# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2020 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_2sc _database_code_depnum_ccdc_archive 'CCDC 1960178' loop_ _audit_author_name _audit_author_address 'Filipe Almeida Paz' ;University of Aveiro CICECO Aveiro Institute of Materials Portugal ; _audit_update_record ; 2019-10-18 deposited with the CCDC. 2020-05-27 downloaded from the CCDC. ; #============================================================================= #start Validation Reply Form #============================================================================= #Alert A _vrf_PLAT029_2sc ; PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.868 Why? RESPONSE: The poor crystal quality obtained led to diffraction only to 1.00 Angstrom. No reflections were visible past this resolution. ; _vrf_PLAT414_2sc ; PROBLEM: Short Intra D-H..H-X H2A ..H7 1.79 Ang. RESPONSE: ... ; #Alert B _vrf_PLAT082_2sc ; PROBLEM: High R1 Value .................................. 0.11 Report RESPONSE: Please see response to _vrf_PLAT029_2 ; _vrf_PLAT084_2sc ; PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.28 Report RESPONSE: Please see response to _vrf_PLAT029_2 ; _vrf_PLAT094_2sc ; PROBLEM: Ratio of Maximum / Minimum Residual Density .... 2.04 Report RESPONSE: Please see response to _vrf_PLAT029_2 ; # end Validation Reply Form #============================================================================= _audit_creation_method 'SHELXL-2018/3, manual editing plus enCIFer' _audit_creation_date '26 February 2019' #============================================================================= _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H20.80 Gd2 N2 O19.40 P6' _chemical_formula_weight 931.77 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' P P 0.1023 0.0942 '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' #============================================================================= # CRYSTAL DATA #============================================================================= _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7560(17) _cell_length_b 10.186(2) _cell_length_c 12.840(3) _cell_angle_alpha 98.371(7) _cell_angle_beta 106.552(6) _cell_angle_gamma 90.234(6) _cell_volume 1208.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7109 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.50 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 2.560 _exptl_crystal_F_000 888 _exptl_transmission_factor_min 0.0565 _exptl_transmission_factor_max 0.0917 _exptl_crystal_size_max 0.080 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.020 _exptl_absorpt_coefficient_mu 5.926 _shelx_estimated_absorpt_T_min 0.649 _shelx_estimated_absorpt_T_max 0.891 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; SADABS-2016/2 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10. ; #============================================================================= # EXPERIMENTAL DATA #============================================================================= _exptl_absorpt_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'Sealed tube' _diffrn_radiation_monochromator 'Multi-layer