data_a008_0m _audit_creation_date 2014-03-17 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796) ; _shelxl_version_number 2013-4 _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790; Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984; Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45, 575-580 SHELXL-97 (Sheldrick, 2008) SHELXS-97 (Sheldrick, 2008) Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122 ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H12 Cl2 F3 N O5' _chemical_formula_sum 'C14 H12 Cl2 F3 N O5' _chemical_formula_weight 402.15 _chemical_absolute_configuration ? _chemical_melting_point ? 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' 'Cl' 'Cl' 0.1484 0.1585 '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' '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' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system 'triclinic' _space_group_IT_number 1 _space_group_name_H-M_alt 'P 1' _space_group_name_Hall 'P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' _cell_length_a 4.8784(8) _cell_length_b 10.6424(17) _cell_length_c 15.881(3) _cell_angle_alpha 99.955(2) _cell_angle_beta 96.953(2) _cell_angle_gamma 90.633(2) _cell_volume 805.7(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9984 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 31.003 _cell_measurement_theta_min 2.529 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.462 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_correction_T_min 0.6261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1261 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8391. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 408 _exptl_crystal_recrystallization_method 'The material was recrystallised from DCM by slow evaporation' _exptl_crystal_size_max 0.985 _exptl_crystal_size_mid 0.291 _exptl_crystal_size_min 0.135 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_unetI/netI 0.0616 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 14822 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.011 _diffrn_reflns_theta_min 1.944 _diffrn_ambient_temperature 110(2) _diffrn_detector_area_resol_mean 512 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_Friedel_coverage 1.000 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.993 _reflns_number_gt 8620 _reflns_number_total 9669 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection 'APEX2 v2013.6-2 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.724 