# Electronic Supplementary Material (ESI) for RSC Advances # 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_2012sot0132 #JJ-49 _chemical_compound_source 'Javier Jaramillo-Garcia' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H6 F12 O2, C16 H36 N, F' _chemical_formula_sum 'C28 H42 F13 N O2' _chemical_formula_weight 671.62 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.13(2) _cell_length_b 12.30(2) _cell_length_c 13.15(2) _cell_angle_alpha 111.064(3) _cell_angle_beta 102.557(11) _cell_angle_gamma 111.48(3) _cell_volume 1559(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3743 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 31.3 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_F_000 700 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.030 _exptl_absorpt_coefficient_mu 0.141 _shelx_estimated_absorpt_T_min 0.975 _shelx_estimated_absorpt_T_max 0.996 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.483 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_reflns_number 14351 _diffrn_reflns_av_unetI/netI 0.1264 _diffrn_reflns_av_R_equivalents 0.0838 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.169 _diffrn_reflns_theta_max 25.025 _diffrn_reflns_theta_full 27.500 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.767 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 0.767 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_point_group_measured_fraction_full 0.767 _reflns_number_total 5487 _reflns_number_gt 3244 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _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. These statistics refer to single and composite reflections containing twin component 1 only. ; _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refined as a 2-component twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5487 _refine_ls_number_parameters 452 _refine_ls_number_restraints 318 _refine_ls_R_factor_all 0.1735 _refine_ls_R_factor_gt 0.1271 _refine_ls_wR_factor_ref 0.3890 _refine_ls_wR_factor_gt 0.3357 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 F1 F 0.7054(5) 0.7142(5) 0.0204(4) 0.0421(13) Uani 1 1 d . . . . . N1A N 0.4694(12) 0.6621(14) 0.1968(12) 0.0330(15) Uani 0.506(8) 1 d D U P A 1 C13A C 0.5757(18) 0.628(2) 0.2352(15) 0.0352(19) Uani 0.506(8) 1 d D U P A 1 H13A H 0.5424 0.5314 0.1847 0.042 Uiso 0.506(8) 1 calc R U P A 1 H13B H 0.6504 0.6772 0.2208 0.042 Uiso 0.506(8) 1 calc R U P A 1 C14A C 0.622(2) 0.661(2) 0.3644(16) 0.038(2) Uani 0.506(8) 1 d D U P A 1 H14A H 0.5516 0.6045 0.3788 0.045 Uiso 0.506(8) 1 calc R U P A 1 H14B H 0.6504 0.7556 0.4167 0.045 Uiso 0.506(8) 1 calc R U P A 1 C15A C 0.737(2) 0.633(3) 0.3911(18) 0.039(2) Uani 0.506(8) 1 d D U P A 1 H15A H 0.8084 0.6911 0.3781 0.047 Uiso 0.506(8) 1 calc R U P A 1 H15B H 0.7094 0.5390 0.3367 0.047 Uiso 0.506(8) 1 calc R U P A 1 C16A C 0.786(3) 0.662(3) 0.5221(19) 0.042(3) Uani 0.506(8) 1 d D U P A 1 H16A H 0.8046 0.7522 0.5751 0.063 Uiso 0.506(8) 1 calc R U P A 1 H16B H 0.8650 0.6549 0.5419 0.063 Uiso 0.506(8) 1 calc R U P A 1 H16C H 0.7192 0.5968 0.5319 0.063 Uiso 0.506(8) 1 calc R U P A 1 C17A C 0.5161(17) 0.8091(17) 0.2642(16) 0.0343(18) Uani 0.506(8) 1 d D U P A 1 H17A H 0.4464 0.8263 0.2316 0.041 Uiso 0.506(8) 1 calc R U P A 1 H17B H 0.5304 0.8338 0.3482 0.041 Uiso 0.506(8) 1 calc R U P A 1 C18A C 0.6364(18) 0.8981(16) 0.262(2) 0.0329(19) Uani 0.506(8) 1 d D U P A 1 H18A H 0.6235 0.8749 0.1782 0.040 Uiso 0.506(8) 1 calc R U P A 1 H18B H 0.7076 0.8838 0.2961 0.040 Uiso 0.506(8) 1 calc R U P A 1 C19A C 0.6744(18) 1.0448(17) 0.3317(17) 0.032(2) Uani 0.506(8) 1 d D U P A 1 H19A H 0.6032 1.0579 0.2951 0.038 Uiso 0.506(8) 1 calc R U P A 1 H19B H 0.6820 1.0651 0.4137 0.038 Uiso 0.506(8) 1 calc R U P A 1 C20A C 0.7968(19) 1.1430(18) 0.3390(17) 0.034(3) Uani 0.506(8) 1 d D U P A 1 H20A H 0.8127 1.2337 0.3866 0.051 Uiso 0.506(8) 1 calc R U P A 1 H20B H 0.7896 1.1273 0.2588 0.051 Uiso 0.506(8) 1 calc R U P A 1 H20C H 0.8688 1.1328 0.3767 0.051 Uiso 0.506(8) 1 calc R U P A 1 C21A C 0.437(2) 0.618(2) 0.0633(13) 0.0342(18) Uani 0.506(8) 1 d D U P A 1 H21A H 0.4007 0.5203 0.0193 0.041 Uiso 0.506(8) 1 calc R U P A 1 H21B H 0.5184 0.6598 0.0538 0.041 Uiso 0.506(8) 1 calc R U P A 1 C22A C 0.340(3) 0.655(3) 0.0062(15) 0.034(2) Uani 0.506(8) 1 d D U P A 1 H22A H 0.2634 0.6271 0.0255 0.041 Uiso 0.506(8) 1 calc R U P A 1 H22B H 0.3814 0.7530 0.0372 0.041 Uiso 0.506(8) 1 calc R U P A 1 C23A C 0.300(3) 0.584(3) -0.1281(15) 0.033(3) Uani 0.506(8) 1 d D U P A 1 H23A H 0.2628 0.4863 -0.1576 0.040 Uiso 0.506(8) 1 calc R U P A 1 H23B H 0.3764 0.6146 -0.1468 0.040 Uiso 0.506(8) 1 calc R U P A 1 C24A C 0.198(3) 0.611(3) -0.1908(17) 0.035(3) Uani 0.506(8) 1 d D U P A 1 H24A H 0.1725 0.5633 -0.2770 0.052 Uiso 0.506(8) 1 calc R U P A 1 H24B H 0.2360 0.7072 -0.1633 0.052 Uiso 0.506(8) 1 calc R U P A 1 H24C H 0.1226 0.5805 -0.1721 0.052 Uiso 0.506(8) 1 calc R U P A 1 C25A C 0.3425(15) 0.5766(16) 0.2039(13) 0.0341(17) Uani 0.506(8) 1 d D U P A 1 H25A H 0.2686 0.5552 0.1360 0.041 Uiso 0.506(8) 1 calc R U P A 1 H25B H 0.3392 0.4911 0.1922 0.041 Uiso 0.506(8) 1 calc R U P A 1 C26A C 0.3217(15) 0.6340(16) 0.3146(13) 0.0347(18) Uani 0.506(8) 1 d D U P A 1 H26A H 0.3124 0.7133 0.3235 0.042 Uiso 0.506(8) 1 calc R U P A 1 H26B H 0.3965 0.6618 0.3852 0.042 Uiso 0.506(8) 1 calc R U P A 1 C27A C 0.1966(15) 0.5248(19) 0.3041(16) 0.036(2) Uani 0.506(8) 1 d D U P A 1 H27A H 0.2109 0.4509 0.3051 0.044 