# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'M. Pudlo' 'I. Simon' 'B. Tinant' 'S. Gerard ' 'J. Sapi' _publ_contact_author_email bernard.tinant@uclouvain.be _publ_contact_author_name 'Bernard Tinant' data_sg144 _database_code_depnum_ccdc_archive 'CCDC 825601' #TrackingRef 'sg144.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 Cl N2 O2' _chemical_formula_weight 330.80 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M ' P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.071(3) _cell_length_b 9.395(3) _cell_length_c 10.422(3) _cell_angle_alpha 88.77(2) _cell_angle_beta 72.15(2) _cell_angle_gamma 77.04(2) _cell_volume 822.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.3 _exptl_crystal_description bloc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '178 images, \D\F 3\%' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15453 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2792 _reflns_number_gt 2503 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement MAR _computing_data_reduction MAR _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The data were not corrected for absorption but the collection mode take at least partially the absorption phenomena into account (see the total number of images and collected reflexions vs the number of independent reflexions). Some hydrogen atom were localized by Fourier-difference; the other ones were calculated with Afix. They were included in the refinement with an isotropic temperature factor linked to the parent C atom. ; _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^)+(0.1143P)^2^+0.3169P] 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 SHELXL _refine_ls_extinction_coef 0.26(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2792 _refine_ls_number_parameters 237 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.1944 _refine_ls_wR_factor_gt 0.1853 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 N1 N 0.2683(2) 1.3030(2) 0.3404(2) 0.0528(5) Uani 1 1 d . . . C2 C 0.1607(3) 1.2418(2) 0.3132(2) 0.0515(6) Uani 1 1 d . . . C3 C 0.2389(3) 1.1521(2) 0.1800(2) 0.0477(5) Uani 1 1 d . . . C3A C 0.4175(2) 1.1427(2) 0.1558(2) 0.0449(5) Uani 1 1 d . . . C4 C 0.5044(3) 1.0143(3) 0.2161(3) 0.0565(6) Uani 1 1 d . . . N5 N 0.5750(3) 1.0691(3) 0.2964(2) 0.0673(6) Uani 1 1 d . . . C5A C 0.5594(3) 1.2215(3) 0.2887(2) 0.0626(7) Uani 1 1 d . . . C6 C 0.6507(4) 1.3029(5) 0.3124(4) 0.0947(12) Uani 1 1 d D . . C7 C 0.6328(6) 1.4584(6) 0.2757(5) 0.1257(17) Uani 1 1 d . . . H7A H 0.6164 1.5181 0.3558 0.151 Uiso 1 1 calc R . . H7B H 0.7321 1.4687 0.2107 0.151 Uiso 1 1 calc R . . C8 C 0.5020(6) 1.5178(4) 0.2183(5) 0.1060(13) Uani 1 1 d . . . H8A H 0.4109 1.5697 0.2905 0.127 Uiso 1 1 calc R . . H8B H 0.5355 1.5887 0.1533 0.127 Uiso 1 1 calc R . . C9 C 0.4507(4) 1.4108(3) 0.1522(3) 0.0696(7) Uani 