Rhodium-Catalyzed Synthesis of 3-Hydroxy-β-lactams via Oxonium Ylide Generation: Three-Component Reaction between Azetidine-2,3-diones, Ethyl Diazoacetate, and Alcohols
Benito Alcaide; Pedro Almendros; Cristina Aragoncillo; Ricardo Callejo; M. Pilar Ruiz; M. Rosario Torres; Journal of Organic Chemistry 74 (2009) 8421–8424; doi:10.1021/jo9019013

data_4024971
_publ_section_title
;
Rhodium-Catalyzed Synthesis of 3-Hydroxy-\b-lactams via Oxonium Ylide
Generation: Three-Component Reaction between Azetidine-2,3-diones, Ethyl
Diazoacetate, and Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8421
_journal_page_last               8424
_journal_paper_doi               10.1021/jo9019013
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C19 H25 N O7'
_chemical_formula_weight         379.40
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5776(7)
_cell_length_b                   13.9511(17)
_cell_length_c                   25.656(3)
_cell_measurement_reflns_used    1297
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15.15
_cell_measurement_theta_min      2.92
_cell_volume                     1996.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_sigmaI/netI    0.1614
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15396
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3507
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_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                1340
_reflns_number_total             3507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9019013_si_003.cif
_cod_data_source_block           rm327a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4024971