Uiso 0.506(8) 1 calc R U P A 1 H27B H 0.1255 0.4883 0.2271 0.044 Uiso 0.506(8) 1 calc R U P A 1 C28A C 0.156(2) 0.580(2) 0.4072(16) 0.037(3) Uani 0.506(8) 1 d D U P A 1 H28A H 0.0777 0.5085 0.3982 0.056 Uiso 0.506(8) 1 calc R U P A 1 H28B H 0.1390 0.6516 0.4048 0.056 Uiso 0.506(8) 1 calc R U P A 1 H28C H 0.2261 0.6163 0.4835 0.056 Uiso 0.506(8) 1 calc R U P A 1 N1B N 0.4890(13) 0.7090(15) 0.2316(13) 0.0330(15) Uani 0.494(8) 1 d D U P A 2 C13B C 0.5802(19) 0.657(2) 0.2669(15) 0.0352(19) Uani 0.494(8) 1 d D U P A 2 H13C H 0.5302 0.5579 0.2264 0.042 Uiso 0.494(8) 1 calc R U P A 2 H13D H 0.6485 0.6811 0.2367 0.042 Uiso 0.494(8) 1 calc R U P A 2 C14B C 0.644(2) 0.707(2) 0.3980(16) 0.038(2) Uani 0.494(8) 1 d D U P A 2 H14C H 0.5791 0.6706 0.4279 0.045 Uiso 0.494(8) 1 calc R U P A 2 H14D H 0.6865 0.8057 0.4419 0.045 Uiso 0.494(8) 1 calc R U P A 2 C15B C 0.746(3) 0.660(3) 0.4165(19) 0.039(2) Uani 0.494(8) 1 d D U P A 2 H15C H 0.7047 0.5627 0.3645 0.047 Uiso 0.494(8) 1 calc R U P A 2 H15D H 0.8154 0.7044 0.3936 0.047 Uiso 0.494(8) 1 calc R U P A 2 C16B C 0.806(3) 0.695(3) 0.548(2) 0.042(3) Uani 0.494(8) 1 d D U P A 2 H16D H 0.8467 0.7913 0.5993 0.063 Uiso 0.494(8) 1 calc R U P A 2 H16E H 0.8722 0.6666 0.5577 0.063 Uiso 0.494(8) 1 calc R U P A 2 H16F H 0.7386 0.6480 0.5694 0.063 Uiso 0.494(8) 1 calc R U P A 2 C17B C 0.5582(18) 0.8575(17) 0.2852(16) 0.0343(18) Uani 0.494(8) 1 d D U P A 2 H17C H 0.4945 0.8836 0.2568 0.041 Uiso 0.494(8) 1 calc R U P A 2 H17D H 0.5848 0.8954 0.3724 0.041 Uiso 0.494(8) 1 calc R U P A 2 C18B C 0.6729(19) 0.9240(17) 0.265(2) 0.0329(19) Uani 0.494(8) 1 d D U P A 2 H18C H 0.6505 0.8889 0.1781 0.040 Uiso 0.494(8) 1 calc R U P A 2 H18D H 0.7421 0.9068 0.2980 0.040 Uiso 0.494(8) 1 calc R U P A 2 C19B C 0.7197(19) 1.0738(18) 0.3249(17) 0.032(2) Uani 0.494(8) 1 d D U P A 2 H19C H 0.6530 1.0892 0.2837 0.038 Uiso 0.494(8) 1 calc R U P A 2 H19D H 0.7270 1.1035 0.4080 0.038 Uiso 0.494(8) 1 calc R U P A 2 C20B C 0.8451(19) 1.1583(19) 0.3272(17) 0.034(3) Uani 0.494(8) 1 d D U P A 2 H20D H 0.8661 1.2520 0.3665 0.051 Uiso 0.494(8) 1 calc R U P A 2 H20E H 0.8391 1.1312 0.2456 0.051 Uiso 0.494(8) 1 calc R U P A 2 H20F H 0.9131 1.1474 0.3712 0.051 Uiso 0.494(8) 1 calc R U P A 2 C21B C 0.436(2) 0.641(2) 0.0945(14) 0.0342(18) Uani 0.494(8) 1 d D U P A 2 H21C H 0.3942 0.5428 0.0631 0.041 Uiso 0.494(8) 1 calc R U P A 2 H21D H 0.5105 0.6661 0.0714 0.041 Uiso 0.494(8) 1 calc R U P A 2 C22B C 0.339(3) 0.674(3) 0.0344(15) 0.034(2) Uani 0.494(8) 1 d D U P A 2 H22C H 0.2627 0.6472 0.0548 0.041 Uiso 0.494(8) 1 calc R U P A 2 H22D H 0.3796 0.7717 0.0640 0.041 Uiso 0.494(8) 1 calc R U P A 2 C23B C 0.295(3) 0.601(3) -0.1013(15) 0.033(3) Uani 0.494(8) 1 d D U P A 2 H23C H 0.2509 0.5031 -0.1317 0.040 Uiso 0.494(8) 1 calc R U P A 2 H23D H 0.3709 0.6254 -0.1220 0.040 Uiso 0.494(8) 1 calc R U P A 2 C24B C 0.201(3) 0.640(3) -0.1585(17) 0.035(3) Uani 0.494(8) 1 d D U P A 2 H24D H 0.1728 0.5942 -0.2451 0.052 Uiso 0.494(8) 1 calc R U P A 2 H24E H 0.2452 0.7369 -0.1281 0.052 Uiso 0.494(8) 1 calc R U P A 2 H24F H 0.1255 0.6143 -0.1385 0.052 Uiso 0.494(8) 1 calc R U P A 2 C25B C 0.3781(15) 0.6687(15) 0.2749(14) 0.0341(17) Uani 0.494(8) 1 d D U P A 2 H25C H 0.4167 0.7151 0.3630 0.041 Uiso 0.494(8) 1 calc R U P A 2 H25D H 0.3198 0.7019 0.2499 0.041 Uiso 0.494(8) 1 calc R U P A 2 C26B C 0.2979(15) 0.5224(15) 0.2312(14) 0.0347(18) Uani 0.494(8) 1 d D U P A 2 H26C H 0.3462 0.4917 0.2745 0.042 Uiso 0.494(8) 1 calc R U P A 2 H26D H 0.2752 0.4707 0.1451 0.042 Uiso 0.494(8) 1 calc R U P A 2 C27B C 0.1729(16) 0.503(2) 0.2548(16) 0.036(2) Uani 0.494(8) 1 d D U P A 2 H27C H 0.1188 0.4076 0.2298 0.044 Uiso 0.494(8) 1 calc R U P A 2 H27D H 0.1226 0.5270 0.2053 0.044 Uiso 0.494(8) 1 calc R U P A 2 C28B C 0.202(2) 0.589(2) 0.3882(16) 0.037(3) Uani 0.494(8) 1 d D U P A 2 H28D H 0.1203 0.5714 0.3977 0.056 Uiso 0.494(8) 1 calc R U P A 2 H28E H 0.2523 0.6838 0.4127 0.056 Uiso 0.494(8) 1 calc R U P A 2 H28F H 0.2515 0.5655 0.4378 0.056 Uiso 0.494(8) 1 calc R U P A 2 F2 F -0.0394(6) -0.3069(6) 0.0192(5) 0.0611(17) Uani 1 1 d . . . . . F3 F -0.0303(6) -0.3822(6) 0.1417(6) 0.0604(17) Uani 1 1 d . . . . . F4 F 0.1463(6) -0.2452(6) 0.1477(6) 0.0578(16) Uani 1 1 d . . . . . F5 F 0.0411(5) -0.2109(7) 0.3734(5) 0.0577(16) Uani 1 1 d . . . . . F6 F 0.2123(5) -0.0711(7) 0.3766(6) 0.0657(19) Uani 1 1 d . . . . . F7 F 0.0736(6) -0.0158(7) 0.4183(5) 0.0647(18) Uani 1 1 d . . . . . F8 F 0.3012(5) 0.0258(6) -0.0140(4) 0.0448(14) Uani 1 1 d . . . . . F9 F 0.3852(5) -0.0149(5) 0.1193(5) 0.0452(14) Uani 1 1 d . . . . . F10 F 0.5065(5) 0.1342(5) 0.0870(5) 0.0473(14) Uani 1 1 d . . . . . F11 F 0.4597(5) 0.1660(5) 0.3537(4) 0.0446(13) Uani 1 1 d . . . . . F12 F 0.5955(5) 0.3019(5) 0.3179(4) 0.0426(13) Uani 1 1 d . . . . . F13 F 0.4644(5) 0.3516(5) 0.3866(4) 0.0488(15) Uani 1 1 d . . . . . O1 O -0.1185(6) -0.2068(7) 0.2043(6) 0.0424(16) Uani 1 1 d . . . . . H1 H -0.1672 -0.2329 0.1346 0.064 Uiso 1 1 calc R U . . . O2 O 0.4063(6) 0.2967(6) 0.1625(5) 0.0392(15) Uani 1 1 d . . . . . H2 H 0.3565 0.2718 0.0937 0.059 Uiso 1 1 calc R U . . . C1 C 0.0241(9) -0.2723(10) 0.1336(8) 0.039(2) Uani 1 1 d . . . . . C2 C 0.0855(8) -0.1126(10) 0.3480(8) 0.042(2) Uani 1 1 d . . . . . C3 C 0.0088(9) -0.1573(10) 0.2158(7) 0.040(2) Uani 1 1 d . . . . . C4 C 0.0621(8) -0.0398(9) 0.1910(7) 0.034(2) Uani 1 1 d . . . . . C5 C -0.0208(9) 0.0098(10) 0.1609(8) 0.043(2) Uani 1 1 d . . . . . H5 H -0.1067 -0.0285 