# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name A.Nangia P.Sanphui R.Goud U.Khandavilli S.Bhanoth _publ_contact_author_name 'Nangia, Ashwini' _publ_contact_author_email ashwini.nangia@gmail.com data_form1_P2/n _database_code_depnum_ccdc_archive 'CCDC 807904' #TrackingRef '- Form1-P2n.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 O6' _chemical_formula_weight 368.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 12.5676(11) _cell_length_b 7.0425(6) _cell_length_c 19.9582(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.9870(10) _cell_angle_gamma 90.00 _cell_volume 1759.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5264 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 26.02 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17534 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3467 _reflns_number_gt 3107 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0588P)^2^+0.9289P] 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 3467 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 O1 O -0.44868(9) 0.33201(17) 0.59957(6) 0.0266(3) Uani 1 1 d . . . O3 O 0.20619(8) 0.16171(17) 0.58225(5) 0.0256(3) Uani 1 1 d . . . O2 O -0.37987(8) 0.37142(17) 0.47761(5) 0.0268(3) Uani 1 1 d . . . O5 O 0.61142(10) 0.15764(19) 0.13497(6) 0.0281(3) Uani 1 1 d . . . O4 O 0.37389(8) 0.12713(17) 0.53026(5) 0.0272(3) Uani 1 1 d . . . O6 O 0.62082(9) -0.12337(18) 0.22696(6) 0.0313(3) Uani 1 1 d . . . C2 C -0.30349(12) 0.3308(2) 0.52833(8) 0.0210(3) Uani 1 1 d . . . C9 C 0.15710(12) 0.1981(2) 0.52342(8) 0.0203(3) Uani 1 1 d . . . C8 C 0.04270(12) 0.2347(2) 0.51892(8) 0.0213(3) Uani 1 1 d . . . H8 H 0.0053 0.2537 0.4760 0.026 Uiso 1 1 calc R . . C4 C -0.12495(12) 0.2693(2) 0.57813(8) 0.0209(3) Uani 1 1 d . . . C7 C -0.01103(12) 0.2423(2) 0.57391(8) 0.0215(3) Uani 1 1 d . . . H7 H 0.0307 0.2283 0.6156 0.026 Uiso 1 1 calc R . . C14 C 0.42425(12) 0.1959(2) 0.29626(8) 0.0237(3) Uani 1 1 d . . . C17 C 0.55052(12) 0.1662(2) 0.18783(8) 0.0230(3) Uani 1 1 d . . . C3 C -0.19574(12) 0.3078(2) 0.52144(8) 0.0206(3) Uani 1 1 d . . . H3 H -0.1696 0.3181 0.4783 0.025 Uiso 1 1 calc R . . C11 C 0.32351(12) 0.1597(2) 0.47184(8) 0.0218(3) Uani 1 1 d . . . C15 C 0.41581(13) 0.3282(2) 0.24452(8) 0.0259(4) Uani 1 1 d . . . H15 H 0.3657 0.4290 0.2455 0.031 Uiso 1 1 calc R . . C6 C -0.27344(12) 0.2752(2) 0.64750(8) 0.0230(3) Uani 1 1 d . . . H6 H -0.2998 0.2633 0.6905 0.028 Uiso 1 1 calc R . . C12 C 0.38825(12) 0.1464(2) 0.41502(8) 0.0237(3) Uani 1 1 d . . . H12 H 0.4551 0.0832 0.4220 0.028 Uiso 1 1 calc R . . C1 C -0.34272(11) 0.3134(2) 0.59188(8) 0.0215(3) Uani 1 1 d . . . C5 C -0.16530(12) 0.2540(2) 0.64088(8) 0.0225(3) Uani 1 1 d . . . H5 H -0.1179 0.2288 0.6796 0.027 Uiso 1 1 calc R . . C10 C 0.21363(12) 0.1989(2) 0.46617(8) 0.0207(3) Uani 1 1 d . . . H10 H 0.1777 0.2260 0.4234 0.025 Uiso 1 1 calc R . . C13 C 0.36076(12) 0.2165(2) 0.35390(8) 0.0239(3) Uani 1 1 d . . . H13 H 0.2954 0.2845 0.3473 0.029 Uiso 1 1 calc R . . C21 C -0.34760(13) 0.3687(3) 0.41074(8) 0.0282(4) Uani 1 1 d . . . H21A H -0.2927 0.4657 0.4063 0.042 Uiso 1 1 calc R . . H21B H -0.4094 0.3951 0.3787 0.042 Uiso 1 1 calc R . . H21C H -0.3185 0.2434 0.4013 0.042 Uiso 1 1 calc R . . C18 C 0.55589(12) 0.0264(2) 0.23825(8) 0.0235(3) Uani 1 1 d . . . C16 C 0.47940(13) 0.3150(2) 0.19146(8) 0.0254(3) Uani 1 1 d . . . H16 H 0.4742 0.4090 0.1572 0.030 Uiso 1 1 calc R . . C19 C 0.49522(12) 0.0430(2) 0.29231(7) 0.0232(3) Uani 1 1 d . . . H19 H 0.5015 -0.0495 0.3271 0.028 Uiso 1 1 calc R . . C20 C 0.62176(14) -0.2789(3) 0.27270(9) 0.0327(4) Uani 1 1 d . . . H20A H 0.6584 -0.2412 0.3160 0.049 Uiso 1 1 calc R . . H20B H 0.6594 -0.3865 0.2544 0.049 Uiso 1 1 calc R . . H20C H 0.5482 -0.3160 0.2791 0.049 Uiso 1 1 calc R . . H4A H 0.312(3) 0.125(5) 0.5636(17) 0.112(12) Uiso 1 1 d . . . H1A H -0.481(2) 0.332(4) 0.5615(13) 0.060(8) Uiso 1 1 d . . . H5A H 0.6408(18) 0.059(4) 0.1334(11) 0.047(7) 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 O1 0.0152(5) 0.0375(7) 0.0273(6) -0.0031(5) 0.0030(5) 0.0013(5) O3 0.0165(5) 0.0406(7) 0.0199(5) -0.0018(5) 0.0020(4) 0.0011(5) O2 0.0176(5) 0.0377(7) 