Highly Regioselective Synthesis of 1,3-Diiodonaphthalene Derivatives via a Sequential Cascade Iodocyclization.
Wang, Li-Jing; Zhu, Hai-Tao; Lu, Lei; Yang, Fang; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 14 (2012) 1990–1993; doi:10.1021/ol300457c

data_1507587
_publ_section_title
;
 Highly Regioselective Synthesis of 1,3-Diiodonaphthalene Derivatives via
 a Sequential Cascade Iodocyclization.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1990
_journal_page_last               1993
_journal_paper_doi               10.1021/ol300457c
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C16 H10 I2'
_chemical_formula_weight         456.04
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.177(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.513(10)
_cell_length_b                   10.041(5)
_cell_length_c                   16.438(9)
_cell_measurement_reflns_used    3990
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.31
_cell_volume                     2915(3)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10195
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    4.295
_exptl_absorpt_correction_T_max  0.4517
_exptl_absorpt_correction_T_min  0.4131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.078
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.649
_refine_diff_density_min         -1.358
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0352P)^2^+9.9347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                2094
_reflns_number_total             2704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300457c_si_001.cif
_cod_data_source_block           c2c
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1507587