# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- CC-COM-07-2012-035114.cif' _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _database_code_depnum_ccdc_journal ? _publ_section_title ; Palladium(II)-catalysed tandem cyclization of electron-deficient aromatic enynes ; _publ_contact_author_name 'Andrei S.Batsanov' loop_ _publ_author_name N.Wu A.Messinis A.S.Batsanov Z.Yang A.Whiting T.B.Marder #====================================================================== data_2a #TrackingRef '- CC-COM-07-2012-035114.cif' _database_code_depnum_ccdc_archive 'CCDC 852796' _audit_creation_date 2011-09-06 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.08.31 svn.r1945, GUI svn.r3824) ; _chemical_name_common 1-Butylindeno(2,1-c)pyran-3,9-dione _chemical_name_systematic ; 1-Butylindeno[2,1-c]pyran-3,9-dione ; _chemical_formula_moiety 'C16 H14 O3' _chemical_formula_sum 'C16 H14 O3' _chemical_formula_weight 254.27 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 5.3708(2) _cell_length_b 7.2029(3) _cell_length_c 16.9507(8) _cell_angle_alpha 96.461(2) _cell_angle_beta 93.246(2) _cell_angle_gamma 110.029(2) _cell_volume 608.98(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1676 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.79 _cell_measurement_theta_min 2.43 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 268 _exptl_crystal_preparation ; Single-crystal to single-crystal phase transition in 2 stages (ca 280K & ca 240K) ; _exptl_crystal_recrystallization_method 'solvent diffusion: Et2O + n-hexane' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (20 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.84 cm. ; _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 5759 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.22 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_special_details 'Low-temperature phase' _diffrn_standards_number 0 _reflns_number_gt 1491 _reflns_number_total 2151 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.182 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.040 _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0370 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.0911 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.3331(2) 0.67093(18) 0.29843(7) 0.0236(3) Uani 1 1 d . . . O2 O 0.5366(2) 0.71270(19) 0.42052(7) 0.0289(3) Uani 1 1 d . . . O3 O -0.2151(2) 0.86789(19) 0.14982(7) 0.0275(3) Uani 1 1 d . . . C1 C 0.3900(4) 0.7650(3) 0.37911(10) 0.0231(4) Uani 1 1 d . . . C2 C 0.2712(3) 0.9115(3) 0.40094(10) 0.0231(4) Uani 1 1 d . . . H2 H 0.3046 0.9803 0.4538 0.028 Uiso 1 1 d R . . C3 C 0.1122(3) 0.9510(3) 0.34607(10) 0.0206(4) Uani 1 1 d . . . C4 C -0.0241(3) 1.0975(3) 0.35064(10) 0.0208(4) Uani 1 1 d . . . C5 C -0.0283(4) 1.2378(3) 0.41299(11) 0.0252(4) Uani 1 1 d . . . H5 H 0.0681 1.2520 0.4634 0.030 Uiso 1 1 d R . . C6 C -0.1772(4) 1.3568(3) 0.39975(11) 0.0270(5) Uani 1 1 d . . . H6 H -0.1855 1.4520 0.4422 0.032 Uiso 1 1 d R . . C7 C -0.3154(4) 1.3399(3) 0.32539(11) 0.0257(5) Uani 1 1 d . . . H7 H -0.4145 1.4244 0.3178 0.031 Uiso 1 1 d R . . C8 C -0.3092(4) 1.2009(3) 0.26266(11) 0.0237(4) Uani 1 1 d . . . H8 H -0.4023 1.1890 0.2119 0.028 Uiso 1 1 d R . . C9 C -0.1631(3) 1.0795(3) 0.27606(10) 0.0202(4) Uani 1 1 d . . . C10 C -0.1218(3) 0.9212(3) 0.21951(10) 0.0212(4) Uani 1 1 d . . . C11 C 0.0560(3) 0.8461(3) 0.26607(10) 0.0203(4) Uani 1 1 d . . . C12 C 0.1700(3) 0.7116(3) 0.24340(10) 0.0212(4) Uani 1 1 d . . . C13 C 0.1431(4) 0.6016(3) 0.16156(10) 0.0271(5) Uani 1 1 d . . . H13A H 0.2245 0.7004 0.1258 0.032 Uiso 1 1 d R . . H13B H -0.0491 0.5401 0.1430 0.032 Uiso 1 1 d R . . C14 C 0.2644(4) 0.4394(3) 0.15111(10) 0.0238(4) Uani 1 1 d . . . H14A H 0.4586 0.4989 0.1669 0.029 Uiso 1 1 d R . . H14B H 0.1864 0.3390 0.1866 0.029 Uiso 1 1 d R . . C15 C 0.2150(4) 0.3371(3) 0.06527(11) 0.0308(5) Uani 1 1 d . . . H15A H 0.2864 0.4391 0.0298 0.037 Uiso 1 1 d R . . H15B H 0.0205 0.2744 0.0504 0.037 Uiso 1 1 d R . . C16 C 0.3418(4) 0.1780(3) 0.05116(11) 0.0312(5) Uani 1 1 d . . . H16A H 0.3027 0.1179 -0.0050 0.041(3) Uiso 1 1 d R . . H16B H 0.2692 0.0745 0.0851 0.041(3) Uiso 1 1 d R . . H16C H 0.5351 0.2393 0.0644 0.041(3) Uiso 1 1 d 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 0.0266(7) 0.0250(7) 0.0218(7) -0.0002(6) -0.0015(5) 0.0141(6) O2 0.0320(8) 0.0337(8) 0.0265(7) 0.0030(6) -0.0032(6) 0.0200(7) O3 0.0341(8) 0.0309(8) 0.0196(7) -0.0005(6) -0.0022(6) 0.0159(6) C1 0.0240(10) 0.0232(10) 0.0209(10) 0.0009(9) 0.0008(8) 0.0074(9) C2 0.0248(10) 0.0241(10) 0.0208(10) -0.0009(8) 0.0004(8) 0.0107(9) C3 0.0205(10) 0.0192(10) 0.0214(10) 0.0018(8) 0.0029(7) 0.0061(8) C4 0.0214(10) 0.0190(10) 0.0224(10) 0.0028(8) 0.0029(8) 0.0074(8) C5 0.0284(11) 0.0245(11) 0.0231(10) 0.0001(9) 0.0003(8) 0.0113(9) C6 0.0322(11) 0.0206(11) 0.0284(11) -0.0044(9) 0.0014(9) 0.0122(9) C7 0.0266(11) 0.0223(10) 0.0323(11) 0.0046(9) 0.0042(8) 0.0134(9) C8 0.0247(10) 0.0230(10) 0.0244(10) 0.0054(9) 0.0011(8) 0.0090(9) C9 0.0209(10) 0.0191(10) 0.0211(10) 0.0032(8) 0.0022(7) 0.0075(8) C10 0.0210(10) 0.0216(10) 0.0205(10) 0.0035(8) 0.0028(8) 0.0066(8) C11 0.0205(10) 0.0209(10) 0.0192(9) 0.0021(8) 0.0010(7) 0.0073(8) C12 0.0197(10) 0.0219(10) 0.0226(10) 0.0030(8) 0.0019(7) 0.0082(8) C13 0.0314(11) 0.0302(11) 0.0221(10) -0.0026(9) 0.0000(8) 0.0164(9) C14 0.0260(10) 0.0223(10) 0.0238(10) 0.0020(8) 0.0029(8) 0.0098(8) C15 0.0349(12) 0.0352(12) 0.0254(11) -0.0031(9) -0.0013(8) 0.0194(10) C16 0.0413(12) 0.0342(12) 0.0221(10) -0.0037(9) 0.0016(9) 0.0211(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.367(2) . ? O1 C1 1.423(2) . ? O2 C1 1.206(2) . ? O3 C10 1.222(2) . ? C1 C2 1.435(2) . ? C2 C3 1.346(2) . ? C3 C11 1.438(2) . ? C3 C4 1.473(2) . ? C4 C5 1.385(2) . ? C4 C9 1.401(2) . ? C5 C6 1.384(2) . ? C6 C7 1.397(3) . ? C7 C8 1.386(3) . ? C8 C9 1.388(2) . ? C9 C10 1.490(2) . ? C10 C11 1.481(2) . ? C11 C12 1.345(2) . ? C12 C13 1.492(2) . ? C13 C14 1.519(2) . ? C14 C15 1.520(2) . ? C15 C16 1.525(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 C1 123.11(13) . . ? O2 C1 O1 115.30(15) . . ? O2 C1 C2 128.03(17) . . ? O1 C1 C2 116.66(15) . . ? C3 C2 C1 119.63(17) . . ? C2 C3 C11 120.94(16) . . ? C2 C3 C4 131.19(17) . . ? C11 C3 C4 107.85(14) . . ? C5 C4 C9 120.68(17) . . ? C5 C4 C3 130.91(16) . . ? C9 C4 C3 108.40(15) . . ? C6 C5 C4 118.08(17) . . ? C5 C6 C7 121.45(17) . . ? C8 C7 C6 120.55(17) . . ? C7 C8 C9 118.13(16) . . ? C8 C9 C4 121.10(17) . . ? C8 C9 C10 128.99(15) . . ? C4 C9 C10 109.90(15) . . ? O3 C10 C11 128.33(16) . . ? O3 C10 C9 126.65(16) . . ? C11 C10 C9 105.02(14) . . ? C12 C11 C3 120.68(15) . . ? C12 C11 C10 130.43(16) . . ? C3 C11 C10 108.81(14) . . ? C11 C12 O1 118.92(16) . . ? C11 C12 C13 126.38(16) . . ? O1 C12 C13 114.68(15) . . ? C12 C13 C14 117.56(15) . . ? C13 C14 C15 111.58(15) . . ? C14 C15 C16 113.51(15) . . ? 