#------------------------------------------------------------------------------ #$Date: 2019-12-25 21:50:02 +0200 (Wed, 25 Dec 2019) $ #$Revision: 245798 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/31/13/2311328.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2311328 loop_ _publ_author_name 'Mohamed, Shaaban K.' 'Akkurt, Mehmet' 'Jasinski, Jerry P.' 'Abdelhamid, Antar A.' 'Tamam, Asmaa H.' 'Albayati, Mustafa R.' _publ_section_title ; Crystal structure of ethyl 2-[9-(5-bromo-2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetate. ; _journal_coeditor_code WM5239 _journal_issue 'Pt 12' _journal_name_full 'Acta crystallographica. Section E, Crystallographic communications' _journal_page_first o989 _journal_page_last 90 _journal_paper_doi 10.1107/S2056989015022240 _journal_volume 71 _journal_year 2015 _chemical_formula_iupac 'C23 H24 Br N O5' _chemical_formula_moiety 'C23 H24 Br N O5' _chemical_formula_sum 'C23 H24 Br N O5' _chemical_formula_weight 474.33 _chemical_name_systematic ;Ethyl 2-[9-(5-bromo-2-hydroxyphenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridin-10-yl]acetate ; _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens mixed _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 8.8287(3) _cell_length_b 14.2531(5) _cell_length_c 33.1222(11) _cell_measurement_reflns_used 4787 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.0970 _cell_measurement_theta_min 3.6620 _cell_volume 4168.0(2) _computing_cell_refinement ; CrysAlis PRO (Agilent, 2014) ; _computing_data_collection ; CrysAlis PRO (Agilent, 2014) ; _computing_data_reduction ; CrysAlis PRO (Agilent, 2014) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) ; _computing_publication_material ; PLATON (Spek, 2009) and PARST (Nardelli, 1995) ; _computing_structure_refinement ; SHELXL2014 (Sheldrick, 2015) ; _computing_structure_solution ; SHELXS2014 (Sheldrick, 2008) ; _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0416 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Agilent Xcalibur Eos Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0600 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_number 51745 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.24 _diffrn_reflns_theta_max 28.50 _diffrn_reflns_theta_min 2.92 _exptl_absorpt_coefficient_mu 2.008 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57924 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Agilent, 2014) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description needle _exptl_crystal_F_000 1952 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.532 _refine_diff_density_min -0.594 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 5281 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.0960 _refine_ls_R_factor_gt 0.0589 _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^)+(0.0520P)^2^+5.0593P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1333 _refine_ls_wR_factor_ref 0.1529 _reflns_number_gt 3379 _reflns_number_total 5281 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL wm5239 in Pbca CELL 0.71073 8.8287 14.2531 33.1222 90.000 90.000 90.000 ZERR 8.00 0.0003 0.0005 0.0011 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O BR UNIT 184 192 8 40 8 MERG 2 OMIT -4.00 57.00 DFIX 0.82 0.02 O5 H5 EADP C17A C17B EADP C16A C16B EQIV $1 -x+3/2, y+1/2, z HTAB C10 O4_$1 HTAB C14 O4_$1 HTAB O5 O1 HTAB C10 O4_$1 HTAB C14 O4_$1 HTAB O5 O1 FMAP 2 PLAN 3 SIZE 0.080 0.110 0.320 ACTA BOND BOND $H CONF L.S. 13 WGHT 0.052000 5.059300 FVAR 1.91800 0.76816 C1 1 0.347192 -0.190816 0.345643 11.00000 0.04904 0.04784 = 0.04941 0.00183 -0.00331 -0.01322 C2 1 0.192634 -0.160476 0.332520 11.00000 0.04604 0.07181 = 0.07443 0.00854 -0.01442 -0.01962 AFIX 23 H2A 2 0.196277 -0.141402 0.304425 11.00000 -1.20000 H2B 2 0.123456 -0.213113 0.334659 11.00000 -1.20000 AFIX 0 C3 1 0.135784 -0.082895 0.356865 11.00000 0.04022 0.10968 = 0.08385 -0.01026 -0.01066 0.00118 AFIX 23 H3A 2 0.118267 -0.104872 0.384186 11.00000 -1.20000 H3B 2 0.039426 -0.062250 0.345955 11.00000 -1.20000 AFIX 0 C4 1 0.243195 -0.000713 0.358094 11.00000 0.03662 0.06479 = 0.06230 0.00184 -0.00469 0.00903 AFIX 23 H4A 2 0.209683 0.043389 0.378531 11.00000 -1.20000 H4B 2 0.241513 0.031165 0.332224 11.00000 -1.20000 AFIX 0 C5 1 0.403006 -0.031391 0.367398 11.00000 0.03468 0.04350 = 0.03638 0.00443 0.00115 0.00269 C6 1 0.450476 -0.120573 0.361249 11.00000 0.03404 0.03954 = 0.03457 0.00210 0.00035 -0.00678 C7 1 0.610898 -0.150662 0.369810 11.00000 0.04209 0.02531 = 0.03656 -0.00113 -0.00235 0.00004 AFIX 13 H7 2 0.606010 -0.211022 0.383919 11.00000 -1.20000 AFIX 0 C8 1 0.684268 -0.081240 0.398117 11.00000 0.03491 0.02863 = 0.03206 -0.00262 0.00278 0.00091 C9 1 0.633654 0.007395 0.402117 11.00000 0.03589 0.03262 = 0.03643 0.00019 0.00216 0.00091 C10 1 0.715741 0.078224 0.427595 11.00000 0.05588 0.03572 = 0.06582 -0.01510 -0.00715 0.00237 AFIX 23 H10A 2 0.716187 0.138184 0.413743 11.00000 -1.20000 H10B 2 0.661968 0.086231 0.452900 11.00000 -1.20000 AFIX 0 C11 1 0.875663 0.049383 0.436242 11.00000 0.05812 0.05249 = 0.08312 -0.01886 -0.01646 -0.00588 AFIX 23 H11A 2 0.935325 0.054584 0.411752 11.00000 -1.20000 H11B 2 0.918849 0.091455 0.456176 11.00000 -1.20000 AFIX 0 C12 1 0.883480 -0.048559 0.451501 11.00000 0.05954 0.05480 = 0.06215 -0.01207 -0.02512 0.00621 AFIX 23 H12A 2 0.835682 -0.051752 0.477834 11.00000 -1.20000 H12B 2 0.988771 -0.066569 0.454652 11.00000 -1.20000 AFIX 0 C13 1 0.806642 -0.116229 0.423459 11.00000 0.04064 0.03858 = 0.04371 -0.00176 -0.00266 0.00486 C14 1 0.443795 0.131169 0.389585 11.00000 0.05182 0.03296 = 0.05706 0.00091 -0.00065 0.01079 AFIX 23 H14A 2 0.376531 0.147308 0.367495 11.00000 -1.20000 H14B 2 0.528715 0.174323 0.388931 11.00000 -1.20000 AFIX 0 C15 1 0.359665 0.143083 0.429241 11.00000 0.05299 0.04680 = 0.06412 -0.00510 0.00037 0.01062 PART 1 C16A 1 0.217280 0.244491 0.470395 21.00000 0.09806 0.06026 = 0.06954 -0.00677 0.01995 0.01268 AFIX 23 H16B 2 0.152571 0.191224 0.476288 21.00000 -1.20000 H16C 2 0.286949 0.252852 0.492752 21.00000 -1.20000 AFIX 0 C17A 1 0.125626 0.328988 0.464976 21.00000 0.13287 0.13420 = 0.06119 -0.00521 0.01142 0.08453 AFIX 33 H17A 2 0.067937 0.340565 0.489034 21.00000 -1.50000 H17B 2 0.058002 0.320344 0.442586 21.00000 -1.50000 H17C 2 0.190755 0.381538 0.459750 21.00000 -1.50000 AFIX 0 PART 2 C16B 1 0.261302 0.280792 0.468453 -21.00000 0.09806 0.06026 = 0.06954 -0.00677 0.01995 0.01268 AFIX 23 H16D 2 0.304085 0.253291 0.492692 -21.00000 -1.20000 H16E 2 0.292022 0.345976 0.466504 -21.00000 -1.20000 AFIX 0 C17B 1 0.107607 0.271458 0.467365 -21.00000 0.13287 0.13420 = 0.06119 -0.00521 0.01142 0.08453 AFIX 33 H17D 2 0.063734 0.304353 0.489791 -21.00000 -1.50000 H17E 2 0.081346 0.206202 0.468953 -21.00000 -1.50000 H17F 2 0.069560 0.297248 0.442585 -21.00000 -1.50000 AFIX 0 PART 0 C18 1 0.704048 -0.165476 0.331579 11.00000 0.03712 0.04230 = 0.03723 -0.01098 -0.00724 0.00684 C19 1 0.764721 -0.089181 0.311186 11.00000 0.03288 0.05145 = 0.03788 -0.00678 -0.00166 0.00517 AFIX 43 H19 2 0.743859 -0.028659 0.320083 11.00000 -1.20000 AFIX 0 C20 1 0.855509 -0.102389 0.277902 11.00000 0.03928 0.08276 = 0.04103 -0.00700 -0.00192 0.00509 C21 1 0.889397 -0.191859 0.264177 11.00000 0.04999 0.11062 = 0.04700 -0.02784 -0.00085 0.01996 AFIX 43 H21 2 0.953273 -0.200393 0.242155 11.00000 -1.20000 AFIX 0 C22 1 0.827761 -0.266826 0.283428 11.00000 0.07296 0.07008 = 0.06442 -0.03338 -0.00916 0.02470 AFIX 43 H22 2 0.848756 -0.326926 0.274037 11.00000 -1.20000 AFIX 0 C23 1 0.733981 -0.255909 0.316855 11.00000 0.05737 0.04883 = 0.05642 -0.01918 -0.00857 0.01197 N1 3 0.499707 0.035704 0.383661 11.00000 0.03875 0.03040 = 0.04664 -0.00116 -0.00206 0.00596 O1 4 0.386760 -0.273518 0.342494 11.00000 0.06631 0.04637 = 0.07898 -0.00608 -0.00769 -0.01894 O2 4 0.344792 0.083064 