#------------------------------------------------------------------------------ #$Date: 2021-05-13 07:03:54 +0300 (Thu, 13 May 2021) $ #$Revision: 265167 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/28/7242821.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_7242821 loop_ _publ_author_name 'Sekharan, Sivakumar' 'Liu, Xuetao' 'Yang, Zhuocen' 'Liu, Xiang' 'Deng, Li' 'Ruan, Shigang' 'Abramov, Yuriy' 'Sun, GuangXu' 'Li, Sizhu' 'Zhou, Tian' 'Shi, Baime' 'Zeng, Qun' 'Zeng, Qiao' 'Chang, Chao' 'Jin, Yingdi' 'Shi, Xuekun' _publ_section_title ; Selecting a stable solid form of remdesivir using microcrystal electron diffraction and crystal structure prediction ; _journal_issue 28 _journal_name_full 'RSC Advances' _journal_page_first 17408 _journal_page_last 17412 _journal_paper_doi 10.1039/D1RA03100G _journal_volume 11 _journal_year 2021 _chemical_formula_sum 'C27 H35 N6 O8 P' _chemical_formula_weight 602.56 _chemical_name_systematic remdesivir _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-02-07 deposited with the CCDC. 2021-04-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.4(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.03(7) _cell_length_b 12.2(2) _cell_length_c 11.44(18) _cell_measurement_temperature 293(2) _cell_volume 1356(3) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 80(2) _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.969 _diffrn_radiation_wavelength 0.02508 _diffrn_reflns_av_R_equivalents 0.4016 _diffrn_reflns_av_unetI/netI 0.2907 _diffrn_reflns_Laue_measured_fraction_full 0.969 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 19547 _diffrn_reflns_point_group_measured_fraction_full 0.960 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 0.752 _diffrn_reflns_theta_max 0.752 _diffrn_reflns_theta_min 0.074 _exptl_absorpt_coefficient_mu 0.000 _exptl_crystal_density_diffrn 1.476 _exptl_crystal_F_000 235 _refine_diff_density_max 0.171 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.050 _refine_ls_abs_structure_details ; All f" are zero, so absolute structure could not be determined ; _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 360 _refine_ls_number_reflns 3133 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.2346 _refine_ls_R_factor_gt 0.1592 _refine_ls_shift/su_max 0.916 _refine_ls_shift/su_mean 0.018 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2209P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3599 _refine_ls_wR_factor_ref 0.4041 _reflns_Friedel_coverage 0.872 _reflns_Friedel_fraction_full 0.949 _reflns_Friedel_fraction_max 0.949 _reflns_number_gt 1639 _reflns_number_total 3133 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra03100g2.cif _cod_data_source_block Remdesivir_formIV_raw _cod_original_cell_volume 1356(33) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7242821 _shelx_shelxl_version_number 2018/3 _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. ; _shelx_res_file ; TITL Remdesivir form 4 in P2(1) Remdesivir_formIV_raw.res created by SHELXL-2018/3 at 15:50:01 on 26-Oct-2020 CELL 0.02508 10.0300 12.2000 11.4400 90.000 104.377 90.000 ZERR 2.000 0.0700 0.2100 0.1800 0.000 0.700 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C 0.7307 36.9951 1.1951 11.2966 0.4563 2.8139 0.1247 0.3456 = 0.0 0.0 0.0 0.0 0.77 12.01 SFAC H 0.3754 15.4946 0.1408 4.1261 0.0216 