#------------------------------------------------------------------------------ #$Date: 2023-11-02 01:37:20 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287227 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247627.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_7247627 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 'C21 H18 Gd N9 O12' _chemical_formula_sum 'C21 H18 Gd N9 O12' _chemical_formula_weight 745.69 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 78.6810(10) _cell_angle_beta 77.1570(10) _cell_angle_gamma 70.8240(10) _cell_formula_units_Z 2 _cell_length_a 8.5744(3) _cell_length_b 11.7399(4) _cell_length_c 14.2153(5) _cell_measurement_reflns_used 9973 _cell_measurement_temperature 150.00 _cell_measurement_theta_max 28.706 _cell_measurement_theta_min 2.524 _cell_volume 1305.88(8) _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 0.997 _diffrn_measured_fraction_theta_max 0.994 _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 0.0228 _diffrn_reflns_av_unetI/netI 0.0200 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 27414 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.705 _diffrn_reflns_theta_min 3.163 _diffrn_source_current 20.0 _diffrn_source_power 1.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.622 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.6210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0559 before and 0.0371 after correction. The Ratio of minimum to maximum transmission is 0.8327. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.896 _exptl_crystal_description block _exptl_crystal_F_000 734 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.449 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.068 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 397 _refine_ls_number_reflns 6724 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.114 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0174 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0089P)^2^+1.0644P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0384 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6411 _reflns_number_total 6724 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00985h2.cif _cod_data_source_block 3 _cod_database_code 7247627 _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 0.622 _shelx_estimated_absorpt_t_min 0.560 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 2. Restrained distances N2-H2 = N4-H4 = N6-H6 0.88 with sigma of 0.02 3.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2A), C3(H3), C6(H6A), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21) ; _shelx_res_file ; TITL ow5ay_et2o_0m_a.res in P-1 ow5ay_et2o_0m.res created by SHELXL-2018/3 at 14:58:11 on 02-Aug-2023 REM Old TITL OW5AY_Et2O_0m in P-1 REM SHELXT solution in P-1 REM R1 0.051, Rweak 0.011, Alpha 0.063, Orientation as input REM Formula found by SHELXT: C26 N7 O9 Gd CELL 0.71073 8.5744 11.7399 14.2153 78.681 77.157 70.824 ZERR 2 0.0003 0.0004 0.0005 0.001 0.001 0.001 LATT 