Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Ayesha Jacobs' 'M. Caira' 'Luigi R. Nassimbeni' 'Fumio Toda' _publ_contact_author_name 'Dr Ayesha Jacobs' _publ_contact_author_address ; Department of Chemistry University of Port Elizabeth 6031 Port Elizabeth SOUTH AFRICA ; _publ_contact_author_email CHAAAJ@UPE.AC.ZA _publ_section_title ; Complexation with diol host compounds. Part 34 Inclusion compounds of 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol with DMF and DMSO: structures, selectivity and kinetics of desolvation. ; data_c:\t7dmf _database_code_CSD 205550 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol dimethyl formamide clathrate ; _chemical_name_common ;1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol dimethyl formamide clathrate ; _chemical_formula_moiety 'C30 H22 O2.2(C3 H7 N O)' _chemical_formula_sum 'C36 H36 N2 O4' _chemical_formula_weight 560.67 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 11.564(2) _cell_length_b 16.393(3) _cell_length_c 16.793(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3183.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.44 _exptl_crystal_density_diffrn 1.170 _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.076 _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 9742 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 26.45 _reflns_number_total 3248 _reflns_number_gt 2161 _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^)+(0.1055P)^2^+0.7550P] 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 3248 _refine_ls_number_parameters 196 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0979 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.2048 _refine_ls_wR_factor_gt 0.1802 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.353 _refine_ls_shift/su_mean 0.057 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 0.17111(16) 0.02344(9) 0.57392(9) 0.0729(5) Uani 1 1 d D . . C1 C 0.24918(17) -0.04055(12) 0.59365(11) 0.0526(5) Uani 1 1 d . . . H1 H 0.1576(19) 0.0647(13) 0.6168(10) 0.123(11) Uiso 1 1 d D . . C2 C 0.3614(2) -0.02330(13) 0.55417(12) 0.0626(6) Uani 1 1 d . . . C3 C 0.4491(2) -0.00871(14) 0.51961(12) 0.0649(6) Uani 1 1 d . . . C11 C 0.20166(16) -0.11969(12) 0.55860(11) 0.0518(5) Uani 1 1 d . . . C12 C 0.10401(19) -0.11938(15) 0.51038(14) 0.0687(6) Uani 1 1 d . . . H12 H 0.0653 -0.0695 0.4995 0.082 Uiso 1 1 calc R . . C13 C 0.0630(3) -0.1915(2) 0.47819(17) 0.0923(9) Uani 1 1 d . . . H13 H -0.0040 -0.1906 0.4455 0.111 Uiso 1 1 calc R . . C14 C 0.1170(3) -0.26316(19) 0.49264(19) 0.0978(9) Uani 1 1 d . . . H14 H 0.0881 -0.3122 0.4699 0.117 Uiso 1 1 calc R . . C15 C 0.2138(3) -0.26506(16) 0.54032(19) 0.0893(8) Uani 1 1 d . . . H15 H 0.2516 -0.3154 0.5509 0.107 Uiso 1 1 calc R . . C16 C 0.2557(2) -0.19355(13) 0.57273(14) 0.0679(6) Uani 1 1 d . . . H16 H 0.3228 -0.1951 0.6053 0.082 Uiso 1 1 calc R . . C21 C 0.26384(17) -0.04590(12) 0.68446(12) 0.0549(5) Uani 1 1 d . . . C22 