#------------------------------------------------------------------------------ #$Date: 2021-05-13 07:03:54 +0300 (Thu, 13 May 2021) $ #$Revision: 265167 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/28/7242822.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_7242822 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 H34 N6 O8 P' _chemical_formula_weight 601.55 _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 100.9(6) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.21(4) _cell_length_b 12.49(14) _cell_length_c 10.85(10) _cell_measurement_temperature 80(2) _cell_volume 1359(2) _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 0.950 _diffrn_measured_fraction_theta_max 0.950 _diffrn_radiation_wavelength 0.02508 _diffrn_reflns_av_R_equivalents 0.2297 _diffrn_reflns_av_unetI/netI 0.2468 _diffrn_reflns_Laue_measured_fraction_full 0.950 _diffrn_reflns_Laue_measured_fraction_max 0.950 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 11574 _diffrn_reflns_point_group_measured_fraction_full 0.915 _diffrn_reflns_point_group_measured_fraction_max 0.915 _diffrn_reflns_theta_full 0.798 _diffrn_reflns_theta_max 0.798 _diffrn_reflns_theta_min 0.089 _exptl_absorpt_coefficient_mu 0.000 _exptl_crystal_density_diffrn 1.470 _exptl_crystal_F_000 234 _refine_diff_density_max 0.242 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.070 _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 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 360 _refine_ls_number_reflns 3562 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.2331 _refine_ls_R_factor_gt 0.1609 _refine_ls_shift/su_max 0.969 _refine_ls_shift/su_mean 0.018 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2667P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3680 _refine_ls_wR_factor_ref 0.4225 _reflns_Friedel_coverage 0.828 _reflns_Friedel_fraction_full 0.876 _reflns_Friedel_fraction_max 0.876 _reflns_number_gt 2006 _reflns_number_total 3562 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra03100g2.cif _cod_data_source_block temp_a_init _cod_original_cell_volume 1359(21) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7242822 _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 II in P2(1) temp_a_init.res created by SHELXL-2018/3 at 18:27:24 on 14-Oct-2020 REM Old TITL Remdesivir Form II in P2(1) REM SHELXT solution in P2(1): R1 0.290, Rweak 0.183, Alpha 0.085 REM 0.000 for 0 systematic absences, Orientation as input REM Flack x = -1.929 ( 0.542 ) from 757 Parsons' quotients REM Formula found by SHELXT: C30 N5 O6 P CELL 0.02508 10.2100 12.4900 10.8500 90.000 100.850 90.000 ZERR 2.000 0.0400 0.1400 0.1000 0.000 0.550 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 68 12 16 2 EQIV $1 x, y+1, z EQIV $2 x+1, y, z EQIV $3 -x+1, y+1/2, -z+1 HTAB O1 O4_$1 HTAB N1 O1_$2 HTAB N1 O00X_$3 ACTA CONF L.S. 10 BOND LIST 6 FMAP 2 PLAN 20 TEMP -193 WGHT 0.266700 FVAR 1.82157 AFIX 66 N2 3 0.672265 0.800951 0.725016 11.00000 0.05381 0.06581 = 0.07447 0.04060 0.01482 0.00570 N3 3 0.738952 0.784692 0.847569 11.00000 0.02060 0.09554 = 0.09301 -0.00045 0.01326 -0.00659 C00K 1 0.877537 0.784634 0.874928 11.00000 0.04863 0.08386 = 0.09396 0.04444 -0.01589 0.00081 