#------------------------------------------------------------------------------ #$Date: 2024-10-20 01:10:19 +0300 (Sun, 20 Oct 2024) $ #$Revision: 295550 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/28/1572892.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_1572892 loop_ _publ_author_name 'Pedussaut, Lucie' 'Mahieu, Nolwenn' 'Chartier, Camille' 'Rajeshkumar, Thayalan' 'Tricoire, Maxime' 'Douair, Iskander' 'Casaretto, Nicolas' 'Maron, Laurent' 'Danoun, Gr\'egory' 'Nocton, Gr\'egory' _publ_section_title ; The photo-isomerization of the cyclononatetraenyl ligand and related rare earth complexes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC04767B _journal_year 2024 _chemical_formula_moiety 'C17 H17 Gd' _chemical_formula_sum 'C17 H17 Gd' _chemical_formula_weight 378.55 _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_Hall '-P 2ac 2n' _space_group_name_H-M_alt 'P n m a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-08-17 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2024-07-13 deposited with the CCDC. 2024-10-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.8553(8) _cell_length_b 13.0113(8) _cell_length_c 8.7412(6) _cell_measurement_reflns_used 2642 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.45 _cell_measurement_theta_min 2.81 _cell_volume 1348.36(15) _computing_cell_refinement ; X-Area Recipe 1.37.0.0 (STOE, 2021) ; _computing_data_collection ; X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022) ; _computing_data_reduction ; X-Area Integrate 2.5.3.0 (STOE, 2021) X-Area X-Red 2.3.0.0 (STOE, 2021) ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150.01 _diffrn_detector_area_resol_mean 13.33 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; 339 frames, detector distance = 60 mm ; _diffrn_measurement_device 'Eulerian 4-circle diffractometer' _diffrn_measurement_device_type 'STOE STADIVARI' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_unetI/netI 0.0688 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6971 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.103 _diffrn_reflns_theta_min 2.807 _exptl_absorpt_coefficient_mu 4.897 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.865 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 732 _exptl_crystal_size_max 0.087 _exptl_crystal_size_mid 0.045 _exptl_crystal_size_min 0.032 _refine_diff_density_max 1.383 _refine_diff_density_min -0.863 _refine_diff_density_rms 0.188 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 1552 _refine_ls_number_restraints 54 _refine_ls_restrained_S_all 0.980 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0397 _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^)+(0.0450P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.0915 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1038 _reflns_number_total 1552 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc04767b3.cif _cod_data_source_block 2-Gd-trans _cod_database_code 1572892 _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 0.859 _shelx_estimated_absorpt_t_min 0.675 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Uiso/Uaniso restraints and constraints C5 \\sim C4 \\sim C3 \\sim C2 \\sim C1B \\sim C1A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.04 within 2A C9 \\sim C8 \\sim C7 \\sim C6: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A 3. Others Sof(H2B)=1-FVAR(1) Sof(C1B)=Sof(H1B)=0.5*(1-FVAR(2)) Sof(C1A)=Sof(H1A)=0.5*FVAR(2) Sof(H2A)=FVAR(1) 4.a Aromatic/amide H refined with riding coordinates: C8(H8), C9(H9), C7(H7), C6(H6), C4(H4), C3(H3), C5(H5), C2(H2A), C2(H2B), C1A(H1A), C1B(H1B) ; _shelx_res_file ; TITL ag07_a_a.res in Pnma ag07_a.res created by SHELXL-2018/3 at 15:53:16 on 17-Aug-2023 REM Old TITL ag07_a_a.res in Pnma REM SHELXT solution in Pnma: R1 0.085, Rweak 0.003, Alpha 0.026 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C17 Gd CELL 0.71073 11.8553 13.0113 8.7412 90 90 90 ZERR 4 0.0008 0.0008 0.0006 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,-Z SYMM 0.5+X,0.5-Y,0.5-Z SFAC C H Gd UNIT 68 68 4 SIMU 0.01 0.04 2 C5 C4 C3 C2 C1B C1A SIMU 0.01 0.02 2 C9 C8 C7 C6 L.S. 12 PLAN 1 SIZE 0.087 0.045 0.032 TEMP -123.14 CONF list 4 MORE -1 BOND $H fmap 2 acta SHEL 20 0.78 OMIT 9 0 1 OMIT 8 0 2 REM REM REM WGHT 0.045000 FVAR 0.27499 0.71022 GD01 3 0.380532 0.250000 0.510489 10.50000 0.02154 0.02740 = 0.02252 0.00000 -0.00124 0.00000 C8 1 0.527774 0.379089 0.612643 11.00000 0.04613 0.04028 = 0.05154 0.01037 -0.02824 -0.02392 AFIX 43 H8 2 0.552227 0.446734 0.588704 11.00000 -1.20000 AFIX 0 C9 1 0.587898 0.304993 0.531372 11.00000 0.02657 0.08652 = 0.03249 0.01805 -0.01217 -0.02016 AFIX 43 H9 2 0.640100 0.333656 0.460811 11.00000 -1.20000 AFIX 0 C7 1 0.444104 0.379238 0.716145 11.00000 0.04443 0.05627 = 0.05147 -0.02357 -0.02873 0.00710 AFIX 43 H7 2 0.422197 0.446813 0.744625 11.00000 -1.20000 AFIX 0 C6 1 0.381586 0.303966 0.791941 11.00000 0.04197 0.10123 = 0.03097 -0.02170 -0.00325 0.01826 AFIX 43 H6 2 0.326476 0.332158 0.858754 11.00000 -1.20000 AFIX 0 C4 1 0.306105 0.391417 0.286458 11.00000 0.07835 0.07789 = 0.05662 0.04056 -0.03846 -0.02666 AFIX 43 H4 2 0.333164 0.454671 0.246461 11.00000 -1.20000 AFIX 0 C3 1 0.230516 0.407463 0.402207 11.00000 0.07770 0.06362 = 0.07733 0.01674 -0.04373 0.01608 AFIX 43 H3 2 0.223811 0.477473 0.431683 11.00000 -1.20000 AFIX 0 C5 1 0.355404 0.306372 0.209410 11.00000 0.05712 0.13503 = 0.02645 0.02870 -0.02242 -0.03145 AFIX 43 H5 2 0.404932 0.330663 0.132002 11.00000 -1.20000 AFIX 0 C2 1 0.164204 0.343958 0.482025 11.00000 0.05142 0.09284 = 0.06404 -0.01556 -0.01882 0.02462 PART 