#------------------------------------------------------------------------------ #$Date: 2020-02-05 04:13:59 +0200 (Wed, 05 Feb 2020) $ #$Revision: 247875 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557237.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_1557237 loop_ _publ_author_name 'Navarro, Miquel' 'Toledo, Alberto' 'Ladeira, Sonia' 'Sosa Carrizo, E. Daiann' 'Miqueu, Karinne' 'Bourissou, Didier' _publ_section_title ; Versatility and Adaptative Behaviour of the P^N Chelating Ligand MeDalphos within Gold(I) pi Complexes: ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC06398F _journal_year 2020 _chemical_formula_sum 'C21 H20 N4 O5' _chemical_formula_weight 408.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary 'Dual space' _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-11-25 deposited with the CCDC. 2020-01-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.515(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.4212(12) _cell_length_b 13.4652(8) _cell_length_c 9.4134(7) _cell_measurement_reflns_used 5737 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 25.15 _cell_measurement_theta_min 2.68 _cell_volume 1908.2(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (Sheldrick 2015)' _diffrn_ambient_temperature 193(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker kappa APEX-II CCD Quazar' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1385 _diffrn_reflns_av_unetI/netI 0.0785 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 43146 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.271 _diffrn_reflns_theta_min 3.215 _diffrn_source 'Incoatec microfocus sealed tube' _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.422 _exptl_crystal_description needle _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.234 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 317 _refine_ls_number_reflns 3452 _refine_ls_number_restraints 149 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.1430 _refine_ls_R_factor_gt 0.0611 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0913P)^2^+0.0670P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1452 _refine_ls_wR_factor_ref 0.1833 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1836 _reflns_number_total 3452 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06398f2.cif _cod_data_source_block MNB030919_a _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557237 _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_estimated_absorpt_t_min 