#------------------------------------------------------------------------------ #$Date: 2026-05-30 02:27:28 +0100 (Sat, 30 May 2026) $ #$Revision: 306139 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577321.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_1577321 loop_ _publ_author_name 'Njoku, Sara' 'Perez Mellor, Ariel F.' 'Brazard, Johanna' 'Giuffrida, Simone G.' 'Dudziak, Wojciech' 'Besnard, C\'eline' 'B\"urgi, Thomas' 'Adachi, Takuji B. M.' 'Szweda, R\'o\.za' _publ_section_title ; Stereocontrol as a tool for shaping abiotic, sequence-defined oligourethanes ; _journal_name_full 'Polymer Chemistry' _journal_paper_doi 10.1039/D6PY00299D _journal_year 2026 _chemical_formula_moiety 'C20 H38 N4 O9' _chemical_formula_sum 'C20 H38 N4 O9' _chemical_formula_weight 478.54 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-03-05 _audit_creation_method ; Olex2 1.5 (compiled 2025.02.27 svn.r83f5de26 for OlexSys, GUI svn.r7172) ; _audit_update_record ; 2025-05-28 deposited with the CCDC. 2026-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.759 _cell_length_b 10.709 _cell_length_c 38.068 _cell_measurement_reflns_used 5000 _cell_measurement_temperature 100.15 _cell_measurement_theta_max 0.830 _cell_measurement_theta_min 0.079 _cell_volume 2347.773 _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/2 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100.15 _diffrn_measured_fraction_theta_full 0.749 _diffrn_measured_fraction_theta_max 0.749 _diffrn_measurement_device_type 'tecnai G2 sphera equipped with an ASI cheetah detector' _diffrn_radiation_type electron _diffrn_radiation_wavelength 0.0285 _diffrn_reflns_av_R_equivalents 0.1786 _diffrn_reflns_av_unetI/netI 0.4050 _diffrn_reflns_Laue_measured_fraction_full 0.749 _diffrn_reflns_Laue_measured_fraction_max 0.749 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 8442 _diffrn_reflns_point_group_measured_fraction_full 0.776 _diffrn_reflns_point_group_measured_fraction_max 0.776 _diffrn_reflns_theta_full 0.830 _diffrn_reflns_theta_max 0.830 _diffrn_reflns_theta_min 0.079 _exptl_absorpt_coefficient_mu 0.000 _exptl_crystal_density_diffrn 1.354 _exptl_crystal_description needle _exptl_crystal_F_000 388 _refine_diff_density_max 0.117 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; All f" are zero, so absolute structure could not be determined ; _refine_ls_extinction_coef 73(21) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 2001 _refine_ls_number_restraints 224 _refine_ls_restrained_S_all 0.977 _refine_ls_R_factor_all 0.1917 _refine_ls_R_factor_gt 0.1245 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1161P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2771 _refine_ls_wR_factor_ref 0.2955 _reflns_Friedel_coverage 0.721 _reflns_Friedel_fraction_full 0.817 _reflns_Friedel_fraction_max 0.817 _reflns_number_gt 911 _reflns_number_total 2001 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6py00299d2.cif _cod_data_source_block oligoC _cod_original_cell_volume 2347.6 _cod_database_code 1577321 _shelx_shelxl_version_number 2019/2 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Restrained distances O1-C2 1.42 with sigma of 0.02 C4-C3 1.54 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C11) = Uanis(C18) = Uanis(C26) = Uanis(C4) Uanis(N5) = Uanis(N12) = Uanis(N19) = Uanis(N27) Uanis(C25) = Uanis(C10) = Uanis(C3) = Uanis(C17) Uanis(O8) = Uanis(O15) = Uanis(O22) = Uanis(O30) Uanis(C20) = Uanis(C13) = Uanis(C6) = Uanis(C28) 4. Rigid body (RIGU) restrains O1, O7, O8, O14, O15, O21, O22, O29, O30, N5, N12, N19, N27, C2, C3, C4, C6, C9, C10, C11, C13, C16, C17, C18, C20, C24, C25, C26, C28, C31, C32, C33, C34 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5.a Ternary CH refined with riding coordinates: C3(H3), C10(H10), C17(H17), C25(H25) 5.