Why lamivudine assembles into double-stranded helices in crystals: salt heterosynthon versus base-pairing homosynthon
da Silva, Cameron Capeletti; Valdo, Ana K.; do Nascimento Neto, José Antônio; Ribeiro, Leandro; Sarotti, Ariel M.; Martins, Felipe Terra; CrystEngComm 20 (2018) 3049–; doi:10.1039/C8CE00100F

data_7230545
_publ_section_title
;
 Why lamivudine assembles into double-stranded helices in crystals: salt
 heterosynthon versus base-pairing homosynthon
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3049
_journal_paper_doi               10.1039/C8CE00100F
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C8 H12 N3 O3 S, H O4 S'
_chemical_formula_sum            'C8 H13 N3 O7 S2'
_chemical_formula_weight         327.33
_chemical_name_common            'lamivudine hydrogen sulfate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-02-22 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.756(2)
_cell_length_b                   10.726(3)
_cell_length_c                   23.809(8)
_cell_measurement_reflns_used    171
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.95
_cell_measurement_theta_min      3.47
_cell_volume                     1725.3(9)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5046
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.528
_diffrn_reflns_theta_min         1.711
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details
;
 Flack x determined using 627 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0839
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1656P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2231
_refine_ls_wR_factor_ref         0.2463
_reflns_Friedel_coverage         0.590
_reflns_Friedel_fraction_full    0.809
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                2080
_reflns_number_total             2833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00100f2.cif
_cod_data_source_block           shelxl_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7230543--7230547.cif.'
_cod_database_code               7230545
_shelxl_version_number           2014-3
_shelx_res_checksum              45136