#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/78/1557814.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1557814
loop_
_publ_author_name
'Rudd, Nathan D.'
'Reibarkh, Mikhail'
'Fang, Rui'
'Mittal, Sachin'
'Walsh, Paul L.'
'Brunskill, Andrew P. J.'
'Forrest, William P.'
_publ_section_title
;
 Interpreting in vitro Release Performance from Long-Acting
 Parenteral Nanosuspensions using USP-4 Dissolution and Spectroscopic
 Techniques.
;
_journal_name_full               'Molecular pharmaceutics'
_journal_paper_doi               10.1021/acs.molpharmaceut.0c00208
_journal_year                    2020
_chemical_formula_moiety         'C17 H11 Cl F3 N5 O3'
_chemical_formula_sum            'C17 H11 Cl F3 N5 O3'
_chemical_formula_weight         425.76
_chemical_name_common            doravirine
_chemical_name_systematic
;
3-Chloro-5-({1-[(4-methyl-5-oxo-4,5-dihydro-1H
-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)
-1,2-dihydropyridin-3-yl}oxy)benzonitrile
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                101.878(2)
_cell_angle_beta                 104.712(2)
_cell_angle_gamma                97.380(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9899(5)
_cell_length_b                   10.1223(6)
_cell_length_c                   11.6441(7)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.66
_cell_measurement_theta_min      4.05
_cell_volume                     874.95(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14023
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.659
_diffrn_reflns_theta_min         4.052
_diffrn_source                   'sealed-tube microsource X-ray generator'
_exptl_absorpt_coefficient_mu    2.525
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
(SADABS; Sheldrick, 2003) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0472P)²+1.2321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3045
_reflns_number_total             3075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mp0c00208_si_002.cif
_cod_data_source_block           mdk011_abs
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1557814
_shelx_shelxl_version_number     2014/7
_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   0.751
_shelx_estimated_absorpt_t_max   0.786
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3695(2) 0.54365(17) 0.74347(15) 0.0144(4) Uani 1 1 d . . . . .
C2 C 0.2647(3) 0.5627(2) 0.82175(19) 0.0153(4) Uani 1 1 d . . . . .
O2 O 0.29871(19) 0.53250(15) 0.92105(13) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.1110(3) 0.6205(2) 0.77487(19) 0.0161(4) Uani 1 1 d . . . . .
O3 O -0.00269(19) 0.63329(15) 0.84673(13) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.0756(3) 0.6536(2) 0.66545(19) 0.0172(4) Uani 1 1 d . . . . .
C4A C -0.0826(3) 0.7170(2) 0.6244(2) 0.0243(5) Uani 1 1 d . . . . .
F4A F -0.23231(17) 0.64165(16) 0.62456(13) 0.0317(3) Uani 1 1 d . . . . .
F4B F -0.0655(2) 0.84069(16) 0.69749(16) 0.0486(5) Uani 1 1 d . . . . .
F4C F -0.10735(19) 0.73244(16) 0.51029(14) 0.0332(4) Uani 1 1 d . . . . .
C5 C 0.1920(3) 0.6332(2) 0.5923(2) 0.0183(4) Uani 1 1 d . . . . .
H5A H 0.1699 0.6567 0.5157 0.022 Uiso 1 1 calc R U . . .
C6 C 0.3352(3) 0.5794(2) 0.63409(19) 0.0163(4) Uani 1 1 d . . . . .
H6A H 0.4143 0.5661 0.5860 0.020 Uiso 1 1 calc R U . . .
C7 C 0.5318(3) 0.4883(2) 0.78341(19) 0.0159(4) Uani 1 1 d . . . . .
H7A H 0.5528 0.4853 0.8703 0.019 Uiso 1 1 calc R U . . .
H7B H 0.6340 0.5499 0.7770 0.019 Uiso 1 1 calc R U . . .
C8 C 0.5156(3) 0.3467(2) 0.70616(19) 0.0156(4) Uani 1 1 d . . . . .
N9 N 0.5596(2) 0.32260(18) 0.60487(17) 0.0180(4) Uani 1 1 d . . . . .
N10 N 0.5162(2) 0.18124(18) 0.56183(16) 0.0186(4) Uani 1 1 d . . . . .
H10A H 0.5301 0.1364 0.4927 0.022 Uiso 1 1 calc R U . . .
C11 C 0.4498(3) 0.1191(2) 0.6376(2) 0.0181(4) Uani 1 1 d . . . . .
O11 O 0.4049(2) -0.00513(15) 0.62883(15) 0.0234(4) Uani 1 1 d . . . . .
N12 N 0.4465(2) 0.22772(18) 0.73067(16) 0.0168(4) Uani 1 1 d . . . . .
C12A C 0.3992(3) 0.2111(2) 0.8404(2) 0.0220(5) Uani 1 1 d . . . . .
