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_4038322
_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         'C24 H32 N4 S2'
_chemical_formula_sum            'C24 H32 N4 S2'
_chemical_formula_weight         440.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                77.4125(19)
_cell_angle_beta                 86.990(2)
_cell_angle_gamma                72.2796(18)
_cell_formula_units_Z            2
_cell_length_a                   7.6430(5)
_cell_length_b                   8.3737(5)
_cell_length_c                   18.7590(12)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.937
_cell_measurement_theta_min      2.613
_cell_volume                     1116.00(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2014)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et. al, 2008)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon100 CMOS area detector'
_diffrn_detector_area_resol_mean 1024
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon100'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1845
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28122
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.613
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.9106
_exptl_absorpt_correction_T_min  0.7463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.1687 before and 0.0470 after correction. The Ratio 
of minimum to maximum transmission is 0.8196. The \l/2 correction 
factor is 0.00150.
;
_exptl_crystal_colour            grey
_exptl_crystal_colour_primary    grey
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'The crystal was recrystallized from a chloroform solution.'
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.5196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3574
_reflns_number_total             3930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03504_si_002.cif
_cod_data_source_block           mo_chem0045_c0ma
_cod_original_cell_volume        1116.01(12)
_cod_database_code               4038322
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2C,H2D), C3(H3C,H3D), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-27
_olex2_date_sample_submission    2015-01-24
_olex2_exptl_crystal_mounting_method
;
The crystal was coated in a thin film of Paraton-N oil and mounted 
on Cryo-loop.
;
_olex2_submission_original_sample_id WKC-Y-9.10
_olex2_submission_special_instructions 'No special instructions were received'