data_2006140
_journal_name_full  'Acta Crystallographica'
_journal_year  1997
_journal_volume  C53
_journal_page_first  620
_journal_page_last  624
_publ_section_title
;
(E)-o-Stilbenecarboxylic Acid and its p-Methyl, Chloro and
Methoxy Derivatives
;
loop_
_publ_author_name
 'Hamazaki, Hiroshi'
 'Ohba, Shigeru'
 'Toda, Fumio'
 'Takumi, Hideaki'
_chemical_formula_moiety  'C15 H11 Cl O2'
_chemical_formula_sum  'C15 H11 Cl O2'
_chemical_formula_structural  'C6H4(COOH)(C2H2C6H4Cl)'
_chemical_formula_weight  258.70
_chemical_melting_point  '418-420'
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
 +x,+y,+z
 1/2-x,1/2+y,1/2-z
 -x,-y,-z
 1/2+x,1/2-y,1/2+z
_cell_length_a  12.977(5)
_cell_length_b  8.023(4)
_cell_length_c  25.171(3)
_cell_angle_alpha  90
_cell_angle_beta  103.56(2)
_cell_angle_gamma  90
_cell_volume  2547.6(16)
_cell_formula_units_Z  8
_cell_measurement_temperature  300
_exptl_crystal_density_diffrn  1.349
_diffrn_ambient_temperature  300
_refine_ls_R_factor_obs   .0505
_refine_ls_wR_factor_obs   .0452
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
 O1  -.18060(10)
 .3323(2)  .47934(5)  .0920(10)
   Uij 1.000
 O2  -.04870(10)
 .3894(2)  .54970(5)  .0800(10)
   Uij 1.000
 C3  -.0871(2)  .3212(2)  .50155(8)  .0640(10)
   Uij 1.000
 C4  -.0078(2)  .2286(2)  .47914(7)  .0620(10)
   Uij 1.000
 C5  .0894(2)  .1929(3)  .51363(9)  .0720(10)
  Uij 1.000
 C6  .1648(2)  .1003(3)  .49700(10)
  .0780(10)
 Uij 1.000
 C7  .1436(2)  .0427(3)  .44430(10)
  .0830(10)
 Uij 1.000
 C8  .0495(2)  .0786(3)  .40885(9)  .0800(10)
  Uij 1.000
 C9  -.0305(2)  .1706(2)  .42452(8)  .0660(10)
   Uij 1.000
 C10  -.1301(2)  .2031(3)  .38489(8)  .0780(10)
 Uij 1.000
 C11  -.1673(2)  .1253(3)  .33857(9)  .0810(10)
 Uij 1.000
 C12  -.2687(2)  .1552(2)  .29956(8)  .0720(10)
 Uij 1.000
 C13  -.2878(2)  .0923(3)  .24670(10)
 .0900(10)
   Uij 1.000
 C14  -.3826(2)  .1166(3)  .20970(10)
 .0940(10)
   Uij 1.000
 C15  -.4614(2)  .2025(3)  .22489(8)  .0750(10)
 Uij 1.000
 C16  -.4461(2)  .2679(3)  .27679(9)  .0840(10)
 Uij 1.000
 C17  -.3505(2)  .2439(3)  .31343(9)  .0810(10)
 Uij 1.000
 Cl18  -.58422(5)  .22737(9)  .17966(2)  .1043(3) Uij 1.000
 O101  .20300(10)
  .4481(2)  .41436(5)  .0860(10)
 Uij 1.000
 O102  .32370(10)
  .4823(2)  .49022(6)  .1130(10)
 Uij 1.000
 C103  .2891(2)  .4145(2)  .44224(7)  .0630(10)
 Uij 1.000
 C104  .36600(10)
  .2934(2)  .42851(7)  .0580(10)
 Uij 1.000
 C105  .4613(2)  .2701(3)  .46668(8)  .0740(10)
 Uij 1.000
 C106  .5367(2)  .1609(3)  .45760(10)
 .0880(10)
   Uij 1.000
 C107  .5172(2)  .0701(3)  .41030(10)
 .0900(10)
   Uij 1.000
 C108  .4238(2)  .0895(3)  .37224(9)  .0780(10)
 Uij 1.000
 C109  .34530(10)
  .2012(2)  .37907(7)  .0590(10)
 Uij 1.000
 C110  .2483(2)  .2184(3)  .33622(8)  .0640(10)
 Uij 1.000
 C111  .2326(2)  .1733(3)  .28493(8)  .0710(10)
 Uij 1.000
 C112  .13350(10)
  .1855(2)  .24314(7)  .0610(10)
