# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Olivier Maury' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Chantal Andraud' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Christophe Aronica' '' '' 'Pierre-Antoine Bouit' '' '' 'Laure Guy' '' '' 'Alexandre Martinez' '' '' _publ_contact_author_name 'Olivier Maury' _publ_contact_author_email OLIVIER.MAURY@ENS-LYON.FR _publ_section_title ; Diastereoselective supramolecular ion-pairing between TRISPHAT anion and pro-chiral heptamethine cyanine dye. ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' # Attachment '1,TRISPHAT.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 717753' _audit_creation_date 07-09-21 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'import in P -1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.673(5) _cell_length_b 14.213(5) _cell_length_c 20.031(5) _cell_angle_alpha 73.329(5) _cell_angle_beta 89.059(5) _cell_angle_gamma 62.217(5) _cell_volume 3267.5(19) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C66 H52 Cl13 N2 O6 P1 # Dc = 1.48 Fooo = 1492.00 Mu = 6.27 M = 1461.01 # Found Formula = C66 H52 Cl13 N2 O6 P1 # Dc = 1.48 FOOO = 1492.00 Mu = 6.27 M = 1461.01 _chemical_formula_sum 'C66 H52 Cl13 N2 O6 P1' _chemical_formula_moiety 'C66 H52 Cl13 N2 O6 P1' _chemical_compound_source ? _chemical_formula_weight 1461.01 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min ? _exptl_crystal_size_mid ? _exptl_crystal_size_max ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1492 _exptl_absorpt_coefficient_mu 0.627 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 1.0000 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 27915 _reflns_number_total 15362 _diffrn_reflns_av_R_equivalents 0.048 # Number of reflections with Friedels Law is 15362 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 15474 _diffrn_reflns_theta_min 1.071 _diffrn_reflns_theta_max 27.832 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.276 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min -17 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.33 _refine_diff_density_max 0.61 _refine_ls_number_reflns 7191 _refine_ls_number_restraints 0 _refine_ls_number_parameters 103 #_refine_ls_R_factor_ref 0.0509 _refine_ls_wR_factor_ref 0.0500 _refine_ls_goodness_of_fit_ref 1.1038 #_reflns_number_all 15311 _refine_ls_R_factor_all 0.1199 _refine_ls_wR_factor_all 0.1334 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7191 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_gt 0.0500 _refine_ls_shift/su_max 0.000267 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.243 0.668E-01 0.332E-02 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens P1 P 0.2499 -0.6509 -0.7637 0.0458 1.0000 Uani . . . . . . Cl2 Cl 0.2023 -0.8682 -0.5500 0.0564 1.0000 Uani . . . . . . Cl3 Cl 0.0380 -0.2813 -0.7477 0.0538 1.0000 Uani . . . . . . Cl4 Cl 0.5793 -0.7204 -0.6353 0.0598 1.0000 Uani . . . . . . Cl5 Cl 0.4707 -1.0246 -0.7576 0.0557 1.0000 Uani . . . . . . Cl6 Cl -0.0477 -0.6859 -0.8546 0.0666 1.0000 Uani . . . . . . Cl7 Cl 0.0583 -0.1105 -0.8796 0.0616 1.0000 Uani . . . . . . Cl8 Cl 0.2077 -0.0565 -0.7396 0.0578 1.0000 Uani . . . . . . Cl9 Cl 0.7090 -1.1251 -0.6710 0.0700 1.0000 Uani . . . . . . Cl1 Cl 0.1918 -0.1962 -0.9972 0.0689 1.0000 Uani . . . . . . Cl15 Cl 0.2986 -0.4528 -0.9839 0.0688 1.0000 Uani . . . . . . Cl16 Cl 0.7642 -0.9689 -0.6145 0.0711 1.0000 Uani . . . . . . Cl17 Cl 0.0314 -0.9448 -0.5821 0.0740 1.0000 Uani . . . . . . Cl14 