#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222327.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_2222327
loop_
_publ_author_name
'McAdam, C. John'
'Hanton, Lyall R.'
'Moratti, Stephen C.'
'Simpson, Jim'
_publ_section_title
;
 1,4-Bis(iodomethyl)benzene
;
_journal_coeditor_code           HB2998
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1573
_journal_page_last               o1574
_journal_paper_doi               10.1107/S1600536809021151
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H8 I2'
_chemical_formula_moiety         'C8 H8 I2'
_chemical_formula_sum            'C8 H8 I2'
_chemical_formula_weight         357.94
_chemical_name_common            α,α'-diiodo-p-xylene
_chemical_name_systematic
;
1,4-bis(iodomethyl)benzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0978(3)
_cell_length_b                   4.5982(2)
_cell_length_c                   11.2793(3)
_cell_measurement_reflns_used    5590
_cell_measurement_temperature    89(2)
_cell_measurement_theta_max      33.03
_cell_measurement_theta_min      2.27
_cell_volume                     464.96(3)
_computing_cell_refinement       'APEX2 (Bruker 2006) and SAINT (Bruker 2006)'
_computing_data_collection       'APEX2 (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al.,
2004), PLATON (Spek, 2009)
and publCIF (Westrip, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson,
1999)
;
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_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    0.0183
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8198
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         33.41
_diffrn_reflns_theta_min         3.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.692
_exptl_absorpt_correction_T_max  0.818
_exptl_absorpt_correction_T_min  0.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    2.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.510
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0156
_refine_ls_R_factor_gt           0.0134
_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/[σ²(Fo²)+(0.0145P)²+0.1407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0320
_refine_ls_wR_factor_ref         0.0327
_reflns_number_gt                1538
_reflns_number_total             1674
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2998.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222327
_cod_database_fobs_code          2222327
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.62504(16) 0.1521(3) 0.47504(13) 0.0138(2) Uani d . 1 . .
C C2 0.63784(17) -0.0405(3) 0.57245(14) 0.0154(3) Uani d . 1 . .
C C3 0.51429(17) -0.1903(3) 0.59710(14) 0.0154(3) Uani d . 1 . .
C C4 0.75717(18) 0.3189(4) 0.45106(15) 0.0190(3) Uani d . 1 . .
I I1 0.880515(9) 0.07951(2) 0.331669(8) 0.01438(4) Uani d . 1 . .
H H2 0.729(3) -0.073(4) 0.620(2) 0.021(6) Uiso d . 1 . .
H H41 0.841(3) 0.354(5) 0.524(2) 0.031(6) Uiso d . 1 . .
H H3 0.523(2) -0.330(5) 0.6678(19) 0.022(5) Uiso d . 1 . .
H H42 0.733(3) 0.509(5) 0.405(2) 0.021(5) Uiso d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0142(6) 0.0109(6) 0.0180(6) -0.0017(5) 0.0078(5) -0.0032(5)
C2 0.0133(6) 0.0159(7) 0.0174(7) 0.0007(5) 0.0038(5) -0.0010(5)
C3 0.0175(6) 0.0126(6) 0.0175(6) 0.0006(5) 0.0070(5) 0.0012(5)
C4 0.0191(7) 0.0150(7) 0.0258(8) -0.0039(5) 0.0124(6) -0.0051(6)
I1 0.01367(5) 0.01628(6) 0.01473(5) -0.00037(3) 0.00680(3) 0.00092(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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C1 C2 3_656 . 118.88(13) ?
C3 C1 C4 3_656 . 120.68(14) ?
C2 C1 C4 . . 120.42(14) ?
C3 C2 C1 . . 120.64(14) ?
C3 C2 H2 . . 119.1(14) ?
C1 C2 H2 . . 120.3(14) ?
C2 C3 C1 . 3_656 120.48(14) ?
C2 C3 H3 . . 120.9(12) ?
C1 C3 H3 3_656 . 118.7(12) ?
C1 C4 I1 . . 111.52(10) ?
C1 C4 H41 . . 116.4(13) ?
I1 C4 H41 . . 100.5(13) ?
C1 C4 H42 . . 114.9(13) ?
I1 C4 H42 . . 101.8(13) ?
H41 C4 H42 . . 109.8(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C3 3_656 1.396(2) ?
C1 C2 . 1.401(2) ?
C1 C4 . 1.489(2) ?
C2 C3 . 1.386(2) ?
C2 H2 . 0.92(2) ?
C3 C1 3_656 1.396(2) ?
C3 H3 . 1.01(2) ?
C4 I1 . 2.1907(15) ?
C4 H41 . 1.04(2) ?
C4 H42 . 1.02(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H42 I1 1_565 1.02(2) 3.12(2) 3.9774(16) 141.8(16)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 C1 C2 C3 3_656 . . . -0.1(2) ?
C4 C1 C2 C3 . . . . 178.24(14) ?
C1 C2 C3 C1 . . . 3_656 0.1(2) ?
C3 C1 C4 I1 3_656 . . . -91.95(15) ?
C2 C1 C4 I1 . . . . 89.71(15) ?