1 SFAC C H Gd N O UNIT 42 36 2 18 24 DFIX 0.88 N2 H2 N4 H4 N6 H6 L.S. 4 PLAN 5 SIZE 0.2 0.21 0.25 TEMP -123.15 CONF HTAB N2 O2 HTAB N4 O3 HTAB N6 O1 CONN 12 1.5 $Gd BOND $H list 4 MORE -1 fmap 2 acta OMIT 1 1 2 OMIT 0 -3 1 OMIT 1 0 0 OMIT 0 0 2 REM REM REM WGHT 0.008900 1.064400 FVAR 0.46473 GD1 3 0.478776 0.697617 0.712799 11.00000 0.01645 0.01309 = 0.01425 -0.00221 -0.00178 -0.00454 O1 5 0.687873 0.638544 0.810021 11.00000 0.02377 0.01851 = 0.02183 -0.00357 -0.00787 -0.00852 O2 5 0.705366 0.731946 0.599607 11.00000 0.02453 0.02148 = 0.01414 -0.00405 0.00295 -0.00993 O3 5 0.621388 0.500975 0.676554 11.00000 0.02716 0.01268 = 0.01865 0.00005 -0.00134 -0.00618 O4 5 0.299291 0.821459 0.838073 11.00000 0.02822 0.02192 = 0.02337 -0.00712 0.00036 -0.01103 O5 5 0.481077 0.901459 0.743803 11.00000 0.02203 0.02197 = 0.03000 -0.00779 0.00176 -0.00825 O6 5 0.295422 1.003351 0.852573 11.00000 0.04541 0.02269 = 0.03144 -0.01480 -0.00025 -0.00757 O7 5 0.305298 0.861484 0.609840 11.00000 0.03222 0.01899 = 0.02409 -0.00163 -0.00603 -0.00453 O8 5 0.402081 0.689341 0.554107 11.00000 0.02831 0.02280 = 0.02037 -0.00438 -0.00544 -0.00355 O9 5 0.203794 0.833782 0.491631 11.00000 0.04318 0.05442 = 0.03249 -0.00648 -0.02219 0.00594 O10 5 0.212327 0.651870 0.746161 11.00000 0.02594 0.02274 = 0.01913 0.00192 -0.00671 -0.01114 O11 5 0.370823 0.562448 0.854071 11.00000 0.02112 0.02250 = 0.02147 0.00083 -0.00439 -0.00537 O12 5 0.116580 0.550357 0.878982 11.00000 0.02546 0.03631 = 0.03241 0.00694 0.00153 -0.01535 N1 4 0.734655 0.699625 0.864109 11.00000 0.01791 0.01921 = 0.02154 -0.00491 -0.00470 -0.00521 N2 4 0.844366 0.818050 0.723250 11.00000 0.02019 0.02422 = 0.02078 -0.00411 -0.00260 -0.00895 H2 2 0.816164 0.792066 0.678375 11.00000 -1.20000 N3 4 0.763177 0.744443 0.503846 11.00000 0.01800 0.01732 = 0.01600 -0.00241 -0.00097 -0.00592 N4 4 0.802433 0.534907 0.491477 11.00000 0.02209 0.01630 = 0.01857 -0.00358 -0.00016 -0.00744 H4 2 0.754618 0.513229 0.549492 11.00000 -1.20000 N5 4 0.603528 0.391151 0.717418 11.00000 0.01957 0.01277 = 0.01730 -0.00216 -0.00171 -0.00387 N6 4 0.732674 0.386497 0.852290 11.00000 0.02542 0.01757 = 0.02041 -0.00338 -0.00762 -0.00251 H6 2 0.735895 0.459814 0.842143 11.00000 -1.20000 N7 4 0.357634 0.911591 0.812631 11.00000 0.02493 0.01880 = 0.02044 -0.00475 -0.00735 -0.00476 N8 4 0.301109 0.796360 0.549316 11.00000 0.02744 0.02768 = 0.01724 -0.00021 -0.00351 -0.00546 N9 4 0.229096 0.586894 0.828213 11.00000 0.02220 0.01630 = 0.02029 -0.00235 -0.00089 -0.00608 C1 1 0.713442 0.674469 0.962225 11.00000 0.02240 0.02446 = 0.02201 -0.00188 -0.00095 -0.00673 AFIX 43 H1 2 0.662488 0.613356 0.994304 11.00000 -1.20000 AFIX 0 C2 1 0.765054 0.736663 1.016202 11.00000 0.02794 0.03317 = 0.02072 -0.00668 -0.00314 -0.00648 AFIX 43 H2A 2 0.749677 0.717443 1.085083 11.00000 -1.20000 AFIX 0 C3 1 0.839059 0.826830 0.971611 11.00000 0.02346 0.02589 = 0.03010 -0.01159 -0.00556 -0.00475 AFIX 43 H3 2 0.872195 0.870629 1.009227 11.00000 -1.20000 AFIX 0 C4 1 0.863470 0.851472 