#------------------------------------------------------------------------------ #$Date: 2016-05-14 06:25:37 +0300 (Sat, 14 May 2016) $ #$Revision: 182956 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225240.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_7225240 loop_ _publ_author_name 'Wojciechowski, Jonathan' 'Martin, Adam David' 'Bhadbhade, Mohan' 'Webb, James' 'Thordarson, Pall' _publ_section_title ; Halogen bonding influences perylene-core twists in non-core substituted perylene tetraesters ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C6CE00929H _journal_year 2016 _chemical_formula_moiety 'C H2 Cl2, 2(C16 H14 O4)' _chemical_formula_sum 'C33 H30 Cl2 O8' _chemical_formula_weight 625.47 _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 geom _audit_creation_date 2015-11-03 _audit_creation_method ; Olex2 1.2 (compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103) ; _audit_update_record ; 2016-03-14 deposited with the CCDC. 2016-05-13 downloaded from the CCDC. ; _cell_angle_alpha 105.68(3) _cell_angle_beta 101.80(3) _cell_angle_gamma 90.67(3) _cell_formula_units_Z 2 _cell_length_a 7.4880(15) _cell_length_b 13.035(3) _cell_length_c 15.569(3) _cell_measurement_temperature 100 _cell_volume 1428.5(6) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.915 _diffrn_measured_fraction_theta_max 0.899 _diffrn_measurement_device_type 'Australian Synchrotron' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_unetI/netI 0.0453 _diffrn_reflns_Laue_measured_fraction_full 0.915 _diffrn_reflns_Laue_measured_fraction_max 0.899 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 28795 _diffrn_reflns_point_group_measured_fraction_full 0.915 _diffrn_reflns_point_group_measured_fraction_max 0.899 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 30.086 _diffrn_reflns_theta_min 1.627 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type none _exptl_crystal_colour 'yellowish orange' _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.454 _exptl_crystal_description plate _exptl_crystal_F_000 652 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.015 _refine_diff_density_max 0.982 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.083 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 392 _refine_ls_number_reflns 7572 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0505 _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^)+(0.0802P)^2^+0.6941P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1346 _refine_ls_wR_factor_ref 0.1374 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6840 _reflns_number_total 7572 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00929h2.cif _cod_data_source_block jono_5c_a _cod_original_cell_volume 1428.6(6) _cod_database_code 7225240 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C1C(H1CA,H1CB), C12B(H12A,H12B), C15B(H15A,H15B), C12A(H12C,H12D), C15A(H15C, H15D) 2.b Aromatic/amide H refined with riding coordinates: C1B(H1B), C2B(H2B), C5B(H5B), C6B(H6B), C1A(H1A), C2A(H2A), C5A(H5A), C6A(H6A) 2.c Idealised Me refined as rotating group: C13B(H13A,H13B,H13C), C16B(H16A,H16B,H16C), C13A(H13D,H13E,H13F), C16A(H16D, H16E,H16F) ; _shelx_res_file ; jono_5c_a.res created by