#------------------------------------------------------------------------------
#$Date: 2021-03-06 08:21:11 +0200 (Sat, 06 Mar 2021) $
#$Revision: 262793 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243772.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_2243772
loop_
_publ_author_name
'Aydin, Abdullah'
'Akkurt, Mehmet'
'Turanli, Sumeyye'
'Lengerli, Deniz'
'Banoglu, Erden'
'Ozcelik, Nefise Dilek'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-(4-chlorophenyl)-5-methyl-3-{4-[(2-methylphenyl)methoxy]phenyl}-1,2-oxazole
;
_journal_coeditor_code           YK2147
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              346
_journal_page_last               350
_journal_paper_doi               10.1107/S2056989021002383
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C24 H20 Cl N O2'
_chemical_formula_moiety         'C24 H20 Cl N O2'
_chemical_formula_sum            'C24 H20 Cl N O2'
_chemical_formula_weight         389.86
_chemical_name_systematic
;
4-(4-Chlorophenyl)-5-methyl-3-{4-[(2-methylphenyl)methoxy]phenyl}-1,2-oxazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 101.477(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5733(10)
_cell_length_b                   22.848(2)
_cell_length_c                   8.7151(9)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.91
_cell_volume                     2063.3(3)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020) and WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/4 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART BREEZE CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            45630
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.912
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.328
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0993
_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)+(0.0303P)²+3.1816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1866
_reflns_number_gt                3030
_reflns_number_total             3840
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2147sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2063.3(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243772
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.9916(5) 0.3972(2) 0.0798(6) 0.0786(15) Uani d 1 . .
H H1A 1.073792 0.414990 0.079720 0.118 Uiso calc 1 . .
H H1B 0.949677 0.388351 -0.025762 0.118 Uiso calc 1 . .
H H1C 1.003929 0.361730 0.140061 0.118 Uiso calc 1 . .
C C2 0.9100(4) 0.43821(19) 0.1503(5) 0.0575(11) Uani d 1 . .
C C3 0.8681(4) 0.43905(16) 0.2861(4) 0.0445(9) Uani d 1 . .
C C4 0.7911(4) 0.49060(16) 0.2788(4) 0.0477(9) Uani d 1 . .
C C5 0.8951(3) 0.39390(15) 0.4106(4) 0.0399(8) Uani d 1 . .
C C6 1.0198(4) 0.38314(18) 0.4902(5) 0.0559(11) Uani d 1 . .
H H6 1.087573 0.404533 0.464626 0.067 Uiso calc 1 . .
C C7 1.0458(4) 0.34153(19) 0.6061(5) 0.0601(11) Uani d 1 . .
H H7 1.129976 0.334858 0.658977 0.072 Uiso calc 1 . .
C C8 0.9461(4) 0.31025(16) 0.6423(4) 0.0505(10) Uani d 1 . .
C C9 0.8221(4) 0.31897(17) 0.5654(4) 0.0513(10) Uani d 1 . .
H H9 0.755403 0.296826 0.590784 0.062 Uiso calc 1 . .
C C10 0.7965(4) 0.36096(17) 0.4494(4) 0.0474(9) Uani d 1 . .
H H10 0.712000 0.367117 0.396865 0.057 Uiso calc 1 . .
C C11 0.7223(4) 0.51653(15) 0.3940(4) 0.0434(9) Uani d 1 . .
C C12 0.7465(4) 0.50001(17) 0.5498(5) 0.0534(10) Uani d 1 . .
H H12 0.804645 0.469849 0.582691 0.064 Uiso calc 1 . .
C C13 0.6866(4) 0.52715(17) 0.6581(5) 0.0560(11) Uani d 1 . .
H H13 0.703823 0.515063 0.762061 0.067 Uiso calc 1 . .
C C14 0.6014(4) 0.57204(18) 0.6108(4) 0.0511(10) Uani d 1 . .
C C15 0.5757(4) 0.5890(2) 0.4563(5) 0.0638(12) Uani d 1 . .
H H15 0.517749 0.619299 0.423717 0.077 Uiso calc 1 . .
C C16 0.6351(4) 0.5615(2) 0.3503(5) 0.0604(11) Uani d 1 . .
H H16 0.616425 0.573436 0.246158 0.072 Uiso calc 1 . .
C C17 0.5646(5) 0.5876(2) 0.8714(5) 0.0726(14) Uani d 1 . .
H H17A 0.656655 0.583009 0.909755 0.087 Uiso calc 1 . .
H H17B 0.522468 0.550907 0.885738 0.087 Uiso calc 1 . .
C C18 0.5135(4) 0.6354(2) 0.9591(4) 0.0599(12) Uani d 1 . .
C C19 0.4002(5) 0.6258(3) 1.0119(6) 0.0900(17) Uani d 1 . .
H H19 0.356626 0.590511 0.988715 0.108 Uiso calc 1 . .
