Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_era20t _database_code_CSD 194286 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Elena Rybak-Akimova' 'Sergey V. Kryatov' 'Olga P. Kryatova' 'Richard J. Staples' _publ_contact_author_name 'Prof Elena Rybak-Akimova' _publ_contact_author_address ; Chemistry Tufts University 62 Talbot Ave Medford MA 02155 UNITED STATES OF AMERICA ; _publ_contact_author_email 'ERYBAKAK@EMERALD.TUFTS.EDU' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Stable supramolecular dimer of self-complementary benzo-18-crown-6 with pendant protonated amino arm ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17.50 H30 F6 N O6.50 P' _chemical_formula_weight 503.39 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' 'F' 'F' 0.0171 0.0103 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.348(6) _cell_length_b 7.9883(18) _cell_length_c 24.881(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.589(5) _cell_angle_gamma 90.00 _cell_volume 4530.3(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2104 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type 'Semi-empirical, SADABS' _exptl_absorpt_correction_T_min 0.576481 _exptl_absorpt_correction_T_max 0.942203 _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-3 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 12246 _diffrn_reflns_av_R_equivalents 0.0697 _diffrn_reflns_av_sigmaI/netI 0.0809 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3991 _reflns_number_gt 1812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1386P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3991 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1782 _refine_ls_R_factor_gt 0.0964 _refine_ls_wR_factor_ref 0.2847 _refine_ls_wR_factor_gt 0.2493 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.86257(19) 0.6930(5) 0.06564(16) 0.0529(11) Uani 1 1 d . . . O2 O 0.94354(19) 0.9378(7) 0.0539(2) 0.0737(14) Uani 1 1 d . . . O3 O 0.9439(2) 1.2769(8) 0.1022(2) 0.0991(19) Uani 1 1 d . . . O4 O 0.9061(2) 1.2591(6) 0.19829(19) 0.0720(14) Uani 1 1 d . . . O5 O 0.82213(19) 1.0252(6) 0.2002(2) 0.0704(13) Uani 1 1 d . . . O6 O 0.80929(16) 0.7284(5) 0.13723(16) 0.0495(10) Uani 1 1 d . . . N1 N 0.64289(19) 0.4657(5) -0.10260(19) 0.0485(13) Uani 1 1 d . . . H1A H 0.6169 0.4792 -0.0852 0.073 Uiso 1 1 calc R . . H1B H 0.6260 0.4121 -0.1357 0.073 Uiso 1 1 calc R . . H1C H 0.6555 0.5654 -0.1093 0.073 Uiso 1 1 calc R . . C1 C 0.7801(3) 0.6341(8) 0.0911(3) 0.0510(16) Uani 1 1 d . . . C2 C 0.7262(3) 0.5535(8) 0.0814(3) 0.0609(18) Uani 1 1 d . . . H2 H 0.7084 0.5597 0.1089 0.073 Uiso 1 1 calc R . . C3 C 0.7000(3) 0.4662(8) 0.0320(3) 