# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Piero Macchi' 'Cristina Bazzini' 'Tullio Caronna' 'Francesca Fontana' 'Andrea Mele' 'Walter Panzeri' 'A Sironi' 'Isabella Natali Sora' _publ_contact_author_name 'Piero Macchi' _publ_contact_author_email PIERO.MACCHI@UNIMI.IT _publ_section_title ; Synthesis, Crystal Structure and Crystal Packing of Diaza[5]Helicenes ; _publ_requested_category FO # Attachment 'B800050F_archive.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-12-29 at 18:14:44 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\programmi\wingx\files\archive.dat # CIF files read : new data_1 _database_code_depnum_ccdc_archive 'CCDC 686815' _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H12 N2' _chemical_formula_weight 280.32 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 15.7823(7) _cell_length_b 8.7508(4) _cell_length_c 19.8826(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2745.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5356 _cell_measurement_theta_max 24.1 _cell_measurement_theta_min 2.4 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_unetI/netI 0.0215 _diffrn_reflns_number 24627 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 23.25 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1965 _reflns_number_gt 1893 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0499P)^2^+3.7710P] 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_number_reflns 1965 _refine_ls_number_parameters 247 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.1736 _refine_ls_wR_factor_gt 0.1721 _refine_ls_goodness_of_fit_ref 1.303 _refine_ls_restrained_S_all 1.298 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.201 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # 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 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' N N 0.0061 0.0033 '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 C1 C 0.1672(2) 0.4281(4) -0.06653(17) 0.0384(9) Uani 1 1 d D . . C2 C 0.1723(3) 0.3247(5) -0.01476(19) 0.0478(10) Uani 1 1 d D . . C3 C 0.1364(3) 0.3621(6) 0.0473(2) 0.0596(12) Uani 1 1 d D . . N4 N 0.1036(2) 0.4972(5) 0.06102(17) 0.0591(10) Uani 1 1 d . . . C5 C 0.0783(3) 0.7543(6) 0.0283(2) 0.0563(12) Uani 1 1 d D . . C6 C 0.0874(3) 0.8675(5) -0.0167(2) 0.0552(12) Uani 1 1 d D . . C7 C 0.1272(3) 0.9639(4) -0.1294(2) 0.0542(12) Uani 1 1 d D . . C8 C 0.1561(3) 0.9380(5) -0.1920(2) 0.0517(11) Uani 1 1 d D . . C9 C 0.1829(2) 0.7630(5) -0.2869(2) 0.0494(11) Uani 1 1 d D . . C10 C 0.1766(2) 0.6250(5) -0.31565(18) 0.0446(10) Uani 1 1 d D . . N11 N 0.1199(2) 0.3745(4) -0.31641(15) 0.0437(8) Uani 1 1 d . . . C12 C 0.0743(2) 0.2679(5) -0.28715(19) 0.0450(10) Uani 1 1 d D . . C13 C 0.0412(2) 0.2824(4) -0.22257(19) 0.0401(9) Uani 1 1 d D . . C14 C 0.0597(2) 0.4089(4) -0.18545(17) 0.0337(8) Uani 1 1 d D . . C15 C 0.1280(2) 0.5702(4) -0.05597(17) 0.0351(9) Uani 1 1 d . . . C16 C 0.1022(2) 0.6020(5) 0.01027(18) 0.0439(10) Uani 1 1 d . . . C17 C 0.1227(2) 0.6886(4) -0.10724(17) 0.0350(9) Uani 1 1 d . . . C18 C 0.1114(2) 0.8402(4) -0.0850(2) 0.0435(10) Uani 1 1 d . . . C19 C 0.1342(2) 0.6628(4) -0.17830(17) 0.0327(8) Uani 1 1 d . . . C20 C 0.1597(2) 0.7879(4) -0.21825(19) 0.0404(9) Uani 1 1 d . . . C21 C 0.1129(2) 0.5225(4) -0.21240(17) 0.0318(8) Uani 1 1 d . . . C22 C 0.1370(2) 0.5035(4) -0.28077(18) 0.0374(9) Uani 1 1 d . . . H1 H 0.196(2) 0.397(4) -0.1141(9) 0.050(11) Uiso 1 1 d D . . H2 H 0.206(2) 0.218(2) -0.022(2) 0.058(12) Uiso 1 1 d D . . H3 H 0.139(3) 0.276(4) 0.0860(19) 0.112(19) Uiso 1 1 d D . . H5 H 0.060(2) 0.769(5) 0.0802(6) 0.064(12) Uiso 1 1 d D . . H6 H 0.075(2) 0.9857(13) -0.0046(19) 0.051(11) Uiso 1 1 d D . . H7 H 0.120(3) 1.078(2) -0.110(2) 0.081(15) Uiso 1 1 d D . . H8 H 0.175(2) 1.028(3) -0.2260(16) 0.063(12) Uiso 1 1 d D . . H9 H 0.206(2) 0.859(3) -0.3156(15) 0.051(11) Uiso 1 1 d D . . H10 H 0.195(3) 0.610(5) -0.3676(7) 0.074(14) Uiso 1 1 d D . . H12 H 0.060(2) 0.166(3) -0.3159(17) 0.061(12) Uiso 1 1 d D . . H13 H -0.0004(17) 0.198(3) -0.2010(15) 0.039(9) Uiso 1 1 d D . . H14 H 0.032(2) 0.422(4) -0.1360(8) 0.048(10) Uiso 1 1 d 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 C1 0.040(2) 0.045(2) 0.0299(19) 0.0003(17) 0.0003(16) -0.0044(18) C2 0.055(2) 0.050(2) 0.039(2) 0.005(2) 0.0000(19) -0.006(2) C3 0.071(3) 0.073(3) 0.035(2) 0.014(2) 0.002(2) -0.007(3) N4 0.070(2) 0.074(3) 0.0326(19) 0.0003(19) 0.0059(17) -0.011(2) C5 0.054(3) 0.073(3) 0.042(2) -0.025(2) 0.004(2) -0.008(2) C6 0.048(2) 0.051(3) 0.067(3) -0.025(2) 0.001(2) 0.006(2) C7 0.054(3) 0.032(2) 0.077(3) -0.004(2) -0.017(2) 0.000(2) C8 0.052(2) 0.039(2) 0.064(3) 0.010(2) -0.018(2) -0.0019(19) C9 0.044(2) 0.054(3) 0.050(2) 0.027(2) -0.0080(19) -0.010(2) C10 0.040(2) 0.059(3) 0.035(2) 0.013(2) 0.0000(17) 0.0005(19) N11 0.0450(18) 0.052(2) 0.0340(17) -0.0059(16) -0.0011(14) 0.0019(16) C12 0.047(2) 0.046(2) 0.041(2) -0.0087(19) -0.0040(19) 0.000(2) C13 0.041(2) 0.040(2) 0.039(2) -0.0019(17) -0.0014(17) -0.0046(17) C14 0.0357(19) 0.035(2) 0.0310(18) 0.0035(16) -0.0046(15) -0.0007(16) C15 0.0310(18) 0.042(2) 0.0323(19) -0.0037(17) -0.0018(15) -0.0047(16) C16 0.040(2) 0.056(3) 0.036(2) -0.0109(19) -0.0007(17) -0.0101(19) C17 0.0343(19) 0.0331(19) 0.037(2) -0.0057(16) -0.0060(16) -0.0015(16) C18 0.039(2) 0.041(2) 0.051(2) -0.0104(19) -0.0069(18) 0.0031(17) C19 0.0285(18) 0.0335(19) 0.0360(19) 0.0053(16) -0.0036(15) 0.0021(15) C20 0.0334(19) 0.040(2) 0.048(2) 0.0095(18) -0.0085(17) -0.0007(16) C21 0.0283(18) 0.0341(19) 0.0330(19) 0.0054(15) -0.0033(15) 0.0029(15) C22 0.034(2) 0.046(2) 0.0321(19) 0.0049(17) -0.0007(16) 0.0051(17) #----------------------------------------------------------------------------# # 