0.980 _shelx_estimated_absorpt_t_max 0.997 _shelx_res_file ; TITL MNB030919_a.res in P2(1)/c MNB030919_a.res created by SHELXL-2018/3 at 12:42:46 on 06-Sep-2019 CELL 0.71073 15.4212 13.4652 9.4134 90.000 102.515 90.000 ZERR 4.000 0.0012 0.0008 0.0007 0.000 0.004 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 84 80 16 20 OMIT 0 1 1 OMIT 2 0 0 L.S. 10 SHEL 10 0.83 ACTA EQIV $1 -x, y+1/2, -z+1/2 HTAB O1 O4_$1 EQIV $3 -x+1, -y, -z+1 HTAB N1 O2_$3 EQIV $4 x, y, z+1 HTAB N3 O1_$4 SADI 0.01 C6 C5 C6 C5' SADI 0.01 C14 C5 C14 C5' BOND $H EXYZ C1 C1' EADP C1 C1' DELU O1 > C5' SIMU 0.01 O1 > C5' FMAP 2 PLAN 20 SIZE 0.03 0.05 0.20 TEMP -80.150 SAME O1 C1' > C5' WGHT 0.091300 0.067000 FVAR 0.15154 0.85058 O1 4 0.201987 0.677988 -0.211372 11.00000 0.07781 0.05118 = 0.03810 -0.00496 0.01312 0.02052 H1E 2 0.154777 0.713393 -0.222064 11.00000 -1.50000 PART 1 21 C1 1 0.256088 0.689047 -0.070095 21.00000 0.07351 0.04502 = 0.04468 -0.00601 0.00977 0.00995 AFIX 23 H1A 2 0.225984 0.732472 -0.010895 21.00000 -1.20000 H1B 2 0.313124 0.720531 -0.076524 21.00000 -1.20000 AFIX 0 C2 1 0.273492 0.587723 0.001891 21.00000 0.06135 0.03993 = 0.04829 0.00267 0.00974 0.00917 AFIX 23 H2A 2 0.296727 0.543378 -0.065069 21.00000 -1.20000 H2B 2 0.320918 0.595312 0.090768 21.00000 -1.20000 AFIX 0 C3 1 0.197703 0.538143 0.042612 21.00000 0.05628 0.04523 = 0.03579 0.00250 0.00948 0.01074 AFIX 23 H3A 2 0.147028 0.538732 -0.042398 21.00000 -1.20000 H3B 2 0.179997 0.576909 0.121084 21.00000 -1.20000 AFIX 0 C4 1 0.215299 0.430759 0.094351 21.00000 0.04705 0.04330 = 0.03063 0.00120 0.00609 -0.00026 AFIX 23 H4A 2 0.239913 0.393569 0.021352 21.00000 -1.20000 H4B 2 0.158255 0.399286 0.100763 21.00000 -1.20000 AFIX 0 C5 1 0.280014 0.422727 0.242882 21.00000 0.04119 0.02986 = 0.02603 -0.00197 0.00214 -0.00437 AFIX 13 H5 2 0.333310 0.464096 0.239035 21.00000 -1.20000 AFIX 0 PART 2 -21 C1' 1 0.256088 0.689047 -0.070095 -21.00000 0.07351 0.04502 = 0.04468 -0.00601 0.00977 0.00995 AFIX 23 H1C 2 0.217552 0.707862 -0.002918 -21.00000 -1.20000 H1D 2 0.297646 0.744805 -0.072123 -21.00000 -1.20000 AFIX 0 C2' 1 0.307499 0.602645 -0.010868 -21.00000 0.06743 0.04797 = 0.04554 -0.00022 0.01454 0.01343 AFIX 23 H2C 2 0.371604 0.618634 0.017054 -21.00000 -1.20000 H2D 2 0.298672 0.547430 -0.081996 -21.00000 -1.20000 AFIX 0 C3' 1 0.272217 0.577081 0.117478 -21.00000 0.06444 0.04541 = 0.04479 0.00093 0.01700 0.01500 AFIX 23 H3C 2 0.207256 0.566189 0.089473 -21.00000 -1.20000 H3D 2 0.284195 0.631240 