#------------------------------------------------------------------------------ #$Date: 2020-02-27 07:24:25 +0200 (Thu, 27 Feb 2020) $ #$Revision: 248484 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557386.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_1557386 loop_ _publ_author_name 'Jyothi, Mane' 'Annadhasan, M.' 'Vuppu, Vinay Pradeep' 'Chandrasekar, Rajadurai' _publ_section_title ; Direct micro-scale monitoring of molecular aggregation, its growth and diffusion via aggregation-induced emission ; _journal_name_full 'Soft Matter' _journal_paper_doi 10.1039/D0SM00108B _journal_year 2020 _chemical_formula_moiety 'C23 H12 Br F6 N' _chemical_formula_sum 'C23 H12 Br F6 N' _chemical_formula_weight 496.25 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-12-13 deposited with the CCDC. 2020-02-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.113(9) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.327(4) _cell_length_b 9.854(2) _cell_length_c 28.274(7) _cell_measurement_reflns_used 4879 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 22.88 _cell_measurement_theta_min 2.48 _cell_volume 4141.4(17) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1168 _diffrn_reflns_av_unetI/netI 0.0730 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 29508 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.453 _diffrn_reflns_theta_min 2.480 _exptl_absorpt_coefficient_mu 2.048 _exptl_absorpt_correction_T_max 0.7912 _exptl_absorpt_correction_T_min 0.7094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.592 _exptl_crystal_description block _exptl_crystal_F_000 1968 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.747 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.077 _refine_ls_extinction_coef 0.0038(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 4256 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.1443 _refine_ls_R_factor_gt 0.0736 _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^)+(0.0688P)^2^+21.2989P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1628 _refine_ls_wR_factor_ref 0.1931 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2414 _reflns_number_total 4256 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sm00108b1.cif _cod_data_source_block shelx _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 1557386 _shelx_shelxl_version_number 2014/7 _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_min 0.709 _shelx_estimated_absorpt_t_max 0.791 