# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 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_calixdiquinonepyridine_macrocycle #============================================================================== # start Validation Reply Form _vrf_PLAT029_calixdiquinonepyridine_macrocycle ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.885 RESPONSE: Crystals were extremely small and poorly diffracting. Synchrotron radiation was used but despite this the data were extremely weak with many reflections missed. ; # end Validation Reply Form _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; A tertiary-butyl group attached to the upper rim of the calixdiquinone was found to be disordered by rotation about the central carbon atom. This was modelled as being split over two sites. The occupancy of the two sites were refined (0.706:0.294 for C(65),C(66), C(67) and C(165), C(166) and C(167) respectively). ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 12.6430(12) _cell_length_b 14.2835(16) _cell_length_c 16.9650(12) _cell_angle_alpha 80.423(8) _cell_angle_beta 87.747(7) _cell_angle_gamma 74.632(9) _cell_volume 2912.9(5) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' 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 0.002 0.002 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 0.004 0.003 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 0.007 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' S 0.105 0.116 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C90 H10 N1 O1 S0.50 # Dc = 1.30 Fooo = 1200.00 Mu = 0.93 M = 1137.11 # Found Formula = C65 H69 N3 O13 S1 # Dc = 1.29 FOOO = 1200.00 Mu = 1.24 M = 1132.34 _chemical_formula_sum 'C65 H69 N3 O13 S' _chemical_formula_moiety ' C63 H63 N3 O12, C2 H6 O S' _chemical_compound_source synthesised _chemical_formula_weight 1132.34 _cell_measurement_reflns_used 7985 _cell_measurement_theta_min 2 _cell_measurement_theta_max 28 _cell_measurement_temperature 100 _exptl_crystal_description plate _exptl_crystal_colour colour _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_max 0.05 _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1200.000 _exptl_absorpt_coefficient_mu 0.124 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type synchrotron _diffrn_measurement_device Area _diffrn_radiation_monochromator 'Si(1 1 1) double-crystal monochromator' _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 0 _diffrn_reflns_number 27664 _reflns_number_total 13925 _diffrn_reflns_av_R_equivalents 0.103 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 13925 # Theoretical number of reflections is about 20212 _diffrn_reflns_theta_min 1.619 _diffrn_reflns_theta_max 29.501 _diffrn_measured_fraction_theta_max 0.781 _diffrn_reflns_theta_full 25.076 _diffrn_measured_fraction_theta_full 0.885 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min -19 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 4.37 _oxford_diffrn_Wilson_scale 0.01 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.61 _refine_diff_density_max 1.23 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 9464 _refine_ls_number_restraints 0 _refine_ls_number_parameters 766 _oxford_refine_ls_R_factor_ref 0.1190 _refine_ls_wR_factor_ref 0.3129 _refine_ls_goodness_of_fit_ref 0.9922 _refine_ls_shift/su_max 0.0002667 _refine_ls_shift/su_mean 0.0000163 # The values computed with all filters except I/sigma _oxford_reflns_number_all 9466 _refine_ls_R_factor_all 0.1191 _refine_ls_wR_factor_all 0.3130 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6383 _refine_ls_R_factor_gt 0.0979 _refine_ls_wR_factor_gt 0.2492 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #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: 0.724E+04 0.122E+05 0.773E+04 0.331E+04 790. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 O1 O 0.1524(2) 0.81236(19) 0.27756(15) 0.0541 1.0000 Uani . . . . . . C2 C 0.0819(3) 0.8471(3) 0.2265(2) 0.0515 1.0000 Uani . . . . . . C3 C 0.1111(3) 0.8650(3) 0.1403(2) 0.0521 1.0000 Uani . . . . . . C4 C 0.2312(3) 0.8415(3) 0.1203(2) 0.0531 1.0000 Uani . . . . . . C5 C 0.2826(3) 0.7303(3) 0.1316(2) 0.0505 1.0000 Uani . . . . . . C6 C 0.3616(3) 0.6837(3) 0.1899(2) 0.0507 1.0000 Uani . . . . . . O7 O 0.4044(2) 0.7401(2) 0.23430(15) 0.0552 1.0000 Uani . . . . . . C8 C 0.4892(3) 0.7778(3) 0.1910(2) 0.0595 1.0000 Uani . . . . . . C9 C 0.5261(3) 0.8421(3) 0.2391(2) 0.0573 1.0000 Uani . . . . . . O10 O 0.5917(2) 