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C9(H9A,H9B), C16(H16A,H16B), C24(H24A,H24B) 5.c Me refined with riding coordinates: C4(H4A,H4B,H4C) 5.d Aromatic/amide H refined with riding coordinates: N5(H5), N12(H12), N19(H19), N27(H27) 5.e Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C26(H26A,H26B,H26C), C32(H32A,H32B, H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C) 5.f Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL merge_a.res in P2(1)2(1)2(1) merge.res created by SHELXL-2019/2 at 15:53:24 on 05-Mar-2025 REM Old TITL 16 in P222 REM SHELXT solution in P2(1)2(1)2(1): R1 0.245, Rweak 0.127, Alpha 0.106 REM 0.888 for 8 systematic absences, Orientation as input REM Flack x = -7.918 ( 6.527 ) from 265 Parsons' quotients REM Formula found by SHELXT: C25 O8 CELL 0.0285 5.7588 10.7086 38.068 90 90 90 ZERR 4 0 0 0 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C 0.136 0.373 0.548 3.281 1.227 13.046 0.597 41.02 0 0 0 0 0.75 12.011 SFAC H 0.037 0.561 0.127 3.791 0.236 13.556 0.129 37.723 0 0 0 0 0.32 1.008 SFAC N 0.137 0.329 0.534 2.673 1.086 10.316 0.455 32.763 0 0 0 0 0.71 14.007 SFAC O 0.143 0.305 0.51 2.268 0.937 8.262 0.392 25.665 0 0 0 0 0.63 15.999 UNIT 80 152 16 36 RIGU O1 > C34 EADP C11 C18 C26 C4 EADP N5 N12 N19 N27 EADP C25 C10 C3 C17 EADP O8 O15 O22 O30 EADP C20 C13 C6 C28 DFIX 1.42 O1 C2 DFIX 1.54 C4 C3 L.S. 4 0 0 PLAN 2 TEMP -173 CONF list 4 fmap 2 53 MORE -1 BOND $H ACTA OMIT 2 0 8 REM REM REM WGHT 0.116100 EXTI 73.420448 FVAR 1.11641 O1 4 -0.826179 0.544677 0.076797 11.00000 0.03982 0.11566 = 0.08524 0.02137 -0.00125 -0.00382 AFIX 147 H1 2 -0.771283 0.566080 0.096334 11.00000 -1.50000 AFIX 0 O7 4 -0.553584 0.514526 0.129757 11.00000 0.03188 0.06005 = 0.03460 0.02907 0.00185 0.01565 O8 4 -0.194499 0.457416 0.128899 11.00000 0.02424 0.03501 = 0.02857 -0.00159 -0.00733 0.00427 O14 4 -0.044012 0.446595 0.233429 11.00000 0.02451 0.03606 = 0.02356 -0.00534 -0.00100 0.00344 O15 4 0.277330 0.551544 0.220482 11.00000 0.02424 0.03501 = 0.02857 -0.00159 -0.00733 0.00427 O21 4 0.395032 0.561934 0.328397 11.00000 0.02974 0.05923 = 0.02396 0.00565 0.00175 0.01241 O22 4 0.729288 0.460385 0.321339 11.00000 0.02424 0.03501 = 0.02857 -0.00159 -0.00733 0.00427 O29 4 0.985013 0.440931 0.433403 11.00000 0.04470 0.06266 = 0.03361 -0.00269 0.00608 -0.01441 O30 4 1.251726 0.570336 0.411549 11.00000 0.02424 0.03501 = 0.02857 -0.00159 -0.00733 0.00427 N5 3 -0.308501 0.568674 0.085939 11.00000 0.01547 0.03326 = 0.02439 -0.00168 -0.00596 0.00359 AFIX 43 H5 2 -0.167829 0.557293 0.077497 11.00000 -1.20000 AFIX 0 N12 3 0.141772 0.419816 0.185817 11.00000 0.01547 0.03326 = 0.02439 -0.00168 -0.00596 0.00359 AFIX 43 H12 2 0.270853 0.437904 0.174540 11.00000 -1.20000 AFIX 0 N19 3 0.613614 0.578838 0.280562 11.00000 0.01547 0.03326 = 0.02439 -0.00168 -0.00596 0.00359 AFIX 43 H19 2 0.739022 0.551715 0.269780 11.00000 -1.20000 AFIX 0 N27 3 1.080238 0.432731 0.375292 11.00000 0.01547 0.03326 = 0.02439 -0.00168 -0.00596 0.00359 AFIX 43 H27 2 1.183503 0.454809 0.359425 11.00000 -1.20000 AFIX 0 C2 1 -0.665011 0.577770 0.049289 11.00000 0.03519 0.06315 = 0.05481 0.00511 -0.02078 -0.01083 AFIX 23 H2A 2 -0.740641 0.633546 0.031991 11.00000 -1.20000 H2B 2 -0.610356 0.501925 0.036929 11.00000 -1.20000 AFIX 0 C3 1 -0.460215 0.644796 0.067005 11.00000 0.01227 0.03526 = 0.02385 0.00092 -0.00297 0.00477 AFIX 13 H3 2 -0.514451 0.717099 0.081463 11.00000 -1.20000 AFIX 0 C4 1 -0.316656 0.689948 0.034110 11.00000 0.02897 0.03914 = 0.02868 0.00126 -0.00175 0.00484 AFIX 33 H4A 2 -0.413729 0.744358 0.019521 11.00000 -1.50000 H4B 2 -0.179515 0.736239 0.042031 11.00000 -1.50000 H4C 2 -0.267485 0.617314 0.020328 11.00000 -1.50000 AFIX 0 C6 1 -0.360831 0.514654 0.114662 11.00000 0.01831 0.03409 = 0.02234 -0.00278 -0.00471 0.00492 C9 1 -0.231640 0.378929 0.158993 11.00000 0.02010 0.02974 = 0.02849 -0.00074 -0.01288 0.00334 AFIX 23 H9A 2 -0.341709 0.311321 0.152879 11.00000 -1.20000 H9B 2 -0.300569 0.428708 0.178267 11.00000 -1.20000 AFIX 0 C10 1 -0.013344 0.325112 0.170588 11.00000 0.01227 0.03526 = 0.02385 0.00092 -0.00297 0.00477 AFIX 13 H10 2 -0.053293 0.266852 0.190208 11.00000 -1.20000 AFIX 0 C11 1 0.086935 0.252004 0.144648 11.00000 0.02897 0.03914 = 0.02868 0.00126 -0.00175 0.00484 AFIX 137 H11A 2 0.095300 0.299678 0.122710 11.00000 -1.50000 H11B 2 -0.007422 0.176963 0.140990 11.00000 -1.50000 H11C 2 0.243821 0.227685 0.151904 11.00000 -1.50000 AFIX 0 C13 1 0.101882 0.473919 0.212847 11.00000 0.01831 0.03409 = 0.02234 -0.00278 -0.00471 0.00492 C16 1 0.247480 0.617815 0.251681 11.00000 0.01380 0.03029 = 0.02810 0.00167 -0.01000 0.00665 AFIX 23 H16A 2 0.184603 0.561811 0.270056 11.00000 -1.20000 H16B 2 0.135411 0.686681 0.247990 11.00000 -1.20000 AFIX 0 