# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_c2c _database_code_depnum_ccdc_archive 'CCDC 878735' _audit_creation_date 2012-04-19T13:00:11-00:00 _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 ; 3-[(1H-indol-3-yl)(phenyl)methylene]-3H-indole ; _chemical_name_common 3-[(1H-indol-3-yl)(phenyl)methylene]-3H-indol _chemical_formula_moiety 'C23 H21 Cl N2 O2' _chemical_formula_sum 'C23 H21 Cl N2 O2' _chemical_formula_weight 392.87 _chemical_melting_point none #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc 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 11.9856(3) _cell_length_b 18.2571(3) _cell_length_c 9.0361(2) _cell_angle_alpha 90 _cell_angle_beta 94.4630(10) _cell_angle_gamma 90 _cell_volume 1971.30(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5705 _cell_measurement_theta_min 2.9435 _cell_measurement_theta_max 27.6345 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description tabular _exptl_crystal_colour red _exptl_crystal_size_max 0.332 _exptl_crystal_size_mid 0.198 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_special_details ; XPREP (Bruker, 2006) was used to perform the Gaussian absorption correction based on the face-indexed crystal size ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details XPREP _exptl_absorpt_correction_T_min 0.6999 _exptl_absorpt_correction_T_max 0.7456 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean none _diffrn_measurement_device_type 'X8 APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_unetI/netI 0.013 _diffrn_reflns_number 16042 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.87 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 2343 _reflns_number_gt 1910 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'BRUKER APEX-II' _computing_cell_refinement 'BRUKER SANT' _computing_data_reduction 'BRUKER SOFTWARE' _computing_structure_solution 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0978P)^2^+1.0610P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 2343 _refine_ls_number_parameters 129 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.157 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.288 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 Cl Cl 0.5 0.51135(4) 0.75 0.0900(4) Uani 1 2 d S . . N N 0.55059(14) 0.65065(8) 0.55373(18) 0.0484(4) Uani 1 1 d . . . H0 H 0.5452 0.6087 0.5958 0.058 Uiso 1 1 calc R . . C11 C 0.5 0.85746(11) 0.25 0.0349(5) Uani 1 2 d S . . C8 C 0.60748(14) 0.71050(10) 0.61730(19) 0.0433(4) Uani 1 1 d . . . C3 C 0.59734(13) 0.76829(9) 0.51524(17) 0.0369(4) Uani 1 1 d . . . C4 C 0.65154(15) 0.83450(10) 0.5529(2) 0.0431(4) Uani 1 1 d . . . H4 H 0.6489 0.8734 0.4862 0.052 Uiso 1 1 calc R . . C12 C 0.56700(15) 0.89591(10) 0.1577(2) 0.0435(4) Uani 1 1 d . . . H12 H 0.6107 0.8708 0.0938 0.052 Uiso 1 1 calc R . . C2 C 0.53209(13) 0.74023(8) 0.38444(17) 0.0369(4) Uani 1 1 d . . . C1 C 0.50572(16) 0.66729(9) 0.4189(2) 0.0440(4) Uani 1 1 d . . . H1 H 0.4633 0.6356 0.3567 0.053 Uiso 1 1 calc R . . C6 C 0.71528(17) 0.78259(14) 0.7919(2) 0.0581(5) Uani 1 1 d . . . H6 H 0.7534 0.7889 0.8847 0.07 Uiso 1 1 calc R . . C5 C 0.70887(17) 0.84092(12) 0.6909(2) 0.0534(5) Uani 1 1 d . . . H5 H 0.744 0.8849 0.7174 0.064 Uiso 1 1 calc R . . C13 C 0.56828(18) 0.97143(11) 0.1611(3) 0.0558(5) Uani 1 1 d . . . H13 H 0.6156 0.9972 0.103 0.067 Uiso 1 1 calc R . . C14 C 0.5 1.00871(15) 0.25 0.0619(8) Uani 1 2 d S . . H14 H 0.5 1.0597 0.25 0.074 Uiso 1 2 calc SR . . C7 C 0.66612(16) 0.71609(13) 0.7562(2) 0.0550(5) Uani 1 1 d . . . H7 H 0.6718 0.6767 0.8217 0.066 Uiso 1 1 calc R . . O O 0.6938(3) 0.5341(3) 1.0187(4) 0.1695(15) Uani 1 1 d . . . C10 C 0.5 0.77627(12) 0.25 0.0348(5) Uani 1 2 d S . . H1C H 0.637 0.5174 0.9135 0.05 Uiso 1 1 d D . . H1D H 0.6443 0.5174 1.1229 0.05 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl 0.1927(12) 0.0310(4) 0.0495(5) 0 0.0297(5) 0 N 0.0621(9) 0.0353(8) 0.0484(8) 0.0136(6) 0.0085(7) 0.0028(6) C11 0.0426(11) 0.0272(10) 0.0337(10) 0 -0.0041(8) 0 C8 0.0461(9) 0.0446(9) 0.0400(9) 0.0075(7) 0.0072(7) 0.0076(7) C3 0.0429(8) 0.0338(8) 0.0341(8) 0.0008(6) 0.0036(6) 0.0065(6) C4 0.0500(9) 0.0364(9) 0.0422(9) -0.0027(7) -0.0018(7) 0.0043(7) C12 0.0509(9) 0.0348(9) 0.0445(9) 0.0037(7) 0.0017(7) -0.0022(7) C2 0.0477(8) 0.0268(7) 0.0362(8) 0.0003(6) 0.0038(6) 0.0011(6) C1 0.0576(10) 0.0309(8) 0.0439(9) 0.0025(7) 0.0069(7) 0.0001(7) C6 0.0523(10) 0.0824(16) 0.0384(9) 0.0003(9) -0.0041(7) 0.0056(10) C5 0.0534(10) 0.0558(11) 0.0494(10) -0.0103(8) -0.0056(8) 0.0046(8) C13 0.0669(12) 0.0354(9) 0.0644(12) 0.0106(8) 0.0005(9) -0.0089(8) C14 0.080(2) 0.0265(12) 0.078(2) 0 -0.0031(16) 0 C7 0.0530(10) 0.0725(14) 0.0393(9) 0.0173(9) 0.0030(7) 0.0109(9) O 0.124(2) 0.221(4) 0.167(3) -0.036(3) 0.031(2) -0.025(3) C10 0.0417(10) 0.0274(10) 0.0351(10) 0 0.0026(8) 0 #----------------------------------------------------------------------------# # 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 N C1 1.328(2) . ? N C8 1.389(3) . ? N H0 0.86 . ? C11 C12 1.392(2) . ? C11 C12 1.392(2) 2_655 ? C11 C10 1.482(3) . ? C8 C7 1.394(3) . ? C8 C3 1.400(2) . ? C3 C4 1.402(2) . ? C3 C2 1.459(2) . ? C4 C5 1.381(2) . ? C4 H4 0.93 . ? C12 C13 1.379(3) . ? C12 H12 0.93 . ? C2 C10 1.4086(18) . ? C2 C1 1.409(2) . ? C1 H1 0.93 . ? C6 C7 1.377(3) . ? C6 C5 1.401(3) . ? C6 H6 0.93 . ? C5 H5 0.93 . ? C13 C14 1.371(3) . ? C13 H13 0.93 . ? C14 C13 1.371(3) 2_655 ? C14 H14 0.93 . ? C7 H7 0.93 . ? O H1C 1.166(4) . ? O H1D 1.191(4) . ? C10 C2 1.4086(18) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N C8 110.50(15) . . ? C1 N H0 124.8 . . ? C8 N H0 124.8 . . ? C12 C11 C12 119.4(2) . 