# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Martyn Coles' 'Peter B Hitchcock' 'Majid S Khalaf' 'Sarah H Oakley' _publ_contact_author_name 'Martyn Coles' _publ_contact_author_email M.P.COLES@SUSSEX.AC.UK _publ_section_title ; A strategy for the propagation of hydrogen-bonding in bicyclic guanidinium salts ; _publ_requested_category FO # Attachment 'Combined.cif' data_1a-dec503 _database_code_depnum_ccdc_archive 'CCDC 693294' _audit_creation_date 2003-12-05T11:27:04-00:00 _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 'C7 H14 Cl1 N3' _chemical_formula_sum 'C7 H14 Cl1 N3' _chemical_formula_weight 175.66 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 6.7679(2) _cell_length_b 8.6829(4) _cell_length_c 14.9689(5) _cell_angle_alpha 90 _cell_angle_beta 100.679(2) _cell_angle_gamma 90 _cell_volume 864.41(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4378 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.35 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.382 _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 -0.270087E-1 _diffrn_orient_matrix_ub_12 0.112083 _diffrn_orient_matrix_ub_13 0.7326E-2 _diffrn_orient_matrix_ub_21 -0.1063 _diffrn_orient_matrix_ub_22 -0.263929E-1 _diffrn_orient_matrix_ub_23 0.357924E-1 _diffrn_orient_matrix_ub_31 0.102854 _diffrn_orient_matrix_ub_32 0.21549E-2 _diffrn_orient_matrix_ub_33 0.573311E-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 0.05 _diffrn_reflns_av_unetI/netI 0.0334 _diffrn_reflns_number 6659 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _reflns_number_total 1943 _reflns_number_gt 1756 _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 on N were refined ; others riding. 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^)+(0.0414P)^2^+0.2947P] 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 1943 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.083 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.238 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 Cl Cl 0.14022(5) 0.31485(4) 0.40753(2) 0.03066(13) Uani 1 1 d . . . N1 N 0.38735(16) 0.39713(13) 0.60905(8) 0.0257(3) Uani 1 1 d . . . H1 H 0.299(3) 0.395(2) 0.5616(13) 0.035(4) Uiso 1 1 d . . . N2 N 0.55803(16) 0.23522(14) 0.52889(8) 0.0263(3) Uani 1 1 d . . . H2 H 0.452(3) 0.245(2) 0.4849(13) 0.039(5) Uiso 1 1 d . . . N3 N 0.71421(15) 0.32130(11) 0.67132(7) 0.0201(2) Uani 1 1 d . . . C1 C 0.55667(17) 0.32007(13) 0.60295(8) 0.0196(3) Uani 1 1 d . . . C2 C 0.38339(19) 0.51365(15) 0.67867(9) 0.0271(3) Uani 1 1 d . . . H2B H 0.2434 0.5315 0.6869 0.033 Uiso 1 1 calc R . . H2A H 0.4381 0.612 0.6602 0.033 Uiso 1 1 calc R . . C3 C 0.5098(2) 0.45703(16) 0.76664(9) 0.0275(3) Uani 1 1 d . . . H3B H 0.448 0.3637 0.7877 0.033 Uiso 1 1 calc R . . H3A H 0.5164 0.5373 0.8141 0.033 Uiso 1 1 calc R . . C4 C 0.72024(18) 0.42004(15) 0.75125(8) 0.0242(3) Uani 1 1 d . . . H4B H 0.7913 0.517 0.7426 0.029 Uiso 1 1 calc R . . H4A H 0.7962 0.3674 0.8056 0.029 Uiso 1 1 calc R . . C5 C 0.90926(18) 0.26494(16) 0.65509(9) 0.0266(3) Uani 1 1 d . . . H5B H 0.9981 0.2422 0.7139 0.032 Uiso 1 1 calc R . . H5A H 0.9745 0.3455 0.6238 0.032 Uiso 1 1 calc R . . C6 C 0.88045(19) 0.12071(17) 0.59728(9) 0.0281(3) Uani 1 1 d . . . H6B H 1.0111 0.0877 0.583 0.034 Uiso 1 1 calc R . . H6A H 0.8288 0.0366 0.6312 0.034 Uiso 1 1 calc R . . C7 C 0.7334(2) 0.15198(17) 0.51009(9) 0.0291(3) Uani 1 1 d . . . H7B H 0.8002 0.2137 0.4686 0.035 Uiso 1 1 calc R . . H7A H 0.6899 0.0533 0.4796 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl 0.02472(18) 0.0371(2) 0.0271(2) 0.00277(13) -0.00323(13) -0.00270(12) N1 0.0182(5) 0.0313(6) 0.0256(6) -0.0048(5) -0.0012(4) 0.0040(4) N2 0.0212(5) 0.0349(6) 0.0212(5) -0.0050(5) -0.0003(4) 0.0037(5) N3 0.0174(5) 0.0216(5) 0.0201(5) -0.0021(4) 0.0008(4) 0.0010(4) C1 0.0180(5) 0.0197(6) 0.0208(6) 0.0026(5) 0.0028(4) -0.0021(4) C2 0.0250(6) 0.0233(6) 0.0321(7) -0.0028(5) 0.0028(5) 0.0041(5) C3 0.0303(6) 0.0263(6) 0.0263(7) -0.0042(5) 0.0067(5) 0.0038(5) C4 0.0248(6) 0.0246(6) 0.0213(6) -0.0032(5) -0.0007(5) -0.0001(5) C5 0.0167(5) 0.0324(7) 0.0296(7) -0.0016(6) 0.0012(5) 0.0046(5) C6 0.0258(6) 0.0301(7) 0.0290(7) -0.0005(5) 0.0063(5) 0.0074(5) C7 0.0264(6) 0.0367(7) 0.0250(7) -0.0045(6) 0.0071(5) 0.0038(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 1.3446(15) . ? N1 C2 1.4563(17) . ? N2 C1 1.3326(17) . ? N2 C7 1.4610(16) . ? N3 C1 1.3341(16) . ? N3 C4 1.4663(16) . ? N3 C5 1.4697(15) . ? C2 C3 1.5133(19) . ? C3 C4 1.5185(17) . ? C5 C6 1.514(2) . ? C6 C7 1.5119(19) . ? 