An Unusual Samarium Diiodide Mediated Reductive Ring Contraction of a Tricyclic Oxazine to a Highly-Functionalized Cyclopentane and Cyclobutane
McAuley, Barry J.; Nieuwenhuyzen, Mark; Sheldrake, Gary N.; Organic Letters 2 (2000) 1457–; doi:10.1021/ol000057q

data_1507546
_publ_section_title
;
 An Unusual Samarium Diiodide Mediated Reductive Ring Contraction of a
 Tricyclic Oxazine to a Highly-Functionalized Cyclopentane and Cyclobutane
;
_journal_issue                   10
_journal_name_full               'Organic Letters'
_journal_page_first              1457
_journal_paper_doi               10.1021/ol000057q
_journal_volume                  2
_journal_year                    2000
_chemical_formula_sum            'C17 H21 N O4'
_chemical_formula_weight         303.35
_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                 104.10(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.335(9)
_cell_length_b                   5.240(8)
_cell_length_c                   13.442(10)
_cell_measurement_temperature    153(2)
_cell_volume                     774.3(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.487
_diffrn_measured_fraction_theta_max 0.487
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_sigmaI/netI    0.1248
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1329
_diffrn_reflns_theta_full        30.36
_diffrn_reflns_theta_max         30.36
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1249
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                759
_reflns_number_total             1249
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol000057q_s2.cif
_cod_data_source_block           bmarp
_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1507546