Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author 'Prof Andrew Hamilton ' _publ_contact_author_address ; Department of Chemistry Yale University 225 Prospect St. PO Box 6666 New Haven CT 06511 UNITED STATES OF AMERICA ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ANDREW.HAMILTON@YALE.EDU _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_experimental ; ; _publ_section_comment ; ; _publ_section_references ; Molecular Structure Corporation (1985, 1992). teXsan. Crystal Structure Analysis Package, The Woodlands, TX, USA 77381 ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ; _publ_section_figure_captions ; ; _publ_contact_author_name 'Prof Andrew Hamilton' loop_ _publ_author_name A.Hamilton M.Blaskovich 'Cynthia Bucher ' 'Dora Carrico ' 'Hairuo Peng ' ; E.E.Pusateri ; 'Said M. Sebti ' 'Van Thai ' # Attachment 'B517572_compd_3.cif' data_SRH462_HAMILTON_-_PENG _database_code_depnum_ccdc_archive 'CCDC 292695' #------------------------------------------------------------------------------ _audit_creation_date 'Mon Oct 3 13:03:03 2000' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution ? _computing_structure_refinement teXsan _computing_publication_material teXsan #------------------------------------------------------------------------------ _cell_length_a 12.174(1) _cell_length_b 21.549(1) _cell_length_c 7.6755(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2013.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 183.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas ? _chemical_formula_weight 396.46 _chemical_formula_analytical ? _chemical_formula_sum 'C23 H25 F N2 O3 ' _chemical_formula_moiety 'C23 H25 F N2 O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 840.00 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 183.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector ? _diffrn_measurement_device unknown _diffrn_measurement_method 'omega scans with profile analysis' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 _diffrn_standard_refln_index_h ? _diffrn_standard_refln_index_k ? _diffrn_standard_refln_index_l ? _diffrn_reflns_number 4459 _reflns_number_total 2639 _reflns_number_observed 1645 _reflns_observed_criterion 3.00 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max 27.48 _diffrn_reflns_reduction_process ? _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 92 0.003 0.002 'International Tables' H 0 100 0.000 0.000 'International Tables' N 0 8 0.006 0.003 'International Tables' O 0 12 0.011 0.006 'International Tables' F 0 4 0.017 0.010 