Synthesis of activated 3'-amino-3'-deoxy-2-thio-thymidine, a superior substrate for the nonenzymatic copying of nucleic acid templates.
Izgu, Enver Cagri; Oh, Seung Soo; Szostak, Jack W.; Chemical communications (Cambridge, England) 52 (2016) 3684–3686; doi:10.1039/c5cc10317g

data_7118677
_publ_section_title
;
 Synthesis of activated 3'-amino-3'-deoxy-2-thio-thymidine, a superior
 substrate for the nonenzymatic copying of nucleic acid templates.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3684
_journal_page_last               3686
_journal_paper_doi               10.1039/c5cc10317g
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         C12H17N3O4S?CHCl3
_chemical_formula_sum            'C13 H18 Cl3 N3 O4 S'
_chemical_formula_weight         418.71
_chemical_name_common            ECI5017
_chemical_name_systematic
' [(2S,3S,5R)-3-amino-5-(5-methyl-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl acetate'
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-04 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9957(3)
_cell_length_b                   17.7935(9)
_cell_length_c                   20.4746(10)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.29
_cell_volume                     1820.01(17)
_computing_cell_refinement       'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_data_collection       'APEX3 v2015.5.2 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15691
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.608
_diffrn_reflns_theta_min         3.291
_exptl_absorpt_coefficient_mu    5.847
_exptl_absorpt_correction_T_max  0.8146
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 930 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       0.0038(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0790
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0929P)^2^+8.8958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2142
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2776
_reflns_number_total             3129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc10317g2.cif
_cod_data_source_block           ECI5017
_cod_depositor_comments          'Adding full bibliography for 7118677.cif.'
_cod_database_code               7118677
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.540
_shelx_estimated_absorpt_t_max   0.955
_shelx_res_checksum              27460