#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/04/2210485.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210485
loop_
_publ_author_name
'Shaikh, Nadim S.'
'Swenson, Dale C.'
'Lehmler, Hans-J.'
_publ_section_title
;
 2,3,6-Trichloroiodobenzene
;
_journal_coeditor_code           AT2119
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4672
_journal_page_last               o4673
_journal_paper_doi               10.1107/S1600536806038426
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C6 H2 Cl3 I'
_chemical_formula_moiety         'C6 H2 Cl3 I'
_chemical_formula_sum            'C6 H2 Cl3 I'
_chemical_formula_weight         307.33
_chemical_name_common            2,3,6-Trichloroiodobenzene
_chemical_name_systematic
;
2,3,6-Trichloro-1-iodobenzene
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4873(16)
_cell_length_b                   4.0530(4)
_cell_length_c                   12.7746(13)
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     853.64(15)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20082
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.608
_exptl_absorpt_correction_T_max  0.8023
_exptl_absorpt_correction_T_min  0.4043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.496
_refine_ls_abs_structure_details 'Flack (1983), 924 Freidel pairs'
_refine_ls_abs_structure_Flack   0.30(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1946
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                1678
_reflns_number_total             1946
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            at2119.cif
_cod_data_source_block           I
_cod_database_code               2210485
_cod_database_fobs_code          2210485
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6506(8) 0.145(2) 0.5776(9) 0.0384(16) Uani d PD 0.625(5) A 1
I I1 0.60838(9) -0.0672(2) 0.7202(2) 0.0550(3) Uani d PD 0.625(5) A 1
C C2 0.5952(7) 0.268(2) 0.5039(10) 0.0402(17) Uani d PD 0.625(5) A 1
Cl Cl2 0.4935(7) 0.2459(15) 0.5292(9) 0.0627(8) Uani d PD 0.625(5) A 1
C C3 0.6232(7) 0.415(2) 0.4143(9) 0.0367(17) Uani d PD 0.625(5) A 1
Cl Cl3 0.5587(3) 0.5682(10) 0.3206(4) 0.0490(9) Uani d PD 0.625(5) A 1
C C4 0.7074(7) 0.440(2) 0.3947(8) 0.0366(18) Uani d PD 0.625(5) A 1
H H4 0.7266 0.5433 0.3326 0.044 Uiso calc PR 0.625(5) A 1
C C5 0.7601(7) 0.317(2) 0.4652(9) 0.0411(18) Uani d PD 0.625(5) A 1
H H5 0.8166 0.3286 0.4514 0.049 Uiso calc PR 0.625(5) A 1
C C6 0.7333(8) 0.174(2) 0.5576(9) 0.0397(17) Uani d PD 0.625(5) A 1
Cl Cl6 0.8023(4) 0.0157(14) 0.6448(6) 0.0522(7) Uani d PD 0.625(5) A 1
C C1' 0.6090(8) 0.253(3) 0.5145(12) 0.0402(17) Uani d PD 0.339(3) B 2
I I1' 0.4810(3) 0.2064(7) 0.5342(5) 0.0627(8) Uani d PD 0.339(3) B 2