1 1 d . . . C9A C 0.4245(3) 1.2775(2) 0.2332(2) 0.0496(6) Uani 1 1 d . . . O10 O 0.5188(2) 0.8856(2) 0.1909(3) 0.0823(7) Uani 1 1 d . . . C11 C 0.6888(4) 0.9735(5) 0.3522(4) 0.1123(15) Uani 1 1 d . . . H11A H 0.7249 1.0313 0.4060 0.168 Uiso 1 1 calc R . . H11B H 0.7779 0.9223 0.2798 0.168 Uiso 1 1 calc R . . H11C H 0.6382 0.9042 0.4074 0.168 Uiso 1 1 calc R . . C12 C 0.2269(4) 1.3954(4) 0.4623(3) 0.0749(8) Uani 1 1 d . . . H12A H 0.3179 1.4302 0.4645 0.112 Uiso 1 1 calc R . . H12B H 0.1942 1.3398 0.5400 0.112 Uiso 1 1 calc R . . H12C H 0.1415 1.4771 0.4626 0.112 Uiso 1 1 calc R . . C13 C 0.1865(2) 1.0115(2) 0.1759(2) 0.0480(5) Uani 1 1 d . . . C14 C 0.1727(3) 0.9616(3) 0.0573(3) 0.0558(6) Uani 1 1 d . . . C15 C 0.1269(3) 0.8314(3) 0.0493(3) 0.0668(7) Uani 1 1 d . . . C16 C 0.0942(3) 0.7517(3) 0.1623(3) 0.0663(7) Uani 1 1 d . . . C17 C 0.1060(3) 0.7981(3) 0.2822(3) 0.0661(7) Uani 1 1 d . . . C18 C 0.1527(3) 0.9277(3) 0.2883(3) 0.0568(6) Uani 1 1 d . . . Cl19 Cl 0.02819(11) 0.59173(9) 0.15565(13) 0.1066(5) Uani 1 1 d . . . O22 O 0.0223(2) 1.2570(2) 0.3837(2) 0.0716(6) Uani 1 1 d . . . H3A H 0.477(4) 1.140(3) 0.061(3) 0.073(3) Uiso 1 1 d . . . H6 H 0.736(3) 1.254(3) 0.346(3) 0.073(3) Uiso 1 1 d D . . H9A H 0.548(4) 1.372(3) 0.067(3) 0.073(3) Uiso 1 1 d . . . H9B H 0.358(4) 1.452(3) 0.119(3) 0.073(3) Uiso 1 1 d . . . H10 H 0.213(4) 1.217(3) 0.114(3) 0.073(3) Uiso 1 1 d . . . H14 H 0.191(4) 1.020(3) -0.016(3) 0.073(3) Uiso 1 1 d . . . H15 H 0.124(4) 0.800(3) -0.033(3) 0.073(3) Uiso 1 1 d . . . H17 H 0.087(4) 0.734(3) 0.352(3) 0.073(3) Uiso 1 1 d . . . H18 H 0.166(4) 0.955(3) 0.369(3) 0.073(3) Uiso 1 1 d . . . 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 N1 0.0465(10) 0.0547(11) 0.0534(11) -0.0076(8) -0.0095(9) -0.0114(8) C2 0.0425(12) 0.0494(12) 0.0591(14) 0.0009(9) -0.0126(11) -0.0077(9) C3 0.0417(11) 0.0512(12) 0.0530(12) 0.0064(9) -0.0170(10) -0.0134(9) C3A 0.0408(11) 0.0488(11) 0.0452(12) 0.0022(8) -0.0115(10) -0.0131(8) C4 0.0396(11) 0.0590(14) 0.0636(15) 0.0097(10) -0.0083(11) -0.0083(9) N5 0.0475(11) 0.0891(16) 0.0609(13) 0.0127(10) -0.0212(11) -0.0017(10) C5A 0.0478(13) 0.0914(19) 0.0507(14) -0.0036(12) -0.0162(12) -0.0181(12) C6 0.0657(19) 0.147(3) 0.087(2) -0.016(2) -0.0332(18) -0.039(2) C7 0.130(4) 0.147(4) 0.133(4) -0.021(3) -0.044(3) -0.092(3) C8 0.133(3) 0.086(2) 0.111(3) -0.004(2) -0.024(3) -0.069(2) C9 0.0736(18) 0.0611(15) 0.0791(19) 0.0081(13) -0.0200(16) -0.0307(13) C9A 0.0454(12) 0.0553(12) 0.0499(12) 0.0001(9) -0.0141(10) -0.0161(9) O10 0.0611(12) 0.0526(11) 0.1247(18) 0.0133(10) -0.0214(12) -0.0069(8) C11 0.068(2) 0.162(4) 0.095(3) 0.034(2) -0.038(2) 0.014(2) C12 0.0715(17) 0.0829(18) 0.0649(16) -0.0223(13) -0.0094(14) -0.0209(14) C13 0.0375(10) 0.0550(12) 0.0532(13) 0.0012(9) -0.0143(10) -0.0135(8) C14 0.0434(12) 0.0694(15) 