#------------------------------------------------------------------------------ #$Date: 2016-03-26 14:43:29 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180274 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/60/7116079.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7116079 loop_ _publ_author_name 'Sebastien Goudedranche' 'David Pierrot' 'Thierry Constantieux' 'Damien Bonne' 'Jean Rodriguez' _publ_section_title ; A temporary-bridge strategy for enantioselective organocatalyzed synthesis of aza-seven-membered rings ; _journal_name_full Chem.Commun. _journal_page_first 15605 _journal_paper_doi 10.1039/C4cc07731H _journal_volume 50 _journal_year 2014 _chemical_absolute_configuration ad _chemical_formula_moiety '2(C21 H21 Cl N2 O5)' _chemical_formula_sum 'C42 H42 Cl2 N4 O10' _chemical_formula_weight 833.69 _chemical_melting_point 471 _chemical_name_systematic (1R,2S,3R,5S)-6-(4-chlorophenyl)-1-hydroxy-2-isopropyl-3-(4-nitrophenyl)-8-oxa-6-azabicyclo[3.2.1]octan-7-one _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date ; 'Tue Apr 15 17:14:35 2014' ; _audit_creation_method ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 7.85187(17) _cell_length_b 19.3756(4) _cell_length_c 26.7779(6) _cell_measurement_reflns_used 6029 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 73.6850 _cell_measurement_theta_min 4.8330 _cell_volume 4073.85(15) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.3048 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_details ; 1 omega -70.00 -2.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.5364 125.0000 -150.0000 68 2 omega -70.00 19.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.5364 77.0000 30.0000 89 3 omega 37.00 91.00 1.0000 17.5000 omega____ theta____ kappa____ phi______ frames - 107.1501 -30.0000 90.0000 54 4 omega 49.00 98.00 1.0000 17.5000 omega____ theta____ kappa____ phi______ frames - 107.1501 -45.0000 0.0000 49 5 omega 38.00 136.00 1.0000 17.5000 omega____ theta____ kappa____ phi______ frames - 107.1501 -61.0000 -180.0000 98 6 omega 36.00 82.00 1.0000 17.5000 omega____ theta____ kappa____ phi______ frames - 107.1501 -45.0000 -90.0000 46 7 omega 35.00 136.00 1.0000 17.5000 omega____ theta____ kappa____ phi______ frames - 107.1501 -77.0000 90.0000 101 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1536279000 _diffrn_orient_matrix_UB_12 -0.0485903000 _diffrn_orient_matrix_UB_13 -0.0071723000 _diffrn_orient_matrix_UB_21 -0.1020309000 _diffrn_orient_matrix_UB_22 0.0595979000 _diffrn_orient_matrix_UB_23 -0.0234472000 _diffrn_orient_matrix_UB_31 0.0670114000 _diffrn_orient_matrix_UB_32 -0.0201993000 _diffrn_orient_matrix_UB_33 -0.0520440000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_unetI/netI 0.0420 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.967 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 12523 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.954 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.645 _diffrn_reflns_theta_min 4.013 _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.965 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73740 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.359 _exptl_crystal_F_000 1744 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane' _exptl_crystal_size_max .26 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .06 _refine_diff_density_max 0.469 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.038 _refine_ls_abs_structure_details ; Flack x determined using 2784 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.012(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 529 _refine_ls_number_reflns 7842 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0470 