#------------------------------------------------------------------------------ #$Date: 2023-11-02 01:37:20 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287227 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247622.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_7247622 loop_ _publ_author_name 'Wood, Oskar G.' 'Jones, Leanne' 'Hawes, Chris Samuel' _publ_section_title ; Supporting coordination through hydrogen bonding in lanthanide complexes of 7-azaindole-N-oxide ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00985H _journal_year 2023 _chemical_formula_moiety '4(C7 H6 N2 O), 3(H2 O)' _chemical_formula_sum 'C28 H30 N8 O7' _chemical_formula_weight 590.60 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2023-08-02 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-08-10 deposited with the CCDC. 2023-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.0760(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.0792(8) _cell_length_b 7.8359(4) _cell_length_c 19.1930(9) _cell_measurement_reflns_used 9905 _cell_measurement_temperature 150.00 _cell_measurement_theta_max 30.457 _cell_measurement_theta_min 2.809 _cell_volume 2862.1(2) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 150.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 Quest ECO' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_unetI/netI 0.0396 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 59294 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.561 _diffrn_reflns_theta_min 2.809 _diffrn_source_current 20.0 _diffrn_source_power 1.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0621 before and 0.0570 after correction. The Ratio of minimum to maximum transmission is 0.9267. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.371 _exptl_crystal_description block _exptl_crystal_F_000 1240 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.275 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 418 _refine_ls_number_reflns 8783 _refine_ls_number_restraints 10 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0501 _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^)+(0.0417P)^2^+0.9836P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1005 _refine_ls_wR_factor_ref 0.1131 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6199 _reflns_number_total 8783 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00985h2.cif _cod_data_source_block L-H2O _cod_database_code 7247622 _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_max 0.988 _shelx_estimated_absorpt_t_min 0.961 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All N(H) groups, All O(H,H) groups 2. Restrained distances N3-H3 = N1-H1 = N5-H5A = N7-H7A 0.88 with sigma of 0.02 O7-H7B = O7-H7C = O6-H6B = O6-H6A = O5-H5B = O5-H5C 0.87 with sigma of 0.02 3.a Aromatic/amide H refined with riding coordinates: C1(H1A), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28) ; _shelx_res_file ; TITL ow_l1_mecn_0m_a.res in P2(1)/n ow_l1_mecn_0m.res created by SHELXL-2018/3 at 13:58:51 on 02-Aug-2023 REM Old TITL OW_L1_MeCN_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.120, Rweak 0.006, Alpha 0.022, Orientation as input REM Formula found by SHELXT: C28 N8 O7 CELL 0.71073 19.0792 7.8359 