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 121.55(11) . . ? C1 N2 C7 124.39(11) . . ? C1 N3 C4 121.88(10) . . ? C1 N3 C5 119.02(10) . . ? C4 N3 C5 116.07(10) . . ? N2 C1 N3 120.99(11) . . ? N2 C1 N1 117.96(11) . . ? N3 C1 N1 120.93(11) . . ? N1 C2 C3 108.33(10) . . ? C2 C3 C4 109.37(11) . . ? N3 C4 C3 111.24(10) . . ? N3 C5 C6 110.21(10) . . ? C7 C6 C5 109.83(12) . . ? N2 C7 C6 110.54(11) . . ? #===END data_1b-aug503 _database_code_depnum_ccdc_archive 'CCDC 693295' _audit_creation_date 2003-08-20T13:46:46-00:00 _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 'C7 H14 Br1 N3' _chemical_formula_sum 'C7 H14 Br1 N3' _chemical_formula_weight 220.12 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 6.8903(3) _cell_length_b 8.8030(4) _cell_length_c 15.1958(8) _cell_angle_alpha 90 _cell_angle_beta 99.411(2) _cell_angle_gamma 90 _cell_volume 909.30(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9915 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 24.713 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.464 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.3958 _exptl_absorpt_correction_T_max 0.5781 #----------------------------------------------------------------------------# # 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 -0.75303E-2 _diffrn_orient_matrix_ub_12 -0.480842E-1 _diffrn_orient_matrix_ub_13 0.589679E-1 _diffrn_orient_matrix_ub_21 0.11782 _diffrn_orient_matrix_ub_22 0.594907E-1 _diffrn_orient_matrix_ub_23 0.278455E-1 _diffrn_orient_matrix_ub_31 -0.877707E-1 _diffrn_orient_matrix_ub_32 0.839832E-1 _diffrn_orient_matrix_ub_33 0.140371E-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 0.1095 _diffrn_reflns_av_unetI/netI 0.0591 _diffrn_reflns_number 9052 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.7 _diffrn_reflns_theta_max 24.68 _diffrn_reflns_theta_full 24.68 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 1531 _reflns_number_gt 1201 _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 ; H atoms on nitrogen were refined; others were in riding mode. 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^)+(0.0423P)^2^+2.1938P] 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 1531 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.025 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.123 #----------------------------------------------------------------------------# # 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' Br Br -0.2901 2.4595 '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 Br Br 0.14405(8) 0.31741(7) 0.40961(4) 0.0321(2) Uani 1 1 d . . . N1 N 0.3959(7) 0.3909(5) 0.6180(3) 0.0269(11) Uani 1 1 d . . . H1 H 0.297(9) 0.385(7) 0.574(4) 0.039(18) Uiso 1 1 d . . . N2 N 0.5653(7) 0.2335(6) 0.5376(3) 0.0306(12) Uani 1 1 d . . . H2 H 0.473(9) 0.251(7) 0.495(4) 0.029(17) Uiso 1 1 d . . . N3 N 0.7158(6) 0.3177(5) 0.6756(3) 0.0233(10) Uani 1 1 d . . . C1 C 0.5629(7) 0.3172(6) 0.6104(3) 0.0217(11) Uani 1 1 d . . . C2 C 0.3912(8) 0.5054(6) 0.6868(4) 0.0304(14) Uani 1 1 d . . . H2B H 0.2542 0.5219 0.6966 0.037 Uiso 1 1 calc R . . H2A H 0.4434 0.6029 0.6682 0.037 Uiso 1 1 calc R . . C3 C 0.5153(8) 0.4500(7) 0.7713(4) 0.0311(14) Uani 1 1 d . . . H3B H 0.5208 0.5288 0.8181 0.037 Uiso 1 1 calc R . . H3A H 0.4553 0.3576 0.7925 0.037 Uiso 1 1 calc R . . C4 C 0.7198(8) 0.4146(6) 0.7551(4) 0.0266(13) Uani 1 1 d . . . H4B H 