Aldehydes and ketones as dipolarophiles: application to the synthesis of oxapenams
Andrews, Mark D.; Brown, Giles A.; Charmant, Jonathan P. H.; Peakman, Torren M.; Rebello, Arlene; Walsh, Kenneth E.; Gallagher, Timothy; Hales, Neil J.; Chemical Communications  (1999) 249–; doi:10.1039/a808688e

data_7110409
_publ_section_title
;
 Aldehydes and ketones as dipolarophiles: application to the synthesis of
 oxapenams
;
_journal_issue                   3
_journal_name_full               'Chemical Communications'
_journal_page_first              249
_journal_paper_doi               10.1039/a808688e
_journal_year                    1999
_chemical_formula_moiety         'C15 H10 F6 N2 O6'
_chemical_formula_sum            'C15 H10 F6 N2 O6'
_chemical_formula_weight         428.25
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   11.658(1)
_cell_length_b                   8.055(1)
_cell_length_c                   34.764(5)
_cell_measurement_reflns_used    243
_cell_measurement_temperature    173(2)
_cell_volume                     3264.5(7)
_computing_cell_refinement       'Bruker SMART v4'
_computing_data_collection       'Bruker SMART v4'
_computing_data_reduction        'Bruker SAINT v4'
_computing_molecular_graphics    'Bruker SHELXTL v6'
_computing_publication_material  'Bruker SHELXTL v6'
_computing_structure_refinement  'Bruker SHELXTL v6'
_computing_structure_solution    'Bruker SHELXTL v6'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       '\w scans'
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            13916
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
 Based on multiple and symmetry equivalent measurements using Bruker
 SADABS area detector and absorption correction software.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0018(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_ref   1.194
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0279P)^2^+1.8016P] where w=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                2108
_reflns_number_total             2344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            808688esup1.cif
_cod_data_source_block           oadbya
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3264.6(8)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7110409