AFIX 43 H00K 2 0.923114 0.773521 0.958688 11.00000 -1.20000 AFIX 65 N00B 3 0.949436 0.800836 0.779734 11.00000 0.06402 0.06220 = 0.07800 0.04629 0.01957 0.03084 C004 1 0.882751 0.817096 0.657180 11.00000 0.02785 0.08596 = 0.12432 0.02870 0.03762 -0.00543 C00H 1 0.744166 0.817154 0.629820 11.00000 0.01968 0.10470 = 0.07289 0.01884 -0.00809 0.01053 AFIX 66 C3 1 -0.080244 0.443104 0.794805 11.00000 0.04373 0.08494 = 0.12854 0.07694 0.03333 0.00934 C00V 1 -0.102251 0.487896 0.675409 11.00000 0.07267 0.08647 = 0.09758 -0.02006 0.02962 -0.00856 AFIX 43 H00V 2 -0.032894 0.488290 0.628050 11.00000 -1.20000 AFIX 65 C00Q 1 -0.225737 0.532112 0.625305 11.00000 0.09479 0.07914 = 0.11237 -0.00082 0.02294 0.02005 AFIX 43 H00Q 2 -0.240777 0.562725 0.543703 11.00000 -1.20000 AFIX 65 C00R 1 -0.327218 0.531536 0.694597 11.00000 0.09025 0.08339 = 0.18611 -0.03851 0.03723 0.03773 AFIX 43 H00R 2 -0.411615 0.561756 0.660352 11.00000 -1.20000 AFIX 65 C015 1 -0.305213 0.486744 0.813993 11.00000 0.05941 0.10882 = 0.13456 0.00072 0.05039 0.03586 AFIX 43 H015 2 -0.374571 0.486351 0.861351 11.00000 -1.20000 AFIX 65 C00W 1 -0.181727 0.442528 0.864099 11.00000 0.02993 0.17197 = 0.15135 -0.09394 0.01989 -0.00596 AFIX 43 H00W 2 -0.166688 0.411915 0.945701 11.00000 -1.20000 AFIX 0 P001 5 0.156446 0.392042 0.794685 11.00000 0.03312 0.07849 = 0.05551 -0.02806 0.00805 -0.00075 O1 4 0.262107 0.877086 0.663819 11.00000 0.04468 0.12112 = 0.09509 0.02517 -0.00941 -0.00646 AFIX 147 H1C 2 0.247870 0.910733 0.727027 11.00000 -1.50000 AFIX 0 N1 3 0.950549 0.826006 0.572167 11.00000 0.05153 0.10992 = 0.09455 -0.01604 0.02267 -0.02481 AFIX 93 H1A 2 0.910311 0.832461 0.493345 11.00000 -1.20000 H1B 2 1.038209 0.825783 0.591524 11.00000 -1.20000 AFIX 0 C1 1 0.530233 0.822817 0.567061 11.00000 0.03012 0.11332 = 0.08186 0.02998 -0.01733 0.00626 AFIX 43 H1 2 0.444933 0.831559 0.515205 11.00000 -1.20000 AFIX 0 O2 4 0.026123 0.399209 0.850489 11.00000 0.03114 0.08915 = 0.14331 0.00973 0.03960 -0.00380 O002 4 0.214443 0.498847 0.840277 11.00000 0.07251 0.08028 = 0.06927 -0.01914 -0.00891 0.02723 C2 1 0.459092 0.780776 0.761516 11.00000 0.02870 0.06509 = 0.09901 0.03086 -0.00874 0.01323 O3 4 0.052769 0.160004 0.867289 11.00000 0.12973 0.07621 = 0.10980 0.00101 0.04949 -0.01680 O4 4 0.164341 0.039424 0.762461 11.00000 0.06661 0.18355 = 0.61589 -0.14910 0.09416 -0.01560 C003 1 0.475975 0.854753 0.867162 11.00000 0.04125 0.03292 = 0.06526 -0.01207 0.00851 -0.00466 N4 3 0.245295 0.301130 0.879305 11.00000 0.09778 0.05772 = 0.04593 -0.02985 0.01762 -0.01907 AFIX 43 H4 2 0.283411 0.316750 0.956866 11.00000 -1.20000 AFIX 0 C4 1 0.389582 0.151173 0.905017 11.00000 0.06209 0.08922 = 0.15220 0.01595 0.00009 0.04181 AFIX 137 H4A 2 0.391198 0.073424 0.893243 11.00000 -1.50000 H4B 2 0.394529 0.167301 0.994169 11.00000 -1.50000 H4C 2 0.465945 0.183542 0.876246 11.00000 -1.50000 AFIX 0 O5 4 0.465629 0.682936 0.815698 11.00000 0.03499 0.07543 = 0.07843 0.01664 0.01912 0.00437 O006 4 0.202032 0.786179 0.865577 11.00000 0.05279 0.16571 = 0.09066 0.04710 0.01528 0.07133 AFIX 147 H00I 2 0.121263 0.800283 0.838695 11.00000 -1.50000 AFIX 0 C00C 1 0.552740 0.799478 0.684036 11.00000 0.02888 0.06603 = 0.05667 0.01213 0.01830 -0.01213 C00D 1 0.263591 0.195617 0.831167 11.00000 0.03440 0.09103 = 0.15187 0.00827 0.03720 0.00769 AFIX 13 H00D 2 0.276226 0.203980 0.742491 11.00000 -1.20000 AFIX 0 N00F 3 0.494874 0.915157 0.944993 11.00000 0.04859 0.09108 = 0.06820 -0.01608 0.00752 -0.01150 C00G 1 0.244148 0.717969 0.789323 11.00000 0.01376 0.10385 = 0.17330 0.03852 0.04017 0.00659 AFIX 13 H00G 2 0.166361 0.678109 0.740601 11.00000 -1.20000 AFIX 0 C00L 1 0.310558 0.788325 0.696745 11.00000 0.05895 0.05782 = 0.06229 0.03564 -0.02552 -0.00048 AFIX 13 H00L 2 0.302634 0.745361 0.617916 11.00000 -1.20000 AFIX 0 C00N 1 0.343829 0.642449 0.849200 11.00000 0.04337 0.06627 = 0.09303 -0.02917 -0.00336 0.01705 AFIX 13 H00N 2 0.349989 0.642205 0.942280 11.00000 -1.20000 AFIX 0 C00P 1 0.655673 0.833434 0.528041 11.00000 0.05801 0.08791 = 0.08175 0.01676 0.01301 -0.02485 AFIX 43 H00P 2 0.671168 0.848893 0.446260 11.00000 -1.20000 AFIX 0 C00T 1 -0.290039 0.074086 0.751698 11.00000 0.05147 0.22829 = 0.13829 0.07578 0.01702 -0.00981 AFIX 23 H00A 2 -0.294193 0.047036 0.836643 11.00000 -1.20000 H00B 2 -0.278322 0.011967 0.698143 11.00000 -1.20000 AFIX 0 C00U 1 0.324848 0.537477 0.799408 11.00000 0.04588 0.08332 = 0.08122 0.00310 0.02919 -0.00365 AFIX 23 H00C 2 0.309531 0.539069 0.706574 11.00000 -1.20000 H00E 2 0.403749 0.492250 0.830635 11.00000 -1.20000 AFIX 0 O00X 4 0.147864 0.367586 0.671247 11.00000 0.03161 0.11192 = 0.14536 -0.07306 0.03098 -0.01639 C00Y 1 0.149774 0.127394 0.829760 11.00000 0.08223 0.15185 = 0.09450 -0.01467 0.01378 0.06176 C00Z 1 -0.139472 0.185118 0.659636 11.00000 0.08040 0.08514 = 0.12981 0.00472 0.01831 -0.03329 AFIX 23 H00F 2 -0.051501 0.220248 0.684168 11.00000 -1.20000 H00H 2 -0.204466 0.240093 0.621432 11.00000 -1.20000 AFIX 0 C010 1 -0.176104 0.146554 0.758978 11.00000 0.07089 0.05667 = 0.10885 0.00901 -0.00060 -0.00306 AFIX 13 H010 2 -0.198777 0.210425 0.806436 11.00000 -1.20000 AFIX 0 C011 1 -0.129568 0.092476 0.556723 11.00000 0.07271 0.08766 = 0.15150 0.02078 0.03384 0.00675 AFIX 137 H01A 2 -0.090235 0.122509 0.488581 11.00000 -1.50000 H01B 2 -0.219035 0.065178 0.522599 11.00000 -1.50000 H01C 2 -0.073460 0.033848 0.596899 11.00000 -1.50000 AFIX 0 C012 1 -0.061981 0.088313 0.850345 11.00000 0.21352 0.08496 = 0.07231 -0.03370 -0.02409 -0.08020 AFIX 23 H01D 2 -0.089044 0.074132 0.931768 11.00000 -1.20000 H01E 2 -0.040248 0.019293 0.814078 11.00000 -1.20000 AFIX 0 C013 1 -0.433449 0.137373 0.691725 11.00000 0.26028 0.22556 = 0.22414 0.02143 -0.01771 -0.17633 AFIX 137 H01F 2 -0.418083 0.187454 0.626381 11.00000 -1.50000 H01G 2 -0.464964 0.176882 0.758540 11.00000 -1.50000 H01H 2 -0.500791 0.084629 0.655339 11.00000 -1.50000 AFIX 0 HKLF 4 REM Remdesivir Form II in P2(1) REM wR2 = 0.4225, GooF = S = 1.042, Restrained GooF = 1.042 for all data REM R1 = 0.1609 for 2006 Fo > 4sig(Fo) and 0.2331 for all 3562 data REM 360 parameters refined using 1 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.242, deepest hole -0.226, 1-sigma level 0.070 Q1 1 -0.1859 -0.0290 0.9237 11.00000 0.05 0.24 Q2 1 -0.3782 0.2946 0.8180 11.00000 0.05 0.21 Q3 1 0.2837 0.1802 0.6645 11.00000 0.05 0.20 Q4 1 -0.1435 -0.0086 0.7249 11.00000 0.05 0.19 Q5 1 0.5698 0.2863 0.8761 11.00000 0.05 