SHELXL-2014/7 TITL Jono_5C_a.res in P-1 REM Old TITL REM SHELXT solution in P-1 REM R1 0.121, Rweak 0.007, Alpha 0.056, Orientation as input REM Formula found by SHELXT: C33 Cl2 O8 CELL 0.71073 7.488 13.035 15.569 105.678 101.8 90.667 ZERR 2 0.0015 0.0026 0.0031 0.03 0.03 0.03 LATT 1 SFAC C H Cl O UNIT 66 60 4 16 L.S. 10 PLAN 20 TEMP -173.15 BOND $H LIST 6 MORE -1 CONF fmap 2 acta 52 OMIT -8 -11 10 REM REM REM WGHT 0.080200 0.694100 FVAR 1.00305 CL1C 3 0.692504 0.509728 0.408162 11.00000 0.01888 0.03796 = 0.02558 0.01475 0.00200 0.00050 CL2C 3 0.570868 0.405719 0.213174 11.00000 0.02645 0.02313 = 0.03404 -0.00793 0.00827 -0.00142 C1C 1 0.663964 0.525684 0.296679 11.00000 0.01910 0.01381 = 0.02061 0.00343 0.00634 0.00059 AFIX 23 H1CA 2 0.581559 0.583401 0.290796 11.00000 -1.20000 H1CB 2 0.783801 0.546646 0.286558 11.00000 -1.20000 AFIX 0 O1B 4 0.306697 0.612739 0.336699 11.00000 0.01554 0.01360 = 0.02323 0.00453 0.00895 0.00394 O2B 4 0.114481 0.524258 0.390473 11.00000 0.01766 0.00855 = 0.01966 0.00189 0.00837 0.00283 O3B 4 -0.031211 0.617820 0.210801 11.00000 0.01874 0.01325 = 0.01498 -0.00091 0.00487 -0.00257 O4B 4 0.198536 0.690082 0.167832 11.00000 0.01983 0.01158 = 0.01262 -0.00222 0.00765 -0.00054 C1B 1 0.028244 0.815261 0.562618 11.00000 0.01895 0.01203 = 0.01055 0.00294 0.00472 0.00351 AFIX 43 H1B 2 0.007260 0.818681 0.621446 11.00000 -1.20000 AFIX 0 C2B 1 0.072663 0.718561 0.508262 11.00000 0.01759 0.01002 = 0.01326 0.00220 0.00434 0.00340 AFIX 43 H2B 2 0.083214 0.657856 0.531197 11.00000 -1.20000 AFIX 0 C3B 1 0.101262 0.710223 0.422037 11.00000 0.01094 0.00965 = 0.01185 0.00043 0.00225 0.00145 C4B 1 0.093063 0.794473 0.293948 11.00000 0.01170 0.01032 = 0.00896 -0.00084 0.00212 0.00086 C5B 1 0.091581 0.886172 0.266325 11.00000 0.01529 0.01207 = 0.00953 0.00095 0.00310 0.00069 AFIX 43 H5B 2 0.111614 0.882977 0.207371 11.00000 -1.20000 AFIX 0 C6B 1 0.060962 0.984187 0.323863 11.00000 0.01582 0.01028 = 0.01037 0.00174 0.00326 0.00113 AFIX 43 H6B 2 0.062324 1.046657 0.303610 11.00000 -1.20000 AFIX 0 C7B 1 0.028701 0.991769 0.409821 11.00000 0.00985 0.00908 = 0.00843 0.00005 0.00077 0.00099 C8B 1 0.014350 0.906078 0.532110 11.00000 0.01085 0.00906 = 0.00877 -0.00022 0.00144 0.00119 C9B 1 0.040907 0.899221 0.442433 11.00000 0.00913 0.00919 = 0.00845 0.00018 0.00056 0.00091 C10B 1 0.079121 0.799515 0.385111 11.00000 0.00863 0.01016 = 0.00955 -0.00010 0.00160 0.00009 C11B 1 0.185170 0.612073 0.376831 11.00000 0.01136 0.00998 = 0.01271 0.00157 0.00141 0.00193 C12B 1 0.192254 0.424282 0.353001 11.00000 0.01923 0.00780 = 0.02139 0.00129 0.00557 0.00333 AFIX 23 H12A 2 0.186890 0.376125 0.392017 11.00000 -1.20000 H12B 2 0.322250 0.438728 0.352823 11.00000 -1.20000 AFIX 0 C13B 1 0.089104 0.370646 0.257122 11.00000 0.03260 0.01625 = 0.02619 -0.00565 -0.00037 0.00667 AFIX 137 H13A 2 0.088123 0.419971 0.219416 11.00000 -1.50000 H13B 2 -0.036868 0.350548 0.258041 11.00000 -1.50000 H13C 2 0.148896 0.306498 0.231483 11.00000 -1.50000 AFIX 0 C14B 1 0.080753 0.690747 0.222148 11.00000 0.01402 0.01100 = 0.00987 0.00030 0.00240 0.00121 C15B 1 0.192113 0.591477 0.096213 11.00000 0.02773 0.01282 = 0.01569 -0.00405 0.00994 -0.00029 AFIX 23 H15A 2 0.064812 0.570300 0.061426 