X-ray mirror' _diffrn_measurement_device_type 'Bruker D8 QUEST ' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_reflns_number 13319 _diffrn_reflns_av_unetI/netI 0.1165 _diffrn_reflns_av_R_equivalents 0.1012 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.639 _diffrn_reflns_theta_max 25.339 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measured_fraction_theta_full 0.868 _diffrn_reflns_Laue_measured_fraction_max 0.863 _diffrn_reflns_Laue_measured_fraction_full 0.868 _diffrn_reflns_point_group_measured_fraction_max 0.863 _diffrn_reflns_point_group_measured_fraction_full 0.868 _reflns_number_total 3814 _reflns_number_gt 2578 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX3 2016.9-0 (Bruker, 2016)' _computing_cell_refinement 'SAINT V8.37a (Bruker, 2015)' _computing_data_reduction 'SAINT V8.37a (Bruker, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2015b)' #============================================================================= # REFINEMENT DATA #============================================================================= _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0205P)^2^+261.3456P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3814 _refine_ls_number_parameters 318 _refine_ls_number_restraints 204 _refine_ls_R_factor_all 0.1526 _refine_ls_R_factor_gt 0.1075 _refine_ls_wR_factor_ref 0.2833 _refine_ls_wR_factor_gt 0.2641 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================= # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS #============================================================================= 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 0.43729(16) 0.92186(16) 0.61560(14) 0.0182(5) Uani 1 1 d . U . . . Gd2 Gd 0.06218(16) 0.37937(16) 0.38290(14) 0.0184(5) Uani 1 1 d . U . . . P1 P 0.2823(9) 0.5861(8) 0.5405(7) 0.0171(19) Uani 1 1 d . U . . . P2 P 0.7092(9) 0.7244(9) 0.7861(8) 0.023(2) Uani 1 1 d . U . . . P3 P 0.5110(10) 0.2604(10) 0.7681(8) 0.029(2) Uani 1 1 d . U . . . P4 P 0.2153(8) 1.0713(8) 0.4597(7) 0.0154(18) Uani 1 1 d . U . . . P5 P -0.0024(10) 0.6650(10) 0.2273(9) 0.031(2) Uani 1 1 d . U . . . P6 P -0.2129(9) 1.1186(9) 0.2099(8) 0.022(2) Uani 1 1 d . U . . . O1 O 0.328(2) 0.723(2) 0.5269(18) 0.017(5) Uani 1 1 d . U . . . O2 O 0.127(2) 0.571(2) 0.5373(18) 0.019(5) Uani 1 1 d . U . . . O3 O 0.307(2) 0.474(2) 0.4570(18) 0.018(5) Uani 1 1 d . U . . . O4 O 0.602(3) 0.795(2) 0.711(2) 0.032(6) Uani 1 1 d . U . . . O5 O 0.749(3) 0.796(3) 0.905(2) 0.034(6) Uani 1 1 d . U . . . H5 H 0.681870 0.843230 0.914156 0.051 Uiso 1 1 calc R U . . . O6 O 0.849(2) 0.704(2) 0.761(2) 0.026(6) Uani 1 1 d . U . . . O7 O 0.645(3) 0.291(3) 0.866(2) 0.041(7) Uani 1 1 d . U . . . H7 H 0.697023 0.349935 0.854689 0.062 Uiso 1 1 calc R U . . . O8 O 0.385(3) 0.301(3) 0.809(3) 0.054(8) Uani 1 1 d . U . . . O9 O 0.510(3) 0.118(3) 0.712(3) 0.049(8) Uani 1 1 d . U . . . O10 O 0.373(2) 1.062(2) 0.4696(18) 0.015(5) Uani 1 1 d . U . . . O11 O 0.192(2) 0.9914(19) 0.5450(16) 0.012(4) Uani 1 1 d . U . . . O12 O 0.171(2) 1.213(2) 0.4735(19) 0.023(5) Uani 1 1 d . U . . . O13 O 0.004(3) 0.549(2) 0.281(2) 0.028(6) Uani 1 1 d . U . . . O14 