data_2011478
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1280
_journal_page_last  1281
_publ_section_title
;
2-Hydroxy-5-[(E)-(4-methoxyphenyl)diazenyl]benzoic acid
;
loop_
_publ_author_name
  'Basu Baul, T. S.'
  'Dhar, S.'
  'Tiekink, E. R. T.'
_chemical_formula_moiety  'C14 H12 N2 O4'
_chemical_formula_sum  'C14 H12 N2 O4'
_chemical_formula_weight  272.26
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '1/2+x,1/2-y,  -z'
  '  -x,1/2+y,1/2-z'
  '1/2-x,  -y,1/2+z'
  '  -x,  -y,  -z'
  '1/2-x,1/2+y,  +z'
  '  +x,1/2-y,1/2+z'
  '1/2+x,  +y,1/2-z'
_cell_length_a  24.902(6)
_cell_length_b  15.109(6)
_cell_length_c  6.674(2)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  2511.0(10)
_cell_formula_units_Z  8
_cell_measurement_temperature  173
_exptl_crystal_density_diffrn  1.440
_diffrn_ambient_temperature  173
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_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
  O1  .94177(4)  .01763(7)  .8390(2)  .0300(3) Uani d ? . 1.000
  O2 1.02771(4)  .06121(7)  .82850(10)
  .0288(3) Uani d ? . 1.000
  O3 1.06264(4)  .14755(7)  .5120(2)  .0295(3) Uani d ? . 1.000
  O4  .64850(4)  .11987(8)  -.3216(2)  .0377(3) Uani d ? . 1.000
  N1  .85392(5)  .11762(8)  .2170(2)  .0297(4) Uani d ? . 1.000
  N2  .84935(5)  .14252(8)  .0377(2)  .0297(4) Uani d ? . 1.000
  C1  .98228(6)  .05760(10)
  .7523(2)  .0248(4) Uani d ? . 1.000
  C2  .97032(6)  .09777(9)  .5580(2)  .0227(4) Uani d ? . 1.000
  C3 1.01099(6)  .14092(9)  .4502(2)  .0229(4) Uani d ? . 1.000
  C4  .99862(6)  .18081(9)  .2668(2)  .0269(4) Uani d ? . 1.000
  C5  .94770(6)  .17542(9)  .1891(2)  .0263(4) Uani d ? . 1.000
  C6  .90729(6)  .12980(10)
  .2921(2)  .0254(4) Uani d ? . 1.000
  C7  .91851(6)  .09330(10)
  .4770(2)  .0248(4) Uani d ? . 1.000
  C8  .79720(6)  .13210(10)
  -.0465(2)  .0275(4) Uani d ? . 1.000
  C9  .79165(6)  .16440(10)
  -.2393(2)  .0310(4) Uani d ? . 1.000
  C10  .74264(6)  .16190(10)
  -.3383(2)  .0314(4) Uani d ? . 1.000
  C11  .69877(6)  .12530(10)
  -.2405(2)  .0278(4) Uani d ? . 1.000
  C12  .70427(6)  .09130(10)
  -.0478(3)  .0336(5) Uani d ? . 1.000
  C13  .75293(6)  .09410(10)
  .0491(2)  .0326(4) Uani d ? . 1.000
  C14  .64184(7)  .15240(10)
  -.5209(3)  .0506(6) Uani d ? . 1.000
  H1  .9516  -.0074  .9556  .053 Uiso c ? . 1.000
  H2 1.0645  .1236  .6288  .057 Uiso c ? . 1.000
  H3 1.0262  .2132  .1986  .031 Uiso c ? . 1.000
  H4  .9402  .2035  .0642  .022 Uiso c ? . 1.000
  H5  .8911  .0637  .5487  .027 Uiso c ? . 1.000
  H6  .8219  .1928  -.3032  .046 Uiso c ? . 1.000
