# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-ea-190K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-ea, 190 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Cl3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Cl3 O5' _chemical_formula_weight 672.05 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.6558(4) _cell_length_b 13.4048(7) _cell_length_c 14.5814(11) _cell_angle_alpha 111.503(6) _cell_angle_beta 92.122(5) _cell_angle_gamma 90.099(4) _cell_volume 1754.51(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4209 _cell_measurement_temperature 190(2) _cell_measurement_theta_max 29.1049 _cell_measurement_theta_min 3.7026 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92451 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 708 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_unetI/netI 0.0661 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 15807 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.17 _diffrn_reflns_theta_min 3.71 _diffrn_ambient_temperature 190(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.841 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0169445000 _diffrn_orient_matrix_UB_12 -0.0099746000 _diffrn_orient_matrix_UB_13 0.0428162000 _diffrn_orient_matrix_UB_21 -0.0010276000 _diffrn_orient_matrix_UB_22 0.0559955000 _diffrn_orient_matrix_UB_23 0.0272622000 _diffrn_orient_matrix_UB_31 -0.0715325000 _diffrn_orient_matrix_UB_32 0.0005959000 _diffrn_orient_matrix_UB_33 -0.0127112000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5359 _reflns_number_total 7972 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.476 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.100 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 7972 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1393 _refine_ls_R_factor_gt 0.1086 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1550P)^2^+4.6518P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3176 _refine_ls_wR_factor_ref 0.3354 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 O2B-C15 \\sim O2A-C15 with sigma of 0.02 3. Others Sof(O2A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)= Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C14A)=Sof(H14C)= Sof(H14D)=Sof(O3A)=Sof(C22A)=Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)= Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(Cl3A)=1-FVAR(1) Sof(Cl3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)= Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C3B)=Sof(C5B)=Sof(C14B)=Sof(H14A)=Sof(H14B)= Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C4B)= Sof(C24B)=Sof(H24B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21A(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C14A(H14C,H14D), C21B(H21C,H21D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.98036(17) 0.11177(13) 0.96479(10) 0.0574(4) Uani 1 1 d . . . Cl1 Cl 1.71796(14) 0.03680(14) 0.12620(11) 0.0604(5) Uani 1 1 d . . . Cl3B Cl 0.5277(15) 0.9359(12) 0.3190(12) 0.089(4) Uani 0.618(14) 1 d A 1 . O2A O 0.9525(15) 0.2901(9) 0.6575(9) 0.042(3) Uiso 0.382(14) 1 d A 2 . C9 C 1.3179(5) 0.1028(4) 0.1741(3) 0.0352(10) Uani 1 1 d . . . H9 H 1.2312 0.0780 0.1404 0.042 Uiso 1 1 calc . . R O3B O 0.6952(9) 0.5355(6) 0.3586(5) 0.037(2) Uiso 0.618(14) 1 d A 1 . C8 C 1.3241(4) 0.1867(4) 0.2652(3) 0.0332(9) Uani 1 1 d . . . C15 C 0.9322(5) 0.2447(4) 0.7224(4) 0.0399(11) Uani 1 1 d . . . C19 C 0.8380(5) 0.1481(4) 0.8168(4) 0.0442(12) Uani 1 1 d . . . H19 H 0.7634 0.1098 0.8301 0.053 Uiso 1 1 calc A . R C18 C 0.9614(5) 0.1656(4) 0.8726(4) 0.0406(11) Uani 1 1 d A . . C10 C 1.4405(5) 0.0557(4) 0.1328(4) 0.0405(11) Uani 1 1 d . . . H10 H 1.4378 -0.0036 0.0718 0.049 Uiso 1 1 calc . . R C12 C 1.5721(5) 0.1801(4) 0.2702(4) 0.0421(11) Uani 1 1 d . . . H12 H 1.6592 0.2071 0.3023 0.050 Uiso 1 1 calc . . R C13 C 1.4513(5) 0.2246(4) 0.3120(4) 0.0412(11) Uani 1 1 d . . . H13 H 1.4549 0.2823 0.3741 0.049 Uiso 1 1 calc . . R C20 C 0.8255(5) 0.1875(4) 0.7413(4) 0.0438(12) Uani 1 1 d A . . H20 H 0.7419 0.1750 0.7019 0.053 Uiso 1 1 calc . . R C22B C 0.6642(12) 0.6300(9) 0.3505(8) 0.038(3) Uiso 0.618(14) 1 d A 1 . C27B C 0.6991(11) 0.7270(8) 0.4239(9) 0.040(3) Uiso 0.618(14) 1 d A 1 . H27B H 0.7519 0.7295 0.4810 0.048 Uiso 0.618(14) 1 calc A 1 R C23B C 0.5951(11) 0.6237(10) 0.2657(9) 0.044(3) Uiso 0.618(14) 1 d A 1 . H23B H 0.5779 0.5561 0.2144 0.052 Uiso 0.618(14) 1 calc A 1 R C11 C 1.5649(5) 0.0951(4) 0.1805(4) 0.0402(11) Uani 1 1 d . . . C16 C 1.0545(6) 0.2631(4) 0.7795(4) 0.0470(12) Uani 1 1 d A . . H16 H 1.1284 0.3024 0.7665 0.056 Uiso 1 1 calc . . R C25B C 0.5806(8) 0.8131(8) 0.3283(7) 0.037(2) Uiso 0.618(14) 1 d A 1 . C26B C 0.6560(9) 0.8210(7) 0.4132(8) 0.039(2) Uiso 0.618(14) 1 d A 1 . H26B H 0.6778 0.8890 0.4629 0.046 Uiso 0.618(14) 1 calc A 1 R O1 O 1.2100(3) 0.2362(3) 0.3145(2) 0.0380(8) Uani 1 1 d A . . C2 C 0.9419(5) 0.2271(3) 0.4219(3) 0.0326(9) Uani 1 1 d . . . C1 C 0.9745(4) 0.2639(4) 0.3463(3) 0.0339(9) Uani 1 1 d A . . C28 C 0.9978(5) 0.1217(4) 0.4237(4) 0.0366(10) Uani 1 1 d A . . H28A H 1.0889 0.1085 0.3927 0.044 Uiso 1 1 calc . . R H28B H 1.0126 0.1279 0.4932 0.044 Uiso 1 1 calc . . R C21A C 0.8360(19) 0.5483(12) 0.4380(11) 0.037(3) Uiso 0.382(14) 1 d A 2 . H21A H 0.8021 0.5897 0.5042 0.045 Uiso 0.382(14) 1 calc A 2 R H21B H 0.9197 0.5852 0.4280 0.045 Uiso 0.382(14) 1 calc A 2 R C7 C 1.0738(4) 0.2006(4) 0.2709(4) 0.0359(10) Uani 1 1 d . . . H7A H 1.0610 0.1228 0.2559 0.043 Uiso 1 1 calc A . R H7B H 1.0597 0.2145 0.2091 0.043 Uiso 1 1 calc . . R C32 C 0.9550(5) 0.4006(4) 0.2632(4) 0.0413(11) Uani 1 1 d A . . H32A H 1.0489 0.3775 0.2399 0.050 Uiso 1 1 calc . . R H32B H 0.9537 0.4799 0.2880 0.050 Uiso 1 1 calc . . R C6 C 0.9243(5) 0.3629(4) 0.3462(3) 0.0337(9) Uani 1 1 d . . . C33 C 0.8481(7) 0.3549(5) 0.1764(4) 0.0563(15) Uani 1 1 d . . . H33A H 0.8724 0.3788 0.1230 0.084 Uiso 1 1 calc A . GR H33B H 0.7556 0.3806 0.1986 0.084 Uiso 1 1 calc . . GR H33C H 0.8481 0.2764 0.1524 0.084 Uiso 1 1 calc . . GR C3B C 0.8377(11) 0.2816(10) 0.4887(9) 0.024(2) Uani 0.618(14) 1 d A 1 . C29 C 0.9015(6) 0.0267(4) 0.3704(5) 0.0488(13) Uani 1 1 d . . . H29A H 0.8927 0.0164 0.3004 0.073 Uiso 1 1 calc A . GR H29B H 0.8101 0.0405 0.3992 0.073 Uiso 1 1 calc . . GR H29C H 0.9397 -0.0379 0.3774 0.073 Uiso 1 1 calc . . GR C5B C 0.8277(14) 0.4190(13) 0.4187(12) 0.028(2) Uani 0.618(14) 1 d A 1 . C14B C 0.8056(10) 0.2447(7) 0.5713(6) 0.030(2) Uiso 0.618(14) 1 d A 1 . H14A H 0.7171 0.2753 0.6005 0.037 Uiso 0.618(14) 1 calc A 1 R H14B H 0.7970 0.1655 0.5463 0.037 Uiso 0.618(14) 1 calc A 1 R C4A C 0.8412(16) 0.4005(10) 0.5102(11) 0.030(3) Uani 0.382(14) 1 d A 2 . C30A C 0.7641(15) 0.4705(10) 0.5983(10) 0.042(4) Uani 0.382(14) 1 d A 2 . H30A H 0.7813 0.4458 0.6539 0.050 Uiso 0.382(14) 1 calc A 2 R H30B H 0.7990 0.5454 0.6191 0.050 Uiso 0.382(14) 1 calc A 2 R C30B C 0.6594(10) 0.4260(8) 0.5509(7) 0.038(2) Uani 0.618(14) 1 d A 1 . H30C H 0.5984 0.3678 0.5538 0.046 Uiso 0.618(14) 1 calc A 1 R H30D H 0.6045 0.4675 0.5189 0.046 Uiso 0.618(14) 1 calc A 1 R C31B C 0.6985(9) 0.5009(7) 0.6576(7) 0.046(2) Uani 0.618(14) 1 d A 1 . H31A H 0.7311 0.5702 0.6577 0.069 Uiso 0.618(14) 1 calc A 1 GR H31B H 0.7722 0.4684 0.6849 0.069 Uiso 0.618(14) 1 calc A 1 GR H31C H 0.6170 0.5116 0.6981 0.069 Uiso 0.618(14) 1 calc A 1 GR C17 C 1.0694(6) 0.2244(4) 0.8558(4) 0.0506(13) Uani 1 1 d . . . H17 H 1.1524 0.2381 0.8958 0.061 Uiso 1 1 calc A . R C4B C 0.7768(11) 0.3756(7) 0.4863(6) 0.0297(18) Uani 0.618(14) 1 d A 1 . C24B C 0.5503(11) 0.7159(8) 0.2548(9) 0.050(3) Uiso 0.618(14) 1 d A 1 . H24B H 0.4988 0.7125 0.1969 0.059 Uiso 0.618(14) 1 calc A 1 R C31A C 0.614(2) 0.467(2) 0.5748(19) 0.064(6) Uani 0.382(14) 1 d A 2 . H31D H 0.5969 0.4868 0.5170 0.096 Uiso 0.382(14) 1 calc A 2 GR H31E H 0.5667 0.5175 0.6312 0.096 Uiso 0.382(14) 1 calc A 2 GR H31F H 0.5772 0.3943 0.5605 0.096 Uiso 0.382(14) 1 calc A 2 GR C3A C 0.8838(18) 0.297(2) 0.5031(18) 0.033(4) Uani 0.382(14) 1 d A 2 . C5A C 0.872(2) 0.436(2) 0.431(2) 0.038(5) Uani 0.382(14) 1 d A 2 . C14A C 0.842(2) 0.2589(15) 0.5881(14) 0.047(5) Uiso 0.382(14) 1 d A 2 . H14C H 0.7556 0.2935 0.6176 0.057 Uiso 0.382(14) 1 calc A 2 R H14D H 0.8282 0.1802 0.5630 0.057 Uiso 0.382(14) 1 calc A 2 R C21B C 0.7921(11) 0.5346(7) 0.4330(6) 0.033(2) Uiso 0.618(14) 1 d A 1 . H21C H 0.7529 0.5705 0.4986 0.040 Uiso 0.618(14) 1 calc A 1 R H21D H 0.8773 0.5744 0.4299 0.040 Uiso 0.618(14) 1 calc A 1 R O2B O 0.9166(9) 0.2804(6) 0.6437(5) 0.0375(19) Uiso 0.618(14) 1 d A 1 . O3A O 0.7293(16) 0.5424(11) 0.3628(10) 0.047(4) Uiso 0.382(14) 1 d A 2 . C22A C 0.6748(16) 0.6435(12) 0.3693(10) 0.027(4) Uiso 0.382(14) 1 d A 2 . C27A C 0.6985(15) 0.7397(9) 0.4476(12) 0.028(4) Uiso 0.382(14) 1 d A 2 . H27A H 0.7508 0.7403 0.5043 0.033 Uiso 0.382(14) 1 calc A 2 R C26A C 0.6470(12) 0.8358(10) 0.4448(11) 0.030(3) Uiso 0.382(14) 1 d A 2 . H26A H 0.6631 0.9007 0.4997 0.036 Uiso 0.382(14) 1 calc A 2 R C25A C 0.5723(10) 0.8366(9) 0.3620(9) 0.021(2) Uiso 0.382(14) 1 d A 2 . C24A C 0.5479(12) 0.7436(10) 0.2818(10) 0.026(3) Uiso 0.382(14) 1 d A 2 . H24A H 0.5012 0.7449 0.2238 0.031 Uiso 0.382(14) 1 calc A 2 R C23A C 0.5938(15) 0.6462(12) 0.2874(12) 0.031(4) Uiso 0.382(14) 1 d A 2 . H23A H 0.5697 0.5808 0.2350 0.038 Uiso 0.382(14) 1 calc A 2 R Cl3A Cl 0.511(3) 0.9514(19) 0.3506(17) 0.070(4) Uani 0.382(14) 1 d A 2 . 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 Cl2 0.0719(9) 0.0630(9) 0.0469(7) 0.0308(7) 0.0083(6) 0.0103(7) Cl1 0.0367(6) 0.0824(11) 0.0596(9) 0.0221(8) 0.0119(6) 0.0162(6) Cl3B 0.049(3) 0.076(7) 0.181(12) 0.098(8) -0.030(6) -0.011(4) C9 0.030(2) 0.037(2) 0.039(2) 0.014(2) 0.0019(17) -0.0017(18) C8 0.031(2) 0.033(2) 0.037(2) 0.0135(19) 0.0015(17) -0.0005(17) C15 0.053(3) 0.028(2) 0.044(3) 0.018(2) 0.018(2) 0.009(2) C19 0.038(2) 0.050(3) 0.056(3) 0.032(3) 0.010(2) 0.004(2) C18 0.048(3) 0.038(2) 0.041(2) 0.019(2) 0.014(2) 0.011(2) C10 0.040(2) 0.043(3) 0.036(2) 0.012(2) 0.0075(19) 0.002(2) C12 0.032(2) 0.048(3) 0.046(3) 0.018(2) -0.004(2) -0.006(2) C13 0.036(2) 0.041(3) 0.039(2) 0.007(2) -0.0037(19) -0.002(2) C20 0.038(2) 0.045(3) 0.060(3) 0.033(3) 0.009(2) 0.006(2) C11 0.032(2) 0.049(3) 0.045(3) 0.022(2) 0.0089(19) 0.007(2) C16 0.055(3) 0.037(3) 0.049(3) 0.015(2) 0.015(2) -0.009(2) O1 0.0297(15) 0.0343(17) 0.0415(17) 0.0038(14) 0.0019(13) -0.0009(13) C2 0.037(2) 0.023(2) 0.039(2) 0.0136(18) 0.0028(18) 0.0008(17) C1 0.031(2) 0.037(2) 0.034(2) 0.0136(19) 0.0004(17) 0.0000(18) C28 0.036(2) 0.033(2) 0.044(2) 0.018(2) 0.0037(19) 0.0104(18) C7 0.028(2) 0.037(2) 0.041(2) 0.013(2) -0.0002(18) -0.0011(17) C32 0.040(2) 0.046(3) 0.045(3) 0.026(2) 0.003(2) -0.002(2) C6 0.037(2) 0.032(2) 0.037(2) 0.0185(19) 0.0045(18) 0.0008(18) C33 0.061(3) 0.068(4) 0.040(3) 0.020(3) -0.005(2) 0.008(3) C3B 0.019(5) 0.023(5) 0.031(5) 0.012(4) 0.003(4) 0.001(4) C29 0.053(3) 0.025(2) 0.065(3) 0.012(2) 0.007(3) 0.004(2) C5B 0.035(7) 0.020(6) 0.032(5) 0.014(5) 0.002(5) 0.001(5) C4A 0.027(7) 0.021(6) 0.040(7) 0.009(5) 0.001(5) -0.011(5) C30A 0.057(8) 0.031(6) 0.040(7) 0.017(6) 0.009(6) 0.002(6) C30B 0.033(5) 0.033(5) 0.049(5) 0.015(4) -0.001(4) 0.006(3) C31B 0.048(5) 0.039(4) 0.046(5) 0.009(4) 0.012(4) 0.004(4) C17 0.056(3) 0.045(3) 0.046(3) 0.011(2) 0.002(2) -0.007(2) C4B 0.033(4) 0.020(4) 0.035(4) 0.009(3) 0.001(3) -0.002(3) C31A 0.047(11) 0.070(14) 0.098(17) 0.057(13) 0.012(10) 0.002(9) C3A 0.016(8) 0.035(9) 0.048(9) 0.019(7) -0.007(7) -0.011(7) C5A 0.039(13) 0.023(9) 0.048(11) 0.010(8) 0.000(10) -0.010(9) Cl3A 0.054(6) 0.049(3) 0.124(9) 0.055(5) -0.014(5) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl2 C18 1.747(5) . ? Cl1 C11 1.749(5) . ? Cl3B C25B 1.775(17) . ? O2A C15 1.320(11) . ? O2A C14A 1.39(2) . ? C9 H9 0.9500 . ? C9 C8 1.390(6) . ? C9 C10 1.393(6) . ? O3B C22B 1.348(14) . ? O3B C21B 1.409(12) . ? C8 C13 1.383(6) . ? C8 O1 1.372(5) . ? C15 C20 1.377(7) . ? C15 C16 1.387(8) . ? C15 O2B 1.400(8) . ? C19 H19 0.9500 . ? C19 C18 1.387(7) . ? C19 C20 1.388(7) . ? C18 C17 1.389(8) . ? C10 H10 0.9500 . ? C10 C11 1.369(7) . ? C12 H12 0.9500 . ? C12 C13 1.370(7) . ? C12 C11 1.384(7) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C22B C27B 1.379(11) . ? C22B C23B 1.357(11) . ? C27B H27B 0.9500 . ? C27B C26B 1.388(10) . ? C23B H23B 0.9500 . ? C23B C24B 1.371(11) . ? C16 H16 0.9500 . ? C16 C17 1.392(8) . ? C25B C26B 1.382(10) . ? C25B C24B 1.372(10) . ? C26B H26B 0.9500 . ? O1 C7 1.440(5) . ? C2 C1 1.408(6) . ? C2 C28 1.523(6) . ? C2 C3B 1.431(12) . ? C2 C3A 1.35(3) . ? C1 C7 1.498(6) . ? C1 C6 1.413(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.519(7) . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C21A C5A 1.51(3) . ? C21A O3A 1.46(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.511(6) . ? C32 C33 1.542(8) . ? C6 C5B 1.430(17) . ? C6 C5A 1.38(3) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.501(15) . ? C3B C4B 1.403(14) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.417(17) . ? C5B C21B 1.528(18) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C14B O2B 1.427(11) . ? C4A C30A 1.509(18) . ? C4A C3A 1.42(3) . ? C4A C5A 1.44(3) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.48(2) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.543(13) . ? C30B C4B 1.498(14) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C24B H24B 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C3A C14A 1.57(3) . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? O3A C22A 1.43(2) . ? C22A C27A 1.387(13) . ? C22A C23A 1.414(13) . ? C27A H27A 0.9500 . ? C27A C26A 1.395(12) . ? C26A H26A 0.9500 . ? C26A C25A 1.387(12) . ? C25A C24A 1.373(12) . ? C25A Cl3A 1.71(3) . ? C24A H24A 0.9500 . ? C24A C23A 1.409(12) . ? C23A H23A 0.9500 . ? 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 C15 O2A C14A 107.3(12) . . ? C8 C9 H9 120.4 . . ? C8 C9 C10 119.2(4) . . ? C10 C9 H9 120.4 . . ? C22B O3B C21B 118.8(8) . . ? C13 C8 C9 119.9(4) . . ? O1 C8 C9 124.2(4) . . ? O1 C8 C13 115.9(4) . . ? O2A C15 C20 135.3(8) . . ? O2A C15 C16 104.9(8) . . ? O2A C15 O2B 16.2(6) . . ? C20 C15 C16 119.7(5) . . ? C20 C15 O2B 119.1(6) . . ? C16 C15 O2B 121.1(6) . . ? C18 C19 H19 120.6 . . ? C18 C19 C20 118.9(5) . . ? C20 C19 H19 120.6 . . ? C19 C18 Cl2 119.1(4) . . ? C19 C18 C17 121.0(5) . . ? C17 C18 Cl2 119.9(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 C9 119.7(5) . . ? C11 C10 H10 120.2 . . ? C13 C12 H12 120.6 . . ? C13 C12 C11 118.8(4) . . ? C11 C12 H12 120.6 . . ? C8 C13 H13 119.5 . . ? C12 C13 C8 121.0(5) . . ? C12 C13 H13 119.5 . . ? C15 C20 C19 121.0(5) . . ? C15 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? O3B C22B C27B 122.2(9) . . ? O3B C22B C23B 115.8(9) . . ? C23B C22B C27B 122.0(10) . . ? C22B C27B H27B 120.5 . . ? C22B C27B C26B 119.1(9) . . ? C26B C27B H27B 120.5 . . ? C22B C23B H23B 120.3 . . ? C22B C23B C24B 119.4(11) . . ? C24B C23B H23B 120.3 . . ? C10 C11 Cl1 119.0(4) . . ? C10 C11 C12 121.5(4) . . ? C12 C11 Cl1 119.5(4) . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.2(5) . . ? C17 C16 H16 119.9 . . ? C26B C25B Cl3B 116.2(8) . . ? C24B C25B Cl3B 122.0(8) . . ? C24B C25B C26B 121.8(8) . . ? C27B C26B H26B 120.9 . . ? C25B C26B C27B 118.2(9) . . ? C25B C26B H26B 120.9 . . ? C8 O1 C7 119.2(3) . . ? C1 C2 C28 121.2(4) . . ? C1 C2 C3B 118.6(6) . . ? C3B C2 C28 119.5(6) . . ? C3A C2 C1 118.1(11) . . ? C3A C2 C28 119.4(11) . . ? C3A C2 C3B 20.2(6) . . ? C2 C1 C7 118.4(4) . . ? C2 C1 C6 120.8(4) . . ? C6 C1 C7 120.6(4) . . ? C2 C28 H28A 109.0 . . ? C2 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C29 C28 C2 112.9(4) . . ? C29 C28 H28A 109.0 . . ? C29 C28 H28B 109.0 . . ? H21A C21A H21B 108.3 . . ? C5A C21A H21A 109.8 . . ? C5A C21A H21B 109.8 . . ? O3A C21A H21A 109.8 . . ? O3A C21A H21B 109.8 . . ? O3A C21A C5A 109.3(15) . . ? O1 C7 C1 105.6(4) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 108.0 . . ? C6 C32 H32A 109.4 . . ? C6 C32 H32B 109.4 . . ? C6 C32 C33 111.4(4) . . ? C33 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C1 C6 C32 120.8(4) . . ? C1 C6 C5B 118.3(7) . . ? C5B C6 C32 120.3(7) . . ? C5A C6 C1 119.9(14) . . ? C5A C6 C32 117.9(14) . . ? C5A C6 C5B 19.6(8) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 118.8(9) . . ? C4B C3B C2 121.8(9) . . ? C4B C3B C14B 118.9(9) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 119.4(10) . . ? C4B C5B C6 121.8(12) . . ? C4B C5B C21B 118.3(12) . . ? C3B C14B H14A 110.2 . . ? C3B C14B H14B 110.2 . . ? H14A C14B H14B 108.5 . . ? O2B C14B C3B 107.6(7) . . ? O2B C14B H14A 110.2 . . ? O2B C14B H14B 110.2 . . ? C3A C4A C30A 120.3(14) . . ? C3A C4A C5A 118.6(18) . . ? C5A C4A C30A 121.1(16) . . ? C4A C30A H30A 109.4 . . ? C4A C30A H30B 109.4 . . ? H30A C30A H30B 108.0 . . ? C31A C30A C4A 111.0(17) . . ? C31A C30A H30A 109.4 . . ? C31A C30A H30B 109.4 . . ? H30C C30B H30D 107.3 . . ? C31B C30B H30C 108.1 . . ? C31B C30B H30D 108.1 . . ? C4B C30B H30C 108.1 . . ? C4B C30B H30D 108.1 . . ? C4B C30B C31B 116.7(9) . . ? C18 C17 C16 119.1(5) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C3B C4B C5B 117.6(10) . . ? C3B C4B C30B 120.9(8) . . ? C5B C4B C30B 121.5(9) . . ? C23B C24B C25B 119.4(10) . . ? C23B C24B H24B 120.3 . . ? C25B C24B H24B 120.3 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 122.6(19) . . ? C2 C3A C14A 120.0(19) . . ? C4A C3A C14A 116.9(18) . . ? C6 C5A C21A 121(2) . . ? C6 C5A C4A 118(2) . . ? C4A C5A C21A 121(2) . . ? O2A C14A C3A 105.4(14) . . ? O2A C14A H14C 110.7 . . ? O2A C14A H14D 110.7 . . ? C3A C14A H14C 110.7 . . ? C3A C14A H14D 110.7 . . ? H14C C14A H14D 108.8 . . ? O3B C21B C5B 109.7(8) . . ? O3B C21B H21C 109.7 . . ? O3B C21B H21D 109.7 . . ? C5B C21B H21C 109.7 . . ? C5B C21B H21D 109.7 . . ? H21C C21B H21D 108.2 . . ? C15 O2B C14B 122.7(7) . . ? C22A O3A C21A 114.6(12) . . ? C27A C22A O3A 125.4(12) . . ? C27A C22A C23A 117.3(13) . . ? C23A C22A O3A 117.2(12) . . ? C22A C27A H27A 119.4 . . ? C22A C27A C26A 121.2(13) . . ? C26A C27A H27A 119.4 . . ? C27A C26A H26A 119.9 . . ? C25A C26A C27A 120.1(12) . . ? C25A C26A H26A 119.9 . . ? C26A C25A Cl3A 123.1(12) . . ? C24A C25A C26A 120.9(10) . . ? C24A C25A Cl3A 115.9(12) . . ? C25A C24A H24A 120.7 . . ? C25A C24A C23A 118.5(11) . . ? C23A C24A H24A 120.7 . . ? C22A C23A H23A 119.2 . . ? C24A C23A C22A 121.6(13) . . ? C24A C23A H23A 119.2 . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C18 C17 C16 177.5(4) . . . . ? Cl3B C25B C26B C27B 179.7(9) . . . . ? Cl3B C25B C24B C23B 179.4(10) . . . . ? O2A C15 C20 C19 178.9(9) . . . . ? O2A C15 C16 C17 -179.3(7) . . . . ? O2A C15 O2B C14B 171(3) . . . . ? C9 C8 C13 C12 -0.5(8) . . . . ? C9 C8 O1 C7 0.1(7) . . . . ? C9 C10 C11 Cl1 -178.6(4) . . . . ? C9 C10 C11 C12 1.1(8) . . . . ? O3B C22B C27B C26B -175.9(10) . . . . ? O3B C22B C23B C24B 175.0(10) . . . . ? C8 C9 C10 C11 -2.5(7) . . . . ? C8 O1 C7 C1 175.3(4) . . . . ? C15 O2A C14A C3A -170.0(13) . . . . ? C15 C16 C17 C18 1.2(8) . . . . ? C19 C18 C17 C16 -2.1(8) . . . . ? C18 C19 C20 C15 -1.0(8) . . . . ? C10 C9 C8 C13 2.2(7) . . . . ? C10 C9 C8 O1 -177.4(4) . . . . ? C13 C8 O1 C7 -179.4(4) . . . . ? C13 C12 C11 Cl1 -179.7(4) . . . . ? C13 C12 C11 C10 0.6(8) . . . . ? C20 C15 C16 C17 -0.2(8) . . . . ? C20 C15 O2B C14B -11.3(9) . . . . ? C20 C19 C18 Cl2 -177.6(4) . . . . ? C20 C19 C18 C17 2.0(8) . . . . ? C22B O3B C21B C5B -171.4(10) . . . . ? C22B C27B C26B C25B -0.6(15) . . . . ? C22B C23B C24B C25B 2.4(17) . . . . ? C27B C22B C23B C24B -4.4(18) . . . . ? C23B C22B C27B C26B 3.5(18) . . . . ? C11 C12 C13 C8 -0.9(8) . . . . ? C16 C15 C20 C19 0.1(8) . . . . ? C16 C15 O2B C14B 166.8(6) . . . . ? C26B C25B C24B C23B 0.4(15) . . . . ? O1 C8 C13 C12 179.1(5) . . . . ? C2 C1 C7 O1 -83.7(5) . . . . ? C2 C1 C6 C32 -177.8(4) . . . . ? C2 C1 C6 C5B -6.6(9) . . . . ? C2 C1 C6 C5A 15.7(12) . . . . ? C2 C3B C14B O2B 74.7(10) . . . . ? C2 C3B C4B C5B -3.6(14) . . . . ? C2 C3B C4B C30B 174.6(9) . . . . ? C2 C3A C14A O2A 96.7(15) . . . . ? C1 C2 C28 C29 -91.1(5) . . . . ? C1 C2 C3B C14B -178.2(7) . . . . ? C1 C2 C3B C4B -5.8(12) . . . . ? C1 C2 C3A C4A 7.0(17) . . . . ? C1 C2 C3A C14A 178.5(11) . . . . ? C1 C6 C5B C4B -3.2(13) . . . . ? C1 C6 C5B C21B 168.8(8) . . . . ? C1 C6 C5A C21A 171.3(12) . . . . ? C1 C6 C5A C4A -13.7(19) . . . . ? C28 C2 C1 C7 -4.1(6) . . . . ? C28 C2 C1 C6 -178.7(4) . . . . ? C28 C2 C3B C14B 11.4(11) . . . . ? C28 C2 C3B C4B -176.3(7) . . . . ? C28 C2 C3A C4A 174.0(11) . . . . ? C28 C2 C3A C14A -14.6(17) . . . . ? C21A O3A C22A C27A -11(2) . . . . ? C21A O3A C22A C23A 166.8(14) . . . . ? C7 C1 C6 C32 7.7(7) . . . . ? C7 C1 C6 C5B 178.9(7) . . . . ? C7 C1 C6 C5A -158.8(10) . . . . ? C32 C6 C5B C4B 168.1(8) . . . . ? C32 C6 C5B C21B -20.0(13) . . . . ? C32 C6 C5A C21A 5(2) . . . . ? C32 C6 C5A C4A 179.5(11) . . . . ? C6 C1 C7 O1 90.9(5) . . . . ? C6 C5B C4B C3B 8.1(15) . . . . ? C6 C5B C4B C30B -170.1(10) . . . . ? C6 C5B C21B O3B 79.5(11) . . . . ? C33 C32 C6 C1 86.0(6) . . . . ? C33 C32 C6 C5B -85.0(8) . . . . ? C33 C32 C6 C5A -107.3(11) . . . . ? C3B C2 C1 C7 -174.4(6) . . . . ? C3B C2 C1 C6 11.0(8) . . . . ? C3B C2 C28 C29 79.0(7) . . . . ? C3B C2 C3A C4A -90(4) . . . . ? C3B C2 C3A C14A 81(4) . . . . ? C3B C14B O2B C15 -168.8(7) . . . . ? C5B C6 C5A C21A -98(6) . . . . ? C5B C6 C5A C4A 77(5) . . . . ? C14B C3B C4B C5B 168.8(9) . . . . ? C14B C3B C4B C30B -13.0(14) . . . . ? C4A C3A C14A O2A -91.3(16) . . . . ? C30A C4A C3A C2 173.9(14) . . . . ? C30A C4A C3A C14A 2(2) . . . . ? C30A C4A C5A C21A 4(2) . . . . ? C30A C4A C5A C6 -170.7(15) . . . . ? C31B C30B C4B C3B 83.7(11) . . . . ? C31B C30B C4B C5B -98.2(12) . . . . ? C4B C3B C14B O2B -97.9(9) . . . . ? C4B C5B C21B O3B -108.3(11) . . . . ? C24B C25B C26B C27B -1.2(14) . . . . ? C3A C2 C1 C7 162.6(9) . . . . ? C3A C2 C1 C6 -12.0(10) . . . . ? C3A C2 C28 C29 102.3(9) . . . . ? C3A C2 C3B C14B -84(4) . . . . ? C3A C2 C3B C4B 88(4) . . . . ? C3A C4A C30A C31A -100.2(16) . . . . ? C3A C4A C5A C21A -176.4(15) . . . . ? C3A C4A C5A C6 9(2) . . . . ? C5A C21A O3A C22A 172.9(17) . . . . ? C5A C6 C5B C4B -103(6) . . . . ? C5A C6 C5B C21B 69(5) . . . . ? C5A C4A C30A C31A 79.1(18) . . . . ? C5A C4A C3A C2 -5(2) . . . . ? C5A C4A C3A C14A -177.1(15) . . . . ? C14A O2A C15 C20 -8.6(15) . . . . ? C14A O2A C15 C16 170.4(10) . . . . ? C14A O2A C15 O2B -6(2) . . . . ? C21B O3B C22B C27B -14.6(16) . . . . ? C21B O3B C22B C23B 166.0(10) . . . . ? C21B C5B C4B C3B -163.9(9) . . . . ? C21B C5B C4B C30B 17.9(15) . . . . ? O2B C15 C20 C19 178.2(5) . . . . ? O2B C15 C16 C17 -178.2(5) . . . . ? O3A C21A C5A C6 61(2) . . . . ? O3A C21A C5A C4A -114.1(18) . . . . ? O3A C22A C27A C26A 176.3(14) . . . . ? O3A C22A C23A C24A -173.0(14) . . . . ? C22A C27A C26A C25A -1(2) . . . . ? C27A C22A C23A C24A 5(2) . . . . ? C27A C26A C25A C24A -0.1(19) . . . . ? C27A C26A C25A Cl3A -177.4(14) . . . . ? C26A C25A C24A C23A 3.5(18) . . . . ? C25A C24A C23A C22A -6(2) . . . . ? C23A C22A C27A C26A -1(2) . . . . ? Cl3A C25A C24A C23A -179.0(13) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.007 0.000 0.500 358 37 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962425' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-ea-226K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-ea, 226 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Cl3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Cl3 O5' _chemical_formula_weight 672.05 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.6879(5) _cell_length_b 13.4280(8) _cell_length_c 14.6215(11) _cell_angle_alpha 111.346(6) _cell_angle_beta 92.071(5) _cell_angle_gamma 90.031(5) _cell_volume 1770.3(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3927 _cell_measurement_temperature 226(2) _cell_measurement_theta_max 29.0759 _cell_measurement_theta_min 3.7047 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83037 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 708 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_unetI/netI 0.0737 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 15791 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.14 _diffrn_reflns_theta_min 3.71 _diffrn_ambient_temperature 226(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.842 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0168980000 _diffrn_orient_matrix_UB_12 -0.0100298000 _diffrn_orient_matrix_UB_13 0.0426896000 _diffrn_orient_matrix_UB_21 -0.0010584000 _diffrn_orient_matrix_UB_22 0.0558209000 _diffrn_orient_matrix_UB_23 0.0271179000 _diffrn_orient_matrix_UB_31 -0.0712880000 _diffrn_orient_matrix_UB_32 0.0006911000 _diffrn_orient_matrix_UB_33 -0.0126116000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4857 _reflns_number_total 8040 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.540 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.089 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 8040 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1476 _refine_ls_R_factor_gt 0.1069 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1555P)^2^+3.0567P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3096 _refine_ls_wR_factor_ref 0.3326 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 O2B-C15 \\sim O2A-C15 with sigma of 0.02 3. Others Sof(O2A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)= Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C14A)=Sof(H14C)= Sof(H14D)=Sof(O3A)=Sof(C22A)=Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)= Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(Cl3A)=1-FVAR(1) Sof(Cl3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)= Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C3B)=Sof(C5B)=Sof(C14B)=Sof(H14A)=Sof(H14B)= Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C4B)= Sof(C24B)=Sof(H24B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21A(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C14A(H14C,H14D), C21B(H21C,H21D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.97860(18) 0.11162(14) 0.96359(11) 0.0693(5) Uani 1 1 d . . . Cl1 Cl 1.71683(14) 0.03749(15) 0.12664(12) 0.0711(5) Uani 1 1 d . . . Cl3B Cl 0.5304(17) 0.9365(11) 0.3203(15) 0.115(6) Uani 0.611(14) 1 d A 1 . O2A O 0.9518(14) 0.2870(9) 0.6554(8) 0.045(3) Uiso 0.389(14) 1 d A 2 . C9 C 1.3180(5) 0.1035(4) 0.1746(3) 0.0417(10) Uani 1 1 d . . . H9 H 1.2325 0.0793 0.1414 0.050 Uiso 1 1 calc . . R O3B O 0.6967(9) 0.5355(6) 0.3604(6) 0.044(2) Uiso 0.611(14) 1 d A 1 . C8 C 1.3245(4) 0.1864(4) 0.2648(3) 0.0389(9) Uani 1 1 d . . . C15 C 0.9319(5) 0.2439(4) 0.7213(4) 0.0452(11) Uani 1 1 d . . . C19 C 0.8382(5) 0.1472(5) 0.8159(4) 0.0543(13) Uani 1 1 d . . . H19 H 0.7650 0.1088 0.8288 0.065 Uiso 1 1 calc A . R C18 C 0.9612(5) 0.1655(4) 0.8716(4) 0.0482(11) Uani 1 1 d A . . C10 C 1.4407(5) 0.0565(4) 0.1337(4) 0.0466(11) Uani 1 1 d . . . H10 H 1.4384 -0.0021 0.0738 0.056 Uiso 1 1 calc . . R C12 C 1.5716(5) 0.1797(4) 0.2700(4) 0.0485(11) Uani 1 1 d . . . H12 H 1.6576 0.2054 0.3019 0.058 Uiso 1 1 calc . . R C13 C 1.4506(5) 0.2251(4) 0.3116(4) 0.0504(12) Uani 1 1 d . . . H13 H 1.4539 0.2828 0.3722 0.061 Uiso 1 1 calc . . R C20 C 0.8262(5) 0.1872(4) 0.7407(4) 0.0504(12) Uani 1 1 d A . . H20 H 0.7437 0.1751 0.7022 0.060 Uiso 1 1 calc . . R C22B C 0.6667(12) 0.6285(9) 0.3502(8) 0.044(3) Uiso 0.611(14) 1 d A 1 . C27B C 0.6978(13) 0.7257(8) 0.4237(9) 0.049(4) Uiso 0.611(14) 1 d A 1 . H27B H 0.7465 0.7286 0.4814 0.059 Uiso 0.611(14) 1 calc A 1 R C23B C 0.5977(11) 0.6226(10) 0.2658(9) 0.052(3) Uiso 0.611(14) 1 d A 1 . H23B H 0.5825 0.5561 0.2146 0.063 Uiso 0.611(14) 1 calc A 1 R C11 C 1.5643(5) 0.0962(4) 0.1812(4) 0.0462(11) Uani 1 1 d . . . C16 C 1.0538(6) 0.2626(4) 0.7784(4) 0.0561(13) Uani 1 1 d A . . H16 H 1.1269 0.3014 0.7660 0.067 Uiso 1 1 calc . . R C25B C 0.5817(8) 0.8121(8) 0.3260(8) 0.043(2) Uiso 0.611(14) 1 d A 1 . C26B C 0.6564(10) 0.8193(8) 0.4114(8) 0.048(2) Uiso 0.611(14) 1 d A 1 . H26B H 0.6784 0.8864 0.4600 0.058 Uiso 0.611(14) 1 calc A 1 R O1 O 1.2100(3) 0.2365(3) 0.3146(2) 0.0454(8) Uani 1 1 d A . . C2 C 0.9418(4) 0.2271(3) 0.4215(3) 0.0371(9) Uani 1 1 d . . . C1 C 0.9752(4) 0.2641(4) 0.3466(3) 0.0385(9) Uani 1 1 d A . . C28 C 0.9975(5) 0.1214(4) 0.4233(4) 0.0434(10) Uani 1 1 d A . . H28A H 1.0872 0.1081 0.3923 0.052 Uiso 1 1 calc . . R H28B H 1.0122 0.1272 0.4917 0.052 Uiso 1 1 calc . . R C21A C 0.8342(17) 0.5471(11) 0.4368(10) 0.036(3) Uiso 0.389(14) 1 d A 2 . H21A H 0.7994 0.5882 0.5017 0.043 Uiso 0.389(14) 1 calc A 2 R H21B H 0.9170 0.5839 0.4277 0.043 Uiso 0.389(14) 1 calc A 2 R C7 C 1.0743(4) 0.2010(4) 0.2713(3) 0.0399(10) Uani 1 1 d . . . H7A H 1.0618 0.1242 0.2567 0.048 Uiso 1 1 calc A . R H7B H 1.0602 0.2148 0.2103 0.048 Uiso 1 1 calc . . R C32 C 0.9569(5) 0.4010(4) 0.2638(4) 0.0481(11) Uani 1 1 d A . . H32A H 1.0495 0.3780 0.2408 0.058 Uiso 1 1 calc . . R H32B H 0.9559 0.4793 0.2883 0.058 Uiso 1 1 calc . . R C6 C 0.9251(5) 0.3629(4) 0.3463(3) 0.0396(10) Uani 1 1 d . . . C33 C 0.8498(7) 0.3557(6) 0.1774(4) 0.0680(16) Uani 1 1 d . . . H33A H 0.8730 0.3801 0.1250 0.102 Uiso 1 1 calc A . GR H33B H 0.7585 0.3803 0.1997 0.102 Uiso 1 1 calc . . GR H33C H 0.8508 0.2781 0.1532 0.102 Uiso 1 1 calc . . GR C3B C 0.8378(11) 0.2813(11) 0.4902(11) 0.029(2) Uani 0.611(14) 1 d A 1 . C29 C 0.9012(6) 0.0277(4) 0.3705(4) 0.0564(13) Uani 1 1 d . . . H29A H 0.8964 0.0154 0.3008 0.085 Uiso 1 1 calc A . GR H29B H 0.8097 0.0434 0.3966 0.085 Uiso 1 1 calc . . GR H29C H 0.9356 -0.0356 0.3803 0.085 Uiso 1 1 calc . . GR C5B C 0.8282(14) 0.4194(15) 0.4175(14) 0.034(3) Uani 0.611(14) 1 d A 1 . C14B C 0.8024(10) 0.2435(7) 0.5684(6) 0.037(2) Uiso 0.611(14) 1 d A 1 . H14A H 0.7953 0.1653 0.5432 0.044 Uiso 0.611(14) 1 calc A 1 R H14B H 0.7141 0.2730 0.5959 0.044 Uiso 0.611(14) 1 calc A 1 R C4A C 0.8409(16) 0.3993(10) 0.5092(9) 0.032(3) Uani 0.389(14) 1 d A 2 . C30A C 0.7633(14) 0.4704(10) 0.5997(10) 0.045(4) Uani 0.389(14) 1 d A 2 . H30A H 0.7795 0.4447 0.6538 0.054 Uiso 0.389(14) 1 calc A 2 R H30B H 0.7986 0.5440 0.6209 0.054 Uiso 0.389(14) 1 calc A 2 R C30B C 0.6583(11) 0.4271(7) 0.5506(7) 0.042(2) Uani 0.611(14) 1 d A 1 . H30C H 0.6059 0.4694 0.5195 0.051 Uiso 0.611(14) 1 calc A 1 R H30D H 0.5966 0.3703 0.5528 0.051 Uiso 0.611(14) 1 calc A 1 R C31B C 0.6978(10) 0.4988(7) 0.6554(7) 0.054(3) Uani 0.611(14) 1 d A 1 . H31A H 0.7372 0.5653 0.6556 0.081 Uiso 0.611(14) 1 calc A 1 GR H31B H 0.7652 0.4632 0.6830 0.081 Uiso 0.611(14) 1 calc A 1 GR H31C H 0.6162 0.5138 0.6945 0.081 Uiso 0.611(14) 1 calc A 1 GR C17 C 1.0669(6) 0.2230(4) 0.8548(4) 0.0561(13) Uani 1 1 d . . . H17 H 1.1485 0.2361 0.8944 0.067 Uiso 1 1 calc A . R C4B C 0.7784(11) 0.3751(7) 0.4855(7) 0.0361(19) Uani 0.611(14) 1 d A 1 . C24B C 0.5506(11) 0.7144(8) 0.2561(9) 0.057(3) Uiso 0.611(14) 1 d A 1 . H24B H 0.4959 0.7100 0.2003 0.069 Uiso 0.611(14) 1 calc A 1 R C31A C 0.6123(18) 0.4680(19) 0.5756(19) 0.077(6) Uani 0.389(14) 1 d A 2 . H31D H 0.5977 0.4689 0.5099 0.115 Uiso 0.389(14) 1 calc A 2 GR H31E H 0.5698 0.5302 0.6226 0.115 Uiso 0.389(14) 1 calc A 2 GR H31F H 0.5711 0.4035 0.5787 0.115 Uiso 0.389(14) 1 calc A 2 GR C3A C 0.8838(19) 0.296(2) 0.500(2) 0.039(5) Uani 0.389(14) 1 d A 2 . C5A C 0.872(2) 0.435(2) 0.432(2) 0.035(4) Uani 0.389(14) 1 d A 2 . C14A C 0.8413(18) 0.2570(11) 0.5870(11) 0.038(3) Uiso 0.389(14) 1 d A 2 . H14C H 0.7563 0.2915 0.6165 0.046 Uiso 0.389(14) 1 calc A 2 R H14D H 0.8268 0.1793 0.5621 0.046 Uiso 0.389(14) 1 calc A 2 R C21B C 0.7908(11) 0.5342(8) 0.4328(7) 0.042(2) Uiso 0.611(14) 1 d A 1 . H21C H 0.7511 0.5682 0.4974 0.050 Uiso 0.611(14) 1 calc A 1 R H21D H 0.8741 0.5746 0.4308 0.050 Uiso 0.611(14) 1 calc A 1 R O2B O 0.9149(10) 0.2812(6) 0.6433(5) 0.045(2) Uiso 0.611(14) 1 d A 1 . O3A O 0.7291(15) 0.5425(11) 0.3611(10) 0.052(4) Uiso 0.389(14) 1 d A 2 . C22A C 0.6724(15) 0.6436(12) 0.3688(10) 0.031(4) Uiso 0.389(14) 1 d A 2 . C27A C 0.7011(16) 0.7386(9) 0.4448(12) 0.031(4) Uiso 0.389(14) 1 d A 2 . H27A H 0.7578 0.7390 0.4985 0.038 Uiso 0.389(14) 1 calc A 2 R C26A C 0.6482(12) 0.8332(10) 0.4436(10) 0.033(3) Uiso 0.389(14) 1 d A 2 . H26A H 0.6624 0.8966 0.4986 0.040 Uiso 0.389(14) 1 calc A 2 R C25A C 0.5747(10) 0.8352(8) 0.3623(8) 0.024(2) Uiso 0.389(14) 1 d A 2 . C24A C 0.5492(12) 0.7429(9) 0.2820(9) 0.031(3) Uiso 0.389(14) 1 d A 2 . H24A H 0.5041 0.7451 0.2248 0.037 Uiso 0.389(14) 1 calc A 2 R C23A C 0.5921(14) 0.6457(11) 0.2876(11) 0.034(4) Uiso 0.389(14) 1 d A 2 . H23A H 0.5669 0.5812 0.2365 0.041 Uiso 0.389(14) 1 calc A 2 R Cl3A Cl 0.510(2) 0.9467(13) 0.346(2) 0.081(4) Uani 0.389(14) 1 d A 2 . 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 Cl2 0.0873(11) 0.0772(10) 0.0554(8) 0.0378(7) 0.0100(7) 0.0116(8) Cl1 0.0441(7) 0.0960(12) 0.0698(9) 0.0251(8) 0.0152(6) 0.0189(7) Cl3B 0.056(4) 0.107(7) 0.238(15) 0.135(9) -0.034(6) -0.012(4) C9 0.034(2) 0.046(3) 0.044(2) 0.016(2) 0.0020(18) -0.0040(18) C8 0.036(2) 0.037(2) 0.043(2) 0.0137(19) 0.0042(18) -0.0006(17) C15 0.055(3) 0.036(2) 0.051(3) 0.023(2) 0.020(2) 0.007(2) C19 0.046(3) 0.066(3) 0.067(3) 0.043(3) 0.017(2) 0.007(2) C18 0.058(3) 0.047(3) 0.044(2) 0.020(2) 0.014(2) 0.013(2) C10 0.047(3) 0.051(3) 0.041(2) 0.015(2) 0.009(2) 0.002(2) C12 0.038(2) 0.054(3) 0.052(3) 0.019(2) -0.004(2) -0.003(2) C13 0.045(3) 0.052(3) 0.045(3) 0.006(2) -0.006(2) -0.004(2) C20 0.045(3) 0.055(3) 0.067(3) 0.040(3) 0.011(2) 0.007(2) C11 0.036(2) 0.057(3) 0.051(3) 0.025(2) 0.009(2) 0.008(2) C16 0.064(3) 0.043(3) 0.060(3) 0.016(2) 0.017(3) -0.011(2) O1 0.0322(15) 0.0432(18) 0.0499(18) 0.0040(14) 0.0022(13) -0.0019(13) C2 0.040(2) 0.028(2) 0.047(2) 0.0163(18) 0.0054(19) 0.0019(17) C1 0.036(2) 0.038(2) 0.042(2) 0.0142(18) 0.0032(18) -0.0003(17) C28 0.041(2) 0.037(2) 0.054(3) 0.019(2) 0.004(2) 0.0121(19) C7 0.035(2) 0.040(2) 0.043(2) 0.0131(19) 0.0017(18) -0.0003(18) C32 0.046(3) 0.055(3) 0.053(3) 0.030(2) 0.008(2) 0.000(2) C6 0.041(2) 0.039(2) 0.043(2) 0.0195(19) 0.0062(19) 0.0018(18) C33 0.077(4) 0.083(4) 0.044(3) 0.024(3) 0.000(3) 0.010(3) C3B 0.021(5) 0.026(5) 0.043(5) 0.016(4) 0.013(5) 0.001(4) C29 0.064(3) 0.030(2) 0.072(3) 0.015(2) 0.006(3) 0.004(2) C5B 0.033(7) 0.028(6) 0.044(7) 0.017(5) 0.002(6) 0.001(5) C4A 0.033(7) 0.032(6) 0.032(6) 0.013(5) -0.004(5) -0.012(5) C30A 0.059(8) 0.034(6) 0.046(7) 0.018(5) 0.008(6) 0.000(6) C30B 0.042(5) 0.034(4) 0.053(5) 0.017(4) 0.005(4) 0.009(4) C31B 0.058(5) 0.051(5) 0.048(5) 0.009(4) 0.014(4) 0.004(4) C17 0.059(3) 0.054(3) 0.053(3) 0.017(2) 0.000(2) -0.008(2) C4B 0.034(5) 0.029(4) 0.043(4) 0.009(3) 0.004(4) -0.002(4) C31A 0.039(9) 0.077(14) 0.133(19) 0.058(14) 0.034(10) 0.017(8) C3A 0.026(10) 0.045(10) 0.055(9) 0.029(8) 0.010(9) -0.010(8) C5A 0.032(11) 0.033(10) 0.046(10) 0.022(8) -0.010(9) -0.003(8) Cl3A 0.056(6) 0.052(4) 0.157(8) 0.066(4) -0.024(5) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl2 C18 1.748(5) . ? Cl1 C11 1.752(5) . ? Cl3B C25B 1.773(16) . ? O2A C15 1.311(10) . ? O2A C14A 1.391(19) . ? C9 H9 0.9400 . ? C9 C8 1.381(6) . ? C9 C10 1.396(6) . ? O3B C22B 1.342(14) . ? O3B C21B 1.377(13) . ? C8 C13 1.382(6) . ? C8 O1 1.384(5) . ? C15 C20 1.374(7) . ? C15 C16 1.390(8) . ? C15 O2B 1.407(8) . ? C19 H19 0.9400 . ? C19 C18 1.388(8) . ? C19 C20 1.390(7) . ? C18 C17 1.364(8) . ? C10 H10 0.9400 . ? C10 C11 1.368(7) . ? C12 H12 0.9400 . ? C12 C13 1.378(7) . ? C12 C11 1.372(7) . ? C13 H13 0.9400 . ? C20 H20 0.9400 . ? C22B C27B 1.380(12) . ? C22B C23B 1.358(11) . ? C27B H27B 0.9400 . ? C27B C26B 1.390(10) . ? C23B H23B 0.9400 . ? C23B C24B 1.368(11) . ? C16 H16 0.9400 . ? C16 C17 1.402(8) . ? C25B C26B 1.392(10) . ? C25B C24B 1.363(11) . ? C26B H26B 0.9400 . ? O1 C7 1.441(5) . ? C2 C1 1.405(6) . ? C2 C28 1.528(6) . ? C2 C3B 1.447(14) . ? C2 C3A 1.32(3) . ? C1 C7 1.499(6) . ? C1 C6 1.413(6) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 C29 1.513(7) . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A C5A 1.52(3) . ? C21A O3A 1.46(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 C6 1.512(6) . ? C32 C33 1.545(8) . ? C6 C5B 1.428(19) . ? C6 C5A 1.40(3) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C3B C14B 1.461(17) . ? C3B C4B 1.408(16) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C5B C4B 1.43(2) . ? C5B C21B 1.52(2) . ? C14B H14A 0.9800 . ? C14B H14B 0.9800 . ? C14B O2B 1.467(11) . ? C4A C30A 1.543(18) . ? C4A C3A 1.40(3) . ? C4A C5A 1.42(3) . ? C30A H30A 0.9800 . ? C30A H30B 0.9800 . ? C30A C31A 1.49(2) . ? C30B H30C 0.9800 . ? C30B H30D 0.9800 . ? C30B C31B 1.517(13) . ? C30B C4B 1.531(14) . ? C31B H31A 0.9700 . ? C31B H31B 0.9700 . ? C31B H31C 0.9700 . ? C17 H17 0.9400 . ? C24B H24B 0.9400 . ? C31A H31D 0.9700 . ? C31A H31E 0.9700 . ? C31A H31F 0.9700 . ? C3A C14A 1.62(3) . ? C14A H14C 0.9800 . ? C14A H14D 0.9800 . ? C21B H21C 0.9800 . ? C21B H21D 0.9800 . ? O3A C22A 1.43(2) . ? C22A C27A 1.373(13) . ? C22A C23A 1.404(12) . ? C27A H27A 0.9400 . ? C27A C26A 1.376(12) . ? C26A H26A 0.9400 . ? C26A C25A 1.373(12) . ? C25A C24A 1.376(12) . ? C25A Cl3A 1.72(2) . ? C24A H24A 0.9400 . ? C24A C23A 1.400(12) . ? C23A H23A 0.9400 . ? 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 C15 O2A C14A 108.0(10) . . ? C8 C9 H9 120.6 . . ? C8 C9 C10 118.8(4) . . ? C10 C9 H9 120.6 . . ? C22B O3B C21B 119.5(8) . . ? C9 C8 C13 120.6(4) . . ? C9 C8 O1 124.1(4) . . ? C13 C8 O1 115.3(4) . . ? O2A C15 C20 135.1(8) . . ? O2A C15 C16 105.5(7) . . ? O2A C15 O2B 15.9(6) . . ? C20 C15 C16 119.4(5) . . ? C20 C15 O2B 119.2(6) . . ? C16 C15 O2B 121.3(5) . . ? C18 C19 H19 120.9 . . ? C18 C19 C20 118.1(5) . . ? C20 C19 H19 120.9 . . ? C19 C18 Cl2 118.2(4) . . ? C17 C18 Cl2 120.4(4) . . ? C17 C18 C19 121.4(5) . . ? C9 C10 H10 120.2 . . ? C11 C10 C9 119.6(4) . . ? C11 C10 H10 120.2 . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C11 C12 C13 118.7(4) . . ? C8 C13 H13 119.8 . . ? C12 C13 C8 120.4(4) . . ? C12 C13 H13 119.8 . . ? C15 C20 C19 121.7(5) . . ? C15 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? O3B C22B C27B 121.9(9) . . ? O3B C22B C23B 116.7(9) . . ? C23B C22B C27B 121.3(11) . . ? C22B C27B H27B 120.4 . . ? C22B C27B C26B 119.3(10) . . ? C26B C27B H27B 120.4 . . ? C22B C23B H23B 120.4 . . ? C22B C23B C24B 119.3(11) . . ? C24B C23B H23B 120.4 . . ? C10 C11 Cl1 118.6(4) . . ? C10 C11 C12 121.9(4) . . ? C12 C11 Cl1 119.5(4) . . ? C15 C16 H16 120.3 . . ? C15 C16 C17 119.4(5) . . ? C17 C16 H16 120.3 . . ? C26B C25B Cl3B 114.7(9) . . ? C24B C25B Cl3B 125.2(9) . . ? C24B C25B C26B 120.0(8) . . ? C27B C26B C25B 118.9(9) . . ? C27B C26B H26B 120.6 . . ? C25B C26B H26B 120.6 . . ? C8 O1 C7 119.1(3) . . ? C1 C2 C28 121.1(4) . . ? C1 C2 C3B 119.7(7) . . ? C3B C2 C28 118.6(7) . . ? C3A C2 C1 117.0(12) . . ? C3A C2 C28 120.7(12) . . ? C3A C2 C3B 19.4(9) . . ? C2 C1 C7 118.5(4) . . ? C2 C1 C6 120.8(4) . . ? C6 C1 C7 120.5(4) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? H28A C28 H28B 107.8 . . ? C29 C28 C2 112.7(4) . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? H21A C21A H21B 108.0 . . ? C5A C21A H21A 109.4 . . ? C5A C21A H21B 109.4 . . ? O3A C21A H21A 109.4 . . ? O3A C21A H21B 109.4 . . ? O3A C21A C5A 111.1(13) . . ? O1 C7 C1 105.5(3) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 108.1 . . ? C6 C32 H32A 109.5 . . ? C6 C32 H32B 109.5 . . ? C6 C32 C33 110.8(4) . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? C1 C6 C32 120.8(4) . . ? C1 C6 C5B 118.9(9) . . ? C5B C6 C32 119.7(9) . . ? C5A C6 C1 118.9(13) . . ? C5A C6 C32 118.8(13) . . ? C5A C6 C5B 19.6(7) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 120.1(10) . . ? C4B C3B C2 119.6(10) . . ? C4B C3B C14B 120.1(10) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C4B 120.6(14) . . ? C6 C5B C21B 121.0(13) . . ? C4B C5B C21B 117.8(13) . . ? C3B C14B H14A 110.6 . . ? C3B C14B H14B 110.6 . . ? C3B C14B O2B 105.8(8) . . ? H14A C14B H14B 108.7 . . ? O2B C14B H14A 110.6 . . ? O2B C14B H14B 110.6 . . ? C3A C4A C30A 121.4(14) . . ? C3A C4A C5A 117.3(19) . . ? C5A C4A C30A 121.3(16) . . ? C4A C30A H30A 109.6 . . ? C4A C30A H30B 109.6 . . ? H30A C30A H30B 108.1 . . ? C31A C30A C4A 110.4(16) . . ? C31A C30A H30A 109.6 . . ? C31A C30A H30B 109.6 . . ? H30C C30B H30D 107.4 . . ? C31B C30B H30C 108.3 . . ? C31B C30B H30D 108.3 . . ? C31B C30B C4B 115.9(9) . . ? C4B C30B H30C 108.3 . . ? C4B C30B H30D 108.3 . . ? C18 C17 C16 120.0(5) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C3B C4B C5B 119.5(10) . . ? C3B C4B C30B 120.2(8) . . ? C5B C4B C30B 120.3(10) . . ? C23B C24B H24B 119.5 . . ? C25B C24B C23B 121.1(10) . . ? C25B C24B H24B 119.5 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 125(2) . . ? C2 C3A C14A 118.9(19) . . ? C4A C3A C14A 115.4(19) . . ? C6 C5A C21A 119(2) . . ? C6 C5A C4A 119(2) . . ? C4A C5A C21A 122(2) . . ? O2A C14A C3A 105.4(12) . . ? O2A C14A H14C 110.7 . . ? O2A C14A H14D 110.7 . . ? C3A C14A H14C 110.7 . . ? C3A C14A H14D 110.7 . . ? H14C C14A H14D 108.8 . . ? O3B C21B C5B 109.7(9) . . ? O3B C21B H21C 109.7 . . ? O3B C21B H21D 109.7 . . ? C5B C21B H21C 109.7 . . ? C5B C21B H21D 109.7 . . ? H21C C21B H21D 108.2 . . ? C15 O2B C14B 122.7(6) . . ? C22A O3A C21A 115.0(12) . . ? C27A C22A O3A 124.8(12) . . ? C27A C22A C23A 118.4(13) . . ? C23A C22A O3A 116.5(12) . . ? C22A C27A H27A 119.5 . . ? C22A C27A C26A 121.0(13) . . ? C26A C27A H27A 119.5 . . ? C27A C26A H26A 119.9 . . ? C25A C26A C27A 120.1(12) . . ? C25A C26A H26A 119.9 . . ? C26A C25A C24A 121.0(10) . . ? C26A C25A Cl3A 126.2(11) . . ? C24A C25A Cl3A 112.8(11) . . ? C25A C24A H24A 120.8 . . ? C25A C24A C23A 118.4(10) . . ? C23A C24A H24A 120.8 . . ? C22A C23A H23A 119.7 . . ? C24A C23A C22A 120.6(12) . . ? C24A C23A H23A 119.7 . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C18 C17 C16 177.7(4) . . . . ? Cl3B C25B C26B C27B 178.3(10) . . . . ? Cl3B C25B C24B C23B 178.4(11) . . . . ? O2A C15 C20 C19 177.3(8) . . . . ? O2A C15 C16 C17 -178.2(7) . . . . ? O2A C15 O2B C14B 162(3) . . . . ? C9 C8 C13 C12 -1.7(8) . . . . ? C9 C8 O1 C7 0.4(7) . . . . ? C9 C10 C11 Cl1 -178.5(4) . . . . ? C9 C10 C11 C12 1.9(8) . . . . ? O3B C22B C27B C26B -175.9(11) . . . . ? O3B C22B C23B C24B 172.6(11) . . . . ? C8 C9 C10 C11 -2.9(7) . . . . ? C8 O1 C7 C1 175.3(4) . . . . ? C15 O2A C14A C3A -171.2(13) . . . . ? C15 C16 C17 C18 0.9(8) . . . . ? C19 C18 C17 C16 -1.6(8) . . . . ? C18 C19 C20 C15 -0.3(8) . . . . ? C10 C9 C8 C13 2.9(7) . . . . ? C10 C9 C8 O1 -177.4(4) . . . . ? C13 C8 O1 C7 -179.8(4) . . . . ? C13 C12 C11 Cl1 179.7(4) . . . . ? C13 C12 C11 C10 -0.7(8) . . . . ? C20 C15 C16 C17 0.1(8) . . . . ? C20 C15 O2B C14B -13.5(9) . . . . ? C20 C19 C18 Cl2 -178.0(4) . . . . ? C20 C19 C18 C17 1.3(8) . . . . ? C22B O3B C21B C5B -169.1(11) . . . . ? C22B C27B C26B C25B 1.4(17) . . . . ? C22B C23B C24B C25B 5.5(17) . . . . ? C27B C22B C23B C24B -4.1(19) . . . . ? C23B C22B C27B C26B 0.7(19) . . . . ? C11 C12 C13 C8 0.6(8) . . . . ? C16 C15 C20 C19 -0.4(8) . . . . ? C16 C15 O2B C14B 166.0(6) . . . . ? C26B C25B C24B C23B -3.4(16) . . . . ? O1 C8 C13 C12 178.5(5) . . . . ? C2 C1 C7 O1 -84.3(5) . . . . ? C2 C1 C6 C32 -177.9(4) . . . . ? C2 C1 C6 C5B -6.5(9) . . . . ? C2 C1 C6 C5A 15.9(11) . . . . ? C2 C3B C14B O2B 77.1(11) . . . . ? C2 C3B C4B C5B -4.2(16) . . . . ? C2 C3B C4B C30B 173.9(9) . . . . ? C2 C3A C14A O2A 95.5(16) . . . . ? C1 C2 C28 C29 -91.7(5) . . . . ? C1 C2 C3B C14B -179.9(7) . . . . ? C1 C2 C3B C4B -4.5(13) . . . . ? C1 C2 C3A C4A 7(2) . . . . ? C1 C2 C3A C14A 179.1(11) . . . . ? C1 C6 C5B C4B -2.4(13) . . . . ? C1 C6 C5B C21B 168.8(8) . . . . ? C1 C6 C5A C21A 172.5(10) . . . . ? C1 C6 C5A C4A -14.1(17) . . . . ? C28 C2 C1 C7 -3.7(6) . . . . ? C28 C2 C1 C6 -178.9(4) . . . . ? C28 C2 C3B C14B 8.8(12) . . . . ? C28 C2 C3B C4B -175.8(8) . . . . ? C28 C2 C3A C4A 173.8(12) . . . . ? C28 C2 C3A C14A -13.8(18) . . . . ? C21A O3A C22A C27A -6(2) . . . . ? C21A O3A C22A C23A 167.9(13) . . . . ? C7 C1 C6 C32 7.1(7) . . . . ? C7 C1 C6 C5B 178.4(7) . . . . ? C7 C1 C6 C5A -159.2(9) . . . . ? C32 C6 C5B C4B 169.0(8) . . . . ? C32 C6 C5B C21B -19.7(13) . . . . ? C32 C6 C5A C21A 6.0(17) . . . . ? C32 C6 C5A C4A 179.4(10) . . . . ? C6 C1 C7 O1 90.9(5) . . . . ? C6 C5B C4B C3B 7.7(16) . . . . ? C6 C5B C4B C30B -170.4(10) . . . . ? C6 C5B C21B O3B 79.4(12) . . . . ? C33 C32 C6 C1 86.4(6) . . . . ? C33 C32 C6 C5B -84.8(8) . . . . ? C33 C32 C6 C5A -107.3(10) . . . . ? C3B C2 C1 C7 -174.8(7) . . . . ? C3B C2 C1 C6 10.0(8) . . . . ? C3B C2 C28 C29 79.5(8) . . . . ? C3B C2 C3A C4A -97(6) . . . . ? C3B C2 C3A C14A 76(4) . . . . ? C3B C14B O2B C15 -167.6(8) . . . . ? C5B C6 C5A C21A -92(6) . . . . ? C5B C6 C5A C4A 81(6) . . . . ? C14B C3B C4B C5B 171.2(10) . . . . ? C14B C3B C4B C30B -10.7(16) . . . . ? C4A C3A C14A O2A -91.4(15) . . . . ? C30A C4A C3A C2 174.8(14) . . . . ? C30A C4A C3A C14A 2(2) . . . . ? C30A C4A C5A C21A 2(2) . . . . ? C30A C4A C5A C6 -171.4(13) . . . . ? C31B C30B C4B C3B 82.2(12) . . . . ? C31B C30B C4B C5B -99.7(11) . . . . ? C4B C3B C14B O2B -98.3(10) . . . . ? C4B C5B C21B O3B -109.1(11) . . . . ? C24B C25B C26B C27B -0.1(15) . . . . ? C3A C2 C1 C7 163.3(10) . . . . ? C3A C2 C1 C6 -11.9(11) . . . . ? C3A C2 C28 C29 101.7(10) . . . . ? C3A C2 C3B C14B -93(5) . . . . ? C3A C2 C3B C4B 83(5) . . . . ? C3A C4A C30A C31A -101.0(16) . . . . ? C3A C4A C5A C21A -178.0(15) . . . . ? C3A C4A C5A C6 9(2) . . . . ? C5A C21A O3A C22A 171.2(16) . . . . ? C5A C6 C5B C4B -98(6) . . . . ? C5A C6 C5B C21B 73(6) . . . . ? C5A C4A C30A C31A 79.1(17) . . . . ? C5A C4A C3A C2 -5(2) . . . . ? C5A C4A C3A C14A -177.9(14) . . . . ? C14A O2A C15 C20 -6.7(14) . . . . ? C14A O2A C15 C16 171.2(8) . . . . ? C14A O2A C15 O2B -12(2) . . . . ? C21B O3B C22B C27B -17.1(17) . . . . ? C21B O3B C22B C23B 166.1(10) . . . . ? C21B C5B C4B C3B -163.8(10) . . . . ? C21B C5B C4B C30B 18.1(15) . . . . ? O2B C15 C20 C19 179.1(5) . . . . ? O2B C15 C16 C17 -179.3(5) . . . . ? O3A C21A C5A C6 59.6(18) . . . . ? O3A C21A C5A C4A -113.6(16) . . . . ? O3A C22A C27A C26A 176.3(14) . . . . ? O3A C22A C23A C24A -170.6(13) . . . . ? C22A C27A C26A C25A -5(2) . . . . ? C27A C22A C23A C24A 4(2) . . . . ? C27A C26A C25A C24A 1.8(18) . . . . ? C27A C26A C25A Cl3A -176.2(15) . . . . ? C26A C25A C24A C23A 4.2(17) . . . . ? C25A C24A C23A C22A -7(2) . . . . ? C23A C22A C27A C26A 3(2) . . . . ? Cl3A C25A C24A C23A -177.5(13) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.048 0.000 0.500 370 34 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962426' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-ea-262K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-ea, 262 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Cl3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Cl3 O5' _chemical_formula_weight 672.05 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.7104(4) _cell_length_b 13.4378(9) _cell_length_c 14.6582(12) _cell_angle_alpha 111.156(7) _cell_angle_beta 92.048(5) _cell_angle_gamma 89.974(4) _cell_volume 1782.5(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4053 _cell_measurement_temperature 262(2) _cell_measurement_theta_max 29.0811 _cell_measurement_theta_min 4.1363 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 708 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_unetI/netI 0.0693 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 17513 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 4.14 _diffrn_ambient_temperature 262(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.850 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0166698000 _diffrn_orient_matrix_UB_12 0.0100436000 _diffrn_orient_matrix_UB_13 0.0426348000 _diffrn_orient_matrix_UB_21 0.0010932000 _diffrn_orient_matrix_UB_22 -0.0557009000 _diffrn_orient_matrix_UB_23 0.0269032000 _diffrn_orient_matrix_UB_31 0.0711643000 _diffrn_orient_matrix_UB_32 -0.0007206000 _diffrn_orient_matrix_UB_33 -0.0124345000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4655 _reflns_number_total 8157 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.477 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.092 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 8157 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1544 _refine_ls_R_factor_gt 0.1114 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1920P)^2^+1.4541P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3405 _refine_ls_wR_factor_ref 0.3675 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 O2B-C15 \\sim O2A-C15 with sigma of 0.02 3. Others Sof(O2A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)= Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C14A)=Sof(H14C)= Sof(H14D)=Sof(O3A)=Sof(C22A)=Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)= Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(Cl3A)=1-FVAR(1) Sof(Cl3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)= Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C3B)=Sof(C5B)=Sof(C14B)=Sof(H14A)=Sof(H14B)= Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C4B)= Sof(C24B)=Sof(H24B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21A(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C14A(H14C,H14D), C21B(H21C,H21D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.97674(19) 0.11102(14) 0.96213(11) 0.0817(5) Uani 1 1 d . . . Cl1 Cl 1.71571(15) 0.03846(16) 0.12707(12) 0.0846(6) Uani 1 1 d . . . Cl3B Cl 0.5319(15) 0.9362(10) 0.3206(14) 0.125(5) Uani 0.581(15) 1 d A 1 . O2A O 0.9514(15) 0.2818(10) 0.6504(8) 0.061(4) Uiso 0.419(15) 1 d A 2 . C9 C 1.3179(5) 0.1037(4) 0.1752(3) 0.0490(10) Uani 1 1 d . . . H9 H 1.2335 0.0793 0.1428 0.059 Uiso 1 1 calc . . R O3B O 0.6973(10) 0.5363(7) 0.3613(6) 0.050(2) Uiso 0.581(15) 1 d A 1 . C8 C 1.3238(4) 0.1869(4) 0.2655(3) 0.0444(9) Uani 1 1 d . . . C15 C 0.9312(5) 0.2437(4) 0.7205(3) 0.0510(11) Uani 1 1 d . . . C19 C 0.8375(5) 0.1465(4) 0.8145(4) 0.0610(13) Uani 1 1 d . . . H19 H 0.7650 0.1091 0.8275 0.073 Uiso 1 1 calc A . R C18 C 0.9595(6) 0.1647(4) 0.8703(4) 0.0563(12) Uani 1 1 d A . . C10 C 1.4400(5) 0.0575(4) 0.1341(4) 0.0550(11) Uani 1 1 d . . . H10 H 1.4377 0.0006 0.0745 0.066 Uiso 1 1 calc . . R C12 C 1.5700(5) 0.1794(5) 0.2698(4) 0.0579(12) Uani 1 1 d . . . H12 H 1.6549 0.2048 0.3010 0.069 Uiso 1 1 calc . . R C13 C 1.4500(5) 0.2247(4) 0.3112(4) 0.0586(12) Uani 1 1 d . . . H13 H 1.4536 0.2817 0.3708 0.070 Uiso 1 1 calc . . R C20 C 0.8255(5) 0.1856(4) 0.7381(4) 0.0583(12) Uani 1 1 d A . . H20 H 0.7452 0.1722 0.6988 0.070 Uiso 1 1 calc . . R C22B C 0.6685(13) 0.6286(10) 0.3503(8) 0.050(4) Uiso 0.581(15) 1 d A 1 . C27B C 0.7060(12) 0.7264(7) 0.4233(9) 0.051(3) Uiso 0.581(15) 1 d A 1 . H27B H 0.7609 0.7295 0.4776 0.061 Uiso 0.581(15) 1 calc A 1 R C23B C 0.5984(12) 0.6227(10) 0.2668(9) 0.058(3) Uiso 0.581(15) 1 d A 1 . H23B H 0.5813 0.5568 0.2174 0.069 Uiso 0.581(15) 1 calc A 1 R C11 C 1.5630(5) 0.0958(5) 0.1815(4) 0.0557(12) Uani 1 1 d . . . C16 C 1.0527(6) 0.2617(4) 0.7775(4) 0.0626(13) Uani 1 1 d A . . H16 H 1.1253 0.2993 0.7649 0.075 Uiso 1 1 calc . . R C25B C 0.5835(9) 0.8112(8) 0.3264(8) 0.049(2) Uiso 0.581(15) 1 d A 1 . C26B C 0.6580(10) 0.8184(8) 0.4114(8) 0.053(3) Uiso 0.581(15) 1 d A 1 . H26B H 0.6755 0.8847 0.4601 0.063 Uiso 0.581(15) 1 calc A 1 R O1 O 1.2100(3) 0.2364(3) 0.3146(2) 0.0531(8) Uani 1 1 d A . . C2 C 0.9423(4) 0.2269(3) 0.4208(3) 0.0432(9) Uani 1 1 d . . . C1 C 0.9762(4) 0.2639(3) 0.3464(3) 0.0447(9) Uani 1 1 d A . . C28 C 0.9979(5) 0.1208(4) 0.4226(4) 0.0503(11) Uani 1 1 d A . . H28A H 1.0865 0.1074 0.3921 0.060 Uiso 1 1 calc . . R H28B H 1.0120 0.1261 0.4900 0.060 Uiso 1 1 calc . . R C21A C 0.8361(17) 0.5452(11) 0.4354(10) 0.050(3) Uiso 0.419(15) 1 d A 2 . H21A H 0.8023 0.5840 0.4999 0.060 Uiso 0.419(15) 1 calc A 2 R H21B H 0.9177 0.5820 0.4268 0.060 Uiso 0.419(15) 1 calc A 2 R C7 C 1.0751(4) 0.2017(4) 0.2715(3) 0.0471(10) Uani 1 1 d . . . H7A H 1.0627 0.1257 0.2566 0.057 Uiso 1 1 calc A . R H7B H 1.0614 0.2160 0.2116 0.057 Uiso 1 1 calc . . R C32 C 0.9578(5) 0.4011(4) 0.2642(4) 0.0561(12) Uani 1 1 d A . . H32A H 1.0495 0.3785 0.2418 0.067 Uiso 1 1 calc . . R H32B H 0.9563 0.4784 0.2877 0.067 Uiso 1 1 calc . . R C6 C 0.9262(5) 0.3636(3) 0.3469(3) 0.0440(9) Uani 1 1 d . . . C33 C 0.8516(7) 0.3552(6) 0.1778(4) 0.0787(17) Uani 1 1 d . . . H33A H 0.8751 0.3785 0.1256 0.118 Uiso 1 1 calc A . GR H33B H 0.7613 0.3799 0.1993 0.118 Uiso 1 1 calc . . GR H33C H 0.8525 0.2786 0.1549 0.118 Uiso 1 1 calc . . GR C3B C 0.8373(12) 0.2830(11) 0.4859(10) 0.032(2) Uani 0.581(15) 1 d A 1 . C29 C 0.9016(6) 0.0285(4) 0.3701(4) 0.0646(14) Uani 1 1 d . . . H29A H 0.8943 0.0186 0.3018 0.097 Uiso 1 1 calc A . GR H29B H 0.8123 0.0432 0.3976 0.097 Uiso 1 1 calc . . GR H29C H 0.9369 -0.0351 0.3773 0.097 Uiso 1 1 calc . . GR C5B C 0.8279(15) 0.4200(16) 0.4195(16) 0.038(3) Uani 0.581(15) 1 d A 1 . C14B C 0.8060(10) 0.2435(7) 0.5681(6) 0.037(2) Uiso 0.581(15) 1 d A 1 . H14A H 0.7177 0.2702 0.5950 0.045 Uiso 0.581(15) 1 calc A 1 R H14B H 0.8019 0.1662 0.5433 0.045 Uiso 0.581(15) 1 calc A 1 R C4A C 0.8402(16) 0.3982(11) 0.5084(10) 0.044(3) Uani 0.419(15) 1 d A 2 . C30A C 0.7625(13) 0.4712(10) 0.5978(10) 0.055(4) Uani 0.419(15) 1 d A 2 . H30A H 0.7794 0.4484 0.6528 0.066 Uiso 0.419(15) 1 calc A 2 R H30B H 0.7957 0.5442 0.6163 0.066 Uiso 0.419(15) 1 calc A 2 R C30B C 0.6610(11) 0.4257(8) 0.5487(7) 0.049(2) Uani 0.581(15) 1 d A 1 . H30C H 0.6009 0.3692 0.5514 0.059 Uiso 0.581(15) 1 calc A 1 R H30D H 0.6086 0.4665 0.5172 0.059 Uiso 0.581(15) 1 calc A 1 R C31B C 0.6989(11) 0.4995(8) 0.6543(8) 0.065(3) Uani 0.581(15) 1 d A 1 . H31A H 0.7407 0.5640 0.6537 0.097 Uiso 0.581(15) 1 calc A 1 GR H31B H 0.7625 0.4640 0.6836 0.097 Uiso 0.581(15) 1 calc A 1 GR H31C H 0.6171 0.5165 0.6915 0.097 Uiso 0.581(15) 1 calc A 1 GR C17 C 1.0651(6) 0.2229(5) 0.8541(4) 0.0664(14) Uani 1 1 d . . . H17 H 1.1450 0.2367 0.8938 0.080 Uiso 1 1 calc A . R C4B C 0.7783(12) 0.3753(7) 0.4857(7) 0.041(2) Uani 0.581(15) 1 d A 1 . C24B C 0.5529(11) 0.7140(9) 0.2555(9) 0.062(3) Uiso 0.581(15) 1 d A 1 . H24B H 0.5011 0.7100 0.1997 0.074 Uiso 0.581(15) 1 calc A 1 R C31A C 0.6128(19) 0.466(2) 0.573(2) 0.093(7) Uani 0.419(15) 1 d A 2 . H31D H 0.5983 0.4683 0.5087 0.140 Uiso 0.419(15) 1 calc A 2 GR H31E H 0.5682 0.5252 0.6198 0.140 Uiso 0.419(15) 1 calc A 2 GR H31F H 0.5749 0.4004 0.5743 0.140 Uiso 0.419(15) 1 calc A 2 GR C3A C 0.8814(19) 0.2922(19) 0.5044(16) 0.043(4) Uani 0.419(15) 1 d A 2 . C5A C 0.872(2) 0.432(3) 0.426(3) 0.047(5) Uani 0.419(15) 1 d A 2 . C14A C 0.843(2) 0.2590(14) 0.5865(13) 0.060(4) Uiso 0.419(15) 1 d A 2 . H14C H 0.7628 0.2973 0.6176 0.072 Uiso 0.419(15) 1 calc A 2 R H14D H 0.8224 0.1831 0.5626 0.072 Uiso 0.419(15) 1 calc A 2 R C21B C 0.7918(12) 0.5327(8) 0.4333(7) 0.046(2) Uiso 0.581(15) 1 d A 1 . H21C H 0.7533 0.5667 0.4971 0.056 Uiso 0.581(15) 1 calc A 1 R H21D H 0.8747 0.5718 0.4310 0.056 Uiso 0.581(15) 1 calc A 1 R O2B O 0.9152(10) 0.2820(6) 0.6440(5) 0.049(2) Uiso 0.581(15) 1 d A 1 . O3A O 0.7290(15) 0.5411(11) 0.3597(10) 0.060(4) Uiso 0.419(15) 1 d A 2 . C22A C 0.6736(15) 0.6416(12) 0.3688(10) 0.040(4) Uiso 0.419(15) 1 d A 2 . C27A C 0.6924(14) 0.7371(8) 0.4458(11) 0.040(4) Uiso 0.419(15) 1 d A 2 . H27A H 0.7392 0.7369 0.5022 0.049 Uiso 0.419(15) 1 calc A 2 R C26A C 0.6457(11) 0.8325(9) 0.4436(10) 0.043(3) Uiso 0.419(15) 1 d A 2 . H26A H 0.6625 0.8955 0.4968 0.052 Uiso 0.419(15) 1 calc A 2 R C25A C 0.5741(10) 0.8334(8) 0.3618(9) 0.036(3) Uiso 0.419(15) 1 d A 2 . C24A C 0.5489(12) 0.7420(9) 0.2828(9) 0.040(3) Uiso 0.419(15) 1 d A 2 . H24A H 0.5035 0.7440 0.2265 0.048 Uiso 0.419(15) 1 calc A 2 R C23A C 0.5935(14) 0.6451(11) 0.2886(11) 0.045(4) Uiso 0.419(15) 1 d A 2 . H23A H 0.5692 0.5816 0.2380 0.054 Uiso 0.419(15) 1 calc A 2 R Cl3A Cl 0.510(2) 0.9454(11) 0.3463(17) 0.097(4) Uani 0.419(15) 1 d A 2 . 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 Cl2 0.1057(12) 0.0882(11) 0.0647(8) 0.0433(8) 0.0076(8) 0.0102(9) Cl1 0.0530(8) 0.1157(14) 0.0808(10) 0.0290(9) 0.0177(7) 0.0232(8) Cl3B 0.065(4) 0.119(7) 0.255(14) 0.151(9) -0.041(6) -0.014(4) C9 0.043(2) 0.051(3) 0.051(2) 0.016(2) 0.0022(18) -0.0044(19) C8 0.044(2) 0.043(2) 0.045(2) 0.0148(18) 0.0012(17) -0.0038(17) C15 0.064(3) 0.038(2) 0.056(3) 0.022(2) 0.019(2) 0.007(2) C19 0.056(3) 0.065(3) 0.077(3) 0.043(3) 0.012(2) 0.007(2) C18 0.068(3) 0.052(3) 0.054(3) 0.022(2) 0.017(2) 0.013(2) C10 0.056(3) 0.061(3) 0.048(2) 0.018(2) 0.011(2) 0.005(2) C12 0.044(2) 0.069(3) 0.062(3) 0.026(3) -0.004(2) -0.004(2) C13 0.051(3) 0.058(3) 0.054(3) 0.006(2) -0.004(2) -0.005(2) C20 0.053(3) 0.066(3) 0.071(3) 0.043(3) 0.009(2) 0.006(2) C11 0.043(2) 0.071(3) 0.058(3) 0.029(2) 0.009(2) 0.010(2) C16 0.073(3) 0.048(3) 0.065(3) 0.017(2) 0.012(3) -0.014(2) O1 0.0397(15) 0.0511(19) 0.0552(18) 0.0028(14) 0.0048(13) -0.0015(13) C2 0.048(2) 0.033(2) 0.051(2) 0.0177(17) 0.0033(18) 0.0023(17) C1 0.043(2) 0.041(2) 0.049(2) 0.0152(18) 0.0008(18) -0.0007(17) C28 0.051(2) 0.043(2) 0.060(3) 0.022(2) 0.002(2) 0.0142(19) C7 0.040(2) 0.047(2) 0.051(2) 0.0144(19) 0.0012(18) -0.0018(18) C32 0.055(3) 0.060(3) 0.063(3) 0.033(2) 0.005(2) -0.003(2) C6 0.050(2) 0.039(2) 0.046(2) 0.0181(18) 0.0020(18) -0.0002(18) C33 0.088(4) 0.097(5) 0.053(3) 0.031(3) -0.005(3) 0.005(3) C3B 0.029(6) 0.036(4) 0.036(6) 0.020(4) -0.002(4) 0.008(5) C29 0.073(3) 0.036(2) 0.080(3) 0.015(2) 0.005(3) 0.001(2) C5B 0.035(8) 0.034(6) 0.054(7) 0.026(5) 0.011(7) 0.005(6) C4A 0.036(7) 0.042(6) 0.054(7) 0.017(5) 0.005(5) -0.009(5) C30A 0.060(8) 0.049(7) 0.060(8) 0.026(6) 0.011(6) 0.001(6) C30B 0.044(6) 0.044(5) 0.057(5) 0.015(4) 0.003(4) 0.008(4) C31B 0.065(6) 0.054(5) 0.068(6) 0.011(5) 0.020(5) 0.004(4) C17 0.073(3) 0.059(3) 0.060(3) 0.013(2) -0.005(3) -0.006(3) C4B 0.040(5) 0.033(4) 0.048(4) 0.013(3) 0.003(4) -0.003(4) C31A 0.050(10) 0.101(17) 0.140(19) 0.054(15) 0.030(10) 0.005(9) C3A 0.035(9) 0.054(8) 0.043(8) 0.025(7) -0.012(6) 0.011(8) C5A 0.038(12) 0.048(9) 0.064(9) 0.030(7) -0.007(11) -0.003(10) Cl3A 0.068(6) 0.062(4) 0.183(8) 0.072(5) -0.024(5) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl2 C18 1.744(5) . ? Cl1 C11 1.752(5) . ? Cl3B C25B 1.783(14) . ? O2A C15 1.322(10) . ? O2A C14A 1.34(2) . ? C9 H9 0.9300 . ? C9 C8 1.389(6) . ? C9 C10 1.391(7) . ? O3B C22B 1.335(15) . ? O3B C21B 1.388(13) . ? C8 C13 1.380(6) . ? C8 O1 1.376(5) . ? C15 C20 1.377(7) . ? C15 C16 1.390(8) . ? C15 O2B 1.397(8) . ? C19 H19 0.9300 . ? C19 C18 1.385(8) . ? C19 C20 1.399(7) . ? C18 C17 1.370(8) . ? C10 H10 0.9300 . ? C10 C11 1.362(7) . ? C12 H12 0.9300 . ? C12 C13 1.372(7) . ? C12 C11 1.374(7) . ? C13 H13 0.9300 . ? C20 H20 0.9300 . ? C22B C27B 1.400(11) . ? C22B C23B 1.357(11) . ? C27B H27B 0.9300 . ? C27B C26B 1.388(10) . ? C23B H23B 0.9300 . ? C23B C24B 1.366(11) . ? C16 H16 0.9300 . ? C16 C17 1.398(8) . ? C25B C26B 1.391(10) . ? C25B C24B 1.369(11) . ? C26B H26B 0.9300 . ? O1 C7 1.436(5) . ? C2 C1 1.401(6) . ? C2 C28 1.534(6) . ? C2 C3B 1.438(14) . ? C2 C3A 1.38(2) . ? C1 C7 1.496(6) . ? C1 C6 1.422(6) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C29 1.505(7) . ? C21A H21A 0.9700 . ? C21A H21B 0.9700 . ? C21A C5A 1.52(4) . ? C21A O3A 1.480(19) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C6 1.512(6) . ? C32 C33 1.546(8) . ? C6 C5B 1.45(2) . ? C6 C5A 1.32(4) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C3B C14B 1.521(16) . ? C3B C4B 1.367(15) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C5B C4B 1.41(2) . ? C5B C21B 1.50(2) . ? C14B H14A 0.9700 . ? C14B H14B 0.9700 . ? C14B O2B 1.459(11) . ? C4A C30A 1.546(19) . ? C4A C3A 1.46(3) . ? C4A C5A 1.47(4) . ? C30A H30A 0.9700 . ? C30A H30B 0.9700 . ? C30A C31A 1.48(2) . ? C30B H30C 0.9700 . ? C30B H30D 0.9700 . ? C30B C31B 1.538(14) . ? C30B C4B 1.494(15) . ? C31B H31A 0.9600 . ? C31B H31B 0.9600 . ? C31B H31C 0.9600 . ? C17 H17 0.9300 . ? C24B H24B 0.9300 . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? C3A C14A 1.48(3) . ? C14A H14C 0.9700 . ? C14A H14D 0.9700 . ? C21B H21C 0.9700 . ? C21B H21D 0.9700 . ? O3A C22A 1.42(2) . ? C22A C27A 1.376(13) . ? C22A C23A 1.402(12) . ? C27A H27A 0.9300 . ? C27A C26A 1.371(11) . ? C26A H26A 0.9300 . ? C26A C25A 1.369(11) . ? C25A C24A 1.365(12) . ? C25A Cl3A 1.715(18) . ? C24A H24A 0.9300 . ? C24A C23A 1.403(12) . ? C23A H23A 0.9300 . ? 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 C15 O2A C14A 110.8(11) . . ? C8 C9 H9 120.5 . . ? C8 C9 C10 119.0(4) . . ? C10 C9 H9 120.5 . . ? C22B O3B C21B 120.7(9) . . ? C13 C8 C9 119.8(4) . . ? O1 C8 C9 124.2(4) . . ? O1 C8 C13 115.9(4) . . ? O2A C15 C20 133.0(8) . . ? O2A C15 C16 106.8(7) . . ? O2A C15 O2B 14.9(6) . . ? C20 C15 C16 119.8(5) . . ? C20 C15 O2B 119.1(6) . . ? C16 C15 O2B 121.1(6) . . ? C18 C19 H19 120.6 . . ? C18 C19 C20 118.8(5) . . ? C20 C19 H19 120.6 . . ? C19 C18 Cl2 118.6(4) . . ? C17 C18 Cl2 120.3(4) . . ? C17 C18 C19 121.1(5) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.8(5) . . ? C11 C10 H10 120.1 . . ? C13 C12 H12 120.5 . . ? C13 C12 C11 118.9(4) . . ? C11 C12 H12 120.5 . . ? C8 C13 H13 119.6 . . ? C12 C13 C8 120.8(4) . . ? C12 C13 H13 119.6 . . ? C15 C20 C19 120.7(5) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? O3B C22B C27B 121.1(9) . . ? O3B C22B C23B 116.7(10) . . ? C23B C22B C27B 122.1(11) . . ? C22B C27B H27B 121.3 . . ? C26B C27B C22B 117.4(9) . . ? C26B C27B H27B 121.3 . . ? C22B C23B H23B 120.1 . . ? C22B C23B C24B 119.7(12) . . ? C24B C23B H23B 120.1 . . ? C10 C11 Cl1 119.1(4) . . ? C10 C11 C12 121.6(4) . . ? C12 C11 Cl1 119.3(4) . . ? C15 C16 H16 120.1 . . ? C15 C16 C17 119.7(5) . . ? C17 C16 H16 120.1 . . ? C26B C25B Cl3B 114.6(9) . . ? C24B C25B Cl3B 124.7(8) . . ? C24B C25B C26B 120.7(8) . . ? C27B C26B C25B 119.8(9) . . ? C27B C26B H26B 120.1 . . ? C25B C26B H26B 120.1 . . ? C8 O1 C7 119.2(3) . . ? C1 C2 C28 121.0(4) . . ? C1 C2 C3B 117.4(6) . . ? C3B C2 C28 120.9(6) . . ? C3A C2 C1 121.5(10) . . ? C3A C2 C28 116.4(10) . . ? C3A C2 C3B 19.9(6) . . ? C2 C1 C7 119.0(4) . . ? C2 C1 C6 120.3(4) . . ? C6 C1 C7 120.6(4) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? H28A C28 H28B 107.9 . . ? C29 C28 C2 112.3(4) . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? H21A C21A H21B 108.3 . . ? C5A C21A H21A 109.9 . . ? C5A C21A H21B 109.9 . . ? O3A C21A H21A 109.9 . . ? O3A C21A H21B 109.9 . . ? O3A C21A C5A 109.1(15) . . ? O1 C7 C1 105.6(3) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? H7A C7 H7B 108.7 . . ? H32A C32 H32B 108.0 . . ? C6 C32 H32A 109.4 . . ? C6 C32 H32B 109.4 . . ? C6 C32 C33 111.0(4) . . ? C33 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C1 C6 C32 120.1(4) . . ? C1 C6 C5B 118.6(9) . . ? C5B C6 C32 120.6(9) . . ? C5A C6 C1 120.2(15) . . ? C5A C6 C32 118.7(15) . . ? C5A C6 C5B 18.0(11) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 116.3(9) . . ? C4B C3B C2 124.3(11) . . ? C4B C3B C14B 118.8(11) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 119.8(14) . . ? C4B C5B C6 121.0(15) . . ? C4B C5B C21B 118.8(15) . . ? C3B C14B H14A 110.0 . . ? C3B C14B H14B 110.0 . . ? H14A C14B H14B 108.4 . . ? O2B C14B C3B 108.4(7) . . ? O2B C14B H14A 110.0 . . ? O2B C14B H14B 110.0 . . ? C3A C4A C30A 119.2(13) . . ? C3A C4A C5A 118.9(19) . . ? C5A C4A C30A 121.9(17) . . ? C4A C30A H30A 109.7 . . ? C4A C30A H30B 109.7 . . ? H30A C30A H30B 108.2 . . ? C31A C30A C4A 109.7(16) . . ? C31A C30A H30A 109.7 . . ? C31A C30A H30B 109.7 . . ? H30C C30B H30D 107.3 . . ? C31B C30B H30C 108.2 . . ? C31B C30B H30D 108.2 . . ? C4B C30B H30C 108.2 . . ? C4B C30B H30D 108.2 . . ? C4B C30B C31B 116.4(10) . . ? C18 C17 C16 119.8(5) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C3B C4B C5B 117.4(12) . . ? C3B C4B C30B 122.4(9) . . ? C5B C4B C30B 120.1(11) . . ? C23B C24B C25B 120.0(10) . . ? C23B C24B H24B 120.0 . . ? C25B C24B H24B 120.0 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 117.4(17) . . ? C2 C3A C14A 124.6(18) . . ? C4A C3A C14A 117.7(18) . . ? C6 C5A C21A 122(2) . . ? C6 C5A C4A 120(3) . . ? C4A C5A C21A 118(3) . . ? O2A C14A C3A 107.2(13) . . ? O2A C14A H14C 110.3 . . ? O2A C14A H14D 110.3 . . ? C3A C14A H14C 110.3 . . ? C3A C14A H14D 110.3 . . ? H14C C14A H14D 108.5 . . ? O3B C21B C5B 111.2(10) . . ? O3B C21B H21C 109.4 . . ? O3B C21B H21D 109.4 . . ? C5B C21B H21C 109.4 . . ? C5B C21B H21D 109.4 . . ? H21C C21B H21D 108.0 . . ? C15 O2B C14B 122.5(7) . . ? C22A O3A C21A 114.3(11) . . ? C27A C22A O3A 127.9(11) . . ? C27A C22A C23A 115.9(12) . . ? C23A C22A O3A 116.2(11) . . ? C22A C27A H27A 118.3 . . ? C26A C27A C22A 123.4(12) . . ? C26A C27A H27A 118.3 . . ? C27A C26A H26A 120.6 . . ? C25A C26A C27A 118.8(11) . . ? C25A C26A H26A 120.6 . . ? C26A C25A Cl3A 124.9(10) . . ? C24A C25A C26A 121.6(10) . . ? C24A C25A Cl3A 113.5(10) . . ? C25A C24A H24A 120.9 . . ? C25A C24A C23A 118.3(10) . . ? C23A C24A H24A 120.9 . . ? C22A C23A C24A 121.7(12) . . ? C22A C23A H23A 119.2 . . ? C24A C23A H23A 119.2 . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C18 C17 C16 177.2(4) . . . . ? Cl3B C25B C26B C27B -178.8(10) . . . . ? Cl3B C25B C24B C23B 179.5(11) . . . . ? O2A C15 C20 C19 173.7(9) . . . . ? O2A C15 C16 C17 -175.7(7) . . . . ? O2A C15 O2B C14B 146(3) . . . . ? C9 C8 C13 C12 -1.7(8) . . . . ? C9 C8 O1 C7 -0.1(7) . . . . ? C9 C10 C11 Cl1 -178.5(4) . . . . ? C9 C10 C11 C12 0.3(8) . . . . ? O3B C22B C27B C26B -172.5(11) . . . . ? O3B C22B C23B C24B 173.1(11) . . . . ? C8 C9 C10 C11 -1.5(7) . . . . ? C8 O1 C7 C1 175.1(4) . . . . ? C15 O2A C14A C3A -173.0(13) . . . . ? C15 C16 C17 C18 2.1(8) . . . . ? C19 C18 C17 C16 -2.5(8) . . . . ? C18 C19 C20 C15 -1.9(8) . . . . ? C10 C9 C8 C13 2.2(7) . . . . ? C10 C9 C8 O1 -177.9(4) . . . . ? C13 C8 O1 C7 179.8(4) . . . . ? C13 C12 C11 Cl1 179.1(4) . . . . ? C13 C12 C11 C10 0.3(8) . . . . ? C20 C15 C16 C17 -1.6(8) . . . . ? C20 C15 O2B C14B -14.5(10) . . . . ? C20 C19 C18 Cl2 -177.3(4) . . . . ? C20 C19 C18 C17 2.4(8) . . . . ? C22B O3B C21B C5B -168.9(12) . . . . ? C22B C27B C26B C25B -4.1(16) . . . . ? C22B C23B C24B C25B 3.0(18) . . . . ? C27B C22B C23B C24B -5(2) . . . . ? C23B C22B C27B C26B 5.7(19) . . . . ? C11 C12 C13 C8 0.4(8) . . . . ? C16 C15 C20 C19 1.5(8) . . . . ? C16 C15 O2B C14B 164.4(6) . . . . ? C26B C25B C24B C23B -1.6(16) . . . . ? O1 C8 C13 C12 178.4(5) . . . . ? C2 C1 C7 O1 -84.2(5) . . . . ? C2 C1 C6 C32 -177.3(4) . . . . ? C2 C1 C6 C5B -6.6(10) . . . . ? C2 C1 C6 C5A 14.0(12) . . . . ? C2 C3B C14B O2B 77.1(10) . . . . ? C2 C3B C4B C5B -2.4(16) . . . . ? C2 C3B C4B C30B 174.5(10) . . . . ? C2 C3A C14A O2A 91.2(17) . . . . ? C1 C2 C28 C29 -91.8(5) . . . . ? C1 C2 C3B C14B -177.9(7) . . . . ? C1 C2 C3B C4B -6.5(13) . . . . ? C1 C2 C3A C4A 6.3(16) . . . . ? C1 C2 C3A C14A -179.6(12) . . . . ? C1 C6 C5B C4B -2.6(17) . . . . ? C1 C6 C5B C21B 169.6(9) . . . . ? C1 C6 C5A C21A 171.1(12) . . . . ? C1 C6 C5A C4A -11(2) . . . . ? C28 C2 C1 C7 -3.8(6) . . . . ? C28 C2 C1 C6 -178.6(4) . . . . ? C28 C2 C3B C14B 11.6(11) . . . . ? C28 C2 C3B C4B -177.0(8) . . . . ? C28 C2 C3A C4A 173.9(9) . . . . ? C28 C2 C3A C14A -12.0(18) . . . . ? C21A O3A C22A C27A -10(2) . . . . ? C21A O3A C22A C23A 167.4(13) . . . . ? C7 C1 C6 C32 7.9(6) . . . . ? C7 C1 C6 C5B 178.6(8) . . . . ? C7 C1 C6 C5A -160.8(11) . . . . ? C32 C6 C5B C4B 168.0(10) . . . . ? C32 C6 C5B C21B -19.8(16) . . . . ? C32 C6 C5A C21A 2(2) . . . . ? C32 C6 C5A C4A -179.9(11) . . . . ? C6 C1 C7 O1 90.7(5) . . . . ? C6 C5B C4B C3B 6.9(19) . . . . ? C6 C5B C4B C30B -170.1(11) . . . . ? C6 C5B C21B O3B 79.3(14) . . . . ? C33 C32 C6 C1 85.5(6) . . . . ? C33 C32 C6 C5B -85.0(9) . . . . ? C33 C32 C6 C5A -105.6(11) . . . . ? C3B C2 C1 C7 -174.2(6) . . . . ? C3B C2 C1 C6 10.9(8) . . . . ? C3B C2 C28 C29 78.4(8) . . . . ? C3B C2 C3A C4A -78(4) . . . . ? C3B C2 C3A C14A 96(5) . . . . ? C3B C14B O2B C15 -167.7(8) . . . . ? C5B C6 C5A C21A -99(7) . . . . ? C5B C6 C5A C4A 79(7) . . . . ? C14B C3B C4B C5B 168.8(11) . . . . ? C14B C3B C4B C30B -14.3(15) . . . . ? C4A C3A C14A O2A -94.7(15) . . . . ? C30A C4A C3A C2 175.8(13) . . . . ? C30A C4A C3A C14A 1(2) . . . . ? C30A C4A C5A C21A 5(2) . . . . ? C30A C4A C5A C6 -173.2(15) . . . . ? C31B C30B C4B C3B 84.7(12) . . . . ? C31B C30B C4B C5B -98.4(13) . . . . ? C4B C3B C14B O2B -94.8(10) . . . . ? C4B C5B C21B O3B -108.3(14) . . . . ? C24B C25B C26B C27B 2.2(15) . . . . ? C3A C2 C1 C7 163.3(9) . . . . ? C3A C2 C1 C6 -11.6(10) . . . . ? C3A C2 C28 C29 100.5(10) . . . . ? C3A C2 C3B C14B -71(4) . . . . ? C3A C2 C3B C4B 101(5) . . . . ? C3A C4A C30A C31A -99.3(16) . . . . ? C3A C4A C5A C21A -176.2(14) . . . . ? C3A C4A C5A C6 6(2) . . . . ? C5A C21A O3A C22A 171.9(16) . . . . ? C5A C6 C5B C4B -103(8) . . . . ? C5A C6 C5B C21B 69(7) . . . . ? C5A C4A C30A C31A 79.7(19) . . . . ? C5A C4A C3A C2 -3(2) . . . . ? C5A C4A C3A C14A -177.8(15) . . . . ? C14A O2A C15 C20 1.4(16) . . . . ? C14A O2A C15 C16 174.4(10) . . . . ? C14A O2A C15 O2B -22(2) . . . . ? C21B O3B C22B C27B -15.1(17) . . . . ? C21B O3B C22B C23B 166.6(11) . . . . ? C21B C5B C4B C3B -165.3(11) . . . . ? C21B C5B C4B C30B 17.7(18) . . . . ? O2B C15 C20 C19 -179.6(6) . . . . ? O2B C15 C16 C17 179.5(6) . . . . ? O3A C21A C5A C6 62.5(19) . . . . ? O3A C21A C5A C4A -115.4(17) . . . . ? O3A C22A C27A C26A 173.0(15) . . . . ? O3A C22A C23A C24A -170.9(13) . . . . ? C22A C27A C26A C25A 1(2) . . . . ? C27A C22A C23A C24A 7(2) . . . . ? C27A C26A C25A C24A -0.4(18) . . . . ? C27A C26A C25A Cl3A -179.4(13) . . . . ? C26A C25A C24A C23A 2.7(17) . . . . ? C25A C24A C23A C22A -6(2) . . . . ? C23A C22A C27A C26A -5(2) . . . . ? Cl3A C25A C24A C23A -178.2(13) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.050 0.000 0.500 374 30 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962427' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-ea-298K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-ea, 298 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Cl3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Cl3 O5' _chemical_formula_weight 672.05 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.7599(7) _cell_length_b 13.4660(12) _cell_length_c 14.7073(15) _cell_angle_alpha 110.972(9) _cell_angle_beta 92.061(7) _cell_angle_gamma 89.844(7) _cell_volume 1803.6(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3466 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.1677 _cell_measurement_theta_min 3.8293 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.85621 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 708 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_unetI/netI 0.0700 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 16904 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.23 _diffrn_reflns_theta_min 3.84 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.837 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0161283000 _diffrn_orient_matrix_UB_12 0.0099154000 _diffrn_orient_matrix_UB_13 0.0426434000 _diffrn_orient_matrix_UB_21 0.0014164000 _diffrn_orient_matrix_UB_22 -0.0555329000 _diffrn_orient_matrix_UB_23 0.0265273000 _diffrn_orient_matrix_UB_31 0.0709009000 _diffrn_orient_matrix_UB_32 -0.0005163000 _diffrn_orient_matrix_UB_33 -0.0122172000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4112 _reflns_number_total 8212 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.408 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.071 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 8212 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1470 _refine_ls_R_factor_gt 0.0899 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1645P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2636 _refine_ls_wR_factor_ref 0.3056 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C23B-C22B \\sim C24B-C23B \\sim C25B-C24B \\sim C26B-C25B \\sim C27B-C26B \\sim C27B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 O2B-C15 \\sim O2A-C15 with sigma of 0.02 3. Others Sof(O2A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)= Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C14A)=Sof(H14C)= Sof(H14D)=Sof(O3A)=Sof(C22A)=Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)= Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(Cl3A)=1-FVAR(1) Sof(Cl3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)= Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C3B)=Sof(C5B)=Sof(C14B)=Sof(H14A)=Sof(H14B)= Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C4B)= Sof(C24B)=Sof(H24B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21A(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C14A(H14C,H14D), C21B(H21C,H21D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.97578(15) 0.11079(12) 0.96080(9) 0.0981(5) Uani 1 1 d . . . Cl1 Cl 1.71379(12) 0.03950(13) 0.12823(10) 0.1006(5) Uani 1 1 d . . . Cl3B Cl 0.5306(13) 0.9304(9) 0.3159(11) 0.128(4) Uani 0.566(12) 1 d A 1 . O2A O 0.9513(11) 0.2803(8) 0.6500(6) 0.071(3) Uiso 0.434(12) 1 d A 2 . C9 C 1.3177(4) 0.1054(3) 0.1762(3) 0.0590(9) Uani 1 1 d . . . H9 H 1.2341 0.0813 0.1435 0.071 Uiso 1 1 calc . . R O3B O 0.6987(8) 0.5380(5) 0.3668(5) 0.061(2) Uiso 0.566(12) 1 d A 1 . C8 C 1.3225(3) 0.1868(3) 0.2650(2) 0.0505(8) Uani 1 1 d . . . C15 C 0.9303(4) 0.2424(3) 0.7192(3) 0.0580(9) Uani 1 1 d . . . C19 C 0.8383(4) 0.1466(4) 0.8129(3) 0.0749(11) Uani 1 1 d . . . H19 H 0.7668 0.1082 0.8252 0.090 Uiso 1 1 calc A . R C18 C 0.9577(4) 0.1654(3) 0.8692(3) 0.0651(10) Uani 1 1 d A . . C10 C 1.4401(4) 0.0591(3) 0.1354(3) 0.0643(9) Uani 1 1 d . . . H10 H 1.4378 0.0022 0.0763 0.077 Uiso 1 1 calc . . R C12 C 1.5685(4) 0.1802(4) 0.2698(3) 0.0702(10) Uani 1 1 d . . . H12 H 1.6527 0.2066 0.3005 0.084 Uiso 1 1 calc . . R C13 C 1.4482(4) 0.2241(3) 0.3119(3) 0.0688(10) Uani 1 1 d . . . H13 H 1.4513 0.2790 0.3723 0.083 Uiso 1 1 calc . . R C20 C 0.8256(4) 0.1856(3) 0.7373(3) 0.0658(10) Uani 1 1 d A . . H20 H 0.7452 0.1729 0.6987 0.079 Uiso 1 1 calc . . R C22B C 0.6696(10) 0.6284(8) 0.3496(7) 0.057(3) Uiso 0.566(12) 1 d A 1 . C27B C 0.7070(8) 0.7253(6) 0.4222(7) 0.054(2) Uiso 0.566(12) 1 d A 1 . H27B H 0.7610 0.7284 0.4765 0.065 Uiso 0.566(12) 1 calc A 1 R C23B C 0.5996(10) 0.6228(9) 0.2673(8) 0.067(3) Uiso 0.566(12) 1 d A 1 . H23B H 0.5813 0.5571 0.2187 0.081 Uiso 0.566(12) 1 calc A 1 R C11 C 1.5624(4) 0.0971(3) 0.1820(3) 0.0644(10) Uani 1 1 d . . . C16 C 1.0494(5) 0.2609(3) 0.7771(3) 0.0747(11) Uani 1 1 d A . . H16 H 1.1206 0.3000 0.7654 0.090 Uiso 1 1 calc . . R C25B C 0.5846(7) 0.8102(7) 0.3252(7) 0.0566(19) Uiso 0.566(12) 1 d A 1 . C26B C 0.6588(8) 0.8182(6) 0.4090(7) 0.062(2) Uiso 0.566(12) 1 d A 1 . H26B H 0.6770 0.8846 0.4567 0.075 Uiso 0.566(12) 1 calc A 1 R O1 O 1.2102(2) 0.2366(2) 0.31488(18) 0.0622(7) Uani 1 1 d A . . C2 C 0.9431(3) 0.2274(3) 0.4210(2) 0.0503(8) Uani 1 1 d . . . C1 C 0.9766(3) 0.2649(3) 0.3472(2) 0.0517(8) Uani 1 1 d A . . C28 C 0.9972(4) 0.1224(3) 0.4226(3) 0.0592(9) Uani 1 1 d A . . H28A H 1.0104 0.1271 0.4897 0.071 Uiso 1 1 calc . . R H28B H 1.0857 0.1091 0.3928 0.071 Uiso 1 1 calc . . R C21A C 0.8354(12) 0.5432(8) 0.4343(7) 0.052(2) Uiso 0.434(12) 1 d A 2 . H21A H 0.9163 0.5804 0.4262 0.062 Uiso 0.434(12) 1 calc A 2 R H21B H 0.7997 0.5822 0.4978 0.062 Uiso 0.434(12) 1 calc A 2 R C7 C 1.0752(3) 0.2017(3) 0.2720(3) 0.0563(8) Uani 1 1 d . . . H7A H 1.0629 0.1261 0.2578 0.068 Uiso 1 1 calc A . R H7B H 1.0613 0.2156 0.2121 0.068 Uiso 1 1 calc . . R C32 C 0.9584(4) 0.4010(3) 0.2650(3) 0.0669(10) Uani 1 1 d A . . H32A H 1.0498 0.3787 0.2427 0.080 Uiso 1 1 calc . . R H32B H 0.9566 0.4781 0.2884 0.080 Uiso 1 1 calc . . R C6 C 0.9281(3) 0.3637(3) 0.3474(2) 0.0529(8) Uani 1 1 d . . . C33 C 0.8542(5) 0.3561(5) 0.1792(3) 0.0930(15) Uani 1 1 d . . . H33A H 0.8786 0.3792 0.1272 0.139 Uiso 1 1 calc A . GR H33B H 0.7643 0.3813 0.2001 0.139 Uiso 1 1 calc . . GR H33C H 0.8545 0.2798 0.1567 0.139 Uiso 1 1 calc . . GR C3B C 0.8352(10) 0.2816(12) 0.4884(11) 0.041(2) Uani 0.566(12) 1 d A 1 . C29 C 0.9005(5) 0.0293(3) 0.3688(4) 0.0786(12) Uani 1 1 d . . . H29A H 0.8897 0.0227 0.3017 0.118 Uiso 1 1 calc A . GR H29B H 0.8128 0.0419 0.3982 0.118 Uiso 1 1 calc . . GR H29C H 0.9381 -0.0351 0.3726 0.118 Uiso 1 1 calc . . GR C5B C 0.8272(11) 0.4195(12) 0.4193(12) 0.043(2) Uani 0.566(12) 1 d A 1 . C14B C 0.8060(8) 0.2415(5) 0.5664(5) 0.0441(17) Uiso 0.566(12) 1 d A 1 . H14A H 0.8046 0.1644 0.5410 0.053 Uiso 0.566(12) 1 calc A 1 R H14B H 0.7172 0.2662 0.5926 0.053 Uiso 0.566(12) 1 calc A 1 R C4A C 0.8411(12) 0.3966(9) 0.5066(8) 0.049(2) Uani 0.434(12) 1 d A 2 . C30A C 0.7614(9) 0.4684(7) 0.5970(8) 0.060(3) Uani 0.434(12) 1 d A 2 . H30A H 0.7787 0.4450 0.6515 0.072 Uiso 0.434(12) 1 calc A 2 R H30B H 0.7923 0.5417 0.6161 0.072 Uiso 0.434(12) 1 calc A 2 R C30B C 0.6632(10) 0.4267(6) 0.5488(6) 0.059(2) Uani 0.566(12) 1 d A 1 . H30C H 0.6121 0.4685 0.5177 0.071 Uiso 0.566(12) 1 calc A 1 R H30D H 0.6023 0.3707 0.5506 0.071 Uiso 0.566(12) 1 calc A 1 R C31B C 0.6978(9) 0.4962(6) 0.6505(6) 0.072(2) Uani 0.566(12) 1 d A 1 . H31A H 0.7559 0.5537 0.6506 0.108 Uiso 0.566(12) 1 calc A 1 GR H31B H 0.7449 0.4557 0.6837 0.108 Uiso 0.566(12) 1 calc A 1 GR H31C H 0.6152 0.5244 0.6832 0.108 Uiso 0.566(12) 1 calc A 1 GR C17 C 1.0638(5) 0.2218(3) 0.8525(3) 0.0746(11) Uani 1 1 d . . . H17 H 1.1442 0.2339 0.8909 0.089 Uiso 1 1 calc A . R C4B C 0.7810(9) 0.3747(7) 0.4842(6) 0.0482(19) Uani 0.566(12) 1 d A 1 . C24B C 0.5562(10) 0.7123(7) 0.2553(8) 0.074(3) Uiso 0.566(12) 1 d A 1 . H24B H 0.5062 0.7077 0.1989 0.088 Uiso 0.566(12) 1 calc A 1 R C31A C 0.6144(13) 0.4604(16) 0.5707(14) 0.098(5) Uani 0.434(12) 1 d A 2 . H31D H 0.5969 0.4900 0.5210 0.148 Uiso 0.434(12) 1 calc A 2 GR H31E H 0.5638 0.4990 0.6271 0.148 Uiso 0.434(12) 1 calc A 2 GR H31F H 0.5861 0.3871 0.5467 0.148 Uiso 0.434(12) 1 calc A 2 GR C3A C 0.8799(14) 0.2932(17) 0.4988(18) 0.047(3) Uani 0.434(12) 1 d A 2 . C5A C 0.8722(14) 0.4328(18) 0.4276(18) 0.047(3) Uani 0.434(12) 1 d A 2 . C14A C 0.8454(14) 0.2583(10) 0.5858(10) 0.066(3) Uiso 0.434(12) 1 d A 2 . H14C H 0.7648 0.2956 0.6172 0.079 Uiso 0.434(12) 1 calc A 2 R H14D H 0.8254 0.1826 0.5620 0.079 Uiso 0.434(12) 1 calc A 2 R C21B C 0.7910(9) 0.5334(6) 0.4339(6) 0.055(2) Uiso 0.566(12) 1 d A 1 . H21C H 0.7548 0.5674 0.4981 0.067 Uiso 0.566(12) 1 calc A 1 R H21D H 0.8732 0.5720 0.4302 0.067 Uiso 0.566(12) 1 calc A 1 R O2B O 0.9154(8) 0.2818(5) 0.6437(5) 0.0563(19) Uiso 0.566(12) 1 d A 1 . O3A O 0.7252(10) 0.5371(7) 0.3532(7) 0.064(3) Uiso 0.434(12) 1 d A 2 . C22A C 0.6740(11) 0.6421(9) 0.3694(7) 0.044(3) Uiso 0.434(12) 1 d A 2 . C27A C 0.6919(11) 0.7362(7) 0.4468(9) 0.053(3) Uiso 0.434(12) 1 d A 2 . H27A H 0.7367 0.7354 0.5034 0.064 Uiso 0.434(12) 1 calc A 2 R C26A C 0.6461(9) 0.8311(7) 0.4435(8) 0.054(2) Uiso 0.434(12) 1 d A 2 . H26A H 0.6630 0.8938 0.4962 0.064 Uiso 0.434(12) 1 calc A 2 R C25A C 0.5749(7) 0.8333(6) 0.3620(6) 0.040(2) Uiso 0.434(12) 1 d A 2 . C24A C 0.5464(9) 0.7404(7) 0.2827(7) 0.047(2) Uiso 0.434(12) 1 d A 2 . H24A H 0.4981 0.7419 0.2276 0.056 Uiso 0.434(12) 1 calc A 2 R C23A C 0.5935(11) 0.6439(9) 0.2890(8) 0.052(3) Uiso 0.434(12) 1 d A 2 . H23A H 0.5708 0.5802 0.2388 0.063 Uiso 0.434(12) 1 calc A 2 R Cl3A Cl 0.5132(19) 0.9498(12) 0.3520(13) 0.110(3) Uani 0.434(12) 1 d A 2 . 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 Cl2 0.1290(10) 0.1069(10) 0.0757(7) 0.0533(7) 0.0101(7) 0.0146(8) Cl1 0.0638(6) 0.1380(12) 0.0947(8) 0.0338(8) 0.0203(6) 0.0271(7) Cl3B 0.085(4) 0.109(6) 0.244(11) 0.133(7) -0.045(6) -0.015(4) C9 0.0557(19) 0.061(2) 0.058(2) 0.0187(17) 0.0035(16) -0.0042(16) C8 0.0495(17) 0.0503(19) 0.0521(18) 0.0182(15) 0.0066(14) 0.0006(14) C15 0.074(2) 0.0477(19) 0.060(2) 0.0268(16) 0.0219(18) 0.0081(16) C19 0.067(2) 0.082(3) 0.095(3) 0.053(3) 0.020(2) 0.009(2) C18 0.084(3) 0.059(2) 0.058(2) 0.0282(18) 0.0157(19) 0.0127(19) C10 0.068(2) 0.068(2) 0.0547(19) 0.0182(18) 0.0128(17) 0.0063(18) C12 0.053(2) 0.087(3) 0.071(2) 0.029(2) -0.0001(18) 0.0017(19) C13 0.060(2) 0.071(3) 0.062(2) 0.0081(19) -0.0003(17) 0.0008(18) C20 0.063(2) 0.072(2) 0.078(2) 0.045(2) 0.0148(18) 0.0063(18) C11 0.0512(19) 0.084(3) 0.065(2) 0.035(2) 0.0093(17) 0.0083(18) C16 0.083(3) 0.065(3) 0.074(3) 0.022(2) 0.008(2) -0.016(2) O1 0.0480(12) 0.0633(15) 0.0604(14) 0.0038(12) 0.0052(10) 0.0013(11) C2 0.0563(18) 0.0410(17) 0.0550(18) 0.0188(15) 0.0046(15) 0.0031(14) C1 0.0520(17) 0.0460(18) 0.0553(18) 0.0158(15) 0.0021(14) 0.0035(14) C28 0.0545(18) 0.051(2) 0.074(2) 0.0241(17) 0.0011(16) 0.0119(15) C7 0.0481(17) 0.057(2) 0.060(2) 0.0164(17) 0.0020(15) 0.0028(15) C32 0.066(2) 0.071(3) 0.076(2) 0.040(2) 0.0104(19) 0.0049(18) C6 0.0601(19) 0.0508(19) 0.0511(18) 0.0221(15) 0.0036(15) -0.0010(15) C33 0.097(3) 0.123(4) 0.063(2) 0.040(3) -0.008(2) 0.012(3) C3B 0.036(6) 0.038(4) 0.053(5) 0.020(4) 0.008(5) 0.001(5) C29 0.092(3) 0.042(2) 0.098(3) 0.019(2) -0.001(2) 0.0001(19) C5B 0.041(6) 0.036(5) 0.057(5) 0.023(4) 0.003(6) 0.002(5) C4A 0.042(6) 0.056(6) 0.054(6) 0.024(5) 0.008(5) 0.004(5) C30A 0.047(5) 0.053(5) 0.080(7) 0.024(5) 0.000(5) -0.001(4) C30B 0.052(6) 0.050(4) 0.076(5) 0.023(4) 0.015(4) 0.019(4) C31B 0.070(5) 0.064(5) 0.075(5) 0.014(4) 0.023(4) 0.013(4) C17 0.085(3) 0.067(3) 0.066(2) 0.016(2) -0.002(2) -0.007(2) C4B 0.042(4) 0.047(4) 0.057(4) 0.020(3) 0.004(4) 0.008(3) C31A 0.040(6) 0.116(13) 0.145(14) 0.052(11) 0.025(7) 0.022(6) C3A 0.030(7) 0.050(7) 0.071(8) 0.036(6) 0.000(6) -0.006(6) C5A 0.033(7) 0.043(6) 0.071(7) 0.029(5) -0.003(7) -0.007(6) Cl3A 0.087(4) 0.078(3) 0.186(8) 0.076(4) -0.021(4) 0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl2 C18 1.754(4) . ? Cl1 C11 1.746(4) . ? Cl3B C25B 1.750(13) . ? O2A C15 1.312(8) . ? O2A C14A 1.334(16) . ? C9 H9 0.9300 . ? C9 C8 1.372(5) . ? C9 C10 1.398(5) . ? O3B C22B 1.356(12) . ? O3B C21B 1.330(10) . ? C8 C13 1.389(5) . ? C8 O1 1.375(4) . ? C15 C20 1.368(5) . ? C15 C16 1.385(6) . ? C15 O2B 1.394(7) . ? C19 H19 0.9300 . ? C19 C18 1.376(6) . ? C19 C20 1.391(5) . ? C18 C17 1.366(6) . ? C10 H10 0.9300 . ? C10 C11 1.360(5) . ? C12 H12 0.9300 . ? C12 C13 1.377(6) . ? C12 C11 1.374(6) . ? C13 H13 0.9300 . ? C20 H20 0.9300 . ? C22B C27B 1.398(10) . ? C22B C23B 1.347(10) . ? C27B H27B 0.9300 . ? C27B C26B 1.410(8) . ? C23B H23B 0.9300 . ? C23B C24B 1.343(10) . ? C16 H16 0.9300 . ? C16 C17 1.391(6) . ? C25B C26B 1.378(9) . ? C25B C24B 1.373(10) . ? C26B H26B 0.9300 . ? O1 C7 1.444(4) . ? C2 C1 1.399(5) . ? C2 C28 1.517(5) . ? C2 C3B 1.476(14) . ? C2 C3A 1.34(2) . ? C1 C7 1.506(5) . ? C1 C6 1.410(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C29 1.526(5) . ? C21A H21A 0.9700 . ? C21A H21B 0.9700 . ? C21A C5A 1.50(2) . ? C21A O3A 1.557(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C6 1.507(5) . ? C32 C33 1.535(6) . ? C6 C5B 1.468(16) . ? C6 C5A 1.35(3) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C3B C14B 1.468(16) . ? C3B C4B 1.379(16) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C5B C4B 1.386(16) . ? C5B C21B 1.514(17) . ? C14B H14A 0.9700 . ? C14B H14B 0.9700 . ? C14B O2B 1.484(10) . ? C4A C30A 1.568(16) . ? C4A C3A 1.41(2) . ? C4A C5A 1.45(2) . ? C30A H30A 0.9700 . ? C30A H30B 0.9700 . ? C30A C31A 1.467(16) . ? C30B H30C 0.9700 . ? C30B H30D 0.9700 . ? C30B C31B 1.481(12) . ? C30B C4B 1.521(13) . ? C31B H31A 0.9600 . ? C31B H31B 0.9600 . ? C31B H31C 0.9600 . ? C17 H17 0.9300 . ? C24B H24B 0.9300 . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? C3A C14A 1.56(2) . ? C14A H14C 0.9700 . ? C14A H14D 0.9700 . ? C21B H21C 0.9700 . ? C21B H21D 0.9700 . ? O3A C22A 1.438(15) . ? C22A C27A 1.373(11) . ? C22A C23A 1.404(11) . ? C27A H27A 0.9300 . ? C27A C26A 1.369(10) . ? C26A H26A 0.9300 . ? C26A C25A 1.373(10) . ? C25A C24A 1.392(10) . ? C25A Cl3A 1.732(18) . ? C24A H24A 0.9300 . ? C24A C23A 1.409(10) . ? C23A H23A 0.9300 . ? 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 C15 O2A C14A 111.1(8) . . ? C8 C9 H9 120.4 . . ? C8 C9 C10 119.2(3) . . ? C10 C9 H9 120.4 . . ? C21B O3B C22B 123.4(7) . . ? C9 C8 C13 119.8(3) . . ? C9 C8 O1 125.2(3) . . ? O1 C8 C13 114.9(3) . . ? O2A C15 C20 133.7(6) . . ? O2A C15 C16 106.9(5) . . ? O2A C15 O2B 15.0(5) . . ? C20 C15 C16 119.2(3) . . ? C20 C15 O2B 119.8(5) . . ? C16 C15 O2B 120.9(4) . . ? C18 C19 H19 120.4 . . ? C18 C19 C20 119.3(4) . . ? C20 C19 H19 120.4 . . ? C19 C18 Cl2 118.9(3) . . ? C17 C18 Cl2 119.8(3) . . ? C17 C18 C19 121.3(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 C9 120.1(4) . . ? C11 C10 H10 119.9 . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C11 C12 C13 119.1(4) . . ? C8 C13 H13 119.7 . . ? C12 C13 C8 120.6(4) . . ? C12 C13 H13 119.7 . . ? C15 C20 C19 120.5(4) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? O3B C22B C27B 117.8(7) . . ? C23B C22B O3B 119.8(8) . . ? C23B C22B C27B 122.3(9) . . ? C22B C27B H27B 121.6 . . ? C22B C27B C26B 116.8(7) . . ? C26B C27B H27B 121.6 . . ? C22B C23B H23B 120.0 . . ? C24B C23B C22B 120.0(10) . . ? C24B C23B H23B 120.0 . . ? C10 C11 Cl1 119.2(3) . . ? C10 C11 C12 121.1(4) . . ? C12 C11 Cl1 119.7(3) . . ? C15 C16 H16 119.6 . . ? C15 C16 C17 120.8(4) . . ? C17 C16 H16 119.6 . . ? C26B C25B Cl3B 116.0(7) . . ? C24B C25B Cl3B 123.8(7) . . ? C24B C25B C26B 120.2(7) . . ? C27B C26B H26B 120.2 . . ? C25B C26B C27B 119.6(7) . . ? C25B C26B H26B 120.2 . . ? C8 O1 C7 118.6(2) . . ? C1 C2 C28 121.3(3) . . ? C1 C2 C3B 119.0(6) . . ? C3B C2 C28 118.9(6) . . ? C3A C2 C1 118.6(9) . . ? C3A C2 C28 119.3(9) . . ? C3A C2 C3B 18.2(8) . . ? C2 C1 C7 118.5(3) . . ? C2 C1 C6 120.8(3) . . ? C6 C1 C7 120.5(3) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? C2 C28 C29 112.4(3) . . ? H28A C28 H28B 107.9 . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? H21A C21A H21B 108.3 . . ? C5A C21A H21A 109.8 . . ? C5A C21A H21B 109.8 . . ? C5A C21A O3A 109.3(10) . . ? O3A C21A H21A 109.8 . . ? O3A C21A H21B 109.8 . . ? O1 C7 C1 105.4(3) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.9 . . ? C6 C32 H32A 109.3 . . ? C6 C32 H32B 109.3 . . ? C6 C32 C33 111.7(3) . . ? C33 C32 H32A 109.3 . . ? C33 C32 H32B 109.3 . . ? C1 C6 C32 120.5(3) . . ? C1 C6 C5B 118.2(6) . . ? C5B C6 C32 120.3(6) . . ? C5A C6 C1 120.2(9) . . ? C5A C6 C32 118.5(9) . . ? C5A C6 C5B 18.6(8) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C14B C3B C2 117.2(10) . . ? C4B C3B C2 119.2(10) . . ? C4B C3B C14B 123.0(11) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 119.8(9) . . ? C4B C5B C6 120.2(11) . . ? C4B C5B C21B 119.3(12) . . ? C3B C14B H14A 110.1 . . ? C3B C14B H14B 110.1 . . ? C3B C14B O2B 107.9(6) . . ? H14A C14B H14B 108.4 . . ? O2B C14B H14A 110.1 . . ? O2B C14B H14B 110.1 . . ? C3A C4A C30A 120.1(12) . . ? C3A C4A C5A 118.5(16) . . ? C5A C4A C30A 121.4(12) . . ? C4A C30A H30A 110.0 . . ? C4A C30A H30B 110.0 . . ? H30A C30A H30B 108.3 . . ? C31A C30A C4A 108.7(13) . . ? C31A C30A H30A 110.0 . . ? C31A C30A H30B 110.0 . . ? H30C C30B H30D 107.2 . . ? C31B C30B H30C 107.9 . . ? C31B C30B H30D 107.9 . . ? C31B C30B C4B 117.6(9) . . ? C4B C30B H30C 107.9 . . ? C4B C30B H30D 107.9 . . ? C18 C17 C16 118.9(4) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C3B C4B C5B 121.6(10) . . ? C3B C4B C30B 119.3(8) . . ? C5B C4B C30B 119.0(9) . . ? C23B C24B C25B 120.9(8) . . ? C23B C24B H24B 119.5 . . ? C25B C24B H24B 119.5 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 122.1(16) . . ? C2 C3A C14A 121.3(15) . . ? C4A C3A C14A 116.5(17) . . ? C6 C5A C21A 121.3(16) . . ? C6 C5A C4A 118.6(16) . . ? C4A C5A C21A 120.0(18) . . ? O2A C14A C3A 109.9(9) . . ? O2A C14A H14C 109.7 . . ? O2A C14A H14D 109.7 . . ? C3A C14A H14C 109.7 . . ? C3A C14A H14D 109.7 . . ? H14C C14A H14D 108.2 . . ? O3B C21B C5B 111.2(8) . . ? O3B C21B H21C 109.4 . . ? O3B C21B H21D 109.4 . . ? C5B C21B H21C 109.4 . . ? C5B C21B H21D 109.4 . . ? H21C C21B H21D 108.0 . . ? C15 O2B C14B 121.5(5) . . ? C22A O3A C21A 109.1(8) . . ? C27A C22A O3A 131.5(9) . . ? C27A C22A C23A 117.5(9) . . ? C23A C22A O3A 111.0(9) . . ? C22A C27A H27A 118.9 . . ? C26A C27A C22A 122.3(9) . . ? C26A C27A H27A 118.9 . . ? C27A C26A H26A 120.1 . . ? C27A C26A C25A 119.8(9) . . ? C25A C26A H26A 120.1 . . ? C26A C25A C24A 121.2(7) . . ? C26A C25A Cl3A 122.7(9) . . ? C24A C25A Cl3A 116.1(8) . . ? C25A C24A H24A 121.2 . . ? C25A C24A C23A 117.6(8) . . ? C23A C24A H24A 121.2 . . ? C22A C23A C24A 121.3(9) . . ? C22A C23A H23A 119.4 . . ? C24A C23A H23A 119.4 . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C18 C17 C16 177.5(3) . . . . ? Cl3B C25B C26B C27B -179.6(7) . . . . ? Cl3B C25B C24B C23B -179.4(9) . . . . ? O2A C15 C20 C19 173.4(7) . . . . ? O2A C15 C16 C17 -174.6(6) . . . . ? O2A C15 O2B C14B 143(3) . . . . ? C9 C8 C13 C12 0.3(6) . . . . ? C9 C8 O1 C7 0.1(5) . . . . ? C9 C10 C11 Cl1 -178.7(3) . . . . ? C9 C10 C11 C12 0.7(6) . . . . ? O3B C22B C27B C26B -171.2(8) . . . . ? O3B C22B C23B C24B 172.0(9) . . . . ? C8 C9 C10 C11 -2.2(6) . . . . ? C8 O1 C7 C1 175.6(3) . . . . ? C15 O2A C14A C3A -173.8(11) . . . . ? C15 C16 C17 C18 -0.6(6) . . . . ? C19 C18 C17 C16 0.3(6) . . . . ? C18 C19 C20 C15 -0.2(6) . . . . ? C10 C9 C8 C13 1.7(5) . . . . ? C10 C9 C8 O1 -177.4(3) . . . . ? C13 C8 O1 C7 -179.0(3) . . . . ? C13 C12 C11 Cl1 -179.2(3) . . . . ? C13 C12 C11 C10 1.3(6) . . . . ? C20 C15 C16 C17 0.5(6) . . . . ? C20 C15 O2B C14B -16.1(8) . . . . ? C20 C19 C18 Cl2 -177.1(3) . . . . ? C20 C19 C18 C17 0.1(6) . . . . ? C22B O3B C21B C5B -165.5(9) . . . . ? C22B C27B C26B C25B -3.1(12) . . . . ? C22B C23B C24B C25B 1.4(15) . . . . ? C27B C22B C23B C24B -4.0(15) . . . . ? C23B C22B C27B C26B 4.8(14) . . . . ? C11 C12 C13 C8 -1.8(7) . . . . ? C16 C15 C20 C19 -0.1(6) . . . . ? C16 C15 O2B C14B 164.6(5) . . . . ? C26B C25B C24B C23B 0.1(13) . . . . ? O1 C8 C13 C12 179.5(4) . . . . ? C2 C1 C7 O1 -84.8(4) . . . . ? C2 C1 C6 C32 -176.8(3) . . . . ? C2 C1 C6 C5B -7.9(7) . . . . ? C2 C1 C6 C5A 13.3(8) . . . . ? C2 C3B C14B O2B 77.8(10) . . . . ? C2 C3B C4B C5B -1.2(15) . . . . ? C2 C3B C4B C30B 175.9(9) . . . . ? C2 C3A C14A O2A 88.0(14) . . . . ? C1 C2 C28 C29 -91.2(4) . . . . ? C1 C2 C3B C14B -178.3(6) . . . . ? C1 C2 C3B C4B -7.2(12) . . . . ? C1 C2 C3A C4A 2.9(14) . . . . ? C1 C2 C3A C14A -177.3(8) . . . . ? C1 C6 C5B C4B -0.6(12) . . . . ? C1 C6 C5B C21B 169.4(7) . . . . ? C1 C6 C5A C21A 172.5(8) . . . . ? C1 C6 C5A C4A -10.7(13) . . . . ? C28 C2 C1 C7 -3.6(5) . . . . ? C28 C2 C1 C6 -178.7(3) . . . . ? C28 C2 C3B C14B 11.9(11) . . . . ? C28 C2 C3B C4B -177.0(7) . . . . ? C28 C2 C3A C4A 172.7(8) . . . . ? C28 C2 C3A C14A -7.4(13) . . . . ? C21A O3A C22A C27A -10.1(16) . . . . ? C21A O3A C22A C23A 169.2(9) . . . . ? C7 C1 C6 C32 8.3(5) . . . . ? C7 C1 C6 C5B 177.1(6) . . . . ? C7 C1 C6 C5A -161.7(7) . . . . ? C32 C6 C5B C4B 168.3(7) . . . . ? C32 C6 C5B C21B -21.7(12) . . . . ? C32 C6 C5A C21A 2.4(13) . . . . ? C32 C6 C5A C4A 179.2(8) . . . . ? C6 C1 C7 O1 90.3(4) . . . . ? C6 C5B C4B C3B 5.0(15) . . . . ? C6 C5B C4B C30B -172.0(9) . . . . ? C6 C5B C21B O3B 81.9(10) . . . . ? C33 C32 C6 C1 84.9(4) . . . . ? C33 C32 C6 C5B -83.8(7) . . . . ? C33 C32 C6 C5A -105.1(8) . . . . ? C3B C2 C1 C7 -173.2(6) . . . . ? C3B C2 C1 C6 11.8(7) . . . . ? C3B C2 C28 C29 78.4(7) . . . . ? C3B C2 C3A C4A -93(5) . . . . ? C3B C2 C3A C14A 86(4) . . . . ? C3B C14B O2B C15 -168.4(7) . . . . ? C5B C6 C5A C21A -98(5) . . . . ? C5B C6 C5A C4A 79(4) . . . . ? C14B C3B C4B C5B 169.4(10) . . . . ? C14B C3B C4B C30B -13.6(14) . . . . ? C4A C3A C14A O2A -92.1(12) . . . . ? C30A C4A C3A C2 177.2(10) . . . . ? C30A C4A C3A C14A -2.7(16) . . . . ? C30A C4A C5A C21A 3.6(17) . . . . ? C30A C4A C5A C6 -173.2(10) . . . . ? C31B C30B C4B C3B 83.3(11) . . . . ? C31B C30B C4B C5B -99.5(10) . . . . ? C4B C3B C14B O2B -92.9(9) . . . . ? C4B C5B C21B O3B -108.0(11) . . . . ? C24B C25B C26B C27B 0.8(12) . . . . ? C3A C2 C1 C7 166.0(7) . . . . ? C3A C2 C1 C6 -9.1(8) . . . . ? C3A C2 C28 C29 99.3(8) . . . . ? C3A C2 C3B C14B -85(4) . . . . ? C3A C2 C3B C4B 87(4) . . . . ? C3A C4A C30A C31A -97.1(12) . . . . ? C3A C4A C5A C21A -178.6(10) . . . . ? C3A C4A C5A C6 4.6(16) . . . . ? C5A C21A O3A C22A 170.8(11) . . . . ? C5A C6 C5B C4B -102(5) . . . . ? C5A C6 C5B C21B 68(4) . . . . ? C5A C4A C30A C31A 80.6(14) . . . . ? C5A C4A C3A C2 -0.6(16) . . . . ? C5A C4A C3A C14A 179.5(10) . . . . ? C14A O2A C15 C20 0.9(13) . . . . ? C14A O2A C15 C16 175.0(8) . . . . ? C14A O2A C15 O2B -24(2) . . . . ? C21B O3B C22B C27B -19.1(13) . . . . ? C21B O3B C22B C23B 164.8(9) . . . . ? C21B C5B C4B C3B -165.0(9) . . . . ? C21B C5B C4B C30B 18.0(14) . . . . ? O2B C15 C20 C19 -179.4(5) . . . . ? O2B C15 C16 C17 179.8(5) . . . . ? O3A C21A C5A C6 61.6(13) . . . . ? O3A C21A C5A C4A -115.2(12) . . . . ? O3A C22A C27A C26A 172.6(11) . . . . ? O3A C22A C23A C24A -172.0(10) . . . . ? C22A C27A C26A C25A 2.6(16) . . . . ? C27A C22A C23A C24A 7.4(16) . . . . ? C27A C26A C25A C24A 1.0(14) . . . . ? C27A C26A C25A Cl3A 179.9(10) . . . . ? C26A C25A C24A C23A -0.1(12) . . . . ? C25A C24A C23A C22A -4.1(14) . . . . ? C23A C22A C27A C26A -6.6(16) . . . . ? Cl3A C25A C24A C23A -179.1(9) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.046 0.000 0.500 389 27 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962428' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-ea-118K _audit_creation_date 2013-12-23 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-ea, 118 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Br3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Br3 O5' _chemical_formula_weight 805.