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_4034844
_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         'C18 H18 O5 S'
_chemical_formula_sum            'C18 H18 O5 S'
_chemical_formula_weight         346.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                111.653(2)
_cell_angle_beta                 95.303(2)
_cell_angle_gamma                114.760(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8988(7)
_cell_length_b                   10.1507(7)
_cell_length_c                   10.2605(8)
_cell_measurement_reflns_used    7941
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.441
_cell_measurement_theta_min      3.590
_cell_volume                     832.05(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17253
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.1955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                2931
_reflns_number_total             3824
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02152_si_002.cif
_cod_data_source_block           111
_cod_original_cell_volume        832.05(10)
_cod_database_code               4034844
_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.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'