0.19 Q6 1 -0.6148 0.1668 0.5563 11.00000 0.05 0.19 Q7 1 0.3478 0.1704 0.9951 11.00000 0.05 0.19 Q8 1 -0.0690 -0.0584 0.6360 11.00000 0.05 0.19 Q9 1 -0.4391 0.2906 0.6601 11.00000 0.05 0.19 Q10 1 0.3248 0.1407 1.1284 11.00000 0.05 0.18 Q11 1 0.9722 0.9084 0.4467 11.00000 0.05 0.18 Q12 1 -0.3125 0.3244 0.9336 11.00000 0.05 0.17 Q13 1 -0.3354 0.6365 0.7976 11.00000 0.05 0.17 Q14 1 0.3184 0.4942 0.6746 11.00000 0.05 0.17 Q15 1 0.4268 0.8040 0.4209 11.00000 0.05 0.17 Q16 1 -0.0191 -0.0057 0.5067 11.00000 0.05 0.17 Q17 1 -0.2457 0.3172 0.8042 11.00000 0.05 0.16 Q18 1 0.2638 0.6151 0.6216 11.00000 0.05 0.16 Q19 1 0.8202 0.6222 0.9352 11.00000 0.05 0.15 Q20 1 0.8817 0.7060 0.9346 11.00000 0.05 0.15 ; _shelx_res_checksum 49141 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 N2 N 0.6723(6) 0.8010(12) 0.7250(10) 0.064(5) Uani 1 1 d G . . . . N3 N 0.7390(8) 0.7847(13) 0.8476(9) 0.069(5) Uani 1 1 d G . . . . C00K C 0.8775(9) 0.7846(15) 0.8749(9) 0.079(7) Uani 1 1 d G . . . . H00K H 0.923114 0.773521 0.958688 0.095 Uiso 1 1 calc R U . . . N00B N 0.9494(6) 0.8008(15) 0.7797(11) 0.067(6) Uani 1 1 d G . . . . C004 C 0.8828(9) 0.8171(14) 0.6572(10) 0.076(7) Uani 1 1 d G . . . . C00H C 0.7442(9) 0.8172(14) 0.6298(8) 0.068(6) Uani 1 1 d G . . . . C3 C -0.0802(9) 0.4431(13) 0.7948(15) 0.084(9) Uani 1 1 d G . . . . C00V C -0.1023(13) 0.4879(13) 0.6754(14) 0.084(7) Uani 1 1 d G . . . . H00V H -0.032894 0.488290 0.628050 0.101 Uiso 1 1 calc R U . . . C00Q C -0.2257(16) 0.5321(16) 0.6253(14) 0.095(8) Uani 1 1 d G . . . . H00Q H -0.240777 0.562725 0.543703 0.114 Uiso 1 1 calc R U . . . C00R C -0.3272(12) 0.5315(18) 0.6946(17) 0.118(11) Uani 1 1 d G . . . . H00R H -0.411615 0.561756 0.660352 0.142 Uiso 1 1 calc R U . . . C015 C -0.3052(11) 0.4867(16) 0.8140(17) 0.097(9) Uani 1 1 d G . . . . H015 H -0.374571 0.486351 0.861351 0.116 Uiso 1 1 calc R U . . . C00W C -0.1817(12) 0.4425(14) 0.8641(14) 0.117(13) Uani 1 1 d G . . . . H00W H -0.166688 0.411915 0.945701 0.141 Uiso 1 1 calc R U . . . P001 P 0.1564(8) 0.3920(10) 0.7947(10) 0.056(3) Uani 1 1 d . . . . . O1 O 0.2621(17) 0.877(2) 0.664(2) 0.090(7) Uani 1 1 d . . . . . H1C H 0.247870 0.910733 0.727027 0.135 Uiso 1 1 calc R U . . . N1 N 0.9505(19) 0.826(2) 0.572(2) 0.084(7) Uani 1 1 d . . . . . H1A H 0.910311 0.832461 0.493345 0.101 Uiso 1 1 calc R U . . . H1B H 1.038209 0.825783 0.591524 0.101 Uiso 1 1 calc R U . . . C1 C 0.5302(16) 0.823(2) 0.567(2) 0.079(8) Uani 1 1 d . . . . . H1 H 0.444933 0.831559 0.515205 0.094 Uiso 1 1 calc R U . . . O2 O 0.0261(14) 0.3992(19) 0.850(2) 0.085(6) Uani 1 1 d . . . . . O002 O 0.2144(18) 0.4988(18) 0.8403(18) 0.077(6) Uani 1 1 d . . . . . C2 C 0.4591(16) 0.781(2) 0.762(2) 0.067(6) Uani 1 1 d . . . . . O3 O 0.053(3) 0.160(2) 0.867(2) 0.102(8) Uani 1 1 d . . . . . O4 O 0.164(3) 0.039(5) 0.762(9) 0.28(4) Uani 1 1 d . . . . . C003 C 0.4760(15) 0.8548(15) 0.8672(19) 0.047(4) Uani 1 1 d . . . . . N4 N 0.245(2) 0.3011(16) 0.8793(16) 0.067(5) Uani 1 1 d . . . . . H4 H 0.283411 0.316750 0.956866 0.080 Uiso 1 1 calc R U . . . C4 C 0.390(2) 0.151(3) 0.905(3) 0.104(10) Uani 1 1 d . . . . . H4A H 0.391198 0.073424 0.893243 0.156 Uiso 1 1 calc R U . . . H4B H 0.394529 0.167301 0.994169 0.156 