# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data__kusu105 _database_code_depnum_ccdc_archive 'CCDC 920475' #TrackingRef '16977_web_deposit_cif_file_0_TakahiroKusukawa_1358505389.1a.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H20 Cl2 N4 O ' _chemical_formula_moiety 'C16 H20 Cl2 N4 O ' _chemical_formula_weight 355.27 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,+Z #------------------------------------------------------------------------------ _cell_length_a 10.8452(19) _cell_length_b 20.440(3) _cell_length_c 8.5123(18) _cell_angle_alpha 90.0000 _cell_angle_beta 106.969(15) _cell_angle_gamma 90.0000 _cell_volume 1804.8(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25.2 _cell_measurement_theta_max 27.8 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744.00 _exptl_absorpt_coefficient_mu 3.309 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.492 _exptl_absorpt_correction_T_max 0.516 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 4345 _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_theta_max 66.72 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 66.72 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 2.47 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3177 _reflns_number_gt 1922 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1532 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3177 _refine_ls_number_parameters 229 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0683P)^2^+0.1823P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 0.45 _refine_diff_density_min -0.31 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.364 0.702 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl(1) Cl -0.34789(8) 0.28527(4) 0.51857(11) 0.0470(2) Uani 1.00 1 d . . . Cl(2) Cl -0.15323(9) 0.42737(5) 0.10996(11) 0.0557(2) Uani 1.00 1 d . . . O(1) O -0.2195(4) 0.41684(16) 0.4502(5) 0.0991(12) Uani 1.00 1 d . . . N(1) N -0.0542(3) 0.2501(2) 0.6967(4) 0.0685(11) Uani 1.00 1 d . . . N(2) N -0.1240(3) 0.32622(17) 0.8431(4) 0.0531(8) Uani 1.00 1 d . . . N(3) N 0.0898(3) 0.36267(15) 0.3813(4) 0.0557(8) Uani 1.00 1 d . . . N(4) N 0.1095(3) 0.47245(15) 0.3698(4) 0.0617(9) Uani 1.00 1 d . . . C(1) C 0.1005(3) 0.29551(17) 0.9371(4) 0.0420(7) Uani 1.00 1 d . . . C(2) C 0.1366(3) 0.2473(2) 1.0564(4) 0.0559(9) Uani 1.00 1 d . . . C(3) C 0.2566(4) 0.2510(2) 1.1727(4) 0.0590(10) Uani 1.00 1 d . . . C(4) C 0.3376(3) 0.3027(2) 1.1700(4) 0.0505(9) Uani 1.00 1 d . . . C(5) C 0.5057(3) 0.42334(18) 0.8199(5) 0.0569(10) Uani 1.00 1 d . . . C(6) C 0.5041(3) 0.42901(19) 0.6580(5) 0.0603(11) Uani 1.00 1 d . . . C(7) C 0.3878(3) 0.42642(18) 0.5339(5) 0.0553(10) Uani 1.00 1 d . . . C(8) C 0.2731(3) 0.41527(16) 0.5748(4) 0.0444(8) Uani 1.00 1 d . . . C(9) C 0.1554(3) 0.39704(17) 0.7940(4) 0.0430(8) Uani 1.00 1 d . . . C(10) C 0.3891(3) 0.40605(19) 1.0365(4) 0.0520(9) Uani 1.00 1 d . . . C(11) C 0.2743(3) 0.40817(15) 0.7376(4) 0.0415(8) Uani 1.00 1 d . . . C(12) C 0.3926(3) 0.41313(16) 0.8608(4) 0.0471(9) Uani 1.00 1 d . . . C(13) C 0.1833(3) 0.34609(16) 0.9282(3) 0.0375(7) Uani 1.00 1 d . . . C(14) C 0.3035(3) 0.34987(16) 1.0495(4) 0.0413(7) Uani 1.00 1 d . . . C(15) C -0.0315(3) 0.29071(17) 0.8204(4) 0.0415(7) Uani 1.00 1 d . . . C(16) C 0.1517(3) 0.41624(17) 0.4372(4) 0.0455(8) Uani 1.00 1 d . . . H(1) H 0.0805 0.2124 1.0585 0.067 Uiso 1.00 1 c R . . H(2) H 0.2827 0.2184 1.2533 0.071 Uiso 1.00 1 c R . . H(3) H 0.4173 0.3058 1.2516 0.061 Uiso 1.00 1 c R . . H(4) H 0.5844 0.4264 0.9034 0.068 Uiso 1.00 1 c R . . H(5) H 0.5817 0.4346 0.6315 0.072 Uiso 1.00 1 c R . . H(6) H 0.3860 0.4321 0.4236 0.066 Uiso 1.00 1 c R . . H(7) H 0.1301 0.4382 0.8351 0.052 Uiso 1.00 1 c R . . H(8) H 0.0838 0.3824 0.7010 0.052 Uiso 1.00 1 c R . . H(9) H 0.4764 0.3984 1.1088 0.062 Uiso 1.00 1 c R . . H(10) H 0.3564 0.4465 1.0717 0.062 Uiso 1.00 1 c R . . H(11) H -0.142(4) 0.2435(19) 0.624(4) 0.057(11) Uiso 1.00 1 c . . . H(12) H 0.011(4) 0.223(2) 0.683(5) 0.091(16) Uiso 1.00 1 c . . . H(13) H -0.214(2) 0.327(2) 0.769(5) 0.112(19) Uiso 1.00 1 c . . . H(14) H -0.110(3) 0.3510(18) 0.929(4) 0.052(11) Uiso 1.00 1 c . . . H(18) H 0.1460 0.5029 0.4153 0.057 Uiso 1.00 1 c R . . H(16) H 0.1136 0.3270 0.4228 0.051 Uiso 1.00 1 c R . . H(17) H 0.0272 0.4790 0.2663 0.147 Uiso 1.00 1 c R . . H(15) H 0.014(2) 0.3688(18) 0.288(3) 0.061(11) Uiso 1.00 1 c . . . H(19) H -0.1680 0.4066 0.4667 0.000 Uiso 1.00 1 c R . . H(20) H -0.2881 0.4267 0.4119 0.000 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(1) 0.0365(4) 0.0468(4) 0.0546(5) -0.0105(3) 0.0086(3) -0.0069(4) Cl(2) 0.0526(5) 0.0509(5) 0.0507(5) 0.0062(4) -0.0054(4) -0.0124(4) O(1) 0.115(3) 0.070(2) 0.109(2) -0.017(2) 0.028(2) -0.010(2) N(1) 0.0340(17) 0.085(2) 0.079(2) 0.0057(17) 0.0046(16) -0.040(2) N(2) 0.0352(16) 0.067(2) 0.0549(19) 0.0018(15) 0.0101(14) -0.0209(17) N(3) 0.0528(19) 0.0346(15) 0.063(2) 0.0048(13) -0.0095(16) 0.0027(14) N(4) 0.075(2) 0.0334(15) 0.0607(19) -0.0001(15) -0.0052(17) 0.0047(14) C(1) 0.0335(16) 0.046(2) 0.0460(18) 0.0050(15) 0.0111(14) 0.0014(15) C(2) 0.053(2) 0.058(2) 0.062(2) -0.0015(18) 0.0245(19) 0.0113(19) C(3) 0.054(2) 0.068(2) 0.054(2) 0.011(2) 0.0149(18) 0.018(2) C(4) 0.0391(18) 0.066(2) 0.0397(18) 0.0142(17) 0.0014(15) -0.0010(17) C(5) 0.0389(19) 0.044(2) 0.075(2) -0.0085(16) -0.0021(19) 0.0059(19) C(6) 0.040(2) 0.049(2) 0.091(3) -0.0090(17) 0.019(2) 0.002(2) C(7) 0.054(2) 0.047(2) 0.064(2) -0.0063(18) 0.0156(19) 0.0042(18) C(8) 0.0381(18) 0.0362(18) 0.053(2) -0.0034(14) 0.0043(16) 0.0073(15) C(9) 0.0282(16) 0.0388(18) 0.052(2) -0.0022(13) -0.0043(14) 0.0026(15) C(10) 0.0379(19) 0.051(2) 0.053(2) -0.0026(16) -0.0092(16) -0.0041(17) C(11) 0.0321(17) 0.0265(15) 0.055(2) -0.0018(12) -0.0038(14) 0.0022(14) C(12) 0.0329(17) 0.0341(17) 0.063(2) -0.0079(13) -0.0041(16) 0.0018(16) C(13) 0.0308(16) 0.0385(17) 0.0385(17) 0.0072(13) 0.0028(13) -0.0026(13) C(14) 0.0360(17) 0.0400(17) 0.0437(17) 0.0020(14) 0.0049(14) -0.0040(15) C(15) 0.0337(16) 0.0415(18) 0.0513(19) -0.0026(15) 0.0155(14) -0.0020(16) C(16) 0.0446(19) 0.0393(18) 0.0473(19) -0.0006(15) 0.0053(16) 0.0010(15) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N(1) C(15) 1.307(5) yes . . N(2) C(15) 1.298(5) yes . . N(3) C(16) 1.300(4) yes . . N(4) C(16) 1.306(4) yes . . C(1) C(2) 1.388(5) yes . . C(1) C(13) 1.386(4) yes . . C(1) C(15) 1.488(4) yes . . C(2) C(3) 1.389(5) yes . . C(3) C(4) 1.378(6) yes . . C(4) C(14) 1.377(4) yes . . C(5) C(6) 1.377(6) yes . . C(5) C(12) 1.385(6) yes . . C(6) C(7) 1.390(5) yes . . C(7) C(8) 1.405(6) yes . . C(8) C(11) 1.390(5) yes . . C(8) C(16) 1.486(4) yes . . C(9) C(11) 1.519(5) yes . . C(9) C(13) 1.510(4) yes . . C(10) C(12) 1.514(5) yes . . C(10) C(14) 1.501(5) yes . . C(11) C(12) 1.404(4) yes . . C(13) C(14) 1.409(4) yes . . N(1) H(11) 0.99(3) no . . N(1) H(12) 0.93(5) no . . N(2) H(13) 0.99(2) no . . N(2) H(14) 0.87(3) no . . N(3) H(16) 0.818 no . . N(3) H(15) 0.97(2) no . . N(4) H(18) 0.777 no . . N(4) H(17) 1.064 no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.980 no . . C(9) H(8) 0.980 no . . C(10) H(9) 0.980 no . . C(10) H(10) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(13) 121.4(2) yes . . . C(2) C(1) C(15) 116.9(3) yes . . . C(13) C(1) C(15) 121.7(2) yes . . . C(1) C(2) C(3) 119.2(3) yes . . . C(2) C(3) C(4) 120.0(3) yes . . . C(3) C(4) C(14) 121.0(3) yes . . . C(6) C(5) C(12) 120.7(3) yes . . . C(5) C(6) C(7) 120.1(4) yes . . . C(6) C(7) C(8) 119.4(4) yes . . . C(7) C(8) C(11) 120.9(3) yes . . . C(7) C(8) C(16) 116.6(3) yes . . . C(11) C(8) C(16) 122.4(3) yes . . . C(11) C(9) C(13) 110.0(2) yes . . . C(12) C(10) C(14) 109.9(2) yes . . . C(8) C(11) C(9) 124.7(2) yes . . . C(8) C(11) C(12) 118.5(3) yes . . . C(9) C(11) C(12) 116.7(3) yes . . . C(5) C(12) C(10) 122.9(3) yes . . . C(5) C(12) C(11) 120.4(3) yes . . . C(10) C(12) C(11) 116.7(3) yes . . . C(1) C(13) C(9) 124.5(2) yes . . . C(1) C(13) C(14) 118.5(2) yes . . . C(9) C(13) C(14) 117.1(2) yes . . . C(4) C(14) C(10) 123.6(2) yes . . . C(4) C(14) C(13) 119.8(3) yes . . . C(10) C(14) C(13) 116.6(2) yes . . . N(1) C(15) N(2) 120.2(3) yes . . . N(1) C(15) C(1) 119.8(3) yes . . . N(2) C(15) C(1) 119.9(3) yes . . . N(3) C(16) N(4) 120.2(3) yes . . . N(3) C(16) C(8) 121.4(3) yes . . . N(4) C(16) C(8) 118.3(3) yes . . . H(19) O(1) H(20) 168.0 no . . . C(15) N(1) H(11) 121(2) no . . . C(15) N(1) H(12) 121(2) no . . . H(11) N(1) H(12) 118(3) no . . . C(15) N(2) H(13) 125(2) no . . . C(15) N(2) H(14) 120(2) no . . . H(13) N(2) H(14) 115(3) no . . . C(16) N(3) H(16) 121.9 no . . . C(16) N(3) H(15) 115(2) no . . . H(16) N(3) H(15) 123.6 no . . . C(16) N(4) H(18) 115.1 no . . . C(16) N(4) H(17) 125.2 no . . . H(18) N(4) H(17) 119.5 no . . . C(1) C(2) H(1) 120.4 no . . . C(3) C(2) H(1) 120.4 no . . . C(2) C(3) H(2) 120.0 no . . . C(4) C(3) H(2) 120.0 no . . . C(3) C(4) H(3) 119.5 no . . . C(14) C(4) H(3) 119.5 no . . . C(6) C(5) H(4) 119.7 no . . . C(12) C(5) H(4) 119.6 no . . . C(5) C(6) H(5) 120.0 no . . . C(7) C(6) H(5) 120.0 no . . . C(6) C(7) H(6) 120.3 no . . . C(8) C(7) H(6) 120.3 no . . . C(11) C(9) H(7) 109.7 no . . . C(11) C(9) H(8) 109.7 no . . . C(13) C(9) H(7) 109.7 no . . . C(13) C(9) H(8) 109.7 no . . . H(7) C(9) H(8) 108.2 no . . . C(12) C(10) H(9) 109.7 no . . . C(12) C(10) H(10) 109.7 no . . . C(14) C(10) H(9) 109.7 no . . . C(14) C(10) H(10) 109.7 no . . . H(9) C(10) H(10) 108.2 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(13) C(9) 174.7(3) ? . . . . C(2) C(1) C(13) C(14) -3.6(5) ? . . . . C(13) C(1) C(2) C(3) 2.2(6) ? . . . . C(2) C(1) C(15) N(1) -79.5(5) ? . . . . C(2) C(1) C(15) N(2) 99.6(4) ? . . . . C(15) C(1) C(2) C(3) -177.2(3) ? . . . . C(13) C(1) C(15) N(1) 101.0(4) ? . . . . C(13) C(1) C(15) N(2) -79.9(5) ? . . . . C(15) C(1) C(13) C(9) -5.9(5) ? . . . . C(15) C(1) C(13) C(14) 175.8(3) ? . . . . C(1) C(2) C(3) C(4) 0.8(6) ? . . . . C(2) C(3) C(4) C(14) -2.4(6) ? . . . . C(3) C(4) C(14) C(10) -177.9(4) ? . . . . C(3) C(4) C(14) C(13) 1.0(6) ? . . . . C(6) C(5) C(12) C(10) 179.5(3) ? . . . . C(6) C(5) C(12) C(11) 0.2(4) ? . . . . C(12) C(5) C(6) C(7) 1.9(5) ? . . . . C(5) C(6) C(7) C(8) -2.6(5) ? . . . . C(6) C(7) C(8) C(11) 1.3(5) ? . . . . C(6) C(7) C(8) C(16) 177.2(3) ? . . . . C(7) C(8) C(11) C(9) 179.0(3) ? . . . . C(7) C(8) C(11) C(12) 0.7(4) ? . . . . C(7) C(8) C(16) N(3) 106.2(4) ? . . . . C(7) C(8) C(16) N(4) -72.1(5) ? . . . . C(11) C(8) C(16) N(3) -78.1(5) ? . . . . C(11) C(8) C(16) N(4) 103.7(4) ? . . . . C(16) C(8) C(11) C(9) 3.4(5) ? . . . . C(16) C(8) C(11) C(12) -174.9(3) ? . . . . C(11) C(9) C(13) C(1) -136.2(3) ? . . . . C(11) C(9) C(13) C(14) 42.1(4) ? . . . . C(13) C(9) C(11) C(8) 137.9(3) ? . . . . C(13) C(9) C(11) C(12) -43.7(3) ? . . . . C(12) C(10) C(14) C(4) 133.1(3) ? . . . . C(12) C(10) C(14) C(13) -45.8(4) ? . . . . C(14) C(10) C(12) C(5) -135.3(3) ? . . . . C(14) C(10) C(12) C(11) 44.1(4) ? . . . . C(8) C(11) C(12) C(5) -1.5(4) ? . . . . C(8) C(11) C(12) C(10) 179.1(3) ? . . . . C(9) C(11) C(12) C(5) -179.9(2) ? . . . . C(9) C(11) C(12) C(10) 0.7(4) ? . . . . C(1) C(13) C(14) C(4) 2.0(5) ? . . . . C(1) C(13) C(14) C(10) -179.0(3) ? . . . . C(9) C(13) C(14) C(4) -176.4(3) ? . . . . C(9) C(13) C(14) C(10) 2.6(5) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Cl(1) O(1) 3.160(3) ? . . Cl(1) N(1) 3.185(3) ? . . Cl(1) N(1) 3.131(4) ? . 4_455 Cl(1) N(2) 3.211(3) ? . . Cl(1) N(3) 3.241(3) ? . 4_455 Cl(1) C(3) 3.529(4) ? . 4_454 Cl(2) O(1) 3.188(4) ? . . Cl(2) N(2) 3.155(3) ? . 1_554 Cl(2) N(3) 3.237(3) ? . . Cl(2) N(4) 3.191(3) ? . . O(1) Cl(1) 3.160(3) ? . . O(1) Cl(2) 3.188(4) ? . . O(1) N(4) 2.797(4) ? . 3_566 O(1) C(8) 3.477(4) ? . 3_566 O(1) C(16) 3.562(4) ? . 3_566 N(1) Cl(1) 3.185(3) ? . . N(1) Cl(1) 3.131(4) ? . 4_555 N(2) Cl(1) 3.211(3) ? . . N(2) Cl(2) 3.155(3) ? . 1_556 N(3) Cl(1) 3.241(3) ? . 4_555 N(3) Cl(2) 3.237(3) ? . . N(4) Cl(2) 3.191(3) ? . . N(4) O(1) 2.797(4) ? . 3_566 C(3) Cl(1) 3.529(4) ? . 4_556 C(8) O(1) 3.477(4) ? . 3_566 C(16) O(1) 3.562(4) ? . 3_566 Cl(1) H(2) 2.996 ? . 4_454 Cl(1) H(3) 2.906 ? . 1_454 Cl(1) H(5) 3.355 ? . 1_455 Cl(1) H(11) 2.31(4) ? . . Cl(1) H(12) 2.36(5) ? . 4_455 Cl(1) H(13) 2.36(4) ? . . Cl(1) H(16) 2.430 ? . 4_455 Cl(1) H(19) 3.265 ? . . Cl(1) H(20) 3.153 ? . . Cl(2) H(2) 3.368 ? . 4_454 Cl(2) H(4) 2.876 ? . 1_454 Cl(2) H(7) 2.787 ? . 3_566 Cl(2) H(10) 3.450 ? . 3_566 Cl(2) H(13) 3.45(4) ? . 1_554 Cl(2) H(14) 2.33(4) ? . 1_554 Cl(2) H(17) 2.280 ? . . Cl(2) H(15) 2.32(2) ? . . Cl(2) H(19) 3.116 ? . . Cl(2) H(20) 3.307 ? . . O(1) H(2) 3.235 ? . 4_454 O(1) H(5) 3.018 ? . 1_455 O(1) H(8) 3.431 ? . . O(1) H(13) 3.26(4) ? . . O(1) H(18) 2.026 ? . 3_566 O(1) H(17) 3.430 ? . 3_566 O(1) H(15) 3.36(3) ? . . O(1) H(19) 0.574 ? . . O(1) H(20) 0.747 ? . . N(2) H(19) 3.508 ? . . N(3) H(2) 3.593 ? . 4_454 N(3) H(19) 3.215 ? . . N(4) H(7) 3.238 ? . 3_566 N(4) H(8) 3.581 ? . 3_566 N(4) H(19) 2.816 ? . 3_566 N(4) H(20) 3.059 ? . 3_566 C(2) H(3) 3.450 ? . 4_455 C(2) H(9) 3.540 ? . 4_455 C(2) H(16) 3.592 ? . 1_556 C(3) H(14) 3.54(4) ? . 4_555 C(3) H(16) 3.358 ? . 1_556 C(4) H(1) 3.066 ? . 4_555 C(4) H(6) 3.357 ? . 1_556 C(5) H(1) 3.395 ? . 4_555 C(5) H(10) 3.060 ? . 3_667 C(5) H(12) 3.22(4) ? . 4_555 C(6) H(6) 3.233 ? . 3_666 C(6) H(10) 3.468 ? . 3_667 C(6) H(12) 3.12(4) ? . 4_555 C(6) H(13) 3.59(3) ? . 1_655 C(6) H(20) 3.497 ? . 1_655 C(7) H(3) 3.522 ? . 1_554 C(7) H(5) 3.229 ? . 3_666 C(7) H(11) 3.59(4) ? . 4_555 C(7) H(12) 3.43(4) ? . 4_555 C(7) H(20) 3.270 ? . 3_566 C(8) H(11) 3.37(4) ? . 4_555 C(8) H(20) 3.235 ? . 3_566 C(9) H(17) 3.164 ? . 3_566 C(10) H(1) 3.160 ? . 4_555 C(10) H(4) 3.462 ? . 3_667 C(10) H(6) 3.348 ? . 1_556 C(11) H(11) 3.45(4) ? . 4_555 C(12) H(1) 3.401 ? . 4_555 C(12) H(12) 3.59(5) ? . 4_555 C(14) H(1) 3.243 ? . 4_555 C(14) H(6) 3.479 ? . 1_556 C(16) H(19) 3.554 ? . . H(1) C(4) 3.066 ? . 4_455 H(1) C(5) 3.395 ? . 4_455 H(1) C(10) 3.160 ? . 4_455 H(1) C(12) 3.401 ? . 4_455 H(1) C(14) 3.243 ? . 4_455 H(1) H(3) 2.770 ? . 4_455 H(1) H(4) 3.135 ? . 4_455 H(1) H(9) 2.621 ? . 4_455 H(2) Cl(1) 2.996 ? . 4_556 H(2) Cl(2) 3.368 ? . 4_556 H(2) O(1) 3.235 ? . 4_556 H(2) N(3) 3.593 ? . 4_556 H(2) H(11) 3.118 ? . 4_556 H(2) H(14) 3.588 ? . 4_555 H(2) H(16) 3.452 ? . 1_556 H(2) H(16) 3.578 ? . 4_556 H(2) H(15) 3.016 ? . 4_556 H(2) H(19) 3.090 ? . 4_556 H(2) H(20) 3.435 ? . 4_556 H(3) Cl(1) 2.906 ? . 1_656 H(3) C(2) 3.450 ? . 4_555 H(3) C(7) 3.522 ? . 1_556 H(3) H(1) 2.770 ? . 4_555 H(3) H(6) 3.035 ? . 1_556 H(3) H(11) 3.559 ? . 4_556 H(3) H(12) 3.559 ? . 4_556 H(3) H(16) 3.495 ? . 4_556 H(4) Cl(2) 2.876 ? . 1_656 H(4) C(10) 3.462 ? . 3_667 H(4) H(1) 3.135 ? . 4_555 H(4) H(10) 2.669 ? . 3_667 H(4) H(12) 3.558 ? . 4_555 H(4) H(13) 3.417 ? . 1_655 H(5) Cl(1) 3.355 ? . 1_655 H(5) O(1) 3.018 ? . 1_655 H(5) C(7) 3.229 ? . 3_666 H(5) H(6) 2.804 ? . 3_666 H(5) H(10) 3.427 ? . 3_667 H(5) H(12) 3.376 ? . 4_555 H(5) H(13) 3.095 ? . 1_655 H(5) H(18) 3.346 ? . 3_666 H(5) H(19) 3.448 ? . 1_655 H(5) H(20) 2.657 ? . 1_655 H(6) C(4) 3.357 ? . 1_554 H(6) C(6) 3.233 ? . 3_666 H(6) C(10) 3.348 ? . 1_554 H(6) C(14) 3.479 ? . 1_554 H(6) H(3) 3.035 ? . 1_554 H(6) H(5) 2.804 ? . 3_666 H(6) H(9) 3.187 ? . 1_554 H(6) H(10) 2.933 ? . 1_554 H(6) H(20) 3.568 ? . 1_655 H(6) H(20) 3.506 ? . 3_566 H(7) Cl(2) 2.787 ? . 3_566 H(7) N(4) 3.238 ? . 3_566 H(7) H(18) 3.352 ? . 3_566 H(7) H(17) 2.379 ? . 3_566 H(8) O(1) 3.431 ? . . H(8) N(4) 3.581 ? . 3_566 H(8) H(18) 3.354 ? . 3_566 H(8) H(17) 3.122 ? . 3_566 H(8) H(19) 2.916 ? . . H(9) C(2) 3.540 ? . 4_555 H(9) H(1) 2.621 ? . 4_555 H(9) H(6) 3.187 ? . 1_556 H(9) H(20) 3.109 ? . 1_656 H(10) Cl(2) 3.450 ? . 3_566 H(10) C(5) 3.060 ? . 3_667 H(10) C(6) 3.468 ? . 3_667 H(10) H(4) 2.669 ? . 3_667 H(10) H(5) 3.427 ? . 3_667 H(10) H(6) 2.933 ? . 1_556 H(11) Cl(1) 2.31(4) ? . . H(11) C(7) 3.59(4) ? . 4_455 H(11) C(8) 3.37(4) ? . 4_455 H(11) C(11) 3.45(4) ? . 4_455 H(11) H(2) 3.118 ? . 4_454 H(11) H(3) 3.559 ? . 4_454 H(11) H(16) 3.061 ? . 4_455 H(11) H(19) 3.573 ? . . H(12) Cl(1) 2.36(5) ? . 4_555 H(12) C(5) 3.22(4) ? . 4_455 H(12) C(6) 3.12(4) ? . 4_455 H(12) C(7) 3.43(4) ? . 4_455 H(12) C(12) 3.59(5) ? . 4_455 H(12) H(3) 3.559 ? . 4_454 H(12) H(4) 3.558 ? . 4_455 H(12) H(5) 3.376 ? . 4_455 H(12) H(13) 3.04(5) ? . 4_555 H(13) Cl(1) 2.36(4) ? . . H(13) Cl(2) 3.45(4) ? . 1_556 H(13) O(1) 3.26(4) ? . . H(13) C(6) 3.59(3) ? . 1_455 H(13) H(4) 3.417 ? . 1_455 H(13) H(5) 3.095 ? . 1_455 H(13) H(12) 3.04(5) ? . 4_455 H(13) H(19) 3.197 ? . . H(13) H(20) 3.544 ? . . H(14) Cl(2) 2.33(4) ? . 1_556 H(14) C(3) 3.54(4) ? . 4_455 H(14) H(2) 3.588 ? . 4_455 H(14) H(15) 2.98(4) ? . 1_556 H(18) O(1) 2.026 ? . 3_566 H(18) H(5) 3.346 ? . 3_666 H(18) H(7) 3.352 ? . 3_566 H(18) H(8) 3.354 ? . 3_566 H(18) H(19) 2.085 ? . 3_566 H(18) H(20) 2.300 ? . 3_566 H(16) Cl(1) 2.430 ? . 4_555 H(16) C(2) 3.592 ? . 1_554 H(16) C(3) 3.358 ? . 1_554 H(16) H(2) 3.452 ? . 1_554 H(16) H(2) 3.578 ? . 4_454 H(16) H(3) 3.495 ? . 4_454 H(16) H(11) 3.061 ? . 4_555 H(16) H(19) 3.575 ? . . H(17) Cl(2) 2.280 ? . . H(17) O(1) 3.430 ? . 3_566 H(17) C(9) 3.164 ? . 3_566 H(17) H(7) 2.379 ? . 3_566 H(17) H(8) 3.122 ? . 3_566 H(17) H(19) 3.419 ? . . H(17) H(19) 3.306 ? . 3_566 H(15) Cl(2) 2.32(2) ? . . H(15) O(1) 3.36(3) ? . . H(15) H(2) 3.016 ? . 4_454 H(15) H(14) 2.98(4) ? . 1_554 H(15) H(19) 2.920 ? . . H(19) Cl(1) 3.265 ? . . H(19) Cl(2) 3.116 ? . . H(19) O(1) 0.574 ? . . H(19) N(2) 3.508 ? . . H(19) N(3) 3.215 ? . . H(19) N(4) 2.816 ? . 3_566 H(19) C(16) 3.554 ? . . H(19) H(2) 3.090 ? . 4_454 H(19) H(5) 3.448 ? . 1_455 H(19) H(8) 2.916 ? . . H(19) H(11) 3.573 ? . . H(19) H(13) 3.197 ? . . H(19) H(18) 2.085 ? . 3_566 H(19) H(16) 3.575 ? . . H(19) H(17) 3.419 ? . . H(19) H(17) 3.306 ? . 3_566 H(19) H(15) 2.920 ? . . H(19) H(20) 1.314 ? . . H(20) Cl(1) 3.153 ? . . H(20) Cl(2) 3.307 ? . . H(20) O(1) 0.747 ? . . H(20) N(4) 3.059 ? . 3_566 H(20) C(6) 3.497 ? . 1_455 H(20) C(7) 3.270 ? . 3_566 H(20) C(8) 3.235 ? . 3_566 H(20) H(2) 3.435 ? . 4_454 H(20) H(5) 2.657 ? . 1_455 H(20) H(6) 3.568 ? . 1_455 H(20) H(6) 3.506 ? . 3_566 H(20) H(9) 3.109 ? . 1_454 H(20) H(13) 3.544 ? . . H(20) H(18) 2.300 ? . 3_566 H(20) H(19) 1.314 ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__Cytidine_(Rigaku_Master_f _database_code_depnum_ccdc_archive 'CCDC 920476' #TrackingRef '.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H14 Br2 N4 ' _chemical_formula_moiety 'C14 H14 Br2 N4 ' _chemical_formula_weight 398.10 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 9.3274(13) _cell_length_b 21.826(3) _cell_length_c 7.1188(9) _cell_angle_alpha 90.0000 _cell_angle_beta 94.249(11) _cell_angle_gamma 90.0000 _cell_volume 1445.3(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 25.1 _cell_measurement_theta_max 28.4 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.829 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784.00 _exptl_absorpt_coefficient_mu 7.079 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.151 _exptl_absorpt_correction_T_max 0.243 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 1789 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_theta_max 66.86 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 66.86 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 5 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -0.36 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1297 _reflns_number_gt 1215 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0997 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1297 _refine_ls_number_parameters 109 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0751P)^2^+0.5704P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.56 _refine_diff_density_min -1.42 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Br Br -0.676 1.280 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br(1) Br 0.0000 0.178479(17) 0.2500 0.0248(2) Uani 1.00 2 d S . . Br(2) Br 0.5000 0.15994(2) 0.2500 0.0401(2) Uani 1.00 2 d S . . N(1) N 0.6531(2) 0.30352(12) 0.3436(3) 0.0271(5) Uani 1.00 1 d . . . N(2) N 0.8152(2) 0.30536(12) 0.1188(3) 0.0271(5) Uani 1.00 1 d . . . C(1) C 0.7032(2) 0.40014(13) 0.1983(3) 0.0174(4) Uani 1.00 1 d . . . C(2) C 0.5789(2) 0.43193(12) 0.2276(3) 0.0169(4) Uani 1.00 1 d . . . C(3) C 0.5769(2) 0.49731(11) 0.2253(3) 0.0176(5) Uani 1.00 1 d . . . C(4) C 0.6917(2) 0.53262(12) 0.1867(3) 0.0205(5) Uani 1.00 1 d . . . C(5) C 0.8165(2) 0.49958(13) 0.1469(3) 0.0223(5) Uani 1.00 1 d . . . C(6) C 0.8223(2) 0.43719(13) 0.1523(3) 0.0212(5) Uani 1.00 1 d . . . C(7) C 0.7234(2) 0.33361(11) 0.2200(3) 0.0190(5) Uani 1.00 1 d . . . H(1) H 0.6882 0.5757 0.1866 0.025 Uiso 1.00 1 c R . . H(2) H 0.8983 0.5214 0.1156 0.027 Uiso 1.00 1 c R . . H(3) H 0.9081 0.4177 0.1246 0.025 Uiso 1.00 1 c R . . H(4) H 0.600(5) 0.321(2) 0.437(7) 0.050(12) Uiso 1.00 1 c . . . H(5) H 0.652(4) 0.269(2) 0.339(6) 0.045(11) Uiso 1.00 1 c . . . H(6) H 0.855(4) 0.3221(18) 0.033(6) 0.034(10) Uiso 1.00 1 c . . . H(7) H 0.845(4) 0.273(2) 0.146(5) 0.043(11) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.0268(2) 0.0179(2) 0.0303(2) 0.0000 0.00659(18) 0.0000 Br(2) 0.0502(3) 0.0238(3) 0.0503(3) 0.0000 0.0308(2) 0.0000 N(1) 0.0291(12) 0.0193(11) 0.0336(13) 0.0019(10) 0.0082(9) 0.0040(9) N(2) 0.0284(11) 0.0193(11) 0.0346(12) 0.0093(10) 0.0096(10) -0.0009(10) C(1) 0.0165(10) 0.0178(11) 0.0179(10) -0.0002(10) 0.0007(8) -0.0015(9) C(2) 0.0146(12) 0.0171(10) 0.0190(11) -0.0027(9) 0.0011(8) 0.0003(9) C(3) 0.0176(13) 0.0162(10) 0.0185(10) 0.0018(8) -0.0012(8) -0.0010(8) C(4) 0.0211(12) 0.0181(11) 0.0220(11) -0.0026(9) 0.0001(9) -0.0002(9) C(5) 0.0171(11) 0.0241(12) 0.0257(12) -0.0050(9) 0.0015(9) 0.0000(9) C(6) 0.0145(11) 0.0252(12) 0.0240(12) -0.0001(10) 0.0015(9) -0.0001(10) C(7) 0.0164(11) 0.0214(12) 0.0190(10) -0.0006(9) 0.0008(9) -0.0014(9) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N(1) C(7) 1.312(3) yes . . N(2) C(7) 1.313(3) yes . . C(1) C(2) 1.380(3) yes . . C(1) C(6) 1.432(3) yes . . C(1) C(7) 1.471(3) yes . . C(2) C(2) 1.529(3) yes . 2_655 C(2) C(3) 1.427(3) yes . . C(3) C(3) 1.503(3) yes . 2_655 C(3) C(4) 1.363(3) yes . . C(4) C(5) 1.416(3) yes . . C(5) C(6) 1.363(4) yes . . N(1) H(4) 0.94(5) no . . N(1) H(5) 0.75(4) no . . N(2) H(6) 0.83(4) no . . N(2) H(7) 0.78(4) no . . C(4) H(1) 0.940 no . . C(5) H(2) 0.940 no . . C(6) H(3) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(6) 115.2(2) yes . . . C(2) C(1) C(7) 125.7(2) yes . . . C(6) C(1) C(7) 119.1(2) yes . . . C(1) C(2) C(2) 149.8(2) yes . . 2_655 C(1) C(2) C(3) 120.7(2) yes . . . C(2) C(2) C(3) 89.47(19) yes 2_655 . . C(2) C(3) C(3) 90.51(18) yes . . 2_655 C(2) C(3) C(4) 123.9(2) yes . . . C(3) C(3) C(4) 145.6(2) yes 2_655 . . C(3) C(4) C(5) 115.0(2) yes . . . C(4) C(5) C(6) 122.3(2) yes . . . C(1) C(6) C(5) 122.7(2) yes . . . N(1) C(7) N(2) 120.8(2) yes . . . N(1) C(7) C(1) 119.9(2) yes . . . N(2) C(7) C(1) 119.3(2) yes . . . C(7) N(1) H(4) 125(2) no . . . C(7) N(1) H(5) 119(3) no . . . H(4) N(1) H(5) 116(4) no . . . C(7) N(2) H(6) 123(2) no . . . C(7) N(2) H(7) 121(3) no . . . H(6) N(2) H(7) 115(4) no . . . C(3) C(4) H(1) 122.5 no . . . C(5) C(4) H(1) 122.5 no . . . C(4) C(5) H(2) 118.8 no . . . C(6) C(5) H(2) 118.9 no . . . C(1) C(6) H(3) 118.6 no . . . C(5) C(6) H(3) 118.6 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(6) C(5) 3.2(3) ? . . . . C(6) C(1) C(2) C(3) -4.6(3) ? . . . . C(6) C(1) C(2) C(2) 178.4(3) ? . . . 2_655 C(2) C(1) C(7) N(1) -30.4(3) ? . . . . C(2) C(1) C(7) N(2) 151.5(2) ? . . . . C(7) C(1) C(2) C(3) 172.1(2) ? . . . . C(7) C(1) C(2) C(2) -4.9(5) ? . . . 2_655 C(6) C(1) C(7) N(1) 146.1(2) ? . . . . C(6) C(1) C(7) N(2) -31.9(3) ? . . . . C(7) C(1) C(6) C(5) -173.7(2) ? . . . . C(1) C(2) C(2) C(1) -6.8(7) ? . . 2_655 2_655 C(1) C(2) C(2) C(3) 175.8(3) ? . . 2_655 2_655 C(1) C(2) C(3) C(4) 3.1(3) ? . . . . C(1) C(2) C(3) C(3) -177.0(2) ? . . . 2_655 C(2) C(2) C(3) C(4) -178.5(2) ? 2_655 . . . C(2) C(2) C(3) C(3) 1.49(17) ? 2_655 . . 2_655 C(3) C(2) C(2) C(1) 175.8(3) ? . . 2_655 2_655 C(3) C(2) C(2) C(3) -1.57(18) ? . . 2_655 2_655 C(2) C(3) C(3) C(2) -1.60(18) ? . . 2_655 2_655 C(2) C(3) C(3) C(4) 178.3(3) ? . . 2_655 2_655 C(2) C(3) C(4) C(5) 0.3(3) ? . . . . C(3) C(3) C(4) C(5) -179.6(3) ? 2_655 . . . C(4) C(3) C(3) C(2) 178.3(3) ? . . 2_655 2_655 C(4) C(3) C(3) C(4) -1.7(6) ? . . 2_655 2_655 C(3) C(4) C(5) C(6) -1.8(3) ? . . . . C(4) C(5) C(6) C(1) 0.1(3) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Br(1) N(1) 3.343(2) ? . 7_556 Br(1) N(1) 3.343(2) ? . 8_454 Br(1) N(2) 3.358(2) ? . 1_455 Br(1) N(2) 3.358(2) ? . 2_655 Br(2) N(1) 3.488(2) ? . . Br(2) N(1) 3.488(2) ? . 2_655 Br(2) N(2) 3.333(2) ? . 7_655 Br(2) N(2) 3.333(2) ? . 8_455 N(1) Br(1) 3.343(2) ? . 7_556 N(1) Br(2) 3.488(2) ? . . N(1) N(1) 3.061(3) ? . 2_655 N(1) N(2) 2.282(3) ? . . N(1) C(1) 2.410(3) ? . . N(1) C(2) 2.989(3) ? . . N(1) C(2) 3.554(3) ? . 2_655 N(1) C(7) 3.568(3) ? . 2_655 N(2) Br(1) 3.358(2) ? . 1_655 N(2) Br(2) 3.333(2) ? . 7_655 N(2) N(1) 2.282(3) ? . . N(2) N(2) 3.142(3) ? . 7_655 N(2) C(1) 2.404(3) ? . . N(2) C(6) 2.888(3) ? . . C(1) N(1) 2.410(3) ? . . C(1) N(2) 2.404(3) ? . . C(1) C(2) 2.809(3) ? . 2_655 C(1) C(3) 2.440(3) ? . . C(1) C(3) 3.440(3) ? . 2_655 C(1) C(4) 2.894(3) ? . . C(1) C(5) 2.453(3) ? . . C(2) N(1) 2.989(3) ? . . C(2) N(1) 3.554(3) ? . 2_655 C(2) C(1) 2.809(3) ? . 2_655 C(2) C(3) 2.082(3) ? . 2_655 C(2) C(4) 2.463(3) ? . . C(2) C(4) 3.435(3) ? . 2_655 C(2) C(4) 3.447(3) ? . 4_565 C(2) C(5) 2.759(3) ? . . C(2) C(6) 2.374(3) ? . . C(2) C(7) 2.537(3) ? . . C(2) C(7) 3.585(3) ? . 2_655 C(3) C(1) 2.440(3) ? . . C(3) C(1) 3.440(3) ? . 2_655 C(3) C(2) 2.082(3) ? . 2_655 C(3) C(3) 3.418(3) ? . 3_665 C(3) C(3) 3.561(3) ? . 4_564 C(3) C(3) 3.561(3) ? . 4_565 C(3) C(4) 2.738(3) ? . 2_655 C(3) C(4) 3.441(3) ? . 4_565 C(3) C(5) 2.344(3) ? . . C(3) C(6) 2.721(3) ? . . C(4) C(1) 2.894(3) ? . . C(4) C(2) 2.463(3) ? . . C(4) C(2) 3.435(3) ? . 2_655 C(4) C(2) 3.447(3) ? . 4_564 C(4) C(3) 2.738(3) ? . 2_655 C(4) C(3) 3.441(3) ? . 4_564 C(4) C(5) 3.466(3) ? . 4_565 C(4) C(6) 2.435(3) ? . . C(4) C(6) 3.508(3) ? . 4_565 C(5) C(1) 2.453(3) ? . . C(5) C(2) 2.759(3) ? . . C(5) C(3) 2.344(3) ? . . C(5) C(4) 3.466(3) ? . 4_564 C(5) C(5) 3.559(3) ? . 4_564 C(5) C(5) 3.559(3) ? . 4_565 C(6) N(2) 2.888(3) ? . . C(6) C(2) 2.374(3) ? . . C(6) C(3) 2.721(3) ? . . C(6) C(4) 2.435(3) ? . . C(6) C(4) 3.508(3) ? . 4_564 C(6) C(6) 3.498(3) ? . 2_755 C(6) C(7) 2.502(3) ? . . C(7) N(1) 3.568(3) ? . 2_655 C(7) C(2) 2.537(3) ? . . C(7) C(2) 3.585(3) ? . 2_655 C(7) C(6) 2.502(3) ? . . Br(1) H(1) 2.905 ? . 5_445 Br(1) H(1) 2.905 ? . 6_545 Br(1) H(4) 2.48(5) ? . 7_556 Br(1) H(4) 2.48(5) ? . 8_454 Br(1) H(5) 3.53(4) ? . 7_556 Br(1) H(5) 3.53(4) ? . 8_454 Br(1) H(7) 2.59(4) ? . 1_455 Br(1) H(7) 2.59(4) ? . 2_655 Br(2) H(1) 3.443 ? . 5_445 Br(2) H(1) 3.443 ? . 6_645 Br(2) H(2) 3.289 ? . 5_445 Br(2) H(2) 3.289 ? . 6_645 Br(2) H(3) 3.325 ? . 7_655 Br(2) H(3) 3.325 ? . 8_455 Br(2) H(5) 2.82(4) ? . . Br(2) H(5) 2.82(4) ? . 2_655 Br(2) H(6) 2.54(4) ? . 7_655 Br(2) H(6) 2.54(4) ? . 8_455 Br(2) H(7) 3.58(4) ? . 7_655 Br(2) H(7) 3.58(4) ? . 8_455 N(1) H(1) 3.592 ? . 4_565 N(1) H(4) 3.00(4) ? . 2_655 N(1) H(5) 3.13(4) ? . 2_655 N(1) H(5) 3.21(4) ? . 7_656 N(1) H(6) 3.04(4) ? . . N(1) H(7) 2.45(4) ? . . N(2) H(3) 2.599 ? . . N(2) H(4) 3.15(5) ? . . N(2) H(5) 2.40(4) ? . . N(2) H(6) 3.34(4) ? . 7_655 N(2) H(7) 3.55(4) ? . 2_755 N(2) H(7) 2.88(4) ? . 7_655 C(1) H(1) 3.529 ? . 4_565 C(1) H(2) 3.290 ? . . C(1) H(3) 2.055 ? . . C(1) H(4) 2.65(4) ? . . C(1) H(4) 3.39(4) ? . 2_655 C(1) H(5) 3.08(4) ? . . C(1) H(6) 2.56(4) ? . . C(1) H(7) 3.11(4) ? . . C(2) H(1) 3.318 ? . . C(2) H(1) 3.354 ? . 4_565 C(2) H(3) 3.224 ? . . C(2) H(4) 2.83(4) ? . . C(2) H(4) 3.11(4) ? . 2_655 C(3) H(1) 2.029 ? . . C(3) H(1) 3.108 ? . 2_655 C(3) H(2) 3.196 ? . . C(4) H(2) 2.043 ? . . C(4) H(3) 3.271 ? . . C(5) H(1) 2.079 ? . . C(5) H(2) 3.082 ? . 2_755 C(5) H(2) 3.393 ? . 3_765 C(5) H(2) 3.398 ? . 4_565 C(5) H(3) 1.993 ? . . C(5) H(3) 3.438 ? . 2_755 C(6) H(1) 3.287 ? . . C(6) H(1) 3.467 ? . 4_564 C(6) H(2) 1.995 ? . . C(6) H(2) 3.502 ? . 2_755 C(6) H(2) 3.461 ? . 3_765 C(6) H(2) 3.442 ? . 4_565 C(6) H(3) 2.904 ? . 2_755 C(6) H(6) 2.68(4) ? . . C(6) H(7) 3.60(4) ? . . C(7) H(3) 2.640 ? . . C(7) H(4) 2.01(5) ? . . C(7) H(4) 3.15(4) ? . 2_655 C(7) H(5) 1.80(4) ? . . C(7) H(6) 1.90(4) ? . . C(7) H(7) 1.85(4) ? . . C(7) H(7) 3.51(4) ? . 7_655 H(1) Br(1) 2.905 ? . 5_555 H(1) Br(2) 3.443 ? . 5_555 H(1) N(1) 3.592 ? . 4_564 H(1) C(1) 3.529 ? . 4_564 H(1) C(2) 3.318 ? . . H(1) C(2) 3.354 ? . 4_564 H(1) C(3) 2.029 ? . . H(1) C(3) 3.108 ? . 2_655 H(1) C(5) 2.079 ? . . H(1) C(6) 3.287 ? . . H(1) C(6) 3.467 ? . 4_565 H(1) H(2) 2.376 ? . . H(1) H(4) 2.945 ? . 4_564 H(1) H(6) 3.593 ? . 4_565 H(2) Br(2) 3.289 ? . 5_555 H(2) C(1) 3.290 ? . . H(2) C(3) 3.196 ? . . H(2) C(4) 2.043 ? . . H(2) C(5) 3.082 ? . 2_755 H(2) C(5) 3.393 ? . 3_765 H(2) C(5) 3.398 ? . 4_564 H(2) C(6) 1.995 ? . . H(2) C(6) 3.502 ? . 2_755 H(2) C(6) 3.461 ? . 3_765 H(2) C(6) 3.442 ? . 4_564 H(2) H(1) 2.376 ? . . H(2) H(2) 2.593 ? . 2_755 H(2) H(2) 2.766 ? . 3_765 H(2) H(3) 2.267 ? . . H(2) H(3) 3.364 ? . 2_755 H(2) H(3) 2.900 ? . 3_765 H(3) Br(2) 3.325 ? . 7_655 H(3) N(2) 2.599 ? . . H(3) C(1) 2.055 ? . . H(3) C(2) 3.224 ? . . H(3) C(4) 3.271 ? . . H(3) C(5) 1.993 ? . . H(3) C(5) 3.438 ? . 2_755 H(3) C(6) 2.904 ? . 2_755 H(3) C(7) 2.640 ? . . H(3) H(2) 2.267 ? . . H(3) H(2) 3.364 ? . 2_755 H(3) H(2) 2.900 ? . 3_765 H(3) H(3) 2.382 ? . 2_755 H(3) H(6) 2.231 ? . . H(3) H(7) 3.225 ? . . H(4) Br(1) 2.48(5) ? . 7_556 H(4) N(1) 3.00(4) ? . 2_655 H(4) N(2) 3.15(5) ? . . H(4) C(1) 2.65(4) ? . . H(4) C(1) 3.39(4) ? . 2_655 H(4) C(2) 2.83(4) ? . . H(4) C(2) 3.11(4) ? . 2_655 H(4) C(7) 2.01(5) ? . . H(4) C(7) 3.15(4) ? . 2_655 H(4) H(1) 2.945 ? . 4_565 H(4) H(4) 3.13(6) ? . 2_655 H(4) H(5) 1.44(6) ? . . H(4) H(5) 3.16(6) ? . 2_655 H(4) H(5) 3.35(6) ? . 7_656 H(4) H(7) 3.36(6) ? . . H(4) H(7) 3.56(6) ? . 8_455 H(5) Br(1) 3.53(4) ? . 7_556 H(5) Br(2) 2.82(4) ? . . H(5) N(1) 3.13(4) ? . 2_655 H(5) N(1) 3.21(4) ? . 7_656 H(5) N(2) 2.40(4) ? . . H(5) C(1) 3.08(4) ? . . H(5) C(7) 1.80(4) ? . . H(5) H(4) 1.44(6) ? . . H(5) H(4) 3.16(6) ? . 2_655 H(5) H(4) 3.35(6) ? . 7_656 H(5) H(5) 3.01(6) ? . 2_655 H(5) H(5) 2.95(6) ? . 7_656 H(5) H(6) 3.21(6) ? . . H(5) H(6) 3.31(6) ? . 7_655 H(5) H(7) 2.34(6) ? . . H(5) H(7) 3.57(6) ? . 7_655 H(6) Br(2) 2.54(4) ? . 7_655 H(6) N(1) 3.04(4) ? . . H(6) N(2) 3.34(4) ? . 7_655 H(6) C(1) 2.56(4) ? . . H(6) C(6) 2.68(4) ? . . H(6) C(7) 1.90(4) ? . . H(6) H(1) 3.593 ? . 4_564 H(6) H(3) 2.231 ? . . H(6) H(5) 3.21(6) ? . . H(6) H(5) 3.31(6) ? . 7_655 H(6) H(7) 1.36(6) ? . . H(6) H(7) 3.00(6) ? . 7_655 H(7) Br(1) 2.59(4) ? . 1_655 H(7) Br(2) 3.58(4) ? . 7_655 H(7) N(1) 2.45(4) ? . . H(7) N(2) 3.55(4) ? . 2_755 H(7) N(2) 2.88(4) ? . 7_655 H(7) C(1) 3.11(4) ? . . H(7) C(6) 3.60(4) ? . . H(7) C(7) 1.85(4) ? . . H(7) C(7) 3.51(4) ? . 7_655 H(7) H(3) 3.225 ? . . H(7) H(4) 3.36(6) ? . . H(7) H(4) 3.56(6) ? . 8_554 H(7) H(5) 2.34(6) ? . . H(7) H(5) 3.57(6) ? . 7_655 H(7) H(6) 1.36(6) ? . . H(7) H(6) 3.00(6) ? . 7_655 H(7) H(7) 3.15(6) ? . 2_755 H(7) H(7) 2.81(5) ? . 7_655 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__kusu063 _database_code_depnum_ccdc_archive 'CCDC 920477' #TrackingRef '16979_web_deposit_cif_file_0_TakahiroKusukawa_1358505716.1c.