The Staudinger reaction with 2-imino-1,3-thiaselenanes toward the synthesis of C4 spiro-β-lactams.
Toyoda, Yosuke; Ninomiya, Masayuki; Ebihara, Masahiro; Koketsu, Mamoru; Organic & biomolecular chemistry 11 (2013) 2652–2659; doi:10.1039/c3ob00073g

data_7152845
_publ_section_title
;
 The Staudinger reaction with 2-imino-1,3-thiaselenanes toward the
 synthesis of C4 spiro-\b-lactams.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2652
_journal_page_last               2659
_journal_paper_doi               10.1039/c3ob00073g
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C11 H13 N S Se'
_chemical_formula_sum            'C11 H13 N S Se'
_chemical_formula_weight         270.24
_chemical_melting_point          62.5(5)
_chemical_name_systematic
;
2-(2-Methylphenylimino)-1,3-thiaselenane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.024(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.376(2)
_cell_length_b                   13.152(3)
_cell_length_c                   11.240(3)
_cell_measurement_reflns_used    3158
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4640
_cell_measurement_theta_min      3.0977
_cell_volume                     1201.3(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al.,2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR97
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC7R Mercury CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9484
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    3.261
_exptl_absorpt_correction_T_max  0.4755
_exptl_absorpt_correction_T_min  0.2841
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Higashi, 1999)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0240(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0509P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                1768
_reflns_number_total             2749
_reflns_threshold_expression     ' I>2\s(I)'
_cod_data_source_file            c3ob00073g.txt
_cod_data_source_block           6c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '62-63' was changed to '62.5(5)' -
the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'Numerical'
changed to 'numerical' 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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7152845