Electrochemical stereoselective synthesis of polysubstituted 1,4-dicarbonyl <i>Z</i>-alkenes <i>via</i> three-component coupling of sulfoxonium ylides and alkynes with water.
Li, Hao-Ran; Ran, Yi-An; Zhu, Yu-Yi; Guo, Weisi; Ni, Shao-Fei; Wen, Li-Rong; Li, Ming; Zhang, Lin-Bao; Chemical science 15 (2024) 8156–8162; doi:10.1039/d4sc01141d

data_1571488
_publ_section_title
;
 Electrochemical stereoselective synthesis of polysubstituted
 1,4-dicarbonyl <i>Z</i>-alkenes <i>via</i> three-component coupling of
 sulfoxonium ylides and alkynes with water.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              8156
_journal_page_last               8162
_journal_paper_doi               10.1039/d4sc01141d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-15 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.2970(3)
_cell_length_b                   11.4089(5)
_cell_length_c                   29.4395(11)
_cell_measurement_reflns_used    6964
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      30.9790
_cell_measurement_theta_min      2.7880
_cell_volume                     2786.73(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -101.00  77.00   0.50    8.00    --  -11.60  45.00  30.00  356
  2  \w    -25.00   8.00   0.50    8.00    --  -11.60  45.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0724614000
_diffrn_orient_matrix_UB_12      0.0189014000
_diffrn_orient_matrix_UB_13      0.0105389000
_diffrn_orient_matrix_UB_21      0.0261846000
_diffrn_orient_matrix_UB_22      -0.0242167000
_diffrn_orient_matrix_UB_23      0.0209162000
_diffrn_orient_matrix_UB_31      0.0368760000
_diffrn_orient_matrix_UB_32      0.0541246000
_diffrn_orient_matrix_UB_33      0.0056328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16298
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.086
_diffrn_reflns_theta_min         2.768
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.7767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3255
_reflns_number_total             3902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01141d2.cif
_cod_data_source_block           mx10483
_cod_depositor_comments
'Adding full bibliography for 1571488--1571489.cif.'
_cod_database_code               1571488
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              85764
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.694
_oxdiff_exptl_absorpt_empirical_full_min 0.601