0.77949(19) 0.30481(16) 0.0559 1.0000 Uani . . . . . . C11 C 0.6254(3) 0.8242(3) 0.3603(2) 0.0512 1.0000 Uani . . . . . . C12 C 0.6916(3) 0.7613(3) 0.4226(2) 0.0480 1.0000 Uani . . . . . . C13 C 0.7295(3) 0.7985(3) 0.4818(2) 0.0509 1.0000 Uani . . . . . . C14 C 0.7037(3) 0.8996(3) 0.4821(2) 0.0526 1.0000 Uani . . . . . . O15 O 0.7479(2) 0.9298(2) 0.54383(16) 0.0579 1.0000 Uani . . . . . . C16 C 0.7038(4) 1.0296(3) 0.5575(3) 0.0648 1.0000 Uani . . . . . . C17 C 0.7711(5) 1.0514(3) 0.6183(3) 0.0734 1.0000 Uani . . . . . . N18 N 0.7752(3) 0.9873(2) 0.69545(19) 0.0583 1.0000 Uani . . . . . . C19 C 0.8671(3) 0.9521(3) 0.7386(2) 0.0567 1.0000 Uani . . . . . . O20 O 0.9564(3) 0.9646(2) 0.7146(2) 0.0722 1.0000 Uani . . . . . . C21 C 0.8571(3) 0.8973(3) 0.8211(2) 0.0550 1.0000 Uani . . . . . . C22 C 0.7586(3) 0.9053(3) 0.8605(2) 0.0531 1.0000 Uani . . . . . . C23 C 0.7556(3) 0.8488(3) 0.9359(2) 0.0599 1.0000 Uani . . . . . . C24 C 0.6492(4) 0.8494(4) 0.9799(2) 0.0676 1.0000 Uani . . . . . . O25 O 0.6462(3) 0.8314(3) 1.05270(19) 0.0925 1.0000 Uani . . . . . . N26 N 0.5607(3) 0.8698(4) 0.9329(2) 0.0782 1.0000 Uani . . . . . . C27 C 0.4521(4) 0.8713(6) 0.9659(3) 0.0933 1.0000 Uani . . . . . . C28 C 0.3771(4) 0.8710(5) 0.9030(3) 0.0814 1.0000 Uani . . . . . . O29 O 0.4002(3) 0.7871(3) 0.8702(2) 0.0833 1.0000 Uani . . . . . . C30 C 0.3340(4) 0.7798(4) 0.8076(3) 0.0735 1.0000 Uani . . . . . . C31 C 0.2649(5) 0.8601(4) 0.7662(4) 0.0874 1.0000 Uani . . . . . . C32 C 0.2021(4) 0.8488(4) 0.6993(3) 0.0806 1.0000 Uani . . . . . . C33 C 0.2156(3) 0.7604(3) 0.6798(2) 0.0614 1.0000 Uani . . . . . . O34 O 0.1590(3) 0.7365(2) 0.62136(16) 0.0639 1.0000 Uani . . . . . . C35 C 0.0762(3) 0.8125(3) 0.5764(3) 0.0609 1.0000 Uani . . . . . . C36 C 0.0171(3) 0.7646(3) 0.5263(2) 0.0591 1.0000 Uani . . . . . . O37 O 0.0895(2) 0.7274(2) 0.46521(15) 0.0550 1.0000 Uani . . . . . . C38 C 0.0438(3) 0.6798(3) 0.4158(2) 0.0507 1.0000 Uani . . . . . . C39 C 0.0807(3) 0.5778(3) 0.4218(2) 0.0512 1.0000 Uani . . . . . . C40 C 0.0387(3) 0.5298(3) 0.3694(2) 0.0529 1.0000 Uani . . . . . . C41 C -0.0415(3) 0.5811(3) 0.3117(2) 0.0484 1.0000 Uani . . . . . . C42 C -0.0764(3) 0.6831(3) 0.3088(2) 0.0504 1.0000 Uani . . . . . . C43 C -0.0333(3) 0.7335(3) 0.3569(2) 0.0490 1.0000 Uani . . . . . . C44 C -0.0614(3) 0.8458(3) 0.3363(2) 0.0530 1.0000 Uani . . . . . . C45 C -0.0380(3) 0.8716(3) 0.2491(2) 0.0532 1.0000 Uani . . . . . . C46 C -0.1138(3) 0.9077(3) 0.1914(2) 0.0588 1.0000 Uani . . . . . . C47 C -0.0843(4) 0.9286(3) 0.1066(3) 0.0632 1.0000 Uani . . . . . . C48 C 0.0311(3) 0.9028(3) 0.0859(2) 0.0603 1.0000 Uani . . . . . . O49 O -0.1567(3) 0.9689(3) 0.0553(2) 0.0763 1.0000 Uani . . . . . . C50 C -0.0855(3) 0.5355(3) 0.2502(2) 0.0584 1.0000 Uani . . . . . . C51 C -0.0318(4) 0.4261(3) 0.2546(3) 0.0636 1.0000 Uani . . . . . . C52 C -0.0645(7) 0.5886(4) 0.1660(3) 0.0950 1.0000 Uani . . . . . . C53 C -0.2096(4) 0.5514(4) 0.2606(4) 0.0831 1.0000 Uani . . . . . . C54 C 0.1710(3) 0.5202(3) 0.4819(2) 0.0562 1.0000 Uani . . . . . . C55 C 0.2790(3) 0.5465(3) 0.4595(2) 0.0526 1.0000 Uani . . . . . . C56 C 0.3355(3) 0.5134(3) 0.3863(2) 0.0494 1.0000 Uani . . . . . . O57 O 0.3067(2) 0.45480(18) 0.35255(16) 0.0554 1.0000 Uani . . . . . . C58 C 0.4312(3) 0.5543(3) 0.3553(2) 0.0530 1.0000 Uani . . . . . . C59 C 0.4764(3) 0.5318(3) 0.2753(2) 0.0594 1.0000 Uani . . . . . . C60 C 0.3984(3) 0.5814(3) 0.2059(2) 0.0528 1.0000 Uani . . . . . . C61 C 0.3632(3) 0.5263(3) 0.1564(2) 0.0562 1.0000 Uani . . . . . . C62 C 0.2916(3) 0.5712(3) 0.0919(2) 0.0527 1.0000 Uani . . . . . . C63 C 0.2498(3) 0.6730(3) 0.0827(2) 0.0536 1.0000 Uani . . . . . . C64 C 0.2643(4) 0.5099(3) 0.0334(2) 0.0597 1.0000 Uani . . . . . . C65 C 0.2228(7) 0.4254(5) 0.0783(4) 0.0782 0.7062 Uani . . . 1 1 . C66 C 0.3702(7) 0.4683(7) -0.0114(5) 0.0918 0.7062 Uani . . . 1 1 . C67 C 0.1786(7) 0.5723(5) -0.0279(4) 0.0795 0.7062 Uani . . . 1 1 . C68 C 0.4721(3) 0.6059(3) 0.4001(2) 0.0587 1.0000 Uani . . . . . . C69 C 0.4236(4) 0.6290(3) 0.4771(2) 0.0629 1.0000 Uani . . . . . . C70 C 0.3227(3) 0.5985(3) 0.5013(2) 0.0570 1.0000 Uani . . . . . . O71 O 0.4644(3) 0.6724(3) 0.5185(2) 0.0880 1.0000 Uani . . . . . . C72 C 0.2914(5) 0.6802(4) 0.7241(3) 0.0801 1.0000 Uani . . . . . . C73 C 0.3525(4) 0.6910(4) 0.7858(3) 0.0764 1.0000 Uani . . . . . . C74 C 0.8545(5) 0.7906(4) 0.9690(3) 0.0776 1.0000 Uani . . . . . . N75 N 0.9510(4) 0.7824(4) 0.9325(3) 0.0848 1.0000 Uani . . . . . . C76 C 0.9522(4) 0.8348(3) 0.8598(3) 0.0695 1.0000 Uani . . . . . . C77 C 0.6388(4) 0.9625(3) 0.4219(3) 0.0666 1.0000 Uani . . . . . . C78 C 0.6013(4) 0.9253(3) 0.3603(3) 0.0630 1.0000 Uani . . . . . . O79 O 0.5853(2) 0.8829(2) 0.75281(18) 0.0640 1.0000 Uani . . . . . . S80 S 0.60236(7) 0.77783(7) 0.73916(5) 0.0513 1.0000 Uani . . . . . . C81 C 0.5401(3) 0.7837(3) 0.6459(2) 0.0514 1.0000 Uani . . . . . . C82 C 0.7429(3) 0.7379(3) 0.7099(2) 0.0569 1.0000 Uani . . . . . . C165 C 0.3306(15) 0.3974(11) 0.0459(10) 0.0744 0.2938 Uani . . . 