C-H-Activated Direct Arylation of Strong Benzothiadiazole and Quinoxaline-Based Electron Acceptors.
Zhang, Junxiang; Parker, Timothy C.; Chen, Wayne; Williams, LaRita; Khrustalev, Victor N.; Jucov, Evgheni V.; Barlow, Stephen; Timofeeva, Tatiana V.; Marder, Seth R.; The Journal of organic chemistry 81 (2016) 360–370; doi:10.1021/acs.joc.5b02551

data_4031829
_publ_section_title
;
 C-H-Activated Direct Arylation of Strong Benzothiadiazole and
 Quinoxaline-Based Electron Acceptors.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              360
_journal_page_last               370
_journal_paper_doi               10.1021/acs.joc.5b02551
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H22 N4 S3 Si2'
_chemical_formula_sum            'C22 H22 N4 S3 Si2'
_chemical_formula_weight         494.80
_chemical_name_systematic
; 

4,7-bis(5-(trimethylsilyl)thiophen-2-yl)-5,6-diycanobenzo[c][1,2,5]thiadiazole

;
_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                88.540(4)
_cell_angle_beta                 79.136(3)
_cell_angle_gamma                76.363(4)
_cell_formula_units_Z            2
_cell_length_a                   7.123(2)
_cell_length_b                   10.302(3)
_cell_length_c                   17.193(5)
_cell_measurement_reflns_used    7413
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.59
_cell_measurement_theta_min      4.12
_cell_volume                     1203.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11674
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.893
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0618
_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^)+(0.09P)^2^+3P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                4861
_reflns_number_total             5667
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5b02551_si_001.cif
_cod_data_source_block           8j
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1203.8(6)
_cod_database_code               4031829