Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ;Nucleophilic activity of a linked bis{guanidine} leading to formation of a dicationic C4N4-heterocycle ; _publ_requested_category FO _publ_contact_author_name 'Martyn Coles' _publ_contact_author_email M.P.COLES@SUSSEX.AC.UK loop_ _publ_author_name G.Estiu P.B.Hitchcock S.F.Lee S.H.Oakley #===END data_(2a)-sep604 _database_code_depnum_ccdc_archive 'CCDC 617399' _audit_creation_date 2004-09-08T11:29:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H26 D2 N6, 2(C D2 Cl2), 2(Cl)' _chemical_formula_sum 'C18 H26 Cl6 D6 N6' _chemical_formula_weight 551.2 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.3557(5) _cell_length_b 10.5375(3) _cell_length_c 13.1670(3) _cell_angle_alpha 90 _cell_angle_beta 103.550(1) _cell_angle_gamma 90 _cell_volume 2475.91(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10185 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.48 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.25416E-2 _diffrn_orient_matrix_ub_12 -0.306004E-1 _diffrn_orient_matrix_ub_13 0.726384E-1 _diffrn_orient_matrix_ub_21 0.554529E-1 _diffrn_orient_matrix_ub_22 0.136866E-1 _diffrn_orient_matrix_ub_23 0.182428E-1 _diffrn_orient_matrix_ub_31 -0.76726E-2 _diffrn_orient_matrix_ub_32 0.887815E-1 _diffrn_orient_matrix_ub_33 0.22224E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_unetI/netI 0.0215 _diffrn_reflns_number 14266 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 2171 _reflns_number_gt 1994 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The H atoms of the CH2Cl2 solvate molecule were in riding mode; other H atoms were refined. 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^)+(0.0671P)^2^+5.1409P] 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 2171 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.115 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.915 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 0.26598(11) 0.09324(16) 0.52439(13) 0.0225(4) Uani 1 1 d . . . N2 N 0.32127(10) 0.27556(17) 0.60538(13) 0.0225(4) Uani 1 1 d . . . N3 N 0.35902(10) 0.07781(17) 0.67808(13) 0.0236(4) Uani 1 1 d . . . C1 C 0.31549(12) 0.1470(2) 0.60414(16) 0.0208(5) Uani 1 1 d . . . C2 C 0.24822(14) -0.0422(2) 0.53412(18) 0.0282(5) Uani 1 1 d . . . H2B H 0.2164(16) -0.048(3) 0.585(2) 0.035(7) Uiso 1 1 d . . . H2A H 0.2199(14) -0.069(2) 0.463(2) 0.026(6) Uiso 1 1 d . . . C3 C 0.32095(17) -0.1132(2) 0.5682(2) 0.0332(6) Uani 1 1 d . . . H3B H 0.3477(16) -0.103(3) 0.517(2) 0.036(7) Uiso 1 1 d . . . H3A H 0.3129(17) -0.196(3) 0.577(2) 0.040(8) Uiso 1 1 d . . . C4 C 0.36313(16) -0.0617(2) 0.6724(2) 0.0324(6) Uani 1 1 d . . . H4B H 0.4141(18) -0.085(3) 0.689(2) 0.041(8) Uiso 1 1 d . . . H4A H 0.3466(16) -0.092(3) 0.721(2) 0.034(8) Uiso 1 1 d . . . C5 C 0.39465(15) 0.1292(2) 0.78218(18) 0.0303(5) Uani 1 1 d . . . H5B H 0.3720(16) 0.083(3) 0.831(2) 0.038(7) Uiso 1 1 d . . . H5A H 0.4491(17) 0.109(3) 0.796(2) 0.037(7) Uiso 1 1 d . . . C6 C 0.38362(15) 0.2710(2) 0.78906(18) 0.0310(5) Uani 1 1 d . . . H6B H 0.4263(17) 0.305(3) 0.847(2) 0.041(8) Uiso 1 1 d . . . H6A H 0.3388(15) 0.285(2) 0.8057(19) 0.022(6) Uiso 1 1 d . . . C7 C 0.38350(14) 0.3302(2) 0.68464(18) 0.0281(5) Uani 1 1 d . . . H7B H 0.3757(13) 0.419(3) 0.6833(19) 0.024(6) Uiso 1 1 d . . . H7A H 0.4284(17) 0.312(3) 0.667(2) 0.034(7) Uiso 1 1 d . . . C8 C 0.25033(13) 0.3477(2) 0.57868(16) 0.0209(5) Uani 1 1 d . . . H8B H 0.2556(13) 0.415(2) 0.6302(18) 0.017(5) Uiso 1 1 d . . . H8A H 0.2091(13) 0.291(2) 0.5817(17) 0.013(5) Uiso 1 1 d . . . Cl3 Cl 0.20120(3) 0.12586(5) 0.75874(4) 0.0316(2) Uani 1 1 d . . . C1S C 0.04367(18) 0.1825(3) 0.5722(3) 0.0560(8) Uani 1 1 d . . . H1S1 H 0.055 0.1296 0.5157 0.067 Uiso 1 1 calc R . . H1S2 H 0.0853 0.1724 0.6348 0.067 Uiso 1 1 calc R . . Cl1S Cl 0.03734(4) 0.34369(7) 0.53290(6) 0.0479(2) Uani 1 1 d . . . Cl2S Cl -0.03932(6) 0.13009(10) 0.60050(11) 0.0841(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0318(10) 0.0158(9) 0.0175(9) 0.0013(7) 0.0007(7) -0.0019(7) N2 0.0258(10) 0.0186(9) 0.0197(9) -0.0009(7) -0.0014(8) -0.0013(7) N3 0.0288(10) 0.0223(9) 0.0178(9) 0.0014(7) 0.0019(7) 0.0032(8) C1 0.0244(11) 0.0216(11) 0.0167(11) 0.0005(8) 0.0058(9) -0.0002(8) C2 0.0420(14) 0.0165(10) 0.0237(12) 0.0014(9) 0.0026(10) -0.0056(9) C3 0.0526(16) 0.0178(12) 0.0278(13) 0.0015(10) 0.0063(12) 0.0033(11) C4 0.0434(15) 0.0226(12) 0.0281(13) 0.0051(10) 0.0020(11) 0.0060(11) C5 0.0348(14) 0.0341(13) 0.0178(11) 0.0003(10) -0.0022(10) 0.0030(10) C6 0.0308(13) 0.0354(13) 0.0221(12) -0.0064(10) -0.0033(10) 0.0024(10) C7 0.0261(13) 0.0266(13) 0.0272(12) -0.0032(10) -0.0025(10) -0.0035(9) C8 0.0268(12) 0.0191(10) 0.0161(10) -0.0004(8) 0.0033(9) 0.0018(9) Cl3 0.0377(4) 0.0304(3) 0.0266(3) 0.0059(2) 0.0074(2) 0.0028(2) C1S 0.0441(17) 0.0547(19) 0.064(2) 0.0172(16) 0.0013(15) 0.0007(14) Cl1S 0.0472(4) 0.0441(4) 0.0491(5) 0.0028(3) 0.0043(3) -0.0051(3) Cl2S 0.0578(6) 0.0762(7) 0.1196(10) 0.0333(6) 0.0235(6) -0.0104(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 N1 C1 1.343(3) . ? N1 C8 1.459(3) 7_556 ? N1 C2 1.476(3) . ? N2 C1 1.358(3) . ? N2 C7 1.472(3) . ? N2 C8 1.477(3) . ? N3 C1 1.324(3) . ? N3 C4 1.475(3) . ? N3 C5 1.477(3) . ? C2 C3 1.504(4) . ? C3 C4 1.509(4) . ? C5 C6 1.513(3) . ? C6 C7 1.509(3) . ? C8 N1 1.459(3) 7_556 ? C1S Cl2S 1.741(3) . ? C1S Cl1S 1.772(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C8 120.08(18) . 7_556 ? C1 N1 C2 117.59(18) . . ? C8 N1 C2 119.46(17) 7_556 . ? C1 N2 C7 116.38(18) . . ? C1 N2 C8 116.63(18) . . ? C7 N2 C8 117.49(18) . . ? C1 N3 C4 122.76(19) . . ? C1 N3 C5 122.68(19) . . ? C4 N3 C5 113.33(18) . . ? N3 C1 N1 121.57(19) . . ? N3 C1 N2 120.6(2) . . ? N1 C1 N2 117.85(19) . . ? N1 C2 C3 107.9(2) . . ? C2 C3 C4 108.9(2) . . ? N3 C4 C3 112.51(19) . . ? N3 C5 C6 112.43(19) . . ? C7 C6 C5 109.0(2) . . ? N2 C7 C6 108.6(2) . . ? N1 C8 N2 114.72(18) 7_556 . ? Cl2S C1S Cl1S 111.47(19) . . ? #===END data_(2b)-oct1605 _database_code_depnum_ccdc_archive 'CCDC 617400' _audit_creation_date 2005-10-31T15:48:14-00:00 _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_moiety 'C16 H28 N6, 2(C24 H20 B)' _chemical_formula_sum 'C64 H68 B2 N6' _chemical_formula_weight 942.86 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.1882(2) _cell_length_b 14.3840(3) _cell_length_c 16.3407(3) _cell_angle_alpha 90 _cell_angle_beta 104.766(1) _cell_angle_gamma 90 _cell_volume 2542.88(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19017 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.730676E-1 _diffrn_orient_matrix_ub_12 -0.151069E-1 _diffrn_orient_matrix_ub_13 -0.477934E-1 _diffrn_orient_matrix_ub_21 0.424561E-1 _diffrn_orient_matrix_ub_22 -0.576189E-1 _diffrn_orient_matrix_ub_23 -0.121484E-1 _diffrn_orient_matrix_ub_31 -0.374481E-1 _diffrn_orient_matrix_ub_32 -0.358484E-1 _diffrn_orient_matrix_ub_33 0.396667E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0803 _diffrn_reflns_av_unetI/netI 0.0412 _diffrn_reflns_number 35826 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 26.09 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 4993 _reflns_number_gt 4119 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; There is disorder in the cation. 