Pyrazinacenes: Aza Analogues of Acenes
Gary J. Richards; Jonathan P. Hill; Navaneetha K. Subbaiyan; Francis D'Souza; Paul A. Karr; Mark R. J. Elsegood; Simon J. Teat; Toshiyuki Mori; Katsuhiko Ariga; Journal of Organic Chemistry 74 (2009) 8914–8923; doi:10.1021/jo901832n

data_4025082
_publ_section_title
;
Pyrazinacenes: Aza Analogues of Acenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8914
_journal_page_last               8923
_journal_paper_doi               10.1021/jo901832n
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H10 N8'
_chemical_formula_sum            'C22 H10 N8'
_chemical_formula_weight         386.38
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 132.782(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   19.1050(16)
_cell_length_b                   38.439(3)
_cell_length_c                   13.5450(11)
_cell_measurement_reflns_used    7489
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.20
_cell_measurement_theta_min      3.17
_cell_volume                     7300.6(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 2004 (Altomare et al, 2004)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Advanced Light Source station 11.3.1'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43122
_diffrn_reflns_theta_full        30.26
_diffrn_reflns_theta_max         30.26
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1, Sheldrick, G.M., (2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0551P)^2^+2.8041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                5597
_reflns_number_total             8365
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo901832n_si_003.cif
_cod_data_source_block           jph3
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4025082