Rh(III)-Catalyzed Diastereoselective Annulation of Amides with Quinone Monoacetals: Access to Bridged Nine-Membered Heterocycles via C-H Activation.
Yang, Wei; Dong, Jinhuan; Wang, Jingyi; Xu, Xianxiu; Organic letters 19 (2017) 616–619; doi:10.1021/acs.orglett.6b03777

data_1545218
_publ_section_title
;
 Rh(III)-Catalyzed Diastereoselective Annulation of Amides with Quinone
 Monoacetals: Access to Bridged Nine-Membered Heterocycles via C-H
 Activation.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              616
_journal_page_last               619
_journal_paper_doi               10.1021/acs.orglett.6b03777
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C16 H21 N O5'
_chemical_formula_sum            'C16 H21 N O5'
_chemical_formula_weight         307.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                94.564(6)
_cell_angle_beta                 93.056(5)
_cell_angle_gamma                105.075(6)
_cell_formula_units_Z            2
_cell_length_a                   6.887(2)
_cell_length_b                   9.504(3)
_cell_length_c                   11.467(4)
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.224
_cell_measurement_theta_min      2.230
_cell_volume                     720.3(4)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4325
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.79
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7727
_exptl_absorpt_correction_T_min  0.470523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0555 before and 0.0320 after correction.
The Ratio of minimum to maximum transmission is 0.4705.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1608
_reflns_number_gt                2300
_reflns_number_total             3192
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03777_si_002.cif
_cod_data_source_block           za157m
_cod_depositor_comments
;

2019-03-26
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H21 N O5)'
_cod_original_formula_sum        'C32 H42 N2 O10'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     614.68
_cod_database_code               1545218
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H12 of C12, H10 of C10, H7 of C7, H15 of C15, H16 of C16,
   H18 of C18, H19 of C19
 At 1.5 times of:
  All C(H,H,H) groups, H20A of C20, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), C20(H20A)
;
_olex2_submission_special_instructions 'No special instructions were received'