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 C12 C13 C14 8.3(2) . . . . ? C12 C13 C14 C15 178.49(16) . . . . ? C13 C14 C15 C16 177.91(17) . . . . ? #===END data_2c #TrackingRef '- CC-COM-07-2012-035114.cif' _database_code_depnum_ccdc_archive 'CCDC 857641' _audit_creation_date 2011-12-01 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common 1-tert-butylindeno(2,1-c)pyran-3,9-dione _chemical_name_systematic ; 1-tert-butylindeno[2,1-c]pyran-3,9-dione ; _chemical_formula_moiety 'C16 H14 O3' _chemical_formula_sum 'C16 H14 O3' _chemical_formula_weight 254.27 _chemical_melting_point 497.7(5) 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' _space_group_crystal_system orthorhombic _space_group_IT_number 57 _space_group_name_H-M_alt 'P b c m' _space_group_name_Hall '-P 2c 2b' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x, -y+1/2, -z' 5 '-x, -y, -z' 6 'x, y, -z-1/2' 7 'x, -y-1/2, z-1/2' 8 '-x, y-1/2, z' _cell_length_a 12.2272(14) _cell_length_b 14.8729(17) _cell_length_c 6.6914(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1216.9(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1533 _cell_measurement_temperature 120 _cell_measurement_theta_max 26.681 _cell_measurement_theta_min 2.156 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description blade _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f angles and each scan (20 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.85 cm. Poor crystal (split peaks). ; _diffrn_reflns_av_R_equivalents 0.1022 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 5934 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.67 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 840 _reflns_number_total 1169 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.630 (Bruker, 2003)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.355 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.086 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 113 _refine_ls_number_reflns 1169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0469 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1029 _refine_ls_wR_factor_ref 0.1126 _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. All the molecule lies in the mirror plane, except the C(15)H~3~ group, H(14A) and its equivalent. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.57641(14) 0.48408(13) 0.2500 0.0208(5) Uani 1 2 d S . . O2 O 0.40774(15) 0.53785(15) 0.2500 0.0316(6) Uani 1 2 d S . . O3 O 0.93440(15) 0.56500(14) 0.2500 0.0243(5) Uani 1 2 d S . . C1 C 0.5042(2) 0.5575(2) 0.2500 0.0224(7) Uani 1 2 d S . . C2 C 0.5525(2) 0.6448(2) 0.2500 0.0204(6) Uani 1 2 d S . . H2 H 0.5076 0.6969 0.2500 0.025 Uiso 1 2 calc SR . . C3 C 0.6625(2) 0.65280(19) 0.2500 0.0180(6) Uani 1 2 d S . . C4 C 0.7309(2) 0.73380(18) 0.2500 0.0180(6) Uani 1 2 d S . . C5 C 0.7032(2) 0.82455(19) 0.2500 0.0205(6) Uani 1 2 d S . . H5 H 0.6287 0.8429 0.2500 0.025 Uiso 1 2 calc SR . . C6 C 0.7864(2) 0.8874(2) 0.2500 0.0217(7) Uani 1 2 d S . . H6 H 0.7686 0.9496 0.2500 0.026 Uiso 1 2 calc SR . . C7 C 0.8958(2) 0.8615(2) 0.2500 0.0239(7) Uani 1 2 d S . . H7 H 0.9516 0.9060 0.2500 0.029 Uiso 1 2 calc SR . . C8 C 0.9241(2) 0.77072(19) 0.2500 0.0205(7) Uani 1 2 d S . . H8 H 0.9986 0.7526 0.2500 0.025 Uiso 1 2 calc SR . . C9 C 0.8408(2) 0.7077(2) 0.2500 0.0184(6) Uani 1 2 d S . . C10 C 0.8489(2) 0.6078(2) 0.2500 0.0174(6) Uani 1 2 d S . . C11 C 0.7329(2) 0.57468(18) 0.2500 0.0173(6) Uani 1 2 d S . . C12 C 0.6884(2) 0.49149(19) 0.2500 0.0178(6) Uani 1 2 d S . . C13 C 0.7439(2) 0.40025(18) 0.2500 0.0192(6) Uani 1 2 d S . . C14 C 0.6597(2) 0.3238(2) 0.2500 0.0265(7) Uani 1 2 d S . . H14A H 0.6110 0.3276 0.3661 0.040 Uiso 1 1 d R . . H14B H 0.6978 0.2659 0.2500 0.040 Uiso 1 2 d SR . . C15 C 0.81465(15) 0.39230(14) 0.4403(3) 0.0239(5) Uani 1 1 d . . . H15A H 0.8685 0.4411 0.4428 0.036 Uiso 1 1 d R . . H15B H 0.8527 0.3343 0.4404 0.036 Uiso 1 1 d R . . H15C H 0.7677 0.3965 0.5587 0.036 Uiso 1 1 d 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 0.0193(10) 0.0224(12) 0.0206(10) 0.000 0.000 0.0006(8) O2 0.0202(12) 0.0339(13) 0.0406(13) 0.000 0.000 -0.0035(9) O3 0.0234(11) 0.0263(12) 0.0231(10) 0.000 0.000 0.0030(9) C1 0.0224(16) 0.0278(19) 0.0171(14) 0.000 0.000 0.0030(13) C2 0.0229(15) 0.0216(17) 0.0168(13) 0.000 0.000 0.0028(12) C3 0.0251(15) 0.0221(18) 0.0067(12) 0.000 0.000 0.0004(11) C4 0.0258(16) 0.0229(17) 0.0052(12) 0.000 0.000 0.0017(12) C5 0.0281(15) 0.0237(17) 0.0096(12) 0.000 0.000 0.0037(13) C6 0.0342(16) 0.0210(17) 0.0099(13) 0.000 0.000 0.0012(13) C7 0.0331(17) 0.0260(18) 0.0126(13) 0.000 0.000 -0.0060(13) C8 0.0234(15) 0.0248(19) 0.0134(13) 0.000 0.000 -0.0011(12) C9 0.0245(15) 0.0224(17) 0.0082(12) 0.000 0.000 0.0023(12) C10 0.0187(14) 0.0250(17) 0.0085(12) 0.000 0.000 0.0015(12) C11 0.0241(15) 0.0186(15) 0.0092(12) 0.000 0.000 0.0016(12) C12 0.0197(14) 0.0236(17) 0.0101(12) 0.000 0.000 0.0001(12) C13 0.0217(14) 0.0197(16) 0.0164(14) 0.000 0.000 -0.0013(12) C14 0.0309(17) 0.0219(18) 0.0268(16) 0.000 0.000 -0.0011(13) C15 0.0297(11) 0.0245(12) 0.0176(11) 0.0025(9) 0.0004(8) 0.0048(9) _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 1.404(3) . ? O1 C12 1.374(3) . ? O2 C1 1.215(3) . ? O3 C10 1.224(3) . ? C1 C2 1.426(4) . ? C2 H2 0.9500 . ? C2 C3 1.351(4) . ? C3 C4 1.466(4) . ? C3 C11 1.446(4) . ? C4 C5 1.392(4) . ? C4 C9 1.399(4) . ? C5 H5 0.9500 . ? C5 C6 1.383(4) . ? C6 H6 0.9500 . ? C6 C7 1.392(4) . ? C7 H7 0.9500 . ? C7 C8 1.394(4) . ? C8 H8 0.9500 . ? C8 C9 1.385(4) . ? C9 C10 1.489(4) . ? C10 C11 1.501(4) . ? C11 C12 1.352(4) . ? C12 C13 1.517(4) . ? C13 C14 1.534(4) . ? C13 C15 1.544(2) 6_556 ? C13 C15 1.544(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9799 . ? C15 H15A 0.9800 . ? C15 H15B 0.9799 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 C1 124.4(2) . . ? O1 C1 C2 116.6(2) . . ? O2 C1 O1 115.1(3) . . ? O2 C1 C2 128.3(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 129.8(3) . . ? C2 C3 C11 121.4(3) . . ? C11 C3 C4 108.7(2) . . ? C5 C4 C3 131.2(3) . . ? C5 C4 C9 120.2(3) . . ? C9 C4 C3 108.6(2) . . ? C4 C5 H5 120.8 . . ? C6 C5 C4 118.5(3) . . ? C6 C5 H5 120.8 . . ? C5 C6 H6 119.3 . . ? C5 C6 C7 121.3(3) . . ? C7 C6 H6 119.3 . . ? C6 C7 H7 119.8 . . ? C6 C7 C8 120.5(3) . . ? C8 C7 H7 119.8 . . ? C7 C8 H8 120.9 . . ? C9 C8 C7 118.2(3) . . ? C9 C8 H8 120.9 . . ? C4 C9 C10 109.9(2) . . ? C8 C9 C4 121.3(3) . . ? C8 C9 C10 128.8(2) . . ? O3 C10 C9 125.1(2) . . ? O3 C10 C11 129.5(3) . . ? C9 C10 C11 105.4(2) . . ? C3 C11 C10 107.4(2) . . ? C12 C11 C3 119.7(2) . . ? C12 C11 C10 132.9(3) . . ? O1 C12 C13 112.0(2) . . ? C11 C12 O1 118.3(2) . . ? C11 C12 C13 129.7(2) . . ? C12 C13 C14 111.2(2) . . ? C12 C13 C15 108.61(15) . . ? C12 C13 C15 108.60(15) . 