0.0246 -0.1012 46.884 = 0.0 0.0 0.0 0.0 0.32 1.008 SFAC N 0.5717 28.8465 1.0425 9.0542 0.4647 2.4213 0.1311 0.3167 = 0.0 0.0 0.0 0.0 0.75 14.007 SFAC O 0.4548 23.7803 0.9173 7.622 0.4719 2.144 0.1384 0.2959 = 0.0 0.0 0.0 0.0 0.73 15.999 SFAC P 1.8882 44.8756 2.4685 13.5383 0.8046 2.6454 0.3204 0.3608 = 0.0 0.0 0.0 0.0 1.8 30.974 UNIT 54 70 12 16 2 DFIX 1.54 0.02 C00U C00W C00U C10 C00W C010 C010 C00R C00X C00W DFIX 2.60 0.02 C00W C10 C00W C00R L.S. 10 BOND LIST 6 FMAP 2 PLAN 20 EQIV $1 x-1, y, z HTAB N2 O2_$1 EQIV $2 -x+1, y+1/2, -z+1 HTAB N2 O004_$2 EQIV $3 x+1, y, z HTAB O00T N00D_$3 EQIV $4 x, y+1, z HTAB O2 O3_$4 ACTA CONF WGHT 0.220900 FVAR 1.51700 AFIX 66 N3 3 0.340751 0.837375 0.272204 11.00000 0.08550 0.07490 = 0.02064 -0.00374 -0.02224 0.01566 C00C 1 0.270935 0.849470 0.362271 11.00000 0.08719 0.06843 = 0.07599 0.02005 0.01771 0.01572 C5 1 0.127957 0.853256 0.332374 11.00000 0.02295 0.04831 = 0.09985 -0.02060 0.03562 0.01514 N00D 3 0.054794 0.844945 0.212411 11.00000 0.04471 0.09743 = 0.05524 0.00336 -0.01601 -0.00802 C6 1 0.124608 0.832849 0.122343 11.00000 0.09576 0.15625 = 0.00523 -0.01000 0.01786 0.01614 AFIX 43 H6 2 0.075657 0.827289 0.042080 11.00000 -1.20000 AFIX 65 N5 3 0.267586 0.829064 0.152238 11.00000 0.02883 0.11039 = 0.15308 0.02374 0.06730 0.00555 AFIX 66 C00F 1 1.052918 0.464617 0.229395 11.00000 0.04968 0.11652 = 0.16184 0.07774 0.01290 -0.02039 C1 1 1.079366 0.509963 0.344331 11.00000 0.17182 0.19837 = 0.10753 -0.12351 0.09600 -0.08914 AFIX 43 H1 2 1.019136 0.497326 0.392947 11.00000 -1.20000 AFIX 65 C2 1 1.195836 0.574195 0.386605 11.00000 0.07756 0.14379 = 0.15275 -0.05949 0.04234 -0.06110 AFIX 43 H2 2 1.213532 0.604534 0.463505 11.00000 -1.20000 AFIX 65 C00L 1 1.285859 0.593082 0.313943 11.00000 0.22611 0.08936 = 0.11471 0.03356 0.02251 0.06623 AFIX 43 H00L 2 1.363785 0.636058 0.342227 11.00000 -1.20000 AFIX 65 C00V 1 1.259412 0.547737 0.199006 11.00000 0.06296 0.12747 = 0.52370 -0.02473 0.13925 -0.06203 AFIX 43 H00V 2 1.319644 0.560374 0.150391 11.00000 -1.20000 AFIX 65 C00I 1 1.142943 0.483504 0.156731 11.00000 0.13518 0.15512 = 0.08144 -0.02239 -0.00312 -0.06110 AFIX 43 H00I 2 1.125248 0.453165 0.079831 11.00000 -1.20000 AFIX 0 O002 4 0.758129 0.508595 0.166476 11.00000 0.07867 0.13186 = 0.09579 -0.00314 0.03199 -0.01677 N2 3 0.064701 0.866719 0.410603 11.00000 0.02275 0.06499 = 0.20427 -0.01590 0.02708 0.01056 AFIX 93 H2A 2 0.108936 0.873931 0.484891 11.00000 -1.20000 H2B 2 -0.023770 0.868921 0.391020 11.00000 -1.20000 AFIX 0 O3 4 0.691750 0.098032 0.293027 11.00000 0.16384 0.07372 = 0.11136 -0.02654 0.06491 -0.03153 C3 1 0.650846 0.172702 0.232756 11.00000 0.15921 0.00242 = 0.51059 0.02491 0.14303 0.02324 O4 4 0.529617 0.224942 0.226227 11.00000 0.05061 0.58368 = 0.04082 -0.09361 0.03505 -0.07143 O004 4 0.814187 0.368361 0.337165 11.00000 0.06482 0.10097 = 0.04514 -0.00459 0.00328 -0.00780 N4 3 0.522369 0.975778 0.054755 11.00000 0.07651 0.06723 = 0.06034 0.04532 0.00217 -0.01209 C4 1 0.542288 0.914637 0.128490 11.00000 0.02147 0.11967 = 0.03385 0.02206 -0.00467 0.00764 O5 4 0.527060 0.720917 0.156367 11.00000 0.03512 0.09394 = 0.12295 -0.03134 0.01143 -0.01611 C8 1 0.368611 0.861048 0.461574 11.00000 0.04450 0.11334 = 0.10310 -0.01651 -0.04742 0.02464 AFIX 43 H8 2 0.358669 0.871246 0.539529 11.00000 -1.20000 AFIX 0 C9 1 0.489190 0.854775 