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#$Date: 2016-03-21 03:18:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178429 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/50/4025083.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025083
loop_
_publ_author_name
'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'
_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 H16 N6 O2'
_chemical_formula_sum            'C22 H16 N6 O2'
_chemical_formula_weight         396.41
_chemical_name_systematic
;
 ?
;
_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                 107.786(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.6352(9)
_cell_length_b                   16.8426(8)
_cell_length_c                   6.6854(3)
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      3.58
_cell_volume                     1890.81(16)
_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    'SHELXL-97 (Sheldrick, 2008)'
_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       'ω 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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11539
_diffrn_reflns_theta_full        30.29
_diffrn_reflns_theta_max         30.29
_diffrn_reflns_theta_min         3.58
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1, Sheldrick, G.M., (2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0067(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0558P)²+0.6265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                1496
_reflns_number_total             2179
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo901832n_si_004.cif
_cod_data_source_block           jph4
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4025083
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16089(9) -0.22900(10) 0.9144(3) 0.0435(4) Uani 1 1 d . . .
H1A H 0.1789 -0.2843 0.9335 0.065 Uiso 1 1 calc R . .
H1B H 0.1795 -0.2010 1.0492 0.065 Uiso 1 1 calc R . .
H1C H 0.1827 -0.2031 0.8126 0.065 Uiso 1 1 calc R . .
O1 O 0.07533(6) -0.22680(6) 0.83813(16) 0.0378(3) Uani 1 1 d . . .
C2 C 0.04297(9) -0.15498(8) 0.8005(2) 0.0319(3) Uani 1 1 d . . .
N1 N 0.08436(7) -0.09086(7) 0.85043(18) 0.0325(3) Uani 1 1 d . . .
C3 C 0.04253(8) -0.02071(8) 0.8016(2) 0.0298(3) Uani 1 1 d . . .
N2 N 0.08355(7) 0.04596(7) 0.85553(18) 0.0318(3) Uani 1 1 d . . .
C4 C 0.04141(8) 0.11347(8) 0.8042(2) 0.0295(3) Uani 1 1 d . . .
N3 N 0.08115(7) 0.18283(7) 0.86798(18) 0.0310(3) Uani 1 1 d . . .
C5 C 0.04148(8) 0.24981(8) 0.8169(2) 0.0307(3) Uani 1 1 d . . .
C6 C 0.08533(9) 0.32239(8) 0.9129(2) 0.0322(3) Uani 1 1 d . . .
C7 C 0.16595(9) 0.32898(9) 0.9300(2) 0.0366(4) Uani 1 1 d . . .
H7 H 0.1903 0.2898 0.8676 0.044 Uiso 1 1 calc R . .
C8 C 0.21102(10) 0.39208(9) 1.0370(3) 0.0421(4) Uani 1 1 d . . .
H8 H 0.2656 0.3967 1.0454 0.051 Uiso 1 1 calc R . .
C9 C 0.17594(10) 0.44808(9) 1.1312(3) 0.0463(4) Uani 1 1 d . . .
H9 H 0.2067 0.4910 1.2063 0.056 Uiso 1 1 calc R . .
C10 C 0.09606(10) 0.44193(9) 1.1168(3) 0.0448(4) Uani 1 1 d . . .
H10 H 0.0724 0.4805 1.1827 0.054 Uiso 1 1 calc R . .
C11 C 0.05066(10) 0.37985(9) 1.0065(2) 0.0383(4) Uani 1 1 d . . .
H11 H -0.0043 0.3765 0.9948 0.046 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 115.73(12) . . ?
N1 C2 O1 122.51(13) . . ?
N1 C2 C2 123.08(8) . 2_556 ?
O1 C2 C2 114.41(8) . 2_556 ?
C2 N1 C3 115.92(12) . . ?
N2 C3 N1 116.99(13) . . ?
N2 C3 C3 122.01(8) . 2_556 ?
N1 C3 C3 120.99(8) . 2_556 ?
C3 N2 C4 115.72(12) . . ?
N2 C4 N3 116.99(12) . . ?
N2 C4 C4 122.22(8) . 2_556 ?
N3 C4 C4 120.74(8) . 2_556 ?
C5 N3 C4 118.15(12) . . ?
N3 C5 C5 120.77(8) . 2_556 ?
N3 C5 C6 115.36(13) . . ?
C5 C5 C6 123.79(8) 2_556 . ?
C11 C6 C7 119.00(14) . . ?
C11 C6 C5 121.68(13) . . ?
C7 C6 C5 118.95(13) . . ?
C8 C7 C6 120.77(14) . . ?
C9 C8 C7 119.50(16) . . ?
C8 C9 C10 120.30(15) . . ?
C11 C10 C9 120.24(16) . . ?
C10 C11 C6 120.17(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4380(19) . ?
O1 C2 1.3283(16) . ?
C2 N1 1.2890(18) . ?
C2 C2 1.459(3) 2_556 ?
N1 C3 1.3781(18) . ?
C3 N2 1.3248(18) . ?
C3 C3 1.447(3) 2_556 ?
N2 C4 1.3443(17) . ?
C4 N3 1.3621(17) . ?
C4 C4 1.418(3) 2_556 ?
N3 C5 1.3163(18) . ?
C5 C5 1.463(3) 2_556 ?
C5 C6 1.4838(19) . ?
C6 C11 1.391(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.388(2) . ?
C8 C9 1.381(2) . ?
C9 C10 1.386(2) . ?
C10 C11 1.384(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 N1 -7.43(19) . . . . ?
C1 O1 C2 C2 172.88(15) . . . 2_556 ?
O1 C2 N1 C3 180.00(12) . . . . ?
C2 C2 N1 C3 -0.3(2) 2_556 . . . ?
C2 N1 C3 N2 178.57(12) . . . . ?
C2 N1 C3 C3 -0.6(2) . . . 2_556 ?
N1 C3 N2 C4 179.39(12) . . . . ?
C3 C3 N2 C4 -1.4(2) 2_556 . . . ?
C3 N2 C4 N3 176.47(12) . . . . ?
C3 N2 C4 C4 -1.1(2) . . . 2_556 ?
N2 C4 N3 C5 178.99(12) . . . . ?
C4 C4 N3 C5 -3.4(2) 2_556 . . . ?
C4 N3 C5 C5 -4.1(2) . . . 2_556 ?
C4 N3 C5 C6 172.78(12) . . . . ?
N3 C5 C6 C11 -133.17(15) . . . . ?
C5 C5 C6 C11 43.6(2) 2_556 . . . ?
N3 C5 C6 C7 39.76(19) . . . . ?
C5 C5 C6 C7 -143.45(17) 2_556 . . . ?
C11 C6 C7 C8 -0.5(2) . . . . ?
C5 C6 C7 C8 -173.63(14) . . . . ?
C6 C7 C8 C9 1.3(2) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C6 1.2(3) . . . . ?
C7 C6 C11 C10 -0.7(2) . . . . ?
C5 C6 C11 C10 172.18(15) . . . . ?