1 2 . C166 C 0.2852(14) 0.5522(12) -0.0524(8) 0.0656 0.2938 Uani . . . 1 2 . C167 C 0.1416(16) 0.5097(15) 0.0429(10) 0.0802 0.2938 Uani . . . 1 2 . H41 H 0.2692 0.8639 0.1588 0.0644 1.0000 Uiso R . . . . . H42 H 0.2430 0.8718 0.0658 0.0641 1.0000 Uiso R . . . . . H81 H 0.4604 0.8146 0.1395 0.0711 1.0000 Uiso R . . . . . H82 H 0.5523 0.7226 0.1832 0.0708 1.0000 Uiso R . . . . . H91 H 0.5703 0.8786 0.2056 0.0691 1.0000 Uiso R . . . . . H92 H 0.4622 0.8864 0.2584 0.0690 1.0000 Uiso R . . . . . H121 H 0.7080 0.6937 0.4215 0.0580 1.0000 Uiso R . . . . . H131 H 0.7761 0.7558 0.5217 0.0611 1.0000 Uiso R . . . . . H161 H 0.7017 1.0754 0.5069 0.0788 1.0000 Uiso R . . . . . H162 H 0.6287 1.0373 0.5771 0.0777 1.0000 Uiso R . . . . . H171 H 0.7413 1.1201 0.6245 0.0875 1.0000 Uiso R . . . . . H172 H 0.8450 1.0420 0.5970 0.0880 1.0000 Uiso R . . . . . H221 H 0.6953 0.9475 0.8377 0.0637 1.0000 Uiso R . . . . . H271 H 0.4248 0.9302 0.9907 0.1116 1.0000 Uiso R . . . . . H272 H 0.4566 0.8127 1.0056 0.1121 1.0000 Uiso R . . . . . H311 H 0.2560 0.9224 0.7793 0.1052 1.0000 Uiso R . . . . . H321 H 0.1540 0.9038 0.6695 0.0971 1.0000 Uiso R . . . . . H352 H 0.0252 0.8452 0.6129 0.0731 1.0000 Uiso R . . . . . H351 H 0.1067 0.8597 0.5427 0.0732 1.0000 Uiso R . . . . . H361 H -0.0477 0.8124 0.5024 0.0709 1.0000 Uiso R . . . . . H362 H -0.0057 0.7112 0.5602 0.0704 1.0000 Uiso R . . . . . H401 H 0.0665 0.4609 0.3720 0.0627 1.0000 Uiso R . . . . . H421 H -0.1312 0.7189 0.2722 0.0599 1.0000 Uiso R . . . . . H442 H -0.0146 0.8700 0.3679 0.0640 1.0000 Uiso R . . . . . H441 H -0.1368 0.8740 0.3475 0.0639 1.0000 Uiso R . . . . . H461 H -0.1884 0.9207 0.2044 0.0708 1.0000 Uiso R . . . . . H481 H 0.0515 0.9140 0.0319 0.0725 1.0000 Uiso R . . . . . H511 H -0.0590 0.4031 0.2112 0.0944 1.0000 Uiso R . . . . . H512 H -0.0499 0.3914 0.3048 0.0944 1.0000 Uiso R . . . . . H513 H 0.0477 0.4150 0.2496 0.0944 1.0000 Uiso R . . . . . H521 H -0.0832 0.5551 0.1262 0.1416 1.0000 Uiso R . . . . . H522 H -0.1101 0.6562 0.1606 0.1421 1.0000 Uiso R . . . . . H523 H 0.0128 0.5883 0.1617 0.1419 1.0000 Uiso R . . . . . H533 H -0.2398 0.5287 0.2186 0.1247 1.0000 Uiso R . . . . . H532 H -0.2434 0.6200 0.2586 0.1249 1.0000 Uiso R . . . . . H531 H -0.2246 0.5160 0.3115 0.1248 1.0000 Uiso R . . . . . H542 H 0.1506 0.5357 0.5345 0.0671 1.0000 Uiso R . . . . . H541 H 0.1805 0.4505 0.4816 0.0667 1.0000 Uiso R . . . . . H591 H 0.5442 0.5518 0.2668 0.0709 1.0000 Uiso R . . . . . H592 H 0.4923 0.4616 0.2766 0.0712 1.0000 Uiso R . . . . . H611 H 0.3850 0.4582 0.1665 0.0669 1.0000 Uiso R . . . . . H631 H 0.1973 0.7046 0.0428 0.0634 1.0000 Uiso R . . . . . H652 H 0.1986 0.3913 0.0407 0.1169 0.7062 Uiso R . . 1 1 . H651 H 0.2811 0.3795 0.1104 0.1169 0.7062 Uiso R . . 1 1 . H653 H 0.1632 0.4496 0.1119 0.1169 0.7062 Uiso R . . 1 1 . H661 H 0.3555 0.4304 -0.0491 0.1375 0.7062 Uiso R . . 1 1 . H662 H 0.3977 0.5213 -0.0397 0.1379 0.7062 Uiso R . . 1 1 . H663 H 0.4260 0.4264 0.0252 0.1379 0.7062 Uiso R . . 1 1 . H671 H 0.1698 0.5331 -0.0674 0.1190 0.7062 Uiso R . . 1 1 . H672 H 0.2013 0.6282 -0.0549 0.1190 0.7062 Uiso R . . 1 1 . H673 H 0.1095 0.5956 -0.0027 0.1188 0.7062 Uiso R . . 1 1 . H681 H 0.5317 0.6302 0.3818 0.0693 1.0000 Uiso R . . . . . H701 H 0.2889 0.6169 0.5492 0.0683 1.0000 Uiso R . . . . . H721 H 0.2994 0.6173 0.7117 0.0967 1.0000 Uiso R . . . . . H731 H 0.4075 0.6378 0.8128 0.0919 1.0000 Uiso R . . . . . H741 H 0.8542 0.7550 1.0202 0.0930 1.0000 Uiso R . . . . . H761 H 1.0204 0.8304 0.8344 0.0823 1.0000 Uiso R . . . . . H771 H 0.6184 1.0297 0.4228 0.0800 1.0000 Uiso R . . . . . H781 H 0.5618 0.9699 0.3173 0.0760 1.0000 Uiso R . . . . . H1652 H 0.3192 0.3687 0.0008 0.1110 0.2938 Uiso R . . 1 2 . H1651 H 0.4078 0.3917 0.0510 0.1109 0.2938 Uiso R . . 1 2 . H1653 H 0.3058 0.3629 0.0936 0.1109 0.2938 Uiso R . . 1 2 . H1661 H 0.2871 0.5040 -0.0863 0.0980 0.2938 Uiso R . . 1 2 . H1663 H 0.3544 0.5691 -0.0560 0.0978 0.2938 Uiso R . . 