 0.0022(13) 0.0279(11) C15 0.0616(15) 0.0399(12) 0.121(3) 0.0143(14) 0.0105(15) 0.0164(11) C16 0.0558(13) 0.0509(13) 0.101(2) 0.0337(13) 0.0232(13) 0.0239(11) C17 0.0386(10) 0.0490(11) 0.0678(14) 0.0257(10) 0.0162(9) 0.0237(9) C18 0.0471(11) 0.0696(14) 0.0606(13) 0.0358(11) 0.0261(10) 0.0326(10) C19 0.0413(10) 0.0661(13) 0.0453(11) 0.0205(9) 0.0146(8) 0.0313(10) C20 0.0634(14) 0.0958(19) 0.0434(12) 0.0206(12) 0.0223(10) 0.0467(14) C21 0.0678(15) 0.098(2) 0.0450(13) -0.0024(12) 0.0085(11) 0.0444(15) C22 0.0534(13) 0.0677(15) 0.0596(14) -0.0073(11) 0.0036(11) 0.0258(11) C23 0.0429(11) 0.0569(12) 0.0518(12) 0.0071(10) 0.0120(9) 0.0194(9) C24 0.0352(9) 0.0526(11) 0.0416(10) 0.0133(8) 0.0105(8) 0.0243(8) C1' 0.0432(10) 0.0366(10) 0.0604(12) 0.0107(8) 0.0167(9) 0.0199(8) C2' 0.0402(9) 0.0299(9) 0.0513(11) 0.0092(8) 0.0123(8) 0.0169(7) C3' 0.0478(10) 0.0385(10) 0.0445(10) 0.0120(8) 0.0139(8) 0.0209(8) C4' 0.0411(10) 0.0400(10) 0.0470(11) 0.0052(8) 0.0050(8) 0.0167(8) C5' 0.0405(10) 0.0451(11) 0.0549(12) 0.0112(9) 0.0145(9) 0.0130(8) C6' 0.0513(11) 0.0399(10) 0.0450(11) 0.0124(8) 0.0144(9) 0.0167(9) C7' 0.0441(10) 0.0376(10) 0.0462(11) 0.0088(8) 0.0055(8) 0.0152(8) C8' 0.0480(13) 0.0934(19) 0.0748(17) -0.0001(14) 0.0001(12) 0.0353(13) C9' 0.0755(16) 0.0863(18) 0.0452(13) 0.0190(12) 0.0114(11) 0.0323(14) C10' 0.0421(10) 0.0419(10) 0.0605(12) 0.0145(9) 0.0225(9) 0.0181(8) C11' 0.0390(9) 0.0429(10) 0.0536(11) 0.0161(8) 0.0233(8) 0.0183(8) C12' 0.0374(9) 0.0429(10) 0.0559(12) 0.0152(9) 0.0239(9) 0.0169(8) C13' 0.0460(11) 0.0580(13) 0.0659(14) 0.0139(11) 0.0170(10) 0.0263(10) C14' 0.0484(12) 0.0655(15) 0.0676(15) 0.0029(12) 0.0075(11) 0.0215(11) C15' 0.0628(14) 0.0508(13) 0.0740(16) 0.0009(11) 0.0180(13) 0.0133(11) C16' 0.0657(14) 0.0437(11) 0.0723(15) 0.0144(10) 0.0276(12) 0.0208(10) C17' 0.0459(11) 0.0440(11) 0.0596(13) 0.0174(9) 0.0277(10) 0.0182(9) C18' 0.0574(12) 0.0493(12) 0.0650(13) 0.0259(10) 0.0292(11) 0.0289(10) C19' 0.0499(11) 0.0545(12) 0.0531(12) 0.0226(10) 0.0256(9) 0.0245(9) C20' 0.0682(15) 0.0764(16) 0.0602(14) 0.0296(12) 0.0238(12) 0.0392(13) C21' 0.0707(16) 0.092(2) 0.0560(14) 0.0209(14) 0.0092(12) 0.0345(15) C22' 0.0709(16) 0.0713(16) 0.0524(14) 0.0071(12) 0.0142(12) 0.0197(13) C23' 0.0638(13) 0.0520(12) 0.0528(13) 0.0127(10) 0.0214(11) 0.0211(10) C24' 0.0451(10) 0.0478(11) 0.0487(11) 0.0171(9) 0.0243(9) 0.0178(9) O1 0.1140(15) 0.0560(10) 0.0854(13) 0.0165(9) -0.0108(11) 0.0521(10) O2 0.0832(11) 0.0443(8) 0.0484(8) 0.0031(6) 0.0003(7) 0.0334(8) P1' 0.0521(4) 0.0565(4) 0.0450(4) 0.0045(3) 0.0092(3) 0.0298(4) P1 0.0562(5) 0.0375(4) 0.1056(8) 0.0109(4) 0.0303(5) 0.0108(4) F1' 0.0580(8) 0.0972(11) 0.0990(12) 0.0230(9) 0.0217(8) 0.0267(8) F1 0.243(3) 0.150(2) 0.179(3) 0.0573(19) 0.142(2) 0.112(2) F2' 0.0977(11) 0.0764(10) 0.0830(10) -0.0051(8) 0.0128(8) 0.0551(9) F2 