#------------------------------------------------------------------------------
#$Date: 2019-12-03 07:27:02 +0200 (Tue, 03 Dec 2019) $
#$Revision: 244878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/96/7239615.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_7239615
loop_
_publ_author_name
'Horiuchi, Sachio'
'Ishibashi, Shoji'
'Kobayashi, Kensuke'
'Kumai, Reiji'
_publ_section_title
;
 Coexistence of normal and inverse deuterium isotope effects in a
 phase-transition sequence of organic ferroelectrics
;
_journal_issue                   68
_journal_name_full               'RSC Advances'
_journal_page_first              39662
_journal_paper_doi               10.1039/C9RA06489C
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C16 H10 I2 N2 O4'
_chemical_formula_sum            'C16 H10 I2 N2 O4'
_chemical_formula_weight         548.07
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-10-24 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                102.1304(9)
_cell_angle_beta                 101.7257(10)
_cell_angle_gamma                104.5226(11)
_cell_formula_units_Z            1
_cell_length_a                   4.8002(3)
_cell_length_b                   8.5129(5)
_cell_length_c                   11.2407(7)
_cell_measurement_reflns_used    4465
_cell_measurement_temperature    375
_cell_measurement_theta_max      38.70
_cell_measurement_theta_min      1.86
_cell_volume                     418.54(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      375
_diffrn_measured_fraction_theta_full 0.744
_diffrn_measured_fraction_theta_max 0.668
_diffrn_measurement_device_type  'IPDSC (Rigaku)'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68750
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.744
_diffrn_reflns_Laue_measured_fraction_max 0.668
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3497
_diffrn_reflns_point_group_measured_fraction_full 0.744
_diffrn_reflns_point_group_measured_fraction_max 0.668
_diffrn_reflns_theta_full        24.362
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         1.862
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.412
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             258.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.83
_refine_diff_density_min         -0.77
_refine_ls_extinction_coef       0.266(13)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0611P)²+0.1931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1672
_reflns_number_total             1798
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c9ra06489c2.cif
_cod_data_source_block           375K_D22bpy-Dia
_cod_database_code               7239615
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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_site_symmetry_order
_atom_site_calc_flag
I1 I 0.10796(8) 0.27371(4) 0.41192(3) 0.0739(3) Uani 1 1 d
O1 O 0.4766(11) 0.2575(4) 0.6790(3) 0.0797(12) Uani 1 1 d
O2 O 0.7815(9) 0.0572(4) 0.7460(2) 0.0719(10) Uani 1 1 d
N1 N 0.7075(10) 0.3010(4) 0.9409(3) 0.0705(12) Uani 1 1 d
C1 C 0.8817(9) 0.4488(4) 1.0215(2) 0.0494(10) Uani 1 1 d
C2 C 0.4867(14) 0.2027(6) 0.9742(4) 0.0783(17) Uani 1 1 d
C3 C 0.4338(14) 0.2456(6) 1.0901(4) 0.0694(15) Uani 1 1 d
C4 C 0.6077(14) 0.3970(6) 1.1729(3) 0.0724(15) Uani 1 1 d
C5 C 0.8323(12) 0.4997(5) 1.1385(3) 0.0654(13) Uani 1 1 d
C6 C 0.3342(9) 0.1093(4) 0.4634(3) 0.0519(10) Uani 1 1 d
C7 C 0.4809(10) 0.1392(4) 0.5914(3) 0.0554(11) Uani 1 1 d
C8 C 0.6542(9) 0.0246(4) 0.6291(3) 0.0533(11) Uani 1 1 d
H1 H 0.368(14) 0.104(6) 0.904(5) 0.069(14) Uiso 1 1 d
H2 H 0.254(19) 0.176(9) 1.111(7) 0.093(19) Uiso 1 1 d
H3 H 0.538(18) 0.431(8) 1.248(6) 0.096(19) Uiso 1 1 d
H4 H 0.958(14) 0.600(7) 1.203(5) 0.074(15) Uiso 1 1 d
H5 H 0.638(15) 0.217(7) 0.783(5) 0.071(15) Uiso 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 0.0019 0.0015
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0056 0.0031
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0100 0.0057
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4915 1.7168
;
International Tables for Crystallography
(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
C7 O1 H5 98(2) . .
C1 N1 C2 119.9(3) . .
N1 C1 C5 119.6(3) . .
N1 C1 C1 117.1(3) . 2_767
C5 C1 C1 123.3(3) . 2_767
N1 C2 C3 122.7(4) . .
N1 C2 H1 111(3) . .
C3 C2 H1 126(3) . .
C4 C3 C2 118.1(4) . .
C4 C3 H2 120(4) . .
C2 C3 H2 122(4) . .
C3 C4 C5 119.5(4) . .
C3 C4 H3 115(4) . .
C5 C4 H3 125(4) . .
C1 C5 C4 120.2(3) . .
C1 C5 H4 124(3) . .
C4 C5 H4 116(3) . .
C8 C6 C7 121.3(4) 2_656 .
C8 C6 I1 119.8(3) 2_656 .
C7 C6 I1 118.9(3) . .
O1 C7 C6 124.0(5) . .
O1 C7 C8 116.7(3) . .
C6 C7 C8 119.3(3) . .
O2 C8 C6 123.9(4) . 2_656
O2 C8 C7 116.7(3) . .
C6 C8 C7 119.4(3) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C6 2.079(5) .
O1 C7 1.259(5) .
O1 H5 1.42(7) .
O2 C8 1.270(4) .
N1 C1 1.337(4) .
N1 C2 1.346(6) .
C1 C5 1.382(4) .
C1 C1 1.479(7) 2_767
C2 C3 1.369(6) .
C2 H1 0.98(5) .
C3 C4 1.365(7) .
C3 H2 1.02(8) .
C4 C5 1.385(6) .
C4 H3 0.98(7) .
C5 H4 0.96(5) .
C6 C8 1.393(5) 2_656
C6 C7 1.405(5) .
C7 C8 1.503(7) .
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_1
_geom_torsion_site_symmetry_4
C2 N1 C1 C5 -0.4(7) . .
C2 N1 C1 C1 -179.5(6) . 2_767
C1 N1 C2 C3 -1.3(9) . .
N1 C2 C3 C4 2.0(10) . .
C2 C3 C4 C5 -1.0(9) . .
N1 C1 C5 C4 1.3(8) . .
C1 C1 C5 C4 -179.7(6) 2_767 .
C3 C4 C5 C1 -0.6(9) . .
C8 C6 C7 O1 -179.6(4) 2_656 .
I1 C6 C7 O1 2.4(5) . .
C8 C6 C7 C8 0.1(6) 2_656 .
I1 C6 C7 C8 -177.9(2) . .
O1 C7 C8 O2 -0.1(5) . .
C6 C7 C8 O2 -179.8(3) . .
O1 C7 C8 C6 179.6(4) . 2_656
C6 C7 C8 C6 -0.1(5) . 2_656
