#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:31:20 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270481 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060999.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_7060999 loop_ _publ_author_name 'Xu, Feng-Shun' 'Yan, Chen' 'Sun, Jing' 'Yan, Chao-Guo' _publ_section_title ; Efficient synthesis of tetra- and penta-substituted benzenes via a domino annulation reaction of a pyridinium ylide and chalcone o-enolate ; _journal_issue 42 _journal_name_full 'New Journal of Chemistry' _journal_page_first 19666 _journal_page_last 19670 _journal_paper_doi 10.1039/D1NJ03772B _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C28 H21 Cl O5' _chemical_formula_sum 'C28 H21 Cl O5' _chemical_formula_weight 472.90 _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 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-07-26 deposited with the CCDC. 2021-09-17 downloaded from the CCDC. ; _cell_angle_alpha 83.296(3) _cell_angle_beta 76.282(3) _cell_angle_gamma 66.624(3) _cell_formula_units_Z 2 _cell_length_a 9.6420(9) _cell_length_b 9.6811(10) _cell_length_c 14.0972(13) _cell_measurement_reflns_used 6691 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.86 _cell_measurement_theta_min 2.29 _cell_volume 1173.1(2) _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 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _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 0.0307 _diffrn_reflns_av_unetI/netI 0.0336 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 16665 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.000 _diffrn_reflns_theta_min 2.293 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6578 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.339 _exptl_crystal_description block _exptl_crystal_F_000 492 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.180 _refine_diff_density_max 0.178 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.030 _refine_ls_extinction_coef 0.055(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 1.014 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 315 _refine_ls_number_reflns 4586 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0420 _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^)+(0.0386P)^2^+0.3089P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.1034 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3181 _reflns_number_total 4586 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03772b2.cif _cod_data_source_block 3h _cod_depositor_comments 'Adding full bibliography for 7060998--7060999.cif.' _cod_database_code 7060999 _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 0.939 _shelx_estimated_absorpt_t_max 0.965 _shelx_res_file ; XFS20210120.res created by SHELXL-2014/7 TITL XFS20210120 in P-1 CELL 0.71073 9.64200 9.68110 14.09720 83.2956 76.2819 66.6236 ZERR 2.00 0.00090 0.00100 0.00130 0.0030 0.0029 0.0029 LATT 1 SFAC C H O Cl UNIT 56 42 10 2 OMIT -3 52 OMIT 0 0 1 OMIT 1 0 0 OMIT 1 1 0 L.S. 20 ACTA SIZE 0.32 0.22 0.18 BOND $H HTAB O1 O2 EADP Cl1 Cl1' FMAP 2 PLAN 20 FREE Cl1 Cl1' TEMP 23 WGHT 0.038600 0.308900 EXTI 0.055402 FVAR 0.38404 0.91210 MOLE 1 C1 1 0.907140 -0.038887 0.676914 11.00000 0.06072 0.06995 = 0.06753 -0.01634 -0.00223 -0.03295 C2 1 0.855771 -0.040008 0.592996 11.00000 0.08377 0.09437 = 0.07837 -0.03357 -0.00662 -0.04086 AFIX 43 H2 2 0.883842 -0.130617 0.563043 11.00000 -1.20000 AFIX 0 C3 1 0.764931 0.090179 0.554440 11.00000 0.08663 0.12088 = 0.07039 -0.02186 -0.02135 -0.04928 AFIX 43 H3 2 0.731318 0.087730 0.498266 11.00000 -1.20000 AFIX 0 C4 1 0.721343 0.227286 0.597728 11.00000 0.07624 0.09839 = 0.07945 -0.00249 -0.03290 -0.03335 AFIX 43 H4 2 0.657838 0.315856 0.571387 11.00000 -1.20000 AFIX 0 C5 1 0.773319 0.230132 0.679864 11.00000 0.05892 0.06930 = 0.07065 -0.00777 -0.01768 -0.02652 AFIX 43 H5 2 0.744749 0.321674 0.708787 11.00000 -1.20000 AFIX 0 C6 1 0.868245 0.098297 0.720858 11.00000 0.04717 0.05881 = 0.05276 -0.00970 -0.00169 -0.02809 C7 1 0.923500 0.099239 0.809175 11.00000 0.04361 0.05076 = 0.05275 -0.00145 -0.00134 -0.02390 C8 1 0.885944 0.244916 0.855832 11.00000 0.04050 0.04468 = 0.04702 -0.00134 -0.00871 -0.01863 C9 1 0.938203 0.358000 0.810862 11.00000 0.04079 0.04655 = 0.04292 0.00115 -0.00996 -0.01864 C10 1 1.051339 0.337972 0.715953 11.00000 0.04579 0.05222 = 0.04075 -0.00126 -0.00766 -0.02474 C11 1 1.036022 0.455646 0.647162 11.00000 0.05925 0.06241 = 0.04835 0.00479 -0.01025 -0.02539 AFIX 43 H11 2 0.950341 0.545467 0.658985 11.00000 -1.20000 AFIX 0 C12 1 1.145780 0.441614 0.561522 11.00000 0.07660 0.08501 = 0.04435 0.01367 -0.01481 -0.04276 AFIX 43 H12 2 1.134574 0.521406 0.516385 11.00000 -1.20000 AFIX 0 C13 1 1.271248 0.308605 0.544053 11.00000 0.06219 0.09736 = 0.03826 -0.00847 -0.00077 -0.04074 C14 1 1.290479 0.189868 0.610281 11.00000 0.05665 0.07505 = 0.05162 -0.01002 -0.00124 -0.02459 AFIX 43 H14 2 1.376202 0.100254 0.597598 11.00000 -1.20000 AFIX 0 C15 1 1.180816 0.205361 0.695940 11.00000 0.05508 0.05713 = 0.04540 -0.00100 -0.00707 -0.02446 AFIX 43 H15 2 1.193902 0.125477 0.741093 11.00000 -1.20000 AFIX 0 C16 1 0.795752 0.264826 0.950158 11.00000 0.03917 0.04700 = 0.05207 0.00286 -0.00614 -0.02244 AFIX 43 H16 2 0.764455 0.188440 0.980762 11.00000 -1.20000 AFIX 0 C17 1 0.751943 0.396183 0.999084 11.00000 0.03442 0.04732 = 0.04646 -0.00178 -0.00495 -0.01875 C18 1 0.664815 