Base-Paired and Base-Stacked Structures of the Anti-HIV Drug Lamivudine: A Nucleoside DNA-Mimicry with Unprecedented Topology
Ellena, Javier; Bocelli, Marcio D.; Honorato, Sara B.; Ayala, Alejandro P.; Doriguetto, Antônio C.; Martins, Felipe T.; Crystal Growth & Design 12 (2012) 5138–; doi:10.1021/cg3011794

data_4506972
_publ_contact_author             'Martins, Felipe Terra'
_publ_section_title
;
 Base-Paired and Base-Stacked Structures of the Anti-HIV Drug Lamivudine:
 A Nucleoside DNA-Mimicry with Unprecedented Topology
;
_journal_issue                   10
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              5138
_journal_paper_doi               10.1021/cg3011794
_journal_volume                  12
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C8 H12 N3 O3 S, C8 H11 N3 O3 S, H2 O, Cl'
_chemical_formula_sum            'C16 H25 Cl N6 O7 S2'
_chemical_formula_weight         513.01
_chemical_name_common            'lamivudine hemihydrochloride hemihydrate'
_chemical_name_systematic
;
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-(1H)-pyrimidin-2-one
 hemihydrochloride hemihydrate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.52(3)
_cell_angle_beta                 93.15(4)
_cell_angle_gamma                91.43(4)
_cell_formula_units_Z            2
_cell_length_a                   6.972(5)
_cell_length_b                   12.167(7)
_cell_length_c                   13.867(8)
_cell_measurement_reflns_used    14026
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      2.910
_cell_volume                     1154.1(13)
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_sigmaI/netI    0.1401
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13168
_diffrn_reflns_theta_full        25.22
_diffrn_reflns_theta_max         25.22
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
   P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
   (1965), 18, 1035-1038
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         5394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1909
_refine_ls_R_factor_gt           0.1039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1454P)^2^+0.3557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2429
_refine_ls_wR_factor_ref         0.2912
_reflns_number_gt                2892
_reflns_number_total             5394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3011794_si_001.cif
_cod_data_source_block           CCDC787747
_cod_original_cell_volume        1153.9(12)
_cod_database_code               4506972