# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H22bpy-d8-Hia
_database_code_depnum_ccdc_archive 'CCDC 1944394'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H10 I2 N2 O4'
_chemical_formula_moiety         'C16 H10 I2 N2 O4'
_chemical_formula_weight         548.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.4936(15)
_cell_length_b                   9.6878(17)
_cell_length_c                   11.2320(19)
_cell_angle_alpha                102.855(2)
_cell_angle_beta                 100.7131(18)
_cell_angle_gamma                107.846(3)
_cell_volume                     824.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3010
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516.00
_exptl_absorpt_coefficient_mu    3.837
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.291
_exptl_absorpt_correction_T_max  0.681

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            13046
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         3.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3761
_reflns_number_gt                3356
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0664
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3761
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.98
_refine_diff_density_min         -1.06
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0751(15)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
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)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.26020(3) -0.28256(2) 0.10462(2) 0.04481(12) Uani 1 1 d . . . . .
I2 I 1.28507(3) 0.79359(2) 0.92228(2) 0.04553(12) Uani 1 1 d . . . . .
O1 O 0.0674(3) 0.0238(2) 0.25263(17) 0.0447(5) Uani 1 1 d . . . . .
O2 O 0.2561(3) 0.2361(2) 0.16940(19) 0.0545(6) Uani 1 1 d . . . . .
O3 O 0.9500(3) 0.5002(2) 0.75869(17) 0.0481(5) Uani 1 1 d . . . . .
O4 O 0.7350(3) 0.2725(2) 0.81407(18) 0.0457(5) Uani 1 1 d . . . . .
N1 N 0.2839(3) 0.2570(3) 0.4446(2) 0.0372(5) Uani 1 1 d . . . . .
N2 N 0.6835(3) 0.2157(3) 0.5669(2) 0.0392(6) Uani 1 1 d . . . . .
C1 C -0.1018(3) -0.1159(3) 0.0457(2) 0.0312(6) Uani 1 1 d . . . . .
C2 C 0.0293(3) 0.0049(3) 0.1311(2) 0.0334(6) Uani 1 1 d . . . . .
C3 C 0.1400(3) 0.1305(3) 0.0876(2) 0.0339(6) Uani 1 1 d . . . . .
C4 C 1.1170(3) 0.6223(3) 0.9705(2) 0.0307(5) Uani 1 1 d . . . . .
C5 C 0.9785(4) 0.5052(3) 0.8713(2) 0.0330(6) Uani 1 1 d . . . . .
C6 C 0.8588(3) 0.3775(3) 0.9063(2) 0.0325(6) Uani 1 1 d . . . . .
C7 C 0.1855(4) 0.3357(4) 0.4769(3) 0.0463(7) Uani 1 1 d . . . . .
H1 H 0.077706 0.310580 0.421998 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2375(4) 0.4523(3) 0.5884(3) 0.0477(8) Uani 1 1 d . . . . .
H2 H 0.165347 0.503157 0.610161 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4008(4) 0.4916(3) 0.6671(3) 0.0449(7) Uani 1 1 d . . . . .
H3 H 0.439929 0.569647 0.743141 0.054 Uiso 1 1 calc R U . . .
C10 C 0.5050(4) 0.4143(3) 0.6322(2) 0.0375(6) Uani 1 1 d . . . . .
H4 H 0.616171 0.441962 0.682928 0.045 Uiso 1 1 calc R U . . .
C11 C 0.4419(3) 0.2946(3) 0.5203(2) 0.0319(6) Uani 1 1 d . . . . .
C12 C 0.7853(4) 0.1403(4) 0.5342(3) 0.0480(7) Uani 1 1 d . . . . .
H5 H 0.881007 0.150269 0.596092 0.058 Uiso 1 1 calc R U . . .
C13 C 0.7543(4) 0.0493(3) 0.4135(3) 0.0456(8) Uani 1 1 d . . . . .
H6 H 0.827426 -0.001140 0.393247 0.055 Uiso 1 1 calc R U . . .
C14 C 0.6112(4) 0.0348(3) 0.3228(3) 0.0447(7) Uani 1 1 d . . . . .
H7 H 0.584845 -0.028127 0.240485 0.054 Uiso 1 1 calc R U . . .
C15 C 0.5079(4) 0.1138(3) 0.3545(2) 0.0427(7) Uani 1 1 d . . . . .
H8 H 0.412383 0.105921 0.293582 0.051 Uiso 1 1 calc R U . . .
C16 C 0.5476(3) 0.2054(3) 0.4783(2) 0.0316(6) Uani 1 1 d . . . . .
H9 H 0.184(5) 0.139(4) 0.296(3) 0.079(12) Uiso 1 1 d . . . . .
H10 H 0.763(5) 0.313(5) 0.720(4) 0.106(15) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.081(3) . ?
I2 C4 2.078(3) . ?
O1 C2 1.300(3) . ?
O1 H9 1.17(4) . ?
O2 C3 1.221(3) . ?
O3 C5 1.229(3) . ?
O4 C6 1.297(3) . ?
O4 H10 1.24(4) . ?
N1 C7 1.338(4) . ?
N1 C11 1.340(3) . ?
N2 C16 1.339(3) . ?
N2 C12 1.343(4) . ?
C1 C2 1.354(4) . ?
C1 C3 1.437(4) 2 ?
C2 C3 1.528(4) . ?
C4 C6 1.361(3) 2_767 ?
C4 C5 1.430(4) . ?
C5 C6 1.522(4) . ?
C7 C8 1.378(4) . ?
C7 H1 0.9300 . ?
C8 C9 1.386(4) . ?
C8 H2 0.9300 . ?
C9 C10 1.379(4) . ?
C9 H3 0.9300 . ?
C10 C11 1.390(3) . ?
C10 H4 0.9300 . ?
C11 C16 1.492(5) . ?
C12 C13 1.371(4) . ?
C12 H5 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H6 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H7 0.9300 . ?
C15 C16 1.389(3) . ?
C15 H8 0.9300 . ?

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
_geom_angle_publ_flag
C2 O1 H9 104.8(18) . . ?
C6 O4 H10 102(2) . . ?
C7 N1 C11 119.7(2) . . ?
C16 N2 C12 119.3(2) . . ?
C2 C1 C3 121.3(2) . 2 ?
C2 C1 I1 120.8(2) . . ?
C3 C1 I1 117.84(18) 2 . ?
O1 C2 C1 123.4(3) . . ?
O1 C2 C3 116.0(2) . . ?
C1 C2 C3 120.5(2) . . ?
O2 C3 C1 124.6(3) . 2 ?
O2 C3 C2 117.2(2) . . ?
C1 C3 C2 118.2(2) 2 . ?
C6 C4 C5 121.6(2) 2_767 . ?
C6 C4 I2 120.0(2) 2_767 . ?
C5 C4 I2 118.34(18) . . ?
O3 C5 C4 124.3(3) . . ?
O3 C5 C6 117.5(2) . . ?
C4 C5 C6 118.3(2) . . ?
O4 C6 C4 123.1(3) . 2_767 ?
O4 C6 C5 116.8(2) . . ?
C4 C6 C5 120.1(2) 2_767 . ?
N1 C7 C8 122.6(3) . . ?
N1 C7 H1 118.7 . . ?
C8 C7 H1 118.7 . . ?
C7 C8 C9 117.9(3) . . ?
C7 C8 H2 121.1 . . ?
C9 C8 H2 121.1 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H3 120.1 . . ?
C8 C9 H3 120.1 . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H4 120.4 . . ?
C11 C10 H4 120.4 . . ?
N1 C11 C10 120.8(3) . . ?
N1 C11 C16 117.4(2) . . ?
C10 C11 C16 121.7(3) . . ?
N2 C12 C13 122.8(3) . . ?
N2 C12 H5 118.6 . . ?
C13 C12 H5 118.6 . . ?
C12 C13 C14 118.0(3) . . ?
C12 C13 H6 121.0 . . ?
C14 C13 H6 121.0 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H7 120.1 . . ?
C13 C14 H7 120.1 . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H8 120.3 . . ?
C16 C15 H8 120.3 . . ?
N2 C16 C15 120.7(3) . . ?
N2 C16 C11 116.6(2) . . ?
C15 C16 C11 122.7(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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 O1 179.2(2) 2 . . . ?
I1 C1 C2 O1 1.4(4) . . . . ?
C3 C1 C2 C3 0.5(4) 2 . . . ?
I1 C1 C2 C3 -177.19(17) . . . . ?
O1 C2 C3 O2 1.3(4) . . . . ?
C1 C2 C3 O2 -180.0(3) . . . . ?
O1 C2 C3 C1 -179.2(2) . . . 2 ?
C1 C2 C3 C1 -0.5(4) . . . 2 ?
C6 C4 C5 O3 179.4(3) 2_767 . . . ?
I2 C4 C5 O3 -1.3(4) . . . . ?
C6 C4 C5 C6 -1.0(4) 2_767 . . . ?
I2 C4 C5 C6 178.24(17) . . . . ?
O3 C5 C6 O4 0.0(4) . . . . ?
C4 C5 C6 O4 -179.6(2) . . . . ?
O3 C5 C6 C4 -179.4(3) . . . 2_767 ?
C4 C5 C6 C4 1.0(4) . . . 2_767 ?
C11 N1 C7 C8 -2.2(4) . . . . ?
N1 C7 C8 C9 2.1(5) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 -2.2(4) . . . . ?
C7 N1 C11 C10 0.0(4) . . . . ?
C7 N1 C11 C16 -178.7(3) . . . . ?
C9 C10 C11 N1 2.2(4) . . . . ?
C9 C10 C11 C16 -179.2(3) . . . . ?
C16 N2 C12 C13 -1.6(4) . . . . ?
N2 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C15 1.7(4) . . . . ?
C13 C14 C15 C16 -1.0(4) . . . . ?
C12 N2 C16 C15 2.2(4) . . . . ?
C12 N2 C16 C11 -178.7(3) . . . . ?
C14 C15 C16 N2 -0.9(4) . . . . ?
C14 C15 C16 C11 -179.9(3) . . . . ?
N1 C11 C16 N2 -163.1(2) . . . . ?
C10 C11 C16 N2 18.2(4) . . . . ?
N1 C11 C16 C15 15.9(4) . . . . ?
C10 C11 C16 C15 -162.7(2) . . . . ?