0.0250(6) -0.0001(5) 0.0017(4) 0.0037(5) O5 0.0284(6) 0.0335(7) 0.0237(6) 0.0020(5) 0.0101(5) 0.0014(5) O4 0.0170(5) 0.0411(7) 0.0236(6) -0.0017(5) 0.0021(4) 0.0030(5) O6 0.0311(6) 0.0375(7) 0.0263(6) 0.0037(5) 0.0080(5) 0.0084(5) C2 0.0183(7) 0.0201(7) 0.0246(8) -0.0020(6) 0.0011(6) 0.0001(6) C9 0.0187(7) 0.0192(7) 0.0230(7) -0.0040(6) 0.0007(6) -0.0009(6) C8 0.0176(7) 0.0230(8) 0.0231(7) -0.0018(6) 0.0001(6) 0.0003(6) C4 0.0172(7) 0.0198(7) 0.0260(8) -0.0058(6) 0.0025(6) -0.0004(6) C7 0.0179(7) 0.0220(8) 0.0240(7) -0.0041(6) -0.0008(6) 0.0007(6) C14 0.0208(7) 0.0257(8) 0.0247(8) -0.0030(6) 0.0025(6) -0.0028(6) C17 0.0211(7) 0.0288(8) 0.0196(7) -0.0021(6) 0.0040(6) -0.0044(6) C3 0.0182(7) 0.0216(7) 0.0226(7) -0.0027(6) 0.0048(6) 0.0007(6) C11 0.0228(8) 0.0186(7) 0.0243(8) -0.0036(6) 0.0048(6) -0.0016(6) C15 0.0244(8) 0.0253(8) 0.0281(8) -0.0015(6) 0.0027(7) 0.0010(6) C6 0.0214(8) 0.0268(8) 0.0213(7) -0.0046(6) 0.0054(6) -0.0002(6) C12 0.0187(7) 0.0255(8) 0.0273(8) -0.0044(6) 0.0045(6) 0.0004(6) C1 0.0146(7) 0.0207(7) 0.0294(8) -0.0044(6) 0.0040(6) 0.0000(6) C5 0.0191(7) 0.0254(8) 0.0224(8) -0.0042(6) -0.0012(6) 0.0011(6) C10 0.0202(7) 0.0219(7) 0.0200(7) 0.0000(6) 0.0019(6) 0.0001(6) C13 0.0206(7) 0.0237(8) 0.0278(8) -0.0015(6) 0.0046(6) 0.0014(6) C21 0.0231(8) 0.0358(9) 0.0255(8) 0.0028(7) 0.0003(6) 0.0032(7) C18 0.0214(7) 0.0276(8) 0.0212(7) -0.0010(6) 0.0005(6) 0.0023(6) C16 0.0259(8) 0.0267(8) 0.0235(8) 0.0022(6) 0.0021(6) -0.0025(6) C19 0.0238(7) 0.0265(8) 0.0194(7) 0.0016(6) 0.0016(6) -0.0005(6) C20 0.0333(9) 0.0335(9) 0.0319(9) 0.0017(7) 0.0060(7) 0.0061(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 O1 C1 1.3601(18) . ? O1 H1A 0.83(3) . ? O3 C9 1.3034(19) . ? O3 H4A 1.43(3) . ? O2 C2 1.3635(18) . ? O2 C21 1.4284(19) . ? O5 C17 1.3576(18) . ? O5 H5A 0.79(3) . ? O4 C11 1.2979(19) . ? O4 H4A 1.07(3) . ? O6 C18 1.3644(19) . ? O6 C20 1.425(2) . ? C2 C3 1.382(2) . ? C2 C1 1.405(2) . ? C9 C10 1.397(2) . ? C9 C8 1.456(2) . ? C8 C7 1.339(2) . ? C8 H8 0.9500 . ? C4 C5 1.396(2) . ? C4 C3 1.404(2) . ? C4 C7 1.454(2) . ? C7 H7 0.9500 . ? C14 C15 1.388(2) . ? C14 C19 1.405(2) . ? C14 C13 1.463(2) . ? C17 C16 1.383(2) . ? C17 C18 1.405(2) . ? C3 H3 0.9500 . ? C11 C10 1.403(2) . ? C11 C12 1.455(2) . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C6 C1 1.377(2) . ? C6 C5 1.385(2) . ? C6 H6 0.9500 . ? C12 C13 1.333(2) . ? C12 H12 0.9500 . ? C5 H5 0.9500 . ? C10 H10 0.9500 . ? C13 H13 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C18 C19 1.379(2) . ? C16 H16 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C1 O1 H1A 107.2(17) . . ? C9 O3 H4A 100.2(14) . . ? C2 O2 C21 116.88(12) . . ? C17 O5 H5A 111.5(16) . . ? C11 O4 H4A 103.7(18) . . ? C18 O6 C20 117.40(12) . . ? O2 C2 C3 125.67(14) . . ? O2 C2 C1 114.13(13) . . ? C3 C2 C1 120.20(14) . . ? O3 C9 C10 120.21(13) . . ? O3 C9 C8 118.56(13) . . ? C10 C9 C8 121.23(14) . . ? C7 C8 C9 121.48(14) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C5 C4 C3 118.95(13) . . ? C5 C4 C7 118.58(14) . . ? C3 C4 C7 122.47(14) . . ? C8 C7 C4 128.47(14) . . ? C8 C7 H7 115.8 . . ? C4 C7 H7 115.8 . . ? C15 C14 C19 118.70(14) . . ? C15 C14 C13 120.47(14) . . ? C19 C14 C13 120.83(14) . . ? O5 C17 C16 119.00(14) . . ? O5 C17 C18 122.03(14) . . ? C16 C17 C18 118.96(14) . . ? C2 C3 C4 120.01(14) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? O4 C11 C10 120.46(14) . . ? O4 C11 C12 115.26(13) . . ? C10 C11 C12 124.25(14) . . ? C16 C15 C14 120.84(15) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C1 C6 C5 120.08(14) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C13 C12 C11 124.84(14) . . ? C13 C12 H12 117.6 . . ? C11 C12 H12 117.6 . . ? O1 C1 C6 118.99(14) . . ? O1 C1 C2 121.14(14) . . ? C6 C1 C2 119.86(13) . . ? C6 C5 C4 120.90(14) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C9 C10 C11 120.00(14) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C13 C14 124.54(14) . . ? C12 C13 H13 117.7 . . ? C14 C13 H13 117.7 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O6 C18 C19 125.04(14) . . ? O6 C18 C17 114.55(13) . . ? C19 C18 C17 120.36(14) . . ? C17 C16 C15 120.63(15) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C19 C14 120.39(14) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? O6 C20 H20A 109.5 . . ? O6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.327 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.051 data_Form2_Pca21 _database_code_depnum_ccdc_archive 'CCDC 807905' #TrackingRef '- Form2-Pca21 modified.