#------------------------------------------------------------------------------ #$Date: 2021-01-04 20:18:39 +0200 (Mon, 04 Jan 2021) $ #$Revision: 260473 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/77/7127758.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_7127758 loop_ _publ_author_name 'Yan, Cai-Xin' 'Lin, Qian-Qian' 'Li, Sha' 'Wu, Cheng-Juan' 'Li, Yan-An' 'Fan, Jian-Zhong' 'Ma, Jian-Ping' 'Geng, Yan' 'Dong, Yu-Bin' _publ_section_title ; Synthesis of fulvene-containing boron complexes with aggregation-induced emission and mechanochromic luminescence. ; _journal_issue 92 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 14435 _journal_page_last 14438 _journal_paper_doi 10.1039/d0cc05757f _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C25 H25 B F2 O4' _chemical_formula_sum 'C25 H25 B F2 O4' _chemical_formula_weight 438.26 _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 direct _atom_sites_solution_secondary difmap _audit_creation_date 2018-08-30 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _audit_update_record ; 2019-05-08 deposited with the CCDC. 2020-10-22 downloaded from the CCDC. ; _cell_angle_alpha 101.355(6) _cell_angle_beta 97.002(6) _cell_angle_gamma 104.391(6) _cell_formula_units_Z 2 _cell_length_a 7.8130(6) _cell_length_b 9.3837(6) _cell_length_c 16.3462(11) _cell_measurement_reflns_used 2430 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.6480 _cell_measurement_theta_min 10.3100 _cell_volume 1119.53(14) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0793 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.9985 _diffrn_measured_fraction_theta_max 0.9784 _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 11.00 80.00 1.00 1.10 -- 54.00 -37.00 -30.00 69 2 \w 36.00 124.00 1.00 1.10 -- 54.00 37.00 0.00 88 3 \w 142.00 168.00 1.00 1.10 -- 108.00 63.00 -60.00 26 4 \w 117.00 142.00 1.00 1.10 -- 108.00 -25.00 -60.00 25 5 \w 93.00 127.00 1.00 1.10 -- 108.00 -37.00 -60.00 34 6 \w 88.00 114.00 1.00 1.10 -- 108.00-111.00 30.00 26 7 \w 65.00 113.00 1.00 1.10 -- 108.00-111.00 -90.00 48 8 \w 55.00 81.00 1.00 1.10 -- 54.00-125.00-180.00 26 9 \w 38.00 127.00 1.00 1.10 -- 108.00 -50.00-180.00 89 10 \w 51.00 79.00 1.00 1.10 -- 108.00 -37.00 -60.00 28 11 \w 38.00 131.00 1.00 1.10 -- 108.00 -77.00 -60.00 93 12 \w 44.00 111.00 1.00 1.10 -- 54.00-125.00 -30.00 67 13 \w 39.00 129.00 1.00 1.10 -- 108.00 -50.00 60.00 90 14 \w 88.00 155.00 1.00 1.10 -- 108.00 63.00 -30.00 67 15 \w 37.00 145.00 1.00 1.10 -- 108.00 -91.00 90.00 108 16 \w 36.00 175.00 1.00 1.10 -- 108.00 12.00 -60.00 139 17 \w 35.00 86.00 1.00 1.10 -- 108.00 -25.00 -60.00 51 18 \w 23.00 48.00 1.00 1.10 -- 54.00 -57.00 -60.00 25 19 \w -2.00 30.00 1.00 1.00 -- 0.00 -77.00-120.00 32 20 \w -10.00 80.00 1.00 1.10 -- 54.00 -37.00-180.00 