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 C1 C2 1.373(5) . ? C1 C15 1.405(5) . ? C2 C3 1.396(6) . ? C3 N4 1.318(6) . ? N4 C16 1.364(5) . ? C5 C6 1.343(6) . ? C5 C16 1.431(6) . ? C6 C18 1.429(6) . ? C7 C8 1.345(6) . ? C7 C18 1.419(6) . ? C8 C20 1.414(6) . ? C9 C10 1.340(6) . ? C9 C20 1.430(6) . ? C10 C22 1.415(5) . ? N11 C12 1.313(5) . ? N11 C22 1.360(5) . ? C12 C13 1.392(5) . ? C13 C14 1.362(5) . ? C14 C21 1.406(5) . ? C15 C16 1.406(5) . ? C15 C17 1.456(5) . ? C17 C18 1.411(5) . ? C17 C19 1.442(5) . ? C19 C20 1.411(5) . ? C19 C21 1.442(5) . ? C21 C22 1.421(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C15 119.8(3) . . ? C1 C2 C3 118.9(4) . . ? N4 C3 C2 123.5(4) . . ? C3 N4 C16 117.1(3) . . ? C6 C5 C16 119.5(4) . . ? C5 C6 C18 122.6(4) . . ? C8 C7 C18 120.5(4) . . ? C7 C8 C20 120.8(4) . . ? C10 C9 C20 121.7(4) . . ? C9 C10 C22 120.1(4) . . ? C12 N11 C22 117.8(3) . . ? N11 C12 C13 123.3(4) . . ? C14 C13 C12 119.6(4) . . ? C13 C14 C21 119.7(3) . . ? C1 C15 C16 116.3(3) . . ? C1 C15 C17 123.4(3) . . ? C16 C15 C17 119.9(3) . . ? N4 C16 C15 123.7(4) . . ? N4 C16 C5 116.4(4) . . ? C15 C16 C5 119.7(4) . . ? C18 C17 C19 118.1(3) . . ? C18 C17 C15 117.2(3) . . ? C19 C17 C15 124.6(3) . . ? C17 C18 C7 120.0(4) . . ? C17 C18 C6 119.3(4) . . ? C7 C18 C6 120.7(4) . . ? C20 C19 C17 117.8(3) . . ? C20 C19 C21 117.5(3) . . ? C17 C19 C21 124.4(3) . . ? C19 C20 C8 120.1(4) . . ? C19 C20 C9 119.5(4) . . ? C8 C20 C9 120.3(4) . . ? C14 C21 C22 116.2(3) . . ? C14 C21 C19 124.1(3) . . ? C22 C21 C19 119.2(3) . . ? N11 C22 C10 117.1(3) . . ? N11 C22 C21 122.9(3) . . ? C10 C22 C21 119.9(3) . . ? ## END data_2-I _database_code_depnum_ccdc_archive 'CCDC 686816' _audit_creation_date 2007-12-29T18:04:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H12 N2' _chemical_formula_weight 280.32 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 18.4176(19) _cell_length_b 13.8286(14) _cell_length_c 11.2744(12) _cell_angle_alpha 90.000 _cell_angle_beta 107.010(2) _cell_angle_gamma 90.000 _cell_volume 2745.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5344 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.3 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_unetI/netI 0.0432 _diffrn_reflns_number 30420 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 31.98 _diffrn_reflns_theta_full 31.98 _diffrn_measured_fraction_theta_full 0.937 _diffrn_measured_fraction_theta_max 0.937 _reflns_number_total 8931 _reflns_number_gt 4781 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0610P)^2^+0.3348P] 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_number_reflns 8931 _refine_ls_number_parameters 493 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1075 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1489 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.003 _refine_diff_density_max 0.218 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # 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 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' N N 0.0061 0.0033 '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 C1 C -0.10720(9) -0.82945(11) 0.48243(15) 0.0499(4) Uani 1 1 d . . . C2 C -0.13422(10) -0.91634(14) 0.42884(18) 0.0619(4) Uani 1 1 d . . . C3 C -0.17335(10) -0.92091(17) 0.30254(19) 0.0684(5) Uani 1 1 d . . . C4 C -0.18830(10) -0.83840(17) 0.23476(18) 0.0683(5) Uani 1 1 d . . . C16 C -0.16535(9) -0.74728(14) 0.28916(15) 0.0578(4) Uani 1 1 d . . . C15 C -0.11944(8) -0.74286(11) 0.41413(14) 0.0477(3) Uani 1 1 d . . . C6 C -0.17995(10) -0.58340(19) 0.2768(2) 0.0765(6) Uani 1 1 d . . . C18 C -0.13468(9) -0.56870(13) 0.40213(18) 0.0611(5) Uani 1 1 d . . . C17 C -0.09521(8) -0.64835(11) 0.46787(15) 0.0485(4) Uani 1 1 d . . . C7 C -0.13013(11) -0.47652(14) 0.4592(2) 0.0724(6) Uani 1 1 d . . . C8 C -0.08878(11) -0.46436(13) 0.5783(2) 0.0704(5) Uani 1 1 d . . . C20 C -0.04088(9) -0.53931(11) 0.64148(17) 0.0563(4) Uani 1 1 d . . . C19 C -0.03816(8) -0.62897(10) 0.58381(14) 0.0448(3) Uani 1 1 d . . . C9 C 0.00762(11) -0.52514(14) 0.76525(19) 0.0652(5) Uani 1 1 d . . . C22 C 0.07488(9) -0.66116(11) 0.76029(14) 0.0482(3) Uani 1 1 d . . . C21 C 0.02775(8) -0.68845(10) 0.64146(13) 0.0413(3) Uani 1 1 d . . . C11 C 0.14284(9) -0.71118(13) 0.81531(15) 0.0540(4) Uani 1 1 d . . . C12 C 0.16645(9) -0.78318(12) 0.75320(15) 0.0528(4) Uani 1 1 d . . . C13 C 0.12267(9) -0.80788(11) 0.63406(15) 0.0477(3) Uani 1 1 d . . . C14 C 0.05485(8) -0.76229(10) 0.57973(14) 0.0433(3) Uani 1 1 d . . . C101 C -0.55076(8) -0.24072(10) 0.02688(13) 0.0422(3) Uani 1 1 d . . . C102 C -0.61727(9) -0.19199(11) 0.01522(15) 0.0478(3) Uani 1 1 d . . . C103 C -0.66262(9) -0.21505(13) 0.09085(15) 0.0546(4) Uani 1 1 d . . . C104 C -0.64155(9) -0.28773(13) 0.17481(16) 0.0551(4) Uani 1 1 d . . . C116 C -0.57454(9) -0.34017(11) 0.18688(13) 0.0472(3) Uani 1 1 d . . . C115 C -0.52603(8) -0.31536(10) 0.11457(12) 0.0402(3) Uani 1 1 d . . . C106 C -0.50994(11) -0.47828(13) 0.25800(16) 0.0615(5) Uani 1 1 d . . . C118 C -0.45960(9) -0.46558(11) 0.18305(14) 0.0506(4) Uani 1 1 d . . . C117 C -0.46057(8) -0.37670(10) 0.12258(12) 0.0416(3) Uani 1 1 d . . . C107 C -0.41163(10) -0.54184(12) 0.16997(17) 0.0604(5) Uani 1 1 d . . . C108 C -0.36792(10) -0.53230(12) 0.09363(18) 0.0610(5) Uani 1 1 d . . . C120 C -0.36212(8) -0.44080(11) 0.03942(15) 0.0512(4) Uani 1 1 d . . . C119 C -0.40199(8) -0.35999(10) 0.06344(13) 0.0423(3) Uani 1 1 d . . . C109 C -0.31563(9) -0.42941(15) -0.04091(18) 0.0619(5) Uani 1 1 d . . . C122 C -0.33050(8) -0.26510(12) -0.04855(14) 0.0507(4) Uani 1 1 d . . . C121 C -0.37674(8) -0.26687(10) 0.03158(13) 0.0427(3) Uani 1 1 d . . . C111 C -0.30682(10) -0.17554(14) -0.08400(17) 0.0612(5) Uani 1 1 d . . . C112 C -0.32245(10) -0.09189(15) -0.03425(18) 0.0637(5) Uani 1 1 d . . . C113 C -0.36185(9) -0.09297(12) 0.05476(18) 0.0572(4) Uani 1 1 d . . . C114 C -0.38897(8) -0.17875(10) 0.08596(15) 0.0475(3) Uani 1 1 d . . . N5 N -0.19271(8) -0.66564(15) 0.21915(15) 0.0755(5) Uani 1 1 d . . . N10 N 0.06069(9) -0.58213(11) 0.82536(14) 0.0634(4) Uani 1 1 d . . . N105 N -0.56244(8) -0.41930(11) 0.26550(13) 0.0602(4) Uani 1 1 d . . . N110 N -0.30309(8) -0.34826(12) -0.08951(14) 0.0631(4) Uani 1 1 d . . . H1 H -0.0820(9) -0.8260(10) 0.5699(15) 0.048(4) Uiso 1 1 d . . . H2 H -0.1246(12) -0.9796(16) 0.479(2) 0.096(7) Uiso 1 1 d . . . H3 H -0.1931(12) -0.9824(16) 0.265(2) 0.088(7) Uiso 1 1 d . . . H4 H -0.2156(12) -0.8391(13) 0.152(2) 0.075(6) Uiso 1 1 d . . . H6 H -0.2009(11) -0.5248(15) 0.2340(19) 0.084(6) Uiso 1 1 d . . . H7 H -0.1590(11) -0.4292(15) 0.4051(19) 0.085(6) Uiso 1 1 d . . . H8 H -0.0841(12) -0.4024(16) 0.6262(19) 0.088(6) Uiso 1 1 d . . . H9 H -0.0013(10) -0.4664(14) 0.8056(18) 0.077(6) Uiso 1 1 d . . . H11 H 0.1718(10) -0.6908(12) 0.8979(17) 0.059(5) Uiso 1 1 d . . . H12 H 0.2137(12) -0.8153(13) 0.7926(18) 0.074(6) Uiso 1 1 d . . . H13 H 0.1399(9) -0.8570(11) 0.5877(15) 0.055(4) Uiso 1 1 d . . . H14 H 0.0272(9) -0.7786(11) 0.4990(15) 0.049(4) Uiso 1 1 d . . . H101 H -0.5208(9) -0.2271(10) -0.0294(15) 0.049(4) Uiso 1 1 d . . . H102 H -0.6316(9) -0.1407(11) -0.0484(16) 0.054(4) Uiso 1 1 d . . . H103 H -0.7089(11) -0.1788(12) 0.0853(16) 0.061(5) Uiso 1 1 d . . . H104 H -0.6716(12) -0.3072(14) 0.2288(19) 0.080(6) Uiso 1 1 d . . . H106 H -0.5012(10) -0.5336(13) 0.3084(18) 0.071(5) Uiso 1 1 d . . . H107 H -0.4133(10) -0.6018(13) 0.2130(16) 0.065(5) Uiso 1 1 d . . . H108 H -0.3364(10) -0.5807(13) 0.0743(17) 0.066(5) Uiso 1 1 d . . . H109 H -0.2941(11) -0.4861(14) -0.0642(18) 0.077(6) Uiso 1 1 d . . . H111 H -0.2753(12) -0.1776(13) -0.1446(19) 0.081(6) Uiso 1 1 d . . . H112 H -0.3077(10) -0.0309(13) -0.0546(17) 0.071(6) Uiso 1 1 d . . . H113 H -0.3722(10) -0.0318(13) 0.0968(17) 0.067(5) Uiso 1 1 d . . . H114 H -0.4151(9) -0.1808(10) 0.1494(14) 0.046(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 C1 0.0447(8) 0.0551(9) 0.0474(9) -0.0002(7) 0.0095(7) 0.0014(7) C2 0.0544(9) 0.0613(11) 0.0669(11) -0.0068(9) 0.0131(8) -0.0004(8) C3 0.0488(9) 0.0838(14) 0.0692(12) -0.0212(11) 0.0120(9) 0.0012(9) C4 0.0403(9) 0.1133(17) 0.0482(10) -0.0130(10) 0.0081(7) 0.0016(9) C16 0.0331(7) 0.0915(13) 0.0494(9) 0.0114(8) 0.0130(6) 0.0058(7) C15 0.0328(7) 0.0656(10) 0.0465(8) 0.0055(7) 0.0145(6) 0.0055(6) C6 0.0423(9) 0.0931(16) 0.0912(15) 0.0466(13) 0.0149(9) 0.0099(10) C18 0.0376(8) 0.0681(11) 0.0819(12) 0.0297(9) 0.0240(8) 0.0111(7) C17 0.0367(7) 0.0558(9) 0.0579(9) 0.0144(7) 0.0215(7) 0.0087(6) C7 0.0515(10) 0.0577(11) 0.1186(18) 0.0348(11) 0.0414(12) 0.0191(8) C8 0.0649(11) 0.0497(10) 0.1107(17) 0.0071(11) 0.0480(12) 0.0114(9) C20 0.0559(9) 0.0457(8) 0.0800(12) 0.0002(8) 0.0399(9) 0.0030(7) C19 0.0426(7) 0.0453(8) 0.0529(8) 0.0053(6) 0.0237(6) 0.0033(6) C9 0.0762(12) 0.0533(10) 0.0779(13) -0.0205(9) 0.0411(11) -0.0085(9) C22 0.0523(8) 0.0509(8) 0.0456(8) -0.0039(6) 0.0208(7) -0.0073(7) C21 0.0420(7) 0.0425(7) 0.0426(7) 0.0013(6) 0.0176(6) -0.0013(6) C11 0.0497(9) 0.0650(10) 0.0428(8) 0.0012(7) 0.0066(7) -0.0090(8) C12 0.0433(8) 0.0594(10) 0.0515(9) 0.0091(7) 0.0074(7) 0.0030(7) C13 0.0449(8) 0.0478(8) 0.0520(9) 0.0022(7) 0.0169(7) 0.0046(6) C14 0.0408(7) 0.0479(8) 0.0405(7) -0.0018(6) 0.0109(6) 0.0020(6) C101 0.0396(7) 0.0464(8) 0.0403(7) 0.0014(6) 0.0114(6) -0.0020(6) C102 0.0433(8) 0.0498(8) 0.0477(8) -0.0004(7) 0.0090(6) 0.0024(6) C103 0.0422(8) 0.0680(11) 0.0541(9) -0.0084(8) 0.0148(7) 0.0040(8) C104 0.0479(9) 0.0718(11) 0.0500(9) -0.0054(8) 0.0214(7) -0.0089(8) C116 0.0483(8) 0.0544(9) 0.0386(7) -0.0002(6) 0.0122(6) -0.0104(7) C115 0.0389(7) 0.0430(7) 0.0366(7) -0.0021(5) 0.0079(5) -0.0054(5) C106 0.0735(12) 0.0537(10) 0.0524(10) 0.0162(8) 0.0106(9) -0.0114(9) C118 0.0503(8) 0.0465(8) 0.0467(8) 0.0049(6) 0.0011(7) -0.0039(7) C117 0.0399(7) 0.0417(7) 0.0384(7) -0.0001(5) 0.0040(6) -0.0021(6) C107 0.0612(10) 0.0444(9) 0.0630(11) 0.0061(8) -0.0015(9) 0.0027(7) C108 0.0502(9) 0.0459(9) 0.0721(11) -0.0103(8) -0.0054(8) 0.0092(7) C120 0.0373(7) 0.0521(9) 0.0566(9) -0.0124(7) 0.0019(7) 0.0006(6) C119 0.0364(7) 0.0456(8) 0.0403(7) -0.0033(6) 0.0039(6) 0.0008(6) C109 0.0410(8) 0.0652(11) 0.0768(12) -0.0259(10) 0.0130(8) -0.0003(8) C122 0.0344(7) 0.0674(10) 0.0484(8) -0.0058(7) 0.0089(6) -0.0040(7) C121 0.0320(6) 0.0510(8) 0.0424(7) -0.0004(6) 0.0065(6) -0.0015(6) C111 0.0440(9) 0.0829(13) 0.0597(10) 0.0069(9) 0.0198(8) -0.0087(8) C112 0.0490(9) 0.0634(11) 0.0791(12) 0.0185(10) 0.0194(9) -0.0053(8) C113 0.0473(8) 0.0499(9) 0.0743(11) 0.0055(8) 0.0174(8) -0.0004(7) C114 0.0423(8) 0.0467(8) 0.0542(9) 0.0009(7) 0.0154(7) -0.0007(6) N5 0.0471(8) 0.1116(15) 0.0624(10) 0.0319(10) 0.0078(7) 0.0055(9) N10 0.0722(9) 0.0605(9) 0.0626(9) -0.0164(7) 0.0278(8) -0.0058(8) N105 0.0651(9) 0.0639(9) 0.0531(8) 0.0103(7) 0.0195(7) -0.0098(7) N110 0.0436(7) 0.0825(11) 0.0654(9) -0.0230(8) 0.0196(7) -0.0062(7) #----------------------------------------------------------------------------# # 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 C1 C2 1.371(2) . ? C1 C15 1.406(2) . ? C2 C3 1.397(3) . ? C3 C4 1.356(3) . ? C4 C16 1.411(3) . ? C16 N5 1.385(2) . ? C16 C15 1.417(2) . ? C15 C17 1.455(2) . ? C6 N5 1.297(3) . ? C6 C18 1.430(3) . ? C18 C17 1.406(2) . ? C18 C7 1.420(3) . ? C17 C19 1.443(2) . ? C7 C8 1.346(3) . ? C8 C20 1.411(2) . ? C20 C19 1.408(2) . ? C20 C9 1.433(3) . ? C19 C21 1.453(2) . ? C9 N10 1.284(2) . ? C22 N10 1.383(2) . ? C22 C11 1.406(2) . ? C22 C21 1.418(2) . ? C21 C14 1.407(2) . ? C11 C12 1.360(2) . ? C12 C13 1.392(2) . ? C13 