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_7109565
_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         'C31 H35 N1 O2'
_chemical_formula_sum            'C31 H35 N O2'
_chemical_formula_weight         453.62
_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                 111.582(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9925(2)
_cell_length_b                   16.7779(4)
_cell_length_c                   10.6442(3)
_cell_measurement_reflns_used    7162
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     1327.29(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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_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  0.022
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13581
_diffrn_reflns_theta_full        74.704
_diffrn_reflns_theta_max         77.015
_diffrn_reflns_theta_min         4.467
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  0.97
_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    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 1792 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4635
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.0003694
_refine_ls_shift/su_mean         0.0000394
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.19P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0833
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0833
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              20
_reflns_limit_k_min              -15
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                4412
_reflns_number_total             4653
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.05
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0343
_oxford_refine_ls_scale          8.7(2)
_oxford_reflns_number_all        4635
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c3cc43250e.txt
_cod_data_source_block           20
_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        'C31 H35 N1 O2'
_cod_database_code               7109565
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,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) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 141,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) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 233,X'S) H   ( 232,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 333,X'S) H   ( 332,X'S) 
RIDE C   (  34,X'S) H   ( 342,X'S) H   ( 341,X'S) H   ( 343,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                                                                             
;