0.1561 0.051 Uiso 1 1 calc R U . . . C6 C 0.0268(9) 0.1162(9) 0.1387(8) 0.041(2) Uani 1 1 d . . . . . H6 H -0.0280 0.1503 0.1173 0.049 Uiso 1 1 calc R U . . . C7 C 0.1524(10) 0.1737(10) 0.1469(7) 0.043(2) Uani 1 1 d . . . . . H7 H 0.1831 0.2469 0.1318 0.051 Uiso 1 1 calc R U . . . C8 C 0.2349(8) 0.1240(9) 0.1776(7) 0.037(2) Uani 1 1 d . . . . . C9 C 0.1883(9) 0.0208(9) 0.2013(7) 0.035(2) Uani 1 1 d . . . . . H9 H 0.2444 -0.0106 0.2257 0.042 Uiso 1 1 calc R U . . . C10 C 0.3737(7) 0.1892(8) 0.1838(7) 0.0275(18) Uani 1 1 d . . . . . C11 C 0.3923(9) 0.0833(9) 0.0940(7) 0.037(2) Uani 1 1 d . . . . . C12 C 0.4751(8) 0.2511(9) 0.3108(8) 0.036(2) Uani 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 F1 0.043(3) 0.053(3) 0.033(2) 0.021(2) 0.010(2) 0.028(2) N1A 0.037(3) 0.040(3) 0.030(3) 0.015(3) 0.013(2) 0.028(3) C13A 0.038(3) 0.040(4) 0.032(4) 0.014(3) 0.011(3) 0.030(3) C14A 0.041(3) 0.041(5) 0.032(5) 0.011(4) 0.010(3) 0.029(4) C15A 0.042(4) 0.041(6) 0.033(5) 0.012(4) 0.007(4) 0.031(4) C16A 0.045(6) 0.042(8) 0.032(6) 0.009(6) 0.005(5) 0.029(6) C17A 0.040(4) 0.039(4) 0.029(3) 0.015(3) 0.013(3) 0.026(3) C18A 0.038(5) 0.039(4) 0.029(3) 0.014(3) 0.015(3) 0.028(3) C19A 0.037(5) 0.039(4) 0.027(3) 0.013(3) 0.017(4) 0.027(3) C20A 0.038(7) 0.043(4) 0.026(4) 0.014(4) 0.017(5) 0.023(4) C21A 0.037(3) 0.042(4) 0.030(3) 0.013(3) 0.014(3) 0.029(3) C22A 0.036(3) 0.041(4) 0.030(4) 0.013(4) 0.013(4) 0.029(3) C23A 0.036(3) 0.040(5) 0.029(4) 0.013(4) 0.014(4) 0.027(3) C24A 0.036(4) 0.039(7) 0.031(6) 0.014(5) 0.011(5) 0.024(4) C25A 0.038(3) 0.040(4) 0.031(3) 0.015(3) 0.014(3) 0.028(3) C26A 0.039(3) 0.041(4) 0.031(3) 0.015(3) 0.014(3) 0.027(3) C27A 0.040(4) 0.042(4) 0.032(4) 0.016(4) 0.015(3) 0.026(3) C28A 0.043(6) 0.044(5) 0.033(5) 0.019(4) 0.018(4) 0.026(5) N1B 0.037(3) 0.040(3) 0.030(3) 0.015(3) 0.013(2) 0.028(3) C13B 0.038(3) 0.040(4) 0.032(4) 0.014(3) 0.011(3) 0.030(3) C14B 0.041(3) 0.041(5) 0.032(5) 0.011(4) 0.010(3) 0.029(4) C15B 0.042(4) 0.041(6) 0.033(5) 0.012(4) 0.007(4) 0.031(4) C16B 0.045(6) 0.042(8) 0.032(6) 0.009(6) 0.005(5) 0.029(6) C17B 0.040(4) 0.039(4) 0.029(3) 0.015(3) 0.013(3) 0.026(3) C18B 0.038(5) 0.039(4) 0.029(3) 0.014(3) 0.015(3) 0.028(3) C19B 0.037(5) 0.039(4) 0.027(3) 0.013(3) 0.017(4) 0.027(3) C20B 0.038(7) 0.043(4) 0.026(4) 0.014(4) 0.017(5) 0.023(4) C21B 0.037(3) 0.042(4) 0.030(3) 0.013(3) 0.014(3) 0.029(3) C22B 0.036(3) 0.041(4) 0.030(4) 0.013(4) 0.013(4) 0.029(3) C23B 0.036(3) 0.040(5) 0.029(4) 0.013(4) 0.014(4) 0.027(3) C24B 0.036(4) 0.039(7) 0.031(6) 0.014(5) 0.011(5) 0.024(4) C25B 0.038(3) 0.040(4) 0.031(3) 0.015(3) 0.014(3) 0.028(3) C26B 0.039(3) 0.041(4) 0.031(3) 0.015(3) 0.014(3) 0.027(3) C27B 0.040(4) 0.042(4) 0.032(4) 0.016(4) 0.015(3) 0.026(3) C28B 0.043(6) 0.044(5) 0.033(5) 0.019(4) 0.018(4) 0.026(5) F2 0.070(4) 0.073(4) 0.038(3) 0.015(3) 0.016(3) 0.047(3) F3 0.057(4) 0.059(4) 0.088(5) 0.043(4) 0.042(3) 0.036(3) F4 0.051(3) 0.060(4) 0.082(4) 0.036(3) 0.032(3) 0.041(3) F5 0.045(3) 0.083(4) 0.054(3) 0.052(3) 0.010(3) 0.026(3) F6 0.036(3) 0.107(5) 0.062(4) 0.061(4) 0.008(3) 0.030(3) F7 0.077(4) 0.083(5) 0.030(3) 0.022(3) 0.014(3) 0.044(4) F8 0.052(3) 0.063(4) 0.021(2) 0.016(2) 0.007(2) 0.039(3) F9 0.058(3) 0.052(3) 0.044(3) 0.026(3) 0.022(3) 0.040(3) F10 0.040(3) 0.049(3) 0.058(3) 0.022(3) 0.028(3) 0.025(3) F11 0.047(3) 0.053(3) 0.033(2) 0.027(2) 0.004(2) 0.024(3) F12 0.035(3) 0.056(3) 0.035(3) 0.025(2) 0.008(2) 0.022(2) F13 0.050(3) 0.051(3) 0.031(3) 0.008(2) 0.004(2) 0.030(3) O1 0.031(3) 0.071(5) 0.040(3) 0.037(3) 0.012(3) 0.033(3) O2 0.034(3) 0.047(4) 0.033(3) 0.016(3) 0.006(3) 0.023(3) C1 0.043(5) 0.050(6) 0.044(5) 0.030(5) 0.027(4) 0.028(5) C2 0.032(5) 0.060(7) 0.037(5) 0.027(5) 0.016(4) 0.020(5) C3 0.038(5) 0.070(7) 0.028(4) 0.029(4) 0.010(4) 0.038(5) C4 0.036(5) 0.047(5) 0.026(4) 0.017(4) 0.007(4) 0.030(4) C5 0.030(5) 0.063(7) 0.044(5) 0.034(5) 0.011(4) 0.026(5) C6 0.035(5) 0.049(6) 0.044(5) 0.026(5) 0.009(4) 0.028(4) C7 0.068(7) 0.042(5) 0.023(4) 0.014(4) 0.008(4) 0.040(5) C8 0.033(5) 0.044(5) 0.026(4) 0.012(4) 0.000(4) 0.025(4) C9 0.045(5) 0.045(5) 0.017(3) 0.014(4) 0.003(4) 0.032(4) C10 0.020(4) 0.039(5) 0.025(4) 0.019(4) 0.008(3) 0.013(3) C11 0.038(5) 0.042(5) 0.029(4) 0.019(4) 0.005(4) 0.021(4) C12 0.034(5) 0.036(5) 0.048(5) 0.024(4) 0.024(4) 0.019(4) _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 N1A C17A 1.501(18) . ? N1A C13A 1.537(14) . ? N1A C21A 1.546(16) . ? N1A C25A 1.559(18) . ? C13A C14A 1.513(18) . ? C14A C15A 1.551(16) . ? C15A C16A 1.552(17) . ? C17A C18A 1.48(2) . ? C18A C19A 1.525(17) . ? C19A C20A 1.49(2) . ? C21A C22A 1.552(15) . ? C22A C23A 1.524(17) . ? C23A C24A 1.538(15) . ? C25A C26A 1.495(17) . ? C26A C27A 1.55(2) . ? C27A C28A 1.55(2) . ? N1B C17B 1.494(18) . ? N1B C13B 1.539(14) . ? N1B C21B 1.543(16) . ? N1B C25B 1.557(18) . ? C13B C14B 1.503(17) . ? C14B C15B 1.553(16) . ? C15B C16B 1.547(17) . ? C17B C18B 1.47(2) . ? C18B C19B 1.527(17) . ? C19B C20B 1.48(2) . ? C21B C22B 1.544(15) . ? C22B C23B 1.536(17) . ? C23B C24B 1.546(15) . ? C25B C26B 1.499(18) . ? C26B C27B 1.563(19) . ? C27B C28B 1.56(2) . ? F2 C1 1.354(11) . ? F3 C1 1.324(11) . ? F4 C1 1.348(11) . ? F5 C2 1.325(11) . ? F6 C2 1.343(11) . ? F7 C2 1.299(12) . ? F8 C11 1.327(9) . ? F9 C11 1.342(11) . ? F10 C11 1.335(11) . ? F11 C12 1.333(10) . ? F12 C12 1.327(10) . ? F13 C12 1.351(10) . ? O1 C3 1.386(11) . ? O2 C10 1.383(10) . ? C1 C3 1.543(13) . ? C2 C3 1.557(12) . ? C3 C4 1.536(14) . ? C4 C9 1.385(13) . ? C4 C5 1.410(12) . ? C5 C6 1.388(13) . ? C6 C7 1.385(14) . ? C7 C8 1.410(12) . ? C8 C9 1.365(13) . ? C8 C10 1.545(12) . ? C10 C11 1.539(12) . ? C10 C12 1.546(12) . ? 