Rhodium-catalyzed oxidative C-H/C-H cross-coupling of aniline with heteroarene: N-nitroso group enabled mild conditions.
He, Shuang; Tan, Guangying; Luo, Anping; You, Jingsong; Chemical communications (Cambridge, England) 54 (2018) 7794–7797; doi:10.1039/c8cc04027c

data_7121853
_publ_section_title
;
 Rhodium-catalyzed oxidative C-H/C-H cross-coupling of aniline with
 heteroarene: N-nitroso group enabled mild conditions.
;
_journal_issue                   56
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7794
_journal_page_last               7797
_journal_paper_doi               10.1039/c8cc04027c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C17 H21 Br Cl N2 O Rh'
_chemical_formula_sum            'C17 H21 Br Cl N2 O Rh'
_chemical_formula_weight         487.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-19
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_audit_update_record
;
2018-04-19 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.4304(5)
_cell_length_b                   14.9823(4)
_cell_length_c                   16.4747(5)
_cell_measurement_reflns_used    8490
_cell_measurement_temperature    295.4(2)
_cell_measurement_theta_max      72.5440
_cell_measurement_theta_min      4.0050
_cell_volume                     3808.7(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.4(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  150.0000 84

  2 omega  -32.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000  -30.0000 95

  3 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  -60.0000 66

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000 -180.0000 74

  5 omega  -32.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000   30.0000 95

  6 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000 -120.0000 66

  7 omega  -33.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421    0.0000 -120.0000 138

  8 omega   91.00  176.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

  9 omega   38.00   91.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 10 omega   40.00  135.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 95

 11 omega   40.00   98.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 12 omega  100.00  178.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 78

 13 omega  100.00  178.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

 14 omega   40.00   98.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 15 omega   53.00   98.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 45

 16 omega   91.00  174.00   1.0000    3.6100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0264366000
_diffrn_orient_matrix_UB_12      -0.0550776000
_diffrn_orient_matrix_UB_13      -0.0750445000
_diffrn_orient_matrix_UB_21      -0.0847893000
_diffrn_orient_matrix_UB_22      -0.0537153000
_diffrn_orient_matrix_UB_23      0.0061580000
_diffrn_orient_matrix_UB_31      -0.0452968000
_diffrn_orient_matrix_UB_32      0.0684861000
_diffrn_orient_matrix_UB_33      -0.0554027000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19343
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.913
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.335
_refine_diff_density_min         -1.811
_refine_diff_density_rms         0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0555
_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^)+(0.1042P)^2^+4.6260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3105
_reflns_number_total             3400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04027c2.cif
_cod_data_source_block           hs-x-2
_cod_depositor_comments          'Adding full bibliography for 7121853.cif.'
_cod_original_cell_volume        3808.67(19)
_cod_database_code               7121853
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Rigid bond restraints
 C00A, C00C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C00A \\sim C00C: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C00A) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of
0.0002
4.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00L(H00O)
4.b Idealised Me refined as rotating group:
 C00G(H00A,H00C,H00E), C00H(H00F,H00G,H00H), C00J(H00I,H00J,H00K), C00K(H00L,
 H00M,H00N), C00M(H00P,H00Q,H00R), C00N(H00S,H00T,H00U)
;
_olex2_submission_special_instructions 'No special instructions were received'