#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/09/7200925.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_7200925
loop_
_publ_author_name
'Horiuchi, Sachio'
'Kumai, Reiji'
'Tokura, Yoshinori'
_publ_section_title
;
 Proton-displacive ferroelectricity in neutral cocrystals of anilic
 acids with phenazine
;
_journal_issue                   25
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              4421
_journal_paper_doi               10.1039/b900987f
_journal_volume                  19
_journal_year                    2009
_chemical_formula_moiety         'C18 H10 I2 N2 O4 '
_chemical_formula_sum            'C18 H10 I2 N2 O4'
_chemical_formula_weight         572.10
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.939(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   12.300(4)
_cell_length_b                   4.9829(13)
_cell_length_c                   15.271(5)
_cell_measurement_reflns_used    3351
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     895.3(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8545
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    3.540
_exptl_absorpt_correction_T_max  0.838
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Higashi, T. (1999). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             540.00
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.61
_refine_ls_extinction_coef       10(3)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.815
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1503
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.0025
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(Fo)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0203
_reflns_number_gt                1503
_reflns_number_total             2037
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b900987f.txt
_cod_data_source_block           '_Phz-H2ia(beta-form)'
_cod_original_cell_volume        895.3(4)
_cod_original_formula_sum        'C18 H10 I2 N2 O4 '
_cod_database_code               7200925
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+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
_atom_site_disorder_assembly
_atom_site_disorder_group
I(1) I 0.56837(2) 0.01891(5) 0.67682(2) 0.03944(9) Uani 1.00 1 d . . .
O(1) O 0.3366(2) 0.3095(5) 0.5734(2) 0.0444(9) Uani 1.00 1 d . . .
O(2) O 0.2868(2) 0.6633(5) 0.4350(2) 0.0579(10) Uani 1.00 1 d . . .
N(1) N 0.1172(2) 0.4497(6) 0.5209(2) 0.0321(9) Uani 1.00 1 d . . .
C(1) C 0.5254(3) 0.2999(6) 0.5723(2) 0.0258(10) Uani 1.00 1 d . . .
C(2) C 0.4183(3) 0.3924(6) 0.5402(2) 0.0278(10) Uani 1.00 1 d . . .
C(3) C 0.3862(3) 0.5972(6) 0.4633(2) 0.0313(11) Uani 1.00 1 d . . .
C(4) C 0.0421(3) 0.3098(6) 0.4553(2) 0.0300(11) Uani 1.00 1 d . . .
C(5) C 0.0802(4) 0.1055(7) 0.4060(3) 0.0433(14) Uani 1.00 1 d . . .
C(6) C 0.0051(4) -0.0343(9) 0.3412(3) 0.0533(15) Uani 1.00 1 d . . .
C(7) C -0.1129(4) 0.0134(10) 0.3202(2) 0.0572(14) Uani 1.00 1 d . . .
C(8) C -0.1533(4) 0.2045(8) 0.3657(3) 0.0465(14) Uani 1.00 1 d . . .
C(9) C -0.0771(3) 0.3611(7) 0.4344(2) 0.0315(11) Uani 1.00 1 d . . .
H(1) H 0.273(5) 0.384(10) 0.549(4) 0.11(2) Uiso 1.00 1 d . . .
H(2) H 0.1593 0.0697 0.4201 0.056 Uiso 1.00 1 c R . .
H(3) H 0.0317 -0.1683 0.3082 0.067 Uiso 1.00 1 c R . .
H(4) H -0.1642 -0.0905 0.2742 0.067 Uiso 1.00 1 c R . .
H(5) H -0.2328 0.2352 0.3519 0.054 Uiso 1.00 1 c R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
I I -0.474 1.812
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C(4) N(1) C(9) 118.1(3) yes . . 3_566
I(1) C(1) C(2) 120.9(3) yes . . .
I(1) C(1) C(3) 118.6(2) yes . . 3_666
C(2) C(1) C(3) 120.4(3) yes . . 3_666
O(1) C(2) C(1) 121.9(3) yes . . .
O(1) C(2) C(3) 116.9(3) yes . . .
C(1) C(2) C(3) 121.2(3) yes . . .
O(2) C(3) C(1) 123.9(3) yes . . 3_666
O(2) C(3) C(2) 117.7(4) yes . . .
C(1) C(3) C(2) 118.4(3) yes 3_666 . .
N(1) C(4) C(5) 120.3(3) yes . . .
N(1) C(4) C(9) 120.7(3) yes . . .
C(5) C(4) C(9) 118.9(3) yes . . .
