Stereoconvergent Conjugate Addition of Arylboronic Acids to α-Angelica Lactone Derivatives: Synthesis of Stereochemically Complex γ-Butyrolactones
Griswold, Jessica A.; Johnson, Jeffrey S.; ACS Catalysis  (2019) 11614–; doi:10.1021/acscatal.9b04405

data_4516231
_publ_section_title
;
 Stereoconvergent Conjugate Addition of Arylboronic Acids to \a-Angelica
 Lactone Derivatives: Synthesis of Stereochemically Complex
 \g-Butyrolactones
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11614
_journal_paper_doi               10.1021/acscatal.9b04405
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H14 O2'
_chemical_formula_sum            'C12 H14 O2'
_chemical_formula_weight         190.24
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2019-05-28
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1055(2)
_cell_length_b                   7.4185(3)
_cell_length_c                   22.4266(8)
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1015.78(6)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21221
_diffrn_reflns_theta_full        72.329
_diffrn_reflns_theta_max         72.329
_diffrn_reflns_theta_min         3.942
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block fragment'
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details 'Flack (1983), 806 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0352
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.0005430
_refine_ls_shift/su_mean         0.0000505
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.17P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0865
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0865
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                1967
_reflns_number_total             2007
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0338
_oxford_refine_ls_scale          0.2903(4)
_oxford_reflns_number_all        2000
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '19032_0m in P2(1)2(1)2(1)'
_cod_data_source_file            cs9b04405_si_003.cif
_cod_data_source_block           19032
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4516231