#------------------------------------------------------------------------------ #$Date: 2016-05-14 06:25:37 +0300 (Sat, 14 May 2016) $ #$Revision: 182956 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225242.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_7225242 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 'C32 H28 O8, C2 Cl2' _chemical_formula_sum 'C34 H28 Cl2 O8' _chemical_formula_weight 635.46 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2015-10-13 _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 90 _cell_angle_beta 101.83(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 26.689(5) _cell_length_b 15.869(3) _cell_length_c 7.1690(14) _cell_measurement_temperature 100 _cell_volume 2971.8(10) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'olex2.solve (Bourhis et al., 2015)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.984 _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 0.1190 _diffrn_reflns_av_unetI/netI 0.0615 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 28750 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 30.258 _diffrn_reflns_theta_min 1.559 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.420 _exptl_crystal_description plate _exptl_crystal_F_000 1320 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.015 _refine_diff_density_max 0.361 _refine_diff_density_min -1.014 _refine_diff_density_rms 0.108 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.768 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 213 _refine_ls_number_reflns 4368 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.842 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0884 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2488 _refine_ls_wR_factor_ref 0.2597 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3590 _reflns_number_total 4368 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00929h2.cif _cod_data_source_block jono_3 _cod_original_cell_volume 2971.7(11) _cod_database_code 7225242 _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. Restrained distances Cl1_$2-C4AA 2.68 with sigma of 0.02 Cl1-C4AA 1.78 with sigma of 0.02 C4AA_$1-C1_$1 1.5 with sigma of 0.02 Cl0A_$2-C4AA = Cl1-C1_$3 = Cl1_$3-C4AA_$3 1.78 with sigma of 0.02 C4AA-Cl0A 2.68 with sigma of 0.02 Cl1-C4AA_$3 2.68 with sigma of 0.02 C1_$1-Cl1_$1 2.68 with sigma of 0.02 C6AA-C1_$3 \\sim C6AA-C4AA \\sim C4AA-C1 with sigma of 0.02 3. Rigid bond restraints Cl1, C4AA, Cl1 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 4. Others Fixed Sof: Cl1(0.5) C4AA(0.5) Cl0A(0.5) C1(0.25) C6AA(0.25) 5.a Secondary CH2 refined with riding coordinates: C5AA(H5AA,H5AB), C15(H15A,H15B) 5.b Aromatic/amide H refined with riding coordinates: C0AA(H0AA), C3AA(H3AA), C5(H5), C2AA(H2AA) 5.