0.7895 0.5106 0.7467 0.032 Uiso 1 1 calc R . . H4A H 0.7931 0.3621 0.8079 0.032 Uiso 1 1 calc R . . C5 C 0.9079(8) 0.2632(7) 0.6581(4) 0.0291(13) Uani 1 1 d . . . H5B H 0.9939 0.2398 0.7153 0.035 Uiso 1 1 calc R . . H5A H 0.9722 0.3436 0.6275 0.035 Uiso 1 1 calc R . . C6 C 0.8813(8) 0.1221(7) 0.6005(4) 0.0299(14) Uani 1 1 d . . . H6B H 1.0095 0.0914 0.5847 0.036 Uiso 1 1 calc R . . H6A H 0.8325 0.0378 0.6341 0.036 Uiso 1 1 calc R . . C7 C 0.7369(8) 0.1525(7) 0.5167(4) 0.0335(15) Uani 1 1 d . . . H7B H 0.8011 0.214 0.4751 0.04 Uiso 1 1 calc R . . H7A H 0.6948 0.0551 0.4871 0.04 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.0305(4) 0.0351(4) 0.0286(4) 0.0029(3) -0.0012(2) -0.0030(3) N1 0.022(3) 0.032(3) 0.026(3) -0.005(2) 0.000(2) 0.002(2) N2 0.030(3) 0.037(3) 0.023(3) -0.003(2) -0.001(2) 0.003(2) N3 0.025(2) 0.023(2) 0.022(2) -0.001(2) 0.0038(19) -0.001(2) C1 0.025(3) 0.020(3) 0.021(3) 0.000(3) 0.004(2) -0.003(2) C2 0.027(3) 0.025(3) 0.040(4) -0.006(3) 0.006(3) -0.001(2) C3 0.039(4) 0.030(3) 0.025(3) -0.007(3) 0.006(3) 0.000(3) C4 0.035(3) 0.023(3) 0.020(3) -0.002(2) 0.002(2) 0.001(2) C5 0.019(3) 0.035(3) 0.034(3) 0.000(3) 0.005(2) 0.003(2) C6 0.030(3) 0.030(3) 0.031(3) -0.002(3) 0.010(3) 0.009(3) C7 0.031(3) 0.039(4) 0.034(3) -0.002(3) 0.012(3) 0.000(3) #----------------------------------------------------------------------------# # 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 1.342(7) . ? N1 C2 1.457(7) . ? N2 C1 1.330(7) . ? N2 C7 1.460(8) . ? N3 C1 1.323(7) . ? N3 C5 1.473(7) . ? N3 C4 1.476(7) . ? C2 C3 1.503(8) . ? C3 C4 1.502(8) . ? C5 C6 1.513(8) . ? C6 C7 1.506(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 121.1(5) . . ? C1 N2 C7 124.9(5) . . ? C1 N3 C5 119.5(4) . . ? C1 N3 C4 121.4(4) . . ? C5 N3 C4 116.0(4) . . ? N3 C1 N2 120.5(5) . . ? N3 C1 N1 121.5(5) . . ? N2 C1 N1 117.8(5) . . ? N1 C2 C3 108.2(5) . . ? C4 C3 C2 110.2(5) . . ? N3 C4 C3 111.2(5) . . ? N3 C5 C6 110.1(4) . . ? C7 C6 C5 110.1(5) . . ? N2 C7 C6 110.4(5) . . ? #===END data_1c-jan708 _database_code_depnum_ccdc_archive 'CCDC 693296' _audit_creation_date 2008-06-27T07:07:33-00:00 _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 'C24 H20 B, C7 H14 N3' _chemical_formula_sum 'C31 H34 B N3' _chemical_formula_weight 459.42 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41 21 2' _symmetry_space_group_name_Hall 'P 4abw 2nw' _symmetry_Int_Tables_number 92 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z+3/4' '-x, -y, z+1/2' '-x+1/2, y+1/2, -z+1/4' 'y, x, -z' 'y+1/2, -x+1/2, z+3/4' '-y+1/2, x+1/2, z+1/4' '-y, -x, -z+1/2' _cell_length_a 9.64790(10) _cell_length_b 9.64790(10) _cell_length_c 27.5887(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2568.01(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 30084 _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 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _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 -0.991369E-1 _diffrn_orient_matrix_ub_12 0.100539E-1 _diffrn_orient_matrix_ub_13 -0.99774E-2 _diffrn_orient_matrix_ub_21 -0.290154E-1 _diffrn_orient_matrix_ub_22 -0.39543E-2 _diffrn_orient_matrix_ub_23 0.03477 _diffrn_orient_matrix_ub_31 0.85558E-2 _diffrn_orient_matrix_ub_32 0.103085 _diffrn_orient_matrix_ub_33 0.23069E-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 0.0407 _diffrn_reflns_av_unetI/netI 0.0121 _diffrn_reflns_number 35609 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 1531 _reflns_number_gt 1460 _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 ; The thermal ellipsoids of the annular methylene groups in the [hppH2] cation are abnormally large indicating possible disorder. However, no rational model could be discovered and so the atoms were left as they were. 