19.193 90 94.076 90 ZERR 4 0.0008 0.0004 0.0009 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 112 120 32 28 EQIV $1 1.5-X,-0.5+Y,0.5-Z EQIV $2 +X,-1+Y,+Z EQIV $3 +X,1+Y,+Z EQIV $4 0.5+X,0.5-Y,0.5+Z DFIX 0.88 N3 H3 N1 H1 N5 H5a N7 H7a DFIX 0.87 O7 H7b O7 H7c O6 H6b O6 H6a O5 H5b O5 H5c L.S. 4 PLAN 5 SIZE 0.12 0.24 0.4 TEMP -123.15 CONF HTAB N1 O2_$2 HTAB N3 O1_$3 HTAB N5 O4 HTAB N7 O3 HTAB O5 O2 HTAB O5 O6 HTAB O6 O3 HTAB O6 O5_$1 HTAB O7 O1_$4 HTAB O7 O4 BOND $H list 4 MORE -1 fmap 2 acta REM REM REM WGHT 0.041700 0.983600 FVAR 0.48385 O1 4 0.411808 0.041588 0.291487 11.00000 0.02799 0.02444 = 0.03179 0.00528 -0.00570 -0.00678 N1 3 0.550236 0.162695 0.293283 11.00000 0.02393 0.02247 = 0.02517 -0.00056 0.00177 -0.00017 H1 2 0.552349 0.052753 0.307823 11.00000 -1.50000 N2 3 0.425221 0.208178 0.285923 11.00000 0.02368 0.02607 = 0.02034 0.00089 -0.00301 -0.00213 C1 1 0.607505 0.270614 0.291608 11.00000 0.02378 0.03158 = 0.02812 -0.00514 0.00634 -0.00348 AFIX 43 H1A 2 0.655166 0.234741 0.296432 11.00000 -1.20000 AFIX 0 C2 1 0.586233 0.434601 0.282134 11.00000 0.03005 0.02772 = 0.03200 -0.00411 0.00674 -0.00695 AFIX 43 H2 2 0.615674 0.531470 0.278412 11.00000 -1.20000 AFIX 0 C3 1 0.511245 0.434224 0.278808 11.00000 0.03101 0.02393 = 0.02157 -0.00090 0.00295 -0.00164 C4 1 0.492500 0.261840 0.286282 11.00000 0.02382 0.02359 = 0.01824 -0.00101 0.00062 -0.00059 C5 1 0.457411 0.555287 0.271216 11.00000 0.03973 0.02378 = 0.02938 -0.00022 -0.00013 0.00177 AFIX 43 H5 2 0.467495 0.673046 0.265718 11.00000 -1.20000 AFIX 0 C6 1 0.389116 0.497716 0.271988 11.00000 0.03342 0.03209 = 0.03153 -0.00048 -0.00553 0.00868 AFIX 43 H6 2 0.351660 0.577684 0.267185 11.00000 -1.20000 AFIX 0 C7 1 0.373829 0.326117 0.279598 11.00000 0.02306 0.03643 = 0.02690 0.00049 -0.00544 0.00299 AFIX 43 H7 2 0.326226 0.291050 0.280366 11.00000 -1.20000 AFIX 0 O2 4 0.569673 0.834684 0.333531 11.00000 0.03177 0.02766 = 0.02777 0.00655 0.00777 0.00383 N3 3 0.453295 0.872419 0.413137 11.00000 0.02213 0.02429 = 0.02348 -0.00007 0.00066 -0.00033 H3 2 0.443490 0.926839 0.373406 11.00000 -1.50000 N4 3 0.571260 0.777007 0.399032 11.00000 0.02475 0.01932 = 0.02652 0.00080 0.00143 -0.00137 C8 1 0.409759 0.863353 0.467499 11.00000 0.02582 0.02983 = 0.03014 -0.00648 0.00592 -0.00413 AFIX 43 H8 2 0.363630 0.909403 0.466343 11.00000 -1.20000 AFIX 0 C9 1 0.441941 0.779603 0.522806 11.00000 0.03541 0.03090 = 0.02415 -0.00354 0.00574 -0.00690 AFIX 43 H9 2 0.422530 0.756004 0.566006 11.00000 -1.20000 AFIX 0 C10 1 0.510381 0.733682 0.503877 11.00000 0.03143 0.02065 = 0.02240 -0.00377 -0.00181 -0.00671 C11 1 0.513885 0.795122 0.435440 11.00000 0.02325 0.01791 = 0.02418 -0.00198 0.00023 -0.00320 C12 1 0.568921 0.649406 0.534861 11.00000 0.03980 0.02558 = 0.02649 0.00127 -0.00790 -0.00455 AFIX 43 H12 2 0.568616 0.604367 0.580793 11.00000 -1.20000 AFIX 0 C13 1 0.627388 0.633255 0.496862 11.00000 0.03221 0.02437 = 0.03961 0.00061 -0.01004 0.00034 AFIX 43 H13 2 0.667996 0.577374 0.517288 11.00000 -1.20000 AFIX 0 C14 1 0.628009 0.696836 0.429633 11.00000 0.02377 0.02494 = 0.03972 0.00094 -0.00088 0.00120 AFIX 43 H14 2 0.668938 0.683870 0.404687 11.00000 -1.20000 AFIX 0 O3 4 0.834208 0.645175 0.441448 11.00000 0.04037 0.02348 = 0.02943 