# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- CCDC 761161-66.cif' _publ_contact_author_name 'Gopal Das' _publ_contact_author_address ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; _publ_contact_author_email gdas@iitg.ernet.in _publ_contact_author_phone 00913612582313 _publ_contact_author_fax 00913612582349 loop_ _publ_author_name _publ_author_address 'Sandeep Dey' . 'Ojha Bimlesh' . G.Das ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; data_nitro-HCl _database_code_depnum_ccdc_archive 'CCDC 761161' #TrackingRef '- CCDC 761161-66.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H25 N4 O9, Cl' _chemical_formula_sum 'C24 H25 Cl N4 O9' _chemical_formula_weight 548.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.475(6) _cell_length_b 13.365(10) _cell_length_c 13.784(10) _cell_angle_alpha 98.90(4) _cell_angle_beta 102.77(3) _cell_angle_gamma 105.84(5) _cell_volume 1257.6(17) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1270 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 18.45 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8173 _diffrn_reflns_av_R_equivalents 0.1018 _diffrn_reflns_av_sigmaI/netI 0.1515 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 23.56 _reflns_number_total 3753 _reflns_number_gt 3570 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0405P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0078(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3172 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 0.810 _refine_ls_restrained_S_all 0.810 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.14510(17) 0.02489(10) 0.84487(9) 0.0569(4) Uani 1 1 d . . . C5 C -0.1171(7) 0.8701(3) 0.4953(4) 0.0478(13) Uani 1 1 d . . . H5 H -0.2190 0.8841 0.5170 0.057 Uiso 1 1 calc R . . C2 C 0.4308(6) 0.9236(4) 0.6984(3) 0.0491(13) Uani 1 1 d . . . H2A H 0.3780 0.8618 0.7244 0.059 Uiso 1 1 calc R . . H2B H 0.3762 0.9788 0.7188 0.059 Uiso 1 1 calc R . . C1 C 0.6482(6) 0.9638(3) 0.7357(3) 0.0421(12) Uani 1 1 d . . . H1A H 0.6991 0.9186 0.6949 0.051 Uiso 1 1 calc R . . H1B H 0.6939 1.0355 0.7252 0.051 Uiso 1 1 calc R . . C3 C 0.2106(7) 0.8730(4) 0.5302(4) 0.0460(13) Uani 1 1 d . . . C6 C -0.1424(7) 0.8273(3) 0.3932(4) 0.0425(12) Uani 1 1 d . . . C4 C 0.0625(7) 0.8920(3) 0.5655(4) 0.0474(13) Uani 1 1 d . . . H4 H 0.0814 0.9188 0.6347 0.057 Uiso 1 1 calc R . . C7 C 0.0050(7) 0.8063(4) 0.3592(4) 0.0560(14) Uani 1 1 d . . . H7 H -0.0149 0.7762 0.2906 0.067 Uiso 1 1 calc R . . C8 C 0.1811(7) 0.8298(4) 0.4273(4) 0.0600(15) Uani 1 1 d . . . H8 H 0.2829 0.8169 0.4048 0.072 Uiso 1 1 calc R . . N1 N 0.7267(6) 0.9662(3) 0.8459(3) 0.0370(9) Uani 1 1 d . . . N2 N -0.3278(6) 0.8023(4) 0.3202(4) 0.0528(12) Uani 1 1 d . . . O1 O 0.3937(4) 0.8954(3) 0.5892(2) 0.0579(10) Uani 1 1 d . . . O2 O -0.3641(5) 0.7425(3) 0.2385(3) 0.0737(12) Uani 1 1 d . . . O3 O -0.4427(5) 0.8446(3) 0.3456(3) 0.0720(11) Uani 1 1 d . . . C16 C 0.8458(7) 1.3559(4) 0.8786(4) 0.0541(14) Uani 1 1 d . . . H16 H 0.7122 1.3297 0.8665 0.065 Uiso 1 1 calc R . . C9 C 0.6550(6) 1.0337(3) 0.9160(3) 0.0448(13) Uani 1 1 d . . . H9A H 0.7179 1.0355 0.9860 0.054 Uiso 1 1 calc R . . H9B H 0.5172 0.9999 0.9041 0.054 Uiso 1 1 calc R . . C14 C 1.1276(9) 1.4946(4) 0.8878(4) 0.0518(14) Uani 1 1 d . . . C11 C 0.9594(7) 1.2934(4) 0.9081(3) 0.0439(12) Uani 1 1 d . . . C12 C 1.1565(7) 1.3326(4) 0.9250(3) 0.0507(13) Uani 1 1 d . . . H12 H 1.2328 1.2904 0.9438 0.061 Uiso 1 1 calc R . . C10 C 0.6892(6) 1.1465(3) 0.9038(4) 0.0498(13) Uani 1 1 d . . . H10A H 0.6222 1.1472 0.8352 0.060 Uiso 1 1 calc R . . H10B H 0.6420 1.1858 0.9521 0.060 Uiso 1 1 calc R . . C15 C 0.9313(8) 1.4569(4) 0.8674(4) 0.0575(14) Uani 1 1 d . . . H15 H 0.8563 1.4989 0.8461 0.069 Uiso 1 1 calc R . . C13 C 1.2407(8) 1.4329(4) 0.9145(4) 0.0565(14) Uani 1 1 d . . . H13 H 1.3739 1.4591 0.9254 0.068 Uiso 1 1 calc R . . O4 O 0.8911(4) 1.1933(2) 0.9224(2) 0.0501(9) Uani 1 1 d . . . O5 O 1.3957(7) 1.6415(3) 0.9156(3) 0.0872(14) Uani 1 1 d . . . O6 O 1.1195(7) 1.6553(3) 0.8495(3) 0.0906(14) Uani 1 1 d . . . N3 N 1.2208(9) 1.6045(4) 0.8833(3) 0.0641(13) Uani 1 1 d . . . C17 C 0.6919(7) 0.8563(3) 0.8706(3) 0.0492(13) Uani 1 1 d . . . H17A H 0.7620 0.8652 0.9412 0.059 Uiso 1 1 calc R . . H17B H 0.5552 0.8258 0.8643 0.059 Uiso 1 1 calc R . . C19 C 0.6380(10) 0.6861(4) 0.6266(5) 0.0634(16) Uani 1 1 d . . . C18 C 0.7508(8) 0.7794(4) 0.8050(4) 0.0621(15) Uani 1 1 d . . . H18A H 0.8727 0.8152 0.7929 0.075 Uiso 1 1 calc R . . H18B H 0.7669 0.7222 0.8381 0.075 Uiso 1 1 calc R . . C20 C 0.8025(9) 0.6580(4) 0.6290(5) 0.0746(18) Uani 1 1 d . . . H20 H 0.8979 0.6716 0.6900 0.089 Uiso 1 1 calc R . . C24 C 0.4958(9) 0.6647(4) 0.5358(5) 0.0685(16) Uani 1 1 d . . . H24 H 0.3854 0.6841 0.5357 0.082 Uiso 1 1 calc R . . C22 C 0.6777(15) 0.5873(5) 0.4483(7) 0.091(2) Uani 1 1 d . . . C21 C 0.8209(11) 0.6080(5) 0.5363(7) 0.090(2) Uani 1 1 d . . . H21 H 0.9312 0.5890 0.5349 0.108 Uiso 1 1 calc R . . C23 C 0.5158(12) 0.6151(4) 0.4460(5) 0.085(2) Uani 1 1 d . . . H23 H 0.4205 0.6008 0.3849 0.102 Uiso 1 1 calc R . . O7 O 0.6020(5) 0.7370(3) 0.7104(3) 0.0624(10) Uani 1 1 d . . . N4 N 0.7031(16) 0.5319(6) 0.3515(6) 0.0608(6) Uani 1 1 d . . . O8 O 0.5638(12) 0.5098(5) 0.2751(5) 0.0557(5) Uani 1 1 d . . . O9 O 0.8479(13) 0.5110(6) 0.3547(6) 0.0934(7) Uani 1 1 d . . . H1N H 0.885(5) 1.000(3) 0.861(3) 0.034(11) 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 Cl1 0.0447(8) 0.0778(10) 0.0472(9) 0.0119(7) 0.0099(7) 0.0214(7) C5 0.049(4) 0.050(3) 0.050(4) 0.019(3) 0.020(3) 0.016(3) C2 0.050(4) 0.066(4) 0.028(3) 0.007(3) 0.006(3) 0.018(3) C1 0.040(3) 0.050(3) 0.036(3) 0.008(2) 0.009(2) 0.015(2) C3 0.031(3) 0.059(3) 0.043(4) 0.011(3) 0.005(3) 0.011(3) C6 0.031(3) 0.049(3) 0.045(4) 0.016(3) 0.006(3) 0.009(2) C4 0.045(3) 0.055(3) 0.037(3) 0.010(3) 0.008(3) 0.012(3) C7 0.039(3) 0.081(4) 0.043(4) 0.007(3) 0.007(3) 0.021(3) C8 0.046(4) 0.100(4) 0.035(4) 0.007(3) 0.009(3) 0.031(3) N1 0.037(3) 0.042(2) 0.026(2) 0.0072(19) 0.0034(19) 0.0093(19) N2 0.032(3) 0.074(3) 0.057(4) 0.028(3) 0.011(3) 0.019(3) O1 0.040(2) 0.094(3) 0.032(2) 0.0015(19) 0.0013(17) 0.0224(19) O2 0.061(3) 0.093(3) 0.044(3) -0.011(2) -0.005(2) 0.019(2) O3 0.048(2) 0.110(3) 0.065(3) 0.025(2) 0.011(2) 0.036(2) C16 0.049(3) 0.056(4) 0.050(4) 0.003(3) 0.004(3) 0.018(3) C9 0.040(3) 0.054(3) 0.040(3) 0.008(3) 0.015(3) 0.012(3) C14 0.062(4) 0.039(3) 0.043(3) 0.002(3) 0.010(3) 0.005(3) C11 0.047(4) 0.040(3) 0.035(3) -0.002(3) 0.007(3) 0.007(3) C12 0.049(4) 0.050(4) 0.047(4) 0.006(3) 0.007(3) 0.015(3) C10 0.046(4) 0.046(3) 0.050(4) 0.005(3) 0.009(3) 0.011(3) C15 0.067(4) 0.049(4) 0.048(4) 0.004(3) 0.004(3) 0.018(3) C13 0.056(4) 0.053(4) 0.049(4) 0.000(3) 0.011(3) 0.007(3) O4 0.035(2) 0.048(2) 0.061(2) 0.0091(18) 0.0062(17) 0.0108(17) O5 0.073(3) 0.066(3) 0.096(3) 0.012(2) 0.012(3) -0.007(2) O6 0.113(4) 0.064(3) 0.095(3) 0.031(3) 0.016(3) 0.031(3) N3 0.085(4) 0.053(4) 0.046(3) 0.004(3) 0.013(3) 0.017(3) C17 0.062(3) 0.043(3) 0.039(3) 0.013(3) 0.006(3) 0.014(3) C19 0.081(5) 0.040(3) 0.063(5) 0.010(3) 0.026(4) 0.007(3) C18 0.075(4) 0.048(3) 0.054(4) 0.005(3) 0.007(3) 0.017(3) C20 0.093(5) 0.049(4) 0.084(5) 0.014(4) 0.035(4) 0.018(4) C24 0.092(5) 0.051(4) 0.052(4) 0.010(3) 0.014(4) 0.013(3) C22 0.145(8) 0.050(4) 0.087(7) 0.020(4) 0.059(6) 0.023(5) C21 0.115(6) 0.061(4) 0.115(7) 0.026(5) 0.068(6) 0.028(4) C23 0.140(7) 0.049(4) 0.048(5) 0.011(3) 0.021(4) 0.005(4) O7 0.068(3) 0.053(2) 0.053(3) -0.005(2) 0.009(2) 0.0131(19) N4 0.0748(15) 0.0479(15) 0.0519(16) 0.0084(13) 0.0182(13) 0.0122(12) O8 0.0824(12) 0.0424(11) 0.0453(11) 0.0155(9) 0.0225(9) 0.0174(9) O9 0.137(2) 0.0549(14) 0.0602(15) -0.0001(12) 0.0152(13) 0.0052(13) _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 1.385(6) . ? C5 C4 1.396(6) . ? C2 O1 1.439(5) . ? C2 C1 1.504(6) . ? C1 N1 1.495(5) . ? C3 O1 1.354(5) . ? C3 C4 1.371(6) . ? C3 C8 1.389(6) . ? C6 C7 1.367(6) . ? C6 N2 1.439(6) . ? C7 C8 1.360(6) . ? N1 C9 1.503(5) . ? N1 C17 1.524(5) . ? N2 O2 1.205(5) . ? N2 O3 1.231(5) . ? C16 C15 1.376(6) . ? C16 C11 1.388(6) . ? C9 C10 1.501(6) . ? C14 C15 1.362(6) . ? C14 C13 1.366(6) . ? C14 N3 1.462(7) . ? C11 O4 1.357(5) . ? C11 C12 1.374(6) . ? C12 C13 1.361(6) . ? C10 O4 1.414(5) . ? O5 N3 1.214(5) . ? O6 N3 1.214(5) . ? C17 C18 1.484(6) . ? C19 C20 1.376(7) . ? C19 O7 1.365(6) . ? C19 C24 1.383(7) . ? C18 O7 1.429(5) . ? C20 C21 1.400(8) . ? C24 C23 1.369(7) . ? C22 C23 1.355(9) . ? C22 C21 1.362(9) . ? C22 N4 1.499(10) . ? N4 O9 1.182(10) . ? N4 O8 1.238(9) . ? 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 C4 119.4(5) . . ? O1 C2 C1 103.1(3) . . ? N1 C1 C2 113.8(3) . . ? O1 C3 C4 124.5(5) . . ? O1 C3 C8 114.7(4) . . ? C4 C3 C8 120.8(5) . . ? C7 C6 C5 121.5(5) . . ? C7 C6 N2 118.3(5) . . ? C5 C6 N2 120.1(5) . . ? C3 C4 C5 118.5(5) . . ? C8 C7 C6 118.9(5) . . ? C7 C8 C3 120.7(5) . . ? C9 N1 C1 113.0(3) . . ? C9 N1 C17 108.9(3) . . ? C1 N1 C17 114.4(3) . . ? O2 N2 O3 123.1(4) . . ? O2 N2 C6 119.8(4) . . ? O3 N2 C6 117.1(5) . . ? C3 O1 C2 118.6(3) . . ? C15 C16 C11 119.8(5) . . ? N1 C9 C10 114.7(3) . . ? C15 C14 C13 121.7(5) . . ? C15 C14 N3 119.4(6) . . ? C13 C14 N3 118.9(6) . . ? O4 C11 C12 115.5(5) . . ? O4 C11 C16 124.9(5) . . ? C12 C11 C16 119.7(5) . . ? C13 C12 C11 120.3(5) . . ? O4 C10 C9 106.9(4) . . ? C14 C15 C16 119.0(5) . . ? C12 C13 C14 119.4(5) . . ? C11 O4 C10 118.7(4) . . ? O6 N3 O5 123.1(5) . . ? O6 N3 C14 118.5(6) . . ? O5 N3 C14 118.4(6) . . ? C18 C17 N1 115.0(4) . . ? C20 C19 O7 124.0(6) . . ? C20 C19 C24 120.9(6) . . ? O7 C19 C24 115.0(6) . . ? O7 C18 C17 107.7(4) . . ? C19 C20 C21 117.5(6) . . ? C23 C24 C19 120.7(7) . . ? C23 C22 C21 122.3(8) . . ? C23 C22 N4 119.8(9) . . ? C21 C22 N4 118.0(9) . . ? C22 C21 C20 120.1(7) . . ? C24 C23 C22 118.5(7) . . ? C19 O7 C18 120.2(4) . . ? O9 N4 O8 126.2(10) . . ? O9 N4 C22 118.7(10) . . ? O8 N4 C22 115.1(10) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 23.56 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.236 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.058 data_nitro-HBr _database_code_depnum_ccdc_archive 'CCDC 761162' #TrackingRef '- CCDC 761161-66.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H25 N4 O9, Br' _chemical_formula_sum 'C24 H25 Br N4 O9 ' _chemical_formula_weight 593.