# Electronic Supplementary Material (ESI) for Chemical Communications # 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_global #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_4,4'-bpe.2HNO3 #TrackingRef 'cif_all.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H12 N4 O6' _chemical_formula_sum 'C12 H12 N4 O6' _chemical_formula_weight 308.26 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 17.4090(7) _cell_length_b 3.66460(10) _cell_length_c 19.9596(9) _cell_angle_alpha 90 _cell_angle_beta 93.836(2) _cell_angle_gamma 90 _cell_volume 1270.51(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100.00(10) _cell_measurement_reflns_used 3070 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 26.51 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.6871 _exptl_absorpt_correction_T_max 0.7454 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100.00(10) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_unetI/netI 0.018 _diffrn_reflns_number 4806 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 1301 _reflns_number_gt 1201 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0362P)^2^+1.3652P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0027(9) _refine_ls_number_reflns 1301 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.252 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.006 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.59476(5) 0.0657(3) 0.18925(4) 0.0220(2) Uani 1 1 d . . . O2 O 0.70522(5) -0.2093(3) 0.20222(4) 0.0180(2) Uani 1 1 d . . . O3 O 0.65341(5) -0.1095(3) 0.10228(4) 0.0236(3) Uani 1 1 d . . . N1 N 0.65057(6) -0.0827(3) 0.16433(5) 0.0154(2) Uani 1 1 d . . . N4 N 0.83978(6) 0.2768(3) 0.16839(5) 0.0161(3) Uani 1 1 d . . . C1 C 0.92335(7) 0.1455(3) 0.05934(6) 0.0145(3) Uani 1 1 d . . . C2 C 0.95243(7) 0.0505(3) 0.12416(6) 0.0155(3) Uani 1 1 d . . . H2 H 1.0006 -0.058 0.1308 0.019 Uiso 1 1 calc R . . C3 C 0.90916(7) 0.1188(3) 0.17758(6) 0.0171(3) Uani 1 1 d . . . H3 H 0.9281 0.0551 0.2207 0.02 Uiso 1 1 calc R . . C5 C 0.80952(7) 0.3706(3) 0.10737(6) 0.0163(3) Uani 1 1 d . . . H5 H 0.7611 0.4786 0.1024 0.02 Uiso 1 1 calc R . . C6 C 0.85056(7) 0.3061(3) 0.05208(6) 0.0157(3) Uani 1 1 d . . . H6 H 0.8297 0.3699 0.0096 0.019 Uiso 1 1 calc R . . C7 C 0.96556(7) 0.0797(3) -0.00048(6) 0.0149(3) Uani 1 1 d . . . H4 H 0.8144(10) 0.317(5) 0.2064(9) 0.036(5) Uiso 1 1 d . . . H7 H 0.9394(9) 0.161(4) -0.0411(8) 0.023(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0177(4) 0.0258(5) 0.0230(5) 0.0001(4) 0.0041(4) 0.0064(4) O2 0.0141(4) 0.0262(5) 0.0135(4) 0.0016(3) -0.0005(3) 0.0038(4) O3 0.0277(5) 0.0324(6) 0.0105(4) 0.0019(4) 0.0003(3) 0.0026(4) N1 0.0156(5) 0.0158(5) 0.0150(5) 0.0011(4) 0.0012(4) -0.0014(4) N4 0.0172(5) 0.0170(5) 0.0146(5) -0.0018(4) 0.0053(4) -0.0020(4) C1 0.0160(6) 0.0118(6) 0.0159(6) -0.0012(5) 0.0025(4) -0.0030(5) C2 0.0152(6) 0.0153(6) 0.0161(6) -0.0003(5) 0.0012(4) 0.0010(5) C3 0.0204(6) 0.0173(6) 0.0133(6) 0.0010(5) 0.0002(5) -0.0013(5) C5 