1 2 . H1662 H 0.2271 0.6100 -0.0704 0.0979 0.2938 Uiso R . . 1 2 . H1673 H 0.1260 0.4629 0.0135 0.1200 0.2938 Uiso R . . 1 2 . H1672 H 0.0966 0.5744 0.0228 0.1200 0.2938 Uiso R . . 1 2 . H1671 H 0.1256 0.4926 0.0982 0.1200 0.2938 Uiso R . . 1 2 . H822 H 0.7558 0.6741 0.6931 0.0843 1.0000 Uiso R . . . . . H261 H 0.5698 0.8692 0.8819 0.0937 1.0000 Uiso R . . . . . H811 H 0.4629 0.8056 0.6525 0.0765 1.0000 Uiso R . . . . . H813 H 0.5635 0.8277 0.6059 0.0764 1.0000 Uiso R . . . . . H821 H 0.7589 0.7842 0.6668 0.0846 1.0000 Uiso R . . . . . H812 H 0.5591 0.7203 0.6310 0.0762 1.0000 Uiso R . . . . . H823 H 0.7902 0.7321 0.7542 0.0852 1.0000 Uiso R . . . . . H181 H 0.7170 0.9679 0.7102 0.0702 1.0000 Uiso R . . . . . H281 H 0.3027 0.8816 0.9243 0.0983 1.0000 Uiso R . . . . . H282 H 0.3788 0.9203 0.8569 0.0983 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 O1 0.0515(14) 0.0649(14) 0.0479(13) -0.0063(11) -0.0101(11) -0.0191(11) C2 0.053(2) 0.0538(18) 0.053(2) -0.0071(15) -0.0038(16) -0.0231(15) C3 0.056(2) 0.0564(19) 0.0462(18) -0.0042(14) -0.0062(16) -0.0210(15) C4 0.053(2) 0.061(2) 0.0473(18) -0.0027(15) -0.0005(15) -0.0218(16) C5 0.0501(19) 0.065(2) 0.0389(16) -0.0065(14) -0.0027(14) -0.0208(15) C6 0.0512(19) 0.067(2) 0.0398(16) -0.0104(14) -0.0011(14) -0.0236(16) O7 0.0552(15) 0.0704(15) 0.0462(13) -0.0087(11) -0.0048(11) -0.0270(12) C8 0.053(2) 0.084(3) 0.051(2) -0.0110(17) -0.0035(16) -0.0349(19) C9 0.055(2) 0.064(2) 0.053(2) -0.0034(16) -0.0125(17) -0.0188(16) O10 0.0526(14) 0.0590(14) 0.0583(15) -0.0100(11) -0.0150(12) -0.0162(11) C11 0.0480(19) 0.0596(19) 0.0511(19) -0.0132(15) -0.0087(15) -0.0194(15) C12 0.0433(17) 0.0521(17) 0.0509(18) -0.0069(14) -0.0048(14) -0.0165(14) C13 0.0448(18) 0.0604(19) 0.0459(17) -0.0013(14) -0.0045(14) -0.0147(14) C14 0.0489(19) 0.064(2) 0.0521(19) -0.0133(15) -0.0048(15) -0.0233(15) O15 0.0589(15) 0.0658(15) 0.0539(14) -0.0155(11) -0.0131(12) -0.0194(12) C16 0.085(3) 0.0495(19) 0.062(2) -0.0065(16) -0.007(2) -0.0218(18) C17 0.105(4) 0.067(2) 0.058(2) -0.0050(19) -0.007(2) -0.042(2) N18 0.066(2) 0.0646(18) 0.0532(17) -0.0118(14) -0.0033(15) -0.0309(15) C19 0.056(2) 0.060(2) 0.059(2) -0.0109(16) 0.0034(18) -0.0252(17) O20 0.0641(18) 0.0720(17) 0.084(2) -0.0067(15) 0.0099(15) -0.0299(14) C21 0.057(2) 0.0544(18) 0.059(2) -0.0074(15) -0.0054(17) -0.0247(15) C22 0.053(2) 0.061(2) 0.0514(19) -0.0108(15) -0.0071(16) -0.0242(16) C23 0.062(2) 0.077(2) 0.052(2) -0.0126(17) -0.0090(18) -0.0355(19) C24 0.075(3) 0.091(3) 0.049(2) -0.0136(19) -0.0021(19) -0.040(2) O25 0.101(3) 0.152(3) 0.0506(17) -0.0187(18) 0.0026(17) -0.077(3) N26 0.065(2) 0.140(4) 0.0491(19) -0.036(2) 0.0073(17) -0.049(2) C27 0.068(3) 0.167(6) 0.072(3) -0.059(3) 0.017(2) -0.056(3) C28 0.058(2) 0.137(4) 0.066(3) -0.051(3) 0.011(2) -0.037(3) O29 0.070(2) 0.128(3) 0.0650(18) -0.0317(18) -0.0007(15) -0.0387(19) C30 0.060(2) 0.111(4) 0.051(2) -0.023(2) 0.0030(19) -0.020(2) C31 0.090(4) 0.094(3) 0.094(4) -0.055(3) 0.012(3) -0.029(3) C32 0.062(3) 0.098(3) 0.092(3) -0.041(3) -0.014(2) -0.020(2) C33 0.059(2) 0.093(3) 0.0455(19) -0.0208(18) 0.0043(17) -0.038(2) O34 0.0738(18) 0.0733(17) 0.0536(15) -0.0107(12) -0.0165(13) -0.0322(14) C35 0.058(2) 0.071(2) 0.058(2) -0.0164(18) -0.0036(18) -0.0198(18) C36 0.054(2) 0.083(3) 0.0475(19) -0.0149(17) -0.0011(16) -0.0269(18) O37 0.0521(14) 0.0718(15) 0.0478(13) -0.0140(11) -0.0044(11) -0.0244(12) C38 0.0484(19) 0.065(2) 0.0463(18) -0.0108(15) -0.0016(15) -0.0272(15) C39 0.0496(19) 0.066(2) 0.0420(17) -0.0019(15) -0.0031(15) -0.0266(16) C40 0.056(2) 0.0577(19) 0.0487(18) -0.0013(15) -0.0036(16) -0.0254(16) C41 0.0423(17) 0.0631(19) 0.0427(17) -0.0026(14) -0.0066(14) -0.0213(14) C42 0.0434(18) 0.068(2) 0.0422(17) -0.0033(15) -0.0050(14) -0.0205(15) C43 0.0474(18) 0.0603(19) 0.0443(17) -0.0086(14) 0.0025(14) -0.0232(15) C44 0.0462(18) 0.061(2) 0.055(2) -0.0107(15) 0.0032(15) -0.0201(15) C45 0.0526(19) 0.0534(18) 0.054(2) -0.0038(15) -0.0028(16) -0.0176(15) C46 0.0469(19) 0.065(2) 0.064(2) 0.0004(17) -0.0046(17) -0.0192(16) C47 0.065(2) 0.061(2) 0.060(2) 0.0035(17) -0.0083(19) -0.0181(18) C48 0.063(2) 0.064(2) 0.051(2) 0.0028(16) -0.0039(18) -0.0161(17) O49 0.0675(18) 0.085(2) 0.0657(18) 0.0119(15) -0.0167(15) -0.0140(15) C50 0.060(2) 0.062(2) 0.056(2) -0.0035(16) -0.0214(17) -0.0212(17) C51 0.062(2) 0.066(2) 0.063(2) -0.0137(18) -0.0173(19) -0.0138(18) C52 0.160(6) 0.090(3) 0.045(2) -0.006(2) -0.025(3) -0.049(3) C53 0.060(3) 