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6818(6) _cell_length_b 13.3835(11) _cell_length_c 13.8995(12) _cell_angle_alpha 99.08(1) _cell_angle_beta 103.12(5) _cell_angle_gamma 106.33(3) _cell_volume 1297.45(48) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3901 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 26.67 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 1.644 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.506 _exptl_absorpt_correction_T_max 0.591 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10614 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 28.34 _reflns_number_total 6469 _reflns_number_gt 6386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0497P)^2^+0.1564P] 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 ? _refine_ls_extinction_method none _refine_ls_number_reflns 5935 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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 O5 O 1.9370(2) 0.16011(17) 1.15321(14) 0.0637(5) Uani 1 1 d . . . O6 O 1.8660(2) 0.26334(16) 1.26152(14) 0.0636(5) Uani 1 1 d . . . O2 O 0.1073(4) -0.64415(17) 0.58193(19) 0.0862(7) Uani 1 1 d . . . O3 O 0.3770(4) -0.65774(18) 0.6513(2) 0.0956(8) Uani 1 1 d . . . O1 O 0.6167(2) -0.19360(12) 0.58082(13) 0.0471(4) Uani 1 1 d . . . O4 O 1.1084(2) 0.10508(14) 0.91675(11) 0.0493(4) Uani 1 1 d . . . O7 O 0.9056(3) 0.26356(13) 0.79640(13) 0.0582(4) Uani 1 1 d . . . O8 O 0.9210(10) 0.4929(3) 1.2222(4) 0.069(3) Uani 1 1 d . . . O9 O 0.6462(11) 0.4900(4) 1.1403(5) 0.065(3) Uani 1 1 d . . . N3 N 1.8267(2) 0.20148(16) 1.17948(15) 0.0444(4) Uani 1 1 d . . . N2 N 0.2789(4) -0.60706(19) 0.61646(19) 0.0678(7) Uani 1 1 d . . . N1 N 0.7863(2) 0.03500(13) 0.65975(12) 0.0328(4) Uani 1 1 d . . . H1N H 0.6569 0.0067 0.6411 0.039 Uiso 1 1 d R . . N4 N 0.7846(13) 0.4692(3) 1.1434(4) 0.049(2) Uani 1 1 d . . . C13 C 1.6105(3) 0.13146(17) 1.00774(16) 0.0397(5) Uani 1 1 d . . . H13 H 1.7081 0.1167 0.9855 0.048 Uiso 1 1 calc R . . C14 C 1.6399(3) 0.17560(17) 1.10822(16) 0.0375(5) Uani 1 1 d . . . C15 C 1.4987(3) 0.1973(2) 1.14497(16) 0.0467(5) Uani 1 1 d . . . H15 H 1.5225 0.2283 1.2134 0.056 Uiso 1 1 calc R . . C16 C 1.3222(3) 0.1719(2) 1.07812(16) 0.0494(6) Uani 1 1 d . . . H16 H 1.2241 0.1843 1.1015 0.059 Uiso 1 1 calc R . . C11 C 1.2896(3) 0.12784(18) 0.97576(15) 0.0392(5) Uani 1 1 d . . . C12 C 1.4345(3) 0.10888(17) 0.93917(16) 0.0394(5) Uani 1 1 d . . . H12 H 1.4137 0.0816 0.8702 0.047 Uiso 1 1 calc R . . C3 C 0.5465(3) -0.29463(17) 0.59420(16) 0.0404(5) Uani 1 1 d . . . C8 C 0.6565(3) -0.35659(19) 0.62558(18) 0.0484(6) Uani 1 1 d . . . H8 H 0.7876 -0.3300 0.6401 0.058 Uiso 1 1 calc R . . C7 C 0.5677(4) -0.4586(2) 0.63482(18) 0.0533(6) Uani 1 1 d . . . H7 H 0.6390 -0.5012 0.6558 0.064 Uiso 1 1 calc R . . C6 C 0.3737(4) -0.49670(18) 0.61289(17) 0.0498(6) Uani 1 1 d . . . C5 C 0.2642(3) -0.4345(2) 0.58385(18) 0.0519(6) Uani 1 1 d . . . H5 H 0.1334 -0.4609 0.5709 0.062 Uiso 1 1 calc R . . C4 C 0.3504(3) -0.33350(19) 0.57435(18) 0.0467(5) Uani 1 1 d . . . H4 H 0.2782 -0.2909 0.5547 0.056 Uiso 1 1 calc R . . C10 C 1.0717(3) 0.07563(19) 0.80924(15) 0.0420(5) Uani 1 1 d . . . H10A H 1.1225 0.0194 0.7898 0.050 Uiso 1 1 calc R . . H10B H 1.1266 0.1368 0.7836 0.050 Uiso 1 1 calc R . . C9 C 0.8573(3) 0.03610(17) 0.76924(15) 0.0354(4) Uani 1 1 d . . . H9A H 0.8089 -0.0359 0.7783 0.043 Uiso 1 1 calc R . . H9B H 0.8082 0.0817 0.8091 0.043 Uiso 1 1 calc R . . C17 C 0.8238(4) 0.14390(18) 0.63551(17) 0.0466(5) Uani 1 1 d . . . H17A H 0.9583 0.1748 0.6439 0.056 Uiso 1 1 calc R . . H17B H 0.7577 0.1348 0.5647 0.056 Uiso 1 1 calc R . . C18 C 0.7636(4) 0.2215(2) 0.70043(19) 0.0562(6) Uani 1 1 d . . . H18A H 0.7508 0.2790 0.6679 0.067 Uiso 1 1 calc R . . H18B H 0.6425 0.1851 0.7099 0.067 Uiso 1 1 calc R . . C1 C 0.8531(3) -0.03382(17) 0.58962(15) 0.0387(5) Uani 1 1 d . . . H1A H 0.7907 -0.0361 0.5199 0.046 Uiso 1 1 calc R . . H1B H 0.9880 -0.0004 0.6014 0.046 Uiso 1 1 calc R . . C2 C 0.8166(3) -0.14620(17) 0.60201(17) 0.0422(5) Uani 1 1 d . . . H2A H 0.8817 -0.1453 0.6739 0.051 Uiso 1 1 d R . . H2B H 0.8670 -0.1884 0.5590 0.051 Uiso 1 1 d R . . C19 C 0.8647(4) 0.31340(19) 0.8775(2) 0.0605(7) Uani 1 1 d . . . C24 C 0.7032(6) 0.3413(2) 0.8721(3) 0.0769(9) Uani 1 1 d . . . C20 C 1.0024(6) 0.3364(2) 0.9696(2) 0.0721(9) Uani 1 1 d . . . C23 C 0.6826(9) 0.3917(3) 0.9630(5) 0.057(3) Uani 1 1 d . . . C21 C 0.9758(8) 0.3874(2) 1.0570(3) 0.036(3) Uani 1 1 d . . . H21 H 1.0670 0.4034 1.1191 0.118 Uiso 1 1 calc R . . C22 C 0.8178(10) 0.4139(3) 1.0521(4) 0.053(3) Uani 1 1 d . . . Br1 Br 0.64852(3) 1.02883(2) 0.343585(17) 0.04732(10) Uani 1 1 d . . . H23 H 0.575(5) 0.407(3) 0.951(3) 0.084(11) Uiso 1 1 d . . . H20 H 1.120(5) 0.319(3) 0.969(3) 0.094(12) Uiso 1 1 d . . . H24 H 0.614(5) 0.326(3) 0.812(3) 0.080(11) 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 O2 0.0810(16) 0.0615(13) 0.0908(16) 0.0072(11) 0.0242(13) -0.0088(11) O3 0.122(2) 0.0586(13) 0.1040(19) 0.0303(13) 0.0247(16) 0.0255(14) O1 0.0317(7) 0.0427(9) 0.0611(10) 0.0068(7) 0.0075(7) 0.0110(6) O4 0.0343(8) 0.0804(11) 0.0291(8) 0.0038(7) 0.0031(6) 0.0223(8) O7 0.0661(11) 0.0470(10) 0.0483(10) -0.0034(8) 0.0097(9) 0.0120(8) O5 0.0408(9) 0.0976(14) 0.0605(11) 0.0206(10) 0.0131(8) 0.0346(9) O6 0.0422(9) 0.0799(13) 0.0489(11) -0.0038(9) -0.0049(8) 0.0147(9) O8 0.046(5) 0.050(6) 0.110(8) 0.021(5) 0.030(6) 0.004(4) O9 0.062(5) 0.040(5) 0.092(6) 0.012(5) 0.021(5) 0.034(4) N3 0.0328(9) 0.0565(12) 0.0433(11) 0.0197(9) 0.0079(8) 0.0116(8) N2 0.092(2) 0.0477(14) 0.0538(14) 0.0065(11) 0.0247(14) 0.0080(14) N1 0.0277(8) 0.0377(9) 0.0289(8) 0.0064(7) 0.0046(7) 0.0080(7) N4 0.058(6) 0.053(6) 0.047(6) 0.018(5) 0.024(5) 0.022(5) C13 0.0340(10) 0.0457(12) 0.0420(12) 0.0127(10) 0.0134(9) 0.0139(9) C14 0.0291(10) 0.0447(12) 0.0369(11) 0.0140(9) 0.0058(8) 0.0102(9) C15 0.0393(11) 0.0693(16) 0.0277(10) 0.0051(10) 0.0063(9) 0.0181(11) C16 0.0361(11) 0.0797(17) 0.0335(11) 0.0062(11) 0.0103(9) 0.0247(11) C11 0.0330(10) 0.0507(13) 0.0326(10) 0.0105(9) 0.0063(8) 0.0138(9) C12 0.0385(11) 0.0460(12) 0.0321(10) 0.0076(9) 0.0095(9) 0.0128(9) C3 0.0393(11) 0.0386(12) 0.0370(11) -0.0006(9) 0.0080(9) 0.0107(9) C8 0.0402(12) 0.0488(14) 0.0492(13) 0.0032(11) 0.0065(10) 0.0137(10) C7 0.0618(15) 0.0477(14) 0.0461(14) 0.0060(11) 0.0057(12) 0.0220(12) C6 0.0613(15) 0.0410(13) 0.0359(12) -0.0002(10) 0.0116(11) 0.0066(11) C5 0.0424(12) 0.0532(15) 0.0475(13) 0.0017(11) 0.0098(11) 0.0047(11) C4 0.0391(11) 0.0466(13) 0.0476(13) 0.0039(10) 0.0072(10) 0.0120(10) C10 0.0354(10) 0.0561(14) 0.0298(10) 0.0055(10) 0.0050(9) 0.0140(10) C9 0.0326(10) 0.0434(12) 0.0290(10) 0.0092(9) 0.0071(8) 0.0116(9) C17 0.0584(14) 0.0405(12) 0.0357(11) 0.0114(10) 0.0081(10) 0.0111(11) C18 0.0681(16) 0.0413(13) 0.0532(15) 0.0074(11) 0.0066(13) 0.0192(12) C1 0.0335(10) 0.0481(12) 0.0320(10) 0.0048(9) 0.0087(8) 0.0127(9) C2 0.0322(10) 0.0452(12) 0.0442(12) 0.0008(10) 0.0071(9) 0.0133(9) C19 0.086(2) 0.0307(12) 0.0599(17) 0.0045(11) 0.0294(15) 0.0078(13) C24 0.100(3) 0.0475(16) 0.092(3) 0.0162(17) 0.046(2) 0.0233(17) C20 0.110(3) 0.0385(14) 0.0538(17) 0.0053(12) 0.0250(18) 0.0049(16) C23 0.083(9) 0.038(6) 0.047(7) 0.002(5) 0.025(7) 0.014(6) C21 0.049(6) 0.031(5) 0.024(5) 0.010(4) 0.005(5) -0.003(5) C22 0.074(8) 0.043(7) 0.042(7) 0.009(6) 0.021(7) 0.010(6) Br1 0.03322(12) 0.06955(18) 0.04067(14) 0.00954(11) 0.01031(9) 0.02136(10) _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 O5 N3 1.224(2) . ? O6 N3 1.218(3) . ? O2 N2 1.218(3) . ? O3 N2 1.220(3) . ? O1 C3 1.367(3) . ? O1 C2 1.427(2) . ? O4 C11 1.366(2) . ? O4 C10 1.424(2) . ? O7 C19 1.362(3) . ? O7 C18 1.429(3) . ? O8 N4 1.258(10) . ? O9 N4 1.166(10) . ? N3 C14 1.459(3) . ? N2 C6 1.466(3) . ? N1 C9 1.492(2) . ? N1 C1 1.507(2) . ? N1 C17 1.511(3) . ? N1 H1N 0.9162 . ? N4 C22 1.476(6) . ? C13 C14 1.368(3) . ? C13 C12 1.386(3) . ? C13 H13 0.9300 . ? C14 C15 1.380(3) . ? C15 C16 1.374(3) . ? C15 H15 0.9300 . ? C16 C11 1.388(3) . ? C16 H16 0.9300 . ? C11 C12 1.392(3) . ? C12 H12 0.9300 . ? C3 C8 1.390(3) . ? C3 C4 1.394(3) . ? C8 C7 1.385(3) . ? C8 H8 0.9300 . ? C7 C6 1.375(4) . ? C7 H7 0.9300 . ? C6 C5 1.382(4) . ? C5 C4 1.369(3) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C10 C9 1.517(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C17 C18 1.506(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C1 C2 1.496(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 1.0071 . ? C2 H2B 0.9730 . ? C19 C24 1.383(5) . ? C19 C20 1.390(5) . ? C24 C23 1.399(6) . ? C24 H24 0.90(3) . ? C20 C21 1.382(5) . ? C20 H20 1.00(4) . ? C23 C22 1.352(8) . ? C23 H23 0.89(3) . ? C21 C22 1.347(7) . ? C21 H21 0.9300 . ? 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 C3 O1 C2 118.65(16) . . ? C11 O4 C10 117.97(15) . . ? C19 O7 C18 119.4(2) . . ? O6 N3 O5 123.25(19) . . ? O6 N3 C14 118.75(18) . . ? O5 N3 C14 118.00(19) . . ? O2 N2 O3 123.6(3) . . ? O2 N2 C6 118.4(3) . . ? O3 N2 C6 118.0(3) . . ? C9 N1 C1 113.90(15) . . ? C9 N1 C17 115.37(16) . . ? C1 N1 C17 108.53(16) . . ? C9 N1 H1N 107.6 . . ? C1 N1 H1N 106.7 . . ? C17 N1 H1N 103.9 . . ? O9 N4 O8 124.5(5) . . ? O9 N4 C22 122.2(9) . . ? O8 N4 C22 113.3(8) . . ? C14 C13 C12 119.64(19) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 122.27(19) . . ? C13 C14 N3 119.32(18) . . ? C15 C14 N3 118.41(19) . . ? C16 C15 C14 118.46(19) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C15 C16 C11 120.22(19) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O4 C11 C16 115.01(18) . . ? O4 C11 C12 124.22(18) . . ? C16 C11 C12 120.77(19) . . ? C13 C12 C11 118.59(19) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? O1 C3 C8 124.56(19) . . ? O1 C3 C4 114.79(19) . . ? C8 C3 C4 120.7(2) . . ? C7 C8 C3 118.9(2) . . ? C7 C8 H8 120.5 . . ? C3 C8 H8 120.5 . . ? C6 C7 C8 119.7(2) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C6 C5 121.5(2) . . ? C7 C6 N2 119.7(2) . . ? C5 C6 N2 118.7(2) . . ? C4 C5 C6 119.3(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? O4 C10 C9 104.10(16) . . ? O4 C10 H10A 110.9 . . ? C9 C10 H10A 110.9 . . ? O4 C10 H10B 110.9 . . ? C9 C10 H10B 110.9 . . ? H10A C10 H10B 109.0 . . ? N1 C9 C10 113.39(16) . . ? N1 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C18 C17 N1 114.23(19) . . ? C18 C17 H17A 108.7 . . ? N1 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? N1 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? O7 C18 C17 107.8(2) . . ? O7 C18 H18A 110.2 . . ? C17 C18 H18A 110.2 . . ? O7 C18 H18B 110.2 . . ? C17 C18 H18B 110.2 . . ? H18A C18 H18B 108.5 . . ? C2 C1 N1 114.38(17) . