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_4028531
_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         'C15 H19 Cl2 N2 O5 P'
_chemical_formula_sum            'C15 H19 Cl2 N2 O5 P'
_chemical_formula_weight         409.19
_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             2013-03-28
_audit_creation_method
;
  Olex2 1.2
  (compiled Mar 21 2013 11:16:32, GUI svn.r4446)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 120.027(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0945(13)
_cell_length_b                   11.1936(9)
_cell_length_c                   21.398(3)
_cell_measurement_reflns_used    1405
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.8110
_cell_measurement_theta_min      4.6100
_cell_volume                     1886.0(5)
_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 0.9736
_diffrn_measured_fraction_theta_max 0.9736
_diffrn_measurement_details
;
  1 omega   -4.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       42.1798  -93.0000   86.0000 84

  2 omega  -50.00   25.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   93.0000  -86.0000 75

  3 omega  101.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   93.0000  -86.0000 77

  4 omega   26.00   90.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -93.0000  -18.0000 64

  5 omega   36.00   85.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -93.0000  -93.0000 49

  6 omega  105.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   93.0000 -161.0000 70

  7 omega   70.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       42.1798 -125.0000  -30.0000 25

  8 omega -121.00  -96.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -120.0000 25

  9 omega -125.00  -91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  -60.0000 34

 10 omega -116.00  -91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000    0.0000 25

 11 omega   44.00   69.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -30.0000 25

 12 omega   39.00   86.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  150.0000 47

 13 omega   44.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000 -150.0000 47

 14 omega   35.00   71.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  120.0000 36
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1325143000
_diffrn_orient_matrix_UB_12      0.1010277000
_diffrn_orient_matrix_UB_13      0.0244456000
_diffrn_orient_matrix_UB_21      0.1264336000
_diffrn_orient_matrix_UB_22      -0.0769829000
_diffrn_orient_matrix_UB_23      0.0643271000
_diffrn_orient_matrix_UB_31      0.0689145000
_diffrn_orient_matrix_UB_32      -0.0529516000
_diffrn_orient_matrix_UB_33      -0.0467224000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6793
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.62
_diffrn_source                   'SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    4.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41910
_exptl_absorpt_correction_type   multi-scan
_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)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       rod
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.1324
_exptl_crystal_size_mid          0.0816
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0702
_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^)+(0.1044P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.2166
_reflns_number_gt                1903
_reflns_number_total             3245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401185u_si_002.cif
_cod_data_source_block           cs005
_cod_database_code               4028531
_chemical_oxdiff_formula         'C15 H19 Cl2 N2 O5 P'
_reflns_odcompleteness_completeness 97.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C14A = O2-C14B
 1.45 with sigma of 0.01
 C14A-C15A = C14B-C15B
 1.49 with sigma of 0.01
 O2-C15A = O2-C15B
 2.38 with sigma of 0.02
3. others
 Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=1-
 Sof(H14A)=1-Sof(H14A)=1-Sof(H14A)=1-Sof(H14A)=1-Sof(H14A)=1-Sof(H14A)=1-
 Sof(H14A)
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B), C14A(H14A,H14B), C14B(H14C,H14D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15A(H15A,H15B,H15C), C15B(H15D,H15E,H15F)
;