#------------------------------------------------------------------------------ #$Date: 2024-10-03 03:47:38 +0300 (Thu, 03 Oct 2024) $ #$Revision: 295001 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160166.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7160166 loop_ _publ_author_name 'Surina, Anastasia' 'Cejka, Jan' 'Salvadori, Karolina' 'Lhotak, Pavel' _publ_section_title ; Anion Recognition Using meta-Substituted Ureidocalix[4]arene Receptors ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01441C _journal_year 2024 _chemical_formula_moiety 'C49 H61.00 N3 O9' _chemical_formula_sum 'C49 H61 N3 O9' _chemical_formula_weight 836.04 _chemical_melting_point 417.5(15) _chemical_name_common 'ureido receptor, calix[4]arene' _chemical_name_systematic '4-{N?-(4-nitrophenyl)ureido}-25,26,27,28-tetrapropoxy-calix[4]arene (cone)' _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _audit_update_record ; 2024-09-02 deposited with the CCDC. 2024-10-02 downloaded from the CCDC. ; _cell_angle_alpha 98.430(2) _cell_angle_beta 106.068(2) _cell_angle_gamma 95.002(2) _cell_formula_units_Z 2 _cell_length_a 9.3111(4) _cell_length_b 15.9194(7) _cell_length_c 16.2178(7) _cell_measurement_reflns_used 9757 _cell_measurement_temperature 180 _cell_measurement_theta_max 68.16 _cell_measurement_theta_min 2.83 _cell_volume 2264.31(17) _computing_cell_refinement 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_data_collection 'Apex4 (Bruker AXS, 2019)' _computing_data_reduction 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 180 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_unetI/netI 0.065 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 163208 _diffrn_reflns_theta_full 68.000 _diffrn_reflns_theta_max 68.550 _diffrn_reflns_theta_min 2.832 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.680 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 895.999 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.295 _exptl_crystal_size_mid 0.209 _exptl_crystal_size_min 0.202 _refine_diff_density_max 0.51 _refine_diff_density_min -0.26 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 560 _refine_ls_number_reflns 8272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0552 _refine_ls_shift/su_max 0.0003701 _refine_ls_shift/su_mean 0.0000366 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.91P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1465 _refine_ls_wR_factor_gt 0.1382 _refine_ls_wR_factor_ref 0.1462 _reflns_limit_h_max 10 _reflns_limit_h_min -11 _reflns_limit_k_max 18 _reflns_limit_k_min -19 _reflns_limit_l_max 19 _reflns_limit_l_min 0 _reflns_number_gt 7054 _reflns_number_total 8291 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 3.92 _oxford_diffrn_Wilson_scale 32.95 _oxford_refine_ls_scale 0.18764(11) _iucr_refine_instructions_details ; # # Punched on 19/07/24 at 10:37:54 # #LIST 12 BLOCK SCALE X'S U'S SUMFIX PART(1001, OCC) CONTINUE AND PART(1002, OCC) RIDE C ( 2,X'S) H ( 21,X'S) H ( 22,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE N ( 29,X'S) H ( 291,X'S) RIDE N ( 32,X'S) H ( 321,X'S) RIDE C ( 34,X'S) H ( 341,X'S) RIDE C ( 35,X'S) H ( 351,X'S) RIDE C ( 37,X'S) H ( 371,X'S) RIDE C ( 38,X'S) H ( 381,X'S) RIDE C ( 43,X'S) H ( 431,X'S) H ( 432,X'S) RIDE C ( 44,X'S) H ( 441,X'S) H ( 442,X'S) RIDE C ( 45,X'S) H ( 453,X'S) H ( 452,X'S) H ( 451,X'S) RIDE C ( 47,X'S) H ( 471,X'S) H ( 472,X'S) RIDE C ( 48,X'S) H ( 481,X'S) H ( 482,X'S) RIDE C ( 49,X'S) H ( 491,X'S) H ( 492,X'S) H ( 493,X'S) RIDE C ( 51,X'S) H ( 511,X'S) H ( 512,X'S) RIDE C ( 52,X'S) H ( 521,X'S) H ( 522,X'S) RIDE C ( 53,X'S) H ( 531,X'S) H ( 532,X'S) H ( 533,X'S) RIDE C ( 55,X'S) H ( 551,X'S) H ( 552,X'S) RIDE C ( 56,X'S) H ( 561,X'S) H ( 562,X'S) RIDE C ( 57,X'S) H ( 571,X'S) H ( 572,X'S) H ( 573,X'S) RIDE O ( 60,X'S) H ( 601,X'S) RIDE C ( 61,X'S) H ( 611,X'S) H ( 612,X'S) H ( 613,X'S) RIDE O ( 70,X'S) H ( 701,X'S) RIDE C ( 71,X'S) H ( 711,X'S) H ( 712,X'S) H ( 715,X'S) CONT H ( 714,X'S) H ( 713,X'S) H ( 716,X'S) RIDE O ( 72,X'S) H ( 721,X'S) END # # Punched on 19/07/24 at 10:37:54 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _cod_data_source_file d4ob01441c2.