H12A H 0.3303 0.1185 0.8247 0.033 Uiso 1 1 calc R U . . .
H12B H 0.3287 0.2794 0.8622 0.033 Uiso 1 1 calc R U . . .
H12C H 0.5066 0.2241 0.9081 0.033 Uiso 1 1 calc R U . . .
C1' C 0.0651(3) 0.7281(2) 0.96012(19) 0.0170(4) Uani 1 1 d . . . . .
C2' C 0.0140(3) 0.6941(2) 1.0569(2) 0.0182(4) Uani 1 1 d . . . . .
H2'A H -0.0622 0.6095 1.0460 0.022 Uiso 1 1 calc R U . . .
C3' C 0.0777(3) 0.7880(2) 1.1705(2) 0.0190(4) Uani 1 1 d . . . . .
Cl3' Cl 0.01893(7) 0.74769(6) 1.29585(5) 0.02901(18) Uani 1 1 d . . . . .
C4' C 0.1869(3) 0.9126(2) 1.1891(2) 0.0195(5) Uani 1 1 d . . . . .
H4'A H 0.2295 0.9749 1.2678 0.023 Uiso 1 1 calc R U . . .
C5' C 0.2322(3) 0.9439(2) 1.0890(2) 0.0207(5) Uani 1 1 d . . . . .
C5A' C 0.3496(3) 1.0795(3) 1.1044(2) 0.0247(5) Uani 1 1 d . . . . .
N5A' N 0.4298(4) 1.1705(3) 1.1140(2) 0.0485(7) Uani 1 1 d . . . . .
C6' C 0.1725(3) 0.8522(2) 0.9731(2) 0.0197(5) Uani 1 1 d . . . . .
H6'A H 0.2047 0.8744 0.9053 0.024 Uiso 1 1 calc R U . . .
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 123.29(18) . . ?
C6 N1 C7 118.29(17) . . ?
C2 N1 C7 118.34(17) . . ?
O2 C2 N1 122.69(19) . . ?
O2 C2 C3 123.48(19) . . ?
N1 C2 C3 113.82(18) . . ?
C4 C3 O3 121.52(19) . . ?
C4 C3 C2 122.78(19) . . ?
O3 C3 C2 115.63(18) . . ?
C3 O3 C1' 115.48(16) . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 C4A 119.9(2) . . ?
C5 C4 C4A 120.4(2) . . ?
F4B C4A F4A 107.02(19) . . ?
F4B C4A F4C 107.3(2) . . ?
F4A C4A F4C 106.04(18) . . ?
F4B C4A C4 110.96(19) . . ?
F4A C4A C4 112.77(19) . . ?
F4C C4A C4 112.40(19) . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C5 C6 N1 121.96(19) . . ?
C5 C6 H6A 119.0 . . ?
N1 C6 H6A 119.0 . . ?
N1 C7 C8 110.89(16) . . ?
N1 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
N9 C8 N12 111.99(18) . . ?
N9 C8 C7 123.53(19) . . ?
N12 C8 C7 124.43(19) . . ?
C8 N9 N10 104.20(17) . . ?
C11 N10 N9 112.68(17) . . ?
C11 N10 H10A 123.7 . . ?
N9 N10 H10A 123.7 . . ?
O11 C11 N10 129.1(2) . . ?
O11 C11 N12 127.2(2) . . ?
N10 C11 N12 103.71(18) . . ?
C8 N12 C11 107.39(17) . . ?
C8 N12 C12A 128.26(18) . . ?
C11 N12 C12A 123.87(18) . . ?
N12 C12A H12A 109.5 . . ?
N12 C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
N12 C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C2' C1' C6' 122.1(2) . . ?
C2' C1' O3 116.66(19) . . ?
C6' C1' O3 121.15(19) . . ?
C1' C2' C3' 117.7(2) . . ?
C1' C2' H2'A 121.1 . . ?
C3' C2' H2'A 121.1 . . ?
C4' C3' C2' 122.6(2) . . ?
C4' C3' Cl3' 118.27(17) . . ?
C2' C3' Cl3' 119.15(17) . . ?
C3' C4' C5' 117.9(2) . . ?
C3' C4' H4'A 121.1 . . ?
C5' C4' H4'A 121.1 . . ?
C4' C5' C6' 121.6(2) . . ?
C4' C5' C5A' 119.8(2) . . ?
C6' C5' C5A' 118.6(2) . . ?
N5A' C5A' C5' 179.2(3) . . ?
C1' C6' C5' 118.1(2) . . ?
C1' C6' H6'A 121.0 . . ?
C5' C6' H6'A 121.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.366(3) . ?
N1 C2 1.388(3) . ?
N1 C7 1.483(3) . ?