0.0141(6) 0.0162(6) 0.0188(6) -0.0011(5) 0.0012(4) -0.0006(5) C6 0.0168(6) 0.0158(6) 0.0146(6) 0.0005(5) 0.0011(4) -0.0014(5) C7 0.0171(6) 0.0149(6) 0.0128(5) -0.0002(5) 0.0011(4) -0.0013(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 1.2457(13) . ? O2 N1 1.2634(13) . ? O3 N1 1.2466(13) . ? N4 C5 1.3391(16) . ? N4 C3 1.3409(16) . ? N4 H4 0.915(18) . ? C1 C6 1.3959(17) . ? C1 C2 1.4013(16) . ? C1 C7 1.4631(16) . ? C2 C3 1.3692(17) . ? C2 H2 0.93 . ? C3 H3 0.93 . ? C5 C6 1.3748(17) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C7 1.333(2) 5_755 ? C7 H7 0.951(16) . ? 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 O1 N1 O3 120.99(10) . . ? O1 N1 O2 119.83(10) . . ? O3 N1 O2 119.18(10) . . ? C5 N4 C3 122.09(10) . . ? C5 N4 H4 122.0(11) . . ? C3 N4 H4 115.9(11) . . ? C6 C1 C2 118.03(11) . . ? C6 C1 C7 119.13(11) . . ? C2 C1 C7 122.84(11) . . ? C3 C2 C1 119.34(11) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? N4 C3 C2 120.65(11) . . ? N4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? N4 C5 C6 119.47(11) . . ? N4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 120.41(11) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C7 C7 C1 124.12(14) 5_755 . ? C7 C7 H7 121.9(9) 5_755 . ? C1 C7 H7 114.0(9) . . ? _database_code_depnum_ccdc_archive 'CCDC 902210' ####################################################################### # # 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_global #======= END of CIF data_4,4'-tpcb_2 #TrackingRef 'cif_all.cif'.4HNO3 #TrackingRef 'cif_all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N8 O12' _chemical_formula_sum 'C24 H24 N8 O13' _chemical_formula_weight 616.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3344(8) _cell_length_b 10.0039(11) _cell_length_c 10.3610(12) _cell_angle_alpha 85.485(5) _cell_angle_beta 72.352(5) _cell_angle_gamma 70.281(5) _cell_volume 681.72(14) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9733 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _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 5488 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2402 _reflns_number_gt 1953 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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 2316 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.2198 _refine_ls_wR_factor_gt 0.2083 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N3 N 0.9874(3) 0.65466(19) 0.31983(18) 0.0244(5) Uani 1 1 d . . . O1 O 1.1137(2) 0.71781(17) 0.26885(17) 0.0314(5) Uani 1 1 d . . . O2 O 0.8517(3) 0.70173(19) 0.42834(18) 0.0413(5) Uani 1 1 d . . . O3 O 1.0012(3) 0.54597(18) 0.26248(18) 0.0384(5) Uani 1 1 d . . . C1 C 0.2346(4) 0.9703(2) 0.5439(2) 0.0302(6) Uani 1 1 d . . . H1 H 0.2899 1.0424 0.5044 0.036 Uiso 1 1 calc R . . C2 C 0.3311(3) 0.8321(2) 0.4933(2) 0.0274(6) Uani 1 1 d . . . H2 H 0.4529 0.8090 0.4202 0.033 Uiso 1 1 calc R . . C3 C 0.2478(3) 0.7273(2) 0.5505(2) 0.0223(5) Uani 1 1 d . . . C4 C 