0.0821(13) 0.0723(12) 0.247(3) 0.0085(15) -0.0179(16) 0.0077(10) F3' 0.0969(11) 0.0941(11) 0.0513(8) 0.0134(7) 0.0046(7) 0.0485(9) F3 0.0981(13) 0.0654(10) 0.1680(19) 0.0397(11) 0.0341(13) 0.0341(9) Cl1 0.0623(3) 0.0535(3) 0.0412(3) 0.0011(2) -0.0060(2) 0.0315(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1' C1' 1.502(2) . ? N1' C10' 1.506(2) . ? N1 C10 1.501(2) . ? N1 C1 1.502(2) . ? O1' C4' 1.364(2) . ? O1' C8' 1.420(3) . ? O2' C6' 1.361(2) . ? O2' C9' 1.420(3) . ? C1 C2 1.508(3) . ? C2 C7 1.378(3) . ? C2 C3 1.396(3) . ? C3 C4 1.381(3) . ? C4 O1 1.365(2) . ? C4 C5 1.393(3) . ? C5 C6 1.376(3) . ? C6 O2 1.370(2) . ? C6 C7 1.391(3) . ? C8 O1 1.423(3) . ? C9 O2 1.427(3) . ? C10 C11 1.504(2) . ? C11 C24 1.409(3) . ? C11 C12 1.410(3) . ? C12 C13 1.430(3) . ? C12 C17 1.434(3) . ? C13 C14 1.354(3) . ? C14 C15 1.407(4) . ? C15 C16 1.347(4) . ? C16 C17 1.431(3) . ? C17 C18 1.385(3) . ? C18 C19 1.389(3) . ? C19 C20 1.431(3) . ? C19 C24 1.437(3) . ? C20 C21 1.338(4) . ? C21 C22 1.405(4) . ? C22 C23 1.362(3) . ? C23 C24 1.427(3) . ? C1' C2' 1.503(3) . ? C2' C3' 1.382(3) . ? C2' C7' 1.390(3) . ? C3' C4' 1.391(3) . ? C4' C5' 1.378(3) . ? C5' C6' 1.386(3) . ? C6' C7' 1.388(3) . ? C10' C11' 1.512(3) . ? C11' C12' 1.410(3) . ? C11' C24' 1.411(3) . ? C12' C13' 1.427(3) . ? C12' C17' 1.441(3) . ? C13' C14' 1.356(3) . ? C14' C15' 1.408(4) . ? C15' C16' 1.342(4) . ? C16' C17' 1.422(3) . ? C17' C18' 1.387(3) . ? C18' C19' 1.386(3) . ? C19' C20' 1.430(3) . ? C19' C24' 1.433(3) . ? C20' C21' 1.344(4) . ? C21' C22' 1.411(4) . ? C22' C23' 1.350(3) . ? C23' C24' 1.430(3) . ? P1' F1' 1.5801(15) 2_566 ? P1' F1' 1.5802(15) . ? P1' F3' 1.5886(14) 2_566 ? P1' F3' 1.5886(14) . ? P1' F2' 1.5924(13) 2_566 ? P1' F2' 1.5924(13) . ? P1 F1 1.543(2) . ? P1 F1 1.543(2) 2_565 ? P1 F2 1.5505(19) . ? P1 F2 1.5505(19) 2_565 ? P1 F3 1.5882(17) 2_565 ? P1 F3 1.5882(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1' N1' C10' 115.38(14) . . ? C10 N1 C1 111.79(14) . . ? C4' O1' C8' 116.97(17) . . ? C6' O2' C9' 117.20(17) . . ? N1 C1 C2 111.54(14) . . ? C7 C2 C3 120.10(18) . . ? C7 C2 C1 119.74(17) . . ? C3 C2 C1 120.15(17) . . ? C4 C3 C2 118.83(18) . . ? O1 C4 C3 124.79(19) . . ? O1 C4 C5 113.64(19) . . ? C3 C4 C5 121.57(18) . . ? C6 C5 C4 118.76(18) . . ? O2 C6 C5 124.49(18) . . ? O2 C6 C7 114.94(16) . . ? C5 C6 C7 120.54(17) . . ? C2 C7 C6 120.19(17) . . ? N1 C10 C11 114.14(14) . . ? C24 C11 C12 120.76(17) . . ? C24 C11 C10 120.15(16) . . ? C12 C11 C10 118.80(16) . . ? C11 C12 C13 122.94(18) . . ? C11 C12 C17 119.33(18) . . ? C13 C12 C17 117.73(18) . . ? C14 C13 C12 121.3(2) . . ? C13 C14 C15 120.6(2) . . ? C16 C15 C14 120.8(2) . . ? C15 C16 C17 120.9(2) . . ? C18 C17 C16 122.0(2) . . ? C18 C17 C12 119.27(18) . . ? C16 C17 C12 118.7(2) . . ? C17 C18 C19 122.17(18) . . ? C18 C19 C20 122.1(2) . . ? C18 