0.190228 -21.00000 -1.20000 AFIX 0 C4' 1 0.319606 0.481732 0.180127 -21.00000 0.05425 0.03935 = 0.03185 -0.00277 0.01736 0.01018 AFIX 23 H4C 2 0.368758 0.498732 0.263074 -21.00000 -1.20000 H4D 2 0.345605 0.449098 0.104784 -21.00000 -1.20000 AFIX 0 C5' 1 0.256137 0.409356 0.231620 -21.00000 0.05025 0.03517 = 0.02748 -0.00550 0.00760 0.00096 AFIX 13 H5' 2 0.200618 0.396000 0.156809 -21.00000 -1.20000 AFIX 0 PART 0 O2 4 0.560675 0.049162 0.727143 11.00000 0.09589 0.04117 = 0.05716 0.00038 -0.01079 0.02288 O3 4 0.608637 0.190373 0.820024 11.00000 0.06400 0.06228 = 0.04678 -0.00498 -0.01238 0.00944 O4 4 -0.065177 0.284614 0.636810 11.00000 0.06160 0.14108 = 0.09818 0.03811 0.01746 -0.03038 O5 4 -0.018554 0.405181 0.781764 11.00000 0.09938 0.10491 = 0.09134 0.02655 0.06196 0.02029 N1 3 0.327820 0.152389 0.280374 11.00000 0.05486 0.02623 = 0.03062 -0.00721 0.00429 0.00134 H1 2 0.324497 0.100439 0.249486 11.00000 -1.20000 N2 3 0.559899 0.140432 0.726584 11.00000 0.05251 0.05037 = 0.03983 -0.00154 0.00402 0.01286 N3 3 0.224382 0.553772 0.557256 11.00000 0.05679 0.03040 = 0.03360 -0.00997 0.00996 -0.00029 H3 2 0.230647 0.595863 0.625036 11.00000 -1.20000 N4 3 -0.016438 0.356498 0.673495 11.00000 0.05094 0.09094 = 0.06829 0.03596 0.01348 0.01668 C6 1 0.311370 0.317287 0.278536 11.00000 0.03995 0.03035 = 0.02555 -0.00171 0.00710 0.00289 C7 1 0.282303 0.230927 0.209612 11.00000 0.04576 0.03490 = 0.02949 -0.00233 0.00655 0.00175 AFIX 43 H7 2 0.236644 0.226082 0.124089 11.00000 -1.20000 AFIX 0 C8 1 0.388757 0.186670 0.397099 11.00000 0.03699 0.02933 = 0.02621 -0.00181 0.00860 0.00362 C9 1 0.380312 0.291063 0.398892 11.00000 0.03907 0.02704 = 0.02571 -0.00023 0.01265 -0.00013 C10 1 0.436084 0.344776 0.510179 11.00000 0.04643 0.02759 = 0.03221 -0.00250 0.00865 -0.00039 AFIX 43 H10 2 0.432599 0.415181 0.512320 11.00000 -1.20000 AFIX 0 C11 1 0.495045 0.295757 0.614784 11.00000 0.04073 0.04054 = 0.02797 -0.00404 0.00560 0.00150 AFIX 43 H11 2 0.532983 0.331562 0.690545 11.00000 -1.20000 AFIX 0 C12 1 0.499442 0.191900 0.610007 11.00000 0.03863 0.03855 = 0.03205 0.00057 0.00627 0.00841 C13 1 0.448007 0.136115 0.502782 11.00000 0.04681 0.03205 = 0.03591 -0.00292 0.01235 0.00791 AFIX 43 H13 2 0.452892 0.065812 0.501224 11.00000 -1.20000 AFIX 0 C14 1 0.239889 0.462381 0.365520 11.00000 0.04911 0.02525 = 0.02400 0.00075 0.00120 0.00305 C15 1 0.270509 0.541597 0.451028 11.00000 0.05154 0.02811 = 0.03292 -0.00074 0.00476 0.00001 AFIX 43 H15 2 0.318036 0.583089 0.438152 