#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:12:07 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257326 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557869.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_1557869 loop_ _publ_author_name 'Yan, Chenting' 'Takeshita, Masato' 'Nakatsuji, Jun-ya' 'Kurosaki, Akihiro' 'Sato, Kaoko' 'Shang, Rong' 'Nakamoto, Masaaki' 'Yamamoto, Yohsuke' 'Adachi, Yohei' 'Furukawa, Ko' 'Kishi, Ryohei' 'Nakano, Masayoshi' _publ_section_title ; Synthesis and properties of hypervalent electron-rich pentacoordinate nitrogen compounds ; _journal_issue 19 _journal_name_full 'Chemical Science' _journal_page_first 5082 _journal_page_last 5088 _journal_paper_doi 10.1039/D0SC00002G _journal_volume 11 _journal_year 2020 _chemical_formula_sum 'C14 H17 Br O4' _chemical_formula_weight 329.18 _space_group_crystal_system orthorhombic _space_group_IT_number 60 _space_group_name_Hall '-P 2n 2ab' _space_group_name_H-M_alt 'P b c n' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-08-05 deposited with the CCDC. 2020-04-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 21.874(5) _cell_length_b 15.366(3) _cell_length_c 8.915(3) _cell_measurement_reflns_used 9936 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 2.65 _cell_volume 2996.5(14) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _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 0.0358 _diffrn_reflns_av_unetI/netI 0.0167 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 33840 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.343 _diffrn_reflns_theta_min 1.862 _exptl_absorpt_coefficient_mu 2.750 _exptl_absorpt_correction_T_max 0.458 _exptl_absorpt_correction_T_min 0.279 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1344 _exptl_crystal_size_max 0.596 _exptl_crystal_size_mid 0.433 _exptl_crystal_size_min 0.336 _refine_diff_density_max 0.630 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 177 _refine_ls_number_reflns 3737 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0272 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+1.7946P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.0727 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3279 _reflns_number_total 3737 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00002g2.cif _cod_data_source_block 1Me _cod_depositor_comments ;Adding full bibliography for 1557869--1557876.cif. Adding full bibliography for 1557869--1557876.cif. ; _cod_original_cell_volume 2996.4(12) _cod_database_code 1557869 _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 0.291 _shelx_estimated_absorpt_t_max 0.458 _shelx_res_file ; yan_exp421_0ma_a.res created