0.0632(18) Uani 1 1 d . . . H3 H 0.6647 0.4117 0.0265 0.076 Uiso 1 1 calc R . . C4 C 0.7246(2) 0.4569(6) -0.0096(2) 0.0389(13) Uani 1 1 d . . . C5 C 0.6937(3) 0.3654(8) -0.0649(3) 0.073(2) Uani 1 1 d . . . H5A H 0.7210 0.3452 -0.0847 0.087 Uiso 1 1 calc R . . H5B H 0.6799 0.2580 -0.0566 0.087 Uiso 1 1 calc R . . C6 C 0.7790(3) 0.5283(8) 0.0000(3) 0.0626(19) Uani 1 1 d . . . H6 H 0.7971 0.5179 -0.0271 0.075 Uiso 1 1 calc R . . C7 C 0.8070(2) 0.6188(7) 0.0523(2) 0.0457(15) Uani 1 1 d . . . C8 C 0.8940(3) 0.6734(9) 0.0281(3) 0.070(2) Uani 1 1 d . . . H8A H 0.8720 0.7216 -0.0090 0.084 Uiso 1 1 calc R . . H8B H 0.9000 0.5554 0.0228 0.084 Uiso 1 1 calc R . . C9 C 0.9504(3) 0.7579(10) 0.0531(3) 0.078(2) Uani 1 1 d . . . H9A H 0.9699 0.7182 0.0921 0.093 Uiso 1 1 calc R . . H9B H 0.9750 0.7303 0.0311 0.093 Uiso 1 1 calc R . . C10 C 0.9959(4) 1.0325(15) 0.0785(4) 0.111(3) Uani 1 1 d . . . H10A H 1.0235 1.0043 0.0598 0.133 Uiso 1 1 calc R . . H10B H 1.0138 1.0056 0.1190 0.133 Uiso 1 1 calc R . . C11 C 0.9821(4) 1.2151(15) 0.0716(4) 0.123(4) Uani 1 1 d . . . H11A H 1.0186 1.2771 0.0851 0.147 Uiso 1 1 calc R . . H11B H 0.9632 1.2390 0.0310 0.147 Uiso 1 1 calc R . . C12 C 0.9727(4) 1.3519(10) 0.1551(4) 0.094(3) Uani 1 1 d . . . H12A H 0.9941 1.4494 0.1501 0.113 Uiso 1 1 calc R . . H12B H 1.0005 1.2739 0.1802 0.113 Uiso 1 1 calc R . . C13 C 0.9299(4) 1.4016(9) 0.1806(3) 0.086(2) Uani 1 1 d . . . H13A H 0.9486 1.4733 0.2135 0.104 Uiso 1 1 calc R . . H13B H 0.8987 1.4648 0.1529 0.104 Uiso 1 1 calc R . . C14 C 0.8595(4) 1.2991(12) 0.2192(4) 0.092(3) Uani 1 1 d . . . H14A H 0.8252 1.3373 0.1879 0.111 Uiso 1 1 calc R . . H14B H 0.8718 1.3869 0.2479 0.111 Uiso 1 1 calc R . . C15 C 0.8462(4) 1.1464(12) 0.2443(4) 0.095(3) Uani 1 1 d . . . H15A H 0.8817 1.1028 0.2728 0.114 Uiso 1 1 calc R . . H15B H 0.8184 1.1707 0.2631 0.114 Uiso 1 1 calc R . . C16 C 0.8148(3) 0.8682(9) 0.2234(3) 0.073(2) Uani 1 1 d . . . H16A H 0.7960 0.8832 0.2516 0.088 Uiso 1 1 calc R . . H16B H 0.8526 0.8154 0.2421 0.088 Uiso 1 1 calc R . . C17 C 0.7782(3) 0.7637(9) 0.1761(3) 0.0645(19) Uani 1 1 d . . . H17A H 0.7689 0.6597 0.1911 0.077 Uiso 1 1 calc R . . H17B H 0.7418 0.8213 0.1556 0.077 Uiso 1 1 calc R . . P1 P 0.63220(7) 0.1056(3) 0.13249(8) 0.0666(6) Uani 1 1 d . . . F1 F 0.5832(2) 0.1155(8) 0.0719(2) 0.142(2) Uani 1 1 d . . . F2 F 0.6282(2) -0.0945(6) 0.1300(2) 0.1189(18) Uani 1 1 d . . . F3 F 0.6802(2) 0.0943(8) 0.1033(2) 0.1250(19) Uani 1 1 d . . . F4 F 0.58458(19) 0.1130(6) 0.1626(2) 0.1052(16) Uani 1 1 d . . . F5 F 0.68117(19) 0.0852(6) 0.19386(17) 0.0936(14) Uani 1 1 d . . . F6 F 0.6360(3) 0.2979(7) 0.1358(2) 0.1246(19) Uani 1 1 d . . . C1S C 1.0000 0.851(3) 0.2500 0.163(7) Uiso 1 2 d S . . H1SA H 1.0069 0.7369 0.2630 0.195 Uiso 0.50 1 d PR . . H1SB H 0.9820 0.9261 0.2689 0.195 Uiso 0.50 1 d PR . . H1SC H 1.0320 0.9150 0.2467 0.195 Uiso 0.50 1 d PR . . O1S O 0.9705(12) 0.884(3) 0.2053(11) 0.241(10) Uiso 0.50 1 d P . . H1S H 0.9372 0.8506 0.2002 0.361 Uiso 0.50 1 calc PR . . 