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom F(1) 0.6883(2) 0.43533(10) 1.2060(2) 0.0560(6) Uij ? ? O(1) 0.2904(2) 0.3702(1) 0.5359(3) 0.0413(7) Uij ? ? O(2) 0.3227(2) 0.15429(9) 0.4989(3) 0.0381(6) Uij ? ? O(3) 0.5075(2) 0.14654(9) 0.5265(3) 0.0359(6) Uij ? ? N(1) 0.4364(2) 0.2342(1) 0.4271(3) 0.0244(7) Uij ? ? N(2) 0.4731(2) 0.3588(1) 0.4797(3) 0.0276(7) Uij ? ? C(1) 0.3661(2) 0.3394(1) 0.4781(4) 0.0288(9) Uij ? ? C(2) 0.3472(2) 0.2781(1) 0.3855(4) 0.0273(8) Uij ? ? C(3) 0.5433(2) 0.2583(1) 0.4125(4) 0.0272(8) Uij ? ? C(4) 0.5590(2) 0.3184(2) 0.4323(4) 0.0288(8) Uij ? ? C(5) 0.3395(2) 0.2898(1) 0.1879(3) 0.0287(8) Uij ? ? C(6) 0.2873(2) 0.2384(1) 0.0803(4) 0.0310(9) Uij ? ? C(7) 0.1635(3) 0.2359(2) 0.1082(4) 0.047(1) Uij ? ? C(8) 0.3129(3) 0.2480(2) -0.1112(4) 0.047(1) Uij ? ? C(9) 0.4138(2) 0.1765(1) 0.4866(3) 0.0276(8) Uij ? ? C(10) 0.4998(3) 0.0834(2) 0.5927(4) 0.042(1) Uij ? ? C(11) 0.5490(3) 0.0808(1) 0.7708(4) 0.0316(9) Uij ? ? C(12) 0.4902(3) 0.0999(2) 0.9147(5) 0.048(1) Uij ? ? C(13) 0.5368(4) 0.0987(2) 1.0776(5) 0.066(1) Uij ? ? C(14) 0.6417(5) 0.0771(2) 1.0990(5) 0.067(1) Uij ? ? C(15) 0.7008(3) 0.0574(2) 0.9583(5) 0.053(1) Uij ? ? C(16) 0.6550(3) 0.0593(2) 0.7945(4) 0.0399(10) Uij ? ? C(17) 0.4999(2) 0.4221(2) 0.5391(4) 0.0347(9) Uij ? ? C(18) 0.5511(3) 0.4242(1) 0.7187(4) 0.0283(8) Uij ? ? C(19) 0.6613(2) 0.4380(1) 0.7385(4) 0.0338(9) Uij ? ? C(20) 0.7075(2) 0.4423(2) 0.9022(4) 0.0372(10) Uij ? ? C(21) 0.6425(3) 0.4321(2) 1.0430(4) 0.0360(9) Uij ? ? C(22) 0.5328(2) 0.4174(2) 1.0307(4) 0.0339(9) Uij ? ? C(23) 0.4889(2) 0.4136(2) 0.8651(4) 0.0336(9) Uij ? ? H(1) 0.2796 0.2610 0.4244 0.0328 Uij ? ? H(2) 0.6035 0.2316 0.3886 0.0327 Uij ? ? H(3) 0.6304 0.3350 0.4140 0.0346 Uij ? ? H(4) 0.2975 0.3265 0.1707 0.0344 Uij ? ? H(5) 0.4119 0.2961 0.1453 0.0344 Uij ? ? H(6) 0.3180 0.1999 0.1159 0.0372 Uij ? ? H(7) 0.1330 0.2759 0.0899 0.0570 Uij ? ? H(8) 0.1320 0.2074 0.0281 0.0570 Uij ? ? H(9) 0.1484 0.2227 0.2238 0.0570 Uij ? ? H(10) 0.3901 0.2519 -0.1262 0.0559 Uij ? ? H(11) 0.2871 0.2134 -0.1761 0.0559 Uij ? ? H(12) 0.2777 0.2847 -0.1512 0.0559 Uij ? ? H(13) 0.4248 0.0713 0.5981 0.0504 Uij ? ? H(14) 0.5385 0.0561 0.5173 0.0504 Uij ? ? H(15) 0.4168 0.1140 0.9010 0.0573 Uij ? ? H(16) 0.4962 0.1129 1.1755 0.0787 Uij ? ? H(17) 0.6734 0.0758 1.2121 0.0798 Uij ? ? H(18) 0.7736 0.0423 0.9734 0.0641 Uij ? ? H(19) 0.6965 0.0457 0.6969 0.0478 Uij ? ? H(20) 0.5500 0.4399 0.4586 0.0416 Uij ? ? H(21) 0.4341 0.4458 0.5411 0.0416 Uij ? ? H(22) 0.7057 0.4445 0.6383 0.0406 Uij ? ? H(23) 0.7831 0.4521 0.9160 0.0446 Uij ? ? H(24) 0.4893 0.4102 1.1314 0.0407 Uij ? ? H(25) 0.4135 0.4033 0.8520 0.0404 Uij ? ? 