C 0.1742(2) -0.07544(17) 0.72981(13) 0.0756(7) Uani 1 1 d . . . H22 H 0.1068 -0.0958 0.7043 0.091 Uiso 1 1 calc R . . C23 C 0.1806(3) -0.0759(2) 0.81214(15) 0.0942(9) Uani 1 1 d . . . H23 H 0.1172 -0.0960 0.8423 0.113 Uiso 1 1 calc R . . C24 C 0.2764(3) -0.0480(2) 0.85051(15) 0.0941(9) Uani 1 1 d . . . H24 H 0.2812 -0.0497 0.9070 0.113 Uiso 1 1 calc R . . C25 C 0.3654(2) -0.0176(2) 0.80627(15) 0.0980(10) Uani 1 1 d . . . H25 H 0.4323 0.0030 0.8322 0.118 Uiso 1 1 calc R . . C26 C 0.3593(2) -0.01635(19) 0.72375(14) 0.0807(8) Uani 1 1 d . . . H26 H 0.4221 0.0052 0.6940 0.097 Uiso 1 1 calc R . . O1G O 0.3833(3) -0.36305(17) 0.67632(12) 0.1573(13) Uani 1 1 d . . . C2G C 0.3567(3) -0.3577(2) 0.7445(2) 0.1052(10) Uani 1 1 d . . . H2G H 0.2940 -0.3909 0.7613 0.126 Uiso 1 1 calc R . . N3G N 0.4024(2) -0.31262(14) 0.79761(13) 0.0869(7) Uani 1 1 d . . . C4G C 0.3668(5) -0.3093(4) 0.8792(2) 0.213(3) Uani 1 1 d . . . H4GA H 0.2877 -0.3302 0.8840 0.319 Uiso 1 1 calc R . . H4GC H 0.3693 -0.2526 0.8979 0.319 Uiso 1 1 calc R . . H4GB H 0.4189 -0.3427 0.9117 0.319 Uiso 1 1 calc R . . C5G C 0.4977(5) -0.2602(4) 0.7762(3) 0.214(3) Uani 1 1 d . . . H5GA H 0.5706 -0.2858 0.7924 0.321 Uiso 1 1 calc R . . H5GC H 0.4893 -0.2076 0.8032 0.321 Uiso 1 1 calc R . . H5GB H 0.4979 -0.2517 0.7184 0.321 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0941(12) 0.0620(9) 0.0626(9) 0.0020(7) -0.0068(8) 0.0183(8) C1 0.0539(11) 0.0572(11) 0.0468(10) 0.0040(8) 0.0050(9) -0.0001(9) C2 0.0699(14) 0.0684(13) 0.0494(11) 0.0029(9) 0.0044(10) -0.0131(11) C3 0.0684(13) 0.0778(14) 0.0484(11) 0.0053(10) 0.0064(10) -0.0174(11) C11 0.0512(10) 0.0599(11) 0.0444(9) 0.0035(8) 0.0083(8) -0.0007(9) C12 0.0665(13) 0.0760(14) 0.0637(13) 0.0017(11) -0.0066(11) -0.0021(11) C13 0.0928(19) 0.102(2) 0.0818(18) -0.0100(15) -0.0180(15) -0.0242(17) C14 0.124(2) 0.084(2) 0.0859(19) -0.0187(15) 0.0056(19) -0.0286(18) C15 0.116(2) 0.0596(15) 0.0924(19) -0.0029(13) 0.0151(18) 0.0044(14) C16 0.0704(14) 0.0631(13) 0.0703(14) 0.0029(10) 0.0015(11) 0.0058(11) C21 0.0544(11) 0.0630(12) 0.0473(10) 0.0000(8) 0.0044(9) 0.0010(9) C22 0.0770(15) 0.0964(17) 0.0534(12) 0.0063(11) 0.0072(11) -0.0204(13) C23 0.1010(19) 0.125(2) 0.0561(14) 0.0084(14) 0.0172(14) -0.0192(18) C24 0.102(2) 0.134(3) 0.0470(12) -0.0015(14) -0.0019(14) 0.0140(18) C25 0.0734(16) 0.159(3) 0.0619(15) -0.0213(17) -0.0107(14) 0.0034(17) C26 0.0584(13) 0.125(2) 0.0584(13) -0.0077(13) 0.0042(11) -0.0073(14) O1G 0.254(3) 0.154(2) 0.0645(13) -0.0227(13) 0.0115(16) -0.107(2) C2G 0.133(3) 0.099(2) 0.084(2) -0.0068(17) -0.0064(19) -0.037(2) N3G 0.1082(17) 0.0911(15) 0.0616(12) -0.0133(11) -0.0007(12) -0.0243(13) C4G 0.259(7) 0.284(8) 0.095(3) -0.065(4) 0.059(4) -0.114(6) C5G 0.250(7) 0.256(7) 0.136(4) -0.020(4) 0.002(4) -0.169(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.423(2) . ? O1 H1 1.0003(10) . ? C1 C2 1.484(3) . ? C1 C11 1.527(3) . ? C1 C21 1.537(3) . ? C2 C3 1.193(3) . ? C3 C3 