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^)+(0.0729P)^2^+1.5891P] 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 4993 _refine_ls_number_parameters 330 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1547 _refine_ls_wR_factor_gt 0.1451 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.604 _refine_diff_density_min -0.273 _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' B B 0.0013 0.0007 '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 N1 N 0.13588(14) 0.45254(11) 0.05555(10) 0.0308(4) Uani 1 1 d . . . N2 N 0.05774(13) 0.60235(10) 0.04348(9) 0.0261(3) Uani 1 1 d . . . N3 N 0.25601(14) 0.57346(11) 0.12833(10) 0.0325(4) Uani 1 1 d . . . C1 C 0.15154(16) 0.54364(13) 0.07700(11) 0.0254(4) Uani 1 1 d . A . C5 C 0.27704(19) 0.67105(14) 0.15532(14) 0.0395(5) Uani 1 1 d . A . H5A H 0.3353 0.6998 0.1262 0.047 Uiso 1 1 calc R . . H5B H 0.3156 0.6731 0.217 0.047 Uiso 1 1 calc R . . C6 C 0.1591(2) 0.72646(15) 0.13604(13) 0.0407(5) Uani 1 1 d . . . H6A H 0.1127 0.7125 0.1787 0.049 Uiso 1 1 calc R A . H6B H 0.1789 0.7937 0.1393 0.049 Uiso 1 1 calc R . . C7 C 0.08059(18) 0.70343(13) 0.04917(12) 0.0309(4) Uani 1 1 d . A . H7A H 0.0011 0.7373 0.0386 0.037 Uiso 1 1 calc R . . H7B H 0.1234 0.7228 0.0059 0.037 Uiso 1 1 calc R . . C8 C 0.06937(16) 0.43078(13) -0.03148(11) 0.0283(4) Uani 1 1 d . . . H8A H 0.1166 0.3828 -0.0533 0.034 Uiso 1 1 calc R . . H8B H 0.0676 0.4873 -0.0663 0.034 Uiso 1 1 calc R . . B B -0.21748(18) 0.57486(14) 0.23823(12) 0.0241(4) Uani 1 1 d . . . C9 C -0.23790(16) 0.67103(12) 0.18143(11) 0.0256(4) Uani 1 1 d . . . C10 C -0.14641(17) 0.73785(13) 0.18462(12) 0.0300(4) Uani 1 1 d . . . H10 H -0.0686 0.7295 0.2241 0.036 Uiso 1 1 calc R . . C11 C -0.16335(19) 0.81642(13) 0.13272(13) 0.0360(5) Uani 1 1 d . . . H11 H -0.0976 0.8595 0.1374 0.043 Uiso 1 1 calc R . . C12 C -0.2742(2) 0.83188(14) 0.07512(13) 0.0405(5) Uani 1 1 d . . . H12 H -0.2843 0.8832 0.0373 0.049 Uiso 1 1 calc R . . C13 C -0.3713(2) 0.77132(16) 0.07300(14) 0.0475(6) Uani 1 1 d . . . H13 H -0.45 0.7826 0.0355 0.057 Uiso 1 1 calc R . . C14 C -0.3534(2) 0.69420(15) 0.12567(13) 0.0403(5) Uani 1 1 d . . . H14 H -0.4221 0.6549 0.1243 0.048 Uiso 1 1 calc R . . C15 C -0.32508(16) 0.56705(14) 0.29079(11) 0.0287(4) Uani 1 1 d . . . C16 C -0.38619(18) 0.64453(17) 0.31213(13) 0.0407(5) Uani 1 1 d . . . H16 H -0.3677 0.7043 0.2938 0.049 Uiso 1 1 calc R . . C17 C -0.4735(2) 0.6371(3) 0.35952(15) 0.0609(8) Uani 1 1 d . . . H17 H -0.514 0.6913 0.372 0.073 Uiso 1 1 calc R . . C18 C -0.5011(2) 0.5522(3) 0.38815(14) 0.0667(9) Uani 1 1 d . . . H18 H -0.5598 0.5472 0.4209 0.08 Uiso 1 1 calc R . . C19 C -0.4424(2) 0.4745(2) 0.36876(15) 0.0625(8) Uani 1 1 d . . . H19 H -0.4604 0.4153 0.3885 0.075 Uiso 1 1 calc R . . C20 C -0.35657(19) 0.48158(17) 0.32046(13) 0.0429(5) Uani 1 1 d . . . H20 H -0.3182 0.4266 0.3072 0.051 Uiso 1 1 calc R . . C21 C -0.23300(16) 0.48111(13) 0.17694(11) 0.0258(4) Uani 1 1 d . . . C22 C -0.15901(19) 0.40257(13) 0.19715(12) 0.0352(5) Uani 1 1 d . . . H22 H -0.0882 0.406 0.2438 0.042 Uiso 1 1 calc R . . C23 C -0.1830(2) 0.31913(14) 0.15273(13) 0.0387(5) Uani 1 1 d . . . H23 H -0.1288 0.2678 0.1691 0.046 Uiso 1 1 calc R . . C24 C -0.28504(19) 0.31081(14) 0.08516(13) 0.0354(5) Uani 1 1 d . . . H24 H -0.3053 0.253 0.0569 0.043 Uiso 1 1 calc R . . C25 C -0.3574(2) 0.38881(17) 0.05934(15) 0.0478(6) Uani 1 1 d . . . H25 H -0.4259 0.3855 0.0111 0.057 Uiso 1 1 calc R . . C26 C -0.33031(19) 0.47189(16) 0.10349(14) 0.0439(5) Uani 1 1 d . . . H26 H -0.3797 0.5248 0.0832 0.053 Uiso 1 1 calc R . . C27 C -0.08075(16) 0.57595(12) 0.30630(11) 0.0240(4) Uani 1 1 d . . . C28 C 0.02830(16) 0.56498(12) 0.27976(12) 0.0272(4) Uani 1 1 d . . . H28 H 0.0218 0.5573 0.2211 0.033 Uiso 1 1 calc R . . C29 C 0.14550(17) 0.56485(13) 0.33548(13) 0.0315(4) Uani 1 1 d . . . H29 H 0.2168 0.5578 0.3146 0.038 Uiso 1 1 calc R . . C30 C 0.15761(18) 0.57517(12) 0.42177(13) 0.0323(4) Uani 1 1 d . . . H30 H 0.2369 0.5741 0.4605 0.039 Uiso 1 1 calc R . . C31 C 0.05302(18) 0.58690(13) 0.45015(12) 0.0328(4) Uani 1 1 d . . . H31 H 0.0602 0.5945 0.509 0.039 Uiso 1 1 calc R . . C32 C -0.06375(17) 0.58774(13) 0.39336(11) 0.0296(4) Uani 1 1 d . . . H32 H -0.1343 0.5967 0.4147 0.036 Uiso 1 1 calc R . . C2 C 0.2158(2) 0.37918(16) 0.10342(15) 0.0477(6) Uani 0.822(7) 1 d P A 1 H2A H 0.2591 0.3472 0.0656 0.057 Uiso 0.822(7) 1 calc PR A 1 H2B H 0.164 0.3327 0.123 0.057 Uiso 0.822(7) 1 calc PR A 1 C3 C 0.3095(3) 0.41761(19) 0.17834(19) 0.0476(10) Uani 0.822(7) 1 d P A 1 H3A H 0.378 0.3726 0.1971 0.057 Uiso 0.822(7) 1 calc PR A 1 H3B H 0.2706 0.4274 0.2257 0.057 Uiso 0.822(7) 1 calc PR A 1 C4 C 0.3595(2) 0.50846(16) 0.15540(15) 0.0451(5) Uani 0.822(7) 1 d P A 1 H4A H 0.4211 0.5339 0.2049 0.054 Uiso 0.822(7) 1 calc PR A 1 H4B H 0.4005 0.4988 0.1091 0.054 Uiso 0.822(7) 1 calc PR A 1 C2A C 0.2158(2) 0.37918(16) 0.10342(15) 0.0477(6) Uani 0.178(7) 1 d P A 2 H2A1 H 0.1941 0.3664 0.1574 0.057 Uiso 0.178(7) 1 calc PR A 2 H2A2 H 0.2073 0.321 0.0701 0.057 Uiso 0.178(7) 1 calc PR A 2 C3A C 0.3418(12) 0.4156(9) 0.1192(9) 0.044(4) Uiso 0.178(7) 1 d P A 2 H3A1 H 0.3982 0.3725 0.1579 0.053 Uiso 0.178(7) 1 calc PR A 2 H3A2 H 0.3661 0.4161 0.065 0.053 Uiso 0.178(7) 1 calc PR A 2 C4A C 0.3595(2) 0.50846(16) 0.15540(15) 0.0451(5) Uani 0.178(7) 1 d P A 2 H4A1 H 0.4329 0.5362 0.1415 0.054 Uiso 0.178(7) 1 calc PR A 2 H4A2 H 0.3786 0.5026 0.2178 0.054 Uiso 0.178(7) 1 calc PR 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 N1 0.0300(8) 0.0264(8) 0.0298(8) -0.0033(6) -0.0036(7) 0.0014(6) N2 0.0254(8) 0.0252(8) 0.0259(8) -0.0029(6) 0.0030(6) -0.0018(6) N3 0.0266(8) 0.0362(9) 0.0303(8) -0.0048(7) -0.0010(7) -0.0026(7) C1 0.0253(9) 0.0305(9) 0.0198(8) -0.0011(7) 0.0048(7) -0.0039(7) C5 0.0380(11) 0.0372(11) 0.0378(11) -0.0077(9) -0.0002(9) -0.0115(9) C6 0.0438(12) 0.0364(11) 0.0408(12) -0.0092(9) 0.0089(10) -0.0102(9) C7 0.0331(10) 0.0247(9) 0.0348(10) -0.0023(8) 0.0088(8) -0.0026(8) C8 0.0262(9) 0.0325(10) 0.0263(9) -0.0062(7) 0.0068(7) -0.0018(7) B 0.0212(10) 0.0267(10) 0.0240(10) -0.0015(8) 0.0047(8) -0.0014(8) C9 0.0273(9) 0.0270(9) 0.0216(8) -0.0034(7) 0.0048(7) -0.0010(7) C10 0.0248(9) 0.0283(10) 0.0349(10) -0.0006(8) 0.0041(8) 0.0015(7) C11 0.0361(11) 0.0257(9) 0.0450(12) 0.0006(8) 0.0083(9) -0.0019(8) C12 0.0507(13) 