Preparation, X-ray Structure, and Oxidative Reactivity of N-(2-Iodylphenyl)tosylamides and 2-Iodylphenyl Tosylate: Iodylarenes Stabilized by Ortho-Substitution with a Sulfonyl Group
Artur K. Mailyan; Ivan M. Geraskin; Victor N. Nemykin; Viktor V. Zhdankin; Journal of Organic Chemistry 74 (2009) 8444–8447; doi:10.1021/jo901638f

data_4024955
_publ_section_title
;
Preparation, X-ray Structure, and Oxidative Reactivity
of N-(2-Iodylphenyl)tosylamides and 2-Iodylphenyl Tosylate: Iodylarenes
Stabilized by Ortho-Substitution with a Sulfonyl Group
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8444
_journal_page_last               8447
_journal_paper_doi               10.1021/jo901638f
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C14 H14 I1 N1 O4 S1'
_chemical_formula_sum            'C14 H14 I N O4 S'
_chemical_formula_weight         419.24
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-03-03
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 117.351(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.253(3)
_cell_length_b                   8.3071(11)
_cell_length_c                   16.289(2)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    173
_cell_measurement_theta_max      18
_cell_measurement_theta_min      15
_cell_volume                     3035.1(7)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Unknown
_diffrn_measurement_device_type  Serial
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17627
_diffrn_reflns_theta_full        27.509
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         1.816
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  5
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.262
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.000706
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 16.0 16.3 8.09 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0492
_refine_ls_wR_factor_gt          0.0405
_refine_ls_wR_factor_ref         0.0376
_reflns_limit_h_max              29
_reflns_limit_h_min              -32
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2478
_reflns_number_total             3483
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.25
_oxford_diffrn_Wilson_scale      26.67
_oxford_refine_ls_r_factor_ref   0.0205
_oxford_refine_ls_scale          0.19584(5)
_oxford_reflns_number_all        3470
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_oxford_structure_analysis_title '08178a in C2/c'
_cod_data_source_file            jo901638f_si_001.cif
_cod_data_source_block           1
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_sum        'C14 H14 I1 N1 O4 S1'
_cod_database_code               4024955