Zirconium-mediated coupling reaction for synthesis of substituted thiophene-fused acenes.
Ni, Yang; Nakajima, Kiyohiko; Kanno, Ken-ichiro; Takahashi, Tamotsu; Organic letters 11 (2009) 3702–3705; doi:10.1021/ol900903w

data_1503969
_publ_section_title
;
 Zirconium-mediated coupling reaction for synthesis of substituted
 thiophene-fused acenes.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3702
_journal_page_last               3705
_journal_paper_doi               10.1021/ol900903w
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C44 H48 S'
_chemical_formula_sum            'C44 H48 S'
_chemical_formula_weight         608.88
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                101.824(14)
_cell_angle_beta                 93.497(15)
_cell_angle_gamma                91.387(16)
_cell_formula_units_Z            2
_cell_length_a                   10.481(5)
_cell_length_b                   12.266(5)
_cell_length_c                   13.619(5)
_cell_measurement_reflns_used    8464
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1709.3(12)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1935
_diffrn_reflns_av_sigmaI/netI    0.2993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16763
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0032(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.899
_refine_ls_R_factor_all          0.2419
_refine_ls_R_factor_gt           0.0879
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1634
_refine_ls_wR_factor_ref         0.2259
_reflns_number_gt                2575
_reflns_number_total             7657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900903w_si_002.cif
_cod_data_source_block           tt81rc
_cod_original_cell_volume        1709.2(13)
_cod_database_code               1503969