Diastereoselective conjugate addition of organocuprates to chiral racemic olefinic amido esters. Formal total synthesis of paroxetine
Cossy, Janine; Mirguet, Olivier; Pardo, Domingo Gomez; Desmurs, Jean-Roger; New Journal of Chemistry 27 (2003) 475–; doi:10.1039/b209181j

data_7050460
_publ_section_title
;
 Diastereoselective conjugate addition of organocuprates to chiral
 racemic olefinic amido esters. Formal total synthesis of paroxetine
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              475
_journal_paper_doi               10.1039/b209181j
_journal_volume                  27
_journal_year                    2003
_chemical_compound_source
;
?
;
_chemical_formula_moiety         ' C41 H49 S1 F1 N2 O7 '
_chemical_formula_sum            'C41 H49 F N2 O7 S'
_chemical_formula_weight         732.91
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             01-03-08
_audit_creation_method           CRYSTALS
_cell_angle_alpha                66.36(3)
_cell_angle_beta                 73.83(4)
_cell_angle_gamma                72.44(3)
_cell_formula_units_Z            2
_cell_length_a                   11.849(7)
_cell_length_b                   12.894(3)
_cell_length_c                   14.747(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      10.2
_cell_measurement_theta_min      10
_cell_volume                     1935.5(16)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction
;
RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994)
;
_computing_molecular_graphics
;
CAMERON (Watkin, Prout & Pearce,  1996)
;
_computing_publication_material
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_structure_refinement
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_diffrn_ambient_temperature      295
_diffrn_measurement_device       ' Enraf-nonius CAD4 '
_diffrn_measurement_method       2\q/\w
_diffrn_radiation_monochromator  ' graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.02
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7147
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1
_diffrn_standards_decay_%        7.65
_diffrn_standards_interval_time  3600
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.13
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            ' none '
_exptl_crystal_density_diffrn    1.26
_exptl_crystal_description       'plate '
_exptl_crystal_F_000             780.44
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.00
_refine_diff_density_min         -0.91
_refine_ls_extinction_coef       549
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_goodness_of_fit_obs   1.1397
_refine_ls_hydrogen_treatment
;
H atoms placed geometrically after each cycle,
one overall isotropic thermal parameter refined
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         3163
_refine_ls_R_factor_obs          0.0549
_refine_ls_shift/esd_max         12.134171
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
;
Chebychev polynomial (Carruthers & Watkin, 1979)
;
_refine_ls_wR_factor_obs         0.0670
_reflns_number_observed          3163
_reflns_number_total             6786
_reflns_observed_criterion       >3.00\s(I)
_cod_data_source_file            b209181j.txt
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic ' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_matrix_type' value ' full' changed to 'full'
according to '/home/adriana/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_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_cell_measurement_temperature' value '295K' was changed to '295' -
the value should be numeric and without a unit
designator.

'_diffrn_ambient_temperature' value '295K' was changed
to '295' - the value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct_Methods' was changed to
'direct'.

'_atom_sites_solution_hydrogens' value ' Geometric' was changed to
'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        1936(2)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        ' C41 H49 S1 F1 N2 O7'
_cod_database_code               7050460