C19 C24 119.39(18) . . ? C20 C19 C24 118.5(2) . . ? C21 C20 C19 122.1(2) . . ? C20 C21 C22 119.6(2) . . ? C23 C22 C21 121.2(2) . . ? C22 C23 C24 121.3(2) . . ? C11 C24 C23 123.80(17) . . ? C11 C24 C19 119.01(18) . . ? C23 C24 C19 117.16(18) . . ? N1' C1' C2' 109.31(14) . . ? C3' C2' C7' 120.73(17) . . ? C3' C2' C1' 119.04(17) . . ? C7' C2' C1' 120.10(17) . . ? C2' C3' C4' 119.51(18) . . ? O1' C4' C5' 123.86(18) . . ? O1' C4' C3' 115.83(17) . . ? C5' C4' C3' 120.31(18) . . ? C4' C5' C6' 119.89(18) . . ? O2' C6' C5' 115.05(17) . . ? O2' C6' C7' 124.44(18) . . ? C5' C6' C7' 120.51(18) . . ? C6' C7' C2' 119.05(18) . . ? N1' C10' C11' 110.11(14) . . ? C12' C11' C24' 120.54(18) . . ? C12' C11' C10' 121.15(18) . . ? C24' C11' C10' 118.25(18) . . ? C11' C12' C13' 124.29(18) . . ? C11' C12' C17' 118.90(18) . . ? C13' C12' C17' 116.81(18) . . ? C14' C13' C12' 121.6(2) . . ? C13' C14' C15' 120.8(2) . . ? C16' C15' C14' 120.3(2) . . ? C15' C16' C17' 121.3(2) . . ? C18' C17' C16' 121.2(2) . . ? C18' C17' C12' 119.55(19) . . ? C16' C17' C12' 119.2(2) . . ? C19' C18' C17' 122.13(19) . . ? C18' C19' C20' 121.5(2) . . ? C18' C19' C24' 119.22(19) . . ? C20' C19' C24' 119.3(2) . . ? C21' C20' C19' 121.1(2) . . ? C20' C21' C22' 120.2(2) . . ? C23' C22' C21' 120.8(2) . . ? C22' C23' C24' 121.8(2) . . ? C11' C24' C23' 123.49(19) . . ? C11' C24' C19' 119.64(18) . . ? C23' C24' C19' 116.9(2) . . ? C4 O1 C8 117.5(2) . . ? C6 O2 C9 117.73(16) . . ? F1' P1' F1' 180.000(1) 2_566 . ? F1' P1' F3' 90.56(9) 2_566 2_566 ? F1' P1' F3' 89.44(9) . 2_566 ? F1' P1' F3' 89.44(9) 2_566 . ? F1' P1' F3' 90.56(9) . . ? F3' P1' F3' 180.00(12) 2_566 . ? F1' P1' F2' 90.62(9) 2_566 2_566 ? F1' P1' F2' 89.38(9) . 2_566 ? F3' P1' F2' 90.66(8) 2_566 2_566 ? F3' P1' F2' 89.34(8) . 2_566 ? F1' P1' F2' 89.38(9) 2_566 . ? F1' P1' F2' 90.62(9) . . ? F3' P1' F2' 89.34(8) 2_566 . ? F3' P1' F2' 90.66(8) . . ? F2' P1' F2' 180.000(1) 2_566 . ? F1 P1 F1 180.0 . 2_565 ? F1 P1 F2 91.91(18) . . ? F1 P1 F2 88.09(18) 2_565 . ? F1 P1 F2 88.09(18) . 2_565 ? F1 P1 F2 91.91(18) 2_565 2_565 ? F2 P1 F2 179.999(1) . 2_565 ? F1 P1 F3 88.23(13) . 2_565 ? F1 P1 F3 91.77(13) 2_565 2_565 ? F2 P1 F3 88.33(11) . 2_565 ? F2 P1 F3 91.67(11) 2_565 2_565 ? F1 P1 F3 91.77(13) . . ? F1 P1 F3 88.23(13) 2_565 . ? F2 P1 F3 91.67(11) . . ? F2 P1 F3 88.33(11) 2_565 . ? F3 P1 F3 180.0 2_565 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.424 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 784761' ####################################################################### # # 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_WY206 #TrackingRef '1808_web_deposit_cif_file_1_Wing-YanWong_1279511277.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 N3 O2' _chemical_formula_weight 345.39 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 7.1660(6) _cell_length_b 40.204(3) _cell_length_c 6.3427(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1827.