  H7  .7397  .1858  -.4756  .037 Uiso c ? . 1.000
  H8  .6744  .0626  .0150  .051 Uiso c ? . 1.000
  H9  .7577  .0695  .1844  .040 Uiso c ? . 1.000
  H10  .6643  .1185  -.6154  .092 Uiso c ? . 1.000
  H11  .6502  .2193  -.5258  .071 Uiso c ? . 1.000
  H12  .6056  .1444  -.5521  .051 Uiso c ? . 1.000
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
  O1  .0274(6)  .0382(6)  .0244(6)  -.0033(5)  -.0005(5)  .0082(5)
  O2  .0253(6)  .0378(6)  .0232(5)  -.0029(5)  -.0038(5)  .0042(5)
  O3  .0224(5)  .0387(7)  .0275(6)  -.0022(5)  -.0023(5)  .0052(5)
  O4  .0250(6)  .0536(7)  .0345(7)  -.0067(6)  -.0060(5)  .0073(6)
  N1  .0266(7)  .0316(7)  .0310(8)  .0005(6)  -.0054(6)  .0029(6)
  N2  .0250(7)  .0346(8)  .0294(7)  .0014(6)  -.0035(6)  .0017(6)
  C1  .0271(8)  .0239(8)  .0233(8)  .0011(6)  .0014(7)  -.0036(7)
  C2  .0248(8)  .0221(7)  .0211(7)  .0027(6)  .0007(6)  -.0011(6)
  C3  .0212(7)  .0233(8)  .0242(8)  .0014(6)  -.0001(6)  -.0034(7)
  C4  .0271(8)  .0267(8)  .0269(8)  -.0016(6)  .0022(7)  .0029(7)
  C5  .0288(8)  .0261(8)  .0238(8)  .0016(6)  -.0016(7)  .0036(7)
  C6  .0229(8)  .0270(8)  .0262(8)  .0018(6)  -.0025(6)  -.0018(7)
  C7  .0238(8)  .0237(8)  .0270(8)  -.0015(6)  .0019(7)  .0001(7)
  C8  .0234(8)  .0306(9)  .0283(8)  .0010(7)  -.0038(7)  -.0007(7)
  C9  .0236(8)  .0400(10)
  .0290(9)  -.0031(7)  .0011(7)  .0037(8)
  C10  .0296(8)  .0390(10)
  .0252(8)  -.0020(7)  -.0021(7)  .0054(8)
  C11  .0241(8)  .0298(8)  .0297(9)  -.0005(6)  -.0043(7)  -.0017(7)
  C12  .0271(9)  .0410(10)
  .0326(9)  -.0094(7)  -.0002(7)  .0057(8)
  C13  .0322(9)  .0370(10)
  .0281(8)  -.0025(7)  -.0028(7)  .0061(8)
  C14  .0330(10)
  .0760(10)
  .0420(10)
  -.0099(9)  -.0152(9)  .0170(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C1 . . 1.311(2) yes
  O1 H1 . .  .90 no
  O2 C1 . . 1.241(2) yes
  O3 C3 . . 1.355(2) yes
  O3 H2 . .  .86 no
  O4 C11 . . 1.367(2) yes
  O4 C14 . . 1.427(3) yes
  N1 N2 . . 1.260(2) yes
  N1 C6 . . 1.432(2) yes
  N2 C8 . . 1.424(2) yes
  C1 C2 . . 1.462(3) no
  C2 C3 . . 1.403(2) no
  C2 C7 . . 1.400(2) no
  C3 C4 . . 1.398(3) no
  C4 C5 . . 1.372(3) no
  C4 H3 . .  .96 no
  C5 C6 . . 1.401(2) no
  C5 H4 . .  .95 no
  C6 C7 . . 1.380(3) no
  C7 H5 . .  .95 no
  C8 C9 . . 1.383(3) no
  C8 C13 . . 1.397(3) no
  C9 C10 . . 1.388(3) no
  C9 H6 . .  .97 no
  C10 C11 . . 1.388(3) no
  C10 H7 . .  .99 no
  C11 C12 . . 1.392(3) no
  C12 C13 . . 1.374(3) no
  C12 H8 . .  .96 no
  C13 H9 . .  .98 no
  C14 H10 . .  .99 no
  C14 H11 . . 1.03 no
  C14 H12 . .  .93 no