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.4594P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1299 _refine_ls_wR_factor_ref 0.1372 _reflns_Friedel_coverage 0.751 _reflns_Friedel_fraction_full 0.987 _reflns_Friedel_fraction_max 0.937 _reflns_number_gt 7073 _reflns_number_total 7842 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4cc07731h2.cif _cod_data_source_block sg783 _cod_original_cell_volume 4073.84(15) _cod_database_code 7116079 #BEGIN Tags that were not found in dictionaries: _shelxl_version_number 2013-4 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _symmetry_space_group_name_h-m_alt 'P 21 21 21' _reflns_odcompleteness_completeness 98.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C10(H10), C31(H31), C33(H33), C12(H12), C9(H9), C30(H30), C13(H13), C34(H34) 2.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C32(H32A,H32B) 2.c Aromatic/amide H refined with riding coordinates: C42(H42), C20(H20), C21(H21), C41(H41), C38(H38), C17(H17), C39(H39), C2(H2A), C27(H27), C24(H24), C3(H3), C6(H6), C18(H18), C23(H23), C5(H5), C26(H26) 2.d Idealised Me refined as rotating group: C35(H35A,H35B,H35C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C36(H36A,H36B, H36C) 2.e Idealised tetrahedral OH refined as rotating group: O7(H7), O2(H2) ; _shelx_res_file ; TITL CF solution in P212121 CELL 1.54184 7.851869 19.375595 26.777861 90 90 90 ZERR 4 0.000167 0.000407 0.000579 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 168 168 8 16 40 L.S. 8 PLAN 25 BOND $h fmap 2 acta REM sg783.hkl WGHT 0.077100 0.459400 FVAR 3.80002 CL1 3 0.359193 0.776820 0.685110 11.00000 0.13098 0.06484 = 0.13151 -0.03826 0.02651 -0.00032 CL2 3 0.030552 0.782713 0.558503 11.00000 0.20135 0.07796 = 0.12042 0.04091 0.03533 -0.00039 O1 5 0.710545 0.468488 0.516204 11.00000 0.04356 0.07724 = 0.05851 -0.01584 0.00586 0.00048 O6 5 -0.243438 0.468654 0.733077 11.00000 0.04845 0.06766 = 0.05918 0.00861 0.00907 0.00632 O8 5 -0.059199 0.438934 0.617607 11.00000 0.06390 0.05761 = 0.04642 -0.00598 -0.00270 -0.00022 O3 5 0.523134 0.438299 0.630534 11.00000 0.06687 0.05440 = 0.04825 0.00454 -0.00497 0.00658 N1 4 0.550446 0.525564 0.572268 11.00000 0.05042 0.05178 = 0.04093 -0.00161 -0.00062 0.00338 O7 5 -0.263760 0.365035 0.691942 11.00000 0.05683 0.06358 = 0.07722 0.01763 -0.01482 -0.01423 AFIX 147 H7 2 -0.341932 0.380265 0.674886 11.00000 -1.50000 AFIX 0 O2 5 0.727459 0.363603 0.557242 11.00000 0.05810 0.06877 = 0.07972 -0.02232 -0.01956 0.02233 AFIX 147 H2 2 0.810515 0.379770 0.571656 11.00000 -1.50000 AFIX 0 N3 4 -0.097540 0.528073 0.674256 11.00000 0.05017 0.05211 = 0.04182 -0.00161 0.00020 0.00334 C7 1 0.556727 0.459827 0.588788 11.00000 0.04378 0.05202 = 0.04726 -0.00345 -0.00594 0.00454 C28 1 -0.097402 0.461141 0.658565 11.00000 0.04304 0.05321 = 0.04749 -0.00048 -0.00485 0.00275 C22 1 -0.062949 0.588041 0.646084 11.00000 0.04708 0.05238 = 0.04660 -0.00102 -0.00480 0.00208 C8 1 0.619515 0.415630 0.544120 11.00000 0.04715 0.05651 = 0.05299 -0.00845 -0.00309 0.00915 C10 1 0.357105 0.449563 0.496432 11.00000 0.04590 0.05448 = 0.03877 -0.00140 0.00165 0.00190 AFIX 13 H10 2 0.287197 0.458544 0.526045 11.00000 -1.20000 AFIX 0 C31 1 0.112509 0.453412 0.748449 11.00000 0.05147 0.05933 = 0.03879 0.00215 0.00044 0.00070 AFIX 13 H31 2 0.182760 0.463361 0.719068 11.00000 -1.20000 AFIX 0 C29 1 -0.155309 0.417442 0.704222 11.00000 0.04627 0.05662 = 0.05040 0.00307 0.00036 -0.00060 C1 1 0.501049 0.585009 0.599560 11.00000 0.04634 0.04987 = 0.04586 -0.00235 -0.00226 0.00047 C37 1 0.233505 0.440579 0.791374 11.00000 0.04872 0.05692 = 0.04031 -0.00029 0.00075 -0.00233 N4 4 0.580794 0.411280 0.910581 11.00000 0.09808 0.05989 = 0.05787 -0.00264 -0.02484 0.00876 C33 1 -0.144028 0.528398 