#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2009313.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_2009313
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
Celecoxib, a COX-II inhibitor
;
loop_
_publ_author_name
  'Vasu Dev, R.'
  'Shashi Rekha, K.'
  'Vyas, K.'
  'Mohanti, S. B.'
  'Rajender Kumar, P.'
  'Om Reddy, G.'
_chemical_formula_moiety  'C17 H14 F3 N3 O2 S'
_chemical_formula_sum  'C17 H14 F3 N3 O2 S'
_chemical_formula_weight  381.37
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '  -x,  -y,  -z'
_cell_length_a  10.136(5)
_cell_length_b  16.778(6)
_cell_length_c  5.066(6)
_cell_angle_alpha  97.62(7)
_cell_angle_beta  100.65(6)
_cell_angle_gamma  95.95(4)
_cell_volume  832.0(10)
_cell_formula_units_Z  2
_cell_measurement_temperature  293.2
_exptl_crystal_density_diffrn  1.522
_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_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
  S(1) 0.65074(9) -0.09233(5) 0.0959(2) 0.0414(2) Uani d ? . 1.000
  F(1) 1.1760(3) 0.40730(10)
  1.3145(5) 0.0783(8) Uani d ? . 1.000
  F(2) 1.1964(3) 0.2846(2) 1.3458(5) 0.0819(9) Uani d ? . 1.000
  F(3) 1.3039(2) 0.3470(2) 1.0988(5) 0.0851(9) Uani d ? . 1.000
  O(1) 0.5123(2) -0.0937(2) 0.1191(6) 0.0572(7) Uani d ? . 1.000
  O(2) 0.6827(3) -0.1084(2) -0.1645(5) 0.0608(8) Uani d ? . 1.000
  N(1) 1.0357(3) 0.2343(2) 0.8402(6) 0.0432(7) Uani d ? . 1.000
  N(2) 0.9332(3) 0.2336(2) 0.6263(6) 0.0402(7) Uani d ? . 1.000
  N(3) 0.7121(3) -0.1574(2) 0.2699(6) 0.0460(9) Uani d ? D 1.000
  C(1) 1.0715(3) 0.3125(2) 0.9390(7) 0.0396(8) Uani d ? . 1.000
  C(2) 0.9950(4) 0.3615(2) 0.7922(7) 0.0442(9) Uani d ? . 1.000
  C(3) 0.9056(3) 0.3104(2) 0.5874(7) 0.0397(8) Uani d ? . 1.000
  C(4) 1.1881(4) 0.3369(2) 1.1727(8) 0.0510(9) Uani d ? . 1.000
  C(5) 0.8062(3) 0.3312(2) 0.3667(7) 0.0395(8) Uani d ? . 1.000
  C(6) 0.7018(4) 0.2784(2) 0.1960(8) 0.0520(10)
  Uani d ? . 1.000
  C(7) 0.6139(4) 0.3037(2) -0.0065(8) 0.0570(10)
  Uani d ? . 1.000
  C(8) 0.6281(4) 0.3836(2) -0.0543(8) 0.0480(10)
  Uani d ? . 1.000
  C(9) 0.7297(4) 0.4372(2) 0.1186(9) 0.0570(10)
  Uani d ? . 1.000
  C(10) 0.8179(4) 0.4112(2) 0.3212(9) 0.0540(10)
  Uani d ? . 1.000
  C(11) 0.5334(4) 0.4106(3) -0.2810(9) 0.0660(10)
  Uani d ? . 1.000
  C(12) 0.8649(3) 0.1550(2) 0.4909(7) 0.0397(8) Uani d ? . 1.000
  C(13) 0.7540(4) 0.1235(2) 0.5787(8) 0.0470(10)
  Uani d ? . 1.000
  C(14) 0.6890(4) 0.0476(2) 0.4583(8) 0.0470(10)
  Uani d ? . 1.000
  C(15) 0.7363(3) 0.0052(2) 0.2508(7) 0.0387(8) Uani d ? . 1.000
  C(16) 0.8480(4) 0.0371(2) 0.1662(8) 0.0520(10)
  Uani d ? . 1.000
  C(17) 0.9145(4) 0.1132(2) 0.2871(8) 0.0520(10)
  Uani d ? . 1.000
  H(1) 1.0017 0.4199 0.8290 0.052 Uiso c ? . 1.000
  H(2) 0.6877 0.2224 0.2256 0.061 Uiso c ? . 1.000
  H(3) 0.5423 0.2645 -0.1252 0.068 Uiso c ? . 1.000
  H(4) 0.7375 0.4937 0.0965 0.069 Uiso c ? . 1.000
  H(5) 0.8907 0.4507 0.4366 0.066 Uiso c ? . 1.000
  H(6) 0.4852 0.4510 -0.2119 0.079 Uiso c ? . 1.000
  H(7) 0.5843 0.4323 -0.4044 0.079 Uiso c ? . 1.000
  H(8) 0.4710 0.3654 -0.3820 0.079 Uiso c ? . 1.000
  H(9) 0.7228 0.1538 0.7252 0.056 Uiso c ? . 1.000
  H(10) 0.6100 0.0235 0.5198 0.058 Uiso c ? . 1.000
  H(11) 0.8801 0.0065 0.0210 0.062 Uiso c ? . 1.000
  H(12) 0.9917 0.1377 0.2268 0.064 Uiso c ? . 1.000
