Rh(III)-catalysed C–H/C–H cross-coupling of S-aryl sulfoximines with thiophenes: facile access to [1]benzothieno[3,2-b][1]benzothiophene (BTBT) and benzothiazines
Yang, Chengyong; Liu, Zheng; Cheng, Rui; Du, Jiping; Ran, Chunhao; Wu, Di; Lan, Jingbo; Chemical Communications  (2022) –; doi:10.1039/D2CC02232J

data_7130235
_publ_section_title
;
 Rh(III)-catalysed C--H/C--H cross-coupling of S-aryl sulfoximines with
 thiophenes: facile access to [1]benzothieno[3,2-b][1]benzothiophene
 (BTBT) and benzothiazines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02232J
_journal_year                    2022
_chemical_formula_moiety         'C16 H15 N O2 S2'
_chemical_formula_sum            'C16 H15 N O2 S2'
_chemical_formula_weight         317.41
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-03-30 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.3910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9599(3)
_cell_length_b                   11.6425(4)
_cell_length_c                   15.6846(4)
_cell_measurement_reflns_used    7670
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.466
_cell_measurement_theta_min      3.110
_cell_volume                     1447.11(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.984
_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  0.0821
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39620
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         3.110
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1159 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.9374.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0374P)^2^+1.0380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2517
_reflns_number_total             3292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02232j2.cif
_cod_data_source_block           mo_yey_4mco_150k_0m_a
_cod_database_code               7130235
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.857
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.9 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
S3 \\sim N2: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.001 within 1.7A
4. Others
 Sof(S1A)=1-FVAR(1)
 Sof(S1)=FVAR(1)
 Sof(C13A)=Sof(H13A)=1-FVAR(2)
 Sof(C13)=Sof(H13)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C13A(H13A)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              67220
_olex2_submission_special_instructions 'No special instructions were received'