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H20 Cl2 N4 O2 ' _chemical_formula_moiety 'C16 H20 Cl2 N4 O2 ' _chemical_formula_weight 371.27 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 22.853(5) _cell_length_b 7.5764(14) _cell_length_c 10.434(2) _cell_angle_alpha 90.0000 _cell_angle_beta 96.625(17) _cell_angle_gamma 90.0000 _cell_volume 1794.6(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 22 _cell_measurement_theta_min 25.1 _cell_measurement_theta_max 29.0 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776.00 _exptl_absorpt_coefficient_mu 3.396 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.515 _exptl_absorpt_correction_T_max 0.712 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 4309 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_theta_max 66.79 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 66.79 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -10.56 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3183 _reflns_number_gt 2830 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1547 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3183 _refine_ls_number_parameters 248 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1322P)^2^+0.0460P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.60 _refine_diff_density_min -0.31 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.364 0.702 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl(1) Cl 0.160535(18) 0.78652(7) 0.68245(5) 0.0386(2) Uani 1.00 1 d . . . Cl(2) Cl 0.158039(18) 0.99042(7) 0.17320(4) 0.0359(2) Uani 1.00 1 d . . . O(1) O 0.20082(7) 1.00961(19) 0.46727(16) 0.0396(3) Uiso 1.00 1 d . . . O(2) O 0.11459(7) 0.7136(2) 0.95410(16) 0.0512(4) Uiso 1.00 1 d . . . N(1) N 0.18161(8) 0.4056(2) 0.92125(17) 0.0380(4) Uani 1.00 1 d . . . N(2) N 0.20406(7) 0.1626(2) 0.80761(17) 0.0378(4) Uani 1.00 1 d . . . N(3) N 0.22120(7) 0.3686(2) 0.43597(16) 0.0357(4) Uani 1.00 1 d . . . N(4) N 0.20412(9) 0.6165(2) 0.3154(2) 0.0436(4) Uani 1.00 1 d . . . C(1) C 0.10216(7) 0.2433(2) 0.80306(18) 0.0280(4) Uani 1.00 1 d . . . C(2) C 0.06670(9) 0.1862(2) 0.89114(19) 0.0358(4) Uani 1.00 1 d . . . C(3) C 0.00750(9) 0.1391(3) 0.8524(2) 0.0403(4) Uani 1.00 1 d . . . C(4) C -0.01509(8) 0.1504(2) 0.7263(2) 0.0360(4) Uani 1.00 1 d . . . C(5) C 0.00263(9) 0.3329(3) 0.2827(2) 0.0393(4) Uani 1.00 1 d . . . C(6) C 0.03304(10) 0.4065(3) 0.19337(18) 0.0432(5) Uani 1.00 1 d . . . C(7) C 0.09247(10) 0.4570(3) 0.2269(2) 0.0395(4) Uani 1.00 1 d . . . C(8) C 0.12026(8) 0.4339(2) 0.34951(18) 0.0306(4) Uani 1.00 1 d . . . C(9) C 0.11246(7) 0.3378(2) 0.57763(17) 0.0261(3) Uani 1.00 1 d . . . C(10) C -0.00440(8) 0.2378(2) 0.50440(19) 0.0320(4) Uani 1.00 1 d . . . C(11) C 0.07924(7) 0.2653(2) 0.66927(17) 0.0250(3) Uani 1.00 1 d . . . C(12) C 0.01939(7) 0.2156(2) 0.63183(19) 0.0296(4) Uani 1.00 1 d . . . C(13) C 0.08883(7) 0.3589(2) 0.44892(16) 0.0270(3) Uani 1.00 1 d . . . C(14) C 0.02890(8) 0.3088(2) 0.41219(18) 0.0310(4) Uani 1.00 1 d . . . C(15) C 0.16593(8) 0.2727(2) 0.84540(17) 0.0289(4) Uani 1.00 1 d . . . C(16) C 0.18396(8) 0.4755(2) 0.36956(19) 0.0324(4) Uani 1.00 1 d . . . H(1) H 0.0818 0.1781 0.9786 0.043 Uiso 1.00 1 c R . . H(2) H -0.0164 0.0997 0.9142 0.048 Uiso 1.00 1 c R . . H(3) H -0.0541 0.1146 0.7013 0.043 Uiso 1.00 1 c R . . H(4) H -0.0365 0.2969 0.2594 0.047 Uiso 1.00 1 c R . . H(5) H 0.0149 0.4243 0.1089 0.052 Uiso 1.00 1 c R . . H(6) H 0.1134 0.5075 0.1637 0.047 Uiso 1.00 1 c R . . H(7) H 0.1515 0.3731 0.6032 0.031 Uiso 1.00 1 c R . . H(8) H -0.0437 0.2046 0.4794 0.038 Uiso 1.00 1 c R . . H(9) H 0.2236(12) 0.419(3) 0.963(2) 0.055(7) Uiso 1.00 1 c . . . H(10) H 0.1567(13) 0.487(4) 0.931(3) 0.059(8) Uiso 1.00 1 c . . . H(11) H 0.2385(16) 0.188(4) 0.816(3) 0.068(9) Uiso 1.00 1 c . . . H(12) H 0.1921(9) 0.058(3) 0.762(2) 0.035(5) Uiso 1.00 1 c . . . H(13) H 0.2087(10) 0.268(3) 0.459(2) 0.039(6) Uiso 1.00 1 c . . . H(14) H 0.2591(10) 0.394(2) 0.4361(19) 0.028(4) Uiso 1.00 1 c . . . H(15) H 0.1737(14) 0.698(4) 0.270(3) 0.071(9) Uiso 1.00 1 c . . . H(16) H 0.2437(12) 0.636(3) 0.318(2) 0.041(6) Uiso 1.00 1 c . . . H(17) H 0.185(2) 0.937(8) 0.522(5) 0.150(19) Uiso 1.00 1 c . . . H(18) H 0.1848(18) 0.997(5) 0.369(4) 0.100(13) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(1) 0.0271(3) 0.0445(3) 0.0446(3) -0.00350(17) 0.0052(2) 0.00229(19) Cl(2) 0.0253(3) 0.0478(3) 0.0342(3) 0.00271(16) 0.0020(2) 0.00214(17) N(1) 0.0312(8) 0.0429(10) 0.0389(9) -0.0019(7) -0.0007(6) -0.0051(7) N(2) 0.0191(8) 0.0468(10) 0.0459(9) 0.0024(6) -0.0023(6) -0.0067(7) N(3) 0.0239(8) 0.0395(9) 0.0449(9) -0.0009(6) 0.0085(6) 0.0088(7) N(4) 0.0386(10) 0.0377(9) 0.0577(10) 0.0015(7) 0.0198(8) 0.0105(8) C(1) 0.0211(8) 0.0317(8) 0.0312(9) 0.0013(6) 0.0037(6) -0.0005(7) C(2) 0.0315(9) 0.0444(10) 0.0322(9) 0.0072(8) 0.0063(7) 0.0083(7) C(3) 0.0296(9) 0.0488(11) 0.0452(11) 0.0019(8) 0.0152(8) 0.0139(9) C(4) 0.0190(8) 0.0403(10) 0.0495(11) -0.0021(7) 0.0073(7) 0.0058(8) C(5) 0.0316(9) 0.0459(11) 0.0372(10) 0.0056(8) -0.0101(7) -0.0041(8) C(6) 0.0475(11) 0.0518(12) 0.0280(9) 0.0108(9) -0.0049(8) 0.0015(8) C(7) 0.0469(11) 0.0427(11) 0.0295(9) 0.0090(9) 0.0072(8) 0.0053(8) C(8) 0.0284(9) 0.0317(9) 0.0324(9) 0.0041(7) 0.0065(7) 0.0007(7) C(9) 0.0171(7) 0.0307(8) 0.0302(8) -0.0004(6) 0.0017(6) -0.0004(6) C(10) 0.0159(7) 0.0380(10) 0.0408(10) -0.0022(6) -0.0024(6) -0.0009(7) C(11) 0.0186(7) 0.0274(8) 0.0290(8) 0.0021(6) 0.0022(6) -0.0003(6) C(12) 0.0196(8) 0.0312(9) 0.0382(9) 0.0009(6) 0.0040(6) 0.0006(7) C(13) 0.0217(8) 0.0299(8) 0.0291(8) 0.0030(6) 0.0022(6) -0.0018(6) C(14) 0.0256(8) 0.0349(9) 0.0311(9) 0.0038(7) -0.0028(6) -0.0024(7) C(15) 0.0241(8) 0.0377(9) 0.0237(8) -0.0007(6) -0.0021(6) 0.0052(6) C(16) 0.0323(9) 0.0345(9) 0.0323(9) 0.0020(7) 0.0120(7) 0.0005(7) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N(1) C(15) 1.305(2) yes . . N(2) C(15) 1.300(2) yes . . N(3) C(16) 1.313(2) yes . . N(4) C(16) 1.316(2) yes . . C(1) C(2) 1.364(2) yes . . C(1) C(11) 1.443(2) yes . . C(1) C(15) 1.490(2) yes . . C(2) C(3) 1.412(2) yes . . C(3) C(4) 1.360(2) yes . . C(4) C(12) 1.420(2) yes . . C(5) C(6) 1.346(3) yes . . C(5) C(14) 1.425(2) yes . . C(6) C(7) 1.416(3) yes . . C(7) C(8) 1.372(2) yes . . C(8) C(13) 1.444(2) yes . . C(8) C(16) 1.481(2) yes . . C(9) C(11) 1.400(2) yes . . C(9) C(13) 1.398(2) yes . . C(10) C(12) 1.387(2) yes . . C(10) C(14) 1.401(2) yes . . C(11) C(12) 1.429(2) yes . . C(13) C(14) 1.430(2) yes . . N(1) H(9) 1.01(2) no . . N(1) H(10) 0.85(3) no . . N(2) H(11) 0.80(3) no . . N(2) H(12) 0.95(2) no . . N(4) H(15) 1.01(3) no . . N(4) H(16) 0.91(2) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.940 no . . C(10) H(8) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(11) 120.72(15) yes . . . C(2) C(1) C(15) 118.98(16) yes . . . C(11) C(1) C(15) 120.20(15) yes . . . C(1) C(2) C(3) 120.76(17) yes . . . C(2) C(3) C(4) 120.33(19) yes . . . C(3) C(4) C(12) 120.99(17) yes . . . C(6) C(5) C(14) 120.99(18) yes . . . C(5) C(6) C(7) 119.84(17) yes . . . C(6) C(7) C(8) 121.60(19) yes . . . C(7) C(8) C(13) 120.30(17) yes . . . C(7) C(8) C(16) 116.51(18) yes . . . C(13) C(8) C(16) 123.00(15) yes . . . C(11) C(9) C(13) 121.42(14) yes . . . C(12) C(10) C(14) 121.39(16) yes . . . C(1) C(11) C(9) 122.76(14) yes . . . C(1) C(11) C(12) 117.60(16) yes . . . C(9) C(11) C(12) 119.61(15) yes . . . C(4) C(12) C(10) 121.34(15) yes . . . C(4) C(12) C(11) 119.49(16) yes . . . C(10) C(12) C(11) 119.13(17) yes . . . C(8) C(13) C(9) 124.47(14) yes . . . C(8) C(13) C(14) 116.88(14) yes . . . C(9) C(13) C(14) 118.61(15) yes . . . C(5) C(14) C(10) 119.82(16) yes . . . C(5) C(14) C(13) 120.36(17) yes . . . C(10) C(14) C(13) 119.81(16) yes . . . N(1) C(15) N(2) 122.15(17) yes . . . N(1) C(15) C(1) 119.08(17) yes . . . N(2) C(15) C(1) 118.75(16) yes . . . N(3) C(16) N(4) 119.30(17) yes . . . N(3) C(16) C(8) 120.66(17) yes . . . N(4) C(16) C(8) 119.97(17) yes . . . H(17) O(1) H(18) 117(4) no . . . C(15) N(1) H(9) 121.4(16) no . . . C(15) N(1) H(10) 119(2) no . . . H(9) N(1) H(10) 119(2) no . . . C(15) N(2) H(11) 120(2) no . . . C(15) N(2) H(12) 121.6(14) no . . . H(11) N(2) H(12) 118(2) no . . . C(16) N(3) H(13) 118.6(16) no . . . C(16) N(3) H(14) 116.1(13) no . . . H(13) N(3) H(14) 123(2) no . . . C(16) N(4) H(15) 116.3(19) no . . . C(16) N(4) H(16) 120.9(15) no . . . H(15) N(4) H(16) 123(2) no . . . C(1) C(2) H(1) 119.6 no . . . C(3) C(2) H(1) 119.6 no . . . C(2) C(3) H(2) 119.8 no . . . C(4) C(3) H(2) 119.8 no . . . C(3) C(4) H(3) 119.5 no . . . C(12) C(4) H(3) 119.5 no . . . C(6) C(5) H(4) 119.5 no . . . C(14) C(5) H(4) 119.5 no . . . C(5) C(6) H(5) 120.1 no . . . C(7) C(6) H(5) 120.1 no . . . C(6) C(7) H(6) 119.2 no . . . C(8) C(7) H(6) 119.2 no . . . C(11) C(9) H(7) 119.3 no . . . C(13) C(9) H(7) 119.3 no . . . C(12) C(10) H(8) 119.3 no . . . C(14) C(10) H(8) 119.3 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(11) C(9) 174.33(18) ? . . . . C(2) C(1) C(11) C(12) -3.5(2) ? . . . . C(11) C(1) C(2) C(3) 3.1(2) ? . . . . C(2) C(1) C(15) N(1) -70.4(2) ? . . . . C(2) C(1) C(15) N(2) 108.1(2) ? . . . . C(15) C(1) C(2) C(3) -173.35(18) ? . . . . C(11) C(1) C(15) N(1) 113.2(2) ? . . . . C(11) C(1) C(15) N(2) -68.3(2) ? . . . . C(15) C(1) C(11) C(9) -9.3(2) ? . . . . C(15) C(1) C(11) C(12) 172.90(16) ? . . . . C(1) C(2) C(3) C(4) -0.1(2) ? . . . . C(2) C(3) C(4) C(12) -2.3(3) ? . . . . C(3) C(4) C(12) C(10) -175.97(19) ? . . . . C(3) C(4) C(12) C(11) 1.8(2) ? . . . . C(6) C(5) C(14) C(10) 177.7(2) ? . . . . C(6) C(5) C(14) C(13) -1.4(3) ? . . . . C(14) C(5) C(6) C(7) 1.6(3) ? . . . . C(5) C(6) C(7) C(8) -0.4(3) ? . . . . C(6) C(7) C(8) C(13) -0.9(3) ? . . . . C(6) C(7) C(8) C(16) 174.21(19) ? . . . . C(7) C(8) C(13) C(9) -176.91(18) ? . . . . C(7) C(8) C(13) C(14) 1.1(2) ? . . . . C(7) C(8) C(16) N(3) -135.1(2) ? . . . . C(7) C(8) C(16) N(4) 41.6(2) ? . . . . C(13) C(8) C(16) N(3) 39.9(2) ? . . . . C(13) C(8) C(16) N(4) -143.36(19) ? . . . . C(16) C(8) C(13) C(9) 8.3(2) ? . . . . C(16) C(8) C(13) C(14) -173.77(17) ? . . . . C(11) C(9) C(13) C(8) 179.50(16) ? . . . . C(11) C(9) C(13) C(14) 1.6(2) ? . . . . C(13) C(9) C(11) C(1) -179.39(16) ? . . . . C(13) C(9) C(11) C(12) -1.6(2) ? . . . . C(12) C(10) C(14) C(5) -178.77(18) ? . . . . C(12) C(10) C(14) C(13) 0.3(2) ? . . . . C(14) C(10) C(12) C(4) 177.39(18) ? . . . . C(14) C(10) C(12) C(11) -0.4(2) ? . . . . C(1) C(11) C(12) C(4) 1.1(2) ? . . . . C(1) C(11) C(12) C(10) 178.88(17) ? . . . . C(9) C(11) C(12) C(4) -176.81(17) ? . . . . C(9) C(11) C(12) C(10) 1.0(2) ? . . . . C(8) C(13) C(14) C(5) 0.1(2) ? . . . . C(8) C(13) C(14) C(10) -179.00(17) ? . . . . C(9) C(13) C(14) C(5) 178.18(17) ? . . . . C(9) C(13) C(14) C(10) -0.9(2) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Cl(1) O(1) 3.0369(17) ? . . Cl(1) O(2) 3.1826(18) ? . . Cl(1) N(2) 3.2428(19) ? . 1_565 Cl(1) N(2) 3.2238(16) ? . 2_556 Cl(2) O(1) 3.1145(16) ? . . Cl(2) O(2) 3.1761(16) ? . 1_554 Cl(2) N(3) 3.2389(17) ? . 2_555 Cl(2) N(4) 3.3133(19) ? . . Cl(2) N(4) 3.281(2) ? . 2_555 O(1) Cl(1) 3.0369(17) ? . . O(1) Cl(2) 3.1145(16) ? . . O(1) N(1) 2.911(2) ? . 2_556 O(1) N(3) 2.785(2) ? . 1_565 O(1) N(4) 3.379(2) ? . . O(1) C(9) 3.482(2) ? . 1_565 O(2) Cl(1) 3.1826(18) ? . . O(2) Cl(2) 3.1761(16) ? . 1_556 O(2) N(1) 2.834(2) ? . . O(2) C(5) 3.447(2) ? . 3_566 O(2) C(7) 3.532(2) ? . 1_556 N(1) O(1) 2.911(2) ? . 2_546 N(1) O(2) 2.834(2) ? . . N(2) Cl(1) 3.2428(19) ? . 1_545 N(2) Cl(1) 3.2238(16) ? . 2_546 N(3) Cl(2) 3.2389(17) ? . 2_545 N(3) O(1) 2.785(2) ? . 1_545 N(4) Cl(2) 3.3133(19) ? . . N(4) Cl(2) 3.281(2) ? . 2_545 N(4) O(1) 3.379(2) ? . . C(3) C(6) 3.583(3) ? . 3_566 C(4) C(6) 3.496(3) ? . 3_566 C(4) C(7) 3.523(3) ? . 3_566 C(5) O(2) 3.447(2) ? . 3_566 C(5) C(12) 3.585(2) ? . 3_566 C(6) C(3) 3.583(3) ? . 3_566 C(6) C(4) 3.496(3) ? . 3_566 C(7) O(2) 3.532(2) ? . 1_554 C(7) C(4) 3.523(3) ? . 3_566 C(9) O(1) 3.482(2) ? . 1_545 C(12) C(5) 3.585(2) ? . 3_566 Cl(1) H(4) 3.033 ? . 3_566 Cl(1) H(7) 3.240 ? . . Cl(1) H(8) 2.991 ? . 3_566 Cl(1) H(9) 3.35(3) ? . 2_556 Cl(1) H(10) 3.46(3) ? . . Cl(1) H(11) 2.43(3) ? . 2_556 Cl(1) H(12) 2.30(2) ? . 1_565 Cl(1) H(17) 2.16(6) ? . . Cl(2) H(1) 2.891 ? . 1_564 Cl(2) H(2) 3.331 ? . 3_566 Cl(2) H(3) 2.950 ? . 3_566 Cl(2) H(14) 2.43(2) ? . 2_555 Cl(2) H(15) 2.44(3) ? . . Cl(2) H(16) 3.56(2) ? . . Cl(2) H(16) 2.49(2) ? . 2_555 Cl(2) H(18) 2.06(4) ? . . O(1) H(7) 3.352 ? . 1_565 O(1) H(9) 1.92(2) ? . 2_556 O(1) H(10) 3.31(3) ? . 2_556 O(1) H(11) 3.50(3) ? . 2_556 O(1) H(12) 3.13(2) ? . 1_565 O(1) H(13) 1.97(2) ? . 1_565 O(1) H(14) 3.23(2) ? . 1_565 O(1) H(15) 3.14(3) ? . . O(1) H(16) 3.43(2) ? . . O(1) H(16) 3.50(2) ? . 2_555 O(1) H(17) 0.89(6) ? . . O(1) H(18) 1.05(4) ? . . O(2) H(2) 3.105 ? . 3_567 O(2) H(4) 2.690 ? . 3_566 O(2) H(5) 3.135 ? . 3_566 O(2) H(6) 2.690 ? . 1_556 O(2) H(9) 3.34(2) ? . . O(2) H(10) 2.00(3) ? . . O(2) H(14) 3.28(2) ? . 2_556 O(2) H(15) 3.42(3) ? . 1_556 N(1) H(6) 3.215 ? . 1_556 N(1) H(17) 3.04(5) ? . 2_546 N(2) H(14) 3.39(2) ? . 2_546 N(2) H(17) 3.42(5) ? . 1_545 N(2) H(17) 3.59(5) ? . 2_546 N(3) H(11) 3.58(3) ? . 2_556 N(3) H(13) 0.86(2) ? . . N(3) H(14) 0.89(2) ? . . N(3) H(16) 3.35(2) ? . 2_545 N(3) H(17) 3.51(6) ? . 1_545 N(3) H(18) 2.99(4) ? . 1_545 N(4) H(9) 3.53(2) ? . 2_556 N(4) H(13) 3.03(2) ? . . N(4) H(14) 2.37(2) ? . . N(4) H(14) 3.54(2) ? . 2_555 N(4) H(17) 3.31(6) ? . . N(4) H(18) 2.98(4) ? . . N(4) H(18) 3.48(4) ? . 2_545 C(2) H(2) 3.267 ? . 3_557 C(2) H(5) 3.232 ? . 1_556 C(2) H(5) 3.490 ? . 3_566 C(3) H(2) 3.022 ? . 3_557 C(3) H(4) 3.590 ? . 3_556 C(3) H(5) 3.429 ? . 1_556 C(3) H(5) 3.378 ? . 3_566 C(4) H(4) 3.586 ? . 3_556 C(5) H(3) 3.586 ? . 3_556 C(6) H(1) 3.136 ? . 1_554 C(6) H(5) 3.463 ? . 3_565 C(7) H(1) 3.331 ? . 1_554 C(7) H(3) 3.466 ? . 3_566 C(7) H(10) 3.57(3) ? . 1_554 C(8) H(13) 2.54(2) ? . . C(8) H(14) 3.21(2) ? . . C(9) H(13) 2.70(2) ? . . C(9) H(17) 3.54(6) ? . 1_545 C(10) H(8) 3.525 ? . 3_556 C(11) H(4) 3.561 ? . 3_566 C(12) H(8) 3.455 ? . 3_556 C(13) H(8) 3.569 ? . 3_566 C(13) H(13) 2.82(2) ? . . C(14) H(3) 3.490 ? . 3_556 C(16) H(13) 1.88(2) ? . . C(16) H(14) 1.88(2) ? . . H(1) Cl(2) 2.891 ? . 1_546 H(1) C(6) 3.136 ? . 1_556 H(1) C(7) 3.331 ? . 1_556 H(1) H(2) 2.881 ? . 3_557 H(1) H(5) 2.855 ? . 1_556 H(1) H(6) 3.188 ? . 1_556 H(2) Cl(2) 3.331 ? . 3_566 H(2) O(2) 3.105 ? . 3_567 H(2) C(2) 3.267 ? . 3_557 H(2) C(3) 3.022 ? . 3_557 H(2) H(1) 2.881 ? . 3_557 H(2) H(2) 2.396 ? . 3_557 H(2) H(5) 3.218 ? . 1_556 H(3) Cl(2) 2.950 ? . 3_566 H(3) C(5) 3.586 ? . 3_556 H(3) C(7) 3.466 ? . 3_566 H(3) C(14) 3.490 ? . 3_556 H(3) H(6) 3.529 ? . 3_566 H(3) H(15) 3.123 ? . 3_566 H(3) H(17) 3.597 ? . 3_566 H(3) H(18) 3.111 ? . 3_566 H(4) Cl(1) 3.033 ? . 3_566 H(4) O(2) 2.690 ? . 3_566 H(4) C(3) 3.590 ? . 3_556 H(4) C(4) 3.586 ? . 3_556 H(4) C(11) 3.561 ? . 3_566 H(4) H(10) 3.596 ? . 3_566 H(5) O(2) 3.135 ? . 3_566 H(5) C(2) 3.232 ? . 1_554 H(5) C(2) 3.490 ? . 3_566 H(5) C(3) 3.429 ? . 1_554 H(5) C(3) 3.378 ? . 3_566 H(5) C(6) 3.463 ? . 3_565 H(5) H(1) 2.855 ? . 1_554 H(5) H(2) 3.218 ? . 1_554 H(5) H(5) 2.566 ? . 3_565 H(6) O(2) 2.690 ? . 1_554 H(6) N(1) 3.215 ? . 1_554 H(6) H(1) 3.188 ? . 1_554 H(6) H(3) 3.529 ? . 3_566 H(6) H(9) 3.521 ? . 1_554 H(6) H(10) 2.728 ? . 1_554 H(7) Cl(1) 3.240 ? . . H(7) O(1) 3.352 ? . 1_545 H(7) H(11) 3.495 ? . 2_556 H(7) H(13) 2.254 ? . . H(7) H(14) 3.178 ? . . H(7) H(17) 3.517 ? . 1_545 H(8) Cl(1) 2.991 ? . 3_566 H(8) C(10) 3.525 ? . 3_556 H(8) C(12) 3.455 ? . 3_556 H(8) C(13) 3.569 ? . 3_566 H(8) H(17) 3.408 ? . 3_566 H(9) Cl(1) 3.35(3) ? . 2_546 H(9) O(1) 1.92(2) ? . 2_546 H(9) O(2) 3.34(2) ? . . H(9) N(4) 3.53(2) ? . 2_546 H(9) H(6) 3.521 ? . 1_556 H(9) H(12) 3.37(3) ? . 2_556 H(9) H(13) 3.12(4) ? . 2_556 H(9) H(16) 3.16(3) ? . 2_546 H(9) H(17) 2.07(6) ? . 2_546 H(9) H(18) 2.64(5) ? . 2_546 H(10) Cl(1) 3.46(3) ? . . H(10) O(1) 3.31(3) ? . 2_546 H(10) O(2) 2.00(3) ? . . H(10) C(7) 3.57(3) ? . 1_556 H(10) H(4) 3.596 ? . 3_566 H(10) H(6) 2.728 ? . 1_556 H(11) Cl(1) 2.43(3) ? . 2_546 H(11) O(1) 3.50(3) ? . 2_546 H(11) N(3) 3.58(3) ? . 2_546 H(11) H(7) 3.495 ? . 2_546 H(11) H(12) 3.37(4) ? . 2_556 H(11) H(14) 3.40(4) ? . 2_546 H(11) H(17) 2.97(6) ? . 2_546 H(12) Cl(1) 2.30(2) ? . 1_545 H(12) O(1) 3.13(2) ? . 1_545 H(12) H(9) 3.37(3) ? . 2_546 H(12) H(11) 3.37(4) ? . 2_546 H(12) H(14) 3.45(3) ? . 2_546 H(12) H(17) 2.66(6) ? . 1_545 H(13) O(1) 1.97(2) ? . 1_545 H(13) N(3) 0.86(2) ? . . H(13) N(4) 3.03(2) ? . . H(13) C(8) 2.54(2) ? . . H(13) C(9) 2.70(2) ? . . H(13) C(13) 2.82(2) ? . . H(13) C(16) 1.88(2) ? . . H(13) H(7) 2.254 ? . . H(13) H(9) 3.12(4) ? . 2_546 H(13) H(14) 1.54(3) ? . . H(13) H(16) 3.29(3) ? . . H(13) H(16) 3.35(3) ? . 2_545 H(13) H(17) 2.66(7) ? . 1_545 H(13) H(18) 2.29(5) ? . 1_545 H(14) Cl(2) 2.43(2) ? . 2_545 H(14) O(1) 3.23(2) ? . 1_545 H(14) O(2) 3.28(2) ? . 2_546 H(14) N(2) 3.39(2) ? . 2_556 H(14) N(3) 0.89(2) ? . . H(14) N(4) 2.37(2) ? . . H(14) N(4) 3.54(2) ? . 2_545 H(14) C(8) 3.21(2) ? . . H(14) C(16) 1.88(2) ? . . H(14) H(7) 3.178 ? . . H(14) H(11) 3.40(4) ? . 2_556 H(14) H(12) 3.45(3) ? . 2_556 H(14) H(13) 1.54(3) ? . . H(14) H(15) 3.37(3) ? . . H(14) H(15) 3.16(4) ? . 2_545 H(14) H(16) 2.21(3) ? . . H(14) H(16) 3.29(3) ? . 2_545 H(14) H(18) 3.48(4) ? . 1_545 H(15) Cl(2) 2.44(3) ? . . H(15) O(1) 3.14(3) ? . . H(15) O(2) 3.42(3) ? . 1_554 H(15) H(3) 3.123 ? . 3_566 H(15) H(14) 3.37(3) ? . . H(15) H(14) 3.16(4) ? . 2_555 H(15) H(17) 3.17(6) ? . . H(15) H(18) 2.49(5) ? . . H(16) Cl(2) 3.56(2) ? . . H(16) Cl(2) 2.49(2) ? . 2_545 H(16) O(1) 3.43(2) ? . . H(16) O(1) 3.50(2) ? . 2_545 H(16) N(3) 3.35(2) ? . 2_555 H(16) H(9) 3.16(3) ? . 2_556 H(16) H(13) 3.29(3) ? . . H(16) H(13) 3.35(3) ? . 2_555 H(16) H(14) 2.21(3) ? . . H(16) H(14) 3.29(3) ? . 2_555 H(16) H(17) 3.49(6) ? . . H(16) H(18) 3.12(4) ? . . H(16) H(18) 2.88(5) ? . 2_545 H(17) Cl(1) 2.16(6) ? . . H(17) O(1) 0.89(6) ? . . H(17) N(1) 3.04(5) ? . 2_556 H(17) N(2) 3.42(5) ? . 1_565 H(17) N(2) 3.59(5) ? . 2_556 H(17) N(3) 3.51(6) ? . 1_565 H(17) N(4) 3.31(6) ? . . H(17) C(9) 3.54(6) ? . 1_565 H(17) H(3) 3.597 ? . 3_566 H(17) H(7) 3.517 ? . 1_565 H(17) H(8) 3.408 ? . 3_566 H(17) H(9) 2.07(6) ? . 2_556 H(17) H(11) 2.97(6) ? . 2_556 H(17) H(12) 2.66(6) ? . 1_565 H(17) H(13) 2.66(7) ? . 1_565 H(17) H(15) 3.17(6) ? . . H(17) H(16) 3.49(6) ? . . H(17) H(18) 1.66(7) ? . . H(18) Cl(2) 2.06(4) ? . . H(18) O(1) 1.05(4) ? . . H(18) N(3) 2.99(4) ? . 1_565 H(18) N(4) 2.98(4) ? . . H(18) N(4) 3.48(4) ? . 2_555 H(18) H(3) 3.111 ? . 3_566 H(18) H(9) 2.64(4) ? . 2_556 H(18) H(13) 2.29(5) ? . 1_565 H(18) H(14) 3.48(4) ? . 1_565 H(18) H(15) 2.49(5) ? . . H(18) H(16) 3.12(4) ? . . H(18) H(16) 2.88(5) ? . 2_555 H(18) H(17) 1.66(7) ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__kusu043 _database_code_depnum_ccdc_archive 'CCDC 920478' #TrackingRef '16980_web_deposit_cif_file_0_TakahiroKusukawa_1358506190.1a2_2a2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H30 N4 O8 ' _chemical_formula_moiety 'C24 H30 N4 O8 ' _chemical_formula_weight 502.52 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.677(3) _cell_length_b 11.8984(14) _cell_length_c 9.9909(12) _cell_angle_alpha 103.393(9) _cell_angle_beta 108.395(12) _cell_angle_gamma 89.725(13) _cell_volume 1277.9(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25.0 _cell_measurement_theta_max 29.0 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532.00 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_correction_T_max 0.847 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 6152 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_theta_max 66.75 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 66.75 _diffrn_measured_fraction_theta_full 0.986 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -1.90 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4465 _reflns_number_gt 3016 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.2094 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4465 _refine_ls_number_parameters 366 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0977P)^2^+1.0174P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.99 _refine_diff_density_min -0.78 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 0.6692(2) 0.3566(2) 0.6002(3) 0.0562(6) Uani 1.00 1 d . . . O(2) O 0.6270(2) 0.5198(2) 0.7277(3) 0.0598(7) Uani 1.00 1 d . . . O(3) O 1.2597(2) 0.5984(2) 0.7767(2) 0.0509(6) Uani 1.00 1 d . . . O(4) O 1.2359(2) 0.7243(2) 0.9641(2) 0.0608(7) Uani 1.00 1 d . . . O(5) O 0.5805(3) 0.0069(2) 0.3070(3) 0.0919(10) Uani 1.00 1 d . . . O(6) O 0.3652(6) 0.0181(2) 0.4020(4) 0.171(2) Uani 1.00 1 d . . . O(7) O 0.3009(2) -0.2154(2) 0.6439(3) 0.0680(7) Uani 1.00 1 d . . . O(8) O 0.2460(3) -0.1819(2) 0.2441(3) 0.0678(8) Uani 1.00 1 d . . . N(1) N 0.4909(2) 0.3249(2) 1.1146(3) 0.0543(8) Uani 1.00 1 d . . . N(2) N 0.5271(2) 0.1724(2) 0.9527(3) 0.0541(8) Uani 1.00 1 d . . . N(3) N 0.3818(2) 0.4310(2) 0.6244(3) 0.0452(6) Uani 1.00 1 d . . . N(4) N 0.4283(2) 0.2614(2) 0.4991(3) 0.0515(7) Uani 1.00 1 d . . . C(1) C 0.3285(2) 0.1788(2) 0.9783(3) 0.0384(7) Uani 1.00 1 d . . . C(2) C 0.3053(3) 0.1035(3) 1.0552(3) 0.0515(8) Uani 1.00 1 d . . . C(3) C 0.1889(3) 0.0557(3) 1.0200(4) 0.0557(9) Uani 1.00 1 d . . . C(4) C 0.0968(3) 0.0825(2) 0.9080(4) 0.0499(8) Uani 1.00 1 d . . . C(5) C -0.0025(3) 0.1680(2) 0.4418(4) 0.0500(8) Uani 1.00 1 d . . . C(6) C 0.0401(3) 0.1853(2) 0.3338(3) 0.0531(9) Uani 1.00 1 d . . . C(7) C 0.1557(3) 0.2358(2) 0.3687(3) 0.0459(7) Uani 1.00 1 d . . . C(8) C 0.2268(2) 0.2713(2) 0.5147(3) 0.0375(6) Uani 1.00 1 d . . . C(9) C 0.2576(2) 0.2918(2) 0.7839(3) 0.0419(7) Uani 1.00 1 d . . . C(10) C 0.0217(2) 0.1873(3) 0.7070(4) 0.0517(8) Uani 1.00 1 d . . . C(11) C 0.2369(2) 0.2072(2) 0.8660(3) 0.0384(6) Uani 1.00 1 d . . . C(12) C 0.1190(2) 0.1573(2) 0.8299(3) 0.0408(7) Uani 1.00 1 d . . . C(13) C 0.1845(2) 0.2559(2) 0.6245(3) 0.0382(6) Uani 1.00 1 d . . . C(14) C 0.0675(2) 0.2029(2) 0.5871(3) 0.0446(7) Uani 1.00 1 d . . . C(15) C 0.4553(2) 0.2281(2) 1.0167(3) 0.0390(6) Uani 1.00 1 d . . . C(16) C 0.3513(2) 0.3239(2) 0.5476(3) 0.0392(7) Uani 1.00 1 d . . . C(17) C 0.8306(2) 0.4998(2) 0.7338(3) 0.0394(7) Uani 1.00 1 d . . . C(18) C 0.9023(2) 0.4602(2) 0.6479(3) 0.0431(7) Uani 1.00 1 d . . . C(19) C 1.0209(2) 0.5043(2) 0.6888(3) 0.0408(7) Uani 1.00 1 d . . . C(20) C 1.0714(2) 0.5874(2) 0.8183(3) 0.0363(6) Uani 1.00 1 d . . . C(21) C 1.0004(2) 0.6250(2) 0.9066(3) 0.0420(7) Uani 1.00 1 d . . . C(22) C 0.8811(3) 0.5819(2) 0.8644(3) 0.0443(7) Uani 1.00 1 d . . . C(23) C 0.6992(3) 0.4560(2) 0.6845(3) 0.0453(7) Uani 1.00 1 d . . . C(24) C 1.1989(2) 0.6395(2) 0.8569(3) 0.0384(6) Uani 1.00 1 d . . . H(1) H 0.3682 0.0850 1.1308 0.062 Uiso 1.00 1 c R . . H(2) H 0.1723 0.0050 1.0721 0.067 Uiso 1.00 1 c R . . H(3) H 0.0178 0.0495 0.8846 0.060 Uiso 1.00 1 c R . . H(4) H -0.0804 0.1318 0.4166 0.060 Uiso 1.00 1 c R . . H(5) H -0.0095 0.1629 0.2361 0.064 Uiso 1.00 1 c R . . H(6) H 0.1859 0.2460 0.2952 0.055 Uiso 1.00 1 c R . . H(7) H 0.3437 0.2982 0.7942 0.050 Uiso 1.00 1 c R . . H(8) H 0.2357 0.3683 0.8264 0.050 Uiso 1.00 1 c R . . H(9) H -0.0118 0.2590 0.7441 0.062 Uiso 1.00 1 c R . . H(10) H -0.0438 0.1256 0.6674 0.062 Uiso 1.00 1 c R . . H(11) H 0.8700 0.4029 0.5610 0.052 Uiso 1.00 1 c R . . H(12) H 1.0678 0.4778 0.6284 0.049 Uiso 1.00 1 c R . . H(13) H 1.0338 0.6800 0.9955 0.050 Uiso 1.00 1 c R . . H(14) H 0.8338 0.6085 0.9244 0.053 Uiso 1.00 1 c R . . H(15) H 0.445(4) 0.367(4) 1.155(4) 0.079(14) Uiso 1.00 1 c . . . H(16) H 0.581(4) 0.354(3) 1.154(4) 0.080(13) Uiso 1.00 1 c . . . H(17) H 0.493(4) 0.113(4) 0.873(5) 0.087(15) Uiso 1.00 1 c . . . H(18) H 0.608(3) 0.202(3) 0.975(4) 0.056(10) Uiso 1.00 1 c . . . H(19) H 0.326(3) 0.477(3) 0.652(3) 0.050(9) Uiso 1.00 1 c . . . H(20) H 0.473(4) 0.464(4) 0.656(5) 0.085(14) Uiso 1.00 1 c . . . H(21) H 0.414(4) 0.187(4) 0.460(4) 0.073(13) Uiso 1.00 1 c . . . H(22) H 0.519(4) 0.301(4) 0.535(5) 0.085(14) Uiso 1.00 1 c . . . H(23) H 0.242(4) -0.213(4) 0.159(5) 0.076(14) Uiso 1.00 1 c . . . H(24) H 0.297(8) -0.221(8) 0.300(10) 0.20(4) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0421(13) 0.0409(12) 0.0776(17) -0.0084(10) 0.0243(12) -0.0083(11) O(2) 0.0388(13) 0.0503(13) 0.0813(18) -0.0017(10) 0.0258(12) -0.0102(12) O(3) 0.0338(11) 0.0558(13) 0.0520(13) -0.0053(10) 0.0146(10) -0.0092(10) O(4) 0.0409(13) 0.0668(16) 0.0572(15) -0.0131(11) 0.0158(11) -0.0188(12) O(5) 0.112(2) 0.074(2) 0.0664(18) -0.0326(18) 0.0221(18) -0.0191(15) O(6) 0.324(7) 0.0418(18) 0.085(2) -0.017(2) -0.011(3) 0.0044(17) O(7) 0.0646(17) 0.0670(17) 0.0693(17) -0.0071(13) 0.0224(14) 0.0088(13) O(8) 0.079(2) 0.0573(16) 0.0583(17) -0.0077(14) 0.0251(15) -0.0075(14) N(1) 0.0315(15) 0.0515(17) 0.0608(18) -0.0026(12) 0.0105(13) -0.0171(14) N(2) 0.0341(15) 0.0563(18) 0.0555(17) -0.0087(13) 0.0128(13) -0.0158(14) N(3) 0.0405(15) 0.0359(13) 0.0541(16) -0.0031(12) 0.0172(13) -0.0017(11) N(4) 0.0421(16) 0.0359(15) 0.072(2) -0.0026(12) 0.0243(14) -0.0034(13) C(1) 0.0323(15) 0.0395(15) 0.0382(15) -0.0005(12) 0.0108(12) 0.0000(12) C(2) 0.0474(19) 0.056(2) 0.0502(19) 0.0023(16) 0.0136(16) 0.0147(16) C(3) 0.055(2) 0.058(2) 0.060(2) -0.0028(17) 0.0211(18) 0.0209(17) C(4) 0.0417(18) 0.0445(18) 0.064(2) -0.0060(14) 0.0224(16) 0.0054(15) C(5) 0.0319(16) 0.0459(18) 0.058(2) -0.0032(13) -0.0012(15) 0.0067(15) C(6) 0.0453(19) 0.0457(18) 0.0468(19) -0.0010(15) -0.0080(15) 0.0017(14) C(7) 0.0442(18) 0.0412(16) 0.0442(17) 0.0041(14) 0.0072(14) 0.0049(13) C(8) 0.0312(15) 0.0308(14) 0.0438(16) 0.0020(11) 0.0070(12) 0.0032(12) C(9) 0.0290(15) 0.0466(17) 0.0439(17) -0.0110(12) 0.0050(13) 0.0082(13) C(10) 0.0296(16) 0.060(2) 0.062(2) -0.0054(14) 0.0107(15) 0.0138(17) C(11) 0.0330(15) 0.0364(15) 0.0397(15) -0.0028(12) 0.0099(12) -0.0001(12) C(12) 0.0291(15) 0.0403(15) 0.0491(17) -0.0040(12) 0.0125(13) 0.0031(13) C(13) 0.0276(14) 0.0350(14) 0.0443(16) -0.0005(11) 0.0041(12) 0.0053(12) C(14) 0.0294(15) 0.0428(17) 0.0519(19) -0.0017(13) 0.0025(13) 0.0074(14) C(15) 0.0309(15) 0.0413(15) 0.0360(15) 0.0019(12) 0.0037(12) 0.0025(12) C(16) 0.0395(17) 0.0331(14) 0.0420(16) -0.0007(12) 0.0114(13) 0.0056(12) C(17) 0.0340(16) 0.0356(15) 0.0474(17) 0.0015(12) 0.0131(13) 0.0082(13) C(18) 0.0352(16) 0.0387(16) 0.0466(17) -0.0023(13) 0.0109(13) -0.0034(13) C(19) 0.0326(15) 0.0426(16) 0.0430(16) 0.0026(12) 0.0140(13) 0.0001(13) C(20) 0.0313(15) 0.0369(15) 0.0382(15) 0.0031(12) 0.0082(12) 0.0084(12) C(21) 0.0366(16) 0.0451(16) 0.0371(15) -0.0020(13) 0.0084(13) 0.0011(12) C(22) 0.0419(17) 0.0475(17) 0.0454(17) 0.0020(14) 0.0215(14) 0.0045(13) C(23) 0.0394(17) 0.0402(16) 0.0558(19) -0.0016(13) 0.0200(15) 0.0039(14) C(24) 0.0312(15) 0.0406(15) 0.0373(15) 0.0014(12) 0.0069(12) 0.0034(12) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SIR2002 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(23) 1.260(3) yes . . O(2) C(23) 1.243(4) yes . . O(3) C(24) 1.249(4) yes . . O(4) C(24) 1.251(3) yes . . N(1) C(15) 1.297(3) yes . . N(2) C(15) 1.298(4) yes . . N(3) C(16) 1.311(3) yes . . N(4) C(16) 1.303(4) yes . . C(1) C(2) 1.386(5) yes . . C(1) C(11) 1.389(4) yes . . C(1) C(15) 1.493(4) yes . . C(2) C(3) 1.380(5) yes . . C(3) C(4) 1.383(5) yes . . C(4) C(12) 1.385(5) yes . . C(5) C(6) 1.378(6) yes . . C(5) C(14) 1.387(4) yes . . C(6) C(7) 1.386(5) yes . . C(7) C(8) 1.396(4) yes . . C(8) C(13) 1.385(5) yes . . C(8) C(16) 1.492(4) yes . . C(9) C(11) 1.501(5) yes . . C(9) C(13) 1.510(4) yes . . C(10) C(12) 1.498(4) yes . . C(10) C(14) 1.504(6) yes . . C(11) C(12) 1.405(4) yes . . C(13) C(14) 1.407(4) yes . . C(17) C(18) 1.387(5) yes . . C(17) C(22) 1.391(3) yes . . C(17) C(23) 1.510(4) yes . . C(18) C(19) 1.381(4) yes . . C(19) C(20) 1.390(3) yes . . C(20) C(21) 1.393(5) yes . . C(20) C(24) 1.511(4) yes . . C(21) C(22) 1.385(4) yes . . O(8) H(23) 0.83(5) no . . O(8) H(24) 0.89(10) no . . N(1) H(15) 0.86(5) no . . N(1) H(16) 1.03(4) no . . N(2) H(17) 0.92(4) no . . N(2) H(18) 0.95(4) no . . N(3) H(19) 0.92(4) no . . N(3) H(20) 1.06(5) no . . N(4) H(21) 0.87(4) no . . N(4) H(22) 1.08(5) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.980 no . . C(9) H(8) 0.980 no . . C(10) H(9) 0.980 no . . C(10) H(10) 0.980 no . . C(18) H(11) 0.940 no . . C(19) H(12) 0.940 no . . C(21) H(13) 0.940 no . . C(22) H(14) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(11) 121.3(3) yes . . . C(2) C(1) C(15) 118.6(2) yes . . . C(11) C(1) C(15) 120.1(3) yes . . . C(1) C(2) C(3) 119.5(3) yes . . . C(2) C(3) C(4) 120.0(4) yes . . . C(3) C(4) C(12) 121.0(3) yes . . . C(6) C(5) C(14) 121.1(3) yes . . . C(5) C(6) C(7) 120.2(3) yes . . . C(6) C(7) C(8) 119.0(3) yes . . . C(7) C(8) C(13) 121.4(2) yes . . . C(7) C(8) C(16) 117.4(3) yes . . . C(13) C(8) C(16) 121.3(2) yes . . . C(11) C(9) C(13) 112.2(2) yes . . . C(12) C(10) C(14) 112.4(2) yes . . . C(1) C(11) C(9) 122.9(2) yes . . . C(1) C(11) C(12) 118.8(3) yes . . . C(9) C(11) C(12) 118.2(2) yes . . . C(4) C(12) C(10) 122.5(2) yes . . . C(4) C(12) C(11) 119.3(2) yes . . . C(10) C(12) C(11) 118.2(3) yes . . . C(8) C(13) C(9) 123.6(2) yes . . . C(8) C(13) C(14) 118.9(2) yes . . . C(9) C(13) C(14) 117.4(3) yes . . . C(5) C(14) C(10) 122.0(3) yes . . . C(5) C(14) C(13) 119.3(3) yes . . . C(10) C(14) C(13) 118.7(2) yes . . . N(1) C(15) N(2) 121.9(3) yes . . . N(1) C(15) C(1) 118.8(3) yes . . . N(2) C(15) C(1) 119.3(2) yes . . . N(3) C(16) N(4) 121.1(3) yes . . . N(3) C(16) C(8) 120.1(3) yes . . . N(4) C(16) C(8) 118.8(2) yes . . . C(18) C(17) C(22) 118.9(2) yes . . . C(18) C(17) C(23) 120.4(2) yes . . . C(22) C(17) C(23) 120.7(3) yes . . . C(17) C(18) C(19) 120.7(2) yes . . . C(18) C(19) C(20) 120.7(3) yes . . . C(19) C(20) C(21) 118.7(2) yes . . . C(19) C(20) C(24) 119.8(3) yes . . . C(21) C(20) C(24) 121.4(2) yes . . . C(20) C(21) C(22) 120.5(2) yes . . . C(17) C(22) C(21) 120.5(3) yes . . . O(1) C(23) O(2) 123.9(3) yes . . . O(1) C(23) C(17) 117.5(3) yes . . . O(2) C(23) C(17) 118.6(2) yes . . . O(3) C(24) O(4) 123.6(3) yes . . . O(3) C(24) C(20) 118.2(2) yes . . . O(4) C(24) C(20) 118.1(3) yes . . . H(23) O(8) H(24) 107(7) no . . . C(15) N(1) H(15) 125(2) no . . . C(15) N(1) H(16) 120(2) no . . . H(15) N(1) H(16) 115(3) no . . . C(15) N(2) H(17) 118(3) no . . . C(15) N(2) H(18) 121(2) no . . . H(17) N(2) H(18) 120(4) no . . . C(16) N(3) H(19) 121(2) no . . . C(16) N(3) H(20) 119(2) no . . . H(19) N(3) H(20) 120(3) no . . . C(16) N(4) H(21) 123(3) no . . . C(16) N(4) H(22) 115(2) no . . . H(21) N(4) H(22) 120(4) no . . . C(1) C(2) H(1) 120.3 no . . . C(3) C(2) H(1) 120.3 no . . . C(2) C(3) H(2) 120.0 no . . . C(4) C(3) H(2) 120.0 no . . . C(3) C(4) H(3) 119.5 no . . . C(12) C(4) H(3) 119.5 no . . . C(6) C(5) H(4) 119.4 no . . . C(14) C(5) H(4) 119.4 no . . . C(5) C(6) H(5) 119.9 no . . . C(7) C(6) H(5) 119.9 no . . . C(6) C(7) H(6) 120.5 no . . . C(8) C(7) H(6) 120.5 no . . . C(11) C(9) H(7) 109.2 no . . . C(11) C(9) H(8) 109.2 no . . . C(13) C(9) H(7) 109.2 no . . . C(13) C(9) H(8) 109.2 no . . . H(7) C(9) H(8) 107.9 no . . . C(12) C(10) H(9) 109.1 no . . . C(12) C(10) H(10) 109.1 no . . . C(14) C(10) H(9) 109.1 no . . . C(14) C(10) H(10) 109.1 no . . . H(9) C(10) H(10) 107.9 no . . . C(17) C(18) H(11) 119.7 no . . . C(19) C(18) H(11) 119.7 no . . . C(18) C(19) H(12) 119.6 no . . . C(20) C(19) H(12) 119.6 no . . . C(20) C(21) H(13) 119.8 no . . . C(22) C(21) H(13) 119.8 no . . . C(17) C(22) H(14) 119.7 no . . . C(21) C(22) H(14) 119.7 no . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__kusu045 _database_code_depnum_ccdc_archive 'CCDC 920479' #TrackingRef '16981_web_deposit_cif_file_0_TakahiroKusukawa_1358506330.1a2_2b2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H24 F4 N4 O7 ' _chemical_formula_moiety 'C24 H24 F4 N4 O7 ' _chemical_formula_weight 556.47 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.4606(7) _cell_length_b 12.5728(12) _cell_length_c 10.4779(8) _cell_angle_alpha 108.785(6) _cell_angle_beta 102.511(6) _cell_angle_gamma 63.700(6) _cell_volume 1276.52(17) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25.2 _cell_measurement_theta_max 29.1 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576.00 _exptl_absorpt_coefficient_mu 1.097 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.621 _exptl_absorpt_correction_T_max 0.803 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 6221 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_theta_max 66.86 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 66.86 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 2.06 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4537 _reflns_number_gt 3913 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1536 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4537 _refine_ls_number_parameters 378 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0757P)^2^+1.2190P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 0.73 _refine_diff_density_min -0.52 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.073 0.053 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 F(1) F 1.52408(13) 0.38998(12) 0.90839(14) 0.0312(3) Uani 1.00 1 d . . . F(2) F 1.77307(13) 0.30042(13) 0.86715(15) 0.0349(3) Uani 1.00 1 d . . . F(3) F 1.67113(15) 0.55208(15) 0.57509(16) 0.0434(3) Uani 1.00 1 d . . . F(4) F 1.42132(14) 0.65309(13) 0.62618(15) 0.0372(3) Uani 1.00 1 d . . . O(1) O 1.26445(16) 0.70096(15) 0.83559(17) 0.0308(3) Uani 1.00 1 d . . . O(2) O 1.27104(16) 0.51330(16) 0.7954(2) 0.0380(4) Uani 1.00 1 d . . . O(3) O 1.94142(18) 0.41713(18) 0.7423(2) 0.0515(5) Uani 1.00 1 d . . . O(4) O 1.90874(16) 0.25182(16) 0.61633(19) 0.0365(4) Uani 1.00 1 d . . . O(5) O 2.09820(18) -0.04700(17) 0.29908(19) 0.0405(4) Uiso 1.00 1 d . . . O(6) O 1.1902(2) 0.9248(2) 1.0493(2) 0.0450(4) Uiso 1.00 1 d . . . O(7) O 1.13955(19) 0.85524(18) 0.6605(2) 0.0443(4) Uiso 1.00 1 d . . . N(1) N 0.8382(2) 0.8468(2) 0.4892(2) 0.0305(4) Uani 1.00 1 d . . . N(2) N 0.8142(2) 0.6750(2) 0.3543(2) 0.0348(4) Uani 1.00 1 d . . . N(3) N 0.9716(2) 0.8167(2) 0.9155(2) 0.0351(4) Uani 1.00 1 d . . . N(4) N 1.0148(2) 0.6133(2) 0.8616(2) 0.0393(5) Uani 1.00 1 d . . . C(1) C 0.6338(2) 0.8244(2) 0.4804(2) 0.0241(4) Uani 1.00 1 d . . . C(2) C 0.5379(2) 0.8161(2) 0.3743(2) 0.0291(5) Uani 1.00 1 d . . . C(3) C 0.4131(2) 0.8446(2) 0.4013(2) 0.0294(5) Uani 1.00 1 d . . . C(4) C 0.3843(2) 0.8777(2) 0.5337(2) 0.0272(4) Uani 1.00 1 d . . . C(5) C 0.5512(2) 0.7866(2) 0.9511(2) 0.0309(5) Uani 1.00 1 d . . . C(6) C 0.6594(2) 0.7133(2) 1.0190(2) 0.0333(5) Uani 1.00 1 d . . . C(7) C 0.7832(2) 0.6982(2) 1.0023(2) 0.0315(5) Uani 1.00 1 d . . . C(8) C 0.7986(2) 0.7539(2) 0.9157(2) 0.0254(4) Uani 1.00 1 d . . . C(9) C 0.7009(2) 0.8758(2) 0.7363(2) 0.0285(4) Uani 1.00 1 d . . . C(10) C 0.4501(2) 0.9204(2) 0.7853(2) 0.0316(5) Uani 1.00 1 d . . . C(11) C 0.6903(2) 0.8247(2) 0.8433(2) 0.0245(4) Uani 1.00 1 d . . . C(12) C 0.5647(2) 0.8429(2) 0.8642(2) 0.0274(4) Uani 1.00 1 d . . . C(13) C 0.6041(2) 0.86265(19) 0.6148(2) 0.0234(4) Uani 1.00 1 d . . . C(14) C 0.4782(2) 0.8873(2) 0.6399(2) 0.0255(4) Uani 1.00 1 d . . . C(15) C 0.7680(2) 0.7815(2) 0.4412(2) 0.0254(4) Uani 1.00 1 d . . . C(16) C 0.9344(2) 0.7279(2) 0.8962(2) 0.0263(4) Uani 1.00 1 d . . . C(17) C 1.4624(2) 0.52874(19) 0.7716(2) 0.0231(4) Uani 1.00 1 d . . . C(18) C 1.5563(2) 0.4355(2) 0.8276(2) 0.0236(4) Uani 1.00 1 d . . . C(19) C 1.6860(2) 0.3871(2) 0.8047(2) 0.0250(4) Uani 1.00 1 d . . . C(20) C 1.7292(2) 0.4227(2) 0.7198(2) 0.0255(4) Uani 1.00 1 d . . . C(21) C 1.6364(2) 0.5140(2) 0.6614(2) 0.0275(4) Uani 1.00 1 d . . . C(22) C 1.5066(2) 0.5659(2) 0.6878(2) 0.0257(4) Uani 1.00 1 d . . . C(23) C 1.3200(2) 0.5866(2) 0.8031(2) 0.0246(4) Uani 1.00 1 d . . . C(24) C 1.8724(2) 0.3591(2) 0.6896(2) 0.0283(5) Uani 1.00 1 d . . . H(1) H 0.5583 0.7911 0.2842 0.035 Uiso 1.00 1 c R . . H(2) H 0.3480 0.8416 0.3298 0.035 Uiso 1.00 1 c R . . H(3) H 0.3004 0.8937 0.5518 0.033 Uiso 1.00 1 c R . . H(4) H 0.4672 0.7985 0.9641 0.037 Uiso 1.00 1 c R . . H(5) H 0.6490 0.6741 1.0758 0.040 Uiso 1.00 1 c R . . H(6) H 0.8569 0.6501 1.0496 0.038 Uiso 1.00 1 c R . . H(7) H 0.7897 0.8323 0.7075 0.034 Uiso 1.00 1 c R . . H(8) H 0.6844 0.9628 0.7746 0.034 Uiso 1.00 1 c R . . H(9) H 0.4318 1.0074 0.8269 0.038 Uiso 1.00 1 c R . . H(10) H 0.3725 0.9074 0.7881 0.038 Uiso 1.00 1 c R . . H(11) H 0.804(2) 0.924(2) 0.541(3) 0.036(7) Uiso 1.00 1 c . . . H(12) H 0.921(3) 0.814(3) 0.456(3) 0.056(9) Uiso 1.00 1 c . . . H(13) H 0.895(3) 0.647(2) 0.331(3) 0.047(8) Uiso 1.00 1 c . . . H(14) H 0.764(3) 0.631(3) 0.326(3) 0.064(10) Uiso 1.00 1 c . . . H(15) H 0.919(3) 0.891(3) 0.944(2) 0.036(7) Uiso 1.00 1 c . . . H(16) H 1.050(3) 0.797(3) 0.900(3) 0.063(10) Uiso 1.00 1 c . . . H(17) H 1.093(3) 0.594(3) 0.842(3) 0.059(9) Uiso 1.00 1 c . . . H(19) H 1.178(3) 0.917(2) 1.111(3) 0.042(8) Uiso 1.00 1 c . . . H(20) H 1.241(4) 0.841(4) 0.985(4) 0.094(14) Uiso 1.00 1 c . . . H(18) H 0.982(3) 0.555(3) 0.838(3) 0.059(10) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0317(7) 0.0323(7) 0.0369(7) -0.0133(5) 0.0118(5) 0.0118(5) F(2) 0.0258(6) 0.0320(7) 0.0440(8) -0.0028(5) 0.0061(5) 0.0170(6) F(3) 0.0416(8) 0.0500(9) 0.0520(9) -0.0171(7) 0.0181(7) 0.0230(7) F(4) 0.0310(7) 0.0377(7) 0.0444(8) -0.0067(6) 0.0050(6) 0.0217(6) O(1) 0.0269(8) 0.0261(8) 0.0351(8) -0.0067(6) 0.0087(6) 0.0045(6) O(2) 0.0242(8) 0.0330(9) 0.0573(11) -0.0152(7) 0.0137(7) 0.0001(8) O(3) 0.0286(9) 0.0406(10) 0.0794(14) -0.0210(8) 0.0224(9) -0.0136(10) O(4) 0.0278(8) 0.0301(9) 0.0472(10) -0.0109(7) 0.0148(7) -0.0021(7) N(1) 0.0235(9) 0.0282(10) 0.0405(11) -0.0133(8) 0.0111(8) 0.0004(8) N(2) 0.0241(10) 0.0345(11) 0.0431(12) -0.0147(9) 0.0129(8) -0.0040(9) N(3) 0.0252(10) 0.0349(12) 0.0500(13) -0.0173(9) 0.0011(9) 0.0108(10) N(4) 0.0232(10) 0.0340(12) 0.0606(14) -0.0134(9) 0.0137(9) 0.0028(10) C(1) 0.0211(10) 0.0229(10) 0.0297(11) -0.0109(8) 0.0041(8) 0.0044(8) C(2) 0.0259(11) 0.0318(12) 0.0275(11) -0.0127(9) 0.0033(9) 0.0027(9) C(3) 0.0227(10) 0.0304(11) 0.0333(12) -0.0127(9) -0.0016(9) 0.0056(9) C(4) 0.0169(9) 0.0276(11) 0.0375(12) -0.0092(8) 0.0029(8) 0.0082(9) C(5) 0.0256(11) 0.0407(13) 0.0291(11) -0.0185(10) 0.0102(9) 0.0000(10) C(6) 0.0354(13) 0.0427(13) 0.0297(11) -0.0214(11) 0.0093(9) 0.0070(10) C(7) 0.0290(12) 0.0362(12) 0.0314(11) -0.0155(10) 0.0047(9) 0.0068(10) C(8) 0.0223(10) 0.0266(11) 0.0277(10) -0.0131(9) 0.0067(8) -0.0000(8) C(9) 0.0232(10) 0.0366(12) 0.0295(11) -0.0168(9) 0.0018(8) 0.0069(9) C(10) 0.0199(10) 0.0384(13) 0.0327(12) -0.0100(9) 0.0083(9) 0.0031(10) C(11) 0.0213(10) 0.0274(11) 0.0252(10) -0.0132(8) 0.0058(8) -0.0000(8) C(12) 0.0223(10) 0.0322(12) 0.0255(10) -0.0133(9) 0.0064(8) -0.0014(9) C(13) 0.0197(10) 0.0227(10) 0.0285(11) -0.0105(8) 0.0025(8) 0.0045(8) C(14) 0.0212(10) 0.0233(10) 0.0312(11) -0.0087(8) 0.0052(8) 0.0047(8) C(15) 0.0227(10) 0.0278(11) 0.0277(10) -0.0109(9) 0.0039(8) 0.0077(9) C(16) 0.0223(10) 0.0311(12) 0.0271(10) -0.0137(9) 0.0019(8) 0.0055(9) C(17) 0.0211(10) 0.0223(10) 0.0261(10) -0.0115(8) 0.0052(8) 0.0005(8) C(18) 0.0244(10) 0.0233(10) 0.0265(10) -0.0123(8) 0.0078(8) 0.0031(8) C(19) 0.0231(10) 0.0209(10) 0.0294(11) -0.0079(8) 0.0042(8) 0.0047(8) C(20) 0.0216(10) 0.0251(11) 0.0307(11) -0.0121(9) 0.0075(8) 0.0012(8) C(21) 0.0287(11) 0.0291(11) 0.0310(11) -0.0144(9) 0.0102(9) 0.0068(9) C(22) 0.0252(11) 0.0231(10) 0.0285(10) -0.0095(8) 0.0037(8) 0.0057(8) C(23) 0.0195(10) 0.0268(11) 0.0254(10) -0.0089(8) 0.0042(8) 0.0032(8) C(24) 0.0230(11) 0.0283(11) 0.0345(12) -0.0107(9) 0.0097(9) 0.0039(9) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F(1) C(18) 1.347(3) yes . . F(2) C(19) 1.350(2) yes . . F(3) C(21) 1.345(3) yes . . F(4) C(22) 1.344(2) yes . . O(1) C(23) 1.248(2) yes . . O(2) C(23) 1.249(3) yes . . O(3) C(24) 1.234(3) yes . . O(4) C(24) 1.248(2) yes . . N(1) C(15) 1.311(3) yes . . N(2) C(15) 1.303(2) yes . . N(3) C(16) 1.307(4) yes . . N(4) C(16) 1.299(2) yes . . C(1) C(2) 1.398(3) yes . . C(1) C(13) 1.399(3) yes . . C(1) C(15) 1.490(3) yes . . C(2) C(3) 1.382(3) yes . . C(3) C(4) 1.383(3) yes . . C(4) C(14) 1.386(3) yes . . C(5) C(6) 1.386(3) yes . . C(5) C(12) 1.388(4) yes . . C(6) C(7) 1.389(4) yes . . C(7) C(8) 1.390(4) yes . . C(8) C(11) 1.399(2) yes . . C(8) C(16) 1.489(3) yes . . C(9) C(11) 1.509(4) yes . . C(9) C(13) 1.514(3) yes . . C(10) C(12) 1.508(3) yes . . C(10) C(14) 1.511(3) yes . . C(11) C(12) 1.408(3) yes . . C(13) C(14) 1.401(3) yes . . C(17) C(18) 1.389(2) yes . . C(17) C(22) 1.383(4) yes . . C(17) C(23) 1.526(3) yes . . C(18) C(19) 1.377(3) yes . . C(19) C(20) 1.372(4) yes . . C(20) C(21) 1.383(3) yes . . C(20) C(24) 1.527(3) yes . . C(21) C(22) 1.385(3) yes . . O(6) H(19) 0.73(4) no . . O(6) H(20) 1.03(3) no . . N(1) H(11) 0.90(2) no . . N(1) H(12) 0.95(4) no . . N(2) H(13) 0.89(3) no . . N(2) H(14) 0.91(4) no . . N(3) H(15) 0.85(2) no . . N(3) H(16) 0.86(4) no . . N(4) H(17) 0.87(4) no . . N(4) H(18) 0.91(4) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.980 no . . C(9) H(8) 0.980 no . . C(10) H(9) 0.980 no . . C(10) H(10) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(13) 120.3(2) yes . . . C(2) C(1) C(15) 116.2(2) yes . . . C(13) C(1) C(15) 123.31(19) yes . . . C(1) C(2) C(3) 120.2(2) yes . . . C(2) C(3) C(4) 119.8(2) yes . . . C(3) C(4) C(14) 120.5(2) yes . . . C(6) C(5) C(12) 121.1(2) yes . . . C(5) C(6) C(7) 119.5(3) yes . . . C(6) C(7) C(8) 120.2(2) yes . . . C(7) C(8) C(11) 120.8(2) yes . . . C(7) C(8) C(16) 117.41(19) yes . . . C(11) C(8) C(16) 121.7(2) yes . . . C(11) C(9) C(13) 111.3(2) yes . . . C(12) C(10) C(14) 110.66(17) yes . . . C(8) C(11) C(9) 123.5(2) yes . . . C(8) C(11) C(12) 118.7(2) yes . . . C(9) C(11) C(12) 117.72(19) yes . . . C(5) C(12) C(10) 122.8(2) yes . . . C(5) C(12) C(11) 119.8(2) yes . . . C(10) C(12) C(11) 117.4(2) yes . . . C(1) C(13) C(9) 124.1(2) yes . . . C(1) C(13) C(14) 118.5(2) yes . . . C(9) C(13) C(14) 117.4(2) yes . . . C(4) C(14) C(10) 121.5(2) yes . . . C(4) C(14) C(13) 120.6(2) yes . . . C(10) C(14) C(13) 117.94(19) yes . . . N(1) C(15) N(2) 120.1(2) yes . . . N(1) C(15) C(1) 122.69(18) yes . . . N(2) C(15) C(1) 117.2(2) yes . . . N(3) C(16) N(4) 121.6(2) yes . . . N(3) C(16) C(8) 121.28(19) yes . . . N(4) C(16) C(8) 117.1(2) yes . . . C(18) C(17) C(22) 115.8(2) yes . . . C(18) C(17) C(23) 121.4(2) yes . . . C(22) C(17) C(23) 122.78(19) yes . . . F(1) C(18) C(17) 121.1(2) yes . . . F(1) C(18) C(19) 117.30(19) yes . . . C(17) C(18) C(19) 121.6(2) yes . . . F(2) C(19) C(18) 118.6(2) yes . . . F(2) C(19) C(20) 119.09(19) yes . . . C(18) C(19) C(20) 122.4(2) yes . . . C(19) C(20) C(21) 116.6(2) yes . . . C(19) C(20) C(24) 120.2(2) yes . . . C(21) C(20) C(24) 123.2(2) yes . . . F(3) C(21) C(20) 119.9(2) yes . . . F(3) C(21) C(22) 118.8(2) yes . . . C(20) C(21) C(22) 121.2(2) yes . . . F(4) C(22) C(17) 119.7(2) yes . . . F(4) C(22) C(21) 118.0(2) yes . . . C(17) C(22) C(21) 122.3(2) yes . . . O(1) C(23) O(2) 126.4(2) yes . . . O(1) C(23) C(17) 117.7(2) yes . . . O(2) C(23) C(17) 115.92(18) yes . . . O(3) C(24) O(4) 126.4(2) yes . . . O(3) C(24) C(20) 117.32(18) yes . . . O(4) C(24) C(20) 116.2(2) yes . . . H(19) O(6) H(20) 111(4) no . . . C(15) N(1) H(11) 121(2) no . . . C(15) N(1) H(12) 117(2) no . . . H(11) N(1) H(12) 122(3) no . . . C(15) N(2) H(13) 118(2) no . . . C(15) N(2) H(14) 117(2) no . . . H(13) N(2) H(14) 124(3) no . . . C(16) N(3) H(15) 120(2) no . . . C(16) N(3) H(16) 118(2) no . . . H(15) N(3) H(16) 123(4) no . . . C(16) N(4) H(17) 120(2) no . . . C(16) N(4) H(18) 118(2) no . . . H(17) N(4) H(18) 120(3) no . . . C(1) C(2) H(1) 119.9 no . . . C(3) C(2) H(1) 119.9 no . . . C(2) C(3) H(2) 120.1 no . . . C(4) C(3) H(2) 120.1 no . . . C(3) C(4) H(3) 119.8 no . . . C(14) C(4) H(3) 119.8 no . . . C(6) C(5) H(4) 119.5 no . . . C(12) C(5) H(4) 119.5 no . . . C(5) C(6) H(5) 120.3 no . . . C(7) C(6) H(5) 120.3 no . . . C(6) C(7) H(6) 119.9 no . . . C(8) C(7) H(6) 119.9 no . . . C(11) C(9) H(7) 109.4 no . . . C(11) C(9) H(8) 109.4 no . . . C(13) C(9) H(7) 109.4 no . . . C(13) C(9) H(8) 109.4 no . . . H(7) C(9) H(8) 108.0 no . . . C(12) C(10) H(9) 109.5 no . . . C(12) C(10) H(10) 109.5 no . . . C(14) C(10) H(9) 109.5 no . . . C(14) C(10) H(10) 109.5 no . . . H(9) C(10) H(10) 108.1 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(13) C(9) -179.3(2) ? . . . . C(2) C(1) C(13) C(14) 2.6(3) ? . . . . C(13) C(1) C(2) C(3) -0.6(4) ? . . . . C(2) C(1) C(15) N(1) 130.8(2) ? . . . . C(2) C(1) C(15) N(2) -48.3(3) ? . . . . C(15) C(1) C(2) C(3) 174.9(2) ? . . . . C(13) C(1) C(15) N(1) -53.8(3) ? . . . . C(13) C(1) C(15) N(2) 127.0(2) ? . . . . C(15) C(1) C(13) C(9) 5.6(4) ? . . . . C(15) C(1) C(13) C(14) -172.6(2) ? . . . . C(1) C(2) C(3) C(4) -2.1(4) ? . . . . C(2) C(3) C(4) C(14) 2.7(4) ? . . . . C(3) C(4) C(14) C(10) -178.5(2) ? . . . . C(3) C(4) C(14) C(13) -0.7(3) ? . . . . C(6) C(5) C(12) C(10) 178.2(2) ? . . . . C(6) C(5) C(12) C(11) 0.6(3) ? . . . . C(12) C(5) C(6) C(7) 1.5(3) ? . . . . C(5) C(6) C(7) C(8) -1.5(3) ? . . . . C(6) C(7) C(8) C(11) -0.7(3) ? . . . . C(6) C(7) C(8) C(16) -176.4(2) ? . . . . C(7) C(8) C(11) C(9) -172.9(2) ? . . . . C(7) C(8) C(11) C(12) 2.8(3) ? . . . . C(7) C(8) C(16) N(3) -126.3(2) ? . . . . C(7) C(8) C(16) N(4) 52.5(2) ? . . . . C(11) C(8) C(16) N(3) 58.0(3) ? . . . . C(11) C(8) C(16) N(4) -123.2(2) ? . . . . C(16) C(8) C(11) C(9) 2.7(3) ? . . . . C(16) C(8) C(11) C(12) 178.33(19) ? . . . . C(11) C(9) C(13) C(1) -137.0(2) ? . . . . C(11) C(9) C(13) C(14) 41.2(2) ? . . . . C(13) C(9) C(11) C(8) 138.1(2) ? . . . . C(13) C(9) C(11) C(12) -37.6(2) ? . . . . C(12) C(10) C(14) C(4) 138.3(2) ? . . . . C(12) C(10) C(14) C(13) -39.7(3) ? . . . . C(14) C(10) C(12) C(5) -134.4(2) ? . . . . C(14) C(10) C(12) C(11) 43.2(3) ? . . . . C(8) C(11) C(12) C(5) -2.7(3) ? . . . . C(8) C(11) C(12) C(10) 179.59(19) ? . . . . C(9) C(11) C(12) C(5) 173.2(2) ? . . . . C(9) C(11) C(12) C(10) -4.5(2) ? . . . . C(1) C(13) C(14) C(4) -2.0(3) ? . . . . C(1) C(13) C(14) C(10) 176.0(2) ? . . . . C(9) C(13) C(14) C(4) 179.7(2) ? . . . . C(9) C(13) C(14) C(10) -2.3(3) ? . . . . C(18) C(17) C(22) F(4) 178.00(18) ? . . . . C(18) C(17) C(22) C(21) -0.2(3) ? . . . . C(22) C(17) C(18) F(1) -178.50(18) ? . . . . C(22) C(17) C(18) C(19) 2.4(3) ? . . . . C(18) C(17) C(23) O(1) 132.0(2) ? . . . . C(18) C(17) C(23) O(2) -46.9(2) ? . . . . C(23) C(17) C(18) F(1) 2.2(3) ? . . . . C(23) C(17) C(18) C(19) -176.84(19) ? . . . . C(22) C(17) C(23) O(1) -47.2(2) ? . . . . C(22) C(17) C(23) O(2) 133.8(2) ? . . . . C(23) C(17) C(22) F(4) -2.7(3) ? . . . . C(23) C(17) C(22) C(21) 179.1(2) ? . . . . F(1) C(18) C(19) F(2) -2.0(2) ? . . . . F(1) C(18) C(19) C(20) 177.18(19) ? . . . . C(17) C(18) C(19) F(2) 177.10(19) ? . . . . C(17) C(18) C(19) C(20) -3.7(3) ? . . . . F(2) C(19) C(20) C(21) -178.38(19) ? . . . . F(2) C(19) C(20) C(24) 3.8(3) ? . . . . C(18) C(19) C(20) C(21) 2.4(3) ? . . . . C(18) C(19) C(20) C(24) -175.4(2) ? . . . . C(19) C(20) C(21) F(3) -178.8(2) ? . . . . C(19) C(20) C(21) C(22) -0.2(3) ? . . . . C(19) C(20) C(24) O(3) -106.8(3) ? . . . . C(19) C(20) C(24) O(4) 71.5(3) ? . . . . C(21) C(20) C(24) O(3) 75.6(3) ? . . . . C(21) C(20) C(24) O(4) -106.2(3) ? . . . . C(24) C(20) C(21) F(3) -1.1(3) ? . . . . C(24) C(20) C(21) C(22) 177.6(2) ? . . . . F(3) C(21) C(22) F(4) -0.5(3) ? . . . . F(3) C(21) C(22) C(17) 177.7(2) ? . . . . C(20) C(21) C(22) F(4) -179.2(2) ? . . . . C(20) C(21) C(22) C(17) -1.0(3) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F(1) F(1) 2.7072(17) ? . 2_867 F(1) O(1) 3.329(2) ? . 2_867 F(1) C(2) 3.430(2) ? . 2_766 F(1) C(3) 3.565(2) ? . 2_766 F(1) C(5) 3.492(3) ? . 2_767 F(1) C(6) 3.230(4) ? . 2_767 F(1) C(17) 3.165(2) ? . 2_867 F(1) C(18) 2.953(2) ? . 2_867 F(1) C(23) 3.158(2) ? . 2_867 F(2) O(1) 3.242(2) ? . 2_867 F(2) O(2) 3.554(2) ? . 2_867 F(2) O(6) 3.056(3) ? . 2_867 F(2) N(3) 3.372(2) ? . 2_867 F(2) N(4) 3.539(2) ? . 2_867 F(2) C(23) 3.491(2) ? . 2_867 F(3) F(4) 3.190(2) ? . 2_866 F(3) C(13) 3.527(3) ? . 1_655 F(3) C(22) 3.399(2) ? . 2_866 F(4) F(3) 3.190(2) ? . 2_866 F(4) O(7) 3.108(2) ? . . F(4) C(4) 3.100(3) ? . 1_655 F(4) C(10) 3.364(3) ? . 1_655 F(4) C(12) 3.533(2) ? . 1_655 F(4) C(14) 3.242(3) ? . 1_655 F(4) C(21) 3.197(2) ? . 2_866 F(4) C(22) 3.524(2) ? . 2_866 O(1) F(1) 3.329(2) ? . 2_867 O(1) F(2) 3.242(2) ? . 2_867 O(1) O(6) 2.881(2) ? . . O(1) O(7) 2.806(2) ? . . O(1) N(3) 3.192(3) ? . . O(1) N(4) 3.578(3) ? . . O(2) F(2) 3.554(2) ? . 2_867 O(2) N(2) 2.831(3) ? . 2_766 O(2) N(4) 2.781(2) ? . . O(3) N(2) 2.794(3) ? . 2_866 O(3) N(4) 2.783(3) ? . 1_655 O(4) O(7) 2.825(2) ? . 2_866 O(4) N(1) 2.913(2) ? . 2_866 O(5) O(6) 2.890(3) ? . 1_644 O(5) O(7) 2.727(2) ? . 2_866 O(5) N(1) 3.019(2) ? . 2_866 O(5) C(3) 3.307(2) ? . 1_745 O(5) C(4) 3.598(2) ? . 1_745 O(6) F(2) 3.056(3) ? . 2_867 O(6) O(1) 2.881(2) ? . . O(6) O(5) 2.890(3) ? . 1_466 O(6) N(3) 3.218(3) ? . . O(6) N(3) 2.884(3) ? . 2_777 O(6) C(9) 3.290(3) ? . 2_777 O(7) F(4) 3.108(2) ? . . O(7) O(1) 2.806(2) ? . . O(7) O(4) 2.825(2) ? . 2_866 O(7) O(5) 2.727(2) ? . 2_866 O(7) N(1) 3.560(3) ? . . O(7) C(4) 3.502(4) ? . 1_655 N(1) O(4) 2.913(2) ? . 2_866 N(1) O(5) 3.019(2) ? . 2_866 N(1) O(7) 3.560(3) ? . . N(1) C(4) 3.317(2) ? . 2_676 N(2) O(2) 2.831(3) ? . 2_766 N(2) O(3) 2.794(3) ? . 2_866 N(2) N(4) 3.527(2) ? . 2_766 N(2) C(24) 3.538(3) ? . 2_866 N(3) F(2) 3.372(2) ? . 2_867 N(3) O(1) 3.192(3) ? . . N(3) O(6) 3.218(3) ? . . N(3) O(6) 2.884(3) ? . 2_777 N(4) F(2) 3.539(2) ? . 2_867 N(4) O(1) 3.578(3) ? . . N(4) O(2) 2.781(2) ? . . N(4) O(3) 2.783(3) ? . 1_455 N(4) N(2) 3.527(2) ? . 2_766 N(4) C(23) 3.532(3) ? . . C(2) F(1) 3.430(2) ? . 2_766 C(2) C(13) 3.596(3) ? . 2_676 C(3) F(1) 3.565(2) ? . 2_766 C(3) O(5) 3.307(2) ? . 1_365 C(3) C(18) 3.480(3) ? . 2_766 C(3) C(19) 3.501(3) ? . 2_766 C(4) F(4) 3.100(3) ? . 1_455 C(4) O(5) 3.598(2) ? . 1_365 C(4) O(7) 3.502(4) ? . 1_455 C(4) N(1) 3.317(2) ? . 2_676 C(5) F(1) 3.492(3) ? . 2_767 C(5) C(22) 3.360(3) ? . 1_455 C(6) F(1) 3.230(4) ? . 2_767 C(9) O(6) 3.290(3) ? . 2_777 C(10) F(4) 3.364(3) ? . 1_455 C(12) F(4) 3.533(2) ? . 1_455 C(13) F(3) 3.527(3) ? . 1_455 C(13) C(2) 3.596(3) ? . 2_676 C(14) F(4) 3.242(3) ? . 1_455 C(17) F(1) 3.165(2) ? . 2_867 C(18) F(1) 2.953(2) ? . 2_867 C(18) C(3) 3.480(3) ? . 2_766 C(19) C(3) 3.501(3) ? . 2_766 C(21) F(4) 3.197(2) ? . 2_866 C(22) F(3) 3.399(2) ? . 2_866 C(22) F(4) 3.524(2) ? . 2_866 C(22) C(5) 3.360(3) ? . 1_655 C(23) F(1) 3.158(2) ? . 2_867 C(23) F(2) 3.491(2) ? . 2_867 C(23) N(4) 3.532(3) ? . . C(24) N(2) 3.538(3) ? . 2_866 F(1) H(1) 2.875 ? . 2_766 F(1) H(2) 3.159 ? . 2_766 F(1) H(4) 3.030 ? . 2_767 F(1) H(5) 2.501 ? . 2_767 F(1) H(20) 3.28(4) ? . 2_867 F(2) H(2) 2.820 ? . 2_766 F(2) H(16) 3.03(3) ? . 2_867 F(2) H(17) 3.25(3) ? . 2_867 F(2) H(19) 2.62(3) ? . 2_867 F(2) H(20) 2.77(6) ? . 2_867 F(3) H(14) 3.56(5) ? . 1_655 F(4) H(3) 3.002 ? . 1_655 F(4) H(4) 3.469 ? . 1_655 F(4) H(10) 2.957 ? . 1_655 O(1) H(4) 2.970 ? . 1_655 O(1) H(10) 3.531 ? . 1_655 O(1) H(16) 2.35(4) ? . . O(1) H(17) 2.85(5) ? . . O(1) H(19) 3.24(2) ? . . O(1) H(20) 1.90(4) ? . . O(2) H(1) 3.344 ? . 2_766 O(2) H(5) 2.794 ? . 2_767 O(2) H(13) 3.17(4) ? . 2_766 O(2) H(14) 2.00(4) ? . 2_766 O(2) H(16) 3.32(3) ? . . O(2) H(17) 1.92(4) ? . . O(2) H(18) 3.22(4) ? . . O(3) H(6) 3.557 ? . 1_655 O(3) H(6) 2.843 ? . 2_867 O(3) H(12) 2.95(2) ? . 2_866 O(3) H(13) 1.91(3) ? . 2_866 O(3) H(14) 3.36(4) ? . 2_866 O(3) H(17) 3.19(4) ? . 1_655 O(3) H(18) 1.90(4) ? . 1_655 O(4) H(3) 3.489 ? . 2_766 O(4) H(11) 3.47(2) ? . 2_866 O(4) H(12) 1.97(4) ? . 2_866 O(4) H(13) 2.92(4) ? . 2_866 O(5) H(2) 2.569 ? . 1_745 O(5) H(3) 3.166 ? . 1_745 O(5) H(7) 3.489 ? . 2_866 O(5) H(8) 3.409 ? . 2_866 O(5) H(11) 2.35(3) ? . 2_866 O(5) H(12) 3.17(3) ? . 2_866 O(5) H(19) 2.19(3) ? . 1_644 O(5) H(20) 3.57(5) ? . 1_644 O(6) H(2) 3.317 ? . 1_656 O(6) H(4) 3.040 ? . 1_655 O(6) H(7) 3.351 ? . 2_777 O(6) H(8) 2.537 ? . 2_777 O(6) H(15) 3.23(3) ? . . O(6) H(15) 2.08(3) ? . 2_777 O(6) H(16) 2.68(4) ? . . O(6) H(16) 3.32(3) ? . 2_777 O(7) H(3) 2.642 ? . 1_655 O(7) H(10) 2.964 ? . 1_655 O(7) H(11) 3.58(3) ? . . O(7) H(12) 3.04(3) ? . . O(7) H(16) 3.29(5) ? . . O(7) H(20) 3.39(4) ? . . N(1) H(3) 3.061 ? . 2_676 N(2) H(5) 3.115 ? . 1_554 N(2) H(6) 3.229 ? . 1_554 N(2) H(17) 3.17(3) ? . 2_766 N(2) H(18) 3.19(3) ? . 2_766 N(3) H(19) 3.21(3) ? . . N(3) H(19) 3.08(3) ? . 2_777 N(3) H(20) 3.14(5) ? . . N(4) H(6) 3.327 ? . 2_767 N(4) H(13) 3.09(2) ? . 2_766 N(4) H(14) 3.33(3) ? . 2_766 C(2) H(5) 3.271 ? . 1_554 C(2) H(8) 3.383 ? . 2_676 C(3) H(8) 3.176 ? . 2_676 C(3) H(11) 2.85(2) ? . 2_676 C(4) H(11) 2.69(2) ? . 2_676 C(5) H(1) 3.456 ? . 1_556 C(5) H(9) 2.920 ? . 2_677 C(5) H(20) 3.39(5) ? . 1_455 C(6) H(1) 2.943 ? . 1_556 C(6) H(9) 3.140 ? . 2_677 C(6) H(14) 3.50(4) ? . 1_556 C(7) H(9) 3.542 ? . 2_677 C(7) H(13) 3.57(3) ? . 1_556 C(9) H(19) 3.29(3) ? . 2_777 C(12) H(9) 3.179 ? . 2_677 C(17) H(4) 3.360 ? . 1_655 C(18) H(1) 3.423 ? . 2_766 C(18) H(2) 3.123 ? . 2_766 C(19) H(2) 2.923 ? . 2_766 C(22) H(4) 3.329 ? . 1_655 C(23) H(4) 3.557 ? . 1_655 C(23) H(14) 3.10(4) ? . 2_766 C(23) H(16) 3.16(3) ? . . C(23) H(17) 2.67(4) ? . . C(23) H(20) 2.99(4) ? . . C(24) H(12) 2.74(3) ? . 2_866 C(24) H(13) 2.69(4) ? . 2_866 C(24) H(18) 3.08(4) ? . 1_655 H(1) F(1) 2.875 ? . 2_766 H(1) O(2) 3.344 ? . 2_766 H(1) C(5) 3.456 ? . 1_554 H(1) C(6) 2.943 ? . 1_554 H(1) C(18) 3.423 ? . 2_766 H(1) H(4) 3.308 ? . 1_554 H(1) H(5) 2.360 ? . 1_554 H(1) H(8) 3.248 ? . 2_676 H(1) H(9) 3.162 ? . 2_676 H(2) F(1) 3.159 ? . 2_766 H(2) F(2) 2.820 ? . 2_766 H(2) O(5) 2.569 ? . 1_365 H(2) O(6) 3.317 ? . 1_454 H(2) C(18) 3.123 ? . 2_766 H(2) C(19) 2.923 ? . 2_766 H(2) H(8) 2.852 ? . 2_676 H(2) H(11) 2.730 ? . 2_676 H(2) H(19) 2.791 ? . 1_454 H(2) H(20) 3.549 ? . 1_454 H(3) F(4) 3.002 ? . 1_455 H(3) O(4) 3.489 ? . 2_766 H(3) O(5) 3.166 ? . 1_365 H(3) O(7) 2.642 ? . 1_455 H(3) N(1) 3.061 ? . 2_676 H(3) H(11) 2.477 ? . 2_676 H(3) H(12) 3.435 ? . 2_676 H(4) F(1) 3.030 ? . 2_767 H(4) F(4) 3.469 ? . 1_455 H(4) O(1) 2.970 ? . 1_455 H(4) O(6) 3.040 ? . 1_455 H(4) C(17) 3.360 ? . 1_455 H(4) C(22) 3.329 ? . 1_455 H(4) C(23) 3.557 ? . 1_455 H(4) H(1) 3.308 ? . 1_556 H(4) H(8) 3.416 ? . 2_677 H(4) H(9) 3.171 ? . 2_677 H(4) H(19) 3.451 ? . 1_455 H(4) H(20) 2.452 ? . 1_455 H(5) F(1) 2.501 ? . 2_767 H(5) O(2) 2.794 ? . 2_767 H(5) N(2) 3.115 ? . 1_556 H(5) C(2) 3.271 ? . 1_556 H(5) H(1) 2.360 ? . 1_556 H(5) H(9) 3.525 ? . 2_677 H(5) H(13) 3.420 ? . 1_556 H(5) H(14) 2.774 ? . 1_556 H(5) H(17) 3.571 ? . 2_767 H(6) O(3) 3.557 ? . 1_455 H(6) O(3) 2.843 ? . 2_867 H(6) N(2) 3.229 ? . 1_556 H(6) N(4) 3.327 ? . 2_767 H(6) H(13) 2.898 ? . 1_556 H(6) H(14) 3.408 ? . 1_556 H(6) H(17) 3.379 ? . 2_767 H(6) H(18) 2.870 ? . 2_767 H(7) O(5) 3.489 ? . 2_866 H(7) O(6) 3.351 ? . 2_777 H(7) H(19) 3.247 ? . 2_777 H(8) O(5) 3.409 ? . 2_866 H(8) O(6) 2.537 ? . 2_777 H(8) C(2) 3.383 ? . 2_676 H(8) C(3) 3.176 ? . 2_676 H(8) H(1) 3.248 ? . 2_676 H(8) H(2) 2.852 ? . 2_676 H(8) H(4) 3.416 ? . 2_677 H(8) H(19) 2.513 ? . 2_777 H(8) H(20) 3.177 ? . 2_777 H(9) C(5) 2.920 ? . 2_677 H(9) C(6) 3.140 ? . 2_677 H(9) C(7) 3.542 ? . 2_677 H(9) C(12) 3.179 ? . 2_677 H(9) H(1) 3.162 ? . 2_676 H(9) H(4) 3.171 ? . 2_677 H(9) H(5) 3.525 ? . 2_677 H(10) F(4) 2.957 ? . 1_455 H(10) O(1) 3.531 ? . 1_455 H(10) O(7) 2.964 ? . 1_455 H(10) H(20) 3.293 ? . 1_455 H(11) O(4) 3.47(2) ? . 2_866 H(11) O(5) 2.35(3) ? . 2_866 H(11) O(7) 3.58(3) ? . . H(11) C(3) 2.85(2) ? . 2_676 H(11) C(4) 2.69(2) ? . 2_676 H(11) H(2) 2.730 ? . 2_676 H(11) H(3) 2.477 ? . 2_676 H(11) H(19) 3.56(4) ? . 2_777 H(12) O(3) 2.95(2) ? . 2_866 H(12) O(4) 1.97(4) ? . 2_866 H(12) O(5) 3.17(3) ? . 2_866 H(12) O(7) 3.04(3) ? . . H(12) C(24) 2.74(3) ? . 2_866 H(12) H(3) 3.435 ? . 2_676 H(13) O(2) 3.17(4) ? . 2_766 H(13) O(3) 1.91(3) ? . 2_866 H(13) O(4) 2.92(4) ? . 2_866 H(13) N(4) 3.09(2) ? . 2_766 H(13) C(7) 3.57(3) ? . 1_554 H(13) C(24) 2.69(4) ? . 2_866 H(13) H(5) 3.420 ? . 1_554 H(13) H(6) 2.898 ? . 1_554 H(13) H(17) 2.95(4) ? . 2_766 H(13) H(18) 2.57(4) ? . 2_766 H(14) F(3) 3.56(5) ? . 1_455 H(14) O(2) 2.00(4) ? . 2_766 H(14) O(3) 3.36(4) ? . 2_866 H(14) N(4) 3.33(3) ? . 2_766 H(14) C(6) 3.50(4) ? . 1_554 H(14) C(23) 3.10(4) ? . 2_766 H(14) H(5) 2.774 ? . 1_554 H(14) H(6) 3.408 ? . 1_554 H(14) H(17) 2.78(4) ? . 2_766 H(14) H(18) 3.23(4) ? . 2_766 H(15) O(6) 3.23(3) ? . . H(15) O(6) 2.08(3) ? . 2_777 H(15) H(19) 3.20(4) ? . . H(15) H(19) 2.37(5) ? . 2_777 H(15) H(20) 3.41(6) ? . . H(15) H(20) 2.96(5) ? . 2_777 H(16) F(2) 3.03(3) ? . 2_867 H(16) O(1) 2.35(4) ? . . H(16) O(2) 3.32(3) ? . . H(16) O(6) 2.68(4) ? . . H(16) O(6) 3.32(3) ? . 2_777 H(16) O(7) 3.29(5) ? . . H(16) C(23) 3.16(3) ? . . H(16) H(19) 2.78(5) ? . . H(16) H(19) 3.40(4) ? . 2_777 H(16) H(20) 2.41(7) ? . . H(17) F(2) 3.25(3) ? . 2_867 H(17) O(1) 2.85(5) ? . . H(17) O(2) 1.92(4) ? . . H(17) O(3) 3.19(4) ? . 1_455 H(17) N(2) 3.17(3) ? . 2_766 H(17) C(23) 2.67(4) ? . . H(17) H(5) 3.571 ? . 2_767 H(17) H(6) 3.379 ? . 2_767 H(17) H(13) 2.95(4) ? . 2_766 H(17) H(14) 2.78(4) ? . 2_766 H(19) F(2) 2.62(3) ? . 2_867 H(19) O(1) 3.24(2) ? . . H(19) O(5) 2.19(3) ? . 1_466 H(19) N(3) 3.21(3) ? . . H(19) N(3) 3.08(3) ? . 2_777 H(19) C(9) 3.29(3) ? . 2_777 H(19) H(2) 2.791 ? . 1_656 H(19) H(4) 3.451 ? . 1_655 H(19) H(7) 3.247 ? . 2_777 H(19) H(8) 2.513 ? . 2_777 H(19) H(11) 3.56(4) ? . 2_777 H(19) H(15) 3.20(4) ? . . H(19) H(15) 2.37(5) ? . 2_777 H(19) H(16) 2.78(5) ? . . H(19) H(16) 3.40(4) ? . 2_777 H(20) F(1) 3.28(4) ? . 2_867 H(20) F(2) 2.77(6) ? . 2_867 H(20) O(1) 1.90(4) ? . . H(20) O(5) 3.57(5) ? . 1_466 H(20) O(7) 3.39(4) ? . . H(20) N(3) 3.14(5) ? . . H(20) C(5) 3.39(5) ? . 1_655 H(20) C(23) 2.99(4) ? . . H(20) H(2) 3.549 ? . 1_656 H(20) H(4) 2.452 ? . 1_655 H(20) H(8) 3.177 ? . 2_777 H(20) H(10) 3.293 ? . 1_655 H(20) H(15) 3.41(6) ? . . H(20) H(15) 2.96(5) ? . 2_777 H(20) H(16) 2.41(7) ? . . H(18) O(2) 3.22(4) ? . . H(18) O(3) 1.90(4) ? . 1_455 H(18) N(2) 3.19(3) ? . 2_766 H(18) C(24) 3.08(4) ? . 1_455 H(18) H(6) 2.870 ? . 2_767 H(18) H(13) 2.57(4) ? . 2_766 H(18) H(14) 3.23(4) ? . 2_766 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__kusu075 _database_code_depnum_ccdc_archive 'CCDC 920480' #TrackingRef '16982_web_deposit_cif_file_0_TakahiroKusukawa_1358506421.1b2_2a2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H28 N4 O9 ' _chemical_formula_moiety 'C22 H28 N4 O9 ' _chemical_formula_weight 492.48 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.197(5) _cell_length_b 11.525(6) _cell_length_c 10.753(5) _cell_angle_alpha 116.02(3) _cell_angle_beta 90.97(3) _cell_angle_gamma 73.52(4) _cell_volume 1186.3(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 25.1 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520.00 _exptl_absorpt_coefficient_mu 0.917 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.713 _exptl_absorpt_correction_T_max 0.832 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 5774 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_theta_max 67.08 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.08 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -8.71 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4217 _reflns_number_gt 2027 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0913 _refine_ls_wR_factor_ref 0.3154 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4217 _refine_ls_number_parameters 324 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.79 _refine_diff_density_min -0.47 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 0.5419(3) 0.7879(3) 0.2603(3) 0.0430(9) Uani 1.00 1 d . . . O(2) O 0.3724(3) 0.9605(3) 0.3834(4) 0.0492(10) Uani 1.00 1 d . . . O(3) O 0.6990(3) 1.1816(3) -0.0166(4) 0.0525(10) Uani 1.00 1 d . . . O(4) O 0.5489(4) 1.3617(3) 0.1317(4) 0.0520(10) Uani 1.00 1 d . . . O(5) O 0.2374(3) 1.1882(4) 0.6181(4) 0.0538(10) Uiso 1.00 1 d . . . O(6) O 0.1714(4) 1.0513(5) 0.2453(5) 0.0768(14) Uiso 1.00 1 d . . . O(7) O 0.9556(4) 1.0644(5) 0.3605(5) 0.0705(13) Uiso 1.00 1 d . . . O(8) O 0.088(2) 0.920(2) -0.099(2) 0.449(14) Uiso 1.00 1 d . . . O(9) O 0.9957(4) 1.1904(4) 0.6451(4) 0.0586(11) Uiso 1.00 1 d . . . N(1) N 0.3358(4) 0.4904(5) -0.0568(4) 0.0451(12) Uani 1.00 1 d . . . N(2) N 0.2143(4) 0.6780(4) 0.1322(4) 0.0429(11) Uani 1.00 1 d . . . N(3) N 0.4297(4) 0.6286(5) 0.3304(5) 0.0424(11) Uani 1.00 1 d . . . N(4) N 0.2951(4) 0.8174(4) 0.5065(4) 0.0435(11) Uani 1.00 1 d . . . C(1) C 0.1918(4) 0.4620(4) 0.0834(5) 0.0351(11) Uani 1.00 1 d . . . C(2) C 0.1372(5) 0.3715(5) -0.0203(5) 0.0432(13) Uani 1.00 1 d . . . C(3) C 0.0818(5) 0.2910(5) 0.0076(6) 0.0492(13) Uani 1.00 1 d . . . C(4) C 0.0760(5) 0.2918(5) 0.1374(6) 0.0500(14) Uani 1.00 1 d . . . C(5) C 0.1591(5) 0.4294(6) 0.5090(6) 0.0492(14) Uani 1.00 1 d . . . C(6) C 0.2158(5) 0.5166(6) 0.6117(6) 0.0548(15) Uani 1.00 1 d . . . C(7) C 0.2697(5) 0.5984(6) 0.5877(6) 0.0480(14) Uani 1.00 1 d . . . C(8) C 0.2750(4) 0.5989(5) 0.4564(5) 0.0380(12) Uani 1.00 1 d . . . C(9) C 0.2198(4) 0.5159(5) 0.3575(5) 0.0356(11) Uani 1.00 1 d . . . C(10) C 0.1620(4) 0.4325(5) 0.3835(5) 0.0414(12) Uani 1.00 1 d . . . C(11) C 0.1296(4) 0.3787(5) 0.2384(5) 0.0401(12) Uani 1.00 1 d . . . C(12) C 0.1865(4) 0.4621(4) 0.2108(5) 0.0359(11) Uani 1.00 1 d . . . C(13) C 0.2499(4) 0.5467(4) 0.0518(4) 0.0332(10) Uani 1.00 1 d . . . C(14) C 0.3366(4) 0.6853(5) 0.4294(5) 0.0342(11) Uani 1.00 1 d . . . C(15) C 0.5088(4) 0.9933(4) 0.2458(5) 0.0377(12) Uani 1.00 1 d . . . C(16) C 0.6029(5) 0.9365(5) 0.1336(5) 0.0422(13) Uani 1.00 1 d . . . C(17) C 0.6355(5) 1.0135(5) 0.0807(5) 0.0432(13) Uani 1.00 1 d . . . C(18) C 0.5750(4) 1.1533(4) 0.1383(5) 0.0349(11) Uani 1.00 1 d . . . C(19) C 0.4831(5) 1.2116(5) 0.2503(5) 0.0431(13) Uani 1.00 1 d . . . C(20) C 0.4485(5) 1.1336(5) 0.3029(5) 0.0451(13) Uani 1.00 1 d . . . C(21) C 0.4718(4) 0.9083(5) 0.3002(5) 0.0385(12) Uani 1.00 1 d . . . C(22) C 0.6089(5) 1.2383(5) 0.0804(5) 0.0396(12) Uani 1.00 1 d . . . H(1) H 0.1389 0.3662 -0.1100 0.052 Uiso 1.00 1 c R . . H(2) H 0.0465 0.2332 -0.0641 0.059 Uiso 1.00 1 c R . . H(3) H 0.0381 0.2366 0.1550 0.060 Uiso 1.00 1 c R . . H(4) H 0.1220 0.3731 0.5258 0.059 Uiso 1.00 1 c R . . H(5) H 0.2163 0.5184 0.6999 0.066 Uiso 1.00 1 c R . . H(6) H 0.3043 0.6561 0.6604 0.058 Uiso 1.00 1 c R . . H(7) H 0.6451 0.8428 0.0934 0.051 Uiso 1.00 1 c R . . H(8) H 0.6992 0.9720 0.0050 0.052 Uiso 1.00 1 c R . . H(9) H 0.4431 1.3057 0.2917 0.052 Uiso 1.00 1 c R . . H(10) H 0.3839 1.1752 0.3777 0.054 Uiso 1.00 1 c R . . H(11) H 0.363(4) 0.417(5) -0.095(5) 0.026(14) Uiso 1.00 1 c . . . H(12) H 0.380(5) 0.551(6) -0.078(6) 0.061(18) Uiso 1.00 1 c . . . H(13) H 0.245(5) 0.727(5) 0.090(6) 0.050(16) Uiso 1.00 1 c . . . H(14) H 0.151(6) 0.710(7) 0.195(7) 0.07(2) Uiso 1.00 1 c . . . H(15) H 0.453(6) 0.533(7) 0.277(6) 0.059(18) Uiso 1.00 1 c . . . H(16) H 0.459(5) 0.676(5) 0.317(5) 0.031(14) Uiso 1.00 1 c . . . H(17) H 0.329(6) 0.868(6) 0.486(6) 0.058(19) Uiso 1.00 1 c . . . H(18) H 0.225(5) 0.859(5) 0.568(5) 0.037(14) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.048(2) 0.0267(18) 0.050(2) -0.0064(16) 0.0099(16) 0.0156(16) O(2) 0.051(2) 0.032(2) 0.055(2) -0.0047(17) 0.0233(18) 0.0158(17) O(3) 0.062(2) 0.034(2) 0.055(2) -0.0069(18) 0.020(2) 0.0178(17) O(4) 0.071(2) 0.0257(19) 0.052(2) -0.0068(18) 0.017(2) 0.0158(17) N(1) 0.055(3) 0.028(2) 0.040(2) -0.004(2) 0.017(2) 0.010(2) N(2) 0.053(2) 0.032(2) 0.040(2) -0.005(2) 0.013(2) 0.016(2) N(3) 0.043(2) 0.031(2) 0.048(2) -0.007(2) 0.013(2) 0.015(2) N(4) 0.050(3) 0.032(2) 0.040(2) -0.010(2) 0.010(2) 0.009(2) C(1) 0.033(2) 0.029(2) 0.037(2) -0.007(2) 0.004(2) 0.011(2) C(2) 0.044(3) 0.034(2) 0.039(2) -0.006(2) -0.001(2) 0.009(2) C(3) 0.046(3) 0.039(3) 0.061(3) -0.019(2) -0.009(2) 0.017(2) C(4) 0.046(3) 0.044(3) 0.063(3) -0.017(2) 0.004(2) 0.024(2) C(5) 0.045(3) 0.050(3) 0.065(3) -0.009(2) 0.006(2) 0.040(3) C(6) 0.056(3) 0.072(4) 0.048(3) -0.022(3) -0.004(2) 0.036(3) C(7) 0.053(3) 0.051(3) 0.043(3) -0.016(2) -0.001(2) 0.023(2) C(8) 0.038(2) 0.038(2) 0.036(2) -0.005(2) 0.003(2) 0.019(2) C(9) 0.038(2) 0.037(2) 0.036(2) -0.012(2) 0.008(2) 0.019(2) C(10) 0.034(2) 0.041(3) 0.051(3) -0.005(2) 0.006(2) 0.026(2) C(11) 0.038(2) 0.031(2) 0.049(3) -0.005(2) 0.004(2) 0.018(2) C(12) 0.036(2) 0.031(2) 0.037(2) -0.009(2) 0.002(2) 0.013(2) C(13) 0.036(2) 0.028(2) 0.030(2) -0.007(2) 0.002(2) 0.011(2) C(14) 0.032(2) 0.031(2) 0.034(2) -0.005(2) -0.003(2) 0.013(2) C(15) 0.040(2) 0.028(2) 0.039(2) -0.009(2) 0.004(2) 0.011(2) C(16) 0.044(3) 0.026(2) 0.050(3) -0.004(2) 0.011(2) 0.014(2) C(17) 0.051(3) 0.034(2) 0.039(2) -0.007(2) 0.010(2) 0.015(2) C(18) 0.036(2) 0.030(2) 0.035(2) -0.008(2) 0.000(2) 0.012(2) C(19) 0.051(3) 0.023(2) 0.044(3) -0.006(2) 0.009(2) 0.009(2) C(20) 0.054(3) 0.030(2) 0.046(3) -0.009(2) 0.014(2) 0.014(2) C(21) 0.041(2) 0.033(2) 0.038(2) -0.011(2) 0.001(2) 0.013(2) C(22) 0.047(3) 0.032(2) 0.036(2) -0.010(2) -0.002(2) 0.013(2) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(21) 1.263(5) yes . . O(2) C(21) 1.258(6) yes . . O(3) C(22) 1.264(6) yes . . O(4) C(22) 1.249(5) yes . . N(1) C(13) 1.315(6) yes . . N(2) C(13) 1.311(6) yes . . N(3) C(14) 1.299(6) yes . . N(4) C(14) 1.313(6) yes . . C(1) C(2) 1.422(7) yes . . C(1) C(12) 1.371(8) yes . . C(1) C(13) 1.466(9) yes . . C(2) C(3) 1.383(10) yes . . C(3) C(4) 1.394(10) yes . . C(4) C(11) 1.381(8) yes . . C(5) C(6) 1.413(8) yes . . C(5) C(10) 1.368(10) yes . . C(6) C(7) 1.364(12) yes . . C(7) C(8) 1.417(9) yes . . C(8) C(9) 1.359(7) yes . . C(8) C(14) 1.484(9) yes . . C(9) C(10) 1.420(10) yes . . C(9) C(12) 1.505(7) yes . . C(10) C(11) 1.486(7) yes . . C(11) C(12) 1.422(9) yes . . C(15) C(16) 1.398(7) yes . . C(15) C(20) 1.403(6) yes . . C(15) C(21) 1.489(9) yes . . C(16) C(17) 1.371(10) yes . . C(17) C(18) 1.399(6) yes . . C(18) C(19) 1.379(7) yes . . C(18) C(22) 1.498(9) yes . . C(19) C(20) 1.389(10) yes . . N(1) H(11) 0.73(5) no . . N(1) H(12) 1.06(8) no . . N(2) H(13) 0.99(8) no . . N(2) H(14) 0.86(7) no . . N(3) H(15) 0.94(6) no . . N(3) H(16) 0.78(7) no . . N(4) H(17) 0.88(9) no . . N(4) H(18) 0.90(5) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(16) H(7) 0.940 no . . C(17) H(8) 0.940 no . . C(19) H(9) 0.940 no . . C(20) H(10) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(12) 115.4(6) yes . . . C(2) C(1) C(13) 120.8(5) yes . . . C(12) C(1) C(13) 123.8(4) yes . . . C(1) C(2) C(3) 121.6(6) yes . . . C(2) C(3) C(4) 122.9(5) yes . . . C(3) C(4) C(11) 115.8(6) yes . . . C(6) C(5) C(10) 115.3(7) yes . . . C(5) C(6) C(7) 122.5(6) yes . . . C(6) C(7) C(8) 121.9(5) yes . . . C(7) C(8) C(9) 115.8(6) yes . . . C(7) C(8) C(14) 121.8(4) yes . . . C(9) C(8) C(14) 122.4(5) yes . . . C(8) C(9) C(10) 122.1(5) yes . . . C(8) C(9) C(12) 148.1(6) yes . . . C(10) C(9) C(12) 89.8(4) yes . . . C(5) C(10) C(9) 122.3(5) yes . . . C(5) C(10) C(11) 147.4(6) yes . . . C(9) C(10) C(11) 90.3(5) yes . . . C(4) C(11) C(10) 147.9(7) yes . . . C(4) C(11) C(12) 121.7(6) yes . . . C(10) C(11) C(12) 90.5(4) yes . . . C(1) C(12) C(9) 147.9(5) yes . . . C(1) C(12) C(11) 122.6(4) yes . . . C(9) C(12) C(11) 89.4(4) yes . . . N(1) C(13) N(2) 121.0(6) yes . . . N(1) C(13) C(1) 119.8(4) yes . . . N(2) C(13) C(1) 119.2(4) yes . . . N(3) C(14) N(4) 121.9(6) yes . . . N(3) C(14) C(8) 119.2(4) yes . . . N(4) C(14) C(8) 118.9(4) yes . . . C(16) C(15) C(20) 117.2(6) yes . . . C(16) C(15) C(21) 121.4(4) yes . . . C(20) C(15) C(21) 121.4(4) yes . . . C(15) C(16) C(17) 121.9(4) yes . . . C(16) C(17) C(18) 120.6(4) yes . . . C(17) C(18) C(19) 118.4(6) yes . . . C(17) C(18) C(22) 121.1(4) yes . . . C(19) C(18) C(22) 120.5(4) yes . . . C(18) C(19) C(20) 121.2(4) yes . . . C(15) C(20) C(19) 120.8(5) yes . . . O(1) C(21) O(2) 123.7(6) yes . . . O(1) C(21) C(15) 118.2(4) yes . . . O(2) C(21) C(15) 118.1(4) yes . . . O(3) C(22) O(4) 123.2(6) yes . . . O(3) C(22) C(18) 118.0(4) yes . . . O(4) C(22) C(18) 118.8(4) yes . . . C(13) N(1) H(11) 121(5) no . . . C(13) N(1) H(12) 120(2) no . . . H(11) N(1) H(12) 118(6) no . . . C(13) N(2) H(13) 112(2) no . . . C(13) N(2) H(14) 117(5) no . . . H(13) N(2) H(14) 128(6) no . . . C(14) N(3) H(15) 118(5) no . . . C(14) N(3) H(16) 117(3) no . . . H(15) N(3) H(16) 125(6) no . . . C(14) N(4) H(17) 118(3) no . . . C(14) N(4) H(18) 123(4) no . . . H(17) N(4) H(18) 118(5) no . . . C(1) C(2) H(1) 119.2 no . . . C(3) C(2) H(1) 119.2 no . . . C(2) C(3) H(2) 118.5 no . . . C(4) C(3) H(2) 118.5 no . . . C(3) C(4) H(3) 122.1 no . . . C(11) C(4) H(3) 122.1 no . . . C(6) C(5) H(4) 122.3 no . . . C(10) C(5) H(4) 122.4 no . . . C(5) C(6) H(5) 118.7 no . . . C(7) C(6) H(5) 118.7 no . . . C(6) C(7) H(6) 119.0 no . . . C(8) C(7) H(6) 119.0 no . . . C(15) C(16) H(7) 119.1 no . . . C(17) C(16) H(7) 119.1 no . . . C(16) C(17) H(8) 119.7 no . . . C(18) C(17) H(8) 119.7 no . . . C(18) C(19) H(9) 119.4 no . . . C(20) C(19) H(9) 119.4 no . . . C(15) C(20) H(10) 119.6 no . . . C(19) C(20) H(10) 119.6 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(12) C(9) 177.5(6) ? . . . . C(2) C(1) C(12) C(11) -0.6(6) ? . . . . C(12) C(1) C(2) C(3) 0.7(6) ? . . . . C(2) C(1) C(13) N(1) -52.5(7) ? . . . . C(2) C(1) C(13) N(2) 127.0(5) ? . . . . C(13) C(1) C(2) C(3) -179.9(3) ? . . . . C(12) C(1) C(13) N(1) 126.9(5) ? . . . . C(12) C(1) C(13) N(2) -53.6(7) ? . . . . C(13) C(1) C(12) C(9) -1.9(10) ? . . . . C(13) C(1) C(12) C(11) -180.0(3) ? . . . . C(1) C(2) C(3) C(4) -0.4(7) ? . . . . C(2) C(3) C(4) C(11) -0.0(6) ? . . . . C(3) C(4) C(11) C(10) -178.1(6) ? . . . . C(3) C(4) C(11) C(12) 0.2(5) ? . . . . C(6) C(5) C(10) C(9) 1.0(7) ? . . . . C(6) C(5) C(10) C(11) 178.9(6) ? . . . . C(10) C(5) C(6) C(7) 0.0(7) ? . . . . C(5) C(6) C(7) C(8) -1.5(8) ? . . . . C(6) C(7) C(8) C(9) 1.9(7) ? . . . . C(6) C(7) C(8) C(14) -178.4(4) ? . . . . C(7) C(8) C(9) C(10) -0.9(6) ? . . . . C(7) C(8) C(9) C(12) 179.7(6) ? . . . . C(7) C(8) C(14) N(3) 120.9(5) ? . . . . C(7) C(8) C(14) N(4) -59.1(7) ? . . . . C(9) C(8) C(14) N(3) -59.4(7) ? . . . . C(9) C(8) C(14) N(4) 120.6(5) ? . . . . C(14) C(8) C(9) C(10) 179.4(4) ? . . . . C(14) C(8) C(9) C(12) -0.0(9) ? . . . . C(8) C(9) C(10) C(5) -0.6(7) ? . . . . C(8) C(9) C(10) C(11) -179.5(4) ? . . . . C(8) C(9) C(12) C(1) 0.9(13) ? . . . . C(8) C(9) C(12) C(11) 179.3(7) ? . . . . C(10) C(9) C(12) C(1) -178.7(7) ? . . . . C(10) C(9) C(12) C(11) -0.3(3) ? . . . . C(12) C(9) C(10) C(5) 179.1(4) ? . . . . C(12) C(9) C(10) C(11) 0.3(3) ? . . . . C(5) C(10) C(11) C(4) 0.1(12) ? . . . . C(5) C(10) C(11) C(12) -178.5(7) ? . . . . C(9) C(10) C(11) C(4) 178.3(7) ? . . . . C(9) C(10) C(11) C(12) -0.3(3) ? . . . . C(4) C(11) C(12) C(1) 0.1(5) ? . . . . C(4) C(11) C(12) C(9) -178.9(4) ? . . . . C(10) C(11) C(12) C(1) 179.2(4) ? . . . . C(10) C(11) C(12) C(9) 0.3(3) ? . . . . C(16) C(15) C(20) C(19) -0.8(8) ? . . . . C(20) C(15) C(16) C(17) -0.1(6) ? . . . . C(16) C(15) C(21) O(1) 12.6(7) ? . . . . C(16) C(15) C(21) O(2) -167.4(5) ? . . . . C(21) C(15) C(16) C(17) 178.4(5) ? . . . . C(20) C(15) C(21) O(1) -168.9(5) ? . . . . C(20) C(15) C(21) O(2) 11.1(7) ? . . . . C(21) C(15) C(20) C(19) -179.4(5) ? . . . . C(15) C(16) C(17) C(18) 0.2(6) ? . . . . C(16) C(17) C(18) C(19) 0.7(8) ? . . . . C(16) C(17) C(18) C(22) -179.3(5) ? . . . . C(17) C(18) C(19) C(20) -1.7(8) ? . . . . C(17) C(18) C(22) O(3) -4.3(7) ? . . . . C(17) C(18) C(22) O(4) 177.2(5) ? . . . . C(19) C(18) C(22) O(3) 175.7(5) ? . . . . C(19) C(18) C(22) O(4) -2.8(7) ? . . . . C(22) C(18) C(19) C(20) 178.4(5) ? . . . . C(18) C(19) C(20) C(15) 1.7(8) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) O(2) 2.223(4) ? . . O(1) O(5) 2.802(5) ? . 2_676 O(1) N(1) 2.898(5) ? . 2_665 O(1) N(3) 2.841(8) ? . . O(1) C(15) 2.365(7) ? . . O(1) C(16) 2.828(8) ? . . O(2) O(1) 2.223(4) ? . . O(2) O(5) 2.758(4) ? . . O(2) O(6) 2.878(7) ? . . O(2) N(3) 3.475(7) ? . . O(2) N(4) 2.826(8) ? . . O(2) C(14) 3.545(8) ? . . O(2) C(15) 2.359(8) ? . . O(2) C(20) 2.821(9) ? . . O(3) O(4) 2.210(4) ? . . O(3) O(6) 2.734(5) ? . 2_675 O(3) O(8) 2.86(3) ? . 2_675 O(3) N(1) 3.409(7) ? . 2_675 O(3) N(2) 2.793(8) ? . 2_675 O(3) C(13) 3.514(8) ? . 2_675 O(3) C(17) 2.817(9) ? . . O(3) C(18) 2.370(8) ? . . O(3) C(21) 3.491(6) ? . 2_675 O(4) O(3) 2.210(4) ? . . O(4) N(1) 3.531(7) ? . 1_565 O(4) N(1) 2.777(8) ? . 2_675 O(4) N(3) 2.794(5) ? . 1_565 O(4) C(7) 3.542(7) ? . 2_676 O(4) C(18) 2.368(7) ? . . O(4) C(19) 2.802(9) ? . . O(5) O(1) 2.802(5) ? . 2_676 O(5) O(2) 2.758(4) ? . . O(5) O(9) 2.719(6) ? . 1_455 O(5) C(2) 3.526(6) ? . 1_566 O(5) C(5) 3.364(9) ? . 1_565 O(5) C(21) 3.363(6) ? . 2_676 O(6) O(2) 2.878(7) ? . . O(6) O(3) 2.734(5) ? . 2_675 O(6) O(7) 2.669(8) ? . 1_455 O(6) O(8) 3.55(2) ? . . O(6) O(8) 3.29(3) ? . 2_575 O(6) C(4) 3.357(10) ? . 1_565 O(6) C(20) 3.464(8) ? . . O(6) C(21) 3.467(7) ? . . O(7) O(6) 2.669(8) ? . 1_655 O(7) O(8) 2.92(3) ? . 2_675 O(7) O(9) 2.846(6) ? . . O(7) O(9) 2.804(8) ? . 2_776 O(7) N(4) 2.835(6) ? . 2_676 O(8) O(3) 2.86(3) ? . 2_675 O(8) O(6) 3.55(2) ? . . O(8) O(6) 3.29(3) ? . 2_575 O(8) O(7) 2.92(3) ? . 2_675 O(8) O(8) 2.54(3) ? . 2_575 O(8) C(4) 3.34(3) ? . 2_565 O(8) C(17) 3.37(3) ? . 2_675 O(8) C(22) 3.41(2) ? . 2_675 O(9) O(5) 2.719(6) ? . 1_655 O(9) O(7) 2.846(6) ? . . O(9) O(7) 2.804(8) ? . 2_776 O(9) N(2) 2.923(6) ? . 2_676 O(9) C(9) 3.567(7) ? . 2_676 O(9) C(12) 3.553(6) ? . 2_676 N(1) O(1) 2.898(5) ? . 2_665 N(1) O(3) 3.409(7) ? . 2_675 N(1) O(4) 3.531(7) ? . 1_545 N(1) O(4) 2.777(8) ? . 2_675 N(1) N(2) 2.286(5) ? . . N(1) N(3) 3.480(7) ? . 2_665 N(1) C(1) 2.407(9) ? . . N(1) C(2) 3.035(9) ? . . N(1) C(12) 3.532(9) ? . . N(1) C(22) 3.467(9) ? . 2_675 N(2) O(3) 2.793(8) ? . 2_675 N(2) O(9) 2.923(6) ? . 2_676 N(2) N(1) 2.286(5) ? . . N(2) N(3) 3.285(7) ? . . N(2) C(1) 2.396(8) ? . . N(2) C(2) 3.537(8) ? . . N(2) C(12) 3.048(9) ? . . N(2) C(14) 3.431(7) ? . . N(3) O(1) 2.841(8) ? . . N(3) O(2) 3.475(7) ? . . N(3) O(4) 2.794(5) ? . 1_545 N(3) N(1) 3.480(7) ? . 2_665 N(3) N(2) 3.285(7) ? . . N(3) N(4) 2.283(5) ? . . N(3) C(7) 3.515(9) ? . . N(3) C(8) 2.403(9) ? . . N(3) C(9) 3.062(8) ? . . N(3) C(13) 3.509(7) ? . . N(3) C(21) 3.536(9) ? . . N(4) O(2) 2.826(8) ? . . N(4) O(7) 2.835(6) ? . 2_676 N(4) N(3) 2.283(5) ? . . N(4) C(7) 3.092(10) ? . . N(4) C(8) 2.410(8) ? . . N(4) C(9) 3.475(7) ? . . N(4) C(20) 3.531(8) ? . 2_676 C(1) N(1) 2.407(9) ? . . C(1) N(2) 2.396(8) ? . . C(1) C(3) 2.449(9) ? . . C(1) C(4) 2.886(10) ? . . C(1) C(9) 2.765(7) ? . . C(1) C(10) 3.421(9) ? . . C(1) C(11) 2.451(10) ? . . C(2) O(5) 3.526(6) ? . 1_544 C(2) N(1) 3.035(9) ? . . C(2) N(2) 3.537(8) ? . . C(2) C(2) 3.486(7) ? . 2_565 C(2) C(4) 2.439(11) ? . . C(2) C(11) 2.748(9) ? . . C(2) C(12) 2.361(7) ? . . C(2) C(13) 2.511(8) ? . . C(3) C(1) 2.449(9) ? . . C(3) C(11) 2.351(8) ? . . C(3) C(12) 2.735(7) ? . . C(4) O(6) 3.357(10) ? . 1_545 C(4) O(8) 3.34(3) ? . 2_565 C(4) C(1) 2.886(10) ? . . C(4) C(2) 2.439(11) ? . . C(4) C(9) 3.425(8) ? . . C(4) C(10) 2.756(7) ? . . C(4) C(12) 2.448(9) ? . . C(5) O(5) 3.364(9) ? . 1_545 C(5) C(5) 3.514(8) ? . 2_566 C(5) C(7) 2.435(10) ? . . C(5) C(8) 2.873(10) ? . . C(5) C(9) 2.442(10) ? . . C(5) C(10) 3.475(7) ? . 2_566 C(5) C(11) 2.740(9) ? . . C(5) C(12) 3.418(9) ? . . C(6) C(8) 2.431(11) ? . . C(6) C(9) 2.731(9) ? . . C(6) C(10) 2.349(8) ? . . C(7) O(4) 3.542(7) ? . 2_676 C(7) N(3) 3.515(9) ? . . C(7) N(4) 3.092(10) ? . . C(7) C(5) 2.435(10) ? . . C(7) C(9) 2.352(7) ? . . C(7) C(10) 2.732(8) ? . . C(7) C(14) 2.535(10) ? . . C(8) N(3) 2.403(9) ? . . C(8) N(4) 2.410(8) ? . . C(8) C(5) 2.873(10) ? . . C(8) C(6) 2.431(11) ? . . C(8) C(10) 2.432(8) ? . . C(8) C(11) 3.402(7) ? . . C(8) C(12) 2.754(7) ? . . C(9) O(9) 3.567(7) ? . 2_676 C(9) N(3) 3.062(8) ? . . C(9) N(4) 3.475(7) ? . . C(9) C(1) 2.765(7) ? . . C(9) C(4) 3.425(8) ? . . C(9) C(5) 2.442(10) ? . . C(9) C(6) 2.731(9) ? . . C(9) C(7) 2.352(7) ? . . C(9) C(11) 2.061(7) ? . . C(9) C(13) 3.489(8) ? . . C(9) C(14) 2.491(8) ? . . C(10) C(1) 3.421(9) ? . . C(10) C(4) 2.756(7) ? . . C(10) C(5) 3.475(7) ? . 2_566 C(10) C(6) 2.349(8) ? . . C(10) C(7) 2.732(8) ? . . C(10) C(8) 2.432(8) ? . . C(10) C(12) 2.066(9) ? . . C(11) C(1) 2.451(10) ? . . C(11) C(2) 2.748(9) ? . . C(11) C(3) 2.351(8) ? . . C(11) C(5) 2.740(9) ? . . C(11) C(8) 3.402(7) ? . . C(11) C(9) 2.061(7) ? . . C(12) O(9) 3.553(6) ? . 2_676 C(12) N(1) 3.532(9) ? . . C(12) N(2) 3.048(9) ? . . C(12) C(2) 2.361(7) ? . . C(12) C(3) 2.735(7) ? . . C(12) C(4) 2.448(9) ? . . C(12) C(5) 3.418(9) ? . . C(12) C(8) 2.754(7) ? . . C(12) C(10) 2.066(9) ? . . C(12) C(13) 2.504(9) ? . . C(12) C(14) 3.461(7) ? . . C(13) O(3) 3.514(8) ? . 2_675 C(13) N(3) 3.509(7) ? . . C(13) C(2) 2.511(8) ? . . C(13) C(9) 3.489(8) ? . . C(13) C(12) 2.504(9) ? . . C(14) O(2) 3.545(8) ? . . C(14) N(2) 3.431(7) ? . . C(14) C(7) 2.535(10) ? . . C(14) C(9) 2.491(8) ? . . C(14) C(12) 3.461(7) ? . . C(15) O(1) 2.365(7) ? . . C(15) O(2) 2.359(8) ? . . C(15) C(17) 2.419(9) ? . . C(15) C(18) 2.821(9) ? . . C(15) C(19) 2.428(9) ? . . C(16) O(1) 2.828(8) ? . . C(16) C(17) 3.586(8) ? . 2_675 C(16) C(18) 2.406(9) ? . . C(16) C(18) 3.451(7) ? . 2_675 C(16) C(19) 2.753(7) ? . . C(16) C(20) 2.390(6) ? . . C(16) C(21) 2.518(9) ? . . C(17) O(3) 2.817(9) ? . . C(17) O(8) 3.37(3) ? . 2_675 C(17) C(15) 2.419(9) ? . . C(17) C(16) 3.586(8) ? . 2_675 C(17) C(17) 3.494(8) ? . 2_675 C(17) C(19) 2.386(6) ? . . C(17) C(20) 2.763(7) ? . . C(17) C(22) 2.524(9) ? . . C(18) O(3) 2.370(8) ? . . C(18) O(4) 2.368(7) ? . . C(18) C(15) 2.821(9) ? . . C(18) C(16) 2.406(9) ? . . C(18) C(16) 3.451(7) ? . 2_675 C(18) C(20) 2.411(9) ? . . C(19) O(4) 2.802(9) ? . . C(19) C(15) 2.428(9) ? . . C(19) C(16) 2.753(7) ? . . C(19) C(17) 2.386(6) ? . . C(19) C(22) 2.498(9) ? . . C(20) O(2) 2.821(9) ? . . C(20) O(6) 3.464(8) ? . . C(20) N(4) 3.531(8) ? . 2_676 C(20) C(16) 2.390(6) ? . . C(20) C(17) 2.763(7) ? . . C(20) C(18) 2.411(9) ? . . C(20) C(21) 2.522(9) ? . . C(21) O(3) 3.491(6) ? . 2_675 C(21) O(5) 3.363(6) ? . 2_676 C(21) O(6) 3.467(7) ? . . C(21) N(3) 3.536(9) ? . . C(21) C(16) 2.518(9) ? . . C(21) C(20) 2.522(9) ? . . C(22) O(8) 3.41(2) ? . 2_675 C(22) N(1) 3.467(9) ? . 2_675 C(22) C(17) 2.524(9) ? . . C(22) C(19) 2.498(9) ? . . O(1) H(1) 3.552 ? . 2_665 O(1) H(7) 2.538 ? . . O(1) H(11) 2.20(4) ? . 2_665 O(1) H(12) 3.36(6) ? . 2_665 O(1) H(15) 3.43(9) ? . . O(1) H(16) 2.07(7) ? . . O(1) H(17) 3.07(7) ? . . O(2) H(10) 2.542 ? . . O(2) H(16) 2.89(6) ? . . O(2) H(17) 1.98(9) ? . . O(2) H(18) 3.36(7) ? . . O(3) H(6) 3.442 ? . 2_676 O(3) H(8) 2.525 ? . . O(3) H(12) 2.65(6) ? . 2_675 O(3) H(13) 1.80(8) ? . 2_675 O(3) H(14) 3.38(9) ? . 2_675 O(4) H(5) 3.436 ? . 2_676 O(4) H(6) 2.797 ? . 2_676 O(4) H(9) 2.501 ? . . O(4) H(11) 3.33(5) ? . 1_565 O(4) H(11) 3.16(7) ? . 2_675 O(4) H(12) 1.72(8) ? . 2_675 O(4) H(13) 2.96(6) ? . 2_675 O(4) H(15) 1.91(5) ? . 1_565 O(4) H(16) 3.13(5) ? . 1_565 O(5) H(1) 2.745 ? . 1_566 O(5) H(4) 2.729 ? . 1_565 O(5) H(5) 3.445 ? . 1_565 O(5) H(7) 3.471 ? . 2_676 O(5) H(10) 3.011 ? . . O(5) H(17) 3.16(6) ? . . O(6) H(3) 2.774 ? . 1_565 O(6) H(4) 3.498 ? . 1_565 O(6) H(8) 2.949 ? . 2_675 O(6) H(10) 3.124 ? . . O(6) H(13) 3.21(5) ? . . O(7) H(2) 3.517 ? . 2_665 O(7) H(17) 3.33(7) ? . 2_676 O(7) H(18) 1.97(5) ? . 2_676 O(8) H(2) 3.354 ? . 1_565 O(8) H(2) 3.576 ? . 2_565 O(8) H(3) 3.351 ? . 1_565 O(8) H(3) 2.468 ? . 2_565 O(8) H(6) 3.306 ? . 1_554 O(8) H(8) 2.954 ? . 2_675 O(9) H(1) 3.260 ? . 1_666 O(9) H(2) 3.014 ? . 1_666 O(9) H(4) 3.492 ? . 1_665 O(9) H(13) 3.57(6) ? . 2_676 O(9) H(14) 2.07(7) ? . 2_676 O(9) H(18) 3.33(5) ? . 2_676 N(1) H(1) 2.875 ? . . N(1) H(5) 3.019 ? . 1_554 N(1) H(12) 3.48(6) ? . 2_665 N(1) H(13) 2.38(5) ? . . N(1) H(14) 3.03(6) ? . . N(1) H(15) 3.24(8) ? . 2_665 N(1) H(16) 3.13(4) ? . 2_665 N(2) H(2) 3.000 ? . 2_565 N(2) H(11) 2.94(4) ? . . N(2) H(12) 2.53(5) ? . . N(2) H(15) 3.46(7) ? . . N(2) H(16) 3.36(5) ? . . N(3) H(9) 3.516 ? . 1_545 N(3) H(11) 3.23(6) ? . 2_665 N(3) H(12) 2.99(5) ? . 2_665 N(3) H(14) 3.48(7) ? . . N(3) H(17) 2.44(5) ? . . N(3) H(18) 3.10(4) ? . . N(4) H(6) 2.965 ? . . N(4) H(14) 3.56(7) ? . . N(4) H(15) 3.12(5) ? . . N(4) H(16) 2.39(4) ? . . C(1) H(1) 2.052 ? . . C(1) H(2) 3.285 ? . . C(1) H(7) 3.147 ? . 2_665 C(1) H(11) 2.51(6) ? . . C(1) H(12) 3.38(8) ? . . C(1) H(13) 3.24(7) ? . . C(1) H(14) 2.47(7) ? . . C(2) H(1) 3.433 ? . 2_565 C(2) H(2) 2.009 ? . . C(2) H(3) 3.290 ? . . C(2) H(7) 2.758 ? . 2_665 C(2) H(11) 2.91(6) ? . . C(3) H(1) 2.016 ? . . C(3) H(3) 2.054 ? . . C(3) H(7) 2.979 ? . 2_665 C(3) H(8) 3.263 ? . 2_665 C(3) H(14) 3.37(7) ? . 2_565 C(4) H(1) 3.273 ? . . C(4) H(2) 2.020 ? . . C(4) H(5) 3.367 ? . 2_566 C(4) H(7) 3.528 ? . 2_665 C(4) H(8) 3.103 ? . 2_665 C(5) H(4) 3.446 ? . 2_566 C(5) H(5) 2.039 ? . . C(5) H(6) 3.272 ? . . C(5) H(9) 3.516 ? . 1_545 C(5) H(10) 3.036 ? . 1_545 C(6) H(3) 3.443 ? . 2_566 C(6) H(4) 2.074 ? . . C(6) H(6) 1.997 ? . . C(6) H(10) 3.553 ? . 1_545 C(7) H(4) 3.286 ? . . C(7) H(5) 1.994 ? . . C(7) H(9) 3.514 ? . 1_545 C(7) H(18) 3.00(7) ? . . C(8) H(5) 3.269 ? . . C(8) H(6) 2.046 ? . . C(8) H(9) 3.057 ? . 1_545 C(8) H(15) 2.51(7) ? . . C(8) H(16) 3.10(7) ? . . C(8) H(17) 3.20(8) ? . . C(8) H(18) 2.58(5) ? . . C(9) H(4) 3.300 ? . . C(9) H(6) 3.203 ? . . C(9) H(9) 2.782 ? . 1_545 C(9) H(14) 3.32(9) ? . . C(9) H(15) 2.86(7) ? . . C(10) H(3) 3.139 ? . . C(10) H(4) 2.032 ? . . C(10) H(4) 3.199 ? . 2_566 C(10) H(5) 3.201 ? . . C(10) H(9) 3.040 ? . 1_545 C(10) H(10) 3.261 ? . 1_545 C(11) H(2) 3.203 ? . . C(11) H(3) 2.042 ? . . C(11) H(4) 3.123 ? . . C(11) H(4) 3.443 ? . 2_566 C(11) H(9) 3.469 ? . 1_545 C(12) H(1) 3.214 ? . . C(12) H(3) 3.306 ? . . C(12) H(9) 3.258 ? . 1_545 C(12) H(14) 2.85(9) ? . . C(12) H(15) 3.31(7) ? . . C(13) H(1) 2.667 ? . . C(13) H(2) 3.523 ? . 2_565 C(13) H(11) 1.80(4) ? . . C(13) H(12) 2.06(7) ? . . C(13) H(13) 1.92(7) ? . . C(13) H(14) 1.86(5) ? . . C(13) H(15) 3.32(7) ? . . C(14) H(6) 2.692 ? . . C(14) H(14) 3.29(8) ? . . C(14) H(15) 1.93(5) ? . . C(14) H(16) 1.79(6) ? . . C(14) H(17) 1.89(7) ? . . C(14) H(18) 1.95(4) ? . . C(15) H(7) 2.028 ? . . C(15) H(8) 3.262 ? . . C(15) H(9) 3.270 ? . . C(15) H(10) 2.038 ? . . C(15) H(17) 3.41(6) ? . 2_676 C(16) H(8) 2.009 ? . . C(16) H(10) 3.244 ? . . C(17) H(7) 2.003 ? . . C(17) H(9) 3.237 ? . . C(18) H(6) 2.958 ? . 2_676 C(18) H(7) 3.249 ? . . C(18) H(7) 3.480 ? . 2_675 C(18) H(8) 2.036 ? . . C(18) H(9) 2.014 ? . . C(18) H(10) 3.252 ? . . C(19) H(6) 3.101 ? . 2_676 C(19) H(8) 3.236 ? . . C(19) H(10) 2.026 ? . . C(19) H(15) 3.51(8) ? . 1_565 C(20) H(7) 3.241 ? . . C(20) H(8) 3.550 ? . 2_675 C(20) H(9) 2.024 ? . . C(20) H(17) 3.35(7) ? . 2_676 C(21) H(7) 2.669 ? . . C(21) H(10) 2.681 ? . . C(21) H(11) 3.36(4) ? . 2_665 C(21) H(16) 2.80(7) ? . . C(21) H(17) 2.85(8) ? . . C(22) H(6) 2.793 ? . 2_676 C(22) H(7) 3.499 ? . 2_675 C(22) H(8) 2.680 ? . . C(22) H(9) 2.644 ? . . C(22) H(12) 2.48(8) ? . 2_675 C(22) H(13) 2.70(7) ? . 2_675 C(22) H(15) 3.09(5) ? . 1_565 H(1) O(1) 3.552 ? . 2_665 H(1) O(5) 2.745 ? . 1_544 H(1) O(9) 3.260 ? . 1_444 H(1) N(1) 2.875 ? . . H(1) C(1) 2.052 ? . . H(1) C(2) 3.433 ? . 2_565 H(1) C(3) 2.016 ? . . H(1) C(4) 3.273 ? . . H(1) C(12) 3.214 ? . . H(1) C(13) 2.667 ? . . H(1) H(2) 2.290 ? . . H(1) H(5) 3.474 ? . 1_554 H(1) H(7) 2.957 ? . 2_665 H(1) H(11) 2.716 ? . . H(2) O(7) 3.517 ? . 2_665 H(2) O(8) 3.354 ? . 1_545 H(2) O(8) 3.576 ? . 2_565 H(2) O(9) 3.014 ? . 1_444 H(2) N(2) 3.000 ? . 2_565 H(2) C(1) 3.285 ? . . H(2) C(2) 2.009 ? . . H(2) C(4) 2.020 ? . . H(2) C(11) 3.203 ? . . H(2) C(13) 3.523 ? . 2_565 H(2) H(1) 2.290 ? . . H(2) H(3) 2.342 ? . . H(2) H(7) 3.297 ? . 2_665 H(2) H(8) 3.397 ? . 2_665 H(2) H(13) 3.193 ? . 2_565 H(2) H(14) 2.684 ? . 2_565 H(3) O(6) 2.774 ? . 1_545 H(3) O(8) 3.351 ? . 1_545 H(3) O(8) 2.468 ? . 2_565 H(3) C(2) 3.290 ? . . H(3) C(3) 2.054 ? . . H(3) C(6) 3.443 ? . 2_566 H(3) C(10) 3.139 ? . . H(3) C(11) 2.042 ? . . H(3) C(12) 3.306 ? . . H(3) H(2) 2.342 ? . . H(3) H(5) 3.200 ? . 2_566 H(3) H(8) 3.151 ? . 2_665 H(4) O(5) 2.729 ? . 1_545 H(4) O(6) 3.498 ? . 1_545 H(4) O(9) 3.492 ? . 1_445 H(4) C(5) 3.446 ? . 2_566 H(4) C(6) 2.074 ? . . H(4) C(7) 3.286 ? . . H(4) C(9) 3.300 ? . . H(4) C(10) 2.032 ? . . H(4) C(10) 3.199 ? . 2_566 H(4) C(11) 3.123 ? . . H(4) C(11) 3.443 ? . 2_566 H(4) H(5) 2.368 ? . . H(4) H(10) 3.085 ? . 1_545 H(5) O(4) 3.436 ? . 2_676 H(5) O(5) 3.445 ? . 1_545 H(5) N(1) 3.019 ? . 1_556 H(5) C(4) 3.367 ? . 2_566 H(5) C(5) 2.039 ? . . H(5) C(7) 1.994 ? . . H(5) C(8) 3.269 ? . . H(5) C(10) 3.201 ? . . H(5) H(1) 3.474 ? . 1_556 H(5) H(3) 3.200 ? . 2_566 H(5) H(4) 2.368 ? . . H(5) H(6) 2.272 ? . . H(5) H(11) 3.161 ? . 1_556 H(5) H(12) 2.936 ? . 1_556 H(5) H(15) 3.596 ? . 2_666 H(6) O(3) 3.442 ? . 2_676 H(6) O(4) 2.797 ? . 2_676 H(6) O(8) 3.306 ? . 1_556 H(6) N(4) 2.965 ? . . H(6) C(5) 3.272 ? . . H(6) C(6) 1.997 ? . . H(6) C(8) 2.046 ? . . H(6) C(9) 3.203 ? . . H(6) C(14) 2.692 ? . . H(6) C(18) 2.958 ? . 2_676 H(6) C(19) 3.101 ? . 2_676 H(6) C(22) 2.793 ? . 2_676 H(6) H(5) 2.272 ? . . H(6) H(9) 2.986 ? . 2_676 H(6) H(12) 3.519 ? . 1_556 H(6) H(15) 3.231 ? . 2_666 H(6) H(18) 2.843 ? . . H(7) O(1) 2.538 ? . . H(7) O(5) 3.471 ? . 2_676 H(7) C(1) 3.147 ? . 2_665 H(7) C(2) 2.758 ? . 2_665 H(7) C(3) 2.979 ? . 2_665 H(7) C(4) 3.528 ? . 2_665 H(7) C(15) 2.028 ? . . H(7) C(17) 2.003 ? . . H(7) C(18) 3.249 ? . . H(7) C(18) 3.480 ? . 2_675 H(7) C(20) 3.241 ? . . H(7) C(21) 2.669 ? . . H(7) C(22) 3.499 ? . 2_675 H(7) H(1) 2.957 ? . 2_665 H(7) H(2) 3.297 ? . 2_665 H(7) H(8) 2.293 ? . . H(7) H(11) 3.023 ? . 2_665 H(8) O(3) 2.525 ? . . H(8) O(6) 2.949 ? . 2_675 H(8) O(8) 2.954 ? . 2_675 H(8) C(3) 3.263 ? . 2_665 H(8) C(4) 3.103 ? . 2_665 H(8) C(15) 3.262 ? . . H(8) C(16) 2.009 ? . . H(8) C(18) 2.036 ? . . H(8) C(19) 3.236 ? . . H(8) C(20) 3.550 ? . 2_675 H(8) C(22) 2.680 ? . . H(8) H(2) 3.397 ? . 2_665 H(8) H(3) 3.151 ? . 2_665 H(8) H(7) 2.293 ? . . H(9) O(4) 2.501 ? . . H(9) N(3) 3.516 ? . 1_565 H(9) C(5) 3.516 ? . 1_565 H(9) C(7) 3.514 ? . 1_565 H(9) C(8) 3.057 ? . 1_565 H(9) C(9) 2.782 ? . 1_565 H(9) C(10) 3.040 ? . 1_565 H(9) C(11) 3.469 ? . 1_565 H(9) C(12) 3.258 ? . 1_565 H(9) C(15) 3.270 ? . . H(9) C(17) 3.237 ? . . H(9) C(18) 2.014 ? . . H(9) C(20) 2.024 ? . . H(9) C(22) 2.644 ? . . H(9) H(6) 2.986 ? . 2_676 H(9) H(10) 2.316 ? . . H(9) H(15) 2.731 ? . 1_565 H(10) O(2) 2.542 ? . . H(10) O(5) 3.011 ? . . H(10) O(6) 3.124 ? . . H(10) C(5) 3.036 ? . 1_565 H(10) C(6) 3.553 ? . 1_565 H(10) C(10) 3.261 ? . 1_565 H(10) C(15) 2.038 ? . . H(10) C(16) 3.244 ? . . H(10) C(18) 3.252 ? . . H(10) C(19) 2.026 ? . . H(10) C(21) 2.681 ? . . H(10) H(4) 3.085 ? . 1_565 H(10) H(9) 2.316 ? . . H(10) H(17) 3.512 ? . 2_676 H(11) O(1) 2.20(4) ? . 2_665 H(11) O(4) 3.33(5) ? . 1_545 H(11) O(4) 3.16(7) ? . 2_675 H(11) N(2) 2.94(4) ? . . H(11) N(3) 3.23(6) ? . 2_665 H(11) C(1) 2.51(6) ? . . H(11) C(2) 2.91(6) ? . . H(11) C(13) 1.80(4) ? . . H(11) C(21) 3.36(4) ? . 2_665 H(11) H(1) 2.716 ? . . H(11) H(5) 3.161 ? . 1_554 H(11) H(7) 3.023 ? . 2_665 H(11) H(12) 1.55(10) ? . . H(11) H(12) 3.43(8) ? . 2_665 H(11) H(13) 3.10(7) ? . . H(11) H(15) 3.19(11) ? . 2_665 H(11) H(16) 2.75(7) ? . 2_665 H(12) O(1) 3.36(6) ? . 2_665 H(12) O(3) 2.65(6) ? . 2_675 H(12) O(4) 1.72(8) ? . 2_675 H(12) N(1) 3.48(6) ? . 2_665 H(12) N(2) 2.53(5) ? . . H(12) N(3) 2.99(5) ? . 2_665 H(12) C(1) 3.38(8) ? . . H(12) C(13) 2.06(7) ? . . H(12) C(22) 2.48(8) ? . 2_675 H(12) H(5) 2.936 ? . 1_554 H(12) H(6) 3.519 ? . 1_554 H(12) H(11) 1.55(10) ? . . H(12) H(11) 3.43(8) ? . 2_665 H(12) H(12) 3.36(9) ? . 2_665 H(12) H(13) 2.19(6) ? . . H(12) H(14) 3.38(9) ? . . H(12) H(15) 2.51(9) ? . 2_665 H(12) H(16) 2.88(6) ? . 2_665 H(13) O(3) 1.80(8) ? . 2_675 H(13) O(4) 2.96(6) ? . 2_675 H(13) O(6) 3.21(5) ? . . H(13) O(9) 3.57(6) ? . 2_676 H(13) N(1) 2.38(5) ? . . H(13) C(1) 3.24(7) ? . . H(13) C(13) 1.92(7) ? . . H(13) C(22) 2.70(7) ? . 2_675 H(13) H(2) 3.193 ? . 2_565 H(13) H(11) 3.10(7) ? . . H(13) H(12) 2.19(6) ? . . H(13) H(14) 1.66(12) ? . . H(13) H(16) 3.51(8) ? . . H(14) O(3) 3.38(9) ? . 2_675 H(14) O(9) 2.07(7) ? . 2_676 H(14) N(1) 3.03(6) ? . . H(14) N(3) 3.48(7) ? . . H(14) N(4) 3.56(7) ? . . H(14) C(1) 2.47(7) ? . . H(14) C(3) 3.37(7) ? . 2_565 H(14) C(9) 3.32(9) ? . . H(14) C(12) 2.85(9) ? . . H(14) C(13) 1.86(5) ? . . H(14) C(14) 3.29(8) ? . . H(14) H(2) 2.684 ? . 2_565 H(14) H(12) 3.38(9) ? . . H(14) H(13) 1.66(12) ? . . H(15) O(1) 3.43(9) ? . . H(15) O(4) 1.91(5) ? . 1_545 H(15) N(1) 3.24(7) ? . 2_665 H(15) N(2) 3.46(7) ? . . H(15) N(4) 3.12(5) ? . . H(15) C(8) 2.51(7) ? . . H(15) C(9) 2.86(7) ? . . H(15) C(12) 3.31(7) ? . . H(15) C(13) 3.32(7) ? . . H(15) C(14) 1.93(5) ? . . H(15) C(19) 3.51(8) ? . 1_545 H(15) C(22) 3.09(5) ? . 1_545 H(15) H(5) 3.596 ? . 2_666 H(15) H(6) 3.231 ? . 2_666 H(15) H(9) 2.731 ? . 1_545 H(15) H(11) 3.19(11) ? . 2_665 H(15) H(12) 2.51(9) ? . 2_665 H(15) H(16) 1.53(10) ? . . H(15) H(17) 3.36(8) ? . . H(16) O(1) 2.07(7) ? . . H(16) O(2) 2.89(6) ? . . H(16) O(4) 3.13(5) ? . 1_545 H(16) N(1) 3.13(4) ? . 2_665 H(16) N(2) 3.36(5) ? . . H(16) N(4) 2.39(4) ? . . H(16) C(8) 3.10(7) ? . . H(16) C(14) 1.79(6) ? . . H(16) C(21) 2.80(7) ? . . H(16) H(11) 2.75(7) ? . 2_665 H(16) H(12) 2.88(6) ? . 2_665 H(16) H(13) 3.51(8) ? . . H(16) H(15) 1.53(10) ? . . H(16) H(17) 2.25(6) ? . . H(16) H(18) 3.27(7) ? . . H(17) O(1) 3.07(7) ? . . H(17) O(2) 1.98(9) ? . . H(17) O(5) 3.16(6) ? . . H(17) O(7) 3.33(7) ? . 2_676 H(17) N(3) 2.44(5) ? . . H(17) C(8) 3.20(8) ? . . H(17) C(14) 1.89(7) ? . . H(17) C(15) 3.41(6) ? . 2_676 H(17) C(20) 3.35(6) ? . 2_676 H(17) C(21) 2.85(8) ? . . H(17) H(10) 3.512 ? . 2_676 H(17) H(15) 3.36(8) ? . . H(17) H(16) 2.25(6) ? . . H(17) H(18) 1.52(10) ? . . H(18) O(2) 3.36(7) ? . . H(18) O(7) 1.97(5) ? . 2_676 H(18) O(9) 3.33(6) ? . 2_676 H(18) N(3) 3.10(4) ? . . H(18) C(7) 3.00(7) ? . . H(18) C(8) 2.58(5) ? . . H(18) C(14) 1.95(4) ? . . H(18) H(6) 2.843 ? . . H(18) H(16) 3.27(7) ? . . H(18) H(17) 1.52(10) ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__Cytidine_(Rigaku_Master_f _database_code_depnum_ccdc_archive 'CCDC 920481' #TrackingRef '16984_web_deposit_cif_file_0_TakahiroKusukawa_1358506581.1c2_2a2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H28 N4 O8 ' _chemical_formula_moiety 'C24 H28 N4 O8 ' _chemical_formula_weight 500.51 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.6126(14) _cell_length_b 12.017(2) _cell_length_c 10.144(2) _cell_angle_alpha 108.959(14) _cell_angle_beta 94.679(15) _cell_angle_gamma 114.816(11) _cell_volume 1175.4(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 25.1 _cell_measurement_theta_max 29.0 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528.00 _exptl_absorpt_coefficient_mu 0.904 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_T_max 0.914 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 5778 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_theta_max 67.24 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.24 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -4.45 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4211 _reflns_number_gt 2364 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.2518 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4211 _refine_ls_number_parameters 338 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1261P)^2^+1.2237P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 1.74 _refine_diff_density_min -0.57 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 0.7637(2) 0.4312(3) 0.2322(4) 0.0386(8) Uani 1.00 1 d . . . O(2) O 0.7844(3) 0.2898(3) 0.3151(4) 0.0425(9) Uani 1.00 1 d . . . O(3) O 1.4250(3) 0.7091(3) 0.2343(3) 0.0376(8) Uani 1.00 1 d . . . O(4) O 1.4460(2) 0.5526(3) 0.2894(3) 0.0362(7) Uani 1.00 1 d . . . O(5) O 0.6057(3) 0.0704(3) 0.6178(3) 0.0393(8) Uiso 1.00 1 d . . . O(6) O 1.6465(5) 0.9982(5) 0.1093(5) 0.0831(14) Uiso 1.00 1 d . . . O(7) O 1.3869(5) 0.8108(6) 0.0168(6) 0.0966(17) Uiso 1.00 1 d . . . O(8) O 0.7837(6) 0.1222(6) 0.4435(7) 0.115(2) Uiso 1.00 1 d . . . N(1) N 0.3217(4) 0.3896(4) -0.1808(4) 0.0343(9) Uani 1.00 1 d . . . N(2) N 0.3438(4) 0.2187(4) -0.1551(4) 0.0334(9) Uani 1.00 1 d . . . N(3) N 0.5203(3) 0.3648(4) 0.3098(4) 0.0301(8) Uani 1.00 1 d . . . N(4) N 0.5177(3) 0.1792(4) 0.3289(4) 0.0352(9) Uani 1.00 1 d . . . C(1) C 0.1503(3) 0.2408(4) -0.1079(4) 0.0260(9) Uani 1.00 1 d . . . C(2) C 0.0472(4) 0.2285(4) -0.1956(4) 0.0293(9) Uani 1.00 1 d . . . C(3) C -0.0787(4) 0.1804(4) -0.1703(5) 0.0319(10) Uani 1.00 1 d . . . C(4) C -0.0985(3) 0.1470(4) -0.0550(4) 0.0278(9) Uani 1.00 1 d . . . C(5) C 0.0694(4) 0.1142(4) 0.3830(4) 0.0305(10) Uani 1.00 1 d . . . C(6) C 0.1676(4) 0.1239(4) 0.4748(4) 0.0295(9) Uani 1.00 1 d . . . C(7) C 0.2945(4) 0.1679(4) 0.4506(4) 0.0300(9) Uani 1.00 1 d . . . C(8) C 0.3215(3) 0.2020(4) 0.3373(4) 0.0252(8) Uani 1.00 1 d . . . C(9) C 0.2383(3) 0.2219(4) 0.1144(4) 0.0243(8) Uani 1.00 1 d . . . C(10) C -0.0108(3) 0.1305(4) 0.1625(4) 0.0258(9) Uani 1.00 1 d . . . C(11) C 0.2191(3) 0.1910(4) 0.2355(4) 0.0242(8) Uani 1.00 1 d . . . C(12) C 0.0905(3) 0.1443(3) 0.2597(4) 0.0234(8) Uani 1.00 1 d . . . C(13) C 0.1361(3) 0.2080(3) 0.0169(4) 0.0230(8) Uani 1.00 1 d . . . C(14) C 0.0079(3) 0.1608(3) 0.0428(4) 0.0237(8) Uani 1.00 1 d . . . C(15) C 0.2781(4) 0.2852(4) -0.1479(4) 0.0272(9) Uani 1.00 1 d . . . C(16) C 0.4590(3) 0.2505(4) 0.3236(4) 0.0249(8) Uani 1.00 1 d . . . C(17) C 0.9743(3) 0.4447(4) 0.2778(4) 0.0264(9) Uani 1.00 1 d . . . C(18) C 1.0198(4) 0.5145(4) 0.1911(5) 0.0311(9) Uani 1.00 1 d . . . C(19) C 1.1503(4) 0.5665(4) 0.1878(5) 0.0337(10) Uani 1.00 1 d . . . C(20) C 1.2380(3) 0.5499(4) 0.2709(4) 0.0259(9) Uani 1.00 1 d . . . C(21) C 1.1936(3) 0.4803(4) 0.3577(4) 0.0273(9) Uani 1.00 1 d . . . C(22) C 1.0625(3) 0.4284(4) 0.3611(4) 0.0270(9) Uani 1.00 1 d . . . C(23) C 0.8306(4) 0.3840(4) 0.2744(4) 0.0281(9) Uani 1.00 1 d . . . C(24) C 1.3804(4) 0.6075(4) 0.2654(4) 0.0278(9) Uani 1.00 1 d . . . H(1) H 0.0599 0.2526 -0.2747 0.035 Uiso 1.00 1 c R . . H(2) H -0.1492 0.1712 -0.2332 0.038 Uiso 1.00 1 c R . . H(3) H -0.1829 0.1145 -0.0393 0.033 Uiso 1.00 1 c R . . H(4) H -0.0142 0.0872 0.4009 0.037 Uiso 1.00 1 c R . . H(5) H 0.1517 0.1015 0.5545 0.035 Uiso 1.00 1 c R . . H(6) H 0.3620 0.1737 0.5147 0.036 Uiso 1.00 1 c R . . H(7) H 0.3227 0.2529 0.0983 0.029 Uiso 1.00 1 c R . . H(8) H -0.0951 0.0994 0.1785 0.031 Uiso 1.00 1 c R . . H(9) H 0.9614 0.5264 0.1344 0.037 Uiso 1.00 1 c R . . H(10) H 1.1798 0.6135 0.1289 0.040 Uiso 1.00 1 c R . . H(11) H 1.2522 0.4682 0.4141 0.033 Uiso 1.00 1 c R . . H(12) H 1.0331 0.3819 0.4204 0.032 Uiso 1.00 1 c R . . H(13) H 0.274(5) 0.433(5) -0.186(5) 0.037(13) Uiso 1.00 1 c . . . H(14) H 0.387(4) 0.414(4) -0.212(5) 0.027(12) Uiso 1.00 1 c . . . H(15) H 0.306(4) 0.146(4) -0.139(5) 0.030(12) Uiso 1.00 1 c . . . H(16) H 0.425(7) 0.251(7) -0.185(7) 0.08(2) Uiso 1.00 1 c . . . H(17) H 0.606(5) 0.397(5) 0.304(5) 0.039(13) Uiso 1.00 1 c . . . H(18) H 0.482(5) 0.415(6) 0.315(6) 0.060(18) Uiso 1.00 1 c . . . H(19) H 0.609(5) 0.222(5) 0.321(5) 0.046(15) Uiso 1.00 1 c . . . H(20) H 0.476(5) 0.094(5) 0.330(5) 0.050(15) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0222(15) 0.0432(18) 0.067(2) 0.0187(14) 0.0163(15) 0.0353(17) O(2) 0.0272(16) 0.049(2) 0.069(2) 0.0182(15) 0.0188(16) 0.0432(19) O(3) 0.0293(16) 0.0362(17) 0.062(2) 0.0176(14) 0.0231(15) 0.0307(16) O(4) 0.0233(15) 0.0364(17) 0.063(2) 0.0175(13) 0.0173(14) 0.0300(16) N(1) 0.029(2) 0.039(2) 0.052(2) 0.0197(18) 0.0222(19) 0.031(2) N(2) 0.033(2) 0.038(2) 0.050(2) 0.0234(18) 0.0231(18) 0.0306(19) N(3) 0.0194(18) 0.039(2) 0.043(2) 0.0154(17) 0.0131(16) 0.0255(18) N(4) 0.025(2) 0.038(2) 0.054(2) 0.0165(17) 0.0140(18) 0.029(2) C(1) 0.023(2) 0.027(2) 0.030(2) 0.0118(17) 0.0098(17) 0.0129(17) C(2) 0.029(2) 0.034(2) 0.033(2) 0.0193(19) 0.0089(18) 0.0167(19) C(3) 0.022(2) 0.033(2) 0.041(2) 0.0141(18) 0.0006(18) 0.015(2) C(4) 0.0139(18) 0.029(2) 0.040(2) 0.0096(16) 0.0073(17) 0.0132(19) C(5) 0.027(2) 0.029(2) 0.038(2) 0.0100(19) 0.0157(19) 0.020(2) C(6) 0.029(2) 0.031(2) 0.031(2) 0.0100(18) 0.0135(18) 0.0204(19) C(7) 0.027(2) 0.033(2) 0.031(2) 0.0129(19) 0.0059(18) 0.0164(19) C(8) 0.024(2) 0.023(2) 0.033(2) 0.0113(16) 0.0109(17) 0.0145(17) C(9) 0.0156(18) 0.028(2) 0.031(2) 0.0089(16) 0.0094(16) 0.0149(18) C(10) 0.0200(19) 0.025(2) 0.036(2) 0.0113(17) 0.0137(17) 0.0133(18) C(11) 0.0212(19) 0.024(2) 0.026(2) 0.0092(16) 0.0093(16) 0.0105(17) C(12) 0.0193(19) 0.0196(19) 0.032(2) 0.0076(16) 0.0098(16) 0.0120(17) C(13) 0.0191(19) 0.0214(19) 0.030(2) 0.0103(16) 0.0078(16) 0.0115(17) C(14) 0.0204(19) 0.0216(19) 0.033(2) 0.0108(16) 0.0085(16) 0.0132(17) C(15) 0.024(2) 0.030(2) 0.028(2) 0.0119(18) 0.0071(17) 0.0141(18) C(16) 0.0206(19) 0.031(2) 0.031(2) 0.0128(17) 0.0080(16) 0.0207(18) C(17) 0.0197(19) 0.026(2) 0.032(2) 0.0103(17) 0.0065(16) 0.0107(18) C(18) 0.026(2) 0.036(2) 0.039(2) 0.0167(19) 0.0083(18) 0.020(2) C(19) 0.030(2) 0.037(2) 0.045(2) 0.016(2) 0.014(2) 0.027(2) C(20) 0.021(2) 0.026(2) 0.030(2) 0.0096(17) 0.0076(16) 0.0106(17) C(21) 0.022(2) 0.033(2) 0.033(2) 0.0153(18) 0.0097(17) 0.0158(19) C(22) 0.023(2) 0.029(2) 0.035(2) 0.0132(17) 0.0128(17) 0.0170(19) C(23) 0.024(2) 0.029(2) 0.034(2) 0.0124(18) 0.0087(17) 0.0156(19) C(24) 0.026(2) 0.028(2) 0.034(2) 0.0142(18) 0.0114(17) 0.0141(18) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(23) 1.259(7) yes . . O(2) C(23) 1.253(6) yes . . O(3) C(24) 1.268(6) yes . . O(4) C(24) 1.253(7) yes . . N(1) C(15) 1.307(7) yes . . N(2) C(15) 1.307(8) yes . . N(3) C(16) 1.317(6) yes . . N(4) C(16) 1.310(8) yes . . C(1) C(2) 1.356(7) yes . . C(1) C(13) 1.446(7) yes . . C(1) C(15) 1.492(6) yes . . C(2) C(3) 1.409(6) yes . . C(3) C(4) 1.361(7) yes . . C(4) C(14) 1.435(6) yes . . C(5) C(6) 1.352(7) yes . . C(5) C(12) 1.423(7) yes . . C(6) C(7) 1.414(6) yes . . C(7) C(8) 1.358(7) yes . . C(8) C(11) 1.441(6) yes . . C(8) C(16) 1.489(6) yes . . C(9) C(11) 1.403(7) yes . . C(9) C(13) 1.396(6) yes . . C(10) C(12) 