# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Cameron Jones' 'Shaun P. Green' 'Richard P. Rose' 'Andreas Stasch' _publ_contact_author_name 'Cameron Jones' _publ_contact_author_address ; Chemistry Department Cardiff University PO Box 912 Park Place Cardiff CF10 3TB UNITED KINGDOM ; _publ_contact_author_email JONESCA6@CARDIFF.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; GaI: A New Reagent for Chemo- and Diastereoselective C-C Bond Forming Reactions ; # Attachment 'cmpd1a.CIF' data_compound1a _database_code_depnum_ccdc_archive 'CCDC 626737' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H26 O3' _chemical_formula_weight 422.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 32.142(6) _cell_length_b 6.2276(12) _cell_length_c 11.413(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.70(3) _cell_angle_gamma 90.00 _cell_volume 2237.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5064 _diffrn_reflns_av_R_equivalents 0.1064 _diffrn_reflns_av_sigmaI/netI 0.1841 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.76 _diffrn_reflns_theta_max 24.81 _reflns_number_total 3292 _reflns_number_gt 2149 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The relatively high r-factor of the structure is a result of the reflection data being very weak above theta angle of 22 degrees. ; _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^)+(0.0284P)^2^+1.2539P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 3292 _refine_ls_number_parameters 292 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1474 _refine_ls_R_factor_gt 0.0876 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1387 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.067 _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 0.07373(11) 0.0558(6) 0.5592(3) 0.0353(10) Uani 1 1 d . . . O2 O 0.13663(12) -0.1401(5) 0.7575(3) 0.0304(9) Uani 1 1 d . . . H2 H 0.1165 -0.2102 0.7163 0.037 Uiso 1 1 calc R . . O3 O 0.08862(12) 0.4990(6) 0.6831(3) 0.0368(10) Uani 1 1 d . . . C1 C 0.11820(17) 0.1035(8) 0.5880(4) 0.0285(13) Uani 1 1 d . . . H1 H 0.1224 0.2562 0.5659 0.034 Uiso 1 1 calc R . . C2 C 0.13194(16) 0.0804(7) 0.7267(4) 0.0254(12) Uani 1 1 d . . . C3 C 0.09704(17) 0.1690(8) 0.7912(4) 0.0260(12) Uani 1 1 d . . . H3 H 0.0747 0.0547 0.7805 0.031 Uiso 1 1 calc R . . C4 C 0.07345(18) 0.3727(9) 0.7436(4) 0.0299(13) Uani 1 1 d . . . C5 C 0.0539(2) 0.1509(11) 0.4465(5) 0.0486(17) Uani 1 1 d . . . H5A H 0.0559 0.3077 0.4529 0.073 Uiso 1 1 calc R . . H5B H 0.0240 0.1082 0.4263 0.073 Uiso 1 1 calc R . . H5C H 0.0685 0.1015 0.3838 0.073 Uiso 1 1 calc R . . C6 C 0.14307(16) -0.0386(8) 0.5204(4) 0.0272(13) Uani 1 1 d . . . C7 C 0.1276(2) -0.2335(9) 0.4745(5) 0.0338(15) Uani 1 1 d . . . H7 H 0.1003 -0.2789 0.4842 0.041 Uiso 1 1 calc R . . C8 C 0.1509(2) -0.3653(9) 0.4142(5) 0.0419(17) Uani 1 1 d . . . H8 H 0.1394 -0.4986 0.3826 0.050 Uiso 1 1 calc R . . C9 C 0.1905(2) -0.3046(11) 0.3999(5) 0.0456(16) Uani 1 1 d . . . H9 H 0.2065 -0.3963 0.3592 0.055 Uiso 1 1 calc R . . C10 C 0.20740(19) -0.1081(11) 0.4451(4) 0.0398(15) Uani 1 1 d . . . H10 H 0.2349 -0.0652 0.4361 0.048 Uiso 1 1 calc R . . C11 C 0.18335(18) 0.0235(10) 0.5033(5) 0.0346(14) Uani 1 1 d . . . H11 H 0.1944 0.1591 0.5324 0.041 Uiso 1 1 calc R . . C12 C 0.17588(16) 0.1837(9) 0.7698(4) 0.0255(12) Uani 1 1 d . . . C13 C 0.20696(19) 0.0683(10) 0.8470(5) 0.0364(15) Uani 1 1 d . . . H13 H 0.2008 -0.0711 0.8728 0.044 Uiso 1 1 calc R . . C14 C 0.24722(19) 0.1579(11) 0.8865(5) 0.0458(16) Uani 1 1 d . . . H14 H 0.2686 0.0775 0.9377 0.055 Uiso 1 1 calc R . . C15 C 0.25612(19) 0.3598(12) 0.8521(5) 0.0458(17) Uani 1 1 d . . . H15 H 0.2835 0.4199 0.8799 0.055 Uiso 1 1 calc R . . C16 C 0.2252(2) 0.4768(10) 0.7768(5) 0.0397(15) Uani 1 1 d . . . H16 H 0.2314 0.6169 0.7521 0.048 Uiso 1 1 calc R . . C17 C 0.18524(18) 0.3894(9) 0.7375(4) 0.0307(13) Uani 1 1 d . . . H17 H 0.1639 0.4720 0.6875 0.037 Uiso 1 1 calc R . . C18 C 0.11327(16) 0.1841(9) 0.9263(4) 0.0271(13) Uani 1 1 d . . . C19 C 0.13291(17) 0.3670(10) 0.9789(5) 0.0316(13) Uani 1 1 d . . . H19 H 0.1355 0.4886 0.9306 0.038 Uiso 1 1 calc R . . C20 C 0.14883(18) 0.3760(11) 1.1009(5) 0.0397(15) Uani 1 1 d . . . H20 H 0.1616 0.5043 1.1362 0.048 Uiso 1 1 calc R . . C21 C 0.14611(19) 0.1995(11) 1.1704(5) 0.0427(16) Uani 1 1 d . . . H21 H 0.1577 0.2050 1.2538 0.051 Uiso 1 1 calc R . . C22 C 0.12672(18) 0.0132(11) 1.1206(5) 0.0383(15) Uani 1 1 d . . . H22 H 0.1246 -0.1088 1.1691 0.046 Uiso 1 1 calc R . . C23 C 0.11041(17) 0.0082(10) 0.9983(5) 0.0358(15) Uani 1 1 d . . . H23 H 0.0970 -0.1188 0.9633 0.043 Uiso 1 1 calc R . . C24 C 0.03122(17) 0.4188(9) 0.7743(4) 0.0278(13) Uani 1 1 d . . . C25 C 0.0134(2) 0.6197(10) 0.7423(6) 0.0512(18) Uani 1 1 d . . . H25 H 0.0277 0.7189 0.7010 0.061 Uiso 1 1 calc R . . C26 C -0.0251(2) 0.6746(13) 0.7707(7) 0.067(2) Uani 1 1 d . . . H26 H -0.0370 0.8128 0.7509 0.080 Uiso 1 1 calc R . . C27 C -0.0460(2) 0.5290(13) 0.8274(6) 0.0575(19) Uani 1 1 d . . . H27 H -0.0725 0.5663 0.8467 0.069 Uiso 1 1 calc R . . C28 C -0.0292(2) 0.3317(12) 0.8562(6) 0.0498(18) Uani 1 1 d . . . H28 H -0.0444 0.2310 0.8941 0.060 Uiso 1 1 calc R . . C29 C 0.0093(2) 0.2753(10) 0.8313(5) 0.0425(16) Uani 1 1 d . . . H29 H 0.0210 0.1374 0.8533 0.051 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 0.030(2) 0.045(3) 0.029(2) 0.0019(18) 0.0028(17) 0.0007(19) O2 0.039(2) 0.023(2) 0.029(2) -0.0012(17) 0.0035(17) 0.0005(18) O3 0.036(2) 0.027(2) 0.050(2) 0.0003(19) 0.014(2) -0.0046(19) C1 0.029(3) 0.026(3) 0.031(3) -0.003(2) 0.006(3) -0.005(2) C2 0.027(3) 0.015(3) 0.033(3) 0.004(2) 0.003(2) 0.000(2) C3 0.029(3) 0.022(3) 0.027(3) 0.001(2) 0.005(2) 0.000(3) C4 0.040(4) 0.022(3) 0.025(3) -0.005(3) 0.000(3) -0.007(3) C5 0.043(4) 0.065(5) 0.033(3) -0.002(3) -0.004(3) 0.013(3) C6 0.027(3) 0.031(3) 0.023(3) 0.003(2) 0.003(2) 0.006(3) C7 0.047(4) 0.032(3) 0.025(3) 0.001(3) 0.013(3) -0.004(3) C8 0.070(5) 0.032(4) 0.025(3) -0.003(2) 0.014(3) 0.003(3) C9 0.051(5) 0.054(4) 0.032(3) -0.002(3) 0.009(3) 0.018(4) C10 0.033(4) 0.060(4) 0.028(3) -0.005(3) 0.010(3) 0.009(3) C11 0.037(4) 0.041(4) 0.026(3) -0.006(3) 0.007(3) -0.006(3) C12 0.029(3) 