#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/09/7200924.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_7200924
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 Br2 N2 O4 '
_chemical_formula_sum            'C18 H10 Br2 N2 O4'
_chemical_formula_weight         478.10
_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                 107.6042(17)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   12.299(2)
_cell_length_b                   4.8114(8)
_cell_length_c                   15.153(3)
_cell_measurement_reflns_used    2938
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.5
_cell_volume                     854.7(3)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.032
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8159
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    4.784
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Higashi, T. (1999). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             468.00
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.87
_refine_diff_density_min         -0.57
_refine_ls_extinction_coef       19(6)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1325
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.0094
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0007Fo² + 1.0000σ(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0499
_reflns_number_gt                1308
_reflns_number_total             1924
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b900987f.txt
_cod_data_source_block           '__Phz-H2ba(beta-form)'
_cod_original_formula_sum        'C18 H10 Br2 N2 O4 '
_cod_database_code               7200924
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
Br(1) Br 0.56644(4) 0.04733(11) 0.67311(4) 0.05553(18) Uani 1.00 1 d . . .
O(1) O 0.3353(2) 0.2897(7) 0.5696(2) 0.0627(11) Uani 1.00 1 d . . .
O(2) O 0.2838(2) 0.6459(8) 0.4254(2) 0.0695(12) Uani 1.00 1 d . . .
N(1) N 0.1162(2) 0.4405(7) 0.5186(2) 0.0422(10) Uani 1.00 1 d . . .
C(1) C 0.5262(3) 0.3009(8) 0.5745(3) 0.0413(12) Uani 1.00 1 d . . .
C(2) C 0.4170(3) 0.3834(9) 0.5384(3) 0.0436(12) Uani 1.00 1 d . . .
C(3) C 0.3844(3) 0.5862(9) 0.4589(3) 0.0450(13) Uani 1.00 1 d . . .
C(4) C 0.0379(3) 0.3026(8) 0.4527(3) 0.0408(12) Uani 1.00 1 d . . .
C(5) C 0.0708(4) 0.0896(9) 0.4013(3) 0.0538(15) Uani 1.00 1 d . . .
C(6) C -0.0087(6) -0.0474(11) 0.3357(4) 0.071(2) Uani 1.00 1 d . . .
C(7) C -0.1245(6) 0.0101(11) 0.3158(4) 0.0712(19) Uani 1.00 1 d . . .
C(8) C -0.1612(4) 0.2102(10) 0.3631(3) 0.0579(15) Uani 1.00 1 d . . .
C(9) C -0.0810(3) 0.3628(9) 0.4333(3) 0.0423(12) Uani 1.00 1 d . . .
H(1) H 0.268(5) 0.381(12) 0.543(4) 0.09(2) Uiso 1.00 1 d . . .
H(2) H 0.1491 0.0440 0.4133 0.068 Uiso 1.00 1 c R . .
H(3) H 0.0147 -0.1889 0.3016 0.089 Uiso 1.00 1 c R . .
H(4) H -0.1784 -0.0915 0.2686 0.084 Uiso 1.00 1 c R . .
H(5) H -0.2405 0.2479 0.3492 0.066 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)
;
Br Br -0.290 2.459
;
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) 118.5(3) yes . . 3_566
Br(1) C(1) C(2) 120.4(3) yes . . .
Br(1) C(1) C(3) 118.5(2) yes . . 3_666
C(2) C(1) C(3) 121.1(4) yes . . 3_666
O(1) C(2) C(1) 122.0(4) yes . . .
O(1) C(2) C(3) 117.5(3) yes . . .
C(1) C(2) C(3) 120.5(4) yes . . .
O(2) C(3) C(1) 123.2(4) yes . . 3_666
O(2) C(3) C(2) 118.5(4) yes . . .
C(1) C(3) C(2) 118.4(3) yes 3_666 . .
N(1) C(4) C(5) 120.5(4) yes . . .
N(1) C(4) C(9) 121.0(4) yes . . .
C(5) C(4) C(9) 118.5(3) yes . . .
C(4) C(5) C(6) 119.8(5) yes . . .
C(5) C(6) C(7) 122.2(6) yes . . .
C(6) C(7) C(8) 120.6(5) yes . . .
C(7) C(8) C(9) 119.8(5) yes . . .
N(1) C(9) C(4) 120.5(3) yes 3_566 . .
N(1) C(9) C(8) 120.4(4) yes 3_566 . .
C(4) C(9) C(8) 119.0(4) yes . . .
C(2) O(1) H(1) 111(4) no . . .
C(4) C(5) H(2) 120.2 no . . .
C(6) C(5) H(2) 120.0 no . . .
