Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and Amidation Reactions of N-Phenoxyacetamides.
Wu, Yunxiang; Chen, Zhaoqiang; Yang, Yaxi; Zhu, Weiliang; Zhou, Bing; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b10349

data_4126948
_publ_section_title
;
 Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and
 Amidation Reactions of N-Phenoxyacetamides.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b10349
_journal_year                    2017
_chemical_formula_moiety         'C13 H14 Br N O6'
_chemical_formula_sum            'C13 H14 Br N O6'
_chemical_formula_weight         360.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                92.744(2)
_cell_angle_beta                 90.917(2)
_cell_angle_gamma                111.231(2)
_cell_formula_units_Z            4
_cell_length_a                   7.8925(5)
_cell_length_b                   10.6053(8)
_cell_length_c                   18.5694(12)
_cell_measurement_reflns_used    2224
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.28
_cell_volume                     1446.22(17)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13221
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_min         2.064
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.869
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0857 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.8028. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0640P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4555
_reflns_number_total             6557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b10349_si_002.cif
_cod_data_source_block           mo_2017375wyx0517_0m
_cod_database_code               4126948
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C14(H14), C16(H16), C1(H1A)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C11(H11A,H11B,
 H11C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O8(H8), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'