Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jubaraj B. Baruah' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology North Guwahati 780 031 INDIA ; _publ_contact_author_email JUBA@IITG.ERNET.IN _publ_section_title ; Selectivity in guest-host binding in assemblies of bis-phenols ; loop_ _publ_author_name 'B. Baruah' 'Rupam J. Sarma' # Attachment 'D4OMe.cif' data_dmp-2 _database_code_depnum_ccdc_archive 'CCDC 204519' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 O3' _chemical_formula_sum 'C24 H26 O3' _chemical_formula_weight 362.45 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.771(3) _cell_length_b 10.467(6) _cell_length_c 11.703(7) _cell_angle_alpha 99.62(3) _cell_angle_beta 101.62(4) _cell_angle_gamma 117.14(3) _cell_volume 996.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.078 _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 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 'STOE STUDI4' _diffrn_measurement_method Omega/2Theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60min _diffrn_standards_decay_% 8 _diffrn_reflns_number 3515 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3515 _reflns_number_gt 2676 _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^)+(0.0631P)^2^+0.8290P] 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 0.025(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3515 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1406 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.007 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 1.3063(3) -0.3555(3) -0.0490(2) 0.0666(6) Uani 1 1 d . . . O2 O 0.5180(3) -0.2241(2) -0.53884(16) 0.0575(5) Uani 1 1 d . . . O3 O 0.6996(2) -0.01003(19) 0.33257(15) 0.0534(5) Uani 1 1 d . . . C1 C 0.7212(3) -0.3418(2) -0.09651(19) 0.0328(5) Uani 1 1 d . . . C2 C 0.7158(2) -0.2477(2) 0.01522(18) 0.0313(5) Uani 1 1 d . . . C3 C 0.7502(3) -0.1012(3) 0.0308(2) 0.0406(5) Uani 1 1 d . . . C4 C 0.7473(3) -0.0172(3) 0.1349(2) 0.0432(6) Uani 1 1 d . . . C5 C 0.7078(3) -0.0812(3) 0.2257(2) 0.0377(5) Uani 1 1 d . . . C6 C 0.6712(3) -0.2288(3) 0.2120(2) 0.0412(6) Uani 1 1 d . . . C7 C 0.6766(3) -0.3097(3) 0.1085(2) 0.0359(5) Uani 1 1 d . . . C8 C 0.8825(3) -0.3399(2) -0.07754(19) 0.0332(5) Uani 1 1 d . . . C9 C 1.0177(3) -0.2476(3) 0.0237(2) 0.0371(5) Uani 1 1 d . . . C10 C 1.1619(3) -0.2497(3) 0.0381(2) 0.0434(6) Uani 1 1 d . . . C11 C 1.1679(3) -0.3474(3) -0.0543(2) 0.0456(6) Uani 1 1 d . . . C12 C 1.0339(3) -0.4437(3) -0.1572(2) 0.0459(6) Uani 1 1 d . . . C13 C 0.8921(3) -0.4390(3) -0.1670(2) 0.0425(6) Uani 1 1 d . . . C14 C 0.6723(3) -0.3058(2) -0.21413(19) 0.0330(5) Uani 1 1 d . . . C15 C 0.7819(3) -0.1899(3) -0.2482(2) 0.0374(5) Uani 1 1 d . . . C16 C 0.7359(3) -0.1571(3) -0.3551(2) 0.0396(5) Uani 1 1 d . . . C17 C 0.5750(3) -0.2465(3) -0.43024(19) 0.0392(5) Uani 1 1 d . . . C18 C 0.4621(3) -0.3671(3) -0.40159(19) 0.0376(5) Uani 1 1 d . . . C19 C 0.5135(3) -0.3922(3) -0.2922(2) 0.0351(5) Uani 1 1 d . . . C20 C 1.3071(4) -0.1483(4) 0.1498(4) 0.0690(9) Uani 1 1 d . . . C21 C 1.0418(6) -0.5514(5) -0.2552(3) 0.0729(10) Uani 1 1 d . . . C22 C 0.8579(4) -0.0296(4) -0.3888(3) 0.0665(9) Uani 1 1 d . . . C23 C 0.2922(3) -0.4704(4) -0.4880(3) 0.0508(7) Uani 1 1 d . . . C24 C 0.7422(6) 0.1433(4) 0.3536(4) 0.0797(11) Uani 1 1 d . . . H1O H 1.395(6) -0.277(5) 0.015(4) 0.140(19) Uiso 1 1 d . . . H2O H 0.602(4) -0.147(4) -0.551(3) 0.081(11) Uiso 1 1 d . . . H1A H 0.638(3) -0.448(2) -0.1084(18) 0.029(5) Uiso 1 1 d . . . H3A H 0.781(3) -0.054(3) -0.032(2) 0.046(7) Uiso 1 1 d . . . H4A H 0.775(3) 0.085(3) 0.143(2) 0.054(7) Uiso 1 1 d . . . H6A H 0.643(3) -0.274(3) 0.276(2) 0.048(7) Uiso 1 1 d . . . H7A H 0.655(3) -0.412(3) 0.100(2) 0.041(6) Uiso 1 1 d . . . H9A H 1.014(3) -0.177(3) 0.087(2) 0.038(6) Uiso 1 1 d . . . H13A H 0.793(3) -0.511(3) -0.241(2) 0.054(7) Uiso 1 1 d . . . H15A H 0.893(3) -0.129(3) -0.198(2) 0.035(6) Uiso 1 1 d . . . H19A H 0.432(3) -0.475(3) -0.2714(19) 0.033(6) Uiso 1 1 d . . . H20A H 1.406(5) -0.082(4) 0.130(3) 0.108(13) Uiso 1 1 d . . . H20B H 1.342(4) -0.204(4) 0.194(3) 0.086(11) Uiso 1 1 d . . . H20C H 1.289(5) -0.075(5) 0.208(4) 0.113(13) Uiso 1 1 d . . . H21A H 0.936(5) -0.610(5) -0.322(4) 0.111(14) Uiso 1 1 d . . . H21B H 1.065(6) -0.620(5) -0.227(4) 0.140(18) Uiso 1 1 d . . . H21C H 1.120(6) -0.498(5) -0.292(4) 0.138(18) Uiso 1 1 d . . . H22A H 0.864(4) -0.067(4) -0.470(4) 0.099(12) Uiso 1 1 d . . . H22B H 0.963(5) 0.019(4) -0.327(3) 0.094(11) Uiso 1 1 d . . . H22C H 0.824(6) 0.041(6) -0.404(4) 0.149(19) Uiso 1 1 d . . . H23A H 0.291(4) -0.525(3) -0.567(3) 0.076(9) Uiso 1 1 d . . . H23B H 0.224(4) -0.550(4) -0.456(3) 0.094(12) Uiso 1 1 d . . . H23C H 0.235(4) -0.419(4) -0.507(3) 0.095(12) Uiso 1 1 d . . . H24A H 0.863(5) 0.202(4) 0.359(3) 0.083(11) Uiso 1 1 d . . . H24B H 0.676(5) 0.156(5) 0.283(4) 0.120(15) Uiso 1 1 d . . . H24C H 0.732(4) 0.176(4) 0.431(4) 0.097(12) 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 0.0512(12) 0.0765(14) 0.0954(16) 0.0277(13) 0.0324(12) 0.0461(12) O2 0.0599(12) 0.0770(14) 0.0380(10) 0.0286(9) 0.0120(9) 0.0341(11) O3 0.0817(13) 0.0495(10) 0.0385(9) 0.0108(8) 0.0239(9) 0.0397(10) C1 0.0336(11) 0.0345(12) 0.0327(11) 0.0131(9) 0.0124(9) 0.0174(10) C2 0.0278(11) 0.0366(11) 0.0323(11) 0.0131(9) 0.0098(9) 0.0176(9) C3 0.0505(14) 0.0410(13) 0.0402(13) 0.0199(11) 0.0224(11) 0.0252(11) C4 0.0548(15) 0.0364(13) 0.0459(14) 0.0162(11) 0.0191(11) 0.0263(12) C5 0.0398(12) 0.0428(13) 0.0335(11) 0.0083(10) 0.0117(10) 0.0242(11) C6 0.0528(15) 0.0452(13) 0.0373(12) 0.0203(11) 0.0221(11) 0.0281(12) C7 0.0419(12) 0.0363(12) 0.0372(12) 0.0158(10) 0.0155(10) 0.0232(10) C8 0.0385(12) 0.0374(12) 0.0342(11) 0.0180(9) 0.0159(9) 0.0233(10) C9 0.0383(13) 0.0377(12) 0.0420(13) 0.0147(10) 0.0157(10) 0.0224(10) C10 0.0378(13) 0.0432(13) 0.0552(15) 0.0196(11) 0.0143(11) 0.0237(11) C11 0.0465(14) 0.0553(15) 0.0602(16) 0.0318(13) 0.0282(13) 0.0363(13) C12 0.0623(16) 0.0601(15) 0.0444(14) 0.0272(12) 0.0285(12) 0.0453(14) C13 0.0542(15) 0.0528(14) 0.0348(12) 0.0171(11) 0.0155(11) 0.0365(13) C14 0.0346(11) 0.0383(11) 0.0322(11) 0.0104(9) 0.0135(9) 0.0222(10) C15 0.0322(12) 0.0436(13) 0.0356(12) 0.0124(10) 0.0104(10) 0.0186(11) C16 0.0439(13) 0.0452(13) 0.0361(12) 0.0182(10) 0.0176(10) 0.0238(11) C17 0.0478(14) 0.0521(14) 0.0278(11) 0.0136(10) 0.0140(10) 0.0319(12) C18 0.0376(12) 0.0438(13) 0.0338(12) 0.0069(10) 0.0107(10) 0.0243(11) C19 0.0357(12) 0.0382(12) 0.0364(12) 0.0125(10) 0.0144(10) 0.0209(10) C20 0.0441(17) 0.068(2) 0.083(2) 0.0063(18) 0.0019(16) 0.0319(16) C21 0.102(3) 0.105(3) 0.0528(19) 0.0213(19) 0.032(2) 0.083(3) C22 0.0567(19) 0.076(2) 0.0559(19) 0.0380(17) 0.0183(15) 0.0187(17) C23 0.0407(14) 0.0640(18) 0.0394(14) 0.0071(13) 0.0058(11) 0.0256(14) C24 0.130(4) 0.059(2) 0.063(2) 0.0113(17) 0.036(2) 0.058(2) _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 C11 1.382(3) . ? O1 H1O 0.93(5) . ? O2 C17 1.384(3) . ? O2 H2O 0.91(4) . ? O3 C5 1.381(3) . ? O3 C24 1.424(4) . ? C1 C2 1.526(3) . ? C1 C14 1.529(3) . ? C1 C8 1.537(3) . ? C1 H1A 1.00(2) . ? C2 C3 1.382(3) . ? C2 C7 1.392(3) . ? C3 C4 1.392(3) . ? C3 H3A 0.97(3) . ? C4 C5 1.377(3) . ? C4 H4A 0.96(3) . ? C5 C6 1.390(3) . ? C6 C7 1.382(3) . ? C6 H6A 0.97(3) . ? C7 H7A 0.97(2) . ? C8 C9 1.380(3) . ? C8 C13 1.394(3) . ? C9 C10 1.395(3) . ? C9 H9A 0.98(2) . ? C10 C11 1.390(3) . ? C10 C20 1.505(4) . ? C11 C12 1.391(4) . ? C12 C13 1.392(3) . ? C12 C21 1.509(4) . ? C13 H13A 1.02(3) . ? C14 C15 1.388(3) . ? C14 C19 1.390(3) . ? C15 C16 1.394(3) . ? C15 H15A 0.96(2) . ? C16 C17 1.395(3) . ? C16 C22 1.508(4) . ? C17 C18 1.394(3) . ? C18 C19 1.391(3) . ? C18 C23 1.506(4) . ? C19 H19A 0.98(2) . ? C20 H20A 1.00(4) . ? C20 H20B 0.97(4) . ? C20 H20C 1.04(4) . ? C21 H21A 0.99(4) . ? C21 H21B 0.93(5) . ? C21 H21C 0.95(5) . ? C22 H22A 0.99(4) . ? C22 H22B 0.97(4) . ? C22 H22C 0.96(5) . ? C23 H23A 1.00(3) . ? C23 H23B 0.99(4) . ? C23 H23C 0.96(4) . ? C24 H24A 1.03(4) . ? C24 H24B 1.01(4) . ? C24 H24C 0.96(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 H1O 111(3) . . ? C17 O2 H2O 108(2) . . ? C5 O3 C24 117.9(2) . . ? C2 C1 C14 113.34(17) . . ? C2 C1 C8 113.49(18) . . ? C14 C1 C8 111.70(17) . . ? C2 C1 H1A 106.0(12) . . ? C14 C1 H1A 106.3(12) . . ? C8 C1 H1A 105.2(12) . . ? C3 C2 C7 117.1(2) . . ? C3 C2 C1 123.57(19) . . ? C7 C2 C1 119.30(19) . . ? C2 C3 C4 122.3(2) . . ? C2 C3 H3A 119.0(14) . . ? C4 C3 H3A 118.7(14) . . ? C5 C4 C3 119.5(2) . . ? C5 C4 H4A 120.8(16) . . ? C3 C4 H4A 119.7(16) . . ? C4 C5 O3 124.9(2) . . ? C4 C5 C6 119.5(2) . . ? O3 C5 C6 115.6(2) . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6A 120.5(14) . . ? C5 C6 H6A 119.4(14) . . ? C6 C7 C2 121.6(2) . . ? C6 C7 H7A 120.6(14) . . ? C2 C7 H7A 117.8(14) . . ? C9 C8 C13 118.1(2) . . ? C9 C8 C1 123.86(19) . . ? C13 C8 C1 118.1(2) . . ? C8 C9 C10 122.2(2) . . ? C8 C9 H9A 119.4(13) . . ? C10 C9 H9A 118.4(13) . . ? C11 C10 C9 118.0(2) . . ? C11 C10 C20 120.9(2) . . ? C9 C10 C20 121.1(2) . . ? O1 C11 C10 122.1(2) . . ? O1 C11 C12 116.3(2) . . ? C10 C11 C12 121.6(2) . . ? C13 C12 C11 118.4(2) . . ? C13 C12 C21 120.9(3) . . ? C11 C12 C21 120.7(3) . . ? C12 C13 C8 121.7(2) . . ? C12 C13 H13A 118.7(15) . . ? C8 C13 H13A 119.5(15) . . ? C15 C14 C19 117.7(2) . . ? C15 C14 C1 122.4(2) . . ? C19 C14 C1 119.9(2) . . ? C14 C15 C16 122.0(2) . . ? C14 C15 H15A 120.4(13) . . ? C16 C15 H15A 117.7(13) . . ? C15 C16 C17 118.2(2) . . ? C15 C16 C22 120.6(2) . . ? C17 C16 C22 121.2(2) . . ? O2 C17 C16 122.6(2) . . ? O2 C17 C18 115.7(2) . . ? C16 C17 C18 121.7(2) . . ? C19 C18 C17 117.6(2) . . ? C19 C18 C23 121.0(2) . . ? C17 C18 C23 121.3(2) . . ? C14 C19 C18 122.7(2) . . ? C14 C19 H19A 120.3(13) . . ? C18 C19 H19A 117.0(13) . . ? C10 C20 H20A 113(2) . . ? C10 C20 H20B 112(2) . . ? H20A C20 H20B 103(3) . . ? C10 C20 H20C 113(2) . . ? H20A C20 H20C 105(3) . . ? H20B C20 H20C 111(3) . . ? C12 C21 H21A 110(2) . . ? C12 C21 H21B 114(3) . . ? H21A C21 H21B 107(4) . . ? C12 C21 H21C 111(3) . . ? H21A C21 H21C 106(4) . . ? H21B C21 H21C 109(4) . . ? C16 C22 H22A 110(2) . . ? C16 C22 H22B 110(2) . . ? H22A C22 H22B 111(3) . . ? C16 C22 H22C 113(3) . . ? H22A C22 H22C 101(4) . . ? H22B C22 H22C 112(4) . . ? C18 C23 H23A 111.6(18) . . ? C18 C23 H23B 113(2) . . ? H23A C23 H23B 105(3) . . ? C18 C23 H23C 113(2) . . ? H23A C23 H23C 108(3) . . ? H23B C23 H23C 106(3) . . ? O3 C24 H24A 106.3(19) . . ? O3 C24 H24B 110(2) . . ? H24A C24 H24B 109(3) . . ? O3 C24 H24C 108(2) . . ? H24A C24 H24C 109(3) . . ? H24B C24 H24C 115(3) . . ? 