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL RC48_0m_b.res in Cc New: C2/c CELL 0.71073 15.3270 9.8540 28.2740 90.000 104.113 90.000 ZERR 8 0.0040 0.0020 0.0070 0.000 0.009 0.000 LATT 7 SYMM - X , Y , 0.50000 - Z SFAC C Br F N H UNIT 184 8 48 8 96 L.S. 10 ACTA BOND $H FMAP 2 PLAN 10 SIZE 0.18 0.16 0.12 CONF WGHT 0.068800 21.298901 EXTI 0.003799 FVAR 0.23566 BR1 2 -0.215015 1.423930 -0.258664 11.00000 0.11586 0.06188 = 0.05589 0.01204 -0.00549 -0.00313 F7 3 -0.028115 0.431433 0.188372 11.00000 0.14553 0.15009 = 0.13212 0.02235 0.10660 0.02783 F8 3 0.063558 0.275731 0.209878 11.00000 0.08237 0.24528 = 0.12764 0.12545 0.04322 0.03048 F9 3 -0.044996 0.257312 0.147538 11.00000 0.10034 0.14915 = 0.12493 0.00017 0.05827 -0.05681 F10 3 0.348342 0.420348 0.096560 11.00000 0.08312 0.45315 = 0.29727 0.28859 0.11650 0.13460 F11 3 0.356430 0.409298 0.166106 11.00000 0.05582 0.36849 = 0.23991 -0.11575 -0.01891 0.05911 F12 3 0.325873 0.250892 0.129941 11.00000 0.10148 0.13220 = 0.35728 0.03916 0.08784 0.06430 C1 1 -0.204789 1.000654 -0.063618 11.00000 0.05233 0.05859 = 0.07761 0.02423 0.02227 0.01069 C1I 1 -0.108135 1.237702 -0.193073 11.00000 0.07331 0.08099 = 0.07499 0.02515 0.03497 0.00933 AFIX 43 H1I 5 -0.063960 1.259238 -0.209285 11.00000 -1.20000 AFIX 0 C2N 1 -0.191352 1.295370 -0.207429 11.00000 0.06741 0.04765 = 0.04045 -0.00018 0.00028 -0.00299 C3B 1 -0.255482 1.261950 -0.184301 11.00000 0.05203 0.06493 = 0.06863 0.01050 0.00014 0.00922 AFIX 43 H3B 5 -0.312431 1.300503 -0.194066 11.00000 -1.20000 AFIX 0 C4O 1 -0.236795 1.170457 -0.146082 11.00000 0.04389 0.05941 = 0.06340 0.01205 0.01468 0.00574 AFIX 43 H4O 5 -0.281799 1.148617 -0.130485 11.00000 -1.20000 AFIX 0 C5 1 -0.153895 1.110992 -0.130500 11.00000 0.03734 0.04066 = 0.04894 -0.00303 0.00709 -0.00239 C6X 1 -0.089254 1.147233 -0.154452 11.00000 0.04763 0.07799 = 0.08184 0.03038 0.01835 0.01551 AFIX 43 H6X 5 -0.031860 1.110277 -0.144510 11.00000 -1.20000 AFIX 0 C7T 1 -0.134768 1.013352 -0.089266 11.00000 0.03684 0.03720 = 0.04898 -0.00287 0.01252 -0.00233 C8K 1 -0.058628 0.942739 -0.075216 11.00000 0.04108 0.04659 = 0.04575 0.00026 0.01791 0.00176 AFIX 43 H8K 5 -0.017253 0.960844 -0.093600 11.00000 -1.20000 AFIX 0 C9D 1 -0.027141 0.842469 -0.036665 11.00000 0.03680 0.03979 = 0.04006 -0.00303 0.01145 0.00530 C10 1 -0.077981 0.785451 -0.007149 11.00000 0.03797 0.06326 = 0.07793 0.01965 0.02443 0.00596 AFIX 43 H10 5 -0.137599 0.811739 -0.011082 11.00000 -1.20000 AFIX 0 C11 