Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes.
Seoane, Andrés; Casanova, Noelia; Quiñones, Noelia; Mascareñas, José L; Gulías, Moisés; Journal of the American Chemical Society 136 (2014) 7607–7610; doi:10.1021/ja5034952

data_4121851
_publ_section_title
;
 Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of
 2-Alkenylphenols and Alkynes.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7607
_journal_page_last               7610
_journal_paper_doi               10.1021/ja5034952
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H17 Br O'
_chemical_formula_sum            'C23 H17 Br O'
_chemical_formula_weight         389.27
_chemical_name_common            141F2
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_audit_creation_date             2014-02-03T13:58:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.410(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3833(11)
_cell_length_b                   7.9614(8)
_cell_length_c                   11.2213(12)
_cell_measurement_reflns_used    3983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      2.36
_cell_measurement_wavelength     0.71073
_cell_volume                     889.83(16)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.083129
_diffrn_orient_matrix_UB_12      -0.007645
_diffrn_orient_matrix_UB_13      -0.027945
_diffrn_orient_matrix_UB_21      -0.056255
_diffrn_orient_matrix_UB_22      -0.006414
_diffrn_orient_matrix_UB_23      -0.088379
_diffrn_orient_matrix_UB_31      0.002194
_diffrn_orient_matrix_UB_32      0.125208
_diffrn_orient_matrix_UB_33      -0.006234
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13416
_diffrn_reflns_point_group_measured_fraction_full 0.992
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_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.224
_diffrn_reflns_theta_min         1.892
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    2.317
_exptl_absorpt_correction_T_max  0.704
_exptl_absorpt_correction_T_min  0.57
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_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.51
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 1247 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.011(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3902
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0301P)^2^+0.1676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                3205
_reflns_number_total             3902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5034952_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4121849--4121851.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4121851
_shelx_estimated_absorpt_t_min   0.357
_shelx_estimated_absorpt_t_max   0.955