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 0.073(3) 0.052(3) 0.046(2) 0.014(2) 0.036(2) 0.017(2) O2 0.049(3) 0.100(4) 0.075(3) 0.024(3) 0.025(2) -0.004(3) O3 0.079(4) 0.133(5) 0.084(4) -0.007(3) 0.026(3) -0.048(3) O4 0.075(3) 0.064(3) 0.068(3) -0.010(2) 0.014(3) 0.001(2) O5 0.058(3) 0.086(4) 0.071(3) -0.014(3) 0.027(3) 0.006(2) O6 0.037(2) 0.057(3) 0.050(2) -0.001(2) 0.011(2) -0.0003(18) N1 0.040(3) 0.047(3) 0.049(3) 0.005(2) 0.003(2) -0.003(2) C1 0.048(4) 0.057(4) 0.047(4) 0.014(3) 0.014(3) 0.010(3) C2 0.040(3) 0.076(5) 0.064(4) 0.007(4) 0.016(3) -0.002(3) C3 0.048(4) 0.070(5) 0.065(4) 0.011(4) 0.011(4) 0.000(3) C4 0.036(3) 0.038(3) 0.039(3) 0.003(3) 0.009(3) 0.001(2) C5 0.065(4) 0.057(4) 0.077(5) 0.003(4) 0.001(4) 0.000(3) C6 0.052(4) 0.061(4) 0.081(5) 0.036(4) 0.031(4) 0.020(3) C7 0.041(3) 0.034(3) 0.043(3) 0.001(3) -0.009(3) -0.008(3) C8 0.070(5) 0.070(5) 0.078(5) 0.016(4) 0.038(4) 0.015(4) C9 0.076(5) 0.098(6) 0.081(5) 0.042(4) 0.055(5) 0.047(4) C10 0.071(6) 0.172(10) 0.091(6) 0.057(7) 0.030(5) 0.001(6) C11 0.109(8) 0.168(11) 0.118(8) -0.033(8) 0.074(7) -0.089(8) C12 0.083(6) 0.077(6) 0.096(6) 0.008(5) -0.002(5) -0.041(5) C13 0.092(6) 0.065(5) 0.075(5) 0.007(4) -0.004(5) -0.019(5) C14 0.083(6) 0.096(7) 0.097(6) -0.045(5) 0.031(5) 0.007(5) C15 0.087(6) 0.114(7) 0.093(6) -0.033(6) 0.041(5) 0.006(5) C16 0.073(5) 0.076(5) 0.084(5) 0.006(5) 0.044(5) 0.013(4) C17 0.051(4) 0.066(4) 0.090(5) 0.017(4) 0.041(4) 0.015(3) P1 0.0467(10) 0.0887(16) 0.0636(12) -0.0020(11) 0.0185(9) 0.0032(9) F1 0.101(4) 0.209(6) 0.085(3) -0.031(4) -0.006(3) 0.072(4) F2 0.102(4) 0.096(4) 0.142(4) -0.015(3) 0.022(3) 0.002(3) F3 0.093(3) 0.207(6) 0.096(3) 0.004(4) 0.060(3) 0.013(4) F4 0.067(3) 0.152(4) 0.111(3) -0.003(3) 0.048(3) 0.003(3) F5 0.068(3) 0.131(4) 0.072(3) -0.010(3) 0.012(2) 0.013(2) F6 0.153(5) 0.099(4) 0.126(4) 0.025(3) 0.054(4) -0.004(3) _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 O1 C7 1.406(7) . ? O1 C8 1.407(7) . ? O2 C10 1.422(10) . ? O2 C9 1.448(8) . ? O3 C12 1.390(9) . ? O3 C11 1.477(10) . ? O4 C13 1.416(8) . ? O4 C14 1.439(8) . ? O5 C16 1.418(8) . ? O5 C15 1.426(9) . ? O6 C1 1.348(7) . ? O6 C17 1.450(7) . ? N1 C5 1.495(7) . ? C1 C7 1.349(8) . ? C1 C2 1.403(8) . ? C2 C3 1.361(9) . ? C3 C4 1.369(8) . ? C4 C6 1.384(8) . ? C4 C5 1.505(8) . ? C6 C7 1.436(9) . ? C8 C9 1.460(10) . ? C10 C11 1.493(13) . ? C12 C13 1.452(11) . ? C14 C15 1.458(11) . ? C16 C17 1.462(9) . ? P1 F6 1.539(6) . ? P1 F1 1.560(5) . ? P1 F3 1.581(5) . ? P1 F5 1.581(4) . ? P1 F4 1.587(4) . ? P1 F2 1.601(5) . ? C1S O1S 1.12(3) . ? C1S O1S 1.12(3) 2_755 ? 