#------------------------------------------------------------------------------
#$Date: 2022-06-11 04:49:39 +0300 (Sat, 11 Jun 2022) $
#$Revision: 275968 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244110.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_2244110
loop_
_publ_author_name
'Khalilov, Ali N.'
'Khrustalev, Victor N.'
'Fortalnova, Elena A.'
'Akkurt, Mehmet'
'Yıldırım, Sema Öztürk'
'Bhattarai, Ajaya'
'Mamedov, İbrahim G.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol
;
_journal_coeditor_code           TX2051
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022005928
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C20 H24 Br N O2'
_chemical_formula_moiety         'C20 H24 Br N O2'
_chemical_formula_sum            'C20 H24 Br N O2'
_chemical_formula_weight         390.30
_chemical_name_systematic
;
4-Bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol
;
_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   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.1425(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.1019(3)
_cell_length_b                   9.01359(11)
_cell_length_c                   10.03985(11)
_cell_measurement_reflns_used    13703
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.56
_cell_measurement_theta_min      2.14
_cell_volume                     1898.65(4)
_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 0.994
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21431
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.607
_diffrn_reflns_theta_min         2.106
_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    3.033
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.597
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.055P)²+1.11P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                3783
_reflns_number_total             4096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2051sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1898.66(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244110
_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   0.444
_shelx_estimated_absorpt_t_max   0.915
_shelxl_version_number           .2013
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
Br Br1 0.54220(2) 0.31515(2) 0.43375(2) 0.02813(9) Uani d 1 . .
O O1 0.27633(7) 0.25150(17) 0.58702(14) 0.0298(3) Uani d 1 . .
C C2 0.32957(9) 0.1726(2) 0.65118(19) 0.0232(4) Uani d 1 . .
H H2 0.3517 0.2334 0.7256 0.028 Uiso calc 1 . .
N N3 0.30119(8) 0.03941(18) 0.70533(15) 0.0240(3) Uani d 1 . .
C C4 0.24396(10) 0.0998(2) 0.7578(2) 0.0286(4) Uani d 1 . .
H H4A 0.2548 0.1518 0.8441 0.034 Uiso calc 1 . .
H H4B 0.2124 0.0210 0.7696 0.034 Uiso calc 1 . .
C C5 0.21970(10) 0.2075(2) 0.6467(2) 0.0275(4) Uani d 1 . .
H H5 0.1901 0.1541 0.5785 0.033 Uiso calc 1 . .
C C6 0.37483(9) 0.1367(2) 0.54907(18) 0.0226(4) Uani d 1 . .
C C7 0.42805(9) 0.2251(2) 0.53991(18) 0.0235(4) Uani d 1 . .
H H7 0.4364 0.3066 0.5991 0.028 Uiso calc 1 . .
C C8 0.46904(9) 0.1942(2) 0.44404(19) 0.0229(4) Uani d 1 . .
C C9 0.45780(9) 0.0753(2) 0.35676(18) 0.0238(4) Uani d 1 . .
H H9 0.4865 0.0541 0.2925 0.029 Uiso calc 1 . .
C C10 0.40439(10) -0.0118(2) 0.36452(18) 0.0255(4) Uani d 1 . .
H H10 0.3961 -0.0925 0.3043 0.031 Uiso calc 1 . .
C C11 0.36252(9) 0.0175(2) 0.45995(18) 0.0237(4) Uani d 1 . .
O O11 0.31123(7) -0.07205(17) 0.46493(15) 0.0287(3) Uani d 1 . .
H H11 0.2980(17) -0.053(4) 0.536(4) 0.050(9) Uiso d 1 . .
C C12 0.34457(10) -0.0365(2) 0.8069(2) 0.0295(4) Uani d 1 . .
H H12A 0.3823 -0.0707 0.7665 0.044 Uiso calc 1 . .
H H12B 0.3228 -0.1218 0.8418 0.044 Uiso calc 1 . .
H H12C 0.3577 0.0323 0.8803 0.044 Uiso calc 1 . .
C C13 0.18595(10) 0.3429(2) 0.6965(2) 0.0293(4) Uani d 1 . .
H H13A 0.1502 0.3093 0.7453 0.035 Uiso calc 1 . .
H H13B 0.2162 0.3982 0.7606 0.035 Uiso calc 1 . .
C C14 0.16029(10) 0.4466(2) 0.5851(2) 0.0288(4) Uani d 1 . .
C C15 0.19383(11) 0.5761(2) 0.5574(2) 0.0301(4) Uani d 1 . .
C C16 0.16792(12) 0.6723(3) 0.4563(2) 0.0361(5) Uani d 1 . .
H H16 0.1904 0.7603 0.4389 0.043 Uiso calc 1 . .
C C17 0.11055(12) 0.6426(3) 0.3812(3) 0.0430(6) Uani d 1 . .