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C16(H16A,H16B,H16C) ; _shelx_res_file ; jono_3.res created by SHELXL-2014/7 TITL CELL 0.71073 26.6886 15.8689 7.169 90 101.829 90 ZERR 4 0.0053 0.0032 0.0014 0 0.03 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H Cl O UNIT 136 112 8 32 EQIV $1 +X,2-Y,-0.5+Z EQIV $2 +X,1-Y,-0.5+Z EQIV $3 +X,1-Y,0.5+Z DFIX 2.68 Cl1_$2 C4AA DFIX 1.78 Cl1 C4AA DFIX 1.5 C4AA_$1 C1_$1 DFIX 1.78 Cl0A_$2 C4AA Cl1 C1_$3 Cl1_$3 C4AA_$3 DFIX 2.68 C4AA Cl0A DFIX 2.68 Cl1 C4AA_$3 DFIX 2.68 C1_$1 Cl1_$1 SADI C6AA C1_$3 C6AA C4AA C4AA C1 DELU Cl1 C4AA Cl1 L.S. 10 PLAN 20 TEMP -173.15 MORE -1 BOND $H CONF fmap 2 acta 52 REM REM REM WGHT 0.100000 FVAR 0.35604 O1 4 0.697652 0.841552 1.078796 11.00000 0.03116 0.03558 = 0.02503 0.00617 0.00810 0.00619 O2 4 0.710892 0.925257 0.839897 11.00000 0.02623 0.03392 = 0.02485 0.00378 0.01042 0.00609 O3 4 0.627772 0.678324 0.977437 11.00000 0.03731 0.02977 = 0.03927 0.00886 0.01474 0.01040 O4 4 0.633284 0.770202 0.742162 11.00000 0.03438 0.02687 = 0.02563 0.00104 0.01206 0.01035 C0AA 1 0.590436 1.074005 0.931779 11.00000 0.02656 0.02594 = 0.02006 -0.00263 0.00646 0.00124 AFIX 43 H0AA 2 0.591991 1.133419 0.917738 11.00000 -1.20000 AFIX 0 C3AA 1 0.632943 1.025031 0.915947 11.00000 0.02432 0.03024 = 0.01958 -0.00323 0.00692 0.00027 AFIX 43 H3AA 2 0.662818 1.051814 0.891883 11.00000 -1.20000 AFIX 0 C1AA 1 0.632268 0.938901 0.934571 11.00000 0.02518 0.02951 = 0.01676 -0.00098 0.00639 0.00310 C4 1 0.580587 0.807670 0.954687 11.00000 0.02731 0.02724 = 0.02084 0.00102 0.00706 0.00504 C5 1 0.536438 0.772566 0.990892 11.00000 0.03031 0.02422 = 0.02685 0.00088 0.00966 0.00266 AFIX 43 H5 2 0.533879 0.713006 0.998523 11.00000 -1.20000 AFIX 0 C2AA 1 0.495327 0.822383 1.016674 11.00000 0.02724 0.02688 = 0.02666 -0.00040 0.00902 0.00078 AFIX 43 H2AA 2 0.465334 0.796062 1.040932 11.00000 -1.20000 AFIX 0 C7 1 0.497381 0.909502 1.007592 11.00000 0.02438 0.02616 = 0.01615 -0.00085 0.00637 0.00258 C8 1 0.546319 1.037930 0.967326 11.00000 0.02598 0.02595 = 0.01357 -0.00147 0.00577 0.00288 C9 1 0.543348 0.947979 0.976052 11.00000 0.02620 0.02643 = 0.01290 -0.00071 0.00534 0.00299 C10 1 0.586447 0.897065 0.954765 11.00000 0.02693 0.02619 = 0.01452 0.00012 0.00648 0.00333 C11 1 0.682780 0.894773 0.959480 11.00000 0.02726 0.02884 = 0.01852 -0.00124 0.00784 0.00278 C5AA 1 0.763113 0.894235 0.864954 11.00000 0.02770 0.03356 = 0.03333 0.00358 0.01312 0.00673 AFIX 23 H5AA 2 0.763225 0.833788 0.830879 11.00000 -1.20000 H5AB 2 0.781259 0.901012 0.999108 11.00000 -1.20000 AFIX 0 C13 1 0.788668 0.945665 0.735175 11.00000 0.03716 0.03984 = 0.04839 0.01181 0.02223 0.00898 AFIX 137 H13A 2 0.769945 0.939119 0.603317 11.00000 -1.50000 H13B 2 0.823998 0.926261 0.745713 11.00000 -1.50000 H13C 2 0.788730 1.005165 0.771838 11.00000 -1.50000 AFIX 0 C14 1 0.617082 0.745658 0.899289 11.00000 0.03051 0.02597 = 0.02565 0.00124 0.00831 0.00421 C15 1 0.670630 0.715254 0.680723 11.00000 0.03920 0.02860 = 0.03523 -0.00120 0.01542 0.01119 AFIX 23 H15A 2 0.657768 0.656591 0.667454 11.00000 -1.20000 H15B 2 0.703337 0.716062 0.775427 11.00000 -1.20000 AFIX 0 C16 1 0.678504 0.747621 0.492803 11.00000 0.06034 0.04340 = 0.04195 0.00155 0.02760 0.02051 AFIX 137 H16A 2 0.646823 0.740839 0.396961 11.00000 -1.50000 H16B 2 0.706085 0.715794 0.453649 11.00000 -1.50000 H16C 2 0.687762 0.807427 0.504723 11.00000 -1.50000 AFIX 0 CL1 3 0.565107 0.408466 0.906585 10.50000 0.09890 0.07924 = 0.15411 -0.00968 -0.00637 0.01547 C4AA 1 0.566438 0.507230 0.750041 10.50000 0.10761 CL0A 3 0.554975 0.412635 1.046310 10.50000 0.08450 0.07078 = 0.20796 0.02086 -0.01390 0.00849 C1 1 0.571606 0.498540 0.567328 10.25000 0.08222 C6AA 1 0.542892 0.504571 0.892032 10.25000 0.12579 HKLF 4 REM REM R1 = 0.0884 for 3590 Fo > 4sig(Fo) and 0.1024 for all 4368 data REM 213 parameters refined using 12 restraints END WGHT 0.1399 5.3660 REM Highest difference peak 0.361, deepest hole -1.014, 1-sigma level 0.108 Q1 1 0.5064 0.4393 0.7624 11.00000 0.05 0.36 Q2 1 0.5395 0.5076 0.8468 11.00000 0.05 0.36 Q3 1 0.5000 0.4980 0.7500 10.50000 0.05 0.35 Q4 1 0.7509 0.7319 0.7543 11.00000 0.05 0.34 Q5 1 0.8301 0.9456 0.7800 11.00000 0.05 0.34 Q6 1 0.5000 0.5694 0.7500 10.50000 0.05 0.33 Q7 1 0.7429 0.8415 1.1038 11.00000 0.05 0.32 Q8 1 0.8484 0.9674 0.6181 11.00000 0.05 0.30 Q9 1 0.6503 0.9032 0.9324 11.00000 0.05 0.30 Q10 1 0.6595 1.0552 0.9428 11.00000 0.05 0.30 Q11 1 0.7294 0.8015 1.1378 11.00000 0.05 0.30 Q12 1 0.5003 0.4843 0.8796 11.00000 0.05 0.30 Q13 1 0.7220 0.8862 1.0774 11.00000 0.05 0.30 Q14 1 0.6605 0.9376 0.9594 11.00000 0.05 0.30 Q15 1 0.5197 0.4919 0.5677 11.00000 0.05 0.30 Q16 1 0.5180 0.5527 0.7621 11.00000 0.05 0.30 Q17 1 0.5692 0.7861 1.0204 11.00000 0.05 0.29 Q18 1 0.4758 0.9351 1.0252 11.00000 0.05 0.29 Q19 1 0.6132 0.9151 0.9506 11.00000 0.05 0.29 Q20 1 0.5497 0.7973 0.9419 11.00000 