0.024(3) 0.024(3) -0.001(3) 0.005(2) 0.002(3) C13 0.038(4) 0.045(4) 0.028(3) 0.002(3) 0.012(3) -0.003(3) C14 0.033(4) 0.063(5) 0.038(3) 0.012(3) 0.001(3) -0.003(4) C15 0.029(4) 0.070(5) 0.040(4) -0.018(4) 0.010(3) -0.017(4) C16 0.041(4) 0.038(4) 0.045(4) -0.010(3) 0.019(3) -0.011(3) C17 0.030(3) 0.029(3) 0.034(3) -0.004(3) 0.007(3) 0.002(3) C18 0.024(3) 0.033(3) 0.026(3) 0.001(3) 0.007(2) 0.006(3) C19 0.033(3) 0.031(3) 0.033(3) -0.004(3) 0.011(3) 0.005(3) C20 0.038(4) 0.043(4) 0.038(4) -0.015(3) 0.007(3) -0.001(3) C21 0.036(4) 0.059(4) 0.029(3) -0.004(3) -0.003(3) 0.019(4) C22 0.037(4) 0.042(4) 0.037(4) 0.001(3) 0.011(3) 0.022(3) C23 0.030(3) 0.042(4) 0.035(3) -0.006(3) 0.005(3) 0.003(3) C24 0.020(3) 0.039(4) 0.024(3) -0.004(2) 0.004(2) -0.001(3) C25 0.040(4) 0.041(4) 0.069(5) 0.005(3) 0.003(3) 0.002(3) C26 0.044(5) 0.054(5) 0.102(6) 0.003(4) 0.017(4) 0.013(4) C27 0.028(4) 0.065(5) 0.081(5) 0.000(4) 0.015(4) 0.007(4) C28 0.031(4) 0.071(5) 0.047(4) 0.001(3) 0.007(3) -0.004(4) C29 0.041(4) 0.048(4) 0.036(4) 0.003(3) 0.003(3) 0.002(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 1.431(6) . ? O1 C5 1.441(6) . ? O2 C2 1.418(6) . ? O3 C4 1.212(6) . ? C1 C6 1.506(7) . ? C1 C2 1.561(7) . ? C2 C12 1.539(7) . ? C2 C3 1.562(7) . ? C3 C4 1.521(8) . ? C3 C18 1.526(6) . ? C4 C24 1.497(7) . ? C6 C7 1.375(7) . ? C6 C11 1.402(7) . ? C7 C8 1.385(8) . ? C8 C9 1.368(8) . ? C9 C10 1.394(9) . ? C10 C11 1.385(8) . ? C12 C17 1.383(8) . ? C12 C13 1.390(7) . ? C13 C14 1.397(8) . ? C14 C15 1.364(9) . ? C15 C16 1.382(9) . ? C16 C17 1.384(7) . ? C18 C19 1.380(8) . ? C18 C23 1.384(8) . ? C19 C20 1.384(7) . ? C20 C21 1.369(9) . ? C21 C22 1.383(9) . ? C22 C23 1.388(7) . ? C24 C29 1.379(8) . ? C24 C25 1.393(8) . ? C25 C26 1.387(9) . ? C26 C27 1.367(10) . ? C27 C28 1.356(10) . ? C28 C29 1.372(8) . ? 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 C5 111.0(4) . . ? O1 C1 C6 111.7(4) . . ? O1 C1 C2 106.1(4) . . ? C6 C1 C2 113.3(4) . . ? O2 C2 C12 106.3(4) . . ? O2 C2 C1 109.5(4) . . ? C12 C2 C1 109.8(4) . . ? O2 C2 C3 106.0(4) . . ? C12 C2 C3 113.7(4) . . ? C1 C2 C3 111.3(4) . . ? C4 C3 C18 110.7(4) . . ? C4 C3 C2 118.7(4) . . ? C18 C3 C2 111.5(4) . . ? O3 C4 C24 119.8(5) . . ? O3 C4 C3 121.1(5) . . ? C24 C4 C3 119.1(5) . . ? C7 C6 C11 117.6(5) . . ? C7 C6 C1 121.7(5) . . ? C11 C6 C1 120.7(5) . . ? C6 C7 C8 121.5(6) . . ? C9 C8 C7 120.4(6) . . ? C8 C9 C10 120.0(6) . . ? C11 C10 C9 118.9(6) . . ? C10 C11 C6 121.6(6) . . ? C17 C12 C13 118.7(5) . . ? C17 C12 C2 122.5(4) . . ? C13 C12 C2 118.8(5) . . ? C12 C13 C14 119.8(6) . . ? C15 C14 C13 120.7(6) . . ? C14 C15 C16 119.9(6) . . ? C15 C16 C17 119.8(6) . . ? C12 C17 C16 121.1(5) . . ? C19 C18 C23 118.3(5) . . ? C19 C18 C3 121.5(5) . . ? C23 C18 C3 120.1(5) . . ? C18 C19 C20 121.0(5) . . ? C21 C20 C19 119.8(6) . . ? C20 C21 C22 120.8(5) . . ? C21 C22 C23 118.6(6) . . ? C18 C23 C22 121.5(6) . . ? C29 C24 C25 119.0(5) . . ? C29 C24 C4 124.0(5) . . ? C25 C24 C4 117.0(5) . . ? C26 C25 C24 119.9(6) . . ? C27 C26 C25 119.7(7) . . ? C28 C27 C26 120.4(7) . . ? C27 C28 C29 121.0(7) . . ? C28 C29 C24 120.0(6) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 24.81 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.201 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.048 # Attachment 'cmpd2a.CIF' data_compound2a _database_code_depnum_ccdc_archive 'CCDC 626738' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 O3' _chemical_formula_weight 436.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)2(1)2(1) 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' _cell_length_a 6.0010(12) _cell_length_b 18.790(4) _cell_length_c 20.595(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2322.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13489 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.33 _reflns_number_total 4205 _reflns_number_gt 3448 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.3505P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(13) _refine_ls_number_reflns 4205 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.6714(2) 0.16544(8) 0.25302(7) 0.0281(4) Uani 1 1 d . . . O2 O 0.9345(2) 0.27937(9) 0.21074(7) 0.0293(4) Uani 1 1 d . . . H2 H 1.0031 0.2622 0.2427 0.035 Uiso 1 1 calc R . . O3 O 1.0147(2) 0.24843(9) 0.33417(8) 0.0341(4) Uani 1 1 d . . . C1 C 0.8116(4) 0.25021(12) 0.34319(11) 0.0268(5) Uani 1 1 d . . . C2 C 0.6682(4) 0.29997(11) 0.30143(11) 0.0231(5) Uani 1 1 d . . . H2A H 0.5090 0.2884 0.3110 0.028 Uiso 1 1 calc R . . C3 C 0.7051(4) 0.28695(12) 0.22653(11) 0.0237(5) Uani 1 1 d . . . C4 C 0.5793(4) 0.21702(11) 0.20982(10) 0.0245(5) Uani 1 1 d . . . H4 H 0.4182 0.2235 0.2208 0.029 Uiso 1 1 calc R . . C5 C 0.7130(4) 0.20843(12) 0.39733(11) 0.0277(5) Uani 1 1 d . . . C6 C 0.8461(4) 0.15606(13) 0.42581(12) 0.0349(6) Uani 1 1 d . . . H6 H 0.9905 0.1466 0.4089 0.042 Uiso 1 1 calc R . . C7 C 0.7686(5) 0.11810(14) 0.47826(13) 0.0447(7) Uani 1 1 d . . . H7 H 0.8596 0.0823 0.4972 0.054 Uiso 1 1 calc R . . C8 C 0.5591(5) 0.13155(15) 0.50368(12) 0.0472(7) Uani 1 1 d . . . H8 H 0.5077 0.1057 0.5404 0.057 Uiso 1 1 calc R . . C9 C 0.4257(5) 0.18255(14) 0.47556(12) 0.0395(6) Uani 1 1 d . . . H9 H 0.2817 0.1917 0.4928 0.047 Uiso 1 1 calc R . . C10 C 0.5005(4) 0.22059(13) 0.42226(11) 0.0310(6) Uani 1 1 d . . . H10 H 0.4066 0.2551 0.4026 0.037 Uiso 1 1 calc R . . C11 C 0.7089(4) 0.37567(11) 0.32533(10) 0.0220(5) Uani 1 1 d . . . C12 C 0.9067(4) 0.41165(12) 0.31417(11) 0.0290(6) Uani 1 1 d . . . H12 H 1.0208 0.3893 0.2896 0.035 Uiso 1 1 calc R . . C13 C 0.9411(4) 0.47942(13) 0.33808(12) 0.0338(6) Uani 1 1 d . . . H13 H 1.0774 0.5034 0.3295 0.041 Uiso 1 1 calc R . . C14 C 0.7773(4) 0.51247(13) 0.37446(12) 0.0315(6) Uani 1 1 d . . . H14 H 0.8013 0.5589 0.3914 0.038 Uiso 1 1 calc R . . C15 C 0.5794(4) 0.47773(12) 0.38595(11) 0.0307(6) Uani 1 1 d . . . H15 H 0.4660 0.5003 0.4107 0.037 Uiso 1 1 calc R . . C16 C 0.5450(4) 0.40977(12) 0.36134(11) 0.0278(5) Uani 1 1 d . . . H16 H 0.4075 0.3863 0.3693 0.033 Uiso 1 1 calc R . . C17 C 0.6145(3) 0.34742(11) 0.18580(10) 0.0229(5) Uani 1 1 d . . . C18 C 0.4019(4) 0.37423(12) 0.19648(12) 0.0285(6) Uani 1 1 d . . . H18 