#------------------------------------------------------------------------------ #$Date: 2019-08-15 03:23:38 +0300 (Thu, 15 Aug 2019) $ #$Revision: 217532 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/22/1552225.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1552225 loop_ _publ_author_name 'Zhao, Na' 'Li, Yan' 'Yang, Weiyao' 'Zhuang, Jiabao' 'Li, Yue' 'Li, Nan' _publ_section_title ; Multifunctional pyrazoline based AIEgens: real-time tracking and specific protein “fishing” of lipid droplets ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC03111A _journal_year 2019 _chemical_formula_moiety 'C25 H22 F5 N3' _chemical_formula_sum 'C25 H22 F5 N3' _chemical_formula_weight 459.45 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-02-27 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-20 deposited with the CCDC. 2019-08-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.013(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.5027(9) _cell_length_b 5.9539(3) _cell_length_c 20.2366(9) _cell_measurement_reflns_used 5153 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 71.1180 _cell_measurement_theta_min 3.9230 _cell_volume 2193.55(19) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0356 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -4.00 77.00 1.00 5.25 -- 37.78 -99.00 -60.00 81 2 \w -29.00 55.00 1.00 5.25 -- 37.78 -57.00-120.00 84 3 \w -30.00 65.00 1.00 5.25 -- 37.78 -77.00 150.00 95 4 \w -4.00 77.00 1.00 5.25 -- 37.78 -99.00 30.00 81 5 \w 11.00 105.00 1.00 5.25 -- 37.78 77.00 -90.00 94 6 \w -29.00 55.00 1.00 5.25 -- 37.78 -57.00 30.00 84 7 \w 21.00 105.00 1.00 5.25 -- 37.78 57.00 0.00 84 8 \w 40.00 125.00 1.00 21.00 -- 108.00 -45.00-150.00 85 9 \w 41.00 126.00 1.00 21.00 -- 108.00 -61.00 120.00 85 10 \w 39.00 109.00 1.00 21.00 -- 108.00 -94.00 90.00 70 11 \w 70.00 178.00 1.00 21.00 -- 108.00 15.00 -60.00 108 12 \w 38.00 116.00 1.00 21.00 -- 108.00-111.00-120.00 78 13 \w 37.00 146.00 1.00 21.00 -- 108.00 -15.00 90.00 109 14 \w -34.00 67.00 1.00 5.25 -- 37.78 -19.00 -90.00 101 15 \w 21.00 105.00 1.00 5.25 -- 37.78 57.00 30.00 84 16 \w 11.00 105.00 1.00 5.25 -- 37.78 77.00 150.00 94 17 \w 11.00 105.00 1.00 5.25 -- 37.78 77.00 90.00 94 18 \w 21.00 105.00 1.00 5.25 -- 37.78 57.00-120.00 84 19 \w 21.00 105.00 1.00 5.25 -- 37.78 57.00 90.00 84 20 \w 91.00 176.00 1.00 21.00 -- 108.00 45.00-180.00 85 21 \w 81.00 172.00 1.00 21.00 -- 108.00 77.00 120.00 91 22 \w 81.00 176.00 1.00 21.00 -- 108.00 77.00-150.00 95 23 \w 70.00 178.00 1.00 21.00 -- 108.00 15.00 30.00 108 24 \w 41.00 126.00 1.00 