C(5) C(6) H(3) 118.8 no . . .
C(7) C(6) H(3) 119.0 no . . .
C(6) C(7) H(4) 119.7 no . . .
C(8) C(7) H(4) 119.7 no . . .
C(7) C(8) H(5) 120.1 no . . .
C(9) C(8) H(5) 120.1 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
Br(1) C(1) 1.876(4) yes . .
O(1) C(2) 1.313(6) yes . .
O(2) C(3) 1.221(4) yes . .
N(1) C(4) 1.335(5) yes . .
N(1) C(9) 1.343(6) yes . 3_566
C(1) C(2) 1.347(5) yes . .
C(1) C(3) 1.449(6) yes . 3_666
C(2) C(3) 1.507(6) yes . .
C(4) C(5) 1.420(7) yes . .
C(4) C(9) 1.431(6) yes . .
C(5) C(6) 1.339(7) yes . .
C(6) C(7) 1.391(11) yes . .
C(7) C(8) 1.356(8) yes . .
C(8) C(9) 1.418(6) yes . .
O(1) H(1) 0.92(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) 2.670(4) ? . .
O(1) C(4) 3.551(4) ? . .
O(1) C(8) 3.568(6) ? . 3_556
O(1) C(8) 3.569(6) ? . 3_566
O(1) C(9) 3.535(5) ? . 3_566
O(2) N(1) 2.996(5) ? . .
O(2) C(4) 3.579(5) ? . .
O(2) C(5) 3.313(6) ? . 1_565
N(1) O(1) 2.670(4) ? . .
N(1) O(2) 2.996(5) ? . .
N(1) C(5) 3.554(6) ? . 1_565
N(1) C(6) 3.459(8) ? . 3_556
N(1) C(7) 3.294(7) ? . 3_556
N(1) C(8) 3.566(6) ? . 3_556
C(4) O(1) 3.551(4) ? . .
C(4) O(2) 3.579(5) ? . .
C(4) C(4) 3.494(6) ? . 3_556
C(4) C(5) 3.469(7) ? . 3_556
C(4) C(6) 3.555(7) ? . 1_565
C(4) C(6) 3.551(8) ? . 3_556
C(4) C(9) 3.600(6) ? . 3_556
C(5) O(2) 3.313(6) ? . 1_545
C(5) N(1) 3.554(6) ? . 1_545
C(5) C(4) 3.469(7) ? . 3_556
C(5) C(9) 3.294(7) ? . 3_556
C(6) N(1) 3.459(8) ? . 3_556
C(6) C(4) 3.555(7) ? . 1_545
C(6) C(4) 3.551(8) ? . 3_556
C(6) C(6) 3.594(9) ? . 2_545
C(6) C(6) 3.594(9) ? . 2_555
C(6) C(9) 3.439(8) ? . 1_545
C(7) N(1) 3.294(7) ? . 3_556
C(7) C(9) 3.547(7) ? . 1_545
C(8) O(1) 3.568(6) ? . 3_556
C(8) O(1) 3.569(6) ? . 3_566
C(8) N(1) 3.566(6) ? . 3_556
C(9) O(1) 3.535(5) ? . 3_566
C(9) C(4) 3.600(6) ? . 3_556
C(9) C(5) 3.294(7) ? . 3_556
C(9) C(6) 3.439(8) ? . 1_565
C(9) C(7) 3.547(7) ? . 1_565
Br(1) H(5) 3.146 ? . 4_655
O(1) H(2) 2.995 ? . .
O(1) H(5) 3.230 ? . 3_556
O(1) H(5) 2.949 ? . 3_566
O(2) H(2) 3.314 ? . .
O(2) H(2) 2.502 ? . 1_565
O(2) H(3) 3.369 ? . 1_565
O(2) H(4) 3.054 ? . 2_555
N(1) H(1) 1.81(6) ? . .
N(1) H(2) 3.396 ? . 1_565
N(1) H(4) 3.508 ? . 3_556
C(3) H(2) 3.534 ? . 1_565
C(4) H(1) 2.77(5) ? . .
C(4) H(3) 3.304 ? . 1_565
C(5) H(1) 3.05(5) ? . .
C(5) H(3) 3.121 ? . 2_555
C(5) H(4) 3.576 ? . 2_555
C(6) H(3) 2.687 ? . 2_555
C(7) H(3) 2.923 ? . 2_555
C(8) H(1) 2.96(7) ? . 3_566
C(8) H(2) 3.563 ? . 3_556
C(8) H(3) 3.526 ? . 2_555
C(9) H(1) 2.73(6) ? . 3_566
C(9) H(2) 3.334 ? . 3_556
C(9) H(3) 3.383 ? . 1_565
C(9) H(4) 3.570 ? . 1_565
H(1) N(1) 1.81(6) ? . .