 Uij 1.000
 C113  .1262(2)  .1188(3)  .19100(8)  .0730(10)
 Uij 1.000
 C114  .0329(2)  .1198(3)  .15210(8)  .0780(10)
 Uij 1.000
 C115  -.0559(2)  .1866(2)  .16420(7)  .0660(10)
  Uij 1.000
 C116  -.0515(2)  .2584(3)  .21414(8)  .0740(10)
  Uij 1.000
 C117  .0424(2)  .2565(3)  .25292(8)  .0760(10)
 Uij 1.000
 Cl118  -.17626(4)  .18053(8)  .11604(2)  .0956(3) Uij 1.000
 H2  -.09719  .46297  .56160  .170(10)
 Uiso 1.000
 H5  .1020(13)  .232(2) .5479(7)  .075(6) Uiso 1.000
 H6  .2272(13)  .076(2) .5236(7)  .072(6) Uiso 1.000
 H7  .1963(14)  -.017(2) .4328(7)  .072(6) Uiso 1.000
 H8  .0335(14)  .035(2) .3706(8)  .095(7) Uiso 1.000
 H10  -.1719(13)  .285(2) .3927(7)  .070(6) Uiso 1.000
 H11  -.1305(15)  .032(3) .3291(8)  .103(8) Uiso 1.000
 H13  -.2323(14)  .033(2) .2383(7)  .079(7) Uiso 1.000
 H14  -.3948(14)  .072(2) .1758(8)  .083(7) Uiso 1.000
 H16  -.5014(15)  .339(3) .2873(8)  .108(8) Uiso 1.000
 H17  -.3412(14)  .290(2) .3473(7)  .084(7) Uiso 1.000
 H102  .27291  .55590  .50002  .133(9) Uiso 1.000
 H105  .4743(12)  .335(2) .5001(7)  .071(6) Uiso 1.000
 H106  .5998(14)  .159(2) .4808(7)  .090(7) Uiso 1.000
 H107  .5734(15)  -.013(3) .4026(8)  .105(7) Uiso 1.000
 H108  .4113(13)  .026(2) .3404(7)  .073(6) Uiso 1.000
 H110  .1959(12)  .261(2) .3462(6)  .053(7) Uiso 1.000
 H111  .2904(14)  .126(3) .2715(8)  .099(6) Uiso 1.000
 H113  .1868(13)  .068(2) .1865(7)  .073(5) Uiso 1.000
 H114  .0275(13)  .066(2) .1181(7)  .085(6) Uiso 1.000
 H116  -.1148(14)  .309(2) .2202(7)  .081(6) Uiso 1.000
 H117  .0445(13)  .299(2) .2851(7)  .068(6) Uiso 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  .0705(9)  .1062(12)  .0765(9)  .0106(9)  .0139(8) -.0316(8)
 O2  .0829(9)  .0769(9)  .0629(9)  .0063(8)  .0130(7) -.0165(7)
 C3  .0730(10)
  .0500(10)
  .0620(10)
  -.0040(10)
   .0200(10)
   -.0020(10)
 C4  .0650(10)
  .0470(10)
  .0660(10)
  -.0050(10)
   .0270(10)
   .0000(10)
 C5  .0700(10)
  .0620(10)
  .0730(10)
  -.0100(10)
   .0230(10)
   -.0030(10)
 C6  .0650(10)
  .073(2)  .089(2)  -.0040(10)
   .0220(10)
   .0040(10)
 C7  .073(2)  .070(2)  .100(2)  .0050(10)
  .043(2)  .0050(10)
 C8  .082(2)  .073(2)  .0740(10)
  -.0010(10)
   .0370(10)
   -.0040(10)
 C9  .0690(10)
  .0530(10)
  .0680(10)
  -.0050(10)
   .0270(10)
   .0030(10)
 C10  .085(2)  .072(2)  .0650(10)
   .0060(10)
   .0310(10)
   -.0090(10)
 C11  .080(2)  .068(2)  .079(2)  -.0020(10)
 .0310(10)
 -.0150(10)
 C12  .0790(10)
   .0590(10)
   .0640(10)
   -.0110(10)
 .0310(10)
 -.0110(10)
 C13  .090(2)  .082(2)  .076(2)  -.0130(10)
 .0360(10)
 -.0240(10)
 C14  .106(2)  .094(2)  .0620(10)
   -.033(2)  .035(2)  -.0200(10)
 C15  .0860(10)
   .0760(10)
   .0560(10)
   -.0200(10)
 .0220(10)
 .0010(10)
 C16  .086(2)  .077(2)  .0730(10)
   -.0030(10)
 .0230(10)
 -.0130(10)
 C17  .088(2)  .078(2)  .0610(10)
   -.0090(10)
 .0270(10)
 -.0180(10)
 Cl18  .1053(5)  .1287(6)  .0727(3) -.0233(4)  .0081(3)  .0080(4)