1.386(6) yes . . C(10) C(14) 1.385(7) yes . . C(11) C(12) 1.432(6) yes . . C(13) C(14) 1.435(6) yes . . C(17) C(18) 1.392(7) yes . . C(17) C(22) 1.391(7) yes . . C(17) C(23) 1.507(6) yes . . C(18) C(19) 1.384(6) yes . . C(19) C(20) 1.388(8) yes . . C(20) C(21) 1.390(7) yes . . C(20) C(24) 1.516(6) yes . . C(21) C(22) 1.391(6) yes . . N(1) H(13) 0.92(7) no . . N(1) H(14) 0.82(5) no . . N(2) H(15) 0.88(5) no . . N(2) H(16) 0.97(7) no . . N(3) H(17) 0.92(6) no . . N(3) H(18) 0.88(8) no . . N(4) H(19) 0.99(5) no . . N(4) H(20) 0.94(6) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.940 no . . C(10) H(8) 0.940 no . . C(18) H(9) 0.940 no . . C(19) H(10) 0.940 no . . C(21) H(11) 0.940 no . . C(22) H(12) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(13) 121.4(4) yes . . . C(2) C(1) C(15) 117.4(4) yes . . . C(13) C(1) C(15) 121.2(4) yes . . . C(1) C(2) C(3) 121.2(5) yes . . . C(2) C(3) C(4) 120.2(4) yes . . . C(3) C(4) C(14) 120.8(4) yes . . . C(6) C(5) C(12) 121.1(4) yes . . . C(5) C(6) C(7) 119.8(4) yes . . . C(6) C(7) C(8) 121.8(4) yes . . . C(7) C(8) C(11) 120.2(4) yes . . . C(7) C(8) C(16) 117.6(4) yes . . . C(11) C(8) C(16) 122.2(4) yes . . . C(11) C(9) C(13) 122.1(3) yes . . . C(12) C(10) C(14) 122.4(4) yes . . . C(8) C(11) C(9) 123.7(3) yes . . . C(8) C(11) C(12) 117.6(4) yes . . . C(9) C(11) C(12) 118.7(4) yes . . . C(5) C(12) C(10) 121.4(4) yes . . . C(5) C(12) C(11) 119.6(4) yes . . . C(10) C(12) C(11) 119.0(4) yes . . . C(1) C(13) C(9) 124.6(3) yes . . . C(1) C(13) C(14) 117.0(4) yes . . . C(9) C(13) C(14) 118.4(4) yes . . . C(4) C(14) C(10) 121.1(4) yes . . . C(4) C(14) C(13) 119.4(4) yes . . . C(10) C(14) C(13) 119.4(4) yes . . . N(1) C(15) N(2) 120.1(4) yes . . . N(1) C(15) C(1) 118.9(5) yes . . . N(2) C(15) C(1) 121.0(4) yes . . . N(3) C(16) N(4) 121.2(4) yes . . . N(3) C(16) C(8) 119.9(5) yes . . . N(4) C(16) C(8) 118.8(4) yes . . . C(18) C(17) C(22) 118.8(4) yes . . . C(18) C(17) C(23) 119.4(4) yes . . . C(22) C(17) C(23) 121.7(4) yes . . . C(17) C(18) C(19) 120.6(5) yes . . . C(18) C(19) C(20) 120.5(5) yes . . . C(19) C(20) C(21) 119.4(4) yes . . . C(19) C(20) C(24) 119.6(4) yes . . . C(21) C(20) C(24) 121.0(4) yes . . . C(20) C(21) C(22) 119.9(4) yes . . . C(17) C(22) C(21) 120.8(4) yes . . . O(1) C(23) O(2) 123.5(4) yes . . . O(1) C(23) C(17) 118.4(4) yes . . . O(2) C(23) C(17) 118.1(5) yes . . . O(3) C(24) O(4) 124.1(4) yes . . . O(3) C(24) C(20) 116.6(4) yes . . . O(4) C(24) C(20) 119.3(4) yes . . . C(15) N(1) H(13) 122(3) no . . . C(15) N(1) H(14) 123(4) no . . . H(13) N(1) H(14) 114(5) no . . . C(15) N(2) H(15) 115(4) no . . . C(15) N(2) H(16) 117(5) no . . . H(15) N(2) H(16) 127(6) no . . . C(16) N(3) H(17) 121(4) no . . . C(16) N(3) H(18) 119(4) no . . . H(17) N(3) H(18) 120(5) no . . . C(16) N(4) H(19) 112(4) no . . . C(16) N(4) H(20) 124(4) no . . . H(19) N(4) H(20) 123(6) no . . . C(1) C(2) H(1) 119.4 no . . . C(3) C(2) H(1) 119.4 no . . . C(2) C(3) H(2) 119.9 no . . . C(4) C(3) H(2) 119.9 no . . . C(3) C(4) H(3) 119.6 no . . . C(14) C(4) H(3) 119.6 no . . . C(6) C(5) H(4) 119.5 no . . . C(12) C(5) H(4) 119.5 no . . . C(5) C(6) H(5) 120.1 no . . . C(7) C(6) H(5) 120.1 no . . . C(6) C(7) H(6) 119.1 no . . . C(8) C(7) H(6) 119.1 no . . . C(11) C(9) H(7) 119.0 no . . . C(13) C(9) H(7) 119.0 no . . . C(12) C(10) H(8) 118.8 no . . . C(14) C(10) H(8) 118.8 no . . . C(17) C(18) H(9) 119.7 no . . . C(19) C(18) H(9) 119.7 no . . . C(18) C(19) H(10) 119.8 no . . . C(20) C(19) H(10) 119.8 no . . . C(20) C(21) H(11) 120.0 no . . . C(22) C(21) H(11) 120.0 no . . . C(17) C(22) H(12) 119.6 no . . . C(21) C(22) H(12) 119.6 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(13) C(9) -178.0(4) ? . . . . C(2) C(1) C(13) C(14) 0.6(6) ? . . . . C(13) C(1) C(2) C(3) -1.5(6) ? . . . . C(2) C(1) C(15) N(1) 48.5(5) ? . . . . C(2) C(1) C(15) N(2) -129.1(4) ? . . . . C(15) C(1) C(2) C(3) 176.5(4) ? . . . . C(13) C(1) C(15) N(1) -133.4(4) ? . . . . C(13) C(1) C(15) N(2) 48.9(5) ? . . . . C(15) C(1) C(13) C(9) 4.1(6) ? . . . . C(15) C(1) C(13) C(14) -177.3(3) ? . . . . C(1) C(2) C(3) C(4) 1.0(7) ? . . . . C(2) C(3) C(4) C(14) 0.3(6) ? . . . . C(3) C(4) C(14) C(10) 178.2(4) ? . . . . C(3) C(4) C(14) C(13) -1.2(6) ? . . . . C(6) C(5) C(12) C(10) 177.9(4) ? . . . . C(6) C(5) C(12) C(11) -2.7(6) ? . . . . C(12) C(5) C(6) C(7) 1.7(6) ? . . . . C(5) C(6) C(7) C(8) 0.4(7) ? . . . . C(6) C(7) C(8) C(11) -1.5(6) ? . . . . C(6) C(7) C(8) C(16) 178.4(4) ? . . . . C(7) C(8) C(11) C(9) -178.8(4) ? . . . . C(7) C(8) C(11) C(12) 0.4(6) ? . . . . C(7) C(8) C(16) N(3) -127.3(4) ? . . . . C(7) C(8) C(16) N(4) 51.2(5) ? . . . . C(11) C(8) C(16) N(3) 52.5(5) ? . . . . C(11) C(8) C(16) N(4) -128.9(4) ? . . . . C(16) C(8) C(11) C(9) 1.3(6) ? . . . . C(16) C(8) C(11) C(12) -179.4(3) ? . . . . C(11) C(9) C(13) C(1) 178.6(4) ? . . . . C(11) C(9) C(13) C(14) 0.1(5) ? . . . . C(13) C(9) C(11) C(8) 179.0(4) ? . . . . C(13) C(9) C(11) C(12) -0.2(5) ? . . . . C(12) C(10) C(14) C(4) -179.3(4) ? . . . . C(12) C(10) C(14) C(13) 0.1(5) ? . . . . C(14) C(10) C(12) C(5) 179.2(4) ? . . . . C(14) C(10) C(12) C(11) -0.3(5) ? . . . . C(8) C(11) C(12) C(5) 1.6(6) ? . . . . C(8) C(11) C(12) C(10) -179.0(3) ? . . . . C(9) C(11) C(12) C(5) -179.1(4) ? . . . . C(9) C(11) C(12) C(10) 0.3(5) ? . . . . C(1) C(13) C(14) C(4) 0.7(5) ? . . . . C(1) C(13) C(14) C(10) -178.7(3) ? . . . . C(9) C(13) C(14) C(4) 179.4(3) ? . . . . C(9) C(13) C(14) C(10) -0.0(5) ? . . . . C(18) C(17) C(22) C(21) -0.3(6) ? . . . . C(22) C(17) C(18) C(19) 0.1(4) ? . . . . C(18) C(17) C(23) O(1) -22.4(5) ? . . . . C(18) C(17) C(23) O(2) 158.2(4) ? . . . . C(23) C(17) C(18) C(19) -177.3(4) ? . . . . C(22) C(17) C(23) O(1) 160.2(4) ? . . . . C(22) C(17) C(23) O(2) -19.2(5) ? . . . . C(23) C(17) C(22) C(21) 177.1(3) ? . . . . C(17) C(18) C(19) C(20) 0.0(6) ? . . . . C(18) C(19) C(20) C(21) 0.0(5) ? . . . . C(18) C(19) C(20) C(24) 179.9(3) ? . . . . C(19) C(20) C(21) C(22) -0.2(5) ? . . . . C(19) C(20) C(24) O(3) 27.4(5) ? . . . . C(19) C(20) C(24) O(4) -151.7(4) ? . . . . C(21) C(20) C(24) O(3) -152.8(4) ? . . . . C(21) C(20) C(24) O(4) 28.2(5) ? . . . . C(24) C(20) C(21) C(22) 179.9(3) ? . . . . C(20) C(21) C(22) C(17) 0.4(6) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) O(7) 2.851(5) ? . 2_765 O(1) N(1) 2.886(7) ? . 2_665 O(1) N(3) 2.849(5) ? . . O(2) O(6) 3.032(5) ? . 1_445 O(2) O(7) 3.316(7) ? . 2_765 O(2) O(8) 2.728(10) ? . . O(2) N(3) 3.542(6) ? . . O(2) N(4) 2.849(5) ? . . O(2) C(21) 3.468(5) ? . 2_766 O(2) C(22) 3.490(4) ? . 2_766 O(3) O(5) 2.774(5) ? . 2_766 O(3) O(7) 2.933(9) ? . . O(3) N(2) 2.730(5) ? . 2_765 O(4) N(1) 2.895(5) ? . 2_765 O(4) N(2) 3.565(6) ? . 2_765 O(4) N(3) 2.790(7) ? . 1_655 O(4) C(7) 3.430(4) ? . 2_766 O(4) C(9) 3.381(4) ? . 1_655 O(5) O(3) 2.774(5) ? . 2_766 O(5) O(5) 2.744(4) ? . 2_656 O(5) O(7) 3.492(7) ? . 2_766 O(5) O(8) 2.831(8) ? . . O(5) N(4) 2.986(6) ? . 2_656 O(5) C(3) 3.550(5) ? . 1_656 O(5) C(7) 3.413(7) ? . 2_656 O(5) C(24) 3.589(6) ? . 2_766 O(6) O(2) 3.032(5) ? . 1_665 O(6) O(7) 2.741(7) ? . . O(6) O(7) 3.103(11) ? . 2_875 O(6) O(8) 3.177(8) ? . 1_665 O(6) N(2) 2.836(9) ? . 2_765 O(6) N(4) 3.472(8) ? . 1_665 O(6) C(10) 3.526(6) ? . 1_765 O(7) O(1) 2.851(5) ? . 2_765 O(7) O(2) 3.316(7) ? . 2_765 O(7) O(3) 2.933(9) ? . . O(7) O(5) 3.492(7) ? . 2_766 O(7) O(6) 2.741(7) ? . . O(7) O(6) 3.103(11) ? . 2_875 O(7) N(2) 3.523(9) ? . 2_765 O(7) C(23) 3.148(6) ? . 2_765 O(8) O(2) 2.728(10) ? . . O(8) O(5) 2.831(8) ? . . O(8) O(6) 3.177(8) ? . 1_445 O(8) C(5) 3.457(10) ? . 1_655 O(8) C(6) 3.560(11) ? . 2_656 N(1) O(1) 2.886(7) ? . 2_665 N(1) O(4) 2.895(5) ? . 2_765 N(1) N(3) 3.484(6) ? . 2_665 N(1) C(6) 3.540(5) ? . 1_554 N(2) O(3) 2.730(5) ? . 2_765 N(2) O(4) 3.565(6) ? . 2_765 N(2) O(6) 2.836(9) ? . 2_765 N(2) O(7) 3.523(9) ? . 2_765 N(2) C(24) 3.515(6) ? . 2_765 N(3) O(1) 2.849(5) ? . . N(3) O(2) 3.542(6) ? . . N(3) O(4) 2.790(7) ? . 1_455 N(3) N(1) 3.484(6) ? . 2_665 N(3) C(23) 3.568(6) ? . . N(4) O(2) 2.849(5) ? . . N(4) O(5) 2.986(6) ? . 2_656 N(4) O(6) 3.472(8) ? . 1_445 C(2) C(5) 3.496(6) ? . 2_555 C(2) C(18) 3.475(8) ? . 2_665 C(3) O(5) 3.550(5) ? . 1_454 C(3) C(5) 3.549(7) ? . 2_555 C(3) C(6) 3.598(5) ? . 2_555 C(3) C(18) 3.519(8) ? . 2_665 C(3) C(19) 3.525(8) ? . 2_665 C(4) C(11) 3.433(5) ? . 2_555 C(4) C(12) 3.486(6) ? . 2_555 C(5) O(8) 3.457(10) ? . 1_455 C(5) C(2) 3.496(6) ? . 2_555 C(5) C(3) 3.549(7) ? . 2_555 C(6) O(8) 3.560(11) ? . 2_656 C(6) N(1) 3.540(5) ? . 1_556 C(6) C(3) 3.598(5) ? . 2_555 C(6) C(15) 3.512(5) ? . 1_556 C(7) O(4) 3.430(4) ? . 2_766 C(7) O(5) 3.413(7) ? . 2_656 C(9) O(4) 3.381(4) ? . 1_455 C(9) C(21) 3.548(6) ? . 1_455 C(10) O(6) 3.526(6) ? . 1_345 C(10) C(13) 3.430(5) ? . 2_555 C(10) C(14) 3.459(6) ? . 2_555 C(10) C(21) 3.560(5) ? . 1_455 C(10) C(22) 3.175(6) ? . 1_455 C(11) C(4) 3.433(5) ? . 2_555 C(11) C(21) 3.440(7) ? . 1_455 C(12) C(4) 3.486(6) ? . 2_555 C(12) C(14) 3.573(5) ? . 2_555 C(12) C(21) 3.444(6) ? . 1_455 C(12) C(22) 3.395(7) ? . 1_455 C(13) C(10) 3.430(5) ? . 2_555 C(14) C(10) 3.459(6) ? . 2_555 C(14) C(12) 3.573(5) ? . 2_555 C(14) C(14) 3.594(7) ? . 2_555 C(14) C(22) 3.518(5) ? . 1_455 C(15) C(6) 3.512(5) ? . 1_554 C(18) C(2) 3.475(8) ? . 2_665 C(18) C(3) 3.519(8) ? . 2_665 C(19) C(3) 3.525(8) ? . 2_665 C(21) O(2) 3.468(5) ? . 2_766 C(21) C(9) 3.548(6) ? . 1_655 C(21) C(10) 3.560(5) ? . 1_655 C(21) C(11) 3.440(7) ? . 1_655 C(21) C(12) 3.444(6) ? . 1_655 C(22) O(2) 3.490(4) ? . 2_766 C(22) C(10) 3.175(6) ? . 1_655 C(22) C(12) 3.395(7) ? . 1_655 C(22) C(14) 3.518(5) ? . 1_655 C(22) C(22) 3.551(6) ? . 2_766 C(22) C(23) 3.432(5) ? . 2_766 C(23) O(7) 3.148(6) ? . 2_765 C(23) N(3) 3.568(6) ? . . C(23) C(22) 3.432(5) ? . 2_766 C(24) O(5) 3.589(6) ? . 2_766 C(24) N(2) 3.515(6) ? . 2_765 O(1) H(1) 3.328 ? . 2_665 O(1) H(11) 3.442 ? . 2_766 O(1) H(12) 3.476 ? . 2_766 O(1) H(13) 2.03(7) ? . 2_665 O(1) H(14) 3.09(6) ? . 2_665 O(1) H(17) 1.96(6) ? . . O(1) H(18) 3.39(7) ? . . O(1) H(19) 2.89(6) ? . . O(2) H(8) 3.170 ? . 1_655 O(2) H(11) 3.496 ? . 2_766 O(2) H(12) 3.526 ? . 2_766 O(2) H(17) 2.88(7) ? . . O(2) H(19) 1.86(5) ? . . O(2) H(20) 3.41(5) ? . . O(3) H(6) 2.882 ? . 2_766 O(3) H(14) 3.09(6) ? . 2_765 O(3) H(15) 3.28(5) ? . 2_765 O(3) H(16) 1.76(8) ? . 2_765 O(4) H(6) 2.935 ? . 2_766 O(4) H(7) 3.076 ? . 1_655 O(4) H(13) 3.45(6) ? . 2_765 O(4) H(14) 2.08(5) ? . 2_765 O(4) H(16) 2.81(8) ? . 2_765 O(4) H(17) 3.17(7) ? . 1_655 O(4) H(18) 1.96(8) ? . 1_655 O(5) H(2) 2.659 ? . 1_656 O(5) H(6) 2.999 ? . 2_656 O(5) H(10) 3.451 ? . 2_766 O(5) H(20) 3.32(7) ? . . O(5) H(20) 2.07(7) ? . 2_656 O(6) H(3) 2.771 ? . 1_765 O(6) H(7) 3.251 ? . 2_765 O(6) H(8) 2.647 ? . 1_765 O(6) H(15) 2.12(6) ? . 2_765 O(6) H(16) 3.12(9) ? . 2_765 O(6) H(19) 3.07(6) ? . 1_665 O(6) H(20) 3.35(6) ? . 1_665 O(7) H(3) 2.865 ? . 2_665 O(7) H(10) 3.179 ? . . O(7) H(15) 3.44(5) ? . 2_765 O(7) H(16) 3.13(9) ? . 2_765 O(7) H(17) 3.43(5) ? . 2_765 O(7) H(19) 3.33(6) ? . 2_765 O(7) H(20) 3.49(5) ? . 1_665 O(8) H(1) 3.506 ? . 1_656 O(8) H(2) 3.107 ? . 1_656 O(8) H(4) 2.597 ? . 1_655 O(8) H(5) 3.085 ? . 2_656 O(8) H(6) 3.426 ? . 2_656 O(8) H(8) 3.121 ? . 1_655 O(8) H(12) 3.343 ? . . O(8) H(15) 3.35(4) ? . 2_655 O(8) H(19) 3.11(7) ? . . O(8) H(20) 3.50(7) ? . . N(1) H(5) 3.232 ? . 1_554 N(1) H(6) 3.541 ? . 1_554 N(1) H(17) 3.05(6) ? . 2_665 N(1) H(18) 3.27(6) ? . 2_665 N(2) H(5) 3.039 ? . 1_554 N(2) H(6) 3.254 ? . 1_554 N(3) H(11) 3.089 ? . 2_766 N(3) H(13) 3.28(5) ? . 2_665 N(3) H(14) 2.96(5) ? . 2_665 C(1) H(5) 3.292 ? . 1_554 C(2) H(4) 3.521 ? . 2_555 C(2) H(5) 3.126 ? . 1_554 C(2) H(9) 2.852 ? . 2_665 C(3) H(9) 3.076 ? . 2_665 C(3) H(10) 3.089 ? . 2_665 C(5) H(1) 3.361 ? . 1_556 C(5) H(5) 3.076 ? . 2_556 C(5) H(12) 3.323 ? . 1_455 C(6) H(1) 3.163 ? . 1_556 C(6) H(2) 3.501 ? . 2_555 C(6) H(4) 3.138 ? . 2_556 C(6) H(5) 3.470 ? . 2_556 C(6) H(14) 3.57(3) ? . 1_556 C(7) H(2) 3.478 ? . 2_555 C(7) H(14) 3.43(4) ? . 1_556 C(7) H(16) 3.52(7) ? . 1_556 C(8) H(3) 3.577 ? . 2_555 C(8) H(11) 3.484 ? . 1_455 C(9) H(8) 3.585 ? . 2_555 C(9) H(11) 3.421 ? . 1_455 C(10) H(12) 3.096 ? . 1_455 C(10) H(15) 3.55(4) ? . 2_555 C(11) H(3) 3.382 ? . 2_555 C(11) H(11) 3.069 ? . 1_455 C(12) H(11) 3.249 ? . 1_455 C(12) H(12) 3.163 ? . 1_455 C(13) H(8) 3.379 ? . 2_555 C(15) H(5) 2.892 ? . 1_554 C(16) H(11) 3.596 ? . 2_766 C(17) H(12) 3.125 ? . 2_766 C(18) H(1) 3.189 ? . 2_665 C(18) H(2) 3.284 ? . 2_665 C(18) H(9) 3.216 ? . 2_765 C(18) H(10) 3.288 ? . 2_765 C(19) H(2) 3.039 ? . 2_665 C(19) H(9) 3.055 ? . 2_765 C(21) H(17) 3.45(5) ? . 2_766 C(22) H(8) 3.321 ? . 1_655 C(22) H(12) 3.252 ? . 2_766 C(23) H(11) 3.514 ? . 2_766 C(23) H(12) 3.131 ? . 2_766 C(23) H(13) 3.23(7) ? . 2_665 C(23) H(17) 2.71(6) ? . . C(23) H(19) 2.69(5) ? . . C(24) H(6) 3.055 ? . 2_766 C(24) H(14) 2.89(6) ? . 2_765 C(24) H(16) 2.58(7) ? . 2_765 C(24) H(18) 3.16(8) ? . 1_655 H(1) O(1) 3.328 ? . 2_665 H(1) O(8) 3.506 ? . 1_454 H(1) C(5) 3.361 ? . 1_554 H(1) C(6) 3.163 ? . 1_554 H(1) C(18) 3.189 ? . 2_665 H(1) H(4) 3.061 ? . 1_554 H(1) H(5) 2.705 ? . 1_554 H(1) H(9) 2.700 ? . 2_665 H(2) O(5) 2.659 ? . 1_454 H(2) O(8) 3.107 ? . 1_454 H(2) C(6) 3.501 ? . 2_555 H(2) C(7) 3.478 ? . 2_555 H(2) C(18) 3.284 ? . 2_665 H(2) C(19) 3.039 ? . 2_665 H(2) H(9) 3.096 ? . 2_665 H(2) H(10) 2.645 ? . 2_665 H(2) H(20) 3.568 ? . 2_555 H(3) O(6) 2.771 ? . 1_345 H(3) O(7) 2.865 ? . 2_665 H(3) C(8) 3.577 ? . 2_555 H(3) C(11) 3.382 ? . 2_555 H(4) O(8) 2.597 ? . 1_455 H(4) C(2) 3.521 ? . 2_555 H(4) C(6) 3.138 ? . 2_556 H(4) H(1) 3.061 ? . 1_556 H(4) H(4) 3.427 ? . 2_556 H(4) H(5) 2.375 ? . 2_556 H(4) H(12) 3.283 ? . 1_455 H(4) H(15) 3.481 ? . 2_555 H(5) O(8) 3.085 ? . 2_656 H(5) N(1) 3.232 ? . 1_556 H(5) N(2) 3.039 ? . 1_556 H(5) C(1) 3.292 ? . 1_556 H(5) C(2) 3.126 ? . 1_556 H(5) C(5) 3.076 ? . 2_556 H(5) C(6) 3.470 ? . 2_556 H(5) C(15) 2.892 ? . 1_556 H(5) H(1) 2.705 ? . 1_556 H(5) H(4) 2.375 ? . 2_556 H(5) H(5) 3.160 ? . 2_556 H(5) H(13) 3.556 ? . 1_556 H(5) H(14) 3.423 ? . 1_556 H(5) H(15) 3.222 ? . 1_556 H(5) H(16) 3.327 ? . 1_556 H(6) O(3) 2.882 ? . 2_766 H(6) O(4) 2.935 ? . 2_766 H(6) O(5) 2.999 ? . 2_656 H(6) O(8) 3.426 ? . 2_656 H(6) N(1) 3.541 ? . 1_556 H(6) N(2) 3.254 ? . 1_556 H(6) C(24) 3.055 ? . 2_766 H(6) H(14) 3.173 ? . 1_556 H(6) H(16) 2.816 ? . 1_556 H(7) O(4) 3.076 ? . 1_455 H(7) O(6) 3.251 ? . 2_765 H(8) O(2) 3.170 ? . 1_455 H(8) O(6) 2.647 ? . 1_345 H(8) O(8) 3.121 ? . 1_455 H(8) C(9) 3.585 ? . 2_555 H(8) C(13) 3.379 ? . 2_555 H(8) C(22) 3.321 ? . 1_455 H(8) H(12) 3.084 ? . 1_455 H(8) H(15) 2.803 ? . 2_555 H(9) C(2) 2.852 ? . 2_665 H(9) C(3) 3.076 ? . 2_665 H(9) C(18) 3.216 ? . 2_765 H(9) C(19) 3.055 ? . 2_765 H(9) H(1) 2.700 ? . 2_665 H(9) H(2) 3.096 ? . 2_665 H(9) H(9) 2.897 ? . 2_765 H(9) H(10) 2.589 ? . 2_765 H(9) H(13) 3.024 ? . 2_665 H(10) O(5) 3.451 ? . 2_766 H(10) O(7) 3.179 ? . . H(10) C(3) 3.089 ? . 2_665 H(10) C(18) 3.288 ? . 2_765 H(10) H(2) 2.645 ? . 2_665 H(10) H(9) 2.589 ? . 2_765 H(11) O(1) 3.442 ? . 2_766 H(11) O(2) 3.496 ? . 2_766 H(11) N(3) 3.089 ? . 2_766 H(11) C(8) 3.484 ? . 1_655 H(11) C(9) 3.421 ? . 1_655 H(11) C(11) 3.069 ? . 1_655 H(11) C(12) 3.249 ? . 1_655 H(11) C(16) 3.596 ? . 2_766 H(11) C(23) 3.514 ? . 2_766 H(11) H(17) 2.737 ? . 2_766 H(11) H(18) 3.160 ? . 1_655 H(11) H(18) 3.394 ? . 2_766 H(11) H(19) 3.382 ? . 2_766 H(12) O(1) 3.476 ? . 2_766 H(12) O(2) 3.526 ? . 2_766 H(12) O(8) 3.343 ? . . H(12) C(5) 3.323 ? . 1_655 H(12) C(10) 3.096 ? . 1_655 H(12) C(12) 3.163 ? . 1_655 H(12) C(17) 3.125 ? . 2_766 H(12) C(22) 3.252 ? . 2_766 H(12) C(23) 3.131 ? . 2_766 H(12) H(4) 3.283 ? . 1_655 H(12) H(8) 3.084 ? . 1_655 H(12) H(12) 3.211 ? . 2_766 H(13) O(1) 2.03(7) ? . 2_665 H(13) O(4) 3.45(6) ? . 2_765 H(13) N(3) 3.28(5) ? . 2_665 H(13) C(23) 3.23(7) ? . 2_665 H(13) H(5) 3.556 ? . 1_554 H(13) H(9) 3.024 ? . 2_665 H(13) H(17) 2.65(8) ? . 2_665 H(13) H(18) 3.31(8) ? . 2_665 H(14) O(1) 3.09(6) ? . 2_665 H(14) O(3) 3.09(6) ? . 2_765 H(14) O(4) 2.08(5) ? . 2_765 H(14) N(3) 2.96(5) ? . 2_665 H(14) C(6) 3.57(3) ? . 1_554 H(14) C(7) 3.43(4) ? . 1_554 H(14) C(24) 2.89(6) ? . 2_765 H(14) H(5) 3.423 ? . 1_554 H(14) H(6) 3.173 ? . 1_554 H(14) H(17) 2.71(9) ? . 2_665 H(14) H(18) 2.59(9) ? . 2_665 H(15) O(3) 3.28(5) ? . 2_765 H(15) O(6) 2.12(6) ? . 2_765 H(15) O(7) 3.44(5) ? . 2_765 H(15) O(8) 3.35(4) ? . 2_655 H(15) C(10) 3.55(4) ? . 2_555 H(15) H(4) 3.481 ? . 2_555 H(15) H(5) 3.222 ? . 1_554 H(15) H(8) 2.803 ? . 2_555 H(16) O(3) 1.76(8) ? . 2_765 H(16) O(4) 2.81(8) ? . 2_765 H(16) O(6) 3.12(9) ? . 2_765 H(16) O(7) 3.13(9) ? . 2_765 H(16) C(7) 3.52(7) ? . 1_554 H(16) C(24) 2.58(7) ? . 2_765 H(16) H(5) 3.327 ? . 1_554 H(16) H(6) 2.816 ? . 1_554 H(17) O(1) 1.96(6) ? . . H(17) O(2) 2.88(7) ? . . H(17) O(4) 3.17(7) ? . 1_455 H(17) O(7) 3.43(5) ? . 2_765 H(17) N(1) 3.05(6) ? . 2_665 H(17) C(21) 3.45(5) ? . 2_766 H(17) C(23) 2.71(6) ? . . H(17) H(11) 2.737 ? . 2_766 H(17) H(13) 2.65(8) ? . 2_665 H(17) H(14) 2.71(9) ? . 2_665 H(18) O(1) 3.39(7) ? . . H(18) O(4) 1.96(8) ? . 1_455 H(18) N(1) 3.27(6) ? . 2_665 H(18) C(24) 3.16(8) ? . 1_455 H(18) H(11) 3.160 ? . 1_455 H(18) H(11) 3.394 ? . 2_766 H(18) H(13) 3.31(8) ? . 2_665 H(18) H(14) 2.59(9) ? . 2_665 H(18) H(18) 3.53(8) ? . 2_666 H(19) O(1) 2.89(6) ? . . H(19) O(2) 1.86(5) ? . . H(19) O(6) 3.07(6) ? . 1_445 H(19) O(7) 3.33(5) ? . 2_765 H(19) O(8) 3.11(7) ? . . H(19) C(23) 2.69(5) ? . . H(19) H(11) 3.382 ? . 2_766 H(20) O(2) 3.41(5) ? . . H(20) O(5) 3.32(7) ? . . H(20) O(5) 2.07(7) ? . 2_656 H(20) O(6) 3.35(6) ? . 1_445 H(20) O(7) 3.49(5) ? . 1_445 H(20) O(8) 3.50(7) ? . . H(20) H(2) 3.568 ? . 2_555 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__kusu065 _database_code_depnum_ccdc_archive 'CCDC 920482' #TrackingRef '16985_web_deposit_cif_file_0_TakahiroKusukawa_1358506685.1c2_2b2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H20 F4 N4 O6 ' _chemical_formula_moiety 'C24 H20 F4 N4 O6 ' _chemical_formula_weight 536.44 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.480(5) _cell_length_b 11.934(5) _cell_length_c 10.976(4) _cell_angle_alpha 109.92(3) _cell_angle_beta 102.60(3) _cell_angle_gamma 111.76(3) _cell_volume 1206.6(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 18 _cell_measurement_theta_min 25.0 _cell_measurement_theta_max 30.0 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552.00 _exptl_absorpt_coefficient_mu 1.109 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 0.895 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 5843 _diffrn_reflns_av_R_equivalents 0.070 _diffrn_reflns_theta_max 66.80 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 66.80 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -5.85 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4266 _reflns_number_gt 2801 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1920 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4266 _refine_ls_number_parameters 366 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0964P)^2^+0.7657P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.74 _refine_diff_density_min -0.33 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.073 0.053 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 F(1) F 1.0800(2) -0.2635(2) 0.2679(2) 0.0419(5) Uani 1.00 1 d . . . F(2) F 0.9333(2) -0.1514(2) 0.3572(2) 0.0403(5) Uani 1.00 1 d . . . F(3) F 0.8237(2) -0.0973(2) -0.0509(2) 0.0477(5) Uani 1.00 1 d . . . F(4) F 0.9708(2) -0.2104(2) -0.1423(2) 0.0501(5) Uani 1.00 1 d . . . O(1) O 1.0502(2) -0.4119(2) -0.1120(2) 0.0475(6) Uani 1.00 1 d . . . O(2) O 1.2329(2) -0.2521(2) 0.0832(2) 0.0491(7) Uani 1.00 1 d . . . O(3) O 0.6625(2) -0.1395(2) 0.1484(2) 0.0477(6) Uani 1.00 1 d . . . O(4) O 0.8454(2) 0.0571(2) 0.3028(2) 0.0442(6) Uani 1.00 1 d . . . O(5) O 0.1111(2) -0.4568(2) 0.3976(2) 0.0399(5) Uiso 1.00 1 d . . . O(6) O 0.9718(2) 0.6664(2) 0.5249(2) 0.0408(5) Uiso 1.00 1 d . . . N(1) N 0.4981(3) -0.0443(3) 0.2470(3) 0.0404(7) Uani 1.00 1 d . . . N(2) N 0.6775(2) 0.1678(2) 0.3962(3) 0.0348(6) Uani 1.00 1 d . . . N(3) N 0.6071(3) 0.3277(3) 0.0469(3) 0.0410(7) Uani 1.00 1 d . . . N(4) N 0.7921(3) 0.5199(3) 0.2250(3) 0.0413(7) Uani 1.00 1 d . . . C(1) C 0.4465(3) 0.1238(3) 0.3766(3) 0.0303(6) Uani 1.00 1 d . . . C(2) C 0.3627(3) 0.0512(3) 0.4243(3) 0.0334(7) Uani 1.00 1 d . . . C(3) C 0.2646(3) 0.0841(3) 0.4618(3) 0.0342(7) Uani 1.00 1 d . . . C(4) C 0.2517(3) 0.1871(3) 0.4469(3) 0.0351(7) Uani 1.00 1 d . . . C(5) C 0.3750(3) 0.5440(3) 0.2957(3) 0.0362(7) Uani 1.00 1 d . . . C(6) C 0.4516(4) 0.6151(3) 0.2439(3) 0.0413(8) Uani 1.00 1 d . . . C(7) C 0.5513(3) 0.5841(3) 0.2048(3) 0.0378(7) Uani 1.00 1 d . . . C(8) C 0.5671(3) 0.4805(3) 0.2180(3) 0.0293(6) Uani 1.00 1 d . . . C(9) C 0.5092(3) 0.3028(3) 0.2983(3) 0.0297(6) Uani 1.00 1 d . . . C(10) C 0.3169(3) 0.3673(3) 0.3741(3) 0.0327(7) Uani 1.00 1 d . . . C(11) C 0.4908(3) 0.4056(3) 0.2766(3) 0.0283(6) Uani 1.00 1 d . . . C(12) C 0.3919(3) 0.4387(3) 0.3164(3) 0.0305(6) Uani 1.00 1 d . . . C(13) C 0.4345(3) 0.2329(3) 0.3574(3) 0.0285(6) Uani 1.00 1 d . . . C(14) C 0.3327(3) 0.2639(3) 0.3937(3) 0.0300(6) Uani 1.00 1 d . . . C(15) C 0.5451(3) 0.0817(3) 0.3378(3) 0.0302(6) Uani 1.00 1 d . . . C(16) C 0.6604(3) 0.4412(3) 0.1619(3) 0.0283(6) Uani 1.00 1 d . . . C(17) C 1.0278(3) -0.2435(3) 0.0579(3) 0.0311(6) Uani 1.00 1 d . . . C(18) C 1.0169(3) -0.2238(3) 0.1860(3) 0.0302(6) Uani 1.00 1 d . . . C(19) C 0.9424(3) -0.1647(3) 0.2331(3) 0.0300(6) Uani 1.00 1 d . . . C(20) C 0.8747(3) -0.1207(3) 0.1560(3) 0.0303(7) Uani 1.00 1 d . . . C(21) C 0.8855(3) -0.1393(3) 0.0286(3) 0.0346(7) Uani 1.00 1 d . . . C(22) C 0.9598(3) -0.1994(3) -0.0196(3) 0.0349(7) Uani 1.00 1 d . . . C(23) C 1.1104(3) -0.3086(3) 0.0045(3) 0.0358(7) Uani 1.00 1 d . . . C(24) C 0.7874(3) -0.0607(3) 0.2063(3) 0.0302(6) Uani 1.00 1 d . . . H(1) H 0.3702 -0.0220 0.4325 0.040 Uiso 1.00 1 c R . . H(2) H 0.2090 0.0346 0.4966 0.041 Uiso 1.00 1 c R . . H(3) H 0.1870 0.2087 0.4726 0.042 Uiso 1.00 1 c R . . H(4) H 0.3086 0.5644 0.3188 0.043 Uiso 1.00 1 c R . . H(5) H 0.4397 0.6855 0.2334 0.050 Uiso 1.00 1 c R . . H(6) H 0.6056 0.6350 0.1701 0.045 Uiso 1.00 1 c R . . H(7) H 0.5736 0.2807 0.2722 0.036 Uiso 1.00 1 c R . . H(8) H 0.2530 0.3898 0.4009 0.039 Uiso 1.00 1 c R . . H(9) H 0.403(4) -0.099(4) 0.206(4) 0.048(11) Uiso 1.00 1 c . . . H(10) H 0.557(4) -0.075(4) 0.221(4) 0.054(11) Uiso 1.00 1 c . . . H(11) H 0.717(4) 0.262(4) 0.471(4) 0.063(13) Uiso 1.00 1 c . . . H(12) H 0.738(4) 0.137(4) 0.370(4) 0.062(13) Uiso 1.00 1 c . . . H(13) H 0.664(4) 0.301(4) 0.011(4) 0.059(12) Uiso 1.00 1 c . . . H(14) H 0.512(5) 0.277(5) -0.006(5) 0.081(16) Uiso 1.00 1 c . . . H(15) H 0.854(4) 0.494(4) 0.198(4) 0.058(12) Uiso 1.00 1 c . . . H(16) H 0.827(5) 0.601(5) 0.319(5) 0.083(15) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0474(12) 0.0523(12) 0.0426(11) 0.0360(10) 0.0202(9) 0.0248(9) F(2) 0.0492(12) 0.0539(12) 0.0338(10) 0.0335(10) 0.0253(9) 0.0223(9) F(3) 0.0531(13) 0.0669(14) 0.0349(10) 0.0413(11) 0.0158(9) 0.0237(10) F(4) 0.0519(13) 0.0782(15) 0.0280(10) 0.0401(12) 0.0210(9) 0.0200(10) O(1) 0.0339(13) 0.0482(14) 0.0348(13) 0.0202(12) 0.0080(10) -0.0042(11) O(2) 0.0274(12) 0.0523(15) 0.0437(14) 0.0200(12) 0.0104(11) -0.0012(11) O(3) 0.0267(12) 0.0415(14) 0.0500(14) 0.0174(11) 0.0093(11) -0.0021(11) O(4) 0.0346(13) 0.0337(13) 0.0483(14) 0.0174(11) 0.0155(11) 0.0019(11) N(1) 0.0289(15) 0.0334(15) 0.0436(16) 0.0180(13) 0.0102(13) 0.0012(13) N(2) 0.0269(14) 0.0316(14) 0.0391(15) 0.0169(12) 0.0110(12) 0.0078(12) N(3) 0.0286(15) 0.0442(17) 0.0326(15) 0.0186(14) 0.0111(12) -0.0009(13) N(4) 0.0278(15) 0.0395(16) 0.0381(15) 0.0172(13) 0.0091(12) 0.0002(13) C(1) 0.0296(16) 0.0325(16) 0.0233(14) 0.0176(14) 0.0079(12) 0.0061(12) C(2) 0.0353(18) 0.0332(16) 0.0317(16) 0.0184(15) 0.0128(14) 0.0136(13) C(3) 0.0316(17) 0.0367(17) 0.0321(16) 0.0154(15) 0.0152(14) 0.0134(14) C(4) 0.0321(17) 0.0431(19) 0.0283(16) 0.0217(15) 0.0125(13) 0.0104(14) C(5) 0.0422(19) 0.0414(18) 0.0344(16) 0.0316(16) 0.0177(15) 0.0135(14) C(6) 0.053(2) 0.045(2) 0.0450(19) 0.0371(19) 0.0241(17) 0.0239(17) C(7) 0.044(2) 0.0364(18) 0.0389(18) 0.0231(16) 0.0209(16) 0.0171(15) C(8) 0.0326(17) 0.0285(15) 0.0227(14) 0.0172(13) 0.0085(12) 0.0065(12) C(9) 0.0300(16) 0.0324(16) 0.0281(15) 0.0206(14) 0.0115(13) 0.0094(12) C(10) 0.0314(16) 0.0422(18) 0.0281(15) 0.0253(15) 0.0128(13) 0.0111(13) C(11) 0.0284(16) 0.0308(15) 0.0231(14) 0.0181(14) 0.0075(12) 0.0073(12) C(12) 0.0302(16) 0.0352(16) 0.0246(14) 0.0198(14) 0.0087(12) 0.0094(13) C(13) 0.0276(16) 0.0326(16) 0.0240(14) 0.0177(14) 0.0103(12) 0.0084(12) C(14) 0.0292(16) 0.0354(16) 0.0254(14) 0.0187(14) 0.0109(12) 0.0107(13) C(15) 0.0301(16) 0.0331(16) 0.0279(15) 0.0184(14) 0.0101(13) 0.0123(13) C(16) 0.0287(16) 0.0276(15) 0.0267(14) 0.0140(13) 0.0102(12) 0.0107(12) C(17) 0.0237(15) 0.0336(16) 0.0282(15) 0.0145(14) 0.0099(12) 0.0061(13) C(18) 0.0231(15) 0.0333(16) 0.0314(15) 0.0157(13) 0.0084(12) 0.0113(13) C(19) 0.0318(16) 0.0325(16) 0.0247(14) 0.0169(14) 0.0137(13) 0.0092(12) C(20) 0.0262(16) 0.0298(16) 0.0283(15) 0.0143(14) 0.0092(13) 0.0068(13) C(21) 0.0303(17) 0.0417(18) 0.0302(16) 0.0200(15) 0.0100(13) 0.0135(14) C(22) 0.0324(17) 0.0454(19) 0.0223(15) 0.0205(16) 0.0118(13) 0.0083(14) C(23) 0.0284(17) 0.0388(18) 0.0298(16) 0.0164(15) 0.0116(13) 0.0049(14) C(24) 0.0277(16) 0.0306(16) 0.0289(15) 0.0157(14) 0.0114(13) 0.0085(13) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F(1) C(18) 1.347(5) yes . . F(2) C(19) 1.349(4) yes . . F(3) C(21) 1.345(5) yes . . F(4) C(22) 1.347(4) yes . . O(1) C(23) 1.242(3) yes . . O(2) C(23) 1.244(3) yes . . O(3) C(24) 1.241(3) yes . . O(4) C(24) 1.235(3) yes . . N(1) C(15) 1.300(4) yes . . N(2) C(15) 1.320(3) yes . . N(3) C(16) 1.299(3) yes . . N(4) C(16) 1.302(3) yes . . C(1) C(2) 1.364(5) yes . . C(1) C(13) 1.438(6) yes . . C(1) C(15) 1.483(5) yes . . C(2) C(3) 1.419(6) yes . . C(3) C(4) 1.349(6) yes . . C(4) C(14) 1.420(5) yes . . C(5) C(6) 1.345(6) yes . . C(5) C(12) 1.424(6) yes . . C(6) C(7) 1.432(6) yes . . C(7) C(8) 1.363(6) yes . . C(8) C(11) 1.427(5) yes . . C(8) C(16) 1.486(5) yes . . C(9) C(11) 1.406(6) yes . . C(9) C(13) 1.391(5) yes . . C(10) C(12) 1.389(5) yes . . C(10) C(14) 1.389(6) yes . . C(11) C(12) 1.437(5) yes . . C(13) C(14) 1.444(5) yes . . C(17) C(18) 1.386(5) yes . . C(17) C(22) 1.388(6) yes . . C(17) C(23) 1.525(6) yes . . C(18) C(19) 1.374(5) yes . . C(19) C(20) 1.383(6) yes . . C(20) C(21) 1.380(5) yes . . C(20) C(24) 1.525(5) yes . . C(21) C(22) 1.384(6) yes . . N(1) H(9) 0.94(4) no . . N(1) H(10) 0.93(5) no . . N(2) H(11) 0.98(4) no . . N(2) H(12) 0.96(6) no . . N(3) H(13) 0.93(5) no . . N(3) H(14) 0.94(5) no . . N(4) H(15) 0.94(5) no . . N(4) H(16) 1.01(5) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.940 no . . C(10) H(8) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(13) 120.9(3) yes . . . C(2) C(1) C(15) 117.9(3) yes . . . C(13) C(1) C(15) 121.1(3) yes . . . C(1) C(2) C(3) 121.2(4) yes . . . C(2) C(3) C(4) 119.4(3) yes . . . C(3) C(4) C(14) 122.3(4) yes . . . C(6) C(5) C(12) 121.6(4) yes . . . C(5) C(6) C(7) 120.4(4) yes . . . C(6) C(7) C(8) 119.8(3) yes . . . C(7) C(8) C(11) 121.4(3) yes . . . C(7) C(8) C(16) 118.4(3) yes . . . C(11) C(8) C(16) 120.1(3) yes . . . C(11) C(9) C(13) 121.6(3) yes . . . C(12) C(10) C(14) 122.5(3) yes . . . C(8) C(11) C(9) 123.0(3) yes . . . C(8) C(11) C(12) 118.1(3) yes . . . C(9) C(11) C(12) 118.9(3) yes . . . C(5) C(12) C(10) 122.4(3) yes . . . C(5) C(12) C(11) 118.6(3) yes . . . C(10) C(12) C(11) 118.9(3) yes . . . C(1) C(13) C(9) 123.4(3) yes . . . C(1) C(13) C(14) 117.3(3) yes . . . C(9) C(13) C(14) 119.2(3) yes . . . C(4) C(14) C(10) 122.4(3) yes . . . C(4) C(14) C(13) 118.9(3) yes . . . C(10) C(14) C(13) 118.7(3) yes . . . N(1) C(15) N(2) 120.4(3) yes . . . N(1) C(15) C(1) 118.0(2) yes . . . N(2) C(15) C(1) 121.5(2) yes . . . N(3) C(16) N(4) 120.9(3) yes . . . N(3) C(16) C(8) 118.3(2) yes . . . N(4) C(16) C(8) 120.8(2) yes . . . C(18) C(17) C(22) 116.2(3) yes . . . C(18) C(17) C(23) 122.4(3) yes . . . C(22) C(17) C(23) 121.4(3) yes . . . F(1) C(18) C(17) 120.0(3) yes . . . F(1) C(18) C(19) 118.2(3) yes . . . C(17) C(18) C(19) 121.8(3) yes . . . F(2) C(19) C(18) 118.8(3) yes . . . F(2) C(19) C(20) 119.1(3) yes . . . C(18) C(19) C(20) 122.1(3) yes . . . C(19) C(20) C(21) 116.6(3) yes . . . C(19) C(20) C(24) 121.6(3) yes . . . C(21) C(20) C(24) 121.8(3) yes . . . F(3) C(21) C(20) 119.7(3) yes . . . F(3) C(21) C(22) 118.7(3) yes . . . C(20) C(21) C(22) 121.6(4) yes . . . F(4) C(22) C(17) 119.3(3) yes . . . F(4) C(22) C(21) 118.9(3) yes . . . C(17) C(22) C(21) 121.8(3) yes . . . O(1) C(23) O(2) 126.3(4) yes . . . O(1) C(23) C(17) 117.6(3) yes . . . O(2) C(23) C(17) 116.1(2) yes . . . O(3) C(24) O(4) 126.1(3) yes . . . O(3) C(24) C(20) 115.3(2) yes . . . O(4) C(24) C(20) 118.5(2) yes . . . C(15) N(1) H(9) 116(3) no . . . C(15) N(1) H(10) 120(2) no . . . H(9) N(1) H(10) 124(3) no . . . C(15) N(2) H(11) 122(3) no . . . C(15) N(2) H(12) 119(2) no . . . H(11) N(2) H(12) 118(3) no . . . C(16) N(3) H(13) 119(2) no . . . C(16) N(3) H(14) 121(4) no . . . H(13) N(3) H(14) 119(4) no . . . C(16) N(4) H(15) 123.0(19) no . . . C(16) N(4) H(16) 117(3) no . . . H(15) N(4) H(16) 119(4) no . . . C(1) C(2) H(1) 119.4 no . . . C(3) C(2) H(1) 119.4 no . . . C(2) C(3) H(2) 120.3 no . . . C(4) C(3) H(2) 120.3 no . . . C(3) C(4) H(3) 118.9 no . . . C(14) C(4) H(3) 118.9 no . . . C(6) C(5) H(4) 119.2 no . . . C(12) C(5) H(4) 119.2 no . . . C(5) C(6) H(5) 119.8 no . . . C(7) C(6) H(5) 119.8 no . . . C(6) C(7) H(6) 120.1 no . . . C(8) C(7) H(6) 120.1 no . . . C(11) C(9) H(7) 119.2 no . . . C(13) C(9) H(7) 119.2 no . . . C(12) C(10) H(8) 118.7 no . . . C(14) C(10) H(8) 118.7 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(13) C(9) -174.5(2) ? . . . . C(2) C(1) C(13) C(14) 1.3(3) ? . . . . C(13) C(1) C(2) C(3) -2.4(3) ? . . . . C(2) C(1) C(15) N(1) 54.3(4) ? . . . . C(2) C(1) C(15) N(2) -123.7(3) ? . . . . C(15) C(1) C(2) C(3) -179.2(2) ? . . . . C(13) C(1) C(15) N(1) -122.5(3) ? . . . . C(13) C(1) C(15) N(2) 59.5(4) ? . . . . C(15) C(1) C(13) C(9) 2.2(3) ? . . . . C(15) C(1) C(13) C(14) 178.0(2) ? . . . . C(1) C(2) C(3) C(4) 1.5(3) ? . . . . C(2) C(3) C(4) C(14) 0.5(3) ? . . . . C(3) C(4) C(14) C(10) 178.0(2) ? . . . . C(3) C(4) C(14) C(13) -1.5(3) ? . . . . C(6) C(5) C(12) C(10) 177.8(2) ? . . . . C(6) C(5) C(12) C(11) -1.9(3) ? . . . . C(12) C(5) C(6) C(7) 1.5(4) ? . . . . C(5) C(6) C(7) C(8) 1.0(4) ? . . . . C(6) C(7) C(8) C(11) -3.0(3) ? . . . . C(6) C(7) C(8) C(16) 173.4(2) ? . . . . C(7) C(8) C(11) C(9) -176.8(2) ? . . . . C(7) C(8) C(11) C(12) 2.5(3) ? . . . . C(7) C(8) C(16) N(3) -106.8(3) ? . . . . C(7) C(8) C(16) N(4) 71.8(4) ? . . . . C(11) C(8) C(16) N(3) 69.7(4) ? . . . . C(11) C(8) C(16) N(4) -111.7(3) ? . . . . C(16) C(8) C(11) C(9) 6.8(3) ? . . . . C(16) C(8) C(11) C(12) -173.9(2) ? . . . . C(11) C(9) C(13) C(1) 177.6(2) ? . . . . C(11) C(9) C(13) C(14) 1.9(3) ? . . . . C(13) C(9) C(11) C(8) 179.1(2) ? . . . . C(13) C(9) C(11) C(12) -0.2(3) ? . . . . C(12) C(10) C(14) C(4) -177.2(2) ? . . . . C(12) C(10) C(14) C(13) 2.3(3) ? . . . . C(14) C(10) C(12) C(5) 179.6(2) ? . . . . C(14) C(10) C(12) C(11) -0.6(3) ? . . . . C(8) C(11) C(12) C(5) -0.0(2) ? . . . . C(8) C(11) C(12) C(10) -179.8(2) ? . . . . C(9) C(11) C(12) C(5) 179.3(2) ? . . . . C(9) C(11) C(12) C(10) -0.5(3) ? . . . . C(1) C(13) C(14) C(4) 0.6(3) ? . . . . C(1) C(13) C(14) C(10) -178.9(2) ? . . . . C(9) C(13) C(14) C(4) 176.6(2) ? . . . . C(9) C(13) C(14) C(10) -2.9(3) ? . . . . C(18) C(17) C(22) F(4) 177.3(2) ? . . . . C(18) C(17) C(22) C(21) 0.0(3) ? . . . . C(22) C(17) C(18) F(1) -179.9(2) ? . . . . C(22) C(17) C(18) C(19) 0.4(4) ? . . . . C(18) C(17) C(23) O(1) 123.0(3) ? . . . . C(18) C(17) C(23) O(2) -56.9(4) ? . . . . C(23) C(17) C(18) F(1) -0.5(4) ? . . . . C(23) C(17) C(18) C(19) 179.8(2) ? . . . . C(22) C(17) C(23) O(1) -57.6(5) ? . . . . C(22) C(17) C(23) O(2) 122.5(3) ? . . . . C(23) C(17) C(22) F(4) -2.2(4) ? . . . . C(23) C(17) C(22) C(21) -179.5(2) ? . . . . F(1) C(18) C(19) F(2) -1.3(3) ? . . . . F(1) C(18) C(19) C(20) 179.9(2) ? . . . . C(17) C(18) C(19) F(2) 178.5(2) ? . . . . C(17) C(18) C(19) C(20) -0.4(4) ? . . . . F(2) C(19) C(20) C(21) -178.8(2) ? . . . . F(2) C(19) C(20) C(24) -1.5(3) ? . . . . C(18) C(19) C(20) C(21) 0.0(3) ? . . . . C(18) C(19) C(20) C(24) 177.4(2) ? . . . . C(19) C(20) C(21) F(3) -179.1(2) ? . . . . C(19) C(20) C(21) C(22) 0.3(4) ? . . . . C(19) C(20) C(24) O(3) -101.0(3) ? . . . . C(19) C(20) C(24) O(4) 76.1(4) ? . . . . C(21) C(20) C(24) O(3) 76.2(4) ? . . . . C(21) C(20) C(24) O(4) -106.7(3) ? . . . . C(24) C(20) C(21) F(3) 3.5(4) ? . . . . C(24) C(20) C(21) C(22) -177.0(2) ? . . . . F(3) C(21) C(22) F(4) 1.8(4) ? . . . . F(3) C(21) C(22) C(17) 179.1(2) ? . . . . C(20) C(21) C(22) F(4) -177.6(2) ? . . . . C(20) C(21) C(22) C(17) -0.4(4) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F(1) O(1) 3.200(3) ? . 