# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email jacobsa@cput.ac.za _publ_contact_author_name 'Ayesha Jacobs' loop_ _publ_author_name 'Ayesha Jacobs' 'Luigi Nassimbeni' 'Nothemba Silwana' data_c:\H8DMA_a _database_code_depnum_ccdc_archive 'CCDC 828177' #TrackingRef '- HDMA_a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1, 4-bis (diphenylhydroxymethyl) benzene dimethylacetamide clathrate ; _chemical_formula_sum 'C40 H44 N2 O4' _chemical_formula_weight 616.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2630(6) _cell_length_b 16.4363(8) _cell_length_c 17.4733(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3234.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4901 _cell_measurement_theta_min 0.31 _cell_measurement_theta_max 30.53 _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(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 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 12767 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 30.53 _reflns_number_total 4901 _reflns_number_gt 3766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0655P)^2^+0.7170P] 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 4901 _refine_ls_number_parameters 273 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.065 _refine_ls_shift/su_mean 0.002 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 0.21390(7) 0.03867(5) 0.59664(5) 0.02778(18) Uani 1 1 d D . . C1 C 0.29185(9) -0.03015(6) 0.59913(6) 0.0207(2) Uani 1 1 d . . . C2 C 0.32159(9) -0.04982(6) 0.68296(6) 0.0220(2) Uani 1 1 d . . . C3 C 0.41473(10) -0.01004(7) 0.72042(7) 0.0277(2) Uani 1 1 d . . . H3 H 0.4620 0.0279 0.6930 0.033 Uiso 1 1 calc R . . C4 C 0.43945(10) -0.02500(8) 0.79710(7) 0.0320(3) Uani 1 1 d . . . H4 H 0.5039 0.0020 0.8213 0.038 Uiso 1 1 calc R . . C5 C 0.37014(11) -0.07916(8) 0.83819(7) 0.0323(3) Uani 1 1 d . . . H5 H 0.3871 -0.0898 0.8905 0.039 Uiso 1 1 calc R . . C6 C 0.27578(11) -0.11778(8) 0.80239(7) 0.0318(3) Uani 1 1 d . . . H6 H 0.2273 -0.1544 0.8306 0.038 Uiso 1 1 calc R . . C7 C 0.25153(10) -0.10330(7) 0.72547(6) 0.0274(2) Uani 1 1 d . . . H7 H 0.1866 -0.1301 0.7017 0.033 Uiso 1 1 calc R . . C8 C 0.22666(9) -0.10030(6) 0.55903(6) 0.0218(2) Uani 1 1 d . . . C9 C 0.27398(10) -0.17864(7) 0.55946(7) 0.0280(2) Uani 1 1 d . . . H9 H 0.3457 -0.1889 0.5863 0.034 Uiso 1 1 calc R . . C10 C 0.21772(12) -0.24193(8) 0.52115(8) 0.0341(3) Uani 1 1 d . . . H10 H 0.2505 -0.2952 0.5224 0.041 Uiso 1 1 calc R . . C11 C 0.11333(12) -0.22709(8) 0.48097(7) 0.0351(3) Uani 1 1 d . . . H11 H 0.0748 -0.2701 0.4545 0.042 Uiso 1 1 calc R . . C12 C 0.06572(11) -0.14960(8) 0.47964(7) 0.0338(3) Uani 1 1 d . . . H12 H -0.0055 -0.1394 0.4522 0.041 Uiso 1 1 calc R . . C13 C 0.12203(9) -0.08634(8) 0.51854(6) 0.0272(2) Uani 1 1 d . . . H13 H 0.0887 -0.0332 0.5174 0.033 Uiso 1 1 calc R . . C14 C 0.40276(8) -0.01287(6) 0.55004(6) 0.02000(19) Uani 1 1 d . . . C15 C 0.51018(9) -0.05378(6) 0.56036(6) 0.0223(2) Uani 1 1 d . . . H15 H 0.5182 -0.0911 0.6016 0.027 Uiso 1 1 calc R . . C16 C 0.39418(9) 0.04091(6) 0.48865(6) 0.0221(2) Uani 1 1 d . . . H16 H 0.3219 0.0693 0.4801 0.027 Uiso 1 1 calc R . . O1G O 0.1617(3) 0.1625(3) 0.68878(19) 0.0542(12) Uani 0.503(3) 1 d PD A 1 C1GA C 0.15252(17) 0.15799(13) 0.77056(13) 0.0293(6) Uani 0.497(3) 1 d PD A 2 C2GA C 0.2064(5) 0.1102(5) 0.8311(4) 0.0355(18) Uani 0.497(3) 1 d PD A 2 H2G1 H 0.1728 0.0552 0.8307 0.053 Uiso 0.497(3) 1 calc PR A 2 H2G2 H 0.1904 0.1360 0.8806 0.053 Uiso 0.497(3) 1 calc PR A 2 H2G3 H 0.2923 0.1072 0.8229 0.053 Uiso 0.497(3) 1 calc PR A 2 N3GA N 0.04946(15) 0.19812(12) 0.78145(11) 0.0300(6) Uani 0.497(3) 1 d PD A 2 C4GA C -0.0030(6) 0.2420(5) 0.7199(4) 0.058(3) Uani 0.503(3) 1 d PD A 1 H4G1 H 0.0156 0.2974 0.7368 0.088 Uiso 0.503(3) 1 calc PR A 1 H4G2 H -0.0759 0.2234 0.7450 0.088 Uiso 0.503(3) 1 calc PR A 1 H4G3 H -0.0143 0.2415 0.6643 0.088 Uiso 0.503(3) 1 calc PR A 1 C5GA C -0.0082(4) 0.2083(3) 0.85503(15) 0.0433(9) Uani 0.497(3) 1 d PD A 2 H5G1 H 0.0269 0.1707 0.8922 0.065 Uiso 0.497(3) 1 calc PR A 2 H5G2 H -0.0932 0.1968 0.8498 0.065 Uiso 0.497(3) 1 calc PR A 2 H5G3 H 0.0027 0.2644 0.8728 0.065 Uiso 0.497(3) 1 calc PR A 2 C1GB C 0.0940(2) 0.18805(13) 0.74002(9) 0.0304(6) Uani 0.503(3) 1 d PD A 1 N2GB N 0.10784(17) 0.16421(12) 0.81332(9) 0.0283(5) Uani 0.503(3) 1 d PD A 1 H1 H 0.2254(9) 0.0771(7) 0.6390(6) 0.058(5) Uiso 1 1 d D . . O2 O 0.2005(4) 0.1586(3) 0.70614(15) 0.0453(10) Uani 0.497(3) 1 d PD A 2 C17 C 0.2045(7) 0.1126(6) 0.8388(5) 0.051(3) Uani 0.503(3) 1 d PD A 1 H17A H 0.2397 0.0849 0.7946 0.076 Uiso 0.503(3) 1 calc PR A 1 H17B H 0.1741 0.0721 0.8750 0.076 Uiso 0.503(3) 1 calc PR A 1 H17C H 0.2650 0.1460 0.8641 0.076 Uiso 0.503(3) 1 calc PR A 1 C18 C -0.0084(5) 0.2439(4) 0.7211(2) 0.0321(18) Uani 0.497(3) 1 d PD A 2 H18A H 0.0266 0.2292 0.6716 0.048 Uiso 0.497(3) 1 calc PR A 2 H18B H 0.0026 0.3022 0.7301 0.048 Uiso 0.497(3) 1 calc PR A 2 H18C H -0.0934 0.2312 0.7207 0.048 Uiso 0.497(3) 1 calc PR A 2 C19 C 0.0331(4) 0.1939(3) 0.87491(18) 0.0432(9) Uani 0.503(3) 1 d PD A 1 H19A H 0.0315 0.2535 0.8739 0.065 Uiso 0.503(3) 1 calc PR A 1 H19B H 0.0650 0.1754 0.9241 0.065 Uiso 0.503(3) 1 calc PR A 1 H19C H -0.0477 0.1729 0.8684 0.065 Uiso 0.503(3) 1 calc PR A 1 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 0.0275(4) 0.0258(4) 0.0301(4) -0.0048(3) -0.0007(3) 0.0080(3) C1 0.0202(4) 0.0198(4) 0.0221(5) -0.0015(4) 0.0004(3) 0.0014(4) C2 0.0213(4) 0.0234(5) 0.0212(5) -0.0031(4) 0.0008(4) 0.0010(4) C3 0.0261(5) 0.0304(5) 0.0266(5) -0.0039(5) 0.0002(4) -0.0050(4) C4 0.0269(5) 0.0411(7) 0.0279(6) -0.0085(5) -0.0042(4) -0.0007(5) C5 0.0333(6) 0.0416(7) 0.0219(5) -0.0017(5) -0.0022(4) 0.0053(5) C6 0.0338(6) 0.0368(6) 0.0250(6) 0.0025(5) 0.0034(4) -0.0018(5) C7 0.0256(5) 0.0321(6) 0.0244(5) -0.0015(4) 0.0007(4) -0.0044(4) C8 0.0214(4) 0.0250(5) 0.0191(4) -0.0008(4) 0.0018(3) -0.0035(4) C9 0.0290(5) 0.0253(5) 0.0298(6) -0.0029(4) -0.0030(4) -0.0015(4) C10 0.0434(7) 0.0254(6) 0.0335(6) -0.0048(5) -0.0004(5) -0.0065(5) C11 0.0427(7) 0.0368(6) 0.0260(6) -0.0037(5) -0.0016(5) -0.0168(5) C12 0.0297(5) 0.0449(7) 0.0268(6) -0.0006(5) -0.0056(4) -0.0097(5) C13 0.0234(5) 0.0322(6) 0.0258(5) 0.0001(5) -0.0017(4) -0.0022(4) C14 0.0211(4) 0.0181(4) 0.0208(4) -0.0029(4) 0.0003(3) -0.0015(3) C15 0.0246(5) 0.0200(5) 0.0223(5) 0.0024(4) 0.0003(4) 0.0014(4) C16 0.0214(4) 0.0204(5) 0.0246(5) -0.0003(4) -0.0007(4) 0.0025(4) O1G 0.084(3) 0.0455(16) 0.0333(14) -0.0101(14) 0.0200(17) 0.013(2) C1GA 0.0360(12) 0.0205(10) 0.0314(13) -0.0062(10) 0.0004(11) -0.0024(9) C2GA 0.033(3) 0.033(4) 0.041(3) 0.008(2) -0.012(2) 0.010(2) N3GA 0.0319(11) 0.0338(11) 0.0243(11) -0.0008(9) 0.0022(8) 0.0019(9) C4GA 0.057(5) 0.058(5) 0.060(5) 0.016(4) -0.006(4) -0.012(4) C5GA 0.048(2) 0.043(2) 0.0388(18) 0.0000(16) 0.0192(15) 0.0000(16) C1GB 0.0437(14) 0.0222(11) 0.0251(12) -0.0041(9) -0.0023(11) 0.0004(10) N2GB 0.0317(10) 0.0298(10) 0.0233(10) -0.0017(8) 0.0034(8) 0.0030(8) O2 0.0595(19) 0.0391(16) 0.0373(16) -0.0135(15) 0.0210(15) -0.0059(15) C17 0.056(5) 0.047(5) 0.049(3) 0.001(3) 0.006(3) 0.005(4) C18 0.040(3) 0.029(3) 0.028(3) -0.006(2) -0.017(2) 0.015(2) C19 0.057(2) 0.045(2) 0.0269(14) 0.0001(14) 0.0165(15) 0.0057(17) _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 1.4324(12) . ? O1 H1 0.9820(2) . ? C1 C8 1.5361(14) . ? C1 C2 1.5370(15) . ? C1 C14 1.5418(14) . ? C2 C7 1.3954(15) . ? C2 C3 1.3987(15) . ? C3 C4 1.3904(16) . ? C3 H3 0.9500 . ? C4 C5 1.3846(18) . ? C4 H4 0.9500 . ? C5 C6 1.3870(17) . ? C5 H5 0.9500 . ? C6 C7 1.3920(16) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.3936(14) . ? C8 C9 1.3935(15) . ? C9 C10 1.3899(16) . ? C9 H9 0.9500 . ? C10 C11 1.3909(19) . ? C10 H10 0.9500 . ? C11 C12 1.382(2) . ? C11 H11 0.9500 . ? C12 C13 1.3947(17) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C16 1.3934(15) . ? C14 C15 1.3958(14) . ? C15 C16 1.3923(14) 5_656 ? C15 H15 0.9500 . ? C16 C15 1.3923(14) 5_656 ? C16 H16 0.9500 . ? O1G C1GB 1.2487(10) . ? C1GA O2 1.2488(10) . ? C1GA N3GA 1.3485(10) . ? C1GA C2GA 1.4502(10) . ? C2GA H2G1 0.9800 . ? C2GA H2G2 0.9800 . ? C2GA H2G3 0.9800 . ? N3GA C5GA 1.4502(10) . ? N3GA C18 1.4504(10) . ? C4GA C1GB 1.4503(10) . ? C4GA H4G1 0.9800 . ? C4GA H4G2 0.9800 . ? C4GA H4G3 0.9800 . ? C5GA H5G1 0.9800 . ? C5GA H5G2 0.9800 . ? C5GA H5G3 0.9800 . ? C1GB N2GB 1.3484(10) . ? N2GB C17 1.4497(10) . ? N2GB C19 1.4508(10) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 113.8(5) . . ? O1 C1 C8 106.62(8) . . ? O1 C1 C2 109.19(8) . . ? C8 C1 C2 112.40(8) . . ? O1 C1 C14 109.53(8) . . ? C8 C1 C14 105.77(8) . . ? C2 C1 C14 113.10(8) . . ? C7 C2 C3 118.00(10) . . ? C7 C2 C1 121.10(9) . . ? C3 C2 C1 120.74(9) . . ? C4 C3 C2 121.23(11) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 120.03(11) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.50(11) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 120.49(11) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 120.72(10) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C13 C8 C9 118.57(10) . . ? C13 C8 C1 120.81(10) . . ? C9 C8 C1 120.55(9) . . ? C10 C9 C8 120.97(11) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 119.82(12) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 119.86(11) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.16(11) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 120.61(11) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C16 C14 C15 117.72(9) . . ? C16 C14 C1 119.27(9) . . ? C15 C14 C1 122.80(9) . . ? C16 C15 C14 121.20(9) 5_656 . ? C16 C15 H15 119.4 5_656 . ? C14 C15 H15 119.4 . . ? C15 C16 C14 121.07(9) 5_656 . ? C15 C16 