#------------------------------------------------------------------------------ #$Date: 2023-11-24 02:38:02 +0200 (Fri, 24 Nov 2023) $ #$Revision: 287767 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247788.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_7247788 loop_ _publ_author_name 'Lamba, Manisha' 'Singh, Prasoon Raj' 'Bhatt, Shubham' 'Goswami, Avijit' _publ_section_title ; Metal- and Additive-Free TfOH Catalyzed Chemoselective O- and S-Trifluoroethylation of Oxindoles, Isoindolines and Thioxindoles ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03702A _journal_year 2023 _chemical_formula_moiety 'C28 H26 Br F3 N O' _chemical_formula_sum 'C28 H26 Br F3 N O' _chemical_formula_weight 529.41 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-08-04 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-08-04 deposited with the CCDC. 2023-11-23 downloaded from the CCDC. ; _cell_angle_alpha 75.9800(10) _cell_angle_beta 78.6930(10) _cell_angle_gamma 81.3380(10) _cell_formula_units_Z 2 _cell_length_a 7.9716(2) _cell_length_b 10.9315(3) _cell_length_c 15.7731(4) _cell_measurement_reflns_used 9952 _cell_measurement_temperature 298 _cell_measurement_theta_max 28.432 _cell_measurement_theta_min 2.622 _cell_volume 1299.96(6) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 298.00 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX2 area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_unetI/netI 0.0362 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 35476 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.452 _diffrn_reflns_theta_min 1.932 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 1.622 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.4234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1367 before and 0.0822 after correction. The Ratio of minimum to maximum transmission is 0.5678. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.353 _exptl_crystal_description block _exptl_crystal_F_000 542 _exptl_crystal_size_max 0.215 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.125 _refine_diff_density_max 2.000 _refine_diff_density_min -1.424 _refine_diff_density_rms 0.068 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 313 _refine_ls_number_reflns 6457 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0639 _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^)+(0.0707P)^2^+1.7545P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1626 _refine_ls_wR_factor_ref 0.1725 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5278 _reflns_number_total 6457 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03702a2.cif _cod_data_source_block agml_1127_0m _cod_database_code 7247788 _shelx_shelxl_version_number 2019/1 _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. ; _shelx_estimated_absorpt_t_max 0.823 _shelx_estimated_absorpt_t_min 0.722 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C27(H27), C15(H15), C8(H8), C24(H24), C21(H21), C2(H2), C11(H11) 2.b Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C23(H23A,H23B, H23C), C20(H20A,H20B,H20C), C26(H26A,H26B,H26C) ; _shelx_res_file ; TITL agml_1127_0m_a.res in P-1 agml_1127_0m.res created by SHELXL-2019/1 at 17:18:57 on 04-Aug-2023 REM Old TITL agml_1127_0m_a.res in P-1 REM SHELXT solution in P-1: R1 0.311, Rweak 0.043, Alpha 0.075 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C30 Br N O2 CELL 0.71073 7.9716 10.9315 15.7731 75.98 78.693 81.338 ZERR 2 0.0002 0.0003 0.0004 0.001 0.001 0.001 LATT 1 SFAC C H Br F N O UNIT 56 52 2 6 2 2 L.S. 4 PLAN 5 0 0 SIZE 0.212 0.215 0.125 TEMP 24.85 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.070700 1.754500 FVAR 1.30539 BR1 3 0.190442 0.046794 0.606876 11.00000 0.11665 0.05066 = 0.04301 0.00677 -0.02277 -0.03442 O1 6 0.305908 0.498274 0.147753 11.00000 0.10240 0.07149 = 0.04708 0.02096 -0.03513 -0.05436 N1 5 0.360087 0.463001 0.289511 11.00000 0.06367 0.04265 = 0.04656 0.00599 -0.02154 -0.02812 AFIX 43 H1 2 0.411403 0.530284 0.278596 11.00000 -1.20000 AFIX 0 C28 1 0.333750 0.378486 0.369691 11.00000 0.04702 0.03581 = 0.04415 0.00040 -0.01624 -0.01452 F3 4 0.353336 0.632746 -0.018988 11.00000 0.12486 0.15077 = 0.07596 0.04480 -0.02368 -0.08481 C4 1 0.219832 0.310721 0.267194 11.00000 0.04152 0.03955 = 0.03862 0.00021 -0.01323 -0.01410 C3 1 0.290550 0.421807 0.229727 11.00000 0.05380 0.04459 = 0.04126 0.00577 -0.01820 -0.02059 C14 1 0.247572 0.281878 0.357704 11.00000 0.04666 0.03496 = 0.04064 -0.00121 -0.01582 -0.01235 C18 1 0.367210 0.281268 0.612570 11.00000 0.05749 0.03800 = 0.04084 -0.00686 -0.01634 -0.00981 C5 1 0.138026 0.229651 0.227578 11.00000 0.04109 0.03549 = 0.03465 0.00149 -0.01223 -0.01391 C17 1 0.332396 0.281136 0.522520 11.00000 0.05644 0.03901 = 0.04149 -0.00648 -0.01802 -0.00886 C6 1 -0.042887 0.234748 0.239818 11.00000 0.03839 0.04004 = 0.03886 -0.00013 -0.00861 -0.00943 C27 1 0.375244 0.379504 0.450712 11.00000 0.05802 0.03778 = 0.04775 -0.00507 -0.02062 -0.01579 AFIX 43 H27 2 0.430871 0.444984 0.456895 11.00000 -1.20000 AFIX 0 C15 1 0.205173 0.182351 0.429488 11.00000 0.06667 0.03595 = 0.04240 -0.00093 -0.01816 -0.02003 AFIX 43 H15 2 0.148696 0.117126 0.423596 11.00000 -1.20000 AFIX 0 C8 1 -0.115870 0.156287 0.203739 11.00000 