Highly diastereoselective synthesis of enantioenriched anti-alpha-allyl-beta-fluoroamines
Pyne, Stephen G.; Chervis, Philip; Wangngae, Sirilak; Thaima, Thanaphat; Carroll, Anthony; Willis, Anthony; Pattarawarapan, Mookda; Chemical Communications  (2019) –; doi:10.1039/C9CC02765C

data_7123377
_publ_section_title
;
 Highly diastereoselective synthesis of enantioenriched
 anti-alpha-allyl-beta-fluoroamines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02765C
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_moiety         'C20 H22 F1 N1 O2 S1'
_chemical_formula_sum            'C20 H22 F N O2 S'
_chemical_formula_weight         359.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             18-10-29
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2019-03-21 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.192(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0413(3)
_cell_length_b                   11.5956(3)
_cell_length_c                   10.5319(3)
_cell_measurement_reflns_used    10321
_cell_measurement_temperature    150
_cell_measurement_theta_max      29
_cell_measurement_theta_min      4
_cell_volume                     909.29(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'SuperMova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15813
_diffrn_reflns_theta_full        27.345
_diffrn_reflns_theta_max         29.377
_diffrn_reflns_theta_min         3.514
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details 'Flack (1983), 1986 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4405
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.0005528
_refine_ls_shift/su_mean         0.0001139
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.20P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0735
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0735
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4253
_reflns_number_total             4405
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.27
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0308
_oxford_refine_ls_scale          9.4(2)
_oxford_reflns_number_all        4405
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\pyn1821SNMQ\Tony_pyn1821SNMQ_ At 12: 4 on'
_cod_data_source_file            c9cc02765c2.cif
_cod_data_source_block           pyn1821SNMQ
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               7123377
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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