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 C17A N1A C13A 111.7(12) . . ? C17A N1A C21A 109.6(11) . . ? C13A N1A C21A 104.7(11) . . ? C17A N1A C25A 112.5(12) . . ? C13A N1A C25A 111.7(12) . . ? C21A N1A C25A 106.2(12) . . ? C14A C13A N1A 114.4(12) . . ? C13A C14A C15A 107.6(13) . . ? C14A C15A C16A 109.4(15) . . ? C18A C17A N1A 116.0(12) . . ? C17A C18A C19A 111.7(13) . . ? C20A C19A C18A 116.1(13) . . ? N1A C21A C22A 114.5(12) . . ? C23A C22A C21A 107.8(12) . . ? C22A C23A C24A 110.4(13) . . ? C26A C25A N1A 118.2(12) . . ? C25A C26A C27A 107.9(13) . . ? C26A C27A C28A 111.9(15) . . ? C17B N1B C13B 111.9(12) . . ? C17B N1B C21B 111.2(12) . . ? C13B N1B C21B 104.3(11) . . ? C17B N1B C25B 108.2(12) . . ? C13B N1B C25B 109.7(12) . . ? C21B N1B C25B 111.4(12) . . ? C14B C13B N1B 115.4(13) . . ? C13B C14B C15B 107.5(13) . . ? C16B C15B C14B 110.9(15) . . ? C18B C17B N1B 119.9(13) . . ? C17B C18B C19B 108.5(13) . . ? C20B C19B C18B 115.6(14) . . ? N1B C21B C22B 115.4(12) . . ? C23B C22B C21B 110.1(12) . . ? C22B C23B C24B 108.8(13) . . ? C26B C25B N1B 116.1(12) . . ? C25B C26B C27B 106.5(13) . . ? C26B C27B C28B 113.2(15) . . ? F3 C1 F4 107.1(7) . . ? F3 C1 F2 105.4(8) . . ? F4 C1 F2 106.3(7) . . ? F3 C1 C3 112.8(8) . . ? F4 C1 C3 116.0(8) . . ? F2 C1 C3 108.6(7) . . ? F7 C2 F5 107.0(8) . . ? F7 C2 F6 108.0(8) . . ? F5 C2 F6 106.4(8) . . ? F7 C2 C3 110.1(8) . . ? F5 C2 C3 111.7(8) . . ? F6 C2 C3 113.4(7) . . ? O1 C3 C4 116.4(7) . . ? O1 C3 C1 108.8(8) . . ? C4 C3 C1 109.0(7) . . ? O1 C3 C2 103.2(7) . . ? C4 C3 C2 109.8(8) . . ? C1 C3 C2 109.3(7) . . ? C9 C4 C5 119.7(8) . . ? C9 C4 C3 122.5(7) . . ? C5 C4 C3 117.8(8) . . ? C6 C5 C4 118.1(9) . . ? C7 C6 C5 121.3(7) . . ? C6 C7 C8 120.2(9) . . ? C9 C8 C7 118.2(9) . . ? C9 C8 C10 123.1(7) . . ? C7 C8 C10 118.7(9) . . ? C8 C9 C4 122.3(7) . . ? O2 C10 C11 108.5(7) . . ? O2 C10 C8 115.1(6) . . ? C11 C10 C8 109.2(7) . . ? O2 C10 C12 102.6(6) . . ? C11 C10 C12 110.3(7) . . ? C8 C10 C12 110.9(6) . . ? F8 C11 F10 107.4(7) . . ? F8 C11 F9 106.7(7) . . ? F10 C11 F9 105.9(7) . . ? F8 C11 C10 110.1(7) . . ? F10 C11 C10 112.9(7) . . ? F9 C11 C10 113.5(7) . . ? F12 C12 F11 107.7(7) . . ? F12 C12 F13 107.4(7) . . ? F11 C12 F13 105.8(7) . . ? F12 C12 C10 112.5(7) . . ? F11 C12 C10 113.8(7) . . ? F13 C12 C10 109.3(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 F1 0.84 1.62 2.429(8) 161.2 1_445 O2 H2 F1 0.84 1.62 2.421(8) 157.4 2_665 _refine_diff_density_max 0.462 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.100 _shelxl_version_number 2012-9 _database_code_depnum_ccdc_archive 'CCDC 962265' ####################################################################### # # 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_2012nb110-mark _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H5 F12 O2, C8 H20 N' _chemical_formula_sum 'C20 H25 F12 N O2' _chemical_formula_weight 539.41 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 7.7525(6) _cell_length_b 14.2782(10) _cell_length_c 10.7005(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.110(7) _cell_angle_gamma 90.00 _cell_volume 1132.03(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4852 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9546 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_reflns_number 5314 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2669 _reflns_number_gt 2381 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material ? _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^ > 2\s(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. The hydrogen atoms of the hydroxyl groups are set to 50% occupancies because only one oxygen atom is protonated, but due to symmetry it is disordered over the 2 hydroxyl groups in the molecule ; _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^)+(0.0319P)^2^+0.3817P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2669 _refine_ls_number_parameters 203 _refine_ls_number_restraints 179 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _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 O1 O 0.07076(9) 0.49532(5) 0.11851(7) 0.01509(15) Uani 1 1 d U . . H1 H 0.0278 0.5028 0.0374 0.023 Uiso 0.50 1 calc PR . . F1 F 0.11315(9) 0.53636(5) 0.36844(6) 0.02193(15) Uani 1 1 d U . . F2 F 0.35959(9) 0.47644(5) 0.35043(6) 0.02547(16) Uani 1 1 d U . . F3 F 0.34571(9) 0.62380(4) 0.38825(6) 0.02422(16) Uani 1 1 d U . . F4 F 0.48878(8) 0.61743(5) 0.18698(7) 0.02513(16) Uani 1 1 d U . . F5 F 0.29876(9) 0.60580(5) -0.00509(7) 0.02723(17) Uani 1 1 d U . . F6 F 0.40279(9) 0.48198(5) 0.10493(7) 0.02727(17) Uani 1 1 d U . . C1 C 0.25188(14) 0.55185(7) 0.32006(10) 0.0171(2) Uani 1 1 d U . . C2 C 0.18029(12) 0.56909(7) 0.17057(9) 0.01300(19) Uani 1 1 d U . . C3 C 0.34431(13) 0.56883(7) 0.11486(10) 0.0182(2) Uani 1 1 d U . . C4 C 0.17749(18) 0.7500 0.16726(13) 0.0138(3) Uani 1 2 d SU . . H4 H 0.3056 0.7500 0.1916 0.017 Uiso 1 2 calc SR . . C5 C 0.08460(12) 0.66503(7) 0.14959(9) 0.01255(19) Uani 1 1 d U . . C6 C -0.10346(13) 0.66541(7) 0.11517(10) 0.0156(2) Uani 1 1 d U . . H6 H -0.1681 0.6080 0.1031 0.019 Uiso 1 1 calc R . . C7 C -0.19603(19) 0.7500 0.09861(15) 0.0183(3) Uani 1 2 d SU . . H7 H -0.3241 0.7500 0.0757 0.022 Uiso 1 2 calc SR . . N1 N -0.00459(19) 0.2580(15) 