# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1Cl2 _database_code_depnum_ccdc_archive 'CCDC 885861' #TrackingRef 'White_Beer.cif' #============================================================================== _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 ; ? ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 9.3945(5) _cell_length_b 17.0675(10) _cell_length_c 18.9451(12) _cell_angle_alpha 109.827(3) _cell_angle_beta 96.627(3) _cell_angle_gamma 93.298(2) _cell_volume 2823.3(3) _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 0.0033 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' 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 = C65 Cl1 N4 O7 # Dc = 1.16 Fooo = 1160.00 Mu = 1.23 M = 984.19 # Found Formula = C58 H80 Cl1 N9 O9 # Dc = 1.27 FOOO = 1160.00 Mu = 1.32 M = 1082.78 _chemical_formula_sum 'C58 H80 Cl1 N9 O9' _chemical_formula_moiety 'C36 H46 N2 O9, C22 H34 N7, Cl' _chemical_compound_source synthesized _chemical_formula_weight 1082.78 _cell_measurement_reflns_used 8412 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.020 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_max 0.320 _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.132 # Sheldrick geometric approximatio 0.99 1.00 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 23720 _reflns_number_total 11935 _diffrn_reflns_av_R_equivalents 0.111 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 11935 # Theoretical number of reflections is about 14470 _diffrn_reflns_theta_min 5.104 _diffrn_reflns_theta_max 27.595 _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 25.112 _diffrn_measured_fraction_theta_full 0.957 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -22 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 2.15 _oxford_diffrn_Wilson_scale 8.15 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.56 _refine_diff_density_max 0.42 # 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 7022 _refine_ls_number_restraints 0 _refine_ls_number_parameters 694 _oxford_refine_ls_R_factor_ref 0.0994 _refine_ls_wR_factor_ref 0.1832 _refine_ls_goodness_of_fit_ref 0.9711 _refine_ls_shift/su_max 0.0001713 _refine_ls_shift/su_mean 0.0000153 # The values computed from all data _oxford_reflns_number_all 7027 _refine_ls_R_factor_all 0.0996 _refine_ls_wR_factor_all 0.1836 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5232 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_gt 0.1598 # 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 # 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: 22.0 31.1 16.8 4.86 ; # Insert your own references if required - in alphabetical order 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cl1 Cl 0.31618(12) 0.15673(7) 0.78001(6) 0.0448 1.0000 Uani . . . . . . . O2 O 0.2138(3) 0.42205(18) 0.40397(16) 0.0463 1.0000 Uani . . . . . . . C3 C 0.1554(5) 0.4811(3) 0.3730(2) 0.0447 1.0000 Uani . . . . . . . C4 C 0.1236(5) 0.5555(3) 0.4372(3) 0.0447 1.0000 Uani . . . . . . . O5 O 0.2535(3) 0.59128(17) 0.48779(16) 0.0411 1.0000 Uani . . . . . . . C6 C 0.2417(5) 0.6723(3) 0.5417(3) 0.0451 1.0000 Uani . . . . . . . C7 C 0.1400(5) 0.6724(3) 0.5975(3) 0.0487 1.0000 Uani . . . . . . . O8 O 0.1910(4) 0.62993(19) 0.64743(16) 0.0515 1.0000 Uani . . . . . . . C9 C 0.2269(5) 0.6843(3) 0.7244(2) 0.0460 1.0000 Uani . . . . . . . C10 C 0.2555(5) 0.6337(3) 0.7741(3) 0.0459 1.0000 Uani . . . . . . . O11 O 0.3922(3) 0.60181(19) 0.76300(17) 0.0460 1.0000 Uani . . . . . . . C12 C 0.4316(5) 0.5482(3) 0.8004(2) 0.0374 1.0000 Uani . . . . . . . C13 C 0.5636(5) 0.5173(3) 0.7873(2) 0.0420 1.0000 Uani . . . . . . . C14 C 0.6116(5) 0.4599(3) 0.8179(3) 0.0448 1.0000 Uani . . . . . . . C15 C 0.5317(5) 0.4333(3) 0.8637(2) 0.0398 1.0000 Uani . . . . . . . O16 O 0.5891(3) 0.37525(19) 0.89196(18) 0.0476 1.0000 Uani . . . . . . . C17 C 0.5118(5) 0.3466(3) 0.9399(2) 0.0430 1.0000 Uani . . . . . . . C18 C 0.6029(5) 0.2924(3) 0.9702(3) 0.0448 1.0000 Uani . . . . . . . N19 N 0.6044(4) 0.2089(2) 0.9145(2) 0.0448 1.0000 Uani . . . . . . . C20 C 0.6847(5) 0.1547(3) 0.9358(3) 0.0479 1.0000 Uani . . . . . . . O21 O 0.7739(4) 0.1793(2) 0.9940(2) 0.0585 1.0000 Uani . . . . . . . C22 C 0.6538(5) 0.0629(3) 0.8889(3) 0.0427 1.0000 Uani . . . . . . . C23 C 0.5702(5) 0.0328(3) 0.8172(2) 0.0400 1.0000 Uani . . . . . . . C24 C 0.5328(5) -0.0528(3) 0.7819(2) 0.0397 1.0000 Uani . . . . . . . C25 C 0.5799(5) -0.1076(3) 0.8179(3) 0.0417 1.0000 Uani . . . . . . . C26 C 0.6621(5) -0.0797(3) 0.8893(3) 0.0415 1.0000 Uani . . . . . . . C27 C 0.6991(5) 0.0068(3) 0.9233(3) 0.0416 1.0000 Uani . . . . . . . C28 C 0.7028(5) -0.1374(3) 0.9329(3) 0.0484 1.0000 Uani . . . . . . . C29 C 0.8658(6) -0.1309(4) 0.9535(4) 0.0764 1.0000 Uani . . . . . . . C30 C 0.6323(6) -0.1115(3) 1.0049(3) 0.0600 1.0000 Uani . . . . . . . C31 C 0.6443(7) -0.2283(3) 0.8875(3) 0.0713 1.0000 Uani . . . . . . . C32 C 0.4369(5) -0.0904(3) 0.7075(3) 0.0434 1.0000 Uani . . . . . . . O33 O 0.4272(3) -0.16631(19) 0.67113(17) 0.0489 1.0000 Uani . . . . . . . N34 N 0.3605(4) -0.0388(2) 0.6822(2) 0.0436 1.0000 Uani . . . . . . . C35 C 0.2553(5) -0.0714(3) 0.6131(3) 0.0464 1.0000 Uani . . . . . . . C36 C 0.2004(5) -0.0011(3) 0.5907(3) 0.0450 1.0000 Uani . . . . . . . O37 O 0.3138(3) 0.03645(19) 0.56610(17) 0.0446 1.0000 Uani . . . . . . . C38 C 0.2814(5) 0.0975(3) 0.5358(2) 0.0406 1.0000 Uani . . . . . . . C39 C 0.3839(5) 0.1184(3) 0.4968(2) 0.0422 1.0000 Uani . . . . . . . C40 C 0.3612(5) 0.1766(3) 0.4615(2) 0.0404 1.0000 Uani . . . . . . . C41 C 0.2327(5) 0.2141(3) 0.4657(2) 0.0410 1.0000 Uani . . . . . . . O42 O 0.1982(3) 0.2711(2) 0.43129(18) 0.0501 1.0000 Uani . . . . . . . C43 C 0.2946(5) 0.2885(3) 0.3853(3) 0.0494 1.0000 Uani . . . . . . . C44 C 0.2290(5) 0.3452(3) 0.3479(3) 0.0491 1.0000 Uani . . . . . . . C45 C 0.1322(5) 0.1945(3) 0.5064(2) 0.0425 1.0000 Uani . . . . . . . C46 C 0.1542(5) 0.1357(3) 0.5413(2) 0.0414 1.0000 Uani . . . . . . . C47 C 0.4009(5) 0.4650(3) 0.8784(2) 0.0428 1.0000 Uani . . . . . . . C48 C 0.3532(5) 0.5232(3) 0.8469(2) 0.0425 1.0000 Uani . . . . . . . N49 N 0.4060(4) 0.4152(2) 0.60955(19) 0.0367 1.0000 Uani . . . . . . . C50 C 0.4255(5) 0.4788(3) 0.5737(3) 0.0476 1.0000 Uani . . . . . . . C51 C 0.2879(5) 0.4118(3) 0.6421(2) 0.0386 1.0000 Uani . . . . . . . C52 C 0.2669(5) 0.3550(3) 0.6784(2) 0.0384 1.0000 Uani . . . . . . . C53 C 0.1390(4) 0.3533(3) 0.7155(2) 0.0374 1.0000 Uani . . . . . . . N54 N 0.0454(4) 0.4130(2) 0.7240(2) 0.0432 1.0000 Uani . . . . . . . N55 N -0.0541(4) 0.3971(2) 0.7624(2) 0.0473 1.0000 Uani . . . . . . . N56 N -0.0220(4) 0.3281(2) 0.77863(19) 0.0387 1.0000 Uani . . . . . . . C57 C 0.0970(5) 0.3000(3) 0.7506(2) 0.0408 1.0000 Uani . . . . . . . C58 C -0.1086(5) 0.2960(3) 0.8237(3) 0.0455 1.0000 Uani . . . . . . . C59 C -0.0227(5) 0.2965(3) 0.8969(3) 0.0507 1.0000 Uani . . . . . . . C60 C 0.0279(6) 0.3862(3) 0.9510(3) 0.0598 1.0000 Uani . . . . . . . C61 C 0.1049(6) 0.3915(3) 1.0277(3) 0.0573 1.0000 Uani . . . . . . . C62 C 0.0112(5) 0.3634(3) 1.0758(3) 0.0555 1.0000 Uani . . . . . . . C63 C 0.0796(5) 0.3781(3) 1.1552(3) 0.0577 1.0000 Uani . . . . . . . C64 C 0.3720(4) 0.3012(3) 0.6795(2) 0.0384 1.0000 Uani . . . . . . . C65 C 0.4922(4) 0.3035(3) 0.6441(2) 0.0365 1.0000 Uani . . . . . . . C66 C 0.5068(5) 0.3621(3) 0.6091(2) 0.0388 1.0000 Uani . . . . . . . C67 C 0.6010(4) 0.2443(3) 0.6423(2) 0.0377 1.0000 Uani . . . . . . . N68 N 0.7198(4) 0.2451(2) 0.6071(2) 0.0484 1.0000 Uani . . . . . . . N69 N 0.7884(4) 0.1802(2) 0.6076(2) 0.0506 1.0000 Uani . . . . . . . N70 N 0.7143(4) 0.1384(2) 0.6425(2) 0.0427 1.0000 Uani . . . . . . . C71 C 0.5963(5) 0.1766(3) 0.6648(2) 0.0405 1.0000 Uani . . . . . . . C72 C 0.7563(5) 0.0591(3) 0.6469(3) 0.0515 1.0000 Uani . . . . . . . C73 C 0.8644(5) 0.0665(3) 0.7158(3) 0.0461 1.0000 Uani . . . . . . . C74 C 0.8990(5) -0.0201(3) 0.7146(3) 0.0463 1.0000 Uani . . . . . . . C75 C 1.0094(5) -0.0174(3) 0.7803(3) 0.0493 1.0000 Uani . . . . . . . C76 C 1.0458(6) -0.1030(3) 0.7798(3) 0.0574 1.0000 Uani . . . . . . . C77 C 1.1611(6) -0.0992(3) 0.8442(3) 0.0636 1.0000 Uani . . . . . . . H31 H 0.2201 0.4977 0.3429 0.0539 1.0000 Uiso R . . . . . . H32 H 0.0609 0.4548 0.3418 0.0520 1.0000 Uiso R . . . . . . H41 H 0.0867 0.5979 0.4178 0.0521 1.0000 Uiso R . . . . . . H42 H 0.0488 0.5393 0.4624 0.0521 1.0000 Uiso R . . . . . . H61 H 0.3372 0.7000 0.5687 0.0542 1.0000 Uiso R . . . . . . H62 H 0.2073 0.7097 0.5125 0.0544 1.0000 Uiso R . . . . . . H71 H 0.1283 0.7311 0.6269 0.0591 1.0000 Uiso R . . . . . . H72 H 0.0436 0.6435 0.5709 0.0596 1.0000 Uiso R . . . . . . H91 H 0.1497 0.7187 0.7423 0.0569 1.0000 Uiso R . . . . . . H92 H 0.3151 0.7198 0.7301 0.0581 1.0000 Uiso R . . . . . . H101 H 0.2505 0.6689 0.8282 0.0567 1.0000 Uiso R . . . . . . H102 H 0.1760 0.5892 0.7600 0.0559 1.0000 Uiso R . . . . . . H131 H 0.6238 0.5374 0.7565 0.0496 1.0000 Uiso R . . . . . . H141 H 0.7028 0.4393 0.8090 0.0517 1.0000 Uiso R . . . . . . H171 H 0.4854 0.3943 0.9815 0.0482 1.0000 Uiso R . . . . . . H172 H 0.4218 0.3148 0.9098 0.0472 1.0000 Uiso R . . . . . . H181 H 0.5661 0.2872 1.0165 0.0504 1.0000 Uiso R . . . . . . H182 H 0.6999 0.3200 0.9816 0.0509 1.0000 Uiso R . . . . . . H231 H 0.5377 0.0705 0.7942 0.0528 1.0000 Uiso R . . . . . . H251 H 0.5548 -0.1654 0.7916 0.0535 1.0000 Uiso R . . . . . . H271 H 0.7566 0.0282 0.9719 0.0502 1.0000 Uiso R . . . . . . H293 H 0.8872 -0.1682 0.9819 0.1113 1.0000 Uiso R . . . . . . H292 H 0.9058 -0.0754 0.9842 0.1108 1.0000 Uiso R . . . . . . H291 H 0.9102 -0.1493 0.9075 0.1107 1.0000 Uiso R . . . . . . H301 H 0.6485 -0.1505 1.0312 0.0881 1.0000 Uiso R . . . . . . H302 H 0.6781 -0.0567 1.0406 