#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/30/2233054.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233054
loop_
_publ_author_name
'Yang, Wei'
'Qiu, Qi-Ming'
'Zhou, Li-Li'
'Jin, Qiong-Hua'
'Zhang, Cun-Lin'
_publ_section_title
;
 An orthorhombic polymorph of
 pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile
;
_journal_coeditor_code           ZQ2127
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3250
_journal_page_last               o3251
_journal_paper_doi               10.1107/S1600536811047039
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H6 N6'
_chemical_formula_moiety         'C16 H6 N6'
_chemical_formula_sum            'C16 H6 N6'
_chemical_formula_weight         282.27
_chemical_name_common
;
1,4,8,9-tetraazatriphenylene-2,3-dicarbonitrile
;
_chemical_name_systematic
;
pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1055(13)
_cell_length_b                   16.3331(14)
_cell_length_c                   5.2694(4)
_cell_measurement_reflns_used    1184
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.483
_cell_measurement_theta_min      2.888
_cell_volume                     1214.00(18)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics
;SHELXTL (Sheldrick, 2008) and
ORTEPIII (Burnett & Johnson, 1996)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4543
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0556P)²+0.3018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                759
_reflns_number_total             1113
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zq2127.cif
_cod_data_source_block           I
_cod_database_code               2233054
_cod_database_fobs_code          2233054
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.56932(11) 0.33317(10) -0.1078(3) 0.0347(5) Uani d . 1 1
N N2 0.77953(11) 0.33585(9) 0.6140(3) 0.0322(4) Uani d . 1 1
N N3 0.92249(13) 0.37680(13) 1.1146(4) 0.0539(6) Uani d . 1 1
C C1 0.61818(12) 0.29508(11) 0.0786(3) 0.0279(5) Uani d . 1 1
C C2 0.67134(12) 0.33802(11) 0.2603(3) 0.0281(5) Uani d . 1 1
C C3 0.67273(13) 0.42373(12) 0.2476(4) 0.0349(5) Uani d . 1 1
H H3 0.7060 0.4542 0.3673 0.042 Uiso calc R 1 1
C C4 0.62440(14) 0.46176(13) 0.0564(4) 0.0381(6) Uani d . 1 1
H H4 0.6249 0.5185 0.0422 0.046 Uiso calc R 1 1
C C5 0.57451(13) 0.41428(12) -0.1161(4) 0.0369(5) Uani d . 1 1
H H5 0.5426 0.4410 -0.2463 0.044 Uiso calc R 1 1
C C6 0.72648(12) 0.29328(11) 0.4470(3) 0.0285(5) Uani d . 1 1
C C7 0.83106(12) 0.29288(12) 0.7773(4) 0.0317(5) Uani d . 1 1
C C8 0.88437(14) 0.33918(13) 0.9640(4) 0.0372(5) Uani d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0333(9) 0.0368(10) 0.0339(10) 0.0021(7) -0.0025(8) 0.0040(8)
N2 0.0305(9) 0.0357(9) 0.0303(9) -0.0020(7) 0.0014(8) -0.0007(8)
N3 0.0476(11) 0.0703(14) 0.0437(12) -0.0084(10) -0.0041(10) -0.0142(11)
C1 0.0249(9) 0.0318(10) 0.0271(11) 0.0011(8) 0.0041(8) 0.0010(9)
C2 0.0255(9) 0.0291(10) 0.0296(11) 0.0002(8) 0.0036(8) 0.0018(9)
C3 0.0335(11) 0.0312(10) 0.0401(13) -0.0031(9) -0.0007(10) -0.0031(10)
C4 0.0353(11) 0.0302(10) 0.0488(14) 0.0018(9) 0.0026(11) 0.0059(10)
C5 0.0354(11) 0.0370(12) 0.0382(12) 0.0052(9) -0.0005(10) 0.0082(10)
C6 0.0253(9) 0.0319(9) 0.0283(10) -0.0016(8) 0.0028(8) -0.0029(8)
C7 0.0264(10) 0.0428(11) 0.0261(11) -0.0027(8) 0.0008(9) -0.0014(9)
C8 0.0314(11) 0.0480(13) 0.0321(12) -0.0018(9) 0.0013(10) -0.0013(11)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C5 N1 C1 . . 117.07(17)
C7 N2 C6 . . 117.02(16)
N1 C1 C2 . . 122.55(17)
N1 C1 C1 . 7_565 117.41(10)
C2 C1 C1 . 7_565 119.97(11)
C3 C2 C1 . . 118.29(17)
C3 C2 C6 . . 121.85(17)
C1 C2 C6 . . 119.80(17)
C4 C3 C2 . . 118.85(18)
C4 C3 H3 . . 120.6
C2 C3 H3 . . 120.6
C3 C4 C5 . . 118.85(18)
C3 C4 H4 . . 120.6
C5 C4 H4 . . 120.6
N1 C5 C4 . . 124.37(19)
N1 C5 H5 . . 117.8
C4 C5 H5 . . 117.8
N2 C6 C6 . 7_565 121.05(10)
N2 C6 C2 . . 118.69(16)
C6 C6 C2 7_565 . 120.23(10)
N2 C7 C7 . 7_565 121.93(10)
N2 C7 C8 . . 116.61(17)
C7 C7 C8 7_565 . 121.41(11)
N3 C8 C7 . . 177.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C5 . 1.327(3)
N1 C1 . 1.352(2)
N2 C7 . 1.327(2)
N2 C6 . 1.348(2)
N3 C8 . 1.138(3)
C1 C2 . 1.404(2)
C1 C1 7_565 1.473(4)
C2 C3 . 1.402(3)
C2 C6 . 1.451(2)
C3 C4 . 1.366(3)
C3 H3 . 0.9300
C4 C5 . 1.387(3)
C4 H4 . 0.9300
C5 H5 . 0.9300
C6 C6 7_565 1.414(4)
C7 C7 7_565 1.401(4)
C7 C8 . 1.451(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C5 N1 C1 C2 . . 1.0(3)
C5 N1 C1 C1 . 7_565 -175.87(13)
N1 C1 C2 C3 . . 0.5(3)
C1 C1 C2 C3 7_565 . 177.37(12)
N1 C1 C2 C6 . . -176.57(15)
C1 C1 C2 C6 7_565 . 0.26(19)
C1 C2 C3 C4 . . -1.5(3)
C6 C2 C3 C4 . . 175.52(17)
C2 C3 C4 C5 . . 1.0(3)
C1 N1 C5 C4 . . -1.7(3)
C3 C4 C5 N1 . . 0.7(3)
C7 N2 C6 C6 . 7_565 -0.18(19)
C7 N2 C6 C2 . . -178.16(15)
C3 C2 C6 N2 . . 0.7(3)
C1 C2 C6 N2 . . 177.73(15)
C3 C2 C6 C6 . 7_565 -177.26(13)
C1 C2 C6 C6 . 7_565 -0.26(19)
C6 N2 C7 C7 . 7_565 0.18(19)
C6 N2 C7 C8 . . -177.14(15)