11.00000 -1.20000 H15B 2 0.237924 0.533436 0.122886 11.00000 -1.20000 AFIX 0 C16B 1 0.310968 0.611109 0.034340 11.00000 0.05018 0.02485 = 0.03012 -0.00373 0.02831 -0.00188 AFIX 137 H16A 2 0.268297 0.671214 0.010987 11.00000 -1.50000 H16B 2 0.304179 0.546979 -0.016935 11.00000 -1.50000 H16C 2 0.437839 0.627919 0.068671 11.00000 -1.50000 AFIX 0 O1A 4 0.422487 -0.076324 0.111733 11.00000 0.01949 0.01754 = 0.00851 0.00263 -0.00006 0.00361 O2A 4 0.677227 -0.166779 0.124401 11.00000 0.01971 0.01683 = 0.00596 0.00171 0.00406 0.00495 O3A 4 0.444377 0.169101 0.164832 11.00000 0.02591 0.01658 = 0.01011 0.00650 0.00303 0.00646 O4A 4 0.710898 0.093767 0.196822 11.00000 0.01834 0.01624 = 0.00923 0.00558 0.00494 0.00218 C1A 1 0.603235 -0.180706 0.378384 11.00000 0.01448 0.00937 = 0.00884 0.00187 0.00339 0.00178 AFIX 43 H1A 2 0.634621 -0.241941 0.398679 11.00000 -1.20000 AFIX 0 C2A 1 0.612514 -0.181243 0.289539 11.00000 0.01530 0.00982 = 0.00816 0.00059 0.00280 0.00173 AFIX 43 H2A 2 0.647795 -0.243228 0.250123 11.00000 -1.20000 AFIX 0 C3A 1 0.571197 -0.093088 0.258197 11.00000 0.01190 0.01147 = 0.00547 0.00062 0.00189 0.00024 C4A 1 0.507556 0.101339 0.295028 11.00000 0.01462 0.01184 = 0.00684 0.00296 0.00214 0.00175 C5A 1 0.462341 0.189961 0.356006 11.00000 0.01974 0.01155 = 0.01019 0.00494 0.00453 0.00409 AFIX 43 H5A 2 0.443390 0.254089 0.338550 11.00000 -1.20000 AFIX 0 C6A 1 0.443708 0.187596 0.443120 11.00000 0.01885 0.01126 = 0.00929 0.00332 0.00486 0.00459 AFIX 43 H6A 2 0.412558 0.249969 0.483760 11.00000 -1.20000 AFIX 0 C7A 1 0.470149 0.095390 0.470787 11.00000 0.01017 0.00992 = 0.00683 0.00115 0.00174 0.00106 C8A 1 0.549145 -0.092604 0.437530 11.00000 0.00959 0.00884 = 0.00677 0.00129 0.00111 0.00018 C9A 1 0.516552 0.001973 0.408924 11.00000 0.00893 0.00923 = 0.00648 0.00124 0.00138 0.00034 C10A 1 0.531765 0.003442 0.318918 11.00000 0.00999 0.00993 = 0.00709 0.00179 0.00093 0.00064 C11A 1 0.547962 -0.108303 0.157948 11.00000 0.01613 0.01005 = 0.00747 0.00108 0.00181 -0.00027 C12A 1 0.660426 -0.190578 0.026076 11.00000 0.02310 0.01640 = 0.00549 0.00148 0.00334 0.00178 AFIX 23 H12C 2 0.679512 -0.124225 0.008758 11.00000 -1.20000 H12D 2 0.537212 -0.224173 -0.006610 11.00000 -1.20000 AFIX 0 C13A 1 0.804550 -0.265961 0.002052 11.00000 0.03084 0.02498 = 0.01287 0.00271 0.00948 0.01039 AFIX 137 H13D 2 0.793885 -0.286943 -0.064266 11.00000 -1.50000 H13E 2 0.787743 -0.329640 0.022356 11.00000 -1.50000 H13F 2 0.925947 -0.230428 0.032410 11.00000 -1.50000 AFIX 0 C14A 1 0.545252 0.122761 0.210501 11.00000 0.01970 0.01027 = 0.00742 0.00192 0.00303 0.00115 C15A 1 0.759183 0.114958 0.116789 11.00000 0.02615 0.01649 = 0.01068 0.00605 0.00927 0.00240 AFIX 23 H15C 2 0.758686 0.192334 0.121960 11.00000 -1.20000 H15D 2 0.669874 0.076128 0.060713 11.00000 -1.20000 AFIX 0 C16A 1 0.947758 0.077356 0.112624 11.00000 0.02742 0.02007 = 0.01981 0.00597 0.01278 0.00213 AFIX 137 H16D 2 1.035519 0.117924 0.167549 11.00000 -1.50000 H16E 2 0.982962 0.088538 0.058389 11.00000 -1.50000 H16F 2 0.947324 0.001175 0.109230 11.00000 -1.50000 AFIX 0 HKLF 4 REM Jono_5C_a.res in P-1 REM R1 = 0.0505 for 6840 Fo > 4sig(Fo) and 0.0541 for all 7572 data REM 392 parameters refined using 0 restraints END WGHT 