0.727779 11.00000 0.05521 0.06054 = 0.04762 -0.00010 0.00824 0.01097 AFIX 13 H33 2 -0.208794 0.569898 0.736555 11.00000 -1.20000 AFIX 0 C40 1 0.459015 0.421954 0.869589 11.00000 0.06825 0.05479 = 0.04383 -0.00392 -0.01256 0.00376 C12 1 0.604763 0.526853 0.519440 11.00000 0.04737 0.06141 = 0.04799 -0.00388 0.00573 -0.00487 AFIX 13 H12 2 0.667523 0.569219 0.511630 11.00000 -1.20000 AFIX 0 C42 1 0.178406 0.413815 0.837024 11.00000 0.05494 0.07053 = 0.04518 0.00364 0.00467 -0.00625 AFIX 43 H42 2 0.064272 0.402300 0.841115 11.00000 -1.20000 AFIX 0 O9 5 0.728647 0.429283 0.904216 11.00000 0.07892 0.09995 = 0.09574 -0.00042 -0.03842 0.00080 C16 1 0.236770 0.430623 0.454527 11.00000 0.04631 0.05343 = 0.04303 0.00048 -0.00122 0.00009 C9 1 0.477875 0.388907 0.509568 11.00000 0.04600 0.05439 = 0.04998 -0.00959 -0.00406 0.00447 AFIX 13 H9 2 0.534333 0.376231 0.478244 11.00000 -1.20000 AFIX 0 C20 1 -0.051335 0.416938 0.424186 11.00000 0.05212 0.05994 = 0.06100 0.00241 -0.00833 -0.00209 AFIX 43 H20 2 -0.168180 0.419747 0.429496 11.00000 -1.20000 AFIX 0 C30 1 -0.002150 0.390985 0.734680 11.00000 0.04984 0.05604 = 0.04634 0.00404 -0.00313 0.00074 AFIX 13 H30 2 -0.046131 0.371334 0.765839 11.00000 -1.20000 AFIX 0 N2 4 -0.107828 0.380780 0.338524 11.00000 0.09939 0.06826 = 0.07148 -0.00281 -0.03261 -0.00960 C21 1 0.062826 0.433918 0.461685 11.00000 0.04795 0.05820 = 0.04862 0.00069 -0.00101 0.00279 AFIX 43 H21 2 0.021077 0.447937 0.492562 11.00000 -1.20000 AFIX 0 C41 1 0.290119 0.404143 0.876154 11.00000 0.07889 0.06276 = 0.04159 0.00291 0.00162 -0.00080 AFIX 43 H41 2 0.252499 0.385994 0.906354 11.00000 -1.20000 AFIX 0 C19 1 0.012637 0.395876 0.379023 11.00000 0.06749 0.05358 = 0.05205 0.00127 -0.01395 -0.00392 C11 1 0.454050 0.517099 0.484417 11.00000 0.05754 0.06095 = 0.04228 0.00336 0.00304 -0.00290 AFIX 23 H11A 2 0.494304 0.515668 0.450185 11.00000 -1.20000 H11B 2 0.377139 0.556020 0.487652 11.00000 -1.20000 AFIX 0 O10 5 0.530008 0.386043 0.948727 11.00000 0.13667 0.11865 = 0.05641 0.01894 -0.02575 -0.00121 C38 1 0.403075 0.458021 0.786624 11.00000 0.05402 0.06578 = 0.04397 0.00702 -0.00023 -0.00255 AFIX 43 H38 2 0.441498 0.476358 0.756571 11.00000 -1.20000 AFIX 0 C4 1 0.413560 0.702761 0.651782 11.00000 0.07728 0.05645 = 0.08259 -0.01873 0.00404 0.00124 O5 5 -0.050540 0.365811 0.297737 11.00000 0.14080 0.13127 = 0.06444 -0.01820 -0.02986 -0.01781 C32 1 0.012052 0.520458 0.760576 11.00000 0.06603 0.06082 = 0.04284 -0.00400 0.00321 0.00106 AFIX 23 H32A 2 -0.022844 0.519581 0.795319 11.00000 -1.20000 H32B 2 0.086075 0.560009 0.755878 11.00000 -1.20000 AFIX 0 C17 1 0.297128 0.409545 0.407839 11.00000 0.05559 0.08730 = 0.04935 -0.00968 0.00293 0.00480 AFIX 43 H17 2 0.413868 0.407341 0.402191 11.00000 -1.20000 AFIX 0 C39 1 0.517784 0.448952 0.825449 11.00000 0.05397 0.06401 = 0.05247 0.00383 -0.00472 -0.00362 AFIX 43 H39 2 0.631787 0.460876 0.821668 11.00000 -1.20000 AFIX 0 C13 1 0.377485 0.323771 0.526281 11.00000 0.07078 0.05271 = 0.07044 -0.00371 -0.00724 -0.00062 AFIX 13 H13 2 0.280890 0.320960 0.503194 11.00000 -1.20000 AFIX 0 C25 1 -0.009367 0.707098 0.591889 11.00000 0.09952 0.05992 = 0.07396 0.01469 0.00119 -0.00223 O4 5 -0.260012 0.385938 0.346447 11.00000 0.08166 0.13408 = 0.12269 -0.01713 -0.04674 -0.00525 C2 1 0.456733 0.581547 0.649474 11.00000 0.07899 0.05635 = 0.05426 0.00087 0.01112 0.00580 AFIX 43 H2A 2 0.455819 0.539178 0.665792 11.00000 -1.20000 AFIX 0 C27 1 -0.088314 0.652391 0.667097 11.00000 0.11183 0.05422 = 0.05784 -0.00210 0.00935 0.00213 AFIX 43 H27 2 -0.124533 0.655654 0.700079 11.00000 -1.20000 AFIX 0 C24 1 0.017277 0.644450 0.570244 11.00000 0.10561 0.07915 = 0.05353 0.00416 0.01415 -0.01064 AFIX 43 H24 2 0.053583 0.642101 0.537229 11.00000 -1.20000 