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.079 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.53(6) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 452 _refine_ls_number_reflns 9669 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0495 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.0680P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1187 _refine_ls_wR_factor_ref 0.1238 _refine_special_details ; Refined as a 2-component inversion twin. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2.a Riding coordinates: N1'(H1'), N1(H1) 2.b Ternary CH refined with riding coordinates: C8'(H8'), C11'(H11'), C11(H11), C8(H8) 2.c Secondary CH2 refined with riding coordinates: C10'(H10A,H10B), C13'(H13A,H13B), C9'(H9'A,H9'B), C10(H10C,H10D), C13(H13C, H13D), C9(H9A,H9B) 2.d Aromatic/amide H refined with riding coordinates: C5'(H5'), C2'(H2'), C4'(H4'), C2(H2), C5(H5), C4(H4) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl2' Cl -0.14978(19) 0.71828(10) -0.13176(6) 0.0319(2) Uani 1 1 d . . . . . Cl1' Cl 0.65352(19) 1.00326(8) 0.07297(6) 0.02722(19) Uani 1 1 d . . . . . F2' F 0.6201(5) 0.1660(3) -0.08936(17) 0.0396(6) Uani 1 1 d . . . . . F3' F 0.9845(7) 0.1847(4) -0.15049(19) 0.0554(9) Uani 1 1 d . . . . . F1' F 0.7888(7) 0.3511(3) -0.0930(2) 0.0561(9) Uani 1 1 d . . . . . O5' O 0.9950(6) 0.8320(2) 0.16566(18) 0.0238(5) Uani 1 1 d . . . . . O3' O 0.8854(5) 0.2818(2) 0.06745(18) 0.0248(5) Uani 1 1 d . . . . . O1' O 0.7852(5) 0.6552(2) 0.19118(16) 0.0189(5) Uani 1 1 d . . . . . O2' O 1.0259(6) 0.7138(3) 0.32956(18) 0.0258(5) Uani 1 1 d . . . . . O4' O 1.2781(5) 0.3823(3) 0.14154(18) 0.0240(5) Uani 1 1 d . . . . . N1' N 0.8615(6) 0.4059(3) 0.19320(19) 0.0175(5) Uani 1 1 d . . . . . H1' H 0.6862 0.3810 0.1851 0.021 Uiso 1 1 d R . . . . C10' C 0.7666(7) 0.5239(4) 0.3354(2) 0.0205(6) Uani 1 1 d . . . . . H10A H 0.7751 0.4596 0.3721 0.025 Uiso 1 1 calc R . . . . H10B H 0.5785 0.5272 0.3080 0.025 Uiso 1 1 calc R . . . . C5' C 0.4193(7) 0.6343(3) 0.0500(2) 0.0216(7) Uani 1 1 d . . . . . H5' H 0.4686 0.5633 0.0747 0.026 Uiso 1 1 calc R . . . . C14' C 0.8568(9) 0.2330(4) -0.0835(3) 0.0300(8) Uani 1 1 d . . . . . C1' C 0.4909(7) 0.8547(3) 0.0412(2) 0.0192(6) Uani 1 1 d . . . . . C12' C 1.0283(7) 0.3595(3) 0.1361(2) 0.0179(6) Uani 1 1 d . . . . . C8' C 1.0189(7) 0.6325(3) 0.2508(2) 0.0194(6) Uani 1 1 d . . . . . H8' H 1.1925 0.6387 0.2262 0.023 Uiso 1 1 calc R . . . . C2' C 0.2696(8) 