Ruthenium(II)-Catalyzed Distal Weak O-Coordinating C-H Alkylation of Arylacetamides with Alkenes: Combined Experimental and DFT Studies.
Sivasakthikumaran, Ramakrishnan; Jambu, Subramanian; Jeganmohan, Masilamani; The Journal of organic chemistry 84 (2019) 3977–3989; doi:10.1021/acs.joc.8b03257

data_4034225
_publ_section_title
;
 Ruthenium(II)-Catalyzed Distal Weak O-Coordinating C-H Alkylation of
 Arylacetamides with Alkenes: Combined Experimental and DFT Studies.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3977
_journal_page_last               3989
_journal_paper_doi               10.1021/acs.joc.8b03257
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H20 Br N O3'
_chemical_formula_sum            'C16 H20 Br N O3'
_chemical_formula_weight         354.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.674(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0330(7)
_cell_length_b                   15.1328(8)
_cell_length_c                   7.9409(3)
_cell_measurement_reflns_used    3819
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      2.69
_cell_volume                     1548.24(13)
_computing_data_collection       'Bruker APEX2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0479
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.581
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.665
_exptl_absorpt_correction_T_max  0.726
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       Block
_exptl_crystal_F_000             728
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0385
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0654P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1896
_reflns_number_total             2732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03257_si_002.cif
_cod_data_source_block           6ha
_cod_database_code               4034225
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.740
_shelx_estimated_absorpt_t_min   0.456
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'