#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202445.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_2202445
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1731
_journal_page_last  o1732
_publ_section_title
;
5-[5-(4-Methoxyphenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]-2-sulfamoylbenzyl
propionate: a novel 1,5-diraylpyrazole class of COX-2 inhibitor
;
loop_
_publ_author_name
  'K. Vyas'
  'A. Sivalakshmidevi'
  'S. K. Singh'
  'Y. Koteswar Rao'
  'G. Om Reddy'
_chemical_formula_moiety  'C21 H20 F3 N3 O5 S'
_chemical_formula_sum  'C21 H20 F3 N3 O5 S'
_chemical_formula_iupac  'C21 H20 F3 N3 O5 S'
_chemical_formula_weight  483.46
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,-y,-z'
_cell_length_a  10.4490(8)
_cell_length_b  12.0126(8)
_cell_length_c  9.2196(9)
_cell_angle_alpha  111.068(6)
_cell_angle_beta  94.851(7)
_cell_angle_gamma  86.328(6)
_cell_volume  1075.3(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  298.1
_exptl_crystal_density_diffrn  1.493
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
  S1 0.18380(5) 0.50840(5) 0.66650(6) 0.0382(2) Uani . . 1.000 S
  F1 0.8874(2) 0.1482(2) 0.1314(3) 0.0891(8) Uani . . 1.000 F
  F2 0.8443(2) -0.0226(2) -0.0309(2) 0.0769(6) Uani . . 1.000 F
  F3 0.9287(2) -0.0067(3) 0.1899(3) 0.0923(10) Uani . . 1.000 F
  O1 0.0637(2) 0.4506(2) 0.6258(2) 0.0515(6) Uani . . 1.000 O
  O2 0.2303(2) 0.5540(2) 0.8257(2) 0.0541(6) Uani . . 1.000 O
  O3 0.62240(10) 0.48760(10) 0.7610(2) 0.0456(5) Uani . . 1.000 O
  O4 0.6274(2) 0.6555(2) 0.9685(3) 0.0666(6) Uani . . 1.000 O
  O5 0.1156(2) -0.2392(2) 0.3089(3) 0.0655(6) Uani . . 1.000 O
  N1 0.1731(3) 0.6152(2) 0.6023(3) 0.0524(8) Uani . . 1.000 N
  N2 0.5485(2) 0.1316(2) 0.2981(2) 0.0355(5) Uani . . 1.000 N
  N3 0.6629(2) 0.1594(2) 0.2621(2) 0.0388(6) Uani . . 1.000 N
  C1 0.3001(2) 0.4023(2) 0.5599(3) 0.0331(6) Uani . . 1.000 C
  C2 0.4310(2) 0.4039(2) 0.6095(2) 0.0337(6) Uani . . 1.000 C
  C3 0.5121(2) 0.3134(2) 0.5203(3) 0.0350(6) Uani . . 1.000 C
  C4 0.4639(2) 0.2267(2) 0.3838(2) 0.0338(6) Uani . . 1.000 C
  C5 0.3364(2) 0.2294(2) 0.3317(3) 0.0386(6) Uani . . 1.000 C
  C6 0.2544(2) 0.3165(2) 0.4222(3) 0.0385(6) Uani . . 1.000 C
  C7 0.4847(2) 0.4983(2) 0.7569(3) 0.0427(6) Uani . . 1.000 C
  C8 0.6835(2) 0.5741(2) 0.8778(3) 0.0390(6) Uani . . 1.000 C
  C9 0.8258(2) 0.5535(2) 0.8770(3) 0.0472(6) Uani . . 1.000 C
  C10 0.9007(3) 0.6567(3) 0.9823(5) 0.0771(12) Uani . . 1.000 C
  C11 0.5291(2) 0.0110(2) 0.2389(3) 0.0364(6) Uani . . 1.000 C
  C12 0.6359(2) -0.0411(2) 0.1589(3) 0.0423(6) Uani . . 1.000 C
  C13 0.7139(2) 0.0538(2) 0.1772(3) 0.0396(6) Uani . . 1.000 C
