#------------------------------------------------------------------------------ #$Date: 2016-05-12 06:04:22 +0300 (Thu, 12 May 2016) $ #$Revision: 182890 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225202.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_7225202 loop_ _publ_author_name 'Veerakanellore, Giri Babu' 'Captain, Burjor' 'Ramamurthy, Vaidhyanathan' _publ_section_title ; Solid-state photochemistry of cis-cinnamic acids: A competition between [2+2] addition and cis-trans isomerization ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C6CE00682E _journal_year 2016 _chemical_formula_sum 'C22 H26 Br2 O9' _chemical_formula_weight 594.25 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-03-10 deposited with the CCDC. 2016-05-11 downloaded from the CCDC. ; _cell_angle_alpha 108.1410(10) _cell_angle_beta 102.7940(10) _cell_angle_gamma 94.1940(10) _cell_formula_units_Z 2 _cell_length_a 9.0513(5) _cell_length_b 10.3906(5) _cell_length_c 14.5614(7) _cell_measurement_reflns_used 6033 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.93 _cell_measurement_theta_min 2.34 _cell_volume 1254.09(11) _computing_cell_refinement 'SAINT+ V8.34A (Bruker, 2015)' _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_data_reduction 'SAINT+ V8.34A (Bruker, 2015)' _computing_molecular_graphics 'XSHELL v6.3.1 (Bruker, 2004)' _computing_publication_material 'XCIF v2014/2 (Bruker, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS/SHELXTL V6.14 (Bruker, 2015)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_unetI/netI 0.0300 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 17137 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.997 _diffrn_reflns_theta_min 1.523 _exptl_absorpt_coefficient_mu 3.279 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.4641 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS 2014/5 Bruker)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.574 _exptl_crystal_description block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.360 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.767 _refine_diff_density_min -0.992 _refine_diff_density_rms 0.091 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 318 _refine_ls_number_reflns 6049 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0482 _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^)+(0.0634P)^2^+1.2012P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1227 _refine_ls_wR_factor_ref 0.1317 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4618 _reflns_number_total 6049 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00682e2.