0.35658(14) 0.0108(19) Uani 0.50 1 d PU A -1 C8 C 0.0992(3) 0.19484(15) 0.2850(2) 0.0203(4) Uani 0.50 1 d PU A -1 H8A H 0.1540 0.1419 0.3429 0.024 Uiso 0.50 1 calc PR A -1 H8B H 0.0123 0.1684 0.2057 0.024 Uiso 0.50 1 calc PR A -1 C9 C 0.2462(3) 0.2460(14) 0.2455(2) 0.0282(9) Uani 0.50 1 d PU A -1 H9A H 0.3053 0.2026 0.2001 0.042 Uiso 0.50 1 calc PR A -1 H9B H 0.3355 0.2704 0.3237 0.042 Uiso 0.50 1 calc PR A -1 H9C H 0.1931 0.2980 0.1871 0.042 Uiso 0.50 1 calc PR A -1 C10 C 0.1221(3) 0.30476(14) 0.4715(2) 0.0177(4) Uani 0.50 1 d PU A -1 H10A H 0.0495 0.3392 0.5186 0.021 Uiso 0.50 1 calc PR A -1 H10B H 0.1920 0.3518 0.4386 0.021 Uiso 0.50 1 calc PR A -1 C11 C 0.2548(3) 0.2434(12) 0.5695(2) 0.0266(12) Uani 0.50 1 d PU A -1 H11A H 0.3307 0.2825 0.6396 0.040 Uiso 0.50 1 calc PR A -1 H11B H 0.3310 0.2099 0.5257 0.040 Uiso 0.50 1 calc PR A -1 H11C H 0.1886 0.1981 0.6067 0.040 Uiso 0.50 1 calc PR A -1 C12 C -0.1151(3) 0.32495(16) 0.2602(2) 0.0207(4) Uani 0.50 1 d PU A -1 H12A H -0.1885 0.2891 0.1838 0.025 Uiso 0.50 1 calc PR A -1 H12B H -0.0329 0.3659 0.2294 0.025 Uiso 0.50 1 calc PR A -1 C13 C -0.2399(12) 0.3861(6) 0.3093(10) 0.0281(13) Uani 0.50 1 d PU A -1 H13A H -0.3021 0.4301 0.2404 0.042 Uiso 0.50 1 calc PR A -1 H13B H -0.1696 0.4212 0.3862 0.042 Uiso 0.50 1 calc PR A -1 H13C H -0.3290 0.3469 0.3332 0.042 Uiso 0.50 1 calc PR A -1 C14 C -0.1235(3) 0.19009(18) 0.4092(2) 0.0260(5) Uani 0.50 1 d PU A -1 H14A H -0.0432 0.1440 0.4674 0.031 Uiso 0.50 1 calc PR A -1 H14B H -0.1832 0.2266 0.4633 0.031 Uiso 0.50 1 calc PR A -1 C15 C -0.2668(13) 0.1372(6) 0.3077(10) 0.0333(17) Uani 0.50 1 d PU A -1 H15A H -0.3387 0.0999 0.3510 0.050 Uiso 0.50 1 calc PR A -1 H15B H -0.2093 0.0956 0.2589 0.050 Uiso 0.50 1 calc PR A -1 H15C H -0.3454 0.1816 0.2474 0.050 Uiso 0.50 1 calc PR A -1 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 O1 0.0174(3) 0.0124(3) 0.0146(3) -0.0025(3) 0.0032(3) -0.0037(3) F1 0.0302(3) 0.0214(3) 0.0167(3) 0.0000(2) 0.0107(3) -0.0022(3) F2 0.0273(3) 0.0195(3) 0.0246(3) 0.0043(3) -0.0002(3) 0.0070(3) F3 0.0305(3) 0.0193(3) 0.0167(3) -0.0028(2) -0.0027(3) -0.0060(3) F4 0.0140(3) 0.0226(3) 0.0390(4) -0.0057(3) 0.0082(3) -0.0032(2) F5 0.0309(4) 0.0335(4) 0.0231(3) 0.0026(3) 0.0169(3) 0.0015(3) F6 0.0252(3) 0.0178(3) 0.0440(4) -0.0067(3) 0.0182(3) 0.0032(2) C1 0.0196(5) 0.0135(5) 0.0167(5) -0.0007(4) 0.0029(4) -0.0005(4) C2 0.0129(4) 0.0125(4) 0.0135(4) -0.0015(4) 0.0038(3) -0.0008(3) C3 0.0170(4) 0.0158(5) 0.0230(5) -0.0029(4) 0.0076(4) -0.0001(4) C4 0.0123(6) 0.0155(7) 0.0135(6) 0.000 0.0034(5) 0.000 C5 0.0138(4) 0.0132(5) 0.0109(4) -0.0002(3) 0.0039(3) 0.0013(3) C6 0.0142(4) 0.0161(5) 0.0172(5) -0.0019(4) 0.0056(4) -0.0030(3) C7 0.0120(6) 0.0206(7) 0.0228(7) 0.000 0.0057(5) 0.000 N1 0.0151(5) 0.005(6) 0.0117(5) 0.0000(10) 0.0034(4) -0.0014(10) C8 0.0268(10) 0.0153(10) 0.0199(10) -0.0030(8) 0.0084(8) 0.0023(8) C9 0.0258(8) 0.036(3) 0.0283(9) 0.001(4) 0.0164(7) 0.003(4) C10 0.0185(9) 0.0172(10) 0.0160(9) -0.0031(8) 0.0029(7) -0.0023(7) C11 0.0219(8) 0.032(4) 0.0207(8) 0.001(2) -0.0025(6) -0.001(2) C12 0.0212(10) 0.0248(11) 0.0158(10) 0.0047(8) 0.0049(8) 0.0077(8) C13 0.021(2) 0.040(4) 0.0219(18) 0.007(2) 0.0051(15) 0.016(2) C14 0.0270(11) 0.0342(13) 0.0164(10) 0.0014(9) 0.0058(8) -0.0158(10) C15 0.035(3) 0.042(4) 0.0246(19) -0.004(2) 0.0110(19) -0.018(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 C2 1.3646(11) . ? O1 H1 0.8400 . ? F1 C1 1.3422(12) . ? F2 C1 1.3426(12) . ? F3 C1 1.3433(12) . ? F4 C3 1.3502(12) . ? F5 C3 1.3357(13) . ? F6 C3 1.3353(12) . ? C1 C2 1.5508(13) . ? C2 C5 1.5425(13) . ? C2 C3 1.5551(13) . ? C4 C5 1.3951(11) . ? C4 C5 1.3951(11) 4_575 ? C4 H4 0.9500 . ? C5 C6 1.3947(13) . ? C6 C7 1.3894(12) . ? C6 H6 0.9500 . ? C7 C6 1.3894(12) 4_575 ? C7 H7 0.9500 . ? N1 C12 1.481(14) . ? N1 C10 1.488(10) . ? N1 C8 1.552(13) . ? N1 C14 1.553(14) . ? C8 C9 1.514(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.513(11) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.508(11) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.508(10) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C2 O1 H1 109.5 . . ? F1 C1 F2 106.64(8) . . ? F1 C1 F3 106.49(8) . . ? F2 C1 F3 106.44(8) . . ? F1 C1 C2 109.86(8) . . ? F2 C1 C2 112.66(8) . . ? F3 C1 C2 114.28(8) . . ? O1 C2 C5 114.28(8) . . ? O1 C2 C1 106.83(8) . . ? C5 C2 C1 107.57(8) . . ? O1 C2 C3 108.81(8) . . ? C5 C2 C3 111.02(8) . . ? C1 C2 C3 108.07(8) . . ? F6 C3 F5 106.89(8) . . ? F6 C3 F4 106.19(8) . . ? F5 C3 F4 106.64(8) . . ? F6 C3 C2 111.58(8) . . ? F5 C3 C2 110.65(8) . . ? F4 C3 C2 114.46(8) . . ? C5 C4 C5 120.85(12) . 4_575 ? C5 C4 H4 119.6 . . ? C5 C4 H4 119.6 4_575 . ? C6 C5 C4 119.35(9) . . ? C6 C5 C2 117.55(8) . . ? C4 C5 C2 123.07(8) . . ? C7 C6 C5 119.85(10) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C6 120.75(13) 4_575 . ? C6 C7 H7 119.6 4_575 . ? C6 C7 H7 119.6 . . ? C12 N1 C10 113.1(14) . . ? C12 N1 C8 108.01(16) . . ? C10 N1 C8 110.9(2) . . ? C12 N1 C14 111.84(15) . . ? C10 N1 C14 107.4(3) . . ? C8 N1 C14 105.4(13) . . ? C9 C8 N1 113.6(9) . . ? C9 C8 H8A 108.9 . . ? N1 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? N1 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C11 117.5(9) . . ? N1 C10 H10A 107.9 . . ? C11 C10 H10A 107.9 . . ? N1 C10 H10B 107.9 . . ? C11 C10 H10B 107.9 . . ? H10A C10 H10B 107.2 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C13 115.5(5) . . ? N1 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? N1 