H16 119.5 5_656 . ? C14 C16 H16 119.5 . . ? O2 C1GA N3GA 119.7(3) . . ? O2 C1GA C2GA 118.7(4) . . ? N3GA C1GA C2GA 121.4(3) . . ? C1GA C2GA H2G1 109.5 . . ? C1GA C2GA H2G2 109.5 . . ? H2G1 C2GA H2G2 109.5 . . ? C1GA C2GA H2G3 109.5 . . ? H2G1 C2GA H2G3 109.5 . . ? H2G2 C2GA H2G3 109.5 . . ? C1GA N3GA C5GA 124.6(3) . . ? C1GA N3GA C18 122.5(3) . . ? C5GA N3GA C18 112.6(3) . . ? N3GA C5GA H5G1 109.5 . . ? N3GA C5GA H5G2 109.5 . . ? H5G1 C5GA H5G2 109.5 . . ? N3GA C5GA H5G3 109.5 . . ? H5G1 C5GA H5G3 109.5 . . ? H5G2 C5GA H5G3 109.5 . . ? O1G C1GB N2GB 120.9(3) . . ? O1G C1GB C4GA 119.5(4) . . ? N2GB C1GB C4GA 119.7(3) . . ? C1GB N2GB C17 123.3(4) . . ? C1GB N2GB C19 122.7(2) . . ? C17 N2GB C19 113.8(4) . . ? N3GA C18 H18A 109.5 . . ? N3GA C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N3GA C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C7 89.80(12) . . . . ? C8 C1 C2 C7 -28.29(13) . . . . ? C14 C1 C2 C7 -147.98(10) . . . . ? O1 C1 C2 C3 -85.53(11) . . . . ? C8 C1 C2 C3 156.38(10) . . . . ? C14 C1 C2 C3 36.69(13) . . . . ? C7 C2 C3 C4 1.95(17) . . . . ? C1 C2 C3 C4 177.43(10) . . . . ? C2 C3 C4 C5 -1.04(18) . . . . ? C3 C4 C5 C6 -0.40(19) . . . . ? C4 C5 C6 C7 0.89(19) . . . . ? C5 C6 C7 C2 0.06(19) . . . . ? C3 C2 C7 C6 -1.45(17) . . . . ? C1 C2 C7 C6 -176.91(10) . . . . ? O1 C1 C8 C13 10.14(13) . . . . ? C2 C1 C8 C13 129.74(10) . . . . ? C14 C1 C8 C13 -106.39(10) . . . . ? O1 C1 C8 C9 -172.83(9) . . . . ? C2 C1 C8 C9 -53.23(13) . . . . ? C14 C1 C8 C9 70.63(12) . . . . ? C13 C8 C9 C10 -0.71(17) . . . . ? C1 C8 C9 C10 -177.81(11) . . . . ? C8 C9 C10 C11 0.73(19) . . . . ? C9 C10 C11 C12 -0.34(19) . . . . ? C10 C11 C12 C13 -0.05(19) . . . . ? C9 C8 C13 C12 0.32(16) . . . . ? C1 C8 C13 C12 177.40(10) . . . . ? C11 C12 C13 C8 0.06(18) . . . . ? O1 C1 C14 C16 -27.34(12) . . . . ? C8 C1 C14 C16 87.20(11) . . . . ? C2 C1 C14 C16 -149.37(9) . . . . ? O1 C1 C14 C15 157.97(9) . . . . ? C8 C1 C14 C15 -87.48(11) . . . . ? C2 C1 C14 C15 35.95(13) . . . . ? C16 C14 C15 C16 0.44(17) . . . 5_656 ? C1 C14 C15 C16 175.20(9) . . . 5_656 ? C15 C14 C16 C15 -0.44(17) . . . 5_656 ? C1 C14 C16 C15 -175.39(9) . . . 5_656 ? O2 C1GA N3GA C5GA -173.7(4) . . . . ? C2GA C1GA N3GA C5GA 9.6(6) . . . . ? O2 C1GA N3GA C18 -1.0(5) . . . . ? C2GA C1GA N3GA C18 -177.7(6) . . . . ? O1G C1GB N2GB C17 4.1(7) . . . . ? C4GA C1GB N2GB C17 -177.9(8) . . . . ? O1G C1GB N2GB C19 178.4(4) . . . . ? C4GA C1GB N2GB C19 -3.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.340 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.042 # Attachment '- HDMA_b.CIF' data_c:\HDMA_B _database_code_depnum_ccdc_archive 'CCDC 828178' #TrackingRef '- HDMA_b.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1, 4-bis (diphenylhydroxymethyl) benzene dimethylacetamide clathrate polymorph ; _chemical_formula_sum 'C40 H44 N2 O4' _chemical_formula_weight 616.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.263(3) _cell_length_b 13.918(3) _cell_length_c 11.155(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.55(3) _cell_angle_gamma 90.00 _cell_volume 1717.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3290 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25.96 _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(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 'Nonius KappaCCD' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 28554 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.96 _reflns_number_total 3294 _reflns_number_gt 2794 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0520P)^2^+0.3511P] 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 3294 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.002 _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 0.20476(7) 0.07566(6) 0.74347(8) 0.0336(2) Uani 1 1 d . . . C1 C 0.30569(9) 0.03418(7) 0.73061(10) 0.0255(2) Uani 1 1 d . . . H1 H 0.1704(17) 0.0298(14) 0.779(2) 0.078(6) Uiso 1 1 d . . . C2 C 0.34268(9) 0.10773(7) 0.65259(10) 0.0269(2) Uani 1 1 d . . . C3 C 0.30585(11) 0.20286(8) 0.64498(12) 0.0365(3) Uani 1 1 d . . . H3 H 0.2568 0.2220 0.6874 0.044 Uiso 1 1 calc R . . C4 C 0.34018(12) 0.27009(9) 0.57590(14) 0.0455(3) Uani 1 1 d . . . H4 H 0.3132 0.3346 0.5702 0.055 Uiso 1 1 calc R . . C5 C 0.41286(12) 0.24428(9) 0.51552(13) 0.0449(3) Uani 1 1 d . . . H5 H 0.4366 0.2907 0.4689 0.054 Uiso 1 1 calc R . . C6 C 0.45083(12) 0.15045(9) 0.52340(13) 0.0426(3) Uani 1 1 d . . . H6 H 0.5017 0.1322 0.4828 0.051 Uiso 1 1 calc R . . C7 C 0.41519(11) 0.08228(8) 0.59034(12) 0.0345(3) Uani 1 1 d . . . H7 H 0.4407 0.0175 0.5936 0.041 Uiso 1 1 calc R . . C8 C 0.26788(9) -0.06024(7) 0.65208(10) 0.0263(2) Uani 1 1 d . . . C9 C 0.34546(11) -0.13761(8) 0.67622(12) 0.0348(3) Uani 1 1 d . . . H9 H 0.4243 -0.1346 0.7471 0.042 Uiso 1 1 calc R . . C10 C 0.30905(13) -0.21973(9) 0.59775(14) 0.0459(3) Uani 1 1 d . . . H10 H 0.3639 -0.2716 0.6139 0.055 Uiso 1 1 calc R . . C11 C 0.19348(14) -0.22633(10) 0.49635(13) 0.0487(3) Uani 1 1 d . . . H11 H 0.1686 -0.2826 0.4432 0.058 Uiso 1 1 calc R . . C12 C 0.11458(12) -0.15018(10) 0.47314(13) 0.0479(3) Uani 1 1 d . . . H12 H 0.0345 -0.1546 0.4050 0.057 Uiso 1 1 calc R . . C13 C 0.15216(10) -0.06762(9) 0.54898(12) 0.0375(3) Uani 1 1 d . . . H13 H 0.0980 -0.0149 0.5304 0.045 Uiso 1 1 calc R . . C14 C 0.40853(9) 0.01697(7) 0.87005(10) 0.0237(2) Uani 1 1 d . . . C15 C 0.52887(9) 0.03875(8) 0.90419(10) 0.0278(2) Uani 1 1 d . . . H16 H 0.5503 0.0653 0.8388 0.033 Uiso 1 1 calc R . . C16 C 0.38148(9) -0.02272(8) 0.96863(11) 0.0286(2) Uani 1 1 d . . . H15 H 0.3002 -0.0391 0.9485 0.034 Uiso 1 1 calc R . . O1G O 0.0869(13) -0.0261(12) 0.8571(17) 0.053(3) Uani 0.443(8) 1 d P A 2 C1GA C -0.0122(5) 0.0180(5) 0.8374(4) 0.0479(16) Uani 0.443(8) 1 d P A 2 C2GA C -0.0075(10) 0.1226(8) 0.8818(10) 0.052(3) Uani 0.443(8) 1 d P A 2 H2G1 H -0.0036 0.1244 0.9714 0.078 Uiso 0.443(8) 1 calc PR A 2 H2G2 H -0.0802 0.1564 0.8201 0.078 Uiso 0.443(8) 1 calc PR A 2 H2G3 H 0.0642 0.1540 0.8824 0.078 Uiso 0.443(8) 1 calc PR A 2 N3GA N -0.1165(3) -0.0230(4) 0.7784(3) 0.0518(16) Uani 0.443(8) 1 d P A 2 C4GA C -0.1126(8) -0.1262(7) 0.7176(9) 0.082(3) Uani 0.557(8) 1 d P A 1 H4G1 H -0.0621 -0.1827 0.7261 0.123 Uiso 0.557(8) 1 calc PR A 1 H4G2 H -0.1573 -0.1094 0.6234 0.123 Uiso 0.557(8) 1 calc PR A 1 H4G3 H -0.1698 -0.1405 0.7551 0.123 Uiso 0.557(8) 1 calc PR A 1 C5GA C -0.2335(13) 0.0216(11) 0.7503(15) 0.095(4) Uani 0.443(8) 1 d P A 2 H5G1 H -0.2232 0.0687 0.8197 0.142 Uiso 0.443(8) 1 calc PR A 2 H5G2 H -0.2909 -0.0280 0.7486 0.142 Uiso 0.443(8) 1 calc PR A 2 H5G3 H -0.2645 0.0539 0.6639 0.142 Uiso 0.443(8) 1 calc PR A 2 C1GB C -0.0326(2) -0.0419(3) 0.7923(3) 0.0310(11) Uani 0.557(8) 1 d P A 1 N2GB N -0.0870(3) 0.0381(3) 0.8098(2) 0.0396(10) Uani 0.557(8) 1 d P A 1 O2 O 0.0758(12) -0.0452(9) 0.8346(14) 0.0489(16) Uani 0.557(8) 1 d P A 1 C17 C -0.0162(9) 0.1162(7) 0.8833(9) 0.066(3) Uani 0.557(8) 1 d P A 1 H17A H 0.0691 0.0974 0.9251 0.099 Uiso 0.557(8) 1 calc PR A 1 H17B H -0.0418 0.1347 0.9521 0.099 Uiso 0.557(8) 1 calc PR A 1 H17C H -0.0269 0.1707 0.8237 0.099 Uiso 0.557(8) 1 calc PR A 1 C18 C -0.1131(7) -0.1208(7) 0.7235(7) 0.048(3) Uani 0.443(8) 1 d P A 2 H18A H -0.0423 -0.1256 0.7047 0.072 Uiso 0.443(8) 1 calc PR A 2 H18B H -0.1867 -0.1307 0.6413 0.072 Uiso 0.443(8) 1 calc PR A 2 H18C H -0.1081 -0.1699 0.7887 0.072 Uiso 0.443(8) 1 calc PR A 2 C19 C -0.2156(9) 0.0457(7) 0.7680(9) 0.068(2) Uani 0.557(8) 1 d P A 1 H19A H -0.2574 -0.0025 0.6993 0.103 Uiso 0.557(8) 1 calc PR A 1 H19B H -0.2430 0.1100 0.7319 0.103 Uiso 0.557(8) 1 calc PR A 1 H19C H -0.2337 0.0347 0.8443 0.103 Uiso 0.557(8) 1 calc PR A 1 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 0.0285(4) 0.0368(4) 0.0389(4) 0.0064(3) 0.0177(4) 0.0108(3) C1 0.0231(5) 0.0270(5) 0.0272(5) 0.0021(4) 0.0116(4) 0.0035(4) C2 0.0264(5) 0.0255(5) 0.0237(5) 0.0019(4) 0.0059(4) -0.0005(4) C3 0.0390(6) 0.0275(6) 0.0401(6) 0.0006(5) 0.0144(5) 0.0021(5) C4 0.0510(8) 0.0254(6) 0.0512(8) 0.0080(5) 0.0135(6) -0.0006(5) C5 0.0511(8) 0.0383(7) 0.0389(7) 0.0106(5) 0.0135(6) -0.0119(6) C6 0.0516(7) 0.0435(7) 0.0393(7) 0.0033(5) 0.0259(6) -0.0080(6) C7 0.0418(6) 0.0291(6) 0.0371(6) 0.0026(5) 0.0214(5) -0.0004(5) C8 0.0260(5) 0.0282(5) 0.0256(5) 0.0030(4) 0.0120(4) -0.0026(4) C9 0.0345(6) 0.0294(6) 0.0360(6) -0.0003(5) 0.0109(5) -0.0001(5) C10 0.0577(8) 0.0286(6) 0.0522(8) -0.0042(5) 0.0244(7) -0.0017(6) C11 0.0639(9) 0.0396(7) 0.0418(7) -0.0118(6) 0.0220(7) -0.0215(7) C12 0.0423(7) 0.0561(8) 0.0353(7) -0.0047(6) 0.0074(6) -0.0179(6) C13 0.0299(6) 0.0430(7) 0.0336(6) 0.0027(5) 0.0078(5) -0.0025(5) C14 0.0256(5) 0.0204(5) 0.0255(5) -0.0008(4) 0.0113(4) 0.0016(4) C15 0.0280(5) 0.0305(5) 0.0278(5) 0.0036(4) 0.0146(4) 0.0001(4) C16 0.0234(5) 0.0318(5) 0.0313(6) 0.0024(4) 0.0125(4) -0.0016(4) O1G 0.020(3) 0.080(7) 0.058(5) 0.022(4) 0.016(3) 0.005(3) C1GA 0.043(3) 0.067(4) 0.037(2) 0.018(2) 0.0207(18) 0.003(2) C2GA 0.063(5) 0.051(4) 0.044(5) -0.024(4) 0.024(4) -0.026(4) N3GA 0.031(2) 0.080(4) 0.0419(16) 0.0097(18) 0.0141(13) 0.0031(19) C4GA 0.078(6) 0.056(4) 0.089(6) -0.009(3) 0.015(4) -0.037(4) C5GA 0.026(3) 0.160(10) 0.093(5) -0.039(5) 0.020(3) 0.009(4) C1GB 0.024(2) 0.0400(19) 0.0280(12) 0.0079(12) 0.0105(10) -0.0015(11) N2GB 0.0301(16) 0.049(2) 0.0403(12) -0.0011(13) 0.0153(11) 0.0005(14) O2 0.032(3) 0.059(3) 0.053(4) 0.013(2) 0.016(2) -0.0014(18) C17 0.087(6) 0.066(5) 0.053(5) 0.019(4) 0.037(4) 0.024(4) C18 0.048(5) 0.058(5) 0.028(3) 0.011(3) 0.007(3) 0.006(4) C19 0.037(4) 0.099(4) 0.067(3) 0.009(4) 0.020(3) 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 1.4279(12) . ? O1 H1 0.94(2) . ? C1 C2 