#------------------------------------------------------------------------------
#$Date: 2022-02-22 04:56:09 +0200 (Tue, 22 Feb 2022) $
#$Revision: 273079 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/25/2022567.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_2022567
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      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
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.116(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2801(6)
_cell_length_b                   15.4330(9)
_cell_length_c                   17.1702(11)
_cell_measurement_reflns_used    3301
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2730
_cell_measurement_theta_min      3.8610
_cell_volume                     2449.3(3)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_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
;
SHELXD (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.4335
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type
'Agilent 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  0.0461
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.665
_diffrn_reflns_theta_min         3.858
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       needle
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.754
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1282P)²+0.5303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1838
_refine_ls_wR_factor_ref         0.2136
_reflns_number_gt                3590
_reflns_number_total             4663
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3022sup1.cif
_cod_data_source_block           ETR-DMSO1
_cod_database_code               2022567
_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
Br Br1 0.63939(6) 0.45526(3) 0.18484(3) 0.0815(3) Uani d 1 . .
C C8 0.9723(4) 0.2995(2) 0.0659(2) 0.0527(8) Uani d 1 . .
C C5 1.1080(4) 0.1658(2) 0.0405(2) 0.0576(8) Uani d 1 . .
C C14 0.6383(4) 0.1208(3) 0.1788(2) 0.0658(10) Uani d 1 . .
N N2 1.0728(4) 0.2528(2) 0.0300(2) 0.0620(8) Uani d 1 . .
H H2 1.119750 0.280629 -0.002984 0.074 Uiso calc 1 . .
O O1 0.7168(3) 0.26599(19) 0.20069(18) 0.0690(8) Uani d 1 . .
N N5 0.8938(3) 0.25682(19) 0.11601(18) 0.0563(7) Uani d 1 . .
C C9 0.8612(4) 0.4301(2) 0.0802(2) 0.0557(8) Uani d 1 . .
C C11 0.7983(4) 0.3043(2) 0.1491(2) 0.0549(8) Uani d 1 . .
C C12 0.7374(4) 0.1778(3) 0.2155(2) 0.0605(9) Uani d 1 . .
C C15 0.6485(5) 0.0339(3) 0.2002(3) 0.0701(11) Uani d 1 . .
H H15 0.582808 -0.005979 0.177087 0.084 Uiso calc 1 . .
O O2 0.7257(3) -0.3226(2) 0.0764(2) 0.0801(9) Uani d 1 . .
C C4 1.1572(5) 0.1216(3) -0.0229(2) 0.0670(10) Uani d 1 . .
H H4 1.162758 0.150434 -0.070126 0.080 Uiso calc 1 . .
N N3 0.9605(3) 0.38274(19) 0.04555(18) 0.0567(7) Uani d 1 . .
C C19 0.8458(5) 0.1525(3) 0.2726(2) 0.0667(10) Uani d 1 . .
C C2 1.1918(5) -0.0074(3) 0.0534(3) 0.0701(10) Uani d 1 . .
C C3 1.1975(5) 0.0363(3) -0.0168(3) 0.0725(11) Uani d 1 . .
H H3 1.228743 0.007674 -0.059823 0.087 Uiso calc 1 . .
C C10 0.7788(4) 0.3912(2) 0.1352(2) 0.0566(8) Uani d 1 . .
C C18 0.8538(5) 0.0655(3) 0.2916(3) 0.0752(11) Uani d 1 . .
H H18 0.925508 0.046191 0.328860 0.090 Uiso calc 1 . .
N N4 0.8474(4) 0.5133(2) 0.0595(2) 0.0708(9) Uani d 1 . .
H H4A 0.900290 0.534518 0.025454 0.085 Uiso calc 1 . .
H H4B 0.785658 0.545688 0.080073 0.085 Uiso calc 1 . .
C C7 1.1442(5) 0.0366(3) 0.1171(3) 0.0778(13) Uani d 1 . .
H H7 1.139613 0.007752 0.164372 0.093 Uiso calc 1 . .
C C1 1.2338(6) -0.0970(3) 0.0588(4) 0.0881(14) Uani d 1 . .
C C6 1.1040(5) 0.1220(3) 0.1108(2) 0.0702(11) Uani d 1 . .
H H6 1.073745 0.150859 0.153995 0.084 Uiso calc 1 . .
N N6 0.7769(8) -0.1550(4) 0.2933(4) 0.142(3) Uani d 1 . .
C C13 0.5237(6) 0.1517(4) 0.1184(3) 0.0937(16) Uani d 1 . .
H H13A 0.466595 0.195659 0.140560 0.141 Uiso calc 1 . .
H H13B 0.462604 0.103992 0.101089 0.141 Uiso calc 1 . .
H H13C 0.568280 0.175314 0.074713 0.141 Uiso calc 1 . .
C C20 0.9503(6) 0.2166(4) 0.3120(3) 0.0905(15) Uani d 1 . .
H H20A 1.007268 0.241892 0.273963 0.136 Uiso calc 1 . .
H H20B 1.012732 0.187493 0.351276 0.136 Uiso calc 1 . .