0.00077 -0.00298 -0.00437 N5 3 0.905502 0.600178 0.572850 11.00000 0.02930 0.02288 = 0.02670 0.00048 0.00149 0.00046 H5A 2 0.863074 0.555025 0.574275 11.00000 -1.50000 N6 3 0.900583 0.697005 0.453724 11.00000 0.03651 0.01708 = 0.02843 -0.00218 0.00409 0.00110 C15 1 0.956595 0.604825 0.627402 11.00000 0.03628 0.02932 = 0.03002 0.00161 -0.00187 0.00310 AFIX 43 H15 2 0.951265 0.560735 0.672830 11.00000 -1.20000 AFIX 0 C16 1 1.015585 0.681365 0.606948 11.00000 0.03050 0.03427 = 0.04018 0.00113 -0.00267 0.00204 AFIX 43 H16 2 1.057856 0.700386 0.635091 11.00000 -1.20000 AFIX 0 C17 1 1.002367 0.727834 0.535524 11.00000 0.02891 0.02293 = 0.03944 -0.00203 0.00642 0.00551 C18 1 0.933139 0.673873 0.517579 11.00000 0.03294 0.01598 = 0.02839 -0.00194 0.00593 0.00328 C19 1 1.038253 0.810075 0.484250 11.00000 0.03079 0.02895 = 0.05161 -0.00016 0.01340 0.00196 AFIX 43 H19 2 1.084876 0.850416 0.493988 11.00000 -1.20000 AFIX 0 C20 1 1.004119 0.831081 0.419097 11.00000 0.04624 0.02837 = 0.04270 0.00169 0.02081 0.00236 AFIX 43 H20 2 1.028018 0.885440 0.383425 11.00000 -1.20000 AFIX 0 C21 1 0.936093 0.775138 0.404372 11.00000 0.05132 0.02474 = 0.02867 0.00071 0.01071 0.00355 AFIX 43 H21 2 0.913987 0.791813 0.358956 11.00000 -1.20000 AFIX 0 O4 4 0.775449 0.452514 0.587882 11.00000 0.03333 0.02411 = 0.02417 -0.00583 0.00178 -0.00133 N7 3 0.788834 0.315112 0.455060 11.00000 0.03100 0.01903 = 0.01970 -0.00040 0.00235 -0.00123 H7A 2 0.801718 0.425294 0.454045 11.00000 -1.50000 N8 3 0.772329 0.283982 0.577444 11.00000 0.02092 0.02433 = 0.02015 -0.00150 0.00005 -0.00205 C22 1 0.792264 0.200806 0.400547 11.00000 0.03381 0.02731 = 0.01951 -0.00429 0.00332 -0.00145 AFIX 43 H22 2 0.799619 0.231596 0.353751 11.00000 -1.20000 AFIX 0 C23 1 0.783660 0.038278 0.423156 11.00000 0.03233 0.02291 = 0.02629 -0.00569 0.00315 -0.00046 AFIX 43 H23 2 0.783289 -0.062179 0.395422 11.00000 -1.20000 AFIX 0 C24 1 0.775272 0.046855 0.496502 11.00000 0.01994 0.02209 = 0.02619 0.00025 0.00096 -0.00047 C25 1 0.778616 0.222092 0.512569 11.00000 0.01879 0.02259 = 0.01930 0.00081 0.00108 0.00036 C26 1 0.767609 -0.068584 0.550672 11.00000 0.02533 0.02368 = 0.03405 0.00562 0.00066 -0.00271 AFIX 43 H26 2 0.766888 -0.188191 0.542564 11.00000 -1.20000 AFIX 0 C27 1 0.761105 -0.002429 0.616583 11.00000 0.02904 0.03494 = 0.02917 0.01132 -0.00015 -0.00453 AFIX 43 H27 2 0.755470 -0.078328 0.654376 11.00000 -1.20000 AFIX 0 C28 1 0.762582 0.171828 0.629049 11.00000 0.02606 0.03767 = 0.01948 0.00340 0.00071 -0.00382 AFIX 43 H28 2 0.756612 0.212889 0.674821 11.00000 -1.20000 AFIX 0 O5 4 0.683366 0.854597 0.256529 11.00000 0.04468 0.04394 = 0.03617 0.01515 0.01867 0.01406 H5B 2 0.714948 0.779981 0.273804 11.00000 -1.50000 H5C 2 0.647762 0.852689 0.282973 11.00000 -1.50000 O6 4 0.765673 0.614080 0.315025 11.00000 0.03933 0.03957 = 0.03382 -0.00175 -0.00235 0.01073 H6A 2 0.782579 0.534294 0.289299 11.00000 -1.50000 H6B 2 0.792870 0.625719 0.353302 11.00000 -1.50000 O7 4 0.789732 0.595878 0.722020 11.00000 0.03268 0.04475 = 0.02414 -0.00850 -0.00256 0.01567 H7B 2 0.785570 0.549348 0.680714 11.00000 -1.50000 H7C 2 0.827531 0.552930 0.743493 11.00000 -1.50000 HKLF 4 REM ow_l1_mecn_0m_a.res in P2(1)/n REM wR2 = 0.113132, GooF = S = 1.04230, Restrained