21.00 -- 108.00 -61.00 -30.00 85 25 \w 87.00 178.00 1.00 21.00 -- 108.00 30.00 120.00 91 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0842448000 _diffrn_orient_matrix_UB_12 0.0166173000 _diffrn_orient_matrix_UB_13 0.0238500000 _diffrn_orient_matrix_UB_21 0.0053752000 _diffrn_orient_matrix_UB_22 0.0216306000 _diffrn_orient_matrix_UB_23 0.0775771000 _diffrn_orient_matrix_UB_31 0.0058849000 _diffrn_orient_matrix_UB_32 -0.2572623000 _diffrn_orient_matrix_UB_33 0.0080403000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_unetI/netI 0.0169 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 20846 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.872 _diffrn_reflns_theta_min 3.930 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.961 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50945 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.391 _exptl_crystal_description block _exptl_crystal_F_000 952 _refine_diff_density_max 0.920 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 300 _refine_ls_number_reflns 4257 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0700 _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^)+(0.1611P)^2^+0.4132P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2284 _refine_ls_wR_factor_ref 0.2659 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2869 _reflns_number_total 4257 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL exp_15560 in P21/n #14 exp_15560.res created by SHELXL-2018/3 at 10:56:22 on 27-Feb-2019 REM reset to P21/n #14 CELL 1.54184 19.50267 5.95388 20.23661 90 111.0131 90 ZERR 4 0.00091 0.00031 0.00088 0 0.0051 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F N UNIT 100 88 20 12 L.S. 5 PLAN 5 BOND fmap 2 acta REM REM REM WGHT 0.161100 0.413200 FVAR 4.68624 F1 3 0.188647 0.892909 0.105846 11.00000 0.11647 0.11136 = 0.07677 -0.01461 0.02942 -0.03369 F7 3 0.201869 0.775983 0.235689 11.00000 0.11027 0.15348 = 0.06567 -0.02663 0.02171 -0.02809 F11 3 0.050063 0.234012 0.018504 11.00000 0.09788 0.10196 = 0.07263 -0.01328 0.03454 -0.02129 C3 1 0.120267 0.567252 0.054828 11.00000 0.05535 0.08307 = 0.05895 -0.00260 0.01941 0.00457 N9 4 0.083540 0.496768 -0.069538 11.00000 0.06309 0.10910 = 0.05405 0.00191 0.01666 -0.01138 F13 3 0.141529 0.386213 0.259901 11.00000 0.10877 0.15161 = 0.06069 0.01508 0.03355 0.01173 F19 3 0.064564 0.124726 0.148539 11.00000 0.13027 0.10876 = 0.09588 0.00754 0.05611 -0.01596 C5 1 0.116762 0.626986 -0.016286 11.00000 0.05764 0.08665 = 0.05993 -0.00138 0.01803 0.00126 C4 1 0.164862 0.639437 0.181646 11.00000 0.06853 