0.0802 0.6941 REM Highest difference peak 0.982, deepest hole -0.677, 1-sigma level 0.083 Q1 1 0.6848 0.4550 0.3795 11.00000 0.05 0.98 Q2 1 0.1281 0.6610 0.3992 11.00000 0.05 0.63 Q3 1 0.0484 0.7645 0.5327 11.00000 0.05 0.61 Q4 1 0.5381 -0.0419 0.4292 11.00000 0.05 0.60 Q5 1 0.0961 0.7425 0.2643 11.00000 0.05 0.60 Q6 1 0.5541 -0.0401 0.2899 11.00000 0.05 0.58 Q7 1 0.4816 0.0456 0.4418 11.00000 0.05 0.56 Q8 1 0.5741 -0.1408 0.4088 11.00000 0.05 0.52 Q9 1 0.0749 0.9380 0.3010 11.00000 0.05 0.51 Q10 1 0.6108 0.4242 0.1795 11.00000 0.05 0.50 Q11 1 0.0684 0.8532 0.4205 11.00000 0.05 0.49 Q12 1 0.4805 0.1458 0.3260 11.00000 0.05 0.49 Q13 1 0.0103 1.0423 0.4384 11.00000 0.05 0.45 Q14 1 0.6171 0.4776 0.2685 11.00000 0.05 0.44 Q15 1 0.0392 0.9452 0.4262 11.00000 0.05 0.43 Q16 1 0.0256 0.8592 0.5461 11.00000 0.05 0.42 Q17 1 0.0563 0.9896 0.3680 11.00000 0.05 0.41 Q18 1 0.4474 0.1403 0.4609 11.00000 0.05 0.40 Q19 1 0.5238 0.0010 0.3620 11.00000 0.05 0.38 Q20 1 0.0892 0.7912 0.3389 11.00000 0.05 0.38 ; _shelx_res_checksum 65001 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' 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 Cl1C Cl 0.69250(5) 0.50973(3) 0.40816(3) 0.02672(11) Uani 1 1 d . Cl2C Cl 0.57087(6) 0.40572(3) 0.21317(3) 0.03081(11) Uani 1 1 d . C1C C 0.6640(2) 0.52568(11) 0.29668(9) 0.0178(3) Uani 1 1 d . H1CA H 0.5816 0.5834 0.2908 0.021 Uiso 1 1 calc R H1CB H 0.7838 0.5466 0.2866 0.021 Uiso 1 1 calc R O1B O 0.30670(14) 0.61274(8) 0.33670(7) 0.0168(2) Uani 1 1 d . O2B O 0.11448(14) 0.52426(7) 0.39047(7) 0.01504(19) Uani 1 1 d . O3B O -0.03121(15) 0.61782(8) 0.21080(7) 0.0165(2) Uani 1 1 d . O4B O 0.19854(14) 0.69008(7) 0.16783(6) 0.01519(19) Uani 1 1 d . C1B C 0.02824(19) 0.81526(10) 0.56262(8) 0.0136(2) Uani 1 1 d . H1B H 0.0073 0.8187 0.6214 0.016 Uiso 1 1 calc R C2B C 0.07266(19) 0.71856(10) 0.50826(8) 0.0137(2) Uani 1 1 d . H2B H 0.0832 0.6579 0.5312 0.016 Uiso 1 1 calc R C3B C 0.10126(18) 0.71022(9) 0.42204(8) 0.0113(2) Uani 1 1 d . C4B C 0.09306(18) 0.79447(9) 0.29395(8) 0.0110(2) Uani 1 1 d . C5B C 0.09158(18) 0.88617(10) 0.26633(8) 0.0126(2) Uani 1 1 d . H5B H 0.1116 0.8830 0.2074 0.015 Uiso 1 1 calc R C6B C 0.06096(19) 0.98419(10) 0.32386(8) 0.0123(2) Uani 1 1 d . H6B H 0.0623 1.0467 0.3036 0.015 Uiso 1 1 calc R C7B C 0.02870(17) 0.99177(9) 0.40982(8) 0.0098(2) Uani 1 1 d . C8B C 0.01435(17) 0.90608(9) 0.53211(8) 0.0102(2) Uani 1 1 d . C9B C 0.04091(17) 0.89922(9) 0.44243(8) 0.0096(2) Uani 1 1 d . C10B C 0.07912(17) 0.79952(9) 0.38511(8) 0.0101(2) Uani 1 1 d . C11B C 0.18517(18) 0.61207(10) 0.37683(8) 0.0118(2) Uani 1 1 d . C12B C 0.1923(2) 0.42428(10) 0.35300(9) 0.0165(3) Uani 1 1 d . H12A H 0.1869 0.3761 0.3920 0.020 Uiso 1 1 calc R H12B H 0.3222 0.4387 0.3528 0.020 Uiso 1 1 calc R C13B C 0.0891(3) 0.37065(12) 0.25712(11) 0.0283(4) Uani 1 1 d . H13A H 0.0881 0.4200 0.2194 0.042 Uiso 1 1 calc GR H13B H -0.0369 0.3505 0.2580 0.042 Uiso 1 1 calc GR H13C H 0.1489 0.3065 0.2315 0.042 Uiso 1 1 calc GR C14B C 0.08075(18) 0.69075(10) 0.22215(8) 0.0122(2) Uani 1 1 d . C15B C 0.1921(2) 0.59148(11) 0.09621(9) 0.0196(3) Uani 1 1 d . H15A H 0.0648 0.5703 0.0614 0.023 Uiso 1 1 calc R H15B H 0.2379 0.5334 0.1229 0.023 Uiso 1 1 calc R C16B C 0.3110(3) 