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^)+(0.0683P)^2^+1.4445P] 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 1531 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.298 _refine_diff_density_min -0.31 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # 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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C5 C -0.0008(3) 0.9769(2) 0.04660(8) 0.0272(5) Uani 1 1 d . . . C6 C 0.0695(3) 0.8729(3) 0.07164(8) 0.0340(6) Uani 1 1 d . . . H6 H 0.163 0.8538 0.0632 0.041 Uiso 1 1 calc R . . C7 C 0.0078(3) 0.7958(3) 0.10855(9) 0.0411(6) Uani 1 1 d . . . H7 H 0.0598 0.726 0.1247 0.049 Uiso 1 1 calc R . . C8 C -0.1275(3) 0.8198(3) 0.12175(10) 0.0435(7) Uani 1 1 d . . . H8 H -0.1692 0.7681 0.1472 0.052 Uiso 1 1 calc R . . C9 C -0.2014(3) 0.9201(3) 0.09749(10) 0.0433(7) Uani 1 1 d . . . H9 H -0.2955 0.9368 0.1058 0.052 Uiso 1 1 calc R . . C10 C -0.1390(3) 0.9971(3) 0.06090(9) 0.0352(6) Uani 1 1 d . . . H10 H -0.1921 1.0663 0.0449 0.042 Uiso 1 1 calc R . . C11 C 0.0407(3) 1.2308(2) 0.00508(8) 0.0286(5) Uani 1 1 d . . . C12 C 0.0013(3) 1.2984(3) 0.04773(9) 0.0434(7) Uani 1 1 d . . . H12 H -0.0163 1.2446 0.0759 0.052 Uiso 1 1 calc R . . C13 C -0.0131(4) 1.4426(3) 0.05044(11) 0.0566(9) Uani 1 1 d . . . H13 H -0.0418 1.4841 0.08 0.068 Uiso 1 1 calc R . . C14 C 0.0139(4) 1.5246(3) 0.01100(10) 0.0488(8) Uani 1 1 d . . . H14 H 0.0037 1.6224 0.0129 0.059 Uiso 1 1 calc R . . C15 C 0.0561(3) 1.4625(3) -0.03166(10) 0.0395(6) Uani 1 1 d . . . H15 H 0.0757 1.5177 -0.0593 0.047 Uiso 1 1 calc R . . C16 C 0.0699(3) 1.3192(3) -0.03406(9) 0.0334(6) Uani 1 1 d . . . H16 H 0.1007 1.2791 -0.0636 0.04 Uiso 1 1 calc R . . B B 0.0624(3) 1.0624(3) 0 0.0274(8) Uani 1 2 d S . . N1 N 0.3548(3) 0.4578(3) 0.03260(9) 0.0505(7) Uani 1 1 d . . . H1 H 0.2934 0.3905 0.0319 0.061 Uiso 1 1 calc R . . N2 N 0.5536(3) 0.5536(3) 0 0.0681(12) Uani 1 2 d S . . C1 C 0.4563(3) 0.4563(3) 0 0.0419(9) Uani 1 2 d S . . C2 C 0.5543(9) 0.6659(6) 0.0350(2) 0.136(3) Uani 1 1 d . . . H2A H 0.6285 0.6485 0.0591 0.164 Uiso 1 1 calc R . . H2B H 0.5767 0.7535 0.018 0.164 Uiso 1 1 calc R . . C3 C 0.4307(7) 0.6819(7) 0.0591(3) 0.139(3) Uani 1 1 d . . . H3A H 0.3755 0.7495 0.0403 0.167 Uiso 1 1 calc R . . H3B H 0.4526 0.7266 0.0905 0.167 Uiso 1 1 calc R . . C4 C 0.3397(6) 0.5662(4) 0.06978(13) 0.0820(14) Uani 1 1 d . . . H4A H 0.2424 0.5986 0.0706 0.098 Uiso 1 1 calc R . . H4B H 0.3628 0.5275 0.102 0.098 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C5 0.0288(12) 0.0265(11) 0.0262(10) -0.0023(9) -0.0013(9) -0.0039(9) C6 0.0329(13) 0.0340(13) 0.0350(11) 0.0040(11) 0.0033(10) 0.0019(11) C7 0.0474(17) 0.0338(14) 0.0422(13) 0.0128(11) 0.0016(12) 0.0008(13) C8 0.0484(17) 0.0414(15) 0.0406(13) 0.0121(12) 0.0079(13) -0.0096(13) C9 0.0321(14) 0.0522(18) 0.0455(14) 0.0086(13) 0.0084(12) -0.0030(12) C10 0.0318(13) 0.0370(14) 0.0368(12) 0.0079(11) -0.0006(10) 0.0009(11) C11 0.0271(12) 0.0289(12) 0.0297(11) 0.0019(10) 0.0015(9) -0.0024(9) C12 0.063(2) 0.0342(13) 0.0331(12) 0.0005(11) 0.0119(13) -0.0015(14) C13 0.085(3) 0.0355(15) 0.0495(16) -0.0077(13) 0.0289(17) -0.0051(16) C14 0.062(2) 0.0277(13) 0.0572(18) -0.0004(13) 0.0186(16) -0.0026(13) C15 0.0445(15) 0.0304(13) 0.0437(14) 0.0094(11) 0.0062(12) -0.0033(11) C16 0.0362(13) 0.0327(13) 0.0314(11) 0.0003(10) 0.0039(10) -0.0013(11) B 0.0280(11) 0.0280(11) 0.0261(16) 0.0006(10) -0.0006(10) -0.0016(16) N1 0.0561(16) 0.0476(15) 0.0479(12) 0.0006(12) 0.0059(12) -0.0011(12) N2 0.0637(18) 0.0637(18) 0.077(3) 0.0009(17) -0.0009(17) -0.022(2) C1 0.0419(14) 0.0419(14) 0.0418(19) 0.0056(12) -0.0056(12) 0.0021(18) C2 0.183(7) 0.074(3) 0.153(5) -0.035(4) 0.007(5) -0.053(4) C3 0.094(4) 0.121(5) 0.203(7) -0.107(5) 0.001(5) -0.022(4) C4 0.134(4) 0.059(2) 0.0531(18) 0.0010(18) 0.010(2) 0.034(3) #----------------------------------------------------------------------------# # 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 C5 C6 1.394(3) . ? C5 C10 1.404(4) . ? C5 B 1.645(3) . ? C6 C7 1.394(3) . ? C6 H6 0.95 . ? C7 C8 1.375(4) . ? C7 H7 0.95 . ? C8 C9 1.376(4) . ? C8 H8 0.95 . ? C9 C10 1.390(4) . ? C9 H9 0.95 . ? C10 H10 