C14 1.373(2) . ? C101 C102 1.370(2) . ? C101 C115 1.4096(19) . ? C102 C103 1.394(2) . ? C103 C104 1.357(3) . ? C104 C116 1.403(2) . ? C116 N105 1.385(2) . ? C116 C115 1.417(2) . ? C115 C117 1.455(2) . ? C106 N105 1.287(2) . ? C106 C118 1.436(3) . ? C118 C117 1.403(2) . ? C118 C107 1.411(2) . ? C117 C119 1.443(2) . ? C107 C108 1.346(3) . ? C108 C120 1.423(2) . ? C120 C119 1.406(2) . ? C120 C109 1.425(3) . ? C119 C121 1.450(2) . ? C109 N110 1.299(2) . ? C122 N110 1.388(2) . ? C122 C111 1.409(2) . ? C122 C121 1.411(2) . ? C121 C114 1.412(2) . ? C111 C112 1.353(3) . ? C112 C113 1.400(3) . ? C113 C114 1.372(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 C2 C1 C15 121.71(16) . . ? C1 C2 C3 120.10(19) . . ? C4 C3 C2 119.71(19) . . ? C3 C4 C16 121.39(17) . . ? N5 C16 C4 117.86(17) . . ? N5 C16 C15 122.91(17) . . ? C4 C16 C15 119.12(16) . . ? C1 C15 C16 117.48(15) . . ? C1 C15 C17 123.82(14) . . ? C16 C15 C17 118.31(14) . . ? N5 C6 C18 126.00(18) . . ? C17 C18 C7 120.78(18) . . ? C17 C18 C6 118.15(18) . . ? C7 C18 C6 121.07(17) . . ? C18 C17 C19 117.35(15) . . ? C18 C17 C15 115.85(15) . . ? C19 C17 C15 126.71(13) . . ? C8 C7 C18 120.37(17) . . ? C7 C8 C20 119.94(19) . . ? C19 C20 C8 121.02(18) . . ? C19 C20 C9 118.29(15) . . ? C8 C20 C9 120.68(17) . . ? C20 C19 C17 117.86(14) . . ? C20 C19 C21 115.47(14) . . ? C17 C19 C21 126.29(13) . . ? N10 C9 C20 126.26(16) . . ? N10 C22 C11 115.90(14) . . ? N10 C22 C21 123.58(14) . . ? C11 C22 C21 120.40(14) . . ? C14 C21 C22 116.93(13) . . ? C14 C21 C19 124.09(13) . . ? C22 C21 C19 118.19(13) . . ? C12 C11 C22 120.71(15) . . ? C11 C12 C13 119.63(15) . . ? C14 C13 C12 120.83(15) . . ? C13 C14 C21 121.38(14) . . ? C102 C101 C115 121.58(14) . . ? C101 C102 C103 120.50(15) . . ? C104 C103 C102 119.74(15) . . ? C103 C104 C116 120.94(15) . . ? N105 C116 C104 116.28(14) . . ? N105 C116 C115 123.32(14) . . ? C104 C116 C115 120.26(14) . . ? C101 C115 C116 116.89(13) . . ? C101 C115 C117 124.21(13) . . ? C116 C115 C117 118.27(13) . . ? N105 C106 C118 126.02(15) . . ? C117 C118 C107 121.56(16) . . ? C117 C118 C106 118.31(15) . . ? C107 C118 C106 120.12(15) . . ? C118 C117 C119 117.37(13) . . ? C118 C117 C115 115.68(13) . . ? C119 C117 C115 126.57(12) . . ? C108 C107 C118 120.23(16) . . ? C107 C108 C120 119.73(16) . . ? C119 C120 C108 120.99(16) . . ? C119 C120 C109 118.63(15) . . ? C108 C120 C109 120.38(16) . . ? C120 C119 C117 117.70(13) . . ? C120 C119 C121 115.76(14) . . ? C117 C119 C121 126.45(13) . . ? N110 C109 C120 125.28(16) . . ? N110 C122 C111 117.44(16) . . ? N110 C122 C121 123.02(15) . . ? C111 C122 C121 119.44(15) . . ? C114 C121 C122 117.77(14) . . ? C114 C121 C119 123.76(14) . . ? C122 C121 C119 118.13(13) . . ? C112 C111 C122 120.85(17) . . ? C111 C112 C113 120.39(17) . . ? C114 C113 C112 119.79(17) . . ? C113 C114 C121 121.24(16) . . ? C6 N5 C16 116.55(17) . . ? C9 N10 C22 115.97(15) . . ? C106 N105 C116 116.24(14) . . ? C109 N110 C122 116.65(15) . . ? ##END data_2-II _database_code_depnum_ccdc_archive 'CCDC 686817' _audit_creation_date 2007-12-29T18:29:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H12 N2' _chemical_formula_weight 280.32 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 20.3520(6) _cell_length_b 9.0912(3) _cell_length_c 7.5400(2) _cell_angle_alpha 90 _cell_angle_beta 92.2800(10) _cell_angle_gamma 90 _cell_volume 1393.98(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1852 _cell_measurement_theta_max 23.7 _cell_measurement_theta_min 2.5 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_unetI/netI 0.0574 _diffrn_reflns_number 14182 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2 _diffrn_reflns_theta_max 32.81 _diffrn_reflns_theta_full 32.81 _diffrn_measured_fraction_theta_full 0.945 _diffrn_measured_fraction_theta_max 0.945 _reflns_number_total 2434 _reflns_number_gt 1163 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0550P)^2^+1.2465P] 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_number_reflns 2434 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.151 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1768 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_restrained_S_all 1.01 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.306 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.044 #----------------------------------------------------------------------------# # 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 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' N N 0.0061 0.0033 '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 C1 C 0.43753(8) 0.3661(2) 0.3458(2) 0.0380(4) Uani 1 1 d . . . H1 H 0.4803 0.3785 0.3915 0.046 Uiso 1 1 calc R . . C2 C 0.39238(9) 0.4744(2) 0.3701(3) 0.0487(5) Uani 1 1 d . . . H2 H 0.4047 0.5584 0.4334 0.058 Uiso 1 1 calc R . . C3 C 0.32790(10) 0.4607(3) 0.3011(3) 0.0616(6) Uani 1 1 d . . . H3 H 0.2979 0.5368 0.3141 0.074 Uiso 1 1 calc R . . C4 C 0.30958(9) 0.3355(3) 0.2150(3) 0.0605(6) Uani 1 1 d . . . H4 H 0.2667 0.3261 0.1693 0.073 Uiso 1 1 calc R . . C6 C 0.36699(12) -0.0239(3) 0.1327(3) 0.0617(6) Uani 1 1 d . . . H6 H 0.3491 -0.1135 0.0964 0.074 Uiso 1 1 calc R . . C7 C 0.46845(12) -0.1586(2) 0.2176(3) 0.0609(6) Uani 1 1 d . . . H7 H 0.4477 -0.2469 0.1883 0.073 Uiso 1 1 calc R . . C15 C 0.42084(8) 0.2362(2) 0.2531(2) 0.0364(4) Uani 1 1 d . . . C16 C 0.35410(9) 0.2197(2) 0.1935(3) 0.0471(5) Uani 1 1 d . . . C17 C 0.46458(8) 0.11180(19) 0.2342(2) 0.0369(4) Uani 1 1 d . . . C18 C 0.43424(11) -0.0241(2) 0.1946(3) 0.0477(5) Uani 1 1 d . . . N5 N 0.32885(9) 0.0896(3) 0.1227(3) 0.0629(6) 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 C1 0.0274(8) 0.0455(10) 0.0411(10) -0.0009(8) 0.0000(7) -0.0012(7) C2 0.0393(10) 0.0519(12) 