O -0.139(4) 0.656(3) 0.128(3) 0.061(9) Uani 1 1 d . U . . . H14 H -0.121837 0.694236 0.079323 0.092 Uiso 1 1 calc R U . . . O15 O 0.122(3) 0.703(3) 0.192(3) 0.055(8) Uani 1 1 d . U . . . O16 O -0.257(3) 1.140(3) 0.086(2) 0.032(6) Uani 1 1 d . U . . . H16 H -0.345444 1.149838 0.064221 0.049 Uiso 1 1 calc R U . . . O17 O -0.350(2) 1.106(2) 0.2425(19) 0.024(5) Uani 1 1 d . U . . . O18 O -0.105(2) 1.217(2) 0.283(2) 0.026(6) Uani 1 1 d . U . . . N1 N 0.529(3) 0.506(3) 0.689(2) 0.023(7) Uani 1 1 d . U . . . H1 H 0.561816 0.535938 0.628541 0.027 Uiso 1 1 calc R U . . . N2 N -0.030(3) 0.940(3) 0.314(2) 0.021(6) Uani 1 1 d . U . . . H2 H -0.061334 0.992348 0.374291 0.025 Uiso 1 1 calc R U . . . C1 C 0.381(3) 0.562(3) 0.674(3) 0.020(7) Uani 1 1 d . U . . . H1A H 0.392433 0.648219 0.723217 0.025 Uiso 1 1 calc R U . . . H1B H 0.323159 0.501071 0.700497 0.025 Uiso 1 1 calc R U . . . C2 C 0.635(4) 0.563(3) 0.788(3) 0.027(8) Uani 1 1 d . U . . . H2A H 0.714028 0.501922 0.803561 0.033 Uiso 1 1 calc R U . . . H2B H 0.591464 0.570312 0.849339 0.033 Uiso 1 1 calc R U . . . C3 C 0.527(4) 0.357(3) 0.666(3) 0.026(8) Uani 1 1 d . U . . . H3A H 0.615992 0.332441 0.646906 0.031 Uiso 1 1 calc R U . . . H3B H 0.446382 0.327501 0.598815 0.031 Uiso 1 1 calc R U . . . C4 C 0.117(4) 0.992(4) 0.321(3) 0.028(8) Uani 1 1 d . U . . . H4A H 0.107889 1.057681 0.269391 0.033 Uiso 1 1 calc R U . . . H4B H 0.171573 0.918060 0.296788 0.033 Uiso 1 1 calc R U . . . C5 C -0.026(4) 0.794(3) 0.330(3) 0.025(8) Uani 1 1 d . U . . . H5A H -0.117046 0.771577 0.345086 0.030 Uiso 1 1 calc R U . . . H5B H 0.051503 0.788027 0.398480 0.030 Uiso 1 1 calc R U . . . C6 C -0.138(4) 0.957(3) 0.204(3) 0.023(8) Uani 1 1 d . U . . . H6A H -0.215517 0.887263 0.184487 0.027 Uiso 1 1 calc R U . . . H6B H -0.088997 0.945307 0.145122 0.027 Uiso 1 1 calc R U . . . O1W O 0.554(4) 0.826(4) 1.000(3) 0.052(10) Uiso 0.8 1 d . . P . . O2W O 0.946(6) 0.174(6) 0.001(5) 0.066(16) Uiso 0.6 1 d . . P . . 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 0.0115(9) 0.0176(10) 0.0295(11) 0.0099(8) 0.0095(7) 0.0031(6) Gd2 0.0120(9) 0.0179(10) 0.0279(11) 0.0063(8) 0.0086(7) 0.0013(6) P1 0.016(4) 0.012(4) 0.023(4) 0.001(3) 0.005(3) 0.000(3) P2 0.018(4) 0.028(5) 0.026(4) 0.008(4) 0.011(3) 0.003(3) P3 0.030(5) 0.027(5) 0.033(5) 0.008(4) 0.009(4) -0.002(4) P4 0.013(4) 0.015(4) 0.018(4) 0.003(3) 0.005(3) 0.002(3) P5 0.028(4) 0.032(5) 0.034(5) 0.010(4) 0.011(4) 0.002(4) P6 0.016(4) 0.026(4) 0.025(4) 0.006(4) 0.007(3) 0.001(3) O1 0.019(7) 0.012(8) 0.018(8) 0.004(6) 0.001(6) -0.007(6) O2 0.013(7) 0.020(8) 0.024(8) -0.001(6) 0.007(6) 0.003(6) O3 0.015(7) 0.017(8) 0.022(8) 0.002(6) 0.002(6) 0.008(6) O4 0.028(8) 0.034(9) 0.034(9) 0.001(7) 0.014(7) 0.007(7) O5 0.030(11) 0.047(13) 0.026(11) -0.001(10) 0.014(9) -0.001(10) O6 0.025(8) 0.026(8) 0.029(8) 0.007(7) 0.011(6) -0.001(6) O7 0.041(12) 0.047(13) 0.037(12) 0.004(10) 0.015(10) -0.003(10) O8 0.043(13) 0.062(14) 0.064(15) 0.013(12) 0.025(11) 0.005(11) O9 0.049(10) 0.047(10) 0.051(10) 0.006(7) 0.013(7) 0.001(7) O10 0.009(7) 0.017(8) 0.023(8) 0.009(6) 0.005(6) 0.001(6) O11 0.014(7) 0.011(7) 0.013(7) 0.010(6) 0.004(6) -0.001(6) O12 