# Electronic Supplementary Material (ESI) for Chemical Communications # 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_ishida #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C21 H11 Cl5 F3 N3' _chemical_formula_moiety 'C21 H11 Cl5 F3 N3' _chemical_formula_weight 539.60 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.068(3) _cell_length_b 8.982(3) _cell_length_c 21.773(7) _cell_angle_alpha 90.0000 _cell_angle_beta 92.46(3) _cell_angle_gamma 90.0000 _cell_volume 2162.4(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 18232 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.45 _cell_measurement_temperature 133 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.390 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.090 _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080.00 _exptl_absorpt_coefficient_mu 0.711 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 133 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 4920 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 27.43 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # 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 4920 _reflns_number_gt 3559 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0930 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 4920 _refine_ls_number_parameters 297 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.610 _refine_diff_density_min -0.410 _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 0.003 0.002 ; 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 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.148 0.159 ; 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 0.00482(5) -0.31701(6) 0.44421(2) 0.02313(12) Uani 1.0 4 d . . . Cl(2) Cl 0.26555(5) -0.17995(6) 0.42797(2) 0.02430(13) Uani 1.0 4 d . . . Cl(3) Cl 0.32968(8) 0.03258(8) 0.85276(3) 0.0519(2) Uani 1.0 4 d . . . Cl(4) Cl 0.26232(6) 0.07690(8) 0.97827(3) 0.04688(19) Uani 1.0 4 d . . . Cl(5) Cl 0.49649(6) 0.17467(8) 0.94048(3) 0.04524(18) Uani 1.0 4 d . . . F(1) F 0.44452(11) -0.00681(15) 0.62362(5) 0.0268(3) Uani 1.0 4 d . . . F(2) F 0.41206(12) 0.19946(15) 0.57492(5) 0.0306(3) Uani 1.0 4 d . . . F(3) F 0.50708(11) 0.19992(17) 0.66318(6) 0.0333(4) Uani 1.0 4 d . . . N(1) N 0.00383(14) -0.01053(19) 0.64562(7) 0.0162(4) Uani 1.0 4 d . . . N(2) N 0.19715(14) 0.07856(18) 0.64054(7) 0.0148(4) Uani 1.0 4 d . . . N(3) N 0.18765(15) 0.34649(19) 0.79249(7) 0.0188(4) Uani 1.0 4 d . . . C(1) C 0.00281(18) -0.1610(3) 0.54975(8) 0.0177(4) Uani 1.0 4 d . . . C(2) C 0.06881(18) -0.1986(3) 0.49977(8) 0.0177(4) Uani 1.0 4 d . . . C(3) C 0.18582(18) -0.1401(3) 0.49332(8) 0.0182(4) Uani 1.0 4 d . . . C(4) C 0.24005(18) -0.0475(3) 0.53662(8) 0.0176(4) Uani 1.0 4 d . . . C(5) C 0.17383(17) -0.0116(3) 0.58821(8) 0.0153(4) Uani 1.0 4 d . . . C(6) C 0.05556(17) -0.0652(3) 0.59385(8) 0.0159(4) Uani 1.0 4 d . . . C(7) C 0.08770(17) 0.0766(3) 0.67235(8) 0.0152(4) Uani 1.0 4 d . . . C(8) C 0.07657(17) 0.1651(2) 0.72566(8) 0.0156(4) Uani 1.0 4 d . . . C(9) C 0.17501(17) 0.2485(3) 0.74448(8) 0.0158(4) Uani 1.0 4 d . . . C(10) C 0.29022(17) 0.2428(3) 0.71459(8) 0.0161(4) Uani 1.0 4 d . . . C(11) C 0.36953(18) 0.3412(3) 0.74920(9) 0.0221(5) Uani 1.0 4 d . . . C(12) C 0.30348(19) 0.4017(3) 0.79402(9) 0.0220(5) Uani 1.0 4 d . . . C(13) C 0.29865(17) 0.1549(3) 0.66308(8) 0.0157(4) Uani 1.0 4 d . . . C(14) C 0.41483(18) 0.1369(3) 0.63116(9) 0.0210(5) Uani 1.0 4 d . . . C(15) C -0.03982(17) 0.1686(3) 0.75803(8) 0.0170(4) Uani 1.0 4 d . . . C(16) C -0.13844(18) 0.2456(3) 0.73264(9) 0.0224(5) Uani 1.0 4 d . . . C(17) C -0.24543(19) 0.2535(3) 0.76401(10) 0.0286(5) Uani 1.0 4 d . . . C(18) C -0.2544(2) 0.1828(3) 0.82044(10) 0.0290(5) Uani 1.0 4 d . . . C(19) C -0.1565(2) 0.1060(3) 0.84555(10) 0.0289(5) Uani 1.0 4 d . . . C(20) C -0.0483(2) 0.0994(3) 0.81519(9) 0.0233(5) Uani 1.0 4 d . . . C(21) C 0.3820(3) 0.0398(3) 0.93003(10) 0.0302(5) Uani 1.0 4 d . . . H(1) H -0.0764 -0.1991 0.5541 0.0213 Uiso 1.0 4 calc R . . H(2) H 0.3191 -0.0094 0.5318 0.0211 Uiso 1.0 4 calc R . . H(3) H -0.1331 0.2930 0.6939 0.0269 Uiso 1.0 4 calc R . . H(4) H -0.3125 0.3073 0.7468 0.0343 Uiso 1.0 4 calc R . . H(5) H -0.3276 0.1875 0.8416 0.0348 Uiso 1.0 4 calc R . . H(6) H -0.1628 0.0569 0.8839 0.0347 Uiso 1.0 4 calc R . . H(7) H 0.0194 0.0482 0.8333 0.0280 Uiso 1.0 4 calc R . . H(8) H 0.4522 0.3603 0.7421 0.0265 Uiso 1.0 4 calc R . . H(9) H 0.3336 0.4734 0.8229 0.0264 Uiso 1.0 4 calc R . . H(11) H 0.424(3) -0.057(3) 0.9398(11) 0.035(7) Uiso 1.0 4 d . . . H(10) H 0.117(3) 0.395(4) 0.8147(11) 0.039(8) Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(1) 0.0246(3) 0.0249(3) 0.0200(3) -0.0028(2) 0.00133(18) -0.0060(2) Cl(2) 0.0233(3) 0.0323(3) 0.0179(3) 0.0008(3) 0.00840(18) -0.0051(2) Cl(3) 0.0791(6) 0.0388(4) 0.0360(4) -0.0004(4) -0.0179(4) 0.0042(3) Cl(4) 0.0305(4) 0.0469(4) 0.0644(5) -0.0018(3) 0.0145(3) -0.0101(4) Cl(5) 0.0440(4) 0.0542(5) 0.0383(4) -0.0203(4) 0.0113(3) -0.0018(3) F(1) 0.0179(6) 0.0317(7) 0.0309(7) 0.0094(6) 0.0015(5) -0.0074(6) F(2) 0.0299(7) 0.0385(8) 0.0245(6) -0.0070(7) 0.0143(6) 0.0032(6) F(3) 0.0113(6) 0.0506(9) 0.0383(7) -0.0056(6) 0.0062(5) -0.0203(7) N(1) 0.0140(8) 0.0200(9) 0.0148(7) -0.0011(7) 0.0043(6) 0.0003(7) N(2) 0.0107(8) 0.0190(9) 0.0149(7) 0.0017(7) 0.0043(6) 0.0001(7) N(3) 0.0135(8) 0.0223(9) 0.0206(8) 0.0012(7) 0.0027(6) -0.0044(7) C(1) 0.0150(9) 0.0196(10) 0.0188(9) -0.0015(8) 0.0027(7) 0.0008(8) C(2) 0.0189(10) 0.0180(10) 0.0162(9) -0.0013(9) -0.0005(7) -0.0022(8) C(3) 