0.0551(12) -0.0052(10) 0.0050(9) 0.0089(9) C3 0.0365(10) 0.0780(16) 0.0705(16) -0.0007(13) 0.0033(10) 0.0173(11) C4 0.0251(9) 0.0935(18) 0.0626(14) 0.0006(13) -0.0005(9) 0.0016(11) C6 0.0641(14) 0.0688(15) 0.0526(13) -0.0114(12) 0.0089(11) -0.0327(13) C7 0.0972(18) 0.0385(11) 0.0478(12) -0.0044(9) 0.0142(12) -0.0120(11) C15 0.0266(8) 0.0475(10) 0.0352(9) 0.0029(8) 0.0017(6) -0.0030(7) C16 0.0316(9) 0.0666(14) 0.0431(10) 0.0013(9) 0.0006(8) -0.0124(9) C17 0.0397(9) 0.0410(10) 0.0301(9) -0.0003(7) 0.0027(7) -0.0051(8) C18 0.0604(12) 0.0455(11) 0.0378(10) -0.0046(9) 0.0088(9) -0.0146(10) N5 0.0432(10) 0.0846(15) 0.0608(12) -0.0105(11) -0.0003(9) -0.0259(10) #----------------------------------------------------------------------------# # 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 C1 C2 1.364(2) . ? C1 C15 1.408(2) . ? C2 C3 1.398(3) . ? C3 C4 1.356(3) . ? C4 C16 1.403(3) . ? C6 N5 1.291(3) . ? C6 C18 1.428(3) . ? C7 C7 1.356(5) 2_655 ? C7 C18 1.414(3) . ? C15 C16 1.421(2) . ? C15 C17 1.450(2) . ? C16 N5 1.388(3) . ? C17 C18 1.408(2) . ? C17 C17 1.452(3) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C15 121.46(17) . . ? C1 C2 C3 120.9(2) . . ? C4 C3 C2 119.3(2) . . ? C3 C4 C16 121.28(19) . . ? N5 C6 C18 125.9(2) . . ? C7 C7 C18 119.93(13) 2_655 . ? C1 C15 C16 117.00(17) . . ? C1 C15 C17 124.50(15) . . ? C16 C15 C17 118.02(17) . . ? N5 C16 C4 116.94(18) . . ? N5 C16 C15 123.08(19) . . ? C4 C16 C15 119.87(19) . . ? C18 C17 C15 116.06(16) . . ? C18 C17 C17 117.34(12) . 2_655 ? C15 C17 C17 126.42(10) . 2_655 ? C17 C18 C7 121.5(2) . . ? C17 C18 C6 118.3(2) . . ? C7 C18 C6 120.1(2) . . ? C6 N5 C16 116.47(18) . . ? ##END data_2-III _database_code_depnum_ccdc_archive 'CCDC 686818' _audit_creation_date 2007-12-29T18:25:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H12 N2' _chemical_formula_weight 280.32 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 16.0623(11) _cell_length_b 7.8336(5) _cell_length_c 21.4841(14) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 2703.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7621 _cell_measurement_theta_max 26.9 _cell_measurement_theta_min 3.05 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_unetI/netI 0.0176 _diffrn_reflns_number 23933 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 29.91 _diffrn_reflns_theta_full 29.91 _diffrn_measured_fraction_theta_full 0.956 _diffrn_measured_fraction_theta_max 0.956 _reflns_number_total 3731 _reflns_number_gt 2756 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0559P)^2^+0.4771P] 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_number_reflns 3731 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.2 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.031 #----------------------------------------------------------------------------# # 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 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' N N 0.0061 0.0033 '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 C1 C -0.03036(7) 0.26587(16) -0.14597(5) 0.0442(3) Uani 1 1 d . . . C2 C -0.03282(8) 0.42975(17) -0.16786(6) 0.0511(3) Uani 1 1 d . . . C3 C 0.04097(9) 0.51793(19) -0.18091(6) 0.0549(3) Uani 1 1 d . . . C4 C 0.11589(8) 0.44040(18) -0.17074(6) 0.0532(3) Uani 1 1 d . . . C16 C 0.12002(7) 0.27516(17) -0.14575(5) 0.0457(3) Uani 1 1 d . . . C15 C 0.04588(6) 0.18078(15) -0.13437(5) 0.0405(2) Uani 1 1 d . . . C6 C 0.20100(7) 0.08351(18) -0.09383(6) 0.0523(3) Uani 1 1 d . . . C18 C 0.13079(7) -0.01865(15) -0.07612(5) 0.0451(3) Uani 1 1 d . . . C17 C 0.05262(6) 0.01695(15) -0.10329(5) 0.0399(2) Uani 1 1 d . . . C7 C 0.14071(8) -0.14831(18) -0.03073(6) 0.0520(3) Uani 1 1 d . . . C8 C 0.07344(9) -0.23518(17) -0.01053(6) 0.0521(3) Uani 1 1 d . . . C20 C -0.00471(8) -0.21474(15) -0.04100(5) 0.0457(3) Uani 1 1 d . . . C19 C -0.01409(7) -0.10269(14) -0.09139(5) 0.0404(2) Uani 1 1 d . . . C9 C -0.07542(9) -0.31072(17) -0.02057(6) 0.0530(3) Uani 1 1 d . . . C22 C -0.15224(7) -0.23361(15) -0.10517(6) 0.0483(3) Uani 1 1 d . . . C21 C -0.08828(6) -0.12828(15) -0.12927(5) 0.0420(2) Uani 1 1 d . . . C11 C -0.22336(8) -0.26810(19) -0.14173(8) 0.0597(3) Uani 1 1 d . . . C12 C -0.22924(8) -0.21024(19) -0.20141(8) 0.0628(4) Uani 1 1 d . . . C13 C -0.16417(8) -0.11539(18) -0.22716(7) 0.0555(3) Uani 1 1 d . . . C14 C -0.09568(7) -0.07419(16) -0.19181(6) 0.0468(3) Uani 1 1 d . . . N5 N 0.19856(6) 0.21758(15) -0.12875(5) 0.0537(3) Uani 1 1 d . . . N10 N -0.14712(7) -0.31608(14) -0.04833(5) 0.0564(3) Uani 1 1 d . . . H1 H -0.0824(8) 0.2063(17) -0.1351(6) 0.046(3) Uiso 1 1 d . . . H2 H -0.0869(9) 0.4855(19) -0.1746(6) 0.058(4) Uiso 1 1 d . . . H3 H 0.0379(8) 0.635(2) -0.1972(7) 0.064(4) Uiso 1 1 d . . . H4 H 0.1684(10) 0.501(2) -0.1797(7) 0.068(4) Uiso 1 1 d . . . H8 H 0.2547(9) 0.0437(18) -0.0780(6) 0.061(4) Uiso 1 1 d . . . H11 H 0.1968(10) -0.168(2) -0.0133(7) 0.067(4) Uiso 1 1 d . . . H12 H 0.0776(9) -0.315(2) 0.0220(7) 0.063(4) Uiso 1 1 d . . . H15 H -0.0685(9) -0.376(2) 0.0177(7) 0.062(4) Uiso 1 1 d . . . H19 H -0.2645(10) -0.346(2) -0.1225(7) 0.069(4) Uiso 1 1 d . . . H20 H -0.2777(9) -0.241(2) -0.2274(8) 0.077(5) Uiso 1 1 d . . . H21 H -0.1661(9) -0.079(2) -0.2717(7) 0.065(4) Uiso 1 1 d . . . H22 H -0.0497(8) -0.0058(18) -0.2108(6) 0.053(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 C1 0.0369(5) 0.0511(7) 0.0446(6) -0.0028(5) 0.0018(4) 0.0031(5) C2 0.0504(7) 0.0537(7) 0.0492(6) -0.0002(5) -0.0013(5) 0.0083(6) C3 0.0644(8) 0.0491(7) 0.0511(7) 0.0015(6) -0.0015(6) -0.0025(6) C4 0.0522(7) 0.0576(8) 0.0498(6) -0.0015(6) 0.0014(5) -0.0121(6) C16 0.0380(6) 0.0548(7) 0.0441(6) -0.0074(5) 0.0022(4) -0.0026(5) C15 0.0352(5) 0.0470(6) 0.0392(5) -0.0064(4) 0.0022(4) 0.0007(4) C6 