0.11016 = 0.05766 -0.01168 0.01551 -0.00029 C8 1 0.134240 0.446180 0.194045 11.00000 0.07305 0.11289 = 0.05636 0.00681 0.02360 0.01438 C2 1 0.157501 0.699663 0.113640 11.00000 0.06747 0.08737 = 0.06418 -0.00434 0.02101 -0.00617 C6 1 0.089082 0.374152 0.069819 11.00000 0.06426 0.08701 = 0.06024 -0.00624 0.02201 0.00081 C17 1 0.051137 0.489118 -0.195085 11.00000 0.05377 0.10671 = 0.05323 0.00079 0.01363 0.00152 C12 1 0.095635 0.312763 0.137888 11.00000 0.07629 0.09326 = 0.07134 0.00511 0.03341 0.00545 C18 1 0.201949 0.759635 -0.133425 11.00000 0.07539 0.07251 = 0.05191 0.00433 0.01499 -0.00726 N14 4 0.088968 0.587187 -0.129119 11.00000 0.08520 0.12815 = 0.05367 0.00293 0.02082 -0.03192 C19 1 0.012447 0.292000 -0.199916 11.00000 0.06444 0.10501 = 0.05422 0.00630 0.01625 0.00557 AFIX 43 H19 2 0.011760 0.222859 -0.158949 11.00000 -1.20000 AFIX 0 C27 1 -0.026878 0.296163 -0.328268 11.00000 0.06405 0.13014 = 0.05349 -0.00038 0.01491 0.00942 C23 1 -0.025265 0.196486 -0.265059 11.00000 0.07586 0.10678 = 0.05884 -0.00190 0.01480 0.00112 AFIX 43 H23 2 -0.050287 0.062226 -0.267003 11.00000 -1.20000 AFIX 0 C21 1 0.242390 0.565331 -0.114629 11.00000 0.09465 0.08657 = 0.07027 0.01173 0.02371 0.00239 AFIX 43 H21 2 0.226586 0.450984 -0.092197 11.00000 -1.20000 AFIX 0 C22 1 0.226183 0.927136 -0.166927 11.00000 0.10061 0.08265 = 0.07579 0.00759 0.02778 -0.01619 AFIX 43 H22 2 0.199048 1.058699 -0.180522 11.00000 -1.20000 AFIX 0 C24 1 0.011370 0.493566 -0.322019 11.00000 0.07330 0.14207 = 0.05482 0.01113 0.02141 0.00136 AFIX 43 H24 2 0.010789 0.566299 -0.362886 11.00000 -1.20000 AFIX 0 C15 1 0.133588 0.790633 -0.117025 11.00000 0.08142 0.08451 = 0.06636 0.00873 0.02272 0.00344 AFIX 13 H15 2 0.104398 0.913892 -0.145565 11.00000 -1.20000 AFIX 0 N29 4 -0.063609 0.193868 -0.393548 11.00000 0.11284 0.15620 = 0.05777 -0.01414 0.01717 -0.01509 C9BA 1 0.147920 0.833892 -0.037553 11.00000 0.10013 0.09344 = 0.07362 -0.00273 0.03649 -0.00525 AFIX 23 H9BA 2 0.200028 0.848623 -0.010535 11.00000 -1.20000 H9BB 2 0.122783 0.968151 -0.031211 11.00000 -1.20000 AFIX 0 C20 1 0.050598 0.587443 -0.257152 11.00000 0.07571 0.12948 = 0.06135 0.00956 0.02017 -0.01315 AFIX 43 H20 2 0.077078 0.718808 -0.255121 11.00000 -1.20000 AFIX 0 C26 1 0.290317 0.901278 -0.180455 11.00000 0.10269 0.12342 = 0.09274 -0.00294 0.04201 -0.03695 AFIX 43 H26 2 0.306680 1.015685 -0.202410 11.00000 -1.20000 AFIX 0 C2CA 1 -0.067806 0.297587 -0.458343 11.00000 0.19803 0.21442 = 0.05724 -0.00355 0.01228 -0.04889 AFIX 23 H2CA 2 -0.022131 0.376245 -0.451136 11.00000 -1.20000 H2CB 2 -0.073178 