2_745 F(1) O(5) 3.179(4) ? . 1_655 F(1) O(6) 3.545(4) ? . 1_545 F(1) N(2) 3.598(3) ? . 2_756 F(1) N(4) 3.159(3) ? . 1_545 F(1) C(2) 3.425(3) ? . 1_655 F(1) C(3) 3.425(3) ? . 1_655 F(2) F(2) 3.363(2) ? . 2_756 F(2) O(4) 3.540(3) ? . 2_756 F(2) O(6) 3.377(4) ? . 1_545 F(2) N(4) 3.241(3) ? . 1_545 F(2) C(3) 3.414(3) ? . 1_655 F(2) C(3) 3.462(5) ? . 2_656 F(2) C(4) 3.357(4) ? . 2_656 F(3) F(3) 3.509(3) ? . 2_755 F(3) F(4) 3.104(2) ? . 2_755 F(3) C(9) 3.461(3) ? . 2_655 F(3) C(10) 3.381(3) ? . 2_655 F(3) C(11) 3.571(2) ? . 2_655 F(3) C(12) 3.536(3) ? . 2_655 F(3) C(13) 3.333(3) ? . 2_655 F(3) C(14) 3.262(3) ? . 2_655 F(3) C(21) 3.370(4) ? . 2_755 F(3) C(22) 3.175(4) ? . 2_755 F(4) F(3) 3.104(2) ? . 2_755 F(4) O(4) 3.443(4) ? . 2_755 F(4) O(6) 3.446(3) ? . 1_544 F(4) C(10) 3.064(3) ? . 2_655 F(4) C(21) 3.484(4) ? . 2_755 O(1) F(1) 3.200(3) ? . 2_745 O(1) O(5) 2.771(3) ? . 2_645 O(1) N(3) 3.515(4) ? . 2_755 O(1) N(4) 2.845(5) ? . 2_755 O(2) N(1) 2.762(3) ? . 1_655 O(2) N(3) 2.779(5) ? . 2_755 O(3) N(1) 2.769(5) ? . . O(3) N(3) 2.809(3) ? . 2_655 O(3) C(7) 3.393(5) ? . 1_545 O(4) F(2) 3.540(3) ? . 2_756 O(4) F(4) 3.443(4) ? . 2_755 O(4) O(6) 2.784(2) ? . 2_766 O(4) N(1) 3.549(4) ? . . O(4) N(2) 2.888(5) ? . . O(5) F(1) 3.179(4) ? . 1_455 O(5) O(1) 2.771(3) ? . 2_645 O(5) O(6) 2.826(4) ? . 1_445 O(5) O(6) 2.815(4) ? . 2_656 O(5) N(2) 2.999(2) ? . 2_656 O(5) N(4) 3.596(4) ? . 1_445 O(5) C(5) 3.449(5) ? . 1_545 O(6) F(1) 3.545(4) ? . 1_565 O(6) F(2) 3.377(4) ? . 1_565 O(6) F(4) 3.446(3) ? . 1_566 O(6) O(4) 2.784(2) ? . 2_766 O(6) O(5) 2.826(4) ? . 1_665 O(6) O(5) 2.815(4) ? . 2_656 O(6) N(2) 3.504(3) ? . 2_766 O(6) N(4) 2.931(3) ? . . N(1) O(2) 2.762(3) ? . 1_455 N(1) O(3) 2.769(5) ? . . N(1) O(4) 3.549(4) ? . . N(1) N(3) 3.337(4) ? . 2_655 N(1) C(24) 3.513(5) ? . . N(2) F(1) 3.598(3) ? . 2_756 N(2) O(4) 2.888(5) ? . . N(2) O(5) 2.999(2) ? . 2_656 N(2) O(6) 3.504(3) ? . 2_766 N(3) O(1) 3.515(4) ? . 2_755 N(3) O(2) 2.779(5) ? . 2_755 N(3) O(3) 2.809(3) ? . 2_655 N(3) N(1) 3.337(4) ? . 2_655 N(3) C(6) 3.463(6) ? . 2_665 N(3) C(23) 3.485(5) ? . 2_755 N(4) F(1) 3.159(3) ? . 1_565 N(4) F(2) 3.241(3) ? . 1_565 N(4) O(1) 2.845(5) ? . 2_755 N(4) O(5) 3.596(4) ? . 1_665 N(4) O(6) 2.931(3) ? . . N(4) C(18) 3.424(5) ? . 1_565 N(4) C(19) 3.471(5) ? . 1_565 N(4) C(23) 3.599(5) ? . 2_755 C(2) F(1) 3.425(3) ? . 1_455 C(3) F(1) 3.425(3) ? . 1_455 C(3) F(2) 3.414(3) ? . 1_455 C(3) F(2) 3.462(5) ? . 2_656 C(3) C(6) 3.574(3) ? . 2_666 C(3) C(18) 3.416(3) ? . 1_455 C(3) C(19) 3.395(3) ? . 1_455 C(4) F(2) 3.357(4) ? . 2_656 C(4) C(6) 3.496(4) ? . 2_666 C(4) C(7) 3.424(3) ? . 2_666 C(5) O(5) 3.449(5) ? . 1_565 C(5) C(13) 3.392(3) ? . 2_666 C(5) C(14) 3.481(3) ? . 2_666 C(6) N(3) 3.463(6) ? . 2_665 C(6) C(3) 3.574(3) ? . 2_666 C(6) C(4) 3.496(4) ? . 2_666 C(7) O(3) 3.393(5) ? . 1_565 C(7) C(4) 3.424(3) ? . 2_666 C(9) F(3) 3.461(3) ? . 2_655 C(10) F(3) 3.381(3) ? . 2_655 C(10) F(4) 3.064(3) ? . 2_655 C(10) C(11) 3.422(3) ? . 2_666 C(10) C(12) 3.467(3) ? . 2_666 C(11) F(3) 3.571(2) ? . 2_655 C(11) C(10) 3.422(3) ? . 2_666 C(12) F(3) 3.536(3) ? . 2_655 C(12) C(10) 3.467(3) ? . 2_666 C(12) C(14) 3.509(3) ? . 2_666 C(13) F(3) 3.333(3) ? . 2_655 C(13) C(5) 3.392(3) ? . 2_666 C(14) F(3) 3.262(3) ? . 2_655 C(14) C(5) 3.481(3) ? . 2_666 C(14) C(12) 3.509(3) ? . 2_666 C(18) N(4) 3.424(5) ? . 1_545 C(18) C(3) 3.416(3) ? . 1_655 C(19) N(4) 3.471(5) ? . 1_545 C(19) C(3) 3.395(3) ? . 1_655 C(21) F(3) 3.370(4) ? . 2_755 C(21) F(4) 3.484(4) ? . 2_755 C(22) F(3) 3.175(4) ? . 2_755 C(23) N(3) 3.485(5) ? . 2_755 C(23) N(4) 3.599(5) ? . 2_755 C(24) N(1) 3.513(5) ? . . F(1) H(1) 3.062 ? . 1_655 F(1) H(2) 3.089 ? . 1_655 F(1) H(11) 3.27(5) ? . 2_756 F(1) H(12) 3.52(4) ? . 2_756 F(1) H(15) 2.78(4) ? . 1_545 F(1) H(16) 3.04(6) ? . 1_545 F(2) H(2) 2.766 ? . 1_655 F(2) H(2) 2.914 ? . 2_656 F(2) H(3) 2.676 ? . 2_656 F(2) H(6) 3.290 ? . 1_545 F(2) H(16) 2.58(6) ? . 1_545 F(4) H(8) 2.800 ? . 2_655 O(1) H(13) 2.82(4) ? . 2_755 O(1) H(15) 1.92(5) ? . 2_755 O(1) H(16) 3.54(6) ? . 2_755 O(2) H(1) 3.421 ? . 1_655 O(2) H(5) 3.057 ? . 1_645 O(2) H(9) 1.87(3) ? . 1_655 O(2) H(10) 3.19(4) ? . 1_655 O(2) H(13) 1.85(5) ? . 2_755 O(2) H(14) 3.31(7) ? . 2_755 O(2) H(15) 3.05(4) ? . 2_755 O(3) H(2) 3.424 ? . 2_656 O(3) H(5) 3.191 ? . 1_545 O(3) H(6) 2.632 ? . 1_545 O(3) H(9) 3.35(5) ? . . O(3) H(10) 1.84(5) ? . . O(3) H(12) 3.00(4) ? . . O(3) H(13) 3.21(4) ? . 2_655 O(3) H(14) 1.90(4) ? . 2_655 O(4) H(2) 2.859 ? . 2_656 O(4) H(3) 3.373 ? . 1_655 O(4) H(10) 2.85(4) ? . . O(4) H(11) 3.51(6) ? . . O(4) H(12) 1.93(6) ? . . O(5) H(4) 2.556 ? . 1_545 O(5) H(8) 2.871 ? . 1_545 O(5) H(11) 2.11(3) ? . 2_656 O(5) H(12) 3.26(4) ? . 2_656 O(5) H(15) 2.98(5) ? . 1_445 O(5) H(16) 3.56(7) ? . 1_445 O(6) H(3) 2.748 ? . 2_666 O(6) H(8) 2.790 ? . 2_666 O(6) H(11) 3.33(5) ? . 2_766 O(6) H(12) 2.93(4) ? . 2_766 O(6) H(15) 3.12(4) ? . . O(6) H(16) 2.16(5) ? . . N(1) H(1) 3.191 ? . 2_656 N(1) H(5) 2.982 ? . 1_545 N(1) H(13) 2.90(3) ? . 2_655 N(1) H(14) 3.06(6) ? . 2_655 N(2) H(1) 2.972 ? . 2_656 N(2) H(2) 3.538 ? . 2_656 N(2) H(4) 3.552 ? . 2_666 N(3) H(5) 2.943 ? . 2_665 N(3) H(6) 3.290 ? . 2_665 N(3) H(9) 3.11(4) ? . 2_655 N(3) H(10) 2.94(3) ? . 2_655 C(1) H(1) 3.464 ? . 2_656 C(1) H(4) 3.549 ? . 2_666 C(2) H(1) 3.325 ? . 2_656 C(2) H(5) 3.477 ? . 2_666 C(3) H(5) 3.484 ? . 2_666 C(4) H(16) 3.48(6) ? . 2_666 C(5) H(11) 3.47(5) ? . 2_666 C(6) H(10) 3.56(5) ? . 1_565 C(6) H(13) 3.44(5) ? . 2_665 C(6) H(14) 3.32(7) ? . 2_665 C(7) H(3) 3.400 ? . 2_666 C(7) H(6) 3.599 ? . 2_665 C(7) H(14) 3.27(7) ? . 2_665 C(8) H(3) 3.568 ? . 2_666 C(9) H(8) 3.493 ? . 2_666 C(11) H(8) 3.374 ? . 2_666 C(13) H(4) 3.385 ? . 2_666 C(15) H(1) 2.911 ? . 2_656 C(18) H(2) 3.242 ? . 1_655 C(18) H(15) 3.25(5) ? . 1_545 C(18) H(16) 3.37(6) ? . 1_545 C(19) H(2) 3.073 ? . 1_655 C(19) H(6) 3.464 ? . 1_545 C(19) H(16) 3.17(6) ? . 1_545 C(20) H(6) 3.451 ? . 1_545 C(23) H(9) 3.03(3) ? . 1_655 C(23) H(13) 2.60(5) ? . 2_755 C(23) H(15) 2.78(5) ? . 2_755 C(24) H(2) 3.157 ? . 2_656 C(24) H(6) 3.277 ? . 1_545 C(24) H(10) 2.63(5) ? . . C(24) H(12) 2.76(5) ? . . C(24) H(14) 3.10(4) ? . 2_655 H(1) F(1) 3.062 ? . 1_455 H(1) O(2) 3.421 ? . 1_455 H(1) N(1) 3.191 ? . 2_656 H(1) N(2) 2.972 ? . 2_656 H(1) C(1) 3.464 ? . 2_656 H(1) C(2) 3.325 ? . 2_656 H(1) C(15) 2.911 ? . 2_656 H(1) H(1) 2.782 ? . 2_656 H(1) H(10) 3.373 ? . 2_656 H(1) H(11) 3.278 ? . 2_656 H(1) H(12) 3.174 ? . 2_656 H(2) F(1) 3.089 ? . 1_455 H(2) F(2) 2.766 ? . 1_455 H(2) F(2) 2.914 ? . 2_656 H(2) O(3) 3.424 ? . 2_656 H(2) O(4) 2.859 ? . 2_656 H(2) N(2) 3.538 ? . 2_656 H(2) C(18) 3.242 ? . 1_455 H(2) C(19) 3.073 ? . 1_455 H(2) C(24) 3.157 ? . 2_656 H(2) H(10) 3.378 ? . 2_656 H(2) H(12) 3.045 ? . 2_656 H(3) F(2) 2.676 ? . 2_656 H(3) O(4) 3.373 ? . 1_455 H(3) O(6) 2.748 ? . 2_666 H(3) C(7) 3.400 ? . 2_666 H(3) C(8) 3.568 ? . 2_666 H(3) H(6) 3.489 ? . 2_666 H(3) H(16) 2.703 ? . 2_666 H(4) O(5) 2.556 ? . 1_565 H(4) N(2) 3.552 ? . 2_666 H(4) C(1) 3.549 ? . 2_666 H(4) C(13) 3.385 ? . 2_666 H(4) H(11) 2.686 ? . 2_666 H(5) O(2) 3.057 ? . 1_465 H(5) O(3) 3.191 ? . 1_565 H(5) N(1) 2.982 ? . 1_565 H(5) N(3) 2.943 ? . 2_665 H(5) C(2) 3.477 ? . 2_666 H(5) C(3) 3.484 ? . 2_666 H(5) H(9) 2.862 ? . 1_565 H(5) H(10) 2.736 ? . 1_565 H(5) H(13) 2.768 ? . 2_665 H(5) H(14) 2.813 ? . 2_665 H(6) F(2) 3.290 ? . 1_565 H(6) O(3) 2.632 ? . 1_565 H(6) N(3) 3.290 ? . 2_665 H(6) C(7) 3.599 ? . 2_665 H(6) C(19) 3.464 ? . 1_565 H(6) C(20) 3.451 ? . 1_565 H(6) C(24) 3.277 ? . 1_565 H(6) H(3) 3.489 ? . 2_666 H(6) H(6) 3.501 ? . 2_665 H(6) H(10) 3.584 ? . 1_565 H(6) H(14) 2.729 ? . 2_665 H(8) F(4) 2.800 ? . 2_655 H(8) O(5) 2.871 ? . 1_565 H(8) O(6) 2.790 ? . 2_666 H(8) C(9) 3.493 ? . 2_666 H(8) C(11) 3.374 ? . 2_666 H(8) H(16) 3.373 ? . 2_666 H(9) O(2) 1.87(3) ? . 1_455 H(9) O(3) 3.35(5) ? . . H(9) N(3) 3.11(4) ? . 2_655 H(9) C(23) 3.03(3) ? . 1_455 H(9) H(5) 2.862 ? . 1_545 H(9) H(13) 2.45(5) ? . 2_655 H(9) H(14) 3.10(8) ? . 2_655 H(10) O(2) 3.19(4) ? . 1_455 H(10) O(3) 1.84(5) ? . . H(10) O(4) 2.85(4) ? . . H(10) N(3) 2.94(3) ? . 2_655 H(10) C(6) 3.56(5) ? . 1_545 H(10) C(24) 2.63(5) ? . . H(10) H(1) 3.373 ? . 2_656 H(10) H(2) 3.378 ? . 2_656 H(10) H(5) 2.736 ? . 1_545 H(10) H(6) 3.584 ? . 1_545 H(10) H(13) 2.76(4) ? . 2_655 H(10) H(14) 2.43(6) ? . 2_655 H(11) F(1) 3.27(5) ? . 2_756 H(11) O(4) 3.51(6) ? . . H(11) O(5) 2.11(3) ? . 2_656 H(11) O(6) 3.33(5) ? . 2_766 H(11) C(5) 3.47(5) ? . 2_666 H(11) H(1) 3.278 ? . 2_656 H(11) H(4) 2.686 ? . 2_666 H(12) F(1) 3.52(4) ? . 2_756 H(12) O(3) 3.00(4) ? . . H(12) O(4) 1.93(6) ? . . H(12) O(5) 3.26(4) ? . 2_656 H(12) O(6) 2.93(4) ? . 2_766 H(12) C(24) 2.76(5) ? . . H(12) H(1) 3.174 ? . 2_656 H(12) H(2) 3.045 ? . 2_656 H(13) O(1) 2.82(4) ? . 2_755 H(13) O(2) 1.85(5) ? . 2_755 H(13) O(3) 3.21(4) ? . 2_655 H(13) N(1) 2.90(3) ? . 2_655 H(13) C(6) 3.44(5) ? . 2_665 H(13) C(23) 2.60(5) ? . 2_755 H(13) H(5) 2.768 ? . 2_665 H(13) H(9) 2.45(5) ? . 2_655 H(13) H(10) 2.76(4) ? . 2_655 H(14) O(2) 3.31(7) ? . 2_755 H(14) O(3) 1.90(4) ? . 2_655 H(14) N(1) 3.06(6) ? . 2_655 H(14) C(6) 3.32(7) ? . 2_665 H(14) C(7) 3.27(7) ? . 2_665 H(14) C(24) 3.10(4) ? . 2_655 H(14) H(5) 2.813 ? . 2_665 H(14) H(6) 2.729 ? . 2_665 H(14) H(9) 3.10(8) ? . 2_655 H(14) H(10) 2.43(6) ? . 2_655 H(15) F(1) 2.78(4) ? . 1_565 H(15) O(1) 1.92(5) ? . 2_755 H(15) O(2) 3.05(4) ? . 2_755 H(15) O(5) 2.98(5) ? . 1_665 H(15) O(6) 3.12(4) ? . . H(15) C(18) 3.25(5) ? . 1_565 H(15) C(23) 2.78(5) ? . 2_755 H(16) F(1) 3.04(6) ? . 1_565 H(16) F(2) 2.58(6) ? . 1_565 H(16) O(1) 3.54(6) ? . 2_755 H(16) O(5) 3.56(7) ? . 1_665 H(16) O(6) 2.16(5) ? . . H(16) C(4) 3.48(6) ? . 2_666 H(16) C(18) 3.37(6) ? . 1_565 H(16) C(19) 3.17(6) ? . 1_565 H(16) H(3) 2.703 ? . 2_666 H(16) H(8) 3.373 ? . 2_666 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__kusu112 _database_code_depnum_ccdc_archive 'CCDC 920483' #TrackingRef '16986_web_deposit_cif_file_0_TakahiroKusukawa_1358506773.1c2_3a2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H28 N4 O6 ' _chemical_formula_moiety 'C22 H28 N4 O6 ' _chemical_formula_weight 444.49 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.5243(13) _cell_length_b 11.7284(16) _cell_length_c 10.0810(14) _cell_angle_alpha 108.915(11) _cell_angle_beta 105.206(10) _cell_angle_gamma 105.742(10) _cell_volume 1145.2(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 21 _cell_measurement_theta_min 25.4 _cell_measurement_theta_max 30.0 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472.00 _exptl_absorpt_coefficient_mu 0.790 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_T_max 0.854 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 5563 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_theta_max 66.77 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 66.77 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.24 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4057 _reflns_number_gt 3186 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1569 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4057 _refine_ls_number_parameters 328 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.33 _refine_diff_density_min -0.49 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 0.99634(12) 0.80321(12) 0.36796(15) 0.0372(3) Uani 1.00 1 d . . . O(2) O 0.93576(12) 0.91212(12) 0.23852(15) 0.0375(3) Uani 1.00 1 d . . . O(3) O 0.27117(13) 0.44622(13) 0.21132(18) 0.0484(3) Uani 1.00 1 d . . . O(4) O 0.30422(12) 0.65574(12) 0.29755(17) 0.0433(3) Uani 1.00 1 d . . . O(5) O 0.79005(15) 0.81549(15) -0.08140(18) 0.0440(3) Uiso 1.00 1 d . . . O(6) O -0.94561(14) -0.16515(15) -0.32793(18) 0.0438(3) Uiso 1.00 1 d . . . N(1) N 0.04352(16) 0.56863(15) 0.2686(2) 0.0415(4) Uani 1.00 1 d . . . N(2) N 0.02582(15) 0.36097(15) 0.22592(17) 0.0322(3) Uani 1.00 1 d . . . N(3) N -0.22651(16) 0.13517(15) -0.31186(19) 0.0361(3) Uani 1.00 1 d . . . N(4) N -0.19155(17) -0.01836(17) -0.2326(2) 0.0376(3) Uani 1.00 1 d . . . C(1) C -0.15195(16) 0.42402(16) 0.26330(19) 0.0292(3) Uani 1.00 1 d . . . C(2) C -0.15876(18) 0.50681(17) 0.3897(2) 0.0344(4) Uani 1.00 1 d . . . C(3) C -0.27820(19) 0.48639(18) 0.4114(2) 0.0380(4) Uani 1.00 1 d . . . C(4) C -0.38896(18) 0.38621(18) 0.3028(2) 0.0355(4) Uani 1.00 1 d . . . C(5) C -0.61870(16) -0.00114(18) -0.1894(2) 0.0335(4) Uani 1.00 1 d . . . C(6) C -0.61671(17) -0.08786(18) -0.3148(2) 0.0359(4) Uani 1.00 1 d . . . C(7) C -0.49830(18) -0.07344(17) -0.3376(2) 0.0351(4) Uani 1.00 1 d . . . C(8) C -0.38481(16) 0.02847(16) -0.23265(19) 0.0292(3) Uani 1.00 1 d . . . C(9) C -0.26765(15) 0.22731(16) 0.01343(19) 0.0279(3) Uani 1.00 1 d . . . C(10) C -0.50268(16) 0.19586(17) 0.0546(2) 0.0312(3) Uani 1.00 1 d . . . C(11) C -0.26704(16) 0.31517(15) 0.14621(18) 0.0273(3) Uani 1.00 1 d . . . C(12) C -0.38824(16) 0.29881(17) 0.16679(19) 0.0297(3) Uani 1.00 1 d . . . C(13) C -0.38230(16) 0.12261(16) -0.09747(19) 0.0274(3) Uani 1.00 1 d . . . C(14) C -0.50315(15) 0.10658(17) -0.07638(19) 0.0286(3) Uani 1.00 1 d . . . C(15) C -0.02197(16) 0.45117(16) 0.25058(19) 0.0286(3) Uani 1.00 1 d . . . C(16) C -0.26147(16) 0.04833(15) -0.25977(18) 0.0278(3) Uani 1.00 1 d . . . C(17) C 0.92016(16) 0.85362(15) 0.32189(19) 0.0293(3) Uani 1.00 1 d . . . C(18) C 0.80383(16) 0.84150(17) 0.3676(2) 0.0335(4) Uani 1.00 1 d . . . C(19) C 0.68207(16) 0.72234(17) 0.2475(2) 0.0315(3) Uani 1.00 1 d . . . C(20) C 0.56677(16) 0.70586(18) 0.2976(2) 0.0334(4) Uani 1.00 1 d . . . C(21) C 0.44399(17) 0.58747(17) 0.1805(2) 0.0348(4) Uani 1.00 1 d . . . C(22) C 0.33137(16) 0.56129(17) 0.2331(2) 0.0334(4) Uani 1.00 1 d . . . H(1) H -0.0828 0.5787 0.4639 0.041 Uiso 1.00 1 c R . . H(2) H -0.2803 0.5424 0.5010 0.046 Uiso 1.00 1 c R . . H(3) H -0.4680 0.3740 0.3172 0.043 Uiso 1.00 1 c R . . H(4) H -0.6983 -0.0123 -0.1765 0.040 Uiso 1.00 1 c R . . H(5) H -0.6945 -0.1583 -0.3875 0.043 Uiso 1.00 1 c R . . H(6) H -0.4979 -0.1342 -0.4251 0.042 Uiso 1.00 1 c R . . H(7) H -0.1890 0.2388 -0.0018 0.033 Uiso 1.00 1 c R . . H(8) H -0.5820 0.1865 0.0678 0.037 Uiso 1.00 1 c R . . H(9) H 0.7860 0.9208 0.3827 0.040 Uiso 1.00 1 c R . . H(10) H 0.8246 0.8340 0.4644 0.040 Uiso 1.00 1 c R . . H(11) H 0.6584 0.7322 0.1523 0.038 Uiso 1.00 1 c R . . H(12) H 0.7014 0.6435 0.2283 0.038 Uiso 1.00 1 c R . . H(13) H 0.5912 0.6968 0.3933 0.040 Uiso 1.00 1 c R . . H(14) H 0.5478 0.7849 0.3167 0.040 Uiso 1.00 1 c R . . H(15) H 0.4154 0.6006 0.0880 0.042 Uiso 1.00 1 c R . . H(16) H 0.4656 0.5099 0.1542 0.042 Uiso 1.00 1 c R . . H(22) H -0.268(2) 0.193(2) -0.316(2) 0.065(7) Uiso 1.00 1 c . . . H(21) H -0.152(2) 0.152(2) -0.323(2) 0.060(7) Uiso 1.00 1 c . . . H(28) H -0.9539(16) -0.1882(16) -0.410(2) 0.022(4) Uiso 1.00 1 c . . . H(18) H 0.011(2) 0.629(2) 0.281(2) 0.043(5) Uiso 1.00 1 c . . . H(17) H 0.135(3) 0.589(3) 0.271(3) 0.092(9) Uiso 1.00 1 c . . . H(24) H -0.210(2) -0.074(2) -0.194(2) 0.042(5) Uiso 1.00 1 c . . . H(23) H -0.115(3) 0.009(2) -0.233(3) 0.068(8) Uiso 1.00 1 c . . . H(19) H 0.105(2) 0.386(2) 0.221(2) 0.049(6) Uiso 1.00 1 c . . . H(20) H -0.009(2) 0.287(2) 0.233(2) 0.039(5) Uiso 1.00 1 c . . . H(27) H -0.939(3) -0.082(3) -0.278(3) 0.088(9) Uiso 1.00 1 c . . . H(25) H 0.837(2) 0.845(2) 0.003(2) 0.041(5) Uiso 1.00 1 c . . . H(26) H 0.756(3) 0.720(3) -0.132(3) 0.090(9) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0333(6) 0.0374(6) 0.0574(8) 0.0206(5) 0.0257(6) 0.0274(5) O(2) 0.0347(6) 0.0414(7) 0.0457(7) 0.0170(5) 0.0196(5) 0.0246(5) O(3) 0.0406(7) 0.0321(6) 0.0779(10) 0.0128(5) 0.0353(7) 0.0209(6) O(4) 0.0343(6) 0.0357(6) 0.0728(9) 0.0186(5) 0.0305(6) 0.0264(6) N(1) 0.0311(8) 0.0300(7) 0.0698(11) 0.0142(6) 0.0251(8) 0.0225(7) N(2) 0.0255(7) 0.0282(7) 0.0449(8) 0.0107(6) 0.0156(6) 0.0163(6) N(3) 0.0317(8) 0.0381(8) 0.0528(9) 0.0178(6) 0.0246(7) 0.0262(7) N(4) 0.0338(8) 0.0433(8) 0.0537(9) 0.0212(7) 0.0253(7) 0.0301(7) C(1) 0.0269(8) 0.0296(8) 0.0368(8) 0.0134(6) 0.0142(6) 0.0174(7) C(2) 0.0339(9) 0.0315(8) 0.0379(9) 0.0134(7) 0.0146(7) 0.0139(7) C(3) 0.0420(10) 0.0411(9) 0.0393(9) 0.0220(8) 0.0223(8) 0.0171(8) C(4) 0.0327(9) 0.0434(9) 0.0441(9) 0.0205(8) 0.0230(8) 0.0235(8) C(5) 0.0207(7) 0.0434(9) 0.0415(9) 0.0111(7) 0.0113(7) 0.0259(8) C(6) 0.0240(8) 0.0375(9) 0.0395(9) 0.0045(7) 0.0049(7) 0.0205(7) C(7) 0.0316(9) 0.0333(8) 0.0372(9) 0.0099(7) 0.0117(7) 0.0150(7) C(8) 0.0251(8) 0.0306(8) 0.0351(8) 0.0101(6) 0.0126(7) 0.0175(7) C(9) 0.0208(7) 0.0319(8) 0.0352(8) 0.0110(6) 0.0133(6) 0.0165(7) C(10) 0.0230(8) 0.0427(9) 0.0399(9) 0.0164(7) 0.0169(7) 0.0251(7) C(11) 0.0235(8) 0.0307(8) 0.0358(8) 0.0135(6) 0.0138(6) 0.0193(7) C(12) 0.0266(8) 0.0376(9) 0.0378(9) 0.0171(7) 0.0172(7) 0.0237(7) C(13) 0.0232(7) 0.0315(8) 0.0348(8) 0.0127(6) 0.0129(6) 0.0196(7) C(14) 0.0206(7) 0.0359(8) 0.0378(9) 0.0123(6) 0.0125(6) 0.0236(7) C(15) 0.0234(8) 0.0272(7) 0.0319(8) 0.0075(6) 0.0092(6) 0.0119(6) C(16) 0.0262(8) 0.0257(7) 0.0291(7) 0.0080(6) 0.0110(6) 0.0105(6) C(17) 0.0260(8) 0.0239(7) 0.0355(8) 0.0089(6) 0.0125(6) 0.0100(6) C(18) 0.0271(8) 0.0371(9) 0.0394(9) 0.0152(7) 0.0164(7) 0.0151(7) C(19) 0.0247(8) 0.0352(8) 0.0395(9) 0.0129(7) 0.0159(7) 0.0176(7) C(20) 0.0260(8) 0.0381(9) 0.0411(9) 0.0132(7) 0.0163(7) 0.0195(7) C(21) 0.0275(9) 0.0372(9) 0.0432(9) 0.0131(7) 0.0172(7) 0.0179(8) C(22) 0.0247(8) 0.0339(8) 0.0447(9) 0.0121(7) 0.0143(7) 0.0193(7) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SIR2002 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(17) 1.258(2) yes . . O(2) C(17) 1.263(2) yes . . O(3) C(22) 1.253(2) yes . . O(4) C(22) 1.255(2) yes . . N(1) C(15) 1.305(2) yes . . N(2) C(15) 1.305(2) yes . . N(3) C(16) 1.308(2) yes . . N(4) C(16) 1.304(3) yes . . C(1) C(2) 1.366(2) yes . . C(1) C(11) 1.4371(17) yes . . C(1) C(15) 1.493(2) yes . . C(2) C(3) 1.418(3) yes . . C(3) C(4) 1.352(2) yes . . C(4) C(12) 1.424(2) yes . . C(5) C(6) 1.352(2) yes . . C(5) C(14) 1.4232(17) yes . . C(6) C(7) 1.417(3) yes . . C(7) C(8) 1.3654(18) yes . . C(8) C(13) 1.436(2) yes . . C(8) C(16) 1.488(2) yes . . C(9) C(11) 1.397(2) yes . . C(9) C(13) 1.3994(17) yes . . C(10) C(12) 1.3946(18) yes . . C(10) C(14) 1.391(2) yes . . C(11) C(12) 1.436(2) yes . . C(13) C(14) 1.435(2) yes . . C(17) C(18) 1.515(2) yes . . C(18) C(19) 1.5284(18) yes . . C(19) C(20) 1.528(2) yes . . C(20) C(21) 1.5229(18) yes . . C(21) C(22) 1.520(3) yes . . O(5) H(25) 0.77(2) no . . O(5) H(26) 0.98(3) no . . O(6) H(28) 0.75(2) no . . O(6) H(27) 0.91(3) no . . N(1) H(18) 0.87(2) no . . N(1) H(17) 1.01(3) no . . N(2) H(19) 0.90(2) no . . N(2) H(20) 0.89(2) no . . N(3) H(22) 0.93(3) no . . N(3) H(21) 0.87(3) no . . N(4) H(24) 0.87(2) no . . N(4) H(23) 0.85(3) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.940 no . . C(10) H(8) 0.940 no . . C(18) H(9) 0.980 no . . C(18) H(10) 0.980 no . . C(19) H(11) 0.980 no . . C(19) H(12) 0.980 no . . C(20) H(13) 0.980 no . . C(20) H(14) 0.980 no . . C(21) H(15) 0.980 no . . C(21) H(16) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(11) 120.62(17) yes . . . C(2) C(1) C(15) 117.90(12) yes . . . C(11) C(1) C(15) 121.48(16) yes . . . C(1) C(2) C(3) 121.28(13) yes . . . C(2) C(3) C(4) 119.82(18) yes . . . C(3) C(4) C(12) 121.3(2) yes . . . C(6) C(5) C(14) 121.57(18) yes . . . C(5) C(6) C(7) 120.50(13) yes . . . C(6) C(7) C(8) 120.19(17) yes . . . C(7) C(8) C(13) 121.19(18) yes . . . C(7) C(8) C(16) 120.46(16) yes . . . C(13) C(8) C(16) 118.28(11) yes . . . C(11) C(9) C(13) 121.71(17) yes . . . C(12) C(10) C(14) 122.05(17) yes . . . C(1) C(11) C(9) 123.77(17) yes . . . C(1) C(11) C(12) 117.46(15) yes . . . C(9) C(11) C(12) 118.75(12) yes . . . C(4) C(12) C(10) 121.21(18) yes . . . C(4) C(12) C(11) 119.46(12) yes . . . C(10) C(12) C(11) 119.32(16) yes . . . C(8) C(13) C(9) 122.80(17) yes . . . C(8) C(13) C(14) 117.87(12) yes . . . C(9) C(13) C(14) 119.33(16) yes . . . C(5) C(14) C(10) 122.50(17) yes . . . C(5) C(14) C(13) 118.68(16) yes . . . C(10) C(14) C(13) 118.81(12) yes . . . N(1) C(15) N(2) 121.13(18) yes . . . N(1) C(15) C(1) 117.96(18) yes . . . N(2) C(15) C(1) 120.89(16) yes . . . N(3) C(16) N(4) 121.62(19) yes . . . N(3) C(16) C(8) 117.20(18) yes . . . N(4) C(16) C(8) 121.18(19) yes . . . O(1) C(17) O(2) 123.01(19) yes . . . O(1) C(17) C(18) 117.96(19) yes . . . O(2) C(17) C(18) 119.03(18) yes . . . C(17) C(18) C(19) 111.69(15) yes . . . C(18) C(19) C(20) 111.66(15) yes . . . C(19) C(20) C(21) 112.92(15) yes . . . C(20) C(21) C(22) 114.10(15) yes . . . O(3) C(22) O(4) 123.3(2) yes . . . O(3) C(22) C(21) 118.10(18) yes . . . O(4) C(22) C(21) 118.61(16) yes . . . H(25) O(5) H(26) 114(2) no . . . H(28) O(6) H(27) 118(2) no . . . C(15) N(1) H(18) 122.2(15) no . . . C(15) N(1) H(17) 117(2) no . . . H(18) N(1) H(17) 120(2) no . . . C(15) N(2) H(19) 115.0(17) no . . . C(15) N(2) H(20) 121.7(17) no . . . H(19) N(2) H(20) 122(2) no . . . C(16) N(3) H(22) 122(2) no . . . C(16) N(3) H(21) 119(2) no . . . H(22) N(3) H(21) 118(2) no . . . C(16) N(4) H(24) 123.7(18) no . . . C(16) N(4) H(23) 115(2) no . . . H(24) N(4) H(23) 119(2) no . . . C(1) C(2) H(1) 119.4 no . . . C(3) C(2) H(1) 119.4 no . . . C(2) C(3) H(2) 120.1 no . . . C(4) C(3) H(2) 120.1 no . . . C(3) C(4) H(3) 119.4 no . . . C(12) C(4) H(3) 119.4 no . . . C(6) C(5) H(4) 119.2 no . . . C(14) C(5) H(4) 119.2 no . . . C(5) C(6) H(5) 119.7 no . . . C(7) C(6) H(5) 119.8 no . . . C(6) C(7) H(6) 119.9 no . . . C(8) C(7) H(6) 119.9 no . . . C(11) C(9) H(7) 119.1 no . . . C(13) C(9) H(7) 119.1 no . . . C(12) C(10) H(8) 119.0 no . . . C(14) C(10) H(8) 119.0 no . . . C(17) C(18) H(9) 109.3 no . . . C(17) C(18) H(10) 109.3 no . . . C(19) C(18) H(9) 109.3 no . . . C(19) C(18) H(10) 109.3 no . . . H(9) C(18) H(10) 107.9 no . . . C(18) C(19) H(11) 109.3 no . . . C(18) C(19) H(12) 109.3 no . . . C(20) C(19) H(11) 109.3 no . . . C(20) C(19) H(12) 109.3 no . . . H(11) C(19) H(12) 107.9 no . . . C(19) C(20) H(13) 109.0 no . . . C(19) C(20) H(14) 109.0 no . . . C(21) C(20) H(13) 109.0 no . . . C(21) C(20) H(14) 109.0 no . . . H(13) C(20) H(14) 107.8 no . . . C(20) C(21) H(15) 108.7 no . . . C(20) C(21) H(16) 108.7 no . . . C(22) C(21) H(15) 108.7 no . . . C(22) C(21) H(16) 108.7 no . . . H(15) C(21) H(16) 107.6 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(11) C(9) 179.4(2) ? . . . . C(2) C(1) C(11) C(12) 0.9(3) ? . . . . C(11) C(1) C(2) C(3) 1.6(3) ? . . . . C(2) C(1) C(15) N(1) -52.0(2) ? . . . . C(2) C(1) C(15) N(2) 126.3(2) ? . . . . C(15) C(1) C(2) C(3) -179.0(2) ? . . . . C(11) C(1) C(15) N(1) 127.4(2) ? . . . . C(11) C(1) C(15) N(2) -54.2(2) ? . . . . C(15) C(1) C(11) C(9) -0.0(2) ? . . . . C(15) C(1) C(11) C(12) -178.50(19) ? . . . . C(1) C(2) C(3) C(4) -2.5(3) ? . . . . C(2) C(3) C(4) C(12) 0.9(3) ? . . . . C(3) C(4) C(12) C(10) -179.7(2) ? . . . . C(3) C(4) C(12) C(11) 1.7(3) ? . . . . C(6) C(5) C(14) C(10) -179.1(2) ? . . . . C(6) C(5) C(14) C(13) 0.1(2) ? . . . . C(14) C(5) C(6) C(7) -0.2(3) ? . . . . C(5) C(6) C(7) C(8) 0.0(3) ? . . . . C(6) C(7) C(8) C(13) 0.2(3) ? . . . . C(6) C(7) C(8) C(16) -176.7(2) ? . . . . C(7) C(8) C(13) C(9) 179.2(2) ? . . . . C(7) C(8) C(13) C(14) -0.3(3) ? . . . . C(7) C(8) C(16) N(3) 98.6(2) ? . . . . C(7) C(8) C(16) N(4) -81.3(2) ? . . . . C(13) C(8) C(16) N(3) -78.4(2) ? . . . . C(13) C(8) C(16) N(4) 101.7(2) ? . . . . C(16) C(8) C(13) C(9) -3.9(3) ? . . . . C(16) C(8) C(13) C(14) 176.68(19) ? . . . . C(11) C(9) C(13) C(8) -177.9(2) ? . . . . C(11) C(9) C(13) C(14) 1.5(3) ? . . . . C(13) C(9) C(11) C(1) 179.97(15) ? . . . . C(13) C(9) C(11) C(12) -1.6(3) ? . . . . C(12) C(10) C(14) C(5) 178.0(2) ? . . . . C(12) C(10) C(14) C(13) -1.1(3) ? . . . . C(14) C(10) C(12) C(4) -177.5(2) ? . . . . C(14) C(10) C(12) C(11) 1.1(3) ? . . . . C(1) C(11) C(12) C(4) -2.5(3) ? . . . . C(1) C(11) C(12) C(10) 178.8(2) ? . . . . C(9) C(11) C(12) C(4) 178.9(2) ? . . . . C(9) C(11) C(12) C(10) 0.3(3) ? . . . . C(8) C(13) C(14) C(5) 0.1(2) ? . . . . C(8) C(13) C(14) C(10) 179.3(2) ? . . . . C(9) C(13) C(14) C(5) -179.4(2) ? . . . . C(9) C(13) C(14) C(10) -0.2(3) ? . . . . O(1) C(17) C(18) C(19) -93.60(19) ? . . . . O(2) C(17) C(18) C(19) 85.65(19) ? . . . . C(17) C(18) C(19) C(20) 176.85(18) ? . . . . C(18) C(19) C(20) C(21) -179.76(18) ? . . . . C(19) C(20) C(21) C(22) 174.68(18) ? . . . . C(20) C(21) C(22) O(3) -133.41(19) ? . . . . C(20) C(21) C(22) O(4) 45.8(2) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) O(6) 2.835(2) ? . 1_766 O(1) N(1) 2.860(2) ? . 1_655 O(1) N(3) 2.809(2) ? . 2_665 O(1) C(2) 3.558(2) ? . 1_655 O(2) O(5) 2.874(2) ? . . O(2) O(6) 2.768(2) ? . 2_565 O(2) N(3) 3.472(2) ? . 2_665 O(2) N(4) 2.897(2) ? . 2_665 O(2) C(16) 3.594(2) ? . 2_665 O(3) O(5) 2.714(2) ? . 2_665 O(3) N(1) 3.403(2) ? . . O(3) N(2) 2.792(2) ? . . O(3) C(3) 3.599(2) ? . 2_566 O(3) C(15) 3.516(2) ? . . O(4) N(1) 2.799(2) ? . . O(4) N(3) 2.805(2) ? . 2_565 O(4) C(7) 3.5930(18) ? . 1_666 O(5) O(2) 2.874(2) ? . . O(5) O(3) 2.714(2) ? . 2_665 O(5) N(2) 3.600(2) ? . 2_665 O(5) N(4) 2.835(3) ? . 1_665 O(5) C(10) 3.363(2) ? . 2_565 O(6) O(1) 2.835(2) ? . 1_344 O(6) O(2) 2.768(2) ? . 2_565 O(6) N(2) 2.840(2) ? . 2_455 O(6) C(5) 3.378(2) ? . . O(6) C(17) 3.568(2) ? . 1_344 O(6) C(17) 3.564(2) ? . 2_565 N(1) O(1) 2.860(2) ? . 1_455 N(1) O(3) 3.403(2) ? . . N(1) O(4) 2.799(2) ? . . N(1) N(3) 3.356(2) ? . 2_565 N(1) C(22) 3.449(2) ? . . N(2) O(3) 2.792(2) ? . . N(2) O(5) 3.600(2) ? . 2_665 N(2) O(6) 2.840(2) ? . 2_455 N(2) C(2) 3.386(2) ? . 2_566 N(2) C(3) 3.519(2) ? . 2_566 N(3) O(1) 2.809(2) ? . 2_665 N(3) O(2) 3.472(2) ? . 2_665 N(3) O(4) 2.805(2) ? . 2_565 N(3) N(1) 3.356(2) ? . 2_565 N(3) C(6) 3.503(2) ? . 2_454 N(3) C(17) 3.526(2) ? . 2_665 N(4) O(2) 2.897(2) ? . 2_665 N(4) O(5) 2.835(3) ? . 1_445 C(2) O(1) 3.558(2) ? . 1_455 C(2) N(2) 3.386(2) ? . 2_566 C(2) C(15) 3.471(2) ? . 2_566 C(3) O(3) 3.599(2) ? . 2_566 C(3) N(2) 3.519(2) ? . 2_566 C(4) C(6) 3.558(3) ? . 2_455 C(5) O(6) 3.378(2) ? . . C(5) C(10) 3.431(3) ? . 2_455 C(5) C(12) 3.592(3) ? . 2_455 C(5) C(14) 3.435(3) ? . 2_455 C(6) N(3) 3.503(2) ? . 2_454 C(6) C(4) 3.558(3) ? . 2_455 C(6) C(10) 3.404(3) ? . 2_455 C(6) C(12) 3.283(3) ? . 2_455 C(7) O(4) 3.5930(18) ? . 1_444 C(7) C(10) 3.585(3) ? . 2_455 C(10) O(5) 3.363(2) ? . 2_565 C(10) C(5) 3.431(3) ? . 2_455 C(10) C(6) 3.404(3) ? . 2_455 C(10) C(7) 3.585(3) ? . 2_455 C(12) C(5) 3.592(3) ? . 2_455 C(12) C(6) 3.283(3) ? . 2_455 C(14) C(5) 3.435(3) ? . 2_455 C(14) C(14) 3.341(3) ? . 2_455 C(15) O(3) 3.516(2) ? . . C(15) C(2) 3.471(2) ? . 2_566 C(16) O(2) 3.594(2) ? . 2_665 C(17) O(6) 3.568(2) ? . 1_766 C(17) O(6) 3.564(2) ? . 2_565 C(17) N(3) 3.526(2) ? . 2_665 C(22) N(1) 3.449(2) ? . . O(1) H(1) 3.084 ? . 1_655 O(1) H(5) 3.574 ? . 1_766 O(1) H(9) 3.178 ? . 2_776 O(1) H(22) 3.30(3) ? . 2_665 O(1) H(21) 1.94(3) ? . 2_665 O(1) H(28) 2.13(2) ? . 1_766 O(1) H(18) 2.02(2) ? . 1_655 O(1) H(17) 3.35(4) ? . 1_655 O(1) H(23) 3.14(3) ? . 2_665 O(1) H(27) 3.17(3) ? . 1_766 O(2) H(4) 3.253 ? . 2_565 O(2) H(10) 3.299 ? . 2_776 O(2) H(21) 2.80(3) ? . 2_665 O(2) H(28) 3.054(18) ? . 2_565 O(2) H(24) 3.45(2) ? . 2_665 O(2) H(23) 2.05(3) ? . 2_665 O(2) H(27) 1.89(3) ? . 2_565 O(2) H(25) 2.11(2) ? . . O(2) H(26) 3.36(2) ? . . O(3) H(2) 2.832 ? . 2_566 O(3) H(3) 3.343 ? . 1_655 O(3) H(17) 2.62(4) ? . . O(3) H(19) 1.89(2) ? . . O(3) H(20) 3.37(2) ? . . O(3) H(25) 3.06(2) ? . 2_665 O(3) H(26) 1.75(3) ? . 2_665 O(4) H(2) 3.550 ? . 2_566 O(4) H(5) 3.210 ? . 1_666 O(4) H(6) 2.868 ? . 1_666 O(4) H(22) 1.89(3) ? . 2_565 O(4) H(21) 3.20(3) ? . 2_565 O(4) H(18) 3.26(2) ? . . O(4) H(17) 1.80(3) ? . . O(4) H(19) 3.07(2) ? . . O(5) H(3) 3.440 ? . 2_565 O(5) H(4) 3.476 ? . 2_565 O(5) H(8) 2.432 ? . 2_565 O(5) H(11) 3.372 ? . . O(5) H(24) 1.98(2) ? . 1_665 O(5) H(23) 3.24(3) ? . 1_665 O(5) H(19) 3.05(2) ? . 2_665 O(5) H(20) 3.56(2) ? . 2_665 O(5) H(27) 3.51(2) ? . 2_565 O(6) H(1) 2.743 ? . 1_444 O(6) H(4) 2.615 ? . . O(6) H(5) 3.092 ? . . O(6) H(9) 3.255 ? . 2_565 O(6) H(10) 2.908 ? . 1_344 O(6) H(23) 3.29(3) ? . 1_455 O(6) H(19) 3.40(2) ? . 2_455 O(6) H(20) 1.99(2) ? . 2_455 N(1) H(22) 3.05(2) ? . 2_565 N(1) H(21) 2.97(2) ? . 2_565 N(1) H(28) 3.545(19) ? . 1_666 N(2) H(1) 2.819 ? . 2_566 N(2) H(2) 3.067 ? . 2_566 N(2) H(28) 3.25(2) ? . 2_455 N(2) H(27) 3.41(4) ? . 2_455 N(2) H(26) 3.17(3) ? . 2_665 N(3) H(5) 3.050 ? . 2_454 N(3) H(6) 3.558 ? . 2_454 N(3) H(9) 3.351 ? . 1_444 N(3) H(18) 3.03(2) ? . 2_565 N(3) H(17) 2.97(3) ? . 2_565 N(4) H(10) 3.067 ? . 1_444 N(4) H(27) 3.30(3) ? . 1_655 N(4) H(25) 3.26(2) ? . 1_445 N(4) H(26) 3.49(4) ? . 1_445 C(1) H(1) 3.330 ? . 2_566 C(1) H(12) 3.499 ? . 1_455 C(2) H(1) 3.355 ? . 2_566 C(2) H(12) 3.087 ? . 1_455 C(2) H(28) 3.268(14) ? . 1_666 C(2) H(19) 3.54(2) ? . 2_566 C(2) H(20) 3.418(17) ? . 2_566 C(3) H(12) 3.011 ? . 1_455 C(3) H(13) 3.249 ? . 1_455 C(3) H(16) 3.522 ? . 1_455 C(3) H(19) 3.30(2) ? . 2_566 C(4) H(5) 3.354 ? . 2_455 C(4) H(12) 3.306 ? . 1_455 C(4) H(13) 3.545 ? . 1_455 C(4) H(16) 2.927 ? . 1_455 C(5) H(9) 2.933 ? . 2_565 C(5) H(11) 3.226 ? . 2_565 C(5) H(14) 3.207 ? . 2_565 C(5) H(28) 3.523(15) ? . . C(5) H(27) 3.34(3) ? . . C(6) H(9) 3.217 ? . 2_565 C(6) H(14) 3.432 ? . 2_565 C(6) H(22) 3.27(2) ? . 2_454 C(6) H(28) 3.499(18) ? . . C(7) H(3) 3.519 ? . 2_455 C(7) H(8) 3.420 ? . 2_455 C(7) H(14) 3.590 ? . 1_444 C(7) H(14) 3.532 ? . 2_565 C(7) H(22) 3.36(2) ? . 2_454 C(8) H(8) 3.434 ? . 2_455 C(8) H(14) 3.411 ? . 2_565 C(9) H(4) 3.422 ? . 2_455 C(9) H(15) 3.211 ? . 2_565 C(10) H(11) 2.877 ? . 2_565 C(10) H(15) 3.233 ? . 2_565 C(10) H(26) 3.52(3) ? . 2_565 C(11) H(4) 3.588 ? . 2_455 C(11) H(5) 3.539 ? . 2_455 C(11) H(15) 3.128 ? . 2_565 C(12) H(5) 3.270 ? . 2_455 C(12) H(15) 3.135 ? . 2_565 C(12) H(16) 3.367 ? . 1_455 C(13) H(4) 3.434 ? . 2_455 C(13) H(14) 3.188 ? . 2_565 C(13) H(15) 3.344 ? . 2_565 C(14) H(11) 3.069 ? . 2_565 C(14) H(14) 3.075 ? . 2_565 C(14) H(15) 3.357 ? . 2_565 C(15) H(1) 2.988 ? . 2_566 C(17) H(9) 3.475 ? . 2_776 C(17) H(10) 3.525 ? . 2_776 C(17) H(21) 2.69(3) ? . 2_665 C(17) H(28) 2.98(2) ? . 1_766 C(17) H(18) 3.04(2) ? . 1_655 C(17) H(23) 2.91(3) ? . 2_665 C(17) H(27) 2.81(4) ? . 2_565 C(17) H(25) 3.07(2) ? . . C(18) H(4) 3.435 ? . 2_565 C(18) H(28) 3.27(2) ? . 1_766 C(18) H(23) 3.58(2) ? . 1_666 C(18) H(27) 3.35(4) ? . 2_565 C(20) H(6) 3.215 ? . 1_666 C(21) H(3) 3.476 ? . 1_655 C(21) H(26) 3.51(3) ? . 2_665 C(22) H(2) 3.401 ? . 2_566 C(22) H(22) 3.07(3) ? . 2_565 C(22) H(17) 2.48(4) ? . . C(22) H(19) 2.79(2) ? . . C(22) H(26) 2.90(3) ? . 2_665 H(1) O(1) 3.084 ? . 1_455 H(1) O(6) 2.743 ? . 1_666 H(1) N(2) 2.819 ? . 2_566 H(1) C(1) 3.330 ? . 2_566 H(1) C(2) 3.355 ? . 2_566 H(1) C(15) 2.988 ? . 2_566 H(1) H(1) 3.105 ? . 2_566 H(1) H(10) 3.439 ? . 1_455 H(1) H(12) 3.391 ? . 1_455 H(1) H(28) 2.418 ? . 1_666 H(1) H(19) 3.161 ? . 2_566 H(1) H(20) 2.684 ? . 2_566 H(1) H(27) 3.578 ? . 1_666 H(2) O(3) 2.832 ? . 2_566 H(2) O(4) 3.550 ? . 2_566 H(2) N(2) 3.067 ? . 2_566 H(2) C(22) 3.401 ? . 2_566 H(2) H(10) 3.479 ? . 1_455 H(2) H(12) 3.309 ? . 1_455 H(2) H(13) 2.922 ? . 1_455 H(2) H(17) 3.485 ? . 2_566 H(2) H(19) 2.690 ? . 2_566 H(2) H(20) 3.246 ? . 2_566 H(2) H(26) 3.450 ? . 1_456 H(3) O(3) 3.343 ? . 1_455 H(3) O(5) 3.440 ? . 2_565 H(3) C(7) 3.519 ? . 2_455 H(3) C(21) 3.476 ? . 1_455 H(3) H(6) 3.295 ? . 2_455 H(3) H(13) 3.440 ? . 1_455 H(3) H(16) 2.744 ? . 1_455 H(3) H(26) 3.025 ? . 2_565 H(4) O(2) 3.253 ? . 2_565 H(4) O(5) 3.476 ? . 2_565 H(4) O(6) 2.615 ? . . H(4) C(9) 3.422 ? . 2_455 H(4) C(11) 3.588 ? . 2_455 H(4) C(13) 3.434 ? . 2_455 H(4) C(18) 3.435 ? . 2_565 H(4) H(9) 2.724 ? . 2_565 H(4) H(11) 3.108 ? . 2_565 H(4) H(28) 2.895 ? . . H(4) H(27) 2.478 ? . . H(4) H(25) 3.228 ? . 2_565 H(5) O(1) 3.574 ? . 1_344 H(5) O(4) 3.210 ? . 