Synthesis of Thiophene-Based TAK-779 Analogues by C-H Arylation
Anna Junker; Junichiro Yamaguchi; Kenichiro Itami; Bernhard Wünsch; Journal of Organic Chemistry 78 (2013) 5579–5586; doi:10.1021/jo400692p

data_4028318
_publ_section_title
;
 Synthesis of Thiophene-Based TAK-779 Analogues by C-H Arylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5579
_journal_page_last               5586
_journal_paper_doi               10.1021/jo400692p
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C18 H18 O2 S'
_chemical_formula_weight         298.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.13(7)
_cell_angle_beta                 88.64(7)
_cell_angle_gamma                67.30(5)
_cell_formula_units_Z            4
_cell_length_a                   9.917(18)
_cell_length_b                   10.332(18)
_cell_length_c                   17.37(4)
_cell_measurement_reflns_used    2788
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.3426
_cell_measurement_theta_min      3.1630
_cell_volume                     1641(6)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    ORTEP-III
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_av_sigmaI/netI    0.1192
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15111
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       Block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.1788
_refine_ls_R_factor_gt           0.1153
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1379P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2623
_refine_ls_wR_factor_ref         0.3115
_reflns_number_gt                3305
_reflns_number_total             5638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400692p_si_002.cif
_cod_data_source_block           qq
_cod_original_cell_volume        1642(5)
_cod_database_code               4028318