0.453912 11.00000 0.12786 0.07384 = 0.07391 0.01742 0.03613 0.03402 O3 4 0.303287 0.227607 0.432223 11.00000 0.08294 0.05653 = 0.07541 -0.01021 0.01143 0.02551 O4 4 0.842810 -0.198501 0.423076 11.00000 0.06845 0.03873 = 0.08059 -0.00527 -0.02631 0.01621 O5 4 0.676221 -0.334003 0.334759 11.00000 0.09856 0.03750 = 0.08522 -0.01813 -0.00743 0.00669 BR1 5 0.939213 0.003636 0.251379 11.00000 0.07601 0.11992 = 0.06076 0.00166 0.02581 -0.01832 H5 2 0.583911 -0.327386 0.338848 11.00000 -1.50000 HKLF 4 REM wm5239 in Pbca REM R1 = 0.0589 for 3379 Fo > 4sig(Fo) and 0.0960 for all 5281 data REM 281 parameters refined using 1 restraints END WGHT 0.0520 5.0594 REM Highest difference peak 0.532, deepest hole -0.594, 1-sigma level 0.054 Q1 1 0.9878 0.0222 0.2709 11.00000 0.05 0.53 Q2 1 0.1701 -0.0618 0.3280 11.00000 0.05 0.49 Q3 1 0.9530 -0.0594 0.2469 11.00000 0.05 0.47 ; _cod_data_source_file wm5239sup1.cif _cod_data_source_block I _cod_database_code 2311328 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,y,1/2-z 7 1/2-x,1/2+y,z 8 x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0760(3) 0.1199(4) 0.0608(3) -0.0183(3) 0.0258(2) 0.0017(2) O1 0.0663(16) 0.0464(14) 0.0790(18) -0.0189(12) -0.0077(13) -0.0061(12) O2 0.128(3) 0.0738(19) 0.0739(19) 0.0340(19) 0.0361(19) 0.0174(16) O3 0.0829(19) 0.0565(15) 0.0754(18) 0.0255(14) 0.0114(14) -0.0102(13) O4 0.0684(16) 0.0387(12) 0.0806(17) 0.0162(11) -0.0263(13) -0.0053(11) O5 0.099(2) 0.0375(13) 0.085(2) 0.0067(15) -0.0074(18) -0.0181(13) N1 0.0388(12) 0.0304(11) 0.0466(14) 0.0060(10) -0.0021(11) -0.0012(10) C1 0.0490(18) 0.0478(19) 0.0494(18) -0.0132(15) -0.0033(15) 0.0018(14) C2 0.0460(19) 0.072(2) 0.074(2) -0.0196(18) -0.0144(18) 0.009(2) C3 0.0402(19) 0.110(3) 0.084(3) 0.001(2) -0.011(2) -0.010(3) C4 0.0366(15) 0.065(2) 0.062(2) 0.0090(15) -0.0047(16) 0.0018(17) C5 0.0347(14) 0.0435(15) 0.0364(14) 0.0027(12) 0.0012(12) 0.0044(12) C6 0.0340(14) 0.0395(15) 0.0346(14) -0.0068(12) 0.0003(11) 0.0021(12) C7 0.0421(15) 0.0253(12) 0.0366(14) 0.0000(11) -0.0024(12) -0.0011(11) C8 0.0349(13) 0.0286(13) 0.0321(13) 0.0009(11) 0.0028(11) -0.0026(10) C9 0.0359(13) 0.0326(14) 0.0364(13) 0.0009(11) 0.0022(11) 0.0002(11) C10 0.056(2) 0.0357(16) 0.066(2) 0.0024(14) -0.0072(17) -0.0151(15) C11 0.058(2) 0.052(2) 0.083(3) -0.0059(17) -0.016(2) -0.0189(19) C12 0.060(2) 0.055(2) 0.062(2) 0.0062(17) -0.0251(18) -0.0121(17) C13 0.0406(15) 0.0386(16) 0.0437(16) 0.0049(13) -0.0027(13) -0.0018(13) C14 0.0518(18) 0.0330(15) 0.0571(19) 0.0108(14) -0.0006(15) 0.0009(14) C15 0.0530(19) 0.0468(19) 0.064(2) 0.0106(16) 0.0004(17) -0.0051(17) C16A 