1.5336(14) . ? C1 C8 1.5359(15) . ? C1 C14 1.5413(15) . ? C2 C7 1.3895(16) . ? C2 C3 1.3896(16) . ? C3 C4 1.3880(18) . ? C3 H3 0.9500 . ? C4 C5 1.377(2) . ? C4 H4 0.9500 . ? C5 C6 1.376(2) . ? C5 H5 0.9500 . ? C6 C7 1.3894(17) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.3842(16) . ? C8 C13 1.3926(16) . ? C9 C10 1.3909(17) . ? C9 H9 0.9500 . ? C10 C11 1.383(2) . ? C10 H10 0.9500 . ? C11 C12 1.382(2) . ? C11 H11 0.9500 . ? C12 C13 1.3829(19) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.3893(15) . ? C14 C16 1.3926(15) . ? C15 C16 1.3878(16) 3_657 ? C15 H16 0.9500 . ? C16 C15 1.3878(16) 3_657 ? C16 H15 0.9500 . ? O1G C1GA 1.294(18) . ? C1GA N3GA 1.292(9) . ? C1GA C2GA 1.531(11) . ? C2GA H2G1 0.9800 . ? C2GA H2G2 0.9800 . ? C2GA H2G3 0.9800 . ? N3GA C5GA 1.468(14) . ? N3GA C18 1.500(11) . ? C4GA C1GB 1.525(8) . ? C4GA H4G1 0.9800 . ? C4GA H4G2 0.9800 . ? C4GA H4G3 0.9800 . ? C5GA H5G1 0.9800 . ? C5GA H5G2 0.9800 . ? C5GA H5G3 0.9800 . ? C1GB O2 1.204(14) . ? C1GB N2GB 1.355(6) . ? N2GB C17 1.412(10) . ? N2GB C19 1.442(10) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.6(12) . . ? O1 C1 C2 105.57(8) . . ? O1 C1 C8 109.98(8) . . ? C2 C1 C8 109.75(8) . . ? O1 C1 C14 109.21(8) . . ? C2 C1 C14 111.28(8) . . ? C8 C1 C14 110.92(8) . . ? C7 C2 C3 118.27(10) . . ? C7 C2 C1 121.54(9) . . ? C3 C2 C1 120.18(10) . . ? C4 C3 C2 120.52(12) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 120.74(12) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 119.28(11) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 120.39(12) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 120.79(11) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C13 118.25(10) . . ? C9 C8 C1 122.79(10) . . ? C13 C8 C1 118.92(10) . . ? C8 C9 C10 120.64(12) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 120.45(12) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.33(12) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 120.05(12) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 121.24(12) . . ? C12 C13 H13 119.4 . . ? C8 C13 H13 119.4 . . ? C15 C14 C16 117.18(10) . . ? C15 C14 C1 123.57(9) . . ? C16 C14 C1 119.25(9) . . ? C16 C15 C14 121.65(10) 3_657 . ? C16 C15 H16 119.2 3_657 . ? C14 C15 H16 119.2 . . ? C15 C16 C14 121.17(10) 3_657 . ? C15 C16 H15 119.4 3_657 . ? C14 C16 H15 119.4 . . ? N3GA C1GA O1G 121.9(9) . . ? N3GA C1GA C2GA 118.4(7) . . ? O1G C1GA C2GA 119.7(8) . . ? C1GA C2GA H2G1 109.5 . . ? C1GA C2GA H2G2 109.5 . . ? H2G1 C2GA H2G2 109.5 . . ? C1GA C2GA H2G3 109.5 . . ? H2G1 C2GA H2G3 109.5 . . ? H2G2 C2GA H2G3 109.5 . . ? C1GA N3GA C5GA 125.7(9) . . ? C1GA N3GA C18 114.4(6) . . ? C5GA N3GA C18 119.6(7) . . ? N3GA C5GA H5G1 109.5 . . ? N3GA C5GA H5G2 109.5 . . ? H5G1 C5GA H5G2 109.5 . . ? N3GA C5GA H5G3 109.5 . . ? H5G1 C5GA H5G3 109.5 . . ? H5G2 C5GA H5G3 109.5 . . ? O2 C1GB N2GB 120.2(7) . . ? O2 C1GB C4GA 121.8(7) . . ? N2GB C1GB C4GA 118.0(5) . . ? C1GB N2GB C17 119.9(5) . . ? C1GB N2GB C19 123.5(5) . . ? C17 N2GB C19 116.4(6) . . ? N3GA C18 H18A 109.5 . . ? N3GA C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N3GA C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C7 -162.28(10) . . . . ? C8 C1 C2 C7 -43.79(13) . . . . ? C14 C1 C2 C7 79.36(12) . . . . ? O1 C1 C2 C3 19.06(13) . . . . ? C8 C1 C2 C3 137.55(10) . . . . ? C14 C1 C2 C3 -99.30(11) . . . . ? C7 C2 C3 C4 0.52(17) . . . . ? C1 C2 C3 C4 179.22(10) . . . . ? C2 C3 C4 C5 -1.07(19) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C4 C5 C6 C7 0.7(2) . . . . ? C3 C2 C7 C6 0.62(17) . . . . ? C1 C2 C7 C6 -178.07(10) . . . . ? C5 C6 C7 C2 -1.23(19) . . . . ? O1 C1 C8 C9 -147.02(10) . . . . ? C2 C1 C8 C9 97.26(12) . . . . ? C14 C1 C8 C9 -26.11(14) . . . . ? O1 C1 C8 C13 35.32(13) . . . . ? C2 C1 C8 C13 -80.40(12) . . . . ? C14 C1 C8 C13 156.23(10) . . . . ? C13 C8 C9 C10 1.12(17) . . . . ? C1 C8 C9 C10 -176.56(11) . . . . ? C8 C9 C10 C11 -1.7(2) . . . . ? C9 C10 C11 C12 0.4(2) . . . . ? C10 C11 C12 C13 1.4(2) . . . . ? C11 C12 C13 C8 -1.9(2) . . . . ? C9 C8 C13 C12 0.68(17) . . . . ? C1 C8 C13 C12 178.45(11) . . . . ? O1 C1 C14 C15 -136.07(10) . . . . ? C2 C1 C14 C15 -19.92(13) . . . . ? C8 C1 C14 C15 102.56(11) . . . . ? O1 C1 C14 C16 44.10(12) . . . . ? C2 C1 C14 C16 160.25(9) . . . . ? C8 C1 C14 C16 -77.26(11) . . . . ? C16 C14 C15 C16 -0.66(17) . . . 3_657 ? C1 C14 C15 C16 179.51(10) . . . 3_657 ? C15 C14 C16 C15 0.66(17) . . . 3_657 ? C1 C14 C16 C15 -179.50(9) . . . 3_657 ? O1G C1GA N3GA C5GA -179.2(13) . . . . ? C2GA C1GA N3GA C5GA -0.5(10) . . . . ? O1G C1GA N3GA C18 -6.0(11) . . . . ? C2GA C1GA N3GA C18 172.6(6) . . . . ? O2 C1GB N2GB C17 -3.0(10) . . . . ? C4GA C1GB N2GB C17 177.3(6) . . . . ? O2 C1GB N2GB C19 -176.7(10) . . . . ? C4GA C1GB N2GB C19 3.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.167 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.032 # Attachment '- HDMF.CIF' data_c:\HDMF _database_code_depnum_ccdc_archive 'CCDC 828179' #TrackingRef '- HDMF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1, 4-bis (diphenylhydroxymethyl) benzene dimethylformamide clathrate ; _chemical_formula_sum 'C38 H40 N2 O4' _chemical_formula_weight 588.72 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 7.6923(11) _cell_length_b 9.1752(13) _cell_length_c 12.7495(18) _cell_angle_alpha 77.960(3) _cell_angle_beta 76.026(3) _cell_angle_gamma 66.760(2) _cell_volume 795.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3939 _cell_measurement_theta_min 0.28 _cell_measurement_theta_max 28.34 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.161 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 314 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(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 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 8988 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 28.34 _reflns_number_total 3939 _reflns_number_gt 3293 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0553P)^2^+0.1822P] 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 3939 _refine_ls_number_parameters 253 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.038 _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 0.36851(11) 0.81732(9) 0.27125(6) 0.02859(19) Uani 1 1 d D . . C1 C 0.25613(14) 0.88329(11) 0.18633(8) 0.0211(2) Uani 1 1 d . . . H1 H 0.3132(17) 0.7475(14) 0.3257(11) 0.064(5) Uiso 1 1 d D . . C2 C 0.20333(14) 0.75152(12) 0.16021(8) 0.0225(2) Uani 1 1 d . . . C3 C 0.01538(15) 0.76430(13) 0.16517(9) 0.0272(2) Uani 1 1 d . . . H3 H -0.0880 0.8601 0.1832 0.033 Uiso 1 1 calc R . . C4 C -0.02283(18) 0.63776(15) 0.14390(11) 0.0353(3) Uani 1 1 d . . . H4 H -0.1518 0.6481 0.1472 0.042 Uiso 1 1 calc R . . C5 C 0.1260(2) 0.49769(15) 0.11813(11) 0.0386(3) Uani 1 1 d . . . H5 H 0.0999 0.4116 0.1036 0.046 Uiso 1 1 calc R . . C6 C 0.31380(19) 0.48329(14) 0.11357(11) 0.0366(3) Uani 1 1 d . . . H6 H 0.4167 0.3869 0.0962 0.044 Uiso 1 1 calc R . . C7 C 0.35212(16) 0.60912(13) 0.13425(10) 0.0300(2) Uani 1 1 d . . . H7 H 0.4814 0.5982 0.1307 0.036 Uiso 1 1 calc R . . C8 C 0.07509(14) 1.02643(12) 0.22104(8) 0.0231(2) Uani 1 1 d . . . C9 C -0.00223(19) 1.03891(17) 0.33043(10) 0.0397(3) Uani 1 1 d . . . H9 H 0.0591 0.9598 0.3845 0.048 Uiso 1 1 calc R . . C10 C -0.1690(2) 1.1665(2) 0.36143(12) 0.0534(4) Uani 1 1 d . . . H10 H -0.2198 1.1744 0.4366 0.064 Uiso 1 1 calc R . . C11 C -0.26120(19) 1.28148(17) 0.28445(13) 0.0446(3) Uani 1 1 d . . . H11 H -0.3752 1.3681 0.3062 0.054 Uiso 1 1 calc R . . C12 C -0.18655(17) 1.26980(14) 0.17508(11) 0.0355(3) Uani 1 1 d . . . H12 H -0.2497 1.3482 0.1213 0.043 Uiso 1 1 calc R . . C13 C -0.01884(15) 1.14308(13) 0.14391(9) 0.0286(2) Uani 1 1 d . . . H13 H 0.0322 1.1362 0.0687 0.034 Uiso 1 1 calc R . . C14 C 0.38526(13) 0.94052(11) 0.08835(8) 0.0202(2) Uani 1 1 d . . . C15 C 0.37846(14) 0.93444(12) -0.01853(8) 0.0234(2) Uani 1 1 d . . . H15 H 0.2950 0.8897 -0.0321 0.028 Uiso 1 1 calc R . . C16 C 0.49170(14) 0.99274(12) -0.10611(8) 0.0231(2) Uani 1 1 d . . . H16 H 0.4850 0.9869 -0.1785 0.028 Uiso 1 1 calc R . . O1G O 0.2464(19) 0.6053(13) 0.4291(6) 0.047(6) Uani 0.176(3) 1 d PD A 2 N1G N 0.2558(13) 0.3554(4) 0.4626(4) 0.0371(7) Uani 0.824(3) 1 d PD A 1 C1GA C 0.2247(4) 0.2317(2) 0.42361(18) 0.0615(6) Uani 0.824(3) 1 d PD A 1 H1G1 H 0.1685 0.2762 0.3574 0.092 Uiso 0.824(3) 1 calc PR A 1 H1G2 H 0.1368 0.1913 0.4798 0.092 Uiso 0.824(3) 1 calc PR A 1 H1G3 H 0.3477 0.1440 0.4074 0.092 Uiso 0.824(3) 1 calc PR A 1 C2GA C 0.2135(2) 0.50294(16) 0.40646(12) 0.0353(4) Uani 0.824(3) 1 d PD A 1 H2GA H 0.1595 0.5236 0.3428 0.042 Uiso 0.824(3) 1 calc PR A 1 C3GA C 0.3334(3) 0.3180(3) 0.56183(16) 0.0614(6) Uani 0.824(3) 1 d PD A 1 H3G1 H 0.2367 0.3020 0.6243 0.092 Uiso 0.824(3) 1 calc PR A 1 H3G2 H 0.3677 0.4066 0.5703 0.092 Uiso 0.824(3) 1 calc PR A 1 H3G3 H 0.4482 0.2202 0.5581 0.092 Uiso 0.824(3) 1 calc PR A 1 C1GB C 0.2926(12) 0.4864(8) 0.4996(6) 0.047(2) Uani 0.176(3) 1 d PD A 2 H1GB H 0.3450 0.4874 0.5596 0.056 Uiso 0.176(3) 1 calc PR A 2 C2GB C 0.1929(15) 0.3580(14) 0.3894(7) 0.062(3) Uani 0.176(3) 1 d PD A 2 H2G1 H 0.1747 0.4613 0.3437 0.092 Uiso 0.176(3) 1 calc PR A 2 H2G2 H 0.0700 0.3418 0.4115 0.092 Uiso 0.176(3) 1 calc PR A 2 H2G3 H 0.2864 0.2721 0.3480 0.092 Uiso 0.176(3) 1 calc PR A 2 C3GB C 0.3151(16) 0.2078(10) 0.5583(9) 0.063(3) Uani 0.176(3) 1 d PD A 2 H3G4 H 0.4094 0.1217 0.5172 0.095 Uiso 0.176(3) 1 calc PR A 2 H3G5 H 0.1999 0.1818 0.5906 0.095 Uiso 0.176(3) 1 calc PR A 2 H3G6 H 0.3707 0.2194 0.6162 0.095 Uiso 0.176(3) 1 calc PR A 2 N1 N 0.264(6) 0.3565(19) 0.485(2) 0.046(3) Uani 0.176(3) 1 d PD A 2 O2 O 0.2413(5) 0.6143(3) 0.43349(15) 