#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/49/2224995.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_2224995
loop_
_publ_author_name
'Jian, Fang-Fang'
'Ren, Ping'
_publ_section_title
;
 5,6-Diphenyl-3-(3-pyridyl)-1,2,4-triazine
;
_journal_coeditor_code           HG2609
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o427
_journal_paper_doi               10.1107/S1600536810002187
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H14 N4'
_chemical_formula_moiety         'C20 H14 N4'
_chemical_formula_sum            'C20 H14 N4'
_chemical_formula_weight         310.35
_chemical_melting_point          444
_chemical_name_common            5,6-Diphenyl-3-(3-pyridyl)-1,2,4-triazine
_chemical_name_systematic
;
5,6-Diphenyl-3-(3-pyridyl)-1,2,4-triazine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 125.587(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4775(16)
_cell_length_b                   7.0923(8)
_cell_length_c                   18.5786(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      1.73
_cell_volume                     1551.3(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4 diffractometer'
_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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9802
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.153
_refine_ls_extinction_coef       0.0105(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0476
_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)+(0.0536P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2184
_reflns_number_total             3770
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2609.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      'P 21/c'
_cod_database_code               2224995
_cod_database_fobs_code          2224995
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
N N1 0.40833(10) 0.74465(17) 0.84881(7) 0.0422(3) Uani d . 1 . .
N N2 0.48148(11) 0.5785(2) 0.75648(8) 0.0554(4) Uani d . 1 . .
N N3 0.55312(11) 0.5984(2) 0.84483(8) 0.0546(4) Uani d . 1 . .
C C20 0.69841(13) 0.6021(2) 1.03161(9) 0.0505(4) Uani d . 1 . .
H H20A 0.7215 0.5456 0.9993 0.061 Uiso calc R 1 . .
C C1 0.19450(14) 0.9625(2) 0.65096(9) 0.0512(4) Uani d . 1 . .
H H1B 0.2415 0.9897 0.6334 0.061 Uiso calc R 1 . .
C C2 0.09076(15) 1.0535(2) 0.61123(10) 0.0598(5) Uani d . 1 . .
H H2B 0.0688 1.1431 0.5674 0.072 Uiso calc R 1 . .
C C3 0.02025(14) 1.0123(3) 0.63613(10) 0.0608(5) Uani d . 1 . .
H H3B -0.0496 1.0727 0.6087 0.073 Uiso calc R 1 . .
C C4 0.05291(13) 0.8823(2) 0.70138(10) 0.0555(4) Uani d . 1 . .
H H4B 0.0050 0.8541 0.7180 0.067 Uiso calc R 1 . .
C C5 0.15676(12) 0.7931(2) 0.74260(9) 0.0475(4) Uani d . 1 . .
H H5A 0.1793 0.7073 0.7879 0.057 Uiso calc R 1 . .
C C6 0.22752(12) 0.8308(2) 0.71683(9) 0.0410(4) Uani d . 1 . .
C C7 0.33957(11) 0.7350(2) 0.76126(8) 0.0398(4) Uani d . 1 . .
C C8 0.37453(12) 0.6390(2) 0.71427(9) 0.0430(4) Uani d . 1 . .
C C9 0.29850(13) 0.5980(2) 0.61817(9) 0.0437(4) Uani d . 1 . .
C C10 0.19430(15) 0.5132(3) 0.58174(10) 0.0625(5) Uani d . 1 . .
H H10A 0.1710 0.4833 0.6176 0.075 Uiso calc R 1 . .
C C11 0.12424(16) 0.4725(3) 0.49224(11) 0.0692(5) Uani d . 1 . .
H H11A 0.0546 0.4141 0.4684 0.083 Uiso calc R 1 . .
C C12 0.15742(15) 0.5181(2) 0.43853(10) 0.0581(5) Uani d . 1 . .
H H12A 0.1102 0.4912 0.3783 0.070 Uiso calc R 1 . .
C C13 0.25980(15) 0.6030(2) 0.47375(10) 0.0578(5) Uani d . 1 . .
H H13A 0.2819 0.6354 0.4373 0.069 Uiso calc R 1 . .
C C14 0.33114(14) 0.6412(2) 0.56364(10) 0.0531(4) Uani d . 1 . .
H H14A 0.4016 0.6964 0.5874 0.064 Uiso calc R 1 . .
C C15 0.51278(12) 0.6718(2) 0.88740(9) 0.0410(4) Uani d . 1 . .
C C16 0.59002(12) 0.6778(2) 0.98515(9) 0.0400(4) Uani d . 1 . .
C C17 0.55691(13) 0.7604(2) 1.03439(9) 0.0506(4) Uani d . 1 . .
H H17A 0.4845 0.8112 1.0062 0.061 Uiso calc R 1 . .
C C18 0.63165(14) 0.7668(2) 1.12525(10) 0.0569(5) Uani d . 1 . .
