Synthesis of Five- and Six-Membered Dihalogenated Heterocyclic Compounds by Electrophile-Triggered Cyclization
Ke-Gong Ji; Hai-Tao Zhu; Fang Yang; Ali Shaukat; Xiao-Feng Xia; Yan-Fang Yang; Xue-Yuan Liu; Yong-Min Liang; Journal of Organic Chemistry 75 (2010) 5670–5678; doi:10.1021/jo101085f

data_4025607
_publ_section_title
;
 Synthesis of Five- and Six-Membered Dihalogenated Heterocyclic Compounds
 by Electrophile-Triggered Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5670
_journal_page_last               5678
_journal_paper_doi               10.1021/jo101085f
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C16 H10 I2'
_chemical_formula_weight         456.04
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.687(3)
_cell_angle_beta                 77.515(4)
_cell_angle_gamma                85.659(3)
_cell_formula_units_Z            4
_cell_length_a                   9.1655(16)
_cell_length_b                   12.387(2)
_cell_length_c                   13.582(3)
_cell_measurement_reflns_used    3532
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.55
_cell_volume                     1464.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8153
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    4.274
_exptl_absorpt_correction_T_max  0.3328
_exptl_absorpt_correction_T_min  0.2935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         1.506
_refine_diff_density_min         -1.452
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0544P)^2^+4.3766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                4298
_reflns_number_total             5648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101085f_si_003.cif
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1464.6(5)
_cod_database_code               4025607