H 0.3123 0.3545 0.2300 0.034 Uiso 1 1 calc R . . C19 C 0.3186(4) 0.42933(12) 0.15903(12) 0.0350(6) Uani 1 1 d . . . H19 H 0.1738 0.4475 0.1675 0.042 Uiso 1 1 calc R . . C20 C 0.4442(5) 0.45785(13) 0.10964(13) 0.0422(7) Uani 1 1 d . . . H20 H 0.3871 0.4957 0.0840 0.051 Uiso 1 1 calc R . . C21 C 0.6543(4) 0.43095(14) 0.09775(13) 0.0422(7) Uani 1 1 d . . . H21 H 0.7417 0.4501 0.0635 0.051 Uiso 1 1 calc R . . C22 C 0.7383(4) 0.37618(13) 0.13542(11) 0.0333(6) Uani 1 1 d . . . H22 H 0.8830 0.3580 0.1266 0.040 Uiso 1 1 calc R . . C23 C 0.5969(4) 0.19497(11) 0.13924(11) 0.0232(5) Uani 1 1 d . . . C24 C 0.7854(4) 0.16054(12) 0.11545(11) 0.0267(5) Uani 1 1 d . . . H24 H 0.9067 0.1510 0.1438 0.032 Uiso 1 1 calc R . . C25 C 0.7983(4) 0.14016(13) 0.05126(11) 0.0320(6) Uani 1 1 d . . . H25 H 0.9279 0.1167 0.0357 0.038 Uiso 1 1 calc R . . C26 C 0.6220(4) 0.15382(13) 0.00933(12) 0.0315(6) Uani 1 1 d . . . H26 H 0.6308 0.1397 -0.0349 0.038 Uiso 1 1 calc R . . C27 C 0.4350(4) 0.18776(12) 0.03200(12) 0.0324(6) Uani 1 1 d . . . H27 H 0.3146 0.1974 0.0033 0.039 Uiso 1 1 calc R . . C28 C 0.4212(4) 0.20809(12) 0.09682(11) 0.0277(5) Uani 1 1 d . . . H28 H 0.2906 0.2311 0.1123 0.033 Uiso 1 1 calc R . . C29 C 0.5605(4) 0.09756(13) 0.25482(12) 0.0350(6) Uani 1 1 d . . . H29A H 0.6509 0.0643 0.2812 0.042 Uiso 1 1 calc R . . H29B H 0.5531 0.0783 0.2101 0.042 Uiso 1 1 calc R . . C30 C 0.3285(5) 0.10010(15) 0.28235(14) 0.0471(7) Uani 1 1 d . . . H30A H 0.3310 0.1247 0.3243 0.071 Uiso 1 1 calc R . . H30B H 0.2730 0.0515 0.2884 0.071 Uiso 1 1 calc R . . H30C H 0.2305 0.1257 0.2523 0.071 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 0.0339(9) 0.0269(9) 0.0235(9) 0.0011(7) -0.0023(7) -0.0011(7) O2 0.0211(8) 0.0392(10) 0.0276(9) -0.0021(8) 0.0026(7) 0.0026(8) O3 0.0222(10) 0.0431(10) 0.0369(10) -0.0007(8) -0.0036(7) 0.0046(7) C1 0.0304(14) 0.0243(12) 0.0258(13) -0.0090(10) -0.0029(11) 0.0025(10) C2 0.0198(11) 0.0266(13) 0.0229(12) -0.0013(10) 0.0003(9) -0.0014(10) C3 0.0199(12) 0.0258(12) 0.0256(13) -0.0024(10) 0.0039(10) 0.0002(10) C4 0.0244(12) 0.0245(12) 0.0245(13) -0.0010(10) 0.0017(10) 0.0032(10) C5 0.0367(14) 0.0266(13) 0.0197(12) -0.0058(10) -0.0036(11) -0.0018(11) C6 0.0411(16) 0.0341(14) 0.0294(14) -0.0035(12) -0.0093(11) 0.0018(12) C7 0.065(2) 0.0364(15) 0.0327(16) 0.0021(13) -0.0156(15) 0.0024(13) C8 0.078(2) 0.0429(17) 0.0204(14) 0.0039(12) -0.0031(15) -0.0172(17) C9 0.0487(15) 0.0437(16) 0.0260(14) -0.0070(12) 0.0051(13) -0.0117(14) C10 0.0359(14) 0.0336(14) 0.0235(13) -0.0029(11) -0.0015(11) -0.0034(11) C11 0.0239(12) 0.0253(12) 0.0170(12) -0.0005(10) -0.0030(10) 0.0003(10) C12 0.0259(13) 0.0303(13) 0.0309(15) -0.0030(11) 0.0012(11) -0.0006(11) C13 0.0329(13) 0.0327(14) 0.0359(15) 0.0024(12) -0.0033(12) -0.0036(11) C14 0.0410(15) 0.0249(12) 0.0287(14) 0.0014(11) -0.0078(12) -0.0016(11) C15 0.0360(14) 0.0273(13) 0.0289(14) -0.0023(11) 0.0037(11) 0.0101(12) C16 0.0264(13) 0.0307(13) 0.0263(13) 0.0013(11) 0.0043(10) -0.0009(11) C17 0.0272(13) 0.0217(12) 0.0197(12) -0.0063(9) -0.0002(9) -0.0043(10) C18 0.0263(14) 0.0310(13) 0.0281(13) -0.0010(11) 0.0007(11) 0.0001(11) C19 0.0379(14) 0.0276(14) 0.0394(16) -0.0047(12) -0.0101(13) 0.0038(12) C20 0.0613(19) 0.0307(14) 0.0346(16) 0.0019(12) -0.0142(15) 0.0010(14) C21 0.0549(18) 0.0423(16) 0.0292(16) 0.0057(13) 0.0038(13) -0.0053(14) C22 0.0361(15) 0.0339(14) 0.0300(14) -0.0018(12) 0.0052(11) -0.0008(11) C23 0.0266(12) 0.0177(11) 0.0252(13) -0.0014(9) 0.0000(10) 0.0010(10) C24 0.0269(13) 0.0291(12) 0.0243(14) -0.0008(11) -0.0034(10) 0.0021(10) C25 0.0324(13) 0.0361(14) 0.0275(14) -0.0058(11) 0.0034(12) 0.0068(12) C26 0.0407(16) 0.0321(14) 0.0216(13) -0.0033(11) -0.0023(11) -0.0013(12) C27 0.0372(14) 0.0318(13) 0.0282(14) -0.0004(11) -0.0112(12) 0.0015(12) C28 0.0252(12) 0.0250(13) 0.0330(14) -0.0039(11) -0.0025(11) 0.0002(11) C29 0.0489(16) 0.0272(13) 0.0288(14) 0.0005(11) 0.0015(13) 0.0000(12) C30 0.0535(18) 0.0418(16) 0.0459(19) -0.0052(13) 0.0064(14) -0.0144(14) _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 C4 1.427(3) . ? O1 C29 1.439(3) . ? O2 C3 1.422(3) . ? O3 C1 1.233(3) . ? C1 C5 1.487(3) . ? C1 C2 1.534(3) . ? C2 C11 1.525(3) . ? C2 C3 1.577(3) . ? C3 C17 1.513(3) . ? C3 C4 1.554(3) . ? C4 C23 1.515(3) . ? C5 C10 1.393(3) . ? C5 C6 1.397(3) . ? C6 C7 1.376(4) . ? C7 C8 1.385(4) . ? C8 C9 1.376(4) . ? C9 C10 1.385(3) . ? C11 C12 1.385(3) . ? C11 C16 1.388(3) . ? C12 C13 1.381(3) . ? C13 C14 1.383(3) . ? C14 C15 1.376(3) . ? C15 C16 1.389(3) . ? C17 C22 1.386(3) . ? C17 C18 1.389(3) . ? C18 C19 1.384(3) . ? C19 C20 1.375(4) . ? C20 C21 1.380(4) . ? C21 C22 1.384(3) . ? C23 C28 1.391(3) . ? C23 C24 1.392(3) . ? C24 C25 1.379(3) . ? C25 C26 1.390(3) . ? C26 C27 1.373(3) . ? C27 C28 1.391(3) . ? C29 C30 1.504(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C29 116.04(17) . . ? O3 C1 C5 119.5(2) . . ? O3 C1 C2 119.1(2) . . ? C5 C1 C2 121.27(19) . . ? C11 C2 C1 107.32(17) . . ? C11 C2 C3 115.97(18) . . ? C1 C2 C3 112.03(17) . . ? O2 C3 C17 107.24(17) . . ? O2 C3 C4 109.58(18) . . ? C17 C3 C4 109.72(17) . . ? O2 C3 C2 112.02(17) . . ? C17 C3 C2 112.04(17) . . ? C4 C3 C2 106.24(17) . . ? O1 C4 C23 112.66(17) . . ? O1 C4 C3 104.36(17) . . ? C23 C4 C3 114.19(18) . . ? C10 C5 C6 119.0(2) . . ? C10 C5 C1 123.6(2) . . ? C6 C5 C1 117.3(2) . . ? C7 C6 C5 120.1(2) . . ? C6 C7 C8 120.6(3) . . ? C9 C8 C7 119.7(3) . . ? C8 C9 C10 120.3(3) . . ? C9 C10 C5 120.3(2) . . ? C12 C11 C16 118.1(2) . . ? C12 C11 C2 122.6(2) . . ? C16 C11 C2 119.31(19) . . ? C13 C12 C11 121.3(2) . . ? C12 C13 C14 120.1(2) . . ? C15 C14 C13 119.6(2) . . ? C14 C15 C16 120.1(2) . . ? C11 C16 C15 120.9(2) . . ? C22 C17 C18 118.0(2) . . ? C22 C17 C3 121.00(19) . . ? C18 C17 C3 121.0(2) . . ? C19 C18 C17 121.0(2) . . ? C20 C19 C18 120.4(2) . . ? C19 C20 C21 119.3(2) . . ? C20 C21 C22 120.4(2) . . ? C21 C22 C17 120.9(2) . . ? C28 C23 C24 118.5(2) . . ? C28 C23 C4 120.1(2) . . ? C24 C23 C4 121.4(2) . . ? C25 C24 C23 120.8(2) . . ? C24 C25 C26 120.1(2) . . ? C27 C26 C25 119.8(2) . . ? C26 C27 C28 120.2(2) . . ? C27 C28 C23 120.6(2) . . ? O1 C29 C30 114.2(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.149 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.041 # Attachment 'cmpd3a.CIF' data_compound3a _database_code_depnum_ccdc_archive 'CCDC 626739' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H30 O3' _chemical_formula_weight 450.