Cl -0.0943 -0.8525 -0.7337 0.0776 1.0000 Uani . . . . . . O15 O 0.1714 -0.5234 -0.7505 0.0454 1.0000 Uani . . . . . . O16 O 0.2275 -0.7132 -0.6816 0.0432 1.0000 Uani . . . . . . O17 O 0.1351 -0.6469 -0.8018 0.0483 1.0000 Uani . . . . . . N18 N 0.2208 -0.5125 -0.5456 0.0422 1.0000 Uani . . . . . . O19 O 0.3655 -0.6598 -0.7231 0.0470 1.0000 Uani . . . . . . O20 O 0.3288 -0.7782 -0.7755 0.0478 1.0000 Uani . . . . . . N21 N 0.3253 0.0969 -1.0597 0.0422 1.0000 Uani . . . . . . O22 O 0.2694 -0.5883 -0.8453 0.0502 1.0000 Uani . . . . . . C23 C 0.5543 -0.8061 -0.6699 0.0451 1.0000 Uani . . . . . . C24 C 0.1584 -0.5103 -0.4887 0.0431 1.0000 Uani . . . . . . C25 C 0.1571 -0.3356 -0.5318 0.0463 1.0000 Uani . . . . . . C26 C 0.1859 0.2002 -1.0000 0.0463 1.0000 Uani . . . . . . C27 C 0.3804 -0.0647 -1.1043 0.0417 1.0000 Uani . . . . . . C28 C 0.1197 -0.4076 -0.4773 0.0470 1.0000 Uani . . . . . . C29 C 0.2848 0.0866 -0.9969 0.0434 1.0000 Uani . . . . . . C30 C 0.2782(3) -0.6136(3) -0.5661(2) 0.0443 1.0000 Uani . . . . . . C31 C 0.3024 -0.1694 -0.7654 0.0444 1.0000 Uani . . . . . . C32 C 0.1356(3) -0.5926(3) -0.4487(2) 0.0457 1.0000 Uani . . . . . . C33 C 0.1362 -0.8240 -0.6342 0.0469 1.0000 Uani . . . . . . C34 C 0.1567 -0.7527 -0.6877 0.0442 1.0000 Uani . . . . . . C35 C 0.1756 0.2682 -1.0761 0.0485 1.0000 Uani . . . . . . C36 C 0.4310 -0.8326 -0.7371 0.0431 1.0000 Uani . . . . . . C37 C 0.3819 -0.7037 -0.5142 0.0438 1.0000 Uani . . . . . . C38 C 0.5752 -0.4494 -0.8174 0.0552 1.0000 Uani . . . . . . C39 C 0.3421 -0.1456 -0.8300 0.0498 1.0000 Uani . . . . . . C40 C 0.2720(4) -0.0225(4) -1.1352(2) 0.0491 1.0000 Uani . . . . . . C41 C 0.2682(4) 0.2406(3) -1.1788(2) 0.0474 1.0000 Uani . . . . . . C42 C 0.2244 -0.4160 -0.5726 0.0436 1.0000 Uani . . . . . . C43 C 0.2577 0.2042 -1.1093 0.0438 1.0000 Uani . . . . . . C44 C 0.2777(3) -0.2973(4) -0.6643(2) 0.0473 1.0000 Uani . . . . . . C45 C 0.6111 -0.9859 -0.6858 0.0489 1.0000 Uani . . . . . . C46 C 0.1688 -0.4399 -0.8049 0.0458 1.0000 Uani . . . . . . C47 C 0.0984(4) 0.3775(4) -1.1144(3) 0.0578 1.0000 Uani . . . . . . C48 C 0.0015 -0.8137 -0.7167 0.0544 1.0000 Uani . . . . . . C49 C 0.4527 -0.7651 -0.7089 0.0450 1.0000 Uani . . . . . . C50 C 0.2847(3) -0.3998(3) -0.6272(2) 0.0446 1.0000 Uani . . . . . . C51 C 0.4154(3) 0.0067(3) -1.0785(2) 0.0441 1.0000 Uani . . . . . . C52 C 0.2245 -0.4763 -0.8586 0.0476 1.0000 Uani . . . . . . C53 C 0.4585(4) -0.1722(4) -1.1009(2) 0.0525 1.0000 Uani . . . . . . C54 C 0.0302(4) -0.4661(4) -0.3841(2) 0.0531 1.0000 Uani . . . . . . C55 C 0.3294(3) -0.0149(3) -0.9444(2) 0.0460 1.0000 Uani . . . . . . C56 C 0.4121(3) -0.3762(3) -0.7464(2) 0.0488 1.0000 Uani . . . . . . C57 C 0.2441(4) -0.0884(4) -1.1618(2) 0.0564 1.0000 Uani . . . . . . C58 C 0.1238 -0.2513 -0.8713 0.0464 1.0000 Uani . . . . . . C59 C 0.4284(4) -0.8119(4) -0.5158(3) 0.0549 1.0000 Uani . . . . . . C60 C 0.6345 -0.9178 -0.6600 0.0506 1.0000 Uani . . . . . . C61 C 0.1029 -0.7138 -0.7559 0.0469 1.0000 Uani . . . . . . C62 C 0.1818 -0.2892 -0.9236 0.0508 1.0000 Uani . . . . . . C63 C 0.0804(3) 0.1882(4) -0.9868(2) 0.0524 1.0000 Uani . . . . . . C64 C 0.0237 -0.7414 -0.7707 0.0506 1.0000 Uani . . . . . . C65 C 0.0565(4) -0.3851(4) -0.4246(2) 0.0533 1.0000 Uani . . . . . . C66 C 0.1896(4) 0.3500(4) -1.2172(2) 0.0561 1.0000 Uani . . . . . . C67 C 0.1080(4) 0.4159(4) -1.1854(3) 0.0586 1.0000 Uani . . . . . . C68 C 0.3299 -0.2781 -0.7229 0.0447 1.0000 Uani . . . . . . C69 C 0.2310 -0.4027 -0.9184 0.0495 1.0000 Uani . . . . . . C70 C 0.0530(4) -0.2299(3) -0.5770(2) 0.0558 1.0000 Uani . . . . . . C71 C 0.5069 -0.9429 -0.7250 0.0458 1.0000 Uani . . . . . . C72 C 0.2111(4) 0.2505(4) -0.9486(2) 0.0552 1.0000 Uani . . . . . . C73 C 0.1158 -0.3278 -0.8113 0.0464 1.0000 Uani . . . . . . C74 C 0.2990(3) -0.0382(3) -0.8771(2) 0.0453 1.0000 Uani . . . . . . C75 C 0.0578 -0.8550 -0.6487 0.0540 1.0000 Uani . . . . . . C76 C 0.3241(4) -0.1957(4) -1.1579(3) 0.0592 1.0000 Uani . . . . . . C77 C 0.0691(3) -0.5674(4) -0.3965(2) 0.0523 1.0000 Uani . . . . . . C78 C 0.6301(4) -0.4102(4) -0.8795(3) 0.0650 1.0000 Uani . . . . . . C79 C 0.4890(4) -0.3496(4) -0.7953(3) 0.0619 1.0000 Uani . . . . . . C80 C 0.4318(4) -0.6809(4) -0.4664(2) 0.0577 1.0000 Uani . . . . . . C81 C 0.4307(4) -0.2368(4) -1.1274(3) 0.0635 1.0000 Uani . . . . . . C82 C 0.2323(4) -0.3049(4) -0.4953(2) 0.0600 1.0000 Uani . . . . . . C83 C 0.5273(4) -0.7662(4) -0.4206(3) 0.0670 1.0000 Uani . . . . . . C84 C 0.4262(4) -0.2437(4) -0.8529(3) 0.0693 1.0000 Uani . . . . . . C85 C 0.6678(4) -0.5300(5) -0.7554(3) 0.0730 1.0000 Uani . . . . . . C86 C 0.5736(4) -0.8732(4) -0.4236(3) 0.0653 1.0000 Uani . . . . . . C87 C 0.5238(4) -0.8962(4) -0.4716(3) 0.0717 1.0000 Uani . . . . . . C88 C 0.5223(4) -0.5116(4) -0.8395(3) 0.0740 1.0000 Uani . . . . . . H301 H 0.2996 -0.5949 -0.6138 0.0529 1.0000 Uiso R . . . . . H302 H 0.2261 -0.6440 -0.5688 0.0531 1.0000 Uiso R . . . . . H321 H 0.1639 -0.6643 -0.4571 0.0555 1.0000 Uiso R . . . . . H401 H 0.2161 0.0533 -1.1383 0.0625 1.0000 Uiso R . . . . . H411 H 0.3266 0.1920 -1.2005 0.0575 1.0000 Uiso R . . . . . H441 H 0.2314 -0.2336 -0.6481 0.0592 1.0000 Uiso R . . . . . H471 H 0.0398 0.4255 -1.0928 0.0686 1.0000 Uiso R . . . . . H501 H 0.3349 -0.4642 -0.6413 0.0565 1.0000 Uiso R . . . . . H511 H 0.4489 0.0402 -1.1166 0.0571 1.0000 Uiso R . . . . . H512 H 0.4738 -0.0416 -1.0368 0.0573 1.0000 Uiso R . . . . . H531 H 0.5332 -0.2021 -1.0792 0.0667 1.0000 Uiso R . . . . . H541 H -0.0150 -0.4516 -0.3474 0.0607 1.0000 Uiso R . . . . . H551 H 0.3883 -0.0786 -0.9553 0.0562 1.0000 Uiso R . . . . . H561 H 0.3696 -0.4005 -0.7700 0.0628 1.0000 Uiso R . . . . . H562 H 0.4588 -0.4402 -0.7035 0.0621 1.0000 Uiso R . . . . . H571 H 0.1678 -0.0592 -1.1823 0.0712 1.0000 Uiso R . . . . . H591 H 0.3928 -0.8285 -0.5485 0.0655 1.0000 Uiso R . . . . . H631 H 0.0146 0.2612 -0.9981 0.0800 1.0000 Uiso R . . . . . H632 H 0.0716 0.1473 -1.0164 0.0799 1.0000 Uiso R . . . . . H633 H 0.0859 0.1458 -0.9375 0.0797 1.0000 Uiso R . . . . . H651 H 0.0296 -0.3141 -0.4153 0.0606 1.0000 Uiso R . . . . . H661 H 0.1933 0.3792 -1.2669 0.0695 1.0000 Uiso R . . . . . H671 H 0.0553 0.4918 -1.2131 0.0692 1.0000 Uiso R . . . . . H701 H 0.0748 -0.1824 -0.6124 0.0739 1.0000 Uiso R . . . . . H702 H 0.0062 -0.2495 -0.6011 0.0742 1.0000 Uiso R . . . . . H703 H 0.0074 -0.1860 -0.5481 0.0741 1.0000 Uiso R . . . . . H721 H 0.1478 0.3227 -0.9516 0.0889 1.0000 Uiso R . . . . . H722 H 0.2767 0.2600 -0.9603 0.0888 1.0000 Uiso R . . . . . H723 H 0.2274 0.2003 -0.9005 0.0889 1.0000 Uiso R . . . . . H741 H 0.2440 0.0247 -0.8632 0.0575 1.0000 Uiso R . . . . . H761 H 0.3040 -0.2412 -1.1770 0.0744 1.0000 Uiso R . . . . . H771 H 0.0494 -0.6222 -0.3681 0.0607 1.0000 Uiso R . . . . . H781 H 0.6923 -0.4738 -0.8882 0.0980 1.0000 Uiso R . . . . . H782 H 0.5747 -0.3668 -0.9226 0.0978 1.0000 Uiso R . . . . . H783 H 0.6571 -0.3608 -0.8699 0.0981 1.0000 Uiso R . . . . . H791 H 0.5332 -0.3290 -0.7666 0.0756 