0.0294(10) 0.0365(11) 0.0056(8) 0.0023(10) -0.0012(9) C13 0.0476(13) 0.0382(12) 0.0433(12) 0.0061(10) -0.0126(10) -0.0036(10) C14 0.0351(11) 0.0358(11) 0.0419(12) 0.0039(9) -0.0052(9) -0.0061(9) C15 0.0199(9) 0.0439(11) 0.0195(8) -0.0008(7) -0.0001(7) -0.0001(8) C16 0.0294(10) 0.0587(14) 0.0322(10) -0.0171(10) 0.0045(8) 0.0014(9) C17 0.0312(12) 0.116(2) 0.0332(12) -0.0300(14) 0.0039(10) 0.0093(14) C18 0.0240(11) 0.151(3) 0.0267(11) 0.0021(15) 0.0090(9) -0.0028(15) C19 0.0328(12) 0.110(2) 0.0437(13) 0.0340(15) 0.0080(11) -0.0080(14) C20 0.0273(10) 0.0614(14) 0.0403(12) 0.0191(10) 0.0092(9) 0.0005(10) C21 0.0221(9) 0.0298(9) 0.0271(9) -0.0004(7) 0.0092(7) -0.0029(7) C22 0.0421(11) 0.0289(10) 0.0277(10) 0.0028(8) -0.0036(8) 0.0002(8) C23 0.0487(13) 0.0271(10) 0.0358(11) 0.0013(8) 0.0022(9) 0.0057(9) C24 0.0375(11) 0.0319(10) 0.0377(11) -0.0094(8) 0.0110(9) -0.0060(8) C25 0.0330(11) 0.0497(13) 0.0517(13) -0.0179(11) -0.0058(10) 0.0038(10) C26 0.0317(11) 0.0426(12) 0.0489(13) -0.0136(10) -0.0050(9) 0.0090(9) C27 0.0237(9) 0.0215(8) 0.0254(9) 0.0018(7) 0.0034(7) -0.0014(7) C28 0.0261(9) 0.0278(9) 0.0268(9) 0.0013(7) 0.0049(7) -0.0003(7) C29 0.0229(9) 0.0292(10) 0.0408(11) 0.0022(8) 0.0054(8) 0.0014(7) C30 0.0269(10) 0.0246(9) 0.0374(11) 0.0031(8) -0.0063(8) -0.0027(7) C31 0.0384(11) 0.0295(10) 0.0258(9) -0.0003(7) -0.0009(8) -0.0056(8) C32 0.0293(10) 0.0314(10) 0.0276(9) -0.0021(7) 0.0063(8) -0.0035(8) C2 0.0422(12) 0.0358(12) 0.0528(14) 0.0058(10) -0.0107(10) 0.0044(10) C3 0.0448(17) 0.0394(15) 0.0443(18) 0.0012(12) -0.0146(13) 0.0063(12) C4 0.0283(11) 0.0495(13) 0.0481(13) -0.0033(10) -0.0074(9) 0.0018(9) C2A 0.0422(12) 0.0358(12) 0.0528(14) 0.0058(10) -0.0107(10) 0.0044(10) C4A 0.0283(11) 0.0495(13) 0.0481(13) -0.0033(10) -0.0074(9) 0.0018(9) #----------------------------------------------------------------------------# # 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 1.356(2) . ? N1 C8 1.461(2) . ? N1 C2 1.473(3) . ? N2 C1 1.350(2) . ? N2 C8 1.465(2) 3_565 ? N2 C7 1.475(2) . ? N3 C1 1.324(2) . ? N3 C4 1.466(3) . ? N3 C5 1.472(2) . ? C5 C6 1.504(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.504(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 N2 1.465(2) 3_565 ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? B C27 1.646(3) . ? B C9 1.649(3) . ? B C15 1.651(3) . ? B C21 1.662(3) . ? C9 C10 1.395(3) . ? C9 C14 1.418(3) . ? C10 C11 1.397(3) . ? C10 H10 0.95 . ? C11 C12 1.371(3) . ? C11 H11 0.95 . ? C12 C13 1.386(3) . ? C12 H12 0.95 . ? C13 C14 1.387(3) . ? C13 H13 0.95 . ? C14 H14 0.95 . ? C15 C16 1.397(3) . ? C15 C20 1.399(3) . ? C16 C17 1.397(3) . ? C16 H16 0.95 . ? C17 C18 1.371(5) . ? C17 H17 0.95 . ? C18 C19 1.374(4) . ? C18 H18 0.95 . ? C19 C20 1.393(3) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 C22 1.390(3) . ? C21 C26 1.406(3) . ? C22 C23 1.393(3) . ? C22 H22 0.95 . ? C23 C24 1.376(3) . ? C23 H23 0.95 . ? C24 C25 1.385(3) . ? C24 H24 0.95 . ? C25 C26 1.389(3) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C27 C32 1.397(2) . ? C27 C28 1.404(3) . ? C28 C29 1.393(3) . ? C28 H28 0.95 . ? C29 C30 1.390(3) . ? C29 H29 0.95 . ? C30 C31 1.375(3) . ? C30 H30 0.95 . ? C31 C32 1.396(3) . ? C31 H31 0.95 . ? C32 H32 0.95 . ? C2 C3 1.499(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.506(4) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C3A H3A1 0.99 . ? C3A H3A2 0.99 . ? 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 C8 117.30(15) . . ? C1 N1 C2 122.29(16) . . ? C8 N1 C2 116.95(16) . . ? C1 N2 C8 118.60(15) . 3_565 ? C1 N2 C7 119.13(15) . . ? C8 N2 C7 118.42(15) 3_565 . ? C1 N3 C4 119.09(17) . . ? C1 N3 C5 123.12(16) . . ? C4 N3 C5 117.65(16) . . ? N3 C1 N2 121.59(16) . . ? N3 C1 N1 120.77(17) . . ? N2 C1 N1 117.63(15) . . ? N3 C5 C6 112.20(16) . . ? N3 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N3 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 110.56(17) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C6 109.07(16) . . ? N2 C7 H7A 109.9 . . ? C6 C7 H7A 109.9 . . ? N2 C7 H7B 109.9 . . ? C6 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N1 C8 N2 115.86(15) . 3_565 ? N1 C8 H8A 108.3 . . ? N2 C8 H8A 108.3 3_565 . ? N1 C8 H8B 108.3 . . ? N2 C8 H8B 108.3 3_565 . ? H8A C8 H8B 107.4 . . ? C27 B C9 110.11(14) . . ? C27 B C15 108.92(14) . . ? C9 B C15 109.58(14) . . ? C27 B C21 110.56(14) . . ? C9 B C21 111.30(14) . . ? C15 B C21 106.27(14) . . ? C10 C9 C14 113.69(17) . . ? C10 C9 B 124.18(16) . . ? C14 C9 B 122.11(16) . . ? C9 C10 C11 123.37(18) . . ? C9 C10 H10 118.3 . . ? C11 C10 H10 118.3 . . ? C12 C11 C10 120.48(19) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 118.78(19) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C12 C13 C14 120.0(2) . . ? C12 C13 H13 120 . . ? C14 C13 H13 120 . . ? C13 C14 C9 123.36(19) . . ? C13 C14 H14 118.3 . . ? C9 C14 H14 118.3 . . ? C16 C15 C20 115.58(19) . . ? C16 C15 B 122.92(18) . . ? C20 C15 B 121.42(17) . . ? C17 C16 C15 122.2(2) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C18 C17 C16 120.5(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 118.9(2) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C18 C19 C20 120.7(3) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C15 122.1(2) . . ? C19 C20 H20 118.9 . . ? C15 C20 H20 118.9 . . ? C22 C21 C26 114.26(17) . . ? C22 C21 B 123.50(16) . . ? C26 C21 B 122.00(16) . . ? C21 C22 C23 123.54(18) . . ? C21 C22 H22 118.2 . . ? C23 C22 H22 118.2 . . ? C24 C23 C22 120.23(19) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 118.35(18) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? C24 C25 C26 120.4(2) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 122.9(2) . . ? C25 C26 H26 118.5 . . ? C21 C26 H26 118.5 . . ? C32 C27 C28 115.14(16) . . ? C32 C27 B 123.45(16) . . ? C28 C27 B 121.41(15) . . ? C29 C28 C27 123.07(17) . . ? C29 C28 H28 118.5 . . ? C27 C28 H28 118.5 . . ? C30 C29 C28 119.69(18) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C31 C30 C29 118.96(17) . . ? C31 C30 H30 120.5 . . ? C29 C30 H30 120.5 . . ? C30 C31 C32 120.63(18) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C31 C32 C27 122.50(18) . . ? C31 C32 H32 118.7 . . ? C27 C32 H32 118.7 . . ? N1 C2 C3 111.89(19) . . ? N1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 110.1(2) . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.2 . . ? N3 C4 C3 108.25(19) . . ? N3 C4 H4A 110 . . ? C3 C4 H4A 110 . . ? N3 C4 H4B 110 . . ? C3 C4 H4B 110 . . ? H4A C4 H4B 108.4 . . ? H3A1 C3A H3A2 107.5 . . ? #===END data_(5b)-jul306 _database_code_depnum_ccdc_archive 'CCDC 617401' _audit_creation_date 2006-07-05T14:06:51-00:00 _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_moiety 'C29 H40 N6, 2(C24 H20 B)' _chemical_formula_sum 'C77 H80 B2 N6' _chemical_formula_weight 1111.09 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 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' _cell_length_a 18.8240(6) _cell_length_b 13.0677(2) _cell_length_c 26.2401(7) _cell_angle_alpha 90 _cell_angle_beta 105.854(1) _cell_angle_gamma 90 _cell_volume 6209.