90 21 \w 24.00 72.00 1.00 1.10 -- 54.00-125.00-150.00 48 22 \w -69.00 -13.00 1.00 1.00 -- 0.00 -77.00-120.00 56 23 \w 25.00 70.00 1.00 1.00 -- 0.00 77.00 -60.00 45 24 \w 31.00 104.00 1.00 1.10 -- 54.00 37.00 150.00 73 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1340833000 _diffrn_orient_matrix_UB_12 -0.1424427000 _diffrn_orient_matrix_UB_13 0.0116589000 _diffrn_orient_matrix_UB_21 0.1338124000 _diffrn_orient_matrix_UB_22 -0.0045540000 _diffrn_orient_matrix_UB_23 0.0762372000 _diffrn_orient_matrix_UB_31 -0.0833178000 _diffrn_orient_matrix_UB_32 0.1005777000 _diffrn_orient_matrix_UB_33 0.0600130000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_unetI/netI 0.0276 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7135 _diffrn_reflns_theta_full 67.05 _diffrn_reflns_theta_max 67.05 _diffrn_reflns_theta_min 5.01 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.807 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 460 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.124 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 294 _refine_ls_number_reflns 4003 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0403 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.2060P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1002 _refine_ls_wR_factor_ref 0.1118 _reflns_number_gt 3093 _reflns_number_total 4005 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d0cc05757f2.cif _cod_data_source_block exp_2837 _cod_original_cell_volume 1119.52(13) _cod_database_code 7127758 _chemical_oxdiff_formula 'C1 H1 N1 O1 B1 F1' _reflns_odcompleteness_completeness 99.85 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C12(H12), C16(H16), C17(H17), C19(H19), C20(H20) 2.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B, H24C), C25(H25A,H25B,H25C) ; _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.010 _oxdiff_exptl_absorpt_empirical_full_min 0.825 _shelx_res_file ; TITL exp_2837 in P-1 #2 CELL 1.54184 7.81295 9.38374 16.34616 101.3549 97.0022 104.391 ZERR 2 0.00055 0.00062 0.00109 0.0056 0.0057 0.0059 LATT 1 SFAC C H B F O UNIT 50 50 2 4 8 L.S. 4 ACTA BOND $H FMAP 2 PLAN 20 conf htab 2 WGHT 0.050100 0.206900 FVAR 7.740110 B1 3 1.289379 0.466726 0.303797 11.000000 0.058260 0.039590 = 0.050910 0.001400 0.001130 -0.000300 C1 1 1.247635 0.458082 -0.210871 11.000000 0.085120 0.073580 = 0.061440 0.028650 0.021750 0.018610 AFIX 137 H1A 2 1.200411 0.543077 -0.196368 11.000000 -1.500000 H1B 2 1.241612 0.431261 -0.271150 11.000000 -1.500000 H1C 2 1.370408 0.484303 -0.182852 11.000000 -1.500000 AFIX 0 C2 1 1.144794 0.342598 -0.100568 11.000000 0.044670 0.048980 = 0.046400 0.010510 0.008400 0.012300 C3 1 1.051947 0.211071 -0.080306 11.000000 0.050730 0.041150 = 0.047230 -0.001530 0.008770 0.002070 AFIX 43 H3 2 0.993294 0.125460 -0.123266 11.000000 -1.200000 AFIX 0 C4 1 1.046553 0.207121 0.002456 11.000000 0.047090 0.032960 = 0.050890 0.006110 0.012080 0.003630 AFIX 43 H4 2 0.983943 0.118175 0.014860 11.000000 -1.200000 AFIX 0 C5 1 1.132705 0.333314 0.069078 11.000000 0.039430 0.033490 = 0.045770 0.008340 0.006520 0.007430 C6 1 1.226262 0.463654 0.047196 11.000000 0.053000 0.034010 = 0.050320 0.006270 0.001700 -0.000720 AFIX 43 H6 2 1.286269 0.549080 0.090038 11.000000 -1.200000 AFIX 0 C7 1 1.232274 0.469400 -0.036043 11.000000 0.058620 0.038590 = 0.052380 0.013940 0.008450 0.002080 AFIX 43 H7 2 1.294759 0.557977 -0.048861 11.000000 -1.200000 AFIX 0 C8 1 1.136082 0.328114 0.157972 11.000000 0.040000 0.032760 = 0.045610 0.004360 0.004060 0.007440 C9 1 1.003864 0.228141 0.186132 11.000000 0.037950 0.036620 = 0.039340 0.005860 0.004180 0.008210 C10 1 0.825742 0.154750 0.142612 11.000000 0.038410 0.040800 = 0.038100 0.007620 0.002690 0.009170 AFIX 43 H10 2 0.777945 0.165629 0.089993 11.000000 -1.200000 AFIX 0 C11 1 0.732279 0.063937 0.189820 11.000000 0.036080 0.038970 = 0.037700 0.004760 0.005060 0.008610 C12 1 0.852571 0.073332 0.262438 11.000000 0.039700 0.044420 = 0.035990 0.007350 0.006490 0.007620 AFIX 43 H12 2 0.826085 0.020234 0.303844 11.000000 -1.200000 AFIX 0 C13 1 1.020183 0.175063 0.263927 11.000000 0.038330 0.041270 = 0.036490 0.003900 0.003690 0.006770 C14 1 1.169824 0.212446 0.329169 11.000000 0.038260 0.044670 = 0.037260 0.002160 0.004420 0.007570 C15 1 1.191844 0.118455 0.388438 11.000000 0.039070 0.048680 = 0.035580 0.004210 0.001880 0.009140 C16 1 1.129432 -0.038759 0.364229 11.000000 0.048500 0.052720 = 0.035060 0.001270 0.000260 0.011430 AFIX 43 H16 2 1.066877 -0.085094 0.309416 11.000000 -1.200000 AFIX 0 C17 1 1.158076 -0.127426 0.419505 11.000000 0.061000 0.048010 = 0.044090 0.004130 0.006070 0.013870 AFIX 43 H17 2 1.116170 -0.232374 0.401967 11.000000 -1.200000 AFIX 0 C18 1 1.249870 -0.058860 0.501457 11.000000 0.058880 0.060560 = 0.037560 0.011580 0.008440 0.020120 C19 1 1.313643 0.098834 0.526995 11.000000 0.063980 0.061340 = 0.035270 0.002480 -0.004150 0.011610 AFIX 43 H19 2 1.374427 0.144910 0.582132 11.000000 -1.200000 AFIX 0 C20 1 1.286990 0.185672 0.471190 11.000000 0.052670 0.051100 = 0.039510 0.002110 -0.001890 0.006210 AFIX 43 H20 2 1.332463 0.290443 0.488313 11.000000 -1.200000 AFIX 0 C21 1 1.223999 -0.294866 0.540709 11.000000 0.139570 0.069220 = 0.068350 0.025780 0.011290 0.034700 AFIX 137 H21A 2 1.095291 -0.325672 0.526085 11.000000 -1.500000 H21B 2 1.260467 -0.332191 0.588665 11.000000 -1.500000 H21C 2 1.273552 -0.335267 0.493423 11.000000 -1.500000 AFIX 0 C22 1 0.534109 -0.020290 0.167657 11.000000 0.034600 0.045990 = 0.043240 0.009440 0.003970 0.005890 C23 1 0.476097 -0.107942 0.233763 11.000000 0.046350 0.089600 = 