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 O6' _chemical_formula_weight 368.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pca2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 35.417(3) _cell_length_b 7.7792(7) _cell_length_c 12.6482(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3484.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6973 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.89 _exptl_crystal_description Block _exptl_crystal_colour 'Dark Yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9697 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34779 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 26.02 _reflns_number_total 6854 _reflns_number_gt 6199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. This is a light atom molecule reflections were collectd using Mo-Ka radiation. Freidel pairs were merged and the Flack parameter values is therefore not meaningful. ; _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^)+(0.0663P)^2^+1.1128P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(8) _refine_ls_number_reflns 6854 _refine_ls_number_parameters 515 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 O9 O 0.58574(5) 0.3370(2) 0.64341(14) 0.0234(4) Uani 1 1 d . . . O10 O 0.64901(5) 0.4847(3) 0.66049(15) 0.0244(4) Uani 1 1 d . . . O4 O 0.64750(6) 0.9654(3) 0.44995(15) 0.0282(5) Uani 1 1 d . . . C32 C 0.65038(8) 0.4831(3) 0.5555(2) 0.0203(6) Uani 1 1 d . . . O3 O 0.58518(6) 0.8160(3) 0.43938(15) 0.0256(5) Uani 1 1 d . . . C31 C 0.62217(7) 0.4098(3) 0.4961(2) 0.0224(6) Uani 1 1 d . . . H31 H 0.6242 0.4106 0.4212 0.027 Uiso 1 1 calc R . . O6 O 0.83100(5) 1.3778(3) 0.55410(15) 0.0264(4) Uani 1 1 d . . . C18 C 0.79957(7) 1.3223(3) 0.6052(2) 0.0212(6) Uani 1 1 d . . . C30 C 0.59019(7) 0.3334(3) 0.5436(2) 0.0195(6) Uani 1 1 d . . . C10 C 0.61277(7) 0.8924(3) 0.6004(2) 0.0219(6) Uani 1 1 d . . . H10 H 0.6111 0.8946 0.6754 0.026 Uiso 1 1 calc R . . C29 C 0.56223(7) 0.2477(3) 0.4764(2) 0.0217(6) Uani 1 1 d . . . H29 H 0.5678 0.2293 0.4039 0.026 Uiso 1 1 calc R . . O7 O 0.41053(5) -0.1672(3) 0.32250(17) 0.0263(5) Uani 1 1 d . . . C19 C 0.76933(7) 1.2346(3) 0.5609(2) 0.0217(6) Uani 1 1 d . . . H19 H 0.7698 1.2066 0.4878 0.026 Uiso 1 1 calc R . . C25 C 0.49935(7) 0.1012(3) 0.4606(2) 0.0192(5) Uani 1 1 d . . . C8 C 0.55192(7) 0.7380(3) 0.5932(2) 0.0221(6) Uani 1 1 d . . . H8 H 0.5514 0.7320 0.6682 0.026 Uiso 1 1 calc R . . O11 O 0.84385(5) 0.9316(3) 0.40195(17) 0.0245(4) Uani 1 1 d . . . C28 C 0.52916(7) 0.1949(3) 0.5145(2) 0.0199(5) Uani 1 1 d . . . H28 H 0.5244 0.2220 0.5866 0.024 Uiso 1 1 calc R . . C14 C 0.73804(7) 1.1864(3) 0.6227(2) 0.0199(6) Uani 1 1 d . . . C4 C 0.48953(7) 0.5861(3) 0.5820(2) 0.0206(6) Uani 1 1 d . . . C24 C 0.46690(7) 0.0544(3) 0.5174(2) 0.0197(6) Uani 1 1 d . . . H24 H 0.4650 0.0854 0.5899 0.024 Uiso 1 1 calc R . . O12 O 0.83562(5) 0.8899(2) 0.61349(14) 0.0246(4) Uani 1 1 d . . . O2 O 0.40320(5) 0.3743(3) 0.47769(16) 0.0289(5) Uani 1 1 d . . . O5 O 0.82843(6) 1.4473(3) 0.75874(17) 0.0280(5) Uani 1 1 d . . . C35 C 0.74659(7) 0.6989(3) 0.5169(2) 0.0192(5) Uani 1 1 d . . . C2 C 0.43047(8) 0.4431(4) 0.5432(2) 0.0247(6) Uani 1 1 d D . . O1 O 0.39125(5) 0.3455(3) 0.68412(18) 0.0326(5) Uani 1 1 d D . . C22 C 0.44014(7) -0.0807(3) 0.3635(2) 0.0191(5) Uani 1 1 d . . . C7 C 0.52294(7) 0.6727(3) 0.5398(2) 0.0217(6) Uani 1 1 d . . . H7 H 0.5241 0.6835 0.4650 0.026 Uiso 1 1 calc R . . C34 C 0.71277(7) 0.6186(3) 0.5609(2) 0.0192(5) Uani 1 1 d . . . H34 H 0.7119 0.6065 0.6356 0.023 Uiso 1 1 calc R . . C33 C 0.68300(7) 0.5606(3) 0.5071(2) 0.0206(5) Uani 1 1 d . . . H33 H 0.6833 0.5711 0.4323 0.025 Uiso 1 1 calc R . . C12 C 0.67460(7) 1.0442(3) 0.6140(2) 0.0213(6) Uani 1 1 d . . . H12 H 0.6713 1.0542 0.6883 0.026 Uiso 