C C18 0.07858(11) 0.5135(4) 0.4079(3) 0.0452(6) Uani d 1 . .
H H18 0.0393 0.4915 0.3564 0.054 Uiso calc 1 . .
C C19 0.10236(10) 0.4145(3) 0.5084(2) 0.0365(5) Uani d 1 . .
C C20 0.25709(13) 0.6141(3) 0.6335(2) 0.0393(5) Uani d 1 . .
H H20A 0.2512 0.6344 0.7273 0.059 Uiso calc 1 . .
H H20B 0.2748 0.7021 0.5938 0.059 Uiso calc 1 . .
H H20C 0.2865 0.5304 0.6291 0.059 Uiso calc 1 . .
C C21 0.08362(15) 0.7492(5) 0.2732(3) 0.0650(10) Uani d 1 . .
H H21A 0.0776 0.8468 0.3131 0.097 Uiso calc 1 . .
H H21B 0.0425 0.7119 0.2318 0.097 Uiso calc 1 . .
H H21C 0.1133 0.7581 0.2050 0.097 Uiso calc 1 . .
C C22 0.06445(12) 0.2765(4) 0.5315(3) 0.0523(7) Uani d 1 . .
H H22A 0.0859 0.1897 0.4985 0.079 Uiso calc 1 . .
H H22B 0.0217 0.2853 0.4835 0.079 Uiso calc 1 . .
H H22C 0.0611 0.2651 0.6276 0.079 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'
Br Br -0.6763 1.2805 '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'
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 O1 C5 . . 108.79(14) ?
O1 C2 N3 . . 104.01(15) ?
O1 C2 C6 . . 109.02(15) ?
N3 C2 C6 . . 112.83(16) ?
O1 C2 H2 . . 110.3 ?
N3 C2 H2 . . 110.3 ?
C6 C2 H2 . . 110.3 ?
C12 N3 C2 . . 112.92(16) ?
C12 N3 C4 . . 113.51(15) ?
C2 N3 C4 . . 102.26(15) ?
N3 C4 C5 . . 101.41(15) ?
N3 C4 H4A . . 111.5 ?
C5 C4 H4A . . 111.5 ?
N3 C4 H4B . . 111.5 ?
C5 C4 H4B . . 111.5 ?
H4A C4 H4B . . 109.3 ?
O1 C5 C13 . . 110.61(17) ?
O1 C5 C4 . . 104.45(16) ?
C13 C5 C4 . . 113.71(17) ?
O1 C5 H5 . . 109.3 ?
C13 C5 H5 . . 109.3 ?
C4 C5 H5 . . 109.3 ?
C7 C6 C11 . . 119.50(17) ?
C7 C6 C2 . . 119.82(17) ?
C11 C6 C2 . . 120.64(17) ?
C6 C7 C8 . . 119.94(18) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 121.00(18) ?
C9 C8 Br1 . . 119.54(14) ?
C7 C8 Br1 . . 119.46(15) ?
C10 C9 C8 . . 119.20(17) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
C9 C10 C11 . . 120.70(18) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
O11 C11 C10 . . 118.61(18) ?
O11 C11 C6 . . 121.74(17) ?
C10 C11 C6 . . 119.65(18) ?
C11 O11 H11 . . 105(2) ?
N3 C12 H12A . . 109.5 ?
N3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C5 . . 113.25(17) ?
C14 C13 H13A . . 108.9 ?
C5 C13 H13A . . 108.9 ?
C14 C13 H13B . . 108.9 ?
C5 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.7 ?
C19 C14 C15 . . 119.3(2) ?
C19 C14 C13 . . 120.0(2) ?
C15 C14 C13 . . 120.7(2) ?
C16 C15 C14 . . 119.4(2) ?
C16 C15 C20 . . 118.9(2) ?
C14 C15 C20 . . 121.7(2) ?
C17 C16 C15 . . 121.8(2) ?
C17 C16 H16 . . 119.1 ?
C15 C16 H16 . . 119.1 ?
C16 C17 C18 . . 118.2(2) ?
C16 C17 C21 . . 120.5(3) ?
C18 C17 C21 . . 121.3(3) ?
C17 C18 C19 . . 122.1(2) ?
C17 C18 H18 . . 119.0 ?
C19 C18 H18 . . 119.0 ?
C18 C19 C14 . . 119.2(2) ?
C18 C19 C22 . . 118.8(2) ?
C14 C19 C22 . . 122.0(2) ?
C15 C20 H20A . . 109.5 ?
C15 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C15 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C17 C21 H21A . . 109.5 ?
C17 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C17 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C19 C22 H22A . . 109.5 ?
C19 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C19 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 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
Br1 C8 . 1.9019(19) ?
O1 C2 . 1.424(2) ?
O1 C5 . 1.448(2) ?
C2 N3 . 1.472(2) ?
