data_C20H14ClF3N4O3(15) _publ_contact_author_name 'Koya Prabhakara Rao' _publ_contact_author_address ; New Generation Materials Lab (NGML), Department of Science and Humanities Vignan's Foundation for Science Technology and Research (VFSTR) University Vadlamudi, Guntur-522 213 Andhra Pradesh India ; _publ_contact_author_email kprao2005@gmail.com _publ_section_title ; Design and Synthesis of ‘Chloropicolinate Amides and Urea Derivatives’ as Novel Inhibitors for Mycobacterium Tuberculosis ; _publ_author_name ; 'Koya Prabhakara Rao' ; _publ_author_address ; New Generation Materials Lab (NGML), Department of Science and Humanities Vignan's Foundation for Science Technology and Research (VFSTR) (Deemed to be University), Vadlamudi, Guntur-522 213 Andhra Pradesh India ; #================================================================================== _publ_requested_journal 'ACS Omega' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20H14ClF3N4O3' _chemical_formula_weight 450.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 19.050(3) _cell_length_b 10.8747(14) _cell_length_c 19.747(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4090.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5809 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 22.23 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9574 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 68316 _diffrn_reflns_av_R_equivalents 0.0876 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5078 _reflns_number_gt 2942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3for Windows(Farrugia, 2012)' _computing_publication_material wingx _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+1.7421P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5078 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.49901(14) -0.1059(3) 0.39916(13) 0.0564(7) Uani 1 1 d . . . C2 C 0.53528(13) -0.1727(2) 0.34266(12) 0.0457(6) Uani 1 1 d . . . C3 C 0.51767(15) -0.2943(2) 0.32991(15) 0.0622(8) Uani 1 1 d . . . H3 H 0.4864 -0.3352 0.3582 0.075 Uiso 1 1 calc R . . C4 C 0.54643(17) -0.3538(3) 0.27570(17) 0.0710(9) Uani 1 1 d . . . H4 H 0.5370 -0.4365 0.2680 0.085 Uiso 1 1 calc R . . C5 C 0.58955(17) -0.2893(3) 0.23286(16) 0.0693(8) Uani 1 1 d . . . H5 H 0.6065 -0.3285 0.1943 0.083 Uiso 1 1 calc R . . C6 C 0.58365(13) -0.1172(2) 0.29928(12) 0.0444(6) Uani 1 1 d . . . C7 C 0.61463(12) 0.0086(2) 0.31233(12) 0.0434(6) Uani 1 1 d . . . C8 C 0.65939(12) 0.18912(19) 0.24926(11) 0.0385(5) Uani 1 1 d . . . C9 C 0.66346(15) 0.2694(2) 0.30395(13) 0.0566(7) Uani 1 1 d . . . H9 H 0.6499 0.2427 0.3467 0.068 Uiso 1 1 calc R . . C10 C 0.68729(15) 0.3876(2) 0.29544(14) 0.0643(8) Uani 1 1 d . . . H10 H 0.6896 0.4404 0.3324 0.077 Uiso 1 1 calc R . . C11 C 0.70767(14) 0.4282(2) 0.23295(14) 0.0563(7) Uani 1 1 d . . . H11 H 0.7218 0.5093 0.2270 0.068 Uiso 1 1 calc R . . C12 C 0.70710(12) 0.3484(2) 0.17917(12) 0.0464(6) Uani 1 1 d . . . H12 