1 1 calc R . . O8 O 0.40521(5) -0.0839(2) 0.52082(14) 0.0239(4) Uani 1 1 d . . . C40 C 0.77469(7) 0.7530(3) 0.5862(2) 0.0188(5) Uani 1 1 d . . . H40 H 0.7714 0.7359 0.6600 0.023 Uiso 1 1 calc R . . C38 C 0.81252(7) 0.8542(3) 0.4418(2) 0.0183(5) Uani 1 1 d . . . C17 C 0.79912(7) 1.3606(3) 0.7132(2) 0.0225(6) Uani 1 1 d . . . C26 C 0.50161(7) 0.0537(3) 0.3546(2) 0.0214(6) Uani 1 1 d . . . H26 H 0.5234 0.0824 0.3144 0.026 Uiso 1 1 calc R . . C36 C 0.75196(8) 0.7241(3) 0.4093(2) 0.0208(5) Uani 1 1 d . . . H36 H 0.7331 0.6878 0.3608 0.025 Uiso 1 1 calc R . . C23 C 0.43782(7) -0.0350(3) 0.4713(2) 0.0194(6) Uani 1 1 d . . . C20 C 0.83064(8) 1.3682(4) 0.4412(2) 0.0283(7) Uani 1 1 d . . . H20A H 0.8287 1.2477 0.4192 0.043 Uiso 1 1 calc R . . H20B H 0.8540 1.4179 0.4131 0.043 Uiso 1 1 calc R . . H20C H 0.8089 1.4325 0.4138 0.043 Uiso 1 1 calc R . . C3 C 0.46271(8) 0.5266(3) 0.5101(2) 0.0247(6) Uani 1 1 d . . . H3 H 0.4667 0.5439 0.4366 0.030 Uiso 1 1 calc R . . C11 C 0.64463(8) 0.9660(3) 0.5503(2) 0.0214(6) Uani 1 1 d . . . C39 C 0.80711(7) 0.8305(3) 0.5503(2) 0.0186(5) Uani 1 1 d . . . C42 C 0.40792(8) -0.1084(4) 0.6329(2) 0.0250(6) Uani 1 1 d . . . H42A H 0.4301 -0.1790 0.6490 0.038 Uiso 1 1 calc R . . H42B H 0.3851 -0.1666 0.6585 0.038 Uiso 1 1 calc R . . H42C H 0.4104 0.0035 0.6678 0.038 Uiso 1 1 calc R . . C27 C 0.47201(8) -0.0355(3) 0.3075(2) 0.0238(6) Uani 1 1 d . . . H27 H 0.4738 -0.0661 0.2349 0.029 Uiso 1 1 calc R . . C9 C 0.58423(8) 0.8179(3) 0.5431(2) 0.0218(6) Uani 1 1 d . . . C15 C 0.73874(8) 1.2264(3) 0.7303(2) 0.0241(6) Uani 1 1 d . . . H15 H 0.7180 1.1944 0.7737 0.029 Uiso 1 1 calc R . . C5 C 0.48332(8) 0.5574(3) 0.6896(2) 0.0245(6) Uani 1 1 d . . . H5 H 0.5016 0.5930 0.7399 0.029 Uiso 1 1 calc R . . C21 C 0.41135(8) 0.3689(4) 0.3666(2) 0.0289(7) Uani 1 1 d . . . H21A H 0.4144 0.4863 0.3398 0.043 Uiso 1 1 calc R . . H21B H 0.3905 0.3124 0.3293 0.043 Uiso 1 1 calc R . . H21C H 0.4347 0.3043 0.3549 0.043 Uiso 1 1 calc R . . C16 C 0.76903(8) 1.3114(4) 0.7748(2) 0.0255(6) Uani 1 1 d . . . H16 H 0.7691 1.3360 0.8484 0.031 Uiso 1 1 calc R . . C1 C 0.42393(8) 0.4221(3) 0.6506(3) 0.0272(6) Uani 1 1 d D . . C37 C 0.78457(7) 0.8018(3) 0.3720(2) 0.0216(6) Uani 1 1 d . . . H37 H 0.7878 0.8193 0.2983 0.026 Uiso 1 1 calc R . . C6 C 0.45035(8) 0.4767(4) 0.7233(2) 0.0289(6) Uani 1 1 d . . . H6 H 0.4460 0.4592 0.7966 0.035 Uiso 1 1 calc R . . C13 C 0.70633(7) 1.1015(3) 0.5702(2) 0.0214(6) Uani 1 1 d . . . H13 H 0.7087 1.0854 0.4960 0.026 Uiso 1 1 calc R . . C41 C 0.82671(8) 0.9119(4) 0.7238(2) 0.0252(6) Uani 1 1 d . . . H41A H 0.8029 0.9753 0.7307 0.038 Uiso 1 1 calc R . . H41B H 0.8470 0.9764 0.7585 0.038 Uiso 1 1 calc R . . H41C H 0.8241 0.7990 0.7574 0.038 Uiso 1 1 calc R . . H11A H 0.8578(9) 0.958(4) 0.444(3) 0.027(9) Uiso 1 1 d . . . H10A H 0.6271(12) 0.423(6) 0.680(4) 0.084(15) Uiso 1 1 d . . . H7A H 0.4164(8) -0.200(4) 0.260(3) 0.028(9) Uiso 1 1 d . . . H3A H 0.6079(11) 0.872(5) 0.423(3) 0.061(12) Uiso 1 1 d . . . H1A H 0.3779(15) 0.321(8) 0.615(3) 1.2(3) Uiso 1 1 d D . . H5A H 0.8430(7) 1.471(3) 0.710(2) 0.004(6) 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 O9 0.0226(10) 0.0243(10) 0.0232(11) 0.0022(8) 0.0015(8) -0.0054(8) O10 0.0243(10) 0.0281(11) 0.0207(10) -0.0005(8) 0.0022(8) -0.0051(8) O4 0.0288(11) 0.0339(11) 0.0218(10) 0.0015(9) 0.0006(8) -0.0052(9) C32 0.0197(14) 0.0171(13) 0.0240(14) 0.0014(11) -0.0002(11) 0.0043(10) O3 0.0221(10) 0.0283(11) 0.0263(11) -0.0009(8) -0.0003(8) -0.0036(8) C31 0.0223(13) 0.0207(13) 0.0244(14) 0.0012(11) 0.0045(12) 0.0006(11) O6 0.0217(10) 0.0344(11) 0.0230(10) -0.0021(9) 0.0009(8) -0.0031(9) C18 0.0169(13) 0.0189(13) 0.0278(15) 0.0018(11) -0.0019(11) 0.0030(10) C30 0.0193(14) 0.0144(13) 0.0249(14) 0.0013(10) 0.0005(11) 0.0052(10) C10 0.0231(13) 0.0220(14) 0.0206(14) 0.0003(11) -0.0019(12) 0.0016(11) C29 0.0189(12) 0.0225(13) 0.0237(14) 0.0028(11) 0.0006(11) 0.0017(11) O7 0.0235(10) 0.0325(11) 0.0229(11) -0.0052(9) -0.0010(9) -0.0043(8) C19 0.0246(14) 0.0196(13) 0.0207(14) 0.0011(11) -0.0013(11) 0.0033(11) C25 0.0196(12) 0.0129(12) 0.0252(14) 0.0042(10) -0.0025(11) 0.0021(10) C8 0.0211(13) 0.0225(13) 