Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation.
Jardim, Guilherme A. M.; Bower, John F.; da Silva Júnior, Eufrânio N; Organic letters 18 (2016) 4454–4457; doi:10.1021/acs.orglett.6b01586

data_1555619
_publ_section_title
;
 Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H
 Iodination, Bromination, and Phenylselenation.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4454
_journal_page_last               4457
_journal_paper_doi               10.1021/acs.orglett.6b01586
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C7 H5 I O3'
_chemical_formula_sum            'C7 H5 I O3'
_chemical_formula_weight         264.01
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0841(2)
_cell_length_b                   14.9751(3)
_cell_length_c                   6.26290(10)
_cell_measurement_reflns_used    6284
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.720
_cell_volume                     758.19(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, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11893
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.114
_diffrn_reflns_theta_min         2.720
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.174
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0643 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.8186.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.313
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.039(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         2225
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0150
_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^)+(0.0123P)^2^+0.2322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0305
_refine_ls_wR_factor_ref         0.0316
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                1999
_reflns_number_total             2225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01586_si_003.cif
_cod_data_source_block           gj218
_cod_database_code               1555619
_shelxl_version_number           2013-4
_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:
 C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              73106
_shelx_hkl_checksum              85885
_olex2_submission_special_instructions 'No special instructions were received'