#------------------------------------------------------------------------------
#$Date: 2020-05-13 07:56:36 +0300 (Wed, 13 May 2020) $
#$Revision: 252015 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243387.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_2243387
loop_
_publ_author_name
'Gelbrich, Thomas'
'Kahlenberg, Volker'
'Adamer, Verena'
'Nerdinger, Sven'
'Griesser, Ulrich J.'
_publ_section_title
;
 Febuxostat ethanol monosolvate
;
_journal_coeditor_code           FY2145
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              816
_journal_page_last               819
_journal_paper_doi               10.1107/S2056989020006076
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C16 H16 N2 O3 S, C2 H6 O'
_chemical_formula_moiety         'C16 H16 N2 O3 S, C2 H6 O'
_chemical_formula_sum            'C18 H22 N2 O4 S'
_chemical_formula_weight         362.43
_chemical_name_common            'febuxostat ethanol monosolvate'
_chemical_name_systematic
;
2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic
acid ethanol monosolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 98.994(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7274(2)
_cell_length_b                   17.7820(5)
_cell_length_c                   10.7340(4)
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.6190
_cell_measurement_theta_min      2.2480
_cell_volume                     891.23(6)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
XP in ShelXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2020)
;
_computing_publication_material
;
PLATON (Spek, 2020) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/6 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6054
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.094
_diffrn_reflns_theta_min         1.921
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro (Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.360
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.171
_refine_ls_abs_structure_details
;
Flack x determined using 1046 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0439P)²+0.0696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                2917
_reflns_number_total             3070
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fy2145sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243387
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.922
_shelx_estimated_absorpt_t_max   0.929
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.32087(12) 0.17683(3) 0.31163(5) 0.02221(15) Uani d 1 . .
C C2 0.3894(5) 0.08540(14) 0.3610(2) 0.0195(5) Uani d 1 . .
N N3 0.2673(4) 0.06576(12) 0.45794(18) 0.0199(4) Uani d 1 . .
C C4 0.1127(5) 0.12385(14) 0.4979(2) 0.0210(5) Uani d 1 . .
C C5 0.1165(5) 0.18918(14) 0.4308(2) 0.0209(5) Uani d 1 . .
C C6 0.5737(5) 0.03525(14) 0.3007(2) 0.0188(5) Uani d 1 . .
C C7 0.6801(5) 0.05673(15) 0.1922(2) 0.0211(5) Uani d 1 . .
H H7 0.6309 0.1045 0.1555 0.025 Uiso calc 1 . .
C C8 0.8571(5) 0.00904(14) 0.1371(2) 0.0208(5) Uani d 1 . .
C C9 0.9280(5) -0.06253(15) 0.1882(2) 0.0207(5) Uani d 1 . .
C C10 0.8252(5) -0.08344(15) 0.2980(2) 0.0231(5) Uani d 1 . .
H H10 0.8757 -0.1309 0.3357 0.028 Uiso calc 1 . .
C C11 0.6499(5) -0.03524(14) 0.3523(2) 0.0225(5) Uani d 1 . .
H H11 0.5797 -0.0505 0.4266 0.027 Uiso calc 1 . .
C C12 -0.0406(5) 0.11107(16) 0.6073(2) 0.0269(6) Uani d 1 . .
H H12A 0.0985 0.1093 0.6852 0.040 Uiso calc 1 . .
H H12B -0.1448 0.0633 0.5962 0.040 Uiso calc 1 . .
H H12C -0.1761 0.1522 0.6125 0.040 Uiso calc 1 . .
C C13 -0.0224(5) 0.26111(15) 0.4499(2) 0.0234(5) Uani d 1 . .
O O14 0.0142(5) 0.31184(12) 0.36340(19) 0.0339(5) Uani d 1 . .
H H14 -0.062(8) 0.3537(16) 0.375(4) 0.072(13) Uiso d 1 . .
O O15 -0.1558(4) 0.27251(11) 0.53494(18) 0.0345(5) Uani d 1 . .
C C16 0.9755(6) 0.03373(15) 0.0278(2) 0.0259(6) Uani d 1 . .
N N17 1.0707(5) 0.05481(15) -0.0569(2) 0.0387(6) Uani d 1 . .
O O18 1.0943(4) -0.10584(10) 0.12590(16) 0.0248(4) Uani d 1 . .
C C19 1.1767(5) -0.17866(15) 0.1797(2) 0.0227(5) Uani d 1 . .
H H19A 1.0042 -0.2076 0.1919 0.027 Uiso calc 1 . .
H H19B 1.2988 -0.1724 0.2627 0.027 Uiso calc 1 . .
C C20 1.3396(5) -0.22023(14) 0.0906(2) 0.0236(5) Uani d 1 . .
H H20 1.4987 -0.1875 0.0709 0.028 Uiso calc 1 . .
C C21 1.4684(6) -0.29130(17) 0.1579(3) 0.0327(6) Uani d 1 . .
H H21A 1.5817 -0.2775 0.2390 0.049 Uiso calc 1 . .
H H21B 1.5919 -0.3164 0.1054 0.049 Uiso calc 1 . .
H H21C 1.3139 -0.3254 0.1722 0.049 Uiso calc 1 . .