0.0682(3) 0.7672(2) 0.6570(2) 0.0283(6) Uani 1 1 d . . . H4 H 0.0062 0.6984 0.6965 0.034 Uiso 1 1 calc R . . C5 C -0.0197(3) 0.9053(3) 0.7051(2) 0.0314(6) Uani 1 1 d . . . H5 H -0.1404 0.9316 0.7789 0.038 Uiso 1 1 calc R . . C6 C 0.3453(3) 0.5727(2) 0.5090(2) 0.0207(5) Uani 1 1 d . . . H6 H 0.2436 0.5346 0.4938 0.025 Uiso 1 1 calc R . . C7 C 0.4554(3) 0.4750(2) 0.6095(2) 0.0215(5) Uani 1 1 d . . . H7 H 0.4021 0.3941 0.6379 0.026 Uiso 1 1 calc R . . C8 C 0.4498(3) 0.5498(2) 0.7313(2) 0.0231(5) Uani 1 1 d . . . C9 C 0.5636(3) 0.6384(3) 0.7232(2) 0.0295(6) Uani 1 1 d . . . H9 H 0.6569 0.6479 0.6394 0.035 Uiso 1 1 calc R . . C10 C 0.5407(4) 0.7122(3) 0.8370(3) 0.0354(6) Uani 1 1 d . . . H10 H 0.6185 0.7726 0.8316 0.042 Uiso 1 1 calc R . . C11 C 0.2973(4) 0.6153(3) 0.9667(2) 0.0412(7) Uani 1 1 d . . . H11 H 0.2045 0.6086 1.0518 0.049 Uiso 1 1 calc R . . C12 C 0.3157(4) 0.5386(3) 0.8559(2) 0.0324(6) Uani 1 1 d . . . H12 H 0.2368 0.4782 0.8648 0.039 Uiso 1 1 calc R . . N1 N 0.0658(3) 1.0031(2) 0.6471(2) 0.0294(5) Uani 1 1 d . . . H1' H 0.0084 1.0915 0.6785 0.035 Uiso 1 1 calc R . . N2 N 0.4097(3) 0.6990(2) 0.9547(2) 0.0367(6) Uani 1 1 d . . . H2' H 0.3968 0.7468 1.0265 0.044 Uiso 1 1 calc R . . N4 N 0.6003(4) 0.8727(2) 0.1301(2) 0.0422(6) Uani 1 1 d . . . O4 O 0.4409(3) 0.8449(2) 0.1578(2) 0.0542(6) Uani 1 1 d . . . O5 O 0.7334(5) 0.8265(4) 0.0235(3) 0.1021(12) Uani 1 1 d . . . O6 O 0.6225(5) 0.9450(3) 0.2128(2) 0.0870(10) 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 N3 0.0272(10) 0.0216(10) 0.0233(10) -0.0020(8) -0.0041(8) -0.0089(8) O1 0.0315(9) 0.0279(9) 0.0335(9) -0.0071(7) 0.0018(7) -0.0166(7) O2 0.0415(10) 0.0397(11) 0.0331(10) -0.0095(8) 0.0107(8) -0.0183(8) O3 0.0430(10) 0.0262(10) 0.0454(11) -0.0106(8) -0.0028(8) -0.0175(8) C1 0.0351(13) 0.0230(13) 0.0347(13) -0.0009(10) -0.0117(10) -0.0108(10) C2 0.0268(11) 0.0241(12) 0.0273(12) -0.0008(9) -0.0047(9) -0.0059(9) C3 0.0252(11) 0.0195(12) 0.0228(11) -0.0020(8) -0.0122(9) -0.0033(9) C4 0.0266(12) 0.0254(13) 0.0323(13) -0.0026(10) -0.0054(10) -0.0100(10) C5 0.0265(12) 0.0272(13) 0.0330(13) -0.0080(10) -0.0026(10) -0.0029(10) C6 0.0234(11) 0.0192(12) 0.0189(11) -0.0024(8) -0.0049(9) -0.0067(9) C7 0.0248(11) 0.0194(11) 0.0195(11) 0.0000(8) -0.0048(9) -0.0077(9) C8 0.0254(11) 0.0179(11) 0.0210(11) -0.0011(8) -0.0082(9) 0.0005(9) C9 0.0313(12) 0.0316(14) 0.0239(11) -0.0039(10) -0.0061(9) -0.0090(10) C10 0.0389(14) 0.0341(14) 0.0355(14) -0.0091(11) -0.0150(11) -0.0092(11) C11 0.0426(15) 0.0519(17) 0.0212(12) -0.0063(11) -0.0030(11) -0.0100(13) C12 0.0333(13) 0.0354(14) 0.0258(12) -0.0038(10) -0.0046(10) -0.0107(11) N1 0.0337(11) 0.0190(10) 0.0341(11) -0.0086(8) -0.0116(9) -0.0034(8) N2 0.0419(12) 0.0378(13) 0.0255(11) -0.0139(9) -0.0114(9) -0.0024(10) N4 0.0583(15) 0.0509(15) 0.0311(12) 0.0004(10) -0.0124(11) -0.0355(12) O4 0.0432(11) 0.0769(15) 0.0446(12) -0.0282(11) -0.0008(9) -0.0266(11) O5 0.0811(18) 0.193(4) 0.0538(16) -0.0309(19) 0.0102(14) -0.092(2) O6 0.136(2) 0.116(2) 0.0563(16) -0.0043(15) -0.0325(16) -0.096(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 N3 O3 1.240(2) . ? N3 O2 1.251(2) . ? N3 O1 1.258(2) . ? C1 N1 1.328(3) . ? C1 C2 1.384(3) . ? C1 H1 0.9500 . ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C3 C4 1.395(3) . ? C3 C6 1.503(3) . ? C4 C5 1.373(3) . ? C4 H4 0.9500 . ? C5 N1 1.343(3) . ? C5 H5 0.9500 . ? C6 C7 1.551(3) 2_666 ? C6 C7 1.584(3) . ? C6 H6 1.0000 . ? C7 C8 1.501(3) . ? C7 C6 1.551(3) 2_666 ? C7 H7 1.0000 . ? C8 C12 1.389(3) . ? C8 C9 1.390(3) . ? C9 C10 1.377(3) . ? C9 H9 0.9500 . ? C10 N2 1.333(3) . ? C10 H10 0.9500 . ? C11 N2 1.335(4) . ? C11 C12 1.378(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? N1 H1' 0.8800 . ? N2 H2' 0.8800 . ? N4 O5 1.228(4) . ? N4 O6 1.243(3) . ? N4 O4 1.237(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 O3 N3 O2 121.24(18) . . ? O3 N3 O1 119.38(17) . . ? O2 N3 O1 119.38(18) . . ? N1 C1 C2 120.7(2) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 119.3(2) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 117.9(2) . . ? C2 C3 C6 123.88(19) . . ? C4 C3 C6 118.11(19) . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C5 C4 119.7(2) . . ? N1 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C3 C6 C7 119.34(17) . 2_666 ? C3 C6 C7 115.15(16) . . ? C7 C6 C7 90.64(15) 2_666 . ? C3 C6 H6 110.1 . . ? C7 C6 H6 110.1 2_666 . ? C7 C6 H6 110.1 . . ? C8 C7 C6 119.19(17) . 2_666 ? C8 C7 C6 115.59(17) . . ? C6 C7 C6 89.36(15) 2_666 . ? C8 C7 H7 110.4 . . ? C6 C7 H7 110.4 2_666 . ? C6 C7 H7 110.4 . . ? C12 C8 C9 118.2(2) . . ? C12 C8 C7 119.0(2) . . ? C9 C8 C7 122.67(19) . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? N2 C10 C9 120.1(2) . . ? N2 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N2 C11 C12 120.1(2) . . ? N2 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C8 119.8(2) . . ? C11 C12 H12 120.1 . . ? C8 C12 H12 120.1 . . ? C5 N1 C1 121.8(2) . . ? C5 N1 H1' 119.1 . . ? C1 N1 H1' 119.1 . . ? C10 N2 C11 121.9(2) . . ? C10 N2 H2' 119.1 . . ? C11 N2 H2' 119.1 . . ? O5 N4 O6 121.8(3) . . ? O5 N4 O4 119.5(2) . . ? O6 N4 O4 118.7(2) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.487 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 902211' ####################################################################### # # 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_global #======= END of CIF data_4,4'-tpcb #TrackingRef 'cif_all.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H20 N4' _chemical_formula_sum 'C24 H20 N4' _chemical_formula_weight 364.44 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn _symmetry_space_group_name_Hall '-P 2ab 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 9.3620(4) _cell_length_b 13.9320(3) _cell_length_c 14.0190(4) _cell_angle_alpha 90 _cell_angle_beta 90.0000(10) _cell_angle_gamma 90 _cell_volume 1828.52(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100.00(10) _cell_measurement_reflns_used 