#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012888.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012888
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o450
_journal_page_last  o454
_publ_section_title
;
Diethyl
{3-[\b-(2,4-dichlorophenyl)vinyl]-N-phenylsulfonyl-indol-2-ylmethyl}phosphonate
and diethyl
{3-[\b-(4-bromophenyl)vinyl]-N-phenylsulfonyl-indol-2-ylmethyl}phosphonate
;
loop_
_publ_author_name
  'Sethu Sankar, K.'
  'Kannadasan, S.'
  'Velmurugan, D.'
  'Srinivasan, P. C.'
  'Moon, Jib-Kim'
_chemical_formula_moiety  'C27 H26 Cl2 N O5 P S'
_chemical_formula_sum  'C27 H26 Cl2 N O5 P S'
_chemical_formula_weight  578.42
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  16.608(2)
_cell_length_b  8.3570(10)
_cell_length_c  19.647(5)
_cell_angle_alpha  90
_cell_angle_beta  93.300(10)
_cell_angle_gamma  90
_cell_volume  2722.4(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.411
_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
  P1 0.31476(6) -0.40244(15) 0.20785(5) 0.0529(3) Uani d . 1 . . P
  S1 0.56810(6) -0.49475(14) 0.26025(5) 0.0531(3) Uani d . 1 . . S
  Cl1 0.03728(8) -1.20568(18) -0.03072(7) 0.0844(5) Uani d . 1 . . Cl
  Cl2 0.31530(9) -0.9612(2) -0.10733(6) 0.0956(5) Uani d . 1 . . Cl
  N1 0.51749(18) -0.5255(4) 0.18548(15) 0.0450(8) Uani d . 1 . . N
  O1 0.26812(19) -0.3479(4) 0.26437(15) 0.0714(9) Uani d . 1 . . O
  O2 0.64009(18) -0.4126(4) 0.24564(16) 0.0708(9) Uani d . 1 . . O
  O3 0.51363(18) -0.4218(4) 0.30449(15) 0.0671(9) Uani d . 1 . . O
  O4 0.3698(2) -0.2740(4) 0.17576(16) 0.0719(9) Uani d . 1 . . O
  O5 0.26459(18) -0.4594(5) 0.14249(17) 0.0866(11) Uani d . 1 . . O
  C1 0.4410(2) -0.6030(4) 0.17979(18) 0.0419(9) Uani d . 1 . . C
  C2 0.4326(2) -0.6851(5) 0.11981(18) 0.0419(9) Uani d . 1 . . C
  C3 0.5067(2) -0.6632(5) 0.08469(18) 0.0432(9) Uani d . 1 . . C
  C4 0.5578(2) -0.5671(5) 0.12538(19) 0.0475(10) Uani d . 1 . . C
  C5 0.6326(2) -0.5164(6) 0.1048(2) 0.0642(13) Uani d . 1 . . C
  H5 0.6655 -0.4485 0.1316 0.077 Uiso calc R 1 . . H
  C6 0.6557(3) -0.5718(7) 0.0426(3) 0.0774(15) Uani d . 1 . . C
  H6 0.7062 -0.5439 0.0283 0.093 Uiso calc R 1 . . H
  C7 0.6061(3) -0.6668(7) 0.0015(2) 0.0742(14) Uani d . 1 . . C
  H7 0.6229 -0.6995 -0.0407 0.089 Uiso calc R 1 . . H
  C8 0.5322(3) -0.7139(6) 0.0219(2) 0.0611(12) Uani d . 1 . . C
  H8 0.4992 -0.7792 -0.0061 0.073 Uiso calc R 1 . . H
  C9 0.5921(2) -0.6862(5) 0.2918(2) 0.0502(10) Uani d . 1 . . C
  C10 0.5567(3) -0.7392(7) 0.3484(3) 0.0860(17) Uani d . 1 . . C
  H10 0.5200 -0.6750 0.3697 0.103 Uiso calc R 1 . . H
  C11 0.5760(4) -0.8894(8) 0.3737(3) 0.114(2) Uani d . 1 . . C
  H11 0.5531 -0.9258 0.4130 0.137 Uiso calc R 1 . . H
  C12 0.6287(4) -0.9853(7) 0.3412(3) 0.0975(19) Uani d . 1 . . C
  H12 0.6401 -1.0878 0.3575 0.117 Uiso calc R 1 . . H
  C13 0.6642(3) -0.9304(7) 0.2854(3) 0.0803(15) Uani d . 1 . . C
  H13 0.7006 -0.9948 0.2638 0.096 Uiso calc R 1 . . H