  C14 0.4189(2) -0.0486(2) 0.2641(3) 0.0363(6) Uani . . 1.000 C
  C15 0.3527(2) -0.0061(2) 0.3991(3) 0.0379(6) Uani . . 1.000 C
  C16 0.2506(2) -0.0669(2) 0.4177(3) 0.0412(6) Uani . . 1.000 C
  C17 0.2146(2) -0.1728(2) 0.3008(3) 0.0446(6) Uani . . 1.000 C
  C18 0.2826(3) -0.2183(2) 0.1676(3) 0.0505(8) Uani . . 1.000 C
  C19 0.3826(3) -0.1570(2) 0.1495(3) 0.0453(6) Uani . . 1.000 C
  C20 0.0217(3) -0.1832(3) 0.4141(4) 0.0625(12) Uani . . 1.000 C
  C21 0.8434(2) 0.0449(2) 0.1169(3) 0.0450(6) Uani . . 1.000 C
  H1 0.6006 0.3104 0.5527 0.040 Uiso calc . 1.000 H
  H2 0.3060 0.1724 0.2353 0.044 Uiso calc . 1.000 H
  H3 0.1659 0.3183 0.3893 0.044 Uiso calc . 1.000 H
  H4 0.4551 0.4878 0.8456 0.046 Uiso calc . 1.000 H
  H5 0.4577 0.5753 0.7566 0.046 Uiso calc . 1.000 H
  H6 0.8468 0.4866 0.9075 0.054 Uiso calc . 1.000 H
  H7 0.8501 0.5360 0.7740 0.054 Uiso calc . 1.000 H
  H8 0.9900 0.6370 0.9749 0.081 Uiso calc . 1.000 H
  H9 0.8808 0.7245 0.9535 0.082 Uiso calc . 1.000 H
  H10 0.8791 0.6741 1.0864 0.082 Uiso calc . 1.000 H
  H11 0.6532 -0.1237 0.1045 0.048 Uiso calc . 1.000 H
  H12 0.3782 0.0654 0.4803 0.043 Uiso calc . 1.000 H
  H13 0.2050 -0.0360 0.5096 0.048 Uiso calc . 1.000 H
  H14 0.2584 -0.2911 0.0880 0.056 Uiso calc . 1.000 H
  H15 0.4289 -0.1892 0.0582 0.051 Uiso calc . 1.000 H
  H16 0.0608 -0.1542 0.5170 0.077 Uiso calc . 1.000 H
  H17 -0.0187 -0.1185 0.3895 0.077 Uiso calc . 1.000 H
  H18 -0.0407 -0.2393 0.4073 0.077 Uiso calc . 1.000 H
  H19 0.115(4) 0.611(3) 0.531(5) 0.070(10) Uiso . . 1.000 H
  H20 0.226(3) 0.671(3) 0.644(4) 0.062(9) Uiso . . 1.000 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
  S1 0.0296(4) 0.0354(4) 0.0413(4) -0.0024(2) 0.0072(2) 0.0024(3)
  F1 0.0770(10) 0.0500(10) 0.129(2) -0.0149(9) 0.0570(10) 0.0050(10)
  F2 0.0650(10) 0.0880(10) 0.0540(10) -0.0110(10) 0.0285(8) -0.0102(9)
  F3 0.0500(10) 0.146(2) 0.098(2) 0.0200(10) 0.0180(10) 0.065(2)
  O1 0.0337(9) 0.0480(10) 0.0660(10) -0.0080(7) 0.0111(8) 0.0092(9)
  O2 0.0440(10) 0.0640(10) 0.0400(10) 0.0033(8) 0.0107(7) 0.0003(8)
  O3 0.0309(8) 0.0418(9) 0.0459(9) -0.0047(7) 0.0025(7) -0.0068(7)
  O4 0.0460(10) 0.0560(10) 0.0630(10) -0.0041(9) 0.0025(9) -0.0210(10)
  O5 0.0640(10) 0.0440(10) 0.0800(10) -0.0232(9) 0.0200(10) 0.0050(10)
  N1 0.0480(10) 0.0350(10) 0.067(2) -0.0055(9) -0.0060(10) 0.0110(10)
  N2 0.0360(10) 0.0296(9) 0.0348(9) -0.0035(7) 0.0088(7) 0.0022(7)
  N3 0.0390(10) 0.0340(10) 0.0380(10) -0.0043(8) 0.0113(8) 0.0040(8)
  C1 0.0320(10) 0.0290(10) 0.0360(10) -0.0009(8) 0.0056(8) 0.0082(8)
  C2 0.0340(10) 0.0310(10) 0.0320(10) -0.0039(8) 0.0059(8) 0.0049(8)
  C3 0.0310(10) 0.0330(10) 0.0360(10) -0.0037(8) 0.0047(8) 0.0053(9)