  H(13) 0.698(5) -0.147(3) 0.435(4) 0.079 Uiso d ? D 1.000
  H(14) 0.790(2) -0.171(3) 0.247(9) 0.073 Uiso d ? D 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
  S(1) 0.0426(5) 0.0324(4) 0.0433(5) 0.0051(3) -0.0020(4) -0.0010(3)
  F(1) 0.083(2) 0.0590(10)
  0.073(2) 0.0180(10)
  -0.0190(10)
  -0.0210(10)
  F(2) 0.087(2) 0.069(2) 0.075(2) -0.0010(10)
  -0.0260(10)
  0.0270(10)
  F(3) 0.0340(10)
  0.130(2) 0.080(2) -0.0040(10)
  0.0020(10)
  -0.001(2)
  O(1) 0.0370(10)
  0.0460(10)
  0.079(2) 0.0000(10)
  -0.0040(10)
  -0.0010(10)
  O(2) 0.084(2) 0.0460(10)
  0.0440(10)
  -0.0070(10)
  0.0090(10)
  -0.0060(10)
  N(1) 0.0340(10)
  0.0370(10)
  0.054(2) 0.0070(10)
  -0.0040(10)
  0.0030(10)
  N(2) 0.0330(10)
  0.0320(10)
  0.051(2) 0.0070(10)
  -0.0040(10)
  0.0040(10)
  N(3) 0.055(2) 0.0360(10)
  0.047(2) 0.0160(10)
  0.007(2) 0.0020(10)
  C(1) 0.031(2) 0.0390(10)
  0.046(2) 0.0070(10)
  0.0040(10)
  0.0010(10)
  C(2) 0.040(2) 0.036(2) 0.051(2) 0.0090(10)
  -0.0030(10)
  -0.0010(10)
  C(3) 0.034(2) 0.0330(10)
  0.050(2) 0.0090(10)
  0.0030(10)
  0.0020(10)
  C(4) 0.038(2) 0.050(2) 0.055(2) 0.005(2) -0.0080(10)
  -0.0010(10)
  C(5) 0.028(2) 0.0390(10)
  0.049(2) 0.0090(10)
  0.0030(10)
  0.0030(10)
  C(6) 0.048(2) 0.030(2) 0.066(2) 0.0040(10)
  -0.010(2) 0.0020(10)
  C(7) 0.049(2) 0.045(2) 0.065(2) 0.009(2) -0.012(2) -0.002(2)
  C(8) 0.038(2) 0.049(2) 0.056(2) 0.0130(10)
  0.0080(10)
  0.007(2)
  C(9) 0.046(2) 0.047(2) 0.076(3) 0.0120(10)
  -0.005(2) 0.015(2)
  C(10) 0.040(2) 0.039(2) 0.075(3) 0.0030(10)
  -0.006(2) 0.007(2)
  C(11) 0.055(3) 0.075(3) 0.067(3) 0.020(2) -0.006(2) 0.018(2)
  C(12) 0.034(2) 0.0310(10)
  0.049(2) 0.0070(10)
  -0.0030(10)
  0.0030(10)
  C(13) 0.040(2) 0.039(2) 0.057(2) 0.0060(10)
  0.011(2) -0.009(2)
  C(14) 0.043(2) 0.038(2) 0.059(2) 0.0010(10)
  0.016(2) -0.0020(10)
  C(15) 0.038(2) 0.0280(10)
  0.046(2) 0.0060(10)
  -0.0010(10)
  0.0040(10)
  C(16) 0.045(2) 0.045(2) 0.063(3) 0.0000(10)
  0.018(2) -0.009(2)
  C(17) 0.047(2) 0.044(2) 0.063(2) 0.0010(10)
  0.019(2) -0.002(2)
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
  S(1) O(1) . . 1.428(4) no
  S(1) O(2) . . 1.414(4) no
  S(1) N(3) . . 1.596(4) no
  S(1) C(15) . . 1.777(4) no
  F(1) C(4) . . 1.329(6) no
  F(2) C(4) . . 1.319(6) no
  F(3) C(4) . . 1.298(6) no
  N(1) N(2) . . 1.353(5) no
  N(1) C(1) . . 1.328(5) no
  N(2) C(3) . . 1.378(5) no
  N(2) C(12) . . 1.444(5) no
  N(3) H(13) . . 0.872(9) no
  N(3) H(14) . . 0.871(9) no
  C(1) C(2) . . 1.383(6) no
  C(1) C(4) . . 1.490(6) no
  C(2) C(3) . . 1.375(6) no
  C(2) H(1) . . 0.97 no
  C(3) C(5) . . 1.465(6) no
  C(5) C(6) . . 1.385(6) no
  C(5) C(10) . . 1.388(6) no
  C(6) C(7) . . 1.372(7) no
  C(6) H(2) . . 0.97 no
  C(7) C(8) . . 1.391(7) no
  C(7) H(3) . . 0.98 no
  C(8) C(9) . . 1.379(7) no
  C(8) C(11) . . 1.505(7) no
  C(9) C(10) . . 1.380(7) no
  C(9) H(4) . . 0.97 no
  C(10) H(5) . . 0.98 no
  C(11) H(6) . . 0.94 no
  C(11) H(7) . . 0.97 no
  C(11) H(8) . . 0.96 no
  C(12) C(13) . . 1.366(7) no
  C(12) C(17) . . 1.372(7) no
  C(13) C(14) . . 1.378(6) no
  C(13) H(9) . . 0.96 no
  C(14) C(15) . . 1.378(6) no
  C(14) H(10) . . 0.98 no
  C(15) C(16) . . 1.367(7) no
  C(16) C(17) . . 1.387(7) no
  C(16) H(11) . . 0.97 no
  C(17) H(12) . . 0.96 no