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 C14 C1 C2 C3 -32.9(3) . . . . ? C8 C1 C2 C3 95.9(2) . . . . ? C14 C1 C2 C7 148.1(2) . . . . ? C8 C1 C2 C7 -83.2(2) . . . . ? C7 C2 C3 C4 0.4(3) . . . . ? C1 C2 C3 C4 -178.7(2) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C3 C4 C5 O3 -179.5(2) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C24 O3 C5 C4 -3.1(4) . . . . ? C24 O3 C5 C6 177.5(3) . . . . ? C4 C5 C6 C7 0.8(4) . . . . ? O3 C5 C6 C7 -179.7(2) . . . . ? C5 C6 C7 C2 -1.0(4) . . . . ? C3 C2 C7 C6 0.4(3) . . . . ? C1 C2 C7 C6 179.5(2) . . . . ? C2 C1 C8 C9 -8.1(3) . . . . ? C14 C1 C8 C9 121.5(2) . . . . ? C2 C1 C8 C13 170.85(19) . . . . ? C14 C1 C8 C13 -59.5(3) . . . . ? C13 C8 C9 C10 0.6(3) . . . . ? C1 C8 C9 C10 179.6(2) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C8 C9 C10 C20 -179.7(3) . . . . ? C9 C10 C11 O1 178.9(2) . . . . ? C20 C10 C11 O1 -0.6(4) . . . . ? C9 C10 C11 C12 -1.6(3) . . . . ? C20 C10 C11 C12 178.9(3) . . . . ? O1 C11 C12 C13 -179.7(2) . . . . ? C10 C11 C12 C13 0.8(4) . . . . ? O1 C11 C12 C21 0.9(4) . . . . ? C10 C11 C12 C21 -178.6(3) . . . . ? C11 C12 C13 C8 0.7(3) . . . . ? C21 C12 C13 C8 -179.8(3) . . . . ? C9 C8 C13 C12 -1.4(3) . . . . ? C1 C8 C13 C12 179.5(2) . . . . ? C2 C1 C14 C15 85.5(2) . . . . ? C8 C1 C14 C15 -44.2(3) . . . . ? C2 C1 C14 C19 -95.5(2) . . . . ? C8 C1 C14 C19 134.8(2) . . . . ? C19 C14 C15 C16 1.5(3) . . . . ? C1 C14 C15 C16 -179.5(2) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C14 C15 C16 C22 179.5(3) . . . . ? C15 C16 C17 O2 -179.3(2) . . . . ? C22 C16 C17 O2 -0.1(4) . . . . ? C15 C16 C17 C18 -0.9(3) . . . . ? C22 C16 C17 C18 178.3(3) . . . . ? O2 C17 C18 C19 -178.92(19) . . . . ? C16 C17 C18 C19 2.6(3) . . . . ? O2 C17 C18 C23 3.4(3) . . . . ? C16 C17 C18 C23 -175.1(2) . . . . ? C15 C14 C19 C18 0.3(3) . . . . ? C1 C14 C19 C18 -178.73(19) . . . . ? C17 C18 C19 C14 -2.3(3) . . . . ? C23 C18 C19 C14 175.4(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.171 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.034 # Attachment 'D4CHO.cif' data_rj42 _database_code_depnum_ccdc_archive 'CCDC 281627' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;Bis(4-hydroxy-3,5-dimethylphenyl)(4-formylphenyl)methane: benzene inclusion ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H30 O3' _chemical_formula_sum 'C30 H30 O3' _chemical_formula_weight 438.54 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(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.007(6) _cell_length_b 9.772(5) _cell_length_c 21.546(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.194(3) _cell_angle_gamma 90.00 _cell_volume 2502.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7013 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description prisms _exptl_crystal_colour orange _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.07 _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 0.71073 _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 29763 _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 30.56 _reflns_number_total 7529 _reflns_number_gt 3996 _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^)+(0.1236P)^2^+0.4613P] 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 0.0006(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7529 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1301 _refine_ls_R_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.2459 _refine_ls_wR_factor_gt 0.1912 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 0.04954(12) 0.86963(18) 0.35374(8) 0.0602(4) Uani 1 1 d . . . O2 O 0.84961(14) 1.0161(2) 0.38343(8) 0.0737(5) Uani 1 1 d . . . H1O H 0.072(3) 0.829(3) 0.3893(16) 0.089(9) Uiso 1 1 d . . . H2O H 0.899(4) 0.959(5) 0.373(2) 0.155(17) Uiso 1 1 d . . . O3 O 0.52561(19) 0.7318(2) -0.03032(9) 0.0970(7) Uani 1 1 d . . . C1 C 0.14277(14) 0.89920(19) 0.32577(8) 0.0432(4) Uani 1 1 d . . . C2 C 0.12345(15) 0.97309(19) 0.26981(9) 0.0446(4) Uani 1 1 d . . . C3 C 0.21594(15) 1.00772(19) 0.24098(8) 0.0440(4) Uani 1 1 d . . . C4 C 0.32539(15) 0.97120(18) 0.26588(8) 0.0406(4) Uani 1 1 d . . . C5 C 0.34029(16) 0.8964(2) 0.32104(9) 0.0448(4) Uani 1 1 d . . . C6 C 0.25024(15) 0.8601(2) 0.35214(9) 0.0461(4) Uani 1 1 d . . . C7 C 0.42214(15) 1.01174(19) 0.23099(8) 0.0426(4) Uani 1 1 d . . . C8 C 0.53673(15) 1.00901(19) 0.27187(8) 0.0434(4) Uani 1 1 d . . . C9 C 0.57247(17) 1.1202(2) 0.30985(9) 0.0490(5) Uani 1 1 d . . . C10 C 0.67685(17) 1.1229(2) 0.34716(10) 0.0549(5) Uani 1 1 d . . . C11 C 0.74734(16) 1.0094(2) 0.34628(9) 0.0526(5) Uani 1 1 d . . . C12 C 0.71299(16) 0.8947(2) 0.31030(9) 0.0508(5) Uani 1 1 d . . . C13 C 0.60868(16) 0.8974(2) 0.27289(9) 0.0480(4) Uani 1 1 d . . . C14 C 0.42559(15) 0.92981(19) 0.17110(8) 0.0428(4) Uani 1 1 d . . . C15 C 0.37441(18) 0.8041(2) 0.16012(9) 0.0524(5) Uani 1 1 d . . . C16 C 0.3876(2) 0.7294(2) 0.10721(10) 0.0579(5) Uani 1 1 d . . . C17 C 0.45273(18) 0.7796(2) 0.06402(9) 0.0540(5) Uani 1 1 d . . . C18 C 0.50347(18) 0.9064(3) 0.07432(9) 0.0572(5) Uani 1 1 d . . . C19 C 0.48972(18) 0.9809(2) 0.12683(9) 0.0527(5) Uani 1 1 d . . . C20 C 0.00665(17) 1.0162(3) 0.24243(11) 0.0625(6) Uani 1 1 d . . . H20A H 0.0103 1.0739 0.2067 0.094 Uiso 1 1 calc R . . H20B H -0.0273 1.0657 0.2734 0.094 Uiso 1 1 calc R . . H20C H -0.0377 0.9366 0.2297 0.094 Uiso 1 1 calc R . . C21 C 0.2694(2) 0.7801(3) 0.41249(11) 0.0730(7) Uani 1 1 d . . . H21A H 0.2472 0.8344 0.4458 0.110 Uiso 1 1 calc R . . H21B H 0.3477 0.7573 0.4222 0.110 Uiso 1 1 calc R . . H21C H 0.2256 0.6977 0.4079 0.110 Uiso 1 1 calc R . . C22 C 0.7146(2) 1.2468(3) 0.38664(15) 0.0886(9) Uani 1 1 d . . . H22A H 0.7786 1.2875 0.3717 0.133 Uiso 1 1 calc R . . H22B H 0.7348 1.2195 0.4296 0.133 Uiso 1 1 calc R . . H22C H 0.6544 1.3122 0.3837 0.133 Uiso 1 1 calc R . . C23 C 0.7853(2) 0.7684(3) 0.31230(13) 0.0696(6) Uani 1 1 d . . . H23A H 0.8513 0.7878 0.2935 0.104 Uiso 1 1 calc R . . H23B H 0.7436 0.6959 0.2896 0.104 Uiso 1 1 calc R . . H23C H 0.8070 0.7409 0.3551 0.104 Uiso 1 1 calc R . . C24 C 0.4665(2) 0.6979(3) 0.00876(11) 0.0734(7) Uani 1 1 d . . . C25 C 0.1273(5) 0.7331(10) -0.0456(3) 0.155(2) Uani 1 1 d . . . H25 H 0.1315 0.6997 -0.0856 0.186 Uiso 1 1 calc R . . C26 C 0.1432(7) 0.8588(11) -0.0338(5) 0.186(3) Uani 1 1 d . . . H26 H 0.1632 0.9161 -0.0648 0.223 Uiso 1 1 calc R . . C27 C 0.1322(7) 0.9110(7) 0.0215(8) 0.208(4) Uani 1 1 d . . . H27 H 0.1439 1.0038 0.0294 0.250 Uiso 1 1 calc R . . C28 C 0.1046(6) 0.8299(16) 0.0645(4) 0.195(5) Uani 1 1 d . . . H28 H 0.0943 0.8655 0.1033 0.234 Uiso 1 1 calc R . . C29 C 0.0912(5) 0.6996(12) 0.0541(4) 0.177(3) Uani 1 1 d . . . H29 H 0.0723 0.6424 0.0854 0.212 Uiso 1 1 calc R . . C30 C 0.1044(4) 0.6488(5) -0.0008(5) 0.158(2) Uani 1 1 d . . . H30 H 0.0978 0.5552 -0.0082 0.190 Uiso 1 1 calc R . . H3 H 0.2027(18) 1.068(2) 0.2013(10) 0.057(6) Uiso 1 1 d . . . H5 H 0.4132(19) 0.873(2) 0.3419(10) 0.051(6) Uiso 1 1 d . . . H7 H 0.4085(14) 1.1114(18) 0.2180(8) 0.033(4) Uiso 1 1 d . . . H8 H 0.554(2) 0.946(3) 0.0458(12) 0.076(7) Uiso 1 1 d . . . H9 H 0.5245(18) 1.200(2) 0.3094(10) 0.050(5) Uiso 1 1 d . . . H13 H 0.5856(17) 0.820(2) 0.2475(10) 0.051(5) Uiso 1 1 d . . . H15 H 0.327(2) 0.773(2) 0.1878(12) 0.067(7) Uiso 1 1 d . . . H16 H 0.3471(19) 0.644(2) 0.0995(11) 0.060(6) Uiso 1 1 d . . . H19 H 0.5281(18) 1.066(2) 0.1351(10) 0.057(6) Uiso 1 1 d . . . H24 H 0.413(2) 0.601(3) 0.0026(12) 0.074(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 0.0416(7) 0.0869(11) 0.0560(9) 0.0123(8) 0.0207(7) 0.0009(7) O2 0.0460(8) 0.1035(14) 0.0695(11) -0.0200(9) 0.0012(7) 0.0002(9) O3 0.1159(16) 0.1267(17) 0.0576(11) -0.0124(10) 0.0440(11) 0.0141(13) C1 0.0379(9) 0.0520(10) 0.0415(9) -0.0005(7) 0.0124(7) -0.0001(7) C2 0.0396(9) 0.0524(10) 0.0424(10) -0.0009(7) 0.0078(7) 0.0037(8) C3 0.0433(10) 0.0529(10) 0.0372(9) 0.0016(7) 0.0105(7) 0.0042(8) C4 0.0416(9) 0.0461(9) 0.0361(8) -0.0013(7) 0.0121(7) 0.0016(7) C5 0.0379(9) 0.0579(11) 0.0392(9) 0.0044(7) 0.0081(7) 0.0038(8) C6 0.0425(9) 0.0579(11) 0.0397(9) 0.0047(7) 0.0117(7) 0.0002(8) C7 0.0436(9) 0.0476(10) 0.0388(9) 0.0016(7) 0.0138(7) -0.0003(7) C8 0.0405(9) 0.0524(10) 0.0401(9) 0.0007(7) 0.0151(7) -0.0038(8) C9 0.0481(10) 0.0540(11) 0.0480(11) -0.0043(8) 0.0171(8) -0.0020(9) C10 0.0518(11) 0.0658(13) 0.0491(11) -0.0118(9) 0.0145(9) -0.0087(9) C11 0.0412(10) 0.0727(13) 0.0456(10) -0.0051(9) 0.0121(8) -0.0052(9) C12 0.0413(9) 0.0642(12) 0.0497(11) -0.0022(9) 0.0163(8) 0.0016(8) C13 0.0453(10) 0.0538(11) 0.0468(10) -0.0054(8) 0.0132(8) -0.0040(8) C14 0.0403(9) 0.0527(10) 0.0372(9) 0.0051(7) 0.0115(7) 0.0025(8) C15 0.0589(12) 0.0571(11) 0.0456(10) 0.0003(8) 0.0229(9) -0.0036(9) C16 0.0674(14) 0.0583(12) 0.0507(12) -0.0055(9) 0.0183(10) -0.0026(10) C17 0.0551(11) 0.0696(13) 0.0390(10) -0.0008(8) 0.0125(8) 0.0113(10) C18 0.0543(12) 0.0806(15) 0.0402(10) 0.0079(9) 0.0188(9) 0.0029(11) C19 0.0537(11) 0.0646(13) 0.0428(10) 0.0040(8) 0.0171(9) -0.0085(10) C20 0.0451(11) 0.0779(15) 0.0644(14) 0.0105(11) 0.0071(10) 0.0082(10) C21 0.0545(13) 0.109(2) 0.0578(14) 0.0327(13) 0.0157(10) 0.0039(12) C22 0.0773(18) 0.0889(19) 0.095(2) -0.0366(16) -0.0045(15) -0.0036(14) C23 0.0497(12) 0.0783(15) 0.0811(17) -0.0118(12) 0.0098(11) 0.0106(11) C24 0.0853(17) 0.0881(18) 0.0504(13) -0.0059(11) 0.0221(12) 0.0188(15) C25 0.137(4) 0.226(7) 0.111(4) -0.057(4) 0.050(3) -0.010(5) C26 0.207(7) 0.177(7) 0.185(7) 0.085(6) 0.068(6) 0.028(6) C27 0.173(6) 0.106(4) 0.350(15) -0.063(7) 0.053(8) 0.010(4) C28 0.130(5) 0.322(13) 0.132(5) -0.103(7) 0.011(4) 0.036(8) C29 0.121(4) 0.280(9) 0.143(5) 0.094(6) 0.062(4) 0.032(6) C30 0.105(3) 0.115(3) 0.265(9) -0.030(5) 0.061(4) -0.018(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 C1 1.376(2) . ? O2 C11 1.368(3) . ? O3 C24 1.222(3) . ? C1 C6 1.387(3) . ? C1 C2 1.396(3) . ? C2 C3 1.389(3) . ? C2 C20 1.502(3) . ? C3 C4 1.393(2) . ? C4 C5 1.385(3) . ? C4 C7 1.523(2) . ? C5 C6 1.396(2) . ? C6 C21 1.507(3) . ? C7 C14 1.524(2) . ? C7 C8 1.525(3) . ? C8 C13 1.390(3) . ? C8 C9 1.391(3) . ? C9 C10 1.389(3) . ? C10 C11 1.397(3) . ? C10 C22 1.512(3) . ? C11 C12 1.392(3) . ? C12 C13 1.390(3) . ? C12 C23 1.506(3) . ? C14 C15 1.379(3) . ? C14 C19 1.401(3) . ? C15 C16 1.381(3) . ? C16 C17 1.388(3) . ? C17 C18 1.385(3) . ? C17 C24 1.462(3) . ? C18 C19 1.375(3) . ? C25 C26 1.264(9) . ? C25 C30 1.327(9) . ? C26 C27 1.319(12) . ? C27 C28 1.297(13) . ? C28 C29 1.299(11) . ? C29 C30 1.313(10) . ? 