#------------------------------------------------------------------------------
#$Date: 2015-11-19 04:01:29 +0200 (Thu, 19 Nov 2015) $
#$Revision: 170403 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/13/2241324.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_2241324
loop_
_publ_author_name
'McAdam, C. John'
'Hanton, Lyall R.'
'Moratti, Stephen C.'
'Simpson, Jim'
_publ_section_title
;
 Crystal structures of two bis(iodomethyl)benzene derivatives:
 similarities and differences in the crystal packing
;
_journal_coeditor_code           SU5235
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1505
_journal_page_last               1509
_journal_paper_doi               10.1107/S2056989015021295
_journal_volume                  71
_journal_year                    2015
_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_systematic
;
1,2-Bis(iodomethyl)benzene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.637(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5485(5)
_cell_length_b                   8.0461(3)
_cell_length_c                   8.0582(3)
_cell_measurement_reflns_used    5091
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      32.87
_cell_measurement_theta_min      2.58
_cell_volume                     923.89(6)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al.,
2004),
PLATON (Spek, 2009),  publCIF (Westrip, 2010) and WinGX
(Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b) and TITAN2000 (Hunter & Simpson,
1999)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8422
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.410
_diffrn_reflns_theta_min         2.859
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.735
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.534104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.523
_refine_diff_density_min         -1.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         1667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0183
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0175P)²+1.2212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0438
_refine_ls_wR_factor_ref         0.0444
_reflns_number_gt                1552
_reflns_number_total             1667
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5235sup1.cif
_cod_data_source_block           I
_cod_database_code               2241324
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.229
_shelx_estimated_absorpt_t_max   0.432
loop_
_space_group_symop_operation_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_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_occupancy
I I1 0.31503(2) 0.11885(2) 0.75250(2) 0.01529(5) Uani d 1
C C11 0.41526(13) 0.2215(2) 0.6102(3) 0.0142(3) Uani d 1
H H111 0.4651 0.1386 0.6070 0.017 Uiso calc 1
H H112 0.3826 0.2433 0.4921 0.017 Uiso calc 1
C C1 0.45886(13) 0.3782(2) 0.6864(2) 0.0111(3) Uani d 1
C C2 0.41839(13) 0.5301(2) 0.6268(3) 0.0136(3) Uani d 1
H H2 0.3623 0.5307 0.5427 0.016 Uiso calc 1
C C3 0.45882(14) 0.6802(2) 0.6886(3) 0.0156(4) Uani d 1
H H3 0.4304 0.7823 0.6470 0.019 Uiso calc 1
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
C1 C11 I1 . . 112.15(13)
C1 C11 H111 . . 109.2
I1 C11 H111 . . 109.2
C1 C11 H112 . . 109.2
I1 C11 H112 . . 109.2
H111 C11 H112 . . 107.9
C2 C1 C1 . 2_656 119.10(11)
C2 C1 C11 . . 118.94(18)
C1 C1 C11 2_656 . 121.93(11)
C3 C2 C1 . . 121.16(18)
C3 C2 H2 . . 119.4
C1 C2 H2 . . 119.4
C2 C3 C3 . 2_656 119.72(12)
C2 C3 H3 . . 120.1
C3 C3 H3 2_656 . 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C11 . 2.1902(19)
C11 C1 . 1.487(3)
C11 H111 . 0.9900
C11 H112 . 0.9900
C1 C2 . 1.399(3)
C1 C1 2_656 1.410(4)
C2 C3 . 1.391(3)
C2 H2 . 0.9500
C3 C3 2_656 1.392(4)
C3 H3 . 0.9500
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
C3 H3 I1 6_565 0.95 3.38 4.046(2) 129
C11 H112 I1 7_556 0.99 3.33 4.179(2) 145
C2 H2 I1 7_556 0.95 3.36 4.257(2) 158
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_4
_geom_torsion
I1 C11 C1 C2 . . -93.41(19)
I1 C11 C1 C1 . 2_656 88.3(2)
C1 C1 C2 C3 2_656 . 1.2(3)
C11 C1 C2 C3 . . -177.12(17)
C1 C2 C3 C3 . 2_656 0.2(3)

_cod_database_fobs_code 2241324
