Base-controlled dearomative [3+2] cycloadditions between 3-nitro-indoles and fumaric acid amide esters
Tian, Heng-Zhi; Wu, Sheng-Feng; Zhuang, Guo-Wei; Lin, Guo-Qiang; Sun, Xing-Wen; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00296E

data_7158587
_publ_section_title
;
 Base-controlled dearomative [3+2] cycloadditions between 3-nitro-indoles
 and fumaric acid amide esters
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00296E
_journal_year                    2022
_chemical_formula_sum            'C23 H22 N2 O6 S'
_chemical_formula_weight         454.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-06-07 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                105.673(13)
_cell_angle_beta                 95.539(11)
_cell_angle_gamma                102.695(12)
_cell_formula_units_Z            2
_cell_length_a                   9.9808(13)
_cell_length_b                   10.3586(15)
_cell_length_c                   11.4372(19)
_cell_measurement_reflns_used    8223
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      60.56
_cell_measurement_theta_min      3.54
_cell_volume                     1095.3(3)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14316
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.667
_diffrn_reflns_theta_min         3.541
_exptl_absorpt_coefficient_mu    1.096
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5009
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0714P)^2^+0.1407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4285
_reflns_number_total             5009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00296e2.cif
_cod_data_source_block           ga_80504a_a
_cod_database_code               7158587
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.764
_shelx_estimated_absorpt_t_max   0.862
_shelx_res_checksum              90984