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 O1 C1 C6 122.03(16) . . ? O1 C1 C2 116.20(16) . . ? C6 C1 C2 121.76(16) . . ? C3 C2 C1 117.84(16) . . ? C3 C2 C20 121.14(17) . . ? C1 C2 C20 121.01(17) . . ? C2 C3 C4 122.39(17) . . ? C5 C4 C3 117.71(16) . . ? C5 C4 C7 123.12(16) . . ? C3 C4 C7 119.16(15) . . ? C4 C5 C6 122.11(17) . . ? C1 C6 C5 118.18(16) . . ? C1 C6 C21 120.99(17) . . ? C5 C6 C21 120.82(17) . . ? C4 C7 C14 113.32(15) . . ? C4 C7 C8 113.53(14) . . ? C14 C7 C8 110.42(14) . . ? C13 C8 C9 117.70(18) . . ? C13 C8 C7 122.06(16) . . ? C9 C8 C7 120.24(17) . . ? C10 C9 C8 122.17(19) . . ? C9 C10 C11 118.40(18) . . ? C9 C10 C22 120.9(2) . . ? C11 C10 C22 120.7(2) . . ? O2 C11 C12 122.31(19) . . ? O2 C11 C10 116.69(19) . . ? C12 C11 C10 120.99(18) . . ? C13 C12 C11 118.63(18) . . ? C13 C12 C23 120.00(19) . . ? C11 C12 C23 121.36(19) . . ? C8 C13 C12 122.06(18) . . ? C15 C14 C19 118.42(18) . . ? C15 C14 C7 123.23(16) . . ? C19 C14 C7 118.23(17) . . ? C14 C15 C16 120.76(19) . . ? C15 C16 C17 120.6(2) . . ? C18 C17 C16 119.06(19) . . ? C18 C17 C24 121.4(2) . . ? C16 C17 C24 119.5(2) . . ? C19 C18 C17 120.29(19) . . ? C18 C19 C14 120.9(2) . . ? O3 C24 C17 123.8(3) . . ? C26 C25 C30 119.8(6) . . ? C25 C26 C27 121.8(7) . . ? C28 C27 C26 118.5(7) . . ? C27 C28 C29 120.9(7) . . ? C28 C29 C30 119.9(7) . . ? C29 C30 C25 119.0(6) . . ? 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 O1 C1 C2 C3 178.49(17) . . . . ? C6 C1 C2 C3 -0.4(3) . . . . ? O1 C1 C2 C20 -0.3(3) . . . . ? C6 C1 C2 C20 -179.12(19) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C20 C2 C3 C4 178.84(18) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C2 C3 C4 C7 179.32(17) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C7 C4 C5 C6 -179.84(17) . . . . ? O1 C1 C6 C5 -178.96(18) . . . . ? C2 C1 C6 C5 -0.2(3) . . . . ? O1 C1 C6 C21 1.3(3) . . . . ? C2 C1 C6 C21 -179.9(2) . . . . ? C4 C5 C6 C1 1.0(3) . . . . ? C4 C5 C6 C21 -179.3(2) . . . . ? C5 C4 C7 C14 106.4(2) . . . . ? C3 C4 C7 C14 -72.1(2) . . . . ? C5 C4 C7 C8 -20.6(2) . . . . ? C3 C4 C7 C8 160.88(16) . . . . ? C4 C7 C8 C13 96.83(19) . . . . ? C14 C7 C8 C13 -31.7(2) . . . . ? C4 C7 C8 C9 -83.1(2) . . . . ? C14 C7 C8 C9 148.38(17) . . . . ? C13 C8 C9 C10 1.0(3) . . . . ? C7 C8 C9 C10 -179.06(17) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C8 C9 C10 C22 178.4(2) . . . . ? C9 C10 C11 O2 179.73(18) . . . . ? C22 C10 C11 O2 1.1(3) . . . . ? C9 C10 C11 C12 -1.7(3) . . . . ? C22 C10 C11 C12 179.7(2) . . . . ? O2 C11 C12 C13 -178.73(18) . . . . ? C10 C11 C12 C13 2.8(3) . . . . ? O2 C11 C12 C23 2.5(3) . . . . ? C10 C11 C12 C23 -176.0(2) . . . . ? C9 C8 C13 C12 0.1(3) . . . . ? C7 C8 C13 C12 -179.80(17) . . . . ? C11 C12 C13 C8 -2.0(3) . . . . ? C23 C12 C13 C8 176.79(19) . . . . ? C4 C7 C14 C15 -21.1(3) . . . . ? C8 C7 C14 C15 107.5(2) . . . . ? C4 C7 C14 C19 162.95(17) . . . . ? C8 C7 C14 C19 -68.4(2) . . . . ? C19 C14 C15 C16 1.0(3) . . . . ? C7 C14 C15 C16 -174.91(19) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C15 C16 C17 C18 -0.7(3) . . . . ? C15 C16 C17 C24 179.2(2) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C24 C17 C18 C19 -179.6(2) . . . . ? C17 C18 C19 C14 0.7(3) . . . . ? C15 C14 C19 C18 -1.4(3) . . . . ? C7 C14 C19 C18 174.72(18) . . . . ? C18 C17 C24 O3 2.8(4) . . . . ? C16 C17 C24 O3 -177.2(2) . . . . ? C30 C25 C26 C27 -3.5(12) . . . . ? C25 C26 C27 C28 0.2(13) . . . . ? C26 C27 C28 C29 1.9(13) . . . . ? C27 C28 C29 C30 -0.8(12) . . . . ? C28 C29 C30 C25 -2.5(10) . . . . ? C26 C25 C30 C29 4.6(10) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 30.56 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.411 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.067 # Attachment 'D4NO2.cif' data_d4no2_0m _database_code_depnum_ccdc_archive 'CCDC 281628' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;Bis(4-hydroxy-3,5-dimethylphenyl)(4-nitrophenyl)methane with benzene ; _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 N O4' _chemical_formula_sum 'C28 H28 N O4' _chemical_formula_weight 456.52 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.110(4) _cell_length_b 9.815(3) _cell_length_c 21.260(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.277(2) _cell_angle_gamma 90.00 _cell_volume 2506.73(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6430 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 29.66 _exptl_crystal_description plates _exptl_crystal_colour red _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.081 _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 0.71073 _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 30424 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 30.58 _reflns_number_total 7470 _reflns_number_gt 3693 _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^)+(0.0833P)^2^+0.3702P] 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 0.0001(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7470 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1362 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1966 _refine_ls_wR_factor_gt 0.1606 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.05401(11) 0.38625(17) 0.35725(8) 0.0714(4) Uani 1 1 d . . . O2 O 0.84190(14) 0.5650(2) 0.38307(10) 0.0945(6) Uani 1 1 d . . . O3 O 0.4153(2) 0.1128(3) -0.00222(11) 0.1323(8) Uani 1 1 d . . . O4 O 0.5382(2) 0.2547(2) -0.02582(9) 0.1186(8) Uani 1 1 d . . . N1 N 0.4707(2) 0.2147(3) 0.00841(10) 0.0857(6) Uani 1 1 d . . . C1 C 0.14643(14) 0.41671(18) 0.32832(8) 0.0508(4) Uani 1 1 d . . . C2 C 0.12781(14) 0.49271(17) 0.27265(8) 0.0495(4) Uani 1 1 d . . . C3 C 0.21930(14) 0.52727(17) 0.24316(8) 0.0484(4) Uani 1 1 d . . . H3 H 0.2082 0.5787 0.2062 0.058 Uiso 1 1 calc R . . C4 C 0.32717(13) 0.48841(16) 0.26650(8) 0.0443(4) Uani 1 1 d . . . C5 C 0.34111(14) 0.41203(18) 0.32142(8) 0.0503(4) Uani 1 1 d . . . H5 H 0.4125 0.3843 0.3376 0.060 Uiso 1 1 calc R . . C6 C 0.25239(14) 0.37501(18) 0.35341(8) 0.0515(4) Uani 1 1 d . . . C7 C 0.42292(14) 0.52928(17) 0.23058(8) 0.0466(4) Uani 1 1 d . . . H7 H 0.4073 0.6228 0.2160 0.056 Uiso 1 1 calc R . . C8 C 0.53551(13) 0.53382(17) 0.27156(8) 0.0469(4) Uani 1 1 d . . . C9 C 0.60773(14) 0.42418(19) 0.27749(9) 0.0537(4) Uani 1 1 d . . . H9 H 0.5867 0.3445 0.2555 0.064 Uiso 1 1 calc R . . C10 C 0.71045(15) 0.42819(19) 0.31498(10) 0.0580(5) Uani 1 1 d . . . C11 C 0.74059(16) 0.5489(2) 0.34656(10) 0.0637(5) Uani 1 1 d . . . C12 C 0.67079(17) 0.6605(2) 0.34246(10) 0.0652(5) Uani 1 1 d . . . C13 C 0.56871(16) 0.65079(19) 0.30485(9) 0.0575(5) Uani 1 1 d . . . H13 H 0.5211 0.7255 0.3020 0.069 Uiso 1 1 calc R . . C14 C 0.42998(14) 0.44465(17) 0.17115(8) 0.0476(4) Uani 1 1 d . . . C15 C 0.49811(16) 0.4897(2) 0.12781(9) 0.0621(5) Uani 1 1 d . . . H15 H 0.5349 0.5725 0.1347 0.075 Uiso 1 1 calc R . . C16 C 0.51259(17) 0.4151(2) 0.07493(9) 0.0685(6) Uani 1 1 d . . . H16 H 0.5593 0.4458 0.0464 0.082 Uiso 1 1 calc R . . C17 C 0.45672(17) 0.2945(2) 0.06513(9) 0.0622(5) Uani 1 1 d . . . C18 C 0.38764(19) 0.2468(2) 0.10592(10) 0.0695(6) Uani 1 1 d . . . H18 H 0.3499 0.1648 0.0980 0.083 Uiso 1 1 calc R . . C19 C 0.37471(17) 0.32262(19) 0.15947(9) 0.0601(5) Uani 1 1 d . . . H19 H 0.3282 0.2909 0.1879 0.072 Uiso 1 1 calc R . . C20 C 0.01228(15) 0.5384(2) 0.24675(11) 0.0700(6) Uani 1 1 d . . . H20A H 0.0156 0.5930 0.2096 0.105 Uiso 1 1 calc R . . H20B H -0.0188 0.5912 0.2782 0.105 Uiso 1 1 calc R . . H20C H -0.0337 0.4601 0.2359 0.105 Uiso 1 1 calc R . . C21 C 0.27079(19) 0.2926(3) 0.41396(11) 0.0826(7) Uani 1 1 d . . . H21A H 0.2486 0.3453 0.4483 0.124 Uiso 1 1 calc R . . H21B H 0.3482 0.2695 0.4231 0.124 Uiso 1 1 calc R . . H21C H 0.2272 0.2107 0.4089 0.124 Uiso 1 1 calc R . . C22 C 0.78486(18) 0.3045(2) 0.32084(13) 0.0802(7) Uani 1 1 d . . . H22A H 0.8505 0.3228 0.3012 0.120 Uiso 1 1 calc R . . H22B H 0.7458 0.2285 0.3001 0.120 Uiso 1 1 calc R . . H22C H 0.8057 0.2836 0.3648 0.120 Uiso 1 1 calc R . . C23 C 0.7051(2) 0.7910(3) 0.37754(16) 0.1082(10) Uani 1 1 d . . . H23A H 0.7583 0.8385 0.3558 0.162 Uiso 1 1 calc R . . H23B H 0.7380 0.7697 0.4199 0.162 Uiso 1 1 calc R . . H23C H 0.6409 0.8475 0.3792 0.162 Uiso 1 1 calc R . . C24 C 0.8892(6) 0.6402(12) 0.9367(3) 0.206(4) Uani 1 1 d . . . H24 H 0.8936 0.5900 0.9000 0.247 Uiso 1 1 calc R . . C25 C 0.9050(5) 0.7773(13) 0.9371(4) 0.210(4) Uani 1 1 d . . . H25 H 0.9193 0.8227 0.9006 0.252 Uiso 1 1 calc R . . C26 C 0.8995(4) 0.8465(5) 0.9919(6) 0.185(3) Uani 1 1 d . . . H26 H 0.9089 0.9405 0.9936 0.222 Uiso 1 1 calc R . . C27 C 0.8800(4) 0.7761(10) 1.0434(3) 0.171(2) Uani 1 1 d . . . H27 H 0.8799 0.8190 1.0824 0.206 Uiso 1 1 calc R . . C28 C 0.8614(6) 0.6462(8) 1.0371(4) 0.191(2) Uani 1 1 d . . . H28 H 0.8418 0.5989 1.0720 0.229 Uiso 1 1 calc R . . C29 C 0.8679(6) 0.5810(6) 0.9878(5) 0.202(3) Uani 1 1 d . . . H29 H 0.8572 0.4871 0.9877 0.243 Uiso 1 1 calc R . . H1O H 0.071(2) 0.350(3) 0.3928(14) 0.094(9) Uiso 1 1 d . . . H2O H 0.869(2) 0.487(3) 0.3865(14) 0.109(11) 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 0.0487(8) 0.0970(11) 0.0709(10) 0.0146(9) 0.0169(7) -0.0039(7) O2 0.0638(10) 0.0920(13) 0.1183(15) -0.0115(11) -0.0253(9) -0.0093(9) O3 0.1347(18) 0.150(2) 0.1135(16) -0.0706(15) 0.0218(13) -0.0055(16) O4 0.167(2) 0.1252(16) 0.0740(12) -0.0028(11) 0.0557(14) 0.0294(15) N1 0.0941(16) 0.1007(16) 0.0619(12) -0.0122(11) 0.0082(12) 0.0321(13) C1 0.0439(9) 0.0539(10) 0.0559(10) -0.0013(8) 0.0115(8) -0.0039(7) C2 0.0449(9) 0.0508(9) 0.0520(10) -0.0027(8) 0.0025(8) 0.0040(7) C3 0.0493(10) 0.0494(9) 0.0463(9) 0.0030(7) 0.0051(8) 0.0046(7) C4 0.0437(9) 