Substrate-Controlled Domino Reactions of Crotonate-Derived Sulfur Ylides: Synthesis of Benzothiophene Derivatives.
Ding, Wenhuan; Zhang, Youquan; Yu, Aimin; Zhang, Lei; Meng, Xiangtai; The Journal of organic chemistry 83 (2018) 13821–13833; doi:10.1021/acs.joc.8b02152

data_4034849
_publ_section_title
;
 Substrate-Controlled Domino Reactions of Crotonate-Derived Sulfur Ylides:
 Synthesis of Benzothiophene Derivatives.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13821
_journal_page_last               13833
_journal_paper_doi               10.1021/acs.joc.8b02152
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H19 Cl O4 S'
_chemical_formula_sum            'C22 H19 Cl O4 S'
_chemical_formula_weight         414.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-27
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.078(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.068(3)
_cell_length_b                   8.7264(8)
_cell_length_c                   17.6647(17)
_cell_measurement_reflns_used    2059
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1360
_cell_measurement_theta_min      2.6570
_cell_volume                     4436.4(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9701
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.996
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.329
_exptl_absorpt_coefficient_mu    0.289
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4350
_refine_ls_number_restraints     167
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0698P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2470
_reflns_number_total             4350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02152_si_006.cif
_cod_data_source_block           11_sqd
_cod_original_cell_volume        4436.3(7)
_cod_database_code               4034849
_shelx_shelxl_version_number     2016/6
_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, All O(H) groups
2. Restrained distances
 C20A-O4
 1.45 with sigma of 0.02
 C22A-C20A
 1.45 with sigma of 0.02
 C20A-C21A
 1.45 with sigma of 0.02
 C20-O4
 1.45 with sigma of 0.02
 C20-C22
 1.45 with sigma of 0.02
 C20-C21
 1.45 with sigma of 0.02
 C22-C21
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C21, C20, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C20, O4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C21 \\sim C20 \\sim C22: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C20 \\sim O4: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O4 \\sim C20 \\sim C22 \\sim C21 \\sim C22A \\sim C21A \\sim C20A: within 2A
with sigma of 0.0051 and sigma for terminal atoms of 0.02
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O4) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C22A) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C20A) \\sim Ueq:
with sigma of 0.0051 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O4, C20, C22, C21, C22A, C21A, C20A
 with sigma for 1-2 distances of 0.0051 and sigma for 1-3 distances of 0.01
6. Others
 Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(2)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(2)
 Sof(C20A)=Sof(H20A)=1-FVAR(3)
 Sof(C20)=Sof(H20)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C17(H17), C20(H20), C20A(H20A)
7.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
7.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C4(H4), C16(H16), C3(H3), C15(H15), C13(H13), C14(H14)
7.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C22A(H22D,H22E,H22F), C21A(H21D,
 H21E,H21F)
7.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              90226
_shelx_hkl_checksum              35975
_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_void_probe_radius 1.20