#------------------------------------------------------------------------------
#$Date: 2019-12-03 07:27:02 +0200 (Tue, 03 Dec 2019) $
#$Revision: 244878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/96/7239614.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_7239614
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                102.8436(7)
_cell_angle_beta                 100.6667(7)
_cell_angle_gamma                107.8250(7)
_cell_formula_units_Z            2
_cell_length_a                   8.5359(2)
_cell_length_b                   9.6656(2)
_cell_length_c                   11.2585(7)
_cell_measurement_reflns_used    18896
_cell_measurement_temperature    296
_cell_measurement_theta_max      45.77
_cell_measurement_theta_min      1.87
_cell_volume                     829.48(6)
_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      296
_diffrn_measured_fraction_theta_full 0.724
_diffrn_measured_fraction_theta_max 0.569
_diffrn_measurement_device_type  'IPDSC (Rigaku)'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68750
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.724
_diffrn_reflns_Laue_measured_fraction_max 0.569
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15309
_diffrn_reflns_point_group_measured_fraction_full 0.724
_diffrn_reflns_point_group_measured_fraction_max 0.569
_diffrn_reflns_theta_full        24.362
_diffrn_reflns_theta_max         34.996
_diffrn_reflns_theta_min         2.520
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.443
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             516.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.82
_refine_diff_density_min         -1.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0456P)²+0.2959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4090
_reflns_number_total             4586
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c9ra06489c2.cif
_cod_data_source_block           anrt_D22bpy-Dia
_cod_database_code               7239614
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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I 1.28458(2) 0.29365(2) 0.92203(2) 0.05019(9) Uani 1 1 d . .
I2 I 1.26191(2) 0.78355(2) 0.89706(2) 0.04990(9) Uani 1 1 d . .
O1 O 0.9502(2) -0.0007(3) 0.75853(13) 0.0522(6) Uani 1 1 d . .
O2 O 1.2636(2) 0.2284(3) 1.18483(13) 0.0512(6) Uani 1 1 d . .
H9 H 1.259616 0.210528 1.252314 0.061 Uiso 1 1 calc R U
O3 O 1.2552(2) 0.7357(3) 1.17046(15) 0.0589(7) Uani 1 1 d . .
O4 O 0.9352(2) 0.4785(3) 0.74838(13) 0.0497(6) Uani 1 1 d . .
H10 H 0.853248 0.399188 0.711213 0.060 Uiso 1 1 calc R U
N1 N 0.3153(2) 0.2835(3) 0.43434(15) 0.0437(6) Uani 1 1 d . .
N2 N 0.7144(2) 0.2423(3) 0.55437(14) 0.0409(6) Uani 1 1 d . .
C1 C 0.4532(2) 0.2948(3) 0.52158(15) 0.0359(7) Uani 1 1 d . .
C2 C 0.2139(3) 0.3587(4) 0.4667(2) 0.0519(9) Uani 1 1 d . .
H1 H 0.118120 0.348051 0.405246 0.062 Uiso 1 1 calc R U
C3 C 0.2460(3) 0.4514(4) 0.5878(2) 0.0503(10) Uani 1 1 d . .
H2 H 0.172908 0.501485 0.608437 0.060 Uiso 1 1 calc R U
C4 C 0.3902(3) 0.4675(4) 0.6775(2) 0.0507(9) Uani 1 1 d . .
H3 H 0.417726 0.531636 0.759301 0.061 Uiso 1 1 calc R U
C5 C 0.4929(3) 0.3883(4) 0.64504(17) 0.0465(8) Uani 1 1 d . .
H4 H 0.588719 0.397057 0.705473 0.056 Uiso 1 1 calc R U
C6 C 0.5560(2) 0.2058(3) 0.47915(15) 0.0369(7) Uani 1 1 d . .
C7 C 0.8127(3) 0.1631(4) 0.5218(2) 0.0518(9) Uani 1 1 d . .
H5 H 0.919598 0.187499 0.576690 0.062 Uiso 1 1 calc R U
C8 C 0.7606(3) 0.0469(4) 0.4100(2) 0.0511(10) Uani 1 1 d . .
H6 H 0.832608 -0.003507 0.387581 0.061 Uiso 1 1 calc R U
C9 C 0.5981(3) 0.0075(4) 0.3322(2) 0.0477(8) Uani 1 1 d . .
H7 H 0.558803 -0.071026 0.256538 0.057 Uiso 1 1 calc R U
C10 C 0.4948(3) 0.0852(3) 0.36728(17) 0.0418(7) Uani 1 1 d . .
H8 H 0.384367 0.057369 0.316437 0.050 Uiso 1 1 calc R U
C11 C 0.9786(2) 0.0041(3) 0.87103(16) 0.0370(7) Uani 1 1 d . .
C12 C 1.1168(2) 0.1229(3) 0.97005(16) 0.0360(7) Uani 1 1 d . .
C13 C 1.1397(3) 0.1214(3) 1.09346(16) 0.0371(7) Uani 1 1 d . .
C14 C 1.1391(2) 0.6287(3) 1.08809(18) 0.0398(7) Uani 1 1 d . .
C15 C 1.1030(2) 0.6172(3) 0.95523(17) 0.0368(7) Uani 1 1 d . .
C16 C 0.9715(2) 0.4951(3) 0.86920(18) 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 0.0019 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_3
C13 O2 H9 109.5 .
