Rhodium(III)-Catalyzed Enantioselective C–H Activation/Annulation of Ferrocenecarboxamides with Internal Alkynes
Wang, Quannan; Nie, Yu-Han; Liu, Chen-Xu; Zhang, Wen-Wen; Wu, Zhi-Jie; Gu, Qing; Zheng, Chao; You, Shu-Li; ACS Catalysis  (2022) 3083–3093; doi:10.1021/acscatal.2c00083

data_4519329
_publ_section_title
;
 Rhodium(III)-Catalyzed Enantioselective C--H Activation/Annulation of
 Ferrocenecarboxamides with Internal Alkynes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              3083
_journal_page_last               3093
_journal_paper_doi               10.1021/acscatal.2c00083
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H19 Fe N O3'
_chemical_formula_sum            'C22 H19 Fe N O3'
_chemical_formula_weight         401.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.1970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.78120(10)
_cell_length_b                   22.3955(5)
_cell_length_c                   12.8222(2)
_cell_measurement_reflns_used    9012
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.81
_cell_measurement_theta_min      5.88
_cell_volume                     1879.19(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      193.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17175
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.885
_diffrn_reflns_theta_min         3.107
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.439
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1192 before and 0.0860 after correction. The Ratio of minimum to maximum transmission is 0.6372. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         6785
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0511P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5675
_reflns_number_total             6785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs2c00083_si_002.cif
_cod_data_source_block           mj21281_0m
_cod_database_code               4519329
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.809
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8348(18)
 0.1652(18)
2. 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
3. Uiso/Uaniso restraints and constraints
C38 \\sim C39 \\sim C40 \\sim C43 \\sim C44: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
O2 \\sim O3 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim
C22: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a :
 C40(C39,C38,C43,C44)
4.b Ternary CH refined with riding coordinates:
 C17(H17)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), N2(H2A), C24(H24), C25(H25), C26(H26),
 C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C39(H39), C38(H38), C43(H43),
  C44(H44)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C22(H22A,H22B,H22C), C31(H31A,H31B,H31C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              97363
_shelx_hkl_checksum              32795
_shelx_fab_checksum              71913
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'