1 -0.041050 0.690278 0.027929 11.00000 0.04525 0.06365 = 0.07150 0.02742 0.02791 0.00733 AFIX 43 H11 5 -0.076994 0.653783 0.046907 11.00000 -1.20000 AFIX 0 C12Q 1 0.046931 0.647261 0.035923 11.00000 0.03529 0.03972 = 0.04241 -0.00449 0.00846 -0.00129 C13 1 0.096647 0.704096 0.006031 11.00000 0.03799 0.08045 = 0.06229 0.02613 0.02188 0.01885 AFIX 43 H13 5 0.156264 0.677889 0.009891 11.00000 -1.20000 AFIX 0 C14E 1 0.085822 0.545790 0.073990 11.00000 0.03655 0.03870 = 0.04001 -0.00168 0.01435 -0.00106 C15U 1 0.036847 0.489168 0.104418 11.00000 0.03079 0.06516 = 0.04767 0.00551 0.00924 0.00620 AFIX 43 H15U 5 -0.022959 0.514412 0.100505 11.00000 -1.20000 AFIX 0 C16Y 1 0.073988 0.397165 0.140058 11.00000 0.04393 0.06077 = 0.04498 0.00160 0.01568 0.00068 C17H 1 0.017880 0.339918 0.171908 11.00000 0.04528 0.09682 = 0.06249 0.03329 0.01841 0.01019 C18F 1 0.163125 0.358324 0.147507 11.00000 0.04853 0.04911 = 0.04044 0.00332 0.00678 -0.00052 AFIX 43 H18F 5 0.188681 0.296709 0.171868 11.00000 -1.20000 AFIX 0 C19 1 0.213005 0.413862 0.117655 11.00000 0.03867 0.05471 = 0.05939 0.00821 0.01387 0.00688 C20 1 0.175386 0.504166 0.081923 11.00000 0.04507 0.05437 = 0.05375 0.00544 0.02040 0.00147 AFIX 43 H20 5 0.210471 0.539153 0.062209 11.00000 -1.20000 AFIX 0 C21Q 1 0.308101 0.374555 0.124459 11.00000 0.05735 0.09851 = 0.09925 0.04669 0.02273 0.02198 C45 1 0.060253 0.797957 -0.029091 11.00000 0.04805 0.08687 = 0.05537 0.02867 0.02323 0.01375 AFIX 43 H45 5 0.095981 0.832769 -0.048492 11.00000 -1.20000 AFIX 0 N1 4 -0.262622 0.995493 -0.044243 11.00000 0.07071 0.10890 = 0.13347 0.04511 0.06600 0.02909 HKLF 4 1 -1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 -1.0000 REM RC48_0m_b.res in Cc New: C2/c REM R1 = 0.0736 for 2414 Fo > 4sig(Fo) and 0.1443 for all 4256 data REM 281 parameters refined using 0 restraints END WGHT 0.0676 21.5097 REM Highest difference peak 0.747, deepest hole -0.516, 1-sigma level 0.077 Q1 1 0.3062 0.3103 0.0806 11.00000 0.05 0.75 Q2 1 0.3546 0.4888 0.1283 11.00000 0.05 0.71 Q3 1 0.0342 0.2032 0.1737 11.00000 0.05 0.57 Q4 1 0.3392 0.3124 0.1624 11.00000 0.05 0.47 Q5 1 0.3769 0.4189 0.0904 11.00000 0.05 0.38 Q6 1 0.3499 0.3998 0.1814 11.00000 0.05 0.38 Q7 1 0.3128 0.2144 0.1309 11.00000 0.05 0.37 Q8 1 0.0467 0.3852 0.2094 11.00000 0.05 0.36 Q9 1 -0.1892 1.3430 -0.2517 11.00000 0.05 0.29 Q10 1 -0.1881 1.5055 -0.2517 11.00000 0.05 0.28 ; _shelx_res_checksum 57449 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.21501(6) 