Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes
Chen, Chao; Shi, Chen; Yang, Yaxi; Zhou, Bing; Chemical Science  (2020) –; doi:10.1039/D0SC04007J

data_1559366
_publ_section_title
;
 Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of
 aromatic tethered alkenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04007J
_journal_year                    2020
_chemical_formula_moiety         'C19 H26 N2 O5'
_chemical_formula_sum            'C19 H26 N2 O5'
_chemical_formula_weight         362.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-13 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                65.847(2)
_cell_angle_beta                 89.484(2)
_cell_angle_gamma                80.357(2)
_cell_formula_units_Z            4
_cell_length_a                   9.7686(7)
_cell_length_b                   14.2286(10)
_cell_length_c                   15.2461(11)
_cell_measurement_reflns_used    1717
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.128
_cell_measurement_theta_min      2.413
_cell_volume                     1902.1(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_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_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7423
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.378
_diffrn_reflns_theta_min         2.119
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.3516
_exptl_absorpt_correction_T_min  0.2516
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 26391 reflections, Rint = 0.0678
 (9093 with I > 3sig(I), Rint = 0.0371)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         7423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0710
_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^)+(0.0522P)^2^+1.1663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4703
_reflns_number_total             7423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04007j2.cif
_cod_data_source_block           mo_22020391_0m_4
_cod_database_code               1559366
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C4(H4A,H4B), C26(H26A,H26B), C10(H10A,H10B), C28(H28A,H28B),
 C23(H23A,H23B), C21(H21A,H21B), C2(H2A,H2B), C20(H20A,H20B), C1(H1A,H1B),
 C24(H24A,H24B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3A), N2(H2), C14(H14), C33(H33), C13(H13), C34(H34), C32(H32), C15(H15)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C29(H29A,H29B,H29C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_olex2_submission_special_instructions 'No special instructions were received'