Unique Michael addition-initiated domino reaction for the stereoselective synthesis of functionalized macrolactones from alpha-nitroketones in water.
Giorgi, Giorgio; Miranda, Sonia; López-Alvarado, Pilar; Avendaño, Carmen; Rodriguez, Jean; Menéndez, J Carlos; Organic letters 7 (2005) 2197–2200; doi:10.1021/ol0505860

data_1506572
_publ_section_title
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 Unique Michael addition-initiated domino reaction for the stereoselective
 synthesis of functionalized macrolactones from alpha-nitroketones in
 water.
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_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2197
_journal_page_last               2200
_journal_paper_doi               10.1021/ol0505860
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C12 H19 N O4'
_chemical_formula_sum            'C12 H19 N O4'
_chemical_formula_weight         241.28
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 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                 96.29(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.687(2)
_cell_length_b                   7.6780(15)
_cell_length_c                   28.810(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      8
_cell_volume                     2349.8(8)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'SEIFERT XRD 3003 SC'
_diffrn_measurement_method       2theta-omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1480
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            1721
_diffrn_reflns_theta_full        60.02
_diffrn_reflns_theta_max         60.02
_diffrn_reflns_theta_min         1.42
_diffrn_standards_decay_%        'no decay, variation 0.5'
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0313(42)
_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   1.076
_refine_ls_goodness_of_fit_obs   1.529
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_restrained_S_obs      1.529
_refine_ls_R_factor_all          0.2185
_refine_ls_R_factor_obs          0.0919
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2781
_refine_ls_wR_factor_obs         0.1988
_reflns_number_observed          546
_reflns_number_total             1721
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ol0505860si20050317_102019.cif
_cod_data_source_block           josefin
_cod_depositor_comments
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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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_original_sg_symbol_H-M      I2/a
_cod_database_code               1506572