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 17441 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2376 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.448977E-1 _diffrn_orient_matrix_ub_12 -0.27859E-1 _diffrn_orient_matrix_ub_13 -0.85182E-2 _diffrn_orient_matrix_ub_21 0.117994E-1 _diffrn_orient_matrix_ub_22 -0.412814E-1 _diffrn_orient_matrix_ub_23 0.333511E-1 _diffrn_orient_matrix_ub_31 -0.299118E-1 _diffrn_orient_matrix_ub_32 -0.58101E-1 _diffrn_orient_matrix_ub_33 -0.196119E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0939 _diffrn_reflns_av_unetI/netI 0.072 _diffrn_reflns_number 18974 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 26.05 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.971 _reflns_number_total 5963 _reflns_number_gt 4875 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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)' #----------------------------------------------------------------------------# # 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^)+(0.0784P)^2^+2.8750P] 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 5963 _refine_ls_number_parameters 766 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1483 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(3) _refine_diff_density_max 0.359 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # 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' B B 0.0013 0.0007 '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 0.23109(17) 0.2671(2) 0.32074(13) 0.0347(7) Uani 1 1 d . . . N2 N 0.34487(16) 0.3356(2) 0.36825(12) 0.0290(7) Uani 1 1 d . . . N3 N 0.33818(18) 0.1693(2) 0.33990(14) 0.0368(8) Uani 1 1 d . . . N4 N 0.35498(18) 0.4273(2) 0.44972(13) 0.0337(7) Uani 1 1 d . . . N5 N 0.39230(19) 0.5955(2) 0.43780(14) 0.0387(8) Uani 1 1 d . . . N6 N 0.45250(19) 0.5001(3) 0.51220(13) 0.0383(8) Uani 1 1 d . . . C1 C 0.3037(2) 0.2565(3) 0.34179(14) 0.0284(8) Uani 1 1 d . . . C2 C 0.1842(2) 0.1760(3) 0.3058(2) 0.0466(11) Uani 1 1 d . . . H2A H 0.1646 0.1737 0.2668 0.056 Uiso 1 1 calc R . . H2B H 0.1417 0.1815 0.3211 0.056 Uiso 1 1 calc R . . C3 C 0.2253(3) 0.0778(4) 0.3248(2) 0.0574(13) Uani 1 1 d . . . H3A H 0.2334 0.0706 0.3635 0.069 Uiso 1 1 calc R . . H3B H 0.1959 0.0186 0.3072 0.069 Uiso 1 1 calc R . . C4 C 0.2973(2) 0.0803(3) 0.31202(19) 0.0454(11) Uani 1 1 d . . . H4A H 0.3252 0.0164 0.324 0.054 Uiso 1 1 calc R . . H4B H 0.2897 0.0871 0.2733 0.054 Uiso 1 1 calc R . . C5 C 0.4161(2) 0.1621(3) 0.36919(19) 0.0412(10) Uani 1 1 d . . . H5A H 0.4373 0.0972 0.3606 0.049 Uiso 1 1 calc R . . H5B H 0.4215 0.1638 0.4078 0.049 Uiso 1 1 calc R . . C6 C 0.4553(2) 0.2519(3) 0.35325(19) 0.0432(10) Uani 1 1 d . . . H6A H 0.4521 0.2472 0.315 0.052 Uiso 1 1 calc R . . H6B H 0.5081 0.2505 0.3733 0.052 Uiso 1 1 calc R . . C7 C 0.4210(2) 0.3511(3) 0.36412(18) 0.0388(9) Uani 1 1 d . . . H7A H 0.4517 0.3809 0.3976 0.047 Uiso 1 1 calc R . . H7B H 0.4202 0.4002 0.3352 0.047 Uiso 1 1 calc R . . C8 C 0.3128(2) 0.4134(3) 0.39469(16) 0.0347(9) Uani 1 1 d . . . H8A H 0.2616 0.3937 0.3934 0.042 Uiso 1 1 calc R . . H8B H 0.3109 0.4792 0.3756 0.042 Uiso 1 1 calc R . . C9 C 0.3996(2) 0.5077(3) 0.46653(16) 0.0346(9) Uani 1 1 d . . . C10 C 0.3593(2) 0.3391(3) 0.48520(18) 0.0419(10) Uani 1 1 d . . . H10A H 0.3324 0.2802 0.4651 0.05 Uiso 1 1 calc R . . H10B H 0.3361 0.3564 0.5137 0.05 Uiso 1 1 calc R . . C11 C 0.4388(3) 0.3115(3) 0.50879(18) 0.0476(11) Uani 1 1 d . . . H11A H 0.462 0.2934 0.4804 0.057 Uiso 1 1 calc R . . H11B H 0.4426 0.2518 0.5326 0.057 Uiso 1 1 calc R . . C12 C 0.4778(2) 0.4028(3) 0.53963(17) 0.0459(10) Uani 1 1 d . . . H12A H 0.4685 0.404 0.575 0.055 Uiso 1 1 calc R . . H12B H 0.5316 0.3958 0.5449 0.055 Uiso 1 1 calc R . . C13 C 0.4887(3) 0.5908(4) 0.54295(19) 0.0537(12) Uani 1 1 d . . . H13A H 0.4778 0.5916 0.5778 0.064 Uiso 1 1 calc R . . H13B H 0.5429 0.5851 0.5493 0.064 Uiso 1 1 calc R . . C14 C 0.4630(3) 0.6887(4) 0.51480(19) 0.0532(12) Uani 1 1 d . . . H14A H 0.5001 0.7432 0.5277 0.064 Uiso 1 1 calc R . . H14B H 0.4158 0.7104 0.5213 0.064 Uiso 1 1 calc R . . C15 C 0.4524(3) 0.6705(3) 0.45652(19) 0.0482(11) Uani 1 1 d . . . H15A H 0.4397 0.7355 0.4368 0.058 Uiso 1 1 calc R . . H15B H 0.4987 0.6439 0.4504 0.058 Uiso 1 1 calc R . . C16 C 0.1979(2) 0.3623(3) 0.29403(17) 0.0382(9) Uani 1 1 d . . . H16A H 0.2306 0.4207 0.3087 0.046 Uiso 1 1 calc R . . H16B H 0.1498 0.3741 0.3017 0.046 Uiso 1 1 calc R . . C17 C 0.1861(2) 0.3589(3) 0.23535(15) 0.0324(8) Uani 1 1 d . . . C18 C 0.2447(2) 0.3522(4) 0.2130(2) 0.0580(13) Uani 1 1 d . . . H18 H 0.2936 0.3494 0.2358 0.07 Uiso 1 1 calc R . . C19 C 0.2347(3) 0.3496(4) 0.1594(2) 0.0587(13) Uani 1 1 d . . . H19 H 0.276 0.3427 0.1455 0.07 Uiso 1 1 calc R . . C20 C 0.1655(3) 0.3568(4) 0.1260(2) 0.0610(14) Uani 1 1 d . . . H20 H 0.1584 0.362 0.0888 0.073 Uiso 1 1 calc R . . C21 C 0.1064(3) 0.3564(6) 0.1467(2) 0.0787(19) Uani 1 1 d . . . H21 H 0.0577 0.3541 0.1237 0.094 Uiso 1 1 calc R . . C22 C 0.1168(3) 0.3594(5) 0.20110(18) 0.0594(14) Uani 1 1 d . . . H22 H 0.075 0.3619 0.2148 0.071 Uiso 1 1 calc R . . C23 C 0.3194(3) 0.6414(3) 0.41099(17) 0.0427(10) Uani 1 1 d . . . H23A H 0.318 0.7121 0.4241 0.051 Uiso 1 1 calc R . . H23B H 0.2804 0.6019 0.421 0.051 Uiso 1 1 calc R . . C24 C 0.3019(2) 0.6441(3) 0.35088(17) 0.0381(9) Uani 1 1 d . . . C25 C 0.3550(3) 0.6337(4) 0.32388(18) 0.0466(10) Uani 1 1 d . . . H25 H 0.4056 0.6298 0.3433 0.056 Uiso 1 1 calc R . . C26 C 0.3363(3) 0.6290(4) 0.2689(2) 0.0539(12) Uani 1 1 d . . . H26 H 0.3738 0.6216 0.2512 0.065 Uiso 1 1 calc R . . C27 C 0.2627(3) 0.6349(4) 0.2399(2) 0.0533(12) Uani 1 1 d . . . H27 H 0.2493 0.6321 0.2023 0.064 Uiso 1 1 calc R . . C28 C 0.2095(3) 0.6450(4) 0.2666(2) 0.0518(11) Uani 1 1 d . . . H28 H 0.1589 0.6483 0.2473 0.062 Uiso 1 1 calc R . . C29 C 0.2290(3) 0.6503(3) 0.32094(19) 0.0461(11) Uani 1 1 d . . . H29 H 0.1914 0.6585 0.3385 0.055 Uiso 1 1 calc R . . B1 B 0.0368(2) 0.9486(3) 0.20965(18) 0.0343(10) Uani 1 1 d . A 1 B2 B 0.5795(2) 0.9513(3) 0.45154(19) 0.0329(9) Uani 1 1 d . B 1 C30 C -0.0256(2) 1.0355(3) 0.18228(15) 0.0342(8) Uani 1 1 d . A 1 C31 C -0.0118(2) 1.1407(3) 0.18900(17) 0.0383(9) Uani 1 1 d . A 1 H31 H 0.0352 1.1621 0.2103 0.046 Uiso 1 1 calc R A 1 C32 C -0.0633(3) 1.2151(3) 0.16610(18) 0.0454(10) Uani 1 1 d . A 1 H32 H -0.0507 1.2855 0.1712 0.054 Uiso 1 1 calc R A 1 C33 C -0.1330(2) 1.1869(4) 0.13579(18) 0.0460(11) Uani 1 1 d . A 1 H33 H -0.1687 1.2376 0.1205 0.055 Uiso 