0.405323 1.102852 11.00000 0.04455 0.04743 = 0.05374 -0.00288 -0.00075 -0.02245 C19 1 0.669508 0.445518 1.263652 11.00000 0.07957 0.14751 = 0.04877 -0.01611 0.00292 -0.04364 AFIX 137 H19A 2 0.585934 0.542276 1.267919 11.00000 -1.50000 H19B 2 0.740702 0.444284 1.301493 11.00000 -1.50000 H19C 2 0.629460 0.369081 1.288529 11.00000 -1.50000 AFIX 0 C20 1 0.888371 0.490983 0.860201 11.00000 0.04394 0.04531 = 0.04616 0.00502 -0.00836 -0.02277 AFIX 43 H20 2 0.919797 0.567392 0.829805 11.00000 -1.20000 AFIX 0 C21 1 0.793655 0.514971 0.952951 11.00000 0.03489 0.04571 = 0.04712 0.00072 -0.00949 -0.01780 C22 1 0.738873 0.660672 1.001110 11.00000 0.03743 0.04399 = 0.04290 0.00050 -0.00846 -0.01643 C23 1 0.587144 0.726281 1.051915 11.00000 0.03933 0.05061 = 0.06262 -0.00403 -0.00702 -0.02315 AFIX 43 H23 2 0.519353 0.679047 1.053468 11.00000 -1.20000 AFIX 0 C24 1 0.534081 0.859418 1.100124 11.00000 0.03988 0.04987 = 0.05680 -0.00342 -0.00231 -0.01714 AFIX 43 H24 2 0.432063 0.900791 1.133951 11.00000 -1.20000 AFIX 0 C25 1 0.633719 0.930861 1.097764 11.00000 0.04974 0.04116 = 0.04430 0.00107 -0.01135 -0.01738 C26 1 0.441740 1.125058 1.200701 11.00000 0.07776 0.06036 = 0.05883 -0.01469 0.00831 -0.02609 AFIX 137 H26A 2 0.369189 1.145779 1.159474 11.00000 -1.50000 H26B 2 0.427687 1.217009 1.228244 11.00000 -1.50000 H26C 2 0.425063 1.055713 1.252287 11.00000 -1.50000 AFIX 0 C27 1 0.784488 0.870042 1.044578 11.00000 0.04575 0.04779 = 0.05249 0.00543 -0.01343 -0.02575 AFIX 43 H27 2 0.850949 0.919443 1.041165 11.00000 -1.20000 AFIX 0 C28 1 0.835862 0.737194 0.996982 11.00000 0.03543 0.04637 = 0.04720 0.00335 -0.00677 -0.01766 AFIX 43 H28 2 0.936980 0.697740 0.961450 11.00000 -1.20000 AFIX 0 PART 1 21 CL1 4 1.411392 0.289730 0.436487 21.00000 0.08605 0.15323 = 0.04735 -0.00187 0.01191 -0.04990 PART 2 -21 CL1' 4 1.361850 0.323259 0.419421 -21.00000 0.08605 0.15323 = 0.04735 -0.00187 0.01191 -0.04990 PART 0 O1 3 0.993689 -0.172072 0.712890 11.00000 0.11342 0.05893 = 0.10177 -0.02104 -0.02893 -0.02508 AFIX 147 H1 2 1.016671 -0.158526 0.762454 11.00000 -1.50000 AFIX 0 O2 3 0.995021 -0.019650 0.849518 11.00000 0.07832 0.04930 = 0.06630 0.00084 -0.01648 -0.02414 O3 3 0.538239 0.402803 1.129680 11.00000 0.05324 0.08877 = 0.06912 -0.00876 0.00778 -0.04474 O4 3 0.748401 0.416795 1.162856 11.00000 0.05026 0.08819 = 0.04454 -0.00372 -0.00259 -0.03007 O5 3 0.595278 1.060645 1.144355 11.00000 0.06340 0.05228 = 0.06904 -0.01322 -0.00452 -0.02404 HKLF 4 REM XFS20210120 in P-1 REM R1 = 0.0420 for 3181 Fo > 4sig(Fo) and 0.0720 for all 4586 data REM 315 parameters refined using 0 restraints END WGHT 0.0385 0.3086 REM Highest difference peak 0.178, deepest hole -0.157, 1-sigma