#------------------------------------------------------------------------------
#$Date: 2024-11-09 04:46:57 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295854 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/33/2023314.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_2023314
loop_
_publ_author_name
'Mohan Kumar, Thaluru M.'
'Bhaskar, Besagarahally L.'
'Priyanka, Prabhakar'
'Divakara, Thayamma R.'
'Yathirajan, Hemmige S.'
'Parkin, Sean'
_publ_section_title
;
 Crystal structure and Hirshfeld-surface analysis of an etoxazole
 metabolite designated R13
;
_journal_coeditor_code           NX2015
_journal_issue                   12
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024010600
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C21 H21 F2 N O2'
_chemical_formula_moiety         'C21 H21 F2 N O2'
_chemical_formula_sum            'C21 H21 F2 N O2'
_chemical_formula_weight         357.39
_chemical_name_systematic
;
4-(4-tert-Butyl-2-ethoxyphenyl)-2-(2,6-difluorophenyl)oxazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 93.0350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.4793(6)
_cell_length_b                   10.4036(3)
_cell_length_c                   18.5669(7)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.25
_cell_volume                     3564.5(2)
_computing_cell_refinement
;
APEX5 (Bruker, 2023)
;
_computing_data_collection
;
APEX5 (Bruker, 2023)
;
_computing_data_reduction
;
APEX5 (Bruker, 2023)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and publCIF (Westrip,
2010)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41370
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.197
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0325
_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)+(0.0317P)²+1.7737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                3558
_reflns_number_total             4095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nx2015.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2023314
_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   0.980
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
F F1 0.31274(3) 0.82135(6) 0.32509(3) 0.02734(16) Uani d 1 . .
F F2 0.05890(3) 0.81737(7) 0.34205(4) 0.03608(19) Uani d 1 . .
O O1 0.14316(4) 0.71474(7) 0.44635(4) 0.02199(17) Uani d 1 . .
O O2 0.19533(4) 0.41164(7) 0.58364(4) 0.02220(17) Uani d 1 . .
N N1 0.24848(5) 0.64149(8) 0.41010(5) 0.02001(18) Uani d 1 . .
C C1 0.19516(5) 0.72003(9) 0.39718(5) 0.0190(2) Uani d 1 . .
C C2 0.16811(6) 0.62314(10) 0.49472(6) 0.0216(2) Uani d 1 . .
H H2 0.144270 0.596124 0.536213 0.026 Uiso calc 1 . .
C C3 0.23218(5) 0.57765(9) 0.47364(5) 0.0189(2) Uani d 1 . .
C C4 0.28343(5) 0.48460(9) 0.50675(5) 0.0190(2) Uani d 1 . .
C C5 0.35428(6) 0.47979(10) 0.48489(6) 0.0216(2) Uani d 1 . .
H H5 0.368284 0.535977 0.447771 0.026 Uiso calc 1 . .
C C6 0.40484(6) 0.39551(10) 0.51568(6) 0.0229(2) Uani d 1 . .
H H6 0.452820 0.395248 0.499675 0.028 Uiso calc 1 . .
C C7 0.38619(5) 0.31068(9) 0.57009(5) 0.0196(2) Uani d 1 . .
C C8 0.31520(5) 0.31386(9) 0.59192(5) 0.0197(2) Uani d 1 . .
H H8 0.301032 0.255850 0.628094 0.024 Uiso calc 1 . .
C C9 0.26455(5) 0.40030(9) 0.56181(5) 0.0190(2) Uani d 1 . .
C C10 0.17146(6) 0.32330(10) 0.63687(6) 0.0222(2) Uani d 1 . .
H H10A 0.205099 0.324699 0.680171 0.027 Uiso calc 1 . .
H H10B 0.169803 0.234787 0.617268 0.027 Uiso calc 1 . .
C C11 0.09681(6) 0.36551(12) 0.65605(6) 0.0294(3) Uani d 1 . .
H H11A 0.063603 0.360211 0.613215 0.044 Uiso calc 1 . .
H H11B 0.098855 0.454391 0.673527 0.044 Uiso calc 1 . .
H H11C 0.079477 0.309378 0.693857 0.044 Uiso calc 1 . .
C C12 0.44366(5) 0.22003(10) 0.60412(6) 0.0216(2) Uani d 1 . .
C C13 0.41297(6) 0.12946(11) 0.65984(6) 0.0283(2) Uani d 1 . .
H H13A 0.373991 0.077640 0.636764 0.043 Uiso calc 1 . .
H H13B 0.393756 0.180052 0.699046 0.043 Uiso calc 1 . .