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '416-419' was changed to '417.5(15)' -- the average value was taken and precision was estimated. data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_sg_symbol_H-M 'P -1 ' _cod_original_formula_sum 'C49 H61.00 N3 O9' _cod_database_code 7160166 _oxford_refine_reflns_threshold_expression I>-3.0\s(I) _refine_ls_r_factor_ref 0.0632 _reflns_number_all 8282 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 0.8394(2) 0.31784(12) 0.90166(13) 0.0376 1.0000 Uani . . . . . . C2 C 0.9477(2) 0.29285(13) 0.98031(13) 0.0419 1.0000 Uani . . . . . . C3 C 0.9039(2) 0.20015(13) 0.98605(13) 0.0393 1.0000 Uani . . . . . . C4 C 0.8395(2) 0.17652(14) 1.04880(13) 0.0410 1.0000 Uani . . . . . . C5 C 0.7832(3) 0.09165(14) 1.04423(14) 0.0471 1.0000 Uani . . . . . . C6 C 0.7873(3) 0.02959(14) 0.97597(14) 0.0475 1.0000 Uani . . . . . . C7 C 0.8520(2) 0.04944(13) 0.91294(13) 0.0425 1.0000 Uani . . . . . . C8 C 0.8379(3) -0.01635(14) 0.83243(14) 0.0458 1.0000 Uani . . . . . . C9 C 0.7307(2) 0.00921(13) 0.75343(14) 0.0425 1.0000 Uani . . . . . . C10 C 0.5879(3) 0.02660(14) 0.75488(15) 0.0477 1.0000 Uani . . . . . . C11 C 0.4949(3) 0.05745(16) 0.68692(16) 0.0523 1.0000 Uani . . . . . . C12 C 0.5458(3) 0.07370(15) 0.61803(15) 0.0491 1.0000 Uani . . . . . . C13 C 0.6876(2) 0.05715(13) 0.61373(13) 0.0436 1.0000 Uani . . . . . . C14 C 0.7462(3) 0.08259(15) 0.54136(14) 0.0488 1.0000 Uani . . . . . . C15 C 0.7245(2) 0.17415(15) 0.53304(13) 0.0450 1.0000 Uani . . . . . . C16 C 0.6140(3) 0.19451(17) 0.46409(15) 0.0536 1.0000 Uani . . . . . . C17 C 0.5835(3) 0.27761(18) 0.46324(15) 0.0575 1.0000 Uani . . . . . . C18 C 0.6584(3) 0.34174(16) 0.53347(15) 0.0517 1.0000 Uani . . . . . . C19 C 0.7697(2) 0.32423(14) 0.60379(14) 0.0438 1.0000 Uani . . . . . . C20 C 0.8370(3) 0.39097(14) 0.68591(14) 0.0457 1.0000 Uani . . . . . . C21 C 0.7864(2) 0.36484(12) 0.76105(13) 0.0395 1.0000 Uani . . . . . . C22 C 0.6325(2) 0.35171(14) 0.75301(14) 0.0448 1.0000 Uani . . . . . . C23 C 0.5826(2) 0.32369(15) 0.81797(15) 0.0485 1.0000 Uani . . . . . . C24 C 0.6852(2) 0.30582(14) 0.89092(14) 0.0443 1.0000 Uani . . . . . . C25 C 0.8877(2) 0.34931(12) 0.83659(13) 0.0376 1.0000 Uani . . . . . . C26 C 0.8062(2) 0.24090(14) 0.60020(13) 0.0420 1.0000 Uani . . . . . . C27 C 0.7768(2) 0.02243(13) 0.68120(13) 0.0420 1.0000 Uani . . . . . . C28 C 0.9148(2) 0.13456(13) 0.92097(12) 0.0388 1.0000 Uani . . . . . . N29 N 0.82836(19) 0.23916(12) 1.11903(11) 0.0438 1.0000 Uani . . . . . . C30 C 0.9513(2) 0.27111(14) 1.18836(13) 0.0425 1.0000 Uani . . . . . . O31 O 1.08066(17) 0.26463(11) 1.18760(10) 0.0565 1.0000 Uani . . . . . . N32 N 0.9137(2) 0.31165(12) 1.25935(11) 0.0468 1.0000 Uani . . . . . . C33 C 1.0121(2) 0.34800(13) 1.34128(13) 0.0422 1.0000 Uani . . . . . . C34 C 0.9503(3) 0.36254(14) 1.41053(14) 0.0476 1.0000 Uani . . . . . . C35 C 1.0388(3) 0.40089(15) 1.49230(15) 0.0509 1.0000 Uani . . . . . . C36 C 1.1905(3) 0.42516(14) 1.50557(14) 0.0464 1.0000 Uani . . . . . . C37 C 1.2553(3) 0.41020(15) 1.43863(14) 0.0485 1.0000 Uani . . . . . . C38 C 1.1666(2) 0.37140(15) 1.35668(14) 0.0466 1.0000 Uani . . . . . . N39 N 1.2853(3) 0.46734(13) 1.59192(13) 0.0581 1.0000 Uani . . . . . . O40 O 1.2280(3) 0.47601(14) 1.65162(12) 0.0817 1.0000 Uani . . . . . . O41 O 1.4183(2) 0.49289(14) 1.60129(12) 0.0743 1.0000 Uani . . . . . . O42 O 1.04128(15) 0.36281(9) 0.84599(9) 0.0430 1.0000 Uani . . . . . . C43 C 1.1078(3) 0.44821(15) 0.88400(17) 0.0552 1.0000 Uani . . . . . . C44 C 1.2706(3) 0.45842(17) 0.88439(19) 0.0631 1.0000 Uani . . . . . . C45 C 1.3456(4) 0.5480(2) 0.9225(3) 0.0872 1.0000 Uani . . . . . . O46 O 0.91658(16) 0.22082(9) 0.66852(9) 0.0442 1.0000 Uani . . . . . . C47 C 1.0686(3) 0.24913(16) 0.67005(15) 0.0531 1.0000 Uani . . . . . . C48 C 1.1211(3) 0.1963(2) 0.60359(18) 0.0670 1.0000 Uani . . . . . . C49 C 1.2783(3) 0.2311(2) 0.6041(2) 0.0696 1.0000 Uani . . . . . . O50 O 0.91790(17) 0.00391(10) 0.67771(10) 0.0485 1.0000 Uani . . . . . . C51 C 0.9138(3) -0.08315(19) 0.6357(2) 0.0762 1.0000 Uani . . . . . . C52 C 1.0682(4) -0.0964(2) 0.6315(2) 0.0839 1.0000 Uani . . . . . . C53 C 1.1838(3) -0.0842(2) 0.7161(2) 0.0736 1.0000 Uani . . . . . . O54 O 0.97767(16) 0.15779(9) 0.85895(9) 0.0428 1.0000 Uani . . . . . . C55 C 1.1223(3) 0.13049(15) 0.86290(15) 0.0501 1.0000 Uani . . . . . . C56 C 1.2500(3) 0.18804(17) 0.93087(18) 0.0614 1.0000 Uani . . . . . . C57 C 1.4000(3) 0.1552(2) 0.9333(2) 0.0815 1.0000 Uani . . . . . . O60 O 0.57794(18) 0.27133(12) 1.19457(13) 0.0665 1.0000 Uani . . . . . . C61 C 0.4839(4) 0.2002(2) 1.2011(3) 0.0890 1.0000 Uani . . . . . . O70 O 0.3210(3) 0.34934(19) 1.1405(2) 0.0735 0.600(5) Uani . . P 1 1 . C71 C 0.3078(4) 0.4311(2) 1.1608(2) 0.0808 1.0000 Uani . . . . . . O72 O 0.4282(6) 0.4068(4) 1.2248(4) 0.0905 0.400(5) Uani . . P 1 2 . H21 H 1.0509 0.3007 0.9765 0.0495 1.0000 Uiso R . . . . . H22 H 0.9422 0.3286 1.0325 0.0503 1.0000 Uiso R . . . . . H51 H 0.7418 0.0780 1.0863 0.0570 1.0000 Uiso R . . . . . H61 H 0.7451 -0.0282 0.9720 0.0560 1.0000 Uiso R . . . . . H81 H 0.9368 -0.0220 0.8232 0.0543 1.0000 Uiso R . . . . . H82 H 0.7963 -0.0720 0.8414 0.0553 1.0000 Uiso R . . . . . H101 H 0.5564 0.0182 0.8032 0.0565 1.0000 Uiso R . . . . . H111 H 0.4000 0.0684 0.6892 0.0630 1.0000 Uiso R . . . . . H121 H 0.4847 0.0988 0.5750 0.0587 1.0000 Uiso R . . . . . H141 H 0.8542 0.0763 0.5545 0.0584 1.0000 Uiso R . . . . . H142 H 0.6939 0.0446 0.4869 0.0595 1.0000 Uiso R . . . . . H161 H 0.5585 0.1506 0.4178 0.0647 1.0000 Uiso R . . . . . H171 H 0.5123 0.2925 0.4176 0.0687 1.0000 Uiso R . . . . . H181 H 0.6335 0.3977 0.5339 0.0614 1.0000 Uiso R . . . . . H201 H 0.9469 0.3977 0.7034 0.0542 1.0000 Uiso R . . . . . H202 H 0.8037 0.4458 0.6746 0.0556 1.0000 Uiso R . . . . . H221 H 0.5611 0.3633 0.7030 0.0537 1.0000 Uiso R . . . . . H231 H 0.4777 0.3159 0.8116 0.0577 1.0000 Uiso R . . . . . H241 H 0.6488 0.2840 0.9332 0.0523 1.0000 Uiso R . . . . . H291 H 0.7412 0.2434 1.1267 0.0521 1.0000 Uiso R . . . . . H321 H 0.8198 0.3092 1.2548 0.0556 1.0000 Uiso R . . . . . H341 H 0.8474 0.3459 1.4008 0.0568 1.0000 Uiso R . . . . . H351 H 0.9963 0.4099 1.5371 0.0603 1.0000 Uiso R . . . . . H371 H 1.3586 0.4261 1.4486 0.0585 1.0000 Uiso R . . . . . H381 H 1.2104 0.3617 1.3116 0.0560 1.0000 Uiso R . . . . . H431 H 1.0547 0.4891 0.8515 0.0656 1.0000 Uiso R . . . . . H432 H 1.0993 0.4592 0.9430 0.0631 1.0000 Uiso R . . . . . H441 H 1.2795 0.4502 0.8242 0.0756 1.0000 Uiso R . . . . . H442 H 1.3243 0.4176 0.9197 0.0754 1.0000 Uiso R . . . . . H453 H 1.2939 0.5865 0.8841 0.1302 1.0000 Uiso R . . . . . H452 H 1.4536 0.5517 0.9259 0.1300 1.0000 Uiso R . . . . . H451 H 1.3320 0.5602 0.9822 0.1310 1.0000 Uiso R . . . . . H471 H 1.1345 0.2492 0.7285 0.0633 1.0000 Uiso R . . . . . H472 H 1.0800 0.3091 0.6604 0.0638 1.0000 Uiso R . . . . . H481 H 1.1164 0.1374 0.6154 0.0818 1.0000 Uiso R . . . . . H482 H 1.0495 0.1964 0.5468 0.0802 1.0000 Uiso R . . . . . H491 H 1.3506 0.2251 0.6578 0.1023 1.0000 Uiso R . . . . . H492 H 1.2840 0.2912 0.6013 0.1029 1.0000 Uiso R . . . . . H493 H 1.3049 0.1999 0.5553 0.1030 1.0000 Uiso R . . . . . H511 H 0.8417 -0.0923 0.5769 0.0919 1.0000 Uiso R . . . . . H512 H 0.8814 -0.1241 0.6695 0.0932 1.0000 Uiso R . . . . . H521 H 1.0618 -0.1555 0.5995 0.1015 1.0000 Uiso R . . . . . H522 H 1.0981 -0.0530 0.5980 0.1019 1.0000 Uiso R . . . . . H531 H 1.2804 -0.0969 0.7074 0.1101 1.0000 Uiso R . . . . . H532 H 1.1920 -0.0235 0.7451 0.1100 1.0000 Uiso R . . . . . H533 H 1.1515 -0.1236 0.7498 0.1101 1.0000 Uiso R . . . . . H551 H 1.1246 0.0721 0.8763 0.0593 1.0000 Uiso R . . . . . H552 H 1.1371 0.1291 0.8044 0.0600 1.0000 Uiso R . . . . . H561 H 1.2319 0.1901 0.9891 0.0732 1.0000 Uiso R . . . . . H562 H 1.2514 0.2460 0.9168 0.0730 1.0000 Uiso R . . . . . H571 H 1.4170 0.1557 0.8765 0.1214 1.0000 Uiso R . . . . . H572 H 1.4805 0.1936 0.9783 0.1221 1.0000 Uiso R . . . . . H573 H 1.3980 0.0967 0.9442 0.1217 1.0000 Uiso R . . . . . H601 H 0.5349 0.3144 1.1944 0.0998 1.0000 Uiso R . . . . . H611 H 0.3785 0.2057 1.1784 0.1337 1.0000 Uiso R . . . . . H612 H 0.5052 0.1490 1.1687 0.1335 1.0000 Uiso R . . . . . H613 H 0.5075 0.1940 1.2609 0.1337 1.0000 Uiso R . . . . . H701 H 0.2615 0.3202 1.1560 0.1108 0.600(5) Uiso R . P 1 1 . H721 H 0.4636 0.4466 1.2666 0.1378 0.400(5) Uiso R . P 1 2 . H714 H 0.2714 0.3841 1.1122 0.1221 0.400(5) Uiso R . P 1 2 . H713 H 0.2249 0.4430 1.1839 0.1216 0.400(5) Uiso R . P 1 2 . H716 H 0.3407 0.4803 1.1395 0.1219 0.400(5) Uiso R . P 1 2 . H711 H 0.4000 0.4647 1.1628 0.1221 0.600(5) Uiso R . P 1 1 . H712 H 0.2910 0.4428 1.2170 0.1222 0.600(5) Uiso R . P 1 1 . H715 H 0.2255 0.4472 1.1178 0.1222 0.600(5) Uiso R . P 1 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 0.0395(10) 0.0357(10) 0.0352(10) 0.0018(8) 0.0109(8) 0.0009(8) C2 0.0454(11) 0.0426(11) 0.0341(10) 0.0015(8) 0.0102(9) 0.0002(9) C3 0.0364(10) 0.0445(11) 0.0326(10) 0.0074(8) 0.0038(8) 0.0015(8) C4 0.0379(10) 0.0503(12) 0.0317(10) 0.0065(9) 0.0061(8) 0.0046(9) C5 0.0497(12) 0.0543(13) 0.0392(11) 0.0142(10) 0.0148(10) 0.0014(10) C6 0.0525(13) 0.0440(12) 0.0432(12) 0.0118(9) 0.0097(10) -0.0016(10) C7 0.0451(11) 0.0431(11) 0.0366(11) 0.0081(9) 0.0074(9) 0.0055(9) C8 0.0500(12) 0.0407(11) 0.0435(12) 0.0051(9) 0.0108(10) 0.0032(9) C9 0.0452(11) 0.0370(10) 0.0393(11) -0.0000(8) 0.0082(9) -0.0005(9) C10 0.0495(12) 0.0490(12) 0.0438(12) 0.0066(10) 0.0155(10) -0.0001(10) C11 0.0409(12) 0.0598(14) 0.0565(14) 0.0112(11) 0.0148(10) 0.0058(10) C12 0.0461(12) 0.0531(13) 0.0426(12) 0.0075(10) 0.0059(10) 0.0028(10) C13 0.0458(12) 0.0415(11) 0.0369(11) -0.0021(9) 0.0084(9) -0.0010(9) C14 0.0533(13) 0.0532(13) 0.0355(11) -0.0011(9) 0.0118(10) 0.0023(10) C15 0.0463(12) 0.0567(13) 0.0324(10) 0.0056(9) 0.0145(9) 0.0037(10) C16 0.0496(13) 0.0699(16) 0.0370(12) 0.0042(11) 0.0090(10) 0.0056(11) C17 0.0511(13) 0.0798(18) 0.0409(13) 0.0147(12) 0.0079(10) 0.0162(12) C18 0.0528(13) 0.0603(14) 0.0478(13) 