Copper-catalyzed tandem arylation–cyclization of 2-alkynylaryl isothiocyanates with diaryliodonium salts: an efficient synthesis of thiochromeno[2,3-b]indoles
Wen, Li-Rong; Shen, Qiang-Yu; Guo, Wei-Si; Li, Ming; Organic Chemistry Frontiers 3 (2016) 870–; doi:10.1039/C6QO00133E

data_1553451
_publ_section_title
;
 Copper-catalyzed tandem arylation--cyclization of 2-alkynylaryl
 isothiocyanates with diaryliodonium salts: an efficient synthesis of
 thiochromeno[2,3-b]indoles
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              870
_journal_paper_doi               10.1039/C6QO00133E
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C22 H17 N O2 S'
_chemical_formula_sum            'C22 H17 N O2 S'
_chemical_formula_weight         359.42
_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
_audit_creation_date             2015-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-25 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                93.084(9)
_cell_angle_beta                 106.290(10)
_cell_angle_gamma                115.259(8)
_cell_formula_units_Z            4
_cell_length_a                   11.0789(15)
_cell_length_b                   11.6353(15)
_cell_length_c                   16.290(3)
_cell_measurement_reflns_used    5670
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4850
_cell_measurement_theta_min      2.1493
_cell_volume                     1786.1(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
scan:
	Number of images: 358
	           Slice: -110.0000 - 69.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.0807
	          2theta: -19.8965
scan:
	Number of images: 336
	           Slice: -110.0000 - 58.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0807
	          2theta: -19.8965
scan:
	Number of images: 282
	           Slice: -80.0000 - 61.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.0807
	          2theta: -19.8965
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0243
_diffrn_orient_matrix_UB_12      0.0771
_diffrn_orient_matrix_UB_13      -0.0680
_diffrn_orient_matrix_UB_21      0.0378
_diffrn_orient_matrix_UB_22      -0.0876
_diffrn_orient_matrix_UB_23      -0.0172
_diffrn_orient_matrix_UB_31      -0.0623
_diffrn_orient_matrix_UB_32      -0.0091
_diffrn_orient_matrix_UB_33      -0.0170
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20502
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.349
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       blcok
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         8089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0487
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7476
_reflns_number_total             8089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00133e2.cif
_cod_data_source_block           a
_cod_database_code               1553451
_diffrn_number_total             8103
_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.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1(H1), C18A(H18A), C22(H22), C10(H10), C12A(H12A), C10A(H10A),
 C11A(H11A), C19A(H19A), C13(H13), C12(H12), C21(H21), C22A(H22A), C13A(H13A),
 C20A(H20A), C11(H11), C4A(H4A), C18(H18), C20(H20), C6(H6), C7(H7), C3A(H3A),
 C6A(H6A), C3(H3), C19(H19), C4(H4), C7A(H7A), C21A(H21A)
2.b Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1(H1B,H1C,H1D)
;
_shelx_res_checksum              89243
_shelx_hkl_checksum              78702
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'