C(4) C(5) C(6) 120.1(4) yes . . .
C(5) C(6) C(7) 121.5(4) yes . . .
C(6) C(7) C(8) 120.6(4) yes . . .
C(7) C(8) C(9) 120.2(4) yes . . .
N(1) C(9) C(4) 121.2(3) yes 3_566 . .
N(1) C(9) C(8) 120.1(3) yes 3_566 . .
C(4) C(9) C(8) 118.7(3) yes . . .
C(2) O(1) H(1) 114(4) no . . .
C(4) C(5) H(2) 119.2 no . . .
C(6) C(5) H(2) 120.7 no . . .
C(5) C(6) H(3) 119.3 no . . .
C(7) C(6) H(3) 119.2 no . . .
C(6) C(7) H(4) 119.5 no . . .
C(8) C(7) H(4) 119.9 no . . .
C(7) C(8) H(5) 120.4 no . . .
C(9) C(8) H(5) 119.4 no . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
I(1) C(1) 2.073(3) yes . .
O(1) C(2) 1.317(5) yes . .
O(2) C(3) 1.217(4) yes . .
N(1) C(4) 1.343(4) yes . .
N(1) C(9) 1.339(5) yes . 3_566
C(1) C(2) 1.346(5) yes . .
C(1) C(3) 1.443(6) yes . 3_666
C(2) C(3) 1.519(5) yes . .
C(4) C(5) 1.424(6) yes . .
C(4) C(9) 1.430(5) yes . .
C(5) C(6) 1.336(6) yes . .
C(6) C(7) 1.413(8) yes . .
C(7) C(8) 1.355(7) yes . .
C(8) C(9) 1.420(5) yes . .
O(1) H(1) 0.85(5) no . .
C(5) H(2) 0.950 no . .
C(6) H(3) 0.950 no . .
C(7) H(4) 0.950 no . .
C(8) H(5) 0.950 no . .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O(1) N(1) 2.675(4) ? . .
O(1) C(4) 3.545(5) ? . .
O(1) C(5) 3.580(5) ? . .
O(1) C(9) 3.560(5) ? . 3_566
O(2) N(1) 2.967(5) ? . .
O(2) C(4) 3.579(5) ? . .
O(2) C(5) 3.295(5) ? . 1_565
N(1) O(1) 2.675(4) ? . .
N(1) O(2) 2.967(5) ? . .
N(1) C(6) 3.582(6) ? . 3_556
N(1) C(7) 3.359(5) ? . 3_556
C(4) O(1) 3.545(5) ? . .
C(4) O(2) 3.579(5) ? . .
C(4) C(5) 3.589(6) ? . 3_556
C(4) C(6) 3.597(6) ? . 3_556
C(5) O(1) 3.580(5) ? . .
C(5) O(2) 3.295(5) ? . 1_545
C(5) C(4) 3.589(6) ? . 3_556
C(5) C(9) 3.376(5) ? . 3_556
C(6) N(1) 3.582(6) ? . 3_556
C(6) C(4) 3.597(6) ? . 3_556
C(7) N(1) 3.359(5) ? . 3_556
C(9) O(1) 3.560(5) ? . 3_566
C(9) C(5) 3.376(5) ? . 3_556
I(1) H(5) 3.289 ? . 4_655
O(1) H(2) 2.948 ? . .
O(1) H(5) 3.339 ? . 3_556
O(1) H(5) 2.988 ? . 3_566
O(2) H(2) 3.325 ? . .
O(2) H(2) 2.531 ? . 1_565
O(2) H(3) 3.280 ? . 1_565
O(2) H(4) 3.357 ? . 2_555
O(2) H(5) 3.543 ? . 3_566
N(1) H(1) 1.86(6) ? . .
N(1) H(2) 3.556 ? . 1_565
N(1) H(4) 3.504 ? . 3_556
C(2) H(2) 3.563 ? . .
C(3) H(2) 3.563 ? . 1_565
C(4) H(1) 2.80(5) ? . .
C(4) H(3) 3.415 ? . 1_565
C(5) H(1) 3.04(5) ? . .
C(5) H(3) 3.353 ? . 2_555
C(5) H(4) 3.549 ? . 2_555
C(6) H(3) 2.851 ? . 2_555
C(7) H(3) 2.916 ? . 2_555
C(8) H(1) 3.03(6) ? . 3_566
C(8) H(2) 3.565 ? . 3_556
C(8) H(3) 3.465 ? . 2_555
C(9) H(1) 2.80(6) ? . 3_566
C(9) H(2) 3.446 ? . 3_556
C(9) H(3) 3.537 ? . 1_565
H(1) N(1) 1.86(6) ? . .