1.42393(7) -0.25866(2) 0.0824(4) Uani 1 1 d . . . . . F7 F -0.0281(4) 0.4314(6) 0.1884(2) 0.130(2) Uani 1 1 d . . . . . F8 F 0.0636(3) 0.2757(7) 0.2099(2) 0.149(3) Uani 1 1 d . . . . . F9 F -0.0450(3) 0.2573(6) 0.14754(19) 0.1195(18) Uani 1 1 d . . . . . F10 F 0.3483(4) 0.4203(11) 0.0966(3) 0.266(6) Uani 1 1 d . . . . . F11 F 0.3564(4) 0.4093(11) 0.1661(4) 0.231(5) Uani 1 1 d . . . . . F12 F 0.3259(4) 0.2509(7) 0.1299(4) 0.191(4) Uani 1 1 d . . . . . C1 C -0.2048(4) 1.0007(6) -0.0636(2) 0.0617(17) Uani 1 1 d . . . . . C1I C -0.1081(5) 1.2377(7) -0.1931(2) 0.0735(19) Uani 1 1 d . . . . . H1I H -0.0640 1.2592 -0.2093 0.088 Uiso 1 1 calc R U . . . C2N C -0.1914(4) 1.2954(6) -0.20743(19) 0.0541(15) Uani 1 1 d . . . . . C3B C -0.2555(4) 1.2619(6) -0.1843(2) 0.0644(17) Uani 1 1 d . . . . . H3B H -0.3124 1.3005 -0.1941 0.077 Uiso 1 1 calc R U . . . C4O C -0.2368(4) 1.1705(6) -0.1461(2) 0.0553(15) Uani 1 1 d . . . . . H4O H -0.2818 1.1486 -0.1305 0.066 Uiso 1 1 calc R U . . . C5 C -0.1539(3) 1.1110(5) -0.13050(19) 0.0429(13) Uani 1 1 d . . . . . C6X C -0.0893(4) 1.1472(7) -0.1545(2) 0.0687(18) Uani 1 1 d . . . . . H6X H -0.0319 1.1103 -0.1445 0.082 Uiso 1 1 calc R U . . . C7T C -0.1348(3) 1.0134(5) -0.08927(18) 0.0406(12) Uani 1 1 d . . . . . C8K C -0.0586(4) 0.9427(5) -0.07522(18) 0.0432(12) Uani 1 1 d . . . . . H8K H -0.0173 0.9608 -0.0936 0.052 Uiso 1 1 calc R U . . . C9D C -0.0271(3) 0.8425(5) -0.03666(17) 0.0385(12) Uani 1 1 d . . . . . C10 C -0.0780(4) 0.7855(6) -0.0071(2) 0.0579(16) Uani 1 1 d . . . . . H10 H -0.1376 0.8117 -0.0111 0.070 Uiso 1 1 calc R U . . . C11 C -0.0410(4) 0.6903(6) 0.0279(2) 0.0578(16) Uani 1 1 d . . . . . H11 H -0.0770 0.6538 0.0469 0.069 Uiso 1 1 calc R U . . . C12Q C 0.0469(3) 0.6473(5) 0.03592(18) 0.0393(12) Uani 1 1 d . . . . . C13 C 0.0966(4) 0.7041(6) 0.0060(2) 0.0586(16) Uani 1 1 d . . . . . H13 H 0.1563 0.6779 0.0099 0.070 Uiso 1 1 calc R U . . . C14E C 0.0858(3) 0.5458(5) 0.07399(17) 0.0376(12) Uani 1 1 d . . . . . C15U C 0.0368(4) 0.4892(6) 0.10442(19) 0.0479(13) Uani 1 1 d . . . . . H15U H -0.0230 0.5144 0.1005 0.058 Uiso 1 1 calc R U . . . C16Y C 0.0740(4) 0.3972(6) 0.14006(19) 0.0491(14) Uani 1 1 d . . . . . C17H C 0.0179(4) 0.3399(8) 0.1719(2) 0.0673(19) Uani 1 1 d . . . . . C18F C 0.1631(4) 0.3583(6) 0.14751(18) 0.0467(13) Uani 1 1 d . . . . . H18F H 0.1887 0.2967 0.1719 0.056 Uiso 1 1 calc R U . . . C19 C 0.2130(4) 0.4139(6) 0.1177(2) 0.0506(14) Uani 1 1 d . . . . . C20 C 