0.0179(11) 0.0175(11) 0.0157(11) C19 0.0457(12) 0.0515(12) 0.0381(11) 0.0129(9) 0.0167(9) 0.0046(9) C20 0.0505(12) 0.0445(12) 0.0445(12) 0.0132(9) 0.0159(10) 0.0039(9) C21 0.0416(11) 0.0362(10) 0.0402(11) 0.0057(8) 0.0124(9) 0.0041(8) C22 0.0412(11) 0.0486(12) 0.0420(12) 0.0086(9) 0.0073(9) 0.0068(9) C23 0.0354(11) 0.0564(13) 0.0524(13) 0.0081(10) 0.0126(10) 0.0032(9) C24 0.0439(12) 0.0506(12) 0.0409(11) 0.0078(9) 0.0178(9) 0.0022(9) C25 0.0358(10) 0.0358(10) 0.0404(11) 0.0026(8) 0.0132(8) 0.0015(8) C26 0.0429(11) 0.0519(12) 0.0340(10) 0.0117(9) 0.0141(9) 0.0053(9) C27 0.0421(11) 0.0384(11) 0.0391(11) -0.0046(8) 0.0092(9) -0.0001(8) C28 0.0394(10) 0.0438(11) 0.0309(10) 0.0087(8) 0.0066(8) 0.0034(8) N29 0.0382(9) 0.0569(11) 0.0345(9) 0.0056(8) 0.0095(7) 0.0046(8) C30 0.0406(11) 0.0506(12) 0.0359(11) 0.0077(9) 0.0116(9) 0.0028(9) O31 0.0396(8) 0.0794(12) 0.0448(9) -0.0043(8) 0.0120(7) 0.0044(8) N32 0.0367(9) 0.0618(12) 0.0376(9) -0.0003(8) 0.0102(7) 0.0014(8) C33 0.0434(11) 0.0443(11) 0.0376(11) 0.0070(9) 0.0106(9) 0.0030(9) C34 0.0464(12) 0.0521(13) 0.0435(12) 0.0034(10) 0.0170(10) -0.0011(10) C35 0.0631(15) 0.0525(13) 0.0384(12) 0.0067(10) 0.0192(10) 0.0028(11) C36 0.0553(13) 0.0431(11) 0.0356(11) 0.0078(9) 0.0055(10) 0.0030(10) C37 0.0428(12) 0.0534(13) 0.0449(12) 0.0097(10) 0.0062(10) 0.0036(10) C38 0.0443(12) 0.0564(13) 0.0387(11) 0.0069(10) 0.0138(9) 0.0026(10) N39 0.0710(15) 0.0570(12) 0.0384(11) 0.0074(9) 0.0047(10) 0.0062(10) O40 0.1000(16) 0.0957(15) 0.0380(10) -0.0008(9) 0.0133(10) -0.0036(12) O41 0.0620(12) 0.0877(14) 0.0533(11) 0.0005(9) -0.0050(9) -0.0038(10) O42 0.0368(7) 0.0469(8) 0.0449(8) 0.0075(6) 0.0136(6) -0.0003(6) C43 0.0484(13) 0.0486(13) 0.0650(15) 0.0050(11) 0.0159(11) -0.0022(10) C44 0.0452(13) 0.0671(16) 0.0704(17) 0.0024(13) 0.0143(12) -0.0024(11) C45 0.0632(18) 0.075(2) 0.116(3) 0.0019(19) 0.0287(18) -0.0120(15) O46 0.0464(8) 0.0488(8) 0.0361(8) 0.0105(6) 0.0090(6) 0.0045(6) C47 0.0474(13) 0.0603(14) 0.0475(13) 0.0114(11) 0.0061(10) 0.0083(11) C48 0.0521(14) 0.0807(19) 0.0609(16) 0.0010(14) 0.0107(12) 0.0098(13) C49 0.0506(14) 0.0805(19) 0.0777(19) 0.0123(15) 0.0175(13) 0.0158(13) O50 0.0472(8) 0.0513(9) 0.0447(8) -0.0007(7) 0.0134(7) 0.0101(7) C51 0.0706(18) 0.0718(18) 0.0698(18) -0.0258(14) 0.0114(14) 0.0173(14) C52 0.103(2) 0.095(2) 0.0605(18) 0.0054(16) 0.0285(17) 0.0505(19) C53 0.0733(18) 0.081(2) 0.077(2) 0.0235(16) 0.0296(16) 0.0271(15) O54 0.0488(8) 0.0458(8) 0.0364(7) 0.0102(6) 0.0154(6) 0.0059(6) C55 0.0535(13) 0.0522(13) 0.0480(13) 0.0108(10) 0.0199(10) 0.0064(10) C56 0.0553(14) 0.0603(15) 0.0682(17) 0.0162(13) 0.0173(12) 0.0000(12) C57 0.0529(16) 0.090(2) 0.112(3) 0.0382(19) 0.0324(16) 0.0040(15) O60 0.0465(9) 0.0652(11) 0.0931(14) 0.0177(10) 0.0271(9) 0.0081(8) C61 0.0701(19) 0.091(2) 0.111(3) 0.041(2) 0.0263(18) 0.0018(17) O70 0.0547(18) 0.0558(19) 0.116(3) 0.0068(17) 0.0385(19) 0.0093(14) C71 0.076(2) 0.079(2) 0.093(2) 0.0135(17) 0.0346(18) 0.0123(16) O72 0.072(4) 0.088(4) 0.087(4) -0.030(3) 0.006(3) 0.008(3) 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' B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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 . C24 . 119.67(18) yes C2 . C1 . C25 . 122.54(18) yes C24 . C1 . C25 . 117.72(19) yes C1 . C2 . C3 . 110.53(16) yes C1 . C2 . H21 . 110.2 no C3 . C2 . H21 . 109.7 no C1 . C2 . H22 . 108.9 no C3 . C2 . H22 . 108.1 no H21 . C2 . H22 . 109.4 no C2 . C3 . C4 . 123.15(19) yes C2 . C3 . C28 . 119.24(18) yes C4 . C3 . C28 . 117.34(18) yes C3 . C4 . C5 . 120.78(19) yes C3 . C4 . N29 . 120.92(19) yes C5 . C4 . N29 . 118.30(18) yes C4 . C5 . C6 . 120.2(2) yes C4 . C5 . H51 . 118.9 no C6 . C5 . H51 . 120.9 no C5 . C6 . C7 . 121.3(2) yes C5 . C6 . H61 . 119.8 no C7 . C6 . H61 . 118.9 no C6 . C7 . C8 . 120.64(19) yes C6 . C7 . C28 . 117.73(19) yes C8 . C7 . C28 . 121.22(19) yes C7 . C8 . C9 . 109.35(17) yes C7 . C8 . H81 . 111.2 no C9 . C8 . H81 . 110.6 no C7 . C8 . H82 . 108.1 no C9 . C8 . H82 . 109.3 no H81 . C8 . H82 . 108.2 no C8 . C9 . C10 . 120.3(2) yes C8 . C9 . C27 . 121.25(19) yes C10 . C9 . C27 . 118.2(2) yes C9 . C10 . C11 . 120.8(2) yes C9 . C10 . H101 . 118.7 no C11 . C10 . H101 . 120.4 no C10 . C11 . C12 . 119.8(2) yes C10 . C11 . H111 . 119.3 no C12 . C11 . H111 . 120.9 no C11 . C12 . C13 . 121.4(2) yes C11 . C12 . H121 . 118.6 no C13 . C12 . H121 . 119.9 no C12 . C13 . C14 . 120.3(2) yes C12 . C13 . C27 . 117.8(2) yes C14 . C13 . C27 . 121.8(2) yes C13 . C14 . C15 . 110.20(18) yes C13 . C14 . H141 . 109.2 no C15 . C14 . H141 . 109.9 no C13 . C14 . H142 . 109.8 no C15 . C14 . H142 . 110.1 no H141 . C14 . H142 . 107.6 no C14 . C15 . C16 . 121.9(2) yes C14 . C15 . C26 . 119.78(19) yes C16 . C15 . C26 . 