#------------------------------------------------------------------------------
#$Date: 2015-11-19 04:01:29 +0200 (Thu, 19 Nov 2015) $
#$Revision: 170403 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/13/2241325.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_2241325
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
;
1,3-Bis(iodomethyl)benzene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.2030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5323(3)
_cell_length_b                   4.54640(10)
_cell_length_c                   15.6269(4)
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      32.97
_cell_measurement_theta_min      2.62
_cell_volume                     957.46(4)
_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  0.0332
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.440
_diffrn_reflns_theta_min         3.023
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.499
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.569306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.237
_refine_diff_density_min         -0.767
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0239
_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)+(0.0109P)²+1.4343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0445
_refine_ls_wR_factor_ref         0.0477
_reflns_number_gt                2826
_reflns_number_total             3435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5235sup1.cif
_cod_data_source_block           II
_cod_database_code               2241325
_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   0.158
_shelx_estimated_absorpt_t_max   0.737
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.35561(2) 0.36401(4) 0.46514(2) 0.01445(4) Uani d 1
C C11 0.4498(2) 0.1469(6) 0.37746(17) 0.0197(5) Uani d 1
H H11A 0.5193 0.1461 0.4034 0.024 Uiso calc 1
H H11B 0.4282 -0.0599 0.3690 0.024 Uiso calc 1
C C1 0.44471(19) 0.2984(6) 0.29275(16) 0.0152(5) Uani d 1
C C2 0.51858(18) 0.4993(5) 0.27547(16) 0.0138(5) Uani d 1
H H2 0.5707 0.5419 0.3185 0.017 Uiso calc 1
C C3 0.51650(18) 0.6379(5) 0.19574(16) 0.0128(4) Uani d 1
C C31 0.59593(19) 0.8514(6) 0.17788(17) 0.0175(5) Uani d 1
H H31A 0.6261 0.9352 0.2326 0.021 Uiso calc 1
H H31B 0.5667 1.0148 0.1421 0.021 Uiso calc 1
I I3 0.71036(2) 0.63230(4) 0.11079(2) 0.01692(5) Uani d 1
C C4 0.43920(19) 0.5755(6) 0.13244(16) 0.0171(5) Uani d 1
H H4 0.4369 0.6696 0.0780 0.021 Uiso calc 1
C C5 0.36591(19) 0.3753(6) 0.14961(17) 0.0179(5) Uani d 1
H H5 0.3138 0.3322 0.1066 0.022 Uiso calc 1
C C6 0.36832(19) 0.2379(6) 0.22919(18) 0.0178(5) Uani d 1
H H6 0.3177 0.1021 0.2404 0.021 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_3
_geom_angle
C11 I1 I3 4_566 117.47(7)
C1 C11 I1 . 111.45(17)
C1 C11 H11A . 109.3
I1 C11 H11A . 109.3
C1 C11 H11B . 109.3
I1 C11 H11B . 109.3
H11A C11 H11B . 108.0
C6 C1 C2 . 119.2(2)
C6 C1 C11 . 120.9(2)
C2 C1 C11 . 119.9(2)
C3 C2 C1 . 120.7(2)
C3 C2 H2 . 119.6
C1 C2 H2 . 119.6
C2 C3 C4 . 119.5(2)
C2 C3 C31 . 120.3(2)
C4 C3 C31 . 120.2(2)
C3 C31 I3 . 110.27(16)
C3 C31 H31A . 109.6
I3 C31 H31A . 109.6
C3 C31 H31B . 109.6
I3 C31 H31B . 109.6
H31A C31 H31B . 108.1
C5 C4 C3 . 119.7(2)
C5 C4 H4 . 120.1
C3 C4 H4 . 120.1
C6 C5 C4 . 120.5(2)
C6 C5 H5 . 119.7
C4 C5 H5 . 119.7
C5 C6 C1 . 120.3(2)
C5 C6 H6 . 119.9
C1 C6 H6 . 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C11 . 2.189(3)
I1 I3 4_566 3.8662(2)
C11 C1 . 1.488(4)
C11 H11A . 0.9900
C11 H11B . 0.9900
C1 C6 . 1.394(4)
C1 C2 . 1.399(3)
C2 C3 . 1.394(3)
C2 H2 . 0.9500
C3 C4 . 1.402(3)
C3 C31 . 1.493(3)
C31 I3 . 2.187(2)
C31 H31A . 0.9900
C31 H31B . 0.9900
C4 C5 . 1.390(4)
C4 H4 . 0.9500
C5 C6 . 1.390(4)
C5 H5 . 0.9500
C6 H6 . 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
C11 H11B I1 1_545 0.99 3.22 4.060(3) 144
C5 H5 I1 2_545 0.95 3.25 4.078(3) 147
C31 H31A I3 2_655 0.99 3.27 4.224(3) 162
C31 H31A Cg 1_565 0.99 2.84 3.453(3) 121
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
I1 C11 C1 C6 -83.6(3)
I1 C11 C1 C2 97.9(2)
C6 C1 C2 C3 -0.1(4)
C11 C1 C2 C3 178.4(2)
C1 C2 C3 C4 0.2(4)
C1 C2 C3 C31 -179.8(2)
C2 C3 C31 I3 96.4(2)
C4 C3 C31 I3 -83.7(3)
C2 C3 C4 C5 -0.3(4)
C31 C3 C4 C5 179.7(2)
C3 C4 C5 C6 0.4(4)
C4 C5 C6 C1 -0.3(4)
C2 C1 C6 C5 0.2(4)
C11 C1 C6 C5 -178.4(2)

_cod_database_fobs_code 2241325