9991 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.58 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.9827 _exptl_absorpt_correction_T_max 0.9879 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100.00(10) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_unetI/netI 0.0101 _diffrn_reflns_number 27270 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1874 _reflns_number_gt 1700 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0398P)^2^+0.7889P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0059(11) _refine_ls_number_reflns 1874 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.033 _refine_ls_wR_factor_ref 0.0863 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.274 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.11428(10) 0.59254(7) 0.55571(6) 0.0203(2) Uani 1 1 d . . . N2 N 0.03453(10) 0.46864(7) 0.14654(7) 0.0216(2) Uani 1 1 d . . . C1 C 0.02633(12) 0.59466(8) 0.57116(8) 0.0189(2) Uani 1 1 d . . . H1 H 0.0624 0.5601 0.6244 0.023 Uiso 1 1 calc R . . C2 C 0.12373(12) 0.64413(7) 0.51444(7) 0.0173(2) Uani 1 1 d . . . H2 H 0.2228 0.6428 0.5291 0.021 Uiso 1 1 calc R . . C3 C 0.07414(12) 0.69537(7) 0.43617(7) 0.0155(2) Uani 1 1 d . . . C4 C -0.07208(12) 0.69143(8) 0.41804(8) 0.0201(3) Uani 1 1 d . . . H4 H -0.1109 0.7238 0.3643 0.024 Uiso 1 1 calc R . . C5 C -0.16046(12) 0.64029(8) 0.47854(8) 0.0218(3) Uani 1 1 d . . . H5 H -0.2598 0.6389 0.4646 0.026 Uiso 1 1 calc R . . C6 C 0.16828(10) 0.75651(7) 0.37471(7) 0.0150(2) Uani 1 1 d . . . H6 H 0.1468 0.8254 0.3889 0.018 Uiso 1 1 calc R . . C7 C 0.16641(11) 0.74268(7) 0.26321(7) 0.0154(2) Uani 1 1 d . . . H7 H 0.1163 0.7968 0.2305 0.018 Uiso 1 1 calc R . . C8 C 0.11888(11) 0.64677(7) 0.22513(7) 0.0156(2) Uani 1 1 d . . . C9 C 0.17856(12) 0.56048(8) 0.25559(8) 0.0192(2) Uani 1 1 d . . . H9 H 0.2495 0.5602 0.3041 0.023 Uiso 1 1 calc R . . C10 C 0.13394(12) 0.47509(8) 0.21483(8) 0.0202(3) Uani 1 1 d . . . H10 H 0.1767 0.4173 0.2368 0.024 Uiso 1 1 calc R . . C11 C -0.02411(13) 0.55171(8) 0.11865(8) 0.0233(3) Uani 1 1 d . . . H11 H -0.096 0.5496 0.0708 0.028 Uiso 1 1 calc R . . C12 C 0.01359(12) 0.64079(8) 0.15528(8) 0.0196(3) Uani 1 1 d . . . H12 H -0.0322 0.6973 0.1328 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0217(5) 0.0197(5) 0.0197(5) 0.0008(4) 0.0021(4) -0.0013(4) N2 0.0221(5) 0.0218(5) 0.0210(5) -0.0013(4) -0.0001(4) -0.0048(4) C1 0.0234(6) 0.0171(5) 0.0163(5) 0.0009(4) -0.0009(4) 0.0006(4) C2 0.0166(5) 0.0177(5) 0.0175(5) -0.0019(4) -0.0013(4) 0.0003(4) C3 0.0177(5) 0.0137(5) 0.0152(5) -0.0031(4) 0.0020(4) 0.0004(4) C4 0.0183(6) 0.0241(6) 0.0180(5) 0.0035(4) -0.0009(4) 0.0015(4) C5 0.0170(5) 0.0254(6) 0.0231(6) 0.0022(4) 0.0001(4) -0.0011(4) C6 0.0150(5) 0.0148(5) 0.0151(5) -0.0006(4) -0.0006(4) 0.0007(4) C7 0.0163(5) 0.0153(5) 0.0146(5) 0.0014(4) -0.0005(4) 0.0005(4) C8 0.0149(5) 0.0187(5) 0.0132(5) 0.0006(4) 0.0033(4) -0.0021(4) C9 0.0198(5) 0.0201(5) 0.0176(5) 0.0002(4) -0.0028(4) 0.0000(4) C10 