0.05 0.29 ; _shelx_res_checksum 32674 _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+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy O1 O 0.69765(6) 0.84155(10) 1.0788(2) 0.0303(4) Uani 1 1 d . . . O2 O 0.71089(5) 0.92526(9) 0.8399(2) 0.0276(3) Uani 1 1 d . . . O3 O 0.62777(6) 0.67832(10) 0.9774(2) 0.0345(4) Uani 1 1 d . . . O4 O 0.63328(6) 0.77020(9) 0.7422(2) 0.0281(3) Uani 1 1 d . . . C0AA C 0.59044(7) 1.07401(12) 0.9318(3) 0.0239(4) Uani 1 1 d . . . H0AA H 0.5920 1.1334 0.9177 0.029 Uiso 1 1 calc R . . C3AA C 0.63294(7) 1.02503(13) 0.9159(3) 0.0244(4) Uani 1 1 d . . . H3AA H 0.6628 1.0518 0.8919 0.029 Uiso 1 1 calc R . . C1AA C 0.63227(7) 0.93890(12) 0.9346(3) 0.0235(4) Uani 1 1 d . . . C4 C 0.58059(8) 0.80767(12) 0.9547(3) 0.0248(4) Uani 1 1 d . . . C5 C 0.53644(8) 0.77257(12) 0.9909(3) 0.0266(4) Uani 1 1 d . . . H5 H 0.5339 0.7130 0.9985 0.032 Uiso 1 1 calc R . . C2AA C 0.49533(8) 0.82238(12) 1.0167(3) 0.0264(4) Uani 1 1 d . . . H2AA H 0.4653 0.7961 1.0409 0.032 Uiso 1 1 calc R . . C7 C 0.49738(7) 0.90950(12) 1.0076(2) 0.0219(4) Uani 1 1 d . . . C8 C 0.54632(7) 1.03793(12) 0.9673(2) 0.0216(4) Uani 1 1 d . . . C9 C 0.54335(7) 0.94798(12) 0.9761(2) 0.0217(4) Uani 1 1 d . . . C10 C 0.58645(7) 0.89707(12) 0.9548(3) 0.0222(4) Uani 1 1 d . . . C11 C 0.68278(7) 0.89477(12) 0.9595(3) 0.0244(4) Uani 1 1 d . . . C5AA C 0.76311(8) 0.89423(14) 0.8650(3) 0.0306(4) Uani 1 1 d . . . H5AA H 0.7632 0.8338 0.8309 0.037 Uiso 1 1 calc R . . H5AB H 0.7813 0.9010 0.9991 0.037 Uiso 1 1 calc R . . C13 C 0.78867(9) 0.94567(16) 0.7352(4) 0.0399(6) Uani 1 1 d . . . H13A H 0.7699 0.9391 0.6033 0.060 Uiso 1 1 calc GR . . H13B H 0.8240 0.9263 0.7457 0.060 Uiso 1 1 calc GR . . H13C H 0.7887 1.0052 0.7718 0.060 Uiso 1 1 calc GR . . C14 C 0.61708(8) 0.74566(12) 0.8993(3) 0.0270(4) Uani 1 1 d . . . C15 C 0.67063(9) 0.71525(13) 0.6807(3) 0.0332(5) Uani 1 1 d . . . H15A H 0.6578 0.6566 0.6675 0.040 Uiso 1 1 calc R . . H15B H 0.7033 0.7161 0.7754 0.040 Uiso 1 1 calc R . . C16 C 0.67850(11) 0.74762(17) 0.4928(4) 0.0461(7) Uani 1 1 d . . . H16A H 0.6468 0.7408 0.3970 0.069 Uiso 1 1 calc GR . . H16B H 0.7061 0.7158 0.4536 0.069 Uiso 1 1 calc GR . . H16C H 0.6878 0.8074 0.5047 0.069 Uiso 1 1 calc GR . . Cl1 Cl 0.56511(15) 0.4085(2) 0.9066(6) 0.1154(13) Uani 0.5 1 d D U P C4AA C 0.5664(5) 0.5072(6) 0.7500(14) 0.108(3) Uiso 0.5 1 d D U P Cl0A Cl 0.55498(13) 0.4126(2) 1.0463(8) 0.1273(15) Uani 0.5 1 d D . P C1 C 0.5716(7) 0.4985(9) 0.5673(16) 0.082(5) Uiso 0.25 1 d D . P C6AA C 0.5429(11) 0.5046(17) 0.892(2) 0.126(8) Uiso 