2_655 ? C12 C11 C10 120.28(11) . . ? C12 C11 C10 120.28(11) 2_655 . ? N C8 C7 128.84(17) . . ? N C8 C3 107.81(15) . . ? C7 C8 C3 123.35(18) . . ? C8 C3 C4 118.37(15) . . ? C8 C3 C2 106.41(15) . . ? C4 C3 C2 135.14(15) . . ? C5 C4 C3 118.74(17) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C13 C12 C11 119.76(18) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C10 C2 C1 125.56(15) . . ? C10 C2 C3 128.90(15) . . ? C1 C2 C3 105.55(14) . . ? N C1 C2 109.72(15) . . ? N C1 H1 125.1 . . ? C2 C1 H1 125.1 . . ? C7 C6 C5 121.11(17) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C4 C5 C6 121.48(19) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C13 120.5(3) 2_655 . ? C13 C14 H14 119.8 2_655 . ? C13 C14 H14 119.8 . . ? C6 C7 C8 116.90(18) . . ? C6 C7 H7 121.6 . . ? C8 C7 H7 121.6 . . ? H1C O H1D 106.4(3) . . ? C2 C10 C2 124.3(2) 2_655 . ? C2 C10 C11 117.85(10) 2_655 . ? C2 C10 C11 117.85(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N C8 C7 -179.78(19) . . . . ? C1 N C8 C3 0.0(2) . . . . ? N C8 C3 C4 -177.94(15) . . . . ? C7 C8 C3 C4 1.9(3) . . . . ? N C8 C3 C2 -0.69(19) . . . . ? C7 C8 C3 C2 179.11(17) . . . . ? C8 C3 C4 C5 -2.5(3) . . . . ? C2 C3 C4 C5 -178.72(18) . . . . ? C12 C11 C12 C13 1.51(13) 2_655 . . . ? C10 C11 C12 C13 -178.49(13) . . . . ? C8 C3 C2 C10 -179.03(15) . . . . ? C4 C3 C2 C10 -2.5(3) . . . . ? C8 C3 C2 C1 1.09(18) . . . . ? C4 C3 C2 C1 177.65(19) . . . . ? C8 N C1 C2 0.7(2) . . . . ? C10 C2 C1 N 178.99(15) . . . . ? C3 C2 C1 N -1.1(2) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C7 C6 C5 C4 1.1(3) . . . . ? C11 C12 C13 C14 -3.0(3) . . . . ? C12 C13 C14 C13 1.53(13) . . . 2_655 ? C5 C6 C7 C8 -1.8(3) . . . . ? N C8 C7 C6 -179.98(18) . . . . ? C3 C8 C7 C6 0.3(3) . . . . ? C1 C2 C10 C2 -20.60(14) . . . 2_655 ? C3 C2 C10 C2 159.54(19) . . . 2_655 ? C1 C2 C10 C11 159.40(14) . . . . ? C3 C2 C10 C11 -20.46(19) . . . . ? C12 C11 C10 C2 -59.68(11) . . . 2_655 ? C12 C11 C10 C2 120.32(11) 2_655 . . 2_655 ? C12 C11 C10 C2 120.32(11) . . . . ? C12 C11 C10 C2 -59.68(11) 2_655 . . . ? data_teste2 _database_code_depnum_ccdc_archive 'CCDC 878736' _audit_creation_date 2012-04-19T12:23:06-00:00 _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 ; Tetra(indolyl)dimethane derivative 2 DMSO ; _chemical_name_common 'Tetra(indolyl)dimethane derivative' _chemical_formula_moiety 'C28 H30 N2 O2 S2' _chemical_formula_sum 'C28 H30 N2 O2 S2' _chemical_formula_weight 490.66 _chemical_melting_point none #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.7040(5) _cell_length_b 12.3263(3) _cell_length_c 21.8634(5) _cell_angle_alpha 90 _cell_angle_beta 113.4630(10) _cell_angle_gamma 90 _cell_volume 5118.