0.098(6) 0.060(5) 0.070(3) 0.013(4) 0.020(3) -0.007(4) C16B 0.098(6) 0.060(5) 0.070(3) 0.013(4) 0.020(3) -0.007(4) C17A 0.133(6) 0.134(9) 0.061(3) 0.085(7) 0.011(3) -0.005(5) C17B 0.133(6) 0.134(9) 0.061(3) 0.085(7) 0.011(3) -0.005(5) C18 0.0371(15) 0.0423(15) 0.0372(14) 0.0068(12) -0.0072(12) -0.0110(12) C19 0.0329(14) 0.0515(17) 0.0379(15) 0.0052(13) -0.0017(12) -0.0068(13) C20 0.0393(16) 0.083(2) 0.0410(17) 0.0051(17) -0.0019(14) -0.0070(17) C21 0.050(2) 0.111(3) 0.0470(19) 0.020(2) -0.0008(17) -0.028(2) C22 0.073(3) 0.070(3) 0.064(2) 0.025(2) -0.009(2) -0.033(2) C23 0.057(2) 0.0488(19) 0.056(2) 0.0120(17) -0.0086(17) -0.0192(16) loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy Br Br1 0.93921(6) 0.00364(4) 0.25138(2) 0.0856(2) Uani d . 1.000 O O1 0.3868(3) -0.27352(16) 0.34249(8) 0.0639(9) Uani d . 1.000 O O2 0.3448(4) 0.0831(2) 0.45391(9) 0.0919(13) Uani d . 1.000 O O3 0.3033(3) 0.22761(18) 0.43222(9) 0.0716(10) Uani d . 1.000 O O4 0.8428(3) -0.19850(15) 0.42308(8) 0.0626(9) Uani d . 1.000 O O5 0.6762(3) -0.33400(18) 0.33476(10) 0.0738(10) Uani d D 1.000 N N1 0.4997(3) 0.03570(15) 0.38366(7) 0.0386(7) Uani d . 1.000 C C1 0.3472(4) -0.1908(2) 0.34564(10) 0.0487(11) Uani d . 1.000 C C2 0.1926(4) -0.1605(3) 0.33252(13) 0.0640(11) Uani d . 1.000 C C3 0.1358(4) -0.0829(3) 0.35687(14) 0.0781(15) Uani d . 1.000 C C4 0.2432(4) -0.0007(2) 0.35809(11) 0.0545(11) Uani d . 1.000 C C5 0.4030(3) -0.0314(2) 0.36740(9) 0.0382(8) Uani d . 1.000 C C6 0.4505(3) -0.12057(19) 0.36125(8) 0.0360(8) Uani d . 1.000 C C7 0.6109(3) -0.15066(18) 0.36981(8) 0.0347(8) Uani d . 1.000 C C8 0.6843(3) -0.08124(18) 0.39812(8) 0.0319(8) Uani d . 1.000 C C9 0.6337(3) 0.00739(18) 0.40212(8) 0.0350(8) Uani d . 1.000 C C10 0.7157(4) 0.0782(2) 0.42760(11) 0.0526(11) Uani d . 1.000 C C11 0.8757(4) 0.0494(2) 0.43624(13) 0.0643(14) Uani d . 1.000 C C12 0.8835(4) -0.0486(2) 0.45150(11) 0.0590(12) Uani d . 1.000 C C13 0.8066(3) -0.1162(2) 0.42346(9) 0.0410(9) Uani d . 1.000 C C14 0.4438(4) 0.1312(2) 0.38959(10) 0.0473(10) Uani d . 1.000 C C15 0.3597(4) 0.1431(2) 0.42924(12) 0.0546(11) Uani d . 1.000 C C16A 0.2173(11) 0.2445(7) 0.4704(2) 0.076(3) Uani . . 0.768(17) C C16B 0.261(4) 0.281(2) 0.4685(9) 0.076(3) Uani . . 0.232(17) C C17A 0.1256(11) 0.3290(10) 0.4650(2) 0.109(4) Uani . . 0.768(17) C C17B 0.108(5) 0.271(3) 0.4674(9) 0.109(4) Uani . . 0.232(17) C C18 0.7040(3) -0.1655(2) 0.33158(9) 0.0389(8) Uani d . 1.000 C C19 0.7647(3) -0.0892(2) 0.31119(8) 0.0408(9) Uani d . 1.000 C C20 0.8555(4) -0.1024(3) 0.27790(10) 0.0544(10) Uani d . 1.000 C C21 0.8894(4) -0.1919(4) 0.26418(11) 0.0693(14) Uani d . 