1 AFIX 43 H2A 2 0.123443 0.363139 0.571133 21.00000 -1.20000 AFIX 43 PART 2 H2B 2 0.112949 0.384520 0.539765 -21.00000 -1.20000 AFIX 0 PART 1 C1A 1 0.162668 0.250000 0.420251 20.50000 0.03665 0.08875 = 0.05938 0.00000 -0.02042 0.00000 AFIX 43 H1A 2 0.159967 0.250001 0.311633 20.50000 -1.20000 AFIX 0 PART 2 C1B 1 0.143696 0.250000 0.509986 -20.50000 0.03783 0.09115 = 0.05809 0.00000 -0.02088 0.00000 AFIX 43 H1B 2 0.087185 0.250000 0.587040 -20.50000 -1.20000 AFIX 0 HKLF 4 REM ag07_a_a.res in Pnma REM wR2 = 0.0915, GooF = S = 0.933, Restrained GooF = 0.980 for all data REM R1 = 0.0397 for 1038 Fo > 4sig(Fo) and 0.0643 for all 1552 data REM 92 parameters refined using 54 restraints END WGHT 0.0450 0.0000 REM Highest difference peak 1.383, deepest hole -0.863, 1-sigma level 0.188 Q1 1 0.4623 0.2500 0.4372 10.50000 0.05 1.38 ; _shelx_res_checksum 38962 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, 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 Gd01 Gd 0.38053(3) 0.250000 0.51049(4) 0.02382(16) Uani 1 2 d S T P A . C8 C 0.5278(7) 0.3791(6) 0.6126(8) 0.0460(18) Uani 1 1 d . U . . . H8 H 0.552227 0.446734 0.588704 0.055 Uiso 1 1 calc R U . . . C9 C 0.5879(6) 0.3050(7) 0.5314(7) 0.049(2) Uani 1 1 d . U . . . H9 H 0.640100 0.333656 0.460811 0.058 Uiso 1 1 calc R U . . . C7 C 0.4441(7) 0.3792(6) 0.7161(9) 0.0507(18) Uani 1 1 d . U . . . H7 H 0.422197 0.446813 0.744625 0.061 Uiso 1 1 calc R U . . . C6 C 0.3816(6) 0.3040(7) 0.7919(8) 0.058(2) Uani 1 1 d . U . . . H6 H 0.326476 0.332158 0.858754 0.070 Uiso 1 1 calc R U . . . C4 C 0.3061(9) 0.3914(7) 0.2865(11) 0.071(2) Uani 1 1 d . U . . . H4 H 0.333164 0.454671 0.246461 0.085 Uiso 1 1 calc R U . . . C3 C 0.2305(8) 0.4075(7) 0.4022(11) 0.073(2) Uani 1 1 d . U . . . H3 H 0.223811 0.477473 0.431683 0.087 Uiso 1 1 calc R U . . . C5 C 0.3554(7) 0.3064(7) 0.2094(9) 0.073(3) Uani 1 1 d . U . . . H5 H 0.404932 0.330663 0.132002 0.087 Uiso 1 1 calc R U . . . C2 C 0.1642(8) 0.3440(9) 0.4820(9) 0.069(2) Uani 1 1 d . U . . . H2A H 0.123443 0.363139 0.571133 0.083 Uiso 0.71(3) 1 calc R U P A 1 H2B H 0.112949 0.384520 0.539765 0.083 Uiso 0.29(3) 1 calc R U P A 2 C1A C 0.1627(15) 0.250000 0.420(3) 0.062(4) Uani 0.71(3) 2 d S TU P A 1 H1A H 0.159967 0.250001 0.311633 0.074 Uiso 0.71(3) 2 calc R U P A 1 C1B C 0.144(4) 0.250000 0.510(7) 0.062(5) Uani 0.29(3) 2 d S TU P A 2 H1B H 0.087185 0.250000 0.587040 0.075 Uiso 0.29(3) 2 calc R U P A 2 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 Gd01 0.0215(2) 0.0274(2) 0.0225(3) 0.000 -0.0012(2) 0.000 C8 0.046(4) 0.040(4) 0.052(4) 0.010(3) -0.028(3) -0.024(3) C9 0.027(3) 0.087(5) 0.032(4) 0.018(3) -0.012(3) -0.020(3) C7 0.044(4) 0.056(4) 0.051(4) -0.024(4) -0.029(4) 0.007(4) C6 0.042(5) 0.101(6) 0.031(3) -0.022(4) -0.003(4) 0.018(4) C4 0.078(6) 0.078(6) 0.057(5) 