0.025(8) 0.020(8) 0.024(8) 0.007(6) 0.005(6) 0.009(6) O13 0.028(8) 0.024(8) 0.030(9) 0.010(7) 0.004(6) 0.011(6) O14 0.064(15) 0.060(15) 0.056(15) 0.018(12) 0.007(12) 0.008(12) O15 0.051(13) 0.056(14) 0.072(15) 0.005(12) 0.042(12) -0.005(11) O16 0.019(10) 0.050(13) 0.031(12) 0.016(10) 0.009(9) 0.004(9) O17 0.023(8) 0.027(8) 0.023(8) 0.004(6) 0.012(6) 0.001(6) O18 0.025(8) 0.021(8) 0.031(9) 0.002(7) 0.008(7) -0.003(6) N1 0.022(9) 0.021(9) 0.024(9) 0.003(7) 0.004(7) 0.004(7) N2 0.019(9) 0.022(9) 0.021(9) 0.009(7) 0.002(7) -0.004(7) C1 0.018(10) 0.020(10) 0.023(10) 0.005(7) 0.006(7) -0.008(7) C2 0.025(10) 0.025(11) 0.030(11) 0.003(7) 0.005(7) 0.000(7) C3 0.025(10) 0.028(11) 0.026(11) 0.002(7) 0.010(7) 0.002(7) C4 0.026(10) 0.031(11) 0.028(11) 0.007(7) 0.009(7) 0.002(7) C5 0.029(10) 0.024(10) 0.024(10) 0.006(7) 0.010(7) -0.004(7) C6 0.026(10) 0.020(10) 0.023(10) 0.006(7) 0.007(7) 0.006(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O9 2.19(3) 1_565 ? Gd1 O4 2.26(3) . ? Gd1 O1 2.27(2) . ? Gd1 O17 2.27(2) 2_576 ? Gd1 O10 2.42(2) 2_676 ? Gd1 O11 2.456(19) . ? Gd1 O10 2.46(2) . ? Gd1 P4 3.075(8) . ? Gd1 Gd1 4.034(3) 2_676 ? Gd2 O18 2.28(2) 1_545 ? Gd2 O13 2.29(2) . ? Gd2 O12 2.29(2) 1_545 ? Gd2 O6 2.31(2) 2_666 ? Gd2 O2 2.37(2) 2_566 ? Gd2 O3 2.44(2) . ? Gd2 O2 2.51(2) . ? Gd2 P1 3.064(9) . ? Gd2 Gd2 4.062(3) 2_566 ? P1 O1 1.51(2) . ? P1 O2 1.52(2) . ? P1 O3 1.52(2) . ? P1 C1 1.77(3) . ? P2 O4 1.48(3) . ? P2 O6 1.50(2) . ? P2 O5 1.53(3) . ? P2 C2 1.80(4) . ? P3 O8 1.50(3) . ? P3 O9 1.52(3) . ? P3 O7 1.53(3) . ? P3 C3 1.79(4) . ? P4 O12 1.51(2) . ? P4 O10 1.51(2) . ? P4 O11 1.52(2) . ? P4 C4 1.83(4) . ? P5 O13 1.45(3) . ? P5 O15 1.48(3) . ? P5 O14 1.55(3) . ? P5 C5 1.79(4) . ? P6 O18 1.47(2) . ? P6 O17 1.52(2) . ? P6 O16 1.58(3) . ? P6 C6 1.81(3) . ? O5 H5 0.8400 . ? O7 H7 0.8400 . ? O14 H14 0.8400 . ? O16 H16 0.8400 . ? N1 C2 1.44(4) . ? N1 C3 1.51(4) . ? N1 C1 1.52(4) . ? N1 H1 1.0000 . ? N2 C4 1.50(4) . ? N2 C5 1.53(4) . ? N2 C6 1.54(4) . ? N2 H2 1.0000 . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? 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 O9 Gd1 O4 100.2(10) 1_565 . ? O9 Gd1 O1 169.8(10) 1_565 . ? O4 Gd1 O1 83.9(8) . . ? O9 Gd1 O17 83.6(10) 1_565 2_576 ? O4 Gd1 O17 78.0(8) . 2_576 ? O1 Gd1 O17 88.1(8) . 2_576 ? O9 Gd1 O10 88.7(9) 1_565 2_676 ? O4 Gd1 O10 78.8(8) . 2_676 ? O1 Gd1 O10 101.3(8) . 2_676 ? O17 Gd1 O10 153.9(8) 2_576 2_676 ? O9 Gd1 O11 92.3(9) 1_565 . ? O4 Gd1 O11 153.0(8) . . ? O1 Gd1 O11 80.3(7) . . ? O17 Gd1 O11 79.7(7) 2_576 . ? O10 Gd1 O11 125.7(7) 2_676 . ? O9 Gd1 O10 79.6(9) 1_565 . ? O4 Gd1 O10 147.3(8) . . ? O1 Gd1 O10 102.2(7) . . ? O17 Gd1 O10 133.7(8) 2_576 . ? O10 Gd1 O10 68.5(8) 2_676 . ? O11 Gd1 O10 58.4(6) . . ? O9 Gd1 P4 85.6(8) 1_565 . ? O4 Gd1 P4 172.7(7) . . ? O1 Gd1 P4 91.2(6) . . ? O17 Gd1 P4 107.2(6) 2_576 . ? O10 Gd1 P4 97.0(5) 2_676 . ? O11 Gd1 P4 29.3(5) . . ? O10 Gd1 P4 29.1(5) . . ? O9 Gd1 Gd1 82.9(8) 1_565 2_676 ? O4 Gd1 Gd1 113.4(6) . 2_676 ? O1 Gd1 Gd1 104.3(5) . 2_676 ? O17 Gd1 Gd1 163.7(6) 2_576 2_676 ? O10 Gd1 Gd1 34.6(5) 2_676 2_676 ? O11 Gd1 Gd1 91.7(4) . 2_676 ? O10 Gd1 Gd1 33.9(5) . 2_676 ? P4 Gd1 Gd1 62.60(16) . 