0.0515(13) Uani 0.824(3) 1 d PD A 1 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 0.0302(4) 0.0320(4) 0.0261(4) 0.0061(3) -0.0103(3) -0.0157(3) C1 0.0206(4) 0.0217(4) 0.0212(5) -0.0003(4) -0.0035(4) -0.0092(4) C2 0.0254(5) 0.0215(5) 0.0205(5) 0.0003(4) -0.0020(4) -0.0112(4) C3 0.0261(5) 0.0264(5) 0.0299(5) -0.0012(4) -0.0046(4) -0.0117(4) C4 0.0360(6) 0.0382(6) 0.0401(7) -0.0018(5) -0.0088(5) -0.0227(5) C5 0.0524(8) 0.0337(6) 0.0385(7) -0.0064(5) -0.0034(6) -0.0268(6) C6 0.0415(7) 0.0251(5) 0.0400(7) -0.0083(5) 0.0041(5) -0.0131(5) C7 0.0269(5) 0.0257(5) 0.0349(6) -0.0041(4) 0.0016(4) -0.0108(4) C8 0.0224(5) 0.0240(5) 0.0251(5) -0.0056(4) 0.0003(4) -0.0120(4) C9 0.0375(7) 0.0486(7) 0.0267(6) -0.0088(5) -0.0005(5) -0.0101(6) C10 0.0437(8) 0.0689(10) 0.0363(7) -0.0255(7) 0.0076(6) -0.0080(7) C11 0.0294(6) 0.0423(7) 0.0564(8) -0.0235(6) 0.0043(6) -0.0053(5) C12 0.0261(5) 0.0281(5) 0.0481(7) -0.0053(5) -0.0030(5) -0.0073(4) C13 0.0258(5) 0.0265(5) 0.0298(5) -0.0034(4) 0.0002(4) -0.0088(4) C14 0.0174(4) 0.0176(4) 0.0231(5) -0.0015(3) -0.0014(3) -0.0054(3) C15 0.0225(5) 0.0248(5) 0.0258(5) -0.0030(4) -0.0035(4) -0.0123(4) C16 0.0240(5) 0.0245(5) 0.0219(5) -0.0033(4) -0.0033(4) -0.0102(4) O1G 0.072(11) 0.056(10) 0.026(7) 0.006(6) -0.029(7) -0.031(8) N1G 0.0371(11) 0.0378(13) 0.0340(15) 0.0043(12) -0.0030(13) -0.0173(13) C1GA 0.0791(15) 0.0464(11) 0.0653(13) -0.0032(9) -0.0031(11) -0.0369(11) C2GA 0.0384(8) 0.0414(8) 0.0272(7) 0.0030(6) -0.0033(6) -0.0208(7) C3GA 0.0672(13) 0.0693(14) 0.0457(11) 0.0199(10) -0.0231(10) -0.0288(11) C1GB 0.053(5) 0.058(5) 0.035(4) 0.002(3) -0.007(3) -0.030(4) C2GB 0.062(6) 0.079(7) 0.056(6) -0.017(5) -0.004(5) -0.038(5) C3GB 0.070(6) 0.045(5) 0.079(7) 0.017(5) -0.019(5) -0.033(5) N1 0.044(9) 0.044(7) 0.058(13) -0.022(5) 0.013(9) -0.030(8) O2 0.074(2) 0.0429(18) 0.0392(18) 0.0010(13) 0.0049(13) -0.0353(16) _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 1.4323(12) . ? O1 H1 0.9800(2) . ? C1 C2 1.5357(13) . ? C1 C14 1.5367(13) . ? C1 C8 1.5367(14) . ? C2 C3 1.3903(15) . ? C2 C7 1.3942(15) . ? C3 C4 1.3954(15) . ? C3 H3 0.9500 . ? C4 C5 1.3798(19) . ? C4 H4 0.9500 . ? C5 C6 1.3854(19) . ? C5 H5 0.9500 . ? C6 C7 1.3866(16) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.3872(16) . ? C8 C13 1.3887(15) . ? C9 C10 1.3914(19) . ? C9 H9 0.9500 . ? C10 C11 1.376(2) . ? C10 H10 0.9500 . ? C11 C12 1.383(2) . ? C11 H11 0.9500 . ? C12 C13 1.3912(15) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.3896(14) . ? C14 C16 1.3931(13) 2_675 ? C15 C16 1.3930(14) . ? C15 H15 0.9500 . ? C16 C14 1.3931(13) 2_675 ? C16 H16 0.9500 . ? O1G C1GB 1.2501(10) . ? N1G C2GA 1.3455(10) . ? N1G C3GA 1.4481(10) . ? N1G C1GA 1.4489(10) . ? C1GA H1G1 0.9800 . ? C1GA H1G2 0.9800 . ? C1GA H1G3 0.9800 . ? C2GA O2 1.2506(10) . ? C2GA H2GA 0.9500 . ? C3GA H3G1 0.9800 . ? C3GA H3G2 0.9800 . ? C3GA H3G3 0.9800 . ? C1GB N1 1.3496(10) . ? C1GB H1GB 0.9500 . ? C2GB N1 1.4499(10) . ? C2GB H2G1 0.9800 . ? C2GB H2G2 0.9800 . ? C2GB H2G3 0.9800 . ? C3GB N1 1.4504(10) . ? C3GB H3G4 0.9800 . ? C3GB H3G5 0.9800 . ? C3GB H3G6 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.0(9) . . ? O1 C1 C2 108.61(8) . . ? O1 C1 C14 105.67(8) . . ? C2 C1 C14 111.35(8) . . ? O1 C1 C8 110.48(8) . . ? C2 C1 C8 111.11(8) . . ? C14 C1 C8 109.49(8) . . ? C3 C2 C7 118.43(10) . . ? C3 C2 C1 123.59(9) . . ? C7 C2 C1 117.93(9) . . ? C2 C3 C4 120.64(10) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 120.25(11) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.61(11) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 120.23(11) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.84(11) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C9 C8 C13 118.44(10) . . ? C9 C8 C1 120.59(10) . . ? C13 C8 C1 120.93(9) . . ? C8 C9 C10 120.40(12) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.76(13) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.44(12) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C12 C13 119.90(12) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C8 C13 C12 121.05(11) . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C16 118.26(9) . 2_675 ? C15 C14 C1 122.35(8) . . ? C16 C14 C1 119.34(9) 2_675 . ? C14 C15 C16 121.26(9) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C14 120.48(9) . 2_675 ? C15 C16 H16 119.8 . . ? C14 C16 H16 119.8 2_675 . ? C2GA N1G C3GA 120.72(16) . . ? C2GA N1G C1GA 120.02(17) . . ? C3GA N1G C1GA 119.26(17) . . ? O2 C2GA N1G 123.58(17) . . ? O2 C2GA H2GA 118.2 . . ? N1G C2GA H2GA 118.2 . . ? O1G C1GB N1 116.1(7) . . ? O1G C1GB H1GB 122.0 . . ? N1 C1GB H1GB 122.0 . . ? N1 C2GB H2G1 109.5 . . ? N1 C2GB H2G2 109.5 . . ? H2G1 C2GB H2G2 109.5 . . ? N1 C2GB H2G3 109.5 . . ? H2G1 C2GB H2G3 109.5 . . ? H2G2 C2GB H2G3 109.5 . . ? N1 C3GB H3G4 109.5 . . ? N1 C3GB H3G5 109.5 . . ? H3G4 C3GB H3G5 109.5 . . ? N1 C3GB H3G6 109.5 . . ? H3G4 C3GB H3G6 109.5 . . ? H3G5 C3GB H3G6 109.5 . . ? C1GB N1 C2GB 119.8(7) . . ? C1GB N1 C3GB 122.7(8) . . ? C2GB N1 C3GB 117.3(8) . . ? 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 123.24(10) . . . . ? C14 C1 C2 C3 -120.81(10) . . . . ? C8 C1 C2 C3 1.52(14) . . . . ? O1 C1 C2 C7 -54.19(12) . . . . ? C14 C1 C2 C7 61.76(12) . . . . ? C8 C1 C2 C7 -175.91(9) . . . . ? C7 C2 C3 C4 -0.43(16) . . . . ? C1 C2 C3 C4 -177.85(10) . . . . ? C2 C3 C4 C5 0.32(18) . . . . ? C3 C4 C5 C6 0.06(19) . . . . ? C4 C5 C6 C7 -0.32(19) . . . . ? C5 C6 C7 C2 0.21(19) . . . . ? C3 C2 C7 C6 0.17(17) . . . . ? C1 C2 C7 C6 177.73(10) . . . . ? O1 C1 C8 C9 -25.45(13) . . . . ? C2 C1 C8 C9 95.17(12) . . . . ? C14 C1 C8 C9 -141.42(10) . . . . ? O1 C1 C8 C13 156.89(9) . . . . ? C2 C1 C8 C13 -82.49(11) . . . . ? C14 C1 C8 C13 40.92(12) . . . . ? C13 C8 C9 C10 -0.60(19) . . . . ? C1 C8 C9 C10 -178.32(12) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C10 C11 C12 C13 -0.4(2) . . . . ? C9 C8 C13 C12 0.02(16) . . . . ? C1 C8 C13 C12 177.73(10) . . . . ? C11 C12 C13 C8 0.51(18) . . . . ? O1 C1 C14 C15 146.13(9) . . . . ? C2 C1 C14 C15 28.39(13) . . . . ? C8 C1 C14 C15 -94.87(11) . . . . ? O1 C1 C14 C16 -36.63(12) . . . 2_675 ? C2 C1 C14 C16 -154.38(9) . . . 2_675 ? C8 C1 C14 C16 82.36(11) . . . 2_675 ? C16 C14 C15 C16 0.23(16) 2_675 . . . ? C1 C14 C15 C16 177.49(9) . . . . ? C14 C15 C16 C14 -0.24(17) . . . 2_675 ? C3GA N1G C2GA O2 1.7(10) . . . . ? C1GA N1G C2GA O2 -178.0(5) . . . . ? O1G C1GB N1 C2GB 3(4) . . . . ? O1G C1GB N1 C3GB 178(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.306 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.036 # Attachment '- HNMA.CIF' data_c:\HNMA _database_code_depnum_ccdc_archive 'CCDC 828180' #TrackingRef '- HNMA.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1, 4-bis (diphenylhydroxymethyl) benzene N-methylacetamide clathrate ; _chemical_formula_sum 'C38 H40 N2 O4' _chemical_formula_weight 588.72 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5460(12) _cell_length_b 26.221(4) _cell_length_c 9.1335(13) _cell_angle_alpha 90.00 _cell_angle_beta 113.272(2) _cell_angle_gamma 90.00 _cell_volume 1660.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3372 _cell_measurement_theta_min 0.34 _cell_measurement_theta_max 26.42 _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_special_details ; none ; _diffrn_ambient_temperature 173(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 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 6476 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 26.42 _reflns_number_total 3372 _reflns_number_gt 2425 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0652P)^2^+0.7773P] 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 3372 _refine_ls_number_parameters 217 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1304 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.584 _refine_ls_shift/su_max 0.004 _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 0.4651(3) 0.37286(8) 0.1343(2) 0.0289(5) Uani 1 1 d D . . C1 C 0.3174(4) 0.41119(10) 0.0802(3) 0.0227(6) Uani 1 1 d . . . H1 H 0.425(3) 0.3465(6) 0.190(3) 0.058(11) Uiso 1 1 d D . . C2 C 0.1506(4) 0.39391(11) -0.0732(3) 0.0256(6) Uani 1 1 d . . . C3 C 0.0197(4) 0.42915(12) -0.1706(3) 0.0303(7) Uani 1 1 d . . . H3 H 0.0362 0.4643 -0.1433 0.036 Uiso 1 1 calc R . . C4 C -0.1343(5) 0.41400(14) -0.3067(4) 0.0384(8) Uani 1 1 d . . . H4 H -0.2239 0.4386 -0.3705 0.046 Uiso 1 1 calc R . . C5 C -0.1585(5) 0.36357(16) -0.3501(4) 0.0502(10) Uani 1 1 d . . . H5 H -0.2629 0.3532 -0.4446 0.060 Uiso 1 1 calc R . . C6 C -0.0298(6) 0.32821(16) -0.2553(5) 0.0620(12) Uani 1 1 d . . . H6 H -0.0461 0.2932 -0.2843 0.074 Uiso 1 1 calc R . . C7 C 0.1247(5) 0.34319(13) -0.1168(4) 0.0454(9) Uani 1 1 d . . . H7 H 0.2125 0.3183 -0.0523 0.055 Uiso 1 1 calc R . . C8 C 0.2488(4) 0.42223(11) 0.2145(3) 0.0246(6) Uani 1 1 d . . . C9 C 0.0589(5) 0.41766(13) 0.1975(4) 0.0338(7) Uani 1 1 d . . . H9 H -0.0370 0.4076 0.0976 0.041 Uiso 1 1 calc R . . C10 C 0.0064(5) 0.42763(15) 0.3252(4) 0.0435(9) Uani 1 1 d . . . H10 H -0.1244 0.4245 0.3120 0.052 Uiso 1 1 calc R . . C11 C 0.1449(5) 0.44206(14) 0.4705(4) 0.0426(9) Uani 1 1 d . . . H11 H 0.1095 0.4490 0.5575 0.051 Uiso 1 1 calc R . . C12 C 0.3348(5) 0.44640(13) 0.4894(4) 0.0392(8) Uani 1 1 d . . . H12 H 0.4304 0.4562 0.5896 0.047 Uiso 1 1 calc R . . C13 C 0.3868(5) 0.43646(12) 0.3625(3) 0.0318(7) Uani 1 1 d . . . H13 H 0.5181 0.4394 0.3767 0.038 Uiso 1 1 calc R . . C14 C 0.4138(4) 0.45802(10) 0.0424(3) 0.0206(6) Uani 1 1 d . . . C15 C 0.3736(4) 0.50752(11) 0.0730(3) 0.0246(6) Uani 1 1 d . . . H15 H 0.2864 0.5130 0.1232 0.029 Uiso 1 1 calc R . . C16 C 0.4589(3) 0.55009(7) 0.0316(2) 