0.871213 11.00000 0.01686 0.02036 = 0.02994 -0.00900 -0.00360 -0.00358 C5 1 0.810714 0.783832 0.819290 11.00000 0.01624 0.02037 = 0.02107 -0.00392 -0.00312 -0.00340 C6 1 0.930489 0.933062 0.797810 11.00000 0.02004 0.02359 = 0.03544 -0.00733 -0.00273 -0.00824 AFIX 43 H6A 2 0.976783 0.991882 0.808210 11.00000 -1.20000 AFIX 0 C7 1 0.915861 0.911095 0.710659 11.00000 0.02070 0.02356 = 0.03057 -0.00269 -0.00122 -0.00853 AFIX 43 H7 2 0.949878 0.953564 0.649482 11.00000 -1.20000 AFIX 0 C8 1 0.779761 0.852207 0.455559 11.00000 0.02400 0.01587 = 0.02406 -0.00232 -0.00151 -0.00718 AFIX 43 H8 2 0.742889 0.921548 0.488867 11.00000 -1.20000 AFIX 0 C9 1 0.850013 0.862205 0.358037 11.00000 0.02957 0.02013 = 0.02393 0.00079 -0.00194 -0.01111 AFIX 43 H9 2 0.859729 0.938931 0.325285 11.00000 -1.20000 AFIX 0 C10 1 0.906568 0.763455 0.306835 11.00000 0.02539 0.02607 = 0.01800 -0.00138 -0.00001 -0.00997 AFIX 43 H10 2 0.956352 0.771019 0.240073 11.00000 -1.20000 AFIX 0 C11 1 0.888109 0.652252 0.356469 11.00000 0.01796 0.02248 = 0.01806 -0.00480 -0.00202 -0.00646 C12 1 0.813676 0.647544 0.455490 11.00000 0.01531 0.01632 = 0.01976 -0.00265 -0.00287 -0.00540 C13 1 0.922625 0.532568 0.333615 11.00000 0.02339 0.02520 = 0.02172 -0.00989 0.00000 -0.00784 AFIX 43 H13 2 0.973504 0.505058 0.272330 11.00000 -1.20000 AFIX 0 C14 1 0.868994 0.465289 0.416057 11.00000 0.02161 0.02062 = 0.02715 -0.00912 -0.00268 -0.00713 AFIX 43 H14 2 0.876248 0.381862 0.421160 11.00000 -1.20000 AFIX 0 C15 1 0.532502 0.332360 0.675466 11.00000 0.02355 0.02134 = 0.02232 -0.00520 -0.00574 -0.00454 AFIX 43 H15 2 0.490327 0.369397 0.616853 11.00000 -1.20000 AFIX 0 C16 1 0.520437 0.218076 0.717199 11.00000 0.02406 0.02208 = 0.03328 -0.00833 -0.00454 -0.00777 AFIX 43 H16 2 0.469392 0.177774 0.686802 11.00000 -1.20000 AFIX 0 C17 1 0.581143 0.161306 0.802235 11.00000 0.02459 0.01636 = 0.03233 -0.00274 0.00174 -0.00573 AFIX 43 H17 2 0.573478 0.082497 0.830230 11.00000 -1.20000 AFIX 0 C18 1 0.653557 0.222871 0.845432 11.00000 0.02230 0.01757 = 0.01995 -0.00106 0.00089 -0.00190 C19 1 0.661365 0.339200 0.800582 11.00000 0.01750 0.01687 = 0.01727 -0.00375 -0.00123 -0.00177 C20 1 0.725752 0.201891 0.931052 11.00000 0.03751 0.02159 = 0.02058 0.00161 -0.00612 -0.00067 AFIX 43 H20 2 0.740936 0.130688 0.977551 11.00000 -1.20000 AFIX 0 C21 1 0.768517 0.302435 0.933579 11.00000 0.03296 0.02638 = 0.02147 -0.00503 -0.01037 0.00148 AFIX 43 H21 2 0.816335 0.313630 0.984015 11.00000 -1.20000 AFIX 0 HKLF 4 REM ow5ay_et2o_0m_a.res in P-1 REM wR2 = 0.038417, GooF = S = 1.11394, Restrained GooF = 1.11391 for all data REM R1 = 0.017392 for 6411 Fo > 4sig(Fo) and 0.019236 for all 6724 data REM 397 parameters refined using 3 restraints END WGHT 0.0089 1.0637 REM Highest difference peak 0.449, deepest hole -0.697, 1-sigma level 0.068 Q1 1 0.7790 0.7211 0.8019 11.00000 0.05 0.45 Q2 1 0.8419 0.6599 0.4037 11.00000 0.05 0.38 Q3 1 0.8894 0.7073 0.3287 11.00000 0.05 0.38 Q4 1 0.6376 0.2778 0.8274 11.00000 0.05 0.36 Q5 1 0.9238 0.8853 0.8536 