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas ; _cod_database_code 7225202 _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 0.385 _shelx_estimated_absorpt_t_max 0.779 _shelx_res_file ; collect_0m.res created by SHELXL-2014/7 TITL collect_0m in P-1 CELL 0.71073 9.0513 10.3906 14.5614 108.141 102.794 94.194 ZERR 2.00 0.0005 0.0005 0.0007 0.001 0.001 0.001 LATT 1 SFAC C H O Br UNIT 44 52 18 4 OMIT -3 56 L.S. 4 ACTA BOND FMAP 2 PLAN 5 SIZE 0.080 0.300 0.360 FREE C22 C21 TEMP 23.000 WGHT 0.063400 1.201200 FVAR 0.17707 BR1 4 0.844088 1.062071 1.187367 11.00000 0.04879 0.09740 = 0.03517 0.00943 0.01254 0.00463 BR2 4 0.337246 0.689701 1.019763 11.00000 0.12772 0.08074 = 0.09220 0.05188 0.07461 0.03334 O1 3 0.733010 0.919623 0.611334 11.00000 0.11437 0.05048 = 0.03862 0.01028 0.03254 -0.01325 O2 3 0.812927 1.133968 0.710993 11.00000 0.07176 0.04257 = 0.04450 0.02241 0.01420 -0.00775 AFIX 147 H2 2 0.833750 1.142478 0.660969 11.00000 -1.50000 AFIX 0 O3 3 0.860614 0.616506 0.812227 11.00000 0.07152 0.04343 = 0.04708 0.01920 0.00799 0.01665 O4 3 0.332803 0.857363 0.614222 11.00000 0.06243 0.04131 = 0.04440 0.01001 -0.00835 0.01053 O5 3 0.422190 1.078689 0.693369 11.00000 0.05851 0.03599 = 0.06450 0.02401 -0.00567 0.00615 AFIX 147 H5 2 0.343524 1.088328 0.657131 11.00000 -1.50000 AFIX 0 O6 3 0.539884 0.499095 0.638957 11.00000 0.08628 0.03239 = 0.05621 0.00253 0.02527 0.00211 C1 1 0.810701 0.834921 0.891874 11.00000 0.02952 0.04235 = 0.03296 0.01769 0.00483 0.00012 C2 1 0.858548 0.712081 0.900043 11.00000 0.04102 0.04841 = 0.04313 0.02310 0.00382 0.00598 C3 1 0.898252 0.694741 0.992362 11.00000 0.06536 0.06240 = 0.05172 0.03362 0.00246 0.01493 AFIX 43 H3 2 0.928758 0.612853 0.996774 11.00000 -1.20000 AFIX 0 C4 1 0.893018 0.797655 1.077821 11.00000 0.05555 0.07981 = 0.04061 0.03410 -0.00052 0.00441 AFIX 43 H4 2 0.918796 0.785407 1.139690 11.00000 -1.20000 AFIX 0 C5 1 0.849408 0.917992 1.070382 11.00000 0.03267 0.06317 = 0.03206 0.01663 0.00536 -0.00119 C6 1 0.807785 0.937575 0.978298 11.00000 0.03214 0.04940 = 0.03476 0.01684 0.00737 0.00142 AFIX 43 H6 2 0.777909 1.020125 0.975013 11.00000 -1.20000 AFIX 0 C7 1 0.755628 0.840897 0.788285 11.00000 0.03469 0.03364 = 0.03027 0.01353 0.00782 0.00365 AFIX 13 H7 2 0.822478 0.802341 0.745574 11.00000 -1.20000 AFIX 0 C8 1 0.715028 0.980597 0.779940 11.00000 0.04092 0.03263 = 0.02657 0.01108 0.00557 -0.00070 AFIX 13 H8 2 0.753586 1.057655 0.842708 11.00000 -1.20000 AFIX 0 C9 1 0.754557 1.007076 0.691834 11.00000 0.04258 0.03938 = 0.03407 0.01767 0.00960 0.00032 C10 1 0.897542 0.486105 0.813265 11.00000 0.13663 0.05068 = 0.07314 0.02681 0.02376 0.03695 