#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:58:54 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257924 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157570.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_7157570
loop_
_publ_author_name
'Zhao, Jia-Hui'
'Zhou, Zhao-Zhao'
'Zhang, Yue'
'Su, Xuan'
'Chen, Xi-Meng'
'Liang, Yong-Min'
_publ_section_title
;
 Visible-light-mediated borylation of aryl and alkyl halides with a
 palladium complex.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4390
_journal_page_last               4394
_journal_paper_doi               10.1039/d0ob00028k
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_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 solvate'
_chemical_name_systematic
;
2-(3-cyano-4-isobutyloxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic 
acid ethanol solvate
;
_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
_audit_update_record
;
2020-05-04 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;
_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 Oxford Diffraction, 2015)'
_computing_data_collection
'CrysAlisPro (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction
'CrysAlisPro (Rigaku Oxford Diffraction, 2015)'
_computing_molecular_graphics
; 
XP/ShelXTL (Bruker-AXS, 1998) & Mercury (Macrae et al., 2008) 
;
_computing_publication_material
'PLATON (Spek, 2009) & publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/6 (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_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  '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_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_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_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.785
_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'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_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 Oxford Diffraction, 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_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack & Wagner, 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_Friedel_coverage         0.580
_reflns_Friedel_fraction_full    0.695
_reflns_Friedel_fraction_max     0.596
_reflns_number_gt                2917
_reflns_number_total             3070
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00028k2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7157503--7157570.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7157570
_publcif_datablock.id            {6678ffee-2fd8-4f1b-8a51-e4c39f09ceef}
_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
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32087(12) 0.17683(3) 0.31163(5) 0.02221(15) Uani 1 1 d . . . . .
C2 C 0.3894(5) 0.08540(14) 0.3610(2) 0.0195(5) Uani 1 1 d . . . . .
N3 N 0.2673(4) 0.06576(12) 0.45794(18) 0.0199(4) Uani 1 1 d . . . . .
C4 C 0.1127(5) 0.12385(14) 0.4979(2) 0.0210(5) Uani 1 1 d . . . . .
C5 C 0.1165(5) 0.18918(14) 0.4308(2) 0.0209(5) Uani 1 1 d . . . . .
C6 C 0.5737(5) 0.03525(14) 0.3007(2) 0.0188(5) Uani 1 1 d . . . . .
C7 C 0.6801(5) 0.05673(15) 0.1922(2) 0.0211(5) Uani 1 1 d . . . . .
H7 H 0.6309 0.1045 0.1555 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8571(5) 0.00904(14) 0.1371(2) 0.0208(5) Uani 1 1 d . . . . .
C9 C 0.9280(5) -0.06253(15) 0.1882(2) 0.0207(5) Uani 1 1 d . . . . .
C10 C 0.8252(5) -0.08344(15) 0.2980(2) 0.0231(5) Uani 1 1 d . . . . .
H10 H 0.8757 -0.1309 0.3357 0.028 Uiso 1 1 calc R U . . .
C11 C 0.6499(5) -0.03524(14) 0.3523(2) 0.0225(5) Uani 1 1 d . . . . .
H11 H 0.5797 -0.0505 0.4266 0.027 Uiso 1 1 calc R U . . .
C12 C -0.0406(5) 0.11107(16) 0.6073(2) 0.0269(6) Uani 1 1 d . . . . .
H12A H 0.0985 0.1093 0.6852 0.040 Uiso 1 1 calc R U . . .
H12B H -0.1448 0.0633 0.5962 0.040 Uiso 1 1 calc R U . . .
H12C H -0.1761 0.1522 0.6125 0.040 Uiso 1 1 calc R U . . .
C13 C -0.0224(5) 0.26111(15) 0.4499(2) 0.0234(5) Uani 1 1 d . . . . .
O14 O 0.0142(5) 0.31184(12) 0.36340(19) 0.0339(5) Uani 1 1 d D . . . .
H14 H -0.062(8) 0.3537(16) 0.375(4) 0.072(13) Uiso 1 1 d D . . . .
O15 O -0.1558(4) 0.27251(11) 0.53494(18) 0.0345(5) Uani 1 1 d . . . . .
C16 C 0.9755(6) 0.03373(15) 0.0278(2) 0.0259(6) Uani 1 1 d . . . . .
N17 N 1.0707(5) 0.05481(15) -0.0569(2) 0.0387(6) Uani 1 1 d . . . . .
O18 O 1.0943(4) -0.10584(10) 0.12590(16) 0.0248(4) Uani 1 1 d . . . . .
C19 C 1.1767(5) -0.17866(15) 0.1797(2) 0.0227(5) Uani 1 1 d . . . . .
H19A H 1.0042 -0.2076 0.1919 0.027 Uiso 1 1 calc R U . . .
H19B H 1.2988 -0.1724 0.2627 0.027 Uiso 1 1 calc R U . . .
C20 C 1.3396(5) -0.22023(14) 0.0906(2) 0.0236(5) Uani 1 1 d . . . . .
H20 H 1.4987 -0.1875 0.0709 0.028 Uiso 1 1 calc R U . . .
C21 C 1.4684(6) -0.29130(17) 0.1579(3) 0.0327(6) Uani 1 1 d . . . . .
H21A H 1.5817 -0.2775 0.2390 0.049 Uiso 1 1 calc R U . . .
H21B H 1.5919 -0.3164 0.1054 0.049 Uiso 1 1 calc R U . . .
H21C H 1.3139 -0.3254 0.1722 0.049 Uiso 1 1 calc R U . . .
C22 C 1.1480(7) -0.24066(17) -0.0320(3) 0.0336(6) Uani 1 1 d . . . . .
H22A H 1.0040 -0.2773 -0.0148 0.050 Uiso 1 1 calc R U . . .
H22B H 1.2643 -0.2625 -0.0907 0.050 Uiso 1 1 calc R U . . .
H22C H 1.0519 -0.1953 -0.0694 0.050 Uiso 1 1 calc R U . . .
O23 O 0.7299(4) 0.43799(11) 0.37730(18) 0.0347(5) Uani 1 1 d D . . . .
H23 H 0.741(8) 0.4681(18) 0.437(3) 0.053(11) Uiso 1 1 d D . . . .
C24 C 0.4973(6) 0.45692(16) 0.2805(3) 0.0347(7) Uani 1 1 d . . . . .
H24A H 0.5205 0.5091 0.2515 0.042 Uiso 1 1 calc R U . . .
H24B H 0.3143 0.4538 0.3142 0.042 Uiso 1 1 calc R U . . .
C25 C 0.4914(7) 0.40395(19) 0.1727(3) 0.0440(8) Uani 1 1 d . . . . .
H25A H 0.4835 0.3521 0.2031 0.066 Uiso 1 1 calc R U . . .
H25B H 0.6647 0.4107 0.1343 0.066 Uiso 1 1 calc R U . . .
H25C H 0.3222 0.4141 0.1097 0.066 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_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_distance
_geom_bond_site_symmetry_2
_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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O23 H23 N3 0.83(2) 2.07(2) 2.878(3) 162(4) 2_656
O14 H14 O23 0.84(2) 1.80(2) 2.631(3) 170(4) 1_455
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
?