11.00000 0.05 0.35 ; _shelx_res_checksum 36448 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 Gd1 Gd 0.47878(2) 0.69762(2) 0.71280(2) 0.01465(3) Uani 1 1 d . . . . . O1 O 0.68787(16) 0.63854(11) 0.81002(9) 0.0200(3) Uani 1 1 d . . . . . O2 O 0.70537(16) 0.73195(11) 0.59961(9) 0.0201(3) Uani 1 1 d . . . . . O3 O 0.62139(16) 0.50098(11) 0.67655(9) 0.0202(3) Uani 1 1 d . . . . . O4 O 0.29929(17) 0.82146(12) 0.83807(10) 0.0238(3) Uani 1 1 d . . . . . O5 O 0.48108(17) 0.90146(12) 0.74380(10) 0.0246(3) Uani 1 1 d . . . . . O6 O 0.2954(2) 1.00335(13) 0.85257(11) 0.0332(3) Uani 1 1 d . . . . . O7 O 0.30530(18) 0.86148(12) 0.60984(10) 0.0259(3) Uani 1 1 d . . . . . O8 O 0.40208(17) 0.68934(12) 0.55411(10) 0.0244(3) Uani 1 1 d . . . . . O9 O 0.2038(2) 0.83378(17) 0.49163(12) 0.0458(4) Uani 1 1 d . . . . . O10 O 0.21233(17) 0.65187(12) 0.74616(9) 0.0218(3) Uani 1 1 d . . . . . O11 O 0.37082(16) 0.56245(12) 0.85407(10) 0.0224(3) Uani 1 1 d . . . . . O12 O 0.11658(18) 0.55036(14) 0.87898(11) 0.0326(3) Uani 1 1 d . . . . . N1 N 0.73466(19) 0.69963(13) 0.86411(11) 0.0191(3) Uani 1 1 d . . . . . N2 N 0.8444(2) 0.81805(14) 0.72325(12) 0.0211(3) Uani 1 1 d D . . . . H2 H 0.816(3) 0.792(2) 0.6784(14) 0.025 Uiso 1 1 d D U . . . N3 N 0.76318(18) 0.74444(13) 0.50385(11) 0.0172(3) Uani 1 1 d . . . . . N4 N 0.80243(19) 0.53491(13) 0.49148(11) 0.0189(3) Uani 1 1 d D . . . . H4 H 0.755(3) 0.5132(19) 0.5495(12) 0.023 Uiso 1 1 d D U . . . N5 N 0.60353(18) 0.39115(12) 0.71742(11) 0.0170(3) Uani 1 1 d . . . . . N6 N 0.7327(2) 0.38650(14) 0.85229(12) 0.0214(3) Uani 1 1 d D . . . . H6 H 0.736(3) 0.4598(15) 0.8421(16) 0.026 Uiso 1 1 d D U . . . N7 N 0.3576(2) 0.91159(14) 0.81263(11) 0.0209(3) Uani 1 1 d . . . . . N8 N 0.3011(2) 0.79636(15) 0.54932(12) 0.0253(3) Uani 1 1 d . . . . . N9 N 0.22910(19) 0.58689(13) 0.82821(11) 0.0200(3) Uani 1 1 d . . . . . C1 C 0.7134(2) 0.67447(17) 0.96223(14) 0.0237(4) Uani 1 1 d . . . . . H1 H 0.662488 0.613356 0.994304 0.028 Uiso 1 1 calc R U . . . C2 C 0.7651(3) 0.73666(19) 1.01620(15) 0.0277(4) Uani 1 1 d . . . . . H2A H 0.749677 0.717443 1.085083 0.033 Uiso 1 1 calc R U . . . C3 C 0.8391(2) 0.82683(18) 0.97161(15) 0.0258(4) Uani 1 1 d . . . . . H3 H 0.872195 0.870629 1.009227 0.031 Uiso 1 1 calc R U . . . C4 C 0.8635(2) 0.85147(17) 0.87121(15) 0.0221(4) Uani 1 1 d . . . . . C5 C 0.8107(2) 0.78383(16) 0.81929(13) 0.0196(3) Uani 1 1 d . . . . . C6 C 0.9305(2) 0.93306(18) 0.79781(15) 0.0258(4) Uani 1 1 d . . . . . H6A H 0.976783 0.991882 0.808210 0.031 Uiso 1 1 calc R U . . . C7 C 0.9159(2) 0.91110(17) 0.71066(15) 0.0251(4) Uani 1 1 d . . . . . H7 H 0.949878 0.953564 0.649482 0.030 Uiso 1 1 calc R U . . . C8 C 0.7798(2) 0.85221(16) 0.45556(14) 0.0215(4) Uani 1 1 d . . . . . H8 H 0.742889 0.921548 0.488867 0.026 Uiso 1 1 calc R U . . . C9 C 0.8500(2) 0.86220(17) 0.35804(14) 0.0246(4) Uani 1 1 d . . . . . H9 H 0.859729 0.938931 0.325285 0.030 Uiso 1 1 calc R U . . . C10 C 0.9066(2) 0.76345(17) 0.30684(14) 0.0234(4) Uani 1 1 d . . . . . H10 H 0.956352 