11.00000 -1.20000 AFIX 0 C16 1 0.168609 0.422696 0.420927 11.00000 0.04246 0.03014 = 0.02636 0.00546 -0.00096 0.00400 C17 1 0.160917 0.481704 0.542211 11.00000 0.03903 0.03246 = 0.03370 0.00651 0.00294 0.01066 C18 1 0.100748 0.462035 0.625860 11.00000 0.04804 0.04588 = 0.04013 0.00936 0.00993 0.01559 AFIX 43 H18 2 0.096235 0.502221 0.706892 11.00000 -1.20000 AFIX 0 C19 1 0.047326 0.380980 0.586021 11.00000 0.03897 0.06355 = 0.04684 0.02506 0.01239 0.00911 C20 1 0.050957 0.321227 0.467237 11.00000 0.05136 0.05141 = 0.04673 0.01200 -0.00265 -0.00968 AFIX 43 H20 2 0.011444 0.266632 0.443574 11.00000 -1.20000 AFIX 0 C21 1 0.111301 0.341108 0.384788 11.00000 0.05092 0.04154 = 0.03530 0.00135 0.00072 -0.00519 AFIX 43 H21 2 0.114618 0.300309 0.303803 11.00000 -1.20000 AFIX 0 HKLF 4 REM MNB030919_a.res in P2(1)/c REM wR2 = 0.183306, GooF = S = 1.05291, Restrained GooF = 1.04560 for all data REM R1 = 0.061052 for 1836 Fo > 4sig(Fo) and 0.143031 for all 3452 data REM 317 parameters refined using 149 restraints END WGHT 0.0913 0.0670 REM Highest difference peak 0.234, deepest hole -0.252, 1-sigma level 0.067 Q1 1 0.3112 0.0426 0.2563 11.00000 0.05 0.23 Q2 1 0.4204 0.3254 0.6051 11.00000 0.05 0.23 Q3 1 0.2053 0.5833 -0.0486 11.00000 0.05 0.23 Q4 1 0.2850 0.1249 0.1460 11.00000 0.05 0.23 Q5 1 0.3838 0.1268 0.1515 11.00000 0.05 0.23 Q6 1 0.3422 0.0897 0.2198 11.00000 0.05 0.22 Q7 1 0.4421 0.3798 0.5020 11.00000 0.05 0.22 Q8 1 0.3410 0.0605 0.1213 11.00000 0.05 0.22 Q9 1 0.4003 0.4371 0.5328 11.00000 0.05 0.22 Q10 1 0.3232 0.1175 0.2983 11.00000 0.05 0.20 Q11 1 0.1986 0.1716 0.2426 11.00000 0.05 0.19 Q12 1 0.3278 0.6039 0.1344 11.00000 0.05 0.19 Q13 1 0.0807 0.4136 0.0717 11.00000 0.05 0.19 Q14 1 0.3664 0.3722 0.5585 11.00000 0.05 0.19 Q15 1 0.3221 0.1363 0.1716 11.00000 0.05 0.19 Q16 1 0.0179 0.4283 0.9966 11.00000 0.05 0.18 Q17 1 0.0634 0.4005 0.9291 11.00000 0.05 0.18 Q18 1 0.4312 0.1168 0.2855 11.00000 0.05 0.18 Q19 1 -0.0878 0.3320 0.7507 11.00000 0.05 0.18 Q20 1 0.3595 0.5043 0.5123 11.00000 0.05 0.18 ; _shelx_res_checksum 30350 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0.20199(19) 0.67799(19) -0.2114(3) 0.0556(8) Uani 1 1 d D U . . . H1E H 0.155(3) 0.713(3) -0.222(5) 0.083 Uiso 1 1 d . U . . . C1 C 0.2561(3) 0.6890(3) -0.0701(4) 0.0549(10) Uani 0.851(4) 1 d D U P A 1 H1A H 0.225984 0.732472 -0.010895 0.066 Uiso 0.851(4) 1 calc R U P A 1 H1B H 0.313124 0.720531 -0.076524 0.066 Uiso 0.851(4) 1 calc R U P A 1 C2 C 0.2735(3) 0.5877(3) 0.0019(6) 