Synthesis of 7-Hydroxy-6,7-dihydro-indole and 6',7'-Dihydro-3,7'-biindole Derivatives from Domino Reactions of Arylglyoxals or Methyl Ketones with Enamines
Lu, Xin-Mou; Cai, Zhong-Jian; Li, Jian; Wang, Shun-Yi; Ji, Shun-Jun; RSC Adv.  (2015) –; doi:10.1039/C5RA09478J

data_7220687
_publ_section_title
;
 Synthesis of 7-Hydroxy-6,7-dihydro-indole and 6',7'-Dihydro-3,7'-biindole
 Derivatives from Domino Reactions of Arylglyoxals or Methyl Ketones with
 Enamines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA09478J
_journal_year                    2015
_chemical_formula_moiety         'C23 H23 N O2'
_chemical_formula_sum            'C23 H23 N O2'
_chemical_formula_weight         345.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-24 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8585(16)
_cell_length_b                   11.222(2)
_cell_length_c                   17.434(3)
_cell_measurement_reflns_used    4373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.1
_cell_volume                     1928.8(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1121
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19152
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(4)
_refine_ls_extinction_coef       0.017(3)
_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   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.0897
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+0.3527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1924
_reflns_number_gt                2205
_reflns_number_total             3526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra09478j2.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1928.7(6)
_cod_database_code               7220687