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
O1 H9 O2 . . . 2.659(3) 1.17(3) 1.97(4) 114(2) no
O1 H9 N1 . . . 2.636(2) 1.17(3) 1.68(3) 134(3) no
O4 H10 O3 . . . 2.674(3) 1.24(5) 1.91(4) 115(2) no
O4 H10 N2 . . . 2.631(3) 1.24(5) 1.66(4) 129(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
# start Validation Reply Form
_vrf_PLAT355_H22bpy-d8-Hia       
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H9       .       1.17 Ang.  
RESPONSE: Essential observation of proton migration in the H-bonds.
;
_vrf_PLAT110_H22bpy-d8-Hia       
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT112_H22bpy-d8-Hia       
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT113_H22bpy-d8-Hia       
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: Essential observation near below the phase transition point.
;
# end Validation Reply Form
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_D55dmbp-Dba
_database_code_depnum_ccdc_archive 'CCDC 1944400'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H14 Br2 N2 O4'
_chemical_formula_moiety         'C18 H14 Br2 N2 O4'
_chemical_formula_weight         482.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.824(2)
_cell_length_b                   9.767(2)
_cell_length_c                   12.010(3)
_cell_angle_alpha                97.0170(16)
_cell_angle_beta                 104.879(3)
_cell_angle_gamma                115.300(3)
_cell_volume                     872.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2643
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476.00
_exptl_absorpt_coefficient_mu    4.689
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            13980
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         3.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3983
_reflns_number_gt                2997
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0863
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3983
_refine_ls_number_parameters     246
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0447P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.69
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0103(10)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
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)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.25694(4) -0.32145(3) 0.06482(3) 0.04915(13) Uani 1 1 d . . . . .
Br2 Br 1.27564(3) 0.82580(3) 0.94836(2) 0.04479(13) Uani 1 1 d . . . . .
O1 O 0.1206(2) -0.0472(2) 0.21723(15) 0.0444(4) Uani 1 1 d . . . . .
O2 O 0.3180(3) 0.2093(2) 0.16115(17) 0.0517(5) Uani 1 1 d . . . . .
O3 O 0.8995(2) 0.5575(2) 0.78931(14) 0.0470(5) Uani 1 1 d . . . . .
O4 O 0.6766(2) 0.2978(2) 0.83074(15) 0.0417(4) Uani 1 1 d . . . . .
N1 N 0.4732(3) 0.1226(2) 0.36514(17) 0.0367(5) Uani 1 1 d . . . . .
N2 N 0.5047(3) 0.3473(2) 0.64020(17) 0.0335(4) Uani 1 1 d . . . . .
C1 C -0.1087(3) -0.1376(3) 0.0314(2) 0.0328(5) Uani 1 1 d . . . . .
C2 C 0.0563(3) -0.0315(3) 0.1133(2) 0.0327(5) Uani 1 1 d . . . . .
C3 C 0.1725(3) 0.1155(3) 0.0834(2) 0.0332(5) Uani 1 1 d . . . . .
C4 C 1.1206(3) 0.6422(3) 0.9792(2) 0.0303(5) Uani 1 1 d . . . . .
C5 C 0.9511(3) 0.5374(3) 0.88782(19) 0.0316(5) Uani 1 1 d . . . . .
C6 C 0.8279(3) 0.3885(3) 0.91393(19) 0.0307(5) Uani 1 1 d . . . . .
C7 C 0.5581(3) 0.0590(3) 0.3196(2) 0.0400(6) Uani 1 1 d . . . . .
H1 H 0.506458 0.003610 0.239350 0.048 Uiso 1 1 calc R U . . .
C8 C 0.7191(3) 0.0710(3) 0.3851(2) 0.0363(6) Uani 1 1 d . . . . .
C9 C 0.7894(4) 0.1522(3) 0.5043(2) 0.0435(6) Uani 1 1 d . . . . .
H2 H 0.894767 0.159689 0.553098 0.052 Uiso 1 1 calc R U . . .
C10 C 0.7050(3) 0.2227(3) 0.5520(2) 0.0398(6) Uani 1 1 d . . . . .
H3 H 0.754889 0.279596 0.631789 0.048 Uiso 1 1 calc R U . . .
C11 C 0.5457(3) 0.2075(3) 0.47977(19) 0.0307(5) Uani 1 1 d . . . . .
C12 C 0.4282(3) 0.4218(3) 0.6843(2) 0.0351(5) Uani 1 1 d . . . . .
H4 H 0.469119 0.463726 0.766522 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2904(3) 0.4396(3) 0.6133(2) 0.0338(5) Uani 1 1 d . . . . .
C14 C 0.2351(3) 0.3768(3) 0.4912(2) 0.0397(6) Uani 1 1 d . . . . .
H5 H 0.143746 0.386796 0.439975 0.048 Uiso 1 1 calc R U . . .
C15 C 0.3143(3) 0.2993(3) 0.4446(2) 0.0346(5) Uani 1 1 d . . . . .
H6 H 0.276713 0.257478 0.362564 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4500(3) 0.2851(3) 0.52178(19) 0.0286(5) Uani 1 1 d . . . . .
C17 C 0.8091(4) -0.0022(3) 0.3272(3) 0.0531(7) Uani 1 1 d . . . . .
H7A H 0.721763 -0.085683 0.257718 0.064 Uiso 1 1 calc R U . . .
H8B H 0.865378 -0.043444 0.382820 0.064 Uiso 1 1 calc R U . . .
H9C H 0.897549 0.075988 0.304164 0.064 Uiso 1 1 calc R U . . .
C18 C 0.2083(4) 0.5231(3) 0.6701(3) 0.0489(7) Uani 1 1 d . . . . .
H10A H 0.299396 0.608166 0.737427 0.059 Uiso 1 1 calc R U . . .
H11B H 0.119418 0.450566 0.696325 0.059 Uiso 1 1 calc R U . . .
H12C H 0.153722 0.563537 0.612754 0.059 Uiso 1 1 calc R U . . .
H13 H 0.316(7) 0.072(5) 0.283(4) 0.168(18) Uiso 1 1 d . . . . .
H14 H 0.622(6) 0.345(5) 0.728(4) 0.154(17) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.880(2) . ?
Br2 C4 1.884(2) . ?
O1 C2 1.289(3) . ?
O2 C3 1.237(3) . ?
O3 C5 1.226(3) . ?
O4 C6 1.286(3) . ?
O4 H14 1.42(5) . ?
N1 C7 1.331(3) . ?
N1 C11 1.344(3) . ?
N1 H13 1.31(5) . ?
N2 C12 1.332(3) . ?
N2 C16 1.346(3) . ?
N2 H14 1.28(5) . ?
C1 C2 1.373(3) . ?
C1 C3 1.429(3) 2 ?
C2 C3 1.516(3) . ?
C4 C6 1.362(3) 2_767 ?
C4 C5 1.437(3) . ?
C5 C6 1.526(3) . ?
C7 C8 1.383(4) . ?
C7 H1 0.9300 . ?
C8 C9 1.382(4) . ?
C8 C17 1.508(3) . ?
C9 C10 1.384(4) . ?
C9 H2 0.9300 . ?
C10 C11 1.384(3) . ?
C10 H3 0.9300 . ?
C11 C16 1.489(4) . ?
C12 C13 1.385(3) . ?
C12 H4 0.9300 . ?
C13 C14 1.386(3) . ?
C13 C18 1.510(3) . ?
C14 C15 1.388(4) . ?
C14 H5 0.9300 . ?
C15 C16 1.384(3) . ?
C15 H6 0.9300 . ?
C17 H7A 0.9600 . ?
C17 H8B 0.9600 . ?
C17 H9C 0.9600 . ?
C18 H10A 0.9600 . ?
C18 H11B 0.9600 . ?
C18 H12C 0.9600 . ?