1_444 H(5) O(6) 3.092 ? . . H(5) N(3) 3.050 ? . 2_454 H(5) C(4) 3.354 ? . 2_455 H(5) C(11) 3.539 ? . 2_455 H(5) C(12) 3.270 ? . 2_455 H(5) H(9) 3.224 ? . 2_565 H(5) H(22) 2.782 ? . 2_454 H(5) H(21) 3.020 ? . 2_454 H(5) H(28) 2.853 ? . . H(5) H(18) 3.596 ? . 1_444 H(5) H(17) 3.344 ? . 1_444 H(5) H(27) 3.508 ? . . H(6) O(4) 2.868 ? . 1_444 H(6) N(3) 3.558 ? . 2_454 H(6) C(20) 3.215 ? . 1_444 H(6) H(3) 3.295 ? . 2_455 H(6) H(13) 2.840 ? . 1_444 H(6) H(14) 2.709 ? . 1_444 H(6) H(22) 2.949 ? . 2_454 H(8) O(5) 2.432 ? . 2_565 H(8) C(7) 3.420 ? . 2_455 H(8) C(8) 3.434 ? . 2_455 H(8) H(11) 2.722 ? . 2_565 H(8) H(16) 3.454 ? . 1_455 H(8) H(24) 3.169 ? . 2_455 H(8) H(25) 2.726 ? . 2_565 H(8) H(26) 2.660 ? . 2_565 H(9) O(1) 3.178 ? . 2_776 H(9) O(6) 3.255 ? . 2_565 H(9) N(3) 3.351 ? . 1_666 H(9) C(5) 2.933 ? . 2_565 H(9) C(6) 3.217 ? . 2_565 H(9) C(17) 3.475 ? . 2_776 H(9) H(4) 2.724 ? . 2_565 H(9) H(5) 3.224 ? . 2_565 H(9) H(21) 3.048 ? . 1_666 H(9) H(28) 3.087 ? . 2_565 H(9) H(23) 3.436 ? . 1_666 H(9) H(27) 2.871 ? . 2_565 H(10) O(2) 3.299 ? . 2_776 H(10) O(6) 2.908 ? . 1_766 H(10) N(4) 3.067 ? . 1_666 H(10) C(17) 3.525 ? . 2_776 H(10) H(1) 3.439 ? . 1_655 H(10) H(2) 3.479 ? . 1_655 H(10) H(21) 3.545 ? . 1_666 H(10) H(28) 2.659 ? . 1_766 H(10) H(24) 3.431 ? . 1_666 H(10) H(23) 2.837 ? . 1_666 H(10) H(27) 2.883 ? . 1_766 H(11) O(5) 3.372 ? . . H(11) C(5) 3.226 ? . 2_565 H(11) C(10) 2.877 ? . 2_565 H(11) C(14) 3.069 ? . 2_565 H(11) H(4) 3.108 ? . 2_565 H(11) H(8) 2.722 ? . 2_565 H(11) H(15) 3.580 ? . 2_665 H(11) H(16) 3.074 ? . 2_665 H(11) H(25) 3.117 ? . . H(11) H(26) 3.321 ? . . H(12) C(1) 3.499 ? . 1_655 H(12) C(2) 3.087 ? . 1_655 H(12) C(3) 3.011 ? . 1_655 H(12) C(4) 3.306 ? . 1_655 H(12) H(1) 3.391 ? . 1_655 H(12) H(2) 3.309 ? . 1_655 H(12) H(15) 3.149 ? . 2_665 H(12) H(16) 3.398 ? . 2_665 H(12) H(18) 3.531 ? . 1_655 H(13) C(3) 3.249 ? . 1_655 H(13) C(4) 3.545 ? . 1_655 H(13) H(2) 2.922 ? . 1_655 H(13) H(3) 3.440 ? . 1_655 H(13) H(6) 2.840 ? . 1_666 H(14) C(5) 3.207 ? . 2_565 H(14) C(6) 3.432 ? . 2_565 H(14) C(7) 3.590 ? . 1_666 H(14) C(7) 3.532 ? . 2_565 H(14) C(8) 3.411 ? . 2_565 H(14) C(13) 3.188 ? . 2_565 H(14) C(14) 3.075 ? . 2_565 H(14) H(6) 2.709 ? . 1_666 H(14) H(22) 3.300 ? . 2_565 H(15) C(9) 3.211 ? . 2_565 H(15) C(10) 3.233 ? . 2_565 H(15) C(11) 3.128 ? . 2_565 H(15) C(12) 3.135 ? . 2_565 H(15) C(13) 3.344 ? . 2_565 H(15) C(14) 3.357 ? . 2_565 H(15) H(11) 3.580 ? . 2_665 H(15) H(12) 3.149 ? . 2_665 H(15) H(16) 3.193 ? . 2_665 H(16) C(3) 3.522 ? . 1_655 H(16) C(4) 2.927 ? . 1_655 H(16) C(12) 3.367 ? . 1_655 H(16) H(3) 2.744 ? . 1_655 H(16) H(8) 3.454 ? . 1_655 H(16) H(11) 3.074 ? . 2_665 H(16) H(12) 3.398 ? . 2_665 H(16) H(15) 3.193 ? . 2_665 H(16) H(16) 3.358 ? . 2_665 H(16) H(26) 3.068 ? . 2_665 H(22) O(1) 3.30(3) ? . 2_665 H(22) O(4) 1.89(3) ? . 2_565 H(22) N(1) 3.05(2) ? . 2_565 H(22) C(6) 3.27(2) ? . 2_454 H(22) C(7) 3.36(2) ? . 2_454 H(22) C(22) 3.07(3) ? . 2_565 H(22) H(5) 2.782 ? . 2_454 H(22) H(6) 2.949 ? . 2_454 H(22) H(14) 3.300 ? . 2_565 H(22) H(18) 2.98(3) ? . 2_565 H(22) H(17) 2.42(4) ? . 2_565 H(21) O(1) 1.94(3) ? . 2_665 H(21) O(2) 2.80(3) ? . 2_665 H(21) O(4) 3.20(3) ? . 2_565 H(21) N(1) 2.97(2) ? . 2_565 H(21) C(17) 2.69(3) ? . 2_665 H(21) H(5) 3.020 ? . 2_454 H(21) H(9) 3.048 ? . 1_444 H(21) H(10) 3.545 ? . 1_444 H(21) H(28) 3.33(4) ? . 2_454 H(21) H(18) 2.46(3) ? . 2_565 H(21) H(17) 2.85(4) ? . 2_565 H(28) O(1) 2.13(2) ? . 1_344 H(28) O(2) 3.054(18) ? . 2_565 H(28) N(1) 3.545(19) ? . 1_444 H(28) N(2) 3.25(2) ? . 2_455 H(28) C(2) 3.268(14) ? . 1_444 H(28) C(5) 3.523(15) ? . . H(28) C(6) 3.499(18) ? . . H(28) C(17) 2.98(2) ? . 1_344 H(28) C(18) 3.27(2) ? . 1_344 H(28) H(1) 2.418 ? . 1_444 H(28) H(4) 2.895 ? . . H(28) H(5) 2.853 ? . . H(28) H(9) 3.087 ? . 2_565 H(28) H(10) 2.659 ? . 1_344 H(28) H(21) 3.33(4) ? . 2_454 H(28) H(18) 3.00(2) ? . 1_444 H(28) H(20) 2.48(3) ? . 2_455 H(18) O(1) 2.02(2) ? . 1_455 H(18) O(4) 3.26(2) ? . . H(18) N(3) 3.03(2) ? . 2_565 H(18) C(17) 3.04(2) ? . 1_455 H(18) H(5) 3.596 ? . 1_666 H(18) H(12) 3.531 ? . 1_455 H(18) H(22) 2.98(3) ? . 2_565 H(18) H(21) 2.46(3) ? . 2_565 H(18) H(28) 3.00(2) ? . 1_666 H(17) O(1) 3.35(4) ? . 1_455 H(17) O(3) 2.62(4) ? . . H(17) O(4) 1.80(3) ? . . H(17) N(3) 2.97(3) ? . 2_565 H(17) C(22) 2.48(4) ? . . H(17) H(2) 3.485 ? . 2_566 H(17) H(5) 3.344 ? . 1_666 H(17) H(22) 2.42(4) ? . 2_565 H(17) H(21) 2.85(4) ? . 2_565 H(24) O(2) 3.45(2) ? . 2_665 H(24) O(5) 1.98(2) ? . 1_445 H(24) H(8) 3.169 ? . 2_455 H(24) H(10) 3.431 ? . 1_444 H(24) H(27) 3.47(4) ? . 1_655 H(24) H(25) 2.46(4) ? . 1_445 H(24) H(26) 2.64(5) ? . 1_445 H(23) O(1) 3.14(3) ? . 2_665 H(23) O(2) 2.05(3) ? . 2_665 H(23) O(5) 3.24(3) ? . 1_445 H(23) O(6) 3.29(3) ? . 1_655 H(23) C(17) 2.91(3) ? . 2_665 H(23) C(18) 3.58(2) ? . 1_444 H(23) H(9) 3.436 ? . 1_444 H(23) H(10) 2.837 ? . 1_444 H(23) H(27) 2.61(5) ? . 1_655 H(23) H(25) 3.57(4) ? . 1_445 H(23) H(25) 3.03(3) ? . 2_665 H(19) O(3) 1.89(2) ? . . H(19) O(4) 3.07(2) ? . . H(19) O(5) 3.05(2) ? . 2_665 H(19) O(6) 3.40(2) ? . 2_455 H(19) C(2) 3.54(2) ? . 2_566 H(19) C(3) 3.30(2) ? . 2_566 H(19) C(22) 2.79(2) ? . . H(19) H(1) 3.161 ? . 2_566 H(19) H(2) 2.690 ? . 2_566 H(19) H(25) 3.26(3) ? . 2_665 H(19) H(26) 2.45(5) ? . 2_665 H(20) O(3) 3.37(2) ? . . H(20) O(5) 3.56(2) ? . 2_665 H(20) O(6) 1.99(2) ? . 2_455 H(20) C(2) 3.418(17) ? . 2_566 H(20) H(1) 2.684 ? . 2_566 H(20) H(2) 3.246 ? . 2_566 H(20) H(28) 2.48(3) ? . 2_455 H(20) H(27) 2.53(4) ? . 2_455 H(20) H(26) 3.35(4) ? . 2_665 H(27) O(1) 3.17(3) ? . 1_344 H(27) O(2) 1.89(4) ? . 2_565 H(27) O(5) 3.51(2) ? . 2_565 H(27) N(2) 3.41(4) ? . 2_455 H(27) N(4) 3.30(3) ? . 1_455 H(27) C(5) 3.34(3) ? . . H(27) C(17) 2.81(4) ? . 2_565 H(27) C(18) 3.35(4) ? . 2_565 H(27) H(1) 3.578 ? . 1_444 H(27) H(4) 2.478 ? . . H(27) H(5) 3.508 ? . . H(27) H(9) 2.871 ? . 2_565 H(27) H(10) 2.883 ? . 1_344 H(27) H(24) 3.47(4) ? . 1_455 H(27) H(23) 2.61(5) ? . 1_455 H(27) H(20) 2.53(4) ? . 2_455 H(27) H(25) 2.88(3) ? . 2_565 H(25) O(2) 2.11(2) ? . . H(25) O(3) 3.06(2) ? . 2_665 H(25) N(4) 3.26(2) ? . 1_665 H(25) C(17) 3.07(2) ? . . H(25) H(4) 3.228 ? . 2_565 H(25) H(8) 2.726 ? . 2_565 H(25) H(11) 3.117 ? . . H(25) H(24) 2.46(4) ? . 1_665 H(25) H(23) 3.57(4) ? . 1_665 H(25) H(23) 3.03(3) ? . 2_665 H(25) H(19) 3.26(3) ? . 2_665 H(25) H(27) 2.88(3) ? . 2_565 H(26) O(2) 3.36(2) ? . . H(26) O(3) 1.75(3) ? . 2_665 H(26) N(2) 3.17(3) ? . 2_665 H(26) N(4) 3.49(4) ? . 1_665 H(26) C(10) 3.52(3) ? . 2_565 H(26) C(21) 3.51(3) ? . 2_665 H(26) C(22) 2.90(3) ? . 2_665 H(26) H(2) 3.450 ? . 1_654 H(26) H(3) 3.025 ? . 2_565 H(26) H(8) 2.660 ? . 2_565 H(26) H(11) 3.321 ? . . H(26) H(16) 3.068 ? . 2_665 H(26) H(24) 2.64(5) ? . 1_665 H(26) H(19) 2.45(5) ? . 2_665 H(26) H(20) 3.35(4) ? . 2_665 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__kusu110 _database_code_depnum_ccdc_archive 'CCDC 920484' #TrackingRef '16987_web_deposit_cif_file_0_TakahiroKusukawa_1358506911.1c2_3b2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H32 N4 O6 ' _chemical_formula_moiety 'C24 H32 N4 O6 ' _chemical_formula_weight 472.54 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 12.054(3) _cell_length_b 12.563(4) _cell_length_c 9.714(3) _cell_angle_alpha 105.63(2) _cell_angle_beta 109.560(20) _cell_angle_gamma 102.83(2) _cell_volume 1253.3(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 25.5 _cell_measurement_theta_max 30.0 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504.00 _exptl_absorpt_coefficient_mu 0.751 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.861 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 6054 _diffrn_reflns_av_R_equivalents 0.128 _diffrn_reflns_theta_max 66.74 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 66.74 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -21.56 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4398 _reflns_number_gt 3576 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.2256 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4398 _refine_ls_number_parameters 330 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1124P)^2^+0.8939P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.69 _refine_diff_density_min -0.47 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 0.60135(18) 0.33463(16) 0.2876(2) 0.0467(5) Uani 1.00 1 d . . . O(2) O 0.40100(19) 0.31072(17) 0.2313(3) 0.0546(6) Uani 1.00 1 d . . . O(3) O 0.19420(19) -0.49859(17) 0.1700(2) 0.0478(5) Uani 1.00 1 d . . . O(4) O 0.05895(18) -0.45520(16) 0.2647(2) 0.0453(5) Uani 1.00 1 d . . . O(5) O 0.8167(2) 0.28443(18) 0.4068(2) 0.0516(5) Uiso 1.00 1 d . . . O(6) O 1.1565(2) 1.39836(19) 0.8435(2) 0.0550(5) Uiso 1.00 1 d . . . N(1) N 0.8351(2) 0.7009(2) 0.7670(3) 0.0436(5) Uani 1.00 1 d . . . N(2) N 1.0090(2) 0.6896(2) 0.7304(3) 0.0432(5) Uani 1.00 1 d . . . N(3) N 0.4452(2) 0.5333(2) 0.2173(3) 0.0478(6) Uani 1.00 1 d . . . N(4) N 0.6365(2) 0.5382(2) 0.2275(3) 0.0407(5) Uani 1.00 1 d . . . C(1) C 0.9564(2) 0.8649(2) 0.7304(3) 0.0367(5) Uani 1.00 1 d . . . C(2) C 1.0599(2) 0.9563(2) 0.8442(3) 0.0435(6) Uani 1.00 1 d . . . C(3) C 1.0848(2) 1.0710(2) 0.8380(3) 0.0449(6) Uani 1.00 1 d . . . C(4) C 1.0072(2) 1.0895(2) 0.7160(3) 0.0408(6) Uani 1.00 1 d . . . C(5) C 0.6335(2) 0.9364(2) 0.2103(3) 0.0413(6) Uani 1.00 1 d . . . C(6) C 0.5307(2) 0.8463(2) 0.0947(3) 0.0469(6) Uani 1.00 1 d . . . C(7) C 0.5026(2) 0.7318(2) 0.1009(3) 0.0438(6) Uani 1.00 1 d . . . C(8) C 0.5800(2) 0.7104(2) 0.2209(3) 0.0367(5) Uani 1.00 1 d . . . C(9) C 0.7672(2) 0.7881(2) 0.4773(3) 0.0354(5) Uani 1.00 1 d . . . C(10) C 0.8197(2) 1.0120(2) 0.4637(3) 0.0375(5) Uani 1.00 1 d . . . C(11) C 0.6889(2) 0.8035(2) 0.3475(3) 0.0346(5) Uani 1.00 1 d . . . C(12) C 0.7146(2) 0.9194(2) 0.3414(3) 0.0358(5) Uani 1.00 1 d . . . C(13) C 0.8720(2) 0.8806(2) 0.5993(3) 0.0345(5) Uani 1.00 1 d . . . C(14) C 0.8992(2) 0.9960(2) 0.5928(3) 0.0359(5) Uani 1.00 1 d . . . C(15) C 0.9322(2) 0.7460(2) 0.7427(3) 0.0363(5) Uani 1.00 1 d . . . C(16) C 0.5525(2) 0.5883(2) 0.2216(3) 0.0373(5) Uani 1.00 1 d . . . C(17) C 0.4974(2) 0.2857(2) 0.2845(3) 0.0403(6) Uani 1.00 1 d . . . C(18) C 0.4873(2) 0.1887(2) 0.3507(3) 0.0446(6) Uani 1.00 1 d . . . C(19) C 0.3774(2) 0.0767(2) 0.2353(3) 0.0420(6) Uani 1.00 1 d . . . C(20) C 0.3662(2) -0.0205(2) 0.2999(3) 0.0407(6) Uani 1.00 1 d . . . C(21) C 0.2571(2) -0.1319(2) 0.1842(3) 0.0425(6) Uani 1.00 1 d . . . C(22) C 0.2460(2) -0.2309(2) 0.2470(3) 0.0422(6) Uani 1.00 1 d . . . C(23) C 0.1321(2) -0.3396(2) 0.1305(3) 0.0441(6) Uani 1.00 1 d . . . C(24) C 0.1272(2) -0.4389(2) 0.1924(3) 0.0393(6) Uani 1.00 1 d . . . H(1) H 1.1155 0.9438 0.9278 0.052 Uiso 1.00 1 c R . . H(2) H 1.1554 1.1339 0.9188 0.054 Uiso 1.00 1 c R . . H(3) H 1.0249 1.1653 0.7128 0.049 Uiso 1.00 1 c R . . H(4) H 0.6515 1.0111 0.2039 0.050 Uiso 1.00 1 c R . . H(5) H 0.4776 0.8594 0.0098 0.056 Uiso 1.00 1 c R . . H(6) H 0.4299 0.6706 0.0214 0.052 Uiso 1.00 1 c R . . H(7) H 0.7490 0.7131 0.4831 0.043 Uiso 1.00 1 c R . . H(8) H 0.8371 1.0873 0.4587 0.045 Uiso 1.00 1 c R . . H(9) H 0.4771 0.2167 0.4486 0.054 Uiso 1.00 1 c R . . H(10) H 0.5652 0.1710 0.3759 0.054 Uiso 1.00 1 c R . . H(11) H 0.2996 0.0946 0.2099 0.050 Uiso 1.00 1 c R . . H(12) H 0.3877 0.0488 0.1375 0.050 Uiso 1.00 1 c R . . H(13) H 0.3553 0.0071 0.3973 0.049 Uiso 1.00 1 c R . . H(14) H 0.4441 -0.0383 0.3257 0.049 Uiso 1.00 1 c R . . H(15) H 0.2675 -0.1587 0.0862 0.051 Uiso 1.00 1 c R . . H(16) H 0.1792 -0.1142 0.1594 0.051 Uiso 1.00 1 c R . . H(17) H 0.3221 -0.2517 0.2670 0.051 Uiso 1.00 1 c R . . H(18) H 0.2389 -0.2036 0.3471 0.051 Uiso 1.00 1 c R . . H(19) H 0.0555 -0.3203 0.1147 0.053 Uiso 1.00 1 c R . . H(20) H 0.1369 -0.3650 0.0286 0.053 Uiso 1.00 1 c R . . H(25) H 0.427(3) 0.458(3) 0.217(4) 0.063(10) Uiso 1.00 1 c . . . H(26) H 0.386(3) 0.567(3) 0.215(4) 0.053(9) Uiso 1.00 1 c . . . H(27) H 0.624(3) 0.471(3) 0.244(4) 0.052(9) Uiso 1.00 1 c . . . H(28) H 0.706(3) 0.567(2) 0.219(4) 0.050(8) Uiso 1.00 1 c . . . H(23) H 0.987(3) 0.618(3) 0.735(4) 0.056(9) Uiso 1.00 1 c . . . H(21) H 0.825(3) 0.627(3) 0.781(4) 0.055(9) Uiso 1.00 1 c . . . H(22) H 0.776(3) 0.732(2) 0.774(3) 0.044(8) Uiso 1.00 1 c . . . H(24) H 1.063(3) 0.712(3) 0.695(4) 0.052(9) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0346(10) 0.0394(10) 0.0678(13) 0.0097(8) 0.0209(9) 0.0257(9) O(2) 0.0401(11) 0.0401(10) 0.0931(17) 0.0153(8) 0.0316(11) 0.0331(11) O(3) 0.0417(10) 0.0428(10) 0.0777(14) 0.0211(8) 0.0325(10) 0.0354(10) O(4) 0.0438(10) 0.0369(9) 0.0640(12) 0.0156(8) 0.0279(9) 0.0237(8) N(1) 0.0419(12) 0.0368(12) 0.0665(15) 0.0182(10) 0.0286(11) 0.0293(11) N(2) 0.0400(12) 0.0358(12) 0.0637(15) 0.0143(9) 0.0269(11) 0.0255(11) N(3) 0.0344(12) 0.0353(12) 0.0774(18) 0.0116(10) 0.0245(12) 0.0254(11) N(4) 0.0367(12) 0.0257(10) 0.0616(14) 0.0088(9) 0.0256(11) 0.0145(10) C(1) 0.0356(13) 0.0297(12) 0.0461(14) 0.0099(10) 0.0191(11) 0.0146(10) C(2) 0.0389(14) 0.0367(13) 0.0486(15) 0.0079(11) 0.0159(12) 0.0140(11) C(3) 0.0412(14) 0.0297(12) 0.0516(16) 0.0028(10) 0.0200(12) 0.0043(11) C(4) 0.0435(14) 0.0239(11) 0.0554(16) 0.0083(10) 0.0267(13) 0.0104(11) C(5) 0.0496(15) 0.0363(13) 0.0516(15) 0.0201(11) 0.0279(13) 0.0234(12) C(6) 0.0520(16) 0.0467(15) 0.0491(15) 0.0233(13) 0.0218(13) 0.0227(13) C(7) 0.0419(14) 0.0398(14) 0.0463(15) 0.0138(11) 0.0176(12) 0.0129(11) C(8) 0.0369(13) 0.0292(12) 0.0458(14) 0.0115(10) 0.0202(11) 0.0131(10) C(9) 0.0361(12) 0.0235(11) 0.0496(14) 0.0096(9) 0.0198(11) 0.0161(10) C(10) 0.0451(14) 0.0239(11) 0.0525(15) 0.0123(10) 0.0285(12) 0.0171(10) C(11) 0.0343(12) 0.0269(11) 0.0477(14) 0.0114(9) 0.0221(11) 0.0147(10) C(12) 0.0403(13) 0.0304(12) 0.0483(14) 0.0162(10) 0.0259(11) 0.0191(10) C(13) 0.0356(12) 0.0243(11) 0.0459(13) 0.0092(9) 0.0207(11) 0.0127(10) C(14) 0.0383(13) 0.0246(11) 0.0520(15) 0.0112(9) 0.0275(12) 0.0138(10) C(15) 0.0341(12) 0.0310(12) 0.0411(13) 0.0089(10) 0.0139(10) 0.0140(10) C(16) 0.0340(12) 0.0280(12) 0.0443(13) 0.0069(9) 0.0157(11) 0.0096(10) C(17) 0.0342(13) 0.0288(12) 0.0534(15) 0.0086(10) 0.0174(11) 0.0117(11) C(18) 0.0380(14) 0.0374(14) 0.0553(16) 0.0086(11) 0.0166(12) 0.0199(12) C(19) 0.0436(14) 0.0328(13) 0.0488(15) 0.0092(11) 0.0187(12) 0.0184(11) C(20) 0.0387(13) 0.0348(13) 0.0537(15) 0.0111(11) 0.0214(12) 0.0228(12) C(21) 0.0408(14) 0.0326(13) 0.0557(16) 0.0112(11) 0.0199(12) 0.0208(12) C(22) 0.0397(14) 0.0336(13) 0.0527(15) 0.0108(11) 0.0174(12) 0.0193(11) C(23) 0.0380(13) 0.0350(13) 0.0617(17) 0.0122(11) 0.0189(12) 0.0248(12) C(24) 0.0290(12) 0.0329(12) 0.0539(15) 0.0076(10) 0.0153(11) 0.0181(11) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(17) 1.254(3) yes . . O(2) C(17) 1.250(3) yes . . O(3) C(24) 1.250(4) yes . . O(4) C(24) 1.265(4) yes . . N(1) C(15) 1.307(4) yes . . N(2) C(15) 1.302(4) yes . . N(3) C(16) 1.306(4) yes . . N(4) C(16) 1.300(4) yes . . C(1) C(2) 1.362(2) yes . . C(1) C(13) 1.433(4) yes . . C(1) C(15) 1.502(4) yes . . C(2) C(3) 1.427(4) yes . . C(3) C(4) 1.356(4) yes . . C(4) C(14) 1.424(2) yes . . C(5) C(6) 1.356(3) yes . . C(5) C(12) 1.424(4) yes . . C(6) C(7) 1.424(4) yes . . C(7) C(8) 1.362(4) yes . . C(8) C(11) 1.438(2) yes . . C(8) C(16) 1.498(3) yes . . C(9) C(11) 1.391(4) yes . . C(9) C(13) 1.398(2) yes . . C(10) C(12) 1.401(2) yes . . C(10) C(14) 1.396(4) yes . . C(11) C(12) 1.441(4) yes . . C(13) C(14) 1.437(3) yes . . C(17) C(18) 1.524(4) yes . . C(18) C(19) 1.523(3) yes . . C(19) C(20) 1.516(4) yes . . C(20) C(21) 1.516(3) yes . . C(21) C(22) 1.525(4) yes . . C(22) C(23) 1.524(3) yes . . C(23) C(24) 1.522(4) yes . . N(1) H(21) 0.97(4) no . . N(1) H(22) 0.90(4) no . . N(2) H(23) 0.90(4) no . . N(3) H(25) 0.92(4) no . . N(3) H(26) 0.90(4) no . . N(4) H(27) 0.89(4) no . . N(4) H(28) 0.88(4) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.940 no . . C(10) H(8) 0.940 no . . C(18) H(9) 0.980 no . . C(18) H(10) 0.980 no . . C(19) H(11) 0.980 no . . C(19) H(12) 0.980 no . . C(20) H(13) 0.980 no . . C(20) H(14) 0.980 no . . C(21) H(15) 0.980 no . . C(21) H(16) 0.980 no . . C(22) H(17) 0.980 no . . C(22) H(18) 0.980 no . . C(23) H(19) 0.980 no . . C(23) H(20) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(13) 120.9(2) yes . . . C(2) C(1) C(15) 119.1(2) yes . . . C(13) C(1) C(15) 120.03(18) yes . . . C(1) C(2) C(3) 120.7(2) yes . . . C(2) C(3) C(4) 120.2(2) yes . . . C(3) C(4) C(14) 121.0(2) yes . . . C(6) C(5) C(12) 121.0(2) yes . . . C(5) C(6) C(7) 120.5(3) yes . . . C(6) C(7) C(8) 120.6(2) yes . . . C(7) C(8) C(11) 120.9(2) yes . . . C(7) C(8) C(16) 119.99(19) yes . . . C(11) C(8) C(16) 119.1(2) yes . . . C(11) C(9) C(13) 122.0(2) yes . . . C(12) C(10) C(14) 122.0(2) yes . . . C(8) C(11) C(9) 123.3(2) yes . . . C(8) C(11) C(12) 117.8(2) yes . . . C(9) C(11) C(12) 118.83(18) yes . . . C(5) C(12) C(10) 121.8(2) yes . . . C(5) C(12) C(11) 119.15(19) yes . . . C(10) C(12) C(11) 119.1(2) yes . . . C(1) C(13) C(9) 122.6(2) yes . . . C(1) C(13) C(14) 117.93(18) yes . . . C(9) C(13) C(14) 119.4(2) yes . . . C(4) C(14) C(10) 122.1(2) yes . . . C(4) C(14) C(13) 119.2(2) yes . . . C(10) C(14) C(13) 118.61(18) yes . . . N(1) C(15) N(2) 120.7(2) yes . . . N(1) C(15) C(1) 119.8(2) yes . . . N(2) C(15) C(1) 119.5(2) yes . . . N(3) C(16) N(4) 120.4(2) yes . . . N(3) C(16) C(8) 120.1(2) yes . . . N(4) C(16) C(8) 119.5(2) yes . . . O(1) C(17) O(2) 124.9(3) yes . . . O(1) C(17) C(18) 117.8(2) yes . . . O(2) C(17) C(18) 117.3(2) yes . . . C(17) C(18) C(19) 112.2(2) yes . . . C(18) C(19) C(20) 112.7(2) yes . . . C(19) C(20) C(21) 112.4(2) yes . . . C(20) C(21) C(22) 112.9(2) yes . . . C(21) C(22) C(23) 111.3(2) yes . . . C(22) C(23) C(24) 110.2(2) yes . . . O(3) C(24) O(4) 124.0(3) yes . . . O(3) C(24) C(23) 116.6(3) yes . . . O(4) C(24) C(23) 119.4(2) yes . . . C(15) N(1) H(21) 118(2) no . . . C(15) N(1) H(22) 127(2) no . . . H(21) N(1) H(22) 116(3) no . . . C(15) N(2) H(23) 114(2) no . . . C(15) N(2) H(24) 120(2) no . . . H(23) N(2) H(24) 123(4) no . . . C(16) N(3) H(25) 121(2) no . . . C(16) N(3) H(26) 122(2) no . . . H(25) N(3) H(26) 118(3) no . . . C(16) N(4) H(27) 118(2) no . . . C(16) N(4) H(28) 125(2) no . . . H(27) N(4) H(28) 117(3) no . . . C(1) C(2) H(1) 119.7 no . . . C(3) C(2) H(1) 119.7 no . . . C(2) C(3) H(2) 119.9 no . . . C(4) C(3) H(2) 119.9 no . . . C(3) C(4) H(3) 119.5 no . . . C(14) C(4) H(3) 119.5 no . . . C(6) C(5) H(4) 119.5 no . . . C(12) C(5) H(4) 119.5 no . . . C(5) C(6) H(5) 119.8 no . . . C(7) C(6) H(5) 119.8 no . . . C(6) C(7) H(6) 119.7 no . . . C(8) C(7) H(6) 119.7 no . . . C(11) C(9) H(7) 119.0 no . . . C(13) C(9) H(7) 119.0 no . . . C(12) C(10) H(8) 119.0 no . . . C(14) C(10) H(8) 119.0 no . . . C(17) C(18) H(9) 109.2 no . . . C(17) C(18) H(10) 109.2 no . . . C(19) C(18) H(9) 109.2 no . . . C(19) C(18) H(10) 109.2 no . . . H(9) C(18) H(10) 107.9 no . . . C(18) C(19) H(11) 109.1 no . . . C(18) C(19) H(12) 109.1 no . . . C(20) C(19) H(11) 109.1 no . . . C(20) C(19) H(12) 109.1 no . . . H(11) C(19) H(12) 107.8 no . . . C(19) C(20) H(13) 109.1 no . . . C(19) C(20) H(14) 109.1 no . . . C(21) C(20) H(13) 109.1 no . . . C(21) C(20) H(14) 109.1 no . . . H(13) C(20) H(14) 107.9 no . . . C(20) C(21) H(15) 109.0 no . . . C(20) C(21) H(16) 109.0 no . . . C(22) C(21) H(15) 109.0 no . . . C(22) C(21) H(16) 109.0 no . . . H(15) C(21) H(16) 107.8 no . . . C(21) C(22) H(17) 109.4 no . . . C(21) C(22) H(18) 109.4 no . . . C(23) C(22) H(17) 109.4 no . . . C(23) C(22) H(18) 109.4 no . . . H(17) C(22) H(18) 108.0 no . . . C(22) C(23) H(19) 109.6 no . . . C(22) C(23) H(20) 109.6 no . . . C(24) C(23) H(19) 109.6 no . . . C(24) C(23) H(20) 109.6 no . . . H(19) C(23) H(20) 108.1 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(13) C(9) 177.7(3) ? . . . . C(2) C(1) C(13) C(14) -0.6(5) ? . . . . C(13) C(1) C(2) C(3) 1.7(5) ? . . . . C(2) C(1) C(15) N(1) 113.3(3) ? . . . . C(2) C(1) C(15) N(2) -66.1(4) ? . . . . C(15) C(1) C(2) C(3) -178.9(3) ? . . . . C(13) C(1) C(15) N(1) -67.3(3) ? . . . . C(13) C(1) C(15) N(2) 113.3(3) ? . . . . C(15) C(1) C(13) C(9) -1.7(5) ? . . . . C(15) C(1) C(13) C(14) -180.0(2) ? . . . . C(1) C(2) C(3) C(4) -1.7(5) ? . . . . C(2) C(3) C(4) C(14) 0.5(5) ? . . . . C(3) C(4) C(14) C(10) -178.2(3) ? . . . . C(3) C(4) C(14) C(13) 0.7(5) ? . . . . C(6) C(5) C(12) C(10) -178.6(3) ? . . . . C(6) C(5) C(12) C(11) 2.3(5) ? . . . . C(12) C(5) C(6) C(7) -0.9(5) ? . . . . C(5) C(6) C(7) C(8) -1.7(5) ? . . . . C(6) C(7) C(8) C(11) 2.7(5) ? . . . . C(6) C(7) C(8) C(16) -177.0(3) ? . . . . C(7) C(8) C(11) C(9) 176.2(3) ? . . . . C(7) C(8) C(11) C(12) -1.2(5) ? . . . . C(7) C(8) C(16) N(3) -57.5(4) ? . . . . C(7) C(8) C(16) N(4) 123.0(3) ? . . . . C(11) C(8) C(16) N(3) 122.9(3) ? . . . . C(11) C(8) C(16) N(4) -56.7(4) ? . . . . C(16) C(8) C(11) C(9) -4.1(5) ? . . . . C(16) C(8) C(11) C(12) 178.5(3) ? . . . . C(11) C(9) C(13) C(1) -177.2(3) ? . . . . C(11) C(9) C(13) C(14) 1.1(5) ? . . . . C(13) C(9) C(11) C(8) -179.5(3) ? . . . . C(13) C(9) C(11) C(12) -2.1(5) ? . . . . C(12) C(10) C(14) C(4) 179.0(3) ? . . . . C(12) C(10) C(14) C(13) 0.1(4) ? . . . . C(14) C(10) C(12) C(5) 179.8(3) ? . . . . C(14) C(10) C(12) C(11) -1.1(5) ? . . . . C(8) C(11) C(12) C(5) -1.3(4) ? . . . . C(8) C(11) C(12) C(10) 179.6(3) ? . . . . C(9) C(11) C(12) C(5) -178.8(3) ? . . . . C(9) C(11) C(12) C(10) 2.1(4) ? . . . . C(1) C(13) C(14) C(4) -0.6(4) ? . . . . C(1) C(13) C(14) C(10) 178.3(3) ? . . . . C(9) C(13) C(14) C(4) -179.0(3) ? . . . . C(9) C(13) C(14) C(10) -0.1(3) ? . . . . O(1) C(17) C(18) C(19) -128.4(2) ? . . . . O(2) C(17) C(18) C(19) 51.8(4) ? . . . . C(17) C(18) C(19) C(20) -179.9(2) ? . . . . C(18) C(19) C(20) C(21) -179.7(3) ? . . . . C(19) C(20) C(21) C(22) 179.2(2) ? . . . . C(20) C(21) C(22) C(23) 177.5(2) ? . . . . C(21) C(22) C(23) C(24) 177.1(2) ? . . . . C(22) C(23) C(24) O(3) -82.1(3) ? . . . . C(22) C(23) C(24) O(4) 96.7(3) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) O(5) 2.754(3) ? . . O(1) N(3) 3.519(3) ? . . O(1) N(4) 2.747(3) ? . . O(1) C(6) 3.373(3) ? . 2_665 O(1) C(7) 3.344(3) ? . 2_665 O(1) C(16) 3.549(3) ? . . O(2) N(1) 2.823(3) ? . 2_666 O(2) N(3) 2.777(3) ? . . O(2) N(4) 3.571(3) ? . . O(3) O(6) 2.916(3) ? . 1_434 O(3) N(1) 2.746(3) ? . 2_656 O(3) N(2) 3.594(4) ? . 2_656 O(3) N(3) 2.821(3) ? . 1_545 O(3) C(15) 3.590(3) ? . 2_656 O(4) O(5) 2.952(2) ? . 2_656 O(4) O(6) 2.786(3) ? . 2_666 O(4) N(1) 3.571(3) ? . 2_656 O(4) N(2) 2.893(3) ? . 2_656 O(4) C(23) 3.577(3) ? . 2_545 O(5) O(1) 2.754(3) ? . . O(5) O(4) 2.952(2) ? . 2_656 O(5) N(2) 2.846(4) ? . 2_766 O(6) O(3) 2.916(3) ? . 1_676 O(6) O(4) 2.786(3) ? . 2_666 O(6) N(4) 2.811(4) ? . 2_776 O(6) C(4) 3.556(3) ? . . O(6) C(23) 3.502(4) ? . 2_666 O(6) C(24) 3.485(4) ? . 2_666 N(1) O(2) 2.823(3) ? . 2_666 N(1) O(3) 2.746(3) ? . 2_656 N(1) O(4) 3.571(3) ? . 2_656 N(1) C(24) 3.527(4) ? . 2_656 N(2) O(3) 3.594(4) ? . 2_656 N(2) O(4) 2.893(3) ? . 2_656 N(2) O(5) 2.846(4) ? . 2_766 N(3) O(1) 3.519(3) ? . . N(3) O(2) 2.777(3) ? . . N(3) O(3) 2.821(3) ? . 1_565 N(3) C(17) 3.490(4) ? . . N(4) O(1) 2.747(3) ? . . N(4) O(2) 3.571(3) ? . . N(4) O(6) 2.811(4) ? . 2_776 N(4) C(7) 3.543(3) ? . 2_665 N(4) C(17) 3.519(4) ? . . C(3) C(5) 3.598(5) ? . 2_776 C(3) C(10) 3.485(5) ? . 2_776 C(3) C(12) 3.422(5) ? . 2_776 C(4) O(6) 3.556(3) ? . . C(4) C(10) 3.385(4) ? . 2_776 C(4) C(14) 3.535(4) ? . 2_776 C(5) C(3) 3.598(5) ? . 2_776 C(6) O(1) 3.373(3) ? . 2_665 C(6) C(17) 3.472(4) ? . 2_665 C(7) O(1) 3.344(3) ? . 2_665 C(7) N(4) 3.543(3) ? . 2_665 C(10) C(3) 3.485(5) ? . 2_776 C(10) C(4) 3.385(4) ? . 2_776 C(12) C(3) 3.422(5) ? . 2_776 C(14) C(4) 3.535(4) ? . 2_776 C(14) C(14) 3.476(4) ? . 2_776 C(15) O(3) 3.590(3) ? . 2_656 C(16) O(1) 3.549(3) ? . . C(17) N(3) 3.490(4) ? . . C(17) N(4) 3.519(4) ? . . C(17) C(6) 3.472(4) ? . 2_665 C(23) O(4) 3.577(3) ? . 2_545 C(23) O(6) 3.502(4) ? . 2_666 C(23) C(24) 3.496(2) ? . 2_545 C(24) O(6) 3.485(4) ? . 2_666 C(24) N(1) 3.527(4) ? . 2_656 C(24) C(23) 3.496(2) ? . 2_545 C(24) C(24) 3.588(3) ? . 2_545 O(1) H(5) 2.920 ? . 2_665 O(1) H(6) 2.878 ? . 2_665 O(1) H(25) 2.89(4) ? . . O(1) H(27) 1.86(4) ? . . O(1) H(28) 3.24(4) ? . . O(2) H(2) 3.216 ? . 1_444 O(2) H(25) 1.86(4) ? . . O(2) H(26) 3.31(4) ? . . O(2) H(27) 2.92(4) ? . . O(2) H(21) 2.98(4) ? . 2_666 O(2) H(22) 2.07(4) ? . 2_666 O(3) H(19) 3.143 ? . 2_545 O(3) H(20) 3.552 ? . 2_545 O(3) H(25) 2.89(4) ? . 1_545 O(3) H(26) 2.13(4) ? . 1_545 O(3) H(23) 2.91(4) ? . 2_656 O(3) H(21) 1.79(4) ? . 2_656 O(3) H(22) 3.20(3) ? . 2_656 O(4) H(19) 3.564 ? . 2_545 O(4) H(20) 2.908 ? . 2_545 O(4) H(23) 1.99(4) ? . 2_656 O(4) H(21) 2.83(4) ? . 2_656 O(4) H(24) 3.42(4) ? . 2_656 O(5) H(4) 3.214 ? . 1_545 O(5) H(8) 2.704 ? . 1_545 O(5) H(10) 2.925 ? . . O(5) H(18) 3.046 ? . 2_656 O(5) H(23) 3.29(4) ? . 2_766 O(5) H(24) 2.00(4) ? . 2_766 O(6) H(2) 3.588 ? . . O(6) H(3) 2.699 ? . . O(6) H(19) 2.731 ? . 2_666 O(6) H(20) 3.138 ? . 1_676 O(6) H(26) 3.43(2) ? . 1_666 O(6) H(27) 3.28(4) ? . 2_776 O(6) H(28) 1.95(4) ? . 2_776 N(1) H(2) 3.144 ? . 2_777 N(1) H(11) 3.327 ? . 2_666 N(1) H(25) 3.42(4) ? . 2_666 N(1) H(24) 3.04(4) ? . . N(2) H(15) 3.448 ? . 1_666 N(2) H(20) 3.129 ? . 1_666 N(2) H(24) 0.87(4) ? . . N(3) H(9) 3.527 ? . 2_666 N(3) H(17) 3.360 ? . 1_565 N(3) H(21) 3.44(4) ? . 2_666 N(4) H(6) 2.778 ? . 2_665 C(1) H(8) 3.594 ? . 2_776 C(1) H(11) 3.443 ? . 2_666 C(1) H(24) 2.55(4) ? . . C(2) H(8) 3.518 ? . 2_776 C(2) H(11) 3.399 ? . 1_666 C(2) H(16) 3.362 ? . 1_666 C(2) H(24) 3.04(3) ? . . C(3) H(8) 3.564 ? . 2_776 C(3) H(11) 3.558 ? . 1_666 C(3) H(16) 3.352 ? . 2_666 C(3) H(22) 3.47(2) ? . 2_777 C(4) H(16) 2.921 ? . 2_666 C(4) H(18) 3.517 ? . 2_666 C(4) H(19) 3.304 ? . 2_666 C(5) H(2) 3.372 ? . 2_776 C(5) H(10) 3.370 ? . 1_565 C(5) H(12) 3.503 ? . 1_565 C(5) H(12) 3.361 ? . 2_665 C(5) H(14) 2.901 ? . 1_565 C(6) H(12) 3.388 ? . 1_565 C(6) H(12) 3.209 ? . 2_665 C(6) H(14) 2.953 ? . 1_565 C(6) H(15) 3.133 ? . 1_565 C(7) H(14) 3.485 ? . 1_565 C(7) H(15) 3.392 ? . 1_565 C(7) H(17) 3.123 ? . 1_565 C(7) H(27) 3.21(3) ? . 2_665 C(8) H(9) 3.435 ? . 2_666 C(8) H(17) 3.401 ? . 1_565 C(9) H(9) 3.249 ? . 2_666 C(9) H(11) 3.435 ? . 2_666 C(9) H(13) 3.389 ? . 2_666 C(10) H(13) 2.861 ? . 2_666 C(10) H(16) 3.532 ? . 2_666 C(10) H(18) 2.985 ? . 2_666 C(11) H(9) 3.270 ? . 2_666 C(11) H(13) 3.219 ? . 2_666 C(12) H(2) 3.392 ? . 2_776 C(12) H(13) 2.918 ? . 2_666 C(12) H(14) 3.379 ? . 1_565 C(13) H(11) 3.216 ? . 2_666 C(13) H(13) 3.354 ? . 2_666 C(13) H(16) 3.542 ? . 2_666 C(13) H(24) 3.53(4) ? . . C(14) H(13) 3.094 ? . 2_666 C(14) H(16) 3.019 ? . 2_666 C(14) H(18) 3.417 ? . 2_666 C(15) H(24) 1.89(4) ? . . C(16) H(6) 3.564 ? . 2_665 C(17) H(5) 3.098 ? . 2_665 C(17) H(6) 3.509 ? . 2_665 C(17) H(25) 2.65(4) ? . . C(17) H(27) 2.69(4) ? . . C(17) H(22) 3.10(4) ? . 2_666 C(18) H(5) 3.573 ? . 2_665 C(18) H(17) 3.405 ? . 2_656 C(18) H(18) 3.534 ? . 2_656 C(18) H(22) 3.47(3) ? . 2_666 C(19) H(1) 3.215 ? . 1_444 C(19) H(5) 3.544 ? . 2_665 C(19) H(22) 3.35(4) ? . 2_666 C(20) H(13) 3.580 ? . 2_656 C(20) H(14) 3.352 ? . 2_656 C(21) H(1) 3.029 ? . 1_444 C(22) H(8) 3.518 ? . 2_666 C(22) H(9) 3.572 ? . 2_656 C(22) H(10) 3.367 ? . 2_656 C(22) H(26) 3.35(4) ? . 1_545 C(23) H(3) 3.559 ? . 2_666 C(23) H(26) 3.44(4) ? . 1_545 C(23) H(23) 3.47(3) ? . 1_444 C(24) H(19) 3.268 ? . 2_545 C(24) H(20) 3.147 ? . 2_545 C(24) H(26) 3.04(4) ? . 1_545 C(24) H(23) 2.75(4) ? . 2_656 C(24) H(21) 2.60(4) ? . 2_656 H(1) C(19) 3.215 ? . 1_666 H(1) C(21) 3.029 ? . 1_666 H(1) H(4) 3.455 ? . 2_776 H(1) H(11) 2.700 ? . 1_666 H(1) H(12) 2.968 ? . 1_666 H(1) H(15) 2.758 ? . 1_666 H(1) H(16) 2.482 ? . 1_666 H(1) H(24) 2.946 ? . . H(2) O(2) 3.216 ? . 1_666 H(2) O(6) 3.588 ? . . H(2) N(1) 3.144 ? . 2_777 H(2) C(5) 3.372 ? . 2_776 H(2) C(12) 3.392 ? . 2_776 H(2) H(4) 3.568 ? . 2_776 H(2) H(11) 3.017 ? . 1_666 H(2) H(12) 3.473 ? . 1_666 H(2) H(21) 3.481 ? . 2_777 H(2) H(22) 2.728 ? . 2_777 H(3) O(6) 2.699 ? . . H(3) C(23) 3.559 ? . 2_666 H(3) H(16) 3.127 ? . 2_666 H(3) H(18) 3.204 ? . 2_666 H(3) H(19) 2.776 ? . 2_666 H(4) O(5) 3.214 ? . 1_565 H(4) H(1) 3.455 ? . 2_776 H(4) H(2) 3.568 ? . 2_776 H(4) H(5) 3.187 ? . 2_675 H(4) H(10) 2.862 ? . 1_565 H(4) H(12) 3.196 ? . 1_565 H(4) H(12) 3.038 ? . 2_665 H(4) H(14) 3.118 ? . 1_565 H(5) O(1) 2.920 ? . 2_665 H(5) C(17) 3.098 ? . 2_665 H(5) C(18) 3.573 ? . 2_665 H(5) C(19) 3.544 ? . 2_665 H(5) H(4) 3.187 ? . 2_675 H(5) H(5) 3.520 ? . 2_675 H(5) H(10) 3.506 ? . 2_665 H(5) H(12) 2.972 ? . 1_565 H(5) H(12) 2.761 ? . 2_665 H(5) H(14) 3.189 ? . 1_565 H(5) H(15) 2.849 ? . 1_565 H(6) O(1) 2.878 ? . 2_665 H(6) N(4) 2.778 ? . 2_665 H(6) C(16) 3.564 ? . 2_665 H(6) C(17) 3.509 ? . 2_665 H(6) H(15) 3.285 ? . 1_565 H(6) H(17) 3.117 ? . 1_565 H(6) H(20) 3.486 ? . 1_565 H(6) H(25) 3.583 ? . 2_665 H(6) H(27) 2.477 ? . 2_665 H(6) H(28) 2.920 ? . 2_665 H(7) H(9) 3.257 ? . 2_666 H(8) O(5) 2.704 ? . 1_565 H(8) C(1) 3.594 ? . 2_776 H(8) C(2) 3.518 ? . 2_776 H(8) C(3) 3.564 ? . 2_776 H(8) C(22) 3.518 ? . 2_666 H(8) H(10) 3.567 ? . 1_565 H(8) H(13) 3.254 ? . 2_666 H(8) H(18) 2.608 ? . 2_666 H(8) H(24) 3.449 ? . 2_776 H(9) N(3) 3.527 ? . 2_666 H(9) C(8) 3.435 ? . 2_666 H(9) C(9) 3.249 ? . 2_666 H(9) C(11) 3.270 ? . 2_666 H(9) C(22) 3.572 ? . 2_656 H(9) H(7) 3.257 ? . 2_666 H(9) H(14) 3.596 ? . 2_656 H(9) H(17) 2.843 ? . 2_656 H(9) H(18) 3.401 ? . 2_656 H(9) H(26) 3.223 ? . 2_666 H(9) H(22) 3.409 ? . 2_666 H(10) O(5) 2.925 ? . . H(10) C(5) 3.370 ? . 1_545 H(10) C(22) 3.367 ? . 2_656 H(10) H(4) 2.862 ? . 1_545 H(10) H(5) 3.506 ? . 2_665 H(10) H(8) 3.567 ? . 1_545 H(10) H(17) 3.040 ? . 2_656 H(10) H(18) 2.776 ? . 2_656 H(11) N(1) 3.327 ? . 2_666 H(11) C(1) 3.443 ? . 2_666 H(11) C(2) 3.399 ? . 1_444 H(11) C(3) 3.558 ? . 1_444 H(11) C(9) 3.435 ? . 2_666 H(11) C(13) 3.216 ? . 2_666 H(11) H(1) 2.700 ? . 1_444 H(11) H(2) 3.017 ? . 1_444 H(11) H(22) 2.528 ? . 2_666 H(12) C(5) 3.503 ? . 1_545 H(12) C(5) 3.361 ? . 2_665 H(12) C(6) 3.388 ? . 1_545 H(12) C(6) 3.209 ? . 2_665 H(12) H(1) 2.968 ? . 1_444 H(12) H(2) 3.473 ? . 1_444 H(12) H(4) 3.196 ? . 1_545 H(12) H(4) 3.038 ? . 2_665 H(12) H(5) 2.972 ? . 1_545 H(12) H(5) 2.761 ? . 2_665 H(13) C(9) 3.389 ? . 2_666 H(13) C(10) 2.861 ? . 2_666 H(13) C(11) 3.219 ? . 2_666 H(13) C(12) 2.918 ? . 2_666 H(13) C(13) 3.354 ? . 2_666 H(13) C(14) 3.094 ? . 2_666 H(13) C(20) 3.580 ? . 2_656 H(13) H(8) 3.254 ? . 2_666 H(13) H(13) 3.462 ? . 2_656 H(13) H(14) 2.809 ? . 2_656 H(14) C(5) 2.901 ? . 1_545 H(14) C(6) 2.953 ? . 1_545 H(14) C(7) 3.485 ? . 1_545 H(14) C(12) 3.379 ? . 1_545 H(14) C(20) 3.352 ? . 2_656 H(14) H(4) 3.118 ? . 1_545 H(14) H(5) 3.189 ? . 1_545 H(14) H(9) 3.596 ? . 2_656 H(14) H(13) 2.809 ? . 2_656 H(14) H(14) 2.969 ? . 2_656 H(15) N(2) 3.448 ? . 1_444 H(15) C(6) 3.133 ? . 1_545 H(15) C(7) 3.392 ? . 1_545 H(15) H(1) 2.758 ? . 1_444 H(15) H(5) 2.849 ? . 1_545 H(15) H(6) 3.285 ? . 1_545 H(15) H(24) 3.435 ? . 1_444 H(16) C(2) 3.362 ? . 1_444 H(16) C(3) 3.352 ? . 2_666 H(16) C(4) 2.921 ? . 2_666 H(16) C(10) 3.532 ? . 2_666 H(16) C(13) 3.542 ? . 2_666 H(16) C(14) 3.019 ? . 2_666 H(16) H(1) 2.482 ? . 1_444 H(16) H(3) 3.127 ? . 2_666 H(17) N(3) 3.360 ? . 1_545 H(17) C(7) 3.123 ? . 1_545 H(17) C(8) 3.401 ? . 1_545 H(17) C(18) 3.405 ? . 2_656 H(17) H(6) 3.117 ? . 1_545 H(17) H(9) 2.843 ? . 2_656 H(17) H(10) 3.040 ? . 2_656 H(17) H(26) 2.541 ? . 1_545 H(18) O(5) 3.046 ? . 2_656 H(18) C(4) 3.517 ? . 2_666 H(18) C(10) 2.985 ? . 2_666 H(18) C(14) 3.417 ? . 2_666 H(18) C(18) 3.534 ? . 2_656 H(18) H(3) 3.204 ? . 2_666 H(18) H(8) 2.608 ? . 2_666 H(18) H(9) 3.401 ? . 2_656 H(18) H(10) 2.776 ? . 2_656 H(19) O(3) 3.143 ? . 2_545 H(19) O(4) 3.564 ? . 2_545 H(19) O(6) 2.731 ? . 2_666 H(19) C(4) 3.304 ? . 2_666 H(19) C(24) 3.268 ? . 2_545 H(19) H(3) 2.776 ? . 2_666 H(19) H(23) 3.317 ? . 1_444 H(19) H(21) 3.261 ? . 1_444 H(20) O(3) 3.552 ? . 2_545 H(20) O(4) 2.908 ? . 2_545 H(20) O(6) 3.138 ? . 1_434 H(20) N(2) 3.129 ? . 1_444 H(20) C(24) 3.147 ? . 2_545 H(20) H(6) 3.486 ? . 1_545 H(20) H(26) 3.371 ? . 1_545 H(20) H(23) 2.736 ? . 1_444 H(20) H(24) 3.522 ? . 1_444 H(25) O(1) 2.89(4) ? . . H(25) O(2) 1.86(4) ? . . H(25) O(3) 2.89(4) ? . 1_565 H(25) N(1) 3.42(4) ? . 2_666 H(25) C(17) 2.65(4) ? . . H(25) H(6) 3.583 ? . 2_665 H(25) H(21) 3.00(6) ? . 2_666 H(25) H(22) 3.06(5) ? . 2_666 H(26) O(2) 3.31(4) ? . . H(26) O(3) 2.13(4) ? . 1_565 H(26) O(6) 3.43(2) ? . 1_444 H(26) C(22) 3.35(4) ? . 1_565 H(26) C(23) 3.44(4) ? . 