0.0885 1.0000 Uiso R . . . . . . H303 H 0.5323 -0.1080 0.9940 0.0879 1.0000 Uiso R . . . . . . H311 H 0.6707 -0.2652 0.9150 0.1024 1.0000 Uiso R . . . . . . H312 H 0.5371 -0.2326 0.8772 0.1021 1.0000 Uiso R . . . . . . H313 H 0.6806 -0.2462 0.8383 0.1015 1.0000 Uiso R . . . . . . H351 H 0.1717 -0.1071 0.6204 0.0575 1.0000 Uiso R . . . . . . H352 H 0.3061 -0.1082 0.5730 0.0563 1.0000 Uiso R . . . . . . H361 H 0.1627 0.0410 0.6347 0.0586 1.0000 Uiso R . . . . . . H362 H 0.1203 -0.0235 0.5499 0.0584 1.0000 Uiso R . . . . . . H391 H 0.4743 0.0888 0.4933 0.0447 1.0000 Uiso R . . . . . . H401 H 0.4347 0.1926 0.4346 0.0518 1.0000 Uiso R . . . . . . H431 H 0.3916 0.3161 0.4142 0.0586 1.0000 Uiso R . . . . . . H432 H 0.3104 0.2353 0.3466 0.0573 1.0000 Uiso R . . . . . . H441 H 0.2928 0.3541 0.3098 0.0546 1.0000 Uiso R . . . . . . H442 H 0.1322 0.3191 0.3197 0.0554 1.0000 Uiso R . . . . . . H451 H 0.0452 0.2207 0.5120 0.0464 1.0000 Uiso R . . . . . . H461 H 0.0829 0.1219 0.5696 0.0538 1.0000 Uiso R . . . . . . H471 H 0.3431 0.4463 0.9094 0.0494 1.0000 Uiso R . . . . . . H481 H 0.2650 0.5455 0.8590 0.0486 1.0000 Uiso R . . . . . . H501 H 0.4096 0.5334 0.6068 0.0712 1.0000 Uiso R . . . . . . H502 H 0.5242 0.4822 0.5604 0.0704 1.0000 Uiso R . . . . . . H503 H 0.3565 0.4656 0.5272 0.0701 1.0000 Uiso R . . . . . . H511 H 0.2184 0.4505 0.6399 0.0491 1.0000 Uiso R . . . . . . H571 H 0.1417 0.2552 0.7542 0.0468 1.0000 Uiso R . . . . . . H581 H -0.1901 0.3275 0.8366 0.0526 1.0000 Uiso R . . . . . . H582 H -0.1476 0.2370 0.7944 0.0536 1.0000 Uiso R . . . . . . H591 H -0.0784 0.2660 0.9234 0.0565 1.0000 Uiso R . . . . . . H592 H 0.0617 0.2689 0.8825 0.0561 1.0000 Uiso R . . . . . . H601 H -0.0571 0.4184 0.9601 0.0688 1.0000 Uiso R . . . . . . H602 H 0.0903 0.4138 0.9259 0.0692 1.0000 Uiso R . . . . . . H611 H 0.1433 0.4499 1.0556 0.0686 1.0000 Uiso R . . . . . . H612 H 0.1854 0.3579 1.0199 0.0691 1.0000 Uiso R . . . . . . H621 H -0.0744 0.3921 1.0756 0.0649 1.0000 Uiso R . . . . . . H622 H -0.0191 0.3031 1.0491 0.0648 1.0000 Uiso R . . . . . . H631 H 0.0183 0.3559 1.1813 0.0805 1.0000 Uiso R . . . . . . H632 H 0.1046 0.4366 1.1851 0.0820 1.0000 Uiso R . . . . . . H633 H 0.1675 0.3515 1.1546 0.0806 1.0000 Uiso R . . . . . . H641 H 0.3599 0.2635 0.7058 0.0417 1.0000 Uiso R . . . . . . H661 H 0.5885 0.3669 0.5845 0.0502 1.0000 Uiso R . . . . . . H711 H 0.5297 0.1594 0.6903 0.0513 1.0000 Uiso R . . . . . . H721 H 0.6666 0.0274 0.6496 0.0614 1.0000 Uiso R . . . . . . H722 H 0.7968 0.0288 0.6005 0.0617 1.0000 Uiso R . . . . . . H731 H 0.8247 0.0952 0.7637 0.0534 1.0000 Uiso R . . . . . . H732 H 0.9525 0.0988 0.7158 0.0522 1.0000 Uiso R . . . . . . H741 H 0.8053 -0.0536 0.7121 0.0549 1.0000 Uiso R . . . . . . H742 H 0.9391 -0.0458 0.6688 0.0558 1.0000 Uiso R . . . . . . H751 H 0.9720 0.0083 0.8291 0.0581 1.0000 Uiso R . . . . . . H752 H 1.0962 0.0155 0.7801 0.0565 1.0000 Uiso R . . . . . . H761 H 0.9575 -0.1365 0.7798 0.0698 1.0000 Uiso R . . . . . . H762 H 1.0826 -0.1338 0.7322 0.0699 1.0000 Uiso R . . . . . . H771 H 1.1682 -0.1563 0.8449 0.0937 1.0000 Uiso R . . . . . . H772 H 1.1280 -0.0660 0.8925 0.0939 1.0000 Uiso R . . . . . . H773 H 1.2505 -0.0747 0.8392 0.0945 1.0000 Uiso R . . . . . . H191 H 0.5517 0.1933 0.8672 0.0557 1.0000 Uiso R . . . . . . H341 H 0.3738 0.0174 0.7088 0.0541 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 Cl1 0.0446(6) 0.0374(6) 0.0497(7) 0.0138(5) -0.0024(5) 0.0090(5) O2 0.0560(19) 0.0375(17) 0.0409(18) 0.0096(15) -0.0008(15) 0.0097(14) C3 0.052(3) 0.040(3) 0.040(3) 0.015(2) -0.005(2) 0.003(2) C4 0.039(3) 0.047(3) 0.049(3) 0.018(2) 0.000(2) 0.006(2) O5 0.0372(16) 0.0395(17) 0.0408(17) 0.0074(14) 0.0003(13) 0.0091(13) C6 0.051(3) 0.035(2) 0.047(3) 0.012(2) 0.005(2) 0.007(2) C7 0.062(3) 0.042(3) 0.043(3) 0.013(2) 0.007(2) 0.019(2) O8 0.072(2) 0.0434(18) 0.0363(18) 0.0097(15) 0.0024(16) 0.0187(16) C9 0.050(3) 0.042(3) 0.042(3) 0.010(2) 0.002(2) 0.011(2) C10 0.046(3) 0.042(3) 0.046(3) 0.012(2) 0.003(2) 0.010(2) O11 0.0427(18) 0.0511(19) 0.0490(18) 0.0231(16) 0.0042(14) 0.0123(15) C12 0.040(3) 0.032(2) 0.034(2) 0.008(2) -0.003(2) 0.0000(19) C13 0.043(3) 0.039(3) 0.042(3) 0.013(2) 0.004(2) 0.006(2) C14 0.037(2) 0.050(3) 0.045(3) 0.013(2) 0.003(2) 0.007(2) C15 0.042(3) 0.037(2) 0.037(2) 0.011(2) -0.003(2) 0.004(2) O16 0.0445(18) 0.0499(19) 0.057(2) 0.0273(16) 0.0101(15) 0.0140(15) C17 0.046(3) 0.041(3) 0.039(3) 0.010(2) 0.005(2) 0.005(2) C18 0.049(3) 0.036(2) 0.045(3) 0.012(2) -0.003(2) 0.003(2) N19 0.052(2) 0.041(2) 0.038(2) 0.0124(18) -0.0029(18) 0.0056(18) C20 0.046(3) 0.045(3) 0.055(3) 0.022(2) -0.001(2) 0.009(2) O21 0.057(2) 0.047(2) 0.063(2) 0.0207(17) -0.0224(19) -0.0041(16) C22 0.036(2) 0.041(3) 0.051(3) 0.016(2) 0.004(2) 0.006(2) C23 0.039(2) 0.044(3) 0.041(3) 0.018(2) 0.006(2) 0.012(2) C24 0.040(2) 0.039(3) 0.040(3) 0.012(2) 0.006(2) 0.009(2) C25 0.046(3) 0.034(2) 0.045(3) 0.012(2) 0.008(2) 0.007(2) C26 0.041(3) 0.038(3) 0.045(3) 0.011(2) 0.009(2) 0.008(2) C27 0.037(2) 0.047(3) 0.045(3) 0.021(2) 0.005(2) 0.007(2) C28 0.055(3) 0.047(3) 0.047(3) 0.019(2) 0.007(2) 0.012(2) C29 0.058(3) 0.089(4) 0.110(5) 0.069(4) 0.008(3) 0.022(3) C30 0.074(4) 0.055(3) 0.056(3) 0.025(3) 0.012(3) 0.008(3) C31 0.106(5) 0.045(3) 0.063(3) 0.023(3) -0.004(3) 0.019(3) C32 0.046(3) 0.039(3) 0.046(3) 0.016(2) 0.008(2) 0.011(2) O33 0.058(2) 0.0356(19) 0.0477(19) 0.0084(15) 0.0017(15) 0.0097(15) N34 0.048(2) 0.037(2) 0.039(2) 0.0084(17) -0.0082(17) 0.0043(17) C35 0.049(3) 0.044(3) 0.045(3) 0.015(2) 0.001(2) 0.003(2) C36 0.045(3) 0.044(3) 0.041(3) 0.013(2) -0.005(2) -0.002(2) O37 0.0418(17) 0.0459(18) 0.0493(18) 0.0218(15) 0.0029(14) 0.0037(14) C38 0.041(3) 0.037(2) 0.038(2) 0.009(2) -0.002(2) 0.002(2) C39 0.043(3) 0.039(3) 0.037(2) 0.007(2) -0.004(2) 0.003(2) C40 0.043(3) 0.037(2) 0.034(2) 0.006(2) -0.0014(19) 0.004(2) C41 0.042(3) 0.036(2) 0.038(2) 0.008(2) -0.005(2) 0.001(2) O42 0.0508(19) 0.056(2) 0.0527(19) 0.0280(17) 0.0089(16) 0.0190(16) C43 0.053(3) 0.052(3) 0.045(3) 0.018(2) 0.005(2) 0.012(2) C44 0.057(3) 0.045(3) 0.043(3) 0.011(2) 0.004(2) 0.012(2) C45 0.043(3) 0.040(3) 0.039(2) 0.007(2) -0.001(2) 0.007(2) C46 0.040(3) 0.039(2) 0.039(2) 0.008(2) -0.001(2) 0.001(2) C47 0.040(3) 0.047(3) 0.040(3) 0.014(2) 0.003(2) 0.005(2) C48 0.041(3) 0.044(3) 0.039(3) 0.010(2) 0.003(2) 0.012(2) N49 0.039(2) 0.039(2) 0.0320(19) 0.0127(16) 0.0024(16) 0.0030(17) C50 0.049(3) 0.048(3) 0.046(3) 0.017(2) 0.003(2) 0.006(2) C51 0.040(3) 0.038(2) 0.032(2) 0.006(2) -0.002(2) 0.0044(19) C52 0.040(3) 0.039(2) 0.032(2) 0.008(2) -0.0012(19) 0.005(2) C53 0.035(2) 0.040(2) 0.035(2) 0.010(2) 0.0033(19) 0.010(2) N54 0.041(2) 0.047(2) 0.046(2) 0.0187(18) 0.0086(18) 0.0142(18) N55 0.044(2) 0.044(2) 0.057(2) 0.0205(19) 0.007(2) 0.0100(18) N56 0.039(2) 0.034(2) 0.042(2) 0.0121(17) 0.0035(17) 0.0074(16) C57 0.039(3) 0.040(2) 0.045(3) 0.014(2) 0.008(2) 0.011(2) C58 0.043(3) 0.041(3) 0.052(3) 0.015(2) 0.011(2) 0.006(2) C59 0.054(3) 0.050(3) 0.052(3) 0.021(2) 0.013(2) 0.008(2) C60 0.061(3) 0.060(3) 0.060(3) 0.027(3) 0.002(3) -0.006(3) C61 0.056(3) 0.054(3) 0.059(3) 0.019(3) -0.001(3) 0.001(2) C62 0.042(3) 0.062(3) 0.058(3) 0.015(3) 0.003(2) 0.010(2) C63 0.051(3) 0.063(3) 0.054(3) 0.013(3) 0.005(2) 0.010(3) C64 0.039(2) 0.040(2) 0.032(2) 0.0084(19) -0.0024(19) 0.003(2) C65 0.035(2) 0.034(2) 0.034(2) 0.0059(19) 0.0005(19) 0.0008(19) C66 0.035(2) 0.044(3) 0.032(2) 0.008(2) 0.0005(18) 0.007(2) C67 0.030(2) 0.045(3) 0.035(2) 0.011(2) -0.0001(19) 0.0042(19) N68 0.043(2) 0.050(2) 0.052(2) 0.0172(19) 0.0036(19) 0.0100(19) N69 0.047(2) 0.050(2) 0.055(2) 0.016(2) 0.0093(19) 0.012(2) N70 0.042(2) 0.039(2) 0.042(2) 0.0099(18) 0.0009(18) 0.0074(18) C71 0.033(2) 0.046(3) 0.040(2) 0.013(2) 0.0037(19) 0.007(2) C72 0.050(3) 0.037(3) 0.062(3) 0.010(2) 0.003(2) 0.013(2) C73 0.043(3) 0.042(3) 0.051(3) 0.013(2) 0.005(2) 0.011(2) C74 0.041(3) 0.034(2) 0.059(3) 0.011(2) 0.005(2) 0.004(2) C75 0.050(3) 0.043(3) 0.054(3) 0.014(2) 0.011(2) 0.011(2) C76 0.076(4) 0.045(3) 0.052(3) 0.017(2) 0.008(3) 0.018(3) C77 0.073(4) 0.060(3) 0.057(3) 0.018(3) 0.006(3) 0.023(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4211(9) 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 O2 . C3 . 1.432(5) yes O2 . C44 . 1.407(5) yes C3 . C4 . 1.503(6) yes C3 . H31 . 0.973 no C3 . H32 . 0.996 no C4 . O5 . 1.424(5) yes C4 . H41 . 0.978 no C4 . H42 . 0.971 no O5 . C6 . 1.432(5) yes C6 . C7 . 1.505(7) yes C6 . H61 . 0.986 no C6 . H62 . 1.020 no C7 . O8 . 1.432(5) yes C7 . H71 . 0.987 no C7 . H72 . 0.996 no O8 . C9 . 1.425(5) yes C9 . C10 . 1.491(6) yes C9 . H91 . 0.978 no C9 . H92 . 0.972 no C10 . O11 . 1.434(5) yes C10 . H101 . 1.004 no C10 . H102 . 0.978 no O11 . C12 . 1.376(5) yes C12 . C13 . 1.390(6) yes C12 . C48 . 1.368(6) yes C13 . C14 . 1.371(6) yes C13 . H131 . 0.983 no C14 . C15 . 1.377(6) yes C14 . H141 . 0.956 no C15 . O16 . 1.384(5) yes C15 . C47 . 1.391(6) yes O16 . C17 . 1.416(5) yes C17 . C18 . 1.502(6) yes C17 . H171 . 0.988 no C17 . H172 . 0.981 no C18 . N19 . 1.460(6) yes C18 . H181 . 1.007 no C18 . H182 . 0.966 no N19 . C20 . 1.361(6) yes N19 . H191 . 0.916 no C20 . O21 . 1.235(5) yes C20 . C22 . 1.507(6) yes C22 . C23 . 1.399(6) yes C22 . C27 . 1.390(6) yes C23 . C24 . 1.389(6) yes C23 . H231 . 0.938 no C24 . C25 . 1.394(6) yes C24 . C32 . 1.496(6) yes C25 . C26 . 1.390(6) yes C25 . H251 . 0.944 no C26 . C27 . 1.400(6) yes C26 . C28 . 1.523(6) yes C27 . H271 . 0.953 no C28 . C29 . 1.523(7) yes C28 . C30 . 1.526(7) yes C28 . C31 . 1.529(7) yes C29 . H293 . 0.979 no C29 . H292 . 0.954 no C29 . H291 . 0.972 no C30 . H301 . 0.966 no C30 . H302 . 0.988 no C30 . H303 . 0.948 no C31 . H311 . 0.969 no C31 . H312 . 