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
_geom_angle_publ_flag
C6 O4 H14 120.6(18) . . ?
C7 N1 C11 120.2(2) . . ?
C7 N1 H13 106.8(17) . . ?
C11 N1 H13 132.7(17) . . ?
C12 N2 C16 120.5(2) . . ?
C12 N2 H14 108.1(17) . . ?
C16 N2 H14 131.4(17) . . ?
C2 C1 C3 121.7(2) . 2 ?
C2 C1 Br1 120.97(18) . . ?
C3 C1 Br1 117.34(18) 2 . ?
O1 C2 C1 124.0(2) . . ?
O1 C2 C3 116.4(2) . . ?
C1 C2 C3 119.6(2) . . ?
O2 C3 C1 124.1(2) . 2 ?
O2 C3 C2 117.2(2) . . ?
C1 C3 C2 118.7(2) 2 . ?
C6 C4 C5 121.9(2) 2_767 . ?
C6 C4 Br2 119.57(18) 2_767 . ?
C5 C4 Br2 118.55(17) . . ?
O3 C5 C4 124.6(2) . . ?
O3 C5 C6 117.6(2) . . ?
C4 C5 C6 117.8(2) . . ?
O4 C6 C4 123.4(2) . 2_767 ?
O4 C6 C5 116.3(2) . . ?
C4 C6 C5 120.3(2) 2_767 . ?
N1 C7 C8 123.5(2) . . ?
N1 C7 H1 118.3 . . ?
C8 C7 H1 118.3 . . ?
C9 C8 C7 116.2(2) . . ?
C9 C8 C17 123.1(2) . . ?
C7 C8 C17 120.7(2) . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H2 119.6 . . ?
C10 C9 H2 119.6 . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H3 120.3 . . ?
C9 C10 H3 120.3 . . ?
N1 C11 C10 119.9(2) . . ?
N1 C11 C16 117.1(2) . . ?
C10 C11 C16 123.0(2) . . ?
N2 C12 C13 123.0(2) . . ?
N2 C12 H4 118.5 . . ?
C13 C12 H4 118.5 . . ?
C12 C13 C14 116.5(2) . . ?
C12 C13 C18 119.9(2) . . ?
C14 C13 C18 123.5(2) . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 H5 119.6 . . ?
C15 C14 H5 119.6 . . ?
C16 C15 C14 119.1(2) . . ?
C16 C15 H6 120.5 . . ?
C14 C15 H6 120.5 . . ?
N2 C16 C15 120.1(2) . . ?
N2 C16 C11 117.0(2) . . ?
C15 C16 C11 122.9(2) . . ?
C8 C17 H7A 109.5 . . ?
C8 C17 H8B 109.5 . . ?
H7A C17 H8B 109.5 . . ?
C8 C17 H9C 109.5 . . ?
H7A C17 H9C 109.5 . . ?
H8B C17 H9C 109.5 . . ?
C13 C18 H10A 109.5 . . ?
C13 C18 H11B 109.5 . . ?
H10A C18 H11B 109.5 . . ?
C13 C18 H12C 109.5 . . ?
H10A C18 H12C 109.5 . . ?
H11B C18 H12C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 O1 -179.1(2) 2 . . . ?
Br1 C1 C2 O1 -1.0(3) . . . . ?
C3 C1 C2 C3 1.8(4) 2 . . . ?
Br1 C1 C2 C3 179.94(16) . . . . ?
O1 C2 C3 O2 -0.9(3) . . . . ?
C1 C2 C3 O2 178.2(2) . . . . ?
O1 C2 C3 C1 179.1(2) . . . 2 ?
C1 C2 C3 C1 -1.7(4) . . . 2 ?
C6 C4 C5 O3 -178.4(2) 2_767 . . . ?
Br2 C4 C5 O3 0.9(3) . . . . ?
C6 C4 C5 C6 0.1(4) 2_767 . . . ?
Br2 C4 C5 C6 179.42(15) . . . . ?
O3 C5 C6 O4 -1.9(3) . . . . ?
C4 C5 C6 O4 179.4(2) . . . . ?
O3 C5 C6 C4 178.5(2) . . . 2_767 ?
C4 C5 C6 C4 -0.1(4) . . . 2_767 ?
C11 N1 C7 C8 1.9(4) . . . . ?
N1 C7 C8 C9 1.0(4) . . . . ?
N1 C7 C8 C17 -179.1(2) . . . . ?
C7 C8 C9 C10 -2.8(4) . . . . ?
C17 C8 C9 C10 177.4(2) . . . . ?
C8 C9 C10 C11 1.8(4) . . . . ?
C7 N1 C11 C10 -3.0(4) . . . . ?
C7 N1 C11 C16 175.4(2) . . . . ?
C9 C10 C11 N1 1.2(4) . . . . ?
C9 C10 C11 C16 -177.1(2) . . . . ?
C16 N2 C12 C13 0.2(4) . . . . ?
N2 C12 C13 C14 -0.7(3) . . . . ?
N2 C12 C13 C18 178.9(2) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C18 C13 C14 C15 -179.0(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C12 N2 C16 C15 0.5(3) . . . . ?
C12 N2 C16 C11 178.5(2) . . . . ?
C14 C15 C16 N2 -0.6(4) . . . . ?
C14 C15 C16 C11 -178.5(2) . . . . ?
N1 C11 C16 N2 169.06(16) . . . . ?
C10 C11 C16 N2 -12.6(4) . . . . ?
N1 C11 C16 C15 -13.1(4) . . . . ?
C10 C11 C16 C15 165.27(19) . . . . ?

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
O4 H14 O3 . . . 2.664(3) 1.42(5) 2.28(4) 89.0(18) no
N1 H13 O1 . . . 2.760(2) 1.31(5) 1.52(4) 153(4) no
N1 H13 O2 . . . 2.893(3) 1.31(5) 2.10(5) 114(3) no
N2 H14 O3 . . . 3.057(2) 1.28(5) 2.28(4) 115(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
# start Validation Reply Form
_vrf_PLAT353_D55dmbp-Dba         
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H13      .       1.32 Ang.  
RESPONSE: Essential observation of proton migration toward middle of H-bonds.
;
_vrf_PLAT771_D55dmbp-Dba         
;
PROBLEM: Suspect N-H Bond in CIF: N1       --H13       ..       1.31 Ang.  
RESPONSE: Essential observation of proton migration toward middle of H-bonds.
;
_vrf_PLAT110_D55dmbp-Dba         
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT112_D55dmbp-Dba         
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT113_D55dmbp-Dba         
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT482_D55dmbp-Dba         
;
PROBLEM: Small D-H..A Angle Rep for O4       ..O3       .      89.00 Degree
RESPONSE: ...
;
_vrf_PLAT772_D55dmbp-Dba         
;
PROBLEM: Suspect O-H Bond in CIF: O4       --H14       ..       1.42 Ang.  
RESPONSE: Essential observation of proton migration toward middle of H-bonds.
;
# end Validation Reply Form

#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_100K_D22bpy-Dia
_database_code_depnum_ccdc_archive 'CCDC 1944397'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H10 I2 N2 O4'
_chemical_formula_moiety         'C16 H10 I2 N2 O4'
_chemical_formula_weight         548.07
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_space_group_IT_number           1
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.3748(2)
_cell_length_b                   9.6561(2)
_cell_length_c                   11.1482(7)
_cell_angle_alpha                102.5857(7)
_cell_angle_beta                 100.6515(7)
_cell_angle_gamma                107.6011(7)
_cell_volume                     807.64(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    33023
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      72.14
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516.00
_exptl_absorpt_coefficient_mu    3.528
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68691
_diffrn_measurement_device_type  'IPDSC (Rigaku)'
_diffrn_reflns_number            12681
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         3.562
_diffrn_reflns_theta_full        24.340
_diffrn_measured_fraction_theta_max 0.673
_diffrn_measured_fraction_theta_full 0.743
_diffrn_reflns_Laue_measured_fraction_max 0.673
_diffrn_reflns_Laue_measured_fraction_full 0.743
_diffrn_reflns_point_group_measured_fraction_max 0.637
_diffrn_reflns_point_group_measured_fraction_full 0.709
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6647
_reflns_number_gt                6626
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.602
_reflns_Friedel_fraction_full    0.676

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0160
_refine_ls_R_factor_gt           0.0160
_refine_ls_wR_factor_ref         0.0441
_refine_ls_wR_factor_gt          0.0440
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6647
_refine_ls_number_parameters     433
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0306P)²+0.3119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 3064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.293(19)

