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_7109566
_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         'C16 H20 Cl3 F2 N1 O4'
_chemical_formula_sum            'C16 H20 Cl3 F2 N O4'
_chemical_formula_weight         434.69
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 110.830(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.0016(5)
_cell_length_b                   6.69150(10)
_cell_length_c                   12.9605(2)
_cell_measurement_reflns_used    13241
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     2026.55(7)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.023
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19694
_diffrn_reflns_theta_full        76.104
_diffrn_reflns_theta_max         76.104
_diffrn_reflns_theta_min         3.649
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.452
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_correction_T_min  0.27
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896.000
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.44
_refine_ls_abs_structure_details 'Flack (1983), 1910 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.005(11)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.0046285
_refine_ls_shift/su_mean         0.0002582
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.14P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0822
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0822
_reflns_limit_h_max              29
_reflns_limit_h_min              -31
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4120
_reflns_number_total             4226
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.94
_oxford_diffrn_Wilson_scale      0.11
_oxford_refine_ls_r_factor_ref   0.0326
_oxford_refine_ls_scale          3.38(3)
_oxford_reflns_number_all        4207
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c3cc43250e.txt
_cod_data_source_block           29.C7H4F2O2.CHCl3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
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_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C16 H20 Cl3 F2 N1 O4'
_cod_database_code               7109566
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
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) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE N   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) H   ( 263,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) H   ( 273,X'S) 
RIDE C   (  28,X'S) H   ( 283,X'S) H   ( 282,X'S) H   ( 281,X'S) 
EQUIV PART (1001,OCC) PART (1002, OCC) 
WEIGHT -1 PART (1002,OCC) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;