0.997 no C31 . H313 . 0.986 no C32 . O33 . 1.236(5) yes C32 . N34 . 1.342(6) yes N34 . C35 . 1.464(6) yes N34 . H341 . 0.914 no C35 . C36 . 1.500(6) yes C35 . H351 . 1.017 no C35 . H352 . 0.996 no C36 . O37 . 1.415(5) yes C36 . H361 . 1.014 no C36 . H362 . 0.971 no O37 . C38 . 1.382(5) yes C38 . C39 . 1.379(6) yes C38 . C46 . 1.392(6) yes C39 . C40 . 1.386(6) yes C39 . H391 . 1.010 no C40 . C41 . 1.396(6) yes C40 . H401 . 0.982 no C41 . O42 . 1.376(5) yes C41 . C45 . 1.381(6) yes O42 . C43 . 1.412(6) yes C43 . C44 . 1.501(6) yes C43 . H431 . 1.006 no C43 . H432 . 0.987 no C44 . H441 . 1.032 no C44 . H442 . 0.996 no C45 . C46 . 1.389(6) yes C45 . H451 . 0.953 no C46 . H461 . 0.971 no C47 . C48 . 1.391(6) yes C47 . H471 . 0.960 no C48 . H481 . 0.951 no N49 . C50 . 1.477(6) yes N49 . C51 . 1.337(5) yes N49 . C66 . 1.348(5) yes C50 . H501 . 0.962 no C50 . H502 . 0.991 no C50 . H503 . 0.982 no C51 . C52 . 1.382(6) yes C51 . H511 . 0.963 no C52 . C53 . 1.465(6) yes C52 . C64 . 1.390(6) yes C53 . N54 . 1.364(5) yes C53 . C57 . 1.361(6) yes N54 . N55 . 1.318(5) yes N55 . N56 . 1.355(5) yes N56 . C57 . 1.337(5) yes N56 . C58 . 1.456(6) yes C57 . H571 . 0.912 no C58 . C59 . 1.520(7) yes C58 . H581 . 0.969 no C58 . H582 . 0.993 no C59 . C60 . 1.535(7) yes C59 . H591 . 1.001 no C59 . H592 . 0.964 no C60 . C61 . 1.518(7) yes C60 . H601 . 0.994 no C60 . H602 . 0.988 no C61 . C62 . 1.506(7) yes C61 . H611 . 0.979 no C61 . H612 . 0.971 no C62 . C63 . 1.496(7) yes C62 . H621 . 0.965 no C62 . H622 . 0.988 no C63 . H631 . 0.941 no C63 . H632 . 0.966 no C63 . H633 . 0.965 no C64 . C65 . 1.383(6) yes C64 . H641 . 0.948 no C65 . C66 . 1.381(6) yes C65 . C67 . 1.473(6) yes C66 . H661 . 0.957 no C67 . N68 . 1.367(6) yes C67 . C71 . 1.360(6) yes N68 . N69 . 1.316(5) yes N69 . N70 . 1.342(5) yes N70 . C71 . 1.355(6) yes N70 . C72 . 1.457(6) yes C71 . H711 . 0.926 no C72 . C73 . 1.521(7) yes C72 . H721 . 0.991 no C72 . H722 . 0.988 no C73 . C74 . 1.525(6) yes C73 . H731 . 1.000 no C73 . H732 . 0.968 no C74 . C75 . 1.511(7) yes C74 . H741 . 1.008 no C74 . H742 . 0.961 no C75 . C76 . 1.517(7) yes C75 . H751 . 0.994 no C75 . H752 . 0.965 no C76 . C77 . 1.517(7) yes C76 . H761 . 0.980 no C76 . H762 . 0.990 no C77 . H771 . 0.985 no C77 . H772 . 0.994 no C77 . H773 . 0.946 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 C3 . O2 . C44 . 112.8(3) yes O2 . C3 . C4 . 108.5(3) yes O2 . C3 . H31 . 111.8 no C4 . C3 . H31 . 111.3 no O2 . C3 . H32 . 107.7 no C4 . C3 . H32 . 106.4 no H31 . C3 . H32 . 110.9 no C3 . C4 . O5 . 108.9(4) yes C3 . C4 . H41 . 110.3 no O5 . C4 . H41 . 108.5 no C3 . C4 . H42 . 110.4 no O5 . C4 . H42 . 112.2 no H41 . C4 . H42 . 106.5 no C4 . O5 . C6 . 113.2(3) yes O5 . C6 . C7 . 114.5(4) yes O5 . C6 . H61 . 111.0 no C7 . C6 . H61 . 110.2 no O5 . C6 . H62 . 108.1 no C7 . C6 . H62 . 108.6 no H61 . C6 . H62 . 103.9 no C6 . C7 . O8 . 112.0(4) yes C6 . C7 . H71 . 108.3 no O8 . C7 . H71 . 110.2 no C6 . C7 . H72 . 111.0 no O8 . C7 . H72 . 107.0 no H71 . C7 . H72 . 108.4 no C7 . O8 . C9 . 113.1(3) yes O8 . C9 . C10 . 109.7(4) yes O8 . C9 . H91 . 112.6 no C10 . C9 . H91 . 107.8 no O8 . C9 . H92 . 109.7 no C10 . C9 . H92 . 106.9 no H91 . C9 . H92 . 110.0 no C9 . C10 . O11 . 108.2(4) yes C9 . C10 . H101 . 109.7 no O11 . C10 . H101 . 113.3 no C9 . C10 . H102 . 107.1 no O11 . C10 . H102 . 112.5 no H101 . C10 . H102 . 105.8 no C10 . O11 . C12 . 116.3(3) yes O11 . C12 . C13 . 114.7(4) yes O11 . C12 . C48 . 126.2(4) yes C13 . C12 . C48 . 119.1(4) yes C12 . C13 . C14 . 120.5(4) yes C12 . C13 . H131 . 119.9 no C14 . C13 . H131 . 119.6 no C13 . C14 . C15 . 120.6(4) yes C13 . C14 . H141 . 120.0 no C15 . C14 . H141 . 119.4 no C14 . C15 . O16 . 116.4(4) yes C14 . C15 . C47 . 119.5(4) yes O16 . C15 . C47 . 124.2(4) yes C15 . O16 . C17 . 118.5(3) yes O16 . C17 . C18 . 108.5(4) yes O16 . C17 . H171 . 110.8 no C18 . C17 . H171 . 111.3 no O16 . C17 . H172 . 108.0 no C18 . C17 . H172 . 111.0 no H171 . C17 . H172 . 107.3 no C17 . C18 . N19 . 112.7(4) yes C17 . C18 . H181 . 109.4 no N19 . C18 . H181 . 109.2 no C17 . C18 . H182 . 105.5 no N19 . C18 . H182 . 107.7 no H181 . C18 . H182 . 112.4 no C18 . N19 . C20 . 117.6(4) yes C18 . N19 . H191 . 121.1 no C20 . N19 . H191 . 121.3 no N19 . C20 . O21 . 121.1(4) yes N19 . C20 . C22 . 117.6(4) yes O21 . C20 . C22 . 121.2(4) yes C20 . C22 . C23 . 123.3(4) yes C20 . C22 . C27 . 116.8(4) yes C23 . C22 . C27 . 119.5(4) yes C22 . C23 . C24 . 119.4(4) yes C22 . C23 . H231 . 119.9 no C24 . C23 . H231 . 120.7 no C23 . C24 . C25 . 119.7(4) yes C23 . C24 . C32 . 123.2(4) yes C25 . C24 . C32 . 117.0(4) yes C24 . C25 . C26 . 122.4(4) yes C24 . C25 . H251 . 117.4 no C26 . C25 . H251 . 120.2 no C25 . C26 . C27 . 116.7(4) yes C25 . C26 . C28 . 123.3(4) yes C27 . C26 . C28 . 119.9(4) yes C26 . C27 . C22 . 122.3(4) yes C26 . C27 . H271 . 119.1 no C22 . C27 . H271 . 118.6 no C26 . C28 . C29 . 110.6(4) yes C26 . C28 . C30 . 108.2(4) yes C29 . C28 . C30 . 109.8(5) yes C26 . C28 . C31 . 111.4(4) yes C29 . C28 . C31 . 110.0(5) yes C30 . C28 . C31 . 106.7(4) yes C28 . C29 . H293 . 108.0 no C28 . C29 . H292 . 112.5 no H293 . C29 . H292 . 108.4 no C28 . C29 . H291 . 109.7 no H293 . C29 . H291 . 108.5 no H292 . C29 . H291 . 109.6 no C28 . C30 . H301 . 110.0 no C28 . C30 . H302 . 110.4 no H301 . C30 . H302 . 105.4 no C28 . C30 . H303 . 111.4 no H301 . C30 . H303 . 110.6 no H302 . C30 . H303 . 108.9 no C28 . C31 . H311 . 111.5 no C28 . C31 . H312 . 109.4 no H311 . C31 . H312 . 108.3 no C28 . C31 . H313 . 109.5 no H311 . C31 . H313 . 110.4 no H312 . C31 . H313 . 107.7 no C24 . C32 . O33 . 121.2(4) yes C24 . C32 . N34 . 117.5(4) yes O33 . C32 . N34 . 121.3(4) yes C32 . N34 . C35 . 121.0(4) yes C32 . N34 . H341 . 119.4 no C35 . N34 . H341 . 119.6 no N34 . C35 . C36 . 110.7(4) yes N34 . C35 . H351 . 110.7 no C36 . C35 . H351 . 110.0 no N34 . C35 . H352 . 106.5 no C36 . C35 . H352 . 111.0 no H351 . C35 . H352 . 107.9 no C35 . C36 . O37 . 108.3(4) yes C35 . C36 . H361 . 110.6 no O37 . C36 . H361 . 111.5 no C35 . C36 . H362 . 109.0 no O37 . C36 . H362 . 110.1 no H361 . C36 . H362 . 107.3 no C36 . O37 . C38 . 117.5(3) yes O37 . C38 . C39 . 115.5(4) yes O37 . C38 . C46 . 124.2(4) yes C39 . C38 . C46 . 120.3(4) yes C38 . C39 . C40 . 120.8(4) yes C38 . C39 . H391 . 118.2 no C40 . C39 . H391 . 121.0 no C39 . C40 . C41 . 119.3(4) yes C39 . C40 . H401 . 121.1 no C41 . C40 . H401 . 119.6 no C40 . C41 . O42 . 123.9(4) yes C40 . C41 . C45 . 119.7(4) yes O42 . C41 . C45 . 116.4(4) yes C41 . O42 . C43 . 117.7(3) yes O42 . C43 . C44 . 108.6(4) yes O42 . C43 . H431 . 113.4 no C44 . C43 . H431 . 108.6 no O42 . C43 . H432 . 108.7 no C44 . C43 . H432 . 110.1 no H431 . C43 . H432 . 107.4 no C43 . C44 . O2 . 109.0(4) yes C43 . C44 . H441 . 110.0 no O2 . C44 . H441 . 110.9 no C43 . C44 . H442 . 109.4 no O2 . C44 . H442 . 109.0 no H441 . C44 . H442 . 108.4 no C41 . C45 . C46 . 121.1(4) yes C41 . C45 . H451 . 121.8 no C46 . C45 . H451 . 117.1 no C38 . C46 . C45 . 118.9(4) yes C38 . C46 . H461 . 120.4 no C45 . C46 . H461 . 120.7 no C15 . C47 . C48 . 119.4(4) yes C15 . C47 . H471 . 120.5 no C48 . C47 . H471 . 120.1 no C47 . C48 . C12 . 120.9(4) yes C47 . C48 . H481 . 118.1 no C12 . C48 . H481 . 120.9 no C50 . N49 . C51 . 119.0(4) yes C50 . N49 . C66 . 119.7(4) yes C51 . N49 . C66 . 121.3(4) yes N49 . C50 . H501 . 111.2 no N49 . C50 . H502 . 111.2 no H501 . C50 . H502 . 108.1 no N49 . C50 . H503 . 110.9 no H501 . C50 . H503 . 106.9 no H502 . C50 . H503 . 108.3 no N49 . C51 . C52 . 121.1(4) yes N49 . C51 . H511 . 117.9 no C52 . C51 . H511 . 121.0 no C51 . C52 . C53 . 120.6(4) yes C51 . C52 . C64 . 117.8(4) yes C53 . C52 . C64 . 121.5(4) yes C52 . C53 . N54 . 122.0(4) yes C52 . C53 . C57 . 129.0(4) yes N54 . C53 . C57 . 108.9(4) yes C53 . N54 . N55 . 108.1(4) yes N54 . N55 . N56 . 107.2(3) yes N55 . N56 . C57 . 110.7(4) yes N55 . N56 . C58 . 121.0(3) yes C57 . N56 . C58 . 128.3(4) yes C53 . C57 . N56 . 105.2(4) yes C53 . C57 . H571 . 126.8 no N56 . C57 . H571 . 128.0 no N56 . C58 . C59 . 112.7(4) yes N56 . C58 . H581 . 111.9 no C59 . C58 . H581 . 107.9 no N56 . C58 . H582 . 109.9 no C59 . C58 . H582 . 107.0 no H581 . C58 . H582 . 107.1 no C58 . C59 . C60 . 111.5(4) yes C58 . C59 . H591 . 112.1 no C60 . C59 . H591 . 109.7 no C58 . C59 . H592 . 105.8 no C60 . C59 . H592 . 107.9 no H591 . C59 . H592 . 109.9 no C59 . C60 . C61 . 114.2(4) yes C59 . C60 . H601 . 109.0 no C61 . C60 . H601 . 107.4 no C59 . C60 . H602 . 108.8 no C61 . C60 . H602 . 110.5 no H601 . C60 . H602 . 106.7 no C60 . C61 . C62 . 114.6(4) yes C60 . C61 . H611 . 108.2 no C62 . C61 . H611 . 108.1 no C60 . C61 . H612 . 108.7 no C62 . C61 . H612 . 108.9 no H611 . C61 . H612 . 108.1 no C61 . C62 . C63 . 115.5(4) yes C61 . C62 . H621 . 106.1 no C63 . C62 . H621 . 110.9 no C61 . C62 . H622 . 107.1 no C63 . C62 . H622 . 110.0 no H621 . C62 . H622 . 106.9 no C62 . C63 . H631 . 111.4 no C62 . C63 . H632 . 113.3 no H631 . C63 . H632 . 107.0 no C62 . C63 . H633 . 110.1 no H631 . C63 . H633 . 107.9 no H632 . C63 . H633 . 106.8 no C52 . C64 . C65 . 120.9(4) yes C52 . C64 . H641 . 118.2 no C65 . C64 . H641 . 120.9 no C64 . C65 . C66 . 118.3(4) yes C64 . C65 . C67 . 121.1(4) yes C66 . C65 . C67 . 120.6(4) yes C65 . C66 . N49 . 120.6(4) yes C65 . C66 . H661 . 121.7 no N49 . C66 . H661 . 117.7 no C65 . C67 . N68 . 122.0(4) yes C65 . C67 . C71 . 128.8(4) yes N68 . C67 . C71 . 108.7(4) yes C67 . N68 . N69 . 108.4(4) yes N68 . N69 . N70 . 107.5(3) yes N69 . N70 . C71 . 110.6(4) yes N69 . N70 . C72 . 121.0(4) yes C71 . N70 . C72 . 128.2(4) yes C67 . C71 . N70 . 104.8(4) yes C67 . C71 . H711 . 129.2 no N70 . C71 . H711 . 126.0 no N70 . C72 . C73 . 