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.6357(4) _cell_length_b 13.3206(6) _cell_length_c 14.8618(8) _cell_angle_alpha 111.930(5) _cell_angle_beta 93.132(4) _cell_angle_gamma 90.688(3) _cell_volume 1765.81(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5714 _cell_measurement_temperature 118(2) _cell_measurement_theta_max 29.0557 _cell_measurement_theta_min 3.7341 _exptl_absorpt_coefficient_mu 3.467 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.54954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_unetI/netI 0.0517 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 24432 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.12 _diffrn_reflns_theta_min 3.74 _diffrn_ambient_temperature 118(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.878 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0462313000 _diffrn_orient_matrix_UB_12 0.0458531000 _diffrn_orient_matrix_UB_13 0.0198938000 _diffrn_orient_matrix_UB_21 0.0097212000 _diffrn_orient_matrix_UB_22 -0.0102223000 _diffrn_orient_matrix_UB_23 0.0434222000 _diffrn_orient_matrix_UB_31 0.0566547000 _diffrn_orient_matrix_UB_32 -0.0330456000 _diffrn_orient_matrix_UB_33 -0.0194053000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6105 _reflns_number_total 8345 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.081 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.097 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 373 _refine_ls_number_reflns 8345 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0468 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1286 _refine_ls_wR_factor_ref 0.1393 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uiso(C25B) = Uiso(C25A) Uiso(C26B) = Uiso(C26A) Uiso(C24B) = Uiso(C24A) Uiso(C30B) = Uiso(C30A) Uiso(C31A) = Uiso(C31B) Uiso(C27A) = Uiso(C27B) Uiso(C22A) = Uiso(C22B) Uiso(C23A) = Uiso(C23B) 4. Others Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(Br3A)=Sof(C27A)=Sof(H27A)=Sof(C23A)=Sof(H23A)=Sof(C25A)= Sof(C26A)=Sof(H26A)=Sof(C24A)=Sof(H24A)=Sof(C5A)=Sof(C3A)=Sof(C21A)=Sof(H21C)= Sof(H21D)=Sof(O3A)=Sof(C22A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(O2A)=1-FVAR(1) Sof(O2B)=Sof(O3B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C22B)=Sof(Br3B)=Sof(C24B)=Sof(H24B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C23B)=Sof(H23B)=Sof(C27B)=Sof(H27B)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 5.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C16(H16), C17(H17), C27A(H27A), C23A(H23A), C24B(H24B), C26A(H26A), C26B(H26B), C24A(H24A), C23B(H23B), C27B(H27B) 5.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.98786(4) 0.12147(3) 0.97189(2) 0.03429(12) Uani 1 1 d . . . Br1 Br 1.72338(3) 0.03634(3) 0.12656(3) 0.03967(13) Uani 1 1 d . . . O2B O 0.9226(7) 0.2824(5) 0.6413(5) 0.0248(13) Uani 0.688(4) 1 d A 1 . C9 C 1.3093(3) 0.1067(3) 0.1776(2) 0.0267(7) Uani 1 1 d . . . H9 H 1.2210 0.0801 0.1450 0.032 Uiso 1 1 calc . . R O3B O 0.6863(9) 0.5358(8) 0.3623(7) 0.0289(15) Uani 0.688(4) 1 d A 1 . C8 C 1.3187(3) 0.1914(3) 0.2675(2) 0.0233(7) Uani 1 1 d . . . C15 C 0.9362(3) 0.2467(3) 0.7180(2) 0.0259(7) Uani 1 1 d . . . C19 C 0.8424(3) 0.1541(3) 0.8133(3) 0.0291(7) Uani 1 1 d . . . H19 H 0.7681 0.1154 0.8267 0.035 Uiso 1 1 calc A . R C18 C 0.9671(3) 0.1752(3) 0.8698(2) 0.0253(7) Uani 1 1 d A . . C10 C 1.4309(3) 0.0610(3) 0.1357(2) 0.0299(8) Uani 1 1 d . . . H10 H 1.4259 0.0022 0.0747 0.036 Uiso 1 1 calc . . R C12 C 1.5687(3) 0.1874(3) 0.2727(3) 0.0291(7) Uani 1 1 d . . . H12 H 1.6571 0.2149 0.3045 0.035 Uiso 1 1 calc . . R C13 C 1.4492(3) 0.2318(3) 0.3142(2) 0.0284(7) Uani 1 1 d . . . H13 H 1.4549 0.2905 0.3753 0.034 Uiso 1 1 calc . . R C20 C 0.8278(3) 0.1900(3) 0.7375(3) 0.0285(7) Uani 1 1 d A . . H20 H 0.7430 0.1758 0.6985 0.034 Uiso 1 1 calc . . R C11 C 1.5587(3) 0.1015(3) 0.1833(2) 0.0276(7) Uani 1 1 d . . . C16 C 1.0607(4) 0.2691(3) 0.7764(3) 0.0305(8) Uani 1 1 d A . . H16 H 1.1343 0.3092 0.7639 0.037 Uiso 1 1 calc . . R O1 O 1.2065(2) 0.24048(18) 0.31663(16) 0.0255(5) Uani 1 1 d A . . C2 C 0.9402(3) 0.2266(2) 0.4206(2) 0.0241(7) Uani 1 1 d . . . C1 C 0.9702(3) 0.2648(2) 0.3484(2) 0.0225(7) Uani 1 1 d A . . C28 C 1.0037(3) 0.1239(3) 0.4242(3) 0.0278(7) Uani 1 1 d A . . H28A H 1.0206 0.1320 0.4929 0.033 Uiso 1 1 calc . . R H28B H 1.0945 0.1141 0.3945 0.033 Uiso 1 1 calc . . R C21B C 0.7862(6) 0.5346(5) 0.4367(4) 0.0222(14) Uiso 0.688(4) 1 d A 1 . H21A H 0.7476 0.5695 0.5010 0.027 Uiso 0.688(4) 1 calc A 1 R H21B H 0.8711 0.5765 0.4355 0.027 Uiso 0.688(4) 1 calc A 1 R C7 C 1.0680(3) 0.2030(3) 0.2730(2) 0.0257(7) Uani 1 1 d . . . H7A H 1.0554 0.1241 0.2565 0.031 Uiso 1 1 calc A . R H7B H 1.0514 0.2181 0.2130 0.031 Uiso 1 1 calc . . R C32 C 0.9479(3) 0.4049(3) 0.2694(2) 0.0271(7) Uani 1 1 d A . . H32A H 1.0412 0.3826 0.2461 0.032 Uiso 1 1 calc . . R H32B H 0.9478 0.4850 0.2957 0.032 Uiso 1 1 calc . . R C6 C 0.9189(3) 0.3642(3) 0.3496(2) 0.0229(7) Uani 1 1 d . . . C33 C 0.8384(4) 0.3600(3) 0.1837(3) 0.0382(9) Uani 1 1 d . . . H33A H 0.8590 0.3885 0.1337 0.057 Uiso 1 1 calc A . GR H33B H 0.7460 0.3821 0.2066 0.057 Uiso 1 1 calc . . GR H33C H 0.8406 0.2808 0.1562 0.057 Uiso 1 1 calc . . GR C3B C 0.8362(7) 0.2800(5) 0.4878(5) 0.0195(13) Uani 0.688(4) 1 d A 1 . C29 C 0.9095(4) 0.0231(3) 0.3707(3) 0.0366(9) Uani 1 1 d . . . H29A H 0.8999 0.0107 0.3013 0.055 Uiso 1 1 calc A . GR H29B H 0.8177 0.0342 0.3974 0.055 Uiso 1 1 calc . . GR H29C H 0.9508 -0.0399 0.3791 0.055 Uiso 1 1 calc . . GR C5B C 0.8227(7) 0.4208(5) 0.4220(5) 0.0188(13) Uani 0.688(4) 1 d A 1 . C14B C 0.8069(7) 0.2401(5) 0.5671(5) 0.0233(16) Uani 0.688(4) 1 d A 1 . H14A H 0.7174 0.2672 0.5949 0.028 Uiso 0.688(4) 1 calc A 1 R H14B H 0.8022 0.1600 0.5416 0.028 Uiso 0.688(4) 1 calc A 1 R C4A C 0.8373(14) 0.3967(10) 0.5056(9) 0.032(3) Uani 0.312(4) 1 d A 2 . C30A C 0.7659(9) 0.4653(8) 0.5942(7) 0.0197(8) Uiso 0.312(4) 1 d A 2 . H30A H 0.7889 0.4407 0.6482 0.024 Uiso 0.312(4) 1 calc A 2 R H30B H 0.7989 0.5417 0.6146 0.024 Uiso 0.312(4) 1 calc A 2 R C30B C 0.6600(5) 0.4239(4) 0.5504(3) 0.0197(8) Uiso 0.688(4) 1 d A 1 . H30C H 0.5983 0.3643 0.5512 0.024 Uiso 0.688(4) 1 calc A 1 R H30D H 0.6051 0.4664 0.5199 0.024 Uiso 0.688(4) 1 calc A 1 R C31B C 0.7014(5) 0.4976(4) 0.6561(3) 0.0238(9) Uiso 0.688(4) 1 d A 1 . H31A H 0.7545 0.5612 0.6571 0.036 Uiso 0.688(4) 1 calc A 1 GR H31B H 0.7586 0.4577 0.6870 0.036 Uiso 0.688(4) 1 calc A 1 GR H31C H 0.6174 0.5209 0.6916 0.036 Uiso 0.688(4) 1 calc A 1 GR C17 C 1.0765(4) 0.2329(3) 0.8519(3) 0.0308(8) Uani 1 1 d . . . H17 H 1.1610 0.2472 0.8912 0.037 Uiso 1 1 calc A . R C4B C 0.7776(5) 0.3746(4) 0.4869(4) 0.0162(11) Uiso 0.688(4) 1 d A 1 . C31A C 0.6165(11) 0.4573(10) 0.5728(8) 0.0238(9) Uiso 0.312(4) 1 d A 2 . H31D H 0.5951 0.4712 0.5134 0.036 Uiso 0.312(4) 1 calc A 2 GR H31E H 0.5717 0.5108 0.6270 0.036 Uiso 0.312(4) 1 calc A 2 GR H31F H 0.5818 0.3844 0.5636 0.036 Uiso 0.312(4) 1 calc A 2 GR C22B C 0.6606(6) 0.6280(4) 0.3540(4) 0.0227(9) Uiso 0.688(4) 1 d A 1 . Br3B Br 0.52237(16) 0.94696(19) 0.3186(3) 0.0943(8) Uani 0.688(4) 1 d A 1 . Br3A Br 0.5076(3) 0.9730(3) 0.36684(19) 0.0435(6) Uani 0.312(4) 1 d A 2 . C27A C 0.6896(13) 0.7453(8) 0.4578(9) 0.0261(10) Uiso 0.312(4) 1 d A 2 . H27A H 0.7383 0.7428 0.5142 0.031 Uiso 0.312(4) 1 calc A 2 R C23A C 0.5844(13) 0.6558(10) 0.2959(9) 0.0299(11) Uiso 0.312(4) 1 d A 2 . H23A H 0.5577 0.5908 0.2428 0.036 Uiso 0.312(4) 1 calc A 2 R C24B C 0.5443(6) 0.7204(4) 0.2627(4) 0.0324(11) Uiso 0.688(4) 1 d A 1 . H24B H 0.4916 0.7182 0.2060 0.039 Uiso 0.688(4) 1 calc A 1 R C25A C 0.5699(12) 0.8456(9) 0.3763(8) 0.0301(10) Uiso 0.312(4) 1 d A 2 . C26A C 0.6446(12) 0.8427(10) 0.4562(9) 0.0323(11) Uiso 0.312(4) 1 d A 2 . H26A H 0.6657 0.9078 0.5106 0.039 Uiso 0.312(4) 1 calc A 2 R C25B C 0.5779(5) 0.8193(5) 0.3369(4) 0.0301(10) Uiso 0.688(4) 1 d A 1 . C26B C 0.6535(6) 0.8236(5) 0.4192(4) 0.0323(11) Uiso 0.688(4) 1 d A 1 . H26B H 0.6769 0.8915 0.4699 0.039 Uiso 0.688(4) 1 calc A 1 R C24A C 0.5459(13) 0.7565(9) 0.2946(9) 0.0324(11) Uiso 0.312(4) 1 d A 2 . H24A H 0.5039 0.7619 0.2373 0.039 Uiso 0.312(4) 1 calc A 2 R C23B C 0.5869(6) 0.6244(5) 0.2703(4) 0.0299(11) Uiso 0.688(4) 1 d A 1 . H23B H 0.5655 0.5570 0.2186 0.036 Uiso 0.688(4) 1 calc A 1 R C27B C 0.6957(6) 0.7285(4) 0.4282(4) 0.0261(10) Uiso 0.688(4) 1 d A 1 . H27B H 0.7488 0.7314 0.4850 0.031 Uiso 0.688(4) 1 calc A 1 R C5A C 0.8630(14) 0.4306(14) 0.4297(12) 0.019(4) Uiso 0.312(4) 1 d A 2 . C3A C 0.8742(14) 0.2911(13) 0.4997(12) 0.017(4) Uiso 0.312(4) 1 d A 2 . C21A C 0.8269(14) 0.5423(10) 0.4376(9) 0.021(3) Uiso 0.312(4) 1 d A 2 . H21C H 0.7936 0.5831 0.5028 0.025 Uiso 0.312(4) 1 calc A 2 R H21D H 0.9107 0.5811 0.4295 0.025 Uiso 0.312(4) 1 calc A 2 R O3A O 0.7163(18) 0.5364(18) 0.3613(16) 0.023(4) Uiso 0.312(4) 1 d A 2 . C22A C 0.6637(12) 0.6528(10) 0.3778(8) 0.0227(9) Uiso 0.312(4) 1 d A 2 . C14A C 0.8422(15) 0.2529(13) 0.5802(12) 0.014(4) Uiso 0.312(4) 1 d A 2 . H14C H 0.7547 0.2839 0.6091 0.017 Uiso 0.312(4) 1 calc A 2 R H14D H 0.8317 0.1729 0.5548 0.017 Uiso 0.312(4) 1 calc A 2 R O2A O 0.9550(15) 0.2887(15) 0.6506(14) 0.027(4) Uiso 0.312(4) 1 d A 2 . 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 Br2 0.0391(2) 0.0443(2) 0.02350(18) 0.01645(16) 0.00687(14) 0.00961(16) Br1 0.02096(18) 0.0498(3) 0.0367(2) 0.00238(18) 0.00483(14) 0.00499(15) O2B 0.024(3) 0.024(3) 0.034(3) 0.020(2) -0.003(3) -0.006(2) C9 0.0195(14) 0.0263(18) 0.0278(17) 0.0030(14) -0.0003(13) -0.0033(13) O3B 0.026(4) 0.035(3) 0.034(3) 0.0219(19) 0.002(3) 0.009(3) C8 0.0177(14) 0.0234(17) 0.0260(16) 0.0062(14) 0.0010(12) -0.0011(12) C15 0.0348(17) 0.0201(17) 0.0253(16) 0.0102(14) 0.0092(14) 0.0070(13) C19 0.0270(16) 0.0313(19) 0.0359(19) 0.0193(16) 0.0101(14) 0.0068(14) C18 0.0311(17) 0.0231(17) 0.0242(16) 0.0105(14) 0.0092(13) 0.0078(13) C10 0.0244(16) 0.0310(19) 0.0259(17) 0.0007(15) 0.0022(13) -0.0004(14) C12 0.0199(15) 0.0321(19) 0.0308(18) 0.0072(15) -0.0020(13) -0.0037(13) C13 0.0233(15) 0.0274(18) 0.0273(17) 0.0026(14) -0.0016(13) -0.0044(13) C20 0.0258(16) 0.0298(19) 0.0352(19) 0.0177(16) 0.0037(14) 0.0054(14) C11 0.0202(15) 0.0304(19) 0.0297(17) 0.0081(15) 0.0036(13) 0.0027(13) C16 0.0340(18) 0.0244(18) 0.0322(18) 0.0092(15) 0.0066(15) -0.0034(14) O1 0.0165(10) 0.0250(12) 0.0266(12) 0.0002(10) 0.0006(9) -0.0009(9) C2 0.0244(15) 0.0159(16) 0.0279(17) 0.0039(13) -0.0004(13) 0.0008(12) C1 0.0192(14) 0.0204(16) 0.0221(15) 0.0015(13) 0.0000(12) 0.0001(12) C28 0.0242(16) 0.0181(17) 0.040(2) 0.0098(15) 0.0019(14) 0.0048(13) C7 0.0171(14) 0.0280(18) 0.0255(16) 0.0029(14) 0.0006(12) -0.0026(12) C32 0.0273(16) 0.0324(19) 0.0251(16) 0.0147(15) 0.0033(13) -0.0003(14) C6 0.0263(15) 0.0239(17) 0.0186(15) 0.0080(13) 0.0009(12) -0.0004(13) C33 0.0377(19) 0.055(3) 0.0207(17) 0.0133(17) 0.0016(15) 0.0068(17) C3B 0.016(3) 0.021(3) 0.022(3) 0.010(2) -0.006(2) -0.003(2) C29 0.0332(18) 0.0171(18) 0.053(2) 0.0048(16) 0.0058(17) 0.0016(14) C5B 0.014(3) 0.020(3) 0.023(3) 0.010(2) -0.005(2) -0.001(2) C14B 0.017(3) 0.022(3) 0.030(4) 0.010(2) -0.010(3) -0.006(2) C4A 0.030(7) 0.029(7) 0.035(7) 0.007(5) 0.011(6) 0.004(5) C17 0.0299(17) 0.0309(19) 0.0301(18) 0.0095(15) 0.0019(14) 0.0003(14) Br3B 0.0358(5) 0.0829(12) 0.214(2) 0.1202(15) -0.0377(10) -0.0161(6) Br3A 0.0343(9) 0.0379(10) 0.0721(14) 0.0381(11) -0.0105(9) 0.0017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br2 C18 1.907(3) . ? Br1 C11 1.901(3) . ? O2B C15 1.391(7) . ? O2B C14B 1.470(9) . ? C9 H9 0.9500 . ? C9 C8 1.388(4) . ? C9 C10 1.394(4) . ? O3B C21B 1.430(10) . ? O3B C22B 1.304(11) . ? C8 C13 1.400(4) . ? C8 O1 1.369(4) . ? C15 C20 1.386(5) . ? C15 C16 1.402(5) . ? C15 O2A 1.34(2) . ? C19 H19 0.9500 . ? C19 C18 1.390(5) . ? C19 C20 1.380(5) . ? C18 C17 1.392(5) . ? C10 H10 0.9500 . ? C10 C11 1.383(4) . ? C12 H12 0.9500 . ? C12 C13 1.371(4) . ? C12 C11 1.389(5) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C16 H16 0.9500 . ? C16 C17 1.380(5) . ? O1 C7 1.449(3) . ? C2 C1 1.390(5) . ? C2 C28 1.523(4) . ? C2 C3B 1.450(7) . ? C2 C3A 1.366(17) . ? C1 C7 1.506(4) . ? C1 C6 1.412(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.534(5) . ? C21B H21A 0.9900 . ? C21B H21B 0.9900 . ? C21B C5B 1.499(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.520(4) . ? C32 C33 1.536(5) . ? C6 C5B 1.451(7) . ? C6 C5A 1.336(17) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.501(9) . ? C3B C4B 1.391(8) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.408(8) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C4A C30A 1.502(14) . ? C4A C5A 1.39(2) . ? C4A C3A 1.43(2) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.451(14) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.537(6) . ? C30B C4B 1.509(7) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C22B C23B 1.383(7) . ? C22B C27B 1.403(7) . ? Br3B C25B 1.898(6) . ? Br3A C25A 1.858(12) . ? C27A H27A 0.9500 . ? C27A C26A 1.381(12) . ? C27A C22A 1.364(12) . ? C23A H23A 0.9500 . ? C23A C24A 1.403(12) . ? C23A C22A 1.414(12) . ? C24B H24B 0.9500 . ? C24B C25B 1.387(7) . ? C24B C23B 1.390(7) . ? C25A C26A 1.367(12) . ? C25A C24A 1.350(12) . ? C26A H26A 0.9500 . ? C25B C26B 1.371(7) . ? C26B H26B 0.9500 . ? C26B C27B 1.386(7) . ? C24A H24A 0.9500 . ? C23B H23B 0.9500 . ? C27B H27B 0.9500 . ? C5A C21A 1.50(2) . ? C3A C14A 1.51(2) . ? C21A H21C 0.9900 . ? C21A H21D 0.9900 . ? C21A O3A 1.49(2) . ? O3A C22A 1.57(3) . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? C14A O2A 1.412(17) . ? 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 C15 O2B C14B 119.9(5) . . ? C8 C9 H9 120.4 . . ? C8 C9 C10 119.2(3) . . ? C10 C9 H9 120.4 . . ? C22B O3B C21B 118.6(7) . . ? C9 C8 C13 120.1(3) . . ? O1 C8 C9 124.3(3) . . ? O1 C8 C13 115.6(3) . . ? O2B C15 C16 119.4(4) . . ? C20 C15 O2B 120.7(4) . . ? C20 C15 C16 119.9(3) . . ? O2A C15 O2B 13.7(8) . . ? O2A C15 C20 134.4(7) . . ? O2A C15 C16 105.7(7) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C20 C19 C18 119.3(3) . . ? C19 C18 Br2 118.9(2) . . ? C19 C18 C17 121.1(3) . . ? C17 C18 Br2 120.0(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C13 C12 H12 120.5 . . ? C13 C12 C11 119.0(3) . . ? C11 C12 H12 120.5 . . ? C8 C13 H13 119.7 . . ? C12 C13 C8 120.7(3) . . ? C12 C13 H13 119.7 . . ? C15 C20 H20 119.8 . . ? C19 C20 C15 120.4(3) . . ? C19 C20 H20 119.8 . . ? C10 C11 Br1 119.3(2) . . ? C10 C11 C12 121.2(3) . . ? C12 C11 Br1 119.5(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 120.0 . . ? C8 O1 C7 118.8(2) . . ? C1 C2 C28 121.3(3) . . ? C1 C2 C3B 118.9(3) . . ? C3B C2 C28 119.6(4) . . ? C3A C2 C1 119.8(8) . . ? C3A C2 C28 117.8(8) . . ? C3A C2 C3B 15.9(6) . . ? C2 C1 C7 118.8(3) . . ? C2 C1 C6 120.9(3) . . ? C6 C1 C7 120.1(3) . . ? C2 C28 H28A 109.2 . . ? C2 C28 H28B 109.2 . . ? C2 C28 C29 112.2(3) . . ? H28A C28 H28B 107.9 . . ? C29 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? O3B C21B H21A 109.5 . . ? O3B C21B H21B 109.5 . . ? O3B C21B C5B 110.6(6) . . ? H21A C21B H21B 108.1 . . ? C5B C21B H21A 109.5 . . ? C5B C21B H21B 109.5 . . ? O1 C7 C1 105.5(2) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 108.0 . . ? C6 C32 H32A 109.4 . . ? C6 C32 H32B 109.4 . . ? C6 C32 C33 111.4(3) . . ? C33 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C1 C6 C32 121.1(3) . . ? C1 C6 C5B 118.8(3) . . ? C5B C6 C32 119.6(3) . . ? C5A C6 C1 118.8(8) . . ? C5A C6 C32 119.2(8) . . ? C5A C6 C5B 16.0(6) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 118.6(5) . . ? C4B C3B C2 120.8(5) . . ? C4B C3B C14B 120.0(6) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 120.0(5) . . ? C4B C5B C21B 119.4(5) . . ? C4B C5B C6 120.1(5) . . ? O2B C14B C3B 106.0(6) . . ? O2B C14B H14A 110.5 . . ? O2B C14B H14B 110.5 . . ? C3B C14B H14A 110.5 . . ? C3B C14B H14B 110.5 . . ? H14A C14B H14B 108.7 . . ? C5A C4A C30A 122.9(11) . . ? C5A C4A C3A 120.2(12) . . ? C3A C4A C30A 116.9(11) . . ? C4A C30A H30A 109.7 . . ? C4A C30A H30B 109.7 . . ? H30A C30A H30B 108.2 . . ? C31A C30A C4A 109.9(10) . . ? C31A C30A H30A 109.7 . . ? C31A C30A H30B 109.7 . . ? H30C C30B H30D 107.3 . . ? C31B C30B H30C 108.2 . . ? C31B C30B H30D 108.2 . . ? C4B C30B H30C 108.2 . . ? C4B C30B H30D 108.2 . . ? C4B C30B C31B 116.4(4) . . ? C18 C17 H17 120.4 . . ? C16 C17 C18 119.2(3) . . ? C16 C17 H17 120.4 . . ? C3B C4B C5B 119.6(5) . . ? C3B C4B C30B 120.5(5) . . ? C5B C4B C30B 119.8(5) . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? O3B C22B C23B 117.3(6) . . ? O3B C22B C27B 123.0(6) . . ? C23B C22B C27B 119.5(5) . . ? C26A C27A H27A 120.2 . . ? C22A C27A H27A 120.2 . . ? C22A C27A C26A 119.5(11) . . ? C24A C23A H23A 120.6 . . ? C24A C23A C22A 118.9(11) . . ? C22A C23A H23A 120.6 . . ? C25B C24B H24B 119.6 . . ? C25B C24B C23B 120.7(5) . . ? C23B C24B H24B 119.6 . . ? C26A C25A Br3A 123.2(8) . . ? C24A C25A Br3A 114.6(8) . . ? C24A C25A C26A 122.0(11) . . ? C27A C26A H26A 119.9 . . ? C25A C26A C27A 120.2(11) . . ? C25A C26A H26A 119.9 . . ? C24B C25B Br3B 118.1(4) . . ? C26B C25B Br3B 121.6(4) . . ? C26B C25B C24B 120.2(5) . . ? C25B C26B H26B 120.2 . . ? C25B C26B C27B 119.7(5) . . ? C27B C26B H26B 120.2 . . ? C23A C24A H24A 120.7 . . ? C25A C24A C23A 118.7(11) . . ? C25A C24A H24A 120.7 . . ? C22B C23B C24B 119.3(5) . . ? C22B C23B H23B 120.3 . . ? C24B C23B H23B 120.3 . . ? C22B C27B H27B 119.8 . . ? C26B C27B C22B 120.4(5) . . ? C26B C27B H27B 119.8 . . ? C6 C5A C4A 120.8(13) . . ? C6 C5A C21A 119.4(13) . . ? C4A C5A C21A 119.8(13) . . ? C2 C3A C4A 118.5(13) . . ? C2 C3A C14A 121.2(13) . . ? C4A C3A C14A 120.2(13) . . ? C5A C21A H21C 109.7 . . ? C5A C21A H21D 109.7 . . ? H21C C21A H21D 108.2 . . ? O3A C21A C5A 109.9(13) . . ? O3A C21A H21C 109.7 . . ? O3A C21A H21D 109.7 . . ? C21A O3A C22A 110.1(14) . . ? C27A C22A C23A 120.1(11) . . ? C27A C22A O3A 127.5(12) . . ? C23A C22A O3A 112.3(11) . . ? C3A C14A H14C 110.4 . . ? C3A C14A H14D 110.4 . . ? H14C C14A H14D 108.6 . . ? O2A C14A C3A 106.7(14) . . ? O2A C14A H14C 110.4 . . ? O2A C14A H14D 110.4 . . ? C15 O2A C14A 108.0(14) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 178.6(2) . . . . ? O2B C15 C20 C19 179.5(4) . . . . ? O2B C15 C16 C17 -179.1(4) . . . . ? O2B C15 O2A C14A -14(3) . . . . ? C9 C8 C13 C12 -1.0(5) . . . . ? C9 C8 O1 C7 -0.2(5) . . . . ? C9 C10 C11 Br1 178.7(3) . . . . ? C9 C10 C11 C12 0.0(6) . . . . ? O3B C21B C5B C6 78.5(7) . . . . ? O3B C21B C5B C4B -109.7(7) . . . . ? O3B C22B C23B C24B 173.3(6) . . . . ? O3B C22B C27B C26B -173.5(7) . . . . ? C8 C9 C10 C11 -1.0(5) . . . . ? C8 O1 C7 C1 174.5(3) . . . . ? C15 O2B C14B C3B -170.7(6) . . . . ? C15 C16 C17 C18 -0.7(5) . . . . ? C19 C18 C17 C16 -0.4(5) . . . . ? C18 C19 C20 C15 -0.1(5) . . . . ? C10 C9 C8 C13 1.5(5) . . . . ? C10 C9 C8 O1 -178.2(3) . . . . ? C13 C8 O1 C7 -179.9(3) . . . . ? C13 C12 C11 Br1 -178.2(3) . . . . ? C13 C12 C11 C10 0.5(5) . . . . ? C20 C15 C16 C17 1.3(5) . . . . ? C20 C15 O2A C14A -9(2) . . . . ? C20 C19 C18 Br2 -178.2(2) . . . . ? C20 C19 C18 C17 0.8(5) . . . . ? C11 C12 C13 C8 0.0(5) . . . . ? C16 C15 C20 C19 -0.9(5) . . . . ? C16 C15 O2A C14A 170.3(11) . . . . ? O1 C8 C13 C12 178.7(3) . . . . ? C2 C1 C7 O1 -83.9(3) . . . . ? C2 C1 C6 C32 -178.2(3) . . . . ? C2 C1 C6 C5B -6.2(5) . . . . ? C2 C1 C6 C5A 12.2(8) . . . . ? C2 C3B C14B O2B 77.0(7) . . . . ? C2 C3B C4B C5B -1.8(9) . . . . ? C2 C3B C4B C30B 174.2(5) . . . . ? C2 C3A C14A O2A 92.7(16) . . . . ? C1 C2 C28 C29 -93.1(4) . . . . ? C1 C2 C3B C14B -178.5(5) . . . . ? C1 C2 C3B C4B -6.6(7) . . . . ? C1 C2 C3A C4A 0.3(14) . . . . ? C1 C2 C3A C14A -179.0(9) . . . . ? C1 C6 C5B C21B 169.2(4) . . . . ? C1 C6 C5B C4B -2.5(7) . . . . ? C1 C6 C5A C4A -9.0(15) . . . . ? C1 C6 C5A C21A 171.3(8) . . . . ? C28 C2 C1 C7 -0.2(4) . . . . ? C28 C2 C1 C6 -175.3(3) . . . . ? C28 C2 C3B C14B 7.4(7) . . . . ? C28 C2 C3B C4B 179.2(4) . . . . ? C28 C2 C3A C4A 168.4(9) . . . . ? C28 C2 C3A C14A -10.9(14) . . . . ? C21B O3B C22B C23B 166.9(6) . . . . ? C21B O3B C22B C27B -17.6(11) . . . . ? C21B C5B C4B C3B -165.4(5) . . . . ? C21B C5B C4B C30B 18.5(8) . . . . ? C7 C1 C6 C32 6.7(4) . . . . ? C7 C1 C6 C5B 178.8(4) . . . . ? C7 C1 C6 C5A -162.9(7) . . . . ? C32 C6 C5B C21B -18.6(7) . . . . ? C32 C6 C5B C4B 169.7(5) . . . . ? C32 C6 C5A C4A -178.8(10) . . . . ? C32 C6 C5A C21A 1.5(14) . . . . ? C6 C1 C7 O1 91.3(3) . . . . ? C6 C5B C4B C3B 6.3(9) . . . . ? C6 C5B C4B C30B -169.7(5) . . . . ? C6 C5A C21A O3A 63.7(16) . . . . ? C33 C32 C6 C1 87.0(4) . . . . ? C33 C32 C6 C5B -85.0(5) . . . . ? C33 C32 C6 C5A -103.4(7) . . . . ? C3B C2 C1 C7 -174.3(4) . . . . ? C3B C2 C1 C6 10.6(5) . . . . ? C3B C2 C28 C29 80.9(5) . . . . ? C3B C2 C3A C4A -91(3) . . . . ? C3B C2 C3A C14A 90(3) . . . . ? C5B C6 C5A C4A 85(3) . . . . ? C5B C6 C5A C21A -94(3) . . . . ? C14B O2B C15 C20 -13.8(8) . . . . ? C14B O2B C15 C16 166.7(5) . . . . ? C14B O2B C15 O2A 162(5) . . . . ? C14B C3B C4B C5B 169.9(6) . . . . ? C14B C3B C4B C30B -14.1(9) . . . . ? C4A C5A C21A O3A -115.9(16) . . . . ? C4A C3A C14A O2A -86.5(17) . . . . ? C30A C4A C5A C6 -175.8(11) . . . . ? C30A C4A C5A C21A 4(2) . . . . ? C30A C4A C3A C2 -179.6(10) . . . . ? C30A C4A C3A C14A -0.3(19) . . . . ? C31B C30B C4B C3B 83.9(6) . . . . ? C31B C30B C4B C5B -100.0(6) . . . . ? C4B C3B C14B O2B -94.9(7) . . . . ? C22B O3B C21B C5B -168.5(7) . . . . ? Br3B C25B C26B C27B -177.9(4) . . . . ? Br3A C25A C26A C27A -178.9(10) . . . . ? Br3A C25A C24A C23A -177.6(9) . . . . ? C24B C25B C26B C27B -0.3(8) . . . . ? C26A C27A C22A C23A -3.6(19) . . . . ? C26A C27A C22A O3A 174.3(14) . . . . ? C26A C25A C24A C23A 7.8(19) . . . . ? C25B C24B C23B C22B 1.6(8) . . . . ? C25B C26B C27B C22B -0.5(8) . . . . ? C24A C23A C22A C27A 6.6(19) . . . . ? C24A C23A C22A O3A -171.6(12) . . . . ? C24A C25A C26A C27A -4.8(19) . . . . ? C23B C22B C27B C26B 1.9(8) . . . . ? C23B C24B C25B Br3B 177.5(4) . . . . ? C23B C24B C25B C26B -0.2(8) . . . . ? C27B C22B C23B C24B -2.4(8) . . . . ? C5A C6 C5B C21B 75(3) . . . . ? C5A C6 C5B C4B -97(3) . . . . ? C5A C4A C30A C31A 80.7(15) . . . . ? C5A C4A C3A C2 2.8(19) . . . . ? C5A C4A C3A C14A -178.0(13) . . . . ? C5A C21A O3A C22A 172.4(12) . . . . ? C3A C2 C1 C7 167.5(7) . . . . ? C3A C2 C1 C6 -7.7(8) . . . . ? C3A C2 C28 C29 99.0(7) . . . . ? C3A C2 C3B C14B -81(3) . . . . ? C3A C2 C3B C4B 91(3) . . . . ? C3A C4A C30A C31A -96.9(13) . . . . ? C3A C4A C5A C6 2(2) . . . . ? C3A C4A C5A C21A -178.6(12) . . . . ? C3A C14A O2A C15 -173.8(12) . . . . ? C21A O3A C22A C27A -12(2) . . . . ? C21A O3A C22A C23A 165.8(13) . . . . ? C22A C27A C26A C25A 2.5(19) . . . . ? C22A C23A C24A C25A -8.6(19) . . . . ? O2A C15 C20 C19 178.2(12) . . . . ? O2A C15 C16 C17 -178.0(9) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.029 0.500 0.000 361 43 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962429' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-ea-154K _audit_creation_date 2013-12-23 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-ea, 154 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Br3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Br3 O5' _chemical_formula_weight 805.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.6832(5) _cell_length_b 13.3456(7) _cell_length_c 14.8992(9) _cell_angle_alpha 111.677(6) _cell_angle_beta 92.868(5) _cell_angle_gamma 90.530(4) _cell_volume 1786.18(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4919 _cell_measurement_temperature 154(2) _cell_measurement_theta_max 29.1134 _cell_measurement_theta_min 3.7194 _exptl_absorpt_coefficient_mu 3.428 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_unetI/netI 0.0593 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 23767 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.18 _diffrn_reflns_theta_min 4.06 _diffrn_ambient_temperature 154(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.868 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0462306000 _diffrn_orient_matrix_UB_12 0.0453565000 _diffrn_orient_matrix_UB_13 0.0193816000 _diffrn_orient_matrix_UB_21 0.0095891000 _diffrn_orient_matrix_UB_22 -0.0102013000 _diffrn_orient_matrix_UB_23 0.0433306000 _diffrn_orient_matrix_UB_31 0.0561670000 _diffrn_orient_matrix_UB_32 -0.0333573000 _diffrn_orient_matrix_UB_33 -0.0194939000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5728 _reflns_number_total 8389 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.868 _refine_diff_density_min -0.844 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 393 _refine_ls_number_reflns 8389 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0450 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1104 _refine_ls_wR_factor_ref 0.1215 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uiso(C25B) = Uiso(C25A) Uiso(C26B) = Uiso(C26A) Uiso(C24B) = Uiso(C24A) 4. Others Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(Br3A)=Sof(C27A)=Sof(H27A)=Sof(C23A)=Sof(H23A)=Sof(C25A)= Sof(C26A)=Sof(H26A)=Sof(C24A)=Sof(H24A)=Sof(C5A)=Sof(C3A)=Sof(C21A)=Sof(H21C)= Sof(H21D)=Sof(O3A)=Sof(C22A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(O2A)=1-FVAR(1) Sof(O2B)=Sof(O3B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C22B)=Sof(Br3B)=Sof(C24B)=Sof(H24B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C23B)=Sof(H23B)=Sof(C27B)=Sof(H27B)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 5.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C16(H16), C17(H17), C27A(H27A), C23A(H23A), C24B(H24B), C26A(H26A), C26B(H26B), C24A(H24A), C23B(H23B), C27B(H27B) 5.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.98562(4) 0.12063(3) 0.97046(2) 0.04201(12) Uani 1 1 d . . . Br1 Br 1.72274(3) 0.03734(3) 0.12670(3) 0.04243(12) Uani 1 1 d . . . O2B O 0.9194(8) 0.2802(6) 0.6387(5) 0.0311(15) Uani 0.641(8) 1 d A 1 . C9 C 1.3100(3) 0.1080(3) 0.1781(2) 0.0290(7) Uani 1 1 d . . . H9 H 1.2224 0.0819 0.1456 0.035 Uiso 1 1 calc . . R O3B O 0.6876(8) 0.5358(7) 0.3631(6) 0.0334(16) Uani 0.641(8) 1 d A 1 . C8 C 1.3185(3) 0.1913(2) 0.2674(2) 0.0259(7) Uani 1 1 d . . . C15 C 0.9360(3) 0.2463(2) 0.7178(2) 0.0301(7) Uani 1 1 d . . . C19 C 0.8430(3) 0.1540(3) 0.8130(2) 0.0340(8) Uani 1 1 d . . . H19 H 0.7689 0.1156 0.8267 0.041 Uiso 1 1 calc A . R C18 C 0.9652(3) 0.1743(3) 0.8686(2) 0.0295(7) Uani 1 1 d A . . C10 C 1.4315(3) 0.0625(3) 0.1361(2) 0.0311(7) Uani 1 1 d . . . H10 H 1.4271 0.0044 0.0752 0.037 Uiso 1 1 calc . . R C12 C 1.5671(3) 0.1867(3) 0.2726(2) 0.0338(8) Uani 1 1 d . . . H12 H 1.6546 0.2138 0.3047 0.041 Uiso 1 1 calc . . R C13 C 1.4469(3) 0.2301(3) 0.3135(2) 0.0318(7) Uani 1 1 d . . . H13 H 1.4517 0.2880 0.3745 0.038 Uiso 1 1 calc . . R C20 C 0.8283(3) 0.1899(3) 0.7366(2) 0.0333(8) Uani 1 1 d A . . H20 H 0.7444 0.1756 0.6975 0.040 Uiso 1 1 calc . . R C11 C 1.5577(3) 0.1022(3) 0.1833(2) 0.0300(7) Uani 1 1 d . . . C16 C 1.0579(4) 0.2682(3) 0.7754(2) 0.0368(8) Uani 1 1 d A . . H16 H 1.1308 0.3086 0.7631 0.044 Uiso 1 1 calc . . R O1 O 1.2064(2) 0.24040(17) 0.31663(15) 0.0303(5) Uani 1 1 d A . . C2 C 0.9404(3) 0.2264(2) 0.4207(2) 0.0263(7) Uani 1 1 d . . . C1 C 0.9708(3) 0.2651(2) 0.3484(2) 0.0245(6) Uani 1 1 d A . . C28 C 1.0019(3) 0.1241(2) 0.4240(2) 0.0306(7) Uani 1 1 d A . . H28A H 1.0176 0.1314 0.4923 0.037 Uiso 1 1 calc . . R H28B H 1.0928 0.1141 0.3947 0.037 Uiso 1 1 calc . . R C21B C 0.7863(7) 0.5332(5) 0.4360(4) 0.0264(15) Uiso 0.641(8) 1 d A 1 . H21A H 0.7479 0.5676 0.5003 0.032 Uiso 0.641(8) 1 calc A 1 R H21B H 0.8707 0.5750 0.4346 0.032 Uiso 0.641(8) 1 calc A 1 R C7 C 1.0692(3) 0.2034(3) 0.2730(2) 0.0271(7) Uani 1 1 d . . . H7A H 1.0569 0.1248 0.2566 0.033 Uiso 1 1 calc A . R H7B H 1.0533 0.2189 0.2133 0.033 Uiso 1 1 calc . . R C32 C 0.9499(3) 0.4037(3) 0.2686(2) 0.0317(7) Uani 1 1 d A . . H32A H 1.0423 0.3801 0.2448 0.038 Uiso 1 1 calc . . R H32B H 0.9511 0.4836 0.2942 0.038 Uiso 1 1 calc . . R C6 C 0.9208(3) 0.3642(3) 0.3498(2) 0.0272(7) Uani 1 1 d . . . C33 C 0.8411(4) 0.3605(3) 0.1845(3) 0.0435(9) Uani 1 1 d . . . H33A H 0.8625 0.3881 0.1341 0.065 Uiso 1 1 calc A . GR H33B H 0.7495 0.3842 0.2077 0.065 Uiso 1 1 calc . . GR H33C H 0.8415 0.2815 0.1577 0.065 Uiso 1 1 calc . . GR C3B C 0.8354(7) 0.2791(5) 0.4872(4) 0.0197(13) Uani 0.641(8) 1 d A 1 . C29 C 0.9093(4) 0.0245(3) 0.3706(3) 0.0383(8) Uani 1 1 d . . . H29A H 0.9025 0.0118 0.3013 0.057 Uiso 1 1 calc A . GR H29B H 0.8168 0.0362 0.3959 0.057 Uiso 1 1 calc . . GR H29C H 0.9490 -0.0383 0.3802 0.057 Uiso 1 1 calc . . GR C5B C 0.8235(7) 0.4206(5) 0.4217(4) 0.0202(13) Uani 0.641(8) 1 d A 1 . C14B C 0.8048(8) 0.2396(6) 0.5672(5) 0.0287(19) Uani 0.641(8) 1 d A 1 . H14A H 0.7163 0.2679 0.5956 0.034 Uiso 0.641(8) 1 calc A 1 R H14B H 0.7990 0.1598 0.5423 0.034 Uiso 0.641(8) 1 calc A 1 R C4A C 0.8383(13) 0.3967(9) 0.5042(8) 0.026(2) Uani 0.359(8) 1 d A 2 . C30A C 0.7665(10) 0.4676(8) 0.5944(7) 0.037(3) Uiso 0.359(8) 1 d A 2 . H30A H 0.7883 0.4439 0.6489 0.044 Uiso 0.359(8) 1 calc A 2 R H30B H 0.7976 0.5439 0.6137 0.044 Uiso 0.359(8) 1 calc A 2 R C30B C 0.6613(6) 0.4224(4) 0.5497(4) 0.0268(13) Uani 0.641(8) 1 d A 1 . H30C H 0.6000 0.3632 0.5509 0.032 Uiso 0.641(8) 1 calc A 1 R H30D H 0.6063 0.4650 0.5194 0.032 Uiso 0.641(8) 1 calc A 1 R C31B C 0.7010(5) 0.4958(4) 0.6549(3) 0.0278(14) Uani 0.641(8) 1 d A 1 . H31A H 0.7568 0.5577 0.6557 0.042 Uiso 0.641(8) 1 calc A 1 GR H31B H 0.7546 0.4551 0.6868 0.042 Uiso 0.641(8) 1 calc A 1 GR H31C H 0.6169 0.5213 0.6894 0.042 Uiso 0.641(8) 1 calc A 1 GR C17 C 1.0739(4) 0.2313(3) 0.8506(2) 0.0363(8) Uani 1 1 d . . . H17 H 1.1580 0.2449 0.8893 0.044 Uiso 1 1 calc A . R C4B C 0.7761(6) 0.3733(5) 0.4860(4) 0.0174(12) Uani 0.641(8) 1 d A 1 . C31A C 0.6183(14) 0.4556(12) 0.5686(11) 0.050(4) Uiso 0.359(8) 1 d A 2 . H31D H 0.5997 0.4709 0.5097 0.075 Uiso 0.359(8) 1 calc A 2 GR H31E H 0.5687 0.5062 0.6215 0.075 Uiso 0.359(8) 1 calc A 2 GR H31F H 0.5870 0.3816 0.5571 0.075 Uiso 0.359(8) 1 calc A 2 GR C22B C 0.6626(8) 0.6291(6) 0.3561(6) 0.028(2) Uiso 0.641(8) 1 d A 1 . Br3B Br 0.5218(6) 0.9507(4) 0.3275(4) 0.0884(12) Uani 0.641(8) 1 d A 1 . Br3A Br 0.5099(10) 0.9624(7) 0.3489(6) 0.0560(10) Uani 0.359(8) 1 d A 2 . C27A C 0.6928(12) 0.7399(8) 0.4497(9) 0.021(3) Uiso 0.359(8) 1 d A 2 . H27A H 0.7432 0.7385 0.5055 0.025 Uiso 0.359(8) 1 calc A 2 R C23A C 0.5858(12) 0.6468(10) 0.2915(9) 0.025(3) Uiso 0.359(8) 1 d A 2 . H23A H 0.5596 0.5812 0.2397 0.030 Uiso 0.359(8) 1 calc A 2 R C24B C 0.5440(6) 0.7198(5) 0.2638(5) 0.0322(10) Uiso 0.641(8) 1 d A 1 . H24B H 0.4897 0.7172 0.2080 0.039 Uiso 0.641(8) 1 calc A 1 R C25A C 0.5722(10) 0.8400(8) 0.3692(8) 0.0274(10) Uiso 0.359(8) 1 d A 2 . C26A C 0.6472(10) 0.8364(9) 0.4477(8) 0.0301(11) Uiso 0.359(8) 1 d A 2 . H26A H 0.6683 0.9012 0.5016 0.036 Uiso 0.359(8) 1 calc A 2 R C25B C 0.5782(5) 0.8182(5) 0.3375(4) 0.0274(10) Uiso 0.641(8) 1 d A 1 . C26B C 0.6551(6) 0.8237(5) 0.4189(4) 0.0301(11) Uiso 0.641(8) 1 d A 1 . H26B H 0.6787 0.8917 0.4682 0.036 Uiso 0.641(8) 1 calc A 1 R C24A C 0.5451(11) 0.7476(8) 0.2895(8) 0.0322(10) Uiso 0.359(8) 1 d A 2 . H24A H 0.4991 0.7512 0.2330 0.039 Uiso 0.359(8) 1 calc A 2 R C23B C 0.5901(8) 0.6246(7) 0.2724(6) 0.037(2) Uiso 0.641(8) 1 d A 1 . H23B H 0.5716 0.5572 0.2210 0.044 Uiso 0.641(8) 1 calc A 1 R C27B C 0.6988(8) 0.7287(5) 0.4291(6) 0.033(2) Uiso 0.641(8) 1 d A 1 . H27B H 0.7526 0.7318 0.4852 0.039 Uiso 0.641(8) 1 calc A 1 R C5A C 0.8680(12) 0.4320(11) 0.4310(10) 0.024(4) Uiso 0.359(8) 1 d A 2 . C3A C 0.8776(12) 0.2925(11) 0.4985(9) 0.021(3) Uiso 0.359(8) 1 d A 2 . C21A C 0.8293(12) 0.5446(8) 0.4392(7) 0.023(2) Uiso 0.359(8) 1 d A 2 . H21C H 0.7950 0.5845 0.5039 0.028 Uiso 0.359(8) 1 calc A 2 R H21D H 0.9116 0.5843 0.4311 0.028 Uiso 0.359(8) 1 calc A 2 R O3A O 0.7201(14) 0.5366(14) 0.3632(12) 0.025(3) Uiso 0.359(8) 1 d A 2 . C22A C 0.6666(14) 0.6472(11) 0.3730(9) 0.027(4) Uiso 0.359(8) 1 d A 2 . C14A C 0.8419(13) 0.2522(12) 0.5788(11) 0.016(3) Uiso 0.359(8) 1 d A 2 . H14C H 0.7524 0.2807 0.6053 0.020 Uiso 0.359(8) 1 calc A 2 R H14D H 0.8352 0.1724 0.5534 0.020 Uiso 0.359(8) 1 calc A 2 R O2A O 0.9513(13) 0.2907(12) 0.6520(11) 0.027(3) Uiso 0.359(8) 1 d A 2 . 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 Br2 0.0507(2) 0.0529(3) 0.0304(2) 0.02379(18) 0.00805(16) 0.01232(17) Br1 0.02656(18) 0.0588(3) 0.0379(2) 0.01259(18) 0.00493(14) 0.00800(16) O2B 0.038(4) 0.035(3) 0.030(3) 0.025(2) -0.008(3) -0.012(3) C9 0.0234(15) 0.0358(19) 0.0278(17) 0.0119(15) -0.0001(12) 0.0010(13) O3B 0.029(4) 0.031(3) 0.045(3) 0.020(2) -0.003(3) 0.008(3) C8 0.0246(15) 0.0251(17) 0.0282(17) 0.0098(14) 0.0025(12) 0.0008(12) C15 0.0399(18) 0.0242(17) 0.0309(18) 0.0142(14) 0.0127(14) 0.0073(14) C19 0.0346(18) 0.038(2) 0.0394(19) 0.0249(16) 0.0095(15) 0.0076(15) C18 0.0368(18) 0.0288(18) 0.0259(17) 0.0126(14) 0.0069(13) 0.0089(14) C10 0.0314(17) 0.0357(19) 0.0227(16) 0.0068(14) 0.0003(13) 0.0015(14) C12 0.0287(17) 0.037(2) 0.0343(19) 0.0116(16) -0.0034(14) -0.0025(14) C13 0.0290(16) 0.0320(19) 0.0289(18) 0.0058(15) -0.0040(13) -0.0030(14) C20 0.0326(17) 0.037(2) 0.0370(19) 0.0210(16) 0.0029(14) 0.0054(14) C11 0.0253(15) 0.040(2) 0.0293(17) 0.0177(15) 0.0009(13) 0.0039(14) C16 0.043(2) 0.032(2) 0.037(2) 0.0151(16) 0.0095(16) -0.0032(15) O1 0.0229(11) 0.0299(12) 0.0296(12) 0.0014(10) -0.0005(9) -0.0001(9) C2 0.0308(16) 0.0185(16) 0.0291(17) 0.0083(13) -0.0008(13) 0.0039(12) C1 0.0243(15) 0.0254(17) 0.0229(16) 0.0080(13) -0.0012(12) 0.0012(12) C28 0.0293(16) 0.0243(17) 0.0397(19) 0.0135(15) 0.0011(14) 0.0064(13) C7 0.0237(15) 0.0285(18) 0.0271(17) 0.0082(14) -0.0020(12) -0.0005(13) C32 0.0351(18) 0.0343(19) 0.0316(18) 0.0187(15) 0.0054(14) 0.0016(14) C6 0.0293(16) 0.0284(18) 0.0259(16) 0.0128(14) -0.0003(13) 0.0000(13) C33 0.047(2) 0.054(2) 0.0310(19) 0.0185(18) 0.0011(16) 0.0097(18) C3B 0.015(3) 0.021(3) 0.024(3) 0.009(2) -0.002(2) -0.004(2) C29 0.0395(19) 0.0224(18) 0.051(2) 0.0117(16) 0.0007(16) 0.0007(14) C5B 0.018(3) 0.020(3) 0.023(3) 0.008(2) -0.002(2) 0.000(2) C14B 0.021(3) 0.033(4) 0.037(4) 0.019(3) -0.013(3) -0.006(3) C4A 0.023(6) 0.025(6) 0.028(6) 0.007(4) 0.004(5) 0.001(5) C30B 0.024(3) 0.021(3) 0.035(3) 0.010(2) 0.005(2) 0.008(2) C31B 0.032(3) 0.027(3) 0.021(3) 0.005(2) 0.008(2) 0.002(2) C17 0.0370(19) 0.039(2) 0.0323(19) 0.0127(16) 0.0031(15) 0.0016(15) C4B 0.009(2) 0.020(3) 0.023(3) 0.008(2) -0.004(2) -0.002(2) Br3B 0.0417(10) 0.076(2) 0.191(4) 0.105(2) -0.0286(19) -0.0086(14) Br3A 0.0401(17) 0.0389(13) 0.1010(17) 0.0425(13) -0.0161(11) 0.0041(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br2 C18 1.905(3) . ? Br1 C11 1.906(3) . ? O2B C15 1.412(7) . ? O2B C14B 1.451(9) . ? C9 H9 0.9500 . ? C9 C8 1.381(4) . ? C9 C10 1.397(4) . ? O3B C21B 1.422(10) . ? O3B C22B 1.311(12) . ? C8 C13 1.387(4) . ? C8 O1 1.372(3) . ? C15 C20 1.381(4) . ? C15 C16 1.386(5) . ? C15 O2A 1.332(16) . ? C19 H19 0.9500 . ? C19 C18 1.375(5) . ? C19 C20 1.390(4) . ? C18 C17 1.387(5) . ? C10 H10 0.9500 . ? C10 C11 1.377(4) . ? C12 H12 0.9500 . ? C12 C13 1.372(4) . ? C12 C11 1.388(5) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C16 H16 0.9500 . ? C16 C17 1.383(5) . ? O1 C7 1.448(3) . ? C2 C1 1.397(4) . ? C2 C28 1.511(4) . ? C2 C3B 1.453(7) . ? C2 C3A 1.349(13) . ? C1 C7 1.512(4) . ? C1 C6 1.406(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.526(5) . ? C21B H21A 0.9900 . ? C21B H21B 0.9900 . ? C21B C5B 1.488(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.525(4) . ? C32 C33 1.529(5) . ? C6 C5B 1.456(7) . ? C6 C5A 1.344(14) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.512(10) . ? C3B C4B 1.392(8) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.420(8) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C4A C30A 1.533(14) . ? C4A C5A 1.380(18) . ? C4A C3A 1.418(17) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.459(17) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.537(7) . ? C30B C4B 1.492(8) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C22B C23B 1.381(8) . ? C22B C27B 1.399(9) . ? Br3B C25B 1.911(8) . ? Br3A C25A 1.866(14) . ? C27A H27A 0.9500 . ? C27A C26A 1.375(11) . ? C27A C22A 1.349(12) . ? C23A H23A 0.9500 . ? C23A C24A 1.416(11) . ? C23A C22A 1.410(12) . ? C24B H24B 0.9500 . ? C24B C25B 1.389(7) . ? C24B C23B 1.399(8) . ? C25A C26A 1.362(11) . ? C25A C24A 1.371(11) . ? C26A H26A 0.9500 . ? C25B C26B 1.369(7) . ? C26B H26B 0.9500 . ? C26B C27B 1.398(8) . ? C24A H24A 0.9500 . ? C23B H23B 0.9500 . ? C27B H27B 0.9500 . ? C5A C21A 1.514(17) . ? C3A C14A 1.53(2) . ? C21A H21C 0.9900 . ? C21A H21D 0.9900 . ? C21A O3A 1.484(18) . ? O3A C22A 1.53(2) . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? C14A O2A 1.427(14) . ? 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 C15 O2B C14B 121.1(6) . . ? C8 C9 H9 120.4 . . ? C8 C9 C10 119.2(3) . . ? C10 C9 H9 120.4 . . ? C22B O3B C21B 118.3(8) . . ? C9 C8 C13 119.9(3) . . ? O1 C8 C9 124.4(3) . . ? O1 C8 C13 115.7(3) . . ? C20 C15 O2B 118.6(4) . . ? C20 C15 C16 120.2(3) . . ? C16 C15 O2B 121.2(4) . . ? O2A C15 O2B 14.5(7) . . ? O2A C15 C20 133.1(6) . . ? O2A C15 C16 106.7(6) . . ? C18 C19 H19 120.2 . . ? C18 C19 C20 119.7(3) . . ? C20 C19 H19 120.2 . . ? C19 C18 Br2 119.1(2) . . ? C19 C18 C17 121.1(3) . . ? C17 C18 Br2 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C13 C12 H12 120.8 . . ? C13 C12 C11 118.4(3) . . ? C11 C12 H12 120.8 . . ? C8 C13 H13 119.3 . . ? C12 C13 C8 121.4(3) . . ? C12 C13 H13 119.3 . . ? C15 C20 C19 119.7(3) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C10 C11 Br1 119.4(2) . . ? C10 C11 C12 121.3(3) . . ? C12 C11 Br1 119.3(2) . . ? C15 C16 H16 119.8 . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16 119.8 . . ? C8 O1 C7 118.6(2) . . ? C1 C2 C28 121.5(3) . . ? C1 C2 C3B 118.8(3) . . ? C3B C2 C28 119.3(3) . . ? C3A C2 C1 118.2(6) . . ? C3A C2 C28 119.0(6) . . ? C3A C2 C3B 17.7(5) . . ? C2 C1 C7 118.8(3) . . ? C2 C1 C6 121.0(3) . . ? C6 C1 C7 120.0(3) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? C2 C28 C29 112.6(3) . . ? H28A C28 H28B 107.8 . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? O3B C21B H21A 109.4 . . ? O3B C21B H21B 109.4 . . ? O3B C21B C5B 111.3(6) . . ? H21A C21B H21B 108.0 . . ? C5B C21B H21A 109.4 . . ? C5B C21B H21B 109.4 . . ? O1 C7 C1 105.4(2) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.9 . . ? C6 C32 H32A 109.3 . . ? C6 C32 H32B 109.3 . . ? C6 C32 C33 111.7(3) . . ? C33 C32 H32A 109.3 . . ? C33 C32 H32B 109.3 . . ? C1 C6 C32 120.7(3) . . ? C1 C6 C5B 118.8(3) . . ? C5B C6 C32 119.9(3) . . ? C5A C6 C1 118.9(6) . . ? C5A C6 C32 119.5(6) . . ? C5A C6 C5B 18.1(5) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 119.0(5) . . ? C4B C3B C2 120.9(5) . . ? C4B C3B C14B 119.5(5) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 120.2(5) . . ? C4B C5B C21B 119.4(5) . . ? C4B C5B C6 120.0(5) . . ? O2B C14B C3B 105.3(6) . . ? O2B C14B H14A 110.7 . . ? O2B C14B H14B 110.7 . . ? C3B C14B H14A 110.7 . . ? C3B C14B H14B 110.7 . . ? H14A C14B H14B 108.8 . . ? C5A C4A C30A 122.3(10) . . ? C5A C4A C3A 119.9(11) . . ? C3A C4A C30A 117.8(10) . . ? C4A C30A H30A 110.4 . . ? C4A C30A H30B 110.4 . . ? H30A C30A H30B 108.6 . . ? C31A C30A C4A 106.6(11) . . ? C31A C30A H30A 110.4 . . ? C31A C30A H30B 110.4 . . ? H30C C30B H30D 107.2 . . ? C31B C30B H30C 108.0 . . ? C31B C30B H30D 108.0 . . ? C4B C30B H30C 108.0 . . ? C4B C30B H30D 108.0 . . ? C4B C30B C31B 117.4(5) . . ? C18 C17 H17 120.5 . . ? C16 C17 C18 119.0(3) . . ? C16 C17 H17 120.5 . . ? C3B C4B C5B 119.3(5) . . ? C3B C4B C30B 120.4(5) . . ? C5B C4B C30B 120.2(5) . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? O3B C22B C23B 115.7(7) . . ? O3B C22B C27B 123.8(7) . . ? C23B C22B C27B 120.4(7) . . ? C26A C27A H27A 119.7 . . ? C22A C27A H27A 119.7 . . ? C22A C27A C26A 120.6(11) . . ? C24A C23A H23A 121.2 . . ? C22A C23A H23A 121.2 . . ? C22A C23A C24A 117.6(11) . . ? C25B C24B H24B 120.3 . . ? C25B C24B C23B 119.4(6) . . ? C23B C24B H24B 120.3 . . ? C26A C25A Br3A 127.4(8) . . ? C26A C25A C24A 120.2(9) . . ? C24A C25A Br3A 112.1(7) . . ? C27A C26A H26A 119.6 . . ? C25A C26A C27A 120.7(10) . . ? C25A C26A H26A 119.6 . . ? C24B C25B Br3B 121.0(4) . . ? C26B C25B Br3B 117.8(4) . . ? C26B C25B C24B 121.3(5) . . ? C25B C26B H26B 120.2 . . ? C25B C26B C27B 119.7(6) . . ? C27B C26B H26B 120.2 . . ? C23A C24A H24A 120.0 . . ? C25A C24A C23A 120.0(10) . . ? C25A C24A H24A 120.0 . . ? C22B C23B C24B 119.6(7) . . ? C22B C23B H23B 120.2 . . ? C24B C23B H23B 120.2 . . ? C22B C27B H27B 120.3 . . ? C26B C27B C22B 119.5(7) . . ? C26B C27B H27B 120.3 . . ? C6 C5A C4A 120.2(11) . . ? C6 C5A C21A 120.2(10) . . ? C4A C5A C21A 119.4(11) . . ? C2 C3A C4A 120.4(10) . . ? C2 C3A C14A 119.5(11) . . ? C4A C3A C14A 120.0(11) . . ? C5A C21A H21C 109.9 . . ? C5A C21A H21D 109.9 . . ? H21C C21A H21D 108.3 . . ? O3A C21A C5A 109.0(11) . . ? O3A C21A H21C 109.9 . . ? O3A C21A H21D 109.9 . . ? C21A O3A C22A 111.8(12) . . ? C27A C22A C23A 120.5(12) . . ? C27A C22A O3A 125.7(11) . . ? C23A C22A O3A 113.8(11) . . ? C3A C14A H14C 110.5 . . ? C3A C14A H14D 110.5 . . ? H14C C14A H14D 108.7 . . ? O2A C14A C3A 106.3(11) . . ? O2A C14A H14C 110.5 . . ? O2A C14A H14D 110.5 . . ? C15 O2A C14A 109.1(11) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 179.0(2) . . . . ? O2B C15 C20 C19 178.9(4) . . . . ? O2B C15 C16 C17 -177.9(4) . . . . ? O2B C15 O2A C14A -6(3) . . . . ? C9 C8 C13 C12 -0.7(5) . . . . ? C9 C8 O1 C7 0.0(4) . . . . ? C9 C10 C11 Br1 178.5(2) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? O3B C21B C5B C6 78.9(8) . . . . ? O3B C21B C5B C4B -108.4(7) . . . . ? O3B C22B C23B C24B 172.2(7) . . . . ? O3B C22B C27B C26B -173.4(8) . . . . ? C8 C9 C10 C11 -1.0(5) . . . . ? C8 O1 C7 C1 174.6(2) . . . . ? C15 O2B C14B C3B -170.9(6) . . . . ? C15 C16 C17 C18 -1.3(5) . . . . ? C19 C18 C17 C16 0.1(5) . . . . ? C18 C19 C20 C15 -0.6(5) . . . . ? C10 C9 C8 C13 1.2(5) . . . . ? C10 C9 C8 O1 -178.4(3) . . . . ? C13 C8 O1 C7 -179.6(3) . . . . ? C13 C12 C11 Br1 -178.0(2) . . . . ? C13 C12 C11 C10 0.2(5) . . . . ? C20 C15 C16 C17 1.6(5) . . . . ? C20 C15 O2A C14A -13.3(16) . . . . ? C20 C19 C18 Br2 -178.0(2) . . . . ? C20 C19 C18 C17 0.8(5) . . . . ? C11 C12 C13 C8 0.0(5) . . . . ? C16 C15 C20 C19 -0.7(5) . . . . ? C16 C15 O2A C14A 168.0(9) . . . . ? O1 C8 C13 C12 178.9(3) . . . . ? C2 C1 C7 O1 -83.8(3) . . . . ? C2 C1 C6 C32 -177.7(3) . . . . ? C2 C1 C6 C5B -6.9(5) . . . . ? C2 C1 C6 C5A 13.7(7) . . . . ? C2 C3B C14B O2B 75.6(7) . . . . ? C2 C3B C4B C5B -2.7(9) . . . . ? C2 C3B C4B C30B 175.6(5) . . . . ? C2 C3A C14A O2A 97.1(13) . . . . ? C1 C2 C28 C29 -92.4(4) . . . . ? C1 C2 C3B C14B -178.4(5) . . . . ? C1 C2 C3B C4B -6.7(7) . . . . ? C1 C2 C3A C4A 2.8(12) . . . . ? C1 C2 C3A C14A 179.6(8) . . . . ? C1 C6 C5B C21B 169.9(5) . . . . ? C1 C6 C5B C4B -2.7(7) . . . . ? C1 C6 C5A C4A -12.7(13) . . . . ? C1 C6 C5A C21A 172.6(7) . . . . ? C28 C2 C1 C7 -0.9(4) . . . . ? C28 C2 C1 C6 -175.5(3) . . . . ? C28 C2 C3B C14B 8.6(7) . . . . ? C28 C2 C3B C4B -179.8(5) . . . . ? C28 C2 C3A C4A 170.0(8) . . . . ? C28 C2 C3A C14A -13.2(12) . . . . ? C21B O3B C22B C23B 166.4(7) . . . . ? C21B O3B C22B C27B -16.8(13) . . . . ? C21B C5B C4B C3B -165.3(6) . . . . ? C21B C5B C4B C30B 16.4(9) . . . . ? C7 C1 C6 C32 7.7(4) . . . . ? C7 C1 C6 C5B 178.5(4) . . . . ? C7 C1 C6 C5A -160.9(6) . . . . ? C32 C6 C5B C21B -19.2(7) . . . . ? C32 C6 C5B C4B 168.1(5) . . . . ? C32 C6 C5A C4A 178.6(8) . . . . ? C32 C6 C5A C21A 3.9(12) . . . . ? C6 C1 C7 O1 90.9(3) . . . . ? C6 C5B C4B C3B 7.4(9) . . . . ? C6 C5B C4B C30B -170.9(5) . . . . ? C6 C5A C21A O3A 61.3(13) . . . . ? C33 C32 C6 C1 87.1(4) . . . . ? C33 C32 C6 C5B -83.5(5) . . . . ? C33 C32 C6 C5A -104.3(7) . . . . ? C3B C2 C1 C7 -173.8(4) . . . . ? C3B C2 C1 C6 11.5(5) . . . . ? C3B C2 C28 C29 80.5(5) . . . . ? C3B C2 C3A C4A -94(3) . . . . ? C3B C2 C3A C14A 83(2) . . . . ? C5B C6 C5A C4A 82(2) . . . . ? C5B C6 C5A C21A -92(3) . . . . ? C14B O2B C15 C20 -12.0(8) . . . . ? C14B O2B C15 C16 167.5(5) . . . . ? C14B O2B C15 O2A 174(4) . . . . ? C14B C3B C4B C5B 168.9(6) . . . . ? C14B C3B C4B C30B -12.8(9) . . . . ? C4A C5A C21A O3A -113.5(13) . . . . ? C4A C3A C14A O2A -86.1(14) . . . . ? C30A C4A C5A C6 -174.6(10) . . . . ? C30A C4A C5A C21A 0.2(17) . . . . ? C30A C4A C3A C2 179.6(10) . . . . ? C30A C4A C3A C14A 2.8(16) . . . . ? C31B C30B C4B C3B 83.2(7) . . . . ? C31B C30B C4B C5B -98.5(6) . . . . ? C4B C3B C14B O2B -96.1(7) . . . . ? C22B O3B C21B C5B -168.4(7) . . . . ? Br3B C25B C26B C27B -179.9(5) . . . . ? Br3A C25A C26A C27A -176.1(9) . . . . ? Br3A C25A C24A C23A 179.7(9) . . . . ? C24B C25B C26B C27B -0.9(9) . . . . ? C26A C27A C22A C23A -3(2) . . . . ? C26A C27A C22A O3A 175.2(12) . . . . ? C26A C25A C24A C23A 4.9(16) . . . . ? C25B C24B C23B C22B 3.4(10) . . . . ? C25B C26B C27B C22B -0.4(10) . . . . ? C24A C23A C22A C27A 5.9(19) . . . . ? C24A C23A C22A O3A -172.9(11) . . . . ? C24A C25A C26A C27A -2.3(16) . . . . ? C23B C22B C27B C26B 3.2(11) . . . . ? C23B C24B C25B Br3B 178.3(5) . . . . ? C23B C24B C25B C26B -0.7(9) . . . . ? C27B C22B C23B C24B -4.7(12) . . . . ? C5A C6 C5B C21B 75(2) . . . . ? C5A C6 C5B C4B -98(3) . . . . ? C5A C4A C30A C31A 83.9(13) . . . . ? C5A C4A C3A C2 -1.9(16) . . . . ? C5A C4A C3A C14A -178.7(11) . . . . ? C5A C21A O3A C22A 174.8(11) . . . . ? C3A C2 C1 C7 166.0(6) . . . . ? C3A C2 C1 C6 -8.7(7) . . . . ? C3A C2 C28 C29 100.8(7) . . . . ? C3A C2 C3B C14B -85(2) . . . . ? C3A C2 C3B C4B 86(2) . . . . ? C3A C4A C30A C31A -97.7(12) . . . . ? C3A C4A C5A C6 7.0(17) . . . . ? C3A C4A C5A C21A -178.2(10) . . . . ? C3A C14A O2A C15 -171.7(10) . . . . ? C21A O3A C22A C27A -12(2) . . . . ? C21A O3A C22A C23A 166.9(12) . . . . ? C22A C27A C26A C25A 1.4(18) . . . . ? C22A C23A C24A C25A -6.6(17) . . . . ? O2A C15 C20 C19 -179.2(9) . . . . ? O2A C15 C16 C17 -179.5(7) . . . . ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.024 0.500 0.000 370 45 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962430' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-ea-190K _audit_creation_date 2013-12-23 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-ea, 190 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Br3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Br3 O5' _chemical_formula_weight 805.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.7089(4) _cell_length_b 13.3527(7) _cell_length_c 14.9175(9) _cell_angle_alpha 111.537(5) _cell_angle_beta 92.790(4) _cell_angle_gamma 90.451(4) _cell_volume 1796.06(16) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4568 _cell_measurement_temperature 190(2) _cell_measurement_theta_max 29.0955 _cell_measurement_theta_min 3.7129 _exptl_absorpt_coefficient_mu 3.409 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61417 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_unetI/netI 0.0609 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 25331 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.16 _diffrn_reflns_theta_min 4.06 _diffrn_ambient_temperature 190(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.870 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0460948000 _diffrn_orient_matrix_UB_12 0.0452054000 _diffrn_orient_matrix_UB_13 0.0192830000 _diffrn_orient_matrix_UB_21 0.0095076000 _diffrn_orient_matrix_UB_22 -0.0103193000 _diffrn_orient_matrix_UB_23 0.0432337000 _diffrn_orient_matrix_UB_31 0.0560266000 _diffrn_orient_matrix_UB_32 -0.0333730000 _diffrn_orient_matrix_UB_33 -0.0194942000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5440 _reflns_number_total 8439 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.063 _refine_diff_density_min -0.927 _refine_diff_density_rms 0.087 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 388 _refine_ls_number_reflns 8439 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0489 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1288 _refine_ls_wR_factor_ref 0.1424 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uiso(C25B) = Uiso(C25A) Uiso(C26B) = Uiso(C26A) Uiso(C24B) = Uiso(C24A) 4. Others Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(Br3A)=Sof(C27A)=Sof(H27A)=Sof(C23A)=Sof(H23A)=Sof(C25A)= Sof(C26A)=Sof(H26A)=Sof(C24A)=Sof(H24A)=Sof(C5A)=Sof(C3A)=Sof(C21A)=Sof(H21C)= Sof(H21D)=Sof(O3A)=Sof(C22A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(O2A)=1-FVAR(1) Sof(O2B)=Sof(O3B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C22B)=Sof(Br3B)=Sof(C24B)=Sof(H24B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C23B)=Sof(H23B)=Sof(C27B)=Sof(H27B)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 5.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C16(H16), C17(H17), C27A(H27A), C23A(H23A), C24B(H24B), C26A(H26A), C26B(H26B), C24A(H24A), C23B(H23B), C27B(H27B) 5.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.98432(4) 0.12000(4) 0.96918(3) 0.05026(15) Uani 1 1 d . . . Br1 Br 1.72165(4) 0.03844(4) 0.12698(3) 0.05074(15) Uani 1 1 d . . . O2B O 0.9180(7) 0.2813(4) 0.6393(4) 0.0362(16) Uiso 0.625(9) 1 d A 1 . C9 C 1.3102(3) 0.1082(3) 0.1783(3) 0.0336(8) Uani 1 1 d . . . H9 H 1.2231 0.0820 0.1459 0.040 Uiso 1 1 calc . . R O3B O 0.6886(9) 0.5352(7) 0.3646(7) 0.0349(16) Uani 0.625(9) 1 d A 1 . C8 C 1.3183(3) 0.1916(3) 0.2677(2) 0.0295(7) Uani 1 1 d . . . C15 C 0.9348(4) 0.2456(3) 0.7173(3) 0.0353(8) Uani 1 1 d . . . C19 C 0.8438(4) 0.1537(3) 0.8126(3) 0.0410(9) Uani 1 1 d . . . H19 H 0.7700 0.1156 0.8266 0.049 Uiso 1 1 calc A . R C18 C 0.9648(4) 0.1741(3) 0.8680(3) 0.0357(8) Uani 1 1 d A . . C10 C 1.4313(4) 0.0635(3) 0.1368(3) 0.0359(8) Uani 1 1 d . . . H10 H 1.4274 0.0057 0.0760 0.043 Uiso 1 1 calc . . R C12 C 1.5656(4) 0.1864(3) 0.2718(3) 0.0380(9) Uani 1 1 d . . . H12 H 1.6529 0.2131 0.3036 0.046 Uiso 1 1 calc . . R C13 C 1.4453(4) 0.2306(3) 0.3135(3) 0.0386(9) Uani 1 1 d . . . H13 H 1.4501 0.2885 0.3742 0.046 Uiso 1 1 calc . . R C20 C 0.8291(4) 0.1888(3) 0.7360(3) 0.0382(9) Uani 1 1 d A . . H20 H 0.7460 0.1734 0.6966 0.046 Uiso 1 1 calc . . R C11 C 1.5566(3) 0.1032(3) 0.1838(3) 0.0346(8) Uani 1 1 d . . . C16 C 1.0565(4) 0.2672(3) 0.7746(3) 0.0427(9) Uani 1 1 d A . . H16 H 1.1294 0.3075 0.7622 0.051 Uiso 1 1 calc . . R O1 O 1.2063(2) 0.24065(18) 0.31654(17) 0.0346(6) Uani 1 1 d A . . C2 C 0.9405(3) 0.2265(3) 0.4206(2) 0.0302(7) Uani 1 1 d . . . C1 C 0.9716(3) 0.2649(2) 0.3485(2) 0.0276(7) Uani 1 1 d A . . C28 C 1.0014(3) 0.1232(3) 0.4230(3) 0.0339(8) Uani 1 1 d A . . H28A H 1.0178 0.1300 0.4910 0.041 Uiso 1 1 calc . . R H28B H 1.0916 0.1128 0.3931 0.041 Uiso 1 1 calc . . R C21B C 0.7877(8) 0.5335(5) 0.4365(5) 0.0288(16) Uiso 0.625(9) 1 d A 1 . H21A H 0.7505 0.5683 0.5010 0.035 Uiso 0.625(9) 1 calc A 1 R H21B H 0.8717 0.5746 0.4338 0.035 Uiso 0.625(9) 1 calc A 1 R C7 C 1.0695(3) 0.2030(3) 0.2730(3) 0.0312(8) Uani 1 1 d . . . H7A H 1.0577 0.1245 0.2571 0.037 Uiso 1 1 calc A . R H7B H 1.0533 0.2182 0.2132 0.037 Uiso 1 1 calc . . R C32 C 0.9523(4) 0.4046(3) 0.2698(3) 0.0372(8) Uani 1 1 d A . . H32A H 1.0448 0.3813 0.2464 0.045 Uiso 1 1 calc . . R H32B H 0.9531 0.4843 0.2955 0.045 Uiso 1 1 calc . . R C6 C 0.9222(3) 0.3644(3) 0.3500(3) 0.0322(8) Uani 1 1 d . . . C33 C 0.8434(4) 0.3611(4) 0.1849(3) 0.0506(10) Uani 1 1 d . . . H33A H 0.8628 0.3910 0.1358 0.076 Uiso 1 1 calc A . GR H33B H 0.7515 0.3822 0.2084 0.076 Uiso 1 1 calc . . GR H33C H 0.8467 0.2823 0.1567 0.076 Uiso 1 1 calc . . GR C3B C 0.8351(8) 0.2778(5) 0.4868(5) 0.0259(16) Uani 0.625(9) 1 d A 1 . C29 C 0.9080(4) 0.0244(3) 0.3702(3) 0.0443(10) Uani 1 1 d . . . H29A H 0.9000 0.0123 0.3012 0.067 Uiso 1 1 calc A . GR H29B H 0.8164 0.0363 0.3964 0.067 Uiso 1 1 calc . . GR H29C H 0.9477 -0.0388 0.3790 0.067 Uiso 1 1 calc . . GR C5B C 0.8237(9) 0.4199(6) 0.4216(5) 0.0257(16) Uani 0.625(9) 1 d A 1 . C14B C 0.8051(9) 0.2398(7) 0.5661(6) 0.032(2) Uani 0.625(9) 1 d A 1 . H14A H 0.7160 0.2674 0.5933 0.038 Uiso 0.625(9) 1 calc A 1 R H14B H 0.8004 0.1601 0.5418 0.038 Uiso 0.625(9) 1 calc A 1 R C4A C 0.8393(14) 0.3950(11) 0.5036(9) 0.032(3) Uani 0.375(9) 1 d A 2 . C30A C 0.7646(10) 0.4681(8) 0.5941(8) 0.039(3) Uiso 0.375(9) 1 d A 2 . H30A H 0.7859 0.4454 0.6493 0.047 Uiso 0.375(9) 1 calc A 2 R H30B H 0.7959 0.5441 0.6125 0.047 Uiso 0.375(9) 1 calc A 2 R C30B C 0.6604(6) 0.4224(5) 0.5490(4) 0.0310(15) Uani 0.625(9) 1 d A 1 . H30C H 0.6008 0.3628 0.5509 0.037 Uiso 0.625(9) 1 calc A 1 R H30D H 0.6040 0.4643 0.5189 0.037 Uiso 0.625(9) 1 calc A 1 R C31B C 0.7012(6) 0.4961(5) 0.6535(4) 0.0364(17) Uani 0.625(9) 1 d A 1 . H31A H 0.7531 0.5593 0.6535 0.055 Uiso 0.625(9) 1 calc A 1 GR H31B H 0.7588 0.4566 0.6844 0.055 Uiso 0.625(9) 1 calc A 1 GR H31C H 0.6178 0.5193 0.6892 0.055 Uiso 0.625(9) 1 calc A 1 GR C17 C 1.0720(4) 0.2302(3) 0.8494(3) 0.0423(9) Uani 1 1 d . . . H17 H 1.1560 0.2435 0.8878 0.051 Uiso 1 1 calc A . R C4B C 0.7770(7) 0.3737(6) 0.4841(5) 0.0243(15) Uani 0.625(9) 1 d A 1 . C31A C 0.6162(15) 0.4571(13) 0.5693(11) 0.059(4) Uiso 0.375(9) 1 d A 2 . H31D H 0.5978 0.4683 0.5085 0.089 Uiso 0.375(9) 1 calc A 2 GR H31E H 0.5679 0.5110 0.6207 0.089 Uiso 0.375(9) 1 calc A 2 GR H31F H 0.5834 0.3848 0.5620 0.089 Uiso 0.375(9) 1 calc A 2 GR C22B C 0.6646(10) 0.6300(8) 0.3572(7) 0.031(3) Uiso 0.625(9) 1 d A 1 . Br3B Br 0.5218(6) 0.9503(4) 0.3268(5) 0.0954(14) Uani 0.625(9) 1 d A 1 . Br3A Br 0.5106(10) 0.9598(6) 0.3494(7) 0.0641(12) Uani 0.375(9) 1 d A 2 . C27A C 0.6898(13) 0.7384(8) 0.4488(10) 0.028(4) Uiso 0.375(9) 1 d A 2 . H27A H 0.7377 0.7367 0.5052 0.033 Uiso 0.375(9) 1 calc A 2 R C23A C 0.5861(14) 0.6452(11) 0.2904(10) 0.031(4) Uiso 0.375(9) 1 d A 2 . H23A H 0.5602 0.5801 0.2384 0.037 Uiso 0.375(9) 1 calc A 2 R C24B C 0.5464(7) 0.7186(5) 0.2640(5) 0.0359(12) Uiso 0.625(9) 1 d A 1 . H24B H 0.4933 0.7153 0.2078 0.043 Uiso 0.625(9) 1 calc A 1 R C25A C 0.5750(10) 0.8395(8) 0.3687(8) 0.0302(11) Uiso 0.375(9) 1 d A 2 . C26A C 0.6459(11) 0.8359(9) 0.4478(9) 0.0334(12) Uiso 0.375(9) 1 d A 2 . H26A H 0.6653 0.9001 0.5023 0.040 Uiso 0.375(9) 1 calc A 2 R C25B C 0.5787(6) 0.8167(5) 0.3366(5) 0.0302(11) Uiso 0.625(9) 1 d A 1 . C26B C 0.6565(7) 0.8231(5) 0.4186(5) 0.0334(12) Uiso 0.625(9) 1 d A 1 . H26B H 0.6786 0.8912 0.4678 0.040 Uiso 0.625(9) 1 calc A 1 R C24A C 0.5446(12) 0.7461(9) 0.2889(9) 0.0359(12) Uiso 0.375(9) 1 d A 2 . H24A H 0.4960 0.7499 0.2334 0.043 Uiso 0.375(9) 1 calc A 2 R C23B C 0.5917(10) 0.6256(8) 0.2739(7) 0.043(3) Uiso 0.625(9) 1 d A 1 . H23B H 0.5728 0.5580 0.2232 0.051 Uiso 0.625(9) 1 calc A 1 R C27B C 0.7023(8) 0.7288(6) 0.4285(6) 0.035(2) Uiso 0.625(9) 1 d A 1 . H27B H 0.7587 0.7321 0.4834 0.042 Uiso 0.625(9) 1 calc A 1 R C5A C 0.8670(12) 0.4312(11) 0.4316(10) 0.023(3) Uiso 0.375(9) 1 d A 2 . C3A C 0.8776(12) 0.2933(10) 0.4992(9) 0.020(3) Uiso 0.375(9) 1 d A 2 . C21A C 0.8321(13) 0.5445(9) 0.4380(8) 0.028(3) Uiso 0.375(9) 1 d A 2 . H21C H 0.7991 0.5861 0.5026 0.034 Uiso 0.375(9) 1 calc A 2 R H21D H 0.9158 0.5818 0.4289 0.034 Uiso 0.375(9) 1 calc A 2 R O3A O 0.7234(14) 0.5387(14) 0.3623(13) 0.036(4) Uiso 0.375(9) 1 d A 2 . C22A C 0.6670(17) 0.6439(12) 0.3713(10) 0.030(5) Uiso 0.375(9) 1 d A 2 . C14A C 0.8422(13) 0.2514(12) 0.5789(12) 0.020(3) Uiso 0.375(9) 1 d A 2 . H14C H 0.7547 0.2815 0.6074 0.024 Uiso 0.375(9) 1 calc A 2 R H14D H 0.8331 0.1718 0.5527 0.024 Uiso 0.375(9) 1 calc A 2 R O2A O 0.9539(10) 0.2868(7) 0.6487(6) 0.032(3) Uiso 0.375(9) 1 d A 2 . 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 Br2 0.0620(3) 0.0622(3) 0.0363(2) 0.0284(2) 0.00995(19) 0.0137(2) Br1 0.0326(2) 0.0706(3) 0.0446(3) 0.0152(2) 0.00717(17) 0.01030(18) C9 0.0294(17) 0.038(2) 0.032(2) 0.0119(16) 0.0010(15) 0.0015(15) O3B 0.032(4) 0.030(3) 0.049(4) 0.022(2) 0.001(3) 0.006(3) C8 0.0298(17) 0.0312(18) 0.0298(19) 0.0140(15) 0.0009(14) -0.0002(14) C15 0.048(2) 0.0292(19) 0.034(2) 0.0168(16) 0.0130(17) 0.0081(16) C19 0.037(2) 0.047(2) 0.051(2) 0.0317(19) 0.0104(18) 0.0050(17) C18 0.042(2) 0.038(2) 0.030(2) 0.0162(16) 0.0115(16) 0.0112(16) C10 0.0386(19) 0.037(2) 0.0291(19) 0.0089(15) 0.0006(15) 0.0005(16) C12 0.0309(18) 0.041(2) 0.037(2) 0.0101(17) -0.0041(15) -0.0026(15) C13 0.0338(18) 0.039(2) 0.032(2) 0.0015(16) -0.0032(15) -0.0040(16) C20 0.0349(19) 0.045(2) 0.045(2) 0.0280(18) 0.0064(16) 0.0062(16) C11 0.0283(17) 0.041(2) 0.037(2) 0.0180(17) 0.0006(15) 0.0038(15) C16 0.052(2) 0.037(2) 0.040(2) 0.0149(18) 0.0104(19) -0.0059(18) O1 0.0272(12) 0.0340(13) 0.0350(14) 0.0038(11) 0.0015(10) 0.0013(10) C2 0.0347(17) 0.0219(17) 0.034(2) 0.0113(14) -0.0016(15) 0.0018(14) C1 0.0301(16) 0.0233(17) 0.0257(18) 0.0049(14) -0.0009(14) -0.0001(13) C28 0.0356(18) 0.0265(18) 0.041(2) 0.0137(16) 0.0020(16) 0.0078(15) C7 0.0281(17) 0.0323(19) 0.0297(19) 0.0075(15) 0.0002(14) 0.0002(14) C32 0.041(2) 0.041(2) 0.036(2) 0.0216(17) 0.0053(17) 0.0046(16) C6 0.0332(18) 0.0358(19) 0.0314(19) 0.0170(16) -0.0006(15) 0.0025(15) C33 0.055(2) 0.067(3) 0.032(2) 0.021(2) 0.0024(18) 0.012(2) C3B 0.018(3) 0.028(4) 0.035(4) 0.015(3) -0.003(3) -0.006(3) C29 0.050(2) 0.030(2) 0.053(3) 0.0146(18) 0.0005(19) 0.0007(17) C5B 0.021(4) 0.028(4) 0.032(4) 0.016(3) -0.004(3) 0.003(3) C14B 0.027(4) 0.037(4) 0.035(4) 0.020(3) -0.013(3) -0.004(3) C4A 0.030(7) 0.040(7) 0.024(6) 0.009(5) 0.007(5) 0.006(6) C30B 0.029(3) 0.030(3) 0.035(3) 0.012(3) 0.007(3) 0.009(3) C31B 0.042(3) 0.034(3) 0.031(3) 0.008(3) 0.011(3) 0.005(3) C17 0.044(2) 0.046(2) 0.037(2) 0.0152(18) 0.0016(17) -0.0025(18) C4B 0.017(3) 0.025(3) 0.033(4) 0.014(3) -0.001(3) 0.004(3) Br3B 0.0478(11) 0.088(2) 0.198(4) 0.113(3) -0.032(2) -0.0122(15) Br3A 0.0494(18) 0.0429(15) 0.114(2) 0.0485(16) -0.0163(12) 0.0066(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br2 C18 1.900(4) . ? Br1 C11 1.910(3) . ? O2B C15 1.413(7) . ? O2B C14B 1.460(10) . ? C9 H9 0.9500 . ? C9 C8 1.387(5) . ? C9 C10 1.390(5) . ? O3B C21B 1.412(11) . ? O3B C22B 1.333(13) . ? C8 C13 1.380(5) . ? C8 O1 1.372(4) . ? C15 C20 1.370(5) . ? C15 C16 1.388(6) . ? C15 O2A 1.347(10) . ? C19 H19 0.9500 . ? C19 C18 1.368(5) . ? C19 C20 1.386(5) . ? C18 C17 1.375(5) . ? C10 H10 0.9500 . ? C10 C11 1.374(5) . ? C12 H12 0.9500 . ? C12 C13 1.382(5) . ? C12 C11 1.372(5) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C16 H16 0.9500 . ? C16 C17 1.379(5) . ? O1 C7 1.450(4) . ? C2 C1 1.394(5) . ? C2 C28 1.516(4) . ? C2 C3B 1.451(7) . ? C2 C3A 1.361(13) . ? C1 C7 1.513(4) . ? C1 C6 1.410(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.527(5) . ? C21B H21A 0.9900 . ? C21B H21B 0.9900 . ? C21B C5B 1.497(9) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.519(5) . ? C32 C33 1.543(5) . ? C6 C5B 1.461(8) . ? C6 C5A 1.356(14) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.487(11) . ? C3B C4B 1.417(9) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.383(10) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C4A C30A 1.563(15) . ? C4A C5A 1.367(19) . ? C4A C3A 1.390(18) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.463(18) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.537(9) . ? C30B C4B 1.516(9) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C22B C23B 1.380(9) . ? C22B C27B 1.390(10) . ? Br3B C25B 1.925(8) . ? Br3A C25A 1.842(14) . ? C27A H27A 0.9500 . ? C27A C26A 1.377(11) . ? C27A C22A 1.371(13) . ? C23A H23A 0.9500 . ? C23A C24A 1.418(12) . ? C23A C22A 1.413(12) . ? C24B H24B 0.9500 . ? C24B C25B 1.381(8) . ? C24B C23B 1.377(9) . ? C25A C26A 1.354(11) . ? C25A C24A 1.389(11) . ? C26A H26A 0.9500 . ? C25B C26B 1.380(8) . ? C26B H26B 0.9500 . ? C26B C27B 1.395(8) . ? C24A H24A 0.9500 . ? C23B H23B 0.9500 . ? C27B H27B 0.9500 . ? C5A C21A 1.522(18) . ? C3A C14A 1.54(2) . ? C21A H21C 0.9900 . ? C21A H21D 0.9900 . ? C21A O3A 1.49(2) . ? O3A C22A 1.47(2) . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? C14A O2A 1.416(16) . ? 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 C15 O2B C14B 121.3(5) . . ? C8 C9 H9 120.5 . . ? C8 C9 C10 119.1(3) . . ? C10 C9 H9 120.5 . . ? C22B O3B C21B 117.3(8) . . ? C13 C8 C9 120.1(3) . . ? O1 C8 C9 124.3(3) . . ? O1 C8 C13 115.5(3) . . ? C20 C15 O2B 119.2(4) . . ? C20 C15 C16 119.9(3) . . ? C16 C15 O2B 120.9(4) . . ? O2A C15 O2B 15.0(4) . . ? O2A C15 C20 134.0(5) . . ? O2A C15 C16 106.0(5) . . ? C18 C19 H19 120.1 . . ? C18 C19 C20 119.9(4) . . ? C20 C19 H19 120.1 . . ? C19 C18 Br2 118.8(3) . . ? C19 C18 C17 120.8(4) . . ? C17 C18 Br2 120.4(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.1 . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C11 C12 C13 118.8(3) . . ? C8 C13 C12 120.7(3) . . ? C8 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C20 C19 119.9(4) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C10 C11 Br1 119.2(3) . . ? C12 C11 Br1 119.3(3) . . ? C12 C11 C10 121.4(3) . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.1(4) . . ? C17 C16 H16 120.0 . . ? C8 O1 C7 118.5(2) . . ? C1 C2 C28 120.9(3) . . ? C1 C2 C3B 119.7(4) . . ? C3B C2 C28 118.9(4) . . ? C3A C2 C1 118.5(6) . . ? C3A C2 C28 119.3(6) . . ? C3A C2 C3B 18.4(5) . . ? C2 C1 C7 119.1(3) . . ? C2 C1 C6 120.8(3) . . ? C6 C1 C7 119.9(3) . . ? C2 C28 H28A 109.0 . . ? C2 C28 H28B 109.0 . . ? C2 C28 C29 112.8(3) . . ? H28A C28 H28B 107.8 . . ? C29 C28 H28A 109.0 . . ? C29 C28 H28B 109.0 . . ? O3B C21B H21A 109.6 . . ? O3B C21B H21B 109.6 . . ? O3B C21B C5B 110.2(6) . . ? H21A C21B H21B 108.1 . . ? C5B C21B H21A 109.6 . . ? C5B C21B H21B 109.6 . . ? O1 C7 C1 105.0(3) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 108.0 . . ? C6 C32 H32A 109.4 . . ? C6 C32 H32B 109.4 . . ? C6 C32 C33 111.3(3) . . ? C33 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C1 C6 C32 120.8(3) . . ? C1 C6 C5B 118.3(4) . . ? C5B C6 C32 120.1(4) . . ? C5A C6 C1 118.3(7) . . ? C5A C6 C32 120.0(7) . . ? C5A C6 C5B 17.7(5) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 119.9(6) . . ? C4B C3B C2 119.0(6) . . ? C4B C3B C14B 120.3(6) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 119.6(6) . . ? C4B C5B C21B 119.3(6) . . ? C4B C5B C6 120.6(6) . . ? O2B C14B C3B 106.4(7) . . ? O2B C14B H14A 110.5 . . ? O2B C14B H14B 110.5 . . ? C3B C14B H14A 110.5 . . ? C3B C14B H14B 110.5 . . ? H14A C14B H14B 108.6 . . ? C5A C4A C30A 120.5(11) . . ? C5A C4A C3A 121.4(11) . . ? C3A C4A C30A 118.1(11) . . ? C4A C30A H30A 110.1 . . ? C4A C30A H30B 110.1 . . ? H30A C30A H30B 108.5 . . ? C31A C30A C4A 107.8(11) . . ? C31A C30A H30A 110.1 . . ? C31A C30A H30B 110.1 . . ? H30C C30B H30D 107.3 . . ? C31B C30B H30C 108.1 . . ? C31B C30B H30D 108.1 . . ? C4B C30B H30C 108.1 . . ? C4B C30B H30D 108.1 . . ? C4B C30B C31B 116.8(5) . . ? C18 C17 C16 119.5(4) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C3B C4B C30B 118.5(6) . . ? C5B C4B C3B 120.4(6) . . ? C5B C4B C30B 121.1(6) . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? O3B C22B C23B 115.5(8) . . ? O3B C22B C27B 124.1(8) . . ? C23B C22B C27B 120.3(9) . . ? C26A C27A H27A 118.8 . . ? C22A C27A H27A 118.8 . . ? C22A C27A C26A 122.5(12) . . ? C24A C23A H23A 120.9 . . ? C22A C23A H23A 120.9 . . ? C22A C23A C24A 118.3(12) . . ? C25B C24B H24B 120.3 . . ? C23B C24B H24B 120.3 . . ? C23B C24B C25B 119.4(7) . . ? C26A C25A Br3A 127.4(8) . . ? C26A C25A C24A 120.8(10) . . ? C24A C25A Br3A 111.8(8) . . ? C27A C26A H26A 120.2 . . ? C25A C26A C27A 119.6(10) . . ? C25A C26A H26A 120.2 . . ? C24B C25B Br3B 121.8(5) . . ? C26B C25B Br3B 117.1(5) . . ? C26B C25B C24B 121.1(6) . . ? C25B C26B H26B 120.3 . . ? C25B C26B C27B 119.4(6) . . ? C27B C26B H26B 120.3 . . ? C23A C24A H24A 120.1 . . ? C25A C24A C23A 119.9(11) . . ? C25A C24A H24A 120.1 . . ? C22B C23B H23B 119.9 . . ? C24B C23B C22B 120.3(9) . . ? C24B C23B H23B 119.9 . . ? C22B C27B C26B 119.2(8) . . ? C22B C27B H27B 120.4 . . ? C26B C27B H27B 120.4 . . ? C6 C5A C4A 120.0(11) . . ? C6 C5A C21A 118.1(11) . . ? C4A C5A C21A 121.8(11) . . ? C2 C3A C4A 119.8(11) . . ? C2 C3A C14A 118.9(10) . . ? C4A C3A C14A 121.2(11) . . ? C5A C21A H21C 109.7 . . ? C5A C21A H21D 109.7 . . ? H21C C21A H21D 108.2 . . ? O3A C21A C5A 109.6(11) . . ? O3A C21A H21C 109.7 . . ? O3A C21A H21D 109.7 . . ? C22A O3A C21A 114.0(13) . . ? C27A C22A C23A 118.7(13) . . ? C27A C22A O3A 125.8(12) . . ? C23A C22A O3A 115.5(12) . . ? C3A C14A H14C 110.7 . . ? C3A C14A H14D 110.7 . . ? H14C C14A H14D 108.8 . . ? O2A C14A C3A 105.1(10) . . ? O2A C14A H14C 110.7 . . ? O2A C14A H14D 110.7 . . ? C15 O2A C14A 108.3(9) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 178.9(3) . . . . ? O2B C15 C20 C19 -179.6(4) . . . . ? O2B C15 C16 C17 -179.0(4) . . . . ? O2B C15 O2A C14A -16.5(17) . . . . ? C9 C8 C13 C12 -0.9(6) . . . . ? C9 C8 O1 C7 0.5(5) . . . . ? C9 C10 C11 Br1 178.5(3) . . . . ? C9 C10 C11 C12 0.2(6) . . . . ? O3B C21B C5B C6 80.6(8) . . . . ? O3B C21B C5B C4B -107.5(8) . . . . ? O3B C22B C23B C24B 171.9(9) . . . . ? O3B C22B C27B C26B -171.7(9) . . . . ? C8 C9 C10 C11 -0.8(5) . . . . ? C8 O1 C7 C1 174.4(3) . . . . ? C15 O2B C14B C3B -169.2(5) . . . . ? C15 C16 C17 C18 -1.4(6) . . . . ? C19 C18 C17 C16 0.6(5) . . . . ? C18 C19 C20 C15 -1.4(6) . . . . ? C10 C9 C8 C13 1.2(5) . . . . ? C10 C9 C8 O1 -178.8(3) . . . . ? C13 C8 O1 C7 -179.4(3) . . . . ? C13 C12 C11 Br1 -178.2(3) . . . . ? C13 C12 C11 C10 0.1(6) . . . . ? C20 C15 C16 C17 0.9(5) . . . . ? C20 C15 O2A C14A -7.1(11) . . . . ? C20 C19 C18 Br2 -177.5(3) . . . . ? C20 C19 C18 C17 0.8(6) . . . . ? C11 C12 C13 C8 0.3(6) . . . . ? C16 C15 C20 C19 0.5(5) . . . . ? C16 C15 O2A C14A 170.3(7) . . . . ? O1 C8 C13 C12 179.0(3) . . . . ? C2 C1 C7 O1 -84.5(4) . . . . ? C2 C1 C6 C32 -178.1(3) . . . . ? C2 C1 C6 C5B -7.6(6) . . . . ? C2 C1 C6 C5A 12.5(7) . . . . ? C2 C3B C14B O2B 75.7(8) . . . . ? C2 C3B C4B C5B -2.3(10) . . . . ? C2 C3B C4B C30B 176.0(6) . . . . ? C2 C3A C14A O2A 95.5(12) . . . . ? C1 C2 C28 C29 -92.7(4) . . . . ? C1 C2 C3B C14B -177.8(6) . . . . ? C1 C2 C3B C4B -7.3(8) . . . . ? C1 C2 C3A C4A 3.4(12) . . . . ? C1 C2 C3A C14A 179.7(8) . . . . ? C1 C6 C5B C21B 169.6(5) . . . . ? C1 C6 C5B C4B -2.1(9) . . . . ? C1 C6 C5A C4A -10.8(13) . . . . ? C1 C6 C5A C21A 171.7(7) . . . . ? C28 C2 C1 C7 -1.1(5) . . . . ? C28 C2 C1 C6 -175.9(3) . . . . ? C28 C2 C3B C14B 10.2(8) . . . . ? C28 C2 C3B C4B -179.4(5) . . . . ? C28 C2 C3A C4A 170.7(8) . . . . ? C28 C2 C3A C14A -13.1(12) . . . . ? C21B O3B C22B C23B 166.1(9) . . . . ? C21B O3B C22B C27B -17.0(15) . . . . ? C21B C5B C4B C3B -164.8(6) . . . . ? C21B C5B C4B C30B 16.9(10) . . . . ? C7 C1 C6 C32 7.2(5) . . . . ? C7 C1 C6 C5B 177.7(4) . . . . ? C7 C1 C6 C5A -162.2(6) . . . . ? C32 C6 C5B C21B -19.8(8) . . . . ? C32 C6 C5B C4B 168.5(6) . . . . ? C32 C6 C5A C4A 179.7(9) . . . . ? C32 C6 C5A C21A 2.2(12) . . . . ? C6 C1 C7 O1 90.3(4) . . . . ? C6 C5B C4B C3B 6.9(11) . . . . ? C6 C5B C4B C30B -171.3(6) . . . . ? C6 C5A C21A O3A 63.4(13) . . . . ? C33 C32 C6 C1 86.9(4) . . . . ? C33 C32 C6 C5B -83.4(5) . . . . ? C33 C32 C6 C5A -103.9(7) . . . . ? C3B C2 C1 C7 -173.0(4) . . . . ? C3B C2 C1 C6 12.3(6) . . . . ? C3B C2 C28 C29 79.2(5) . . . . ? C3B C2 C3A C4A -95(3) . . . . ? C3B C2 C3A C14A 81(2) . . . . ? C5B C6 C5A C4A 84(3) . . . . ? C5B C6 C5A C21A -93(3) . . . . ? C14B O2B C15 C20 -13.7(7) . . . . ? C14B O2B C15 C16 166.2(5) . . . . ? C14B O2B C15 O2A 159(2) . . . . ? C14B C3B C4B C5B 168.1(7) . . . . ? C14B C3B C4B C30B -13.6(10) . . . . ? C4A C5A C21A O3A -114.1(14) . . . . ? C4A C3A C14A O2A -88.3(13) . . . . ? C30A C4A C5A C6 -174.9(10) . . . . ? C30A C4A C5A C21A 2.6(18) . . . . ? C30A C4A C3A C2 178.7(10) . . . . ? C30A C4A C3A C14A 2.6(17) . . . . ? C31B C30B C4B C3B 84.3(8) . . . . ? C31B C30B C4B C5B -97.5(8) . . . . ? C4B C3B C14B O2B -94.6(8) . . . . ? C22B O3B C21B C5B -168.0(8) . . . . ? Br3B C25B C26B C27B -179.0(6) . . . . ? Br3A C25A C26A C27A -178.1(10) . . . . ? Br3A C25A C24A C23A 180.0(10) . . . . ? C24B C25B C26B C27B -0.5(10) . . . . ? C26A C27A C22A C23A -5(2) . . . . ? C26A C27A C22A O3A 172.8(14) . . . . ? C26A C25A C24A C23A 1.0(17) . . . . ? C25B C24B C23B C22B 2.4(13) . . . . ? C25B C26B C27B C22B -2.3(11) . . . . ? C24A C23A C22A C27A 7(2) . . . . ? C24A C23A C22A O3A -171.5(13) . . . . ? C24A C25A C26A C27A 0.7(17) . . . . ? C23B C22B C27B C26B 5.0(14) . . . . ? C23B C24B C25B Br3B 178.9(7) . . . . ? C23B C24B C25B C26B 0.4(10) . . . . ? C27B C22B C23B C24B -5.1(15) . . . . ? C5A C6 C5B C21B 75(3) . . . . ? C5A C6 C5B C4B -97(3) . . . . ? C5A C4A C30A C31A 83.2(14) . . . . ? C5A C4A C3A C2 -1.9(17) . . . . ? C5A C4A C3A C14A -178.0(11) . . . . ? C5A C21A O3A C22A 171.3(12) . . . . ? C3A C2 C1 C7 166.0(6) . . . . ? C3A C2 C1 C6 -8.8(7) . . . . ? C3A C2 C28 C29 100.3(7) . . . . ? C3A C2 C3B C14B -86(2) . . . . ? C3A C2 C3B C4B 84(2) . . . . ? C3A C4A C30A C31A -97.4(13) . . . . ? C3A C4A C5A C6 5.7(18) . . . . ? C3A C4A C5A C21A -176.8(11) . . . . ? C3A C14A O2A C15 -175.3(8) . . . . ? C21A O3A C22A C27A -11(2) . . . . ? C21A O3A C22A C23A 167.1(14) . . . . ? C22A C27A C26A C25A 1(2) . . . . ? C22A C23A C24A C25A -5(2) . . . . ? O2A C15 C20 C19 177.6(6) . . . . ? O2A C15 C16 C17 -176.9(5) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.024 0.500 0.000 377 40 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962431' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-ea-226K _audit_creation_date 2013-12-23 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-ea, 226 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Br3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Br3 O5' _chemical_formula_weight 805.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.7426(4) _cell_length_b 13.3708(7) _cell_length_c 14.9451(9) _cell_angle_alpha 111.356(5) _cell_angle_beta 92.755(4) _cell_angle_gamma 90.399(4) _cell_volume 1810.44(17) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4064 _cell_measurement_temperature 226(2) _cell_measurement_theta_max 29.2296 _cell_measurement_theta_min 3.6873 _exptl_absorpt_coefficient_mu 3.382 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.67016 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_unetI/netI 0.0685 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 25667 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.29 _diffrn_reflns_theta_min 3.69 _diffrn_ambient_temperature 226(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.858 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0459363000 _diffrn_orient_matrix_UB_12 0.0450249000 _diffrn_orient_matrix_UB_13 0.0191760000 _diffrn_orient_matrix_UB_21 0.0094713000 _diffrn_orient_matrix_UB_22 -0.0104604000 _diffrn_orient_matrix_UB_23 0.0431020000 _diffrn_orient_matrix_UB_31 0.0558260000 _diffrn_orient_matrix_UB_32 -0.0333160000 _diffrn_orient_matrix_UB_33 -0.0194693000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5040 _reflns_number_total 8504 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.001 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.087 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 389 _refine_ls_number_reflns 8504 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1040 _refine_ls_R_factor_gt 0.0520 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1355 _refine_ls_wR_factor_ref 0.1543 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uiso(C25B) = Uiso(C25A) Uiso(C24B) = Uiso(C24A) 4. Others Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(Br3A)=Sof(C27A)=Sof(H27A)=Sof(C23A)=Sof(H23A)=Sof(C25A)= Sof(C26A)=Sof(H26A)=Sof(C24A)=Sof(H24A)=Sof(C5A)=Sof(C3A)=Sof(C21A)=Sof(H21C)= Sof(H21D)=Sof(O3A)=Sof(C22A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(O2A)=1-FVAR(1) Sof(O2B)=Sof(O3B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C22B)=Sof(Br3B)=Sof(C24B)=Sof(H24B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C23B)=Sof(H23B)=Sof(C27B)=Sof(H27B)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 5.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C16(H16), C17(H17), C27A(H27A), C23A(H23A), C24B(H24B), C26A(H26A), C26B(H26B), C24A(H24A), C23B(H23B), C27B(H27B) 5.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.98340(5) 0.11945(4) 0.96800(3) 0.05920(16) Uani 1 1 d . . . Br1 Br 1.72048(4) 0.03960(4) 0.12740(3) 0.05983(17) Uani 1 1 d . . . O2B O 0.9190(8) 0.2813(5) 0.6393(5) 0.040(2) Uiso 0.603(9) 1 d A 1 . C9 C 1.3115(4) 0.1094(3) 0.1791(3) 0.0361(8) Uani 1 1 d . . . H9 H 1.2259 0.0837 0.1468 0.043 Uiso 1 1 calc . . R O3B O 0.6886(9) 0.5354(7) 0.3644(7) 0.0417(19) Uani 0.603(9) 1 d A 1 . C8 C 1.3172(3) 0.1914(3) 0.2675(3) 0.0331(8) Uani 1 1 d . . . C15 C 0.9359(4) 0.2454(3) 0.7165(3) 0.0392(9) Uani 1 1 d . . . C19 C 0.8425(4) 0.1532(3) 0.8109(3) 0.0458(10) Uani 1 1 d . . . H19 H 0.7693 0.1160 0.8248 0.055 Uiso 1 1 calc A . R C18 C 0.9640(4) 0.1736(3) 0.8667(3) 0.0417(9) Uani 1 1 d A . . C10 C 1.4310(4) 0.0644(3) 0.1372(3) 0.0411(9) Uani 1 1 d . . . H10 H 1.4266 0.0075 0.0773 0.049 Uiso 1 1 calc . . R C12 C 1.5646(4) 0.1858(3) 0.2725(3) 0.0452(10) Uani 1 1 d . . . H12 H 1.6504 0.2116 0.3044 0.054 Uiso 1 1 calc . . R C13 C 1.4450(4) 0.2294(3) 0.3131(3) 0.0436(9) Uani 1 1 d . . . H13 H 1.4498 0.2863 0.3731 0.052 Uiso 1 1 calc . . R C20 C 0.8292(4) 0.1878(3) 0.7344(3) 0.0445(10) Uani 1 1 d A . . H20 H 0.7480 0.1722 0.6947 0.053 Uiso 1 1 calc . . R C11 C 1.5564(4) 0.1036(3) 0.1841(3) 0.0398(9) Uani 1 1 d . . . C16 C 1.0560(4) 0.2667(3) 0.7735(3) 0.0479(10) Uani 1 1 d A . . H16 H 1.1280 0.3064 0.7612 0.058 Uiso 1 1 calc . . R O1 O 1.2061(2) 0.24052(19) 0.31661(18) 0.0405(6) Uani 1 1 d A . . C2 C 0.9420(3) 0.2266(3) 0.4205(3) 0.0340(8) Uani 1 1 d . . . C1 C 0.9731(3) 0.2656(3) 0.3487(3) 0.0333(8) Uani 1 1 d A . . C28 C 1.0015(4) 0.1229(3) 0.4231(3) 0.0390(9) Uani 1 1 d A . . H28A H 1.0904 0.1120 0.3933 0.047 Uiso 1 1 calc . . R H28B H 1.0177 0.1296 0.4903 0.047 Uiso 1 1 calc . . R C21B C 0.7862(9) 0.5318(6) 0.4350(6) 0.039(2) Uiso 0.603(9) 1 d A 1 . H21A H 0.7488 0.5655 0.4986 0.047 Uiso 0.603(9) 1 calc A 1 R H21B H 0.8685 0.5733 0.4331 0.047 Uiso 0.603(9) 1 calc A 1 R C7 C 1.0700(3) 0.2042(3) 0.2739(3) 0.0359(8) Uani 1 1 d . . . H7A H 1.0579 0.1267 0.2582 0.043 Uiso 1 1 calc A . R H7B H 1.0542 0.2195 0.2149 0.043 Uiso 1 1 calc . . R C32 C 0.9531(4) 0.4041(3) 0.2700(3) 0.0441(9) Uani 1 1 d A . . H32A H 1.0442 0.3806 0.2468 0.053 Uiso 1 1 calc . . R H32B H 0.9544 0.4828 0.2951 0.053 Uiso 1 1 calc . . R C6 C 0.9239(4) 0.3648(3) 0.3502(3) 0.0348(8) Uani 1 1 d . . . C33 C 0.8459(5) 0.3620(4) 0.1858(3) 0.0598(12) Uani 1 1 d . . . H33A H 0.8649 0.3930 0.1381 0.090 Uiso 1 1 calc A . GR H33B H 0.7550 0.3820 0.2090 0.090 Uiso 1 1 calc . . GR H33C H 0.8499 0.2844 0.1570 0.090 Uiso 1 1 calc . . GR C3B C 0.8374(8) 0.2781(6) 0.4862(5) 0.0274(17) Uani 0.603(9) 1 d A 1 . C29 C 0.9081(4) 0.0258(3) 0.3712(3) 0.0525(11) Uani 1 1 d . . . H29A H 0.9027 0.0124 0.3028 0.079 Uiso 1 1 calc A . GR H29B H 0.8170 0.0392 0.3958 0.079 Uiso 1 1 calc . . GR H29C H 0.9450 -0.0365 0.3818 0.079 Uiso 1 1 calc . . GR C5B C 0.8254(9) 0.4199(6) 0.4217(6) 0.0305(18) Uani 0.603(9) 1 d A 1 . C14B C 0.8080(11) 0.2399(7) 0.5659(7) 0.0290(19) Uani 0.603(9) 1 d A 1 . H14A H 0.7196 0.2666 0.5925 0.035 Uiso 0.603(9) 1 calc A 1 R H14B H 0.8040 0.1612 0.5420 0.035 Uiso 0.603(9) 1 calc A 1 R C4A C 0.8420(13) 0.3954(10) 0.5038(10) 0.037(3) Uani 0.397(9) 1 d A 2 . C30A C 0.7642(10) 0.4667(8) 0.5945(8) 0.042(3) Uiso 0.397(9) 1 d A 2 . H30A H 0.7817 0.4416 0.6479 0.051 Uiso 0.397(9) 1 calc A 2 R H30B H 0.7956 0.5419 0.6152 0.051 Uiso 0.397(9) 1 calc A 2 R C30B C 0.6616(7) 0.4225(5) 0.5480(5) 0.0397(18) Uani 0.603(9) 1 d A 1 . H30C H 0.6020 0.3635 0.5489 0.048 Uiso 0.603(9) 1 calc A 1 R H30D H 0.6073 0.4645 0.5181 0.048 Uiso 0.603(9) 1 calc A 1 R C31B C 0.6994(7) 0.4946(5) 0.6524(5) 0.044(2) Uani 0.603(9) 1 d A 1 . H31A H 0.7597 0.5532 0.6534 0.065 Uiso 0.603(9) 1 calc A 1 GR H31B H 0.7461 0.4529 0.6853 0.065 Uiso 0.603(9) 1 calc A 1 GR H31C H 0.6165 0.5236 0.6846 0.065 Uiso 0.603(9) 1 calc A 1 GR C17 C 1.0712(4) 0.2301(3) 0.8485(3) 0.0502(10) Uani 1 1 d . . . H17 H 1.1536 0.2435 0.8868 0.060 Uiso 1 1 calc A . R C4B C 0.7786(8) 0.3740(6) 0.4842(6) 0.0266(16) Uani 0.603(9) 1 d A 1 . C31A C 0.6144(16) 0.4562(13) 0.5652(12) 0.068(5) Uiso 0.397(9) 1 d A 2 . H31D H 0.6005 0.4685 0.5054 0.102 Uiso 0.397(9) 1 calc A 2 GR H31E H 0.5646 0.5087 0.6149 0.102 Uiso 0.397(9) 1 calc A 2 GR H31F H 0.5809 0.3845 0.5563 0.102 Uiso 0.397(9) 1 calc A 2 GR C22B C 0.6644(10) 0.6290(8) 0.3573(7) 0.034(3) Uiso 0.603(9) 1 d A 1 . Br3B Br 0.5218(6) 0.9475(4) 0.3249(6) 0.1002(16) Uani 0.603(9) 1 d A 1 . Br3A Br 0.5115(9) 0.9604(6) 0.3508(7) 0.0760(14) Uani 0.397(9) 1 d A 2 . C27A C 0.6910(13) 0.7380(8) 0.4484(10) 0.033(4) Uiso 0.397(9) 1 d A 2 . H27A H 0.7387 0.7367 0.5041 0.039 Uiso 0.397(9) 1 calc A 2 R C23A C 0.5863(14) 0.6456(11) 0.2928(10) 0.039(4) Uiso 0.397(9) 1 d A 2 . H23A H 0.5588 0.5811 0.2427 0.046 Uiso 0.397(9) 1 calc A 2 R C24B C 0.5470(8) 0.7172(6) 0.2641(6) 0.0403(13) Uiso 0.603(9) 1 d A 1 . H24B H 0.4924 0.7132 0.2092 0.048 Uiso 0.603(9) 1 calc A 1 R C25A C 0.5737(10) 0.8372(8) 0.3680(8) 0.0326(11) Uiso 0.397(9) 1 d A 2 . C26A C 0.6455(11) 0.8335(9) 0.4461(9) 0.035(3) Uiso 0.397(9) 1 d A 2 . H26A H 0.6644 0.8972 0.4995 0.042 Uiso 0.397(9) 1 calc A 2 R C25B C 0.5805(6) 0.8152(6) 0.3350(5) 0.0326(11) Uiso 0.603(9) 1 d A 1 . C26B C 0.6575(8) 0.8222(6) 0.4170(6) 0.039(2) Uiso 0.603(9) 1 d A 1 . H26B H 0.6793 0.8895 0.4652 0.047 Uiso 0.603(9) 1 calc A 1 R C24A C 0.5454(12) 0.7455(9) 0.2902(9) 0.0403(13) Uiso 0.397(9) 1 d A 2 . H24A H 0.4987 0.7489 0.2349 0.048 Uiso 0.397(9) 1 calc A 2 R C23B C 0.5943(10) 0.6255(8) 0.2745(7) 0.044(3) Uiso 0.603(9) 1 d A 1 . H23B H 0.5783 0.5590 0.2239 0.053 Uiso 0.603(9) 1 calc A 1 R C27B C 0.7025(9) 0.7282(6) 0.4271(7) 0.037(3) Uiso 0.603(9) 1 d A 1 . H27B H 0.7586 0.7317 0.4812 0.044 Uiso 0.603(9) 1 calc A 1 R C5A C 0.8681(13) 0.4318(11) 0.4302(11) 0.028(4) Uiso 0.397(9) 1 d A 2 . C3A C 0.8815(12) 0.2942(10) 0.5001(10) 0.029(3) Uiso 0.397(9) 1 d A 2 . C21A C 0.8295(12) 0.5442(8) 0.4375(8) 0.028(2) Uiso 0.397(9) 1 d A 2 . H21C H 0.7954 0.5835 0.5012 0.033 Uiso 0.397(9) 1 calc A 2 R H21D H 0.9109 0.5831 0.4297 0.033 Uiso 0.397(9) 1 calc A 2 R O3A O 0.7237(12) 0.5386(12) 0.3634(11) 0.032(3) Uiso 0.397(9) 1 d A 2 . C22A C 0.6687(16) 0.6447(12) 0.3717(10) 0.037(5) Uiso 0.397(9) 1 d A 2 . C14A C 0.8444(17) 0.2545(15) 0.5813(15) 0.041(5) Uiso 0.397(9) 1 d A 2 . H14C H 0.7595 0.2869 0.6100 0.049 Uiso 0.397(9) 1 calc A 2 R H14D H 0.8318 0.1762 0.5562 0.049 Uiso 0.397(9) 1 calc A 2 R O2A O 0.9524(11) 0.2857(8) 0.6475(7) 0.042(3) Uiso 0.397(9) 1 d A 2 . 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 Br2 0.0734(3) 0.0720(3) 0.0434(3) 0.0332(2) 0.0113(2) 0.0154(2) Br1 0.0384(2) 0.0831(3) 0.0527(3) 0.0174(2) 0.00953(19) 0.0127(2) C9 0.0327(18) 0.042(2) 0.033(2) 0.0124(17) -0.0009(16) -0.0004(15) O3B 0.031(4) 0.035(3) 0.063(4) 0.024(2) -0.004(4) 0.004(3) C8 0.0324(18) 0.0313(18) 0.037(2) 0.0137(17) 0.0001(16) -0.0025(14) C15 0.052(2) 0.0337(19) 0.038(2) 0.0195(18) 0.0146(19) 0.0093(16) C19 0.042(2) 0.058(2) 0.053(3) 0.037(2) 0.0122(19) 0.0057(18) C18 0.051(2) 0.043(2) 0.037(2) 0.0190(18) 0.0156(19) 0.0146(17) C10 0.044(2) 0.045(2) 0.033(2) 0.0127(18) 0.0015(18) 0.0017(17) C12 0.035(2) 0.053(2) 0.045(2) 0.015(2) -0.0029(18) -0.0029(17) C13 0.040(2) 0.041(2) 0.039(2) 0.0019(18) -0.0022(18) -0.0016(16) C20 0.040(2) 0.050(2) 0.054(3) 0.032(2) 0.0054(19) 0.0072(17) C11 0.0367(19) 0.047(2) 0.040(2) 0.0212(19) 0.0060(17) 0.0056(16) C16 0.055(2) 0.043(2) 0.048(3) 0.019(2) 0.013(2) -0.0041(18) O1 0.0305(12) 0.0391(14) 0.0413(16) 0.0025(12) 0.0006(11) 0.0011(10) C2 0.0399(19) 0.0225(17) 0.038(2) 0.0096(16) -0.0024(17) 0.0032(14) C1 0.0352(18) 0.0259(17) 0.037(2) 0.0096(16) 0.0013(16) 0.0017(14) C28 0.040(2) 0.0319(19) 0.046(2) 0.0149(18) -0.0014(17) 0.0083(15) C7 0.0354(19) 0.0344(19) 0.037(2) 0.0126(17) -0.0002(16) 0.0024(15) C32 0.050(2) 0.045(2) 0.044(2) 0.0238(19) 0.0051(19) 0.0048(18) C6 0.0381(19) 0.0357(19) 0.033(2) 0.0151(17) 0.0022(16) 0.0005(15) C33 0.068(3) 0.076(3) 0.039(2) 0.025(2) 0.004(2) 0.017(2) C3B 0.016(3) 0.031(4) 0.037(4) 0.015(3) -0.002(3) -0.005(3) C29 0.057(3) 0.030(2) 0.068(3) 0.014(2) -0.001(2) 0.0018(17) C5B 0.025(4) 0.028(4) 0.042(5) 0.018(3) -0.004(4) 0.003(3) C14B 0.038(5) 0.026(4) 0.028(4) 0.016(3) -0.007(4) -0.003(3) C4A 0.029(6) 0.043(7) 0.037(7) 0.013(5) 0.005(6) 0.011(5) C30B 0.039(4) 0.032(4) 0.053(4) 0.019(3) 0.008(3) 0.016(3) C31B 0.056(4) 0.034(3) 0.037(4) 0.007(3) 0.017(3) 0.003(3) C17 0.050(2) 0.057(3) 0.042(2) 0.016(2) 0.001(2) -0.0010(19) C4B 0.023(4) 0.028(3) 0.033(4) 0.016(3) 0.001(3) 0.007(3) Br3B 0.0550(13) 0.090(3) 0.202(5) 0.115(3) -0.037(2) -0.0146(15) Br3A 0.0609(16) 0.0495(13) 0.133(3) 0.0539(17) -0.0153(14) 0.0115(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br2 C18 1.904(4) . ? Br1 C11 1.905(4) . ? O2B C15 1.405(8) . ? O2B C14B 1.454(13) . ? C9 H9 0.9400 . ? C9 C8 1.375(5) . ? C9 C10 1.383(5) . ? O3B C21B 1.400(12) . ? O3B C22B 1.316(13) . ? C8 C13 1.390(5) . ? C8 O1 1.370(4) . ? C15 C20 1.383(5) . ? C15 C16 1.379(6) . ? C15 O2A 1.340(11) . ? C19 H19 0.9400 . ? C19 C18 1.381(6) . ? C19 C20 1.381(5) . ? C18 C17 1.378(6) . ? C10 H10 0.9400 . ? C10 C11 1.378(5) . ? C12 H12 0.9400 . ? C12 C13 1.374(5) . ? C12 C11 1.375(5) . ? C13 H13 0.9400 . ? C20 H20 0.9400 . ? C16 H16 0.9400 . ? C16 C17 1.379(6) . ? O1 C7 1.444(4) . ? C2 C1 1.397(5) . ? C2 C28 1.519(5) . ? C2 C3B 1.445(8) . ? C2 C3A 1.368(13) . ? C1 C7 1.504(5) . ? C1 C6 1.406(5) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 C29 1.516(5) . ? C21B H21A 0.9800 . ? C21B H21B 0.9800 . ? C21B C5B 1.491(10) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 C6 1.511(5) . ? C32 C33 1.529(6) . ? C6 C5B 1.463(9) . ? C6 C5A 1.347(15) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C3B C14B 1.496(11) . ? C3B C4B 1.418(10) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C5B C4B 1.382(12) . ? C14B H14A 0.9800 . ? C14B H14B 0.9800 . ? C4A C30A 1.578(16) . ? C4A C5A 1.39(2) . ? C4A C3A 1.391(18) . ? C30A H30A 0.9800 . ? C30A H30B 0.9800 . ? C30A C31A 1.494(18) . ? C30B H30C 0.9800 . ? C30B H30D 0.9800 . ? C30B C31B 1.531(10) . ? C30B C4B 1.514(11) . ? C31B H31A 0.9700 . ? C31B H31B 0.9700 . ? C31B H31C 0.9700 . ? C17 H17 0.9400 . ? C31A H31D 0.9700 . ? C31A H31E 0.9700 . ? C31A H31F 0.9700 . ? C22B C23B 1.370(9) . ? C22B C27B 1.391(10) . ? Br3B C25B 1.918(9) . ? Br3A C25A 1.859(13) . ? C27A H27A 0.9400 . ? C27A C26A 1.366(11) . ? C27A C22A 1.359(13) . ? C23A H23A 0.9400 . ? C23A C24A 1.411(12) . ? C23A C22A 1.398(12) . ? C24B H24B 0.9400 . ? C24B C25B 1.376(8) . ? C24B C23B 1.372(9) . ? C25A C26A 1.348(11) . ? C25A C24A 1.363(11) . ? C26A H26A 0.9400 . ? C25B C26B 1.379(9) . ? C26B H26B 0.9400 . ? C26B C27B 1.391(8) . ? C24A H24A 0.9400 . ? C23B H23B 0.9400 . ? C27B H27B 0.9400 . ? C5A C21A 1.518(17) . ? C3A C14A 1.55(2) . ? C21A H21C 0.9800 . ? C21A H21D 0.9800 . ? C21A O3A 1.457(18) . ? O3A C22A 1.48(2) . ? C14A H14C 0.9800 . ? C14A H14D 0.9800 . ? C14A O2A 1.36(2) . ? 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 C15 O2B C14B 121.6(6) . . ? C8 C9 H9 119.8 . . ? C8 C9 C10 120.5(3) . . ? C10 C9 H9 119.8 . . ? C22B O3B C21B 118.2(8) . . ? C9 C8 C13 118.8(3) . . ? O1 C8 C9 125.6(3) . . ? O1 C8 C13 115.6(3) . . ? C20 C15 O2B 118.6(5) . . ? C16 C15 O2B 121.1(5) . . ? C16 C15 C20 120.2(4) . . ? O2A C15 O2B 13.9(5) . . ? O2A C15 C20 132.4(6) . . ? O2A C15 C16 107.3(5) . . ? C18 C19 H19 120.2 . . ? C18 C19 C20 119.5(4) . . ? C20 C19 H19 120.2 . . ? C19 C18 Br2 118.9(3) . . ? C17 C18 Br2 120.1(3) . . ? C17 C18 C19 121.0(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 C9 119.6(4) . . ? C11 C10 H10 120.2 . . ? C13 C12 H12 120.7 . . ? C13 C12 C11 118.7(4) . . ? C11 C12 H12 120.7 . . ? C8 C13 H13 119.3 . . ? C12 C13 C8 121.5(4) . . ? C12 C13 H13 119.3 . . ? C15 C20 H20 120.1 . . ? C19 C20 C15 119.7(4) . . ? C19 C20 H20 120.1 . . ? C10 C11 Br1 119.4(3) . . ? C12 C11 Br1 119.5(3) . . ? C12 C11 C10 121.0(3) . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.3(4) . . ? C17 C16 H16 119.9 . . ? C8 O1 C7 118.6(3) . . ? C1 C2 C28 121.5(3) . . ? C1 C2 C3B 119.2(4) . . ? C3B C2 C28 118.9(4) . . ? C3A C2 C1 118.2(6) . . ? C3A C2 C28 118.9(6) . . ? C3A C2 C3B 19.4(5) . . ? C2 C1 C7 118.8(3) . . ? C2 C1 C6 121.0(3) . . ? C6 C1 C7 120.1(3) . . ? C2 C28 H28A 109.0 . . ? C2 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C29 C28 C2 112.7(3) . . ? C29 C28 H28A 109.0 . . ? C29 C28 H28B 109.0 . . ? O3B C21B H21A 109.1 . . ? O3B C21B H21B 109.1 . . ? O3B C21B C5B 112.4(7) . . ? H21A C21B H21B 107.9 . . ? C5B C21B H21A 109.1 . . ? C5B C21B H21B 109.1 . . ? O1 C7 C1 105.3(3) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.9 . . ? C6 C32 H32A 109.2 . . ? C6 C32 H32B 109.2 . . ? C6 C32 C33 112.2(3) . . ? C33 C32 H32A 109.2 . . ? C33 C32 H32B 109.2 . . ? C1 C6 C32 120.5(3) . . ? C1 C6 C5B 118.3(4) . . ? C5B C6 C32 120.4(4) . . ? C5A C6 C1 119.3(7) . . ? C5A C6 C32 119.5(7) . . ? C5A C6 C5B 17.4(6) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 119.5(6) . . ? C4B C3B C2 120.0(6) . . ? C4B C3B C14B 119.8(7) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 119.9(7) . . ? C4B C5B C21B 118.9(7) . . ? C4B C5B C6 120.9(6) . . ? O2B C14B C3B 107.0(7) . . ? O2B C14B H14A 110.3 . . ? O2B C14B H14B 110.3 . . ? C3B C14B H14A 110.3 . . ? C3B C14B H14B 110.3 . . ? H14A C14B H14B 108.6 . . ? C5A C4A C30A 121.2(11) . . ? C5A C4A C3A 121.5(12) . . ? C3A C4A C30A 117.3(11) . . ? C4A C30A H30A 110.3 . . ? C4A C30A H30B 110.3 . . ? H30A C30A H30B 108.6 . . ? C31A C30A C4A 107.0(11) . . ? C31A C30A H30A 110.3 . . ? C31A C30A H30B 110.3 . . ? H30C C30B H30D 107.2 . . ? C31B C30B H30C 108.0 . . ? C31B C30B H30D 108.0 . . ? C4B C30B H30C 108.0 . . ? C4B C30B H30D 108.0 . . ? C4B C30B C31B 117.4(6) . . ? C18 C17 C16 119.2(4) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C3B C4B C30B 119.4(6) . . ? C5B C4B C3B 119.6(7) . . ? C5B C4B C30B 120.9(6) . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? O3B C22B C23B 115.8(9) . . ? O3B C22B C27B 125.1(9) . . ? C23B C22B C27B 119.1(9) . . ? C26A C27A H27A 119.3 . . ? C22A C27A H27A 119.3 . . ? C22A C27A C26A 121.4(12) . . ? C24A C23A H23A 120.8 . . ? C22A C23A H23A 120.8 . . ? C22A C23A C24A 118.4(12) . . ? C25B C24B H24B 120.4 . . ? C23B C24B H24B 120.4 . . ? C23B C24B C25B 119.1(7) . . ? C26A C25A Br3A 126.1(8) . . ? C26A C25A C24A 120.4(10) . . ? C24A C25A Br3A 113.5(8) . . ? C27A C26A H26A 119.7 . . ? C25A C26A C27A 120.6(11) . . ? C25A C26A H26A 119.7 . . ? C24B C25B Br3B 121.8(5) . . ? C24B C25B C26B 121.2(6) . . ? C26B C25B Br3B 117.0(5) . . ? C25B C26B H26B 120.6 . . ? C25B C26B C27B 118.9(7) . . ? C27B C26B H26B 120.6 . . ? C23A C24A H24A 120.1 . . ? C25A C24A C23A 119.9(10) . . ? C25A C24A H24A 120.1 . . ? C22B C23B C24B 121.2(9) . . ? C22B C23B H23B 119.4 . . ? C24B C23B H23B 119.4 . . ? C22B C27B C26B 120.1(8) . . ? C22B C27B H27B 120.0 . . ? C26B C27B H27B 120.0 . . ? C6 C5A C4A 119.2(12) . . ? C6 C5A C21A 120.1(12) . . ? C4A C5A C21A 120.7(12) . . ? C2 C3A C4A 119.7(11) . . ? C2 C3A C14A 120.1(11) . . ? C4A C3A C14A 119.9(12) . . ? C5A C21A H21C 109.7 . . ? C5A C21A H21D 109.7 . . ? H21C C21A H21D 108.2 . . ? O3A C21A C5A 110.1(10) . . ? O3A C21A H21C 109.7 . . ? O3A C21A H21D 109.7 . . ? C21A O3A C22A 113.8(11) . . ? C27A C22A C23A 118.9(13) . . ? C27A C22A O3A 125.7(12) . . ? C23A C22A O3A 115.4(11) . . ? C3A C14A H14C 110.6 . . ? C3A C14A H14D 110.6 . . ? H14C C14A H14D 108.7 . . ? O2A C14A C3A 105.7(11) . . ? O2A C14A H14C 110.6 . . ? O2A C14A H14D 110.6 . . ? C15 O2A C14A 110.0(11) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 178.7(3) . . . . ? O2B C15 C20 C19 -178.9(4) . . . . ? O2B C15 C16 C17 -179.5(4) . . . . ? O2B C15 O2A C14A -17(2) . . . . ? C9 C8 C13 C12 -1.0(6) . . . . ? C9 C8 O1 C7 0.5(5) . . . . ? C9 C10 C11 Br1 178.8(3) . . . . ? C9 C10 C11 C12 1.0(6) . . . . ? O3B C21B C5B C6 79.5(10) . . . . ? O3B C21B C5B C4B -107.1(10) . . . . ? O3B C22B C23B C24B 171.2(9) . . . . ? O3B C22B C27B C26B -172.4(10) . . . . ? C8 C9 C10 C11 -1.1(6) . . . . ? C8 O1 C7 C1 174.6(3) . . . . ? C15 O2B C14B C3B -168.9(6) . . . . ? C15 C16 C17 C18 -1.1(6) . . . . ? C19 C18 C17 C16 0.1(6) . . . . ? C18 C19 C20 C15 -2.1(6) . . . . ? C10 C9 C8 C13 1.2(5) . . . . ? C10 C9 C8 O1 -178.7(3) . . . . ? C13 C8 O1 C7 -179.3(3) . . . . ? C13 C12 C11 Br1 -178.6(3) . . . . ? C13 C12 C11 C10 -0.9(6) . . . . ? C20 C15 C16 C17 0.4(6) . . . . ? C20 C15 O2A C14A -5.3(13) . . . . ? C20 C19 C18 Br2 -177.1(3) . . . . ? C20 C19 C18 C17 1.5(6) . . . . ? C11 C12 C13 C8 0.9(6) . . . . ? C16 C15 C20 C19 1.2(6) . . . . ? C16 C15 O2A C14A 171.8(10) . . . . ? O1 C8 C13 C12 178.8(4) . . . . ? C2 C1 C7 O1 -84.4(4) . . . . ? C2 C1 C6 C32 -177.4(3) . . . . ? C2 C1 C6 C5B -7.6(6) . . . . ? C2 C1 C6 C5A 12.2(8) . . . . ? C2 C3B C14B O2B 76.2(8) . . . . ? C2 C3B C4B C5B -2.4(11) . . . . ? C2 C3B C4B C30B 175.4(7) . . . . ? C2 C3A C14A O2A 95.1(14) . . . . ? C1 C2 C28 C29 -92.9(4) . . . . ? C1 C2 C3B C14B -177.3(6) . . . . ? C1 C2 C3B C4B -6.9(9) . . . . ? C1 C2 C3A C4A 5.6(12) . . . . ? C1 C2 C3A C14A 179.7(9) . . . . ? C1 C6 C5B C21B 171.3(6) . . . . ? C1 C6 C5B C4B -1.9(10) . . . . ? C1 C6 C5A C4A -9.3(13) . . . . ? C1 C6 C5A C21A 173.0(7) . . . . ? C28 C2 C1 C7 -1.3(5) . . . . ? C28 C2 C1 C6 -176.2(3) . . . . ? C28 C2 C3B C14B 10.6(9) . . . . ? C28 C2 C3B C4B -179.0(5) . . . . ? C28 C2 C3A C4A 171.9(8) . . . . ? C28 C2 C3A C14A -13.9(13) . . . . ? C21B O3B C22B C23B 165.1(9) . . . . ? C21B O3B C22B C27B -16.0(16) . . . . ? C21B C5B C4B C3B -166.5(7) . . . . ? C21B C5B C4B C30B 15.7(12) . . . . ? C7 C1 C6 C32 7.8(5) . . . . ? C7 C1 C6 C5B 177.5(5) . . . . ? C7 C1 C6 C5A -162.6(7) . . . . ? C32 C6 C5B C21B -18.9(9) . . . . ? C32 C6 C5B C4B 167.8(6) . . . . ? C32 C6 C5A C4A -179.8(8) . . . . ? C32 C6 C5A C21A 2.5(12) . . . . ? C6 C1 C7 O1 90.5(4) . . . . ? C6 C5B C4B C3B 6.8(12) . . . . ? C6 C5B C4B C30B -170.9(7) . . . . ? C6 C5A C21A O3A 62.5(13) . . . . ? C33 C32 C6 C1 86.8(4) . . . . ? C33 C32 C6 C5B -82.7(6) . . . . ? C33 C32 C6 C5A -102.8(7) . . . . ? C3B C2 C1 C7 -173.1(4) . . . . ? C3B C2 C1 C6 11.9(6) . . . . ? C3B C2 C28 C29 79.0(6) . . . . ? C3B C2 C3A C4A -93(2) . . . . ? C3B C2 C3A C14A 82(2) . . . . ? C5B C6 C5A C4A 82(3) . . . . ? C5B C6 C5A C21A -95(3) . . . . ? C14B O2B C15 C20 -14.1(8) . . . . ? C14B O2B C15 C16 165.9(5) . . . . ? C14B O2B C15 O2A 156(3) . . . . ? C14B C3B C4B C5B 167.9(8) . . . . ? C14B C3B C4B C30B -14.3(11) . . . . ? C4A C5A C21A O3A -115.1(13) . . . . ? C4A C3A C14A O2A -90.7(14) . . . . ? C30A C4A C5A C6 -174.2(10) . . . . ? C30A C4A C5A C21A 3.5(17) . . . . ? C30A C4A C3A C2 176.2(10) . . . . ? C30A C4A C3A C14A 2.0(17) . . . . ? C31B C30B C4B C3B 83.7(8) . . . . ? C31B C30B C4B C5B -98.5(9) . . . . ? C4B C3B C14B O2B -94.2(8) . . . . ? C22B O3B C21B C5B -167.6(9) . . . . ? Br3B C25B C26B C27B -179.9(6) . . . . ? Br3A C25A C26A C27A -177.0(10) . . . . ? Br3A C25A C24A C23A -179.9(10) . . . . ? C24B C25B C26B C27B 0.5(11) . . . . ? C26A C27A C22A C23A -6(2) . . . . ? C26A C27A C22A O3A 174.4(14) . . . . ? C26A C25A C24A C23A 2.7(18) . . . . ? C25B C24B C23B C22B 5.3(14) . . . . ? C25B C26B C27B C22B -2.9(13) . . . . ? C24A C23A C22A C27A 9(2) . . . . ? C24A C23A C22A O3A -171.8(13) . . . . ? C24A C25A C26A C27A 0.0(18) . . . . ? C23B C22B C27B C26B 6.5(15) . . . . ? C23B C24B C25B Br3B 178.7(7) . . . . ? C23B C24B C25B C26B -1.6(12) . . . . ? C27B C22B C23B C24B -7.8(16) . . . . ? C5A C6 C5B C21B 73(3) . . . . ? C5A C6 C5B C4B -100(3) . . . . ? C5A C4A C30A C31A 79.5(14) . . . . ? C5A C4A C3A C2 -3.0(17) . . . . ? C5A C4A C3A C14A -177.2(12) . . . . ? C5A C21A O3A C22A 173.7(12) . . . . ? C3A C2 C1 C7 164.7(6) . . . . ? C3A C2 C1 C6 -10.2(7) . . . . ? C3A C2 C28 C29 101.2(7) . . . . ? C3A C2 C3B C14B -85(2) . . . . ? C3A C2 C3B C4B 86(2) . . . . ? C3A C4A C30A C31A -99.7(12) . . . . ? C3A C4A C5A C6 4.9(17) . . . . ? C3A C4A C5A C21A -177.4(11) . . . . ? C3A C14A O2A C15 -173.9(10) . . . . ? C21A O3A C22A C27A -12(2) . . . . ? C21A O3A C22A C23A 168.7(13) . . . . ? C22A C27A C26A C25A 2(2) . . . . ? C22A C23A C24A C25A -7(2) . . . . ? O2A C15 C20 C19 178.0(7) . . . . ? O2A C15 C16 C17 -177.1(5) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.027 0.500 0.000 386 46 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962432' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-ea-262K _audit_creation_date 2013-12-23 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-ea, 262 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Br3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Br3 O5' _chemical_formula_weight 805.