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_4033649
_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 H14 Cl N5 O3 Se'
_chemical_formula_sum            'C11 H14 Cl N5 O3 Se'
_chemical_formula_weight         378.68
_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
_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                   7.51500(10)
_cell_length_b                   7.71360(10)
_cell_length_c                   24.1346(3)
_cell_measurement_reflns_used    4096
_cell_measurement_temperature    292.82(10)
_cell_measurement_theta_max      73.3140
_cell_measurement_theta_min      3.6670
_cell_volume                     1399.03(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.82(10)
_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 0.978
_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   -102.00 -76.00   1.00    1.00    --  -41.24-158.00-149.00   26
  2  \w   -109.00  45.00   1.00    1.00    --  -41.24   0.00  30.00  154
  3  \w     94.00 168.00   1.00    1.00    --  106.19  45.00 -90.00   74
  4  \w     92.00 120.00   1.00    1.00    --  106.19-125.00   0.00   28
  5  \w     54.00 134.00   1.00    1.00    --  106.19 -30.00  90.00   80
  6  \w     94.00 158.00   1.00    1.00    --  106.19 125.00 -90.00   64
  7  \w     40.00  73.00   1.00    1.00    --  106.19-125.00   0.00   33
  8  \w    136.00 176.00   1.00    1.00    --  106.19 125.00-180.00   40
  9  \w    101.00 178.00   1.00    1.00    --  106.19 125.00  30.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1076700000
_diffrn_orient_matrix_UB_12      -0.1344909000
_diffrn_orient_matrix_UB_13      -0.0331833000
_diffrn_orient_matrix_UB_21      0.0709420000
_diffrn_orient_matrix_UB_22      -0.1452501000
_diffrn_orient_matrix_UB_23      0.0378397000
_diffrn_orient_matrix_UB_31      -0.1593012000
_diffrn_orient_matrix_UB_32      0.0263027000
_diffrn_orient_matrix_UB_33      0.0393040000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5050
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.467
_diffrn_reflns_theta_min         3.663
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_description       irregular
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1042 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(12)
_refine_ls_extinction_coef       0.00058(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0336P)^2^+0.1936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0603
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2656
_reflns_number_total             2721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01462_si_002.cif
_cod_data_source_block           exp_1206
_cod_database_code               4033649
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C11 H14 Cl N5 O3 Se'
_chemical_oxdiff_usercomment     LHJ-III-4-UP
_shelx_estimated_absorpt_t_max   0.476
_shelx_estimated_absorpt_t_min   0.327
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N00B(H00B,H00C)
2.b Ternary CH refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00I(H00I)
2.c Secondary CH2 refined with riding coordinates:
 C00K(H00D,H00E)
2.d Aromatic/amide H refined with riding coordinates:
 C00H(H00H)
2.e Idealised Me refined as rotating group:
 C00L(H00G,H00J,H00K)
2.f Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004), O008(H008)
;
_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 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.801