C C2' 0.6628(9) 0.129(3) 0.5896(11) 0.0384(16) Uani d PD 0.339(3) B 2
Cl Cl2' 0.6263(7) -0.043(2) 0.7022(8) 0.0550(3) Uani d PD 0.339(3) B 2
C C3' 0.7449(9) 0.151(3) 0.5729(11) 0.0397(17) Uani d PD 0.339(3) B 2
Cl Cl3' 0.8139(7) 0.000(3) 0.6614(10) 0.0522(7) Uani d PD 0.339(3) B 2
C C4' 0.7759(7) 0.294(3) 0.4803(11) 0.0411(18) Uani d PD 0.339(3) B 2
H H4' 0.8328 0.3052 0.4686 0.049 Uiso calc PR 0.339(3) B 2
C C5' 0.7237(8) 0.415(3) 0.4090(11) 0.0366(18) Uani d PD 0.339(3) B 2
H H5' 0.7443 0.5142 0.3471 0.044 Uiso calc PR 0.339(3) B 2
C C6' 0.6407(8) 0.397(3) 0.4242(11) 0.0367(17) Uani d PD 0.339(3) B 2
Cl Cl6' 0.5761(7) 0.563(2) 0.3329(8) 0.0490(9) Uani d PD 0.339(3) B 2
C C1" 0.6365(19) 0.126(4) 0.5961(17) 0.0384(16) Uani d PD 0.036(3) C 3
I I1" 0.599(2) -0.093(4) 0.7399(15) 0.0550(3) Uani d PD 0.036(3) C 3
C C2" 0.7192(19) 0.156(4) 0.5716(18) 0.0397(17) Uani d PD 0.036(3) C 3
Cl Cl2" 0.7904(19) 0.013(4) 0.657(2) 0.0522(7) Uani d PD 0.036(3) C 3
C C3" 0.7420(19) 0.300(4) 0.4790(18) 0.0411(18) Uani d PD 0.036(3) C 3
Cl Cl3" 0.8420(19) 0.345(5) 0.444(2) 0.049 Uiso d PD 0.036(3) C 3
C C4" 0.683(2) 0.418(4) 0.4077(17) 0.0366(18) Uani d PD 0.036(3) C 3
H H4" 0.6992 0.5177 0.3437 0.044 Uiso calc PR 0.036(3) C 3
C C5" 0.604(2) 0.388(4) 0.4319(17) 0.0367(17) Uani d PD 0.036(3) C 3
H H5" 0.5643 0.4672 0.3843 0.044 Uiso calc PR 0.036(3) C 3
C C6" 0.5794(19) 0.244(4) 0.5250(17) 0.0402(17) Uani d PD 0.036(3) C 3
Cl Cl6" 0.4779(18) 0.209(4) 0.5529(18) 0.0627(8) Uani d PD 0.036(3) C 3
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C6 C1 C2 118.9(13) yes
C6 C1 I1 120.8(8) yes
C2 C1 I1 120.3(12) yes
C3 C2 C1 119.7(13) yes
C3 C2 Cl2 120.8(10) yes
C1 C2 Cl2 119.5(13) yes
C2 C3 C4 120.7(9) yes
C2 C3 Cl3 122.0(9) yes
C4 C3 Cl3 117.3(9) yes
C5 C4 C3 119.2(12) yes
C5 C4 H4 120.4 ?
C3 C4 H4 120.4 ?
C4 C5 C6 121.2(12) yes
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C5 C6 C1 120.3(9) yes
C5 C6 Cl6 119.8(9) yes
C1 C6 Cl6 119.8(9) yes
C6' C1' C2' 118.7(13) ?
C6' C1' I1' 120.3(9) ?
C2' C1' I1' 120.9(13) ?
C3' C2' C1' 119.7(14) ?
C3' C2' Cl2' 120.3(10) ?
C1' C2' Cl2' 120.0(14) ?
C2' C3' C4' 120.8(10) ?
C2' C3' Cl3' 121.9(10) ?
C4' C3' Cl3' 117.3(10) ?
C5' C4' C3' 119.0(13) ?
C5' C4' H4' 120.5 ?
C3' C4' H4' 120.5 ?
C4' C5' C6' 121.3(13) ?
C4' C5' H5' 119.4 ?
C6' C5' H5' 119.4 ?
C5' C6' C1' 120.5(10) ?
C5' C6' Cl6' 119.9(10) ?
C1' C6' Cl6' 119.6(10) ?
C6" C1" C2" 118.8(13) ?
C6" C1" I1" 120.5(9) ?
C2" C1" I1" 120.7(13) ?
C3" C2" C1" 119.7(14) ?
C3" C2" Cl2" 120.6(10) ?
C1" C2" Cl2" 119.7(14) ?
C2" C3" C4" 120.7(10) ?
C2" C3" Cl3" 122.1(10) ?
C4" C3" Cl3" 117.2(10) ?
C5" C4" C3" 119.1(13) ?
C5" C4" H4" 120.4 ?
C3" C4" H4" 120.4 ?
C4" C5" C6" 121.3(13) ?
C4" C5" H5" 119.4 ?
C6" C5" H5" 119.4 ?
C5" C6" C1" 120.4(10) ?
C5" C6" Cl6" 119.9(10) ?