0.8452(4) -0.0241(2) 0.0227(7) Uani 1 1 d . . . . . H2' H 0.2187 0.9157 -0.0491 0.027 Uiso 1 1 calc R . . . . C7' C 0.8068(7) 0.7547(3) 0.1489(2) 0.0173(6) Uani 1 1 d . . . . . C13' C 1.0392(8) 0.2319(4) -0.0010(3) 0.0263(7) Uani 1 1 d . . . . . H13A H 1.0928 0.1455 0.0034 0.032 Uiso 1 1 calc R . . . . H13B H 1.2051 0.2842 0.0016 0.032 Uiso 1 1 calc R . . . . C6' C 0.5685(7) 0.7497(3) 0.0795(2) 0.0173(6) Uani 1 1 d . . . . . C9' C 0.8712(8) 0.6544(4) 0.3861(3) 0.0269(8) Uani 1 1 d . . . . . H9'A H 0.7173 0.7063 0.4023 0.032 Uiso 1 1 calc R . . . . H9'B H 0.9895 0.6447 0.4381 0.032 Uiso 1 1 calc R . . . . C11' C 0.9682(7) 0.4979(3) 0.2690(2) 0.0182(6) Uani 1 1 d . . . . . H11' H 1.1406 0.4674 0.2958 0.022 Uiso 1 1 calc R . . . . C3' C 0.1271(8) 0.7295(4) -0.0513(2) 0.0233(7) Uani 1 1 d . . . . . C4' C 0.1994(8) 0.6233(4) -0.0153(2) 0.0234(7) Uani 1 1 d . . . . . H4' H 0.1024 0.5459 -0.0346 0.028 Uiso 1 1 calc R . . . . Cl2 Cl 1.3291(2) 0.45615(11) 0.77484(7) 0.0359(2) Uani 1 1 d . . . . . Cl1 Cl 0.5545(2) 0.62881(8) 0.56142(6) 0.0286(2) Uani 1 1 d . . . . . F1 F 0.4230(7) 0.0686(3) 0.7179(2) 0.0484(7) Uani 1 1 d . . . . . F2 F 0.6006(6) -0.1139(3) 0.71936(18) 0.0390(6) Uani 1 1 d . . . . . F3 F 0.2370(6) -0.0681(4) 0.78075(19) 0.0514(8) Uani 1 1 d . . . . . O5 O 0.2038(6) 0.4068(2) 0.47151(18) 0.0249(5) Uani 1 1 d . . . . . O1 O 0.4218(5) 0.2215(2) 0.44279(17) 0.0198(5) Uani 1 1 d . . . . . O4 O -0.0642(5) -0.0283(3) 0.49010(18) 0.0252(5) Uani 1 1 d . . . . . O3 O 0.3255(5) -0.0941(3) 0.56129(18) 0.0246(5) Uani 1 1 d . . . . . O2 O 0.1831(6) 0.2103(3) 0.30420(17) 0.0256(5) Uani 1 1 d . . . . . N1 N 0.3484(6) -0.0306(3) 0.43648(19) 0.0182(5) Uani 1 1 d . . . . . H1 H 0.5225 -0.0517 0.4436 0.022 Uiso 1 1 d R . . . . C11 C 0.2417(7) 0.0232(3) 0.3619(2) 0.0166(6) Uani 1 1 d . . . . . H11 H 0.0701 -0.0229 0.3346 0.020 Uiso 1 1 calc R . . . . C1 C 0.7087(7) 0.4978(3) 0.5958(2) 0.0189(6) Uani 1 1 d . . . . . C2 C 0.9257(8) 0.5239(4) 0.6626(2) 0.0246(7) Uani 1 1 d . . . . . H2 H 0.9798 0.6077 0.6869 0.029 Uiso 1 1 calc R . . . . C12 C 0.1817(7) -0.0483(3) 0.4944(2) 0.0177(6) Uani 1 1 d . . . . . C6 C 0.6267(7) 0.3724(3) 0.5584(2) 0.0187(6) Uani 1 1 d . . . . . C3 C 1.0589(8) 0.4230(4) 0.6920(2) 0.0244(7) Uani 1 1 d . . . . . C8 C 0.1880(7) 0.1666(3) 0.3817(2) 0.0184(6) Uani 1 1 d . . . . . H8 H 0.0136 0.1822 0.4060 0.022 Uiso 1 1 calc R . . . . C7 C 0.3924(7) 0.3405(3) 0.4874(2) 0.0166(6) Uani 1 1 d . . . . . C10 C 0.4433(7) 0.0201(3) 