Highly regio- and stereoselective four-component iodoamination of Se-substituted allenes. an efficient synthesis of N-(3-organoseleno-2-iodo-2(Z)-propenyl) acetamides
Ma, Shengming; Hao, Xueshi; Huang, Xian; Chemical Communications (Cambridge, United Kingdom)  (2003) 1082–1083; doi:10.1039/b300879g

data_7113874
_publ_section_title
;
 Highly regio- and stereoselective four-component iodoamination of
 Se-substituted allenes. an efficient synthesis of
 N-(3-organoseleno-2-iodo-2(Z)-propenyl) acetamides
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   9
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1082
_journal_page_last               1083
_journal_paper_doi               10.1039/b300879g
_journal_year                    2003
_chemical_formula_sum            'C11 H12 I N O Se'
_chemical_formula_weight         380.08
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.263(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9005(10)
_cell_length_b                   13.2791(12)
_cell_length_c                   9.8573(9)
_cell_measurement_reflns_used    2160
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.733
_cell_measurement_theta_min      5.120
_cell_volume                     1300.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0738
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7761
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    5.236
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5625
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.164
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.827
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.064
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                1845
_reflns_number_total             3019
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7104095
_cod_data_source_file            b300879g.txt
_cod_data_source_block           cd21142
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C11 H12  N O Se I'
_cod_database_code               7113874