Formal synthesis of belactosin A and hormaomycin via a diastereoselective intramolecular cyclopropanation of an alpha-nitro diazoester.
Vanier, Sébastien F; Larouche, Guillaume; Wurz, Ryan P.; Charette, André B; Organic letters 12 (2010) 672–675; doi:10.1021/ol9026528

data_1503381
_publ_section_title
;
 Formal synthesis of belactosin A and hormaomycin via a diastereoselective
 intramolecular cyclopropanation of an alpha-nitro diazoester.
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_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              672
_journal_page_last               675
_journal_paper_doi               10.1021/ol9026528
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C15 H12 N2 O6'
_chemical_formula_sum            'C15 H12 N2 O6'
_chemical_formula_weight         316.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 96.892(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9683(5)
_cell_length_b                   11.3211(4)
_cell_length_c                   8.1328(3)
_cell_measurement_reflns_used    4230
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      68.50
_cell_measurement_theta_min      2.97
_cell_volume                     1368.21(8)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18815
_diffrn_reflns_theta_full        68.89
_diffrn_reflns_theta_max         68.89
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         72
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_T_max  0.9600
_exptl_absorpt_correction_T_min  0.8500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0961P)^2^+0.0589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                1788
_reflns_number_total             2491
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol9026528_si_002.cif
_cod_data_source_block           cha129
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (26
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (41
time).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (60 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1503381