0.0226(13) 0.0008(11) -0.0002(12) 0.0026(10) O11 0.0187(10) 0.0320(11) 0.0228(10) -0.0004(9) -0.0006(9) -0.0057(9) C28 0.0235(13) 0.0186(13) 0.0176(12) 0.0035(10) -0.0013(11) 0.0025(11) C14 0.0201(13) 0.0158(13) 0.0237(14) 0.0013(10) -0.0005(11) 0.0012(10) C4 0.0202(13) 0.0169(13) 0.0246(15) -0.0003(11) 0.0011(11) 0.0027(11) C24 0.0238(14) 0.0176(13) 0.0177(13) 0.0009(11) -0.0019(11) 0.0053(11) O12 0.0200(9) 0.0330(11) 0.0206(10) -0.0016(8) -0.0023(8) -0.0036(8) O2 0.0255(10) 0.0319(11) 0.0293(11) -0.0031(9) -0.0025(9) -0.0041(9) O5 0.0275(11) 0.0346(12) 0.0220(10) -0.0039(9) 0.0018(9) -0.0099(9) C35 0.0182(13) 0.0187(13) 0.0207(13) 0.0003(11) 0.0006(11) 0.0028(10) C2 0.0176(13) 0.0200(14) 0.0366(17) 0.0002(12) -0.0032(12) 0.0022(11) O1 0.0271(11) 0.0311(11) 0.0396(12) 0.0008(9) 0.0086(9) -0.0034(9) C22 0.0161(13) 0.0176(13) 0.0235(14) 0.0015(11) -0.0030(11) 0.0005(10) C7 0.0212(14) 0.0227(14) 0.0213(14) 0.0013(11) 0.0037(11) 0.0042(11) C34 0.0239(14) 0.0159(13) 0.0176(13) -0.0018(10) 0.0017(11) 0.0015(11) C33 0.0197(13) 0.0209(13) 0.0212(14) 0.0001(11) 0.0024(11) 0.0016(11) C12 0.0237(14) 0.0171(13) 0.0230(14) -0.0002(11) -0.0002(11) 0.0040(10) O8 0.0188(10) 0.0310(11) 0.0218(10) 0.0004(8) 0.0007(8) -0.0008(8) C40 0.0228(13) 0.0193(13) 0.0144(12) 0.0005(10) -0.0023(11) 0.0040(11) C38 0.0140(12) 0.0172(13) 0.0235(14) 0.0002(10) -0.0011(10) 0.0024(10) C17 0.0229(14) 0.0164(13) 0.0283(15) -0.0026(11) -0.0038(12) 0.0013(10) C26 0.0180(13) 0.0225(14) 0.0238(14) -0.0003(11) 0.0011(11) -0.0002(11) C36 0.0191(12) 0.0186(13) 0.0247(14) -0.0014(11) -0.0037(11) -0.0027(11) C23 0.0176(12) 0.0192(13) 0.0213(14) 0.0031(11) 0.0003(11) 0.0062(10) C20 0.0234(14) 0.0365(17) 0.0252(15) -0.0003(13) 0.0011(12) -0.0056(12) C3 0.0246(14) 0.0224(14) 0.0271(15) 0.0032(12) 0.0007(12) 0.0040(11) C11 0.0232(14) 0.0177(14) 0.0233(14) 0.0006(11) -0.0007(11) 0.0040(11) C39 0.0174(13) 0.0179(13) 0.0206(13) -0.0011(11) -0.0050(11) 0.0049(10) C42 0.0246(14) 0.0271(15) 0.0234(14) 0.0001(12) 0.0016(11) -0.0001(11) C27 0.0278(14) 0.0249(14) 0.0188(13) -0.0036(11) 0.0018(11) 0.0032(12) C9 0.0239(15) 0.0206(14) 0.0209(14) 0.0012(11) -0.0001(11) 0.0062(11) C15 0.0229(14) 0.0222(14) 0.0272(15) -0.0016(12) 0.0054(11) -0.0021(11) C5 0.0275(15) 0.0222(15) 0.0237(14) -0.0027(11) 0.0000(12) 0.0002(11) C21 0.0334(16) 0.0287(16) 0.0245(15) -0.0024(12) -0.0031(12) -0.0018(12) C16 0.0301(15) 0.0249(15) 0.0215(14) -0.0032(11) -0.0007(12) 0.0011(12) C1 0.0191(13) 0.0186(14) 0.0439(18) -0.0022(13) 0.0045(13) 0.0013(11) C37 0.0223(14) 0.0245(14) 0.0180(13) 0.0004(11) 0.0009(11) 0.0018(11) C6 0.0367(17) 0.0266(15) 0.0233(15) 0.0011(12) 0.0096(12) 0.0045(12) C13 0.0233(14) 0.0211(14) 0.0198(13) -0.0002(11) 0.0009(11) 0.0022(11) C41 0.0208(14) 0.0347(16) 0.0202(14) -0.0015(12) -0.0028(11) -0.0007(12) _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 O9 C30 1.272(3) . ? O10 C32 1.329(3) . ? O10 H10A 0.95(4) . ? O4 C11 1.274(3) . ? C32 C31 1.374(4) . ? C32 C33 1.440(4) . ? O3 C9 1.312(3) . ? O3 H3A 0.94(4) . ? C31 C30 1.413(4) . ? C31 H31 0.9500 . ? O6 C18 1.358(3) . ? O6 C20 1.430(3) . ? C18 C19 1.388(4) . ? C18 C17 1.398(4) . ? C30 C29 1.466(4) . ? C10 C9 1.373(4) . ? C10 C11 1.415(4) . ? C10 H10 0.9500 . ? C29 C28 1.331(4) . ? C29 H29 0.9500 . ? O7 C22 1.349(3) . ? O7 H7A 0.85(3) . ? C19 C14 1.407(4) . ? C19 H19 0.9500 . ? C25 C26 1.394(4) . ? C25 C24 1.403(4) . ? C25 C28 1.453(4) . ? C8 C7 1.330(4) . ? C8 C9 1.448(4) . ? C8 H8 0.9500 . ? O11 C38 1.359(3) . ? O11 H11A 0.76(3) . ? C28 H28 0.9500 . ? C14 C15 1.397(4) . ? C14 C13 1.462(4) . ? C4 C3 1.394(4) . ? C4 C5 1.396(4) . ? C4 C7 1.463(4) . ? C24 C23 1.373(4) . ? C24 H24 0.9500 . ? O12 C39 1.368(3) . ? O12 C41 1.441(3) . ? O2 C2 1.381(3) . ? O2 C21 1.435(4) . ? O5 C17 1.365(3) . ? O5 H5A 0.82(3) . ? C35 C36 1.388(4) . ? C35 C40 1.391(4) . ? C35 C34 1.461(4) . ? C2 C3 1.379(4) . ? C2 C1 1.388(4) . ? O1 C1 1.369(3) . ? O1 H1A 1.01(2) . ? C22 C27 1.378(4) . ? C22 C23 1.411(4) . ? C7 H7 0.9500 . ? C34 C33 1.333(4) . ? C34 H34 0.9500 . ? C33 H33 0.9500 . ? C12 C13 1.330(4) . ? C12 C11 1.465(4) . ? C12 H12 0.9500 . ? O8 C23 1.368(3) . ? O8 C42 1.434(3) . ? C40 C39 1.374(4) . ? C40 H40 0.9500 . ? C38 C37 1.387(4) . ? C38 C39 1.398(4) . ? C17 C16 1.374(4) . ? C26 C27 1.391(4) . ? C26 H26 0.9500 . ? C36 C37 1.386(4) . ? C36 H36 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C3 H3 0.9500 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C27 H27 0.9500 . ? C15 C16 1.380(4) . ? C15 H15 0.9500 . ? C5 C6 1.393(4) . ? C5 H5 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C16 H16 0.9500 . ? C1 C6 1.378(4) . ? C37 H37 0.9500 . ? C6 H6 0.9500 . ? C13 H13 0.9500 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? 