H H13C 0.451514 0.072699 0.679385 0.043 Uiso calc 1 . .
C C14 0.50460(6) 0.30006(12) 0.64139(7) 0.0315(3) Uani d 1 . .
H H14A 0.525169 0.357895 0.606173 0.047 Uiso calc 1 . .
H H14B 0.542537 0.242579 0.661459 0.047 Uiso calc 1 . .
H H14C 0.484974 0.350789 0.680327 0.047 Uiso calc 1 . .
C C15 0.47507(6) 0.13723(11) 0.54504(6) 0.0282(2) Uani d 1 . .
H H15A 0.435806 0.090190 0.519134 0.042 Uiso calc 1 . .
H H15B 0.509964 0.075983 0.567013 0.042 Uiso calc 1 . .
H H15C 0.499521 0.192584 0.511211 0.042 Uiso calc 1 . .
C C16 0.18637(5) 0.81374(9) 0.33852(5) 0.0192(2) Uani d 1 . .
C C17 0.24577(5) 0.86239(10) 0.30370(5) 0.0203(2) Uani d 1 . .
C C18 0.23993(6) 0.95121(10) 0.24873(6) 0.0227(2) Uani d 1 . .
H H18 0.281992 0.981741 0.226916 0.027 Uiso calc 1 . .
C C19 0.17194(6) 0.99543(10) 0.22567(6) 0.0241(2) Uani d 1 . .
H H19 0.167056 1.057008 0.187945 0.029 Uiso calc 1 . .
C C20 0.11108(6) 0.94965(11) 0.25776(6) 0.0264(2) Uani d 1 . .
H H20 0.064166 0.978656 0.241898 0.032 Uiso calc 1 . .
C C21 0.11937(6) 0.86175(10) 0.31282(6) 0.0237(2) Uani d 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'
F F 0.0171 0.0103 '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'
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
C1 O1 C2 . . 104.02(8) ?
C9 O2 C10 . . 118.37(8) ?
C1 N1 C3 . . 105.08(8) ?
N1 C1 O1 . . 114.10(9) ?
N1 C1 C16 . . 127.75(9) ?
O1 C1 C16 . . 118.12(9) ?
C3 C2 O1 . . 108.82(9) ?
C3 C2 H2 . . 125.6 ?
O1 C2 H2 . . 125.6 ?
C2 C3 N1 . . 107.97(9) ?
C2 C3 C4 . . 131.74(9) ?
N1 C3 C4 . . 120.22(9) ?
C5 C4 C9 . . 117.61(9) ?
C5 C4 C3 . . 119.87(9) ?
C9 C4 C3 . . 122.51(9) ?
C6 C5 C4 . . 121.84(10) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C5 C6 C7 . . 120.80(10) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C8 C7 C6 . . 117.83(9) ?
C8 C7 C12 . . 122.52(9) ?
C6 C7 C12 . . 119.65(9) ?
C9 C8 C7 . . 121.41(9) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
O2 C9 C8 . . 123.77(9) ?
O2 C9 C4 . . 115.73(9) ?
C8 C9 C4 . . 120.49(9) ?
O2 C10 C11 . . 107.11(8) ?
O2 C10 H10A . . 110.3 ?
C11 C10 H10A . . 110.3 ?
O2 C10 H10B . . 110.3 ?
C11 C10 H10B . . 110.3 ?
H10A C10 H10B . . 108.5 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C7 . . 112.60(8) ?
C13 C12 C15 . . 107.80(9) ?
C7 C12 C15 . . 109.36(8) ?
C13 C12 C14 . . 108.56(9) ?
C7 C12 C14 . . 109.15(9) ?
C15 C12 C14 . . 109.32(9) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C21 C16 C17 . . 114.61(9) ?
C21 C16 C1 . . 123.64(9) ?
C17 C16 C1 . . 121.75(9) ?
F1 C17 C18 . . 117.73(9) ?
F1 C17 C16 . . 118.68(9) ?
C18 C17 C16 . . 123.59(10) ?
C17 C18 C19 . . 119.12(10) ?
C17 C18 H18 . . 120.4 ?
C19 C18 H18 . . 120.4 ?
C18 C19 C20 . . 119.80(10) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C21 C20 C19 . . 119.20(10) ?
C21 C20 H20 . . 120.4 ?
C19 C20 H20 . . 120.4 ?
F2 C21 C20 . . 117.70(9) ?
F2 C21 C16 . . 118.60(9) ?
C20 C21 C16 . . 123.68(10) ?
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
F1 C17 . 1.3489(12) ?
F2 C21 . 1.3495(12) ?
O1 C1 . 1.3611(12) ?