GooF = 1.04188 for all data REM R1 = 0.050118 for 6199 Fo > 4sig(Fo) and 0.082134 for all 8783 data REM 418 parameters refined using 10 restraints END WGHT 0.0417 0.9837 REM Highest difference peak 0.275, deepest hole -0.255, 1-sigma level 0.047 Q1 1 0.7785 0.0389 0.4593 11.00000 0.05 0.28 Q2 1 0.5164 0.7596 0.4694 11.00000 0.05 0.25 Q3 1 0.7765 -0.0175 0.5188 11.00000 0.05 0.22 Q4 1 0.7813 0.1219 0.4120 11.00000 0.05 0.22 Q5 1 0.5377 0.7062 0.5221 11.00000 0.05 0.22 ; _shelx_res_checksum 36955 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.41181(5) 0.04159(13) 0.29149(5) 0.0284(2) Uani 1 1 d . . . . . N1 N 0.55024(6) 0.16269(15) 0.29328(6) 0.0239(2) Uani 1 1 d D . . . . H1 H 0.5523(9) 0.0528(19) 0.3078(9) 0.036 Uiso 1 1 d D U . . . N2 N 0.42522(6) 0.20818(15) 0.28592(6) 0.0236(2) Uani 1 1 d . . . . . C1 C 0.60751(8) 0.27061(19) 0.29161(7) 0.0276(3) Uani 1 1 d . . . . . H1A H 0.655166 0.234741 0.296432 0.033 Uiso 1 1 calc R U . . . C2 C 0.58623(8) 0.43460(19) 0.28213(8) 0.0297(3) Uani 1 1 d . . . . . H2 H 0.615674 0.531470 0.278412 0.036 Uiso 1 1 calc R U . . . C3 C 0.51125(8) 0.43422(18) 0.27881(7) 0.0254(3) Uani 1 1 d . . . . . C4 C 0.49250(7) 0.26184(17) 0.28628(7) 0.0219(3) Uani 1 1 d . . . . . C5 C 0.45741(8) 0.55529(19) 0.27122(8) 0.0311(3) Uani 1 1 d . . . . . H5 H 0.467495 0.673046 0.265718 0.037 Uiso 1 1 calc R U . . . C6 C 0.38912(8) 0.4977(2) 0.27199(8) 0.0327(3) Uani 1 1 d . . . . . H6 H 0.351660 0.577684 0.267185 0.039 Uiso 1 1 calc R U . . . C7 C 0.37383(8) 0.3261(2) 0.27960(8) 0.0291(3) Uani 1 1 d . . . . . H7 H 0.326226 0.291050 0.280366 0.035 Uiso 1 1 calc R U . . . O2 O 0.56967(5) 0.83468(13) 0.33353(5) 0.0288(2) Uani 1 1 d . . . . . N3 N 0.45329(6) 0.87242(15) 0.41314(6) 0.0233(2) Uani 1 1 d D . . . . H3 H 0.4435(9) 0.927(2) 0.3734(8) 0.035 Uiso 1 1 d D U . . . N4 N 0.57126(6) 0.77701(14) 0.39903(6) 0.0236(2) Uani 1 1 d . . . . . C8 C 0.40976(8) 0.86335(19) 0.46750(8) 0.0284(3) Uani 1 1 d . . . . . H8 H 0.363630 0.909403 0.466343 0.034 Uiso 1 1 calc R U . . . C9 C 0.44194(8) 0.77960(19) 0.52281(8) 0.0300(3) Uani 1 1 d . . . . . H9 H 0.422530 0.756004 0.566006 0.036 Uiso 1 1 calc R U . . . C10 C 0.51038(7) 0.73368(17) 0.50388(7) 0.0250(3) Uani 1 1 d . . . . . C11 C 0.51388(7) 0.79512(16) 0.43544(7) 0.0218(3) Uani 1 1 d . . . . . C12 C 0.56892(8) 0.64941(19) 0.53486(8) 0.0311(3) Uani 1 1 d . . . . . H12 H 0.568616 0.604367 0.580793 0.037 Uiso 1 1 calc R U . . . C13 C 0.62739(8) 0.63326(19) 0.49686(8) 0.0327(3) Uani 1 1 d . . . . . H13 H 0.667996 0.577374 0.517288 0.039 Uiso 1 1 calc R U . . . C14 C 0.62801(8) 0.69684(18) 0.42963(8) 0.0296(3) Uani 1 1 d . . . . . H14 H 0.668938 0.683870 0.404687 0.036 Uiso 1 1 calc R U . . . O3 O 0.83421(6) 0.64517(13) 0.44145(5) 0.0314(2) Uani 1 1 d . . . . . N5 N 0.90550(7) 0.60018(15) 0.57285(6) 0.0263(3) Uani 1 1 d D . . . . H5A H 0.8631(8) 0.555(2) 0.5743(9) 0.039 Uiso 1 1 d D U . . . N6 N 0.90058(7) 0.69700(14) 0.45372(6) 0.0273(3) Uani 1 1 d . . . . . C15 C 0.95660(8) 0.6048(2) 0.62740(8) 0.0321(3) Uani 1 1 d . . . . . H15 H 0.951265 0.560735 0.672830 0.038 Uiso 1 1 calc R U . . . C16 C 1.01558(8) 0.6814(2) 0.60695(9) 0.0352(3) Uani 1 1 d . . . . . H16 H 1.057856 0.700386 0.635091 0.042 Uiso 1 1 calc R U . . . C17 C 1.00237(8) 0.72783(18) 0.53552(8) 0.0302(3) Uani 1 1 d . . . . . C18 C 0.93314(8) 0.67387(17) 0.51758(7) 0.0256(3) Uani 1 1 d . . . . . C19 C 1.03825(9) 0.8101(2) 0.48425(9) 0.0366(4) Uani 1 1 d . . . . . H19 H 1.084876 0.850416 0.493988 0.044 Uiso 1 1 calc R U . . . C20 C 1.00412(9) 0.8311(2) 0.41910(9) 0.0383(4) Uani 1 1 d . . . . . H20 H 1.028018 0.885440 0.383425 0.046 Uiso 1 1 calc R U . . . C21 C 0.93609(9) 0.77514(19) 0.40437(8) 0.0345(3) Uani 1 1 d . . . . . H21 H 0.913987 0.791813 0.358956 0.041 Uiso 1 1 calc R U . . . O4 O 0.77545(5) 0.45251(13) 0.58788(5) 0.0272(2) Uani 1 1 d . . . . . N7 N 0.78883(6) 0.31511(14) 0.45506(6) 0.0232(2) Uani 1 1 d D . . . . H7A H 0.8017(9) 0.4253(18) 0.4540(9) 0.035 Uiso 1 1 d D U . . . N8 N 0.77233(6) 0.28398(15) 0.57744(6) 0.0219(2) Uani 1 1 d . . . . . C22 C 0.79226(8) 0.20081(18) 0.40055(7) 0.0268(3) Uani 1 1 d . . . . . H22 H 0.799619 0.231596 0.353751 0.032 Uiso 1 1 calc R U . . . C23 C 0.78366(8) 0.03828(18) 0.42316(7) 0.0271(3) Uani 1 1 d . . . . . H23 H 0.783289 -0.062179 0.395422 0.033 Uiso 1 1 calc R U . . . C24 C 0.77527(7) 0.04685(17) 0.49650(7) 0.0228(3) Uani 1 1 d . . . . . C25 C 0.77862(7) 0.22209(17) 0.51257(7) 0.0202(2) Uani 1 1 d . . . . . C26 C 0.76761(7) -0.06858(19) 0.55067(8) 0.0278(3) Uani 1 1 d . . . . . H26 H 0.766888 -0.188191 0.542564 0.033 Uiso 1 1 calc R U . . . C27 C 0.76111(8) -0.0024(2) 0.61658(8) 0.0312(3) Uani 1 1 d . . . . . H27 H 0.755470 -0.078328 0.654376 0.037 Uiso 1 1 calc R U . . . C28 C 0.76258(7) 0.1718(2) 0.62905(7) 0.0278(3) Uani 1 1 d . . . . . H28 H 0.756612 0.212889 0.674821 0.033 Uiso 1 1 calc R U . . . O5 O 0.68337(7) 0.85460(16) 0.25653(6) 0.0408(3) Uani 1 1 d D . . . . H5B H 0.7149(10) 0.780(3) 0.2738(11) 0.061 Uiso 1 1 d D U . . . H5C H 0.6478(10) 0.853(3) 0.2830(11) 0.061 Uiso 1 1 d D U . . . O6 O 0.76567(6) 0.61408(16) 0.31502(6) 0.0378(3) Uani 1 1 d D . . . . H6A H 0.7826(10) 0.534(2) 0.2893(10) 0.057 Uiso 1 1 d D U . . . H6B H 0.7929(10) 0.626(3) 0.3533(9) 0.057 Uiso 1 1 d D U . . . O7 O 0.78973(6) 0.59588(15) 0.72202(6) 0.0341(3) Uani 1 1 d D . . . . H7B H 0.7856(10) 0.549(3) 0.6807(8) 0.051 Uiso 1 1 d D U . . . H7C H 0.8275(9) 0.553(3) 0.7435(10) 0.051 Uiso 1 1 d D 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 0.0280(5) 0.0244(5) 0.0318(5) 0.0053(4) -0.0057(4) -0.0068(4) N1 0.0239(6) 0.0225(5) 0.0252(6) -0.0006(5) 0.0018(5) -0.0002(4) N2 0.0237(6) 0.0261(6) 0.0203(5) 0.0009(4) -0.0030(4) -0.0021(4) C1 0.0238(7) 0.0316(7) 0.0281(7) -0.0051(6) 0.0063(5) -0.0035(6) C2 0.0301(8) 0.0277(7) 0.0320(7) -0.0041(6) 0.0067(6) -0.0070(6) C3 0.0310(7) 0.0239(6) 0.0216(6) -0.0009(5) 0.0029(5) -0.0016(5) C4 0.0238(6) 0.0236(6) 0.0182(6) -0.0010(5) 0.0006(5) -0.0006(5) C5 0.0397(9) 0.0238(7) 0.0294(7) -0.0002(6) -0.0001(6) 0.0018(6) C6 0.0334(8) 0.0321(8) 0.0315(8) -0.0005(6) -0.0055(6) 0.0087(6) C7 0.0231(7) 0.0364(8) 0.0269(7) 0.0005(6) -0.0054(5) 0.0030(6) O2 0.0318(5) 0.0277(5) 0.0278(5) 0.0065(4) 0.0078(4) 0.0038(4) N3 0.0221(6) 0.0243(6) 0.0235(6) -0.0001(4) 0.0007(4) -0.0003(4) N4 0.0248(6) 0.0193(5) 0.0265(6) 0.0008(4) 0.0014(4) -0.0014(4) C8 0.0258(7) 0.0298(7) 0.0301(7) -0.0065(6) 0.0059(6) -0.0041(6) C9 0.0354(8) 0.0309(7) 0.0242(7) -0.0035(6) 0.0057(6) -0.0069(6) C10 