Pd(0)-Catalyzed Cross-Coupling of 1,1-Diboronates with 2,2'-Dibromobiphenyls: Synthesis of 9H-Fluorenes.
Xu, Shuai; Shangguan, Xianghang; Li, Huan; Zhang, Yan; Wang, Jianbo; The Journal of organic chemistry 80 (2015) 7779–7784; doi:10.1021/acs.joc.5b01100

data_4031285
_publ_section_title
;
 Pd(0)-Catalyzed Cross-Coupling of 1,1-Diboronates with
 2,2'-Dibromobiphenyls: Synthesis of 9H-Fluorenes.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7779
_journal_page_last               7784
_journal_paper_doi               10.1021/acs.joc.5b01100
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C21 H17 Cl'
_chemical_formula_sum            'C21 H17 Cl'
_chemical_formula_weight         304.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-11-02
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.210(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0568(11)
_cell_length_b                   5.3536(3)
_cell_length_c                   18.9471(12)
_cell_measurement_reflns_used    2448
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      27.8410
_cell_measurement_theta_min      4.0090
_cell_volume                     1577.99(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9957
_diffrn_measured_fraction_theta_max 0.8296
_diffrn_measurement_details
;
  1 omega  -65.00    9.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -38.0000  -30.0000 74

  2 omega  -88.00   15.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -38.0000 -180.0000 103
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0309878000
_diffrn_orient_matrix_UB_12      -0.0547644000
_diffrn_orient_matrix_UB_13      0.0341139000
_diffrn_orient_matrix_UB_21      -0.0264490000
_diffrn_orient_matrix_UB_22      -0.1071487000
_diffrn_orient_matrix_UB_23      -0.0060495000
_diffrn_orient_matrix_UB_31      0.0204451000
_diffrn_orient_matrix_UB_32      -0.0555417000
_diffrn_orient_matrix_UB_33      -0.0220046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6187
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.131
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description
;
;
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.2117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2409
_reflns_number_total             3105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01100_si_001.cif
_cod_data_source_block           exp_4327
_cod_depositor_comments          'Adding full bibliography for 4031285.cif.'
_cod_original_cell_volume        1578.00(18)
_cod_database_code               4031285
_chemical_oxdiff_formula         'C21 H16 Cl1'
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C20(H20), C21(H21)
;
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.954
_shelxl_version_number           2013-3