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? N1 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? O1 C2 C1 106.95(17) . . ? O1 C2 H2A 110.1 . . ? C1 C2 H2A 109.7 . . ? O1 C2 H2B 111.2 . . ? C1 C2 H2B 113.4 . . ? H2A C2 H2B 105.5 . . ? O7 C19 C24 124.8(3) . . ? O7 C19 C20 114.2(3) . . ? C24 C19 C20 121.0(3) . . ? C19 C24 C23 117.5(5) . . ? C19 C24 H24 120(2) . . ? C23 C24 H24 122(2) . . ? C21 C20 C19 119.1(4) . . ? C21 C20 H20 123(2) . . ? C19 C20 H20 118(2) . . ? C22 C23 C24 121.0(5) . . ? C22 C23 H23 129(3) . . ? C24 C23 H23 110(3) . . ? C22 C21 C20 120.0(4) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 121.4(4) . . ? C21 C22 N4 121.8(7) . . ? C23 C22 N4 116.8(7) . . ? 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 C12 C13 C14 C15 1.1(3) . . . . ? C12 C13 C14 N3 -178.56(19) . . . . ? O6 N3 C14 C13 162.1(2) . . . . ? O5 N3 C14 C13 -17.4(3) . . . . ? O6 N3 C14 C15 -17.5(3) . . . . ? O5 N3 C14 C15 162.9(2) . . . . ? C13 C14 C15 C16 1.0(4) . . . . ? N3 C14 C15 C16 -179.3(2) . . . . ? C14 C15 C16 C11 -1.5(4) . . . . ? C10 O4 C11 C16 170.4(2) . . . . ? C10 O4 C11 C12 -10.1(3) . . . . ? C15 C16 C11 O4 179.5(2) . . . . ? C15 C16 C11 C12 -0.1(4) . . . . ? C14 C13 C12 C11 -2.7(3) . . . . ? O4 C11 C12 C13 -177.3(2) . . . . ? C16 C11 C12 C13 2.2(3) . . . . ? C2 O1 C3 C8 -1.3(3) . . . . ? C2 O1 C3 C4 178.37(19) . . . . ? O1 C3 C8 C7 -179.1(2) . . . . ? C4 C3 C8 C7 1.3(3) . . . . ? C3 C8 C7 C6 0.1(3) . . . . ? C8 C7 C6 C5 -1.5(4) . . . . ? C8 C7 C6 N2 176.2(2) . . . . ? O2 N2 C6 C7 -168.9(2) . . . . ? O3 N2 C6 C7 9.0(4) . . . . ? O2 N2 C6 C5 8.9(3) . . . . ? O3 N2 C6 C5 -173.2(3) . . . . ? C7 C6 C5 C4 1.6(4) . . . . ? N2 C6 C5 C4 -176.1(2) . . . . ? C6 C5 C4 C3 -0.2(3) . . . . ? O1 C3 C4 C5 179.1(2) . . . . ? C8 C3 C4 C5 -1.3(3) . . . . ? C11 O4 C10 C9 169.59(19) . . . . ? C1 N1 C9 C10 58.8(2) . . . . ? C17 N1 C9 C10 -67.7(2) . . . . ? O4 C10 C9 N1 160.82(17) . . . . ? C9 N1 C17 C18 -50.8(3) . . . . ? C1 N1 C17 C18 -179.97(19) . . . . ? C19 O7 C18 C17 -163.1(2) . . . . ? N1 C17 C18 O7 79.0(3) . . . . ? C9 N1 C1 C2 52.6(2) . . . . ? C17 N1 C1 C2 -177.40(17) . . . . ? C3 O1 C2 C1 -175.20(17) . . . . ? N1 C1 C2 O1 60.3(2) . . . . ? C18 O7 C19 C24 -10.0(4) . . . . ? C18 O7 C19 C20 170.7(2) . . . . ? O7 C19 C24 C23 179.7(3) . . . . ? C20 C19 C24 C23 -1.1(4) . . . . ? O7 C19 C20 C21 179.7(2) . . . . ? C24 C19 C20 C21 0.4(4) . . . . ? C19 C24 C23 C22 1.2(5) . . . . ? C19 C20 C21 C22 0.2(5) . . . . ? C20 C21 C22 C23 -0.1(5) . . . . ? C20 C21 C22 N4 -179.5(3) . . . . ? C24 C23 C22 C21 -0.7(6) . . . . ? C24 C23 C22 N4 178.8(3) . . . . ? O9 N4 C22 C21 -178.0(5) . . . . ? O8 N4 C22 C21 3.5(5) . . . . ? O9 N4 C22 C23 2.5(7) . . . . ? O8 N4 C22 C23 -175.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.98 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.98 _refine_diff_density_max 0.423 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.050 data_nitro-HNO3 _database_code_depnum_ccdc_archive 'CCDC 761163' #TrackingRef '- CCDC 761161-66.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H25 N4 O9, N O3' _chemical_formula_sum 'C24 H25 N5 O12 ' _chemical_formula_weight 575.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.2304(7) _cell_length_b 8.9608(4) _cell_length_c 20.0560(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.073(3) _cell_angle_gamma 90.00 _cell_volume 2686.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1497 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 16.22 _exptl_crystal_description recetangular _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22545 _diffrn_reflns_av_R_equivalents 0.0733 _diffrn_reflns_av_sigmaI/netI 0.1735 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 28.27 _reflns_number_total 6659 _reflns_number_gt 6185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0250P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_number_reflns 6027 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2770 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.16395(18) 0.2159(3) 0.84253(15) 0.0650(9) Uani 1 1 d . . . C2 C 0.1647(2) 0.2417(3) 0.91630(16) 0.0730(10) Uani 1 1 d . . . C3 C 0.0565(2) 0.2671(4) 0.98854(18) 0.0631(9) Uani 1 1 d . . . C4 C 0.1163(2) 0.3366(4) 1.03925(18) 0.0690(10) Uani 1 1 d . . . C5 C 0.0863(2) 0.3936(3) 1.09484(17) 0.0725(10) Uani 1 1 d . . . C6 C -0.0023(2) 0.3786(4) 1.09866(18) 0.0612(9) Uani 1 1 d . . . C7 C -0.0620(2) 0.3078(4) 1.04844(19) 0.0729(10) Uani 1 1 d . . . C8 C -0.0327(2) 0.2523(4) 0.99328(16) 0.0735(10) Uani 1 1 d . . . C9 C 0.23288(18) -0.0421(3) 0.85097(14) 0.0679(9) Uani 1 1 d . . . C10 C 0.32234(19) 0.0119(4) 0.83820(16) 0.0755(10) Uani 1 1 d . . . C11 C 0.4415(2) 0.1712(4) 0.88842(18) 0.0679(10) Uani 1 1 d . . . C12 C 0.4864(2) 0.1466(4) 0.83649(16) 0.0722(10) Uani 1 1 d . . . C13 C 0.5680(2) 0.2153(4) 0.83708(19) 0.0819(11) Uani 1 1 d . . . C14 C 0.6035(2) 0.3056(4) 0.8895(2) 0.0819(12) Uani 1 1 d . . . C15 C 0.5610(3) 0.3290(4) 0.94228(18) 0.0969(13) Uani 1 1 d . . . C16 C 0.4786(2) 0.2647(4) 0.94137(18) 0.0914(12) Uani 1 1 d . . . C17 C 0.07083(19) -0.0231(3) 0.82313(14) 0.0690(9) Uani 1 1 d . . . C18 C -0.01356(19) 0.0621(3) 0.79513(16) 0.0715(10) Uani 1 1 d . . . C19 C -0.0783(2) 0.1947(4) 0.69527(19) 0.0660(10) Uani 1 1 d . . . C20 C -0.1507(2) 0.2370(4) 0.72332(16) 0.0728(10) Uani 1 1 d . . . C21 C -0.2118(2) 0.3337(4) 0.68819(19) 0.0753(10) Uani 1 1 d . . . C22 C -0.2019(2) 0.3876(4) 0.62620(19) 0.0680(10) Uani 1 1 d . . . C23 C -0.1304(2) 0.3446(4) 0.59786(16) 0.0778(11) Uani 1 1 d . . . C24 C -0.0681(2) 0.2476(4) 0.63290(19) 0.0771(11) Uani 1 1 d . . . N1 N 0.15585(16) 0.0565(3) 0.81883(15) 0.0605(8) Uani 1 1 d . . . N2 N -0.0336(2) 0.4436(4) 1.15674(16) 0.0793(9) Uani 1 1 d . . . N3 N 0.6903(2) 0.3774(4) 0.8895(2) 0.1091(13) Uani 1 1 d . . . N4 N -0.2670(2) 0.4927(4) 0.58920(18) 0.0892(10) Uani 1 1 d . . . N5 N 0.3225(2) 0.5386(5) 0.8444(2) 0.0920(11) Uani 1 1 d . . . O1 O 0.07789(13) 0.2138(2) 0.93014(11) 0.0827(7) Uani 1 1 d . . . O2 O 0.01730(18) 0.5228(3) 1.19549(13) 0.1121(10) Uani 1 1 d . . . O3 O -0.10955(17) 0.4142(3) 1.16400(12) 0.1016(9) Uani 1 1 d . . . O4 O 0.36066(14) 0.1111(2) 0.89212(10) 0.0748(7) Uani 1 1 d . . . O5 O 0.72349(19) 0.3620(4) 0.83990(17) 0.1516(14) Uani 1 1 d . . . O6 O 0.7212(2) 0.4511(4) 0.93750(18) 0.1694(16) Uani 1 1 d . . . O7 O -0.01291(13) 0.1002(3) 0.72662(11) 0.0762(7) Uani 1 1 d . . . O8 O -0.32785(19) 0.5310(3) 0.61760(13) 0.1347(12) Uani 1 1 d . . . O9 O -0.25880(17) 0.5356(3) 0.53374(13) 0.1105(10) Uani 1 1 d . . . O10 O 0.32050(15) 0.4256(3) 0.80844(13) 0.0948(9) Uani 1 1 d . . . O11 O 0.32750(16) 0.6604(3) 0.81411(15) 0.1110(10) Uani 1 1 d . . . O12 O 0.3185(2) 0.5326(4) 0.90350(14) 0.1510(14) Uani 1 1 d . . . H1N H 0.1647(17) 0.069(3) 0.7696(15) 0.093(12) Uiso 1 1 d . . . H1A H 0.2187 0.2568 0.8321 0.078 Uiso 1 1 calc R . . H1B H 0.1145 0.2718 0.8164 0.078 Uiso 1 1 calc R . . H2A H 0.2079 0.1758 0.9435 0.088 Uiso 1 1 calc R . . H2B H 0.1821 0.3439 0.9282 0.088 Uiso 1 1 calc R . . H4 H 0.1762 0.3451 1.0361 0.083 Uiso 1 1 calc R . . H5 H 0.1258 0.4417 1.1293 0.087 Uiso 1 1 calc R . . H7 H -0.1217 0.2978 1.0521 0.087 Uiso 1 1 calc R . . H8 H -0.0725 0.2046 0.9589 0.088 Uiso 1 1 calc R . . H9A H 0.2223 -0.1425 0.8332 0.081 Uiso 1 1 calc R . . H9B H 0.2350 -0.0464 0.8996 0.081 Uiso 1 1 calc R . . H10A H 0.3619 -0.0724 0.8366 0.091 Uiso 1 1 calc R . . H10B H 0.3143 0.0635 0.7950 0.091 Uiso 1 1 calc R . . H12 H 0.4621 0.0837 0.8008 0.087 Uiso 1 1 calc R . . H13 H 0.5983 0.1996 0.8016 0.098 Uiso 1 1 calc R . . H15 H 0.5873 0.3880 0.9788 0.116 Uiso 1 1 calc R . . H16 H 0.4478 0.2841 0.9763 0.110 Uiso 1 1 calc R . . H17A H 0.0712 -0.0465 0.8704 0.083 Uiso 1 1 calc R . . H17B H 0.0695 -0.1168 0.7988 0.083 Uiso 1 1 calc R . . H18A H -0.0655 0.0012 0.7976 0.086 Uiso 1 1 calc R . . H18B H -0.0165 0.1519 0.8217 0.086 Uiso 1 1 calc R . . H20 H -0.1576 0.2002 0.7654 0.087 Uiso 1 1 calc R . . H21 H -0.2607 0.3633 0.7065 0.090 Uiso 1 1 calc R . . H23 H -0.1243 0.3807 0.5555 0.093 Uiso 1 1 calc R . . H24 H -0.0193 0.2180 0.6145 0.093 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 C1 0.064(2) 0.048(3) 0.086(3) 0.006(2) 0.0228(19) -0.0030(18) C2 0.071(2) 0.070(3) 0.078(3) -0.006(2) 0.015(2) -0.004(2) C3 0.061(2) 0.064(3) 0.064(3) 0.002(2) 0.009(2) -0.006(2) C4 0.050(2) 0.074(3) 0.080(3) -0.006(2) 0.005(2) -0.0052(19) C5 0.067(3) 0.070(3) 0.074(3) -0.010(2) 0.000(2) -0.005(2) C6 0.066(3) 0.047(2) 0.068(3) 0.0055(19) 0.007(2) 0.001(2) C7 0.065(2) 0.080(3) 0.074(3) 0.014(2) 0.012(2) -0.011(2) C8 0.058(2) 0.095(3) 0.064(3) -0.005(2) 0.004(2) -0.029(2) C9 0.054(2) 0.057(2) 0.090(2) -0.0026(19) 0.0070(19) 0.0019(19) C10 0.056(2) 0.077(3) 0.093(3) -0.013(2) 0.014(2) -0.006(2) C11 0.059(2) 0.074(3) 0.071(3) 0.006(2) 0.013(2) -0.003(2) C12 0.057(2) 0.081(3) 0.076(3) -0.009(2) 0.005(2) -0.003(2) C13 0.061(3) 0.102(3) 0.084(3) 0.010(2) 0.018(2) 0.002(2) C14 0.069(3) 0.094(3) 0.081(3) 0.017(3) 0.010(3) -0.020(2) C15 0.093(3) 0.118(4) 0.076(3) -0.009(2) 0.006(2) -0.045(3) C16 0.089(3) 0.110(3) 0.079(3) -0.020(2) 0.025(2) -0.039(3) C17 0.061(2) 0.064(3) 0.080(2) 0.0015(19) 0.0080(19) -0.009(2) C18 0.052(2) 0.084(3) 0.075(3) 0.001(2) 0.0045(19) 0.0013(19) C19 0.050(2) 0.080(3) 0.064(3) -0.009(2) 0.001(2) 0.004(2) C20 0.055(2) 0.098(3) 0.063(2) 0.002(2) 0.007(2) 0.009(2) C21 0.054(2) 0.101(3) 0.071(3) -0.008(2) 0.013(2) 0.007(2) C22 0.060(2) 0.079(3) 0.064(3) -0.008(2) 0.007(2) 0.009(2) C23 0.076(3) 0.096(3) 0.059(2) -0.005(2) 0.008(2) 0.010(2) C24 0.060(3) 0.107(3) 0.066(3) -0.005(2) 0.014(2) 0.011(2) N1 0.0485(17) 0.061(2) 0.072(2) 0.0083(18) 0.0104(15) -0.0036(16) N2 0.087(3) 0.069(3) 0.081(3) -0.0011(19) 0.016(2) 0.005(2) N3 0.078(3) 0.123(4) 0.127(4) 0.009(3) 0.020(3) -0.028(2) N4 0.090(3) 0.094(3) 0.078(3) -0.011(2) 0.003(2) 0.021(2) N5 0.079(2) 0.083(3) 0.114(4) -0.006(3) 0.020(2) 0.000(2) O1 0.0656(16) 0.105(2) 0.0819(18) -0.0160(14) 0.0252(14) -0.0299(14) O2 0.127(2) 0.109(2) 0.104(2) -0.0338(17) 0.0324(17) -0.0293(18) O3 0.0846(18) 0.104(2) 0.124(2) -0.0049(15) 0.0394(17) 0.0058(17) O4 0.0655(16) 0.0808(18) 0.0787(16) -0.0069(13) 0.0151(13) -0.0161(13) O5 0.102(2) 0.193(3) 0.172(3) -0.009(3) 0.058(2) -0.040(2) O6 0.141(3) 0.208(4) 0.158(3) -0.038(3) 0.026(2) -0.108(3) O7 0.0635(15) 0.0991(19) 0.0638(16) 0.0020(14) 0.0068(13) 0.0153(14) O8 0.125(2) 0.177(3) 0.106(2) 0.0168(18) 0.0318(18) 0.081(2) O9 0.130(2) 0.122(2) 0.0748(19) 0.0086(18) 0.0072(18) 0.0356(17) O10 0.0989(19) 0.077(2) 0.110(2) 0.0135(17) 0.0231(16) -0.0090(16) O11 0.118(2) 0.065(2) 0.162(3) 0.0065(19) 0.0568(19) 0.0003(17) O12 0.164(3) 0.217(4) 0.073(2) -0.005(2) 0.026(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C17 1.495(3) . ? N1 C1 1.503(3) . ? N1 C9 1.511(3) . ? C3 O1 1.361(3) . ? C3 C4 1.377(4) . ? C3 C8 1.387(4) . ? C4 C5 1.381(3) . ? C6 