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 N1 116.2(5) . . ? C15 C14 H14A 108.2 . . ? N1 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? N1 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 F1 C1 C2 O1 -53.05(10) . . . . ? F2 C1 C2 O1 65.68(10) . . . . ? F3 C1 C2 O1 -172.66(8) . . . . ? F1 C1 C2 C5 70.07(10) . . . . ? F2 C1 C2 C5 -171.20(8) . . . . ? F3 C1 C2 C5 -49.54(11) . . . . ? F1 C1 C2 C3 -169.99(8) . . . . ? F2 C1 C2 C3 -51.26(11) . . . . ? F3 C1 C2 C3 70.40(10) . . . . ? O1 C2 C3 F6 -39.13(11) . . . . ? C5 C2 C3 F6 -165.74(8) . . . . ? C1 C2 C3 F6 76.51(10) . . . . ? O1 C2 C3 F5 79.74(10) . . . . ? C5 C2 C3 F5 -46.86(11) . . . . ? C1 C2 C3 F5 -164.61(8) . . . . ? O1 C2 C3 F4 -159.75(8) . . . . ? C5 C2 C3 F4 73.65(11) . . . . ? C1 C2 C3 F4 -44.10(11) . . . . ? C5 C4 C5 C6 -0.69(19) 4_575 . . . ? C5 C4 C5 C2 -178.68(7) 4_575 . . . ? O1 C2 C5 C6 17.35(12) . . . . ? C1 C2 C5 C6 -101.08(10) . . . . ? C3 C2 C5 C6 140.87(9) . . . . ? O1 C2 C5 C4 -164.63(10) . . . . ? C1 C2 C5 C4 76.95(12) . . . . ? C3 C2 C5 C4 -41.10(13) . . . . ? C4 C5 C6 C7 0.15(16) . . . . ? C2 C5 C6 C7 178.25(10) . . . . ? C5 C6 C7 C6 0.4(2) . . . 4_575 ? C12 N1 C8 C9 69.8(7) . . . . ? C10 N1 C8 C9 -54.6(11) . . . . ? C14 N1 C8 C9 -170.5(3) . . . . ? C12 N1 C10 C11 -174.00(19) . . . . ? C8 N1 C10 C11 -52.5(10) . . . . ? C14 N1 C10 C11 62.2(8) . . . . ? C10 N1 C12 C13 -62.6(5) . . . . ? C8 N1 C12 C13 174.3(6) . . . . ? C14 N1 C12 C13 58.7(11) . . . . ? C12 N1 C14 C15 53.5(12) . . . . ? C10 N1 C14 C15 178.1(6) . . . . ? C8 N1 C14 C15 -63.6(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O1 0.84 1.62 2.4530(14) 172.3 3_565 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.421 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 962266' ####################################################################### # # 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_2012nb113 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H6 F12 O2, C16 H36 N, Cl' _chemical_formula_sum 'C28 H42 Cl F12 N O2' _chemical_formula_weight 688.08 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.867(9) _cell_length_b 12.175(8) _cell_length_c 14.662(12) _cell_angle_alpha 111.01(4) _cell_angle_beta 102.34(7) _cell_angle_gamma 101.96(5) _cell_volume 1681(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4492 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 31.2 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9278 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12684 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0711 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5895 _reflns_number_gt 4279 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0426P)^2^+0.0000P] 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 5895 _refine_ls_number_parameters 405 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _refine_ls_shift/su_max 0.006 _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 H100 H 0.719(2) 0.162(2) -0.177(2) 0.070(9) Uiso 1 1 d . . . H101 H 1.225(2) 0.647(2) 0.326(2) 0.068(9) Uiso 1 1 d . . . C13 C 0.59986(18) 1.00836(16) 0.29298(16) 0.0251(5) Uani 1 1 d . . . H13A H 0.6073 0.9765 0.3466 0.030 Uiso 1 1 calc R . . H13B H 0.5046 0.9823 0.2541 0.030 Uiso 1 1 calc R . . C14 C 0.6702(2) 0.94674(17) 0.21932(16) 0.0280(5) Uani 1 1 d . . . H14A H 0.7652 0.9689 0.2573 0.034 Uiso 1 1 calc R . . H14B H 0.6638 0.9772 0.1648 0.034 Uiso 1 1 calc R . . C15 C 0.6078(2) 0.80581(18) 0.17015(17) 0.0326(5) Uani 1 1 d . . . H15A H 0.6188 0.7757 0.2249 0.039 Uiso 1 1 calc R . . H15B H 0.5116 0.7848 0.1365 0.039 Uiso 1 1 calc R . . C16 C 0.6690(2) 0.7392(2) 0.09050(18) 0.0405(6) Uani 1 1 d . . . H16A H 0.6260 0.6496 0.0618 0.061 Uiso 1 1 calc R . . H16B H 0.7640 0.7584 0.1236 0.061 Uiso 1 1 calc R . . H16C H 0.6563 0.7668 0.0351 0.061 Uiso 1 1 calc R . . C17 C 0.63169(19) 1.20056(17) 0.26483(15) 0.0253(5) Uani 1 1 d . . . H17A H 0.6944 1.1808 0.2261 0.030 Uiso 1 1 calc R . . H17B H 0.5409 1.1561 0.2157 0.030 Uiso 1 1 calc R . . C18 C 0.65195(19) 1.33924(17) 0.30404(16) 0.0259(5) Uani 1 1 d . . . H18A H 0.5832 1.3595 0.3360 0.031 Uiso 1 1 calc R . . H18B H 0.7397 1.3854 0.3573 0.031 Uiso 1 1 calc R . . C19 C 0.6436(2) 1.37845(19) 0.21589(18) 0.0363(6) Uani 1 1 d . . . H19A H 0.5553 1.3326 0.1634 0.044 Uiso 1 1 calc R . . H19B H 0.7110 1.3560 0.1832 0.044 Uiso 1 1 calc R . . C20 C 0.6659(2) 1.51775(19) 0.25183(19) 0.0411(6) Uani 1 1 d . . . H20A H 0.6594 1.5386 0.1927 0.062 Uiso 1 1 calc R . . H20B H 0.7541 1.5635 0.3027 0.062 Uiso 1 1 calc R . . H20C H 0.5984 1.5402 0.2831 0.062 Uiso 1 1 calc R . . C21 C 0.79752(17) 1.19771(18) 0.40881(15) 0.0237(5) Uani 1 1 d . . . H21A H 0.8490 1.1832 0.3599 0.028 Uiso 1 1 calc R . . H21B H 0.8225 1.2883 0.4491 0.028 Uiso 1 1 calc R . . C22 C 0.83851(18) 1.14024(18) 0.48228(15) 0.0250(5) Uani 1 1 d . . . H22A H 0.8231 1.0509 0.4426 0.030 Uiso 1 1 calc R . . H22B H 0.7837 1.1489 0.5289 0.030 Uiso 1 1 calc R . . C23 C 0.98574(18) 1.20399(19) 0.54617(16) 0.0285(5) Uani 1 1 d . . . H23A H 1.0406 1.1895 0.4998 0.034 Uiso 1 1 calc R . . H23B H 1.0023 1.2944 0.5810 0.034 Uiso 1 1 calc R . . C24 C 1.0266(2) 1.15514(19) 0.62675(16) 0.0333(5) Uani 1 1 d . . . H24A H 1.1209 1.1969 0.6657 0.050 Uiso 1 1 calc R . . H24B H 1.0111 1.0658 0.5924 0.050 Uiso 1 1 calc R . . H24C H 0.9740 1.1713 0.6739 0.050 Uiso 1 1 calc R . . C25 C 0.57047(18) 1.19394(18) 0.42036(15) 