0.0169(10) 0.0217(10) 0.0162(9) 0.0037(8) 0.0046(8) 0.0007(8) C(4) 0.0130(9) 0.0236(10) 0.0165(9) 0.0016(8) 0.0048(7) 0.0019(8) C(5) 0.0150(10) 0.0176(10) 0.0134(9) 0.0000(8) 0.0010(7) -0.0001(8) C(6) 0.0124(9) 0.0197(10) 0.0159(9) 0.0008(8) 0.0038(7) 0.0026(8) C(7) 0.0101(9) 0.0207(10) 0.0153(8) 0.0012(8) 0.0050(7) 0.0041(8) C(8) 0.0137(9) 0.0188(10) 0.0148(9) 0.0021(8) 0.0043(7) 0.0006(8) C(9) 0.0135(9) 0.0192(10) 0.0147(9) 0.0024(8) 0.0026(7) 0.0004(8) C(10) 0.0104(9) 0.0188(10) 0.0194(9) 0.0022(8) 0.0032(7) 0.0023(8) C(11) 0.0145(10) 0.0253(11) 0.0268(10) -0.0011(9) 0.0038(8) -0.0037(9) C(12) 0.0168(10) 0.0256(11) 0.0236(10) -0.0013(9) 0.0004(8) -0.0049(9) C(13) 0.0113(9) 0.0189(10) 0.0172(9) 0.0004(8) 0.0031(7) 0.0010(8) C(14) 0.0129(10) 0.0269(11) 0.0235(10) -0.0005(9) 0.0055(8) -0.0048(9) C(15) 0.0135(9) 0.0200(10) 0.0181(9) -0.0030(8) 0.0054(7) -0.0031(8) C(16) 0.0168(10) 0.0298(12) 0.0209(10) -0.0009(9) 0.0030(8) -0.0009(9) C(17) 0.0151(11) 0.0355(13) 0.0352(12) 0.0028(10) 0.0027(9) -0.0061(11) C(18) 0.0192(11) 0.0360(13) 0.0329(12) -0.0082(11) 0.0143(9) -0.0104(10) C(19) 0.0295(12) 0.0355(13) 0.0227(10) -0.0058(11) 0.0118(9) -0.0006(10) C(20) 0.0208(11) 0.0283(11) 0.0211(10) -0.0009(9) 0.0057(8) -0.0002(9) C(21) 0.0324(13) 0.0290(12) 0.0291(11) -0.0003(11) 0.0013(10) 0.0010(10) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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 Cl(1) C(2) 1.738(2) yes . . Cl(2) C(3) 1.743(2) yes . . Cl(3) C(21) 1.757(3) yes . . Cl(4) C(21) 1.757(3) yes . . Cl(5) C(21) 1.761(3) yes . . F(1) C(14) 1.344(3) yes . . F(2) C(14) 1.346(3) yes . . F(3) C(14) 1.337(3) yes . . N(1) C(6) 1.377(3) yes . . N(1) C(7) 1.329(3) yes . . N(2) C(5) 1.412(3) yes . . N(2) C(7) 1.421(3) yes . . N(2) C(13) 1.388(3) yes . . N(3) C(9) 1.369(3) yes . . N(3) C(12) 1.374(3) yes . . C(1) C(2) 1.379(3) yes . . C(1) C(6) 1.398(3) yes . . C(2) C(3) 1.410(3) yes . . C(3) C(4) 1.376(3) yes . . C(4) C(5) 1.405(3) yes . . C(5) C(6) 1.405(3) yes . . C(7) C(8) 1.416(3) yes . . C(8) C(9) 1.370(3) yes . . C(8) C(15) 1.495(3) yes . . C(9) C(10) 1.457(3) yes . . C(10) C(11) 1.436(3) yes . . C(10) C(13) 1.378(3) yes . . C(11) C(12) 1.358(3) yes . . C(13) C(14) 1.496(3) yes . . C(15) C(16) 1.387(3) yes . . C(15) C(20) 1.398(3) yes . . C(16) C(17) 1.394(3) yes . . C(17) C(18) 1.390(4) yes . . C(18) C(19) 1.378(4) yes . . C(19) C(20) 1.394(4) yes . . N(3) H(10) 1.03(3) no . . C(1) H(1) 0.950 no . . C(4) H(2) 0.950 no . . C(11) H(8) 0.950 no . . C(12) H(9) 0.950 no . . C(16) H(3) 0.950 no . . C(17) H(4) 0.950 no . . C(18) H(5) 0.950 no . . C(19) H(6) 0.950 no . . C(20) H(7) 0.950 no . . C(21) H(11) 1.00(3) 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(6) N(1) C(7) 105.16(16) yes . . . C(5) N(2) C(7) 104.84(15) yes . . . C(5) N(2) C(13) 133.29(16) yes . . . C(7) N(2) C(13) 121.86(16) yes . . . C(9) N(3) C(12) 108.38(17) yes . . . C(2) C(1) C(6) 118.25(18) yes . . . Cl(1) C(2) C(1) 119.05(16) yes . . . Cl(1) C(2) C(3) 120.48(15) yes . . . C(1) C(2) C(3) 120.47(18) yes . . . Cl(2) C(3) C(2) 120.26(15) yes . . . Cl(2) C(3) C(4) 117.53(16) yes . . . C(2) C(3) C(4) 122.19(18) yes . . . C(3) C(4) C(5) 117.36(18) yes . . . N(2) C(5) C(4) 133.88(18) yes . . . N(2) C(5) C(6) 105.36(16) yes . . . C(4) C(5) C(6) 120.72(17) yes . . . N(1) C(6) C(1) 127.29(18) yes . . . N(1) C(6) C(5) 111.76(17) yes . . . C(1) C(6) C(5) 120.95(17) yes . . . N(1) C(7) N(2) 112.81(16) yes . . . N(1) C(7) C(8) 127.26(18) yes . . . N(2) C(7) C(8) 119.90(17) yes . . . C(7) C(8) C(9) 117.11(18) yes . . . C(7) C(8) C(15) 120.35(17) yes . . . C(9) C(8) C(15) 122.51(17) yes . . . N(3) C(9) C(8) 129.32(18) yes . . . N(3) C(9) C(10) 107.50(16) yes . . . C(8) C(9) C(10) 123.17(17) yes . . . C(9) C(10) C(11) 105.72(16) yes . . . C(9) C(10) C(13) 118.33(17) yes . . . C(11) C(10) C(13) 135.93(19) yes . . . C(10) C(11) C(12) 106.71(18) yes . . . N(3) C(12) C(11) 111.64(18) yes . . . N(2) C(13) C(10) 119.27(17) yes . . . N(2) C(13) C(14) 118.77(17) yes . . . C(10) C(13) C(14) 121.96(18) yes . . . F(1) C(14) F(2) 106.60(16) yes . . . F(1) C(14) F(3) 106.55(16) yes . . . F(1) C(14) C(13) 112.31(17) yes . . . F(2) C(14) F(3) 106.56(17) yes . . . F(2) C(14) C(13) 113.02(17) yes . . . F(3) C(14) C(13) 111.38(17) yes . . . C(8) C(15) C(16) 120.13(17) yes . . . C(8) C(15) C(20) 120.15(18) yes . . . C(16) C(15) C(20) 119.67(19) yes . . . C(15) C(16) C(17) 120.03(19) yes . . . C(16) C(17) C(18) 120.3(2) yes . . . C(17) C(18) C(19) 119.7(2) yes . . . C(18) C(19) C(20) 120.7(2) yes . . . C(15) C(20) C(19) 119.7(2) yes . . . Cl(3) C(21) Cl(4) 110.72(14) yes . . . Cl(3) C(21) Cl(5) 110.78(14) yes . . . Cl(4) C(21) Cl(5) 110.43(14) yes . . . C(9) N(3) H(10) 125.1(15) no . . . C(12) N(3) H(10) 124.1(16) no . . . C(2) C(1) H(1) 120.878 no . . . C(6) C(1) H(1) 120.875 no . . . C(3) C(4) H(2) 121.323 no . . . C(5) C(4) H(2) 121.314 no . . . C(10) C(11) H(8) 126.646 no . . . C(12) C(11) H(8) 126.639 no . . . N(3) C(12) H(9) 124.177 no . . . C(11) C(12) H(9) 124.181 no . . . C(15) C(16) H(3) 119.984 no . . . C(17) C(16) H(3) 119.986 no . . . C(16) C(17) H(4) 119.864 no . . . C(18) C(17) H(4) 119.869 no . . . C(17) C(18) H(5) 120.163 no . . . C(19) C(18) H(5) 120.164 no . . . C(18) C(19) H(6) 119.677 no . . . C(20) C(19) H(6) 119.670 no . . . C(15) C(20) H(7) 120.147 no . . . C(19) C(20) H(7) 120.166 no . . . Cl(3) C(21) H(11) 107.7(14) no . . . Cl(4) C(21) H(11) 113.0(15) no . . . Cl(5) C(21) H(11) 