0.1754(4) 0.5042(6) 0.0819(2) 0.0496(14) Uani 1 1 d . . . . . H20 H 0.2105 0.5392 0.0622 0.060 Uiso 1 1 calc R U . . . C21Q C 0.3081(5) 0.3746(9) 0.1245(3) 0.084(2) Uani 1 1 d . . . . . C45 C 0.0603(4) 0.7980(7) -0.0291(2) 0.0616(17) Uani 1 1 d . . . . . H45 H 0.0960 0.8328 -0.0485 0.074 Uiso 1 1 calc R U . . . N1 N -0.2626(4) 0.9955(7) -0.0442(3) 0.097(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 Br1 0.1159(7) 0.0619(5) 0.0559(4) 0.0120(3) -0.0055(4) -0.0031(4) F7 0.146(5) 0.150(5) 0.132(4) 0.022(4) 0.107(4) 0.028(4) F8 0.082(3) 0.245(7) 0.128(4) 0.125(5) 0.043(3) 0.030(4) F9 0.100(4) 0.149(4) 0.125(4) 0.000(3) 0.058(3) -0.057(3) F10 0.083(4) 0.453(14) 0.297(10) 0.289(11) 0.117(6) 0.135(6) F11 0.056(3) 0.368(14) 0.240(9) -0.116(9) -0.019(5) 0.059(5) F12 0.101(4) 0.132(5) 0.357(12) 0.039(6) 0.088(6) 0.064(4) C1 0.052(4) 0.059(4) 0.078(4) 0.024(3) 0.022(3) 0.011(3) C1I 0.073(5) 0.081(5) 0.075(4) 0.025(4) 0.035(4) 0.009(4) C2N 0.067(4) 0.048(3) 0.040(3) 0.000(2) 0.000(3) -0.003(3) C3B 0.052(4) 0.065(4) 0.069(4) 0.011(3) 0.000(3) 0.009(3) C4O 0.044(3) 0.059(4) 0.063(4) 0.012(3) 0.015(3) 0.006(3) C5 0.037(3) 0.041(3) 0.049(3) -0.003(2) 0.007(3) -0.002(2) C6X 0.048(4) 0.078(4) 0.082(4) 0.030(4) 0.018(3) 0.016(3) C7T 0.037(3) 0.037(3) 0.049(3) -0.003(2) 0.013(2) -0.002(2) C8K 0.041(3) 0.047(3) 0.046(3) 0.000(2) 0.018(2) 0.002(3) C9D 0.037(3) 0.040(3) 0.040(3) -0.003(2) 0.011(2) 0.005(2) C10 0.038(3) 0.063(4) 0.078(4) 0.020(3) 0.024(3) 0.006(3) C11 0.045(4) 0.064(4) 0.072(4) 0.027(3) 0.028(3) 0.007(3) C12Q 0.035(3) 0.040(3) 0.042(3) -0.004(2) 0.008(2) -0.001(2) C13 0.038(3) 0.080(4) 0.062(4) 0.026(3) 0.022(3) 0.019(3) C14E 0.037(3) 0.039(3) 0.040(3) -0.002(2) 0.014(2) -0.001(2) C15U 0.031(3) 0.065(4) 0.048(3) 0.006(3) 0.009(2) 0.006(3) C16Y 0.044(3) 0.061(4) 0.045(3) 0.002(3) 0.016(3) 0.001(3) C17H 0.045(4) 0.097(5) 0.062(4) 0.033(4) 0.018(3) 0.010(4) C18F 0.049(4) 0.049(3) 0.040(3) 0.003(2) 0.007(3) -0.001(3) C19 0.039(3) 0.055(3) 0.059(3) 0.008(3) 0.014(3) 0.007(3) C20 0.045(3) 0.054(3) 0.054(3) 0.005(3) 0.020(3) 0.001(3) C21Q 0.057(5) 0.099(6) 0.099(6) 0.047(5) 0.023(5) 0.022(4) C45 0.048(4) 0.087(4) 0.055(3) 0.029(3) 0.023(3) 0.014(3) N1 0.071(4) 0.109(5) 0.133(6) 0.045(4) 0.066(4) 0.029(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' 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' H H 0.0000 0.0000 '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 N1 C1 C7T 176.9(7) . . ? C2N C1I C6X 120.2(6) . . ? C2N