0.181861 -0.493590 11.00000 -1.20000 AFIX 0 C28 1 0.329784 0.705410 -0.161259 11.00000 0.08009 0.15484 = 0.08289 -0.01930 0.03036 -0.01879 AFIX 43 H28 2 0.372792 0.687524 -0.170630 11.00000 -1.20000 AFIX 0 C25 1 0.306683 0.537487 -0.128731 11.00000 0.08568 0.11823 = 0.08456 -0.00658 0.01706 0.01371 AFIX 43 H25 2 0.333592 0.405223 -0.116017 11.00000 -1.20000 AFIX 0 C32 1 -0.184407 0.081802 -0.395870 11.00000 0.14885 0.58462 = 0.11743 -0.07407 0.05187 -0.15522 AFIX 137 H32A 2 -0.176929 0.139859 -0.349543 11.00000 -1.50000 H32B 2 -0.215652 -0.047891 -0.404593 11.00000 -1.50000 H32C 2 -0.207111 0.194780 -0.430703 11.00000 -1.50000 AFIX 0 C6CA 1 -0.111647 0.017075 -0.400205 11.00000 0.22791 0.18007 = 0.06803 -0.03101 0.02274 -0.07171 AFIX 23 H6CA 2 -0.088297 -0.091639 -0.363270 11.00000 -1.20000 H6CB 2 -0.120435 -0.056092 -0.445333 11.00000 -1.20000 AFIX 0 C1 1 -0.124853 0.445930 -0.483665 11.00000 0.56917 0.26749 = 0.19126 0.06737 -0.05368 -0.02933 AFIX 137 H1A 2 -0.151963 0.449467 -0.452357 11.00000 -1.50000 H1B 2 -0.156676 0.399359 -0.529919 11.00000 -1.50000 H1C 2 -0.105952 0.593060 -0.486487 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_15560 in P21/n #14 REM wR2 = 0.2659, GooF = S = 1.054, Restrained GooF = 1.054 for all data REM R1 = 0.0700 for 2869 Fo > 4sig(Fo) and 0.0925 for all 4257 data REM 300 parameters refined using 0 restraints END WGHT 0.1611 0.4132 REM Highest difference peak 0.920, deepest hole -0.235, 1-sigma level 0.053 Q1 1 -0.0198 0.1873 -0.4903 11.00000 0.05 0.92 Q2 1 -0.0827 0.3161 -0.3828 11.00000 0.05 0.13 Q3 1 0.0814 0.3738 0.1001 11.00000 0.05 0.13 Q4 1 0.0030 0.5829 -0.2963 11.00000 0.05 0.13 Q5 1 0.2411 0.9356 -0.1236 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0700 for 2869 Fo > 4sig(Fo) and 0.0925 for all 22534 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.92, deepest hole -0.23 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0925 REM R1_gt = 0.0700 REM wR_ref = 0.2659 REM GOOF = 1.054 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 22534 REM Reflections_gt = 2869 REM Parameters = n/a REM Hole = -0.23 REM Peak = 0.92 REM Flack = n/a ; _cod_data_source_file c9sc03111a2.cif _cod_data_source_block exp_15560 _cod_original_cell_volume 2193.54(19) _cod_database_code 1552225 _shelx_shelxl_version_number 2018/3 _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. ; _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C15(H15) 2.b Secondary CH2 refined with riding coordinates: C9BA(H9BA,H9BB), C2CA(H2CA,H2CB), C6CA(H6CA,H6CB) 2.c Aromatic/amide H refined with