1.000 C C22 0.8278(5) -0.2668(3) 0.28343(12) 0.0690(16) Uani d . 1.000 C C23 0.7340(4) -0.2559(2) 0.31685(11) 0.0539(11) Uani d . 1.000 H H2A 0.19630 -0.14140 0.30440 0.0770 Uiso c RU 1.000 H H2B 0.12350 -0.21310 0.33470 0.0770 Uiso c RU 1.000 H H3A 0.11830 -0.10490 0.38420 0.0940 Uiso c RU 1.000 H H3B 0.03940 -0.06220 0.34600 0.0940 Uiso c RU 1.000 H H4A 0.20970 0.04340 0.37850 0.0650 Uiso c RU 1.000 H H4B 0.24150 0.03120 0.33220 0.0650 Uiso c RU 1.000 H H5 0.584(3) -0.327(4) 0.3388(18) 0.1280 Uiso d DU 1.000 H H7 0.60600 -0.21100 0.38390 0.0420 Uiso c RU 1.000 H H10A 0.71620 0.13820 0.41370 0.0630 Uiso c RU 1.000 H H10B 0.66200 0.08620 0.45290 0.0630 Uiso c RU 1.000 H H11A 0.93530 0.05460 0.41180 0.0770 Uiso c RU 1.000 H H11B 0.91880 0.09150 0.45620 0.0770 Uiso c RU 1.000 H H12A 0.83570 -0.05180 0.47780 0.0710 Uiso c RU 1.000 H H12B 0.98880 -0.06660 0.45470 0.0710 Uiso c RU 1.000 H H14A 0.37650 0.14730 0.36750 0.0570 Uiso c RU 1.000 H H14B 0.52870 0.17430 0.38890 0.0570 Uiso c RU 1.000 H H16B 0.15260 0.19120 0.47630 0.0910 Uiso . . 0.768(17) H H16C 0.28690 0.25290 0.49280 0.0910 Uiso . . 0.768(17) H H16D 0.30410 0.25330 0.49270 0.0910 Uiso . . 0.232(17) H H16E 0.29200 0.34600 0.46650 0.0910 Uiso . . 0.232(17) H H17A 0.06790 0.34060 0.48900 0.1640 Uiso . . 0.768(17) H H17B 0.05800 0.32030 0.44260 0.1640 Uiso . . 0.768(17) H H17C 0.19080 0.38150 0.45980 0.1640 Uiso . . 0.768(17) H H17D 0.06370 0.30440 0.48980 0.1640 Uiso . . 0.232(17) H H17E 0.08130 0.20620 0.46900 0.1640 Uiso . . 0.232(17) H H17F 0.06960 0.29720 0.44260 0.1640 Uiso . . 0.232(17) H H19 0.74390 -0.02870 0.32010 0.0490 Uiso c RU 1.000 H H21 0.95330 -0.20040 0.24220 0.0830 Uiso c RU 1.000 H H22 0.84880 -0.32690 0.27400 0.0830 Uiso c RU 1.000 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' 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_publ_flag C15 O3 C16A 113.9(5) no C15 O3 C16B 129.4(12) no C5 N1 C9 119.5(2) no C5 N1 C14 119.0(3) no C9 N1 C14 119.9(2) no C23 O5 H5 110(4) no O1 C1 C6 120.8(3) no C2 C1 C6 118.6(3) no O1 C1 C2 120.6(3) no C1 C2 C3 111.9(3) no C2 C3 C4 112.8(3) no C3 C4 C5 111.6(3) no C4 C5 C6 122.1(3) no N1 C5 C6 120.9(2) no N1 C5 C4 117.0(2) no C1 C6 C5 120.5(3) no C5 C6 C7 122.0(2) no C1 C6 C7 117.5(2) no C6 C7 C8 109.5(2) no C6 C7 C18 113.0(2) no C8 C7 C18 112.1(2) no C9 C8 C13 120.7(2) no C7 C8 C13 116.9(2) no C7 C8 C9 122.3(2) no C8 C9 C10 121.7(3) no N1 C9 C8 120.7(2) no N1 C9 C10 117.5(2) no C9 C10 C11 112.2(3) no C10 C11 C12 111.5(3) no C11 C12 C13 111.8(3) no O4 C13 C12 120.5(3) no O4 C13 C8 121.3(3) no C8 C13 C12 118.2(2) no