C17 1 0.475114 0.669531 0.263226 11.00000 0.01227 0.03526 = 0.02385 0.00092 -0.00297 0.00477 AFIX 13 H17 2 0.440578 0.736237 0.280851 11.00000 -1.20000 AFIX 0 C18 1 0.598029 0.729849 0.234125 11.00000 0.02897 0.03914 = 0.02868 0.00126 -0.00175 0.00484 AFIX 137 H18A 2 0.736554 0.772287 0.243129 11.00000 -1.50000 H18B 2 0.495466 0.790997 0.222894 11.00000 -1.50000 H18C 2 0.644304 0.666619 0.216881 11.00000 -1.50000 AFIX 0 C20 1 0.569457 0.536508 0.309337 11.00000 0.01831 0.03409 = 0.02234 -0.00278 -0.00471 0.00492 C24 1 0.694978 0.399412 0.353337 11.00000 0.01085 0.05184 = 0.03451 0.00655 -0.00770 -0.00125 AFIX 23 H24A 2 0.577938 0.332582 0.350268 11.00000 -1.20000 H24B 2 0.634113 0.459599 0.370799 11.00000 -1.20000 AFIX 0 C25 1 0.914275 0.344150 0.366660 11.00000 0.01227 0.03526 = 0.02385 0.00092 -0.00297 0.00477 AFIX 13 H25 2 0.878456 0.293676 0.388086 11.00000 -1.20000 AFIX 0 C26 1 1.015449 0.254885 0.337786 11.00000 0.02897 0.03914 = 0.02868 0.00126 -0.00175 0.00484 AFIX 137 H26A 2 0.891594 0.200772 0.328844 11.00000 -1.50000 H26B 2 1.138840 0.203425 0.348021 11.00000 -1.50000 H26C 2 1.079113 0.304698 0.318457 11.00000 -1.50000 AFIX 0 C28 1 1.087333 0.484436 0.406464 11.00000 0.01831 0.03409 = 0.02234 -0.00278 -0.00471 0.00492 C31 1 1.332821 0.625674 0.443352 11.00000 0.04873 0.03320 = 0.02878 0.00005 -0.01078 -0.01377 C32 1 1.506405 0.712971 0.433034 11.00000 0.05165 0.03018 = 0.03968 0.01219 -0.01938 -0.00868 AFIX 137 H32A 2 1.652609 0.668809 0.428649 11.00000 -1.50000 H32B 2 1.529140 0.774399 0.451804 11.00000 -1.50000 H32C 2 1.456938 0.755787 0.411548 11.00000 -1.50000 AFIX 0 C33 1 1.431214 0.540834 0.469821 11.00000 0.05819 0.06752 = 0.04528 0.02035 -0.00954 -0.01006 AFIX 137 H33A 2 1.306540 0.509087 0.484897 11.00000 -1.50000 H33B 2 1.544633 0.586110 0.484178 11.00000 -1.50000 H33C 2 1.508051 0.470754 0.458032 11.00000 -1.50000 AFIX 0 C34 1 1.110977 0.695475 0.459834 11.00000 0.06524 0.07638 = 0.05026 -0.01602 -0.00309 0.00443 AFIX 137 H34A 2 1.059482 0.761550 0.443816 11.00000 -1.50000 H34B 2 1.153271 0.732261 0.482521 11.00000 -1.50000 H34C 2 0.984946 0.635166 0.463211 11.00000 -1.50000 AFIX 0 HKLF 4 REM merge_a.res in P2(1)2(1)2(1) REM wR2 = 0.2955, GooF = S = 1.017, Restrained GooF = 0.977 for all data REM R1 = 0.1245 for 911 Fo > 4sig(Fo) and 0.1917 for all 2001 data REM 216 parameters refined using 224 restraints END WGHT 0.1161 0.0000 REM Highest difference peak 0.117, deepest hole -0.125, 1-sigma level 0.035 Q1 1 -0.2417 0.5822 0.0429 11.00000 0.05 0.12 Q2 1 -0.1822 0.5799 0.0553 11.00000 0.05 0.11 ; _shelx_res_checksum 69866 _shelx_hkl_file ; -1 3 0 414.05 88.73 0 4 0 1686.69 174.69 -1 -1 0 255.66 70.06 -1 0 0 43.82 30.09 -1 1 0 121.02 32.66 0 1 0 -82.00 47.40 -1 2 0 3524.99 148.51 0 2 0 1538.03 128.62 0 3 0 20.33 45.76 -1 -4 0 598.47 78.22 0 -4 0 1273.95 98.95 -2 -3 0 292.90 56.46 -1 -3 0 268.38 64.43 0 -3 0 55.49 52.93 -2 -2 0 1163.55 84.99 0 -2 0 1428.12 99.97 -2 -1 0 180.00 43.16 0 -1 0 9.84 41.49 -2 -8 0 18.48 15.84 -1 -8 0 64.46 21.43 -3 -7 0 14.21 14.63 -2 -7 0 53.46 21.88 -1 -7 0 19.02 23.36 0 -7 0 31.13 24.33 -3 -6 0 39.59 19.63 -2 -6 0 154.18 34.01 0 -6 0 240.17 47.45 -3 -5 0 145.54 29.60 -2 -5 0 94.85 36.14 -1 -5 0 92.58 44.61 0 -5 0 47.32 43.78 1 -5 0 82.60 38.39 -3 -4 0 154.73 32.64 -2 -4 0 496.55 65.00 1 -4 0 677.37 64.85 -3 -3 0 180.57 34.64 1 -3 0 337.91 53.30 -3 -2 0 32.42 24.91 -3 -1 0 70.88 25.21 -2 0 0 169.95 35.68 5 4 -1 9.92 7.36 5 5 -1 2.80 5.52 4 6 -1 14.26 11.61 4 7 -1 8.59 8.14 3 8 -1 6.22 10.22 2 9 -1 8.92 11.06 -1 10 -1 4.97 7.96 0 10 -1 13.03 9.75 0 -10 0 28.58 11.38 1 -10 0 6.62 8.02 -2 -9 0 5.26 11.32 -1 -9 0 7.67 13.74 0 -9 0 2.51 13.45 1 -9 0 5.01 12.93 -3 -8 0 4.65 10.70 0 -8 0 157.04 29.49 1 -8 0 77.80 21.18 -4 -7 0 4.06 7.67 1 -7 0 32.24 21.40 -4 -6 0 6.24 9.76 1 -6 0 493.85 52.52 -5 -5 0 3.39 5.77 -4 -5 0 21.28 13.28 -5 -4 0 15.90 7.65 -4 -4 0 50.24 16.54 -4 -3 0 14.11 13.98 -4 -2 0 23.43 13.66 1 -2 0 3176.23 109.66 -3 0 0 23.33 16.93 5 3 -1 50.47 11.47 4 5 -1 22.52 15.27 3 7 -1 17.43 14.98 1 8 -1 12.77 19.89 2 8 -1 16.18 16.49 -3 9 -1 3.73 5.55 -2 9 -1 14.21 10.57 -1 9 -1 6.36 12.59 0 9 -1 8.24 14.26 1 9 -1 6.72 14.03 2 -9 0 4.07 9.30 2 -8 0 23.39 13.76 2 -7 0 41.12 17.90 2 -6 0 134.40 26.17 2 -5 0 88.07 26.44 2 -4 0 470.31 42.45 -5 -3 0 10.10 8.44 -5 -2 0 2.27 7.74 -4 -1 0 9.16 11.91 5 2 -1 5.71 8.86 4 4 -1 9.75 14.44 3 6 -1 25.65 19.46 2 7 -1 40.81 21.90 -1 8 -1 15.35 16.71 0 8 -1 14.59 18.49 3 -9 0 2.09 5.28 3 -8 0 4.32 8.20 3 -7 0 8.35 10.77 3 -6 0 37.37 13.27 2 -3 0 235.84 31.50 -5 -1 0 7.57 7.79 -4 0 0 10.15 10.08 4 3 -1 24.04 16.10 3 5 -1 278.97 37.07 2 6 -1 20.27 24.31 0 7 -1 42.30 25.69 1 7 -1 15.16 23.97 -3 8 -1 4.64 8.38 -2 8 -1 12.12 13.33 3 -5 0 112.47 18.71 1 -1 0 118.81 21.13 -5 0 0 5.29 7.21 5 1 -1 28.60 9.99 3 4 -1 74.77 28.89 2 5 -1 36.74 30.86 1 6 -1 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-5 0 20.76 11.43 -3 -5 1 225.36 24.18 -2 -5 2 9.01 12.54 -3 -9 4 16.85 13.01 2 -7 7 35.92 15.10 -4 5 -8 13.73 10.43 -3 5 -7 32.07 12.93 -2 5 -6 233.81 26.67 -1 6 -6 38.95 16.71 1 8 -6 34.05 16.11 2 9 -6 4.37 10.93 1 7 -5 10.21 12.95 -3 -1 -2 115.12 8.98 4 4 0 67.96 12.68 -1 -5 3 50.93 18.23 1 -4 4 42.17 16.33 -2 -9 5 10.89 13.92 -1 -9 6 8.45 13.68 1 -8 7 15.54 13.82 3 -7 8 29.38 14.37 4 -6 8 2.49 9.49 -4 6 -9 9.68 10.37 -3 6 -8 73.85 17.16 -2 6 -7 16.22 13.78 -1 7 -7 5.53 12.04 1 9 -7 0.29 11.35 -4 -1 -3 5.12 2.28 4 5 -1 8.11 9.37 3 3 0 120.59 15.28 -4 -6 1 8.23 11.04 -3 -6 2 11.27 12.28 -2 -6 3 16.02 13.25 1 -9 8 20.27 14.98 2 -8 8 11.28 13.19 -4 7 -10 37.41 12.84 -3 8 -10 7.90 11.69 -2 9 -10 39.90 15.86 -3 7 -9 133.45 22.40 -2 8 -9 24.28 14.26 -1 9 -9 14.06 13.34 -2 7 -8 6.14 12.54 -1 8 -8 20.09 13.69 4 6 -2 29.46 11.79 -2 -1 -1 788.42 25.14 2 2 0 958.19 35.98 -1 -6 4 19.27 14.33 1 -5 5 17.44 15.09 2 -4 5 1620.59 64.01 3 -3 5 36.16 11.04 2 -9 9 20.83 14.61 3 -8 9 16.57 13.09 4 -7 9 19.76 11.24 -5 -1 -4 17.95 3.47 4 7 -3 5.18 9.27 3 4 -1 66.95 13.93 1 1 0 106.05 12.02 -4 -7 2 21.74 12.15 -3 -7 3 46.25 16.44 -2 -7 4 67.15 18.16 -1 -7 5 9.40 14.54 4 -2 5 96.05 11.44 3 7 -4 46.55 15.06 3 6 -3 27.42 12.76 3 5 -2 160.14 20.74 2 3 -1 99.27 16.70 -3 -8 4 31.27 15.47 -2 -8 5 9.64 14.00 1 -6 6 41.08 16.15 2 -5 6 244.47 27.19 3 -4 6 13.62 10.62 3 9 -6 4.92 9.27 3 8 -5 7.17 10.88 2 4 -2 189.45 22.43 -1 -1 0 80.45 11.21 -3 -9 5 8.96 12.19 -2 -9 6 10.97 14.00 -1 -8 6 38.36 16.93 4 -3 6 31.29 9.89 1 -7 7 2.31 12.74 2 -6 7 14.16 13.84 2 9 -7 8.63 11.56 2 8 -6 1.26 11.80 2 7 -5 134.18 22.77 2 6 -4 13.90 12.91 2 5 -3 42.78 14.94 -4 -2 -2 26.75 7.68 -3 -2 -1 19.28 8.70 1 2 -1 509.29 26.79 -2 -2 0 978.22 36.62 -1 -9 7 3.17 13.15 3 -5 7 22.83 12.36 1 -8 8 27.09 15.35 2 -7 8 6.14 13.23 1 9 -8 15.28 13.85 1 8 -7 10.63 12.99 1 7 -6 23.56 14.14 1 6 -5 29.82 14.85 1 5 -4 52.38 17.15 -5 -2 -3 43.18 7.55 1 4 -3 55.91 16.30 1 3 -2 53.06 15.72 5 -1 5 61.48 6.94 4 -4 7 7.90 9.31 3 -6 8 71.30 17.12 1 -9 9 8.15 14.12 2 -8 9 32.88 16.71 -3 8 -11 33.94 14.70 -2 9 -11 14.64 13.58 -2 8 -10 43.83 17.45 -1 9 -10 22.79 15.08 -1 8 -9 5.79 12.43 -1 7 -8 8.03 14.12 -4 -3 -1 29.70 9.83 -3 -3 0 134.56 16.71 -2 -3 1 109.93 17.86 -1 -2 1 474.85 26.10 4 -5 8 15.47 11.05 3 -7 9 123.42 22.10 2 -9 10 34.49 15.96 3 -8 10 6.92 12.36 -4 7 -11 10.65 10.81 -4 6 -10 18.96 11.82 -3 7 -10 66.95 19.05 -3 6 -9 29.64 14.36 -2 7 -9 14.84 14.38 -2 6 -8 12.85 14.09 -1 6 -7 12.77 13.77 -1 5 -6 75.62 19.68 -5 -3 -2 114.67 13.91 -5 -4 -1 10.43 9.22 5 5 -1 3.41 7.24 -4 -4 0 66.64 14.02 -4 -5 1 7.97 11.57 -3 -4 1 55.88 14.36 -3 -5 2 155.38 21.92 -2 -4 2 141.02 21.15 -1 -3 2 50.37 16.07 -2 -5 3 52.35 16.72 5 -2 6 18.54 7.00 5 -3 7 10.73 7.54 4 -6 9 8.82 10.73 4 -7 10 35.42 13.54 -5 4 -9 37.50 11.07 -4 5 -9 31.48 12.83 -5 3 -8 7.42 7.87 -4 4 -8 37.51 12.19 -3 5 -8 15.51 12.44 -3 4 -7 12.24 11.10 -2 5 -7 148.75 22.97 -2 4 -6 687.34 41.15 -1 4 -5 21.41 15.53 -1 3 -4 44.77 15.37 4 7 -4 15.12 10.92 -5 -5 0 9.58 9.58 5 4 0 37.10 10.12 5 3 1 53.72 10.39 -4 -6 2 30.73 14.10 -4 -7 3 7.67 12.16 -3 -6 3 36.85 15.50 -1 -4 3 62.30 17.93 -3 -7 4 68.33 19.55 -2 -6 4 7.27 13.89 -1 -5 4 51.95 18.23 -2 -7 5 133.46 24.20 -1 -6 5 24.27 16.83 5 -4 8 12.67 8.45 2 9 -8 8.09 13.46 -5 2 -7 8.95 6.48 -4 3 -7 134.97 16.77 -3 3 -6 22.85 11.19 3 8 -6 0.32 12.27 -2 3 -5 443.62 30.52 -1 2 -3 184.12 19.58 4 6 -3 4.26 10.41 5 2 2 30.04 5.80 -3 -8 5 8.67 13.89 -3 -9 6 3.15 13.87 -2 -8 6 2.53 14.87 -1 -7 6 19.83 15.51 -2 -9 7 6.22 14.39 -1 -8 7 15.51 15.78 -1 -9 8 25.82 18.47 1 9 -9 1.49 13.14 2 8 -7 9.40 13.74 -4 2 -6 53.30 10.04 3 7 -5 16.51 14.32 -2 2 -4 300.20 21.90 4 5 -2 90.34 17.26 1 -3 4 