H(1) C(4) 2.80(5) ? . .
H(1) C(5) 3.04(5) ? . .
H(1) C(8) 3.03(6) ? . 3_566
H(1) C(9) 2.80(6) ? . 3_566
H(1) H(2) 2.580 ? . .
H(1) H(5) 3.534 ? . 3_556
H(1) H(5) 2.565 ? . 3_566
H(2) O(1) 2.948 ? . .
H(2) O(2) 2.531 ? . 1_545
H(2) O(2) 3.325 ? . .
H(2) N(1) 3.556 ? . 1_545
H(2) C(2) 3.563 ? . .
H(2) C(3) 3.563 ? . 1_545
H(2) C(8) 3.565 ? . 3_556
H(2) C(9) 3.446 ? . 3_556
H(2) H(1) 2.580 ? . .
H(2) H(4) 3.432 ? . 2_555
H(3) O(2) 3.280 ? . 1_545
H(3) C(4) 3.415 ? . 1_545
H(3) C(5) 3.353 ? . 2_545
H(3) C(6) 2.851 ? . 2_545
H(3) C(7) 2.916 ? . 2_545
H(3) C(8) 3.465 ? . 2_545
H(3) C(9) 3.537 ? . 1_545
H(3) H(3) 3.027 ? . 2_545
H(3) H(3) 3.027 ? . 2_555
H(3) H(4) 3.140 ? . 2_545
H(4) O(2) 3.357 ? . 2_545
H(4) N(1) 3.504 ? . 3_556
H(4) C(5) 3.549 ? . 2_545
H(4) H(2) 3.432 ? . 2_545
H(4) H(3) 3.140 ? . 2_555
H(5) I(1) 3.289 ? . 4_454
H(5) O(1) 3.339 ? . 3_556
H(5) O(1) 2.988 ? . 3_566
H(5) O(2) 3.543 ? . 3_566
H(5) H(1) 3.534 ? . 3_556
H(5) H(1) 2.565 ? . 3_566
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O(1) H(1) O(2) . . . 2.682(4) 0.85(5) 2.27(6) 110(5) no
O(1) H(1) N(1) . . . 2.675(4) 0.85(5) 1.86(6) 159(6) no
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C(4) N(1) C(9) C(4) 0.4(5) ? . . 3_566 3_566
C(4) N(1) C(9) C(8) -178.8(3) ? . . 3_566 3_566
C(9) N(1) C(4) C(5) -179.7(3) ? 3_566 . . .
C(9) N(1) C(4) C(9) -0.4(5) ? 3_566 . . .
I(1) C(1) C(2) O(1) -0.0(3) ? . . . .
I(1) C(1) C(2) C(3) -179.7(2) ? . . . .
I(1) C(1) C(3) O(2) -0.8(4) ? . . 3_666 3_666
I(1) C(1) C(3) C(2) 179.7(2) ? . . 3_666 3_666
C(2) C(1) C(3) O(2) 176.8(3) ? . . 3_666 3_666
C(2) C(1) C(3) C(2) -2.6(5) ? . . 3_666 3_666
C(3) C(1) C(2) O(1) -177.6(3) ? 3_666 . . .
C(3) C(1) C(2) C(3) 2.7(5) ? 3_666 . . .
O(1) C(2) C(3) O(2) -2.8(5) ? . . . .
O(1) C(2) C(3) C(1) 177.7(3) ? . . . 3_666
C(1) C(2) C(3) O(2) 176.9(3) ? . . . .
C(1) C(2) C(3) C(1) -2.6(5) ? . . . 3_666
N(1) C(4) C(5) C(6) 179.6(4) ? . . . .
N(1) C(4) C(9) N(1) 0.4(6) ? . . . 3_566
N(1) C(4) C(9) C(8) -178.8(3) ? . . . .
C(5) C(4) C(9) N(1) 179.7(3) ? . . . 3_566
C(5) C(4) C(9) C(8) 0.5(5) ? . . . .
C(9) C(4) C(5) C(6) 0.3(6) ? . . . .
C(4) C(5) C(6) C(7) -0.7(7) ? . . . .
C(5) C(6) C(7) C(8) 0.2(6) ? . . . .
C(6) C(7) C(8) C(9) 0.6(7) ? . . . .
C(7) C(8) C(9) N(1) 179.8(4) ? . . . 3_566
C(7) C(8) C(9) C(4) -1.0(6) ? . . . .