2_676 ? O18 Gd2 O13 101.6(9) 1_545 . ? O18 Gd2 O12 84.8(8) 1_545 1_545 ? O13 Gd2 O12 166.1(8) . 1_545 ? O18 Gd2 O6 76.5(8) 1_545 2_666 ? O13 Gd2 O6 81.5(9) . 2_666 ? O12 Gd2 O6 88.1(8) 1_545 2_666 ? O18 Gd2 O2 79.6(8) 1_545 2_566 ? O13 Gd2 O2 91.0(8) . 2_566 ? O12 Gd2 O2 102.4(8) 1_545 2_566 ? O6 Gd2 O2 152.8(8) 2_666 2_566 ? O18 Gd2 O3 153.0(8) 1_545 . ? O13 Gd2 O3 89.5(8) . . ? O12 Gd2 O3 79.7(8) 1_545 . ? O6 Gd2 O3 81.0(8) 2_666 . ? O2 Gd2 O3 125.3(7) 2_566 . ? O18 Gd2 O2 146.8(8) 1_545 . ? O13 Gd2 O2 81.6(8) . . ? O12 Gd2 O2 99.9(8) 1_545 . ? O6 Gd2 O2 136.1(7) 2_666 . ? O2 Gd2 O2 67.3(8) 2_566 . ? O3 Gd2 O2 58.7(7) . . ? O18 Gd2 P1 173.5(6) 1_545 . ? O13 Gd2 P1 83.6(6) . . ? O12 Gd2 P1 91.0(6) 1_545 . ? O6 Gd2 P1 108.4(6) 2_666 . ? O2 Gd2 P1 96.6(6) 2_566 . ? O3 Gd2 P1 29.3(5) . . ? O2 Gd2 P1 29.5(5) . . ? O18 Gd2 Gd2 114.2(6) 1_545 2_566 ? O13 Gd2 Gd2 85.4(6) . 2_566 ? O12 Gd2 Gd2 103.4(6) 1_545 2_566 ? O6 Gd2 Gd2 164.6(6) 2_666 2_566 ? O2 Gd2 Gd2 34.7(5) 2_566 2_566 ? O3 Gd2 Gd2 91.0(5) . 2_566 ? O2 Gd2 Gd2 32.6(5) . 2_566 ? P1 Gd2 Gd2 61.94(16) . 2_566 ? O1 P1 O2 114.2(13) . . ? O1 P1 O3 114.9(13) . . ? O2 P1 O3 106.2(12) . . ? O1 P1 C1 106.3(14) . . ? O2 P1 C1 105.2(14) . . ? O3 P1 C1 109.6(15) . . ? O1 P1 Gd2 130.6(9) . . ? O2 P1 Gd2 54.4(9) . . ? O3 P1 Gd2 51.9(8) . . ? C1 P1 Gd2 123.1(11) . . ? O4 P2 O6 116.4(14) . . ? O4 P2 O5 112.1(16) . . ? O6 P2 O5 104.8(14) . . ? O4 P2 C2 109.4(16) . . ? O6 P2 C2 107.5(16) . . ? O5 P2 C2 106.1(16) . . ? O8 P3 O9 117.7(18) . . ? O8 P3 O7 107.2(18) . . ? O9 P3 O7 109.8(17) . . ? O8 P3 C3 110.7(18) . . ? O9 P3 C3 103.3(17) . . ? O7 P3 C3 107.9(17) . . ? O12 P4 O10 112.7(13) . . ? O12 P4 O11 114.1(13) . . ? O10 P4 O11 104.5(12) . . ? O12 P4 C4 107.5(15) . . ? O10 P4 C4 107.2(15) . . ? O11 P4 C4 110.6(14) . . ? O12 P4 Gd1 131.0(10) . . ? O10 P4 Gd1 52.4(8) . . ? O11 P4 Gd1 52.1(8) . . ? C4 P4 Gd1 121.5(12) . . ? O13 P5 O15 118.6(18) . . ? O13 P5 O14 110.5(17) . . ? O15 P5 O14 109(2) . . ? O13 P5 C5 102.1(16) . . ? O15 P5 C5 108.9(17) . . ? O14 P5 C5 107.2(19) . . ? O18 P6 O17 115.3(14) . . ? O18 P6 O16 113.9(14) . . ? O17 P6 O16 107.5(13) . . ? O18 P6 C6 109.5(15) . . ? O17 P6 C6 107.6(15) . . ? O16 P6 C6 102.2(15) . . ? P1 O1 Gd1 145.3(13) . . ? P1 O2 Gd2 150.4(14) . 2_566 ? P1 O2 Gd2 96.1(10) . . ? Gd2 O2 Gd2 112.7(8) 2_566 . ? P1 O3 Gd2 98.8(10) . . ? P2 O4 Gd1 172.4(16) . . ? P2 O5 H5 109.5 . . ? P2 O6 Gd2 139.9(15) . 2_666 ? P3 O7 H7 109.5 . . ? P3 O9 Gd1 162.4(19) . 1_545 ? P4 O10 Gd1 147.6(13) . 2_676 ? P4 O10 Gd1 98.5(10) . . ? Gd1 O10 Gd1 111.5(8) 2_676 . ? P4 O11 Gd1 98.6(9) . . ? P4 O12 Gd2 144.8(14) . 1_565 ? P5 O13 Gd2 168.5(16) . . ? P5 O14 H14 109.5 . . ? P6 O16 H16 109.5 . . ? P6 O17 Gd1 143.8(14) . 2_576 ? P6 O18 Gd2 174.9(16) . 