  C14 0.6466(3) -0.7804(6) 0.2607(2) 0.0611(12) Uani d . 1 . . C
  H14 0.6717 -0.7425 0.2227 0.073 Uiso calc R 1 . . H
  C15 0.3776(2) -0.5725(5) 0.22920(19) 0.0484(10) Uani d . 1 . . C
  H15A 0.4036 -0.5561 0.2741 0.058 Uiso calc R 1 . . H
  H15B 0.3437 -0.6668 0.2314 0.058 Uiso calc R 1 . . H
  C16 0.4035(4) -0.1393(7) 0.2100(3) 0.0906(17) Uani d . 1 . . C
  H16A 0.4166 -0.1662 0.2574 0.109 Uiso calc R 1 . . H
  H16B 0.3644 -0.0530 0.2087 0.109 Uiso calc R 1 . . H
  C17 0.4773(4) -0.0859(7) 0.1778(4) 0.117(2) Uani d . 1 . . C
  H17A 0.5167 -0.1701 0.1806 0.175 Uiso calc R 1 . . H
  H17B 0.4988 0.0070 0.2012 0.175 Uiso calc R 1 . . H
  H17C 0.4644 -0.0601 0.1309 0.175 Uiso calc R 1 . . H
  C18 0.1903(4) -0.4472(13) 0.1260(4) 0.183(5) Uani d . 1 . . C
  H18A 0.1804 -0.3347 0.1167 0.220 Uiso calc R 1 . . H
  H18B 0.1623 -0.4726 0.1666 0.220 Uiso calc R 1 . . H
  C19 0.1507(4) -0.5314(8) 0.0726(3) 0.113(2) Uani d . 1 . . C
  H19A 0.1897 -0.5859 0.0468 0.170 Uiso calc R 1 . . H
  H19B 0.1205 -0.4580 0.0435 0.170 Uiso calc R 1 . . H
  H19C 0.1147 -0.6081 0.0908 0.170 Uiso calc R 1 . . H
  C20 0.3606(2) -0.7712(5) 0.0984(2) 0.0480(10) Uani d . 1 . . C
  H20 0.3218 -0.7783 0.1306 0.058 Uiso calc R 1 . . H
  C21 0.3420(2) -0.8415(5) 0.0395(2) 0.0553(11) Uani d . 1 . . C
  H21 0.3790 -0.8328 0.0059 0.066 Uiso calc R 1 . . H
  C22 0.2681(2) -0.9320(5) 0.0224(2) 0.0526(11) Uani d . 1 . . C
  C23 0.2112(3) -0.9613(6) 0.0703(2) 0.0683(13) Uani d . 1 . . C
  H23 0.2209 -0.9241 0.1147 0.082 Uiso calc R 1 . . H
  C24 0.1414(3) -1.0431(6) 0.0539(2) 0.0718(14) Uani d . 1 . . C
  H24 0.1043 -1.0594 0.0869 0.086 Uiso calc R 1 . . H
  C25 0.1258(3) -1.1009(5) -0.0101(2) 0.0598(11) Uani d . 1 . . C
  C26 0.1792(3) -1.0764(5) -0.0599(2) 0.0592(12) Uani d . 1 . . C
  H26 0.1686 -1.1155 -0.1038 0.071 Uiso calc R 1 . . H
  C27 0.2494(2) -0.9919(5) -0.0432(2) 0.0541(11) Uani d . 1 . . C
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
  P1 0.0492(6) 0.0631(8) 0.0476(6) 0.0046(6) 0.0149(5) -0.0059(5)
  S1 0.0511(6) 0.0574(7) 0.0501(6) -0.0019(5) -0.0033(5) -0.0076(5)
  Cl1 0.0758(8) 0.0931(10) 0.0822(9) -0.0294(7) -0.0151(7) 0.0024(7)
  Cl2 0.0972(10) 0.1380(13) 0.0536(7) -0.0354(10) 0.0225(7) -0.0246(8)
  N1 0.0407(17) 0.055(2) 0.0393(18) -0.0023(16) 0.0038(14) -0.0019(15)
  O1 0.077(2) 0.077(2) 0.0630(19) 0.0183(18) 0.0294(16) -0.0064(17)
  O2 0.0604(19) 0.074(2) 0.077(2) -0.0223(17) -0.0056(16) -0.0020(18)
  O3 0.073(2) 0.071(2) 0.0568(18) 0.0150(17) -0.0024(15) -0.0225(16)
  O4 0.087(2) 0.062(2) 0.069(2) -0.0063(18) 0.0265(17) -0.0052(17)
  O5 0.0495(18) 0.137(3) 0.072(2) 0.016(2) -0.0050(16) -0.031(2)
  C1 0.040(2) 0.046(2) 0.040(2) 0.0026(18) 0.0046(16) 0.0041(18)
  C2 0.042(2) 0.048(2) 0.036(2) 0.0035(18) 0.0031(16) 0.0038(18)
  C3 0.045(2) 0.047(2) 0.038(2) 0.0074(19) 0.0075(17) 0.0037(18)
  C4 0.046(2) 0.055(3) 0.042(2) 0.003(2) 0.0066(18) 0.0086(19)
  C5 0.043(2) 0.085(3) 0.065(3) -0.006(2) 0.011(2) 0.014(3)