Uiso 1 1 calc R U . . . H4C H 0.465945 0.183542 0.876246 0.156 Uiso 1 1 calc R U . . . O5 O 0.4656(13) 0.6829(16) 0.8157(17) 0.062(4) Uani 1 1 d . . . . . O006 O 0.2020(18) 0.786(2) 0.8656(19) 0.103(9) Uani 1 1 d . . . . . H00I H 0.121263 0.800283 0.838695 0.154 Uiso 1 1 calc R U . . . C00C C 0.5527(14) 0.7995(17) 0.6840(17) 0.049(5) Uani 1 1 d . . . . . C00D C 0.2636(17) 0.196(2) 0.831(3) 0.090(8) Uani 1 1 d . . . . . H00D H 0.276226 0.203980 0.742491 0.108 Uiso 1 1 calc R U . . . N00F N 0.4949(16) 0.915(2) 0.9450(19) 0.070(6) Uani 1 1 d . . . . . C00G C 0.2441(16) 0.718(2) 0.789(3) 0.094(9) Uani 1 1 d . . . . . H00G H 0.166361 0.678109 0.740601 0.113 Uiso 1 1 calc R U . . . C00L C 0.3106(17) 0.7883(19) 0.6967(19) 0.064(6) Uani 1 1 d . . . . . H00L H 0.302634 0.745361 0.617916 0.077 Uiso 1 1 calc R U . . . C00N C 0.3438(17) 0.6424(19) 0.849(2) 0.070(7) Uani 1 1 d . . . . . H00N H 0.349989 0.642205 0.942280 0.084 Uiso 1 1 calc R U . . . C00P C 0.6557(19) 0.833(2) 0.528(2) 0.076(7) Uani 1 1 d . . . . . H00P H 0.671168 0.848893 0.446260 0.091 Uiso 1 1 calc R U . . . C00T C -0.290(2) 0.074(4) 0.752(3) 0.139(16) Uani 1 1 d . . . . . H00A H -0.294193 0.047036 0.836643 0.167 Uiso 1 1 calc R U . . . H00B H -0.278322 0.011967 0.698143 0.167 Uiso 1 1 calc R U . . . C00U C 0.3248(18) 0.537(2) 0.799(2) 0.068(6) Uani 1 1 d . . . . . H00C H 0.309531 0.539069 0.706574 0.081 Uiso 1 1 calc R U . . . H00E H 0.403749 0.492250 0.830635 0.081 Uiso 1 1 calc R U . . . O00X O 0.1479(13) 0.368(2) 0.671(2) 0.094(9) Uani 1 1 d . . . . . C00Y C 0.150(3) 0.127(3) 0.830(3) 0.110(11) Uani 1 1 d . . . . . C00Z C -0.139(3) 0.185(3) 0.660(3) 0.099(9) Uani 1 1 d . . . . . H00F H -0.051501 0.220248 0.684168 0.118 Uiso 1 1 calc R U . . . H00H H -0.204466 0.240093 0.621432 0.118 Uiso 1 1 calc R U . . . C010 C -0.176(2) 0.147(2) 0.759(3) 0.081(7) Uani 1 1 d . . . . . H010 H -0.198777 0.210425 0.806436 0.097 Uiso 1 1 calc R U . . . C011 C -0.130(3) 0.092(2) 0.557(3) 0.102(9) Uani 1 1 d . . . . . H01A H -0.090235 0.122509 0.488581 0.153 Uiso 1 1 calc R U . . . H01B H -0.219035 0.065178 0.522599 0.153 Uiso 1 1 calc R U . . . H01C H -0.073460 0.033848 0.596899 0.153 Uiso 1 1 calc R U . . . C012 C -0.062(4) 0.088(3) 0.850(3) 0.130(14) Uani 1 1 d . . . . . H01D H -0.089044 0.074132 0.931768 0.156 Uiso 1 1 calc R U . . . H01E H -0.040248 0.019293 0.814078 0.156 Uiso 1 1 calc R U . . . C013 C -0.433(6) 0.137(6) 0.692(5) 0.24(4) Uani 1 1 d . . . . . H01F H -0.418083 0.187454 0.626381 0.367 Uiso 1 1 calc R U . . . H01G H -0.464964 0.176882 0.758540 0.367 Uiso 1 1 calc R U . . . H01H H -0.500791 0.084629 0.655339 0.367 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 N2 0.054(9) 0.066(15) 0.074(12) 0.041(10) 0.015(9) 0.006(9) N3 0.021(6) 0.096(17) 0.093(14) 0.000(11) 0.013(7) -0.007(8) C00K 0.049(9) 0.08(2) 0.094(16) 0.044(14) -0.016(10) 0.001(11) N00B 0.064(9) 0.062(15) 0.078(12) 0.046(10) 0.020(9) 0.031(9) C004 0.028(8) 0.09(2) 0.124(19) 0.029(14) 0.038(11) -0.005(10) C00H 0.020(7) 0.10(2) 0.073(13) 0.019(11) -0.008(8) 0.011(9) C3 0.044(11) 0.08(2) 0.13(2) 0.077(16) 0.033(12) 0.009(10) C00V 0.073(13) 0.09(2) 0.10(2) -0.020(14) 0.030(13) -0.009(13) C00Q 0.095(16) 0.08(2) 0.11(2) -0.001(14) 