#------------------------------------------------------------------------------
#$Date: 2019-11-25 06:32:15 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240238 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/95/4129535.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_4129535
loop_
_publ_author_name
'Rupasinghe, Thilini P.'
'Hutchins, Kristin M.'
'Bandaranayake, Bimali S.'
'Ghorai, Suman'
'Karunatilake, Chandana'
'Bučar, Dejan-Krešimir'
'Swenson, Dale C.'
'Arnold, Mark A.'
'MacGillivray, Leonard R.'
'Tivanski, Alexei V.'
_publ_section_title
;
 Mechanical Properties of a Series of Macro- and Nanodimensional Organic
 Cocrystals Correlate with Atomic Polarizability.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12768
_journal_page_last               12771
_journal_paper_doi               10.1021/jacs.5b07873
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C12 H10 N2, C6 H4 I2 O2'
_chemical_formula_sum            'C18 H14 I2 N2 O2'
_chemical_formula_weight         544.11
_chemical_name_common            'BPE.4,6-diIodo res'
_chemical_name_systematic
; 
'4,4'-(1,2-ethenediyl)bispyridine 4,6-diiodo-1,3-benzenediol' 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                75.671(5)
_cell_angle_beta                 70.310(5)
_cell_angle_gamma                64.891(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2179(10)
_cell_length_b                   10.6179(12)
_cell_length_c                   11.0370(12)
_cell_measurement_reflns_used    4181
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     914.02(18)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD 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  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5767
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    3.453
_exptl_absorpt_correction_T_max  0.8196
_exptl_absorpt_correction_T_min  0.4141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.977
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0221
_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)+(0.0222P)²+1.2375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0570
_reflns_number_gt                2915
_reflns_number_total             3194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b07873_si_002.cif
_cod_data_source_block           mcg1092
_cod_original_cell_volume        914.02(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4129535
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
I2 I -0.16588(3) 0.38448(2) 0.22150(2) 0.04491(8) Uani 1 1 d .
I1 I 0.33048(3) 0.41510(3) 0.44075(2) 0.04757(9) Uani 1 1 d .
O1 O 0.1650(3) 0.2738(3) 0.0005(2) 0.0478(6) Uani 1 1 d .
H1O H 0.2481 0.2481 -0.0597 0.072 Uiso 1 1 calc R
O2 O 0.5593(3) 0.3035(4) 0.1751(3) 0.0605(8) Uani 1 1 d .
H2O H 0.6223 0.2751 0.1063 0.091 Uiso 1 1 calc R
C17 C 0.1166(4) 0.3853(3) 0.3014(3) 0.0337(7) Uani 1 1 d .
H17 H 0.0331 0.4165 0.3755 0.040 Uiso 1 1 calc R
C15 C 0.4039(4) 0.3210(4) 0.1809(3) 0.0376(7) Uani 1 1 d .
C14 C 0.3648(4) 0.2911(4) 0.0835(3) 0.0407(8) Uani 1 1 d .
H14 H 0.4486 0.2597 0.0095 0.049 Uiso 1 1 calc R
C13 C 0.2042(4) 0.3064(3) 0.0930(3) 0.0358(7) Uani 1 1 d .
C18 C 0.0792(4) 0.3556(3) 0.2037(3) 0.0336(7) Uani 1 1 d .
C16 C 0.2766(4) 0.3695(3) 0.2906(3) 0.0334(7) Uani 1 1 d .
N1 N 0.4340(4) 0.1742(3) 0.7932(3) 0.0514(8) Uani 1 1 d .
C1 C 0.4532(5) 0.0607(4) 0.7485(4) 0.0581(10) Uani 1 1 d .
H1 H 0.3808 0.0146 0.7934 0.070 Uiso 1 1 calc R
C2 C 0.5745(5) 0.0079(4) 0.6394(3) 0.0537(10) Uani 1 1 d .
H2 H 0.5828 -0.0719 0.6125 0.064 Uiso 1 1 calc R
C3 C 0.6843(4) 0.0752(4) 0.5702(3) 0.0434(8) Uani 1 1 d .
C5 C 0.5390(5) 0.2377(4) 0.7264(4) 0.0515(9) Uani 1 1 d .
H5 H 0.5277 0.3173 0.7555 0.062 Uiso 1 1 calc R
C7 C 0.8493(4) -0.0783(4) 0.3954(3) 0.0478(9) Uani 1 1 d .
H7 H 0.7912 -0.1369 0.4387 0.057 Uiso 1 1 calc R
C4 C 0.6643(5) 0.1927(4) 0.6160(3) 0.0483(8) Uani 1 1 d .