H H18A 0.6111 0.8231 1.1592 0.068 Uiso calc R 1 . .
C C19 0.73715(14) 0.6882(2) 1.16431(10) 0.0575(5) Uani d . 1 . .
H H19A 0.7876 0.6932 1.2257 0.069 Uiso calc R 1 . .
N N4 0.77171(11) 0.6048(2) 1.11941(8) 0.0585(4) Uani d . 1 . .
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
_geom_angle_publ_flag
C7 N1 C15 . . 116.31(12) ?
C8 N2 N3 . . 119.33(12) ?
C15 N3 N2 . . 118.20(13) ?
N4 C20 C16 . . 124.33(15) ?
N4 C20 H20A . . 117.8 ?
C16 C20 H20A . . 117.8 ?
C6 C1 C2 . . 119.60(16) ?
C6 C1 H1B . . 120.2 ?
C2 C1 H1B . . 120.2 ?
C3 C2 C1 . . 120.50(16) ?
C3 C2 H2B . . 119.8 ?
C1 C2 H2B . . 119.8 ?
C4 C3 C2 . . 119.95(16) ?
C4 C3 H3B . . 120.0 ?
C2 C3 H3B . . 120.0 ?
C3 C4 C5 . . 120.19(16) ?
C3 C4 H4B . . 119.9 ?
C5 C4 H4B . . 119.9 ?
C4 C5 C6 . . 120.33(15) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
C1 C6 C5 . . 119.42(14) ?
C1 C6 C7 . . 120.15(13) ?
C5 C6 C7 . . 120.41(13) ?
N1 C7 C8 . . 120.00(13) ?
N1 C7 C6 . . 117.05(12) ?
C8 C7 C6 . . 122.95(12) ?
N2 C8 C7 . . 120.14(13) ?
N2 C8 C9 . . 116.00(13) ?
C7 C8 C9 . . 123.86(13) ?
C14 C9 C10 . . 118.71(14) ?
C14 C9 C8 . . 120.64(14) ?
C10 C9 C8 . . 120.64(13) ?
C9 C10 C11 . . 120.51(15) ?
C9 C10 H10A . . 119.7 ?
C11 C10 H10A . . 119.7 ?
C12 C11 C10 . . 120.12(17) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
C13 C12 C11 . . 119.82(15) ?
C13 C12 H12A . . 120.1 ?
C11 C12 H12A . . 120.1 ?
C12 C13 C14 . . 120.27(15) ?
C12 C13 H13A . . 119.9 ?
C14 C13 H13A . . 119.9 ?
C9 C14 C13 . . 120.54(16) ?
C9 C14 H14A . . 119.7 ?
C13 C14 H14A . . 119.7 ?
N3 C15 N1 . . 125.41(13) ?
N3 C15 C16 . . 117.45(13) ?
N1 C15 C16 . . 117.13(12) ?
C20 C16 C17 . . 117.00(13) ?
C20 C16 C15 . . 121.79(13) ?
C17 C16 C15 . . 121.21(13) ?
C18 C17 C16 . . 119.76(15) ?
C18 C17 H17A . . 120.1 ?
C16 C17 H17A . . 120.1 ?
C19 C18 C17 . . 118.28(15) ?
C19 C18 H18A . . 120.9 ?
C17 C18 H18A . . 120.9 ?
N4 C19 C18 . . 123.81(15) ?
N4 C19 H19A . . 118.1 ?
C18 C19 H19A . . 118.1 ?
C20 N4 C19 . . 116.80(14) ?
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 C7 . 1.3253(16) ?
N1 C15 . 1.3440(18) ?
N2 C8 . 1.3356(19) ?
N2 N3 . 1.3448(17) ?
N3 C15 . 1.3322(18) ?
C20 N4 . 1.3313(18) ?
C20 C16 . 1.385(2) ?
C20 H20A . 0.9300 ?
C1 C6 . 1.385(2) ?
C1 C2 . 1.388(2) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.375(2) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.370(2) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.381(2) ?
C4 H4B . 0.9300 ?
C5 C6 . 1.386(2) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.4887(19) ?
C7 C8 . 1.4126(19) ?
C8 C9 . 1.4823(19) ?
C9 C14 . 1.379(2) ?
C9 C10 . 1.381(2) ?
C10 C11 . 1.383(2) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.375(2) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.363(2) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.386(2) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
C15 C16 . 1.4788(19) ?
C16 C17 . 1.386(2) ?
C17 C18 . 1.377(2) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.371(2) ?
C18 H18A . 0.9300 ?
C19 N4 . 1.335(2) ?
C19 H19A . 0.9300 ?
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
C20 H20A N3 . 0.93 2.49 2.824(4) 102
C13 H13A Cg1 2_655 0.93 3.49 3.345(4) 91
C19 H19A Cg2 3_666 0.93 3.67 3.109(4) 121
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4912803