0.023(16) 0.020(15) C00R 0.090(18) 0.08(3) 0.19(3) -0.04(2) 0.04(2) 0.038(17) C015 0.059(12) 0.11(3) 0.13(2) 0.001(18) 0.050(14) 0.036(14) C00W 0.030(9) 0.17(3) 0.15(3) -0.09(2) 0.020(13) -0.006(13) P001 0.033(4) 0.078(9) 0.056(7) -0.028(5) 0.008(4) -0.001(5) O1 0.045(8) 0.12(2) 0.095(15) 0.025(13) -0.009(9) -0.006(11) N1 0.052(9) 0.11(2) 0.095(15) -0.016(12) 0.023(10) -0.025(11) C1 0.030(8) 0.11(2) 0.082(17) 0.030(13) -0.017(9) 0.006(10) O2 0.031(7) 0.089(16) 0.143(18) 0.010(12) 0.040(9) -0.004(9) O002 0.073(10) 0.080(17) 0.069(13) -0.019(9) -0.009(9) 0.027(10) C2 0.029(8) 0.065(19) 0.099(16) 0.031(13) -0.009(9) 0.013(9) O3 0.130(19) 0.076(19) 0.110(18) 0.001(13) 0.049(15) -0.017(16) O4 0.067(16) 0.18(5) 0.62(12) -0.15(7) 0.09(3) -0.02(2) C003 0.041(8) 0.033(13) 0.065(13) -0.012(10) 0.009(8) -0.005(7) N4 0.098(12) 0.058(14) 0.046(9) -0.030(8) 0.018(8) -0.019(11) C4 0.062(12) 0.09(3) 0.15(3) 0.016(16) 0.000(14) 0.042(14) O5 0.035(6) 0.075(14) 0.078(11) 0.017(9) 0.019(7) 0.004(7) O006 0.053(9) 0.17(3) 0.091(14) 0.047(14) 0.015(10) 0.071(14) C00C 0.029(8) 0.066(14) 0.057(12) 0.012(9) 0.018(8) -0.012(8) C00D 0.034(9) 0.09(2) 0.15(2) 0.008(16) 0.037(11) 0.008(11) N00F 0.049(9) 0.091(19) 0.068(14) -0.016(11) 0.008(9) -0.012(9) C00G 0.014(7) 0.10(2) 0.17(3) 0.039(17) 0.040(11) 0.007(10) C00L 0.059(10) 0.058(16) 0.062(12) 0.036(10) -0.026(9) 0.000(11) C00N 0.043(9) 0.07(2) 0.093(17) -0.029(12) -0.003(10) 0.017(10) C00P 0.058(11) 0.09(2) 0.082(15) 0.017(12) 0.013(11) -0.025(11) C00T 0.051(12) 0.23(5) 0.14(3) 0.08(3) 0.017(15) -0.010(19) C00U 0.046(9) 0.083(19) 0.081(15) 0.003(12) 0.029(9) -0.004(10) O00X 0.032(6) 0.11(2) 0.15(2) -0.073(15) 0.031(9) -0.016(9) C00Y 0.082(18) 0.15(3) 0.09(2) -0.015(18) 0.014(15) 0.06(2) C00Z 0.080(15) 0.09(3) 0.13(3) 0.005(18) 0.018(15) -0.033(15) C010 0.071(13) 0.06(2) 0.11(2) 0.009(13) -0.001(14) -0.003(12) C011 0.073(13) 0.09(3) 0.15(3) 0.021(17) 0.034(16) 0.007(14) C012 0.21(3) 0.08(3) 0.072(18) -0.034(14) -0.024(19) -0.08(2) C013 0.26(6) 0.23(8) 0.22(6) 0.02(4) -0.02(5) -0.18(6) 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 C00C N2 N3 128.6(11) . . ? C00C N2 C00H 111.3(12) . . ? N3 N2 C00H 120.0 . . ? C00K N3 N2 120.0 . . ? N3 C00K N00B 120.0 . . ? C004 N00B C00K 120.0 . . ? N1 C004 C00H 121.5(13) . . ? N1 C004 N00B 118.4(13) . . ? C00H C004 N00B 120.0 . . ? C00P C00H C004 134.1(12) . . ? C00P C00H N2 105.9(12) . . ? C004 C00H N2 120.0 . . ? O2 C3 C00V 126.4(13) . . ? O2 C3 C00W 113.6(13) . . ? C00V C3 C00W 120.0 . . ? O2 C3 P001 31.3(10) . . ? C00V C3 P001 95.1(8) . . ? C00W C3 P001 144.9(7) . . ? C00Q C00V C3 120.0 . . ? C00Q C00V P001 177.1(5) . . ? C3 C00V P001 57.1(7) . . ? C00R C00Q C00V 120.0 . . ? C00Q C00R C015 120.0 . . ? C00W C015 C00R 120.0 . . ? C015 C00W C3 120.0 . . ? O00X P001 O002 118.1(16) . . ? O00X P001 O2 119.5(13) . . ? O002 P001 O2 97.6(12) . . ? O00X P001 N4 109.0(14) . . ? O002 P001 N4 106.9(13) . . ? O2 P001 N4 104.3(13) . . ? O00X P001 C00U 95.7(13) . . ? O002 P001 C00U 28.5(9) . . ? O2 P001 C00U 125.7(12) . . ? N4 P001 C00U 100.8(11) . . ? O00X P001 C3 100.1(10) . . ? O002 P001 C3 95.4(10) . . ? O2 P001 C3 24.8(9) . . ? N4 P001 C3 127.9(10) . . ? C00U P001 C3 118.5(9) . . ? O00X P001 