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 C32 O10 H10A 107(3) . . ? O10 C32 C31 121.6(3) . . ? O10 C32 C33 116.8(2) . . ? C31 C32 C33 121.7(3) . . ? C9 O3 H3A 104(2) . . ? C32 C31 C30 121.7(3) . . ? C32 C31 H31 119.2 . . ? C30 C31 H31 119.2 . . ? C18 O6 C20 116.9(2) . . ? O6 C18 C19 126.6(3) . . ? O6 C18 C17 114.0(2) . . ? C19 C18 C17 119.4(2) . . ? O9 C30 C31 120.8(2) . . ? O9 C30 C29 120.1(2) . . ? C31 C30 C29 119.1(2) . . ? C9 C10 C11 121.4(3) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C28 C29 C30 121.7(3) . . ? C28 C29 H29 119.2 . . ? C30 C29 H29 119.2 . . ? C22 O7 H7A 109(2) . . ? C18 C19 C14 120.9(3) . . ? C18 C19 H19 119.5 . . ? C14 C19 H19 119.5 . . ? C26 C25 C24 118.1(2) . . ? C26 C25 C28 122.9(2) . . ? C24 C25 C28 119.0(2) . . ? C7 C8 C9 123.5(3) . . ? C7 C8 H8 118.3 . . ? C9 C8 H8 118.3 . . ? C38 O11 H11A 113(3) . . ? C29 C28 C25 128.6(3) . . ? C29 C28 H28 115.7 . . ? C25 C28 H28 115.7 . . ? C15 C14 C19 117.9(2) . . ? C15 C14 C13 123.8(2) . . ? C19 C14 C13 118.2(2) . . ? C3 C4 C5 118.4(2) . . ? C3 C4 C7 117.7(3) . . ? C5 C4 C7 123.9(2) . . ? C23 C24 C25 121.9(2) . . ? C23 C24 H24 119.1 . . ? C25 C24 H24 119.1 . . ? C39 O12 C41 116.4(2) . . ? C2 O2 C21 117.3(2) . . ? C17 O5 H5A 105.9(17) . . ? C36 C35 C40 118.5(2) . . ? C36 C35 C34 123.1(2) . . ? C40 C35 C34 118.4(2) . . ? C3 C2 O2 125.4(3) . . ? C3 C2 C1 119.4(3) . . ? O2 C2 C1 115.2(2) . . ? C1 O1 H1A 102(3) . . ? O7 C22 C27 124.4(2) . . ? O7 C22 C23 116.8(2) . . ? C27 C22 C23 118.7(2) . . ? C8 C7 C4 127.9(3) . . ? C8 C7 H7 116.0 . . ? C4 C7 H7 116.0 . . ? C33 C34 C35 126.8(2) . . ? C33 C34 H34 116.6 . . ? C35 C34 H34 116.6 . . ? C34 C33 C32 124.0(3) . . ? C34 C33 H33 118.0 . . ? C32 C33 H33 118.0 . . ? C13 C12 C11 121.5(3) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C23 O8 C42 115.7(2) . . ? C39 C40 C35 121.5(2) . . ? C39 C40 H40 119.2 . . ? C35 C40 H40 119.2 . . ? O11 C38 C37 118.5(2) . . ? O11 C38 C39 122.3(2) . . ? C37 C38 C39 119.2(2) . . ? O5 C17 C16 119.2(2) . . ? O5 C17 C18 120.6(2) . . ? C16 C17 C18 120.2(2) . . ? C27 C26 C25 120.1(3) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C37 C36 C35 120.6(2) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? O8 C23 C24 125.4(2) . . ? O8 C23 C22 115.0(2) . . ? C24 C23 C22 119.6(2) . . ? O6 C20 H20A 109.5 . . ? O6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C2 C3 C4 121.5(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? O4 C11 C10 120.6(3) . . ? O4 C11 C12 119.5(2) . . ? C10 C11 C12 120.0(2) . . ? O12 C39 C40 124.9(2) . . ? O12 C39 C38 115.3(2) . . ? C40 C39 C38 119.8(2) . . ? O8 C42 H42A 109.5 . . ? O8 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? O8 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C22 C27 C26 121.6(3) . . ? C22 C27 H27 119.2 . . ? C26 C27 H27 119.2 . . ? O3 C9 C10 120.9(3) . . ? O3 C9 C8 116.9(2) . . ? C10 C9 C8 122.1(2) . . ? C16 C15 C14 121.2(3) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? O1 C1 C6 120.1(3) . . ? O1 C1 C2 119.7(3) . . ? C6 C1 C2 120.2(3) . . ? C36 C37 C38 120.4(2) . . ? C36 C37 H37 119.8 . . ? C38 C37 H37 119.8 . . ? C1 C6 C5 120.3(3) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C12 C13 C14 127.7(3) . . ? C12 C13 H13 116.2 . . ? C14 C13 H13 116.2 . . ? O12 C41 H41A 109.5 . . ? O12 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O12 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.583 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.057 # Attachment '- Form3-pbca.cif' data_Form3_Pbca _database_code_depnum_ccdc_archive 'CCDC 807906' #TrackingRef '- Form3-pbca.