0.084(3) 0.112(4) -0.040(3) -0.030(3) -0.012(2) C54 0.053(2) 0.067(2) 0.0489(19) 0.0027(16) -0.0092(16) -0.0212(16) C55 0.053(2) 0.063(2) 0.0423(17) 0.0008(14) -0.0115(15) -0.0202(16) C56 0.0444(18) 0.0577(18) 0.0467(18) 0.0015(14) -0.0174(14) -0.0177(14) O57 0.0564(15) 0.0569(14) 0.0567(14) -0.0073(11) -0.0174(12) -0.0201(11) C58 0.0488(19) 0.065(2) 0.0443(18) 0.0014(15) -0.0161(15) -0.0182(15) C59 0.050(2) 0.072(2) 0.056(2) -0.0052(17) -0.0130(17) -0.0181(17) C60 0.0488(19) 0.066(2) 0.0447(18) -0.0057(15) -0.0065(15) -0.0184(16) C61 0.064(2) 0.065(2) 0.0428(18) -0.0070(15) -0.0076(16) -0.0228(17) C62 0.054(2) 0.066(2) 0.0431(18) -0.0096(15) -0.0090(15) -0.0230(16) C63 0.051(2) 0.067(2) 0.0426(17) -0.0032(15) -0.0082(15) -0.0165(16) C64 0.073(3) 0.069(2) 0.0436(18) -0.0111(16) -0.0118(17) -0.0278(19) C65 0.096(5) 0.074(4) 0.077(4) -0.015(3) -0.019(4) -0.041(4) C66 0.093(5) 0.118(6) 0.076(5) -0.050(4) 0.001(4) -0.027(4) C67 0.101(5) 0.078(4) 0.060(4) -0.014(3) -0.029(4) -0.020(4) C68 0.057(2) 0.076(2) 0.0494(19) -0.0003(17) -0.0130(17) -0.0323(18) C69 0.065(2) 0.085(3) 0.050(2) -0.0097(18) -0.0169(18) -0.037(2) C70 0.058(2) 0.077(2) 0.0423(18) -0.0069(16) -0.0121(16) -0.0272(18) O71 0.100(3) 0.131(3) 0.0635(19) -0.0316(19) -0.0015(17) -0.073(2) C72 0.095(4) 0.088(3) 0.068(3) 0.006(2) -0.031(3) -0.050(3) C73 0.081(3) 0.094(3) 0.061(3) -0.005(2) -0.013(2) -0.038(3) C74 0.093(4) 0.093(3) 0.055(2) -0.005(2) -0.019(2) -0.041(3) N75 0.070(2) 0.103(3) 0.075(3) 0.005(2) -0.023(2) -0.020(2) C76 0.056(2) 0.081(3) 0.073(3) -0.011(2) -0.009(2) -0.023(2) C77 0.063(2) 0.056(2) 0.080(3) -0.0124(19) -0.024(2) -0.0113(17) C78 0.066(2) 0.058(2) 0.069(2) -0.0084(17) -0.027(2) -0.0185(17) O79 0.0592(16) 0.0707(17) 0.0639(16) -0.0262(13) -0.0072(13) -0.0096(12) S80 0.0471(5) 0.0646(6) 0.0429(5) -0.0063(4) -0.0027(4) -0.0169(4) C81 0.0517(19) 0.0619(19) 0.0445(18) -0.0092(14) -0.0070(15) -0.0204(15) C82 0.056(2) 0.059(2) 0.062(2) -0.0190(16) -0.0023(17) -0.0189(16) C165 0.090(11) 0.060(8) 0.073(9) -0.015(7) -0.020(8) -0.014(7) C166 0.075(9) 0.084(9) 0.048(7) -0.006(6) -0.008(6) -0.040(8) C167 0.094(12) 0.106(12) 0.066(9) -0.028(8) 0.006(8) -0.062(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 8.3(5) 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 O1 . C2 . 1.215(4) yes C2 . C3 . 1.491(5) yes C2 . C45 . 1.511(5) yes C3 . C4 . 1.504(5) yes C3 . C48 . 1.336(5) yes C4 . C5 . 1.530(5) yes C4 . H41 . 0.967 no C4 . H42 . 0.976 no C5 . C6 . 1.388(5) yes C5 . C63 . 1.402(5) yes C6 . O7 . 1.404(4) yes C6 . C60 . 1.395(5) yes O7 . C8 . 1.447(4) yes C8 . C9 . 1.495(5) yes C8 . H81 . 0.972 no C8 . H82 . 0.984 no C9 . O10 . 1.441(4) yes C9 . H91 . 0.969 no C9 . H92 . 0.968 no O10 . C11 . 1.360(4) yes C11 . C12 . 1.407(5) yes C11 . C78 . 1.395(5) yes C12 . C13 . 1.367(5) yes C12 . H121 . 0.936 no C13 . C14 . 1.395(5) yes C13 . H131 . 0.939 no C14 . O15 . 1.384(4) yes C14 . C77 . 1.377(6) yes O15 . C16 . 1.441(5) yes C16 . C17 . 1.484(6) yes C16 . H161 . 0.985 no C16 . H162 . 0.979 no C17 . N18 . 1.462(5) yes C17 . H171 . 0.974 no C17 . H172 . 0.972 no N18 . C19 . 1.331(5) yes N18 . H181 . 0.866 no C19 . O20 . 1.232(5) yes C19 . C21 . 1.505(5) yes C21 . C22 . 1.377(5) yes C21 . C76 . 1.405(6) yes C22 . C23 . 1.399(6) yes C22 . H221 . 0.919 no C23 . C24 . 1.511(6) yes C23 . C74 . 1.386(7) yes C24 . O25 . 1.221(5) yes C24 . N26 . 1.339(6) yes N26 . C27 . 1.458(6) yes N26 . H261 . 0.871 no C27 . C28 . 1.457(7) yes C27 . H271 . 0.977 no C27 . H272 . 0.973 no C28 . O29 . 1.362(6) yes C28 . H281 . 0.977 no C28 . H282 . 0.965 no O29 . C30 . 1.411(6) yes C30 . C31 . 1.350(8) yes C30 . C73 . 1.339(7) yes C31 . C32 . 1.464(7) yes C31 . H311 . 0.929 no C32 . C33 . 1.325(7) yes C32 . H321 . 0.938 no C33 . O34 . 1.382(5) yes C33 . C72 . 1.408(7) yes O34 . C35 . 1.429(5) yes C35 . C36 . 1.504(5) yes C35 . H352 . 0.960 no C35 . H351 . 0.961 no C36 . O37 . 1.430(5) yes C36 . H361 . 0.970 no C36 . H362 . 0.975 no O37 . C38 . 1.390(4) yes C38 . C39 . 1.394(5) yes C38 . C43 . 1.402(5) yes C39 . C40 . 1.406(5) yes C39 . C54 . 1.528(5) yes C40 . C41 . 1.403(5) yes C40 . H401 . 0.947 no C41 . C42 . 1.398(5) yes C41 . C50 . 1.512(5) yes C42 . C43 . 1.385(5) yes C42 . H421 . 0.931 no C43 . C44 . 1.531(5) yes C44 . C45 . 1.501(5) yes C44 . H442 . 0.976 no C44 . H441 . 0.956 no C45 . C46 . 1.338(5) yes C46 . C47 . 1.473(6) yes C46 . H461 . 0.937 no C47 . C48 . 1.451(6) yes C47 . O49 . 1.243(5) yes C48 . H481 . 