0.25 1 d D . P 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 O1 0.0312(8) 0.0356(8) 0.0250(7) 0.0062(6) 0.0081(6) 0.0062(6) O2 0.0262(7) 0.0339(7) 0.0248(7) 0.0038(6) 0.0104(5) 0.0061(5) O3 0.0373(9) 0.0298(8) 0.0393(9) 0.0089(6) 0.0147(7) 0.0104(6) O4 0.0344(8) 0.0269(7) 0.0256(7) 0.0010(5) 0.0121(6) 0.0103(5) C0AA 0.0266(9) 0.0259(9) 0.0201(9) -0.0026(7) 0.0065(7) 0.0012(7) C3AA 0.0243(9) 0.0302(9) 0.0196(8) -0.0032(7) 0.0069(7) 0.0003(7) C1AA 0.0252(9) 0.0295(9) 0.0168(8) -0.0010(7) 0.0064(6) 0.0031(7) C4 0.0273(9) 0.0272(9) 0.0208(8) 0.0010(7) 0.0071(7) 0.0050(7) C5 0.0303(10) 0.0242(8) 0.0269(9) 0.0009(7) 0.0097(7) 0.0027(7) C2AA 0.0272(9) 0.0269(9) 0.0267(9) -0.0004(7) 0.0090(7) 0.0008(7) C7 0.0244(9) 0.0262(9) 0.0162(8) -0.0008(7) 0.0064(6) 0.0026(7) C8 0.0260(9) 0.0260(8) 0.0136(8) -0.0015(6) 0.0058(6) 0.0029(7) C9 0.0262(9) 0.0264(9) 0.0129(8) -0.0007(6) 0.0053(6) 0.0030(7) C10 0.0269(9) 0.0262(9) 0.0145(8) 0.0001(6) 0.0065(6) 0.0033(7) C11 0.0273(9) 0.0288(9) 0.0185(8) -0.0012(7) 0.0078(6) 0.0028(7) C5AA 0.0277(10) 0.0336(10) 0.0333(11) 0.0036(8) 0.0131(8) 0.0067(7) C13 0.0372(12) 0.0398(12) 0.0484(14) 0.0118(10) 0.0222(10) 0.0090(9) C14 0.0305(9) 0.0260(9) 0.0256(9) 0.0012(7) 0.0083(7) 0.0042(7) C15 0.0392(12) 0.0286(10) 0.0352(11) -0.0012(8) 0.0154(9) 0.0112(8) C16 0.0603(16) 0.0434(13) 0.0419(14) 0.0016(10) 0.0276(12) 0.0205(12) Cl1 0.099(2) 0.0792(16) 0.154(3) -0.010(2) -0.006(2) 0.0155(14) Cl0A 0.0845(19) 0.0708(16) 0.208(5) 0.021(2) -0.014(3) 0.0085(13) 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_1 _geom_angle_site_symmetry_3 C11 O2 C5AA 116.55(15) . . C14 O4 C15 115.91(15) . . C3AA C0AA H0AA 119.3 . . C8 C0AA H0AA 119.3 . . C8 C0AA C3AA 121.45(18) . . C0AA C3AA H3AA 119.4 . . C1AA C3AA C0AA 121.19(18) . . C1AA C3AA H3AA 119.4 . . C3AA C1AA C10 120.14(17) . . C3AA C1AA C11 116.59(17) . . C10 C1AA C11 122.73(17) . . C5 C4 C10 120.04(17) . . C5 C4 C14 114.44(18) . . C10 C4 C14 125.26(17) . . C4 C5 H5 119.2 . . C4 C5 C2AA 121.54(18) . . C2AA C5 H5 119.2 . . C5 C2AA H2AA 119.4 . . C7 C2AA C5 121.29(18) . . C7 C2AA H2AA 119.4 . . C2AA C7 C8 121.25(17) . 5_677 C2AA C7 C9 118.50(17) . . C9 C7 C8 120.24(17) . 5_677 C0AA C8 C7 120.95(17) . 5_677 C0AA C8 C9 118.62(16) . . C9 C8 C7 120.42(17) . 