Vinylogous Elimination/Heck Coupling/Allylation Domino Reactions: Access to 2-Substituted 2,3-Dihydrobenzofurans and Indolines.
Yang, Jianguo; Mo, Hanjie; Jin, Xiuxiu; Cao, Dongdong; Wu, Haijian; Chen, Di; Wang, Zhiming; The Journal of organic chemistry 83 (2018) 2592–2600; doi:10.1021/acs.joc.7b02986

data_4033517
_publ_section_title
;
 Vinylogous Elimination/Heck Coupling/Allylation Domino Reactions: Access
 to 2-Substituted 2,3-Dihydrobenzofurans and Indolines.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2592
_journal_page_last               2600
_journal_paper_doi               10.1021/acs.joc.7b02986
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C26 H24 Br N O4 S'
_chemical_formula_sum            'C26 H24 Br N O4 S'
_chemical_formula_weight         526.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 117.4870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0516(10)
_cell_length_b                   12.5217(9)
_cell_length_c                   15.0866(11)
_cell_measurement_reflns_used    7444
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.23
_cell_volume                     2354.8(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23536
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.789
_diffrn_reflns_theta_min         2.227
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.868
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0851 before and 0.0283 after correction.
The Ratio of minimum to maximum transmission is 0.6251.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         7290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0373P)^2^+0.9639P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5661
_reflns_number_total             7290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02986_si_002.cif
_cod_data_source_block           dm17013_cmpd_6t
_cod_depositor_comments
'Adding full bibliography for 4033516--4033518.cif.'
_cod_database_code               4033517
_shelx_estimated_absorpt_t_max   0.652
_shelx_estimated_absorpt_t_min   0.578
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              10000
_shelx_hkl_checksum              87847
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'