0.61111(14) 0.03434(13) 0.0344(4) Uani 1 1 d . H16A H 0.2683 0.6712 0.0110 0.052 Uiso 1 1 calc GR H16B H 0.3042 0.5470 -0.0169 0.052 Uiso 1 1 calc GR H16C H 0.4378 0.6279 0.0687 0.052 Uiso 1 1 calc GR O1A O 0.42249(14) -0.07632(8) 0.11173(6) 0.0158(2) Uani 1 1 d . O2A O 0.67723(14) -0.16678(8) 0.12440(6) 0.01423(19) Uani 1 1 d . O3A O 0.44438(15) 0.16910(8) 0.16483(6) 0.0171(2) Uani 1 1 d . O4A O 0.71090(14) 0.09377(7) 0.19682(6) 0.01389(19) Uani 1 1 d . C1A C 0.60324(18) -0.18071(9) 0.37838(8) 0.0109(2) Uani 1 1 d . H1A H 0.6346 -0.2419 0.3987 0.013 Uiso 1 1 calc R C2A C 0.61251(18) -0.18124(9) 0.28954(8) 0.0114(2) Uani 1 1 d . H2A H 0.6478 -0.2432 0.2501 0.014 Uiso 1 1 calc R C3A C 0.57120(17) -0.09309(9) 0.25820(7) 0.0100(2) Uani 1 1 d . C4A C 0.50756(18) 0.10134(10) 0.29503(8) 0.0110(2) Uani 1 1 d . C5A C 0.46234(19) 0.18996(10) 0.35601(8) 0.0132(2) Uani 1 1 d . H5A H 0.4434 0.2541 0.3385 0.016 Uiso 1 1 calc R C6A C 0.44371(19) 0.18760(10) 0.44312(8) 0.0127(2) Uani 1 1 d . H6A H 0.4126 0.2500 0.4838 0.015 Uiso 1 1 calc R C7A C 0.47015(17) 0.09539(9) 0.47079(7) 0.0092(2) Uani 1 1 d . C8A C 0.54915(17) -0.09260(9) 0.43753(7) 0.0087(2) Uani 1 1 d . C9A C 0.51655(16) 0.00197(9) 0.40892(7) 0.0084(2) Uani 1 1 d . C10A C 0.53177(17) 0.00344(9) 0.31892(7) 0.0093(2) Uani 1 1 d . C11A C 0.54796(18) -0.10830(9) 0.15795(8) 0.0116(2) Uani 1 1 d . C12A C 0.6604(2) -0.19058(11) 0.02608(8) 0.0153(2) Uani 1 1 d . H12C H 0.6795 -0.1242 0.0088 0.018 Uiso 1 1 calc R H12D H 0.5372 -0.2242 -0.0066 0.018 Uiso 1 1 calc R C13A C 0.8045(2) -0.26596(12) 0.00205(9) 0.0226(3) Uani 1 1 d . H13D H 0.7939 -0.2869 -0.0643 0.034 Uiso 1 1 calc GR H13E H 0.7877 -0.3296 0.0224 0.034 Uiso 1 1 calc GR H13F H 0.9259 -0.2304 0.0324 0.034 Uiso 1 1 calc GR C14A C 0.54525(19) 0.12276(10) 0.21050(8) 0.0126(2) Uani 1 1 d . C15A C 0.7592(2) 0.11496(11) 0.11679(8) 0.0165(3) Uani 1 1 d . H15C H 0.7587 0.1923 0.1220 0.020 Uiso 1 1 calc R H15D H 0.6699 0.0761 0.0607 0.020 Uiso 1 1 calc R C16A C 0.9478(2) 0.07736(12) 0.11262(10) 0.0212(3) Uani 1 1 d . H16D H 1.0355 0.1179 0.1675 0.032 Uiso 1 1 calc GR H16E H 0.9830 0.0885 0.0584 0.032 Uiso 1 1 calc GR H16F H 0.9473 0.0012 0.1092 0.032 Uiso 1 1 calc GR 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 Cl1C 0.0189(2) 0.0380(2) 0.02558(18) 0.01475(15) 0.00200(14) 0.00050(14) Cl2C 0.0264(2) 0.02313(19) 0.0340(2) -0.00793(15) 0.00827(16) -0.00142(14) C1C 0.0191(7) 0.0138(6) 0.0206(6) 0.0034(5) 0.0063(5) 0.0006(5) O1B 0.0155(5) 0.0136(4) 0.0232(5) 0.0045(3) 0.0090(4) 0.0039(3) O2B 0.0177(5) 0.0086(4) 0.0197(4) 0.0019(3) 0.0084(4) 0.0028(3) O3B 0.0187(5) 0.0133(4) 0.0150(4) -0.0009(3) 0.0049(4) -0.0026(3) O4B 0.0198(5) 0.0116(4) 0.0126(4) -0.0022(3) 0.0076(4) -0.0005(3) C1B 0.0190(7) 0.0120(5) 0.0106(5) 0.0029(4) 0.0047(4) 0.0035(4) C2B 0.0176(6) 0.0100(5) 0.0133(5) 0.0022(4) 0.0043(4) 0.0034(4) C3B 0.0109(6) 0.0097(5) 0.0118(5) 0.0004(4) 0.0023(4) 0.0014(4) C4B 0.0117(6) 0.0103(5) 0.0090(5) -0.0008(4) 0.0021(4) 0.0009(4) C5B 0.0153(6) 0.0121(5) 0.0095(5) 0.0010(4) 0.0031(4) 0.0007(4) C6B 0.0158(6) 0.0103(5) 0.0104(5) 0.0017(4) 0.0033(4) 0.0011(4) C7B 0.0098(6) 0.0091(5) 0.0084(5) 0.0000(4) 0.0008(4) 0.0010(4) C8B 0.0109(6) 0.0091(5) 0.0088(5) -0.0002(4) 