Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via diastereoselective Ireland-Claisen rearrangements
Stephen G. Davies; Ai M. Fletcher; Paul M. Roberts; James E. Thomson; Charlotte M. Zammit; Chem.Commun. 49 (2013) 7037–; doi:10.1039/c3cc43250e

data_7109567
_publ_section_title
;
 Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via
 diastereoselective Ireland-Claisen rearrangements
;
_journal_name_full               Chem.Commun.
_journal_page_first              7037
_journal_paper_doi               10.1039/c3cc43250e
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H18 B1 F4 N1 O2'
_chemical_formula_sum            'C13 H18 B F4 N O2'
_chemical_formula_weight         307.09
_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
_cell_angle_alpha                90
_cell_angle_beta                 90.531(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5150(2)
_cell_length_b                   7.6423(3)
_cell_length_c                   17.2563(6)
_cell_measurement_reflns_used    2014
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     727.27(5)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_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_temperature      150
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.012
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3004
_diffrn_reflns_theta_full        26.671
_diffrn_reflns_theta_max         76.203
_diffrn_reflns_theta_min         5.126
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983), 545 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2038
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.0001332
_refine_ls_shift/su_mean         0.0000137
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.27P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0921
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0921
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              7
_reflns_limit_k_min              -9
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                1978
_reflns_number_total             2045
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.52
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0362
_oxford_refine_ls_scale          16.0(12)
_oxford_reflns_number_all        2038
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c3cc43250e.txt
_cod_data_source_block           30.HBF4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct' changed to 'direct'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_formula_sum        'C13 H18 B1 F4 N1 O2'
_cod_database_code               7109567
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE N   (  20,X'S) H   ( 203,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 213,X'S) H   ( 212,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;