0.0214(5) 0.0185(5) 0.0206(5) 0.0008(4) 0.0012(4) -0.0002(4) C11 0.0218(6) 0.0258(6) 0.0222(6) 0.0003(4) -0.0058(5) -0.0037(5) C12 0.0186(5) 0.0205(5) 0.0197(5) 0.0032(4) -0.0021(4) -0.0009(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.3345(15) . ? N1 C5 1.3416(15) . ? N2 C10 1.3383(15) . ? N2 C11 1.3393(15) . ? C1 C2 1.3923(15) . ? C1 H1 0.95 . ? C2 C3 1.3891(15) . ? C2 H2 0.95 . ? C3 C4 1.3934(16) . ? C3 C6 1.4982(14) . ? C4 C5 1.3825(16) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 C6 1.541(2) 2_565 ? C6 C7 1.5749(14) . ? C6 H6 1 . ? C7 C8 1.5062(14) . ? C7 C7 1.578(2) 2_565 ? C7 H7 1 . ? C8 C12 1.3920(15) . ? C8 C9 1.3928(15) . ? C9 C10 1.3842(15) . ? C9 H9 0.95 . ? C10 H10 0.95 . ? C11 C12 1.3886(16) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? 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 C5 115.97(10) . . ? C10 N2 C11 115.84(10) . . ? N1 C1 C2 124.35(10) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C3 C2 C1 119.12(10) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 116.88(10) . . ? C2 C3 C6 123.36(10) . . ? C4 C3 C6 119.70(9) . . ? C5 C4 C3 119.77(10) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 123.87(11) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C3 C6 C6 121.15(9) . 2_565 ? C3 C6 C7 119.65(9) . . ? C6 C6 C7 89.81(5) 2_565 . ? C3 C6 H6 108.2 . . ? C6 C6 H6 108.2 2_565 . ? C7 C6 H6 108.2 . . ? C8 C7 C6 117.62(8) . . ? C8 C7 C7 114.05(10) . 2_565 ? C6 C7 C7 88.46(5) . 2_565 ? C8 C7 H7 111.6 . . ? C6 C7 H7 111.6 . . ? C7 C7 H7 111.6 2_565 . ? C12 C8 C9 116.62(10) . . ? C12 C8 C7 120.77(9) . . ? C9 C8 C7 122.59(10) . . ? C10 C9 C8 119.61(10) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? N2 C10 C9 124.26(10) . . ? N2 C10 H10 117.9 . . ? C9 C10 H10 117.9 . . ? N2 C11 C12 124.06(10) . . ? N2 C11 H11 118 . . ? C12 C11 H11 118 . . ? C11 C12 C8 119.58(10) . . ? C11 C12 H12 120.2 . . ? C8 C12 H12 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 1.55(16) . . . . ? N1 C1 C2 C3 0.08(17) . . . . ? C1 C2 C3 C4 -1.74(15) . . . . ? C1 C2 C3 C6 175.55(10) . . . . ? C2 C3 C4 C5 1.77(16) . . . . ? C6 C3 C4 C5 -175.62(10) . . . . ? C1 N1 C5 C4 -1.51(17) . . . . ? C3 C4 C5 N1 -0.14(18) . . . . ? C2 C3 C6 C6 18.75(15) . . . 2_565 ? C4 C3 C6 C6 -164.03(9) . . . 2_565 ? C2 C3 C6 C7 128.60(10) . . . . ? C4 C3 C6 C7 -54.18(14) . . . . ? C3 C6 C7 C8 -23.98(14) . . . . ? C6 C6 C7 C8 102.41(11) 2_565 . . . ? C3 C6 C7 C7 -140.47(10) . . . 2_565 ? C6 C6 C7 C7 -14.08(11) 2_565 . . 2_565 ? C6 C7 C8 C12 128.72(10) . . . . ? C7 C7 C8 C12 -129.73(9) 2_565 . . . ? C6 C7 C8 C9 -52.65(14) . . . . ? C7 C7 C8 C9 48.90(12) 2_565 . . . ? C12 C8 C9 C10 1.29(16) . . . . ? C7 C8 C9 C10 -177.39(10) . . . . ? C11 N2 C10 C9 -0.82(17) . . . . ? C8 C9 C10 N2 -0.23(18) . . . . ? C10 N2 C11 C12 0.80(17) . . . . ? N2 C11 C12 C8 0.28(18) . . . . ? C9 C8 C12 C11 -1.31(16) . . . . ? C7 C8 C12 C11 177.40(10) . . . . ? #======= END of CIF _database_code_depnum_ccdc_archive 'CCDC 902212'