0.424969 11.00000 0.01345 0.08455 = 0.18121 0.02642 0.04921 0.01633 AFIX 43 H9 2 0.576245 0.862471 0.476707 11.00000 -1.20000 AFIX 0 C10 1 0.146084 0.204508 0.431251 11.00000 0.06233 0.35147 = 0.42150 0.08057 0.05022 0.13076 AFIX 137 H10A 2 0.156255 0.281995 0.445243 11.00000 -1.50000 H10B 2 0.129827 0.169361 0.501512 11.00000 -1.50000 H10C 2 0.069658 0.191080 0.363391 11.00000 -1.50000 AFIX 0 C11 1 0.650072 0.561128 0.180835 11.00000 0.04731 0.03060 = 0.82215 -0.01201 0.03627 0.03777 AFIX 23 H11A 2 0.653704 0.563839 0.266310 11.00000 -1.20000 H11B 2 0.568470 0.520050 0.141451 11.00000 -1.20000 AFIX 0 C009 1 0.699044 0.207571 0.115066 11.00000 0.06677 0.12870 = 0.09224 0.01024 -0.02095 -0.05672 AFIX 13 H009 2 0.624591 0.191743 0.043584 11.00000 -1.20000 AFIX 0 C00A 1 0.752659 0.749207 0.199027 11.00000 0.05095 0.04080 = 0.10341 0.02054 0.00398 -0.01748 AFIX 13 H00A 2 0.832307 0.706626 0.242836 11.00000 -1.20000 AFIX 0 C00H 1 0.696598 0.809699 0.296079 11.00000 0.06068 0.11596 = 0.05143 0.03988 0.01002 0.01311 AFIX 13 H00H 2 0.698113 0.758108 0.362057 11.00000 -1.20000 AFIX 0 C00N 1 0.554286 0.820479 0.226039 11.00000 -0.00056 0.10594 = 0.07174 -0.05305 0.00309 -0.00686 C00O 1 0.637765 0.662323 0.137866 11.00000 0.02438 0.11571 = 0.04780 0.03430 -0.00534 0.01603 AFIX 13 H00O 2 0.631725 0.659702 0.051086 11.00000 -1.20000 AFIX 0 C00R 1 0.195231 0.106032 0.123786 11.00000 0.17833 0.07392 = 0.21080 -0.00297 0.08275 -0.05777 AFIX 137 H00D 2 0.145609 0.071688 0.175629 11.00000 -1.50000 H00E 2 0.269855 0.059544 0.116213 11.00000 -1.50000 H00F 2 0.134389 0.117740 0.045610 11.00000 -1.50000 AFIX 0 C00S 1 0.465047 0.834983 0.297723 11.00000 0.00472 0.14125 = 0.04571 0.02573 -0.01303 0.00984 O00T 4 0.793611 0.805407 0.120651 11.00000 0.03724 0.13740 = 0.08611 0.04682 -0.00722 -0.00661 AFIX 87 H00R 2 0.877961 0.804892 0.136674 11.00000 -1.50000 AFIX 0 C00U 1 0.276499 0.158810 0.405343 11.00000 0.24743 0.07219 = 0.31243 -0.05256 0.21747 -0.00567 AFIX 23 H00G 2 0.259257 0.083020 0.380556 11.00000 -1.20000 H00J 2 0.347576 0.158691 0.480359 11.00000 -1.20000 AFIX 0 C00W 1 0.333745 0.217225 0.310156 11.00000 0.18223 0.24058 = 0.31629 0.07238 -0.16611 0.10956 AFIX 13 H00W 2 0.354826 0.293359 0.335377 11.00000 -1.20000 AFIX 0 C00X 1 0.467020 0.157737 0.312296 11.00000 0.13234 0.11026 = 0.05660 -0.03647 0.00440 -0.02527 AFIX 23 H00K 2 0.449500 0.082892 0.284047 11.00000 -1.20000 H00M 2 0.527324 0.156927 0.392993 11.00000 -1.20000 AFIX 0 C00Y 1 0.829955 0.130073 0.112771 11.00000 0.09828 0.17627 = 0.17628 -0.01730 0.02519 0.05043 AFIX 137 H00N 2 0.837028 0.072668 0.171391 11.00000 -1.50000 H00P 2 0.912564 0.173236 0.131616 11.00000 -1.50000 H00Q 2 0.817681 0.098489 0.033949 11.00000 -1.50000 AFIX 0 P1 5 0.811014 0.396363 0.213722 11.00000 0.03766 0.08051 = 0.07891 0.03023 0.00468 0.00554 O1 4 0.952656 0.392144 0.174084 11.00000 0.03729 0.09103 = 0.06145 0.01882 0.02291 0.01657 N1 3 0.723005 0.310539 0.119467 11.00000 0.06085 0.06861 = 0.08202 0.06340 0.03343 0.01787 AFIX 43 H1A 2 0.680162 0.342512 0.053885 11.00000 -1.20000 AFIX 0 O2 4 0.771008 0.896377 0.342111 11.00000 0.07240 0.06313 = 0.25291 0.01633 0.07116 -0.02857 AFIX 87 H2C 2 0.773724 0.939586 0.287847 11.00000 -1.50000 AFIX 0 C010 1 0.252200 0.215912 0.177683 11.00000 0.19893 0.04583 = 0.60144 0.00096 0.29607 0.05084 AFIX 23 H01A 2 