Domino Oxidative [Pd]-Catalysis: One-Pot Synthesis of Fluorenones Starting from Simple Benzylamines and Iodo Arenes.
Ravi Kumar, Devarapalli; Satyanarayana, Gedu; Organic letters 17 (2015) 5894–5897; doi:10.1021/acs.orglett.5b03077

data_1555447
_publ_section_title
;
 Domino Oxidative [Pd]-Catalysis: One-Pot Synthesis of Fluorenones
 Starting from Simple Benzylamines and Iodo Arenes.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5894
_journal_page_last               5897
_journal_paper_doi               10.1021/acs.orglett.5b03077
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_weight         316.35
_chemical_name_systematic        7-methoxy-1-(4-methoxyphenyl)-9H-fluoren-9-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.1080(7)
_cell_length_b                   7.5400(5)
_cell_length_c                   27.9119(14)
_cell_measurement_reflns_used    2734
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9100
_cell_measurement_theta_min      2.9250
_cell_volume                     3179.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega   21.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 38

  2 omega  -80.00  -41.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  125.0000  -30.0000 39

  3 omega    2.00   33.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  120.0000 31

  4 omega  -52.00   -4.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  120.0000 48

  5 omega   81.00  108.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -       54.0000  173.0000  -55.0000 27

  6 omega    4.00   93.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -150.0000 89

  7 omega   46.00   76.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -60.0000 30

  8 omega   50.00   76.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 26

  9 omega  103.00  174.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   86.0000 -144.0000 71

 10 omega   45.00   96.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 51

 11 omega   36.00   83.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 47

 12 omega   67.00   92.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 25

 13 omega   39.00  135.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -180.0000 96

 14 omega  -69.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -120.0000 98

 15 omega -101.00  -28.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000 -120.0000 73

 16 omega   35.00  122.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 87

 17 omega   32.00  125.00   1.0000    4.6200
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  150.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0832848000
_diffrn_orient_matrix_UB_12      -0.0978934000
_diffrn_orient_matrix_UB_13      0.0181017000
_diffrn_orient_matrix_UB_21      0.0370246000
_diffrn_orient_matrix_UB_22      -0.1766605000
_diffrn_orient_matrix_UB_23      -0.0193488000
_diffrn_orient_matrix_UB_31      0.0456927000
_diffrn_orient_matrix_UB_32      -0.0340085000
_diffrn_orient_matrix_UB_33      0.0484658000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10791
_diffrn_reflns_theta_full        70.88
_diffrn_reflns_theta_max         70.88
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'yellowish yellow'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1265
_exptl_crystal_preparation       'Synthesized compound'
_exptl_crystal_recrystallization_method
'Recrystallyzed from the mixture of dichloromethane and hexane'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1044P)^2^+0.2728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1986
_reflns_number_gt                2171
_reflns_number_total             3001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03077_si_001.cif
_cod_data_source_block           Aryl-fluorenone
_cod_database_code               1555447
_chemical_oxdiff_formula         'C14 H16 N O'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C19(H19), C11(H11), C6(H6), C15(H15), C16(H16), C9(H9),
 C10(H10), C5(H5)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_olex2_date_sample_data_collection 2014-06-09
_olex2_submission_special_instructions 'No special instructions were received'