0.0241(6) Uani 1 1 d . . . H16 H 0.4298 0.5837 0.0539 0.029 Uiso 1 1 calc R . . N2 N 0.5483(3) 0.24108(7) 0.5242(2) 0.0401(10) Uani 0.805(7) 1 d PRD A 1 H2 H 0.5342 0.2354 0.6139 0.048 Uiso 0.805(7) 1 d PR A 1 C17 C 0.4402(3) 0.27459(7) 0.4282(2) 0.0396(13) Uani 0.805(7) 1 d PRD A 1 C18 C 0.670(10) 0.216(3) 0.486(7) 0.0564(11) Uani 0.195(7) 1 d PD A 2 H18A H 0.6538 0.1911 0.4023 0.085 Uiso 0.195(7) 1 calc PR A 2 H18B H 0.6546 0.1993 0.5762 0.085 Uiso 0.195(7) 1 calc PR A 2 H18C H 0.7990 0.2313 0.5222 0.085 Uiso 0.195(7) 1 calc PR A 2 C19 C 0.269(6) 0.301(2) 0.483(7) 0.059(2) Uani 0.195(7) 1 d PD A 2 H19A H 0.2660 0.3248 0.4003 0.088 Uiso 0.195(7) 1 calc PR A 2 H19B H 0.2720 0.3192 0.5766 0.088 Uiso 0.195(7) 1 calc PR A 2 H19C H 0.1528 0.2791 0.4414 0.088 Uiso 0.195(7) 1 calc PR A 2 N1 N 0.439(2) 0.2686(5) 0.5263(17) 0.0401(10) Uani 0.19 1 d PD A 2 H1A H 0.4909 0.2560 0.6234 0.048 Uiso 0.195(7) 1 calc PR A 2 O2 O 0.485(8) 0.2830(18) 0.297(4) 0.0489(19) Uani 0.195(7) 1 d PD A 2 O1G O 0.4444(16) 0.2859(4) 0.2966(8) 0.0489(19) Uani 0.805(7) 1 d PD A 1 C20 C 0.519(3) 0.2578(6) 0.4213(18) 0.0396(13) Uani 0.19 1 d PD A 2 C21 C 0.686(2) 0.2116(6) 0.4853(17) 0.0564(11) Uani 0.805(7) 1 d PD A 1 H21A H 0.6174 0.1889 0.3955 0.085 Uiso 0.805(7) 1 calc PR A 1 H21B H 0.7659 0.1912 0.5780 0.085 Uiso 0.805(7) 1 calc PR A 1 H21C H 0.7692 0.2347 0.4562 0.085 Uiso 0.805(7) 1 calc PR A 1 C22 C 0.2984(15) 0.3037(5) 0.4776(14) 0.059(2) Uani 0.805(7) 1 d PD A 1 H22A H 0.3419 0.3390 0.5026 0.088 Uiso 0.805(7) 1 calc PR A 1 H22B H 0.2914 0.2875 0.5719 0.088 Uiso 0.805(7) 1 calc PR A 1 H22C H 0.1706 0.3032 0.3901 0.088 Uiso 0.805(7) 1 calc PR A 1 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 0.0326(11) 0.0259(11) 0.0306(11) 0.0080(9) 0.0149(9) 0.0060(9) C1 0.0243(14) 0.0235(14) 0.0214(13) 0.0020(11) 0.0100(11) 0.0011(11) C2 0.0278(15) 0.0294(15) 0.0226(14) -0.0020(12) 0.0131(12) -0.0047(12) C3 0.0316(16) 0.0357(17) 0.0228(14) -0.0003(13) 0.0100(12) -0.0037(13) C4 0.0306(17) 0.055(2) 0.0266(15) -0.0006(15) 0.0076(13) -0.0064(15) C5 0.041(2) 0.065(3) 0.0358(19) -0.0152(18) 0.0065(16) -0.0176(19) C6 0.061(3) 0.046(2) 0.065(3) -0.025(2) 0.010(2) -0.017(2) C7 0.043(2) 0.0334(18) 0.050(2) -0.0072(16) 0.0079(17) -0.0041(15) C8 0.0309(15) 0.0232(14) 0.0218(14) 0.0047(11) 0.0127(12) -0.0005(12) C9 0.0310(16) 0.0456(19) 0.0266(15) 0.0034(14) 0.0132(13) 0.0008(14) C10 0.0379(19) 0.061(2) 0.0405(19) 0.0074(17) 0.0252(16) 0.0032(17) C11 0.056(2) 0.049(2) 0.0341(18) 0.0006(15) 0.0296(17) 0.0014(17) C12 0.052(2) 0.043(2) 0.0249(16) -0.0060(14) 0.0183(15) -0.0088(16) C13 0.0329(16) 0.0378(17) 0.0250(15) -0.0004(13) 0.0119(13) -0.0076(14) C14 0.0196(13) 0.0255(14) 0.0149(12) 0.0004(11) 0.0047(10) -0.0011(11) C15 0.0263(15) 0.0260(15) 0.0246(14) -0.0003(12) 0.0135(12) 0.0006(12) C16 0.0287(15) 0.0217(14) 0.0241(14) -0.0018(11) 0.0128(12) 0.0002(11) N2 0.063(3) 0.033(2) 0.0300(17) 0.0032(15) 0.0238(17) -0.0041(16) C17 0.066(3) 0.028(2) 0.032(2) -0.0034(18) 0.027(2) -0.011(2) C18 0.072(5) 0.045(4) 0.064(3) 0.001(2) 0.040(3) 0.000(2) C19 0.085(5) 0.047(3) 0.063(3) 0.013(2) 0.049(3) 0.008(3) N1 0.063(3) 0.033(2) 0.0300(17) 0.0032(15) 0.0238(17) -0.0041(16) O2 0.090(6) 0.0322(19) 0.0393(14) 0.0067(11) 0.041(2) 0.004(3) O1G 0.090(6) 0.0322(19) 0.0393(14) 0.0067(11) 0.041(2) 0.004(3) C20 0.066(3) 0.028(2) 0.032(2) -0.0034(18) 0.027(2) -0.011(2) C21 0.072(5) 0.045(4) 0.064(3) 0.001(2) 0.040(3) 0.000(2) C22 0.085(5) 0.047(3) 0.063(3) 0.013(2) 0.049(3) 0.008(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 1.436(3) . ? O1 H1 0.9750(3) . ? C1 C14 1.534(4) . ? C1 C2 1.536(4) . ? C1 C8 1.536(4) . ? C2 C7 1.380(4) . ? C2 C3 1.388(4) . ? C3 C4 1.383(4) . ? C3 H3 0.9500 . ? C4 C5 1.372(5) . ? C4 H4 0.9500 . ? C5 C6 1.374(6) . ? C5 H5 0.9500 . ? C6 C7 1.395(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.385(4) . ? C8 C13 1.392(4) . ? C9 C10 1.397(4) . ? C9 H9 0.9500 . ? C10 C11 1.378(5) . ? C10 H10 0.9500 . ? C11 C12 1.379(5) . ? C11 H11 0.9500 . ? C12 C13 1.387(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.386(4) . ? C14 C16 1.393(3) 3_665 ? C15 C16 1.412(3) . ? C15 H15 0.9500 . ? C16 C14 1.393(3) 3_665 ? C16 H16 0.9500 . ? N2 C17 1.2811 . ? N2 C21 1.4500(16) . ? N2 H2 0.8800 . ? C17 O1G 1.2504(15) . ? C17 C22 1.5199(16) . ? C18 C20 1.5200(16) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 N1 1.4500(16) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N1 C20 1.3502(16) . ? N1 H2 1.2099 . ? N1 H1A 0.8800 . ? O2 C20 1.2501(16) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 108.4(10) . . ? O1 C1 C14 105.4(2) . . ? O1 C1 C2 110.6(2) . . ? C14 C1 C2 108.8(2) . . ? O1 C1 C8 108.5(2) . . ? C14 C1 C8 111.6(2) . . ? C2 C1 C8 111.8(2) . . ? C7 C2 C3 118.2(3) . . ? C7 C2 C1 121.3(3) . . ? C3 C2 C1 120.5(3) . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.2(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C7 120.7(4) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C2 C7 C6 120.4(3) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C13 118.5(3) . . ? C9 C8 C1 123.7(3) . . ? C13 C8 C1 117.9(3) . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.8(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 120.2(3) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C8 120.8(3) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C15 C14 C16 119.2(2) . 3_665 ? C15 C14 C1 122.9(2) . . ? C16 C14 C1 117.8(2) 3_665 . ? C14 C15 C16 121.8(2) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C14 C16 C15 119.0(2) 3_665 . ? C14 C16 H16 120.5 3_665 . ? C15 C16 H16 120.5 . . ? C17 N2 C21 121.5(5) . . ? C17 N2 H2 118.4 . . ? C21 N2 H2 120.0 . . ? O1G C17 N2 124.7(3) . . ? O1G C17 C22 117.0(6) . . ? N2 C17 C22 118.2(5) . . ? C20 C18 H18A 109.5 . . ? C20 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C20 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C20 N1 C19 121(3) . . ? C20 N1 H2 90.1 . . ? C19 N1 H2 146.0 . . ? C20 N1 H1A 119.3 . . ? C19 N1 H1A 119.3 . . ? H2 N1 H1A 31.8 . . ? O2 C20 N1 123(2) . . ? O2 C20 C18 126(3) . . ? N1 C20 C18 110.5(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 O1 C1 C2 C7 18.9(4) . . . . ? C14 C1 C2 C7 134.3(3) . . . . ? C8 C1 C2 C7 -102.1(3) . . . . ? O1 C1 C2 C3 -162.0(2) . . . . ? C14 C1 C2 C3 -46.7(3) . . . . ? C8 C1 C2 C3 77.0(3) . . . . ? C7 C2 C3 C4 0.9(4) . . . . ? C1 C2 C3 C4 -178.2(3) . . . . ? C2 C3 C4 C5 -1.4(5) . . . . ? C3 C4 C5 C6 1.1(6) . . . . ? C4 C5 C6 C7 -0.4(6) . . . . ? C3 C2 C7 C6 -0.2(5) . . . . ? C1 C2 C7 C6 178.9(3) . . . . ? C5 C6 C7 C2 -0.1(6) . . . . ? O1 C1 C8 C9 -123.1(3) . . . . ? C14 C1 C8 C9 121.3(3) . . . . ? C2 C1 C8 C9 -0.8(4) . . . . ? O1 C1 C8 C13 55.4(3) . . . . ? C14 C1 C8 C13 -60.3(3) . . . . ? C2 C1 C8 C13 177.7(3) . . . . ? C13 C8 C9 C10 0.7(5) . . . . ? C1 C8 C9 C10 179.1(3) . . . . ? C8 C9 C10 C11 -0.2(5) . . . . ? C9 C10 C11 C12 -0.2(6) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C8 0.3(5) . . . . ? C9 C8 C13 C12 -0.7(5) . . . . ? C1 C8 C13 C12 -179.3(3) . . . . ? O1 C1 C14 C15 -142.7(2) . . . . ? C2 C1 C14 C15 98.7(3) . . . . ? C8 C1 C14 C15 -25.1(3) . . . . ? O1 C1 C14 C16 39.9(3) . . . 3_665 ? C2 C1 C14 C16 -78.7(3) . . . 3_665 ? C8 C1 C14 C16 157.5(2) . . . 3_665 ? C16 C14 C15 C16 -0.2(4) 3_665 . . . ? C1 C14 C15 C16 -177.5(2) . . . . ? C14 C15 C16 C14 0.2(4) . . . 3_665 ? C21 N2 C17 O1G -1.5(13) . . . . ? C21 N2 C17 C22 179.6(12) . . . . ? C19 N1 C20 O2 18(5) . . . . ? C19 N1 C20 C18 -169(5) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.344 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.046 # Attachment '- HNMF.CIF' data_c:\ctech_~1\web8_nmf\web8nmf _database_code_depnum_ccdc_archive 'CCDC 828181' #TrackingRef '- HNMF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1, 4-bis (diphenylhydroxymethyl) benzene N-methylformamide clathrate ; _chemical_formula_sum 'C34 H31 N O3' _chemical_formula_weight 501.60 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 8.2760(17) _cell_length_b 8.9920(18) _cell_length_c 18.972(4) _cell_angle_alpha 84.68(3) _cell_angle_beta 89.23(3) _cell_angle_gamma 67.92(3) _cell_volume 1302.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6440 _cell_measurement_theta_min 0.06 _cell_measurement_theta_max 28.30 _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(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 'Nonius KappaCCD' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 51799 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6440 _reflns_number_gt 4910 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0519P)^2^+0.5665P] 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 6440 _refine_ls_number_parameters 352 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _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 0.09687(12) 0.31997(11) 0.18727(5) 0.0211(2) Uani 1 1 d D . . C1 C 0.20061(16) 0.29238(15) 0.12462(7) 0.0187(3) Uani 1 1 d . . . H1 H 0.0702(12) 0.4289(7) 0.2003(8) 0.066(7) Uiso 1 1 d D . . C2 C 0.36406(16) 0.33039(15) 0.13529(7) 0.0200(3) Uani 1 1 d . . . C3 C 0.41283(18) 0.35224(17) 0.20240(7) 0.0246(3) Uani 1 1 d . . . H3 H 0.3444 0.3433 0.2420 0.029 Uiso 1 1 calc R . . C4 C 0.56101(19) 0.38715(18) 0.21194(8) 0.0295(3) Uani 1 1 d . . . H4 H 0.5920 0.4030 0.2579 0.035 Uiso 1 1 calc R . . C5 C 0.66349(19) 0.39898(18) 0.15519(9) 0.0302(3) Uani 1 1 d . . . H5 H 0.7642 0.4231 0.1620 0.036 Uiso 1 1 calc R . . C6 C 0.61784(19) 0.37529(18) 0.08830(8) 0.0293(3) Uani 1 1 d . . . H6 H 0.6884 0.3817 0.0491 0.035 Uiso 1 1 calc R . . C7 C 0.46893(18) 0.34219(17) 0.07852(7) 0.0248(3) Uani 1 1 d . . . H7 H 0.4381 0.3273 0.0324 0.030 Uiso 