Asymmetric Synthesis of 2'-<i>C</i>-Methyl-4'-selenonucleosides as Anti-Hepatitis C Virus Agents.
Lee, Hyejin; Jarhad, Dnyandev B.; Yu, Jinha; Lee, Choongho; Jeong, Lak Shin; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b01462

data_4033650
_publ_section_title
;
 Asymmetric Synthesis of 2'-<i>C</i>-Methyl-4'-selenonucleosides as
 Anti-Hepatitis C Virus Agents.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01462
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C11 H13 Cl N4 O3 Se'
_chemical_formula_sum            'C11 H13 Cl N4 O3 Se'
_chemical_formula_weight         363.66
_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     dual
_audit_creation_date             2019-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5314(2)
_cell_length_b                   7.9755(2)
_cell_length_c                   22.8076(5)
_cell_measurement_reflns_used    7822
_cell_measurement_temperature    293.44(16)
_cell_measurement_theta_max      73.5280
_cell_measurement_theta_min      3.8420
_cell_volume                     1369.98(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.44(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -113.00 -88.00   1.00    1.00    --  -41.49 -38.00  60.00   25
  2  \w   -116.00 -18.00   1.00    1.00    --  -41.49 -37.00 168.00   98
  3  \w    -64.00 -24.00   1.00    1.00    --  -41.49 -38.00  60.00   40
  4  \w     55.00  82.00   1.00    1.00    --   41.49  38.00-180.00   27
  5  \w     34.00  82.00   1.00    1.00    --   41.49-125.00-180.00   48
  6  \w     15.00 116.00   1.00    1.00    --   41.49  77.00  90.00  101
  7  \w      2.00  70.00   1.00    1.00    --   41.49 -99.00 -30.00   68
  8  \w     83.00 173.00   1.00    1.00    --  106.19  61.00 120.00   90
  9  \w    110.00 178.00   1.00    1.00    --  106.19  77.00   0.00   68
 10  \w    133.00 160.00   1.00    1.00    --  106.19  61.00  90.00   27
 11  \w     78.00 130.00   1.00    1.00    --  106.19  61.00  60.00   52
 12  \w     31.00  97.00   1.00    1.00    --  106.19 -94.00 -30.00   66
 13  \w    147.00 178.00   1.00    1.00    --  106.19 112.00-178.00   31
 14  \w     82.00 109.00   1.00    1.00    --  106.19  61.00   0.00   27
 15  \w     74.00 101.00   1.00    1.00    --  106.19  77.00  60.00   27
 16  \w    111.00 178.00   1.00    1.00    --  106.19  30.00-180.00   67
 17  \w     75.00 101.00   1.00    1.00    --  106.19  77.00   0.00   26
 18  \w     64.00 108.00   1.00    1.00    --  106.19 -94.00-150.00   44
 19  \w     77.00 104.00   1.00    1.00    --  106.19  61.00  30.00   27
 20  \w     75.00 101.00   1.00    1.00    --  106.19  77.00  90.00   26
 21  \w    112.00 178.00   1.00    1.00    --  106.19 125.00  30.00   66
 22  \w    114.00 172.00   1.00    1.00    --  106.19  77.00  60.00   58
 23  \w     80.00 106.00   1.00    1.00    --  106.19  30.00  30.00   26
 24  \w     81.00 108.00   1.00    1.00    --  106.19  45.00  90.00   27
 25  \w     82.00 109.00   1.00    1.00    --  106.19  45.00 120.00   27
 26  \w     25.00  59.00   1.00    1.00    --  106.19 -94.00-150.00   34
 27  \w     74.00 101.00   1.00    1.00    --  106.19  77.00  30.00   27
 28  \w     81.00 106.00   1.00    1.00    --  106.19  45.00  30.00   25
 29  \w     46.00 104.00   1.00    1.00    --  106.19-125.00-180.00   58
 30  \w     77.00 103.00   1.00    1.00    --  106.19  61.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '/w scans with narrow frames'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0393119000
_diffrn_orient_matrix_UB_12      0.1319471000
_diffrn_orient_matrix_UB_13      0.0476303000
_diffrn_orient_matrix_UB_21      -0.0894099000
_diffrn_orient_matrix_UB_22      0.1126605000
_diffrn_orient_matrix_UB_23      -0.0462338000
_diffrn_orient_matrix_UB_31      -0.1796516000
_diffrn_orient_matrix_UB_32      -0.0849496000
_diffrn_orient_matrix_UB_33      0.0125822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11293
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.671
_diffrn_reflns_theta_min         3.876
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.647
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_description       irregular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.114
_refine_diff_density_max         1.548
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Flack x determined using 1076 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0753P)^2^+1.5918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2681
_reflns_number_total             2734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01462_si_004.cif
_cod_data_source_block           exp_1212
_cod_database_code               4033650
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C11 H13 Cl N4 O3 Se'
_chemical_oxdiff_usercomment     6-Cl-Purine
_shelx_estimated_absorpt_t_max   0.565
_shelx_estimated_absorpt_t_min   0.240
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C13(H13), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O17(H17), O18(H18), O16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.656