C C20 0.3513(7) 0.6669(5) 1.0973(8) 0.130(3) Uani d 1 . .
H H20 0.275977 0.659313 1.133673 0.156 Uiso calc 1 . .
C C21 0.4116(11) 0.7181(4) 1.1287(9) 0.136(4) Uani d 1 . .
H H21 0.377369 0.746428 1.185453 0.163 Uiso calc 1 . .
C C22 0.5229(9) 0.7290(3) 1.0780(8) 0.117(3) Uani d 1 . .
H H22 0.563766 0.764957 1.100443 0.140 Uiso calc 1 . .
C C23 0.5775(6) 0.6873(3) 0.9926(6) 0.0797(15) Uani d 1 . .
C C24 0.7025(7) 0.6991(3) 0.9434(8) 0.134(3) Uani d 1 . .
H H24A 0.769778 0.676652 1.007418 0.200 Uiso calc 1 . .
H H24B 0.722625 0.739980 0.955410 0.200 Uiso calc 1 . .
H H24C 0.695494 0.688090 0.835677 0.200 Uiso calc 1 . .
Cl Cl1 0.97763(16) 0.25691(6) 0.78820(15) 0.0889(5) Uani d 1 . .
N N1 0.7874(4) 0.51849(16) 0.1458(4) 0.0666(10) Uani d 1 . .
O O1 0.8631(3) 0.48497(14) 0.0621(3) 0.0709(9) Uani d 1 . .
O O2 0.5395(3) 0.60330(14) 0.7082(3) 0.0668(9) 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 O1 . . 110.0(4) ?
C3 C2 C1 . . 133.8(4) ?
O1 C2 C1 . . 116.2(4) ?
C2 C3 C4 . . 104.9(3) ?
C2 C3 C5 . . 125.8(4) ?
C4 C3 C5 . . 129.2(3) ?
N1 C4 C3 . . 110.8(3) ?
N1 C4 C11 . . 118.2(3) ?
C3 C4 C11 . . 131.0(3) ?
C10 C5 C6 . . 118.1(3) ?
C10 C5 C3 . . 120.9(3) ?
C6 C5 C3 . . 121.0(3) ?
C7 C6 C5 . . 121.4(4) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C8 C7 C6 . . 118.9(4) ?
C8 C7 H7 . . 120.6 ?
C6 C7 H7 . . 120.6 ?
C7 C8 C9 . . 121.5(4) ?
C7 C8 Cl1 . . 119.4(3) ?
C9 C8 Cl1 . . 119.1(3) ?
C8 C9 C10 . . 119.4(3) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
C9 C10 C5 . . 120.7(4) ?
C9 C10 H10 . . 119.7 ?
C5 C10 H10 . . 119.7 ?
C16 C11 C12 . . 117.1(4) ?
C16 C11 C4 . . 120.2(3) ?
C12 C11 C4 . . 122.6(3) ?
C11 C12 C13 . . 121.8(4) ?
C11 C12 H12 . . 119.1 ?
C13 C12 H12 . . 119.1 ?
C14 C13 C12 . . 119.5(4) ?
C14 C13 H13 . . 120.3 ?
C12 C13 H13 . . 120.3 ?
O2 C14 C13 . . 124.7(3) ?
O2 C14 C15 . . 115.7(3) ?
C13 C14 C15 . . 119.6(4) ?
C16 C15 C14 . . 120.2(4) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C11 . . 121.7(4) ?
C15 C16 H16 . . 119.1 ?
C11 C16 H16 . . 119.1 ?
O2 C17 C18 . . 108.0(3) ?
O2 C17 H17A . . 110.1 ?
C18 C17 H17A . . 110.1 ?
O2 C17 H17B . . 110.1 ?
C18 C17 H17B . . 110.1 ?
H17A C17 H17B . . 108.4 ?
C23 C18 C19 . . 119.4(5) ?
C23 C18 C17 . . 121.9(5) ?
C19 C18 C17 . . 118.6(5) ?
C20 C19 C18 . . 121.3(7) ?
C20 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C21 C20 C19 . . 119.9(8) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C20 C21 C22 . . 120.2(8) ?
C20 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
C21 C22 C23 . . 121.5(8) ?
C21 C22 H22 . . 119.3 ?
C23 C22 H22 . . 119.3 ?
C18 C23 C22 . . 117.7(6) ?
C18 C23 C24 . . 121.5(6) ?
C22 C23 C24 . . 120.8(7) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C4 N1 O1 . . 105.8(3) ?
C2 O1 N1 . . 108.5(3) ?
C14 O2 C17 . . 117.7(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
C1 C2 . 1.487(6) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.344(5) ?
C2 O1 . 1.351(5) ?
C3 C4 . 1.426(5) ?
C3 C5 . 1.483(5) ?
C4 N1 . 1.317(5) ?
C4 C11 . 1.476(5) ?
C5 C10 . 1.381(5) ?
C5 C6 . 1.384(5) ?
