Diastereoselective Synthesis of C2'-Fluorinated Nucleoside Analogues Using an Acyclic Approach.
Dostie, Starr; Prévost, Michel; Mochirian, Philippe; Tanveer, Kashif; Andrella, Nicholas; Rostami, Ariana; Tambutet, Guillaume; Guindon, Yvan; The Journal of organic chemistry 81 (2016) 10769–10790; doi:10.1021/acs.joc.6b01845

data_4037254
_publ_section_title
;
 Diastereoselective Synthesis of C2'-Fluorinated Nucleoside Analogues
 Using an Acyclic Approach.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10769
_journal_page_last               10790
_journal_paper_doi               10.1021/acs.joc.6b01845
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H17 F N2 O4 S, 0.125(C H4 O)'
_chemical_formula_sum            'C12.125 H17.5 F N2 O2.125 S'
_chemical_formula_weight         308.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.3690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8937(3)
_cell_length_b                   14.4166(4)
_cell_length_c                   16.4236(4)
_cell_measurement_reflns_used    9606
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.687
_cell_measurement_theta_min      4.205
_cell_volume                     2803.75(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            97530
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.722
_diffrn_reflns_theta_min         2.351
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    1.510
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1263 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.8271.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1298
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 5719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     757
_refine_ls_number_reflns         12729
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.7405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                12455
_reflns_number_total             12729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01845_si_001.cif
_cod_data_source_block           guin82
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         1233.36
_cod_original_formula_moiety         '4(C12 H17 F N2 O4 S), 0.5(C H4 O)'
_cod_original_formula_units_Z            2
_cod_original_formula_sum        'C48.50 H70 F4 N8 O16.50 S4'
_cod_database_code               4037254
_shelx_estimated_absorpt_t_max   0.852
_shelx_estimated_absorpt_t_min   0.644
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: O81(0.5) H81(0.5) C81(0.5) H81A(0.5) H81B(0.5) H81C(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2B), C6(H6), C21(H21A), C22(H22B), C26(H26), C41(H41A),
 C42(H42B), C46(H46), C61(H61A), C62(H62B), C66(H66)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C24(H24A,H24B), C27(H27A,H27B), C44(H44A,H44B),
 C47(H47A,H47B), C64(H64A,H64B), C67(H67A,H67B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2A), C11(H11), N22(H22A), C31(H31), N42(H42A), C51(H51), N62(H62A),
 C71(H71)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C12(H12A,H12B,H12C), C25(H25A,H25B,H25C), C32(H32A,H32B,
 H32C), C45(H45A,H45B,H45C), C52(H52A,H52B,H52C), C65(H65A,H65B,H65C), C72(H72A,
 H72B,H72C), C81(H81A,H81B,H81C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O21(H21), O22(H22), O41(H41), O42(H42), O61(H61), O62(H62),
 O81(H81)
;
_shelx_res_checksum              25297
_shelx_hkl_checksum              3131
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'