Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N-Heterobicyclic Enones
Megan H. Shaw; Ekaterina Y. Melikhova; Daniel P. Kloer; William G. Whittingham; John F. Bower; Journal of the American Chemical Society 135 (2013) 4992–4995; doi:10.1021/ja401936c

data_4119551
_publ_section_title
;
 Directing Group Enhanced Carbonylative Ring Expansions of
 Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent
 Synthesis of N-Heterobicyclic Enones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4992
_journal_page_last               4995
_journal_paper_doi               10.1021/ja401936c
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C8 H11.56 Cl0.89 N0.89 O3.56 Rh0.89'
_chemical_formula_sum            'C8 H11.56 Cl0.89 N0.89 O3.56 Rh0.89'
_chemical_formula_weight         300.06
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 119.202(3)
_cell_angle_gamma                90
_cell_formula_units_Z            9
_cell_length_a                   19.6360(4)
_cell_length_b                   12.1674(2)
_cell_length_c                   11.4299(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2383.75(10)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5083
_diffrn_reflns_theta_full        58.909
_diffrn_reflns_theta_max         58.909
_diffrn_reflns_theta_min         4.456
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_F_000             1344
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9942
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0189
_refine_ls_shift/su_max          0.0014675
_refine_ls_shift/su_mean         9.4604130
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.59P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0503
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0501
_reflns_limit_h_max              18
_reflns_limit_h_min              -21
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1594
_reflns_number_total             1710
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.11
_oxford_diffrn_Wilson_scale      0.45
_oxford_refine_ls_r_factor_ref   0.0208
_oxford_refine_ls_scale          1.573(7)
_oxford_reflns_number_all        1699
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ja401936c_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               4119551