Synthesis of substituted 1,3-diaryl-6,7-dihydro-1H-indol-4(5H)-ones from 1-aryl-2-arylaminoethanones
Kaladevi, Selvam; Sridhar, Jeyaraman; Abhilashamole, Brahmanandan; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai; RSC Advances  (2014) –; doi:10.1039/C4RA03975K

data_7217292
_publ_section_title
;
 Synthesis of substituted 1,3-diaryl-6,7-dihydro-1H-indol-4(5H)-ones from
 1-aryl-2-arylaminoethanones
;
_journal_name_full               'RSC Advances'
_journal_paper_doi               10.1039/C4RA03975K
_journal_year                    2014
_chemical_formula_moiety         'C20 H16 F N O'
_chemical_formula_sum            'C20 H16 F N O'
_chemical_formula_weight         305.34
_chemical_melting_point          470.15
_chemical_name_common
1-(4-Fluoro-phenyl)-3-phenyl-1,5,6,7-tedrahydro-indol-4-one
_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
_audit_creation_date             2013-11-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.488(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.984(2)
_cell_length_b                   12.777(3)
_cell_length_c                   11.583(3)
_cell_measurement_reflns_used    5434
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.404
_cell_measurement_theta_min      2.494
_cell_volume                     1490.9(6)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15645
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         2.022
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0742 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8737.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.428
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0520P)^2^+0.4012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2888
_reflns_number_total             3415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra03975k2.cif
_cod_data_source_block           m6dk
_cod_original_cell_volume        1490.9(5)
_cod_database_code               7217292
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.952
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_shelx_res_checksum              80246