5_677 C7 C9 C8 119.33(16) . . C7 C9 C10 120.50(17) . . C8 C9 C10 120.16(17) . . C1AA C10 C4 124.02(17) . . C1AA C10 C9 118.07(17) . . C4 C10 C9 117.92(17) . . O1 C11 O2 123.98(18) . . O1 C11 C1AA 124.60(17) . . O2 C11 C1AA 111.31(16) . . O2 C5AA H5AA 110.4 . . O2 C5AA H5AB 110.4 . . O2 C5AA C13 106.55(17) . . H5AA C5AA H5AB 108.6 . . C13 C5AA H5AA 110.4 . . C13 C5AA H5AB 110.4 . . C5AA C13 H13A 109.5 . . C5AA C13 H13B 109.5 . . C5AA C13 H13C 109.5 . . H13A C13 H13B 109.5 . . H13A C13 H13C 109.5 . . H13B C13 H13C 109.5 . . O3 C14 O4 123.82(18) . . O3 C14 C4 124.17(18) . . O4 C14 C4 111.78(16) . . O4 C15 H15A 110.3 . . O4 C15 H15B 110.3 . . O4 C15 C16 107.30(17) . . H15A C15 H15B 108.5 . . C16 C15 H15A 110.3 . . C16 C15 H15B 110.3 . . C15 C16 H16A 109.5 . . C15 C16 H16B 109.5 . . C15 C16 H16C 109.5 . . H16A C16 H16B 109.5 . . H16A C16 H16C 109.5 . . H16B C16 H16C 109.5 . . Cl0A Cl1 C4AA 121.4(5) . . Cl0A Cl1 C1 52.6(5) . 6_566 Cl0A Cl1 C6AA 81.2(6) . . C1 Cl1 C4AA 72.9(5) 6_566 . C6AA Cl1 C4AA 41.8(6) . . C6AA Cl1 C1 44.3(6) . 6_566 Cl0A C4AA Cl1 164.4(7) 6_565 . C1 C4AA Cl1 119.8(9) . . C1 C4AA Cl0A 50.2(7) . 6_565 C6AA C4AA Cl1 56.7(12) . . C6AA C4AA Cl0A 126.2(14) . 6_565 C6AA C4AA C1 156.3(19) . . Cl1 Cl0A C4AA 135.2(5) . 6_566 Cl1 Cl0A C1 91.5(6) . 6_566 Cl1 Cl0A C6AA 62.4(7) . . C1 Cl0A C4AA 44.7(4) 6_566 6_566 C1 Cl0A C6AA 46.2(8) 6_566 . C6AA Cl0A C4AA 84.9(7) . 6_566 C4AA C1 Cl1 120.3(10) . 6_565 C4AA C1 Cl0A 85.0(9) . 6_565 Cl0A C1 Cl1 36.0(3) 6_565 6_565 C6AA C1 Cl1 58.8(13) 6_565 6_565 C6AA C1 C4AA 140(2) 6_565 . C6AA C1 Cl0A 80.6(14) 6_565 6_565 Cl1 C6AA Cl0A 36.4(6) . . C4AA C6AA Cl1 81.5(14) . . C4AA C6AA Cl0A 116.6(18) . . C4AA C6AA C1 118(2) . 6_566 C1 C6AA Cl1 76.9(13) 6_566 . C1 C6AA Cl0A 53.2(10) 6_566 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C11 1.210(2) . O2 C11 1.340(2) . O2 C5AA 1.454(2) . O3 C14 1.213(2) . O4 C14 1.344(2) . O4 C15 1.459(2) . C0AA H0AA 0.9500 . C0AA C3AA 1.399(3) . C0AA C8 1.379(3) . C3AA H3AA 0.9500 . C3AA C1AA 1.374(3) . C1AA C10 1.425(3) . C1AA C11 1.497(3) . C4 C5 1.375(3) . C4 C10 1.427(3) . C4 C14 1.494(3) . C5 H5 0.9500 . C5 C2AA 1.395(3) . C2AA H2AA 0.9500 . C2AA C7 1.386(3) . C7 C8 1.475(3) 5_677 C7 C9 1.429(3) . C8 C7 1.475(3) 5_677 C8 C9 1.432(3) . C9 C10 1.439(3) . C5AA H5AA 0.9900 . C5AA H5AB 0.9900 . C5AA C13 1.502(3) . C13 H13A 0.9800 . C13 H13B 0.9800 . C13 H13C 0.9800 . C15 H15A 0.9900 . C15 H15B 0.9900 . C15 C16 1.496(3) . C16 H16A 0.9800 . C16 H16B 0.9800 . C16 H16C 0.9800 . Cl1 C4AA 1.932(8) . Cl1 Cl0A 1.092(5) . Cl1 C1 1.858(12) 6_566 Cl1 C6AA 1.63(3) . C4AA Cl0A 1.913(8) 6_565 C4AA C1 1.352(11) . C4AA C6AA 1.302(16) . Cl0A C4AA 1.913(8) 6_566 Cl0A C1 1.476(15) 6_566 Cl0A C6AA 1.82(2) . C1 Cl1 1.858(12) 6_565 C1 Cl0A 1.476(15) 6_565 C1 C6AA 1.332(17) 6_565 C6AA C1 1.332(17) 6_566 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 C0AA C3AA C1AA C10 5.2(3) . . C0AA C3AA C1AA C11 -166.53(17) . . C0AA C8 C9 C7 -178.31(16) . . C0AA C8 C9 C10 2.2(2) . . C3AA C0AA C8 C7 177.19(16) . 