115.1(4) yes N70 . C72 . H721 . 105.8 no C73 . C72 . H721 . 107.9 no N70 . C72 . H722 . 108.8 no C73 . C72 . H722 . 108.9 no H721 . C72 . H722 . 110.2 no C72 . C73 . C74 . 110.4(4) yes C72 . C73 . H731 . 110.6 no C74 . C73 . H731 . 108.4 no C72 . C73 . H732 . 110.0 no C74 . C73 . H732 . 109.0 no H731 . C73 . H732 . 108.4 no C73 . C74 . C75 . 113.2(4) yes C73 . C74 . H741 . 107.6 no C75 . C74 . H741 . 112.7 no C73 . C74 . H742 . 106.8 no C75 . C74 . H742 . 107.4 no H741 . C74 . H742 . 108.8 no C74 . C75 . C76 . 113.9(4) yes C74 . C75 . H751 . 110.3 no C76 . C75 . H751 . 104.9 no C74 . C75 . H752 . 109.2 no C76 . C75 . H752 . 109.3 no H751 . C75 . H752 . 109.1 no C75 . C76 . C77 . 113.3(4) yes C75 . C76 . H761 . 109.3 no C77 . C76 . H761 . 111.4 no C75 . C76 . H762 . 110.3 no C77 . C76 . H762 . 106.5 no H761 . C76 . H762 . 105.7 no C76 . C77 . H771 . 108.6 no C76 . C77 . H772 . 107.6 no H771 . C77 . H772 . 107.1 no C76 . C77 . H773 . 111.0 no H771 . C77 . H773 . 111.5 no H772 . C77 . H773 . 110.8 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 C6 . H61 . O33 1_565 135 0.99 2.47 3.243(7) yes C14 . H141 . N55 1_655 168 0.96 2.60 3.536(7) yes C40 . H401 . O33 2_656 153 0.98 2.44 3.345(7) yes C50 . H502 . O5 2_666 150 0.99 2.60 3.487(7) yes C50 . H503 . O2 . 172 0.98 2.41 3.379(7) yes C58 . H581 . O16 1_455 161 0.97 2.49 3.417(7) yes C66 . H661 . O5 2_666 162 0.96 2.37 3.289(7) yes data_5Cl _database_code_depnum_ccdc_archive 'CCDC 885862' #TrackingRef 'White_Beer.cif' #============================================================================== _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 ; One half of one macrocycle is disordered; this was modelled by having two positions (occupancy 0.65:0.35) for these atoms, with restraints on bond lengths and angles being applied. Despite this, there is some residual electron density around this area. ; _cell_length_a 11.4693(3) _cell_length_b 16.2473(5) _cell_length_c 20.3444(8) _cell_angle_alpha 97.255(3) _cell_angle_beta 105.022(3) _cell_angle_gamma 99.338(2) _cell_volume 3556.2(2) _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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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' Cl 0.3639 0.7018 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 = C60 H70 Cl1 N9 O15 # Dc = 1.11 Fooo = 1468.00 Mu = 10.01 M = 1192.72 # Found Formula = C72 H90 Cl1 N9 O16.50 # Dc = 1.29 FOOO = 1468.00 Mu = 10.88 M = 1381.01 _chemical_formula_sum 'C72 H90 Cl1 N9 O16.50' _chemical_formula_moiety 'C34 H38 N7 O6, C32 H37 N2 O9, 1.5(C4 H10 O), Cl' _chemical_compound_source synthesized _chemical_formula_weight 1381.01 _cell_measurement_reflns_used 12735 _cell_measurement_theta_min 4 _cell_measurement_theta_max 77 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_max 0.320 _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1468.001 _exptl_absorpt_coefficient_mu 1.088 # Sheldrick geometric approximatio 0.74 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro, (Oxford Diffraction, 2011)' _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _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 'CrysAlisPro, (Oxford Diffraction, 2011)' _computing_data_reduction 'CrysAlisPro, (Oxford Diffraction, 2011)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 37560 _reflns_number_total 14781 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 14781 # Theoretical number of reflections is about 22437 _diffrn_reflns_theta_min 3.916 _diffrn_reflns_theta_max 76.984 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 73.904 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -14 _reflns_limit_h_max 13 _reflns_limit_k_min -20 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 3.83 _oxford_diffrn_Wilson_scale 0.18 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.76 _refine_diff_density_max 1.32 # 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 11201 _refine_ls_number_restraints 722 _refine_ls_number_parameters 1090 _oxford_refine_ls_R_factor_ref 0.0888 _refine_ls_wR_factor_ref 0.2233 _refine_ls_goodness_of_fit_ref 0.9666 _refine_ls_shift/su_max 0.0010969 _refine_ls_shift/su_mean 0.0000446 # The values computed with all filters except I/sigma _oxford_reflns_number_all 11202 _refine_ls_R_factor_all 0.0888 _refine_ls_wR_factor_all 0.2234 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 8953 _refine_ls_R_factor_gt 0.0760 _refine_ls_wR_factor_gt 0.2071 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.13P)^2^ + 3.49P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order 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 C1 C 0.4546(4) 0.6834(2) 0.3112(2) 0.0562 1.0000 Uani . . . . . . C2 C 0.4334(4) 0.6585(3) 0.2401(2) 0.0711 1.0000 Uani . . . . . . C3 C 0.5181(5) 0.6202(3) 0.2159(2) 0.0758 1.0000 Uani . . . . . . C4 C 0.6220(4) 0.6075(2) 0.2595(2) 0.0650 1.0000 Uani . . . . . . C5 C 0.6448(4) 0.6311(2) 0.3303(2) 0.0599 1.0000 Uani . . . . . . C6 C 0.5599(4) 0.6693(2) 0.35542(19) 0.0536 1.0000 Uani . . . . . . O7 O 0.8232(3) 0.5711(2) 0.35226(19) 0.0833 1.0000 Uani . . . . . . C8 C 0.7598(4) 0.6143(2) 0.3758(2) 0.0643 1.0000 Uani . . . . . . N9 N 0.7916(3) 0.6485(2) 0.44286(19) 0.0633 1.0000 Uani . . . . . . C10 C 0.9029(4) 0.6335(3) 0.4899(3) 0.0676 1.0000 Uani . . . . . . C11 C 0.9168(4) 0.6714(3) 0.5627(3) 0.0654 1.0000 Uani . . . . . . O12 O 0.9627(3) 0.76128(17) 0.57144(16) 0.0649 1.0000 Uani . . . . . . C13 C 0.9970(3) 0.8053(3) 0.6373(2) 0.0586 1.0000 Uani . . . . . . C14 C 1.0653(3) 0.8877(3) 0.6480(2) 0.0577 1.0000 Uani . . . . . . C15 C 1.1043(4) 0.9368(3) 0.7121(2) 0.0629 1.0000 Uani . U . . . . C16 C 1.0777(4) 0.9051(3) 0.7684(2) 0.0687 1.0000 Uani . U . . . . C17 C 1.0106(4) 0.8239(3) 0.7584(2) 0.0681 1.0000 Uani . U . . . . C18 C 0.9703(4) 0.7741(3) 0.6936(2) 0.0654 1.0000 Uani . . . . . . O19 O 1.1208(3) 0.9597(3) 0.83075(15) 0.0856 1.0000 Uani . U . . . . C20 C 1.0945(5) 0.9287(5) 0.8891(2) 0.1004 1.0000 Uani . U . . . . C21 C 1.1506(6) 0.9959(6) 0.9513(3) 0.1191 1.0000 Uani . U . . . . O22 O 1.0901(4) 1.0667(3) 0.94478(16) 0.1101 1.0000 Uani . U . . . . C23 C 1.1367(6) 1.1295(6) 1.0049(3) 0.1323 1.0000 Uani . U . . . . C24 C 1.0875(7) 1.2060(6) 0.9953(3) 0.1335 1.0000 Uani . U . . . . O25 O 0.9588(4) 1.1907(3) 0.98736(17) 0.1049 1.0000 Uani . U . . . . C26 C 0.9071(9) 1.2639(4) 0.9775(3) 0.1296 1.0000 Uani . U . . . . C27 C 0.7731(7) 1.2417(4) 0.9645(3) 0.1092 1.0000 Uani . U . . . . O28 O 0.7211(5) 1.1959(2) 0.89601(17) 0.1068 1.0000 Uani . U . . . . C29 C 0.5906(8) 1.1714(5) 0.8785(3) 0.1287 1.0000 Uani . U . . . . C30 C 0.5457(8) 1.1355(5) 0.8016(3) 0.1428 1.0000 Uani . U . . . . O31 O 0.5760(3) 1.0575(2) 0.79086(14) 0.0732 1.0000 Uani . U . . . . C32 C 0.5309(4) 1.0149(3) 0.72292(18) 0.0567 1.0000 Uani . U . . . . C33 C 0.4594(4) 0.9350(3) 0.70945(19) 0.0605 1.0000 Uani . U . . . . C34 C 0.4175(4) 0.8883(2) 0.64351(18) 0.0550 1.0000 Uani . . . . . . C35 C 0.4464(3) 0.9231(2) 0.58904(17) 0.0453 1.0000 Uani . . . . . . C36 C 0.5191(3) 1.0039(2) 0.60243(17) 0.0440 1.0000 Uani . . . . . . C37 C 0.5618(3) 1.0498(2) 0.66882(18) 0.0505 1.0000 Uani . . . . . . O38 O 0.4070(2) 0.88329(14) 0.52152(11) 0.0468 1.0000 Uani . . . . . . C39 C 0.3186(3) 0.8052(2) 0.50523(18) 0.0483 1.0000 Uani . . . . . . C40 C 0.2797(3) 0.7761(2) 0.42811(18) 0.0512 1.0000 Uani . . . . . . N41 N 0.3755(3) 0.74498(18) 0.40359(14) 0.0502 1.0000 Uani . . . . . . C42 C 0.3594(4) 0.7237(2) 0.33531(18) 0.0546 1.0000 Uani . . . . . . O43 O 0.2699(3) 0.7377(2) 0.29287(14) 0.0710 1.0000 Uani . . . . . . C51 C 0.0940(5) -0.1284(3) 0.1848(2) 0.0772 1.0000 Uani . . . . . . N52 N 0.1444(3) -0.04778(19) 0.23509(14) 0.0515 1.0000 Uani . . . . . . C53 C 0.1913(3) 0.0221(2) 0.21488(17) 0.0517 1.0000 Uani . . . . . . C54 C 0.2407(3) 0.0969(2) 0.26156(16) 0.0429 1.0000 Uani . . . . . . C55 C 0.2412(3) 0.09755(19) 0.32967(16) 0.0386 1.0000 Uani . . . . . . C56 C 0.1912(3) 0.0243(2) 0.35010(16) 0.0385 1.0000 Uani . . . . . . C57 C 0.1420(3) -0.0481(2) 0.30079(17) 0.0469 1.0000 Uani . . . . . . C58 C 0.2869(3) 0.1747(2) 0.23864(17) 0.0457 1.0000 Uani . U . . . . C59 C 0.3402(3) 0.2534(2) 0.27624(18) 0.0451 1.0000 Uani . U . . . . N60 N 0.2758(4) 0.1781(2) 0.17149(17) 0.0799 1.0000 Uani . U . . . . N61 N 0.3190(5) 0.2563(3) 0.16634(18) 0.0870 1.0000 Uani . U . . . . N62 N 0.3575(3) 0.30180(19) 0.22958(15) 0.0532 1.0000 Uani D U . . . . C63 C 0.4206(11) 0.3919(6) 0.2518(9) 0.0562 0.3500 Uani D U . . 1 . C64 C 0.3249(10) 0.4459(7) 0.2351(6) 0.0715 0.3500 Uani D U . . 1 . O65 O 0.2281(8) 0.4190(5) 0.2644(5) 0.0738 0.3500 Uani D U . . 1 . C66 C 0.2347(10) 0.4673(6) 0.3282(7) 0.0561 0.3500 Uani D U . . 1 . C67 C 0.3382(13) 0.4939(7) 0.3862(7) 0.0648 0.3500 Uani D U . . 1 . C68 C 0.3295(12) 0.5381(7) 0.4474(7) 0.0586 0.3500 Uani D U . . 1 . C69 C 0.2198(12) 0.5568(7) 0.4569(7) 0.0616 0.3500 Uani D U . . 1 . C70 C 0.1170(14) 0.5295(7) 0.3983(7) 0.0633 0.3500 Uani D U . . 1 . C71 C 0.1230(13) 0.4853(7) 0.3359(8) 0.0687 0.3500 Uani D U . . 1 . O72 O 0.2070(11) 0.6014(6) 0.5214(5) 0.0623 0.3500 Uani D U . . 1 . C73 C 0.2933(15) 0.5984(11) 0.5811(7) 0.0745 0.3500 Uani D U . . 1 . C74 C 0.2516(9) 0.6514(9) 0.6314(6) 0.0630 0.3500 Uani D U . . 1 . O75 O 0.3531(6) 0.6740(6) 0.6904(5) 0.0765 0.3500 Uani D U . . 1 . C76 C 0.3114(16) 0.6308(8) 0.7359(7) 0.1142 0.3500 Uani D U . . 1 . C77 C 0.2807(16) 0.6916(12) 0.7886(9) 0.1540 0.3500 Uani D U . . 1 . C78 C 0.1670(16) 0.6801(11) 0.7990(10) 0.1400 0.3500 Uani D U . . 1 . C79 C 0.127(2) 0.6396(10) 0.8565(8) 0.1720 0.3500 Uani D U . . 1 . O80 O 0.0776(13) 0.5516(7) 0.8308(6) 0.1194 0.3500 Uani D U . . 