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7340 _cell_measurement_theta_min 2.504 _cell_measurement_theta_max 26.64 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_special_details ; XPREP (Bruker, 2006) was used to perform the Gaussian absorption correction based on the face-indexed crystal size ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details XPREP _exptl_absorpt_correction_T_min 0.9262 _exptl_absorpt_correction_T_max 0.9588 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean none _diffrn_measurement_device_type 'X8 APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_number 28314 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.15 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 5637 _reflns_number_gt 4421 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'BRUKER APEX-II' _computing_cell_refinement 'BRUKER SANT' _computing_data_reduction 'BRUKER SOFTWARE' _computing_structure_solution 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+7.0671P] 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_extinction_coef none _refine_ls_number_reflns 5637 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1466 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.542 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.061 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 S2 S 0.19490(3) 0.74766(5) 0.06371(3) 0.03579(17) Uani 1 1 d . . . S1 S 0.09927(4) 0.04105(5) 0.95111(3) 0.03793(18) Uani 1 1 d . . . N1 N 0.10091(9) 0.82258(13) 0.81333(8) 0.0205(4) Uani 1 1 d . . . H01 H 0.1122 0.8481 0.8539 0.025 Uiso 1 1 calc R . . O2 O 0.21594(9) 0.85977(14) 0.09296(10) 0.0417(4) Uani 1 1 d . . . O1 O 0.13860(11) -0.03070(15) 0.92262(9) 0.0478(5) Uani 1 1 d . . . C17 C 0.05244(10) 0.60447(14) 0.68509(9) 0.0160(4) Uani 1 1 d . . . C8 C 0.08302(10) 0.71621(14) 0.79360(9) 0.0174(4) Uani 1 1 d . . . N2 N 0.14392(9) 0.60276(13) 0.89251(8) 0.0215(4) Uani 1 1 d . . . H02 H 0.1861 0.6256 0.8978 0.026 Uiso 1 1 calc R . . C28 C 0.10225(15) 0.7515(2) 0.02030(15) 0.0462(7) Uani 1 1 d . . . H28A H 0.09 0.7956 -0.0201 0.069 Uiso 1 1 calc R . . H28B H 0.0811 0.7833 0.049 0.069 Uiso 1 1 calc R . . H28C H 0.0844 0.6776 0.0079 0.069 Uiso 1 1 calc R . . C24 C 0.22989(13) 0.23778(19) 0.82498(14) 0.0382(6) Uani 1 1 d . . . H24A H 0.2791 0.2617 0.8437 0.057 Uiso 1 1 calc R . . H24B H 0.2241 0.1782 0.7935 0.057 Uiso 1 1 calc R . . H24C H 0.2168 0.2128 0.8611 0.057 Uiso 1 1 calc R . . C21 C 0.18307(11) 0.33115(16) 0.78906(10) 0.0242(4) Uani 1 1 d . . . C22 C 0.11040(11) 0.31965(16) 0.75788(10) 0.0225(4) Uani 1 1 d . . . H22 H 0.0896 0.2516 0.7596 0.027 Uiso 1 1 calc R . . C23 C 0.06747(10) 0.40597(15) 0.72421(9) 0.0184(4) Uani 1 1 d . . . H23 H 0.018 0.3957 0.7026 0.022 Uiso 1 