0.941 no C50 . C51 . 1.521(6) yes C50 . C52 . 1.551(6) yes C50 . C53 . 1.532(7) yes C51 . H511 . 0.964 no C51 . H512 . 0.964 no C51 . H513 . 0.977 no C52 . H521 . 0.960 no C52 . H522 . 0.975 no C52 . H523 . 0.976 no C53 . H533 . 0.960 no C53 . H532 . 0.955 no C53 . H531 . 0.964 no C54 . C55 . 1.528(5) yes C54 . H542 . 0.964 no C54 . H541 . 0.971 no C55 . C56 . 1.491(5) yes C55 . C70 . 1.335(5) yes C56 . O57 . 1.225(4) yes C56 . C58 . 1.519(5) yes C58 . C59 . 1.503(6) yes C58 . C68 . 1.344(5) yes C59 . C60 . 1.517(5) yes C59 . H591 . 0.972 no C59 . H592 . 0.966 no C60 . C61 . 1.399(5) yes C61 . C62 . 1.401(5) yes C61 . H611 . 0.927 no C62 . C63 . 1.393(5) yes C62 . C64 . 1.533(5) yes C63 . H631 . 0.936 no C64 . C65 . 1.520(8) yes C64 . C66 . 1.540(9) yes C64 . C67 . 1.523(8) yes C64 . C165 . 1.586(15) yes C64 . C166 . 1.521(14) yes C64 . C167 . 1.555(18) yes C65 . H652 . 0.966 no C65 . H651 . 0.963 no C65 . H653 . 0.952 no C66 . H661 . 0.957 no C66 . H662 . 0.964 no C66 . H663 . 0.964 no C67 . H671 . 0.968 no C67 . H672 . 0.958 no C67 . H673 . 0.960 no C68 . C69 . 1.471(6) yes C68 . H681 . 0.931 no C69 . C70 . 1.476(6) yes C69 . O71 . 1.220(5) yes C70 . H701 . 0.947 no C72 . C73 . 1.378(7) yes C72 . H721 . 0.934 no C73 . H731 . 0.949 no C74 . N75 . 1.332(7) yes C74 . H741 . 0.931 no N75 . C76 . 1.334(6) yes C76 . H761 . 0.940 no C77 . C78 . 1.399(6) yes C77 . H771 . 0.928 no C78 . H781 . 0.944 no O79 . S80 . 1.515(3) yes S80 . C81 . 1.774(3) yes S80 . C82 . 1.793(4) yes C81 . H811 . 0.951 no C81 . H813 . 0.941 no C81 . H812 . 0.947 no C82 . H822 . 0.971 no C82 . H821 . 0.955 no C82 . H823 . 0.957 no C165 . H1652 . 0.959 no C165 . H1651 . 0.963 no C165 . H1653 . 0.962 no C166 . H1661 . 0.963 no C166 . H1663 . 0.964 no C166 . H1662 . 0.962 no C167 . H1673 . 0.962 no C167 . H1672 . 0.962 no C167 . H1671 . 0.957 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 O1 . C2 . C3 . 121.0(3) yes O1 . C2 . C45 . 120.4(3) yes C3 . C2 . C45 . 118.6(3) yes C2 . C3 . C4 . 117.0(3) yes C2 . C3 . C48 . 119.2(3) yes C4 . C3 . C48 . 123.8(3) yes C3 . C4 . C5 . 111.4(3) yes C3 . C4 . H41 . 108.6 no C5 . C4 . H41 . 104.1 no C3 . C4 . H42 . 111.0 no C5 . C4 . H42 . 110.4 no H41 . C4 . H42 . 111.2 no C4 . C5 . C6 . 121.5(3) yes C4 . C5 . C63 . 120.1(3) yes C6 . C5 . C63 . 118.4(3) yes C5 . C6 . O7 . 119.7(3) yes C5 . C6 . C60 . 120.9(3) yes O7 . C6 . C60 . 119.3(3) yes C6 . O7 . C8 . 111.7(3) yes O7 . C8 . C9 . 109.0(3) yes O7 . C8 . H81 . 109.2 no C9 . C8 . H81 . 110.7 no O7 . C8 . H82 . 109.5 no C9 . C8 . H82 . 108.6 no H81 . C8 . H82 . 109.8 no C8 . C9 . O10 . 107.9(3) yes C8 . C9 . H91 . 108.8 no O10 . C9 . H91 . 109.6 no C8 . C9 . H92 . 108.8 no O10 . C9 . H92 . 110.9 no H91 . C9 . H92 . 110.8 no C9 . O10 . C11 . 117.3(3) yes O10 . C11 . C12 . 116.0(3) yes O10 . C11 . C78 . 126.1(3) yes C12 . C11 . C78 . 117.9(3) yes C11 . C12 . C13 . 120.9(3) yes C11 . C12 . H121 . 117.0 no C13 . C12 . H121 . 122.1 no C12 . C13 . C14 . 121.1(3) yes C12 . C13 . H131 . 119.8 no C14 . C13 . H131 . 119.0 no C13 . C14 . O15 . 116.6(3) yes C13 . C14 . C77 . 119.1(3) yes O15 . C14 . C77 . 124.3(3) yes C14 . O15 . C16 . 118.1(3) yes O15 . C16 . C17 . 109.9(4) yes O15 . C16 . H161 . 109.8 no C17 . C16 . H161 . 110.9 no O15 . C16 . H162 . 108.8 no C17 . C16 . H162 . 109.1 no H161 . C16 . H162 . 108.2 no C16 . C17 . N18 . 113.5(3) yes C16 . C17 . H171 . 107.9 no N18 . C17 . H171 . 110.5 no C16 . C17 . H172 . 106.5 no N18 . C17 . H172 . 108.8 no H171 . C17 . H172 . 109.6 no C17 . N18 . C19 . 121.9(4) yes C17 . N18 . H181 . 117.3 no C19 . N18 . H181 . 120.5 no N18 . C19 . O20 . 123.2(4) yes N18 . C19 . C21 . 116.5(3) yes O20 . C19 . C21 . 120.2(4) yes C19 . C21 . C22 . 122.9(4) yes C19 . C21 . C76 . 118.8(4) yes C22 . C21 . C76 . 118.3(4) yes C21 . C22 . C23 . 119.4(4) yes C21 . C22 . H221 . 120.5 no C23 . C22 . H221 . 120.1 no C22 . C23 . C24 . 122.0(4) yes C22 . C23 . C74 . 117.4(4) yes C24 . C23 . C74 . 120.6(4) yes C23 . C24 . O25 . 121.5(4) yes C23 . C24 . N26 . 114.9(4) yes O25 . C24 . N26 . 123.6(4) yes C24 . N26 . C27 . 121.7(4) yes C24 . N26 . H261 . 118.9 no C27 . N26 . H261 . 117.9 no N26 . C27 . C28 . 110.2(4) yes N26 . C27 . H271 . 109.2 no C28 . C27 . H271 . 110.0 no N26 . C27 . H272 . 109.5 no C28 . C27 . H272 . 107.9 no H271 . C27 . H272 . 110.0 no C27 . C28 . O29 . 115.2(5) yes C27 . C28 . H281 . 109.2 no O29 . C28 . H281 . 107.9 no C27 . C28 . H282 . 112.5 no O29 . C28 . H282 . 102.0 no H281 . C28 . H282 . 