0.0448(8) 0.0448(9) -0.0007(7) 0.0070(7) 0.0013(7) C5 0.0426(9) 0.0568(10) 0.0512(10) 0.0062(8) 0.0041(8) 0.0043(8) C6 0.0472(10) 0.0585(10) 0.0488(10) 0.0065(8) 0.0063(8) -0.0006(8) C7 0.0476(9) 0.0452(9) 0.0476(9) 0.0043(7) 0.0081(8) 0.0010(7) C8 0.0424(9) 0.0507(9) 0.0489(9) 0.0022(7) 0.0111(7) -0.0058(7) C9 0.0471(10) 0.0538(10) 0.0608(11) -0.0022(8) 0.0087(8) -0.0069(8) C10 0.0453(10) 0.0629(11) 0.0664(12) 0.0035(9) 0.0093(9) -0.0021(8) C11 0.0484(10) 0.0723(13) 0.0686(12) 0.0004(10) 0.0006(9) -0.0095(9) C12 0.0590(11) 0.0653(12) 0.0696(13) -0.0081(10) 0.0023(10) -0.0127(10) C13 0.0559(11) 0.0526(10) 0.0647(11) -0.0023(8) 0.0101(9) -0.0041(8) C14 0.0432(9) 0.0538(10) 0.0459(9) 0.0064(7) 0.0061(7) 0.0037(7) C15 0.0616(12) 0.0732(13) 0.0531(11) 0.0051(9) 0.0127(9) -0.0069(10) C16 0.0638(12) 0.0930(16) 0.0506(11) 0.0081(11) 0.0153(9) 0.0067(11) C17 0.0643(12) 0.0773(13) 0.0442(10) -0.0016(9) 0.0045(9) 0.0224(11) C18 0.0799(14) 0.0605(12) 0.0684(13) -0.0110(10) 0.0111(12) 0.0019(10) C19 0.0673(12) 0.0577(11) 0.0579(11) -0.0022(9) 0.0176(9) -0.0024(9) C20 0.0474(11) 0.0794(14) 0.0816(14) 0.0069(11) 0.0024(10) 0.0096(9) C21 0.0651(13) 0.1101(18) 0.0725(14) 0.0369(13) 0.0087(11) -0.0024(12) C22 0.0549(12) 0.0831(15) 0.1008(18) 0.0001(13) 0.0030(12) 0.0107(11) C23 0.0999(19) 0.0838(17) 0.131(2) -0.0364(16) -0.0246(17) -0.0078(15) C24 0.181(5) 0.331(11) 0.100(3) -0.043(5) -0.008(4) 0.105(7) C25 0.163(5) 0.295(9) 0.191(7) 0.136(7) 0.093(5) 0.078(6) C26 0.121(3) 0.126(3) 0.321(9) -0.009(5) 0.077(5) -0.013(3) C27 0.145(4) 0.243(7) 0.133(4) -0.062(4) 0.046(3) -0.019(5) C28 0.270(7) 0.148(4) 0.157(5) 0.056(4) 0.037(5) 0.010(5) C29 0.255(7) 0.134(4) 0.209(7) -0.053(5) -0.001(6) 0.036(4) _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 C1 O1 1.377(2) . ? C1 C6 1.387(2) . ? C1 C2 1.393(2) . ? C2 C3 1.383(2) . ? C2 C20 1.506(2) . ? C3 C4 1.391(2) . ? C4 C5 1.380(2) . ? C4 C7 1.521(2) . ? C5 C6 1.391(2) . ? C6 C21 1.513(3) . ? C7 C8 1.523(2) . ? C7 C14 1.523(2) . ? C8 C13 1.381(2) . ? C8 C9 1.382(2) . ? C9 C10 1.390(2) . ? C10 C11 1.388(3) . ? C10 C22 1.507(3) . ? C11 O2 1.375(2) . ? C11 C12 1.380(3) . ? C12 C13 1.388(3) . ? C12 C23 1.513(3) . ? C14 C19 1.379(3) . ? C14 C15 1.385(3) . ? C15 C16 1.371(3) . ? C16 C17 1.366(3) . ? C17 C18 1.362(3) . ? C17 N1 1.466(3) . ? C18 C19 1.386(3) . ? C24 C29 1.287(9) . ? C24 C25 1.359(10) . ? C25 C26 1.356(10) . ? C26 C27 1.341(9) . ? C27 C28 1.299(7) . ? C28 C29 1.240(8) . ? N1 O3 1.210(3) . ? N1 O4 1.226(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 O1 C1 C6 121.93(17) . . ? O1 C1 C2 116.27(16) . . ? C6 C1 C2 121.80(16) . . ? C3 C2 C1 117.64(15) . . ? C3 C2 C20 121.47(16) . . ? C1 C2 C20 120.88(17) . . ? C2 C3 C4 122.78(15) . . ? C5 C4 C3 117.36(15) . . ? C5 C4 C7 123.30(15) . . ? C3 C4 C7 119.34(14) . . ? C4 C5 C6 122.45(15) . . ? C5 C6 C1 117.97(16) . . ? C5 C6 C21 121.08(16) . . ? C1 C6 C21 120.94(17) . . ? C4 C7 C8 113.87(13) . . ? C4 C7 C14 113.52(14) . . ? C8 C7 C14 110.50(13) . . ? C13 C8 C9 117.43(16) . . ? C13 C8 C7 119.92(15) . . ? C9 C8 C7 122.65(15) . . ? C8 C9 C10 122.68(17) . . ? C9 C10 C11 117.58(17) . . ? C9 C10 C22 120.44(18) . . ? C11 C10 C22 121.98(18) . . ? O2 C11 C12 116.08(19) . . ? O2 C11 C10 122.18(19) . . ? C12 C11 C10 121.74(17) . . ? C11 C12 C13 118.39(18) . . ? C11 C12 C23 120.86(19) . . ? C13 C12 C23 120.7(2) . . ? C8 C13 C12 122.17(18) . . ? C19 C14 C15 118.29(17) . . ? C19 C14 C7 123.09(16) . . ? C15 C14 C7 118.59(16) . . ? C16 C15 C14 121.58(19) . . ? C17 C16 C15 118.4(2) . . ? C18 C17 C16 122.22(19) . . ? C18 C17 N1 119.0(2) . . ? C16 C17 N1 118.8(2) . . ? C17 C18 C19 118.7(2) . . ? C14 C19 C18 120.78(19) . . ? C29 C24 C25 119.0(6) . . ? C26 C25 C24 118.7(6) . . ? C27 C26 C25 118.4(6) . . ? C28 C27 C26 117.9(5) . . ? C29 C28 C27 124.4(6) . . ? C28 C29 C24 121.5(7) . . ? O3 N1 O4 123.4(2) . . ? O3 N1 C17 118.4(3) . . ? O4 N1 C17 118.2(3) . . ? 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 O1 C1 C2 C3 178.73(16) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? O1 C1 C2 C20 0.3(3) . . . . ? C6 C1 C2 C20 -179.22(18) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C20 C2 C3 C4 178.97(17) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C2 C3 C4 C7 179.21(15) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C7 C4 C5 C6 -179.63(16) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C4 C5 C6 C21 -179.25(19) . . . . ? O1 C1 C6 C5 -179.13(17) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? O1 C1 C6 C21 0.5(3) . . . . ? C2 C1 C6 C21 179.95(19) . . . . ? C5 C4 C7 C8 -24.6(2) . . . . ? C3 C4 C7 C8 156.36(15) . . . . ? C5 C4 C7 C14 103.03(18) . . . . ? C3 C4 C7 C14 -76.03(19) . . . . ? C4 C7 C8 C13 -86.47(19) . . . . ? C14 C7 C8 C13 144.38(16) . . . . ? C4 C7 C8 C9 93.30(19) . . . . ? C14 C7 C8 C9 -35.8(2) . . . . ? C13 C8 C9 C10 -0.1(3) . . . . ? C7 C8 C9 C10 -179.89(16) . . . . ? C8 C9 C10 C11 -1.0(3) . . . . ? C8 C9 C10 C22 178.67(19) . . . . ? C9 C10 C11 O2 -177.72(19) . . . . ? C22 C10 C11 O2 2.7(3) . . . . ? C9 C10 C11 C12 1.5(3) . . . . ? C22 C10 C11 C12 -178.1(2) . . . . ? O2 C11 C12 C13 178.32(19) . . . . ? C10 C11 C12 C13 -0.9(3) . . . . ? O2 C11 C12 C23 -1.0(3) . . . . ? C10 C11 C12 C23 179.7(2) . . . . ? C9 C8 C13 C12 0.7(3) . . . . ? C7 C8 C13 C12 -179.50(17) . . . . ? C11 C12 C13 C8 -0.2(3) . . . . ? C23 C12 C13 C8 179.1(2) . . . . ? C4 C7 C14 C19 -15.6(2) . . . . ? C8 C7 C14 C19 113.75(18) . . . . ? C4 C7 C14 C15 166.77(15) . . . . ? C8 C7 C14 C15 -63.90(19) . . . . ? C19 C14 C15 C16 -1.0(3) . . . . ? C7 C14 C15 C16 176.72(17) . . . . ? C14 C15 C16 C17 0.8(3) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? C15 C16 C17 N1 179.37(17) . . . . ? C16 C17 C18 C19 -0.7(3) . . . . ? N1 C17 C18 C19 180.00(18) . . . . ? C15 C14 C19 C18 0.4(3) . . . . ? C7 C14 C19 C18 -177.27(17) . . . . ? C17 C18 C19 C14 0.5(3) . . . . ? C29 C24 C25 C26 1.0(10) . . . . ? C24 C25 C26 C27 0.9(9) . . . . ? C25 C26 C27 C28 -3.8(9) . . . . ? C26 C27 C28 C29 5.2(11) . . . . ? C27 C28 C29 C24 -3.4(12) . . . . ? C25 C24 C29 C28 0.2(11) . . . . ? C18 C17 N1 O3 4.3(3) . . . . ? C16 C17 N1 O3 -175.0(2) . . . . ? C18 C17 N1 O4 -175.7(2) . . . . ? C16 C17 N1 O4 5.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 30.58 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.160 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.033 # Attachment 'Phenol_01.cif' data_jbb05029 _database_code_depnum_ccdc_archive 'CCDC 281629' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(4-hydroxyphenyl)phenylmethane ; _chemical_name_common Bis(4-hydroxyphenyl)phenylmethane _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 O2. 1/6 H2 O' _chemical_formula_sum 'C114 H98 O13' _chemical_formula_weight 1675.92 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 Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 35.873(2) _cell_length_b 35.873(2) _cell_length_c 6.108(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6808.04(12) _cell_formula_units_Z 18 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7104 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.49 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2610 _exptl_absorpt_coefficient_mu 0.077 _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 0.71073 _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 39812 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0113 _diffrn_reflns_limit_h_min -47 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3762 _reflns_number_gt 2797 _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^)+(0.0893P)^2^+6.1328P] 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 0.0000(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3762 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1841 _refine_ls_wR_factor_gt 0.1643 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.003 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 0.69073(5) 0.03018(4) 0.7903(3) 0.0635(4) Uani 1 1 d . . . O2 O 0.68600(8) 0.28962(7) 0.5048(4) 0.0968(6) Uani 1 1 d . . . O3 O 0.6667 0.3333 0.8333 0.0923(13) Uani 1 6 d S . . H1O H 0.6741(8) 0.0213(8) 0.892(4) 0.071(7) Uiso 1 1 d . . . H2O H 0.6644(5) 0.2745(5) 0.576(2) 0.016(4) Uiso 1 1 d . . . C1 C 0.71290(5) 0.07431(5) 0.7836(3) 0.0492(4) Uani 1 1 d . . . C2 C 0.73920(7) 0.09404(6) 0.6062(3) 0.0612(5) Uani 1 1 d . . . H2 H 0.7413 0.0776 0.4944 0.073 Uiso 1 1 calc R . . C3 C 0.76237(6) 0.13844(6) 0.5958(3) 0.0581(5) Uani 1 1 d . . . H3 H 0.7801 0.1515 0.4756 0.070 Uiso 1 1 calc R . . C4 C 0.76014(5) 0.16407(5) 0.7584(3) 0.0470(4) Uani 1 1 d . . . C5 C 0.73381(6) 0.14325(6) 0.9374(3) 0.0543(4) Uani 1 1 d . . . H5 H 0.6934(7) 0.0857(7) 1.073(4) 0.065(6) Uiso 1 1 d . . . C6 C 0.71043(6) 0.09890(6) 0.9503(3) 0.0541(4) Uani 1 1 d . . . C7 C 0.78537(6) 0.21279(5) 0.7350(3) 0.0495(4) Uani 1 1 d . . . H7 H 0.8047(6) 0.2189(6) 0.611(3) 0.053(5) Uiso 1 1 d . . . C8 C 0.75646(6) 0.23091(5) 0.6743(3) 0.0517(4) Uani 1 1 d . . . H8 H 0.7319 0.1596 1.0506 0.065 Uiso 1 1 calc R . . C9 C 0.75995(11) 0.24898(10) 0.4721(4) 0.0895(8) Uani 1 1 d . . . H9 H 0.7791 0.2486 0.3704 0.107 Uiso 1 1 calc R . . C10 C 0.73580(13) 0.26769(11) 0.4162(4) 0.1069(11) Uani 1 1 d . . . H10 H 0.7389 0.2798 0.2782 0.128 Uiso 1 1 calc R . . C11 C 0.70766(8) 0.26847(7) 0.5610(4) 0.0730(6) Uani 1 1 d . . . C12 C 0.70266(8) 0.24996(8) 0.7644(5) 0.0791(7) Uani 1 1 d . . . H12 H 0.6829 0.2498 0.8637 0.095 Uiso 1 1 calc R . . C13 C 0.72739(8) 0.23162(8) 0.8189(4) 0.0723(6) Uani 1 1 d . . . H13 H 0.7243(10) 0.2193(9) 0.961(5) 0.103(9) Uiso 1 1 d . . . C14 C 0.81532(5) 0.23685(6) 0.9256(3) 0.0513(4) Uani 1 1 d . . . C15 C 0.83004(6) 0.21700(6) 1.0688(3) 0.0577(5) Uani 1 1 d . . . H15 H 0.8196 0.1876 1.0560 0.069 Uiso 1 1 calc R . . C16 C 0.85977(7) 0.23981(8) 1.2293(4) 0.0705(6) Uani 1 1 d . . . H16 H 0.8690 0.2257 1.3238 0.085 Uiso 1 1 calc R . . C17 C 0.87563(8) 0.28281(8) 1.2497(5) 0.0870(7) Uani 1 1 d . . . H17 H 0.8958 0.2983 1.3576 0.104 Uiso 1 1 calc R . . C18 C 0.86181(9) 0.30340(8) 1.1109(5) 0.0981(9) Uani 1 1 d . . . H18 H 0.8729 0.3329 1.1243 0.118 Uiso 1 1 calc R . . C19 C 0.83166(8) 0.28077(7) 0.9518(4) 0.0784(7) Uani 1 1 d . . . H19 H 0.8221 0.2951 0.8608 0.094 Uiso 1 1 calc R . . 