1.379(4) 5_656 ? C11 C16 1.383(3) . ? C11 C12 1.389(3) . ? C12 C13 1.383(4) . ? C12 H12 0.9300 . ? C13 C14 1.352(4) . ? C13 H13 0.9300 . ? C14 C15 1.376(4) . ? C14 H14 0.9300 . ? C15 C16 1.380(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C22 1.374(3) . ? C21 C26 1.374(3) . ? C22 C23 1.384(3) . ? C22 H22 0.9300 . ? C23 C24 1.360(4) . ? C23 H23 0.9300 . ? C24 C25 1.364(4) . ? C24 H24 0.9300 . ? C25 C26 1.387(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? O1G C2G 1.188(4) . ? C2G N3G 1.273(4) . ? C2G H2G 0.9300 . ? N3G C4G 1.433(4) . ? N3G C5G 1.442(5) . ? C4G H4GA 0.9600 . ? C4G H4GC 0.9600 . ? C4G H4GB 0.9600 . ? C5G H5GA 0.9600 . ? C5G H5GC 0.9600 . ? C5G H5GB 0.9600 . ? 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 115.4(9) . . ? O1 C1 C2 108.07(16) . . ? O1 C1 C11 107.96(16) . . ? C2 C1 C11 107.71(16) . . ? O1 C1 C21 110.06(15) . . ? C2 C1 C21 110.96(16) . . ? C11 C1 C21 111.94(15) . . ? C3 C2 C1 177.3(2) . . ? C2 C3 C3 179.3(3) . 5_656 ? C16 C11 C12 118.0(2) . . ? C16 C11 C1 121.02(18) . . ? C12 C11 C1 120.94(18) . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 121.0(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.2 . . ? C15 C16 C11 121.2(2) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C22 C21 C26 117.7(2) . . ? C22 C21 C1 119.12(18) . . ? C26 C21 C1 123.01(19) . . ? C21 C22 C23 121.0(2) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 121.0(3) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 118.6(2) . . ? C23 C24 H24 120.7 . . ? C25 C24 H24 120.7 . . ? C24 C25 C26 120.7(3) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C21 C26 C25 121.0(2) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? O1G C2G N3G 127.7(3) . . ? O1G C2G H2G 116.2 . . ? N3G C2G H2G 116.2 . . ? C2G N3G C4G 125.0(3) . . ? C2G N3G C5G 119.2(3) . . ? C4G N3G C5G 115.8(3) . . ? N3G C4G H4GA 109.5 . . ? N3G C4G H4GC 109.5 . . ? H4GA C4G H4GC 109.5 . . ? N3G C4G H4GB 109.4 . . ? H4GA C4G H4GB 109.5 . . ? H4GC C4G H4GB 109.5 . . ? N3G C5G H5GA 109.5 . . ? N3G C5G H5GC 109.5 . . ? H5GA C5G H5GC 109.5 . . ? N3G C5G H5GB 109.5 . . ? H5GA C5G H5GB 109.5 . . ? H5GC C5G H5GB 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 -46(5) . . . . ? C11 C1 C2 C3 71(5) . . . . ? C21 C1 C2 C3 -166(5) . . . . ? C1 C2 C3 C3 133(33) . . . 5_656 ? O1 C1 C11 C16 -175.70(18) . . . . ? C2 C1 C11 C16 67.8(2) . . . . ? C21 C1 C11 C16 -54.4(2) . . . . ? O1 C1 C11 C12 5.5(2) . . . . ? C2 C1 C11 C12 -111.0(2) . . . . ? C21 C1 C11 C12 126.74(19) . . . . ? C16 C11 C12 C13 0.2(3) . . . . ? C1 C11 C12 C13 179.1(2) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C13 C14 C15 C16 -0.4(5) . . . . ? C14 C15 C16 C11 0.4(4) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? C1 C11 C16 C15 -179.2(2) . . . . ? O1 C1 C21 C22 71.7(3) . . . . ? C2 C1 C21 C22 -168.7(2) . . . . ? C11 C1 C21 C22 -48.3(3) . . . . ? O1 C1 C21 C26 -102.8(2) . . . . ? C2 C1 C21 C26 16.8(3) . . . . ? C11 C1 C21 C26 137.1(2) . . . . ? C26 C21 C22 C23 -0.5(4) . . . . ? C1 C21 C22 C23 -175.4(2) . . . . ? C21 C22 C23 C24 -0.8(5) . . . . ? C22 C23 C24 C25 1.6(5) . . . . ? C23 C24 C25 C26 -1.1(5) . . . . ? C22 C21 C26 C25 1.0(4) . . . . ? C1 C21 C26 C25 175.6(3) . . . . ? C24 C25 C26 C21 -0.2(5) . . . . ? O1G C2G N3G C4G -179.6(5) . . . . ? O1G C2G N3G C5G 0.