AFIX 0 C3 1 0.413962 0.640682 0.675067 11.00000 0.09012 0.07077 = 0.05760 -0.01319 0.01401 0.00207 AFIX 43 H3 2 0.385044 0.637989 0.708690 11.00000 -1.20000 AFIX 0 C34 1 0.092687 0.331906 0.705672 11.00000 0.07704 0.06259 = 0.06410 -0.00643 -0.00746 0.01399 AFIX 13 H34 2 0.094711 0.344392 0.670213 11.00000 -1.20000 AFIX 0 C6 1 0.500521 0.648742 0.576237 11.00000 0.09871 0.05284 = 0.05661 0.00562 0.00530 0.00226 AFIX 43 H6 2 0.529108 0.651952 0.542614 11.00000 -1.20000 AFIX 0 C18 1 0.185586 0.391911 0.369901 11.00000 0.07586 0.07993 = 0.04399 -0.00791 -0.00099 0.00310 AFIX 43 H18 2 0.226162 0.377699 0.338935 11.00000 -1.20000 AFIX 0 C23 1 -0.009016 0.584593 0.596764 11.00000 0.08986 0.06103 = 0.05398 -0.00292 0.01274 -0.00606 AFIX 43 H23 2 0.009262 0.541972 0.581717 11.00000 -1.20000 AFIX 0 C35 1 0.272944 0.318362 0.721840 11.00000 0.08556 0.10042 = 0.11741 -0.03859 -0.01428 0.03385 AFIX 137 H35A 2 0.338442 0.359988 0.718802 11.00000 -1.50000 H35B 2 0.321809 0.283179 0.701058 11.00000 -1.50000 H35C 2 0.273701 0.303268 0.755986 11.00000 -1.50000 AFIX 0 C5 1 0.457863 0.707661 0.602498 11.00000 0.11297 0.04720 = 0.08739 0.00148 0.01035 0.00047 AFIX 43 H5 2 0.459266 0.750433 0.586744 11.00000 -1.20000 AFIX 0 C26 1 -0.060767 0.711844 0.639934 11.00000 0.13088 0.05335 = 0.08251 -0.00031 0.01573 0.00256 AFIX 43 H26 2 -0.077432 0.754848 0.654564 11.00000 -1.20000 AFIX 0 C14 1 0.298832 0.327141 0.576998 11.00000 0.12514 0.07881 = 0.08899 -0.00223 0.01646 -0.03612 AFIX 137 H14A 2 0.386927 0.328412 0.601840 11.00000 -1.50000 H14B 2 0.228765 0.287175 0.582186 11.00000 -1.50000 H14C 2 0.230241 0.368002 0.579570 11.00000 -1.50000 AFIX 0 C15 1 0.475876 0.257831 0.517970 11.00000 0.11106 0.05832 = 0.15703 -0.01683 -0.02164 0.01445 AFIX 137 H15A 2 0.523651 0.257968 0.484970 11.00000 -1.50000 H15B 2 0.400740 0.219052 0.521515 11.00000 -1.50000 H15C 2 0.565810 0.254536 0.542140 11.00000 -1.50000 AFIX 0 C36 1 -0.003101 0.263191 0.710691 11.00000 0.10240 0.06507 = 0.19325 -0.02822 -0.01371 0.00968 AFIX 137 H36A 2 -0.021948 0.253303 0.745383 11.00000 -1.50000 H36B 2 0.063389 0.226882 0.696030 11.00000 -1.50000 H36C 2 -0.110649 0.266413 0.693799 11.00000 -1.50000 AFIX 0 HKLF 4 REM CF solution in P212121 REM R1 = 0.0470 for 7073 Fo > 4sig(Fo) and 0.0524 for all 7842 data REM 529 parameters refined using 0 restraints END WGHT 0.0771 0.4595 REM Highest difference peak 0.469, deepest hole -0.353, 1-sigma level 0.038 Q1 1 0.1040 0.7568 0.5377 11.00000 0.05 0.47 Q2 1 -0.0970 0.7740 0.5432 11.00000 0.05 0.33 Q3 1 0.4983 0.7766 0.6947 11.00000 0.05 0.27 Q4 1 0.3314 0.7454 0.7059 11.00000 0.05 0.23 Q5 1 0.2152 0.3377 0.6850 11.00000 0.05 0.22 Q6 1 0.0465 0.3398 0.3058 11.00000 0.05 0.19 Q7 1 0.0261 0.5833 0.6287 11.00000 0.05 0.16 Q8 1 0.4065 0.2737 0.4830 11.00000 0.05 0.16 Q9 1 0.0461 0.7803 0.5721 11.00000 0.05 0.15 Q10 1 0.6535 0.4471 0.6236 11.00000 0.05 0.14 Q11 1 0.2988 0.4570 0.7933 11.00000 0.05 0.14 Q12 1 0.4543 0.5403 0.5769 11.00000 0.05 0.14 Q13 1 -0.0090 0.2848 0.6756 11.00000 0.05 0.14 Q14 1 0.0459 0.6776 0.5802 11.00000 0.05 0.13 Q15 1 0.4968 0.6596 0.6695 11.00000 0.05 0.13 Q16 1 -0.1986 0.3207 0.7642 11.00000 0.05 0.13 Q17 1 0.4197 0.3839 0.4163 11.00000 0.05 0.13 Q18 1 0.4124 0.3924 0.9555 11.00000 0.05 0.13 Q19 1 0.0215 0.7024 0.6210 11.00000 0.05 0.13 Q20 1 0.2172 0.4793 0.5247 11.00000 0.05 0.12 Q21 1 0.1214 0.3195 0.7333 11.00000 0.05 0.12 Q22 1 0.3487 0.4335 0.8788 11.00000 0.05 0.12 Q23 1 0.2716 0.3793 0.5926 11.00000 0.05 0.12 Q24 1 0.5165 0.5767 0.6279 11.00000 0.05 0.12 Q25 1 0.5676 0.5062 0.5832 11.00000 0.05 0.12 ; _shelx_res_checksum 79513 #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn Cl1 Cl 0.3592(2) 0.77682(7) 0.68511(7) 0.1091(5) Uani 1 1 d . Cl2 Cl 0.0306(4) 0.78271(8) 0.55850(7) 0.1332(8) Uani 1 1 d . O1 O 0.7105(3) 0.46849(15) 0.51620(10) 0.0598(6) Uani 1 1 d . O6 O -0.2434(3) 0.46865(14) 0.73308(10) 0.0584(6) Uani 1 1 d . O8 O -0.0592(3) 0.43893(13) 0.61761(9) 0.0560(5) Uani 1 1 d . O3 O 0.5231(3) 0.43830(12) 0.63053(9) 0.0565(5) Uani 1 1 d . N1 N 0.5504(3) 0.52556(14) 0.57227(9) 0.0477(5) Uani 1 1 d . O7 O -0.2638(3) 0.36503(14) 0.69194(11) 0.0659(7) Uani 1 1 d . H7 H -0.3419 0.3803 0.6749 0.099 Uiso 1 1 calc GR O2 O 0.7275(4) 0.36360(15) 0.55724(11) 0.0689(7) Uani 1 1 d . H2 H 0.8105 0.3798 0.5717 0.103 Uiso 1 1 calc GR N3 N -0.0975(3) 0.52807(14) 0.67426(10) 0.0480(5) Uani 1 1 d . C7 C 0.5567(4) 0.45983(16) 0.58879(12) 0.0477(6) Uani 1 1 d . C28 C -0.0974(4) 0.46114(17) 0.65856(12) 0.0479(6) Uani 1 1 d . C22 C -0.0629(4) 0.58804(17) 0.64608(12) 0.0487(6) Uani 1 1 d . C8 C 0.6195(4) 0.41563(18) 0.54412(13) 0.0522(7) Uani 1 1 d . C10 C 0.3571(4) 0.44956(17) 0.49643(11) 0.0464(6) Uani 1 1 d . H10 H 0.2872 0.4585 0.5260 0.056 Uiso 1 1 calc R C31 C 0.1125(4) 0.45341(18) 0.74845(11) 0.0499(7) Uani 1 1 d . H31 H 0.1828 0.4634 0.7191 0.060 Uiso 1 1 calc R C29 C -0.1553(4) 0.41744(18) 0.70422(12) 0.0511(7) Uani 1 1 d . C1 C 0.5010(4) 0.58501(17) 0.59956(12) 0.0474(6) Uani 1 1 d . C37 C 0.2335(4) 0.44058(17) 0.79137(11) 0.0487(6) Uani 1 1 d . N4 N 0.5808(6) 0.41128(18) 0.91058(13) 0.0719(9) Uani 1 1 d . C33 C -0.1440(5) 0.52840(19) 0.72778(12) 0.0545(7) Uani 1 1 d . H33 H -0.2088 0.5699 0.7366 0.065 Uiso 1 1 calc R C40 C 0.4590(5) 0.42195(18) 0.86959(12) 0.0556(7) Uani 1 1 d . C12 C 0.6048(4) 0.52685(19) 0.51944(12) 0.0523(7) Uani 1 1 d . H12 H 0.6675 0.5692 0.5116 0.063 Uiso 1 1 calc R C42 C 0.1784(5) 0.4138(2) 0.83702(12) 0.0569(8) Uani 1 1 d . H42 H 0.0643 0.4023 0.8411 0.068 Uiso 1 1 calc R O9 O 0.7286(5) 0.4293(2) 0.90422(14) 0.0915(10) Uani 1 1 d . C16 C 0.2368(4) 0.43062(16) 0.45453(11) 0.0476(6) Uani 1 1 d . C9 C 0.4779(4) 0.38891(17) 0.50957(12) 0.0501(7) Uani 1 1 d . H9 H 0.5343 0.3762 0.4782 0.060 Uiso 1 1 calc R C20 C -0.0513(5) 0.41694(19) 0.42419(14) 0.0577(8) Uani 1 1 d . H20 H -0.1682 0.4197 0.4295 0.069 Uiso 1 1 calc R C30 C -0.0021(4) 0.39099(17) 0.73468(12) 0.0507(7) Uani 1 1 d . H30 H -0.0461 0.3713 0.7658 0.061 Uiso 1 1 calc R N2 N -0.1078(6) 0.3808(2) 0.33852(15) 0.0797(11) Uani 1 1 d . C21 C 0.0628(4) 0.43392(18) 0.46168(12) 0.0516(7) Uani 1 1 d . H21 H 0.0211 0.4479 0.4926 0.062 Uiso 1 1 calc R C41 C 0.2901(6) 0.4041(2) 0.87615(12) 0.0611(8) Uani 1 1 d . H41 H 0.2525 0.3860 0.9064 0.073 Uiso 1 1 calc R C19 C 0.0126(5) 0.39588(18) 0.37902(13) 0.0577(8) Uani 1 1 d . C11 C 0.4541(5) 0.51710(19) 0.48442(12) 0.0536(7) Uani 1 1 d . H11A H 0.4943 0.5157 0.4502 0.064 Uiso 1 1 calc R H11B H 0.3771 0.5560 0.4877 0.064 Uiso 1 1 calc R O10 O 0.5300(7) 0.3860(2) 0.94873(12) 0.1039(13) Uani 1 1 d . C38 C 0.4031(4) 0.45802(19) 0.78662(13) 0.0546(7) Uani 1 1 d . H38 H 0.4415 0.4764 0.7566 0.066 Uiso 1 1 calc R C4 C 0.4136(6) 0.7028(2) 0.65178(18) 0.0721(11) Uani 1 1 d . O5 O -0.0505(7) 0.3658(3) 0.29774(14) 0.1122(14) Uani 1 1 d . C32 C 0.0121(5) 0.52046(19) 0.76058(12) 0.0566(7) Uani 1 1 d . H32A H -0.0228 0.5196 0.7953 0.068 Uiso 1 1 calc R H32B H 0.0861 0.5600 0.7559 0.068 Uiso 1 1 calc R C17 C 0.2971(5) 0.4095(2) 0.40784(14) 0.0641(9) Uani 1 1 d . H17 H 0.4139 0.4073 0.4022 0.077 Uiso 1 1 calc R C39 C 0.5178(5) 0.44895(19) 0.82545(13) 0.0568(7) Uani 1 1 d . H39 H 0.6318 0.4609 0.8217 0.068 Uiso 1 1 calc R C13 C 0.3775(6) 0.3238(2) 0.52628(16) 0.0646(9) Uani 1 1 d . H13 H 0.2809 0.3210 0.5032 0.078 Uiso 1 1 calc R C25 C -0.0094(7) 0.7071(2) 0.59189(18) 0.0778(12) Uani 1 1 d . O4 O -0.2600(6) 0.3859(3) 0.34645(18) 0.1128(14) Uani 1 1 d . C2 C 0.4567(6) 0.5815(2) 0.64947(14) 0.0632(9) Uani 