118.0(2) yes C15 . C16 . C17 . 121.0(2) yes C15 . C16 . H161 . 119.4 no C17 . C16 . H161 . 119.6 no C16 . C17 . C18 . 120.0(2) yes C16 . C17 . H171 . 122.2 no C18 . C17 . H171 . 117.7 no C17 . C18 . C19 . 120.9(2) yes C17 . C18 . H181 . 119.6 no C19 . C18 . H181 . 119.5 no C18 . C19 . C20 . 121.0(2) yes C18 . C19 . C26 . 118.0(2) yes C20 . C19 . C26 . 120.68(19) yes C19 . C20 . C21 . 110.45(17) yes C19 . C20 . H201 . 111.4 no C21 . C20 . H201 . 107.7 no C19 . C20 . H202 . 108.7 no C21 . C20 . H202 . 109.8 no H201 . C20 . H202 . 108.8 no C20 . C21 . C22 . 119.24(19) yes C20 . C21 . C25 . 122.45(18) yes C22 . C21 . C25 . 118.23(19) yes C21 . C22 . C23 . 120.7(2) yes C21 . C22 . H221 . 120.0 no C23 . C22 . H221 . 119.2 no C22 . C23 . C24 . 119.9(2) yes C22 . C23 . H231 . 119.4 no C24 . C23 . H231 . 120.7 no C1 . C24 . C23 . 121.4(2) yes C1 . C24 . H241 . 119.9 no C23 . C24 . H241 . 118.8 no C1 . C25 . C21 . 121.99(18) yes C1 . C25 . O42 . 119.00(18) yes C21 . C25 . O42 . 118.97(17) yes C15 . C26 . C19 . 121.8(2) yes C15 . C26 . O46 . 118.05(19) yes C19 . C26 . O46 . 119.90(19) yes C13 . C27 . C9 . 121.9(2) yes C13 . C27 . O50 . 118.92(19) yes C9 . C27 . O50 . 119.15(19) yes C3 . C28 . C7 . 122.45(19) yes C3 . C28 . O54 . 117.39(17) yes C7 . C28 . O54 . 119.88(18) yes C4 . N29 . C30 . 120.71(17) yes C4 . N29 . H291 . 118.8 no C30 . N29 . H291 . 117.1 no N29 . C30 . O31 . 123.48(19) yes N29 . C30 . N32 . 112.69(18) yes O31 . C30 . N32 . 123.84(19) yes C30 . N32 . C33 . 127.10(18) yes C30 . N32 . H321 . 116.7 no C33 . N32 . H321 . 115.8 no N32 . C33 . C34 . 117.41(19) yes N32 . C33 . C38 . 123.50(19) yes C34 . C33 . C38 . 119.1(2) yes C33 . C34 . C35 . 120.8(2) yes C33 . C34 . H341 . 119.4 no C35 . C34 . H341 . 119.9 no C34 . C35 . C36 . 119.1(2) yes C34 . C35 . H351 . 119.7 no C36 . C35 . H351 . 121.2 no C35 . C36 . C37 . 121.4(2) yes C35 . C36 . N39 . 119.6(2) yes C37 . C36 . N39 . 119.0(2) yes C36 . C37 . C38 . 119.5(2) yes C36 . C37 . H371 . 120.6 no C38 . C37 . H371 . 119.9 no C33 . C38 . C37 . 120.1(2) yes C33 . C38 . H381 . 120.6 no C37 . C38 . H381 . 119.3 no C36 . N39 . O40 . 118.2(2) yes C36 . N39 . O41 . 118.6(2) yes O40 . N39 . O41 . 123.1(2) yes C25 . O42 . C43 . 113.05(16) yes O42 . C43 . C44 . 109.1(2) yes O42 . C43 . H431 . 111.0 no C44 . C43 . H431 . 109.5 no O42 . C43 . H432 . 107.8 no C44 . C43 . H432 . 111.2 no H431 . C43 . H432 . 108.2 no C43 . C44 . C45 . 111.3(2) yes C43 . C44 . H441 . 111.4 no C45 . C44 . H441 . 103.4 no C43 . C44 . H442 . 108.5 no C45 . C44 . H442 . 109.6 no H441 . C44 . H442 . 112.5 no C44 . C45 . H453 . 107.8 no C44 . C45 . H452 . 109.5 no H453 . C45 . H452 . 111.0 no C44 . C45 . H451 . 105.6 no H453 . C45 . H451 . 111.7 no H452 . C45 . H451 . 111.1 no C26 . O46 . C47 . 114.41(16) yes O46 . C47 . C48 . 113.8(2) yes O46 . C47 . H471 . 107.8 no C48 . C47 . H471 . 110.4 no O46 . C47 . H472 . 111.5 no C48 . C47 . H472 . 107.0 no H471 . C47 . H472 . 106.0 no C47 . C48 . C49 . 112.1(2) yes C47 . C48 . H481 . 107.2 no C49 . C48 . H481 . 111.8 no C47 . C48 . H482 . 107.2 no C49 . C48 . H482 . 109.8 no H481 . C48 . H482 . 108.6 no C48 . C49 . H491 . 109.7 no C48 . C49 . H492 . 110.2 no H491 . C49 . H492 . 107.5 no C48 . C49 . H493 . 110.5 no H491 . C49 . H493 . 108.8 no H492 . C49 . H493 . 110.2 no C27 . O50 . C51 . 112.35(18) yes O50 . C51 . C52 . 108.8(2) yes O50 . C51 . H511 . 108.5 no C52 . C51 . H511 . 111.1 no O50 . C51 . H512 . 110.4 no C52 . C51 . H512 . 108.7 no H511 . C51 . H512 . 109.4 no C51 . C52 . C53 . 115.2(3) yes C51 . C52 . H521 . 107.5 no C53 . C52 . H521 . 109.6 no C51 . C52 . H522 . 106.3 no C53 . C52 . H522 . 107.7 no H521 . C52 . H522 . 110.4 no C52 . C53 . H531 . 109.7 no C52 . C53 . H532 . 107.8 no H531 . C53 . H532 . 110.9 no C52 . C53 . H533 . 107.6 no H531 . C53 . H533 . 109.7 no H532 . C53 . H533 . 111.1 no C28 . O54 . C55 . 115.12(16) yes O54 . C55 . C56 . 112.89(19) yes O54 . C55 . H551 . 110.6 no C56 . C55 . H551 . 107.6 no O54 . C55 . H552 . 107.7 no C56 . C55 . H552 . 110.0 no H551 . C55 . H552 . 108.0 no C55 . C56 . C57 . 110.7(2) yes C55 . C56 . H561 . 109.0 no C57 . C56 . H561 . 109.9 no C55 . C56 . H562 . 108.4 no C57 . C56 . H562 . 110.2 no H561 . C56 . H562 . 108.7 no C56 . C57 . H571 . 108.4 no C56 . C57 . H572 . 108.7 no H571 . C57 . H572 . 109.4 no C56 . C57 . H573 . 110.9 no H571 . C57 . H573 . 108.3 no H572 . C57 . H573 . 111.1 no C61 . O60 . H601 . 110.8 no O60 . C61 . H611 . 112.1 no O60 . C61 . H612 . 109.0 no H611 . C61 . H612 . 109.0 no O60 . C61 . H613 . 108.6 no H611 . C61 . H613 . 110.5 no H612 . C61 . H613 . 107.6 no C71 . O70 . H701 . 109.8 no O70 . C71 . H711 . 108.4 no O70 . C71 . H712 . 110.6 no H711 . C71 . H712 . 