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.7760(5) _cell_length_b 13.3875(7) _cell_length_c 14.9897(10) _cell_angle_alpha 111.204(6) _cell_angle_beta 92.694(5) _cell_angle_gamma 90.304(4) _cell_volume 1826.44(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3610 _cell_measurement_temperature 262(2) _cell_measurement_theta_max 29.1657 _cell_measurement_theta_min 3.6945 _exptl_absorpt_coefficient_mu 3.352 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.67157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_unetI/netI 0.0753 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 24831 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.23 _diffrn_reflns_theta_min 3.70 _diffrn_ambient_temperature 262(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.859 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0453634000 _diffrn_orient_matrix_UB_12 0.0450828000 _diffrn_orient_matrix_UB_13 0.0190808000 _diffrn_orient_matrix_UB_21 0.0094809000 _diffrn_orient_matrix_UB_22 -0.0104687000 _diffrn_orient_matrix_UB_23 0.0429783000 _diffrn_orient_matrix_UB_31 0.0559574000 _diffrn_orient_matrix_UB_32 -0.0330059000 _diffrn_orient_matrix_UB_33 -0.0192872000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4636 _reflns_number_total 8539 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.961 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.093 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 391 _refine_ls_number_reflns 8539 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0632 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1084P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1807 _refine_ls_wR_factor_ref 0.2057 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Others Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(Br3A)=Sof(C27A)=Sof(H27A)=Sof(C23A)=Sof(H23A)=Sof(C25A)= Sof(C26A)=Sof(H26A)=Sof(C24A)=Sof(H24A)=Sof(C5A)=Sof(C3A)=Sof(C21A)=Sof(H21C)= Sof(H21D)=Sof(O3A)=Sof(C22A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(O2A)=1-FVAR(1) Sof(O2B)=Sof(O3B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C22B)=Sof(Br3B)=Sof(C24B)=Sof(H24B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C23B)=Sof(H23B)=Sof(C27B)=Sof(H27B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C16(H16), C17(H17), C27A(H27A), C23A(H23A), C24B(H24B), C26A(H26A), C26B(H26B), C24A(H24A), C23B(H23B), C27B(H27B) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.98282(7) 0.11908(5) 0.96703(4) 0.0694(2) Uani 1 1 d . . . Br1 Br 1.71918(6) 0.04060(5) 0.12772(4) 0.0703(2) Uani 1 1 d . . . O2B O 0.9160(10) 0.2824(7) 0.6387(7) 0.049(3) Uiso 0.581(12) 1 d A 1 . C9 C 1.3106(5) 0.1092(4) 0.1791(3) 0.0424(11) Uani 1 1 d . . . H9 H 1.2262 0.0835 0.1476 0.051 Uiso 1 1 calc . . R O3B O 0.6903(15) 0.5360(10) 0.3674(11) 0.045(3) Uani 0.581(12) 1 d A 1 . C8 C 1.3178(5) 0.1917(4) 0.2681(3) 0.0406(11) Uani 1 1 d . . . C15 C 0.9349(5) 0.2442(3) 0.7154(3) 0.0440(11) Uani 1 1 d . . . C19 C 0.8429(6) 0.1533(5) 0.8105(4) 0.0620(15) Uani 1 1 d . . . H19 H 0.7703 0.1171 0.8242 0.074 Uiso 1 1 calc A . R C18 C 0.9643(5) 0.1725(4) 0.8662(3) 0.0479(12) Uani 1 1 d A . . C10 C 1.4306(5) 0.0658(4) 0.1382(3) 0.0511(13) Uani 1 1 d . . . H10 H 1.4264 0.0106 0.0786 0.061 Uiso 1 1 calc . . R C12 C 1.5626(5) 0.1861(4) 0.2723(4) 0.0527(13) Uani 1 1 d . . . H12 H 1.6471 0.2125 0.3032 0.063 Uiso 1 1 calc . . R C13 C 1.4445(5) 0.2289(4) 0.3138(3) 0.0504(12) Uani 1 1 d . . . H13 H 1.4492 0.2839 0.3735 0.060 Uiso 1 1 calc . . R C20 C 0.8305(5) 0.1885(4) 0.7340(4) 0.0511(13) Uani 1 1 d A . . H20 H 0.7502 0.1738 0.6953 0.061 Uiso 1 1 calc . . R C11 C 1.5558(5) 0.1028(4) 0.1838(3) 0.0456(11) Uani 1 1 d . . . C16 C 1.0546(6) 0.2648(4) 0.7722(4) 0.0567(14) Uani 1 1 d A . . H16 H 1.1256 0.3034 0.7596 0.068 Uiso 1 1 calc . . R O1 O 1.2059(3) 0.2411(2) 0.3166(2) 0.0492(8) Uani 1 1 d A . . C2 C 0.9423(5) 0.2266(3) 0.4205(3) 0.0390(10) Uani 1 1 d . . . C1 C 0.9737(5) 0.2656(3) 0.3493(3) 0.0393(10) Uani 1 1 d A . . C28 C 1.0018(5) 0.1234(3) 0.4233(3) 0.0429(11) Uani 1 1 d A . . H28A H 1.0161 0.1292 0.4894 0.052 Uiso 1 1 calc . . R H28B H 1.0903 0.1131 0.3949 0.052 Uiso 1 1 calc . . R C21B C 0.7873(12) 0.5310(8) 0.4343(8) 0.042(3) Uiso 0.581(12) 1 d A 1 . H21A H 0.7524 0.5641 0.4976 0.051 Uiso 0.581(12) 1 calc A 1 R H21B H 0.8682 0.5717 0.4313 0.051 Uiso 0.581(12) 1 calc A 1 R C7 C 1.0710(5) 0.2041(4) 0.2744(3) 0.0414(11) Uani 1 1 d . . . H7A H 1.0598 0.1277 0.2593 0.050 Uiso 1 1 calc A . R H7B H 1.0550 0.2190 0.2161 0.050 Uiso 1 1 calc . . R C32 C 0.9548(5) 0.4042(4) 0.2702(3) 0.0502(12) Uani 1 1 d A . . H32A H 1.0441 0.3800 0.2467 0.060 Uiso 1 1 calc . . R H32B H 0.9575 0.4819 0.2950 0.060 Uiso 1 1 calc . . R C6 C 0.9258(5) 0.3652(3) 0.3505(3) 0.0389(10) Uani 1 1 d . . . C33 C 0.8464(6) 0.3635(5) 0.1866(4) 0.0702(17) Uani 1 1 d . . . H33A H 0.8619 0.3975 0.1414 0.105 Uiso 1 1 calc A . GR H33B H 0.7568 0.3803 0.2107 0.105 Uiso 1 1 calc . . GR H33C H 0.8529 0.2873 0.1556 0.105 Uiso 1 1 calc . . GR C3B C 0.8363(12) 0.2778(9) 0.4862(8) 0.035(2) Uani 0.581(12) 1 d A 1 . C29 C 0.9084(6) 0.0256(4) 0.3694(4) 0.0643(15) Uani 1 1 d . . . H29A H 0.9033 0.0142 0.3023 0.097 Uiso 1 1 calc A . GR H29B H 0.8183 0.0381 0.3936 0.097 Uiso 1 1 calc . . GR H29C H 0.9450 -0.0365 0.3787 0.097 Uiso 1 1 calc . . GR C5B C 0.8269(14) 0.4186(9) 0.4203(8) 0.036(3) Uani 0.581(12) 1 d A 1 . C14B C 0.8047(13) 0.2400(10) 0.5646(9) 0.042(3) Uani 0.581(12) 1 d A 1 . H14A H 0.7172 0.2665 0.5902 0.051 Uiso 0.581(12) 1 calc A 1 R H14B H 0.8011 0.1623 0.5415 0.051 Uiso 0.581(12) 1 calc A 1 R C4A C 0.8460(17) 0.3963(13) 0.5042(12) 0.046(4) Uani 0.419(12) 1 d A 2 . C30A C 0.7678(13) 0.4660(10) 0.5935(9) 0.047(4) Uiso 0.419(12) 1 d A 2 . H30A H 0.7882 0.4427 0.6467 0.056 Uiso 0.419(12) 1 calc A 2 R H30B H 0.7961 0.5407 0.6126 0.056 Uiso 0.419(12) 1 calc A 2 R C30B C 0.6608(10) 0.4209(7) 0.5461(7) 0.048(3) Uani 0.581(12) 1 d A 1 . H30C H 0.6016 0.3629 0.5469 0.058 Uiso 0.581(12) 1 calc A 1 R H30D H 0.6081 0.4631 0.5166 0.058 Uiso 0.581(12) 1 calc A 1 R C31B C 0.7041(10) 0.4945(7) 0.6534(6) 0.052(3) Uani 0.581(12) 1 d A 1 . H31A H 0.7636 0.5518 0.6534 0.078 Uiso 0.581(12) 1 calc A 1 GR H31B H 0.7511 0.4524 0.6846 0.078 Uiso 0.581(12) 1 calc A 1 GR H31C H 0.6237 0.5238 0.6869 0.078 Uiso 0.581(12) 1 calc A 1 GR C17 C 1.0704(6) 0.2289(4) 0.8476(4) 0.0546(13) Uani 1 1 d . . . H17 H 1.1517 0.2426 0.8853 0.066 Uiso 1 1 calc A . R C4B C 0.7804(11) 0.3733(7) 0.4846(7) 0.031(2) Uani 0.581(12) 1 d A 1 . C31A C 0.6151(18) 0.4531(15) 0.5665(13) 0.065(5) Uiso 0.419(12) 1 d A 2 . H31D H 0.6005 0.4400 0.4994 0.097 Uiso 0.419(12) 1 calc A 2 GR H31E H 0.5698 0.5173 0.6030 0.097 Uiso 0.419(12) 1 calc A 2 GR H31F H 0.5785 0.3937 0.5800 0.097 Uiso 0.419(12) 1 calc A 2 GR C22B C 0.6658(17) 0.6285(11) 0.3573(10) 0.046(5) Uiso 0.581(12) 1 d A 1 . Br3B Br 0.5223(7) 0.9453(5) 0.3253(7) 0.118(2) Uani 0.581(12) 1 d A 1 . Br3A Br 0.5123(11) 0.9602(6) 0.3486(8) 0.0943(16) Uani 0.419(12) 1 d A 2 . C27A C 0.6904(16) 0.7346(9) 0.4461(12) 0.037(4) Uiso 0.419(12) 1 d A 2 . H27A H 0.7361 0.7322 0.5011 0.045 Uiso 0.419(12) 1 calc A 2 R C23A C 0.584(2) 0.6467(14) 0.2937(14) 0.064(7) Uiso 0.419(12) 1 d A 2 . H23A H 0.5535 0.5831 0.2456 0.077 Uiso 0.419(12) 1 calc A 2 R C24B C 0.5501(11) 0.7150(8) 0.2619(8) 0.052(3) Uiso 0.581(12) 1 d A 1 . H24B H 0.4997 0.7095 0.2060 0.063 Uiso 0.581(12) 1 calc A 1 R C25A C 0.5742(10) 0.8347(8) 0.3656(8) 0.025(3) Uiso 0.419(12) 1 d A 2 . C26A C 0.6473(12) 0.8308(9) 0.4446(10) 0.034(3) Uiso 0.419(12) 1 d A 2 . H26A H 0.6674 0.8935 0.4969 0.040 Uiso 0.419(12) 1 calc A 2 R C25B C 0.5794(9) 0.8111(8) 0.3309(8) 0.044(2) Uiso 0.581(12) 1 d A 1 . C26B C 0.6566(10) 0.8200(8) 0.4135(8) 0.045(3) Uiso 0.581(12) 1 d A 1 . H26B H 0.6770 0.8871 0.4601 0.054 Uiso 0.581(12) 1 calc A 1 R C24A C 0.5427(13) 0.7432(10) 0.2883(10) 0.037(3) Uiso 0.419(12) 1 d A 2 . H24A H 0.4954 0.7458 0.2339 0.044 Uiso 0.419(12) 1 calc A 2 R C23B C 0.5961(12) 0.6270(10) 0.2762(9) 0.040(3) Uiso 0.581(12) 1 d A 1 . H23B H 0.5790 0.5609 0.2274 0.048 Uiso 0.581(12) 1 calc A 1 R C27B C 0.7033(13) 0.7275(8) 0.4262(9) 0.046(4) Uiso 0.581(12) 1 d A 1 . H27B H 0.7587 0.7321 0.4798 0.055 Uiso 0.581(12) 1 calc A 1 R C5A C 0.8687(18) 0.4330(16) 0.4333(15) 0.040(6) Uiso 0.419(12) 1 d A 2 . C3A C 0.8802(15) 0.2929(13) 0.4979(12) 0.032(4) Uiso 0.419(12) 1 d A 2 . C21A C 0.8293(17) 0.5444(11) 0.4373(10) 0.038(4) Uiso 0.419(12) 1 d A 2 . H21C H 0.7944 0.5844 0.4994 0.046 Uiso 0.419(12) 1 calc A 2 R H21D H 0.9098 0.5825 0.4294 0.046 Uiso 0.419(12) 1 calc A 2 R O3A O 0.723(2) 0.5372(19) 0.3609(18) 0.045(5) Uiso 0.419(12) 1 d A 2 . C22A C 0.668(2) 0.6421(14) 0.3691(12) 0.036(6) Uiso 0.419(12) 1 d A 2 . C14A C 0.8455(17) 0.2500(15) 0.5777(15) 0.034(5) Uiso 0.419(12) 1 d A 2 . H14C H 0.7600 0.2790 0.6054 0.041 Uiso 0.419(12) 1 calc A 2 R H14D H 0.8370 0.1724 0.5520 0.041 Uiso 0.419(12) 1 calc A 2 R O2A O 0.9527(12) 0.2833(8) 0.6458(8) 0.041(3) Uiso 0.419(12) 1 d A 2 . 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 Br2 0.0864(5) 0.0846(4) 0.0502(3) 0.0385(3) 0.0132(3) 0.0172(3) Br1 0.0455(3) 0.0984(5) 0.0603(4) 0.0195(3) 0.0116(3) 0.0148(3) C9 0.037(3) 0.048(3) 0.038(3) 0.010(2) 0.000(2) 0.002(2) O3B 0.047(7) 0.030(4) 0.060(6) 0.020(3) -0.002(6) 0.009(5) C8 0.038(3) 0.043(3) 0.044(3) 0.018(2) 0.003(2) 0.003(2) C15 0.060(3) 0.035(2) 0.043(3) 0.020(2) 0.014(2) 0.008(2) C19 0.055(3) 0.079(4) 0.075(4) 0.053(3) 0.020(3) 0.010(3) C18 0.054(3) 0.054(3) 0.042(3) 0.023(2) 0.017(2) 0.014(2) C10 0.054(3) 0.055(3) 0.038(3) 0.009(2) 0.011(2) 0.006(2) C12 0.043(3) 0.058(3) 0.054(3) 0.017(3) -0.002(2) 0.002(2) C13 0.044(3) 0.053(3) 0.039(3) -0.001(2) -0.007(2) -0.002(2) C20 0.042(3) 0.064(3) 0.062(3) 0.040(3) 0.008(2) 0.010(2) C11 0.037(3) 0.058(3) 0.042(3) 0.019(2) -0.001(2) 0.001(2) C16 0.060(3) 0.059(3) 0.056(3) 0.026(3) 0.012(3) -0.003(3) O1 0.0385(18) 0.0481(19) 0.050(2) 0.0040(15) 0.0042(15) 0.0011(15) C2 0.045(3) 0.028(2) 0.042(2) 0.0100(19) -0.004(2) 0.0035(19) C1 0.040(3) 0.037(2) 0.040(2) 0.012(2) 0.004(2) 0.007(2) C28 0.046(3) 0.033(2) 0.050(3) 0.014(2) 0.002(2) 0.008(2) C7 0.039(3) 0.041(2) 0.043(3) 0.015(2) -0.001(2) 0.005(2) C32 0.059(3) 0.050(3) 0.048(3) 0.025(2) 0.009(2) 0.005(2) C6 0.044(3) 0.037(2) 0.037(2) 0.014(2) -0.002(2) 0.003(2) C33 0.080(4) 0.090(4) 0.039(3) 0.023(3) 0.002(3) 0.018(3) C3B 0.022(5) 0.042(6) 0.047(6) 0.024(4) 0.000(5) 0.000(4) C29 0.071(4) 0.039(3) 0.081(4) 0.020(3) 0.008(3) 0.001(3) C5B 0.041(7) 0.030(5) 0.039(6) 0.016(4) -0.007(5) 0.006(5) C14B 0.031(6) 0.049(6) 0.051(7) 0.026(5) -0.014(5) 0.005(5) C4A 0.031(8) 0.047(9) 0.054(9) 0.011(7) 0.016(8) 0.000(7) C30B 0.052(6) 0.043(5) 0.052(5) 0.018(4) 0.025(5) 0.032(5) C31B 0.061(6) 0.047(5) 0.044(5) 0.011(4) 0.014(4) 0.004(4) C17 0.050(3) 0.067(3) 0.049(3) 0.024(3) 0.003(2) -0.004(3) C4B 0.031(5) 0.021(4) 0.044(5) 0.015(4) 0.013(5) 0.008(4) Br3B 0.066(2) 0.098(3) 0.244(6) 0.135(4) -0.045(3) -0.016(2) Br3A 0.068(2) 0.0636(17) 0.166(3) 0.062(2) -0.0192(18) 0.0129(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br2 C18 1.895(5) . ? Br1 C11 1.894(5) . ? O2B C15 1.423(10) . ? O2B C14B 1.470(15) . ? C9 H9 0.9300 . ? C9 C8 1.388(6) . ? C9 C10 1.381(6) . ? O3B C21B 1.367(18) . ? O3B C22B 1.32(2) . ? C8 C13 1.385(7) . ? C8 O1 1.377(5) . ? C15 C20 1.358(7) . ? C15 C16 1.380(7) . ? C15 O2A 1.343(12) . ? C19 H19 0.9300 . ? C19 C18 1.386(8) . ? C19 C20 1.388(7) . ? C18 C17 1.376(7) . ? C10 H10 0.9300 . ? C10 C11 1.371(7) . ? C12 H12 0.9300 . ? C12 C13 1.365(7) . ? C12 C11 1.389(7) . ? C13 H13 0.9300 . ? C20 H20 0.9300 . ? C16 H16 0.9300 . ? C16 C17 1.382(7) . ? O1 C7 1.440(5) . ? C2 C1 1.393(6) . ? C2 C28 1.516(6) . ? C2 C3B 1.459(11) . ? C2 C3A 1.352(17) . ? C1 C7 1.511(6) . ? C1 C6 1.409(6) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C29 1.534(7) . ? C21B H21A 0.9700 . ? C21B H21B 0.9700 . ? C21B C5B 1.497(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C6 1.512(6) . ? C32 C33 1.538(8) . ? C6 C5B 1.450(13) . ? C6 C5A 1.39(2) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C3B C14B 1.482(16) . ? C3B C4B 1.401(13) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C5B C4B 1.402(16) . ? C14B H14A 0.9700 . ? C14B H14B 0.9700 . ? C4A C30A 1.564(19) . ? C4A C5A 1.35(3) . ? C4A C3A 1.40(2) . ? C30A H30A 0.9700 . ? C30A H30B 0.9700 . ? C30A C31A 1.52(2) . ? C30B H30C 0.9700 . ? C30B H30D 0.9700 . ? C30B C31B 1.588(13) . ? C30B C4B 1.519(13) . ? C31B H31A 0.9600 . ? C31B H31B 0.9600 . ? C31B H31C 0.9600 . ? C17 H17 0.9300 . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? C22B C23B 1.359(11) . ? C22B C27B 1.388(12) . ? Br3B C25B 1.913(10) . ? Br3A C25A 1.887(12) . ? C27A H27A 0.9300 . ? C27A C26A 1.365(12) . ? C27A C22A 1.361(14) . ? C23A H23A 0.9300 . ? C23A C24A 1.383(13) . ? C23A C22A 1.389(14) . ? C24B H24B 0.9300 . ? C24B C25B 1.347(11) . ? C24B C23B 1.347(11) . ? C25A C26A 1.371(12) . ? C25A C24A 1.369(13) . ? C26A H26A 0.9300 . ? C25B C26B 1.386(10) . ? C26B H26B 0.9300 . ? C26B C27B 1.396(10) . ? C24A H24A 0.9300 . ? C23B H23B 0.9300 . ? C27B H27B 0.9300 . ? C5A C21A 1.52(2) . ? C3A C14A 1.55(3) . ? C21A H21C 0.9700 . ? C21A H21D 0.9700 . ? C21A O3A 1.48(3) . ? O3A C22A 1.47(3) . ? C14A H14C 0.9700 . ? C14A H14D 0.9700 . ? C14A O2A 1.38(2) . ? 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 C15 O2B C14B 121.4(8) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C10 C9 C8 119.0(4) . . ? C22B O3B C21B 120.0(12) . . ? C13 C8 C9 119.6(4) . . ? O1 C8 C9 124.6(4) . . ? O1 C8 C13 115.8(4) . . ? C20 C15 O2B 118.7(6) . . ? C20 C15 C16 119.7(4) . . ? C16 C15 O2B 121.6(6) . . ? O2A C15 O2B 14.9(6) . . ? O2A C15 C20 132.9(7) . . ? O2A C15 C16 107.3(7) . . ? C18 C19 H19 120.2 . . ? C18 C19 C20 119.6(5) . . ? C20 C19 H19 120.2 . . ? C19 C18 Br2 119.2(4) . . ? C17 C18 Br2 120.6(4) . . ? C17 C18 C19 120.2(5) . . ? C9 C10 H10 119.4 . . ? C11 C10 C9 121.2(4) . . ? C11 C10 H10 119.4 . . ? C13 C12 H12 120.2 . . ? C13 C12 C11 119.6(5) . . ? C11 C12 H12 120.2 . . ? C8 C13 H13 119.5 . . ? C12 C13 C8 121.0(4) . . ? C12 C13 H13 119.5 . . ? C15 C20 C19 120.4(5) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C10 C11 Br1 120.6(4) . . ? C10 C11 C12 119.6(4) . . ? C12 C11 Br1 119.7(4) . . ? C15 C16 H16 119.5 . . ? C15 C16 C17 121.0(5) . . ? C17 C16 H16 119.5 . . ? C8 O1 C7 118.6(3) . . ? C1 C2 C28 121.4(4) . . ? C1 C2 C3B 119.4(5) . . ? C3B C2 C28 118.7(5) . . ? C3A C2 C1 118.0(8) . . ? C3A C2 C28 119.3(8) . . ? C3A C2 C3B 18.8(7) . . ? C2 C1 C7 118.9(4) . . ? C2 C1 C6 121.3(4) . . ? C6 C1 C7 119.6(4) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? C2 C28 C29 112.3(4) . . ? H28A C28 H28B 107.9 . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? O3B C21B H21A 109.0 . . ? O3B C21B H21B 109.0 . . ? O3B C21B C5B 112.9(10) . . ? H21A C21B H21B 107.8 . . ? C5B C21B H21A 109.0 . . ? C5B C21B H21B 109.0 . . ? O1 C7 C1 105.2(3) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.9 . . ? C6 C32 H32A 109.1 . . ? C6 C32 H32B 109.1 . . ? C6 C32 C33 112.3(4) . . ? C33 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? C1 C6 C32 120.8(4) . . ? C1 C6 C5B 117.7(6) . . ? C5B C6 C32 120.5(5) . . ? C5A C6 C1 118.1(9) . . ? C5A C6 C32 120.5(9) . . ? C5A C6 C5B 18.3(9) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 120.3(8) . . ? C4B C3B C2 119.3(8) . . ? C4B C3B C14B 119.6(9) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 120.0(10) . . ? C4B C5B C21B 118.1(10) . . ? C4B C5B C6 121.4(8) . . ? O2B C14B C3B 106.1(10) . . ? O2B C14B H14A 110.5 . . ? O2B C14B H14B 110.5 . . ? C3B C14B H14A 110.5 . . ? C3B C14B H14B 110.5 . . ? H14A C14B H14B 108.7 . . ? C5A C4A C30A 120.3(15) . . ? C5A C4A C3A 122.1(16) . . ? C3A C4A C30A 117.4(14) . . ? C4A C30A H30A 110.0 . . ? C4A C30A H30B 110.0 . . ? H30A C30A H30B 108.4 . . ? C31A C30A C4A 108.2(14) . . ? C31A C30A H30A 110.0 . . ? C31A C30A H30B 110.0 . . ? H30C C30B H30D 107.6 . . ? C31B C30B H30C 108.7 . . ? C31B C30B H30D 108.7 . . ? C4B C30B H30C 108.7 . . ? C4B C30B H30D 108.7 . . ? C4B C30B C31B 114.3(9) . . ? C18 C17 C16 119.1(5) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C3B C4B C5B 119.8(9) . . ? C3B C4B C30B 119.3(8) . . ? C5B C4B C30B 120.6(8) . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? O3B C22B C23B 118.4(12) . . ? O3B C22B C27B 123.8(12) . . ? C23B C22B C27B 117.8(13) . . ? C26A C27A H27A 119.2 . . ? C22A C27A H27A 119.2 . . ? C22A C27A C26A 121.6(14) . . ? C24A C23A H23A 119.1 . . ? C24A C23A C22A 121.8(16) . . ? C22A C23A H23A 119.1 . . ? C25B C24B H24B 121.0 . . ? C25B C24B C23B 117.9(10) . . ? C23B C24B H24B 121.0 . . ? C26A C25A Br3A 125.7(8) . . ? C24A C25A Br3A 113.3(8) . . ? C24A C25A C26A 120.9(9) . . ? C27A C26A C25A 119.7(11) . . ? C27A C26A H26A 120.1 . . ? C25A C26A H26A 120.1 . . ? C24B C25B Br3B 124.6(7) . . ? C24B C25B C26B 121.4(8) . . ? C26B C25B Br3B 114.1(7) . . ? C25B C26B H26B 120.3 . . ? C25B C26B C27B 119.4(9) . . ? C27B C26B H26B 120.3 . . ? C23A C24A H24A 121.1 . . ? C25A C24A C23A 117.8(12) . . ? C25A C24A H24A 121.1 . . ? C22B C23B H23B 117.8 . . ? C24B C23B C22B 124.4(12) . . ? C24B C23B H23B 117.8 . . ? C22B C27B C26B 118.8(11) . . ? C22B C27B H27B 120.6 . . ? C26B C27B H27B 120.6 . . ? C6 C5A C21A 117.7(16) . . ? C4A C5A C6 119.1(16) . . ? C4A C5A C21A 123.2(17) . . ? C2 C3A C4A 120.4(14) . . ? C2 C3A C14A 118.3(13) . . ? C4A C3A C14A 121.3(14) . . ? C5A C21A H21C 109.5 . . ? C5A C21A H21D 109.5 . . ? H21C C21A H21D 108.1 . . ? O3A C21A C5A 110.7(14) . . ? O3A C21A H21C 109.5 . . ? O3A C21A H21D 109.5 . . ? C22A O3A C21A 113.0(17) . . ? C27A C22A C23A 117.2(16) . . ? C27A C22A O3A 125.1(15) . . ? C23A C22A O3A 117.6(15) . . ? C3A C14A H14C 110.5 . . ? C3A C14A H14D 110.5 . . ? H14C C14A H14D 108.7 . . ? O2A C14A C3A 106.0(13) . . ? O2A C14A H14C 110.5 . . ? O2A C14A H14D 110.5 . . ? C15 O2A C14A 110.0(11) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 178.6(4) . . . . ? O2B C15 C20 C19 -177.6(6) . . . . ? O2B C15 C16 C17 178.8(6) . . . . ? O2B C15 O2A C14A -25(2) . . . . ? C9 C8 C13 C12 0.4(8) . . . . ? C9 C8 O1 C7 1.4(7) . . . . ? C9 C10 C11 Br1 178.8(4) . . . . ? C9 C10 C11 C12 -0.7(8) . . . . ? O3B C21B C5B C6 81.6(15) . . . . ? O3B C21B C5B C4B -106.8(14) . . . . ? O3B C22B C23B C24B 171.7(14) . . . . ? O3B C22B C27B C26B -171.7(15) . . . . ? C8 C9 C10 C11 0.0(7) . . . . ? C8 O1 C7 C1 174.1(4) . . . . ? C15 O2B C14B C3B -166.8(7) . . . . ? C15 C16 C17 C18 -0.5(8) . . . . ? C19 C18 C17 C16 -0.7(7) . . . . ? C18 C19 C20 C15 -1.9(8) . . . . ? C10 C9 C8 C13 0.1(7) . . . . ? C10 C9 C8 O1 -179.5(4) . . . . ? C13 C8 O1 C7 -178.2(4) . . . . ? C13 C12 C11 Br1 -178.3(4) . . . . ? C13 C12 C11 C10 1.2(8) . . . . ? C20 C15 C16 C17 0.5(7) . . . . ? C20 C15 O2A C14A -6.3(14) . . . . ? C20 C19 C18 Br2 -177.4(4) . . . . ? C20 C19 C18 C17 1.9(8) . . . . ? C11 C12 C13 C8 -1.1(8) . . . . ? C16 C15 C20 C19 0.8(7) . . . . ? C16 C15 O2A C14A 170.3(10) . . . . ? O1 C8 C13 C12 -179.9(5) . . . . ? C2 C1 C7 O1 -85.1(5) . . . . ? C2 C1 C6 C32 -177.0(4) . . . . ? C2 C1 C6 C5B -8.6(9) . . . . ? C2 C1 C6 C5A 12.1(11) . . . . ? C2 C3B C14B O2B 76.4(12) . . . . ? C2 C3B C4B C5B -0.2(16) . . . . ? C2 C3B C4B C30B 174.2(9) . . . . ? C2 C3A C14A O2A 95.6(16) . . . . ? C1 C2 C28 C29 -92.2(6) . . . . ? C1 C2 C3B C14B -177.9(8) . . . . ? C1 C2 C3B C4B -8.1(13) . . . . ? C1 C2 C3A C4A 1.6(16) . . . . ? C1 C2 C3A C14A -179.8(10) . . . . ? C1 C6 C5B C21B 171.4(8) . . . . ? C1 C6 C5B C4B 0.1(14) . . . . ? C1 C6 C5A C4A -8.1(18) . . . . ? C1 C6 C5A C21A 174.5(10) . . . . ? C28 C2 C1 C7 -1.0(7) . . . . ? C28 C2 C1 C6 -175.7(4) . . . . ? C28 C2 C3B C14B 10.2(13) . . . . ? C28 C2 C3B C4B 180.0(8) . . . . ? C28 C2 C3A C4A 168.8(10) . . . . ? C28 C2 C3A C14A -12.6(16) . . . . ? C21B O3B C22B C23B 163.7(14) . . . . ? C21B O3B C22B C27B -18(3) . . . . ? C21B C5B C4B C3B -167.3(10) . . . . ? C21B C5B C4B C30B 18.3(17) . . . . ? C7 C1 C6 C32 8.4(7) . . . . ? C7 C1 C6 C5B 176.8(7) . . . . ? C7 C1 C6 C5A -162.5(9) . . . . ? C32 C6 C5B C21B -20.1(14) . . . . ? C32 C6 C5B C4B 168.5(9) . . . . ? C32 C6 C5A C4A -179.0(11) . . . . ? C32 C6 C5A C21A 3.6(17) . . . . ? C6 C1 C7 O1 89.6(5) . . . . ? C6 C5B C4B C3B 4.2(17) . . . . ? C6 C5B C4B C30B -170.1(10) . . . . ? C6 C5A C21A O3A 61.5(19) . . . . ? C33 C32 C6 C1 87.1(5) . . . . ? C33 C32 C6 C5B -80.9(8) . . . . ? C33 C32 C6 C5A -102.2(10) . . . . ? C3B C2 C1 C7 -172.7(6) . . . . ? C3B C2 C1 C6 12.7(9) . . . . ? C3B C2 C28 C29 79.6(7) . . . . ? C3B C2 C3A C4A -98(3) . . . . ? C3B C2 C3A C14A 81(3) . . . . ? C5B C6 C5A C4A 85(4) . . . . ? C5B C6 C5A C21A -92(4) . . . . ? C14B O2B C15 C20 -16.6(10) . . . . ? C14B O2B C15 C16 165.2(7) . . . . ? C14B O2B C15 O2A 148(3) . . . . ? C14B C3B C4B C5B 169.6(11) . . . . ? C14B C3B C4B C30B -16.0(16) . . . . ? C4A C5A C21A O3A -115.8(19) . . . . ? C4A C3A C14A O2A -85.8(16) . . . . ? C30A C4A C5A C6 -173.4(13) . . . . ? C30A C4A C5A C21A 4(2) . . . . ? C30A C4A C3A C2 177.0(13) . . . . ? C30A C4A C3A C14A -2(2) . . . . ? C31B C30B C4B C3B 85.0(11) . . . . ? C31B C30B C4B C5B -100.6(12) . . . . ? C4B C3B C14B O2B -93.3(12) . . . . ? C22B O3B C21B C5B -165.7(15) . . . . ? Br3B C25B C26B C27B 179.5(9) . . . . ? Br3A C25A C26A C27A -177.4(11) . . . . ? Br3A C25A C24A C23A -179.9(12) . . . . ? C24B C25B C26B C27B -0.9(15) . . . . ? C26A C27A C22A C23A -9(3) . . . . ? C26A C27A C22A O3A 173.3(18) . . . . ? C26A C25A C24A C23A 1.8(19) . . . . ? C25B C24B C23B C22B 2.5(19) . . . . ? C25B C26B C27B C22B -2.9(18) . . . . ? C24A C23A C22A C27A 11(3) . . . . ? C24A C23A C22A O3A -170.6(18) . . . . ? C24A C25A C26A C27A 0.5(18) . . . . ? C23B C22B C27B C26B 6(2) . . . . ? C23B C24B C25B Br3B -179.3(9) . . . . ? C23B C24B C25B C26B 1.2(15) . . . . ? C27B C22B C23B C24B -6(2) . . . . ? C5A C6 C5B C21B 75(4) . . . . ? C5A C6 C5B C4B -96(4) . . . . ? C5A C4A C30A C31A 80.6(18) . . . . ? C5A C4A C3A C2 2(2) . . . . ? C5A C4A C3A C14A -176.4(15) . . . . ? C5A C21A O3A C22A 172.4(17) . . . . ? C3A C2 C1 C7 165.9(8) . . . . ? C3A C2 C1 C6 -8.8(10) . . . . ? C3A C2 C28 C29 101.1(9) . . . . ? C3A C2 C3B C14B -87(3) . . . . ? C3A C2 C3B C4B 83(3) . . . . ? C3A C4A C30A C31A -94.3(15) . . . . ? C3A C4A C5A C6 1(2) . . . . ? C3A C4A C5A C21A 178.5(14) . . . . ? C3A C14A O2A C15 -176.4(10) . . . . ? C21A O3A C22A C27A -11(3) . . . . ? C21A O3A C22A C23A 170.8(18) . . . . ? C22A C27A C26A C25A 3(2) . . . . ? C22A C23A C24A C25A -8(3) . . . . ? O2A C15 C20 C19 176.9(8) . . . . ? O2A C15 C16 C17 -176.6(6) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.029 0.500 0.000 379 73 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962433' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-ea-298K _audit_creation_date 2013-12-23 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-ea, 298 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Br3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Br3 O5' _chemical_formula_weight 805.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.8063(6) _cell_length_b 13.4053(12) _cell_length_c 15.0177(10) _cell_angle_alpha 110.995(8) _cell_angle_beta 92.706(5) _cell_angle_gamma 90.183(6) _cell_volume 1840.6(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3144 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.1421 _cell_measurement_theta_min 3.8191 _exptl_absorpt_coefficient_mu 3.326 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58617 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_unetI/netI 0.0970 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 24897 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.21 _diffrn_reflns_theta_min 3.83 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.866 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0438941000 _diffrn_orient_matrix_UB_12 0.0456664000 _diffrn_orient_matrix_UB_13 0.0190679000 _diffrn_orient_matrix_UB_21 0.0096709000 _diffrn_orient_matrix_UB_22 -0.0102055000 _diffrn_orient_matrix_UB_23 0.0430378000 _diffrn_orient_matrix_UB_31 0.0567953000 _diffrn_orient_matrix_UB_32 -0.0319973000 _diffrn_orient_matrix_UB_33 -0.0187187000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3895 _reflns_number_total 8657 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.870 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.080 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 391 _refine_ls_number_reflns 8657 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1510 _refine_ls_R_factor_gt 0.0623 _refine_ls_restrained_S_all 0.928 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0914P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1593 _refine_ls_wR_factor_ref 0.1906 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Others Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(Br3A)=Sof(C27A)=Sof(H27A)=Sof(C23A)=Sof(H23A)=Sof(C25A)= Sof(C26A)=Sof(H26A)=Sof(C24A)=Sof(H24A)=Sof(C5A)=Sof(C3A)=Sof(C21A)=Sof(H21C)= Sof(H21D)=Sof(O3A)=Sof(C22A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(O2A)=1-FVAR(1) Sof(O2B)=Sof(O3B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C22B)=Sof(Br3B)=Sof(C24B)=Sof(H24B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C23B)=Sof(H23B)=Sof(C27B)=Sof(H27B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C16(H16), C17(H17), C27A(H27A), C23A(H23A), C24B(H24B), C26A(H26A), C26B(H26B), C24A(H24A), C23B(H23B), C27B(H27B) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.98138(7) 0.11830(5) 0.96536(4) 0.0851(3) Uani 1 1 d . . . Br1 Br 1.71725(6) 0.04213(6) 0.12812(4) 0.0865(3) Uani 1 1 d . . . O2B O 0.9180(11) 0.2835(7) 0.6403(7) 0.059(3) Uiso 0.593(13) 1 d A 1 . C9 C 1.3113(5) 0.1107(4) 0.1794(3) 0.0523(12) Uani 1 1 d . . . H9 H 1.2273 0.0857 0.1476 0.063 Uiso 1 1 calc . . R O3B O 0.6911(11) 0.5354(9) 0.3673(9) 0.055(3) Uani 0.593(13) 1 d A 1 . C8 C 1.3178(4) 0.1923(4) 0.2681(3) 0.0476(11) Uani 1 1 d . . . C15 C 0.9339(5) 0.2426(3) 0.7148(3) 0.0532(12) Uani 1 1 d . . . C19 C 0.8438(5) 0.1520(4) 0.8083(4) 0.0640(14) Uani 1 1 d . . . H19 H 0.7723 0.1145 0.8215 0.077 Uiso 1 1 calc A . R C18 C 0.9625(5) 0.1721(4) 0.8642(4) 0.0568(13) Uani 1 1 d A . . C10 C 1.4304(5) 0.0673(4) 0.1391(4) 0.0623(14) Uani 1 1 d . . . H10 H 1.4268 0.0116 0.0802 0.075 Uiso 1 1 calc . . R C12 C 1.5610(5) 0.1856(4) 0.2716(4) 0.0630(14) Uani 1 1 d . . . H12 H 1.6451 0.2114 0.3029 0.076 Uiso 1 1 calc . . R C13 C 1.4434(5) 0.2281(4) 0.3125(4) 0.0609(13) Uani 1 1 d . . . H13 H 1.4482 0.2828 0.3721 0.073 Uiso 1 1 calc . . R C20 C 0.8302(5) 0.1866(4) 0.7334(4) 0.0601(13) Uani 1 1 d A . . H20 H 0.7500 0.1719 0.6950 0.072 Uiso 1 1 calc . . R C11 C 1.5550(4) 0.1056(4) 0.1852(3) 0.0521(12) Uani 1 1 d . . . C16 C 1.0539(6) 0.2654(4) 0.7728(4) 0.0651(14) Uani 1 1 d A . . H16 H 1.1239 0.3051 0.7609 0.078 Uiso 1 1 calc . . R O1 O 1.2061(3) 0.2403(2) 0.3167(2) 0.0575(9) Uani 1 1 d A . . C2 C 0.9430(4) 0.2268(3) 0.4202(3) 0.0476(11) Uani 1 1 d . . . C1 C 0.9750(4) 0.2656(3) 0.3493(3) 0.0464(11) Uani 1 1 d A . . C28 C 1.0001(5) 0.1229(3) 0.4220(4) 0.0576(13) Uani 1 1 d A . . H28A H 1.0154 0.1284 0.4879 0.069 Uiso 1 1 calc . . R H28B H 1.0877 0.1118 0.3929 0.069 Uiso 1 1 calc . . R C21B C 0.7907(11) 0.5337(7) 0.4352(7) 0.046(3) Uiso 0.593(13) 1 d A 1 . H21A H 0.7575 0.5686 0.4986 0.055 Uiso 0.593(13) 1 calc A 1 R H21B H 0.8713 0.5728 0.4299 0.055 Uiso 0.593(13) 1 calc A 1 R C7 C 1.0714(4) 0.2042(4) 0.2747(3) 0.0515(12) Uani 1 1 d . . . H7A H 1.0598 0.1280 0.2598 0.062 Uiso 1 1 calc A . R H7B H 1.0556 0.2194 0.2166 0.062 Uiso 1 1 calc . . R C32 C 0.9556(5) 0.4060(4) 0.2715(4) 0.0626(13) Uani 1 1 d A . . H32A H 1.0463 0.3849 0.2496 0.075 Uiso 1 1 calc . . R H32B H 0.9539 0.4834 0.2965 0.075 Uiso 1 1 calc . . R C6 C 0.9265(4) 0.3644(3) 0.3509(3) 0.0473(11) Uani 1 1 d . . . C33 C 0.8494(6) 0.3621(5) 0.1857(4) 0.0829(18) Uani 1 1 d . . . H33A H 0.8725 0.3880 0.1364 0.124 Uiso 1 1 calc A . GR H33B H 0.7601 0.3858 0.2065 0.124 Uiso 1 1 calc . . GR H33C H 0.8500 0.2854 0.1614 0.124 Uiso 1 1 calc . . GR C3B C 0.8385(14) 0.2784(10) 0.4861(9) 0.046(3) Uani 0.593(13) 1 d A 1 . C29 C 0.9070(6) 0.0262(4) 0.3698(5) 0.0791(17) Uani 1 1 d . . . H29A H 0.8994 0.0154 0.3030 0.119 Uiso 1 1 calc A . GR H29B H 0.8182 0.0383 0.3955 0.119 Uiso 1 1 calc . . GR H29C H 0.9448 -0.0361 0.3780 0.119 Uiso 1 1 calc . . GR C5B C 0.8275(14) 0.4206(9) 0.4219(8) 0.040(3) Uani 0.593(13) 1 d A 1 . C14B C 0.8079(14) 0.2408(9) 0.5636(9) 0.044(3) Uani 0.593(13) 1 d A 1 . H14A H 0.8052 0.1634 0.5405 0.053 Uiso 0.593(13) 1 calc A 1 R H14B H 0.7199 0.2665 0.5882 0.053 Uiso 0.593(13) 1 calc A 1 R C4A C 0.8413(17) 0.3949(15) 0.5039(12) 0.041(4) Uani 0.407(13) 1 d A 2 . C30A C 0.7649(13) 0.4659(10) 0.5906(10) 0.051(4) Uiso 0.407(13) 1 d A 2 . H30A H 0.7845 0.4435 0.6444 0.061 Uiso 0.407(13) 1 calc A 2 R H30B H 0.7957 0.5396 0.6084 0.061 Uiso 0.407(13) 1 calc A 2 R C30B C 0.6597(12) 0.4223(8) 0.5466(7) 0.064(3) Uani 0.593(13) 1 d A 1 . H30C H 0.6059 0.4648 0.5181 0.076 Uiso 0.593(13) 1 calc A 1 R H30D H 0.6014 0.3642 0.5477 0.076 Uiso 0.593(13) 1 calc A 1 R C31B C 0.7014(11) 0.4915(7) 0.6487(8) 0.077(4) Uani 0.593(13) 1 d A 1 . H31A H 0.7461 0.5557 0.6495 0.115 Uiso 0.593(13) 1 calc A 1 GR H31B H 0.7629 0.4531 0.6757 0.115 Uiso 0.593(13) 1 calc A 1 GR H31C H 0.6218 0.5097 0.6856 0.115 Uiso 0.593(13) 1 calc A 1 GR C17 C 1.0687(6) 0.2294(4) 0.8471(4) 0.0667(14) Uani 1 1 d . . . H17 H 1.1490 0.2433 0.8854 0.080 Uiso 1 1 calc A . R C4B C 0.7803(12) 0.3741(10) 0.4819(9) 0.044(3) Uani 0.593(13) 1 d A 1 . C31A C 0.614(2) 0.4573(17) 0.5665(15) 0.084(7) Uiso 0.407(13) 1 d A 2 . H31D H 0.5963 0.4718 0.5090 0.127 Uiso 0.407(13) 1 calc A 2 GR H31E H 0.5683 0.5082 0.6179 0.127 Uiso 0.407(13) 1 calc A 2 GR H31F H 0.5821 0.3865 0.5573 0.127 Uiso 0.407(13) 1 calc A 2 GR C22B C 0.6713(13) 0.6290(9) 0.3570(8) 0.044(4) Uiso 0.593(13) 1 d A 1 . Br3B Br 0.5255(9) 0.9439(6) 0.3233(8) 0.130(2) Uani 0.593(13) 1 d A 1 . Br3A Br 0.5065(13) 0.9589(8) 0.3520(9) 0.1023(19) Uani 0.407(13) 1 d A 2 . C27A C 0.6866(15) 0.7353(9) 0.4489(12) 0.049(4) Uiso 0.407(13) 1 d A 2 . H27A H 0.7319 0.7332 0.5040 0.059 Uiso 0.407(13) 1 calc A 2 R C23A C 0.5865(16) 0.6442(12) 0.2932(12) 0.046(5) Uiso 0.407(13) 1 d A 2 . H23A H 0.5657 0.5806 0.2427 0.055 Uiso 0.407(13) 1 calc A 2 R C24B C 0.5541(11) 0.7141(8) 0.2623(9) 0.070(4) Uiso 0.593(13) 1 d A 1 . H24B H 0.5041 0.7097 0.2067 0.084 Uiso 0.593(13) 1 calc A 1 R C25A C 0.5737(10) 0.8326(8) 0.3662(8) 0.029(3) Uiso 0.407(13) 1 d A 2 . C26A C 0.6437(12) 0.8308(10) 0.4460(11) 0.048(4) Uiso 0.407(13) 1 d A 2 . H26A H 0.6621 0.8937 0.4978 0.058 Uiso 0.407(13) 1 calc A 2 R C25B C 0.5821(9) 0.8099(8) 0.3296(8) 0.054(3) Uiso 0.593(13) 1 d A 1 . C26B C 0.6581(9) 0.8177(8) 0.4122(8) 0.055(3) Uiso 0.593(13) 1 d A 1 . H26B H 0.6771 0.8844 0.4590 0.066 Uiso 0.593(13) 1 calc A 1 R C24A C 0.5400(12) 0.7407(9) 0.2898(9) 0.038(3) Uiso 0.407(13) 1 d A 2 . H24A H 0.4877 0.7430 0.2373 0.045 Uiso 0.407(13) 1 calc A 2 R C23B C 0.5977(13) 0.6223(11) 0.2737(10) 0.070(4) Uiso 0.593(13) 1 d A 1 . H23B H 0.5784 0.5562 0.2261 0.084 Uiso 0.593(13) 1 calc A 1 R C27B C 0.7062(10) 0.7262(6) 0.4256(8) 0.045(3) Uiso 0.593(13) 1 d A 1 . H27B H 0.7604 0.7309 0.4795 0.054 Uiso 0.593(13) 1 calc A 1 R C5A C 0.8726(17) 0.4299(17) 0.4283(15) 0.044(6) Uiso 0.407(13) 1 d A 2 . C3A C 0.8787(17) 0.2925(16) 0.4983(14) 0.035(5) Uiso 0.407(13) 1 d A 2 . C21A C 0.8377(17) 0.5433(11) 0.4373(10) 0.047(4) Uiso 0.407(13) 1 d A 2 . H21C H 0.9184 0.5805 0.4290 0.057 Uiso 0.407(13) 1 calc A 2 R H21D H 0.8052 0.5819 0.5002 0.057 Uiso 0.407(13) 1 calc A 2 R O3A O 0.7275(16) 0.5385(16) 0.3609(14) 0.049(5) Uiso 0.407(13) 1 d A 2 . C22A C 0.6644(19) 0.6435(14) 0.3730(11) 0.049(7) Uiso 0.407(13) 1 d A 2 . C14A C 0.849(2) 0.2538(19) 0.5802(19) 0.053(7) Uiso 0.407(13) 1 d A 2 . H14C H 0.7670 0.2864 0.6104 0.064 Uiso 0.407(13) 1 calc A 2 R H14D H 0.8350 0.1768 0.5555 0.064 Uiso 0.407(13) 1 calc A 2 R O2A O 0.9529(13) 0.2801(10) 0.6426(9) 0.054(4) Uiso 0.407(13) 1 d A 2 . 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 Br2 0.1059(5) 0.1011(5) 0.0637(4) 0.0469(4) 0.0140(3) 0.0181(4) Br1 0.0570(4) 0.1191(6) 0.0762(4) 0.0247(4) 0.0146(3) 0.0179(3) C9 0.048(3) 0.058(3) 0.047(3) 0.014(3) 0.002(2) 0.002(2) O3B 0.045(6) 0.045(4) 0.084(6) 0.035(4) 0.000(5) 0.007(4) C8 0.046(3) 0.046(3) 0.051(3) 0.018(2) 0.003(2) 0.003(2) C15 0.072(3) 0.039(2) 0.054(3) 0.023(2) 0.013(3) 0.010(2) C19 0.061(3) 0.070(3) 0.077(4) 0.045(3) 0.021(3) 0.007(3) C18 0.065(3) 0.059(3) 0.051(3) 0.023(3) 0.017(3) 0.010(3) C10 0.064(3) 0.070(3) 0.050(3) 0.017(3) 0.009(3) 0.009(3) C12 0.048(3) 0.072(4) 0.065(4) 0.021(3) -0.003(3) -0.001(3) C13 0.051(3) 0.060(3) 0.055(3) 0.002(3) -0.005(2) -0.009(2) C20 0.053(3) 0.074(3) 0.072(4) 0.048(3) 0.009(3) 0.009(3) C11 0.042(3) 0.068(3) 0.048(3) 0.022(3) 0.001(2) 0.005(2) C16 0.076(4) 0.061(3) 0.065(4) 0.030(3) 0.013(3) -0.009(3) O1 0.0463(18) 0.057(2) 0.056(2) 0.0039(16) 0.0023(15) 0.0006(16) C2 0.049(3) 0.035(2) 0.057(3) 0.015(2) -0.003(2) 0.003(2) C1 0.045(2) 0.046(3) 0.047(3) 0.016(2) -0.002(2) -0.005(2) C28 0.056(3) 0.043(3) 0.077(4) 0.025(3) -0.002(3) 0.005(2) C7 0.047(3) 0.051(3) 0.050(3) 0.011(2) -0.001(2) 0.008(2) C32 0.065(3) 0.068(3) 0.064(3) 0.034(3) 0.005(3) 0.006(3) C6 0.054(3) 0.043(3) 0.048(3) 0.020(2) 0.001(2) 0.004(2) C33 0.082(4) 0.114(5) 0.053(3) 0.031(3) -0.007(3) 0.012(4) C3B 0.044(7) 0.042(6) 0.055(7) 0.021(5) -0.007(6) -0.008(5) C29 0.083(4) 0.050(3) 0.101(5) 0.023(3) 0.003(3) -0.005(3) C5B 0.036(6) 0.036(5) 0.054(6) 0.024(4) 0.000(5) 0.010(5) C14B 0.047(7) 0.038(6) 0.053(7) 0.024(5) -0.010(6) -0.007(5) C4A 0.039(9) 0.043(9) 0.037(8) 0.010(7) -0.007(7) 0.010(8) C30B 0.084(8) 0.044(5) 0.065(7) 0.021(5) 0.015(6) 0.022(6) C31B 0.091(7) 0.053(6) 0.078(8) 0.011(5) 0.021(6) -0.004(5) C17 0.068(3) 0.076(4) 0.055(3) 0.024(3) -0.004(3) -0.007(3) C4B 0.041(7) 0.041(6) 0.050(7) 0.016(5) -0.002(5) 0.010(6) Br3B 0.071(2) 0.115(4) 0.263(7) 0.147(4) -0.036(3) -0.008(2) Br3A 0.077(3) 0.0689(18) 0.178(4) 0.068(2) -0.017(2) 0.0117(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br2 C18 1.903(5) . ? Br1 C11 1.899(4) . ? O2B C15 1.415(10) . ? O2B C14B 1.491(17) . ? C9 H9 0.9300 . ? C9 C8 1.386(6) . ? C9 C10 1.374(6) . ? O3B C21B 1.385(15) . ? O3B C22B 1.331(16) . ? C8 C13 1.372(6) . ? C8 O1 1.375(5) . ? C15 C20 1.359(7) . ? C15 C16 1.395(7) . ? C15 O2A 1.368(13) . ? C19 H19 0.9300 . ? C19 C18 1.369(7) . ? C19 C20 1.365(6) . ? C18 C17 1.379(7) . ? C10 H10 0.9300 . ? C10 C11 1.377(7) . ? C12 H12 0.9300 . ? C12 C13 1.362(6) . ? C12 C11 1.354(7) . ? C13 H13 0.9300 . ? C20 H20 0.9300 . ? C16 H16 0.9300 . ? C16 C17 1.368(7) . ? O1 C7 1.440(5) . ? C2 C1 1.390(6) . ? C2 C28 1.511(6) . ? C2 C3B 1.455(14) . ? C2 C3A 1.37(2) . ? C1 C7 1.507(6) . ? C1 C6 1.401(6) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C29 1.525(7) . ? C21B H21A 0.9700 . ? C21B H21B 0.9700 . ? C21B C5B 1.504(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C6 1.523(6) . ? C32 C33 1.555(7) . ? C6 C5B 1.474(12) . ? C6 C5A 1.32(2) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C3B C14B 1.467(16) . ? C3B C4B 1.427(17) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C5B C4B 1.362(17) . ? C14B H14A 0.9700 . ? C14B H14B 0.9700 . ? C4A C30A 1.54(2) . ? C4A C5A 1.42(3) . ? C4A C3A 1.40(3) . ? C30A H30A 0.9700 . ? C30A H30B 0.9700 . ? C30A C31A 1.50(2) . ? C30B H30C 0.9700 . ? C30B H30D 0.9700 . ? C30B C31B 1.515(16) . ? C30B C4B 1.557(17) . ? C31B H31A 0.9600 . ? C31B H31B 0.9600 . ? C31B H31C 0.9600 . ? C17 H17 0.9300 . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? C22B C23B 1.389(11) . ? C22B C27B 1.370(11) . ? Br3B C25B 1.914(11) . ? Br3A C25A 1.897(14) . ? C27A H27A 0.9300 . ? C27A C26A 1.363(12) . ? C27A C22A 1.353(13) . ? C23A H23A 0.9300 . ? C23A C24A 1.390(12) . ? C23A C22A 1.393(13) . ? C24B H24B 0.9300 . ? C24B C25B 1.338(11) . ? C24B C23B 1.368(11) . ? C25A C26A 1.362(12) . ? C25A C24A 1.375(12) . ? C26A H26A 0.9300 . ? C25B C26B 1.389(10) . ? C26B H26B 0.9300 . ? C26B C27B 1.392(9) . ? C24A H24A 0.9300 . ? C23B H23B 0.9300 . ? C27B H27B 0.9300 . ? C5A C21A 1.52(3) . ? C3A C14A 1.54(3) . ? C21A H21C 0.9700 . ? C21A H21D 0.9700 . ? C21A O3A 1.52(2) . ? O3A C22A 1.49(3) . ? C14A H14C 0.9700 . ? C14A H14D 0.9700 . ? C14A O2A 1.31(3) . ? 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 C15 O2B C14B 120.7(7) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C10 C9 C8 119.2(5) . . ? C22B O3B C21B 116.5(10) . . ? C13 C8 C9 118.9(4) . . ? C13 C8 O1 116.5(4) . . ? O1 C8 C9 124.7(4) . . ? C20 C15 O2B 120.3(6) . . ? C20 C15 C16 120.1(5) . . ? C20 C15 O2A 132.8(7) . . ? C16 C15 O2B 119.5(6) . . ? O2A C15 O2B 14.2(7) . . ? O2A C15 C16 107.0(7) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C20 C19 C18 120.2(5) . . ? C19 C18 Br2 119.4(4) . . ? C19 C18 C17 120.8(5) . . ? C17 C18 Br2 119.8(4) . . ? C9 C10 H10 119.7 . . ? C9 C10 C11 120.5(5) . . ? C11 C10 H10 119.7 . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C11 C12 C13 119.6(5) . . ? C8 C13 H13 119.2 . . ? C12 C13 C8 121.6(5) . . ? C12 C13 H13 119.2 . . ? C15 C20 C19 120.0(5) . . ? C15 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C10 C11 Br1 119.3(4) . . ? C12 C11 Br1 120.5(4) . . ? C12 C11 C10 120.1(4) . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.1(5) . . ? C17 C16 H16 120.0 . . ? C8 O1 C7 119.0(3) . . ? C1 C2 C28 121.2(4) . . ? C1 C2 C3B 119.7(6) . . ? C3B C2 C28 118.6(6) . . ? C3A C2 C1 118.8(9) . . ? C3A C2 C28 119.1(9) . . ? C3A C2 C3B 17.5(9) . . ? C2 C1 C7 119.1(4) . . ? C2 C1 C6 120.6(4) . . ? C6 C1 C7 120.1(4) . . ? C2 C28 H28A 108.9 . . ? C2 C28 H28B 108.9 . . ? C2 C28 C29 113.4(4) . . ? H28A C28 H28B 107.7 . . ? C29 C28 H28A 108.9 . . ? C29 C28 H28B 108.9 . . ? O3B C21B H21A 109.5 . . ? O3B C21B H21B 109.5 . . ? O3B C21B C5B 110.6(9) . . ? H21A C21B H21B 108.1 . . ? C5B C21B H21A 109.5 . . ? C5B C21B H21B 109.5 . . ? O1 C7 C1 105.2(3) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.9 . . ? C6 C32 H32A 109.3 . . ? C6 C32 H32B 109.3 . . ? C6 C32 C33 111.8(4) . . ? C33 C32 H32A 109.3 . . ? C33 C32 H32B 109.3 . . ? C1 C6 C32 121.2(4) . . ? C1 C6 C5B 119.0(5) . . ? C5B C6 C32 119.0(5) . . ? C5A C6 C1 119.7(10) . . ? C5A C6 C32 118.3(10) . . ? C5A C6 C5B 17.6(10) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 120.1(10) . . ? C4B C3B C2 118.8(10) . . ? C4B C3B C14B 120.5(11) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 119.9(9) . . ? C4B C5B C21B 119.9(10) . . ? C4B C5B C6 119.9(9) . . ? O2B C14B H14A 110.2 . . ? O2B C14B H14B 110.2 . . ? C3B C14B O2B 107.5(10) . . ? C3B C14B H14A 110.2 . . ? C3B C14B H14B 110.2 . . ? H14A C14B H14B 108.5 . . ? C5A C4A C30A 121.8(15) . . ? C3A C4A C30A 119.3(15) . . ? C3A C4A C5A 118.9(16) . . ? C4A C30A H30A 109.7 . . ? C4A C30A H30B 109.7 . . ? H30A C30A H30B 108.2 . . ? C31A C30A C4A 109.9(15) . . ? C31A C30A H30A 109.7 . . ? C31A C30A H30B 109.7 . . ? H30C C30B H30D 107.5 . . ? C31B C30B H30C 108.5 . . ? C31B C30B H30D 108.5 . . ? C31B C30B C4B 115.0(11) . . ? C4B C30B H30C 108.5 . . ? C4B C30B H30D 108.5 . . ? C18 C17 H17 120.6 . . ? C16 C17 C18 118.8(5) . . ? C16 C17 H17 120.6 . . ? C3B C4B C30B 117.9(10) . . ? C5B C4B C3B 120.8(11) . . ? C5B C4B C30B 121.2(10) . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? O3B C22B C23B 114.4(10) . . ? O3B C22B C27B 124.3(11) . . ? C27B C22B C23B 120.9(11) . . ? C26A C27A H27A 119.4 . . ? C22A C27A H27A 119.4 . . ? C22A C27A C26A 121.2(14) . . ? C24A C23A H23A 120.2 . . ? C24A C23A C22A 119.5(15) . . ? C22A C23A H23A 120.2 . . ? C25B C24B H24B 119.4 . . ? C25B C24B C23B 121.1(11) . . ? C23B C24B H24B 119.4 . . ? C26A C25A Br3A 123.8(9) . . ? C26A C25A C24A 122.1(10) . . ? C24A C25A Br3A 114.0(8) . . ? C27A C26A H26A 120.5 . . ? C25A C26A C27A 119.0(12) . . ? C25A C26A H26A 120.5 . . ? C24B C25B Br3B 125.4(8) . . ? C24B C25B C26B 120.0(9) . . ? C26B C25B Br3B 114.6(7) . . ? C25B C26B H26B 119.8 . . ? C25B C26B C27B 120.4(9) . . ? C27B C26B H26B 119.8 . . ? C23A C24A H24A 120.9 . . ? C25A C24A C23A 118.1(11) . . ? C25A C24A H24A 120.9 . . ? C22B C23B H23B 120.3 . . ? C24B C23B C22B 119.3(12) . . ? C24B C23B H23B 120.3 . . ? C22B C27B C26B 118.1(9) . . ? C22B C27B H27B 121.0 . . ? C26B C27B H27B 121.0 . . ? C6 C5A C4A 120.7(17) . . ? C6 C5A C21A 120.7(16) . . ? C4A C5A C21A 118.5(16) . . ? C2 C3A C4A 120.2(16) . . ? C2 C3A C14A 119.9(16) . . ? C4A C3A C14A 119.9(17) . . ? C5A C21A H21C 110.0 . . ? C5A C21A H21D 110.0 . . ? C5A C21A O3A 108.6(14) . . ? H21C C21A H21D 108.4 . . ? O3A C21A H21C 110.0 . . ? O3A C21A H21D 110.0 . . ? C22A O3A C21A 114.2(14) . . ? C27A C22A C23A 119.9(16) . . ? C27A C22A O3A 125.8(14) . . ? C23A C22A O3A 114.1(13) . . ? C3A C14A H14C 109.9 . . ? C3A C14A H14D 109.9 . . ? H14C C14A H14D 108.3 . . ? O2A C14A C3A 108.9(15) . . ? O2A C14A H14C 109.9 . . ? O2A C14A H14D 109.9 . . ? C14A O2A C15 110.9(13) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 178.7(4) . . . . ? O2B C15 C20 C19 -176.8(6) . . . . ? O2B C15 C16 C17 177.8(6) . . . . ? O2B C15 O2A C14A -33(3) . . . . ? C9 C8 C13 C12 0.0(8) . . . . ? C9 C8 O1 C7 0.6(6) . . . . ? C9 C10 C11 Br1 179.0(4) . . . . ? C9 C10 C11 C12 1.0(8) . . . . ? O3B C21B C5B C6 82.8(13) . . . . ? O3B C21B C5B C4B -104.0(13) . . . . ? O3B C22B C23B C24B 170.5(12) . . . . ? O3B C22B C27B C26B -168.8(12) . . . . ? C8 C9 C10 C11 -1.3(7) . . . . ? C8 O1 C7 C1 175.1(4) . . . . ? C15 O2B C14B C3B -166.1(9) . . . . ? C15 C16 C17 C18 -1.0(8) . . . . ? C19 C18 C17 C16 -0.4(8) . . . . ? C18 C19 C20 C15 -1.0(8) . . . . ? C10 C9 C8 C13 0.8(7) . . . . ? C10 C9 C8 O1 -178.4(4) . . . . ? C13 C8 O1 C7 -178.5(4) . . . . ? C13 C12 C11 Br1 -178.2(4) . . . . ? C13 C12 C11 C10 -0.2(8) . . . . ? C20 C15 C16 C17 1.4(7) . . . . ? C20 C15 O2A C14A -1.0(18) . . . . ? C20 C19 C18 Br2 -177.7(4) . . . . ? C20 C19 C18 C17 1.4(8) . . . . ? C11 C12 C13 C8 -0.3(8) . . . . ? C16 C15 C20 C19 -0.4(7) . . . . ? C16 C15 O2A C14A 174.6(13) . . . . ? O1 C8 C13 C12 179.2(4) . . . . ? C2 C1 C7 O1 -85.3(5) . . . . ? C2 C1 C6 C32 -177.4(4) . . . . ? C2 C1 C6 C5B -7.4(9) . . . . ? C2 C1 C6 C5A 12.8(11) . . . . ? C2 C3B C14B O2B 77.7(12) . . . . ? C2 C3B C4B C5B -4.3(17) . . . . ? C2 C3B C4B C30B 174.6(10) . . . . ? C2 C3A C14A O2A 90(2) . . . . ? C1 C2 C28 C29 -92.5(5) . . . . ? C1 C2 C3B C14B -177.4(9) . . . . ? C1 C2 C3B C4B -5.8(13) . . . . ? C1 C2 C3A C4A 2.7(17) . . . . ? C1 C2 C3A C14A -176.7(12) . . . . ? C1 C6 C5B C21B 170.5(8) . . . . ? C1 C6 C5B C4B -2.8(14) . . . . ? C1 C6 C5A C4A -10.9(18) . . . . ? C1 C6 C5A C21A 171.3(10) . . . . ? C28 C2 C1 C7 -1.7(6) . . . . ? C28 C2 C1 C6 -177.1(4) . . . . ? C28 C2 C3B C14B 11.0(14) . . . . ? C28 C2 C3B C4B -177.4(8) . . . . ? C28 C2 C3A C4A 171.5(11) . . . . ? C28 C2 C3A C14A -7.9(18) . . . . ? C21B O3B C22B C23B 164.4(11) . . . . ? C21B O3B C22B C27B -22(2) . . . . ? C21B C5B C4B C3B -164.8(11) . . . . ? C21B C5B C4B C30B 16.3(18) . . . . ? C7 C1 C6 C32 7.3(7) . . . . ? C7 C1 C6 C5B 177.3(7) . . . . ? C7 C1 C6 C5A -162.5(10) . . . . ? C32 C6 C5B C21B -19.3(13) . . . . ? C32 C6 C5B C4B 167.4(9) . . . . ? C32 C6 C5A C4A 179.0(11) . . . . ? C32 C6 C5A C21A 1.2(18) . . . . ? C6 C1 C7 O1 90.1(5) . . . . ? C6 C5B C4B C3B 8.5(18) . . . . ? C6 C5B C4B C30B -170.4(10) . . . . ? C6 C5A C21A O3A 63.7(18) . . . . ? C33 C32 C6 C1 85.3(6) . . . . ? C33 C32 C6 C5B -84.6(8) . . . . ? C33 C32 C6 C5A -104.7(10) . . . . ? C3B C2 C1 C7 -173.1(7) . . . . ? C3B C2 C1 C6 11.6(9) . . . . ? C3B C2 C28 C29 79.0(8) . . . . ? C3B C2 C3A C4A -95(4) . . . . ? C3B C2 C3A C14A 86(4) . . . . ? C5B C6 C5A C4A 82(4) . . . . ? C5B C6 C5A C21A -96(4) . . . . ? C14B O2B C15 C20 -18.0(10) . . . . ? C14B O2B C15 C16 165.6(7) . . . . ? C14B O2B C15 O2A 136(4) . . . . ? C14B C3B C4B C5B 167.3(12) . . . . ? C14B C3B C4B C30B -13.8(17) . . . . ? C4A C5A C21A O3A -114.2(16) . . . . ? C4A C3A C14A O2A -89.2(19) . . . . ? C30A C4A C5A C6 -173.6(14) . . . . ? C30A C4A C5A C21A 4(2) . . . . ? C30A C4A C3A C2 177.9(13) . . . . ? C30A C4A C3A C14A -3(2) . . . . ? C31B C30B C4B C3B 83.1(12) . . . . ? C31B C30B C4B C5B -98.0(13) . . . . ? C4B C3B C14B O2B -93.8(13) . . . . ? C22B O3B C21B C5B -165.3(11) . . . . ? Br3B C25B C26B C27B -179.7(8) . . . . ? Br3A C25A C26A C27A 179.6(11) . . . . ? Br3A C25A C24A C23A 179.1(10) . . . . ? C24B C25B C26B C27B 0.3(15) . . . . ? C26A C27A C22A C23A -6(3) . . . . ? C26A C27A C22A O3A 168.3(16) . . . . ? C26A C25A C24A C23A -3.7(18) . . . . ? C25B C24B C23B C22B 0.6(18) . . . . ? C25B C26B C27B C22B -2.8(15) . . . . ? C24A C23A C22A C27A 4(3) . . . . ? C24A C23A C22A O3A -170.1(14) . . . . ? C24A C25A C26A C27A 2.7(19) . . . . ? C23B C22B C27B C26B 4.2(18) . . . . ? C23B C24B C25B Br3B -179.2(9) . . . . ? C23B C24B C25B C26B 0.8(16) . . . . ? C27B C22B C23B C24B -3(2) . . . . ? C5A C6 C5B C21B 73(4) . . . . ? C5A C6 C5B C4B -100(4) . . . . ? C5A C4A C30A C31A 82.3(18) . . . . ? C5A C4A C3A C2 -1(2) . . . . ? C5A C4A C3A C14A 178.5(15) . . . . ? C5A C21A O3A C22A 168.9(15) . . . . ? C3A C2 C1 C7 166.8(9) . . . . ? C3A C2 C1 C6 -8.6(10) . . . . ? C3A C2 C28 C29 99.0(10) . . . . ? C3A C2 C3B C14B -85(4) . . . . ? C3A C2 C3B C4B 86(4) . . . . ? C3A C4A C30A C31A -96.4(16) . . . . ? C3A C4A C5A C6 5(2) . . . . ? C3A C4A C5A C21A -177.1(14) . . . . ? C3A C14A O2A C15 -177.1(13) . . . . ? C21A O3A C22A C27A -7(3) . . . . ? C21A O3A C22A C23A 166.6(15) . . . . ? C22A C27A C26A C25A 2(2) . . . . ? C22A C23A C24A C25A 0(2) . . . . ? O2A C15 C20 C19 174.6(8) . . . . ? O2A C15 C16 C17 -174.8(7) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.027 0.500 0.000 396 45 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962434' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-ea-118K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-ea, 118 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 I3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 I3 O5' _chemical_formula_weight 946.40 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.8275(5) _cell_length_b 13.2269(8) _cell_length_c 15.4915(8) _cell_angle_alpha 111.605(5) _cell_angle_beta 94.919(4) _cell_angle_gamma 91.912(5) _cell_volume 1860.74(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6336 _cell_measurement_temperature 118(2) _cell_measurement_theta_max 29.2004 _cell_measurement_theta_min 3.4692 _exptl_absorpt_coefficient_mu 2.559 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.44595 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 924 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_unetI/netI 0.0484 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 20489 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.26 _diffrn_reflns_theta_min 3.48 _diffrn_ambient_temperature 118(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.846 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0641054000 _diffrn_orient_matrix_UB_12 0.0051306000 _diffrn_orient_matrix_UB_13 0.0184978000 _diffrn_orient_matrix_UB_21 0.0329336000 _diffrn_orient_matrix_UB_22 0.0319144000 _diffrn_orient_matrix_UB_23 0.0449184000 _diffrn_orient_matrix_UB_31 -0.0089239000 _diffrn_orient_matrix_UB_32 0.0479404000 _diffrn_orient_matrix_UB_33 -0.0096253000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6408 _reflns_number_total 8591 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.223 _refine_diff_density_min -1.106 _refine_diff_density_rms 0.129 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 421 _refine_ls_number_reflns 8591 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0460 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.4502P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1205 _refine_ls_wR_factor_ref 0.1313 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 3. Others Sof(O2A)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(O3A)=Sof(C22A)= Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(C24A)=Sof(H24A)= Sof(C23A)=Sof(H23A)=Sof(I3A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1) Sof(I3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C24B)=Sof(H24B)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I2 I 1.00456(3) 0.14243(3) 0.97846(2) 0.04059(11) Uani 1 1 d . . . I1 I 1.70757(3) 0.03403(3) 0.12788(2) 0.04244(11) Uani 1 1 d . . . I3B I 0.5073(6) 0.9546(5) 0.3301(5) 0.0751(13) Uani 0.520(10) 1 d A 1 . O2A O 0.967(2) 0.292(2) 0.6458(18) 0.029(3) Uani 0.480(10) 1 d A 2 . C9 C 1.2896(5) 0.1104(4) 0.1861(3) 0.0318(10) Uani 1 1 d . . . H9 H 1.2006 0.0818 0.1561 0.038 Uiso 1 1 calc . . R O3B O 0.6793(10) 0.5262(10) 0.3605(8) 0.029(3) Uiso 0.520(10) 1 d A 1 . C8 C 1.3054(4) 0.1956(3) 0.2706(3) 0.0277(9) Uani 1 1 d . . . C15 C 0.9543(5) 0.2523(4) 0.7116(3) 0.0350(11) Uani 1 1 d . . . C19 C 0.8605(5) 0.1659(4) 0.8072(3) 0.0338(10) Uani 1 1 d . . . H19 H 0.7868 0.1275 0.8205 0.041 Uiso 1 1 calc A . R C18 C 0.9828(5) 0.1924(4) 0.8648(3) 0.0311(10) Uani 1 1 d A . . C10 C 1.4061(5) 0.0658(4) 0.1442(3) 0.0347(10) Uani 1 1 d . . . H10 H 1.3964 0.0065 0.0856 0.042 Uiso 1 1 calc . . R C12 C 1.5499(5) 0.1967(4) 0.2733(3) 0.0337(10) Uani 1 1 d . . . H12 H 1.6385 0.2275 0.3026 0.040 Uiso 1 1 calc . . R C13 C 1.4362(5) 0.2381(4) 0.3135(3) 0.0332(10) Uani 1 1 d . . . H13 H 1.4461 0.2973 0.3720 0.040 Uiso 1 1 calc . . R C20 C 0.8460(5) 0.1957(4) 0.7302(3) 0.0374(11) Uani 1 1 d A . . H20 H 0.7625 0.1775 0.6904 0.045 Uiso 1 1 calc . . R C22B C 0.6508(15) 0.6233(11) 0.3571(9) 0.035(4) Uiso 0.520(10) 1 d A 1 . C27B C 0.6976(13) 0.7210(8) 0.4273(9) 0.032(3) Uiso 0.520(10) 1 d A 1 . H27B H 0.7567 0.7240 0.4801 0.038 Uiso 0.520(10) 1 calc A 1 R C23B C 0.5697(16) 0.6127(13) 0.2769(10) 0.048(4) Uiso 0.520(10) 1 d A 1 . H23B H 0.5433 0.5431 0.2298 0.057 Uiso 0.520(10) 1 calc A 1 R C11 C 1.5348(5) 0.1083(4) 0.1883(3) 0.0324(10) Uani 1 1 d . . . C16 C 1.0746(6) 0.2796(4) 0.7692(4) 0.0400(11) Uani 1 1 d A . . H16 H 1.1470 0.3196 0.7564 0.048 Uiso 1 1 calc . . R C25B C 0.5677(9) 0.8046(9) 0.3368(8) 0.028(2) Uiso 0.520(10) 1 d A 1 . C26B C 0.6532(10) 0.8153(9) 0.4164(8) 0.035(3) Uiso 0.520(10) 1 d A 1 . H26B H 0.6810 0.8852 0.4624 0.042 Uiso 0.520(10) 1 calc A 1 R O1 O 1.1983(3) 0.2446(2) 0.3191(2) 0.0324(7) Uani 1 1 d A . . C2 C 0.9441(5) 0.2230(4) 0.4200(3) 0.0333(10) Uani 1 1 d . . . C1 C 0.9682(5) 0.2642(4) 0.3503(3) 0.0297(9) Uani 1 1 d A . . C28 C 1.0078(5) 0.1201(4) 0.4220(3) 0.0331(10) Uani 1 1 d A . . H28A H 1.0301 0.1277 0.4878 0.040 Uiso 1 1 calc . . R H28B H 1.0944 0.1123 0.3926 0.040 Uiso 1 1 calc . . R C21B C 0.7756(13) 0.5299(12) 0.4379(10) 0.032(3) Uani 0.520(10) 1 d A 1 . H21A H 0.7336 0.5608 0.4972 0.038 Uiso 0.520(10) 1 calc A 1 R H21B H 0.8583 0.5768 0.4419 0.038 Uiso 0.520(10) 1 calc A 1 R C7 C 1.0605(4) 0.2050(4) 0.2777(3) 0.0289(9) Uani 1 1 d . . . H7A H 1.0477 0.1253 0.2614 0.035 Uiso 1 1 calc A . R H7B H 1.0402 0.2206 0.2203 0.035 Uiso 1 1 calc . . R C32 C 0.9444(5) 0.4077(4) 0.2770(3) 0.0318(10) Uani 1 1 d A . . H32A H 0.9475 0.4883 0.3037 0.038 Uiso 1 1 calc . . R H32B H 1.0347 0.3863 0.2551 0.038 Uiso 1 1 calc . . R C6 C 0.9182(5) 0.3638(4) 0.3533(3) 0.0342(10) Uani 1 1 d . . . C33 C 0.8347(5) 0.3651(4) 0.1942(3) 0.0373(11) Uani 1 1 d . . . H33A H 0.8532 0.3979 0.1487 0.056 Uiso 1 1 calc A . GR H33B H 0.7448 0.3844 0.2158 0.056 Uiso 1 1 calc . . GR H33C H 0.8355 0.2857 0.1649 0.056 Uiso 1 1 calc . . GR C3B C 0.8346(11) 0.2711(7) 0.4830(6) 0.0231(19) Uani 0.520(10) 1 d A 1 . C29 C 0.9133(5) 0.0172(4) 0.3712(4) 0.0397(11) Uani 1 1 d . . . H29A H 0.9000 0.0041 0.3045 0.060 Uiso 1 1 calc A . GR H29B H 0.8246 0.0266 0.3967 0.060 Uiso 1 1 calc . . GR H29C H 0.9547 -0.0452 0.3800 0.060 Uiso 1 1 calc . . GR C5B C 0.8141(12) 0.4159(12) 0.4228(10) 0.024(3) Uani 0.520(10) 1 d A 1 . C14B C 0.8130(13) 0.2309(9) 0.5596(7) 0.025(2) Uani 0.520(10) 1 d A 1 . H14A H 0.7275 0.2566 0.5874 0.030 Uiso 0.520(10) 1 calc A 1 R H14B H 0.8078 0.1502 0.5358 0.030 Uiso 0.520(10) 1 calc A 1 R C4A C 0.8456(12) 0.3899(9) 0.4997(6) 0.024(2) Uani 0.480(10) 1 d A 2 . C30A C 0.7725(8) 0.4558(7) 0.5822(6) 0.022(2) Uani 0.480(10) 1 d A 2 . H30A H 0.7939 0.4305 0.6342 0.027 Uiso 0.480(10) 1 calc A 2 R H30B H 0.8054 0.5336 0.6037 0.027 Uiso 0.480(10) 1 calc A 2 R C30B C 0.6583(10) 0.4089(8) 0.5420(6) 0.027(2) Uani 0.520(10) 1 d A 1 . H30C H 0.6010 0.3463 0.5429 0.032 Uiso 0.520(10) 1 calc A 1 R H30D H 0.6003 0.4490 0.5120 0.032 Uiso 0.520(10) 1 calc A 1 R C31B C 0.7047(10) 0.4845(8) 0.6430(6) 0.035(2) Uani 0.520(10) 1 d A 1 . H31A H 0.7553 0.5497 0.6432 0.052 Uiso 0.520(10) 1 calc A 1 GR H31B H 0.7641 0.4462 0.6731 0.052 Uiso 0.520(10) 1 calc A 1 GR H31C H 0.6243 0.5058 0.6772 0.052 Uiso 0.520(10) 1 calc A 1 GR C17 C 1.0915(5) 0.2495(4) 0.8462(3) 0.0370(11) Uani 1 1 d . . . H17 H 1.1755 0.2674 0.8855 0.044 Uiso 1 1 calc A . R C4B C 0.7738(11) 0.3656(7) 0.4832(6) 0.0216(19) Uani 0.520(10) 1 d A 1 . C24B C 0.5288(13) 0.7057(9) 0.2675(9) 0.042(3) Uiso 0.520(10) 1 d A 1 . H24B H 0.4734 0.7020 0.2130 0.051 Uiso 0.520(10) 1 calc A 1 R C31A C 0.6222(12) 0.4446(11) 0.5568(8) 0.033(3) Uiso 0.480(10) 1 d A 2 . H31D H 0.6004 0.4748 0.5086 0.050 Uiso 0.480(10) 1 calc A 2 GR H31E H 0.5766 0.4841 0.6121 0.050 Uiso 0.480(10) 1 calc A 2 GR H31F H 0.5902 0.3673 0.5327 0.050 Uiso 0.480(10) 1 calc A 2 GR C3A C 0.8891(11) 0.2875(9) 0.4945(7) 0.018(2) Uiso 0.480(10) 1 d A 2 . C5A C 0.8701(13) 0.4256(12) 0.4270(11) 0.021(3) Uani 0.480(10) 1 d A 2 . C21A C 0.8296(13) 0.5418(10) 0.4376(8) 0.014(2) Uani 0.480(10) 1 d A 2 . H21C H 0.8029 0.5803 0.5011 0.017 Uiso 0.480(10) 1 calc A 2 R H21D H 0.9089 0.5840 0.4290 0.017 Uiso 0.480(10) 1 calc A 2 R O3A O 0.7179(13) 0.5343(9) 0.3697(7) 0.029(2) Uani 0.480(10) 1 d A 2 . C22A C 0.6674(14) 0.6357(11) 0.3729(8) 0.025(3) Uiso 0.480(10) 1 d A 2 . C27A C 0.6963(14) 0.7352(9) 0.4482(10) 0.030(4) Uiso 0.480(10) 1 d A 2 . H27A H 0.7491 0.7360 0.5028 0.036 Uiso 0.480(10) 1 calc A 2 R C26A C 0.6507(10) 0.8333(9) 0.4462(8) 0.027(2) Uiso 0.480(10) 1 d A 2 . H26A H 0.6743 0.8996 0.4979 0.032 Uiso 0.480(10) 1 calc A 2 R C25A C 0.5718(9) 0.8326(8) 0.3691(7) 0.019(2) Uiso 0.480(10) 1 d A 2 . C24A C 0.5363(10) 0.7355(9) 0.2916(8) 0.022(2) Uiso 0.480(10) 1 d A 2 . H24A H 0.4831 0.7367 0.2378 0.027 Uiso 0.480(10) 1 calc A 2 R C23A C 0.5807(13) 0.6359(10) 0.2943(9) 0.027(3) Uiso 0.480(10) 1 d A 2 . H23A H 0.5527 0.5692 0.2439 0.032 Uiso 0.480(10) 1 calc A 2 R I3A I 0.5060(7) 0.9779(5) 0.3567(4) 0.0583(7) Uani 0.480(10) 1 d A 2 . C14A C 0.8603(15) 0.2461(12) 0.5707(12) 0.028(4) Uiso 0.480(10) 1 d A 2 . H14C H 0.7702 0.2682 0.5927 0.034 Uiso 0.480(10) 1 calc A 2 R H14D H 0.8586 0.1655 0.5466 0.034 Uiso 0.480(10) 1 calc A 2 R O2B O 0.931(2) 0.276(2) 0.6276(15) 0.030(3) Uani 0.520(10) 1 d A 1 . 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 I2 0.0491(2) 0.0494(2) 0.03206(18) 0.02351(16) 0.00996(14) 0.01101(16) I1 0.03656(19) 0.0486(2) 0.0394(2) 0.01335(16) 0.00222(14) 0.00578(15) I3B 0.0363(7) 0.069(2) 0.159(4) 0.089(2) -0.002(2) 0.0075(14) O2A 0.040(10) 0.025(8) 0.020(8) 0.009(6) -0.010(6) -0.011(6) C9 0.032(2) 0.030(3) 0.033(2) 0.013(2) -0.0039(19) 0.004(2) C8 0.033(2) 0.021(2) 0.030(2) 0.0113(18) -0.0033(18) 0.0021(18) C15 0.059(3) 0.022(2) 0.033(2) 0.017(2) 0.017(2) 0.013(2) C19 0.033(2) 0.036(3) 0.041(3) 0.022(2) 0.012(2) 0.008(2) C18 0.038(2) 0.033(3) 0.026(2) 0.0132(19) 0.0098(18) 0.009(2) C10 0.045(3) 0.026(2) 0.030(2) 0.0085(19) -0.007(2) 0.004(2) C12 0.028(2) 0.033(3) 0.039(3) 0.015(2) -0.0057(19) -0.0059(19) C13 0.040(3) 0.025(2) 0.028(2) 0.0064(19) -0.0096(19) -0.007(2) C20 0.047(3) 0.037(3) 0.036(3) 0.022(2) 0.008(2) 0.007(2) C11 0.033(2) 0.034(3) 0.033(2) 0.016(2) 0.0051(19) 0.008(2) C16 0.051(3) 0.033(3) 0.040(3) 0.016(2) 0.019(2) 0.001(2) O1 0.0325(17) 0.0256(17) 0.0331(17) 0.0064(14) -0.0055(13) -0.0035(13) C2 0.050(3) 0.024(2) 0.029(2) 0.0123(19) 0.002(2) 0.009(2) C1 0.040(2) 0.023(2) 0.025(2) 0.0077(18) -0.0026(18) 0.0028(19) C28 0.044(3) 0.023(2) 0.033(2) 0.0121(19) 0.001(2) 0.007(2) C21B 0.019(6) 0.034(6) 0.053(7) 0.029(5) 0.005(6) -0.006(5) C7 0.032(2) 0.024(2) 0.029(2) 0.0101(18) -0.0051(18) -0.0030(18) C32 0.035(2) 0.030(3) 0.034(2) 0.017(2) 0.0018(19) 0.001(2) C6 0.052(3) 0.027(2) 0.024(2) 0.0120(19) -0.005(2) 0.002(2) C33 0.037(3) 0.051(3) 0.027(2) 0.019(2) 0.0030(19) 0.004(2) C3B 0.019(5) 0.026(5) 0.028(5) 0.015(4) -0.001(4) -0.005(4) C29 0.046(3) 0.023(2) 0.050(3) 0.015(2) 0.000(2) 0.005(2) C5B 0.018(6) 0.029(6) 0.029(5) 0.011(4) 0.014(6) 0.009(6) C14B 0.023(6) 0.032(6) 0.026(5) 0.017(4) -0.004(4) 0.002(5) C4A 0.024(6) 0.027(6) 0.019(4) 0.005(4) 0.007(4) 0.005(5) C30A 0.022(4) 0.020(4) 0.026(5) 0.010(4) 0.003(3) 0.006(3) C30B 0.027(5) 0.018(5) 0.035(5) 0.010(4) 0.007(4) 0.005(4) C31B 0.041(5) 0.032(5) 0.031(5) 0.011(4) 0.006(4) -0.004(4) C17 0.040(3) 0.038(3) 0.037(3) 0.016(2) 0.011(2) 0.005(2) C4B 0.020(5) 0.018(5) 0.024(4) 0.006(3) -0.002(4) -0.002(4) C5A 0.022(6) 0.021(5) 0.031(5) 0.019(4) 0.010(6) 0.010(6) C21A 0.020(6) 0.012(5) 0.014(4) 0.008(3) 0.004(5) 0.000(5) O3A 0.033(6) 0.022(4) 0.035(5) 0.017(3) -0.010(4) -0.001(4) I3A 0.0432(8) 0.0472(14) 0.1041(17) 0.0529(12) -0.0018(10) 0.0079(9) O2B 0.046(10) 0.025(7) 0.018(8) 0.013(6) -0.008(6) -0.013(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 I2 C18 2.095(4) . ? I1 C11 2.105(4) . ? I3B C25B 2.127(11) . ? O2A C15 1.32(3) . ? O2A C14A 1.429(15) . ? C9 H9 0.9500 . ? C9 C8 1.369(6) . ? C9 C10 1.405(7) . ? O3B C22B 1.342(18) . ? O3B C21B 1.447(16) . ? C8 C13 1.392(6) . ? C8 O1 1.384(5) . ? C15 C20 1.391(7) . ? C15 C16 1.370(7) . ? C15 O2B 1.45(2) . ? C19 H19 0.9500 . ? C19 C18 1.386(7) . ? C19 C20 1.384(6) . ? C18 C17 1.398(6) . ? C10 H10 0.9500 . ? C10 C11 1.380(7) . ? C12 H12 0.9500 . ? C12 C13 1.359(7) . ? C12 C11 1.394(7) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C22B C27B 1.380(12) . ? C22B C23B 1.376(12) . ? C27B H27B 0.9500 . ? C27B C26B 1.397(11) . ? C23B H23B 0.9500 . ? C23B C24B 1.360(12) . ? C16 H16 0.9500 . ? C16 C17 1.389(6) . ? C25B C26B 1.389(11) . ? C25B C24B 1.368(11) . ? C26B H26B 0.9500 . ? O1 C7 1.441(5) . ? C2 C1 1.410(6) . ? C2 C28 1.527(6) . ? C2 C3B 1.512(10) . ? C2 C3A 1.329(11) . ? C1 C7 1.508(6) . ? C1 C6 1.406(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.528(7) . ? C21B H21A 0.9900 . ? C21B H21B 0.9900 . ? C21B C5B 1.50(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.534(6) . ? C32 C33 1.521(6) . ? C6 C5B 1.539(13) . ? C6 C5A 1.274(16) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.496(12) . ? C3B C4B 1.402(12) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.408(15) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C14B O2B 1.446(15) . ? C4A C30A 1.512(12) . ? C4A C3A 1.410(13) . ? C4A C5A 1.408(15) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.484(14) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.533(13) . ? C30B C4B 1.511(14) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C24B H24B 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C3A C14A 1.516(17) . ? C5A C21A 1.554(17) . ? C21A H21C 0.9900 . ? C21A H21D 0.9900 . ? C21A O3A 1.428(15) . ? O3A C22A 1.431(16) . ? C22A C27A 1.400(12) . ? C22A C23A 1.426(12) . ? C27A H27A 0.9500 . ? C27A C26A 1.397(11) . ? C26A H26A 0.9500 . ? C26A C25A 1.365(10) . ? C25A C24A 1.406(11) . ? C25A I3A 2.116(10) . ? C24A H24A 0.9500 . ? C24A C23A 1.416(11) . ? C23A H23A 0.9500 . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? 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 C15 O2A C14A 111.0(18) . . ? C8 C9 H9 120.3 . . ? C8 C9 C10 119.4(4) . . ? C10 C9 H9 120.3 . . ? C22B O3B C21B 115.6(11) . . ? C9 C8 C13 120.0(4) . . ? C9 C8 O1 124.3(4) . . ? O1 C8 C13 115.7(4) . . ? O2A C15 C20 132.0(9) . . ? O2A C15 C16 107.4(8) . . ? O2A C15 O2B 16.8(12) . . ? C20 C15 O2B 115.5(8) . . ? C16 C15 C20 120.6(4) . . ? C16 C15 O2B 123.9(8) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C20 C19 C18 119.8(4) . . ? C19 C18 I2 119.1(3) . . ? C19 C18 C17 120.6(4) . . ? C17 C18 I2 120.2(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 120.1 . . ? C13 C12 H12 120.5 . . ? C13 C12 C11 119.0(4) . . ? C11 C12 H12 120.5 . . ? C8 C13 H13 119.3 . . ? C12 C13 C8 121.4(4) . . ? C12 C13 H13 119.3 . . ? C15 C20 H20 120.2 . . ? C19 C20 C15 119.6(5) . . ? C19 C20 H20 120.2 . . ? O3B C22B C27B 122.9(11) . . ? O3B C22B C23B 112.1(11) . . ? C23B C22B C27B 125.1(12) . . ? C22B C27B H27B 121.8 . . ? C22B C27B C26B 116.4(11) . . ? C26B C27B H27B 121.8 . . ? C22B C23B H23B 121.3 . . ? C24B C23B C22B 117.4(13) . . ? C24B C23B H23B 121.3 . . ? C10 C11 I1 119.0(4) . . ? C10 C11 C12 120.5(4) . . ? C12 C11 I1 120.5(3) . . ? C15 C16 H16 119.7 . . ? C15 C16 C17 120.6(4) . . ? C17 C16 H16 119.7 . . ? C26B C25B I3B 114.5(8) . . ? C24B C25B I3B 122.9(7) . . ? C24B C25B C26B 122.6(9) . . ? C27B C26B H26B 120.7 . . ? C25B C26B C27B 118.6(10) . . ? C25B C26B H26B 120.7 . . ? C8 O1 C7 118.2(3) . . ? C1 C2 C28 121.3(4) . . ? C1 C2 C3B 118.3(4) . . ? C3B C2 C28 119.6(4) . . ? C3A C2 C1 117.8(5) . . ? C3A C2 C28 119.5(5) . . ? C3A C2 C3B 21.5(4) . . ? C2 C1 C7 118.4(4) . . ? C6 C1 C2 120.8(4) . . ? C6 C1 C7 120.5(4) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? C2 C28 C29 112.7(4) . . ? H28A C28 H28B 107.8 . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? O3B C21B H21A 109.9 . . ? O3B C21B H21B 109.9 . . ? O3B C21B C5B 108.7(12) . . ? H21A C21B H21B 108.3 . . ? C5B C21B H21A 109.9 . . ? C5B C21B H21B 109.9 . . ? O1 C7 C1 106.0(3) . . ? O1 C7 H7A 110.5 . . ? O1 C7 H7B 110.5 . . ? C1 C7 H7A 110.5 . . ? C1 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? H32A C32 H32B 107.9 . . ? C6 C32 H32A 109.1 . . ? C6 C32 H32B 109.1 . . ? C33 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? C33 C32 C6 112.3(4) . . ? C1 C6 C32 120.4(4) . . ? C1 C6 C5B 118.6(6) . . ? C32 C6 C5B 119.9(6) . . ? C5A C6 C1 119.4(6) . . ? C5A C6 C32 119.2(7) . . ? C5A C6 C5B 20.0(8) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C14B C3B C2 118.4(7) . . ? C4B C3B C2 121.3(6) . . ? C4B C3B C14B 119.1(8) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C21B C5B C6 119.5(9) . . ? C4B C5B C21B 119.6(10) . . ? C4B C5B C6 120.0(10) . . ? C3B C14B H14A 110.8 . . ? C3B C14B H14B 110.8 . . ? H14A C14B H14B 108.8 . . ? O2B C14B C3B 105.0(13) . . ? O2B C14B H14A 110.8 . . ? O2B C14B H14B 110.8 . . ? C3A C4A C30A 118.7(7) . . ? C5A C4A C30A 122.8(9) . . ? C5A C4A C3A 118.4(9) . . ? C4A C30A H30A 109.5 . . ? C4A C30A H30B 109.5 . . ? H30A C30A H30B 108.0 . . ? C31A C30A C4A 110.9(9) . . ? C31A C30A H30A 109.5 . . ? C31A C30A H30B 109.5 . . ? H30C C30B H30D 107.6 . . ? C31B C30B H30C 108.6 . . ? C31B C30B H30D 108.6 . . ? C4B C30B H30C 108.6 . . ? C4B C30B H30D 108.6 . . ? C4B C30B C31B 114.5(8) . . ? C18 C17 H17 120.6 . . ? C16 C17 C18 118.8(5) . . ? C16 C17 H17 120.6 . . ? C3B C4B C5B 119.5(9) . . ? C3B C4B C30B 120.7(7) . . ? C5B C4B C30B 119.6(8) . . ? C23B C24B C25B 119.9(11) . . ? C23B C24B H24B 120.1 . . ? C25B C24B H24B 120.1 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 120.9(7) . . ? C2 C3A C14A 119.5(9) . . ? C4A C3A C14A 119.4(9) . . ? C6 C5A C4A 121.7(11) . . ? C6 C5A C21A 121.0(10) . . ? C4A C5A C21A 117.3(11) . . ? C5A C21A H21C 109.7 . . ? C5A C21A H21D 109.7 . . ? H21C C21A H21D 108.2 . . ? O3A C21A C5A 109.7(10) . . ? O3A C21A H21C 109.7 . . ? O3A C21A H21D 109.7 . . ? C21A O3A C22A 115.7(10) . . ? C27A C22A O3A 124.7(10) . . ? C27A C22A C23A 117.4(11) . . ? C23A C22A O3A 117.9(10) . . ? C22A C27A H27A 118.7 . . ? C26A C27A C22A 122.6(11) . . ? C26A C27A H27A 118.7 . . ? C27A C26A H26A 120.4 . . ? C25A C26A C27A 119.2(10) . . ? C25A C26A H26A 120.4 . . ? C26A C25A C24A 121.3(8) . . ? C26A C25A I3A 122.0(7) . . ? C24A C25A I3A 116.6(6) . . ? C25A C24A H24A 120.3 . . ? C25A C24A C23A 119.4(9) . . ? C23A C24A H24A 120.3 . . ? C22A C23A H23A 120.1 . . ? C24A C23A C22A 119.9(11) . . ? C24A C23A H23A 120.1 . . ? O2A C14A C3A 107.8(16) . . ? O2A C14A H14C 110.2 . . ? O2A C14A H14D 110.2 . . ? C3A C14A H14C 110.2 . . ? C3A C14A H14D 110.2 . . ? H14C C14A H14D 108.5 . . ? C14B O2B C15 123.0(16) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 C18 C17 C16 178.8(4) . . . . ? I3B C25B C26B C27B 179.5(9) . . . . ? I3B C25B C24B C23B -179.1(10) . . . . ? O2A C15 C20 C19 -178.1(18) . . . . ? O2A C15 C16 C17 179.3(15) . . . . ? O2A C15 O2B C14B -178(11) . . . . ? C9 C8 C13 C12 -0.2(6) . . . . ? C9 C8 O1 C7 -1.0(6) . . . . ? C9 C10 C11 I1 176.5(3) . . . . ? C9 C10 C11 C12 -1.4(7) . . . . ? O3B C22B C27B C26B -176.6(12) . . . . ? O3B C22B C23B C24B 177.1(13) . . . . ? O3B C21B C5B C6 78.0(12) . . . . ? O3B C21B C5B C4B -113.0(13) . . . . ? C8 C9 C10 C11 -0.2(6) . . . . ? C8 O1 C7 C1 173.7(3) . . . . ? C15 O2A C14A C3A -174.8(16) . . . . ? C15 C16 C17 C18 -1.1(7) . . . . ? C19 C18 C17 C16 0.2(7) . . . . ? C18 C19 C20 C15 -0.3(7) . . . . ? C10 C9 C8 C13 1.0(6) . . . . ? C10 C9 C8 O1 -178.8(4) . . . . ? C13 C8 O1 C7 179.3(4) . . . . ? C13 C12 C11 I1 -175.6(3) . . . . ? C13 C12 C11 C10 2.2(7) . . . . ? C20 C15 C16 C17 1.3(7) . . . . ? C20 C15 O2B C14B -9(3) . . . . ? C20 C19 C18 I2 -178.1(4) . . . . ? C20 C19 C18 C17 0.4(7) . . . . ? C22B O3B C21B C5B -170.6(11) . . . . ? C22B C27B C26B C25B -0.6(17) . . . . ? C22B C23B C24B C25B 0(2) . . . . ? C27B C22B C23B C24B -2(2) . . . . ? C23B C22B C27B C26B 3(2) . . . . ? C11 C12 C13 C8 -1.4(7) . . . . ? C16 C15 C20 C19 -0.6(7) . . . . ? C16 C15 O2B C14B 169.2(15) . . . . ? C26B C25B C24B C23B 2.7(18) . . . . ? O1 C8 C13 C12 179.6(4) . . . . ? C2 C1 C7 O1 -83.7(5) . . . . ? C2 C1 C6 C32 -179.8(4) . . . . ? C2 C1 C6 C5B -11.6(9) . . . . ? C2 C1 C6 C5A 11.3(10) . . . . ? C2 C3B C14B O2B 72.1(16) . . . . ? C2 C3B C4B C5B 0.9(15) . . . . ? C2 C3B C4B C30B 176.1(9) . . . . ? C2 C3A C14A O2A 101.7(19) . . . . ? C1 C2 C28 C29 -93.6(5) . . . . ? C1 C2 C3B C14B -177.4(8) . . . . ? C1 C2 C3B C4B -10.4(11) . . . . ? C1 C2 C3A C4A 5.3(13) . . . . ? C1 C2 C3A C14A 179.4(9) . . . . ? C1 C6 C5B C21B 170.7(9) . . . . ? C1 C6 C5B C4B 1.7(14) . . . . ? C1 C6 C5A C4A -10.1(15) . . . . ? C1 C6 C5A C21A 172.8(8) . . . . ? C28 C2 C1 C7 -0.8(7) . . . . ? C28 C2 C1 C6 -174.8(4) . . . . ? C28 C2 C3B C14B 12.9(11) . . . . ? C28 C2 C3B C4B 179.9(7) . . . . ? C28 C2 C3A C4A 171.7(8) . . . . ? C28 C2 C3A C14A -14.2(13) . . . . ? C21B O3B C22B C27B -7(2) . . . . ? C21B O3B C22B C23B 173.8(12) . . . . ? C21B C5B C4B C3B -165.5(10) . . . . ? C21B C5B C4B C30B 19.1(16) . . . . ? C7 C1 C6 C32 6.3(7) . . . . ? C7 C1 C6 C5B 174.5(7) . . . . ? C7 C1 C6 C5A -162.6(8) . . . . ? C32 C6 C5B C21B -21.1(14) . . . . ? C32 C6 C5B C4B 170.0(9) . . . . ? C32 C6 C5A C4A -179.2(9) . . . . ? C32 C6 C5A C21A 3.7(14) . . . . ? C6 C1 C7 O1 90.4(5) . . . . ? C6 C5B C4B C3B 3.4(16) . . . . ? C6 C5B C4B C30B -172.0(9) . . . . ? C6 C5A C21A O3A 64.8(13) . . . . ? C33 C32 C6 C1 87.9(5) . . . . ? C33 C32 C6 C5B -80.2(8) . . . . ? C33 C32 C6 C5A -103.2(9) . . . . ? C3B C2 C1 C7 -170.3(6) . . . . ? C3B C2 C1 C6 15.7(8) . . . . ? C3B C2 C28 C29 75.8(7) . . . . ? C3B C2 C3A C4A -91.9(17) . . . . ? C3B C2 C3A C14A 82.2(18) . . . . ? C3B C14B O2B C15 -176.7(19) . . . . ? C5B C6 C5A C4A 83(3) . . . . ? C5B C6 C5A C21A -94(3) . . . . ? C14B C3B C4B C5B 167.8(11) . . . . ? C14B C3B C4B C30B -16.9(14) . . . . ? C4A C3A C14A O2A -84.1(19) . . . . ? C4A C5A C21A O3A -112.4(12) . . . . ? C30A C4A C3A C2 174.7(10) . . . . ? C30A C4A C3A C14A 0.6(16) . . . . ? C30A C4A C5A C6 -172.1(11) . . . . ? C30A C4A C5A C21A 5.0(17) . . . . ? C31B C30B C4B C3B 86.2(11) . . . . ? C31B C30B C4B C5B -98.6(11) . . . . ? C4B C3B C14B O2B -95.2(16) . . . . ? C24B C25B C26B C27B -2.1(16) . . . . ? C3A C2 C1 C7 165.3(7) . . . . ? C3A C2 C1 C6 -8.8(9) . . . . ? C3A C2 C28 C29 100.6(7) . . . . ? C3A C2 C3B C14B -83.0(17) . . . . ? C3A C2 C3B C4B 84.0(17) . . . . ? C3A C4A C30A C31A -100.1(11) . . . . ? C3A C4A C5A C6 6.7(18) . . . . ? C3A C4A C5A C21A -176.1(10) . . . . ? C5A C6 C5B C21B 73(3) . . . . ? C5A C6 C5B C4B -96(3) . . . . ? C5A C4A C30A C31A 78.7(14) . . . . ? C5A C4A C3A C2 -4.2(16) . . . . ? C5A C4A C3A C14A -178.3(12) . . . . ? C5A C21A O3A C22A 178.5(10) . . . . ? C21A O3A C22A C27A -15.5(19) . . . . ? C21A O3A C22A C23A 164.9(11) . . . . ? O3A C22A C27A C26A 176.5(12) . . . . ? O3A C22A C23A C24A -175.5(11) . . . . ? C22A C27A C26A C25A 1.7(19) . . . . ? C27A C22A C23A C24A 4.9(19) . . . . ? C27A C26A C25A C24A -0.4(15) . . . . ? C27A C26A C25A I3A -176.9(9) . . . . ? C26A C25A C24A C23A 1.5(15) . . . . ? C25A C24A C23A C22A -3.8(17) . . . . ? C23A C22A C27A C26A -4(2) . . . . ? I3A C25A C24A C23A 178.2(8) . . . . ? C14A O2A C15 C20 -16(3) . . . . ? C14A O2A C15 C16 166.2(17) . . . . ? C14A O2A C15 O2B -3(6) . . . . ? O2B C15 C20 C19 177.8(13) . . . . ? O2B C15 C16 C17 -176.9(14) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.030 0.500 0.000 379 50 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962435' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-ea-154K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-ea, 154 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 I3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 I3 O5' _chemical_formula_weight 946.40 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.8405(7) _cell_length_b 13.2389(11) _cell_length_c 15.5067(10) _cell_angle_alpha 111.319(7) _cell_angle_beta 94.776(5) _cell_angle_gamma 91.678(6) _cell_volume 1871.5(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5387 _cell_measurement_temperature 154(2) _cell_measurement_theta_max 29.1672 _cell_measurement_theta_min 3.7537 _exptl_absorpt_coefficient_mu 2.544 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.45861 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 924 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0629 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 8576 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.23 _diffrn_reflns_theta_min 3.76 _diffrn_ambient_temperature 154(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.843 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0642979000 _diffrn_orient_matrix_UB_12 0.0050189000 _diffrn_orient_matrix_UB_13 0.0182149000 _diffrn_orient_matrix_UB_21 0.0322000000 _diffrn_orient_matrix_UB_22 0.0318123000 _diffrn_orient_matrix_UB_23 0.0447959000 _diffrn_orient_matrix_UB_31 -0.0090750000 _diffrn_orient_matrix_UB_32 0.0477927000 _diffrn_orient_matrix_UB_33 -0.0098632000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5936 _reflns_number_total 8576 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.456 _refine_diff_density_min -1.194 _refine_diff_density_rms 0.129 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 416 _refine_ls_number_reflns 8576 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0493 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1219 _refine_ls_wR_factor_ref 0.1368 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 3. Others Sof(O2A)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(O3A)=Sof(C22A)= Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(C24A)=Sof(H24A)= Sof(C23A)=Sof(H23A)=Sof(I3A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1) Sof(I3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C24B)=Sof(H24B)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I2 I 1.00055(4) 0.14020(3) 0.97657(2) 0.04968(13) Uani 1 1 d . . . I1 I 1.70937(4) 0.03683(3) 0.12839(2) 0.04923(13) Uani 1 1 d . . . I3B I 0.5108(8) 0.9575(6) 0.3315(6) 0.0850(15) Uani 0.515(11) 1 d A 1 . O2A O 0.9658(11) 0.2809(8) 0.6359(7) 0.040(3) Uiso 0.485(11) 1 d A 2 . C9 C 1.2919(5) 0.1128(4) 0.1863(3) 0.0344(10) Uani 1 1 d . . . H9 H 1.2033 0.0845 0.1563 0.041 Uiso 1 1 calc . . R O3B O 0.6820(12) 0.5306(11) 0.3670(9) 0.031(3) Uiso 0.515(11) 1 d A 1 . C8 C 1.3067(5) 0.1975(3) 0.2709(3) 0.0306(10) Uani 1 1 d . . . C15 C 0.9526(5) 0.2517(4) 0.7107(3) 0.0385(11) Uani 1 1 d . . . C19 C 0.8586(5) 0.1644(4) 0.8056(4) 0.0408(12) Uani 1 1 d . . . H19 H 0.7852 0.1259 0.8188 0.049 Uiso 1 1 calc A . R C18 C 0.9793(5) 0.1896(4) 0.8626(3) 0.0366(11) Uani 1 1 d A . . C10 C 1.4078(5) 0.0685(4) 0.1445(3) 0.0373(11) Uani 1 1 d . . . H10 H 1.3985 0.0096 0.0863 0.045 Uiso 1 1 calc . . R C12 C 1.5508(5) 0.1971(4) 0.2733(4) 0.0409(11) Uani 1 1 d . . . H12 H 1.6393 0.2262 0.3029 0.049 Uiso 1 1 calc . . R C13 C 1.4370(5) 0.2402(4) 0.3143(3) 0.0373(11) Uani 1 1 d . . . H13 H 1.4466 0.2993 0.3724 0.045 Uiso 1 1 calc . . R C20 C 0.8437(5) 0.1948(4) 0.7290(4) 0.0429(12) Uani 1 1 d A . . H20 H 0.7605 0.1773 0.6894 0.052 Uiso 1 1 calc . . R C22B C 0.6623(15) 0.6224(11) 0.3582(9) 0.033(4) Uiso 0.515(11) 1 d A 1 . C27B C 0.7038(12) 0.7216(8) 0.4262(9) 0.032(3) Uiso 0.515(11) 1 d A 1 . H27B H 0.7631 0.7261 0.4792 0.039 Uiso 0.515(11) 1 calc A 1 R C23B C 0.5791(14) 0.6156(12) 0.2812(9) 0.039(4) Uiso 0.515(11) 1 d A 1 . H23B H 0.5519 0.5464 0.2349 0.047 Uiso 0.515(11) 1 calc A 1 R C11 C 1.5363(5) 0.1107(4) 0.1884(3) 0.0358(10) Uani 1 1 d . . . C16 C 1.0720(5) 0.2775(4) 0.7688(4) 0.0420(12) Uani 1 1 d A . . H16 H 1.1449 0.3168 0.7559 0.050 Uiso 1 1 calc . . R C25B C 0.5711(10) 0.8062(9) 0.3374(8) 0.031(2) Uiso 0.515(11) 1 d A 1 . C26B C 0.6571(10) 0.8156(8) 0.4159(8) 0.034(3) Uiso 0.515(11) 1 d A 1 . H26B H 0.6840 0.8851 0.4620 0.041 Uiso 0.515(11) 1 calc A 1 R O1 O 1.1989(3) 0.2455(2) 0.3196(2) 0.0370(7) Uani 1 1 d A . . C2 C 0.9441(5) 0.2243(4) 0.4203(3) 0.0357(11) Uani 1 1 d . . . C1 C 0.9698(5) 0.2655(4) 0.3515(3) 0.0333(10) Uani 1 1 d A . . C28 C 1.0065(5) 0.1217(4) 0.4218(3) 0.0357(11) Uani 1 1 d A . . H28A H 1.0288 0.1289 0.4873 0.043 Uiso 1 1 calc . . R H28B H 1.0931 0.1140 0.3925 0.043 Uiso 1 1 calc . . R C21B C 0.7780(15) 0.5280(16) 0.4378(13) 0.031(3) Uani 0.515(11) 1 d A 1 . H21A H 0.7392 0.5587 0.4982 0.037 Uiso 0.515(11) 1 calc A 1 R H21B H 0.8603 0.5743 0.4405 0.037 Uiso 0.515(11) 1 calc A 1 R C7 C 1.0606(4) 0.2049(4) 0.2779(3) 0.0326(10) Uani 1 1 d . . . H7A H 1.0483 0.1255 0.2626 0.039 Uiso 1 1 calc A . R H7B H 1.0398 0.2201 0.2204 0.039 Uiso 1 1 calc . . R C32 C 0.9462(5) 0.4084(4) 0.2780(3) 0.0402(11) Uani 1 1 d A . . H32A H 1.0363 0.3867 0.2559 0.048 Uiso 1 1 calc . . R H32B H 0.9494 0.4887 0.3050 0.048 Uiso 1 1 calc . . R C6 C 0.9196(5) 0.3638(4) 0.3531(3) 0.0343(10) Uani 1 1 d . . . C33 C 0.8359(5) 0.3670(5) 0.1953(3) 0.0443(12) Uani 1 1 d . . . H33A H 0.8594 0.3943 0.1472 0.066 Uiso 1 1 calc A . GR H33B H 0.7476 0.3928 0.2161 0.066 Uiso 1 1 calc . . GR H33C H 0.8303 0.2874 0.1697 0.066 Uiso 1 1 calc . . GR C3B C 0.8378(13) 0.2729(9) 0.4836(8) 0.029(2) Uani 0.515(11) 1 d A 1 . C29 C 0.9138(5) 0.0191(4) 0.3717(4) 0.0430(12) Uani 1 1 d . . . H29A H 0.8913 0.0112 0.3067 0.065 Uiso 1 1 calc A . GR H29B H 0.8296 0.0244 0.4023 0.065 Uiso 1 1 calc . . GR H29C H 0.9609 -0.0443 0.3739 0.065 Uiso 1 1 calc . . GR C5B C 0.8185(13) 0.4166(13) 0.4240(11) 0.020(2) Uani 0.515(11) 1 d A 1 . C14B C 0.8139(15) 0.2334(10) 0.5603(8) 0.028(2) Uani 0.515(11) 1 d A 1 . H14A H 0.8128 0.1531 0.5376 0.034 Uiso 0.515(11) 1 calc A 1 R H14B H 0.7253 0.2562 0.5846 0.034 Uiso 0.515(11) 1 calc A 1 R C4A C 0.8445(14) 0.3900(10) 0.5002(8) 0.032(3) Uani 0.485(11) 1 d A 2 . C30A C 0.7708(10) 0.4565(8) 0.5819(7) 0.035(3) Uani 0.485(11) 1 d A 2 . H30A H 0.7923 0.4326 0.6348 0.042 Uiso 0.485(11) 1 calc A 2 R H30B H 0.8019 0.5341 0.6020 0.042 Uiso 0.485(11) 1 calc A 2 R C30B C 0.6634(12) 0.4107(10) 0.5436(9) 0.028(3) Uani 0.515(11) 1 d A 1 . H30C H 0.6061 0.3486 0.5448 0.034 Uiso 0.515(11) 1 calc A 1 R H30D H 0.6051 0.4510 0.5138 0.034 Uiso 0.515(11) 1 calc A 1 R C31B C 0.7066(10) 0.4847(7) 0.6428(7) 0.038(3) Uani 0.515(11) 1 d A 1 . H31A H 0.7612 0.5480 0.6432 0.058 Uiso 0.515(11) 1 calc A 1 GR H31B H 0.7613 0.4453 0.6744 0.058 Uiso 0.515(11) 1 calc A 1 GR H31C H 0.6253 0.5089 0.6753 0.058 Uiso 0.515(11) 1 calc A 1 GR C17 C 1.0883(5) 0.2479(4) 0.8447(4) 0.0423(12) Uani 1 1 d . . . H17 H 1.1714 0.2663 0.8845 0.051 Uiso 1 1 calc A . R C4B C 0.7758(11) 0.3663(8) 0.4833(7) 0.023(2) Uani 0.515(11) 1 d A 1 . C24B C 0.5344(11) 0.7074(9) 0.2698(8) 0.036(3) Uiso 0.515(11) 1 d A 1 . H24B H 0.4783 0.7021 0.2152 0.043 Uiso 0.515(11) 1 calc A 1 R C31A C 0.6213(15) 0.4430(13) 0.5551(12) 0.043(4) Uani 0.485(11) 1 d A 2 . H31D H 0.5991 0.4758 0.5087 0.065 Uiso 0.485(11) 1 calc A 2 GR H31E H 0.5736 0.4788 0.6102 0.065 Uiso 0.485(11) 1 calc A 2 GR H31F H 0.5925 0.3654 0.5287 0.065 Uiso 0.485(11) 1 calc A 2 GR C3A C 0.8833(13) 0.2857(11) 0.4940(10) 0.027(3) Uiso 0.485(11) 1 d A 2 . C5A C 0.8702(14) 0.4278(15) 0.4269(13) 0.026(3) Uani 0.485(11) 1 d A 2 . C21A C 0.8259(16) 0.5406(14) 0.4355(12) 0.022(3) Uani 0.485(11) 1 d A 2 . H21C H 0.7940 0.5775 0.4976 0.027 Uiso 0.485(11) 1 calc A 2 R H21D H 0.9050 0.5849 0.4297 0.027 Uiso 0.485(11) 1 calc A 2 R O3A O 0.7190(14) 0.5324(11) 0.3651(10) 0.039(3) Uani 0.485(11) 1 d A 2 . C22A C 0.6596(15) 0.6384(11) 0.3729(9) 0.031(4) Uiso 0.485(11) 1 d A 2 . C27A C 0.6905(12) 0.7342(8) 0.4485(9) 0.028(3) Uiso 0.485(11) 1 d A 2 . H27A H 0.7415 0.7331 0.5029 0.034 Uiso 0.485(11) 1 calc A 2 R C26A C 0.6477(10) 0.8325(8) 0.4457(8) 0.026(2) Uiso 0.485(11) 1 d A 2 . H26A H 0.6717 0.8984 0.4971 0.031 Uiso 0.485(11) 1 calc A 2 R C25A C 0.5708(9) 0.8332(8) 0.3684(7) 0.025(2) Uiso 0.485(11) 1 d A 2 . C24A C 0.5337(11) 0.7392(9) 0.2934(8) 0.030(3) Uiso 0.485(11) 1 d A 2 . H24A H 0.4795 0.7410 0.2404 0.037 Uiso 0.485(11) 1 calc A 2 R C23A C 0.5767(15) 0.6414(12) 0.2963(10) 0.041(4) Uiso 0.485(11) 1 d A 2 . H23A H 0.5495 0.5756 0.2455 0.049 Uiso 0.485(11) 1 calc A 2 R I3A I 0.5050(9) 0.9753(5) 0.3549(5) 0.0640(8) Uani 0.485(11) 1 d A 2 . C14A C 0.8585(15) 0.2446(14) 0.5695(12) 0.037(4) Uiso 0.485(11) 1 d A 2 . H14C H 0.7728 0.2716 0.5963 0.044 Uiso 0.485(11) 1 calc A 2 R H14D H 0.8500 0.1642 0.5443 0.044 Uiso 0.485(11) 1 calc A 2 R O2B O 0.9292(10) 0.2831(7) 0.6347(6) 0.034(2) Uiso 0.515(11) 1 d A 1 . 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 I2 0.0551(2) 0.0653(3) 0.0402(2) 0.03112(18) 0.01070(16) 0.01127(18) I1 0.0360(2) 0.0651(3) 0.0452(2) 0.01869(18) 0.00303(15) 0.00514(16) I3B 0.0369(8) 0.087(3) 0.178(5) 0.106(3) -0.003(3) 0.0067(19) C9 0.029(3) 0.036(3) 0.038(3) 0.016(2) -0.0075(19) -0.001(2) C8 0.031(2) 0.027(2) 0.034(2) 0.0135(19) -0.0068(19) -0.0025(18) C15 0.050(3) 0.034(3) 0.040(3) 0.021(2) 0.019(2) 0.012(2) C19 0.038(3) 0.052(3) 0.047(3) 0.033(3) 0.014(2) 0.006(2) C18 0.039(3) 0.044(3) 0.037(3) 0.024(2) 0.014(2) 0.010(2) C10 0.039(3) 0.039(3) 0.033(3) 0.013(2) -0.003(2) 0.004(2) C12 0.035(3) 0.045(3) 0.046(3) 0.022(2) -0.001(2) -0.005(2) C13 0.037(3) 0.034(3) 0.037(3) 0.012(2) -0.008(2) -0.009(2) C20 0.036(3) 0.057(3) 0.049(3) 0.035(3) 0.008(2) 0.004(2) C11 0.033(3) 0.039(3) 0.041(3) 0.021(2) 0.001(2) 0.000(2) C16 0.044(3) 0.038(3) 0.049(3) 0.020(2) 0.014(2) -0.005(2) O1 0.0300(18) 0.0364(18) 0.0385(19) 0.0089(14) -0.0039(14) -0.0078(14) C2 0.043(3) 0.030(2) 0.038(3) 0.019(2) -0.001(2) 0.001(2) C1 0.038(3) 0.031(2) 0.031(3) 0.013(2) -0.001(2) 0.001(2) C28 0.038(3) 0.032(2) 0.041(3) 0.018(2) -0.002(2) 0.004(2) C21B 0.026(8) 0.040(8) 0.041(6) 0.028(5) 0.013(7) -0.002(6) C7 0.030(2) 0.032(2) 0.033(3) 0.0107(19) -0.0044(19) -0.0030(19) C32 0.040(3) 0.044(3) 0.044(3) 0.026(2) 0.001(2) -0.002(2) C6 0.039(3) 0.032(2) 0.034(3) 0.016(2) -0.004(2) 0.002(2) C33 0.043(3) 0.066(3) 0.028(3) 0.022(2) 0.002(2) 0.010(3) C3B 0.023(6) 0.032(6) 0.041(6) 0.024(5) 0.001(5) -0.002(5) C29 0.044(3) 0.032(3) 0.052(3) 0.015(2) -0.002(2) 0.004(2) C5B 0.017(7) 0.017(5) 0.031(5) 0.013(4) 0.011(6) -0.001(6) C14B 0.024(6) 0.029(6) 0.031(6) 0.013(4) -0.005(5) 0.002(5) C4A 0.031(7) 0.037(6) 0.031(6) 0.013(5) 0.007(5) 0.003(5) C30A 0.029(6) 0.044(6) 0.039(6) 0.023(5) 0.005(4) 0.009(4) C30B 0.019(7) 0.028(6) 0.046(6) 0.021(5) 0.008(5) 0.015(4) C31B 0.041(6) 0.030(5) 0.046(6) 0.014(4) 0.014(5) 0.000(4) C17 0.034(3) 0.051(3) 0.045(3) 0.021(2) 0.004(2) -0.003(2) C4B 0.019(5) 0.020(5) 0.031(5) 0.010(4) 0.000(4) 0.000(4) C31A 0.019(8) 0.049(10) 0.070(9) 0.030(8) 0.013(6) 0.015(5) C5A 0.015(7) 0.029(6) 0.042(6) 0.021(5) 0.009(7) -0.003(6) C21A 0.028(8) 0.016(5) 0.029(6) 0.013(4) 0.006(6) -0.003(6) O3A 0.034(7) 0.038(5) 0.058(6) 0.031(4) 0.010(6) 0.010(5) I3A 0.0437(15) 0.0549(10) 0.1117(17) 0.0559(11) -0.0085(10) 0.0045(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 I2 C18 2.094(4) . ? I1 C11 2.103(5) . ? I3B C25B 2.137(12) . ? O2A C15 1.365(10) . ? O2A C14A 1.354(18) . ? C9 H9 0.9500 . ? C9 C8 1.375(6) . ? C9 C10 1.396(7) . ? O3B C22B 1.29(2) . ? O3B C21B 1.40(2) . ? C8 C13 1.397(6) . ? C8 O1 1.387(5) . ? C15 C20 1.398(7) . ? C15 C16 1.372(7) . ? C15 O2B 1.390(10) . ? C19 H19 0.9500 . ? C19 C18 1.375(7) . ? C19 C20 1.385(6) . ? C18 C17 1.407(6) . ? C10 H10 0.9500 . ? C10 C11 1.382(7) . ? C12 H12 0.9500 . ? C12 C13 1.370(7) . ? C12 C11 1.388(7) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C22B C27B 1.376(12) . ? C22B C23B 1.362(11) . ? C27B H27B 0.9500 . ? C27B C26B 1.396(10) . ? C23B H23B 0.9500 . ? C23B C24B 1.370(11) . ? C16 H16 0.9500 . ? C16 C17 1.370(7) . ? C25B C26B 1.387(11) . ? C25B C24B 1.361(11) . ? C26B H26B 0.9500 . ? O1 C7 1.456(5) . ? C2 C1 1.401(6) . ? C2 C28 1.514(6) . ? C2 C3B 1.491(13) . ? C2 C3A 1.339(15) . ? C1 C7 1.513(6) . ? C1 C6 1.399(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.524(7) . ? C21B H21A 0.9900 . ? C21B H21B 0.9900 . ? C21B C5B 1.48(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.521(6) . ? C32 C33 1.531(7) . ? C6 C5B 1.533(15) . ? C6 C5A 1.294(19) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.496(15) . ? C3B C4B 1.396(14) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.401(17) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C14B O2B 1.496(15) . ? C4A C30A 1.512(15) . ? C4A C3A 1.415(18) . ? C4A C5A 1.44(2) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.482(17) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.509(17) . ? C30B C4B 1.502(16) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C24B H24B 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C3A C14A 1.49(2) . ? C5A C21A 1.53(3) . ? C21A H21C 0.9900 . ? C21A H21D 0.9900 . ? C21A O3A 1.42(2) . ? O3A C22A 1.50(2) . ? C22A C27A 1.383(12) . ? C22A C23A 1.398(12) . ? C27A H27A 0.9500 . ? C27A C26A 1.393(10) . ? C26A H26A 0.9500 . ? C26A C25A 1.367(11) . ? C25A C24A 1.372(11) . ? C25A I3A 2.082(12) . ? C24A H24A 0.9500 . ? C24A C23A 1.389(12) . ? C23A H23A 0.9500 . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? 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 C14A O2A C15 113.5(10) . . ? C8 C9 H9 120.2 . . ? C8 C9 C10 119.6(4) . . ? C10 C9 H9 120.2 . . ? C22B O3B C21B 118.8(13) . . ? C9 C8 C13 120.2(4) . . ? C9 C8 O1 124.4(4) . . ? O1 C8 C13 115.4(4) . . ? O2A C15 C20 129.3(6) . . ? O2A C15 C16 110.4(6) . . ? O2A C15 O2B 15.1(6) . . ? C16 C15 C20 120.1(4) . . ? C16 C15 O2B 123.7(6) . . ? O2B C15 C20 116.2(6) . . ? C18 C19 H19 119.9 . . ? C18 C19 C20 120.2(4) . . ? C20 C19 H19 119.9 . . ? C19 C18 I2 119.5(3) . . ? C19 C18 C17 120.6(4) . . ? C17 C18 I2 119.9(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.7(4) . . ? C11 C10 H10 120.1 . . ? C13 C12 H12 120.1 . . ? C13 C12 C11 119.7(5) . . ? C11 C12 H12 120.1 . . ? C8 C13 H13 119.9 . . ? C12 C13 C8 120.2(5) . . ? C12 C13 H13 119.9 . . ? C15 C20 H20 120.4 . . ? C19 C20 C15 119.1(5) . . ? C19 C20 H20 120.4 . . ? O3B C22B C27B 123.8(12) . . ? O3B C22B C23B 114.8(12) . . ? C23B C22B C27B 120.8(12) . . ? C22B C27B H27B 120.6 . . ? C22B C27B C26B 118.8(11) . . ? C26B C27B H27B 120.6 . . ? C22B C23B H23B 119.6 . . ? C22B C23B C24B 120.8(13) . . ? C24B C23B H23B 119.6 . . ? C10 C11 I1 119.1(4) . . ? C10 C11 C12 120.5(5) . . ? C12 C11 I1 120.3(4) . . ? C15 C16 H16 119.3 . . ? C17 C16 C15 121.5(4) . . ? C17 C16 H16 119.3 . . ? C26B C25B I3B 114.5(7) . . ? C24B C25B I3B 124.5(7) . . ? C24B C25B C26B 121.0(9) . . ? C27B C26B H26B 120.4 . . ? C25B C26B C27B 119.1(10) . . ? C25B C26B H26B 120.4 . . ? C8 O1 C7 118.0(3) . . ? C1 C2 C28 120.9(4) . . ? C1 C2 C3B 118.9(5) . . ? C3B C2 C28 119.6(5) . . ? C3A C2 C1 119.1(7) . . ? C3A C2 C28 119.0(7) . . ? C3A C2 C3B 18.0(7) . . ? C2 C1 C7 118.7(4) . . ? C6 C1 C2 121.1(4) . . ? C6 C1 C7 120.1(4) . . ? C2 C28 H28A 108.9 . . ? C2 C28 H28B 108.9 . . ? C2 C28 C29 113.6(4) . . ? H28A C28 H28B 107.7 . . ? C29 C28 H28A 108.9 . . ? C29 C28 H28B 108.9 . . ? O3B C21B H21A 109.1 . . ? O3B C21B H21B 109.1 . . ? O3B C21B C5B 112.7(15) . . ? H21A C21B H21B 107.8 . . ? C5B C21B H21A 109.1 . . ? C5B C21B H21B 109.1 . . ? O1 C7 C1 104.7(4) . . ? O1 C7 H7A 110.8 . . ? O1 C7 H7B 110.8 . . ? C1 C7 H7A 110.8 . . ? C1 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? H32A C32 H32B 107.9 . . ? C6 C32 H32A 109.2 . . ? C6 C32 H32B 109.2 . . ? C6 C32 C33 112.1(4) . . ? C33 C32 H32A 109.2 . . ? C33 C32 H32B 109.2 . . ? C1 C6 C32 121.3(4) . . ? C1 C6 C5B 117.8(7) . . ? C32 C6 C5B 120.3(7) . . ? C5A C6 C1 119.9(9) . . ? C5A C6 C32 117.8(9) . . ? C5A C6 C5B 18.8(8) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 119.5(9) . . ? C4B C3B C2 121.5(8) . . ? C4B C3B C14B 118.2(10) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C21B C5B C6 119.7(10) . . ? C4B C5B C21B 119.1(12) . . ? C4B C5B C6 120.8(12) . . ? C3B C14B H14A 110.5 . . ? C3B C14B H14B 110.5 . . ? C3B C14B O2B 106.3(10) . . ? H14A C14B H14B 108.7 . . ? O2B C14B H14A 110.5 . . ? O2B C14B H14B 110.5 . . ? C3A C4A C30A 118.9(10) . . ? C3A C4A C5A 119.3(12) . . ? C5A C4A C30A 121.7(12) . . ? C4A C30A H30A 109.7 . . ? C4A C30A H30B 109.7 . . ? H30A C30A H30B 108.2 . . ? C31A C30A C4A 109.9(11) . . ? C31A C30A H30A 109.7 . . ? C31A C30A H30B 109.7 . . ? H30C C30B H30D 107.3 . . ? C31B C30B H30C 108.1 . . ? C31B C30B H30D 108.1 . . ? C4B C30B H30C 108.1 . . ? C4B C30B H30D 108.1 . . ? C4B C30B C31B 116.6(11) . . ? C18 C17 H17 120.8 . . ? C16 C17 C18 118.5(5) . . ? C16 C17 H17 120.8 . . ? C3B C4B C5B 118.7(10) . . ? C3B C4B C30B 120.8(9) . . ? C5B C4B C30B 120.5(10) . . ? C23B C24B H24B 120.3 . . ? C25B C24B C23B 119.3(10) . . ? C25B C24B H24B 120.3 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 119.5(11) . . ? C2 C3A C14A 120.0(12) . . ? C4A C3A C14A 120.5(12) . . ? C6 C5A C4A 119.9(15) . . ? C6 C5A C21A 121.9(14) . . ? C4A C5A C21A 117.9(14) . . ? C5A C21A H21C 109.6 . . ? C5A C21A H21D 109.6 . . ? H21C C21A H21D 108.1 . . ? O3A C21A C5A 110.5(13) . . ? O3A C21A H21C 109.6 . . ? O3A C21A H21D 109.6 . . ? C21A O3A C22A 114.5(12) . . ? C27A C22A O3A 123.8(11) . . ? C27A C22A C23A 118.4(12) . . ? C23A C22A O3A 117.7(11) . . ? C22A C27A H27A 119.6 . . ? C22A C27A C26A 120.7(11) . . ? C26A C27A H27A 119.6 . . ? C27A C26A H26A 120.3 . . ? C25A C26A C27A 119.3(10) . . ? C25A C26A H26A 120.3 . . ? C26A C25A C24A 121.6(9) . . ? C26A C25A I3A 122.8(7) . . ? C24A C25A I3A 115.6(7) . . ? C25A C24A H24A 120.5 . . ? C25A C24A C23A 118.9(10) . . ? C23A C24A H24A 120.5 . . ? C22A C23A H23A 119.6 . . ? C24A C23A C22A 120.9(12) . . ? C24A C23A H23A 119.6 . . ? O2A C14A C3A 107.9(11) . . ? O2A C14A H14C 110.1 . . ? O2A C14A H14D 110.1 . . ? C3A C14A H14C 110.1 . . ? C3A C14A H14D 110.1 . . ? H14C C14A H14D 108.4 . . ? C15 O2B C14B 122.4(7) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 C18 C17 C16 179.0(4) . . . . ? I3B C25B C26B C27B -179.4(8) . . . . ? I3B C25B C24B C23B -179.9(9) . . . . ? O2A C15 C20 C19 173.3(7) . . . . ? O2A C15 C16 C17 -174.3(6) . . . . ? O2A C15 O2B C14B 135(3) . . . . ? C9 C8 C13 C12 -0.8(7) . . . . ? C9 C8 O1 C7 -1.0(6) . . . . ? C9 C10 C11 I1 176.3(3) . . . . ? C9 C10 C11 C12 -0.3(7) . . . . ? O3B C22B C27B C26B -169.2(13) . . . . ? O3B C22B C23B C24B 170.9(13) . . . . ? O3B C21B C5B C6 77.5(13) . . . . ? O3B C21B C5B C4B -109.6(14) . . . . ? C8 C9 C10 C11 -0.4(7) . . . . ? C8 O1 C7 C1 174.6(3) . . . . ? C15 O2A C14A C3A 177.7(10) . . . . ? C15 C16 C17 C18 0.1(8) . . . . ? C19 C18 C17 C16 -0.8(8) . . . . ? C18 C19 C20 C15 -0.2(8) . . . . ? C10 C9 C8 C13 1.0(6) . . . . ? C10 C9 C8 O1 -178.2(4) . . . . ? C13 C8 O1 C7 179.8(4) . . . . ? C13 C12 C11 I1 -176.1(3) . . . . ? C13 C12 C11 C10 0.5(7) . . . . ? C20 C15 C16 C17 0.6(8) . . . . ? C20 C15 O2B C14B -17.5(11) . . . . ? C20 C19 C18 I2 -178.9(4) . . . . ? C20 C19 C18 C17 0.9(8) . . . . ? C22B O3B C21B C5B -163.8(13) . . . . ? C22B C27B C26B C25B -0.3(17) . . . . ? C22B C23B C24B C25B -2(2) . . . . ? C27B C22B C23B C24B 0(2) . . . . ? C23B C22B C27B C26B 1(2) . . . . ? C11 C12 C13 C8 0.0(7) . . . . ? C16 C15 C20 C19 -0.5(8) . . . . ? C16 C15 O2B C14B 165.3(8) . . . . ? C26B C25B C24B C23B 2.5(16) . . . . ? O1 C8 C13 C12 178.5(4) . . . . ? C2 C1 C7 O1 -85.5(5) . . . . ? C2 C1 C6 C32 -179.4(5) . . . . ? C2 C1 C6 C5B -8.7(9) . . . . ? C2 C1 C6 C5A 12.7(10) . . . . ? C2 C3B C14B O2B 76.5(12) . . . . ? C2 C3B C4B C5B -2.1(17) . . . . ? C2 C3B C4B C30B 176.5(11) . . . . ? C2 C3A C14A O2A 93.3(15) . . . . ? C1 C2 C28 C29 -94.0(6) . . . . ? C1 C2 C3B C14B -177.1(8) . . . . ? C1 C2 C3B C4B -7.9(14) . . . . ? C1 C2 C3A C4A 1.0(14) . . . . ? C1 C2 C3A C14A -178.2(9) . . . . ? C1 C6 C5B C21B 171.2(11) . . . . ? C1 C6 C5B C4B -1.5(14) . . . . ? C1 C6 C5A C4A -11.0(15) . . . . ? C1 C6 C5A C21A 174.3(10) . . . . ? C28 C2 C1 C7 0.5(7) . . . . ? C28 C2 C1 C6 -175.9(4) . . . . ? C28 C2 C3B C14B 12.0(13) . . . . ? C28 C2 C3B C4B -178.8(8) . . . . ? C28 C2 C3A C4A 169.7(9) . . . . ? C28 C2 C3A C14A -9.5(14) . . . . ? C21B O3B C22B C27B -16(2) . . . . ? C21B O3B C22B C23B 172.7(13) . . . . ? C21B C5B C4B C3B -166.1(12) . . . . ? C21B C5B C4B C30B 15.3(18) . . . . ? C7 C1 C6 C32 4.2(7) . . . . ? C7 C1 C6 C5B 174.9(7) . . . . ? C7 C1 C6 C5A -163.7(8) . . . . ? C32 C6 C5B C21B -18.0(15) . . . . ? C32 C6 C5B C4B 169.3(9) . . . . ? C32 C6 C5A C4A -179.4(9) . . . . ? C32 C6 C5A C21A 6.0(15) . . . . ? C6 C1 C7 O1 91.0(5) . . . . ? C6 C5B C4B C3B 6.7(17) . . . . ? C6 C5B C4B C30B -171.9(10) . . . . ? C6 C5A C21A O3A 61.0(15) . . . . ? C33 C32 C6 C1 88.9(6) . . . . ? C33 C32 C6 C5B -81.6(8) . . . . ? C33 C32 C6 C5A -102.9(9) . . . . ? C3B C2 C1 C7 -170.3(7) . . . . ? C3B C2 C1 C6 13.3(9) . . . . ? C3B C2 C28 C29 76.8(8) . . . . ? C3B C2 C3A C4A -93(3) . . . . ? C3B C2 C3A C14A 88(3) . . . . ? C3B C14B O2B C15 -169.9(8) . . . . ? C5B C6 C5A C4A 78(4) . . . . ? C5B C6 C5A C21A -97(5) . . . . ? C14B C3B C4B C5B 167.2(11) . . . . ? C14B C3B C4B C30B -14.2(17) . . . . ? C4A C3A C14A O2A -85.9(15) . . . . ? C4A C5A C21A O3A -113.7(14) . . . . ? C30A C4A C3A C2 177.5(11) . . . . ? C30A C4A C3A C14A -3.3(18) . . . . ? C30A C4A C5A C6 -172.2(12) . . . . ? C30A C4A C5A C21A 2.6(18) . . . . ? C31B C30B C4B C3B 84.7(13) . . . . ? C31B C30B C4B C5B -96.7(13) . . . . ? C4B C3B C14B O2B -93.1(12) . . . . ? C24B C25B C26B C27B -1.5(16) . . . . ? C3A C2 C1 C7 169.1(7) . . . . ? C3A C2 C1 C6 -7.4(9) . . . . ? C3A C2 C28 C29 97.4(8) . . . . ? C3A C2 C3B C14B -81(3) . . . . ? C3A C2 C3B C4B 88(3) . . . . ? C3A C4A C30A C31A -96.7(13) . . . . ? C3A C4A C5A C6 4.7(18) . . . . ? C3A C4A C5A C21A 179.6(12) . . . . ? C5A C6 C5B C21B 70(4) . . . . ? C5A C6 C5B C4B -103(5) . . . . ? C5A C4A C30A C31A 80.3(15) . . . . ? C5A C4A C3A C2 0.5(17) . . . . ? C5A C4A C3A C14A 179.7(12) . . . . ? C5A C21A O3A C22A 174.7(12) . . . . ? C21A O3A C22A C27A -9(2) . . . . ? C21A O3A C22A C23A 166.2(14) . . . . ? O3A C22A C27A C26A 170.7(12) . . . . ? O3A C22A C23A C24A -171.1(12) . . . . ? C22A C27A C26A C25A 2.0(17) . . . . ? C27A C22A C23A C24A 4(2) . . . . ? C27A C26A C25A C24A 0.5(16) . . . . ? C27A C26A C25A I3A -178.4(8) . . . . ? C26A C25A C24A C23A -0.6(16) . . . . ? C25A C24A C23A C22A -2(2) . . . . ? C23A C22A C27A C26A -4(2) . . . . ? I3A C25A C24A C23A 178.4(10) . . . . ? C14A O2A C15 C20 -2.8(14) . . . . ? C14A O2A C15 C16 171.5(10) . . . . ? C14A O2A C15 O2B -35(2) . . . . ? O2B C15 C20 C19 -177.8(6) . . . . ? O2B C15 C16 C17 177.7(6) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.029 0.500 0.000 390 44 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962436' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-ea-190K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-ea, 190 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 I3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 I3 O5' _chemical_formula_weight 946.40 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.8581(4) _cell_length_b 13.2593(6) _cell_length_c 15.5438(6) _cell_angle_alpha 111.200(4) _cell_angle_beta 