1 calc R . . C18 C 0.09637(10) 0.50672(14) 0.72207(9) 0.0166(4) Uani 1 1 d . . . C15 C 0.02566(10) 0.58447(14) 0.85016(9) 0.0159(4) Uani 1 1 d . . . C16 C 0.08122(10) 0.63509(14) 0.84233(9) 0.0175(4) Uani 1 1 d . . . C7 C 0.07056(10) 0.70527(14) 0.72752(9) 0.0161(4) Uani 1 1 d . . . C19 C 0.16909(11) 0.51789(16) 0.75346(11) 0.0244(4) Uani 1 1 d . . . H19 H 0.19 0.5861 0.7523 0.029 Uiso 1 1 calc R . . C20 C 0.21167(11) 0.43207(17) 0.78632(11) 0.0269(5) Uani 1 1 d . . . H20 H 0.2612 0.4422 0.8073 0.032 Uiso 1 1 calc R . . C14 C 0.05643(10) 0.51573(14) 0.90793(9) 0.0172(4) Uani 1 1 d . . . C9 C 0.12987(11) 0.52954(15) 0.93257(10) 0.0207(4) Uani 1 1 d . . . C10 C 0.17572(12) 0.47957(18) 0.99134(11) 0.0285(5) Uani 1 1 d . . . H10 H 0.2252 0.4908 1.0081 0.034 Uiso 1 1 calc R . . C11 C 0.14574(13) 0.41333(19) 1.02370(11) 0.0323(5) Uani 1 1 d . . . H11 H 0.1753 0.3779 1.0637 0.039 Uiso 1 1 calc R . . C12 C 0.07298(13) 0.39685(17) 0.99931(11) 0.0290(5) Uani 1 1 d . . . H12 H 0.0543 0.35 1.0227 0.035 Uiso 1 1 calc R . . C13 C 0.02774(11) 0.44749(15) 0.94174(10) 0.0222(4) Uani 1 1 d . . . H13 H -0.0217 0.4362 0.9255 0.027 Uiso 1 1 calc R . . C1 C 0.09808(10) 0.88185(15) 0.75908(10) 0.0192(4) Uani 1 1 d . . . C6 C 0.07895(10) 0.81088(14) 0.70429(9) 0.0170(4) Uani 1 1 d . . . C5 C 0.07200(11) 0.85238(16) 0.64218(10) 0.0213(4) Uani 1 1 d . . . H5 H 0.0582 0.8065 0.6042 0.026 Uiso 1 1 calc R . . C4 C 0.08561(12) 0.96112(16) 0.63711(11) 0.0267(5) Uani 1 1 d . . . H4 H 0.0811 0.9898 0.5953 0.032 Uiso 1 1 calc R . . C3 C 0.10594(12) 1.02977(16) 0.69280(12) 0.0294(5) Uani 1 1 d . . . H3 H 0.1157 1.1039 0.6882 0.035 Uiso 1 1 calc R . . C2 C 0.11204(12) 0.99165(16) 0.75416(11) 0.0265(5) Uani 1 1 d . . . H2 H 0.1253 1.0384 0.7917 0.032 Uiso 1 1 calc R . . C27 C 0.19970(18) 0.6646(2) 0.13165(15) 0.0536(7) Uani 1 1 d . . . H27A H 0.2491 0.6541 0.1617 0.08 Uiso 1 1 calc R . . H27B H 0.1781 0.594 0.1148 0.08 Uiso 1 1 calc R . . H27C H 0.1745 0.6997 0.1559 0.08 Uiso 1 1 calc R . . C26 C 0.16360(14) 0.1125(2) 1.01808(13) 0.0399(6) Uani 1 1 d . . . H26A H 0.1874 0.0624 1.055 0.06 Uiso 1 1 calc R . . H26B H 0.1408 0.1703 1.0331 0.06 Uiso 1 1 calc R . . H26C H 0.1982 0.1444 1.0032 0.06 Uiso 1 1 calc R . . C25 C 0.06747(17) 0.1521(3) 0.89464(15) 0.0532(7) Uani 1 1 d . . . H25A H 0.0301 0.1267 0.8532 0.08 Uiso 1 1 calc R . . H25B H 0.1061 0.1823 0.8849 0.08 Uiso 1 1 calc R . . H25C H 0.0487 0.2082 0.9148 0.08 Uiso 1 1 calc R . . H17A H 0.0674(12) 0.6195(18) 0.6477(11) 0.020(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S2 0.0342(3) 0.0387(3) 0.0399(4) -0.0087(3) 0.0205(3) -0.0095(2) S1 0.0396(4) 0.0402(3) 0.0355(3) -0.0121(2) 0.0166(3) -0.0097(3) N1 0.0276(9) 0.0161(7) 0.0167(8) -0.0047(6) 0.0078(7) -0.0063(6) O2 0.0317(9) 0.0376(9) 