#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204976.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_2204976
loop_
_publ_author_name
'Yathirajan, Hemmige S.'
'Narasegowda, Rajenahally S.'
'Nagarajab, Padmarajaiah'
'Bolte, Michael'
_publ_section_title
;
 A pseudopolymorph of valdecoxib
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o179
_journal_page_last               o181
_journal_paper_doi               10.1107/S1600536804033598
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H14 N2 O3 S, 0.5C4 H8 O'
_chemical_formula_moiety         'C16 H14 N2 O3 S, 0.5C4 H8 O'
_chemical_formula_sum            'C18 H18 N2 O3.5 S'
_chemical_formula_weight         350.40
_chemical_name_systematic
;
4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide ethyl methyl ketone
hemisolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 94.373(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0201(14)
_cell_length_b                   7.7930(5)
_cell_length_c                   17.3305(19)
_cell_measurement_reflns_used    24673
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      3.5
_cell_volume                     1753.3(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'STOE IPDS-II two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24057
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.8
_diffrn_reflns_theta_min         3.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 1990; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.56
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0755P)²+0.4033P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.126
_refine_ls_wR_factor_ref         0.131
_reflns_number_gt                2768
_reflns_number_total             3345
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6204.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204976
_cod_database_fobs_code          2204976
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 0.06511(3) 0.75708(5) 0.22545(2) 0.02823(16) Uani d . 1 . . S
N1 -0.04516(12) 0.7592(2) 0.26081(11) 0.0339(4) Uani d . 1 . . N
H1A -0.0598(17) 0.667(3) 0.2835(13) 0.037(6) Uiso d . 1 . . H
H1B -0.053(2) 0.843(4) 0.2872(15) 0.052(7) Uiso d . 1 . . H
O11 0.07021(10) 0.60084(16) 0.18285(7) 0.0356(3) Uani d . 1 . . O
O12 0.07531(10) 0.91506(16) 0.18463(7) 0.0336(3) Uani d . 1 . . O
C1 0.40159(14) 0.7225(2) 0.48139(10) 0.0300(4) Uani d . 1 . . C
C2 0.50930(14) 0.7445(2) 0.47417(11) 0.0328(4) Uani d . 1 . . C
N3 0.56210(14) 0.7312(2) 0.54123(10) 0.0434(4) Uani d . 1 . . N
O4 0.48920(12) 0.7000(2) 0.59505(8) 0.0451(4) Uani d . 1 . . O
C5 0.39420(15) 0.6941(3) 0.55751(11) 0.0374(4) Uani d . 1 . . C
C51 0.30683(19) 0.6607(3) 0.60542(12) 0.0512(5) Uani d . 1 . . C
H51A 0.2428 0.7019 0.5781 0.077 Uiso calc R 1 . . H
H51B 0.3184 0.7211 0.6549 0.077 Uiso calc R 1 . . H
H51C 0.3015 0.5372 0.6149 0.077 Uiso calc R 1 . . H
C11 0.31684(13) 0.7340(2) 0.42022(10) 0.0292(4) Uani d . 1 . . C
C12 0.30512(14) 0.8795(2) 0.37443(11) 0.0339(4) Uani d . 1 . . C
H12 0.3504 0.9741 0.3840 0.041 Uiso calc R 1 . . H
C13 0.22815(13) 0.8884(2) 0.31496(10) 0.0317(4) Uani d . 1 . . C
H13 0.2208 0.9878 0.2833 0.038 Uiso calc R 1 . . H
C14 0.16212(13) 0.7510(2) 0.30212(10) 0.0278(4) Uani d . 1 . . C