O1 C2 . 1.3725(12) ?
O2 C9 . 1.3671(12) ?
O2 C10 . 1.4361(12) ?
N1 C1 . 1.2927(13) ?
N1 C3 . 1.4004(13) ?
C1 C16 . 1.4644(14) ?
C2 C3 . 1.3521(14) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.4664(14) ?
C4 C5 . 1.3919(14) ?
C4 C9 . 1.4049(14) ?
C5 C6 . 1.3827(15) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.3983(14) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3938(14) ?
C7 C12 . 1.5314(14) ?
C8 C9 . 1.3934(14) ?
C8 H8 . 0.9500 ?
C10 C11 . 1.5081(15) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C13 . 1.5303(15) ?
C12 C15 . 1.5328(15) ?
C12 C14 . 1.5355(15) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C21 . 1.3955(15) ?
C16 C17 . 1.3978(14) ?
C17 C18 . 1.3768(14) ?
C18 C19 . 1.3843(15) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.3848(16) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.3741(15) ?
C20 H20 . 0.9500 ?
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
_geom_hbond_publ_flag
C2 H2 O2 . 0.95 2.29 2.7807(12) 111.1 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C1 O1 . . . . -0.50(11) ?
C3 N1 C1 C16 . . . . 177.39(9) ?
C2 O1 C1 N1 . . . . 0.39(11) ?
C2 O1 C1 C16 . . . . -177.71(9) ?
C1 O1 C2 C3 . . . . -0.11(11) ?
O1 C2 C3 N1 . . . . -0.18(11) ?
O1 C2 C3 C4 . . . . 176.69(10) ?
C1 N1 C3 C2 . . . . 0.40(11) ?
C1 N1 C3 C4 . . . . -176.89(9) ?
C2 C3 C4 C5 . . . . -162.47(11) ?
N1 C3 C4 C5 . . . . 14.08(14) ?
C2 C3 C4 C9 . . . . 15.99(17) ?
N1 C3 C4 C9 . . . . -167.46(9) ?
C9 C4 C5 C6 . . . . 0.07(15) ?
C3 C4 C5 C6 . . . . 178.60(9) ?
C4 C5 C6 C7 . . . . 0.45(16) ?
C5 C6 C7 C8 . . . . 0.16(15) ?
C5 C6 C7 C12 . . . . -178.95(9) ?
C6 C7 C8 C9 . . . . -1.30(15) ?
C12 C7 C8 C9 . . . . 177.78(9) ?
C10 O2 C9 C8 . . . . -4.80(14) ?
C10 O2 C9 C4 . . . . 176.53(9) ?
C7 C8 C9 O2 . . . . -176.75(9) ?
C7 C8 C9 C4 . . . . 1.86(15) ?
C5 C4 C9 O2 . . . . 177.51(9) ?
C3 C4 C9 O2 . . . . -0.98(14) ?
C5 C4 C9 C8 . . . . -1.20(14) ?
C3 C4 C9 C8 . . . . -179.69(9) ?
C9 O2 C10 C11 . . . . 174.49(9) ?
C8 C7 C12 C13 . . . . 3.86(14) ?
C6 C7 C12 C13 . . . . -177.08(9) ?
C8 C7 C12 C15 . . . . 123.67(10) ?
C6 C7 C12 C15 . . . . -57.26(12) ?
C8 C7 C12 C14 . . . . -116.78(11) ?
C6 C7 C12 C14 . . . . 62.29(12) ?
N1 C1 C16 C21 . . . . 156.63(11) ?
O1 C1 C16 C21 . . . . -25.56(14) ?
N1 C1 C16 C17 . . . . -23.42(16) ?
O1 C1 C16 C17 . . . . 154.39(9) ?
C21 C16 C17 F1 . . . . 179.95(9) ?
C1 C16 C17 F1 . . . . -0.01(14) ?
C21 C16 C17 C18 . . . . 0.45(15) ?
C1 C16 C17 C18 . . . . -179.51(9) ?
F1 C17 C18 C19 . . . . -179.85(9) ?
C16 C17 C18 C19 . . . . -0.35(16) ?
C17 C18 C19 C20 . . . . -0.28(16) ?
C18 C19 C20 C21 . . . . 0.77(16) ?
C19 C20 C21 F2 . . . . -178.85(10) ?
C19 C20 C21 C16 . . . . -0.67(17) ?
C17 C16 C21 F2 . . . . 178.24(9) ?
C1 C16 C21 F2 . . . . -1.81(16) ?
C17 C16 C21 C20 . . . . 0.07(16) ?
C1 C16 C21 C20 . . . . -179.98(10) ?