0.0314(7) 0.0207(6) 0.0224(6) -0.0038(5) -0.0018(5) -0.0067(5) C11 0.0232(6) 0.0179(6) 0.0242(6) -0.0020(5) 0.0002(5) -0.0032(5) C12 0.0398(9) 0.0256(7) 0.0265(7) 0.0013(6) -0.0079(6) -0.0045(6) C13 0.0322(8) 0.0244(7) 0.0396(8) 0.0006(6) -0.0100(6) 0.0003(6) C14 0.0238(7) 0.0249(7) 0.0397(8) 0.0009(6) -0.0009(6) 0.0012(5) O3 0.0404(6) 0.0235(5) 0.0294(5) 0.0008(4) -0.0030(4) -0.0044(4) N5 0.0293(6) 0.0229(6) 0.0267(6) 0.0005(5) 0.0015(5) 0.0005(5) N6 0.0365(7) 0.0171(5) 0.0284(6) -0.0022(4) 0.0041(5) 0.0011(5) C15 0.0363(8) 0.0293(7) 0.0300(7) 0.0016(6) -0.0019(6) 0.0031(6) C16 0.0305(8) 0.0343(8) 0.0402(9) 0.0011(7) -0.0027(7) 0.0020(6) C17 0.0289(7) 0.0229(7) 0.0394(8) -0.0020(6) 0.0064(6) 0.0055(6) C18 0.0329(7) 0.0160(6) 0.0284(7) -0.0019(5) 0.0059(6) 0.0033(5) C19 0.0308(8) 0.0289(8) 0.0516(10) -0.0002(7) 0.0134(7) 0.0020(6) C20 0.0462(10) 0.0284(8) 0.0427(9) 0.0017(7) 0.0208(8) 0.0024(7) C21 0.0513(10) 0.0247(7) 0.0287(7) 0.0007(6) 0.0107(7) 0.0035(7) O4 0.0333(6) 0.0241(5) 0.0242(5) -0.0058(4) 0.0018(4) -0.0013(4) N7 0.0310(6) 0.0190(5) 0.0197(5) -0.0004(4) 0.0024(4) -0.0012(5) N8 0.0209(5) 0.0243(6) 0.0202(5) -0.0015(4) 0.0000(4) -0.0021(4) C22 0.0338(8) 0.0273(7) 0.0195(6) -0.0043(5) 0.0033(5) -0.0015(6) C23 0.0323(8) 0.0229(6) 0.0263(7) -0.0057(5) 0.0032(6) -0.0005(6) C24 0.0199(6) 0.0221(6) 0.0262(7) 0.0002(5) 0.0010(5) -0.0005(5) C25 0.0188(6) 0.0226(6) 0.0193(6) 0.0008(5) 0.0011(5) 0.0004(5) C26 0.0253(7) 0.0237(7) 0.0341(8) 0.0056(6) 0.0007(6) -0.0027(5) C27 0.0290(8) 0.0349(8) 0.0292(7) 0.0113(6) -0.0002(6) -0.0045(6) C28 0.0261(7) 0.0377(8) 0.0195(6) 0.0034(6) 0.0007(5) -0.0038(6) O5 0.0447(7) 0.0439(7) 0.0362(6) 0.0151(5) 0.0187(5) 0.0141(5) O6 0.0393(7) 0.0396(6) 0.0338(6) -0.0018(5) -0.0024(5) 0.0107(5) O7 0.0327(6) 0.0448(7) 0.0241(5) -0.0085(5) -0.0026(4) 0.0157(5) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1 124.8(11) . . ? C4 N1 H1 126.7(11) . . ? C4 N1 C1 106.66(12) . . ? O1 N2 C4 119.43(11) . . ? O1 N2 C7 122.37(12) . . ? C7 N2 C4 118.20(12) . . ? N1 C1 H1A 124.7 . . ? C2 C1 N1 110.67(13) . . ? C2 C1 H1A 124.7 . . ? C1 C2 H2 126.5 . . ? C1 C2 C3 107.07(13) . . ? C3 C2 H2 126.5 . . ? C4 C3 C2 104.99(12) . . ? C5 C3 C2 136.86(14) . . ? C5 C3 C4 118.15(13) . . ? N1 C4 N2 126.25(12) . . ? N1 C4 C3 110.60(12) . . ? N2 C4 C3 123.15(12) . . ? C3 C5 H5 121.2 . . ? C6 C5 C3 117.66(14) . . ? C6 C5 H5 121.2 . . ? C5 C6 H6 119.2 . . ? C5 C6 C7 121.62(14) . . ? C7 C6 H6 119.2 . . ? N2 C7 C6 121.20(14) . . ? N2 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C8 N3 H3 125.2(11) . . ? C11 N3 H3 128.0(11) . . ? C11 N3 C8 106.58(12) . . ? O2 N4 C11 119.22(11) . . ? O2 N4 C14 122.11(12) . . ? C11 N4 C14 118.66(12) . . ? N3 C8 H8 124.7 . . ? C9 C8 N3 110.66(13) . . ? C9 C8 H8 124.7 . . ? C8 C9 H9 126.4 . . ? C8 C9 C10 107.11(13) . . ? C10 C9 H9 126.4 . . ? C11 C10 C9 104.89(12) . . ? C12 C10 C9 136.99(14) . . ? C12 C10 C11 118.12(13) . . ? N3 C11 C10 110.75(12) . . ? N4 C11 N3 126.36(12) . . ? N4 C11 C10 122.90(12) . . ? C10 C12 H12 121.0 . . ? C13 C12 C10 118.09(14) . . ? C13 C12 H12 121.0 . . ? C12 C13 H13 119.3 . . ? C12 C13 C14 121.33(14) . . ? C14 C13 H13 119.3 . . ? N4 C14 C13 120.90(14) . . ? N4 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C15 