0.0330(5) 0.0611(8) 0.0627(7) -0.0115(6) -0.0032(5) 0.0055(5) C18 0.0373(5) 0.0506(6) 0.0474(6) -0.0095(5) -0.0008(4) 0.0076(5) C17 0.0339(5) 0.0460(6) 0.0399(5) -0.0066(4) 0.0030(4) 0.0046(4) C7 0.0477(6) 0.0567(7) 0.0517(7) -0.0066(6) -0.0072(5) 0.0143(6) C8 0.0624(8) 0.0500(7) 0.0440(6) -0.0022(5) -0.0045(5) 0.0106(6) C20 0.0505(6) 0.0443(6) 0.0422(6) -0.0061(5) 0.0032(5) 0.0046(5) C19 0.0377(5) 0.0430(6) 0.0405(5) -0.0065(4) 0.0040(4) 0.0043(4) C9 0.0652(8) 0.0477(7) 0.0461(6) -0.0012(5) 0.0068(6) -0.0028(6) C22 0.0424(6) 0.0456(6) 0.0570(7) -0.0055(5) 0.0072(5) -0.0010(5) C21 0.0358(5) 0.0430(6) 0.0472(6) -0.0065(5) 0.0036(4) 0.0027(4) C11 0.0420(6) 0.0547(8) 0.0823(10) -0.0022(7) 0.0004(6) -0.0077(6) C12 0.0469(7) 0.0612(8) 0.0805(10) -0.0053(7) -0.0161(6) -0.0041(6) C13 0.0516(7) 0.0596(8) 0.0554(7) -0.0046(6) -0.0088(6) 0.0035(6) C14 0.0397(5) 0.0531(7) 0.0475(6) -0.0049(5) 0.0017(5) 0.0019(5) N5 0.0357(5) 0.0624(7) 0.0631(6) -0.0074(5) 0.0015(4) -0.0026(5) N10 0.0578(6) 0.0523(6) 0.0590(6) -0.0012(5) 0.0105(5) -0.0085(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 C1 C2 1.3678(18) . ? C1 C15 1.4163(15) . ? C2 C3 1.4002(19) . ? C3 C4 1.3655(19) . ? C4 C16 1.4029(19) . ? C16 N5 1.3886(15) . ? C16 C15 1.4229(16) . ? C15 C17 1.4507(17) . ? C6 N5 1.2913(18) . ? C6 C18 1.4343(17) . ? C18 C17 1.4124(14) . ? C18 C7 1.4170(18) . ? C17 C19 1.4463(16) . ? C7 C8 1.349(2) . ? C8 C20 1.4246(18) . ? C20 C19 1.4019(16) . ? C20 C9 1.4311(18) . ? C19 C21 1.4568(15) . ? C9 N10 1.2976(18) . ? C22 N10 1.3840(17) . ? C22 C11 1.4124(18) . ? C22 C21 1.4157(16) . ? C21 C14 1.4138(16) . ? C11 C12 1.363(2) . ? C12 C13 1.397(2) . ? C13 C14 1.3752(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 C2 C1 C15 121.81(11) . . ? C1 C2 C3 120.50(12) . . ? C4 C3 C2 119.63(13) . . ? C3 C4 C16 120.88(12) . . ? N5 C16 C4 116.32(11) . . ? N5 C16 C15 123.11(12) . . ? C4 C16 C15 120.37(11) . . ? C1 C15 C16 116.67(11) . . ? C1 C15 C17 124.19(10) . . ? C16 C15 C17 118.44(10) . . ? N5 C6 C18 125.74(11) . . ? C17 C18 C7 121.73(11) . . ? C17 C18 C6 118.63(11) . . ? C7 C18 C6 119.61(11) . . ? C18 C17 C19 117.23(10) . . ? C18 C17 C15 115.55(10) . . ? C19 C17 C15 126.82(9) . . ? C8 C7 C18 119.53(11) . . ? C7 C8 C20 120.09(12) . . ? C19 C20 C8 121.33(11) . . ? C19 C20 C9 118.72(11) . . ? C8 C20 C9 119.95(12) . . ? C20 C19 C17 117.55(10) . . ? C20 C19 C21 115.67(10) . . ? C17 C19 C21 126.62(10) . . ? N10 C9 C20 125.48(12) . . ? N10 C22 C11 116.71(12) . . ? N10 C22 C21 123.47(11) . . ? C11 C22 C21 119.68(12) . . ? C14 C21 C22 117.46(11) . . ? C14 C21 C19 123.94(10) . . ? C22 C21 C19 118.01(11) . . ? C12 C11 C22 121.03(13) . . ? C11 C12 C13 119.84(13) . . ? C14 C13 C12 120.31(13) . . ? C13 C14 C21 121.45(12) . . ? C6 N5 C16 116.40(11) . . ? C9 N10 C22 116.30(11) . . ? ##END data_3 _database_code_depnum_ccdc_archive 'CCDC 686819' _audit_creation_date 2007-12-29T18:39:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H12 N2' _chemical_formula_weight 280.32 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 13.9335(19) _cell_length_b 5.8691(10) _cell_length_c 17.354(2) _cell_angle_alpha 90 _cell_angle_beta 104.734(3) _cell_angle_gamma 90 _cell_volume 1372.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_max 22.2 _cell_measurement_theta_min 3. _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_unetI/netI 0.0264 _diffrn_reflns_number 8304 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 23.28 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1986 _reflns_number_gt 1454 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0557P)^2^+0.6722P] 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_number_reflns 1986 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1353 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.154 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # 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 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' N N 0.0061 0.0033 '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 C1 C 0.44619(15) 0.3189(4) 0.88177(14) 0.0594(8) Uani 0.23(2) 1 d P A 1 H1 H 0.4776 0.4577 0.8798 0.071 Uiso 0.23(2) 1 calc PR A 1 C2 C 0.4179(2) 0.2579(6) 0.94672(18) 0.0698(8) Uani 1 1 d . A 1 H2 H 0.4293 0.3594 0.9892 0.084 Uiso 1 1 calc R A 1 C3 C 0.3728(2) 0.0530(6) 0.9545(2) 0.0818(10) Uani 1 1 d . A 1 H3 H 0.3578 0.0138 1.002 0.098 Uiso 1 1 calc R A 1 C4 C 0.3512(2) -0.0880(6) 0.8918(3) 0.0821(10) Uani 1 1 d . A 1 H4 H 0.3199 -0.2259 0.8957 0.099 Uiso 1 1 calc R A 1 C5 C 0.3409(2) -0.1593(7) 0.7507(3) 0.0928(12) Uani 1 1 d . A 1 H5 H 0.3113 -0.3003 0.7532 0.111 Uiso 1 1 calc R A 1 C6 C 0.3501(2) -0.0825(7) 0.6810(3) 0.0938(13) Uani 1 1 d . A 1 H6 H 0.3207 -0.1619 0.6346 0.113 Uiso 1 1 calc R A 1 C7 C 0.4049(3) 0.1983(9) 0.6015(2) 0.1169(15) Uani 0.23(2) 1 d P A 1 H7 H 0.3719 0.1178 0.5564 0.14 Uiso 0.23(2) 1 calc PR A 1 C8 C 0.4538(4) 0.3922(10) 0.5954(2) 0.1206(18) Uani 0.77(2) 1 d P A 1 H8 H 0.4479 0.4543 0.5451 0.145 Uiso 0.77(2) 1 calc PR A 1 C9 C 0.5651(3) 0.7093(8) 0.6507(3) 0.1053(15) Uani 1 1 d . A 1 H9 H 0.5556 0.7708 0.5999 0.126 Uiso 1 1 calc R A 1 C10 C 0.6269(3) 0.8127(7) 0.7128(3) 0.1045(14) Uani 1 1 d . A 1 H10 H 0.6535 0.9542 0.7058 0.125 Uiso 1 1 calc R A 1 C11 C 0.7307(3) 0.7917(7) 0.8513(3) 0.0989(14) Uani 1 1 d . A 1 H11 H 0.7598 0.9311 0.8456 0.119 Uiso 1 1 calc R A 1 C12 C 0.7638(3) 0.6716(8) 0.9189(3) 0.1029(14) Uani 1 1 d . A 1 H12 H 0.8152 0.7281 0.9595 0.123 Uiso 1 1 calc R A 1 C13 C 0.7211(2) 0.4645(6) 0.9276(2) 0.0795(10) Uani 1 1 d . A 1 H13 H 0.7467 0.3785 0.9732 0.095 Uiso 1 1 calc R A 1 C14 C 0.64242(18) 0.3835(5) 0.87090(16) 0.0615(9) Uani 0.77(2) 1 d P A 1 H14 H 0.6143 0.2445 0.8788 0.074 Uiso 0.77(2) 