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) 0.067(1) 0.067(2) 0.033(1) -0.021(1) -0.015(1) 0.003(1) O(1) 0.037(1) 0.045(1) 0.043(1) 0.013(1) 0.002(1) -0.010(1) O(2) 0.034(1) 0.036(1) 0.044(1) -0.009(1) 0.001(1) 0.001(1) O(3) 0.037(1) 0.028(1) 0.043(1) 0.0011(10) -0.009(1) 0.008(1) N(1) 0.021(1) 0.025(1) 0.027(1) 0.002(1) 0.000(1) 0.005(1) N(2) 0.030(1) 0.027(1) 0.026(1) 0.002(1) 0.000(1) -0.002(1) C(1) 0.031(2) 0.032(2) 0.023(2) 0.006(1) -0.002(2) 0.004(2) C(2) 0.023(2) 0.032(2) 0.027(1) 0.001(1) 0.000(1) 0.003(2) C(3) 0.022(2) 0.032(2) 0.028(2) -0.002(1) 0.001(1) 0.004(2) C(4) 0.027(2) 0.033(2) 0.027(2) -0.003(1) 0.002(1) 0.002(2) C(5) 0.030(2) 0.030(2) 0.026(1) 0.000(1) -0.003(1) 0.002(2) C(6) 0.035(2) 0.029(2) 0.029(2) 0.004(1) -0.005(2) 0.000(2) C(7) 0.045(2) 0.059(2) 0.039(2) -0.015(2) -0.007(2) -0.008(2) C(8) 0.046(2) 0.061(3) 0.032(2) 0.002(2) -0.006(2) -0.010(2) C(9) 0.033(2) 0.030(2) 0.020(1) 0.001(2) -0.003(2) -0.003(2) C(10) 0.055(2) 0.026(2) 0.045(2) -0.003(2) -0.011(2) 0.003(2) C(11) 0.040(2) 0.022(2) 0.033(2) -0.004(2) -0.004(2) 0.003(2) C(12) 0.052(2) 0.044(2) 0.048(2) 0.007(2) 0.008(2) 0.003(2) C(13) 0.109(4) 0.048(3) 0.039(2) -0.003(3) 0.013(3) -0.005(2) C(14) 0.103(3) 0.056(3) 0.041(2) -0.031(3) -0.032(3) 0.012(2) C(15) 0.044(2) 0.049(2) 0.067(3) -0.014(2) -0.022(2) 0.024(2) C(16) 0.035(2) 0.034(2) 0.051(2) -0.005(2) -0.001(2) 0.009(2) C(17) 0.044(2) 0.027(2) 0.033(2) 0.001(2) -0.003(2) -0.003(2) C(18) 0.039(2) 0.021(2) 0.025(1) 0.001(1) 0.002(2) -0.004(1) C(19) 0.036(2) 0.032(2) 0.034(2) -0.005(2) 0.004(2) 0.000(2) C(20) 0.035(2) 0.037(2) 0.039(2) -0.007(2) -0.004(2) 0.004(2) C(21) 0.046(2) 0.032(2) 0.029(2) -0.007(2) -0.012(2) -0.001(2) C(22) 0.042(2) 0.034(2) 0.025(2) -0.003(2) 0.003(2) -0.002(2) C(23) 0.032(2) 0.034(2) 0.034(2) -0.001(2) -0.001(2) -0.005(2) #------------------------------------------------------------------------------ _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1645 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0407 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0404 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.478 _refine_ls_shift/esd_max 0.0001 _refine_ls_shift/esd_mean ? _refine_diff_density_min -0.18 _refine_diff_density_max 0.20 #------------------------------------------------------------------------------ _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(21) 1.371(3) ? ? yes O(1) C(1) 1.219(3) ? ? yes O(2) C(9) 1.211(3) ? ? yes O(3) C(9) 1.346(3) ? ? yes O(3) C(10) 