Organocatalytic Doubly Annulative Approach to 3,4-Dihydrocoumarins Bearing a Fused Pyrrolidine Scaffold.
Kowalczyk, Dorota; Albrecht, Łukasz; The Journal of organic chemistry 81 (2016) 6800–6807; doi:10.1021/acs.joc.6b00975

data_4036924
_publ_section_title
;
 Organocatalytic Doubly Annulative Approach to 3,4-Dihydrocoumarins
 Bearing a Fused Pyrrolidine Scaffold.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6800
_journal_page_last               6807
_journal_paper_doi               10.1021/acs.joc.6b00975
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H24 N2 O9'
_chemical_formula_weight         484.45
_chemical_name_systematic
;
(3R,3aS,9bR)-diethyl 3-(2-methoxyphenyl)-8-nitro-4-oxo-1,3a,4,9b-
tetrahydrochromeno[4,3-b]pyrrole-2,2(3H)-dicarboxylate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.78800(10)
_cell_length_b                   13.1767(3)
_cell_length_c                   25.9973(5)
_cell_measurement_reflns_used    9590
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      150.001
_cell_measurement_theta_min      6.800
_cell_volume                     2325.29(8)
_computing_cell_refinement       'APEX2-2015 (Bruker, 2015)'
_computing_data_collection       'APEX2-2015 (Bruker, 2015)'
_computing_data_reduction        'APEX2-2015 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         75.044
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'sealed X-ray microsource'
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.6601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2016 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0378P)^2^+0.6214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0734
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4786
_reflns_number_total             4787
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00975_si_002.cif
_cod_data_source_block           1
_cod_database_code               4036924
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              51354
_shelx_hkl_checksum              97860