C2 O2 1.230(3) . ?
C2 C3 1.457(3) . ?
C3 C4 1.354(3) . ?
C3 O3 1.384(2) . ?
O3 C1' 1.392(3) . ?
C4 C5 1.419(3) . ?
C4 C4A 1.505(3) . ?
C4A F4B 1.330(3) . ?
C4A F4A 1.334(3) . ?
C4A F4C 1.338(3) . ?
C5 C6 1.351(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.497(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N9 1.299(3) . ?
C8 N12 1.374(3) . ?
N9 N10 1.381(3) . ?
N10 C11 1.354(3) . ?
N10 H10A 0.8800 . ?
C11 O11 1.239(3) . ?
C11 N12 1.384(3) . ?
N12 C12A 1.457(3) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C1' C2' 1.382(3) . ?
C1' C6' 1.384(3) . ?
C2' C3' 1.389(3) . ?
C2' H2'A 0.9500 . ?
C3' C4' 1.381(3) . ?
C3' Cl3' 1.750(2) . ?
C4' C5' 1.388(3) . ?
C4' H4'A 0.9500 . ?
C5' C6' 1.397(3) . ?
C5' C5A' 1.509(3) . ?
C5A' N5A' 1.021(4) . ?
C6' H6'A 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10A O11 0.88 1.95 2.806(2) 162.9 2_656
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 O2 -178.60(19) . . . . ?
C7 N1 C2 O2 -1.8(3) . . . . ?
C6 N1 C2 C3 1.9(3) . . . . ?
C7 N1 C2 C3 178.64(17) . . . . ?
O2 C2 C3 C4 179.8(2) . . . . ?
N1 C2 C3 C4 -0.7(3) . . . . ?
O2 C2 C3 O3 -3.3(3) . . . . ?
N1 C2 C3 O3 176.20(16) . . . . ?
C4 C3 O3 C1' -116.5(2) . . . . ?
C2 C3 O3 C1' 66.6(2) . . . . ?
O3 C3 C4 C5 -177.24(18) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
O3 C3 C4 C4A 5.2(3) . . . . ?
C2 C3 C4 C4A -178.13(19) . . . . ?
C3 C4 C4A F4B 65.2(3) . . . . ?
C5 C4 C4A F4B -112.3(2) . . . . ?
C3 C4 C4A F4A -54.8(3) . . . . ?
C5 C4 C4A F4A 127.6(2) . . . . ?
C3 C4 C4A F4C -174.62(19) . . . . ?
C5 C4 C4A F4C 7.8(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4A C4 C5 C6 178.2(2) . . . . ?
C4 C5 C6 N1 0.5(3) . . . . ?
C2 N1 C6 C5 -1.9(3) . . . . ?
C7 N1 C6 C5 -178.65(19) . . . . ?
C6 N1 C7 C8 -70.9(2) . . . . ?
C2 N1 C7 C8 112.2(2) . . . . ?
N1 C7 C8 N9 88.7(2) . . . . ?
N1 C7 C8 N12 -88.6(2) . . . . ?
N12 C8 N9 N10 0.2(2) . . . . ?
C7 C8 N9 N10 -177.33(18) . . . . ?
C8 N9 N10 C11 -1.4(2) . . . . ?
N9 N10 C11 O11 -176.9(2) . . . . ?
N9 N10 C11 N12 2.0(2) . . . . ?
N9 C8 N12 C11 1.0(2) . . . . ?
C7 C8 N12 C11 178.50(18) . . . . ?
N9 C8 N12 C12A 173.17(19) . . . . ?
C7 C8 N12 C12A -9.3(3) . . . . ?
O11 C11 N12 C8 177.1(2) . . . . ?
N10 C11 N12 C8 -1.7(2) . . . . ?
O11 C11 N12 C12A 4.5(3) . . . . ?
N10 C11 N12 C12A -174.34(18) . . . . ?
C3 O3 C1' C2' -143.66(19) . . . . ?
C3 O3 C1' C6' 38.9(3) . . . . ?
C6' C1' C2' C3' -1.6(3) . . . . ?
O3 C1' C2' C3' -179.02(18) . . . . ?
C1' C2' C3' C4' 0.8(3) . . . . ?
C1' C2' C3' Cl3' -178.98(15) . . . . ?
C2' C3' C4' C5' 0.4(3) . . . . ?
Cl3' C3' C4' C5' -179.75(16) . . . . ?
C3' C4' C5' C6' -1.0(3) . . . . ?
C3' C4' C5' C5A' 179.4(2) . . . . ?
C2' C1' C6' C5' 1.1(3) . . . . ?
O3 C1' C6' C5' 178.38(18) . . . . ?
C4' C5' C6' C1' 0.3(3) . . . . ?
C5A' C5' C6' C1' 179.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 58460047