6_556 ? C14 C13 C15 108.63(15) . 6_556 ? C14 C13 C15 108.63(15) . . ? C15 C13 C15 111.2(2) . 6_556 ? C13 C14 H14A 111.5 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14A 104.8 . 6_556 ? H14A C14 H14B 109.8 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? #===END data_2d #TrackingRef '- CC-COM-07-2012-035114.cif' _database_code_depnum_ccdc_archive 'CCDC 857642' _audit_creation_date 2011-12-07 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common 1-cyclopentyl-indeno(2,1-c)pyran-3,9-dione _chemical_name_systematic ; 1-cyclopentyl-indeno[2,1-c]pyran-3,9-dione ; _chemical_formula_moiety 'C17 H14 O3' _chemical_formula_sum 'C17 H14 O3' _chemical_formula_weight 266.28 _chemical_melting_point 459.7(5) 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 5.2209(5) _cell_length_b 10.1676(10) _cell_length_c 12.1963(12) _cell_angle_alpha 99.81(2) _cell_angle_beta 93.34(2) _cell_angle_gamma 98.10(2) _cell_volume 629.34(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4484 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.957 _cell_measurement_theta_min 2.421 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.8622 _exptl_absorpt_correction_T_min 0.7760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0515 before and 0.0419 after correction. The Ratio of minimum to maximum transmission is 0.9000. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_unetI/netI 0.0271 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 11692 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 1.70 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 2953 _reflns_number_total 3668 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.434 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.056 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 3668 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0443 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.1449P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1163 _refine_ls_wR_factor_ref 0.1248 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.30693(15) 0.34832(8) 0.21808(7) 0.02163(18) Uani 1 1 d . . . O3 O 1.04049(16) 0.62401(9) 0.36328(7) 0.0282(2) Uani 1 1 d . . . O2 O -0.02739(16) 0.32066(9) 0.09095(7) 0.0274(2) Uani 1 1 d . . . C3 C 0.4994(2) 0.59079(11) 0.16230(9) 0.0193(2) Uani 1 1 d . . . C11 C 0.6327(2) 0.53816(11) 0.24813(9) 0.0194(2) Uani 1 1 d . . . C10 C 0.8730(2) 0.63378(11) 0.29256(9) 0.0207(2) Uani 1 1 d . . . C12 C 0.5315(2) 0.41876(11) 0.27495(9) 0.0195(2) Uani 1 1 d . . . C13 C 0.6335(2) 0.35085(11) 0.36304(9) 0.0207(2) Uani 1 1 d . . . H13 H 0.7943 0.4087 0.4026 0.025 Uiso 1 1 calc R . . C2 C 0.2770(2) 0.52240(11) 0.10629(9) 0.0218(2) Uani 1 1 d . . . H2 H 0.1919 0.5583 0.0497 0.026 Uiso 1 1 calc R . . C1 C 0.1691(2) 0.39397(11) 0.13306(9) 0.0213(2) Uani 1 1 d . . . C4 C 0.6492(2) 0.72154(11) 0.15313(9) 0.0209(2) Uani 1 1 d . . . C8 C 1.0494(2) 0.86443(12) 0.23757(10) 0.0263(2) Uani 1 1 d . . . H8 H 1.1999 0.8812 0.2886 0.032 Uiso 1 1 calc R . . C17 C 0.4343(2) 0.32538(12) 0.45075(9) 0.0234(2) Uani 1 1 d . . . H17A H 0.5025 0.3763 0.5258 0.028 Uiso 1 1 calc R . . H17B H 0.2675 0.3541 0.4298 0.028 Uiso 1 1 calc R . . C14 C 0.7000(2) 0.20949(12) 0.31551(10) 0.0246(2) Uani 1 1 d . . . H14A H 0.5884 0.1677 0.2465 0.030 Uiso 1 1 calc R . . H14B H 0.8842 0.2155 0.2989 0.030 Uiso 1 1 calc R . . C7 C 1.0011(3) 0.95616(12) 0.16904(11) 0.0284(3) Uani 1 1 d . . . H7 H 1.1203 1.0369 0.1733 0.034 Uiso 1 1 calc R . . C5 C 0.6007(2) 0.81336(12) 0.08455(10) 0.0249(2) Uani 1 1 d . . . H5 H 0.4509 0.7964 0.0331 0.030 Uiso 1 1 calc R . . C6 C 0.7800(3) 0.93101(12) 0.09419(11) 0.0282(3) Uani 1 1 d . . . H6 H 0.7509 0.9955 0.0487 0.034 Uiso 1 1 calc R . . C15 C 0.6471(3) 0.12891(12) 0.40829(11) 0.0292(3) Uani 1 1 d . . . H15A H 0.7907 0.1518 0.4683 0.035 Uiso 1 1 calc R . . H15B H 0.6220 0.0306 0.3791 0.035 Uiso 1 1 calc R . . C9 C 0.8700(2) 0.74747(11) 0.22889(9) 0.0217(2) Uani 1 1 d . . . C16 C 0.3967(3) 0.17349(13) 0.45026(13) 0.0339(3) Uani 1 1 d . . . H16A H 0.2439 0.1266 0.3997 0.041 Uiso 1 1 calc R . . H16B H 0.3730 0.1545 0.5263 0.041 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 0.0213(4) 0.0214(4) 0.0220(4) 0.0070(3) -0.0033(3) 0.0008(3) O3 0.0238(4) 0.0317(5) 0.0288(4) 0.0090(4) -0.0048(3) 0.0015(3) O2 0.0257(4) 0.0289(4) 0.0262(4) 0.0077(3) -0.0041(3) -0.0019(3) C3 0.0217(5) 0.0199(5) 0.0178(5) 0.0054(4) 0.0028(4) 0.0054(4) C11 0.0202(5) 0.0195(5) 0.0187(5) 0.0043(4) 0.0001(4) 0.0037(4) C10 0.0209(5) 0.0208(5) 0.0204(5) 0.0038(4) 0.0014(4) 0.0032(4) C12 0.0196(5) 0.0201(5) 0.0186(5) 0.0034(4) -0.0003(4) 0.0037(4) C13 0.0215(5) 0.0194(5) 0.0218(5) 0.0067(4) -0.0017(4) 0.0032(4) C2 0.0230(5) 0.0230(5) 0.0205(5) 0.0071(4) 0.0004(4) 0.0036(4) C1 0.0225(5) 0.0237(5) 0.0180(5) 0.0048(4) -0.0006(4) 0.0041(4) C4 0.0228(5) 0.0201(5) 0.0208(5) 0.0048(4) 0.0041(4) 0.0046(4) C8 0.0255(6) 0.0240(6) 0.0288(6) 0.0039(4) 0.0039(4) 0.0016(4) C17 0.0267(5) 0.0248(5) 0.0206(5) 0.0075(4) 0.0015(4) 0.0061(4) C14 0.0255(5) 0.0224(5) 0.0280(6) 0.0078(4) 0.0025(4) 0.0071(4) C7 0.0313(6) 0.0216(5) 0.0329(6) 0.0066(5) 0.0090(5) 0.0014(4) C5 0.0276(6) 0.0234(5) 0.0259(5) 0.0088(4) 0.0045(4) 0.0058(4) C6 0.0342(6) 0.0234(5) 0.0304(6) 0.0106(5) 0.0093(5) 0.0060(5) C15 0.0317(6) 0.0234(6) 0.0366(7) 0.0133(5) 0.0034(5) 0.0082(5) C9 0.0227(5) 0.0206(5) 0.0223(5) 0.0042(4) 0.0037(4) 0.0039(4) C16 0.0351(7) 0.0278(6) 0.0439(7) 0.0163(5) 0.0138(6) 0.0058(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 C12 1.3668(13) . ? O1 C1 1.4072(13) . ? O3 C10 1.2182(14) . ? O2 C1 1.2100(14) . ? C3 C2 1.3478(16) . ? C3 C11 1.4413(14) . ? C3 C4 1.4695(15) . ? C11 C12 1.3545(15) . ? C11 C10 1.4869(15) . ? C10 C9 1.4997(16) . ? C12 C13 1.4848(14) . ? C13 C14 1.5500(16) . ? C13 C17 1.5625(16) . ? C13 H13 1.0000 . ? C2 C1 1.4452(16) . ? C2 H2 0.9500 . ? C4 C5 1.3941(15) . ? C4 C9 1.3998(16) . ? C8 C9 1.3908(16) . ? C8 C7 1.3927(17) . ? C8 H8 0.9500 . ? C17 C16 1.5280(17) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C14 C15 1.5220(17) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C7 C6 1.3948(19) . ? C7 H7 0.9500 . ? C5 C6 1.3947(17) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C15 C16 1.5307(18) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? 