#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:18:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178429 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/50/4025084.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_4025084
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         'C24 H12 N10, 2(C4 H8 O)'
_chemical_formula_sum            'C32 H28 N10 O2'
_chemical_formula_weight         584.64
_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                 108.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.414(3)
_cell_length_b                   24.064(5)
_cell_length_c                   7.5344(15)
_cell_measurement_reflns_used    2136
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      1.56
_cell_volume                     2817.7(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker APEX CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11372
_diffrn_reflns_theta_full        27.13
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1, Sheldrick, G.M., (2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224.0
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0538
_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)+(0.0961P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1667
_reflns_number_gt                1774
_reflns_number_total             2896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901832n_si_005.cif
_cod_data_source_block           ph2tri
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4025084
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
N2 N 0.08037(13) 0.18845(8) 0.7309(3) 0.0275(5) Uani 1 1 d . . .
N1 N 0.08326(12) 0.28524(7) 0.7396(3) 0.0253(5) Uani 1 1 d . . .
N3 N 0.08173(12) 0.09327(7) 0.7201(3) 0.0269(5) Uani 1 1 d . . .
C4 C 0.04256(15) 0.13915(9) 0.7370(3) 0.0245(5) Uani 1 1 d . . .
C5 C 0.04173(14) 0.23870(9) 0.7432(3) 0.0247(5) Uani 1 1 d . . .
N4 N 0.07959(12) -0.00217(8) 0.7140(3) 0.0282(5) Uani 1 1 d . . .
C6 C 0.04234(14) 0.33380(9) 0.7453(3) 0.0237(5) Uani 1 1 d . . .
C7 C 0.09330(15) 0.38439(9) 0.7401(3) 0.0248(5) Uani 1 1 d . . .
C3 C 0.04106(14) 0.04503(9) 0.7332(3) 0.0243(5) Uani 1 1 d . . .
C2 C 0.03929(15) -0.04923(9) 0.7324(3) 0.0279(6) Uani 1 1 d . . .
C11 C 0.11212(17) 0.47124(9) 0.5995(4) 0.0348(6) Uani 1 1 d . . .
H11 H 0.0905 0.4987 0.5098 0.042 Uiso 1 1 calc R . .
C1 C 0.07724(16) -0.10137(10) 0.7083(4) 0.0317(6) Uani 1 1 d . . .
C8 C 0.17789(15) 0.38845(9) 0.8589(3) 0.0281(6) Uani 1 1 d . . .
H8 H 0.2011 0.3601 0.9439 0.034 Uiso 1 1 calc R . .
C12 C 0.06099(16) 0.42666(9) 0.6108(3) 0.0285(6) Uani 1 1 d . . .
H12 H 0.0044 0.4249 0.5312 0.034 Uiso 1 1 calc R . .
C9 C 0.22748(16) 0.43399(10) 0.8521(4) 0.0340(6) Uani 1 1 d . . .
H9 H 0.2830 0.4370 0.9362 0.041 Uiso 1 1 calc R . .
N5 N 0.10354(15) -0.14349(9) 0.6831(4) 0.0467(7) Uani 1 1 d . . .
C10 C 0.19526(17) 0.47509(10) 0.7209(4) 0.0362(7) Uani 1 1 d . . .
H10 H 0.2294 0.5053 0.7143 0.043 Uiso 1 1 calc R . .
C20 C 0.21625(17) 0.35340(11) 1.3649(4) 0.0394(7) Uani 1 1 d . . .
H20A H 0.2303 0.3890 1.3218 0.047 Uiso 1 1 calc R . .
H20B H 0.2322 0.3542 1.5005 0.047 Uiso 1 1 calc R . .
C22 C 0.20217(16) 0.26344(10) 1.2361(4) 0.0348(6) Uani 1 1 d . . .
H22A H 0.2262 0.2295 1.3015 0.042 Uiso 1 1 calc R . .