1 . C81 C -0.0165(13) 0.5166(7) 0.8584(8) 0.0899 0.3500 Uani D U . . 1 . C82 C -0.0583(9) 0.4211(8) 0.8309(9) 0.1137 0.3500 Uani D U . . 1 . O83 O 0.0473(3) 0.3848(2) 0.85193(18) 0.0893 1.0000 Uani D U . . . . C84 C 0.0856(4) 0.3268(2) 0.8092(2) 0.0644 1.0000 Uani . U . . . . C85 C 0.0299(4) 0.3014(2) 0.7395(2) 0.0607 1.0000 Uani . U . . . . C86 C 0.0758(3) 0.2434(2) 0.70136(19) 0.0525 1.0000 Uani . U . . . . C87 C 0.1759(3) 0.2114(2) 0.73352(17) 0.0483 1.0000 Uani D U . . . . C88 C 0.2298(4) 0.2359(2) 0.80373(19) 0.0574 1.0000 Uani . U . . . . C89 C 0.1852(4) 0.2938(3) 0.8414(2) 0.0651 1.0000 Uani . U . . . . O90 O 0.2294(2) 0.15593(16) 0.69976(11) 0.0513 1.0000 Uani D U . . . . C91 C 0.1814(3) 0.1328(2) 0.62678(16) 0.0444 1.0000 Uani . U . . . . C92 C 0.2691(3) 0.0825(2) 0.60538(16) 0.0446 1.0000 Uani . U . . . . N93 N 0.2285(2) 0.04727(16) 0.53186(13) 0.0388 1.0000 Uani . U . . . . N94 N 0.1569(3) -0.03054(17) 0.50856(14) 0.0439 1.0000 Uani . U . . . . N95 N 0.1359(2) -0.04608(17) 0.44171(13) 0.0418 1.0000 Uani . U . . . . C96 C 0.2531(3) 0.0824(2) 0.47952(16) 0.0402 1.0000 Uani . U . . . . C97 C 0.1938(3) 0.02236(19) 0.42188(15) 0.0366 1.0000 Uani . U . . . . C101 C 0.4587(10) 0.3052(7) 0.0189(5) 0.1845 1.0000 Uani D U . . . . C102 C 0.5506(7) 0.3852(5) 0.0498(4) 0.1328 1.0000 Uani D U . . . . O103 O 0.6058(4) 0.4128(3) -0.0023(3) 0.1167 1.0000 Uani . U . . . . C104 C 0.6982(10) 0.4849(6) 0.0269(5) 0.1728 1.0000 Uani D U . . . . C105 C 0.7549(9) 0.5062(6) -0.0299(5) 0.1650 1.0000 Uani D U . . . . Cl1 Cl 0.60412(8) 0.71554(5) 0.53737(4) 0.0477 1.0000 Uani . . . . . . C173 C 0.2837(8) 0.6229(6) 0.5994(4) 0.0714 0.6500 Uani D U . . 2 . C174 C 0.2239(8) 0.6537(9) 0.6563(4) 0.1009 0.6500 Uani D U . . 2 . O175 O 0.3184(5) 0.6903(5) 0.7265(4) 0.1190 0.6500 Uani D U . . 2 . C176 C 0.2902(10) 0.6426(6) 0.7761(5) 0.1269 0.6500 Uani D U . . 2 . C177 C 0.1993(8) 0.6688(8) 0.8082(5) 0.1382 0.6500 Uani D U . . 2 . C178 C 0.1133(8) 0.6026(7) 0.8053(5) 0.1207 0.6500 Uani D U . . 2 . C179 C 0.0093(7) 0.6089(6) 0.8333(3) 0.0938 0.6500 Uani D U . . 2 . O180 O 0.0114(9) 0.5558(5) 0.8823(4) 0.1432 0.6500 Uani D U . . 2 . C181 C -0.0880(9) 0.4872(6) 0.8611(6) 0.1350 0.6500 Uani D U . . 2 . C182 C -0.0597(10) 0.4173(7) 0.8148(5) 0.1052 0.6500 Uani D U . . 2 . O172 O 0.1846(7) 0.6055(5) 0.5355(4) 0.0758 0.6500 Uani D U . . 2 . C169 C 0.2216(6) 0.5704(5) 0.4834(4) 0.0609 0.6500 Uani D U . . 2 . C170 C 0.1296(9) 0.5405(5) 0.4204(4) 0.0625 0.6500 Uani D U . . 2 . C168 C 0.3413(6) 0.5590(4) 0.4842(3) 0.0518 0.6500 Uani D U . . 2 . C171 C 0.1544(5) 0.5007(4) 0.3627(4) 0.0548 0.6500 Uani D U . . 2 . C166 C 0.2732(5) 0.4891(3) 0.3651(3) 0.0454 0.6500 Uani D U . . 2 . C167 C 0.3665(5) 0.5196(4) 0.4263(3) 0.0489 0.6500 Uani D U . . 2 . O165 O 0.2862(3) 0.4463(2) 0.3043(2) 0.0498 0.6500 Uani D U . . 2 . C164 C 0.4087(4) 0.4407(3) 0.3052(3) 0.0472 0.6500 Uani D U . . 2 . C163 C 0.4070(7) 0.3933(4) 0.2351(4) 0.0510 0.6500 Uani D U . . 2 . H21 H 0.3622 0.6690 0.2111 0.0835 1.0000 Uiso R . . . . . H31 H 0.5029 0.6020 0.1694 0.0882 1.0000 Uiso R . . . . . H41 H 0.6791 0.5838 0.2419 0.0773 1.0000 Uiso R . . . . . H61 H 0.5727 0.6845 0.4026 0.0632 1.0000 Uiso R . . . . . H102 H 0.9763 0.6598 0.4775 0.0808 1.0000 Uiso R . . . . . H101 H 0.8983 0.5728 0.4860 0.0806 1.0000 Uiso R . . . . . H111 H 0.9751 0.6475 0.5962 0.0763 1.0000 Uiso R . . . . . H112 H 0.8367 0.6626 0.5720 0.0759 1.0000 Uiso R . . . . . H141 H 1.0845 0.9087 0.6121 0.0670 1.0000 Uiso R . . . . . H151 H 1.1482 0.9920 0.7178 0.0734 1.0000 Uiso R . . . . . H171 H 0.9924 0.8021 0.7951 0.0818 1.0000 Uiso R . . . . . H181 H 0.9261 0.7181 0.6876 0.0735 1.0000 Uiso R . . . . . H201 H 1.1326 0.8796 0.8952 0.1180 1.0000 Uiso R . . . . . H202 H 1.0048 0.9133 0.8806 0.1185 1.0000 Uiso R . . . . . H212 H 1.2361 1.0162 0.9547 0.1391 1.0000 Uiso R . . . . . H211 H 1.1493 0.9744 0.9937 0.1393 1.0000 Uiso R . . . . . H231 H 1.2268 1.1425 1.0155 0.1561 1.0000 Uiso R . . . . . H232 H 1.1115 1.1078 1.0426 0.1560 1.0000 Uiso R . . . . . H241 H 1.1332 1.2576 0.9962 0.1564 1.0000 Uiso R . . . . . H261 H 0.9424 1.3063 1.0208 0.1537 1.0000 Uiso R . . . . . H262 H 0.9267 1.2860 0.9383 0.1546 1.0000 Uiso R . . . . . H272 H 0.7388 1.2918 0.9710 0.1273 1.0000 Uiso R . . . . . H271 H 0.7555 1.2054 0.9973 0.1268 1.0000 Uiso R . . . . . H292 H 0.5511 1.2186 0.8881 0.1539 1.0000 Uiso R . . . . . H291 H 0.5716 1.1280 0.9051 0.1542 1.0000 Uiso R . . . . . H301 H 0.5867 1.1736 0.7769 0.1591 1.0000 Uiso R . . . . . H302 H 0.4541 1.1276 0.7836 0.1589 1.0000 Uiso R . . . . . H331 H 0.4400 0.9115 0.7452 0.0715 1.0000 Uiso R . . . . . H341 H 0.3702 0.8334 0.6347 0.0641 1.0000 Uiso R . . . . . H361 H 0.5366 1.0272 0.5652 0.0517 1.0000 Uiso R . . . . . H371 H 0.6097 1.1035 0.6779 0.0575 1.0000 Uiso R . . . . . H392 H 0.2496 0.8140 0.5215 0.0566 1.0000 Uiso R . . . . . H391 H 0.3561 0.7622 0.5282 0.0567 1.0000 Uiso R . . . . . H401 H 0.2624 0.8252 0.4075 0.0598 1.0000 Uiso R . . . . . H402 H 0.2051 0.7322 0.4154 0.0600 1.0000 Uiso R . . . . . H511 H 0.0869 -0.1750 0.2082 0.1124 1.0000 Uiso R . . . . . H512 H 0.1481 -0.1365 0.1574 0.1121 1.0000 Uiso R . . . . . H513 H 0.0146 -0.1275 0.1560 0.1125 1.0000 Uiso R . . . . . H531 H 0.1897 0.0205 0.1686 0.0596 1.0000 Uiso R . . . . . H551 H 0.2768 0.1483 0.3634 0.0458 1.0000 Uiso R . . . . . H571 H 0.1072 -0.0980 0.3121 0.0550 1.0000 Uiso R . . . . . H591 H 0.3593 0.2711 0.3243 0.0537 1.0000 Uiso R . . . . . H631 H 0.4478 0.4008 0.3027 0.0741 0.3500 Uiso R . . . 1 . H632 H 0.4935 0.4077 0.2351 0.0743 0.3500 Uiso R . . . 1 . H642 H 0.3610 0.5052 0.2539 0.0809 0.3500 Uiso R . . . 1 . H641 H 0.2964 0.4382 0.1844 0.0810 0.3500 Uiso R . . . 1 . H671 H 0.4138 0.4815 0.3829 0.0699 0.3500 Uiso R . . . 1 . H681 H 0.4012 0.5560 0.4838 0.0660 0.3500 Uiso R . . . 1 . H701 H 0.0419 0.5423 0.4021 0.0670 0.3500 Uiso R . . . 1 . H711 H 0.0521 0.4679 0.2990 0.0640 0.3500 Uiso R . . . 1 . H732 H 0.3634 0.6364 0.5753 0.0861 0.3500 Uiso R . . . 1 . H731 H 0.3167 0.5450 0.5908 0.0858 0.3500 Uiso R . . . 1 . H741 H 0.2201 0.7007 0.6179 0.0749 0.3500 Uiso R . . . 1 . H742 H 0.1848 0.6111 0.6385 0.0749 0.3500 Uiso R . . . 1 . H761 H 0.3751 0.6057 0.7636 0.1531 0.3500 Uiso R . . . 1 . H762 H 0.2386 0.5870 0.7117 0.1531 0.3500 Uiso R . . . 1 . H771 H 0.3375 0.7413 0.8104 0.1531 0.3500 Uiso R . . . 1 . H781 H 0.1043 0.7016 0.7714 0.1551 0.3500 Uiso R . . . 1 . H791 H 0.0663 0.6632 0.8740 0.2000 0.3500 Uiso R . . . 1 . H792 H 0.2010 0.6443 0.8937 0.2000 0.3500 Uiso R . . . 1 . H811 H 0.0166 0.5238 0.9084 0.1080 0.3500 Uiso R . . . 1 . H812 H -0.0861 0.5442 0.8469 0.1080 0.3500 Uiso R . . . 1 . H822 H -0.1244 0.3963 0.8481 0.1281 0.3500 Uiso R . . . 1 . H821 H -0.0852 0.4122 0.7808 0.1280 0.3500 Uiso R . . . 1 . H851 H -0.0391 0.3230 0.7172 0.0718 1.0000 Uiso R . . . . . H861 H 0.0400 0.2267 0.6537 0.0611 1.0000 Uiso R . . . . . H881 H 0.2958 0.2129 0.8251 0.0706 1.0000 Uiso R . . . . . H891 H 0.2233 0.3109 0.8886 0.0744 1.0000 Uiso R . . . . . H911 H 0.0986 0.1008 0.6116 0.0516 1.0000 Uiso R . . . . . H912 H 0.1846 0.1818 0.6030 0.0516 1.0000 Uiso R . . . . . H921 H 0.2735 0.0354 0.6297 0.0509 1.0000 Uiso R . . . . . H922 H 0.3498 0.1201 0.6154 0.0517 1.0000 Uiso R . . . . . H961 H 0.3009 0.1349 0.4822 0.0454 1.0000 Uiso R . . . . . H1011 H 0.4088 0.2918 0.0494 0.2393 1.0000 Uiso R . . . . . H1012 H 0.5071 0.2626 0.0140 0.2391 1.0000 Uiso R . . . . . H1013 H 0.4094 0.3115 -0.0252 0.2392 1.0000 Uiso R . . . . . H1021 H 0.6163 0.3750 0.0888 0.1431 1.0000 Uiso R . . . . . H1022 H 0.5060 0.4276 0.0658 0.1438 1.0000 Uiso R . . . . . H1042 H 0.6591 0.5313 0.0399 0.1848 1.0000 Uiso R . . . . . H1041 H 0.7574 0.4740 0.0670 0.1854 1.0000 Uiso R . . . . . H1051 H 0.8466 0.5104 -0.0111 0.2301 1.0000 Uiso R . . . . . H1052 H 0.7370 0.5607 -0.0435 0.2301 1.0000 Uiso R . . . . . H1053 H 0.7211 0.4585 -0.0702 0.2300 1.0000 Uiso R . . . . . H1732 H 0.3550 0.6647 0.5993 0.0832 0.6500 Uiso R . . . 2 . H1731 H 0.3116 0.5709 0.6098 0.0829 0.6500 Uiso R . . . 2 . H1741 H 0.1871 0.7012 0.6414 0.1119 0.6500 Uiso R . . . 2 . H1742 H 0.1588 0.6103 0.6611 0.1116 0.6500 Uiso R . . . 2 . H1761 H 0.3671 0.6495 0.8141 0.1381 0.6500 Uiso R . . . 2 . H1762 H 0.2582 0.5831 0.7556 0.1380 0.6500 Uiso R . . . 2 . H1771 H 0.2020 0.7249 0.8262 0.1339 0.6500 Uiso R . . . 2 . H1781 H 0.1181 0.5476 0.7850 0.1247 0.6500 Uiso R . . . 2 . H1791 H 0.0173 0.6672 0.8538 0.1111 0.6500 Uiso R . . . 2 . H1792 H -0.0660 0.5894 0.7961 0.1111 0.6500 Uiso R . . . 2 . H1812 H -0.1010 0.4667 0.9021 0.1443 0.6500 Uiso R . . . 2 . H1811 H -0.1610 0.5071 0.8368 0.1443 0.6500 Uiso R . . . 2 . H1821 H -0.1299 0.3708 0.7974 0.1273 0.6500 Uiso R . . . 2 . H1822 H -0.0400 0.4422 0.7770 0.1270 0.6500 Uiso R . . . 2 . H1701 H 0.0477 0.5475 0.4179 0.0706 0.6500 Uiso R . . . 2 . H1681 H 0.4063 0.5785 0.5243 0.0632 0.6500 Uiso R . . . 2 . H1711 H 0.0905 0.4810 0.3220 0.0646 0.6500 Uiso R . . . 2 . H1671 H 0.4477 0.5144 0.4286 0.0609 0.6500 Uiso R . . . 2 . H1641 H 0.4580 0.4963 0.3145 0.0520 0.6500 Uiso R . . . 2 . H1642 H 0.4416 0.4120 0.3419 0.0515 0.6500 Uiso R . . . 2 . H1631 H 0.4965 0.3992 0.2320 0.0846 0.6500 Uiso R . . . 2 . H1632 H 0.3555 0.4145 0.1936 0.0846 0.6500 Uiso R . . . 2 . H411 H 0.4342 0.7290 0.4324 0.0597 1.0000 Uiso R . . . . . H91 H 0.7489 0.6812 0.4579 0.0733 1.0000 Uiso R . . . . . C111 C 0.529(3) 1.0846(13) 1.0930(11) 0.1758 0.5000 Uani D U . 3 -1 . C112 C 0.529(4) 1.0633(8) 1.0183(13) 0.1316 0.5000 Uani D U . 3 -1 . O113 O 0.4885(11) 0.9755(4) 0.9924(5) 0.0984 0.5000 Uani D U . 3 -1 . C114 C 0.485(2) 0.9545(9) 0.9213(7) 0.1163 0.5000 Uani D U . 3 -1 . C115 C 0.437(2) 0.8609(9) 0.8972(9) 0.1455 0.5000 Uani D U . 