0.057880 0.027800 0.007650 -0.004450 AFIX 137 H23A 2 0.545813 -0.178095 0.237948 11.000000 -1.500000 H23B 2 0.351082 -0.162392 0.217063 11.000000 -1.500000 H23C 2 0.494941 -0.038421 0.287820 11.000000 -1.500000 AFIX 0 C24 1 0.427619 0.095679 0.162858 11.000000 0.041440 0.061470 = 0.092410 0.005190 0.007980 0.016650 AFIX 137 H24A 2 0.451576 0.165975 0.216993 11.000000 -1.500000 H24B 2 0.301537 0.044229 0.147928 11.000000 -1.500000 H24C 2 0.463060 0.149452 0.120646 11.000000 -1.500000 AFIX 0 C25 1 0.494827 -0.132882 0.081374 11.000000 0.048000 0.048320 = 0.050480 0.006370 -0.000230 0.001820 AFIX 137 H25A 2 0.539487 -0.080844 0.039958 11.000000 -1.500000 H25B 2 0.367524 -0.177597 0.064450 11.000000 -1.500000 H25C 2 0.552850 -0.210769 0.085638 11.000000 -1.500000 AFIX 0 F1 4 1.448360 0.575952 0.334831 11.000000 0.078670 0.057260 = 0.063090 0.001490 -0.006940 -0.020500 F2 4 1.143481 0.513762 0.323192 11.000000 0.083580 0.054880 = 0.070220 -0.002900 0.013280 0.023650 O1 5 1.144130 0.332441 -0.184435 11.000000 0.076920 0.064020 = 0.046220 0.013070 0.013410 0.005100 O2 5 1.276834 0.423174 0.209868 11.000000 0.046450 0.042630 = 0.047470 0.006430 0.001340 -0.003110 O3 5 1.301635 0.336569 0.341388 11.000000 0.044290 0.051770 = 0.044210 0.005280 -0.002720 -0.000310 O4 5 1.287347 -0.133800 0.561419 11.000000 0.099390 0.070040 = 0.045070 0.017910 0.007350 0.027290 Q1 1 1.233400 0.572700 0.113200 11.000000 0.050000 0.13 Q2 1 1.082100 0.279400 0.041900 11.000000 0.050000 0.12 Q3 1 1.069900 0.249300 0.165500 11.000000 0.050000 0.12 Q4 1 1.139400 -0.083200 0.294000 11.000000 0.050000 0.11 Q5 1 0.456100 0.014900 0.308900 11.000000 0.050000 0.11 Q6 1 0.532100 -0.080900 0.131300 11.000000 0.050000 0.11 Q7 1 1.026100 0.213300 0.232600 11.000000 0.050000 0.11 Q8 1 1.271500 0.144000 0.418600 11.000000 0.050000 0.11 Q9 1 0.942100 0.177500 0.158400 11.000000 0.050000 0.11 Q10 1 0.758300 0.134600 0.182900 11.000000 0.050000 0.11 Q11 1 1.321700 0.557500 -0.172400 11.000000 0.050000 0.11 Q12 1 0.452700 0.084400 0.256700 11.000000 0.050000 0.11 Q13 1 1.154100 -0.320300 0.598800 11.000000 0.050000 0.11 Q14 1 0.322900 0.044400 0.308100 11.000000 0.050000 0.10 Q15 1 0.747300 0.223700 0.099200 11.000000 0.050000 0.10 Q16 1 0.981600 0.091400 0.251000 11.000000 0.050000 0.10 Q17 1 0.648000 0.011100 0.179700 11.000000 0.050000 0.10 Q18 1 0.358900 -0.222300 0.082400 11.000000 0.050000 0.10 Q19 1 1.146100 0.234600 -0.256000 11.000000 0.050000 0.09 Q20 1 0.522300 -0.065500 0.305700 11.000000 0.050000 0.09 HKLF 4 END ; loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn B1 B 1.2894(3) 0.4667(2) 0.30378(14) 0.0542(6) Uani 1 1 d . . . C1 C 1.2476(3) 0.4581(3) -0.21090(15) 0.0715(6) Uani 1 1 d . . . H1A H 1.2004 0.5431 -0.1964 0.107 Uiso 1 1 calc . . GR H1B H 1.2415 0.4312 -0.2712 0.107 Uiso 1 1 calc . . GR H1C H 1.3704 0.4843 -0.1829 0.107 Uiso 1 1 calc . . GR C2 C 1.1448(2) 0.3426(2) -0.10059(12) 0.0470(4) Uani 1 1 d . . . C3 C 1.0520(3) 0.2111(2) -0.08028(12) 0.0501(5) Uani 1 1 d . . . H3 H 0.9933 0.1255 -0.1232 0.060 Uiso 1 1 calc . . R C4 C 1.0466(2) 0.20714(19) 0.00246(11) 0.0453(4) Uani 1 1 d . . . H4 H 0.9840 0.1182 0.0149 0.054 Uiso 1 1 calc . . R C5 C 1.1327(2) 0.33326(18) 0.06904(11) 0.0404(4) Uani 1 1 d . . . C6 C 1.2263(3) 0.46362(19) 0.04718(12) 0.0494(5) Uani 1 1 d . . . H6 H 1.2862 0.5491 0.0900 0.059 Uiso 1 1 calc . . R C7 C 1.2323(3) 0.4693(2) -0.03602(12) 0.0516(5) Uani 1 1 d . . . H7 H 1.2949 0.5579 -0.0488 0.062 Uiso 1 1 calc . . R C8 C 1.1361(2) 0.32807(18) 0.15794(11) 0.0408(4) Uani 1 1 d . . . C9 C 1.0039(2) 0.22815(18) 0.18616(10) 0.0392(4) Uani 1 1 d . . . C10 C 0.8257(2) 0.15475(18) 0.14263(11) 0.0402(4) Uani 1 1 d . . . H10 H 0.7779 0.1656 0.0900 0.048 Uiso 1 1 calc . . R C11 C 0.7323(2) 0.06395(18) 0.18983(10) 0.0386(4) Uani 1 1 d . . . C12 C 0.8525(2) 0.07332(19) 0.26242(10) 0.0411(4) Uani 1 1 d . . . H12 H 0.8261 0.0202 0.3038 0.049 Uiso 1 1 calc . . R C13 C 1.0202(2) 0.17506(19) 0.26389(10) 0.0406(4) Uani 1 1 d . . . C14 C 1.1698(2) 0.21247(19) 0.32917(10) 0.0420(4) Uani 1 1 d . . . C15 C 1.1918(2) 0.1185(2) 0.38846(10) 0.0430(4) Uani 1 1 d . . . C16 C 1.1294(2) -0.0388(2) 0.36428(11) 0.0478(4) Uani 1 1 d . . . H16 H 1.0669 -0.0851 0.3095 0.057 Uiso 1 1 calc . . R C17 C 1.1581(3) -0.1274(2) 0.41953(12) 0.0525(5) Uani 1 1 d . . . H17 H 1.1162 -0.2323 0.4020 0.063 Uiso 1 1 calc . . R C18 C 1.2499(3) -0.0588(2) 0.50143(11) 0.0519(5) Uani 1 1 d . . . C19 C 1.3136(3) 0.0988(2) 0.52699(12) 0.0572(5) Uani 1 1 d . . . H19 H 1.3743 0.1449 0.5821 0.069 Uiso 1 1 calc . . R C20 C 1.2870(3) 0.1856(2) 0.47118(11) 0.0515(5) Uani 1 1 d . . . H20 H 1.3325 0.2904 0.4883 0.062 Uiso 1 1 calc . . R C21 C 1.2240(4) -0.2949(3) 0.54070(16) 0.0907(9) Uani 1 1 d . . . H21A H 1.0953 -0.3257 0.5261 0.136 Uiso 1 1 calc . . GR H21B H 1.2604 -0.3322 0.5887 0.136 Uiso 1 1 calc . . GR H21C H 1.2735 -0.3353 0.4934 0.136 Uiso 1 1 calc . . GR C22 C 0.5341(2) -0.0203(2) 0.16765(11) 0.0428(4) Uani 1 1 d . . . C23 C 0.4760(3) -0.1079(3) 0.23374(13) 0.0676(6) Uani 1 1 d . . . H23A H 0.5457 -0.1781 0.2379 0.101 Uiso 1 1 calc . . GR H23B H 0.3510 -0.1622 0.2171 0.101 Uiso 1 1 calc . . GR H23C H 0.4950 -0.0383 0.2878 0.101 Uiso 1 1 calc . . GR C24 C 0.4277(3) 0.0957(2) 0.16288(16) 0.0671(6) Uani 1 1 d . . . H24A H 0.4516 0.1659 0.2170 0.101 Uiso 1 1 calc . . GR H24B H 0.3016 0.0443 0.1479 0.101 Uiso 1 1 calc . . GR H24C H 0.4632 0.1495 0.1207 0.101 Uiso 1 1 calc . . GR C25 C 0.4948(3) -0.1328(2) 0.08142(12) 0.0530(5) Uani 1 1 d . . . H25A H 0.5394 -0.0808 0.0400 0.079 Uiso 1 1 calc . . GR H25B H 0.3675 -0.1776 