Synthesis of Indole-Substituted Indanones via Palladium(II)-Catalyzed Tandem Reaction of ortho-Electron-Deficient Alkynyl-Substituted Aryl Aldehydes with Indoles.
Zhang, Jianbo; Han, Xiuling; Lu, Xiyan; Organic letters 18 (2016) 2898–2901; doi:10.1021/acs.orglett.6b01240

data_1543828
_publ_section_title
;
 Synthesis of Indole-Substituted Indanones via Palladium(II)-Catalyzed
 Tandem Reaction of ortho-Electron-Deficient Alkynyl-Substituted Aryl
 Aldehydes with Indoles.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2898
_journal_page_last               2901
_journal_paper_doi               10.1021/acs.orglett.6b01240
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H22 N2 O2'
_chemical_formula_sum            'C26 H22 N2 O2'
_chemical_formula_weight         394.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.3078(13)
_cell_length_b                   10.3786(7)
_cell_length_c                   20.7335(14)
_cell_measurement_reflns_used    5966
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.136
_cell_measurement_theta_min      2.23
_cell_volume                     4154.7(5)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32803
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         1.962
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0631 before and 0.0466 after correction.
The Ratio of minimum to maximum transmission is 0.9160.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_coef       0.0038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         9558
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0448P)^2^+0.4252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6231
_reflns_number_total             9558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01240_si_002.cif
_cod_data_source_block           dm14756
_cod_database_code               1543828
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C18(H18), C36(H36), C44(H44)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C31(H31), C34(H34), C38(H38), C39(H39), C40(H40), C41(H41),
 C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C20(H20A,H20B,H20C), C35(H35A,H35B,H35C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              33402
_shelx_hkl_checksum              29470
_olex2_submission_special_instructions 'No special instructions were received'