C15 0.17113(14) 0.6062(2) 0.34832(11) 0.0349(4) Uani d . 1 . . C
H15 0.1243 0.5134 0.3398 0.042 Uiso calc R 1 . . H
C16 0.24890(14) 0.5982(2) 0.40694(11) 0.0339(4) Uani d . 1 . . C
H16 0.2560 0.4987 0.4385 0.041 Uiso calc R 1 . . H
C21 0.56250(15) 0.7697(2) 0.40305(13) 0.0381(4) Uani d . 1 . . C
C22 0.65232(17) 0.8662(3) 0.40405(18) 0.0588(7) Uani d . 1 . . C
H22 0.6798 0.9193 0.4505 0.071 Uiso calc R 1 . . H
C23 0.7015(2) 0.8839(4) 0.3357(3) 0.0876(12) Uani d . 1 . . C
H23 0.7623 0.9513 0.3358 0.105 Uiso calc R 1 . . H
C24 0.6641(3) 0.8065(4) 0.2689(2) 0.0806(11) Uani d . 1 . . C
H24 0.6989 0.8197 0.2230 0.097 Uiso calc R 1 . . H
C25 0.5761(2) 0.7094(4) 0.26801(15) 0.0633(7) Uani d . 1 . . C
H25 0.5504 0.6547 0.2215 0.076 Uiso calc R 1 . . H
C26 0.52496(14) 0.6907(3) 0.33418(10) 0.0439(5) Uani d . 1 . . C
H26 0.4639 0.6238 0.3330 0.053 Uiso calc R 1 . . H
O1L 0.11783(14) 0.9379(3) 0.49816(10) 0.1092(18) Uani d PR 0.50 . 1 O
C1L 0.04893(14) 0.4843(3) -0.00214(10) 0.253(6) Uani d R 1 . . C
H1LA 0.0904 0.9672 0.5397 0.303 Uiso d PR 0.50 A 2 H
H1LB 0.0731 0.9823 0.4496 0.303 Uiso d PR 0.50 B 2 H
C2L 0.0467(5) 0.2365(7) 0.5065(3) 0.138(2) Uani d . 1 . . C
H2LA 0.1155 1.2793 0.5044 0.207 Uiso d R 1 . . H
H2LB 0.0034 1.2840 0.4645 0.207 Uiso d R 1 . . H
H2LC 0.0207 1.2689 0.5547 0.207 Uiso d R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O11 S1 O12 . . 117.92(8)
O11 S1 N1 . . 106.54(9)
O12 S1 N1 . . 107.43(8)
O11 S1 C14 . . 107.93(8)
O12 S1 C14 . . 107.92(8)
N1 S1 C14 . . 108.85(9)
S1 N1 H1A . . 114.0(15)
S1 N1 H1B . . 111.9(19)
H1A N1 H1B . . 113(2)
C5 C1 C2 . . 104.43(16)
C5 C1 C11 . . 127.49(17)
C2 C1 C11 . . 128.05(16)
N3 C2 C1 . . 111.46(17)
N3 C2 C21 . . 120.34(18)
C1 C2 C21 . . 128.12(17)
C2 N3 O4 . . 105.55(16)
C5 O4 N3 . . 109.05(14)
C1 C5 O4 . . 109.51(17)
C1 C5 C51 . . 133.80(19)
O4 C5 C51 . . 116.69(17)
C5 C51 H51A . . 109.5
C5 C51 H51B . . 109.5
H51A C51 H51B . . 109.5
C5 C51 H51C . . 109.5
H51A C51 H51C . . 109.5
H51B C51 H51C . . 109.5
C16 C11 C12 . . 119.22(16)
C16 C11 C1 . . 120.39(16)
C12 C11 C1 . . 120.38(16)
C13 C12 C11 . . 120.61(17)
C13 C12 H12 . . 119.7
C11 C12 H12 . . 119.7
C14 C13 C12 . . 119.24(16)
C14 C13 H13 . . 120.4
C12 C13 H13 . . 120.4
C13 C14 C15 . . 121.00(16)
C13 C14 S1 . . 120.14(13)
C15 C14 S1 . . 118.85(13)
C16 C15 C14 . . 119.20(17)
C16 C15 H15 . . 120.4
C14 C15 H15 . . 120.4
C15 C16 C11 . . 120.71(17)
C15 C16 H16 . . 119.6
C11 C16 H16 . . 119.6
C22 C21 C26 . . 119.2(2)
C22 C21 C2 . . 120.7(2)
C26 C21 C2 . . 119.98(17)
C21 C22 C23 . . 118.9(3)
C21 C22 H22 . . 120.6
C23 C22 H22 . . 120.6
C24 C23 C22 . . 121.4(3)
C24 C23 H23 . . 119.3
C22 C23 H23 . . 119.3
C23 C24 C25 . . 119.8(3)
C23 C24 H24 . . 120.1
C25 C24 H24 . . 120.1
C24 C25 C26 . . 120.4(3)
C24 C25 H25 . . 119.8
C26 C25 H25 . . 119.8
C25 C26 C21 . . 120.3(2)
C25 C26 H26 . . 119.8
C21 C26 H26 . . 119.8
C1L O1L H1LA 4_576 . 57.2
C1L O1L H1LB 4_576 . 53.1
H1LA O1L H1LB . . 110.2
O1L C1L C1L 4_575 3_565 134.9(4)
O1L C1L C2L 4_575 4_565 125.3(3)
C1L C1L C2L 3_565 4_565 99.2(3)
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
S1 O11 . 1.4280(13) y
S1 O12 . 1.4311(13) y
S1 N1 . 1.6036(18) y
S1 C14 . 1.7628(18) y
N1 H1A . 0.85(3) ?