by SHELXL-2014/7 TITL yan_exp421_0ma_a.res in Pbcn CELL 0.71073 21.8737 15.3665 8.9146 90.000 90.000 90.000 ZERR 8.00 0.0046 0.0027 0.0027 0.000 0.000 0.000 LATT 1 SYMM x+1/2, -y+1/2, -z SYMM -x, y, -z+1/2 SYMM -x+1/2, -y+1/2, z+1/2 SFAC C H O Br UNIT 112 136 32 8 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -100 SIZE 0.336 0.433 0.596 ACTA L.S. 20 FMAP 2 PLAN -4 0 0.00 HTAB BOND $H CONF WGHT 0.032700 1.794600 FVAR 0.33933 BR1 4 0.313556 0.682182 0.565276 11.00000 0.04286 0.03817 = 0.02650 0.00768 0.00308 -0.00694 O1 3 0.392111 0.548638 0.321757 11.00000 0.04023 0.02794 = 0.06616 0.00169 -0.02195 0.00411 O2 3 0.284022 0.879826 0.569540 11.00000 0.04018 0.05059 = 0.02743 -0.00802 0.00157 0.00303 O3 3 0.230968 0.897261 0.357908 11.00000 0.04299 0.06086 = 0.03638 -0.00568 -0.00303 0.01671 C3 1 0.417382 0.738990 0.188490 11.00000 0.02580 0.03045 = 0.02947 0.00165 0.00071 -0.00076 AFIX 43 H3 2 0.449669 0.711240 0.135647 11.00000 -1.20000 AFIX 0 O4 3 0.467074 0.613246 0.446460 11.00000 0.06345 0.04807 = 0.13782 0.03429 -0.06453 -0.01444 C4 1 0.394596 0.700505 0.317678 11.00000 0.02522 0.02868 = 0.03127 0.00516 -0.00585 -0.00417 C1 1 0.415053 0.463614 0.366964 11.00000 0.04747 0.03012 = 0.08588 0.01002 -0.01816 0.00571 AFIX 137 H1A 2 0.455146 0.453617 0.321027 11.00000 -1.50000 H1AB 2 0.386498 0.418379 0.333859 11.00000 -1.50000 H1AC 2 0.418953 0.461636 0.476426 11.00000 -1.50000 AFIX 0 C2 1 0.422387 0.616455 0.369574 11.00000 0.02719 0.03513 = 0.04029 0.01349 -0.00513 -0.00278 C6 1 0.274228 0.868613 0.423926 11.00000 0.03233 0.03170 = 0.02635 -0.00086 0.00227 -0.00434 C5 1 0.347776 0.740693 0.397877 11.00000 0.02862 0.03272 = 0.02231 0.00502 -0.00191 -0.00686 C7 1 0.234185 0.920940 0.650604 11.00000 0.05346 0.05730 = 0.03581 -0.01063 0.01186 0.00470 AFIX 137 H7A 2 0.228216 0.980224 0.612820 11.00000 -1.50000 H7AB 2 0.244103 0.923076 0.757745 11.00000 -1.50000 H7AC 2 0.196612 0.887259 0.635940 11.00000 -1.50000 AFIX 0 C8 1 0.324810 0.819808 0.348301 11.00000 0.02851 0.03047 = 0.02370 -0.00095 -0.00132 -0.00360 C10 1 0.394053 0.817500 0.134160 11.00000 0.02916 0.02856 = 0.02416 0.00196 -0.00145 -0.00472 C9 1 0.419287 0.855883 -0.011905 11.00000 0.03999 0.03340 = 0.02408 0.00421 0.00334 -0.00264 C11 1 0.387433 0.941247 -0.054030 11.00000 0.05290 0.05863 = 0.04481 0.02669 0.00977 0.01065 AFIX 137 H11A 2 0.404554 0.963385 -0.148178 11.00000 -1.50000 H11B 2 0.393834 0.984166 0.025752 11.00000 -1.50000 H11C 2 0.343534 0.930794 -0.066610 11.00000 -1.50000 AFIX 0 C12 1 0.487494 0.874947 0.007728 11.00000 0.04194 0.04951 = 0.04987 0.01483 0.01045 -0.00455 AFIX 137 H12A 2 0.509453 0.820405 0.026241 11.00000 -1.50000 H12B 2 0.493307 