Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation.
Barrett, Matthew J.; Davies, Paul W.; Grainger, Richard S.; Organic & biomolecular chemistry 13 (2015) 8676–8686; doi:10.1039/c5ob01241d

data_7154576
_publ_section_title
;
 Regioselective functionalisation of dibenzothiophenes through
 gold-catalysed intermolecular alkyne oxyarylation.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8676
_journal_page_last               8686
_journal_paper_doi               10.1039/c5ob01241d
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C22 H20 O4 S'
_chemical_formula_sum            'C22 H20 O4 S'
_chemical_formula_weight         380.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-05 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                75.079(5)
_cell_angle_beta                 73.655(4)
_cell_angle_gamma                75.040(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0122(4)
_cell_length_b                   10.2941(6)
_cell_length_c                   10.6266(6)
_cell_measurement_reflns_used    4308
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0910
_cell_measurement_theta_min      4.3970
_cell_volume                     895.60(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.1768
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -63.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   57.0000    0.0000 91

  2 omega  -95.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  125.0000   60.0000 92

  3 omega -115.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000 -150.0000 96

  4 omega   35.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  -30.0000 85

  5 omega   26.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000   30.0000 83

  6 omega   46.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -180.0000 44

  7 omega   36.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -15.0000   30.0000 115

  8 omega   43.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   30.0000 37

  9 omega   36.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 63

 10 omega   88.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000 -150.0000 88

 11 omega   42.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000  120.0000 96
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0415374000
_diffrn_orient_matrix_UB_12      0.0407873000
_diffrn_orient_matrix_UB_13      -0.1538776000
_diffrn_orient_matrix_UB_21      0.0359370000
_diffrn_orient_matrix_UB_22      0.1352104000
_diffrn_orient_matrix_UB_23      0.0092792000
_diffrn_orient_matrix_UB_31      0.1733308000
_diffrn_orient_matrix_UB_32      -0.0710165000
_diffrn_orient_matrix_UB_33      -0.0022882000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4979
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         4.425
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0322P)^2^+0.4861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3020
_reflns_number_total             3193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01241d2.cif
_cod_data_source_block           17a
_cod_depositor_comments          'Adding full bibliography for 7154576.cif.'
_cod_database_code               7154576
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C22 H20 O4 S'
_shelx_estimated_absorpt_t_max   0.784
_shelx_estimated_absorpt_t_min   0.658
_reflns_odcompleteness_completeness 97.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B), C20(H20A,
 H20B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C17(H17), C18(H18)
;
_shelx_res_checksum              35599
_olex2_submission_special_instructions 'No special instructions were received'