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 0.0648(8) 0.0470(7) 0.0689(9) -0.0042(6) 0.0142(7) 0.0205(6) O2 0.1266(18) 0.1034(15) 0.0975(14) -0.0108(12) -0.0195(13) 0.0853(15) O3 0.107(2) 0.107(2) 0.062(2) 0.000 0.000 0.0536(10) C1 0.0444(8) 0.0464(8) 0.0552(9) -0.0017(7) 0.0022(7) 0.0214(7) C2 0.0704(12) 0.0567(10) 0.0541(10) -0.0059(8) 0.0131(9) 0.0300(9) C3 0.0642(11) 0.0571(10) 0.0495(9) 0.0032(7) 0.0177(8) 0.0277(9) C4 0.0451(8) 0.0499(9) 0.0482(8) 0.0026(7) 0.0062(6) 0.0254(7) C5 0.0590(10) 0.0511(9) 0.0527(9) -0.0012(7) 0.0146(7) 0.0273(8) C6 0.0524(9) 0.0517(9) 0.0564(10) 0.0043(8) 0.0164(8) 0.0246(8) C7 0.0504(9) 0.0489(9) 0.0483(9) 0.0065(7) 0.0123(7) 0.0241(7) C8 0.0574(10) 0.0467(8) 0.0495(9) 0.0011(7) 0.0021(7) 0.0250(8) C9 0.144(2) 0.120(2) 0.0503(11) 0.0154(12) 0.0206(13) 0.100(2) C10 0.200(4) 0.142(3) 0.0475(11) 0.0033(13) -0.0014(15) 0.137(3) C11 0.0965(16) 0.0649(12) 0.0763(13) -0.0193(10) -0.0297(12) 0.0544(12) C12 0.0756(14) 0.0775(14) 0.0986(17) 0.0218(12) 0.0215(12) 0.0491(12) C13 0.0775(14) 0.0808(14) 0.0743(13) 0.0304(11) 0.0245(11) 0.0514(12) C14 0.0419(8) 0.0481(9) 0.0582(10) 0.0056(7) 0.0091(7) 0.0184(7) C15 0.0506(9) 0.0564(10) 0.0693(11) -0.0011(8) 0.0014(8) 0.0290(8) C16 0.0547(11) 0.0745(13) 0.0836(14) -0.0045(11) -0.0092(10) 0.0333(10) C17 0.0669(14) 0.0729(15) 0.1025(19) -0.0149(13) -0.0258(13) 0.0210(12) C18 0.0952(18) 0.0510(12) 0.122(2) -0.0090(13) -0.0271(17) 0.0167(12) C19 0.0800(15) 0.0480(10) 0.0909(16) 0.0073(10) -0.0148(12) 0.0198(10) _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 C1 O1 1.372(2) . ? C1 C2 1.378(3) . ? C3 C2 1.381(3) . ? C4 C3 1.382(2) . ? C4 C5 1.393(2) . ? C6 C1 1.379(2) . ? C6 C5 1.381(3) . ? C7 C8 1.519(2) . ? C7 C4 1.521(2) . ? C7 C14 1.526(3) . ? C8 C9 1.371(3) . ? C8 C13 1.376(3) . ? C9 C10 1.378(3) . ? C11 C10 1.353(4) . ? C11 O2 1.374(3) . ? C11 C12 1.377(3) . ? C13 C12 1.384(3) . ? C14 C15 1.388(3) . ? C14 C19 1.388(3) . ? C15 C16 1.377(3) . ? C16 C17 1.357(3) . ? C17 C18 1.370(4) . ? C19 C18 1.376(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C7 C4 111.92(14) . . ? C8 C7 C14 112.49(14) . . ? C4 C7 C14 115.13(14) . . ? C3 C4 C5 117.16(16) . . ? C3 C4 C7 119.87(15) . . ? C5 C4 C7 122.97(15) . . ? C15 C14 C19 117.14(18) . . ? C15 C14 C7 122.12(16) . . ? C19 C14 C7 120.55(17) . . ? C1 C6 C5 119.91(16) . . ? O1 C1 C2 117.98(16) . . ? O1 C1 C6 122.07(16) . . ? C2 C1 C6 119.92(16) . . ? C6 C5 C4 121.40(16) . . ? C9 C8 C13 117.39(19) . . ? C9 C8 C7 120.10(18) . . ? C13 C8 C7 122.46(16) . . ? C16 C15 C14 121.60(19) . . ? C2 C3 C4 122.18(16) . . ? C1 C2 C3 119.42(16) . . ? C17 C16 C15 120.1(2) . . ? C10 C11 O2 118.8(2) . . ? C10 C11 C12 119.9(2) . . ? O2 C11 C12 121.2(2) . . ? C8 C13 C12 121.8(2) . . ? C16 C17 C18 119.8(2) . . ? C18 C19 C14 120.8(2) . . ? C11 C12 C13 119.1(2) . . ? C8 C9 C10 121.5(2) . . ? C11 C10 C9 120.4(2) . . ? C17 C18 C19 120.5(2) . . ? 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 C8 C7 C4 C3 104.56(19) . . . . ? C14 C7 C4 C3 -125.35(18) . . . . ? C8 C7 C4 C5 -74.6(2) . . . . ? C14 C7 C4 C5 55.5(2) . . . . ? C8 C7 C14 C15 151.21(16) . . . . ? C4 C7 C14 C15 21.4(2) . . . . ? C8 C7 C14 C19 -33.9(2) . . . . ? C4 C7 C14 C19 -163.75(18) . . . . ? C5 C6 C1 O1 179.15(18) . . . . ? C5 C6 C1 C2 1.0(3) . . . . ? C1 C6 C5 C4 0.0(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C7 C4 C5 C6 178.19(17) . . . . ? C4 C7 C8 C9 -112.1(2) . . . . ? C14 C7 C8 C9 116.5(2) . . . . ? C4 C7 C8 C13 70.6(2) . . . . ? C14 C7 C8 C13 -60.9(2) . . . . ? C19 C14 C15 C16 -0.4(3) . . . . ? C7 C14 C15 C16 174.64(17) . . . . ? C5 C4 C3 C2 1.0(3) . . . . ? C7 C4 C3 C2 -178.22(18) . . . . ? O1 C1 C2 C3 -179.23(18) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? C4 C3 C2 C1 0.0(3) . . . . ? C14 C15 C16 C17 -0.4(3) . . . . ? C9 C8 C13 C12 -0.3(4) . . . . ? C7 C8 C13 C12 177.1(2) . . . . ? C15 C16 C17 C18 0.3(4) . . . . ? C15 C14 C19 C18 1.2(4) . . . . ? C7 C14 C19 C18 -173.9(2) . . . . ? C10 C11 C12 C13 1.4(4) . . . . ? O2 C11 C12 C13 -175.5(2) . . . . ? C8 C13 C12 C11 -0.8(4) . . . . ? C13 C8 C9 C10 0.9(4) . . . . ? C7 C8 C9 C10 -176.6(3) . . . . ? O2 C11 C10 C9 176.2(3) . . . . ? C12 C11 C10 C9 -0.9(5) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C16 C17 C18 C19 0.5(5) . . . . ? C14 C19 C18 C17 -1.3(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.333 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.039 # Attachment 'D4NH2.cif' data_bisphenol_0m _database_code_depnum_ccdc_archive 'CCDC 281630' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ;Bis(4-hydroxy-2,6-dimethylphenyl)(4- aminophenyl)methane:Toluene solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H33 N O2' _chemical_formula_sum 'C30 H33 N O2' _chemical_formula_weight 439.57 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' _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 11.482(12) _cell_length_b 11.739(11) _cell_length_c 12.465(13) _cell_angle_alpha 62.491(6) _cell_angle_beta 63.027(6) _cell_angle_gamma 62.880(6) _cell_volume 1262.2(2) _cell_formula_units_Z 3 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4744 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 30.21 _exptl_crystal_description flakes _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.07 _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 0.71073 _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 17639 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.1094 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 30.72 _reflns_number_total 6884 _reflns_number_gt 3048 _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^)+(0.0798P)^2^+8.4807P] 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 0.001(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6884 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2620 _refine_ls_wR_factor_gt 0.2325 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _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 0.9318(5) 0.1442(6) 0.2577(6) 0.0567(15) Uani 1 1 d . . . O2 O 0.1638(6) 0.9323(5) 0.2185(6) 0.0618(17) Uani 1 1 d . . . H1O H 0.987(8) 0.182(8) 0.190(8) 0.05(2) Uiso 1 1 d . . . H2O H 0.087(8) 0.950(8) 0.258(7) 0.04(2) Uiso 1 1 d . . . N1 N 0.1556(7) 0.2273(9) 0.0589(7) 0.0534(17) Uani 1 1 d . . . H1N H 0.164(8) 0.283(9) -0.026(9) 0.06(2) Uiso 1 1 d . . . H2N H 0.196(10) 0.142(12) 0.054(10) 0.09(4) Uiso 1 1 d . . . C1 C 0.7941(6) 0.1970(7) 0.2668(7) 0.0415(16) Uani 1 1 d . . . C2 C 0.7529(6) 0.2314(7) 0.1636(7) 0.0408(15) Uani 1 1 d . . . C3 C 0.6117(6) 0.2836(7) 0.1797(7) 0.0394(15) Uani 1 1 d . . . H3 H 0.583(7) 0.321(7) 0.111(7) 0.036(18) Uiso 1 1 d . . . C4 C 0.5161(6) 0.3031(6) 0.2919(6) 0.0368(14) Uani 1 1 d . . . C5 C 0.5614(7) 0.2637(8) 0.3938(7) 0.0460(17) Uani 1 1 d . . . H5 H 0.487(9) 0.280(9) 0.476(9) 0.07(3) Uiso 1 1 d . . . C6 C 0.7015(7) 0.2096(8) 0.3828(7) 0.0474(17) Uani 1 1 d . . . C7 C 0.3616(6) 0.3655(6) 0.3127(7) 0.0357(14) Uani 1 1 d . . . H7 H 0.313(7) 0.316(7) 0.412(7) 0.045(19) Uiso 1 1 d . . . C8 C 0.3126(6) 0.5183(6) 0.2897(7) 0.0369(15) Uani 1 1 d . . . C9 C 0.1860(6) 0.5750(7) 0.3675(7) 0.0411(16) Uani 1 1 d . . . H9 H 0.1360 0.5187 0.4345 0.049 Uiso 1 1 calc R . . C10 C 0.1318(6) 0.7127(8) 0.3482(7) 0.0459(17) Uani 1 1 d . . . C11 C 0.2079(6) 0.7947(7) 0.2474(7) 0.0426(16) Uani 1 1 d . . . C12 C 0.3370(6) 0.7405(7) 0.1693(7) 0.0413(16) Uani 1 1 d . . . C13 C 0.3860(6) 0.6032(8) 0.1930(7) 0.0427(16) Uani 1 1 d . . . H13 H 0.468(7) 0.580(7) 0.142(7) 0.040(19) Uiso 1 1 d . . . C14 C 0.3119(6) 0.3318(6) 0.2388(7) 0.0356(14) Uani 1 1 d . . . C15 C 0.2982(7) 0.2061(8) 0.2838(8) 0.0482(18) Uani 1 1 d . . . H15 H 0.3216 0.1432 0.3568 0.058 Uiso 1 1 calc R . . C16 C 0.2498(8) 0.1700(8) 0.2226(8) 0.0489(18) Uani 1 1 d . . . H16 H 0.237(8) 0.083(9) 0.260(8) 0.06(2) Uiso 1 1 d . . . C17 C 0.2122(6) 0.2627(7) 0.1159(7) 0.0417(16) Uani 1 1 d . . . C18 C 0.2269(8) 0.3876(8) 0.0692(8) 0.0509(18) Uani 1 1 d . . . H18 H 0.2048 0.4499 -0.0045 0.061 Uiso 1 1 calc R . . C19 C 0.2755(8) 0.4230(8) 0.1317(8) 0.0469(18) Uani 1 1 d . . . H19 H 0.284(8) 0.499(8) 0.107(7) 0.05(2) Uiso 1 1 d . . . C20 C 0.8563(8) 0.2080(9) 0.0424(8) 0.061(2) Uani 1 1 d . . . H20A H 0.9137 0.2643 0.0049 0.092 Uiso 1 1 calc R . . H20B H 0.8098 0.2299 -0.0153 0.092 Uiso 1 1 calc R . . H20C H 0.9121 0.1149 0.0595 0.092 Uiso 1 1 calc R . . C21 C 0.7489(9) 0.1685(12) 0.4938(9) 0.078(3) Uani 1 1 d . . . H21A H 0.8155 0.0800 0.5038 0.117 Uiso 1 1 calc R . . H21B H 0.6716 0.1672 0.5698 0.117 Uiso 1 1 calc R . . H21C H 0.7899 0.2320 0.4786 0.117 Uiso 1 1 calc R . . C22 C -0.0050(8) 0.7700(9) 0.4365(9) 0.063(2) Uani 1 1 d . . . H22A H 0.0084 0.8092 0.4810 0.094 Uiso 1 1 calc R . . H22B H -0.0445 0.6989 0.4967 0.094 Uiso 1 1 calc R . . H22C H -0.0659 0.8381 0.3880 0.094 Uiso 1 1 calc R . . C23 C 0.4159(8) 0.8333(8) 0.0623(9) 0.063(2) Uani 1 1 d . . . H23A H 0.5013 0.7815 0.0170 0.094 Uiso 1 1 calc R . . H23B H 0.4341 0.8804 0.0958 0.094 Uiso 1 1 calc R . . H23C H 0.3628 0.8975 0.0054 0.094 Uiso 1 1 calc R . . C24 C 0.334(3) 0.0945(18) 0.7377(19) 0.242(14) Uani 1 1 d . . . H24A H 0.3790 0.0903 0.6526 0.363 Uiso 1 1 calc R . . H24B H 0.2587 0.0581 0.7775 0.363 Uiso 1 1 calc R . . H24C H 0.3978 0.0426 0.7854 0.363 Uiso 1 1 calc R . . C25 C 0.284(3) 0.2276(15) 0.7342(12) 0.133(7) Uani 1 1 d . . . C26 C 0.1462(16) 0.304(2) 0.7402(11) 0.099(4) Uani 1 1 d . . . H26 H 0.0884 0.2643 0.7459 0.119 Uiso 1 1 calc R . . C27 C 0.0988(19) 0.427(2) 0.7379(14) 0.136(7) Uani 1 1 d . . . H27 H 0.0059 0.4717 0.7461 0.163 Uiso 1 1 calc R . . C28 C 0.173(3) 0.495(2) 0.7249(17) 0.139(6) Uani 1 1 d . . . H28 H 0.1325 0.5852 0.7211 0.167 Uiso 1 1 calc R . . C29 C 0.301(3) 0.434(3) 0.7174(15) 0.151(8) Uani 1 1 d . . . H29 H 0.3540 0.4817 0.7067 0.182 Uiso 1 1 calc R . . C30 C 0.3622(14) 0.294(2) 0.7255(12) 0.110(5) Uani 1 1 d . . . H30 H 0.4532 0.2487 0.7249 0.132 Uiso 1 1 calc R . . 