Diazoketones as precursors in Î²-lactam synthesis. New insights into the mechanism of the photochemically induced Staudinger reaction
Linder, Michael R.; Frey, Wolfgang U.; Podlech, Joachim; Journal of the Chemical Society, Perkin Transactions 1  (2001) 2566–; doi:10.1039/b105748k

data_7204976
_publ_contact_author             ' Joachim Podlech'
_publ_section_title
;
 Diazoketones as precursors in \^I&#x00B2;-lactam synthesis. New
 insights into the mechanism of the photochemically induced Staudinger
 reaction
;
_journal_issue                   20
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2566
_journal_paper_doi               10.1039/b105748k
_journal_year                    2001
_chemical_formula_sum            'C26 H25 N3 O5'
_chemical_formula_weight         459.49
_chemical_melting_point          433.5(5)
_chemical_name_systematic
; 
(3S,4R,1'S)-1-Benzyl-3-[1-(benzyloxycarbonylamino)ethyl]-4-
(4-nitrophenyl)-azetidin-2-one
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.312(2)
_cell_length_b                   9.733(2)
_cell_length_c                   26.550(6)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      12
_cell_volume                     2406.3(9)
_computing_cell_refinement       'Siemens P3/V Data Collection System'
_computing_data_collection       'Siemens P3/V Data Collection System'
_computing_data_reduction        'SHELXTL plus - XDISK'
_computing_molecular_graphics    'SHELXTL - XP'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nicolet P3'
_diffrn_measurement_method       'Wyckoff - Scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3146
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.53
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       plates
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.52(238)
_refine_ls_extinction_coef       0.0112(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.037
_refine_ls_goodness_of_fit_obs   1.155
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_restrained_S_obs      1.155
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_obs          0.0545
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.7171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1412
_refine_ls_wR_factor_obs         0.1060
_reflns_number_observed          1837
_reflns_number_total             3146
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b105748k.txt
_cod_data_source_block           s545rm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '433 - 434 K' was changed to
'433.5(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.7171P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.7171P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7204976