Phosphine-Catalyzed Stereoselective Dearomatization of 3-NO<sub>2</sub>-Indoles with Allenoates.
Cerveri, Alessandro; Faza, Olalla Nieto; López, Carlos Silva; Grilli, Stefano; Monari, Magda; Bandini, Marco; The Journal of organic chemistry 84 (2019) 6347–6355; doi:10.1021/acs.joc.9b00559

data_4033671
_publ_section_title
;
 Phosphine-Catalyzed Stereoselective Dearomatization of
 3-NO<sub>2</sub>-Indoles with Allenoates.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6347
_journal_page_last               6355
_journal_paper_doi               10.1021/acs.joc.9b00559
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C30 H31 N3 O8'
_chemical_formula_weight         561.58
_space_group_crystal_system      monoclinic
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_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_gamma                90
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_cell_length_c                   21.357(3)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    296(2)
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_cell_measurement_theta_min      2.43
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_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.595
_diffrn_measured_fraction_theta_max 0.634
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
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_diffrn_reflns_Laue_measured_fraction_full 0.595
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_diffrn_reflns_theta_max         26.464
_diffrn_reflns_theta_min         1.685
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
_exptl_crystal_F_000             1184
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_exptl_crystal_size_min          0.20
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_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     384
_refine_ls_number_reflns         3756
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_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0684
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+1.5896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.1851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2671
_reflns_number_total             3756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00559_si_004.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2862.0(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4033671
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              44042
_shelx_hkl_checksum              93269