109.8 no C28 . O29 . C30 . 119.8(4) yes O29 . C30 . C31 . 121.6(5) yes O29 . C30 . C73 . 116.3(5) yes C31 . C30 . C73 . 121.7(5) yes C30 . C31 . C32 . 119.2(5) yes C30 . C31 . H311 . 121.5 no C32 . C31 . H311 . 119.3 no C31 . C32 . C33 . 119.4(5) yes C31 . C32 . H321 . 120.5 no C33 . C32 . H321 . 120.0 no C32 . C33 . O34 . 126.6(4) yes C32 . C33 . C72 . 118.4(4) yes O34 . C33 . C72 . 115.0(4) yes C33 . O34 . C35 . 118.8(3) yes O34 . C35 . C36 . 107.7(3) yes O34 . C35 . H352 . 108.7 no C36 . C35 . H352 . 109.2 no O34 . C35 . H351 . 111.9 no C36 . C35 . H351 . 110.0 no H352 . C35 . H351 . 109.3 no C35 . C36 . O37 . 108.8(3) yes C35 . C36 . H361 . 109.7 no O37 . C36 . H361 . 110.0 no C35 . C36 . H362 . 109.4 no O37 . C36 . H362 . 110.4 no H361 . C36 . H362 . 108.6 no C36 . O37 . C38 . 113.8(3) yes O37 . C38 . C39 . 119.3(3) yes O37 . C38 . C43 . 120.8(3) yes C39 . C38 . C43 . 119.7(3) yes C38 . C39 . C40 . 119.6(3) yes C38 . C39 . C54 . 119.7(3) yes C40 . C39 . C54 . 120.6(3) yes C39 . C40 . C41 . 122.0(3) yes C39 . C40 . H401 . 119.3 no C41 . C40 . H401 . 118.7 no C40 . C41 . C42 . 116.1(3) yes C40 . C41 . C50 . 124.9(3) yes C42 . C41 . C50 . 118.8(3) yes C41 . C42 . C43 . 123.5(3) yes C41 . C42 . H421 . 118.0 no C43 . C42 . H421 . 118.5 no C38 . C43 . C42 . 119.0(3) yes C38 . C43 . C44 . 122.6(3) yes C42 . C43 . C44 . 118.0(3) yes C43 . C44 . C45 . 107.6(3) yes C43 . C44 . H442 . 108.9 no C45 . C44 . H442 . 109.3 no C43 . C44 . H441 . 110.6 no C45 . C44 . H441 . 110.6 no H442 . C44 . H441 . 109.8 no C2 . C45 . C44 . 115.6(3) yes C2 . C45 . C46 . 119.0(3) yes C44 . C45 . C46 . 125.3(3) yes C45 . C46 . C47 . 122.1(4) yes C45 . C46 . H461 . 119.9 no C47 . C46 . H461 . 118.0 no C46 . C47 . C48 . 118.0(3) yes C46 . C47 . O49 . 120.4(4) yes C48 . C47 . O49 . 121.6(4) yes C47 . C48 . C3 . 123.0(4) yes C47 . C48 . H481 . 119.2 no C3 . C48 . H481 . 117.8 no C41 . C50 . C51 . 113.3(3) yes C41 . C50 . C52 . 108.2(3) yes C51 . C50 . C52 . 108.3(4) yes C41 . C50 . C53 . 109.7(3) yes C51 . C50 . C53 . 109.0(3) yes C52 . C50 . C53 . 108.1(4) yes C50 . C51 . H511 . 108.9 no C50 . C51 . H512 . 109.2 no H511 . C51 . H512 . 109.5 no C50 . C51 . H513 . 109.6 no H511 . C51 . H513 . 109.2 no H512 . C51 . H513 . 110.4 no C50 . C52 . H521 . 109.3 no C50 . C52 . H522 . 107.4 no H521 . C52 . H522 . 111.0 no C50 . C52 . H523 . 109.0 no H521 . C52 . H523 . 110.1 no H522 . C52 . H523 . 110.0 no C50 . C53 . H533 . 110.5 no C50 . C53 . H532 . 109.1 no H533 . C53 . H532 . 108.6 no C50 . C53 . H531 . 109.6 no H533 . C53 . H531 . 109.4 no H532 . C53 . H531 . 109.5 no C39 . C54 . C55 . 110.8(3) yes C39 . C54 . H542 . 109.9 no C55 . C54 . H542 . 108.1 no C39 . C54 . H541 . 108.1 no C55 . C54 . H541 . 109.5 no H542 . C54 . H541 . 110.4 no C54 . C55 . C56 . 117.3(3) yes C54 . C55 . C70 . 123.2(4) yes C56 . C55 . C70 . 119.5(3) yes C55 . C56 . O57 . 121.5(3) yes C55 . C56 . C58 . 117.6(3) yes O57 . C56 . C58 . 120.9(3) yes C56 . C58 . C59 . 116.6(3) yes C56 . C58 . C68 . 119.6(3) yes C59 . C58 . C68 . 123.8(3) yes C58 . C59 . C60 . 114.0(3) yes C58 . C59 . H591 . 108.2 no C60 . C59 . H591 . 109.6 no C58 . C59 . H592 . 108.2 no C60 . C59 . H592 . 107.7 no H591 . C59 . H592 . 108.9 no C59 . C60 . C6 . 120.0(3) yes C59 . C60 . C61 . 121.2(3) yes C6 . C60 . C61 . 118.8(3) yes C60 . C61 . C62 . 121.8(4) yes C60 . C61 . H611 . 120.4 no C62 . C61 . H611 . 117.7 no C61 . C62 . C63 . 117.2(3) yes C61 . C62 . C64 . 120.5(3) yes C63 . C62 . C64 . 122.3(3) yes C5 . C63 . C62 . 122.4(3) yes C5 . C63 . H631 . 118.4 no C62 . C63 . H631 . 119.2 no C62 . C64 . C65 . 110.4(4) yes C62 . C64 . C66 . 107.9(4) yes C65 . C64 . C66 . 109.4(6) yes C62 . C64 . C67 . 111.5(4) yes C65 . C64 . C67 . 109.3(5) yes C66 . C64 . C67 . 108.3(5) yes C62 . C64 . C165 . 115.8(6) yes C62 . C64 . C166 . 110.8(6) yes C165 . C64 . C166 . 106.2(10) yes C62 . C64 . C167 . 108.9(7) yes C165 . C64 . C167 . 105.4(11) yes C166 . C64 . C167 . 109.4(9) yes C64 . C65 . H652 . 109.9 no C64 . C65 . H651 . 109.6 no H652 . C65 . H651 . 108.5 no C64 . C65 . H653 . 110.2 no H652 . C65 . H653 . 109.2 no H651 . C65 . H653 . 109.3 no C64 . C66 . H661 . 109.8 no C64 . C66 . H662 . 110.1 no H661 . C66 . H662 . 108.8 no C64 . C66 . H663 . 110.9 no H661 . C66 . H663 . 108.4 no H662 . C66 . H663 . 108.7 no C64 . C67 . H671 . 109.1 no C64 . C67 . H672 . 110.7 no H671 . C67 . H672 . 108.3 no C64 . C67 . H673 . 110.8 no H671 . C67 . H673 . 109.6 no H672 . C67 . H673 . 