1 1 d . H2A H 0.4558 0.5392 0.6658 0.076 Uiso 1 1 calc R C27 C -0.0883(7) 0.6524(2) 0.66710(16) 0.0746(12) Uani 1 1 d . H27 H -0.1245 0.6557 0.7001 0.090 Uiso 1 1 calc R C24 C 0.0173(7) 0.6445(2) 0.57024(16) 0.0794(12) Uani 1 1 d . H24 H 0.0536 0.6421 0.5372 0.095 Uiso 1 1 calc R C3 C 0.4140(6) 0.6407(2) 0.67507(16) 0.0728(11) Uani 1 1 d . H3 H 0.3850 0.6380 0.7087 0.087 Uiso 1 1 calc R C34 C 0.0927(6) 0.3319(2) 0.70567(16) 0.0679(10) Uani 1 1 d . H34 H 0.0947 0.3444 0.6702 0.081 Uiso 1 1 calc R C6 C 0.5005(7) 0.6487(2) 0.57624(15) 0.0694(10) Uani 1 1 d . H6 H 0.5291 0.6520 0.5426 0.083 Uiso 1 1 calc R C18 C 0.1856(6) 0.3919(2) 0.36990(14) 0.0666(9) Uani 1 1 d . H18 H 0.2262 0.3777 0.3389 0.080 Uiso 1 1 calc R C23 C -0.0090(6) 0.5846(2) 0.59676(15) 0.0683(10) Uani 1 1 d . H23 H 0.0093 0.5420 0.5817 0.082 Uiso 1 1 calc R C35 C 0.2729(8) 0.3184(3) 0.7218(2) 0.1011(19) Uani 1 1 d . H35A H 0.3384 0.3600 0.7188 0.152 Uiso 1 1 calc GR H35B H 0.3218 0.2832 0.7011 0.152 Uiso 1 1 calc GR H35C H 0.2737 0.3033 0.7560 0.152 Uiso 1 1 calc GR C5 C 0.4579(8) 0.7077(2) 0.6025(2) 0.0825(13) Uani 1 1 d . H5 H 0.4593 0.7504 0.5867 0.099 Uiso 1 1 calc R C26 C -0.0608(9) 0.7118(2) 0.6399(2) 0.0889(15) Uani 1 1 d . H26 H -0.0774 0.7548 0.6546 0.107 Uiso 1 1 calc R C14 C 0.2988(9) 0.3271(3) 0.5770(2) 0.0976(17) Uani 1 1 d . H14A H 0.3869 0.3284 0.6018 0.146 Uiso 1 1 calc GR H14B H 0.2288 0.2872 0.5822 0.146 Uiso 1 1 calc GR H14C H 0.2302 0.3680 0.5796 0.146 Uiso 1 1 calc GR C15 C 0.4759(10) 0.2578(3) 0.5180(3) 0.109(2) Uani 1 1 d . H15A H 0.5237 0.2580 0.4850 0.163 Uiso 1 1 calc GR H15B H 0.4007 0.2191 0.5215 0.163 Uiso 1 1 calc GR H15C H 0.5658 0.2545 0.5421 0.163 Uiso 1 1 calc GR C36 C -0.0031(9) 0.2632(3) 0.7107(3) 0.120(2) Uani 1 1 d . H36A H -0.0219 0.2533 0.7454 0.180 Uiso 1 1 calc GR H36B H 0.0634 0.2269 0.6960 0.180 Uiso 1 1 calc GR H36C H -0.1106 0.2664 0.6938 0.180 Uiso 1 1 calc GR loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1310(12) 0.0648(6) 0.1315(12) -0.0383(7) 0.0265(10) -0.0003(7) Cl2 0.201(2) 0.0780(8) 0.1204(12) 0.0409(8) 0.0353(13) -0.0004(11) O1 0.0436(11) 0.0772(15) 0.0585(13) -0.0158(12) 0.0059(10) 0.0005(11) O6 0.0485(11) 0.0677(14) 0.0592(13) 0.0086(11) 0.0091(10) 0.0063(11) O8 0.0639(13) 0.0576(12) 0.0464(12) -0.0060(9) -0.0027(10) -0.0002(11) O3 0.0669(14) 0.0544(12) 0.0483(12) 0.0045(9) -0.0050(10) 0.0066(11) N1 0.0504(12) 0.0518(13) 0.0409(12) -0.0016(10) -0.0006(10) 0.0034(11) O7 0.0568(13) 0.0636(14) 0.0772(17) 0.0176(12) -0.0148(12) -0.0142(12) O2 0.0581(14) 0.0688(15) 0.0797(17) -0.0223(13) -0.0196(13) 0.0223(12) N3 0.0502(13) 0.0521(13) 0.0418(12) -0.0016(10) 0.0002(10) 0.0033(11) C7 0.0438(14) 0.0520(15) 0.0473(16) -0.0035(12) -0.0059(12) 0.0045(12) C28 0.0430(14) 0.0532(16) 0.0475(16) -0.0005(12) -0.0049(12) 0.0027(12) C22 0.0471(14) 0.0524(16) 0.0466(15) -0.0010(12) -0.0048(12) 0.0021(13) C8 0.0471(15) 0.0565(17) 0.0530(16) -0.0084(14) -0.0031(13) 0.0092(14) C10 0.0459(14) 0.0545(16) 0.0388(13) -0.0014(11) 0.0017(11) 0.0019(13) C31 0.0515(16) 0.0593(17) 0.0388(14) 0.0022(12) 0.0004(12) 0.0007(14) C29 0.0463(15) 0.0566(16) 0.0504(16) 0.0031(13) 0.0004(12) -0.0006(14) C1 0.0463(14) 0.0499(15) 0.0459(15) -0.0024(12) -0.0023(12) 0.0005(12) C37 0.0487(15) 0.0569(16) 0.0403(14) -0.0003(12) 0.0008(12) -0.0023(13) N4 0.098(3) 0.0599(17) 0.0579(18) -0.0026(14) -0.0248(17) 0.0088(18) C33 0.0552(16) 0.0605(18) 0.0476(16) -0.0001(14) 0.0082(13) 0.0110(15) C40 0.0682(19) 0.0548(17) 0.0438(15) -0.0039(13) -0.0126(14) 0.0038(15) C12 0.0474(15) 0.0614(18) 0.0480(16) -0.0039(14) 0.0057(13) -0.0049(14) C42 0.0549(17) 0.071(2) 0.0452(16) 0.0036(14) 0.0047(13) -0.0062(16) O9 0.079(2) 0.100(2) 0.096(2) -0.0004(19) -0.0384(18) 0.0008(18) C16 0.0463(14) 