C00D 83.6(14) . . ? O002 P001 C00D 129.6(11) . . ? O2 P001 C00D 110.4(11) . . ? N4 P001 C00D 27.1(9) . . ? C00U P001 C00D 113.7(9) . . ? C3 P001 C00D 126.9(7) . . ? O00X P001 C00V 76.9(11) . . ? O002 P001 C00V 92.8(11) . . ? O2 P001 C00V 52.7(10) . . ? N4 P001 C00V 152.2(9) . . ? C00U P001 C00V 105.6(9) . . ? C3 P001 C00V 27.8(3) . . ? C00D P001 C00V 137.5(7) . . ? C00C C1 C00P 108.1(17) . . ? C3 O2 P001 123.8(18) . . ? C00U O002 P001 120.1(16) . . ? O5 C2 C00C 115.2(18) . . ? O5 C2 C003 104(2) . . ? C00C C2 C003 112(2) . . ? O5 C2 C00L 102.5(17) . . ? C00C C2 C00L 115.9(18) . . ? C003 C2 C00L 106.2(19) . . ? C00Y O3 C012 116(3) . . ? N00F C003 C2 175(2) . . ? C00D N4 P001 122.0(17) . . ? C2 O5 C00N 116.7(15) . . ? N2 C00C C1 109.8(14) . . ? N2 C00C C2 122.1(17) . . ? C1 C00C C2 128.0(16) . . ? C00Y C00D N4 113(2) . . ? C00Y C00D C4 114(3) . . ? N4 C00D C4 108(2) . . ? C00Y C00D P001 103.5(17) . . ? N4 C00D P001 30.9(11) . . ? C4 C00D P001 135(2) . . ? O006 C00G C00N 115(2) . . ? O006 C00G C00L 106(3) . . ? C00N C00G C00L 107.3(16) . . ? O1 C00L C2 119(2) . . ? O1 C00L C00G 119(2) . . ? C2 C00L C00G 100.3(15) . . ? C00U C00N C00G 113(2) . . ? C00U C00N O5 106.8(16) . . ? C00G C00N O5 103(2) . . ? C00H C00P C1 104.6(18) . . ? C010 C00T C013 111(3) . . ? O002 C00U C00N 105.3(18) . . ? O002 C00U P001 31.5(10) . . ? C00N C00U P001 136.5(14) . . ? O3 C00Y O4 130(4) . . ? O3 C00Y C00D 121(3) . . ? O4 C00Y C00D 109(3) . . ? C010 C00Z C011 112(3) . . ? C00Z C010 C00T 122(3) . . ? C00Z C010 C012 114(3) . . ? C00T C010 C012 104(2) . . ? O3 C012 C010 106(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 N2 C00C 1.218(18) . ? N2 N3 1.3900 . ? N2 C00H 1.3900 . ? N3 C00K 1.3900 . ? C00K N00B 1.3900 . ? N00B C004 1.3900 . ? C004 N1 1.26(2) . ? C004 C00H 1.3900 . ? C00H C00P 1.30(3) . ? C3 O2 1.26(2) . ? C3 C00V 1.3900 . ? C3 C00W 1.3900 . ? C3 P001 2.500(15) . ? C00V C00Q 1.3900 . ? C00V P001 2.97(2) . ? C00Q C00R 1.3900 . ? C00R C015 1.3900 . ? C015 C00W 1.3900 . ? P001 O00X 1.36(3) . ? P001 O002 1.50(3) . ? P001 O2 1.565(19) . ? P001 N4 1.63(3) . ? P001 C00U 2.50(3) . ? P001 C00D 2.69(4) . ? O1 C00L 1.24(3) . ? C1 C00C 1.28(3) . ? C1 C00P 1.43(3) . ? O002 C00U 1.37(3) . ? C2 O5 1.35(3) . ? C2 C00C 1.41(3) . ? C2 C003 1.46(3) . ? C2 C00L 1.55(2) . ? O3 C00Y 1.21(4) . ? O3 C012 1.46(4) . ? O4 C00Y 1.34(6) . ? C003 N00F 1.12(3) . ? N4 C00D 1.44(4) . ? C4 C00D 1.49(3) . ? O5 C00N 1.45(3) . ? O006 C00G 1.31(4) . ? C00D C00Y 1.44(5) . ? C00G C00N 1.45(3) . ? C00G C00L 1.58(3) . ? C00N C00U 1.42(3) . ? C00T C010 1.46(4) . ? C00T C013 1.68(8) . ? C00Z C010 1.30(3) . ? C00Z C011 1.62(4) . ? C010 C012 1.56(4) . ? 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 O1 H1C O4 0.84 1.89 2.58(6) 138.2 1_565 yes N1 H1B O1 0.88 2.36 3.21(3) 162.9 1_655 yes N1 H1A O00X 0.88 1.83 2.69(4) 168.2 2_656 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 C00C N2 N3 C00K 177(2) . . . . ? C00H N2 N3 C00K 0.0 . . . . ? N2 N3 C00K N00B 0.0 . . . . ? N3 C00K N00B C004 0.0 . . . . ? C00K N00B C004 N1 -176.4(17) . . . . ? C00K N00B C004 C00H 0.0 . . . . ? N1 C004 C00H C00P -7(3) . . . . ? N00B C004 C00H C00P 177(2) . . . . ? N1 C004 C00H N2 176.3(17) . . . . ? N00B C004 C00H N2 