0.0502(13) Uani 0.851(4) 1 d D U P A 1 H2A H 0.296727 0.543378 -0.065069 0.060 Uiso 0.851(4) 1 calc R U P A 1 H2B H 0.320918 0.595312 0.090768 0.060 Uiso 0.851(4) 1 calc R U P A 1 C3 C 0.1977(3) 0.5381(3) 0.0426(5) 0.0458(11) Uani 0.851(4) 1 d D U P A 1 H3A H 0.147028 0.538732 -0.042398 0.055 Uiso 0.851(4) 1 calc R U P A 1 H3B H 0.179997 0.576909 0.121084 0.055 Uiso 0.851(4) 1 calc R U P A 1 C4 C 0.2153(3) 0.4308(3) 0.0944(4) 0.0407(11) Uani 0.851(4) 1 d D U P A 1 H4A H 0.239913 0.393569 0.021352 0.049 Uiso 0.851(4) 1 calc R U P A 1 H4B H 0.158255 0.399286 0.100763 0.049 Uiso 0.851(4) 1 calc R U P A 1 C5 C 0.2800(3) 0.4227(3) 0.2429(4) 0.0331(12) Uani 0.851(4) 1 d D U P A 1 H5 H 0.333310 0.464096 0.239035 0.040 Uiso 0.851(4) 1 calc R U P A 1 C1' C 0.2561(3) 0.6890(3) -0.0701(4) 0.0549(10) Uani 0.149(4) 1 d D U P A 2 H1C H 0.217552 0.707862 -0.002918 0.066 Uiso 0.149(4) 1 calc R U P A 2 H1D H 0.297646 0.744805 -0.072123 0.066 Uiso 0.149(4) 1 calc R U P A 2 C2' C 0.3075(19) 0.6026(19) -0.011(3) 0.053(3) Uani 0.149(4) 1 d D U P A 2 H2C H 0.371604 0.618634 0.017054 0.064 Uiso 0.149(4) 1 calc R U P A 2 H2D H 0.298672 0.547430 -0.081996 0.064 Uiso 0.149(4) 1 calc R U P A 2 C3' C 0.2722(17) 0.5771(15) 0.117(3) 0.051(3) Uani 0.149(4) 1 d D U P A 2 H3C H 0.207256 0.566189 0.089473 0.061 Uiso 0.149(4) 1 calc R U P A 2 H3D H 0.284195 0.631240 0.190228 0.061 Uiso 0.149(4) 1 calc R U P A 2 C4' C 0.3196(14) 0.4817(13) 0.180(2) 0.041(3) Uani 0.149(4) 1 d D U P A 2 H4C H 0.368758 0.498732 0.263074 0.049 Uiso 0.149(4) 1 calc R U P A 2 H4D H 0.345605 0.449098 0.104784 0.049 Uiso 0.149(4) 1 calc R U P A 2 C5' C 0.2561(16) 0.4094(11) 0.2316(13) 0.038(3) Uani 0.149(4) 1 d D U P A 2 H5' H 0.200618 0.396000 0.156809 0.045 Uiso 0.149(4) 1 calc R U P A 2 O2 O 0.56067(19) 0.04916(19) 0.7271(3) 0.0689(9) Uani 1 1 d . . . . . O3 O 0.60864(18) 0.1904(2) 0.8200(3) 0.0614(8) Uani 1 1 d . . . . . O4 O -0.0652(2) 0.2846(3) 0.6368(4) 0.1003(13) Uani 1 1 d . . . . . O5 O -0.0186(2) 0.4052(3) 0.7818(5) 0.0923(11) Uani 1 1 d . . . . . N1 N 0.3278(2) 0.1524(2) 0.2804(3) 0.0380(8) Uani 1 1 d . . . . . H1 H 0.324(2) 0.100(3) 0.249(4) 0.046 Uiso 1 1 d . U . . . N2 N 0.5599(2) 0.1404(2) 0.7266(3) 0.0485(8) Uani 1 1 d . . . . . N3 N 0.2244(2) 0.5538(2) 0.5573(3) 0.0402(8) Uani 1 1 d . . . . . H3 H 0.231(2) 0.596(3) 0.625(4) 0.048 Uiso 1 1 d . U . . . N4 N -0.0164(3) 0.3565(3) 0.6735(5) 0.0700(11) Uani 1 1 d . . . . . C6 C 0.3114(2) 0.3173(2) 0.2785(3) 0.0319(8) Uani 1 1 d D . . . . C7 