Enantioselective Dearomative [3+2] Cycloaddition of 2-Nitrobenzofurans with Aldehyde-Derived Morita−Baylis−Hillman Carbonates
Guo, Hai-Ming; Yang, Xin-He; Li, Jianping; Wang, Dong-Chao; Xie, Ming-Sheng; Qu, Gui-Rong; Chemical Communications  (2019) –; doi:10.1039/C9CC04542B

data_7123783
_publ_section_title
;
 Enantioselective Dearomative [3+2] Cycloaddition of 2-Nitrobenzofurans
 with Aldehyde-Derived Morita&#x2212;Baylis&#x2212;Hillman Carbonates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04542B
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_compound_source        Synthesis
_chemical_formula_moiety
'C23 H29 N3 O7, 0.25(C3 H6 O), 0.75(C H2 Cl2)'
_chemical_formula_sum            'C24.5 H32 Cl1.5 N3 O7.25'
_chemical_formula_weight         537.70
_chemical_melting_point          379.6(15)
_chemical_name_systematic
'tert-Butyl (5aS,10bS,11aS)-6-acetyl-11a-hydroperoxy-3,3,10b-trimethyl-1,4-dioxo-1,3,4,5a,6,10b,11,11a-octahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-2-carboxylate (16)'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-05 deposited with the CCDC.    2019-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                108.424(2)
_cell_angle_beta                 107.555(2)
_cell_angle_gamma                90.707(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3479(5)
_cell_length_b                   13.3110(7)
_cell_length_c                   13.7777(7)
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.419
_cell_measurement_theta_min      3.111
_cell_volume                     1375.00(13)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       'Bruker APEX3 v2016.1-0'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CMOS area detector'
_diffrn_measurement_device_type  'Bruker D8QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54643
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.478
_diffrn_reflns_theta_min         3.111
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             567
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 3381 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     893
_refine_ls_number_reflns         9648
_refine_ls_number_restraints     640
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0745
_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^)+(0.0846P)^2^+1.9531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.1899
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                8510
_reflns_number_total             9648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04542b2.cif
_cod_data_source_block           7062
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '378.15-381.15' was changed to
'379.6(15)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_formula_sum        'C24.50 H32 Cl1.50 N3 O7.25'
_cod_database_code               7123783
_shelx_shelxl_version_number     2017/1