1 1 calc R A 1 C34 C -0.1498(2) 1.0852(4) 0.12812(17) 0.0428(10) Uani 1 1 d . A 1 H34 H -0.1975 1.0648 0.1077 0.051 Uiso 1 1 calc R A 1 C35 C -0.0969(2) 1.0114(3) 0.15024(17) 0.0396(9) Uani 1 1 d . A 1 H35 H -0.1094 0.9413 0.1434 0.047 Uiso 1 1 calc R A 1 C36 C 0.0047(2) 0.8330(3) 0.19108(15) 0.0321(8) Uani 1 1 d . A 1 C37 C -0.0548(2) 0.7938(3) 0.20756(17) 0.0400(9) Uani 1 1 d . A 1 H37 H -0.0744 0.8339 0.2307 0.048 Uiso 1 1 calc R A 1 C38 C -0.0866(2) 0.6991(3) 0.19159(18) 0.0447(10) Uani 1 1 d . A 1 H38 H -0.1273 0.6761 0.2034 0.054 Uiso 1 1 calc R A 1 C39 C -0.0587(3) 0.6386(3) 0.15851(19) 0.0485(11) Uani 1 1 d . A 1 H39 H -0.0797 0.5735 0.1476 0.058 Uiso 1 1 calc R A 1 C40 C -0.0005(3) 0.6735(3) 0.14154(19) 0.0483(11) Uani 1 1 d . A 1 H40 H 0.0186 0.6322 0.1186 0.058 Uiso 1 1 calc R A 1 C41 C 0.0310(2) 0.7681(3) 0.15740(17) 0.0383(9) Uani 1 1 d . A 1 H41 H 0.0716 0.7899 0.1452 0.046 Uiso 1 1 calc R A 1 C42 C 0.0549(2) 0.9528(3) 0.27522(16) 0.0318(8) Uani 1 1 d . A 1 C43 C 0.0365(2) 1.0339(3) 0.30372(16) 0.0338(8) Uani 1 1 d . A 1 H43 H 0.0074 1.0881 0.2847 0.041 Uiso 1 1 calc R A 1 C44 C 0.0590(2) 1.0387(3) 0.35898(17) 0.0394(9) Uani 1 1 d . A 1 H44 H 0.0457 1.0961 0.3766 0.047 Uiso 1 1 calc R A 1 C45 C 0.1003(2) 0.9609(3) 0.38817(17) 0.0436(10) Uani 1 1 d . A 1 H45 H 0.1172 0.9652 0.4257 0.052 Uiso 1 1 calc R A 1 C46 C 0.1166(2) 0.8760(3) 0.36144(17) 0.0436(10) Uani 1 1 d . A 1 H46 H 0.1435 0.8203 0.3808 0.052 Uiso 1 1 calc R A 1 C47 C 0.0934(2) 0.8726(3) 0.30652(17) 0.0388(9) Uani 1 1 d . A 1 H47 H 0.1042 0.813 0.2892 0.047 Uiso 1 1 calc R A 1 C48 C 0.1154(2) 0.9678(3) 0.19338(16) 0.0349(9) Uani 1 1 d . A 1 C49 C 0.1263(2) 1.0450(3) 0.15967(18) 0.0427(10) Uani 1 1 d . A 1 H49 H 0.0875 1.0925 0.1462 0.051 Uiso 1 1 calc R A 1 C50 C 0.1923(3) 1.0555(4) 0.1448(2) 0.0538(12) Uani 1 1 d . A 1 H50 H 0.197 1.109 0.1214 0.065 Uiso 1 1 calc R A 1 C51 C 0.2499(2) 0.9890(4) 0.1639(2) 0.0556(13) Uani 1 1 d . A 1 H51 H 0.2947 0.9961 0.1543 0.067 Uiso 1 1 calc R A 1 C52 C 0.2410(2) 0.9111(4) 0.1976(2) 0.0505(12) Uani 1 1 d . A 1 H52 H 0.28 0.864 0.2113 0.061 Uiso 1 1 calc R A 1 C53 C 0.1754(2) 0.9024(3) 0.2111(2) 0.0464(11) Uani 1 1 d . A 1 H53 H 0.1709 0.8481 0.2341 0.056 Uiso 1 1 calc R A 1 C54 C 0.5579(2) 0.9493(3) 0.38678(16) 0.0334(8) Uani 1 1 d . B 1 C55 C 0.5676(2) 1.0327(3) 0.35576(16) 0.0350(9) Uani 1 1 d . B 1 H55 H 0.5969 1.0886 0.3728 0.042 Uiso 1 1 calc R B 1 C56 C 0.5362(2) 1.0376(3) 0.30099(17) 0.0425(10) Uani 1 1 d . B 1 H56 H 0.5433 1.0967 0.2819 0.051 Uiso 1 1 calc R B 1 C57 C 0.4948(2) 0.9566(4) 0.27457(19) 0.0459(10) Uani 1 1 d . B 1 H57 H 0.4721 0.9604 0.2375 0.055 Uiso 1 1 calc R B 1 C58 C 0.4871(2) 0.8702(4) 0.30272(18) 0.0477(11) Uani 1 1 d . B 1 H58 H 0.4603 0.8129 0.285 0.057 Uiso 1 1 calc R B 1 C59 C 0.5188(2) 0.8674(3) 0.35745(18) 0.0417(10) Uani 1 1 d . B 1 H59 H 0.5135 0.8066 0.3759 0.05 Uiso 1 1 calc R B 1 C60 C 0.6371(2) 1.0468(3) 0.47554(15) 0.0353(9) Uani 1 1 d . B 1 C61 C 0.6138(3) 1.1488(3) 0.47151(17) 0.0433(10) Uani 1 1 d . B 1 H61 H 0.5632 1.1629 0.4549 0.052 Uiso 1 1 calc R B 1 C62 C 0.6605(3) 1.2307(3) 0.49039(18) 0.0493(12) Uani 1 1 d . B 1 H62 H 0.6421 1.2987 0.486 0.059 Uiso 1 1 calc R B 1 C63 C 0.7346(3) 1.2122(4) 0.5158(2) 0.0533(12) Uani 1 1 d . B 1 H63 H 0.7673 1.2675 0.5288 0.064 Uiso 1 1 calc R B 1 C64 C 0.7594(2) 1.1135(4) 0.52175(18) 0.0458(11) Uani 1 1 d . B 1 H64 H 0.8095 1.0999 0.5398 0.055 Uiso 1 1 calc R B 1 C65 C 0.7123(2) 1.0334(3) 0.50166(17) 0.0392(9) Uani 1 1 d . B 1 H65 H 0.7316 0.9658 0.5057 0.047 Uiso 1 1 calc R B 1 C66 C 0.6205(2) 0.8435(3) 0.47758(17) 0.0342(9) Uani 1 1 d . B 1 C67 C 0.6316(2) 0.8206(3) 0.53154(18) 0.0408(9) Uani 1 1 d . B 1 H67 H 0.6132 0.8667 0.5529 0.049 Uiso 1 1 calc R B 1 C68 C 0.6684(2) 0.7331(4) 0.5548(2) 0.0506(12) Uani 1 1 d . B 1 H68 H 0.674 0.7203 0.5913 0.061 Uiso 1 1 calc R B 1 C69 C 0.6970(2) 0.6647(3) 0.5257(2) 0.0511(12) Uani 1 1 d . B 1 H69 H 0.7224 0.6051 0.5417 0.061 Uiso 1 1 calc R B 1 C70 C 0.6878(3) 0.6850(3) 0.4727(2) 0.0506(12) Uani 1 1 d . B 1 H70 H 0.7066 0.6384 0.4518 0.061 Uiso 1 1 calc R B 1 C71 C 0.6515(2) 0.7726(3) 0.44965(18) 0.0409(10) Uani 1 1 d . B 1 H71 H 0.6475 0.7853 0.4133 0.049 Uiso 1 1 calc R B 1 C72 C 0.5023(2) 0.9676(3) 0.46986(16) 0.0353(9) Uani 1 1 d . B 1 C73 C 0.5042(2) 1.0111(3) 0.51948(18) 0.0434(10) Uani 1 1 d . B 1 H73 H 0.5504 1.0326 0.542 0.052 Uiso 1 1 calc R B 1 C74 C 0.4409(3) 1.0238(4) 0.5367(2) 0.0568(13) Uani 1 1 d . B 1 H74 H 0.4445 1.0534 0.5704 0.068 Uiso 1 1 calc R B 1 C75 C 0.3722(3) 0.9931(4) 0.5045(3) 0.0619(14) Uani 1 1 d . B 1 H75 H 0.3288 1.0012 0.516 0.074 Uiso 1 1 calc R B 1 C76 C 0.3687(3) 0.9509(4) 0.4560(2) 0.0562(13) Uani 1 1 d . B 1 H76 H 0.3223 0.9297 0.4336 0.067 Uiso 1 1 calc R B 1 C77 C 0.4321(2) 0.9387(3) 0.43917(19) 0.0419(10) Uani 1 1 d . B 1 H77 H 0.4275 0.9094 0.4053 0.05 Uiso 1 1 calc R B 1 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 0.0311(17) 0.0331(17) 0.0353(18) 0.0006(14) 0.0013(14) -0.0054(13) N2 0.0272(15) 0.0248(15) 0.0334(17) -0.0015(13) 0.0053(13) -0.0046(12) N3 0.0375(17) 0.0257(16) 0.047(2) -0.0033(14) 0.0105(15) -0.0003(13) N4 0.0435(18) 0.0281(15) 0.0277(17) 0.0005(13) 0.0069(14) -0.0030(14) N5 0.050(2) 0.0315(17) 0.0366(19) -0.0026(14) 0.0163(16) -0.0070(15) N6 0.046(2) 0.0391(18) 0.0295(17) -0.0081(14) 0.0087(15) -0.0109(15) C1 0.0327(19) 0.0242(17) 0.030(2) 0.0015(14) 0.0110(16) -0.0038(15) C2 0.037(2) 0.042(2) 0.055(3) 0.000(2) 0.002(2) -0.0094(18) C3 0.052(3) 0.047(3) 0.070(3) -0.008(2) 0.010(3) -0.018(2) C4 0.051(3) 0.0261(19) 0.056(3) -0.0127(18) 0.010(2) -0.0074(18) C5 0.030(2) 0.033(2) 0.059(3) 0.0045(19) 0.010(2) 0.0019(16) C6 0.035(2) 0.045(2) 0.053(3) 0.003(2) 0.017(2) 0.0016(18) C7 0.034(2) 0.038(2) 0.046(3) -0.0016(18) 0.0142(19) -0.0143(17) C8 0.039(2) 0.0259(18) 0.035(2) -0.0017(16) 0.0036(17) 0.0011(15) C9 0.041(2) 0.034(2) 0.032(2) -0.0072(16) 0.0146(18) -0.0062(16) C10 0.053(3) 0.032(2) 0.038(2) 0.0055(17) 0.008(2) -0.0051(18) C11 0.057(3) 0.041(2) 0.040(3) 0.0063(19) 0.007(2) 0.008(2) C12 0.044(2) 0.056(3) 0.037(2) -0.002(2) 0.0094(19) 0.003(2) C13 0.062(3) 0.056(3) 0.042(3) -0.019(2) 0.013(2) -0.026(2) C14 0.062(3) 0.052(3) 0.049(3) -0.021(2) 0.021(2) -0.028(2) C15 0.061(3) 0.040(2) 0.049(3) -0.006(2) 0.024(2) -0.017(2) C16 0.037(2) 0.035(2) 0.037(2) -0.0013(17) 0.0013(18) 0.0063(17) C17 0.032(2) 0.0308(19) 0.031(2) 0.0019(15) 0.0047(17) -0.0003(15) C18 0.030(2) 0.091(4) 0.053(3) 0.008(3) 0.010(2) -0.001(2) C19 0.047(3) 0.085(4) 0.052(3) 0.007(3) 0.026(2) 0.001(2) C20 0.058(3) 0.092(4) 0.038(3) 0.010(3) 0.022(2) 0.012(3) C21 0.042(3) 0.150(6) 0.039(3) 0.008(3) 0.003(2) 0.011(3) C22 0.039(2) 0.106(4) 0.035(3) 0.008(3) 0.013(2) 0.017(3) C23 0.061(3) 0.030(2) 0.044(3) 0.0024(17) 0.026(2) 0.0062(18) C24 