0.175515 0.266238 0.169192 11.00000 -1.20000 H01B 2 0.311271 0.244616 0.129424 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM Remdesivir form 4 in P2(1) REM wR2 = 0.4041, GooF = S = 1.033, Restrained GooF = 1.033 for all data REM R1 = 0.1592 for 1639 Fo > 4sig(Fo) and 0.2346 for all 3133 data REM 360 parameters refined using 8 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.171, deepest hole -0.198, 1-sigma level 0.050 Q1 1 0.7155 0.5770 0.0129 11.00000 0.05 0.17 Q2 1 0.1692 0.7114 0.1593 11.00000 0.05 0.16 Q3 1 0.1341 0.9608 0.2978 11.00000 0.05 0.15 Q4 1 0.2837 0.2570 0.5052 11.00000 0.05 0.14 Q5 1 0.7499 0.2355 0.0195 11.00000 0.05 0.14 Q6 1 0.1029 0.8115 0.3133 11.00000 0.05 0.14 Q7 1 0.8002 0.4358 0.2939 11.00000 0.05 0.14 Q8 1 0.7053 0.7207 0.3823 11.00000 0.05 0.14 Q9 1 0.7803 0.4128 0.1256 11.00000 0.05 0.13 Q10 1 0.3078 0.7401 0.4833 11.00000 0.05 0.13 Q11 1 0.4662 0.9588 0.3528 11.00000 0.05 0.13 Q12 1 0.1898 0.3771 0.1850 11.00000 0.05 0.13 Q13 1 0.4836 0.6802 0.1016 11.00000 0.05 0.13 Q14 1 0.8529 0.2407 0.3872 11.00000 0.05 0.13 Q15 1 0.8408 0.2540 0.3524 11.00000 0.05 0.13 Q16 1 0.8422 0.5149 0.3618 11.00000 0.05 0.12 Q17 1 0.6767 0.6766 0.3022 11.00000 0.05 0.12 Q18 1 0.4483 1.0107 0.0763 11.00000 0.05 0.12 Q19 1 0.8044 0.7371 0.3484 11.00000 0.05 0.12 Q20 1 0.7038 0.9424 0.2875 11.00000 0.05 0.12 ; _shelx_res_checksum 24604 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 N3 N 0.3408(8) 0.8374(12) 0.2722(13) 0.067(6) Uani 1 1 d G . . . . C00C C 0.2709(11) 0.8495(12) 0.3623(10) 0.078(8) Uani 1 1 d G . . . . C5 C 0.1280(11) 0.8533(11) 0.3324(11) 0.053(6) Uani 1 1 d G . . . . N00D N 0.0548(8) 0.8449(13) 0.2124(12) 0.071(6) Uani 1 1 d G . . . . C6 C 0.1246(10) 0.8328(15) 0.1223(10) 0.085(8) Uani 1 1 d G . . . . H6 H 0.075657 0.827289 0.042080 0.102 Uiso 1 1 calc R U . . . N5 N 0.2676(11) 0.8291(14) 0.1522(12) 0.090(9) Uani 1 1 d G . . . . C00F C 1.0529(16) 0.4646(16) 0.229(2) 0.112(14) Uani 1 1 d G . . . . C1 C 1.0794(19) 0.5100(19) 0.344(2) 0.148(18) Uani 1 1 d G . . . . H1 H 1.019136 0.497326 0.392947 0.178 Uiso 1 1 calc R U . . . C2 C 1.196(2) 0.5742(18) 0.387(2) 0.122(14) Uani 1 1 d G . . . . H2 H 1.213532 0.604534 0.463505 0.147 Uiso 1 1 calc R U . . . C00L C 1.2859(16) 0.5931(17) 0.314(2) 0.147(19) Uani 1 1 d G . . . . H00L H 1.363785 0.636058 0.342227 0.176 Uiso 1 1 calc R U . . . C00V C 1.2594(18) 0.548(2) 0.199(2) 0.23(3) Uani 1 1 d G . . . . H00V H 1.319644 0.560374 0.150391 0.272 Uiso 1 1 calc R U . . . C00I C 1.143(2) 0.4835(19) 0.1567(18) 0.129(13) Uani 1 1 d G . . . . H00I H 1.125248 0.453165 0.079831 0.155 Uiso 1 1 calc R U . . . O002 O 0.758(2) 0.509(2) 0.166(3) 0.100(9) Uani 1 1 d . . . . . N2 N 0.0647(17) 0.8667(15) 0.411(3) 0.098(11) Uani 1 1 d . . . . . H2A H 0.108936 0.873931 0.484891 0.117 Uiso 1 1 calc R U . . . H2B H -0.023770 0.868921 0.391020 0.117 Uiso 1 1 calc R U . . . O3 O 0.692(4) 0.098(2) 0.293(3) 0.111(11) Uani 1 1 d . . . . . C3 C 0.651(4) 0.1727(18) 0.233(7) 0.21(3) Uani 1 1 d . . . . . O4 O 0.530(2) 0.225(5) 0.226(3) 0.22(3) Uani 1 1 d . . . . . O004 O 0.8142(18) 0.368(2) 0.337(2) 0.072(6) Uani 1 1 d . . . . . N4 N 0.522(2) 0.9758(17) 0.055(3) 0.071(7) Uani 1 1 d . . . . . C4 C 0.5423(16) 0.915(2) 0.128(2) 0.060(7) Uani 1 1 d . . . . . O5 O 0.5271(17) 0.7209(18) 0.156(3) 0.085(9) Uani 1 1 d . . . . . C8 C 