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 0.034(3) 0.059(4) 0.061(4) -0.014(3) -0.018(3) -0.004(2) O2 0.046(3) 0.040(3) 0.088(5) -0.033(3) -0.010(3) -0.002(2) N1 0.054(4) 0.062(5) 0.057(5) -0.025(4) -0.019(3) -0.021(3) C1 0.035(3) 0.029(4) 0.051(4) -0.009(3) -0.020(3) 0.000(2) C2 0.036(3) 0.032(4) 0.049(4) -0.018(3) -0.014(3) 0.000(3) C3 0.037(3) 0.036(4) 0.045(4) -0.018(3) -0.017(3) -0.001(3) C4 0.031(3) 0.031(3) 0.045(4) -0.017(3) -0.012(3) -0.002(2) C5 0.039(3) 0.051(5) 0.043(4) -0.017(4) -0.015(3) -0.005(3) C6 0.040(3) 0.051(5) 0.048(4) -0.015(4) -0.020(3) -0.006(3) C7 0.030(3) 0.027(3) 0.049(4) -0.019(3) -0.013(3) 0.000(2) C8 0.033(3) 0.031(4) 0.050(4) -0.025(3) -0.013(3) 0.000(2) C9 0.036(3) 0.038(4) 0.053(4) -0.030(3) -0.007(3) -0.006(3) C10 0.029(3) 0.055(5) 0.057(5) -0.032(4) -0.008(3) -0.007(3) C11 0.037(3) 0.036(4) 0.061(5) -0.028(3) -0.018(3) 0.000(3) C12 0.035(3) 0.039(4) 0.047(4) -0.022(3) -0.010(3) -0.005(3) C13 0.026(3) 0.050(4) 0.046(4) -0.024(3) -0.004(3) -0.006(3) C14 0.030(3) 0.026(3) 0.050(4) -0.022(3) -0.010(3) 0.001(2) C15 0.052(4) 0.041(4) 0.052(4) -0.009(3) -0.025(3) -0.011(3) C16 0.053(4) 0.040(4) 0.061(5) -0.019(4) -0.019(4) -0.016(3) C17 0.034(3) 0.046(4) 0.047(4) -0.021(3) -0.011(3) -0.010(3) C18 0.059(4) 0.043(4) 0.054(5) -0.013(4) -0.029(4) -0.009(3) C19 0.055(4) 0.030(4) 0.058(5) -0.014(4) -0.025(4) -0.008(3) C20 0.042(4) 0.074(6) 0.062(5) -0.034(5) -0.013(4) -0.004(4) C21 0.059(5) 0.111(8) 0.062(6) -0.027(6) -0.030(4) -0.016(5) C22 0.045(4) 0.059(5) 0.087(6) -0.052(5) -0.006(4) -0.004(4) C23 0.052(4) 0.043(5) 0.075(6) -0.024(4) -0.006(4) -0.010(3) C24 0.45(4) 0.076(12) 0.127(16) -0.013(11) -0.11(2) -0.021(17) C25 0.21(2) 0.091(11) 0.054(7) -0.033(7) -0.018(10) -0.025(12) C26 0.093(9) 0.150(14) 0.069(7) -0.043(9) -0.014(7) -0.053(9) C27 0.127(14) 0.161(18) 0.084(10) -0.056(12) -0.039(9) 0.007(13) C28 0.17(2) 0.132(15) 0.119(14) -0.056(11) -0.035(14) -0.044(15) C29 0.167(18) 0.25(3) 0.089(11) -0.064(15) -0.008(12) -0.12(2) C30 0.079(8) 0.174(16) 0.069(8) -0.058(10) -0.009(6) -0.028(10) _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 C7 C4 1.525(8) . ? C7 C14 1.534(9) . ? C7 C8 1.538(9) . ? C8 C13 1.376(10) . ? C8 C9 1.389(8) . ? C10 C9 1.385(10) . ? C10 C11 1.387(10) . ? C10 C22 1.511(9) . ? C13 C12 1.373(10) . ? C2 C1 1.393(10) . ? C2 C3 1.399(9) . ? C2 C20 1.493(10) . ? C6 C1 1.380(10) . ? C6 C5 1.400(9) . ? C6 C21 1.507(11) . ? C14 C19 1.371(10) . ? C14 C15 1.373(10) . ? C4 C3 1.374(9) . ? C4 C5 1.391(10) . ? C11 O2 1.370(9) . ? C11 C12 1.398(9) . ? C1 O1 1.380(8) . ? C19 C18 1.413(10) . ? C12 C23 1.499(10) . ? C16 C17 1.376(11) . ? C16 C15 1.403(10) . ? C17 C18 1.365(10) . ? C17 N1 1.428(9) . ? C26 C27 1.28(2) . ? C26 C25 1.40(2) . ? C30 C25 1.38(2) . ? C30 C29 1.44(3) . ? C25 C24 1.38(2) . ? C27 C28 1.32(2) . ? C28 C29 1.29(2) . ? 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 C4 C7 C14 113.4(5) . . ? C4 C7 C8 112.1(5) . . ? C14 C7 C8 112.2(5) . . ? C13 C8 C9 117.9(6) . . ? C13 C8 C7 123.2(6) . . ? C9 C8 C7 118.9(6) . . ? C9 C10 C11 117.9(6) . . ? C9 C10 C22 120.4(7) . . ? C11 C10 C22 121.7(7) . . ? C12 C13 C8 122.4(6) . . ? C1 C2 C3 117.6(6) . . ? C1 C2 C20 120.7(6) . . ? C3 C2 C20 121.7(7) . . ? C10 C9 C8 122.1(7) . . ? C1 C6 C5 117.7(6) . . ? C1 C6 C21 121.4(6) . . ? C5 C6 C21 120.9(7) . . ? C19 C14 C15 117.9(7) . . ? C19 C14 C7 123.2(6) . . ? C15 C14 C7 118.8(6) . . ? C3 C4 C5 118.7(6) . . ? C3 C4 C7 124.0(6) . . ? C5 C4 C7 117.2(6) . . ? C4 C3 C2 121.8(7) . . ? O2 C11 C10 123.0(6) . . ? O2 C11 C12 115.6(7) . . ? C10 C11 C12 121.4(6) . . ? C6 C1 O1 116.8(6) . . ? C6 C1 C2 122.6(6) . . ? O1 C1 C2 120.6(6) . . ? C14 C19 C18 120.8(7) . . ? C4 C5 C6 121.5(7) . . ? C13 C12 C11 118.2(7) . . ? C13 C12 C23 122.4(6) . . ? C11 C12 C23 119.4(6) . . ? C17 C16 C15 119.9(7) . . ? C18 C17 C16 119.0(7) . . ? C18 C17 N1 121.7(7) . . ? C16 C17 N1 119.3(7) . . ? C17 C18 C19 120.6(7) . . ? C14 C15 C16 121.7(7) . . ? C27 C26 C25 121.0(16) . . ? C25 C30 C29 119.0(15) . . ? C30 C25 C24 124(3) . . ? C30 C25 C26 115.7(14) . . ? C24 C25 C26 121(3) . . ? C26 C27 C28 124.8(19) . . ? C29 C28 C27 119(2) . . ? C28 C29 C30 120.3(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 C4 C7 C8 C13 39.5(9) . . . . ? C14 C7 C8 C13 -89.5(7) . . . . ? C4 C7 C8 C9 -142.6(6) . . . . ? C14 C7 C8 C9 88.4(8) . . . . ? C9 C8 C13 C12 -1.8(10) . . . . ? C7 C8 C13 C12 176.1(6) . . . . ? C11 C10 C9 C8 0.2(10) . . . . ? C22 C10 C9 C8 -178.8(7) . . . . ? C13 C8 C9 C10 1.5(10) . . . . ? C7 C8 C9 C10 -176.5(6) . . . . ? C4 C7 C14 C19 -105.2(7) . . . . ? C8 C7 C14 C19 23.1(9) . . . . ? C4 C7 C14 C15 77.2(8) . . . . ? C8 C7 C14 C15 -154.6(6) . . . . ? C14 C7 C4 C3 33.3(9) . . . . ? C8 C7 C4 C3 -95.0(8) . . . . ? C14 C7 C4 C5 -146.5(6) . . . . ? C8 C7 C4 C5 85.2(8) . . . . ? C5 C4 C3 C2 -3.1(11) . . . . ? C7 C4 C3 C2 177.1(6) . . . . ? C1 C2 C3 C4 1.2(10) . . . . ? C20 C2 C3 C4 178.9(7) . . . . ? C9 C10 C11 O2 179.2(7) . . . . ? C22 C10 C11 O2 -1.8(11) . . . . ? C9 C10 C11 C12 -1.7(10) . . . . ? C22 C10 C11 C12 177.2(7) . . . . ? C5 C6 C1 O1 179.6(7) . . . . ? C21 C6 C1 O1 0.4(11) . . . . ? C5 C6 C1 C2 -2.3(11) . . . . ? C21 C6 C1 C2 178.5(8) . . . . ? C3 C2 C1 C6 1.6(11) . . . . ? C20 C2 C1 C6 -176.2(7) . . . . ? C3 C2 C1 O1 179.6(6) . . . . ? C20 C2 C1 O1 1.9(11) . . . . ? C15 C14 C19 C18 -0.7(11) . . . . ? C7 C14 C19 C18 -178.3(6) . . . . ? C3 C4 C5 C6 2.4(11) . . . . ? C7 C4 C5 C6 -177.8(7) . . . . ? C1 C6 C5 C4 0.2(11) . . . . ? C21 C6 C5 C4 179.5(8) . . . . ? C8 C13 C12 C11 0.3(11) . . . . ? C8 C13 C12 C23 -178.7(7) . . . . ? O2 C11 C12 C13 -179.4(6) . . . . ? C10 C11 C12 C13 1.5(10) . . . . ? O2 C11 C12 C23 -0.3(10) . . . . ? C10 C11 C12 C23 -179.4(7) . . . . ? C15 C16 C17 C18 2.0(11) . . . . ? C15 C16 C17 N1 -176.4(7) . . . . ? C16 C17 C18 C19 -2.1(11) . . . . ? N1 C17 C18 C19 176.2(7) . . . . ? C14 C19 C18 C17 1.5(12) . . . . ? C19 C14 C15 C16 0.6(10) . . . . ? C7 C14 C15 C16 178.3(6) . . . . ? C17 C16 C15 C14 -1.2(11) . . . . ? C29 C30 C25 C24 177.5(15) . . . . ? C29 C30 C25 C26 -2.8(19) . . . . ? C27 C26 C25 C30 0(2) . . . . ? C27 C26 C25 C24 179.5(15) . . . . ? C25 C26 C27 C28 3(3) . . . . ? C26 C27 C28 C29 -2(3) . . . . ? C27 C28 C29 C30 -1(3) . . . . ? C25 C30 C29 C28 4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.877 _diffrn_reflns_theta_full 30.72 _diffrn_measured_fraction_theta_full 0.877 _refine_diff_density_max 0.546 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.075 # Attachment 'D4OH.cif' data_jbb00105_0m _database_code_depnum_ccdc_archive 'CCDC 281631' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (Bis(4-hydroxy-3,5-dimethylphenyl)(4-hydroxyphenyl))methane _chemical_melting_point ? _chemical_formula_moiety 'C30 H32 O3' _chemical_formula_sum 'C30 H32 O3' _chemical_formula_weight 440.56 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.692(2) _cell_length_b 11.739(3) _cell_length_c 12.104(7) _cell_angle_alpha 112.155(3) _cell_angle_beta 101.102(4) _cell_angle_gamma 91.062(4) _cell_volume 1245.3 _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3262 _cell_measurement_theta_min 4.39 _cell_measurement_theta_max 26.70 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.074 _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 0.71073 _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 7748 _diffrn_reflns_av_R_equivalents 0.0128 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 26.75 _reflns_number_total 4364 _reflns_number_gt 3391 _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^)+(0.1142P)^2^+0.4088P] 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 4364 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.2065 _refine_ls_wR_factor_gt 0.1893 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.2695(2) 0.89981(15) 0.50692(14) 0.0634(6) Uani 1 1 d . . . O2 O 0.3719(2) 0.87524(15) 1.29964(14) 0.0586(5) Uani 1 1 d . . . O3 O 0.3481(3) 0.14763(14) 0.60696(16) 0.0619(5) Uani 1 1 d . . . H1O H 0.265(3) 0.975(3) 0.544(2) 0.058(7) Uiso 1 1 d . . . H2O H 0.315(5) 0.861(3) 1.339(3) 0.100(12) Uiso 1 1 d . . . H3O H 0.442(5) 0.154(3) 0.652(3) 0.090(11) Uiso 1 1 d . . . C1 C 0.2432(3) 0.83628(17) 0.57800(16) 0.0471(6) Uani 1 1 d . . . C2 C 0.3128(3) 0.7316(2) 0.56695(19) 0.0521(6) Uani 1 1 d . . . C3 C 0.2859(3) 0.6642(2) 0.63459(18) 0.0495(6) Uani 1 1 d . . . H3 H 0.3318 0.5938 0.6279 0.059 Uiso 1 1 calc R . . C4 C 0.1921(3) 0.69927(18) 0.71186(16) 0.0423(5) Uani 1 1 d . . . C5 C 0.1266(3) 0.80559(19) 0.72147(18) 0.0464(5) Uani 1 1 d . . . H5 H 0.0647 0.8309 0.7741 0.056 Uiso 1 1 calc R . . C6 C 0.1502(3) 0.87557(18) 0.65549(17) 0.0462(5) Uani 1 1 d . . . C7 C 0.1578(3) 0.62698(18) 0.78725(17) 0.0434(5) Uani 1 1 d . . . C8 C 0.2140(3) 0.69956(17) 0.92458(17) 0.0416(5) Uani 1 1 d . . . C9 C 0.3329(3) 0.78297(19) 0.97235(18) 0.0467(5) Uani 1 1 d . . . H9 H 0.3800 0.7994 0.9190 0.056 Uiso 1 1 calc R . . C10 C 0.3853(3) 0.84364(19) 1.09757(18) 0.0478(5) Uani 1 1 d . . . C11 C 0.3128(3) 0.81638(18) 1.17561(17) 0.0455(5) Uani 1 1 d . . . C12 C 0.1918(3) 0.73482(19) 1.13183(18) 0.0473(6) Uani 1 1 d . . . C13 C 0.1436(3) 0.67772(19) 1.00548(18) 0.0457(5) Uani 1 1 d . . . H13 H 0.0617 0.6233 0.9744 0.055 Uiso 1 1 calc R . . C14 C 0.4196(4) 0.6946(3) 0.4876(3) 0.0793(10) Uani 1 1 d . . . H14A H 0.3744 0.6779 0.4045 0.119 Uiso 1 1 calc R . . H14B H 0.4586 0.6217 0.4927 0.119 Uiso 1 1 calc R . . H14C H 0.4939 0.7605 0.5151 0.119 Uiso 1 1 calc R . . C15 C 0.0754(3) 0.9899(2) 0.6679(2) 0.0640(8) Uani 1 1 d . . . H15A H 0.1439 1.0606 0.6977 0.096 Uiso 1 1 calc R . . H15B H 0.0145 1.0011 0.7243 0.096 Uiso 1 1 calc R . . H15C H 0.0201 0.9808 0.5897 0.096 Uiso 1 1 calc R . . C16 C 0.5122(4) 0.9365(3) 1.1478(2) 0.0710(8) Uani 1 1 d . . . H16A H 0.4897 1.0121 1.2056 0.106 Uiso 1 1 calc R . . H16B H 0.5400 0.9520 1.0824 0.106 Uiso 1 1 calc R . . H16C H 0.5883 0.9051 1.1878 0.106 Uiso 1 1 calc R . . C17 C 0.1099(4) 0.7082(3) 1.2151(2) 0.0658(8) Uani 1 1 d . . . H17A H 0.1684 0.6714 1.2634 0.099 Uiso 1 1 calc R . . H17B H 0.0274 0.6523 1.1669 0.099 Uiso 1 1 calc R . . H17C H 0.0818 0.7839 1.2680 0.099 Uiso 1 1 calc R . . C18 C 0.2104(3) 0.49849(17) 0.74491(16) 0.0422(5) Uani 1 1 d . . . C19 C 0.3384(3) 0.4734(2) 0.79871(19) 0.0548(6) Uani 1 1 d . . . H19 H 0.3942 0.5360 0.8665 0.066 Uiso 1 1 calc R . . C20 C 0.3867(3) 0.3576(2) 0.7548(2) 0.0566(6) Uani 1 1 d . . . H20 H 0.4740 0.3433 0.7924 0.068 Uiso 1 1 calc R . . C21 C 0.3042(3) 0.26374(18) 0.65504(18) 0.0489(6) Uani 1 1 d . . . C22 C 0.1751(3) 0.2866(2) 0.6004(2) 0.0593(7) Uani 1 1 d . . . H22 H 0.1191 0.2238 0.5330 0.071 Uiso 1 1 calc R . . C23 C 0.1290(3) 0.4020(2) 0.6451(2) 0.0538(6) Uani 1 1 d . . . H23 H 0.0413 0.4159 0.6078 0.065 Uiso 1 1 calc R . . C24 C 0.2645(10) 0.3535(11) 0.0236(9) 0.236(6) Uani 1 1 d . . . H24A H 0.1970 0.3133 -0.0521 0.354 Uiso 1 1 calc R . . H24B H 0.3582 0.3507 0.0081 0.354 Uiso 1 1 calc R . . H24C H 0.2460 0.4380 0.0612 0.354 Uiso 1 1 calc R . . C25 C 0.2542(7) 0.2971(7) 0.0961(7) 0.172(3) Uani 1 1 d G . . C30 C 0.2760(8) 0.3689(7) 0.2203(8) 0.236(6) Uani 1 1 d G . . H30 H 0.3010 0.4536 0.2490 0.283 Uiso 1 1 calc R . . C29 C 0.2604(10) 0.3143(14) 0.3016(5) 0.394(15) Uani 1 1 d G . . H29 H 0.2750 0.3624 0.3847 0.472 Uiso 1 1 calc R . . C27 C 0.2231(11) 0.1878(14) 0.2586(11) 0.291(10) Uani 1 1 d G . . H27 H 0.2127 0.1512 0.3130 0.350 Uiso 1 1 calc R . . C28 C 0.2013(9) 0.1159(8) 0.1344(13) 0.395(15) Uani 1 1 d G . . H28 H 0.1763 0.0313 0.1056 0.474 Uiso 1 1 calc R . . C26 C 0.2169(7) 0.1706(7) 0.0531(7) 0.208(5) Uani 1 1 d G . . H26 H 0.2023 0.1225 -0.0300 0.249 Uiso 1 1 calc R . . 