Total Stereoselective Michael Addition of N- and S- Nucleophiles to a d-Erythrosyl 1,5-Lactone Derivative. Experimental and Theoretical Studies Devoted to the Synthesis of 2,6-Dideoxy-4-functionalized-d- ribono-hexono-1,4-lactone.
Rocha, Juliana F.; Freitas, David S.; Noro, Jennifer; Silva Teixeira, Carla S.; Sousa, Cristina E. A.; Alves, Maria J.; Cerqueira, Nuno M. F. S. A.; The Journal of organic chemistry 83 (2018) 8011–8019; doi:10.1021/acs.joc.8b00769

data_4035560
_publ_section_title
;
 Total Stereoselective Michael Addition of N- and S- Nucleophiles to a
 d-Erythrosyl 1,5-Lactone Derivative. Experimental and Theoretical Studies
 Devoted to the Synthesis of 2,6-Dideoxy-4-functionalized-d-
 ribono-hexono-1,4-lactone.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8011
_journal_page_last               8019
_journal_paper_doi               10.1021/acs.joc.8b00769
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H18 N O4, Cl'
_chemical_formula_sum            'C13 H18 Cl N O4'
_chemical_formula_weight         287.73
_chemical_name_common            'DF2 - 17ALE001'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                78.393(2)
_cell_angle_beta                 80.255(2)
_cell_angle_gamma                87.923(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4859(2)
_cell_length_b                   7.6978(2)
_cell_length_c                   16.1908(5)
_cell_measurement_reflns_used    3265
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.2645
_cell_measurement_theta_min      2.6044
_cell_volume                     660.08(4)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 16.6666
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  '\k--geometry diffractometer'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7504
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.30
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'SIEMENS KFN MO 2K-90'
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'TWINABS-2012/1 - Bruker AXS scaling for twinned crystals'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.269
_refine_ls_abs_structure_details
;

Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         7504
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.0276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                6305
_reflns_number_total             7504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00769_si_001.cif
_cod_data_source_block           17ALE001
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4035560
_shelx_res_checksum              12459
_shelx_hkl_checksum              36669