3 -1 . H1111 H 0.5473 1.1443 1.1078 0.1704 0.5000 Uiso R . . 3 -1 . H1112 H 0.4600 1.0602 1.1067 0.1704 0.5000 Uiso R . . 3 -1 . H1113 H 0.5983 1.0619 1.1134 0.1704 0.5000 Uiso R . . 3 -1 . H1121 H 0.4602 1.0878 0.9995 0.1432 0.5000 Uiso R . . 3 -1 . H1122 H 0.5985 1.0895 1.0062 0.1432 0.5000 Uiso R . . 3 -1 . H1141 H 0.5671 0.9671 0.9190 0.1564 0.5000 Uiso R . . 3 -1 . H1142 H 0.4362 0.9858 0.8927 0.1564 0.5000 Uiso R . . 3 -1 . H1151 H 0.4410 0.8501 0.8509 0.1579 0.5000 Uiso R . . 3 -1 . H1152 H 0.4846 0.8278 0.9242 0.1579 0.5000 Uiso R . . 3 -1 . H1153 H 0.3536 0.8466 0.8978 0.1579 0.5000 Uiso R . . 3 -1 . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.071(2) 0.0409(18) 0.050(2) -0.0003(15) 0.0200(18) -0.0042(16) C2 0.069(3) 0.077(3) 0.051(2) -0.004(2) 0.0148(19) -0.015(2) C3 0.084(3) 0.072(3) 0.061(3) -0.013(2) 0.037(2) -0.019(2) C4 0.076(3) 0.051(2) 0.067(3) -0.0014(18) 0.037(2) -0.0113(19) C5 0.083(3) 0.0321(16) 0.072(3) 0.0123(16) 0.041(2) -0.0012(17) C6 0.079(3) 0.0368(17) 0.0475(19) 0.0099(14) 0.0221(18) 0.0094(16) O7 0.115(3) 0.0690(18) 0.100(2) 0.0324(17) 0.068(2) 0.0427(19) C8 0.085(3) 0.0439(19) 0.083(3) 0.027(2) 0.046(2) 0.0159(19) N9 0.070(2) 0.0518(18) 0.082(2) 0.0215(17) 0.0385(18) 0.0176(15) C10 0.062(2) 0.058(2) 0.097(3) 0.028(2) 0.035(2) 0.0197(19) C11 0.056(2) 0.057(2) 0.096(3) 0.039(2) 0.031(2) 0.0141(18) O12 0.0754(18) 0.0582(15) 0.0741(19) 0.0306(14) 0.0345(15) 0.0139(13) C13 0.052(2) 0.067(2) 0.073(3) 0.038(2) 0.0298(19) 0.0212(18) C14 0.051(2) 0.072(2) 0.062(2) 0.036(2) 0.0251(17) 0.0134(18) C15 0.050(2) 0.082(3) 0.060(2) 0.033(2) 0.0182(18) 0.0051(19) C16 0.048(2) 0.102(3) 0.0594(19) 0.0385(17) 0.0130(17) 0.011(2) C17 0.058(2) 0.096(3) 0.066(3) 0.051(2) 0.0270(19) 0.017(2) C18 0.054(2) 0.076(3) 0.081(3) 0.048(2) 0.028(2) 0.0177(19) O19 0.0666(18) 0.130(3) 0.0530(14) 0.0359(15) 0.0128(14) -0.0084(18) C20 0.077(3) 0.164(4) 0.058(2) 0.051(2) 0.015(2) 0.000(3) C21 0.083(4) 0.206(5) 0.050(2) 0.043(3) 0.003(2) -0.015(3) O22 0.090(3) 0.169(3) 0.0405(15) 0.0137(18) 0.0062(16) -0.035(2) C23 0.085(3) 0.232(6) 0.041(2) -0.011(3) 0.015(2) -0.043(3) C24 0.121(3) 0.172(4) 0.060(3) -0.030(4) 0.035(3) -0.080(3) O25 0.116(2) 0.114(2) 0.0521(17) 0.0020(18) 0.0181(18) -0.049(2) C26 0.200(4) 0.082(3) 0.078(4) -0.020(3) 0.049(4) -0.041(3) C27 0.190(4) 0.069(3) 0.054(2) -0.011(2) 0.030(3) 0.008(3) O28 0.180(3) 0.082(2) 0.0500(17) -0.0095(15) 0.027(2) 0.027(3) C29 0.163(3) 0.142(6) 0.066(3) -0.030(3) -0.011(3) 0.096(4) C30 0.206(7) 0.149(5) 0.062(3) -0.016(3) -0.017(4) 0.122(5) O31 0.093(2) 0.0787(18) 0.0395(13) -0.0032(12) 0.0073(13) 0.0231(16) C32 0.067(2) 0.065(2) 0.0355(15) 0.0031(15) 0.0073(15) 0.0218(19) C33 0.083(3) 0.063(2) 0.0373(18) 0.0155(16) 0.0166(17) 0.017(2) C34 0.072(2) 0.0488(19) 0.0424(19) 0.0110(15) 0.0130(17) 0.0097(17) C35 0.0522(19) 0.0481(18) 0.0371(17) 0.0114(14) 0.0093(14) 0.0168(15) C36 0.0490(18) 0.0467(17) 0.0370(16) 0.0093(13) 0.0082(14) 0.0165(14) C37 0.0526(19) 0.0494(19) 0.0446(19) 0.0048(15) 0.0043(15) 0.0146(15) O38 0.0595(14) 0.0429(12) 0.0355(12) 0.0073(9) 0.0107(10) 0.0081(10) C39 0.057(2) 0.0406(17) 0.0455(18) 0.0088(14) 0.0109(15) 0.0109(15) C40 0.058(2) 0.0448(18) 0.0443(19) 0.0074(14) 0.0025(15) 0.0107(15) N41 0.0621(18) 0.0448(15) 0.0388(15) 0.0056(12) 0.0044(13) 0.0146(13) C42 0.068(2) 0.0456(18) 0.0393(18) 0.0061(14) 0.0019(17) 0.0019(16) O43 0.0769(19) 0.0810(19) 0.0435(15) 0.0035(13) 0.0017(14) 0.0149(15) C51 0.104(3) 0.065(3) 0.039(2) -0.0087(18) 0.019(2) -0.033(2) N52 0.0584(17) 0.0506(16) 0.0326(14) 0.0035(12) 0.0082(12) -0.0138(13) C53 0.057(2) 0.059(2) 0.0321(16) 0.0103(15) 0.0094(14) -0.0064(16) C54 0.0422(17) 0.0468(17) 0.0342(16) 0.0111(13) 0.0060(13) -0.0020(13) C55 0.0379(15) 0.0395(15) 0.0350(16) 0.0103(12) 0.0057(12) 0.0031(12) C56 0.0349(15) 0.0429(16) 0.0349(16) 0.0113(13) 0.0060(12) 0.0035(12) C57 0.0484(18) 0.0482(18) 0.0371(17) 0.0091(14) 0.0086(14) -0.0052(14) C58 0.0452(17) 0.0520(18) 0.0360(16) 0.0157(14) 0.0071(13) -0.0002(14) C59 0.0467(18) 0.0465(17) 0.0433(17) 0.0178(14) 0.0138(14) 0.0037(14) N60 0.119(3) 0.068(2) 0.0362(17) 0.0154(15) 0.0159(18) -0.023(2) N61 0.129(3) 0.070(2) 0.0482(16) 0.0226(14) 0.023(2) -0.024(2) N62 0.0564(17) 0.0538(15) 0.0491(14) 0.0216(11) 0.0164(13) -0.0013(13) C63 0.060(7) 0.053(4) 0.057(8) 0.030(4) 0.017(6) -0.001(5) C64 0.077(7) 0.070(5) 0.076(7) 0.029(6) 0.028(5) 0.018(5) O65 0.079(5) 0.076(6) 0.074(5) 0.023(4) 0.029(4) 0.016(5) C66 0.056(5) 0.043(6) 0.073(5) 0.027(5) 0.022(4) 0.004(5) C67 0.064(7) 0.074(9) 0.067(7) 0.036(6) 0.019(5) 0.025(8) C68 0.042(5) 0.059(9) 0.078(7) 0.023(6) 0.014(6) 0.015(5) C69 0.037(5) 0.027(6) 0.123(6) 0.026(6) 0.021(5) 0.008(5) C70 0.042(6) 0.039(7) 0.115(7) 0.024(6) 0.022(5) 0.017(6) C71 0.060(6) 0.039(6) 0.114(7) 0.026(6) 0.031(6) 0.010(5) O72 0.022(5) 0.035(5) 0.130(6) 0.017(5) 0.013(4) 0.019(3) C73 0.041(6) 0.018(9) 0.139(7) 0.003(6) -0.012(6) 0.003(5) C74 0.025(6) 0.044(8) 0.113(6) 0.033(7) 0.002(5) 0.001(5) O75 0.025(4) 0.093(6) 0.102(6) 0.017(5) 0.007(3) 0.005(4) C76 0.147(14) 0.096(12) 0.068(8) -0.010(7) 0.017(7) -0.025(9) C77 0.125(12) 0.25(2) 0.098(12) 0.009(13) 0.021(10) 0.096(14) C78 0.140(16) 0.128(13) 0.140(16) 0.025(12) 0.047(14) -0.022(13) C79 0.23(2) 0.152(11) 0.087(12) 0.024(11) 0.009(12) -0.047(15) O80 0.219(13) 0.105(6) 0.082(7) 0.057(6) 0.090(8) 0.061(7) C81 0.072(9) 0.103(6) 0.081(10) 0.013(8) -0.004(6) 0.023(6) C82 0.055(8) 0.142(8) 0.111(11) -0.095(8) 0.041(6) -0.009(5) O83 0.109(3) 0.0680(19) 0.082(2) -0.0219(16) 0.044(2) -0.0056(16) C84 0.075(3) 0.0468(19) 0.070(3) -0.0012(17) 0.036(2) -0.0077(18) C85 0.066(2) 0.050(2) 0.064(2) 0.0041(17) 0.0260(19) -0.0006(17) C86 0.056(2) 0.0494(19) 0.0479(19) 0.0065(15) 0.0167(16) -0.0031(16) C87 0.055(2) 0.0455(17) 0.0426(18) 0.0093(14) 0.0187(15) -0.0045(15) C88 0.063(2) 0.060(2) 0.0423(19) 0.0083(16) 0.0144(16) -0.0054(17) C89 0.082(3) 0.059(2) 0.0422(19) -0.0054(17) 0.0245(19) -0.0188(19) O90 0.0551(14) 0.0622(14) 0.0349(12) 0.0089(10) 0.0109(10) 0.0101(11) C91 0.0443(17) 0.0501(18) 0.0348(16) 0.0093(14) 0.0087(13) 0.0010(14) C92 0.0468(17) 0.0530(18) 0.0339(16) 0.0147(14) 0.0100(13) 0.0067(14) N93 0.0395(13) 0.0426(14) 0.0348(13) 0.0128(11) 0.0108(11) 0.0047(11) N94 0.0477(15) 0.0435(14) 0.0391(15) 0.0128(11) 0.0123(12) 0.0008(12) N95 0.0448(14) 0.0417(14) 0.0380(14) 0.0135(11) 0.0108(11) 0.0032(11) C96 0.0424(16) 0.0410(16) 0.0357(16) 0.0129(13) 0.0096(13) 0.0020(13) C97 0.0349(15) 0.0396(15) 0.0350(15) 0.0123(12) 0.0079(12) 0.0053(12) C101 0.172(9) 0.208(10) 0.142(8) 0.006(6) 0.053(7) -0.045(7) C102 0.116(5) 0.146(6) 0.124(5) 0.037(5) 0.010(4) 0.021(4) O103 0.116(3) 0.101(3) 0.113(3) 0.007(2) 0.009(2) 0.011(2) C104 0.188(9) 0.124(6) 0.152(7) 0.039(5) -0.009(5) -0.037(5) C105 0.164(8) 0.113(6) 0.188(8) 0.047(6) 0.014(6) -0.012(5) Cl1 0.0517(5) 0.0428(4) 0.0456(4) 0.0118(3) 0.0099(3) 0.0044(3) C173 0.047(5) 0.027(7) 0.121(4) 0.018(4) -0.011(3) 0.009(3) C174 0.058(5) 0.135(9) 0.096(4) 0.038(5) 0.001(3) 0.001(5) O175 0.043(3) 0.179(7) 0.115(4) 0.067(4) -0.012(3) -0.007(4) C176 0.186(9) 0.131(8) 0.051(4) -0.005(5) 0.039(6) 0.005(7) C177 0.070(5) 0.255(13) 0.070(5) 0.046(7) -0.028(3) 0.043(5) C178 0.104(6) 0.164(9) 0.080(6) -0.027(6) 0.004(4) 0.062(5) C179 0.113(5) 0.126(6) 0.045(4) 0.010(3) 0.007(3) 0.062(5) O180 0.183(8) 0.102(5) 0.118(6) 0.036(4) -0.002(5) 0.016(5) C181 0.156(9) 0.089(6) 0.138(9) -0.019(5) 0.017(7) 0.036(4) C182 0.110(9) 0.124(7) 0.079(6) 0.004(5) 0.017(5) 0.046(6) O172 0.039(4) 0.077(5) 0.102(3) 0.013(3) 0.005(2) 0.012(3) C169 0.043(3) 0.040(5) 0.093(3) 0.025(3) 0.005(3) 0.003(3) C170 0.044(4) 0.050(4) 0.090(4) 0.015(3) 0.011(3) 0.010(3) C168 0.041(2) 0.043(3) 0.058(3) 0.009(3) -0.003(3) -0.002(2) C171 0.035(2) 0.045(4) 0.077(3) 0.020(3) 0.003(3) 0.003(2) C166 0.037(3) 0.039(3) 0.051(3) 0.014(2) -0.003(2) 0.002(3) C167 0.036(3) 0.044(4) 0.055(3) 0.015(3) -0.003(2) -0.003(2) O165 0.0323(16) 0.054(2) 0.055(2) 0.0150(17) -0.0007(16) 0.0041(16) C164 0.0342(19) 0.039(2) 0.065(3) 0.021(2) 0.008(2) -0.0003(19) C163 0.046(3) 0.053(3) 0.060(4) 0.033(3) 0.017(3) 0.005(3) C111 0.26(3) 0.085(12) 0.149(12) 0.010(12) 0.051(17) -0.025(19) C112 0.181(17) 0.063(13) 0.132(9) 0.046(9) 0.019(12) -0.005(15) O113 0.130(10) 0.062(13) 0.107(7) 0.049(9) 0.037(9) -0.003(15) C114 0.149(14) 0.104(9) 0.118(9) 0.052(8) 0.058(11) 0.033(10) C115 0.22(2) 0.117(11) 0.102(10) 0.028(8) 0.061(12) 0.001(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.62(4) 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 C1 . C2 . 1.397(6) yes C1 . C6 . 1.378(6) yes C1 . C42 . 1.513(6) yes C2 . C3 . 1.393(7) yes C2 . H21 . 0.931 no C3 . C4 . 1.351(7) yes C3 . H31 . 0.915 no C4 . C5 . 1.388(6) yes C4 . H41 . 0.934 no C5 . C6 . 1.404(6) yes C5 . C8 . 1.489(6) yes C6 . H61 . 0.927 no O7 . C8 . 1.230(5) yes C8 . N9 . 1.337(6) yes N9 . C10 . 1.460(6) yes N9 . H91 . 0.858 no C10 . C11 . 1.487(7) yes C10 . H102 . 0.989 no C10 . H101 . 0.971 no C11 . O12 . 1.442(5) yes C11 . H111 . 0.989 no C11 . H112 . 0.976 no O12 . C13 . 1.363(5) yes C13 . C14 . 1.398(6) yes C13 . C18 . 1.391(5) yes C14 . C15 . 1.361(6) yes C14 . H141 . 0.906 no C15 . C16 . 1.397(5) yes C15 . H151 . 0.931 no C16 . C17 . 1.377(7) yes C16 . O19 . 1.374(6) yes C17 . C18 . 1.378(7) yes C17 . H171 . 0.923 no C18 . H181 . 0.945 no O19 . C20 . 1.429(5) yes C20 . C21 . 1.486(9) yes C20 . H201 . 0.976 no C20 . H202 . 0.982 no C21 . O22 . 1.439(9) yes C21 . H212 . 0.964 no C21 . H211 . 0.974 no O22 . C23 . 1.412(8) yes C23 . C24 . 1.461(12) yes C23 . H231 . 0.980 no C23 . H232 . 0.973 no C24 . O25 . 1.419(9) yes C24 . H241 . 0.909 no O25 . C26 . 1.427(10) yes C26 . C27 . 