A Double Decarboxylation Reaction of an Oxazolidinone and Carboxylic Acid: Its Application to the Synthesis of a New Opioid Lead Compound
Fujii, Hideaki; Imaide, Satomi; Watanabe, Akio; Yoza, Kenji; Nakajima, Mayumi; Nakao, Kaoru; Mochizuki, Hidenori; Sato, Noriko; Nemoto, Toru; Nagase, Hiroshi; Journal of Organic Chemistry 75 (2010) 995–998; doi:10.1021/jo9025463

data_4028967
_publ_section_title
;
 A Double Decarboxylation Reaction of an Oxazolidinone and Carboxylic
 Acid: Its Application to the Synthesis of a New Opioid Lead Compound
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   3
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              995
_journal_page_last               998
_journal_paper_doi               10.1021/jo9025463
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C21 H25 N O4'
_chemical_formula_weight         355.42
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.901(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.109(5)
_cell_length_b                   5.1775(16)
_cell_length_c                   20.234(6)
_cell_measurement_reflns_used    3308
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.45
_cell_volume                     1739.9(9)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0838
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19258
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(11)
_refine_ls_extinction_coef       0.0022(13)
_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   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         7420
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                5316
_reflns_number_total             7420
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4025213
_cod_data_source_file            jo9025463sup1.cif
_cod_data_source_block           p21
_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.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               4028967