A concise protocol for the synthesis of 2-alkenylindoles through [4 + 1] annulation of aminobenzyl phosphonium salts with acrylaldehydes
Yang, Jia-Cheng; Liao, Mao-Lin; Li, Ping-Gui; Zou, Liang-Hua; Green Chemistry 26 (2024) 9295–9299; doi:10.1039/D4GC02859G

data_7249109
_publ_section_title
;
 A concise protocol for the synthesis of 2-alkenylindoles through [4 + 1]
 annulation of aminobenzyl phosphonium salts with acrylaldehydes
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              9295
_journal_page_last               9299
_journal_paper_doi               10.1039/D4GC02859G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C20 H15 N'
_chemical_formula_sum            'C20 H15 N'
_chemical_formula_weight         269.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-16 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.229(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0588(7)
_cell_length_b                   10.0682(4)
_cell_length_c                   18.9261(8)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      66.782
_cell_measurement_theta_min      3.263
_cell_volume                     2978.8(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37548
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.438
_diffrn_reflns_theta_min         3.262
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1334 before and 0.0837 after correction. The Ratio of minimum to maximum transmission is 0.7854. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
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_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0633P)^2^+0.2161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3812
_reflns_number_total             5451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc02859g2.cif
_cod_data_source_block           cu_20231024zlh_0m_a_pl_sq
_cod_depositor_comments          'Adding full bibliography for 7249109.cif.'
_cod_database_code               7249109
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.901
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N21(H21), C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), N42(H42),
  C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C32(H32), C33(H33),
 C34(H34), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41)
;
_shelx_res_checksum              62348
_shelx_hkl_checksum              13362
_shelx_fab_checksum              48589
_olex2_submission_special_instructions 'No special instructions were received'