Repurposing of the anti-HIV drug Emtricitabine as a hydrogen-bonded cleft for bipyridines via cocrystallization
Campillo-Alvarado, Gonzalo; Keene, Elizabeth; Swenson, Dale C.; MacGillivray, Len R.; CrystEngComm  (2020) –; doi:10.1039/D0CE00474J

data_7240473
_publ_section_title
;
 Repurposing of the anti-HIV drug Emtricitabine as a hydrogen-bonded cleft
 for bipyridines via cocrystallization
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00474J
_journal_year                    2020
_chemical_formula_moiety
'C8 H9 F N3 O3 S, C8 H10 F N3 O3 S, C10 H8 N4'
_chemical_formula_sum            'C26 H27 F2 N10 O6 S2'
_chemical_formula_weight         677.69
_chemical_name_systematic
'[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[4-azopyridine]''
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-03 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.538(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5024(8)
_cell_length_b                   11.2194(11)
_cell_length_c                   18.2134(18)
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.265
_cell_measurement_theta_min      2.2745
_cell_volume                     1507.2(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D-8 Venture Duo-Photon 3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32670
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.893
_diffrn_reflns_theta_min         2.275
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0713 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.9738. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       plate
_exptl_crystal_F_000             702
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         7064
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0487
_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/[\s^2^(Fo^2^)+(0.0514P)^2^+0.5135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                6093
_reflns_number_total             7064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00474j2.cif
_cod_data_source_block           FTC-apy
_cod_database_code               7240473
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N9-C19 \\sim N9B-C19
 with sigma of 0.02
 N9-N10 \\sim N9B-N10B
 with sigma of 0.02
 C24-N10 \\sim C24-N10B
 with sigma of 0.02
 N9-C24 \\sim N9B-C24
 with sigma of 0.04
 C19-N10 \\sim C19-N10B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(N10) = Uanis(N10B)
Uanis(N9B) = Uanis(N9)
4. Others
 Sof(N10B)=Sof(N9B)=1-FVAR(1)
 Sof(N9)=Sof(N10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C10(H10), C4(H4), C2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C3(H3C,H3D), C1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C22(H22), C9(H9), C17(H17), C23(H23), C26(H26), C18(H18),
 C21(H21), C20(H20), C25(H25)
5.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N6(H6A,H6B)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O1(H1)
;
_shelx_res_checksum              97927
_olex2_date_sample_data_collection 2019-09-17
_olex2_date_sample_submission    2019-09-03
_olex2_submission_original_sample_id FTC-apy
_olex2_submission_special_instructions 'No special instructions were received'