 O101  .0960(10)
 .0910(10)
 .0560(10)
 .0370(10)
 .0050(10)
 -.0110(10)
 O102  .0698(9)  .1432(15)  .0881(11)  .0102(10)  .0077(8) -.0594(10)
 C103  .0670(10)
 .0630(10)
 .0510(10)
 -.0100(10)
  .0190(10)
  -.0050(10)
 C104  .0590(10)
 .0530(10)
 .0560(10)
 -.0040(10)
  .0170(10)
  .0020(10)
 C105  .0740(10)
 .072(2)  .0650(10)
 -.0010(10)
  .0090(10)
  -.0060(10)
 C106  .072(2)  .092(2)  .088(2)  .012(2)  -.0040(10)
  -.002(2)
 C107  .076(2)  .089(2)  .091(2)  .0210(10)
 .0090(10)
 -.0100(10)
 C108  .081(2)  .071(2)  .0690(10)
 .0100(10)
 .0170(10)
 -.0090(10)
 C109  .0590(10)
 .0610(10)
 .0530(10)
 -.0040(10)
  .0200(10)
  .0020(10)
 C110  .0610(10)
 .0660(10)
 .0580(10)
 .0050(10)
 .0220(10)
 -.0040(10)
 C111  .0650(10)
 .0760(10)
 .0590(10)
 .0030(10)
 .0240(10)
 -.0090(10)
 C112  .0650(10)
 .0560(10)
 .0530(10)
 .0000(10)
 .0190(10)
 -.0040(10)
 C113  .0740(10)
 .076(2)  .0590(10)
 .0110(10)
 .0230(10)
 -.0060(10)
 C114  .093(2)  .079(2)  .0480(10)
 .0000(10)
 .0150(10)
 -.0090(10)
 C115  .0730(10)
 .0600(10)
 .0600(10)
 -.0040(10)
  .0090(10)
  .0050(10)
 C116  .0670(10)
 .077(2)  .0680(10)
 .0080(10)
 .0170(10)
 -.0050(10)
 C117  .0760(10)
 .0790(10)
 .0560(10)
 .0050(10)
 .0200(10)
 -.0150(10)
 Cl118  .0893(4)  .1142(5)  .0771(4) -.0068(4) -.0100(3)  .0069(4)
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 C3 . . 1.214(3) yes
 O2 C3 . . 1.316(3) yes
 C3 C4 . . 1.484(3) yes
 C4 C5 . . 1.383(3) ?
 C4 C9 . . 1.415(3) ?
 C5 C6 . . 1.370(4) ?
 C6 C7 . . 1.370(4) ?
 C7 C8 . . 1.364(4) ?
 C8 C9 . . 1.403(3) ?
 C9 C10 . . 1.460(3) yes
 C10 C11 . . 1.311(4) yes
 C11 C12 . . 1.465(4) yes
 C12 C13 . . 1.390(3) ?
 C12 C17 . . 1.390(3) ?
 C13 C14 . . 1.372(4) ?
 C14 C15 . . 1.359(4) ?
 C15 C16 . . 1.378(3) ?
 C16 C17 . . 1.374(4) ?
 Cl18 C15 . . 1.740(3) yes
 O101 C103 . . 1.203(3) yes
 O102 C103 . . 1.304(3) yes
 C103 C104 . . 1.490(3) yes
 C104 C105 . . 1.389(3) ?
 C104 C109 . . 1.418(3) ?
 C105 C106 . . 1.372(4) ?
 C106 C107 . . 1.369(4) ?
 C107 C108 . . 1.367(4) ?
 C108 C109 . . 1.397(3) ?
 C109 C110 . . 1.460(3) yes
 C110 C111 . . 1.310(3) yes
 C111 C112 . . 1.462(3) yes
 C112 C113 . . 1.400(3) ?
 C112 C117 . . 1.385(3) ?
 C113 C114 . . 1.367(4) ?
 C114 C115 . . 1.368(3) ?
 C115 C116 . . 1.372(3) ?
 C116 C117 . . 1.371(3) ?
 Cl118 C115 . . 1.739(2) yes
 O2 H2 . .  .96 ?
 O102 H102 . .  .96 ?
 C5 H5 . .  .896(17) ?
 C6 H6 . .  .942(17) ?
 C7 H7 . .  .935(18) ?
 C8 H8 . . 1.000(19) ?
 C10 H10 . .  .903(17) ?
 C11 H11 . .  .95(3) ?
 C13 H13 . .  .926(18) ?
 C14 H14 . .  .906(19) ?
 C16 H16 . . 1.00(2) ?
 C17 H17 . .  .910(19) ?
 C105 H105 . .  .969(18) ?
 C106 H106 . .  .887(18) ?
 C107 H107 . . 1.04(2) ?
 C108 H108 . .  .929(17) ?
 C110 H110 . .  .851(15) ?
 C111 H111 . .  .968(19) ?
 C113 H113 . .  .916(17) ?
 C114 H114 . .  .945(19) ?
 C116 H116 . .  .961(18) ?
 C117 H117 . .  .873(17) ?