riding coordinates: C19(H19), C23(H23), C21(H21), C22(H22), C24(H24), C20(H20), C26(H26), C28(H28), C25(H25) 2.d Idealised Me refined as rotating group: C32(H32A,H32B,H32C), C1(H1A,H1B,H1C) ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.327 _oxdiff_exptl_absorpt_empirical_full_min 0.544 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 F1 F 0.18865(12) 0.8929(4) 0.10585(10) 0.1030(7) Uani 1 1 d . F7 F 0.20187(12) 0.7760(4) 0.23569(9) 0.1125(8) Uani 1 1 d . F11 F 0.05006(10) 0.2340(3) 0.01850(9) 0.0897(6) Uani 1 1 d . C3 C 0.12027(12) 0.5673(5) 0.05483(13) 0.0661(7) Uani 1 1 d . N9 N 0.08354(12) 0.4968(5) -0.06954(11) 0.0766(7) Uani 1 1 d . F13 F 0.14153(11) 0.3862(4) 0.25990(9) 0.1062(7) Uani 1 1 d . F19 F 0.06456(12) 0.1247(4) 0.14854(11) 0.1074(7) Uani 1 1 d . C5 C 0.11676(13) 0.6270(5) -0.01629(13) 0.0689(7) Uani 1 1 d . C4 C 0.16486(15) 0.6394(6) 0.18165(14) 0.0807(8) Uani 1 1 d . C8 C 0.13424(15) 0.4462(6) 0.19404(14) 0.0807(9) Uani 1 1 d . C2 C 0.15750(15) 0.6997(5) 0.11364(14) 0.0737(7) Uani 1 1 d . C6 C 0.08908(14) 0.3742(5) 0.06982(13) 0.0706(7) Uani 1 1 d . C17 C 0.05114(13) 0.4891(6) -0.19509(13) 0.0728(8) Uani 1 1 d . C12 C 0.09563(16) 0.3128(6) 0.13789(15) 0.0784(8) Uani 1 1 d . C18 C 0.20195(14) 0.7596(5) -0.13343(12) 0.0688(7) Uani 1 1 d . N14 N 0.08897(14) 0.5872(6) -0.12912(12) 0.0901(8) Uani 1 1 d . C19 C 0.01245(14) 0.2920(6) -0.19992(14) 0.0759(8) Uani 1 1 d . H19 H 0.011760 0.222859 -0.158949 0.091 Uiso 1 1 calc R C27 C -0.02688(15) 0.2962(7) -0.32827(14) 0.0843(9) Uani 1 1 d . C23 C -0.02526(16) 0.1965(6) -0.26506(15) 0.0831(8) Uani 1 1 d . H23 H -0.050287 0.062226 -0.267003 0.100 Uiso 1 1 calc R C21 C 0.24239(18) 0.5653(6) -0.11463(16) 0.0854(9) Uani 1 1 d . H21 H 0.226586 0.450984 -0.092197 0.103 Uiso 1 1 calc R C22 C 0.22618(18) 0.9271(6) -0.16693(16) 0.0874(9) Uani 1 1 d . H22 H 0.199048 1.058699 -0.180522 0.105 Uiso 1 1 calc R C24 C 0.01137(16) 0.4936(7) -0.32202(15) 0.0905(10) Uani 1 1 d . H24 H 0.010789 0.566299 -0.362886 0.109 Uiso 1 1 calc R C15 C 0.13359(17) 0.7906(5) -0.11703(15) 0.0785(8) Uani 1 1 d . H15 H 0.104398 0.913892 -0.145565 0.094 Uiso 1 1 calc R N29 N -0.06361(19) 0.1939(7) -0.39355(14) 0.1126(11) Uani 1 1 d . C9BA C 0.14792(19) 0.8339(6) -0.03755(17) 0.0876(9) Uani 1 1 d . H9BA H 0.200028 0.848623 -0.010535 0.105 Uiso 1 1 calc R H9BB H 0.122783 0.968151 -0.031211 0.105 Uiso 1 1 calc R C20 C 0.05060(16) 0.5874(7) -0.25715(15) 0.0901(10) Uani 1 1 d . H20 H 0.077078 0.718808 -0.255121 0.108 Uiso 1 1 calc R C26 C 0.2903(2) 0.9013(8) -0.1805(2) 0.1044(12) Uani 1 1 d . H26 H 0.306680 1.015685 -0.202410 0.125 Uiso 1 1 calc R C2CA C -0.0678(4) 0.2976(13) -0.4583(2) 0.166(3) Uani 1 1 d . H2CA H -0.022131 0.376245 -0.451136 0.199 Uiso 1 1 calc R H2CB H -0.073178 0.181861 -0.493590 0.199 Uiso 1 1 calc R C28 C 0.3298(2) 0.7054(9) -0.1613(2) 0.1056(13) Uani 1 1 d . H28 H 0.372792 0.687524 -0.170630 0.127 Uiso 1 1 calc R C25 C 0.30668(19) 0.5375(8) -0.12873(19) 0.0999(11) Uani 1 1 d . H25 H 0.333592 0.405223 -0.116017 0.120 Uiso 1 1 calc R C32 C -0.1844(4) 0.082(2) -0.3959(3) 0.282(7) Uani 1 1 d . H32A H -0.176929 0.139859 -0.349543 0.424 Uiso 1 1 calc GR H32B H -0.215652 -0.047891 -0.404593 0.424 Uiso 1 1 calc GR H32C H -0.207111 0.194780 -0.430703 0.424 Uiso 1 1 calc GR C6CA C -0.1116(4) 0.0171(11) -0.4002(2) 0.167(3) Uani 1 1 d . H6CA H -0.088297 -0.091639 -0.363270 0.200 Uiso 1 1 calc R H6CB H -0.120435 -0.056092 -0.445333 0.200 Uiso 1 1 calc R C1 C -0.1249(9) 0.446(2) -0.4837(6) 0.395(11) Uani 1 1 d . H1A H -0.151963 0.449467 -0.452357 0.592 Uiso 1 1 calc GR H1B H -0.156676 0.399359 -0.529919 0.592 Uiso 1 1 calc GR H1C H -0.105952 0.593060 -0.486487 0.592 Uiso 1 1 calc GR 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 0.1165(14) 0.1114(15) 0.0768(11) -0.0146(10) 0.0294(10) -0.0337(12) F7 0.1103(14) 0.153(2) 0.0657(11) -0.0266(11) 0.0217(10) -0.0281(13) F11 0.0979(11) 0.1020(14) 0.0726(10) -0.0133(9) 0.0345(9) -0.0213(10) C3 0.0553(12) 0.0831(18) 0.0590(13) -0.0026(12) 0.0194(10) 0.0046(11) N9 0.0631(11) 0.1091(19) 0.0541(12) 0.0019(11) 0.0167(9) -0.0114(12) F13 0.1088(13) 0.152(2) 0.0607(9) 0.0151(10) 0.0336(9) 0.0117(13) F19 0.1303(16) 0.1088(16) 0.0959(13) 0.0075(11) 0.0561(12) -0.0160(12) C5 0.0576(12) 0.0867(19) 0.0599(13) -0.0014(12) 0.0180(10) 0.0013(12) C4 0.0685(15) 0.110(2) 0.0577(14) -0.0117(14) 0.0155(11) -0.0003(15) C8 0.0730(15) 0.113(3) 0.0564(14) 0.0068(14) 0.0236(12) 0.0144(16) C2 0.0675(14) 0.087(2) 0.0642(15) -0.0043(13) 0.0210(12) -0.0062(13) C6 0.0643(13) 0.0870(19) 0.0602(14) -0.0062(12) 0.0220(11) 0.0008(13) C17 0.0538(12) 0.107(2) 0.0532(13) 0.0008(13) 0.0136(10) 0.0015(13) C12 0.0763(16) 0.093(2) 0.0713(17) 0.0051(15) 0.0334(13) 0.0055(15) C18 0.0754(15) 0.0725(17) 0.0519(12) 0.0043(11) 0.0150(11) -0.0073(12) N14 0.0852(15) 0.128(2) 0.0537(12) 0.0029(12) 0.0208(10) -0.0319(15) C19 0.0644(13) 0.105(2) 0.0542(13) 0.0063(13) 0.0163(11) 0.0056(15) C27 0.0641(14) 0.130(3) 0.0535(14) -0.0004(15) 0.0149(11) 0.0094(17) C23 0.0759(15) 0.107(2) 0.0588(15) -0.0019(14) 0.0148(12) 0.0011(16) C21 0.0946(19) 0.087(2) 0.0703(16) 0.0117(14) 0.0237(14) 0.0024(16) C22 0.101(2) 