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_7158998
_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         'C32 H24 Br N'
_chemical_formula_sum            'C32 H24 Br N'
_chemical_formula_weight         502.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-09-26 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.361(2)
_cell_angle_beta                 92.618(1)
_cell_angle_gamma                109.065(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1848(2)
_cell_length_b                   9.7094(2)
_cell_length_c                   14.2815(2)
_cell_measurement_reflns_used    12747
_cell_measurement_temperature    299.5
_cell_measurement_theta_max      24.6170
_cell_measurement_theta_min      2.2290
_cell_volume                     1194.55(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.5
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -56.00  36.00   0.50    7.69    --   16.22 -30.00 -30.00  184
  2  \w     18.00  48.00   0.50    7.69    --   16.22 -94.00 -60.00   60
  3  \w    -35.00  11.00   0.50    7.69    --   16.22 -94.00 -60.00   92
  4  \w    -37.00  22.00   0.50    7.69    --  -14.97 -94.00 -30.00  118
  5  \w    -64.00  90.00   0.50    7.69    --   16.22 -13.00  12.00  308
  6  \w    -11.00  85.00   0.50    7.69    --   16.22  61.00  60.00  192
  7  \w    -37.00  22.00   0.50    7.69    --  -14.97 -94.00 120.00  118
  8  \w     10.00  54.00   0.50    7.69    --   16.22-125.00 150.00   88
  9  \w    -37.00  22.00   0.50    7.69    --  -14.97 -94.00  90.00  118
 10  \w    -64.00  90.00   0.50    7.69    --   16.22 -13.00  12.00  308
 11  \w    -37.00  22.00   0.50    7.69    --  -14.97 -94.00-120.00  118
 12  \w      1.00  27.00   0.50    7.69    --   16.22  13.00-175.00   52
 13  \w    -10.00  90.00   0.50    7.69    --   16.22  30.00-150.00  200
 14  \w    -41.00  59.00   0.50    7.69    --  -14.97  30.00 -90.00  200
 15  \w    -69.00 -10.00   0.50    7.69    --  -14.97 125.00-120.00  118
 16  \w    -89.00  65.00   0.50    7.69    --  -14.97  13.00-175.00  308
 17  \w    -85.00  13.00   0.50    7.69    --  -14.97 -61.00   0.00  196
 18  \w    -95.00  59.00   0.50    7.69    --  -14.97 -13.00  12.00  308
 19  \w    -69.00 -10.00   0.50    7.69    --  -14.97 125.00 120.00  118
 20  \w    -69.00 -10.00   0.50    7.69    --  -14.97 125.00 150.00  118
 21  \w    -85.00  10.00   0.50    7.69    --  -14.97 -45.00-120.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0815881000
_diffrn_orient_matrix_UB_12      -0.0300213000
_diffrn_orient_matrix_UB_13      -0.0004301000
_diffrn_orient_matrix_UB_21      -0.0040793000
_diffrn_orient_matrix_UB_22      0.0715970000
_diffrn_orient_matrix_UB_23      0.0095894000
_diffrn_orient_matrix_UB_31      -0.0068449000
_diffrn_orient_matrix_UB_32      0.0051426000
_diffrn_orient_matrix_UB_33      -0.0491190000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28272
_diffrn_reflns_theta_full        25.0273
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3968
_exptl_crystal_description       block
_exptl_crystal_F_000             515.6167
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.3856
_refine_diff_density_min         -0.4829
_refine_diff_density_rms         0.0723
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             9.1162
_refine_ls_goodness_of_fit_ref   1.0381
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0381
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.0020
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.4775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3396
_reflns_number_total             4208
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ob01873j2.cif
_cod_data_source_block           RB61
_cod_database_code               7158998
_chemical_oxdiff_formula         'C H N O Br'
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C1(H1), C8(H8), C7(H7), C17(H17), C31(H31), C22(H22), C10(H10),
 C30(H30), C27(H27), C18(H18), C14(H14), C20(H20), C28(H28), C29(H29), C12(H12),
  C19(H19), C13(H13), C11(H11)
2.c Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.726