0.0534(15) 0.0430(14) 0.0005(12) -0.0012(12) 0.0001(13) C9 0.0460(15) 0.0544(16) 0.0500(16) -0.0096(13) -0.0041(12) 0.0045(13) C20 0.0521(16) 0.0599(18) 0.0610(19) 0.0024(15) -0.0083(15) -0.0021(15) C30 0.0498(15) 0.0560(17) 0.0463(15) 0.0040(13) -0.0031(13) 0.0007(14) N2 0.099(3) 0.068(2) 0.071(2) -0.0028(16) -0.033(2) -0.0096(19) C21 0.0479(15) 0.0582(17) 0.0486(16) 0.0007(13) -0.0010(12) 0.0028(14) C41 0.079(2) 0.0628(19) 0.0416(16) 0.0029(14) 0.0016(15) -0.0008(17) C19 0.067(2) 0.0536(17) 0.0520(17) 0.0013(13) -0.0140(15) -0.0039(15) C11 0.0575(17) 0.0610(18) 0.0423(15) 0.0034(13) 0.0030(13) -0.0029(15) O10 0.137(3) 0.119(3) 0.0564(17) 0.0189(18) -0.026(2) -0.001(3) C38 0.0540(17) 0.0658(19) 0.0440(15) 0.0070(13) -0.0002(13) -0.0026(15) C4 0.077(3) 0.056(2) 0.083(3) -0.0187(18) 0.004(2) 0.0012(18) O5 0.141(4) 0.131(3) 0.064(2) -0.018(2) -0.030(2) -0.018(3) C32 0.0660(19) 0.0608(18) 0.0428(16) -0.0040(13) 0.0032(14) 0.0011(16) C17 0.0556(18) 0.087(3) 0.0493(18) -0.0097(17) 0.0029(14) 0.0048(18) C39 0.0540(17) 0.0640(19) 0.0525(17) 0.0038(14) -0.0047(14) -0.0036(15) C13 0.071(2) 0.0527(18) 0.070(2) -0.0037(16) -0.0072(18) -0.0006(17) C25 0.100(3) 0.060(2) 0.074(3) 0.0147(18) 0.001(2) -0.002(2) O4 0.082(2) 0.134(4) 0.123(3) -0.017(3) -0.047(2) -0.005(2) C2 0.079(2) 0.0563(18) 0.0543(19) 0.0009(14) 0.0111(17) 0.0058(18) C27 0.112(4) 0.0542(19) 0.058(2) -0.0021(16) 0.009(2) 0.002(2) C24 0.106(3) 0.079(3) 0.054(2) 0.0042(18) 0.014(2) -0.011(3) C3 0.090(3) 0.071(2) 0.058(2) -0.0132(18) 0.0140(19) 0.002(2) C34 0.077(2) 0.063(2) 0.064(2) -0.0064(17) -0.0075(19) 0.0140(19) C6 0.099(3) 0.0528(18) 0.057(2) 0.0056(15) 0.005(2) 0.002(2) C18 0.076(2) 0.080(2) 0.0440(17) -0.0079(16) -0.0010(16) 0.0031(19) C23 0.090(3) 0.061(2) 0.0540(19) -0.0029(15) 0.0127(19) -0.0061(19) C35 0.086(3) 0.100(4) 0.117(4) -0.039(3) -0.014(3) 0.034(3) C5 0.113(4) 0.0472(19) 0.087(3) 0.0015(18) 0.010(3) 0.000(2) C26 0.131(4) 0.053(2) 0.083(3) -0.0003(19) 0.016(3) 0.003(3) C14 0.125(5) 0.079(3) 0.089(3) -0.002(3) 0.016(3) -0.036(3) C15 0.111(4) 0.058(2) 0.157(6) -0.017(3) -0.022(4) 0.014(3) C36 0.102(4) 0.065(3) 0.193(8) -0.028(4) -0.014(5) 0.010(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 O1 C8 104.1(2) C33 O6 C29 104.3(2) C7 N1 C1 127.4(3) C7 N1 C12 108.6(3) C1 N1 C12 124.0(3) C29 O7 H7 109.5 C8 O2 H2 109.5 C28 N3 C22 128.2(3) C28 N3 C33 107.6(3) C22 N3 C33 124.2(3) O3 C7 N1 127.9(3) O3 C7 C8 125.8(3) N1 C7 C8 106.3(3) O8 C28 N3 127.9(3) O8 C28 C29 126.1(3) N3 C28 C29 106.0(3) C27 C22 N3 119.8(3) C27 C22 C23 118.3(3) C23 C22 N3 121.8(3) O1 C8 C7 99.4(3) O1 C8 C9 106.5(3) O2 C8 O1 110.3(3) O2 C8 C7 114.0(3) O2 C8 C9 110.9(3) C9 C8 C7 114.8(3) C16 C10 H10 107.1 C16 C10 C9 111.5(3) C16 C10 C11 111.0(3) C9 C10 H10 107.1 C11 C10 H10 107.1 C11 C10 C9 112.8(3) C37 C31 H31 106.8 C37 C31 C30 114.6(3) C37 C31 C32 107.3(3) C30 C31 H31 106.8 C30 C31 C32 114.0(3) C32 C31 H31 106.8 O6 C29 C28 100.8(3) O6 C29 C30 108.7(3) O7 C29 O6 110.1(3) O7 C29 C28 113.4(3) O7 C29 C30 111.5(3) C30 C29 C28 111.7(3) C2 C1 N1 121.8(3) C2 C1 C6 118.6(3) C6 C1 N1 119.5(3) C42 C37 C31 122.1(3) C38 C37 C31 119.7(3) C38 C37 C42 118.1(3) O9 N4 C40 118.2(4) O10 N4 C40 118.5(4) O10 N4 O9 123.3(4) O6 C33 N3 103.4(3) O6 C33 H33 111.3 O6 C33 C32 107.9(3) N3 C33 H33 111.3 N3 C33 C32 111.2(3) C32 C33 H33 111.3 C41 C40 N4 119.6(3) C39 C40 N4 118.5(4) C39 C40 C41 121.8(3) O1 C12 N1 102.5(3) O1 C12 H12 111.3 O1 C12 C11 108.8(3) N1 C12 H12 111.3 N1 C12 C11 111.3(3) C11 C12 H12 111.3 C37 C42 H42 119.4 C41 C42 C37 121.2(3) C41 C42 H42 119.4 C21 C16 C10 120.3(3) C21 C16 C17 118.2(3) C17 C16 C10 121.5(3) C8 C9 C10 108.9(3) C8 C9 H9 105.8 C8 C9 C13 117.9(3) C10 C9 H9 105.8 C10 C9 C13 111.8(3) C13 C9 H9 105.8 C21 C20 H20 120.9 C19 