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 -0.4929 1.7142
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.58199(2) 1.00928(3) 0.68402(2) 0.01802(13) Uani 1 1 d . . . . .
I2 I 0.01103(2) 0.41889(3) 0.84437(2) 0.01868(14) Uani 1 1 d . . . . .
I3 I 0.55956(2) 0.49927(3) 0.66132(2) 0.01869(14) Uani 1 1 d . . . . .
I4 I 0.03499(2) -0.07080(3) 0.87192(2) 0.01748(13) Uani 1 1 d . . . . .
O1 O 0.2426(5) 0.7123(6) 0.5195(3) 0.0178(12) Uani 1 1 d . . . . .
O2 O 0.0326(5) 0.4849(6) 0.5791(3) 0.0180(13) Uani 1 1 d . . . . .
H2A H 0.037406 0.501725 0.510649 0.022 Uiso 1 1 calc R U . . .
O3 O 0.3474(5) 0.7144(6) 1.0085(3) 0.0215(13) Uani 1 1 d . . . . .
O4 O 0.5621(5) 0.9428(7) 0.9512(3) 0.0212(14) Uani 1 1 d . . . . .
O5 O 0.0384(5) -0.0190(6) 0.5950(3) 0.0213(13) Uani 1 1 d . . . . .
O6 O 0.2343(5) 0.1927(6) 0.5127(3) 0.0197(13) Uani 1 1 d . . . . .
H6 H 0.151991 0.113343 0.474984 0.024 Uiso 1 1 calc R U . . .
O7 O 0.5464(5) 0.4583(6) 0.9384(3) 0.0238(14) Uani 1 1 d . . . . .
O8 O 0.3640(5) 0.2409(6) 1.0217(3) 0.0170(12) Uani 1 1 d . . . . .
N1 N 0.6062(5) 1.0046(7) 0.1924(3) 0.0167(13) Uani 1 1 d . . . . .
H1 H 0.583891 0.951017 0.114666 0.020 Uiso 1 1 calc R U . . .
N2 N 1.0084(5) 0.9552(7) 0.3160(3) 0.0194(15) Uani 1 1 d . . . . .
N3 N 0.5733(5) 0.4761(7) 0.2090(4) 0.0149(13) Uani 1 1 d . . . . .
H3A H 0.532461 0.401518 0.140059 0.018 Uiso 1 1 calc R U . . .
N4 N 0.9768(6) 0.4280(7) 0.3248(4) 0.0173(13) Uani 1 1 d . . . . .
C1 C 0.7442(6) 1.0083(8) 0.2799(4) 0.0129(13) Uani 1 1 d . . . . .
C2 C 0.5018(6) 1.0821(8) 0.2229(4) 0.0193(14) Uani 1 1 d . . . . .
H2 H 0.408012 1.076108 0.159847 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5329(9) 1.1701(13) 0.3463(7) 0.0202(16) Uani 1 1 d . . . . .
H3 H 0.461100 1.223093 0.367266 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6742(7) 1.1772(8) 0.4382(5) 0.0189(14) Uani 1 1 d . . . . .
H4 H 0.699046 1.236964 0.521716 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7791(6) 1.0951(8) 0.4058(4) 0.0184(15) Uani 1 1 d . . . . .
H5 H 0.872166 1.098284 0.467918 0.022 Uiso 1 1 calc R U . . .
C6 C 0.8484(6) 0.9187(8) 0.2364(4) 0.0154(14) Uani 1 1 d . . . . .
C7 C 1.1060(6) 0.8760(9) 0.2838(4) 0.0237(17) Uani 1 1 d . . . . .
H7 H 1.213840 0.899895 0.340227 0.028 Uiso 1 1 calc R U . . .
C8 C 1.0579(11) 0.7601(15) 0.1719(9) 0.0212(18) Uani 1 1 d . . . . .
H8 H 1.133367 0.711258 0.150715 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8911(7) 0.7191(8) 0.0916(4) 0.0173(15) Uani 1 1 d . . . . .
H9 H 0.852298 0.640027 0.016182 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7844(6) 0.7972(8) 0.1253(4) 0.0133(14) Uani 1 1 d . . . . .
H10 H 0.671682 0.768853 0.074598 0.016 Uiso 1 1 calc R U . . .
C11 C 0.7364(6) 0.5107(8) 0.2796(4) 0.0118(13) Uani 1 1 d . . . . .
C12 C 0.4714(6) 0.5544(8) 0.2427(4) 0.0144(14) Uani 1 1 d . . . . .
H12 H 0.360572 0.528812 0.189927 0.017 Uiso 1 1 calc R U . . .
C13 C 0.5309(11) 0.6728(15) 0.3555(9) 0.0185(15) Uani 1 1 d . . . . .
H13 H 0.460205 0.725469 0.380073 0.022 Uiso 1 1 calc R U . . .
C14 C 0.6972(7) 0.7100(9) 0.4297(4) 0.0194(16) Uani 1 1 d . . . . .
H14 H 0.739837 0.788121 0.505964 0.023 Uiso 1 1 calc R U . . .
C15 C 0.8019(6) 0.6310(8) 0.3907(4) 0.0191(16) Uani 1 1 d . . . . .
H15 H 0.915711 0.658948 0.439295 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8386(6) 0.4177(8) 0.2349(4) 0.0142(13) Uani 1 1 d . . . . .
C17 C 1.0768(6) 0.3524(8) 0.2923(4) 0.0198(15) Uani 1 1 d . . . . .
H17 H 1.174307 0.362762 0.354116 0.024 Uiso 1 1 calc R U . . .
C18 C 1.0436(7) 0.2579(12) 0.1700(6) 0.0199(16) Uani 1 1 d . . . . .
H18 H 1.118009 0.207238 0.149932 0.024 Uiso 1 1 calc R U . . .
C19 C 0.8959(7) 0.2412(9) 0.0783(5) 0.0201(15) Uani 1 1 d . . . . .
H19 H 0.866938 0.175571 -0.003466 0.024 Uiso 1 1 calc R U . . .
C20 C 0.7928(6) 0.3237(8) 0.1108(4) 0.0154(13) Uani 1 1 d . . . . .
H20 H 0.694987 0.316396 0.050866 0.018 Uiso 1 1 calc R U . . .
C21 C 0.2739(6) 0.7203(8) 0.6351(4) 0.0118(15) Uani 1 1 d . . . . .
C22 C 0.1584(6) 0.5953(9) 0.6726(4) 0.0147(16) Uani 1 1 d . . . . .
C23 C 0.1789(7) 0.5921(9) 0.7947(5) 0.0164(17) Uani 1 1 d . . . . .
C24 C 0.3174(7) 0.7117(9) 0.8965(4) 0.0182(17) Uani 1 1 d . . . . .
C25 C 0.4415(6) 0.8415(8) 0.8603(4) 0.0138(16) Uani 1 1 d . . . . .
C26 C 0.4127(7) 0.8380(9) 0.7326(4) 0.0132(16) Uani 1 1 d . . . . .
C27 C 0.1563(7) 0.0862(8) 0.6799(5) 0.0126(15) Uani 1 1 d . . . . .
C28 C 0.2673(6) 0.2110(9) 0.6375(4) 0.0124(15) Uani 1 1 d . . . . .
C29 C 0.3990(6) 0.3328(8) 0.7208(4) 0.0138(16) Uani 1 1 d . . . . .
C30 C 0.4341(6) 0.3489(9) 0.8567(5) 0.0171(17) Uani 1 1 d . . . . .
C31 C 0.3232(6) 0.2214(8) 0.9026(4) 0.0149(16) Uani 1 1 d . . . . .
C32 C 0.1931(7) 0.0974(9) 0.8119(4) 0.0157(17) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C26 2.072(6) . ?
I2 C23 2.086(6) . ?
I3 C29 2.078(6) . ?
I4 C32 2.083(6) . ?
O1 C21 1.247(5) . ?
O2 C22 1.328(6) . ?
O2 H2A 0.8200 . ?
O3 C24 1.220(5) . ?
O4 C25 1.263(6) . ?
O5 C27 1.238(6) . ?
O6 C28 1.328(5) . ?
O6 H6 0.8200 . ?
O7 C30 1.222(6) . ?
O8 C31 1.265(5) . ?
N1 C1 1.353(6) . ?
N1 C2 1.355(9) . ?
N1 H1 0.8600 . ?
N2 C7 1.322(10) . ?
N2 C6 1.358(6) . ?
N3 C11 1.345(6) . ?
N3 C12 1.351(9) . ?
N3 H3A 0.8600 . ?
N4 C17 1.315(10) . ?
N4 C16 1.346(6) . ?
C1 C5 1.395(7) . ?
C1 C6 1.475(8) . ?
C2 C3 1.381(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(10) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C10 1.392(7) . ?
C7 C8 1.380(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(10) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C15 1.386(8) . ?
C11 C16 1.488(8) . ?
C12 C13 1.391(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(11) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C20 1.389(7) . ?
C17 C18 1.391(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.393(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(10) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.421(7) . ?
C21 C22 1.494(9) . ?
C22 C23 1.348(6) . ?
C23 C24 1.449(7) . ?
C24 C25 1.550(9) . ?
C25 C26 1.391(6) . ?
C27 C32 1.419(6) . ?
C27 C28 1.508(9) . ?
C28 C29 1.350(8) . ?
C29 C30 1.454(6) . ?
C30 C31 1.548(9) . ?
C31 C32 1.385(7) . ?