0.047(2) 0.0263(19) 0.043(2) 0.0073(17) 0.015(2) 0.0042(17) C25 0.044(2) 0.059(3) 0.040(2) 0.004(2) 0.016(2) 0.008(2) C26 0.051(3) 0.068(3) 0.049(3) 0.005(2) 0.026(2) 0.005(2) C27 0.058(3) 0.062(3) 0.041(3) 0.009(2) 0.014(2) 0.008(2) C28 0.045(3) 0.055(3) 0.054(3) 0.012(2) 0.012(2) 0.008(2) C29 0.050(3) 0.039(2) 0.055(3) 0.007(2) 0.025(2) 0.0110(19) B1 0.035(2) 0.035(2) 0.034(2) 0.0001(19) 0.0111(19) -0.0046(18) B2 0.033(2) 0.028(2) 0.036(2) 0.0026(18) 0.0083(19) -0.0009(17) C30 0.0322(19) 0.040(2) 0.030(2) 0.0015(17) 0.0085(17) 0.0002(17) C31 0.034(2) 0.043(2) 0.035(2) 0.0007(18) 0.0060(18) 0.0030(17) C32 0.052(3) 0.038(2) 0.046(3) -0.0008(19) 0.012(2) 0.000(2) C33 0.041(2) 0.056(3) 0.039(2) 0.008(2) 0.007(2) 0.015(2) C34 0.028(2) 0.059(3) 0.037(2) 0.002(2) 0.0038(17) 0.0054(18) C35 0.035(2) 0.044(2) 0.039(2) -0.0021(18) 0.0096(18) -0.0022(17) C36 0.032(2) 0.0332(19) 0.027(2) 0.0026(16) 0.0020(16) 0.0003(15) C37 0.039(2) 0.044(2) 0.039(2) 0.0015(18) 0.0129(19) -0.0055(18) C38 0.043(2) 0.046(2) 0.047(3) 0.003(2) 0.015(2) -0.0113(19) C39 0.057(3) 0.035(2) 0.054(3) -0.004(2) 0.015(2) -0.017(2) C40 0.063(3) 0.039(2) 0.047(3) -0.006(2) 0.022(2) -0.005(2) C41 0.040(2) 0.038(2) 0.040(2) 0.0031(18) 0.0168(19) -0.0025(17) C42 0.0264(18) 0.034(2) 0.034(2) -0.0002(16) 0.0056(16) -0.0093(15) C43 0.0258(18) 0.038(2) 0.038(2) -0.0010(17) 0.0100(17) -0.0024(16) C44 0.037(2) 0.045(2) 0.039(2) -0.0086(19) 0.0152(18) -0.0104(18) C45 0.049(2) 0.053(3) 0.027(2) -0.0026(19) 0.0068(18) -0.017(2) C46 0.049(3) 0.041(2) 0.037(2) 0.0061(19) 0.005(2) -0.0075(19) C47 0.042(2) 0.032(2) 0.040(2) -0.0015(17) 0.0079(19) -0.0070(17) C48 0.037(2) 0.034(2) 0.034(2) -0.0016(17) 0.0104(17) -0.0084(16) C49 0.038(2) 0.041(2) 0.048(3) 0.0025(19) 0.010(2) -0.0065(18) C50 0.057(3) 0.053(3) 0.058(3) 0.004(2) 0.027(2) -0.014(2) C51 0.036(2) 0.059(3) 0.079(4) -0.014(3) 0.029(2) -0.013(2) C52 0.034(2) 0.045(3) 0.073(3) -0.002(2) 0.017(2) -0.0012(19) C53 0.039(2) 0.041(2) 0.061(3) 0.006(2) 0.016(2) -0.0033(19) C54 0.0288(18) 0.034(2) 0.040(2) -0.0017(17) 0.0130(17) -0.0001(16) C55 0.036(2) 0.037(2) 0.035(2) 0.0023(17) 0.0146(18) 0.0048(17) C56 0.048(2) 0.045(2) 0.041(2) 0.0052(19) 0.022(2) 0.013(2) C57 0.043(2) 0.057(3) 0.037(2) -0.001(2) 0.0091(19) 0.008(2) C58 0.047(3) 0.053(3) 0.039(3) -0.006(2) 0.005(2) -0.004(2) C59 0.044(2) 0.038(2) 0.045(3) 0.0005(19) 0.015(2) -0.0072(18) C60 0.046(2) 0.036(2) 0.028(2) 0.0025(16) 0.0159(18) -0.0029(17) C61 0.056(3) 0.038(2) 0.035(2) 0.0029(18) 0.010(2) 0.0004(19) C62 0.073(3) 0.030(2) 0.045(3) 0.0063(18) 0.016(2) -0.005(2) C63 0.070(3) 0.050(3) 0.044(3) -0.005(2) 0.024(2) -0.026(2) C64 0.045(2) 0.056(3) 0.039(2) -0.005(2) 0.016(2) -0.019(2) C65 0.036(2) 0.044(2) 0.041(2) -0.0005(18) 0.0159(19) -0.0002(17) C66 0.0301(19) 0.031(2) 0.041(2) 0.0014(16) 0.0093(17) -0.0035(15) C67 0.038(2) 0.045(2) 0.041(2) 0.0050(19) 0.0133(19) 0.0031(17) C68 0.039(2) 0.055(3) 0.056(3) 0.023(2) 0.011(2) 0.002(2) C69 0.040(2) 0.038(2) 0.075(4) 0.010(2) 0.014(2) 0.0087(18) C70 0.047(3) 0.033(2) 0.072(4) -0.005(2) 0.017(2) 0.0012(19) C71 0.040(2) 0.036(2) 0.045(3) -0.0049(18) 0.009(2) -0.0008(17) C72 0.036(2) 0.0289(19) 0.041(2) 0.0087(16) 0.0104(18) 0.0030(16) C73 0.048(2) 0.042(2) 0.045(2) 0.0002(19) 0.019(2) 0.0060(19) C74 0.072(3) 0.045(3) 0.067(3) 0.007(2) 0.042(3) 0.012(2) C75 0.050(3) 0.057(3) 0.092(4) 0.018(3) 0.042(3) 0.013(2) C76 0.039(2) 0.045(3) 0.087(4) 0.018(3) 0.021(3) 0.004(2) C77 0.036(2) 0.038(2) 0.053(3) 0.0112(19) 0.013(2) 0.0043(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 N1 C1 1.334(5) . ? N1 C2 1.469(5) . ? N1 C16 1.481(5) . ? N2 C1 1.363(5) . ? N2 C8 1.452(5) . ? N2 C7 1.481(5) . ? N3 C1 1.319(5) . ? N3 C5 1.461(5) . ? N3 C4 1.474(5) . ? N4 C9 1.343(5) . ? N4 C8 1.457(5) . ? N4 C10 1.469(5) . ? N5 C9 1.359(5) . ? N5 C15 1.476(5) . ? N5 C23 1.486(6) . ? N6 C9 1.336(5) . ? N6 C12 1.474(5) . ? N6 C13 1.490(5) . ? C2 C3 1.510(7) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.483(7) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.505(6) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.509(6) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C10 C11 1.499(6) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.514(6) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C14 1.490(7) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.506(6) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.495(5) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C22 1.367(6) . ? C17 C18 1.386(6) . ? C18 C19 1.368(7) . ? C18 H18 0.95 . ? C19 C20 1.360(7) . ? C19 H19 0.95 . ? C20 C21 1.364(7) . ? C20 H20 0.95 . ? C21 C22 1.387(7) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? C23 C24 1.521(6) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 C25 1.380(6) . ? C24 C29 1.385(6) . ? C25 C26 1.389(7) . ? C25 H25 0.95 . ? C26 C27 1.389(7) . ? C26 H26 0.95 . ? C27 C28 1.376(7) . ? C27 H27 0.95 . ? C28 C29 1.373(7) . ? C28 H28 0.95 . ? C29 H29 0.95 . ? B1 C36 1.650(6) . ? B1 C30 1.652(6) . ? B1 C42 1.661(6) . ? B1 C48 1.667(6) . ? B2 C54 1.636(6) . ? B2 C60 1.660(6) . ? B2 C66 1.662(6) . ? B2 C72 1.665(6) . ? C30 C31 1.401(6) . ? C30 C35 1.410(6) . ? C31 C32 1.389(6) . ? C31 H31 0.95 . ? C32 C33 1.386(6) . ? C32 H32 0.95 . ? C33 C34 1.369(6) . ? C33 H33 0.95 . ? C34 C35 1.394(6) . ? C34 H34 0.95 . ? C35 H35 0.95 . ? C36 C37 1.405(6) . ? C36 C41 1.408(6) . ? C37 C38 1.388(6) . ? C37 H37 0.95 . ? C38 C39 1.379(7) . ? C38 H38 0.95 . ? C39 C40 1.369(7) . ? C39 H39 0.95 . ? C40 C41 1.385(6) . ? C40 H40 0.95 . ? C41 H41 0.95 . ? C42 C43 1.394(5) . ? C42 C47 1.406(6) . ? C43 C44 1.397(6) . ? C43 H43 0.95 . ? C44 C45 1.378(6) . ? C44 H44 0.95 . ? C45 C46 1.391(6) . ? C45 H45 0.95 . ? C46 C47 1.388(6) . ? C46 H46 0.95 . ? C47 H47 0.95 . ? C48 C53 1.392(6) . ? C48 C49 1.393(6) . ? C49 C50 1.407(6) . ? C49 H49 0.95 . ? C50 C51 1.373(7) . ? C50 H50 0.95 . ? C51 C52 1.388(7) . ? C51 H51 0.95 . ? C52 C53 1.379(6) . ? C52 H52 0.95 . ? C53 H53 0.95 . ? C54 C55 1.402(6) . ? C54 C59 1.404(6) . ? C55 C56 1.398(6) . ? C55 H55 0.95 . ? C56 C57 1.383(6) . ? C56 H56 0.95 . ? C57 C58 1.378(7) . ? C57 H57 0.95 . ? C58 C59 1.397(6) . ? C58 H58 0.95 . ? C59 H59 0.95 . ? C60 C61 1.398(6) . ? C60 C65 1.405(6) . ? C61 C62 1.387(6) . ? C61 H61 0.95 . ? C62 C63 1.392(7) . ? C62 H62 0.95 . ? C63 C64 1.367(7) . ? C63 H63 0.95 . ? C64 C65 1.381(6) . ? C64 H64 0.95 . ? C65 H65 0.95 . ? C66 C71 1.403(6) . ? C66 C67 1.406(6) . ? C67 C68 1.388(6) . ? C67 H67 0.95 . ? C68 C69 1.376(7) . ? C68 H68 0.95 . ? C69 C70 1.379(7) . ? C69 H69 0.95 . ? C70 C71 1.385(6) . ? C70 H70 0.95 . ? C71 H71 0.95 . ? C72 C77 1.399(6) . ? C72 C73 1.412(6) . ? C73 C74 1.395(6) . ? C73 H73 0.95 . ? C74 C75 1.397(8) . ? C74 H74 0.95 . ? C75 C76 1.373(8) . ? C75 H75 0.95 . ? C76 C77 1.390(6) . ? C76 H76 0.95 . ? C77 H77 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 C2 120.0(3) . . ? C1 N1 C16 122.4(3) . . ? C2 N1 C16 114.2(3) . . ? C1 N2 C8 121.5(3) . . ? C1 N2 C7 119.6(3) . . ? C8 N2 C7 118.4(3) . . ? C1 N3 C5 118.0(3) . . ? C1 N3 C4 120.4(3) . . ? C5 N3 C4 121.5(3) . . ? C9 N4 C8 123.0(3) . . ? C9 N4 C10 119.0(3) . . ? C8 N4 C10 116.9(3) . . ? C9 N5 C15 115.1(3) . . ? C9 N5 C23 122.9(3) . . ? C15 N5 C23 114.5(3) . . ? C9 N6 C12 124.3(3) . . ? C9 N6 C13 123.0(4) . . ? C12 N6 C13 112.5(3) . . ? N3 C1 N1 122.2(3) . . ? N3 C1 N2 117.2(3) . . ? N1 C1 N2 120.5(3) . . ? N1 C2 C3 112.6(3) . . ? N1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 109.0(4) . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N3 C4 C3 106.8(4) . . ? N3 C4 H4A 110.4 . . ? C3 C4 H4A 110.4 . . ? N3 C4 H4B 110.4 . . ? C3 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? N3 C5 C6 107.6(3) . . ? N3 C5 H5A 110.2 . . ? C6 C5 H5A 110.2 . . ? N3 C5 H5B 110.2 . . ? C6 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? C5 C6 C7 110.5(3) . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C6 111.6(3) . . ? N2 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? N2 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108 . . ? N2 C8 N4 112.1(3) . . ? N2 C8 H8A 109.2 . . ? N4 C8 H8A 109.2 . . ? N2 C8 H8B 109.2 . . ? N4 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N6 C9 N4 118.8(3) . . ? N6 C9 N5 119.9(3) . . ? N4 C9 N5 121.3(4) . . ? N4 C10 C11 109.0(4) . . ? N4 C10 H10A 109.9 . . ? C11 C10 H10A 109.9 . . ? N4 C10 H10B 109.9 . . ? C11 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? C10 C11 C12 108.3(4) . . ? C10 C11 H11A 110 . . ? C12 C11 H11A 110 . . ? C10 C11 H11B 110 . . ? C12 C11 H11B 110 . . ? H11A C11 H11B 108.4 . . ? N6 C12 C11 112.0(3) . . ? N6 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? N6 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 N6 112.1(4) . . ? C14 C13 H13A 109.2 . . ? N6 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? N6 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 107.6(4) . . ? C13 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? C13 C14 H14B 110.2 . . ? C15 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? N5 C15 C14 108.6(3) . . ? N5 C15 H15A 110 . . ? C14 C15 H15A 110 . . ? N5 C15 H15B 110 . . ? C14 C15 H15B 110 . . ? H15A C15 H15B 108.3 . . ? N1 C16 C17 112.7(3) . . ? N1 C16 H16A 109 . . ? C17 C16 H16A 109 . . ? N1 C16 H16B 109 . . ? C17 C16 H16B 109 . . ? H16A C16 H16B 107.8 . . ? C22 C17 C18 116.7(4) . . ? C22 C17 C16 121.5(4) . . ? C18 C17 C16 121.7(4) . . ? C19 C18 C17 122.2(4) . . ? C19 C18 H18 118.9 . . ? C17 C18 H18 118.9 . . ? C20 C19 C18 120.0(4) . . ? C20 C19 H19 120 . . ? C18 C19 H19 120 . . ? C19 C20 C21 119.0(5) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C22 120.6(5) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C17 C22 C21 121.2(4) . . ? C17 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? N5 C23 C24 114.2(3) . . ? N5 C23 H23A 108.7 . . ? C24 C23 H23A 108.7 . . ? N5 C23 H23B 108.7 . . ? C24 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C25 C24 C29 117.3(4) . . ? C25 C24 C23 123.2(4) . . ? C29 C24 C23 119.3(4) . . ? C24 C25 C26 121.5(4) . . ? C24 C25 H25 119.2 . . ? C26 C25 H25 119.2 . . ? C25 C26 C27 119.9(4) . . ? C25 C26 H26 120 . . ? C27 C26 H26 120 . . ? C28 C27 C26 118.8(5) . . ? C28 C27 H27 120.6 . . ? C26 C27 H27 120.6 . . ? C29 C28 C27 120.6(4) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C24 121.9(4) . . ? C28 C29 H29 119.1 . . ? C24 C29 H29 119.1 . . ? C36 B1 C30 110.0(3) . . ? C36 B1 C42 106.9(3) . . ? C30 B1 C42 110.3(3) . . ? C36 B1 C48 109.9(3) . . ? C30 B1 C48 111.2(3) . . ? C42 B1 C48 108.4(3) . . ? C54 B2 C60 111.0(3) . . ? C54 B2 C66 111.6(3) . . ? C60 B2 C66 107.5(3) . . ? C54 B2 C72 108.3(3) . . ? C60 B2 C72 109.0(3) . . ? C66 B2 C72 109.5(3) . . ? C31 C30 C35 114.1(4) . . ? C31 C30 B1 122.3(3) . . ? C35 C30 B1 123.6(3) . . ? C32 C31 C30 123.3(4) . . ? C32 C31 H31 118.4 . . ? C30 C31 H31 118.4 . . ? C33 C32 C31 120.1(4) . . ? C33 C32 H32 120 . . ? C31 C32 H32 120 . . ? C34 C33 C32 119.1(4) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? C33 C34 C35 120.1(4) . . ? C33 C34 H34 120 . . ? C35 C34 H34 120 . . ? C34 C35 C30 123.2(4) . . ? C34 C35 H35 118.4 . . ? C30 C35 H35 118.4 . . ? C37 C36 C41 114.8(3) . . ? C37 C36 B1 120.1(3) . . ? C41 C36 B1 125.0(3) . . ? C38 C37 C36 123.1(4) . . ? C38 C37 H37 118.4 . . ? C36 C37 H37 118.4 . . ? C39 C38 C37 119.6(4) . . ? C39 C38 H38 120.2 . . ? C37 C38 H38 120.2 . . ? C40 C39 C38 119.4(4) . . ? C40 C39 H39 120.3 . . ? C38 C39 H39 120.3 . . ? C39 C40 C41 120.9(4) . . ? C39 C40 H40 119.5 . . ? C41 C40 H40 119.5 . . ? C40 C41 C36 122.2(4) . . ? C40 C41 H41 118.9 . . ? C36 C41 H41 118.9 . . ? C43 C42 C47 114.7(4) . . ? C43 C42 B1 124.8(3) . . ? C47 C42 B1 120.5(3) . . ? C42 C43 C44 122.8(4) . . ? C42 C43 H43 118.6 . . ? C44 C43 H43 118.6 . . ? C45 C44 C43 120.6(4) . . ? C45 C44 H44 119.7 . . ? C43 C44 H44 119.7 . . ? C44 C45 C46 118.5(4) . . ? C44 C45 H45 120.8 . . ? C46 C45 H45 120.8 . . ? C47 C46 C45 119.9(4) . . ? C47 C46 H46 120 . . ? C45 C46 H46 120 . . ? C46 C47 C42 123.3(4) . . ? C46 C47 H47 118.4 . . ? C42 C47 H47 118.4 . . ? C53 C48 C49 114.3(4) . . ? C53 C48 B1 121.2(3) . . ? C49 C48 B1 124.5(4) . . ? C48 C49 C50 122.7(4) . . ? C48 C49 H49 118.6 . . ? C50 C49 H49 118.6 . . ? C51 C50 C49 120.4(4) . . ? C51 C50 H50 119.8 . . ? C49 C50 H50 119.8 . . ? C50 C51 C52 118.5(4) . . ? C50 C51 H51 120.8 . . ? C52 C51 H51 120.8 . . ? C53 C52 C51 119.8(4) . . ? C53 C52 H52 120.1 . . ? C51 C52 H52 120.1 . . ? C52 C53 C48 124.4(4) . . ? C52 C53 H53 117.8 . . ? C48 C53 H53 117.8 . . ? C55 C54 C59 114.0(4) . . ? C55 C54 B2 123.7(3) . . ? C59 C54 B2 121.8(3) . . ? C56 C55 C54 123.1(4) . . ? C56 C55 H55 118.4 . . ? C54 C55 H55 118.4 . . ? C57 C56 C55 120.2(4) . . ? C57 C56 H56 119.9 . . ? C55 C56 H56 119.9 . . ? C58 C57 C56 119.1(4) . . ? C58 C57 H57 120.5 . . ? C56 C57 H57 120.5 . . ? C57 C58 C59 119.6(4) . . ? C57 C58 H58 120.2 . . ? C59 C58 H58 120.2 . . ? C58 C59 C54 123.8(4) . . ? C58 C59 H59 118.1 . . ? C54 C59 H59 118.1 . . ? C61 C60 C65 114.1(4) . . ? C61 C60 B2 122.0(4) . . ? C65 C60 B2 123.9(4) . . ? C62 C61 C60 123.6(4) . . ? C62 C61 H61 118.2 . . ? C60 C61 H61 118.2 . . ? C61 C62 C63 119.5(4) . . ? C61 C62 H62 120.3 . . ? C63 C62 H62 120.3 . . ? C64 C63 C62 119.0(4) . . ? C64 C63 H63 120.5 . . ? C62 C63 H63 120.5 . . ? C63 C64 C65 120.5(4) . . ? C63 C64 H64 119.7 . . ? C65 C64 H64 119.7 . . ? C64 C65 C60 123.3(4) . . ? C64 C65 H65 118.4 . . ? C60 C65 H65 118.4 . . ? C71 C66 C67 114.7(4) . . ? C71 C66 B2 123.9(4) . . ? C67 C66 B2 121.3(3) . . ? C68 C67 C66 122.4(4) . . ? C68 