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_4121849
_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_formula_moiety         'C23 H17 Cl O'
_chemical_formula_sum            'C23 H17 Cl O'
_chemical_formula_weight         344.82
_chemical_name_common            LMINC149
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2014-03-21T13:24:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                92.536(3)
_cell_angle_beta                 92.369(3)
_cell_angle_gamma                96.834(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1758(4)
_cell_length_b                   9.4495(5)
_cell_length_c                   9.8699(5)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.88
_cell_measurement_theta_min      2.24
_cell_measurement_wavelength     0.71073
_cell_volume                     847.94(7)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.985
_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      -0.011003
_diffrn_orient_matrix_UB_12      -0.008555
_diffrn_orient_matrix_UB_13      0.099784
_diffrn_orient_matrix_UB_21      -0.027857
_diffrn_orient_matrix_UB_22      -0.105278
_diffrn_orient_matrix_UB_23      -0.014859
_diffrn_orient_matrix_UB_31      0.105722
_diffrn_orient_matrix_UB_32      -0.015205
_diffrn_orient_matrix_UB_33      0.011428
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42617
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.985
_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         35.129
_diffrn_reflns_theta_min         2.068
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     277
_refine_ls_number_reflns         7415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.1258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                5411
_reflns_number_total             7415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5034952_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4121849--4121851.cif.'
_cod_database_code               4121849
_shelx_estimated_absorpt_t_min   0.852
_shelx_estimated_absorpt_t_max   0.934