data_2200559
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o839
_journal_page_last  o841
_publ_section_title
;
Zigzag hydrogen-bonded sheets in the structure of p-phenylazoaniline
hydrochloride
;
loop_
_publ_author_name
  'Mahmoudkhani, Amir H.'
  'Langer, Vratislav'
_chemical_formula_moiety  'C12 H12 N3 1+, Cl 1-'
_chemical_formula_sum  'C12 H12 Cl N3'
_chemical_formula_iupac  'C12 H12 N3 1+, Cl 1-'
_chemical_formula_weight  233.70
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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'
_cell_length_a  7.3718(3)
_cell_length_b  18.5164(7)
_cell_length_c  8.91230(10)
_cell_angle_alpha  90.00
_cell_angle_beta  111.9130(10)
_cell_angle_gamma  90.00
_cell_volume  1128.63(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  297(2)
_exptl_crystal_density_diffrn  1.375
_diffrn_ambient_temperature  297(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
  Cl  .25125(11)  .35094(3)  .25208(7)  .0583(3) Uani d . 1 . . Cl
  N1  -.1796(3)  .69262(11)  .1163(3)  .0450(5) Uani d D 1 . . N
  H2  -.227(4)  .6825(15)  .013(2)  .058(9) Uiso d D 1 . . H
  H1  -.212(4)  .7331(11)  .151(3)  .055(8) Uiso d D 1 . . H
  N2  .2890(3)  .51264(9)  .5880(2)  .0367(5) Uani d . 1 . . N
  N3  .3509(3)  .44960(10)  .5676(2)  .0363(5) Uani d D 1 . . N
  H3  .322(4)  .4275(13)  .474(2)  .053(8) Uiso d D 1 . . H
  C11  -.0719(3)  .64667(11)  .2278(3)  .0357(6) Uani d . 1 . . C
  C12  -.0222(3)  .57759(12)  .1830(3)  .0384(6) Uani d . 1 . . C
  H12  -.0707  .5641  .0747  .041(7) Uiso calc R 1 . . H
  C13  .0940(3)  .53167(12)  .2955(3)  .0379(6) Uani d . 1 . . C
  H13  .1252  .4870  .2640  .042(6) Uiso calc R 1 . . H
  C14  .1692(3)  .55117(11)  .4622(3)  .0344(5) Uani d . 1 . . C
  C15  .1147(3)  .61907(12)  .5067(3)  .0394(6) Uani d . 1 . . C
  H15  .1603  .6321  .6153  .041(7) Uiso calc R 1 . . H
  C16  -.0026(3)  .66536(12)  .3942(3)  .0386(6) Uani d . 1 . . C
  H16  -.0376  .7093  .4261  .049(7) Uiso calc R 1 . . H
  C21  .4736(3)  .41061(12)  .7048(3)  .0348(5) Uani d . 1 . . C
  C22  .5158(4)  .33944(13)  .6843(3)  .0435(6) Uani d . 1 . . C
  H22  .4691  .3185  .5821  .038(6) Uiso calc R 1 . . H
  C23  .6290(4)  .29977(14)  .8188(3)  .0516(7) Uani d . 1 . . C
  H23  .6572  .2517  .8069  .059(8) Uiso calc R 1 . . H
  C24  .7000(4)  .33110(16)  .9698(3)  .0555(7) Uani d . 1 . . C
  H24  .7746  .3039 1.0594  .078(9) Uiso calc R 1 . . H
  C25  .6609(4)  .40211(16)  .9886(3)  .0562(7) Uani d . 1 . . C
  H25  .7110  .4232 1.0907  .071(9) Uiso calc R 1 . . H
  C26  .5472(4)  .44282(14)  .8565(3)  .0466(6) Uani d . 1 . . C
  H26  .5206  .4910  .8692  .055(8) Uiso calc R 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
  Cl  .0853(6)  .0381(4)  .0381(4)  .0054(3)  .0076(4)  -.0031(2)
  N1  .0482(13)  .0401(12)  .0390(14)  .0084(10)  .0072(10)  .0050(9)
  N2  .0323(11)  .0327(10)  .0384(11)  -.0019(8)  .0055(8)  .0013(8)
  N3  .0349(11)  .0338(10)  .0322(11)  .0011(8)  .0031(9)  .0002(8)
  C11  .0320(12)  .0340(12)  .0394(13)  -.0021(9)  .0114(10)  .0038(9)
  C12  .0398(13)  .0365(12)  .0323(13)  .0010(10)  .0058(10)  -.0017(9)
  C13  .0391(13)  .0321(11)  .0381(14)  .0004(10)  .0096(10)  -.0011(9)
  C14  .0295(12)  .0311(11)  .0358(13)  -.0022(9)  .0042(9)  .0029(9)
  C15  .0442(14)  .0361(12)  .0321(13)  -.0038(10)  .0078(10)  -.0032(9)
  C16  .0400(13)  .0318(11)  .0403(14)  .0014(10)  .0104(11)  -.0018(9)
  C21  .0259(11)  .0374(12)  .0351(13)  .0019(9)  .0046(9)  .0044(9)
  C22  .0391(13)  .0411(13)  .0417(15)  .0018(10)  .0051(11)  -.0003(10)
  C23  .0452(15)  .0427(14)  .0597(18)  .0116(12)  .0112(12)  .0065(12)
  C24  .0503(16)  .0612(17)  .0478(16)  .0202(13)  .0100(13)  .0194(13)
  C25  .0533(17)  .0669(18)  .0365(15)  .0169(14)  .0030(12)  .0010(12)
  C26  .0459(15)  .0473(14)  .0378(14)  .0121(11)  .0056(11)  -.0001(11)
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 C11 . 1.324(3) yes
  N1 H2 .  .878(17) ?
  N1 H1 .  .876(17) ?
  N2 N3 . 1.291(3) yes
  N2 C14 . 1.344(3) yes
  N3 C21 . 1.418(3) yes
  N3 H3 .  .879(16) ?
  C11 C16 . 1.420(3) ?
  C11 C12 . 1.428(3) ?
  C12 C13 . 1.350(3) ?
  C12 H12 .  .9300 ?
  C13 C14 . 1.425(3) ?
  C13 H13 .  .9300 ?
  C14 C15 . 1.421(3) ?
  C15 C16 . 1.356(3) ?
  C15 H15 .  .9300 ?
  C16 H16 .  .9300 ?
  C21 C22 . 1.382(3) ?
  C21 C26 . 1.389(3) ?
  C22 C23 . 1.388(3) ?
  C22 H22 .  .9300 ?
  C23 C24 . 1.377(4) ?
  C23 H23 .  .9300 ?
  C24 C25 . 1.370(4) ?
  C24 H24 .  .9300 ?
  C25 C26 . 1.386(3) ?
  C25 H25 .  .9300 ?
  C26 H26 .  .9300 ?