0.03948 0.05078 = 0.04618 -0.00015 -0.01212 -0.01887 AFIX 43 H8 2 -0.235168 0.161272 0.211157 11.00000 -1.20000 AFIX 0 C25 1 0.235617 0.325439 0.673520 11.00000 0.06462 0.05055 = 0.05898 -0.02035 -0.01318 -0.01093 C24 1 0.266489 0.317629 0.758808 11.00000 0.08486 0.05559 = 0.05236 -0.02315 0.00060 -0.02297 AFIX 43 H24 2 0.178764 0.347410 0.799569 11.00000 -1.20000 AFIX 0 C9 1 -0.018515 0.071050 0.157239 11.00000 0.05484 0.04805 = 0.04511 -0.00486 -0.01164 -0.02251 C16 1 0.249508 0.183541 0.509492 11.00000 0.06884 0.03803 = 0.03867 0.00062 -0.01496 -0.01613 C21 1 0.551402 0.228104 0.722867 11.00000 0.07586 0.05223 = 0.05452 -0.00023 -0.03301 -0.01451 AFIX 43 H21 2 0.658352 0.196332 0.738962 11.00000 -1.20000 AFIX 0 C19 1 0.527704 0.234194 0.636597 11.00000 0.06223 0.05020 = 0.04850 -0.00730 -0.02035 -0.00807 C22 1 0.421546 0.267616 0.784698 11.00000 0.09999 0.04517 = 0.04416 -0.00415 -0.02124 -0.03290 F2 4 0.150740 0.565914 -0.051207 11.00000 0.23008 0.19422 = 0.09949 0.07470 -0.11053 -0.13725 C2 1 0.217810 0.474369 0.087093 11.00000 0.09006 0.06566 = 0.05192 0.01818 -0.03698 -0.04074 AFIX 43 H2 2 0.172505 0.399354 0.090661 11.00000 -1.20000 AFIX 0 C12 1 0.238227 0.143271 0.180934 11.00000 0.03852 0.04567 = 0.05620 -0.00688 -0.00870 -0.01085 C11 1 0.158373 0.066345 0.145921 11.00000 0.05355 0.04949 = 0.05928 -0.01882 -0.00255 -0.01211 AFIX 43 H11 2 0.226158 0.010217 0.114011 11.00000 -1.20000 AFIX 0 C7 1 -0.157834 0.323142 0.292310 11.00000 0.04885 0.06903 = 0.08167 -0.02923 -0.00208 -0.00514 AFIX 137 H7A 2 -0.131205 0.304762 0.351176 11.00000 -1.50000 H7B 2 -0.275998 0.311517 0.295258 11.00000 -1.50000 H7C 2 -0.139344 0.409316 0.263852 11.00000 -1.50000 AFIX 0 C13 1 0.432789 0.129151 0.169528 11.00000 0.04118 0.07419 = 0.12159 -0.03366 -0.00648 -0.00875 AFIX 137 H13A 2 0.473194 0.211366 0.149001 11.00000 -1.50000 H13B 2 0.480086 0.078136 0.127011 11.00000 -1.50000 H13C 2 0.468418 0.089000 0.225341 11.00000 -1.50000 AFIX 0 C10 1 -0.104542 -0.014651 0.121670 11.00000 0.08229 0.08013 = 0.08698 -0.03384 -0.01468 -0.03658 AFIX 137 H10A 2 -0.187804 -0.056213 0.168054 11.00000 -1.50000 H10B 2 -0.019661 -0.077113 0.100214 11.00000 -1.50000 H10C 2 -0.161076 0.034668 0.074036 11.00000 -1.50000 AFIX 0 C23 1 0.445201 0.253839 0.879771 11.00000 0.15778 0.08408 = 0.04777 -0.00649 -0.03286 -0.04917 AFIX 137 H23A 2 0.426866 0.335911 0.893981 11.00000 -1.50000 H23B 2 0.559922 0.216203 0.886698 11.00000 -1.50000 H23C 2 0.363790 0.200682 0.918817 11.00000 -1.50000 AFIX 0 C1 1 0.208881 0.590465 0.015256 11.00000 0.07782 0.08123 = 0.06339 0.02665 -0.03288 -0.03430 C20 1 0.673182 0.186107 