1.0000 Uiso R . . . . . H801 H 0.4000 -0.6046 -0.4648 0.0736 1.0000 Uiso R . . . . . H811 H 0.4868 -0.3116 -1.1243 0.0773 1.0000 Uiso R . . . . . H821 H 0.2565 -0.2600 -0.5298 0.0998 1.0000 Uiso R . . . . . H822 H 0.2974 -0.3735 -0.4664 0.1000 1.0000 Uiso R . . . . . H823 H 0.1901 -0.2615 -0.4645 0.0999 1.0000 Uiso R . . . . . H831 H 0.5593 -0.7487 -0.3861 0.0785 1.0000 Uiso R . . . . . H841 H 0.3840 -0.2585 -0.8866 0.0782 1.0000 Uiso R . . . . . H842 H 0.4800 -0.2224 -0.8785 0.0773 1.0000 Uiso R . . . . . H851 H 0.6376 -0.5536 -0.7124 0.1009 1.0000 Uiso R . . . . . H852 H 0.7213 -0.5971 -0.7664 0.1012 1.0000 Uiso R . . . . . H853 H 0.7076 -0.4923 -0.7448 0.1010 1.0000 Uiso R . . . . . H861 H 0.6418 -0.9328 -0.3923 0.0756 1.0000 Uiso R . . . . . H871 H 0.5560 -0.9725 -0.4728 0.0815 1.0000 Uiso R . . . . . H881 H 0.4986 -0.5505 -0.7985 0.1270 1.0000 Uiso R . . . . . H882 H 0.5752 -0.5672 -0.8591 0.1268 1.0000 Uiso R . . . . . H883 H 0.4565 -0.4603 -0.8752 0.1270 1.0000 Uiso R . . . . . 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 P1 0.0419 0.0512 0.0453 -0.0217 0.0090 -0.0196 Cl2 0.0508 0.0517 0.0548 -0.0098 0.0044 -0.0192 Cl3 0.0559 0.0539 0.0551 -0.0242 0.0156 -0.0255 Cl4 0.0617 0.0719 0.0584 -0.0206 0.0043 -0.0419 Cl5 0.0606 0.0542 0.0584 -0.0259 0.0179 -0.0281 Cl6 0.0491 0.0931 0.0645 -0.0441 0.0057 -0.0289 Cl7 0.0644 0.0536 0.0659 -0.0133 0.0045 -0.0308 Cl8 0.0747 0.0452 0.0516 -0.0209 0.0189 -0.0245 Cl9 0.0623 0.0516 0.0703 -0.0118 0.0011 -0.0110 Cl1 0.0697 0.0766 0.0553 -0.0053 0.0103 -0.0401 Cl15 0.0681 0.0876 0.0464 -0.0242 0.0195 -0.0326 Cl16 0.0509 0.0790 0.0651 -0.0072 -0.0083 -0.0254 Cl17 0.0773 0.0624 0.0943 -0.0235 0.0198 -0.0441 Cl14 0.0630 0.0847 0.1115 -0.0512 0.0138 -0.0451 O15 0.0480 0.0464 0.0389 -0.0156 0.0108 -0.0194 O16 0.0405 0.0517 0.0402 -0.0192 0.0086 -0.0217 O17 0.0426 0.0561 0.0447 -0.0229 0.0076 -0.0187 N18 0.0433 0.0401 0.0406 -0.0152 0.0087 -0.0167 O19 0.0408 0.0504 0.0509 -0.0209 0.0072 -0.0201 O20 0.0376 0.0539 0.0502 -0.0242 0.0049 -0.0161 N21 0.0440 0.0374 0.0444 -0.0162 0.0056 -0.0171 O22 0.0491 0.0567 0.0401 -0.0197 0.0113 -0.0194 C23 0.0470 0.0550 0.0437 -0.0180 0.0127 -0.0316 C24 0.0420 0.0426 0.0385 -0.0132 0.0024 -0.0150 C25 0.0509 0.0411 0.0482 -0.0201 0.0106 -0.0200 C26 0.0424 0.0469 0.0528 -0.0261 0.0066 -0.0182 C27 0.0442 0.0439 0.0401 -0.0158 0.0098 -0.0224 C28 0.0508 0.0393 0.0447 -0.0133 0.0005 -0.0168 C29 0.0438 0.0456 0.0470 -0.0183 0.0053 -0.0244 C30 0.0522 0.0395 0.0478 -0.0219 0.0115 -0.0228 C31 0.0431 0.0408 0.0498 -0.0176 0.0050 -0.0187 C32 0.0506 0.0469 0.0391 -0.0104 0.0015 -0.0248 C33 0.0466 0.0392 0.0534 -0.0189 0.0091 -0.0171 C34 0.0353 0.0445 0.0537 -0.0260 0.0084 -0.0140 C35 0.0446 0.0466 0.0573 -0.0178 0.0002 -0.0233 C36 0.0412 0.0477 0.0452 -0.0211 0.0106 -0.0218 C37 0.0421 0.0438 0.0448 -0.0187 0.0106 -0.0176 C38 0.0570 0.0490 0.0654 -0.0246 0.0211 -0.0268 C39 0.0437 0.0452 0.0650 -0.0196 0.0156 -0.0241 C40 0.0528 0.0440 0.0517 -0.0173 0.0038 -0.0230 C41 0.0506 0.0453 0.0464 -0.0145 0.0074 -0.0231 C42 0.0428 0.0403 0.0458 -0.0132 0.0032 -0.0186 C43 0.0419 0.0372 0.0521 -0.0154 -0.0017 -0.0179 C44 0.0465 0.0480 0.0484 -0.0185 0.0064 -0.0218 C45 0.0461 0.0471 0.0445 -0.0094 0.0089 -0.0183 C46 0.0340 0.0575 0.0421 -0.0152 0.0029 -0.0192 C47 0.0427 0.0501 0.0781 -0.0274 0.0041 -0.0162 C48 0.0457 0.0563 0.0789 -0.0421 0.0164 -0.0271 C49 0.0404 0.0495 0.0447 -0.0152 0.0132 -0.0214 C50 0.0425 0.0435 0.0513 -0.0182 0.0094 -0.0215 C51 0.0448 0.0453 