0.369(2) 0.861(2) 0.462(3) 0.099(10) Uani 1 1 d . . . . . H8 H 0.358669 0.871246 0.539529 0.118 Uiso 1 1 calc R U . . . C9 C 0.4892(18) 0.8548(18) 0.425(4) 0.089(11) Uani 1 1 d . . . . . H9 H 0.576245 0.862471 0.476707 0.106 Uiso 1 1 calc R U . . . C10 C 0.146(3) 0.205(5) 0.431(6) 0.28(4) Uani 1 1 d D . . . . H10A H 0.156255 0.281995 0.445243 0.420 Uiso 1 1 calc R U . . . H10B H 0.129827 0.169361 0.501512 0.420 Uiso 1 1 calc R U . . . H10C H 0.069658 0.191080 0.363391 0.420 Uiso 1 1 calc R U . . . C11 C 0.650(3) 0.561(2) 0.181(7) 0.31(5) Uani 1 1 d . . . . . H11A H 0.653704 0.563839 0.266310 0.375 Uiso 1 1 calc R U . . . H11B H 0.568470 0.520050 0.141451 0.375 Uiso 1 1 calc R U . . . C009 C 0.699(3) 0.208(3) 0.115(3) 0.103(11) Uani 1 1 d . . . . . H009 H 0.624591 0.191743 0.043584 0.124 Uiso 1 1 calc R U . . . C00A C 0.753(2) 0.7492(16) 0.199(3) 0.068(8) Uani 1 1 d . . . . . H00A H 0.832307 0.706626 0.242836 0.081 Uiso 1 1 calc R U . . . C00H C 0.697(2) 0.810(2) 0.296(2) 0.077(8) Uani 1 1 d . . . . . H00H H 0.698113 0.758108 0.362057 0.092 Uiso 1 1 calc R U . . . C00N C 0.5543(13) 0.8205(19) 0.226(2) 0.060(7) Uani 1 1 d . . . . . C00O C 0.6378(16) 0.662(2) 0.138(3) 0.065(7) Uani 1 1 d . . . . . H00O H 0.631725 0.659702 0.051086 0.078 Uiso 1 1 calc R U . . . C00R C 0.195(4) 0.106(2) 0.124(4) 0.148(18) Uani 1 1 d D . . . . H00D H 0.145609 0.071688 0.175629 0.222 Uiso 1 1 calc R U . . . H00E H 0.269855 0.059544 0.116213 0.222 Uiso 1 1 calc R U . . . H00F H 0.134389 0.117740 0.045610 0.222 Uiso 1 1 calc R U . . . C00S C 0.4650(17) 0.835(2) 0.298(2) 0.067(7) Uani 1 1 d . . . . . O00T O 0.7936(18) 0.805(2) 0.121(2) 0.091(8) Uani 1 1 d . . . . . H00R H 0.877961 0.804892 0.136674 0.136 Uiso 1 1 calc R U . . . C00U C 0.276(4) 0.159(2) 0.405(5) 0.18(3) Uani 1 1 d D . . . . H00G H 0.259257 0.083020 0.380556 0.221 Uiso 1 1 calc R U . . . H00J H 0.347576 0.158691 0.480359 0.221 Uiso 1 1 calc R U . . . C00W C 0.334(3) 0.217(3) 0.310(3) 0.29(5) Uani 1 1 d D . . . . H00W H 0.354826 0.293359 0.335377 0.344 Uiso 1 1 calc R U . . . C00X C 0.467(3) 0.158(2) 0.312(3) 0.103(11) Uani 1 1 d D . . . . H00K H 0.449500 0.082892 0.284047 0.124 Uiso 1 1 calc R U . . . H00M H 0.527324 0.156927 0.392993 0.124 Uiso 1 1 calc R U . . . C00Y C 0.830(4) 0.130(4) 0.113(5) 0.152(17) Uani 1 1 d . . . . . H00N H 0.837028 0.072668 0.171391 0.228 Uiso 1 1 calc R U . . . H00P H 0.912564 0.173236 0.131616 0.228 Uiso 1 1 calc R U . . . H00Q H 0.817681 0.098489 0.033949 0.228 Uiso 1 1 calc R U . . . P1 P 0.8110(10) 0.3964(10) 0.2137(14) 0.067(4) Uani 1 1 d . . . . . O1 O 0.9527(15) 0.3921(16) 0.174(2) 0.061(5) Uani 1 1 d . . . . . N1 N 0.7230(19) 0.3105(16) 0.119(2) 0.068(7) Uani 1 1 d . . . . . H1A H 0.680162 0.342512 0.053885 0.081 Uiso 1 1 calc R U . . . O2 O 0.771(2) 0.8964(18) 0.342(4) 0.124(14) Uani 1 1 d . . . . . H2C H 0.773724 0.939586 0.287847 0.186 Uiso 1 1 calc R U . . . C010 C 0.252(3) 0.2159(18) 0.178(4) 0.25(4) Uani 1 1 d D . . . . H01A H 0.175515 0.266238 0.169192 0.297 Uiso 1 1 calc R U . . . H01B H 0.311271 0.244616 0.129424 0.297 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 N3 0.086(18) 0.075(13) 0.021(11) -0.004(11) -0.022(11) 0.016(11) C00C 0.087(18) 0.068(15) 0.08(2) 0.020(14) 0.018(17) 0.016(12) C5 0.023(9) 0.048(11) 0.10(2) -0.021(11) 0.036(12) 0.015(7) N00D 0.045(9) 0.097(15) 0.055(15) 