104.0(16) 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(6) N(1) C(7) N(2) -1.8(2) no . . . . C(6) N(1) C(7) C(8) 176.56(17) no . . . . C(7) N(1) C(6) C(1) -179.12(17) no . . . . C(7) N(1) C(6) C(5) 0.1(2) no . . . . C(5) N(2) C(7) N(1) 2.7(2) no . . . . C(5) N(2) C(7) C(8) -175.74(15) no . . . . C(7) N(2) C(5) C(4) 175.11(18) no . . . . C(7) N(2) C(5) C(6) -2.44(18) no . . . . C(5) N(2) C(13) C(10) 175.82(17) no . . . . C(5) N(2) C(13) C(14) -5.2(3) no . . . . C(13) N(2) C(5) C(4) -6.7(4) no . . . . C(13) N(2) C(5) C(6) 175.75(18) no . . . . C(7) N(2) C(13) C(10) -6.2(3) no . . . . C(7) N(2) C(13) C(14) 172.70(15) no . . . . C(13) N(2) C(7) N(1) -175.71(15) no . . . . C(13) N(2) C(7) C(8) 5.8(3) no . . . . C(9) N(3) C(12) C(11) -1.3(3) no . . . . C(12) N(3) C(9) C(8) 178.98(17) no . . . . C(12) N(3) C(9) C(10) 0.1(2) no . . . . C(2) C(1) C(6) N(1) 177.66(17) no . . . . C(2) C(1) C(6) C(5) -1.5(3) no . . . . C(6) C(1) C(2) Cl(1) -179.77(15) no . . . . C(6) C(1) C(2) C(3) -0.8(3) no . . . . Cl(1) C(2) C(3) Cl(2) 2.5(3) no . . . . Cl(1) C(2) C(3) C(4) -179.25(13) no . . . . C(1) C(2) C(3) Cl(2) -176.48(15) no . . . . C(1) C(2) C(3) C(4) 1.8(3) no . . . . Cl(2) C(3) C(4) C(5) 177.87(12) no . . . . C(2) C(3) C(4) C(5) -0.4(3) no . . . . C(3) C(4) C(5) N(2) -179.12(18) no . . . . C(3) C(4) C(5) C(6) -1.9(3) no . . . . N(2) C(5) C(6) N(1) 1.5(2) no . . . . N(2) C(5) C(6) C(1) -179.17(15) no . . . . C(4) C(5) C(6) N(1) -176.40(16) no . . . . C(4) C(5) C(6) C(1) 2.9(3) no . . . . N(1) C(7) C(8) C(9) -178.96(17) no . . . . N(1) C(7) C(8) C(15) -0.7(3) no . . . . N(2) C(7) C(8) C(9) -0.7(3) no . . . . N(2) C(7) C(8) C(15) 177.53(14) no . . . . C(7) C(8) C(9) N(3) 177.48(17) no . . . . C(7) C(8) C(9) C(10) -3.7(3) no . . . . C(7) C(8) C(15) C(16) -74.0(3) no . . . . C(7) C(8) C(15) C(20) 108.6(2) no . . . . C(9) C(8) C(15) C(16) 104.2(2) no . . . . C(9) C(8) C(15) C(20) -73.2(3) no . . . . C(15) C(8) C(9) N(3) -0.7(3) no . . . . C(15) C(8) C(9) C(10) 178.04(15) no . . . . N(3) C(9) C(10) C(11) 1.06(19) no . . . . N(3) C(9) C(10) C(13) -177.66(15) no . . . . C(8) C(9) C(10) C(11) -177.95(16) no . . . . C(8) C(9) C(10) C(13) 3.3(3) no . . . . C(9) C(10) C(11) C(12) -1.8(2) no . . . . C(9) C(10) C(13) N(2) 1.8(3) no . . . . C(9) C(10) C(13) C(14) -177.15(15) no . . . . C(11) C(10) C(13) N(2) -176.5(2) no . . . . C(11) C(10) C(13) C(14) 4.6(4) no . . . . C(13) C(10) C(11) C(12) 176.6(2) no . . . . C(10) C(11) C(12) N(3) 1.9(3) no . . . . N(2) C(13) C(14) F(1) -51.7(3) no . . . . N(2) C(13) C(14) F(2) 68.9(3) no . . . . N(2) C(13) C(14) F(3) -171.17(15) no . . . . C(10) C(13) C(14) F(1) 127.17(19) no . . . . C(10) C(13) C(14) F(2) -112.2(2) no . . . . C(10) C(13) C(14) F(3) 7.7(3) no . . . . C(8) C(15) C(16) C(17) -177.58(16) no . . . . C(8) C(15) C(20) C(19) 178.71(16) no . . . . C(16) C(15) C(20) C(19) 1.3(3) no . . . . C(20) C(15) C(16) C(17) -0.2(3) no . . . . C(15) C(16) C(17) C(18) -0.8(4) no . . . . C(16) C(17) C(18) C(19) 0.6(4) no . . . . C(17) C(18) C(19) C(20) 0.6(4) no . . . . C(18) C(19) C(20) C(15) -1.5(4) no . . . . 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) Cl(2) 3.1710(11) no . . F(1) N(2) 2.882(3) no . . F(1) C(4) 2.911(3) no . . F(1) C(5) 3.062(3) no . . F(1) C(10) 3.487(3) no . . F(2) N(2) 3.028(3) no . . F(2) C(4) 3.017(3) no . . F(2) C(5) 3.270(3) no . . F(2) C(10) 3.401(3) no . . F(3) C(10) 2.719(3) no . . F(3) C(11) 2.771(3) no . . N(1) C(13) 3.591(3) no . . N(1) C(15) 2.985(3) no . . N(1) C(16) 3.408(3) no . . N(2) C(1) 3.578(3) no . . N(2) C(9) 2.749(3) no . . N(3) C(13) 3.565(3) no . . N(3) C(15) 3.048(3) no . . N(3) C(20) 3.478(3) no . . C(1) C(4) 2.843(3) no . . C(1) C(7) 3.514(3) no . . C(2) C(5) 2.773(3) no . . C(3) C(6) 2.755(3) no . . C(4) C(13) 3.340(3) no . . C(4) C(14) 3.222(3) no . . C(5) C(8) 3.593(3) no . . C(5) C(14) 3.091(3) no . . C(6) C(8) 3.537(3) no . . C(7) C(10) 2.814(3) no . . C(7) C(16) 3.252(3) no . . C(7) C(20) 3.519(3) no . . C(8) C(12) 3.567(3) no . . C(8) C(13) 2.862(3) no . . C(9) C(16) 3.468(3) no . . C(9) C(20) 3.255(3) no . . C(11) C(14) 3.215(3) no . . C(15) C(18) 2.789(3) no . . C(16) C(19) 2.775(3) no . . C(17) C(20) 2.776(4) no . . Cl(1) Cl(4) 3.5954(13) no . 2_546 Cl(1) N(1) 3.5317(19) no . 3_556 Cl(1) N(2) 3.5546(18) no . 3_556 Cl(1) C(6) 3.588(3) no . 3_556 Cl(1) C(7) 3.454(2) no . 3_556 Cl(2) F(2) 3.5758(18) no . 3_656 Cl(2) F(3) 3.2760(17) no . 3_656 Cl(2) C(21) 3.479(3) no . 4_544 Cl(3) F(3) 3.5164(19) no . 2_646 Cl(3) N(3) 3.459(2) no . . Cl(3) C(9) 3.450(2) no . . Cl(3) C(10) 3.563(2) no . . Cl(3) C(12) 3.561(3) no . . Cl(4) Cl(1) 3.5954(13) no . 2_556 Cl(4) F(2) 3.3032(16) no . 4_555 Cl(5) F(1) 3.2613(17) no . 2_656 Cl(5) F(2) 3.3097(16) no . 4_555 F(1) Cl(5) 3.2613(17) no . 2_646 F(1) C(12) 3.353(3) no . 2_646 F(2) Cl(2) 3.5758(18) no . 3_656 F(2) Cl(4) 3.3032(16) no . 4_554 F(2) Cl(5) 3.3097(16) no . 4_554 F(3) Cl(2) 3.2760(17) no . 3_656 F(3) Cl(3) 3.5164(19) no . 2_656 F(3) C(12) 3.503(3) no . 2_646 F(3) C(17) 3.470(3) no . 1_655 N(1) Cl(1) 3.5317(19) no . 3_556 N(1) N(3) 2.864(3) no . 2_546 N(1) C(15) 3.577(3) no . 2_546 N(2) Cl(1) 3.5546(18) no . 3_556 N(3) Cl(3) 3.459(2) no . . N(3) N(1) 2.864(3) no . 2_556 N(3) C(15) 3.479(3) no . 2_556 N(3) C(20) 3.568(3) no . 2_556 C(1) C(2) 3.486(3) no . 3_556 C(1) C(3) 3.519(3) no . 3_556 C(1) C(19) 3.484(3) no . 2_546 C(2) C(1) 3.486(3) no . 3_556 C(2) C(6) 3.380(3) no . 3_556 C(3) C(1) 3.519(3) no . 3_556 C(5) C(18) 3.483(3) no . 