0.571903 11.00000 0.07881 0.12261 = 0.07499 -0.03108 -0.02424 0.01775 AFIX 137 H20A 2 0.635072 0.124096 0.548167 11.00000 -1.50000 H20B 2 0.768367 0.148057 0.601817 11.00000 -1.50000 H20C 2 0.708707 0.255562 0.524548 11.00000 -1.50000 AFIX 0 C26 1 0.059286 0.376211 0.649614 11.00000 0.06954 0.10165 = 0.10872 -0.05544 -0.02322 0.01153 AFIX 137 H26A 2 0.069280 0.448747 0.601110 11.00000 -1.50000 H26B 2 -0.015240 0.400424 0.699896 11.00000 -1.50000 H26C 2 0.012139 0.311618 0.632695 11.00000 -1.50000 AFIX 0 F1 4 0.111573 0.680146 0.038377 11.00000 0.24117 0.13508 = 0.17588 0.06892 0.05439 0.10242 HKLF 4 REM agml_1127_0m_a.res in P-1 REM wR2 = 0.1725, GooF = S = 1.030, Restrained GooF = 1.030 for all data REM R1 = 0.0639 for 5278 Fo > 4sig(Fo) and 0.0766 for all 6457 data REM 313 parameters refined using 0 restraints END WGHT 0.0707 1.7545 REM Highest difference peak 2.000, deepest hole -1.424, 1-sigma level 0.068 Q1 1 0.3078 0.0239 0.5929 11.00000 0.05 2.00 Q2 1 0.2446 0.7043 0.0198 11.00000 0.05 0.59 Q3 1 0.0634 0.6281 -0.0077 11.00000 0.05 0.45 Q4 1 0.0761 0.4733 0.1210 11.00000 0.05 0.40 Q5 1 0.3062 0.5749 -0.0537 11.00000 0.05 0.31 ; _shelx_res_checksum 28753 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 Br1 Br 0.19044(6) 0.04679(3) 0.60688(2) 0.06905(18) Uani 1 1 d . . . . . O1 O 0.3059(4) 0.4983(3) 0.14775(17) 0.0716(8) Uani 1 1 d . . . . . N1 N 0.3601(4) 0.4630(2) 0.28951(18) 0.0496(6) Uani 1 1 d . . . . . H1 H 0.411403 0.530284 0.278596 0.060 Uiso 1 1 calc R U . . . C28 C 0.3337(4) 0.3785(3) 0.3697(2) 0.0416(6) Uani 1 1 d . . . . . F3 F 0.3533(5) 0.6327(4) -0.0190(2) 0.1209(13) Uani 1 1 d . . . . . C4 C 0.2198(4) 0.3107(3) 0.26719(18) 0.0395(6) Uani 1 1 d . . . . . C3 C 0.2906(4) 0.4218(3) 0.2297(2) 0.0461(7) Uani 1 1 d . . . . . C14 C 0.2476(4) 0.2819(3) 0.35770(19) 0.0400(6) Uani 1 1 d . . . . . C18 C 0.3672(4) 0.2813(3) 0.6126(2) 0.0441(6) Uani 1 1 d . . . . . C5 C 0.1380(3) 0.2297(3) 0.22758(17) 0.0368(5) Uani 1 1 d . . . . . C17 C 0.3324(4) 0.2811(3) 0.5225(2) 0.0443(6) Uani 1 1 d . . . . . C6 C -0.0429(4) 0.2347(3) 0.23982(19) 0.0397(6) Uani 1 1 d . . . . . C27 C 0.3752(4) 0.3795(3) 0.4507(2) 0.0458(7) Uani 1 1 d . . . . . H27 H 0.430871 0.444984 0.456895 0.055 Uiso 1 1 calc R U . . . C15 C 0.2052(4) 0.1824(3) 0.4295(2) 0.0469(7) Uani 1 1 d . . . . . H15 H 0.148696 0.117126 0.423596 0.056 Uiso 1 1 calc R U . . . C8 C -0.1159(4) 0.1563(3) 0.2037(2) 0.0451(7) Uani 1 1 d . . . . . H8 H -0.235168 0.161272 0.211157 0.054 Uiso 1 1 calc R U . . . C25 C 0.2356(5) 0.3254(3) 0.6735(2) 0.0557(8) Uani 1 1 d . . . . . C24 C 0.2665(6) 0.3176(4) 0.7588(3) 