#------------------------------------------------------------------------------
#$Date: 2019-12-03 07:27:02 +0200 (Tue, 03 Dec 2019) $
#$Revision: 244878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/96/7239618.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_7239618
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         'C18 H14 Br2 N2 O4'
_chemical_formula_sum            'C18 H14 Br2 N2 O4'
_chemical_formula_weight         482.13
_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                108.4731(13)
_cell_angle_beta                 91.2897(17)
_cell_angle_gamma                98.2241(15)
_cell_formula_units_Z            1
_cell_length_a                   4.8779(2)
_cell_length_b                   8.1042(3)
_cell_length_c                   11.8636(7)
_cell_measurement_reflns_used    2749
_cell_measurement_temperature    360
_cell_measurement_theta_max      67.72
_cell_measurement_theta_min      6.66
_cell_volume                     439.09(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    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      360
_diffrn_measured_fraction_theta_full 0.541
_diffrn_measured_fraction_theta_max 0.468
_diffrn_measurement_device_type  'IPDSC (Rigaku)'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.00000
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.541
_diffrn_reflns_Laue_measured_fraction_max 0.468
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1773
_diffrn_reflns_point_group_measured_fraction_full 0.541
_diffrn_reflns_point_group_measured_fraction_max 0.468
_diffrn_reflns_theta_full        36.870
_diffrn_reflns_theta_max         44.951
_diffrn_reflns_theta_min         7.163
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.807
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_crystal_colour            dark_red
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             238.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.52
_refine_ls_extinction_coef       0.083(5)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0476P)²+0.2932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1141
_reflns_number_total             1210
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c9ra06489c2.cif
_cod_data_source_block           H55dmbp-Hba_360K
_cod_database_code               7239618
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
Br1 Br 0.12332(14) 0.82400(5) 0.05630(4) 0.0623(4) Uani 1 1 d . .
O1 O 0.2872(8) 0.6074(3) 0.2137(2) 0.0623(14) Uani 1 1 d . .
H1 H 0.334610 0.546573 0.251975 0.075 Uiso 1 1 calc R U
O2 O 0.4111(8) 0.6537(4) -0.1669(2) 0.0564(14) Uani 1 1 d . .
N1 N 0.2992(8) 0.3755(4) 0.3623(2) 0.0470(15) Uani 1 1 d . .
C1 C 0.3760(10) 0.4313(3) 0.4785(2) 0.0395(17) Uani 1 1 d . .
C2 C 0.0789(11) 0.2512(4) 0.3176(3) 0.0520(19) Uani 1 1 d . .
H2 H 0.030595 0.216430 0.236213 0.062 Uiso 1 1 calc R U
C3 C -0.0815(10) 0.1712(4) 0.3865(3) 0.0441(18) Uani 1 1 d . .
C4 C -0.0054(11) 0.2310(5) 0.5066(3) 0.0537(19) Uani 1 1 d . .
H4 H -0.110555 0.184676 0.557127 0.064 Uiso 1 1 calc R U
C5 C 0.2249(11) 0.3590(4) 0.5539(3) 0.0504(18) Uani 1 1 d . .
H5 H 0.277386 0.395906 0.635019 0.061 Uiso 1 1 calc R U
C6 C -0.3248(13) 0.0291(5) 0.3289(4) 0.066(2) Uani 1 1 d . .
H6A H -0.454327 0.021175 0.387397 0.079 Uiso 1 1 calc R U
H6B H -0.260241 -0.081755 0.296462 0.079 Uiso 1 1 calc R U
H6C H -0.414715 0.057417 0.266125 0.079 Uiso 1 1 calc R U
C7 C 0.3806(10) 0.5613(4) 0.1125(2) 0.0437(18) Uani 1 1 d . .
C8 C 0.3350(10) 0.6403(4) 0.0248(3) 0.0390(17) Uani 1 1 d . .
C9 C 0.4487(10) 0.5855(4) -0.0847(2) 0.0422(18) 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 0.0074 0.0035
;
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 0.0135 0.0070
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0225 0.0128
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -2.1210 0.5893
;
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
C7 O1 H1 109.5 .
C1 N1 C2 120.9(2) .
N1 C1 C5 119.6(3) .
N1 C1 C1 117.9(3) 2_666
C5 C1 C1 122.5(3) 2_666
N1 C2 C3 123.1(3) .
N1 C2 H2 118.4 .
C3 C2 H2 118.4 .
C4 C3 C2 116.0(3) .
C4 C3 C6 124.0(3) .
C2 C3 C6 120.0(3) .
C3 C4 C5 121.3(3) .
C3 C4 H4 119.3 .
C5 C4 H4 119.3 .
C4 C5 C1 119.0(3) .
C4 C5 H5 120.5 .
C1 C5 H5 120.5 .
C3 C6 H6A 109.5 .
C3 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C3 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
O1 C7 C8 123.5(4) .
O1 C7 C9 117.6(3) 2_665
C8 C7 C9 118.8(3) 2_665
C9 C8 C7 120.7(4) .
C9 C8 Br1 119.2(3) .
C7 C8 Br1 120.1(2) .
O2 C9 C8 122.6(4) .
O2 C9 C7 117.0(3) 2_665
C8 C9 C7 120.4(3) 2_665
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C8 1.878(5) .
O1 C7 1.256(3) .
O1 H1 0.8200 .
O2 C9 1.286(5) .
N1 C1 1.333(4) .
N1 C2 1.333(5) .
C1 C5 1.388(4) .
C1 C1 1.480(6) 2_666
C2 C3 1.385(4) .
C2 H2 0.9300 .
C3 C4 1.375(5) .
C3 C6 1.509(5) .
C4 C5 1.387(5) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.412(6) .
C7 C9 1.505(7) 2_665
C8 C9 1.389(4) .
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 0.0(7) . .
C2 N1 C1 C1 179.5(5) . 2_666
C1 N1 C2 C3 -0.6(8) . .
N1 C2 C3 C4 1.7(8) . .
N1 C2 C3 C6 -178.9(5) . .
C2 C3 C4 C5 -2.3(8) . .
C6 C3 C4 C5 178.3(5) . .
C3 C4 C5 C1 1.9(8) . .
N1 C1 C5 C4 -0.7(8) . .
C1 C1 C5 C4 179.9(6) 2_666 .
O1 C7 C8 C9 178.8(4) . .
C9 C7 C8 C9 -0.9(6) 2_665 .
O1 C7 C8 Br1 -0.3(5) . .
C9 C7 C8 Br1 -180.0(2) 2_665 .
C7 C8 C9 O2 179.8(3) . .
Br1 C8 C9 O2 -1.2(5) . .
C7 C8 C9 C7 0.9(6) . 2_665
Br1 C8 C9 C7 180.0(2) . 2_665