2_546 C(6) Cl(1) 3.588(3) no . 3_556 C(6) C(2) 3.380(3) no . 3_556 C(6) C(19) 3.403(4) no . 2_546 C(7) Cl(1) 3.454(2) no . 3_556 C(9) Cl(3) 3.450(2) no . . C(10) Cl(3) 3.563(2) no . . C(12) Cl(3) 3.561(3) no . . C(12) F(1) 3.353(3) no . 2_656 C(12) F(3) 3.503(3) no . 2_656 C(12) C(17) 3.453(4) no . 2_556 C(12) C(18) 3.573(4) no . 2_556 C(15) N(1) 3.577(3) no . 2_556 C(15) N(3) 3.479(3) no . 2_546 C(17) F(3) 3.470(3) no . 1_455 C(17) C(12) 3.453(4) no . 2_546 C(18) C(5) 3.483(3) no . 2_556 C(18) C(12) 3.573(4) no . 2_546 C(19) C(1) 3.484(3) no . 2_556 C(19) C(6) 3.403(4) no . 2_556 C(20) N(3) 3.568(3) no . 2_546 C(21) Cl(2) 3.479(3) no . 4_545 Cl(1) H(1) 2.8001 no . . Cl(2) H(2) 2.7746 no . . F(1) H(2) 2.3838 no . . F(2) H(2) 2.3178 no . . F(3) H(8) 2.3423 no . . N(1) H(1) 2.7342 no . . N(1) H(3) 3.3120 no . . N(2) H(2) 2.8850 no . . N(3) H(7) 3.4018 no . . N(3) H(8) 3.1729 no . . C(2) H(2) 3.2999 no . . C(3) H(1) 3.2843 no . . C(5) H(1) 3.2992 no . . C(6) H(2) 3.3052 no . . C(7) H(3) 3.1727 no . . C(8) H(3) 2.6546 no . . C(8) H(7) 2.6677 no . . C(8) H(10) 2.85(3) no . . C(9) H(3) 3.5608 no . . C(9) H(7) 3.1971 no . . C(9) H(8) 3.2306 no . . C(9) H(9) 3.1337 no . . C(10) H(9) 3.1594 no . . C(10) H(10) 3.26(3) no . . C(11) H(10) 3.23(3) no . . C(13) H(2) 3.2326 no . . C(13) H(8) 3.0002 no . . C(14) H(2) 2.7072 no . . C(14) H(8) 3.1535 no . . C(15) H(4) 3.2648 no . . C(15) H(6) 3.2702 no . . C(15) H(10) 2.91(3) no . . C(16) H(5) 3.2721 no . . C(16) H(7) 3.2661 no . . C(16) H(10) 3.54(3) no . . C(17) H(6) 3.2505 no . . C(18) H(3) 3.2703 no . . C(18) H(7) 3.2633 no . . C(19) H(4) 3.2498 no . . C(20) H(3) 3.2666 no . . C(20) H(5) 3.2657 no . . C(20) H(10) 3.22(3) no . . H(3) H(4) 2.3418 no . . H(4) H(5) 2.3405 no . . H(5) H(6) 2.3254 no . . H(6) H(7) 2.3417 no . . H(7) H(10) 3.3264 no . . H(8) H(9) 2.4585 no . . H(9) H(10) 2.4954 no . . Cl(1) H(3) 3.3859 no . 3_556 Cl(1) H(6) 3.0983 no . 4_544 Cl(1) H(7) 3.1950 no . 4_544 Cl(2) H(3) 3.1441 no . 3_556 Cl(2) H(9) 3.0649 no . 4_554 Cl(2) H(11) 2.95(3) no . 4_544 Cl(3) H(3) 3.1945 no . 2_546 Cl(3) H(4) 2.9647 no . 2_546 Cl(3) H(7) 3.4448 no . . Cl(3) H(8) 3.5940 no . 2_646 Cl(4) H(1) 2.9417 no . 2_556 Cl(4) H(6) 3.4557 no . 3_557 Cl(5) H(2) 3.5321 no . 2_656 Cl(5) H(5) 2.9666 no . 1_655 Cl(5) H(11) 2.91(3) no . 3_657 F(1) H(5) 3.1415 no . 2_546 F(1) H(8) 3.3154 no . 2_646 F(1) H(9) 2.6781 no . 2_646 F(2) H(11) 2.87(3) no . 2_656 F(3) H(4) 2.8136 no . 1_655 F(3) H(9) 2.7008 no . 2_646 F(3) H(11) 3.25(3) no . 2_656 N(1) H(10) 1.83(3) no . 2_546 C(1) H(6) 3.3794 no . 2_546 C(1) H(10) 3.33(3) no . 2_546 C(2) H(6) 3.4767 no . 2_546 C(3) H(1) 3.4216 no . 3_556 C(4) H(1) 3.4323 no . 3_556 C(5) H(5) 3.5089 no . 2_546 C(6) H(10) 2.84(3) no . 2_546 C(7) H(10) 2.82(3) no . 2_546 C(8) H(10) 3.33(3) no . 2_546 C(11) H(4) 3.5349 no . 1_655 C(14) H(9) 3.2667 no . 2_646 C(15) H(10) 3.03(3) no . 2_546 C(16) H(7) 3.3680 no . 2_556 C(16) H(9) 3.4473 no . 2_546 C(16) H(10) 3.33(3) no . 2_546 C(17) H(8) 3.4944 no . 1_455 C(17) H(9) 3.2715 no . 2_546 C(20) H(1) 3.5973 no . 2_556 C(20) H(3) 3.4166 no . 2_546 C(20) H(10) 3.43(3) no . 2_546 C(21) H(11) 3.48(3) no . 3_657 H(1) Cl(4) 2.9417 no . 2_546 H(1) C(3) 3.4216 no . 3_556 H(1) C(4) 3.4323 no . 3_556 H(1) C(20) 3.5973 no . 2_546 H(1) H(7) 3.3807 no . 2_546 H(1) H(10) 3.0309 no . 2_546 H(2) Cl(5) 3.5321 no . 2_646 H(3) Cl(1) 3.3859 no . 3_556 H(3) Cl(2) 3.1441 no . 3_556 H(3) Cl(3) 3.1945 no . 2_556 H(3) C(20) 3.4166 no . 2_556 H(3) H(7) 2.6920 no . 2_556 H(3) H(10) 3.5860 no . 2_546 H(4) Cl(3) 2.9647 no . 2_556 H(4) F(3) 2.8136 no . 1_455 H(4) C(11) 3.5349 no . 1_455 H(4) H(8) 2.6449 no . 1_455 H(4) H(9) 3.3641 no . 2_546 H(5) Cl(5) 2.9666 no . 1_455 H(5) F(1) 3.1415 no . 2_556 H(5) C(5) 3.5089 no . 2_556 H(5) H(8) 3.5479 no . 1_455 H(6) Cl(1) 3.0983 no . 4_545 H(6) Cl(4) 3.4557 no . 3_557 H(6) C(1) 3.3794 no . 2_556 H(6) C(2) 3.4767 no . 2_556 H(7) Cl(1) 3.1950 no . 4_545 H(7) Cl(3) 3.4448 no . . H(7) C(16) 3.3680 no . 2_546 H(7) H(1) 3.3807 no . 2_556 H(7) H(3) 2.6920 no . 2_546 H(8) Cl(3) 3.5940 no . 2_656 H(8) F(1) 3.3154 no . 2_656 H(8) C(17) 3.4944 no . 1_655 H(8) H(4) 2.6449 no . 1_655 H(8) H(5) 3.5479 no . 1_655 H(9) Cl(2) 3.0649 no . 4_555 H(9) F(1) 2.6781 no . 2_656 H(9) F(3) 2.7008 no . 2_656 H(9) C(14) 3.2667 no . 2_656 H(9) C(16) 3.4473 no . 2_556 H(9) C(17) 3.2715 no . 2_556 H(9) H(4) 3.3641 no . 2_556 H(11) Cl(2) 2.95(3) no . 4_545 H(11) Cl(5) 2.91(3) no . 3_657 H(11) F(2) 2.87(3) no . 2_646 H(11) F(3) 3.25(3) no . 2_646 H(11) C(21) 3.48(3) no . 3_657 H(11) H(11) 3.22(4) no . 3_657 H(10) N(1) 1.83(3) no . 2_556 H(10) C(1) 3.33(3) no . 2_556 H(10) C(6) 2.84(3) no . 2_556 H(10) C(7) 2.82(3) no . 2_556 H(10) C(8) 3.33(3) no . 2_556 H(10) C(15) 3.03(3) no . 2_556 H(10) C(16) 3.33(3) no . 2_556 H(10) C(20) 3.43(3) no . 2_556 H(10) H(1) 3.0309 no . 2_556 H(10) H(3) 3.5860 no . 2_556 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N(3) H(10) N(1) . . 2_556 2.864(3) 1.03(3) 1.83(3) 177(3) 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 940145' ####################################################################### # # 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_ishida #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H12 Cl2 F3 N3' _chemical_formula_moiety 'C24 H12 Cl2 F3 N3' _chemical_formula_weight 470.28 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 8.1864(12) _cell_length_b 10.575(2) _cell_length_c 22.441(4) _cell_angle_alpha 90.0000 _cell_angle_beta 91.640(9) _cell_angle_gamma 90.0000 _cell_volume 1942.0(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 29425 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.46 _cell_measurement_temperature 133 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952.00 _exptl_absorpt_coefficient_mu 0.