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 205 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6521 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6680 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -52 _diffrn_reflns_limit_k_max 52 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 27.95 _reflns_number_total 2019 _reflns_number_gt 1226 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.0489P)^2^+0.2607P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 2019 _refine_ls_number_parameters 119 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0094(2) 0.21104(4) 0.4471(3) 0.0532(5) Uani 1 1 d . . . C1 C -0.0030(4) 0.02853(6) 0.0154(4) 0.0480(7) Uani 1 1 d . . . C2 C -0.0043(4) 0.02929(6) -0.2011(5) 0.0600(8) Uani 1 1 d . . . H2A H -0.0081 0.0495 -0.2723 0.072 Uiso 1 1 calc R . . C3 C 0.0000 0.0000 -0.3110(7) 0.0702(13) Uani 1 2 d S . . H3 H 0.0000 0.0000 -0.4577 0.084 Uiso 1 2 calc SR . . C4 C -0.0085(4) 0.05928(6) 0.1405(5) 0.0546(8) Uani 1 1 d . . . H4A H -0.0121 0.0579 0.2868 0.066 Uiso 1 1 calc R . . C5 C -0.0068(3) 0.11730(5) 0.1698(4) 0.0406(6) Uani 1 1 d . . . C6 C -0.0872(3) 0.14493(5) 0.0739(4) 0.0436(6) Uani 1 1 d . . . H6A H -0.1415 0.1427 -0.0585 0.052 Uiso 1 1 calc R . . C7 C -0.0881(3) 0.17543(5) 0.1708(4) 0.0422(6) Uani 1 1 d . . . H7A H -0.1460 0.1934 0.1059 0.051 Uiso 1 1 calc R . . C8 C -0.0028(3) 0.17949(5) 0.3653(4) 0.0408(6) Uani 1 1 d . . . C9 C 0.0821(3) 0.15265(6) 0.4624(4) 0.0469(6) Uani 1 1 d . . . H9A H 0.1418 0.1553 0.5915 0.056 Uiso 1 1 calc R . . C10 C 0.0769(3) 0.12183(6) 0.3649(4) 0.0470(6) Uani 1 1 d . . . H10A H 0.1310 0.1037 0.4322 0.056 Uiso 1 1 calc R . . C11 C 0.0842(5) 0.21732(6) 0.6407(5) 0.0695(8) Uani 1 1 d . . . H11A H 0.0669 0.2402 0.6801 0.104 Uiso 1 1 calc R . . H11B H 0.2150 0.2128 0.6242 0.104 Uiso 1 1 calc R . . H11C H 0.0339 0.2032 0.7486 0.104 Uiso 1 1 calc R . . N1 N 0.0000 0.0000 0.1255(5) 0.0523(9) Uani 1 2 d S . . N2 N -0.0084(3) 0.08737(5) 0.0531(4) 0.0465(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0713(11) 0.0355(8) 0.0527(11) -0.0014(8) -0.0061(12) 0.0037(8) C1 0.067(2) 0.0364(15) 0.0410(17) -0.0001(11) 0.0014(13) -0.0018(11) C2 0.097(2) 0.0396(14) 0.0438(18) 0.0066(13) -0.0042(16) 0.0001(14) C3 0.123(4) 0.055(2) 0.033(2) 0.000 0.000 -0.001(2) C4 0.082(2) 0.0401(14) 0.0416(16) 0.0009(12) 0.0046(16) -0.0040(12) C5 0.0468(13) 0.0337(12) 0.0414(15) 0.0020(11) -0.0013(15) -0.0017(10) C6 0.0504(15) 0.0431(13) 0.0373(14) 0.0035(11) -0.0047(14) 0.0007(11) C7 0.0485(13) 0.0345(12) 0.0437(15) 0.0080(12) -0.0032(15) 0.0033(10) C8 0.0442(11) 0.0325(11) 0.0457(17) 0.0031(10) 0.0057(13) 0.0008(10) C9 0.0558(14) 0.0424(13) 0.0423(14) 0.0030(12) -0.0060(14) 0.0000(11) C10 