  C4 0.0380(10) 0.0270(10) 0.0320(10) -0.0013(8) 0.0079(8) 0.0038(8)
  C5 0.0420(10) 0.0350(10) 0.0320(10) -0.0042(9) -0.0010(9) 0.0041(9)
  C6 0.0360(10) 0.0380(10) 0.0360(10) -0.0013(9) -0.0002(9) 0.0072(9)
  C7 0.0320(10) 0.0410(10) 0.0410(10) -0.0022(9) 0.0049(9) -0.0030(10)
  C8 0.0400(10) 0.0340(10) 0.0340(10) -0.0043(9) 0.0024(9) 0.0009(9)
  C9 0.0390(10) 0.0420(10) 0.0530(10) -0.0030(10) 0.0010(10) 0.0080(10)
  C10 0.045(2) 0.070(2) 0.089(2) -0.0140(10) -0.012(2) -0.003(2)
  C11 0.0410(10) 0.0290(10) 0.0330(10) -0.0046(8) 0.0057(9) 0.0024(8)
  C12 0.0450(10) 0.0320(10) 0.0420(10) -0.0029(9) 0.0110(10) 0.0017(9)
  C13 0.0410(10) 0.0360(10) 0.0360(10) -0.0023(9) 0.0115(9) 0.0036(9)
  C14 0.0380(10) 0.0320(10) 0.0350(10) -0.0034(9) 0.0042(9) 0.0066(9)
  C15 0.0410(10) 0.0320(10) 0.0350(10) -0.0050(9) 0.0030(9) 0.0044(9)
  C16 0.0430(10) 0.0350(10) 0.0420(10) -0.0045(9) 0.0070(10) 0.0080(10)
  C17 0.0440(10) 0.0350(10) 0.0520(10) -0.0100(10) 0.0020(10) 0.0110(10)
  C18 0.057(2) 0.0330(10) 0.0490(10) -0.0120(10) 0.0030(10) -0.0020(10)
  C19 0.0510(10) 0.0350(10) 0.0410(10) -0.0040(10) 0.0090(10) 0.0010(10)
  C20 0.061(2) 0.055(2) 0.075(2) -0.0180(10) 0.0170(10) 0.0220(10)
  C21 0.0430(10) 0.0400(10) 0.0440(10) -0.0030(10) 0.0160(10) 0.0020(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
  S1 O1 . . 1.429(2) no
  S1 O2 . . 1.4233(18) no
  S1 N1 . . 1.589(3) no
  S1 C1 . . 1.780(2) no
  F1 C21 . . 1.309(4) no
  F2 C21 . . 1.312(3) no
  F3 C21 . . 1.326(4) no
  O3 C7 . . 1.435(2) no
  O3 C8 . . 1.346(3) no
  O4 C8 . . 1.192(3) no
  O5 C17 . . 1.369(3) no
  O5 C20 . . 1.401(4) no
  N2 N3 . . 1.360(3) no
  N2 C4 . . 1.432(3) no
  N2 C11 . . 1.374(4) no
  N3 C13 . . 1.333(3) no
  N1 H19 . . 0.85(4) no
  N1 H20 . . 0.85(4) no
  C1 C2 . . 1.404(3) no
  C1 C6 . . 1.386(4) no
  C2 C7 . . 1.514(3) no
  C2 C3 . . 1.390(3) no
  C3 C4 . . 1.393(3) no
  C4 C5 . . 1.380(3) no
  C5 C6 . . 1.380(3) no
  C8 C9 . . 1.492(3) no
  C9 C10 . . 1.491(5) no
  C11 C12 . . 1.378(3) no
  C11 C14 . . 1.471(3) no
  C12 C13 . . 1.396(3) no
  C13 C21 . . 1.489(3) no
  C14 C19 . . 1.401(4) no
  C14 C15 . . 1.390(3) no
  C15 C16 . . 1.386(3) no
  C16 C17 . . 1.389(4) no
  C17 C18 . . 1.388(4) no
  C18 C19 . . 1.371(4) no
  C3 H1 . . 0.950 no
  C5 H2 . . 0.950 no
  C6 H3 . . 0.950 no
  C7 H4 . . 0.950 no
  C7 H5 . . 0.951 no
  C9 H6 . . 0.950 no
  C9 H7 . . 0.949 no
  C10 H8 . . 0.950 no
  C10 H9 . . 0.949 no
  C10 H10 . . 0.950 no
  C12 H11 . . 0.950 no
  C15 H12 . . 0.950 no
  C16 H13 . . 0.950 no
  C18 H14 . . 0.950 no
  C19 H15 . . 0.950 no
  C20 H16 . . 0.950 no
  C20 H17 . . 0.950 no
  C20 H18 . . 0.950 no
_cod_database_code 2202445