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 0.981 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 133 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type ? _diffrn_reflns_number 31123 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # 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 4445 _reflns_number_gt 3973 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0819 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 4445 _refine_ls_number_parameters 293 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0367P)^2^+1.3339P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.390 _refine_diff_density_min -0.250 _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 0.003 0.002 ; 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 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.148 0.159 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.017 0.010 ; 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 Cl1 Cl 0.24896(5) -0.38012(4) 0.502994(16) 0.02790(10) Uani 1.0 4 d . . . Cl2 Cl 0.56215(5) -0.28271(4) 0.437168(15) 0.02499(10) Uani 1.0 4 d . . . F1 F 0.92081(10) -0.07981(8) 0.57957(4) 0.02122(18) Uani 1.0 4 d . . . F2 F 0.87683(12) 0.07839(9) 0.52016(4) 0.0270(2) Uani 1.0 4 d . . . F3 F 1.05327(11) 0.09251(9) 0.59294(4) 0.0293(3) Uani 1.0 4 d . . . N1 N 0.40183(14) -0.04870(11) 0.66508(5) 0.0172(3) Uani 1.0 4 d . . . N2 N 0.63452(14) 0.01975(11) 0.62129(5) 0.0158(3) Uani 1.0 4 d . . . N3 N 0.73466(15) 0.30582(12) 0.73964(5) 0.0173(3) Uani 1.0 4 d . . . C1 C 0.32651(17) -0.21086(14) 0.58864(6) 0.0186(3) Uani 1.0 4 d . . . C2 C 0.37078(18) -0.26270(14) 0.53489(6) 0.0198(3) Uani 1.0 4 d . . . C3 C 0.50960(18) -0.21935(14) 0.50533(6) 0.0191(3) Uani 1.0 4 d . . . C4 C 0.60817(17) -0.12432(14) 0.52898(6) 0.0186(3) Uani 1.0 4 d . . . C5 C 0.56662(17) -0.07501(13) 0.58418(6) 0.0165(3) Uani 1.0 4 d . . . C6 C 0.42534(17) -0.11525(13) 0.61333(6) 0.0170(3) Uani 1.0 4 d . . . C7 C 0.52511(16) 0.03308(13) 0.66875(6) 0.0159(3) Uani 1.0 4 d . . . C8 C 0.55205(16) 0.12798(13) 0.71230(6) 0.0160(3) Uani 1.0 4 d . . . C9 C 0.44354(16) 0.13963(13) 0.76433(6) 0.0157(3) Uani 1.0 4 d . . . C10 C 0.46104(17) 0.05659(14) 0.81235(6) 0.0182(3) Uani 1.0 4 d . . . C11 C 0.36314(18) 0.06925(15) 0.86178(6) 0.0209(3) Uani 1.0 4 d . . . C12 C 0.24707(18) 0.16448(15) 0.86344(6) 0.0209(3) Uani 1.0 4 d . . . C13 C 0.22797(18) 0.24716(14) 0.81548(6) 0.0212(3) Uani 1.0 4 d . . . C14 C 0.32557(17) 0.23512(14) 0.76616(6) 0.0191(3) Uani 1.0 4 d . . . C15 C 0.68195(16) 0.20813(13) 0.70401(6) 0.0162(3) Uani 1.0 4 d . . . C16 C 0.79626(16) 0.19283(14) 0.65599(6) 0.0166(3) Uani 1.0 4 d . . . C17 C 0.77570(17) 0.09240(13) 0.61805(6) 0.0167(3) Uani 1.0 4 d . . . C18 C 0.90631(17) 0.04670(14) 0.57742(6) 0.0193(3) Uani 1.0 4 d . . . C19 C 0.91492(17) 0.29563(14) 0.66313(6) 0.0174(3) Uani 1.0 4 d . . . C20 C 0.87089(17) 0.36147(14) 0.71510(6) 0.0173(3) Uani 1.0 4 d . . . C21 C 0.95325(17) 0.46901(14) 0.73525(6) 0.0200(3) Uani 1.0 4 d . . . C22 C 1.07840(18) 0.51413(15) 0.70065(7) 0.0223(3) Uani 1.0 4 d . . . C23 C 1.11935(18) 0.45399(15) 0.64749(7) 0.0222(3) Uani 1.0 4 d . . . C24 C 1.03951(17) 0.34558(15) 0.62837(6) 0.0203(3) Uani 1.0 4 d . . . H1 H 0.2319 -0.2393 0.6082 0.0224 Uiso 1.0 4 calc R . . H2 H 0.7002 -0.0940 0.5085 0.0223 Uiso 1.0 4 calc R . . H3 H 0.5402 -0.0090 0.8114 0.0219 Uiso 1.0 4 calc R . . H4 H 0.3760 0.0125 0.8944 0.0250 Uiso 1.0 4 calc R . . H5 H 0.1807 0.1733 0.8972 0.0251 Uiso 1.0 4 calc R . . H6 H 0.1479 0.3121 0.8165 0.0255 Uiso 1.0 4 calc R . . H7 H 0.3121 0.2919 0.7336 0.0229 Uiso 1.0 4 calc R . . H8 H 0.682(3) 0.340(2) 0.7677(10) 0.034(6) Uiso 1.0 4 d . . . H9 H 0.9250 0.5099 0.7712 0.0240 Uiso 1.0 4 calc R . . H10 H 1.1374 0.5872 0.7132 0.0267 Uiso 1.0 4 calc R . . H11 H 1.2036 0.4884 0.6241 0.0267 Uiso 1.0 4 calc R . . H12 H 1.0684 0.3055 0.5923 0.0244 Uiso 1.0 4 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0345(2) 0.0255(2) 0.02381(18) -0.00896(16) 0.00179(14) -0.00691(14) Cl2 0.03105(19) 0.0265(2) 0.01755(16) 0.00074(15) 0.00352(13) -0.00683(13) F1 0.0241(5) 0.0169(5) 0.0230(4) 0.0036(4) 0.0069(4) 0.0003(4) F2 0.0378(5) 0.0265(5) 0.0175(4) 0.0080(4) 0.0121(4) 0.0045(4) F3 0.0195(5) 0.0287(6) 0.0404(6) -0.0027(4) 0.0098(4) -0.0104(5) N1 0.0201(6) 0.0166(6) 0.0149(6) -0.0005(5) 0.0025(5) -0.0002(5) N2 0.0183(6) 0.0152(6) 0.0140(5) 0.0002(5) 0.0041(4) -0.0008(5) N3 0.0190(6) 0.0163(6) 0.0167(6) 0.0003(5) 0.0034(5) -0.0017(5) C1 0.0211(7) 0.0182(7) 0.0167(6) -0.0009(6) 0.0011(5) 0.0010(6) C2 0.0243(7) 0.0162(7) 0.0186(7) -0.0010(6) -0.0018(6) -0.0010(6) C3 0.0248(7) 0.0181(7) 0.0146(6) 0.0040(6) 0.0014(5) -0.0012(5) C4 0.0220(7) 0.0184(7) 0.0154(6) 0.0019(6) 0.0031(5) 0.0002(5) C5 0.0197(7) 0.0149(7) 0.0149(6) 0.0008(5) 0.0012(5) 0.0002(5) C6 0.0205(7) 0.0163(7) 0.0143(6) 0.0017(6) 0.0016(5) 0.0019(5) C7 0.0182(6) 0.0160(7) 0.0137(6) 0.0017(5) 0.0039(5) 0.0019(5) C8 0.0183(7) 0.0155(7) 0.0143(6) 0.0024(5) 0.0029(5) 0.0015(5) C9 0.0170(6) 0.0163(7) 0.0139(6) -0.0018(5) 0.0026(5) -0.0019(5) C10 0.0186(7) 0.0175(7) 0.0185(7) 0.0017(6) 0.0013(5) 0.0005(6) C11 0.0248(7) 0.0223(8) 0.0156(7) -0.0035(6) 