108.3 no C58 . C68 . C69 . 122.1(3) yes C58 . C68 . H681 . 120.0 no C69 . C68 . H681 . 117.8 no C68 . C69 . C70 . 117.1(3) yes C68 . C69 . O71 . 121.3(4) yes C70 . C69 . O71 . 121.6(4) yes C69 . C70 . C55 . 123.2(4) yes C69 . C70 . H701 . 117.1 no C55 . C70 . H701 . 119.7 no C33 . C72 . C73 . 122.3(5) yes C33 . C72 . H721 . 118.7 no C73 . C72 . H721 . 119.0 no C72 . C73 . C30 . 118.7(5) yes C72 . C73 . H731 . 122.0 no C30 . C73 . H731 . 119.3 no C23 . C74 . N75 . 124.2(4) yes C23 . C74 . H741 . 118.4 no N75 . C74 . H741 . 117.4 no C74 . N75 . C76 . 117.6(4) yes C21 . C76 . N75 . 122.9(4) yes C21 . C76 . H761 . 119.2 no N75 . C76 . H761 . 117.9 no C14 . C77 . C78 . 120.3(4) yes C14 . C77 . H771 . 119.9 no C78 . C77 . H771 . 119.9 no C77 . C78 . C11 . 120.8(4) yes C77 . C78 . H781 . 118.8 no C11 . C78 . H781 . 120.3 no O79 . S80 . C81 . 106.76(17) yes O79 . S80 . C82 . 105.81(17) yes C81 . S80 . C82 . 98.22(18) yes S80 . C81 . H811 . 107.5 no S80 . C81 . H813 . 111.0 no H811 . C81 . H813 . 109.7 no S80 . C81 . H812 . 109.4 no H811 . C81 . H812 . 110.2 no H813 . C81 . H812 . 109.0 no S80 . C82 . H822 . 109.3 no S80 . C82 . H821 . 110.0 no H822 . C82 . H821 . 109.4 no S80 . C82 . H823 . 109.9 no H822 . C82 . H823 . 108.8 no H821 . C82 . H823 . 109.3 no C64 . C165 . H1652 . 109.6 no C64 . C165 . H1651 . 109.8 no H1652 . C165 . H1651 . 109.1 no C64 . C165 . H1653 . 109.7 no H1652 . C165 . H1653 . 109.4 no H1651 . C165 . H1653 . 109.3 no C64 . C166 . H1661 . 109.4 no C64 . C166 . H1663 . 110.2 no H1661 . C166 . H1663 . 109.0 no C64 . C166 . H1662 . 109.9 no H1661 . C166 . H1662 . 108.8 no H1663 . C166 . H1662 . 109.5 no C64 . C167 . H1673 . 110.0 no C64 . C167 . H1672 . 109.1 no H1673 . C167 . H1672 . 109.4 no C64 . C167 . H1671 . 109.7 no H1673 . C167 . H1671 . 109.3 no H1672 . C167 . H1671 . 109.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C32 . H321 . O20 1_455 120.49(16) 0.938 2.550 3.132(7) yes C35 . H352 . O20 1_455 155.95(11) 0.960 2.591 3.490(7) yes C68 . H681 . O10 . 145.16(11) 0.931 2.585 3.391(7) yes C70 . H701 . O34 . 150.66(11) 0.947 2.483 3.341(7) yes C78 . H781 . O79 2_676 157.76(12) 0.944 2.561 3.454(7) yes C82 . H822 . O57 2_666 152.32(11) 0.971 2.431 3.321(7) yes N26 . H261 . O79 . 174.38(16) 0.871 2.171 3.039(7) yes C81 . H812 . O71 . 124.24(13) 0.947 2.567 3.198(7) yes N18 . H181 . O79 . 168.05(11) 0.866 2.335 3.188(7) yes C28 . H281 . O49 2_576 133.60(15) 0.977 2.489 3.241(7) yes _iucr_refine_instruction_details_constraints ; # # Punched on 17/09/13 at 15:12:12 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 4,X'S) H ( 41,X'S) H ( 42,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) RIDE C ( 17,X'S) H ( 171,X'S) H ( 172,X'S) RIDE N ( 18,X'S) H ( 181,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE N ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 272,X'S) RIDE C ( 28,X'S) H ( 281,X'S) H ( 282,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 32,X'S) H ( 321,X'S) RIDE C ( 35,X'S) H ( 352,X'S) H ( 351,X'S) RIDE C ( 36,X'S) H ( 361,X'S) H ( 362,X'S) RIDE C ( 40,X'S) H ( 401,X'S) RIDE C ( 42,X'S) H ( 421,X'S) RIDE C ( 44,X'S) H ( 442,X'S) H ( 441,X'S) RIDE C ( 46,X'S) H ( 461,X'S) RIDE C ( 48,X'S) H ( 481,X'S) RIDE C ( 51,X'S) H ( 511,X'S) H ( 512,X'S) H ( 513,X'S) RIDE C ( 52,X'S) H ( 521,X'S) H ( 522,X'S) H ( 523,X'S) RIDE C ( 53,X'S) H ( 533,X'S) H ( 532,X'S) H ( 531,X'S) RIDE C ( 54,X'S) H ( 542,X'S) H ( 541,X'S) RIDE C ( 59,X'S) H ( 591,X'S) H ( 592,X'S) RIDE C ( 61,X'S) H ( 611,X'S) RIDE C ( 63,X'S) H ( 631,X'S) RIDE C ( 65,X'S) H ( 652,X'S) H ( 651,X'S) H ( 653,X'S) RIDE C ( 66,X'S) H ( 661,X'S) H ( 662,X'S) H ( 663,X'S) RIDE C ( 67,X'S) H ( 671,X'S) H ( 672,X'S) H ( 673,X'S) RIDE C ( 68,X'S) H ( 681,X'S) RIDE C ( 70,X'S) H ( 701,X'S) RIDE C ( 72,X'S) H ( 721,X'S) RIDE C ( 73,X'S) H ( 731,X'S) RIDE C ( 74,X'S) H ( 741,X'S) RIDE C ( 76,X'S) H ( 761,X'S) RIDE C ( 77,X'S) H ( 771,X'S) RIDE C ( 78,X'S) H ( 781,X'S) RIDE C ( 81,X'S) H ( 811,X'S) H ( 813,X'S) H ( 812,X'S) RIDE C ( 82,X'S) H ( 822,X'S) H ( 821,X'S) H ( 823,X'S) RIDE C ( 165,X'S) H (1652,X'S) H (1651,X'S) H (1653,X'S) RIDE C ( 166,X'S) H (1661,X'S) H (1663,X'S) H (1662,X'S) RIDE C ( 167,X'S) H (1673,X'S) H (1672,X'S) H (1671,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 17/09/13 at 15:12:12 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 6 1 7 x . 9 0 8 x . 6 1 5 x . 10 1 6 x . 1 -8 7 x . _database_code_depnum_ccdc_archive 'CCDC 970552'