#------------------------------------------------------------------------------
#$Date: 2022-02-22 04:56:09 +0200 (Tue, 22 Feb 2022) $
#$Revision: 273079 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/25/2022568.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_2022568
loop_
_publ_author_name
'Muresan-Pop, Marieta'
'Macavei, Sergiu'
'Turza, Alexandru'
'Borodi, Gheorghe'
_publ_section_title
;
 New solvates and a salt of the anti-HIV compound etravirine
;
_journal_coeditor_code           VP3022
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              698
_journal_page_last               706
_journal_paper_doi               10.1107/S2053229621010482
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C20 H15 Br N6 O, C2 H6 O S'
_chemical_formula_moiety         'C20 H15 Br N6 O, C2 H6 O S'
_chemical_formula_sum            'C22 H21 Br N6 O2 S'
_chemical_formula_weight         513.42
_chemical_name_common            'Etravirine dimethyl sulfoxide monosolvate'
_chemical_name_systematic
'4-({6-Amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile dimethyl sulfoxide monosolvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                96.181(6)
_cell_angle_beta                 102.323(6)
_cell_angle_gamma                95.632(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6953(5)
_cell_length_b                   9.3336(8)
_cell_length_c                   15.1494(11)
_cell_measurement_reflns_used    4741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8485
_cell_measurement_theta_min      3.0098
_cell_volume                     1184.87(15)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.4335
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova Dual Source diffractometer with an Eos detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7279
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.986
_diffrn_reflns_theta_min         3.012
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    3.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       needle
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.661
_refine_diff_density_min         -1.684
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1460P)²+0.1471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1919
_refine_ls_wR_factor_ref         0.2101
_reflns_number_gt                3732
_reflns_number_total             4449
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3022sup1.cif
_cod_data_source_block           ETR-DMSO2
_cod_database_code               2022568
_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, -z'
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 0.15142(4) 0.39515(5) 0.07791(3) 0.0631(2) Uani d 1 . .
S S1 0.71828(12) -0.04858(11) 0.43617(9) 0.0661(3) Uani d 1 . .
O O1 0.4480(3) 0.2464(3) 0.09151(18) 0.0495(6) Uani d 1 . .
N N5 0.6174(3) 0.3974(3) 0.2109(2) 0.0411(6) Uani d 1 . .
N N3 0.5264(4) 0.6065(3) 0.2789(2) 0.0445(6) Uani d 1 . .
C C11 0.4745(4) 0.3661(3) 0.1554(2) 0.0405(7) Uani d 1 . .
C C10 0.3519(4) 0.4473(3) 0.1570(2) 0.0433(7) Uani d 1 . .
C C8 0.6366(4) 0.5184(3) 0.2701(2) 0.0397(7) Uani d 1 . .
C C12 0.5562(4) 0.1440(3) 0.1054(2) 0.0417(7) Uani d 1 . .
N N2 0.7791(3) 0.5617(3) 0.3291(2) 0.0469(7) Uani d 1 . .
H H2 0.782232 0.639829 0.365459 0.056 Uiso calc 1 . .
C C6 0.9480(4) 0.3774(4) 0.2881(3) 0.0508(8) Uani d 1 . .
H H6 0.867907 0.329941 0.240004 0.061 Uiso calc 1 . .
C C9 0.3826(4) 0.5704(3) 0.2233(3) 0.0447(7) Uani d 1 . .
N N4 0.2721(4) 0.6596(3) 0.2330(3) 0.0565(8) Uani d 1 . .
H H4A 0.179273 0.610360 0.219284 0.068 Uiso d 1 . .
H H4B 0.291873 0.700055 0.288675 0.068 Uiso d 1 . .
C C5 0.9215(4) 0.5005(3) 0.3406(2) 0.0415(7) Uani d 1 . .
C C14 0.6851(4) 0.1546(4) 0.0652(3) 0.0507(8) Uani d 1 . .
O O2 0.8308(4) -0.1614(3) 0.4448(3) 0.0795(10) Uani d 1 . .
C C2 1.2145(4) 0.3938(4) 0.3787(3) 0.0474(8) Uani d 1 . .
C C19 0.5195(4) 0.0338(4) 0.1541(3) 0.0487(8) Uani d 1 . .
N N1 1.4800(5) 0.2875(5) 0.4136(3) 0.0765(12) Uani d 1 . .
C C18 0.6217(6) -0.0717(4) 0.1645(3) 0.0592(10) Uani d 1 . .
H H18 0.600663 -0.148393 0.196396 0.071 Uiso calc 1 . .
C C1 1.3639(5) 0.3362(4) 0.3989(3) 0.0556(9) Uani d 1 . .
C C7 1.0937(5) 0.3258(4) 0.3076(3) 0.0546(9) Uani d 1 . .
H H7 1.110565 0.243678 0.272127 0.066 Uiso calc 1 . .
C C16 0.7547(5) -0.0636(5) 0.1278(3) 0.0615(11) Uani d 1 . .
C C3 1.1896(5) 0.5181(4) 0.4305(3) 0.0553(9) Uani d 1 . .
H H3 1.270341 0.565683 0.478185 0.066 Uiso calc 1 . .
C C13 0.7171(6) 0.2766(6) 0.0127(3) 0.0724(12) Uani d 1 . .
H H13A 0.620990 0.289252 -0.029014 0.109 Uiso calc 1 . .
H H13B 0.795840 0.254414 -0.020776 0.109 Uiso calc 1 . .
H H13C 0.755032 0.364396 0.054061 0.109 Uiso calc 1 . .