0.0017(6) 0.0022(6) C12 0.0217(7) 0.0244(8) 0.0169(7) -0.0039(6) 0.0060(6) -0.0051(6) C13 0.0200(7) 0.0195(8) 0.0243(7) 0.0020(6) 0.0031(6) -0.0041(6) C14 0.0226(7) 0.0175(7) 0.0173(7) -0.0003(6) 0.0016(5) 0.0009(5) C15 0.0192(7) 0.0157(7) 0.0139(6) 0.0028(6) 0.0016(5) 0.0008(5) C16 0.0175(7) 0.0175(7) 0.0149(6) 0.0005(5) 0.0024(5) 0.0014(5) C17 0.0181(7) 0.0172(7) 0.0151(6) 0.0002(6) 0.0042(5) 0.0007(5) C18 0.0213(7) 0.0178(7) 0.0190(7) 0.0003(6) 0.0064(5) 0.0000(6) C19 0.0181(7) 0.0171(7) 0.0170(6) 0.0008(6) 0.0008(5) 0.0001(5) C20 0.0177(7) 0.0176(7) 0.0166(6) 0.0020(6) -0.0000(5) 0.0017(5) C21 0.0214(7) 0.0190(7) 0.0194(7) 0.0018(6) -0.0018(5) -0.0021(6) C22 0.0214(7) 0.0190(7) 0.0262(7) -0.0029(6) -0.0037(6) 0.0002(6) C23 0.0182(7) 0.0245(8) 0.0241(7) -0.0023(6) 0.0013(6) 0.0039(6) C24 0.0195(7) 0.0225(8) 0.0191(7) -0.0009(6) 0.0031(6) 0.0000(6) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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 Cl1 C2 1.7344(16) yes . . Cl2 C3 1.7354(15) yes . . F1 C18 1.3439(18) yes . . F2 C18 1.3431(17) yes . . F3 C18 1.3339(17) yes . . N1 C6 1.3762(18) yes . . N1 C7 1.3299(18) yes . . N2 C5 1.4072(18) yes . . N2 C7 1.4181(18) yes . . N2 C17 1.3915(19) yes . . N3 C15 1.3686(19) yes . . N3 C20 1.3887(19) yes . . C1 C2 1.383(2) yes . . C1 C6 1.399(2) yes . . C2 C3 1.409(2) yes . . C3 C4 1.385(2) yes . . C4 C5 1.395(2) yes . . C5 C6 1.411(2) yes . . C7 C8 1.414(2) yes . . C8 C9 1.492(2) yes . . C8 C15 1.3767(19) yes . . C9 C10 1.394(2) yes . . C9 C14 1.399(2) yes . . C10 C11 1.393(2) yes . . C11 C12 1.386(3) yes . . C12 C13 1.392(2) yes . . C13 C14 1.389(2) yes . . C15 C16 1.456(2) yes . . C16 C17 1.369(2) yes . . C16 C19 1.464(2) yes . . C17 C18 1.505(2) yes . . C19 C20 1.414(2) yes . . C19 C24 1.405(2) yes . . C20 C21 1.391(2) yes . . C21 C22 1.388(2) yes . . C22 C23 1.401(3) yes . . C23 C24 1.382(3) yes . . N3 H8 0.85(2) no . . C1 H1 0.950 no . . C4 H2 0.950 no . . C10 H3 0.950 no . . C11 H4 0.950 no . . C12 H5 0.950 no . . C13 H6 0.950 no . . C14 H7 0.950 no . . C21 H9 0.950 no . . C22 H10 0.950 no . . C23 H11 0.950 no . . C24 H12 0.950 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 C6 N1 C7 105.11(12) yes . . . C5 N2 C7 105.54(11) yes . . . C5 N2 C17 132.60(12) yes . . . C7 N2 C17 121.85(12) yes . . . C15 N3 C20 109.36(12) yes . . . C2 C1 C6 117.96(13) yes . . . Cl1 C2 C1 118.81(12) yes . . . Cl1 C2 C3 120.05(11) yes . . . C1 C2 C3 121.12(14) yes . . . Cl2 C3 C2 120.87(11) yes . . . Cl2 C3 C4 117.49(11) yes . . . C2 C3 C4 121.64(13) yes . . . C3 C4 C5 117.21(13) yes . . . N2 C5 C4 133.59(13) yes . . . N2 C5 C6 104.81(12) yes . . . C4 C5 C6 121.53(13) yes . . . N1 C6 C1 127.62(13) yes . . . N1 C6 C5 111.92(12) yes . . . C1 C6 C5 120.45(13) yes . . . N1 C7 N2 112.54(12) yes . . . N1 C7 C8 127.41(13) yes . . . N2 C7 C8 120.02(12) yes . . . C7 C8 C9 120.99(12) yes . . . C7 C8 C15 116.71(13) yes . . . C9 C8 C15 122.30(13) yes . . . C8 C9 C10 120.16(13) yes . . . C8 C9 C14 120.63(12) yes . . . C10 C9 C14 119.19(13) yes . . . C9 C10 C11 120.40(14) yes . . . C10 C11 C12 120.11(14) yes . . . C11 C12 C13 119.84(13) yes . . . C12 C13 C14 120.26(14) yes . . . C9 C14 C13 120.19(13) yes . . . N3 C15 C8 128.15(13) yes . . . N3 C15 C16 108.52(12) yes . . . C8 C15 C16 123.15(13) yes . . . C15 C16 C17 118.45(13) yes . . . C15 C16 C19 105.96(12) yes . . . C17 C16 C19 135.56(13) yes . . . N2 C17 C16 118.92(13) yes . . . N2 C17 C18 117.39(12) yes . . . C16 C17 C18 123.32(13) yes . . . F1 C18 F2 107.22(11) yes . . . F1 C18 F3 105.91(11) yes . . . F1 C18 C17 111.20(12) yes . . . F2 C18 F3 107.17(12) yes . . . F2 C18 C17 112.85(12) yes . . . F3 C18 C17 112.11(12) yes . . . C16 C19 C20 105.78(12) yes . . . C16 C19 C24 135.13(13) yes . . . C20 C19 C24 118.63(14) yes . . . N3 C20 C19 110.18(13) yes . . . N3 C20 C21 127.22(13) yes . . . C19 C20 C21 122.56(13) yes . . . C20 C21 C22 117.26(13) yes . . . C21 C22 C23 121.25(14) yes . . . C22 C23 C24 121.23(14) yes . . . C19 C24 C23 118.95(14) yes . . . C15 N3 H8 126.4(14) no . . . C20 N3 H8 122.8(15) no . . . C2 C1 H1 121.016 no . . . C6 C1 H1 121.022 no . . . C3 C4 H2 121.392 no . . . C5 C4 H2 121.396 no . . . C9 C10 H3 119.797 no . . . C11 C10 H3 119.803 no . . . C10 C11 H4 119.940 no . . . C12 C11 H4 119.950 no . . . C11 C12 H5 120.075 no . . . C13 C12 H5 120.083 no . . . C12 C13 H6 119.868 no . . . C14 C13 H6 119.870 no . . . C9 C14 H7 119.912 no . . . C13 C14 H7 119.899 no . . . C20 C21 H9 121.368 no . . . C22 C21 H9 121.376 no . . . C21 C22 H10 119.380 no . . . C23 C22 H10 119.367 no . . . C22 C23 H11 119.390 no . . . C24 C23 H11 119.383 no . . . C19 C24 H12 120.523 no . . . C23 C24 H12 120.529 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 C6 N1 C7 N2 -2.01(14) no . . . . C6 N1 C7 C8 176.34(12) no . . . . C7 N1 C6 C1 -178.53(12) no . . . . C7 N1 C6 C5 0.39(15) no . . . . C5 N2 C7 N1 2.86(14) no . . . . C5 N2 C7 C8 -175.63(11) no . . . . C7 N2 C5 C4 174.45(13) no . . . . C7 N2 C5 C6 -2.38(13) no . . . . C5 N2 C17 C16 169.23(12) no . . . . C5 N2 C17 C18 -17.5(2) no . . . . C17 N2 C5 C4 -5.5(3) no . . . . C17 N2 C5 C6 177.65(13) no . . . . C7 N2 C17 C16 -10.73(18) no . . . . C7 N2 C17 C18 162.51(11) no . . . . C17 N2 C7 N1 -177.16(11) no . . . . C17 N2 C7 C8 4.35(18) no . . . . C15 N3 C20 C19 -2.73(15) no . . . . C15 N3 C20 C21 174.88(12) no . . . . C20 N3 C15 C8 179.44(12) no . . . . C20 N3 C15 C16 4.34(15) no . . . . C2 C1 C6 N1 178.04(12) no . . . . C2 C1 