0.771019 0.240073 0.028 Uiso 1 1 calc R U . . . C11 C 0.8881(2) 0.65225(16) 0.35647(13) 0.0193(3) Uani 1 1 d . . . . . C12 C 0.8137(2) 0.64754(15) 0.45549(13) 0.0169(3) Uani 1 1 d . . . . . C13 C 0.9226(2) 0.53257(17) 0.33361(14) 0.0229(4) Uani 1 1 d . . . . . H13 H 0.973504 0.505058 0.272330 0.028 Uiso 1 1 calc R U . . . C14 C 0.8690(2) 0.46529(17) 0.41606(14) 0.0223(4) Uani 1 1 d . . . . . H14 H 0.876248 0.381862 0.421160 0.027 Uiso 1 1 calc R U . . . C15 C 0.5325(2) 0.33236(17) 0.67547(14) 0.0223(4) Uani 1 1 d . . . . . H15 H 0.490327 0.369397 0.616853 0.027 Uiso 1 1 calc R U . . . C16 C 0.5204(2) 0.21808(17) 0.71720(15) 0.0256(4) Uani 1 1 d . . . . . H16 H 0.469392 0.177774 0.686802 0.031 Uiso 1 1 calc R U . . . C17 C 0.5811(2) 0.16131(17) 0.80223(15) 0.0257(4) Uani 1 1 d . . . . . H17 H 0.573478 0.082497 0.830230 0.031 Uiso 1 1 calc R U . . . C18 C 0.6536(2) 0.22287(16) 0.84543(13) 0.0219(4) Uani 1 1 d . . . . . C19 C 0.6614(2) 0.33920(15) 0.80058(13) 0.0181(3) Uani 1 1 d . . . . . C20 C 0.7258(3) 0.20189(18) 0.93105(14) 0.0291(4) Uani 1 1 d . . . . . H20 H 0.740936 0.130688 0.977551 0.035 Uiso 1 1 calc R U . . . C21 C 0.7685(3) 0.30243(18) 0.93358(15) 0.0283(4) Uani 1 1 d . . . . . H21 H 0.816335 0.313630 0.984015 0.034 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 Gd1 0.01645(4) 0.01309(4) 0.01425(4) -0.00221(3) -0.00178(3) -0.00454(3) O1 0.0238(6) 0.0185(6) 0.0218(7) -0.0036(5) -0.0079(5) -0.0085(5) O2 0.0245(6) 0.0215(6) 0.0141(6) -0.0040(5) 0.0029(5) -0.0099(5) O3 0.0272(7) 0.0127(5) 0.0186(6) 0.0001(5) -0.0013(5) -0.0062(5) O4 0.0282(7) 0.0219(6) 0.0234(7) -0.0071(5) 0.0004(5) -0.0110(5) O5 0.0220(7) 0.0220(6) 0.0300(7) -0.0078(5) 0.0018(6) -0.0082(5) O6 0.0454(9) 0.0227(7) 0.0314(8) -0.0148(6) -0.0003(7) -0.0076(6) O7 0.0322(7) 0.0190(6) 0.0241(7) -0.0016(5) -0.0060(6) -0.0045(6) O8 0.0283(7) 0.0228(6) 0.0204(7) -0.0044(5) -0.0054(5) -0.0036(5) O9 0.0432(10) 0.0544(11) 0.0325(9) -0.0065(8) -0.0222(8) 0.0059(8) O10 0.0259(7) 0.0227(6) 0.0191(6) 0.0019(5) -0.0067(5) -0.0111(5) O11 0.0211(6) 0.0225(6) 0.0215(7) 0.0008(5) -0.0044(5) -0.0054(5) O12 0.0255(7) 0.0363(8) 0.0324(8) 0.0069(6) 0.0015(6) -0.0154(6) N1 0.0179(7) 0.0192(7) 0.0215(8) -0.0049(6) -0.0047(6) -0.0052(6) N2 0.0202(7) 0.0242(8) 0.0208(8) -0.0041(6) -0.0026(6) -0.0089(6) N3 0.0180(7) 0.0173(7) 0.0160(7) -0.0024(5) -0.0010(6) -0.0059(6) N4 0.0221(7) 0.0163(7) 0.0186(8) -0.0036(6) -0.0002(6) -0.0074(6) N5 0.0196(7) 0.0128(6) 0.0173(7) -0.0022(5) -0.0017(6) -0.0039(5) N6 0.0254(8) 0.0176(7) 0.0204(8) -0.0034(6) -0.0076(6) -0.0025(6) N7 0.0249(8) 0.0188(7) 0.0204(8) -0.0047(6) -0.0074(6) -0.0048(6) N8 0.0274(8) 0.0277(8) 0.0172(8) -0.0002(6) -0.0035(6) -0.0055(7) N9 0.0222(8) 0.0163(7) 0.0203(8) -0.0024(6) -0.0009(6) -0.0061(6) C1 0.0224(9) 0.0245(9) 0.0220(9) -0.0019(7) -0.0009(7) -0.0067(7) C2 0.0279(10) 0.0332(10) 0.0207(10) -0.0067(8) -0.0031(8) -0.0065(8) C3 0.0235(9) 0.0259(9) 0.0301(10) -0.0116(8) -0.0056(8) -0.0047(8) C4 0.0169(8) 0.0204(8) 0.0299(10) -0.0090(7) -0.0036(7) -0.0036(7) C5 