0.95 . ? C11 C12 1.398(3) . ? C11 C16 1.405(3) . ? C11 B 1.643(3) . ? C12 C13 1.399(4) . ? C12 H12 0.95 . ? C13 C14 1.370(4) . ? C13 H13 0.95 . ? C14 C15 1.382(4) . ? C14 H14 0.95 . ? C15 C16 1.390(4) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? N1 C1 1.330(3) . ? N1 C4 1.472(4) . ? N1 H1 0.88 . ? N2 C1 1.327(6) . ? N2 C2 1.452(6) 5 ? N2 C2 1.452(6) . ? C1 N1 1.330(3) 5 ? C2 C3 1.374(9) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.450(7) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.99 . ? C4 H4B 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 C6 C5 C10 115.0(2) . . ? C6 C5 B 124.6(2) . . ? C10 C5 B 120.1(2) . . ? C5 C6 C7 122.6(2) . . ? C5 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 118.8(2) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C8 C9 C10 120.3(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 122.7(2) . . ? C9 C10 H10 118.6 . . ? C5 C10 H10 118.6 . . ? C12 C11 C16 114.7(2) . . ? C12 C11 B 124.60(19) . . ? C16 C11 B 120.59(19) . . ? C11 C12 C13 122.4(2) . . ? C11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 118.8(3) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C14 C15 C16 120.0(2) . . ? C14 C15 H15 120 . . ? C16 C15 H15 120 . . ? C15 C16 C11 123.2(2) . . ? C15 C16 H16 118.4 . . ? C11 C16 H16 118.4 . . ? C11 B C11 105.1(3) . 5_465 ? C11 B C5 112.44(11) . . ? C11 B C5 111.65(12) . 5_465 ? C5 B C5 103.8(3) . 5_465 ? C1 N1 C4 123.5(3) . . ? C1 N1 H1 118.2 . . ? C4 N1 H1 118.2 . . ? C1 N2 C2 122.1(3) . 5 ? C1 N2 C2 122.1(3) . . ? C2 N2 C2 115.8(7) 5 . ? N2 C1 N1 120.8(2) . 5 ? N2 C1 N1 120.84(19) . . ? N1 C1 N1 118.3(4) 5 . ? C3 C2 N2 113.7(5) . . ? C3 C2 H2A 108.8 . . ? N2 C2 H2A 108.8 . . ? C3 C2 H2B 108.8 . . ? N2 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 122.5(5) . . ? C2 C3 H3A 106.7 . . ? C4 C3 H3A 106.7 . . ? C2 C3 H3B 106.7 . . ? C4 C3 H3B 106.7 . . ? H3A C3 H3B 106.6 . . ? C3 C4 N1 110.2(4) . . ? C3 C4 H4A 109.6 . . ? N1 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? N1 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? #===END data_may608 _database_code_depnum_ccdc_archive 'CCDC 693297' _audit_creation_date 2008-05-14T13:56:58-00:00 _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 'C5 H10 N3, Cl' _chemical_formula_sum 'C5 H10 Cl N3' _chemical_formula_weight 147.61 _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 13.5414(5) _cell_length_b 13.5232(5) _cell_length_c 16.1341(5) _cell_angle_alpha 90 _cell_angle_beta 101.462(2) _cell_angle_gamma 90 _cell_volume 2895.60(18) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11145 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.442 _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 0.65211E-1 _diffrn_orient_matrix_ub_12 -0.122747E-1 _diffrn_orient_matrix_ub_13 -0.184232E-1 _diffrn_orient_matrix_ub_21 0.101126E-1 _diffrn_orient_matrix_ub_22 0.729004E-1 _diffrn_orient_matrix_ub_23 -0.45407E-2 _diffrn_orient_matrix_ub_31 0.363721E-1 _diffrn_orient_matrix_ub_32 0.17385E-2 _diffrn_orient_matrix_ub_33 0.603282E-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 0.066 _diffrn_reflns_av_unetI/netI 0.0611 _diffrn_reflns_number 18447 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 26.03 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 5654 _reflns_number_gt 3939 _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 ; H atoms on N 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^)+(0.0392P)^2^+1.7070P] 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 5654 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.101 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.305 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.051 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 Cl1 Cl 0.38697(6) 0.94019(5) 0.34747(5) 0.0497(2) Uani 1 1 d . . . Cl2 Cl 0.51268(6) 0.62072(5) 0.35428(4) 0.0417(2) Uani 1 1 d . . . Cl3 Cl 0.04621(6) 0.09847(5) 0.89544(4) 0.04185(19) Uani 1 1 d . . . Cl4 