0.914294 0.093060 11.00000 -1.50000 H12C 2 0.503398 0.902351 -0.083547 11.00000 -1.50000 AFIX 0 C15 1 0.347627 0.856543 0.216263 11.00000 0.03047 0.02673 = 0.02616 0.00207 -0.00245 -0.00082 AFIX 43 H15 2 0.330839 0.909900 0.181617 11.00000 -1.20000 AFIX 0 C14 1 0.410223 0.789572 -0.137752 11.00000 0.11524 0.06103 = 0.02717 -0.00668 0.01116 -0.03307 AFIX 137 H14A 2 0.366705 0.775263 -0.146406 11.00000 -1.50000 H14B 2 0.433430 0.736655 -0.114892 11.00000 -1.50000 H14C 2 0.424723 0.814280 -0.232648 11.00000 -1.50000 REM REM C:\frames\guest\20180917_yan_exp421\work\autostructure_private\yan_exp42 REM 1_0ma_a.hkl REM AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM yan_exp421_0ma_a.res in Pbcn REM R1 = 0.0272 for 3279 Fo > 4sig(Fo) and 0.0325 for all 3737 data REM 177 parameters refined using 0 restraints END WGHT 0.0327 1.7946 REM Instructions for potential hydrogen bonds EQIV $1 -x+1/2, y-1/2, z HTAB C1 O3_$1 REM Highest difference peak 0.630, deepest hole -0.507, 1-sigma level 0.053 Q1 1 0.4774 0.5942 0.3551 11.00000 0.05 0.63 Q2 1 0.4429 0.6011 0.4771 11.00000 0.05 0.41 Q3 1 0.2224 0.8482 0.3867 11.00000 0.05 0.33 Q4 1 0.4060 0.6618 0.3382 11.00000 0.05 0.32 ; _shelx_res_checksum 71017 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' '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 0.31356(2) 0.68218(2) 0.56528(2) 0.03584(7) Uani 1 1 d . . . . . O1 O 0.39211(6) 0.54864(8) 0.32176(18) 0.0448(3) Uani 1 1 d . . . . . O2 O 0.28402(6) 0.87983(9) 0.56954(13) 0.0394(3) Uani 1 1 d . . . . . O3 O 0.23097(6) 0.89726(10) 0.35791(16) 0.0467(3) Uani 1 1 d . . . . . C3 C 0.41738(7) 0.73899(11) 0.18849(18) 0.0286(3) Uani 1 1 d . . . . . H3 H 0.4497 0.7112 0.1356 0.034 Uiso 1 1 calc R U . . . O4 O 0.46707(9) 0.61325(11) 0.4465(3) 0.0831(7) Uani 1 1 d . . . . . C4 C 0.39460(7) 0.70051(11) 0.31768(19) 0.0284(3) Uani 1 1 d . . . . . C1 C 0.41505(10) 0.46361(13) 0.3670(3) 0.0545(6) Uani 1 1 d . . . . . H1A H 0.4551 0.4536 0.3210 0.082 Uiso 1 1 calc R U . . . H1AB H 0.3865 0.4184 0.3339 0.082 Uiso 1 1 calc R U . . . H1AC H 0.4190 0.4616 0.4764 0.082 Uiso 1 1 calc R U . . . C2 C 0.42239(8) 0.61646(12) 0.3696(2) 0.0342(4) Uani 1 1 d . . . . . C6 C 0.27423(8) 0.86861(11) 0.42393(18) 0.0301(3) Uani 1 1 d . . . . . C5 C 0.34778(7) 0.74069(11) 0.39788(18) 0.0279(3) Uani 1 1 d . . . . . C7 C 0.23419(10) 0.92094(15) 0.6506(2) 0.0489(5) Uani 1 1 d . . . . . H7A H 0.2282 0.9802 0.6128 0.073 Uiso 1 1 calc R U . . . H7AB H 0.2441 0.9231 0.7577 0.073 Uiso 1 1 calc R U . . . H7AC H 0.1966 0.8873 0.6359 0.073 Uiso 1 1 calc R U . . . C8 C 0.32481(8) 0.81981(10) 0.34830(19) 0.0276(3) Uani 1 1 d . . . . . C10 C 0.39405(7) 0.81750(10) 0.13416(18) 