Novel Formation of Iodobenzene Derivatives from 1-(Methylthio)-3-tosylhexa-1,3-dien-5-ynes via Iodine-Induced Intramolecular Cyclization
Shoji Matsumoto; Kenji Takase; Katsuyuki Ogura; Journal of Organic Chemistry 73 (2008) 1726–1731; doi:10.1021/jo701976q

data_4023299
_publ_section_title
;
 Novel Formation of Iodobenzene Derivatives from
 1-(Methylthio)-3-tosylhexa-1,3-dien-5-ynes via Iodine-Induced
 Intramolecular Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1726
_journal_page_last               1731
_journal_paper_doi               10.1021/jo701976q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C19 H15 I O2 S'
_chemical_formula_weight         434.27
_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                 91.2310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9301(6)
_cell_length_b                   9.0295(5)
_cell_length_c                   15.9998(8)
_cell_measurement_reflns_used    6376
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.55
_cell_volume                     1723.15(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.906
_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  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9466
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_T_max  0.7549
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0022(2)
_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   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0185
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0219P)^2^+0.9827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0476
_reflns_number_gt                3676
_reflns_number_total             3967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701976q-File001.cif
_cod_data_source_block           akaz088p21n
_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_H-M      'P 21/n'
_cod_database_code               4023299