0.0623(9) Uani 1 1 d . . . . . H24 H 0.178764 0.347410 0.799569 0.075 Uiso 1 1 calc R U . . . C9 C -0.0185(4) 0.0710(3) 0.1572(2) 0.0480(7) Uani 1 1 d . . . . . C16 C 0.2495(5) 0.1835(3) 0.5095(2) 0.0481(7) Uani 1 1 d . . . . . C21 C 0.5514(5) 0.2281(3) 0.7229(2) 0.0590(9) Uani 1 1 d . . . . . H21 H 0.658352 0.196332 0.738962 0.071 Uiso 1 1 calc R U . . . C19 C 0.5277(5) 0.2342(3) 0.6366(2) 0.0525(7) Uani 1 1 d . . . . . C22 C 0.4215(6) 0.2676(3) 0.7847(2) 0.0601(9) Uani 1 1 d . . . . . F2 F 0.1507(7) 0.5659(5) -0.0512(3) 0.169(2) Uani 1 1 d . . . . . C2 C 0.2178(6) 0.4744(4) 0.0871(2) 0.0677(11) Uani 1 1 d . . . . . H2 H 0.172505 0.399354 0.090661 0.081 Uiso 1 1 calc R U . . . C12 C 0.2382(4) 0.1433(3) 0.1809(2) 0.0468(7) Uani 1 1 d . . . . . C11 C 0.1584(4) 0.0663(3) 0.1459(2) 0.0532(8) Uani 1 1 d . . . . . H11 H 0.226158 0.010217 0.114011 0.064 Uiso 1 1 calc R U . . . C7 C -0.1578(5) 0.3231(4) 0.2923(3) 0.0657(10) Uani 1 1 d . . . . . H7A H -0.131205 0.304762 0.351176 0.098 Uiso 1 1 calc R U . . . H7B H -0.275998 0.311517 0.295258 0.098 Uiso 1 1 calc R U . . . H7C H -0.139344 0.409316 0.263852 0.098 Uiso 1 1 calc R U . . . C13 C 0.4328(5) 0.1292(5) 0.1695(4) 0.0776(13) Uani 1 1 d . . . . . H13A H 0.473194 0.211366 0.149001 0.116 Uiso 1 1 calc R U . . . H13B H 0.480086 0.078136 0.127011 0.116 Uiso 1 1 calc R U . . . H13C H 0.468418 0.089000 0.225341 0.116 Uiso 1 1 calc R U . . . C10 C -0.1045(6) -0.0147(5) 0.1217(3) 0.0774(12) Uani 1 1 d . . . . . H10A H -0.187804 -0.056213 0.168054 0.116 Uiso 1 1 calc R U . . . H10B H -0.019661 -0.077113 0.100214 0.116 Uiso 1 1 calc R U . . . H10C H -0.161076 0.034668 0.074036 0.116 Uiso 1 1 calc R U . . . C23 C 0.4452(9) 0.2538(5) 0.8798(3) 0.0919(16) Uani 1 1 d . . . . . H23A H 0.426866 0.335911 0.893981 0.138 Uiso 1 1 calc R U . . . H23B H 0.559922 0.216203 0.886698 0.138 Uiso 1 1 calc R U . . . H23C H 0.363790 0.200682 0.918817 0.138 Uiso 1 1 calc R U . . . C1 C 0.2089(6) 0.5905(5) 0.0153(3) 0.0759(13) Uani 1 1 d . . . . . C20 C 0.6732(7) 0.1861(6) 0.5719(3) 0.0919(16) Uani 1 1 d . . . . . H20A H 0.635072 0.124096 0.548167 0.138 Uiso 1 1 calc R U . . . H20B H 0.768367 0.148057 0.601817 0.138 Uiso 1 1 calc R U . . . H20C H 0.708707 0.255562 0.524548 0.138 Uiso 1 1 calc R U . . . C26 C 0.0593(6) 0.3762(6) 0.6496(4) 0.0887(15) Uani 1 1 d . . . . . H26A H 0.069280 0.448747 0.601110 0.133 Uiso 1 1 calc R U . . . H26B H -0.015240 0.400424 0.699896 0.133 Uiso 1 1 calc R U . . . H26C H 0.012139 0.311618 0.632695 0.133 Uiso 1 1 calc R U . . . F1 F 0.1116(9) 0.6801(5) 0.0384(4) 0.228(4) 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 