Ag(I)-Catalyzed Cyclization of o-Alkynylacetophenones Facilitated Through Acetal Formation: Synthesis of C3-Naphthyl Indole Derivatives
Golla, Ramesh; Valmuri , Srivardhan; Balamurugan, Rengarajan; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01873J

data_7158997
_publ_section_title
;
 Ag(I)-Catalyzed Cyclization of o-Alkynylacetophenones Facilitated Through
 Acetal Formation: Synthesis of C3-Naphthyl Indole Derivatives
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01873J
_journal_year                    2022
_chemical_formula_moiety         'C31 H24 N2 O3'
_chemical_formula_sum            'C31 H24 N2 O3'
_chemical_formula_weight         472.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-19
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-08-30 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.585(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.630(4)
_cell_length_b                   9.6103(12)
_cell_length_c                   22.543(3)
_cell_measurement_reflns_used    9775
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.30
_cell_volume                     4986.7(12)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0598
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            76610
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.169
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6328
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       needle
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+4.1831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3602
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01873j2.cif
_cod_data_source_block           rb005a_0m_a
_cod_original_cell_volume        4986.5(11)
_cod_database_code               7158997
_shelx_shelxl_version_number     2018/1
_publ_section_exptl
;
Any special experimental details
;
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
;
_shelx_res_checksum              30176
_olex2_submission_special_instructions 'No special instructions were received'