1.454(4) ? ? yes N(1) C(2) 1.475(4) ? ? yes N(1) C(3) 1.406(3) ? ? yes N(1) C(9) 1.354(4) ? ? yes N(2) C(1) 1.368(4) ? ? yes N(2) C(4) 1.409(4) ? ? yes N(2) C(17) 1.473(4) ? ? yes C(1) C(2) 1.518(4) ? ? yes C(2) C(5) 1.540(4) ? ? yes C(3) C(4) 1.318(4) ? ? yes C(5) C(6) 1.520(4) ? ? yes C(6) C(7) 1.523(4) ? ? yes C(6) C(8) 1.517(4) ? ? yes C(10) C(11) 1.494(4) ? ? yes C(11) C(12) 1.378(4) ? ? yes C(11) C(16) 1.383(4) ? ? yes C(12) C(13) 1.373(6) ? ? yes C(13) C(14) 1.369(6) ? ? yes C(14) C(15) 1.366(6) ? ? yes C(15) C(16) 1.376(4) ? ? yes C(17) C(18) 1.513(4) ? ? yes C(18) C(19) 1.383(4) ? ? yes C(18) C(23) 1.374(4) ? ? yes C(19) C(20) 1.380(4) ? ? yes C(20) C(21) 1.357(4) ? ? yes C(21) C(22) 1.376(4) ? ? yes C(22) C(23) 1.381(4) ? ? yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(9) O(3) C(10) 118.2(2) ? ? ? yes C(2) N(1) C(3) 115.3(2) ? ? ? yes C(2) N(1) C(9) 120.9(2) ? ? ? yes C(3) N(1) C(9) 123.7(2) ? ? ? yes C(1) N(2) C(4) 121.0(2) ? ? ? yes C(1) N(2) C(17) 119.8(2) ? ? ? yes C(4) N(2) C(17) 119.1(2) ? ? ? yes O(1) C(1) N(2) 123.3(3) ? ? ? yes O(1) C(1) C(2) 122.0(3) ? ? ? yes N(2) C(1) C(2) 114.5(2) ? ? ? yes N(1) C(2) C(1) 110.2(2) ? ? ? yes N(1) C(2) C(5) 111.3(2) ? ? ? yes C(1) C(2) C(5) 109.1(3) ? ? ? yes N(1) C(3) C(4) 119.2(3) ? ? ? yes N(2) C(4) C(3) 122.0(3) ? ? ? yes C(2) C(5) C(6) 116.1(3) ? ? ? yes C(5) C(6) C(7) 111.3(3) ? ? ? yes C(5) C(6) C(8) 109.9(3) ? ? ? yes C(7) C(6) C(8) 110.1(3) ? ? ? yes O(2) C(9) O(3) 124.7(3) ? ? ? yes O(2) C(9) N(1) 125.1(3) ? ? ? yes O(3) C(9) N(1) 110.2(2) ? ? ? yes O(3) C(10) C(11) 109.2(3) ? ? ? yes C(10) C(11) C(12) 120.9(3) ? ? ? yes C(10) C(11) C(16) 120.5(3) ? ? ? yes C(12) C(11) C(16) 118.6(3) ? ? ? yes C(11) C(12) C(13) 120.6(3) ? ? ? yes C(12) C(13) C(14) 120.1(4) ? ? ? yes C(13) C(14) C(15) 120.1(3) ? ? ? yes C(14) C(15) C(16) 120.0(3) ? ? ? yes C(11) C(16) C(15) 120.6(3) ? ? ? yes N(2) C(17) C(18) 113.7(3) ? ? ? yes C(17) C(18) C(19) 120.4(3) ? ? ? yes C(17) C(18) C(23) 120.9(2) ? ? ? yes C(19) C(18) C(23) 118.7(3) ? ? ? yes C(18) C(19) C(20) 120.7(3) ? ? ? yes C(19) C(20) C(21) 118.5(3) ? ? ? yes F(1) C(21) C(20) 118.8(3) ? ? ? yes F(1) C(21) C(22) 118.0(3) ? ? ? yes C(20) C(21) C(22) 123.2(3) ? ? ? yes C(21) C(22) C(23) 116.9(3) ? ? ? yes C(18) C(23) C(22) 122.0(3) ? ? ? yes #------------------------------------------------------------------------------ # Attachment 'B517572_compd_12a.cif' data_SRH463_HAMILTON_-_PENG _database_code_depnum_ccdc_archive 'CCDC 292696' #------------------------------------------------------------------------------ _audit_creation_date 