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_4034846
_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 O7 S'
_chemical_formula_sum            'C18 H18 O7 S'
_chemical_formula_weight         378.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.549(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9450(17)
_cell_length_b                   9.9498(15)
_cell_length_c                   18.210(3)
_cell_measurement_reflns_used    2060
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.7000
_cell_measurement_theta_min      2.9940
_cell_volume                     1751.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -75.00 106.00   1.00    6.00    --   30.00  54.00 240.00  181
  2  \w    -41.00  26.00   1.00    6.00    --   30.00  54.00   0.00   67
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0693888000
_diffrn_orient_matrix_UB_12      -0.0232924000
_diffrn_orient_matrix_UB_13      0.0091168000
_diffrn_orient_matrix_UB_21      0.0242581000
_diffrn_orient_matrix_UB_22      0.0672288000
_diffrn_orient_matrix_UB_23      0.0026059000
_diffrn_orient_matrix_UB_31      -0.0001097000
_diffrn_orient_matrix_UB_32      0.0008420000
_diffrn_orient_matrix_UB_33      0.0389312000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6473
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.151
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.326
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.326
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0721
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2443
_reflns_number_total             3083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02152_si_007.cif
_cod_data_source_block           8
_cod_database_code               4034846
_reflns_odcompleteness_completeness 86.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.14
_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:
 C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00P(H00N,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00J(H00J), C00L(H00L)
2.d Idealised Me refined as rotating group:
 C00M(H00A,H00B,H00D), C00N(H00E,H00G,H00H), C00O(H00I,H00K,H00M), C00Q(H00P,
 H00Q,H00R)
;
_shelx_shelxl_version_number     2014/7
_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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.520