C5 1.373(4) . ? C6 C7 1.376(4) . ? C6 N2 1.462(4) . ? C1 C2 1.495(3) . ? C8 C7 1.363(3) . ? C2 O1 1.424(3) . ? N2 O2 1.215(3) . ? N2 O3 1.222(3) . ? C9 C10 1.513(3) . ? C11 O4 1.359(3) . ? C11 C12 1.369(3) . ? C11 C16 1.385(4) . ? C16 C15 1.378(4) . ? C13 C14 1.355(4) . ? C13 C12 1.385(4) . ? C14 C15 1.359(4) . ? C14 N3 1.470(4) . ? C10 O4 1.435(3) . ? N3 O6 1.187(4) . ? N3 O5 1.208(4) . ? C19 O7 1.365(3) . ? C19 C24 1.374(4) . ? C19 C20 1.384(4) . ? C24 C23 1.376(4) . ? C22 C21 1.369(4) . ? C22 C23 1.377(4) . ? C22 N4 1.462(4) . ? C18 O7 1.418(3) . ? C18 C17 1.508(3) . ? C21 C20 1.364(4) . ? O9 N4 1.206(3) . ? O8 N4 1.227(3) . ? N5 O12 1.198(3) . ? N5 O10 1.240(3) . ? N5 O11 1.259(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C17 N1 C1 117.0(2) . . ? C17 N1 C9 107.9(2) . . ? C1 N1 C9 114.3(2) . . ? O1 C3 C4 124.1(3) . . ? O1 C3 C8 115.1(3) . . ? C4 C3 C8 120.7(3) . . ? C3 C4 C5 119.3(3) . . ? C5 C6 C7 121.5(3) . . ? C5 C6 N2 118.7(4) . . ? C7 C6 N2 119.8(4) . . ? C2 C1 N1 116.4(3) . . ? C6 C5 C4 119.3(3) . . ? C7 C8 C3 119.8(3) . . ? O1 C2 C1 109.5(2) . . ? C8 C7 C6 119.3(3) . . ? C3 O1 C2 119.4(2) . . ? O2 N2 O3 123.5(4) . . ? O2 N2 C6 118.5(3) . . ? O3 N2 C6 118.0(3) . . ? N1 C9 C10 113.0(2) . . ? O4 C11 C12 124.6(3) . . ? O4 C11 C16 115.9(3) . . ? C12 C11 C16 119.5(3) . . ? C15 C16 C11 119.9(3) . . ? C14 C13 C12 119.8(3) . . ? C13 C14 C15 121.1(4) . . ? C13 C14 N3 119.1(4) . . ? C15 C14 N3 119.8(4) . . ? C14 C15 C16 119.7(4) . . ? C11 C12 C13 120.0(3) . . ? O4 C10 C9 108.6(2) . . ? O6 N3 O5 124.6(4) . . ? O6 N3 C14 117.4(4) . . ? O5 N3 C14 118.0(4) . . ? C11 O4 C10 116.5(2) . . ? O7 C19 C24 115.7(3) . . ? O7 C19 C20 123.4(3) . . ? C24 C19 C20 120.9(3) . . ? C19 C24 C23 119.7(3) . . ? C21 C22 C23 120.7(4) . . ? C21 C22 N4 120.4(4) . . ? C23 C22 N4 118.9(4) . . ? O7 C18 C17 108.6(2) . . ? C20 C21 C22 120.7(3) . . ? C21 C20 C19 118.8(3) . . ? C24 C23 C22 119.2(3) . . ? N1 C17 C18 115.0(2) . . ? C19 O7 C18 117.1(3) . . ? O9 N4 O8 124.1(4) . . ? O9 N4 C22 119.6(4) . . ? O8 N4 C22 116.3(3) . . ? O12 N5 O10 122.6(4) . . ? O12 N5 O11 122.3(4) . . ? O10 N5 O11 115.0(4) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.253 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.038 data_nitro-HClO4 _database_code_depnum_ccdc_archive 'CCDC 761164' #TrackingRef '- CCDC 761161-66.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H25 N4 O9, Cl O4' _chemical_formula_sum 'C24 H25 Cl N4 O13 ' _chemical_formula_weight 612.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 11.9923(5) _cell_length_b 12.5750(6) _cell_length_c 18.0740(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.045(2) _cell_angle_gamma 90.00 _cell_volume 2655.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5086 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 19.70 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38561 _diffrn_reflns_av_R_equivalents 0.0784 _diffrn_reflns_av_sigmaI/netI 0.1035 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.39 _reflns_number_total 6585 _reflns_number_gt 5805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0234P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_number_reflns 6585 _refine_ls_number_parameters 384 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1650 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.54627(18) -0.01606(18) 0.28054(12) 0.0594(7) Uani 1 1 d . . . C2 C 0.66150(19) -0.05152(18) 0.32526(13) 0.0613(7) Uani 1 1 d . . . C3 C 0.8516(2) 0.0160(2) 0.35279(12) 0.0505(6) Uani 1 1 d . . . C4 C 0.9216(2) 0.1016(2) 0.34805(12) 0.0628(7) Uani 1 1 d . . . C5 C 1.0371(2) 0.0957(2) 0.37999(14) 0.0704(8) Uani 1 1 d . . . C6 C 1.0798(2) 0.0033(3) 0.41704(14) 0.0662(8) Uani 1 1 d . . . C7 C 1.0120(2) -0.0813(2) 0.42269(13) 0.0695(8) Uani 1 1 d . . . C8 C 0.8965(2) -0.0762(2) 0.39041(13) 0.0616(7) Uani 1 1 d . . . C9 C 0.39897(17) 0.12488(17) 0.25161(12) 0.0546(6) Uani 1 1 d . . . C10 C 0.30342(17) 0.04416(18) 0.24736(12) 0.0593(7) Uani 1 1 d . . . C11 C 0.1013(2) 0.0398(2) 0.20008(12) 0.0512(6) Uani 1 1 d . . . C12 C 0.0965(2) -0.0634(2) 0.22529(12) 0.0566(7) Uani 1 1 d . . . C13 C -0.0079(2) -0.11369(19) 0.21419(12) 0.0587(7) Uani 1 1 d . . . C14 C -0.1043(2) -0.0613(2) 0.17746(12) 0.0510(6) Uani 1 1 d . . . C15 C -0.1014(2) 0.0413(2) 0.15238(12) 0.0556(7) Uani 1 1 d . . . C16 C 0.0026(2) 0.09306(19) 0.16375(12) 0.0566(7) Uani 1 1 d . . . C17 C 0.50356(18) 0.09774(18) 0.38667(12) 0.0569(7) Uani 1 1 d . . . C18 C 0.51278(19) 0.21202(19) 0.41405(12) 0.0626(7) Uani 1 1 d . . . C19 C 0.6624(2) 0.3452(2) 0.42836(12) 0.0532(6) Uani 1 1 d . . . C20 C 0.7791(2) 0.3586(2) 0.43975(12) 0.0588(7) Uani 1 1 d . . . C21 C 0.8250(2) 0.4580(2) 0.45577(11) 0.0606(7) Uani 1 1 d . . . C22 C 0.7531(3) 0.5424(2) 0.45848(12) 0.0587(7) Uani 1 1 d . . . C23 C 0.6371(2) 0.5294(2) 0.44803(12) 0.0647(7) Uani 1 1 d . . . C24 C 0.5907(2) 0.4296(2) 0.43338(12) 0.0592(7) Uani 1 1 d . . . N1 N 0.50887(17) 0.09103(16) 0.30442(11) 0.0511(5) Uani 1 1 d . . . N2 N 1.2027(2) 0.0001(3) 0.45186(15) 0.0940(10) Uani 1 1 d . . . N3 N -0.2142(2) -0.1149(2) 0.16632(13) 0.0707(7) Uani 1 1 d . . . N4 N 0.8027(3) 0.6488(2) 0.47230(14) 0.0863(8) Uani 1 1 d . . . O1 O 0.73970(13) 0.02996(12) 0.31865(8) 0.0609(4) Uani 1 1 d . . . O2 O 1.23577(17) -0.0747(2) 0.49544(12) 0.1258(9) Uani 1 1 d . . . O3 O 1.26430(18) 0.0682(2) 0.43757(14) 0.1312(10) Uani 1 1 d . . . O4 O 0.20177(13) 0.09616(12) 0.20855(8) 0.0607(5) Uani 1 1 d . . . O5 O -0.21750(16) -0.20259(19) 0.19381(13) 0.1243(9) Uani 1 1 d . . . O6 O -0.29927(16) -0.07105(16) 0.13149(11) 0.1012(7) Uani 1 1 d . . . O7 O 0.62545(13) 0.24354(13) 0.40999(8) 0.0673(5) Uani 1 1 d . . . O8 O 0.7358(2) 0.72355(18) 0.45991(15) 0.1436(10) Uani 1 1 d . . . O9 O 0.9055(2) 0.65924(16) 0.49252(12) 0.1052(7) Uani 1 1 d . . . O10 O 0.5769(2) 0.33473(19) 0.11534(10) 0.1561(10) Uani 1 1 d . . . O11 O 0.59773(16) 0.15310(17) 0.13054(12) 0.1334(8) Uani 1 1 d . . . O12 O 0.62066(15) 0.26431(12) 0.23557(9) 0.0934(6) Uani 1 1 d . . . O13 O 0.75251(19) 0.26188(17) 0.16068(13) 0.1416(9) Uani 1 1 d . . . H1N H 0.5665(18) 0.1355(17) 0.2951(11) 0.078(9) Uiso 1 1 d . . . H1A H 0.4897 -0.0689 0.2860 0.071 Uiso 1 1 calc R . . H1B H 0.5482 -0.0128 0.2272 0.071 Uiso 1 1 calc R . . H2A H 0.6596 -0.0623 0.3781 0.074 Uiso 1 1 calc R . . H2B H 0.6836 -0.1178 0.3051 0.074 Uiso 1 1 calc R . . H4 H 0.8908 0.1634 0.3233 0.075 Uiso 1 1 calc R . . H5 H 1.0853 0.1526 0.3767 0.084 Uiso 1 1 calc R . . H7 H 1.0434 -0.1424 0.4482 0.083 Uiso 1 1 calc R . . H8 H 0.8492 -0.1337 0.3938 0.074 Uiso 1 1 calc R . . H9A H 0.4125 0.1353 0.2012 0.065 Uiso 1 1 calc R . . H9B H 0.3749 0.1925 0.2687 0.065 Uiso 1 1 calc R . . H10A H 0.3177 -0.0187 0.2197 0.071 Uiso 1 1 calc R . . H10B H 0.2973 0.0230 0.2979 0.071 Uiso 1 1 calc R . . H12 H 0.1630 -0.0985 0.2495 0.068 Uiso 1 1 calc R . . H13 H -0.0128 -0.1828 0.2316 0.070 Uiso 1 1 calc R . . H15 H -0.1685 0.0755 0.1281 0.067 Uiso 1 1 calc R . . H16 H 0.0066 0.1627 0.1473 0.068 Uiso 1 1 calc R . . H17A H 0.5656 0.0564 0.4171 0.068 Uiso 1 1 calc R . . H17B H 0.4319 0.0676 0.3931 0.068 Uiso 1 1 calc R . . H18A H 0.4557 0.2563 0.3816 0.075 Uiso 1 1 calc R . . H18B H 0.5028 0.2167 0.4657 0.075 Uiso 1 1 calc R . . H20 H 0.8262 0.3008 0.4366 0.071 Uiso 1 1 calc R . . H21 H 0.9037 0.4682 0.4647 0.073 Uiso 1 1 calc R . . H23 H 0.5903 0.5876 0.4508 0.078 Uiso 1 1 calc R . . H24 H 0.5124 0.4190 0.4269 0.071 Uiso 1 1 calc R . . Cl1 Cl 0.63576(7) 0.25293(6) 0.15940(4) 0.0764(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0443(16) 0.0507(18) 0.0811(17) -0.0119(14) 0.0099(14) -0.0055(13) C2 0.0416(16) 0.0517(18) 0.0873(18) -0.0050(14) 0.0077(14) -0.0020(14) C3 0.0336(16) 0.065(2) 0.0520(15) -0.0063(14) 0.0087(13) 0.0007(16) C4 0.0496(19) 0.069(2) 0.0713(17) -0.0012(14) 0.0161(15) -0.0077(16) C5 0.050(2) 0.092(3) 0.0727(19) -0.0141(17) 0.0228(16) -0.0171(18) C6 0.0366(19) 0.109(3) 0.0508(17) -0.0146(17) 0.0059(14) 0.008(2) C7 0.054(2) 0.094(2) 0.0583(17) 0.0005(15) 0.0089(15) 0.0169(19) C8 0.0467(18) 0.069(2) 0.0677(16) 0.0022(14) 0.0105(14) 0.0016(15) C9 0.0402(15) 0.0541(17) 0.0632(15) -0.0008(12) -0.0014(13) 0.0002(13) C10 0.0365(15) 0.0610(18) 0.0722(16) -0.0008(13) -0.0049(13) 0.0011(14) C12 0.0411(17) 0.0599(19) 0.0647(16) 0.0048(14) 0.0033(13) 0.0069(15) C11 0.0399(17) 0.0571(19) 0.0549(15) -0.0077(13) 0.0073(13) -0.0036(15) C13 0.0468(17) 0.0548(18) 0.0748(17) 0.0033(13) 0.0140(15) -0.0045(16) C14 0.0335(17) 0.063(2) 0.0563(15) -0.0068(13) 0.0102(13) -0.0047(15) C15 0.0397(17) 0.066(2) 0.0573(15) -0.0016(14) 0.0018(13) 0.0099(15) C16 0.0428(16) 0.0552(18) 0.0665(16) 0.0040(13) 0.0012(14) 0.0039(15) C17 0.0415(16) 0.0624(19) 0.0640(17) 0.0042(14) 0.0061(12) -0.0116(13) C18 0.0412(17) 0.077(2) 0.0685(16) -0.0133(14) 0.0095(13) -0.0091(15) C19 0.0484(19) 0.0517(19) 0.0574(15) -0.0029(13) 0.0074(14) -0.0098(16) C20 0.0454(18) 0.0523(19) 0.0762(17) 0.0013(13) 0.0084(14) -0.0006(14) C21 0.0481(17) 0.066(2) 0.0624(16) 0.0050(15) 0.0020(14) -0.0080(17) C22 0.068(2) 0.048(2) 0.0593(16) 0.0026(13) 0.0119(15) -0.0059(18) C23 0.069(2) 0.057(2) 0.0674(17) 0.0002(14) 0.0153(16) 0.0104(17) C24 0.0425(17) 0.067(2) 0.0665(16) -0.0039(14) 0.0096(13) 0.0035(17) N1 0.0395(13) 0.0498(15) 0.0622(14) -0.0024(11) 0.0074(11) -0.0080(12) N2 0.055(2) 0.157(4) 0.0688(19) -0.0202(19) 0.0131(17) 0.024(2) N3 0.0495(18) 0.081(2) 0.0819(17) -0.0066(15) 0.0149(14) -0.0054(17) N4 0.100(2) 0.061(2) 0.1026(19) -0.0047(16) 0.0311(19) -0.010(2) O1 0.0366(10) 0.0586(12) 0.0832(11) 0.0080(9) 0.0045(9) -0.0073(9) O2 0.0639(15) 0.211(3) 0.0927(17) 0.0009(16) -0.0023(13) 0.0341(16) O3 0.0515(15) 0.187(3) 0.158(2) -0.0439(18) 0.0282(14) -0.0294(15) O4 0.0388(10) 0.0626(12) 0.0745(11) 0.0008(9) -0.0006(9) -0.0021(9) O5 0.0708(15) 0.1050(19) 0.192(2) 0.0428(17) 0.0193(14) -0.0237(14) O6 0.0412(12) 0.1163(18) 0.1355(17) 0.0033(13) -0.0025(12) -0.0032(12) O7 0.0465(11) 0.0619(13) 0.0941(12) -0.0128(9) 0.0168(9) -0.0093(10) O8 0.141(2) 0.0526(16) 0.245(3) -0.0104(17) 0.058(2) -0.0037(15) O9 0.0957(17) 0.0812(16) 0.1316(17) -0.0128(12) 0.0107(15) -0.0343(15) O10 0.232(3) 0.146(2) 0.0908(15) 0.0251(14) 0.0378(16) 0.104(2) O11 0.1262(18) 0.1027(18) 0.1688(19) -0.0694(15) 0.0283(15) -0.0460(15) O12 0.1314(17) 0.0729(14) 0.0791(12) 0.0055(10) 0.0308(12) -0.0037(12) O13 0.0893(17) 0.138(2) 0.209(2) -0.0595(17) 0.0588(16) -0.0427(15) Cl1 0.0737(6) 0.0632(6) 0.0912(6) -0.0090(5) 0.0165(5) -0.0042(5) _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 Cl1 O10 1.3919(19) . ? Cl1 O11 1.3959(18) . ? Cl1 O13 