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.348 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.042 #===END data_c:\t7dmso _database_code_CSD 205551 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol dimethylsulphoxide clathrate ; _chemical_name_common ;1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol dimethylsulphoxide clathrate ; _chemical_formula_moiety 'C30 H22 O2.2(C2 H6 S O)' _chemical_formula_sum 'C34 H34 O4 S2' _chemical_formula_weight 570.73 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' S S 0.1246 0.1234 '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 11.377(2) _cell_length_b 15.982(3) _cell_length_c 16.191(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2944.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_description plate-like _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.218 _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 5047 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2694 _reflns_number_gt 2286 _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^)+(0.0000P)^2^+19.1966P] 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 2694 _refine_ls_number_parameters 184 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1096 _refine_ls_R_factor_gt 0.0970 _refine_ls_wR_factor_ref 0.2108 _refine_ls_wR_factor_gt 0.2060 _refine_ls_goodness_of_fit_ref 1.226 _refine_ls_restrained_S_all 1.225 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.007 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8323(3) 0.02747(18) 0.41586(18) 0.0232(8) Uani 1 1 d D . . C1 C 0.7549(4) -0.0411(3) 0.4011(3) 0.0189(10) Uani 1 1 d . . . C2 C 0.6414(4) -0.0250(3) 0.4440(3) 0.0202(10) Uani 1 1 d . . . C3 C 0.5519(4) -0.0094(3) 0.4798(3) 0.0220(10) Uani 1 1 d . . . C11 C 0.7354(4) -0.0510(3) 0.3077(3) 0.0194(10) Uani 1 1 d . . . C12 C 0.8241(5) -0.0816(3) 0.2594(3) 0.0413(15) Uani 1 1 d . . . H12 H 0.8929 -0.1003 0.2843 0.050 Uiso 1 1 calc R . . H1 H 0.8213 0.0645 0.3683 0.07(2) Uiso 1 1 d RD . . C13 C 0.8140(6) -0.0856(5) 0.1742(4) 0.0507(18) Uani 1 1 d . . . H13 H 0.8759 -0.1065 0.1428 0.061 Uiso 1 1 calc R . . C14 C 0.7137(5) -0.0589(3) 0.1362(3) 0.0338(13) Uani 1 1 d . . . H14 H 0.7062 -0.0622 0.0791 0.041 Uiso 1 1 calc R . . C15 C 0.6250(5) -0.0275(5) 0.1830(3) 0.0475(17) Uani 1 1 d . . . H15 H 0.5567 -0.0084 0.1577 0.057 Uiso 1 1 calc R . . C16 C 0.6354(5) -0.0237(4) 0.2686(3) 0.0390(14) Uani 1 1 d . . . H16 H 0.5737 -0.0024 0.2998 0.047 Uiso 1 1 calc R . . C21 C 0.8118(4) -0.1197(3) 0.4392(3) 0.0181(10) Uani 1 1 d . . . C22 C 0.9141(4) -0.1138(3) 0.4856(3) 0.0241(11) Uani 1 