0.0452 -0.0184 0.0093 -0.0217 C52 0.0413 0.0534 0.0453 -0.0187 0.0039 -0.0187 C53 0.0424 0.0484 0.0691 -0.0272 0.0070 -0.0189 C54 0.0467 0.0618 0.0408 -0.0146 0.0134 -0.0192 C55 0.0428 0.0446 0.0513 -0.0178 0.0112 -0.0204 C56 0.0466 0.0490 0.0541 -0.0177 0.0141 -0.0249 C57 0.0527 0.0544 0.0684 -0.0245 -0.0012 -0.0274 C58 0.0395 0.0542 0.0460 -0.0146 0.0024 -0.0234 C59 0.0488 0.0495 0.0681 -0.0237 0.0037 -0.0221 C60 0.0425 0.0630 0.0415 -0.0105 0.0094 -0.0251 C61 0.0417 0.0499 0.0521 -0.0301 0.0116 -0.0168 C62 0.0445 0.0608 0.0445 -0.0097 0.0058 -0.0271 C63 0.0396 0.0601 0.0573 -0.0194 0.0058 -0.0233 C64 0.0375 0.0569 0.0603 -0.0348 0.0050 -0.0156 C65 0.0497 0.0524 0.0479 -0.0229 0.0058 -0.0128 C66 0.0551 0.0517 0.0554 -0.0106 -0.0062 -0.0240 C67 0.0551 0.0477 0.0628 -0.0052 -0.0058 -0.0233 C68 0.0457 0.0496 0.0421 -0.0162 0.0039 -0.0244 C69 0.0387 0.0665 0.0403 -0.0167 0.0064 -0.0230 C70 0.0596 0.0416 0.0574 -0.0186 0.0105 -0.0157 C71 0.0489 0.0507 0.0420 -0.0190 0.0145 -0.0252 C72 0.0520 0.0561 0.0634 -0.0314 0.0038 -0.0234 C73 0.0407 0.0580 0.0437 -0.0189 0.0072 -0.0246 C74 0.0406 0.0449 0.0540 -0.0194 0.0076 -0.0214 C75 0.0510 0.0465 0.0705 -0.0267 0.0188 -0.0238 C76 0.0649 0.0523 0.0716 -0.0281 0.0050 -0.0320 C77 0.0477 0.0576 0.0421 -0.0046 0.0063 -0.0243 C78 0.0796 0.0584 0.0634 -0.0312 0.0307 -0.0320 C79 0.0776 0.0469 0.0624 -0.0216 0.0235 -0.0289 C80 0.0559 0.0569 0.0613 -0.0304 0.0028 -0.0210 C81 0.0512 0.0458 0.0933 -0.0326 0.0038 -0.0170 C82 0.0746 0.0593 0.0581 -0.0267 0.0128 -0.0372 C83 0.0510 0.0807 0.0664 -0.0330 -0.0066 -0.0234 C84 0.0678 0.0534 0.0760 -0.0168 0.0270 -0.0234 C85 0.0621 0.0794 0.0753 -0.0162 0.0138 -0.0373 C86 0.0473 0.0590 0.0674 -0.0133 0.0002 -0.0116 C87 0.0516 0.0475 0.0999 -0.0211 -0.0060 -0.0119 C88 0.0592 0.0712 0.1150 -0.0606 0.0255 -0.0327 _refine_ls_extinction_method None _oxford_refine_ls_scale 0.16782(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 . O15 . 1.7196(5) yes P1 . O16 . 1.7277(4) yes P1 . O17 . 1.7264(5) yes P1 . O19 . 1.7239(5) yes P1 . O20 . 1.7071(5) yes P1 . O22 . 1.7042(4) yes Cl2 . C33 . 1.7236(4) yes Cl3 . C73 . 1.7245(3) yes Cl4 . C23 . 1.7213(4) yes Cl5 . C71 . 1.7311(4) yes Cl6 . C64 . 1.7259(4) yes Cl7 . C58 . 1.7262(6) yes Cl8 . C31 . 1.7422(4) yes Cl9 . C45 . 1.7321(5) yes Cl1 . C62 . 1.7275(4) yes Cl15 . C69 . 1.7220(3) yes Cl16 . C60 . 1.7252(6) yes Cl17 . C75 . 1.7252(4) yes Cl14 . C48 . 1.7130(5) yes O15 . C46 . 1.3474(3) yes O16 . C34 . 1.3488(4) yes O17 . C61 . 1.3486(3) yes N18 . C24 . 1.4103(3) yes N18 . C30 . 1.460(4) yes N18 . C42 . 1.3459(4) yes O19 . C49 . 1.3581(4) yes O20 . C36 . 1.3526(4) yes N21 . C29 . 1.3628(3) yes N21 . C43 . 1.4187(4) yes N21 . C51 . 1.446(4) yes O22 . C52 . 1.3544(5) yes C23 . C49 . 1.3777(4) yes C23 . C60 . 1.4022(4) yes C24 . C28 . 1.3898(5) yes C24 . C32 . 1.379(4) yes C25 . C28 . 1.5265(3) yes C25 . C42 . 1.5331(3) yes C25 . C70 . 1.540(4) yes C25 . C82 . 1.550(4) yes C26 . C29 . 1.5329(4) yes C26 . C35 . 1.5217(3) yes C26 . C63 . 1.538(4) yes C26 . C72 . 1.535(4) yes C27 . C40 . 1.388(4) yes C27 . C51 . 1.512(4) yes C27 . C53 . 1.379(4) yes C28 . C65 . 1.368(4) yes C29 . C55 . 1.375(4) yes C30 . C37 . 1.524(4) yes C30 . H301 . 0.992 no C30 . H302 . 0.999 no C31 . C39 . 1.4072(3) yes C31 . C68 . 1.4022(5) yes C32 . C77 . 1.389(6) yes C32 . H321 . 0.972 no C33 . C34 . 1.3732(3) yes C33 . C75 . 1.3963(4) yes C34 . C61 . 1.3892(3) yes C35 . C43 . 1.3781(3) yes C35 . C47 . 1.390(4) yes C36 . C49 . 