Recyclable rhodium-catalyzed C–H activation/[4 + 2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight
Meng, Haifang; Xu, Huiying; Zhou, Zhi; Tang, Zhenhao; Li, Yidi; Zhou, Yu; Yi, Wei; Wu, Xiaowei; Green Chemistry 24 (2022) 7012–7021; doi:10.1039/D2GC02347D

data_7245393
_publ_section_title
;
 Recyclable rhodium-catalyzed C--H activation/[4 + 2] annulation with
 unconventional regioselectivity at ambient temperature: experimental
 development and mechanistic insight
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              7012
_journal_page_last               7021
_journal_paper_doi               10.1039/D2GC02347D
_journal_volume                  24
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-04 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.541(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9187(10)
_cell_length_b                   12.6378(19)
_cell_length_c                   14.994(2)
_cell_measurement_reflns_used    1604
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.936
_cell_measurement_theta_min      2.735
_cell_volume                     1302.5(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      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_av_unetI/netI     0.1247
_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       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11327
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_min         2.113
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1297 before and 0.0802 after correction. The Ratio of minimum to maximum transmission is 0.8971. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 798 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4770
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0771P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1807
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.818
_reflns_Friedel_fraction_max     0.776
_reflns_number_gt                2663
_reflns_number_total             4770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02347d2.cif
_cod_data_source_block           mo_2022197_0m
_cod_depositor_comments          'Adding full bibliography for 7245393.cif.'
_cod_database_code               7245393
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. 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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), N1(H1), N2(H2), C12(H12), C31(H31), C10(H10), C11(H11), C3(H3),
 C30(H30), C1(H1B), C23(H23), C22(H22), C21(H21), C33(H33), C35(H35), C5(H5),
 C2(H2A), C32(H32), C13(H13), C4(H4A)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'