#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:01:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180408 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/77/7207731.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_7207731
loop_
_publ_author_name
'Perkins, Catherine'
'Libri, Stefano'
'Adams, Harry'
'Brammer, Lee'
_publ_section_title
;
 Diiodoacetylene: compact, strong ditopic halogen bond donor
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3033
_journal_paper_doi               10.1039/c2ce00029f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C2 I4, C6 H12 N4'
_chemical_formula_sum            'C8 H12 I4 N4'
_chemical_formula_weight         671.82
_chemical_name_systematic
;
?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.800(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.9274(7)
_cell_length_b                   11.0145(4)
_cell_length_c                   8.7574(4)
_cell_measurement_temperature    120(2)
_cell_volume                     1534.50(11)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15754
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    8.106
_exptl_absorpt_correction_T_max  0.3081
_exptl_absorpt_correction_T_min  0.1282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.908
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_refine_diff_density_max         2.610
_refine_diff_density_min         -2.270
_refine_diff_density_rms         0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0491
_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)+(0.0122P)²+27.9266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                2595
_reflns_number_total             3358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce00029f.txt
_cod_data_source_block           hmta
_cod_database_code               7207731
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.90295(4) 0.83175(6) 0.89611(8) 0.02702(17) Uani 1 1 d . . .
I2 I 0.89769(4) 1.15564(6) 0.88433(8) 0.02817(17) Uani 1 1 d . . .
C8 C 0.9641(5) 0.9974(8) 0.9573(10) 0.0173(16) Uani 1 1 d . . .
I3 I 0.60412(3) 0.49898(6) 0.28517(7) 0.02528(15) Uani 1 1 d D . .
I4A I 0.52722(9) 0.72128(8) 0.54696(18) 0.0222(3) Uani 0.609(3) 1 d PDU A 1
I4B I 0.4918(9) 0.7274(2) 0.4802(16) 0.0243(6) Uani 0.154(8) 1 d PDU A 2
I4C I 0.4710(5) 0.7186(3) 0.4452(8) 0.0269(6) Uani 0.237(9) 1 d PDU A 3
C7 C 0.5220(4) 0.5400(6) 0.4627(7) 0.021(3) Uani 0.547(19) 1 d PDU . .
C7' C 0.4793(4) 0.5414(6) 0.5399(7) 0.021(3) Uani 0.453(19) 1 d PDU . .
N1 N 0.1979(5) 0.3969(8) 0.1444(11) 0.034(2) Uani 1 1 d . . .
N2 N 0.2050(5) 0.6177(8) 0.1570(11) 0.032(2) Uani 1 1 d . . .
N3 N 0.3000(5) 0.5066(8) -0.0058(9) 0.0250(17) Uani 1 1 d . . .
N4 N 0.3188(4) 0.4944(7) 0.2736(8) 0.0223(16) Uani 1 1 d . . .
C1 C 0.2504(7) 0.6195(11) 0.0146(13) 0.040(3) Uani 1 1 d . . .
H1A H 0.2887 0.6902 0.0159 0.048 Uiso 1 1 calc R . .
H1B H 0.2095 0.6291 -0.0733 0.048 Uiso 1 1 calc R . .
C2 C 0.2428(7) 0.4033(12) 0.0009(13) 0.041(3) Uani 1 1 d . . .
H2A H 0.2753 0.3275 -0.0106 0.050 Uiso 1 1 calc R . .
H2B H 0.2010 0.4083 -0.0863 0.050 Uiso 1 1 calc R . .
C3 C 0.1503(6) 0.5111(11) 0.1573(12) 0.036(3) Uani 1 1 d . . .
H3A H 0.1081 0.5170 0.0708 0.043 Uiso 1 1 calc R . .
H3B H 0.1198 0.5100 0.2532 0.043 Uiso 1 1 calc R . .
C4 C 0.2684(7) 0.6052(9) 0.2862(12) 0.029(2) Uani 1 1 d . . .
H4A H 0.3061 0.6767 0.2884 0.035 Uiso 1 1 calc R . .
H4B H 0.2393 0.6034 0.3836 0.035 Uiso 1 1 calc R . .
C5 C 0.2606(7) 0.3907(9) 0.2679(13) 0.031(2) Uani 1 1 d . . .
H5A H 0.2934 0.3150 0.2577 0.037 Uiso 1 1 calc R . .
H5B H 0.2322 0.3864 0.3658 0.037 Uiso 1 1 calc R . .
C6 C 0.3603(5) 0.4993(8) 0.1276(11) 0.0224(18) Uani 1 1 d . . .
H6A H 0.3956 0.4259 0.1179 0.027 Uiso 1 1 calc R . .
H6B H 0.3979 0.5709 0.1277 0.027 Uiso 1 1 calc R . .
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'
N N 0.0061 0.0033 '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
C8 C8 I1 123.2(9) 3_777 .