0.0014(4) 0.0012(4) C9B 0.0091(6) 0.0092(5) 0.0084(5) 0.0002(4) 0.0006(4) 0.0009(4) C10B 0.0086(6) 0.0102(5) 0.0096(5) -0.0001(4) 0.0016(4) 0.0001(4) C11B 0.0114(6) 0.0100(5) 0.0127(5) 0.0016(4) 0.0014(4) 0.0019(4) C12B 0.0192(7) 0.0078(5) 0.0214(6) 0.0013(4) 0.0056(5) 0.0033(4) C13B 0.0326(9) 0.0162(6) 0.0262(7) -0.0056(5) -0.0004(6) 0.0067(6) C14B 0.0140(6) 0.0110(5) 0.0099(5) 0.0003(4) 0.0024(4) 0.0012(4) C15B 0.0277(8) 0.0128(6) 0.0157(6) -0.0040(4) 0.0099(5) -0.0003(5) C16B 0.0502(12) 0.0248(8) 0.0301(8) -0.0037(6) 0.0283(8) -0.0019(7) O1A 0.0195(5) 0.0175(4) 0.0085(4) 0.0026(3) -0.0001(3) 0.0036(4) O2A 0.0197(5) 0.0168(4) 0.0060(4) 0.0017(3) 0.0041(3) 0.0050(3) O3A 0.0259(6) 0.0166(4) 0.0101(4) 0.0065(3) 0.0030(4) 0.0065(4) O4A 0.0183(5) 0.0162(4) 0.0092(4) 0.0056(3) 0.0049(3) 0.0022(3) C1A 0.0145(6) 0.0094(5) 0.0088(5) 0.0019(4) 0.0034(4) 0.0018(4) C2A 0.0153(6) 0.0098(5) 0.0082(5) 0.0006(4) 0.0028(4) 0.0017(4) C3A 0.0119(6) 0.0115(5) 0.0055(4) 0.0006(4) 0.0019(4) 0.0002(4) C4A 0.0146(6) 0.0118(5) 0.0068(4) 0.0030(4) 0.0021(4) 0.0017(4) C5A 0.0197(7) 0.0116(5) 0.0102(5) 0.0049(4) 0.0045(4) 0.0041(4) C6A 0.0188(7) 0.0113(5) 0.0093(5) 0.0033(4) 0.0049(4) 0.0046(4) C7A 0.0102(6) 0.0099(5) 0.0068(4) 0.0012(4) 0.0017(4) 0.0011(4) C8A 0.0096(5) 0.0088(5) 0.0068(4) 0.0013(4) 0.0011(4) 0.0002(4) C9A 0.0089(5) 0.0092(5) 0.0065(4) 0.0012(4) 0.0014(4) 0.0003(4) C10A 0.0100(6) 0.0099(5) 0.0071(4) 0.0018(4) 0.0009(4) 0.0006(4) C11A 0.0161(6) 0.0100(5) 0.0075(5) 0.0011(4) 0.0018(4) -0.0003(4) C12A 0.0231(7) 0.0164(6) 0.0055(5) 0.0015(4) 0.0033(4) 0.0018(5) C13A 0.0308(8) 0.0250(7) 0.0129(6) 0.0027(5) 0.0095(5) 0.0104(6) C14A 0.0197(7) 0.0103(5) 0.0074(5) 0.0019(4) 0.0030(4) 0.0012(4) C15A 0.0262(7) 0.0165(6) 0.0107(5) 0.0060(4) 0.0093(5) 0.0024(5) C16A 0.0274(8) 0.0201(6) 0.0198(6) 0.0060(5) 0.0128(5) 0.0021(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' Cl Cl 0.1484 0.1585 '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_site_symmetry_3 Cl1C C1C H1CA 109.5 . Cl1C C1C H1CB 109.5 . Cl2C C1C Cl1C 110.79(8) . Cl2C C1C H1CA 109.5 . Cl2C C1C H1CB 109.5 . H1CA C1C H1CB 108.1 . C11B O2B C12B 116.28(11) . C14B O4B C15B 115.03(11) . C2B C1B H1B 119.4 . C8B C1B H1B 119.4 . C8B C1B C2B 121.22(11) . C1B C2B H2B 119.5 . C3B C2B C1B 120.98(11) . C3B C2B H2B 119.5 . C2B C3B C10B 120.25(11) . C2B C3B C11B 117.14(11) . C10B C3B C11B 121.82(11) . C5B C4B C10B 120.14(11) . C5B C4B C14B 117.29(11) . C10B C4B C14B 121.91(11) . C4B C5B H5B 119.5 . C4B C5B C6B 120.92(11) . C6B C5B H5B 119.5 . C5B C6B H6B 119.4 . C7B C6B C5B 121.22(11) . C7B C6B H6B 119.4 . C6B C7B C8B 120.95(11) 2_576 C6B C7B C9B 118.96(11) . C9B C7B C8B 120.08(10) 2_576 C1B C8B C7B 121.10(11) 2_576 C1B C8B C9B 118.91(11) . C9B C8B C7B 119.99(10) 2_576 C7B C9B C8B 119.92(10) . C7B C9B C10B 119.94(11) . C8B C9B C10B 120.14(11) . C3B C10B C9B 118.33(11) . C4B C10B C3B 123.33(11) . C4B C10B C9B 118.34(11) . O1B C11B O2B 124.38(12) . O1B C11B C3B 124.06(12) . O2B C11B C3B 111.48(12) . O2B C12B H12A 109.5 . O2B C12B H12B 109.5 . O2B C12B C13B 110.69(12) . H12A C12B H12B 108.1 . C13B C12B H12A 109.5 . C13B C12B H12B 109.5 . C12B C13B H13A 109.5 . C12B C13B H13B 109.5 . C12B C13B H13C 109.5 . H13A C13B H13B 109.5 . H13A C13B H13C 109.5 . H13B C13B H13C 109.5 . O3B C14B O4B 123.80(11) . O3B C14B C4B 123.57(12) . O4B C14B C4B 112.47(11) . O4B C15B H15A 110.2 . O4B C15B H15B 110.2 . O4B C15B C16B 107.40(12) . H15A C15B H15B 108.5 . C16B C15B H15A 110.2 . C16B C15B H15B 110.2 . C15B C16B H16A 109.5 . C15B C16B H16B 109.5 . C15B C16B H16C 109.5 . H16A C16B H16B 109.5 . H16A C16B H16C 109.5 . H16B C16B H16C 109.5 . C11A O2A C12A 115.71(10) . C14A O4A C15A 115.00(10) . C2A C1A H1A 119.3 . C8A C1A H1A 119.3 . C8A C1A C2A 121.33(11) . C1A C2A H2A 119.5 . C3A C2A C1A 120.98(11) . C3A C2A H2A 119.5 . C2A C3A C10A 120.03(10) . C2A C3A C11A 116.90(11) . C10A C3A C11A 122.65(10) . C5A C4A C10A 120.19(11) . C5A C4A C14A 113.80(11) . C10A C4A C14A 125.72(11) . C4A C5A H5A 119.3 . C4A C5A C6A 121.46(11) . C6A C5A H5A 119.3 . C5A C6A H6A 119.6 . C7A C6A C5A 120.80(11) . C7A C6A H6A 119.6 . C6A C7A C8A 120.97(11) 2_656 C6A C7A C9A 119.07(11) . C9A C7A C8A 119.96(10) 2_656 C1A C8A C7A 120.74(10) 2_656 C1A C8A C9A 118.82(10) . C9A C8A C7A 120.42(10) 2_656 C7A C9A C10A 120.26(10) . C8A C9A C7A 119.59(10) . C8A C9A C10A 120.14(10) . C3A C10A C9A 118.26(10) . C4A C10A C3A 123.58(11) . C4A C10A C9A 118.16(11) . O1A C11A O2A 124.11(11) . O1A C11A C3A 124.11(12) . O2A C11A C3A 111.68(10) . O2A C12A H12C 110.4 . O2A C12A H12D 110.4 . O2A C12A C13A 106.85(11) . H12C C12A H12D 108.6 . C13A C12A H12C 110.4 . C13A C12A H12D 110.4 . C12A C13A H13D 109.5 . C12A C13A H13E 109.5 . C12A C13A H13F 109.5 . H13D C13A H13E 109.5 . H13D C13A H13F 109.5 . H13E C13A H13F 109.5 . O3A C14A O4A 124.34(12) . O3A C14A C4A 123.45(13) . O4A C14A C4A 111.92(10) . O4A C15A H15C 110.2 . O4A C15A H15D 110.2 . O4A C15A C16A 107.40(11) . H15C C15A H15D 108.5 . C16A C15A H15C 110.2 . C16A C15A H15D 110.2 . C15A C16A H16D 109.5 . C15A C16A H16E 109.5 . C15A C16A H16F 109.5 . H16D C16A H16E 109.5 . H16D C16A H16F 109.5 . H16E C16A H16F 109.5 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cl1C C1C 1.7737(15) . Cl2C C1C 1.7682(16) . C1C H1CA 0.9900 . C1C H1CB 0.9900 . O1B C11B 1.2058(18) . O2B C11B 1.3412(16) . O2B C12B 1.4572(16) . O3B C14B 1.2116(17) . O4B C14B 1.3395(17) . O4B C15B 1.4490(16) . C1B H1B 0.9500 . C1B C2B 1.4014(17) . C1B C8B 1.3872(17) . C2B H2B 0.9500 . C2B C3B 1.3781(17) . C3B C10B 1.4282(17) . C3B C11B 1.4966(18) . C4B C5B 1.3748(17) . C4B C10B 1.4283(16) . C4B C14B 1.4914(17) . C5B H5B 0.9500 . C5B C6B 1.3999(17) . C6B H6B 0.9500 . C6B C7B 1.3858(17) . C7B C8B 1.4740(17) 2_576 C7B C9B 1.4269(16) . C8B C7B 1.4741(17) 2_576 C8B C9B 1.4295(16) . C9B C10B 1.4331(16) . C12B H12A 0.9900 . C12B H12B 0.9900 . C12B C13B 1.505(2) . C13B H13A 0.9800 . C13B H13B 0.9800 . C13B H13C 0.9800 . C15B H15A 0.9900 . C15B H15B 0.9900 . C15B C16B 1.505(2) . C16B H16A 0.9800 . C16B H16B 0.9800 . C16B H16C 0.9800 . O1A C11A 1.2120(16) . O2A C11A 1.3414(16) . O2A C12A 1.4557(14) . O3A C14A 1.2100(16) . O4A C14A 1.3424(17) . O4A C15A 1.4586(15) . C1A H1A 0.9500 . C1A C2A 1.3972(16) . C1A C8A 1.3866(17) . C2A H2A 0.9500 . C2A C3A 1.3798(16) . C3A C10A 1.4297(17) . C3A C11A 1.4921(16) . C4A C5A 1.3778(17) . C4A C10A 1.4262(16) . C4A C14A 1.4961(17) . C5A H5A 0.9500 . C5A C6A 1.3999(16) . C6A H6A 0.9500 . C6A C7A 1.3856(16) . C7A