5_677 C3AA C0AA C8 C9 -3.9(3) . . C3AA C1AA C10 C4 173.10(18) . . C3AA C1AA C10 C9 -6.7(3) . . C3AA C1AA C11 O1 132.8(2) . . C3AA C1AA C11 O2 -43.5(2) . . C4 C5 C2AA C7 -0.3(3) . . C5 C4 C10 C1AA 174.57(17) . . C5 C4 C10 C9 -5.6(3) . . C5 C4 C14 O3 -43.4(3) . . C5 C4 C14 O4 131.23(19) . . C5 C2AA C7 C8 179.29(17) . 5_677 C5 C2AA C7 C9 -1.7(3) . . C2AA C7 C9 C8 -179.64(17) . . C2AA C7 C9 C10 -0.1(3) . . C7 C8 C9 C7 0.6(3) 5_677 . C7 C8 C9 C10 -178.92(15) 5_677 . C7 C9 C10 C1AA -176.46(15) . . C7 C9 C10 C4 3.7(2) . . C8 C0AA C3AA C1AA 0.2(3) . . C8 C7 C9 C8 -0.6(3) 5_677 . C8 C7 C9 C10 178.92(15) 5_677 . C8 C9 C10 C1AA 3.0(2) . . C8 C9 C10 C4 -176.81(16) . . C10 C1AA C11 O1 -38.7(3) . . C10 C1AA C11 O2 144.95(18) . . C10 C4 C5 C2AA 4.0(3) . . C10 C4 C14 O3 142.5(2) . . C10 C4 C14 O4 -42.9(3) . . C11 O2 C5AA C13 -172.32(18) . . C11 C1AA C10 C4 -15.6(3) . . C11 C1AA C10 C9 164.52(17) . . C5AA O2 C11 O1 -3.1(3) . . C5AA O2 C11 C1AA 173.23(17) . . C14 O4 C15 C16 173.1(2) . . C14 C4 C5 C2AA -170.42(18) . . C14 C4 C10 C1AA -11.7(3) . . C14 C4 C10 C9 168.17(17) . . C15 O4 C14 O3 -7.5(3) . . C15 O4 C14 C4 177.76(17) . . Cl1 C4AA C1 Cl1 172.6(9) . 6_565 Cl1 C4AA C1 Cl0A 165.4(9) . 6_565 Cl1 C4AA C1 C6AA 96(3) . 6_565 Cl1 C4AA C6AA Cl0A 10.1(9) . . Cl1 C4AA C6AA C1 70(2) . 6_566 Cl1 Cl0A C6AA C4AA -17.0(15) . . Cl1 Cl0A C6AA C1 -122.7(15) . 6_566 C4AA Cl1 Cl0A C4AA -36.3(7) . 6_566 C4AA Cl1 Cl0A C1 -25.6(9) . 6_566 C4AA Cl1 Cl0A C6AA 11.9(11) . . C4AA Cl1 C6AA Cl0A -164.7(14) . . C4AA Cl1 C6AA C1 -121(2) . 6_566 C4AA Cl0A C6AA Cl1 148.2(7) 6_566 . C4AA Cl0A C6AA C4AA 131(2) 6_566 . C4AA Cl0A C6AA C1 25.5(13) 6_566 6_566 Cl0A Cl1 C6AA C4AA 164.7(14) . . Cl0A Cl1 C6AA C1 43.8(12) . 6_566 Cl0A C4AA C1 Cl1 7.2(7) 6_565 6_565 Cl0A C4AA C1 C6AA -69(2) 6_565 6_565 Cl0A C4AA C6AA Cl1 161.4(10) 6_565 . Cl0A C4AA C6AA Cl0A 171.4(9) 6_565 . Cl0A C4AA C6AA C1 -128.2(18) 6_565 6_566 C1 Cl1 Cl0A C4AA -10.7(9) 6_566 6_566 C1 Cl1 Cl0A C6AA 37.5(11) 6_566 . C1 Cl1 C6AA C4AA 121(2) 6_566 . C1 Cl1 C6AA Cl0A -43.8(12) 6_566 . C1 C4AA C6AA Cl1 89(4) . . C1 C4AA C6AA Cl0A 99(4) . . C1 C4AA C6AA C1 159(2) . 6_566 C1 Cl0A C6AA Cl1 122.7(15) 6_566 . C1 Cl0A C6AA C4AA 106(2) 6_566 . C6AA Cl1 Cl0A C4AA -48.1(12) . 6_566 C6AA Cl1 Cl0A C1 -37.5(11) . 6_566 C6AA C4AA C1 Cl1 98(4) . 6_565 C6AA C4AA C1 Cl0A 91(4) . 6_565 C6AA C4AA C1 C6AA 22(6) . 6_565