108.9 no O70 . C71 . H715 . 111.0 no H711 . C71 . H715 . 108.8 no H712 . C71 . H715 . 109.1 no O72 . C71 . H714 . 108.5 no O72 . C71 . H713 . 111.1 no H714 . C71 . H713 . 108.2 no O72 . C71 . H716 . 111.5 no H714 . C71 . H716 . 108.0 no H713 . C71 . H716 . 109.4 no C71 . O72 . H721 . 110.6 no 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 . 1.519(3) yes C1 . C24 . 1.390(3) yes C1 . C25 . 1.395(3) yes C2 . C3 . 1.519(3) yes C2 . H21 . 0.978 no C2 . H22 . 0.965 no C3 . C4 . 1.395(3) yes C3 . C28 . 1.403(3) yes C4 . C5 . 1.390(3) yes C4 . N29 . 1.433(3) yes C5 . C6 . 1.383(3) yes C5 . H51 . 0.915 no C6 . C7 . 1.382(3) yes C6 . H61 . 0.954 no C7 . C8 . 1.516(3) yes C7 . C28 . 1.401(3) yes C8 . C9 . 1.523(3) yes C8 . H81 . 0.982 no C8 . H82 . 0.983 no C9 . C10 . 1.388(3) yes C9 . C27 . 1.391(3) yes C10 . C11 . 1.382(3) yes C10 . H101 . 0.931 no C11 . C12 . 1.377(3) yes C11 . H111 . 0.925 no C12 . C13 . 1.386(3) yes C12 . H121 . 0.934 no C13 . C14 . 1.515(3) yes C13 . C27 . 1.395(3) yes C14 . C15 . 1.509(3) yes C14 . H141 . 0.986 no C14 . H142 . 0.968 no C15 . C16 . 1.394(3) yes C15 . C26 . 1.398(3) yes C16 . C17 . 1.378(4) yes C16 . H161 . 0.943 no C17 . C18 . 1.386(3) yes C17 . H171 . 0.923 no C18 . C19 . 1.393(3) yes C18 . H181 . 0.940 no C19 . C20 . 1.517(3) yes C19 . C26 . 1.395(3) yes C20 . C21 . 1.520(3) yes C20 . H201 . 0.975 no C20 . H202 . 0.977 no C21 . C22 . 1.397(3) yes C21 . C25 . 1.393(3) yes C22 . C23 . 1.378(3) yes C22 . H221 . 0.950 no C23 . C24 . 1.383(3) yes C23 . H231 . 0.949 no C24 . H241 . 0.941 no C25 . O42 . 1.389(2) yes C26 . O46 . 1.384(2) yes C27 . O50 . 1.386(3) yes C28 . O54 . 1.374(2) yes N29 . C30 . 1.361(3) yes N29 . H291 . 0.861 no C30 . O31 . 1.221(3) yes C30 . N32 . 1.382(3) yes N32 . C33 . 1.395(3) yes N32 . H321 . 0.854 no C33 . C34 . 1.397(3) yes C33 . C38 . 1.397(3) yes C34 . C35 . 1.371(3) yes C34 . H341 . 0.934 no C35 . C36 . 1.380(3) yes C35 . H351 . 0.919 no C36 . C37 . 1.382(3) yes C36 . N39 . 1.459(3) yes C37 . C38 . 1.376(3) yes C37 . H371 . 0.936 no C38 . H381 . 0.931 no N39 . O40 . 1.225(3) yes N39 . O41 . 1.230(3) yes O42 . C43 . 1.417(3) yes C43 . C44 . 1.509(3) yes C43 . H431 . 0.979 no C43 . H432 . 0.973 no C44 . C45 . 1.494(4) yes C44 . H441 . 0.994 no C44 . H442 . 1.004 no C45 . H453 . 0.997 no C45 . H452 . 0.988 no C45 . H451 . 1.005 no O46 . C47 . 1.440(3) yes C47 . C48 . 1.485(4) yes C47 . H471 . 0.975 no C47 . H472 . 0.991 no C48 . C49 . 1.517(4) yes C48 . H481 . 0.983 no C48 . H482 . 0.976 no C49 . H491 . 0.966 no C49 . H492 . 0.962 no C49 . H493 . 0.974 no O50 . C51 . 1.444(3) yes C51 . C52 . 1.489(4) yes C51 . H511 . 0.984 no C51 . H512 . 0.989 no C52 . C53 . 1.465(4) yes C52 . H521 . 0.994 no C52 . H522 . 1.005 no C53 . H531 . 0.981 no C53 . H532 . 0.996 no C53 . H533 . 0.971 no O54 . C55 . 1.438(3) yes C55 . C56 . 1.502(3) yes C55 . H551 . 0.985 no C55 . H552 . 0.993 no C56 . C57 . 1.526(4) yes C56 . H561 . 1.000 no C56 . H562 . 0.983 no C57 . H571 . 0.978 no C57 . H572 . 0.977 no C57 . H573 . 0.974 no O60 . C61 . 1.404(3) yes O60 . H601 . 0.823 no C61 . H611 . 0.965 no C61 . H612 . 0.970 no C61 . H613 . 0.957 no O70 . C71 . 1.320(4) yes O70 . H701 . 0.808 no C71 . H711 . 0.962 no C71 . H712 . 0.961 no C71 . H715 . 0.965 no C71 . O72 . 1.425(6) yes C71 . H714 . 0.965 no C71 . H713 . 0.968 no C71 . H716 . 0.961 no O72 . H721 . 0.826 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 N29 . H291 . O60 . 158 0.86 2.15 2.967(4) yes N32 . H321 . O60 . 157 0.85 2.18 2.988(4) yes O60 . H601 . O70 . 139 0.82 2.10 2.777(4) yes O60 . H601 . O72 . 164 0.82 1.93 2.725(4) yes O70 . H701 . O31 1_455 168 0.81 2.06 2.852(4) yes O72 . H721 . O41 2_768 157 0.83 2.15 2.933(4) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C24 . C1 . C2 . C3 . 54.1(5) yes C24 . C1 . C2 . H21 . 175.5 no C24 . C1 . C2 . H22 . -64.5 no C25 . C1 . C2 . C3 . -123.0(4) yes C25 . C1 . C2 . H21 . -1.6 no C25 . C1 . C2 . H22 . 118.5 no C2 . C1 . C24 . C23 . -176.7(4) yes C2 . C1 . C24 . H241 . 2.0 no C25 . C1 . C24 . C23 . 0.5(6) yes C25 . C1 . C24 . H241 . 179.2 no C2 . C1 . C25 . C21 . 174.2(3) yes C2 . C1 . C25 . O42 . -3.5(5) yes C24 . C1 . C25 . C21 . -2.9(5) yes C24 . C1 . C25 . O42 . 179.3(3) yes C1 . C2 . C3 . C4 . -107.7(4) yes C1 . C2 . C3 . C28 . 66.1(5) yes H21 . C2 . C3 . C4 . 130.5 no H21 . C2 . C3 . C28 . -55.7 no H22 . C2 . C3 . C4 . 11.3 no H22 . C2 . C3 . C28 . -174.9 no C2 . C3 . C4 . C5 . 171.4(4) yes C2 . C3 . C4 . N29 . -8.0(6) yes C28 . C3 . C4 . C5 . -2.6(5) yes C28 . C3 . C4 . N29 . 178.1(3) yes C2 . C3 . C28 . C7 . -168.3(4) yes C2 . C3 . C28 . O54 . 5.6(5) yes C4 . C3 . C28 . C7 . 5.9(5) yes C4 . C3 . C28 . O54 . 179.8(3) yes C3 . C4 . C5 . C6 . -1.5(6) yes C3 . C4 . C5 . H51 . 