N1 C14 C15 112.7(2) no O3 C15 C14 110.8(3) no O2 C15 O3 124.6(4) no O2 C15 C14 124.6(3) no O3 C16A C17A 108.1(6) no O3 C16B C17B 100(2) no C7 C18 C23 121.2(3) no C7 C18 C19 120.3(2) no C19 C18 C23 118.5(3) no C18 C19 C20 120.5(3) no Br1 C20 C19 119.3(3) no C19 C20 C21 120.9(4) no Br1 C20 C21 119.8(3) no C20 C21 C22 118.9(3) no C21 C22 C23 121.6(4) no C18 C23 C22 119.5(3) no O5 C23 C18 121.9(3) no O5 C23 C22 118.6(3) no C3 C2 H2A 109.00 no C3 C2 H2B 109.00 no H2A C2 H2B 108.00 no C1 C2 H2B 109.00 no C1 C2 H2A 109.00 no C4 C3 H3B 109.00 no C4 C3 H3A 109.00 no H3A C3 H3B 108.00 no C2 C3 H3A 109.00 no C2 C3 H3B 109.00 no C3 C4 H4A 109.00 no C5 C4 H4B 109.00 no C3 C4 H4B 109.00 no H4A C4 H4B 108.00 no C5 C4 H4A 109.00 no C6 C7 H7 107.00 no C8 C7 H7 107.00 no C18 C7 H7 107.00 no C9 C10 H10A 109.00 no C9 C10 H10B 109.00 no C11 C10 H10A 109.00 no H10A C10 H10B 108.00 no C11 C10 H10B 109.00 no C10 C11 H11B 109.00 no C10 C11 H11A 109.00 no H11A C11 H11B 108.00 no C12 C11 H11A 109.00 no C12 C11 H11B 109.00 no C13 C12 H12A 109.00 no C13 C12 H12B 109.00 no H12A C12 H12B 108.00 no C11 C12 H12A 109.00 no C11 C12 H12B 109.00 no N1 C14 H14A 109.00 no C15 C14 H14A 109.00 no N1 C14 H14B 109.00 no H14A C14 H14B 108.00 no C15 C14 H14B 109.00 no H16B C16A H16C 108.00 no O3 C16A H16B 110.00 no C17A C16A H16C 110.00 no C17A C16A H16B 110.00 no O3 C16A H16C 110.00 no C17B C16B H16D 112.00 no C17B C16B H16E 112.00 no O3 C16B H16E 112.00 no O3 C16B H16D 111.00 no H16D C16B H16E 110.00 no H17A C17A H17C 109.00 no H17B C17A H17C 110.00 no C16A C17A H17B 109.00 no C16A C17A H17C 109.00 no C16A C17A H17A 110.00 no H17A C17A H17B 109.00 no C16B C17B H17D 109.00 no C16B C17B H17E 110.00 no H17D C17B H17F 109.00 no H17E C17B H17F 110.00 no C16B C17B H17F 109.00 no H17D C17B H17E 110.00 no C20 C19 H19 120.00 no C18 C19 H19 120.00 no C22 C21 H21 121.00 no C20 C21 H21 121.00 no C21 C22 H22 119.00 no C23 C22 H22 119.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C20 1.898(4) no O1 C1 1.234(4) no O2 C15 1.190(5) no O3 C16A 1.495(8) no O3 C15 1.307(4) no O3 C16B 1.47(3) no O4 C13 1.216(4) no O5 C23 1.361(4) no N1 C5 1.391(4) no N1 C9 1.392(4) no N1 C14 1.461(4) no O5 H5 0.83(3) no C1 C2 1.496(5) no C1 C6 1.450(4) no C2 C3 1.458(6) no C3 C4 1.508(5) no C4 C5 1.509(4) no C5 C6 1.354(4) no C6 C7 1.507(4) no C7 C8 1.509(4) no C7 C18 1.524(4) no C8 C13 1.456(4) no C8 C9 1.347(4) no C9 C10 1.502(4) no C10 C11 1.499(5) no C11 C12 1.487(4) no C12 C13 1.501(4) no C14 C15 1.518(5) no C16A C17A 1.462(16) no C16B C17B 1.36(6) no C18 C23 1.403(4) no C18 C19 1.388(4) no C19 C20 1.376(4) no C20 