51.09 16.39 1 -4 5 18.75 16.53 1 -5 6 76.17 20.43 1 -6 7 11.22 14.83 1 -7 8 8.14 14.53 1 -8 9 7.52 16.19 -2 9 -12 8.63 14.51 -1 9 -11 8.70 14.52 1 8 -8 14.14 14.91 -5 1 -6 43.46 6.77 2 7 -6 42.85 17.15 -3 2 -5 215.08 18.24 3 6 -4 31.00 14.69 -1 1 -2 91.95 12.70 4 4 -1 8.88 9.63 1 -2 3 156.89 19.11 2 -7 9 27.90 16.45 1 -9 10 24.95 17.77 2 -8 10 33.42 18.78 -2 8 -11 101.05 23.96 -1 8 -10 1.22 13.63 1 7 -7 2.97 13.44 2 6 -5 12.42 13.81 3 5 -3 21.57 13.74 5 1 3 25.38 4.38 2 -4 6 723.34 43.71 2 -5 7 166.44 25.02 2 -6 8 5.25 14.14 2 -9 11 16.62 15.98 -3 8 -12 11.88 14.10 -1 7 -9 10.73 16.41 1 6 -6 26.97 17.64 -4 1 -5 19.47 5.19 4 3 0 12.12 8.77 2 -3 5 499.81 33.29 3 -6 9 29.89 16.10 3 -7 10 63.29 20.62 3 -8 11 32.80 16.88 -3 7 -11 55.97 20.08 -2 7 -10 23.28 17.09 -3 1 -4 239.50 14.99 2 5 -4 198.42 26.62 -2 1 -3 23.98 9.02 3 4 -2 47.01 14.24 1 -1 2 80.79 12.93 3 -4 7 10.26 12.04 3 -5 8 24.28 14.33 4 -7 11 21.20 13.93 -4 6 -11 5.43 12.51 -3 6 -10 53.21 18.80 -2 6 -9 75.61 20.67 2 9 -9 17.99 16.22 -1 6 -8 33.87 17.98 3 8 -7 8.04 14.40 1 5 -5 20.77 17.27 4 7 -5 14.20 13.10 2 -2 4 289.57 22.46 -3 -8 6 1.69 16.82 -2 -8 7 9.85 17.14 -2 -9 8 9.74 17.09 -1 -8 8 9.22 18.49 -1 -9 9 8.60 17.07 4 -6 10 18.82 13.99 1 9 -10 23.41 17.99 2 8 -8 9.75 16.57 2 4 -3 33.35 16.65 3 3 -1 215.73 21.67 4 2 1 11.74 7.48 -4 -6 3 6.07 14.73 -4 -7 4 11.43 14.87 -3 -6 4 37.91 18.02 -3 -7 5 12.80 16.78 -2 -6 5 6.32 15.62 -2 -7 6 48.97 20.85 3 -3 6 24.74 12.28 -1 -7 7 2.26 15.53 4 -5 9 27.97 14.39 1 -9 11 4.98 16.76 -2 9 -13 6.15 15.75 -1 9 -12 29.76 19.82 -4 5 -10 30.53 15.76 -3 5 -9 22.15 15.33 1 8 -9 5.76 16.16 -2 5 -8 20.55 16.51 -1 5 -7 84.49 22.36 3 7 -6 44.27 18.84 4 6 -4 15.87 14.44 5 5 -2 1.03 9.34 -1 -6 6 26.19 17.44 4 -4 8 34.22 14.07 1 -7 9 6.30 17.61 1 -8 10 -0.90 16.32 2 -9 12 6.43 16.53 -3 8 -13 4.60 15.23 -2 8 -12 7.67 17.29 -1 8 -11 2.97 16.62 2 7 -7 26.78 18.60 1 4 -4 50.39 18.78 -5 -5 1 6.06 12.56 -4 -5 2 85.92 20.64 -3 -5 3 24.37 15.99 -2 -5 4 183.36 27.44 -1 -5 5 17.38 17.76 1 -6 8 32.36 19.61 2 -7 10 22.49 18.34 2 -8 11 97.73 26.93 -5 4 -10 4.15 11.01 1 7 -8 5.36 15.66 3 6 -5 30.46 17.16 2 3 -2 37.45 15.23 -3 -4 2 49.47 16.23 3 -2 5 211.48 19.48 4 -3 7 118.71 18.30 3 -8 12 12.61 16.78 -1 7 -10 26.44 19.39 2 9 -10 27.95 21.52 -4 4 -9 8.76 13.39 -3 4 -8 27.23 14.79 -2 4 -7 975.15 53.85 -1 4 -6 100.45 23.14 4 5 -3 134.30 23.93 -4 -4 1 10.94 12.98 -2 -4 3 24.99 17.00 2 -1 3 22.62 9.34 -1 -4 4 50.23 18.85 1 -5 7 86.13 23.22 -2 -9 9 24.63 23.70 2 -6 9 72.70 21.97 5 -4 9 31.18 13.83 3 -7 11 80.29 25.10 -3 7 -12 12.26 17.99 -2 7 -11 8.25 18.21 1 9 -11 4.65 18.31 3 8 -8 24.08 20.03 2 6 -6 73.50 21.67 5 4 -1 3.81 11.17 -5 -4 0 55.15 16.51 3 2 0 5.37 9.70 -3 -8 7 4.03 20.05 -2 -8 8 7.07 21.49 2 -5 8 19.79 17.71 -1 -9 10 22.71 22.94 3 -6 10 54.07 21.37 -2 9 -14 15.17 20.07 -1 9 -13 0.42 18.50 0 9 -12 7.19 18.40 2 8 -9 24.93 22.76 1 6 -7 12.69 18.51 3 5 -4 49.76 18.36 1 3 -3 97.94 20.08 1 -4 6 95.09 22.71 -1 -8 9 5.03 19.96 1 -9 12 31.20 23.94 2 -9 13 6.94 21.58 -4 6 -12 12.67 17.24 -3 6 -11 103.55 26.11 -2 6 -10 28.02 21.07 1 8 -10 0.47 18.53 -5 3 -9 3.17 11.53 -1 6 -9 94.84 24.68 4 7 -6 5.80 15.87 -4 -3 0 8.75 11.73 -3 -3 1 208.22 22.69 -2 -3 2 39.30 15.81 -4 -7 5 14.98 20.13 -3 -7 6 61.59 24.94 -2 -7 7 26.25 21.85 -1 -7 8 7.32 18.58 5 -3 8 5.55 11.01 3 -5 9 27.15 18.21 1 -8 11 6.86 19.46 4 -6 11 8.80 16.70 -3 8 -14 6.72 19.90 -2 8 -13 2.78 21.31 -1 8 -12 16.83 21.20 0 8 -11 0.80 17.06 -4 3 -8 66.96 16.91 3 7 -7 29.76 21.11 -1 3 -5 460.64 33.57 2 5 -5 105.01 23.98 4 4 -2 22.13 14.36 -1 -3 3 93.90 19.98 4 -2 6 46.07 11.52 2 -4 7 999.26 55.24 1 -7 10 20.34 21.85 2 -8 12 15.94 22.59 2 7 -8 4.08 18.17 -3 3 -7 6.87 12.72 -2 3 -6 93.05 20.55 1 5 -6 75.57 22.73 -5 -3 -1 73.86 16.25 -4 -6 4 18.08 20.23 -3 -6 5 31.59 21.14 -2 -6 6 68.26 23.91 -1 -6 7 14.93 19.28 4 -5 10 34.94 19.40 2 -7 11 11.31 20.48 3 -8 13 6.98 19.58 1 9 -12 18.18 25.18 -4 5 -11 5.92 17.99 2 9 -11 14.16 23.68 1 7 -9 6.30 18.55 -1 5 -8 110.27 27.20 4 6 -5 1.89 17.51 3 4 -3 83.60 19.33 2 2 -1 64.30 13.83 5 3 0 7.95 10.07 4 1 2 2.75 3.82 3 -4 8 28.99 16.32 -2 -9 10 44.28 28.92 -1 -9 11 7.39 25.03 -2 9 -15 5.38 26.27 -1 9 -14 2.66 24.80 -3 7 -13 7.23 23.58 0 9 -13 3.17 21.33 -2 7 -12 20.11 23.87 -1 7 -11 3.26 19.11 -3 5 -10 35.14 19.67 0 7 -10 4.95 17.93 -2 