0.0549(15) 0.0354(12) 0.0507(17) 0.0073(11) -0.0071(15) 0.0033(10) C11 0.098(2) 0.0476(15) 0.063(2) -0.0137(15) -0.0163(19) -0.0001(15) N1 0.080(2) 0.0360(15) 0.0405(19) 0.000 0.000 -0.0053(13) N2 0.0557(14) 0.0367(11) 0.0470(12) -0.0008(9) -0.0031(11) -0.0021(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.371(2) . ? O1 C11 1.422(3) . ? C1 N1 1.343(3) . ? C1 C2 1.374(4) . ? C1 C4 1.469(3) . ? C2 C3 1.369(3) . ? C3 C2 1.369(3) 2 ? C4 N2 1.258(3) . ? C5 C10 1.387(4) . ? C5 C6 1.391(3) . ? C5 N2 1.413(3) . ? C6 C7 1.371(3) . ? C7 C8 1.387(4) . ? C8 C9 1.383(3) . ? C9 C10 1.385(3) . ? N1 C1 1.343(3) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 C11 118.31(18) . . ? N1 C1 C2 122.6(2) . . ? N1 C1 C4 116.0(2) . . ? C2 C1 C4 121.4(2) . . ? C3 C2 C1 119.3(3) . . ? C2 C3 C2 118.8(4) 2 . ? N2 C4 C1 121.2(2) . . ? C10 C5 C6 117.7(2) . . ? C10 C5 N2 125.6(2) . . ? C6 C5 N2 116.6(2) . . ? C7 C6 C5 121.3(2) . . ? C6 C7 C8 120.1(2) . . ? O1 C8 C9 124.7(2) . . ? O1 C8 C7 115.5(2) . . ? C9 C8 C7 119.9(2) . . ? C8 C9 C10 119.2(2) . . ? C9 C10 C5 121.8(2) . . ? C1 N1 C1 117.3(3) 2 . ? C4 N2 C5 122.3(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.123 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 784762' ####################################################################### # # 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_wy201 #TrackingRef '1809_web_deposit_cif_file_2_Wing-YanWong_1279511277.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 N3' _chemical_formula_weight 313.39 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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 4.7249(7) _cell_length_b 6.2811(9) _cell_length_c 28.965(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.639(3) _cell_angle_gamma 90.00 _cell_volume 856.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 112 _cell_measurement_theta_min 15 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5906 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11557 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1566 _reflns_number_gt 1391 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.31(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1566 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1810 _refine_ls_R_factor_gt 0.1742 _refine_ls_wR_factor_ref 0.6184 _refine_ls_wR_factor_gt 0.6124 _refine_ls_goodness_of_fit_ref 3.356 _refine_ls_restrained_S_all 3.356 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.003 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 0.0000 0.6305(10) 0.2500 0.048(2) Uani 1 2 d S . . N2 N 0.5501(10) 0.6935(8) 0.33998(16) 0.0534(19) Uani 1 1 d . . . C1 C 0.0000 1.0724(13) 0.2500 0.060(3) Uani 1 2 d S . . H1 H 0.0000 1.2205 0.2500 0.072 Uiso 1 2 calc SR . . C2 C 0.1842(12) 0.9622(10) 0.2801(2) 0.056(2) Uani 1 1 d . . . H2B