C6 C5 -0.8(2) no . . . . C6 C1 C2 Cl1 -179.30(11) no . . . . C6 C1 C2 C3 -1.0(2) no . . . . Cl1 C2 C3 Cl2 -0.45(18) no . . . . Cl1 C2 C3 C4 178.93(9) no . . . . C1 C2 C3 Cl2 -178.72(12) no . . . . C1 C2 C3 C4 0.7(2) no . . . . Cl2 C3 C4 C5 -179.12(9) no . . . . C2 C3 C4 C5 1.5(2) no . . . . C3 C4 C5 N2 -179.69(13) no . . . . C3 C4 C5 C6 -3.3(2) no . . . . N2 C5 C6 N1 1.33(15) no . . . . N2 C5 C6 C1 -179.67(11) no . . . . C4 C5 C6 N1 -175.98(12) no . . . . C4 C5 C6 C1 3.0(2) no . . . . N1 C7 C8 C9 4.9(2) no . . . . N1 C7 C8 C15 -174.92(12) no . . . . N2 C7 C8 C9 -176.85(11) no . . . . N2 C7 C8 C15 3.33(18) no . . . . C7 C8 C9 C10 77.46(16) no . . . . C7 C8 C9 C14 -103.83(15) no . . . . C7 C8 C15 N3 -179.21(12) no . . . . C7 C8 C15 C16 -4.76(19) no . . . . C9 C8 C15 N3 1.0(3) no . . . . C9 C8 C15 C16 175.42(11) no . . . . C15 C8 C9 C10 -102.73(15) no . . . . C15 C8 C9 C14 75.99(17) no . . . . C8 C9 C10 C11 178.20(11) no . . . . C8 C9 C14 C13 -178.35(11) no . . . . C10 C9 C14 C13 0.4(2) no . . . . C14 C9 C10 C11 -0.5(2) no . . . . C9 C10 C11 C12 0.2(2) no . . . . C10 C11 C12 C13 0.3(2) no . . . . C11 C12 C13 C14 -0.5(2) no . . . . C12 C13 C14 C9 0.1(2) no . . . . N3 C15 C16 C17 173.93(11) no . . . . N3 C15 C16 C19 -4.25(14) no . . . . C8 C15 C16 C17 -1.5(2) no . . . . C8 C15 C16 C19 -179.65(12) no . . . . C15 C16 C17 N2 9.10(19) no . . . . C15 C16 C17 C18 -163.71(11) no . . . . C15 C16 C19 C20 2.54(14) no . . . . C15 C16 C19 C24 -169.22(14) no . . . . C17 C16 C19 C20 -175.18(15) no . . . . C17 C16 C19 C24 13.1(3) no . . . . C19 C16 C17 N2 -173.39(14) no . . . . C19 C16 C17 C18 13.8(3) no . . . . N2 C17 C18 F1 -38.79(16) no . . . . N2 C17 C18 F2 81.74(15) no . . . . N2 C17 C18 F3 -157.14(11) no . . . . C16 C17 C18 F1 134.13(13) no . . . . C16 C17 C18 F2 -105.35(15) no . . . . C16 C17 C18 F3 15.78(19) no . . . . C16 C19 C20 N3 -0.01(15) no . . . . C16 C19 C20 C21 -177.76(11) no . . . . C16 C19 C24 C23 173.75(14) no . . . . C20 C19 C24 C23 2.8(2) no . . . . C24 C19 C20 N3 173.38(12) no . . . . C24 C19 C20 C21 -4.4(2) no . . . . N3 C20 C21 C22 -174.55(12) no . . . . C19 C20 C21 C22 2.8(2) no . . . . C20 C21 C22 C23 0.3(2) no . . . . C21 C22 C23 C24 -1.7(3) no . . . . C22 C23 C24 C19 0.1(3) no . . . . 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 Cl1 Cl2 3.1676(7) no . . F1 N2 2.7575(15) no . . F1 C4 2.8097(17) no . . F1 C5 2.9048(17) no . . F1 C16 3.5205(18) no . . F2 N2 3.1189(16) no . . F2 C4 3.0817(18) no . . F2 C5 3.3695(18) no . . F2 C16 3.3625(18) no . . F3 N2 3.5879(16) no . . F3 C16 2.7793(17) no . . F3 C19 2.9121(18) no . . F3 C24 2.7951(19) no . . N1 C9 3.0001(18) no . . N1 C10 3.5079(19) no . . N1 C17 3.5907(19) no . . N2 C1 3.5688(19) no . . N2 C15 2.7430(18) no . . N3 C9 3.0251(19) no . . N3 C14 3.499(2) no . . N3 C17 3.5644(19) no . . C1 C4 2.850(2) no . . C1 C7 3.516(2) no . . C2 C5 2.763(2) no . . C3 C6 2.767(2) no . . C4 C17 3.312(2) no . . C4 C18 3.203(2) no . . C5 C8 3.593(2) no . . C5 C18 3.072(2) no . . C6 C8 3.535(2) no . . C7 C10 3.289(2) no . . C7 C14 3.495(2) no . . C7 C16 2.811(2) no . . C8 C17 2.862(2) no . . C8 C20 3.592(2) no . . C9 C12 2.794(2) no . . C10 C13 2.778(2) no . . C10 C15 3.464(2) no . . C11 C14 2.782(2) no . . C14 C15 3.282(2) no . . C15 C21 3.598(2) no . . C17 C24 3.444(2) no . . C18 C19 3.260(2) no . . C18 C24 3.524(3) no . . C19 C22 2.788(3) no . . C20 C23 2.752(2) no . . C21 C24 2.838(2) no . . Cl1 F2 3.3884(12) no . 3_656 Cl2 N2 3.4533(13) no . 3_656 F1 F2 2.8224(14) no . 3_756 F1 C1 3.5992(17) no . 1_655 F1 C12 3.3072(19) no . 2_646 F1 C13 3.2470(18) no . 2_646 F2 Cl1 3.3884(12) no . 3_656 F2 F1 2.8224(14) no . 3_756 F2 F2 2.7819(14) no . 3_756 F2 F3 3.1810(14) no . 3_756 F2 C1 3.2345(17) no . 3_656 F2 C2 3.0481(18) no . 3_656 F2 C3 3.5289(19) no . 3_656 F2 C18 3.1495(18) no . 3_756 F3 F2 3.1810(14) no . 3_756 F3 N1 3.5677(15) no . 1_655 N1 F3 3.5677(15) no . 1_455 N1 N3 2.8852(17) no . 2_646 N1 C14 3.5200(19) no . 2_646 N2 Cl2 3.4533(13) no . 3_656 N2 C13 3.391(2) no . 2_646 N3 N1 2.8852(17) no . 2_656 N3 C10 3.295(2) no . 2_656 C1 F1 3.5992(17) no . 1_455 C1 F2 3.2345(17) no . 3_656 C1 C11 3.597(2) no . 2_646 C2 F2 3.0481(18) no . 3_656 C3 F2 3.5289(19) no . 3_656 C4 C4 3.407(2) no . 3_656 C4 C5 3.568(2) no . 3_656 C4 C12 3.472(2) no . 2_646 C5 C4 3.568(2) no . 3_656 C5 C12 3.346(2) no . 2_646 C5 C13 3.349(2) no . 2_646 C6 C12 3.579(2) no . 2_646 C6 C13 3.531(2) no . 2_646 C10 N3 3.295(2) no . 2_646 C10 C20 3.453(2) no . 2_646 C11 C1 3.597(2) no . 2_656 C11 C20 3.359(2) no . 2_646 C11 C21 3.500(2) no . 2_646 C12 F1 3.3072(19) no . 2_656 C12 C4 3.472(2) no . 2_656 C12 C5 3.346(2) no . 2_656 C12 C6 3.579(2) no . 2_656 C12 C21 3.415(2) no . 2_646 C12 C22 3.388(3) no . 2_646 C13 F1 3.2470(18) no . 2_656 C13 N2 3.391(2) no . 2_656 C13 C5 3.349(2) no . 2_656 C13 C6 3.531(2) no . 2_656 C13 C21 3.472(3) no . 2_646 C13 C22 3.527(3) no . 2_646 C14 N1 3.5200(19) no . 2_656 C15 C22 3.521(2) no . 2_746 C18 F2 3.1495(18) no . 3_756 C20 C10 3.453(2) no . 2_656 C20 C11 3.359(2) no . 2_656 C21 C11 3.500(2) no . 2_656 C21 C12 3.415(2) no . 2_656 C21 C13 3.472(3) no . 2_656 C22 C12 3.388(3) no . 2_656 C22 C13 3.527(3) no . 2_656 C22 C15 3.521(2) no . 