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 0.1110(19) 0.0415(8) 0.0430(8) 0.0177(7) 0.0264(9) 0.0014(8) O2 0.0760(16) 0.0621(10) 0.0393(8) 0.0192(7) 0.0170(8) 0.0050(9) O3 0.0784(18) 0.0388(8) 0.0654(10) 0.0152(7) 0.0193(10) 0.0034(8) C1 0.0681(19) 0.0401(9) 0.0311(8) 0.0137(7) 0.0072(9) -0.0021(10) C2 0.067(2) 0.0524(11) 0.0431(10) 0.0210(9) 0.0203(10) 0.0086(11) C3 0.0604(18) 0.0495(11) 0.0469(10) 0.0237(9) 0.0196(10) 0.0138(11) C4 0.0476(16) 0.0457(10) 0.0368(9) 0.0196(8) 0.0088(8) 0.0051(9) C5 0.0524(17) 0.0490(11) 0.0422(10) 0.0206(8) 0.0140(9) 0.0102(10) C6 0.0576(17) 0.0410(10) 0.0376(9) 0.0151(7) 0.0054(9) 0.0048(10) C7 0.0486(16) 0.0458(10) 0.0420(10) 0.0222(8) 0.0129(9) 0.0076(9) C8 0.0481(16) 0.0420(9) 0.0424(9) 0.0212(8) 0.0166(9) 0.0106(9) C9 0.0527(17) 0.0531(11) 0.0440(10) 0.0261(9) 0.0180(9) 0.0042(10) C10 0.0536(18) 0.0498(11) 0.0462(10) 0.0246(9) 0.0125(9) 0.0022(10) C11 0.0594(17) 0.0438(10) 0.0389(9) 0.0192(8) 0.0164(9) 0.0120(10) C12 0.0576(18) 0.0493(11) 0.0468(10) 0.0252(9) 0.0239(10) 0.0129(10) C13 0.0473(16) 0.0465(10) 0.0496(11) 0.0223(8) 0.0171(9) 0.0058(9) C14 0.107(3) 0.0810(17) 0.0813(18) 0.0460(15) 0.0588(19) 0.0330(19) C15 0.086(2) 0.0510(12) 0.0633(14) 0.0289(10) 0.0193(13) 0.0176(13) C16 0.075(3) 0.0823(17) 0.0545(13) 0.0299(12) 0.0081(12) -0.0208(15) C17 0.077(2) 0.0767(16) 0.0557(13) 0.0311(12) 0.0312(13) 0.0047(14) C18 0.0501(16) 0.0426(10) 0.0387(9) 0.0201(7) 0.0116(8) 0.0025(9) C19 0.062(2) 0.0455(11) 0.0464(11) 0.0103(8) 0.0016(10) 0.0068(11) C20 0.060(2) 0.0500(11) 0.0535(12) 0.0164(9) 0.0048(10) 0.0126(12) C21 0.0659(19) 0.0382(10) 0.0476(10) 0.0190(8) 0.0187(10) 0.0025(10) C22 0.066(2) 0.0473(11) 0.0537(12) 0.0126(9) 0.0025(11) -0.0096(11) C23 0.0507(19) 0.0541(12) 0.0542(12) 0.0225(9) 0.0030(10) -0.0013(11) C24 0.098(9) 0.423(16) 0.327(12) 0.285(13) 0.076(8) 0.076(10) C25 0.044(6) 0.286(10) 0.197(7) 0.110(8) 0.020(4) 0.016(6) C30 0.123(10) 0.285(11) 0.170(7) -0.041(8) -0.003(5) 0.034(9) C29 0.15(3) 0.51(3) 0.59(3) 0.32(3) 0.00(2) -0.01(2) C27 0.081(15) 0.53(3) 0.37(2) 0.274(19) 0.083(13) 0.060(16) C28 0.31(2) 0.43(2) 0.71(4) 0.37(3) 0.40(3) 0.26(2) C26 0.118(10) 0.175(7) 0.253(10) -0.016(7) 0.068(7) -0.012(6) _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 C1 C6 1.386(3) . ? C1 O1 1.387(2) . ? C1 C2 1.387(3) . ? C2 C3 1.389(3) . ? C2 C14 1.506(3) . ? C3 C4 1.386(3) . ? C4 C5 1.387(3) . ? C4 C7 1.534(3) . ? C5 C6 1.387(3) . ? C6 C15 1.508(3) . ? C7 C18 1.531(3) . ? C7 C8 1.533(3) . ? C8 C9 1.377(3) . ? C8 C13 1.389(3) . ? C9 C10 1.392(3) . ? C10 C11 1.401(3) . ? C10 C16 1.494(4) . ? C11 C12 1.382(4) . ? C11 O2 1.390(3) . ? C12 C13 1.395(3) . ? C12 C17 1.510(3) . ? C18 C19 1.378(3) . ? C18 C23 1.390(3) . ? C19 C20 1.387(3) . ? C20 C21 1.380(3) . ? C21 O3 1.377(3) . ? C21 C22 1.380(4) . ? C22 C23 1.376(3) . ? C24 C25 1.299(9) . ? C25 C30 1.3900 . ? C25 C26 1.3900 . ? C30 C29 1.3900 . ? C29 C27 1.3900 . ? C27 C28 1.3900 . ? C28 C26 1.3900 . ? 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 C6 C1 O1 121.10(19) . . ? C6 C1 C2 121.82(18) . . ? O1 C1 C2 117.1(2) . . ? C1 C2 C3 118.5(2) . . ? C1 C2 C14 120.94(19) . . ? C3 C2 C14 120.5(2) . . ? C4 C3 C2 121.56(19) . . ? C3 C4 C5 118.00(17) . . ? C3 C4 C7 123.41(17) . . ? C5 C4 C7 118.59(18) . . ? C6 C5 C4 122.35(19) . . ? C1 C6 C5 117.80(18) . . ? C1 C6 C15 121.70(19) . . ? C5 C6 C15 120.5(2) . . ? C18 C7 C8 111.28(15) . . ? C18 C7 C4 111.88(15) . . ? C8 C7 C4 111.88(17) . . ? C9 C8 C13 118.08(19) . . ? C9 C8 C7 123.48(17) . . ? C13 C8 C7 118.4(2) . . ? C8 C9 C10 122.37(18) . . ? C9 C10 C11 117.5(2) . . ? C9 C10 C16 121.64(19) . . ? C11 C10 C16 120.8(2) . . ? C12 C11 O2 122.31(18) . . ? C12 C11 C10 122.11(19) . . ? O2 C11 C10 115.6(2) . . ? C11 C12 C13 117.77(18) . . ? C11 C12 C17 122.6(2) . . ? C13 C12 C17 119.6(2) . . ? C8 C13 C12 122.1(2) . . ? C19 C18 C23 117.33(19) . . ? C19 C18 C7 123.1(2) . . ? C23 C18 C7 119.5(2) . . ? C18 C19 C20 122.0(2) . . ? C21 C20 C19 119.5(2) . . ? O3 C21 C22 118.8(2) . . ? O3 C21 C20 121.8(2) . . ? C22 C21 C20 119.5(2) . . ? C23 C22 C21 120.2(2) . . ? C22 C23 C18 121.5(2) . . ? C24 C25 C30 117.5(8) . . ? C24 C25 C26 122.4(8) . . ? C30 C25 C26 120.0 . . ? C25 C30 C29 120.0 . . ? C27 C29 C30 120.0 . . ? C29 C27 C28 120.0 . . ? C27 C28 C26 120.0 . . ? C28 C26 C25 120.0 . . ? 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 C6 C1 C2 C3 1.0(4) . . . . ? O1 C1 C2 C3 -178.4(2) . . . . ? C6 C1 C2 C14 -176.5(3) . . . . ? O1 C1 C2 C14 4.2(4) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C14 C2 C3 C4 177.4(3) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C2 C3 C4 C7 179.3(2) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? C7 C4 C5 C6 -179.2(2) . . . . ? O1 C1 C6 C5 178.5(2) . . . . ? C2 C1 C6 C5 -0.8(4) . . . . ? O1 C1 C6 C15 -1.1(4) . . . . ? C2 C1 C6 C15 179.6(2) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C4 C5 C6 C15 179.4(2) . . . . ? C3 C4 C7 C18 -13.5(3) . . . . ? C5 C4 C7 C18 166.7(2) . . . . ? C3 C4 C7 C8 112.1(2) . . . . ? C5 C4 C7 C8 -67.6(3) . . . . ? C18 C7 C8 C9 95.8(2) . . . . ? C4 C7 C8 C9 -30.2(3) . . . . ? C18 C7 C8 C13 -82.3(2) . . . . ? C4 C7 C8 C13 151.70(18) . . . . ? C13 C8 C9 C10 1.1(3) . . . . ? C7 C8 C9 C10 -177.07(18) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C8 C9 C10 C16 -178.2(2) . . . . ? C9 C10 C11 C12 -1.5(3) . . . . ? C16 C10 C11 C12 177.2(2) . . . . ? C9 C10 C11 O2 177.53(18) . . . . ? C16 C10 C11 O2 -3.8(3) . . . . ? O2 C11 C12 C13 -178.04(17) . . . . ? C10 C11 C12 C13 0.9(3) . . . . ? O2 C11 C12 C17 3.3(3) . . . . ? C10 C11 C12 C17 -177.8(2) . . . . ? C9 C8 C13 C12 -1.7(3) . . . . ? C7 C8 C13 C12 176.55(17) . . . . ? C11 C12 C13 C8 0.7(3) . . . . ? C17 C12 C13 C8 179.4(2) . . . . ? C8 C7 C18 C19 -30.6(3) . . . . ? C4 C7 C18 C19 95.3(2) . . . . ? C8 C7 C18 C23 151.6(2) . . . . ? C4 C7 C18 C23 -82.5(3) . . . . ? C23 C18 C19 C20 1.1(4) . . . . ? C7 C18 C19 C20 -176.8(2) . . . . ? C18 C19 C20 C21 -0.6(4) . . . . ? C19 C20 C21 O3 179.1(2) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? O3 C21 C22 C23 -179.2(2) . . . . ? C20 C21 C22 C23 -0.1(4) . . . . ? C21 C22 C23 C18 0.6(4) . . . . ? C19 C18 C23 C22 -1.1(4) . . . . ? C7 C18 C23 C22 176.9(2) . . . . ? C24 C25 C30 C29 177.3(6) . . . . ? C26 C25 C30 C29 0.0 . . . . ? C25 C30 C29 C27 0.0 . . . . ? C30 C29 C27 C28 0.0 . . . . ? C29 C27 C28 C26 0.0 . . . . ? C27 C28 C26 C25 0.0 . . . . ? C24 C25 C26 C28 -177.2(7) . . . . ? C30 C25 C26 C28 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.822 _diffrn_reflns_theta_full 26.75 _diffrn_measured_fraction_theta_full 0.822 _refine_diff_density_max 0.485 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.042 # Attachment 'D4NIC.cif' data_rj007_1_0m _database_code_depnum_ccdc_archive 'CCDC 281632' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Bis(((4-hydroxy-3,5-dimethylphenyl)methyl)phenyl)nicotinamide _chemical_melting_point ? _chemical_formula_moiety 'C29 H28 N2 O3' _chemical_formula_sum 'C29 H28 N2 O3' _chemical_formula_weight 452.53 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' _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 5.331(4) _cell_length_b 14.537(13) _cell_length_c 15.166(14) _cell_angle_alpha 85.576(6) _cell_angle_beta 88.042(6) _cell_angle_gamma 85.168(6) _cell_volume 1167.36(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1986 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.084 _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 0.71073 _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 20880 _diffrn_reflns_av_R_equivalents 0.1012 _diffrn_reflns_av_sigmaI/netI 0.1612 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 35.40 _reflns_number_total 9347 _reflns_number_gt 3260 _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^)+(0.2000P)^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 9347 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1312 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 0.872 _refine_ls_restrained_S_all 0.872 _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 -0.0941(5) 0.8034(2) -0.06952(15) 0.0664(7) Uani 1 1 d . . . O3 O -0.0952(4) 0.8820(2) 0.55506(15) 0.0666(8) Uani 1 1 d . . . O2 O 0.2676(6) 0.25801(17) 0.32457(19) 0.0777(8) Uani 1 1 d . . . N1 N 0.3260(4) 0.85887(17) 0.53227(15) 0.0461(6) Uani 1 1 d . . . H1N H 0.4691 0.8714 0.5508 0.055 Uiso 1 1 calc R . . N2 N 0.0237(6) 0.9774(2) 0.80131(18) 0.0641(8) Uani 1 1 d . . . C1 C 0.0331(6) 0.7645(2) 0.00330(18) 0.0471(7) Uani 1 1 d . . . C2 C 0.2187(6) 0.8100(2) 0.04229(19) 0.0490(7) Uani 1 1 d . . . C3 C 0.3334(6) 0.7656(2) 0.11599(19) 0.0474(7) Uani 1 1 d . . . C4 C 0.2743(5) 0.67914(19) 0.15282(16) 0.0390(6) Uani 1 1 d . . . C5 C 0.0926(5) 0.6353(2) 0.11148(18) 0.0440(6) Uani 1 1 d . . . C6 C -0.0277(6) 0.6765(2) 0.03641(19) 0.0495(7) Uani 1 1 d . . . C7 C 0.4150(5) 0.63694(19) 0.23410(17) 0.0382(6) Uani 1 1 d . . . H7 H 0.5943 0.6362 0.2174 0.046 Uiso 1 