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 C12 O1 C1 123.55(9) . . ? C2 C3 C11 121.33(10) . . ? C2 C3 C4 130.91(10) . . ? C11 C3 C4 107.76(9) . . ? C12 C11 C3 119.77(10) . . ? C12 C11 C10 131.26(10) . . ? C3 C11 C10 108.98(9) . . ? O3 C10 C11 129.06(10) . . ? O3 C10 C9 126.38(11) . . ? C11 C10 C9 104.55(9) . . ? C11 C12 O1 119.28(10) . . ? C11 C12 C13 127.78(10) . . ? O1 C12 C13 112.93(9) . . ? C12 C13 C14 112.68(9) . . ? C12 C13 C17 112.77(9) . . ? C14 C13 C17 105.01(9) . . ? C12 C13 H13 108.7 . . ? C14 C13 H13 108.7 . . ? C17 C13 H13 108.7 . . ? C3 C2 C1 119.42(10) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? O2 C1 O1 115.82(10) . . ? O2 C1 C2 127.54(10) . . ? O1 C1 C2 116.63(10) . . ? C5 C4 C9 120.85(11) . . ? C5 C4 C3 130.29(11) . . ? C9 C4 C3 108.86(10) . . ? C9 C8 C7 117.80(12) . . ? C9 C8 H8 121.1 . . ? C7 C8 H8 121.1 . . ? C16 C17 C13 105.98(9) . . ? C16 C17 H17A 110.5 . . ? C13 C17 H17A 110.5 . . ? C16 C17 H17B 110.5 . . ? C13 C17 H17B 110.5 . . ? H17A C17 H17B 108.7 . . ? C15 C14 C13 104.08(9) . . ? C15 C14 H14A 110.9 . . ? C13 C14 H14A 110.9 . . ? C15 C14 H14B 110.9 . . ? C13 C14 H14B 110.9 . . ? H14A C14 H14B 109.0 . . ? C8 C7 C6 120.89(12) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C4 C5 C6 117.57(11) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C5 C6 C7 121.51(11) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C14 C15 C16 102.75(9) . . ? C14 C15 H15A 111.2 . . ? C16 C15 H15A 111.2 . . ? C14 C15 H15B 111.2 . . ? C16 C15 H15B 111.2 . . ? H15A C15 H15B 109.1 . . ? C8 C9 C4 121.38(11) . . ? C8 C9 C10 128.79(11) . . ? C4 C9 C10 109.83(10) . . ? C17 C16 C15 104.30(10) . . ? C17 C16 H16A 110.9 . . ? C15 C16 H16A 110.9 . . ? C17 C16 H16B 110.9 . . ? C15 C16 H16B 110.9 . . ? H16A C16 H16B 108.9 . . ? #===END data_3e #TrackingRef '- CC-COM-07-2012-035114.cif' _database_code_depnum_ccdc_archive 'CCDC 852797' _audit_creation_date 2011-09-02 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.08.31 svn.r1945, GUI svn.r3824) ; _chemical_name_common 'ethyl 2-(2-(cyclohexylidenemethyl)-1-oxo-1H-inden-3-yl)acetate' _chemical_name_systematic ; ethyl 2-(2-(cyclohexylidenemethyl)-1-oxo-1H-inden-3-yl)acetate ; _chemical_formula_moiety 'C20 H22 O3' _chemical_formula_sum 'C20 H22 O3' _chemical_formula_weight 310.38 _chemical_melting_point 356(1) 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 10.5444(3) _cell_length_b 16.3175(5) _cell_length_c 10.4557(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.377(7) _cell_angle_gamma 90.00 _cell_volume 1625.4(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7068 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.970 _cell_measurement_theta_min 2.475 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description tablet _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (15 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.84 cm. ; _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 22166 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.14 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 3662 _reflns_number_total 4732 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.380 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 296 _refine_ls_number_reflns 4732 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0407 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.0530P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1061 _refine_ls_wR_factor_ref 0.1128 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.24850(8) 0.53509(5) 0.74919(8) 0.02752(19) Uani 1 1 d . . . O2 O 0.12876(8) 0.43701(4) 0.05347(8) 0.02350(17) Uani 1 1 d . . . O3 O 0.21710(7) 0.54992(4) 0.18544(7) 0.02020(16) Uani 1 1 d . . . C1 C 0.20089(10) 0.54284(6) 0.62148(11) 0.0192(2) Uani 1 1 d . . . C2 C 0.19267(10) 0.47752(6) 0.51559(10) 0.01793(19) Uani 1 1 d . . . C3 C 0.12127(10) 0.50937(6) 0.38391(10) 0.01690(19) Uani 1 1 d . . . C4 C 0.08392(10) 0.59612(6) 0.39377(10) 0.01772(19) Uani 1 1 d . . . C5 C 0.00908(11) 0.65155(6) 0.28820(11) 0.0208(2) Uani 1 1 d . . . H5 H -0.0302(13) 0.6358(8) 0.1884(14) 0.023(3) Uiso 1 1 d . . . C6 C -0.01311(12) 0.73013(6) 0.32991(12) 0.0246(2) Uani 1 1 d . . . H6 H -0.0673(14) 0.7702(8) 0.2587(14) 0.029(3) Uiso 1 1 d . . . C7 C 0.03790(12) 0.75192(7) 0.47156(13) 0.0262(2) Uani 1 1 d . . . H7 H 0.0204(15) 0.8061(9) 0.4987(15) 0.037(4) Uiso 1 1 d . . . C8 C 0.11247(11) 0.69488(7) 0.57771(12) 0.0243(2) Uani 1 1 d . . . H8 H 0.1482(14) 0.7085(9) 0.6775(15) 0.030(3) Uiso 1 1 d . . . C9 C 0.13317(10) 0.61765(6) 0.53663(11) 0.0195(2) Uani 1 1 d . . . C10 C 0.24240(10) 0.39393(6) 0.55899(10) 0.0202(2) Uani 1 1 d . . . H10 H 0.2179(14) 0.3706(8) 0.6320(14) 0.025(3) Uiso 1 1 d . . . C11 C 0.31662(10) 0.34703(6) 0.50964(11) 0.0197(2) Uani 1 1 d . . . C12 C 0.37481(11) 0.37611(6) 0.40905(11) 0.0214(2) Uani 1 1 d . . . H12A H 0.3221(14) 0.3487(8) 0.3147(14) 0.024(3) Uiso 1 1 d . . . H12B H 0.3597(13) 0.4376(8) 0.3932(14) 0.027(3) Uiso 1 1 d . . . C13 C 0.53202(11) 0.35628(7) 0.46447(12) 0.0244(2) Uani 1 1 d . . . H13A H 0.5658(15) 0.3731(8) 0.3907(15) 0.032(3) Uiso 1 1 d . . . H13B H 0.5853(14) 0.3914(8) 0.5503(14) 0.030(3) Uiso 1 1 d . . . C14 C 0.56215(12) 0.26602(7) 0.50312(12) 0.0275(2) Uani 1 1 d . . . H14A H 0.5126(15) 0.2320(8) 0.4152(15) 0.033(4) Uiso 1 1 d . . . H14B H 0.6671(17) 0.2567(9) 0.5396(16) 0.042(4) Uiso 1 1 d . . . C15 C 0.50855(12) 0.24051(7) 0.61141(12) 0.0271(2) Uani 1 1 d . . . H15A H 0.5619(14) 0.2721(8) 0.7050(14) 0.027(3) Uiso 1 1 d . . . H15B H 0.5258(15) 0.1806(10) 0.6356(15) 0.039(4) Uiso 1 1 d . . . C16 C 0.35172(12) 0.25913(7) 0.55757(13) 0.0256(2) Uani 1 1 d . . . H16A H 0.3170(15) 0.2474(8) 0.6330(16) 0.036(4) Uiso 1 1 d . . . H16B H 0.3023(14) 0.2214(8) 0.4766(14) 0.027(3) Uiso 1 1 d . . . C17 C 0.06950(11) 0.46458(6) 0.24678(11) 0.01829(19) Uani 1 1 d . . . H17A H -0.0288(14) 0.4806(8) 0.1903(13) 0.026(3) Uiso 1 1 d . . . H17B H 0.0736(13) 0.4047(8) 0.2640(13) 0.024(3) Uiso 1 1 d . . . C18 C 0.14164(10) 0.48098(6) 0.15113(10) 0.01752(19) Uani 1 1 d . . . C19 C 0.28952(11) 0.57161(7) 0.09800(12) 0.0241(2) Uani 1 1 d . . . H19A H 0.2267(14) 0.5600(8) -0.0023(15) 0.027(3) Uiso 1 1 d . . . H19B H 0.3043(15) 0.6313(9) 0.1131(14) 0.033(4) Uiso 1 1 d . . . C20 C 0.42628(13) 0.52631(9) 0.14518(15) 0.0351(3) Uani 1 1 d . . . H20A H 0.4072(17) 0.4666(10) 0.1284(17) 0.047(4) Uiso 1 1 d . . . H20B H 0.4856(18) 0.5346(10) 0.2491(19) 0.050(4) Uiso 1 1 d . . . H20C H 0.473(2) 0.5443(10) 0.0879(19) 0.060(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0252(4) 0.0384(5) 0.0191(4) -0.0011(3) 0.0096(3) 0.0036(3) O2 0.0282(4) 0.0227(4) 0.0206(4) -0.0049(3) 0.0114(3) -0.0021(3) O3 0.0221(3) 0.0199(3) 0.0217(4) -0.0030(3) 0.0123(3) -0.0040(3) C1 0.0160(4) 0.0241(5) 0.0202(5) -0.0018(4) 0.0102(4) -0.0005(4) C2 0.0174(4) 0.0194(4) 0.0198(5) 0.0000(4) 0.0107(4) -0.0004(3) C3 0.0171(4) 0.0163(4) 0.0203(5) -0.0015(3) 0.0108(4) -0.0016(3) C4 0.0177(4) 0.0157(4) 0.0228(5) -0.0012(3) 0.0116(4) -0.0010(3) C5 0.0236(5) 0.0182(5) 0.0238(5) 0.0013(4) 0.0134(4) 0.0004(4) C6 0.0266(5) 0.0181(5) 0.0339(6) 0.0035(4) 0.0175(5) 0.0028(4) C7 0.0280(5) 0.0178(5) 0.0396(6) -0.0053(4) 0.0210(5) -0.0011(4) C8 0.0233(5) 0.0247(5) 0.0286(6) -0.0080(4) 0.0145(4) -0.0026(4) C9 0.0181(4) 0.0207(5) 0.0225(5) -0.0027(4) 0.0114(4) -0.0012(4) C10 0.0208(5) 0.0215(5) 0.0201(5) 0.0046(4) 0.0105(4) 0.0013(4) C11 0.0192(4) 0.0189(5) 0.0210(5) 0.0027(4) 0.0086(4) 0.0005(4) C12 0.0229(5) 0.0210(5) 0.0230(5) 0.0027(4) 0.0124(4) 0.0031(4) C13 0.0220(5) 0.0276(5) 0.0273(5) 0.0025(4) 0.0141(4) 0.0037(4) C14 0.0275(6) 0.0293(6) 0.0281(6) 0.0033(4) 0.0142(5) 0.0102(4) C15 0.0289(6) 0.0254(5) 0.0271(6) 0.0055(4) 0.0120(5) 0.0082(4) C16 0.0284(5) 0.0193(5) 0.0314(6) 0.0057(4) 0.0150(5) 0.0032(4) C17 0.0197(4) 0.0164(4) 0.0196(5) -0.0015(3) 0.0091(4) -0.0018(3) C18 0.0169(4) 0.0169(4) 0.0170(4) 0.0005(3) 0.0056(4) 0.0013(3) C19 0.0252(5) 0.0271(5) 0.0236(5) -0.0001(4) 0.0140(4) -0.0053(4) C20 0.0261(6) 0.0465(8) 0.0384(7) -0.0023(6) 0.0190(5) 0.0005(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 1.2151(12) . ? O2 C18 1.2071(12) . ? O3 C18 1.3351(12) . ? O3 C19 1.4639(12) . ? C1 C2 1.5122(14) . ? C1 C9 1.4980(14) . ? C2 C3 1.3579(14) . ? C2 C10 1.4621(14) . ? C3 C4 1.4847(13) . ? C3 C17 1.4890(13) . ? C4 C5 1.3830(14) . ? C4 C9 1.3997(14) . ? C5 H5 0.978(13) . ? C5 C6 1.4058(14) . ? C6 H6 0.971(13) . ? C6 C7 1.3880(16) . ? C7 H7 0.970(15) . ? C7 C8 1.4029(16) . ? C8 H8 0.971(14) . ? C8 C9 1.3788(14) . ? C10 H10 0.982(13) . ? C10 C11 1.3456(14) . ? C11 C12 1.5036(14) . ? C11 C16 1.5120(14) . ? C12 H12A 1.006(13) . ? C12 H12B 1.019(13) . ? C12 C13 1.5379(14) . ? C13 H13A 1.016(14) . ? C13 H13B 1.009(14) . ? C13 C14 1.5243(16) . ? C14 H14A 1.007(14) . ? C14 H14B 1.016(16) . ? C14 C15 1.5242(16) . ? C15 H15A 1.034(13) . ? C15 H15B 1.006(15) . ? C15 C16 1.5317(16) . ? C16 H16A 1.020(16) . ? C16 H16B 0.994(13) . ? C17 H17A 0.984(13) . ? C17 H17B 0.992(14) . ? C17 C18 1.5173(14) . ? C19 H19A 0.990(14) . ? C19 H19B 0.988(14) . ? C19 C20 1.5031(17) . ? C20 H20A 0.994(16) . ? C20 H20B 1.003(17) . ? C20 H20C 0.973(19) . ? 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 C18 O3 C19 116.51(8) . . ? O1 C1 C2 126.75(9) . . ? O1 C1 C9 127.10(9) . . ? C9 C1 C2 106.11(8) . . ? C3 C2 C1 107.79(8) . . ? C3 C2 C10 129.86(9) . . ? C10 C2 C1 122.00(9) . . ? C2 C3 C4 110.05(8) . . ? C2 C3 C17 127.13(9) . . ? C4 C3 C17 122.42(9) . . ? C5 C4 C3 130.22(9) . . ? C5 C4 C9 120.76(9) . . ? C9 C4 C3 108.98(8) . . ? C4 C5 H5 121.0(7) . . ? C4 C5 C6 117.57(10) . . ? C6 C5 H5 121.4(7) . . ? C5 C6 H6 119.9(8) . . ? C7 C6 C5 121.65(10) . . ? C7 C6 H6 118.5(8) . . ? C6 C7 H7 120.7(8) . . ? C6 C7 C8 120.24(10) . . ? C8 C7 H7 119.0(8) . . ? C7 C8 H8 121.8(8) . . ? C9 C8 C7 118.03(10) . . ? C9 C8 H8 120.2(8) . . ? C4 C9 C1 106.99(8) . . ? C8 C9 C1 131.25(9) . . ? C8 C9 C4 121.73(10) . . ? C2 C10 H10 115.1(8) . . ? C11 C10 C2 127.00(9) . . ? C11 C10 H10 117.9(8) . . ? C10 C11 C12 124.57(9) . . ? C10 C11 C16 120.82(9) . . ? C12 C11 C16 114.58(9) . . ? C11 C12 H12A 109.0(7) . . ? C11 C12 H12B 110.0(7) . . ? C11 C12 C13 111.54(8) . . ? H12A C12 H12B 107.3(10) . . ? C13 C12 H12A 109.2(7) . . ? C13 C12 H12B 109.7(7) . . ? C12 C13 H13A 109.2(8) . . ? C12 C13 H13B 108.3(8) . . ? H13A C13 H13B 106.2(11) . . ? C14 C13 C12 111.82(9) . . ? C14 C13 H13A 111.1(8) . . ? C14 C13 H13B 109.9(8) . . ? C13 C14 H14A 108.9(8) . . ? C13 C14 H14B 108.3(8) . . ? H14A C14 H14B 108.4(12) . . ? C15 C14 C13 111.06(9) . . ? C15 C14 H14A 108.4(8) . . ? C15 C14 H14B 111.8(9) . . ? C14 C15 H15A 110.0(7) . . ? C14 C15 H15B 111.6(8) . . ? C14 C15 C16 111.01(9) . . ? H15A C15 H15B 106.3(11) . . ? C16 C15 H15A 108.3(7) . . ? C16 C15 H15B 109.6(8) . . ? C11 C16 C15 112.48(9) . . ? C11 C16 H16A 108.4(8) . . ? C11 C16 H16B 109.9(8) . . ? C15 C16 H16A 111.6(8) . . ? C15 C16 H16B 106.2(8) . . ? H16A C16 H16B 108.2(11) . . ? C3 C17 H17A 107.8(8) . . ? C3 C17 H17B 109.8(7) . . ? C3 C17 C18 117.89(8) . . ? H17A C17 H17B 108.9(11) . . ? C18 C17 H17A 104.8(7) . . ? C18 C17 H17B 107.4(7) . . ? O2 C18 O3 124.48(9) . . ? O2 C18 C17 123.11(9) . . ? O3 C18 C17 112.39(8) . . ? O3 C19 H19A 108.9(8) . . ? O3 C19 H19B 103.1(8) . . ? O3 C19 C20 111.10(10) . . ? H19A C19 H19B 110.3(11) . . ? C20 C19 H19A 111.5(8) . . ? C20 C19 H19B 111.6(8) . . ? C19 C20 H20A 109.3(10) . . ? C19 C20 H20B 110.8(10) . . ? C19 C20 H20C 108.7(11) . . ? H20A C20 H20B 107.9(13) . . ? H20A C20 H20C 107.8(14) . . ? H20B C20 H20C 112.4(15) . . ? #===END data_2k #TrackingRef '- CC-COM-07-2012-035114.cif' _database_code_depnum_ccdc_archive 'CCDC 895772' _audit_creation_date 2012-08-11 _audit_creation_method ; Olex2 1.2-alpha (compiled 2012.08.08 svn.r2439, GUI svn.r4300) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H10 O3' _chemical_formula_sum 'C18 H10 O3' _chemical_formula_weight 274.26 _chemical_absolute_configuration unk _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.7461(4) _cell_length_b 32.774(3) _cell_length_c 10.2441(10) _cell_angle_alpha 90 _cell_angle_beta 99.745(4) _cell_angle_gamma 90 _cell_volume 1239.6(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5219 _cell_measurement_temperature 100 _cell_measurement_theta_max 65.97 _cell_measurement_theta_min 2.70 _exptl_absorpt_coefficient_mu 0.819 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6805 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2009/1 (Bruker,2010) was used for absorption correction. wR2(int) was 0.1358 before and 0.0570 after correction. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 7 runs of narrow-frame \w-scans (scan width 0.5\% \w, 15 to 60 s exposure), every run at different \f and/or 2\q angles. Crystal to detector distance 4.96 cm. Cobra (Oxford Cryosystems) non-liquid N~2~ open-flow cryostat was used. 1874 unique reflections after merging Friedel equivalents. The crystal showed sigan of pseudo-merohedral twinning by 180\% rotation around the a* axis (twin law 1 0 -1 0 -1 0 0 0 -1), which could not be satisfactorily corrected for due to imperfect overlap of reflections. Intense areas of diffuse scattering effectively bridged Bragg reflections along the b* direction into continuous streaks, possibly indicating incommensurate distortions. ; _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 5216 _diffrn_reflns_sigmaI/netI 0.0376 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 66.780 _diffrn_reflns_theta_min 2.696 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker PLATINUM135 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54188 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'Microstar rotating Cu anode source with cross-coupled G\"obel mirrors' _diffrn_standards_number 0 _reflns_Friedel_coverage 0.302 _reflns_Friedel_fraction_full 0.255 _reflns_Friedel_fraction_max 0.261 _reflns_number_gt 2320 _reflns_number_total 2440 _reflns_special_details ; The reflections were merged according to the crystal class for structure refinement and the calculation of statistics. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. The structure posesses a pseudo-inversion centre at 0.274, 0.3435, 0.254, resulting in the approximate space group P2~1~/n. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'PROTEUM v.2011.2-0 (Bruker, 2011)' _computing_data_collection 'PROTEUM v.2011.2-0 (Bruker, 2011)' _computing_data_reduction 'SAINT v7.60A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, Beta test 2012/4 multi-CPU, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.486 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.121 _refine_ls_abs_structure_details ; Flack x determined using 539 quotients [(I+)-I(-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.3(2) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 3.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 369 _refine_ls_number_reflns 2440 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.1030 _refine_ls_restrained_S_all 3.017 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.008 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3259 _refine_ls_wR_factor_ref 0.3313 _refine_special_details ; ? ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.067(2) 0.7483(2) 0.1101(9) 0.029(2) Uani 1 1 d D . . O2A O -0.209(2) 0.8082(3) 0.0721(11) 0.039(2) Uani 1 1 d D . . O3A O 0.730(2) 0.6729(3) 0.4311(9) 0.037(3) Uani 1 1 d D . . C1A C -0.032(3) 0.7872(4) 0.1531(14) 0.028(3) Uani 1 1 d D . . C2A C 0.087(3) 0.7958(4) 0.2911(13) 0.024(3) Uani 1 1 d D . . H2A H 0.0256 0.8212 0.3259 0.029 Uiso 1 1 calc R . . C3A C 0.284(3) 0.7685(3) 0.3728(13) 0.025(3) Uani 1 1 d D . . C4A C 0.432(3) 0.7700(3) 0.5114(15) 0.024(3) Uani 1 1 d D . . C5A C 0.417(3) 0.8013(4) 0.6030(13) 0.028(3) Uani 1 1 d D . . H5A H 0.3020 0.8265 0.5771 0.033 Uiso 1 1 calc R . . C6A C 0.579(3) 0.7940(4) 0.7346(13) 0.027(3) Uani 1 1 d D . . H6A H 0.5708 0.8146 0.7993 0.032 Uiso 1 1 calc R . . C7A C 0.754(3) 0.7569(3) 0.7727(14) 0.028(3) Uani 1 1 d D . . H7A H 0.8609 0.7530 0.8627 0.034 Uiso 1 1 calc R . . C8A C 0.775(3) 0.7263(4) 0.6833(13) 0.027(3) Uani 1 1 d D . . H8A H 0.8960 0.7014 0.7090 0.032 Uiso 1 1 calc R . . C9A C 0.605(3) 0.7336(3) 0.5497(15) 0.030(3) Uani 1 1 d D . . C10A C 0.588(3) 0.7057(4) 0.4339(14) 0.030(3) Uani 1 1 d D . . C11A C 0.371(3) 0.7285(4) 0.3229(15) 0.029(3) Uani 1 1 d D . . C12A C 0.252(3) 0.7196(3) 0.1955(14) 0.025(3) Uani 1 1 d D . . C13A C 0.301(3) 0.6820(3) 0.1200(13) 0.024(2) Uiso 1 1 d D . . C14A C 0.367(3) 0.6839(4) -0.0084(14) 0.030(3) Uani 1 1 d D . . H14A H 0.3886 0.7097 -0.0488 0.036 Uiso 1 1 calc R . . C15A C 0.404(3) 0.6479(4) -0.0801(12) 0.026(3) Uani 1 1 d D . . H15A H 0.4545 0.6494 -0.1677 0.031 Uiso 1 1 calc R . . C16A C 0.364(3) 0.6104(4) -0.0222(16) 0.035(3) Uani 1 1 d D . . H16A H 0.3866 0.5860 -0.0699 0.042 Uiso 1 1 calc R . . C17A C 0.292(3) 0.6088(4) 0.1075(15) 0.032(3) Uani 1 1 d D . . H17A H 0.2612 0.5830 0.1463 0.038 Uiso 1 1 calc R . . C18A C 0.263(3) 0.6440(3) 0.1808(14) 0.032(3) Uani 1 1 d D . . H18A H 0.2196 0.6424 0.2694 0.039 Uiso 1 1 calc R . . O1B O 0.518(2) 0.4387(2) 0.6012(9) 0.028(2) Uani 1 1 d D . . O2B O 0.241(3) 0.3792(3) 0.5621(9) 0.032(2) Uani 1 1 d D . . O3B O 1.185(2) 0.5149(3) 0.9230(9) 0.037(2) Uani 1 1 d D . . C1B C 0.419(3) 0.4006(3) 0.6437(14) 0.029(3) Uani 1 1 d D . . C2B C 0.541(3) 0.3908(3) 0.7803(13) 0.025(3) Uani 1 1 d D . . H2B H 0.4919 0.3647 0.8140 0.030 Uiso 1 1 calc R . . C3B C 0.727(3) 0.4190(3) 0.8605(14) 0.025(3) Uani 1 1 d D . . C4B C 0.880(3) 0.4176(4) 1.0027(16) 0.030(3) Uani 1 1 d D . . C5B C 0.876(3) 0.3863(4) 1.0967(15) 0.031(3) Uani 1 1 d D . . H5B H 0.7642 0.3608 1.0713 0.038 Uiso 1 1 calc R . . C6B C 1.036(3) 0.3932(4) 1.2245(15) 0.033(3) Uani 1 1 d D . . H6B H 1.0315 0.3724 1.2891 0.040 Uiso 1 1 calc R . . C7B C 1.205(3) 0.4303(4) 1.2618(13) 0.032(3) Uani 1 1 d D . . H7B H 1.3107 0.4346 1.3517 0.038 Uiso 1 1 calc R . . C8B C 1.222(3) 0.4611(4) 1.1698(13) 0.027(3) Uani 1 1 d D . . H8B H 1.3418 0.4861 1.1954 0.032 Uiso 1 1 calc R . . C9B C 1.062(3) 0.4546(4) 1.0427(16) 0.033(3) Uani 1 1 d D . . C10B C 1.038(3) 0.4815(3) 0.9245(14) 0.027(3) Uani 1 1 d D . . C11B C 0.815(3) 0.4588(3) 0.8130(14) 0.027(3) Uani 