1.3832(3) yes C36 . C71 . 1.3665(4) yes C37 . C59 . 1.374(4) yes C37 . C80 . 1.375(4) yes C38 . C78 . 1.543(4) yes C38 . C79 . 1.544(4) yes C38 . C85 . 1.531(5) yes C38 . C88 . 1.526(5) yes C39 . C74 . 1.386(4) yes C39 . C84 . 1.527(5) yes C40 . C57 . 1.391(6) yes C40 . H401 . 0.971 no C41 . C43 . 1.370(4) yes C41 . C66 . 1.396(6) yes C41 . H411 . 0.975 no C42 . C50 . 1.391(4) yes C44 . C50 . 1.391(5) yes C44 . C68 . 1.390(4) yes C44 . H441 . 0.977 no C45 . C60 . 1.3738(3) yes C45 . C71 . 1.4043(4) yes C46 . C52 . 1.3890(3) yes C46 . C73 . 1.3743(5) yes C47 . C67 . 1.396(6) yes C47 . H471 . 0.972 no C48 . C64 . 1.3995(3) yes C48 . C75 . 1.3950(3) yes C50 . H501 . 0.971 no C51 . H511 . 1.001 no C51 . H512 . 0.994 no C52 . C69 . 1.3788(3) yes C53 . C81 . 1.372(6) yes C53 . H531 . 0.957 no C54 . C65 . 1.397(6) yes C54 . C77 . 1.379(6) yes C54 . H541 . 0.959 no C55 . C74 . 1.398(6) yes C55 . H551 . 0.972 no C56 . C68 . 1.526(4) yes C56 . C79 . 1.527(6) yes C56 . H561 . 0.986 no C56 . H562 . 1.001 no C57 . C76 . 1.381(6) yes C57 . H571 . 0.970 no C58 . C62 . 1.3844(3) yes C58 . C73 . 1.4122(3) yes C59 . C87 . 1.376(6) yes C59 . H591 . 0.964 no C61 . C64 . 1.3746(4) yes C62 . C69 . 1.3994(5) yes C63 . H631 . 0.969 no C63 . H632 . 0.986 no C63 . H633 . 0.982 no C65 . H651 . 0.974 no C66 . C67 . 1.369(6) yes C66 . H661 . 0.973 no C67 . H671 . 0.967 no C70 . H701 . 0.976 no C70 . H702 . 0.986 no C70 . H703 . 0.973 no C72 . H721 . 0.972 no C72 . H722 . 0.983 no C72 . H723 . 0.976 no C74 . H741 . 0.975 no C76 . C81 . 1.367(6) yes C76 . H761 . 0.975 no C77 . H771 . 0.969 no C78 . H781 . 0.971 no C78 . H782 . 0.990 no C78 . H783 . 0.993 no C79 . C84 . 1.471(6) yes C79 . H791 . 1.027 no C80 . C83 . 1.394(6) yes C80 . H801 . 0.974 no C81 . H811 . 0.963 no C82 . H821 . 0.965 no C82 . H822 . 0.981 no C82 . H823 . 0.986 no C83 . C86 . 1.367(7) yes C83 . H831 . 0.971 no C84 . H841 . 1.020 no C84 . H842 . 1.001 no C85 . H851 . 0.986 no C85 . H852 . 0.979 no C85 . H853 . 0.985 no C86 . C87 . 1.381(7) yes C86 . H861 . 0.979 no C87 . H871 . 0.970 no C88 . H881 . 0.993 no C88 . H882 . 0.967 no C88 . H883 . 0.981 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O15 . P1 . O16 . 88.08(3) yes O15 . P1 . O17 . 92.986(12) yes O16 . P1 . O17 . 90.077(13) yes O15 . P1 . O19 . 88.220(13) yes O16 . P1 . O19 . 87.974(12) yes O17 . P1 . O19 . 177.673 yes O15 . P1 . O20 . 179.144 yes O16 . P1 . O20 . 91.298(11) yes O17 . P1 . O20 . 87.60(4) yes O19 . P1 . O20 . 91.17(4) yes O15 . P1 . O22 . 91.53(3) yes O16 . P1 . O22 . 178.943 yes O17 . P1 . O22 . 88.96(3) yes O19 . P1 . O22 . 93.00(3) yes O20 . P1 . O22 . 89.10(3) yes P1 . O15 . C46 . 110.704(19) yes P1 . O16 . C34 . 110.38(2) yes P1 . O17 . C61 . 110.698(16) yes C24 . N18 . C30 . 120.72(16) yes C24 . N18 . C42 . 111.954(9) yes C30 . N18 . C42 . 127.21(16) yes P1 . O19 . C49 . 109.932(13) yes P1 . O20 . C36 . 110.75(2) yes C29 . N21 . C43 . 111.542(15) yes C29 . N21 . C51 . 125.27(16) yes C43 . N21 . C51 . 122.60(17) yes P1 . O22 . C52 . 111.14(3) yes Cl4 . C23 . C49 . 119.82(3) yes Cl4 . C23 . C60 . 122.13(3) yes C49 . C23 . C60 . 118.048(9) yes N18 . C24 . C28 . 108.860(10) yes N18 . C24 . C32 . 128.62(18) yes C28 . C24 . C32 . 122.52(18) yes C28 . C25 . C42 . 101.17(2) yes C28 . C25 . C70 . 108.85(18) yes C42 . C25 . C70 . 113.26(17) yes C28 . C25 . C82 . 110.66(18) yes C42 . C25 . C82 . 111.06(18) yes C70 . C25 . C82 . 111.4(3) yes C29 . C26 . C35 . 100.857(15) yes C29 . C26 . C63 . 