AFIX 137 H10A 2 1.000641 0.496882 0.852818 11.00000 -1.50000 H10B 2 0.888826 0.427410 0.746120 11.00000 -1.50000 H10C 2 0.828073 0.446042 0.841556 11.00000 -1.50000 AFIX 0 C11 1 0.506503 0.676471 0.775026 11.00000 0.03374 0.02950 = 0.03579 0.01316 0.00276 0.00172 C12 1 0.489996 0.535031 0.724761 11.00000 0.05141 0.03131 = 0.04874 0.01024 0.01198 0.00203 C13 1 0.429328 0.442351 0.762037 11.00000 0.08016 0.02976 = 0.08665 0.01903 0.02685 0.00092 AFIX 43 H13 2 0.420192 0.348873 0.728261 11.00000 -1.20000 AFIX 0 C14 1 0.382204 0.486993 0.848764 11.00000 0.07963 0.04514 = 0.08701 0.03821 0.03701 0.00467 AFIX 43 H14 2 0.341008 0.424273 0.873570 11.00000 -1.20000 AFIX 0 C15 1 0.396677 0.624606 0.897995 11.00000 0.05314 0.04973 = 0.05803 0.02839 0.02304 0.01065 C16 1 0.458542 0.719199 0.862017 11.00000 0.04351 0.03228 = 0.04236 0.01676 0.01191 0.00580 AFIX 43 H16 2 0.467862 0.812387 0.896792 11.00000 -1.20000 AFIX 0 C17 1 0.581333 0.776247 0.737360 11.00000 0.03689 0.02826 = 0.02601 0.00947 0.00441 0.00165 AFIX 13 H17 2 0.567602 0.734169 0.665139 11.00000 -1.20000 AFIX 0 C18 1 0.542763 0.922285 0.759523 11.00000 0.03673 0.02914 = 0.02913 0.01295 0.00751 0.00428 AFIX 13 H18 2 0.512738 0.949742 0.822708 11.00000 -1.20000 AFIX 0 C19 1 0.422732 0.948001 0.680711 11.00000 0.04050 0.03711 = 0.03187 0.01628 0.01013 0.00734 C20 1 0.529140 0.356853 0.584470 11.00000 0.10659 0.04024 = 0.08351 -0.00617 0.03606 0.00555 AFIX 137 H20A 2 0.587797 0.313678 0.626609 11.00000 -1.50000 H20B 2 0.568617 0.346677 0.527017 11.00000 -1.50000 H20C 2 0.423780 0.314551 0.563145 11.00000 -1.50000 AFIX 0 C21 1 1.082336 0.536610 0.593304 11.00000 0.18067 0.19324 = 0.15708 0.11834 -0.09103 -0.09985 AFIX 23 H21A 2 1.155860 0.531309 0.651126 11.00000 -1.20000 H21B 2 1.062647 0.629983 0.603967 11.00000 -1.20000 AFIX 0 C22 1 0.872632 0.530998 0.509503 11.00000 0.22891 0.44530 = 0.50540 0.37510 0.27034 0.25117 AFIX 23 H22A 2 0.908611 0.628815 0.538598 11.00000 -1.20000 H22B 2 0.763338 0.512820 0.502541 11.00000 -1.20000 AFIX 0 H31 2 0.198678 0.104986 0.511606 11.00000 0.07326 H32 2 0.107900 0.128949 0.560120 11.00000 0.07223 H33 2 0.920927 0.255850 0.563327 11.00000 0.07275 H34 2 0.830732 0.149657 0.508422 11.00000 0.09783 O11 3 0.195836 0.122280 0.567217 11.00000 0.05880 0.09418 = 0.04546 0.03367 0.01714 0.03248 O12 3 0.894976 0.191953 0.561891 11.00000 0.05154 0.05006 = 0.04600 0.02489 0.00629 -0.00175 O13 3 0.962323 0.451141 0.566269 11.00000 0.34440 0.11754 = 0.13132 0.08328 0.02961 -0.05858 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM collect_0m in P-1 REM R1 = 0.0482 for 4618 Fo > 4sig(Fo) and 0.0649 