H H20C 0.897531 0.261268 0.336076 0.136 Uiso calc 1 . .
C C21 0.5375(8) -0.2815(6) 0.1709(4) 0.126(3) Uani d 1 . .
H H21A 0.576751 -0.333106 0.195805 0.190 Uiso calc 1 . .
H H21B 0.434243 -0.281425 0.171819 0.190 Uiso calc 1 . .
H H21C 0.577519 -0.231560 0.198174 0.190 Uiso calc 1 . .
N N1 1.2702(7) -0.1671(3) 0.0641(4) 0.122(2) Uani d 1 . .
S S1 0.58124(13) -0.27884(7) 0.07405(6) 0.0692(3) Uani d 1 . .
C C17 0.7680(7) -0.0842(4) 0.2766(4) 0.0975(16) Uani d 1 . .
C C16 0.7562(5) 0.0066(3) 0.2559(3) 0.0748(11) Uani d 1 . .
C C22 0.4522(8) -0.3545(5) 0.0378(5) 0.145(3) Uani d 1 . .
H H22A 0.471265 -0.371208 -0.014164 0.217 Uiso calc 1 . .
H H22B 0.357508 -0.329286 0.036623 0.217 Uiso calc 1 . .
H H22C 0.457013 -0.404670 0.071013 0.217 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'
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
N5 C8 N2 . . 117.3(3) ?
N3 C8 N2 . . 115.7(3) ?
N3 C8 N5 . . 127.0(3) ?
N2 C5 C4 . . 117.5(3) ?
C6 C5 N2 . . 123.9(3) ?
C6 C5 C4 . . 118.5(4) ?
C12 C14 C15 . . 117.8(4) ?
C12 C14 C13 . . 121.1(4) ?
C15 C14 C13 . . 121.2(4) ?
C8 N2 C5 . . 127.8(3) ?
C11 O1 C12 . . 118.1(3) ?
C11 N5 C8 . . 115.2(3) ?
N3 C9 C10 . . 119.8(3) ?
N4 C9 N3 . . 117.0(3) ?
N4 C9 C10 . . 123.1(3) ?
O1 C11 C10 . . 118.0(3) ?
N5 C11 O1 . . 118.5(3) ?
N5 C11 C10 . . 123.5(3) ?
C14 C12 O1 . . 117.5(4) ?
C14 C12 C19 . . 123.4(4) ?
O1 C12 C19 . . 118.6(4) ?
C16 C15 C14 . . 120.2(4) ?
C3 C4 C5 . . 121.0(4) ?
C8 N3 C9 . . 116.6(3) ?
C12 C19 C20 . . 121.9(4) ?
C18 C19 C12 . . 117.2(4) ?
C18 C19 C20 . . 120.9(4) ?
C3 C2 C7 . . 119.0(4) ?
C3 C2 C1 . . 119.6(4) ?
C7 C2 C1 . . 121.4(4) ?
C4 C3 C2 . . 120.3(4) ?
C9 C10 Br1 . . 121.1(3) ?
C11 C10 Br1 . . 121.1(3) ?
C11 C10 C9 . . 117.7(3) ?
C19 C18 C16 . . 120.9(4) ?
C6 C7 C2 . . 120.6(4) ?
N1 C1 C2 . . 178.2(8) ?
C7 C6 C5 . . 120.6(4) ?
O2 S1 C21 . . 104.3(3) ?
O2 S1 C22 . . 107.0(3) ?
C21 S1 C22 . . 96.5(5) ?
N6 C17 C16 . . 179.5(8) ?
C15 C16 C18 . . 120.5(4) ?
C15 C16 C17 . . 119.9(5) ?
C18 C16 C17 . . 119.6(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 C10 . 1.891(3) ?
C8 N2 . 1.368(4) ?
C8 N5 . 1.348(4) ?
C8 N3 . 1.333(5) ?
C5 N2 . 1.390(5) ?
C5 C4 . 1.396(5) ?
C5 C6 . 1.386(5) ?
C14 C12 . 1.383(6) ?
C14 C15 . 1.391(6) ?
C14 C13 . 1.497(6) ?
O1 C11 . 1.351(4) ?
O1 C12 . 1.395(5) ?
N5 C11 . 1.318(5) ?
C9 N3 . 1.355(5) ?
C9 C10 . 1.402(5) ?
C9 N4 . 1.335(5) ?
C11 C10 . 1.372(5) ?
C12 C19 . 1.396(6) ?
C15 C16 . 1.386(7) ?
O2 S1 . 1.499(3) ?
C4 C3 . 1.368(6) ?
C19 C18 . 1.382(7) ?
C19 C20 . 1.503(7) ?
C2 C3 . 1.386(6) ?
C2 C7 . 1.392(6) ?
C2 C1 . 1.438(6) ?
C18 C16 . 1.387(7) ?
C7 C6 . 1.373(6) ?
C1 N1 . 1.135(7) ?
N6 C17 . 1.130(7) ?
C21 S1 . 1.746(6) ?
S1 C22 . 1.747(7) ?
C17 C16 . 1.447(7) ?

_cod_database_fobs_code 2022567