H 0.7225 0.3760 0.1371 0.056 Uiso 1 1 calc R . . C13 C 0.68421(11) 0.22756(19) 0.18564(11) 0.0355(5) Uani 1 1 d . . . C14 C 0.68977(11) 0.14373(18) 0.12640(10) 0.0342(5) Uani 1 1 d . . . C15 C 0.74701(12) 0.1500(2) 0.08401(11) 0.0404(5) Uani 1 1 d . . . H15 H 0.7817 0.2083 0.0922 0.048 Uiso 1 1 calc R . . C16 C 0.75408(12) 0.0706(2) 0.02899(11) 0.0395(5) Uani 1 1 d . . . C17 C 0.69938(12) -0.01494(19) 0.01976(10) 0.0361(5) Uani 1 1 d . . . C18 C 0.64414(11) -0.01700(18) 0.06499(10) 0.0342(5) Uani 1 1 d . . . C19 C 0.58714(12) -0.1116(2) 0.06108(11) 0.0416(5) Uani 1 1 d . . . C20 C 0.46634(14) -0.1472(3) 0.07173(19) 0.0824(10) Uani 1 1 d . . . H20A H 0.4728 -0.2078 0.1065 0.124 Uiso 1 1 calc R . . H20B H 0.4636 -0.1870 0.0284 0.124 Uiso 1 1 calc R . . H20C H 0.4237 -0.1026 0.0800 0.124 Uiso 1 1 calc R . . N1 N 0.60826(12) -0.1730(2) 0.24401(11) 0.0580(6) Uani 1 1 d . . . N2 N 0.63109(11) 0.07018(17) 0.25577(10) 0.0416(5) Uani 1 1 d . . . N3 N 0.63814(9) 0.06058(15) 0.11728(9) 0.0355(4) Uani 1 1 d . . . N4 N 0.81042(13) 0.0750(2) -0.01153(13) 0.0605(7) Uani 1 1 d . . . O1 O 0.62376(12) 0.04628(18) 0.36957(9) 0.0744(6) Uani 1 1 d . . . O2 O 0.59645(9) -0.21819(16) 0.05129(12) 0.0734(6) Uani 1 1 d . . . O3 O 0.52482(9) -0.06308(15) 0.07216(10) 0.0585(5) Uani 1 1 d . . . F1 F 0.44090(9) -0.16696(18) 0.41837(9) 0.0863(6) Uani 1 1 d . . . F2 F 0.47772(9) 0.00594(16) 0.38111(8) 0.0800(5) Uani 1 1 d . . . F3 F 0.53697(8) -0.09399(16) 0.45462(7) 0.0736(5) Uani 1 1 d . . . Cl1 Cl 0.70441(4) -0.11341(6) -0.04874(3) 0.0573(2) Uani 1 1 d . . . H1 H 0.6235(12) 0.032(2) 0.2183(12) 0.046(7) Uiso 1 1 d . . . H2 H 0.8431(15) 0.128(3) -0.0019(14) 0.072(10) Uiso 1 1 d . . . H7 H 0.8169(14) 0.022(3) -0.0439(14) 0.066(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0493(15) 0.0705(18) 0.0495(15) 0.0134(14) -0.0024(13) -0.0065(14) C2 0.0423(14) 0.0483(14) 0.0465(13) 0.0138(11) -0.0032(11) -0.0053(11) C3 0.0602(18) 0.0560(17) 0.0704(19) 0.0176(15) 0.0011(14) -0.0166(14) C4 0.080(2) 0.0427(15) 0.091(2) 0.0012(15) 0.0042(18) -0.0120(15) C5 0.081(2) 0.0498(17) 0.077(2) -0.0072(15) 0.0125(17) -0.0070(15) C6 0.0471(14) 0.0433(13) 0.0430(13) 0.0084(11) -0.0042(11) -0.0031(11) C7 0.0453(14) 0.0450(13) 0.0399(13) 0.0085(11) -0.0034(11) -0.0070(11) C8 0.0400(13) 0.0332(11) 0.0424(12) -0.0022(10) 0.0066(10) -0.0028(10) C9 0.0754(19) 0.0499(15) 0.0443(14) -0.0100(12) 0.0201(13) -0.0100(13) C10 0.084(2) 0.0499(15) 0.0591(17) -0.0246(13) 0.0183(15) -0.0159(15) C11 0.0631(17) 0.0375(13) 0.0682(18) -0.0108(12) 0.0144(14) -0.0149(12) C12 0.0495(15) 0.0395(12) 0.0502(14) -0.0016(11) 0.0123(11) -0.0081(11) C13 0.0332(12) 0.0349(11) 0.0385(12) -0.0017(9) 0.0053(9) -0.0037(9) C14 0.0373(12) 0.0313(11) 0.0339(11) 0.0029(9) 0.0009(9) 0.0005(9) C15 0.0407(13) 0.0387(12) 0.0418(12) 0.0006(10) 0.0085(11) -0.0066(10) C16 0.0442(13) 0.0390(12) 0.0353(11) 0.0045(9) 0.0114(10) 0.0018(10) C17 0.0449(13) 0.0335(11) 0.0299(10) 