1.465(11) yes C26 . H261 . 0.992 no C26 . H262 . 0.978 no C27 . O28 . 1.419(6) yes C27 . H272 . 0.969 no C27 . H271 . 0.982 no O28 . C29 . 1.422(9) yes C29 . C30 . 1.519(7) yes C29 . H292 . 0.977 no C29 . H291 . 0.971 no C30 . O31 . 1.373(7) yes C30 . H301 . 0.980 no C30 . H302 . 1.000 no O31 . C32 . 1.389(4) yes C32 . C33 . 1.371(6) yes C32 . C37 . 1.397(6) yes C33 . C34 . 1.378(5) yes C33 . H331 . 0.923 no C34 . C35 . 1.395(5) yes C34 . H341 . 0.935 no C35 . C36 . 1.390(5) yes C35 . O38 . 1.367(4) yes C36 . C37 . 1.380(5) yes C36 . H361 . 0.939 no C37 . H371 . 0.922 no O38 . C39 . 1.432(4) yes C39 . C40 . 1.505(5) yes C39 . H392 . 0.957 no C39 . H391 . 0.983 no C40 . N41 . 1.454(5) yes C40 . H401 . 0.972 no C40 . H402 . 0.974 no N41 . C42 . 1.345(5) yes N41 . H411 . 0.868 no C42 . O43 . 1.231(5) yes C51 . N52 . 1.486(5) yes C51 . H511 . 0.948 no C51 . H512 . 0.948 no C51 . H513 . 0.951 no N52 . C53 . 1.335(4) yes N52 . C57 . 1.345(4) yes C53 . C54 . 1.380(5) yes C53 . H531 . 0.934 no C54 . C55 . 1.383(4) yes C54 . C58 . 1.469(4) yes C55 . C56 . 1.394(4) yes C55 . H551 . 0.960 no C56 . C57 . 1.380(5) yes C56 . C97 . 1.457(4) yes C57 . H571 . 0.927 no C58 . C59 . 1.360(5) yes C58 . N60 . 1.348(5) yes C59 . N62 . 1.340(4) yes C59 . H591 . 0.940 no N60 . N61 . 1.314(5) yes N61 . N62 . 1.325(5) yes N62 . C63 . 1.480(9) yes C63 . C64 . 1.511(9) yes C63 . H631 . 0.986 no C63 . H632 . 0.990 no C64 . O65 . 1.426(9) yes C64 . H642 . 0.971 no C64 . H641 . 0.981 no O65 . C66 . 1.407(13) yes C66 . C67 . 1.403(9) yes C66 . C71 . 1.402(9) yes C67 . C68 . 1.391(9) yes C67 . H671 . 0.938 no C68 . C69 . 1.396(9) yes C68 . H681 . 0.928 no C69 . C70 . 1.407(9) yes C69 . O72 . 1.471(13) yes C70 . C71 . 1.401(10) yes C70 . H701 . 0.938 no C71 . H711 . 0.927 no O72 . C73 . 1.365(9) yes C73 . C74 . 1.478(9) yes C73 . H732 . 0.975 no C73 . H731 . 0.978 no C74 . O75 . 1.398(9) yes C74 . H741 . 0.972 no C74 . H742 . 0.977 no O75 . C76 . 1.366(9) yes C76 . C77 . 1.512(10) yes C76 . H761 . 0.979 no C76 . H762 . 0.976 no C77 . C78 . 1.362(10) yes C77 . H771 . 0.930 no C78 . C79 . 1.546(10) yes C78 . H781 . 0.937 no C79 . O80 . 1.425(10) yes C79 . H791 . 0.967 no C79 . H792 . 0.967 no O80 . C81 . 1.414(10) yes C81 . C82 . 1.533(10) yes C81 . H811 . 0.973 no C81 . H812 . 0.969 no C82 . O83 . 1.423(9) yes C82 . H822 . 0.966 no C82 . H821 . 0.971 no O83 . C84 . 1.400(5) yes C84 . C85 . 1.373(6) yes C84 . C89 . 1.385(7) yes C85 . C86 . 1.399(6) yes C85 . H851 . 0.948 no C86 . C87 . 1.381(5) yes C86 . H861 . 0.935 no C87 . C88 . 1.378(5) yes C87 . O90 . 1.379(4) yes C88 . C89 . 1.383(6) yes C88 . H881 . 0.930 no C89 . H891 . 0.931 no O90 . C91 . 1.420(4) yes C91 . C92 . 1.507(5) yes C91 . H911 . 0.957 no C91 . H912 . 0.984 no C92 . N93 . 1.455(4) yes C92 . H921 . 0.963 no C92 . H922 . 0.979 no N93 . N94 . 1.345(4) yes N93 . C96 . 1.341(4) yes N94 . N95 . 1.302(4) yes N95 . C97 . 1.361(4) yes C96 . C97 . 1.368(4) yes C96 . H961 . 0.923 no C101 . C102 . 1.484(8) yes C101 . H1011 . 0.969 no C101 . H1012 . 0.965 no C101 . H1013 . 0.958 no C102 . O103 . 1.450(9) yes C102 . H1021 . 0.994 no C102 . H1022 . 0.993 no O103 . C104 . 1.394(9) yes C104 . C105 . 1.515(8) yes C104 . H1042 . 0.981 no C104 . H1041 . 0.973 no C105 . H1051 . 1.010 no C105 . H1052 . 0.996 no C105 . H1053 . 1.000 no C173 . C174 . 1.562(8) yes C173 . O172 . 1.448(11) yes C173 . H1732 . 0.974 no C173 . H1731 . 0.980 no C174 . O175 . 1.531(8) yes C174 . H1741 . 0.982 no C174 . H1742 . 0.973 no O175 . C176 . 1.417(8) yes C176 . C177 . 1.456(9) yes C176 . H1761 . 0.990 no C176 . H1762 . 0.973 no C177 . C178 . 1.320(9) yes C177 . H1771 . 0.931 no C178 . C179 . 1.462(8) yes C178 . H1781 . 0.953 no C179 . O180 . 1.397(8) yes C179 . H1791 . 0.965 no C179 . H1792 . 0.965 no O180 . C181 . 1.393(8) yes C181 . C182 . 1.514(8) yes C181 . H1812 . 0.974 no C181 . H1811 . 0.982 no C182 . H1821 . 0.965 no C182 . H1822 . 0.971 no O172 . C169 . 1.338(10) yes C169 . C170 . 1.402(8) yes C169 . C168 . 1.411(7) yes C170 . C171 . 1.386(8) yes C170 . H1701 . 0.953 no C168 . C167 . 1.388(8) yes C168 . H1681 . 0.930 no C171 . C166 . 1.395(7) yes C171 . H1711 . 0.931 no C166 . C167 . 1.387(7) yes C166 . O165 . 1.396(7) yes C167 . H1671 . 0.939 no O165 . C164 . 1.417(5) yes C164 . C163 . 1.526(8) yes C164 . H1641 . 0.952 no C164 . H1642 . 0.958 no C163 . H1631 . 1.035 no C163 . H1632 . 1.031 no C111 . C112 . 1.514(10) yes C111 . H1111 . 0.950 no C111 . H1112 . 0.950 no C111 . H1113 . 0.950 no C112 . O113 . 1.413(9) yes C112 . H1121 . 0.950 no C112 . H1122 . 0.950 no O113 . C114 . 1.432(9) yes C114 . C115 . 1.501(9) yes C114 . H1141 . 0.950 no C114 . H1142 . 0.950 no C115 . H1151 . 0.950 no C115 . H1152 . 0.950 no C115 . H1153 . 0.950 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 C2 . C1 . C6 . 118.4(4) yes C2 . C1 . C42 . 117.9(4) yes C6 . C1 . C42 . 123.7(3) yes C1 . C2 . C3 . 119.7(5) yes C1 . C2 . H21 . 117.1 no C3 . C2 . H21 . 123.2 no C2 . C3 . C4 . 121.6(4) yes C2 . C3 . H31 . 119.7 no C4 . C3 . H31 . 118.7 no C3 . C4 . C5 . 120.0(4) yes C3 . C4 . H41 . 120.1 no C5 . C4 . H41 . 119.9 no C4 . C5 . C6 . 119.0(4) yes C4 . C5 . C8 . 117.5(4) yes C6 . C5 . C8 . 123.5(4) yes C5 . C6 . C1 . 121.4(4) yes C5 . C6 . H61 . 120.2 no C1 . C6 . H61 . 118.4 no C5 . C8 . O7 . 121.0(4) yes C5 . C8 . N9 . 117.4(4) yes O7 . C8 . N9 . 121.6(4) yes C8 . N9 . C10 . 119.7(4) yes C8 . N9 . H91 . 120.3 no C10 . N9 . H91 . 119.9 no N9 . C10 . C11 . 111.4(3) yes N9 . C10 . H102 . 109.8 no C11 . C10 . H102 . 107.6 no N9 . C10 . H101 . 108.8 no C11 . C10 . H101 . 109.8 no H102 . C10 . H101 . 109.4 no C10 . C11 . O12 . 107.9(3) yes C10 . C11 . H111 . 112.2 no O12 . C11 . H111 . 108.8 no C10 . C11 . H112 . 110.0 no O12 . C11 . H112 . 108.4 no H111 . C11 . H112 . 109.5 no C11 . O12 . C13 . 116.3(3) yes O12 . C13 . C14 . 116.2(3) yes O12 . C13 . C18 . 125.2(4) yes C14 . C13 . C18 . 118.7(4) yes C13 . C14 . C15 . 120.7(3) yes C13 . C14 . H141 . 119.8 no C15 . C14 . H141 . 119.5 no C14 . C15 . C16 . 120.4(4) yes C14 . C15 . H151 . 119.2 no C16 . C15 . H151 . 120.3 no C15 . C16 . C17 . 119.3(4) yes C15 . C16 . O19 . 115.9(4) yes C17 . C16 . O19 . 124.8(4) yes C16 . C17 . C18 . 120.5(4) yes C16 . C17 . H171 . 120.3 no C18 . C17 . H171 . 119.2 no C13 . C18 . C17 . 120.5(4) yes C13 . C18 . H181 . 119.9 no C17 . C18 . H181 . 119.6 no C16 . O19 . C20 . 116.9(4) yes O19 . C20 . C21 . 108.8(5) yes O19 . C20 . H201 . 107.3 no C21 . C20 . H201 . 109.4 no O19 . C20 . H202 . 109.3 no C21 . C20 . H202 . 110.8 no H201 . C20 . H202 . 111.2 no C20 . C21 . O22 . 109.9(5) yes C20 . C21 . H212 . 109.3 no O22 . C21 . H212 . 107.4 no C20 . C21 . H211 . 111.8 no O22 . C21 . H211 . 111.8 no H212 . C21 . H211 . 106.5 no C21 . O22 . C23 . 111.1(5) yes O22 . C23 . C24 . 111.4(6) yes O22 . C23 . H231 . 107.9 no C24 . C23 . H231 . 110.4 no O22 . C23 . H232 . 108.8 no C24 . C23 . H232 . 107.6 no H231 . C23 . H232 . 110.8 no C23 . C24 . O25 . 111.2(6) yes C23 . C24 . H241 . 124.9 no O25 . C24 . H241 . 123.8 no C24 . O25 . C26 . 112.9(6) yes O25 . C26 . C27 . 109.8(5) yes O25 . C26 . H261 . 107.8 no C27 . C26 . H261 . 108.8 no O25 . C26 . H262 . 109.4 no C27 . C26 . H262 . 109.9 no H261 . C26 . H262 . 111.2 no C26 . C27 . O28 . 108.2(6) yes C26 . C27 . H272 . 111.2 no O28 . C27 . H272 . 110.9 no C26 . C27 . H271 . 108.2 no O28 . C27 . H271 . 109.4 no H272 . C27 . H271 . 108.8 no C27 . O28 . C29 . 112.4(5) yes O28 . C29 . C30 . 106.9(6) yes O28 . C29 . H292 . 112.8 no C30 . C29 . H292 . 109.4 no O28 . C29 . H291 . 107.4 no C30 . C29 . H291 . 110.6 no H292 . C29 . H291 . 109.8 no C29 . C30 . O31 . 108.8(5) yes C29 . C30 . H301 . 109.2 no O31 . C30 . H301 . 109.1 no C29 . C30 . H302 . 111.2 no O31 . C30 . H302 . 107.8 no H301 . C30 . H302 . 110.7 no C30 . O31 . C32 . 114.3(4) yes O31 . C32 . C33 . 118.9(4) yes O31 . C32 . C37 . 121.6(4) yes C33 . C32 . C37 . 119.5(3) yes C32 . C33 . C34 . 121.3(4) yes C32 . C33 . H331 . 119.7 no C34 . C33 . H331 . 119.0 no C33 . C34 . C35 . 119.6(4) yes C33 . C34 . H341 . 121.0 no C35 . C34 . H341 . 119.4 no C34 . C35 . C36 . 119.4(3) yes C34 . C35 . O38 . 124.5(3) yes C36 . C35 . O38 . 116.2(3) yes C35 . C36 . C37 . 120.5(3) yes C35 . C36 . H361 . 118.7 no C37 . C36 . H361 . 120.8 no C32 . C37 . C36 . 119.8(3) yes C32 . C37 . H371 . 119.4 no C36 . C37 . H371 . 120.8 no C35 . O38 . C39 . 117.0(3) yes O38 . C39 . C40 . 108.4(3) yes O38 . C39 . H392 . 109.2 no C40 . C39 . H392 . 111.1 no O38 . C39 . H391 . 109.7 no C40 . C39 . H391 . 109.5 no H392 . C39 . H391 . 108.9 no C39 . C40 . N41 . 112.5(3) yes C39 . C40 . H401 . 106.6 no N41 . C40 . H401 . 108.7 no C39 . C40 . H402 . 108.8 no N41 . C40 . H402 . 110.3 no H401 . C40 . H402 . 109.9 no C40 . N41 . C42 . 119.8(3) yes C40 . N41 . H411 . 119.4 no C42 . N41 . H411 . 119.2 no C1 . C42 . N41 . 118.8(3) yes C1 . C42 . O43 . 120.2(3) yes N41 . C42 . O43 . 120.9(4) yes N52 . C51 . H511 . 110.5 no N52 . C51 . H512 . 109.8 no H511 . C51 . H512 . 107.8 no N52 . C51 . H513 . 110.3 no H511 . C51 . H513 . 108.5 no H512 . C51 . H513 . 110.0 no C51 . N52 . C53 . 120.2(3) yes C51 . N52 . C57 . 118.0(3) yes C53 . N52 . C57 . 121.8(3) yes N52 . C53 . C54 . 120.6(3) yes N52 . C53 . H531 . 119.6 no C54 . C53 . H531 . 119.8 no C53 . C54 . C55 . 118.5(3) yes C53 . C54 . C58 . 120.6(3) yes C55 . C54 . C58 . 120.8(3) yes C54 . C55 . C56 . 120.4(3) yes C54 . C55 . H551 . 120.2 no C56 . C55 . H551 . 119.4 no C55 . C56 . C57 . 118.3(3) yes C55 . C56 . C97 . 121.6(3) yes C57 . C56 . C97 . 120.0(3) yes C56 . C57 . N52 . 120.4(3) yes C56 . C57 . H571 . 121.1 no N52 . C57 . H571 . 118.5 no C54 . C58 . C59 . 129.5(3) yes C54 . C58 . N60 . 