0.0273(3) Uani 1 1 d . . . . . C9 C 0.41929(8) 0.85588(11) -0.01190(19) 0.0325(3) Uani 1 1 d . . . . . C11 C 0.38743(11) 0.94125(16) -0.0540(2) 0.0521(6) Uani 1 1 d . . . . . H11A H 0.4046 0.9634 -0.1482 0.078 Uiso 1 1 calc R U . . . H11B H 0.3938 0.9842 0.0258 0.078 Uiso 1 1 calc R U . . . H11C H 0.3435 0.9308 -0.0666 0.078 Uiso 1 1 calc R U . . . C12 C 0.48749(9) 0.87495(14) 0.0077(3) 0.0471(5) Uani 1 1 d . . . . . H12A H 0.5095 0.8204 0.0262 0.071 Uiso 1 1 calc R U . . . H12B H 0.4933 0.9143 0.0931 0.071 Uiso 1 1 calc R U . . . H12C H 0.5034 0.9024 -0.0835 0.071 Uiso 1 1 calc R U . . . C15 C 0.34763(7) 0.85654(10) 0.21626(18) 0.0278(3) Uani 1 1 d . . . . . H15 H 0.3308 0.9099 0.1816 0.033 Uiso 1 1 calc R U . . . C14 C 0.41022(16) 0.78957(17) -0.1378(2) 0.0678(8) Uani 1 1 d . . . . . H14A H 0.3667 0.7753 -0.1464 0.102 Uiso 1 1 calc R U . . . H14B H 0.4334 0.7367 -0.1149 0.102 Uiso 1 1 calc R U . . . H14C H 0.4247 0.8143 -0.2326 0.102 Uiso 1 1 calc R U . . . 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 0.04286(12) 0.03817(11) 0.02650(10) 0.00768(6) 0.00308(7) -0.00694(7) O1 0.0402(7) 0.0279(6) 0.0662(9) 0.0017(6) -0.0220(7) 0.0041(5) O2 0.0402(7) 0.0506(8) 0.0274(6) -0.0080(5) 0.0016(5) 0.0030(6) O3 0.0430(7) 0.0609(9) 0.0364(7) -0.0057(6) -0.0030(6) 0.0167(7) C3 0.0258(7) 0.0305(8) 0.0295(8) 0.0017(6) 0.0007(6) -0.0008(6) O4 0.0634(11) 0.0481(9) 0.1378(19) 0.0343(10) -0.0645(12) -0.0144(8) C4 0.0252(7) 0.0287(7) 0.0313(8) 0.0052(6) -0.0059(6) -0.0042(6) C1 0.0475(11) 0.0301(9) 0.0859(17) 0.0100(10) -0.0182(12) 0.0057(8) C2 0.0272(8) 0.0351(9) 0.0403(9) 0.0135(7) -0.0051(7) -0.0028(7) C6 0.0323(8) 0.0317(8) 0.0264(8) -0.0009(6) 0.0023(6) -0.0043(6) C5 0.0286(7) 0.0327(8) 0.0223(7) 0.0050(6) -0.0019(6) -0.0069(6) C7 0.0535(12) 0.0573(13) 0.0358(10) -0.0106(9) 0.0119(9) 0.0047(10) C8 0.0285(7) 0.0305(8) 0.0237(7) -0.0009(6) -0.0013(6) -0.0036(6) C10 0.0292(8) 0.0286(8) 0.0242(7) 0.0020(6) -0.0015(6) -0.0047(6) C9 0.0400(9) 0.0334(8) 0.0241(7) 0.0042(6) 0.0033(7) -0.0026(7) C11 0.0529(12) 0.0586(13) 0.0448(11) 0.0267(10) 0.0098(9) 0.0106(10) C12 0.0419(11) 0.0495(11) 0.0499(11) 0.0148(10) 0.0105(9) -0.0045(9) C15 0.0305(8) 0.0267(7) 0.0262(7) 0.0021(6) -0.0024(6) -0.0008(6) C14 0.115(2) 0.0610(14) 0.0272(10) -0.0067(10) 0.0112(12) -0.0331(15) 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' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 116.79(14) . . ? C6 O2 C7 114.96(15) . . ? C4 C3 C10 121.66(15) . . ? C4 C3 H3 119.2 . . ? C10 C3 H3 119.2 . . ? C3 C4 C5 120.07(15) . . ? C3 C4 C2 118.51(15) . . ? C5 C4 C2 121.40(15) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1AB 109.5 . . ? H1A C1 H1AB 109.5 . . ? O1 