1.3996(19) . ? Cl1 O12 1.4357(16) . ? N1 C17 1.504(2) . ? N1 C9 1.504(2) . ? N1 C1 1.513(2) . ? C3 O1 1.357(2) . ? C3 C4 1.380(3) . ? C3 C8 1.389(3) . ? C4 C5 1.377(3) . ? C2 O1 1.412(2) . ? C2 C1 1.502(3) . ? C5 C6 1.380(3) . ? C6 C7 1.356(3) . ? C6 N2 1.467(3) . ? C8 C7 1.378(3) . ? O3 N2 1.196(3) . ? O2 N2 1.234(3) . ? C11 O4 1.376(2) . ? C11 C12 1.381(3) . ? C11 C16 1.389(3) . ? C10 O4 1.421(2) . ? C10 C9 1.520(3) . ? C16 C15 1.381(3) . ? C14 C13 1.365(3) . ? C14 C15 1.370(3) . ? C14 N3 1.453(3) . ? C12 C13 1.376(3) . ? O6 N3 1.205(2) . ? O5 N3 1.214(2) . ? C17 C18 1.516(3) . ? C21 C22 1.375(3) . ? C21 C20 1.370(3) . ? C19 O7 1.369(2) . ? C19 C20 1.378(3) . ? C19 C24 1.381(3) . ? C22 C23 1.371(3) . ? C22 N4 1.463(3) . ? C18 O7 1.426(2) . ? C23 C24 1.375(3) . ? O9 N4 1.211(3) . ? O8 N4 1.223(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 O10 Cl1 O11 111.72(15) . . ? O10 Cl1 O13 109.06(16) . . ? O11 Cl1 O13 108.65(13) . . ? O10 Cl1 O12 108.51(12) . . ? O11 Cl1 O12 110.29(12) . . ? O13 Cl1 O12 108.56(14) . . ? C17 N1 C9 112.63(17) . . ? C17 N1 C1 114.41(18) . . ? C9 N1 C1 110.16(16) . . ? O1 C3 C4 115.1(2) . . ? O1 C3 C8 124.4(2) . . ? C4 C3 C8 120.5(2) . . ? C3 C4 C5 120.0(2) . . ? O1 C2 C1 106.67(18) . . ? C4 C5 C6 118.5(3) . . ? C7 C6 C5 122.3(3) . . ? C7 C6 N2 120.5(3) . . ? C5 C6 N2 117.2(3) . . ? C2 C1 N1 113.99(17) . . ? C7 C8 C3 119.2(2) . . ? C6 C7 C8 119.6(3) . . ? C3 O1 C2 118.38(18) . . ? O3 N2 O2 124.0(3) . . ? O3 N2 C6 119.8(3) . . ? O2 N2 C6 116.2(3) . . ? O4 C11 C12 123.2(2) . . ? O4 C11 C16 115.8(2) . . ? C12 C11 C16 120.9(2) . . ? O4 C10 C9 105.70(18) . . ? C15 C16 C11 119.2(2) . . ? C13 C14 C15 122.3(2) . . ? C13 C14 N3 119.0(3) . . ? C15 C14 N3 118.7(2) . . ? C14 C15 C16 118.9(2) . . ? C13 C12 C11 119.2(2) . . ? N1 C9 C10 112.69(18) . . ? C14 C13 C12 119.4(2) . . ? C11 O4 C10 116.75(18) . . ? O6 N3 O5 121.8(3) . . ? O6 N3 C14 119.7(3) . . ? O5 N3 C14 118.5(3) . . ? N1 C17 C18 111.08(18) . . ? C22 C21 C20 119.1(2) . . ? O7 C19 C20 114.4(2) . . ? O7 C19 C24 124.1(2) . . ? C20 C19 C24 121.5(2) . . ? C21 C22 C23 121.9(3) . . ? C21 C22 N4 118.5(3) . . ? C23 C22 N4 119.6(3) . . ? C21 C20 C19 119.3(2) . . ? O7 C18 C17 104.29(18) . . ? C22 C23 C24 119.3(2) . . ? C23 C24 C19 118.9(2) . . ? C19 O7 C18 120.37(18) . . ? O9 N4 O8 123.6(3) . . ? O9 N4 C22 119.8(3) . . ? O8 N4 C22 116.5(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.317 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.037 data_nitro-CF3COOH _database_code_depnum_ccdc_archive 'CCDC 761165' #TrackingRef '- CCDC 761161-66.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H25 N4 O9, C2 F3 O2' _chemical_formula_sum 'C26 H25 F3 N4 O11 ' _chemical_formula_weight 626.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8340(9) _cell_length_b 12.5542(11) _cell_length_c 16.8656(18) _cell_angle_alpha 99.533(5) _cell_angle_beta 94.301(6) _cell_angle_gamma 99.636(7) _cell_volume 1399.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1183 _cell_measurement_theta_min 3.43 _cell_measurement_theta_max 21.66 _exptl_crystal_description rectangular _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9501 _exptl_absorpt_correction_T_max 0.9684 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10145 _diffrn_reflns_av_R_equivalents 0.101 _diffrn_reflns_av_sigmaI/netI 0.1632 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.37 _reflns_number_total 7010 _reflns_number_gt 6711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_number_reflns 6017 _refine_ls_number_parameters 402 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1700 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4439(6) 0.1577(3) 0.1507(2) 0.0524(11) Uani 1 1 d . . . C2 C 0.5091(6) 0.1896(3) 0.0723(2) 0.0556(11) Uani 1 1 d . . . C3 C 0.6377(6) 0.3567(3) 0.0270(2) 0.0417(9) Uani 1 1 d . . . C4 C 0.6054(6) 0.3058(3) -0.0532(2) 0.0497(10) Uani 1 1 d . . . C5 C 0.6608(6) 0.3661(3) -0.1125(2) 0.0598(12) Uani 1 1 d . . . C6 C 0.7434(6) 0.4751(3) -0.0904(2) 0.0524(11) Uani 1 1 d . . . C7 C 0.7759(5) 0.5269(3) -0.0106(2) 0.0489(10) Uani 1 1 d . . . C8 C 0.7198(5) 0.4685(3) 0.0474(2) 0.0461(10) Uani 1 1 d . . . C9 C 0.7884(5) 0.2259(2) 0.22510(19) 0.0407(9) Uani 1 1 d . . . C10 C 0.7551(6) 0.3338(2) 0.27177(19) 0.0449(10) Uani 1 1 d . . . C11 C 0.7504(5) 0.4180(2) 0.4097(2) 0.0394(9) Uani 1 1 d . . . C12 C 0.7453(5) 0.5206(2) 0.3910(2) 0.0435(10) Uani 1 1 d . . . C13 C 0.7471(5) 0.6084(3) 0.4524(2) 0.0492(10) Uani 1 1 d . . . C14 C 0.7497(5) 0.5928(3) 0.5306(2) 0.0408(9) Uani 1 1 d . . . C15 C 0.7538(5) 0.4908(3) 0.5508(2) 0.0436(9) Uani 1 1 d . . . C16 C 0.7552(5) 0.4029(3) 0.4899(2) 0.0441(10) Uani 1 1 d . . . C17 C 0.5151(6) 0.1026(3) 0.2792(2) 0.0469(10) Uani 1 1 d . . . C18 C 0.6589(6) 0.0657(3) 0.3373(2) 0.0552(11) Uani 1 1 d . . . C19 C 0.8486(6) -0.0778(3) 0.3289(2) 0.0503(10) Uani 1 1 d . . . C20 C 0.9977(6) -0.0195(3) 0.3910(2) 0.0571(11) Uani 1 1 d . . . C21 C 1.1618(7) -0.0604(3) 0.4101(2) 0.0598(12) Uani 1 1 d . . . C22 C 1.1899(6) -0.1604(3) 0.3666(2) 0.0555(11) Uani 1 1 d . . . C23 C 1.0465(6) -0.2196(3) 0.3065(2) 0.0611(12) Uani 1 1 d . . . C24 C 0.8766(7) -0.1801(3) 0.2886(2) 0.0621(12) Uani 1 1 d . . . C25 C 0.9983(8) 0.8804(4) 0.0880(3) 0.0733(14) Uani 1 1 d . . . C26 C 0.9032(7) 0.9703(3) 0.1325(3) 0.0540(11) Uani 1 1 d . . . N1 N 0.6084(4) 0.1356(2) 0.20664(16) 0.0385(7) Uani 1 1 d . . . N2 N 0.8116(7) 0.5378(3) -0.1518(2) 0.0846(13) Uani 1 1 d . . . N3 N 0.7514(5) 0.6853(3) 0.5958(2) 0.0594(9) Uani 1 1 d . . . N4 N 1.3754(6) -0.1996(3) 0.3847(2) 0.0675(10) Uani 1 1 d . . . O1 O 0.5881(4) 0.30644(18) 0.08910(14) 0.0533(7) Uani 1 1 d . . . O2 O 0.8667(5) 0.6355(2) -0.13344(19) 0.0901(11) Uani 1 1 d . . . O3 O 0.8200(8) 0.4871(3) -0.2184(2) 0.159(2) Uani 1 1 d . . . O4 O 0.7561(4) 0.32581(16) 0.35488(13) 0.0486(7) Uani 1 1 d . . . O5 O 0.7337(5) 0.6689(2) 0.66424(18) 0.0803(10) Uani 1 1 d . . . O6 O 0.7655(6) 0.7761(2) 0.57828(19) 0.1025(13) Uani 1 1 d . . . O7 O 0.6857(4) -0.04296(18) 0.30262(15) 0.0553(7) Uani 1 1 d . . . O8 O 1.4052(5) -0.2807(3) 0.3401(2) 0.0947(11) Uani 1 1 d . . . O9 O 1.4923(5) -0.1482(3) 0.4424(2) 0.0915(11) Uani 1 1 d . . . O10 O 1.0152(4) 1.0375(2) 0.18344(17) 0.0693(9) Uani 1 1 d . . . O11 O 0.7222(5) 0.9619(2) 0.11173(16) 0.0603(8) Uani 1 1 d . . . F1 F 0.9093(5) 0.7810(2) 0.09113(18) 0.1147(11) Uani 1 1 d . . . F2 F 1.1849(5) 0.8874(3) 0.1130(3) 0.195(2) Uani 1 1 d . . . F3 F 0.9955(6) 0.8792(3) 0.0100(2) 0.1529(17) Uani 1 1 d . . . H1N H 0.647(5) 0.067(2) 0.1735(17) 0.048(10) Uiso 1 1 d . . . H1A H 0.3853 0.2163 0.1790 0.063 Uiso 1 1 calc R . . H1B H 0.3407 0.0924 0.1376 0.063 Uiso 1 1 calc R . . H2A H 0.6106 0.1491 0.0533 0.067 Uiso 1 1 calc R . . H2B H 0.3963 0.1730 0.0310 0.067 Uiso 1 1 calc R . . H4 H 0.5472 0.2319 -0.0673 0.060 Uiso 1 1 calc R . . H5 H 0.6418 0.3327 -0.1667 0.072 Uiso 1 1 calc R . . H7 H 0.8353 0.6007 0.0032 0.059 Uiso 1 1 calc R . . H8 H 0.7362 0.5033 0.1012 0.055 Uiso 1 1 calc R . . H9A H 0.8378 0.2389 0.1745 0.049 Uiso 1 1 calc R . . H9B H 0.8919 0.2007 0.2557 0.049 Uiso 1 1 calc R . . H10A H 0.8600 0.3929 0.2648 0.054 Uiso 1 1 calc R . . H10B H 0.6281 0.3495 0.2519 0.054 Uiso 1 1 calc R . . H12 H 0.7406 0.5304 0.3375 0.052 Uiso 1 1 calc R . . H13 H 0.7466 0.6781 0.4405 0.059 Uiso 1 1 calc R . . H15 H 0.7556 0.4816 0.6045 0.052 Uiso 1 1 calc R . . H16 H 0.7594 0.3338 0.5022 0.053 Uiso 1 1 calc R . . H17A H 0.4023 0.0432 0.2608 0.056 Uiso 1 1 calc R . . H17B H 0.4650 0.1644 0.3077 0.056 Uiso 1 1 calc R . . H18A H 0.7859 0.1160 0.3461 0.066 Uiso 1 1 calc R . . H18B H 0.6055 0.0650 0.3889 0.066 Uiso 1 1 calc R . . H20 H 0.9821 0.0482 0.4192 0.069 Uiso 1 1 calc R . . H21 H 1.2562 -0.0220 0.4521 0.072 Uiso 1 1 calc R . . H23 H 1.0652 -0.2865 0.2779 0.073 Uiso 1 1 calc R . . H24 H 0.7784 -0.2218 0.2493 0.075 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 C1 0.044(3) 0.049(2) 0.064(3) 0.0188(19) -0.005(2) 0.0029(19) C2 0.064(3) 0.045(2) 0.052(3) 0.0091(18) -0.004(2) 0.001(2) C3 0.033(3) 0.046(2) 0.049(2) 0.0102(18) -0.0023(17) 0.0171(17) C4 0.055(3) 0.0363(19) 0.058(3) 0.0035(18) 0.013(2) 0.0128(18) C5 0.081(4) 0.050(2) 0.050(3) 0.0079(19) 0.010(2) 0.016(2) C6 0.055(3) 0.043(2) 0.064(3) 0.0200(19) 0.012(2) 0.0105(19) C7 0.036(3) 0.037(2) 0.076(3) 0.015(2) 0.001(2) 0.0096(17) C8 0.038(3) 0.040(2) 0.054(2) -0.0025(17) -0.0086(19) 0.0066(18) C9 0.034(3) 0.0403(19) 0.047(2) 0.0045(16) 0.0044(17) 0.0078(17) C10 0.051(3) 0.0356(19) 0.049(2) 0.0068(16) 0.0053(18) 0.0096(17) C11 0.033(3) 0.0349(18) 0.051(2) 0.0046(16) 0.0043(17) 0.0104(16) C12 0.048(3) 0.041(2) 0.042(2) 0.0073(16) -0.0046(18) 0.0151(18) C13 0.047(3) 0.039(2) 0.062(3) 0.0055(18) -0.005(2) 0.0163(18) C14 0.026(2) 0.041(2) 0.053(2) -0.0032(17) -0.0001(17) 0.0131(16) C15 0.032(3) 0.050(2) 0.049(2) 0.0069(17) 0.0028(18) 0.0090(18) C16 0.045(3) 0.042(2) 0.046(2) 0.0106(16) 0.0041(18) 0.0101(18) C17 0.044(3) 0.042(2) 0.060(3) 0.0095(17) 0.020(2) 0.0177(18) C18 0.076(4) 0.044(2) 0.051(2) 0.0081(17) 0.013(2) 0.024(2) C19 0.050(3) 0.047(2) 0.059(3) 0.0174(19) 0.007(2) 0.012(2) C20 0.068(4) 0.053(2) 0.053(3) 0.0121(19) 0.000(2) 0.018(2) C21 0.067(4) 0.060(3) 0.052(3) 0.0081(19) -0.006(2) 0.017(2) C22 0.054(3) 0.053(2) 0.066(3) 0.025(2) 0.008(2) 0.015(2) C23 0.065(4) 0.045(2) 0.077(3) 0.013(2) 0.008(2) 0.018(2) C24 0.070(4) 0.039(2) 0.074(3) 0.0036(19) -0.005(2) 0.011(2) C25 0.062(4) 0.059(3) 0.092(4) -0.007(3) 0.010(3) 0.010(3) C26 0.054(3) 0.040(2) 0.070(3) 0.0073(19) 0.016(2) 0.010(2) N1 0.036(2) 0.0339(15) 0.0487(19) 0.0094(13) 0.0100(15) 0.0103(14) N2 0.109(4) 0.066(3) 0.080(3) 0.023(2) 0.017(3) 0.008(3) N3 0.049(3) 0.051(2) 0.073(3) -0.0054(19) -0.0051(19) 0.0155(17) N4 0.061(3) 0.075(3) 0.080(3) 0.042(2) 0.008(2) 0.022(2) O1 0.065(2) 0.0425(14) 0.0513(16) 0.0098(12) 0.0048(14) 0.0055(13) O2 0.100(3) 0.062(2) 0.119(3) 0.0427(18) 0.022(2) 0.0132(19) O3 0.291(7) 0.095(3) 0.080(3) 0.029(2) 0.038(3) -0.014(3) O4 0.065(2) 0.0375(13) 0.0458(15) 0.0059(11) 0.0119(13) 0.0162(13) O5 0.096(3) 0.081(2) 0.059(2) -0.0084(17) 0.0009(18) 0.0274(19) O6 0.157(4) 0.0482(18) 0.095(3) -0.0071(17) 0.006(2) 0.021(2) O7 0.062(2) 0.0423(14) 0.0628(17) 0.0098(12) -0.0055(14) 0.0194(14) O8 0.099(3) 0.079(2) 0.119(3) 0.0238(19) 0.007(2) 0.050(2) O9 0.089(3) 0.099(3) 0.088(3) 0.0287(19) -0.018(2) 0.024(2) O10 0.056(2) 0.0507(16) 0.091(2) -0.0126(15) 0.0091(16) 0.0057(14) O11 0.050(2) 0.0590(17) 0.0673(19) -0.0031(13) 0.0004(15) 0.0150(15) F1 0.133(3) 0.0492(16) 0.153(3) -0.0158(16) 0.027(2) 0.0193(17) F2 0.076(3) 0.113(3) 0.344(6) -0.117(3) -0.023(3) 