Synthesis of γ-Lactones by TBAI-Promoted Intermolecular Carboesterification of Carboxylic Acids with Alkenes and Alcohols.
Chen, Rongxiang; Wang, Kai-Kai; Wang, Zhan-Yong; Miao, Changqing; Wang, Doudou; Zhang, An-An; Liu, Lantao; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02568

data_4037655
_publ_section_title
;
 Synthesis of \g-Lactones by TBAI-Promoted Intermolecular
 Carboesterification of Carboxylic Acids with Alkenes and Alcohols.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02568
_journal_year                    2019
_chemical_formula_sum            'C13 H14 O4'
_chemical_formula_weight         234.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                99.691(2)
_cell_angle_beta                 100.013(2)
_cell_angle_gamma                115.188(2)
_cell_formula_units_Z            4
_cell_length_a                   11.0013(16)
_cell_length_b                   11.2543(16)
_cell_length_c                   11.7014(18)
_cell_measurement_reflns_used    3175
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.17
_cell_volume                     1242.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7485
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.829
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.2611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3851
_reflns_number_total             5403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02568_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C26 H28 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     468.48
_cod_database_code               4037655
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              94771
_shelx_hkl_checksum              74012