A Domino Palladium-Catalyzed Cyclization: One-pot Synthesis of 4b-Alkyl-10-phenyl-4b,5-dihydroindeno[2,1-a]indenes via Carbopalladation Followed by C-H Activation.
Ramesh, Karu; Satyanarayana, Gedu; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00254

data_4032436
_publ_section_title
;
 A Domino Palladium-Catalyzed Cyclization: One-pot Synthesis of
 4b-Alkyl-10-phenyl-4b,5-dihydroindeno[2,1-a]indenes via Carbopalladation
 Followed by C-H Activation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00254
_journal_year                    2017
_chemical_formula_moiety         'C25 H22'
_chemical_formula_sum            'C25 H22'
_chemical_formula_weight         322.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-01
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.719(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4038(5)
_cell_length_b                   9.7159(6)
_cell_length_c                   22.1773(15)
_cell_measurement_reflns_used    1013
_cell_measurement_temperature    323
_cell_measurement_theta_max      66.9580
_cell_measurement_theta_min      4.9320
_cell_volume                     1810.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      323
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.2
_diffrn_measured_fraction_theta_max 0.7978
_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     12.00  51.00   1.00    1.50    --    0.00  57.00-180.00   39
  2  \w    -30.00  29.00   1.00    3.18    --  -42.50  38.00-150.00   59
  3  \w    -42.00  16.00   1.00    3.18    --  -42.50  25.00   0.00   58
  4  \w    -29.00  20.00   1.00    3.18    --  -42.50  38.00 120.00   49
  5  \w     49.00  84.00   1.00    3.18    --  109.95 -25.00-120.00   35
  6  \w     39.00  79.00   1.00    3.18    --  109.95 -38.00 -30.00   40
  7  \w     44.00  72.00   1.00    3.18    --  109.95 -25.00  60.00   28
  8  \w    100.00 161.00   1.00    3.18    --  109.95 111.00 -60.00   61
  9  \w     38.00  86.00   1.00    3.18    --  109.95 -38.00-180.00   48
 10  \w     62.00  91.00   1.00    3.18    --  109.95 -38.00 120.00   29
 11  \w     55.00  92.00   1.00    3.18    --  109.95 -38.00   0.00   37
 12  \w     56.00  93.00   1.00    3.18    --  109.95 -38.00 -90.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0785789000
_diffrn_orient_matrix_UB_12      -0.0996017000
_diffrn_orient_matrix_UB_13      0.0453951000
_diffrn_orient_matrix_UB_21      0.1585458000
_diffrn_orient_matrix_UB_22      0.0124957000
_diffrn_orient_matrix_UB_23      -0.0336436000
_diffrn_orient_matrix_UB_31      0.0478446000
_diffrn_orient_matrix_UB_32      0.1228465000
_diffrn_orient_matrix_UB_33      0.0403753000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3800
_diffrn_reflns_theta_full        71.42
_diffrn_reflns_theta_max         71.42
_diffrn_reflns_theta_min         4.97
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0605
_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^)+(0.0897P)^2^+0.0466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1793
_reflns_number_gt                1930
_reflns_number_total             2842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00254_si_002.cif
_cod_data_source_block           exp_4967
_cod_database_code               4032436
_chemical_oxdiff_formula         'C24 H25'
_reflns_odcompleteness_completeness 82.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.857