C1" C6" Cl6" 119.7(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.392(18) yes
C1 C2 1.405(9) yes
C1 I1 2.131(12) yes
C2 C3 1.370(18) yes
C2 Cl2 1.710(15) yes
C3 C4 1.414(16) yes
C3 Cl3 1.718(10) yes
C4 C5 1.346(9) yes
C4 H4 0.9500 ?
C5 C6 1.387(16) yes
C5 H5 0.9500 ?
C6 Cl6 1.719(11) yes
C1' C6' 1.394(19) ?
C1' C2' 1.401(9) ?
C1' I1' 2.133(13) ?
C2' C3' 1.373(19) ?
C2' Cl2' 1.709(15) ?
C3' C4' 1.414(17) ?
C3' Cl3' 1.716(11) ?
C4' C5' 1.345(10) ?
C4' H4' 0.9500 ?
C5' C6' 1.385(17) ?
C5' H5' 0.9500 ?
C6' Cl6' 1.715(11) ?
C1" C6" 1.393(19) ?
C1" C2" 1.403(9) ?
C1" I1" 2.132(13) ?
C2" C3" 1.372(18) ?
C2" Cl2" 1.709(16) ?
C3" C4" 1.415(16) ?
C3" Cl3" 1.718(11) ?
C4" C5" 1.345(10) ?
C4" H4" 0.9500 ?
C5" C6" 1.386(16) ?
C5" H5" 0.9500 ?
C6" Cl6" 1.717(11) ?
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
C6 C1 C2 C3 -0.1(12)
I1 C1 C2 C3 177.6(6)
C6 C1 C2 Cl2 -177.9(6)
I1 C1 C2 Cl2 -0.2(9)
C1 C2 C3 C4 0.6(12)
Cl2 C2 C3 C4 178.4(6)
C1 C2 C3 Cl3 179.5(6)
Cl2 C2 C3 Cl3 -2.7(10)
C2 C3 C4 C5 0.3(12)
Cl3 C3 C4 C5 -178.7(6)
C3 C4 C5 C6 -1.7(12)
C4 C5 C6 C1 2.3(12)
C4 C5 C6 Cl6 179.2(7)
C2 C1 C6 C5 -1.4(12)
I1 C1 C6 C5 -179.0(6)
C2 C1 C6 Cl6 -178.3(6)
I1 C1 C6 Cl6 4.1(9)
C6' C1' C2' C3' 0.0(17)
I1' C1' C2' C3' 177.3(9)
C6' C1' C2' Cl2' 179.0(9)
I1' C1' C2' Cl2' -3.6(14)
C1' C2' C3' C4' -0.6(17)
Cl2' C2' C3' C4' -179.7(9)
C1' C2' C3' Cl3' -179.4(10)
Cl2' C2' C3' Cl3' 1.5(15)
C2' C3' C4' C5' 1.1(17)
Cl3' C3' C4' C5' 179.9(10)
C3' C4' C5' C6' -0.8(17)
C4' C5' C6' C1' 0.2(18)
C4' C5' C6' Cl6' 178.4(10)
C2' C1' C6' C5' 0.3(17)
I1' C1' C6' C5' -177.1(9)
C2' C1' C6' Cl6' -178.0(9)
I1' C1' C6' Cl6' 4.6(14)
C6" C1" C2" C3" 0.0(18)
I1" C1" C2" C3" -179.5(10)
C6" C1" C2" Cl2" -179.9(11)
I1" C1" C2" Cl2" 0.5(16)
C1" C2" C3" C4" 0.1(19)
Cl2" C2" C3" C4" 180.0(11)
C1" C2" C3" Cl3" 179.8(11)
Cl2" C2" C3" Cl3" -0.3(17)
C2" C3" C4" C5" -0.1(19)
Cl3" C3" C4" C5" -179.8(11)
C3" C4" C5" C6" 0.0(19)
C4" C5" C6" C1" 0.0(19)
C4" C5" C6" Cl6" -179.8(11)
C2" C1" C6" C5" 0.0(18)
I1" C1" C6" C5" 179.5(10)
C2" C1" C6" Cl6" 179.8(11)
I1" C1" C6" Cl6" -0.7(16)