5 -9 4.86 17.14 3 8 -9 15.78 24.47 3 6 -6 5.51 17.93 5 5 -3 2.32 11.79 1 -3 5 437.04 32.92 -3 -8 8 34.90 28.62 1 -6 9 89.38 27.02 3 -7 12 26.29 23.47 1 -9 13 3.94 25.16 2 8 -10 26.00 25.14 2 4 -4 165.87 26.30 -4 -5 3 153.94 29.30 -3 -5 4 42.79 19.11 3 -1 4 236.96 17.37 -2 -5 5 99.30 25.05 -1 -5 6 64.53 22.96 -2 -8 9 32.53 29.92 -1 -8 10 4.21 23.86 2 -6 10 47.74 23.29 2 -9 14 20.44 27.50 1 8 -11 4.29 20.01 2 6 -7 11.03 17.55 4 7 -7 16.80 19.19 1 2 -2 203.12 20.33 -5 -5 2 -0.35 14.17 2 -3 6 98.15 19.80 5 -2 7 6.28 8.10 4 -4 9 10.43 13.76 3 -6 11 99.05 27.59 1 -8 12 18.41 23.86 -3 8 -15 7.55 21.15 -2 8 -14 2.37 21.19 -4 6 -13 18.47 19.07 -1 8 -13 7.91 20.58 0 8 -12 1.48 17.70 -5 4 -11 8.88 12.84 0 6 -9 3.62 15.34 -5 2 -8 5.03 7.67 1 6 -8 26.95 19.49 1 4 -5 18.94 16.21 4 5 -4 208.53 33.67 4 3 -1 6.85 9.30 -3 -2 0 4.47 7.01 -2 -2 1 66.38 14.78 -4 -7 6 7.99 18.71 -3 -7 7 25.59 23.74 -2 -7 8 1.44 20.18 1 -5 8 83.40 23.53 -1 -7 9 13.95 19.69 2 -8 13 0.40 22.03 -3 6 -12 53.30 22.72 2 9 -12 1.92 20.18 -2 6 -11 169.75 34.79 -4 4 -10 39.61 16.30 -1 6 -10 16.35 16.41 3 7 -8 22.31 21.27 -1 4 -7 10.35 12.13 -4 -2 -1 19.60 7.88 -1 -2 2 209.23 24.84 3 -3 7 3.17 8.58 2 -5 9 3.00 13.28 5 -4 10 12.56 11.45 -2 -9 11 14.26 22.57 1 -7 11 10.37 15.52 -1 -9 12 34.75 26.97 4 -6 12 7.87 16.41 3 -8 14 10.51 20.78 1 9 -13 3.65 44.37 -3 4 -9 58.54 31.83 -2 4 -8 135.95 41.92 -4 2 -7 120.46 28.49 3 5 -5 90.64 40.28 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 48953 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.826(3) 0.545(3) 0.0768(9) 0.080(10) Uani 1 1 d D . . . . H1 H -0.771283 0.566080 0.096334 0.120 Uiso 1 1 calc R U . . . O7 O -0.554(3) 0.5145(16) 0.1298(9) 0.042(7) Uani 1 1 d . . . . . O8 O -0.194(3) 0.4574(15) 0.1289(9) 0.029(2) Uani 1 1 d . . . . . O14 O -0.044(3) 0.4466(15) 0.2334(8) 0.028(5) Uani 1 1 d . . . . . O15 O 0.277(3) 0.5515(15) 0.2205(9) 0.029(2) Uani 1 1 d . . . . . O21 O 0.395(3) 0.5619(17) 0.3284(9) 0.038(6) Uani 1 1 d . . . . . O22 O 0.729(3) 0.4604(15) 0.3213(9) 0.029(2) Uani 1 1 d . . . . . O29 O 0.985(3) 0.441(2) 0.4334(10) 0.047(6) Uani 1 1 d . . . . . O30 O 1.252(2) 0.5703(15) 0.4115(8) 0.029(2) Uani 1 1 d . . . . . N5 N -0.309(3) 0.5687(15) 0.0859(8) 0.024(2) Uani 1 1 d . . . . . H5 H -0.167829 0.557293 0.077497 0.029 Uiso 1 1 calc R U . . . N12 N 0.142(3) 0.4198(15) 0.1858(9) 0.024(2) Uani 1 1 d . . . . . H12 H 0.270853 0.437904 0.174540 0.029 Uiso 1 1 calc R U . . . N19 N 0.614(3) 0.5788(15) 0.2806(9) 0.024(2) Uani 1 1 d . . . . . H19 H 0.739022 0.551715 0.269780 0.029 Uiso 1 1 calc R U . . . N27 N 1.080(3) 0.4327(15) 0.3753(9) 0.024(2) Uani 1 1 d . . . . . H27 H 1.183503 0.454809 0.359425 0.029 Uiso 1 1 calc R U . . . C2 C -0.665(3) 0.578(2) 0.0493(9) 0.051(7) Uani 1 1 d D . . . . H2A H -0.740641 0.633546 0.031991 0.061 Uiso 1 1 calc R U . . . H2B H -0.610356 0.501925 0.036929 0.061 Uiso 1 1 calc R U . . . C3 C -0.460(3) 0.6448(17) 0.0670(8) 0.024(3) Uani 1 1 d D . . . . H3 H -0.514451 0.717099 0.081463 0.029 Uiso 1 1 calc R U . . . C4 C -0.317(3) 0.6899(17) 0.0341(8) 0.032(3) Uani 1 1 d D . . . . H4A H -0.413729 0.744358 0.019521 0.048 Uiso 1 1 calc R U . . . H4B H -0.179515 0.736239 0.042031 0.048 Uiso 1 1 calc R U . . . H4C H -0.267485 0.617314 0.020328 0.048 Uiso 1 1 calc R U . . . C6 C -0.361(3) 0.5147(17) 0.1147(10) 0.025(2) Uani 1 1 d . . . . . C9 C -0.232(3) 0.3789(16) 0.1590(9) 0.026(5) Uani 1 1 d . . . . . H9A H -0.341709 0.311321 0.152879 0.031 Uiso 1 1 calc R U . . . H9B H -0.300569 0.428708 0.178267 0.031 Uiso 1 1 calc R U . . . C10 C -0.013(3) 0.3251(17) 0.1706(9) 0.024(3) Uani 1 1 d . . . . . H10 H -0.053293 0.266852 0.190208 0.029 Uiso 1 1 calc R U . . . C11 C 0.087(3) 0.2520(17) 0.1446(9) 0.032(3) Uani 1 1 d . . . . . H11A H 0.095300 0.299678 0.122710 0.048 Uiso 1 1 calc R U . . . H11B H -0.007422 0.176963 0.140990 0.048 Uiso 1 1 calc R U . . . H11C H 0.243821 0.227685 0.151904 0.048 Uiso 1 1 calc R U . . . C13 C 0.102(3) 0.4739(17) 0.2128(10) 0.025(2) Uani 1 1 d . . . . . C16 C 0.247(3) 0.6178(16) 0.2517(9) 0.024(5) Uani 1 1 d . . . . . H16A H 0.184603 0.561811 0.270056 0.029 Uiso 1 1 calc R U . . . H16B H 0.135411 0.686681 0.247990 0.029 Uiso 1 1 calc R U . . . C17 C 0.475(3) 0.6695(18) 0.2632(9) 0.024(3) Uani 1 1 d . . . . . H17 H 0.440578 0.736237 