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 O6' _chemical_formula_weight 368.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.536(3) _cell_length_b 7.9916(17) _cell_length_c 34.462(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3452.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 869 _cell_measurement_theta_min 2.8033 _cell_measurement_theta_max 26.3135 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8888 _diffrn_reflns_av_R_equivalents 0.1808 _diffrn_reflns_av_sigmaI/netI 0.2958 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 26.36 _reflns_number_total 3510 _reflns_number_gt 1127 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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. ; _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^)+(0.0000P)^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 3510 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2681 _refine_ls_R_factor_gt 0.0893 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _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 O4 O 0.6571(4) 0.2302(6) 0.64649(14) 0.0286(12) Uani 1 1 d . . . O3 O 0.6623(3) 0.3956(5) 0.58529(12) 0.0244(11) Uani 1 1 d . . . O1 O 0.9676(3) 0.9702(5) 0.41337(13) 0.0281(11) Uani 1 1 d . . . O6 O 0.6918(3) -0.2045(5) 0.83121(14) 0.0390(13) Uani 1 1 d . . . C4 C 0.8348(5) 0.6580(7) 0.49723(17) 0.0218(15) Uani 1 1 d . . . O5 O 0.9019(4) -0.2445(6) 0.84309(14) 0.0324(12) Uani 1 1 d . . . C3 C 0.7758(5) 0.7192(6) 0.46577(16) 0.0196(14) Uani 1 1 d . . . H3 H 0.7041 0.6910 0.4637 0.024 Uiso 1 1 calc R . . C2 C 0.8207(5) 0.8190(7) 0.43807(18) 0.0206(15) Uani 1 1 d . . . C10 C 0.8184(5) 0.3143(7) 0.61814(17) 0.0219(15) Uani 1 1 d . . . H10 H 0.8925 0.3134 0.6186 0.026 Uiso 1 1 calc R . . O2 O 0.7693(3) 0.8867(5) 0.40663(12) 0.0291(11) Uani 1 1 d . . . C8 C 0.8261(4) 0.4918(6) 0.55893(16) 0.0186(14) Uani 1 1 d . . . H8 H 0.8984 0.5077 0.5637 0.022 Uiso 1 1 calc R . . C11 C 0.7635(5) 0.2354(7) 0.64670(18) 0.0203(15) Uani 1 1 d . . . C7 C 0.7852(5) 0.5548(6) 0.52663(17) 0.0202(15) Uani 1 1 d . . . H7 H 0.7139 0.5288 0.5222 0.024 Uiso 1 1 calc R . . C12 C 0.8149(5) 0.1520(7) 0.67965(16) 0.0192(15) Uani 1 1 d . . . H12 H 0.8888 0.1402 0.6796 0.023 Uiso 1 1 calc R . . C9 C 0.7640(5) 0.3991(7) 0.58733(18) 0.0203(15) Uani 1 1 d . . . C14 C 0.7992(5) 0.0110(7) 0.74451(18) 0.0229(15) Uani 1 1 d . . . C13 C 0.7596(5) 0.0926(7) 0.70957(17) 0.0201(15) Uani 1 1 d . . . H13 H 0.6860 0.1048 0.7080 0.024 Uiso 1 1 calc R . . C15 C 0.9073(5) -0.0121(7) 0.75159(19) 0.0230(16) Uani 1 1 d . . . H15 H 0.9577 0.0284 0.7342 0.028 Uiso 1 1 calc R . . C17 C 0.8671(5) -0.1592(7) 0.81089(18) 0.0250(16) Uani 1 1 d . . . C5 C 0.9429(5) 0.7039(7) 0.49932(19) 0.0264(17) Uani 1 1 d . . . H5 H 0.9848 0.6646 0.5196 0.032 Uiso 1 1 calc R . . C1 C 0.9284(5) 0.8678(7) 0.44070(19) 0.0223(15) Uani 1 1 d . . . C6 C 0.9869(5) 0.8056(7) 0.4718(2) 0.0291(17) Uani 1 1 d . . . H6 H 1.0586 0.8343 0.4739 0.035 Uiso 1 1 calc R . . C21 C 0.6538(4) 0.8785(8) 0.4076(2) 0.0363(18) Uani 1 1 d . . . H21A H 0.6316 0.7635 0.4071 0.054 Uiso 1 1 calc R . . H21B H 0.6252 0.9357 0.3854 0.054 Uiso 1 1 calc R . . H21C H 0.6282 0.9308 0.4309 0.054 Uiso 1 1 calc R . . C19 C 0.7257(5) -0.0513(7) 0.77126(18) 0.0240(16) Uani 1 1 d . . . H19 H 0.6532 -0.0351 0.7670 0.029 Uiso 1 1 calc R . . C18 C 0.7584(5) -0.1356(7) 0.80364(18) 0.0215(15) Uani 1 1 d . . . C20 C 0.5784(4) -0.1790(8) 0.8253(2) 0.040(2) Uani 1 1 d . . . H20A H 0.5618 -0.0624 0.8284 0.060 Uiso 1 1 calc R . . H20B H 0.5391 -0.2432 0.8440 0.060 Uiso 1 1 calc R . . H20C H 0.5593 -0.2144 0.7996 0.060 Uiso 1 1 calc R . . C16 C 0.9403(5) -0.0975(7) 0.78542(19) 0.0286(17) Uani 1 1 d . . . H16 H 1.0126 -0.1118 0.7903 0.034 Uiso 1 1 calc R . . H4A H 0.638(5) 0.290(7) 0.628(2) 0.05(2) Uiso 1 1 d . . . H1 H 1.039(4) 1.017(6) 0.4176(17) 0.027(18) Uiso 1 1 d . . . H5A H 0.843(5) -0.263(10) 0.853(3) 0.09(4) 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 O4 0.028(3) 0.028(3) 0.029(3) 0.011(2) -0.003(3) -0.001(2) O3 0.022(2) 0.024(2) 0.028(3) 0.004(2) -0.002(2) 0.007(2) O1 0.027(3) 