H22B H 0.1918 0.2581 1.1030 0.042 Uiso 1 1 calc R . .
C21 C 0.12008(17) 0.27836(12) 1.2723(4) 0.0452(7) Uani 1 1 d . . .
H21A H 0.0704 0.2650 1.1724 0.054 Uiso 1 1 calc R . .
H21B H 0.1189 0.2631 1.3906 0.054 Uiso 1 1 calc R . .
C23 C 0.12221(17) 0.34079(12) 1.2779(4) 0.0468(8) Uani 1 1 d . . .
H23A H 0.0892 0.3552 1.3540 0.056 Uiso 1 1 calc R . .
H23B H 0.0998 0.3564 1.1528 0.056 Uiso 1 1 calc R . .
H2 H 0.134(2) 0.1893(11) 0.722(4) 0.057(9) Uiso 1 1 d . . .
O1 O 0.25980(11) 0.30918(7) 1.3049(3) 0.0440(5) Uani 1 1 d . . .
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
C4 N2 C5 122.8(2) . . ?
C5 N1 C6 117.9(2) . . ?
C4 N3 C3 116.6(2) . . ?
N3 C4 N2 119.7(2) . . ?
N3 C4 C4 122.13(13) . 2_556 ?
N2 C4 C4 118.17(13) . 2_556 ?
N1 C5 N2 119.4(2) . . ?
N1 C5 C5 121.65(13) . 2_556 ?
N2 C5 C5 118.92(13) . 2_556 ?
C3 N4 C2 116.2(2) . . ?
N1 C6 C6 120.44(12) . 2_556 ?
N1 C6 C7 114.64(19) . . ?
C6 C6 C7 124.92(12) 2_556 . ?
C12 C7 C8 118.4(2) . . ?
C12 C7 C6 121.8(2) . . ?
C8 C7 C6 119.6(2) . . ?
N4 C3 N3 117.4(2) . . ?
N4 C3 C3 121.36(13) . 2_556 ?
N3 C3 C3 121.28(12) . 2_556 ?
N4 C2 C2 122.39(13) . 2_556 ?
N4 C2 C1 118.4(2) . . ?
C2 C2 C1 119.18(13) 2_556 . ?
C12 C11 C10 120.1(2) . . ?
N5 C1 C2 176.6(3) . . ?
C9 C8 C7 120.7(2) . . ?
C11 C12 C7 120.6(2) . . ?
C8 C9 C10 120.2(2) . . ?
C9 C10 C11 119.8(2) . . ?
O1 C20 C23 105.0(2) . . ?
O1 C22 C21 106.1(2) . . ?
C23 C21 C22 103.3(2) . . ?
C21 C23 C20 103.1(2) . . ?
C20 O1 C22 110.21(19) . . ?
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
N2 C4 1.346(3) . ?
N2 C5 1.382(3) . ?
N1 C5 1.316(3) . ?
N1 C6 1.355(3) . ?
N3 C4 1.304(3) . ?
N3 C3 1.358(3) . ?
C4 C4 1.472(5) 2_556 ?
C5 C5 1.406(5) 2_556 ?
N4 C3 1.331(3) . ?
N4 C2 1.341(3) . ?
C6 C6 1.414(4) 2_556 ?
C6 C7 1.485(3) . ?
C7 C12 1.390(3) . ?
C7 C8 1.392(3) . ?
C3 C3 1.449(5) 2_556 ?
C2 C2 1.398(5) 2_556 ?
C2 C1 1.438(3) . ?
C11 C12 1.382(3) . ?
C11 C10 1.380(4) . ?
C1 N5 1.141(3) . ?
C8 C9 1.376(3) . ?
C9 C10 1.377(4) . ?
C20 O1 1.434(3) . ?
C20 C23 1.501(4) . ?
C22 O1 1.435(3) . ?
C22 C21 1.502(4) . ?
C21 C23 1.503(4) . ?