179.9 no N29 . C4 . C5 . C6 . 177.9(4) yes N29 . C4 . C5 . H51 . -0.8 no C3 . C4 . N29 . C30 . -76.9(4) yes C3 . C4 . N29 . H291 . 124.6 no C5 . C4 . N29 . C30 . 103.7(4) yes C5 . C4 . N29 . H291 . -54.8 no C4 . C5 . C6 . C7 . 2.5(6) yes C4 . C5 . C6 . H61 . -177.7 no H51 . C5 . C6 . C7 . -178.9 no H51 . C5 . C6 . H61 . 1.0 no C5 . C6 . C7 . C8 . -172.1(4) yes C5 . C6 . C7 . C28 . 0.6(6) yes H61 . C6 . C7 . C8 . 8.1 no H61 . C6 . C7 . C28 . -179.2 no C6 . C7 . C8 . C9 . 108.4(4) yes C6 . C7 . C8 . H81 . -129.2 no C6 . C7 . C8 . H82 . -10.5 no C28 . C7 . C8 . C9 . -64.0(5) yes C28 . C7 . C8 . H81 . 58.4 no C28 . C7 . C8 . H82 . 177.1 no C6 . C7 . C28 . C3 . -4.9(6) yes C6 . C7 . C28 . O54 . -178.7(3) yes C8 . C7 . C28 . C3 . 167.7(4) yes C8 . C7 . C28 . O54 . -6.1(5) yes C7 . C8 . C9 . C10 . -52.6(5) yes C7 . C8 . C9 . C27 . 122.1(4) yes H81 . C8 . C9 . C10 . -175.4 no H81 . C8 . C9 . C27 . -0.7 no H82 . C8 . C9 . C10 . 65.5 no H82 . C8 . C9 . C27 . -119.7 no C8 . C9 . C10 . C11 . 174.0(4) yes C8 . C9 . C10 . H101 . -4.7 no C27 . C9 . C10 . C11 . -1.0(6) yes C27 . C9 . C10 . H101 . -179.6 no C8 . C9 . C27 . C13 . -171.0(4) yes C8 . C9 . C27 . O50 . 6.3(6) yes C10 . C9 . C27 . C13 . 3.9(6) yes C10 . C9 . C27 . O50 . -178.8(3) yes C9 . C10 . C11 . C12 . -2.0(6) yes C9 . C10 . C11 . H111 . 179.7 no H101 . C10 . C11 . C12 . 176.6 no H101 . C10 . C11 . H111 . -1.6 no C10 . C11 . C12 . C13 . 2.1(7) yes C10 . C11 . C12 . H121 . -174.9 no H111 . C11 . C12 . C13 . -179.7 no H111 . C11 . C12 . H121 . 3.3 no C11 . C12 . C13 . C14 . -174.8(4) yes C11 . C12 . C13 . C27 . 0.7(6) yes H121 . C12 . C13 . C14 . 2.2 no H121 . C12 . C13 . C27 . 177.7 no C12 . C13 . C14 . C15 . 48.5(6) yes C12 . C13 . C14 . H141 . 169.3 no C12 . C13 . C14 . H142 . -72.9 no C27 . C13 . C14 . C15 . -126.8(5) yes C27 . C13 . C14 . H141 . -6.0 no C27 . C13 . C14 . H142 . 111.8 no C12 . C13 . C27 . C9 . -3.8(6) yes C12 . C13 . C27 . O50 . 178.9(4) yes C14 . C13 . C27 . C9 . 171.6(4) yes C14 . C13 . C27 . O50 . -5.7(6) yes C13 . C14 . C15 . C16 . -106.4(5) yes C13 . C14 . C15 . C26 . 67.0(5) yes H141 . C14 . C15 . C16 . 133.2 no H141 . C14 . C15 . C26 . -53.4 no H142 . C14 . C15 . C16 . 14.9 no H142 . C14 . C15 . C26 . -171.7 no C14 . C15 . C16 . C17 . 171.9(3) yes C14 . C15 . C16 . H161 . -7.3 no C26 . C15 . C16 . C17 . -1.6(5) yes C26 . C15 . C16 . H161 . 179.2 no C14 . C15 . C26 . C19 . -167.2(3) yes C14 . C15 . C26 . O46 . 6.6(4) yes C16 . C15 . C26 . C19 . 6.5(5) yes C16 . C15 . C26 . O46 . -179.7(3) yes C15 . C16 . C17 . C18 . -2.9(5) yes C15 . C16 . C17 . H171 . 178.6 no H161 . C16 . C17 . C18 . 176.2 no H161 . C16 . C17 . H171 . -2.2 no C16 . C17 . C18 . C19 . 2.9(5) yes C16 . C17 . C18 . H181 . -176.8 no H171 . C17 . C18 . C19 . -178.6 no H171 . C17 . C18 . H181 . 1.8 no C17 . C18 . C19 . C20 . -171.7(3) yes C17 . C18 . C19 . C26 . 1.8(5) yes H181 . C18 . C19 . C20 . 7.9 no H181 . C18 . C19 . C26 . -178.6 no C18 . C19 . C20 . C21 . 110.0(4) yes C18 . C19 . C20 . H201 . -130.4 no C18 . C19 . C20 . H202 . -10.5 no C26 . C19 . C20 . C21 . -63.3(5) yes C26 . C19 . C20 . H201 . 56.3 no C26 . C19 . C20 . H202 . 176.2 no C18 . C19 . C26 . C15 . -6.5(5) yes C18 . C19 . C26 . O46 . 179.7(3) yes C20 . C19 . C26 . C15 . 167.0(3) yes C20 . C19 . C26 . O46 . -6.8(5) yes C19 . C20 . C21 . C22 . -58.7(5) yes C19 . C20 . C21 . C25 . 118.1(5) yes H201 . C20 . C21 . C22 . 179.4 no H201 . C20 . C21 . C25 . -3.8 no H202 . C20 . C21 . C22 . 61.1 no H202 . C20 . C21 . C25 . -122.1 no C20 . C21 . C22 . C23 . 176.6(4) yes C20 . C21 . C22 . H221 . -4.8 no C25 . C21 . C22 . C23 . -0.3(6) yes C25 . C21 . C22 . H221 . 178.2 no C20 . C21 . C25 . C1 . -174.0(3) yes C20 . C21 . C25 . O42 . 3.7(5) yes C22 . C21 . C25 . C1 . 2.8(5) yes C22 . C21 . C25 . O42 . -179.4(3) yes C21 . C22 . C23 . C24 . -1.9(6) yes C21 . C22 . C23 . H231 . 179.1 no H221 . C22 . C23 . C24 . 179.5 no H221 . C22 . C23 . H231 . 0.5 no C22 . C23 . C24 . C1 . 1.9(6) yes C22 . C23 . C24 . H241 . -176.8 no H231 . C23 . C24 . C1 . -179.2 no H231 . C23 . C24 . H241 . 2.1 no C1 . C25 . O42 . C43 . -94.4(4) yes C21 . C25 . O42 . C43 . 87.7(4) yes C15 . C26 . O46 . C47 . 108.8(4) yes C19 . C26 . O46 . C47 . -77.2(4) yes C13 . C27 . O50 . C51 . -91.8(5) yes C9 . C27 . O50 . C51 . 90.8(5) yes C3 . C28 . O54 . C55 . 111.3(4) yes C7 . C28 . O54 . C55 . -74.6(5) yes C4 . N29 . C30 . O31 . 16.7(5) yes C4 . N29 . C30 . N32 . -163.4(3) yes H291 . N29 . C30 . O31 . 175.6 no H291 . N29 . C30 . N32 . -4.5 no N29 . C30 . N32 . C33 . 177.2(3) yes N29 . C30 . N32 . H321 . 5.0 no O31 . C30 . N32 . C33 . -2.9(5) yes O31 . C30 . N32 . H321 . -175.1 no C30 . N32 . C33 . C34 . -161.3(3) yes C30 . N32 . C33 . C38 . 