C6 C7 . 1.375(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.361(6) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.363(6) ?
C8 Cl1 . 1.745(4) ?
C9 C10 . 1.381(5) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C16 . 1.383(5) ?
C11 C12 . 1.383(5) ?
C12 C13 . 1.384(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.373(5) ?
C13 H13 . 0.9300 ?
C14 O2 . 1.371(5) ?
C14 C15 . 1.376(5) ?
C15 C16 . 1.369(6) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 O2 . 1.439(5) ?
C17 C18 . 1.494(6) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C23 . 1.368(7) ?
C18 C19 . 1.383(7) ?
C19 C20 . 1.364(9) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.334(12) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.361(11) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.402(9) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.493(8) ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
N1 O1 . 1.411(4) ?
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
C17 H17A N1 1_556 0.97 2.68 3.395(6) 130.8 yes
C6 H6 Cg3 3_766 0.93 2.86 3.747(5) 159 yes
C19 H19 Cg1 3_666 0.93 2.77 3.614(6) 151 yes
C8 Cl1 Cg2 4_555 1.745(4) 3.366(2) 5.034(4) 158.94(16) 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 C2 C3 C4 . . . . -0.5(5) ?
C1 C2 C3 C4 . . . . -179.0(5) ?
O1 C2 C3 C5 . . . . 177.6(3) ?
C1 C2 C3 C5 . . . . -0.9(8) ?
C2 C3 C4 N1 . . . . 0.2(5) ?
C5 C3 C4 N1 . . . . -177.8(4) ?
C2 C3 C4 C11 . . . . -177.8(4) ?
C5 C3 C4 C11 . . . . 4.2(7) ?
C2 C3 C5 C10 . . . . -115.9(5) ?
C4 C3 C5 C10 . . . . 61.7(5) ?
C2 C3 C5 C6 . . . . 63.4(6) ?
C4 C3 C5 C6 . . . . -119.0(5) ?
C10 C5 C6 C7 . . . . -0.9(6) ?
C3 C5 C6 C7 . . . . 179.8(4) ?
C5 C6 C7 C8 . . . . 0.3(7) ?
C6 C7 C8 C9 . . . . 0.6(6) ?
C6 C7 C8 Cl1 . . . . 179.5(3) ?
C7 C8 C9 C10 . . . . -0.8(6) ?
Cl1 C8 C9 C10 . . . . -179.8(3) ?
C8 C9 C10 C5 . . . . 0.2(6) ?
C6 C5 C10 C9 . . . . 0.6(6) ?
C3 C5 C10 C9 . . . . 180.0(3) ?
N1 C4 C11 C16 . . . . 13.4(6) ?
C3 C4 C11 C16 . . . . -168.7(4) ?
N1 C4 C11 C12 . . . . -162.7(4) ?
C3 C4 C11 C12 . . . . 15.1(6) ?
C16 C11 C12 C13 . . . . 0.0(6) ?
C4 C11 C12 C13 . . . . 176.2(4) ?
C11 C12 C13 C14 . . . . -0.5(7) ?
C12 C13 C14 O2 . . . . -177.9(4) ?
C12 C13 C14 C15 . . . . 0.7(7) ?
O2 C14 C15 C16 . . . . 178.4(4) ?
C13 C14 C15 C16 . . . . -0.3(7) ?
C14 C15 C16 C11 . . . . -0.3(7) ?
C12 C11 C16 C15 . . . . 0.5(6) ?
C4 C11 C16 C15 . . . . -175.9(4) ?
O2 C17 C18 C23 . . . . -77.0(5) ?
O2 C17 C18 C19 . . . . 105.2(5) ?
C23 C18 C19 C20 . . . . -0.3(8) ?
C17 C18 C19 C20 . . . . 177.7(5) ?
C18 C19 C20 C21 . . . . 1.3(10) ?
C19 C20 C21 C22 . . . . -1.1(12) ?
C20 C21 C22 C23 . . . . -0.2(11) ?
C19 C18 C23 C22 . . . . -1.0(7) ?
C17 C18 C23 C22 . . . . -178.8(4) ?
C19 C18 C23 C24 . . . . 177.7(5) ?
C17 C18 C23 C24 . . . . -0.1(7) ?
C21 C22 C23 C18 . . . . 1.2(9) ?
C21 C22 C23 C24 . . . . -177.5(6) ?
C3 C4 N1 O1 . . . . 0.2(5) ?
C11 C4 N1 O1 . . . . 178.4(3) ?
C3 C2 O1 N1 . . . . 0.6(5) ?
C1 C2 O1 N1 . . . . 179.4(4) ?
C4 N1 O1 C2 . . . . -0.5(5) ?
C13 C14 O2 C17 . . . . -0.5(6) ?
C15 C14 O2 C17 . . . . -179.2(4) ?
C18 C17 O2 C14 . . . . 166.7(4) ?

_cod_database_fobs_code 2243772