1 d . . . H22 H 0.9485 -0.0618 0.4945 0.029 Uiso 1 1 calc R . . C23 C 0.9652(5) -0.1851(3) 0.5187(3) 0.0327(12) Uani 1 1 d . . . H23 H 1.0337 -0.1806 0.5498 0.039 Uiso 1 1 calc R . . C24 C 0.9149(5) -0.2635(3) 0.5057(3) 0.0330(13) Uani 1 1 d . . . H24 H 0.9503 -0.3115 0.5267 0.040 Uiso 1 1 calc R . . C25 C 0.8125(5) -0.2688(3) 0.4616(3) 0.0331(13) Uani 1 1 d . . . H25 H 0.7769 -0.3207 0.4544 0.040 Uiso 1 1 calc R . . C26 C 0.7609(4) -0.1984(3) 0.4274(3) 0.0253(11) Uani 1 1 d . . . H26 H 0.6923 -0.2035 0.3966 0.030 Uiso 1 1 calc R . . S1G S 0.40142(15) 0.14520(11) 0.27119(10) 0.0475(5) Uani 1 1 d . . . O2G O 0.3284(4) 0.1514(2) 0.1952(2) 0.0473(11) Uani 1 1 d . . . C3G C 0.4933(9) 0.2361(8) 0.2690(6) 0.130(5) Uani 1 1 d . . . H3GB H 0.5276 0.2419 0.2151 0.195 Uiso 1 1 calc R . . H3GC H 0.5546 0.2304 0.3093 0.195 Uiso 1 1 calc R . . H3GA H 0.4471 0.2848 0.2813 0.195 Uiso 1 1 calc R . . C4G C 0.3183(8) 0.1800(6) 0.3557(5) 0.082(3) Uani 1 1 d . . . H4GA H 0.2904 0.2357 0.3451 0.123 Uiso 1 1 calc R . . H4GC H 0.3664 0.1801 0.4044 0.123 Uiso 1 1 calc R . . H4GB H 0.2525 0.1433 0.3638 0.123 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0238(18) 0.0160(16) 0.0298(18) -0.0028(15) 0.0000(15) -0.0044(14) C1 0.018(2) 0.019(2) 0.020(2) -0.0030(19) 0.0028(19) -0.0056(19) C2 0.023(2) 0.018(2) 0.019(2) -0.0037(19) 0.001(2) 0.001(2) C3 0.022(2) 0.022(2) 0.023(2) -0.004(2) 0.001(2) -0.004(2) C11 0.019(2) 0.015(2) 0.024(2) -0.0011(19) 0.005(2) -0.0028(19) C12 0.028(3) 0.067(4) 0.029(3) -0.017(3) -0.002(2) 0.019(3) C13 0.045(4) 0.080(5) 0.027(3) -0.020(3) 0.003(3) 0.023(4) C14 0.041(3) 0.038(3) 0.022(3) -0.003(2) 0.000(2) -0.010(3) C15 0.035(3) 0.082(5) 0.025(3) 0.016(3) -0.004(3) 0.010(3) C16 0.030(3) 0.060(4) 0.027(3) 0.012(3) 0.005(2) 0.018(3) C21 0.017(2) 0.019(2) 0.019(2) -0.0012(18) 0.0063(18) -0.0018(19) C22 0.023(2) 0.021(2) 0.028(3) -0.001(2) -0.001(2) -0.002(2) C23 0.027(3) 0.033(3) 0.038(3) 0.008(2) -0.004(2) 0.001(2) C24 0.038(3) 0.021(3) 0.040(3) 0.007(2) 0.008(3) 0.008(2) C25 0.037(3) 0.015(3) 0.047(3) -0.005(2) 0.006(3) -0.007(2) C26 0.022(2) 0.022(2) 0.032(3) -0.002(2) -0.003(2) -0.005(2) S1G 0.0471(9) 0.0549(10) 0.0406(9) -0.0061(7) -0.0055(7) 0.0128(8) O2G 0.071(3) 0.036(2) 0.035(2) -0.0020(18) -0.016(2) -0.012(2) C3G 0.105(8) 0.215(13) 0.071(6) -0.006(7) -0.007(6) -0.114(9) C4G 0.087(6) 0.096(7) 0.064(5) -0.026(5) 0.024(5) -0.014(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 1.426(5) . ? O1 H1 0.9789 . ? C1 C2 1.489(6) . ? C1 C11 1.538(6) . ? C1 C21 1.541(6) . ? C2 C3 1.197(7) . ? C3 C3 1.384(9) 5_656 ? C11 C12 1.367(7) . ? C11 C16 1.373(7) . ? C12 C13 1.385(7) . ? C12 H12 0.9300 . ? C13 C14 1.365(8) . ? C13 H13 0.9300 . ? C14 C15 1.358(8) . ? C14 H14 0.9300 . ? C15 C16 1.391(8) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C22 1.389(7) . ? C21 C26 1.398(6) . ? C22 C23 1.388(7) . ? C22 H22 0.9300 . ? C23 C24 1.393(8) . ? C23 H23 0.9300 . ? C24 C25 1.369(8) . ? C24 H24 0.9300 . ? C25 C26 1.385(7) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? S1G O2G 1.487(4) . ? S1G C4G 1.754(8) . ? S1G C3G 1.790(9) . ? C3G H3GB 0.9600 . ? C3G H3GC 0.9600 . ? C3G H3GA 0.9600 . ? C4G H4GA 0.9600 . ? C4G H4GC 0.9600 . ? C4G H4GB 0.9600 . ? 