0.0546(14) -0.0017(11) -0.0135(11) -0.0145(10) C15 0.0479(13) 0.0794(17) 0.0724(17) -0.0224(14) -0.0163(13) -0.0139(12) C16 0.0408(12) 0.0609(14) 0.093(2) -0.0103(13) -0.0108(13) -0.0156(10) C17 0.0554(14) 0.0636(15) 0.0797(18) 0.0113(13) -0.0150(14) -0.0232(11) C18 0.0542(14) 0.0631(14) 0.0569(14) 0.0064(10) -0.0177(12) -0.0205(11) Cl19 0.0817(6) 0.0746(6) 0.1656(11) -0.0199(5) -0.0249(6) -0.0383(4) O22 0.0429(10) 0.0748(12) 0.0851(14) -0.0111(9) -0.0034(10) -0.0113(8) _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 N1 C2 1.338(3) . ? N1 C12 1.455(3) . ? N1 C9A 1.485(3) . ? C2 O22 1.223(3) . ? C2 C3 1.523(3) . ? C3 C13 1.507(3) . ? C3 C3A 1.543(3) . ? C3 H10 0.96(3) . ? C3A C4 1.522(3) . ? C3A C9A 1.540(3) . ? C3A H3A 0.96(3) . ? C4 O10 1.212(3) . ? C4 N5 1.368(4) . ? N5 C5A 1.410(4) . ? N5 C11 1.463(4) . ? C5A C6 1.323(4) . ? C5A C9A 1.497(3) . ? C6 C7 1.488(7) . ? C6 H6 0.97(2) . ? C7 C8 1.483(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.462(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C9A 1.518(4) . ? C9 H9A 1.04(3) . ? C9 H9B 1.00(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.381(3) . ? C13 C18 1.392(3) . ? C14 C15 1.389(4) . ? C14 H14 0.92(3) . ? C15 C16 1.373(5) . ? C15 H15 0.93(3) . ? C16 C17 1.374(4) . ? C16 Cl19 1.748(3) . ? C17 C18 1.385(4) . ? C17 H17 0.94(3) . ? C18 H18 0.94(3) . ? 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 C2 N1 C12 121.0(2) . . ? C2 N1 C9A 114.77(18) . . ? C12 N1 C9A 124.1(2) . . ? O22 C2 N1 125.3(2) . . ? O22 C2 C3 126.0(2) . . ? N1 C2 C3 108.74(19) . . ? C13 C3 C2 114.40(19) . . ? C13 C3 C3A 117.97(18) . . ? C2 C3 C3A 102.69(17) . . ? C13 C3 H10 111.9(18) . . ? C2 C3 H10 104.3(18) . . ? C3A C3 H10 104.1(19) . . ? C4 C3A C9A 103.83(18) . . ? C4 C3A C3 115.97(18) . . ? C9A C3A C3 105.49(17) . . ? C4 C3A H3A 106.6(18) . . ? C9A C3A H3A 112.1(18) . . ? C3 C3A H3A 112.7(18) . . ? O10 C4 N5 125.4(2) . . ? O10 C4 C3A 126.6(2) . . ? N5 C4 C3A 107.9(2) . . ? C4 N5 C5A 112.61(19) . . ? C4 N5 C11 121.5(3) . . ? C5A N5 C11 123.9(3) . . ? C6 C5A N5 129.1(3) . . ? C6 C5A C9A 124.2(3) . . ? N5 C5A C9A 106.5(2) . . ? C5A C6 C7 121.4(3) . . ? C5A C6 H6 116.9(19) . . ? C7 C6 H6 121.5(19) . . ? C8 C7 C6 116.2(3) . . ? C8 C7 H7A 108.2 . . ? C6 C7 H7A 108.2 . . ? C8 C7 H7B 108.2 . . ? C6 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? C9 C8 C7 116.0(4) . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8B 108.3 . . ? C7 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C8 C9 C9A 114.0(3) . . ? C8 C9 H9A 103.8(17) . . ? C9A C9 H9A 105.5(17) . . ? C8 C9 H9B 115.2(18) . . ? C9A C9 H9B 110.3(18) . . ? H9A C9 H9B 107(2) . . ? N1 C9A C5A 111.71(19) . . ? N1 C9A C9 113.3(2) . . ? C5A C9A C9 110.4(2) . . ? N1 C9A C3A 100.61(17) . . ? C5A C9A C3A 103.54(19) . . ? C9 C9A C3A 116.6(2) . . ? N5 C11 H11A 109.5 . . ? N5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 118.1(2) . . ? C14 C13 C3 119.9(2) . . ? C18 C13 C3 122.0(2) . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14 117.6(19) . . ? C15 C14 H14 120.9(19) . . ? C16 C15 C14 118.9(2) . . ? C16 C15 H15 122.4(19) . . ? C14 C15 H15 118.6(19) . . ? C15 C16 C17 121.4(2) . . ? C15 C16 Cl19 119.3(2) . . ? C17 C16 Cl19 119.2(2) . . ? C16 C17 C18 119.1(3) . . ? C16 C17 H17 115.0(18) . . ? C18 C17 H17 125.8(19) . . ? C17 C18 C13 121.1(2) . . ? C17 C18 H18 118.1(19) . . ? C13 C18 H18 120.7(19) . . ? 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 C12 N1 C2 O22 0.7(4) . . . . ? C9A N1 C2 O22 -175.1(2) . . . . ? C12 N1 C2 C3 -180.0(2) . . . . ? C9A N1 C2 C3 4.2(3) . . . . ? O22 C2 C3 C13 -38.0(3) . . . . ? N1 C2 C3 C13 142.6(2) . . . . ? O22 C2 C3 C3A -167.1(2) . . . . ? N1 C2 C3 C3A 13.6(2) . . . . ? C13 C3 C3A C4 -37.8(3) . . . . ? C2 C3 C3A C4 89.0(2) . . . . ? C13 C3 C3A C9A -152.05(19) . . . . ? C2 C3 C3A C9A -25.3(2) . . . . ? C9A C3A C4 O10 175.0(2) . . . . ? C3 C3A C4 O10 59.8(3) . . . . ? C9A C3A C4 N5 -9.7(2) . . . . ? C3 C3A C4 N5 -124.9(2) . . . . ? O10 C4 N5 C5A 169.7(2) . . . . ? C3A C4 N5 C5A -5.7(3) . . . . ? O10 C4 N5 C11 5.3(4) . . . . ? C3A C4 N5 C11 -170.1(3) . . . . ? C4 N5 C5A C6 -155.0(3) . . . . ? C11 N5 C5A C6 9.0(5) . . . . ? C4 N5 C5A C9A 19.3(3) . . . . ? C11 N5 C5A C9A -176.8(3) . . . . ? N5 C5A C6 C7 168.9(3) . . . . ? C9A C5A C6 C7 -4.4(5) . . . . ? C5A C6 C7 C8 3.2(6) . . . . ? C6 C7 C8 C9 -25.0(6) . . . . ? C7 C8 C9 C9A 47.1(5) . . . . ? C2 N1 C9A C5A -129.3(2) . . . . ? C12 N1 C9A C5A 55.1(3) . . . . ? C2 N1 C9A C9 105.3(2) . . . . ? C12 N1 C9A C9 -70.3(3) . . . . ? C2 N1 C9A C3A -20.0(2) . . . . ? C12 N1 C9A C3A 164.4(2) . . . . ? C6 C5A C9A N1 -101.8(3) . . . . ? N5 C5A C9A N1 83.6(2) . . . . ? C6 C5A C9A C9 25.2(4) . . . . ? N5 C5A C9A C9 -149.4(2) . . . . ? C6 C5A C9A C3A 150.7(3) . . . . ? N5 C5A C9A C3A -23.9(2) . . . . ? C8 C9 C9A N1 80.7(3) . . . . ? C8 C9 C9A C5A -45.4(4) . . . . ? C8 C9 C9A C3A -163.2(3) . . . . ? C4 C3A C9A N1 -95.54(19) . . . . ? C3 C3A C9A N1 26.9(2) . . . . ? C4 C3A C9A C5A 20.1(2) . . . . ? C3 C3A C9A C5A 142.50(19) . . . . ? C4 C3A C9A C9 141.5(2) . . . . ? C3 C3A C9A C9 -96.1(2) . . . . ? C2 C3 C13 C14 144.9(2) . . . . ? C3A C3 C13 C14 -94.2(3) . . . . ? C2 C3 C13 C18 -35.9(3) . . . . ? C3A C3 C13 C18 85.0(3) . . . . ? C18 C13 C14 C15 -0.1(4) . . . . ? C3 C13 C14 C15 179.1(2) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C14 C15 C16 C17 0.0(4) . . . . ? C14 C15 C16 Cl19 177.29(19) . . . . ? C15 C16 C17 C18 -0.3(4) . . . . ? Cl19 C16 C17 C18 -177.7(2) . . . . ? C16 C17 C18 C13 0.5(4) . . . . ? C14 C13 C18 C17 -0.2(4) . . . . ? C3 C13 C18 C17 -179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.346 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.096