H(1) C(4) 2.77(5) ? . .
H(1) C(5) 3.05(5) ? . .
H(1) C(8) 2.96(7) ? . 3_566
H(1) C(9) 2.73(6) ? . 3_566
H(1) H(2) 2.624 ? . .
H(1) H(5) 3.504 ? . 3_556
H(1) H(5) 2.512 ? . 3_566
H(2) O(1) 2.995 ? . .
H(2) O(2) 2.502 ? . 1_545
H(2) O(2) 3.314 ? . .
H(2) N(1) 3.396 ? . 1_545
H(2) C(3) 3.534 ? . 1_545
H(2) C(8) 3.563 ? . 3_556
H(2) C(9) 3.334 ? . 3_556
H(2) H(1) 2.624 ? . .
H(2) H(3) 3.514 ? . 2_555
H(2) H(4) 3.376 ? . 2_555
H(3) O(2) 3.369 ? . 1_545
H(3) C(4) 3.304 ? . 1_545
H(3) C(5) 3.121 ? . 2_545
H(3) C(6) 2.687 ? . 2_545
H(3) C(7) 2.923 ? . 2_545
H(3) C(8) 3.526 ? . 2_545
H(3) C(9) 3.383 ? . 1_545
H(3) H(2) 3.514 ? . 2_545
H(3) H(3) 2.833 ? . 2_545
H(3) H(3) 2.833 ? . 2_555
H(3) H(4) 3.199 ? . 2_545
H(4) O(2) 3.054 ? . 2_545
H(4) N(1) 3.508 ? . 3_556
H(4) C(5) 3.576 ? . 2_545
H(4) C(9) 3.570 ? . 1_545
H(4) H(2) 3.376 ? . 2_545
H(4) H(3) 3.199 ? . 2_555
H(4) H(5) 3.569 ? . 1_545
H(5) Br(1) 3.146 ? . 4_454
H(5) O(1) 3.230 ? . 3_556
H(5) O(1) 2.949 ? . 3_566
H(5) H(1) 3.504 ? . 3_556
H(5) H(1) 2.512 ? . 3_566
H(5) H(4) 3.569 ? . 1_565
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) . . . 2.697(5) 0.92(5) 2.24(7) 110(5) no
O(1) H(1) N(1) . . . 2.670(4) 0.92(5) 1.81(6) 155(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) -0.2(5) ? . . 3_566 3_566
C(4) N(1) C(9) C(8) -179.7(4) ? . . 3_566 3_566
C(9) N(1) C(4) C(5) -178.9(4) ? 3_566 . . .
C(9) N(1) C(4) C(9) 0.2(5) ? 3_566 . . .
Br(1) C(1) C(2) O(1) -0.6(6) ? . . . .
Br(1) C(1) C(2) C(3) -179.7(3) ? . . . .
Br(1) C(1) C(3) O(2) -0.8(6) ? . . 3_666 3_666
Br(1) C(1) C(3) C(2) 179.8(3) ? . . 3_666 3_666
C(2) C(1) C(3) O(2) 176.6(4) ? . . 3_666 3_666
C(2) C(1) C(3) C(2) -2.8(6) ? . . 3_666 3_666
C(3) C(1) C(2) O(1) -178.0(4) ? 3_666 . . .
C(3) C(1) C(2) C(3) 2.9(6) ? 3_666 . . .
O(1) C(2) C(3) O(2) -2.5(6) ? . . . .
O(1) C(2) C(3) C(1) 178.0(4) ? . . . 3_666
C(1) C(2) C(3) O(2) 176.7(4) ? . . . .
C(1) C(2) C(3) C(1) -2.8(6) ? . . . 3_666
N(1) C(4) C(5) C(6) 179.8(5) ? . . . .
N(1) C(4) C(9) N(1) -0.2(5) ? . . . 3_566
N(1) C(4) C(9) C(8) -179.7(4) ? . . . .
C(5) C(4) C(9) N(1) 178.9(4) ? . . . 3_566
C(5) C(4) C(9) C(8) -0.6(7) ? . . . .
C(9) C(4) C(5) C(6) 0.7(7) ? . . . .
C(4) C(5) C(6) C(7) -0.3(8) ? . . . .
C(5) C(6) C(7) C(8) -0.1(7) ? . . . .
C(6) C(7) C(8) C(9) 0.2(7) ? . . . .
C(7) C(8) C(9) N(1) -179.3(5) ? . . . 3_566
C(7) C(8) C(9) C(4) 0.2(6) ? . . . .