0.0162(8) 0.0204(8) 0.0211(9) -0.0039(7) -0.0031(7) -0.0034(7) C6 0.0200(9) 0.0236(9) 0.0354(11) -0.0073(8) -0.0027(8) -0.0082(7) C7 0.0207(9) 0.0236(9) 0.0306(10) -0.0027(8) -0.0012(8) -0.0085(7) C8 0.0240(9) 0.0159(8) 0.0241(9) -0.0023(7) -0.0015(7) -0.0072(7) C9 0.0296(10) 0.0201(9) 0.0239(10) 0.0008(7) -0.0019(8) -0.0111(8) C10 0.0254(9) 0.0261(9) 0.0180(9) -0.0014(7) 0.0000(7) -0.0100(8) C11 0.0180(8) 0.0225(8) 0.0181(9) -0.0048(7) -0.0020(7) -0.0065(7) C12 0.0153(8) 0.0163(8) 0.0198(9) -0.0027(6) -0.0029(6) -0.0054(6) C13 0.0234(9) 0.0252(9) 0.0217(9) -0.0099(7) 0.0000(7) -0.0078(7) C14 0.0216(9) 0.0206(8) 0.0272(10) -0.0091(7) -0.0027(7) -0.0071(7) C15 0.0235(9) 0.0213(8) 0.0223(9) -0.0052(7) -0.0057(7) -0.0045(7) C16 0.0241(9) 0.0221(9) 0.0333(11) -0.0083(8) -0.0045(8) -0.0078(7) C17 0.0246(9) 0.0164(8) 0.0323(11) -0.0027(7) 0.0017(8) -0.0057(7) C18 0.0223(9) 0.0176(8) 0.0199(9) -0.0011(7) 0.0009(7) -0.0019(7) C19 0.0175(8) 0.0169(8) 0.0173(8) -0.0038(6) -0.0012(6) -0.0018(6) C20 0.0375(11) 0.0216(9) 0.0206(10) 0.0016(7) -0.0061(8) -0.0007(8) C21 0.0330(11) 0.0264(10) 0.0215(10) -0.0050(8) -0.0104(8) 0.0015(8) 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' Gd Gd -0.1653 3.9035 '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 O1 Gd1 O4 87.11(5) . . ? O1 Gd1 O5 78.71(4) . . ? O1 Gd1 O7 147.59(4) . . ? O1 Gd1 O8 147.12(4) . . ? O1 Gd1 O10 128.75(4) . . ? O1 Gd1 O11 77.20(4) . . ? O2 Gd1 O1 78.81(5) . . ? O2 Gd1 O3 79.44(4) . . ? O2 Gd1 O4 128.60(4) . . ? O2 Gd1 O5 77.33(4) . . ? O2 Gd1 O7 85.50(5) . . ? O2 Gd1 O8 77.37(5) . . ? O2 Gd1 O10 148.50(4) . . ? O2 Gd1 O11 148.06(4) . . ? O3 Gd1 O1 78.85(4) . . ? O3 Gd1 O4 145.59(4) . . ? O3 Gd1 O5 150.30(5) . . ? O3 Gd1 O7 126.01(4) . . ? O3 Gd1 O8 74.78(4) . . ? O3 Gd1 O10 90.52(5) . . ? O3 Gd1 O11 75.49(4) . . ? O4 Gd1 O5 51.38(4) . . ? O4 Gd1 O7 80.77(5) . . ? O4 Gd1 O8 125.59(5) . . ? O4 Gd1 O11 70.79(4) . . ? O7 Gd1 O5 70.21(5) . . ? O7 Gd1 O8 51.31(4) . . ? O7 Gd1 O11 125.42(4) . . ? O8 Gd1 O5 117.20(4) . . ? O10 Gd1 O4 74.04(4) . . ? O10 Gd1 O5 118.78(4) . . ? O10 Gd1 O7 76.41(4) . . ? O10 Gd1 O8 71.19(4) . . ? O10 Gd1 O11 51.69(4) . . ? O11 Gd1 O5 117.71(4) . . ? O11 Gd1 O8 113.95(4) . . ? N1 O1 Gd1 132.53(10) . . ? N3 O2 Gd1 142.11(11) . . ? N5 O3 Gd1 132.72(10) . . ? N7 O4 Gd1 97.70(10) . . ? N7 O5 Gd1 94.21(10) . . ? N8 O7 Gd1 97.05(10) . . ? N8 O8 Gd1 94.43(10) . . ? N9 O10 Gd1 97.60(10) . . ? N9 O11 Gd1 94.27(10) . . ? O1 N1 C1 121.54(15) . . ? C5 N1 O1 119.14(15) . . ? C5 N1 C1 119.25(16) . . ? C5 N2 H2 125.9(15) . . ? C5 N2 C7 106.94(16) . . ? C7 N2 H2 126.8(15) . . ? O2 N3 C8 120.85(15) . . ? O2 N3 C12 119.92(14) . . ? C12 N3 C8 119.15(15) . . ? C12 N4 H4 125.7(15) . . ? C12 N4 C14 106.84(15) . . ? C14 N4 H4 127.3(15) . . ? C15 N5 O3 121.39(15) . . ? C19 N5 O3 118.89(14) . . ? C19 N5 C15 119.70(15) . . ? C19 N6 H6 125.2(15) . . ? C19 N6 C21 106.82(16) . . ? C21 N6 H6 126.9(15) . . ? O5 N7 O4 116.52(14) . . ? O6 N7 O4 121.25(16) . . ? O6 N7 O5 122.23(16) . . ? O8 