#------------------------------------------------------------------------------ #$Date: 2025-08-21 22:26:11 +0100 (Thu, 21 Aug 2025) $ #$Revision: 301853 $ #$URL: svn://www.crystallography.net/cod/cif/7/10/88/7108824.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7108824 loop_ _publ_author_name 'Wei Wang' 'Junfeng Wang' 'Shuo Zhou' 'Qi Sun' 'Zemei Ge' 'Xin Wang' 'Runtao Li' _publ_section_title ; An efficient organocatalytic enantioselective Michael addition of aryl methyl ketones with 2-furanones: highly functionalized chiral 3,4-substituted lactones ; _journal_issue 13 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1333 _journal_page_last 1335 _journal_paper_doi 10.1039/c2cc35488h _journal_volume 49 _journal_year 2013 _chemical_absolute_configuration ad _chemical_formula_moiety 'C17 H19 Br O5 ' _chemical_formula_sum 'C17 H19 Br O5' _chemical_formula_weight 383.24 _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.941(3) _cell_length_b 11.055(4) _cell_length_c 22.261(8) _cell_measurement_reflns_used 1859 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 72.0 _cell_measurement_theta_min 27.3 _cell_volume 1708.1(11) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_molecular_graphics ORTEPII(Johnson,1976)andPLUTON(Spek,1990) _computing_publication_material 'SHELXL97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 295(2) _diffrn_detector_area_resol_mean 22.2222 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'MicroMax 002+' _diffrn_measurement_method \f\k _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 15439 _diffrn_reflns_theta_full 72.64 _diffrn_reflns_theta_max 72.64 _diffrn_reflns_theta_min 3.97 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.480 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.572 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_meas 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.382 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.063 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.008(19) _refine_ls_extinction_coef 0.0102(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3330 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0347 _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^)+(0.0493P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.0894 _reflns_number_gt 3012 _reflns_number_total 3330 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c2cc35488h.txt _cod_data_source_block 5391 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius ; _cod_original_formula_sum 'C17 H19 Br O5 ' _cod_database_code 7108824 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 Br1 Br -0.77497(5) -0.01458(3) 0.052370(19) 0.08309(18) Uani 1 1 d . O1 O -0.8462(3) -0.7108(2) -0.28318(8) 0.0624(5) Uani 1 1 d . O2 O -0.5895(5) -0.8296(3) -0.27661(11) 0.0950(9) Uani 1 1 d . O3 O -0.7025(3) -0.84403(18) -0.13523(10) 0.0669(5) Uani 1 1 d . O4 O -0.4235(3) -0.74248(17) -0.12710(7) 0.0508(4) Uani 1 1 d . O5 O -0.7621(3) -0.58075(15) -0.06987(7) 0.0571(5) Uani 1 1 d . C2 C -0.6843(4) -0.7486(3) -0.25677(11) 0.0594(7) Uani 1 1 d . C3 C -0.6446(4) -0.6751(3) -0.19998(10) 0.0462(5) Uani 1 1 d . H3A H -0.5365 -0.6197 -0.2067 0.055 Uiso 1 1 calc R C4 C -0.8314(4) -0.6036(2) -0.19145(9) 0.0408(5) Uani 1 1 d . H4A H -0.9182 -0.6521 -0.1664 0.049 Uiso 1 1 calc R C5 C -0.9173(4) -0.5979(3) -0.25533(10) 0.0493(6) Uani 1 1 d . C6 C -0.8113(4) -0.4795(2) -0.16256(9) 0.0463(5) Uani 1 1 d . H6A H -0.7042 -0.4372 -0.1811 0.056 Uiso 1 1 calc R H6B H -0.9272 -0.4331 -0.1704 0.056 Uiso 1 1 calc R C7 C -0.7783(3) -0.4854(2) -0.09533(9) 0.0434(5) Uani 1 1 d . C8 C -0.7712(4) -0.3680(2) -0.06135(9) 0.0442(5) Uani 1 1 d . C9 C -0.7708(4) -0.3718(2) 0.00097(10) 0.0545(6) Uani 1 1 d . H9A H -0.7717 -0.4462 0.0204 0.065 Uiso 1 1 calc R C10 C -0.7691(4) -0.2670(3) 0.03448(11) 0.0601(7) Uani 1 1 d . H10A H -0.7672 -0.2705 0.0762 0.072 Uiso 1 1 calc R C11 C -0.7701(4) -0.1585(2) 0.00583(13) 0.0586(6) Uani 1 1 d . C12 C -0.7682(5) -0.1494(2) -0.05586(14) 0.0687(8) Uani 1 1 d . H12A H -0.7660 -0.0744 -0.0747 0.082 Uiso 1 1 calc R C13 C -0.7696(5) -0.2564(2) -0.08914(12) 0.0613(7) Uani 1 1 d . H13A H -0.7695 -0.2524 -0.1309 0.074 Uiso 1 1 calc R C14 C -0.5965(4) -0.7631(2) -0.15000(11) 0.0484(6) Uani 1 1 d . C15 C -0.3648(4) -0.8211(3) -0.07812(12) 0.0604(7) Uani 1 1 d . H15A H -0.3939 -0.9046 -0.0879 0.073 Uiso 1 1 calc R H15B H -0.4340 -0.7998 -0.0418 0.073 Uiso 1 1 calc R C16 C -0.1535(5) -0.8062(3) -0.06860(12) 0.0577(7) Uani 1 1 d . H16A H -0.1123 -0.8578 -0.0364 0.087 Uiso 1 1 calc R H16B H -0.1261 -0.7235 -0.0586 0.087 Uiso 1 1 calc R H16C H -0.0861 -0.8277 -0.1047 0.087 Uiso 1 1 calc R C17 C -1.1325(5) -0.6037(3) -0.25453(15) 0.0699(8) Uani 1 1 d . H17A H -1.1804 -0.6002 -0.2950 0.105 Uiso 1 1 calc R H17B H -1.1824 -0.5365 -0.2320 0.105 Uiso 1 1 calc R H17C H -1.1729 -0.6779 -0.2361 0.105 Uiso 1 1 calc R C18 C -0.8416(6) -0.4947(3) -0.29362(11) 0.0751(9) Uani 1 1 d . H18A H -0.9010 -0.4976 -0.3326 0.113 Uiso 1 1 calc R H18B H -0.7045 -0.5022 -0.2979 0.113 Uiso 1 1 calc R H18C H -0.8715 -0.4190 -0.2747 0.113 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 Br1 0.0664(2) 0.0586(2) 0.1242(3) -0.04434(18) -0.01465(17) 0.00597(14) O1 0.0729(12) 0.0601(13) 0.0543(8) -0.0171(8) -0.0031(9) 0.0068(10) O2 0.104(2) 0.098(2) 0.0834(13) -0.0285(14) 0.0115(13) 0.0398(17) O3 0.0617(12) 0.0485(11) 0.0906(12) 0.0157(9) 0.0019(10) -0.0082(10) O4 0.0505(9) 0.0472(10) 0.0547(8) 0.0105(8) 0.0002(7) 0.0022(8) O5 0.0830(13) 0.0365(9) 0.0519(7) 0.0031(6) -0.0072(9) 0.0015(10) C2 0.0622(16) 0.0599(17) 0.0560(12) -0.0088(12) 0.0067(12) 0.0083(15) C3 0.0412(12) 0.0484(14) 0.0490(10) 0.0030(11) 0.0032(9) -0.0008(10) C4 0.0440(12) 0.0350(12) 0.0434(9) 0.0018(9) 0.0016(8) -0.0034(10) C5 0.0572(14) 0.0418(14) 0.0490(10) -0.0033(10) -0.0039(10) 0.0019(11) C6 0.0547(12) 0.0381(12) 0.0460(10) 0.0029(9) -0.0013(9) -0.0022(11) C7 0.0440(10) 