H 0.3109 1.0346 0.3008 0.067 Uiso 1 1 calc R . . C3 C 0.1797(11) 0.7400(9) 0.27947(17) 0.0452(18) Uani 1 1 d . . . C4 C 0.3709(12) 0.6109(9) 0.31073(19) 0.0499(19) Uani 1 1 d . . . H4A H 0.3592 0.4633 0.3088 0.060 Uiso 1 1 calc R . . C5 C 0.7361(12) 0.5638(9) 0.3683(2) 0.0484(18) Uani 1 1 d . . . C6 C 0.8606(15) 0.6494(11) 0.4085(2) 0.063(2) Uani 1 1 d . . . H6A H 0.8150 0.7878 0.4166 0.075 Uiso 1 1 calc R . . C7 C 1.0497(14) 0.5365(12) 0.4369(2) 0.068(2) Uani 1 1 d . . . H7A H 1.1286 0.6001 0.4639 0.081 Uiso 1 1 calc R . . C8 C 1.1291(13) 0.3287(12) 0.4268(2) 0.061(2) Uani 1 1 d . . . C9 C 1.0077(14) 0.2446(11) 0.3848(2) 0.064(2) Uani 1 1 d . . . H9A H 1.0580 0.1079 0.3763 0.077 Uiso 1 1 calc R . . C10 C 0.8197(14) 0.3556(10) 0.3563(2) 0.059(2) Uani 1 1 d . . . H10A H 0.7450 0.2947 0.3287 0.071 Uiso 1 1 calc R . . C11 C 1.3379(17) 0.2040(15) 0.4572(3) 0.086(3) Uani 1 1 d . . . H11A H 1.3978 0.2867 0.4841 0.129 Uiso 1 1 calc R . . H11B H 1.4996 0.1703 0.4405 0.129 Uiso 1 1 calc R . . H11C H 1.2506 0.0747 0.4666 0.129 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 0.049(4) 0.039(3) 0.052(4) 0.000 -0.012(3) 0.000 N2 0.061(3) 0.048(3) 0.049(3) -0.003(2) -0.006(2) -0.004(2) C1 0.070(6) 0.038(4) 0.071(6) 0.000 -0.003(4) 0.000 C2 0.064(4) 0.046(4) 0.057(4) -0.005(2) 0.002(3) -0.004(2) C3 0.052(4) 0.041(3) 0.043(3) -0.002(2) 0.003(2) -0.010(2) C4 0.053(4) 0.044(3) 0.051(4) 0.004(2) -0.007(3) -0.009(2) C5 0.047(3) 0.049(3) 0.048(3) 0.004(2) -0.001(2) -0.004(2) C6 0.075(4) 0.056(4) 0.055(4) 0.002(3) -0.004(3) 0.001(3) C7 0.065(4) 0.080(5) 0.054(4) 0.001(3) -0.017(3) -0.004(3) C8 0.049(4) 0.074(4) 0.059(4) 0.014(3) -0.002(3) -0.001(3) C9 0.065(4) 0.059(4) 0.067(4) 0.005(3) -0.001(3) 0.007(3) C10 0.062(4) 0.062(4) 0.051(3) -0.007(3) -0.006(3) -0.001(3) C11 0.086(5) 0.098(6) 0.071(5) 0.023(4) -0.012(4) 0.024(4) _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 1.344(6) . ? N1 C3 1.344(6) 2 ? N2 C4 1.260(6) . ? N2 C5 1.411(7) . ? C1 C2 1.369(7) . ? C1 C2 1.369(7) 2 ? C2 C3 1.396(9) . ? C3 C4 1.470(7) . ? C5 C6 1.372(8) . ? C5 C10 1.417(9) . ? C6 C7 1.363(8) . ? C7 C8 1.396(11) . ? C8 C9 1.404(9) . ? C8 C11 1.491(8) . ? C9 C10 1.356(8) . ? 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 C3 118.4(6) . 2 ? C4 N2 C5 120.4(5) . . ? C2 C1 C2 119.3(7) . 2 ? C1 C2 C3 119.2(5) . . ? N1 C3 C2 121.9(5) . . ? N1 C3 C4 115.7(5) . . ? C2 C3 C4 122.3(5) . . ? N2 C4 C3 122.2(5) . . ? C6 C5 N2 118.1(5) . . ? C6 C5 C10 117.4(5) . . ? N2 C5 C10 124.3(5) . . ? C7 C6 C5 121.5(6) . . ? C6 C7 C8 122.3(6) . . ? C7 C8 C9 115.8(6) . . ? C7 C8 C11 122.9(6) . . ? C9 C8 C11 121.3(7) . . ? C10 C9 C8 122.4(6) . . ? C9 C10 C5 120.5(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.544 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.136 _database_code_depnum_ccdc_archive 'CCDC 784763'