1_565 ? C2 N1 C3 114(3) . . ? C2 N1 C1 114(3) . . ? C3 N1 C1 114(3) . . ? C2 N1 H1 104.4 . . ? C3 N1 H1 104.4 . . ? C1 N1 H1 104.4 . . ? C4 N2 C5 110(3) . . ? C4 N2 C6 111(3) . . ? C5 N2 C6 111(2) . . ? C4 N2 H2 108.2 . . ? C5 N2 H2 108.2 . . ? C6 N2 H2 108.2 . . ? N1 C1 P1 117(2) . . ? N1 C1 H1A 107.9 . . ? P1 C1 H1A 107.9 . . ? N1 C1 H1B 107.9 . . ? P1 C1 H1B 107.9 . . ? H1A C1 H1B 107.2 . . ? N1 C2 P2 115(3) . . ? N1 C2 H2A 108.4 . . ? P2 C2 H2A 108.4 . . ? N1 C2 H2B 108.4 . . ? P2 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? N1 C3 P3 120(2) . . ? N1 C3 H3A 107.3 . . ? P3 C3 H3A 107.3 . . ? N1 C3 H3B 107.3 . . ? P3 C3 H3B 107.3 . . ? H3A C3 H3B 106.9 . . ? N2 C4 P4 113(2) . . ? N2 C4 H4A 109.1 . . ? P4 C4 H4A 109.1 . . ? N2 C4 H4B 109.1 . . ? P4 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? N2 C5 P5 122(2) . . ? N2 C5 H5A 106.9 . . ? P5 C5 H5A 106.9 . . ? N2 C5 H5B 106.9 . . ? P5 C5 H5B 106.9 . . ? H5A C5 H5B 106.7 . . ? N2 C6 P6 111(2) . . ? N2 C6 H6A 109.3 . . ? P6 C6 H6A 109.3 . . ? N2 C6 H6B 109.3 . . ? P6 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? 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 O2 P1 O1 Gd1 99(2) . . . . ? O3 P1 O1 Gd1 -138(2) . . . . ? C1 P1 O1 Gd1 -17(3) . . . . ? Gd2 P1 O1 Gd1 161.7(15) . . . . ? O1 P1 O2 Gd2 -69(3) . . . 2_566 ? O3 P1 O2 Gd2 164(2) . . . 2_566 ? C1 P1 O2 Gd2 48(3) . . . 2_566 ? Gd2 P1 O2 Gd2 168(3) . . . 2_566 ? O1 P1 O2 Gd2 123.8(11) . . . . ? O3 P1 O2 Gd2 -3.9(13) . . . . ? C1 P1 O2 Gd2 -120.1(13) . . . . ? O1 P1 O3 Gd2 -123.3(11) . . . . ? O2 P1 O3 Gd2 4.0(13) . . . . ? C1 P1 O3 Gd2 117.2(12) . . . . ? O4 P2 O6 Gd2 -53(3) . . . 2_666 ? O5 P2 O6 Gd2 -177(2) . . . 2_666 ? C2 P2 O6 Gd2 70(3) . . . 2_666 ? O8 P3 O9 Gd1 33(7) . . . 1_545 ? O7 P3 O9 Gd1 156(6) . . . 1_545 ? C3 P3 O9 Gd1 -90(7) . . . 1_545 ? O12 P4 O10 Gd1 -77(3) . . . 2_676 ? O11 P4 O10 Gd1 158(2) . . . 2_676 ? C4 P4 O10 Gd1 41(3) . . . 2_676 ? Gd1 P4 O10 Gd1 158(3) . . . 2_676 ? O12 P4 O10 Gd1 125.1(12) . . . . ? O11 P4 O10 Gd1 0.6(13) . . . . ? C4 P4 O10 Gd1 -116.8(14) . . . . ? O12 P4 O11 Gd1 -124.2(12) . . . . ? O10 P4 O11 Gd1 -0.6(13) . . . . ? C4 P4 O11 Gd1 114.4(14) . . . . ? O10 P4 O12 Gd2 101(2) . . . 1_565 ? O11 P4 O12 Gd2 -140(2) . . . 1_565 ? C4 P4 O12 Gd2 -17(3) . . . 1_565 ? Gd1 P4 O12 Gd2 160.2(15) . . . 1_565 ? O15 P5 O13 Gd2 39(9) . . . . ? O14 P5 O13 Gd2 165(8) . . . . ? C5 P5 O13 Gd2 -81(8) . . . . ? O18 P6 O17 Gd1 -51(3) . . . 2_576 ? O16 P6 O17 Gd1 -179(2) . . . 2_576 ? C6 P6 O17 Gd1 72(3) . . . 2_576 ? C2 N1 C1 P1 141(3) . . . . ? C3 N1 C1 P1 -85(3) . . . . ? O1 P1 C1 N1 -87(3) . . . . ? O2 P1 C1 N1 151(2) . . . . ? O3 P1 C1 N1 38(3) . . . . ? Gd2 P1 C1 N1 94(2) . . . . ? C3 N1 C2 P2 148(2) . . . . ? C1 N1 C2 P2 -78(3) . . . . ? O4 P2 C2 N1 29(3) . . . . ? O6 P2 C2 N1 -98(3) . . . . ? O5 P2 C2 N1 150(3) . . . . ? C2 N1 C3 P3 54(4) . . . . ? C1 N1 C3 P3 -80(3) . . . . ? O8 P3 C3 N1 52(3) . . . . ? O9 P3 C3 N1 179(3) . . . . ? O7 P3 C3 N1 -65(3) . . . . ? C5 N2 C4 P4 -93(3) . . . . ? C6 N2 C4 P4 144(2) . . . . ? O12 P4 C4 N2 -84(3) . . . . ? O10 P4 C4 N2 154(2) . . . . ? O11 P4 C4 N2 41(3) . . . . ? Gd1 P4 C4 N2 98(2) . . . . ? C4 N2 C5 P5 -72(3) . . . . ? C6 N2 C5 P5 51(3) . . . . ? O13 P5 C5 N2 176(3) . . . . ? O15 P5 C5 N2 50(3) . . . . ? O14 P5 C5 N2 -68(3) . . . . ? C4 N2 C6 P6 -87(3) . . . . ? C5 N2 C6 P6 150(2) . . . . ? O18 P6 C6 N2 34(3) . . . . ? O17 P6 C6 N2 -92(2) . . . . ? O16 P6 C6 N2 155(2) . . . . ? 