0.046(2) F3 0.231(5) 0.137(3) 0.122(3) 0.018(2) 0.100(3) 0.091(3) _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 C9 1.501(4) . ? N1 C1 1.504(5) . ? N1 C17 1.507(4) . ? C3 O1 1.345(4) . ? C3 C4 1.381(4) . ? C3 C8 1.397(4) . ? C4 C5 1.389(5) . ? C6 C5 1.368(4) . ? C6 C7 1.378(5) . ? C6 N2 1.459(5) . ? C1 C2 1.520(5) . ? C8 C7 1.357(5) . ? C2 O1 1.449(4) . ? O2 N2 1.203(4) . ? O3 N2 1.207(4) . ? C12 C13 1.379(4) . ? C12 C11 1.382(4) . ? C16 C15 1.379(4) . ? C16 C11 1.395(4) . ? C11 O4 1.365(3) . ? C10 O4 1.421(4) . ? C10 C9 1.511(4) . ? C13 C14 1.365(5) . ? C14 C15 1.384(5) . ? C14 N3 1.459(4) . ? O5 N3 1.217(4) . ? O6 N3 1.213(4) . ? C19 O7 1.334(5) . ? C19 C24 1.400(5) . ? C19 C20 1.417(5) . ? C22 C23 1.377(5) . ? C22 C21 1.395(5) . ? C22 N4 1.465(5) . ? C17 C18 1.516(5) . ? C24 C23 1.369(5) . ? C18 O7 1.440(4) . ? C20 C21 1.348(5) . ? O9 N4 1.226(4) . ? O8 N4 1.217(4) . ? C25 F2 1.297(6) . ? C25 F1 1.305(5) . ? C25 F3 1.312(6) . ? C25 C26 1.516(5) . ? C26 O10 1.217(4) . ? C26 O11 1.243(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C1 114.3(3) . . ? C9 N1 C17 115.5(3) . . ? C1 N1 C17 107.0(3) . . ? O1 C3 C4 124.2(3) . . ? O1 C3 C8 115.9(3) . . ? C4 C3 C8 119.8(3) . . ? C3 C4 C5 119.4(3) . . ? C5 C6 C7 121.9(3) . . ? C5 C6 N2 119.7(4) . . ? C7 C6 N2 118.2(3) . . ? N1 C1 C2 114.7(3) . . ? C7 C8 C3 120.7(3) . . ? C6 C5 C4 119.3(3) . . ? C8 C7 C6 118.9(3) . . ? O1 C2 C1 107.3(3) . . ? C3 O1 C2 118.6(3) . . ? O2 N2 O3 122.8(4) . . ? O2 N2 C6 119.5(4) . . ? O3 N2 C6 117.5(4) . . ? C13 C12 C11 119.5(3) . . ? C15 C16 C11 119.9(3) . . ? O4 C11 C12 125.0(3) . . ? O4 C11 C16 114.7(3) . . ? C12 C11 C16 120.4(3) . . ? O4 C10 C9 108.5(3) . . ? N1 C9 C10 115.6(3) . . ? C14 C13 C12 119.8(3) . . ? C13 C14 C15 121.8(3) . . ? C13 C14 N3 120.1(3) . . ? C15 C14 N3 118.1(3) . . ? C16 C15 C14 118.7(3) . . ? C11 O4 C10 118.6(2) . . ? O6 N3 O5 122.8(3) . . ? O6 N3 C14 117.6(4) . . ? O5 N3 C14 119.6(3) . . ? O7 C19 C24 116.2(4) . . ? O7 C19 C20 126.2(3) . . ? C24 C19 C20 117.6(4) . . ? C23 C22 C21 120.2(4) . . ? C23 C22 N4 120.9(4) . . ? C21 C22 N4 118.9(4) . . ? N1 C17 C18 113.2(3) . . ? C23 C24 C19 120.9(4) . . ? O7 C18 C17 108.2(3) . . ? C24 C23 C22 120.1(4) . . ? C21 C20 C19 121.3(4) . . ? C20 C21 C22 119.9(4) . . ? C19 O7 C18 118.3(3) . . ? O8 N4 O9 124.1(4) . . ? O8 N4 C22 117.3(4) . . ? O9 N4 C22 118.5(4) . . ? F2 C25 F1 106.7(5) . . ? F2 C25 F3 104.7(5) . . ? F1 C25 F3 102.7(4) . . ? F2 C25 C26 113.5(4) . . ? F1 C25 C26 114.2(4) . . ? F3 C25 C26 114.0(5) . . ? O10 C26 O11 130.7(4) . . ? O10 C26 C25 115.0(4) . . ? O11 C26 C25 114.3(4) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.382 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.056 data_nitro-SiF6 _database_code_depnum_ccdc_archive 'CCDC 761166' #TrackingRef '- CCDC 761161-66.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H50 F6 N8 O20 Si' _chemical_formula_weight 1201.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 15.4544(9) _cell_length_b 17.9320(9) _cell_length_c 18.6070(10) _cell_angle_alpha 116.352(3) _cell_angle_beta 94.269(5) _cell_angle_gamma 106.342(3) _cell_volume 4313.2(4) _cell_formula_units_Z 3 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5889 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 21.45 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1866 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.941 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45963 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0936 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 30.07 _reflns_number_total 24200 _reflns_number_gt 19542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1238P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_number_reflns 24200 _refine_ls_number_parameters 1121 _refine_ls_number_restraints 1779 _refine_ls_R_factor_all 0.1594 _refine_ls_R_factor_gt 0.0935 _refine_ls_wR_factor_ref 0.2440 _refine_ls_wR_factor_gt 0.2127 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.126 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.67054(7) 0.67049(6) 0.66660(6) 0.0481(3) Uani 1 1 d U . . F1 F 0.64387(17) 0.59204(15) 0.69461(15) 0.0751(7) Uani 1 1 d U . . F4 F 0.69748(15) 0.74910(14) 0.63831(14) 0.0647(6) Uani 1 1 d U . . F2 F 0.74144(18) 0.74266(14) 0.76141(13) 0.0829(8) Uani 1 1 d U . . F6 F 0.59982(16) 0.59857(14) 0.57149(13) 0.0683(7) Uani 1 1 d U . . F3 F 0.75772(17) 0.63960(17) 0.63410(15) 0.0778(7) Uani 1 1 d U . . F5 F 0.58235(18) 0.70157(17) 0.69884(15) 0.0785(7) Uani 1 1 d U . . N1 N 0.8314(2) 0.6612(2) 0.81937(18) 0.0425(7) Uani 1 1 d U . . C3 C 0.8975(2) 0.4614(2) 0.86203(19) 0.0369(8) Uani 1 1 d U . . C1 C 0.8209(3) 0.5689(2) 0.75392(19) 0.0460(9) Uani 1 1 d U . . H1A H 0.7568 0.5308 0.7402 0.055 Uiso 1 1 calc R . . H1B H 0.8339 0.5715 0.7047 0.055 Uiso 1 1 calc R . . C8 C 0.8652(3) 0.4405(2) 0.9211(2) 0.0453(9) Uani 1 1 d U . . H8 H 0.8157 0.4555 0.9411 0.054 Uiso 1 1 calc R . . C6 C 0.9814(3) 0.3772(2) 0.9200(2) 0.0481(9) Uani 1 1 d U . . C2 C 0.8817(3) 0.5264(2) 0.7764(2) 0.0471(9) Uani 1 1 d U . . H2A H 0.8808 0.4743 0.7274 0.057 Uiso 1 1 calc R . . H2B H 0.9450 0.5679 0.7994 0.057 Uiso 1 1 calc R . . C4 C 0.9711(2) 0.4407(2) 0.8334(2) 0.0417(8) Uani 1 1 d U . . H4 H 0.9927 0.4547 0.7940 0.050 Uiso 1 1 calc R . . C7 C 0.9072(3) 0.3976(2) 0.9497(2) 0.0485(9) Uani 1 1 d U . . H7 H 0.8858 0.3825 0.9886 0.058 Uiso 1 1 calc R . . C5 C 1.0128(3) 0.3988(2) 0.8639(2) 0.0480(9) Uani 1 1 d U . . H5 H 1.0636 0.3853 0.8453 0.058 Uiso 1 1 calc R . . O1 O 0.84925(16) 0.50148(15) 0.83542(13) 0.0442(6) Uani 1 1 d U . . O3 O 0.9926(3) 0.3099(2) 0.9994(2) 0.0919(11) Uani 1 1 d U . . O2 O 1.0997(3) 0.3261(3) 0.9334(2) 0.1128(14) Uani 1 1 d U . . N2 N 1.0272(3) 0.3341(2) 0.9529(2) 0.0692(11) Uani 1 1 d U . . C9 C 0.9272(3) 0.7278(2) 0.8509(2) 0.0481(9) Uani 1 1 d U . . H9A H 0.9255 0.7848 0.8907 0.058 Uiso 1 1 calc R . . H9B H 0.9654 0.7102 0.8796 0.058 Uiso 1 1 calc R . . C16 C 1.0551(3) 0.5811(3) 0.6340(2) 0.0606(11) Uani 1 1 d U . . H16 H 1.0342 0.5352 0.6464 0.073 Uiso 1 1 calc R . . C15 C 1.0964(3) 0.5688(3) 0.5678(2) 0.0652(12) Uani 1 1 d U . . H15 H 1.1032 0.5147 0.5351 0.078 Uiso 1 1 calc R . . C10 C 0.9723(3) 0.7392(3) 0.7863(2) 0.0602(11) Uani 1 1 d U . . H10A H 0.9282 0.7402 0.7471 0.072 Uiso 1 1 calc R . . H10B H 1.0242 0.7951 0.8116 0.072 Uiso 1 1 calc R . . C11 C 1.0452(3) 0.6617(3) 0.6813(2) 0.0558(10) Uani 1 1 d U . . C14 C 1.1270(3) 0.6386(4) 0.5519(2) 0.0677(13) Uani 1 1 d U . . C13 C 1.1203(3) 0.7198(4) 0.6001(3) 0.0737(13) Uani 1 1 d U . . H13 H 1.1433 0.7663 0.5888 0.088 Uiso 1 1 calc R . . C12 C 1.0793(3) 0.7316(3) 0.6649(3) 0.0673(12) Uani 1 1 d U . . H12 H 1.0742 0.7864 0.6981 0.081 Uiso 1 1 calc R . . O4 O 1.00411(19) 0.66696(18) 0.74495(16) 0.0608(8) Uani 1 1 d U . . O6 O 1.1743(2) 0.5526(3) 0.4391(2) 0.1149(15) Uani 1 1 d U . . O5 O 1.1986(3) 0.6880(4) 0.4680(3) 0.1349(17) Uani 1 1 d U . . N3 N 1.1687(3) 0.6242(4) 0.4804(3) 0.0899(15) Uani 1 1 d U . . C17 C 0.7865(3) 0.6587(2) 0.8875(2) 0.0483(9) Uani 1 1 d U . . H17A H 0.8160 0.6320 0.9124 0.058 Uiso 1 1 calc R . . H17B H 0.7219 0.6208 0.8639 0.058 Uiso 1 1 calc R . . C18 C 0.7918(3) 0.7486(2) 0.9540(2) 0.0552(10) Uani 1 1 d U . . H18A H 0.8540 0.7829 0.9886 0.066 Uiso 1 1 calc R . . H18B H 0.7734 0.7819 0.9303 0.066 Uiso 1 1 calc R . . C19 C 0.7317(3) 0.7924(3) 1.0749(3) 0.0687(12) Uani 1 1 d U . . O7 O 0.7284(2) 0.72769(19) 0.99928(17) 0.0719(9) Uani 1 1 d U . . C21 C 0.7842(4) 0.9383(5) 1.1870(3) 0.138(3) Uani 1 1 d U . . H21 H 0.8228 0.9976 1.2118 0.166 Uiso 1 1 calc R . . C20 C 0.7899(3) 0.8788(4) 1.1106(3) 0.0915(17) Uani 1 1 d U . . H20 H 0.8326 0.8970 1.0837 0.110 Uiso 1 1 calc R . . C22 C 0.7231(4) 0.9115(6) 1.2263(3) 0.128(3) Uani 1 1 d U . . C24 C 0.6689(4) 0.7637(4) 1.1147(3) 0.0991(17) Uani 1 1 d U . . H24 H 0.6301 0.7046 1.0905 0.119 Uiso 1 1 calc R . . C23 C 0.6653(5) 0.8267(5) 1.1930(4) 0.123(2) Uani 1 1 d U . . H23 H 0.6236 0.8098 1.2212 0.147 Uiso 1 1 calc R . . O8 O 0.7517(4) 1.0517(6) 1.3297(4) 0.269(4) Uani 1 1 d U . . O9 O 0.6741(5) 0.9457(6) 1.3479(3) 0.257(4) Uani 1 1 d U . . N4 N 0.7155(5) 0.9736(7) 1.3070(4) 0.203(4) Uani 1 1 d U . . Si2 Si 1.0000 1.0000 1.0000 0.0414(4) Uani 1 2 d SU . . F9 F 0.97951(15) 0.92947(15) 1.03794(14) 0.0692(7) Uani 1 1 d U . . F8 F 0.9158(2) 0.92412(15) 0.91523(16) 0.0949(9) Uani 1 1 d U . . F7 F 1.0779(2) 0.9588(2) 0.95914(18) 0.0970(9) Uani 1 1 d U . . N5 N 0.1641(2) 0.99399(18) 0.15003(17) 0.0383(7) Uani 1 1 d U . . C25 C 0.2604(2) 1.0607(2) 0.1844(2) 0.0433(9) Uani 1 1 d U . . H25A H 0.2592 1.1158 0.2283 0.052 Uiso 1 1 calc R . . H25B H 0.2989 1.0393 0.2084 0.052 Uiso 1 1 calc R . . C26 C 0.3038(3) 1.0794(3) 0.1224(2) 0.0535(10) Uani 1 1 d U . . H26A H 0.2595 1.0855 0.0875 0.064 Uiso 1 1 calc R . . H26B H 0.3568 1.1345 0.1501 0.064 Uiso 1 1 calc R . . C27 C 0.3652(3) 1.0027(3) 0.0054(2) 0.0520(10) Uani 1 1 d U . . C32 C 0.3818(3) 0.9262(3) -0.0424(2) 0.0611(11) Uani 1 1 d U . . H32 H 0.3691 0.8808 -0.0289 0.073 Uiso 1 1 calc R . . C31 C 0.4175(3) 0.9168(3) -0.1109(2) 0.0729(13) Uani 1 1 d U . . H31 H 0.4307 0.8661 -0.1429 0.088 Uiso 1 1 calc R . . C28 C 0.3833(3) 1.0712(3) -0.0138(3) 0.0681(12) Uani 1 1 d U . . H28 H 0.3727 1.1231 0.0194 0.082 Uiso 1 1 calc R . . C30 C 0.4330(3) 0.9850(4) -0.1304(3) 0.0760(14) Uani 1 1 d U . . C29 C 0.4170(3) 1.0613(4) -0.0826(3) 0.0818(14) Uani 1 1 d U . . H29 H 0.4290 1.1063 -0.0966 0.098 Uiso 1 1 calc R . . C35 C 0.2372(2) 0.7968(2) 0.1915(2) 0.0399(8) Uani 1 1 d U . . C34 C 0.2181(2) 0.8610(2) 0.1054(2) 0.0437(9) Uani 1 1 d U . . H34A H 0.2151 0.8076 0.0566 0.052 Uiso 1 1 calc R . . H34B H 0.2815 0.9024 0.1254 0.052 Uiso 1 1 calc R . . C33 C 0.1550(2) 0.9017(2) 0.08439(19) 0.0420(8) Uani 1 1 d U . . H33A H 0.0916 0.8625 0.0716 0.050 Uiso 1 1 calc R . . H33B H 0.1660 0.9043 0.0348 0.050 Uiso 1 1 calc R . . C39 C 0.2454(3) 0.7309(2) 0.2777(2) 0.0495(9) Uani 1 1 d U . . H39 H 0.2242 0.7162 0.3169 0.059 Uiso 1 1 calc R . . C40 C 0.2054(3) 0.7749(2) 0.2508(2) 0.0441(9) Uani 1 1 d U . . H40 H 0.1567 0.7908 0.2717 0.053 Uiso 1 1 calc R . . C38 C 0.3172(3) 0.7084(2) 0.2467(2) 0.0547(10) Uani 1 1 d U . . C36 C 0.3100(3) 0.7753(2) 0.1615(2) 0.0505(9) Uani 1 1 d U . . H36 H 0.3319 0.7906 0.1229 0.061 Uiso 1 1 calc R . . C37 C 0.3508(3) 0.7302(3) 0.1897(2) 0.0572(10) Uani 1 1 d U . . H37 H 0.4004 0.7151 0.1701 0.069 Uiso 1 1 calc R . . O10 O 0.33302(18) 1.00583(17) 0.07298(15) 0.0552(7) Uani 1 1 d U . . O11 O 0.4824(4) 1.0362(4) -0.2197(3) 0.159(2) Uani 1 1 d U . . O12 O 0.4852(4) 0.9061(3) -0.2443(2) 