0.0005(9) 0.0016(10) 0.0045(10) C18 0.0349(12) 0.0315(11) 0.0364(11) 0.0007(9) -0.0006(9) 0.0032(9) C19 0.0411(14) 0.0402(13) 0.0434(13) -0.0050(10) 0.0012(10) 0.0016(11) C20 0.0386(16) 0.084(2) 0.124(3) -0.013(2) 0.0116(17) -0.0141(16) N1 0.0684(15) 0.0459(12) 0.0598(14) -0.0014(11) 0.0104(11) -0.0078(11) N2 0.0537(13) 0.0354(10) 0.0356(11) -0.0028(9) 0.0090(9) -0.0067(9) N3 0.0371(10) 0.0319(9) 0.0374(10) -0.0011(8) 0.0041(8) -0.0008(8) N4 0.0644(16) 0.0572(14) 0.0598(15) -0.0171(12) 0.0307(12) -0.0142(13) O1 0.1129(17) 0.0712(13) 0.0392(10) 0.0112(9) -0.0170(10) -0.0356(12) O2 0.0527(12) 0.0430(11) 0.1244(18) -0.0249(11) 0.0091(11) -0.0069(9) O3 0.0375(10) 0.0512(10) 0.0868(13) -0.0074(9) 0.0105(9) -0.0025(8) F1 0.0573(10) 0.1183(15) 0.0832(12) 0.0016(11) 0.0194(9) -0.0196(10) F2 0.0915(13) 0.0774(12) 0.0711(11) 0.0082(9) 0.0017(9) 0.0270(10) F3 0.0703(11) 0.1064(13) 0.0439(9) 0.0099(8) -0.0058(8) -0.0050(9) Cl1 0.0811(5) 0.0493(4) 0.0414(3) -0.0104(3) 0.0123(3) -0.0044(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F3 1.319(3) . ? C1 F2 1.331(3) . ? C1 F1 1.346(3) . ? C1 C2 1.500(4) . ? C2 C3 1.387(3) . ? C2 C6 1.396(3) . ? C3 C4 1.365(4) . ? C3 H3 0.9300 . ? C4 C5 1.372(4) . ? C4 H4 0.9300 . ? C5 N1 1.332(3) . ? C5 H5 0.9300 . ? C6 N1 1.334(3) . ? C6 C7 1.512(3) . ? C7 O1 1.215(3) . ? C7 N2 1.339(3) . ? C8 C9 1.391(3) . ? C8 C13 1.406(3) . ? C8 N2 1.407(3) . ? C9 C10 1.374(3) . ? C9 H9 0.9300 . ? C10 C11 1.367(4) . ? C10 H10 0.9300 . ? C11 C12 1.371(3) . ? C11 H11 0.9300 . ? C12 C13 1.391(3) . ? C12 H12 0.9300 . ? C13 C14 1.487(3) . ? C14 N3 1.348(3) . ? C14 C15 1.376(3) . ? C15 C16 1.394(3) . ? C15 H15 0.9300 . ? C16 N4 1.340(3) . ? C16 C17 1.408(3) . ? C17 C18 1.380(3) . ? C17 Cl1 1.728(2) . ? C18 N3 1.338(3) . ? C18 C19 1.498(3) . ? C19 O2 1.188(3) . ? C19 O3 1.317(3) . ? C20 O3 1.441(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N2 H1 0.86(2) . ? N4 H2 0.87(3) . ? N4 H7 0.87(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F3 C1 F2 107.4(2) . . ? F3 C1 F1 105.4(2) . . ? F2 C1 F1 106.0(2) . . ? F3 C1 C2 114.4(2) . . ? F2 C1 C2 112.6(2) . . ? F1 C1 C2 110.5(2) . . ? C3 C2 C6 117.4(2) . . ? C3 C2 C1 119.0(2) . . ? C6 C2 C1 123.4(2) . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 118.8(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 122.9(3) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? N1 C6 C2 122.5(2) . . ? N1 C6 C7 114.5(2) . . ? C2 C6 C7 123.0(2) . . ? O1 C7 N2 125.0(2) . . ? O1 C7 C6 121.3(2) . . ? N2 C7 C6 113.7(2) . . ? C9 C8 C13 119.3(2) . . ? C9 C8 N2 121.8(2) . . ? C13 C8 N2 118.93(19) . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 120.4(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.5(2) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C12 C13 122.0(2) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C12 C13 C8 117.94(19) . . ? C12 C13 C14 119.00(19) . . ? C8 C13 C14 123.01(18) . . ? N3 C14 C15 122.00(19) . . ? N3 C14 C13 117.67(18) . . ? C15 C14 C13 120.31(19) . . ? C14 C15 C16 121.3(2) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? N4 C16 C15 121.3(2) . . ? N4 C16 C17 122.6(2) . . ? C15 C16 C17 116.00(19) . . ? C18 C17 C16 119.41(19) . . ? C18 C17 Cl1 122.60(17) . . ? C16 C17 Cl1 117.99(16) . . ? N3 C18 C17 123.65(19) . . ? N3 C18 C19 114.26(18) . . ? C17 C18 C19 122.04(19) . . ? O2 C19 O3 123.5(2) . . ? O2 C19 C18 124.8(2) . . ? O3 C19 C18 111.69(19) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 N1 C6 118.2(2) . . ? C7 N2 C8 128.7(2) . . ? C7 N2 H1 115.8(16) . . ? C8 N2 H1 115.5(16) . . ? C18 N3 C14 117.62(18) . . ? C16 N4 H2 117.9(19) . . ? C16 N4 H7 122.0(18) . . ? H2 N4 H7 120(3) . . ? C19 O3 C20 116.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F3 C1 C2 C3 102.8(3) . . . . ? F2 C1 C2 C3 -134.2(2) . . . . ? F1 C1 C2 C3 -15.9(3) . . . . ? F3 C1 C2 C6 -80.8(3) . . . . ? F2 C1 C2 C6 42.3(3) . . . . ? F1 C1 C2 C6 160.6(2) . . . . ? C6 C2 C3 C4 -1.4(4) . . . . ? C1 C2 C3 C4 175.3(3) . . . . ? C2 C3 C4 C5 -3.3(4) . . . . ? C3 C4 C5 N1 4.3(5) . . . . ? C3 C2 C6 N1 5.7(4) . . . . ? C1 C2 C6 N1 -170.8(2) . . . . ? C3 C2 C6 C7 -171.8(2) . . . . ? C1 C2 C6 C7 11.7(4) . . . . ? N1 C6 C7 O1 -146.6(3) . . . . ? C2 C6 C7 O1 31.1(4) . . . . ? N1 C6 C7 N2 32.5(3) . . . . ? C2 C6 C7 N2 -149.8(2) . . . . ? C13 C8 C9 C10 4.1(4) . . . . ? N2 C8 C9 C10 -175.9(3) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C9 C10 C11 C12 -2.8(5) . . . . ? C10 C11 C12 C13 2.1(4) . . . . ? C11 C12 C13 C8 1.7(4) . . . . ? C11 C12 C13 C14 -175.7(2) . . . . ? C9 C8 C13 C12 -4.7(3) . . . . ? N2 C8 C13 C12 175.3(2) . . . . ? C9 C8 C13 C14 172.6(2) . . . . ? N2 C8 C13 C14 -7.4(3) . . . . ? C12 C13 C14 N3 -143.8(2) . . . . ? C8 C13 C14 N3 38.9(3) . . . . ? C12 C13 C14 C15 37.9(3) . . . . ? C8 C13 C14 C15 -139.4(2) . . . . ? N3 C14 C15 C16 0.4(3) . . . . ? C13 C14 C15 C16 178.6(2) . . . . ? C14 C15 C16 N4 -178.7(2) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? N4 C16 C17 C18 177.7(2) . . . . ? C15 C16 C17 C18 -1.2(3) . . . . ? N4 C16 C17 Cl1 -2.5(3) . . . . ? C15 C16 C17 Cl1 178.58(16) . . . . ? C16 C17 C18 N3 1.7(3) . . . . ? Cl1 C17 C18 N3 -178.06(16) . . . . ? C16 C17 C18 C19 -175.3(2) . . . . ? Cl1 C17 C18 C19 4.9(3) . . . . ? N3 C18 C19 O2 -133.8(3) . . . . ? C17 C18 C19 O2 43.4(3) . . . . ? N3 C18 C19 O3 44.0(3) . . . . ? C17 C18 C19 O3 -138.7(2) . . . . ? C4 C5 N1 C6 -0.2(4) . . . . ? C2 C6 N1 C5 -4.9(4) . . . . ? C7 C6 N1 C5 172.8(2) . . . . ? O1 C7 N2 C8 -2.2(4) . . . . ? C6 C7 N2 C8 178.7(2) . . . . ? C9 C8 N2 C7 -11.2(4) . . . . ? C13 C8 N2 C7 168.8(2) . . . . ? C17 C18 N3 C14 -1.1(3) . . . . ? C19 C18 N3 C14 176.18(18) . . . . ? C15 C14 N3 C18 0.0(3) . . . . ? C13 C14 N3 C18 -178.26(18) . . . . ? O2 C19 O3 C20 -0.2(4) . . . . ? C18 C19 O3 C20 -178.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.245 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.058