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_1559365
_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         'C26 H24 N3 O4, C2 H F3 O2, C2 F3 O2'
_chemical_formula_sum            'C30 H25 F6 N3 O8'
_chemical_formula_weight         669.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-06 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.2120(5)
_cell_length_b                   15.4949(5)
_cell_length_c                   20.0978(5)
_cell_measurement_reflns_used    8113
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.49
_cell_volume                     5982.9(3)
_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      170.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.981
_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  0.0581
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40460
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         1.969
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1028 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.9344. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6012
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+5.1210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4054
_reflns_number_total             6012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04007j2.cif
_cod_data_source_block           zz
_cod_database_code               1559365
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.980
_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. Restrained distances
 O5-H5A
 0.84 with sigma of 0.02
 F7-C30 \\sim F6-C30 \\sim F5-C30 \\sim F4-C30 \\sim F9-C30 \\sim F8-C30
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F8) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim
Ueq, Uanis(F4) \\sim Ueq, Uanis(F9) \\sim Ueq: with sigma of 0.005 and sigma
for terminal atoms of 0.01
4. Others
 Fixed Sof: F9(0.6) F5(0.6) F7(0.6) F4(0.4) F8(0.4) F6(0.4)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C15(H15), C14(H14), C5(H5), C25(H25), C21(H21), C1(H1A),
 C4(H4), C2(H2), C24(H24), C23(H23), C22(H22), C3(H3A)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'