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
_geom_angle_publ_flag
C22 O2 H2A 109.5 . . ?
C28 O6 H6 109.5 . . ?
C1 N1 C2 122.4(4) . . ?
C1 N1 H1 118.8 . . ?
C2 N1 H1 118.8 . . ?
C7 N2 C6 118.6(5) . . ?
C11 N3 C12 122.3(5) . . ?
C11 N3 H3A 118.8 . . ?
C12 N3 H3A 118.8 . . ?
C17 N4 C16 118.8(4) . . ?
N1 C1 C5 118.4(6) . . ?
N1 C1 C6 117.8(4) . . ?
C5 C1 C6 123.7(5) . . ?
N1 C2 C3 120.9(5) . . ?
N1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 118.2(7) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 120.2(6) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C1 119.8(5) . . ?
C4 C5 H5 120.1 . . ?
C1 C5 H5 120.1 . . ?
N2 C6 C10 121.2(6) . . ?
N2 C6 C1 115.9(5) . . ?
C10 C6 C1 122.8(4) . . ?
N2 C7 C8 124.1(6) . . ?
N2 C7 H7 117.9 . . ?
C8 C7 H7 117.9 . . ?
C7 C8 C9 117.4(8) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 H8 121.3 . . ?
C10 C9 C8 119.5(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C6 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C6 C10 H10 120.5 . . ?
N3 C11 C15 118.7(6) . . ?
N3 C11 C16 118.4(4) . . ?
C15 C11 C16 122.9(4) . . ?
N3 C12 C13 120.6(6) . . ?
N3 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 118.2(9) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 120.2(7) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C11 C15 C14 120.0(5) . . ?
C11 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N4 C16 C20 122.2(6) . . ?
N4 C16 C11 115.0(4) . . ?
C20 C16 C11 122.8(4) . . ?
N4 C17 C18 123.2(5) . . ?
N4 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C17 C18 C19 118.1(7) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C20 C19 C18 119.0(6) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C16 118.6(5) . . ?
C19 C20 H20 120.7 . . ?
C16 C20 H20 120.7 . . ?
O1 C21 C26 124.7(5) . . ?
O1 C21 C22 117.2(5) . . ?
C26 C21 C22 118.1(4) . . ?
O2 C22 C23 120.7(6) . . ?
O2 C22 C21 116.7(4) . . ?
C23 C22 C21 122.6(6) . . ?
C22 C23 C24 120.7(6) . . ?
C22 C23 I2 121.6(5) . . ?
C24 C23 I2 117.7(3) . . ?
O3 C24 C23 124.5(5) . . ?
O3 C24 C25 117.5(5) . . ?
C23 C24 C25 118.0(4) . . ?
O4 C25 C26 125.4(6) . . ?
O4 C25 C24 116.2(4) . . ?
C26 C25 C24 118.4(5) . . ?
C25 C26 C21 122.3(5) . . ?
C25 C26 I1 118.3(4) . . ?
C21 C26 I1 119.4(3) . . ?
O5 C27 C32 125.1(6) . . ?
O5 C27 C28 116.3(4) . . ?
C32 C27 C28 118.5(5) . . ?
O6 C28 C29 121.0(5) . . ?
O6 C28 C27 116.7(5) . . ?
C29 C28 C27 122.2(4) . . ?
C28 C29 C30 119.9(5) . . ?
C28 C29 I3 122.2(4) . . ?
C30 C29 I3 117.9(4) . . ?
O7 C30 C29 123.9(6) . . ?
O7 C30 C31 117.3(4) . . ?
C29 C30 C31 118.8(5) . . ?
O8 C31 C32 126.2(5) . . ?
O8 C31 C30 115.4(5) . . ?
C32 C31 C30 118.4(4) . . ?
C31 C32 C27 122.1(5) . . ?
C31 C32 I4 119.0(3) . . ?
C27 C32 I4 118.7(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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C5 0.1(8) . . . . ?
C2 N1 C1 C6 179.6(5) . . . . ?
C1 N1 C2 C3 0.3(10) . . . . ?
N1 C2 C3 C4 0.2(11) . . . . ?
C2 C3 C4 C5 -1.0(10) . . . . ?
C3 C4 C5 C1 1.5(9) . . . . ?
N1 C1 C5 C4 -1.0(9) . . . . ?
C6 C1 C5 C4 179.6(5) . . . . ?
C7 N2 C6 C10 2.3(8) . . . . ?
C7 N2 C6 C1 178.1(5) . . . . ?
N1 C1 C6 N2 163.4(5) . . . . ?
C5 C1 C6 N2 -17.2(7) . . . . ?
N1 C1 C6 C10 -20.9(7) . . . . ?
C5 C1 C6 C10 158.6(6) . . . . ?
C6 N2 C7 C8 1.9(10) . . . . ?
N2 C7 C8 C9 -3.8(13) . . . . ?
C7 C8 C9 C10 1.5(13) . . . . ?
C8 C9 C10 C6 2.4(10) . . . . ?
N2 C6 C10 C9 -4.4(8) . . . . ?
C1 C6 C10 C9 -180.0(5) . . . . ?
C12 N3 C11 C15 0.0(8) . . . . ?
C12 N3 C11 C16 179.9(5) . . . . ?
C11 N3 C12 C13 -1.9(10) . . . . ?
N3 C12 C13 C14 1.6(12) . . . . ?
C12 C13 C14 C15 0.6(13) . . . . ?
N3 C11 C15 C14 2.2(9) . . . . ?
C16 C11 C15 C14 -177.7(5) . . . . ?
C13 C14 C15 C11 -2.5(10) . . . . ?
C17 N4 C16 C20 3.5(9) . . . . ?
C17 N4 C16 C11 -178.2(5) . . . . ?
N3 C11 C16 N4 -161.7(6) . . . . ?
C15 C11 C16 N4 18.3(7) . . . . ?
N3 C11 C16 C20 16.6(7) . . . . ?
C15 C11 C16 C20 -163.5(6) . . . . ?
C16 N4 C17 C18 -2.2(10) . . . . ?
N4 C17 C18 C19 -0.9(11) . . . . ?
C17 C18 C19 C20 2.7(11) . . . . ?
C18 C19 C20 C16 -1.5(10) . . . . ?
N4 C16 C20 C19 -1.7(9) . . . . ?
C11 C16 C20 C19 -179.8(5) . . . . ?
O1 C21 C22 O2 0.7(9) . . . . ?
C26 C21 C22 O2 -178.4(5) . . . . ?
O1 C21 C22 C23 -179.6(6) . . . . ?
C26 C21 C22 C23 1.4(9) . . . . ?
O2 C22 C23 C24 179.3(7) . . . . ?
C21 C22 C23 C24 -0.5(10) . . . . ?
O2 C22 C23 I2 -1.9(9) . . . . ?
C21 C22 C23 I2 178.3(5) . . . . ?
C22 C23 C24 O3 -177.7(7) . . . . ?
I2 C23 C24 O3 3.5(10) . . . . ?
C22 C23 C24 C25 -0.7(10) . . . . ?
I2 C23 C24 C25 -179.5(5) . . . . ?
O3 C24 C25 O4 -1.9(10) . . . . ?
C23 C24 C25 O4 -179.1(6) . . . . ?
O3 C24 C25 C26 178.1(6) . . . . ?
C23 C24 C25 C26 0.9(9) . . . . ?
O4 C25 C26 C21 -179.9(8) . . . . ?
C24 C25 C26 C21 0.1(9) . . . . ?
O4 C25 C26 I1 1.2(9) . . . . ?
C24 C25 C26 I1 -178.7(5) . . . . ?
O1 C21 C26 C25 179.9(7) . . . . ?
C22 C21 C26 C25 -1.2(9) . . . . ?
O1 C21 C26 I1 -1.3(9) . . . . ?
C22 C21 C26 I1 177.7(5) . . . . ?
O5 C27 C28 O6 -3.4(9) . . . . ?
C32 C27 C28 O6 176.8(6) . . . . ?
O5 C27 C28 C29 179.3(6) . . . . ?
C32 C27 C28 C29 -0.5(9) . . . . ?
O6 C28 C29 C30 -179.0(6) . . . . ?
C27 C28 C29 C30 -1.8(9) . . . . ?
O6 C28 C29 I3 -0.3(9) . . . . ?
C27 C28 C29 I3 176.9(5) . . . . ?
C28 C29 C30 O7 -177.2(7) . . . . ?
I3 C29 C30 O7 4.1(9) . . . . ?
C28 C29 C30 C31 2.4(9) . . . . ?
I3 C29 C30 C31 -176.4(5) . . . . ?
O7 C30 C31 O8 -2.2(10) . . . . ?
C29 C30 C31 O8 178.2(6) . . . . ?
O7 C30 C31 C32 178.9(7) . . . . ?
C29 C30 C31 C32 -0.7(9) . . . . ?
O8 C31 C32 C27 179.6(7) . . . . ?
C30 C31 C32 C27 -1.6(10) . . . . ?
O8 C31 C32 I4 4.0(10) . . . . ?
C30 C31 C32 I4 -177.3(5) . . . . ?
O5 C27 C32 C31 -177.5(7) . . . . ?
C28 C27 C32 C31 2.2(9) . . . . ?
O5 C27 C32 I4 -1.8(10) . . . . ?
C28 C27 C32 I4 177.9(5) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