0.041(4) -0.038(4) -0.027(5) C3 0.078(6) 0.064(5) 0.077(5) 0.017(4) -0.044(5) 0.016(4) C5 0.057(6) 0.135(8) 0.026(4) 0.029(4) -0.022(4) -0.031(5) C2 0.051(4) 0.093(6) 0.064(5) -0.016(4) -0.019(4) 0.025(4) C1A 0.037(7) 0.089(8) 0.059(8) 0.000 -0.020(7) 0.000 C1B 0.038(8) 0.091(9) 0.058(9) 0.000 -0.021(9) 0.000 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' 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 C8 Gd01 C8 81.2(3) . 7_565 ? C8 Gd01 C5 125.3(3) . 7_565 ? C8 Gd01 C5 125.3(3) 7_565 . ? C8 Gd01 C5 103.3(2) . . ? C8 Gd01 C5 103.3(2) 7_565 7_565 ? C8 Gd01 C1A 138.4(2) 7_565 . ? C8 Gd01 C1A 138.4(2) . . ? C8 Gd01 C1B 132.6(6) . . ? C8 Gd01 C1B 132.6(6) 7_565 . ? C9 Gd01 C8 60.6(3) 7_565 . ? C9 Gd01 C8 60.6(3) . 7_565 ? C9 Gd01 C8 31.4(2) 7_565 7_565 ? C9 Gd01 C8 31.4(2) . . ? C9 Gd01 C9 32.4(4) 7_565 . ? C9 Gd01 C7 59.2(3) 7_565 7_565 ? C9 Gd01 C7 59.2(3) . . ? C9 Gd01 C7 81.5(2) 7_565 . ? C9 Gd01 C7 81.5(2) . 7_565 ? C9 Gd01 C5 95.6(2) . . ? C9 Gd01 C5 95.6(2) 7_565 7_565 ? C9 Gd01 C5 104.3(2) 7_565 . ? C9 Gd01 C5 104.3(2) . 7_565 ? C9 Gd01 C1A 159.5(4) . . ? C9 Gd01 C1A 159.5(4) 7_565 . ? C9 Gd01 C1B 163.3(4) . . ? C9 Gd01 C1B 163.3(4) 7_565 . ? C7 Gd01 C8 89.2(2) 7_565 . ? C7 Gd01 C8 30.2(2) . . ? C7 Gd01 C8 30.2(2) 7_565 7_565 ? C7 Gd01 C8 89.2(2) . 7_565 ? C7 Gd01 C7 81.6(4) . 7_565 ? C7 Gd01 C5 151.0(3) . 7_565 ? C7 Gd01 C5 151.0(3) 7_565 . ? C7 Gd01 C5 121.7(3) . . ? C7 Gd01 C5 121.7(3) 7_565 7_565 ? C7 Gd01 C1A 118.9(4) 7_565 . ? C7 Gd01 C1A 118.9(4) . . ? C7 Gd01 C1B 107.1(10) 7_565 . ? C7 Gd01 C1B 107.1(10) . . ? C6 Gd01 C8 59.0(2) . . ? C6 Gd01 C8 80.9(2) . 7_565 ? C6 Gd01 C8 59.0(2) 7_565 7_565 ? C6 Gd01 C8 80.9(2) 7_565 . ? C6 Gd01 C9 81.4(2) 7_565 7_565 ? C6 Gd01 C9 81.4(2) . . ? C6 Gd01 C9 90.2(2) . 7_565 ? C6 Gd01 C9 90.2(2) 7_565 . ? C6 Gd01 C7 60.4(3) 7_565 . ? C6 Gd01 C7 31.6(2) 7_565 7_565 ? C6 Gd01 C7 31.6(2) . . ? C6 Gd01 C7 60.4(3) . 7_565 ? C6 Gd01 C6 31.9(4) 7_565 . ? C6 Gd01 C5 148.0(4) 7_565 7_565 ? C6 Gd01 C5 174.0(2) . 7_565 ? C6 Gd01 C5 148.0(4) . . ? C6 Gd01 C5 174.0(2) 7_565 . ? C6 Gd01 C1A 106.6(6) 7_565 . ? C6 Gd01 C1A 106.6(6) . . ? C6 Gd01 C1B 90.4(13) . . ? C6 Gd01 C1B 90.4(13) 7_565 . ? C5 Gd01 C5 31.0(4) 7_565 . ? C5 Gd01 C1B 83.7(13) 7_565 . ? C5 Gd01 C1B 83.7(13) . . ? C1A Gd01 C5 67.5(6) . . ? C1A Gd01 C5 67.5(6) . 7_565 ? Gd01 C8 H8 137.1 . . ? C9 C8 Gd01 73.7(4) . . ? C9 C8 H8 111.9 . . ? C7 C8 Gd01 74.6(4) . . ? C7 C8 H8 111.9 . . ? C7 C8 C9 136.3(7) . . ? Gd01 C9 H9 133.4 . . ? C8 C9 Gd01 74.9(4) . . ? C8 C9 C9 133.8(4) . 7_565 ? C8 C9 H9 113.1 . . ? C9 C9 Gd01 73.8(2) 7_565 . ? C9 C9 H9 113.1 7_565 . ? Gd01 C7 H7 135.0 . . ? C8 C7 Gd01 75.2(4) . . ? C8 C7 H7 112.3 . . ? C8 C7 C6 135.3(8) . . ? C6 C7 Gd01 73.6(4) . . ? C6 C7 H7 112.3 . . ? Gd01 C6 H6 133.9 . . ? C7 C6 Gd01 74.9(4) . . ? C7 C6 C6 134.6(5) . 