C C4 1.0453(4) 0.5708(4) 0.4110(3) 0.0525(9) Uani d 1 . .
H H4 1.030124 0.654759 0.445415 0.063 Uiso calc 1 . .
C C22 0.7398(7) 0.0439(5) 0.5481(4) 0.0793(14) Uani d 1 . .
H H22A 0.700005 -0.021129 0.585320 0.119 Uiso calc 1 . .
H H22B 0.681042 0.125759 0.545185 0.119 Uiso calc 1 . .
H H22C 0.849919 0.076755 0.574066 0.119 Uiso calc 1 . .
C C15 0.7854(5) 0.0477(5) 0.0777(3) 0.0603(10) Uani d 1 . .
H H15 0.873735 0.050676 0.052169 0.072 Uiso calc 1 . .
C C20 0.3756(6) 0.0299(5) 0.1952(4) 0.0746(13) Uani d 1 . .
H H20A 0.393232 0.105933 0.245565 0.112 Uiso calc 1 . .
H H20B 0.357626 -0.062407 0.216216 0.112 Uiso calc 1 . .
H H20C 0.284447 0.043625 0.149931 0.112 Uiso calc 1 . .
C C21 0.8112(7) 0.0968(6) 0.3918(4) 0.0763(13) Uani d 1 . .
H H21A 0.914895 0.128674 0.429735 0.114 Uiso calc 1 . .
H H21B 0.748422 0.175961 0.390546 0.114 Uiso calc 1 . .
H H21C 0.820433 0.064351 0.331007 0.114 Uiso calc 1 . .
N N6 0.9503(8) -0.2524(8) 0.1575(4) 0.135(3) Uani d 1 . .
C C17 0.8632(7) -0.1693(7) 0.1446(4) 0.0883(18) 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 0.0181 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'
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
O2 S1 C22 . . 106.2(2) ?
O2 S1 C21 . . 106.3(2) ?
C21 S1 C22 . . 96.6(2) ?
C11 O1 C12 . . 116.6(2) ?
C11 N5 C8 . . 115.0(3) ?
C9 N3 C8 . . 117.2(3) ?
O1 C11 C10 . . 117.5(3) ?
N5 C11 O1 . . 118.1(3) ?
N5 C11 C10 . . 124.4(3) ?
C11 C10 Br1 . . 122.3(3) ?
C11 C10 C9 . . 116.3(3) ?
C9 C10 Br1 . . 121.4(2) ?
N5 C8 N3 . . 126.4(3) ?
N5 C8 N2 . . 119.8(3) ?
N3 C8 N2 . . 113.8(3) ?
C14 C12 O1 . . 118.7(3) ?
C19 C12 O1 . . 116.6(3) ?
C19 C12 C14 . . 124.6(3) ?
C8 N2 C5 . . 130.9(3) ?
C7 C6 C5 . . 119.9(3) ?
N3 C9 C10 . . 120.7(3) ?
N3 C9 N4 . . 116.7(3) ?
N4 C9 C10 . . 122.6(3) ?
C6 C5 N2 . . 125.4(3) ?
C6 C5 C4 . . 118.6(3) ?
C4 C5 N2 . . 116.0(3) ?
C12 C14 C13 . . 121.8(4) ?
C12 C14 C15 . . 116.7(4) ?
C15 C14 C13 . . 121.5(4) ?
C7 C2 C1 . . 120.3(3) ?
C7 C2 C3 . . 119.1(3) ?
C3 C2 C1 . . 120.6(3) ?
C12 C19 C18 . . 117.1(4) ?
C12 C19 C20 . . 121.2(4) ?
C18 C19 C20 . . 121.7(4) ?
C16 C18 C19 . . 120.5(4) ?
N1 C1 C2 . . 178.2(5) ?
C2 C7 C6 . . 121.3(3) ?
C18 C16 C15 . . 120.5(4) ?
C18 C16 C17 . . 119.0(5) ?
C15 C16 C17 . . 120.4(5) ?
C4 C3 C2 . . 119.9(3) ?
C3 C4 C5 . . 121.2(3) ?
C16 C15 C14 . . 120.6(4) ?
N6 C17 C16 . . 179.3(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
Br1 C10 . 1.878(3) ?
S1 O2 . 1.504(3) ?
S1 C22 . 1.781(5) ?
S1 C21 . 1.778(6) ?
O1 C11 . 1.364(4) ?
O1 C12 . 1.407(4) ?
N5 C11 . 1.329(4) ?
N5 C8 . 1.338(4) ?
N3 C8 . 1.341(4) ?
N3 C9 . 1.339(5) ?
C11 C10 . 1.369(4) ?
C10 C9 . 1.406(5) ?
C8 N2 . 1.359(4) ?
C12 C14 . 1.385(5) ?
C12 C19 . 1.379(5) ?
N2 C5 . 1.400(4) ?
C6 C5 . 1.392(4) ?
C6 C7 . 1.384(5) ?
C9 N4 . 1.352(4) ?
C5 C4 . 1.396(5) ?
C14 C13 . 1.495(6) ?
C14 C15 . 1.390(6) ?
C2 C1 . 1.439(5) ?
C2 C7 . 1.380(5) ?
C2 C3 . 1.391(5) ?
C19 C18 . 1.389(5) ?
C19 C20 . 1.512(6) ?
N1 C1 . 1.137(5) ?
C18 C16 . 1.386(7) ?
C16 C15 . 1.388(7) ?
C16 C17 . 1.436(6) ?
C3 C4 . 1.377(5) ?
N6 C17 . 1.139(6) ?

_cod_database_fobs_code 2022568
