#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/93/2009313.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009313
loop_
_publ_author_name
'Vasu Dev, R.'
'Shashi Rekha, K.'
'Vyas, K.'
'Mohanti, S. B.'
'Rajender Kumar, P.'
'Om Reddy, G.'
_publ_section_title
;
 Celecoxib, a COX-II inhibitor
;
_journal_coeditor_code           QA0186
_journal_data_validation_number  IUC9900161
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_paper_doi               10.1107/S0108270199098200
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C17 H14 F3 N3 O2 S'
_chemical_formula_sum            'C17 H14 F3 N3 O2 S'
_chemical_formula_weight         381.37
_chemical_name_common            Celecoxib
_chemical_name_systematic
;
4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyazol-1-yl]benezenesulfonamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                97.62(7)
_cell_angle_beta                 100.65(6)
_cell_angle_gamma                95.95(4)
_cell_formula_units_Z            2
_cell_length_a                   10.136(5)
_cell_length_b                   16.778(6)
_cell_length_c                   5.066(6)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293.2
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      20.6
_cell_volume                     831.9(11)
_computing_cell_refinement       'MSC/AFC diffractometer control software'
_computing_data_collection       'MSC/AFC diffractometer control software'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_diffrn_ambient_temperature      293.2
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.08229
_diffrn_reflns_av_sigmaI/netI    0.100
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3330
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         70.12
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        1.15
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.194
_exptl_absorpt_correction_T_max  0.806
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1986)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.76
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.746
_refine_ls_goodness_of_fit_ref   1.881
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.115
_refine_ls_R_factor_gt           0.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00063|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.096
_refine_ls_wR_factor_ref         0.092
_reflns_number_gt                2435
_reflns_number_total             3011
_reflns_threshold_expression     I>0.70σ(I)
_cod_data_source_file            qa0186.cif
_cod_data_source_block           I
_cod_original_cell_volume        832.0(10)
_cod_database_code               2009313
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'  -x,  -y,  -z'
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_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
F 0.069 0.053
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N 0.029 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0.047 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S 0.319 0.557
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 2 0
0 4 0
1 3 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(1) S(1) O(2) 119.4(2) no
O(1) S(1) N(3) 107.0(2) no
O(1) S(1) C(15) 107.4(2) no
O(2) S(1) N(3) 107.4(2) no
O(2) S(1) C(15) 107.3(2) no
N(3) S(1) C(15) 107.9(2) no
N(2) N(1) C(1) 104.1(4) no
N(1) N(2) C(3) 112.6(4) no
N(1) N(2) C(12) 116.6(3) no
C(3) N(2) C(12) 130.5(4) no
S(1) N(3) H(13) 109(4) no
S(1) N(3) H(14) 117(4) no
H(13) N(3) H(14) 119(6) no
N(1) C(1) C(2) 112.3(4) no
N(1) C(1) C(4) 119.0(4) no
C(2) C(1) C(4) 128.6(4) no
C(1) C(2) C(3) 106.2(4) no
C(1) C(2) H(1) 126.8 no
C(3) C(2) H(1) 127.0 no
N(2) C(3) C(2) 104.8(4) no
N(2) C(3) C(5) 126.6(4) no
C(2) C(3) C(5) 128.6(4) no
F(1) C(4) F(2) 106.0(5) no
F(1) C(4) F(3) 106.0(5) no
F(1) C(4) C(1) 110.6(4) no
F(2) C(4) F(3) 107.7(4) no
F(2) C(4) C(1) 112.9(4) no