0.003(13) -0.016(10) -0.008(9) C6 0.096(16) 0.16(2) 0.005(11) -0.010(16) 0.018(12) 0.016(18) N5 0.029(9) 0.110(17) 0.15(3) 0.024(17) 0.067(14) 0.006(10) C00F 0.050(15) 0.12(2) 0.16(4) 0.08(2) 0.013(19) -0.020(14) C1 0.17(3) 0.20(4) 0.11(3) -0.12(3) 0.10(3) -0.09(3) C2 0.078(17) 0.14(3) 0.15(4) -0.06(3) 0.04(2) -0.061(19) C00L 0.23(5) 0.09(2) 0.11(4) 0.03(2) 0.02(4) 0.07(3) C00V 0.063(18) 0.13(3) 0.52(11) -0.02(4) 0.14(4) -0.06(2) C00I 0.14(3) 0.16(3) 0.08(3) -0.02(2) 0.00(2) -0.06(2) O002 0.079(14) 0.13(2) 0.10(3) -0.003(18) 0.032(17) -0.017(15) N2 0.023(8) 0.065(12) 0.20(3) -0.016(16) 0.027(14) 0.011(7) O3 0.16(3) 0.074(18) 0.11(3) -0.027(16) 0.06(2) -0.032(16) C3 0.16(3) 0.002(10) 0.51(10) 0.02(3) 0.14(5) 0.023(14) O4 0.051(11) 0.58(9) 0.041(15) -0.09(4) 0.035(12) -0.07(3) O004 0.065(10) 0.101(14) 0.045(14) -0.005(13) 0.003(10) -0.008(10) N4 0.077(14) 0.067(13) 0.060(19) 0.045(13) 0.002(13) -0.012(10) C4 0.021(9) 0.12(2) 0.034(16) 0.022(17) -0.005(10) 0.008(10) O5 0.035(9) 0.094(15) 0.12(3) -0.031(15) 0.011(13) -0.016(9) C8 0.044(12) 0.11(2) 0.10(2) -0.02(2) -0.047(15) 0.025(12) C9 0.013(8) 0.085(15) 0.18(4) 0.026(19) 0.049(15) 0.016(8) C10 0.06(2) 0.35(8) 0.42(11) 0.08(7) 0.05(4) 0.13(4) C11 0.047(16) 0.031(12) 0.82(15) -0.01(3) 0.04(4) 0.038(11) C009 0.067(15) 0.13(3) 0.09(3) 0.01(2) -0.021(17) -0.057(16) C00A 0.051(12) 0.041(10) 0.10(2) 0.021(14) 0.004(14) -0.017(9) C00H 0.061(14) 0.12(2) 0.051(18) 0.040(17) 0.010(13) 0.013(15) C00N -0.001(7) 0.106(16) 0.072(18) -0.053(15) 0.003(9) -0.007(8) C00O 0.024(10) 0.116(19) 0.048(18) 0.034(15) -0.005(10) 0.016(11) C00R 0.18(3) 0.074(19) 0.21(5) 0.00(2) 0.08(4) -0.06(2) C00S 0.005(9) 0.14(2) 0.046(15) 0.026(17) -0.013(10) 0.010(10) O00T 0.037(9) 0.137(19) 0.086(18) 0.047(17) -0.007(11) -0.007(11) C00U 0.25(5) 0.072(19) 0.31(8) -0.05(3) 0.22(6) -0.01(3) C00W 0.18(5) 0.24(7) 0.32(10) 0.07(6) -0.17(6) 0.11(5) C00X 0.13(3) 0.11(2) 0.06(2) -0.036(18) 0.00(2) -0.03(2) C00Y 0.10(2) 0.18(4) 0.18(5) -0.02(3) 0.03(3) 0.05(2) P1 0.038(5) 0.081(8) 0.079(12) 0.030(8) 0.005(7) 0.006(6) O1 0.037(7) 0.091(12) 0.061(14) 0.019(11) 0.023(9) 0.017(9) N1 0.061(11) 0.069(13) 0.082(19) 0.063(13) 0.033(13) 0.018(10) O2 0.072(12) 0.063(12) 0.25(4) 0.016(18) 0.07(2) -0.029(11) C010 0.20(4) 0.046(15) 0.60(13) 0.00(3) 0.30(7) 0.051(19) 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' P P 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 C00S N3 C00C 120.2(17) . . ? C00S N3 N5 119.8(16) . . ? C00C N3 N5 120.0 . . ? C00S N3 C9 45.1(14) . . ? C00C N3 C9 75.2(13) . . ? N5 N3 C9 164.5(9) . . ? C8 C00C C5 135.5(18) . . ? C8 C00C N3 104.4(19) . . ? C5 C00C N3 120.0 . . ? N2 C5 C00C 120.8(16) . . ? N2 C5 N00D 119.1(17) . . ? C00C C5 N00D 120.0 . . ? C6 N00D C5 120.0 . . ? N00D C6 N5 120.0 . . ? C6 N5 N3 120.0 . . ? O1 C00F C1 129.8(15) . . ? O1 C00F C00I 110.0(17) . . ? C1 C00F C00I 120.0 . . ? O1 C00F P1 34.3(10) . . ? C1 C00F P1 98.8(12) . . ? C00I C00F P1 140.0(11) . . ? C00F C1 C2 120.0 . . ? C00F C1 P1 54.6(9) . . ? C2 C1 P1 169.9(9) . . ? C00L C2 C1 120.0 . . ? C2 C00L C00V 120.0 . . ? C00L C00V C00I 120.0 . . ? C00V C00I C00F 120.0 . . ? C11 O002 P1 129(3) . . ? O3 C3 O4 126(5) . . ? O3 C3 C009 125(3) . . ? O4 C3 C009 106(4) . . ? C3 O4 C00X 103(5) . . ? N4 C4 C00N 173(2) . . ? C00O O5 C00N 118.2(17) . . ? C00C C8 C9 105(3) . . ? C8 C9 C00S 112(3) . . ? C8 