C C22 1.1480(7) -0.24066(17) -0.0320(3) 0.0336(6) Uani d 1 . .
H H22A 1.0040 -0.2773 -0.0148 0.050 Uiso calc 1 . .
H H22B 1.2643 -0.2625 -0.0907 0.050 Uiso calc 1 . .
H H22C 1.0519 -0.1953 -0.0694 0.050 Uiso calc 1 . .
O O23 0.7299(4) 0.43799(11) 0.37730(18) 0.0347(5) Uani d 1 . .
H H23 0.741(8) 0.4681(18) 0.437(3) 0.053(11) Uiso d 1 . .
C C24 0.4973(6) 0.45692(16) 0.2805(3) 0.0347(7) Uani d 1 . .
H H24A 0.5205 0.5091 0.2515 0.042 Uiso calc 1 . .
H H24B 0.3143 0.4538 0.3142 0.042 Uiso calc 1 . .
C C25 0.4914(7) 0.40395(19) 0.1727(3) 0.0440(8) Uani d 1 . .
H H25A 0.4835 0.3521 0.2031 0.066 Uiso calc 1 . .
H H25B 0.6647 0.4107 0.1343 0.066 Uiso calc 1 . .
H H25C 0.3222 0.4141 0.1097 0.066 Uiso calc 1 . .
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
_geom_angle_publ_flag
C2 S1 C5 . . 89.55(12) ?
N3 C2 C6 . . 123.6(2) ?
N3 C2 S1 . . 114.17(18) ?
C6 C2 S1 . . 122.25(18) ?
C2 N3 C4 . . 111.7(2) ?
C5 C4 N3 . . 115.0(2) ?
C5 C4 C12 . . 126.3(2) ?
N3 C4 C12 . . 118.7(2) ?
C4 C5 C13 . . 128.6(2) ?
C4 C5 S1 . . 109.62(19) ?
C13 C5 S1 . . 121.80(19) ?
C7 C6 C11 . . 118.3(2) ?
C7 C6 C2 . . 121.3(2) ?
C11 C6 C2 . . 120.4(2) ?
C8 C7 C6 . . 120.7(2) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C9 . . 120.6(2) ?
C7 C8 C16 . . 119.8(2) ?
C9 C8 C16 . . 119.6(2) ?
O18 C9 C10 . . 125.0(2) ?
O18 C9 C8 . . 116.4(2) ?
C10 C9 C8 . . 118.6(2) ?
C11 C10 C9 . . 120.1(2) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C6 . . 121.6(2) ?
C10 C11 H11 . . 119.2 ?
C6 C11 H11 . . 119.2 ?
C4 C12 H12A . . 109.5 ?
C4 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C4 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O15 C13 O14 . . 123.9(2) ?
O15 C13 C5 . . 123.5(2) ?
O14 C13 C5 . . 112.7(2) ?
C13 O14 H14 . . 113(3) ?
N17 C16 C8 . . 178.3(3) ?
C9 O18 C19 . . 117.03(18) ?
O18 C19 C20 . . 108.51(19) ?
O18 C19 H19A . . 110.0 ?
C20 C19 H19A . . 110.0 ?
O18 C19 H19B . . 110.0 ?
C20 C19 H19B . . 110.0 ?
H19A C19 H19B . . 108.4 ?
C19 C20 C22 . . 111.8(2) ?
C19 C20 C21 . . 108.0(2) ?
C22 C20 C21 . . 110.5(2) ?
C19 C20 H20 . . 108.9 ?
C22 C20 H20 . . 108.9 ?
C21 C20 H20 . . 108.9 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C24 O23 H23 . . 111(3) ?
O23 C24 C25 . . 109.5(2) ?
O23 C24 H24A . . 109.8 ?
C25 C24 H24A . . 109.8 ?
O23 C24 H24B . . 109.8 ?
C25 C24 H24B . . 109.8 ?
H24A C24 H24B . . 108.2 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
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 C2 . 1.725(3) ?
S1 C5 . 1.733(2) ?
C2 N3 . 1.313(3) ?
C2 C6 . 1.466(3) ?
N3 C4 . 1.372(3) ?
C4 C5 . 1.369(4) ?
C4 C12 . 1.491(3) ?
C5 C13 . 1.467(4) ?
C6 C7 . 1.393(3) ?
C6 C11 . 1.395(3) ?
C7 C8 . 1.387(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.406(4) ?
C8 C16 . 1.444(4) ?
C9 O18 . 1.350(3) ?
C9 C10 . 1.394(3) ?
C10 C11 . 1.383(4) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 O15 . 1.205(3) ?
C13 O14 . 1.325(3) ?
O14 H14 . 0.84(2) ?
C16 N17 . 1.139(3) ?
O18 C19 . 1.446(3) ?
C19 C20 . 1.511(3) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C22 . 1.520(4) ?
C20 C21 . 1.534(4) ?
C20 H20 . 1.0000 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
O23 C24 . 1.430(4) ?
O23 H23 . 0.83(2) ?
C24 C25 . 1.489(4) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
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
O23 H23 N3 2_656 0.83(2) 2.07(2) 2.878(3) 162(4)
O14 H14 O23 1_455 0.84(2) 1.80(2) 2.631(3) 170(4)

_cod_database_fobs_code 2243387