Br1 0.1167(4) 0.0507(2) 0.0430(2) 0.00677(14) -0.02277(19) -0.0344(2) O1 0.102(2) 0.0715(17) 0.0471(13) 0.0210(12) -0.0351(13) -0.0544(15) N1 0.0637(16) 0.0426(13) 0.0466(14) 0.0060(11) -0.0215(12) -0.0281(12) C28 0.0470(15) 0.0358(13) 0.0442(15) 0.0004(11) -0.0162(12) -0.0145(11) F3 0.125(2) 0.151(3) 0.0760(18) 0.0448(19) -0.0237(17) -0.085(2) C4 0.0415(14) 0.0396(14) 0.0386(13) 0.0002(11) -0.0132(11) -0.0141(11) C3 0.0538(17) 0.0446(15) 0.0413(15) 0.0058(12) -0.0182(13) -0.0206(13) C14 0.0467(15) 0.0350(13) 0.0406(14) -0.0012(11) -0.0158(11) -0.0123(11) C18 0.0575(17) 0.0380(14) 0.0408(14) -0.0069(11) -0.0163(13) -0.0098(12) C5 0.0411(13) 0.0355(13) 0.0347(12) 0.0015(10) -0.0122(10) -0.0139(10) C17 0.0564(17) 0.0390(14) 0.0415(14) -0.0065(11) -0.0180(13) -0.0089(12) C6 0.0384(13) 0.0400(14) 0.0389(13) -0.0001(11) -0.0086(11) -0.0094(11) C27 0.0580(17) 0.0378(14) 0.0477(16) -0.0051(12) -0.0206(13) -0.0158(12) C15 0.0667(19) 0.0360(14) 0.0424(15) -0.0009(11) -0.0182(13) -0.0200(13) C8 0.0395(14) 0.0508(16) 0.0462(15) -0.0002(13) -0.0121(12) -0.0189(12) C25 0.065(2) 0.0506(18) 0.059(2) -0.0204(15) -0.0132(16) -0.0109(15) C24 0.085(3) 0.056(2) 0.0524(19) -0.0231(16) 0.0006(18) -0.0230(18) C9 0.0548(17) 0.0481(16) 0.0451(15) -0.0049(13) -0.0116(13) -0.0225(14) C16 0.069(2) 0.0380(14) 0.0387(14) 0.0006(11) -0.0150(13) -0.0161(13) C21 0.076(2) 0.0522(19) 0.0545(19) -0.0002(15) -0.0330(18) -0.0145(17) C19 0.0622(19) 0.0502(17) 0.0485(17) -0.0073(14) -0.0203(15) -0.0081(15) C22 0.100(3) 0.0452(17) 0.0442(17) -0.0041(13) -0.0212(18) -0.0329(18) F2 0.230(5) 0.194(4) 0.099(3) 0.075(3) -0.111(3) -0.137(4) C2 0.090(3) 0.066(2) 0.0519(19) 0.0182(16) -0.0370(19) -0.041(2) C12 0.0385(14) 0.0457(16) 0.0562(17) -0.0069(13) -0.0087(12) -0.0108(12) C11 0.0535(18) 0.0495(17) 0.0593(19) -0.0188(15) -0.0025(15) -0.0121(14) C7 0.0489(19) 0.069(2) 0.082(3) -0.029(2) -0.0021(18) -0.0051(16) C13 0.0412(18) 0.074(3) 0.122(4) -0.034(3) -0.006(2) -0.0088(17) C10 0.082(3) 0.080(3) 0.087(3) -0.034(2) -0.015(2) -0.037(2) C23 0.158(5) 0.084(3) 0.048(2) -0.006(2) -0.033(3) -0.049(3) C1 0.078(3) 0.081(3) 0.063(2) 0.027(2) -0.033(2) -0.034(2) C20 0.079(3) 0.123(4) 0.075(3) -0.031(3) -0.024(2) 0.018(3) C26 0.070(3) 0.102(4) 0.109(4) -0.055(3) -0.023(3) 0.012(2) F1 0.241(6) 0.135(4) 0.176(5) 0.069(4) 0.054(4) 0.102(4) 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' Br Br -0.2901 2.4595 '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' 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 C3 O1 C2 118.1(3) . . ? C28 N1 H1 125.8 . . ? C3 N1 H1 125.8 . . ? C3 N1 C28 108.4(2) . . ? N1 C28 