N8 O7 115.88(15) . . ? O9 N8 O7 121.93(17) . . ? O9 N8 O8 122.18(17) . . ? O10 N9 O11 116.02(14) . . ? O12 N9 O10 121.99(16) . . ? O12 N9 O11 121.98(16) . . ? N1 C1 H1 119.7 . . ? N1 C1 C2 120.62(18) . . ? C2 C1 H1 119.7 . . ? C1 C2 H2A 119.4 . . ? C1 C2 C3 121.10(19) . . ? C3 C2 H2A 119.4 . . ? C2 C3 H3 120.8 . . ? C4 C3 C2 118.46(18) . . ? C4 C3 H3 120.8 . . ? C3 C4 C5 118.17(18) . . ? C3 C4 C6 137.24(18) . . ? C5 C4 C6 104.59(17) . . ? N1 C5 C4 122.34(17) . . ? N2 C5 N1 126.98(17) . . ? N2 C5 C4 110.67(17) . . ? C4 C6 H6A 126.3 . . ? C7 C6 C4 107.34(17) . . ? C7 C6 H6A 126.3 . . ? N2 C7 H7 124.8 . . ? C6 C7 N2 110.43(18) . . ? C6 C7 H7 124.8 . . ? N3 C8 H8 119.8 . . ? N3 C8 C9 120.43(17) . . ? C9 C8 H8 119.8 . . ? C8 C9 H9 119.1 . . ? C8 C9 C10 121.75(17) . . ? C10 C9 H9 119.1 . . ? C9 C10 H10 121.1 . . ? C9 C10 C11 117.86(17) . . ? C11 C10 H10 121.1 . . ? C10 C11 C12 118.03(16) . . ? C10 C11 C13 136.79(17) . . ? C12 C11 C13 105.17(16) . . ? N3 C12 N4 126.90(16) . . ? N3 C12 C11 122.76(16) . . ? N4 C12 C11 110.34(15) . . ? C11 C13 H13 126.5 . . ? C14 C13 C11 107.00(16) . . ? C14 C13 H13 126.5 . . ? N4 C14 H14 124.7 . . ? C13 C14 N4 110.64(16) . . ? C13 C14 H14 124.7 . . ? N5 C15 H15 119.8 . . ? N5 C15 C16 120.30(18) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 119.3 . . ? C17 C16 C15 121.36(18) . . ? C17 C16 H16 119.3 . . ? C16 C17 H17 121.0 . . ? C16 C17 C18 118.00(17) . . ? C18 C17 H17 121.0 . . ? C17 C18 C19 118.39(17) . . ? C17 C18 C20 136.84(18) . . ? C19 C18 C20 104.74(17) . . ? N5 C19 N6 127.03(16) . . ? N5 C19 C18 122.22(17) . . ? N6 C19 C18 110.75(16) . . ? C18 C20 H20 126.4 . . ? C21 C20 C18 107.27(17) . . ? C21 C20 H20 126.4 . . ? N6 C21 H21 124.8 . . ? C20 C21 N6 110.38(18) . . ? C20 C21 H21 124.8 . . ? 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 Gd1 O1 2.3482(12) . ? Gd1 O2 2.3230(12) . ? Gd1 O3 2.3286(12) . ? Gd1 O4 2.4457(13) . ? Gd1 O5 2.5240(13) . ? Gd1 O7 2.4573(13) . ? Gd1 O8 2.5136(13) . ? Gd1 O10 2.4408(13) . ? Gd1 O11 2.5091(13) . ? O1 N1 1.3449(19) . ? O2 N3 1.3378(19) . ? O3 N5 1.3489(18) . ? O4 N7 1.272(2) . ? O5 N7 1.263(2) . ? O6 N7 1.223(2) . ? O7 N8 1.271(2) . ? O8 N8 1.269(2) . ? O9 N8 1.218(2) . ? O10 N9 1.2713(19) . ? O11 N9 1.274(2) . ? O12 N9 1.215(2) . ? N1 C1 1.351(2) . ? N1 C5 1.342(2) . ? N2 H2 0.867(15) . ? N2 C5 1.339(2) . ? N2 C7 1.384(2) . ? N3 C8 1.351(2) . ? N3 C12 1.344(2) . ? N4 H4 0.865(15) . ? N4 C12 1.348(2) . ? N4 C14 1.382(2) . ? N5 C15 1.342(2) . ? N5 C19 1.340(2) . ? N6 H6 0.853(15) . ? N6 C19 1.344(2) . ? N6 C21 1.384(2) . ? C1 H1 0.9500 . ? C1 C2 1.379(3) . ? C2 H2A 0.9500 . ? C2 C3 1.387(3) . ? C3 H3 0.9500 . ? C3 C4 1.382(3) . ? C4 C5 1.412(3) . ? C4 C6 1.428(3) . ? C6 H6A 0.9500 . ? C6 C7 1.354(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C8 C9 1.382(3) . ? C9 H9 0.9500 . ? C9 C10 1.383(3) . ? C10 H10 0.9500 . ? C10 C11 1.397(3) . ? C11 C12 1.409(2) . ? C11 C13 1.425(2) . ? C13 H13 0.9500 . ? C13 C14 1.358(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C15 C16 1.384(3) . ? C16 H16 0.9500 . ? C16 C17 1.383(3) . ? C17 H17 0.9500 . ? C17 C18 1.387(3) . ? C18 C19 1.405(2) . ? C18 C20 1.429(3) . ? C20 H20 0.9500 . ? C20 C21 1.355(3) . ? 