Cl 0.14030(6) 0.02549(5) 0.62233(5) 0.0461(2) Uani 1 1 d . . . N1 N 0.3844(2) 0.85390(19) 0.5255(2) 0.0488(7) Uani 1 1 d . . . H1X H 0.389(2) 0.880(2) 0.4833(18) 0.038(9) Uiso 1 1 d . . . N2 N 0.3825(2) 0.68133(18) 0.48703(16) 0.0429(6) Uani 1 1 d . . . H2X H 0.408(3) 0.684(3) 0.445(2) 0.081(14) Uiso 1 1 d . . . N3 N 0.37239(19) 0.7325(2) 0.61482(14) 0.0479(6) Uani 1 1 d . . . N4 N 0.6123(2) 0.7564(2) 0.23861(16) 0.0452(6) Uani 1 1 d . . . H4X H 0.587(3) 0.717(3) 0.267(2) 0.065(11) Uiso 1 1 d . . . N5 N 0.6322(2) 0.6645(2) 0.11438(17) 0.0445(7) Uani 1 1 d . . . H5X H 0.625(2) 0.614(2) 0.1278(18) 0.036(9) Uiso 1 1 d . . . N6 N 0.63182(17) 0.82756(16) 0.11924(14) 0.0356(5) Uani 1 1 d . . . N7 N -0.0686(2) 0.2055(2) 1.02044(18) 0.0510(7) Uani 1 1 d . . . H7X H -0.050(3) 0.165(3) 0.995(2) 0.055(11) Uiso 1 1 d . . . N8 N -0.1321(2) 0.11433(19) 1.12767(17) 0.0466(7) Uani 1 1 d . . . H8X H -0.118(2) 0.060(2) 1.1206(18) 0.044(9) Uiso 1 1 d . . . N9 N -0.15297(18) 0.27437(16) 1.10774(14) 0.0391(6) Uani 1 1 d . . . N10 N 0.0851(2) 0.2935(2) 0.79665(17) 0.0443(7) Uani 1 1 d . . . H10X H 0.075(2) 0.246(2) 0.8127(17) 0.029(9) Uiso 1 1 d . . . N11 N 0.1390(2) 0.24443(19) 0.66817(16) 0.0476(7) Uani 1 1 d . . . H11X H 0.139(2) 0.183(3) 0.666(2) 0.055(10) Uiso 1 1 d . . . N12 N 0.1558(2) 0.39427(16) 0.71935(15) 0.0474(7) Uani 1 1 d . . . C1 C 0.38164(19) 0.7588(2) 0.53646(16) 0.0335(6) Uani 1 1 d . . . C2 C 0.3721(2) 0.9024(3) 0.6053(3) 0.0685(11) Uani 1 1 d . . . H2A H 0.3211 0.9557 0.5942 0.082 Uiso 1 1 calc R . . H2B H 0.4367 0.9305 0.6357 0.082 Uiso 1 1 calc R . . C3 C 0.3376(3) 0.8191(3) 0.6549(2) 0.0654(11) Uani 1 1 d . . . H3A H 0.3694 0.823 0.7156 0.079 Uiso 1 1 calc R . . H3B H 0.2634 0.8189 0.6489 0.079 Uiso 1 1 calc R . . C4 C 0.3391(3) 0.6309(3) 0.6121(2) 0.0633(10) Uani 1 1 d . . . H4A H 0.2648 0.6263 0.6031 0.076 Uiso 1 1 calc R . . H4B H 0.3693 0.5951 0.6646 0.076 Uiso 1 1 calc R . . C5 C 0.3779(3) 0.5920(2) 0.5370(2) 0.0617(10) Uani 1 1 d . . . H5A H 0.4454 0.5617 0.5546 0.074 Uiso 1 1 calc R . . H5B H 0.3311 0.5428 0.5051 0.074 Uiso 1 1 calc R . . C6 C 0.62234(19) 0.7426(2) 0.16043(17) 0.0352(6) Uani 1 1 d . . . C7 C 0.6114(3) 0.8637(2) 0.25460(19) 0.0527(8) Uani 1 1 d . . . H7A H 0.6529 0.8805 0.3105 0.063 Uiso 1 1 calc R . . H7B H 0.5419 0.8883 0.2517 0.063 Uiso 1 1 calc R . . C8 C 0.6571(2) 0.9060(2) 0.18274(18) 0.0442(7) Uani 1 1 d . . . H8A H 0.6256 0.9697 0.162 0.053 Uiso 1 1 calc R . . H8B H 0.7309 0.915 0.2001 0.053 Uiso 1 1 calc R . . C9 C 0.6796(2) 0.8050(2) 0.04748(18) 0.0424(7) Uani 1 1 d . . . H9A H 0.7538 0.8121 0.0627 0.051 Uiso 1 1 calc R . . H9B H 0.653 0.8472 -0.002 0.051 Uiso 1 1 calc R . . C10 C 0.6482(2) 0.6964(2) 0.03111(19) 0.0465(7) Uani 1 1 d . . . H10A H 0.5855 0.6908 -0.0123 0.056 Uiso 1 1 calc R . . H10B H 0.702 0.6574 0.013 0.056 Uiso 1 1 calc R . . C11 C -0.1151(2) 0.19131(19) 1.08302(17) 0.0339(6) Uani 1 1 d . . . C12 C -0.0663(2) 0.3110(2) 1.00096(19) 0.0449(7) Uani 1 1 d . . . H12A H -0.1079 0.3256 0.9446 0.054 Uiso 1 1 calc R . . H12B H 0.0034 0.3339 1.0026 0.054 Uiso 1 1 calc R . . C13 C -0.1108(2) 0.3592(2) 1.07137(19) 0.0413(7) Uani 1 1 d . . . H13A H -0.0579 0.3921 1.1136 0.05 Uiso 1 1 calc R . . H13B H -0.1636 0.408 1.0482 0.05 Uiso 1 1 calc R . . C14 C -0.1797(2) 0.2588(2) 1.19035(18) 0.0416(7) Uani 1 1 d . . . H14A H -0.2443 0.2912 1.1938 0.05 Uiso 1 1 calc R . . H14B H -0.1262 0.283 1.2369 0.05 Uiso 1 1 calc R . . C15 C -0.1887(2) 0.1454(2) 1.19169(19) 0.0474(8) Uani 1 1 d . . . H15A H -0.1584 0.1183 1.248 0.057 Uiso 1 1 calc R . . H15B H -0.26 0.1241 1.1764 0.057 Uiso 1 1 calc R . . C16 C 0.12529(19) 0.30286(18) 0.72921(16) 0.0317(6) Uani 1 1 d . . . C17 C 0.0905(3) 0.3883(2) 0.8415(2) 0.0533(8) Uani 1 1 d . . . H17A H 0.1398 0.3853 0.8957 0.064 Uiso 1 1 calc R . . H17B H 0.0238 0.4073 0.8528 0.064 Uiso 1 1 calc R . . C18 C 0.1250(2) 0.4608(2) 0.78001(18) 0.0436(7) Uani 1 1 d . . . H18A H 0.0691 0.5042 0.7527 0.052 Uiso 