level 0.030 Q1 1 0.5388 0.4613 1.2829 11.00000 0.05 0.18 Q2 1 0.9878 0.3433 0.7596 11.00000 0.05 0.16 Q3 1 1.2641 0.2276 0.5564 11.00000 0.05 0.15 Q4 1 1.3983 0.3644 0.4884 11.00000 0.05 0.14 Q5 1 0.7022 0.4181 1.0443 11.00000 0.05 0.14 Q6 1 0.7551 0.4635 0.9706 11.00000 0.05 0.14 Q7 1 0.8747 0.2392 0.9098 11.00000 0.05 0.14 Q8 1 0.7220 0.8719 1.1039 11.00000 0.05 0.14 Q9 1 0.6140 0.3314 1.1672 11.00000 0.05 0.13 Q10 1 1.0084 0.3824 0.6675 11.00000 0.05 0.12 Q11 1 1.3422 0.2843 0.5056 11.00000 0.05 0.12 Q12 1 0.7251 0.3586 0.9527 11.00000 0.05 0.12 Q13 1 1.1341 0.2995 0.7254 11.00000 0.05 0.12 Q14 1 0.7624 0.5359 0.8908 11.00000 0.05 0.12 Q15 1 0.7832 0.4422 0.9824 11.00000 0.05 0.12 Q16 1 1.2020 0.3468 0.5294 11.00000 0.05 0.12 Q17 1 0.8702 0.4769 0.9219 11.00000 0.05 0.12 Q18 1 1.0609 -0.0246 0.7873 11.00000 0.05 0.11 Q19 1 0.9380 0.2809 0.8362 11.00000 0.05 0.11 Q20 1 0.7527 0.3597 1.3117 11.00000 0.05 0.11 ; _shelx_res_checksum 93364 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9071(2) -0.0389(2) 0.67691(15) 0.0643(5) Uani 1 1 d . . . . . C2 C 0.8558(3) -0.0400(3) 0.59300(18) 0.0825(7) Uani 1 1 d . . . . . H2 H 0.8838 -0.1306 0.5630 0.099 Uiso 1 1 calc R U . . . C3 C 0.7649(3) 0.0902(3) 0.55444(18) 0.0870(7) Uani 1 1 d . . . . . H3 H 0.7313 0.0877 0.4983 0.104 Uiso 1 1 calc R U . . . C4 C 0.7213(3) 0.2273(3) 0.59773(17) 0.0817(7) Uani 1 1 d . . . . . H4 H 0.6578 0.3159 0.5714 0.098 Uiso 1 1 calc R U . . . C5 C 0.7733(2) 0.2301(2) 0.67986(15) 0.0644(5) Uani 1 1 d . . . . . H5 H 0.7447 0.3217 0.7088 0.077 Uiso 1 1 calc R U . . . C6 C 0.8682(2) 0.0983(2) 0.72086(13) 0.0513(5) Uani 1 1 d . . . . . C7 C 0.92350(19) 0.0992(2) 0.80918(13) 0.0487(4) Uani 1 1 d . . . . . C8 C 0.88594(18) 0.24492(18) 0.85583(12) 0.0434(4) Uani 1 1 d . . . . . C9 C 0.93820(18) 0.35800(18) 0.81086(12) 0.0428(4) Uani 1 1 d . . . . . C10 C 1.05134(19) 0.33797(19) 0.71595(12) 0.0446(4) Uani 1 1 d . . . . . C11 C 1.0360(2) 0.4556(2) 0.64716(13) 0.0567(5) Uani 1 1 d . . . . . H11 H 0.9503 0.5455 0.6590 0.068 Uiso 1 1 calc R U . . . C12 C 1.1458(3) 0.4416(3) 0.56152(14) 0.0658(6) Uani 1 1 d . . . . . H12 H 1.1346 0.5214 0.5164 0.079 Uiso 1 1 calc R U . . . C13 C 1.2712(2) 0.3086(3) 0.54405(13) 0.0638(6) Uani 1 1 d . . . . . C14 C 1.2905(2) 0.1899(2) 0.61028(14) 0.0624(5) Uani 1 1 d . . . . . H14 H 1.3762 0.1003 0.5976 0.075 Uiso 1 1 calc R U . . . C15 C 1.1808(2) 0.2054(2) 0.69594(13) 0.0522(5) Uani 1 1 d . . . . . H15 H 1.1939 0.1255 0.7411 0.063 Uiso 1 1 calc R U . . . C16 C 0.79575(18) 0.26483(19) 0.95016(12) 0.0451(4) Uani 1 1 d . . . . . H16 H 0.7645 0.1884 0.9808 0.054 Uiso 1 1 calc R U . . . C17 C 0.75194(17) 0.39618(18) 0.99908(12) 0.0423(4) Uani 1 1 d . . . . . C18 C 0.6648(2) 0.40532(19) 1.10285(13) 0.0486(4) Uani 1 1 d . . . . . C19 C 0.6695(3) 0.4455(3) 1.26365(15) 0.0937(8) Uani 1 1 d . . . . . H19A H 0.5859 0.5423 1.2679 0.140 Uiso 1 1 calc R U . . . H19B H 0.7407 0.4443 1.3015 0.140 Uiso 1 1 calc R U . . . H19C H 0.6295 0.3691 1.2885 0.140 Uiso 1 1 calc R U . . . C20 C 0.88837(18) 0.49098(19) 0.86020(12) 0.0440(4) Uani 1 1 d . . . . . H20 H 0.9198 0.5674 0.8298 0.053 Uiso 1 1 calc R U . . . C21 C 0.79365(17) 0.51497(18) 0.95295(12) 0.0418(4) Uani 1 1 d . . . . . C22 C 0.73887(17) 0.66067(18) 1.00111(11) 0.0413(4) Uani 1 1 d . . . . . C23 C 0.58714(19) 0.72628(19) 1.05192(13) 0.0494(4) Uani 1 1 d . . . . . H23 H 0.5194 0.6790 1.0535 0.059 Uiso 1 1 calc R U . . . C24 C 0.53408(19) 0.8594(2) 1.10012(13) 0.0501(4) Uani 1 1 d . . . . . H24 H 0.4321 0.9008 1.1340 0.060 Uiso 1 1 calc R U . . . C25 C 0.63372(19) 0.93086(18) 1.09776(12) 0.0450(4) Uani 1 1 d . . . . . C26 C 0.4417(2) 1.1251(2) 1.20070(15) 0.0687(6) Uani 1 1 d . . . . . H26A H 0.3692 1.1458 1.1595 0.103 Uiso 1 1 calc R U . . . H26B H 0.4277 1.2170 1.2282 0.103 Uiso 1 1 calc R U . . . H26C H 0.4251 1.0557 1.2523 0.103 Uiso 1 1 calc R U . . . C27 C 0.78449(19) 0.87004(19) 1.04458(12) 0.0462(4) Uani 1 1 d . . . . . H27 H 0.8509 0.9194 1.0412 0.055 Uiso 1 1 calc R U . . . C28 C 0.83586(18) 0.73719(18) 0.99698(12) 0.0431(4) Uani 1 1 d . . . . . H28 H 0.9370 0.6977 0.9615 0.052 Uiso 1 1 calc R U . . . Cl1 Cl 1.4114(5) 0.2897(4) 0.43649(19) 0.0990(7) Uani 0.912(15) 1 d . . P A 1 Cl1' Cl 1.362(4) 0.323(3) 0.4194(14) 0.0990(7) Uani 0.088(15) 1 d . . P A 2 O1 O 0.9937(2) -0.17207(17) 0.71289(13) 0.0911(5) Uani 1 1 d . . . . . H1 H 1.0167 -0.1585 0.7625 0.137 Uiso 1 1 calc R U . . . O2 O 0.99502(16) -0.01965(14) 0.84952(10) 0.0647(4) Uani 1 1 d . . . . . O3 O 0.53824(15) 0.40280(16) 1.12968(10) 0.0679(4) Uani 1 1 d . . . . . O4 O 0.74840(14) 0.41679(15) 1.16286(9) 0.0610(4) Uani 1 1 d . . . . . O5 O 0.59528(15) 1.06064(14) 1.14435(10) 0.0616(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 C1 0.0607(12) 0.0699(15) 0.0675(13) -0.0163(11) -0.0022(10) -0.0330(11) C2 0.0838(16) 0.0944(19) 0.0784(16) -0.0336(14) -0.0066(14) -0.0409(15) C3 0.0866(17) 0.121(2) 0.0704(15) -0.0219(16) -0.0214(13) -0.0493(17) C4 0.0762(15) 0.0984(19) 0.0794(15) -0.0025(14) -0.0329(13) -0.0334(14) C5 0.0589(12) 0.0693(14) 0.0706(13) -0.0078(11) -0.0177(11) -0.0265(11) C6 0.0472(10) 0.0588(12) 0.0528(10) -0.0097(9) -0.0017(8) -0.0281(9) C7 0.0436(9) 0.0508(11) 0.0527(10) -0.0014(9) -0.0013(8) -0.0239(9) C8 0.0405(9) 0.0447(10) 0.0470(9) -0.0013(8) -0.0087(7) -0.0186(8) C9 0.0408(9) 0.0466(10) 0.0429(9) 0.0012(8) -0.0100(7) -0.0186(8) C10 0.0458(10) 0.0522(10) 