N1 H1B . 0.81(3) ?
C1 C5 . 1.348(3) y
C1 C2 . 1.428(3) y
C1 C11 . 1.473(2) ?
C2 N3 . 1.309(3) y
C2 C21 . 1.472(3) ?
N3 O4 . 1.402(2) y
O4 C5 . 1.354(2) y
C5 C51 . 1.482(3) ?
C51 H51A . 0.9800 ?
C51 H51B . 0.9800 ?
C51 H51C . 0.9800 ?
C11 C16 . 1.387(3) ?
C11 C12 . 1.386(3) ?
C12 C13 . 1.383(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.380(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.383(2) ?
C15 C16 . 1.380(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.389(3) ?
C21 C26 . 1.398(3) ?
C22 C23 . 1.395(5) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.363(6) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.372(5) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.377(3) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
O1L C1L 4_576 1.083(2) ?
O1L H1LA . 0.8593 ?
O1L H1LB . 1.0461 ?
C1L O1L 4_575 1.083(2) ?
C1L C1L 3_565 1.305(4) ?
C1L C2L 4_565 1.727(6) ?
C2L C1L 4_566 1.727(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O12 2_545 0.85(3) 2.05(3) 2.881(2) 165(2)
N1 H1B O11 2 0.81(3) 2.09(3) 2.863(2) 160(3)
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
C5 C1 C2 N3 -0.4(2)
C11 C1 C2 N3 177.69(18)
C5 C1 C2 C21 176.34(18)
C11 C1 C2 C21 -5.6(3)
C1 C2 N3 O4 -0.1(2)
C21 C2 N3 O4 -177.13(16)
C2 N3 O4 C5 0.6(2)
C2 C1 C5 O4 0.8(2)
C11 C1 C5 O4 -177.35(17)
C2 C1 C5 C51 -179.8(2)
C11 C1 C5 C51 2.1(4)
N3 O4 C5 C1 -0.9(2)
N3 O4 C5 C51 179.58(18)
C5 C1 C11 C16 -58.0(3)
C2 C1 C11 C16 124.4(2)
C5 C1 C11 C12 123.1(2)
C2 C1 C11 C12 -54.5(3)
C16 C11 C12 C13 -1.5(3)
C1 C11 C12 C13 177.46(17)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C15 0.8(3)
C12 C13 C14 S1 -178.65(14)
O11 S1 C14 C13 130.75(15)
O12 S1 C14 C13 2.30(17)
N1 S1 C14 C13 -114.00(15)
O11 S1 C14 C15 -48.70(16)
O12 S1 C14 C15 -177.15(14)
N1 S1 C14 C15 66.55(16)
C13 C14 C15 C16 -1.5(3)
S1 C14 C15 C16 177.99(15)
C14 C15 C16 C11 0.7(3)
C12 C11 C16 C15 0.8(3)
C1 C11 C16 C15 -178.15(17)
N3 C2 C21 C22 -34.5(3)
C1 C2 C21 C22 149.0(2)
N3 C2 C21 C26 143.0(2)
C1 C2 C21 C26 -33.5(3)
C26 C21 C22 C23 1.1(3)
C2 C21 C22 C23 178.6(2)
C21 C22 C23 C24 -1.1(4)
C22 C23 C24 C25 0.3(5)
C23 C24 C25 C26 0.5(4)
C24 C25 C26 C21 -0.4(4)
C22 C21 C26 C25 -0.4(3)
C2 C21 C26 C25 -177.97(19)