0.0245(5) Uani 1 1 d . . . H25A H 0.5811 1.1557 0.4697 0.029 Uiso 1 1 calc R . . H25B H 0.6091 1.2847 0.4604 0.029 Uiso 1 1 calc R . . C26 C 0.42205(18) 1.16349(19) 0.36773(16) 0.0277(5) Uani 1 1 d . . . H26A H 0.3798 1.0726 0.3356 0.033 Uiso 1 1 calc R . . H26B H 0.4100 1.1929 0.3126 0.033 Uiso 1 1 calc R . . C27 C 0.3542(2) 1.22460(19) 0.44509(17) 0.0325(5) Uani 1 1 d . . . H27A H 0.4016 1.3146 0.4809 0.039 Uiso 1 1 calc R . . H27B H 0.2623 1.2133 0.4069 0.039 Uiso 1 1 calc R . . C28 C 0.3507(2) 1.1731(2) 0.52443(19) 0.0453(7) Uani 1 1 d . . . H28A H 0.3072 1.2164 0.5716 0.068 Uiso 1 1 calc R . . H28B H 0.4414 1.1850 0.5634 0.068 Uiso 1 1 calc R . . H28C H 0.3012 1.0846 0.4898 0.068 Uiso 1 1 calc R . . N1 N 0.65008(15) 1.15003(14) 0.34669(12) 0.0214(4) Uani 1 1 d . . . Cl1 Cl 0.30946(5) 0.79802(5) 0.30285(4) 0.03147(16) Uani 1 1 d . . . C1 C 0.97858(18) 0.31296(17) 0.11678(15) 0.0225(5) Uani 1 1 d . . . H1 H 1.0095 0.2506 0.1292 0.027 Uiso 1 1 calc R . . C2 C 0.87599(18) 0.27978(17) 0.02637(15) 0.0216(5) Uani 1 1 d . . . C3 C 0.83214(18) 0.37189(18) 0.00782(16) 0.0249(5) Uani 1 1 d . . . H3 H 0.7625 0.3508 -0.0531 0.030 Uiso 1 1 calc R . . C4 C 0.89114(19) 0.49531(18) 0.07919(16) 0.0271(5) Uani 1 1 d . . . H4 H 0.8621 0.5581 0.0658 0.033 Uiso 1 1 calc R . . C5 C 0.99203(19) 0.52783(18) 0.16987(16) 0.0253(5) Uani 1 1 d . . . H5 H 1.0302 0.6120 0.2182 0.030 Uiso 1 1 calc R . . C6 C 1.03663(18) 0.43685(17) 0.18940(15) 0.0209(5) Uani 1 1 d . . . C7 C 0.81278(18) 0.14321(17) -0.05355(15) 0.0225(5) Uani 1 1 d . . . C8 C 0.9185(2) 0.09597(18) -0.09787(16) 0.0293(5) Uani 1 1 d . . . C9 C 0.7499(2) 0.06278(18) -0.00394(16) 0.0267(5) Uani 1 1 d . . . C10 C 1.14803(18) 0.47210(17) 0.28974(15) 0.0222(5) Uani 1 1 d . . . C11 C 1.2699(2) 0.43495(19) 0.26582(17) 0.0306(5) Uani 1 1 d . . . C12 C 1.0952(2) 0.41050(18) 0.35542(16) 0.0270(5) Uani 1 1 d . . . O1 O 0.70404(13) 0.12352(13) -0.13501(11) 0.0277(4) Uani 1 1 d . . . O2 O 1.19135(13) 0.59800(12) 0.35685(11) 0.0263(4) Uani 1 1 d . . . F1 F 0.96463(11) 0.16519(11) -0.14490(9) 0.0372(3) Uani 1 1 d . . . F2 F 0.87039(12) -0.02222(11) -0.16939(10) 0.0454(4) Uani 1 1 d . . . F3 F 1.02442(11) 0.10345(10) -0.02645(9) 0.0325(3) Uani 1 1 d . . . F4 F 0.69479(11) -0.05759(10) -0.07090(9) 0.0363(3) Uani 1 1 d . . . F5 F 0.83682(11) 0.06653(10) 0.07867(9) 0.0296(3) Uani 1 1 d . . . F6 F 0.65240(11) 0.10164(10) 0.02734(9) 0.0320(3) Uani 1 1 d . . . F7 F 1.31138(12) 0.48552(12) 0.20601(10) 0.0419(3) Uani 1 1 d . . . F8 F 1.24608(11) 0.31174(11) 0.21669(10) 0.0416(4) Uani 1 1 d . . . F9 F 1.37344(11) 0.47496(11) 0.35210(10) 0.0421(3) Uani 1 1 d . . . F10 F 1.05473(12) 0.28539(10) 0.30860(9) 0.0370(3) Uani 1 1 d . . . F11 F 0.99026(11) 0.44453(11) 0.37619(10) 0.0377(3) Uani 1 1 d . . . F12 F 1.18623(11) 0.44389(10) 0.44673(9) 0.0364(3) Uani 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 C13 0.0198(10) 0.0198(11) 0.0281(13) 0.0082(9) 0.0029(9) -0.0007(9) C14 0.0268(11) 0.0264(12) 0.0274(13) 0.0107(10) 0.0074(10) 0.0038(9) C15 0.0280(12) 0.0248(12) 0.0400(15) 0.0113(10) 0.0079(10) 0.0058(9) C16 0.0487(15) 0.0295(13) 0.0412(15) 0.0111(11) 0.0151(12) 0.0137(11) C17 0.0267(11) 0.0268(12) 0.0218(12) 0.0133(9) 0.0058(9) 0.0036(9) C18 0.0244(11) 0.0259(12) 0.0270(13) 0.0118(10) 0.0081(9) 0.0062(9) C19 0.0440(14) 0.0341(13) 0.0380(15) 0.0216(11) 0.0141(11) 0.0137(11) C20 0.0430(14) 0.0352(14) 0.0555(17) 0.0273(12) 0.0204(13) 0.0128(11) C21 0.0186(10) 0.0236(11) 0.0233(12) 0.0079(9) 0.0037(9) 0.0024(8) C22 0.0226(11) 0.0249(11) 0.0246(12) 0.0093(9) 0.0057(9) 0.0058(9) C23 0.0235(11) 0.0326(12) 0.0275(13) 0.0129(10) 0.0055(10) 0.0077(9) C24 0.0295(12) 0.0364(13) 0.0301(13) 0.0120(10) 0.0045(10) 0.0112(10) C25 0.0245(11) 0.0263(12) 0.0216(12) 0.0095(9) 0.0079(9) 0.0063(9) C26 0.0210(11) 0.0307(12) 0.0271(13) 0.0120(10) 0.0042(9) 0.0038(9) C27 0.0235(11) 0.0326(13) 0.0395(14) 0.0154(11) 0.0067(10) 0.0078(10) C28 0.0350(13) 0.0685(18) 0.0477(17) 0.0351(14) 0.0186(12) 0.0214(13) N1 0.0209(9) 0.0204(9) 0.0198(10) 0.0082(7) 0.0048(7) 0.0023(7) Cl1 0.0299(3) 0.0321(3) 0.0287(3) 0.0165(3) 0.0049(2) 0.0000(2) C1 0.0197(10) 0.0222(11) 0.0244(12) 0.0099(9) 0.0062(9) 0.0048(9) C2 0.0199(10) 0.0236(11) 0.0203(12) 0.0082(9) 0.0074(9) 0.0052(9) C3 0.0214(11) 0.0291(12) 0.0222(12) 0.0125(10) 0.0030(9) 0.0049(9) C4 0.0269(11) 0.0256(12) 0.0326(13) 0.0154(10) 0.0091(10) 0.0100(9) C5 0.0252(11) 0.0203(11) 0.0275(13) 0.0077(9) 0.0088(9) 0.0050(9) C6 0.0176(10) 0.0238(11) 0.0197(11) 0.0079(9) 0.0074(9) 0.0042(8) C7 0.0208(10) 0.0240(11) 0.0163(11) 0.0067(9) 0.0016(9) 0.0016(9) C8 0.0300(12) 0.0249(12) 0.0256(13) 0.0080(10) 0.0061(10) 0.0016(10) C9 0.0258(12) 0.0244(12) 0.0218(12) 0.0058(10) 0.0030(10) 0.0038(9) C10 0.0212(11) 0.0194(11) 0.0204(12) 0.0066(9) 0.0039(9) 0.0014(8) C11 0.0258(12) 0.0292(13) 0.0286(13) 0.0091(10) 0.0027(10) 0.0038(10) C12 0.0267(12) 0.0229(12) 0.0231(13) 0.0077(9) 0.0010(10) 0.0021(9) O1 0.0227(8) 0.0315(9) 0.0212(9) 0.0113(7) 0.0005(6) -0.0009(6) O2 0.0288(8) 0.0201(8) 0.0215(8) 0.0053(6) 0.0058(6) -0.0010(6) F1 0.0343(7) 0.0521(8) 0.0350(8) 0.0256(7) 0.0178(6) 0.0126(6) F2 0.0414(8) 0.0332(8) 0.0376(8) -0.0066(6) 0.0131(6) 0.0021(6) F3 0.0314(7) 0.0335(7) 0.0318(7) 0.0124(6) 0.0082(6) 0.0130(5) F4 0.0443(7) 0.0225(7) 0.0283(7) 0.0069(6) 0.0058(6) -0.0042(6) F5 0.0307(7) 0.0296(7) 0.0255(7) 0.0144(5) 0.0031(5) 0.0040(5) F6 0.0278(7) 0.0394(7) 0.0332(8) 0.0187(6) 0.0137(6) 0.0090(6) F7 