0.150(2) Uani 1 1 d U . . N6 N 0.4692(4) 0.9741(5) -0.2036(3) 0.1115(18) Uani 1 1 d U . . O13 O 0.19053(17) 0.83936(16) 0.16774(14) 0.0480(6) Uani 1 1 d U . . O15 O 0.3303(2) 0.6409(2) 0.3256(2) 0.0908(11) Uani 1 1 d U . . O14 O 0.4253(4) 0.6450(4) 0.2504(3) 0.149(2) Uani 1 1 d U . . N7 N 0.3592(3) 0.6608(3) 0.2760(3) 0.0773(12) Uani 1 1 d U . . C41 C 0.1155(3) 0.9917(2) 0.2164(2) 0.0453(9) Uani 1 1 d U . . H41A H 0.0523 0.9501 0.1911 0.054 Uiso 1 1 calc R . . H41B H 0.1466 0.9706 0.2466 0.054 Uiso 1 1 calc R . . C42 C 0.1139(3) 1.0816(3) 0.2757(2) 0.0594(11) Uani 1 1 d U . . H42A H 0.1715 1.1167 0.3175 0.071 Uiso 1 1 calc R . . H42B H 0.1050 1.1135 0.2469 0.071 Uiso 1 1 calc R . . C45 C 0.0861(3) 1.2790(3) 0.4956(2) 0.0625(11) Uani 1 1 d U . . H45 H 0.1250 1.3382 0.5209 0.075 Uiso 1 1 calc R . . C44 C 0.0961(3) 1.2173(3) 0.4217(2) 0.0563(10) Uani 1 1 d U . . H44 H 0.1430 1.2340 0.3974 0.068 Uiso 1 1 calc R . . C43 C 0.0355(3) 1.1307(3) 0.3847(2) 0.0530(10) Uani 1 1 d U . . C46 C 0.0174(3) 1.2514(3) 0.5312(2) 0.0622(11) Uani 1 1 d U . . C48 C -0.0329(3) 1.1056(3) 0.4203(2) 0.0619(11) Uani 1 1 d U . . H48 H -0.0732 1.0469 0.3941 0.074 Uiso 1 1 calc R . . C47 C -0.0433(3) 1.1653(3) 0.4940(3) 0.0674(12) Uani 1 1 d U . . H47 H -0.0901 1.1480 0.5181 0.081 Uiso 1 1 calc R . . O16 O 0.03797(18) 1.06428(18) 0.31191(15) 0.0638(8) Uani 1 1 d U . . O17 O 0.0536(3) 1.3938(3) 0.6377(2) 0.1282(16) Uani 1 1 d U . . O18 O -0.0447(3) 1.2867(3) 0.6457(2) 0.1278(16) Uani 1 1 d U . . N8 N 0.0095(3) 1.3163(3) 0.6107(2) 0.0821(12) Uani 1 1 d U . . N9 N 0.5017(2) 0.66760(18) 0.50984(17) 0.0402(7) Uani 1 1 d U . . C51 C 0.4344(2) 0.8654(2) 0.46464(19) 0.0372(8) Uani 1 1 d U . . C54 C 0.3610(2) 0.9571(2) 0.4076(2) 0.0398(8) Uani 1 1 d U . . C56 C 0.4714(2) 0.8885(2) 0.40854(19) 0.0402(8) Uani 1 1 d U . . H56 H 0.5210 0.8724 0.3900 0.048 Uiso 1 1 calc R . . C52 C 0.3598(2) 0.8883(2) 0.4920(2) 0.0414(8) Uani 1 1 d U . . H52 H 0.3350 0.8730 0.5296 0.050 Uiso 1 1 calc R . . C49 C 0.5087(2) 0.7601(2) 0.5743(2) 0.0434(8) Uani 1 1 d U . . H49A H 0.4963 0.7580 0.6238 0.052 Uiso 1 1 calc R . . H49B H 0.5720 0.8000 0.5881 0.052 Uiso 1 1 calc R . . C50 C 0.4452(2) 0.7991(2) 0.5502(2) 0.0419(8) Uani 1 1 d U . . H50A H 0.3826 0.7559 0.5266 0.050 Uiso 1 1 calc R . . H50B H 0.4442 0.8511 0.5983 0.050 Uiso 1 1 calc R . . C55 C 0.4350(2) 0.9352(2) 0.38010(19) 0.0432(9) Uani 1 1 d U . . H55 H 0.4602 0.9515 0.3431 0.052 Uiso 1 1 calc R . . C53 C 0.3229(2) 0.9339(2) 0.4628(2) 0.0444(9) Uani 1 1 d U . . H53 H 0.2725 0.9491 0.4802 0.053 Uiso 1 1 calc R . . O19 O 0.47810(16) 0.82304(15) 0.49118(14) 0.0433(6) Uani 1 1 d U . . O20 O 0.3545(2) 1.0219(2) 0.3263(2) 0.0796(9) Uani 1 1 d U . . O21 O 0.2616(3) 1.0307(2) 0.4053(2) 0.0939(11) Uani 1 1 d U . . N10 N 0.3233(3) 1.0063(2) 0.3779(2) 0.0573(9) Uani 1 1 d U . . C57 C 0.4068(2) 0.5982(2) 0.4807(2) 0.0465(9) Uani 1 1 d U . . H57A H 0.3630 0.6197 0.4632 0.056 Uiso 1 1 calc R . . H57B H 0.4064 0.5452 0.4328 0.056 Uiso 1 1 calc R . . C58 C 0.3742(3) 0.5730(3) 0.5431(2) 0.0555(10) Uani 1 1 d U . . H58A H 0.3222 0.5172 0.5160 0.067 Uiso 1 1 calc R . . H58B H 0.4237 0.5655 0.5714 0.067 Uiso 1 1 calc R . . O22 O 0.34637(17) 0.64240(17) 0.60181(15) 0.0541(7) Uani 1 1 d U . . C59 C 0.3151(3) 0.6303(3) 0.6641(3) 0.0624(11) Uani 1 1 d U . . C63 C 0.2588(3) 0.6934(5) 0.7856(3) 0.103(2) Uani 1 1 d U . . H63 H 0.2447 0.7402 0.8247 0.124 Uiso 1 1 calc R . . C62 C 0.2458(4) 0.6185(6) 0.7899(4) 0.114(2) Uani 1 1 d U . . C60 C 0.2994(3) 0.5533(4) 0.6693(3) 0.0913(16) Uani 1 1 d U . . H60 H 0.3110 0.5052 0.6294 0.110 Uiso 1 1 calc R . . C61 C 0.2657(4) 0.5490(5) 0.7353(4) 0.111(2) Uani 1 1 d U . . H61 H 0.2571 0.4990 0.7416 0.133 Uiso 1 1 calc R . . C65 C 0.5365(3) 0.6625(3) 0.4353(2) 0.0509(10) Uani 1 1 d U . . H65A H 0.5362 0.6027 0.4019 0.061 Uiso 1 1 calc R . . H65B H 0.4934 0.6724 0.4029 0.061 Uiso 1 1 calc R . . C66 C 0.6311(3) 0.7264(3) 0.4523(2) 0.0603(11) Uani 1 1 d U . . H66A H 0.6304 0.7862 0.4720 0.072 Uiso 1 1 calc R . . H66B H 0.6741 0.7266 0.4931 0.072 Uiso 1 1 calc R . . O25 O 0.6556(2) 0.6948(2) 0.37522(16) 0.0771(9) Uani 1 1 d U . . C69 C 0.8765(3) 0.8695(3) 0.4171(3) 0.0780(13) Uani 1 1 d U . . H69 H 0.9181 0.9236 0.4590 0.094 Uiso 1 1 calc R . . C68 C 0.7945(3) 0.8264(3) 0.4290(3) 0.0673(12) Uani 1 1 d U . . H68 H 0.7789 0.8526 0.4794 0.081 Uiso 1 1 calc R . . C70 C 0.8944(3) 0.8282(4) 0.3393(3) 0.0781(13) Uani 1 1 d U . . C71 C 0.8354(4) 0.7479(4) 0.2763(3) 0.0820(14) Uani 1 1 d U . . H71 H 0.8493 0.7223 0.2250 0.098 Uiso 1 1 calc R . . N12 N 0.9862(4) 0.8713(4) 0.3267(4) 0.1029(16) Uani 1 1 d U . . C72 C 0.7557(3) 0.7066(3) 0.2913(3) 0.0812(14) Uani 1 1 d U . . H72 H 0.7148 0.6519 0.2498 0.097 Uiso 1 1 calc R . . C67 C 0.7351(3) 0.7448(3) 0.3668(3) 0.0650(11) Uani 1 1 d U . . O26 O 0.9990(3) 0.8349(3) 0.2567(3) 0.1446(18) Uani 1 1 d U . . O27 O 1.0412(3) 0.9374(3) 0.3860(3) 0.1346(18) Uani 1 1 d U . . C64 C 0.2938(3) 0.6992(3) 0.7210(3) 0.0786(14) Uani 1 1 d U . . H64 H 0.3028 0.7502 0.7162 0.094 Uiso 1 1 calc R . . N11 N 0.2066(6) 0.6140(7) 0.8598(5) 0.172(3) Uani 1 1 d U . . O24 O 0.1862(6) 0.6734(7) 0.9048(4) 0.253(4) Uani 1 1 d U . . O23 O 0.2032(5) 0.5474(5) 0.8659(4) 0.215(3) Uani 1 1 d U . . H1N H 0.796(3) 0.677(3) 0.799(2) 0.068(15) Uiso 1 1 d . . . H2N H 0.136(2) 1.011(2) 0.119(2) 0.049(11) Uiso 1 1 d . . . H3N H 0.553(3) 0.642(2) 0.535(2) 0.068(11) Uiso 1 1 d . . . O28 O 0.4823(10) 0.3136(11) 0.1503(8) 0.500 Uiso 1 1 d P . . O29 O 0.5705(9) 0.2861(9) 0.0319(8) 0.500 Uiso 1 1 d P . . O30 O 0.4881(10) 0.5717(11) 0.8438(8) 0.500 Uiso 1 1 d P . . 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 Si1 0.0545(7) 0.0394(6) 0.0474(6) 0.0205(5) -0.0058(5) 0.0176(5) F1 0.0920(18) 0.0568(15) 0.0860(17) 0.0461(13) 0.0035(14) 0.0245(13) F4 0.0684(15) 0.0546(14) 0.0766(15) 0.0416(12) -0.0004(12) 0.0170(11) F2 0.115(2) 0.0452(14) 0.0611(14) 0.0120(11) -0.0360(14) 0.0268(13) F6 0.0816(16) 0.0472(13) 0.0590(13) 0.0148(11) -0.0207(12) 0.0268(12) F3 0.0742(16) 0.0897(18) 0.0921(18) 0.0498(15) 0.0189(14) 0.0509(14) F5 0.0943(18) 0.0881(18) 0.0858(17) 0.0538(15) 0.0335(15) 0.0550(15) N1 0.056(2) 0.0424(18) 0.0367(16) 0.0212(14) 0.0078(14) 0.0262(15) C3 0.047(2) 0.0300(18) 0.0328(17) 0.0159(14) 0.0049(15) 0.0131(15) C1 0.067(2) 0.041(2) 0.0335(18) 0.0169(16) 0.0040(17) 0.0278(18) C8 0.053(2) 0.040(2) 0.0332(18) 0.0162(16) 0.0058(16) 0.0082(17) C6 0.062(2) 0.036(2) 0.0364(19) 0.0157(16) -0.0073(18) 0.0106(18) C2 0.062(2) 0.047(2) 0.041(2) 0.0240(17) 0.0115(18) 0.0278(19) C4 0.055(2) 0.040(2) 0.0371(18) 0.0206(16) 0.0127(16) 0.0225(17) C7 0.064(2) 0.032(2) 0.0326(18) 0.0175(16) -0.0053(17) -0.0038(17) C5 0.050(2) 0.044(2) 0.047(2) 0.0193(18) 0.0047(17) 0.0193(18) O1 0.0577(15) 0.0454(15) 0.0419(13) 0.0255(12) 0.0141(12) 0.0273(12) O3 0.118(3) 0.077(2) 0.088(2) 0.062(2) -0.012(2) 0.0158(19) O2 0.135(3) 0.145(4) 0.112(3) 0.082(3) 0.023(3) 0.091(3) N2 0.087(3) 0.053(2) 0.057(2) 0.0267(19) -0.016(2) 0.017(2) C9 0.058(2) 0.046(2) 0.044(2) 0.0213(17) 0.0165(18) 0.0237(18) C16 0.057(3) 0.058(3) 0.062(2) 0.023(2) 0.019(2) 0.021(2) C15 0.043(2) 0.069(3) 0.053(2) 0.007(2) 0.0075(18) 0.018(2) C10 0.082(3) 0.058(3) 0.068(3) 0.042(2) 0.039(2) 0.038(2) C11 0.057(3) 0.068(3) 0.053(2) 0.033(2) 0.0198(19) 0.029(2) C14 0.049(3) 0.103(4) 0.046(2) 0.032(2) 0.0137(19) 0.027(3) C13 0.076(3) 0.104(4) 0.077(3) 0.063(3) 0.036(3) 0.046(3) C12 0.084(3) 0.086(3) 0.075(3) 0.058(3) 0.043(3) 0.052(3) O4 0.087(2) 0.0640(18) 0.0665(17) 0.0438(15) 0.0446(16) 0.0483(16) O6 0.081(2) 0.147(4) 0.062(2) 0.009(2) 0.0236(19) 0.032(2) O5 0.133(4) 0.199(5) 0.117(3) 0.101(4) 0.075(3) 0.067(4) N3 0.054(3) 0.139(5) 0.060(3) 0.038(3) 0.021(2) 0.027(3) C17 0.057(2) 0.054(2) 0.046(2) 0.0294(18) 0.0167(18) 0.0276(19) C18 0.067(3) 0.054(2) 0.056(2) 0.028(2) 0.030(2) 0.031(2) C19 0.079(3) 0.097(3) 0.053(2) 0.039(2) 0.036(2) 0.053(3) O7 0.085(2) 0.0667(19) 0.0711(19) 0.0315(16) 0.0465(17) 0.0332(16) C21 0.063(3) 0.159(5) 0.078(3) -0.026(3) 0.014(3) 0.022(3) C20 0.055(3) 0.115(4) 0.062(3) 0.009(3) 0.022(2) 0.027(3) C22 0.086(4) 0.206(6) 0.048(3) 0.014(4) 0.018(3) 0.070(4) C24 0.113(4) 0.118(4) 0.095(4) 0.060(3) 0.058(3) 0.060(3) C23 0.136(6) 0.199(6) 0.088(4) 0.079(4) 0.075(4) 0.106(5) O8 0.118(5) 0.276(7) 0.140(5) -0.096(4) 0.030(4) 0.022(5) O9 0.257(8) 0.427(10) 0.093(4) 0.074(5) 0.104(4) 0.201(7) N4 0.096(5) 0.300(8) 0.082(4) -0.019(5) 0.034(4) 0.070(6) Si2 0.0445(8) 0.0389(8) 0.0412(8) 0.0211(7) -0.0002(6) 0.0148(6) F9 0.0645(15) 0.0707(16) 0.0877(17) 0.0595(14) -0.0011(12) 0.0145(12) F8 0.119(2) 0.0466(15) 0.0863(17) 0.0262(13) -0.0495(15) 0.0121(14) F7 0.111(2) 0.130(2) 0.119(2) 0.084(2) 0.0647(19) 0.0885(19) N5 0.0511(18) 0.0408(17) 0.0341(15) 0.0237(14) 0.0093(13) 0.0226(14) C25 0.052(2) 0.040(2) 0.0418(19) 0.0213(16) 0.0156(17) 0.0172(17) C26 0.063(3) 0.052(2) 0.066(2) 0.036(2) 0.035(2) 0.030(2) C27 0.053(2) 0.062(3) 0.047(2) 0.030(2) 0.0202(18) 0.021(2) C32 0.062(3) 0.056(3) 0.060(2) 0.025(2) 0.023(2) 0.015(2) C31 0.069(3) 0.071(3) 0.052(2) 0.013(2) 0.023(2) 0.012(2) C28 0.088(3) 0.084(3) 0.068(3) 0.053(3) 0.041(2) 0.046(3) C30 0.076(3) 0.097(4) 0.046(2) 0.031(2) 0.024(2) 0.022(3) C29 0.090(4) 0.105(4) 0.084(3) 0.068(3) 0.045(3) 0.037(3) C35 0.046(2) 0.0322(19) 0.0351(18) 0.0141(15) -0.0013(16) 0.0115(16) C34 0.053(2) 0.043(2) 0.047(2) 0.0270(17) 0.0172(17) 0.0233(17) C33 0.052(2) 0.039(2) 0.0357(18) 0.0173(16) 0.0052(16) 0.0201(17) C39 0.064(3) 0.035(2) 0.040(2) 0.0194(17) -0.0015(18) 0.0049(18) C40 0.051(2) 0.034(2) 0.0379(19) 0.0148(16) 0.0041(16) 0.0080(16) C38 0.063(3) 0.037(2) 0.054(2) 0.0229(18) -0.013(2) 0.0089(18) C36 0.058(2) 0.047(2) 0.057(2) 0.0325(19) 0.0146(19) 0.0202(19) C37 0.057(2) 0.053(3) 0.060(2) 0.026(2) 0.004(2) 0.023(2) O10 0.0749(18) 0.0567(17) 0.0548(15) 0.0365(13) 0.0336(14) 0.0313(14) O11 0.196(5) 0.211(5) 0.132(4) 0.120(4) 0.108(4) 0.079(4) O12 0.180(5) 0.152(4) 0.079(3) 0.027(3) 0.072(3) 0.044(4) N6 0.114(4) 0.144(5) 0.071(3) 0.054(3) 0.049(3) 0.028(4) O13 0.0571(16) 0.0512(15) 0.0547(15) 0.0353(13) 0.0196(12) 0.0276(12) O15 0.103(3) 0.082(2) 0.094(2) 0.066(2) -0.019(2) 0.0123(19) O14 0.175(5) 0.216(5) 0.179(4) 0.144(4) 0.070(4) 0.151(4) N7 0.080(3) 0.075(3) 0.078(3) 0.043(2) -0.013(2) 0.026(2) C41 0.053(2) 0.052(2) 0.043(2) 0.0293(18) 0.0201(17) 0.0230(18) C42 0.072(3) 0.057(3) 0.058(2) 0.030(2) 0.033(2) 0.027(2) C45 0.070(3) 0.055(3) 0.059(2) 0.025(2) 0.012(2) 0.024(2) C44 0.060(3) 0.061(3) 0.058(2) 0.034(2) 0.026(2) 0.024(2) C43 0.057(2) 0.060(3) 0.049(2) 0.025(2) 0.0225(19) 0.031(2) C46 0.081(3) 