C67 H67 118.8 . . ? C66 C67 H67 118.8 . . ? C69 C68 C67 121.0(5) . . ? C69 C68 H68 119.5 . . ? C67 C68 H68 119.5 . . ? C68 C69 C70 118.3(4) . . ? C68 C69 H69 120.9 . . ? C70 C69 H69 120.9 . . ? C69 C70 C71 120.7(4) . . ? C69 C70 H70 119.7 . . ? C71 C70 H70 119.7 . . ? C70 C71 C66 122.9(4) . . ? C70 C71 H71 118.5 . . ? C66 C71 H71 118.5 . . ? C77 C72 C73 114.9(4) . . ? C77 C72 B2 124.1(4) . . ? C73 C72 B2 120.9(4) . . ? C74 C73 C72 122.5(4) . . ? C74 C73 H73 118.7 . . ? C72 C73 H73 118.7 . . ? C73 C74 C75 120.2(5) . . ? C73 C74 H74 119.9 . . ? C75 C74 H74 119.9 . . ? C76 C75 C74 118.6(4) . . ? C76 C75 H75 120.7 . . ? C74 C75 H75 120.7 . . ? C75 C76 C77 120.8(5) . . ? C75 C76 H76 119.6 . . ? C77 C76 H76 119.6 . . ? C76 C77 C72 123.0(5) . . ? C76 C77 H77 118.5 . . ? C72 C77 H77 118.5 . . ? #===END # Attachment 'Revised CIF B715209D.cif' data_(1)-feb807 _database_code_depnum_ccdc_archive 'CCDC 662882' _audit_creation_date 2007-02-13T09:57:00-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H26 N6' _chemical_formula_sum 'C15 H26 N6' _chemical_formula_weight 290.42 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 31 2 1' _symmetry_space_group_name_Hall 'P 31 2"' _symmetry_Int_Tables_number 152 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' 'y, x, -z' '-x+y, -x, z+2/3' '-x, -x+y, -z+1/3' 'x-y, -y, -z+2/3' _cell_length_a 8.6890(5) _cell_length_b 8.6890(5) _cell_length_c 17.1794(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 1123.25(10) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10677 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.733 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.816843E-1 _diffrn_orient_matrix_ub_12 0.507396E-1 _diffrn_orient_matrix_ub_13 0.45641E-1 _diffrn_orient_matrix_ub_21 0.104712 _diffrn_orient_matrix_ub_22 0.499285E-1 _diffrn_orient_matrix_ub_23 -0.358208E-1 _diffrn_orient_matrix_ub_31 -0.4835E-2 _diffrn_orient_matrix_ub_32 0.112218 _diffrn_orient_matrix_ub_33 -0.46991E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_unetI/netI 0.0279 _diffrn_reflns_number 7330 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 26.7 _diffrn_reflns_theta_full 26.7 _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _reflns_number_total 923 _reflns_number_gt 838 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Friedel pairs were merged (C,H,and N atoms only, and Mo-Kalpha radiation) 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^)+(0.0440P)^2^+0.1813P] 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 923 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(3) _refine_diff_density_max 0.144 _refine_diff_density_min -0.131 _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 N1 N 0.83842(19) 0.1036(2) 0.16456(7) 0.0234(4) Uani 1 1 d . . . N2 N 0.7970(2) 0.14179(19) 0.03452(8) 0.0264(4) Uani 1 1 d . . . N3 N 0.6125(2) -0.1354(2) 0.09557(8) 0.0287(4) Uani 1 1 d . . . C1 C 0.7501(2) 0.0380(2) 0.09410(9) 0.0212(4) Uani 1 1 d . . . C2 C 0.8196(3) -0.0167(3) 0.22732(9) 0.0318(4) Uani 1 1 d . . . H2A H 0.8692 0.0513 0.276 0.038 Uiso 1 1 calc R . . H2B H 0.8862 -0.0784 0.2145 0.038 Uiso 1 1 calc R . . C3 C 0.6255(3) -0.1512(3) 0.23856(10) 0.0358(5) Uani 1 1 d . . . H3A H 0.6114 -0.2345 0.2809 0.043 Uiso 1 1 calc R . . H3B H 0.5592 -0.0902 0.253 0.043 Uiso 1 1 calc R . . C4 C 0.5542(3) -0.2513(3) 0.16348(10) 0.0366(5) Uani 1 1 d . . . H4A H 0.5937 -0.3397 0.1581 0.044 Uiso 1 1 calc R . . H4B H 0.4227 -0.3167 0.1654 0.044 Uiso 1 1 calc R . . C5 C 0.5242(3) -0.2238(3) 0.02320(10) 0.0370(5) Uani 1 1 d . . . H5A H 0.4063 -0.2324 0.0206 0.044 Uiso 1 1 calc R . . H5B H 0.5052 -0.346 0.0229 0.044 Uiso 1 1 calc R . . C6 C 0.6318(3) -0.1249(3) -0.04721(9) 0.0336(5) Uani 1 1 d . . . H6A H 0.5586 -0.1705 -0.0949 0.04 Uiso 1 1 calc R . . H6B H 0.7361 -0.1414 -0.0526 0.04 Uiso 1 1 calc R . . C7 C 0.6919(3) 0.0697(3) -0.03623(9) 0.0316(5) Uani 1 1 d . . . H7A H 0.7638 0.1375 -0.0817 0.038 Uiso 1 1 calc R . . H7B H 0.5863 0.0848 -0.0337 0.038 Uiso 1 1 calc R . . C8 C 1 0.2767(3) 0.1667 0.0239(5) Uani 1 2 d S . . H8A H 0.9968 0.3422 0.2132 0.029 Uiso 0.5 1 calc PR . . H8B H 1.0032 0.3454 0.1201 0.029 Uiso 0.5 1 calc PR . . 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 0.0232(8) 0.0253(8) 0.0202(6) 0.0015(6) -0.0023(5) 0.0108(7) N2 0.0306(9) 0.0275(8) 0.0213(6) -0.0011(6) -0.0082(6) 0.0145(7) N3 0.0265(8) 0.0263(8) 0.0274(7) -0.0023(6) -0.0010(6) 0.0088(7) C1 0.0201(9) 0.0236(9) 0.0238(7) -0.0036(7) -0.0012(6) 0.0138(7) C2 0.0340(10) 0.0350(10) 0.0229(8) 0.0093(7) 0.0013(7) 0.0146(9) C3 0.0353(11) 0.0381(11) 0.0305(9) 0.0089(8) 0.0115(8) 0.0156(9) C4 0.0308(11) 0.0296(10) 0.0410(10) 0.0042(9) 0.0064(9) 0.0088(9) C5 0.0292(10) 0.0357(12) 0.0407(10) -0.0123(9) -0.0089(9) 0.0121(9) C6 0.0377(11) 0.0388(12) 0.0287(8) -0.0126(8) -0.0111(8) 0.0225(9) C7 0.0386(11) 0.0381(11) 0.0237(8) -0.0056(7) -0.0096(8) 0.0233(9) C8 0.0272(13) 0.0227(9) 0.0233(11) -0.0023(5) -0.0047(10) 0.0136(6) #----------------------------------------------------------------------------# # 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 1.3936(19) . ? N1 C2 1.453(2) . ? N1 C8 1.4568(19) . ? N2 C1 1.288(2) . ? N2 C7 1.460(2) . ? N3 C1 1.378(2) . ? N3 C4 1.457(2) . ? N3 C5 1.461(2) . ? C2 C3 1.508(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.505(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.508(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.512(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 N1 1.4568(19) 5_765 ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? 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 C2 120.61(14) . . ? C1 N1 C8 119.57(11) . . ? C2 N1 C8 115.34(13) . . ? C1 N2 C7 116.75(15) . . ? C1 N3 C4 125.59(14) . . ? C1 N3 C5 119.97(14) . . ? C4 N3 C5 114.13(15) . . ? N2 C1 N3 125.30(15) . . ? N2 C1 N1 119.13(15) . . ? N3 C1 N1 115.53(14) . . ? N1 C2 C3 109.41(15) . . ? N1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C2 108.40(14) . . ? C4 C3 H3A 110 . . ? C2 C3 H3A 110 . . ? C4 C3 H3B 110 . . ? C2 C3 H3B 110 . . ? H3A C3 H3B 108.4 . . ? N3 C4 C3 112.74(16) . . ? N3 C4 H4A 109 . . ? C3 C4 H4A 109 . . ? N3 C4 H4B 109 . . ? C3 C4 H4B 109 . . ? H4A C4 H4B 107.8 . . ? N3 C5 C6 111.73(15) . . ? N3 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N3 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 107.84(15) . . ? C5 C6 H6A 110.1 . . ? C7 C6 H6A 110.1 . . ? C5 C6 H6B 110.1 . . ? C7 C6 H6B 110.1 . . ? H6A C6 H6B 108.5 . . ? N2 C7 C6 112.07(14) . . ? N2 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N2 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N1 C8 N1 113.2(2) . 5_765 ? N1 C8 H8A 108.9 . . ? N1 C8 H8A 108.9 5_765 . ? N1 C8 H8B 108.9 . . ? N1 C8 H8B 108.9 5_765 . ? H8A C8 H8B 107.7 . . ?