109.91(17) yes C35 . C26 . C63 . 110.54(17) yes C29 . C26 . C72 . 111.83(17) yes C35 . C26 . C72 . 111.51(18) yes C63 . C26 . C72 . 111.7(2) yes C40 . C27 . C51 . 121.5(2) yes C40 . C27 . C53 . 118.6(2) yes C51 . C27 . C53 . 119.8(2) yes C25 . C28 . C24 . 109.02(3) yes C25 . C28 . C65 . 131.0(2) yes C24 . C28 . C65 . 120.0(2) yes C26 . C29 . N21 . 108.66(2) yes C26 . C29 . C55 . 130.21(17) yes N21 . C29 . C55 . 121.07(17) yes N18 . C30 . C37 . 111.9(3) yes N18 . C30 . H301 . 109.7 no C37 . C30 . H301 . 109.5 no N18 . C30 . H302 . 109.2 no C37 . C30 . H302 . 109.0 no H301 . C30 . H302 . 107.4 no Cl8 . C31 . C39 . 117.72(2) yes Cl8 . C31 . C68 . 118.47(2) yes C39 . C31 . C68 . 123.716(10) yes C24 . C32 . C77 . 116.8(4) yes C24 . C32 . H321 . 121.4 no C77 . C32 . H321 . 121.8 no Cl2 . C33 . C34 . 119.606(16) yes Cl2 . C33 . C75 . 121.253(16) yes C34 . C33 . C75 . 119.07(2) yes C33 . C34 . O16 . 125.915(17) yes C33 . C34 . C61 . 120.967(19) yes O16 . C34 . C61 . 113.118(16) yes C26 . C35 . C43 . 110.347(17) yes C26 . C35 . C47 . 130.7(2) yes C43 . C35 . C47 . 119.0(2) yes O20 . C36 . C49 . 112.948(11) yes O20 . C36 . C71 . 125.483(9) yes C49 . C36 . C71 . 121.56(3) yes C30 . C37 . C59 . 118.6(2) yes C30 . C37 . C80 . 122.8(2) yes C59 . C37 . C80 . 118.5(3) yes C78 . C38 . C79 . 111.1(2) yes C78 . C38 . C85 . 107.4(3) yes C79 . C38 . C85 . 108.6(3) yes C78 . C38 . C88 . 108.0(3) yes C79 . C38 . C88 . 112.0(3) yes C85 . C38 . C88 . 109.6(3) yes C31 . C39 . C74 . 122.76(17) yes C31 . C39 . C84 . 118.30(18) yes C74 . C39 . C84 . 118.5(3) yes C27 . C40 . C57 . 120.0(4) yes C27 . C40 . H401 . 119.7 no C57 . C40 . H401 . 120.3 no C43 . C41 . C66 . 116.5(4) yes C43 . C41 . H411 . 121.6 no C66 . C41 . H411 . 121.8 no C25 . C42 . N18 . 108.97(3) yes C25 . C42 . C50 . 128.51(17) yes N18 . C42 . C50 . 122.49(17) yes N21 . C43 . C35 . 108.311(19) yes N21 . C43 . C41 . 127.45(18) yes C35 . C43 . C41 . 124.23(18) yes C50 . C44 . C68 . 125.4(4) yes C50 . C44 . H441 . 117.0 no C68 . C44 . H441 . 117.6 no Cl9 . C45 . C60 . 120.94(2) yes Cl9 . C45 . C71 . 118.98(2) yes C60 . C45 . C71 . 120.08(3) yes O15 . C46 . C52 . 113.42(3) yes O15 . C46 . C73 . 126.39(2) yes C52 . C46 . C73 . 120.169(17) yes C35 . C47 . C67 . 117.5(4) yes C35 . C47 . H471 . 121.4 no C67 . C47 . H471 . 121.2 no Cl14 . C48 . C64 . 120.270(14) yes Cl14 . C48 . C75 . 119.610(15) yes C64 . C48 . C75 . 120.119(19) yes C36 . C49 . C23 . 120.69(3) yes C36 . C49 . O19 . 113.41(3) yes C23 . C49 . O19 . 125.903(9) yes C44 . C50 . C42 . 124.8(3) yes C44 . C50 . H501 . 117.0 no C42 . C50 . H501 . 118.2 no C27 . C51 . N21 . 114.3(3) yes C27 . C51 . H511 . 108.3 no N21 . C51 . H511 . 108.2 no C27 . C51 . H512 . 109.3 no N21 . C51 . H512 . 108.5 no H511 . C51 . H512 . 107.9 no C46 . C52 . O22 . 112.98(2) yes C46 . C52 . C69 . 121.577(18) yes O22 . C52 . C69 . 125.448(8) yes C27 . C53 . C81 . 121.2(4) yes C27 . C53 . H531 . 119.1 no C81 . C53 . H531 . 119.8 no C65 . C54 . C77 . 120.5(4) yes C65 . C54 . H541 . 120.1 no C77 . C54 . H541 . 119.5 no C29 . C55 . C74 . 127.8(4) yes C29 . C55 . H551 . 116.5 no C74 . C55 . H551 . 115.8 no C68 . C56 . C79 . 113.9(3) yes C68 . C56 . H561 . 108.6 no C79 . C56 . H561 . 109.5 no C68 . C56 . H562 . 108.4 no C79 . C56 . H562 . 108.9 no H561 . C56 . H562 . 107.3 no C40 . C57 . C76 . 120.1(4) yes C40 . C57 . H571 . 119.8 no C76 . C57 . H571 . 120.1 no Cl7 . C58 . C62 . 120.454(10) yes Cl7 . C58 . C73 . 119.551(11) yes C62 . C58 . C73 . 119.982(18) yes C37 . C59 . C87 . 