1 1 calc R . . C8 C 0.24366(18) 0.11448(15) 0.11439(7) 0.0207(3) Uani 1 1 d . . . C9 C 0.41223(19) 0.00247(17) 0.10942(7) 0.0263(3) Uani 1 1 d . . . H9 H 0.5086 0.0347 0.1128 0.032 Uiso 1 1 calc R . . C10 C 0.4409(2) -0.15729(18) 0.09951(8) 0.0327(3) Uani 1 1 d . . . H10 H 0.5568 -0.2333 0.0967 0.039 Uiso 1 1 calc R . . C11 C 0.3020(2) -0.20573(18) 0.09382(8) 0.0343(4) Uani 1 1 d . . . H11 H 0.3220 -0.3146 0.0872 0.041 Uiso 1 1 calc R . . C12 C 0.1337(2) -0.09430(18) 0.09785(8) 0.0329(3) Uani 1 1 d . . . H12 H 0.0376 -0.1265 0.0933 0.039 Uiso 1 1 calc R . . C13 C 0.10447(19) 0.06423(17) 0.10852(8) 0.0275(3) Uani 1 1 d . . . H13 H -0.0116 0.1395 0.1119 0.033 Uiso 1 1 calc R . . C14 C 0.09403(16) 0.39927(15) 0.05982(7) 0.0187(3) Uani 1 1 d . . . C15 C -0.01608(18) 0.55858(16) 0.06555(7) 0.0229(3) Uani 1 1 d . . . H15 H -0.0285 0.6008 0.1103 0.028 Uiso 1 1 calc R . . C16 C 0.10815(18) 0.34301(16) -0.00690(7) 0.0227(3) Uani 1 1 d . . . H16 H 0.1824 0.2349 -0.0125 0.027 Uiso 1 1 calc R . . O1A O 0.06300(13) 0.13182(12) 0.31830(5) 0.0252(2) Uani 1 1 d D . . C1A C 0.18270(18) 0.08839(16) 0.37815(7) 0.0220(3) Uani 1 1 d . . . H1A H 0.0972(12) 0.190(2) 0.2799(5) 0.054(6) Uiso 1 1 d D . . C2A C 0.22891(19) 0.23391(17) 0.39099(7) 0.0241(3) Uani 1 1 d . . . C3A C 0.3980(2) 0.23188(19) 0.38856(8) 0.0289(3) Uani 1 1 d . . . H3A H 0.4923 0.1362 0.3791 0.035 Uiso 1 1 calc R . . C4A C 0.4296(2) 0.3698(2) 0.40000(8) 0.0351(4) Uani 1 1 d . . . H4A H 0.5455 0.3669 0.3986 0.042 Uiso 1 1 calc R . . C5A C 0.2942(2) 0.5102(2) 0.41337(8) 0.0375(4) Uani 1 1 d . . . H5A H 0.3164 0.6039 0.4207 0.045 Uiso 1 1 calc R . . C6A C 0.1252(2) 0.51346(19) 0.41599(9) 0.0373(4) Uani 1 1 d . . . H6A H 0.0313 0.6097 0.4253 0.045 Uiso 1 1 calc R . . C7A C 0.0932(2) 0.37645(18) 0.40505(8) 0.0307(3) Uani 1 1 d . . . H7A H -0.0228 0.3797 0.4072 0.037 Uiso 1 1 calc R . . C8A C 0.34458(18) -0.06118(16) 0.36495(7) 0.0227(3) Uani 1 1 d . . . C9A C 0.38258(19) -0.11096(18) 0.29728(7) 0.0275(3) Uani 1 1 d . . . H9A H 0.3070 -0.0520 0.2586 0.033 Uiso 1 1 calc R . . C10A C 0.5296(2) -0.24581(19) 0.28559(8) 0.0327(3) Uani 1 1 d . . . H10A H 0.5522 -0.2791 0.2392 0.039 Uiso 1 1 calc R . . C11A C 0.6429(2) -0.33167(19) 0.34071(8) 0.0322(3) Uani 1 1 d . . . H11A H 0.7438 -0.4231 0.3324 0.039 Uiso 1 1 calc R . . C12A C 0.6079(2) -0.28308(18) 0.40838(8) 0.0305(3) Uani 1 1 d . . . H12A H 0.6855 -0.3412 0.4467 0.037 Uiso 1 1 calc R . . C13A C 0.45991(19) -0.14980(18) 0.42042(8) 0.0272(3) Uani 1 1 d . . . H13A H 0.4367 -0.1184 0.4671 0.033 Uiso 1 1 calc R . . C14A C 0.08469(18) 0.04628(16) 0.44142(7) 0.0216(3) Uani 1 1 d . . . C15A C -0.04528(18) -0.01384(17) 0.43178(7) 0.0248(3) Uani 1 1 d . . . H15A H -0.0781 -0.0237 0.3852 0.030 Uiso 1 1 calc R . . C16A C 0.12761(19) 0.05951(17) 0.51073(7) 0.0251(3) Uani 1 1 d . . . H16A H 0.2152 0.1007 0.5188 0.030 Uiso 1 1 calc R . . C1G C 0.0565(2) -0.29011(19) 0.25171(8) 0.0312(3) Uani 1 1 d . . . H1G H 0.1759 -0.3410 0.2659 0.037 Uiso 1 1 calc R . . N2G N -0.02036(18) -0.13455(16) 0.25792(7) 0.0341(3) Uani 1 1 d . . . H2G H 0.0391 -0.0853 0.2774 0.041 Uiso 1 1 calc R . . C3G C -0.1970(2) -0.0414(2) 0.23428(13) 0.0524(5) Uani 1 1 d . . . H4GA H -0.2302 -0.0952 0.1976 0.079 Uiso 1 1 calc R . . H3GA H -0.2060 0.0662 0.2147 0.079 Uiso 1 1 calc R . . H5GA H -0.2751 -0.0319 0.2743 0.079 Uiso 1 1 calc R . . O4G O -0.01456(15) -0.37444(12) 0.22887(6) 0.0339(3) Uani 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 0.0229(5) 0.0212(5) 0.0191(5) -0.0006(4) 0.0028(4) -0.0087(4) C1 0.0191(6) 0.0193(6) 0.0171(6) 0.0005(5) -0.0002(5) -0.0068(5) C2 0.0191(6) 0.0160(6) 0.0233(6) 0.0010(5) -0.0018(5) -0.0053(5) C3 0.0230(7) 0.0267(7) 0.0236(7) -0.0015(5) -0.0006(5) -0.0091(6) C4 0.0269(7) 0.0322(8) 0.0301(8) -0.0047(6) -0.0064(6) -0.0113(6) C5 0.0214(7) 0.0267(7) 0.0432(9) -0.0002(6) -0.0038(6) -0.0104(6) C6 0.0239(7) 0.0300(7) 0.0331(8) 0.0023(6) 0.0031(6) -0.0105(6) C7 0.0245(7) 0.0272(7) 0.0223(7) -0.0004(5) 0.0010(5) -0.0095(6) C8 0.0260(7) 0.0189(6) 0.0154(6) 0.0015(5) -0.0009(5) -0.0070(5) C9 0.0264(7) 0.0245(7) 0.0256(7) 0.0000(5) -0.0004(6) -0.0074(6) C10 0.0362(8) 0.0217(7) 0.0324(8) -0.0032(6) 0.0046(6) -0.0022(6) C11 0.0505(10) 0.0207(7) 0.0313(8) -0.0041(6) 0.0052(7) -0.0127(7) C12 0.0413(9) 0.0275(8) 0.0355(8) -0.0022(6) 0.0015(7) -0.0196(7) C13 0.0275(7) 0.0234(7) 0.0317(8) -0.0005(6) 0.0005(6) -0.0103(6) C14 0.0186(6) 0.0188(6) 0.0196(6) 0.0009(5) -0.0013(5) -0.0086(5) C15 0.0279(7) 0.0205(6) 0.0196(6) -0.0023(5) -0.0012(5) -0.0080(5) C16 0.0255(7) 0.0177(6) 0.0221(7) -0.0009(5) -0.0014(5) -0.0050(5) O1A 0.0272(5) 0.0300(5) 0.0198(5) 0.0040(4) -0.0031(4) -0.0137(4) C1A 0.0242(7) 0.0256(7) 0.0179(6) 0.0016(5) -0.0010(5) -0.0120(5) C2A 0.0314(7) 0.0269(7) 0.0170(6) 0.0033(5) -0.0004(5) -0.0155(6) C3A 0.0326(8) 0.0343(8) 0.0241(7) 0.0000(6) 0.0010(6) -0.0181(6) C4A 0.0422(9) 0.0454(9) 0.0293(8) 0.0011(7) -0.0010(7) -0.0306(8) C5A 0.0579(11) 0.0332(8) 0.0311(8) 0.0021(6) -0.0047(7) -0.0291(8) C6A 0.0494(10) 0.0260(8) 0.0359(9) 0.0015(6) -0.0016(7) -0.0144(7) C7A 0.0336(8) 0.0271(7) 0.0320(8) 0.0030(6) -0.0015(6) -0.0134(6) C8A 0.0250(7) 0.0249(7) 0.0216(7) 0.0006(5) 0.0010(5) -0.0137(6) C9A 0.0294(7) 0.0317(7) 0.0217(7) 0.0004(6) -0.0007(6) -0.0124(6) C10A 0.0346(8) 0.0366(8) 0.0258(7) -0.0057(6) 0.0043(6) -0.0119(7) C11A 0.0292(8) 0.0299(8) 0.0349(8) -0.0017(6) 0.0034(6) -0.0086(6) C12A 0.0291(7) 0.0309(8) 0.0293(8) 0.0041(6) -0.0047(6) -0.0102(6) C13A 0.0302(7) 0.0313(7) 0.0212(7) -0.0006(6) -0.0009(6) -0.0134(6) C14A 0.0241(7) 0.0205(6) 0.0209(6) 0.0000(5) 0.0014(5) -0.0096(5) C15A 0.0288(7) 0.0292(7) 0.0197(6) -0.0017(5) 0.0000(5) -0.0149(6) C16A 0.0281(7) 0.0295(7) 0.0231(7) -0.0018(5) 0.0006(5) -0.0171(6) C1G 0.0355(8) 0.0359(8) 0.0201(7) -0.0023(6) 0.0001(6) -0.0114(7) N2G 0.0408(8) 0.0339(7) 0.0338(7) -0.0095(6) 0.0047(6) -0.0199(6) C3G 0.0405(10) 0.0323(9) 0.0804(15) -0.0050(9) 0.0087(10) -0.0095(8) O4G 0.0440(6) 0.0293(6) 0.0292(6) -0.0086(4) 0.0039(5) -0.0134(5) _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 1.4419(16) . ? O1 H1 0.9750(3) . ? C1 C8 1.5333(18) . ? C1 C2 1.5348(18) . ? C1 C14 1.5447(18) . ? C2 C3 1.3936(19) . ? C2 C7 1.3955(19) . ? C3 C4 1.393(2) . ? C3 H3 0.9500 . ? C4 C5 1.383(2) . ? C4 H4 0.9500 . ? C5 C6 1.386(2) . ? C5 H5 0.9500 . ? C6 C7 1.391(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.388(2) . ? C8 C13 1.396(2) . ? C9 C10 1.396(2) . ? C9 H9 0.9500 . ? C10 C11 1.383(2) . ? C10 H10 0.9500 . ? C11 C12 1.383(2) . ? C11 H11 0.9500 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.3927(19) . ? C14 C16 1.3935(19) . ? C15 C16 1.3911(19) 2_565 ? C15 H15 0.9500 . ? C16 C15 1.3911(19) 2_565 ? C16 H16 0.9500 . ? O1A C1A 1.4424(17) . ? O1A H1A 0.9600(3) . ? C1A C2A 1.5348(19) . ? C1A C14A 1.5371(19) . ? C1A C8A 1.538(2) . ? C2A C3A 1.393(2) . ? C2A C7A 1.396(2) . ? C3A C4A 1.396(2) . ? C3A H3A 0.9500 . ? C4A C5A 1.379(3) . ? C4A H4A 0.9500 . ? C5A C6A 1.388(3) . ? C5A H5A 0.9500 . ? C6A C7A 1.387(2) . ? C6A H6A 0.9500 . ? C7A H7A 0.9500 . ? C8A C9A 1.392(2) . ? C8A C13A 1.398(2) . ? C9A C10A 1.391(2) . ? C9A H9A 0.9500 . ? C10A C11A 1.379(2) . ? C10A H10A 0.9500 . ? C11A C12A 1.386(2) . ? C11A H11A 0.9500 . ? C12A C13A 1.389(2) . ? C12A H12A 0.9500 . ? C13A H13A 0.9500 . ? C14A C16A 1.3939(19) . ? C14A C15A 1.3940(19) . ? C15A C16A 1.389(2) 2_556 ? C15A H15A 0.9500 . ? C16A C15A 1.3893(19) 2_556 ? C16A H16A 0.9500 . ? C1G O4G 1.2294(19) . ? C1G N2G 1.317(2) . ? C1G H1G 0.9500 . ? N2G C3G 1.438(2) . ? N2G H2G 0.8800 . ? C3G H4GA 0.9800 . ? C3G H3GA 0.9800 . ? C3G H5GA 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 110.7(6) . . ? O1 C1 C8 104.59(10) . . ? O1 C1 C2 110.05(10) . . ? C8 C1 C2 112.76(11) . . ? O1 C1 C14 110.51(10) . . ? C8 C1 C14 109.56(10) . . ? C2 C1 C14 109.31(10) . . ? C3 C2 C7 118.17(12) . . ? C3 C2 C1 120.66(12) . . ? C7 C2 C1 121.17(12) . . ? C4 C3 C2 120.57(13) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 120.66(14) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.36(13) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C7 120.07(14) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C2 121.16(13) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? C9 C8 C13 118.64(13) . . ? C9 C8 C1 123.70(12) . . ? C13 C8 C1 117.65(12) . . ? C8 C9 C10 120.35(14) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.50(14) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 119.43(14) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C12 C13 120.30(15) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 120.76(14) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C15 C14 C16 117.31(12) . . ? C15 C14 C1 120.84(12) . . ? C16 C14 C1 121.81(11) . . ? C16 C15 C14 121.11(13) 2_565 . ? C16 C15 H15 119.4 2_565 . ? C14 C15 H15 119.4 . . ? C15 C16 C14 121.58(12) 2_565 . ? C15 C16 H16 119.2 2_565 . ? C14 C16 H16 119.2 . . ? C1A O1A H1A 112.1(3) . . ? O1A C1A C2A 108.80(11) . . ? O1A C1A C14A 105.86(10) . . ? C2A C1A C14A 110.50(11) . . ? O1A C1A C8A 109.90(11) . . ? C2A C1A C8A 112.43(11) . . ? C14A C1A C8A 109.15(11) . . ? C3A C2A C7A 118.43(13) . . ? C3A C2A C1A 123.63(13) . . ? C7A C2A C1A 117.94(13) . . ? C2A C3A C4A 120.32(15) . . ? C2A C3A H3A 119.8 . . ? C4A C3A H3A 119.8 . . ? C5A C4A C3A 120.67(15) . . ? C5A C4A H4A 119.7 . . ? C3A C4A H4A 119.7 . . ? C4A C5A C6A 119.47(15) . . ? C4A C5A H5A 120.3 . . ? C6A C5A H5A 120.3 . . ? C7A C6A C5A 120.10(16) . . ? C7A C6A H6A 120.0 . . ? C5A C6A H6A 120.0 . . ? C6A C7A C2A 121.01(15) . . ? C6A C7A H7A 119.5 . . ? C2A C7A H7A 119.5 . . ? C9A C8A C13A 117.89(13) . . ? C9A C8A C1A 121.13(13) . . ? C13A C8A C1A 120.97(12) . . ? C10A C9A C8A 120.89(14) . . ? C10A C9A H9A 119.6 . . ? C8A C9A H9A 119.6 . . ? C11A C10A C9A 120.65(14) . . ? C11A C10A H10A 119.7 . . ? C9A C10A H10A 119.7 . . ? C10A C11A C12A 119.25(14) . . ? C10A C11A H11A 120.4 . . ? C12A C11A H11A 120.4 . . ? C11A C12A C13A 120.26(14) . . ? C11A C12A H12A 119.9 . . ? C13A C12A H12A 119.9 . . ? C12A C13A C8A 121.05(14) . . ? C12A C13A H13A 119.5 . . ? C8A C13A H13A 119.5 . . ? C16A C14A C15A 117.42(12) . . ? C16A C14A C1A 121.42(12) . . ? C15A C14A C1A 121.09(12) . . ? C16A C15A C14A 121.02(13) 2_556 . ? C16A C15A H15A 119.5 2_556 . ? C14A C15A H15A 119.5 . . ? C15A C16A C14A 121.56(13) 2_556 . ? C15A C16A H16A 119.2 2_556 . ? C14A C16A H16A 119.2 . . ? O4G C1G N2G 124.93(15) . . ? O4G C1G H1G 117.5 . . ? N2G C1G H1G 117.5 . . ? C1G N2G C3G 123.03(15) . . ? C1G N2G H2G 118.5 . . ? C3G N2G H2G 118.5 . . ? N2G C3G H4GA 109.5 . . ? N2G C3G H3GA 109.5 . . ? H4GA C3G H3GA 109.5 . . ? N2G C3G H5GA 109.5 . . ? H4GA C3G H5GA 109.5 . . ? H3GA C3G H5GA 109.5 . . ? 