H4 H 0.7344 0.2414 0.5731 0.058 Uiso 1 1 calc R
C6 C 0.8128(5) 0.0311(4) 0.4501(3) 0.0485(9) Uani 1 1 d .
H6 H 0.8746 0.0871 0.4086 0.058 Uiso 1 1 calc R
C8 C 0.9736(4) -0.1181(4) 0.2718(3) 0.0411(8) Uani 1 1 d .
C12 C 1.0574(5) -0.0342(4) 0.1910(4) 0.0527(9) Uani 1 1 d .
H12 H 1.0349 0.0527 0.2126 0.063 Uiso 1 1 calc R
C9 C 1.0110(5) -0.2435(4) 0.2315(4) 0.0518(9) Uani 1 1 d .
H9 H 0.9559 -0.3026 0.2813 0.062 Uiso 1 1 calc R
N2 N 1.2124(3) -0.2034(3) 0.0411(3) 0.0465(7) Uani 1 1 d .
C10 C 1.1296(5) -0.2817(4) 0.1179(4) 0.0508(9) Uani 1 1 d .
H10 H 1.1530 -0.3675 0.0936 0.061 Uiso 1 1 calc R
C11 C 1.1746(5) -0.0803(4) 0.0782(4) 0.0564(10) Uani 1 1 d .
H11 H 1.2300 -0.0226 0.0253 0.068 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'
O O 0.0106 0.0060 '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
C13 O1 H1O 109.5
C15 O2 H2O 109.5
C18 C17 C16 120.7(3)
C18 C17 H17 119.7
C16 C17 H17 119.7
O2 C15 C14 122.9(3)
O2 C15 C16 118.7(3)
C14 C15 C16 118.4(3)
C15 C14 C13 121.9(3)
C15 C14 H14 119.1
C13 C14 H14 119.1
O1 C13 C14 122.6(3)
O1 C13 C18 118.9(3)
C14 C13 C18 118.5(3)
C17 C18 C13 120.2(3)
C17 C18 I2 119.8(2)
C13 C18 I2 120.1(2)
C17 C16 C15 120.4(3)
C17 C16 I1 120.0(2)
C15 C16 I1 119.6(2)
C5 N1 C1 116.5(3)
N1 C1 C2 123.7(4)
N1 C1 H1 118.1
C2 C1 H1 118.1
C1 C2 C3 119.3(4)
C1 C2 H2 120.3
C3 C2 H2 120.3
C4 C3 C2 117.0(3)
C4 C3 C6 119.3(3)
C2 C3 C6 123.6(3)
N1 C5 C4 123.9(4)
N1 C5 H5 118.0
C4 C5 H5 118.0
C6 C7 C8 126.4(3)
C6 C7 H7 116.8
C8 C7 H7 116.8
C3 C4 C5 119.5(4)
C3 C4 H4 120.3
C5 C4 H4 120.3
C7 C6 C3 126.9(4)
C7 C6 H6 116.6
C3 C6 H6 116.6
C9 C8 C12 116.6(3)
C9 C8 C7 120.3(3)
C12 C8 C7 123.1(3)
C11 C12 C8 119.6(3)
C11 C12 H12 120.2
C8 C12 H12 120.2
C10 C9 C8 120.1(3)
C10 C9 H9 120.0
C8 C9 H9 120.0
C10 N2 C11 116.6(3)
N2 C10 C9 123.7(3)
N2 C10 H10 118.1
C9 C10 H10 118.1
N2 C11 C12 123.3(4)
N2 C11 H11 118.3
C12 C11 H11 118.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I2 C18 2.093(3)
I1 C16 2.094(3)
O1 C13 1.350(4)
O1 H1O 0.8200
O2 C15 1.345(4)
O2 H2O 0.8200
C17 C18 1.376(4)
C17 C16 1.378(4)
C17 H17 0.9300
C15 C14 1.383(5)
C15 C16 1.395(4)
C14 C13 1.389(5)
C14 H14 0.9300
C13 C18 1.396(4)
N1 C5 1.327(5)
N1 C1 1.334(5)
C1 C2 1.382(5)
C1 H1 0.9300
C2 C3 1.393(5)
C2 H2 0.9300
C3 C4 1.379(5)
C3 C6 1.469(4)
C5 C4 1.385(5)
C5 H5 0.9300
C7 C6 1.306(5)
C7 C8 1.474(4)
C7 H7 0.9300
C4 H4 0.9300
C6 H6 0.9300
C8 C9 1.375(5)
C8 C12 1.383(5)
C12 C11 1.379(5)
C12 H12 0.9300
C9 C10 1.372(5)
C9 H9 0.9300
N2 C10 1.322(5)
N2 C11 1.334(5)
C10 H10 0.9300
C11 H11 0.9300
