Monodentate Transient Directing Group Assisted Pd-Catalyzed Direct Dehydrogenative Cross-Coupling of Benzaldehydes with Arenes toward 9-Fluorenones.
Wang, Yi-Feng; Xu, Wen-Gang; Sun, Bing; Yu, Qin-Qin; Li, Tuan-Jie; Zhang, Fang-Lin; The Journal of organic chemistry 84 (2019) 13104–13111; doi:10.1021/acs.joc.9b02139

data_4034101
_publ_section_title
;
 Monodentate Transient Directing Group Assisted Pd-Catalyzed Direct
 Dehydrogenative Cross-Coupling of Benzaldehydes with Arenes toward
 9-Fluorenones.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13104
_journal_page_last               13111
_journal_paper_doi               10.1021/acs.joc.9b02139
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H9 Br O'
_chemical_formula_sum            'C14 H9 Br O'
_chemical_formula_weight         273.12
_chemical_name_systematic        1
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.626(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6739(2)
_cell_length_b                   3.95380(10)
_cell_length_c                   36.2385(10)
_cell_measurement_reflns_used    2680
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9510
_cell_measurement_theta_min      2.4540
_cell_volume                     1098.36(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     84.00 121.00   0.50    0.09    --   43.18 178.00  90.00   74
  2  \w    -95.00 -70.00   0.50    0.50    --  -90.25 125.00  30.00   50
  3  \w     36.00  97.00   0.50    0.50    --  109.88 -94.00-150.00  122
  4  \w     61.00 104.00   0.50    0.50    --  109.88 -94.00 -60.00   86
  5  \w     93.00 118.00   0.50    0.50    --  109.88-125.00 -30.00   50
  6  \w     32.00  83.00   0.50    0.50    --  109.88 -30.00  30.00  102
  7  \w     41.00  67.00   0.50    0.50    --  109.88 -61.00 -60.00   52
  8  \w     91.00 133.00   0.50    0.50    --  109.88 -30.00  30.00   84
  9  \w     76.00 128.00   0.50    0.50    --  109.88 -61.00 -60.00  104
 10  \w     31.00 135.00   0.50    0.50    --  109.88 -27.00-171.00  208
 11  \w   -122.00 -18.00   0.50    0.09    --  -43.18 -27.00-171.00  208
 12  \w    -96.00 -70.00   0.50    0.50    --  -90.25 -27.00-171.00   52
 13  \w   -128.00-100.00   0.50    0.50    --  -90.25 -27.00-171.00   56
 14  \w    -98.00 -73.00   0.50    0.50    --  -90.25  27.00  -9.00   50
 15  \w   -110.00 -50.00   0.50    0.50    --  -90.25  30.00-150.00  120
 16  \w    -36.00 -10.00   0.50    0.09    --  -43.18  27.00  -9.00   52
 17  \w     -4.00  36.00   0.50    0.09    --  -43.18  27.00  -9.00   80
 18  \w    -37.00 -12.00   0.50    0.50    --  -90.25  30.00-150.00   50
 19  \w     66.00  94.00   0.50    0.09    --   43.18  27.00  -9.00   56
 20  \w    117.00 177.00   0.50    0.50    --  109.88  27.00  -9.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1671887000
_diffrn_orient_matrix_UB_12      0.0015781000
_diffrn_orient_matrix_UB_13      0.0252110000
_diffrn_orient_matrix_UB_21      0.1042333000
_diffrn_orient_matrix_UB_22      0.1361031000
_diffrn_orient_matrix_UB_23      -0.0321553000
_diffrn_orient_matrix_UB_31      -0.0397321000
_diffrn_orient_matrix_UB_32      0.3650511000
_diffrn_orient_matrix_UB_33      0.0118913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            5229
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         2.44
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0855P)^2^+0.6712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                1731
_reflns_number_total             1956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02139_si_002.cif
_cod_data_source_block           exp_2648
_cod_database_code               4034101
_reflns_odcompleteness_completeness 99.78
_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:
 C13(H13), C5(H5), C7(H7), C10(H10), C11(H11), C8(H8)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 1.882
_oxdiff_exptl_absorpt_empirical_full_min 0.454