19.7(5) yes H321 . N32 . C33 . C34 . 11.0 no H321 . N32 . C33 . C38 . -168.0 no N32 . C33 . C34 . C35 . -177.6(3) yes N32 . C33 . C34 . H341 . 2.3 no C38 . C33 . C34 . C35 . 1.4(5) yes C38 . C33 . C34 . H341 . -178.7 no N32 . C33 . C38 . C37 . 177.3(3) yes N32 . C33 . C38 . H381 . -1.8 no C34 . C33 . C38 . C37 . -1.7(5) yes C34 . C33 . C38 . H381 . 179.2 no C33 . C34 . C35 . C36 . 0.0(6) yes C33 . C34 . C35 . H351 . -179.9 no H341 . C34 . C35 . C36 . -179.9 no H341 . C34 . C35 . H351 . 0.1 no C34 . C35 . C36 . C37 . -1.2(5) yes C34 . C35 . C36 . N39 . 179.0(3) yes H351 . C35 . C36 . C37 . 178.8 no H351 . C35 . C36 . N39 . -1.1 no C35 . C36 . C37 . C38 . 0.9(5) yes C35 . C36 . C37 . H371 . -178.9 no N39 . C36 . C37 . C38 . -179.2(3) yes N39 . C36 . C37 . H371 . 0.9 no C35 . C36 . N39 . O40 . 3.7(5) yes C35 . C36 . N39 . O41 . -175.9(4) yes C37 . C36 . N39 . O40 . -176.2(4) yes C37 . C36 . N39 . O41 . 4.3(5) yes C36 . C37 . C38 . C33 . 0.5(5) yes C36 . C37 . C38 . H381 . 179.6 no H371 . C37 . C38 . C33 . -179.6 no H371 . C37 . C38 . H381 . -0.5 no C25 . O42 . C43 . C44 . -175.2(4) yes C25 . O42 . C43 . H431 . -54.4 no C25 . O42 . C43 . H432 . 63.9 no O42 . C43 . C44 . C45 . 179.0(5) yes O42 . C43 . C44 . H441 . 64.1 no O42 . C43 . C44 . H442 . -60.3 no H431 . C43 . C44 . C45 . 57.3 no H431 . C43 . C44 . H441 . -57.6 no H431 . C43 . C44 . H442 . 178.0 no H432 . C43 . C44 . C45 . -62.2 no H432 . C43 . C44 . H441 . -177.1 no H432 . C43 . C44 . H442 . 58.5 no C43 . C44 . C45 . H453 . -63.3 no C43 . C44 . C45 . H452 . 175.9 no C43 . C44 . C45 . H451 . 56.2 no H441 . C44 . C45 . H453 . 56.4 no H441 . C44 . C45 . H452 . -64.4 no H441 . C44 . C45 . H451 . 175.9 no H442 . C44 . C45 . H453 . 176.6 no H442 . C44 . C45 . H452 . 55.8 no H442 . C44 . C45 . H451 . -63.9 no C26 . O46 . C47 . C48 . -75.3(5) yes C26 . O46 . C47 . H471 . 161.8 no C26 . O46 . C47 . H472 . 45.9 no O46 . C47 . C48 . C49 . 176.8(4) yes O46 . C47 . C48 . H481 . -60.1 no O46 . C47 . C48 . H482 . 56.3 no H471 . C47 . C48 . C49 . -61.7 no H471 . C47 . C48 . H481 . 61.3 no H471 . C47 . C48 . H482 . 177.7 no H472 . C47 . C48 . C49 . 53.2 no H472 . C47 . C48 . H481 . 176.2 no H472 . C47 . C48 . H482 . -67.4 no C47 . C48 . C49 . H491 . 67.3 no C47 . C48 . C49 . H492 . -50.8 no C47 . C48 . C49 . H493 . -172.8 no H481 . C48 . C49 . H491 . -53.1 no H481 . C48 . C49 . H492 . -171.2 no H481 . C48 . C49 . H493 . 66.8 no H482 . C48 . C49 . H491 . -173.6 no H482 . C48 . C49 . H492 . 68.2 no H482 . C48 . C49 . H493 . -53.8 no C27 . O50 . C51 . C52 . 177.7(5) yes C27 . O50 . C51 . H511 . 56.7 no C27 . O50 . C51 . H512 . -63.2 no O50 . C51 . C52 . C53 . 60.6(8) yes O50 . C51 . C52 . H521 . -176.9 no O50 . C51 . C52 . H522 . -58.6 no H511 . C51 . C52 . C53 . -180.0 no H511 . C51 . C52 . H521 . -57.5 no H511 . C51 . C52 . H522 . 60.8 no H512 . C51 . C52 . C53 . -59.6 no H512 . C51 . C52 . H521 . 62.9 no H512 . C51 . C52 . H522 . -178.8 no C51 . C52 . C53 . H531 . 177.2 no C51 . C52 . C53 . H532 . -62.0 no C51 . C52 . C53 . H533 . 57.9 no H521 . C52 . C53 . H531 . 55.8 no H521 . C52 . C53 . H532 . 176.7 no H521 . C52 . C53 . H533 . -63.5 no H522 . C52 . C53 . H531 . -64.4 no H522 . C52 . C53 . H532 . 56.5 no H522 . C52 . C53 . H533 . 176.3 no C28 . O54 . C55 . C56 . -80.9(4) yes C28 . O54 . C55 . H551 . 39.7 no C28 . O54 . C55 . H552 . 157.5 no O54 . C55 . C56 . C57 . 179.0(4) yes O54 . C55 . C56 . H561 . 58.1 no O54 . C55 . C56 . H562 . -60.0 no H551 . C55 . C56 . C57 . 56.7 no H551 . C55 . C56 . H561 . -64.2 no H551 . C55 . C56 . H562 . 177.7 no H552 . C55 . C56 . C57 . -60.8 no H552 . C55 . C56 . H561 . 178.3 no H552 . C55 . C56 . H562 . 60.2 no C55 . C56 . C57 . H571 . 61.6 no C55 . C56 . C57 . H572 . -179.6 no C55 . C56 . C57 . H573 . -57.2 no H561 . C56 . C57 . H571 . -178.0 no H561 . C56 . C57 . H572 . -59.1 no H561 . C56 . C57 . H573 . 63.3 no H562 . C56 . C57 . H571 . -58.2 no H562 . C56 . C57 . H572 . 60.6 no H562 . C56 . C57 . H573 . -177.0 no H601 . O60 . C61 . H611 . 26.2 no H601 . O60 . C61 . H612 . 146.9 no H601 . O60 . C61 . H613 . -96.2 no H701 . O70 . C71 . O72 . 97.3 no H701 . O70 . C71 . H714 . -94.6 no H701 . O70 . C71 . H713 . -6.7 no H701 . O70 . C71 . H716 . -161.9 no H701 . O70 . C71 . H711 . 158.5 no H701 . O70 . C71 . H712 . 39.2 no H701 . O70 . C71 . H715 . -82.1 no O70 . C71 . O72 . H721 . -173.8 no H714 . C71 . O72 . H721 . 178.0 no H713 . C71 . O72 . H721 . -63.2 no H716 . C71 . O72 . H721 . 59.2 no H711 . C71 . O72 . H721 . 67.3 no H712 . C71 . O72 . H721 . -51.3 no loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details -1 3 2 x . -1 3 1 x . -1 0 1 x . -1 2 3 x . -4 -13 6 x . -6 4 12 x . -1 -3 9 x . 4 -1 8 x . -6 0 16 x .