C1I H1I 119.9 . . ? C6X C1I H1I 119.9 . . ? C3B C2N C1I 119.6(6) . . ? C3B C2N Br1 120.6(5) . . ? C1I C2N Br1 119.8(5) . . ? C2N C3B C4O 120.1(6) . . ? C2N C3B H3B 119.9 . . ? C4O C3B H3B 119.9 . . ? C5 C4O C3B 121.9(6) . . ? C5 C4O H4O 119.0 . . ? C3B C4O H4O 119.0 . . ? C4O C5 C6X 116.9(5) . . ? C4O C5 C7T 121.3(5) . . ? C6X C5 C7T 121.8(5) . . ? C5 C6X C1I 121.2(6) . . ? C5 C6X H6X 119.4 . . ? C1I C6X H6X 119.4 . . ? C8K C7T C1 120.7(5) . . ? C8K C7T C5 124.3(5) . . ? C1 C7T C5 115.0(5) . . ? C7T C8K C9D 132.9(5) . . ? C7T C8K H8K 113.6 . . ? C9D C8K H8K 113.6 . . ? C45 C9D C10 116.4(5) . . ? C45 C9D C8K 117.6(5) . . ? C10 C9D C8K 126.0(5) . . ? C11 C10 C9D 120.9(5) . . ? C11 C10 H10 119.6 . . ? C9D C10 H10 119.6 . . ? C12Q C11 C10 122.6(5) . . ? C12Q C11 H11 118.7 . . ? C10 C11 H11 118.7 . . ? C11 C12Q C13 115.9(5) . . ? C11 C12Q C14E 122.0(5) . . ? C13 C12Q C14E 122.1(5) . . ? C45 C13 C12Q 121.8(5) . . ? C45 C13 H13 119.1 . . ? C12Q C13 H13 119.1 . . ? C15U C14E C20 116.1(5) . . ? C15U C14E C12Q 122.5(5) . . ? C20 C14E C12Q 121.3(5) . . ? C16Y C15U C14E 122.0(5) . . ? C16Y C15U H15U 119.0 . . ? C14E C15U H15U 119.0 . . ? C15U C16Y C18F 120.8(5) . . ? C15U C16Y C17H 119.6(5) . . ? C18F C16Y C17H 119.6(5) . . ? F8 C17H F7 105.8(7) . . ? F8 C17H F9 108.1(7) . . ? F7 C17H F9 103.0(6) . . ? F8 C17H C16Y 114.1(5) . . ? F7 C17H C16Y 113.3(6) . . ? F9 C17H C16Y 111.8(6) . . ? C19 C18F C16Y 118.0(5) . . ? C19 C18F H18F 121.0 . . ? C16Y C18F H18F 121.0 . . ? C20 C19 C18F 120.9(5) . . ? C20 C19 C21Q 119.6(6) . . ? C18F C19 C21Q 119.5(5) . . ? C19 C20 C14E 122.1(5) . . ? C19 C20 H20 118.9 . . ? C14E C20 H20 118.9 . . ? F10 C21Q F12 108.4(9) . . ? F10 C21Q F11 103.3(10) . . ? F12 C21Q F11 95.0(8) . . ? F10 C21Q C19 117.7(6) . . ? F12 C21Q C19 116.8(8) . . ? F11 C21Q C19 112.5(8) . . ? C13 C45 C9D 122.4(5) . . ? C13 C45 H45 118.8 . . ? C9D C45 H45 118.8 . . ? 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 C2N 1.892(6) . ? F7 C17H 1.299(8) . ? F8 C17H 1.295(7) . ? F9 C17H 1.320(8) . ? F10 C21Q 1.201(8) . ? F11 C21Q 1.276(10) . ? F12 C21Q 1.250(9) . ? C1 N1 1.151(8) . ? C1 C7T 1.440(8) . ? C1I C2N 1.365(9) . ? C1I C6X 1.384(8) . ? C1I H1I 0.9300 . ? C2N C3B 1.347(9) . ? C3B C4O 1.383(8) . ? C3B H3B 0.9300 . ? C4O C5 1.371(7) . ? C4O H4O 0.9300 . ? C5 C6X 1.377(8) . ? C5 C7T 1.485(7) . ? C6X H6X 0.9300 . ? C7T C8K 1.333(7) . ? C8K C9D 1.463(7) . ? C8K H8K 0.9300 . ? C9D C45 1.376(7) . ? C9D C10 1.392(7) . ? C10 C11 