2_756 Cl1 H1 2.7985 no . . Cl2 H2 2.7781 no . . F1 H2 2.3800 no . . F2 H2 2.3368 no . . F2 H12 3.2713 no . . F3 H12 2.2556 no . . N1 H1 2.7431 no . . N1 H3 3.4673 no . . N2 H2 2.8678 no . . N3 H7 3.4609 no . . N3 H9 2.7429 no . . C2 H2 3.3015 no . . C3 H1 3.2929 no . . C5 H1 3.3018 no . . C6 H2 3.3099 no . . C7 H3 3.2300 no . . C7 H7 3.5769 no . . C8 H3 2.6575 no . . C8 H7 2.6729 no . . C8 H8 2.76(2) no . . C9 H4 3.2748 no . . C9 H6 3.2735 no . . C9 H8 2.88(2) no . . C10 H5 3.2664 no . . C10 H7 3.2679 no . . C11 H6 3.2605 no . . C12 H3 3.2635 no . . C12 H7 3.2680 no . . C13 H4 3.2618 no . . C14 H3 3.2679 no . . C14 H5 3.2688 no . . C14 H8 3.12(2) no . . C15 H3 3.5473 no . . C15 H7 3.2413 no . . C16 H8 3.12(3) no . . C16 H12 2.9340 no . . C17 H2 3.1980 no . . C17 H12 3.3515 no . . C18 H2 2.7027 no . . C18 H12 3.0555 no . . C19 H8 3.10(2) no . . C19 H9 3.3186 no . . C19 H11 3.2592 no . . C20 H10 3.2351 no . . C20 H12 3.2888 no . . C21 H8 2.72(2) no . . C21 H11 3.2787 no . . C22 H12 3.2830 no . . C23 H9 3.2930 no . . C24 H10 3.2728 no . . H3 H4 2.3397 no . . H4 H5 2.3362 no . . H5 H6 2.3413 no . . H6 H7 2.3359 no . . H7 H8 3.1428 no . . H8 H9 2.6804 no . . H9 H10 2.3485 no . . H10 H11 2.3333 no . . H11 H12 2.3306 no . . Cl1 H4 3.0210 no . 4_544 Cl1 H11 3.0858 no . 1_445 Cl1 H12 3.4099 no . 3_656 Cl2 H3 3.5813 no . 4_544 Cl2 H4 3.0110 no . 4_544 Cl2 H11 3.2332 no . 3_756 Cl2 H12 3.1235 no . 3_756 F1 H1 3.1064 no . 1_655 F1 H5 2.7934 no . 2_646 F1 H6 2.6721 no . 2_646 F2 H1 3.4409 no . 3_656 F2 H2 3.5433 no . 3_756 F3 H2 3.0845 no . 3_756 F3 H9 3.1713 no . 2_746 N1 H8 2.05(3) no . 2_646 N1 H9 3.1311 no . 2_646 N2 H6 3.1311 no . 2_646 N3 H1 3.4507 no . 2_656 N3 H3 3.1717 no . 2_656 N3 H10 2.7381 no . 2_746 C1 H8 3.27(2) no . 2_646 C1 H11 3.4366 no . 1_445 C2 H4 3.5043 no . 2_646 C3 H5 3.4901 no . 2_646 C4 H2 3.5056 no . 3_656 C4 H5 3.1852 no . 2_646 C5 H2 3.4683 no . 3_656 C5 H5 3.3893 no . 2_646 C5 H6 3.3999 no . 2_646 C6 H8 2.87(2) no . 2_646 C7 H6 3.5619 no . 2_646 C7 H7 3.5940 no . 2_646 C7 H8 3.04(3) no . 2_646 C8 H10 3.0327 no . 2_746 C9 H8 3.40(3) no . 2_646 C9 H9 3.3886 no . 2_646 C9 H10 3.4971 no . 2_746 C10 H7 3.5293 no . 2_646 C10 H8 3.12(2) no . 2_646 C10 H10 3.3687 no . 2_746 C10 H11 3.1410 no . 2_746 C13 H9 3.3927 no . 2_646 C13 H10 3.4806 no . 2_646 C14 H3 3.4155 no . 2_656 C14 H9 3.2382 no . 2_646 C15 H3 3.5126 no . 2_656 C15 H10 2.6671 no . 2_746 C16 H9 3.3773 no . 2_746 C16 H10 3.1723 no . 2_746 C17 H6 3.3594 no . 2_646 C17 H9 3.5485 no . 2_746 C18 H6 3.4760 no . 2_646 C19 H4 3.5244 no . 2_656 C19 H7 3.5751 no . 1_655 C19 H9 3.5930 no . 2_746 C19 H10 3.5788 no . 2_746 C20 H4 3.5197 no . 2_656 C20 H6 3.2087 no . 1_655 C20 H10 3.3182 no . 2_746 C21 H6 2.9069 no . 1_655 C21 H7 3.4853 no . 1_655 C22 H1 3.5821 no . 1_665 C22 H3 3.1512 no . 2_756 C22 H5 3.4483 no . 2_656 C22 H6 3.4002 no . 1_655 C22 H7 3.1064 no . 1_655 C23 H1 3.4920 no . 1_665 C23 H3 2.9371 no . 2_756 C23 H5 3.5042 no . 2_656 C23 H7 2.9980 no . 1_655 C24 H7 3.2522 no . 1_655 H1 F1 3.1064 no . 1_455 H1 F2 3.4409 no . 3_656 H1 N3 3.4507 no . 2_646 H1 C22 3.5821 no . 1_445 H1 C23 3.4920 no . 1_445 H1 H5 3.5006 no . 2_546 H1 H8 2.9731 no . 2_646 H1 H10 3.1025 no . 1_445 H1 H11 2.9122 no . 1_445 H2 F2 3.5433 no . 3_756 H2 F3 3.0845 no . 3_756 H2 C4 3.5056 no . 3_656 H2 C5 3.4683 no . 3_656 H2 H5 3.3714 no . 2_646 H3 Cl2 3.5813 no . 4_545 H3 N3 3.1717 no . 2_646 H3 C14 3.4155 no . 2_646 H3 C15 3.5126 no . 2_646 H3 C22 3.1512 no . 2_746 H3 C23 2.9371 no . 2_746 H3 H7 2.6423 no . 2_646 H3 H8 2.9702 no . 2_646 H3 H10 2.8963 no . 2_746 H3 H11 2.5143 no . 2_746 H4 Cl1 3.0210 no . 4_545 H4 Cl2 3.0110 no . 4_545 H4 C2 3.5043 no . 2_656 H4 C19 3.5244 no . 2_646 H4 C20 3.5197 no . 2_646 H4 H11 3.4882 no . 2_746 H5 F1 2.7934 no . 2_656 H5 C3 3.4901 no . 2_656 H5 C4 3.1852 no . 2_656 H5 C5 3.3893 no . 2_656 H5 C22 3.4483 no . 2_646 H5 C23 3.5042 no . 2_646 H5 H1 3.5006 no . 2_556 H5 H2 3.3714 no . 2_656 H6 F1 2.6721 no . 2_656 H6 N2 3.1311 no . 2_656 H6 C5 3.3999 no . 2_656 H6 C7 3.5619 no . 2_656 H6 C17 3.3594 no . 2_656 H6 C18 3.4760 no . 2_656 H6 C20 3.2087 no . 1_455 H6 C21 2.9069 no . 1_455 H6 C22 3.4002 no . 1_455 H6 H9 2.9379 no . 1_455 H6 H10 3.3863 no . 2_646 H7 C7 3.5940 no . 2_656 H7 C10 3.5293 no . 2_656 H7 C19 3.5751 no . 1_455 H7 C21 3.4853 no . 1_455 H7 C22 3.1064 no . 1_455 H7 C23 2.9980 no . 1_455 H7 C24 3.2522 no . 1_455 H7 H3 2.6423 no . 2_656 H7 H9 3.5584 no . 2_646 H7 H10 3.4596 no . 1_455 H7 H11 3.3187 no . 1_455 H8 N1 2.05(3) no . 2_656 H8 C1 3.27(2) no . 2_656 H8 C6 2.87(2) no . 2_656 H8 C7 3.04(3) no . 2_656 H8 C9 3.40(3) no . 2_656 H8 C10 3.12(2) no . 2_656 H8 H1 2.9731 no . 2_656 H8 H3 2.9702 no . 2_656 H8 H10 3.0790 no . 2_746 H9 F3 3.1713 no . 2_756 H9 N1 3.1311 no . 2_656 H9 C9 3.3886 no . 2_656 H9 C13 3.3927 no . 2_656 H9 C14 3.2382 no . 2_656 H9 C16 3.3773 no . 2_756 H9 C17 3.5485 no . 2_756 H9 C19 3.5930 no . 2_756 H9 H6 2.9379 no . 1_655 H9 H7 3.5584 no . 2_656 H10 N3 2.7381 no . 2_756 H10 C8 3.0327 no . 2_756 H10 C9 3.4971 no . 2_756 H10 C10 3.3687 no . 2_756 H10 C13 3.4806 no . 2_656 H10 C15 2.6671 no . 2_756 H10 C16 3.1723 no . 2_756 H10 C19 3.5788 no . 2_756 H10 C20 3.3182 no . 2_756 H10 H1 3.1025 no . 1_665 H10 H3 2.8963 no . 2_756 H10 H6 3.3863 no . 2_656 H10 H7 3.4596 no . 1_655 H10 H8 3.0790 no . 2_756 H11 Cl1 3.0858 no . 1_665 H11 Cl2 3.2332 no . 3_756 H11 C1 3.4366 no . 1_665 H11 C10 3.1410 no . 2_756 H11 H1 2.9122 no . 1_665 H11 H3 2.5143 no . 2_756 H11 H4 3.4882 no . 2_756 H11 H7 3.3187 no . 1_655 H12 Cl1 3.4099 no . 3_656 H12 Cl2 3.1235 no . 3_756 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N3 H8 N1 . . 2_656 2.8852(17) 0.85(2) 2.05(2) 167(2) 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 940146'