  C6 0.053(3) 0.115(4) 0.067(3) 0.000(3) 0.025(3) 0.022(3)
  C7 0.066(3) 0.105(4) 0.054(3) 0.012(3) 0.019(2) -0.002(3)
  C8 0.057(3) 0.083(3) 0.044(2) 0.006(2) 0.011(2) -0.003(2)
  C9 0.041(2) 0.065(3) 0.044(2) 0.001(2) -0.0017(18) 0.001(2)
  C10 0.075(3) 0.106(4) 0.080(4) 0.031(3) 0.028(3) 0.024(3)
  C11 0.114(5) 0.126(6) 0.107(5) 0.035(5) 0.043(4) 0.058(4)
  C12 0.104(4) 0.088(4) 0.101(5) 0.033(4) 0.015(4) 0.037(4)
  C13 0.070(3) 0.086(4) 0.085(4) 0.026(3) 0.004(3) 0.002(3)
  C14 0.054(3) 0.075(3) 0.055(3) 0.011(2) 0.007(2) 0.004(2)
  C15 0.050(2) 0.058(3) 0.038(2) -0.005(2) 0.0091(17) -0.0047(19)
  C16 0.105(4) 0.063(3) 0.105(4) 0.000(3) 0.016(4) -0.013(3)
  C17 0.089(4) 0.074(4) 0.184(7) -0.013(3) -0.016(5) 0.035(4)
  C18 0.074(4) 0.319(13) 0.150(7) 0.056(6) -0.032(5) -0.121(8)
  C19 0.085(4) 0.132(6) 0.117(5) -0.002(4) -0.035(4) 0.009(4)
  C20 0.046(2) 0.052(2) 0.047(2) 0.005(2) 0.0079(18) -0.001(2)
  C21 0.053(2) 0.072(3) 0.042(2) -0.007(2) 0.0063(19) -0.005(2)
  C22 0.060(3) 0.055(3) 0.043(2) -0.004(2) 0.002(2) -0.002(2)
  C23 0.070(3) 0.086(4) 0.049(3) -0.021(3) 0.005(2) -0.010(2)
  C24 0.072(3) 0.095(4) 0.049(3) -0.025(3) 0.008(2) -0.003(3)
  C25 0.053(3) 0.062(3) 0.063(3) -0.007(2) -0.005(2) 0.008(2)
  C26 0.071(3) 0.055(3) 0.050(2) -0.003(2) -0.011(2) -0.005(2)
  C27 0.058(3) 0.058(3) 0.046(2) 0.003(2) 0.003(2) -0.002(2)
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
  P1 O1 . 1.463(3) yes
  P1 O4 . 1.566(3) yes
  P1 O5 . 1.564(3) yes
  P1 C15 . 1.798(4) yes
  S1 O2 . 1.422(3) yes
  S1 O3 . 1.427(3) yes
  S1 N1 . 1.670(3) yes
  S1 C9 . 1.754(4) yes
  Cl1 C25 . 1.739(4) yes
  Cl2 C27 . 1.735(4) yes
  N1 C1 . 1.424(5) yes
  N1 C4 . 1.433(5) yes
  O4 C16 . 1.410(6) ?
  O5 C18 . 1.261(6) ?
  C1 C2 . 1.364(5) ?
  C1 C15 . 1.495(5) ?
  C2 C20 . 1.438(5) ?
  C2 C3 . 1.457(5) ?
  C3 C4 . 1.387(5) ?
  C3 C8 . 1.394(5) ?
  C4 C5 . 1.396(5) ?
  C5 C6 . 1.380(6) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.373(7) ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.371(6) ?
  C7 H7 . 0.9300 ?
  C8 H8 . 0.9300 ?
  C9 C10 . 1.361(6) ?
  C9 C14 . 1.371(6) ?
  C10 C11 . 1.382(8) ?
  C10 H10 . 0.9300 ?
  C11 C12 . 1.371(8) ?
  C11 H11 . 0.9300 ?
  C12 C13 . 1.355(7) ?
  C12 H12 . 0.9300 ?
  C13 C14 . 1.370(7) ?
  C13 H13 . 0.9300 ?
  C14 H14 . 0.9300 ?
  C15 H15A . 0.9700 ?
  C15 H15B . 0.9700 ?
  C16 C17 . 1.480(8) ?
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  C17 H17A . 0.9600 ?
  C17 H17B . 0.9600 ?
  C17 H17C . 0.9600 ?
  C18 C19 . 1.395(9) yes
  C18 H18A . 0.9700 ?
  C18 H18B . 0.9700 ?
  C19 H19A . 0.9600 ?
  C19 H19B . 0.9600 ?
  C19 H19C . 0.9600 ?
  C20 C21 . 1.320(5) ?
  C20 H20 . 0.9300 ?
  C21 C22 . 1.464(6) ?
  C21 H21 . 0.9300 ?
  C22 C23 . 1.395(6) ?
  C22 C27 . 1.400(5) ?
  C23 C24 . 1.368(6) ?
  C23 H23 . 0.9300 ?
  C24 C25 . 1.358(6) ?
  C24 H24 . 0.9300 ?
  C25 C26 . 1.373(6) ?
  C26 C27 . 1.385(6) ?
  C26 H26 . 0.9300 ?