0.0408(9) -0.0013(8) -0.0077(7) -0.0247(8) C11 0.0592(11) 0.0624(12) 0.0484(10) 0.0048(9) -0.0103(9) -0.0254(10) C12 0.0766(14) 0.0850(15) 0.0443(10) 0.0137(10) -0.0148(10) -0.0428(13) C13 0.0622(12) 0.0974(17) 0.0383(10) -0.0085(11) -0.0008(9) -0.0407(12) C14 0.0567(11) 0.0750(14) 0.0516(11) -0.0100(10) -0.0012(9) -0.0246(10) C15 0.0551(11) 0.0571(11) 0.0454(10) -0.0010(8) -0.0071(8) -0.0245(9) C16 0.0392(9) 0.0470(10) 0.0521(10) 0.0029(8) -0.0061(8) -0.0224(8) C17 0.0344(8) 0.0473(10) 0.0465(9) -0.0018(8) -0.0050(7) -0.0187(7) C18 0.0445(10) 0.0474(10) 0.0537(10) -0.0029(8) -0.0008(8) -0.0224(8) C19 0.0796(16) 0.148(2) 0.0488(12) -0.0161(14) 0.0029(11) -0.0436(16) C20 0.0439(9) 0.0453(10) 0.0462(9) 0.0050(8) -0.0084(8) -0.0228(8) C21 0.0349(8) 0.0457(10) 0.0471(9) 0.0007(8) -0.0095(7) -0.0178(7) C22 0.0374(9) 0.0440(10) 0.0429(9) 0.0005(7) -0.0085(7) -0.0164(7) C23 0.0393(9) 0.0506(11) 0.0626(11) -0.0040(9) -0.0070(8) -0.0232(8) C24 0.0399(9) 0.0499(11) 0.0568(11) -0.0034(9) -0.0023(8) -0.0171(8) C25 0.0497(10) 0.0412(10) 0.0443(9) 0.0011(8) -0.0113(8) -0.0174(8) C26 0.0778(14) 0.0604(12) 0.0588(12) -0.0147(10) 0.0083(10) -0.0261(11) C27 0.0458(10) 0.0478(10) 0.0525(10) 0.0054(8) -0.0134(8) -0.0258(8) C28 0.0354(8) 0.0464(10) 0.0472(9) 0.0033(8) -0.0068(7) -0.0177(7) Cl1 0.0860(13) 0.1532(11) 0.0474(6) -0.0019(6) 0.0119(8) -0.0499(10) Cl1' 0.0860(13) 0.1532(11) 0.0474(6) -0.0019(6) 0.0119(8) -0.0499(10) O1 0.1134(13) 0.0589(10) 0.1018(13) -0.0210(9) -0.0289(11) -0.0251(9) O2 0.0783(9) 0.0493(8) 0.0663(8) 0.0008(7) -0.0165(7) -0.0241(7) O3 0.0532(8) 0.0888(10) 0.0691(9) -0.0088(7) 0.0078(6) -0.0447(7) O4 0.0503(7) 0.0882(10) 0.0445(7) -0.0037(6) -0.0026(6) -0.0301(7) O5 0.0634(8) 0.0523(8) 0.0690(8) -0.0132(7) -0.0045(7) -0.0240(6) 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' Cl Cl 0.1484 0.1585 '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 O1 C1 C2 117.6(2) . . ? O1 C1 C6 122.53(19) . . ? C2 C1 C6 119.9(2) . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 121.0(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.1(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 118.19(18) . . ? C5 C6 C7 122.01(17) . . ? C1 C6 C7 119.77(18) . . ? O2 C7 C6 120.95(17) . . ? O2 C7 C8 118.46(16) . . ? C6 C7 C8 120.49(16) . . ? C16 C8 C9 119.48(15) . . ? C16 C8 C7 116.45(14) . . ? C9 C8 C7 124.06(14) . . ? C20 C9 C8 118.21(14) . . ? C20 C9 C10 118.72(15) . . ? C8 C9 C10 122.97(15) . . ? C15 C10 C11 117.84(16) . . ? C15 C10 C9 121.26(15) . . ? C11 C10 C9 120.76(16) . . ? C12 C11 C10 121.28(18) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 119.15(19) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 121.26(17) . . ? C12 C13 