Highly stereoselective synthesis of 2,3-dihydrofurans via cascade Michael addition-alkylation process: nitro group as the leaving group
Mo, Yiran; Liu, Siyang; Liu, Yingying; Ye, Ling; Shi, Zhichuan; Zhao, Zhi-Gang; Li, Xuefeng; Chemical Communications  (2019) –; doi:10.1039/C9CC01509D

data_7123411
_publ_section_title
;
 Highly stereoselective synthesis of 2,3-dihydrofurans via cascade Michael
 addition-alkylation process: nitro group as the leaving group
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01509D
_journal_year                    2019
_chemical_formula_sum            'C19 H13 N O3'
_chemical_formula_weight         303.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-04-11 deposited with the CCDC.    2019-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.814(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6309(5)
_cell_length_b                   20.4650(11)
_cell_length_c                   8.3752(4)
_cell_measurement_reflns_used    6011
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.61
_cell_volume                     1474.10(14)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0875
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20225
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_min         2.636
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc/petroleum ether'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0686P)^2^+0.5805P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2439
_reflns_number_total             3807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01509d2.cif
_cod_data_source_block           mo_d1_0ma
_cod_database_code               7123411
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              71860