for all 6049 data REM 318 parameters refined using 0 restraints END WGHT 0.0634 1.2013 REM Highest difference peak 0.767, deepest hole -0.992, 1-sigma level 0.091 Q1 1 0.9178 0.5874 0.4536 11.00000 0.05 0.77 Q2 1 0.3518 0.6091 0.9879 11.00000 0.05 0.70 Q3 1 0.2574 0.6890 0.9656 11.00000 0.05 0.63 Q4 1 0.8526 0.4634 0.4656 11.00000 0.05 0.58 Q5 1 0.9433 0.5643 0.5746 11.00000 0.05 0.55 ; _shelx_res_checksum 47373 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 Br1 Br 0.84409(4) 1.06207(5) 1.18737(2) 0.06362(15) Uani 1 1 d . . Br2 Br 0.33725(7) 0.68970(5) 1.01976(4) 0.08609(19) Uani 1 1 d . . O1 O 0.7330(4) 0.9196(3) 0.61133(18) 0.0682(8) Uani 1 1 d . . O2 O 0.8129(3) 1.1340(2) 0.71099(17) 0.0521(6) Uani 1 1 d . . H2 H 0.8338 1.1425 0.6610 0.078 Uiso 1 1 calc R U O3 O 0.8606(3) 0.6165(2) 0.81223(17) 0.0539(6) Uani 1 1 d . . O4 O 0.3328(3) 0.8574(2) 0.61422(17) 0.0540(6) Uani 1 1 d . . O5 O 0.4222(3) 1.0787(2) 0.69337(19) 0.0549(6) Uani 1 1 d . . H5 H 0.3435 1.0883 0.6571 0.082 Uiso 1 1 calc R U O6 O 0.5399(3) 0.4991(2) 0.63896(19) 0.0605(7) Uani 1 1 d . . C1 C 0.8107(3) 0.8349(3) 0.8919(2) 0.0346(6) Uani 1 1 d . . C2 C 0.8585(3) 0.7121(3) 0.9000(2) 0.0436(7) Uani 1 1 d . . C3 C 0.8983(4) 0.6947(4) 0.9924(3) 0.0582(9) Uani 1 1 d . . H3 H 0.9288 0.6129 0.9968 0.070 Uiso 1 1 calc R U C4 C 0.8930(4) 0.7977(4) 1.0778(3) 0.0578(9) Uani 1 1 d . . H4 H 0.9188 0.7854 1.1397 0.069 Uiso 1 1 calc R U C5 C 0.8494(3) 0.9180(4) 1.0704(2) 0.0434(7) Uani 1 1 d . . C6 C 0.8078(3) 0.9376(3) 0.9783(2) 0.0386(6) Uani 1 1 d . . H6 H 0.7779 1.0201 0.9750 0.046 Uiso 1 1 calc R U C7 C 0.7556(3) 0.8409(3) 0.78829(19) 0.0324(5) Uani 1 1 d . . H7 H 0.8225 0.8023 0.7456 0.039 Uiso 1 1 calc R U C8 C 0.7150(3) 0.9806(3) 0.77994(19) 0.0340(6) Uani 1 1 d . . H8 H 0.7536 1.0577 0.8427 0.041 Uiso 1 1 calc R U C9 C 0.7546(3) 1.0071(3) 0.6918(2) 0.0378(6) Uani 1 1 d . . C10 C 0.8975(7) 0.4861(4) 0.8133(4) 0.0847(15) Uani 1 1 d . . H10A H 1.0006 0.4969 0.8528 0.127 Uiso 1 1 calc R U H10B H 0.8888 0.4274 0.7461 0.127 Uiso 1 1 calc R U H10C H 0.8281 0.4460 0.8416 0.127 Uiso 1 1 calc R U C11 C 0.5065(3) 0.6765(3) 0.7750(2) 0.0337(5) Uani 1 1 d . . C12 C 0.4900(4) 0.5350(3) 0.7248(2) 0.0450(7) Uani 1 1 d . . C13 C 0.4293(5) 0.4424(4) 0.7620(3) 0.0652(10) Uani 1 1 d . . H13 H 0.4202 0.3489 0.7283 0.078 Uiso 1 1 calc R U C14 C 0.3822(5) 0.4870(4) 0.8488(3) 0.0644(10) Uani 1 1 d . . H14 H 0.3410 0.4243 0.8736 0.077 Uiso 1 1 calc R U C15 C 0.3967(4) 0.6246(3) 0.8980(3) 0.0496(8) Uani 1 1 d . . C16 C 0.4585(3) 0.7192(3) 0.8620(2) 0.0382(6) Uani 1 1 d . . H16 H 0.4679 0.8124 0.8968 0.046 Uiso 1 1 calc R U C17 C 0.5813(3) 