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 104.8 . . ? O1 C1 C2 109.0(4) . . ? O1 C1 C11 109.4(3) . . ? C2 C1 C11 110.6(4) . . ? O1 C1 C21 107.5(4) . . ? C2 C1 C21 108.6(4) . . ? C11 C1 C21 111.7(4) . . ? C3 C2 C1 177.5(5) . . ? C2 C3 C3 179.2(7) . 5_656 ? C12 C11 C16 117.5(4) . . ? C12 C11 C1 119.6(4) . . ? C16 C11 C1 122.7(4) . . ? C11 C12 C13 121.7(5) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 120.2(5) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 119.0(5) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 120.6(5) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 121.0(5) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C22 C21 C26 118.8(4) . . ? C22 C21 C1 120.9(4) . . ? C26 C21 C1 120.3(4) . . ? C23 C22 C21 120.3(5) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 120.5(5) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 119.0(5) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 121.3(5) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C25 C26 C21 120.1(5) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? O2G S1G C4G 108.8(4) . . ? O2G S1G C3G 104.8(4) . . ? C4G S1G C3G 94.2(5) . . ? S1G C3G H3GB 109.5 . . ? S1G C3G H3GC 109.5 . . ? H3GB C3G H3GC 109.5 . . ? S1G C3G H3GA 109.5 . . ? H3GB C3G H3GA 109.5 . . ? H3GC C3G H3GA 109.5 . . ? S1G C4G H4GA 109.5 . . ? S1G C4G H4GC 109.5 . . ? H4GA C4G H4GC 109.5 . . ? S1G C4G H4GB 109.5 . . ? H4GA C4G H4GB 109.5 . . ? H4GC C4G H4GB 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 -5(12) . . . . ? C11 C1 C2 C3 -125(12) . . . . ? C21 C1 C2 C3 112(12) . . . . ? C1 C2 C3 C3 83(56) . . . 5_656 ? O1 C1 C11 C12 72.4(5) . . . . ? C2 C1 C11 C12 -167.6(4) . . . . ? C21 C1 C11 C12 -46.5(6) . . . . ? O1 C1 C11 C16 -102.0(5) . . . . ? C2 C1 C11 C16 18.0(7) . . . . ? C21 C1 C11 C16 139.1(5) . . . . ? C16 C11 C12 C13 -0.3(8) . . . . ? C1 C11 C12 C13 -174.9(5) . . . . ? C11 C12 C13 C14 -0.3(10) . . . . ? C12 C13 C14 C15 0.9(10) . . . . ? C13 C14 C15 C16 -0.9(10) . . . . ? C12 C11 C16 C15 0.2(9) . . . . ? C1 C11 C16 C15 174.7(6) . . . . ? C14 C15 C16 C11 0.4(11) . . . . ? O1 C1 C21 C22 6.1(6) . . . . ? C2 C1 C21 C22 -111.6(5) . . . . ? C11 C1 C21 C22 126.2(4) . . . . ? O1 C1 C21 C26 -173.9(4) . . . . ? C2 C1 C21 C26 68.4(5) . . . . ? C11 C1 C21 C26 -53.9(6) . . . . ? C26 C21 C22 C23 0.8(7) . . . . ? C1 C21 C22 C23 -179.3(5) . . . . ? C21 C22 C23 C24 0.1(8) . . . . ? C22 C23 C24 C25 -1.7(8) . . . . ? C23 C24 C25 C26 2.3(8) . . . . ? C24 C25 C26 C21 -1.5(8) . . . . ? C22 C21 C26 C25 -0.1(7) . . . . ? C1 C21 C26 C25 179.9(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.496 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.091