#------------------------------------------------------------------------------
#$Date: 2022-05-18 04:43:58 +0300 (Wed, 18 May 2022) $
#$Revision: 275503 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244095.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_2244095
loop_
_publ_author_name
'Khrustalev, Victor N.'
'Çelikesir, Sevim Türktekin'
'Akkurt, Mehmet'
'Kolesnik, Irina A.'
'Potkin, Vladimir I.'
'Mlowe, Sixberth'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 N-{[5-(4-methylphenyl)-1,2-oxazol-3-yl]methyl}-1-phenyl-N-(prop-2-en-1-yl)methanesulfonamide
;
_journal_coeditor_code           JY2020
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022005035
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C21 H22 N2 O3 S'
_chemical_formula_moiety         'C21 H22 N2 O3 S'
_chemical_formula_sum            'C21 H22 N2 O3 S'
_chemical_formula_weight         382.46
_chemical_name_systematic
N-{[5-(4-Methylphenyl)-1,2-oxazol-3-yl]methyl}-1-phenyl-N-(prop-2-en-1-yl)methanesulfonamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.5260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.79790(10)
_cell_length_b                   10.2238(10)
_cell_length_c                   17.7316(2)
_cell_measurement_reflns_used    18074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.2
_cell_measurement_theta_min      5.0
_cell_volume                     1924.55(19)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2021)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2020)'
_computing_structure_refinement  'SHELXL2018 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21251
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.602
_diffrn_reflns_theta_min         5.015
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_T_max  0.779
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.576
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0451
_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)+(0.1004P)²+0.3109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                3542
_reflns_number_total             3572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2020sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               2244095
_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   0.687
_shelx_estimated_absorpt_t_max   0.798
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -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
S S1 0.20850(6) 0.59215(6) 0.37939(4) 0.0181(2) Uani d 1 . .
O O1 0.1034(2) 0.6795(2) 0.36066(12) 0.0253(5) Uani d 1 . .
O O2 0.1867(2) 0.4534(2) 0.37509(14) 0.0271(5) Uani d 1 . .
O O3 0.1016(2) 0.7878(2) 0.64904(11) 0.0248(5) Uani d 1 . .
N N1 0.2802(2) 0.6254(2) 0.46571(13) 0.0183(5) Uani d 1 . .
N N2 0.2125(3) 0.7725(3) 0.61968(15) 0.0259(6) Uani d 1 . .
C C1 0.3167(3) 0.6294(3) 0.31677(16) 0.0206(6) Uani d 1 . .
H H1A 0.390384 0.570343 0.328837 0.025 Uiso calc 1 . .
H H1B 0.275212 0.612336 0.263131 0.025 Uiso calc 1 . .
C C2 0.2760(3) 0.7586(3) 0.49593(15) 0.0180(5) Uani d 1 . .
H H2A 0.258277 0.820906 0.452560 0.022 Uiso calc 1 . .
H H2B 0.359354 0.780818 0.526667 0.022 Uiso calc 1 . .
C C3 0.1778(3) 0.7734(3) 0.54474(16) 0.0178(5) Uani d 1 . .
C C4 0.0450(3) 0.7881(3) 0.52263(15) 0.0179(5) Uani d 1 . .
H H4 -0.003053 0.791270 0.472112 0.022 Uiso calc 1 . .
C C5 0.0023(3) 0.7966(3) 0.58978(15) 0.0180(5) Uani d 1 . .
C C6 -0.1207(3) 0.8145(3) 0.61079(15) 0.0173(5) Uani d 1 . .
C C7 -0.1342(3) 0.8064(3) 0.68787(15) 0.0199(6) Uani d 1 . .
H H7 -0.063522 0.785401 0.726289 0.024 Uiso calc 1 . .
C C8 -0.2503(3) 0.8290(3) 0.70805(15) 0.0193(5) Uani d 1 . .
H H8 -0.258482 0.822084 0.760347 0.023 Uiso calc 1 . .
C C9 -0.3554(3) 0.8615(3) 0.65319(16) 0.0189(6) Uani d 1 . .
C C10 -0.3414(3) 0.8690(3) 0.57646(16) 0.0214(6) Uani d 1 . .
H H10 -0.412186 0.890631 0.538263 0.026 Uiso calc 1 . .
C C11 -0.2261(3) 0.8453(3) 0.55508(16) 0.0209(6) Uani d 1 . .
H H11 -0.218664 0.850017 0.502582 0.025 Uiso calc 1 . .
C C12 -0.4808(3) 0.8853(3) 0.67664(17) 0.0235(6) Uani d 1 . .
H H12A -0.470660 0.949937 0.718118 0.035 Uiso calc 1 . .
H H12B -0.512271 0.803142 0.694488 0.035 Uiso calc 1 . .
