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_7240471
_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_absolute_configuration syn
_chemical_formula_moiety         '2(C8 H10 F N3 O3 S), C12 H12 N2'
_chemical_formula_sum            'C28 H32 F2 N8 O6 S2'
_chemical_formula_weight         678.73
_chemical_name_systematic
'[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[1,2-Bis(4-pyridyl)ethane]'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-13
_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                 99.640(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6333(8)
_cell_length_b                   11.2359(11)
_cell_length_c                   18.1058(18)
_cell_measurement_reflns_used    6823
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.9145
_cell_volume                     1531.0(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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0313
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15295
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.756
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1097 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.9521. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       needle
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 2112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5271
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+0.2269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0700
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4924
_reflns_number_total             5271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00474j2.cif
_cod_data_source_block           FTC-bpeta
_cod_database_code               7240471
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22A) = Uanis(C22B)
Uanis(C23A) = Uanis(C23B)
3. Others
 Sof(C23B)=Sof(H23A)=Sof(H23B)=Sof(C22B)=Sof(H22A)=Sof(H22B)=1-FVAR(1)
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C12(H12), C2(H2), C10(H10), C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C1(H1A,H1B), C3(H3C,H3D), C9(H9A,H9B), C23B(H23A,H23B),
 C22B(H22A,H22B), C22A(H22C,H22D), C23A(H23C,H23D)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C24(H24), C21(H21), C20(H20), C17(H17), C18(H18), C27(H27),
 C25(H25), C28(H28)
;
_shelx_res_checksum              3499
_olex2_submission_original_sample_id EMT-bpeta
_olex2_submission_special_instructions 'No special instructions were received'