Synthesis of Pyrazinopyrazine-Fused Azaacenes through Direct Condensation Reactions between Quinoxalinediamine and Diketones.
Yuan, Yuping; Lo, Kin-Cheung; Szeto, Lap; Chan, Wai-Kin; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03504

data_4038323
_publ_section_title
;
 Synthesis of Pyrazinopyrazine-Fused Azaacenes through Direct Condensation
 Reactions between Quinoxalinediamine and Diketones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03504
_journal_year                    2020
_chemical_formula_moiety         'C38 H36 Br2 N4 S2, C H Cl3'
_chemical_formula_sum            'C39 H37 Br2 Cl3 N4 S2'
_chemical_formula_weight         892.02
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                87.472(2)
_cell_angle_beta                 85.615(2)
_cell_angle_gamma                85.855(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2425(3)
_cell_length_b                   13.6804(5)
_cell_length_c                   22.8237(10)
_cell_measurement_reflns_used    46633
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.69
_cell_volume                     1936.89(14)
_computing_cell_refinement       'APEX2 (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et. al, 2008)'
_computing_publication_material  'SHELXL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_radiation_monochromator  compact
_diffrn_radiation_source         'micro-focus Mo source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            46633
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.442
_exptl_absorpt_correction_T_max  0.8156
_exptl_absorpt_correction_T_min  0.5249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.00104(16)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         6852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0239
_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^)+(0.0216P)^2^+1.4181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0548
_reflns_number_gt                6046
_reflns_number_total             6852
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo9b03504_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4038323