H H12C -0.540911 0.918217 0.632572 0.035 Uiso calc 1 . .
C C13 0.3384(3) 0.5231(3) 0.51956(18) 0.0233(6) Uani d 1 . .
H H13A 0.325804 0.436904 0.493807 0.028 Uiso calc 1 . .
H H13B 0.295250 0.521026 0.564246 0.028 Uiso calc 1 . .
C C14 0.4759(3) 0.5443(3) 0.5472(2) 0.0264(6) Uani d 1 . .
H H14 0.528386 0.555444 0.510125 0.032 Uiso calc 1 . .
C C15 0.5284(4) 0.5485(3) 0.6206(2) 0.0334(8) Uani d 1 . .
H H15A 0.477943 0.537711 0.658813 0.040 Uiso calc 1 . .
H H15B 0.616492 0.562376 0.635134 0.040 Uiso calc 1 . .
C C16 0.3618(3) 0.7690(3) 0.32347(15) 0.0189(6) Uani d 1 . .
C C17 0.2818(3) 0.8703(3) 0.29145(17) 0.0221(6) Uani d 1 . .
H H17 0.198709 0.850949 0.265671 0.026 Uiso calc 1 . .
C C18 0.3237(3) 0.9990(3) 0.29736(18) 0.0260(6) Uani d 1 . .
H H18 0.269020 1.067490 0.275926 0.031 Uiso calc 1 . .
C C19 0.4454(4) 1.0278(3) 0.33448(18) 0.0265(7) Uani d 1 . .
H H19 0.474088 1.115850 0.338020 0.032 Uiso calc 1 . .
C C20 0.5246(3) 0.9281(3) 0.36625(19) 0.0271(6) Uani d 1 . .
H H20 0.607762 0.947754 0.391695 0.033 Uiso calc 1 . .
C C21 0.4827(3) 0.7986(3) 0.36106(17) 0.0223(6) Uani d 1 . .
H H21 0.537283 0.730553 0.383366 0.027 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 O2 . . 119.14(15) ?
O1 S1 N1 . . 108.03(13) ?
O2 S1 N1 . . 107.60(13) ?
O1 S1 C1 . . 107.57(14) ?
O2 S1 C1 . . 107.18(14) ?
N1 S1 C1 . . 106.70(14) ?
C5 O3 N2 . . 109.1(2) ?
C2 N1 C13 . . 117.3(2) ?
C2 N1 S1 . . 119.87(19) ?
C13 N1 S1 . . 122.40(19) ?
C3 N2 O3 . . 105.7(2) ?
C16 C1 S1 . . 112.94(19) ?
C16 C1 H1A . . 109.0 ?
S1 C1 H1A . . 109.0 ?
C16 C1 H1B . . 109.0 ?
S1 C1 H1B . . 109.0 ?
H1A C1 H1B . . 107.8 ?
N1 C2 C3 . . 112.2(2) ?
N1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
N1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
N2 C3 C4 . . 111.5(3) ?
N2 C3 C2 . . 118.9(3) ?
C4 C3 C2 . . 129.6(3) ?
C5 C4 C3 . . 104.6(2) ?
C5 C4 H4 . . 127.7 ?
C3 C4 H4 . . 127.7 ?
C4 C5 O3 . . 109.2(3) ?
C4 C5 C6 . . 134.8(3) ?
O3 C5 C6 . . 116.0(2) ?
C11 C6 C7 . . 119.0(3) ?
C11 C6 C5 . . 120.7(2) ?
C7 C6 C5 . . 120.3(3) ?
C8 C7 C6 . . 120.1(3) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C9 . . 121.3(2) ?
C7 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C8 C9 C10 . . 118.3(3) ?
C8 C9 C12 . . 120.3(3) ?
C10 C9 C12 . . 121.4(3) ?
C11 C10 C9 . . 121.2(3) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C10 C11 C6 . . 120.1(3) ?
C10 C11 H11 . . 120.0 ?
C6 C11 H11 . . 120.0 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C13 C14 . . 112.9(3) ?
N1 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
N1 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C15 C14 C13 . . 123.4(3) ?
C15 C14 H14 . . 118.3 ?
C13 C14 H14 . . 118.3 ?
C14 C15 H15A . . 120.0 ?
C14 C15 H15B . . 120.0 ?
H15A C15 H15B . . 120.0 ?
C21 C16 C17 . . 119.3(3) ?
C21 C16 C1 . . 120.5(3) ?
C17 C16 C1 . . 120.2(3) ?
C18 C17 C16 . . 120.1(3) ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C19 C18 C17 . . 120.3(3) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C20 C19 C18 . . 119.8(3) ?
C20 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C19 C20 C21 . . 120.2(3) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C16 C21 C20 . . 120.3(3) ?