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 O5 H5 O1W 0.84 1.91 2.53(5) 130.3 . yes O7 H7 O15 0.84 2.07 2.59(4) 119.3 2_666 yes O14 H14 O5 0.84 2.60 3.30(4) 141.7 1_454 yes O16 H16 O1W 0.84 2.00 2.84(5) 175.0 2_576 yes N1 H1 O3 1.00 1.90 2.81(4) 149.9 2_666 yes N2 H2 O11 1.00 1.85 2.75(3) 147.6 2_576 yes _refine_diff_density_max 4.745 _refine_diff_density_min -2.328 _refine_diff_density_rms 0.475 _shelx_res_file ; TITL RM_H6NMP58a in P-1 RM_H6NMP58a.res created by SHELXL-2018/3 at 16:36:12 on 26-Feb-2019 CELL 0.71073 9.7560 10.1857 12.8397 98.371 106.552 90.234 ZERR 2.00 0.0017 0.0020 0.0027 0.007 0.006 0.006 LATT 1 SFAC C H N O P Gd UNIT 12 41.60 4 38.80 12 4 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! REM 2.8 Water molecules of Crystallization in the unit cell REM 5.6 H-atoms added to the empirical formula L.S. 24 ACTA BOND $H CONF WPDB SHEL 5.8 0.83 SIZE 0.08 0.04 0.02 TEMP -93.150 FMAP 2 ISOR 0.008 PLAN -5 EQIV $1 -x+1, -y+1, -z+1 EQIV $2 x-1, y, z-1 EQIV $3 -x, -y+2, -z+1 HTAB O5 O1W HTAB O7 O15_$1 HTAB O14 O5_$2 HTAB O16 O1W_$3 HTAB N1 O3_$1 HTAB N2 O11_$3 HTAB WGHT 0.020500 261.345612 FVAR 0.07200 GD1 6 0.437289 0.921864 0.615603 11.00000 0.01152 0.01764 = 0.02951 0.00990 0.00946 0.00312 GD2 6 0.062179 0.379369 0.382905 11.00000 0.01198 0.01785 = 0.02792 0.00627 0.00861 0.00132 P1 5 0.282308 0.586133 0.540465 11.00000 0.01586 0.01204 = 0.02268 0.00069 0.00545 -0.00001 P2 5 0.709203 0.724361 0.786091 11.00000 0.01800 0.02805 = 0.02609 0.00766 0.01096 0.00289 P3 5 0.510970 0.260361 0.768126 11.00000 0.02985 0.02698 = 0.03263 0.00814 0.00903 -0.00246 P4 5 0.215287 1.071301 0.459700 11.00000 0.01338 0.01482 = 0.01830 0.00310 0.00474 0.00160 P5 5 -0.002423 0.665021 0.227309 11.00000 0.02827 0.03165 = 0.03445 0.01020 0.01094 0.00191 P6 5 -0.212911 1.118618 0.209854 11.00000 0.01621 0.02637 = 0.02452 0.00638 0.00740 0.00129 O1 4 0.327522 0.722915 0.526933 11.00000 0.01897 0.01250 = 0.01826 0.00398 0.00125 -0.00705 O2 4 0.126554 0.570805 0.537282 11.00000 0.01292 0.02022 = 0.02401 -0.00070 0.00653 0.00298 O3 4 0.306958 0.474030 0.457018 11.00000 0.01487 0.01657 = 0.02167 0.00204 0.00186 0.00769 O4 4 0.602243 0.795191 0.710758 11.00000 0.02824 0.03405 = 0.03434 0.00122 0.01391 0.00655 O5 4 0.749119 0.796020 0.904994 11.00000 0.02978 0.04744 = 0.02611 -0.00115 0.01352 -0.00080 AFIX 147 H5 2 0.681870 0.843230 0.914156 11.00000 -1.50000 AFIX 0 O6 4 0.849472 0.704378 0.761270 11.00000 0.02522 0.02607 = 0.02935 0.00651 0.01057 -0.00117 O7 4 0.645399 0.290623 0.866118 11.00000 0.04133 0.04738 = 0.03697 0.00375 0.01460 -0.00293 AFIX 147 H7 2 0.697023 0.349935 0.854689 11.00000 -1.50000 AFIX 0 O8 4 0.385235 0.300626 0.808943 11.00000 0.04261 0.06201 = 0.06393 0.01343 0.02496 0.00478 O9 4 0.509778 0.118320 0.712254 11.00000 0.04859 0.04741 = 0.05063 0.00617 0.01308 0.00145 O10 4 0.373279 1.062157 0.469599 11.00000 0.00913 0.01657 = 0.02308 0.00915 0.00549 0.00135 O11 4 0.191644 0.991436 0.544951 11.00000 0.01373 0.01120 = 0.01265 0.01022 0.00375 -0.00143 O12 4 0.170595 1.212658 0.473503 11.00000 0.02453 0.02045 = 0.02372 0.00707 0.00535 0.00881 O13 4 0.004484 0.548654 0.281109 11.00000 0.02772 0.02425 = 0.02969 0.01040 0.00361 0.01133 O14 4 -0.138517 0.655629 0.128260 11.00000 0.06430 0.06000 = 0.05649 0.01827 