Anti-addition of Dimethylsulfoxonium Methylide to Acyclic α,β-Unsaturated Ketones and Its Application in Formal Synthesis of an Eicosanoid.
Angamuthu, Venkatachalam; Chang, Wen-Jung; Hou, Duen-Ren; ACS omega 2 (2017) 4088–4099; doi:10.1021/acsomega.7b00663

data_4516892
_publ_section_title
;
 Anti-addition of Dimethylsulfoxonium Methylide to Acyclic
 \a,\b-Unsaturated Ketones and Its Application in Formal Synthesis of an
 Eicosanoid.
;
_journal_issue                   8
_journal_name_full               'ACS omega'
_journal_page_first              4088
_journal_page_last               4099
_journal_paper_doi               10.1021/acsomega.7b00663
_journal_volume                  2
_journal_year                    2017
_chemical_formula_sum            'C23 H29 N O3'
_chemical_formula_weight         367.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.499(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4742(5)
_cell_length_b                   9.8102(4)
_cell_length_c                   17.1419(8)
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.44
_cell_volume                     2039.78(15)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.906
_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  0.0177
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20304
_diffrn_reflns_point_group_measured_fraction_full 0.803
_diffrn_reflns_point_group_measured_fraction_max 0.722
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_min         1.679
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.006(2)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         7339
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+1.1377P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.1971
_reflns_Friedel_coverage         0.508
_reflns_Friedel_fraction_full    0.629
_reflns_Friedel_fraction_max     0.516
_reflns_number_gt                5823
_reflns_number_total             7339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b00663_si_002.cif
_cod_data_source_block           16JN28_0m
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C46 H58 N2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     734.94
_cod_database_code               4516892
_shelxl_version_number           2013-2
_shelx_res_checksum              89056
_shelx_hkl_checksum              24031