0.0533(11) -0.0121(8) 0.0142(8) -0.0145(7) O1 0.0585(13) 0.0426(10) 0.0371(10) -0.0218(8) 0.0135(9) -0.0007(9) C17 0.0185(9) 0.0131(8) 0.0150(9) -0.0021(6) 0.0053(7) -0.0022(7) C8 0.0180(9) 0.0145(8) 0.0182(9) -0.0020(7) 0.0054(8) -0.0034(7) N2 0.0174(8) 0.0235(8) 0.0198(8) 0.0015(6) 0.0033(7) -0.0029(6) C28 0.0362(15) 0.0455(15) 0.0503(16) -0.0133(12) 0.0104(13) -0.0142(12) C24 0.0290(13) 0.0296(12) 0.0429(14) 0.0075(10) 0.0005(11) 0.0080(10) C21 0.0233(11) 0.0225(9) 0.0223(10) -0.0004(8) 0.0043(9) 0.0041(8) C22 0.0244(10) 0.0177(9) 0.0222(10) 0.0004(7) 0.0060(8) 0.0001(8) C23 0.0170(9) 0.0172(8) 0.0195(9) -0.0015(7) 0.0059(8) -0.0011(7) C18 0.0182(9) 0.0162(8) 0.0148(9) -0.0031(7) 0.0058(7) -0.0009(7) C15 0.0198(9) 0.0129(8) 0.0125(8) 0.0000(6) 0.0038(7) 0.0008(7) C16 0.0209(10) 0.0152(8) 0.0135(9) -0.0029(7) 0.0037(7) -0.0009(7) C7 0.0175(9) 0.0135(8) 0.0158(9) -0.0005(7) 0.0051(7) -0.0015(7) C19 0.0205(10) 0.0199(9) 0.0286(11) -0.0034(8) 0.0054(9) -0.0051(8) C20 0.0159(10) 0.0282(10) 0.0289(11) -0.0037(8) 0.0008(9) -0.0005(8) C14 0.0217(10) 0.0138(8) 0.0136(9) 0.0001(7) 0.0044(8) 0.0022(7) C9 0.0219(10) 0.0200(9) 0.0172(9) 0.0005(7) 0.0046(8) 0.0030(7) C10 0.0244(11) 0.0307(11) 0.0230(10) 0.0035(8) 0.0016(9) 0.0083(9) C11 0.0363(13) 0.0330(11) 0.0204(10) 0.0110(9) 0.0036(9) 0.0134(10) C12 0.0389(13) 0.0248(10) 0.0240(11) 0.0095(8) 0.0133(10) 0.0060(9) C13 0.0271(11) 0.0198(9) 0.0199(10) 0.0033(7) 0.0096(9) 0.0033(8) C1 0.0214(10) 0.0148(9) 0.0209(10) -0.0009(7) 0.0080(8) -0.0018(7) C6 0.0166(9) 0.0141(8) 0.0204(9) -0.0016(7) 0.0074(8) -0.0012(7) C5 0.0234(10) 0.0209(9) 0.0196(10) 0.0008(7) 0.0086(8) 0.0006(8) C4 0.0326(12) 0.0225(10) 0.0283(11) 0.0078(8) 0.0156(10) 0.0030(8) C3 0.0374(13) 0.0145(9) 0.0401(13) 0.0028(8) 0.0194(11) -0.0020(8) C2 0.0365(12) 0.0143(9) 0.0305(11) -0.0049(8) 0.0151(10) -0.0055(8) C27 0.064(2) 0.0482(16) 0.0486(17) 0.0063(13) 0.0221(16) -0.0015(14) C26 0.0464(15) 0.0396(13) 0.0345(13) -0.0162(10) 0.0170(12) -0.0044(11) C25 0.0535(18) 0.0551(18) 0.0453(16) -0.0026(13) 0.0135(14) 0.0068(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S2 O2 1.5120(17) . ? S2 C28 1.770(3) . ? S2 C27 1.774(3) . ? S1 O1 1.4958(19) . ? S1 C26 1.772(3) . ? S1 C25 1.784(3) . ? N1 C1 1.374(2) . ? N1 C8 1.384(2) . ? N1 H01 0.88 . ? C17 C7 1.506(2) . ? C17 C15 1.509(3) 2_556 ? C17 C18 1.532(3) . ? C17 H17A 1.00(2) . ? C8 C7 1.370(3) . ? C8 C16 1.472(3) . ? N2 C9 1.367(3) . ? N2 C16 1.383(2) . ? N2 H02 0.88 . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C24 C21 1.508(3) . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? C21 C20 1.389(3) . ? C21 C22 1.390(3) . ? C22 C23 1.394(3) . ? C22 H22 0.95 . ? C23 C18 1.387(3) . ? C23 H23 0.95 . ? C18 C19 1.391(3) . ? C15 C16 1.378(3) . ? C15 C14 1.442(2) . ? C15 C17 1.509(3) 2_556 ? C7 C6 1.433(2) . ? C19 C20 1.381(3) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C14 C13 1.399(3) . ? C14 C9 1.407(3) . ? C9 C10 1.400(3) . ? C10 C11 1.379(3) . ? C10 H10 0.95 . ? C11 C12 1.398(3) . ? C11 H11 0.95 . ? C12 C13 1.383(3) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C1 C2 1.397(3) . ? C1 C6 1.407(3) . ? C6 C5 1.404(3) . ? C5 C4 1.383(3) . ? C5 H5 0.95 . ? C4 C3 1.403(3) . ? C4 H4 0.95 . ? C3 C2 1.379(3) . ? C3 H3 0.95 . ? C2 H2 0.95 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? 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 O2 S2 C28 105.71(12) . . ? O2 S2 C27 105.24(13) . . ? C28 S2 C27 98.72(15) . . ? O1 S1 C26 106.46(12) . . ? O1 S1 C25 106.11(13) . . ? C26 S1 C25 98.00(14) . . ? C1 N1 C8 108.69(15) . . ? C1 N1 H01 125.7 . . ? C8 N1 H01 125.7 . . ? C7 C17 C15 113.76(15) . 2_556 ? C7 C17 C18 111.95(15) . . ? C15 C17 C18 115.55(15) 2_556 . ? C7 C17 H17A 105.6(13) . . ? C15 C17 H17A 103.3(13) 2_556 . ? C18 C17 H17A 105.4(13) . . ? C7 C8 N1 109.68(16) . . ? C7 C8 C16 130.40(17) . . ? N1 C8 C16 119.91(16) . . ? C9 N2 C16 109.05(16) . . ? C9 N2 H02 125.5 . . ? C16 N2 H02 125.5 . . ? S2 C28 H28A 109.5 . . ? S2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? S2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C21 C22 117.84(18) . . ? C20 C21 C24 120.6(2) . . ? C22 C21 C24 121.56(19) . . ? C21 C22 C23 121.29(18) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C18 C23 C22 120.54(18) . . ? C18 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C18 C19 117.96(17) . . ? C23 C18 C17 123.25(17) . . ? C19 C18 C17 118.76(16) . . ? C16 C15 C14 105.98(17) . . ? C16 C15 C17 129.83(16) . 2_556 ? C14 C15 C17 123.60(16) . 2_556 ? C15 C16 N2 109.72(16) . . ? C15 C16 C8 131.31(17) . . ? N2 C16 C8 118.91(17) . . ? C8 C7 C6 106.62(16) . . ? C8 C7 C17 128.85(16) . . ? C6 C7 C17 124.53(16) . . ? C20 C19 C18 121.48(18) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 120.89(19) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C13 C14 C9 119.48(17) . . ? C13 C14 C15 133.15(19) . . ? C9 C14 C15 107.32(16) . . ? N2 C9 C10 129.7(2) . . ? N2 C9 C14 107.92(16) . . ? C10 C9 C14 122.19(19) . . ? C11 C10 C9 116.9(2) . . ? C11 C10 H10 121.6 . . ? C9 C10 H10 121.6 . . ? C10 C11 C12 121.8(2) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C13 C12 C11 121.2(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 118.4(2) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? N1 C1 C2 129.97(18) . . ? N1 C1 C6 107.77(16) . . ? C2 C1 C6 122.25(18) . . ? C5 C6 C1 118.87(17) . . ? C5 C6 C7 133.93(17) . . ? C1 C6 C7 107.21(16) . . ? C4 C5 C6 119.01(18) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C4 C3 