1 1 d D . . C12B C 0.703(3) 0.4676(3) 0.6819(14) 0.025(3) Uani 1 1 d D . . C13B C 0.751(3) 0.5055(3) 0.6115(14) 0.027(2) Uiso 1 1 d D . . C14B C 0.825(3) 0.5027(4) 0.4784(13) 0.028(3) Uani 1 1 d D . . H14B H 0.8494 0.4767 0.4399 0.033 Uiso 1 1 calc R . . C15B C 0.859(3) 0.5374(4) 0.4067(14) 0.033(3) Uani 1 1 d D . . H15B H 0.9038 0.5358 0.3183 0.039 Uiso 1 1 calc R . . C16B C 0.828(3) 0.5754(4) 0.4674(14) 0.031(3) Uani 1 1 d D . . H16B H 0.8585 0.5996 0.4195 0.037 Uiso 1 1 calc R . . C17B C 0.754(3) 0.5787(4) 0.5939(13) 0.031(3) Uani 1 1 d D . . H17B H 0.7250 0.6047 0.6319 0.037 Uiso 1 1 calc R . . C18B C 0.723(3) 0.5435(3) 0.6643(14) 0.029(3) Uani 1 1 d D . . H18B H 0.6795 0.5457 0.7528 0.035 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 O1A 0.030(4) 0.030(4) 0.026(5) -0.002(4) -0.001(4) 0.000(3) O2A 0.039(4) 0.032(5) 0.043(7) 0.002(4) 0.004(5) 0.007(4) O3A 0.038(5) 0.030(5) 0.044(7) -0.003(4) 0.012(5) 0.007(3) C1A 0.032(6) 0.025(6) 0.032(8) -0.005(6) 0.015(6) -0.004(4) C2A 0.024(5) 0.030(6) 0.021(7) -0.006(5) 0.010(5) 0.000(4) C3A 0.019(5) 0.032(6) 0.020(7) 0.000(6) -0.006(5) -0.003(4) C4A 0.022(5) 0.023(5) 0.031(8) 0.002(5) 0.016(5) -0.005(4) C5A 0.032(6) 0.037(7) 0.016(7) -0.004(6) 0.013(6) -0.004(5) C6A 0.035(6) 0.029(6) 0.021(7) -0.003(5) 0.015(6) -0.009(5) C7A 0.027(5) 0.031(6) 0.027(8) 0.003(6) 0.007(5) -0.001(4) C8A 0.028(5) 0.030(6) 0.023(7) 0.005(5) 0.009(6) -0.003(4) C9A 0.041(6) 0.024(6) 0.033(8) 0.001(5) 0.028(7) -0.002(4) C10A 0.031(6) 0.030(6) 0.031(9) 0.009(6) 0.014(6) 0.001(5) C11A 0.025(5) 0.027(6) 0.040(9) 0.001(6) 0.018(6) 0.002(4) C12A 0.021(5) 0.022(6) 0.032(8) 0.003(5) 0.007(5) 0.001(4) C14A 0.028(5) 0.026(6) 0.034(8) 0.000(6) -0.001(6) -0.004(4) C15A 0.030(5) 0.035(7) 0.014(6) -0.006(5) 0.009(5) -0.002(4) C16A 0.027(5) 0.024(6) 0.053(10) -0.008(7) 0.002(7) 0.004(4) C17A 0.035(6) 0.023(6) 0.040(9) -0.004(6) 0.013(6) -0.004(4) C18A 0.035(6) 0.024(6) 0.034(9) 0.003(5) -0.003(6) 0.001(5) O1B 0.042(5) 0.018(4) 0.028(5) -0.001(4) 0.017(4) -0.006(3) O2B 0.052(5) 0.027(5) 0.017(5) -0.002(4) 0.006(4) -0.004(3) O3B 0.050(5) 0.023(4) 0.042(7) 0.001(4) 0.013(5) -0.004(3) C1B 0.035(6) 0.021(6) 0.028(8) -0.002(5) -0.001(6) -0.003(4) C2B 0.033(6) 0.017(5) 0.028(8) -0.010(5) 0.014(6) -0.003(4) C3B 0.022(5) 0.017(5) 0.036(8) -0.003(5) 0.007(6) 0.008(4) C4B 0.022(5) 0.028(6) 0.040(9) -0.004(6) 0.009(6) 0.002(4) C5B 0.030(5) 0.026(6) 0.040(9) 0.001(6) 0.011(6) -0.001(4) C6B 0.034(6) 0.031(6) 0.036(9) 0.008(6) 0.012(7) 0.001(5) C7B 0.036(6) 0.043(7) 0.017(7) 0.000(6) 0.006(6) 0.004(5) C8B 0.033(6) 0.026(6) 0.025(8) 0.000(6) 0.015(6) 0.001(4) C9B 0.035(6) 0.029(6) 0.038(9) 0.004(6) 0.018(7) 0.005(5) C10B 0.027(5) 0.024(6) 0.030(8) -0.007(5) 0.006(6) -0.002(4) C11B 0.023(5) 0.024(6) 0.034(9) -0.004(6) 0.004(6) -0.001(4) C12B 0.024(5) 0.022(6) 0.029(8) -0.004(5) 0.005(6) 0.003(4) C14B 0.030(5) 0.033(6) 0.024(7) -0.008(5) 0.014(5) -0.002(5) C15B 0.036(6) 0.032(6) 0.032(7) -0.002(6) 0.010(6) -0.004(5) C16B 0.027(5) 0.036(7) 0.032(8) 0.006(6) 0.012(6) 0.003(5) C17B 0.042(7) 0.029(6) 0.021(7) -0.002(6) 0.001(6) -0.004(5) C18B 0.017(5) 0.032(6) 0.041(9) -0.001(6) 0.013(6) 0.003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C1A 1.418(14) . ? O1A C12A 1.389(13) . ? O2A C1A 1.190(16) . ? O3A C10A 1.202(15) . ? C1A C2A 1.435(18) . ? C2A C3A 1.356(17) . ? C3A C4A 1.435(19) . ? C3A C11A 1.464(17) . ? C4A C5A 1.397(17) . ? C4A C9A 1.382(16) . ? C5A C6A 1.402(18) . ? C6A C7A 1.403(18) . ? C7A C8A 1.370(17) . ? C8A C9A 1.428(19) . ? C9A C10A 1.491(18) . ? C10A C11A 1.483(19) . ? C11A C12A 1.337(19) . ? C12A C13A 1.481(16) . ? C13A C14A 1.381(17) . ? C13A C18A 1.413(16) . ? C14A C15A 1.408(17) . ? C15A C16A 1.382(17) . ? C16A C17A 1.402(19) . ? C17A C18A 1.389(17) . ? O1B C1B 1.392(13) . ? O1B C12B 1.365(14) . ? O2B C1B 1.202(15) . ? O3B C10B 1.226(14) . ? C1B C2B 1.434(18) . ? C2B C3B 1.349(16) . ? C3B C4B 1.473(19) . ? C3B C11B 1.449(15) . ? C4B C5B 1.410(18) . ? C4B C9B 1.416(16) . ? C5B C6B 1.36(2) . ? C6B C7B 1.395(18) . ? C7B C8B 1.390(17) . ? C8B C9B 1.355(19) . ? C9B C10B 1.489(19) . ? C10B C11B 1.495(18) . ? C11B C12B 1.369(18) . ? C12B C13B 1.462(16) . ? C13B C14B 1.439(16) . ? C13B C18B 1.372(16) . ? C14B C15B 1.372(18) . ? C15B C16B 1.406(17) . ? C16B C17B 1.374(17) . ? C17B C18B 1.375(17) . ? 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 C12A O1A C1A 122.9(11) . . ? O1A C1A C2A 115.4(11) . . ? O2A C1A O1A 116.5(12) . . ? O2A C1A C2A 128.1(12) . . ? C3A C2A C1A 121.6(11) . . ? C2A C3A C4A 131.8(12) . . ? C2A C3A C11A 120.4(12) . . ? C4A C3A C11A 107.8(11) . . ? C5A C4A C3A 129.6(11) . . ? C9A C4A C3A 109.6(12) . . ? C9A C4A C5A 120.8(13) . . ? C4A C5A C6A 117.4(12) . . ? C5A C6A C7A 121.4(12) . . ? C8A C7A C6A 121.7(12) . . ? C7A C8A C9A 116.8(11) . . ? C4A C9A C8A 121.9(12) . . ? C4A C9A C10A 110.4(13) . . ? C8A C9A C10A 127.7(11) . . ? O3A C10A C9A 127.4(13) . . ? O3A C10A C11A 128.3(13) . . ? C11A C10A C9A 104.3(10) . . ? C3A C11A C10A 107.9(12) . . ? C12A C11A C3A 118.6(12) . . ? C12A C11A C10A 133.4(12) . . ? O1A C12A C13A 109.1(11) . . ? C11A C12A O1A 121.0(10) . . ? C11A C12A C13A 129.8(11) . . ? C14A C13A C12A 121.3(10) . . ? C14A C13A C18A 120.4(11) . . ? C18A C13A C12A 118.2(11) . . ? C13A C14A C15A 120.6(11) . . ? C16A C15A C14A 119.6(11) . . ? C15A C16A C17A 119.5(11) . . ? C18A C17A C16A 121.8(12) . . ? C17A C18A C13A 118.1(13) . . ? C12B O1B C1B 124.5(11) . . ? O1B C1B C2B 116.7(11) . . ? O2B C1B O1B 116.8(12) . . ? O2B C1B C2B 126.5(12) . . ? C3B C2B C1B 119.1(11) . . ? C2B C3B C4B 131.0(11) . . ? C2B C3B C11B 122.4(12) . . ? C11B C3B C4B 106.7(10) . . ? C5B C4B C3B 130.5(11) . . ? C5B C4B C9B 119.1(13) . . ? C9B C4B C3B 110.4(12) . . ? C6B C5B C4B 118.8(12) . . ? C5B C6B C7B 120.8(12) . . ? C8B C7B C6B 121.3(13) . . ? C9B C8B C7B 118.3(12) . . ? C4B C9B C10B 108.2(12) . . ? C8B C9B C4B 121.7(12) . . ? C8B C9B C10B 130.1(12) . . ? O3B C10B C9B 125.0(13) . . ? O3B C10B C11B 129.0(13) . . ? C9B C10B C11B 105.9(10) . . ? C3B C11B C10B 108.8(11) . . ? C12B C11B C3B 118.0(11) . . ? C12B C11B C10B 133.1(11) . . ? O1B C12B C11B 119.2(10) . . ? O1B C12B C13B 112.5(11) . . ? C11B C12B C13B 128.3(11) . . ? C14B C13B C12B 118.3(10) . . ? C18B C13B C12B 123.6(13) . . ? C18B C13B C14B 118.1(12) . . ? C15B C14B C13B 120.4(12) . . ? C14B C15B C16B 118.4(12) . . ? C17B