Diversity-oriented synthesis of tetrathia[8]circulenes by sequential C-H borylation and annulation
Shohei Kato; Yuma Serizawa; Daisuke Sakamaki; Shu Seki; Yoshihiro Miyake; Hiroshi Shinokubo; Chem.Commun. 51 (2015) 16944–; doi:10.1039/C5cc06921A

data_7118096
_publ_section_title
;
 Diversity-oriented synthesis of tetrathia[8]circulenes by sequential C-H
 borylation and annulation
;
_journal_name_full               Chem.Commun.
_journal_page_first              16944
_journal_paper_doi               10.1039/C5cc06921A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C15.5 H9 Cl S2'
_chemical_formula_weight         294.80
_chemical_name_common            5
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-06 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.926(9)
_cell_length_b                   10.268(4)
_cell_length_c                   9.738(3)
_cell_measurement_reflns_used    8661
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.08
_cell_volume                     2592.3(16)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20243
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.8326
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.96(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5937
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1213P)^2^+1.1808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                5434
_reflns_number_total             5937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06921a2.cif
_cod_data_source_block           shelxl_2
_cod_original_cell_volume        2592.3(15)
_cod_original_formula_sum        'C15.50 H9 Cl S2'
_cod_database_code               7118096