0.280851 0.029 Uiso 1 1 calc R U . . . C18 C 0.598(3) 0.7298(17) 0.2341(9) 0.032(3) Uani 1 1 d . . . . . H18A H 0.736554 0.772287 0.243129 0.048 Uiso 1 1 calc R U . . . H18B H 0.495466 0.790997 0.222894 0.048 Uiso 1 1 calc R U . . . H18C H 0.644304 0.666619 0.216881 0.048 Uiso 1 1 calc R U . . . C20 C 0.569(3) 0.5365(17) 0.3093(10) 0.025(2) Uani 1 1 d . . . . . C24 C 0.695(3) 0.3994(18) 0.3533(10) 0.032(5) Uani 1 1 d . . . . . H24A H 0.577938 0.332582 0.350268 0.039 Uiso 1 1 calc R U . . . H24B H 0.634113 0.459599 0.370799 0.039 Uiso 1 1 calc R U . . . C25 C 0.914(3) 0.3441(16) 0.3667(9) 0.024(3) Uani 1 1 d . . . . . H25 H 0.878456 0.293676 0.388086 0.029 Uiso 1 1 calc R U . . . C26 C 1.015(3) 0.2549(16) 0.3378(9) 0.032(3) Uani 1 1 d . . . . . H26A H 0.891594 0.200772 0.328844 0.048 Uiso 1 1 calc R U . . . H26B H 1.138840 0.203425 0.348021 0.048 Uiso 1 1 calc R U . . . H26C H 1.079113 0.304698 0.318457 0.048 Uiso 1 1 calc R U . . . C28 C 1.087(3) 0.4844(18) 0.4065(10) 0.025(2) Uani 1 1 d . . . . . C31 C 1.333(4) 0.6257(18) 0.4434(10) 0.037(5) Uani 1 1 d . . . . . C32 C 1.506(3) 0.7130(16) 0.4330(10) 0.041(7) Uani 1 1 d . . . . . H32A H 1.652609 0.668809 0.428649 0.061 Uiso 1 1 calc R U . . . H32B H 1.529140 0.774399 0.451804 0.061 Uiso 1 1 calc R U . . . H32C H 1.456938 0.755787 0.411548 0.061 Uiso 1 1 calc R U . . . C33 C 1.431(4) 0.541(2) 0.4698(10) 0.057(7) Uani 1 1 d . . . . . H33A H 1.306540 0.509087 0.484897 0.085 Uiso 1 1 calc R U . . . H33B H 1.544633 0.586110 0.484178 0.085 Uiso 1 1 calc R U . . . H33C H 1.508051 0.470754 0.458032 0.085 Uiso 1 1 calc R U . . . C34 C 1.111(4) 0.695(2) 0.4598(11) 0.064(8) Uani 1 1 d . . . . . H34A H 1.059482 0.761550 0.443816 0.096 Uiso 1 1 calc R U . . . H34B H 1.153271 0.732261 0.482521 0.096 Uiso 1 1 calc R U . . . H34C H 0.984946 0.635166 0.463211 0.096 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.040(10) 0.116(19) 0.09(2) 0.02(2) -0.001(14) -0.004(10) O7 0.032(7) 0.060(11) 0.035(17) 0.029(12) 0.002(9) 0.016(7) O8 0.024(3) 0.035(4) 0.029(6) -0.002(4) -0.007(4) 0.004(3) O14 0.025(7) 0.036(8) 0.024(12) -0.005(9) -0.001(8) 0.003(6) O15 0.024(3) 0.035(4) 0.029(6) -0.002(4) -0.007(4) 0.004(3) O21 0.030(7) 0.059(10) 0.024(14) 0.006(11) 0.002(9) 0.012(7) O22 0.024(3) 0.035(4) 0.029(6) -0.002(4) -0.007(4) 0.004(3) O29 0.045(10) 0.063(10) 0.034(11) -0.003(9) 0.006(9) -0.014(9) O30 0.024(3) 0.035(4) 0.029(6) -0.002(4) -0.007(4) 0.004(3) N5 0.015(3) 0.033(3) 0.024(6) -0.002(4) -0.006(4) 0.004(3) N12 0.015(3) 0.033(3) 0.024(6) -0.002(4) -0.006(4) 0.004(3) N19 0.015(3) 0.033(3) 0.024(6) -0.002(4) -0.006(4) 0.004(3) N27 0.015(3) 0.033(3) 0.024(6) -0.002(4) -0.006(4) 0.004(3) C2 0.035(8) 0.063(12) 0.055(17) 0.005(12) -0.021(9) -0.011(8) C3 0.012(3) 0.035(4) 0.024(6) 0.001(4) -0.003(4) 0.005(3) C4 0.029(5) 0.039(4) 0.029(7) 0.001(5) -0.002(5) 0.005(4) C6 0.018(3) 0.034(4) 0.022(6) -0.003(4) -0.005(4) 0.005(3) C9 0.020(7) 0.030(8) 0.028(11) -0.001(8) -0.013(7) 0.003(5) C10 0.012(3) 0.035(4) 0.024(6) 0.001(4) -0.003(4) 0.005(3) C11 0.029(5) 0.039(4) 0.029(7) 0.001(5) -0.002(5) 0.005(4) C13 0.018(3) 0.034(4) 0.022(6) -0.003(4) -0.005(4) 0.005(3) C16 0.014(6) 0.030(9) 0.028(11) 0.002(8) -0.010(6) 0.007(5) C17 0.012(3) 0.035(4) 0.024(6) 0.001(4) -0.003(4) 0.005(3) C18 0.029(5) 0.039(4) 0.029(7) 0.001(5) -0.002(5) 0.005(4) C20 0.018(3) 0.034(4) 0.022(6) -0.003(4) -0.005(4) 0.005(3) C24 0.011(7) 0.052(10) 0.035(11) 0.007(8) -0.008(7) -0.001(6) C25 0.012(3) 0.035(4) 0.024(6) 0.001(4) -0.003(4) 0.005(3) C26 0.029(5) 0.039(4) 0.029(7) 0.001(5) -0.002(5) 0.005(4) C28 0.018(3) 0.034(4) 0.022(6) -0.003(4) -0.005(4) 0.005(3) C31 0.049(9) 0.033(8) 0.029(11) 0.000(8) -0.011(8) -0.014(6) C32 0.052(10) 0.030(9) 0.04(2) 0.012(11) -0.019(11) -0.009(7) C33 0.058(12) 0.068(12) 0.045(16) 0.020(12) -0.010(12) -0.010(10) C34 0.065(11) 0.076(13) 0.05(2) -0.016(14) -0.003(12) 0.004(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 109.5 . . ? C6 O8 C9 121(2) . . ? C13 O15 C16 114(2) . . ? C20 O22 C24 120(2) . . ? C28 O30 C31 130(3) . . ? C3 N5 H5 117.9 . . ? C6 N5 H5 117.9 . . ? C6 N5 C3 124(2) . . ? C10 N12 H12 118.2 . . ? C13 N12 H12 118.2 . . ? C13 N12 C10 124(2) . . ? C17 N19 H19 118.0 . . ? C20 N19 H19 118.0 . . ? C20 N19 C17 124(2) . . ? C25 N27 H27 119.2 . . ? C28 