1 1 calc R . . H18B H 0.1819 0.502 0.8089 0.052 Uiso 1 1 calc R . . C19 C 0.1859(3) 0.4068(2) 0.63990(19) 0.0485(8) Uani 1 1 d . . . H19A H 0.2533 0.4379 0.6471 0.058 Uiso 1 1 calc R . . H19B H 0.1365 0.4472 0.6005 0.058 Uiso 1 1 calc R . . C20 C 0.1877(2) 0.2994(2) 0.60916(18) 0.0445(7) Uani 1 1 d . . . H20A H 0.1497 0.2925 0.5504 0.053 Uiso 1 1 calc R . . H20B H 0.2577 0.2763 0.6121 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0563(5) 0.0336(4) 0.0638(5) -0.0062(3) 0.0231(4) -0.0069(3) Cl2 0.0581(5) 0.0344(4) 0.0337(3) 0.0023(3) 0.0121(3) -0.0035(3) Cl3 0.0596(5) 0.0255(3) 0.0462(4) -0.0049(3) 0.0243(3) 0.0001(3) Cl4 0.0428(4) 0.0306(4) 0.0630(5) -0.0086(3) 0.0062(3) 0.0060(3) N1 0.0501(17) 0.0362(15) 0.0596(18) 0.0036(14) 0.0094(14) 0.0005(12) N2 0.0541(17) 0.0378(14) 0.0361(14) -0.0010(12) 0.0074(12) 0.0069(12) N3 0.0515(16) 0.0598(17) 0.0339(13) -0.0061(12) 0.0122(11) -0.0106(13) N4 0.0496(16) 0.0488(16) 0.0374(14) 0.0065(12) 0.0089(12) -0.0123(13) N5 0.0532(17) 0.0287(14) 0.0492(16) 0.0055(13) 0.0045(12) -0.0072(12) N6 0.0364(13) 0.0327(12) 0.0387(12) 0.0054(10) 0.0101(10) -0.0001(10) N7 0.0629(19) 0.0373(15) 0.0626(18) -0.0098(14) 0.0362(15) -0.0014(13) N8 0.0581(18) 0.0235(13) 0.0643(17) 0.0053(12) 0.0271(14) 0.0097(12) N9 0.0501(15) 0.0271(12) 0.0457(13) 0.0025(10) 0.0228(11) 0.0046(11) N10 0.0528(17) 0.0352(15) 0.0485(16) 0.0097(13) 0.0191(13) -0.0024(13) N11 0.073(2) 0.0255(14) 0.0490(15) -0.0015(12) 0.0240(13) -0.0037(13) N12 0.0760(19) 0.0241(12) 0.0498(15) -0.0029(11) 0.0310(13) -0.0054(12) C1 0.0324(15) 0.0337(16) 0.0343(15) -0.0003(12) 0.0067(11) -0.0009(12) C2 0.0374(19) 0.058(2) 0.110(3) -0.048(2) 0.0143(19) -0.0018(16) C3 0.042(2) 0.106(3) 0.0492(19) -0.036(2) 0.0118(15) -0.006(2) C4 0.058(2) 0.070(2) 0.056(2) 0.0253(19) -0.0039(17) -0.0216(19) C5 0.076(3) 0.0359(17) 0.064(2) 0.0071(16) -0.0092(18) -0.0029(17) C6 0.0285(15) 0.0368(16) 0.0378(16) 0.0091(13) 0.0005(12) -0.0047(12) C7 0.0484(19) 0.064(2) 0.0452(17) -0.0066(16) 0.0085(15) 0.0055(16) C8 0.0477(18) 0.0308(15) 0.0513(18) 0.0016(13) 0.0026(14) 0.0018(13) C9 0.0417(17) 0.0445(17) 0.0429(16) 0.0096(13) 0.0130(13) -0.0018(14) C10 0.0469(19) 0.0476(18) 0.0466(17) -0.0004(14) 0.0131(14) 0.0042(15) C11 0.0330(15) 0.0282(14) 0.0413(15) -0.0060(12) 0.0095(12) 0.0024(12) C12 0.0473(19) 0.0430(17) 0.0471(17) 0.0025(14) 0.0158(14) -0.0049(14) C13 0.0412(17) 0.0286(15) 0.0556(18) 0.0024(13) 0.0132(14) -0.0014(12) C14 0.0446(18) 0.0384(16) 0.0461(17) 0.0030(13) 0.0193(14) 0.0125(14) C15 0.056(2) 0.0399(17) 0.0514(18) 0.0104(14) 0.0227(15) 0.0077(15) C16 0.0326(15) 0.0260(13) 0.0362(14) 0.0040(12) 0.0060(12) 0.0017(11) C17 0.067(2) 0.0499(19) 0.0488(18) 0.0017(15) 0.0242(16) 0.0131(17) C18 0.0503(18) 0.0332(15) 0.0477(17) -0.0050(13) 0.0104(14) 0.0072(13) C19 0.059(2) 0.0375(16) 0.0543(18) 0.0086(14) 0.0248(16) -0.0052(15) C20 0.0514(19) 0.0459(17) 0.0387(15) 0.0002(14) 0.0146(14) 0.0041(15) #----------------------------------------------------------------------------# # 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 1.300(4) . ? N1 C2 1.483(4) . ? N1 H1X 0.78(3) . ? N2 C1 1.318(4) . ? N2 C5 1.460(4) . ? N2 H2X 0.83(4) . ? N3 C1 1.343(3) . ? N3 C4 1.445(4) . ? N3 C3 1.460(4) . ? N4 C6 1.309(4) . ? N4 C7 1.474(4) . ? N4 H4X 0.82(4) . ? N5 C6 1.314(4) . ? N5 C10 1.467(4) . ? N5 H5X 0.73(3) . ? N6 C6 1.346(3) . ? N6 C9 1.467(4) . ? N6 C8 1.467(4) . ? N7 C11 1.306(4) . ? N7 C12 1.463(4) . ? N7 H7X 0.75(3) . ? N8 C11 1.312(4) . ? N8 C15 1.464(4) . ? N8 H8X 0.78(3) . ? N9 C11 1.329(3) . ? N9 C13 1.456(3) . ? N9 C14 1.464(3) . ? N10 C16 1.316(4) . ? N10 C17 1.466(4) . ? N10 H10X 0.71(3) . ? N11 C16 1.305(4) . ? N11 C20 1.464(4) . ? N11 H11X 0.83(3) . ? N12 C16 1.323(3) . ? N12 C19 1.430(4) . ? N12 C18 1.450(3) . ? C2 C3 1.509(5) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.509(5) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C7 C8 