1_565 H(26) C(24) 3.04(4) ? . 1_565 H(26) H(9) 3.223 ? . 2_666 H(26) H(17) 2.541 ? . 1_565 H(26) H(20) 3.371 ? . 1_565 H(26) H(21) 3.13(5) ? . 2_666 H(27) O(1) 1.86(4) ? . . H(27) O(2) 2.92(4) ? . . H(27) O(6) 3.28(4) ? . 2_776 H(27) C(7) 3.21(3) ? . 2_665 H(27) C(17) 2.69(4) ? . . H(27) H(6) 2.477 ? . 2_665 H(28) O(1) 3.24(4) ? . . H(28) O(6) 1.95(4) ? . 2_776 H(28) H(6) 2.920 ? . 2_665 H(23) O(3) 2.91(4) ? . 2_656 H(23) O(4) 1.99(4) ? . 2_656 H(23) O(5) 3.29(4) ? . 2_766 H(23) C(23) 3.47(3) ? . 1_666 H(23) C(24) 2.75(4) ? . 2_656 H(23) H(19) 3.317 ? . 1_666 H(23) H(20) 2.736 ? . 1_666 H(23) H(24) 1.55(6) ? . . H(21) O(2) 2.98(4) ? . 2_666 H(21) O(3) 1.79(4) ? . 2_656 H(21) O(4) 2.83(4) ? . 2_656 H(21) N(3) 3.44(4) ? . 2_666 H(21) C(24) 2.60(4) ? . 2_656 H(21) H(2) 3.481 ? . 2_777 H(21) H(19) 3.261 ? . 1_666 H(21) H(25) 3.00(6) ? . 2_666 H(21) H(26) 3.13(5) ? . 2_666 H(21) H(24) 3.29(6) ? . . H(22) O(2) 2.07(4) ? . 2_666 H(22) O(3) 3.20(3) ? . 2_656 H(22) C(3) 3.47(2) ? . 2_777 H(22) C(17) 3.10(4) ? . 2_666 H(22) C(18) 3.47(3) ? . 2_666 H(22) C(19) 3.35(4) ? . 2_666 H(22) H(2) 2.728 ? . 2_777 H(22) H(9) 3.409 ? . 2_666 H(22) H(11) 2.528 ? . 2_666 H(22) H(25) 3.06(5) ? . 2_666 H(24) O(4) 3.42(4) ? . 2_656 H(24) O(5) 2.00(4) ? . 2_766 H(24) N(1) 3.04(4) ? . . H(24) N(2) 0.87(4) ? . . H(24) C(1) 2.55(4) ? . . H(24) C(2) 3.04(3) ? . . H(24) C(13) 3.53(4) ? . . H(24) C(15) 1.89(4) ? . . H(24) H(1) 2.946 ? . . H(24) H(8) 3.449 ? . 2_776 H(24) H(15) 3.435 ? . 1_666 H(24) H(20) 3.522 ? . 1_666 H(24) H(23) 1.55(6) ? . . H(24) H(21) 3.29(6) ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__kusu142 _database_code_depnum_ccdc_archive 'CCDC 920485' #TrackingRef '16988_web_deposit_cif_file_0_TakahiroKusukawa_1358507011.1c2_3c2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C26 H32 N4 O4 ' _chemical_formula_moiety 'C26 H32 N4 O4 ' _chemical_formula_weight 464.56 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 9.7411(15) _cell_length_b 16.079(3) _cell_length_c 7.9526(19) _cell_angle_alpha 98.725(16) _cell_angle_beta 103.439(15) _cell_angle_gamma 79.976(12) _cell_volume 1184.9(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 15 _cell_measurement_theta_min 25.2 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496.00 _exptl_absorpt_coefficient_mu 0.721 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_T_max 0.866 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 213 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 5824 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_theta_max 66.75 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 66.75 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4209 _reflns_number_gt 1805 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1458 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4209 _refine_ls_number_parameters 340 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.23 _refine_diff_density_min -0.23 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 1.0168(2) 0.88435(14) 0.7444(3) 0.0409(6) Uani 1.00 1 d . . . O(2) O 0.7863(2) 0.89504(15) 0.7369(3) 0.0477(7) Uani 1.00 1 d . . . O(3) O 1.4313(2) 0.09597(14) 0.6868(3) 0.0444(7) Uani 1.00 1 d . . . O(4) O 1.2223(2) 0.11569(14) 0.7642(3) 0.0455(7) Uani 1.00 1 d . . . N(1) N 0.4859(3) 1.06063(19) 1.2000(4) 0.0368(7) Uani 1.00 1 d . . . N(2) N 0.7172(2) 1.06199(18) 1.1918(3) 0.0330(7) Uani 1.00 1 d . . . N(3) N 0.7118(3) 1.05335(18) 0.6312(4) 0.0322(6) Uani 1.00 1 d . . . N(4) N 0.9492(3) 1.06141(19) 0.6847(4) 0.0377(7) Uani 1.00 1 d . . . C(1) C 0.5526(3) 1.1957(2) 1.1818(4) 0.0291(7) Uani 1.00 1 d . . . C(2) C 0.4765(3) 1.2414(2) 1.2971(4) 0.0357(8) Uani 1.00 1 d . . . C(3) C 0.4417(3) 1.3311(2) 1.3035(5) 0.0445(10) Uani 1.00 1 d . . . C(4) C 0.4826(3) 1.3723(2) 1.1912(4) 0.0401(9) Uani 1.00 1 d . . . C(5) C 0.7175(3) 1.3696(2) 0.7036(4) 0.0377(9) Uani 1.00 1 d . . . C(6) C 0.7920(3) 1.3263(2) 0.5866(4) 0.0381(8) Uani 1.00 1 d . . . C(7) C 0.8265(3) 1.2363(2) 0.5756(4) 0.0335(8) Uani 1.00 1 d . . . C(8) C 0.7843(3) 1.19274(19) 0.6828(4) 0.0263(7) Uani 1.00 1 d . . . C(9) C 0.6696(3) 1.19424(19) 0.9331(4) 0.0270(7) Uani 1.00 1 d . . . C(10) C 0.5996(3) 1.3696(2) 0.9475(4) 0.0328(8) Uani 1.00 1 d . . . C(11) C 0.5965(3) 1.23728(19) 1.0597(4) 0.0261(7) Uani 1.00 1 d . . . C(12) C 0.5596(3) 1.3276(2) 1.0652(4) 0.0308(8) Uani 1.00 1 d . . . C(13) C 0.7074(3) 1.23583(18) 0.8132(4) 0.0246(7) Uani 1.00 1 d . . . C(14) C 0.6730(3) 1.32674(19) 0.8224(4) 0.0295(7) Uani 1.00 1 d . . . C(15) C 0.5867(3) 1.1024(2) 1.1900(4) 0.0271(7) Uani 1.00 1 d . . . C(16) C 0.8167(3) 1.09823(19) 0.6655(4) 0.0260(7) Uani 1.00 1 d . . . C(17) C 0.9117(3) 0.8590(2) 0.7774(4) 0.0309(8) Uani 1.00 1 d . . . C(18) C 0.9342(3) 0.7784(2) 0.8625(4) 0.0363(8) Uani 1.00 1 d . . . C(19) C 1.0183(3) 0.70425(19) 0.7722(4) 0.0323(8) Uani 1.00 1 d . . . C(20) C 1.0196(3) 0.6190(2) 0.8360(4) 0.0360(8) Uani 1.00 1 d . . . C(21) C 1.1076(3) 0.5454(2) 0.7458(4) 0.0372(8) Uani 1.00 1 d . . . C(22) C 1.1138(3) 0.4597(2) 0.8089(5) 0.0417(9) Uani 1.00 1 d . . . C(23) C 1.2012(3) 0.38746(19) 0.7150(4) 0.0353(8) Uani 1.00 1 d . . . C(24) C 1.2076(3) 0.2993(2) 0.7688(4) 0.0364(8) Uani 1.00 1 d . . . C(25) C 1.2958(3) 0.23219(19) 0.6676(4) 0.0339(8) Uani 1.00 1 d . . . C(26) C 1.3161(3) 0.1416(2) 0.7104(4) 0.0314(8) Uani 1.00 1 d . . . H(1) H 0.4464 1.2129 1.3741 0.043 Uiso 1.00 1 c R . . H(2) H 0.3905 1.3617 1.3853 0.053 Uiso 1.00 1 c R . . H(3) H 0.4597 1.4318 1.1967 0.048 Uiso 1.00 1 c R . . H(4) H 0.6945 1.4290 0.7073 0.045 Uiso 1.00 1 c R . . H(5) H 0.8215 1.3560 0.5113 0.046 Uiso 1.00 1 c R . . H(6) H 0.8787 1.2069 0.4936 0.040 Uiso 1.00 1 c R . . H(7) H 0.6941 1.1349 0.9287 0.032 Uiso 1.00 1 c R . . H(8) H 0.5761 1.4290 0.9529 0.039 Uiso 1.00 1 c R . . H(9) H 0.9846 0.7890 0.9839 0.044 Uiso 1.00 1 c R . . H(10) H 0.8410 0.7633 0.8629 0.044 Uiso 1.00 1 c R . . H(11) H 1.1169 0.7152 0.7902 0.039 Uiso 1.00 1 c R . . H(12) H 0.9778 0.7003 0.6468 0.039 Uiso 1.00 1 c R . . H(13) H 1.0584 0.6230 0.9617 0.043 Uiso 1.00 1 c R . . H(14) H 0.9213 0.6071 0.8155 0.043 Uiso 1.00 1 c R . . H(15) H 1.0674 0.5411 0.6204 0.045 Uiso 1.00 1 c R . . H(16) H 1.2051 0.5583 0.7640 0.045 Uiso 1.00 1 c R . . H(17) H 1.0165 0.4467 0.7916 0.050 Uiso 1.00 1 c R . . H(18) H 1.1554 0.4635 0.9340 0.050 Uiso 1.00 1 c R . . H(19) H 1.2988 0.4003 0.7352 0.042 Uiso 1.00 1 c R . . H(20) H 1.1612 0.3857 0.5897 0.042 Uiso 1.00 1 c R . . H(21) H 1.2493 0.2998 0.8935 0.044 Uiso 1.00 1 c R . . H(22) H 1.1107 0.2853 0.7483 0.044 Uiso 1.00 1 c R . . H(23) H 1.3904 0.2492 0.6848 0.041 Uiso 1.00 1 c R . . H(24) H 1.2516 0.2325 0.5436 0.041 Uiso 1.00 1 c R . . H(25) H 0.793(3) 1.095(2) 1.192(4) 0.051(11) Uiso 1.00 1 c . . . H(26) H 0.734(3) 0.999(2) 1.202(4) 0.050(10) Uiso 1.00 1 c . . . H(27) H 0.514(3) 1.001(2) 1.222(4) 0.050(11) Uiso 1.00 1 c . . . H(28) H 0.396(4) 1.091(2) 1.203(5) 0.072(13) Uiso 1.00 1 c . . . H(29) H 0.623(3) 1.081(2) 0.638(4) 0.037(10) Uiso 1.00 1 c . . . H(30) H 0.731(3) 0.993(2) 0.643(4) 0.044(10) Uiso 1.00 1 c . . . H(31) H 0.971(3) 1.000(2) 0.688(4) 0.055(11) Uiso 1.00 1 c . . . H(32) H 1.032(3) 1.095(2) 0.716(4) 0.046(10) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0276(13) 0.0322(13) 0.0688(19) -0.0057(10) 0.0157(12) 0.0141(12) O(2) 0.0273(13) 0.0389(14) 0.083(2) 0.0051(10) 0.0182(13) 0.0256(14) O(3) 0.0306(13) 0.0291(13) 0.077(2) 0.0040(10) 0.0194(13) 0.0133(13) O(4) 0.0345(14) 0.0326(13) 0.077(2) -0.0028(10) 0.0229(13) 0.0160(13) N(1) 0.0271(16) 0.0294(16) 0.060(2) -0.0015(12) 0.0174(15) 0.0147(15) N(2) 0.0267(16) 0.0273(16) 0.050(2) 0.0010(12) 0.0150(14) 0.0135(15) N(3) 0.0321(16) 0.0199(14) 0.048(2) -0.0009(12) 0.0165(14) 0.0043(13) N(4) 0.0261(16) 0.0242(16) 0.065(2) 0.0006(12) 0.0163(15) 0.0075(15) C(1) 0.0280(17) 0.0238(17) 0.036(2) -0.0009(13) 0.0094(15) 0.0030(15) C(2) 0.0325(19) 0.039(2) 0.040(2) -0.0018(15) 0.0177(17) 0.0064(17) C(3) 0.051(2) 0.037(2) 0.050(2) 0.0034(18) 0.029(2) 0.0015(19) C(4) 0.044(2) 0.0266(19) 0.050(2) 0.0022(16) 0.0191(19) -0.0007(18) C(5) 0.048(2) 0.0250(18) 0.045(2) -0.0031(16) 0.0187(19) 0.0104(17) C(6) 0.050(2) 0.0314(18) 0.042(2) -0.0061(16) 0.0218(18) 0.0118(17) C(7) 0.0354(19) 0.0277(18) 0.040(2) -0.0029(14) 0.0156(16) 0.0036(16) C(8) 0.0245(16) 0.0239(16) 0.033(2) -0.0035(12) 0.0105(15) 0.0045(15) C(9) 0.0266(17) 0.0189(15) 0.035(2) -0.0006(13) 0.0059(15) 0.0040(14) C(10) 0.0376(19) 0.0179(15) 0.044(2) 0.0049(13) 0.0155(16) 0.0050(15) C(11) 0.0265(17) 0.0242(16) 0.029(2) -0.0007(13) 0.0088(15) 0.0045(15) C(12) 0.0287(17) 0.0267(17) 0.036(2) 0.0014(14) 0.0077(15) 0.0040(16) C(13) 0.0234(16) 0.0194(15) 0.0302(19) -0.0008(12) 0.0050(14) 0.0040(14) C(14) 0.0285(17) 0.0224(17) 0.038(2) -0.0028(13) 0.0067(15) 0.0046(15) C(15) 0.0240(17) 0.0317(18) 0.0273(19) -0.0032(13) 0.0068(14) 0.0075(15) C(16) 0.0301(17) 0.0205(16) 0.031(2) 0.0012(13) 0.0143(15) 0.0066(14) C(17) 0.0268(18) 0.0202(16) 0.046(2) 0.0001(13) 0.0111(16) 0.0037(15) C(18) 0.0358(19) 0.0290(19) 0.047(2) -0.0021(15) 0.0146(17) 0.0082(17) C(19) 0.0358(19) 0.0217(17) 0.040(2) 0.0017(14) 0.0111(16) 0.0081(15) C(20) 0.0362(19) 0.0288(19) 0.044(2) -0.0032(15) 0.0104(17) 0.0069(17) C(21) 0.042(2) 0.0267(18) 0.044(2) -0.0034(15) 0.0109(17) 0.0078(16) C(22) 0.044(2) 0.0274(19) 0.056(2) -0.0007(16) 0.0147(19) 0.0095(18) C(23) 0.038(2) 0.0249(18) 0.043(2) -0.0027(15) 0.0085(17) 0.0061(16) C(24) 0.0311(19) 0.0301(19) 0.049(2) 0.0008(14) 0.0140(17) 0.0063(17) C(25) 0.0345(19) 0.0262(18) 0.041(2) 0.0004(14) 0.0098(16) 0.0063(16) C(26) 0.0299(18) 0.0235(17) 0.040(2) -0.0033(14) 0.0067(16) 0.0034(16) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(17) 1.260(4) yes . . O(2) C(17) 1.249(3) yes . . O(3) C(26) 1.266(3) yes . . O(4) C(26) 1.248(4) yes . . N(1) C(15) 1.306(4) yes . . N(2) C(15) 1.321(3) yes . . N(3) C(16) 1.307(4) yes . . N(4) C(16) 1.307(4) yes . . C(1) C(2) 1.361(4) yes . . C(1) C(11) 1.436(5) yes . . C(1) C(15) 1.487(4) yes . . C(2) C(3) 1.419(4) yes . . C(3) C(4) 1.353(6) yes . . C(4) C(12) 1.424(5) yes . . C(5) C(6) 1.349(5) yes . . C(5) C(14) 1.431(5) yes . . C(6) C(7) 1.423(4) yes . . C(7) C(8) 1.352(5) yes . . C(8) C(13) 1.442(4) yes . . C(8) C(16) 1.489(4) yes . . C(9) C(11) 1.396(4) yes . . C(9) C(13) 1.391(5) yes . . C(10) C(12) 1.391(5) yes . . C(10) C(14) 1.388(4) yes . . C(11) C(12) 1.431(4) yes . . C(13) C(14) 1.436(4) yes . . C(17) C(18) 1.511(5) yes . . C(18) C(19) 1.510(4) yes . . C(19) C(20) 1.530(4) yes . . C(20) C(21) 1.525(4) yes . . C(21) C(22) 1.523(5) yes . . C(22) C(23) 1.523(4) yes . . C(23) C(24) 1.529(4) yes . . C(24) C(25) 1.512(4) yes . . C(25) C(26) 1.515(4) yes . . N(1) H(27) 0.98(3) no . . N(2) H(25) 0.98(4) no . . N(2) H(26) 1.01(3) no . . N(3) H(29) 0.91(3) no . . N(3) H(30) 0.97(3) no . . N(4) H(31) 0.97(3) no . . N(4) H(32) 1.01(3) no . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.940 no . . C(5) H(4) 0.940 no . . C(6) H(5) 0.940 no . . C(7) H(6) 0.940 no . . C(9) H(7) 0.940 no . . C(10) H(8) 0.940 no . . C(18) H(9) 0.980 no . . C(18) H(10) 0.980 no . . C(19) H(11) 0.980 no . . C(19) H(12) 0.980 no . . C(20) H(13) 0.980 no . . C(20) H(14) 0.980 no . . C(21) H(15) 0.980 no . . C(21) H(16) 0.980 no . . C(22) H(17) 0.980 no . . C(22) H(18) 0.980 no . . C(23) H(19) 0.980 no . . C(23) H(20) 0.980 no . . C(24) H(21) 0.980 no . . C(24) H(22) 0.980 no . . C(25) H(23) 0.980 no . . C(25) H(24) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(11) 120.5(2) yes . . . C(2) C(1) C(15) 116.7(3) yes . . . C(11) C(1) C(15) 122.8(2) yes . . . C(1) C(2) C(3) 121.2(3) yes . . . C(2) C(3) C(4) 119.7(3) yes . . . C(3) C(4) C(12) 121.5(3) yes . . . C(6) C(5) C(14) 121.1(3) yes . . . C(5) C(6) C(7) 120.8(3) yes . . . C(6) C(7) C(8) 120.2(3) yes . . . C(7) C(8) C(13) 121.4(2) yes . . . C(7) C(8) C(16) 119.5(3) yes . . . C(13) C(8) C(16) 119.0(3) yes . . . C(11) C(9) C(13) 122.5(2) yes . . . C(12) C(10) C(14) 122.3(2) yes . . . C(1) C(11) C(9) 123.7(2) yes . . . C(1) C(11) C(12) 118.1(2) yes . . . C(9) C(11) C(12) 118.3(3) yes . . . C(4) C(12) C(10) 121.7(3) yes . . . C(4) C(12) C(11) 119.0(3) yes . . . C(10) C(12) C(11) 119.4(3) yes . . . C(8) C(13) C(9) 123.4(2) yes . . . C(8) C(13) C(14) 117.8(3) yes . . . C(9) C(13) C(14) 118.8(2) yes . . . C(5) C(14) C(10) 122.6(2) yes . . . C(5) C(14) C(13) 118.6(3) yes . . . C(10) C(14) C(13) 118.7(3) yes . . . N(1) C(15) N(2) 119.9(3) yes . . . N(1) C(15) C(1) 118.9(2) yes . . . N(2) C(15) C(1) 121.2(3) yes . . . N(3) C(16) N(4) 121.0(2) yes . . . N(3) C(16) C(8) 119.3(2) yes . . . N(4) C(16) C(8) 119.7(3) yes . . . O(1) C(17) O(2) 123.5(3) yes . . . O(1) C(17) C(18) 119.5(2) yes . . . O(2) C(17) C(18) 116.9(3) yes . . . C(17) C(18) C(19) 113.1(3) yes . . . C(18) C(19) C(20) 113.7(3) yes . . . C(19) C(20) C(21) 112.8(3) yes . . . C(20) C(21) C(22) 114.3(3) yes . . . C(21) C(22) C(23) 112.9(3) yes . . . C(22) C(23) C(24) 115.4(3) yes . . . C(23) C(24) C(25) 111.3(3) yes . . . C(24) C(25) C(26) 117.5(3) yes . . . O(3) C(26) O(4) 123.8(3) yes . . . O(3) C(26) C(25) 115.7(3) yes . . . O(4) C(26) C(25) 120.4(2) yes . . . C(15) N(1) H(27) 117(2) no . . . C(15) N(1) H(28) 118(2) no . . . H(27) N(1) H(28) 124(3) no . . . C(15) N(2) H(25) 118.7(18) no . . . C(15) N(2) H(26) 117(2) no . . . H(25) N(2) H(26) 124(2) no . . . C(16) N(3) H(29) 118(2) no . . . C(16) N(3) H(30) 120(2) no . . . H(29) N(3) H(30) 118(3) no . . . C(16) N(4) H(31) 119(2) no . . . C(16) N(4) H(32) 122.1(18) no . . . H(31) N(4) H(32) 118(2) no . . . C(1) C(2) H(1) 119.4 no . . . C(3) C(2) H(1) 119.4 no . . . C(2) C(3) H(2) 120.1 no . . . C(4) C(3) H(2) 120.1 no . . . C(3) C(4) H(3) 119.3 no . . . C(12) C(4) H(3) 119.3 no . . . C(6) C(5) H(4) 119.4 no . . . C(14) C(5) H(4) 119.4 no . . . C(5) C(6) H(5) 119.6 no . . . C(7) C(6) H(5) 119.6 no . . . C(6) C(7) H(6) 119.9 no . . . C(8) C(7) H(6) 119.9 no . . . C(11) C(9) H(7) 118.7 no . . . C(13) C(9) H(7) 118.7 no . . . C(12) C(10) H(8) 118.8 no . . . C(14) C(10) H(8) 118.9 no . . . C(17) C(18) H(9) 109.0 no . . . C(17) C(18) H(10) 109.0 no . . . C(19) C(18) H(9) 109.0 no . . . C(19) C(18) H(10) 109.0 no . . . H(9) C(18) H(10) 107.8 no . . . C(18) C(19) H(11) 108.8 no . . . C(18) C(19) H(12) 108.8 no . . . C(20) C(19) H(11) 108.8 no . . . C(20) C(19) H(12) 108.8 no . . . H(11) C(19) H(12) 107.7 no . . . C(19) C(20) H(13) 109.0 no . . . C(19) C(20) H(14) 109.0 no . . . C(21) C(20) H(13) 109.0 no . . . C(21) C(20) H(14) 109.0 no . . . H(13) C(20) H(14) 107.8 no . . . C(20) C(21) H(15) 108.7 no . . . C(20) C(21) H(16) 108.7 no . . . C(22) C(21) H(15) 108.7 no . . . C(22) C(21) H(16) 108.7 no . . . H(15) C(21) H(16) 107.6 no . . . C(21) C(22) H(17) 109.0 no . . . C(21) C(22) H(18) 109.0 no . . . C(23) C(22) H(17) 109.0 no . . . C(23) C(22) H(18) 109.0 no . . . H(17) C(22) H(18) 107.8 no . . . C(22) C(23) H(19) 108.4 no . . . C(22) C(23) H(20) 108.4 no . . . C(24) C(23) H(19) 108.4 no . . . C(24) C(23) H(20) 108.4 no . . . H(19) C(23) H(20) 107.5 no . . . C(23) C(24) H(21) 109.4 no . . . C(23) C(24) H(22) 109.4 no . . . C(25) C(24) H(21) 109.4 no . . . C(25) C(24) H(22) 109.4 no . . . H(21) C(24) H(22) 108.0 no . . . C(24) C(25) H(23) 107.9 no . . . C(24) C(25) H(24) 107.9 no . . . C(26) C(25) H(23) 107.9 no . . . C(26) C(25) H(24) 107.9 no . . . H(23) C(25) H(24) 107.2 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(11) C(9) -177.3(2) ? . . . . C(2) C(1) C(11) C(12) 0.9(4) ? . . . . C(11) C(1) C(2) C(3) -1.7(4) ? . . . . C(2) C(1) C(15) N(1) 46.1(4) ? . . . . C(2) C(1) C(15) N(2) -132.1(3) ? . . . . C(15) C(1) C(2) C(3) 178.2(2) ? . . . . C(11) C(1) C(15) N(1) -133.9(3) ? . . . . C(11) C(1) C(15) N(2) 47.8(4) ? . . . . C(15) C(1) C(11) C(9) 2.8(4) ? . . . . C(15) C(1) C(11) C(12) -179.0(2) ? . . . . C(1) C(2) C(3) C(4) 1.1(4) ? . . . . C(2) C(3) C(4) C(12) 0.4(5) ? . . . . C(3) C(4) C(12) C(10) 178.8(3) ? . . . . C(3) C(4) C(12) C(11) -1.1(4) ? . . . . C(6) C(5) C(14) C(10) 178.2(3) ? . . . . C(6) C(5) C(14) C(13) -0.9(4) ? . . . . C(14) C(5) C(6) C(7) 1.1(4) ? . . . . C(5) C(6) C(7) C(8) 0.2(4) ? . . . . C(6) C(7) C(8) C(13) -1.7(4) ? . . . . C(6) C(7) C(8) C(16) 177.9(2) ? . . . . C(7) C(8) C(13) C(9) -175.9(2) ? . . . . C(7) C(8) C(13) C(14) 1.8(4) ? . . . . C(7) C(8) C(16) N(3) -120.6(3) ? . . . . C(7) C(8) C(16) N(4) 59.4(4) ? . . . . C(13) C(8) C(16) N(3) 58.9(4) ? . . . . C(13) C(8) C(16) N(4) -121.1(3) ? . . . . C(16) C(8) C(13) C(9) 4.5(4) ? . . . . C(16) C(8) C(13) C(14) -177.7(2) ? . . . . C(11) C(9) C(13) C(8) 179.2(2) ? . . . . C(11) C(9) C(13) C(14) 1.5(4) ? . . . . C(13) C(9) C(11) C(1) 178.2(2) ? . . . . C(13) C(9) C(11) C(12) 0.0(4) ? . . . . C(12) C(10) C(14) C(5) -178.5(2) ? . . . . C(12) C(10) C(14) C(13) 0.7(4) ? . . . . C(14) C(10) C(12) C(4) -179.1(2) ? . . . . C(14) C(10) C(12) C(11) 0.8(4) ? . . . . C(1) C(11) C(12) C(4) 0.5(4) ? . . . . C(1) C(11) C(12) C(10) -179.4(2) ? . . . . C(9) C(11) C(12) C(4) 178.8(2) ? . . . . C(9) C(11) C(12) C(10) -1.2(4) ? . . . . C(8) C(13) C(14) C(5) -0.5(4) ? . . . . C(8) C(13) C(14) C(10) -179.7(2) ? . . . . C(9) C(13) C(14) C(5) 177.4(2) ? . . . . C(9) C(13) C(14) C(10) -1.8(4) ? . . . . O(1) C(17) C(18) C(19) -50.3(4) ? . . . . O(2) C(17) C(18) C(19) 126.8(3) ? . . . . C(17) C(18) C(19) C(20) -169.8(2) ? . . . . C(18) C(19) C(20) C(21) -178.8(2) ? . . . . C(19) C(20) C(21) C(22) 178.8(2) ? . . . . C(20) C(21) C(22) C(23) 179.4(2) ? . . . . C(21) C(22) C(23) C(24) -178.2(2) ? . . . . C(22) C(23) C(24) C(25) 179.7(2) ? . . . . C(23) C(24) C(25) C(26) 178.1(2) ? . . . . C(24) C(25) C(26) O(3) -150.4(2) ? . . . . C(24) C(25) C(26) O(4) 30.1(4) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) N(2) 2.784(3) ? . 2_777 O(1) N(4) 2.894(3) ? . . O(1) C(7) 3.442(4) ? . 2_776 O(2) O(3) 3.548(3) ? . 2_766 O(2) N(1) 2.764(4) ? . 2_677 O(2) N(3) 2.727(3) ? . . O(2) N(4) 3.459(4) ? . . O(2) C(2) 3.590(4) ? . 2_677 O(2) C(16) 3.473(4) ? . . O(2) C(25) 3.542(4) ? . 2_766 O(2) C(26) 3.452(4) ? . 2_766 O(3) O(2) 3.548(3) ? . 2_766 O(3) N(1) 2.728(3) ? . 2_767 O(3) N(2) 3.485(4) ? . 2_767 O(3) N(3) 2.820(3) ? . 1_645 O(3) N(3) 3.434(3) ? . 2_766 O(3) C(9) 3.154(3) ? . 1_645 O(3) C(15) 3.519(4) ? . 2_767 O(4) N(2) 2.873(3) ? . 2_767 O(4) N(4) 2.845(3) ? . 1_545 N(1) O(2) 2.764(4) ? . 2_677 N(1) O(3) 2.728(3) ? . 2_767 N(1) N(1) 3.513(4) ? . 2_677 N(1) N(3) 3.470(5) ? . 2_677 N(1) C(26) 3.561(4) ? . 2_767 N(2) O(1) 2.784(3) ? . 2_777 N(2) O(3) 3.485(4) ? . 2_767 N(2) O(4) 2.873(3) ? . 2_767 N(2) N(3) 3.532(4) ? . 1_556 N(2) N(4) 3.510(3) ? . 2_777 N(2) C(26) 3.561(4) ? . 2_767 N(3) O(2) 2.727(3) ? . . N(3) O(3) 2.820(3) ? . 1_465 N(3) O(3) 3.434(3) ? . 2_766 N(3) N(1) 3.470(5) ? . 2_677 N(3) N(2) 3.532(4) ? . 1_554 N(3) C(15) 3.597(4) ? . 1_554 N(3) C(17) 3.584(4) ? . . N(4) O(1) 2.894(3) ? . . N(4) O(2) 3.459(4) ? . . N(4) O(4) 2.845(3) ? . 1_565 N(4) N(2) 3.510(3) ? . 2_777 N(4) N(4) 3.525(4) ? . 2_776 N(4) C(17) 3.541(4) ? . . C(2) O(2) 3.590(4) ? . 2_677 C(7) O(1) 3.442(4) ? . 2_776 C(9) O(3) 3.154(3) ? . 1_465 C(15) O(3) 3.519(4) ? . 2_767 C(15) N(3) 3.597(4) ? . 1_556 C(16) O(2) 3.473(4) ? . . C(17) N(3) 3.584(4) ? . . C(17) N(4) 3.541(4) ? . . C(25) O(2) 3.542(4) ? . 2_766 C(26) O(2) 3.452(4) ? . 2_766 C(26) N(1) 3.561(4) ? . 2_767 C(26) N(2) 3.561(4) ? . 2_767 O(1) H(6) 2.511 ? . 2_776 O(1) H(7) 3.364 ? . 2_777 O(1) H(25) 1.88(3) ? . 2_777 O(1) H(26) 3.23(3) ? . 2_777 O(1) H(30) 3.02(3) ? . . O(1) H(31) 1.94(3) ? . . O(1) H(32) 3.46(3) ? . . O(2) H(1) 2.984 ? . 2_677 O(2) H(24) 2.795 ? . 2_766 O(2) H(27) 3.17(3) ? . 2_677 O(2) H(28) 1.91(4) ? . 2_677 O(2) H(29) 3.25(3) ? . . O(2) H(30) 1.79(3) ? . . O(2) H(31) 2.80(4) ? . . O(3) H(1) 3.381 ? . 1_644 O(3) H(7) 2.924 ? . 1_645 O(3) H(26) 2.77(4) ? . 2_767 O(3) H(27) 1.77(3) ? . 2_767 O(3) H(28) 3.32(3) ? . 2_767 O(3) H(29) 1.97(3) ? . 1_645 O(3) H(29) 3.56(3) ? . 2_766 O(3) H(30) 3.16(3) ? . 1_645 O(3) H(30) 3.02(3) ? . 2_766 O(4) H(9) 3.209 ? . 2_767 O(4) H(10) 3.413 ? . 2_767 O(4) H(25) 3.49(3) ? . 2_767 O(4) H(26) 1.87(3) ? . 2_767 O(4) H(27) 2.89(3) ? . 2_767 O(4) H(28) 3.55(3) ? . 1_645 O(4) H(30) 3.52(3) ? . 2_766 O(4) H(31) 3.22(4) ? . 1_545 O(4) H(32) 1.88(3) ? . 1_545 N(1) H(26) 3.51(3) ? . 2_677 N(1) H(27) 3.35(3) ? . 2_677 N(1) H(28) 0.93(4) ? . . N(1) H(29) 3.41(3) ? . 1_556 N(1) H(29) 3.22(3) ? . 2_677 N(1) H(30) 2.99(4) ? . 2_677 N(2) H(6) 3.390 ? . 1_556 N(2) H(28) 3.11(4) ? . . N(2) H(31) 3.01(3) ? . 2_777 N(2) H(32) 3.23(3) ? . 2_777 N(3) H(26) 3.44(3) ? . 1_554 N(3) H(27) 3.44(3) ? . 1_554 N(3) H(27) 3.03(4) ? . 2_677 N(3) H(28) 3.26(4) ? . 2_677 N(4) H(9) 3.313 ? . 2_777 N(4) H(25) 3.32(3) ? . 2_777 N(4) H(26) 3.03(3) ? . 2_777 N(4) H(31) 3.21(3) ? . 2_776 C(1) H(6) 3.560 ? . 1_556 C(1) H(28) 2.51(4) ? . . C(2) H(10) 3.068 ? . 2_677 C(2) H(23) 3.357 ? . 1_466 C(2) H(24) 3.294 ? . 1_466 C(2) H(28) 2.62(4) ? . . C(3) H(10) 3.285 ? . 2_677 C(3) H(14) 3.449 ? . 2_677 C(3) H(21) 3.374 ? . 1_465 C(4) H(4) 3.432 ? . 2_687 C(4) H(8) 3.467 ? . 2_687 C(4) H(16) 3.345 ? . 2_777 C(4) H(18) 3.570 ? . 1_465 C(4) H(21) 3.117 ? . 1_465 C(5) H(2) 3.588 ? . 1_554 C(5) H(3) 3.428 ? . 2_687 C(5) H(13) 3.026 ? . 2_777 C(5) H(17) 3.249 ? . 1_565 C(6) H(11) 3.262 ? . 2_776 C(6) H(12) 3.165 ? . 2_776 C(6) H(13) 3.575 ? . 2_777 C(6) H(15) 3.502 ? . 2_776 C(6) H(16) 3.584 ? . 2_776 C(6) H(17) 3.170 ? . 1_565 C(6) H(22) 3.068 ? . 1_565 C(7) H(11) 3.311 ? . 2_776 C(7) H(12) 3.255 ? . 2_776 C(7) H(22) 2.972 ? . 1_565 C(7) H(25) 3.50(3) ? . 1_554 C(8) H(9) 3.066 ? . 2_777 C(9) H(9) 3.330 ? . 2_777 C(9) H(11) 3.040 ? . 2_777 C(9) H(23) 3.045 ? . 1_465 C(10) H(3) 3.466 ? . 2_687 C(10) H(8) 3.460 ? . 2_687 C(10) H(11) 3.273 ? . 2_777 C(10) H(13) 3.260 ? . 2_777 C(10) H(16) 2.857 ? . 2_777 C(10) H(19) 3.022 ? . 1_465 C(10) H(23) 3.230 ? . 1_465 C(11) H(11) 2.953 ? . 2_777 C(11) H(21) 3.367 ? . 1_465 C(11) H(23) 3.196 ? . 1_465 C(12) H(11) 3.087 ? . 2_777 C(12) H(16) 3.119 ? . 2_777 C(12) H(19) 3.392 ? . 1_465 C(12) H(21) 3.094 ? . 1_465 C(12) H(23) 3.272 ? . 1_465 C(13) H(9) 3.049 ? . 2_777 C(13) H(11) 3.271 ? . 2_777 C(13) H(13) 3.497 ? . 2_777 C(13) H(23) 2.999 ? . 1_465 C(14) H(11) 3.370 ? . 2_777 C(14) H(13) 2.945 ? . 2_777 C(14) H(16) 3.571 ? . 2_777 C(14) H(19) 3.570 ? . 1_465 C(14) H(23) 3.116 ? . 1_465 C(15) H(27) 3.45(3) ? . 2_677 C(15) H(28) 1.93(4) ? . . C(15) H(29) 3.56(3) ? . 1_556 C(16) H(9) 3.462 ? . 2_777 C(17) H(6) 3.246 ? . 2_776 C(17) H(24) 3.000 ? . 2_766 C(17) H(25) 3.04(3) ? . 2_777 C(17) H(28) 3.00(4) ? . 2_677 C(17) H(30) 2.72(3) ? . . C(17) H(31) 2.67(4) ? . . C(18) H(21) 3.416 ? . 2_767 C(18) H(22) 3.544 ? . 2_767 C(18) H(24) 3.311 ? . 2_766 C(18) H(28) 3.49(3) ? . 2_677 C(19) H(5) 2.984 ? . 2_776 C(19) H(6) 3.149 ? . 2_776 C(19) H(20) 3.272 ? . 2_766 C(19) H(24) 3.322 ? . 2_766 C(20) H(5) 3.568 ? . 2_776 C(20) H(17) 3.402 ? . 2_767 C(20) H(18) 3.314 ? . 2_767 C(20) H(20) 3.430 ? . 2_766 C(21) H(5) 3.032 ? . 2_776 C(21) H(8) 3.480 ? . 2_777 C(21) H(15) 3.257 ? . 2_766 C(21) H(20) 3.441 ? . 2_766 C(22) H(13) 3.293 ? . 2_767 C(22) H(14) 3.431 ? . 2_767 C(22) H(15) 3.459 ? . 2_766 C(23) H(2) 3.478 ? . 1_644 C(23) H(12) 3.256 ? . 2_766 C(23) H(15) 3.452 ? . 2_766 C(24) H(9) 3.588 ? . 2_767 C(24) H(10) 3.394 ? . 2_767 C(24) H(12) 3.379 ? . 2_766 C(25) H(1) 2.985 ? . 1_644 C(25) H(12) 3.354 ? . 2_766 C(26) H(26) 2.62(4) ? . 2_767 C(26) H(27) 2.63(3) ? . 2_767 C(26) H(29) 3.14(3) ? . 1_645 C(26) H(30) 3.27(3) ? . 2_766 C(26) H(32) 3.00(3) ? . 1_545 H(1) O(2) 2.984 ? . 2_677 H(1) O(3) 3.381 ? . 1_466 H(1) C(25) 2.985 ? . 1_466 H(1) H(10) 2.988 ? . 2_677 H(1) H(23) 2.612 ? . 1_466 H(1) H(24) 2.524 ? . 1_466 H(1) H(28) 2.272 ? . . H(1) H(29) 3.204 ? . 1_556 H(2) C(5) 3.588 ? . 1_556 H(2) C(23) 3.478 ? . 1_466 H(2) H(4) 3.470 ? . 2_687 H(2) H(10) 3.365 ? . 2_677 H(2) H(14) 3.079 ? . 2_677 H(2) H(19) 3.060 ? . 1_466 H(2) H(20) 2.996 ? . 1_466 H(2) H(23) 3.202 ? . 1_466 H(2) H(24) 3.209 ? . 1_466 H(3) C(5) 3.428 ? . 2_687 H(3) C(10) 3.466 ? . 2_687 H(3) H(4) 2.587 ? . 2_687 H(3) H(8) 2.625 ? . 2_687 H(3) H(16) 3.237 ? . 2_777 H(3) H(18) 3.214 ? . 1_465 H(3) H(21) 3.490 ? . 1_465 H(4) C(4) 3.432 ? . 2_687 H(4) H(2) 3.470 ? . 2_687 H(4) H(3) 2.587 ? . 2_687 H(4) H(13) 3.232 ? . 2_777 H(4) H(17) 3.106 ? . 1_565 H(4) H(18) 3.272 ? . 2_777 H(5) C(19) 2.984 ? . 2_776 H(5) C(20) 3.568 ? . 2_776 H(5) C(21) 3.032 ? . 2_776 H(5) H(11) 2.650 ? . 2_776 H(5) H(12) 2.531 ? . 2_776 H(5) H(15) 2.585 ? . 2_776 H(5) H(16) 2.700 ? . 2_776 H(5) H(17) 2.952 ? . 1_565 H(5) H(20) 3.326 ? . 1_565 H(5) H(22) 3.138 ? . 1_565 H(6) O(1) 2.511 ? . 2_776 H(6) N(2) 3.390 ? . 1_554 H(6) C(1) 3.560 ? . 1_554 H(6) C(17) 3.246 ? . 2_776 H(6) C(19) 3.149 ? . 2_776 H(6) H(11) 2.754 ? . 2_776 H(6) H(12) 2.717 ? . 2_776 H(6) H(22) 2.981 ? . 1_565 H(6) H(25) 2.822 ? . 1_554 H(7) O(1) 3.364 ? . 2_777 H(7) O(3) 2.924 ? . 1_465 H(7) H(9) 3.441 ? . 2_777 H(7) H(11) 3.492 ? . 2_777 H(7) H(23) 3.524 ? . 1_465 H(7) H(27) 3.156 ? . 2_677 H(8) C(4) 3.467 ? . 2_687 H(8) C(10) 3.460 ? . 2_687 H(8) C(21) 3.480 ? . 2_777 H(8) H(3) 2.625 ? . 2_687 H(8) H(8) 2.606 ? . 2_687 H(8) H(13) 3.442 ? . 2_777 H(8) H(16) 2.727 ? . 2_777 H(8) H(18) 3.263 ? . 2_777 H(8) H(19) 2.920 ? . 1_465 H(8) H(19) 3.586 ? . 2_777 H(9) O(4) 3.209 ? . 2_767 H(9) N(4) 3.313 ? . 2_777 H(9) C(8) 3.066 ? . 2_777 H(9) C(9) 3.330 ? . 2_777 H(9) C(13) 3.049 ? . 2_777 H(9) C(16) 3.462 ? . 2_777 H(9) C(24) 3.588 ? . 2_767 H(9) H(7) 3.441 ? . 2_777 H(9) H(21) 3.281 ? . 2_767 H(9) H(22) 2.983 ? . 2_767 H(9) H(32) 2.814 ? . 2_777 H(10) O(4) 3.413 ? . 2_767 H(10) C(2) 3.068 ? . 2_677 H(10) C(3) 3.285 ? . 2_677 H(10) C(24) 3.394 ? . 2_767 H(10) H(1) 2.988 ? . 2_677 H(10) H(2) 3.365 ? . 2_677 H(10) H(21) 2.693 ? . 2_767 H(10) H(22) 3.212 ? . 2_767 H(10) H(24) 3.156 ? . 2_766 H(10) H(28) 3.002 ? . 2_677 H(11) C(6) 3.262 ? . 2_776 H(11) C(7) 3.311 ? . 2_776 H(11) C(9) 3.040 ? . 2_777 H(11) C(10) 3.273 ? . 2_777 H(11) C(11) 2.953 ? . 2_777 H(11) C(12) 3.087 ? . 2_777 H(11) C(13) 3.271 ? . 2_777 H(11) C(14) 3.370 ? . 2_777 H(11) H(5) 2.650 ? . 2_776 H(11) H(6) 2.754 ? . 2_776 H(11) H(7) 3.492 ? . 2_777 H(11) H(25) 3.295 ? . 2_777 H(12) C(6) 3.165 ? . 2_776 H(12) C(7) 3.255 ? . 2_776 H(12) C(23) 3.256 ? . 2_766 H(12) C(24) 3.379 ? . 2_766 H(12) C(25) 3.354 ? . 2_766 H(12) H(5) 2.531 ? . 2_776 H(12) H(6) 2.717 ? . 2_776 H(12) H(20) 2.442 ? . 2_766 H(12) H(22) 3.093 ? . 2_766 H(12) H(24) 2.557 ? . 2_766 H(13) C(5) 3.026 ? . 2_777 H(13) C(6) 3.575 ? . 2_777 H(13) C(10) 3.260 ? . 2_777 H(13) C(13) 3.497 ? . 2_777 H(13) C(14) 2.945 ? . 2_777 H(13) C(22) 3.293 ? . 2_767 H(13) H(4) 3.232 ? . 2_777 H(13) H(8) 3.442 ? . 2_777 H(13) H(17) 2.693 ? . 2_767 H(13) H(18) 3.020 ? . 2_767 H(13) H(21) 3.424 ? . 2_767 H(13) H(22) 3.177 ? . 2_767 H(14) C(3) 3.449 ? . 2_677 H(14) C(22) 3.431 ? . 2_767 H(14) H(2) 3.079 ? . 2_677 H(14) H(17) 3.261 ? . 2_767 H(14) H(18) 2.737 ? . 2_767 H(14) H(20) 3.149 ? . 2_766 H(14) H(21) 3.198 ? . 2_767 H(15) C(6) 3.502 ? . 2_776 H(15) C(21) 3.257 ? . 2_766 H(15) C(22) 3.459 ? . 2_766 H(15) C(23) 3.452 ? . 2_766 H(15) H(5) 2.585 ? . 2_776 H(15) H(15) 2.408 ? . 2_766 H(15) H(17) 3.215 ? . 2_766 H(15) H(20) 2.663 ? . 2_766 H(16) C(4) 3.345 ? . 2_777 H(16) C(6) 3.584 ? . 2_776 H(16) C(10) 2.857 ? . 2_777 H(16) C(12) 3.119 ? . 2_777 H(16) C(14) 3.571 ? . 2_777 H(16) H(3) 3.237 ? . 2_777 H(16) H(5) 2.700 ? . 2_776 H(16) H(8) 2.727 ? . 2_777 H(17) C(5) 3.249 ? . 1_545 H(17) C(6) 3.170 ? . 1_545 H(17) C(20) 3.402 ? . 2_767 H(17) H(4) 3.106 ? . 1_545 H(17) H(5) 2.952 ? . 1_545 H(17) H(13) 2.693 ? . 2_767 H(17) H(14) 3.261 ? . 2_767 H(17) H(15) 3.215 ? . 2_766 H(17) H(17) 3.550 ? . 2_767 H(17) H(18) 3.090 ? . 2_767 H(18) C(4) 3.570 ? . 1_645 H(18) C(20) 3.314 ? . 2_767 H(18) H(3) 3.214 ? . 1_645 H(18) H(4) 3.272 ? . 2_777 H(18) H(8) 3.263 ? . 2_777 H(18) H(13) 3.020 ? . 2_767 H(18) H(14) 2.737 ? . 2_767 H(18) H(17) 3.090 ? . 2_767 H(18) H(18) 3.393 ? . 2_767 H(19) C(10) 3.022 ? . 1_645 H(19) C(12) 3.392 ? . 1_645 H(19) C(14) 3.570 ? . 1_645 H(19) H(2) 3.060 ? . 1_644 H(19) H(8) 2.920 ? . 1_645 H(19) H(8) 3.586 ? . 2_777 H(20) C(19) 3.272 ? . 2_766 H(20) C(20) 3.430 ? . 2_766 H(20) C(21) 3.441 ? . 2_766 H(20) H(2) 2.996 ? . 1_644 H(20) H(5) 3.326 ? . 1_545 H(20) H(12) 2.442 ? . 2_766 H(20) H(14) 3.149 ? . 2_766 H(20) H(15) 2.663 ? . 2_766 H(21) C(3) 3.374 ? . 1_645 H(21) C(4) 3.117 ? . 1_645 H(21) C(11) 3.367 ? . 1_645 H(21) C(12) 3.094 ? . 1_645 H(21) C(18) 3.416 ? . 2_767 H(21) H(3) 3.490 ? . 1_645 H(21) H(9) 3.281 ? . 2_767 H(21) H(10) 2.693 ? . 2_767 H(21) H(13) 3.424 ? . 2_767 H(21) H(14) 3.198 ? . 2_767 H(22) C(6) 3.068 ? . 1_545 H(22) C(7) 2.972 ? . 1_545 H(22) C(18) 3.544 ? . 2_767 H(22) H(5) 3.138 ? . 1_545 H(22) H(6) 2.981 ? . 1_545 H(22) H(9) 2.983 ? . 2_767 H(22) H(10) 3.212 ? . 2_767 H(22) H(12) 3.093 ? . 2_766 H(22) H(13) 3.177 ? . 2_767 H(22) H(32) 3.242 ? . 1_545 H(23) C(2) 3.357 ? . 1_644 H(23) C(9) 3.045 ? . 1_645 H(23) C(10) 3.230 ? . 1_645 H(23) C(11) 3.196 ? . 1_645 H(23) C(12) 3.272 ? . 1_645 H(23) C(13) 2.999 ? . 1_645 H(23) C(14) 3.116 ? . 1_645 H(23) H(1) 2.612 ? . 1_644 H(23) H(2) 3.202 ? . 1_644 H(23) H(7) 3.524 ? . 1_645 H(23) H(29) 3.250 ? . 1_645 H(24) O(2) 2.795 ? . 2_766 H(24) C(2) 3.294 ? . 1_644 H(24) C(17) 3.000 ? . 2_766 H(24) C(18) 3.311 ? . 2_766 H(24) C(19) 3.322 ? . 2_766 H(24) H(1) 2.524 ? . 1_644 H(24) H(2) 3.209 ? . 1_644 H(24) H(10) 3.156 ? . 2_766 H(24) H(12) 2.557 ? . 2_766 H(25) O(1) 1.88(3) ? . 2_777 H(25) O(4) 3.49(3) ? . 2_767 H(25) N(4) 3.32(3) ? . 2_777 H(25) C(7) 3.50(3) ? . 1_556 H(25) C(17) 3.04(3) ? . 2_777 H(25) H(6) 2.822 ? . 1_556 H(25) H(11) 3.295 ? . 2_777 H(25) H(31) 2.60(4) ? . 2_777 H(25) H(32) 3.32(4) ? . 2_777 H(26) O(1) 3.23(3) ? . 2_777 H(26) O(3) 2.77(4) ? . 2_767 H(26) O(4) 1.87(3) ? . 2_767 H(26) N(1) 3.51(3) ? . 2_677 H(26) N(3) 3.44(3) ? . 1_556 H(26) N(4) 3.03(3) ? . 2_777 H(26) C(26) 2.62(4) ? . 2_767 H(26) H(28) 3.37(5) ? . . H(26) H(28) 3.37(4) ? . 2_677 H(26) H(30) 3.53(5) ? . 1_556 H(26) H(31) 2.80(4) ? . 2_777 H(26) H(32) 2.52(4) ? . 2_777 H(27) O(2) 3.17(3) ? . 2_677 H(27) O(3) 1.77(3) ? . 2_767 H(27) O(4) 2.89(3) ? . 2_767 H(27) N(1) 3.35(3) ? . 2_677 H(27) N(3) 3.44(3) ? . 1_556 H(27) N(3) 3.03(4) ? . 2_677 H(27) C(15) 3.45(3) ? . 2_677 H(27) C(26) 2.63(3) ? . 2_767 H(27) H(7) 3.156 ? . 2_677 H(27) H(27) 3.47(5) ? . 2_677 H(27) H(28) 1.69(5) ? . . H(27) H(29) 3.36(4) ? . 1_556 H(27) H(29) 2.56(5) ? . 2_677 H(27) H(30) 3.53(4) ? . 1_556 H(27) H(30) 2.82(5) ? . 2_677 H(28) O(2) 1.91(4) ? . 2_677 H(28) O(3) 3.32(3) ? . 2_767 H(28) O(4) 3.55(3) ? . 1_465 H(28) N(1) 0.93(4) ? . . H(28) N(2) 3.11(4) ? . . H(28) N(3) 3.26(4) ? . 2_677 H(28) C(1) 2.51(4) ? . . H(28) C(2) 2.62(4) ? . . H(28) C(15) 1.93(4) ? . . H(28) C(17) 3.00(4) ? . 2_677 H(28) C(18) 3.49(3) ? . 2_677 H(28) H(1) 2.272 ? . . H(28) H(10) 3.002 ? . 2_677 H(28) H(26) 3.37(5) ? . . H(28) H(26) 3.37(4) ? . 2_677 H(28) H(27) 1.69(5) ? . . H(28) H(29) 3.26(5) ? . 2_677 H(28) H(30) 2.57(6) ? . 2_677 H(29) O(2) 3.25(3) ? . . H(29) O(3) 1.97(3) ? . 1_465 H(29) O(3) 3.56(3) ? . 2_766 H(29) N(1) 3.41(3) ? . 1_554 H(29) N(1) 3.22(3) ? . 2_677 H(29) C(15) 3.56(3) ? . 1_554 H(29) C(26) 3.14(3) ? . 1_465 H(29) H(1) 3.204 ? . 1_554 H(29) H(23) 3.250 ? . 1_465 H(29) H(27) 3.36(4) ? . 1_554 H(29) H(27) 2.56(5) ? . 2_677 H(29) H(28) 3.26(5) ? . 2_677 H(30) O(1) 3.02(3) ? . . H(30) O(2) 1.79(3) ? . . H(30) O(3) 3.16(3) ? . 1_465 H(30) O(3) 3.02(3) ? . 2_766 H(30) O(4) 3.52(3) ? . 2_766 H(30) N(1) 2.99(4) ? . 2_677 H(30) C(17) 2.72(3) ? . . H(30) C(26) 3.27(3) ? . 2_766 H(30) H(26) 3.53(5) ? . 1_554 H(30) H(27) 3.53(4) ? . 1_554 H(30) H(27) 2.82(5) ? . 2_677 H(30) H(28) 2.57(6) ? . 2_677 H(31) O(1) 1.94(3) ? . . H(31) O(2) 2.80(4) ? . . H(31) O(4) 3.22(4) ? . 1_565 H(31) N(2) 3.01(3) ? . 2_777 H(31) N(4) 3.21(3) ? . 2_776 H(31) C(17) 2.67(4) ? . . H(31) H(25) 2.60(4) ? . 2_777 H(31) H(26) 2.80(4) ? . 2_777 H(31) H(31) 3.17(5) ? . 2_776 H(31) H(32) 3.34(4) ? . 2_776 H(32) O(1) 3.46(3) ? . . H(32) O(4) 1.88(3) ? . 1_565 H(32) N(2) 3.23(3) ? . 2_777 H(32) C(26) 3.00(3) ? . 1_565 H(32) H(9) 2.814 ? . 2_777 H(32) H(22) 3.242 ? . 1_565 H(32) H(25) 3.32(4) ? . 2_777 H(32) H(26) 2.52(4) ? . 2_777 H(32) H(31) 3.34(4) ? . 2_776 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================