C14 107.0(2) . . ? N1 C28 C27 130.6(3) . . ? C27 C28 C14 122.4(3) . . ? C3 C4 C14 104.4(2) . . ? C3 C4 C5 130.6(3) . . ? C14 C4 C5 125.0(2) . . ? O1 C3 N1 114.3(3) . . ? O1 C3 C4 134.0(3) . . ? C4 C3 N1 111.7(3) . . ? C28 C14 C4 108.5(2) . . ? C15 C14 C28 119.0(3) . . ? C15 C14 C4 132.5(3) . . ? C25 C18 C17 119.3(3) . . ? C25 C18 C19 119.8(3) . . ? C19 C18 C17 120.8(3) . . ? C6 C5 C4 120.4(3) . . ? C12 C5 C4 120.7(2) . . ? C12 C5 C6 118.8(3) . . ? C27 C17 C18 120.8(3) . . ? C27 C17 C16 118.4(3) . . ? C16 C17 C18 120.8(3) . . ? C5 C6 C7 121.2(3) . . ? C8 C6 C5 119.2(3) . . ? C8 C6 C7 119.5(3) . . ? C28 C27 C17 118.8(3) . . ? C28 C27 H27 120.6 . . ? C17 C27 H27 120.6 . . ? C14 C15 H15 121.0 . . ? C16 C15 C14 118.0(3) . . ? C16 C15 H15 121.0 . . ? C6 C8 H8 118.8 . . ? C9 C8 C6 122.5(3) . . ? C9 C8 H8 118.8 . . ? C18 C25 C24 118.7(3) . . ? C18 C25 C26 121.1(3) . . ? C24 C25 C26 120.2(4) . . ? C25 C24 H24 118.8 . . ? C22 C24 C25 122.3(4) . . ? C22 C24 H24 118.8 . . ? C8 C9 C11 117.8(3) . . ? C8 C9 C10 120.3(3) . . ? C11 C9 C10 121.9(3) . . ? C17 C16 Br1 119.2(2) . . ? C15 C16 Br1 117.4(2) . . ? C15 C16 C17 123.4(3) . . ? C19 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C22 C21 C19 121.9(3) . . ? C18 C19 C21 119.0(3) . . ? C18 C19 C20 121.1(3) . . ? C21 C19 C20 119.8(3) . . ? C24 C22 C21 118.1(3) . . ? C24 C22 C23 120.3(4) . . ? C21 C22 C23 121.6(4) . . ? O1 C2 H2 126.3 . . ? O1 C2 C1 107.5(3) . . ? C1 C2 H2 126.3 . . ? C5 C12 C13 121.2(3) . . ? C11 C12 C5 119.7(3) . . ? C11 C12 C13 119.2(3) . . ? C9 C11 C12 121.9(3) . . ? C9 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? F3 C1 F2 105.1(4) . . ? F3 C1 C2 114.7(4) . . ? F2 C1 C2 109.7(4) . . ? F1 C1 F3 106.4(6) . . ? F1 C1 F2 106.7(6) . . ? F1 C1 C2 113.7(5) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 Br1 C16 1.906(3) . ? O1 C3 1.353(4) . ? O1 C2 1.385(4) . ? N1 H1 0.8600 . ? N1 C28 1.373(4) . ? N1 C3 1.373(4) . ? C28 C14 1.410(4) . ? C28 C27 1.384(4) . ? F3 C1 1.275(5) . ? C4 C3 1.367(4) . ? C4 C14 1.439(4) . ? C4 C5 1.484(4) . ? C14 C15 1.394(4) . ? C18 C17 1.500(4) . ? C18 C25 1.391(5) . ? C18 C19 1.394(5) . ? C5 C6 1.411(4) . ? C5 C12 1.396(4) . ? C17 C27 1.387(4) . ? C17 C16 1.410(4) . ? C6 C8 1.384(4) . ? C6 C7 1.511(5) . ? C27 H27 0.9300 . ? C15 H15 0.9300 . ? C15 C16 1.379(4) . ? C8 H8 0.9300 . ? C8 C9 1.378(5) . ? C25 C24 1.395(5) . ? C25 C26 1.516(6) . ? C24 H24 0.9300 . ? C24 C22 1.371(6) . ? C9 C11 1.381(5) . ? C9 C10 1.504(5) . ? C21 H21 0.9300 . ? C21 C19 1.395(5) . ? C21 C22 1.372(6) . ? C19 C20 1.508(6) . ? C22 C23 1.517(5) . ? F2 C1 1.323(6) . ? C2 H2 0.9300 . ? C2 C1 1.486(5) . ? C12 