C16 O4 H10 109.5 .
C2 N1 C1 120.14(18) .
C7 N2 C6 120.24(18) .
N1 C1 C5 119.7(2) .
N1 C1 C6 116.84(16) .
C5 C1 C6 123.43(18) .
N1 C2 C3 122.5(2) .
N1 C2 H1 118.7 .
C3 C2 H1 118.7 .
C2 C3 C4 117.9(2) .
C2 C3 H2 121.1 .
C4 C3 H2 121.1 .
C5 C4 C3 119.7(2) .
C5 C4 H3 120.2 .
C3 C4 H3 120.2 .
C4 C5 C1 120.0(2) .
C4 C5 H4 120.0 .
C1 C5 H4 120.0 .
N2 C6 C10 119.6(2) .
N2 C6 C1 117.58(17) .
C10 C6 C1 122.80(18) .
N2 C7 C8 122.4(2) .
N2 C7 H5 118.8 .
C8 C7 H5 118.8 .
C7 C8 C9 118.1(2) .
C7 C8 H6 121.0 .
C9 C8 H6 121.0 .
C10 C9 C8 119.7(2) .
C10 C9 H7 120.2 .
C8 C9 H7 120.2 .
C9 C10 C6 119.96(19) .
C9 C10 H8 120.0 .
C6 C10 H8 120.0 .
O1 C11 C12 123.9(3) .
O1 C11 C13 117.8(2) 2_757
C12 C11 C13 118.30(17) 2_757
C13 C12 C11 120.6(2) .
C13 C12 I1 120.61(17) .
C11 C12 I1 118.74(15) .
O2 C13 C12 121.7(3) .
O2 C13 C11 117.26(18) 2_757
C12 C13 C11 121.07(19) 2_757
O3 C14 C15 123.6(3) .
O3 C14 C16 117.3(2) 2_767
C15 C14 C16 119.10(19) 2_767
C16 C15 C14 120.3(2) .
C16 C15 I2 120.99(17) .
C14 C15 I2 118.68(16) .
O4 C16 C15 122.6(3) .
O4 C16 C14 116.75(19) 2_767
C15 C16 C14 120.64(19) 2_767
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C12 2.074(3) .
I2 C15 2.077(3) .
O1 C11 1.232(2) .
O2 C13 1.304(3) .
O2 H9 0.8200 .
O3 C14 1.232(3) .
O4 C16 1.299(2) .
O4 H10 0.8200 .
N1 C2 1.340(3) .
N1 C1 1.345(3) .
N2 C7 1.344(3) .
N2 C6 1.349(2) .
C1 C5 1.394(2) .
C1 C6 1.474(4) .
C2 C3 1.380(3) .
C2 H1 0.9300 .
C3 C4 1.383(4) .
C3 H2 0.9300 .
C4 C5 1.376(4) .
C4 H3 0.9300 .
C5 H4 0.9300 .
C6 C10 1.396(3) .
C7 C8 1.379(3) .
C7 H5 0.9300 .
C8 C9 1.384(3) .
C8 H6 0.9300 .
C9 C10 1.379(4) .
C9 H7 0.9300 .
C10 H8 0.9300 .
C11 C12 1.438(3) .
C11 C13 1.505(4) 2_757
C12 C13 1.371(3) .
C14 C15 1.442(3) .
C14 C16 1.512(4) 2_767
C15 C16 1.368(3) .
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 -1.7(4) . .
C2 N1 C1 C6 178.6(3) . .
C1 N1 C2 C3 1.0(5) . .
N1 C2 C3 C4 0.9(5) . .
C2 C3 C4 C5 -2.0(5) . .
C3 C4 C5 C1 1.4(5) . .
N1 C1 C5 C4 0.6(4) . .
C6 C1 C5 C4 -179.8(3) . .
C7 N2 C6 C10 0.0(4) . .
C7 N2 C6 C1 178.7(3) . .
N1 C1 C6 N2 164.4(2) . .
C5 C1 C6 N2 -15.2(4) . .
N1 C1 C6 C10 -17.0(4) . .
C5 C1 C6 C10 163.4(2) . .
C6 N2 C7 C8 2.5(5) . .
N2 C7 C8 C9 -2.8(5) . .
C7 C8 C9 C10 0.6(5) . .
C8 C9 C10 C6 1.8(5) . .
N2 C6 C10 C9 -2.1(4) . .
C1 C6 C10 C9 179.3(3) . .
O1 C11 C12 C13 179.5(2) . .
C13 C11 C12 C13 0.0(4) 2_757 .
O1 C11 C12 I1 -2.1(3) . .
C13 C11 C12 I1 178.48(16) 2_757 .
C11 C12 C13 O2 -179.6(2) . .
I1 C12 C13 O2 2.0(3) . .
C11 C12 C13 C11 0.0(4) . 2_757
I1 C12 C13 C11 -178.45(16) . 2_757
O3 C14 C15 C16 -179.8(3) . .
C16 C14 C15 C16 -0.6(4) 2_767 .
O3 C14 C15 I2 3.2(3) . .
C16 C14 C15 I2 -177.56(16) 2_767 .
C14 C15 C16 O4 -179.1(2) . .
I2 C15 C16 O4 -2.2(3) . .
C14 C15 C16 C14 0.6(4) . 2_767
I2 C15 C16 C14 177.50(16) . 2_767
