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_7156161
_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         'C15 H23 I1 N2 O6'
_chemical_formula_sum            'C15 H23 I N2 O6'
_chemical_formula_weight         454.26
_chemical_melting_point          419
_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             2018-01-15
_audit_creation_method           CRYSTALS_ver_14.61_build_6720
_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                   8.55340(10)
_cell_length_b                   13.2093(2)
_cell_length_c                   16.1337(2)
_cell_measurement_reflns_used    29438
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1822.86(4)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_av_sigmaI/netI    0.0433
_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            44993
_diffrn_reflns_theta_full        76.318
_diffrn_reflns_theta_max         76.318
_diffrn_reflns_theta_min         4.326
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    14.095
_exptl_absorpt_correction_T_max  0.24
_exptl_absorpt_correction_T_min  0.08
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
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_refine_diff_density_max         0.60
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_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1617 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.0197(14)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0052
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.0005260
_refine_ls_shift/su_mean         0.0000348
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.56P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0805
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0805
_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                3766
_reflns_number_total             3811
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.58
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0302
_oxford_refine_ls_scale          4.85(7)
_oxford_reflns_number_all        3797
_oxford_structure_analysis_title 6604
_cod_data_source_file            c8ob00187a3.cif
_cod_data_source_block           28
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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_original_formula_sum        'C15 H23 I1 N2 O6'
_cod_database_code               7156161
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  0.023(4)
_oxford_bijvoet_difference       0.0197(14)
_oxford_refined_flack_x          0.026(6)