Regio and diastereoselective lactonisation of enolisable 1,3-dicarbonyls by reaction with mesoionic 1,3-oxazolium-5-olates
Grassi, Giovanni; Risitano, Francesco; Foti, Francesco; Cordaro, Massimiliano; Bruno, Giuseppe; Nicolò, Francesco; Chemical Communications (Cambridge, United Kingdom)  (2003) 1868–1869; doi:10.1039/b304560a

data_7113512
_publ_section_title
;
 Regio and diastereoselective lactonisation of enolisable 1,3-dicarbonyls
 by reaction with mesoionic 1,3-oxazolium-5-olates
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   15
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1868
_journal_page_last               1869
_journal_paper_doi               10.1039/b304560a
_journal_year                    2003
_chemical_absolute_configuration unk
_chemical_compound_source        'chemical synthesys'
_chemical_formula_moiety         'C26 H27 N O4'
_chemical_formula_sum            'C26 H27 N O4'
_chemical_formula_weight         417.49
_chemical_name_systematic
; 
N-Methyl-N-(3,7,7-trimethyl-2,5-dioxo-4-phenyl-3,4,5,6,7,8-hexahydro-2H
-chromen-3-yl)-benzamide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_date             17-APR-2003
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.587(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3788(9)
_cell_length_b                   6.4952(7)
_cell_length_c                   16.451(2)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      34.959
_cell_measurement_theta_min      14.320
_cell_volume                     1107.9(2)
_computing_cell_refinement       'XSCANS '
_computing_data_collection       'XSCANS (Bruker,1999)'
_computing_data_reduction        'XSCANS '
_computing_molecular_graphics    'XPW (Siemens, 1996)'
_computing_publication_material  'PARST97 (Nardelli, 1995) and SHELXL-97'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1994)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4 diffractometer'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3734
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.26619
_exptl_absorpt_correction_T_min  0.24474
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
\y scan method among Kopfmann & Huber, 1968
;
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_preparation       're-crystallized from methanol solution'
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_coef       0.035(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   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.1511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2114
_reflns_number_total             2771
_reflns_threshold_expression     >2\s(I)
_cod_duplicate_entry             7103820
_cod_data_source_file            b304560a.txt
_cod_data_source_block           risi33
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7113512