C20 H20 120.9 C19 C20 C21 118.2(3) C31 C30 H30 107.8 C31 C30 C34 114.2(3) C29 C30 C31 108.6(3) C29 C30 H30 107.8 C29 C30 C34 110.5(3) C34 C30 H30 107.8 O5 N2 C19 118.2(5) O5 N2 O4 122.6(4) O4 N2 C19 119.1(4) C16 C21 C20 121.9(3) C16 C21 H21 119.1 C20 C21 H21 119.1 C40 C41 H41 120.7 C42 C41 C40 118.7(3) C42 C41 H41 120.7 C20 C19 N2 118.3(4) C20 C19 C18 122.2(3) C18 C19 N2 119.4(4) C10 C11 H11A 109.4 C10 C11 H11B 109.4 C12 C11 C10 111.1(3) C12 C11 H11A 109.4 C12 C11 H11B 109.4 H11A C11 H11B 108.0 C37 C38 H38 119.1 C37 C38 C39 121.8(3) C39 C38 H38 119.1 C3 C4 Cl1 119.7(4) C3 C4 C5 120.3(4) C5 C4 Cl1 119.9(4) C31 C32 H32A 109.2 C31 C32 H32B 109.2 C33 C32 C31 112.0(3) C33 C32 H32A 109.2 C33 C32 H32B 109.2 H32A C32 H32B 107.9 C16 C17 H17 119.5 C18 C17 C16 120.9(3) C18 C17 H17 119.5 C40 C39 C38 118.4(3) C40 C39 H39 120.8 C38 C39 H39 120.8 C9 C13 H13 104.8 C14 C13 C9 115.9(3) C14 C13 H13 104.8 C14 C13 C15 112.5(5) C15 C13 C9 112.7(4) C15 C13 H13 104.8 C24 C25 Cl2 120.2(4) C26 C25 Cl2 119.0(4) C26 C25 C24 120.8(4) C1 C2 H2A 119.9 C3 C2 C1 120.1(4) C3 C2 H2A 119.9 C22 C27 H27 119.5 C26 C27 C22 121.1(4) C26 C27 H27 119.5 C25 C24 H24 119.7 C25 C24 C23 120.6(4) C23 C24 H24 119.7 C4 C3 C2 120.7(4) C4 C3 H3 119.7 C2 C3 H3 119.7 C30 C34 H34 107.9 C35 C34 C30 115.5(4) C35 C34 H34 107.9 C35 C34 C36 106.5(5) C36 C34 C30 110.9(4) C36 C34 H34 107.9 C1 C6 H6 119.7 C5 C6 C1 120.5(4) C5 C6 H6 119.7 C19 C18 C17 118.6(3) C19 C18 H18 120.7 C17 C18 H18 120.7 C22 C23 H23 120.1 C24 C23 C22 119.8(4) C24 C23 H23 120.1 C34 C35 H35A 109.5 C34 C35 H35B 109.5 C34 C35 H35C 109.5 H35A C35 H35B 109.5 H35A C35 H35C 109.5 H35B C35 H35C 109.5 C4 C5 C6 119.7(4) C4 C5 H5 120.2 C6 C5 H5 120.2 C25 C26 C27 119.5(4) C25 C26 H26 120.3 C27 C26 H26 120.3 C13 C14 H14A 109.5 C13 C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C13 C15 H15A 109.5 C13 C15 H15B 109.5 C13 C15 H15C 109.5 H15A C15 H15B 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C34 C36 H36A 109.5 C34 C36 H36B 109.5 C34 C36 H36C 109.5 H36A C36 H36B 109.5 H36A C36 H36C 109.5 H36B C36 H36C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C4 1.743(4) Cl2 C25 1.745(4) O1 C8 1.456(5) O1 C12 1.406(4) O6 C29 1.435(4) O6 C33 1.403(5) O8 C28 1.216(4) O3 C7 1.222(4) N1 C7 1.349(4) N1 C1 1.418(4) N1 C12 1.478(4) O7 H7 0.8200 O7 C29 1.365(4) O2 H2 0.8200 O2 C8 1.363(4) N3 C28 1.363(4) N3 C22 1.412(4) N3 C33 1.479(4) C7 C8 1.551(4) C28 C29 1.555(5) C22 C27 1.382(5) C22 C23 1.389(5) C8 C9 1.537(4) C10 H10 0.9800 C10 C16 1.512(4) C10 C9 1.551(4) C10 C11 1.548(5) C31 H31 0.9800 C31 C37 1.512(4) C31 C30 1.552(5) C31 C32 1.554(5) C29 C30 1.541(4) C1 C2 1.383(5) C1 C6 1.384(5) C37 C42 1.397(5) C37 C38 1.380(5) N4 C40 1.470(5) N4 O9 1.224(6) N4 O10 1.201(6) C33 H33 0.9800 C33 C32 1.516(5) C40 C41 1.382(6) C40 C39 1.372(5) C12 H12 0.9800 C12 C11 1.522(5) C42 H42 0.9300 C42 C41 1.379(5) C16 C21 1.381(5) C16 C17 1.398(5) C9 H9 0.9800 C9 C13 1.554(5) C20 H20 0.9300 C20 C21 1.386(5) C20 C19 1.372(6) C30 H30 0.9800 C30 C34 1.571(5) N2 C19 1.468(5) N2 O5 1.216(6) N2 O4 1.218(7) C21 H21 0.9300 C41 H41 0.9300 C19 C18 1.382(6) C11 H11A 0.9700 C11 H11B 0.9700 C38 H38 0.9300 C38 C39 1.387(5) C4 C3 1.355(7) C4 C5 1.368(7) C32 H32A 0.9700 C32 H32B 0.9700 C17 H17 0.9300 C17 C18 1.384(6) C39 H39 0.9300 C13 H13 0.9800 C13 C14 1.493(7) C13 C15 1.510(7) C25 C24 1.361(7) C25 C26 1.351(7) C2 H2A 0.9300 C2 C3 1.377(6) C27 H27 0.9300 C27 C26 1.379(7) C24 H24 0.9300 C24 C23 1.375(6) C3 H3 0.9300 C34 H34 0.9800 C34 C35 1.503(7) C34 C36 1.535(8) C6 H6 0.9300 C6 C5 1.382(6) C18 H18 0.9300 C23 H23 0.9300 C35 H35A 0.9600 C35 H35B 0.9600 C35 H35C 0.9600 C5 H5 0.9300 C26 H26 0.9300 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C36 H36A 0.9600 C36 H36B 0.9600 C36 H36C 0.9600