0.083(2) 0.0758(17) 0.0076(15) 0.0278(15) -0.0162(16) C24 0.0733(16) 0.142(3) 0.0548(14) 0.0111(17) 0.0214(12) 0.0014(19) C15 0.0814(16) 0.085(2) 0.0664(15) 0.0087(13) 0.0227(13) 0.0034(15) N29 0.113(2) 0.156(3) 0.0578(15) -0.0141(16) 0.0172(14) -0.015(2) C9BA 0.100(2) 0.093(2) 0.0736(18) -0.0027(15) 0.0365(15) -0.0053(17) C20 0.0757(16) 0.129(3) 0.0614(15) 0.0096(16) 0.0202(12) -0.0132(17) C26 0.103(2) 0.123(3) 0.093(2) -0.003(2) 0.0420(19) -0.037(2) C2CA 0.198(6) 0.214(7) 0.057(2) -0.004(3) 0.012(3) -0.049(5) C28 0.0801(19) 0.155(4) 0.083(2) -0.019(2) 0.0304(16) -0.019(2) C25 0.086(2) 0.118(3) 0.085(2) -0.007(2) 0.0171(16) 0.014(2) C32 0.149(5) 0.58(2) 0.117(5) -0.074(8) 0.052(4) -0.155(9) C6CA 0.228(6) 0.180(5) 0.068(2) -0.031(3) 0.023(3) -0.072(5) C1 0.57(2) 0.267(13) 0.191(10) 0.067(10) -0.054(13) -0.029(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C3 C5 122.0(3) C6 C3 C5 123.3(2) C6 C3 C2 114.7(2) C5 N9 N14 109.0(3) C3 C5 C9BA 126.9(2) N9 C5 C3 120.4(3) N9 C5 C9BA 112.6(2) F7 C4 C8 120.3(3) F7 C4 C2 119.2(3) C8 C4 C2 120.6(3) F13 C8 C4 120.9(3) F13 C8 C12 120.2(3) C4 C8 C12 119.0(3) F1 C2 C3 120.4(3) F1 C2 C4 116.9(3) C4 C2 C3 122.7(3) F11 C6 C3 121.4(2) F11 C6 C12 115.6(3) C3 C6 C12 123.1(3) C19 C17 N14 120.7(3) C19 C17 C20 118.0(3) C20 C17 N14 121.3(3) F19 C12 C8 120.1(3) F19 C12 C6 119.9(3) C8 C12 C6 119.9(3) C21 C18 C22 118.7(3) C21 C18 C15 120.7(3) C22 C18 C15 120.6(3) N9 N14 C17 119.9(3) N9 N14 C15 114.3(2) C17 N14 C15 125.8(2) C17 C19 C23 120.6(3) C24 C27 C23 116.4(3) C24 C27 N29 122.5(3) N29 C27 C23 121.0(4) C19 C23 C27 121.8(3) C18 C21 C25 120.9(3) C18 C22 C26 120.7(4) C27 C24 C20 122.2(3) C18 C15 C9BA 114.0(2) N14 C15 C18 112.7(3) N14 C15 C9BA 100.7(2) C27 N29 C2CA 121.5(4) C6CA N29 C27 121.6(3) C6CA N29 C2CA 115.3(4) C5 C9BA C15 102.7(2) C24 C20 C17 120.9(3) C28 C26 C22 119.6(4) C1 C2CA N29 113.3(8) C25 C28 C26 120.8(3) C28 C25 C21 119.4(4) N29 C6CA C32 114.8(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C2 1.337(4) F7 C4 1.346(3) F11 C6 1.337(3) C3 C5 1.460(4) C3 C2 1.395(4) C3 C6 1.384(4) N9 C5 1.297(4) N9 N14 1.359(3) F13 C8 1.337(3) F19 C12 1.327(4) C5 C9BA 1.503(4) C4 C8 1.361(5) C4 C2 1.379(4) C8 C12 1.370(4) C6 C12 1.386(4) C17 N14 1.400(4) C17 C19 1.380(4) C17 C20 1.382(4) C18 C21 1.375(4) C18 C22 1.381(4) C18 C15 1.496(4) N14 C15 1.460(4) C19 C23 1.381(4) C27 C23 1.400(5) C27 C24 1.373(5) C27 N29 1.397(4) C21 C25 1.392(5) C22 C26 1.382(5) C24 C20 1.379(4) C15 C9BA 1.552(4) N29 C2CA 1.425(6) N29 C6CA 1.383(7) C26 C28 1.374(6) C2CA C1 1.368(13) C28 C25 1.360(6) C32 C6CA 1.503(9)