Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines with two molecules of a diazo ketone
Xinfang Xu; Xichen Xu; Peter Y. Zavalij; Michael P. Doyle; Chem.Commun. 49 (2013) 2762–; doi:10.1039/c3cc41119b

data_7109035
_publ_section_title
;
 Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines
 with two molecules of a diazo ketone
;
_journal_name_full               Chem.Commun.
_journal_page_first              2762
_journal_paper_doi               10.1039/c3cc41119b
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C22 H25 Cl N2 O3'
_chemical_formula_sum            'C22 H25 Cl N2 O3'
_chemical_formula_weight         400.89
_chemical_name_common            Organic
_chemical_name_systematic
;
Organic
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 & ZCIF'
_cell_angle_alpha                90
_cell_angle_beta                 93.9007(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.604(3)
_cell_length_b                   16.7235(18)
_cell_length_c                   10.4891(11)
_cell_measurement_reflns_used    13752
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.4
_cell_volume                     4130.9(8)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  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_detector_type            'Bruker Smart Apex II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0109723
_diffrn_orient_matrix_UB_12      -0.0514762
_diffrn_orient_matrix_UB_13      -0.0401080
_diffrn_orient_matrix_UB_21      0.0377478
_diffrn_orient_matrix_UB_22      0.0232822
_diffrn_orient_matrix_UB_23      -0.0171946
_diffrn_orient_matrix_UB_31      0.0160586
_diffrn_orient_matrix_UB_32      -0.0195847
_diffrn_orient_matrix_UB_33      0.0850121
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         1.729
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1696
_exptl_crystal_id                'Doyle-XinFangxu XXU-NNC-U 150K'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0100P)^2^+4.7000P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5174
_reflns_number_total             6039
_reflns_threshold_expression     'I > 2\s(I)'
_iucr_refine_instructions_details 'See _shelx_res_file'
_cod_data_source_file            c3cc41119b.txt
_cod_data_source_block           2347
_cod_database_code               7109035
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.967
_diffrn_reflns_sigmai/neti       0.0151