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 12.71(16) . . . . ? C8 C1 C2 C3 -103.64(14) . . . . ? C14 C1 C2 C3 134.25(13) . . . . ? O1 C1 C2 C7 -168.04(11) . . . . ? C8 C1 C2 C7 75.60(15) . . . . ? C14 C1 C2 C7 -46.51(16) . . . . ? C7 C2 C3 C4 0.9(2) . . . . ? C1 C2 C3 C4 -179.84(12) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C3 C4 C5 C6 -0.2(2) . . . . ? C4 C5 C6 C7 0.9(2) . . . . ? C5 C6 C7 C2 -0.7(2) . . . . ? C3 C2 C7 C6 -0.2(2) . . . . ? C1 C2 C7 C6 -179.45(12) . . . . ? O1 C1 C8 C9 -124.58(13) . . . . ? C2 C1 C8 C9 -5.02(17) . . . . ? C14 C1 C8 C9 116.95(14) . . . . ? O1 C1 C8 C13 56.63(14) . . . . ? C2 C1 C8 C13 176.19(11) . . . . ? C14 C1 C8 C13 -61.84(15) . . . . ? C13 C8 C9 C10 -0.7(2) . . . . ? C1 C8 C9 C10 -179.45(13) . . . . ? C8 C9 C10 C11 0.6(2) . . . . ? C9 C10 C11 C12 0.2(2) . . . . ? C10 C11 C12 C13 -0.9(2) . . . . ? C11 C12 C13 C8 0.9(2) . . . . ? C9 C8 C13 C12 -0.1(2) . . . . ? C1 C8 C13 C12 178.78(13) . . . . ? O1 C1 C14 C15 40.64(16) . . . . ? C8 C1 C14 C15 155.37(12) . . . . ? C2 C1 C14 C15 -80.62(15) . . . . ? O1 C1 C14 C16 -141.62(12) . . . . ? C8 C1 C14 C16 -26.89(16) . . . . ? C2 C1 C14 C16 97.12(14) . . . . ? C16 C14 C15 C16 0.1(2) . . . 2_565 ? C1 C14 C15 C16 177.93(12) . . . 2_565 ? C15 C14 C16 C15 -0.1(2) . . . 2_565 ? C1 C14 C16 C15 -177.91(12) . . . 2_565 ? O1A C1A C2A C3A -119.95(14) . . . . ? C14A C1A C2A C3A 124.24(14) . . . . ? C8A C1A C2A C3A 2.02(18) . . . . ? O1A C1A C2A C7A 59.27(16) . . . . ? C14A C1A C2A C7A -56.54(16) . . . . ? C8A C1A C2A C7A -178.75(12) . . . . ? C7A C2A C3A C4A 0.0(2) . . . . ? C1A C2A C3A C4A 179.24(13) . . . . ? C2A C3A C4A C5A -0.5(2) . . . . ? C3A C4A C5A C6A 0.5(2) . . . . ? C4A C5A C6A C7A -0.1(2) . . . . ? C5A C6A C7A C2A -0.3(2) . . . . ? C3A C2A C7A C6A 0.4(2) . . . . ? C1A C2A C7A C6A -178.91(13) . . . . ? O1A C1A C8A C9A 16.33(17) . . . . ? C2A C1A C8A C9A -105.01(15) . . . . ? C14A C1A C8A C9A 132.01(13) . . . . ? O1A C1A C8A C13A -164.80(12) . . . . ? C2A C1A C8A C13A 73.86(16) . . . . ? C14A C1A C8A C13A -49.12(16) . . . . ? C13A C8A C9A C10A 0.8(2) . . . . ? C1A C8A C9A C10A 179.67(13) . . . . ? C8A C9A C10A C11A -1.2(2) . . . . ? C9A C10A C11A C12A 0.6(2) . . . . ? C10A C11A C12A C13A 0.3(2) . . . . ? C11A C12A C13A C8A -0.7(2) . . . . ? C9A C8A C13A C12A 0.1(2) . . . . ? C1A C8A C13A C12A -178.76(13) . . . . ? O1A C1A C14A C16A -154.71(12) . . . . ? C2A C1A C14A C16A -37.08(17) . . . . ? C8A C1A C14A C16A 87.05(15) . . . . ? O1A C1A C14A C15A 28.31(17) . . . . ? C2A C1A C14A C15A 145.95(13) . . . . ? C8A C1A C14A C15A -89.93(15) . . . . ? C16A C14A C15A C16A -0.4(2) . . . 2_556 ? C1A C14A C15A C16A 176.71(13) . . . 2_556 ? C15A C14A C16A C15A 0.4(2) . . . 2_556 ? C1A C14A C16A C15A -176.70(13) . . . 2_556 ? O4G C1G N2G C3G -3.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.256 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.051 # Attachment '- H_dihydrate.CIF' data_c:\H_2H2O _database_code_depnum_ccdc_archive 'CCDC 828182' #TrackingRef '- H_dihydrate.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1, 4-bis (diphenylhydroxymethyl) benzene dihydrate ; _chemical_formula_sum 'C32 H30 O4' _chemical_formula_weight 478.56 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 10.3078(6) _cell_length_b 10.8225(6) _cell_length_c 11.6724(6) _cell_angle_alpha 77.501(2) _cell_angle_beta 77.6420(10) _cell_angle_gamma 88.4400(10) _cell_volume 1241.56(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5087 _cell_measurement_theta_min 0.37 _cell_measurement_theta_max 26.51 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.083 _exptl_special_details ; none ; _diffrn_ambient_temperature 173(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 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 9799 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.51 _reflns_number_total 5087 _reflns_number_gt 4477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0445P)^2^+0.4775P] 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 5087 _refine_ls_number_parameters 349 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.024 _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 0.35796(8) 0.07038(7) 0.41562(7) 0.02320(19) Uani 1 1 d D . . C1 C 0.26381(11) 0.06754(11) 0.34130(10) 0.0201(2) Uani 1 1 d . . . H1 H 0.3718(13) -0.0142(4) 0.4617(11) 0.054(5) Uiso 1 1 d D . . C2 C 0.30618(12) -0.03072(11) 0.26390(10) 0.0216(2) Uani 1 1 d . . . C3 C 0.21432(13) -0.10304(12) 0.23382(11) 0.0282(3) Uani 1 1 d . . . H3 H 0.1240 -0.0938 0.2625 0.034 Uiso 1 1 calc R . . C4 C 0.25647(15) -0.18915(13) 0.16111(13) 0.0354(3) Uani 1 1 d . . . H4 H 0.1942 -0.2375 0.1421 0.042 Uiso 1 1 calc R . . C5 C 0.39047(15) -0.20302(13) 0.11711(13) 0.0355(3) Uani 1 1 d . . . H5 H 0.4185 -0.2606 0.0686 0.043 Uiso 1 1 calc R . . C6 C 0.48270(14) -0.13059(13) 0.14573(12) 0.0337(3) Uani 1 1 d . . . H6 H 0.5729 -0.1391 0.1160 0.040 Uiso 1 1 calc R . . C7 C 0.44071(13) -0.04532(12) 0.21870(12) 0.0284(3) Uani 1 1 d . . . H7 H 0.5033 0.0027 0.2377 0.034 Uiso 1 1 calc R . . C8 C 0.27047(11) 0.20182(11) 0.26284(10) 0.0208(2) Uani 1 1 d . . . C9 C 0.26612(13) 0.30480(12) 0.31713(11) 0.0271(3) Uani 1 1 d . . . H9 H 0.2584 0.2908 0.3998 0.033 Uiso 1 1 calc R . . C10 C 0.27312(14) 0.42777(12) 0.25006(12) 0.0322(3) Uani 1 1 d . . . H10 H 0.2705 0.4955 0.2877 0.039 Uiso 1 1 calc R . . C11 C 0.28401(15) 0.44980(12) 0.12697(13) 0.0344(3) Uani 1 1 d . . . H11 H 0.2889 0.5322 0.0816 0.041 Uiso 1 1 calc R . . C12 C 0.28757(16) 0.34864(13) 0.07217(12) 0.0375(3) Uani 1 1 d . . . H12 H 0.2947 0.3631 -0.0105 0.045 Uiso 1 1 calc R . . C13 C 0.28056(14) 0.22509(12) 0.13952(11) 0.0300(3) Uani 1 1 d . . . H13 H 0.2827 0.1576 0.1016 0.036 Uiso 1 1 calc R . . C14 C 0.12576(11) 0.03433(11) 0.42308(10) 0.0200(2) Uani 1 1 d . . . C15 C 0.11045(12) -0.06731(12) 0.52142(11) 0.0267(3) Uani 1 1 d . . . H15 H 0.1844 -0.1138 0.5369 0.032 Uiso 1 1 calc R . . C16 C 0.01270(12) 0.10080(12) 0.40314(11) 0.0257(3) Uani 1 1 d . . . H16 H 0.0196 0.1690 0.3380 0.031 Uiso 1 1 calc R . . O1A O -0.32708(8) 0.56943(8) 0.44284(7) 0.02368(19) Uani 1 1 d D . . C1A C -0.20424(11) 0.56855(11) 0.35569(10) 0.0202(2) Uani 1 1 d . . . H1A H -0.3501(6) 0.4867(8) 0.4959(14) 0.063(6) Uiso 1 1 d D . . C2A C -0.21575(12) 0.47164(11) 0.27963(10) 0.0228(2) Uani 1 1 d . . . C3A C -0.10422(14) 0.41253(13) 0.22718(12) 0.0325(3) Uani 1 1 d . . . H3A H -0.0213 0.4295 0.2403 0.039 Uiso 1 1 calc R . . C4A C -0.11588(17) 0.32846(14) 0.15536(13) 0.0425(4) Uani 1 1 d . . . H4A H -0.0406 0.2899 0.1202 0.051 Uiso 1 1 calc R . . C5A C -0.23868(18) 0.30154(13) 0.13568(13) 0.0409(4) Uani 1 1 d . . . H5A H -0.2462 0.2441 0.0885 0.049 Uiso 1 1 calc R . . C6A C -0.34972(16) 0.36019(13) 0.18622(12) 0.0358(3) Uani 1 1 d . . . H6A H -0.4324 0.3429 0.1727 0.043 Uiso 1 1 calc R . . C7A C -0.33848(13) 0.44513(12) 0.25735(11) 0.0280(3) Uani 1 1 d . . . H7A H -0.4139 0.4849 0.2906 0.034 Uiso 1 1 calc R . . C8A C -0.18660(11) 0.70303(11) 0.27710(10) 0.0211(2) Uani 1 1 d . . . C9A C -0.23408(13) 0.80652(12) 0.32579(11) 0.0264(3) Uani 1 1 d . . . H9A H -0.2767 0.7935 0.4063 0.032 Uiso 1 1 calc R . . C10A C -0.21866(13) 0.92873(12) 0.25599(12) 0.0300(3) Uani 1 1 d . . . H10A H -0.2499 0.9969 0.2900 0.036 Uiso 1 1 calc R . . C11A C -0.15685(14) 0.94913(12) 0.13594(13) 0.0331(3) Uani 1 1 d . . . H11A H -0.1477 1.0307 0.0886 0.040 Uiso 1 1 calc R . . C12A C -0.10871(15) 0.84742(13) 0.08672(13) 0.0348(3) Uani 1 1 d . . . H12A H -0.0667 0.8609 0.0060 0.042 Uiso 1 1 calc R . . C13A C -0.12243(13) 0.72544(12) 0.15659(11) 0.0280(3) Uani 1 1 d . . . H13A H -0.0885 0.6580 0.1226 0.034 Uiso 1 1 calc R . . C14A C -0.09402(11) 0.53432(11) 0.42705(10) 0.0204(2) Uani 1 1 d . . . C15A C -0.09262(12) 0.41224(11) 0.49689(11) 0.0240(3) Uani 1 1 d . . . H15A H -0.1548 0.3522 0.4954 0.029 Uiso 1 1 calc R . . C16A C 0.00019(12) 0.62144(11) 0.43140(11) 0.0232(2) Uani 1 1 d . . . H16A H 0.0015 0.7034 0.3857 0.028 Uiso 1 1 calc R . . O1G O -0.56944(9) 0.65775(9) 0.41290(10) 0.0355(2) Uani 1 1 d D . . O2G O 0.59096(10) 0.15272(8) 0.44808(10) 0.0377(2) Uani 1 1 d D . . H1GB H -0.575(2) 0.703(2) 0.343(2) 0.074(7) Uiso 1 1 d . . . H2GA H 0.5087(9) 0.1390(9) 0.4229(10) 0.056(5) Uiso 1 1 d D . . H1GA H -0.4770(5) 0.6331(18) 0.4074(6) 0.081(7) Uiso 1 1 d D . . H2GB H 0.5764(17) 0.2216(11) 0.4889(13) 0.080(7) Uiso 1 1 d 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 0.0214(4) 0.0252(4) 0.0246(4) -0.0047(3) -0.0090(3) -0.0004(3) C1 0.0190(5) 0.0224(5) 0.0199(5) -0.0051(4) -0.0055(4) 0.0004(4) C2 