0.7762(3) 0.73736(19) 0.0311(5) Uani 1 1 d . . H17 H 0.5676 0.7342 0.6651 0.037 Uiso 1 1 calc R U C18 C 0.5428(3) 0.9223(3) 0.75952(19) 0.0311(5) Uani 1 1 d . . H18 H 0.5127 0.9497 0.8227 0.037 Uiso 1 1 calc R U C19 C 0.4227(3) 0.9480(3) 0.6807(2) 0.0352(6) Uani 1 1 d . . C20 C 0.5291(6) 0.3569(4) 0.5845(4) 0.0817(14) Uani 1 1 d . . H20A H 0.5878 0.3137 0.6266 0.122 Uiso 1 1 calc R U H20B H 0.5686 0.3467 0.5270 0.122 Uiso 1 1 calc R U H20C H 0.4238 0.3146 0.5631 0.122 Uiso 1 1 calc R U C21 C 1.0823(12) 0.5366(11) 0.5933(7) 0.192(6) Uani 1 1 d . . H21A H 1.1559 0.5313 0.6511 0.230 Uiso 1 1 calc R U H21B H 1.0626 0.6300 0.6040 0.230 Uiso 1 1 calc R U C22 C 0.8726(15) 0.5310(18) 0.5095(15) 0.301(11) Uani 1 1 d . . H22A H 0.9086 0.6288 0.5386 0.362 Uiso 1 1 calc R U H22B H 0.7633 0.5128 0.5025 0.362 Uiso 1 1 calc R U H31 H 0.199(5) 0.105(5) 0.512(4) 0.073(15) Uiso 1 1 d . . H32 H 0.108(6) 0.129(5) 0.560(4) 0.072(15) Uiso 1 1 d . . H33 H 0.921(6) 0.256(5) 0.563(4) 0.073(17) Uiso 1 1 d . . H34 H 0.831(7) 0.150(6) 0.508(4) 0.098(18) Uiso 1 1 d . . O11 O 0.1958(4) 0.1223(3) 0.5672(2) 0.0620(7) Uani 1 1 d . . O12 O 0.8950(3) 0.1920(3) 0.5619(2) 0.0487(6) Uani 1 1 d . . O13 O 0.9623(11) 0.4511(6) 0.5663(4) 0.198(3) 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 0.0488(2) 0.0974(3) 0.03517(18) 0.00943(17) 0.01254(14) 0.00463(18) Br2 0.1277(4) 0.0807(3) 0.0922(3) 0.0519(3) 0.0746(3) 0.0333(3) O1 0.114(2) 0.0505(14) 0.0386(12) 0.0103(11) 0.0325(14) -0.0133(14) O2 0.0718(15) 0.0426(12) 0.0445(12) 0.0224(10) 0.0142(11) -0.0078(11) O3 0.0715(16) 0.0434(12) 0.0471(13) 0.0192(10) 0.0080(11) 0.0167(11) O4 0.0624(14) 0.0413(12) 0.0444(12) 0.0100(10) -0.0083(11) 0.0105(10) O5 0.0585(14) 0.0360(12) 0.0645(15) 0.0240(11) -0.0057(11) 0.0061(10) O6 0.0863(18) 0.0324(11) 0.0562(14) 0.0025(10) 0.0253(13) 0.0021(11) C1 0.0295(12) 0.0424(15) 0.0330(13) 0.0177(11) 0.0048(10) 0.0001(11) C2 0.0410(15) 0.0484(17) 0.0431(16) 0.0231(14) 0.0038(12) 0.0060(13) C3 0.065(2) 0.062(2) 0.052(2) 0.0336(18) 0.0025(17) 0.0149(18) C4 0.056(2) 0.080(3) 0.0406(17) 0.0341(18) -0.0005(15) 0.0044(18) C5 0.0327(14) 0.063(2) 0.0321(14) 0.0166(13) 0.0054(11) -0.0012(13) C6 0.0321(13) 0.0494(17) 0.0348(14) 0.0168(12) 0.0074(11) 0.0014(12) C7 0.0347(13) 0.0336(13) 0.0303(12) 0.0135(10) 0.0078(10) 0.0037(10) C8 0.0409(14) 0.0326(13) 0.0266(12) 0.0111(10) 0.0056(10) -0.0007(11) C9 0.0426(15) 0.0394(15) 0.0341(14) 0.0177(12) 0.0096(11) 0.0003(12) C10 0.137(4) 0.051(2) 0.073(3) 0.027(2) 0.024(3) 0.037(3) C11 0.0337(13) 0.0295(13) 0.0358(13) 0.0132(11) 0.0028(11) 0.0017(10) C12 0.0514(17) 0.0313(14) 0.0487(17) 0.0102(13) 