#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:40:08 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179591 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/56/4505682.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_4505682
loop_
_publ_author_name
'Crihfield, April'
'Hartwell, Joshua'
'Phelps, Dustin'
'Walsh, Rosa Bailey'
'Harris, Jeffery L.'
'Payne, John F.'
'Pennington, William T.'
'Hanks, Timothy W.'
_publ_section_title
;
 Crystal Engineering through Halogen Bonding. 2. Complexes of
 Diacetylene-Linked Heterocycles with Organic Iodides
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              313
_journal_paper_doi               10.1021/cg0340042
_journal_volume                  3
_journal_year                    2003
_chemical_formula_sum            'C24 H12 I4 N2'
_chemical_formula_weight         835.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.699(5)
_cell_angle_beta                 108.631(5)
_cell_angle_gamma                91.813(6)
_cell_formula_units_Z            1
_cell_length_a                   7.1360(5)
_cell_length_b                   8.9258(7)
_cell_length_c                   10.2314(7)
_cell_measurement_temperature    293(2)
_cell_volume                     613.09(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3067
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    5.096
_exptl_crystal_density_diffrn    2.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             382
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0234(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0390P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                2399
_reflns_number_total             2843
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0340042si20030204_083047.cif
_cod_data_source_block           1.TIE
_cod_database_code               4505682
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
I1 I 0.08091(3) 0.20636(2) 0.20493(2) 0.03810(9) Uani 1 1 d .
I2 I -0.31731(4) 0.12290(3) -0.10601(3) 0.05860(11) Uani 1 1 d .
N1 N 0.2112(4) 0.4142(3) 0.4560(3) 0.0357(6) Uani 1 1 d .
C1 C -0.0412(5) 0.0601(4) 0.0186(3) 0.0384(7) Uani 1 1 d .
C2 C 0.2654(5) 0.5515(4) 0.4422(3) 0.0364(7) Uani 1 1 d .
H2AA H 0.2589 0.5736 0.3540 0.044 Uiso 1 1 calc R
C3 C 0.3338(5) 0.6692(3) 0.5541(3) 0.0343(7) Uani 1 1 d .
C4 C 0.3412(5) 0.6377(4) 0.6837(3) 0.0368(7) Uani 1 1 d .
H4AA H 0.3852 0.7123 0.7589 0.044 Uiso 1 1 calc R
C5 C 0.2817(5) 0.4912(4) 0.7026(3) 0.0344(7) Uani 1 1 d .
C6 C 0.2791(6) 0.4524(4) 0.8327(4) 0.0493(9) Uani 1 1 d .
H6AA H 0.3179 0.5248 0.9099 0.059 Uiso 1 1 calc R
C7 C 0.2202(7) 0.3097(5) 0.8454(4) 0.0583(11) Uani 1 1 d .
H7AA H 0.2182 0.2851 0.9311 0.070 Uiso 1 1 calc R
C8 C 0.1627(7) 0.2000(5) 0.7305(5) 0.0568(10) Uani 1 1 d .
H8AA H 0.1252 0.1024 0.7411 0.068 Uiso 1 1 calc R
C9 C 0.1607(6) 0.2338(4) 0.6023(4) 0.0456(8) Uani 1 1 d .
H9AA H 0.1207 0.1596 0.5265 0.055 Uiso 1 1 calc R
C10 C 0.2194(4) 0.3814(3) 0.5852(3) 0.0324(6) Uani 1 1 d .
C11 C 0.3998(5) 0.8137(4) 0.5298(4) 0.0381(7) Uani 1 1 d .
C12 C 0.4626(5) 0.9319(4) 0.5105(3) 0.0379(7) Uani 1 1 d .
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
C1 I1 N1 174.75(11) . .
C2 N1 C10 118.3(3) . .
C2 N1 I1 115.9(2) . .
C10 N1 I1 125.80(19) . .
C1 C1 I2 121.9(3) 2 .
C1 C1 I1 125.2(4) 2 .
I2 C1 I1 112.94(16) . .
N1 C2 C3 123.9(3) . .
C4 C3 C2 118.2(3) . .
C4 C3 C11 122.0(3) . .
C2 C3 C11 119.7(3) . .
C3 C4 C5 119.6(3) . .
C4 C5 C6 122.5(3) . .
C4 C5 C10 117.9(3) . .
C6 C5 C10 119.6(3) . .
C7 C6 C5 120.2(4) . .
C6 C7 C8 120.4(4) . .
C9 C8 C7 121.1(4) . .
C8 C9 C10 119.9(4) . .
N1 C10 C5 122.1(3) . .
N1 C10 C9 119.2(3) . .
C5 C10 C9 118.7(3) . .
C12 C11 C3 177.2(4) . .
C11 C12 C12 179.3(5) . 2_676
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.115(3) .
I1 N1 2.884(3) .
I2 C1 2.104(4) .
N1 C2 1.309(4) .
N1 C10 1.366(4) .
C1 C1 1.319(7) 2
C2 C3 1.423(4) .
C3 C4 1.367(5) .
C3 C11 1.431(4) .
C4 C5 1.413(4) .
C5 C6 1.413(5) .
C5 C10 1.414(4) .
C6 C7 1.360(5) .
C7 C8 1.395(6) .
C8 C9 1.371(6) .
C9 C10 1.414(4) .
C11 C12 1.192(5) .
C12 C12 1.375(6) 2_676
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
_geom_torsion_site_symmetry_4
C1 I1 N1 C2 -91.1(12) .
C1 I1 N1 C10 88.5(12) .
N1 I1 C1 C1 -158.1(9) 2
N1 I1 C1 I2 21.1(13) .
C10 N1 C2 C3 0.4(5) .
I1 N1 C2 C3 -180.0(3) .
N1 C2 C3 C4 -0.8(5) .
N1 C2 C3 C11 176.7(3) .
C2 C3 C4 C5 0.0(5) .
C11 C3 C4 C5 -177.4(3) .
C3 C4 C5 C6 -177.8(3) .
C3 C4 C5 C10 1.1(5) .
C4 C5 C6 C7 179.9(4) .
C10 C5 C6 C7 1.1(5) .
C5 C6 C7 C8 0.4(6) .
C6 C7 C8 C9 -1.2(7) .
C7 C8 C9 C10 0.6(6) .
C2 N1 C10 C5 0.8(5) .
I1 N1 C10 C5 -178.7(2) .
C2 N1 C10 C9 179.8(3) .
I1 N1 C10 C9 0.2(4) .
C4 C5 C10 N1 -1.6(5) .
C6 C5 C10 N1 177.3(3) .
C4 C5 C10 C9 179.5(3) .
C6 C5 C10 C9 -1.6(5) .
C8 C9 C10 N1 -178.2(4) .
C8 C9 C10 C5 0.8(5) .
C4 C3 C11 C12 89(8) .
C2 C3 C11 C12 -88(8) .
C3 C11 C12 C12 -33(48) 2_676
