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_1555448
_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         'C15 H12 O3'
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25
_chemical_name_systematic        2,7-dimethoxy-9H-fluoren-9-one
_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'
_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                 93.567(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8593(10)
_cell_length_b                   4.0079(5)
_cell_length_c                   36.679(4)
_cell_measurement_reflns_used    902
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.7360
_cell_measurement_theta_min      3.6185
_cell_volume                     1153.1(2)
_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
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
  1 omega  -71.00  -42.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 29

  2 omega -100.00  -36.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 64

  3 omega  -15.00   13.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -180.0000 28

  4 omega   -1.00   55.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -60.0000 56

  5 omega   54.00   81.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  120.0000 27

  6 omega   31.00   80.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -180.0000 49

  7 omega  -14.00   72.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   30.0000 86

  8 omega   38.00   93.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 55

  9 omega   39.00   88.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 49

 10 omega   58.00   84.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 26

 11 omega   94.00  168.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  150.0000 74

 12 omega   89.00  174.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   90.0000 85

 13 omega   62.00  132.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 70

 14 omega   89.00  167.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   59.0000 -165.0000 78
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1844111000
_diffrn_orient_matrix_UB_12      0.0382044000
_diffrn_orient_matrix_UB_13      -0.0163325000
_diffrn_orient_matrix_UB_21      0.0572542000
_diffrn_orient_matrix_UB_22      0.2880993000
_diffrn_orient_matrix_UB_23      -0.0241989000
_diffrn_orient_matrix_UB_31      0.0376107000
_diffrn_orient_matrix_UB_32      -0.2513771000
_diffrn_orient_matrix_UB_33      -0.0302537000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            3705
_diffrn_reflns_theta_full        70.87
_diffrn_reflns_theta_max         70.87
_diffrn_reflns_theta_min         4.83
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92621
_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    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_preparation       'Synthesized Compound'
_exptl_crystal_recrystallization_method
'Recrystallized from the mixture of dichloromethane and hexane'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.361
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.361
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0849
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+3.9552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2458
_refine_ls_wR_factor_ref         0.2543
_reflns_number_gt                1474
_reflns_number_total             2142
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03077_si_002.cif
_cod_data_source_block           exp_4457
_cod_database_code               1555448
_chemical_oxdiff_formula         'C15 H12 O3'
_reflns_odcompleteness_completeness 98.29
_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:
 C5(H5), C7(H7), C9(H9), C13(H13), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_olex2_date_sample_data_collection 2014-12-10
_olex2_submission_original_sample_id 2,7-dimethoxy-9H-fluoren-9-one
_olex2_submission_special_instructions 'No special instructions were received'