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 20.793(4) _cell_length_b 6.1220(12) _cell_length_c 20.961(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.24(3) _cell_angle_gamma 90.00 _cell_volume 2433.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7991 _diffrn_reflns_av_R_equivalents 0.0710 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4444 _reflns_number_gt 2799 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.2656P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4444 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.28470(8) 1.1288(3) -0.07995(8) 0.0323(4) Uani 1 1 d . . . O2 O 0.24830(7) 1.1217(2) 0.02698(7) 0.0276(4) Uani 1 1 d . . . H3 H 0.2658 1.1701 0.0001 0.033 Uiso 1 1 calc R . . O3 O 0.35551(7) 0.8182(2) 0.04346(7) 0.0271(4) Uani 1 1 d . . . C1 C 0.27107(10) 0.9332(4) -0.08901(11) 0.0247(5) Uani 1 1 d . . . C2 C 0.21879(10) 0.8312(4) -0.06295(10) 0.0229(5) Uani 1 1 d . . . H2 H 0.2240 0.6691 -0.0643 0.027 Uiso 1 1 calc R . . C3 C 0.23494(10) 0.8944(4) 0.01494(11) 0.0229(5) Uani 1 1 d . . . C4 C 0.29998(10) 0.7601(4) 0.06363(10) 0.0237(5) Uani 1 1 d . . . H4 H 0.2892 0.6015 0.0531 0.028 Uiso 1 1 calc R . . C5 C 0.41953(10) 0.6916(4) 0.07533(12) 0.0304(6) Uani 1 1 d . . . H5 H 0.4354 0.6936 0.1273 0.036 Uiso 1 1 calc R . . C6 C 0.40952(14) 0.4584(4) 0.05043(17) 0.0581(8) Uani 1 1 d . . . H6A H 0.3759 0.3861 0.0653 0.087 Uiso 1 1 calc R . . H6B H 0.4549 0.3817 0.0705 0.087 Uiso 1 1 calc R . . H6C H 0.3913 0.4554 -0.0007 0.087 Uiso 1 1 calc R . . C7 C 0.47341(13) 0.8051(5) 0.05693(17) 0.0584(9) Uani 1 1 d . . . H7A H 0.4585 0.8014 0.0061 0.088 Uiso 1 1 calc R . . H7B H 0.5190 0.7311 0.0799 0.088 Uiso 1 1 calc R . . H7C H 0.4780 0.9573 0.0727 0.088 Uiso 1 1 calc R . . C8 C 0.30133(11) 0.8007(4) -0.12967(10) 0.0253(5) Uani 1 1 d . . . C9 C 0.35333(11) 0.8972(4) -0.14605(12) 0.0356(6) Uani 1 1 d . . . H9 H 0.3694 1.0402 -0.1297 0.043 Uiso 1 1 calc R . . C10 C 0.38166(13) 0.7868(5) -0.18586(13) 0.0440(7) Uani 1 1 d . . . H10 H 0.4173 0.8537 -0.1966 0.053 Uiso 1 1 calc R . . C11 C 0.35834(13) 0.5796(5) -0.21012(12) 0.0418(7) Uani 1 1 d . . . H11 H 0.3776 0.5043 -0.2379 0.050 Uiso 1 1 calc R . . C12 C 0.30719(12) 0.4818(4) -0.19414(11) 0.0364(6) Uani 1 1 d . . . H12 H 0.2911 0.3392 -0.2110 0.044 Uiso 1 1 calc R . . C13 C 0.27915(11) 0.5909(4) -0.15348(11) 0.0285(6) Uani 1 1 d . . . H13 H 0.2445 0.5215 -0.1419 0.034 Uiso 1 1 calc R . . C14 C 0.14420(10) 0.8878(4) -0.11549(10) 0.0228(5) Uani 1 1 d . . . C15 C 0.10229(11) 0.7254(4) -0.15894(11) 0.0314(6) Uani 1 1 d . . . H15 H 0.1206 0.5817 -0.1558 0.038 Uiso 1 1 calc R . . C16 C 0.03396(12) 0.7699(5) -0.20690(12) 0.0395(7) Uani 1 1 d . . . H16 H 0.0058 0.6565 -0.2359 0.047 Uiso 1 1 calc R . . C17 C 0.00688(11) 0.9787(5) -0.21250(12) 0.0369(6) Uani 1 1 d . . . H17 H -0.0397 1.0101 -0.2453 0.044 Uiso 1 1 calc R . . C18 C 0.04858(11) 1.1409(4) -0.16965(11) 0.0325(6) Uani 1 1 d . . . H18 H 0.0303 1.2847 -0.1730 0.039 Uiso 1 1 calc R . . C19 C 0.11682(11) 1.0967(4) -0.12173(11) 0.0292(6) Uani 1 1 d . . . H19 H 0.1450 1.2107 -0.0930 0.035 Uiso 1 1 calc R . . C20 C 0.17276(10) 0.8379(4) 0.03226(10) 0.0214(5) Uani 1 1 d . . . C21 C 0.14470(11) 0.6272(4) 0.02173(10) 0.0260(5) Uani 1 1 d . . . H21 H 0.1639 0.5183 0.0024 0.031 Uiso 1 1 calc R . . C22 C 0.08915(11) 0.5749(4) 0.03918(11) 0.0306(6) Uani 1 1 d . . . H22 H 0.0704 0.4309 0.0316 0.037 Uiso 1 1 calc R . . C23 C 0.06089(11) 0.7321(4) 0.06765(11) 0.0334(6) Uani 1 1 d . . . H23 H 0.0227 0.6964 0.0795 0.040 Uiso 1 1 calc R . . C24 C 0.08811(12) 0.9395(4) 0.07866(12) 0.0339(6) Uani 1 1 d . . . H24 H 0.0686 1.0475 0.0980 0.041 Uiso 1 1 calc R . . C25 C 0.14402(11) 0.9922(4) 0.06169(11) 0.0304(6) Uani 1 1 d . . . H25 H 0.1630 1.1358 0.0703 0.037 Uiso 1 1 calc R . . C26 C 0.31793(10) 0.7965(4) 0.14036(11) 0.0244(5) Uani 1 1 d . . . C27 C 0.30140(11) 0.6367(4) 0.17811(11) 0.0292(6) Uani 1 1 d . . . H27 H 0.2812 0.5029 0.1560 0.035 Uiso 1 1 calc R . . C28 C 0.31394(11) 0.6696(4) 0.24788(12) 0.0356(6) Uani 1 1 d . . . H28 H 0.3023 0.5591 0.2732 0.043 Uiso 1 1 calc R . . C29 C 0.34321(11) 0.8628(4) 0.27998(12) 0.0360(6) Uani 1 1 d . . . H29 H 0.3513 0.8866 0.3275 0.043 Uiso 1 1 calc R . . C30 C 0.36092(12) 1.0229(4) 0.24353(12) 0.0344(6) Uani 1 1 d . . . H30 H 0.3813 1.1561 0.2660 0.041 Uiso 1 1 calc R . . C31 C 0.34895(11) 0.9892(4) 0.17408(11) 0.0296(6) Uani 1 1 d . . . H31 H 0.3620 1.0984 0.1494 0.036 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 0.0409(9) 0.0233(10) 0.0362(9) 0.0004(8) 0.0194(7) -0.0048(8) O2 0.0340(9) 0.0228(9) 0.0282(9) -0.0030(7) 0.0150(7) -0.0046(7) O3 0.0244(8) 0.0303(10) 0.0271(8) 0.0020(7) 0.0111(6) -0.0002(7) C1 0.0241(11) 0.0262(15) 0.0200(11) 0.0030(10) 0.0051(9) 0.0000(11) C2 0.0262(11) 0.0210(13) 0.0223(11) -0.0027(10) 0.0109(9) -0.0016(10) C3 0.0267(11) 0.0187(13) 0.0239(12) -0.0041(10) 0.0111(9) -0.0036(10) C4 0.0235(11) 0.0249(13) 0.0260(12) 0.0006(10) 0.0135(9) -0.0026(10) C5 0.0201(11) 0.0375(16) 0.0308(13) -0.0004(12) 0.0075(9) 0.0028(11) C6 0.0373(15) 0.0381(18) 0.095(2) -0.0056(17) 0.0236(15) 0.0044(14) C7 0.0319(14) 0.050(2) 0.095(2) 0.0065(17) 0.0286(15) -0.0044(13) C8 0.0231(11) 0.0316(15) 0.0207(11) 0.0028(11) 0.0084(9) 0.0026(11) C9 0.0345(13) 0.0378(16) 0.0376(14) -0.0012(12) 0.0181(11) -0.0054(12) C10 0.0430(15) 0.055(2) 0.0440(15) -0.0041(15) 0.0285(12) -0.0050(14) C11 0.0478(15) 0.051(2) 0.0351(15) -0.0029(13) 0.0254(12) 0.0051(14) C12 0.0478(15) 0.0343(15) 0.0282(13) -0.0002(12) 0.0165(11) 0.0047(13) C13 0.0353(13) 0.0271(15) 0.0257(12) 0.0019(11) 0.0151(10) 0.0010(11) C14 0.0241(11) 0.0275(14) 0.0205(11) 0.0027(10) 0.0130(9) -0.0024(11) C15 0.0307(12) 0.0275(14) 0.0334(13) 0.0029(12) 0.0105(10) -0.0019(11) C16 0.0315(13) 0.0424(17) 0.0359(14) 0.0005(13) 0.0049(11) -0.0113(13) C17 0.0229(12) 0.0507(18) 0.0341(14) 0.0058(14) 0.0088(10) 0.0008(13) C18 0.0306(13) 