C16B C15B 122.1(12) . . ? C16B C17B C18B 118.5(11) . . ? C13B C18B C17B 122.5(13) . . ? _shelx_res_checksum 72506 _shelx_res_file ; TITL 12srv111 in P21 #4 CELL 1.54188 3.7461 32.7736 10.2441 90 99.745 90 ZERR 4 0.0004 0.0033 0.001 0 0.004 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O UNIT 72 40 12 L.S. 30 PLAN 7 TEMP -173.12 rem SIMU C13 C18 C17 C16 C15 C14 REM reset to P21 #4 BOND fmap 2 acta REM I:/andrei/datasets/12srv111/12srv111.hkl WGHT 0.100000 FVAR 0.64318 O1A 3 0.066711 0.748328 0.110123 11.00000 0.02989 0.02981 = 0.02619 -0.00162 -0.00136 0.00029 O2A 3 -0.209126 0.808169 0.072101 11.00000 0.03947 0.03191 = 0.04339 0.00209 0.00422 0.00700 O3A 3 0.730284 0.672927 0.431128 11.00000 0.03838 0.03031 = 0.04421 -0.00264 0.01170 0.00687 C1A 1 -0.031990 0.787205 0.153145 11.00000 0.03157 0.02529 = 0.03162 -0.00485 0.01471 -0.00358 C2A 1 0.086707 0.795792 0.291055 11.00000 0.02357 0.03044 = 0.02102 -0.00607 0.00987 -0.00038 AFIX 43 H2A 2 0.025595 0.821226 0.325923 11.00000 -1.20000 AFIX 0 C3A 1 0.284020 0.768472 0.372804 11.00000 0.01923 0.03233 = 0.02032 0.00036 -0.00641 -0.00321 C4A 1 0.432079 0.769982 0.511415 11.00000 0.02246 0.02271 = 0.03058 0.00230 0.01557 -0.00499 C5A 1 0.417373 0.801268 0.602990 11.00000 0.03229 0.03711 = 0.01633 -0.00435 0.01264 -0.00437 AFIX 43 H5A 2 0.301958 0.826503 0.577091 11.00000 -1.20000 AFIX 0 C6A 1 0.579460 0.793992 0.734554 11.00000 0.03454 0.02917 = 0.02082 -0.00289 0.01464 -0.00866 AFIX 43 H6A 2 0.570832 0.814572 0.799251 11.00000 -1.20000 AFIX 0 C7A 1 0.754190 0.756941 0.772673 11.00000 0.02711 0.03101 = 0.02741 0.00335 0.00749 -0.00148 AFIX 43 H7A 2 0.860864 0.753012 0.862726 11.00000 -1.20000 AFIX 0 C8A 1 0.774872 0.726291 0.683349 11.00000 0.02850 0.03023 = 0.02319 0.00478 0.00914 -0.00331 AFIX 43 H8A 2 0.896046 0.701359 0.709025 11.00000 -1.20000 AFIX 0 C9A 1 0.605433 0.733631 0.549732 11.00000 0.04139 0.02370 = 0.03290 0.00136 0.02791 -0.00227 C10A 1 0.588365 0.705739 0.433895 11.00000 0.03120 0.02971 = 0.03075 0.00858 0.01370 0.00128 C11A 1 0.370808 0.728474 0.322859 11.00000 0.02513 0.02658 = 0.03991 0.00095 0.01770 0.00239 C12A 1 0.252188 0.719582 0.195500 11.00000 0.02149 0.02210 = 0.03225 0.00292 0.00736 0.00103 C13A 1 0.301185 0.682047 0.120024 11.00000 0.02424 C14A 1 0.367335 0.683901 -0.008418 11.00000 0.02825 0.02600 = 0.03395 0.00021 -0.00056 -0.00394 AFIX 43 H14A 2 0.388611 0.709686 -0.048771 11.00000 -1.20000 AFIX 0 C15A 1 0.403523 0.647922 -0.080092 11.00000 0.02992 0.03529 = 0.01369 -0.00621 0.00851 -0.00203 AFIX 43 H15A 2 0.454507 0.649384 -0.167714 11.00000 -1.20000 AFIX 0 C16A 1 0.364419 0.610447 -0.022196 11.00000 0.02665 0.02373 = 0.05332 -0.00771 0.00206 0.00414 AFIX 43 H16A 2 0.386601 0.585986 -0.069937 11.00000 -1.20000 AFIX 0 C17A 1 0.291782 0.608827 0.107503 11.00000 0.03484 0.02292 = 0.04024 -0.00364 0.01298 -0.00361 AFIX 43 H17A 2 0.261202 0.583006 0.146284 11.00000 -1.20000 AFIX 0 C18A 1 0.263321 0.643961 0.180830 11.00000 0.03530 0.02397 = 0.03429 0.00269 -0.00311 0.00145 AFIX 43 H18A 2 0.219622 0.642428 0.269383 11.00000 -1.20000 AFIX 0 O1B 3 0.517924 0.438717 0.601224 11.00000 0.04209 0.01804 = 0.02821 -0.00126 0.01680 -0.00619 O2B 3 0.241345 0.379245 0.562107 11.00000 0.05193 0.02675 = 0.01728 -0.00235 0.00592 -0.00351 O3B 3 1.185456 0.514892 0.922982 11.00000 0.04961 0.02254 = 0.04217 0.00142 0.01346 -0.00435 C1B 1 0.419134 0.400647 0.643672 11.00000 0.03535 0.02070 = 0.02789 -0.00212 -0.00141 -0.00343 C2B 1 0.541270 0.390783 0.780346 11.00000 0.03346 0.01695 = 0.02810 -0.01017 0.01375 -0.00328 AFIX 43 H2B 2 0.491907 0.364746 0.813963 11.00000 -1.20000 AFIX 0 C3B 1 0.727150 0.418974 0.860484 11.00000 0.02225 0.01687 = 0.03604 -0.00307 0.00731 0.00815 C4B 1 0.879511 0.417644 1.002749 11.00000 0.02204 0.02832 = 0.03997 -0.00427 0.00943 0.00234 C5B 1 0.875879 0.386283 1.096677 11.00000 0.03010 0.02578 = 0.04018 0.00116 0.01054 -0.00144 AFIX 43 H5B 2 0.764169 0.360814 1.071341 11.00000 -1.20000 AFIX 0 C6B 1 1.035546 0.393154 1.224540 11.00000 0.03415 0.03139 = 0.03647 0.00846 0.01250 0.00099 AFIX 43 H6B 2 1.031477 0.372412 1.289053 11.00000 -1.20000 AFIX 0 C7B 1 1.204859 0.430289 1.261767 11.00000 0.03616 0.04336 = 0.01714 -0.00015 0.00595 0.00386 AFIX 43 H7B 2 1.310686 0.434591 1.351720 11.00000 -1.20000 AFIX 0 C8B 1 1.221684 0.461105 1.169803 11.00000 0.03311 0.02599 = 0.02470 0.00035 0.01474 0.00120 AFIX 43 H8B 2 1.341794 0.486103 1.195417 11.00000 -1.20000 AFIX 0 C9B 1 1.062321 0.454561 1.042692 11.00000 0.03547 0.02899 = 0.03757 0.00442 0.01808 0.00455 C10B 1 1.038431 0.481502 0.924480 11.00000 0.02658 0.02377 = 0.03045 -0.00679 0.00608 -0.00201 C11B 1 0.815379 0.458759 0.812983 11.00000 0.02343 0.02415 = 0.03444 -0.00412 0.00404 -0.00114 C12B 1 0.703102 0.467572 0.681877 11.00000 0.02378 0.02205 = 0.02891 -0.00391 0.00460 0.00309 C13B 1 0.751379 0.505451 0.611511 11.00000 0.02656 C14B 1 0.824821 0.502692 0.478381 11.00000 0.02954 0.03292 = 0.02433 -0.00777 0.01427 -0.00232 AFIX 43 H14B 2 0.849450 0.476689 0.439894 11.00000 -1.20000 AFIX 0 C15B 1 0.859468 0.537409 0.406730 11.00000 0.03626 0.03185 = 0.03183 -0.00182 0.00999 -0.00356 AFIX 43 H15B 2 0.903783 0.535810 0.318266 11.00000 -1.20000 AFIX 0 C16B 1 0.827779 0.575417 0.467442 11.00000 0.02728 0.03610 = 0.03249 0.00630 0.01167 0.00264 AFIX 43 H16B 2 0.858470 0.599610 0.419471 11.00000 -1.20000 AFIX 0 C17B 1 0.753848 0.578694 0.593924 11.00000 0.04168 0.02946 = 0.02114 -0.00235 0.00139 -0.00370 AFIX 43 H17B 2 0.724953 0.604679 0.631889 11.00000 -1.20000 AFIX 0 C18B 1 0.722640 0.543536 0.664278 11.00000 0.01733 0.03184 = 0.04077 -0.00055 0.01324 0.00268 AFIX 43 H18B 2 0.679547 0.545696 0.752776 11.00000 -1.20000 AFIX 0 HKLF 4 REM sad in P21 #4 REM R1 = 0.1030 for 2320 Fo > 4sig(Fo) and 0.1054 for all 2440 data REM 369 parameters refined using 1 restraints END WGHT 0.0000 27.8503 REM Highest difference peak 0.486, deepest hole -0.537, 1-sigma level 0.121 Q1 1 0.8104 0.5734 0.7199 11.00000 0.05 0.42 Q2 1 0.9975 0.6609 0.3718 11.00000 0.05 0.41 Q3 1 1.2207 0.4620 1.2937 11.00000 0.05 0.40 Q4 1 0.1357 0.5657 -0.0738 11.00000 0.05 0.40 Q5 1 -0.2139 0.8429 0.0589 11.00000 0.05 0.39 Q6 1 0.2013 0.6807 0.0069 11.00000 0.05 0.38 Q7 1 1.2513 0.4842 0.9765 11.00000 0.05 0.38 ; _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2012-4 #===END