C8A 1.4737(16) 2_656 C7A C9A 1.4297(16) . C8A C7A 1.4738(16) 2_656 C8A C9A 1.4272(16) . C9A C10A 1.4341(16) . C12A H12C 0.9900 . C12A H12D 0.9900 . C12A C13A 1.504(2) . C13A H13D 0.9800 . C13A H13E 0.9800 . C13A H13F 0.9800 . C15A H15C 0.9900 . C15A H15D 0.9900 . C15A C16A 1.508(2) . C16A H16D 0.9800 . C16A H16E 0.9800 . C16A H16F 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_4 C1B C2B C3B C10B -2.4(2) . . C1B C2B C3B C11B 167.66(12) . . C1B C8B C9B C7B -179.51(12) . . C1B C8B C9B C10B 0.71(19) . . C2B C1B C8B C7B -178.74(12) . 2_576 C2B C1B C8B C9B 1.8(2) . . C2B C3B C10B C4B -175.18(12) . . C2B C3B C10B C9B 4.79(19) . . C2B C3B C11B O1B -135.34(14) . . C2B C3B C11B O2B 41.61(16) . . C4B C5B C6B C7B -0.9(2) . . C5B C4B C10B C3B -172.36(12) . . C5B C4B C10B C9B 7.67(19) . . C5B C4B C14B O3B -127.14(14) . . C5B C4B C14B O4B 48.52(16) . . C5B C6B C7B C8B -176.31(12) . 2_576 C5B C6B C7B C9B 4.80(19) . . C6B C7B C9B C8B 177.86(12) . . C6B C7B C9B C10B -2.36(18) . . C7B C8B C9B C7B 1.0(2) 2_576 . C7B C8B C9B C10B -178.74(11) 2_576 . C7B C9B C10B C3B 176.27(11) . . C7B C9B C10B C4B -3.75(18) . . C8B C1B C2B C3B -1.0(2) . . C8B C7B C9B C8B -1.0(2) 2_576 . C8B C7B C9B C10B 178.74(11) 2_576 . C8B C9B C10B C3B -3.95(18) . . C8B C9B C10B C4B 176.03(11) . . C10B C3B C11B O1B 34.55(19) . . C10B C3B C11B O2B -148.50(12) . . C10B C4B C5B C6B -5.5(2) . . C10B C4B C14B O3B 43.56(19) . . C10B C4B C14B O4B -140.78(12) . . C11B O2B C12B C13B -90.41(15) . . C11B C3B C10B C4B 15.24(19) . . C11B C3B C10B C9B -164.79(11) . . C12B O2B C11B O1B -0.32(18) . . C12B O2B C11B C3B -177.25(10) . . C14B O4B C15B C16B 171.53(13) . . C14B C4B C5B C6B 165.40(12) . . C14B C4B C10B C3B 17.20(19) . . C14B C4B C10B C9B -162.78(12) . . C15B O4B C14B O3B -3.96(18) . . C15B O4B C14B C4B -179.61(11) . . C1A C2A C3A C10A 4.9(2) . . C1A C2A C3A C11A -167.91(12) . . C1A C8A C9A C7A -176.70(11) . . C1A C8A C9A C10A 2.80(18) . . C2A C1A C8A C7A 176.48(12) . 2_656 C2A C1A C8A C9A -4.99(19) . . C2A C3A C10A C4A 172.88(12) . . C2A C3A C10A C9A -6.81(18) . . C2A C3A C11A O1A 133.48(14) . . C2A C3A C11A O2A -43.08(16) . . C4A C5A C6A C7A -0.1(2) . . C5A C4A C10A C3A 177.31(12) . . C5A C4A C10A C9A -2.99(19) . . C5A C4A C14A O3A -49.51(18) . . C5A C4A C14A O4A 124.55(13) . . C5A C6A C7A C8A 179.94(12) . 2_656 C5A C6A C7A C9A -0.1(2) . . C6A C7A C9A C8A 178.26(12) . . C6A C7A C9A C10A -1.24(18) . . C7A C8A C9A C7A 1.84(19) 2_656 . C7A C8A C9A C10A -178.67(11) 2_656 . C7A C9A C10A C3A -177.52(11) . . C7A C9A C10A C4A 2.77(18) . . C8A C1A C2A C3A 1.2(2) . . C8A C7A C9A C8A -1.83(19) 2_656 . C8A C7A C9A C10A 178.68(11) 2_656 . C8A C9A C10A C3A 2.99(18) . . C8A C9A C10A C4A -176.72(11) . . C10A C3A C11A O1A -39.1(2) . . C10A C3A C11A O2A 144.36(12) . . C10A C4A C5A C6A 1.7(2) . . C10A C4A C14A O3A 136.75(14) . . C10A C4A C14A O4A -49.19(17) . . C11A O2A C12A C13A -173.86(12) . . C11A C3A C10A C4A -14.8(2) . . C11A C3A C10A C9A 165.53(12) . . C12A O2A C11A O1A 0.43(18) . . C12A O2A C11A C3A 176.98(10) . . C14A O4A C15A C16A -179.94(11) . . C14A C4A C5A C6A -172.42(12) . . C14A C4A C10A C3A -9.3(2) . . C14A C4A C10A C9A 170.37(12) . . C15A O4A C14A O3A -4.44(18) . . C15A O4A C14A C4A -178.44(10) . .