Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes
Wouter Debrouwer; Thomas S. A. Heugebaert; Kristof Van Hecke; Christian V. Stevens; Journal of Organic Chemistry 78 (2013) 8232–8241; doi:10.1021/jo401185u

data_4028532
_publ_contact_author_address
;SynBioC Research Group,
Department of Sustainable Organic Chemistry and Technology,
Faculty of Bioscience Engineering,
Ghent University,
Coupure links 653,
B-9000 Gent,
Belgium    
;
_publ_contact_author_email       chris.stevens@ugent.be
_publ_contact_author_name        'Prof. Christian V. Stevens'
_publ_section_title
;
 Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8232
_journal_page_last               8241
_journal_paper_doi               10.1021/jo401185u
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C16 H19 Cl2 N2 O3 P'
_chemical_formula_sum            'C16 H19 Cl2 N2 O3 P'
_chemical_formula_weight         389.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-27
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.092(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6158(4)
_cell_length_b                   11.3767(5)
_cell_length_c                   17.5776(7)
_cell_measurement_reflns_used    2287
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.5360
_cell_measurement_theta_min      4.6300
_cell_volume                     1903.77(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_details
;
  1 omega  -91.00  -59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000 -156.0000  -50.0000 32

  2 omega  -69.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  120.0000   74.0000 64

  3 omega   37.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -120.0000  105.0000 48

  4 omega   97.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  120.0000   74.0000 79

  5 omega   78.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -156.0000 -166.0000 49

  6 omega   98.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  120.0000   10.0000 52

  7 omega    1.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -99.0000   30.0000 82

  8 omega  -55.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   45.0000    0.0000 85

  9 omega -125.00  -92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  -60.0000 33

 10 omega   95.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   60.0000 40

 11 omega   50.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000  -90.0000 68

 12 omega  142.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   60.0000 29

 13 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   30.0000 53

 14 omega   34.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -30.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0873694000
_diffrn_orient_matrix_UB_12      0.1138928000
_diffrn_orient_matrix_UB_13      0.0089539000
_diffrn_orient_matrix_UB_21      -0.1306666000
_diffrn_orient_matrix_UB_22      0.0714247000
_diffrn_orient_matrix_UB_23      -0.0335299000
_diffrn_orient_matrix_UB_31      -0.0385443000
_diffrn_orient_matrix_UB_32      0.0168476000
_diffrn_orient_matrix_UB_33      0.0813855000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7893
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.64
_diffrn_source                   'SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    4.007
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2058
_exptl_crystal_size_mid          0.1385
_exptl_crystal_size_min          0.0971
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.0057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                2323
_reflns_number_total             3369
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401185u_si_003.cif
_cod_data_source_block           cs003
_cod_original_cell_volume        1903.78(14)
_cod_database_code               4028532
_chemical_oxdiff_formula         'C15 H18 N2 O5 P1 Cl2'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97