data_2013845
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o57
_journal_page_last  o59
_publ_section_title
;
Hydrogen-bonding patterns in two structural isomers of
3,6-bis(2-chlorophenyl)-1,4-dihydro-1,2,4,5-tetrazine
;
loop_
_publ_author_name
  'Zachara, Janusz'
  'Madura, Izabela'
  'W\/lostowski, Marek'
_chemical_formula_moiety  'C14 H10 Cl2 N4'
_chemical_formula_sum  'C14 H10 Cl2 N4'
_chemical_formula_structural  'C2 H2 N4( C6H4Cl)2'
_chemical_formula_iupac  'C14 H10 Cl2 N4'
_chemical_formula_weight  305.16
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
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'
_cell_length_a  16.0020(12)
_cell_length_b  9.4123(8)
_cell_length_c  10.5752(7)
_cell_angle_alpha  90.00
_cell_angle_beta  121.664(5)
_cell_angle_gamma  90.00
_cell_volume  1355.69(18)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.495
_diffrn_ambient_temperature  293(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
  Cl1 0.16401(5) 0.74870(6) 0.21918(8) 0.0646(3) Uani d . 1 . . Cl
  N1 0.04530(12) 0.4499(2) 0.18150(18) 0.0376(4) Uani d . 1 . . N
  N2 0.05456(12) 0.49908(19) 0.40415(17) 0.0372(4) Uani d . 1 . . N
  C1 0.20247(14) 0.5248(2) 0.4027(2) 0.0359(5) Uani d . 1 . . C
  C2 0.24122(16) 0.6321(2) 0.3587(2) 0.0439(5) Uani d . 1 . . C
  C3 0.3429(2) 0.6493(3) 0.4296(3) 0.0618(8) Uani d . 1 . . C
  C4 0.4044(2) 0.5597(4) 0.5428(3) 0.0646(8) Uani d . 1 . . C
  C5 0.36748(18) 0.4549(3) 0.5887(3) 0.0589(7) Uani d . 1 . . C
  C6 0.26745(15) 0.4384(3) 0.5202(2) 0.0434(5) Uani d . 1 . . C
  C10 0.09617(14) 0.4949(2) 0.3295(2) 0.0334(5) Uani d . 1 . . C
  H1 0.0749(15) 0.470(2) 0.134(2) 0.036(5) Uiso d . 1 . . H
  H3 0.362(2) 0.720(3) 0.398(3) 0.072(9) Uiso d . 1 . . H
  H4 0.475(2) 0.568(4) 0.593(3) 0.094(10) Uiso d . 1 . . H
  H5 0.412(2) 0.391(3) 0.670(3) 0.078(9) Uiso d . 1 . . H
  H6 0.2407(16) 0.363(3) 0.552(2) 0.049(6) Uiso d . 1 . . H
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
  Cl1 0.0958(6) 0.0467(4) 0.0745(5) 0.0089(3) 0.0608(4) 0.0122(3)
  N1 0.0339(9) 0.0530(11) 0.0309(9) 0.0034(8) 0.0204(8) -0.0022(8)
  N2 0.0340(9) 0.0513(10) 0.0298(8) -0.0032(7) 0.0191(7) 0.0000(7)
  C1 0.0388(11) 0.0407(11) 0.0350(10) -0.0041(9) 0.0242(9) -0.0080(8)
  C2 0.0558(13) 0.0434(12) 0.0480(12) -0.0080(10) 0.0380(11) -0.0100(10)
  C3 0.0720(18) 0.0631(16) 0.0756(18) -0.0309(15) 0.0560(16) -0.0241(15)
  C4 0.0409(14) 0.091(2) 0.0577(16) -0.0135(14) 0.0232(13) -0.0206(15)
  C5 0.0424(13) 0.0792(19) 0.0461(13) -0.0030(13) 0.0172(11) -0.0095(13)
  C6 0.0378(12) 0.0531(14) 0.0372(11) -0.0024(10) 0.0181(10) -0.0040(10)
  C10 0.0370(11) 0.0366(10) 0.0309(10) -0.0004(8) 0.0208(9) 0.0004(8)
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
  Cl1 C2 . 1.730(2) yes
  N1 C10 . 1.398(2) yes
  N1 N2 2 1.438(2) yes
  N1 H1 . 0.88(2) no
  N2 C10 . 1.273(2) yes
  N2 N1 2 1.438(2) no
  C10 C1 . 1.480(3) yes
  C1 C2 . 1.388(3) no
  C1 C6 . 1.389(3) no
  C2 C3 . 1.399(3) no
  C3 C4 . 1.369(4) no
  C3 H3 . 0.87(3) no
  C4 C5 . 1.363(4) no
  C4 H4 . 0.97(3) no
  C5 C6 . 1.376(3) no
  C5 H5 . 0.98(3) no
  C6 H6 . 0.98(2) no