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_7204983
_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            'C24 H24 N2 O3 S'
_chemical_formula_weight         420.51
_chemical_melting_point          378.5(5)
_chemical_name_systematic
; 
(3S,4R,1'S)-1-Benzyl-3-[1-(benzyloxycarbonylamino)ethyl]-4-(2-thienyl)-
azetidin-2-one 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 90.117(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2101(5)
_cell_length_b                   20.7429(10)
_cell_length_c                   11.5524(6)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      22.5
_cell_volume                     2207.0(2)
_computing_cell_refinement       'SIEMENS XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS and XEMP'
_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       'Siemens P4'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7539
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         3.83
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plates
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_coef       0.0075(3)
_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   1.169
_refine_ls_goodness_of_fit_obs   1.206
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         6660
_refine_ls_number_restraints     317
_refine_ls_restrained_S_all      1.263
_refine_ls_restrained_S_obs      1.192
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_obs          0.0790
_refine_ls_shift/esd_max         -0.033
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1483P)^2^+0.5129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2715
_refine_ls_wR_factor_obs         0.2244
_reflns_number_observed          5301
_reflns_number_total             6870
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b105748k.txt
_cod_data_source_block           s549rc2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Psi- Scan' changed to 'psi-scan'
according to '/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '378 - 379 K' was changed to
'378.5(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^)+(0.1483P)^2^+0.5129P] 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^)+(0.1483P)^2^+0.5129P] 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)
_cod_database_code               7204983