121.02(19) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C2 C3 C4 121.23(18) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C2 C1 117.60(19) . . ? C3 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? S2 C27 H27A 109.5 . . ? S2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? S2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? S1 C26 H26A 109.5 . . ? S1 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? S1 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? S1 C25 H25A 109.5 . . ? S1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C8 C7 1.7(2) . . . . ? C1 N1 C8 C16 -179.42(17) . . . . ? C20 C21 C22 C23 0.8(3) . . . . ? C24 C21 C22 C23 -179.4(2) . . . . ? C21 C22 C23 C18 -1.2(3) . . . . ? C22 C23 C18 C19 1.0(3) . . . . ? C22 C23 C18 C17 179.00(17) . . . . ? C7 C17 C18 C23 131.88(18) . . . . ? C15 C17 C18 C23 -0.5(3) 2_556 . . . ? C7 C17 C18 C19 -50.2(2) . . . . ? C15 C17 C18 C19 177.44(17) 2_556 . . . ? C14 C15 C16 N2 -1.0(2) . . . . ? C17 C15 C16 N2 170.22(17) 2_556 . . . ? C14 C15 C16 C8 -178.10(18) . . . . ? C17 C15 C16 C8 -6.9(3) 2_556 . . . ? C9 N2 C16 C15 1.1(2) . . . . ? C9 N2 C16 C8 178.62(16) . . . . ? C7 C8 C16 C15 -74.0(3) . . . . ? N1 C8 C16 C15 107.4(2) . . . . ? C7 C8 C16 N2 109.1(2) . . . . ? N1 C8 C16 N2 -69.5(2) . . . . ? N1 C8 C7 C6 -1.9(2) . . . . ? C16 C8 C7 C6 179.43(19) . . . . ? N1 C8 C7 C17 177.35(18) . . . . ? C16 C8 C7 C17 -1.4(4) . . . . ? C15 C17 C7 C8 91.3(2) 2_556 . . . ? C18 C17 C7 C8 -42.0(3) . . . . ? C15 C17 C7 C6 -89.7(2) 2_556 . . . ? C18 C17 C7 C6 137.06(18) . . . . ? C23 C18 C19 C20 -0.5(3) . . . . ? C17 C18 C19 C20 -178.53(19) . . . . ? C18 C19 C20 C21 0.1(3) . . . . ? C22 C21 C20 C19 -0.2(3) . . . . ? C24 C21 C20 C19 180.0(2) . . . . ? C16 C15 C14 C13 177.78(19) . . . . ? C17 C15 C14 C13 5.8(3) 2_556 . . . ? C16 C15 C14 C9 0.6(2) . . . . ? C17 C15 C14 C9 -171.37(16) 2_556 . . . ? C16 N2 C9 C10 -175.9(2) . . . . ? C16 N2 C9 C14 -0.7(2) . . . . ? C13 C14 C9 N2 -177.57(17) . . . . ? C15 C14 C9 N2 0.1(2) . . . . ? C13 C14 C9 C10 -1.9(3) . . . . ? C15 C14 C9 C10 175.74(18) . . . . ? N2 C9 C10 C11 176.1(2) . . . . ? C14 C9 C10 C11 1.5(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C9 C14 C13 C12 1.0(3) . . . . ? C15 C14 C13 C12 -176.0(2) . . . . ? C8 N1 C1 C2 -179.5(2) . . . . ? C8 N1 C1 C6 -0.8(2) . . . . ? N1 C1 C6 C5 179.60(17) . . . . ? C2 C1 C6 C5 -1.6(3) . . . . ? N1 C1 C6 C7 -0.3(2) . . . . ? C2 C1 C6 C7 178.52(19) . . . . ? C8 C7 C6 C5 -178.6(2) . . . . ? C17 C7 C6 C5 2.2(3) . . . . ? C8 C7 C6 C1 1.3(2) . . . . ? C17 C7 C6 C1 -177.93(17) . . . . ? C1 C6 C5 C4 1.4(3) . . . . ? C7 C6 C5 C4 -178.8(2) . . . . ? C6 C5 C4 C3 -0.1(3) . . . . ? C5 C4 C3 C2 -1.0(4) . . . . ? C4 C3 C2 C1 0.8(3) . . . . ? N1 C1 C2 C3 179.0(2) . . . . ? C6 C1 C2 C3 0.5(3) . . . . ?