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_7240474
_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 unk
_chemical_formula_moiety         'C8 H10 F N3 O3 S, C10 H8 N2, 0.5(H2 O)'
_chemical_formula_sum            'C18 H19 F N5 O3.5 S'
_chemical_formula_weight         412.447
_chemical_name_systematic
'[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[4,4'-bipyridine]'
_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'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-28
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-02-03 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.087(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4668(10)
_cell_length_b                   9.6700(14)
_cell_length_c                   26.187(4)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.245
_cell_volume                     1890.8(5)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9933
_diffrn_measurement_device_type  'Bruker D-8 Venture Duo-Photon 3'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.9992
_diffrn_reflns_Laue_measured_fraction_max 0.9933
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            48450
_diffrn_reflns_point_group_measured_fraction_full 0.9977
_diffrn_reflns_point_group_measured_fraction_max 0.9901
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0949 before and 0.0706 after correction.
The Ratio of minimum to maximum transmission is 0.7869.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       irregular
_exptl_crystal_F_000             860.930
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.4154
_refine_diff_density_min         -0.3906
_refine_diff_density_rms         0.0777
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_d_res_high            0.7968
_refine_ls_d_res_low             9.0713
_refine_ls_goodness_of_fit_ref   1.0385
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    70
_refine_ls_number_parameters     508
_refine_ls_number_reflns         7767
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.0351
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+3.6194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.986
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              32
_reflns_limit_l_min              -32
_reflns_number_gt                7060
_reflns_number_total             7767
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0ce00474j2.cif
_cod_data_source_block           FTC-bipy
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_original_formula_moiety     '2(C8 H10 F N3 O3 S), 2(C10 H8 N2), H2 O'
_cod_original_formula_sum        'C36 H38 F2 N10 O7 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     824.895
_cod_database_code               7240474
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5000(16)
 0.5000(16)
2. 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, All O(H,H) groups
3. Rigid bond restraints
 H8, C29, C28, C27, N10, C31, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C29 \\sim C28 \\sim C27 \\sim N10 \\sim C31 \\sim C30: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
5.a Free rotating group:
 O7(H7a,H7b)
5.b Ternary CH refined with riding coordinates:
 C12(H12), C10(H10), C4(H4), C2(H2)
5.c Secondary CH2 refined with riding coordinates:
 C3(H3c,H3d), C11(H11a,H11b), C9(H9a,H9b), C1(H1a,H1b)
5.d Aromatic/amide H refined with riding coordinates:
 C24(H24), C16(H16), C21(H21), C28(H28), C27(H27), C31(H31), C30(H30),
 C20(H20), C35(H35), C18(H18), C33(H33), C32(H32), C23(H23), C25(H25), C8(H8),
 C26(H26), C36(H36), C17(H17)
5.e Fitted hexagon refined as free rotating group:
 C29(C28,C27,N10,C31,C30)
5.f X=CH2 refined with riding coordinates:
 N3(H3a,H3b), N6(H6a,H6b)
5.g Idealised tetrahedral OH refined as rotating group:
 O4(H4a), O1(H1)
;
_olex2_date_sample_data_collection 2020-01-08
_olex2_date_sample_submission    2020-01-07
_olex2_submission_original_sample_id FTC-bipy
_olex2_submission_special_instructions 'No special instructions were received'