0.2955(2) 0.0204(6) Uani 1 1 d . . . . . H10C H 0.4342 -0.0621 0.2575 0.024 Uiso 1 1 calc R . . . . H10D H 0.6314 0.0383 0.3230 0.024 Uiso 1 1 calc R . . . . C14 C 0.3597(9) -0.0550(4) 0.7125(3) 0.0296(8) Uani 1 1 d . . . . . C5 C 0.7686(8) 0.2731(3) 0.5901(2) 0.0230(7) Uani 1 1 d . . . . . H5 H 0.7176 0.1889 0.5660 0.028 Uiso 1 1 calc R . . . . C4 C 0.9829(8) 0.2981(4) 0.6567(3) 0.0265(7) Uani 1 1 d . . . . . H4 H 1.0747 0.2314 0.6774 0.032 Uiso 1 1 calc R . . . . C13 C 0.1757(8) -0.1069(4) 0.6312(3) 0.0266(8) Uani 1 1 d . . . . . H13C H 0.1269 -0.1959 0.6297 0.032 Uiso 1 1 calc R . . . . H13D H 0.0073 -0.0594 0.6277 0.032 Uiso 1 1 calc R . . . . C9 C 0.3406(8) 0.1256(4) 0.2468(2) 0.0251(7) Uani 1 1 d . . . . . H9A H 0.4953 0.1720 0.2323 0.030 Uiso 1 1 calc R . . . . H9B H 0.2241 0.0897 0.1940 0.030 Uiso 1 1 calc R . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2' 0.0246(4) 0.0480(6) 0.0214(4) 0.0052(4) -0.0030(3) 0.0083(4) Cl1' 0.0347(5) 0.0161(3) 0.0321(5) 0.0072(3) 0.0047(4) -0.0004(3) F2' 0.0292(13) 0.0526(16) 0.0335(14) 0.0016(12) -0.0003(10) -0.0179(12) F3' 0.0407(17) 0.092(3) 0.0292(14) -0.0031(15) 0.0092(12) -0.0096(17) F1' 0.059(2) 0.0428(17) 0.067(2) 0.0261(15) -0.0133(17) -0.0016(15) O5' 0.0245(13) 0.0203(12) 0.0269(13) 0.0056(10) 0.0023(10) -0.0044(10) O3' 0.0148(11) 0.0257(13) 0.0311(14) -0.0028(11) 0.0030(10) -0.0024(9) O1' 0.0143(11) 0.0195(11) 0.0232(12) 0.0079(9) -0.0019(9) -0.0017(9) O2' 0.0290(14) 0.0232(12) 0.0236(13) 0.0019(10) 0.0002(11) -0.0057(10) O4' 0.0111(11) 0.0274(13) 0.0331(14) 0.0064(11) 0.0002(10) -0.0018(9) N1' 0.0098(12) 0.0166(12) 0.0247(15) 0.0024(10) -0.0016(10) -0.0016(9) C10' 0.0163(15) 0.0244(16) 0.0216(16) 0.0069(13) 0.0009(12) 0.0005(12) C5' 0.0218(17) 0.0205(15) 0.0228(17) 0.0060(13) 0.0007(13) 0.0006(12) C14' 0.0259(19) 0.0315(19) 0.032(2) 0.0045(16) 0.0019(16) -0.0068(15) C1' 0.0202(16) 0.0154(14) 0.0229(17) 0.0044(12) 0.0057(13) 0.0012(12) C12' 0.0134(14) 0.0154(14) 0.0253(17) 0.0069(12) -0.0013(12) -0.0007(11) C8' 0.0153(14) 0.0191(15) 0.0234(17) 0.0063(12) -0.0021(12) -0.0029(11) C2' 0.0263(17) 0.0251(17) 0.0196(16) 0.0097(13) 0.0050(13) 0.0084(14) C7' 0.0159(14) 0.0170(14) 0.0190(15) 0.0033(12) 0.0025(12) 0.0018(11) C13' 0.0211(17) 0.0277(18) 0.0288(19) -0.0004(14) 0.0053(14) 0.0037(14) C6' 0.0191(15) 0.0176(14) 0.0164(15) 0.0050(11) 0.0039(12) 0.0013(12) C9' 0.0296(19) 0.0292(18) 0.0222(18) 0.0049(14) 0.0035(15) -0.0015(15) C11' 0.0127(14) 0.0180(14) 0.0234(17) 