Diastereoselective reduction of the tricarbonyl moiety in bicyclic tetramates giving pyroglutamates.
Josa-Culleré, Laia; Christensen, Kirsten E.; Moloney, Mark G.; Organic & biomolecular chemistry 16 (2018) 2705–2710; doi:10.1039/c8ob00187a

data_7156160
_publ_section_title
;
 Diastereoselective reduction of the tricarbonyl moiety in bicyclic
 tetramates giving pyroglutamates.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2705
_journal_page_last               2710
_journal_paper_doi               10.1039/c8ob00187a
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H26 N2 O7'
_chemical_formula_sum            'C16 H26 N2 O7'
_chemical_formula_weight         358.39
_chemical_melting_point          ?
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2016-07-28
_audit_creation_method           CRYSTALS_ver_14.43
_audit_update_record
;
2018-01-16 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5004(2)
_cell_length_b                   12.8701(2)
_cell_length_c                   16.4218(3)
_cell_measurement_reflns_used    12446
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1796.56(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     1.54184
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22249
_diffrn_reflns_theta_full        76.168
_diffrn_reflns_theta_max         76.168
_diffrn_reflns_theta_min         4.365
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.875
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768.000
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983), 1597 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.0004836
_refine_ls_shift/su_mean         0.0000415
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.19P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0958
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0958
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3660
_reflns_number_total             3754
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.38
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0362
_oxford_refine_ls_scale          7.9(2)
_oxford_reflns_number_all        3739
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6603
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, FIRST(U'S) UNTIL C(24) 
CONT O(113,U[ISO]) UNTIL C(114) 
CONT ENANTIO 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   4,X'S) H   (  42,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) H   ( 123,X'S) 
RIDE C   (  14,X'S) H   ( 143,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 163,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 203,X'S) H   ( 202,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 223,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE C   ( 114,X'S) H   (1142,X'S) H   (1141,X'S) H   (1143,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
SAME N(11)  O(13)  C(14) AND 
CONT N(11)  O(113)  C(114) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = N(11) TO O(13) 
VIBR .0, 0.00500 = C(12) TO C(9) 
VIBR .0, 0.00500 = O(13) TO C(9) 
VIBR .0, 0.00500 = O(13) TO C(12) 
VIBR .0, 0.00200 = N(11) TO C(12) 
VIBR .0, 0.00200 = N(11) TO O(113) 
VIBR .0, 0.00500 = O(113) TO C(9) 
VIBR .0, 0.00500 = O(113) TO C(12) 
VIBR .0, 0.00200 = O(13) TO C(14) 
VIBR .0, 0.00500 = C(14) TO N(11) 
VIBR .0, 0.00200 = O(113) TO C(114) 
VIBR .0, 0.00500 = C(114) TO N(11) 
U(IJ) .0, 0.04000 = N(11) TO O(13) 
U(IJ) .0, 0.04000 = N(11) TO O(113) 
U(IJ) .0, 0.08000 = O(13) TO C(14) 
U(IJ) .0, 0.08000 = O(113) TO C(114) 
END                                                                             
;
_cod_data_source_file            c8ob00187a3.cif
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/home/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.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156160--7156161.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               7156160