0.067(3) 0.051(2) 0.028(2) 0.031(2) 0.039(2) C48 0.059(3) 0.058(3) 0.066(3) 0.027(2) 0.028(2) 0.021(2) C47 0.076(3) 0.078(3) 0.069(3) 0.040(2) 0.042(2) 0.042(2) O16 0.0610(17) 0.0659(18) 0.0561(16) 0.0215(14) 0.0294(14) 0.0203(14) O17 0.194(4) 0.067(2) 0.100(3) 0.014(2) 0.060(3) 0.049(3) O18 0.176(4) 0.123(3) 0.086(3) 0.037(2) 0.084(3) 0.062(3) N8 0.118(4) 0.080(3) 0.063(3) 0.031(2) 0.041(2) 0.057(3) N9 0.0430(17) 0.0437(18) 0.0439(16) 0.0273(14) 0.0124(14) 0.0184(14) C51 0.045(2) 0.0318(19) 0.0344(17) 0.0172(15) 0.0064(15) 0.0123(15) C54 0.048(2) 0.0313(19) 0.0338(18) 0.0143(15) -0.0020(16) 0.0110(16) C56 0.044(2) 0.044(2) 0.0353(18) 0.0205(16) 0.0122(15) 0.0172(16) C52 0.052(2) 0.042(2) 0.0383(19) 0.0238(16) 0.0148(16) 0.0192(17) C49 0.053(2) 0.042(2) 0.0380(18) 0.0221(16) 0.0101(16) 0.0158(17) C50 0.053(2) 0.044(2) 0.0403(19) 0.0264(17) 0.0143(16) 0.0218(17) C55 0.052(2) 0.038(2) 0.0334(18) 0.0190(16) 0.0029(16) 0.0059(17) C53 0.044(2) 0.042(2) 0.045(2) 0.0176(17) 0.0102(17) 0.0180(17) O19 0.0521(15) 0.0526(15) 0.0465(14) 0.0347(12) 0.0187(12) 0.0282(12) O20 0.093(2) 0.090(2) 0.084(2) 0.068(2) 0.0117(18) 0.0308(18) O21 0.116(3) 0.112(3) 0.108(3) 0.072(2) 0.038(2) 0.081(2) N10 0.068(2) 0.048(2) 0.051(2) 0.0255(17) -0.0052(17) 0.0166(17) C57 0.045(2) 0.043(2) 0.049(2) 0.0205(17) 0.0062(17) 0.0149(17) C58 0.054(2) 0.051(2) 0.067(3) 0.034(2) 0.015(2) 0.0179(19) O22 0.0589(17) 0.0537(16) 0.0528(15) 0.0274(13) 0.0195(13) 0.0197(13) C59 0.041(2) 0.080(3) 0.060(3) 0.039(2) 0.0077(19) 0.006(2) C63 0.070(3) 0.126(5) 0.052(3) 0.014(3) 0.011(2) -0.002(3) C62 0.081(4) 0.157(6) 0.078(4) 0.062(4) 0.016(3) -0.004(4) C60 0.085(4) 0.099(4) 0.100(4) 0.067(3) 0.024(3) 0.014(3) C61 0.094(4) 0.143(5) 0.115(5) 0.097(4) 0.027(4) 0.008(4) C65 0.056(2) 0.058(2) 0.047(2) 0.0270(19) 0.0163(18) 0.0269(19) C66 0.054(2) 0.083(3) 0.054(2) 0.040(2) 0.023(2) 0.026(2) O25 0.0650(19) 0.094(2) 0.0618(18) 0.0339(17) 0.0277(15) 0.0168(16) C69 0.083(3) 0.082(3) 0.096(3) 0.056(3) 0.045(3) 0.039(3) C68 0.063(3) 0.083(3) 0.073(3) 0.045(2) 0.032(2) 0.033(2) C70 0.079(3) 0.094(3) 0.118(4) 0.079(3) 0.058(3) 0.051(3) C71 0.099(4) 0.091(4) 0.091(3) 0.059(3) 0.053(3) 0.050(3) N12 0.112(4) 0.100(4) 0.160(5) 0.097(4) 0.082(4) 0.055(3) C72 0.083(3) 0.093(4) 0.075(3) 0.041(3) 0.041(3) 0.034(3) C67 0.064(3) 0.083(3) 0.068(3) 0.046(2) 0.033(2) 0.033(2) O26 0.174(4) 0.136(4) 0.184(4) 0.101(3) 0.140(4) 0.075(3) O27 0.108(3) 0.114(4) 0.191(5) 0.090(3) 0.063(3) 0.019(3) C64 0.061(3) 0.089(3) 0.054(3) 0.019(2) 0.013(2) 0.011(3) N11 0.151(6) 0.210(8) 0.101(5) 0.078(5) 0.034(4) -0.018(6) O24 0.265(8) 0.313(9) 0.140(6) 0.093(6) 0.125(6) 0.052(7) O23 0.193(6) 0.275(8) 0.146(5) 0.138(5) 0.046(4) -0.021(5) _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 Si1 F3 1.653(3) . ? Si1 F5 1.667(3) . ? Si1 F1 1.667(2) . ? Si1 F4 1.673(2) . ? Si1 F2 1.696(2) . ? Si1 F6 1.698(2) . ? N1 C9 1.489(5) . ? N1 C17 1.501(4) . ? N1 C1 1.510(4) . ? C3 O1 1.371(4) . ? C3 C4 1.367(5) . ? C3 C8 1.393(4) . ? C1 C2 1.505(5) . ? C8 C7 1.373(5) . ? C6 C5 1.343(5) . ? C6 C7 1.380(5) . ? C6 N2 1.463(5) . ? C2 O1 1.431(4) . ? C4 C5 1.377(5) . ? O3 N2 1.223(5) . ? O2 N2 1.229(5) . ? C9 C10 1.495(5) . ? C16 C11 1.379(5) . ? C16 C15 1.389(5) . ? C15 C14 1.377(6) . ? C10 O4 1.429(4) . ? C11 O4 1.364(4) . ? C11 C12 1.390(6) . ? C14 C13 1.370(6) . ? C14 N3 1.472(6) . ? C13 C12 1.365(5) . ? O6 N3 1.202(6) . ? O5 N3 1.236(6) . ? C17 C18 1.509(5) . ? C18 O7 1.416(4) . ? C19 O7 1.355(5) . ? C19 C20 1.365(6) . ? C19 C24 1.386(6) . ? C21 C22 1.348(9) . ? C21 C20 1.377(6) . ? C22 C23 1.345(9) . ? C22 N4 1.456(8) . ? C24 C23 1.408(7) . ? O8 N4 1.204(13) . ? O9 N4 1.214(11) . ? Si2 F7 1.647(2) . ? Si2 F7 1.647(2) 2_777 ? Si2 F9 1.673(2) . ? Si2 F9 1.673(2) 2_777 ? Si2 F8 1.681(2) 2_777 ? Si2 F8 1.681(2) . ? N5 C25 1.495(4) . ? N5 C41 1.502(4) . ? N5 C33 1.517(4) . ? C25 C26 1.491(5) . ? C26 O10 1.453(4) . ? C27 O10 1.370(4) . ? C27 C32 1.374(5) . ? C27 C28 1.388(5) . ? C32 C31 1.386(5) . ? C31 C30 1.386(6) . ? C28 C29 1.376(5) . ? C30 C29 1.366(7) . ? C30 N6 1.466(6) . ? C35 O13 1.363(4) . ? C35 C36 1.368(5) . ? C35 C40 1.404(5) . ? C34 O13 1.433(4) . ? C34 C33 1.495(4) . ? C39 C40 1.355(5) . ? C39 C38 1.367(5) . ? C38 C37 1.372(5) . ? C38 N7 1.456(5) . ? C36 C37 1.393(5) . ? O11 N6 1.245(7) . ? O12 N6 1.224(7) . ? O15 N7 1.201(5) . ? O14 N7 1.210(5) . ? C41 C42 1.504(5) . ? C42 O16 1.423(4) . ? C45 C46 1.383(6) . ? C45 C44 1.384(5) . ? C44 C43 1.379(5) . ? C43 O16 1.362(4) . ? C43 C48 1.363(5) . ? C46 C47 1.371(6) . ? C46 N8 1.461(5) . ? C48 C47 1.371(5) . ? O17 N8 1.202(5) . ? O18 N8 1.243(5) . ? N9 C65 1.499(4) . ? N9 C57 1.500(4) . ? N9 C49 1.522(4) . ? C51 O19 1.360(4) . ? C51 C52 1.387(5) . ? C51 C56 1.388(4) . ? C54 C55 1.373(5) . ? C54 C53 1.380(5) . ? C54 N10 1.448(5) . ? C56 C55 1.383(5) . ? C52 C53 1.380(5) . ? C49 C50 1.500(5) . ? C50 O19 1.424(4) . ? O20 N10 1.210(4) . ? O21 N10 1.212(4) . ? C57 C58 1.494(5) . ? C58 O22 1.446(4) . ? O22 C59 1.368(5) . ? C59 C64 1.370(6) . ? C59 C60 1.380(6) . ? C63 C62 1.341(9) . ? C63 C64 1.387(6) . ? C62 C61 1.348(9) . ? C62 N11 1.500(9) . ? C60 C61 1.393(7) . ? C65 C66 1.488(5) . ? C66 O25 1.416(4) . ? O25 C67 1.368(5) . ? C69 C68 1.377(6) . ? C69 C70 1.394(6) . ? C68 C67 1.381(6) . ? C70 C71 1.372(6) . ? C70 N12 1.503(6) . ? C71 C72 1.367(6) . ? N12 O27 1.214(6) . ? N12 O26 1.232(6) . ? C72 C67 1.370(5) . ? N11 O24 1.170(11) . ? N11 O23 1.236(11) . ? 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 F3 Si1 F5 179.66(13) . . ? F3 Si1 F1 88.80(14) . . ? F5 Si1 F1 91.39(14) . . ? F3 Si1 F4 91.05(13) . . ? F5 Si1 F4 88.76(13) . . ? F1 Si1 F4 179.85(15) . . ? F3 Si1 F2 89.46(14) . . ? F5 Si1 F2 90.82(14) . . ? F1 Si1 F2 89.09(12) . . ? F4 Si1 F2 90.96(12) . . ? F3 Si1 F6 90.46(13) . . ? F5 Si1 F6 89.26(13) . . ? F1 Si1 F6 91.18(12) . . ? F4 Si1 F6 88.77(12) . . ? F2 Si1 F6 179.72(15) . . ? C9 N1 C17 112.5(3) . . ? C9 N1 C1 115.5(3) . . ? C17 N1 C1 111.2(3) . . ? O1 C3 C4 124.4(3) . . ? O1 C3 C8 115.1(3) . . ? C4 C3 C8 120.5(3) . . ? C2 C1 N1 115.8(3) . . ? C7 C8 C3 119.4(4) . . ? C5 C6 C7 120.9(4) . . ? C5 C6 N2 120.4(4) . . ? C7 C6 N2 118.6(4) . . ? O1 C2 C1 109.9(3) . . ? C3 C4 C5 119.0(3) . . ? C8 C7 C6 119.2(3) . . ? C6 C5 C4 120.9(4) . . ? C3 O1 C2 117.0(3) . . ? O3 N2 O2 123.9(4) . . ? O3 N2 C6 118.3(4) . . ? O2 N2 C6 117.8(4) . . ? C10 C9 N1 115.0(3) . . ? C11 C16 C15 119.7(4) . . ? C14 C15 C16 118.3(4) . . ? O4 C10 C9 108.8(3) . . ? O4 C11 C16 115.0(4) . . ? O4 C11 C12 124.6(4) . . ? C16 C11 C12 120.4(4) . . ? C13 C14 C15 122.4(4) . . ? C13 C14 N3 119.6(5) . . ? C15 C14 N3 118.0(5) . . ? C12 C13 C14 119.1(5) . . ? C13 C12 C11 120.0(4) . . ? C11 O4 C10 119.4(3) . . ? O6 N3 O5 123.8(5) . . ? O6 N3 C14 118.6(6) . . ? O5 N3 C14 117.5(5) . . ? N1 C17 C18 114.2(3) . . ? O7 C18 C17 103.5(3) . . ? O7 C19 C20 124.8(4) . . ? O7 C19 C24 113.9(5) . . ? C20 C19 C24 121.3(4) . . ? C19 O7 C18 118.8(3) . . ? C22 C21 C20 120.6(6) . . ? C19 C20 C21 118.7(5) . . ? C21 C22 C23 122.0(6) . . ? C21 C22 N4 121.3(8) . . ? C23 C22 N4 116.6(8) . . ? C19 C24 C23 118.2(6) . . ? C22 C23 C24 119.2(6) . . ? O9 N4 O8 123.0(8) . . ? O9 N4 C22 119.8(10) . . ? O8 N4 C22 117.1(9) . . ? F7 Si2 F7 180.0(2) . 2_777 ? F7 Si2 F9 87.87(13) . . ? F7 Si2 F9 92.13(13) 2_777 . ? F7 Si2 F9 92.13(13) . 2_777 ? F7 Si2 F9 87.87(13) 2_777 2_777 ? F9 Si2 F9 180.00(8) . 2_777 ? F7 Si2 F8 88.32(16) . 2_777 ? F7 Si2 F8 91.68(16) 2_777 2_777 ? F9 Si2 F8 90.15(11) . 2_777 ? F9 Si2 F8 89.85(12) 2_777 2_777 ? F7 Si2 F8 91.68(16) . . ? F7 Si2 F8 88.32(16) 2_777 . ? F9 Si2 F8 89.85(12) . . ? F9 Si2 F8 90.15(11) 2_777 . ? F8 Si2 F8 180.000(1) 2_777 . ? C25 N5 C41 112.3(3) . . ? C25 N5 C33 115.3(3) . . ? C41 N5 C33 112.1(3) . . ? C26 C25 N5 114.1(3) . . ? O10 C26 C25 108.1(3) . . ? O10 C27 C32 114.8(4) . . ? O10 C27 C28 124.2(4) . . ? C32 C27 C28 121.0(4) . . ? C27 C32 C31 119.9(4) . . ? C30 C31 C32 118.3(4) . . ? C27 C28 C29 119.1(4) . . ? C29 C30 C31 121.8(4) . . ? C29 C30 N6 120.0(5) . . ? C31 C30 N6 118.1(5) . . ? C30 C29 C28 119.8(5) . . ? O13 C35 C36 124.6(3) . . ? O13 C35 C40 115.2(3) . . ? C36 C35 C40 120.2(4) . . ? O13 C34 C33 109.4(3) . . ? C34 C33 N5 116.3(3) . . ? C40 C39 C38 119.2(4) . . ? C39 C40 C35 120.3(4) . . ? C39 C38 C37 121.7(4) . . ? C39 C38 N7 118.6(4) . . ? C37 C38 N7 119.7(4) . . ? C35 C36 C37 119.0(4) . . ? C38 C37 C36 119.4(4) . . ? C27 O10 C26 118.9(3) . . ? O12 N6 O11 124.3(5) . . ? O12 N6 C30 118.9(6) . . ? O11 N6 C30 116.8(6) . . ? C35 O13 C34 117.7(3) . . ? O15 N7 O14 122.1(5) . . ? O15 N7 C38 120.4(5) . . ? O14 N7 C38 117.4(5) . . ? C42 C41 N5 112.3(3) . . ? O16 C42 C41 105.4(3) . . ? C46 C45 C44 119.0(4) . . ? C45 C44 C43 118.9(4) . . ? O16 C43 C48 114.9(4) . . ? O16 C43 C44 124.3(4) . . ? C48 C43 C44 120.8(4) . . ? C47 C46 C45 122.0(4) . . ? C47 C46 N8 119.4(4) . . ? C45 C46 N8 118.6(4) . . ? C43 C48 C47 121.3(4) . . ? C46 C47 C48 117.9(4) . . ? C43 O16 C42 118.6(3) . . ? O17 N8 O18 124.0(4) . . ? O17 N8 C46 119.3(5) . . ? O18 N8 C46 116.7(5) . . ? C65 N9 C57 107.9(3) . . ? C65 N9 C49 115.2(3) . . ? C57 N9 C49 114.7(3) . . ? O19 C51 C52 124.3(3) . . ? O19 C51 C56 115.5(3) . . ? C52 C51 C56 120.2(3) . . ? C55 C54 C53 121.6(3) . . ? C55 C54 N10 118.5(3) . . ? C53 C54 N10 119.9(4) . . ? C55 C56 C51 120.5(3) . . ? C53 C52 C51 119.3(3) . . ? C50 C49 N9 116.0(3) . . ? O19 C50 C49 108.4(3) . . ? C54 C55 C56 118.7(3) . . ? C52 C53 C54 119.8(3) . . ? C51 O19 C50 118.6(3) . . ? O20 N10 O21 121.9(4) . . ? O20 N10 C54 118.8(4) . . ? O21 N10 C54 119.3(4) . . ? C58 C57 N9 115.0(3) . . ? O22 C58 C57 108.9(3) . . ? C59 O22 C58 116.7(3) . . ? C64 C59 O22 115.2(4) . . ? C64 C59 C60 120.2(5) . . ? O22 C59 C60 124.5(5) . . ? C62 C63 C64 118.1(6) . . ? C63 C62 C61 123.5(7) . . ? C63 C62 N11 116.7(8) . . ? C61 C62 N11 119.8(8) . . ? C61 C60 C59 118.7(6) . . ? C62 C61 C60 119.0(7) . . ? C66 C65 N9 115.6(3) . . ? O25 C66 C65 104.2(3) . . ? C67 O25 C66 119.4(3) . . ? C68 C69 C70 116.9(5) . . ? C67 C68 C69 120.7(4) . . ? C71 C70 C69 123.2(4) . . ? C71 C70 N12 119.0(5) . . ? C69 C70 N12 117.6(5) . . ? C72 C71 C70 117.9(5) . . ? O27 N12 O26 126.0(5) . . ? O27 N12 C70 117.7(5) . . ? O26 N12 C70 116.2(6) . . ? C67 C72 C71 120.9(5) . . ? C72 C67 O25 115.2(4) . . ? C72 C67 C68 120.4(4) . . ? O25 C67 C68 124.4(4) . . ? C59 C64 C63 120.4(6) . . ? O24 N11 O23 126.2(10) . . ? O24 N11 C62 119.0(10) . . ? O23 N11 C62 114.7(9) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 30.07 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.906 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.095