C21 1.387(7) no C21 C22 1.357(7) no C22 C23 1.391(5) no C2 H2B 0.9700 no C2 H2A 0.9700 no C3 H3B 0.9700 no C3 H3A 0.9700 no C4 H4B 0.9700 no C4 H4A 0.9700 no C7 H7 0.9800 no C10 H10A 0.9700 no C10 H10B 0.9700 no C11 H11A 0.9700 no C11 H11B 0.9700 no C12 H12A 0.9700 no C12 H12B 0.9700 no C14 H14A 0.9700 no C14 H14B 0.9700 no C16A H16C 0.9700 no C16A H16B 0.9700 no C16B H16E 0.9700 no C16B H16D 0.9700 no C17A H17C 0.9600 no C17A H17A 0.9600 no C17A H17B 0.9600 no C17B H17D 0.9600 no C17B H17F 0.9600 no C17B H17E 0.9500 no C19 H19 0.9300 no C21 H21 0.9300 no C22 H22 0.9300 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O5 H5 O1 . 0.83(3) 1.91(3) 2.709(4) 163(6) yes C7 H7 O5 . 0.98 2.47 2.917(4) 107 no C10 H10A O4 7_655 0.97 2.41 3.228(4) 142 yes C14 H14B O4 7_655 0.97 2.42 3.267(4) 146 yes 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_publ_flag C16A O3 C15 O2 0.7(6) no C16A O3 C15 C14 179.5(4) no C15 O3 C16A C17A -163.9(6) no C14 N1 C9 C8 177.7(3) no C9 N1 C14 C15 -81.1(3) no C14 N1 C5 C4 -1.8(4) no C5 N1 C14 C15 84.6(3) no C14 N1 C5 C6 179.7(3) no C9 N1 C5 C4 164.0(3) no C5 N1 C9 C8 12.1(4) no C5 N1 C9 C10 -165.8(3) no C14 N1 C9 C10 -0.2(4) no C9 N1 C5 C6 -14.5(4) no C2 C1 C6 C7 -173.2(3) no C6 C1 C2 C3 -33.1(5) no O1 C1 C6 C7 5.4(4) no O1 C1 C6 C5 -175.2(3) no O1 C1 C2 C3 148.3(4) no C2 C1 C6 C5 6.2(5) no C1 C2 C3 C4 54.1(5) no C2 C3 C4 C5 -48.2(5) no C3 C4 C5 N1 -157.2(3) no C3 C4 C5 C6 21.3(4) no C4 C5 C6 C1 -0.6(4) no C4 C5 C6 C7 178.8(3) no N1 C5 C6 C1 177.8(3) no N1 C5 C6 C7 -2.8(4) no C5 C6 C7 C8 19.6(4) no C1 C6 C7 C8 -160.9(2) no C5 C6 C7 C18 -106.0(3) no C1 C6 C7 C18 73.4(3) no C8 C7 C18 C19 -45.0(3) no C8 C7 C18 C23 133.2(3) no C6 C7 C8 C13 153.5(2) no C18 C7 C8 C9 104.1(3) no C6 C7 C18 C23 -102.6(3) no C6 C7 C18 C19 79.3(3) no C6 C7 C8 C9 -22.1(3) no C18 C7 C8 C13 -80.4(3) no C7 C8 C13 C12 179.1(3) no C9 C8 C13 O4 172.3(3) no C7 C8 C9 N1 7.6(4) no C7 C8 C9 C10 -174.6(3) no C7 C8 C13 O4 -3.3(4) no C13 C8 C9 N1 -167.8(2) no C9 C8 C13 C12 -5.2(4) no C13 C8 C9 C10 10.0(4) no C8 C9 C10 C11 17.9(4) no N1 C9 C10 C11 -164.2(3) no C9 C10 C11 C12 -49.8(4) no C10 C11 C12 C13 54.3(4) no C11 C12 C13 C8 -27.2(4) no C11 C12 C13 O4 155.2(3) no N1 C14 C15 O3 -175.9(3) no N1 C14 C15 O2 2.8(5) no C7 C18 C19 C20 176.5(3) no C23 C18 C19 C20 -1.7(4) no C7 C18 C23 O5 3.0(5) no C7 C18 C23 C22 -175.7(3) no C19 C18 C23 O5 -178.8(3) no C19 C18 C23 C22 2.5(5) no C18 C19 C20 Br1 -178.9(2) no C18 C19 C20 C21 -0.5(5) no Br1 C20 C21 C22 -179.7(3) no C19 C20 C21 C22 1.9(5) no C20 C21 C22 C23 -1.1(6) no C21 C22 C23 O5 -179.9(4) no C21 C22 C23 C18 -1.1(6) no