1.382(8) . ? C10 H10 0.9300 . ? C11 C12Q 1.379(7) . ? C11 H11 0.9300 . ? C12Q C13 1.387(7) . ? C12Q C14E 1.483(7) . ? C13 C45 1.372(8) . ? C13 H13 0.9300 . ? C14E C15U 1.389(7) . ? C14E C20 1.397(7) . ? C15U C16Y 1.372(7) . ? C15U H15U 0.9300 . ? C16Y C18F 1.385(8) . ? C16Y C17H 1.499(8) . ? C18F C19 1.382(7) . ? C18F H18F 0.9300 . ? C19 C20 1.364(7) . ? C19 C21Q 1.475(9) . ? C20 H20 0.9300 . ? C45 H45 0.9300 . ? 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 C6X C1I C2N C3B -1.1(10) . . . . ? C6X C1I C2N Br1 177.7(5) . . . . ? C1I C2N C3B C4O 0.4(9) . . . . ? Br1 C2N C3B C4O -178.4(5) . . . . ? C2N C3B C4O C5 -0.1(9) . . . . ? C3B C4O C5 C6X 0.5(9) . . . . ? C3B C4O C5 C7T 179.7(5) . . . . ? C4O C5 C6X C1I -1.2(9) . . . . ? C7T C5 C6X C1I 179.6(6) . . . . ? C2N C1I C6X C5 1.5(11) . . . . ? C4O C5 C7T C8K 173.6(5) . . . . ? C6X C5 C7T C8K -7.2(8) . . . . ? C4O C5 C7T C1 -7.7(7) . . . . ? C6X C5 C7T C1 171.5(6) . . . . ? C1 C7T C8K C9D 2.0(9) . . . . ? C5 C7T C8K C9D -179.3(5) . . . . ? C7T C8K C9D C45 -173.9(6) . . . . ? C7T C8K C9D C10 7.3(9) . . . . ? C45 C9D C10 C11 0.5(9) . . . . ? C8K C9D C10 C11 179.4(6) . . . . ? C9D C10 C11 C12Q 0.4(10) . . . . ? C10 C11 C12Q C13 -0.8(9) . . . . ? C10 C11 C12Q C14E 179.5(6) . . . . ? C11 C12Q C13 C45 0.4(9) . . . . ? C14E C12Q C13 C45 -180.0(6) . . . . ? C11 C12Q C14E C15U -1.0(8) . . . . ? C13 C12Q C14E C15U 179.4(5) . . . . ? C11 C12Q C14E C20 -179.4(5) . . . . ? C13 C12Q C14E C20 0.9(8) . . . . ? C20 C14E C15U C16Y -0.3(8) . . . . ? C12Q C14E C15U C16Y -178.8(5) . . . . ? C14E C15U C16Y C18F 0.9(9) . . . . ? C14E C15U C16Y C17H 179.8(6) . . . . ? C15U C16Y C17H F8 -167.2(7) . . . . ? C18F C16Y C17H F8 11.7(10) . . . . ? C15U C16Y C17H F7 -46.0(9) . . . . ? C18F C16Y C17H F7 132.9(6) . . . . ? C15U C16Y C17H F9 69.8(8) . . . . ? C18F C16Y C17H F9 -111.3(6) . . . . ? C15U C16Y C18F C19 -0.7(8) . . . . ? C17H C16Y C18F C19 -179.6(6) . . . . ? C16Y C18F C19 C20 0.0(8) . . . . ? C16Y C18F C19 C21Q -179.8(6) . . . . ? C18F C19 C20 C14E 0.6(9) . . . . ? C21Q C19 C20 C14E -179.6(6) . . . . ? C15U C14E C20 C19 -0.4(8) . . . . ? C12Q C14E C20 C19 178.1(5) . . . . ? C20 C19 C21Q F10 -2.9(14) . . . . ? C18F C19 C21Q F10 176.9(10) . . . . ? C20 C19 C21Q F12 -134.6(9) . . . . ? C18F C19 C21Q F12 45.2(12) . . . . ? C20 C19 C21Q F11 117.0(9) . . . . ? C18F C19 C21Q F11 -63.2(11) . . . . ? C12Q C13 C45 C9D 0.6(10) . . . . ? C10 C9D C45 C13 -1.0(9) . . . . ? C8K C9D C45 C13 -179.9(6) . . . . ?