C8 C8 I2 122.3(9) 3_777 .
I1 C8 I2 114.4(4) . .
C7 C7 I4B 119.1(3) 3_666 .
C7 C7 I4A 117.9(2) 3_666 .
C7 C7 I3 125.5(3) 3_666 .
I4B C7 I3 114.0(4) . .
I4A C7 I3 115.9(4) . .
C7 C7 I4C 116.3(3) 3_666 .
I3 C7 I4C 112.9(4) . .
C7' C7' I4A 117.7(3) 3_666 .
C7' C7' I4C 116.4(3) 3_666 .
C7' C7' I4B 118.2(2) 3_666 .
C7' C7' I3 125.0(3) 3_666 3_666
I4A C7' I3 114.3(4) . 3_666
I4C C7' I3 116.4(4) . 3_666
I4B C7' I3 116.6(4) . 3_666
C5 N1 C3 108.9(8) . .
C5 N1 C2 107.1(8) . .
C3 N1 C2 107.2(9) . .
C3 N2 C1 109.3(9) . .
C3 N2 C4 107.9(8) . .
C1 N2 C4 107.7(8) . .
C2 N3 C6 108.0(8) . .
C2 N3 C1 108.1(8) . .
C6 N3 C1 106.2(8) . .
C5 N4 C6 108.0(7) . .
C5 N4 C4 107.6(7) . .
C6 N4 C4 107.8(7) . .
N2 C1 N3 112.1(8) . .
N2 C1 H1A 109.2 . .
N3 C1 H1A 109.2 . .
N2 C1 H1B 109.2 . .
N3 C1 H1B 109.2 . .
H1A C1 H1B 107.9 . .
N3 C2 N1 113.6(8) . .
N3 C2 H2A 108.9 . .
N1 C2 H2A 108.9 . .
N3 C2 H2B 108.9 . .
N1 C2 H2B 108.9 . .
H2A C2 H2B 107.7 . .
N2 C3 N1 112.0(7) . .
N2 C3 H3A 109.2 . .
N1 C3 H3A 109.2 . .
N2 C3 H3B 109.2 . .
N1 C3 H3B 109.2 . .
H3A C3 H3B 107.9 . .
N4 C4 N2 111.9(8) . .
N4 C4 H4A 109.2 . .
N2 C4 H4A 109.2 . .
N4 C4 H4B 109.2 . .
N2 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
N1 C5 N4 113.7(8) . .
N1 C5 H5A 108.8 . .
N4 C5 H5A 108.8 . .
N1 C5 H5B 108.8 . .
N4 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
N4 C6 N3 112.7(7) . .
N4 C6 H6A 109.0 . .
N3 C6 H6A 109.0 . .
N4 C6 H6B 109.0 . .
N3 C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C8 2.125(9) .
I2 C8 2.121(9) .
C8 C8 1.336(16) 3_777
I3 C7 2.129(5) .
I3 C7' 2.124(5) 3_666
I4A C7 2.129(5) .
I4A C7' 2.123(5) .
I4B C7 2.127(5) .
I4B C7' 2.126(5) .
I4C C7 2.131(5) .
I4C C7' 2.122(5) .
C7 C7 1.318(18) 3_666
C7' C7' 1.341(18) 3_666
C7' I3 2.124(5) 3_666
N1 C5 1.438(14) .
N1 C3 1.476(14) .
N1 C2 1.478(13) .
N2 C3 1.462(13) .
N2 C1 1.472(13) .
N2 C4 1.486(14) .
N3 C2 1.460(13) .
N3 C6 1.478(12) .
N3 C1 1.488(13) .
N4 C5 1.469(12) .
N4 C6 1.469(11) .
N4 C4 1.468(12) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
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
C3 N2 C1 N3 -57.2(12)
C4 N2 C1 N3 59.7(12)
C2 N3 C1 N2 55.9(12)
C6 N3 C1 N2 -59.8(11)
C6 N3 C2 N1 57.0(12)
C1 N3 C2 N1 -57.5(12)
C5 N1 C2 N3 -58.2(13)
C3 N1 C2 N3 58.6(12)
C1 N2 C3 N1 58.8(11)
C4 N2 C3 N1 -57.9(10)
C5 N1 C3 N2 57.3(11)
C2 N1 C3 N2 -58.3(11)
C5 N4 C4 N2 -57.9(10)
C6 N4 C4 N2 58.4(10)
C3 N2 C4 N4 59.1(10)
C1 N2 C4 N4 -58.7(11)
C3 N1 C5 N4 -57.2(10)
C2 N1 C5 N4 58.5(11)
C6 N4 C5 N1 -58.5(10)
C4 N4 C5 N1 57.6(10)
C5 N4 C6 N3 56.2(10)
C4 N4 C6 N3 -59.8(10)
C2 N3 C6 N4 -56.0(10)
C1 N3 C6 N4 59.8(10)