0.0120(14) 0.0020(13) C13 0.080(3) 0.0298(16) 0.087(3) 0.0190(17) 0.027(2) 0.0009(16) C14 0.080(3) 0.045(2) 0.087(3) 0.0382(19) 0.037(2) 0.0047(18) C15 0.0531(19) 0.0497(19) 0.058(2) 0.0284(16) 0.0230(16) 0.0107(15) C16 0.0435(15) 0.0323(14) 0.0424(15) 0.0168(12) 0.0119(12) 0.0058(12) C17 0.0369(13) 0.0283(12) 0.0260(11) 0.0095(10) 0.0044(10) 0.0016(10) C18 0.0367(13) 0.0291(12) 0.0291(12) 0.0129(10) 0.0075(10) 0.0043(10) C19 0.0405(14) 0.0371(14) 0.0319(13) 0.0163(11) 0.0101(11) 0.0073(11) C20 0.107(4) 0.040(2) 0.084(3) -0.006(2) 0.036(3) 0.006(2) C21 0.181(9) 0.193(9) 0.157(8) 0.118(8) -0.091(7) -0.100(8) C22 0.229(13) 0.45(2) 0.51(3) 0.38(2) 0.270(17) 0.251(16) O11 0.0588(17) 0.094(2) 0.0455(14) 0.0337(14) 0.0171(12) 0.0325(15) O12 0.0515(14) 0.0501(15) 0.0460(13) 0.0249(12) 0.0063(11) -0.0017(11) O13 0.344(10) 0.118(4) 0.131(4) 0.083(4) 0.030(5) -0.059(5) 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_3 C2 O3 C10 118.4(3) . C12 O6 C20 118.3(3) . C6 C1 C2 118.2(3) . C6 C1 C7 124.5(3) . C2 C1 C7 117.2(3) . O3 C2 C3 124.6(3) . O3 C2 C1 115.0(3) . C3 C2 C1 120.4(3) . C4 C3 C2 120.6(3) . C5 C4 C3 119.1(3) . C4 C5 C6 121.4(3) . C4 C5 Br1 119.8(2) . C6 C5 Br1 118.8(3) . C1 C6 C5 120.2(3) . C1 C7 C8 116.9(2) . C1 C7 C17 113.2(2) . C8 C7 C17 88.81(19) . C9 C8 C7 112.3(2) . C9 C8 C18 113.4(2) . C7 C8 C18 88.21(19) . O1 C9 O2 123.5(3) . O1 C9 C8 123.1(3) . O2 C9 C8 113.4(2) . C16 C11 C12 117.8(3) . C16 C11 C17 121.8(2) . C12 C11 C17 120.3(3) . O6 C12 C13 124.3(3) . O6 C12 C11 115.0(3) . C13 C12 C11 120.7(3) . C14 C13 C12 120.6(3) . C15 C14 C13 119.2(3) . C14 C15 C16 121.0(3) . C14 C15 Br2 120.3(3) . C16 C15 Br2 118.7(2) . C11 C16 C15 120.7(3) . C11 C17 C18 120.7(2) . C11 C17 C7 119.3(2) . C18 C17 C7 88.19(19) . C19 C18 C17 117.1(2) . C19 C18 C8 120.8(2) . C17 C18 C8 90.6(2) . O4 C19 O5 123.6(3) . O4 C19 C18 123.1(3) . O5 C19 C18 113.3(2) . O13 C21 C22 92.4(9) 2_766 O13 C22 C21 96.4(8) 2_766 C21 O13 C22 92.6(8) . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br1 C5 1.898(3) . Br2 C15 1.903(3) . O1 C9 1.203(4) . O2 C9 1.304(4) . O3 C2 1.358(4) . O3 C10 1.423(4) . O4 C19 1.207(4) . O5 C19 1.313(3) . O6 C12 1.374(4) . O6 C20 1.428(4) . C1 C6 1.380(4) . C1 C2 1.408(4) . C1 C7 1.502(4) . C2 C3 1.384(4) . C3 C4 1.378(6) . C4 C5 1.367(5) . C5 C6 1.392(4) . C7 C8 1.557(4) . C7 C17 1.583(4) . C8 C9 1.503(4) . C8 C18 1.559(4) . C11 C16 1.383(4) . C11 C12 1.403(4) . C11 C17 1.500(4) . C12 C13 1.380(5) . C13 C14 1.376(6) . C14 C15 1.367(5) . C15 C16 1.387(4) . C17 C18 1.533(4) . C18 C19 1.500(4) . C21 O13 1.255(9) . C21 C22 1.599(17) 2_766 C22 O13 1.503(12) . C22 C21 1.599(17) 2_766