C 0.2823(2) 0.2309(2) 0.2096(4) 0.0370(9) Uani 1 1 d . . . . . H7 H 0.236644 0.226082 0.124089 0.044 Uiso 1 1 calc R U . . . C8 C 0.3888(2) 0.1867(2) 0.3971(3) 0.0306(8) Uani 1 1 d . . . . . C9 C 0.3803(2) 0.2911(2) 0.3989(3) 0.0298(8) Uani 1 1 d . . . . . C10 C 0.4361(2) 0.3448(2) 0.5102(3) 0.0354(8) Uani 1 1 d . . . . . H10 H 0.432599 0.415181 0.512320 0.042 Uiso 1 1 calc R U . . . C11 C 0.4950(2) 0.2958(2) 0.6148(3) 0.0367(8) Uani 1 1 d . . . . . H11 H 0.532983 0.331562 0.690545 0.044 Uiso 1 1 calc R U . . . C12 C 0.4994(2) 0.1919(2) 0.6100(4) 0.0366(8) Uani 1 1 d . . . . . C13 C 0.4480(2) 0.1361(2) 0.5028(4) 0.0377(9) Uani 1 1 d . . . . . H13 H 0.452892 0.065812 0.501224 0.045 Uiso 1 1 calc R U . . . C14 C 0.2399(2) 0.4624(2) 0.3655(3) 0.0338(8) Uani 1 1 d D . . . . C15 C 0.2705(2) 0.5416(2) 0.4510(4) 0.0382(9) Uani 1 1 d . . . . . H15 H 0.318036 0.583089 0.438152 0.046 Uiso 1 1 calc R U . . . C16 C 0.1686(2) 0.4227(2) 0.4209(3) 0.0343(8) Uani 1 1 d . . . . . C17 C 0.1609(2) 0.4817(2) 0.5422(4) 0.0358(8) Uani 1 1 d . . . . . C18 C 0.1007(2) 0.4620(3) 0.6259(4) 0.0446(9) Uani 1 1 d . . . . . H18 H 0.096235 0.502221 0.706892 0.054 Uiso 1 1 calc R U . . . C19 C 0.0473(2) 0.3810(3) 0.5860(4) 0.0493(10) Uani 1 1 d . . . . . C20 C 0.0510(3) 0.3212(3) 0.4672(4) 0.0518(10) Uani 1 1 d . . . . . H20 H 0.011444 0.266632 0.443574 0.062 Uiso 1 1 calc R U . . . C21 C 0.1113(2) 0.3411(2) 0.3848(4) 0.0439(9) Uani 1 1 d . . . . . H21 H 0.114618 0.300309 0.303803 0.053 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 0.078(2) 0.0512(16) 0.0381(15) -0.0050(12) 0.0131(14) 0.0205(13) C1 0.074(2) 0.0450(19) 0.045(2) -0.0060(16) 0.0098(18) 0.0100(17) C2 0.061(3) 0.040(2) 0.048(3) 0.0027(19) 0.010(2) 0.009(2) C3 0.056(3) 0.045(2) 0.036(2) 0.0025(18) 0.009(2) 0.011(2) C4 0.047(2) 0.043(2) 0.031(2) 0.0012(17) 0.0061(18) -0.0003(18) C5 0.041(3) 0.030(2) 0.026(2) -0.0020(16) 0.0021(18) -0.0044(19) C1' 0.074(2) 0.0450(19) 0.045(2) -0.0060(16) 0.0098(18) 0.0100(17) C2' 0.067(6) 0.048(5) 0.046(5) 0.000(5) 0.015(5) 0.013(5) C3' 0.064(5) 0.045(5) 0.045(5) 0.001(5) 0.017(5) 0.015(5) C4' 0.054(5) 0.039(5) 0.032(5) -0.003(5) 0.017(5) 0.010(5) C5' 0.050(6) 0.035(6) 0.027(6) -0.006(5) 0.008(6) 0.001(6) O2 0.096(2) 0.0412(17) 0.0572(19) 0.0004(13) -0.0108(16) 0.0229(14) O3 0.0640(19) 0.0623(17) 0.0468(17) -0.0050(14) -0.0124(14) 0.0094(14) O4 0.062(2) 0.141(3) 0.098(3) 0.038(2) 0.0175(19) -0.030(2) O5 0.099(3) 0.105(3) 0.091(3) 0.027(2) 0.062(2) 0.020(2) N1 0.0549(19) 