C16 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
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 O1 . 1.434(2) ?
S1 O2 . 1.438(2) ?
S1 N1 . 1.620(2) ?
S1 C1 . 1.794(3) ?
O3 C5 . 1.360(3) ?
O3 N2 . 1.399(3) ?
N1 C2 . 1.468(3) ?
N1 C13 . 1.477(4) ?
N2 C3 . 1.313(4) ?
C1 C16 . 1.506(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.494(4) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.424(4) ?
C4 C5 . 1.355(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.455(4) ?
C6 C11 . 1.400(4) ?
C6 C7 . 1.403(3) ?
C7 C8 . 1.385(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.393(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.398(4) ?
C9 C12 . 1.507(4) ?
C10 C11 . 1.388(4) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C14 . 1.492(5) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.322(5) ?
C14 H14 . 0.9500 ?
C15 H15A . 0.9500 ?
C15 H15B . 0.9500 ?
C16 C21 . 1.387(4) ?
C16 C17 . 1.401(4) ?
C17 C18 . 1.389(4) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.389(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.383(5) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.397(4) ?
C20 H20 . 0.9500 ?
C21 H21 . 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
C7 H7 O3 . 0.95 2.44 2.763(4) 100 no
C8 H8 O2 3_455 0.95 2.59 3.404(4) 143 yes
C13 H13A O2 . 0.99 2.36 2.867(4) 111 no
C17 H17 O3 4_464 0.95 2.57 3.314(4) 135 yes
C19 H19 O1 2_575 0.95 2.51 3.434(4) 165 yes
C21 H21 O2 2_565 0.95 2.50 3.369(4) 152 yes
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
O1 S1 N1 C2 . . . . -28.6(3) ?
O2 S1 N1 C2 . . . . -158.5(2) ?
C1 S1 N1 C2 . . . . 86.8(2) ?
O1 S1 N1 C13 . . . . 144.0(2) ?
O2 S1 N1 C13 . . . . 14.2(3) ?
C1 S1 N1 C13 . . . . -100.6(3) ?
C5 O3 N2 C3 . . . . 0.4(3) ?
O1 S1 C1 C16 . . . . 58.5(2) ?
O2 S1 C1 C16 . . . . -172.3(2) ?
N1 S1 C1 C16 . . . . -57.3(2) ?
C13 N1 C2 C3 . . . . -75.0(3) ?
S1 N1 C2 C3 . . . . 98.1(3) ?
O3 N2 C3 C4 . . . . -0.4(3) ?
O3 N2 C3 C2 . . . . -179.9(2) ?
N1 C2 C3 N2 . . . . 101.3(3) ?
N1 C2 C3 C4 . . . . -78.2(4) ?
N2 C3 C4 C5 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 179.7(3) ?
C3 C4 C5 O3 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 178.8(3) ?
N2 O3 C5 C4 . . . . -0.2(3) ?
N2 O3 C5 C6 . . . . -179.3(2) ?
C4 C5 C6 C11 . . . . -8.8(5) ?
O3 C5 C6 C11 . . . . 169.9(2) ?
C4 C5 C6 C7 . . . . 173.8(3) ?
O3 C5 C6 C7 . . . . -7.5(4) ?
C11 C6 C7 C8 . . . . -0.2(4) ?
C5 C6 C7 C8 . . . . 177.3(3) ?
C6 C7 C8 C9 . . . . -0.8(4) ?
C7 C8 C9 C10 . . . . 1.0(4) ?
C7 C8 C9 C12 . . . . 179.9(3) ?
C8 C9 C10 C11 . . . . -0.3(4) ?
C12 C9 C10 C11 . . . . -179.1(3) ?
C9 C10 C11 C6 . . . . -0.6(4) ?
C7 C6 C11 C10 . . . . 0.8(4) ?
C5 C6 C11 C10 . . . . -176.6(3) ?
C2 N1 C13 C14 . . . . -65.6(3) ?
S1 N1 C13 C14 . . . . 121.6(3) ?
N1 C13 C14 C15 . . . . 126.2(3) ?
S1 C1 C16 C21 . . . . 105.6(3) ?
S1 C1 C16 C17 . . . . -74.6(3) ?
C21 C16 C17 C18 . . . . 0.1(4) ?
C1 C16 C17 C18 . . . . -179.7(3) ?
C16 C17 C18 C19 . . . . 0.5(5) ?
C17 C18 C19 C20 . . . . -0.6(5) ?
C18 C19 C20 C21 . . . . 0.1(5) ?
C17 C16 C21 C20 . . . . -0.6(4) ?
C1 C16 C21 C20 . . . . 179.2(3) ?
C19 C20 C21 C16 . . . . 0.5(5) ?

_cod_database_fobs_code 2244095