0.0065(12) -0.0035(11) -0.0026(11) C3' 0.0196(16) 0.0345(19) 0.0162(16) 0.0059(14) 0.0014(13) 0.0069(14) C4' 0.0235(17) 0.0227(16) 0.0225(18) 0.0027(13) -0.0018(14) -0.0020(13) Cl2 0.0249(5) 0.0524(6) 0.0257(5) -0.0008(4) -0.0041(4) -0.0063(4) Cl1 0.0383(5) 0.0158(3) 0.0316(5) 0.0038(3) 0.0044(4) 0.0016(3) F1 0.0596(19) 0.0315(14) 0.0502(17) 0.0007(12) 0.0003(15) -0.0014(13) F2 0.0287(12) 0.0546(16) 0.0354(13) 0.0146(12) -0.0002(10) 0.0144(11) F3 0.0426(16) 0.087(2) 0.0298(14) 0.0186(15) 0.0120(13) 0.0077(16) O5 0.0245(13) 0.0192(11) 0.0303(14) 0.0039(10) 0.0002(11) 0.0066(10) O1 0.0138(11) 0.0180(11) 0.0256(13) 0.0010(9) -0.0017(9) 0.0012(9) O4 0.0127(11) 0.0331(14) 0.0303(14) 0.0078(11) 0.0011(10) 0.0022(10) O3 0.0168(12) 0.0322(13) 0.0272(14) 0.0118(11) 0.0026(10) 0.0040(10) O2 0.0307(14) 0.0239(12) 0.0226(13) 0.0070(10) 0.0007(11) 0.0072(10) N1 0.0125(12) 0.0180(13) 0.0235(14) 0.0048(10) -0.0013(10) 0.0019(10) C11 0.0138(13) 0.0161(14) 0.0185(15) 0.0019(11) -0.0026(11) 0.0019(11) C1 0.0215(16) 0.0151(14) 0.0212(16) 0.0038(12) 0.0062(13) 0.0005(12) C2 0.0264(18) 0.0242(17) 0.0218(17) -0.0013(14) 0.0061(14) -0.0063(14) C12 0.0124(14) 0.0142(13) 0.0248(16) 0.0022(12) -0.0017(12) 0.0004(11) C6 0.0179(15) 0.0182(14) 0.0194(16) 0.0013(12) 0.0035(12) 0.0004(12) C3 0.0195(16) 0.0333(19) 0.0182(17) -0.0001(14) 0.0009(13) -0.0053(14) C8 0.0159(15) 0.0166(14) 0.0212(16) 0.0021(12) -0.0016(12) 0.0018(11) C7 0.0176(14) 0.0148(13) 0.0178(15) 0.0044(11) 0.0018(12) -0.0010(11) C10 0.0153(14) 0.0231(16) 0.0218(16) 0.0034(13) -0.0005(12) -0.0003(12) C14 0.0272(19) 0.033(2) 0.031(2) 0.0101(16) 0.0043(16) 0.0058(15) C5 0.0247(18) 0.0193(15) 0.0232(17) 0.0022(13) -0.0017(13) 0.0011(13) C4 0.0249(18) 0.0268(18) 0.0270(19) 0.0048(14) -0.0009(14) 0.0022(14) C13 0.0198(17) 0.0341(19) 0.0289(19) 0.0129(15) 0.0045(14) 0.0000(14) C9 0.0295(19) 0.0242(17) 0.0218(17) 0.0051(14) 0.0020(14) 0.0018(14) _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 Cl2' C3' 1.731(4) . ? Cl1' C1' 1.727(3) . ? F2' C14' 1.335(5) . ? F3' C14' 1.328(5) . ? F1' C14' 1.333(5) . ? O5' C7' 1.200(4) . ? O3' C12' 1.361(4) . ? O3' C13' 1.426(4) . ? O1' C8' 1.442(4) . ? O1' C7' 1.357(4) . ? O2' C8' 1.389(5) . ? O2' C9' 1.459(5) . ? O4' C12' 1.230(4) . ? N1' H1' 0.8800 . ? N1' C12' 1.327(4) . ? N1' C11' 1.452(4) . ? C10' H10A 0.9700 . ? C10' H10B 0.9700 . ? C10' C9' 1.529(5) . ? C10' C11' 1.520(5) . ? C5' H5' 0.9300 . ? C5' C6' 1.399(5) . ? C5' C4' 1.388(5) . ? C14' C13' 