Cl1 119.6(2) . . ? C14 C13 Cl1 119.1(2) . . ? C12 C13 Cl1' 105.0(11) . . ? C14 C13 Cl1' 132.7(10) . . ? C13 C14 C15 119.16(19) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C14 C15 C10 121.31(17) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? C17 C16 C8 121.14(15) . . ? C17 C16 H16 119.4 . . ? C8 C16 H16 119.4 . . ? C16 C17 C21 120.32(15) . . ? C16 C17 C18 118.19(15) . . ? C21 C17 C18 121.45(15) . . ? O3 C18 O4 124.03(16) . . ? O3 C18 C17 125.53(17) . . ? O4 C18 C17 110.44(14) . . ? O4 C19 H19A 109.5 . . ? O4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C9 C20 C21 122.98(15) . . ? C9 C20 H20 118.5 . . ? C21 C20 H20 118.5 . . ? C20 C21 C17 117.64(15) . . ? C20 C21 C22 121.01(14) . . ? C17 C21 C22 121.35(14) . . ? C23 C22 C28 117.62(15) . . ? C23 C22 C21 120.58(15) . . ? C28 C22 C21 121.79(14) . . ? C24 C23 C22 121.91(16) . . ? C24 C23 H23 119.0 . . ? C22 C23 H23 119.0 . . ? C23 C24 C25 119.46(15) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? O5 C25 C24 124.61(15) . . ? O5 C25 C27 115.77(15) . . ? C24 C25 C27 119.61(16) . . ? O5 C26 H26A 109.5 . . ? O5 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O5 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C25 120.28(16) . . ? C28 C27 H27 119.9 . . ? C25 C27 H27 119.9 . . ? C27 C28 C22 121.04(15) . . ? C27 C28 H28 119.5 . . ? C22 C28 H28 119.5 . . ? C1 O1 H1 109.5 . . ? C18 O4 C19 115.73(15) . . ? C25 O5 C26 117.19(15) . . ? 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 C1 O1 1.345(3) . ? C1 C2 1.389(3) . ? C1 C6 1.405(3) . ? C2 C3 1.357(3) . ? C2 H2 0.9300 . ? C3 C4 1.391(3) . ? C3 H3 0.9300 . ? C4 C5 1.373(3) . ? C4 H4 0.9300 . ? C5 C6 1.397(3) . ? C5 H5 0.9300 . ? C6 C7 1.468(3) . ? C7 O2 1.236(2) . ? C7 C8 1.500(2) . ? C8 C16 1.393(2) . ? C8 C9 1.407(2) . ? C9 C20 1.390(2) . ? C9 C10 1.489(2) . ? C10 C15 1.390(2) . ? C10 C11 1.392(2) . ? C11 C12 1.384(3) . ? C11 H11 0.9300 . ? C12 C13 1.371(3) . ? C12 H12 0.9300 . ? C13 C14 1.375(3) . ? C13 Cl1 1.748(2) . ? C13 Cl1' 1.784(15) . ? C14 C15 1.382(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.383(2) . ? C16 H16 0.9300 . ? C17 C21 1.406(2) . ? C17 C18 1.497(2) . ? C18 O3 1.198(2) . ? C18 O4 1.339(2) . ? C19 O4 1.445(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.391(2) . ? C20 H20 0.9300 . ? C21 C22 1.480(2) . ? C22 C23 1.389(2) . ? C22 C28 1.393(2) . ? C23 C24 1.379(2) . ? C23 H23 0.9300 . ? C24 C25 1.382(2) . ? C24 H24 0.9300 . ? C25 O5 1.362(2) . ? C25 C27 1.389(2) . ? C26 O5 1.427(2) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.374(2) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? O1 H1 0.8200 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.82 1.84 2.565(2) 146.0 .