1 calc PR A 1 C15 C 0.42809(17) 0.1741(5) 0.81863(17) 0.0554(7) Uani 1 1 d . A 1 C16 C 0.37498(19) -0.0316(5) 0.8210(2) 0.0675(8) Uani 1 1 d . A 1 C17 C 0.45502(19) 0.2382(5) 0.74614(17) 0.0604(8) Uani 1 1 d . A 1 C18 C 0.4054(2) 0.1230(7) 0.6764(2) 0.0825(10) Uani 1 1 d . A 1 C19 C 0.5228(2) 0.4183(5) 0.73855(17) 0.0620(8) Uani 1 1 d . A 1 C20 C 0.5130(3) 0.5038(7) 0.6616(2) 0.0831(10) Uani 1 1 d . A 1 C21 C 0.6036(2) 0.5049(5) 0.80167(18) 0.0602(7) Uani 1 1 d . A 1 C22 C 0.6520(3) 0.7089(5) 0.7887(2) 0.0780(10) Uani 1 1 d . A 1 N1 N 0.44619(15) 0.3189(4) 0.88177(14) 0.0594(8) Uani 0.77(2) 1 d P A 2 N7 N 0.4049(3) 0.1983(9) 0.6015(2) 0.1169(15) Uani 0.77(2) 1 d P A 2 N8 N 0.4538(4) 0.3922(10) 0.5954(2) 0.1206(18) Uani 0.23(2) 1 d P A 2 N14 N 0.64242(18) 0.3835(5) 0.87090(16) 0.0615(9) Uani 0.23(2) 1 d P A 2 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 C1 0.0466(13) 0.0624(16) 0.0739(17) -0.0003(14) 0.0237(12) -0.0026(12) C2 0.0559(17) 0.083(2) 0.0750(19) 0.0057(17) 0.0251(15) -0.0018(16) C3 0.064(2) 0.082(2) 0.109(3) 0.025(2) 0.0413(19) -0.0006(18) C4 0.0532(18) 0.061(2) 0.138(3) 0.021(2) 0.036(2) -0.0002(15) C5 0.0496(19) 0.073(2) 0.150(4) -0.023(3) 0.013(2) 0.0014(17) C6 0.0461(18) 0.098(3) 0.123(3) -0.044(3) -0.004(2) 0.0085(19) C7 0.093(3) 0.168(4) 0.080(3) -0.014(3) 0.0032(19) 0.049(3) C8 0.112(3) 0.177(5) 0.069(3) 0.018(3) 0.017(3) 0.069(3) C9 0.101(3) 0.119(4) 0.119(3) 0.059(3) 0.072(3) 0.053(3) C10 0.103(3) 0.078(3) 0.164(4) 0.038(3) 0.092(3) 0.028(2) C11 0.087(3) 0.072(2) 0.166(4) -0.034(3) 0.082(3) -0.028(2) C12 0.075(2) 0.122(4) 0.126(3) -0.054(3) 0.053(2) -0.036(3) C13 0.0568(18) 0.106(3) 0.082(2) -0.020(2) 0.0298(16) -0.0206(19) C14 0.0489(15) 0.0697(19) 0.0721(19) -0.0035(15) 0.0267(14) -0.0083(14) C15 0.0374(13) 0.0524(16) 0.0747(19) -0.0004(15) 0.0113(13) 0.0060(12) C16 0.0374(14) 0.0532(18) 0.107(2) -0.0082(18) 0.0090(15) 0.0030(13) C17 0.0444(14) 0.0648(18) 0.0684(19) -0.0045(15) 0.0079(13) 0.0153(14) C18 0.0572(19) 0.108(3) 0.075(2) -0.014(2) 0.0020(17) 0.029(2) C19 0.0574(17) 0.0660(18) 0.0698(19) 0.0117(15) 0.0296(15) 0.0218(15) C20 0.078(2) 0.100(3) 0.081(2) 0.025(2) 0.0381(19) 0.040(2) C21 0.0572(16) 0.0541(16) 0.081(2) -0.0004(16) 0.0389(16) 0.0048(14) C22 0.079(2) 0.062(2) 0.117(3) 0.008(2) 0.068(2) 0.0073(18) N1 0.0466(13) 0.0624(16) 0.0739(17) -0.0003(14) 0.0237(12) -0.0026(12) N7 0.093(3) 0.168(4) 0.080(3) -0.014(3) 0.0032(19) 0.049(3) N8 0.112(3) 0.177(5) 0.069(3) 0.018(3) 0.017(3) 0.069(3) N14 0.0489(15) 0.0697(19) 0.0721(19) -0.0035(15) 0.0267(14) -0.0083(14) #----------------------------------------------------------------------------# # 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 C1 C2 1.334(3) . ? C1 C15 1.359(3) . ? C2 C3 1.379(4) . ? C3 C4 1.338(5) . ? C4 C16 1.393(5) . ? C5 C6 1.328(5) . ? C5 C16 1.407(5) . ? C6 C18 1.444(5) . ? C7 C8 1.344(6) . ? C7 C18 1.371(5) . ? C8 C20 1.396(6) . ? C9 C10 1.342(6) . ? C9 C20 1.445(6) . ? C10 C22 1.411(5) . ? C11 C12 1.345(5) . ? C11 C22 1.419(5) . ? C12 C13 1.378(5) . ? C13 C14 1.360(4) . ? C14 C21 1.383(4) . ? C15 C16 1.422(4) . ? C15 C17 1.451(4) . ? C17 C18 1.405(4) . ? C17 C19 1.446(4) . ? C19 C20 1.400(4) . ? C19 C21 1.449(4) . ? C21 C22 1.420(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C15 118.6(3) . . ? C1 C2 C3 123.8(3) . . ? C4 C3 C2 118.3(3) . . ? C3 C4 C16 121.0(3) . . ? C6 C5 C16 121.3(4) . . ? C5 C6 C18 120.7(4) . . ? C8 C7 C18 117.9(4) . . ? C7 C8 C20 122.5(4) . . ? C10 C9 C20 120.9(4) . . ? C9 C10 C22 120.7(4) . . ? C12 C11 C22 121.0(3) . . ? C11 C12 C13 119.8(4) . . ? C14 C13 C12 121.3(4) . . ? C13 C14 C21 120.9(3) . . ? C1 C15 C16 119.9(3) . . ? C1 C15 C17 120.1(2) . . ? C16 C15 C17 119.7(3) . . ? C4 C16 C5 122.3(3) . . ? C4 C16 C15 118.0(3) . . ? C5 C16 C15 119.4(3) . . ? C18 C17 C19 117.6(3) . . ? C18 C17 C15 116.3(3) . . ? C19 C17 C15 126.0(3) . . ? C7 C18 C17 123.0(4) . . ? C7 C18 C6 116.6(4) . . ? C17 C18 C6 120.4(4) . . ? C20 C19 C17 116.2(3) . . ? C20 C19 C21 117.7(3) . . ? C17 C19 C21 126.0(3) . . ? C8 C20 C19 120.7(4) . . ? C8 C20 C9 119.7(4) . . ? C19 C20 C9 119.6(4) . . ? C14 C21 C22 118.4(3) . . ? C14 C21 C19 122.2(3) . . ? C22 C21 C19 119.0(3) . . ? C10 C22 C11 121.8(4) . . ? C10 C22 C21 119.8(4) . . ? C11 C22 C21 118.2(3) . . ? ##END data_4 _database_code_depnum_ccdc_archive 'CCDC 686820' _audit_creation_date 2007-12-30T18:36:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H12 N2' _chemical_formula_weight 280.32 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 9.957(3) _cell_length_b 22.606(6) _cell_length_c 6.2052(16) _cell_angle_alpha 90 _cell_angle_beta 104.210(10) _cell_angle_gamma 90 _cell_volume 1354.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_max 23.25 _cell_measurement_theta_min 3.1 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.1487 _diffrn_reflns_av_unetI/netI 0.1016 _diffrn_reflns_number 10773 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 23.25 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1942 _reflns_number_gt 930 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0768P)^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_number_reflns 1942 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1428 _refine_ls_R_factor_gt 0.063 _refine_ls_wR_factor_ref 0.1845 _refine_ls_wR_factor_gt 0.143 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.262 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # 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 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' N N 0.0061 0.0033 '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 C2 C 0.1074(5) -0.4839(2) 0.2912(9) 0.0688(15) Uani 1 1 d . A 1 H2 H 0.0351 -0.4651 0.1912 0.083 Uiso 1 1 calc R A 