122.2(3) yes C59 . C58 . N60 . 108.3(3) yes C58 . C59 . N62 . 104.9(3) yes C58 . C59 . H591 . 128.3 no N62 . C59 . H591 . 126.8 no C58 . N60 . N61 . 108.6(3) yes N60 . N61 . N62 . 107.5(3) yes C59 . N62 . N61 . 110.8(3) yes C59 . N62 . C63 . 120.7(8) yes N61 . N62 . C63 . 128.4(8) yes N62 . C63 . C64 . 108.2(7) yes N62 . C63 . H631 . 105.3 no C64 . C63 . H631 . 104.4 no N62 . C63 . H632 . 114.8 no C64 . C63 . H632 . 114.7 no H631 . C63 . H632 . 108.6 no C63 . C64 . O65 . 109.0(7) yes C63 . C64 . H642 . 110.7 no O65 . C64 . H642 . 109.1 no C63 . C64 . H641 . 106.1 no O65 . C64 . H641 . 112.5 no H642 . C64 . H641 . 109.4 no C64 . O65 . C66 . 115.7(7) yes O65 . C66 . C67 . 127.2(10) yes O65 . C66 . C71 . 115.8(11) yes C67 . C66 . C71 . 116.8(13) yes C66 . C67 . C68 . 120.9(12) yes C66 . C67 . H671 . 118.6 no C68 . C67 . H671 . 120.5 no C67 . C68 . C69 . 123.9(13) yes C67 . C68 . H681 . 117.6 no C69 . C68 . H681 . 118.5 no C68 . C69 . C70 . 114.4(13) yes C68 . C69 . O72 . 125.2(12) yes C70 . C69 . O72 . 120.4(10) yes C69 . C70 . C71 . 123.0(14) yes C69 . C70 . H701 . 117.2 no C71 . C70 . H701 . 119.8 no C66 . C71 . C70 . 121.0(14) yes C66 . C71 . H711 . 119.4 no C70 . C71 . H711 . 119.6 no C69 . O72 . C73 . 116.6(9) yes O72 . C73 . C74 . 99.9(7) yes O72 . C73 . H732 . 99.1 no C74 . C73 . H732 . 103.4 no O72 . C73 . H731 . 121.1 no C74 . C73 . H731 . 120.5 no H732 . C73 . H731 . 109.6 no C73 . C74 . O75 . 104.4(7) yes C73 . C74 . H741 . 118.3 no O75 . C74 . H741 . 111.5 no C73 . C74 . H742 . 101.8 no O75 . C74 . H742 . 111.6 no H741 . C74 . H742 . 108.7 no C74 . O75 . C76 . 101.8(8) yes O75 . C76 . C77 . 109.8(9) yes O75 . C76 . H761 . 112.0 no C77 . C76 . H761 . 104.3 no O75 . C76 . H762 . 110.6 no C77 . C76 . H762 . 109.8 no H761 . C76 . H762 . 110.1 no C76 . C77 . C78 . 121.7(10) yes C76 . C77 . H771 . 119.0 no C78 . C77 . H771 . 119.0 no C77 . C78 . C79 . 127.7(10) yes C77 . C78 . H781 . 119.7 no C79 . C78 . H781 . 112.4 no C78 . C79 . O80 . 108.5(8) yes C78 . C79 . H791 . 116.5 no O80 . C79 . H791 . 107.8 no C78 . C79 . H792 . 106.4 no O80 . C79 . H792 . 107.4 no H791 . C79 . H792 . 109.8 no C79 . O80 . C81 . 114.2(8) yes O80 . C81 . C82 . 110.3(8) yes O80 . C81 . H811 . 108.8 no C82 . C81 . H811 . 107.1 no O80 . C81 . H812 . 110.6 no C82 . C81 . H812 . 110.0 no H811 . C81 . H812 . 110.0 no C81 . C82 . O83 . 106.7(7) yes C81 . C82 . H822 . 111.6 no O83 . C82 . H822 . 111.5 no C81 . C82 . H821 . 108.5 no O83 . C82 . H821 . 108.5 no H822 . C82 . H821 . 109.9 no C82 . O83 . C84 . 125.4(7) yes O83 . C84 . C85 . 124.0(5) yes O83 . C84 . C89 . 116.1(4) yes C85 . C84 . C89 . 119.9(4) yes C84 . C85 . C86 . 119.5(4) yes C84 . C85 . H851 . 120.5 no C86 . C85 . H851 . 119.9 no C85 . C86 . C87 . 120.3(4) yes C85 . C86 . H861 . 120.4 no C87 . C86 . H861 . 119.3 no C86 . C87 . C88 . 119.8(4) yes C86 . C87 . O90 . 124.3(3) yes C88 . C87 . O90 . 115.9(3) yes C87 . C88 . C89 . 119.9(4) yes C87 . C88 . H881 . 119.2 no C89 . C88 . H881 . 120.9 no C84 . C89 . C88 . 120.5(4) yes C84 . C89 . H891 . 120.2 no C88 . C89 . H891 . 119.3 no C87 . O90 . C91 . 117.8(3) yes O90 . C91 . C92 . 104.6(3) yes O90 . C91 . H911 . 113.9 no C92 . C91 . H911 . 111.4 no O90 . C91 . H912 . 112.9 no C92 . C91 . H912 . 105.8 no H911 . C91 . H912 . 107.9 no C91 . C92 . N93 . 112.4(3) yes C91 . C92 . H921 . 109.3 no N93 . C92 . H921 . 106.8 no C91 . C92 . H922 . 108.7 no N93 . C92 . H922 . 108.0 no H921 . C92 . H922 . 111.7 no C92 . N93 . N94 . 120.6(2) yes C92 . N93 . C96 . 128.5(3) yes N94 . N93 . C96 . 110.9(3) yes N93 . N94 . N95 . 107.5(2) yes N94 . N95 . C97 . 108.6(2) yes N93 . C96 . C97 . 104.5(3) yes N93 . C96 . H961 . 127.4 no C97 . C96 . H961 . 128.1 no C56 . C97 . C96 . 129.1(3) yes C56 . C97 . N95 . 122.4(3) yes C96 . C97 . N95 . 108.5(3) yes C102 . C101 . H1011 . 110.3 no C102 . C101 . H1012 . 104.9 no H1011 . C101 . H1012 . 110.4 no C102 . C101 . H1013 . 108.4 no H1011 . C101 . H1013 . 111.6 no H1012 . C101 . H1013 . 111.0 no C101 . C102 . O103 . 109.0(7) yes C101 . C102 . H1021 . 109.4 no O103 . C102 . H1021 . 108.9 no C101 . C102 . H1022 . 107.2 no O103 . C102 . H1022 . 110.8 no H1021 . C102 . H1022 . 111.5 no C102 . O103 . C104 . 109.9(6) yes O103 . C104 . C105 . 106.2(7) yes O103 . C104 . H1042 . 108.0 no C105 . C104 . H1042 . 108.4 no O103 . C104 . H1041 . 109.9 no C105 . C104 . H1041 . 113.1 no H1042 . C104 . H1041 . 111.0 no C104 . C105 . H1051 . 106.8 no C104 . C105 . H1052 . 110.9 no H1051 . C105 . H1052 . 110.7 no C104 . C105 . H1053 . 108.2 no H1051 . C105 . H1053 . 109.2 no H1052 . C105 . H1053 . 111.0 no C174 . C173 . O172 . 104.6(6) yes C174 . C173 . H1732 . 111.5 no O172 . C173 . H1732 . 113.9 no C174 . C173 . H1731 . 107.6 no O172 . C173 . H1731 . 110.7 no H1732 . C173 . H1731 . 108.2 no C173 . C174 . O175 . 113.1(6) yes C173 . C174 . H1741 . 106.0 no O175 . C174 . H1741 . 105.5 no C173 . C174 . H1742 . 113.0 no O175 . C174 . H1742 . 110.6 no H1741 . C174 . H1742 . 108.1 no C174 . O175 . C176 . 108.8(6) yes O175 . C176 . C177 . 115.7(7) yes O175 . C176 . H1761 . 107.4 no C177 . C176 . H1761 . 106.1 no O175 . C176 . H1762 . 111.0 no C177 . C176 . H1762 . 105.9 no H1761 . C176 . H1762 . 110.7 no C176 . C177 . C178 . 110.1(8) yes C176 . C177 . H1771 . 123.4 no C178 . C177 . H1771 . 126.4 no C177 . C178 . C179 . 122.9(7) yes C177 . C178 . H1781 . 120.1 no C179 . C178 . H1781 . 117.0 no C178 . C179 . O180 . 108.2(7) yes C178 . C179 . H1791 . 108.5 no O180 . C179 . H1791 . 111.5 no C178 . C179 . H1792 . 108.3 no O180 . C179 . H1792 . 109.0 no H1791 . C179 . H1792 . 111.3 no C179 . O180 . C181 . 112.3(7) yes O180 . C181 . C182 . 109.7(8) yes O180 . C181 . H1812 . 108.1 no C182 . C181 . H1812 . 109.6 no O180 . C181 . H1811 . 108.1 no C182 . C181 . H1811 . 111.3 no H1812 . C181 . H1811 . 110.0 no C181 . C182 . O83 . 111.5(6) yes C181 . C182 . H1821 . 110.5 no O83 . C182 . H1821 . 108.7 no C181 . C182 . H1822 . 106.5 no O83 . C182 . H1822 . 109.1 no H1821 . C182 . H1822 . 110.6 no C173 . O172 . C169 . 110.2(7) yes O172 . C169 . C170 . 115.8(7) yes O172 . C169 . C168 . 128.0(7) yes C170 . C169 . C168 . 116.2(8) yes C169 . C170 . C171 . 121.9(8) yes C169 . C170 . H1701 . 118.5 no C171 . C170 . H1701 . 119.6 no C169 . C168 . C167 . 122.0(6) yes C169 . C168 . H1681 . 120.0 no C167 . C168 . H1681 . 118.0 no C170 . C171 . C166 . 120.9(6) yes C170 . C171 . H1711 . 119.3 no C166 . C171 . H1711 . 119.8 no C171 . C166 . C167 . 118.4(6) yes C171 . C166 . O165 . 115.7(5) yes C167 . C166 . O165 . 125.9(5) yes C168 . C167 . C166 . 120.6(6) yes C168 . C167 . H1671 . 119.5 no C166 . C167 . H1671 . 119.9 no C166 . O165 . C164 . 115.4(4) yes O165 . C164 . C163 . 108.8(4) yes O165 . C164 . H1641 . 109.3 no C163 . C164 . H1641 . 110.7 no O165 . C164 . H1642 . 108.7 no C163 . C164 . H1642 . 111.4 no H1641 . C164 . H1642 . 107.9 no C164 . C163 . N62 . 109.5(5) yes C164 . C163 . H1631 . 109.1 no N62 . C163 . H1631 . 107.1 no C164 . C163 . H1632 . 113.8 no N62 . C163 . H1632 . 108.6 no H1631 . C163 . H1632 . 108.5 no C112 . C111 . H1111 . 110.3 no C112 . C111 . H1112 . 119.2 no H1111 . C111 . H1112 . 109.5 no C112 . C111 . H1113 . 98.1 no H1111 . C111 . H1113 . 109.5 no H1112 . C111 . H1113 . 109.5 no C111 . C112 . O113 . 111.7(16) yes C111 . C112 . H1121 . 96.1 no O113 . C112 . H1121 . 105.3 no C111 . C112 . H1122 . 117.0 no O113 . C112 . H1122 . 114.9 no H1121 . C112 . H1122 . 109.5 no C112 . O113 . C114 . 112.4(12) yes O113 . C114 . C115 . 109.0(11) yes O113 . C114 . H1141 . 107.0 no C115 . C114 . H1141 . 107.8 no O113 . C114 . H1142 . 112.4 no C115 . C114 . H1142 . 111.0 no H1141 . C114 . H1142 . 109.5 no C114 . C115 . H1151 . 105.5 no C114 . C115 . H1152 . 113.0 no H1151 . C115 . H1152 . 109.5 no C114 . C115 . H1153 . 109.8 no H1151 . C115 . H1153 . 109.5 no H1152 . C115 . H1153 . 109.5 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 C36 . H361 . O38 2_676 169.59(9) 0.939 2.566 3.493(11) yes C51 . H512 . O28 2_666 161.95(15) 0.948 2.326 3.241(11) yes C51 . H513 . O22 2_666 141.91(13) 0.951 2.497 3.298(11) yes C164 . H631 . C59 . 120.8(10) 0.849 2.433 2.960(11) yes C63 . H632 . C76 2_666 130.5(5) 0.990 2.368 3.105(11) yes C163 . H632 . C76 2_666 145.6(14) 0.983 2.368 3.227(11) yes C64 . H642 . C2 . 152.0(3) 0.971 2.568 3.455(11) yes C70 . H701 . O7 1_455 153.5(3) 0.938 2.592 3.457(11) yes C170 . H701 . O7 1_455 171.1(10) 0.985 2.592 3.568(11) yes C71 . H711 . C178 2_566 167.7(3) 0.927 2.450 3.362(11) yes C76 . H761 . C63 2_666 125.1(5) 0.979 2.437 3.105(11) yes C76 . H761 . C163 2_666 132.0(4) 0.979 2.490 3.227(11) yes C77 . H771 . C115 . 157.4(6) 0.930 2.360 3.238(11) yes C78 . H781 . C17 1_455 145.1(5) 0.937 2.418 3.232(11) yes C78 . H781 . C18 1_455 169.6(3) 0.937 2.460 3.386(11) yes C181 . H812 . C179 . 135.2(13) 1.003 1.495 2.317(11) yes C91 . H911 . N95 2_556 166.36(9) 0.957 2.582 3.519(11) yes C104 . H1041 . O80 2_666 176.7(3) 0.973 2.551 3.523(11) yes C76 . H1762 . C178 . 126.0(10) 1.088 2.201 2.974(11) yes O80 . H1781 . C176 . 125.5(10) 1.144 2.362 3.167(11) yes C179 . H1792 . O65 2_566 162.3(3) 0.965 1.918 2.853(11) yes C181 . H1812 . C105 1_456 128.0(3) 0.974 2.522 3.215(11) yes C181 . H1811 . C64 2_566 172.0(4) 0.982 2.362 3.337(11) yes C181 . H1811 . O65 2_566 138.9(3) 0.982 2.524 3.328(11) yes C82 . H1821 . O43 2_566 169.5(16) 1.076 2.407 3.471(11) yes C182 . H1821 . O43 2_566 152.5(3) 0.965 2.407 3.293(11) yes C63 . H1631 . C76 2_666 134.6(13) 1.046 2.280 3.105(11) yes C163 . H1631 . C76 2_666 151.4(4) 1.035 2.280 3.227(11) yes C64 . H1632 . N61 . 120.5(7) 1.095 2.502 3.200(11) yes # 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 -3 2 0 x . -1 -4 3 x .