1.530(4) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.537(4) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C12 C13 1.533(4) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.539(4) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C17 C18 1.532(4) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 C20 1.537(4) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 H20A 0.99 . ? C20 H20B 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 108.0(3) . . ? C1 N1 H1X 125(2) . . ? C2 N1 H1X 127(2) . . ? C1 N2 C5 108.5(2) . . ? C1 N2 H2X 121(3) . . ? C5 N2 H2X 124(3) . . ? C1 N3 C4 108.1(2) . . ? C1 N3 C3 107.7(3) . . ? C4 N3 C3 130.5(3) . . ? C6 N4 C7 108.4(2) . . ? C6 N4 H4X 125(3) . . ? C7 N4 H4X 122(3) . . ? C6 N5 C10 109.3(2) . . ? C6 N5 H5X 123(2) . . ? C10 N5 H5X 127(2) . . ? C6 N6 C9 108.2(2) . . ? C6 N6 C8 107.7(2) . . ? C9 N6 C8 128.6(2) . . ? C11 N7 C12 110.0(2) . . ? C11 N7 H7X 125(3) . . ? C12 N7 H7X 124(3) . . ? C11 N8 C15 109.5(2) . . ? C11 N8 H8X 126(2) . . ? C15 N8 H8X 124(2) . . ? C11 N9 C13 109.8(2) . . ? C11 N9 C14 109.4(2) . . ? C13 N9 C14 131.9(2) . . ? C16 N10 C17 109.6(2) . . ? C16 N10 H10X 122(2) . . ? C17 N10 H10X 127(2) . . ? C16 N11 C20 109.5(2) . . ? C16 N11 H11X 129(2) . . ? C20 N11 H11X 119(2) . . ? C16 N12 C19 111.7(2) . . ? C16 N12 C18 111.0(2) . . ? C19 N12 C18 134.6(2) . . ? N1 C1 N2 134.5(3) . . ? N1 C1 N3 113.6(3) . . ? N2 C1 N3 111.9(2) . . ? N1 C2 C3 103.3(3) . . ? N1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? N1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109.1 . . ? N3 C3 C2 101.6(2) . . ? N3 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? N3 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.3 . . ? N3 C4 C5 101.5(3) . . ? N3 C4 H4A 111.5 . . ? C5 C4 H4A 111.5 . . ? N3 C4 H4B 111.5 . . ? C5 C4 H4B 111.5 . . ? H4A C4 H4B 109.3 . . ? N2 C5 C4 102.4(3) . . ? N2 C5 H5A 111.3 . . ? C4 C5 H5A 111.3 . . ? N2 C5 H5B 111.3 . . ? C4 C5 H5B 111.3 . . ? H5A C5 H5B 109.2 . . ? N4 C6 N5 134.6(3) . . ? N4 C6 N6 113.1(3) . . ? N5 C6 N6 112.1(2) . . ? N4 C7 C8 102.5(2) . . ? N4 C7 H7A 111.3 . . ? C8 C7 H7A 111.3 . . ? N4 C7 H7B 111.3 . . ? C8 C7 H7B 111.3 . . ? H7A C7 H7B 109.2 . . ? N6 C8 C7 100.7(2) . . ? N6 C8 H8A 111.6 . . ? C7 C8 H8A 111.6 . . ? N6 C8 H8B 111.6 . . ? C7 C8 H8B 111.6 . . ? H8A C8 H8B 109.4 . . ? N6 C9 C10 100.6(2) . . ? N6 C9 H9A 111.7 . . ? C10 C9 H9A 111.7 . . ? N6 C9 H9B 111.7 . . ? C10 C9 H9B 111.7 . . ? H9A C9 H9B 109.4 . . ? N5 C10 C9 102.1(2) . . ? N5 C10 H10A 111.3 . . ? C9 C10 H10A 111.3 . . ? N5 C10 H10B 111.3 . . ? C9 C10 H10B 111.3 . . ? H10A C10 H10B 109.2 . . ? N7 C11 N8 134.8(3) . . ? N7 C11 N9 112.5(2) . . ? N8 C11 N9 112.7(2) . . ? N7 C12 C13 103.2(2) . . ? N7 C12 H12A 111.1 . . ? C13 C12 H12A 111.1 . . ? N7 C12 H12B 111.1 . . ? C13 C12 H12B 111.1 . . ? H12A C12 H12B 109.1 . . ? N9 C13 C12 101.9(2) . . ? N9 C13 H13A 111.4 . . ? C12 C13 H13A 111.4 . . ? N9 C13 H13B 111.4 . . ? C12 C13 H13B 111.4 . . ? H13A C13 H13B 109.2 . . ? N9 C14 C15 101.0(2) . . ? N9 C14 H14A 111.6 . . ? C15 C14 H14A 111.6 . . ? N9 C14 H14B 111.6 . . ? C15 C14 H14B 111.6 . . ? H14A C14 H14B 109.4 . . ? N8 C15 C14 102.8(2) . . ? N8 C15 H15A 111.2 . . ? C14 C15 H15A 111.2 . . ? N8 C15 H15B 111.2 . . ? C14 C15 H15B 111.2 . . ? H15A C15 H15B 109.1 . . ? N11 C16 N10 135.3(3) . . ? N11 C16 N12 112.3(2) . . ? N10 C16 N12 112.3(2) . . ? N10 C17 C18 103.4(2) . . ? N10 C17 H17A 111.1 . . ? C18 C17 H17A 111.1 . . ? N10 C17 H17B 111.1 . . ? C18 C17 H17B 111.1 . . ? H17A C17 H17B 109 . . ? N12 C18 C17 101.9(2) . . ? N12 C18 H18A 111.4 . . ? C17 C18 H18A 111.4 . . ? N12 C18 H18B 111.4 . . ? C17 C18 H18B 111.4 . . ? H18A C18 H18B 109.3 . . ? N12 C19 C20 101.7(2) . . ? N12 C19 H19A 111.4 . . ? C20 C19 H19A 111.4 . . ? N12 C19 H19B 111.4 . . ? C20 C19 H19B 111.4 . . ? H19A C19 H19B 109.3 . . ? N11 C20 C19 103.4(2) . . ? N11 C20 H20A 111.1 . . ? C19 C20 H20A 111.1 . . ? N11 C20 H20B 111.1 . . ? C19 C20 H20B 111.1 . . ? H20A C20 H20B 109 . . ? #===END