C9 N3 76(2) . . ? C00S C9 N3 36.6(13) . . ? O002 C11 C00O 115(4) . . ? O002 C11 P1 27.7(17) . . ? C00O C11 P1 142(3) . . ? N1 C009 C3 109(3) . . ? N1 C009 C00Y 115(3) . . ? C3 C009 C00Y 106(3) . . ? N1 C009 P1 23.8(15) . . ? C3 C009 P1 93(2) . . ? C00Y C009 P1 105(2) . . ? O00T C00A C00H 119(2) . . ? O00T C00A C00O 112(3) . . ? C00H C00A C00O 106.2(19) . . ? O2 C00H C00N 122(2) . . ? O2 C00H C00A 113(2) . . ? C00N C00H C00A 97(2) . . ? C00S C00N O5 112(2) . . ? C00S C00N C00H 112(2) . . ? O5 C00N C00H 104.7(19) . . ? C00S C00N C4 112(2) . . ? O5 C00N C4 105(2) . . ? C00H C00N C4 110.2(17) . . ? C11 C00O O5 116(3) . . ? C11 C00O C00A 118(3) . . ? O5 C00O C00A 96(2) . . ? N3 C00S C00N 130(2) . . ? N3 C00S C9 98(2) . . ? C00N C00S C9 131.2(19) . . ? C10 C00U C00W 118(3) . . ? C00X C00W C00U 105(3) . . ? C00X C00W C010 105(3) . . ? C00U C00W C010 120(4) . . ? C00W C00X O4 104(3) . . ? O004 P1 O002 118.8(16) . . ? O004 P1 O1 117.7(14) . . ? O002 P1 O1 100.7(13) . . ? O004 P1 N1 112.2(16) . . ? O002 P1 N1 105.3(19) . . ? O1 P1 N1 99.7(14) . . ? O004 P1 C00F 102.7(13) . . ? O002 P1 C00F 88.4(13) . . ? O1 P1 C00F 28.9(10) . . ? N1 P1 C00F 128.4(12) . . ? O004 P1 C11 101(2) . . ? O002 P1 C11 23.5(15) . . ? O1 P1 C11 124.0(15) . . ? N1 P1 C11 101.1(17) . . ? C00F P1 C11 108.2(13) . . ? O004 P1 C009 96.5(15) . . ? O002 P1 C009 123.4(18) . . ? O1 P1 C009 99.3(13) . . ? N1 P1 C009 18.8(10) . . ? C00F P1 C009 127.3(11) . . ? C11 P1 C009 115.6(15) . . ? O004 P1 C1 80.0(13) . . ? O002 P1 C1 87.3(15) . . ? O1 P1 C1 54.4(11) . . ? N1 P1 C1 153.4(9) . . ? C00F P1 C1 26.6(5) . . ? C11 P1 C1 99.4(14) . . ? C009 P1 C1 144.8(9) . . ? C00F O1 P1 116.8(18) . . ? C009 N1 P1 137(2) . . ? C00R C010 C00W 118(3) . . ? 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 N3 C00S 1.21(2) . ? N3 C00C 1.3900 . ? N3 N5 1.3900 . ? N3 C9 2.01(4) . ? C00C C8 1.31(3) . ? C00C C5 1.3900 . ? C5 N2 1.23(3) . ? C5 N00D 1.3900 . ? N00D C6 1.3900 . ? C6 N5 1.3900 . ? C00F O1 1.37(3) . ? C00F C1 1.3900 . ? C00F C00I 1.3900 . ? C00F P1 2.53(2) . ? C1 C2 1.3900 . ? C1 P1 3.07(3) . ? C2 C00L 1.3900 . ? C00L C00V 1.3900 . ? C00V C00I 1.3900 . ? O002 C11 1.30(4) . ? O002 P1 1.52(4) . ? O3 C3 1.15(6) . ? C3 O4 1.36(5) . ? C3 C009 1.60(7) . ? O4 C00X 1.53(6) . ? O004 P1 1.45(3) . ? N4 C4 1.11(3) . ? C4 C00N 1.59(4) . ? O5 C00O 1.38(3) . ? O5 C00N 1.44(4) . ? C8 C9 1.38(4) . ? C9 C00S 1.44(4) . ? C10 C00U 1.52(3) . ? C11 C00O 1.32(5) . ? C11 P1 2.55(4) . ? C009 N1 1.28(4) . ? C009 C00Y 1.62(5) . ? C009 P1 2.69(5) . ? C00A O00T 1.28(3) . ? C00A C00H 1.55(4) . ? C00A C00O 1.59(4) . ? C00H O2 1.33(4) . ? C00H C00N 1.46(3) . ? C00N C00S 1.37(3) . ? C00R C010 1.53(3) . ? C00U C00W 1.53(3) . ? C00W C00X 1.52(3) . ? C00W C010 1.53(4) . ? P1 O1 1.60(2) . ? P1 N1 1.60(3) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2B O2 0.86 2.02 2.88(4) 172.2 1_455 yes N2 H2A O004 0.86 1.99 2.84(6) 168.7 2_656 yes O00T H00R N00D 0.82 1.84 2.61(4) 157.7 1_655 yes O2 H2C O3 0.82 2.11 2.60(6) 118.8 1_565 yes 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 C00S N3 C00C C8 3(2) . . . . ? N5 N3 C00C C8 -176.5(17) . . . . ? C9 N3 C00C C8 0.2(15) . . . . ? C00S N3 C00C C5 179.4(19) . . . . ? N5 N3 C00C C5 0.0 . . . . ? C9 N3 C00C C5 176.6(11) . . . . ? C8 C00C C5 N2 -3(3) . . . . ? N3 C00C C5 N2 -178.1(15) . . . . ? C8 C00C C5 N00D 