Synthesis of Tricyclic Phosphonopyrrolidines via IMDAF: Experimental and Theoretical Investigation of the Observed Stereoselectivity
Diederica D. Claeys; Kristof Moonen; Bart I. Roman; Victor N. Nemykin; Viktor V. Zhdankin; Michel Waroquier; Veronique Van Speybroeck; Christian V. Stevens; Journal of Organic Chemistry 73 (2008) 7921–7927; doi:10.1021/jo801138s

data_4023726
_publ_contact_author_address
; 
 1039 University Drive, 
 Department of Chemistry & Biochemistry, 
 University of Minnesota Duluth, 
 Duluth, MN 55812, USA. 
;
_publ_contact_author_email       vnemykin@d.umn.edu
_publ_contact_author_fax         '+1 218 7267394'
_publ_contact_author_name        'Victor Nemykin'
_publ_contact_author_phone       '+1 218 7266729'
_publ_section_title
;
 Synthesis of Tricyclic Phosphonopyrrolidines via IMDAF: Experimental
 and Theoretical Investigation of the Observed Stereoselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7921
_journal_page_last               7927
_journal_paper_doi               10.1021/jo801138s
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H15 Cl3 N1 O5 P1'
_chemical_formula_sum            'C12 H15 Cl3 N O5 P'
_chemical_formula_weight         390.59
_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
_audit_creation_date             06-05-05
_audit_creation_method           CRYSTALS_ver_12.39
_cell_angle_alpha                90
_cell_angle_beta                 95.57(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7090(11)
_cell_length_b                   15.564(3)
_cell_length_c                   9.0050(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      18
_cell_measurement_theta_min      15
_cell_volume                     796.4(3)
_computing_cell_refinement       'Win AFC'
_computing_data_collection       'Win AFC'
_computing_data_reduction        'TeXsan 10.3b'
_computing_molecular_graphics    'CAMERON (Watkin et al 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1903
_diffrn_reflns_theta_full        27.488
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.272
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
; 
 Azimutal absorption correction (North et al, 1968) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.27
_refine_diff_density_min         -4.89
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0420
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1715
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000143
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 10.9 13.9 5.20 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1503
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1444
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              0
_reflns_limit_k_min              -20
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1715
_reflns_number_total             1889
_reflns_threshold_expression     I>3.00u(I)
_oxford_diffrn_Wilson_B_factor   3.35
_oxford_diffrn_Wilson_scale      4.57
_oxford_refine_ls_scale          0.548(3)
_oxford_structure_analysis_title 'new in P2(1)'
_cod_data_source_file            jo801138s_si_002.cif
_cod_data_source_block           CRYSTALS_cif
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C12 H15 Cl3 N1 O5 P1'
_cod_database_code               4023726