0.0645 0.079 Uiso 1 1 calc . . GR H25C H 0.5529 -0.2107 0.0857 0.079 Uiso 1 1 calc . . GR F1 F 1.44835(18) 0.57595(13) 0.33484(8) 0.0772(4) Uani 1 1 d . . . F2 F 1.14347(18) 0.51375(13) 0.32318(8) 0.0714(4) Uani 1 1 d . . . O1 O 1.1442(2) 0.33244(16) -0.18441(8) 0.0647(4) Uani 1 1 d . . . O2 O 1.27680(16) 0.42321(13) 0.20987(8) 0.0497(3) Uani 1 1 d . . . O3 O 1.30164(16) 0.33658(14) 0.34140(8) 0.0512(3) Uani 1 1 d . . . O4 O 1.2874(2) -0.13379(17) 0.56141(9) 0.0708(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 B1 0.0583(14) 0.0397(11) 0.0506(13) 0.0019(9) 0.0012(10) -0.0004(10) C1 0.0850(17) 0.0733(15) 0.0620(14) 0.0285(12) 0.0222(12) 0.0186(13) C2 0.0447(10) 0.0492(10) 0.0466(10) 0.0109(8) 0.0084(8) 0.0128(8) C3 0.0502(11) 0.0410(10) 0.0482(11) -0.0011(8) 0.0089(8) 0.0021(8) C4 0.0472(10) 0.0330(8) 0.0507(10) 0.0063(7) 0.0122(8) 0.0038(7) C5 0.0393(9) 0.0331(8) 0.0465(10) 0.0085(7) 0.0068(7) 0.0074(7) C6 0.0531(11) 0.0342(9) 0.0501(11) 0.0060(8) 0.0017(8) -0.0005(8) C7 0.0583(12) 0.0383(9) 0.0525(11) 0.0136(8) 0.0085(9) 0.0018(8) C8 0.0399(9) 0.0326(8) 0.0453(9) 0.0041(7) 0.0036(7) 0.0075(7) C9 0.0381(9) 0.0365(8) 0.0395(9) 0.0058(7) 0.0041(7) 0.0079(7) C10 0.0387(9) 0.0410(9) 0.0379(9) 0.0075(7) 0.0025(7) 0.0093(7) C11 0.0360(9) 0.0392(9) 0.0373(9) 0.0047(7) 0.0052(7) 0.0087(7) C12 0.0397(9) 0.0445(9) 0.0362(9) 0.0077(7) 0.0070(7) 0.0078(7) C13 0.0383(9) 0.0412(9) 0.0364(9) 0.0037(7) 0.0036(7) 0.0066(7) C14 0.0382(9) 0.0446(10) 0.0372(9) 0.0022(7) 0.0048(7) 0.0077(8) C15 0.0391(9) 0.0487(10) 0.0356(9) 0.0039(7) 0.0019(7) 0.0094(8) C16 0.0482(10) 0.0527(11) 0.0351(9) 0.0013(8) 0.0002(8) 0.0113(8) C17 0.0608(12) 0.0483(10) 0.0437(10) 0.0039(8) 0.0060(9) 0.0139(9) C18 0.0588(12) 0.0610(12) 0.0381(10) 0.0120(9) 0.0087(8) 0.0204(10) C19 0.0642(13) 0.0612(12) 0.0354(10) 0.0022(9) -0.0041(9) 0.0117(10) C20 0.0526(11) 0.0509(11) 0.0402(10) 0.0023(8) -0.0016(8) 0.0062(9) C21 0.139(3) 0.0688(16) 0.0692(16) 0.0258(13) 0.0113(16) 0.0344(17) C22 0.0347(9) 0.0460(10) 0.0435(9) 0.0095(8) 0.0039(7) 0.0060(7) C23 0.0460(11) 0.0894(16) 0.0585(13) 0.0279(11) 0.0074(9) -0.0043(11) C24 0.0411(11) 0.0620(13) 0.0927(17) 0.0053(12) 0.0083(11) 0.0165(10) C25 0.0480(11) 0.0486(11) 0.0510(11) 0.0066(9) -0.0004(8) 0.0017(9) F1 0.0786(9) 0.0572(7) 0.0633(8) 0.0015(6) -0.0069(6) -0.0204(6) F2 0.0834(9) 0.0550(7) 0.0704(8) -0.0028(6) 0.0134(7) 0.0235(6) O1 0.0767(10) 0.0639(9) 0.0463(8) 0.0131(7) 0.0135(7) 0.0052(7) O2 0.0465(7) 0.0427(7) 0.0475(7) 0.0065(5) 0.0014(6) -0.0030(6) O3 0.0440(7) 0.0519(7) 0.0445(7) 0.0053(6) -0.0027(5) -0.0003(6) O4 0.0992(12) 0.0703(10) 0.0454(8) 0.0182(7) 0.0074(8) 0.0275(9) 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' B B 0.0090 0.0039 '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' O O 0.0492 0.0322 '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 F1 B1 F2 113.11(18) . . ? F1 B1 O2 106.54(17) . . ? F1 B1 O3 106.27(18) . . ? F2 B1 O2 110.31(18) . . ? F2 B1 O3 110.22(17) . . ? O3 B1 O2 110.25(16) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? C7 C2 C3 119.34(17) . . ? O1 C2 C3 115.15(16) . . ? O1 C2 C7 125.49(17) . . ? C2 C3 H3 119.9 . . ? C4 C3 C2 120.29(16) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 119.1 . . ? C3 C4 C5 121.77(16) . . ? C5 C4 H4 119.1 . . ? C4 C5 C8 122.28(15) . . ? C6 C5 C4 116.93(16) . . ? C6 C5 C8 120.67(15) . . ? C5 C6 H6 119.0 . . ? C7 C6 C5 121.90(16) . . ? C7 C6 H6 119.0 . . ? C2 C7 H7 120.1 . . ? C6 C7 C2 119.76(17) . . ? C6 C7 H7 120.1 . . ? C9 C8 C5 123.72(15) . . ? O2 C8 C5 114.14(14) . . ? O2 C8 C9 122.12(16) . . ? C8 C9 C10 126.26(16) . . ? C8 C9 C13 127.99(15) . . ? C10 C9 C13 105.74(14) . . ? C9 C10 H10 124.8 . . ? C11 C10 C9 110.38(15) . . ? C11 C10 H10 124.8 . . ? C10 C11 C12 107.13(15) . . ? C10 C11 C22 125.50(15) . . ? C12 C11 C22 127.27(15) . . ? C11 C12 H12 124.9 . . ? C11 C12 C13 110.10(15) . . ? C13 C12 H12 124.9 . . ? C12 C13 C9 106.58(14) . . ? C14 C13 C9 128.85(16) . . ? C14 C13 C12 124.57(16) . . ? C13 C14 C15 123.39(15) . . ? O3 C14 C13 122.04(16) . . ? O3 C14 C15 114.57(15) . . ? C16 C15 C14 121.87(15) . . ? C16 C15 C20 118.13(17) . . ? C20 C15 C14 119.91(16) . . ? C15 C16 H16 119.2 . . ? C17 C16 C15 121.61(16) . . ? C17 C16 H16 119.2 . . ? C16 C17 H17 120.3 . . ? C16 C17 C18 119.41(18) . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 119.90(18) . . ? O4 C18 C17 124.90(18) . . ? O4 C18 C19 115.20(17) . . ? C18 C19 H19 119.9 . . ? C20 C19 C18 120.20(17) . . ? C20 C19 H19 119.9 . . ? C15 C20 H20 119.6 . . ? C19 C20 C15 120.73(18) . . ? C19 C20 H20 119.6 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? C11 C22 C23 111.51(15) . . ? C11 C22 C24 108.18(15) . . ? C11 C22 C25 109.66(14) . . ? C23 C22 C24 109.66(17) . . ? C23 C22 C25 108.41(16) . . ? C25 C22 C24 109.40(16) . . ? 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 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C2 O1 C1 119.13(16) . . ? C8 O2 B1 123.85(15) . . ? C14 O3 B1 123.87(15) . . ? C18 O4 C21 118.57(17) . . ? 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 B1 F1 1.364(2) . ? B1 F2 1.370(3) . ? B1 O2 1.493(3) . ? B1 O3 1.489(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 O1 1.430(2) . ? C2 C3 1.391(2) . ? C2 C7 1.386(3) . ? C2 O1 1.354(2) . ? C3 H3 0.9300 . ? C3 C4 1.366(2) . ? C4 H4 0.9300 . ? C4 C5 1.399(2) . ? C5 C6 1.396(2) . ? C5 C8 1.461(2) . ? C6 H6 0.9300 . ? C6 C7 1.378(3) . ? C7 H7 0.9300 . ? C8 C9 1.401(2) . ? C8 O2 1.3086(19) . ? C9 C10 1.417(2) . ? C9 C13 1.456(2) . ? C10 H10 0.9300 . ? C10 C11 1.393(2) . ? C11 C12 1.395(2) . ? C11 C22 1.515(2) . ? C12 H12 0.9300 . ? C12 C13 1.411(2) . ? C13 C14 1.404(2) . ? C14 C15 1.455(2) . ? C14 O3 1.311(2) . ? C15 C16 1.392(2) . ? C15 C20 1.401(2) . ? C16 H16 0.9300 . ? C16 C17 1.377(3) . ? C17 H17 0.9300 . ? C17 C18 1.385(3) . ? C18 C19 1.397(3) . ? C18 O4 1.359(2) . ? C19 H19 0.9300 . ? C19 C20 1.367(3) . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C21 O4 1.425(3) . ? C22 C23 1.527(2) . ? C22 C24 1.533(3) . ? C22 C25 1.531(2) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 C2 C3 C4 C5 0.1(3) . . . . ? C3 C2 C7 C6 0.0(3) . . . . ? C3 C2 O1 C1 -175.17(18) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C3 C4 C5 C8 -176.64(17) . . . . ? C4 C5 C6 C7 0.8(3) . . . . ? C4 C5 C8 C9 -26.8(3) . . . . ? C4 C5 C8 O2 151.68(17) . . . . ? C5 C6 C7 C2 -0.5(3) . . . . ? C5 C8 C9 C10 -21.7(3) . . . . ? C5 C8 C9 C13 156.64(17) . . . . ? C5 C8 O2 B1 164.22(16) . . . . ? C6 C5 C8 C9 157.31(17) . . . . ? C6 C5 C8 O2 -24.2(2) . . . . ? C7 C2 C3 C4 0.2(3) . . . . ? C7 C2 O1 C1 3.2(3) . . . . ? C8 C5 C6 C7 176.92(17) . . . . ? C8 C9 C10 C11 -179.90(16) . . . . ? C8 C9 C13 C12 -178.41(17) . . . . ? C8 C9 C13 C14 1.0(3) . . . . ? C9 C8 O2 B1 -17.3(3) . . . . ? C9 C10 C11 C12 -2.57(19) . . . . ? C9 C10 C11 C22 174.04(16) . . . . ? C9 C13 C14 C15 -158.77(17) . . . . ? C9 C13 C14 O3 21.3(3) . . . . ? C10 C9 C13 C12 0.20(18) . . . . ? C10 C9 C13 C14 179.65(17) . . . . ? C10 C11 C12 C13 2.7(2) . . . . ? C10 C11 C22 C23 -179.58(18) . . . . ? C10 C11 C22 C24 -58.9(2) . . . . ? C10 C11 C22 C25 60.3(2) . . . . ? C11 C12 C13 C9 -1.8(2) . . . . ? C11 C12 C13 C14 178.73(16) . . . . ? C12 C11 C22 C23 -3.7(3) . . . . ? C12 C11 C22 C24 117.0(2) . . . . ? C12 C11 C22 C25 -123.74(19) . . . . ? C12 C13 C14 C15 20.6(3) . . . . ? C12 C13 C14 O3 -159.31(17) . . . . ? C13 C9 C10 C11 1.46(19) . . . . ? C13 C14 C15 C16 34.0(3) . . . . ? C13 C14 C15 C20 -149.66(18) . . . . ? C13 C14 O3 B1 15.6(3) . . . . ? C14 C15 C16 C17 176.89(17) . . . . ? C14 C15 C20 C19 -178.06(18) . . . . ? C15 C14 O3 B1 -164.34(16) . . . . ? C15 C16 C17 C18 0.6(3) . . . . ? C16 C15 C20 C19 -1.6(3) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C16 C17 C18 O4 -179.57(18) . . . . ? C17 C18 C19 C20 -0.6(3) . . . . ? C17 C18 O4 C21 -2.1(3) . . . . ? C18 C19 C20 C15 1.6(3) . . . . ? C19 C18 O4 C21 178.9(2) . . . . ? C20 C15 C16 C17 0.5(3) . . . . ? C22 C11 C12 C13 -173.84(16) . . . . ? F1 B1 O2 C8 -175.21(16) . . . . ? F1 B1 O3 C14 176.66(15) . . . . ? F2 B1 O2 C8 -52.1(2) . . . . ? F2 B1 O3 C14 53.8(2) . . . . ? O1 C2 C3 C4 178.68(17) . . . . ? O1 C2 C7 C6 -178.30(18) . . . . ? O2 B1 O3 C14 -68.3(2) . . . . ? O2 C8 C9 C10 159.97(17) . . . . ? O2 C8 C9 C13 -21.7(3) . . . . ? O3 B1 O2 C8 69.9(2) . . . . ? O3 C14 C15 C16 -146.11(17) . . . . ? O3 C14 C15 C20 30.2(2) . . . . ? O4 C18 C19 C20 178.58(19) . . . . ?