121.3(4) yes C37 . C59 . H591 . 118.8 no C87 . C59 . H591 . 119.8 no Cl16 . C60 . C23 . 118.694(9) yes Cl16 . C60 . C45 . 120.215(8) yes C23 . C60 . C45 . 121.09(2) yes C34 . C61 . O17 . 112.911(17) yes C34 . C61 . C64 . 120.648(16) yes O17 . C61 . C64 . 126.415(18) yes Cl1 . C62 . C58 . 120.30(2) yes Cl1 . C62 . C69 . 119.12(3) yes C58 . C62 . C69 . 120.564(17) yes C26 . C63 . H631 . 110.7 no C26 . C63 . H632 . 109.9 no H631 . C63 . H632 . 108.6 no C26 . C63 . H633 . 110.8 no H631 . C63 . H633 . 108.9 no H632 . C63 . H633 . 107.8 no Cl6 . C64 . C48 . 121.059(17) yes Cl6 . C64 . C61 . 119.903(17) yes C48 . C64 . C61 . 119.03(2) yes C54 . C65 . C28 . 118.7(4) yes C54 . C65 . H651 . 120.2 no C28 . C65 . H651 . 121.1 no C41 . C66 . C67 . 120.5(4) yes C41 . C66 . H661 . 119.4 no C67 . C66 . H661 . 120.2 no C47 . C67 . C66 . 122.3(4) yes C47 . C67 . H671 . 119.0 no C66 . C67 . H671 . 118.6 no C56 . C68 . C31 . 117.99(16) yes C56 . C68 . C44 . 119.9(2) yes C31 . C68 . C44 . 121.88(17) yes Cl15 . C69 . C62 . 122.301(17) yes Cl15 . C69 . C52 . 119.239(19) yes C62 . C69 . C52 . 118.459(10) yes C25 . C70 . H701 . 110.4 no C25 . C70 . H702 . 111.3 no H701 . C70 . H702 . 108.7 no C25 . C70 . H703 . 110.8 no H701 . C70 . H703 . 107.7 no H702 . C70 . H703 . 107.7 no Cl5 . C71 . C45 . 122.57(3) yes Cl5 . C71 . C36 . 119.00(3) yes C45 . C71 . C36 . 118.421(9) yes C26 . C72 . H721 . 110.7 no C26 . C72 . H722 . 109.1 no H721 . C72 . H722 . 109.4 no C26 . C72 . H723 . 110.1 no H721 . C72 . H723 . 108.9 no H722 . C72 . H723 . 108.7 no Cl3 . C73 . C58 . 120.608(17) yes Cl3 . C73 . C46 . 120.238(17) yes C58 . C73 . C46 . 119.14(3) yes C55 . C74 . C39 . 123.3(3) yes C55 . C74 . H741 . 117.8 no C39 . C74 . H741 . 118.9 no Cl17 . C75 . C33 . 119.623(19) yes Cl17 . C75 . C48 . 120.285(19) yes C33 . C75 . C48 . 120.091(14) yes C57 . C76 . C81 . 119.6(4) yes C57 . C76 . H761 . 119.7 no C81 . C76 . H761 . 120.8 no C32 . C77 . C54 . 121.6(4) yes C32 . C77 . H771 . 119.2 no C54 . C77 . H771 . 119.2 no C38 . C78 . H781 . 110.8 no C38 . C78 . H782 . 109.7 no H781 . C78 . H782 . 108.4 no C38 . C78 . H783 . 111.0 no H781 . C78 . H783 . 109.1 no H782 . C78 . H783 . 107.8 no C38 . C79 . C56 . 114.3(3) yes C38 . C79 . C84 . 115.6(4) yes C56 . C79 . C84 . 111.6(4) yes C38 . C79 . H791 . 106.9 no C56 . C79 . H791 . 105.3 no C84 . C79 . H791 . 101.6 no C37 . C80 . C83 . 120.5(4) yes C37 . C80 . H801 . 119.5 no C83 . C80 . H801 . 120.0 no C53 . C81 . C76 . 120.5(4) yes C53 . C81 . H811 . 119.5 no C76 . C81 . H811 . 120.0 no C25 . C82 . H821 . 110.6 no C25 . C82 . H822 . 109.9 no H821 . C82 . H822 . 109.8 no C25 . C82 . H823 . 109.7 no H821 . C82 . H823 . 108.4 no H822 . C82 . H823 . 108.3 no C80 . C83 . C86 . 120.3(5) yes C80 . C83 . H831 . 118.9 no C86 . C83 . H831 . 120.8 no C39 . C84 . C79 . 114.9(4) yes C39 . C84 . H841 . 108.4 no C79 . C84 . H841 . 106.9 no C39 . C84 . H842 . 108.8 no C79 . C84 . H842 . 109.1 no H841 . C84 . H842 . 108.6 no C38 . C85 . H851 . 111.8 no C38 . C85 . H852 . 110.9 no H851 . C85 . H852 . 108.5 no C38 . C85 . H853 . 109.4 no H851 . C85 . H853 . 107.6 no H852 . C85 . H853 . 108.7 no C83 . C86 . C87 . 119.3(5) yes C83 . C86 . H861 . 120.5 no C87 . C86 . H861 . 120.2 no C86 . C87 . C59 . 120.0(5) yes C86 . C87 . H871 . 119.1 no C59 . C87 . H871 . 120.9 no C38 . C88 . H881 . 110.6 no C38 . C88 . H882 . 110.5 no H881 . C88 . H882 . 108.1 no C38 . C88 . H883 . 111.6 no H881 . C88 . H883 . 108.0 no H882 . C88 . H883 . 107.9 no