0.0262(15) 0.0306(17) -0.0072(13) 0.0043(14) 0.0013(14) N2 0.053(2) 0.050(2) 0.040(2) -0.0015(16) 0.0040(16) 0.0129(16) N3 0.057(2) 0.0304(16) 0.0336(18) -0.0100(12) 0.0100(16) -0.0003(15) N4 0.051(2) 0.091(3) 0.068(3) 0.036(2) 0.013(2) 0.017(2) C6 0.040(2) 0.0304(18) 0.0255(19) -0.0017(14) 0.0071(16) 0.0029(15) C7 0.046(2) 0.0349(19) 0.029(2) -0.0023(15) 0.0066(16) 0.0017(16) C8 0.037(2) 0.0293(18) 0.0262(18) -0.0018(14) 0.0086(16) 0.0036(14) C9 0.039(2) 0.0270(18) 0.0257(18) -0.0002(14) 0.0127(15) -0.0001(14) C10 0.046(2) 0.0276(17) 0.032(2) -0.0025(15) 0.0086(17) -0.0004(15) C11 0.041(2) 0.041(2) 0.028(2) -0.0040(15) 0.0056(16) 0.0015(16) C12 0.039(2) 0.039(2) 0.032(2) 0.0006(16) 0.0063(16) 0.0084(16) C13 0.047(2) 0.0321(19) 0.036(2) -0.0029(15) 0.0123(18) 0.0079(16) C14 0.049(2) 0.0253(16) 0.0240(18) 0.0008(14) 0.0012(16) 0.0031(15) C15 0.052(2) 0.0281(18) 0.033(2) -0.0007(15) 0.0048(18) 0.0000(16) C16 0.042(2) 0.0301(18) 0.0264(19) 0.0055(14) -0.0010(16) 0.0040(15) C17 0.039(2) 0.0325(19) 0.034(2) 0.0065(15) 0.0029(17) 0.0107(16) C18 0.048(2) 0.046(2) 0.040(2) 0.0094(17) 0.0099(19) 0.0156(19) C19 0.039(2) 0.064(3) 0.047(3) 0.025(2) 0.0124(19) 0.009(2) C20 0.051(2) 0.051(2) 0.047(3) 0.012(2) -0.003(2) -0.0097(19) C21 0.051(2) 0.042(2) 0.035(2) 0.0014(17) 0.0007(19) -0.0052(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C1' O1 H1E 111(3) C1 O1 H1E 111(3) O1 C1 C2 109.6(3) O1 C1 H1A 109.8 C2 C1 H1A 109.8 O1 C1 H1B 109.8 C2 C1 H1B 109.8 H1A C1 H1B 108.2 C3 C2 C1 116.8(4) C3 C2 H2A 108.1 C1 C2 H2A 108.1 C3 C2 H2B 108.1 C1 C2 H2B 108.1 H2A C2 H2B 107.3 C2 C3 C4 114.6(3) C2 C3 H3A 108.6 C4 C3 H3A 108.6 C2 C3 H3B 108.6 C4 C3 H3B 108.6 H3A C3 H3B 107.6 C3 C4 C5 113.1(3) C3 C4 H4A 109.0 C5 C4 H4A 109.0 C3 C4 H4B 109.0 C5 C4 H4B 109.0 H4A C4 H4B 107.8 C6 C5 C14 108.9(3) C6 C5 C4 112.4(3) C14 C5 C4 112.1(3) C6 C5 H5 107.8 C14 C5 H5 107.8 C4 C5 H5 107.8 O1 C1' C2' 116.0(14) O1 C1' H1C 108.3 C2' C1' H1C 108.3 O1 C1' H1D 108.3 C2' C1' H1D 108.3 H1C C1' H1D 107.4 C1' C2' C3' 103.6(15) C1' C2' H2C 111.0 C3' C2' H2C 111.0 C1' C2' H2D 111.0 C3' C2' H2D 111.0 H2C C2' H2D 109.0 C2' C3' C4' 106.4(15) C2' C3' H3C 110.4 C4' C3' H3C 110.4 C2' C3' H3D 110.4 C4' C3' H3D 110.4 H3C C3' H3D 108.6 C3' C4' C5' 111.8(15) C3' C4' H4C 109.3 C5' C4' H4C 109.3 C3' C4' H4D 109.3 C5' C4' H4D 109.3 H4C C4' H4D 107.9 C6 C5' C14 109.1(7) C6 C5' C4' 104.8(14) C14 C5' C4' 101.3(15) C6 C5' H5' 113.6 C14 C5' H5' 113.6 C4' C5' H5' 113.6 C7 N1 C8 108.9(3) C7 N1 H1 123(3) C8 N1 