0.0351(7) 0.0547(9) 0.0429(9) 0.0236(7) 0.0208(6) 0.0137(6) F8 0.0314(7) 0.0338(8) 0.0471(9) 0.0051(6) 0.0058(6) 0.0136(6) F9 0.0246(7) 0.0527(9) 0.0352(8) 0.0122(6) -0.0021(6) 0.0076(6) F10 0.0478(8) 0.0206(7) 0.0309(8) 0.0111(6) 0.0019(6) -0.0020(6) F11 0.0327(7) 0.0437(8) 0.0452(9) 0.0250(7) 0.0194(6) 0.0097(6) F12 0.0388(7) 0.0363(7) 0.0240(7) 0.0139(6) -0.0015(6) 0.0010(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C13 C14 1.524(3) . ? C13 N1 1.532(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.532(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.530(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.525(3) . ? C17 N1 1.529(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.522(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.532(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.521(3) . ? C21 N1 1.532(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.537(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.528(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.533(3) . ? C25 N1 1.542(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.537(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.510(3) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C1 C2 1.400(3) . ? C1 C6 1.405(3) . ? C1 H1 0.9500 . ? C2 C3 1.394(3) . ? C2 C7 1.548(3) . ? C3 C4 1.397(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C4 H4 0.9500 . ? C5 C6 1.391(3) . ? C5 H5 0.9500 . ? C6 C10 1.544(3) . ? C7 O1 1.398(3) . ? C7 C8 1.548(3) . ? C7 C9 1.550(3) . ? C8 F3 1.343(3) . ? C8 F2 1.347(3) . ? C8 F1 1.351(2) . ? C9 F5 1.347(3) . ? C9 F6 1.348(2) . ? C9 F4 1.350(3) . ? C10 O2 1.400(3) . ? C10 C12 1.547(3) . ? C10 C11 1.554(3) . ? C11 F7 1.339(2) . ? C11 F8 1.349(3) . ? C11 F9 1.351(3) . ? C12 F12 1.346(3) . ? C12 F11 1.349(2) . ? C12 F10 1.352(2) . ? O1 H100 0.92(3) . ? O2 H101 0.93(2) . ? 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 C14 C13 N1 116.42(16) . . ? C14 C13 H13A 108.2 . . ? N1 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? N1 C13 H13B 108.2 . . ? H13A C13 H13B 107.3 . . ? C13 C14 C15 110.47(17) . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C14 112.86(18) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 N1 116.14(17) . . ? C18 C17 H17A 108.3 . . ? N1 C17 H17A 108.3 . . ? C18 C17 H17B 108.3 . . ? N1 C17 H17B 108.3 . . ? H17A C17 H17B 107.4 . . ? C19 C18 C17 110.39(18) . . ? C19 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? C19 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C18 C19 C20 112.4(2) . . ? C18 C19 H19A 109.1 . . ? C20 C19 H19A 109.1 . . ? C18 C19 H19B 109.1 . . ? C20 C19 H19B 109.1 . . ? H19A C19 H19B 107.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 N1 115.86(16) . . ? C22 C21 H21A 108.3 . . ? N1 C21 H21A 108.3 . . ? C22 C21 H21B 108.3 . . ? N1 C21 H21B 108.3 . . ? H21A C21 H21B 107.4 . . ? C21 C22 C23 110.45(16) . . ? C21 C22 H22A 109.6 . . ? C23 C22 H22A 109.6 . . ? C21 C22 H22B 109.6 . . ? C23 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? C24 C23 C22 111.45(17) . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 N1 114.95(18) . . ? C26 C25 H25A 108.5 . . ? N1 C25 H25A 108.5 . . ? C26 C25 H25B 108.5 . . ? N1 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? C25 C26 C27 111.30(19) . . ? C25 C26 H26A 109.4 . . ? C27 C26 H26A 109.4 . . ? C25 C26 H26B 109.4 . . ? C27 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C28 C27 C26 113.59(19) . . ? C28 C27 H27A 108.8 . . ? C26 C27 H27A 108.8 . . ? C28 C27 H27B 108.8 . . ? C26 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C17 N1 C21 108.37(15) . . ? C17 N1 C13 108.70(16) . . ? C21 N1 C13 111.29(16) . . ? C17 N1 C25 111.03(15) . . ? C21 N1 C25 108.94(16) . . ? C13 N1 C25 108.52(15) . . ? C2 C1 C6 121.20(19) . . ? C2 C1 H1 119.4 . . ? C6 C1 H1 119.4 . . ? C3 C2 C1 119.18(18) . . ? C3 C2 C7 119.84(18) . . ? C1 C2 C7 120.97(18) . . ? C2 C3 C4 119.68(19) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.99(19) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 119.92(19) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 119.02(18) . . ? C5 C6 C10 120.22(17) . . ? C1 C6 C10 120.76(18) . . ? O1 C7 C2 114.13(17) . . ? O1 C7 C8 108.87(17) . . ? C2 C7 C8 109.65(16) . . ? O1 C7 C9 101.92(16) . . ? C2 C7 C9 110.21(18) . . ? C8 C7 C9 111.90(17) . . ? F3 C8 F2 106.96(18) . . ? F3 C8 F1 106.47(16) . . ? F2 C8 F1 106.41(19) . . ? F3 C8 C7 113.99(18) . . ? F2 C8 C7 113.22(17) . . ? F1 C8 C7 109.31(17) . . ? F5 C9 F6 107.24(17) . . ? F5 C9 F4 106.72(17) . . ? F6 C9 F4 106.89(16) . . ? F5 C9 C7 113.48(17) . . ? F6 C9 C7 110.04(17) . . ? F4 C9 C7 112.13(18) . . ? O2 C10 C6 114.20(17) . . ? O2 C10 C12 102.19(17) . . ? C6 C10 C12 110.02(16) . . ? O2 C10 C11 108.27(16) . . ? C6 C10 C11 110.89(17) . . ? C12 C10 C11 110.96(17) . . ? F7 C11 F8 106.96(19) . . ? F7 C11 F9 106.97(17) . . ? F8 C11 F9 106.17(17) . . ? F7 C11 C10 110.15(17) . . ? F8 C11 C10 114.06(17) . . ? F9 C11 C10 112.13(19) . . ? F12 C12 F11 106.70(18) . . ? F12 C12 F10 106.67(16) . . ? F11 C12 F10 106.92(17) . . ? F12 C12 C10 112.55(17) . . ? F11 C12 C10 110.18(16) . . ? F10 C12 C10 113.43(18) . . ? C7 O1 H100 117.3(16) . . ? C10 O2 H101 111.7(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H100 Cl1 0.92(3) 2.05(3) 2.929(3) 160(2) 2_665 O2 H101 Cl1 0.92(2) 2.06(2) 2.954(2) 163(2) 1_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.296 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 962267'