'Mon Oct 10 15:14:07 2000' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution ? _computing_structure_refinement teXsan _computing_publication_material teXsan #------------------------------------------------------------------------------ _cell_length_a 7.884(1) _cell_length_b 5.6159(4) _cell_length_c 17.964(1) _cell_angle_alpha 90 _cell_angle_beta 90.753(4) _cell_angle_gamma 90 _cell_volume 795.3(1) _cell_formula_units_Z 2 _cell_measurement_temperature 183.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_meas ? _chemical_formula_weight 322.36 _chemical_formula_analytical ? _chemical_formula_sum 'C19 H18 N2 O3 ' _chemical_formula_moiety 'C19 H18 N2 O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 340.00 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 183.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector ? _diffrn_measurement_device unknown _diffrn_measurement_method 'omega scans with profile analysis' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 _diffrn_standard_refln_index_h ? _diffrn_standard_refln_index_k ? _diffrn_standard_refln_index_l ? _diffrn_reflns_number 2796 _reflns_number_total 1563 _reflns_number_observed 1148 _reflns_observed_criterion 3.00 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max 24.99 _diffrn_reflns_reduction_process ? _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 38 0.003 0.002 'International Tables' H 0 36 0.000 0.000 'International Tables' N 0 4 0.006 0.003 'International Tables' O 0 6 0.011 0.006 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.9225(3) 0.0038 0.4274(1) 0.0433(8) Uij ? ? O(2) 0.2570(3) 0.3374(8) 0.3704(1) 0.0404(8) Uij ? ? O(3) 0.3960(2) 0.0261(8) 0.3174(1) 0.0345(7) Uij ? ? N(1) 0.5452(3) 0.3096(8) 0.3771(1) 0.0288(8) Uij ? ? N(2) 0.8172(3) 0.3547(9) 0.4716(1) 0.041(1) Uij ? ? C(1) 0.8229(4) 0.173(1) 0.4229(2) 0.034(1) Uij ? ? C(2) 0.7046(4) 0.196(1) 0.3555(1) 0.0290(9) Uij ? ? C(3) 0.5595(4) 0.513(1) 0.4223(2) 0.037(1) Uij ? ? C(4) 0.6951(4) 0.534(1) 0.4667(2) 0.041(1) Uij ? ? C(5) 0.8004(4) 0.3475(10) 0.2978(1) 0.034(1) Uij ? ? C(6) 0.7158(4) 0.3657(10) 0.2225(2) 0.0280(10) Uij ? ? C(7) 0.7453(4) 0.1946(10) 0.1690(2) 0.034(1) Uij ? ? C(8) 0.6763(4) 0.212(1) 0.0978(2) 0.039(1) Uij ? ? C(9) 0.5754(4) 0.407(1) 0.0800(2) 0.039(1) Uij ? ? C(10) 0.5414(4) 0.578(1) 0.1330(2) 0.040(1) Uij ? ? C(11) 0.6126(4) 0.558(1) 0.2041(2) 0.035(1) Uij ? ? C(12) 0.3874(4) 0.232(1) 0.3557(2) 0.028(1) Uij ? ? C(13) 0.2361(4) -0.0940(10) 0.3025(2) 0.0347(10) Uij ? ? C(14) 0.1922(4) -0.0971(10) 0.2207(2) 0.0271(10) Uij ? ? C(15) 