N5 H5A 125.8(12) . . ? C18 N5 H5A 127.2(12) . . ? C18 N5 C15 106.93(13) . . ? O3 N6 C18 119.36(12) . . ? O3 N6 C21 122.09(13) . . ? C18 N6 C21 118.54(13) . . ? N5 C15 H15 124.8 . . ? C16 C15 N5 110.35(14) . . ? C16 C15 H15 124.8 . . ? C15 C16 H16 126.3 . . ? C15 C16 C17 107.32(14) . . ? C17 C16 H16 126.3 . . ? C18 C17 C16 104.95(13) . . ? C19 C17 C16 137.30(15) . . ? C19 C17 C18 117.74(15) . . ? N5 C18 C17 110.44(13) . . ? N6 C18 N5 126.39(13) . . ? N6 C18 C17 123.17(13) . . ? C17 C19 H19 120.9 . . ? C20 C19 C17 118.10(15) . . ? C20 C19 H19 120.9 . . ? C19 C20 H20 119.2 . . ? C19 C20 C21 121.66(15) . . ? C21 C20 H20 119.2 . . ? N6 C21 C20 120.80(15) . . ? N6 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C22 N7 H7A 125.4(11) . . ? C25 N7 H7A 126.4(11) . . ? C25 N7 C22 106.66(11) . . ? O4 N8 C25 119.17(11) . . ? O4 N8 C28 122.79(11) . . ? C28 N8 C25 118.03(12) . . ? N7 C22 H22 124.7 . . ? C23 C22 N7 110.62(12) . . ? C23 C22 H22 124.7 . . ? C22 C23 H23 126.4 . . ? C22 C23 C24 107.15(12) . . ? C24 C23 H23 126.4 . . ? C25 C24 C23 104.78(12) . . ? C26 C24 C23 136.81(13) . . ? C26 C24 C25 118.37(13) . . ? N7 C25 N8 126.05(12) . . ? N7 C25 C24 110.79(11) . . ? N8 C25 C24 123.16(12) . . ? C24 C26 H26 121.3 . . ? C27 C26 C24 117.44(14) . . ? C27 C26 H26 121.3 . . ? C26 C27 H27 119.1 . . ? C26 C27 C28 121.73(13) . . ? C28 C27 H27 119.1 . . ? N8 C28 C27 121.20(13) . . ? N8 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? H5B O5 H5C 108(2) . . ? H6A O6 H6B 109.2(19) . . ? H7B O7 H7C 106.7(18) . . ? 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 N2 1.3360(15) . ? N1 H1 0.906(14) . ? N1 C1 1.3838(18) . ? N1 C4 1.3469(17) . ? N2 C4 1.3503(17) . ? N2 C7 1.3466(18) . ? C1 H1A 0.9500 . ? C1 C2 1.356(2) . ? C2 H2 0.9500 . ? C2 C3 1.428(2) . ? C3 C4 1.4073(19) . ? C3 C5 1.398(2) . ? C5 H5 0.9500 . ? C5 C6 1.380(2) . ? C6 H6 0.9500 . ? C6 C7 1.386(2) . ? C7 H7 0.9500 . ? O2 N4 1.3342(15) . ? N3 H3 0.882(13) . ? N3 C8 1.3809(18) . ? N3 C11 1.3476(17) . ? N4 C11 1.3474(17) . ? N4 C14 1.3496(18) . ? C8 H8 0.9500 . ? C8 C9 1.357(2) . ? C9 H9 0.9500 . ? C9 C10 1.426(2) . ? C10 C11 1.4050(19) . ? C10 C12 1.394(2) . ? C12 H12 0.9500 . ? C12 C13 1.381(2) . ? C13 H13 0.9500 . ? C13 C14 1.384(2) . ? C14 H14 0.9500 . ? O3 N6 1.3348(16) . ? N5 H5A 0.886(14) . ? N5 C15 1.3794(19) . ? N5 C18 1.3477(18) . ? N6 C18 1.3463(19) . ? N6 C21 1.3499(19) . ? C15 H15 0.9500 . ? C15 C16 1.358(2) . ? C16 H16 0.9500 . ? C16 C17 1.423(2) . ? C17 C18 1.406(2) . ? C17 C19 1.396(2) . ? C19 H19 0.9500 . ? C19 C20 1.378(3) . ? C20 H20 0.9500 . ? C20 C21 1.380(2) . ? C21 H21 0.9500 . ? O4 N8 1.3364(15) . ? N7 H7A 0.898(14) . ? N7 C22 1.3824(17) . ? N7 C25 1.3484(17) . ? N8 C25 1.3495(17) . ? N8 C28 1.3469(18) . ? C22 H22 0.9500 . ? C22 C23 1.359(2) . ? C23 H23 0.9500 . ? C23 C24 1.4296(19) . ? C24 C25 1.4078(18) . ? C24 C26 1.3936(19) . ? C26 H26 0.9500 . ? C26 C27 1.381(2) . ? C27 H27 0.9500 . ? C27 C28 1.386(2) . ? C28 H28 0.9500 . ? O5 H5B 0.887(15) . ? O5 H5C 0.877(16) . ? O6 H6A 0.873(15) . ? O6 H6B 0.874(15) . ? O7 H7B 0.871(15) . ? O7 H7C 0.872(15) . ? 