0.0385(12) 0.0477(9) -0.0001(9) 0.0009(8) 0.0004(11) C8 0.0447(12) 0.0379(12) 0.0501(10) -0.0026(9) -0.0027(10) -0.0019(10) C9 0.0678(16) 0.0436(13) 0.0521(10) -0.0025(10) 0.0004(12) -0.0008(13) C10 0.0603(16) 0.0598(17) 0.0602(12) -0.0156(12) -0.0002(12) -0.0002(14) C11 0.0470(14) 0.0482(14) 0.0806(15) -0.0209(12) -0.0070(13) 0.0043(12) C12 0.083(2) 0.0355(13) 0.0875(17) -0.0008(12) -0.0159(18) -0.0015(14) C13 0.0828(19) 0.0376(12) 0.0634(12) -0.0011(10) -0.0106(14) -0.0023(15) C14 0.0478(13) 0.0404(14) 0.0569(11) -0.0002(11) 0.0040(10) 0.0046(11) C15 0.0630(17) 0.064(2) 0.0540(11) 0.0148(12) 0.0033(12) 0.0106(14) C16 0.0696(17) 0.0455(15) 0.0579(12) 0.0043(12) -0.0113(12) -0.0003(13) C17 0.0622(17) 0.067(2) 0.0810(16) -0.0098(16) -0.0184(15) 0.0045(16) C18 0.108(2) 0.065(2) 0.0524(12) 0.0159(13) -0.0058(14) -0.010(2) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 O1 C5 111.1(2) C14 O4 C15 116.1(2) O2 C2 O1 122.3(3) O2 C2 C3 127.2(3) O1 C2 C3 110.5(2) C14 C3 C2 107.9(2) C14 C3 C4 115.27(19) C2 C3 C4 103.0(2) C14 C3 H3A 110.2 C2 C3 H3A 110.2 C4 C3 H3A 110.2 C6 C4 C3 116.1(2) C6 C4 C5 112.8(2) C3 C4 C5 103.53(18) C6 C4 H4A 108.0 C3 C4 H4A 108.0 C5 C4 H4A 108.0 O1 C5 C17 107.6(2) O1 C5 C18 106.5(2) C17 C5 C18 112.6(3) O1 C5 C4 102.9(2) C17 C5 C4 111.9(2) C18 C5 C4 114.5(2) C7 C6 C4 113.08(19) C7 C6 H6A 109.0 C4 C6 H6A 109.0 C7 C6 H6B 109.0 C4 C6 H6B 109.0 H6A C6 H6B 107.8 O5 C7 C8 121.12(18) O5 C7 C6 121.2(2) C8 C7 C6 117.7(2) C13 C8 C9 118.3(2) C13 C8 C7 123.1(2) C9 C8 C7 118.5(2) C10 C9 C8 121.1(2) C10 C9 H9A 119.5 C8 C9 H9A 119.5 C11 C10 C9 119.2(2) C11 C10 H10A 120.4 C9 C10 H10A 120.4 C10 C11 C12 122.2(2) C10 C11 Br1 118.9(2) C12 C11 Br1 118.9(2) C11 C12 C13 117.9(3) C11 C12 H12A 121.0 C13 C12 H12A 121.0 C8 C13 C12 121.3(3) C8 C13 H13A 119.3 C12 C13 H13A 119.3 O3 C14 O4 125.2(2) O3 C14 C3 122.9(2) O4 C14 C3 111.9(2) O4 C15 C16 108.5(3) O4 C15 H15A 110.0 C16 C15 H15A 110.0 O4 C15 H15B 110.0 C16 C15 H15B 110.0 H15A C15 H15B 108.4 C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C5 C17 H17A 109.5 C5 C17 H17B 109.5 H17A C17 H17B 109.5 C5 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C5 C18 H18A 109.5 C5 C18 H18B 109.5 H18A C18 H18B 109.5 C5 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C11 1.899(2) O1 C2 1.335(4) O1 C5 1.478(3) O2 C2 1.196(4) O3 C14 1.205(3) O4 C14 1.324(3) O4 C15 1.453(3) O5 C7 1.202(3) C2 C3 1.528(4) C3 C14 1.515(4) C3 C4 1.531(3) C3 H3A 0.9800 C4 C6 1.522(3) C4 C5 1.543(3) C4 H4A 0.9800 C5 C17 1.496(5) C5 C18 1.518(4) C6 C7 1.516(3) C6 H6A 0.9700 C6 H6B 0.9700 C7 C8 1.503(3) C8 C13 1.380(4) C8 C9 1.388(3) C9 C10 1.378(4) C9 H9A 0.9300 C10 C11 1.358(4) C10 H10A 0.9300 C11 C12 1.377(4) C12 C13 1.395(4) C12 H12A 0.9300 C13 H13A 0.9300 C15 C16 1.491(5) C15 H15A 0.9700 C15 H15B 0.9700 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C17 H17A 0.9600 C17 H17B 0.9600 C17 H17C 0.9600 C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 102193443