Expedient access to substituted 3-amino-2-cyclopentenones by dirhodium-catalyzed [3+2]-annulation of silylated ketene imines and enoldiazoacetates
Xichen Xu; John S. Leszczynski; Savannah M. Mason; Peter Y. Zavalij; Michael P. Doyle; Chem.Commun. 50 (2014) 2462–; doi:10.1039/c3cc48993k

data_7112037
_publ_section_title
;
 Expedient access to substituted 3-amino-2-cyclopentenones by
 dirhodium-catalyzed [3+2]-annulation of silylated ketene imines and
 enoldiazoacetates
;
_journal_name_full               Chem.Commun.
_journal_page_first              2462
_journal_paper_doi               10.1039/c3cc48993k
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C20 H19 N O3'
_chemical_formula_sum            'C20 H19 N O3'
_chemical_formula_weight         321.36
_chemical_name_systematic
;
Organic compound, XXU
;
_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_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2012 & ZCIF'
_cell_angle_alpha                102.7775(16)
_cell_angle_beta                 103.9647(16)
_cell_angle_gamma                102.1013(16)
_cell_formula_units_Z            4
_cell_length_a                   10.4622(11)
_cell_length_b                   12.7512(13)
_cell_length_c                   13.6245(14)
_cell_measurement_reflns_used    9550
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.2
_cell_volume                     1652.4(3)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        'Apex2, Saint'
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  'Apex2, SHELXL-2012'
_computing_structure_refinement  'ShelXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'ShelXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex II diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0289316
_diffrn_orient_matrix_UB_12      0.0662905
_diffrn_orient_matrix_UB_13      0.0636534
_diffrn_orient_matrix_UB_21      0.0977927
_diffrn_orient_matrix_UB_22      -0.0007633
_diffrn_orient_matrix_UB_23      0.0110577
_diffrn_orient_matrix_UB_31      0.0106055
_diffrn_orient_matrix_UB_32      0.0511165
_diffrn_orient_matrix_UB_33      -0.0453587
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20066
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.980
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         7602
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0100P)^2^+0.9793P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6333
_reflns_number_total             7602
_reflns_threshold_expression     'I > 2\s(I)'
_iucr_refine_instructions_details 'Available on request'
_cod_data_source_file            c3cc48993k.txt
_cod_data_source_block           2467
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7112037
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.992