0.2359(4) 0.083(1) 0.1730(2) 0.038(1) Uij ? ? C(16) 0.1869(4) 0.074(1) 0.0982(2) 0.038(1) Uij ? ? C(17) 0.0916(4) -0.116(1) 0.0719(2) 0.039(1) Uij ? ? C(18) 0.0464(4) -0.297(1) 0.1194(2) 0.039(1) Uij ? ? C(19) 0.0978(4) -0.288(1) 0.1936(2) 0.033(1) Uij ? ? H(1) 0.6819 0.0423 0.3355 0.0348 Uij ? ? H(2) 0.4745 0.6333 0.4212 0.0444 Uij ? ? H(3) 0.7091 0.6742 0.4957 0.0497 Uij ? ? H(4) 0.907(4) 0.364(9) 0.506(2) 0.06(1) Uij ? ? H(5) 0.8124 0.5039 0.3173 0.0413 Uij ? ? H(6) 0.9095 0.2791 0.2913 0.0413 Uij ? ? H(7) 0.8146 0.0615 0.1812 0.0405 Uij ? ? H(8) 0.6980 0.0930 0.0617 0.0474 Uij ? ? H(9) 0.5293 0.4222 0.0311 0.0474 Uij ? ? H(10) 0.4698 0.7089 0.1210 0.0475 Uij ? ? H(11) 0.5903 0.6766 0.2403 0.0426 Uij ? ? H(12) 0.2441 -0.2535 0.3199 0.0416 Uij ? ? H(13) 0.1487 -0.0137 0.3283 0.0416 Uij ? ? H(14) 0.2999 0.2148 0.1911 0.0458 Uij ? ? H(15) 0.2191 0.1978 0.0653 0.0460 Uij ? ? H(16) 0.0572 -0.1211 0.0210 0.0466 Uij ? ? H(17) -0.0196 -0.4266 0.1015 0.0468 Uij ? ? H(18) 0.0682 -0.4142 0.2262 0.0400 Uij ? ? 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) 0.032(1) 0.055(2) 0.043(1) 0.001(2) -0.008(1) 0.015(2) O(2) 0.033(1) 0.037(2) 0.051(1) 0.006(2) 0.002(1) 0.002(2) O(3) 0.025(1) 0.038(2) 0.041(1) -0.003(1) -0.0058(9) -0.011(2) N(1) 0.026(1) 0.031(2) 0.030(1) 0.001(2) -0.002(1) -0.001(2) N(2) 0.036(2) 0.055(3) 0.031(1) -0.006(2) -0.010(1) -0.002(2) C(1) 0.027(2) 0.045(3) 0.030(2) -0.008(2) -0.003(1) 0.011(2) C(2) 0.027(2) 0.032(3) 0.028(2) 0.000(2) -0.004(1) 0.002(2) C(3) 0.042(2) 0.034(3) 0.035(2) -0.003(2) 0.002(2) -0.003(2) C(4) 0.052(2) 0.040(3) 0.032(2) -0.006(3) 0.000(2) -0.003(2) C(5) 0.035(2) 0.038(3) 0.030(2) -0.001(2) -0.002(1) 0.000(2) C(6) 0.029(2) 0.028(3) 0.027(2) -0.001(2) 0.001(1) 0.003(2) C(7) 0.032(2) 0.034(3) 0.035(2) 0.005(2) -0.001(1) 0.007(2) C(8) 0.041(2) 0.042(3) 0.036(2) -0.006(2) 0.003(2) -0.007(3) C(9) 0.035(2) 0.050(3) 0.034(2) -0.004(2) -0.007(2) 0.011(3) C(10) 0.032(2) 0.039(3) 0.048(2) 0.004(2) -0.001(2) 0.010(3) C(11) 0.038(2) 0.033(3) 0.036(2) -0.003(2) 0.002(2) 0.002(2) C(12) 0.033(2) 0.027(3) 0.024(2) 0.001(2) -0.002(1) 0.004(2) C(13) 0.027(2) 0.035(3) 0.042(2) -0.004(2) -0.006(1) 0.002(2) C(14) 0.020(2) 0.026(3) 0.036(2) -0.001(2) -0.003(1) 0.003(2) C(15) 0.035(2) 0.035(3) 0.044(2) -0.004(2) -0.005(2) 0.002(3) C(16) 0.041(2) 0.033(3) 0.041(2) 0.003(2) 0.000(2) 0.012(2) C(17) 0.035(2) 0.048(3) 0.033(2) 0.003(2) -0.002(1) -0.001(2) C(18) 0.037(2) 0.038(3) 0.042(2) -0.003(2) -0.002(2) -0.009(3) C(19) 0.032(2) 0.028(3) 0.040(2) -0.004(2) 0.003(1) 0.000(2) #------------------------------------------------------------------------------ _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1148 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0404 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0418 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.508 _refine_ls_shift/esd_max 0.0001 _refine_ls_shift/esd_mean ? _refine_diff_density_min -0.18 _refine_diff_density_max 0.17 #------------------------------------------------------------------------------ _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(1) 1.236(5) ? ? yes O(2) C(12) 1.218(4) ? ? yes O(3) C(12) 1.349(4) ? ? yes O(3) C(13) 1.452(4) ? ? yes N(1) C(2) 1.467(4) ? ? yes N(1) C(3) 1.407(5) ? ? yes N(1) C(12) 1.367(4) ? ? yes N(2) C(1) 1.344(6) ? ? yes N(2) C(4) 1.395(6) ? ? yes C(1) C(2) 1.523(4) ? ? yes C(2) C(5) 1.547(5) ? ? yes C(3) C(4) 1.330(4) ? ? yes C(5) C(6) 1.503(4) ? ? yes C(6) C(7) 1.382(5) ? ? yes C(6) C(11) 1.389(5) ? ? yes C(7) C(8) 1.386(4) ? ? yes C(8) C(9) 1.385(6) ? ? yes C(9) C(10) 1.382(6) ? ? yes C(10) C(11) 1.393(4) ? ? yes C(13) C(14) 1.506(4) ? ? yes C(14) C(15) 1.372(5) ? ? yes C(14) C(19) 1.390(5) ? ? yes C(15) C(16) 1.394(4) ? ? yes C(16) C(17) 1.383(6) ? ? yes C(17) C(18) 1.377(6) ? ? yes C(18) C(19) 1.388(4) ? ? yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(12) O(3) C(13) 116.3(3) ? ? ? yes C(2) N(1) C(3) 116.4(3) ? ? ? yes C(2) N(1) C(12) 124.5(3) ? ? ? yes C(3) N(1) C(12) 119.1(3) ? ? ? yes C(1) N(2) C(4) 122.3(3) ? ? ? yes O(1) C(1) N(2) 124.6(3) ? ? ? yes O(1) C(1) C(2) 119.8(4) ? ? ? yes N(2) C(1) C(2) 115.4(4) ? ? ? yes N(1) C(2) C(1) 110.1(3) ? ? ? yes N(1) C(2) C(5) 111.4(3) ? ? ? yes C(1) C(2) C(5) 106.2(2) ? ? ? yes N(1) C(3) C(4) 118.3(4) ? ? ? yes N(2) C(4) C(3) 121.6(4) ? ? ? yes C(2) C(5) C(6) 115.2(3) ? ? ? yes C(5) C(6) C(7) 120.1(3) ? ? ? yes C(5) C(6) C(11) 121.3(4) ? ? ? yes C(7) C(6) C(11) 118.5(3) ? ? ? yes C(6) C(7) C(8) 121.6(4) ? ? ? yes C(7) C(8) C(9) 119.2(4) ? ? ? yes C(8) C(9) C(10) 120.3(3) ? ? ? yes C(9) C(10) C(11) 119.7(4) ? ? ? yes C(6) C(11) C(10) 120.7(4) ? ? ? yes O(2) C(12) O(3) 125.1(3) ? ? ? yes O(2) C(12) N(1) 123.6(4) ? ? ? yes O(3) C(12) N(1) 111.3(3) ? ? ? yes O(3) C(13) C(14) 111.9(3) ? ? ? yes C(13) C(14) C(15) 123.0(3) ? ? ? yes C(13) C(14) C(19) 117.8(3) ? ? ? yes C(15) C(14) C(19) 119.2(3) ? ? ? yes C(14) C(15) C(16) 120.3(3) ? ? ? yes C(15) C(16) C(17) 120.0(4) ? ? ? yes C(16) C(17) C(18) 120.0(3) ? ? ? yes C(17) C(18) C(19) 119.7(4) ? ? ? yes C(14) C(19) C(18) 120.7(4) ? ? ? yes #------------------------------------------------------------------------------