Organocatalytic Asymmetric Allylic Alkylation of Morita-Baylis-Hillman Carbonates with Diethyl 2-Aminomalonate Assisted by In Situ Protection.
Zheng, Yu; Wang, Jing; Xia, Peng-Ju; Zhao, Qing-Lan; Xiao, Jun-An; Xiang, Hao-Yue; Chen, Xiao-Qing; Yang, Hua; The Journal of organic chemistry 82 (2017) 12202–12208; doi:10.1021/acs.joc.7b02064

data_4033096
_publ_section_title
;
 Organocatalytic Asymmetric Allylic Alkylation of Morita-Baylis-Hillman
 Carbonates with Diethyl 2-Aminomalonate Assisted by In Situ Protection.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12202
_journal_page_last               12208
_journal_paper_doi               10.1021/acs.joc.7b02064
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C32 H33 Br N2 O8 S'
_chemical_formula_weight         685.58
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.875(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2219(7)
_cell_length_b                   8.5559(3)
_cell_length_c                   21.5811(8)
_cell_measurement_reflns_used    6768
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.63
_cell_volume                     3364.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19538
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    1.334
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.052(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6768
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.077
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+1.1552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                5509
_reflns_number_total             6768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02064_si_002.cif
_cod_data_source_block           ja
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033096.cif.

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      C2
_cod_original_formula_sum        'C4.27 H4.40 Br0.13 N0.27 O1.07 S0.13'
_cod_original_formula_units_Z    30
_cod_original_formula_weight     91.41
_cod_database_code               4033096