Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine
Zhou, Jing; Bai, Lijuan; Liang, Guojuan; Chen, Yongjie; Gan, Zongjie; Wang, Wu; Zhou, Hui; Yu, Yu; RSC Adv. 7 (2017) 39885–; doi:10.1039/C7RA07317H

data_7228927
_publ_section_title
;
 Organocatalytic asymmetric domino Michael/O-alkylation reaction for the
 construction of succinimide substituted 3(2H)-furanones catalyzed by
 quinine
;
_journal_issue                   63
_journal_name_full               'RSC Adv.'
_journal_page_first              39885
_journal_paper_doi               10.1039/C7RA07317H
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 Br N O5'
_chemical_formula_sum            'C16 H14 Br N O5'
_chemical_formula_weight         380.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-28 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.759(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4013(8)
_cell_length_b                   8.2636(13)
_cell_length_c                   17.057(3)
_cell_measurement_reflns_used    6374
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.93
_cell_measurement_theta_min      2.42
_cell_volume                     752.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7512
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.929
_diffrn_reflns_theta_min         1.208
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          1.250
_exptl_crystal_size_mid          1.000
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   0.7462
_exptl_transmission_factor_min   0.2939
_refine_diff_density_max         1.404
_refine_diff_density_min         -1.570
_refine_diff_density_rms         0.174
_refine_ls_abs_structure_details
;
 Flack x determined using 1509 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.135(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1010P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                3798
_reflns_number_total             4093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra07317h1.cif
_cod_data_source_block           mo_cy_zj1_0m
_cod_original_cell_volume        752.5(2)
_cod_database_code               7228927
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.130
_shelx_estimated_absorpt_t_max   0.699
_shelx_res_checksum              36458