0.0360(15) 0.0330(13) 0.0037(12) 0.0151(11) 0.0078(12) C19 0.0310(12) 0.0301(15) 0.0267(12) -0.0024(11) 0.0122(10) -0.0001(11) C20 0.0253(11) 0.0231(13) 0.0140(10) -0.0006(10) 0.0061(9) 0.0013(10) C21 0.0279(12) 0.0292(14) 0.0211(11) -0.0023(11) 0.0101(9) 0.0006(11) C22 0.0312(12) 0.0341(15) 0.0252(12) -0.0012(11) 0.0103(10) -0.0046(11) C23 0.0282(12) 0.0509(18) 0.0246(12) -0.0003(12) 0.0143(10) -0.0058(13) C24 0.0330(13) 0.0423(17) 0.0303(13) -0.0051(12) 0.0169(10) 0.0035(12) C25 0.0346(13) 0.0275(14) 0.0282(13) -0.0008(11) 0.0119(10) 0.0010(11) C26 0.0196(11) 0.0280(14) 0.0239(12) 0.0002(11) 0.0071(9) 0.0014(10) C27 0.0275(12) 0.0318(14) 0.0263(13) 0.0019(11) 0.0091(9) -0.0020(11) C28 0.0290(12) 0.0492(18) 0.0286(13) 0.0075(13) 0.0119(10) -0.0010(12) C29 0.0325(13) 0.0525(18) 0.0220(12) -0.0028(13) 0.0104(10) 0.0051(13) C30 0.0354(13) 0.0357(16) 0.0272(13) -0.0065(12) 0.0079(10) -0.0006(12) C31 0.0271(12) 0.0309(15) 0.0286(13) 0.0008(12) 0.0093(10) -0.0016(11) _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 1.227(3) . ? O2 C3 1.421(3) . ? O3 C4 1.428(2) . ? O3 C5 1.445(3) . ? C1 C8 1.490(3) . ? C1 C2 1.535(3) . ? C2 C14 1.528(3) . ? C2 C3 1.574(3) . ? C3 C20 1.519(3) . ? C3 C4 1.554(3) . ? C4 C26 1.511(3) . ? C5 C7 1.497(3) . ? C5 C6 1.505(3) . ? C8 C13 1.386(3) . ? C8 C9 1.393(3) . ? C9 C10 1.380(3) . ? C10 C11 1.378(4) . ? C11 C12 1.376(3) . ? C12 C13 1.386(3) . ? C14 C19 1.385(3) . ? C14 C15 1.388(3) . ? C15 C16 1.389(3) . ? C16 C17 1.382(4) . ? C17 C18 1.380(3) . ? C18 C19 1.387(3) . ? C20 C25 1.390(3) . ? C20 C21 1.396(3) . ? C21 C22 1.385(3) . ? C22 C23 1.384(3) . ? C23 C24 1.370(3) . ? C24 C25 1.386(3) . ? C26 C27 1.387(3) . ? C26 C31 1.391(3) . ? C27 C28 1.391(3) . ? C28 C29 1.373(3) . ? C29 C30 1.382(3) . ? C30 C31 1.388(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O3 C5 115.64(16) . . ? O1 C1 C8 119.7(2) . . ? O1 C1 C2 119.6(2) . . ? C8 C1 C2 120.59(19) . . ? C14 C2 C1 107.99(16) . . ? C14 C2 C3 114.39(17) . . ? C1 C2 C3 112.86(16) . . ? O2 C3 C20 107.67(17) . . ? O2 C3 C4 110.34(16) . . ? C20 C3 C4 108.63(17) . . ? O2 C3 C2 111.57(17) . . ? C20 C3 C2 110.61(16) . . ? C4 C3 C2 107.99(17) . . ? O3 C4 C26 113.70(16) . . ? O3 C4 C3 105.38(16) . . ? C26 C4 C3 112.91(17) . . ? O3 C5 C7 106.04(19) . . ? O3 C5 C6 112.25(18) . . ? C7 C5 C6 111.3(2) . . ? C13 C8 C9 118.8(2) . . ? C13 C8 C1 123.6(2) . . ? C9 C8 C1 117.6(2) . . ? C10 C9 C8 120.6(2) . . ? C11 C10 C9 120.1(2) . . ? C12 C11 C10 120.0(2) . . ? C11 C12 C13 120.2(2) . . ? C12 C13 C8 120.4(2) . . ? C19 C14 C15 118.5(2) . . ? C19 C14 C2 122.25(19) . . ? C15 C14 C2 119.3(2) . . ? C14 C15 C16 121.0(2) . . ? C17 C16 C15 120.2(2) . . ? C18 C17 C16 119.0(2) . . ? C17 C18 C19 120.9(2) . . ? C14 C19 C18 120.5(2) . . ? C25 C20 C21 118.1(2) . . ? C25 C20 C3 121.0(2) . . ? C21 C20 C3 120.92(19) . . ? C22 C21 C20 120.8(2) . . ? C23 C22 C21 120.0(2) . . ? C24 C23 C22 119.8(2) . . ? C23 C24 C25 120.3(2) . . ? C24 C25 C20 120.9(2) . . ? C27 C26 C31 118.7(2) . . ? C27 C26 C4 119.5(2) . . ? C31 C26 C4 121.8(2) . . ? C26 C27 C28 120.9(2) . . ? C29 C28 C27 119.6(2) . . ? C28 C29 C30 120.3(2) . . ? C29 C30 C31 120.0(2) . . ? C30 C31 C26 120.3(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.187 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.051 # Attachment 'cmpd10.CIF' data_compound10 _database_code_depnum_ccdc_archive 'CCDC 626740' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 O' _chemical_formula_weight 286.35 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 5.7983(12) _cell_length_b 9.0444(18) _cell_length_c 15.820(3) _cell_angle_alpha 94.69(3) _cell_angle_beta 100.00(3) _cell_angle_gamma 106.81(3) _cell_volume 774.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4993 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2689 _reflns_number_gt 1927 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.2482P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2689 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.3415(3) 0.37865(19) 0.15478(11) 0.0502(5) Uani 1 1 d . . . C1 C 0.1863(4) 0.4442(3) 0.16040(15) 0.0371(5) Uani 1 1 d . . . C2 C -0.0036(4) 0.3930(2) 0.21647(14) 0.0354(5) Uani 1 1 d . . . H2 H -0.1641 0.3969 0.1829 0.043 Uiso 1 1 calc R . . C3 C 0.1838(4) 0.5819(2) 0.11334(14) 0.0330(5) Uani 1 1 d . . . C4 C 0.3515(4) 0.6234(3) 0.05964(14) 0.0378(6) Uani 1 1 d . . . H4 H 0.4641 0.5664 0.0549 0.045 Uiso 1 1 calc R . . C5 C 0.3562(4) 0.7474(3) 0.01281(15) 0.0435(6) Uani 1 1 d . . . H5 H 0.4688 0.7734 -0.0247 0.052 Uiso 1 1 calc R . . C6 C 0.1974(4) 0.8321(3) 0.02104(15) 0.0455(6) Uani 1 1 d . . . H6 H 0.2002 0.9168 -0.0110 0.055 Uiso 1 1 calc R . . C7 C 0.0332(4) 0.7947(3) 0.07571(16) 0.0458(6) Uani 1 1 d . . . H7 H -0.0734 0.8553 0.0822 0.055 Uiso 1 1 calc R . . C8 C 0.0242(4) 0.6693(3) 0.12079(14) 0.0383(6) Uani 1 1 d . . . H8 H -0.0916 0.6425 0.1571 0.046 Uiso 1 1 calc R . . C9 C -0.0447(4) 0.2267(2) 0.23702(14) 0.0345(5) Uani 1 1 d . . . C10 C 0.1444(4) 0.1800(3) 0.28198(16) 0.0446(6) Uani 1 1 d . . . H10 H 0.3058 0.2518 0.2989 0.053 Uiso 1 1 calc R . . C11 C 0.0993(5) 0.0298(3) 0.30224(17) 0.0466(6) Uani 1 1 d . . . H11 H 0.2303 -0.0012 0.3324 0.056 Uiso 1 1 calc R . . C12 C -0.1348(5) -0.0754(3) 0.27891(16) 0.0448(6) Uani 1 1 d . . . H12 H -0.1653 -0.1782 0.2935 0.054 Uiso 1 1 calc R . . C13 C -0.3237(5) -0.0307(3) 0.23451(15) 0.0432(6) Uani 1 1 d . . . H13 H -0.4852 -0.1026 0.2185 0.052 Uiso 1 1 calc R . . C14 C -0.2780(4) 0.1195(3) 0.21317(14) 0.0374(6) Uani 1 1 d . . . H14 H -0.4088 0.1492 0.1817 0.045 Uiso 1 1 calc R . . C15 C 0.0615(4) 0.5092(2) 0.29938(14) 0.0334(5) Uani 1 1 d . . . C16 C 0.2946(4) 0.6119(3) 0.33199(16) 0.0416(6) Uani 1 1 d . . . H16 H 0.4231 0.6126 0.3019 0.050 Uiso 1 1 calc R . . C17 C 0.3443(4) 0.7139(3) 0.40773(17) 0.0461(6) Uani 1 1 d . . . H17 H 0.5059 0.7840 0.4283 0.055 Uiso 1 1 calc R . . C18 C 0.1635(5) 0.7159(3) 0.45424(15) 0.0419(6) Uani 1 1 d . . . C19 C -0.0686(5) 0.6113(3) 0.42204(17) 0.0460(6) Uani 1 1 d . . . H19 H -0.1957 0.6086 0.4531 0.055 Uiso 1 1 calc R . . C20 C -0.1201(4) 0.5107(3) 0.34597(16) 0.0409(6) Uani 1 1 d . . . H20 H -0.2823 0.4414 0.3252 