# start Validation Reply Form
_vrf_PLAT029_100K_D22bpy-Dia     
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.743 Why?  
RESPONSE: 
The data have been collected on 1-circle goniometer with IP area detector 
diffractometer. It is only the very high angle data that is incomplete due to 
the shape of the area detector, and we have ca. 100% coverage in the low angle 
data. This will always be a problem with area detector data that is not 
truncated. In addition, changing the direction of crystal is difficult 
due to the N2 blower for the temperaature control. The obtained 
analysis was sufficient to elucidate the molecular structure. 
;
_vrf_PLAT110_100K_D22bpy-Dia     
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE:
The crystal shows a symmetry reduction because of a few difference
due to the hydrogen bonding pattern.
;
_vrf_PLAT111_100K_D22bpy-Dia     
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: 
The crystal shows a symmetry reduction because of a few difference
due to the hydrogen bonding pattern.  From the fact that the system
shows ferroelectric property the reported space group (P1) is 
reasonable.
;
_vrf_PLAT112_100K_D22bpy-Dia     
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE:
The crystal shows a symmetry reduction because of a few difference
due to the hydrogen bonding pattern.  From the fact that the system
shows ferroelectric property the reported space group (P1) and
reported unit cell is reasonable.
;
_vrf_PLAT113_100K_D22bpy-Dia     
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE:
The crystal shows a symmetry reduction because of a few difference
due to the hydrogen bonding pattern.  From the fact that the system
shows ferroelectric property the reported space group (P1) is 
reasonable.
;
_vrf_PLAT911_100K_D22bpy-Dia     
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        608 Report
RESPONSE: 
A part of the data are missing by the blind area due to the cooling device. 
;
# end Validation Reply Form




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_D22bpy-Dia
_database_code_depnum_ccdc_archive 'CCDC 1944395'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H10 I2 N2 O4'
_chemical_formula_moiety         'C16 H10 I2 N2 O4'
_chemical_formula_weight         548.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.5223(19)
_cell_length_b                   9.665(2)
_cell_length_c                   11.255(3)
_cell_angle_alpha                102.807(3)
_cell_angle_beta                 100.659(2)
_cell_angle_gamma                107.876(3)
_cell_volume                     827.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3161
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    2.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516.00
_exptl_absorpt_coefficient_mu    3.824
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.250
_exptl_absorpt_correction_T_max  0.542

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            12790
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3762
_reflns_number_gt                3387
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0639
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0319P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.93
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0171(6)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
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)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.26191(2) -0.28366(2) 0.10301(2) 0.04552(10) Uani 1 1 d . . . . .
I2 I 1.28478(3) 0.79388(2) 0.92197(2) 0.04603(10) Uani 1 1 d . . . . .
O1 O 0.0660(3) 0.0228(2) 0.25188(16) 0.0450(5) Uani 1 1 d . . . . .
O2 O 0.2554(3) 0.2354(2) 0.16975(18) 0.0552(6) Uani 1 1 d . . . . .
O3 O 0.9501(3) 0.4994(2) 0.75877(16) 0.0489(5) Uani 1 1 d . . . . .
O4 O 0.7365(3) 0.2720(2) 0.81492(16) 0.0466(5) Uani 1 1 d . . . . .
N1 N 0.2858(3) 0.2574(2) 0.44519(19) 0.0373(5) Uani 1 1 d . . . . .
N2 N 0.6842(3) 0.2171(2) 0.56586(19) 0.0401(5) Uani 1 1 d . . . . .
C1 C -0.1027(3) -0.1161(3) 0.0448(2) 0.0328(5) Uani 1 1 d . . . . .
C2 C 0.0284(3) 0.0043(3) 0.1306(2) 0.0341(5) Uani 1 1 d . . . . .
C3 C 0.1396(3) 0.1300(3) 0.0880(2) 0.0355(6) Uani 1 1 d . . . . .
C4 C 1.1166(3) 0.6222(3) 0.9702(2) 0.0319(5) Uani 1 1 d . . . . .
C5 C 0.9786(3) 0.5049(3) 0.8713(2) 0.0325(5) Uani 1 1 d . . . . .
C6 C 0.8600(3) 0.3778(3) 0.9065(2) 0.0329(5) Uani 1 1 d . . . . .
C7 C 0.1875(4) 0.3373(3) 0.4779(3) 0.0475(7) Uani 1 1 d . . . . .
H1 H 0.080846 0.313520 0.422667 0.057 Uiso 1 1 calc R U . . .
C8 C 0.2386(4) 0.4517(3) 0.5888(2) 0.0471(8) Uani 1 1 d . . . . .
H2 H 0.166037 0.501573 0.611012 0.056 Uiso 1 1 calc R U . . .
C9 C 0.4013(4) 0.4917(3) 0.6677(3) 0.0440(7) Uani 1 1 d . . . . .
H3 H 0.440323 0.570245 0.743275 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5050(3) 0.4132(3) 0.6325(2) 0.0373(6) Uani 1 1 d . . . . .
H4 H 0.615206 0.439987 0.683473 0.045 Uiso 1 1 calc R U . . .
C11 C 0.4430(3) 0.2946(3) 0.5206(2) 0.0317(5) Uani 1 1 d . . . . .
C12 C 0.7855(4) 0.1405(3) 0.5327(3) 0.0492(7) Uani 1 1 d . . . . .
H5 H 0.880789 0.150166 0.594219 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7541(4) 0.0496(3) 0.4128(3) 0.0464(7) Uani 1 1 d . . . . .
H6 H 0.827851 0.000150 0.392481 0.056 Uiso 1 1 calc R U . . .
C14 C 0.6107(4) 0.0327(3) 0.3226(3) 0.0455(7) Uani 1 1 d . . . . .
H7 H 0.583557 -0.031576 0.240867 0.055 Uiso 1 1 calc R U . . .
C15 C 0.5076(4) 0.1128(3) 0.3552(2) 0.0428(6) Uani 1 1 d . . . . .
H8 H 0.412004 0.104847 0.294774 0.051 Uiso 1 1 calc R U . . .
C16 C 0.5475(3) 0.2047(3) 0.4783(2) 0.0313(5) Uani 1 1 d . . . . .
H9 H 0.181(4) 0.145(4) 0.292(3) 0.080(11) Uiso 1 1 d . . . . .
H10 H 0.762(4) 0.307(3) 0.718(3) 0.071(10) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.084(3) . ?
I2 C4 2.081(3) . ?
O1 C2 1.301(3) . ?
O1 H9 1.21(3) . ?
O2 C3 1.220(3) . ?
O3 C5 1.230(3) . ?
O4 C6 1.298(3) . ?
O4 H10 1.25(3) . ?
N1 C11 1.339(3) . ?
N1 C7 1.348(4) . ?
N2 C16 1.334(3) . ?
N2 C12 1.349(3) . ?
C1 C2 1.356(3) . ?
C1 C3 1.437(3) 2 ?
C2 C3 1.524(4) . ?
C4 C6 1.365(3) 2_767 ?
C4 C5 1.430(3) . ?
C5 C6 1.513(4) . ?
C7 C8 1.365(4) . ?
C7 H1 0.9300 . ?
C8 C9 1.386(4) . ?
C8 H2 0.9300 . ?
C9 C10 1.386(4) . ?
C9 H3 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H4 0.9300 . ?
C11 C16 1.491(4) . ?
C12 C13 1.364(4) . ?
C12 H5 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H6 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H7 0.9300 . ?
C15 C16 1.385(3) . ?
C15 H8 0.9300 . ?