0.028(3) 0.029(3) 0.013(2) 0.000(3) -0.009(2) O6 0.033(3) 0.051(3) 0.033(3) 0.015(3) 0.003(3) -0.001(3) C4 0.032(4) 0.023(3) 0.011(3) -0.002(3) 0.007(3) 0.004(3) O5 0.030(3) 0.044(3) 0.023(3) 0.010(2) 0.004(3) 0.002(3) C3 0.022(3) 0.021(3) 0.016(3) -0.002(3) 0.001(3) -0.005(3) C2 0.026(4) 0.024(4) 0.012(3) 0.000(3) -0.003(3) 0.007(3) C10 0.025(4) 0.021(3) 0.020(3) 0.004(3) -0.004(3) 0.003(3) O2 0.026(3) 0.043(3) 0.018(3) 0.005(2) 0.002(2) -0.003(2) C8 0.024(4) 0.018(3) 0.014(3) 0.002(3) 0.001(3) -0.001(3) C11 0.026(4) 0.016(3) 0.019(4) -0.003(3) -0.002(3) -0.002(3) C7 0.024(4) 0.013(3) 0.024(4) 0.000(3) -0.002(3) 0.006(3) C12 0.021(3) 0.020(3) 0.016(3) -0.008(3) -0.002(3) -0.002(3) C9 0.038(4) 0.009(3) 0.013(3) -0.005(3) 0.002(3) 0.002(3) C14 0.027(4) 0.021(4) 0.020(4) -0.002(3) 0.006(3) -0.006(3) C13 0.014(3) 0.025(3) 0.022(4) -0.001(3) -0.007(3) 0.000(3) C15 0.022(4) 0.027(4) 0.020(4) 0.002(3) -0.002(3) -0.005(3) C17 0.041(4) 0.019(4) 0.015(3) 0.001(3) -0.008(4) -0.002(3) C5 0.031(4) 0.023(4) 0.026(4) 0.009(3) -0.003(4) 0.002(3) C1 0.024(4) 0.021(4) 0.022(4) -0.011(3) 0.003(3) -0.005(3) C6 0.021(4) 0.033(4) 0.034(4) 0.001(3) -0.011(4) -0.008(3) C21 0.023(4) 0.045(4) 0.041(4) -0.003(4) -0.005(4) -0.002(4) C19 0.026(4) 0.022(4) 0.024(4) -0.010(3) -0.001(4) -0.004(3) C18 0.024(4) 0.023(4) 0.018(4) 0.003(3) 0.007(3) -0.005(3) C20 0.026(4) 0.069(5) 0.025(4) 0.014(4) 0.007(4) -0.002(4) C16 0.024(4) 0.026(4) 0.037(4) 0.003(3) 0.004(4) 0.007(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 O4 C11 1.334(7) . ? O4 H4A 0.84(6) . ? O3 C9 1.277(6) . ? O1 C1 1.341(7) . ? O1 H1 0.98(5) . ? O6 C18 1.379(7) . ? O6 C20 1.450(6) . ? C4 C3 1.400(8) . ? C4 C5 1.406(8) . ? C4 C7 1.447(8) . ? O5 C17 1.374(7) . ? O5 H5A 0.83(7) . ? C3 C2 1.365(8) . ? C3 H3 0.9300 . ? C2 O2 1.371(7) . ? C2 C1 1.408(7) . ? C10 C11 1.356(8) . ? C10 C9 1.432(8) . ? C10 H10 0.9300 . ? O2 C21 1.450(6) . ? C8 C7 1.325(7) . ? C8 C9 1.454(7) . ? C8 H8 0.9300 . ? C11 C12 1.466(8) . ? C7 H7 0.9300 . ? C12 C13 1.330(7) . ? C12 H12 0.9300 . ? C14 C15 1.389(8) . ? C14 C19 1.395(8) . ? C14 C13 1.456(8) . ? C13 H13 0.9300 . ? C15 C16 1.413(8) . ? C15 H15 0.9300 . ? C17 C16 1.362(8) . ? C17 C18 1.398(8) . ? C5 C6 1.366(8) . ? C5 H5 0.9300 . ? C1 C6 1.390(8) . ? C6 H6 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C19 C18 1.366(8) . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C16 H16 0.9300 . ? 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 C11 O4 H4A 106(5) . . ? C1 O1 H1 118(3) . . ? C18 O6 C20 116.1(5) . . ? C3 C4 C5 117.2(6) . . ? C3 C4 C7 121.0(6) . . ? C5 C4 C7 121.8(6) . . ? C17 O5 H5A 98(6) . . ? C2 C3 C4 121.9(6) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C3 C2 O2 126.1(5) . . ? C3 C2 C1 120.8(6) . . ? O2 C2 C1 113.0(6) . . ? C11 C10 C9 121.1(6) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C2 O2 C21 115.6(5) . . ? C7 C8 C9 123.5(6) . . ? C7 C8 H8 118.3 . . ? C9 C8 H8 118.3 . . ? O4 C11 C10 121.1(6) . . ? O4 C11 C12 115.4(6) . . ? C10 C11 C12 123.4(6) . . ? C8 C7 C4 129.7(6) . . ? C8 C7 H7 115.2 . . ? C4 C7 H7 115.2 . . ? C13 C12 C11 122.2(6) . . ? C13 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? O3 C9 C10 120.4(6) . . ? O3 C9 C8 120.6(6) . . ? C10 C9 C8 119.1(5) . . ? C15 C14 C19 118.7(6) . . ? C15 C14 C13 122.5(6) . . ? C19 C14 C13 118.8(6) . . ? C12 C13 C14 128.5(6) . . ? C12 C13 H13 115.7 . . ? C14 C13 H13 115.7 . . ? C14 C15 C16 119.6(6) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C16 C17 O5 119.1(6) . . ? C16 C17 C18 119.5(6) . . ? O5 C17 C18 121.4(6) . . ? C6 C5 C4 120.6(6) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? O1 C1 C6 124.5(6) . . ? O1 C1 C2 118.4(6) . . ? C6 C1 C2 117.2(6) . . ? C5 C6 C1 122.3(6) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C19 C14 121.2(6) . . ? C18 C19 H19 119.4 . . ? C14 C19 H19 119.4 . . ? C19 C18 O6 125.3(6) . . ? C19 C18 C17 120.3(6) . . ? O6 C18 C17 114.4(6) . . ? O6 C20 H20A 109.5 . . ? O6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C16 C15 120.6(6) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.279 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.074