0.049 Uiso 1 1 calc R . . C21 C 0.2155(6) 0.8284(3) 0.53469(18) 0.0635(8) Uani 1 1 d . . . H21A H 0.1668 0.9199 0.5204 0.095 Uiso 1 1 calc R . . H21B H 0.3919 0.8609 0.5604 0.095 Uiso 1 1 calc R . . H21C H 0.1219 0.7782 0.5761 0.095 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 0.0464(10) 0.0587(11) 0.0585(12) 0.0171(9) 0.0229(9) 0.0267(9) C1 0.0314(12) 0.0426(13) 0.0358(13) 0.0029(10) 0.0057(10) 0.0106(11) C2 0.0247(11) 0.0425(13) 0.0368(13) 0.0051(10) 0.0047(10) 0.0079(10) C3 0.0286(12) 0.0365(12) 0.0288(12) 0.0024(9) 0.0015(10) 0.0053(10) C4 0.0356(13) 0.0425(13) 0.0313(13) -0.0013(10) 0.0072(10) 0.0077(10) C5 0.0385(14) 0.0530(15) 0.0328(13) 0.0057(11) 0.0095(11) 0.0038(12) C6 0.0457(15) 0.0458(14) 0.0393(14) 0.0154(11) 0.0045(12) 0.0051(12) C7 0.0413(14) 0.0498(15) 0.0502(15) 0.0137(12) 0.0084(12) 0.0185(12) C8 0.0320(12) 0.0486(14) 0.0363(13) 0.0126(11) 0.0100(10) 0.0120(11) C9 0.0319(12) 0.0381(12) 0.0330(12) 0.0063(10) 0.0088(10) 0.0082(10) C10 0.0290(13) 0.0490(15) 0.0529(16) 0.0120(12) 0.0052(11) 0.0084(11) C11 0.0425(15) 0.0493(15) 0.0538(16) 0.0163(12) 0.0114(12) 0.0194(12) C12 0.0504(16) 0.0376(13) 0.0477(15) 0.0054(11) 0.0175(12) 0.0114(12) C13 0.0419(14) 0.0382(13) 0.0409(14) -0.0004(11) 0.0098(11) 0.0003(11) C14 0.0297(12) 0.0468(14) 0.0314(13) 0.0023(10) 0.0050(10) 0.0067(11) C15 0.0261(12) 0.0366(12) 0.0395(13) 0.0106(10) 0.0078(10) 0.0107(10) C16 0.0337(13) 0.0461(14) 0.0447(15) 0.0021(11) 0.0111(11) 0.0114(11) C17 0.0350(14) 0.0430(14) 0.0536(16) 0.0039(12) 0.0043(12) 0.0051(11) C18 0.0511(15) 0.0377(13) 0.0402(14) 0.0081(11) 0.0113(12) 0.0170(12) C19 0.0442(15) 0.0492(15) 0.0520(16) 0.0126(12) 0.0204(12) 0.0183(12) C20 0.0330(13) 0.0408(13) 0.0479(15) 0.0072(11) 0.0115(11) 0.0078(10) C21 0.080(2) 0.0593(17) 0.0478(17) -0.0012(13) 0.0130(15) 0.0192(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.224(3) . ? C1 C3 1.505(3) . ? C1 C2 1.525(3) . ? C2 C9 1.524(3) . ? C2 C15 1.530(3) . ? C3 C4 1.392(3) . ? C3 C8 1.393(3) . ? C4 C5 1.390(3) . ? C5 C6 1.373(3) . ? C6 C7 1.384(3) . ? C7 C8 1.382(3) . ? C9 C14 1.384(3) . ? C9 C10 1.391(3) . ? C10 C11 1.383(3) . ? C11 C12 1.381(3) . ? C12 C13 1.375(3) . ? C13 C14 1.389(3) . ? C15 C16 1.382(3) . ? C15 C20 1.389(3) . ? C16 C17 1.384(3) . ? C17 C18 1.385(3) . ? C18 C19 1.383(3) . ? C18 C21 1.491(3) . ? C19 C20 1.380(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 120.1(2) . . ? O1 C1 C2 121.7(2) . . ? C3 C1 C2 118.25(18) . . ? C9 C2 C1 114.32(18) . . ? C9 C2 C15 111.14(18) . . ? C1 C2 C15 110.36(18) . . ? C4 C3 C8 118.7(2) . . ? C4 C3 C1 117.62(19) . . ? C8 C3 C1 123.7(2) . . ? C5 C4 C3 120.7(2) . . ? C6 C5 C4 119.7(2) . . ? C5 C6 C7 120.3(2) . . ? C8 C7 C6 120.1(2) . . ? C7 C8 C3 120.4(2) . . ? C14 C9 C10 118.5(2) . . ? C14 C9 C2 119.6(2) . . ? C10 C9 C2 121.9(2) . . ? C11 C10 C9 120.5(2) . . ? C12 C11 C10 120.4(2) . . ? C13 C12 C11 119.7(2) . . ? C12 C13 C14 119.9(2) . . ? C9 C14 C13 121.0(2) . . ? C16 C15 C20 117.6(2) . . ? C16 C15 C2 123.47(19) . . ? C20 C15 C2 118.94(19) . . ? C15 C16 C17 121.2(2) . . ? C16 C17 C18 121.4(2) . . ? C19 C18 C17 117.2(2) . . ? C19 C18 C21 121.4(2) . . ? C17 C18 C21 121.4(2) . . ? C20 C19 C18 121.7(2) . . ? C19 C20 C15 121.0(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.216 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.044 # Attachment 'cmpd13.CIF' data_compound13 _database_code_depnum_ccdc_archive 'CCDC 626741' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H20 Ga3 I5 O4' _chemical_formula_weight 1264.10 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0898(18) _cell_length_b 19.066(4) _cell_length_c 20.516(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.84(3) _cell_angle_gamma 90.00 _cell_volume 3537.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2312 _exptl_absorpt_coefficient_mu 6.663 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.538 _exptl_absorpt_correction_T_max 0.776 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15044 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7690 _reflns_number_gt 5803 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+3.1850P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7690 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 I1 I 0.43065(5) 0.15638(2) 0.14667(2) 0.03841(12) Uani 1 1 d . . . Ga1 Ga 0.19876(7) 0.21314(3) 0.10473(3) 0.02126(14) Uani 1 1 d . . . O1 O 0.2241(4) 0.27717(18) 0.03043(16) 0.0232(8) Uani 1 1 d . . . C1 C 0.2365(6) 0.3475(3) 0.0509(2) 0.0210(11) Uani 1 1 d . . . I2 I 0.11870(6) 0.27428(3) 0.31601(2) 0.04762(14) Uani 1 1 d . . . Ga2 Ga 0.01165(7) 0.27641(3) 0.20087(3) 0.02320(14) Uani 1 1 d . . . O2 O 0.1636(4) 0.30138(19) 0.14717(17) 0.0244(8) Uani 1 1 d . . . C2 C 0.2058(6) 0.3606(3) 0.1128(3) 0.0227(12) Uani 1 1 d . . . I3 I -0.23600(5) 0.32639(2) 0.16886(2) 0.03694(12) Uani 1 1 d . . . Ga3 Ga 0.06439(7) 0.24498(3) -0.03155(3) 0.02398(15) Uani 1 1 d . . . O3 O 0.0630(4) 0.17373(19) 0.03592(16) 0.0224(8) Uani 1 1 d . . . C3 C 0.2928(6) 0.3951(3) 0.0029(2) 0.0246(12) Uani 1 1 d . . . I4 I 0.15265(6) 0.20257(3) -0.13402(2) 0.04796(14) Uani 1 1 d . . . O4 O 0.0392(4) 0.18607(18) 0.16002(16) 0.0207(8) Uani 1 1 d . . . C4 C 0.2397(8) 0.4630(3) -0.0077(3) 0.0352(15) Uani 1 1 d . . . H4 H 0.1633 0.4802 0.0163 0.042 Uiso 1 1 calc R . . I5 I -0.15016(5) 0.32424(2) -0.03075(2) 0.04216(13) Uani 1 1 d . . . C5 C 0.2981(9) 0.5055(3) -0.0533(3) 0.0451(19) Uani 1 1 d . . . H5 H 0.2620 0.5519 -0.0600 0.054 Uiso 1 1 calc R . . C6 C 0.4074(8) 0.4813(4) -0.0887(3) 0.0398(16) Uani 1 1 d . . . H6 H 0.4463 0.5110 -0.1200 0.048 Uiso 1 1 calc R . . C7 C 0.4613(7) 0.4141(4) -0.0792(3) 0.0402(16) Uani 1 1 d . . . H7 H 0.5376 0.3976 -0.1037 0.048 Uiso 1 1 calc R . . C8 C 0.4044(7) 0.3709(3) -0.0341(3) 0.0351(15) Uani 1 1 d . . . H8 H 0.4408 0.3244 -0.0280 0.042 Uiso 1 1 calc R . . C9 C 0.2325(6) 0.4246(3) 0.1531(3) 0.0238(12) Uani 1 1 d . . . C10 C 0.1410(7) 0.4828(3) 0.1452(3) 0.0342(15) Uani 1 1 d . . . H10 H 0.0571 0.4826 0.1136 0.041 Uiso 1 1 calc R . . C11 C 0.1743(9) 0.5420(3) 0.1846(3) 0.0447(19) Uani 1 1 d . . . H11 H 0.1106 0.5816 0.1809 0.054 Uiso 1 1 calc R . . C12 C 