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
_geom_angle_publ_flag
C2 O1 H9 101.8(15) . . ?
C6 O4 H10 103.7(15) . . ?
C11 N1 C7 119.6(2) . . ?
C16 N2 C12 119.1(2) . . ?
C2 C1 C3 121.4(2) . 2 ?
C2 C1 I1 120.69(19) . . ?
C3 C1 I1 117.92(18) 2 . ?
O1 C2 C1 123.7(2) . . ?
O1 C2 C3 115.8(2) . . ?
C1 C2 C3 120.4(2) . . ?
O2 C3 C1 124.4(3) . 2 ?
O2 C3 C2 117.4(2) . . ?
C1 C3 C2 118.2(2) 2 . ?
C6 C4 C5 121.5(2) 2_767 . ?
C6 C4 I2 120.15(19) 2_767 . ?
C5 C4 I2 118.35(17) . . ?
O3 C5 C4 124.5(2) . . ?
O3 C5 C6 117.4(2) . . ?
C4 C5 C6 118.1(2) . . ?
O4 C6 C4 122.6(2) . 2_767 ?
O4 C6 C5 117.0(2) . . ?
C4 C6 C5 120.4(2) 2_767 . ?
N1 C7 C8 122.5(3) . . ?
N1 C7 H1 118.7 . . ?
C8 C7 H1 118.7 . . ?
C7 C8 C9 118.5(3) . . ?
C7 C8 H2 120.8 . . ?
C9 C8 H2 120.8 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H3 120.4 . . ?
C8 C9 H3 120.4 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H4 120.3 . . ?
C11 C10 H4 120.3 . . ?
N1 C11 C10 120.7(2) . . ?
N1 C11 C16 117.3(2) . . ?
C10 C11 C16 122.0(2) . . ?
N2 C12 C13 122.8(3) . . ?
N2 C12 H5 118.6 . . ?
C13 C12 H5 118.6 . . ?
C12 C13 C14 118.5(3) . . ?
C12 C13 H6 120.8 . . ?
C14 C13 H6 120.8 . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 H7 120.5 . . ?
C15 C14 H7 120.5 . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H8 120.2 . . ?
C16 C15 H8 120.2 . . ?
N2 C16 C15 120.8(2) . . ?
N2 C16 C11 116.4(2) . . ?
C15 C16 C11 122.8(2) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 O1 179.3(2) 2 . . . ?
I1 C1 C2 O1 1.3(4) . . . . ?
C3 C1 C2 C3 0.7(4) 2 . . . ?
I1 C1 C2 C3 -177.33(17) . . . . ?
O1 C2 C3 O2 1.2(4) . . . . ?
C1 C2 C3 O2 179.9(3) . . . . ?
O1 C2 C3 C1 -179.4(2) . . . 2 ?
C1 C2 C3 C1 -0.7(4) . . . 2 ?
C6 C4 C5 O3 179.4(2) 2_767 . . . ?
I2 C4 C5 O3 -1.2(3) . . . . ?
C6 C4 C5 C6 -1.2(4) 2_767 . . . ?
I2 C4 C5 C6 178.16(16) . . . . ?
O3 C5 C6 O4 0.0(3) . . . . ?
C4 C5 C6 O4 -179.5(2) . . . . ?
O3 C5 C6 C4 -179.4(2) . . . 2_767 ?
C4 C5 C6 C4 1.2(4) . . . 2_767 ?
C11 N1 C7 C8 -3.1(4) . . . . ?
N1 C7 C8 C9 3.2(4) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C7 N1 C11 C10 0.7(4) . . . . ?
C7 N1 C11 C16 -178.6(2) . . . . ?
C9 C10 C11 N1 1.4(4) . . . . ?
C9 C10 C11 C16 -179.3(3) . . . . ?
C16 N2 C12 C13 -0.3(4) . . . . ?
N2 C12 C13 C14 -1.5(4) . . . . ?
C12 C13 C14 C15 2.5(4) . . . . ?
C13 C14 C15 C16 -1.8(4) . . . . ?
C12 N2 C16 C15 1.0(4) . . . . ?
C12 N2 C16 C11 -178.8(2) . . . . ?
C14 C15 C16 N2 0.0(4) . . . . ?
C14 C15 C16 C11 179.9(3) . . . . ?
N1 C11 C16 N2 -164.45(18) . . . . ?
C10 C11 C16 N2 16.3(4) . . . . ?
N1 C11 C16 C15 15.7(4) . . . . ?
C10 C11 C16 C15 -163.6(2) . . . . ?

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
O1 H9 O2 . . . 2.653(3) 1.21(3) 1.89(4) 116(2) no
O1 H9 N1 . . . 2.661(2) 1.21(3) 1.72(3) 130(3) no
O4 H10 O3 . . . 2.670(3) 1.25(4) 1.93(3) 112.1(17) no
O4 H10 N2 . . . 2.659(3) 1.25(4) 1.64(3) 133(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
# start Validation Reply Form
_vrf_PLAT355_D22bpy-Dia          
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H9       .       1.20 Ang.  
RESPONSE: Essential observation of proton migration in the H-bonds.
;
_vrf_PLAT110_D22bpy-Dia          
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT112_D22bpy-Dia          
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT113_D22bpy-Dia          
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT934_D22bpy-Dia          
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          2 Check 
RESPONSE: ...
;
# end Validation Reply Form
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H55dmbp-Hba_173K
_database_code_depnum_ccdc_archive 'CCDC 1944402'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H14 Br2 N2 O4'
_chemical_formula_moiety         'C18 H14 Br2 N2 O4'
_chemical_formula_weight         482.13
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_space_group_IT_number           1
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.8044(16)
_cell_length_b                   9.7839(17)
_cell_length_c                   11.882(2)
_cell_angle_alpha                97.226(2)
_cell_angle_beta                 104.520(2)
_cell_angle_gamma                115.868(3)
_cell_volume                     858.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2796
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476.00
_exptl_absorpt_coefficient_mu    4.763
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            14035
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7435
_reflns_number_gt                6485
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_max     0.884
_reflns_Friedel_fraction_full    0.907

