Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins.
Davies, Stephen G.; Fletcher, Ai M.; Lee, James A.; Roberts, Paul M.; Souleymanou, Myriam Y.; Thomson, James E.; Zammit, Charlotte M.; Organic & biomolecular chemistry 12 (2014) 2702–2728; doi:10.1039/c4ob00274a

data_7153726
_publ_section_title
;
 Diastereoselective Ireland-Claisen rearrangements of substituted allyl
 \b-amino esters: applications in the asymmetric synthesis of
 C(5)-substituted transpentacins.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2702
_journal_page_last               2728
_journal_paper_doi               10.1039/c4ob00274a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C27 H29 N1 O2'
_chemical_formula_sum            'C27 H29 N O2'
_chemical_formula_weight         399.53
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                74.3842(8)
_cell_angle_beta                 68.6115(8)
_cell_angle_gamma                80.1552(12)
_cell_formula_units_Z            2
_cell_length_a                   10.0503(2)
_cell_length_b                   10.9520(2)
_cell_length_c                   11.2054(3)
_cell_measurement_reflns_used    4651
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1102.40(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8403
_diffrn_reflns_theta_full        26.964
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         5.173
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9333
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.0001297
_refine_ls_shift/su_mean         0.0000151
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 15.9 24.2 12.1 3.35 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1090
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1090
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2850
_reflns_number_total             5018
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.03
_oxford_diffrn_Wilson_scale      2.36
_oxford_refine_ls_r_factor_ref   0.0525
_oxford_refine_ls_scale          0.692(2)
_oxford_reflns_number_all        3448
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c4ob00274a2.cif
_cod_data_source_block           16
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_formula_sum        'C27 H29 N1 O2'
_cod_database_code               7153726
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  72,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,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   (  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) 
RIDE C   (  25,X'S) H   ( 251,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   ( 302,X'S) H   ( 301,X'S) H   ( 303,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                                                                             
;