Synthesis of (2S)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination.
De Schutter, Coralie; Sari, Ozkan; Coats, Steven J.; Amblard, Franck; Schinazi, Raymond F.; The Journal of organic chemistry 82 (2017) 13171–13178; doi:10.1021/acs.joc.7b02245

data_4033243
_publ_section_title
;
 Synthesis of (2S)-2-Chloro-2-fluororibolactone via Stereoselective
 Electrophilic Fluorination.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13171
_journal_page_last               13178
_journal_paper_doi               10.1021/acs.joc.7b02245
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H35 Cl O4 Si2'
_chemical_formula_sum            'C17 H35 Cl O4 Si2'
_chemical_formula_weight         395.08
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-13
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.555(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0970(3)
_cell_length_b                   25.7082(11)
_cell_length_c                   7.4230(3)
_cell_measurement_reflns_used    14891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.5490
_cell_measurement_theta_min      2.9150
_cell_volume                     1089.43(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 HyPix
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     47.00  73.00   0.50    7.00    --   25.02  38.00  30.00   52
  2  \w     27.00  98.00   0.50    7.00    --   25.02  77.00 -60.00  142
  3  \w     39.00  65.00   0.50    7.00    --   25.02 178.00-150.00   52
  4  \w     15.00  57.00   0.50    7.00    --   25.02  77.00-120.00   84
  5  \w     10.00  98.00   0.50    7.00    --   25.02  57.00-120.00  176
  6  \w     63.00  90.00   0.50    7.00    --   25.02 178.00 120.00   54
  7  \w    -37.00  46.00   0.50    7.00    --  -25.02  38.00-180.00  166
  8  \w    -30.00  39.00   0.50    7.00    --   25.02 -57.00-180.00  138
  9  \w      7.00  58.00   0.50    7.00    --   25.02 -99.00-120.00  102
 10  \w      3.00  59.00   0.50    7.00    --   25.02 -99.00 -60.00  112
 11  \w    -25.00  26.00   0.50    7.00    --   25.02 -99.00  30.00  102
 12  \w      2.00  57.00   0.50    7.00    --   25.02-113.00 172.00  110
 13  \w    -95.00 -11.00   0.50    7.00    --  -25.02 -57.00 -30.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0499542000
_diffrn_orient_matrix_UB_12      -0.0209980000
_diffrn_orient_matrix_UB_13      0.0340974000
_diffrn_orient_matrix_UB_21      0.0279320000
_diffrn_orient_matrix_UB_22      -0.0171145000
_diffrn_orient_matrix_UB_23      -0.0637597000
_diffrn_orient_matrix_UB_31      0.1103502000
_diffrn_orient_matrix_UB_32      -0.0052017000
_diffrn_orient_matrix_UB_33      0.0720167000
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30346
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.313
_diffrn_reflns_theta_min         2.931
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.362
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of hexane and DCM by slow evaporation'
_exptl_crystal_size_max          0.671
_exptl_crystal_size_mid          0.427
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 4176 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         10546
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0595P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.963
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                9642
_reflns_number_total             10546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02245_si_002.cif
_cod_data_source_block           cdesch01
_cod_depositor_comments
'Adding full bibliography for 4033242--4033243.cif.'
_cod_database_code               4033243
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C34 H70 Cl2 O8 Si4'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.823
_diffrn_oxdiff_ac3_digest_frames
;
01b1837f1d9f8d6f8382dae998f313d5f601458c618
;
_diffrn_oxdiff_ac3_digest_hkl
;
011c3438d7750044c1fe626385ba14cafcdbb2
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 C7B(H7BA,H7BB,H7BC), C7(H7A,H7B,H7C), C6B(H6BA,H6BB,H6BC), C11B(H11A,H11B,
 H11C), C11(H11D,H11E,H11F), C6(H6A,H6B,H6C), C10B(H10A,H10B,H10C), C9B(H9BA,
 H9BB,H9BC), C10(H10D,H10E,H10F), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              42670
_shelx_hkl_checksum              67901
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_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 1.656
_oxdiff_exptl_absorpt_empirical_full_min 0.524