F(3) C(4) C(1) 113.2(5) no
C(3) C(5) C(6) 126.2(4) no
C(3) C(5) C(10) 117.3(4) no
C(6) C(5) C(10) 116.5(4) no
C(5) C(6) C(7) 121.9(5) no
C(5) C(6) H(2) 119.1 no
C(7) C(6) H(2) 119.0 no
C(6) C(7) C(8) 121.3(5) no
C(6) C(7) H(3) 119.6 no
C(8) C(7) H(3) 119.1 no
C(7) C(8) C(9) 117.3(5) no
C(7) C(8) C(11) 121.0(5) no
C(9) C(8) C(11) 121.6(5) no
C(8) C(9) C(10) 121.0(5) no
C(8) C(9) H(4) 118.7 no
C(10) C(9) H(4) 120.4 no
C(5) C(10) C(9) 122.0(5) no
C(5) C(10) H(5) 119.3 no
C(9) C(10) H(5) 118.7 no
C(8) C(11) H(6) 110.9 no
C(8) C(11) H(7) 109.7 no
C(8) C(11) H(8) 110.2 no
H(6) C(11) H(7) 108.7 no
H(6) C(11) H(8) 109.5 no
H(7) C(11) H(8) 107.7 no
N(2) C(12) C(13) 117.9(4) no
N(2) C(12) C(17) 120.0(4) no
C(13) C(12) C(17) 122.1(4) no
C(12) C(13) C(14) 119.2(4) no
C(12) C(13) H(9) 120.1 no
C(14) C(13) H(9) 120.7 no
C(13) C(14) C(15) 119.6(5) no
C(13) C(14) H(10) 120.6 no
C(15) C(14) H(10) 119.8 no
S(1) C(15) C(14) 119.1(4) no
S(1) C(15) C(16) 120.2(4) no
C(14) C(15) C(16) 120.7(4) no
C(15) C(16) C(17) 120.1(5) no
C(15) C(16) H(11) 119.8 no
C(17) C(16) H(11) 120.1 no
C(12) C(17) C(16) 118.3(5) no
C(12) C(17) H(12) 120.1 no
C(16) C(17) H(12) 121.6 no
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
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
F(1) C(10) 3.334(6) 2_767 no
F(1) C(2) 3.414(7) 1_556 no
F(1) C(9) 3.529(7) 2_767 no
F(2) N(3) 3.170(5) 2_757 no
F(2) N(2) 3.334(6) 1_556 no
F(2) N(1) 3.380(6) 1_556 no
F(2) O(2) 3.396(5) 2_756 no
F(2) C(3) 3.439(6) 1_556 no
F(2) C(1) 3.466(6) 1_556 no
F(2) C(2) 3.525(7) 1_556 no
F(3) C(7) 3.416(7) 1_656 no
F(3) N(3) 3.441(6) 2_756 no
F(3) C(11) 3.454(8) 1_656 no
F(3) C(11) 3.509(7) 1_657 no
F(3) C(8) 3.525(6) 1_656 no
O(1) C(14) 3.294(6) 2_656 no
O(1) C(13) 3.366(6) 2_656 no
O(1) C(15) 3.440(5) 2_655 no
O(1) C(14) 3.470(6) 2_655 no
O(1) O(1) 3.529(7) 2_655 no
O(1) C(7) 3.556(7) 2_655 no
O(1) C(6) 3.588(6) 2_655 no
O(2) N(3) 2.953(6) 1_554 no
O(2) C(14) 3.442(7) 1_554 no
N(1) N(3) 3.088(6) 2_756 no
N(1) C(17) 3.535(7) 1_556 no
C(2) C(10) 3.548(8) 1_556 no
C(13) C(16) 3.500(8) 1_556 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
S(1) C(15) C(14) C(13) -179.6(4) no
S(1) C(15) C(16) C(17) 179.9(4) no
F(1) C(4) C(1) N(1) -153.9(5) no
F(1) C(4) C(1) C(2) 30.0(8) no
F(2) C(4) C(1) N(1) -35.3(7) no
F(2) C(4) C(1) C(2) 148.5(5) no
F(3) C(4) C(1) N(1) 87.4(6) no
F(3) C(4) C(1) C(2) -88.8(6) no
O(1) S(1) C(15) C(14) 28.3(5) no
O(1) S(1) C(15) C(16) -152.2(4) no
O(2) S(1) C(15) C(14) 157.9(4) no
O(2) S(1) C(15) C(16) -22.6(5) no
N(1) N(2) C(3) C(2) -1.0(6) no
N(1) N(2) C(3) C(5) 176.6(4) no
N(1) N(2) C(12) C(13) 91.2(5) no
N(1) N(2) C(12) C(17) -86.7(6) no
N(1) C(1) C(2) C(3) -0.2(6) no
N(2) N(1) C(1) C(2) -0.4(6) no
N(2) N(1) C(1) C(4) -177.1(4) no
N(2) C(3) C(2) C(1) 0.7(5) no
N(2) C(3) C(5) C(6) 16.0(8) no
N(2) C(3) C(5) C(10) -163.4(5) no
N(2) C(12) C(13) C(14) -178.2(4) no
N(2) C(12) C(17) C(16) 178.5(5) no
N(3) S(1) C(15) C(14) -86.7(4) no
N(3) S(1) C(15) C(16) 92.8(4) no
C(1) N(1) N(2) C(3) 0.8(5) no
C(1) N(1) N(2) C(12) -174.7(4) no
C(1) C(2) C(3) C(5) -176.8(5) no
C(2) C(3) N(2) C(12) 173.8(5) no
C(2) C(3) C(5) C(6) -167.1(5) no
C(2) C(3) C(5) C(10) 13.6(8) no
C(3) N(2) C(12) C(13) -83.3(7) no
C(3) N(2) C(12) C(17) 98.8(6) no
C(3) C(2) C(1) C(4) 176.2(5) no
C(3) C(5) C(6) C(7) -179.7(5) no
C(3) C(5) C(10) C(9) 179.9979 no
C(5) C(3) N(2) C(12) -8.7(8) no
C(5) C(6) C(7) C(8) 1.8(9) no
C(5) C(10) C(9) C(8) -2.2(9) no
C(6) C(5) C(10) C(9) 0.6(8) no
C(6) C(7) C(8) C(9) -3.3(9) no
C(6) C(7) C(8) C(11) 178.5(6) no
C(7) C(6) C(5) C(10) -0.4(8) no
C(7) C(8) C(9) C(10) 3.5(9) no
C(10) C(9) C(8) C(11) -178.3(5) no
C(12) C(13) C(14) C(15) -0.5(8) no
C(12) C(17) C(16) C(15) -0.2(9) no
C(13) C(12) C(17) C(16) 0.7(8) no
C(13) C(14) C(15) C(16) 0.9(8) no
C(14) C(13) C(12) C(17) -0.4(8) no
C(14) C(15) C(16) C(17) -0.6(8) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2562