N27 H27 119.1 . . ? C28 N27 C25 122(3) . . ? O1 C2 H2A 110.4 . . ? O1 C2 H2B 110.4 . . ? O1 C2 C3 107(2) . . ? H2A C2 H2B 108.6 . . ? C3 C2 H2A 110.4 . . ? C3 C2 H2B 110.4 . . ? N5 C3 C2 115.7(16) . . ? N5 C3 H3 111.3 . . ? N5 C3 C4 105.1(17) . . ? C2 C3 H3 111.3 . . ? C2 C3 C4 101(2) . . ? C4 C3 H3 111.3 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O7 C6 O8 118(3) . . ? O7 C6 N5 127(3) . . ? O8 C6 N5 114(2) . . ? O8 C9 H9A 109.6 . . ? O8 C9 H9B 109.6 . . ? O8 C9 C10 110(2) . . ? H9A C9 H9B 108.1 . . ? C10 C9 H9A 109.6 . . ? C10 C9 H9B 109.6 . . ? N12 C10 H10 106.0 . . ? C9 C10 N12 111.8(15) . . ? C9 C10 H10 106.0 . . ? C11 C10 N12 114.7(18) . . ? C11 C10 C9 112(3) . . ? C11 C10 H10 106.0 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O14 C13 O15 123(3) . . ? O14 C13 N12 126(2) . . ? N12 C13 O15 110(3) . . ? O15 C16 H16A 109.8 . . ? O15 C16 H16B 109.8 . . ? O15 C16 C17 109(2) . . ? H16A C16 H16B 108.2 . . ? C17 C16 H16A 109.8 . . ? C17 C16 H16B 109.8 . . ? N19 C17 C16 112.2(16) . . ? N19 C17 H17 106.8 . . ? N19 C17 C18 112.4(18) . . ? C16 C17 H17 106.8 . . ? C18 C17 C16 111(3) . . ? C18 C17 H17 106.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O21 C20 O22 119(3) . . ? N19 C20 O21 127(3) . . ? N19 C20 O22 114(3) . . ? O22 C24 H24A 109.4 . . ? O22 C24 H24B 109.4 . . ? O22 C24 C25 111(2) . . ? H24A C24 H24B 108.0 . . ? C25 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? N27 C25 C24 113.3(16) . . ? N27 C25 H25 108.6 . . ? N27 C25 C26 109.1(18) . . ? C24 C25 H25 108.6 . . ? C24 C25 C26 109(2) . . ? C26 C25 H25 108.6 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O29 C28 O30 118(3) . . ? O29 C28 N27 124(2) . . ? N27 C28 O30 116(3) . . ? O30 C31 C33 117(2) . . ? O30 C31 C34 105(2) . . ? C32 C31 O30 106(3) . . ? C32 C31 C33 109(2) . . ? C32 C31 C34 111.1(17) . . ? C33 C31 C34 109(3) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32B 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34B 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1 0.8400 . ? O1 C2 1.44(2) . ? O7 C6 1.25(3) . ? O8 C6 1.26(3) . ? O8 C9 1.44(4) . ? O14 C13 1.19(3) . ? O15 C13 1.34(3) . ? O15 C16 1.39(4) . ? O21 C20 1.27(4) . ? O22 C20 1.31(3) . ? O22 C24 1.40(4) . ? O29 C28 1.27(4) . ? O30 C28 1.33(3) . ? O30 C31 1.43(4) . ? N5 H5 0.8800 . ? N5 C3 1.40(3) . ? N5 C6 1.27(4) . ? N12 H12 0.8800 . ? N12 C10 1.47(3) . ? N12 C13 1.20(4) . ? N19 H19 0.8800 . ? N19 C17 1.42(3) . ? N19 C20 1.21(4) . ? N27 H27 0.8800 . ? N27 C25 1.39(2) . ? N27 C28 1.31(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.54(3) . ? C3 H3 1.0000 . ? C3 C4 1.58(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.45(3) . ? C10 H10 1.0000 . ? C10 C11 1.39(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.49(3) . ? C17 H17 1.0000 . ? C17 C18 1.46(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C24 C25 1.48(3) . ? C25 H25 1.0000 . ? C25 C26 1.57(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C31 C32 1.42(3) . ? C31 C33 1.47(4) . ? C31 C34 1.61(3) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 N5 74(3) . . . . ? O1 C2 C3 C4 -173(2) . . . . ? O8 C9 C10 N12 69(3) . . . . ? O8 C9 C10 C11 -61(2) . . . . ? O15 C16 C17 N19 -80(3) . . . . ? O15 C16 C17 C18 47(2) . . . . ? O22 C24 C25 N27 66(4) . . . . ? O22 C24 C25 C26 -56(2) . . . . ? C3 N5 C6 O7 4(5) . . . . ? C3 N5 C6 O8 -175(2) . . . . ? C6 O8 C9 C10 -179(2) . . . . ? C6 N5 C3 C2 -70(4) . . . . ? C6 N5 C3 C4 180(2) . . . . ? C9 O8 C6 O7 9(4) . . . . ? C9 O8 C6 N5 -172(2) . . . . ? C10 N12 C13 O14 12(4) . . . . ? C10 N12 C13 O15 178.2(19) . . . . ? C13 O15 C16 C17 162.8(18) . . . . ? C13 N12 C10 C9 67(4) . . . . ? C13 N12 C10 C11 -165(3) . . . . ? C16 O15 C13 O14 -13(3) . . . . ? C16 O15 C13 N12 -179(2) . . . . ? C17 N19 C20 O21 2(4) . . . . ? C17 N19 C20 O22 -176(2) . . . . ? C20 O22 C24 C25 -165.6(19) . . . . ? C20 N19 C17 C16 -70(4) . . . . ? C20 N19 C17 C18 164(3) . . . . ? C24 O22 C20 O21 6(3) . . . . ? C24 O22 C20 N19 -176(2) . . . . ? C25 N27 C28 O29 17(3) . . . . ? C25 N27 C28 O30 -178.7(16) . . . . ? C28 O30 C31 C32 -178.9(18) . . . . ? C28 O30 C31 C33 60(3) . . . . ? C28 O30 C31 C34 -61(3) . . . . ? C28 N27 C25 C24 87(3) . . . . ? C28 N27 C25 C26 -152(2) . . . . ? C31 O30 C28 O29 -1(3) . . . . ? C31 O30 C28 N27 -167(2) . . . . ?