#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/16/4021626.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4021626
loop_
_publ_author_name
'Zhenfeng Xi'
'Zhiyi Song'
'Guangzhen Liu'
'Xiaozhong Liu'
'Tamotsu Takahashi'
_publ_section_title
;
 Preparation of Partially Substituted 1-Halo- and 1,4-Dihalo-1,3-dienes
 via Reagent-Controlled Desilylation of Halogenated 1,3-Dienes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3154
_journal_page_last               3158
_journal_paper_doi               10.1021/jo060003f
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C8 H10 I2'
_chemical_formula_weight         359.96
_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
;
    'hydrogen atoms are generated by HFIX
                                  instructions'
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 123.76(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.122(3)
_cell_length_b                   8.9810(18)
_cell_length_c                   10.755(2)
_cell_measurement_reflns_used    4028
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.94
_cell_volume                     1053.7(4)
_computing_cell_refinement
;
        'Molecular Structure Corporation (1994)
                                   MSC/AFC Diffractometer Control Software
                                   MSC, 3200 Research Forest Drive, The
                                   Woodlands, TX 77381 USA.'
;
_computing_data_collection
;
        'Molecular Structure Corporation (1994)
                                   MSC/AFC Diffractometer Control Software
                                   MSC, 3200 Research Forest Drive, The
                                   Woodlands, TX 77381, USA.'
;
_computing_data_reduction
;
         'Sheldrick, G. M. (1998) SHELXS98, Program
                                   for the Solution of Crystal Structure,
                                   University of Gottingen, Germany.'
;
_computing_molecular_graphics
;
     'Interactive Molecular Graphics XP, Virsion'
                                   4.2 for MSDOS (1990), Siemens Analytical
                                   X-ray Instruments Inc., Madison, Wisconsin,
                                   USA.'
;
_computing_publication_material
;
   'Sheldrick, G. M. (1998) SHELXL98, Program
                                   for the refinement of Crystal Structure,
                                   University of Gottingen, Germany.'
 
;
_computing_structure_refinement
;
   'Sheldrick, G. M. (1998) SHELXL98, Program
                                   for the Refinement of Crystal Structure,
                                   University of Gottingen, Germany.'
;
_computing_structure_solution
;
     'Sheldrick, G. M. (1998) SHELXS98, Program
                                   for the Solution of Crystal Structure,
                                   University of Gottingen, Germany.'
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_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  0.0775
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4028
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    5.906
_exptl_absorpt_correction_T_max  0.412
_exptl_absorpt_correction_T_min  0.116
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    2.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.241
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.095(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment
;
     'hydrogen coordinates ride on the coordinates
                                  of the previous atom, the isotropic U values
                                  are 1.2 OR 1.5 time over the U values of the
                                  previous atom.'
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0793P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                659
_reflns_number_total             1181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060003fsi20060103_030216.cif
_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.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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      'C 2/c'
_cod_database_code               4021626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.32292(5) 0.61949(7) 0.16190(8) 0.0989(6) Uani 1 1 d .
C1 C 0.4092(8) 0.4392(10) 0.3084(9) 0.071(2) Uani 1 1 d .
H1 H 0.3947 0.4266 0.3831 0.085 Uiso 1 1 calc R
C2 C 0.4823(7) 0.3422(8) 0.3034(8) 0.0567(17) Uani 1 1 d .
C3 C 0.5240(10) 0.2067(10) 0.3983(11) 0.084(3) Uani 1 1 d .
H3A H 0.4925 0.2082 0.4613 0.101 Uiso 1 1 calc R
H3B H 0.6128 0.2063 0.4628 0.101 Uiso 1 1 calc R
C4 C 0.4802(11) 0.0662(11) 0.3032(12) 0.092(3) Uani 1 1 d .
H4A H 0.5136 -0.0205 0.3675 0.111 Uiso 1 1 calc R
H4B H 0.3915 0.0606 0.2474 0.111 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0830(7) 0.0919(7) 0.1275(10) 0.0077(4) 0.0621(6) 0.0262(3)
C1 0.081(5) 0.088(5) 0.066(5) -0.027(4) 0.056(4) -0.021(4)
C2 0.056(4) 0.062(4) 0.060(5) -0.012(3) 0.037(4) -0.008(3)
C3 0.107(6) 0.078(6) 0.089(7) 0.004(5) 0.068(6) -0.008(5)
C4 0.119(8) 0.062(4) 0.113(8) -0.009(5) 0.075(6) -0.005(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 I1 125.5(6) . .
C1 C2 C2 126.1(7) . 2_655
C1 C2 C3 120.8(7) . .
C2 C2 C3 112.6(6) 2_655 .
C2 C3 C4 111.1(8) . .
C4 C4 C3 110.6(7) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.098(10) .
C1 C2 1.319(11) .
C2 C2 1.458(14) 2_655
C2 C3 1.484(12) .
C3 C4 1.521(13) .
C4 C4 1.496(18) 2_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
I1 C1 C2 C2 0.5(12) . 2_655
I1 C1 C2 C3 -171.1(6) . .
C1 C2 C3 C4 118.2(9) . .
C2 C2 C3 C4 -54.4(10) 2_655 .
C2 C3 C4 C4 55.0(12) . 2_655
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11717441