7_565 ? C7 C6 H6 112.7 . . ? C6 C6 Gd01 74.1(2) 7_565 . ? C6 C6 H6 112.7 7_565 . ? Gd01 C4 H4 135.5 . . ? C3 C4 Gd01 78.0(5) . . ? C3 C4 H4 111.2 . . ? C3 C4 C5 137.6(9) . . ? C5 C4 Gd01 72.1(4) . . ? C5 C4 H4 111.2 . . ? Gd01 C3 H3 130.3 . . ? C4 C3 Gd01 74.3(5) . . ? C4 C3 H3 113.7 . . ? C2 C3 Gd01 75.6(5) . . ? C2 C3 C4 132.6(10) . . ? C2 C3 H3 113.7 . . ? Gd01 C5 H5 134.7 . . ? C4 C5 Gd01 78.4(4) . . ? C4 C5 C5 141.1(5) . 7_565 ? C4 C5 H5 109.4 . . ? C5 C5 Gd01 74.5(2) 7_565 . ? C5 C5 H5 109.4 7_565 . ? Gd01 C2 H2A 119.9 . . ? Gd01 C2 H2B 140.1 . . ? C3 C2 Gd01 77.4(6) . . ? C3 C2 H2A 124.4 . . ? C3 C2 H2B 108.1 . . ? C1A C2 Gd01 69.8(8) . . ? C1A C2 C3 111.3(13) . . ? C1A C2 H2A 124.4 . . ? C1B C2 Gd01 75(2) . . ? C1B C2 C3 144(3) . . ? C1B C2 H2B 108.1 . . ? Gd01 C1A H1A 108.9 . . ? C2 C1A Gd01 82.5(8) . . ? C2 C1A Gd01 82.5(8) 7_565 . ? C2 C1A C2 132(2) . 7_565 ? C2 C1A H1A 113.8 7_565 . ? C2 C1A H1A 113.8 . . ? Gd01 C1B H1B 134.8 . . ? C2 C1B Gd01 79(2) 7_565 . ? C2 C1B Gd01 79(2) . . ? C2 C1B C2 149(6) . 7_565 ? C2 C1B H1B 105.7 . . ? C2 C1B H1B 105.7 7_565 . ? 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 Gd01 C8 2.582(6) . ? Gd01 C8 2.582(6) 7_565 ? Gd01 C9 2.567(7) 7_565 ? Gd01 C9 2.567(7) . ? Gd01 C7 2.574(7) . ? Gd01 C7 2.574(7) 7_565 ? Gd01 C6 2.558(7) 7_565 ? Gd01 C6 2.559(7) . ? Gd01 C5 2.748(7) 7_565 ? Gd01 C5 2.748(7) . ? Gd01 C1A 2.701(17) . ? Gd01 C1B 2.81(5) . ? C8 H8 0.9500 . ? C8 C9 1.394(11) . ? C8 C7 1.343(11) . ? C9 C9 1.431(18) 7_565 ? C9 H9 0.9500 . ? C7 H7 0.9500 . ? C7 C6 1.396(11) . ? C6 C6 1.404(17) 7_565 ? C6 H6 0.9500 . ? C4 H4 0.9500 . ? C4 C3 1.368(13) . ? C4 C5 1.421(12) . ? C3 H3 0.9500 . ? C3 C2 1.337(12) . ? C5 C5 1.467(19) 7_565 ? C5 H5 0.9500 . ? C2 H2A 0.9500 . ? C2 H2B 0.9500 . ? C2 C1A 1.337(15) . ? C2 C1B 1.27(2) . ? C1A H1A 0.9500 . ? C1B H1B 0.9500 . ? 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 Gd01 C8 C9 C9 -48.8(4) . . . 7_565 ? Gd01 C8 C7 C6 47.0(9) . . . . ? Gd01 C7 C6 C6 48.3(4) . . . 7_565 ? Gd01 C4 C3 C2 -52.4(10) . . . . ? Gd01 C4 C5 C5 46.4(6) . . . 7_565 ? Gd01 C3 C2 C1A -62.2(10) . . . . ? Gd01 C3 C2 C1B -41(4) . . . . ? Gd01 C2 C1A C2 72.6(19) . . . 7_565 ? Gd01 C2 C1B C2 -46(7) . . . 7_565 ? C8 C7 C6 Gd01 -47.4(9) . . . . ? C8 C7 C6 C6 0.8(12) . . . 7_565 ? C9 C8 C7 Gd01 -44.9(9) . . . . ? C9 C8 C7 C6 2.1(16) . . . . ? C7 C8 C9 Gd01 45.1(9) . . . . ? C7 C8 C9 C9 -3.7(12) . . . 7_565 ? C4 C3 C2 Gd01 52.0(10) . . . . ? C4 C3 C2 C1A -10.2(16) . . . . ? C4 C3 C2 C1B 11(4) . . . . ? C3 C4 C5 Gd01 -47.3(11) . . . . ? C3 C4 C5 C5 -0.9(16) . . . 7_565 ? C3 C2 C1A Gd01 66.9(9) . . . . ? C3 C2 C1A C2 139.5(19) . . . 7_565 ? C3 C2 C1B Gd01 42(4) . . . . ? C3 C2 C1B C2 -5(10) . . . 7_565 ? C5 C4 C3 Gd01 45.6(11) . . . . ? C5 C4 C3 C2 -6.8(19) . . . . ?