Flow Rhodaelectro-Catalyzed Alkyne Annulations by Versatile C-H Activation: Mechanistic Support for Rhodium(III/IV).
Kong, Wei-Jun; Finger, Lars H.; Messinis, Antonis M.; Kuniyil, Rositha; Oliveira, João C A; Ackermann, Lutz; Journal of the American Chemical Society 141 (2019) 17198–17206; doi:10.1021/jacs.9b07763

data_4127879
_publ_section_title
;
 Flow Rhodaelectro-Catalyzed Alkyne Annulations by Versatile C-H
 Activation: Mechanistic Support for Rhodium(III/IV).
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17198
_journal_page_last               17206
_journal_paper_doi               10.1021/jacs.9b07763
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C20 H26 N O3 Rh'
_chemical_formula_sum            'C20 H26 N O3 Rh'
_chemical_formula_weight         431.33
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.7240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3525(4)
_cell_length_b                   10.3586(4)
_cell_length_c                   14.6863(5)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.522
_cell_measurement_theta_min      2.405
_cell_volume                     1879.03(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34629
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.528
_diffrn_reflns_theta_min         2.406
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  0.2882
_exptl_absorpt_correction_T_min  0.2336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1191 before and 0.0349 after correction. The Ratio of minimum to maximum transmission is 0.8105. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.456
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0173
_refine_ls_R_factor_gt           0.0170
_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^)+(0.0181P)^2^+0.9747P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0437
_refine_ls_wR_factor_ref         0.0438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5605
_reflns_number_total             5703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07763_si_004.cif
_cod_data_source_block           0667_cg_0m
_cod_database_code               4127879
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.677
_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, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C10(H10D,H10E,H10F), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,
 H20B,H20C)
;
_shelx_res_checksum              92166
_shelx_hkl_checksum              23642
_olex2_submission_special_instructions 'No special instructions were received'