94.483(3) _cell_angle_gamma 91.411(4) _cell_volume 1885.38(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5747 _cell_measurement_temperature 190(2) _cell_measurement_theta_max 29.1411 _cell_measurement_theta_min 3.6768 _exptl_absorpt_coefficient_mu 2.525 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.49085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 924 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_unetI/netI 0.0400 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 20535 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.21 _diffrn_reflns_theta_min 3.68 _diffrn_ambient_temperature 190(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.853 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0640265000 _diffrn_orient_matrix_UB_12 0.0050437000 _diffrn_orient_matrix_UB_13 0.0186042000 _diffrn_orient_matrix_UB_21 0.0322817000 _diffrn_orient_matrix_UB_22 0.0310079000 _diffrn_orient_matrix_UB_23 0.0445552000 _diffrn_orient_matrix_UB_31 -0.0091769000 _diffrn_orient_matrix_UB_32 0.0481248000 _diffrn_orient_matrix_UB_33 -0.0092424000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6488 _reflns_number_total 8725 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.984 _refine_diff_density_min -1.756 _refine_diff_density_rms 0.102 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 436 _refine_ls_number_reflns 8725 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0425 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.4228P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1116 _refine_ls_wR_factor_ref 0.1207 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 3. Others Sof(O2A)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)=Sof(H31E)= Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(O3A)=Sof(C22A)= Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(C24A)=Sof(H24A)= Sof(C23A)=Sof(H23A)=Sof(I3A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1) Sof(I3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C24B)=Sof(H24B)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I2 I 0.99666(4) 0.13778(3) 0.97431(2) 0.05438(11) Uani 1 1 d . . . I1 I 1.71037(3) 0.03970(3) 0.12877(2) 0.05312(11) Uani 1 1 d . . . I3B I 0.5126(6) 0.9598(4) 0.3324(5) 0.0886(12) Uani 0.539(10) 1 d A 1 . O2A O 0.9645(16) 0.285(2) 0.6378(19) 0.031(3) Uani 0.461(10) 1 d A 2 . C9 C 1.2946(4) 0.1155(3) 0.1864(3) 0.0360(9) Uani 1 1 d . . . H9 H 1.2069 0.0875 0.1558 0.043 Uiso 1 1 calc . . R O3B O 0.6835(16) 0.5277(18) 0.3607(15) 0.033(3) Uani 0.539(10) 1 d A 1 . C8 C 1.3067(4) 0.1992(3) 0.2717(3) 0.0348(8) Uani 1 1 d . . . C15 C 0.9482(5) 0.2497(3) 0.7093(3) 0.0398(9) Uani 1 1 d . . . C19 C 0.8569(4) 0.1632(3) 0.8053(3) 0.0425(10) Uani 1 1 d . . . H19 H 0.7839 0.1253 0.8191 0.051 Uiso 1 1 calc A . R C18 C 0.9760(4) 0.1884(3) 0.8607(3) 0.0374(9) Uani 1 1 d A . . C10 C 1.4097(4) 0.0727(3) 0.1457(3) 0.0408(9) Uani 1 1 d . . . H10 H 1.4012 0.0150 0.0872 0.049 Uiso 1 1 calc . . R C12 C 1.5507(4) 0.1975(3) 0.2742(3) 0.0415(9) Uani 1 1 d . . . H12 H 1.6385 0.2255 0.3045 0.050 Uiso 1 1 calc . . R C13 C 1.4358(4) 0.2400(3) 0.3141(3) 0.0416(10) Uani 1 1 d . . . H13 H 1.4447 0.2988 0.3721 0.050 Uiso 1 1 calc . . R C20 C 0.8422(5) 0.1931(3) 0.7282(3) 0.0430(10) Uani 1 1 d A . . H20 H 0.7597 0.1748 0.6887 0.052 Uiso 1 1 calc . . R C22B C 0.6606(15) 0.6262(11) 0.3616(9) 0.036(4) Uiso 0.539(10) 1 d A 1 . C27B C 0.7031(11) 0.7246(7) 0.4295(8) 0.038(3) Uiso 0.539(10) 1 d A 1 . H27B H 0.7609 0.7288 0.4827 0.045 Uiso 0.539(10) 1 calc A 1 R C23B C 0.5845(13) 0.6211(10) 0.2825(9) 0.044(4) Uiso 0.539(10) 1 d A 1 . H23B H 0.5660 0.5527 0.2337 0.053 Uiso 0.539(10) 1 calc A 1 R C11 C 1.5368(4) 0.1130(3) 0.1893(3) 0.0385(9) Uani 1 1 d . . . C16 C 1.0684(5) 0.2757(3) 0.7670(3) 0.0451(10) Uani 1 1 d A . . H16 H 1.1409 0.3152 0.7544 0.054 Uiso 1 1 calc . . R C25B C 0.5738(8) 0.8075(7) 0.3386(7) 0.035(2) Uiso 0.539(10) 1 d A 1 . C26B C 0.6579(9) 0.8175(7) 0.4172(7) 0.039(2) Uiso 0.539(10) 1 d A 1 . H26B H 0.6846 0.8871 0.4623 0.046 Uiso 0.539(10) 1 calc A 1 R O1 O 1.1994(3) 0.2465(2) 0.31966(19) 0.0394(6) Uani 1 1 d A . . C2 C 0.9434(4) 0.2251(3) 0.4204(3) 0.0344(8) Uani 1 1 d . . . C1 C 0.9703(4) 0.2660(3) 0.3518(3) 0.0348(8) Uani 1 1 d A . . C28 C 1.0063(4) 0.1227(3) 0.4224(3) 0.0366(9) Uani 1 1 d A . . H28A H 1.0268 0.1295 0.4877 0.044 Uiso 1 1 calc . . R H28B H 1.0935 0.1152 0.3938 0.044 Uiso 1 1 calc . . R C21B C 0.7821(13) 0.5300(14) 0.4373(13) 0.033(3) Uani 0.539(10) 1 d A 1 . H21A H 0.7420 0.5623 0.4970 0.039 Uiso 0.539(10) 1 calc A 1 R H21B H 0.8649 0.5747 0.4390 0.039 Uiso 0.539(10) 1 calc A 1 R C7 C 1.0625(4) 0.2069(3) 0.2789(3) 0.0357(8) Uani 1 1 d . . . H7A H 1.0510 0.1277 0.2631 0.043 Uiso 1 1 calc A . R H7B H 1.0420 0.2229 0.2219 0.043 Uiso 1 1 calc . . R C32 C 0.9486(4) 0.4095(3) 0.2792(3) 0.0396(9) Uani 1 1 d A . . H32A H 1.0385 0.3867 0.2573 0.047 Uiso 1 1 calc . . R H32B H 0.9527 0.4896 0.3061 0.047 Uiso 1 1 calc . . R C6 C 0.9198(4) 0.3653(3) 0.3538(3) 0.0352(8) Uani 1 1 d . . . C33 C 0.8400(5) 0.3700(4) 0.1972(3) 0.0496(11) Uani 1 1 d . . . H33A H 0.8627 0.3998 0.1505 0.074 Uiso 1 1 calc A . GR H33B H 0.7511 0.3941 0.2183 0.074 Uiso 1 1 calc . . GR H33C H 0.8362 0.2907 0.1699 0.074 Uiso 1 1 calc . . GR C3B C 0.8388(11) 0.2724(11) 0.4828(9) 0.024(2) Uani 0.539(10) 1 d A 1 . C29 C 0.9143(5) 0.0202(3) 0.3715(3) 0.0487(11) Uani 1 1 d . . . H29A H 0.9007 0.0090 0.3055 0.073 Uiso 1 1 calc A . GR H29B H 0.8260 0.0284 0.3975 0.073 Uiso 1 1 calc . . GR H29C H 0.9573 -0.0423 0.3791 0.073 Uiso 1 1 calc . . GR C5B C 0.8182(10) 0.4172(11) 0.4230(9) 0.024(2) Uani 0.539(10) 1 d A 1 . C14B C 0.8128(12) 0.2336(8) 0.5604(7) 0.033(2) Uani 0.539(10) 1 d A 1 . H14A H 0.7252 0.2589 0.5852 0.039 Uiso 0.539(10) 1 calc A 1 R H14B H 0.8090 0.1534 0.5378 0.039 Uiso 0.539(10) 1 calc A 1 R C4A C 0.8434(12) 0.3911(7) 0.4996(7) 0.029(2) Uani 0.461(10) 1 d A 2 . C30A C 0.7689(9) 0.4558(6) 0.5813(6) 0.033(2) Uani 0.461(10) 1 d A 2 . H30A H 0.7928 0.4320 0.6337 0.039 Uiso 0.461(10) 1 calc A 2 R H30B H 0.7981 0.5335 0.6011 0.039 Uiso 0.461(10) 1 calc A 2 R C30B C 0.6633(11) 0.4119(8) 0.5423(8) 0.033(2) Uani 0.539(10) 1 d A 1 . H30C H 0.6060 0.4527 0.5125 0.039 Uiso 0.539(10) 1 calc A 1 R H30D H 0.6058 0.3501 0.5431 0.039 Uiso 0.539(10) 1 calc A 1 R C31B C 0.7047(8) 0.4850(6) 0.6411(6) 0.043(2) Uani 0.539(10) 1 d A 1 . H31A H 0.7615 0.5470 0.6418 0.065 Uiso 0.539(10) 1 calc A 1 GR H31B H 0.7564 0.4446 0.6731 0.065 Uiso 0.539(10) 1 calc A 1 GR H31C H 0.6230 0.5108 0.6727 0.065 Uiso 0.539(10) 1 calc A 1 GR C17 C 1.0835(5) 0.2449(3) 0.8420(3) 0.0452(10) Uani 1 1 d . . . H17 H 1.1666 0.2619 0.8809 0.054 Uiso 1 1 calc A . R C4B C 0.7774(10) 0.3674(6) 0.4825(5) 0.0254(17) Uani 0.539(10) 1 d A 1 . C24B C 0.5347(11) 0.7102(8) 0.2714(8) 0.050(3) Uiso 0.539(10) 1 d A 1 . H24B H 0.4748 0.7048 0.2189 0.061 Uiso 0.539(10) 1 calc A 1 R C31A C 0.6190(14) 0.4418(12) 0.5573(11) 0.048(3) Uani 0.461(10) 1 d A 2 . H31D H 0.5955 0.4641 0.5046 0.071 Uiso 0.461(10) 1 calc A 2 GR H31E H 0.5733 0.4866 0.6107 0.071 Uiso 0.461(10) 1 calc A 2 GR H31F H 0.5894 0.3655 0.5408 0.071 Uiso 0.461(10) 1 calc A 2 GR C3A C 0.8860(13) 0.2875(15) 0.4946(11) 0.028(3) Uani 0.461(10) 1 d A 2 . C5A C 0.8692(12) 0.4283(13) 0.4293(11) 0.024(3) Uani 0.461(10) 1 d A 2 . C21A C 0.8300(14) 0.5418(16) 0.4382(14) 0.026(3) Uani 0.461(10) 1 d A 2 . H21C H 0.8066 0.5816 0.5020 0.031 Uiso 0.461(10) 1 calc A 2 R H21D H 0.9088 0.5815 0.4267 0.031 Uiso 0.461(10) 1 calc A 2 R O3A O 0.7196(18) 0.5379(19) 0.3754(16) 0.031(3) Uani 0.461(10) 1 d A 2 . C22A C 0.6634(18) 0.6384(12) 0.3733(9) 0.038(5) Uiso 0.461(10) 1 d A 2 . C27A C 0.6898(12) 0.7335(7) 0.4473(9) 0.030(3) Uiso 0.461(10) 1 d A 2 . H27A H 0.7378 0.7323 0.5023 0.036 Uiso 0.461(10) 1 calc A 2 R C26A C 0.6487(9) 0.8315(7) 0.4445(7) 0.027(2) Uiso 0.461(10) 1 d A 2 . H26A H 0.6735 0.8972 0.4952 0.032 Uiso 0.461(10) 1 calc A 2 R C25A C 0.5719(8) 0.8322(7) 0.3676(6) 0.022(2) Uiso 0.461(10) 1 d A 2 . C24A C 0.5367(10) 0.7374(8) 0.2922(7) 0.028(2) Uiso 0.461(10) 1 d A 2 . H24A H 0.4857 0.7392 0.2383 0.034 Uiso 0.461(10) 1 calc A 2 R C23A C 0.5777(15) 0.6393(11) 0.2970(10) 0.043(4) Uiso 0.461(10) 1 d A 2 . H23A H 0.5475 0.5730 0.2485 0.051 Uiso 0.461(10) 1 calc A 2 R I3A I 0.5059(7) 0.9737(4) 0.3547(4) 0.0654(8) Uani 0.461(10) 1 d A 2 . C14A C 0.8556(13) 0.2438(12) 0.5684(11) 0.031(4) Uiso 0.461(10) 1 d A 2 . H14C H 0.7679 0.2688 0.5932 0.037 Uiso 0.461(10) 1 calc A 2 R H14D H 0.8512 0.1636 0.5434 0.037 Uiso 0.461(10) 1 calc A 2 R O2B O 0.9241(14) 0.278(2) 0.6309(18) 0.042(4) Uani 0.539(10) 1 d A 1 . 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 I2 0.0672(2) 0.0701(2) 0.03718(17) 0.03095(15) 0.01250(15) 0.01425(16) I1 0.04213(17) 0.0716(2) 0.04200(18) 0.01580(15) 0.00576(13) 0.00755(14) I3B 0.0453(7) 0.091(2) 0.176(4) 0.107(2) -0.005(2) 0.0055(16) O2A 0.028(7) 0.045(6) 0.035(5) 0.031(5) 0.002(7) -0.003(7) C9 0.036(2) 0.038(2) 0.031(2) 0.0106(16) -0.0055(16) 0.0019(16) O3B 0.030(7) 0.034(6) 0.034(7) 0.016(5) -0.020(4) -0.005(5) C8 0.040(2) 0.0327(19) 0.033(2) 0.0142(16) -0.0007(17) 0.0032(16) C15 0.055(3) 0.035(2) 0.036(2) 0.0188(17) 0.016(2) 0.0096(18) C19 0.042(2) 0.052(2) 0.046(2) 0.031(2) 0.011(2) 0.0039(18) C18 0.048(2) 0.039(2) 0.033(2) 0.0188(17) 0.0155(18) 0.0119(17) C10 0.045(2) 0.046(2) 0.028(2) 0.0101(17) -0.0022(18) 0.0022(18) C12 0.040(2) 0.041(2) 0.040(2) 0.0131(18) -0.0055(18) -0.0061(17) C13 0.043(2) 0.034(2) 0.039(2) 0.0060(17) -0.0058(19) -0.0050(17) C20 0.045(2) 0.050(2) 0.044(2) 0.030(2) 0.0039(19) 0.0052(19) C11 0.038(2) 0.046(2) 0.035(2) 0.0188(18) 0.0030(17) 0.0005(17) C16 0.054(3) 0.041(2) 0.043(2) 0.0171(19) 0.014(2) -0.0027(19) O1 0.0356(14) 0.0363(14) 0.0386(15) 0.0059(12) -0.0025(12) -0.0016(11) C2 0.043(2) 0.0267(18) 0.034(2) 0.0115(15) -0.0009(17) 0.0056(15) C1 0.042(2) 0.0272(18) 0.032(2) 0.0076(15) -0.0008(17) 0.0028(16) C28 0.040(2) 0.0313(19) 0.039(2) 0.0150(16) -0.0018(18) 0.0063(16) C21B 0.031(7) 0.028(6) 0.038(6) 0.013(4) -0.002(6) 0.002(6) C7 0.036(2) 0.0329(19) 0.034(2) 0.0088(16) -0.0058(17) -0.0016(16) C32 0.043(2) 0.043(2) 0.040(2) 0.0234(18) 0.0032(18) 0.0044(17) C6 0.046(2) 0.0319(19) 0.031(2) 0.0154(16) 0.0009(17) 0.0019(16) C33 0.057(3) 0.063(3) 0.033(2) 0.023(2) 0.003(2) 0.013(2) C3B 0.021(6) 0.020(5) 0.031(5) 0.011(4) -0.004(5) -0.001(4) C29 0.054(3) 0.029(2) 0.060(3) 0.0143(19) -0.003(2) 0.0043(18) C5B 0.018(5) 0.025(4) 0.027(4) 0.006(3) -0.002(5) 0.001(5) C14B 0.030(5) 0.034(5) 0.038(5) 0.020(4) -0.005(4) 0.000(4) C4A 0.026(5) 0.021(4) 0.036(5) 0.007(4) -0.001(4) -0.003(4) C30A 0.040(5) 0.028(4) 0.032(5) 0.013(3) 0.005(4) 0.001(3) C30B 0.034(6) 0.030(5) 0.037(5) 0.014(4) 0.010(4) 0.015(4) C31B 0.043(4) 0.038(4) 0.048(5) 0.012(4) 0.014(4) 0.000(3) C17 0.046(2) 0.049(2) 0.040(2) 0.0162(19) 0.005(2) -0.0014(19) C4B 0.024(4) 0.025(4) 0.029(4) 0.013(3) -0.003(3) -0.001(3) C31A 0.038(8) 0.051(9) 0.049(8) 0.013(7) 0.005(6) 0.005(5) C3A 0.023(7) 0.036(6) 0.025(5) 0.015(4) -0.012(5) -0.012(6) C5A 0.016(6) 0.032(5) 0.031(5) 0.021(4) -0.002(5) 0.003(5) C21A 0.028(7) 0.025(5) 0.025(5) 0.013(4) -0.005(6) -0.003(6) O3A 0.035(9) 0.022(4) 0.028(7) 0.005(4) -0.019(6) -0.003(6) I3A 0.0524(15) 0.0514(8) 0.1077(14) 0.0511(10) -0.0122(10) 0.0073(7) O2B 0.036(8) 0.047(4) 0.049(6) 0.028(4) 0.003(7) -0.012(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 I2 C18 2.101(4) . ? I1 C11 2.104(4) . ? I3B C25B 2.154(10) . ? O2A C15 1.37(2) . ? O2A C14A 1.41(2) . ? C9 H9 0.9500 . ? C9 C8 1.382(5) . ? C9 C10 1.375(6) . ? O3B C22B 1.33(3) . ? O3B C21B 1.467(19) . ? C8 C13 1.387(6) . ? C8 O1 1.374(5) . ? C15 C20 1.381(6) . ? C15 C16 1.385(7) . ? C15 O2B 1.41(2) . ? C19 H19 0.9500 . ? C19 C18 1.359(6) . ? C19 C20 1.390(6) . ? C18 C17 1.392(6) . ? C10 H10 0.9500 . ? C10 C11 1.374(6) . ? C12 H12 0.9500 . ? C12 C13 1.368(6) . ? C12 C11 1.383(6) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C22B C27B 1.379(11) . ? C22B C23B 1.369(11) . ? C27B H27B 0.9500 . ? C27B C26B 1.391(10) . ? C23B H23B 0.9500 . ? C23B C24B 1.352(11) . ? C16 H16 0.9500 . ? C16 C17 1.366(6) . ? C25B C26B 1.385(10) . ? C25B C24B 1.358(10) . ? C26B H26B 0.9500 . ? O1 C7 1.445(5) . ? C2 C1 1.400(6) . ? C2 C28 1.516(5) . ? C2 C3B 1.465(13) . ? C2 C3A 1.330(18) . ? C1 C7 1.509(5) . ? C1 C6 1.410(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.531(6) . ? C21B H21A 0.9900 . ? C21B H21B 0.9900 . ? C21B C5B 1.49(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.517(5) . ? C32 C33 1.525(6) . ? C6 C5B 1.517(12) . ? C6 C5A 1.314(16) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.508(18) . ? C3B C4B 1.412(15) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.394(16) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C14B O2B 1.44(2) . ? C4A C30A 1.509(12) . ? C4A C3A 1.42(2) . ? C4A C5A 1.388(18) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.486(16) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.507(15) . ? C30B C4B 1.508(13) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C24B H24B 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C3A C14A 1.51(2) . ? C5A C21A 1.52(3) . ? C21A H21C 0.9900 . ? C21A H21D 0.9900 . ? C21A O3A 1.39(2) . ? O3A C22A 1.47(3) . ? C22A C27A 1.367(12) . ? C22A C23A 1.405(12) . ? C27A H27A 0.9500 . ? C27A C26A 1.385(10) . ? C26A H26A 0.9500 . ? C26A C25A 1.366(10) . ? C25A C24A 1.387(10) . ? C25A I3A 2.073(10) . ? C24A H24A 0.9500 . ? C24A C23A 1.398(12) . ? C23A H23A 0.9500 . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? 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 C15 O2A C14A 110.1(14) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C10 C9 C8 119.9(4) . . ? C22B O3B C21B 112.3(14) . . ? C9 C8 C13 119.0(4) . . ? O1 C8 C9 125.0(3) . . ? O1 C8 C13 116.0(3) . . ? O2A C15 C20 132.4(8) . . ? O2A C15 C16 107.8(8) . . ? O2A C15 O2B 16.7(9) . . ? C20 C15 C16 119.8(4) . . ? C20 C15 O2B 116.1(7) . . ? C16 C15 O2B 124.2(7) . . ? C18 C19 H19 120.1 . . ? C18 C19 C20 119.8(4) . . ? C20 C19 H19 120.1 . . ? C19 C18 I2 118.8(3) . . ? C19 C18 C17 120.9(4) . . ? C17 C18 I2 120.3(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H10 119.8 . . ? C13 C12 H12 120.5 . . ? C13 C12 C11 118.9(4) . . ? C11 C12 H12 120.5 . . ? C8 C13 H13 119.3 . . ? C12 C13 C8 121.4(4) . . ? C12 C13 H13 119.3 . . ? C15 C20 C19 119.7(4) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? O3B C22B C27B 128.2(12) . . ? O3B C22B C23B 110.9(12) . . ? C23B C22B C27B 120.9(12) . . ? C22B C27B H27B 121.3 . . ? C22B C27B C26B 117.4(10) . . ? C26B C27B H27B 121.3 . . ? C22B C23B H23B 118.9 . . ? C24B C23B C22B 122.1(12) . . ? C24B C23B H23B 118.9 . . ? C10 C11 I1 119.3(3) . . ? C10 C11 C12 120.4(4) . . ? C12 C11 I1 120.2(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.5(4) . . ? C17 C16 H16 119.7 . . ? C26B C25B I3B 114.0(6) . . ? C24B C25B I3B 123.4(7) . . ? C24B C25B C26B 122.6(8) . . ? C27B C26B H26B 120.3 . . ? C25B C26B C27B 119.3(9) . . ? C25B C26B H26B 120.3 . . ? C8 O1 C7 118.4(3) . . ? C1 C2 C28 120.7(3) . . ? C1 C2 C3B 119.6(6) . . ? C3B C2 C28 119.1(6) . . ? C3A C2 C1 119.1(8) . . ? C3A C2 C28 118.7(8) . . ? C3A C2 C3B 19.7(5) . . ? C2 C1 C7 119.4(3) . . ? C2 C1 C6 120.7(3) . . ? C6 C1 C7 119.8(4) . . ? C2 C28 H28A 108.9 . . ? C2 C28 H28B 108.9 . . ? C2 C28 C29 113.2(3) . . ? H28A C28 H28B 107.7 . . ? C29 C28 H28A 108.9 . . ? C29 C28 H28B 108.9 . . ? O3B C21B H21A 109.9 . . ? O3B C21B H21B 109.9 . . ? O3B C21B C5B 108.8(15) . . ? H21A C21B H21B 108.3 . . ? C5B C21B H21A 109.9 . . ? C5B C21B H21B 109.9 . . ? O1 C7 C1 105.4(3) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.9 . . ? C6 C32 H32A 109.2 . . ? C6 C32 H32B 109.2 . . ? C6 C32 C33 112.1(4) . . ? C33 C32 H32A 109.2 . . ? C33 C32 H32B 109.2 . . ? C1 C6 C32 120.7(4) . . ? C1 C6 C5B 118.0(6) . . ? C32 C6 C5B 120.6(6) . . ? C5A C6 C1 118.7(7) . . ? C5A C6 C32 119.5(7) . . ? C5A C6 C5B 19.2(6) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 120.6(10) . . ? C4B C3B C2 120.7(10) . . ? C4B C3B C14B 117.7(10) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C21B C5B C6 118.5(11) . . ? C4B C5B C21B 120.3(11) . . ? C4B C5B C6 120.3(10) . . ? C3B C14B H14A 110.4 . . ? C3B C14B H14B 110.4 . . ? H14A C14B H14B 108.6 . . ? O2B C14B C3B 106.6(12) . . ? O2B C14B H14A 110.4 . . ? O2B C14B H14B 110.4 . . ? C3A C4A C30A 118.1(10) . . ? C5A C4A C30A 122.4(9) . . ? C5A C4A C3A 119.5(11) . . ? C4A C30A H30A 109.4 . . ? C4A C30A H30B 109.4 . . ? H30A C30A H30B 108.0 . . ? C31A C30A C4A 111.1(10) . . ? C31A C30A H30A 109.4 . . ? C31A C30A H30B 109.4 . . ? H30C C30B H30D 107.3 . . ? C31B C30B H30C 108.2 . . ? C31B C30B H30D 108.2 . . ? C31B C30B C4B 116.5(9) . . ? C4B C30B H30C 108.2 . . ? C4B C30B H30D 108.2 . . ? C18 C17 H17 120.3 . . ? C16 C17 C18 119.3(4) . . ? C16 C17 H17 120.3 . . ? C3B C4B C30B 120.6(8) . . ? C5B C4B C3B 119.5(9) . . ? C5B C4B C30B 119.8(8) . . ? C23B C24B C25B 117.3(10) . . ? C23B C24B H24B 121.4 . . ? C25B C24B H24B 121.4 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 119.7(13) . . ? C2 C3A C14A 119.5(15) . . ? C4A C3A C14A 120.6(13) . . ? C6 C5A C4A 121.1(12) . . ? C6 C5A C21A 119.9(13) . . ? C4A C5A C21A 118.9(13) . . ? C5A C21A H21C 109.4 . . ? C5A C21A H21D 109.4 . . ? H21C C21A H21D 108.0 . . ? O3A C21A C5A 111.2(16) . . ? O3A C21A H21C 109.4 . . ? O3A C21A H21D 109.4 . . ? C21A O3A C22A 120.3(17) . . ? C27A C22A O3A 120.5(12) . . ? C27A C22A C23A 118.2(13) . . ? C23A C22A O3A 121.3(12) . . ? C22A C27A H27A 119.0 . . ? C22A C27A C26A 122.0(11) . . ? C26A C27A H27A 119.0 . . ? C27A C26A H26A 120.5 . . ? C25A C26A C27A 118.9(9) . . ? C25A C26A H26A 120.5 . . ? C26A C25A C24A 121.4(8) . . ? C26A C25A I3A 122.5(6) . . ? C24A C25A I3A 116.0(6) . . ? C25A C24A H24A 120.7 . . ? C25A C24A C23A 118.6(9) . . ? C23A C24A H24A 120.7 . . ? C22A C23A H23A 119.9 . . ? C24A C23A C22A 120.2(12) . . ? C24A C23A H23A 119.9 . . ? O2A C14A C3A 104.9(13) . . ? O2A C14A H14C 110.8 . . ? O2A C14A H14D 110.8 . . ? C3A C14A H14C 110.8 . . ? C3A C14A H14D 110.8 . . ? H14C C14A H14D 108.9 . . ? C15 O2B C14B 124.4(14) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 C18 C17 C16 179.1(3) . . . . ? I3B C25B C26B C27B 179.3(8) . . . . ? I3B C25B C24B C23B 177.7(9) . . . . ? O2A C15 C20 C19 177.0(17) . . . . ? O2A C15 C16 C17 -176.7(13) . . . . ? O2A C15 O2B C14B 155(10) . . . . ? C9 C8 C13 C12 -1.6(6) . . . . ? C9 C8 O1 C7 0.0(5) . . . . ? C9 C10 C11 I1 176.5(3) . . . . ? C9 C10 C11 C12 -0.3(6) . . . . ? O3B C22B C27B C26B -175.7(17) . . . . ? O3B C22B C23B C24B 172.4(15) . . . . ? O3B C21B C5B C6 78.9(15) . . . . ? O3B C21B C5B C4B -111.6(16) . . . . ? C8 C9 C10 C11 -0.3(6) . . . . ? C8 O1 C7 C1 174.1(3) . . . . ? C15 O2A C14A C3A -179.5(17) . . . . ? C15 C16 C17 C18 -1.0(6) . . . . ? C19 C18 C17 C16 0.3(6) . . . . ? C18 C19 C20 C15 -0.9(6) . . . . ? C10 C9 C8 C13 1.3(6) . . . . ? C10 C9 C8 O1 -178.6(4) . . . . ? C13 C8 O1 C7 -179.8(4) . . . . ? C13 C12 C11 I1 -176.8(3) . . . . ? C13 C12 C11 C10 0.0(6) . . . . ? C20 C15 C16 C17 0.7(6) . . . . ? C20 C15 O2B C14B -14(3) . . . . ? C20 C19 C18 I2 -178.2(3) . . . . ? C20 C19 C18 C17 0.7(6) . . . . ? C22B O3B C21B C5B -171.3(15) . . . . ? C22B C27B C26B C25B -0.1(16) . . . . ? C22B C23B C24B C25B 6.1(19) . . . . ? C27B C22B C23B C24B -8(2) . . . . ? C23B C22B C27B C26B 4(2) . . . . ? C11 C12 C13 C8 1.0(6) . . . . ? C16 C15 C20 C19 0.3(6) . . . . ? C16 C15 O2B C14B 166.6(13) . . . . ? C26B C25B C24B C23B -1.8(16) . . . . ? O1 C8 C13 C12 178.2(4) . . . . ? C2 C1 C7 O1 -85.2(4) . . . . ? C2 C1 C6 C32 -179.8(4) . . . . ? C2 C1 C6 C5B -9.4(7) . . . . ? C2 C1 C6 C5A 12.4(8) . . . . ? C2 C3B C14B O2B 74.8(15) . . . . ? C2 C3B C4B C5B -0.8(13) . . . . ? C2 C3B C4B C30B 176.0(9) . . . . ? C2 C3A C14A O2A 98.7(16) . . . . ? C1 C2 C28 C29 -93.7(5) . . . . ? C1 C2 C3B C14B -176.9(7) . . . . ? C1 C2 C3B C4B -8.3(11) . . . . ? C1 C2 C3A C4A 4.8(12) . . . . ? C1 C2 C3A C14A 179.5(8) . . . . ? C1 C6 C5B C21B 169.7(9) . . . . ? C1 C6 C5B C4B 0.2(11) . . . . ? C1 C6 C5A C4A -11.1(13) . . . . ? C1 C6 C5A C21A 172.5(8) . . . . ? C28 C2 C1 C7 0.3(6) . . . . ? C28 C2 C1 C6 -175.4(3) . . . . ? C28 C2 C3B C14B 11.7(11) . . . . ? C28 C2 C3B C4B -179.7(6) . . . . ? C28 C2 C3A C4A 171.2(7) . . . . ? C28 C2 C3A C14A -14.1(12) . . . . ? C21B O3B C22B C27B -9(3) . . . . ? C21B O3B C22B C23B 171.1(16) . . . . ? C21B C5B C4B C3B -164.6(10) . . . . ? C21B C5B C4B C30B 18.5(15) . . . . ? C7 C1 C6 C32 4.5(6) . . . . ? C7 C1 C6 C5B 175.0(5) . . . . ? C7 C1 C6 C5A -163.2(7) . . . . ? C32 C6 C5B C21B -19.8(12) . . . . ? C32 C6 C5B C4B 170.7(7) . . . . ? C32 C6 C5A C4A -179.1(8) . . . . ? C32 C6 C5A C21A 4.5(13) . . . . ? C6 C1 C7 O1 90.5(4) . . . . ? C6 C5B C4B C3B 4.7(13) . . . . ? C6 C5B C4B C30B -172.2(9) . . . . ? C6 C5A C21A O3A 67.2(18) . . . . ? C33 C32 C6 C1 89.5(5) . . . . ? C33 C32 C6 C5B -80.6(6) . . . . ? C33 C32 C6 C5A -102.8(7) . . . . ? C3B C2 C1 C7 -171.0(6) . . . . ? C3B C2 C1 C6 13.4(7) . . . . ? C3B C2 C28 C29 77.6(7) . . . . ? C3B C2 C3A C4A -92(4) . . . . ? C3B C2 C3A C14A 83(4) . . . . ? C3B C14B O2B C15 -170.9(18) . . . . ? C5B C6 C5A C4A 82(3) . . . . ? C5B C6 C5A C21A -94(3) . . . . ? C14B C3B C4B C5B 168.1(9) . . . . ? C14B C3B C4B C30B -15.1(13) . . . . ? C4A C3A C14A O2A -86.7(17) . . . . ? C4A C5A C21A O3A -109.3(19) . . . . ? C30A C4A C3A C2 175.3(9) . . . . ? C30A C4A C3A C14A 0.7(15) . . . . ? C30A C4A C5A C6 -172.0(10) . . . . ? C30A C4A C5A C21A 4.5(16) . . . . ? C31B C30B C4B C3B 85.1(11) . . . . ? C31B C30B C4B C5B -98.1(11) . . . . ? C4B C3B C14B O2B -94.1(14) . . . . ? C24B C25B C26B C27B -1.1(15) . . . . ? C3A C2 C1 C7 166.4(6) . . . . ? C3A C2 C1 C6 -9.2(8) . . . . ? C3A C2 C28 C29 100.1(7) . . . . ? C3A C2 C3B C14B -83(4) . . . . ? C3A C2 C3B C4B 86(4) . . . . ? C3A C4A C30A C31A -97.0(11) . . . . ? C3A C4A C5A C6 6.9(15) . . . . ? C3A C4A C5A C21A -176.7(10) . . . . ? C5A C6 C5B C21B 72(3) . . . . ? C5A C6 C5B C4B -97(3) . . . . ? C5A C4A C30A C31A 81.8(13) . . . . ? C5A C4A C3A C2 -3.5(15) . . . . ? C5A C4A C3A C14A -178.2(10) . . . . ? C5A C21A O3A C22A 178.9(19) . . . . ? C21A O3A C22A C27A -19(3) . . . . ? C21A O3A C22A C23A 163(2) . . . . ? O3A C22A C27A C26A 174.1(17) . . . . ? O3A C22A C23A C24A -173.4(17) . . . . ? C22A C27A C26A C25A 4.3(18) . . . . ? C27A C22A C23A C24A 9(2) . . . . ? C27A C26A C25A C24A -1.2(14) . . . . ? C27A C26A C25A I3A -179.4(8) . . . . ? C26A C25A C24A C23A 2.0(15) . . . . ? C25A C24A C23A C22A -6(2) . . . . ? C23A C22A C27A C26A -8(2) . . . . ? I3A C25A C24A C23A -179.6(9) . . . . ? C14A O2A C15 C20 -8(3) . . . . ? C14A O2A C15 C16 169.3(14) . . . . ? C14A O2A C15 O2B -20(7) . . . . ? O2B C15 C20 C19 -179.0(13) . . . . ? O2B C15 C16 C17 179.9(14) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.010 0.500 0.500 407 37 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962437' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-ea-226K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-ea, 226 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 I3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 I3 O5' _chemical_formula_weight 946.40 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.9060(5) _cell_length_b 13.3034(6) _cell_length_c 15.5724(7) _cell_angle_alpha 111.092(4) _cell_angle_beta 94.353(4) _cell_angle_gamma 91.198(4) _cell_volume 1906.61(15) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5016 _cell_measurement_temperature 226(2) _cell_measurement_theta_max 29.0367 _cell_measurement_theta_min 3.6690 _exptl_absorpt_coefficient_mu 2.497 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58483 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 924 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_unetI/netI 0.0412 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 19109 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.10 _diffrn_reflns_theta_min 3.68 _diffrn_ambient_temperature 226(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.851 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0637517000 _diffrn_orient_matrix_UB_12 0.0049927000 _diffrn_orient_matrix_UB_13 0.0186312000 _diffrn_orient_matrix_UB_21 0.0319259000 _diffrn_orient_matrix_UB_22 0.0306936000 _diffrn_orient_matrix_UB_23 0.0444056000 _diffrn_orient_matrix_UB_31 -0.0093331000 _diffrn_orient_matrix_UB_32 0.0480352000 _diffrn_orient_matrix_UB_33 -0.0091401000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6215 _reflns_number_total 8720 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 2.105 _refine_diff_density_min -1.572 _refine_diff_density_rms 0.102 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 421 _refine_ls_number_reflns 8720 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0471 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.1122P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1258 _refine_ls_wR_factor_ref 0.1363 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Others Sof(O2A)=Sof(O3A)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)= Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)= Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(C24A)=Sof(H24A)= Sof(C23A)=Sof(H23A)=Sof(I3A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1) Sof(I3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C24B)=Sof(H24B)=Sof(O3B)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I2 I 0.99461(4) 0.13555(3) 0.97237(2) 0.06206(13) Uani 1 1 d . . . I1 I 1.70972(4) 0.04197(3) 0.12915(2) 0.06126(13) Uani 1 1 d . . . I3B I 0.5142(6) 0.9570(5) 0.3309(6) 0.0929(13) Uani 0.513(12) 1 d A 1 . O2A O 0.959(2) 0.287(2) 0.6423(16) 0.035(3) Uani 0.487(12) 1 d A 2 . C9 C 1.2957(4) 0.1169(3) 0.1863(3) 0.0402(10) Uani 1 1 d . . . H9 H 1.2097 0.0895 0.1559 0.048 Uiso 1 1 calc . . R O3A O 0.7185(15) 0.5358(15) 0.3675(13) 0.043(4) Uiso 0.487(12) 1 d A 2 . C8 C 1.3066(4) 0.2003(3) 0.2721(3) 0.0368(9) Uani 1 1 d . . . C15 C 0.9470(5) 0.2483(3) 0.7082(3) 0.0431(10) Uani 1 1 d . . . C19 C 0.8546(5) 0.1611(4) 0.8032(3) 0.0488(11) Uani 1 1 d . . . H19 H 0.7825 0.1241 0.8169 0.059 Uiso 1 1 calc A . R C18 C 0.9745(5) 0.1857(3) 0.8589(3) 0.0442(10) Uani 1 1 d A . . C10 C 1.4100(5) 0.0748(4) 0.1463(3) 0.0463(11) Uani 1 1 d . . . H10 H 1.4024 0.0182 0.0884 0.056 Uiso 1 1 calc . . R C12 C 1.5483(5) 0.1981(4) 0.2745(3) 0.0470(11) Uani 1 1 d . . . H12 H 1.6345 0.2259 0.3041 0.056 Uiso 1 1 calc . . R C13 C 1.4348(5) 0.2397(4) 0.3145(3) 0.0473(11) Uani 1 1 d . . . H13 H 1.4434 0.2966 0.3722 0.057 Uiso 1 1 calc . . R C20 C 0.8410(5) 0.1914(4) 0.7266(3) 0.0496(11) Uani 1 1 d A . . H20 H 0.7603 0.1733 0.6873 0.060 Uiso 1 1 calc . . R C22B C 0.6613(17) 0.6259(12) 0.3610(9) 0.042(5) Uiso 0.513(12) 1 d A 1 . C27B C 0.7009(15) 0.7232(8) 0.4268(9) 0.047(4) Uiso 0.513(12) 1 d A 1 . H27B H 0.7569 0.7271 0.4795 0.056 Uiso 0.513(12) 1 calc A 1 R C23B C 0.5869(14) 0.6210(11) 0.2831(10) 0.046(4) Uiso 0.513(12) 1 d A 1 . H23B H 0.5686 0.5538 0.2350 0.055 Uiso 0.513(12) 1 calc A 1 R C11 C 1.5358(5) 0.1145(3) 0.1899(3) 0.0414(10) Uani 1 1 d . . . C16 C 1.0668(5) 0.2741(4) 0.7654(3) 0.0506(11) Uani 1 1 d A . . H16 H 1.1383 0.3128 0.7528 0.061 Uiso 1 1 calc . . R C25B C 0.5743(9) 0.8076(8) 0.3392(7) 0.035(2) Uiso 0.513(12) 1 d A 1 . C26B C 0.6587(11) 0.8158(8) 0.4158(8) 0.042(3) Uiso 0.513(12) 1 d A 1 . H26B H 0.6871 0.8838 0.4600 0.050 Uiso 0.513(12) 1 calc A 1 R O1 O 1.1989(3) 0.2470(2) 0.3198(2) 0.0443(7) Uani 1 1 d A . . C2 C 0.9445(5) 0.2260(3) 0.4206(3) 0.0398(10) Uani 1 1 d . . . C1 C 0.9721(4) 0.2669(3) 0.3521(3) 0.0375(9) Uani 1 1 d A . . C28 C 1.0067(5) 0.1224(3) 0.4219(3) 0.0433(10) Uani 1 1 d A . . H28A H 1.0922 0.1141 0.3928 0.052 Uiso 1 1 calc . . R H28B H 1.0275 0.1286 0.4862 0.052 Uiso 1 1 calc . . R C21B C 0.7838(14) 0.5308(8) 0.4389(7) 0.032(2) Uani 0.513(12) 1 d A 1 . H21A H 0.7473 0.5622 0.4991 0.039 Uiso 0.513(12) 1 calc A 1 R H21B H 0.8648 0.5745 0.4391 0.039 Uiso 0.513(12) 1 calc A 1 R C7 C 1.0635(5) 0.2082(3) 0.2798(3) 0.0409(10) Uani 1 1 d . . . H7A H 1.0523 0.1301 0.2645 0.049 Uiso 1 1 calc A . R H7B H 1.0433 0.2237 0.2234 0.049 Uiso 1 1 calc . . R C32 C 0.9489(5) 0.4104(4) 0.2801(3) 0.0449(10) Uani 1 1 d A . . H32A H 0.9525 0.4894 0.3068 0.054 Uiso 1 1 calc . . R H32B H 1.0378 0.3882 0.2586 0.054 Uiso 1 1 calc . . R C6 C 0.9206(5) 0.3661(3) 0.3550(3) 0.0386(9) Uani 1 1 d . . . C33 C 0.8431(6) 0.3724(4) 0.1984(3) 0.0567(13) Uani 1 1 d . . . H33A H 0.8677 0.4008 0.1522 0.085 Uiso 1 1 calc A . GR H33B H 0.7556 0.3977 0.2186 0.085 Uiso 1 1 calc . . GR H33C H 0.8381 0.2942 0.1721 0.085 Uiso 1 1 calc . . GR C3B C 0.8378(11) 0.2724(11) 0.4830(11) 0.026(3) Uani 0.513(12) 1 d A 1 . C29 C 0.9140(6) 0.0221(3) 0.3718(4) 0.0560(13) Uani 1 1 d . . . H29A H 0.9006 0.0112 0.3067 0.084 Uiso 1 1 calc A . GR H29B H 0.8272 0.0314 0.3979 0.084 Uiso 1 1 calc . . GR H29C H 0.9552 -0.0403 0.3791 0.084 Uiso 1 1 calc . . GR C5B C 0.8213(12) 0.4159(7) 0.4228(6) 0.027(2) Uani 0.513(12) 1 d A 1 . C14B C 0.8190(18) 0.2345(10) 0.5597(9) 0.030(3) Uani 0.513(12) 1 d A 1 . H14A H 0.7340 0.2595 0.5866 0.036 Uiso 0.513(12) 1 calc A 1 R H14B H 0.8149 0.1554 0.5370 0.036 Uiso 0.513(12) 1 calc A 1 R C4A C 0.8420(13) 0.3896(8) 0.4998(7) 0.033(2) Uani 0.487(12) 1 d A 2 . C30A C 0.7661(10) 0.4560(7) 0.5817(7) 0.041(3) Uani 0.487(12) 1 d A 2 . H30A H 0.7874 0.4325 0.6339 0.049 Uiso 0.487(12) 1 calc A 2 R H30B H 0.7950 0.5324 0.6011 0.049 Uiso 0.487(12) 1 calc A 2 R C30B C 0.6630(12) 0.4129(9) 0.5420(9) 0.037(3) Uani 0.513(12) 1 d A 1 . H30C H 0.6074 0.4542 0.5131 0.045 Uiso 0.513(12) 1 calc A 1 R H30D H 0.6055 0.3523 0.5426 0.045 Uiso 0.513(12) 1 calc A 1 R C31B C 0.7052(10) 0.4845(7) 0.6409(6) 0.047(3) Uani 0.513(12) 1 d A 1 . H31A H 0.7686 0.5416 0.6418 0.071 Uiso 0.513(12) 1 calc A 1 GR H31B H 0.7483 0.4420 0.6734 0.071 Uiso 0.513(12) 1 calc A 1 GR H31C H 0.6259 0.5160 0.6710 0.071 Uiso 0.513(12) 1 calc A 1 GR C17 C 1.0806(5) 0.2429(4) 0.8408(3) 0.0512(11) Uani 1 1 d . . . H17 H 1.1615 0.2602 0.8799 0.061 Uiso 1 1 calc A . R C4B C 0.7778(12) 0.3676(8) 0.4819(7) 0.031(2) Uani 0.513(12) 1 d A 1 . C24B C 0.5387(12) 0.7100(9) 0.2731(9) 0.050(3) Uiso 0.513(12) 1 d A 1 . H24B H 0.4808 0.7047 0.2208 0.059 Uiso 0.513(12) 1 calc A 1 R C31A C 0.6160(16) 0.4415(15) 0.5547(13) 0.067(4) Uani 0.487(12) 1 d A 2 . H31D H 0.5935 0.4752 0.5099 0.101 Uiso 0.487(12) 1 calc A 2 GR H31E H 0.5679 0.4750 0.6090 0.101 Uiso 0.487(12) 1 calc A 2 GR H31F H 0.5899 0.3652 0.5276 0.101 Uiso 0.487(12) 1 calc A 2 GR C3A C 0.8856(13) 0.2867(14) 0.4931(11) 0.029(3) Uani 0.487(12) 1 d A 2 . C5A C 0.8691(12) 0.4291(10) 0.4293(8) 0.031(3) Uiso 0.487(12) 1 d A 2 . C21A C 0.8308(13) 0.5420(11) 0.4380(9) 0.034(3) Uiso 0.487(12) 1 d A 2 . H21C H 0.8026 0.5805 0.4999 0.041 Uiso 0.487(12) 1 calc A 2 R H21D H 0.9095 0.5821 0.4294 0.041 Uiso 0.487(12) 1 calc A 2 R O3B O 0.6861(16) 0.5313(10) 0.3683(10) 0.039(3) Uani 0.513(12) 1 d A 1 . C22A C 0.6664(16) 0.6374(11) 0.3738(9) 0.033(4) Uiso 0.487(12) 1 d A 2 . C27A C 0.6936(12) 0.7330(7) 0.4457(8) 0.029(3) Uiso 0.487(12) 1 d A 2 . H27A H 0.7448 0.7330 0.4991 0.035 Uiso 0.487(12) 1 calc A 2 R C26A C 0.6488(9) 0.8304(7) 0.4434(8) 0.030(2) Uiso 0.487(12) 1 d A 2 . H26A H 0.6706 0.8943 0.4946 0.036 Uiso 0.487(12) 1 calc A 2 R C25A C 0.5735(9) 0.8342(7) 0.3675(7) 0.029(2) Uiso 0.487(12) 1 d A 2 . C24A C 0.5380(11) 0.7384(9) 0.2944(8) 0.038(3) Uiso 0.487(12) 1 d A 2 . H24A H 0.4856 0.7395 0.2418 0.046 Uiso 0.487(12) 1 calc A 2 R C23A C 0.5796(15) 0.6400(11) 0.2982(10) 0.045(4) Uiso 0.487(12) 1 d A 2 . H23A H 0.5495 0.5751 0.2502 0.054 Uiso 0.487(12) 1 calc A 2 R I3A I 0.5063(7) 0.9740(4) 0.3548(4) 0.0745(8) Uani 0.487(12) 1 d A 2 . C14A C 0.855(2) 0.2460(19) 0.5710(18) 0.057(7) Uiso 0.487(12) 1 d A 2 . H14C H 0.7679 0.2709 0.5940 0.068 Uiso 0.487(12) 1 calc A 2 R H14D H 0.8507 0.1669 0.5477 0.068 Uiso 0.487(12) 1 calc A 2 R O2B O 0.926(2) 0.275(2) 0.6249(16) 0.044(4) Uani 0.513(12) 1 d A 1 . 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 I2 0.0762(3) 0.0795(3) 0.04318(19) 0.03533(17) 0.01399(16) 0.0148(2) I1 0.0465(2) 0.0842(3) 0.0487(2) 0.01771(17) 0.00843(15) 0.00834(17) I3B 0.0484(8) 0.089(2) 0.187(4) 0.109(2) -0.008(2) 0.0048(15) O2A 0.046(9) 0.041(6) 0.021(6) 0.017(5) -0.011(6) -0.010(7) C9 0.039(2) 0.040(2) 0.036(2) 0.0099(17) -0.0048(18) 0.0009(19) C8 0.043(2) 0.0332(19) 0.035(2) 0.0138(16) -0.0023(18) -0.0035(18) C15 0.058(3) 0.038(2) 0.040(2) 0.0205(18) 0.016(2) 0.006(2) C19 0.044(3) 0.061(3) 0.056(3) 0.038(2) 0.011(2) 0.000(2) C18 0.053(3) 0.043(2) 0.045(2) 0.0227(19) 0.016(2) 0.011(2) C10 0.051(3) 0.052(3) 0.030(2) 0.0097(19) -0.0043(19) 0.004(2) C12 0.042(3) 0.051(3) 0.047(3) 0.019(2) -0.002(2) -0.005(2) C13 0.048(3) 0.043(2) 0.042(2) 0.0066(19) -0.004(2) -0.006(2) C20 0.049(3) 0.061(3) 0.052(3) 0.035(2) 0.007(2) 0.008(2) C11 0.040(2) 0.047(2) 0.039(2) 0.0179(19) 0.0022(18) -0.0021(19) C16 0.058(3) 0.047(2) 0.051(3) 0.021(2) 0.012(2) -0.008(2) O1 0.0409(17) 0.0403(15) 0.0424(16) 0.0054(13) -0.0024(13) -0.0015(14) C2 0.053(3) 0.0295(19) 0.038(2) 0.0135(17) -0.0010(19) 0.0072(19) C1 0.043(2) 0.033(2) 0.034(2) 0.0088(16) 0.0027(18) 0.0032(18) C28 0.044(3) 0.032(2) 0.056(3) 0.0194(19) -0.002(2) 0.0063(19) C21B 0.038(7) 0.026(4) 0.038(5) 0.018(3) -0.001(5) 0.000(4) C7 0.045(3) 0.033(2) 0.039(2) 0.0085(17) -0.0057(19) 0.0003(18) C32 0.049(3) 0.047(2) 0.048(3) 0.028(2) 0.005(2) 0.004(2) C6 0.050(3) 0.035(2) 0.034(2) 0.0167(17) -0.0024(18) 0.0036(19) C33 0.064(3) 0.076(3) 0.034(2) 0.024(2) 0.007(2) 0.013(3) C3B 0.011(6) 0.022(5) 0.044(6) 0.010(4) 0.000(5) -0.002(5) C29 0.062(3) 0.033(2) 0.070(3) 0.017(2) 0.001(3) 0.005(2) C5B 0.021(5) 0.026(4) 0.037(5) 0.016(3) -0.001(4) 0.003(4) C14B 0.047(8) 0.024(5) 0.022(5) 0.016(3) -0.004(6) 0.001(5) C4A 0.036(6) 0.031(5) 0.032(5) 0.010(4) 0.005(5) 0.003(5) C30A 0.046(6) 0.034(4) 0.044(6) 0.014(4) 0.011(5) 0.007(4) C30B 0.032(7) 0.033(5) 0.047(6) 0.015(4) 0.006(5) 0.007(5) C31B 0.052(6) 0.038(5) 0.047(6) 0.008(4) 0.014(5) 0.002(4) C17 0.051(3) 0.061(3) 0.041(2) 0.018(2) 0.004(2) -0.004(2) C4B 0.028(5) 0.031(5) 0.035(5) 0.017(4) -0.006(4) 0.002(4) C31A 0.044(10) 0.067(11) 0.096(12) 0.031(9) 0.021(8) 0.013(7) C3A 0.016(6) 0.037(6) 0.036(5) 0.020(4) -0.009(6) -0.013(6) O3B 0.039(7) 0.026(4) 0.056(6) 0.022(3) 0.001(5) 0.002(4) I3A 0.0604(15) 0.0583(8) 0.1199(15) 0.0541(10) -0.0124(9) 0.0104(7) O2B 0.048(9) 0.052(7) 0.037(10) 0.028(7) -0.020(5) -0.019(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 I2 C18 2.101(4) . ? I1 C11 2.110(5) . ? I3B C25B 2.132(10) . ? O2A C15 1.31(3) . ? O2A C14A 1.40(2) . ? C9 H9 0.9400 . ? C9 C8 1.390(6) . ? C9 C10 1.367(6) . ? O3A C21A 1.48(2) . ? O3A C22A 1.43(2) . ? C8 C13 1.386(6) . ? C8 O1 1.376(5) . ? C15 C20 1.388(7) . ? C15 C16 1.386(7) . ? C15 O2B 1.46(3) . ? C19 H19 0.9400 . ? C19 C18 1.376(7) . ? C19 C20 1.388(6) . ? C18 C17 1.387(7) . ? C10 H10 0.9400 . ? C10 C11 1.371(6) . ? C12 H12 0.9400 . ? C12 C13 1.358(7) . ? C12 C11 1.378(6) . ? C13 H13 0.9400 . ? C20 H20 0.9400 . ? C22B C27B 1.357(12) . ? C22B C23B 1.350(12) . ? C22B O3B 1.33(2) . ? C27B H27B 0.9400 . ? C27B C26B 1.373(11) . ? C23B H23B 0.9400 . ? C23B C24B 1.342(11) . ? C16 H16 0.9400 . ? C16 C17 1.378(6) . ? C25B C26B 1.372(10) . ? C25B C24B 1.354(11) . ? C26B H26B 0.9400 . ? O1 C7 1.438(5) . ? C2 C1 1.403(6) . ? C2 C28 1.528(5) . ? C2 C3B 1.480(15) . ? C2 C3A 1.315(18) . ? C1 C7 1.499(6) . ? C1 C6 1.412(5) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 C29 1.525(6) . ? C21B H21A 0.9800 . ? C21B H21B 0.9800 . ? C21B C5B 1.516(12) . ? C21B O3B 1.410(17) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 C6 1.523(6) . ? C32 C33 1.511(7) . ? C6 C5B 1.485(11) . ? C6 C5A 1.309(13) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C3B C14B 1.48(2) . ? C3B C4B 1.415(17) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C5B C4B 1.385(14) . ? C14B H14A 0.9800 . ? C14B H14B 0.9800 . ? C14B O2B 1.362(19) . ? C4A C30A 1.528(14) . ? C4A C3A 1.41(2) . ? C4A C5A 1.417(16) . ? C30A H30A 0.9800 . ? C30A H30B 0.9800 . ? C30A C31A 1.503(19) . ? C30B H30C 0.9800 . ? C30B H30D 0.9800 . ? C30B C31B 1.511(16) . ? C30B C4B 1.522(17) . ? C31B H31A 0.9700 . ? C31B H31B 0.9700 . ? C31B H31C 0.9700 . ? C17 H17 0.9400 . ? C24B H24B 0.9400 . ? C31A H31D 0.9700 . ? C31A H31E 0.9700 . ? C31A H31F 0.9700 . ? C3A C14A 1.54(3) . ? C5A C21A 1.518(18) . ? C21A H21C 0.9800 . ? C21A H21D 0.9800 . ? C22A C27A 1.364(12) . ? C22A C23A 1.415(12) . ? C27A H27A 0.9400 . ? C27A C26A 1.390(10) . ? C26A H26A 0.9400 . ? C26A C25A 1.366(10) . ? C25A C24A 1.385(11) . ? C25A I3A 2.059(10) . ? C24A H24A 0.9400 . ? C24A C23A 1.402(11) . ? C23A H23A 0.9400 . ? C14A H14C 0.9800 . ? C14A H14D 0.9800 . ? 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 C15 O2A C14A 112(2) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C10 C9 C8 119.9(4) . . ? C22A O3A C21A 114.7(14) . . ? C13 C8 C9 118.6(4) . . ? O1 C8 C9 125.0(4) . . ? O1 C8 C13 116.4(4) . . ? O2A C15 C20 131.8(9) . . ? O2A C15 C16 107.9(9) . . ? O2A C15 O2B 15.5(14) . . ? C20 C15 O2B 116.4(9) . . ? C16 C15 C20 120.3(4) . . ? C16 C15 O2B 123.3(9) . . ? C18 C19 H19 120.3 . . ? C18 C19 C20 119.5(4) . . ? C20 C19 H19 120.3 . . ? C19 C18 I2 118.8(3) . . ? C19 C18 C17 120.9(4) . . ? C17 C18 I2 120.3(4) . . ? C9 C10 H10 119.8 . . ? C9 C10 C11 120.5(4) . . ? C11 C10 H10 119.8 . . ? C13 C12 H12 120.3 . . ? C13 C12 C11 119.3(4) . . ? C11 C12 H12 120.3 . . ? C8 C13 H13 119.3 . . ? C12 C13 C8 121.4(4) . . ? C12 C13 H13 119.3 . . ? C15 C20 H20 120.1 . . ? C19 C20 C15 119.8(4) . . ? C19 C20 H20 120.1 . . ? C23B C22B C27B 120.0(13) . . ? O3B C22B C27B 124.5(12) . . ? O3B C22B C23B 115.5(12) . . ? C22B C27B H27B 120.2 . . ? C22B C27B C26B 119.5(12) . . ? C26B C27B H27B 120.2 . . ? C22B C23B H23B 119.4 . . ? C24B C23B C22B 121.3(13) . . ? C24B C23B H23B 119.4 . . ? C10 C11 I1 119.3(3) . . ? C10 C11 C12 120.3(4) . . ? C12 C11 I1 120.4(3) . . ? C15 C16 H16 120.1 . . ? C17 C16 C15 119.8(4) . . ? C17 C16 H16 120.1 . . ? C26B C25B I3B 115.4(7) . . ? C24B C25B I3B 123.9(7) . . ? C24B C25B C26B 120.6(9) . . ? C27B C26B H26B 120.5 . . ? C25B C26B C27B 119.0(10) . . ? C25B C26B H26B 120.5 . . ? C8 O1 C7 118.9(3) . . ? C1 C2 C28 120.4(4) . . ? C1 C2 C3B 120.1(7) . . ? C3B C2 C28 118.8(7) . . ? C3A C2 C1 119.3(8) . . ? C3A C2 C28 119.1(8) . . ? C3A C2 C3B 19.4(6) . . ? C2 C1 C7 119.4(4) . . ? C2 C1 C6 119.8(4) . . ? C6 C1 C7 120.6(4) . . ? C2 C28 H28A 109.0 . . ? C2 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C29 C28 C2 113.0(4) . . ? C29 C28 H28A 109.0 . . ? C29 C28 H28B 109.0 . . ? H21A C21B H21B 108.2 . . ? C5B C21B H21A 109.7 . . ? C5B C21B H21B 109.7 . . ? O3B C21B H21A 109.7 . . ? O3B C21B H21B 109.7 . . ? O3B C21B C5B 109.6(9) . . ? O1 C7 C1 105.6(3) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.8 . . ? C6 C32 H32A 109.0 . . ? C6 C32 H32B 109.0 . . ? C33 C32 H32A 109.0 . . ? C33 C32 H32B 109.0 . . ? C33 C32 C6 113.0(4) . . ? C1 C6 C32 120.1(4) . . ? C1 C6 C5B 118.1(5) . . ? C5B C6 C32 121.0(4) . . ? C5A C6 C1 120.0(6) . . ? C5A C6 C32 118.8(6) . . ? C5A C6 C5B 19.0(5) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C14B C3B C2 118.9(10) . . ? C4B C3B C2 119.5(12) . . ? C4B C3B C14B 119.9(12) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 118.8(8) . . ? C4B C5B C21B 118.4(9) . . ? C4B C5B C6 122.1(7) . . ? C3B C14B H14A 110.0 . . ? C3B C14B H14B 110.0 . . ? H14A C14B H14B 108.4 . . ? O2B C14B C3B 108.3(19) . . ? O2B C14B H14A 110.0 . . ? O2B C14B H14B 110.0 . . ? C3A C4A C30A 120.1(11) . . ? C3A C4A C5A 118.9(11) . . ? C5A C4A C30A 121.0(9) . . ? C4A C30A H30A 109.7 . . ? C4A C30A H30B 109.7 . . ? H30A C30A H30B 108.2 . . ? C31A C30A C4A 109.8(11) . . ? C31A C30A H30A 109.7 . . ? C31A C30A H30B 109.7 . . ? H30C C30B H30D 107.4 . . ? C31B C30B H30C 108.3 . . ? C31B C30B H30D 108.3 . . ? C31B C30B C4B 115.9(10) . . ? C4B C30B H30C 108.3 . . ? C4B C30B H30D 108.3 . . ? C18 C17 H17 120.1 . . ? C16 C17 C18 119.7(5) . . ? C16 C17 H17 120.1 . . ? C3B C4B C30B 120.1(10) . . ? C5B C4B C3B 119.0(10) . . ? C5B C4B C30B 120.8(8) . . ? C23B C24B C25B 119.3(11) . . ? C23B C24B H24B 120.4 . . ? C25B C24B H24B 120.4 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 120.9(13) . . ? C2 C3A C14A 121.2(15) . . ? C4A C3A C14A 117.8(15) . . ? C6 C5A C4A 119.8(10) . . ? C6 C5A C21A 120.3(10) . . ? C4A C5A C21A 119.8(10) . . ? O3A C21A C5A 109.8(12) . . ? O3A C21A H21C 109.7 . . ? O3A C21A H21D 109.7 . . ? C5A C21A H21C 109.7 . . ? C5A C21A H21D 109.7 . . ? H21C C21A H21D 108.2 . . ? C22B O3B C21B 117.5(12) . . ? C27A C22A O3A 126.1(12) . . ? C27A C22A C23A 116.5(12) . . ? C23A C22A O3A 117.4(12) . . ? C22A C27A H27A 118.6 . . ? C22A C27A C26A 122.7(11) . . ? C26A C27A H27A 118.6 . . ? C27A C26A H26A 119.6 . . ? C25A C26A C27A 120.7(9) . . ? C25A C26A H26A 119.6 . . ? C26A C25A C24A 118.6(8) . . ? C26A C25A I3A 124.2(7) . . ? C24A C25A I3A 117.3(6) . . ? C25A C24A H24A 119.8 . . ? C25A C24A C23A 120.5(9) . . ? C23A C24A H24A 119.8 . . ? C22A C23A H23A 119.7 . . ? C24A C23A C22A 120.6(12) . . ? C24A C23A H23A 119.7 . . ? O2A C14A C3A 108(2) . . ? O2A C14A H14C 110.1 . . ? O2A C14A H14D 110.1 . . ? C3A C14A H14C 110.1 . . ? C3A C14A H14D 110.1 . . ? H14C C14A H14D 108.4 . . ? C14B O2B C15 124(2) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 C18 C17 C16 179.2(3) . . . . ? I3B C25B C26B C27B 179.3(9) . . . . ? I3B C25B C24B C23B 177.0(10) . . . . ? O2A C15 C20 C19 -179.3(15) . . . . ? O2A C15 C16 C17 -179.9(12) . . . . ? O2A C15 O2B C14B 177(10) . . . . ? C9 C8 C13 C12 -0.6(7) . . . . ? C9 C8 O1 C7 0.1(6) . . . . ? C9 C10 C11 I1 176.8(3) . . . . ? C9 C10 C11 C12 -0.6(7) . . . . ? O3A C22A C27A C26A 174.1(15) . . . . ? O3A C22A C23A C24A -172.2(14) . . . . ? C8 C9 C10 C11 -0.3(7) . . . . ? C8 O1 C7 C1 174.5(3) . . . . ? C15 O2A C14A C3A -174.8(15) . . . . ? C15 C16 C17 C18 0.1(7) . . . . ? C19 C18 C17 C16 -1.0(7) . . . . ? C18 C19 C20 C15 -1.6(7) . . . . ? C10 C9 C8 C13 0.8(6) . . . . ? C10 C9 C8 O1 -178.3(4) . . . . ? C13 C8 O1 C7 -179.1(4) . . . . ? C13 C12 C11 I1 -176.6(4) . . . . ? C13 C12 C11 C10 0.8(7) . . . . ? C20 C15 C16 C17 0.1(7) . . . . ? C20 C15 O2B C14B -9(3) . . . . ? C20 C19 C18 I2 -178.4(3) . . . . ? C20 C19 C18 C17 1.7(7) . . . . ? C22B C27B C26B C25B 2(2) . . . . ? C22B C23B C24B C25B 5(2) . . . . ? C27B C22B C23B C24B -7(3) . . . . ? C27B C22B O3B C21B -14(3) . . . . ? C23B C22B C27B C26B 4(2) . . . . ? C23B C22B O3B C21B 168.2(15) . . . . ? C11 C12 C13 C8 -0.2(7) . . . . ? C16 C15 C20 C19 0.7(7) . . . . ? C16 C15 O2B C14B 168.3(17) . . . . ? C26B C25B C24B C23B -0.1(18) . . . . ? O1 C8 C13 C12 178.6(4) . . . . ? C2 C1 C7 O1 -85.6(5) . . . . ? C2 C1 C6 C32 -179.3(4) . . . . ? C2 C1 C6 C5B -9.1(8) . . . . ? C2 C1 C6 C5A 12.5(9) . . . . ? C2 C3B C14B O2B 71.9(18) . . . . ? C2 C3B C4B C5B -0.5(15) . . . . ? C2 C3B C4B C30B 176.8(10) . . . . ? C2 C3A C14A O2A 98(2) . . . . ? C1 C2 C28 C29 -94.2(5) . . . . ? C1 C2 C3B C14B -174.6(10) . . . . ? C1 C2 C3B C4B -9.1(12) . . . . ? C1 C2 C3A C4A 4.2(13) . . . . ? C1 C2 C3A C14A -179.1(12) . . . . ? C1 C6 C5B C21B 169.3(7) . . . . ? C1 C6 C5B C4B -0.5(12) . . . . ? C1 C6 C5A C4A -11.7(13) . . . . ? C1 C6 C5A C21A 171.8(8) . . . . ? C28 C2 C1 C7 0.0(6) . . . . ? C28 C2 C1 C6 -176.2(4) . . . . ? C28 C2 C3B C14B 15.2(13) . . . . ? C28 C2 C3B C4B -179.2(7) . . . . ? C28 C2 C3A C4A 171.9(8) . . . . ? C28 C2 C3A C14A -11.3(15) . . . . ? C21B C5B C4B C3B -164.7(9) . . . . ? C21B C5B C4B C30B 18.0(15) . . . . ? C7 C1 C6 C32 4.6(6) . . . . ? C7 C1 C6 C5B 174.8(6) . . . . ? C7 C1 C6 C5A -163.6(7) . . . . ? C32 C6 C5B C21B -20.6(11) . . . . ? C32 C6 C5B C4B 169.6(8) . . . . ? C32 C6 C5A C4A 180.0(8) . . . . ? C32 C6 C5A C21A 3.5(13) . . . . ? C6 C1 C7 O1 90.5(4) . . . . ? C6 C5B C4B C3B 5.2(15) . . . . ? C6 C5B C4B C30B -172.1(10) . . . . ? C6 C5A C21A O3A 65.0(14) . . . . ? C33 C32 C6 C1 89.4(5) . . . . ? C33 C32 C6 C5B -80.5(7) . . . . ? C33 C32 C6 C5A -102.3(8) . . . . ? C3B C2 C1 C7 -170.0(7) . . . . ? C3B C2 C1 C6 13.8(8) . . . . ? C3B C2 C28 C29 76.0(8) . . . . ? C3B C2 C3A C4A -94(4) . . . . ? C3B C2 C3A C14A 83(4) . . . . ? C3B C14B O2B C15 -175.7(18) . . . . ? C5B C21B O3B C22B -167.1(14) . . . . ? C5B C6 C5A C4A 78(2) . . . . ? C5B C6 C5A C21A -98(2) . . . . ? C14B C3B C4B C5B 164.9(12) . . . . ? C14B C3B C4B C30B -17.8(16) . . . . ? C4A C3A C14A O2A -85(2) . . . . ? C4A C5A C21A O3A -111.5(13) . . . . ? C30A C4A C3A C2 176.2(10) . . . . ? C30A C4A C3A C14A -0.7(18) . . . . ? C30A C4A C5A C6 -172.4(11) . . . . ? C30A C4A C5A C21A 4.1(17) . . . . ? C31B C30B C4B C3B 84.5(13) . . . . ? C31B C30B C4B C5B -98.2(12) . . . . ? C4B C3B C14B O2B -93.6(18) . . . . ? C24B C25B C26B C27B -3.3(17) . . . . ? C3A C2 C1 C7 167.6(7) . . . . ? C3A C2 C1 C6 -8.5(9) . . . . ? C3A C2 C28 C29 98.2(8) . . . . ? C3A C2 C3B C14B -81(4) . . . . ? C3A C2 C3B C4B 84(4) . . . . ? C3A C4A C30A C31A -97.6(13) . . . . ? C3A C4A C5A C6 7.2(16) . . . . ? C3A C4A C5A C21A -176.3(10) . . . . ? C5A C6 C5B C21B 68(2) . . . . ? C5A C6 C5B C4B -101(2) . . . . ? C5A C4A C30A C31A 82.0(14) . . . . ? C5A C4A C3A C2 -3.3(16) . . . . ? C5A C4A C3A C14A 179.8(13) . . . . ? C21A O3A C22A C27A -12(2) . . . . ? C21A O3A C22A C23A 167.3(14) . . . . ? O3B C22B C27B C26B -173.8(16) . . . . ? O3B C22B C23B C24B 170.4(15) . . . . ? O3B C21B C5B C6 80.8(12) . . . . ? O3B C21B C5B C4B -108.9(12) . . . . ? C22A O3A C21A C5A 175.2(13) . . . . ? C22A C27A C26A C25A 0.4(19) . . . . ? C27A C22A C23A C24A 7(2) . . . . ? C27A C26A C25A C24A 2.6(15) . . . . ? C27A C26A C25A I3A -178.2(8) . . . . ? C26A C25A C24A C23A -0.5(17) . . . . ? C25A C24A C23A C22A -5(2) . . . . ? C23A C22A C27A C26A -5(2) . . . . ? I3A C25A C24A C23A -179.8(10) . . . . ? C14A O2A C15 C20 -12(3) . . . . ? C14A O2A C15 C16 167.9(18) . . . . ? C14A O2A C15 O2B -5(6) . . . . ? O2B C15 C20 C19 178.5(13) . . . . ? O2B C15 C16 C17 -177.5(14) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.000 421 36 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962438' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-ea-262K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-ea, 262 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 I3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 I3 O5' _chemical_formula_weight 