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 C7 O1 C8 119.9(5) . . ? C10 O2 C9 116.3(6) . . ? C12 O3 C11 115.7(7) . . ? C13 O4 C14 113.2(7) . . ? C16 O5 C15 111.4(6) . . ? C1 O6 C17 115.7(5) . . ? O6 C1 C7 114.6(5) . . ? O6 C1 C2 125.8(6) . . ? C7 C1 C2 119.7(6) . . ? C3 C2 C1 120.3(6) . . ? C2 C3 C4 121.3(6) . . ? C3 C4 C6 119.7(6) . . ? C3 C4 C5 120.5(6) . . ? C6 C4 C5 119.8(6) . . ? N1 C5 C4 110.5(5) . . ? C4 C6 C7 118.9(6) . . ? C1 C7 O1 117.6(5) . . ? C1 C7 C6 120.0(6) . . ? O1 C7 C6 122.4(6) . . ? O1 C8 C9 108.4(6) . . ? O2 C9 C8 111.7(6) . . ? O2 C10 C11 109.8(7) . . ? O3 C11 C10 115.0(7) . . ? O3 C12 C13 109.4(7) . . ? O4 C13 C12 110.5(7) . . ? O4 C14 C15 106.9(7) . . ? O5 C15 C14 109.4(7) . . ? O5 C16 C17 107.8(6) . . ? O6 C17 C16 109.6(5) . . ? F6 P1 F1 90.7(3) . . ? F6 P1 F3 92.4(3) . . ? F1 P1 F3 89.8(3) . . ? F6 P1 F5 92.3(3) . . ? F1 P1 F5 176.9(3) . . ? F3 P1 F5 90.5(3) . . ? F6 P1 F4 88.7(3) . . ? F1 P1 F4 91.0(3) . . ? F3 P1 F4 178.6(3) . . ? F5 P1 F4 88.6(2) . . ? F6 P1 F2 179.1(3) . . ? F1 P1 F2 89.9(3) . . ? F3 P1 F2 88.3(3) . . ? F5 P1 F2 87.1(3) . . ? F4 P1 F2 90.6(3) . . ? O1S C1S O1S 153(4) . 2_755 ? 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 C17 O6 C1 C7 172.9(5) . . . . ? C17 O6 C1 C2 -7.7(8) . . . . ? O6 C1 C2 C3 177.7(5) . . . . ? C7 C1 C2 C3 -2.9(9) . . . . ? C1 C2 C3 C4 -1.1(10) . . . . ? C2 C3 C4 C6 4.2(9) . . . . ? C2 C3 C4 C5 -177.5(6) . . . . ? C3 C4 C5 N1 74.3(7) . . . . ? C6 C4 C5 N1 -107.4(6) . . . . ? C3 C4 C6 C7 -3.4(8) . . . . ? C5 C4 C6 C7 178.4(5) . . . . ? O6 C1 C7 O1 3.4(7) . . . . ? C2 C1 C7 O1 -176.1(5) . . . . ? O6 C1 C7 C6 -176.9(5) . . . . ? C2 C1 C7 C6 3.6(9) . . . . ? C8 O1 C7 C1 176.7(5) . . . . ? C8 O1 C7 C6 -3.0(8) . . . . ? C4 C6 C7 C1 -0.5(8) . . . . ? C4 C6 C7 O1 179.1(5) . . . . ? C7 O1 C8 C9 -178.2(5) . . . . ? C10 O2 C9 C8 178.7(6) . . . . ? O1 C8 C9 O2 -68.2(7) . . . . ? C9 O2 C10 C11 175.2(7) . . . . ? C12 O3 C11 C10 97.8(9) . . . . ? O2 C10 C11 O3 64.0(11) . . . . ? C11 O3 C12 C13 -178.4(8) . . . . ? C14 O4 C13 C12 -174.6(6) . . . . ? O3 C12 C13 O4 70.5(8) . . . . ? C13 O4 C14 C15 -170.8(6) . . . . ? C16 O5 C15 C14 173.2(6) . . . . ? O4 C14 C15 O5 -66.3(8) . . . . ? C15 O5 C16 C17 167.3(6) . . . . ? C1 O6 C17 C16 -179.3(5) . . . . ? O5 C16 C17 O6 65.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.805 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.092