1.494(6) . ? C1' C2' 1.394(5) . ? C1' C6' 1.396(5) . ? C8' H8' 0.9800 . ? C8' C11' 1.533(5) . ? C2' H2' 0.9300 . ? C2' C3' 1.382(6) . ? C7' C6' 1.496(5) . ? C13' H13A 0.9700 . ? C13' H13B 0.9700 . ? C9' H9'A 0.9700 . ? C9' H9'B 0.9700 . ? C11' H11' 0.9800 . ? C3' C4' 1.383(5) . ? C4' H4' 0.9300 . ? Cl2 C3 1.733(4) . ? Cl1 C1 1.730(3) . ? F1 C14 1.334(5) . ? F2 C14 1.340(5) . ? F3 C14 1.326(5) . ? O5 C7 1.195(4) . ? O1 C8 1.451(4) . ? O1 C7 1.358(4) . ? O4 C12 1.216(4) . ? O3 C12 1.366(4) . ? O3 C13 1.426(4) . ? O2 C8 1.387(4) . ? O2 C9 1.461(5) . ? N1 H1 0.8799 . ? N1 C11 1.447(4) . ? N1 C12 1.334(4) . ? C11 H11 0.9800 . ? C11 C8 1.536(4) . ? C11 C10 1.523(5) . ? C1 C2 1.394(5) . ? C1 C6 1.397(5) . ? C2 H2 0.9300 . ? C2 C3 1.382(6) . ? C6 C7 1.497(5) . ? C6 C5 1.402(5) . ? C3 C4 1.378(6) . ? C8 H8 0.9800 . ? C10 H10C 0.9700 . ? C10 H10D 0.9700 . ? C10 C9 1.526(5) . ? C14 C13 1.497(6) . ? C5 H5 0.9300 . ? C5 C4 1.382(5) . ? C4 H4 0.9300 . ? C13 H13C 0.9700 . ? C13 H13D 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? 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 C12' O3' C13' 116.2(3) . . ? C7' O1' C8' 117.5(3) . . ? C8' O2' C9' 109.4(3) . . ? C12' N1' H1' 120.0 . . ? C12' N1' C11' 120.0(3) . . ? C11' N1' H1' 120.0 . . ? H10A C10' H10B 109.2 . . ? C9' C10' H10A 111.4 . . ? C9' C10' H10B 111.4 . . ? C11' C10' H10A 111.4 . . ? C11' C10' H10B 111.4 . . ? C11' C10' C9' 102.0(3) . . ? C6' C5' H5' 119.3 . . ? C4' C5' H5' 119.3 . . ? C4' C5' C6' 121.5(3) . . ? F2' C14' C13' 113.0(4) . . ? F3' C14' F2' 107.6(3) . . ? F3' C14' F1' 107.0(4) . . ? F3' C14' C13' 110.6(4) . . ? F1' C14' F2' 106.6(4) . . ? F1' C14' C13' 111.7(4) . . ? C2' C1' Cl1' 116.2(3) . . ? C2' C1' C6' 121.0(3) . . ? C6' C1' Cl1' 122.8(3) . . ? O4' C12' O3' 122.8(3) . . ? O4' C12' N1' 126.4(3) . . ? N1' C12' O3' 110.8(3) . . ? O1' C8' H8' 111.2 . . ? O1' C8' C11' 105.5(3) . . ? O2' C8' O1' 111.6(3) . . ? O2' C8' H8' 111.2 . . ? O2' C8' C11' 105.8(3) . . ? C11' C8' H8' 111.2 . . ? C1' C2' H2' 120.5 . . ? C3' C2' C1' 119.1(3) . . ? C3' C2' H2' 120.5 . . ? O5' C7' O1' 123.4(3) . . ? O5' C7' C6' 126.7(3) . . ? O1' C7' C6' 109.9(3) . . ? O3' C13' C14' 107.2(3) . . ? O3' C13' H13A 110.3 . . ? O3' C13' H13B 110.3 . . ? C14' C13' H13A 110.3 . . ? C14' C13' H13B 110.3 . . ? H13A C13' H13B 108.5 . . ? C5' C6' C7' 118.9(3) . . ? C1' C6' C5' 118.2(3) . . ? C1' C6' C7' 123.0(3) . . ? O2' C9' C10' 106.5(3) . . ? O2' C9' H9'A 110.4 . . ? O2' C9' H9'B 110.4 . . ? C10' C9' H9'A 110.4 . . ? C10' C9' H9'B 110.4 . . ? H9'A C9' H9'B 108.6 . . ? N1' C11' C10' 113.4(3) . . ? N1' C11' C8' 114.0(3) . . ? N1' C11' H11' 109.3 . . ? C10' C11' C8' 101.2(3) . . ? C10' C11' H11' 109.3 . . ? C8' C11' H11' 109.3 . . ? C2' C3' Cl2' 119.0(3) . . ? C2' C3' C4' 121.6(3) . . ? C4' C3' Cl2' 119.4(3) . . ? C5' C4' H4' 120.6 . . ? C3' C4' C5' 118.8(3) . . ? C3' C4' H4' 120.6 . . ? C7 O1 C8 116.6(3) . . ? C12 O3 C13 115.9(3) . . ? C8 O2 C9 109.4(3) . . ? C11 N1 H1 120.1 . . ? C12 N1 H1 120.2 . . ? C12 N1 C11 119.7(3) . . ? N1 C11 H11 109.2 . . ? N1 C11 C8 114.3(3) . . ? N1 C11 C10 113.6(3) . . ? C8 C11 H11 109.2 . . ? C10 C11 H11 109.2 . . ? C10 C11 C8 101.1(3) . . ? C2 C1 Cl1 116.2(3) . . ? C2 C1 C6 121.1(3) . . ? C6 C1 Cl1 122.7(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 C1 118.7(3) . . ? C3 C2 H2 120.6 . . ? O4 C12 O3 123.2(3) . . ? O4 C12 N1 126.4(3) . . ? N1 C12 O3 110.3(3) . . ? C1 C6 C7 122.7(3) . . ? C1 C6 C5 118.1(3) . . ? C5 C6 C7 119.2(3) . . ? C2 C3 Cl2 118.5(3) . . ? C4 C3 Cl2 119.9(3) . . ? C4 C3 C2 121.6(4) . . ? O1 C8 C11 105.1(3) . . ? O1 C8 H8 111.3 . . ? O2 C8 O1 111.5(3) . . ? O2 C8 C11 106.2(3) . . ? O2 C8 H8 111.3 . . ? C11 C8 H8 111.3 . . ? O5 C7 O1 123.9(3) . . ? O5 C7 C6 126.5(3) . . ? O1 C7 C6 109.6(3) . . ? C11 C10 H10C 111.3 . . ? C11 C10 H10D 111.3 . . ? C11 C10 C9 102.4(3) . . ? H10C C10 H10D 109.2 . . ? C9 C10 H10C 111.3 . . ? C9 C10 H10D 111.3 . . ? F1 C14 F2 106.2(4) . . ? F1 C14 C13 111.7(3) . . ? F2 C14 C13 112.9(3) . . ? F3 C14 F1 108.0(4) . . ? F3 C14 F2 107.3(3) . . ? F3 C14 C13 110.4(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C3 C4 C5 119.2(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? O3 C13 C14 107.1(3) . . ? O3 C13 H13C 110.3 . . ? O3 C13 H13D 110.3 . . ? C14 C13 H13C 110.3 . . ? C14 C13 H13D 110.3 . . ? H13C C13 H13D 108.6 . . ? O2 C9 C10 106.6(3) . . ? O2 C9 H9A 110.4 . . ? O2 C9 H9B 110.4 . . ? C10 C9 H9A 110.4 . . ? C10 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? 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 Cl2' C3' C4' C5' -179.1(3) . . . . ? Cl1' C1' C2' C3' -178.7(3) . . . . ? Cl1' C1' C6' C5' 178.8(3) . . . . ? Cl1' C1' C6' C7' -2.6(5) . . . . ? F2' C14' C13' O3' -57.8(4) . . . . ? F3' C14' C13' O3' -178.5(3) . . . . ? F1' C14' C13' O3' 62.5(4) . . . . ? O5' C7' C6' C5' 159.2(3) . . . . ? O5' C7' C6' C1' -19.4(5) . . . . ? O1' C8' C11' N1' 41.7(4) . . . . ? O1' C8' C11' C10' -80.4(3) . . . . ? O1' C7' C6' C5' -19.5(4) . . . . ? O1' C7' C6' C1' 