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 N2 H2 O2 0.867(15) 1.969(16) 2.820(2) 167(2) . yes N4 H4 O3 0.865(15) 1.917(16) 2.769(2) 168(2) . yes N6 H6 O1 0.853(15) 1.980(16) 2.815(2) 166(2) . 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 Gd1 O1 N1 C1 113.09(17) . . . . ? Gd1 O1 N1 C5 -69.8(2) . . . . ? Gd1 O2 N3 C8 112.96(18) . . . . ? Gd1 O2 N3 C12 -70.5(2) . . . . ? Gd1 O3 N5 C15 104.28(17) . . . . ? Gd1 O3 N5 C19 -77.12(19) . . . . ? Gd1 O4 N7 O5 -4.30(16) . . . . ? Gd1 O4 N7 O6 174.99(15) . . . . ? Gd1 O5 N7 O4 4.14(15) . . . . ? Gd1 O5 N7 O6 -175.15(15) . . . . ? Gd1 O7 N8 O8 -11.57(17) . . . . ? Gd1 O7 N8 O9 167.06(17) . . . . ? Gd1 O8 N8 O7 11.25(16) . . . . ? Gd1 O8 N8 O9 -167.37(18) . . . . ? Gd1 O10 N9 O11 -6.50(15) . . . . ? Gd1 O10 N9 O12 173.44(15) . . . . ? Gd1 O11 N9 O10 6.29(15) . . . . ? Gd1 O11 N9 O12 -173.66(15) . . . . ? O1 N1 C1 C2 178.81(17) . . . . ? O1 N1 C5 N2 1.6(3) . . . . ? O1 N1 C5 C4 -179.95(15) . . . . ? O2 N3 C8 C9 175.66(17) . . . . ? O2 N3 C12 N4 5.2(3) . . . . ? O2 N3 C12 C11 -174.80(16) . . . . ? O3 N5 C15 C16 177.93(16) . . . . ? O3 N5 C19 N6 2.6(3) . . . . ? O3 N5 C19 C18 -177.35(15) . . . . ? N1 C1 C2 C3 0.3(3) . . . . ? N3 C8 C9 C10 -0.5(3) . . . . ? N5 C15 C16 C17 -0.3(3) . . . . ? C1 N1 C5 N2 178.70(17) . . . . ? C1 N1 C5 C4 -2.8(3) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C2 C3 C4 C6 179.4(2) . . . . ? C3 C4 C5 N1 1.7(3) . . . . ? C3 C4 C5 N2 -179.54(17) . . . . ? C3 C4 C6 C7 -179.4(2) . . . . ? C4 C6 C7 N2 -0.7(2) . . . . ? C5 N1 C1 C2 1.7(3) . . . . ? C5 N2 C7 C6 1.4(2) . . . . ? C5 C4 C6 C7 -0.2(2) . . . . ? C6 C4 C5 N1 -177.62(16) . . . . ? C6 C4 C5 N2 1.1(2) . . . . ? C7 N2 C5 N1 177.10(17) . . . . ? C7 N2 C5 C4 -1.5(2) . . . . ? C8 N3 C12 N4 -178.17(17) . . . . ? C8 N3 C12 C11 1.8(3) . . . . ? C8 C9 C10 C11 1.0(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C9 C10 C11 C13 178.1(2) . . . . ? C10 C11 C12 N3 -1.2(3) . . . . ? C10 C11 C12 N4 178.75(16) . . . . ? C10 C11 C13 C14 -178.2(2) . . . . ? C11 C13 C14 N4 -0.4(2) . . . . ? C12 N3 C8 C9 -0.9(3) . . . . ? C12 N4 C14 C13 0.4(2) . . . . ? C12 C11 C13 C14 0.3(2) . . . . ? C13 C11 C12 N3 179.96(16) . . . . ? C13 C11 C12 N4 0.0(2) . . . . ? C14 N4 C12 N3 179.80(17) . . . . ? C14 N4 C12 C11 -0.2(2) . . . . ? C15 N5 C19 N6 -178.79(17) . . . . ? C15 N5 C19 C18 1.3(3) . . . . ? C15 C16 C17 C18 0.6(3) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C16 C17 C18 C20 178.1(2) . . . . ? C17 C18 C19 N5 -0.9(3) . . . . ? C17 C18 C19 N6 179.13(16) . . . . ? C17 C18 C20 C21 -177.4(2) . . . . ? C18 C20 C21 N6 -1.9(2) . . . . ? C19 N5 C15 C16 -0.7(3) . . . . ? C19 N6 C21 C20 2.2(2) . . . . ? C19 C18 C20 C21 0.9(2) . . . . ? C20 C18 C19 N5 -179.57(17) . . . . ? C20 C18 C19 N6 0.5(2) . . . . ? C21 N6 C19 N5 178.46(18) . . . . ? C21 N6 C19 C18 -1.6(2) . . . . ?