0.0231(6) 0.0208(5) 0.0196(5) -0.0028(4) -0.0032(4) 0.0012(4) C3 0.0243(6) 0.0313(6) 0.0291(7) -0.0105(5) -0.0018(5) -0.0019(5) C4 0.0368(8) 0.0363(7) 0.0363(7) -0.0173(6) -0.0045(6) -0.0060(6) C5 0.0413(8) 0.0351(7) 0.0320(7) -0.0175(6) -0.0019(6) 0.0046(6) C6 0.0277(7) 0.0404(7) 0.0326(7) -0.0134(6) -0.0004(5) 0.0060(6) C7 0.0237(6) 0.0320(6) 0.0302(7) -0.0102(5) -0.0035(5) 0.0003(5) C8 0.0165(5) 0.0235(6) 0.0212(6) -0.0035(4) -0.0025(4) -0.0008(4) C9 0.0323(7) 0.0268(6) 0.0222(6) -0.0057(5) -0.0053(5) 0.0022(5) C10 0.0406(8) 0.0241(6) 0.0329(7) -0.0075(5) -0.0088(6) 0.0020(5) C11 0.0428(8) 0.0243(6) 0.0330(7) 0.0032(5) -0.0105(6) -0.0008(5) C12 0.0542(9) 0.0348(7) 0.0220(6) -0.0005(5) -0.0103(6) -0.0016(6) C13 0.0402(8) 0.0278(6) 0.0228(6) -0.0063(5) -0.0074(5) -0.0009(5) C14 0.0207(6) 0.0211(5) 0.0192(5) -0.0070(4) -0.0038(4) 0.0008(4) C15 0.0199(6) 0.0262(6) 0.0308(7) 0.0004(5) -0.0056(5) 0.0045(5) C16 0.0235(6) 0.0255(6) 0.0246(6) 0.0023(5) -0.0052(5) 0.0014(5) O1A 0.0200(4) 0.0262(4) 0.0240(4) -0.0060(3) -0.0025(3) 0.0026(3) C1A 0.0184(5) 0.0226(5) 0.0203(6) -0.0062(4) -0.0042(4) 0.0030(4) C2A 0.0291(6) 0.0195(5) 0.0205(6) -0.0025(4) -0.0087(5) 0.0029(5) C3A 0.0350(7) 0.0363(7) 0.0312(7) -0.0135(6) -0.0132(6) 0.0127(6) C4A 0.0599(10) 0.0405(8) 0.0347(8) -0.0185(6) -0.0192(7) 0.0258(7) C5A 0.0727(11) 0.0280(7) 0.0311(7) -0.0120(6) -0.0264(7) 0.0082(7) C6A 0.0490(9) 0.0318(7) 0.0309(7) -0.0054(6) -0.0186(6) -0.0058(6) C7A 0.0313(7) 0.0284(6) 0.0258(6) -0.0057(5) -0.0093(5) -0.0002(5) C8A 0.0194(6) 0.0229(6) 0.0228(6) -0.0046(5) -0.0087(4) 0.0027(4) C9A 0.0296(7) 0.0268(6) 0.0241(6) -0.0068(5) -0.0076(5) 0.0047(5) C10A 0.0321(7) 0.0236(6) 0.0369(7) -0.0087(5) -0.0114(6) 0.0050(5) C11A 0.0346(7) 0.0238(6) 0.0375(7) 0.0016(5) -0.0078(6) -0.0030(5) C12A 0.0376(8) 0.0337(7) 0.0281(7) -0.0026(6) 0.0008(6) -0.0043(6) C13A 0.0288(7) 0.0270(6) 0.0272(6) -0.0077(5) -0.0020(5) 0.0011(5) C14A 0.0196(6) 0.0237(6) 0.0188(5) -0.0072(4) -0.0043(4) 0.0040(4) C15A 0.0225(6) 0.0227(6) 0.0284(6) -0.0056(5) -0.0085(5) -0.0011(4) C16A 0.0240(6) 0.0204(5) 0.0246(6) -0.0022(4) -0.0068(5) 0.0018(4) O1G 0.0277(5) 0.0318(5) 0.0428(6) 0.0024(4) -0.0089(4) 0.0032(4) O2G 0.0289(5) 0.0297(5) 0.0547(7) 0.0005(5) -0.0188(5) -0.0003(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 O1 C1 1.4384(13) . ? O1 H1 0.9800(2) . ? C1 C8 1.5355(16) . ? C1 C2 1.5361(16) . ? C1 C14 1.5372(16) . ? C2 C3 1.3908(17) . ? C2 C7 1.3919(17) . ? C3 C4 1.3928(18) . ? C3 H3 0.9300 . ? C4 C5 1.383(2) . ? C4 H4 0.9300 . ? C5 C6 1.386(2) . ? C5 H5 0.9300 . ? C6 C7 1.3874(18) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C13 1.3881(17) . ? C8 C9 1.3916(17) . ? C9 C10 1.3854(18) . ? C9 H9 0.9300 . ? C10 C11 1.3849(19) . ? C10 H10 0.9300 . ? C11 C12 1.378(2) . ? C11 H11 0.9300 . ? C12 C13 1.3918(18) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C16 1.3884(16) . ? C14 C15 1.3921(16) . ? C15 C16 1.3880(17) 2_556 ? C15 H15 0.9300 . ? C16 C15 1.3880(17) 2_556 ? C16 H16 0.9300 . ? O1A C1A 1.4458(14) . ? O1A H1A 0.9750(2) . ? C1A C2A 1.5353(16) . ? C1A C8A 1.5356(16) . ? C1A C14A 1.5396(16) . ? C2A C3A 1.3907(18) . ? C2A C7A 1.3940(18) . ? C3A C4A 1.387(2) . ? C3A H3A 0.9300 . ? C4A C5A 1.383(2) . ? C4A H4A 0.9300 . ? C5A C6A 1.376(2) . ? C5A H5A 0.9300 . ? C6A C7A 1.3874(18) . ? C6A H6A 0.9300 . ? C7A H7A 0.9300 . ? C8A C13A 1.3920(17) . ? C8A C9A 1.3942(16) . ? C9A C10A 1.3885(18) . ? C9A H9A 0.9300 . ? C10A C11A 1.382(2) . ? C10A H10A 0.9300 . ? C11A C12A 1.382(2) . ? C11A H11A 0.9300 . ? C12A C13A 1.3865(18) . ? C12A H12A 0.9300 . ? C13A H13A 0.9300 . ? C14A C16A 1.3879(17) . ? C14A C15A 1.3958(16) . ? C15A C16A 1.3899(17) 2_566 ? C15A H15A 0.9300 . ? C16A C15A 1.3899(17) 2_566 ? C16A H16A 0.9300 . ? O1G H1GB 0.87(2) . ? O1G H1GA 0.9750(2) . ? O2G H2GA 0.9800(2) . ? O2G H2GB 0.9600(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 C1 O1 H1 111.8(5) . . ? O1 C1 C8 104.57(9) . . ? O1 C1 C2 109.36(9) . . ? C8 C1 C2 110.99(9) . . ? O1 C1 C14 108.51(9) . . ? C8 C1 C14 112.07(9) . . ? C2 C1 C14 111.09(9) . . ? C3 C2 C7 118.56(11) . . ? C3 C2 C1 122.19(11) . . ? C7 C2 C1 119.21(11) . . ? C2 C3 C4 120.55(12) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 120.29(13) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.58(12) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 120.12(13) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.89(12) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C13 C8 C9 118.38(11) . . ? C13 C8 C1 122.71(11) . . ? C9 C8 C1 118.91(10) . . ? C10 C9 C8 121.09(12) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 120.01(12) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 119.49(12) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 120.52(12) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C8 C13 C12 120.52(12) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C16 C14 C15 117.32(11) . . ? C16 C14 C1 122.94(10) . . ? C15 C14 C1 119.74(10) . . ? C16 C15 C14 121.45(11) 2_556 . ? C16 C15 H15 119.3 2_556 . ? C14 C15 H15 119.3 . . ? C15 C16 C14 121.23(11) 2_556 . ? C15 C16 H16 119.4 2_556 . ? C14 C16 H16 119.4 . . ? C1A O1A H1A 112.4(8) . . ? O1A C1A C2A 109.60(9) . . ? O1A C1A C8A 105.49(9) . . ? C2A C1A C8A 110.51(9) . . ? O1A C1A C14A 106.71(9) . . ? C2A C1A C14A 111.64(9) . . ? C8A C1A C14A 112.59(9) . . ? C3A C2A C7A 118.42(12) . . ? C3A C2A C1A 121.21(11) . . ? C7A C2A C1A 120.31(11) . . ? C4A C3A C2A 120.42(14) . . ? C4A C3A H3A 119.8 . . ? C2A C3A H3A 119.8 . . ? C5A C4A C3A 120.48(14) . . ? C5A C4A H4A 119.8 . . ? C3A C4A H4A 119.8 . . ? C6A C5A C4A 119.70(13) . . ? C6A C5A H5A 120.2 . . ? C4A C5A H5A 120.2 . . ? C5A C6A C7A 120.07(14) . . ? C5A C6A H6A 120.0 . . ? C7A C6A H6A 120.0 . . ? C6A C7A C2A 120.91(13) . . ? C6A C7A H7A 119.5 . . ? C2A C7A H7A 119.5 . . ? C13A C8A C9A 118.23(11) . . ? C13A C8A C1A 121.45(10) . . ? C9A C8A C1A 120.32(10) . . ? C10A C9A C8A 121.02(12) . . ? C10A C9A H9A 119.5 . . ? C8A C9A H9A 119.5 . . ? C11A C10A C9A 120.02(12) . . ? C11A C10A H10A 120.0 . . ? C9A C10A H10A 120.0 . . ? C12A C11A C10A 119.52(12) . . ? C12A C11A H11A 120.2 . . ? C10A C11A H11A 120.2 . . ? C11A C12A C13A 120.58(12) . . ? C11A C12A H12A 119.7 . . ? C13A C12A H12A 119.7 . . ? C12A C13A C8A 120.61(12) . . ? C12A C13A H13A 119.7 . . ? C8A C13A H13A 119.7 . . ? C16A C14A C15A 117.80(11) . . ? C16A C14A C1A 123.10(10) . . ? C15A C14A C1A 118.98(10) . . ? C16A C15A C14A 121.32(11) 2_566 . ? C16A C15A H15A 119.3 2_566 . ? C14A C15A H15A 119.3 . . ? C14A C16A C15A 120.88(11) . 2_566 ? C14A C16A H16A 119.6 . . ? C15A C16A H16A 119.6 2_566 . ? H1GB O1G H1GA 106.7(15) . . ? H2GA O2G H2GB 107.3(12) . . ? 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 145.35(11) . . . . ? C8 C1 C2 C3 -99.79(13) . . . . ? C14 C1 C2 C3 25.61(15) . . . . ? O1 C1 C2 C7 -36.88(14) . . . . ? C8 C1 C2 C7 77.97(13) . . . . ? C14 C1 C2 C7 -156.62(11) . . . . ? C7 C2 C3 C4 0.72(19) . . . . ? C1 C2 C3 C4 178.50(12) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C4 C5 C6 C7 0.4(2) . . . . ? C5 C6 C7 C2 -0.2(2) . . . . ? C3 C2 C7 C6 -0.36(19) . . . . ? C1 C2 C7 C6 -178.21(11) . . . . ? O1 C1 C8 C13 132.76(12) . . . . ? C2 C1 C8 C13 14.95(15) . . . . ? C14 C1 C8 C13 -109.90(13) . . . . ? O1 C1 C8 C9 -47.31(13) . . . . ? C2 C1 C8 C9 -165.12(11) . . . . ? C14 C1 C8 C9 70.03(13) . . . . ? C13 C8 C9 C10 -0.70(19) . . . . ? C1 C8 C9 C10 179.36(11) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? C9 C10 C11 C12 0.1(2) . . . . ? C10 C11 C12 C13 -0.1(2) . . . . ? C9 C8 C13 C12 0.69(19) . . . . ? C1 C8 C13 C12 -179.38(12) . . . . ? C11 C12 C13 C8 -0.3(2) . . . . ? O1 C1 C14 C16 132.77(11) . . . . ? C8 C1 C14 C16 17.82(15) . . . . ? C2 C1 C14 C16 -106.98(13) . . . . ? O1 C1 C14 C15 -47.92(14) . . . . ? C8 C1 C14 C15 -162.87(11) . . . . ? C2 C1 C14 C15 72.33(13) . . . . ? C16 C14 C15 C16 -0.2(2) . . . 2_556 ? C1 C14 C15 C16 -179.55(11) . . . 2_556 ? C15 C14 C16 C15 0.2(2) . . . 2_556 ? C1 C14 C16 C15 179.53(11) . . . 2_556 ? O1A C1A C2A C3A -152.63(11) . . . . ? C8A C1A C2A C3A 91.52(13) . . . . ? C14A C1A C2A C3A -34.62(15) . . . . ? O1A C1A C2A C7A 30.20(14) . . . . ? C8A C1A C2A C7A -85.65(13) . . . . ? C14A C1A C2A C7A 148.21(11) . . . . ? C7A C2A C3A C4A -0.6(2) . . . . ? C1A C2A C3A C4A -177.78(12) . . . . ? C2A C3A C4A C5A -0.5(2) . . . . ? C3A C4A C5A C6A 1.0(2) . . . . ? C4A C5A C6A C7A -0.5(2) . . . . ? C5A C6A C7A C2A -0.6(2) . . . . ? C3A C2A C7A C6A 1.08(19) . . . . ? C1A C2A C7A C6A 178.33(11) . . . . ? O1A C1A C8A C13A -148.99(11) . . . . ? C2A C1A C8A C13A -30.61(15) . . . . ? C14A C1A C8A C13A 95.00(13) . . . . ? O1A C1A C8A C9A 31.56(14) . . . . ? C2A C1A C8A C9A 149.95(11) . . . . ? C14A C1A C8A C9A -84.45(13) . . . . ? C13A C8A C9A C10A 0.40(18) . . . . ? C1A C8A C9A C10A 179.86(11) . . . . ? C8A C9A C10A C11A 0.8(2) . . . . ? C9A C10A C11A C12A -1.1(2) . . . . ? C10A C11A C12A C13A 0.3(2) . . . . ? C11A C12A C13A C8A 0.9(2) . . . . ? C9A C8A C13A C12A -1.23(19) . . . . ? C1A C8A C13A C12A 179.31(12) . . . . ? O1A C1A C14A C16A -107.38(12) . . . . ? C2A C1A C14A C16A 132.89(12) . . . . ? C8A C1A C14A C16A 7.90(15) . . . . ? O1A C1A C14A C15A 68.56(12) . . . . ? C2A C1A C14A C15A -51.17(14) . . . . ? C8A C1A C14A C15A -176.16(10) . . . . ? C16A C14A C15A C16A 0.03(19) . . . 2_566 ? C1A C14A C15A C16A -176.13(11) . . . 2_566 ? C15A C14A C16A C15A -0.03(19) . . . 2_566 ? C1A C14A C16A C15A 175.96(11) . . . 2_566 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.51 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.292 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.036