Overcoming naphthoquinone deactivation: rhodium-catalyzed C-5 selective C‒H iodination as a gateway to functionalized derivatives
Jardim, Guilherme A. M.; da Silva Júnior, Eufrânio N.; Bower, John F.; Chem. Sci. 7 (2016) 3780–; doi:10.1039/C6SC00302H

data_1542605
_publ_section_title
;
 Overcoming naphthoquinone deactivation: rhodium-catalyzed C-5 selective
 C--H iodination as a gateway to functionalized derivatives
;
_journal_issue                   6
_journal_name_full               'Chem. Sci.'
_journal_page_first              3780
_journal_paper_doi               10.1039/C6SC00302H
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C20 H24 Cl4 F6 Rh2'
_chemical_formula_sum            'C20 H24 Cl4 F6 Rh2'
_chemical_formula_weight         726.01
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   28.1638(9)
_cell_length_b                   28.1638(9)
_cell_length_c                   8.1635(3)
_cell_measurement_reflns_used    2440
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.50
_cell_volume                     5607.8(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.868
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.1233
_diffrn_reflns_Laue_measured_fraction_full 0.868
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13326
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.949
_diffrn_reflns_theta_min         2.505
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1418 before and 0.0785 after correction.
The Ratio of minimum to maximum transmission is 0.7677.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_description       block
_exptl_crystal_F_000             3204
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.611
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.611
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1778
_reflns_number_total             2667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00302h2.cif
_cod_data_source_block           testr1
_cod_depositor_comments
'Adding full bibliography for 1542604--1542615.cif.'
_cod_original_cell_volume        5607.7(4)
_cod_database_code               1542605
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              47028
_olex2_submission_special_instructions 'No special instructions were received'