175(2) . . . . ? N3 C00C C5 N00D 0.0 . . . . ? N2 C5 N00D C6 178.2(15) . . . . ? C00C C5 N00D C6 0.0 . . . . ? C5 N00D C6 N5 0.0 . . . . ? N00D C6 N5 N3 0.0 . . . . ? C00S N3 N5 C6 -179.4(19) . . . . ? C00C N3 N5 C6 0.0 . . . . ? C9 N3 N5 C6 -168(4) . . . . ? O1 C00F C1 C2 174(2) . . . . ? C00I C00F C1 C2 0.0 . . . . ? P1 C00F C1 C2 -169.9(12) . . . . ? O1 C00F C1 P1 -16.4(14) . . . . ? C00I C00F C1 P1 169.9(12) . . . . ? C00F C1 C2 C00L 0.0 . . . . ? P1 C1 C2 C00L -55(5) . . . . ? C1 C2 C00L C00V 0.0 . . . . ? C2 C00L C00V C00I 0.0 . . . . ? C00L C00V C00I C00F 0.0 . . . . ? O1 C00F C00I C00V -174.8(18) . . . . ? C1 C00F C00I C00V 0.0 . . . . ? P1 C00F C00I C00V 164.3(19) . . . . ? O3 C3 O4 C00X -2(7) . . . . ? C009 C3 O4 C00X 160(3) . . . . ? C5 C00C C8 C9 -175.9(14) . . . . ? N3 C00C C8 C9 0(2) . . . . ? C00C C8 C9 C00S -2(3) . . . . ? C00C C8 C9 N3 0.2(15) . . . . ? P1 O002 C11 C00O 174(3) . . . . ? O3 C3 C009 N1 -133(5) . . . . ? O4 C3 C009 N1 64(4) . . . . ? O3 C3 C009 C00Y -9(6) . . . . ? O4 C3 C009 C00Y -171(3) . . . . ? O3 C3 C009 P1 -115(5) . . . . ? O4 C3 C009 P1 83(3) . . . . ? O00T C00A C00H O2 -43(3) . . . . ? C00O C00A C00H O2 -170(2) . . . . ? O00T C00A C00H C00N 86(2) . . . . ? C00O C00A C00H C00N -41(2) . . . . ? C00O O5 C00N C00S -143(3) . . . . ? C00O O5 C00N C00H -21(3) . . . . ? C00O O5 C00N C4 95(3) . . . . ? O2 C00H C00N C00S -79(3) . . . . ? C00A C00H C00N C00S 158(2) . . . . ? O2 C00H C00N O5 159(3) . . . . ? C00A C00H C00N O5 36(2) . . . . ? O2 C00H C00N C4 47(3) . . . . ? C00A C00H C00N C4 -76(2) . . . . ? O002 C11 C00O O5 -178(4) . . . . ? P1 C11 C00O O5 -173(5) . . . . ? O002 C11 C00O C00A -65(7) . . . . ? P1 C11 C00O C00A -60(8) . . . . ? C00N O5 C00O C11 119(4) . . . . ? C00N O5 C00O C00A -6(3) . . . . ? O00T C00A C00O C11 134(4) . . . . ? C00H C00A C00O C11 -94(4) . . . . ? O00T C00A C00O O5 -103(3) . . . . ? C00H C00A C00O O5 29(3) . . . . ? C00C N3 C00S C00N 178(2) . . . . ? N5 N3 C00S C00N -3(4) . . . . ? C9 N3 C00S C00N -179(4) . . . . ? C00C N3 C00S C9 -4(2) . . . . ? N5 N3 C00S C9 175.6(13) . . . . ? O5 C00N C00S N3 -55(4) . . . . ? C00H C00N C00S N3 -173(3) . . . . ? C4 C00N C00S N3 62(4) . . . . ? O5 C00N C00S C9 127(3) . . . . ? C00H C00N C00S C9 9(4) . . . . ? C4 C00N C00S C9 -116(3) . . . . ? C8 C9 C00S N3 3(3) . . . . ? C8 C9 C00S C00N -178(3) . . . . ? N3 C9 C00S C00N 179(4) . . . . ? C10 C00U C00W C00X 176(4) . . . . ? C10 C00U C00W C010 -66(6) . . . . ? C00U C00W C00X O4 -174(3) . . . . ? C010 C00W C00X O4 59(3) . . . . ? C3 O4 C00X C00W 178(4) . . . . ? C11 O002 P1 O004 -44(5) . . . . ? C11 O002 P1 O1 -174(4) . . . . ? C11 O002 P1 N1 83(5) . . . . ? C11 O002 P1 C00F -148(5) . . . . ? C11 O002 P1 C009 77(5) . . . . ? C11 O002 P1 C1 -121(5) . . . . ? C1 C00F O1 P1 30(3) . . . . ? C00I C00F O1 P1 -156.1(14) . . . . ? O004 P1 O1 C00F -64(2) . . . . ? O002 P1 O1 C00F 67(2) . . . . ? N1 P1 O1 C00F 174.3(17) . . . . ? C11 P1 O1 C00F 64(3) . . . . ? C009 P1 O1 C00F -166.7(17) . . . . ? C1 P1 O1 C00F -12.3(11) . . . . ? C3 C009 N1 P1 52(4) . . . . ? C00Y C009 N1 P1 -67(5) . . . . ? O004 P1 N1 C009 -35(3) . . . . ? O002 P1 N1 C009 -166(3) . . . . ? O1 P1 N1 C009 90(3) . . . . ? C00F P1 N1 C009 94(3) . . . . ? C11 P1 N1 C009 -142(3) . . . . ? C1 P1 N1 C009 78(4) . . . . ? C00X C00W C010 C00R 70(4) . . . . ? C00U C00W C010 C00R -47(4) . . . . ?