1 calc R . . C8 C 0.3669(5) 0.53700(19) 0.25984(17) 0.0398(6) Uani 1 1 d . . . C9 C 0.5088(6) 0.4663(2) 0.22060(19) 0.0458(7) Uani 1 1 d . . . H9 H 0.6321 0.4817 0.1785 0.055 Uiso 1 1 calc R . . C10 C 0.4746(6) 0.3731(2) 0.2416(2) 0.0509(7) Uani 1 1 d . . . C11 C 0.2900(6) 0.3518(2) 0.3031(2) 0.0517(8) Uani 1 1 d . . . C12 C 0.1371(6) 0.4195(2) 0.3443(2) 0.0507(7) Uani 1 1 d . . . C13 C 0.1810(5) 0.5126(2) 0.32166(19) 0.0449(7) Uani 1 1 d . . . C14 C 0.2979(9) 0.9024(3) 0.0042(3) 0.0710(11) Uani 1 1 d . . . H14A H 0.4041 0.9268 0.0450 0.106 Uiso 1 1 calc R . . H14B H 0.1513 0.9444 -0.0058 0.106 Uiso 1 1 calc R . . H14C H 0.3888 0.8946 -0.0508 0.106 Uiso 1 1 calc R . . C15 C -0.2156(7) 0.6270(3) -0.0094(2) 0.0656(10) Uani 1 1 d . . . H15A H -0.2405 0.5690 0.0231 0.098 Uiso 1 1 calc R . . H15B H -0.1537 0.6158 -0.0681 0.098 Uiso 1 1 calc R . . H15C H -0.3727 0.6644 -0.0125 0.098 Uiso 1 1 calc R . . C16 C 0.6402(9) 0.2976(3) 0.1993(3) 0.0733(11) Uani 1 1 d . . . H16A H 0.7473 0.2650 0.2430 0.110 Uiso 1 1 calc R . . H16B H 0.7418 0.3248 0.1524 0.110 Uiso 1 1 calc R . . H16C H 0.5363 0.2551 0.1757 0.110 Uiso 1 1 calc R . . C17 C -0.0682(7) 0.3970(3) 0.4106(3) 0.0707(11) Uani 1 1 d . . . H17A H -0.1669 0.3520 0.3886 0.106 Uiso 1 1 calc R . . H17B H -0.1740 0.4522 0.4205 0.106 Uiso 1 1 calc R . . H17C H 0.0051 0.3724 0.4653 0.106 Uiso 1 1 calc R . . C18 C 0.3782(5) 0.69694(18) 0.31209(16) 0.0358(5) Uani 1 1 d . . . C19 C 0.5578(6) 0.6891(3) 0.3761(2) 0.0578(9) Uani 1 1 d . . . C20 C 0.5369(6) 0.7411(3) 0.4482(2) 0.0593(9) Uani 1 1 d . . . C21 C 0.3319(5) 0.80418(19) 0.45865(17) 0.0397(6) Uani 1 1 d . . . C22 C 0.1490(6) 0.8136(2) 0.39571(19) 0.0462(7) Uani 1 1 d . . . C23 C 0.1733(5) 0.7600(2) 0.32398(18) 0.0443(7) Uani 1 1 d . . . C24 C 0.1204(5) 0.8932(2) 0.57607(18) 0.0412(6) Uani 1 1 d . . . C25 C 0.1650(5) 0.94423(19) 0.65455(17) 0.0394(6) Uani 1 1 d . . . C26 C 0.0053(6) 0.9347(2) 0.7278(2) 0.0510(7) Uani 1 1 d . . . C27 C 0.2071(7) 1.0358(3) 0.8009(2) 0.0571(8) Uani 1 1 d . . . C28 C 0.3768(6) 1.0490(3) 0.7325(2) 0.0555(8) Uani 1 1 d . . . C29 C 0.3588(6) 1.0016(2) 0.6582(2) 0.0489(7) Uani 1 1 d . . . H1 H -0.0139 0.8441 -0.0945 0.100 Uiso 1 1 calc R . . H2 H 0.1488 0.2517 0.3597 0.117 Uiso 1 1 calc R . . H3 H 0.469(7) 0.795(2) 0.146(2) 0.059(9) Uiso 1 1 d . . . H5 H 0.054(6) 0.573(2) 0.135(2) 0.051(9) Uiso 1 1 d . . . H13 H 0.072(6) 0.562(2) 0.351(2) 0.044(8) Uiso 1 1 d . . . H20 H 0.655(6) 0.732(2) 0.496(2) 0.056(9) Uiso 1 1 d . . . H19 H 0.692(6) 0.643(2) 0.376(2) 0.050(9) Uiso 1 1 d . . . H22 H 0.016(6) 0.855(2) 0.402(2) 0.052(9) Uiso 1 1 d . . . H23 H 0.049(7) 0.762(2) 0.280(2) 0.057(9) Uiso 1 1 d . . . H27 H 0.226(8) 1.063(3) 0.854(3) 0.074(11) Uiso 1 1 d . . . H29 H 0.465(7) 1.008(2) 0.612(2) 0.059(10) Uiso 1 1 d . . . H28 H 0.502(9) 1.093(3) 0.739(3) 0.088(13) Uiso 1 1 d . . . H26 H -0.123(7) 0.893(2) 0.731(2) 0.059(10) 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 C16 0.095(3) 0.053(2) 0.072(2) -0.0151(18) -0.007(2) 0.006(2) C7 0.0410(12) 0.0381(14) 0.0359(12) -0.0042(10) 0.0017(10) -0.0064(11) C4 0.0458(13) 0.0411(15) 0.0306(12) -0.0048(10) 0.0009(11) -0.0066(11) C8 0.0421(13) 0.0410(15) 0.0376(13) -0.0029(11) -0.0035(11) -0.0104(11) C9 0.0531(15) 0.0438(16) 0.0415(14) -0.0052(12) -0.0025(12) -0.0073(13) C5 0.0458(14) 0.0523(18) 0.0354(13) -0.0031(12) 0.0025(11) -0.0143(13) C12 0.0497(15) 0.059(2) 0.0451(15) 0.0071(14) -0.0086(13) -0.0215(14) C3 0.0623(17) 0.0450(17) 0.0370(13) -0.0050(12) -0.0026(13) -0.0148(14) C6 0.0464(15) 0.064(2) 0.0393(14) -0.0086(13) 0.0026(12) -0.0085(14) C13 0.0438(14) 0.0473(17) 0.0432(15) 0.0032(12) 0.0004(12) -0.0074(13) C1 0.0494(15) 0.0580(19) 0.0330(13) -0.0028(12) 0.0016(12) 0.0001(13) C11 0.0679(19) 0.0404(16) 0.0500(16) -0.0014(13) -0.0180(15) -0.0188(14) C2 0.0598(17) 0.0473(17) 0.0398(14) -0.0021(12) 0.0040(13) -0.0077(14) C10 0.0642(18) 0.0443(17) 0.0461(16) -0.0070(13) -0.0120(14) -0.0074(14) C15 0.0604(19) 0.087(3) 0.0528(18) -0.0074(18) -0.0132(16) -0.0217(18) C17 0.0566(19) 0.080(3) 0.075(2) 0.021(2) -0.0012(17) -0.0273(18) C14 0.096(3) 0.056(2) 0.061(2) 0.0132(17) -0.010(2) -0.020(2) C18 0.0380(12) 0.0364(14) 0.0344(12) -0.0045(10) 0.0002(10) -0.0095(10) N1 0.0414(11) 0.0564(16) 0.0429(12) -0.0179(11) -0.0059(10) -0.0038(10) C21 0.0403(12) 0.0428(15) 0.0376(13) -0.0080(11) 0.0000(11) -0.0086(11) C22 0.0464(14) 0.0500(18) 0.0414(14) -0.0079(13) -0.0072(12) 0.0070(13) C23 0.0454(14) 0.0526(17) 0.0352(13) -0.0072(12) -0.0097(11) 0.0011(12) C20 0.0499(16) 0.077(2) 0.0541(18) -0.0287(17) -0.0192(15) 0.0077(15) N2 0.0752(19) 0.081(2) 0.0418(13) -0.0177(13) 0.0099(13) -0.0305(16) C19 0.0446(15) 0.068(2) 0.063(2) -0.0267(17) -0.0137(14) 0.0115(15) C25 0.0434(13) 0.0386(14) 0.0373(13) -0.0039(11) -0.0024(11) -0.0080(11) C24 0.0458(14) 0.0443(15) 0.0368(13) -0.0086(11) 0.0028(11) -0.0192(12) C29 0.0502(15) 0.0560(19) 0.0441(15) -0.0120(13) 0.0045(13) -0.0202(14) C26 0.0549(16) 0.0584(19) 0.0434(15) -0.0105(13) 0.0086(13) -0.0245(15) C28 0.0567(17) 0.061(2) 0.0539(18) -0.0135(15) -0.0025(15) -0.0232(16) C27 0.070(2) 0.063(2) 0.0425(16) -0.0148(15) -0.0048(15) -0.0202(17) O1 0.0672(15) 0.0810(19) 0.0490(13) 0.0086(12) -0.0104(11) -0.0036(13) O3 0.0444(11) 0.108(2) 0.0561(13) -0.0354(14) 0.0114(10) -0.0356(12) O2 0.114(2) 0.0462(14) 0.0767(19) 0.0052(12) -0.0155(16) -0.0297(15) _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 C16 C10 1.517(5) . ? C7 C8 1.516(4) . ? C7 C18 1.521(4) . ? C7 C4 1.525(4) . ? C4 C3 1.392(4) . ? C4 C5 1.395(4) . ? C8 C9 1.383(4) . ? C8 C13 1.390(4) . ? C9 C10 1.394(4) . ? C5 C6 1.395(4) . ? C12 C11 1.396(5) . ? C12 C13 1.407(4) . ? C12 C17 1.501(5) . ? C3 C2 1.382(4) . ? C6 C1 1.397(5) . ? C6 C15 1.500(4) . ? C1 O1 1.375(3) . ? C1 C2 1.406(4) . ? C11 C10 1.371(5) . ? C11 O2 1.392(4) . ? C2 C14 1.508(5) . ? C18 C19 1.378(4) . ? C18 C23 1.382(4) . ? N1 C24 1.342(4) . ? N1 C21 1.418(3) . ? C21 C20 1.379(4) . ? C21 C22 1.379(4) . ? C22 C23 1.383(4) . ? C20 C19 1.373(4) . ? N2 C26 1.327(4) . ? N2 C27 1.348(4) . ? C25 C26 1.382(4) . ? C25 C29 1.387(4) . ? C25 C24 1.487(4) . ? C24 O3 1.230(3) . ? C29 C28 1.375(4) . ? C28 C27 1.366(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C7 C18 112.2(2) . . ? C8 C7 C4 114.1(2) . . ? C18 C7 C4 112.6(2) . . ? C3 C4 C5 117.5(3) . . ? C3 C4 C7 118.6(2) . . ? C5 C4 C7 123.9(3) . . ? C9 C8 C13 117.7(3) . . ? C9 C8 C7 120.0(2) . . ? C13 C8 C7 122.3(3) . . ? C8 C9 C10 122.8(3) . . ? C4 C5 C6 121.5(3) . . ? C11 C12 C13 117.5(3) . . ? C11 C12 C17 123.0(3) . . ? C13 C12 C17 119.5(3) . . ? C2 C3 C4 123.4(3) . . ? C5 C6 C1 118.8(3) . . ? C5 C6 C15 120.9(3) . . ? C1 C6 C15 120.2(3) . . ? C8 C13 C12 121.7(3) . . ? O1 C1 C6 116.9(3) . . ? O1 C1 C2 121.9(3) . . ? C6 C1 C2 121.2(3) . . ? C10 C11 O2 116.1(3) . . ? C10 C11 C12 122.5(3) . . ? O2 C11 C12 121.3(3) . . ? C3 C2 C1 117.5(3) . . ? C3 C2 C14 120.5(3) . . ? C1 C2 C14 121.9(3) . . ? C11 C10 C9 117.8(3) . . ? C11 C10 C16 121.1(3) . . ? C9 C10 C16 121.1(3) . . ? C19 C18 C23 116.7(2) . . ? C19 C18 C7 119.1(2) . . ? C23 C18 C7 124.2(2) . . ? C24 N1 C21 126.8(2) . . ? C20 C21 C22 118.8(3) . . ? C20 C21 N1 117.8(2) . . ? C22 C21 N1 123.4(3) . . ? C21 C22 C23 119.8(3) . . ? C18 C23 C22 122.2(2) . . ? C19 C20 C21 120.3(3) . . ? C26 N2 C27 116.0(3) . . ? C20 C19 C18 122.2(3) . . ? C26 C25 C29 117.9(3) . . ? C26 C25 C24 118.7(2) . . ? C29 C25 C24 123.4(3) . . ? O3 C24 N1 123.0(2) . . ? O3 C24 C25 120.6(3) . . ? N1 C24 C25 116.4(2) . . ? C28 C29 C25 118.8(3) . . ? N2 C26 C25 124.4(3) . . ? C27 C28 C29 118.7(3) . . ? N2 C27 C28 124.1(3) . . ? 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 C8 C7 C4 C3 -170.7(2) . . . . ? C18 C7 C4 C3 60.0(3) . . . . ? C8 C7 C4 C5 7.8(4) . . . . ? C18 C7 C4 C5 -121.5(3) . . . . ? C18 C7 C8 C9 -144.7(2) . . . . ? C4 C7 C8 C9 85.7(3) . . . . ? C18 C7 C8 C13 36.0(3) . . . . ? C4 C7 C8 C13 -93.5(3) . . . . ? C13 C8 C9 C10 -1.0(4) . . . . ? C7 C8 C9 C10 179.8(2) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C7 C4 C5 C6 -179.0(3) . . . . ? C5 C4 C3 C2 1.2(5) . . . . ? C7 C4 C3 C2 179.7(3) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? C4 C5 C6 C15 177.6(3) . . . . ? C9 C8 C13 C12 0.2(4) . . . . ? C7 C8 C13 C12 179.4(2) . . . . ? C11 C12 C13 C8 0.8(4) . . . . ? C17 C12 C13 C8 -179.3(3) . . . . ? C5 C6 C1 O1 -178.5(3) . . . . ? C15 C6 C1 O1 2.7(4) . . . . ? C5 C6 C1 C2 2.3(4) . . . . ? C15 C6 C1 C2 -176.4(3) . . . . ? C13 C12 C11 C10 -1.1(4) . . . . ? C17 C12 C11 C10 179.0(3) . . . . ? C13 C12 C11 O2 176.9(3) . . . . ? C17 C12 C11 O2 -3.0(5) . . . . ? C4 C3 C2 C1 0.0(5) . . . . ? C4 C3 C2 C14 -178.1(3) . . . . ? O1 C1 C2 C3 179.2(3) . . . . ? C6 C1 C2 C3 -1.8(4) . . . . ? O1 C1 C2 C14 -2.8(5) . . . . ? C6 C1 C2 C14 176.3(3) . . . . ? O2 C11 C10 C9 -177.8(3) . . . . ? C12 C11 C10 C9 0.4(4) . . . . ? O2 C11 C10 C16 0.8(4) . . . . ? C12 C11 C10 C16 178.9(3) . . . . ? C8 C9 C10 C11 0.7(4) . . . . ? C8 C9 C10 C16 -177.9(3) . . . . ? C8 C7 C18 C19 74.2(3) . . . . ? C4 C7 C18 C19 -155.5(3) . . . . ? C8 C7 C18 C23 -105.6(3) . . . . ? C4 C7 C18 C23 24.7(4) . . . . ? C24 N1 C21 C20 -150.0(3) . . . . ? C24 N1 C21 C22 32.6(5) . . . . ? C20 C21 C22 C23 0.2(5) . . . . ? N1 C21 C22 C23 177.5(3) . . . . ? C19 C18 C23 C22 0.7(5) . . . . ? C7 C18 C23 C22 -179.5(3) . . . . ? C21 C22 C23 C18 -0.7(5) . . . . ? C22 C21 C20 C19 0.3(5) . . . . ? N1 C21 C20 C19 -177.2(3) . . . . ? C21 C20 C19 C18 -0.2(6) . . . . ? C23 C18 C19 C20 -0.3(5) . . . . ? C7 C18 C19 C20 179.9(3) . . . . ? C21 N1 C24 O3 -1.6(5) . . . . ? C21 N1 C24 C25 176.7(3) . . . . ? C26 C25 C24 O3 35.7(4) . . . . ? C29 C25 C24 O3 -144.1(3) . . . . ? C26 C25 C24 N1 -142.6(3) . . . . ? C29 C25 C24 N1 37.6(4) . . . . ? C26 C25 C29 C28 -2.7(5) . . . . ? C24 C25 C29 C28 177.1(3) . . . . ? C27 N2 C26 C25 2.4(5) . . . . ? C29 C25 C26 N2 0.6(5) . . . . ? C24 C25 C26 N2 -179.2(3) . . . . ? C25 C29 C28 C27 1.8(5) . . . . ? C26 N2 C27 C28 -3.4(6) . . . . ? C29 C28 C27 N2 1.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.881 _diffrn_reflns_theta_full 35.40 _diffrn_measured_fraction_theta_full 0.881 _refine_diff_density_max 0.547 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.114