0.0 . . . . ? C00C N2 C00H C00P 4.7(18) . . . . ? N3 N2 C00H C00P -177.9(18) . . . . ? C00C N2 C00H C004 -177.4(17) . . . . ? N3 N2 C00H C004 0.0 . . . . ? O2 C3 C00V C00Q 179(2) . . . . ? C00W C3 C00V C00Q 0.0 . . . . ? P001 C3 C00V C00Q -179.6(10) . . . . ? O2 C3 C00V P001 -1.4(16) . . . . ? C00W C3 C00V P001 179.6(10) . . . . ? C3 C00V C00Q C00R 0.0 . . . . ? C00V C00Q C00R C015 0.0 . . . . ? C00Q C00R C015 C00W 0.0 . . . . ? C00R C015 C00W C3 0.0 . . . . ? O2 C3 C00W C015 -179(2) . . . . ? C00V C3 C00W C015 0.0 . . . . ? P001 C3 C00W C015 179.3(18) . . . . ? C00V C3 O2 P001 3(3) . . . . ? C00W C3 O2 P001 -178.3(14) . . . . ? O00X P001 O2 C3 -42(3) . . . . ? O002 P001 O2 C3 86(2) . . . . ? N4 P001 O2 C3 -164(2) . . . . ? C00U P001 O2 C3 81(3) . . . . ? C00D P001 O2 C3 -136(2) . . . . ? C00V P001 O2 C3 -1.3(14) . . . . ? O00X P001 O002 C00U -42(2) . . . . ? O2 P001 O002 C00U -171.0(19) . . . . ? N4 P001 O002 C00U 81(2) . . . . ? C3 P001 O002 C00U -146.1(17) . . . . ? C00D P001 O002 C00U 64(2) . . . . ? C00V P001 O002 C00U -118.3(18) . . . . ? O00X P001 N4 C00D -22(2) . . . . ? O002 P001 N4 C00D -150.3(18) . . . . ? O2 P001 N4 C00D 106.9(19) . . . . ? C00U P001 N4 C00D -121.7(17) . . . . ? C3 P001 N4 C00D 98.5(18) . . . . ? C00V P001 N4 C00D 76(2) . . . . ? C00C C2 O5 C00N -154.2(18) . . . . ? C003 C2 O5 C00N 83(2) . . . . ? C00L C2 O5 C00N -27(3) . . . . ? N3 N2 C00C C1 177.1(17) . . . . ? C00H N2 C00C C1 -6(2) . . . . ? N3 N2 C00C C2 1(3) . . . . ? C00H N2 C00C C2 177.9(18) . . . . ? C00P C1 C00C N2 4(3) . . . . ? C00P C1 C00C C2 -179(2) . . . . ? O5 C2 C00C N2 -64(3) . . . . ? C003 C2 C00C N2 55(3) . . . . ? C00L C2 C00C N2 176(2) . . . . ? O5 C2 C00C C1 120(3) . . . . ? C003 C2 C00C C1 -121(3) . . . . ? C00L C2 C00C C1 1(4) . . . . ? P001 N4 C00D C00Y -78(3) . . . . ? P001 N4 C00D C4 155.9(19) . . . . ? O5 C2 C00L O1 163(2) . . . . ? C00C C2 C00L O1 -71(3) . . . . ? C003 C2 C00L O1 54(3) . . . . ? O5 C2 C00L C00G 31(3) . . . . ? C00C C2 C00L C00G 157(2) . . . . ? C003 C2 C00L C00G -78(2) . . . . ? O006 C00G C00L O1 -35(3) . . . . ? C00N C00G C00L O1 -158(2) . . . . ? O006 C00G C00L C2 97(2) . . . . ? C00N C00G C00L C2 -26(3) . . . . ? O006 C00G C00N C00U 140(2) . . . . ? C00L C00G C00N C00U -103(2) . . . . ? O006 C00G C00N O5 -105(2) . . . . ? C00L C00G C00N O5 12(3) . . . . ? C2 O5 C00N C00U 130(2) . . . . ? C2 O5 C00N C00G 10(3) . . . . ? C004 C00H C00P C1 -179.2(16) . . . . ? N2 C00H C00P C1 -2(2) . . . . ? C00C C1 C00P C00H -1(3) . . . . ? P001 O002 C00U C00N 174.1(17) . . . . ? C00G C00N C00U O002 -71(3) . . . . ? O5 C00N C00U O002 175.8(17) . . . . ? C00G C00N C00U P001 -67(3) . . . . ? O5 C00N C00U P001 -179.7(17) . . . . ? C012 O3 C00Y O4 8(8) . . . . ? C012 O3 C00Y C00D 174(3) . . . . ? N4 C00D C00Y O3 -1(4) . . . . ? C4 C00D C00Y O3 122(3) . . . . ? P001 C00D C00Y O3 -32(3) . . . . ? N4 C00D C00Y O4 168(5) . . . . ? C4 C00D C00Y O4 -69(5) . . . . ? P001 C00D C00Y O4 137(5) . . . . ? C011 C00Z C010 C00T -48(4) . . . . ? C011 C00Z C010 C012 78(3) . . . . ? C013 C00T C010 C00Z -66(5) . . . . ? C013 C00T C010 C012 164(3) . . . . ? C00Y O3 C012 C010 -116(3) . . . . ? C00Z C010 C012 O3 48(3) . . . . ? C00T C010 C012 O3 -177(3) . . . . ?