Asymmetric synthesis of highly functionalized furanones via direct Michael reactions mediated by a bulky primary amine
Huang, Huicai; Lu, Xue; Mao, Yukang; Ye, Jinxing; Organic Chemistry Frontiers 6 (2019) 1080–; doi:10.1039/C8QO01132J

data_1554513
_publ_section_title
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 Asymmetric synthesis of highly functionalized furanones via direct
 Michael reactions mediated by a bulky primary amine
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1080
_journal_paper_doi               10.1039/C8QO01132J
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H19 Br O3'
_chemical_formula_weight         399.27
_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_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-05-10 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.687(8)
_cell_length_b                   12.035(9)
_cell_length_c                   14.902(11)
_cell_measurement_reflns_used    1994
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.258
_cell_measurement_theta_min      5.087
_cell_volume                     1917(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0833
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9193
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    2.160
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0895
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.560
_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   -0.006(13)
_refine_ls_extinction_coef       0.042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                2315
_reflns_number_total             3560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo01132j2.cif
_cod_data_source_block           cd212166
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1554513