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 N1 H1 O2 0.906(14) 1.803(14) 2.7018(15) 171.7(16) 1_545 yes N3 H3 O1 0.882(13) 1.874(14) 2.7518(15) 173.4(16) 1_565 yes N5 H5A O4 0.886(14) 1.890(14) 2.7714(16) 173.6(17) . yes N7 H7A O3 0.898(14) 1.853(14) 2.7457(15) 172.4(16) . yes O5 H5B O6 0.887(15) 1.773(16) 2.6510(16) 170(2) . yes O5 H5C O2 0.877(16) 1.840(16) 2.7147(15) 175(2) . yes O6 H6A O5 0.873(15) 1.805(16) 2.6750(17) 174(2) 2_645 yes O6 H6B O3 0.874(15) 1.821(16) 2.6843(16) 169(2) . yes O7 H7B O4 0.871(15) 1.934(15) 2.8044(14) 178(2) . yes O7 H7C O1 0.872(15) 1.942(15) 2.8145(14) 180(2) 4_666 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 O1 N2 C4 N1 -1.46(19) . . . . ? O1 N2 C4 C3 178.25(12) . . . . ? O1 N2 C7 C6 -178.21(13) . . . . ? N1 C1 C2 C3 1.16(17) . . . . ? C1 N1 C4 N2 -179.27(13) . . . . ? C1 N1 C4 C3 0.99(15) . . . . ? C1 C2 C3 C4 -0.52(16) . . . . ? C1 C2 C3 C5 178.74(16) . . . . ? C2 C3 C4 N1 -0.31(15) . . . . ? C2 C3 C4 N2 179.95(12) . . . . ? C2 C3 C5 C6 -178.80(16) . . . . ? C3 C5 C6 C7 -0.4(2) . . . . ? C4 N1 C1 C2 -1.35(16) . . . . ? C4 N2 C7 C6 1.5(2) . . . . ? C4 C3 C5 C6 0.4(2) . . . . ? C5 C3 C4 N1 -179.73(12) . . . . ? C5 C3 C4 N2 0.5(2) . . . . ? C5 C6 C7 N2 -0.6(2) . . . . ? C7 N2 C4 N1 178.83(13) . . . . ? C7 N2 C4 C3 -1.47(19) . . . . ? O2 N4 C11 N3 -2.2(2) . . . . ? O2 N4 C11 C10 178.10(12) . . . . ? O2 N4 C14 C13 -177.83(13) . . . . ? N3 C8 C9 C10 0.81(17) . . . . ? C8 N3 C11 N4 -179.18(13) . . . . ? C8 N3 C11 C10 0.57(15) . . . . ? C8 C9 C10 C11 -0.44(15) . . . . ? C8 C9 C10 C12 179.73(16) . . . . ? C9 C10 C11 N3 -0.09(15) . . . . ? C9 C10 C11 N4 179.67(12) . . . . ? C9 C10 C12 C13 -179.28(15) . . . . ? C10 C12 C13 C14 -0.7(2) . . . . ? C11 N3 C8 C9 -0.87(16) . . . . ? C11 N4 C14 C13 0.4(2) . . . . ? C11 C10 C12 C13 0.9(2) . . . . ? C12 C10 C11 N3 179.78(12) . . . . ? C12 C10 C11 N4 -0.5(2) . . . . ? C12 C13 C14 N4 0.0(2) . . . . ? C14 N4 C11 N3 179.50(13) . . . . ? C14 N4 C11 C10 -0.22(19) . . . . ? O3 N6 C18 N5 0.5(2) . . . . ? O3 N6 C18 C17 -178.56(12) . . . . ? O3 N6 C21 C20 178.40(13) . . . . ? N5 C15 C16 C17 -0.36(18) . . . . ? C15 N5 C18 N6 -179.39(13) . . . . ? C15 N5 C18 C17 -0.20(16) . . . . ? C15 C16 C17 C18 0.22(17) . . . . ? C15 C16 C17 C19 178.66(17) . . . . ? C16 C17 C18 N5 -0.01(16) . . . . ? C16 C17 C18 N6 179.21(13) . . . . ? C16 C17 C19 C20 -179.22(17) . . . . ? C17 C19 C20 C21 0.8(2) . . . . ? C18 N5 C15 C16 0.35(17) . . . . ? C18 N6 C21 C20 -0.4(2) . . . . ? C18 C17 C19 C20 -0.9(2) . . . . ? C19 C17 C18 N5 -178.81(13) . . . . ? C19 C17 C18 N6 0.4(2) . . . . ? C19 C20 C21 N6 -0.2(2) . . . . ? C21 N6 C18 N5 179.35(13) . . . . ? C21 N6 C18 C17 0.3(2) . . . . ? O4 N8 C25 N7 0.78(19) . . . . ? O4 N8 C25 C24 -179.33(12) . . . . ? O4 N8 C28 C27 -178.62(13) . . . . ? N7 C22 C23 C24 -0.93(17) . . . . ? C22 N7 C25 N8 179.92(13) . . . . ? C22 N7 C25 C24 0.01(15) . . . . ? C22 C23 C24 C25 0.89(16) . . . . ? C22 C23 C24 C26 -176.67(16) . . . . ? C23 C24 C25 N7 -0.56(15) . . . . ? C23 C24 C25 N8 179.53(12) . . . . ? C23 C24 C26 C27 179.71(15) . . . . ? C24 C26 C27 C28 -0.5(2) . . . . ? C25 N7 C22 C23 0.58(16) . . . . ? C25 N8 C28 C27 1.9(2) . . . . ? C25 C24 C26 C27 2.4(2) . . . . ? C26 C24 C25 N7 177.54(12) . . . . ? C26 C24 C25 N8 -2.4(2) . . . . ? C26 C27 C28 N8 -1.8(2) . . . . ? C28 N8 C25 N7 -179.71(13) . . . . ? C28 N8 C25 C24 0.18(19) . . . . ?