C1 H1AC 109.5 . . ? H1A C1 H1AC 109.5 . . ? H1AB C1 H1AC 109.5 . . ? O4 C2 O1 124.68(17) . . ? O4 C2 C4 122.94(17) . . ? O1 C2 C4 112.38(14) . . ? O3 C6 O2 124.08(16) . . ? O3 C6 C8 123.13(15) . . ? O2 C6 C8 112.72(15) . . ? C8 C5 C4 119.40(15) . . ? C8 C5 Br1 121.54(13) . . ? C4 C5 Br1 118.93(12) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7AB 109.5 . . ? H7A C7 H7AB 109.5 . . ? O2 C7 H7AC 109.5 . . ? H7A C7 H7AC 109.5 . . ? H7AB C7 H7AC 109.5 . . ? C5 C8 C15 119.53(15) . . ? C5 C8 C6 124.27(15) . . ? C15 C8 C6 116.16(14) . . ? C15 C10 C3 117.25(15) . . ? C15 C10 C9 123.04(14) . . ? C3 C10 C9 119.71(15) . . ? C14 C9 C12 109.75(19) . . ? C14 C9 C11 109.38(19) . . ? C12 C9 C11 107.91(16) . . ? C14 C9 C10 108.69(15) . . ? C12 C9 C10 109.13(15) . . ? C11 C9 C10 111.97(15) . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C15 C8 122.06(15) . . ? C10 C15 H15 119.0 . . ? C8 C15 H15 119.0 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C5 1.8962(16) . ? O1 C2 1.306(2) . ? O1 C1 1.456(2) . ? O2 C6 1.327(2) . ? O2 C7 1.452(2) . ? O3 C6 1.198(2) . ? C3 C4 1.387(2) . ? C3 C10 1.397(2) . ? C3 H3 0.9500 . ? O4 C2 1.195(2) . ? C4 C5 1.393(2) . ? C4 C2 1.501(2) . ? C1 H1A 0.9800 . ? C1 H1AB 0.9800 . ? C1 H1AC 0.9800 . ? C6 C8 1.497(2) . ? C5 C8 1.388(2) . ? C7 H7A 0.9800 . ? C7 H7AB 0.9800 . ? C7 H7AC 0.9800 . ? C8 C15 1.398(2) . ? C10 C15 1.388(2) . ? C10 C9 1.532(2) . ? C9 C14 1.528(3) . ? C9 C12 1.530(3) . ? C9 C11 1.532(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C15 H15 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C10 C3 C4 C5 -0.8(2) . . . . ? C10 C3 C4 C2 -179.54(15) . . . . ? C1 O1 C2 O4 0.2(3) . . . . ? C1 O1 C2 C4 -179.51(18) . . . . ? C3 C4 C2 O4 85.4(3) . . . . ? C5 C4 C2 O4 -93.4(3) . . . . ? C3 C4 C2 O1 -94.91(19) . . . . ? C5 C4 C2 O1 86.4(2) . . . . ? C7 O2 C6 O3 7.4(3) . . . . ? C7 O2 C6 C8 -175.49(16) . . . . ? C3 C4 C5 C8 -0.8(2) . . . . ? C2 C4 C5 C8 177.92(15) . . . . ? C3 C4 C5 Br1 175.33(12) . . . . ? C2 C4 C5 Br1 -6.0(2) . . . . ? C4 C5 C8 C15 2.0(2) . . . . ? Br1 C5 C8 C15 -173.99(12) . . . . ? C4 C5 C8 C6 179.32(15) . . . . ? Br1 C5 C8 C6 3.3(2) . . . . ? O3 C6 C8 C5 -131.27(19) . . . . ? O2 C6 C8 C5 51.6(2) . . . . ? O3 C6 C8 C15 46.1(2) . . . . ? O2 C6 C8 C15 -131.04(16) . . . . ? C4 C3 C10 C15 1.1(2) . . . . ? C4 C3 C10 C9 -177.96(15) . . . . ? C15 C10 C9 C14 -120.7(2) . . . . ? C3 C10 C9 C14 58.3(2) . . . . ? C15 C10 C9 C12 119.62(18) . . . . ? C3 C10 C9 C12 -61.4(2) . . . . ? C15 C10 C9 C11 0.2(2) . . . . ? C3 C10 C9 C11 179.21(17) . . . . ? C3 C10 C15 C8 0.2(2) . . . . ? C9 C10 C15 C8 179.22(15) . . . . ? C5 C8 C15 C10 -1.8(2) . . . . ? C6 C8 C15 C10 -179.28(15) . . . . ?