161.9(3) . . . . ? O2' C8' C11' N1' 160.0(3) . . . . ? O2' C8' C11' C10' 37.9(3) . . . . ? C1' C2' C3' Cl2' 179.4(3) . . . . ? C1' C2' C3' C4' -0.2(5) . . . . ? C12' O3' C13' C14' -141.0(3) . . . . ? C12' N1' C11' C10' -169.8(3) . . . . ? C12' N1' C11' C8' 75.1(4) . . . . ? C8' O1' C7' O5' -8.7(5) . . . . ? C8' O1' C7' C6' 170.1(3) . . . . ? C8' O2' C9' C10' 0.9(4) . . . . ? C2' C1' C6' C5' 0.4(5) . . . . ? C2' C1' C6' C7' 179.1(3) . . . . ? C2' C3' C4' C5' 0.5(5) . . . . ? C7' O1' C8' O2' 80.5(3) . . . . ? C7' O1' C8' C11' -165.1(3) . . . . ? C13' O3' C12' O4' -2.9(5) . . . . ? C13' O3' C12' N1' 176.3(3) . . . . ? C6' C5' C4' C3' -0.3(5) . . . . ? C6' C1' C2' C3' -0.3(5) . . . . ? C9' O2' C8' O1' 89.9(3) . . . . ? C9' O2' C8' C11' -24.4(4) . . . . ? C9' C10' C11' N1' -158.0(3) . . . . ? C9' C10' C11' C8' -35.6(3) . . . . ? C11' N1' C12' O3' -176.0(3) . . . . ? C11' N1' C12' O4' 3.2(5) . . . . ? C11' C10' C9' O2' 22.8(4) . . . . ? C4' C5' C6' C1' -0.1(5) . . . . ? C4' C5' C6' C7' -178.9(3) . . . . ? Cl2 C3 C4 C5 -179.4(3) . . . . ? Cl1 C1 C2 C3 -179.2(3) . . . . ? Cl1 C1 C6 C7 -2.0(5) . . . . ? Cl1 C1 C6 C5 178.9(3) . . . . ? F1 C14 C13 O3 62.1(4) . . . . ? F2 C14 C13 O3 -57.6(4) . . . . ? F3 C14 C13 O3 -177.7(3) . . . . ? N1 C11 C8 O1 41.4(4) . . . . ? N1 C11 C8 O2 159.5(3) . . . . ? N1 C11 C10 C9 -157.5(3) . . . . ? C11 N1 C12 O4 3.3(5) . . . . ? C11 N1 C12 O3 -177.1(3) . . . . ? C11 C10 C9 O2 22.1(4) . . . . ? C1 C2 C3 Cl2 179.8(3) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C1 C6 C7 O5 -23.5(5) . . . . ? C1 C6 C7 O1 157.4(3) . . . . ? C1 C6 C5 C4 0.2(5) . . . . ? C2 C1 C6 C7 179.2(3) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? C12 O3 C13 C14 -135.5(3) . . . . ? C12 N1 C11 C8 73.0(4) . . . . ? C12 N1 C11 C10 -171.7(3) . . . . ? C6 C1 C2 C3 -0.4(5) . . . . ? C6 C5 C4 C3 -0.4(6) . . . . ? C8 O1 C7 O5 -9.8(5) . . . . ? C8 O1 C7 C6 169.3(3) . . . . ? C8 O2 C9 C10 1.2(4) . . . . ? C8 C11 C10 C9 -34.6(3) . . . . ? C7 O1 C8 O2 81.8(3) . . . . ? C7 O1 C8 C11 -163.7(3) . . . . ? C7 C6 C5 C4 -178.8(3) . . . . ? C10 C11 C8 O1 -81.1(3) . . . . ? C10 C11 C8 O2 37.1(3) . . . . ? C5 C6 C7 O5 155.5(4) . . . . ? C5 C6 C7 O1 -23.6(4) . . . . ? C13 O3 C12 O4 -5.5(5) . . . . ? C13 O3 C12 N1 174.9(3) . . . . ? C9 O2 C8 O1 89.7(3) . . . . ? C9 O2 C8 C11 -24.1(4) . . . . ? _olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)' _olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'