0.00714 0.00757 AFIX 147 H14 2 -0.121837 0.694236 0.079323 11.00000 -1.50000 AFIX 0 O15 4 0.122127 0.702764 0.192149 11.00000 0.05132 0.05618 = 0.07249 0.00484 0.04203 -0.00538 O16 4 -0.256969 1.139550 0.085699 11.00000 0.01947 0.05018 = 0.03142 0.01616 0.00862 0.00439 AFIX 83 H16 2 -0.345444 1.149838 0.064221 11.00000 -1.50000 AFIX 0 O17 4 -0.349565 1.105859 0.242456 11.00000 0.02341 0.02711 = 0.02328 0.00351 0.01196 0.00080 O18 4 -0.104792 1.217277 0.282903 11.00000 0.02453 0.02147 = 0.03091 0.00218 0.00810 -0.00329 N1 3 0.528828 0.506138 0.688637 11.00000 0.02186 0.02060 = 0.02411 0.00309 0.00360 0.00392 AFIX 13 H1 2 0.561816 0.535938 0.628541 11.00000 -1.20000 AFIX 0 N2 3 -0.029670 0.939971 0.313834 11.00000 0.01867 0.02171 = 0.02083 0.00851 0.00187 -0.00399 AFIX 13 H2 2 -0.061334 0.992348 0.374291 11.00000 -1.20000 AFIX 0 C1 1 0.381085 0.561771 0.674344 11.00000 0.01837 0.02027 = 0.02308 0.00464 0.00614 -0.00840 AFIX 23 H1A 2 0.392433 0.648219 0.723217 11.00000 -1.20000 H1B 2 0.323159 0.501071 0.700497 11.00000 -1.20000 AFIX 0 C2 1 0.634935 0.563405 0.787974 11.00000 0.02466 0.02520 = 0.03018 0.00347 0.00476 -0.00046 AFIX 23 H2A 2 0.714028 0.501922 0.803561 11.00000 -1.20000 H2B 2 0.591464 0.570312 0.849339 11.00000 -1.20000 AFIX 0 C3 1 0.526782 0.356747 0.665621 11.00000 0.02529 0.02787 = 0.02634 0.00243 0.00969 0.00159 AFIX 23 H3A 2 0.615992 0.332441 0.646906 11.00000 -1.20000 H3B 2 0.446382 0.327501 0.598815 11.00000 -1.20000 AFIX 0 C4 1 0.116633 0.992194 0.320566 11.00000 0.02640 0.03137 = 0.02756 0.00713 0.00944 0.00175 AFIX 23 H4A 2 0.107889 1.057681 0.269391 11.00000 -1.20000 H4B 2 0.171573 0.918060 0.296788 11.00000 -1.20000 AFIX 0 C5 1 -0.026141 0.793885 0.330379 11.00000 0.02912 0.02432 = 0.02385 0.00614 0.00980 -0.00362 AFIX 23 H5A 2 -0.117046 0.771577 0.345086 11.00000 -1.20000 H5B 2 0.051503 0.788027 0.398480 11.00000 -1.20000 AFIX 0 C6 1 -0.137539 0.956868 0.203640 11.00000 0.02626 0.02042 = 0.02300 0.00598 0.00744 0.00631 AFIX 23 H6A 2 -0.215517 0.887263 0.184487 11.00000 -1.20000 H6B 2 -0.088997 0.945307 0.145122 11.00000 -1.20000 AFIX 0 REM Water Molecules of Crystallization REM O1W 4 0.554199 0.825775 1.000137 10.80000 0.05250 O2W 4 0.945513 0.174141 0.001219 10.60000 0.06600 HKLF 4 REM RM_H6NMP58a in P-1 REM wR2 = 0.2833, GooF = S = 1.154, Restrained GooF = 1.128 for all data REM R1 = 0.1075 for 2578 Fo > 4sig(Fo) and 0.1526 for all 3814 data REM 318 parameters refined using 204 restraints END WGHT 0.0160 262.8885 REM Instructions for potential hydrogen bonds HTAB O5 O1W HTAB O7 O15_$1 HTAB O14 O5_$2 HTAB O16 O1W_$3 HTAB N1 O3_$1 HTAB N2 O11_$3 HTAB C1 O4 HTAB C1 O17_$3 HTAB C1 O8 HTAB C2 O7 HTAB C2 O15_$1 HTAB C3 O1_$1 HTAB C3 O3 EQIV $5 -x+1, -y+2, -z+1 HTAB C4 O6_$5 HTAB C4 O15 HTAB C5 O12_$3 EQIV $7 -x, -y+1, -z+1 HTAB C6 O8_$7 HTAB C6 O14 REM Highest difference peak 4.745, deepest hole -2.328, 1-sigma level 0.475 Q1 1 0.0010 0.3731 0.2628 11.00000 0.05 4.74 Q2 1 0.3849 0.9044 0.5011 11.00000 0.05 4.48 Q3 1 0.5025 0.9281 0.7548 11.00000 0.05 4.09 Q4 1 0.1237 0.3890 0.5234 11.00000 0.05 3.67 Q5 1 0.4325 0.5517 0.6198 11.00000 0.05 3.42 ; _shelx_res_checksum 22899