H1 127(3) O3 N2 O2 122.8(3) O3 N2 C12 118.3(3) O2 N2 C12 119.0(3) C15 N3 C17 108.5(3) C15 N3 H3 130(2) C17 N3 H3 121(2) O5 N4 O4 122.2(4) O5 N4 C19 119.8(4) O4 N4 C19 117.9(4) C7 C6 C9 106.3(3) C7 C6 C5 129.8(3) C9 C6 C5 123.9(3) C7 C6 C5' 117.0(9) C9 C6 C5' 135.4(8) C6 C7 N1 110.4(3) C6 C7 H7 124.8 N1 C7 H7 124.8 N1 C8 C13 130.5(3) N1 C8 C9 107.3(3) C13 C8 C9 122.2(3) C10 C9 C8 118.6(3) C10 C9 C6 134.4(3) C8 C9 C6 107.0(3) C11 C10 C9 119.8(3) C11 C10 H10 120.1 C9 C10 H10 120.1 C10 C11 C12 119.4(3) C10 C11 H11 120.3 C12 C11 H11 120.3 C13 C12 C11 123.2(3) C13 C12 N2 118.1(3) C11 C12 N2 118.6(3) C12 C13 C8 116.8(3) C12 C13 H13 121.6 C8 C13 H13 121.6 C15 C14 C16 106.0(3) C15 C14 C5' 139.8(10) C16 C14 C5' 114.1(10) C15 C14 C5 125.4(3) C16 C14 C5 128.5(3) N3 C15 C14 111.2(3) N3 C15 H15 124.4 C14 C15 H15 124.4 C21 C16 C17 118.4(3) C21 C16 C14 134.6(3) C17 C16 C14 107.0(3) N3 C17 C18 129.8(3) N3 C17 C16 107.4(3) C18 C17 C16 122.8(3) C17 C18 C19 116.1(3) C17 C18 H18 122.0 C19 C18 H18 122.0 C18 C19 C20 123.7(3) C18 C19 N4 117.8(4) C20 C19 N4 118.4(4) C21 C20 C19 119.8(3) C21 C20 H20 120.1 C19 C20 H20 120.1 C20 C21 C16 119.2(3) C20 C21 H21 120.4 C16 C21 H21 120.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1' 1.416(4) O1 C1 1.416(4) O1 H1E 0.86(5) C1 C2 1.521(5) C1 H1A 0.9900 C1 H1B 0.9900 C2 C3 1.467(6) C2 H2A 0.9900 C2 H2B 0.9900 C3 C4 1.531(5) C3 H3A 0.9900 C3 H3B 0.9900 C4 C5 1.536(5) C4 H4A 0.9900 C4 H4B 0.9900 C5 C6 1.514(5) C5 C14 1.520(5) C5 H5 1.0000 C1' C2' 1.450(16) C1' H1C 0.9900 C1' H1D 0.9900 C2' C3' 1.469(19) C2' H2C 0.9900 C2' H2D 0.9900 C3' C4' 1.531(17) C3' H3C 0.9900 C3' H3D 0.9900 C4' C5' 1.532(19) C4' H4C 0.9900 C4' H4D 0.9900 C5' C6 1.515(10) C5' C14 1.516(10) C5' H5' 1.0000 O2 N2 1.229(4) O3 N2 1.226(4) O4 N4 1.228(5) O5 N4 1.218(5) N1 C7 1.361(4) N1 C8 1.362(4) N1 H1 0.76(3) N2 C12 1.453(4) N3 C15 1.357(4) N3 C17 1.364(4) N3 H3 0.84(3) N4 C19 1.451(5) C6 C7 1.359(4) C6 C9 1.420(4) C7 H7 0.9500 C8 C13 1.376(4) C8 C9 1.412(4) C9 C10 1.403(4) C10 C11 1.358(4) C10 H10 0.9500 C11 C12 1.401(4) C11 H11 0.9500 C12 C13 1.366(4) C13 H13 0.9500 C14 C15 1.358(4) C14 C16 1.419(4) C15 H15 0.9500 C16 C21 1.405(5) C16 C17 1.417(4) C17 C18 1.367(5) C18 C19 1.370(5) C18 H18 0.9500 C19 C20 1.388(5) C20 C21 1.361(5) C20 H20 0.9500 C21 H21 0.9500 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 H1E O4 0.86(5) 1.99(5) 2.765(4) 150(4) 2 yes N1 H1 O2 0.76(3) 2.66(4) 3.222(4) 133(3) 3_656 yes N3 H3 O1 0.84(3) 2.02(4) 2.826(4) 159(3) 1_556 yes