Phosphine-catalyzed regiospecific (3 + 2) cyclization of 3-nitroindoles with allene esters.
Jin, Li-Wen; Jiang, Fei; Chen, Ke-Wei; Du, Bai-Xiang; Mei, Guang-Jian; Shi, Feng; Organic & biomolecular chemistry 17 (2019) 3894–3901; doi:10.1039/c9ob00432g

data_7156741
_publ_section_title
;
 Phosphine-catalyzed regiospecific (3 + 2) cyclization of 3-nitroindoles
 with allene esters.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3894
_journal_page_last               3901
_journal_paper_doi               10.1039/c9ob00432g
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C21 H18 N2 O5'
_chemical_formula_sum            'C21 H18 N2 O5'
_chemical_formula_weight         378.37
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2019-02-20 deposited with the CCDC.    2019-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.560(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7507(18)
_cell_length_b                   9.3997(11)
_cell_length_c                   12.8142(15)
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.16
_cell_measurement_theta_min      2.52
_cell_volume                     1893.5(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.950
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11052
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.074
_diffrn_reflns_theta_min         2.525
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0515 before and 0.0405 after correction. The Ratio of minimum to maximum transmission is 0.8933. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4370
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0715
_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^)+(0.1417P)^2^+0.3207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2573
_reflns_number_total             4370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00432g2.cif
_cod_data_source_block           sf20180411-2
_cod_depositor_comments          'Adding full bibliography for 7156741.cif.'
_cod_database_code               7156741
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-C20
 1.53 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
O3 \\sim C20 \\sim C21: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C20(H20A,H20B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              69714
_olex2_submission_special_instructions 'No special instructions were received'