0.2985(9) 0.5428(4) 0.2285(3) 0.0473(19) Uani 1 1 d . . . H12 H 0.3232 0.5840 0.2533 0.057 Uiso 1 1 calc R . . C13 C 0.3880(8) 0.4843(4) 0.2370(3) 0.0496(19) Uani 1 1 d . . . H13 H 0.4724 0.4848 0.2684 0.060 Uiso 1 1 calc R . . C14 C 0.3545(7) 0.4250(4) 0.1999(3) 0.0389(16) Uani 1 1 d . . . H14 H 0.4149 0.3844 0.2063 0.047 Uiso 1 1 calc R . . C15 C -0.0599(6) 0.1401(3) 0.0591(3) 0.0241(12) Uani 1 1 d . . . C16 C -0.0671(6) 0.1432(3) 0.1251(3) 0.0227(12) Uani 1 1 d . . . C17 C -0.1597(6) 0.1056(3) 0.0083(2) 0.0248(12) Uani 1 1 d . . . C18 C -0.1014(7) 0.0658(3) -0.0403(3) 0.0324(14) Uani 1 1 d . . . H18 H 0.0027 0.0618 -0.0408 0.039 Uiso 1 1 calc R . . C19 C -0.1960(9) 0.0324(4) -0.0876(3) 0.0447(17) Uani 1 1 d . . . H19 H -0.1564 0.0043 -0.1198 0.054 Uiso 1 1 calc R . . C20 C -0.3449(9) 0.0395(4) -0.0886(3) 0.0486(19) Uani 1 1 d . . . H20 H -0.4085 0.0164 -0.1214 0.058 Uiso 1 1 calc R . . C21 C -0.4051(8) 0.0808(4) -0.0414(3) 0.0466(18) Uani 1 1 d . . . H21 H -0.5092 0.0858 -0.0422 0.056 Uiso 1 1 calc R . . C22 C -0.3116(7) 0.1141(3) 0.0064(3) 0.0343(14) Uani 1 1 d . . . H22 H -0.3517 0.1429 0.0380 0.041 Uiso 1 1 calc R . . C23 C -0.1590(6) 0.1009(3) 0.1647(2) 0.0208(11) Uani 1 1 d . . . C24 C -0.2095(6) 0.0344(3) 0.1440(3) 0.0255(12) Uani 1 1 d . . . H24 H -0.1875 0.0172 0.1027 0.031 Uiso 1 1 calc R . . C25 C -0.2910(7) -0.0069(3) 0.1826(3) 0.0326(14) Uani 1 1 d . . . H25 H -0.3244 -0.0519 0.1677 0.039 Uiso 1 1 calc R . . C26 C -0.3238(7) 0.0176(3) 0.2435(3) 0.0337(14) Uani 1 1 d . . . H26 H -0.3799 -0.0104 0.2701 0.040 Uiso 1 1 calc R . . C27 C -0.2743(7) 0.0829(3) 0.2648(3) 0.0299(14) Uani 1 1 d . . . H27 H -0.2973 0.1001 0.3061 0.036 Uiso 1 1 calc R . . C28 C -0.1911(6) 0.1236(3) 0.2260(3) 0.0254(12) Uani 1 1 d . . . H28 H -0.1553 0.1679 0.2418 0.030 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 I1 0.0250(2) 0.0436(3) 0.0462(3) 0.0106(2) 0.00145(18) 0.00810(18) Ga1 0.0218(3) 0.0191(3) 0.0229(3) 0.0009(2) 0.0021(2) 0.0000(2) O1 0.030(2) 0.019(2) 0.0201(19) -0.0009(15) 0.0032(16) -0.0013(16) C1 0.023(3) 0.019(3) 0.020(3) -0.001(2) -0.004(2) 0.001(2) I2 0.0531(3) 0.0663(3) 0.0221(2) -0.0029(2) -0.00300(19) -0.0149(2) Ga2 0.0275(4) 0.0224(3) 0.0200(3) -0.0014(2) 0.0039(2) -0.0016(3) O2 0.029(2) 0.021(2) 0.024(2) -0.0035(16) 0.0074(16) -0.0013(17) C2 0.023(3) 0.016(3) 0.030(3) -0.001(2) 0.004(2) -0.005(2) I3 0.0356(3) 0.0343(2) 0.0418(2) 0.00851(18) 0.00775(19) 0.01054(18) Ga3 0.0312(4) 0.0224(3) 0.0184(3) -0.0016(2) 0.0031(3) -0.0001(3) O3 0.025(2) 0.023(2) 0.0194(18) 0.0015(16) 0.0023(15) -0.0035(16) C3 0.030(3) 0.026(3) 0.017(3) -0.001(2) 0.000(2) -0.007(2) I4 0.0667(4) 0.0502(3) 0.0304(2) -0.0130(2) 0.0215(2) -0.0064(2) O4 0.022(2) 0.0172(19) 0.0226(19) -0.0015(15) 0.0030(15) -0.0018(16) C4 0.057(4) 0.021(3) 0.029(3) 0.001(3) 0.009(3) 0.005(3) I5 0.0429(3) 0.0424(3) 0.0388(2) -0.0056(2) -0.00760(19) 0.0170(2) C5 0.087(6) 0.019(3) 0.030(3) 0.004(3) 0.010(4) -0.006(3) C6 0.056(5) 0.039(4) 0.023(3) 0.011(3) -0.001(3) -0.018(3) C7 0.029(4) 0.056(5) 0.036(4) 0.010(3) 0.004(3) 0.000(3) C8 0.042(4) 0.029(3) 0.034(3) 0.009(3) 0.004(3) 0.001(3) C9 0.024(3) 0.026(3) 0.023(3) -0.002(2) 0.005(2) -0.007(2) C10 0.047(4) 0.028(3) 0.028(3) -0.004(3) 0.004(3) 0.004(3) C11 0.080(6) 0.024(3) 0.034(4) -0.003(3) 0.026(4) 0.000(3) C12 0.057(5) 0.048(4) 0.040(4) -0.020(3) 0.021(4) -0.025(4) C13 0.040(4) 0.070(5) 0.038(4) -0.021(4) 0.004(3) -0.017(4) C14 0.035(4) 0.049(4) 0.032(3) -0.012(3) 0.002(3) -0.005(3) C15 0.022(3) 0.020(3) 0.031(3) -0.003(2) 0.000(2) 0.000(2) C16 0.025(3) 0.017(3) 0.026(3) -0.002(2) -0.003(2) -0.001(2) C17 0.031(3) 0.025(3) 0.018(3) 0.002(2) -0.001(2) 0.000(2) C18 0.034(4) 0.033(3) 0.030(3) -0.008(3) -0.001(3) -0.004(3) C19 0.058(5) 0.038(4) 0.036(4) -0.012(3) -0.007(3) 0.000(3) C20 0.057(5) 0.047(4) 0.036(4) -0.001(3) -0.022(3) -0.015(4) C21 0.029(4) 0.058(5) 0.049(4) 0.005(4) -0.010(3) -0.009(3) C22 0.027(3) 0.038(4) 0.038(3) 0.001(3) 0.002(3) -0.007(3) C23 0.015(3) 0.023(3) 0.024(3) 0.002(2) -0.002(2) 0.002(2) C24 0.028(3) 0.021(3) 0.028(3) 0.003(2) 0.001(2) 0.006(2) C25 0.037(4) 0.017(3) 0.043(4) 0.009(3) 0.000(3) 0.000(3) C26 0.034(4) 0.030(3) 0.039(3) 0.011(3) 0.010(3) -0.003(3) C27 0.031(4) 0.033(3) 0.026(3) 0.006(3) 0.006(3) 0.003(3) C28 0.024(3) 0.027(3) 0.025(3) 0.008(2) 0.000(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Ga1 2.4465(9) . ? Ga1 O3 1.930(4) . ? Ga1 O2 1.936(4) . ? Ga1 O1 1.984(3) . ? Ga1 O4 1.998(3) . ? O1 C1 1.406(6) . ? O1 Ga3 1.930(4) . ? C1 C2 1.350(7) . ? C1 C3 1.470(7) . ? I2 Ga2 2.4618(10) . ? Ga2 O2 1.913(4) . ? Ga2 O4 1.943(3) . ? Ga2 I3 2.4710(9) . ? O2 C2 1.405(6) . ? C2 C9 1.480(7) . ? Ga3 O3 1.940(3) . ? Ga3 I4 2.4617(8) . ? Ga3 I5 2.4686(8) . ? O3 C15 1.412(6) . ? C3 C4 1.391(8) . ? C3 C8 1.405(8) . ? O4 C16 1.406(6) . ? C4 C5 1.382(8) . ? C5 C6 1.369(9) . ? C6 C7 1.380(9) . ? C7 C8 1.377(8) . ? C9 C10 1.386(8) . ? C9 C14 1.392(8) . ? C10 C11 1.402(8) . ? C11 C12 1.370(10) . ? C12 C13 1.382(10) . ? C13 C14 1.379(9) . ? C15 C16 1.363(7) . ? C15 C17 1.466(8) . ? C16 C23 1.465(7) . ? C17 C22 1.387(8) . ? C17 C18 1.400(8) . ? C18 C19 1.385(8) . ? C19 C20 1.358(10) . ? C20 C21 1.401(10) . ? C21 C22 1.385(9) . ? C23 C28 1.390(7) . ? C23 C24 1.399(8) . ? C24 C25 1.383(8) . ? C25 C26 1.394(8) . ? C26 C27 1.379(8) . ? C27 C28 1.389(7) . ? 