Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones.
Gharui, Chandan; Prakash, Satya; Chopra, Deepak; Pan, Subhas Chandra; Organic & biomolecular chemistry 18 (2020) 2828–2833; doi:10.1039/d0ob00568a

data_7157419
_publ_section_title
;
 Organocatalytic asymmetric addition of thioglycolates to o-quinone
 methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2828
_journal_page_last               2833
_journal_paper_doi               10.1039/d0ob00568a
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H16 O4 S'
_chemical_formula_sum            'C17 H16 O4 S'
_chemical_formula_weight         316.36
_chemical_name_systematic        P21212
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-21 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.969(3)
_cell_length_b                   34.663(14)
_cell_length_c                   5.361(2)
_cell_measurement_reflns_used    690
_cell_measurement_temperature    100
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      4.62
_cell_volume                     1480.9(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1470
_diffrn_reflns_av_unetI/netI     0.1607
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12986
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.697
_diffrn_reflns_theta_min         4.582
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1029 before and 0.0844 after correction.
The Ratio of minimum to maximum transmission is 0.7717.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_preparation       Synthesis
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 514 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0762
_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^)+(0.0796P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1915
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                2003
_reflns_number_total             3818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00568a2.cif
_cod_data_source_block           ortho1_a
_cod_depositor_comments
'Adding full bibliography for 7157418--7157419.cif.'
_cod_database_code               7157419
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O4B)=Sof(C16B)=Sof(H16C)=Sof(H16D)=Sof(C17B)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=1-FVAR(1)
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(O4A)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C16A(H16A,H16B), C16B(H16C,H16D)
3.b Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C17B(H17D,H17E,H17F)
;
_shelx_res_checksum              84496
_olex2_submission_special_instructions 'No special instructions were received'