1 C3 C 0.1483(6) -0.4621(2) 0.5097(9) 0.0733(15) Uani 0.87 1 d P A 1 H3 H 0.0998 -0.4314 0.5559 0.088 Uiso 0.87 1 calc PR A 1 C4 C 0.2571(6) -0.4861(2) 0.6484(9) 0.0746(16) Uani 1 1 d . A 1 H4 H 0.2861 -0.4717 0.7928 0.09 Uiso 1 1 calc R A 1 C5 C 0.4577(6) -0.5534(3) 0.7068(9) 0.0714(16) Uani 1 1 d . A 1 H5 H 0.4908 -0.5397 0.8515 0.086 Uiso 1 1 calc R A 1 C6 C 0.5336(5) -0.5924(2) 0.6223(9) 0.0703(16) Uani 1 1 d . A 1 H6 H 0.6221 -0.6027 0.7031 0.084 Uiso 1 1 calc R A 1 C7 C 0.5649(5) -0.6552(2) 0.3134(10) 0.0713(16) Uani 1 1 d . A 1 H7 H 0.6545 -0.6641 0.3935 0.086 Uiso 1 1 calc R A 1 C8 C 0.5163(6) -0.6772(2) 0.1073(10) 0.0693(15) Uani 1 1 d . A 1 H8 H 0.5766 -0.6974 0.0402 0.083 Uiso 1 1 calc R A 1 C9 C 0.3259(6) -0.6971(2) -0.2198(9) 0.0708(15) Uani 1 1 d . A 1 H9 H 0.3889 -0.7148 -0.2884 0.085 Uiso 1 1 calc R A 1 C10 C 0.1934(6) -0.6982(2) -0.3250(8) 0.0656(15) Uani 1 1 d . A 1 H10 H 0.1655 -0.7123 -0.4699 0.079 Uiso 1 1 calc R A 1 C11 C -0.0469(7) -0.6878(2) -0.2935(9) 0.0707(16) Uani 1 1 d . A 1 H11 H -0.0748 -0.7036 -0.436 0.085 Uiso 1 1 calc R A 1 C13 C -0.0973(5) -0.6541(2) 0.0191(8) 0.0620(14) Uani 1 1 d . A 1 H13 H -0.1615 -0.6472 0.1027 0.074 Uiso 1 1 calc R A 1 C14 C 0.0366(5) -0.63982(17) 0.1129(7) 0.0535(12) Uani 0.87 1 d P A 1 H14 H 0.0607 -0.6238 0.2553 0.064 Uiso 0.87 1 calc PR A 1 C15 C 0.2758(5) -0.5557(2) 0.3628(7) 0.0489(12) Uani 1 1 d . A 1 C16 C 0.3295(5) -0.5332(2) 0.5795(8) 0.0560(13) Uani 1 1 d . A 1 C17 C 0.3446(4) -0.60563(19) 0.2868(7) 0.0471(12) Uani 1 1 d . A 1 C18 C 0.4781(5) -0.6178(2) 0.4094(8) 0.0550(13) Uani 1 1 d . A 1 C19 C 0.2835(5) -0.63935(18) 0.0885(7) 0.0476(12) Uani 1 1 d . A 1 C20 C 0.3780(5) -0.67059(19) -0.0084(8) 0.0568(13) Uani 1 1 d . A 1 C21 C 0.1394(5) -0.64908(17) -0.0042(7) 0.0501(12) Uani 1 1 d . A 1 C22 C 0.0934(5) -0.67708(18) -0.2117(8) 0.0547(13) Uani 1 1 d . A 1 C1 C 0.1676(4) -0.53041(17) 0.2205(6) 0.0550(11) Uani 0.13 1 d P A 1 H1 H 0.1353 -0.5448 0.0767 0.066 Uiso 0.13 1 calc PR A 1 C12 C -0.1455(5) -0.67767(18) -0.1869(8) 0.0741(14) Uani 0.13 1 d P A 1 H12 H -0.2386 -0.6859 -0.2477 0.089 Uiso 0.13 1 calc PR A 1 N1 N 0.1676(4) -0.53041(17) 0.2205(6) 0.0550(11) Uani 0.87 1 d P B 2 N12 N -0.1455(5) -0.67767(18) -0.1869(8) 0.0741(14) Uani 0.87 1 d P C 2 N3 N 0.1483(6) -0.4621(2) 0.5097(9) 0.0733(15) Uani 0.13 1 d P D 2 N14 N 0.0366(5) -0.63982(17) 0.1129(7) 0.0535(12) Uani 0.13 1 d P E 2 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 C2 0.079(4) 0.054(3) 0.072(4) 0.008(3) 0.014(3) -0.003(3) C3 0.096(4) 0.059(3) 0.070(4) -0.008(3) 0.030(3) -0.012(3) C4 0.102(5) 0.067(4) 0.057(4) -0.010(3) 0.023(3) -0.019(3) C5 0.080(4) 0.078(4) 0.051(3) -0.006(3) 0.007(3) -0.024(3) C6 0.064(3) 0.072(4) 0.065(4) 0.019(3) -0.004(3) -0.019(3) C7 0.059(3) 0.068(4) 0.088(4) 0.019(3) 0.020(3) -0.003(3) C8 0.072(4) 0.060(3) 0.086(4) 0.005(3) 0.039(3) -0.002(3) C9 0.107(5) 0.039(3) 0.077(4) -0.001(3) 0.042(4) -0.002(3) C10 0.116(5) 0.041(3) 0.040(3) -0.004(2) 0.020(3) -0.003(3) C11 0.108(5) 0.044(3) 0.048(3) 0.000(3) -0.005(3) -0.002(3) C13 0.065(3) 0.053(3) 0.066(4) 0.008(3) 0.011(3) 0.003(3) C14 0.068(3) 0.037(3) 0.052(3) 0.006(2) 0.010(3) -0.001(2) C15 0.056(3) 0.050(3) 0.040(3) -0.002(2) 0.011(2) -0.014(2) C16 0.067(3) 0.050(3) 0.052(3) -0.002(3) 0.016(3) -0.014(3) C17 0.058(3) 0.040(3) 0.046(3) 0.006(2) 0.018(2) -0.007(2) C18 0.056(3) 0.055(3) 0.055(3) 0.010(3) 0.014(3) -0.008(3) C19 0.066(3) 0.037(3) 0.042(3) 0.013(2) 0.019(2) -0.005(2) C20 0.073(4) 0.043(3) 0.062(4) 0.004(3) 0.033(3) -0.007(3) C21 0.070(3) 0.033(3) 0.045(3) 0.002(2) 0.010(3) 0.000(2) C22 0.078(4) 0.034(3) 0.047(3) 0.001(2) 0.006(3) -0.001(2) C1 0.066(3) 0.045(3) 0.054(3) 0.001(2) 0.015(2) 0.000(2) C12 0.085(4) 0.057(3) 0.068(3) -0.003(2) -0.004(3) -0.005(2) N1 0.066(3) 0.045(3) 0.054(3) 0.001(2) 0.015(2) 0.000(2) N12 0.085(4) 0.057(3) 0.068(3) -0.003(2) -0.004(3) -0.005(2) N3 0.096(4) 0.059(3) 0.070(4) -0.008(3) 0.030(3) -0.012(3) N14 0.068(3) 0.037(3) 0.052(3) 0.006(2) 0.010(3) -0.001(2) #----------------------------------------------------------------------------# # 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 C2 C1 1.337(6) . ? C2 C3 1.406(6) . ? C3 C4 1.322(6) . ? C4 C16 1.411(6) . ? C5 C6 1.349(7) . ? C5 C16 1.402(6) . ? C6 C18 1.421(6) . ? C7 C8 1.347(6) . ? C7 C18 1.439(6) . ? C8 C20 1.397(6) . ? C9 C10 1.321(6) . ? C9 C20 1.419(6) . ? C10 C22 1.434(6) . ? C11 C12 1.331(6) . ? C11 C22 1.386(6) . ? C13 C14 1.356(6) . ? C13 C12 1.359(5) . ? C14 C21 1.408(6) . ? C15 C1 1.342(5) . ? C15 C16 1.414(6) . ? C15 C17 1.457(6) . ? C17 C18 1.388(5) . ? C17 C19 1.448(5) . ? C19 C20 1.422(6) . ? C19 C21 1.426(6) . ? C21 C22 1.407(6) . ? 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 C2 C3 123.1(5) . . ? C4 C3 C2 118.8(5) . . ? C3 C4 C16 120.7(5) . . ? C6 C5 C16 120.9(5) . . ? C5 C6 C18 119.9(5) . . ? C8 C7 C18 119.9(5) . . ? C7 C8 C20 121.8(5) . . ? C10 C9 C20 123.9(5) . . ? C9 C10 C22 118.8(5) . . ? C12 C11 C22 126.0(5) . . ? C14 C13 C12 125.5(5) . . ? C13 C14 C21 120.4(5) . . ? C1 C15 C16 121.8(4) . . ? C1 C15 C17 118.8(4) . . ? C16 C15 C17 119.2(4) . . ? C5 C16 C4 122.5(5) . . ? C5 C16 C15 119.9(5) . . ? C4 C16 C15 117.2(5) . . ? C18 C17 C19 120.5(4) . . ? C18 C17 C15 116.0(4) . . ? C19 C17 C15 123.4(4) . . ? C17 C18 C6 122.1(5) . . ? C17 C18 C7 118.8(5) . . ? C6 C18 C7 119.0(5) . . ? C20 C19 C21 117.2(4) . . ? C20 C19 C17 115.9(4) . . ? C21 C19 C17 126.5(4) . . ? C8 C20 C9 121.3(5) . . ? C8 C20 C19 120.5(5) . . ? C9 C20 C19 118.1(5) . . ? C22 C21 C14 115.1(5) . . ? C22 C21 C19 120.5(5) . . ? C14 C21 C19 123.8(4) . . ? C11 C22 C21 119.1(5) . . ? C11 C22 C10 121.4(5) . . ? C21 C22 C10 119.3(5) . . ? C2 C1 C15 118.1(4) . . ? C11 C12 C13 113.7(5) . . ? ##END