#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/89/2008937.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_2008937
loop_
_publ_author_name
'S. Shanmuga Sundara Raj'
'Hoong-Kun Fun'
'Dun-ru Zhu'
'Fang-Fang Jian'
'Koulin Zhang'
'Xiao-Zeng You'
_publ_section_title
;
 9-(4H-1,2,4-Triazol-4-ylimino)-4,5-diazafluorene
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1526
_journal_page_last               1528
_journal_paper_doi               10.1107/S0108270199007908
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C13 H8 N6'
_chemical_formula_weight         248.25
_chemical_name_systematic
;
9-(4H-1,2,4-triazol-4-ylimino)-4,5-diazafluorene
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 123.7900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.3040(10)
_cell_length_b                   10.4880(10)
_cell_length_c                   14.2670(10)
_cell_measurement_reflns_used    2725
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.36
_cell_volume                     2276.2(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.054
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7790
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.121
_refine_ls_R_factor_gt           0.063
_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/[σ²(Fo²)+(0.1040P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.197
_reflns_number_gt                1553
_reflns_number_total             2817
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1425.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2008937
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.28719(12) 0.54676(19) 0.01741(18) 0.0543(6) Uani d . 1 . . N
N2 0.16892(15) 0.4553(2) -0.0141(2) 0.0737(7) Uani d . 1 . . N
N3 0.18406(14) 0.4119(2) -0.0933(2) 0.0696(7) Uani d . 1 . . N
N4 0.35391(13) 0.6396(2) 0.05776(19) 0.0597(6) Uani d . 1 . . N
N5 0.65616(12) 0.67890(19) 0.19482(18) 0.0540(6) Uani d . 1 . . N
N6 0.61828(13) 0.39625(19) 0.17843(18) 0.0562(5) Uani d . 1 . . N
C1 0.23120(17) 0.5360(3) 0.0496(3) 0.0686(8) Uani d . 1 . . C
H1A 0.2363 0.5802 0.1095 0.082 Uiso calc R 1 . . H
C2 0.25431(17) 0.4680(3) -0.0724(2) 0.0676(8) Uani d . 1 . . C
H2A 0.2791 0.4559 -0.1137 0.081 Uiso calc R 1 . . H
C3 0.43059(14) 0.5982(2) 0.0917(2) 0.0490(6) Uani d . 1 . . C
C4 0.50250(15) 0.6913(2) 0.1266(2) 0.0519(6) Uani d . 1 . . C
C5 0.50356(18) 0.8223(3) 0.1285(3) 0.0735(9) Uani d . 1 . . C
H5A 0.4536 0.8697 0.1070 0.088 Uiso calc R 1 . . H
C6 0.58326(19) 0.8796(3) 0.1644(3) 0.0820(9) Uani d . 1 . . C
H6A 0.5877 0.9680 0.1674 0.098 Uiso calc R 1 . . H
C7 0.65583(18) 0.8064(2) 0.1957(3) 0.0681(8) Uani d . 1 . . C
H7A 0.7081 0.8483 0.2190 0.082 Uiso calc R 1 . . H
C8 0.57854(14) 0.6259(2) 0.15952(19) 0.0477(6) Uani d . 1 . . C
C9 0.55991(14) 0.4876(2) 0.15069(19) 0.0458(6) Uani d . 1 . . C
C10 0.58666(18) 0.2771(3) 0.1672(3) 0.0689(8) Uani d . 1 . . C
H10A 0.6252 0.2093 0.1862 0.083 Uiso calc R 1 . . H
C11 0.50092(18) 0.2493(2) 0.1295(3) 0.0676(8) Uani d . 1 . . C
H11A 0.4835 0.1649 0.1243 0.081 Uiso calc R 1 . . H
C12 0.44105(16) 0.3457(2) 0.0995(2) 0.0558(7) Uani d . 1 . . C
H12A 0.3830 0.3282 0.0738 0.067 Uiso calc R 1 . . H
C13 0.47020(15) 0.4696(2) 0.10895(19) 0.0462(6) Uani d . 1 . . C
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
_geom_angle_publ_flag
C1 N1 C2 104.5(2) y
C1 N1 N4 124.9(2) y
C2 N1 N4 129.5(2) y
C1 N2 N3 106.9(2) ?
C2 N3 N2 106.8(2) ?
C3 N4 N1 116.0(2) y
C8 N5 C7 114.2(2) ?
C9 N6 C10 114.5(2) ?
N2 C1 N1 110.8(2) ?
N3 C2 N1 111.0(2) ?
N4 C3 C4 119.0(2) ?
N4 C3 C13 134.6(2) y
C4 C3 C13 106.35(18) ?
C5 C4 C8 119.4(2) ?
C5 C4 C3 131.6(2) ?
C8 C4 C3 109.0(2) ?
C4 C5 C6 116.2(3) ?
C7 C6 C5 120.3(3) ?
N5 C7 C6 124.3(2) ?
N5 C8 C4 125.6(2) ?
N5 C8 C9 125.9(2) ?
C4 C8 C9 108.50(18) ?
N6 C9 C13 125.8(2) ?
N6 C9 C8 125.15(19) ?
C13 C9 C8 109.00(19) ?
N6 C10 C11 124.2(3) ?
C12 C11 C10 120.3(2) ?
C11 C12 C13 117.6(2) ?
C12 C13 C9 117.5(2) ?
C12 C13 C3 135.3(2) ?
C9 C13 C3 107.10(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.341(3) y
N1 C2 . 1.353(3) y
N1 N4 . 1.410(3) y
N2 C1 . 1.299(3) y
N2 N3 . 1.381(3) y
N3 C2 . 1.289(3) y
N4 C3 . 1.280(3) y
N5 C8 . 1.336(3) y
N5 C7 . 1.337(3) y
N6 C9 . 1.321(3) y
N6 C10 . 1.349(3) y
C3 C4 . 1.485(3) ?
C3 C13 . 1.485(3) ?
C4 C5 . 1.374(4) ?
C4 C8 . 1.378(3) ?
C5 C6 . 1.386(4) ?
C6 C7 . 1.376(4) ?
C8 C9 . 1.479(3) ?
C9 C13 . 1.414(3) ?
C10 C11 . 1.378(4) ?
C11 C12 . 1.372(3) ?
C12 C13 . 1.383(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1A N5 2_655 0.93 2.57 3.381(4) 145 yes
C2 H2A N5 5_665 0.93 2.50 3.361(4) 153 yes
C5 H5A N2 7_565 0.93 2.62 3.513(4) 162 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4421846