946.40 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.9501(4) _cell_length_b 13.3296(5) _cell_length_c 15.5931(7) _cell_angle_alpha 110.937(4) _cell_angle_beta 94.265(4) _cell_angle_gamma 91.077(4) _cell_volume 1923.95(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5251 _cell_measurement_temperature 262(2) _cell_measurement_theta_max 29.1419 _cell_measurement_theta_min 3.9780 _exptl_absorpt_coefficient_mu 2.474 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50983 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 924 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_unetI/netI 0.0408 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 20571 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.21 _diffrn_reflns_theta_min 3.99 _diffrn_ambient_temperature 262(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.854 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0635193000 _diffrn_orient_matrix_UB_12 0.0050425000 _diffrn_orient_matrix_UB_13 0.0186089000 _diffrn_orient_matrix_UB_21 0.0316504000 _diffrn_orient_matrix_UB_22 0.0304325000 _diffrn_orient_matrix_UB_23 0.0442772000 _diffrn_orient_matrix_UB_31 -0.0092542000 _diffrn_orient_matrix_UB_32 0.0479812000 _diffrn_orient_matrix_UB_33 -0.0091273000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_special_details ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5861 _reflns_number_total 8923 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 2.014 _refine_diff_density_min -1.525 _refine_diff_density_rms 0.102 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 406 _refine_ls_number_reflns 8923 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0506 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1398 _refine_ls_wR_factor_ref 0.1523 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Others Sof(O2A)=Sof(O3A)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)= Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)= Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(C24A)=Sof(H24A)= Sof(C23A)=Sof(H23A)=Sof(I3A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1) Sof(I3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C24B)=Sof(H24B)=Sof(O3B)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I2 I 0.99330(4) 0.13373(3) 0.97067(3) 0.07122(15) Uani 1 1 d . . . I1 I 1.70855(4) 0.04404(3) 0.12951(3) 0.07103(15) Uani 1 1 d . . . I3B I 0.5151(6) 0.9560(5) 0.3297(7) 0.1055(16) Uani 0.521(12) 1 d A 1 . O2A O 0.9602(10) 0.2776(7) 0.6335(6) 0.042(2) Uiso 0.479(12) 1 d A 2 . C9 C 1.2951(5) 0.1182(4) 0.1872(3) 0.0465(11) Uani 1 1 d . . . H9 H 1.2105 0.0911 0.1575 0.056 Uiso 1 1 calc . . R O3A O 0.7179(10) 0.5349(7) 0.3649(7) 0.041(3) Uiso 0.479(12) 1 d A 2 . C8 C 1.3058(5) 0.2003(3) 0.2726(3) 0.0423(10) Uani 1 1 d . . . C15 C 0.9455(5) 0.2468(3) 0.7066(3) 0.0483(11) Uani 1 1 d . . . C19 C 0.8561(5) 0.1615(4) 0.8025(4) 0.0548(12) Uani 1 1 d . . . H19 H 0.7850 0.1251 0.8162 0.066 Uiso 1 1 calc A . R C18 C 0.9737(5) 0.1851(4) 0.8580(3) 0.0480(11) Uani 1 1 d A . . C10 C 1.4094(5) 0.0769(4) 0.1466(3) 0.0512(11) Uani 1 1 d . . . H10 H 1.4016 0.0223 0.0890 0.061 Uiso 1 1 calc . . R C12 C 1.5475(5) 0.1983(4) 0.2740(4) 0.0526(12) Uani 1 1 d . . . H12 H 1.6324 0.2262 0.3027 0.063 Uiso 1 1 calc . . R C13 C 1.4331(5) 0.2397(4) 0.3149(4) 0.0541(12) Uani 1 1 d . . . H13 H 1.4413 0.2952 0.3722 0.065 Uiso 1 1 calc . . R C20 C 0.8416(5) 0.1913(4) 0.7257(4) 0.0554(12) Uani 1 1 d A . . H20 H 0.7617 0.1737 0.6874 0.066 Uiso 1 1 calc . . R C22B C 0.6710(15) 0.6263(11) 0.3617(9) 0.043(5) Uiso 0.521(12) 1 d A 1 . C27B C 0.7068(13) 0.7238(8) 0.4291(9) 0.043(4) Uiso 0.521(12) 1 d A 1 . H27B H 0.7595 0.7290 0.4825 0.051 Uiso 0.521(12) 1 calc A 1 R C23B C 0.5957(14) 0.6222(11) 0.2843(10) 0.056(4) Uiso 0.521(12) 1 d A 1 . H23B H 0.5816 0.5559 0.2366 0.067 Uiso 0.521(12) 1 calc A 1 R C11 C 1.5352(5) 0.1151(4) 0.1899(3) 0.0500(11) Uani 1 1 d . . . C16 C 1.0641(5) 0.2732(4) 0.7654(4) 0.0568(13) Uani 1 1 d A . . H16 H 1.1338 0.3129 0.7539 0.068 Uiso 1 1 calc . . R C25B C 0.5771(10) 0.8061(9) 0.3369(8) 0.042(3) Uiso 0.521(12) 1 d A 1 . C26B C 0.6612(10) 0.8146(8) 0.4146(9) 0.048(3) Uiso 0.521(12) 1 d A 1 . H26B H 0.6875 0.8823 0.4576 0.057 Uiso 0.521(12) 1 calc A 1 R O1 O 1.1990(3) 0.2475(2) 0.3205(2) 0.0505(8) Uani 1 1 d A . . C2 C 0.9446(5) 0.2263(3) 0.4210(3) 0.0421(10) Uani 1 1 d . . . C1 C 0.9732(5) 0.2674(3) 0.3524(3) 0.0426(10) Uani 1 1 d A . . C28 C 1.0059(5) 0.1224(3) 0.4221(4) 0.0495(11) Uani 1 1 d A . . H28A H 1.0249 0.1276 0.4855 0.059 Uiso 1 1 calc . . R H28B H 1.0908 0.1143 0.3940 0.059 Uiso 1 1 calc . . R C21B C 0.7838(15) 0.5310(8) 0.4395(8) 0.040(3) Uani 0.521(12) 1 d A 1 . H21A H 0.7497 0.5623 0.4996 0.049 Uiso 0.521(12) 1 calc A 1 R H21B H 0.8633 0.5737 0.4384 0.049 Uiso 0.521(12) 1 calc A 1 R C7 C 1.0646(5) 0.2088(4) 0.2799(3) 0.0472(11) Uani 1 1 d . . . H7A H 1.0537 0.1317 0.2645 0.057 Uiso 1 1 calc A . R H7B H 1.0451 0.2248 0.2244 0.057 Uiso 1 1 calc . . R C32 C 0.9508(5) 0.4112(4) 0.2809(3) 0.0524(12) Uani 1 1 d A . . H32A H 0.9525 0.4891 0.3072 0.063 Uiso 1 1 calc . . R H32B H 1.0393 0.3905 0.2603 0.063 Uiso 1 1 calc . . R C6 C 0.9226(5) 0.3660(3) 0.3554(3) 0.0425(10) Uani 1 1 d . . . C33 C 0.8465(6) 0.3720(5) 0.1983(4) 0.0671(15) Uani 1 1 d . . . H33A H 0.8672 0.4044 0.1546 0.101 Uiso 1 1 calc A . GR H33B H 0.7585 0.3916 0.2183 0.101 Uiso 1 1 calc . . GR H33C H 0.8477 0.2952 0.1699 0.101 Uiso 1 1 calc . . GR C3B C 0.8390(12) 0.2736(8) 0.4849(8) 0.039(3) Uani 0.521(12) 1 d A 1 . C29 C 0.9132(6) 0.0228(4) 0.3706(5) 0.0681(16) Uani 1 1 d . . . H29A H 0.9007 0.0135 0.3066 0.102 Uiso 1 1 calc A . GR H29B H 0.8274 0.0318 0.3962 0.102 Uiso 1 1 calc . . GR H29C H 0.9534 -0.0394 0.3769 0.102 Uiso 1 1 calc . . GR C5B C 0.8217(13) 0.4157(15) 0.4235(14) 0.033(3) Uani 0.521(12) 1 d A 1 . C14B C 0.8167(16) 0.2348(10) 0.5596(9) 0.037(3) Uani 0.521(12) 1 d A 1 . H14A H 0.7292 0.2552 0.5821 0.045 Uiso 0.521(12) 1 calc A 1 R H14B H 0.8188 0.1570 0.5375 0.045 Uiso 0.521(12) 1 calc A 1 R C4A C 0.8428(14) 0.3902(9) 0.5004(8) 0.037(3) Uani 0.479(12) 1 d A 2 . C30A C 0.7649(10) 0.4547(8) 0.5797(7) 0.040(3) Uani 0.479(12) 1 d A 2 . H30A H 0.7943 0.5300 0.5994 0.048 Uiso 0.479(12) 1 calc A 2 R H30B H 0.7849 0.4311 0.6311 0.048 Uiso 0.479(12) 1 calc A 2 R C30B C 0.6623(12) 0.4130(9) 0.5417(8) 0.043(3) Uani 0.521(12) 1 d A 1 . H30C H 0.6069 0.4531 0.5127 0.051 Uiso 0.521(12) 1 calc A 1 R H30D H 0.6067 0.3531 0.5430 0.051 Uiso 0.521(12) 1 calc A 1 R C31B C 0.7063(11) 0.4855(8) 0.6401(8) 0.059(3) Uani 0.521(12) 1 d A 1 . H31A H 0.7626 0.5445 0.6396 0.089 Uiso 0.521(12) 1 calc A 1 GR H31B H 0.7560 0.4452 0.6708 0.089 Uiso 0.521(12) 1 calc A 1 GR H31C H 0.6282 0.5125 0.6720 0.089 Uiso 0.521(12) 1 calc A 1 GR C17 C 1.0791(5) 0.2414(4) 0.8396(4) 0.0562(12) Uani 1 1 d . . . H17 H 1.1594 0.2574 0.8774 0.067 Uiso 1 1 calc A . R C4B C 0.7803(12) 0.3682(9) 0.4819(8) 0.038(2) Uani 0.521(12) 1 d A 1 . C24B C 0.5398(13) 0.7080(9) 0.2722(9) 0.057(4) Uiso 0.521(12) 1 d A 1 . H24B H 0.4787 0.7005 0.2220 0.068 Uiso 0.521(12) 1 calc A 1 R C31A C 0.6128(16) 0.4434(14) 0.5544(12) 0.068(4) Uani 0.479(12) 1 d A 2 . H31D H 0.5907 0.4781 0.5111 0.102 Uiso 0.479(12) 1 calc A 2 GR H31E H 0.5670 0.4765 0.6089 0.102 Uiso 0.479(12) 1 calc A 2 GR H31F H 0.5849 0.3686 0.5272 0.102 Uiso 0.479(12) 1 calc A 2 GR C3A C 0.8842(12) 0.2870(10) 0.4915(9) 0.031(3) Uiso 0.479(12) 1 d A 2 . C5A C 0.8695(14) 0.4299(16) 0.4292(15) 0.030(3) Uani 0.479(12) 1 d A 2 . C21A C 0.8295(12) 0.5424(12) 0.4376(10) 0.034(3) Uiso 0.479(12) 1 d A 2 . H21C H 0.7996 0.5796 0.4982 0.041 Uiso 0.479(12) 1 calc A 2 R H21D H 0.9068 0.5830 0.4301 0.041 Uiso 0.479(12) 1 calc A 2 R O3B O 0.6869(10) 0.5328(7) 0.3723(6) 0.045(3) Uiso 0.521(12) 1 d A 1 . C22A C 0.6596(16) 0.6367(11) 0.3742(9) 0.038(5) Uiso 0.479(12) 1 d A 2 . C27A C 0.6891(13) 0.7318(8) 0.4466(9) 0.039(4) Uiso 0.479(12) 1 d A 2 . H27A H 0.7393 0.7309 0.4990 0.047 Uiso 0.479(12) 1 calc A 2 R C26A C 0.6468(10) 0.8284(8) 0.4442(8) 0.035(2) Uiso 0.479(12) 1 d A 2 . H26A H 0.6681 0.8914 0.4946 0.042 Uiso 0.479(12) 1 calc A 2 R C25A C 0.5732(9) 0.8321(8) 0.3674(7) 0.032(2) Uiso 0.479(12) 1 d A 2 . C24A C 0.5393(11) 0.7375(9) 0.2941(9) 0.040(3) Uiso 0.479(12) 1 d A 2 . H24A H 0.4914 0.7395 0.2412 0.047 Uiso 0.479(12) 1 calc A 2 R C23A C 0.5763(15) 0.6389(11) 0.2987(10) 0.049(4) Uiso 0.479(12) 1 d A 2 . H23A H 0.5458 0.5750 0.2518 0.059 Uiso 0.479(12) 1 calc A 2 R I3A I 0.5061(7) 0.9724(4) 0.3551(5) 0.0831(10) Uani 0.479(12) 1 d A 2 . C14A C 0.8577(16) 0.2437(16) 0.5698(15) 0.049(5) Uiso 0.479(12) 1 d A 2 . H14C H 0.7743 0.2702 0.5962 0.059 Uiso 0.479(12) 1 calc A 2 R H14D H 0.8501 0.1657 0.5454 0.059 Uiso 0.479(12) 1 calc A 2 R O2B O 0.9231(11) 0.2826(7) 0.6333(7) 0.055(3) Uiso 0.521(12) 1 d A 1 . 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 I2 0.0888(3) 0.0905(3) 0.0483(2) 0.0397(2) 0.01453(19) 0.0153(2) I1 0.0539(2) 0.0984(3) 0.0548(2) 0.0189(2) 0.01046(17) 0.01019(19) I3B 0.0569(9) 0.103(3) 0.208(5) 0.123(3) -0.013(2) 0.0026(18) C9 0.045(3) 0.050(3) 0.038(2) 0.011(2) -0.007(2) 0.001(2) C8 0.049(3) 0.036(2) 0.040(2) 0.012(2) 0.000(2) -0.0025(19) C15 0.068(3) 0.044(2) 0.043(3) 0.025(2) 0.018(2) 0.012(2) C19 0.051(3) 0.068(3) 0.063(3) 0.043(3) 0.013(2) 0.005(2) C18 0.055(3) 0.050(3) 0.047(3) 0.024(2) 0.017(2) 0.014(2) C10 0.057(3) 0.056(3) 0.032(2) 0.008(2) -0.004(2) 0.002(2) C12 0.047(3) 0.054(3) 0.051(3) 0.013(2) -0.004(2) -0.009(2) C13 0.055(3) 0.048(3) 0.049(3) 0.007(2) -0.004(2) -0.002(2) C20 0.048(3) 0.066(3) 0.067(3) 0.041(3) 0.006(2) 0.003(2) C11 0.047(3) 0.058(3) 0.046(3) 0.020(2) 0.003(2) 0.000(2) C16 0.063(3) 0.054(3) 0.059(3) 0.026(3) 0.013(3) -0.009(2) O1 0.0470(18) 0.0472(18) 0.0446(19) 0.0025(15) -0.0015(15) -0.0021(14) C2 0.051(3) 0.033(2) 0.042(2) 0.0141(19) -0.006(2) 0.0063(19) C1 0.050(3) 0.039(2) 0.038(2) 0.0134(19) 0.000(2) 0.0051(19) C28 0.053(3) 0.038(2) 0.059(3) 0.021(2) -0.002(2) 0.010(2) C21B 0.049(7) 0.028(5) 0.048(6) 0.020(4) 0.000(6) 0.000(5) C7 0.051(3) 0.044(2) 0.043(3) 0.012(2) -0.002(2) 0.004(2) C32 0.062(3) 0.055(3) 0.051(3) 0.031(2) 0.006(2) 0.003(2) C6 0.056(3) 0.035(2) 0.038(2) 0.0151(19) -0.001(2) 0.004(2) C33 0.072(4) 0.086(4) 0.048(3) 0.030(3) -0.003(3) 0.011(3) C3B 0.025(5) 0.041(5) 0.060(7) 0.028(5) 0.008(5) 0.001(4) C29 0.073(4) 0.040(3) 0.088(4) 0.021(3) 0.000(3) 0.006(3) C5B 0.027(7) 0.028(7) 0.044(6) 0.013(5) -0.004(7) -0.002(6) C14B 0.044(7) 0.032(5) 0.040(6) 0.021(4) -0.008(6) 0.006(5) C4A 0.035(6) 0.032(6) 0.041(6) 0.011(5) -0.002(5) 0.001(5) C30A 0.038(5) 0.044(5) 0.043(6) 0.021(5) 0.005(5) -0.004(4) C30B 0.045(8) 0.035(6) 0.054(6) 0.019(5) 0.013(5) 0.020(5) C31B 0.062(7) 0.052(6) 0.057(7) 0.010(5) 0.014(6) -0.001(5) C17 0.054(3) 0.068(3) 0.049(3) 0.025(3) 0.002(2) -0.004(2) C4B 0.035(6) 0.040(6) 0.041(6) 0.019(5) -0.001(5) 0.004(5) C31A 0.050(9) 0.069(10) 0.090(11) 0.029(9) 0.028(7) 0.028(7) C5A 0.027(8) 0.027(6) 0.042(7) 0.021(5) -0.003(8) -0.010(7) I3A 0.0693(16) 0.0634(9) 0.1336(19) 0.0598(13) -0.0135(11) 0.0131(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 I2 C18 2.099(4) . ? I1 C11 2.103(5) . ? I3B C25B 2.140(11) . ? O2A C15 1.359(9) . ? O2A C14A 1.32(2) . ? C9 H9 0.9300 . ? C9 C8 1.383(6) . ? C9 C10 1.370(7) . ? O3A C21A 1.502(16) . ? O3A C22A 1.449(17) . ? C8 C13 1.385(7) . ? C8 O1 1.375(5) . ? C15 C20 1.371(7) . ? C15 C16 1.396(7) . ? C15 O2B 1.393(10) . ? C19 H19 0.9300 . ? C19 C18 1.362(7) . ? C19 C20 1.390(7) . ? C18 C17 1.384(7) . ? C10 H10 0.9300 . ? C10 C11 1.374(7) . ? C12 H12 0.9300 . ? C12 C13 1.374(7) . ? C12 C11 1.376(7) . ? C13 H13 0.9300 . ? C20 H20 0.9300 . ? C22B C27B 1.368(12) . ? C22B C23B 1.355(12) . ? C22B O3B 1.326(17) . ? C27B H27B 0.9300 . ? C27B C26B 1.387(11) . ? C23B H23B 0.9300 . ? C23B C24B 1.348(12) . ? C16 H16 0.9300 . ? C16 C17 1.366(7) . ? C25B C26B 1.389(11) . ? C25B C24B 1.359(12) . ? C26B H26B 0.9300 . ? O1 C7 1.439(6) . ? C2 C1 1.408(6) . ? C2 C28 1.529(5) . ? C2 C3B 1.492(12) . ? C2 C3A 1.306(13) . ? C1 C7 1.505(7) . ? C1 C6 1.403(6) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C29 1.530(7) . ? C21B H21A 0.9700 . ? C21B H21B 0.9700 . ? C21B C5B 1.53(2) . ? C21B O3B 1.377(15) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C6 1.529(6) . ? C32 C33 1.520(7) . ? C6 C5B 1.50(2) . ? C6 C5A 1.32(2) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C3B C14B 1.462(15) . ? C3B C4B 1.413(14) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C5B C4B 1.36(2) . ? C14B H14A 0.9700 . ? C14B H14B 0.9700 . ? C14B O2B 1.455(18) . ? C4A C30A 1.509(16) . ? C4A C3A 1.404(16) . ? C4A C5A 1.43(2) . ? C30A H30A 0.9700 . ? C30A H30B 0.9700 . ? C30A C31A 1.527(18) . ? C30B H30C 0.9700 . ? C30B H30D 0.9700 . ? C30B C31B 1.518(17) . ? C30B C4B 1.547(17) . ? C31B H31A 0.9600 . ? C31B H31B 0.9600 . ? C31B H31C 0.9600 . ? C17 H17 0.9300 . ? C24B H24B 0.9300 . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? C3A C14A 1.56(2) . ? C5A C21A 1.52(2) . ? C21A H21C 0.9700 . ? C21A H21D 0.9700 . ? C22A C27A 1.371(12) . ? C22A C23A 1.398(12) . ? C27A H27A 0.9300 . ? C27A C26A 1.375(11) . ? C26A H26A 0.9300 . ? C26A C25A 1.372(10) . ? C25A C24A 1.381(12) . ? C25A I3A 2.065(11) . ? C24A H24A 0.9300 . ? C24A C23A 1.397(12) . ? C23A H23A 0.9300 . ? C14A H14C 0.9700 . ? C14A H14D 0.9700 . ? 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 C14A O2A C15 112.7(10) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C10 C9 C8 119.9(4) . . ? C22A O3A C21A 114.1(9) . . ? C9 C8 C13 118.8(4) . . ? O1 C8 C9 125.3(4) . . ? O1 C8 C13 115.9(4) . . ? O2A C15 C20 130.9(6) . . ? O2A C15 C16 109.7(6) . . ? O2A C15 O2B 15.6(5) . . ? C20 C15 C16 119.2(4) . . ? C20 C15 O2B 117.9(6) . . ? O2B C15 C16 122.7(6) . . ? C18 C19 H19 119.7 . . ? C18 C19 C20 120.6(4) . . ? C20 C19 H19 119.7 . . ? C19 C18 I2 119.2(3) . . ? C19 C18 C17 120.2(4) . . ? C17 C18 I2 120.6(4) . . ? C9 C10 H10 119.5 . . ? C9 C10 C11 120.9(4) . . ? C11 C10 H10 119.5 . . ? C13 C12 H12 120.3 . . ? C13 C12 C11 119.3(4) . . ? C11 C12 H12 120.3 . . ? C8 C13 H13 119.4 . . ? C12 C13 C8 121.2(5) . . ? C12 C13 H13 119.4 . . ? C15 C20 C19 119.7(5) . . ? C15 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C23B C22B C27B 119.7(13) . . ? O3B C22B C27B 123.8(11) . . ? O3B C22B C23B 115.6(11) . . ? C22B C27B H27B 121.4 . . ? C22B C27B C26B 117.2(11) . . ? C26B C27B H27B 121.4 . . ? C22B C23B H23B 117.9 . . ? C24B C23B C22B 124.1(14) . . ? C24B C23B H23B 117.9 . . ? C10 C11 I1 120.1(4) . . ? C10 C11 C12 119.8(5) . . ? C12 C11 I1 120.1(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 C15 120.9(4) . . ? C17 C16 H16 119.6 . . ? C26B C25B I3B 115.0(7) . . ? C24B C25B I3B 124.7(7) . . ? C24B C25B C26B 120.4(9) . . ? C27B C26B C25B 121.2(10) . . ? C27B C26B H26B 119.4 . . ? C25B C26B H26B 119.4 . . ? C8 O1 C7 118.2(3) . . ? C1 C2 C28 120.3(4) . . ? C1 C2 C3B 120.6(5) . . ? C3B C2 C28 118.5(5) . . ? C3A C2 C1 118.5(6) . . ? C3A C2 C28 120.2(6) . . ? C3A C2 C3B 17.8(7) . . ? C2 C1 C7 119.9(4) . . ? C6 C1 C2 119.6(4) . . ? C6 C1 C7 120.4(4) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? C2 C28 C29 112.7(4) . . ? H28A C28 H28B 107.8 . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? H21A C21B H21B 108.1 . . ? C5B C21B H21A 109.6 . . ? C5B C21B H21B 109.6 . . ? O3B C21B H21A 109.6 . . ? O3B C21B H21B 109.6 . . ? O3B C21B C5B 110.3(10) . . ? O1 C7 C1 105.1(4) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.8 . . ? C6 C32 H32A 109.0 . . ? C6 C32 H32B 109.0 . . ? C33 C32 H32A 109.0 . . ? C33 C32 H32B 109.0 . . ? C33 C32 C6 112.9(4) . . ? C1 C6 C32 120.5(4) . . ? C1 C6 C5B 118.1(8) . . ? C5B C6 C32 120.6(8) . . ? C5A C6 C1 121.0(9) . . ? C5A C6 C32 117.6(8) . . ? C5A C6 C5B 18.9(9) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C14B C3B C2 119.9(8) . . ? C4B C3B C2 118.2(8) . . ? C4B C3B C14B 120.8(10) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 118.8(12) . . ? C4B C5B C21B 118.6(15) . . ? C4B C5B C6 121.8(14) . . ? C3B C14B H14A 110.1 . . ? C3B C14B H14B 110.1 . . ? H14A C14B H14B 108.4 . . ? O2B C14B C3B 108.1(11) . . ? O2B C14B H14A 110.1 . . ? O2B C14B H14B 110.1 . . ? C3A C4A C30A 121.2(10) . . ? C3A C4A C5A 118.1(13) . . ? C5A C4A C30A 120.7(12) . . ? C4A C30A H30A 109.1 . . ? C4A C30A H30B 109.1 . . ? C4A C30A C31A 112.5(11) . . ? H30A C30A H30B 107.8 . . ? C31A C30A H30A 109.1 . . ? C31A C30A H30B 109.1 . . ? H30C C30B H30D 107.6 . . ? C31B C30B H30C 108.7 . . ? C31B C30B H30D 108.7 . . ? C31B C30B C4B 114.2(11) . . ? C4B C30B H30C 108.7 . . ? C4B C30B H30D 108.7 . . ? C18 C17 H17 120.3 . . ? C16 C17 C18 119.4(5) . . ? C16 C17 H17 120.3 . . ? C3B C4B C30B 118.9(9) . . ? C5B C4B C3B 120.6(12) . . ? C5B C4B C30B 120.4(11) . . ? C23B C24B C25B 116.9(11) . . ? C23B C24B H24B 121.5 . . ? C25B C24B H24B 121.5 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 122.8(10) . . ? C2 C3A C14A 118.7(11) . . ? C4A C3A C14A 118.4(12) . . ? C6 C5A C4A 118.9(15) . . ? C6 C5A C21A 121.4(14) . . ? C4A C5A C21A 119.6(17) . . ? O3A C21A C5A 109.5(12) . . ? O3A C21A H21C 109.8 . . ? O3A C21A H21D 109.8 . . ? C5A C21A H21C 109.8 . . ? C5A C21A H21D 109.8 . . ? H21C C21A H21D 108.2 . . ? C22B O3B C21B 116.8(9) . . ? C27A C22A O3A 125.5(11) . . ? C27A C22A C23A 117.9(13) . . ? C23A C22A O3A 116.3(11) . . ? C22A C27A H27A 118.9 . . ? C22A C27A C26A 122.2(12) . . ? C26A C27A H27A 118.9 . . ? C27A C26A H26A 119.9 . . ? C25A C26A C27A 120.1(10) . . ? C25A C26A H26A 119.9 . . ? C26A C25A C24A 119.2(8) . . ? C26A C25A I3A 123.7(7) . . ? C24A C25A I3A 117.1(7) . . ? C25A C24A H24A 119.7 . . ? C25A C24A C23A 120.5(10) . . ? C23A C24A H24A 119.7 . . ? C22A C23A H23A 120.2 . . ? C24A C23A C22A 119.7(13) . . ? C24A C23A H23A 120.2 . . ? O2A C14A C3A 107.8(12) . . ? O2A C14A H14C 110.1 . . ? O2A C14A H14D 110.1 . . ? C3A C14A H14C 110.1 . . ? C3A C14A H14D 110.1 . . ? H14C C14A H14D 108.5 . . ? C15 O2B C14B 122.2(8) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 C18 C17 C16 179.5(4) . . . . ? I3B C25B C26B C27B 178.6(9) . . . . ? I3B C25B C24B C23B 175.5(10) . . . . ? O2A C15 C20 C19 174.5(7) . . . . ? O2A C15 C16 C17 -173.9(6) . . . . ? O2A C15 O2B C14B 128(3) . . . . ? C9 C8 C13 C12 -0.4(7) . . . . ? C9 C8 O1 C7 0.5(6) . . . . ? C9 C10 C11 I1 176.4(4) . . . . ? C9 C10 C11 C12 -2.1(7) . . . . ? O3A C22A C27A C26A 169.3(13) . . . . ? O3A C22A C23A C24A -166.7(13) . . . . ? C8 C9 C10 C11 0.7(7) . . . . ? C8 O1 C7 C1 174.1(3) . . . . ? C15 O2A C14A C3A 178.3(10) . . . . ? C15 C16 C17 C18 -1.9(8) . . . . ? C19 C18 C17 C16 0.1(8) . . . . ? C18 C19 C20 C15 -1.3(8) . . . . ? C10 C9 C8 C13 0.6(7) . . . . ? C10 C9 C8 O1 -179.4(4) . . . . ? C13 C8 O1 C7 -179.4(4) . . . . ? C13 C12 C11 I1 -176.3(4) . . . . ? C13 C12 C11 C10 2.2(7) . . . . ? C20 C15 C16 C17 2.1(8) . . . . ? C20 C15 O2B C14B -21.2(12) . . . . ? C20 C19 C18 I2 -177.9(4) . . . . ? C20 C19 C18 C17 1.5(8) . . . . ? C22B C27B C26B C25B 3.2(19) . . . . ? C22B C23B C24B C25B 9(2) . . . . ? C27B C22B C23B C24B -7(3) . . . . ? C27B C22B O3B C21B -23(2) . . . . ? C23B C22B C27B C26B 1(2) . . . . ? C23B C22B O3B C21B 167.4(13) . . . . ? C11 C12 C13 C8 -1.0(8) . . . . ? C16 C15 C20 C19 -0.5(8) . . . . ? C16 C15 O2B C14B 164.5(8) . . . . ? C26B C25B C24B C23B -4.5(18) . . . . ? O1 C8 C13 C12 179.5(4) . . . . ? C2 C1 C7 O1 -85.7(5) . . . . ? C2 C1 C6 C32 -179.1(4) . . . . ? C2 C1 C6 C5B -9.4(9) . . . . ? C2 C1 C6 C5A 12.1(10) . . . . ? C2 C3B C14B O2B 77.8(12) . . . . ? C2 C3B C4B C5B -1.4(17) . . . . ? C2 C3B C4B C30B 174.9(10) . . . . ? C2 C3A C14A O2A 93.1(16) . . . . ? C1 C2 C28 C29 -93.5(6) . . . . ? C1 C2 C3B C14B -175.9(9) . . . . ? C1 C2 C3B C4B -7.4(13) . . . . ? C1 C2 C3A C4A 2.0(14) . . . . ? C1 C2 C3A C14A -177.4(9) . . . . ? C1 C6 C5B C21B 169.7(9) . . . . ? C1 C6 C5B C4B 0.7(16) . . . . ? C1 C6 C5A C4A -10.5(15) . . . . ? C1 C6 C5A C21A 172.7(9) . . . . ? C28 C2 C1 C7 0.0(6) . . . . ? C28 C2 C1 C6 -176.3(4) . . . . ? C28 C2 C3B C14B 13.0(13) . . . . ? C28 C2 C3B C4B -178.5(8) . . . . ? C28 C2 C3A C4A 170.7(9) . . . . ? C28 C2 C3A C14A -8.7(14) . . . . ? C21B C5B C4B C3B -164.3(11) . . . . ? C21B C5B C4B C30B 19.4(19) . . . . ? C7 C1 C6 C32 4.6(7) . . . . ? C7 C1 C6 C5B 174.4(8) . . . . ? C7 C1 C6 C5A -164.1(8) . . . . ? C32 C6 C5B C21B -20.6(15) . . . . ? C32 C6 C5B C4B 170.4(10) . . . . ? C32 C6 C5A C4A -179.5(9) . . . . ? C32 C6 C5A C21A 3.7(15) . . . . ? C6 C1 C7 O1 90.5(5) . . . . ? C6 C5B C4B C3B 5(2) . . . . ? C6 C5B C4B C30B -171.6(11) . . . . ? C6 C5A C21A O3A 64.2(14) . . . . ? C33 C32 C6 C1 88.1(6) . . . . ? C33 C32 C6 C5B -81.3(9) . . . . ? C33 C32 C6 C5A -102.7(9) . . . . ? C3B C2 C1 C7 -170.9(7) . . . . ? C3B C2 C1 C6 12.8(8) . . . . ? C3B C2 C28 C29 77.6(8) . . . . ? C3B C2 C3A C4A -100(3) . . . . ? C3B C2 C3A C14A 81(3) . . . . ? C3B C14B O2B C15 -167.7(9) . . . . ? C5B C21B O3B C22B -161.9(13) . . . . ? C5B C6 C5A C4A 76(4) . . . . ? C5B C6 C5A C21A -101(5) . . . . ? C14B C3B C4B C5B 167.0(13) . . . . ? C14B C3B C4B C30B -16.7(17) . . . . ? C4A C3A C14A O2A -86.4(15) . . . . ? C4A C5A C21A O3A -112.6(14) . . . . ? C30A C4A C3A C2 175.8(11) . . . . ? C30A C4A C3A C14A -4.8(17) . . . . ? C30A C4A C5A C6 -171.6(11) . . . . ? C30A C4A C5A C21A 5.3(18) . . . . ? C31B C30B C4B C3B 85.3(13) . . . . ? C31B C30B C4B C5B -98.4(14) . . . . ? C4B C3B C14B O2B -90.4(13) . . . . ? C24B C25B C26B C27B -1.4(17) . . . . ? C3A C2 C1 C7 168.7(7) . . . . ? C3A C2 C1 C6 -7.6(9) . . . . ? C3A C2 C28 C29 98.0(8) . . . . ? C3A C2 C3B C14B -87(3) . . . . ? C3A C2 C3B C4B 81(3) . . . . ? C3A C4A C30A C31A -96.1(13) . . . . ? C3A C4A C5A C6 4.7(17) . . . . ? C3A C4A C5A C21A -178.4(11) . . . . ? C5A C6 C5B C21B 65(4) . . . . ? C5A C6 C5B C4B -104(5) . . . . ? C5A C4A C30A C31A 80.1(14) . . . . ? C5A C4A C3A C2 -0.5(17) . . . . ? C5A C4A C3A C14A 179.0(12) . . . . ? C21A O3A C22A C27A -7(2) . . . . ? C21A O3A C22A C23A 166.9(13) . . . . ? O3B C22B C27B C26B -168.0(13) . . . . ? O3B C22B C23B C24B 162.4(14) . . . . ? O3B C21B C5B C6 82.4(13) . . . . ? O3B C21B C5B C4B -108.2(15) . . . . ? C22A O3A C21A C5A 172.2(12) . . . . ? C22A C27A C26A C25A -0.4(19) . . . . ? C27A C22A C23A C24A 7(2) . . . . ? C27A C26A C25A C24A 1.8(16) . . . . ? C27A C26A C25A I3A -179.2(9) . . . . ? C26A C25A C24A C23A 1.6(17) . . . . ? C25A C24A C23A C22A -6(2) . . . . ? C23A C22A C27A C26A -4(2) . . . . ? I3A C25A C24A C23A -177.5(10) . . . . ? C14A O2A C15 C20 -2.9(15) . . . . ? C14A O2A C15 C16 172.5(11) . . . . ? C14A O2A C15 O2B -40(2) . . . . ? O2B C15 C20 C19 -175.0(6) . . . . ? O2B C15 C16 C17 176.3(6) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.006 0.000 0.500 435 39 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962439' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-ea-298K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-ea, 298 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 I3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 I3 O5' _chemical_formula_weight 946.40 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.9945(5) _cell_length_b 13.3552(7) _cell_length_c 15.6205(8) _cell_angle_alpha 110.795(5) _cell_angle_beta 94.271(4) _cell_angle_gamma 90.921(4) _cell_volume 1941.73(17) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4749 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.0822 _cell_measurement_theta_min 3.9187 _exptl_absorpt_coefficient_mu 2.452 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.51960 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 924 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0528 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 20906 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 3.93 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.854 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0633120000 _diffrn_orient_matrix_UB_12 0.0051260000 _diffrn_orient_matrix_UB_13 0.0184929000 _diffrn_orient_matrix_UB_21 0.0314065000 _diffrn_orient_matrix_UB_22 0.0299510000 _diffrn_orient_matrix_UB_23 0.0442188000 _diffrn_orient_matrix_UB_31 -0.0089727000 _diffrn_orient_matrix_UB_32 0.0480721000 _diffrn_orient_matrix_UB_33 -0.0089167000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5403 _reflns_number_total 8949 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.915 _refine_diff_density_min -1.449 _refine_diff_density_rms 0.102 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 426 _refine_ls_number_reflns 8949 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0618 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+0.2441P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1671 _refine_ls_wR_factor_ref 0.1923 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 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 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 3. Others Sof(O2A)=Sof(O3A)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31D)= Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)= Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(C24A)=Sof(H24A)= Sof(C23A)=Sof(H23A)=Sof(I3A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1) Sof(I3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)=Sof(C25B)= Sof(C26B)=Sof(H26B)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C3B)=Sof(C5B)=Sof(C14B)= Sof(H14A)=Sof(H14B)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)= Sof(H31B)=Sof(H31C)=Sof(C4B)=Sof(C24B)=Sof(H24B)=Sof(O3B)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21B(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C21A(H21C,H21D), C14A(H14C,H14D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I2 I 0.99207(5) 0.13200(4) 0.96893(3) 0.0842(2) Uani 1 1 d . . . I1 I 1.70680(5) 0.04615(4) 0.12983(3) 0.0859(2) Uani 1 1 d . . . I3B I 0.5147(7) 0.9535(6) 0.3281(8) 0.122(2) Uani 0.526(15) 1 d A 1 . O2A O 0.952(4) 0.267(3) 0.624(2) 0.057(6) Uani 0.474(15) 1 d A 2 . C9 C 1.2957(6) 0.1187(4) 0.1881(4) 0.0553(13) Uani 1 1 d . . . H9 H 1.2115 0.0919 0.1584 0.066 Uiso 1 1 calc . . R O3A O 0.7255(13) 0.5356(11) 0.3650(10) 0.048(4) Uiso 0.474(15) 1 d A 2 . C8 C 1.3057(5) 0.2003(4) 0.2724(4) 0.0509(12) Uani 1 1 d . . . C15 C 0.9452(6) 0.2456(4) 0.7068(4) 0.0584(14) Uani 1 1 d . . . C19 C 0.8557(6) 0.1607(5) 0.8007(5) 0.0689(17) Uani 1 1 d . . . H19 H 0.7843 0.1246 0.8138 0.083 Uiso 1 1 calc A . R C18 C 0.9733(6) 0.1837(4) 0.8574(4) 0.0545(13) Uani 1 1 d A . . C10 C 1.4094(6) 0.0764(5) 0.1475(4) 0.0632(15) Uani 1 1 d . . . H10 H 1.4023 0.0205 0.0908 0.076 Uiso 1 1 calc . . R C12 C 1.5453(6) 0.1982(5) 0.2742(4) 0.0621(15) Uani 1 1 d . . . H12 H 1.6300 0.2252 0.3027 0.075 Uiso 1 1 calc . . R C13 C 1.4324(6) 0.2400(5) 0.3158(4) 0.0643(16) Uani 1 1 d . . . H13 H 1.4404 0.2948 0.3731 0.077 Uiso 1 1 calc . . R C20 C 0.8430(7) 0.1906(5) 0.7249(5) 0.0675(16) Uani 1 1 d A . . H20 H 0.7642 0.1730 0.6861 0.081 Uiso 1 1 calc . . R C22B C 0.667(2) 0.6255(13) 0.3627(11) 0.052(6) Uiso 0.526(15) 1 d A 1 . C27B C 0.7085(12) 0.7250(7) 0.4298(9) 0.038(3) Uiso 0.526(15) 1 d A 1 . H27B H 0.7654 0.7304 0.4813 0.046 Uiso 0.526(15) 1 calc A 1 R C23B C 0.5965(16) 0.6220(12) 0.2821(12) 0.063(5) Uiso 0.526(15) 1 d A 1 . H23B H 0.5871 0.5570 0.2329 0.076 Uiso 0.526(15) 1 calc A 1 R C11 C 1.5329(6) 0.1165(5) 0.1905(4) 0.0612(14) Uani 1 1 d . . . C16 C 1.0619(6) 0.2723(5) 0.7637(4) 0.0655(16) Uani 1 1 d A . . H16 H 1.1308 0.3119 0.7518 0.079 Uiso 1 1 calc . . R C25B C 0.5761(12) 0.8055(11) 0.3368(9) 0.054(3) Uiso 0.526(15) 1 d A 1 . C26B C 0.6601(13) 0.8148(10) 0.4152(10) 0.060(4) Uiso 0.526(15) 1 d A 1 . H26B H 0.6840 0.8825 0.4583 0.071 Uiso 0.526(15) 1 calc A 1 R O1 O 1.1989(4) 0.2469(3) 0.3206(3) 0.0599(10) Uani 1 1 d A . . C2 C 0.9450(5) 0.2264(4) 0.4203(4) 0.0488(12) Uani 1 1 d . . . C1 C 0.9732(5) 0.2672(4) 0.3526(3) 0.0486(12) Uani 1 1 d A . . C28 C 1.0056(6) 0.1232(4) 0.4228(5) 0.0628(15) Uani 1 1 d A . . H28A H 1.0210 0.1278 0.4861 0.075 Uiso 1 1 calc . . R H28B H 1.0917 0.1154 0.3968 0.075 Uiso 1 1 calc . . R C21B C 0.785(2) 0.5373(16) 0.4419(17) 0.049(5) Uani 0.526(15) 1 d A 1 . H21A H 0.7504 0.5689 0.5016 0.058 Uiso 0.526(15) 1 calc A 1 R H21B H 0.8625 0.5805 0.4395 0.058 Uiso 0.526(15) 1 calc A 1 R C7 C 1.0655(5) 0.2081(4) 0.2804(4) 0.0539(13) Uani 1 1 d . . . H7A H 1.0552 0.1313 0.2657 0.065 Uiso 1 1 calc A . R H7B H 1.0462 0.2235 0.2246 0.065 Uiso 1 1 calc . . R C32 C 0.9520(7) 0.4104(5) 0.2795(4) 0.0631(15) Uani 1 1 d A . . H32A H 0.9564 0.4882 0.3051 0.076 Uiso 1 1 calc . . R H32B H 1.0389 0.3875 0.2580 0.076 Uiso 1 1 calc . . R C6 C 0.9244(6) 0.3674(4) 0.3556(4) 0.0491(12) Uani 1 1 d . . . C33 C 0.8478(8) 0.3737(6) 0.1995(4) 0.0816(19) Uani 1 1 d . . . H33A H 0.8677 0.4065 0.1560 0.122 Uiso 1 1 calc A . GR H33B H 0.7610 0.3940 0.2205 0.122 Uiso 1 1 calc . . GR H33C H 0.8480 0.2972 0.1706 0.122 Uiso 1 1 calc . . GR C3B C 0.8441(18) 0.2701(10) 0.4806(10) 0.050(4) Uani 0.526(15) 1 d A 1 . C29 C 0.9134(7) 0.0238(5) 0.3688(6) 0.081(2) Uani 1 1 d . . . H29A H 0.9037 0.0157 0.3050 0.122 Uiso 1 1 calc A . GR H29B H 0.8268 0.0325 0.3926 0.122 Uiso 1 1 calc . . GR H29C H 0.9522 -0.0388 0.3750 0.122 Uiso 1 1 calc . . GR C5B C 0.8242(14) 0.4188(14) 0.4249(12) 0.032(3) Uani 0.526(15) 1 d A 1 . C14B C 0.8142(18) 0.2339(13) 0.5573(11) 0.055(4) Uani 0.526(15) 1 d A 1 . H14A H 0.8147 0.1563 0.5375 0.066 Uiso 0.526(15) 1 calc A 1 R H14B H 0.7267 0.2565 0.5778 0.066 Uiso 0.526(15) 1 calc A 1 R C4A C 0.8433(14) 0.3912(12) 0.5028(10) 0.043(3) Uani 0.474(15) 1 d A 2 . C30A C 0.7659(11) 0.4527(9) 0.5779(8) 0.045(3) Uani 0.474(15) 1 d A 2 . H30A H 0.7920 0.5281 0.5960 0.054 Uiso 0.474(15) 1 calc A 2 R H30B H 0.7878 0.4312 0.6303 0.054 Uiso 0.474(15) 1 calc A 2 R C30B C 0.6683(19) 0.4144(14) 0.5406(14) 0.067(5) Uani 0.526(15) 1 d A 1 . H30C H 0.6135 0.4551 0.5119 0.081 Uiso 0.526(15) 1 calc A 1 R H30D H 0.6128 0.3543 0.5408 0.081 Uiso 0.526(15) 1 calc A 1 R C31B C 0.7089(14) 0.4837(10) 0.6372(10) 0.074(4) Uani 0.526(15) 1 d A 1 . H31A H 0.7653 0.5430 0.6380 0.111 Uiso 0.526(15) 1 calc A 1 GR H31B H 0.7574 0.4428 0.6678 0.111 Uiso 0.526(15) 1 calc A 1 GR H31C H 0.6303 0.5103 0.6682 0.111 Uiso 0.526(15) 1 calc A 1 GR C17 C 1.0768(6) 0.2400(5) 0.8389(4) 0.0638(15) Uani 1 1 d . . . H17 H 1.1565 0.2563 0.8768 0.077 Uiso 1 1 calc A . R C4B C 0.7847(15) 0.3709(8) 0.4819(7) 0.036(3) Uani 0.526(15) 1 d A 1 . C24B C 0.5407(14) 0.7092(10) 0.2713(11) 0.061(4) Uiso 0.526(15) 1 d A 1 . H24B H 0.4807 0.7029 0.2210 0.073 Uiso 0.526(15) 1 calc A 1 R C31A C 0.616(2) 0.4380(19) 0.5535(18) 0.081(6) Uani 0.474(15) 1 d A 2 . H31D H 0.5915 0.4709 0.5094 0.121 Uiso 0.474(15) 1 calc A 2 GR H31E H 0.5705 0.4709 0.6078 0.121 Uiso 0.474(15) 1 calc A 2 GR H31F H 0.5911 0.3629 0.5277 0.121 Uiso 0.474(15) 1 calc A 2 GR C3A C 0.8813(17) 0.2898(15) 0.4950(12) 0.045(5) Uiso 0.474(15) 1 d A 2 . C5A C 0.8732(15) 0.4283(17) 0.4271(15) 0.036(4) Uani 0.474(15) 1 d A 2 . C21A C 0.831(2) 0.535(2) 0.4336(17) 0.045(5) Uani 0.474(15) 1 d A 2 . H21C H 0.8000 0.5701 0.4940 0.054 Uiso 0.474(15) 1 calc A 2 R H21D H 0.9084 0.5761 0.4285 0.054 Uiso 0.474(15) 1 calc A 2 R O3B O 0.6868(11) 0.5320(8) 0.3726(8) 0.050(3) Uani 0.526(15) 1 d A 1 . C22A C 0.667(2) 0.6388(15) 0.3748(12) 0.050(6) Uiso 0.474(15) 1 d A 2 . C27A C 0.6867(16) 0.7312(10) 0.4503(12) 0.059(5) Uiso 0.474(15) 1 d A 2 . H27A H 0.7270 0.7291 0.5052 0.071 Uiso 0.474(15) 1 calc A 2 R C26A C 0.6474(12) 0.8270(10) 0.4449(10) 0.049(3) Uiso 0.474(15) 1 d A 2 . H26A H 0.6696 0.8902 0.4945 0.058 Uiso 0.474(15) 1 calc A 2 R C25A C 0.5760(10) 0.8314(9) 0.3677(8) 0.036(3) Uiso 0.474(15) 1 d A 2 . C24A C 0.5371(14) 0.7384(10) 0.2967(10) 0.051(4) Uiso 0.474(15) 1 d A 2 . H24A H 0.4840 0.7401 0.2458 0.061 Uiso 0.474(15) 1 calc A 2 R C23A C 0.5782(16) 0.6395(13) 0.3011(12) 0.060(5) Uiso 0.474(15) 1 d A 2 . H23A H 0.5468 0.5754 0.2554 0.072 Uiso 0.474(15) 1 calc A 2 R I3A I 0.5068(8) 0.9718(5) 0.3555(5) 0.0979(12) Uani 0.474(15) 1 d A 2 . C14A C 0.8550(19) 0.2467(16) 0.5699(14) 0.045(5) Uiso 0.474(15) 1 d A 2 . H14C H 0.7774 0.2793 0.6007 0.054 Uiso 0.474(15) 1 calc A 2 R H14D H 0.8371 0.1697 0.5437 0.054 Uiso 0.474(15) 1 calc A 2 R O2B O 0.931(4) 0.289(2) 0.640(2) 0.055(6) Uani 0.526(15) 1 d A 1 . 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 I2 0.1042(4) 0.1054(4) 0.0580(3) 0.0454(3) 0.0157(3) 0.0153(3) I1 0.0660(3) 0.1175(4) 0.0663(3) 0.0212(3) 0.0142(2) 0.0130(3) I3B 0.0688(12) 0.117(3) 0.237(6) 0.138(4) -0.018(3) 0.001(2) O2A 0.077(10) 0.060(15) 0.055(15) 0.041(13) 0.023(10) 0.019(9) C9 0.059(3) 0.056(3) 0.044(3) 0.011(2) -0.004(3) 0.000(3) C8 0.051(3) 0.051(3) 0.049(3) 0.017(2) 0.002(2) 0.002(2) C15 0.074(4) 0.054(3) 0.062(4) 0.037(3) 0.020(3) 0.013(3) C19 0.060(4) 0.087(4) 0.078(4) 0.049(4) 0.018(3) 0.005(3) C18 0.066(4) 0.056(3) 0.053(3) 0.032(3) 0.016(3) 0.009(3) C10 0.071(4) 0.073(4) 0.039(3) 0.011(3) 0.004(3) 0.006(3) C12 0.058(3) 0.063(3) 0.060(4) 0.017(3) -0.001(3) -0.007(3) C13 0.065(4) 0.058(3) 0.051(3) -0.002(3) -0.004(3) -0.004(3) C20 0.066(4) 0.080(4) 0.076(4) 0.051(3) 0.003(3) 0.004(3) C11 0.058(3) 0.068(4) 0.061(4) 0.027(3) 0.009(3) 0.003(3) C16 0.070(4) 0.071(4) 0.063(4) 0.032(3) 0.012(3) -0.013(3) O1 0.059(2) 0.055(2) 0.053(2) 0.0053(17) -0.0034(18) -0.0036(17) C2 0.059(3) 0.038(2) 0.052(3) 0.019(2) -0.002(3) 0.010(2) C1 0.054(3) 0.046(3) 0.039(3) 0.008(2) -0.001(2) 0.002(2) C28 0.064(4) 0.050(3) 0.079(4) 0.029(3) 0.005(3) 0.019(3) C21B 0.062(14) 0.034(6) 0.061(9) 0.026(6) 0.026(9) 0.028(8) C7 0.056(3) 0.054(3) 0.043(3) 0.009(2) -0.003(2) 0.005(2) C32 0.077(4) 0.060(3) 0.063(4) 0.034(3) 0.011(3) 0.008(3) C6 0.065(3) 0.043(3) 0.041(3) 0.019(2) 0.001(3) 0.009(2) C33 0.090(5) 0.105(5) 0.052(4) 0.032(4) -0.003(3) 0.006(4) C3B 0.071(9) 0.026(6) 0.050(7) 0.014(5) -0.013(7) -0.010(6) C29 0.085(5) 0.049(3) 0.105(6) 0.023(3) -0.005(4) 0.009(3) C5B 0.023(8) 0.038(7) 0.040(6) 0.017(5) 0.012(7) 0.008(6) C14B 0.054(9) 0.058(8) 0.062(9) 0.036(6) -0.009(7) -0.003(7) C4A 0.022(6) 0.059(8) 0.046(8) 0.020(6) -0.011(5) -0.007(5) C30A 0.025(6) 0.053(6) 0.048(7) 0.009(5) 0.003(5) -0.002(5) C30B 0.070(15) 0.060(8) 0.086(10) 0.033(8) 0.045(10) 0.032(8) C31B 0.069(8) 0.064(7) 0.075(10) 0.007(6) 0.012(7) -0.011(6) C17 0.064(4) 0.071(4) 0.056(4) 0.024(3) 0.002(3) -0.010(3) C4B 0.040(7) 0.033(5) 0.030(5) 0.006(4) -0.009(5) 0.011(5) C31A 0.056(13) 0.085(14) 0.103(15) 0.029(12) 0.044(10) 0.020(9) C5A 0.014(8) 0.042(6) 0.061(8) 0.030(5) 0.006(7) -0.003(7) C21A 0.046(11) 0.060(9) 0.030(7) 0.013(6) 0.012(7) 0.027(8) O3B 0.033(5) 0.052(5) 0.076(6) 0.036(4) 0.010(5) 0.007(4) I3A 0.0821(17) 0.0726(11) 0.156(2) 0.0662(17) -0.0169(13) 0.0143(9) O2B 0.082(15) 0.041(8) 0.041(8) 0.012(6) 0.017(8) 0.002(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 I2 C18 2.088(5) . ? I1 C11 2.113(6) . ? I3B C25B 2.126(13) . ? O2A C15 1.43(3) . ? O2A C14A 1.20(5) . ? C9 H9 0.9300 . ? C9 C8 1.374(7) . ? C9 C10 1.374(8) . ? O3A C21A 1.45(3) . ? O3A C22A 1.47(2) . ? C8 C13 1.392(8) . ? C8 O1 1.379(6) . ? C15 C20 1.352(8) . ? C15 C16 1.372(9) . ? C15 O2B 1.36(4) . ? C19 H19 0.9300 . ? C19 C18 1.378(9) . ? C19 C20 1.376(8) . ? C18 C17 1.375(8) . ? C10 H10 0.9300 . ? C10 C11 1.364(9) . ? C12 H12 0.9300 . ? C12 C13 1.371(9) . ? C12 C11 1.369(8) . ? C13 H13 0.9300 . ? C20 H20 0.9300 . ? C22B C27B 1.402(13) . ? C22B C23B 1.380(13) . ? C22B O3B 1.33(2) . ? C27B H27B 0.9300 . ? C27B C26B 1.386(11) . ? C23B H23B 0.9300 . ? C23B C24B 1.357(13) . ? C16 H16 0.9300 . ? C16 C17 1.388(9) . ? C25B C26B 1.399(12) . ? C25B C24B 1.349(12) . ? C26B H26B 0.9300 . ? O1 C7 1.436(6) . ? C2 C1 1.394(7) . ? C2 C28 1.526(7) . ? C2 C3B 1.419(17) . ? C2 C3A 1.382(19) . ? C1 C7 1.515(7) . ? C1 C6 1.417(7) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C29 1.540(9) . ? C21B H21A 0.9700 . ? C21B H21B 0.9700 . ? C21B C5B 1.57(3) . ? C21B O3B 1.39(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C6 1.532(7) . ? C32 C33 1.498(9) . ? C6 C5B 1.517(16) . ? C6 C5A 1.27(2) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C3B C14B 1.49(2) . ? C3B C4B 1.474(16) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C5B C4B 1.34(2) . ? C14B H14A 0.9700 . ? C14B H14B 0.9700 . ? C14B O2B 1.63(4) . ? C4A C30A 1.456(18) . ? C4A C3A 1.38(2) . ? C4A C5A 1.48(2) . ? C30A H30A 0.9700 . ? C30A H30B 0.9700 . ? C30A C31A 1.51(2) . ? C30B H30C 0.9700 . ? C30B H30D 0.9700 . ? C30B C31B 1.48(3) . ? C30B C4B 1.53(2) . ? C31B H31A 0.9600 . ? C31B H31B 0.9600 . ? C31B H31C 0.9600 . ? C17 H17 0.9300 . ? C24B H24B 0.9300 . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? C3A C14A 1.51(3) . ? C5A C21A 1.46(3) . ? C21A H21C 0.9700 . ? C21A H21D 0.9700 . ? C22A C27A 1.371(14) . ? C22A C23A 1.400(13) . ? C27A H27A 0.9300 . ? C27A C26A 1.373(12) . ? C26A H26A 0.9300 . ? C26A C25A 1.375(12) . ? C25A C24A 1.367(13) . ? C25A I3A 2.075(12) . ? C24A H24A 0.9300 . ? C24A C23A 1.412(13) . ? C23A H23A 0.9300 . ? C14A H14C 0.9700 . ? C14A H14D 0.9700 . ? 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 C14A O2A C15 118(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C10 C9 C8 120.3(5) . . ? C21A O3A C22A 117.6(14) . . ? C9 C8 C13 119.3(5) . . ? C9 C8 O1 125.4(5) . . ? O1 C8 C13 115.3(5) . . ? C20 C15 O2A 125.1(19) . . ? C20 C15 C16 120.6(5) . . ? C20 C15 O2B 122.0(17) . . ? C16 C15 O2A 113.7(19) . . ? O2B C15 O2A 16(2) . . ? O2B C15 C16 116.8(17) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C20 C19 C18 120.6(5) . . ? C19 C18 I2 119.7(4) . . ? C17 C18 I2 121.1(5) . . ? C17 C18 C19 119.2(5) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.8(5) . . ? C11 C10 H10 120.1 . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C11 C12 C13 119.8(6) . . ? C8 C13 H13 120.0 . . ? C12 C13 C8 120.0(5) . . ? C12 C13 H13 120.0 . . ? C15 C20 C19 119.9(6) . . ? C15 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C23B C22B C27B 119.6(15) . . ? O3B C22B C27B 123.8(13) . . ? O3B C22B C23B 116.6(12) . . ? C22B C27B H27B 121.9 . . ? C26B C27B C22B 116.3(12) . . ? C26B C27B H27B 121.9 . . ? C22B C23B H23B 118.6 . . ? C24B C23B C22B 122.9(15) . . ? C24B C23B H23B 118.6 . . ? C10 C11 I1 119.3(4) . . ? C10 C11 C12 120.9(6) . . ? C12 C11 I1 119.7(5) . . ? C15 C16 H16 120.1 . . ? C15 C16 C17 119.8(5) . . ? C17 C16 H16 120.1 . . ? C26B C25B I3B 114.9(9) . . ? C24B C25B I3B 123.5(9) . . ? C24B C25B C26B 121.6(11) . . ? C27B C26B C25B 121.2(11) . . ? C27B C26B H26B 119.4 . . ? C25B C26B H26B 119.4 . . ? C8 O1 C7 118.1(4) . . ? C1 C2 C28 121.1(5) . . ? C1 C2 C3B 120.9(7) . . ? C3B C2 C28 117.3(7) . . ? C3A C2 C1 118.9(9) . . ? C3A C2 C28 118.9(9) . . ? C3A C2 C3B 18.3(8) . . ? C2 C1 C7 119.4(5) . . ? C2 C1 C6 120.2(5) . . ? C6 C1 C7 120.2(5) . . ? C2 C28 H28A 109.2 . . ? C2 C28 H28B 109.2 . . ? C2 C28 C29 111.9(5) . . ? H28A C28 H28B 107.9 . . ? C29 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? H21A C21B H21B 108.6 . . ? C5B C21B H21A 110.4 . . ? C5B C21B H21B 110.4 . . ? O3B C21B H21A 110.4 . . ? O3B C21B H21B 110.4 . . ? O3B C21B C5B 106.4(17) . . ? O1 C7 C1 105.3(4) . . ? O1 C7 H7A 110.7 . . ? O1 C7 H7B 110.7 . . ? C1 C7 H7A 110.7 . . ? C1 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 107.7 . . ? C6 C32 H32A 108.9 . . ? C6 C32 H32B 108.9 . . ? C33 C32 H32A 108.9 . . ? C33 C32 H32B 108.9 . . ? C33 C32 C6 113.4(5) . . ? C1 C6 C32 120.1(5) . . ? C1 C6 C5B 117.8(8) . . ? C5B C6 C32 121.2(8) . . ? C5A C6 C1 120.1(10) . . ? C5A C6 C32 119.2(10) . . ? C5A C6 C5B 18.0(9) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 123.5(12) . . ? C2 C3B C4B 119.2(11) . . ? C4B C3B C14B 116.0(13) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 119.6(12) . . ? C4B C5B C21B 118.9(14) . . ? C4B C5B C6 120.7(13) . . ? C3B C14B H14A 110.4 . . ? C3B C14B H14B 110.4 . . ? C3B C14B O2B 106.5(17) . . ? H14A C14B H14B 108.6 . . ? O2B C14B H14A 110.4 . . ? O2B C14B H14B 110.4 . . ? C30A C4A C5A 122.7(14) . . ? C3A C4A C30A 120.2(13) . . ? C3A C4A C5A 116.8(15) . . ? C4A C30A H30A 108.9 . . ? C4A C30A H30B 108.9 . . ? C4A C30A C31A 113.3(14) . . ? H30A C30A H30B 107.7 . . ? C31A C30A H30A 108.9 . . ? C31A C30A H30B 108.9 . . ? H30C C30B H30D 107.5 . . ? C31B C30B H30C 108.6 . . ? C31B C30B H30D 108.6 . . ? C31B C30B C4B 114.8(17) . . ? C4B C30B H30C 108.6 . . ? C4B C30B H30D 108.6 . . ? C18 C17 C16 119.8(6) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C3B C4B C30B 119.9(11) . . ? C5B C4B C3B 119.9(12) . . ? C5B C4B C30B 119.9(11) . . ? C23B C24B H24B 121.4 . . ? C25B C24B C23B 117.1(13) . . ? C25B C24B H24B 121.4 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C14A 118.8(15) . . ? C4A C3A C2 121.3(15) . . ? C4A C3A C14A 119.9(16) . . ? C6 C5A C4A 121.8(17) . . ? C6 C5A C21A 120.7(18) . . ? C21A C5A C4A 117.3(18) . . ? O3A C21A C5A 115(2) . . ? O3A C21A H21C 108.5 . . ? O3A C21A H21D 108.5 . . ? C5A C21A H21C 108.5 . . ? C5A C21A H21D 108.5 . . ? H21C C21A H21D 107.5 . . ? C22B O3B C21B 113.9(12) . . ? C27A C22A O3A 125.7(14) . . ? C27A C22A C23A 118.3(17) . . ? C23A C22A O3A 115.9(13) . . ? C22A C27A H27A 120.0 . . ? C22A C27A C26A 120.1(15) . . ? C26A C27A H27A 120.0 . . ? C27A C26A H26A 119.3 . . ? C27A C26A C25A 121.3(12) . . ? C25A C26A H26A 119.3 . . ? C26A C25A I3A 123.9(8) . . ? C24A C25A C26A 119.5(10) . . ? C24A C25A I3A 116.4(8) . . ? C25A C24A H24A 120.2 . . ? C25A C24A C23A 119.5(12) . . ? C23A C24A H24A 120.2 . . ? C22A C23A C24A 119.5(15) . . ? C22A C23A H23A 120.3 . . ? C24A C23A H23A 120.3 . . ? O2A C14A C3A 108(2) . . ? O2A C14A H14C 110.0 . . ? O2A C14A H14D 110.0 . . ? C3A C14A H14C 110.0 . . ? C3A C14A H14D 110.0 . . ? H14C C14A H14D 108.4 . . ? C15 O2B C14B 116(2) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 C18 C17 C16 179.3(5) . . . . ? I3B C25B C26B C27B -179.7(10) . . . . ? I3B C25B C24B C23B 174.5(11) . . . . ? O2A C15 C20 C19 170.3(15) . . . . ? O2A C15 C16 C17 -169.6(14) . . . . ? O2A C15 O2B C14B 82(12) . . . . ? C9 C8 C13 C12 0.5(9) . . . . ? C9 C8 O1 C7 -0.1(8) . . . . ? C9 C10 C11 I1 177.3(5) . . . . ? C9 C10 C11 C12 0.5(9) . . . . ? O3A C22A C27A C26A 167.6(17) . . . . ? O3A C22A C23A C24A -168.1(16) . . . . ? C8 C9 C10 C11 -0.9(9) . . . . ? C8 O1 C7 C1 175.0(4) . . . . ? C15 O2A C14A C3A 172.7(19) . . . . ? C15 C16 C17 C18 -1.6(9) . . . . ? C19 C18 C17 C16 -0.3(9) . . . . ? C18 C19 C20 C15 -1.8(10) . . . . ? C10 C9 C8 C13 0.4(9) . . . . ? C10 C9 C8 O1 -178.3(5) . . . . ? C13 C8 O1 C7 -178.8(5) . . . . ? C13 C12 C11 I1 -176.5(5) . . . . ? C13 C12 C11 C10 0.3(10) . . . . ? C20 C15 C16 C17 1.8(9) . . . . ? C20 C15 O2B C14B -24(2) . . . . ? C20 C19 C18 I2 -177.6(5) . . . . ? C20 C19 C18 C17 2.0(9) . . . . ? C22B C27B C26B C25B -1(2) . . . . ? C22B C23B C24B C25B 12(2) . . . . ? C27B C22B C23B C24B -14(3) . . . . ? C27B C22B O3B C21B -18(3) . . . . ? C23B C22B C27B C26B 8(3) . . . . ? C23B C22B O3B C21B 164.4(17) . . . . ? C11 C12 C13 C8 -0.8(10) . . . . ? C16 C15 C20 C19 -0.2(10) . . . . ? C16 C15 O2B C14B 164.5(13) . . . . ? C26B C25B C24B C23B -4(2) . . . . ? O1 C8 C13 C12 179.3(6) . . . . ? C2 C1 C7 O1 -86.1(6) . . . . ? C2 C1 C6 C32 -178.2(5) . . . . ? C2 C1 C6 C5B -9.3(10) . . . . ? C2 C1 C6 C5A 11.2(11) . . . . ? C2 C3B C14B O2B 77.6(17) . . . . ? C2 C3B C4B C5B 1.5(19) . . . . ? C2 C3B C4B C30B 175.1(14) . . . . ? C2 C3A C14A O2A 87(2) . . . . ? C1 C2 C28 C29 -91.8(7) . . . . ? C1 C2 C3B C14B -176.7(11) . . . . ? C1 C2 C3B C4B -10.3(15) . . . . ? C1 C2 C3A C4A 1.2(17) . . . . ? C1 C2 C3A C14A -177.9(10) . . . . ? C1 C6 C5B C21B 170.3(14) . . . . ? C1 C6 C5B C4B 0.6(15) . . . . ? C1 C6 C5A C4A -9.6(16) . . . . ? C1 C6 C5A C21A 175.8(14) . . . . ? C28 C2 C1 C7 0.0(7) . . . . ? C28 C2 C1 C6 -175.1(5) . . . . ? C28 C2 C3B C14B 12.4(16) . . . . ? C28 C2 C3B C4B 178.8(9) . . . . ? C28 C2 C3A C4A 169.8(11) . . . . ? C28 C2 C3A C14A -9.3(16) . . . . ? C21B C5B C4B C3B -166.6(15) . . . . ? C21B C5B C4B C30B 20(2) . . . . ? C7 C1 C6 C32 6.7(8) . . . . ? C7 C1 C6 C5B 175.6(8) . . . . ? C7 C1 C6 C5A -163.9(9) . . . . ? C32 C6 C5B C21B -21.0(18) . . . . ? C32 C6 C5B C4B 169.4(10) . . . . ? C32 C6 C5A C4A 179.7(10) . . . . ? C32 C6 C5A C21A 5(2) . . . . ? C6 C1 C7 O1 89.0(6) . . . . ? C6 C5B C4B C3B 3.2(19) . . . . ? C6 C5B C4B C30B -170.5(14) . . . . ? C6 C5A C21A O3A 62(2) . . . . ? C33 C32 C6 C1 88.3(7) . . . . ? C33 C32 C6 C5B -80.1(9) . . . . ? C33 C32 C6 C5A -100.9(10) . . . . ? C3B C2 C1 C7 -170.6(8) . . . . ? C3B C2 C1 C6 14.3(10) . . . . ? C3B C2 C28 C29 79.1(10) . . . . ? C3B C2 C3A C4A -100(4) . . . . ? C3B C2 C3A C14A 81(4) . . . . ? C3B C14B O2B C15 -163.3(16) . . . . ? C5B C21B O3B C22B -163.8(15) . . . . ? C5B C6 C5A C4A 78(5) . . . . ? C5B C6 C5A C21A -97(6) . . . . ? C14B C3B C4B C5B 168.8(13) . . . . ? C14B C3B C4B C30B -18(2) . . . . ? C4A C3A C14A O2A -92(2) . . . . ? C4A C5A C21A O3A -113.0(18) . . . . ? C30A C4A C3A C2 174.5(12) . . . . ? C30A C4A C3A C14A -6(2) . . . . ? C30A C4A C5A C6 -170.0(13) . . . . ? C30A C4A C5A C21A 5(2) . . . . ? C31B C30B C4B C3B 87.2(17) . . . . ? C31B C30B C4B C5B -99.2(16) . . . . ? C4B C3B C14B O2B -89.2(17) . . . . ? C24B C25B C26B C27B -1(2) . . . . ? C3A C2 C1 C7 168.4(9) . . . . ? C3A C2 C1 C6 -6.8(11) . . . . ? C3A C2 C28 C29 99.8(10) . . . . ? C3A C2 C3B C14B -88(4) . . . . ? C3A C2 C3B C4B 79(4) . . . . ? C3A C4A C30A C31A -92.4(17) . . . . ? C3A C4A C5A C6 3.9(19) . . . . ? C3A C4A C5A C21A 178.7(17) . . . . ? C5A C6 C5B C21B 68(5) . . . . ? C5A C6 C5B C4B -102(5) . . . . ? C5A C4A C30A C31A 81.4(18) . . . . ? C5A C4A C3A C2 0.5(19) . . . . ? C5A C4A C3A C14A 179.6(13) . . . . ? C21A O3A C22A C27A -11(3) . . . . ? C21A O3A C22A C23A 171.8(17) . . . . ? O3B C22B C27B C26B -169.5(17) . . . . ? O3B C22B C23B C24B 163.7(16) . . . . ? O3B C21B C5B C6 82.4(15) . . . . ? O3B C21B C5B C4B -107.8(17) . . . . ? C22A O3A C21A C5A 172.4(16) . . . . ? C22A C27A C26A C25A 6(2) . . . . ? C27A C22A C23A C24A 14(3) . . . . ? C27A C26A C25A C24A 3(2) . . . . ? C27A C26A C25A I3A 177.7(11) . . . . ? C26A C25A C24A C23A -4.0(19) . . . . ? C25A C24A C23A C22A -5(2) . . . . ? C23A C22A C27A C26A -15(3) . . . . ? I3A C25A C24A C23A -178.7(11) . . . . ? C14A O2A C15 C20 9(3) . . . . ? C14A O2A C15 C16 -180(2) . . . . ? C14A O2A C15 O2B -75(12) . . . . ? O2B C15 C20 C19 -171.4(13) . . . . ? O2B C15 C16 C17 173.5(13) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.021 0.500 0.000 443 36 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962440'