Crystal structure and Hirshfeld surface analysis of the anhydrous form of the nucleoside analogue entecavir
Wang, Xiaojuan; Xu, Hai-Jiang; Jia, Xue-Dong; Yang, Yan-Tao; Zhang, Xiao-Jian; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618002528

data_2021045
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of the anhydrous form of
 the nucleoside analogue entecavir
;
_journal_coeditor_code           SK3678
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618002528
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C12 H15 N5 O3'
_chemical_formula_moiety         'C12 H15 N5 O3'
_chemical_formula_sum            'C12 H15 N5 O3'
_chemical_formula_weight         277.29
_chemical_name_common
;
Entecavir
;
_chemical_name_systematic
2-Amino-9-[(1<i>S</i>,3<i>R</i>,4<i>S</i>)-4-hydroxy-3-hydroxymethyl-2-methylenecyclopentyl]-1,9-dihydro-6<i>H</i>-purin-6-one
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.559(2)
_cell_length_b                   7.559(2)
_cell_length_c                   44.103(12)
_cell_measurement_reflns_used    3656
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.59
_cell_measurement_theta_min      2.73
_cell_volume                     2520.0(12)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>, 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            9930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_min         2.734
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.282
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0650P)^2^+1.0490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                2251
_reflns_number_total             2865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3678sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2520.0(15)
_cod_database_code               2021045
_cod_database_fobs_code          2021045
_shelx_hkl_checksum              48014
_shelx_res_checksum              75321