C2 C6 . 1.509(3) ?
C2 H2 . 1.0000 ?
N3 C12 . 1.465(2) ?
N3 C4 . 1.472(3) ?
C4 C5 . 1.525(3) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C13 . 1.524(3) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.388(3) ?
C6 C11 . 1.404(3) ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.388(3) ?
C9 C10 . 1.383(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.396(3) ?
C10 H10 . 0.9500 ?
C11 O11 . 1.356(2) ?
O11 H11 . 0.81(4) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C14 . 1.513(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C19 . 1.404(3) ?
C14 C15 . 1.407(3) ?
C15 C16 . 1.401(3) ?
C15 C20 . 1.505(3) ?
C16 C17 . 1.382(4) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.385(4) ?
C17 C21 . 1.513(4) ?
C18 C19 . 1.399(4) ?
C18 H18 . 0.9500 ?
C19 C22 . 1.510(4) ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 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
_geom_hbond_publ_flag
O11 H11 N3 . 0.81(4) 1.89(4) 2.644(2) 155(3) yes
C4 H4A O1 4_566 0.99 2.58 3.564(2) 171 yes
C20 H20B O11 1_565 0.98 2.57 3.548(3) 173 yes
C20 H20C O1 . 0.98 2.55 3.332(3) 136 yes
C2 H2 Cg2 4_566 1.00 2.91 3.908(2) 176 yes
C4 H4B Cg3 4_566 0.99 2.88 3.622(2) 132 yes
C21 H21C Cg3 4_575 0.98 2.93 3.723(4) 138 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
C5 O1 C2 N3 . . . . 23.8(2) ?
C5 O1 C2 C6 . . . . 144.39(16) ?
O1 C2 N3 C12 . . . . -163.70(15) ?
C6 C2 N3 C12 . . . . 78.3(2) ?
O1 C2 N3 C4 . . . . -41.36(18) ?
C6 C2 N3 C4 . . . . -159.35(16) ?
C12 N3 C4 C5 . . . . 163.78(17) ?
C2 N3 C4 C5 . . . . 41.84(18) ?
C2 O1 C5 C13 . . . . 125.28(18) ?
C2 O1 C5 C4 . . . . 2.6(2) ?
N3 C4 C5 O1 . . . . -27.6(2) ?
N3 C4 C5 C13 . . . . -148.32(17) ?
O1 C2 C6 C7 . . . . 98.9(2) ?
N3 C2 C6 C7 . . . . -146.13(17) ?
O1 C2 C6 C11 . . . . -79.0(2) ?
N3 C2 C6 C11 . . . . 36.0(2) ?
C11 C6 C7 C8 . . . . -0.7(3) ?
C2 C6 C7 C8 . . . . -178.59(17) ?
C6 C7 C8 C9 . . . . -0.2(3) ?
C6 C7 C8 Br1 . . . . -179.44(14) ?
C7 C8 C9 C10 . . . . 1.0(3) ?
Br1 C8 C9 C10 . . . . -179.76(14) ?
C8 C9 C10 C11 . . . . -0.9(3) ?
C9 C10 C11 O11 . . . . -179.15(17) ?
C9 C10 C11 C6 . . . . -0.1(3) ?
C7 C6 C11 O11 . . . . 179.93(17) ?
C2 C6 C11 O11 . . . . -2.2(3) ?
C7 C6 C11 C10 . . . . 0.9(3) ?
C2 C6 C11 C10 . . . . 178.71(17) ?
O1 C5 C13 C14 . . . . 64.6(2) ?
C4 C5 C13 C14 . . . . -178.21(18) ?
C5 C13 C14 C19 . . . . 80.4(2) ?
C5 C13 C14 C15 . . . . -99.8(2) ?
C19 C14 C15 C16 . . . . 1.7(3) ?
C13 C14 C15 C16 . . . . -178.05(18) ?
C19 C14 C15 C20 . . . . -178.2(2) ?
C13 C14 C15 C20 . . . . 2.1(3) ?
C14 C15 C16 C17 . . . . -1.0(3) ?
C20 C15 C16 C17 . . . . 178.9(2) ?
C15 C16 C17 C18 . . . . -0.1(4) ?
C15 C16 C17 C21 . . . . 179.6(2) ?
C16 C17 C18 C19 . . . . 0.5(4) ?
C21 C17 C18 C19 . . . . -179.2(3) ?
C17 C18 C19 C14 . . . . 0.2(4) ?
C17 C18 C19 C22 . . . . 179.8(3) ?
C15 C14 C19 C18 . . . . -1.3(3) ?
C13 C14 C19 C18 . . . . 178.4(2) ?
C15 C14 C19 C22 . . . . 179.1(2) ?
C13 C14 C19 C22 . . . . -1.1(3) ?

_cod_database_fobs_code 2244110