C11 1.393(4) . ? C12 C13 1.514(5) . ? C11 H11 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C1 F1 1.237(7) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 O1 C2 C1 F3 52.0(6) . . . . ? O1 C2 C1 F2 170.0(5) . . . . ? O1 C2 C1 F1 -70.7(7) . . . . ? N1 C28 C14 C4 -0.7(4) . . . . ? N1 C28 C14 C15 179.8(3) . . . . ? N1 C28 C27 C17 179.6(3) . . . . ? C28 N1 C3 O1 179.1(3) . . . . ? C28 N1 C3 C4 -0.8(4) . . . . ? C28 C14 C15 C16 0.2(5) . . . . ? C4 C14 C15 C16 -179.3(3) . . . . ? C4 C5 C6 C8 -178.7(3) . . . . ? C4 C5 C6 C7 0.7(4) . . . . ? C4 C5 C12 C11 178.7(3) . . . . ? C4 C5 C12 C13 0.2(5) . . . . ? C3 O1 C2 C1 162.3(4) . . . . ? C3 N1 C28 C14 0.9(4) . . . . ? C3 N1 C28 C27 -178.1(3) . . . . ? C3 C4 C14 C28 0.2(3) . . . . ? C3 C4 C14 C15 179.7(4) . . . . ? C3 C4 C5 C6 -101.2(4) . . . . ? C3 C4 C5 C12 81.5(4) . . . . ? C14 C28 C27 C17 0.8(5) . . . . ? C14 C4 C3 O1 -179.5(4) . . . . ? C14 C4 C3 N1 0.3(4) . . . . ? C14 C4 C5 C6 81.7(4) . . . . ? C14 C4 C5 C12 -95.5(4) . . . . ? C14 C15 C16 Br1 180.0(2) . . . . ? C14 C15 C16 C17 1.2(5) . . . . ? C18 C17 C27 C28 -177.1(3) . . . . ? C18 C17 C16 Br1 -2.7(4) . . . . ? C18 C17 C16 C15 176.1(3) . . . . ? C18 C25 C24 C22 -0.2(5) . . . . ? C5 C4 C3 O1 2.9(7) . . . . ? C5 C4 C3 N1 -177.2(3) . . . . ? C5 C4 C14 C28 177.9(3) . . . . ? C5 C4 C14 C15 -2.6(5) . . . . ? C5 C6 C8 C9 1.2(4) . . . . ? C5 C12 C11 C9 -1.2(5) . . . . ? C17 C18 C25 C24 176.0(3) . . . . ? C17 C18 C25 C26 -1.5(5) . . . . ? C17 C18 C19 C21 -175.7(3) . . . . ? C17 C18 C19 C20 2.2(5) . . . . ? C6 C5 C12 C11 1.4(4) . . . . ? C6 C5 C12 C13 -177.0(3) . . . . ? C6 C8 C9 C11 -0.9(5) . . . . ? C6 C8 C9 C10 178.2(3) . . . . ? C27 C28 C14 C4 178.4(3) . . . . ? C27 C28 C14 C15 -1.2(5) . . . . ? C27 C17 C16 Br1 179.6(2) . . . . ? C27 C17 C16 C15 -1.6(5) . . . . ? C8 C9 C11 C12 0.9(5) . . . . ? C25 C18 C17 C27 96.9(4) . . . . ? C25 C18 C17 C16 -80.7(4) . . . . ? C25 C18 C19 C21 2.3(5) . . . . ? C25 C18 C19 C20 -179.8(4) . . . . ? C25 C24 C22 C21 2.2(5) . . . . ? C25 C24 C22 C23 -176.2(4) . . . . ? C16 C17 C27 C28 0.6(5) . . . . ? C19 C18 C17 C27 -85.1(4) . . . . ? C19 C18 C17 C16 97.4(4) . . . . ? C19 C18 C25 C24 -2.0(5) . . . . ? C19 C18 C25 C26 -179.5(4) . . . . ? C19 C21 C22 C24 -1.9(5) . . . . ? C19 C21 C22 C23 176.5(4) . . . . ? C22 C21 C19 C18 -0.3(5) . . . . ? C22 C21 C19 C20 -178.3(4) . . . . ? C2 O1 C3 N1 -170.7(4) . . . . ? C2 O1 C3 C4 9.2(7) . . . . ? C12 C5 C6 C8 -1.4(4) . . . . ? C12 C5 C6 C7 177.9(3) . . . . ? C7 C6 C8 C9 -178.2(3) . . . . ? C13 C12 C11 C9 177.3(4) . . . . ? C10 C9 C11 C12 -178.2(4) . . . . ? C26 C25 C24 C22 177.3(4) . . . . ?