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 O3 Ga1 O2 123.00(16) . . ? O3 Ga1 O1 78.07(15) . . ? O2 Ga1 O1 81.27(15) . . ? O3 Ga1 O4 82.40(14) . . ? O2 Ga1 O4 78.84(14) . . ? O1 Ga1 O4 137.98(15) . . ? O3 Ga1 I1 123.29(11) . . ? O2 Ga1 I1 113.71(12) . . ? O1 Ga1 I1 112.27(11) . . ? O4 Ga1 I1 109.59(11) . . ? C1 O1 Ga3 122.2(3) . . ? C1 O1 Ga1 111.6(3) . . ? Ga3 O1 Ga1 99.90(16) . . ? C2 C1 O1 116.1(4) . . ? C2 C1 C3 129.5(5) . . ? O1 C1 C3 114.3(4) . . ? O2 Ga2 O4 80.78(15) . . ? O2 Ga2 I2 108.59(12) . . ? O4 Ga2 I2 110.09(11) . . ? O2 Ga2 I3 116.27(12) . . ? O4 Ga2 I3 112.41(11) . . ? I2 Ga2 I3 121.45(4) . . ? C2 O2 Ga2 137.7(3) . . ? C2 O2 Ga1 114.0(3) . . ? Ga2 O2 Ga1 101.82(17) . . ? C1 C2 O2 114.6(4) . . ? C1 C2 C9 129.7(5) . . ? O2 C2 C9 114.8(4) . . ? O1 Ga3 O3 79.15(15) . . ? O1 Ga3 I4 112.23(11) . . ? O3 Ga3 I4 113.93(11) . . ? O1 Ga3 I5 110.05(11) . . ? O3 Ga3 I5 111.18(11) . . ? I4 Ga3 I5 122.21(4) . . ? C15 O3 Ga1 113.5(3) . . ? C15 O3 Ga3 128.4(3) . . ? Ga1 O3 Ga3 101.48(17) . . ? C4 C3 C8 118.6(5) . . ? C4 C3 C1 122.7(5) . . ? C8 C3 C1 118.6(5) . . ? C16 O4 Ga2 128.6(3) . . ? C16 O4 Ga1 111.2(3) . . ? Ga2 O4 Ga1 98.57(15) . . ? C5 C4 C3 120.0(6) . . ? C6 C5 C4 120.8(6) . . ? C5 C6 C7 120.3(6) . . ? C8 C7 C6 119.9(6) . . ? C7 C8 C3 120.5(6) . . ? C10 C9 C14 120.2(6) . . ? C10 C9 C2 122.2(5) . . ? C14 C9 C2 117.6(5) . . ? C9 C10 C11 119.0(6) . . ? C12 C11 C10 120.2(7) . . ? C11 C12 C13 120.5(6) . . ? C14 C13 C12 119.9(7) . . ? C13 C14 C9 120.1(7) . . ? C16 C15 O3 115.7(5) . . ? C16 C15 C17 129.6(5) . . ? O3 C15 C17 114.7(4) . . ? C15 C16 O4 115.6(5) . . ? C15 C16 C23 127.9(5) . . ? O4 C16 C23 116.0(4) . . ? C22 C17 C18 119.4(5) . . ? C22 C17 C15 120.7(5) . . ? C18 C17 C15 119.9(5) . . ? C19 C18 C17 119.7(6) . . ? C20 C19 C18 120.7(6) . . ? C19 C20 C21 120.3(6) . . ? C22 C21 C20 119.5(7) . . ? C21 C22 C17 120.3(6) . . ? C28 C23 C24 117.6(5) . . ? C28 C23 C16 121.0(5) . . ? C24 C23 C16 121.2(5) . . ? C25 C24 C23 121.4(5) . . ? C24 C25 C26 119.8(5) . . ? C27 C26 C25 119.7(5) . . ? C26 C27 C28 120.1(5) . . ? C27 C28 C23 121.5(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.152 _refine_diff_density_min -1.165 _refine_diff_density_rms 0.169 # Attachment 'cmpd14.CIF' data_compound14 _database_code_depnum_ccdc_archive 'CCDC 626742' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 Ga I3 O2' _chemical_formula_weight 626.63 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4458(15) _cell_length_b 18.197(4) _cell_length_c 12.271(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.13(3) _cell_angle_gamma 90.00 _cell_volume 1658.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 7.233 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.401 _exptl_absorpt_correction_T_max 0.598 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4253 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0884 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2849 _reflns_number_gt 2025 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2849 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 I1 I 0.07000(11) 0.81877(4) 0.20043(6) 0.0391(3) Uani 1 1 d . . . Ga1 Ga 0.24164(16) 0.76434(6) 0.36425(9) 0.0252(3) Uani 1 1 d . . . O1 O 0.2842(10) 0.6650(4) 0.3088(5) 0.0326(19) Uani 1 1 d . . . C1 C 0.2872(14) 0.5997(6) 0.3400(8) 0.023(2) Uani 1 1 d . . . I2 I 0.06452(10) 0.75955(4) 0.53087(5) 0.0339(2) Uani 1 1 d . . . O2 O 0.3089(10) 0.5481(4) 0.2706(5) 0.0304(18) Uani 1 1 d . . . C2 C 0.2687(14) 0.5760(6) 0.4530(8) 0.026(2) Uani 1 1 d . . . H2 H 0.2634 0.6122 0.5085 0.032 Uiso 1 1 calc R . . I3 I 0.55711(10) 0.81173(4) 0.40023(6) 0.0361(3) Uani 1 1 d . . . C3 C 0.2591(14) 0.5059(6) 0.4797(8) 0.029(3) Uani 1 1 d . . . H3 H 0.2735 0.4710 0.4235 0.034 Uiso 1 1 calc R . . C4 C 0.2287(13) 0.4775(6) 0.5876(8) 0.025(2) Uani 1 1 d . . . C5 C 0.1844(14) 0.5218(6) 0.6743(9) 0.033(3) Uani 1 1 d . . . H5 H 0.1756 0.5735 0.6645 0.039 Uiso 1 1 calc R . . C6 C 0.1531(15) 0.4914(6) 0.7750(8) 0.031(3) Uani 1 1 d . . . H6 H 0.1223 0.5217 0.8338 0.037 Uiso 1 1 calc R . . C7 C 0.1678(15) 0.4150(6) 0.7881(9) 0.034(3) Uani 1 1 d . . . H7 H 0.1462 0.3937 0.8566 0.040 Uiso 1 1 calc R . . C8 C 0.2124(14) 0.3706(7) 0.7047(8) 0.033(3) Uani 1 1 d . . . H8 H 0.2240 0.3190 0.7153 0.040 Uiso 1 1 calc R . . C9 C 0.2409(15) 0.4018(6) 0.6038(9) 0.029(3) Uani 1 1 d . . . H9 H 0.2692 0.3710 0.5449 0.035 Uiso 1 1 calc R . . C10 C 0.3225(17) 0.5678(6) 0.1554(8) 0.034(3) Uani 1 1 d . . . H10A H 0.4384 0.5929 0.1460 0.041 Uiso 1 1 calc R . . H10B H 0.2233 0.6014 0.1306 0.041 Uiso 1 1 calc R . . C11 C 0.3110(17) 0.4990(7) 0.0910(9) 0.045(3) Uani 1 1 d . . . H11A H 0.4092 0.4660 0.1166 0.068 Uiso 1 1 calc R . . H11B H 0.3211 0.5104 0.0136 0.068 Uiso 1 1 calc R . . H11C H 0.1951 0.4750 0.1000 0.068 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 I1 0.0465(6) 0.0359(5) 0.0333(4) 0.0087(4) -0.0083(3) 0.0013(4) Ga1 0.0314(7) 0.0193(6) 0.0247(6) -0.0002(5) 0.0004(5) 0.0005(5) O1 0.040(5) 0.023(4) 0.034(4) 0.009(4) 0.001(3) 0.003(4) C1 0.025(6) 0.018(6) 0.027(5) -0.001(5) -0.001(4) 0.000(5) I2 0.0376(5) 0.0362(5) 0.0281(4) -0.0066(3) 0.0033(3) 0.0031(4) O2 0.050(5) 0.023(4) 0.018(3) -0.001(3) -0.003(3) 0.002(4) C2 0.023(6) 0.031(7) 0.024(5) -0.005(5) -0.003(4) 0.001(5) I3 0.0327(5) 0.0296(5) 0.0454(5) 0.0001(3) -0.0019(3) -0.0032(4) C3 0.043(7) 0.018(6) 0.024(5) -0.008(5) -0.002(5) -0.001(5) C4 0.023(6) 0.022(6) 0.029(6) 0.000(5) -0.003(4) -0.008(5) C5 0.030(7) 0.026(7) 0.041(6) -0.003(5) -0.007(5) -0.006(5) C6 0.046(7) 0.027(6) 0.021(5) 0.008(5) 0.006(5) 0.004(6) C7 0.033(7) 0.041(7) 0.027(6) 0.013(6) 0.003(5) 0.004(6) C8 0.030(7) 0.028(7) 0.043(7) -0.004(6) 0.012(5) -0.001(5) C9 0.036(7) 0.019(6) 0.033(6) -0.005(5) 0.002(5) -0.002(5) C10 0.050(8) 0.025(7) 0.029(6) 0.003(5) 0.009(5) 0.007(6) C11 0.054(8) 0.050(9) 0.032(6) -0.013(6) 0.006(5) -0.013(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Ga1 2.5071(15) . ? Ga1 O1 1.966(8) . ? Ga1 I3 2.5113(15) . ? Ga1 I2 2.5130(15) . ? O1 C1 1.247(12) . ? C1 O2 1.286(12) . ? C1 C2 1.468(13) . ? O2 C10 1.469(11) . ? C2 C3 1.320(15) . ? C3 C4 1.454(14) . ? C4 C5 1.393(14) . ? C4 C9 1.393(14) . ? C5 C6 1.388(15) . ? C6 C7 1.403(15) . ? C7 C8 1.363(15) . ? C8 C9 1.393(14) . ? C10 C11 1.480(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ga1 I1 99.86(19) . . ? O1 Ga1 I3 101.8(2) . . ? I1 Ga1 I3 114.94(6) . . ? O1 Ga1 I2 110.9(2) . . ? I1 Ga1 I2 113.52(5) . . ? I3 Ga1 I2 114.07(5) . . ? C1 O1 Ga1 140.2(7) . . ? O1 C1 O2 119.5(9) . . ? O1 C1 C2 124.7(9) . . ? O2 C1 C2 115.8(9) . . ? C1 O2 C10 118.6(8) . . ? C3 C2 C1 122.0(10) . . ? C2 C3 C4 125.8(10) . . ? C5 C4 C9 118.7(10) . . ? C5 C4 C3 123.4(10) . . ? C9 C4 C3 117.9(10) . . ? C6 C5 C4 120.8(11) . . ? C5 C6 C7 118.7(11) . . ? C8 C7 C6 121.5(10) . . ? C7 C8 C9 119.1(11) . . ? C8 C9 C4 121.2(10) . . ? O2 C10 C11 107.6(9) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.079 _refine_diff_density_min -2.100 _refine_diff_density_rms 0.242