Transition-Metal-Free Selective Oxidative C(sp(3))-S/Se Coupling of Oxindoles, Tetralone, and Arylacetamides: Synthesis of Unsymmetrical Organochalcogenides.
Prasad, Ch Durga; Sattar, Moh; Kumar, Sangit; Organic letters 19 (2017) 774–777; doi:10.1021/acs.orglett.6b03735

data_1545454
_publ_section_title
;
 Transition-Metal-Free Selective Oxidative C(sp(3))-S/Se Coupling of
 Oxindoles, Tetralone, and Arylacetamides: Synthesis of Unsymmetrical
 Organochalcogenides.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              774
_journal_page_last               777
_journal_paper_doi               10.1021/acs.orglett.6b03735
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C21.87 H14 Br N O S, 0.18 (H)'
_chemical_formula_sum            'C21.87 H14.18 Br N O S'
_chemical_formula_weight         418.92
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.5547(8)
_cell_length_b                   20.782(2)
_cell_length_c                   21.537(2)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.72
_cell_volume                     3828.9(6)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0000
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5552
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         2.724
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.266
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1103 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.8214.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1691.2
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.557
_refine_diff_density_min         -1.143
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     134
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0831P)^2^+6.8047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3450
_reflns_number_total             4957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03735_si_003.cif
_cod_data_source_block           DP_831
_cod_original_cell_volume        3828.9(7)
_cod_database_code               1545454
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 C19, C20, C21, C18, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C11, C15, C14, C13, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C19, C18, C20, C21, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C19 \\sim C20 \\sim C18 \\sim C17 \\sim C21: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(C11) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(C9A) \\sim Ueq, Uanis(C9B) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
4.a Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C20(H20), C3(H3), C17(H17), C2(H2), C21(H21), C19(H19),
 C18(H18), C15(H15), C14(H14), C11(H11), C13(H13), C12(H12)
;
_shelx_res_checksum              64412
_shelx_hkl_checksum              89226
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'