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0562
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         7435
_refine_ls_number_parameters     490
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0241P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.63
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0102(6)
_refine_ls_abs_structure_details 
;
 Flack x determined using 2688 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.454(16)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
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)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.16273(7) -0.28902(6) 0.65922(6) 0.0245(3) Uani 1 1 d . . . . .
Br2 Br 0.34541(7) 0.36001(6) 0.52423(5) 0.0242(4) Uani 1 1 d . . . . .
Br3 Br -0.18334(7) 0.20648(6) 0.64392(5) 0.0232(3) Uani 1 1 d . . . . .
Br4 Br 0.37155(7) 0.86611(6) 0.54194(6) 0.0237(3) Uani 1 1 d . . . . .
O1 O 0.2180(8) -0.0127(7) 0.8087(5) 0.0233(14) Uani 1 1 d . . . . .
O2 O 0.4078(8) 0.2473(7) 0.7532(6) 0.0252(15) Uani 1 1 d . . . . .
O3 O -0.0355(7) 0.0774(7) 0.3681(5) 0.0212(13) Uani 1 1 d . . . . .
O4 O -0.2317(8) -0.1801(7) 0.4331(6) 0.0264(16) Uani 1 1 d . . . . .
O5 O 0.1950(8) 0.4807(7) 0.8048(5) 0.0241(14) Uani 1 1 d . . . . .
O6 O 0.4229(8) 0.7396(7) 0.7612(6) 0.0210(14) Uani 1 1 d . . . . .
O7 O -0.0108(8) 0.5978(7) 0.3808(5) 0.0265(14) Uani 1 1 d . . . . .
O8 O -0.2322(8) 0.3324(7) 0.4221(6) 0.0223(15) Uani 1 1 d . . . . .
N1 N 0.5666(9) 0.1555(8) 0.9603(6) 0.0186(15) Uani 1 1 d . . . . .
N2 N 0.5958(9) 0.3834(8) 1.2356(6) 0.0177(15) Uani 1 1 d . . . . .
N3 N 0.5929(9) 0.6915(8) 0.9528(6) 0.0169(15) Uani 1 1 d . . . . .
N4 N 0.6281(9) 0.9230(8) 1.2297(6) 0.0175(16) Uani 1 1 d . . . . .
C1 C -0.0151(11) -0.1031(9) 0.6230(8) 0.0147(18) Uani 1 1 d . . . . .
C2 C 0.1490(12) 0.0027(10) 0.7039(8) 0.0198(18) Uani 1 1 d . . . . .
C3 C 0.2655(11) 0.1536(9) 0.6745(8) 0.0180(18) Uani 1 1 d . . . . .
C4 C 0.1974(11) 0.1721(10) 0.5552(8) 0.0182(19) Uani 1 1 d . . . . .
C5 C 0.0323(11) 0.0647(9) 0.4747(8) 0.0149(16) Uani 1 1 d . . . . .
C6 C -0.0839(11) -0.0826(10) 0.5085(8) 0.0180(17) Uani 1 1 d . . . . .
C7 C -0.0281(11) 0.3923(9) 0.6119(8) 0.0158(18) Uani 1 1 d . . . . .
C8 C 0.1401(11) 0.4981(10) 0.7045(8) 0.0174(17) Uani 1 1 d . . . . .
C9 C 0.2651(11) 0.6469(9) 0.6766(8) 0.0155(17) Uani 1 1 d . . . . .
C10 C 0.2137(11) 0.6796(9) 0.5701(8) 0.0150(18) Uani 1 1 d . . . . .
C11 C 0.0399(11) 0.5746(9) 0.4785(8) 0.0152(17) Uani 1 1 d . . . . .
C12 C -0.0828(10) 0.4233(9) 0.5045(8) 0.0158(17) Uani 1 1 d . . . . .
C13 C 0.6534(11) 0.0924(9) 0.9131(8) 0.0198(18) Uani 1 1 d . . . . .
H5 H 0.600676 0.033944 0.830618 0.024 Uiso 1 1 calc R U . . .
C14 C 0.8172(11) 0.1102(9) 0.9811(8) 0.0205(18) Uani 1 1 d . . . . .
C15 C 0.8901(12) 0.1941(10) 1.0992(8) 0.0229(19) Uani 1 1 d . . . . .
H6 H 1.000331 0.205524 1.148649 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8037(12) 0.2637(10) 1.1482(8) 0.0212(18) Uani 1 1 d . . . . .
H7 H 0.854997 0.323518 1.230337 0.025 Uiso 1 1 calc R U . . .
C17 C 0.6429(10) 0.2441(8) 1.0754(7) 0.0162(17) Uani 1 1 d . . . . .
C18 C 0.5450(10) 0.3208(9) 1.1157(7) 0.0176(18) Uani 1 1 d . . . . .
C19 C 0.4136(12) 0.3391(10) 1.0376(8) 0.021(2) Uani 1 1 d . . . . .
H8 H 0.377800 0.298127 0.952911 0.026 Uiso 1 1 calc R U . . .
C20 C 0.3346(11) 0.4173(10) 1.0835(8) 0.024(2) Uani 1 1 d . . . . .
H9 H 0.244628 0.429851 1.029547 0.029 Uiso 1 1 calc R U . . .
C21 C 0.3846(11) 0.4779(9) 1.2072(8) 0.0207(18) Uani 1 1 d . . . . .
C22 C 0.5196(10) 0.4583(9) 1.2787(8) 0.0187(18) Uani 1 1 d . . . . .
H10 H 0.560159 0.500944 1.363628 0.022 Uiso 1 1 calc R U . . .
C23 C 0.9065(12) 0.0374(10) 0.9194(8) 0.029(2) Uani 1 1 d . . . . .
H11A H 0.959581 0.102093 0.868734 0.034 Uiso 1 1 calc R U . . .
H12B H 0.816596 -0.069417 0.869036 0.034 Uiso 1 1 calc R U . . .
H13C H 1.000786 0.032685 0.980644 0.034 Uiso 1 1 calc R U . . .
C24 C 0.3025(12) 0.5644(10) 1.2611(8) 0.026(2) Uani 1 1 d . . . . .
H14A H 0.392707 0.645545 1.335306 0.031 Uiso 1 1 calc R U . . .
H15B H 0.200489 0.489584 1.279924 0.031 Uiso 1 1 calc R U . . .
H16C H 0.260941 0.614316 1.203162 0.031 Uiso 1 1 calc R U . . .
C25 C 0.6654(11) 0.6119(10) 0.9069(8) 0.0193(18) Uani 1 1 d . . . . .
H17 H 0.621154 0.565835 0.822315 0.023 Uiso 1 1 calc R U . . .
C26 C 0.8034(10) 0.5953(9) 0.9801(7) 0.0170(17) Uani 1 1 d . . . . .
C27 C 0.8607(10) 0.6588(9) 1.1033(8) 0.0182(18) Uani 1 1 d . . . . .
H18 H 0.954128 0.648847 1.155765 0.022 Uiso 1 1 calc R U . . .
C28 C 0.7821(11) 0.7375(9) 1.1509(8) 0.0175(18) Uani 1 1 d . . . . .
H19 H 0.819538 0.779834 1.235567 0.021 Uiso 1 1 calc R U . . .
C29 C 0.6477(10) 0.7530(8) 1.0721(7) 0.0154(17) Uani 1 1 d . . . . .
C30 C 0.5527(10) 0.8305(9) 1.1165(7) 0.0169(17) Uani 1 1 d . . . . .
C31 C 0.3864(11) 0.8053(10) 1.0448(8) 0.0229(19) Uani 1 1 d . . . . .
H20 H 0.332084 0.740290 0.964214 0.028 Uiso 1 1 calc R U . . .
C32 C 0.3007(11) 0.8753(10) 1.0915(8) 0.025(2) Uani 1 1 d . . . . .
H21 H 0.190374 0.862841 1.041289 0.030 Uiso 1 1 calc R U . . .
C33 C 0.3754(11) 0.9645(9) 1.2122(8) 0.0205(17) Uani 1 1 d . . . . .
C34 C 0.5437(11) 0.9861(10) 1.2762(8) 0.0218(18) Uani 1 1 d . . . . .
H22 H 0.601142 1.049345 1.357449 0.026 Uiso 1 1 calc R U . . .
C35 C 0.8792(12) 0.5080(10) 0.9195(8) 0.026(2) Uani 1 1 d . . . . .
H23A H 0.928624 0.562440 0.862893 0.031 Uiso 1 1 calc R U . . .
H24B H 0.783643 0.400124 0.875526 0.031 Uiso 1 1 calc R U . . .
H25C H 0.974689 0.504590 0.980761 0.031 Uiso 1 1 calc R U . . .
C36 C 0.2821(12) 1.0362(10) 1.2685(9) 0.032(2) Uani 1 1 d . . . . .
H26A H 0.363503 1.106249 1.348933 0.038 Uiso 1 1 calc R U . . .
H27B H 0.174162 0.952129 1.275366 0.038 Uiso 1 1 calc R U . . .
H28C H 0.248071 1.096795 1.217659 0.038 Uiso 1 1 calc R U . . .
H1 H 0.342(6) 0.071(5) 0.848(4) 0.018(11) Uiso 1 1 d . . . . .
H2 H 0.454(6) 0.706(5) 0.821(4) 0.016(12) Uiso 1 1 d . . . . .
H3 H 0.665(6) 0.372(5) 1.284(4) 0.022(14) Uiso 1 1 d . . . . .
H4 H 0.718(7) 0.944(6) 1.267(4) 0.026(15) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.897(8) . ?
Br2 C4 1.880(9) . ?
Br3 C7 1.893(8) . ?
Br4 C10 1.883(8) . ?
O1 C2 1.299(11) . ?
O1 H1 0.97(5) . ?
O2 C3 1.216(10) . ?
O3 C5 1.304(11) . ?
O4 C6 1.234(10) . ?
O5 C8 1.232(10) . ?
O6 C9 1.317(10) . ?
O6 H2 0.85(5) . ?
O7 C11 1.221(11) . ?
O8 C12 1.263(10) . ?
N1 C17 1.344(9) . ?
N1 C13 1.348(10) . ?
N2 C22 1.326(10) . ?
N2 C18 1.352(10) . ?
N2 H3 0.78(5) . ?
N3 C29 1.339(10) . ?
N3 C25 1.346(10) . ?
N4 C34 1.325(10) . ?
N4 C30 1.338(10) . ?
N4 H4 0.73(5) . ?
C1 C2 1.354(12) . ?
C1 C6 1.421(12) . ?
C2 C3 1.531(13) . ?
C3 C4 1.461(12) . ?
C4 C5 1.360(11) . ?
C5 C6 1.533(13) . ?
C7 C12 1.367(12) . ?
C7 C8 1.426(12) . ?
C8 C9 1.532(12) . ?
C9 C10 1.361(12) . ?
C10 C11 1.447(11) . ?
C11 C12 1.531(12) . ?
C13 C14 1.387(11) . ?
C13 H5 0.9500 . ?
C14 C15 1.362(11) . ?
C14 C23 1.520(11) . ?
C15 C16 1.398(11) . ?
C15 H6 0.9500 . ?
C16 C17 1.377(12) . ?
C16 H7 0.9500 . ?
C17 C18 1.489(8) . ?
C18 C19 1.383(12) . ?
C19 C20 1.385(12) . ?
C19 H8 0.9500 . ?
C20 C21 1.391(12) . ?
C20 H9 0.9500 . ?
C21 C22 1.380(12) . ?
C21 C24 1.510(11) . ?
C22 H10 0.9500 . ?
C23 H11A 0.9800 . ?
C23 H12B 0.9800 . ?
C23 H13C 0.9800 . ?
C24 H14A 0.9800 . ?
C24 H15B 0.9800 . ?
C24 H16C 0.9800 . ?
C25 C26 1.392(11) . ?
C25 H17 0.9500 . ?
C26 C27 1.382(11) . ?
C26 C35 1.509(11) . ?
C27 C28 1.395(11) . ?
C27 H18 0.9500 . ?
C28 C29 1.391(12) . ?
C28 H19 0.9500 . ?
C29 C30 1.493(8) . ?
C30 C31 1.392(12) . ?
C31 C32 1.382(12) . ?
C31 H20 0.9500 . ?
C32 C33 1.401(12) . ?
C32 H21 0.9500 . ?
C33 C34 1.393(12) . ?
C33 C36 1.508(12) . ?
C34 H22 0.9500 . ?
C35 H23A 0.9800 . ?
C35 H24B 0.9800 . ?
C35 H25C 0.9800 . ?
C36 H26A 0.9800 . ?
C36 H27B 0.9800 . ?
C36 H28C 0.9800 . ?

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
_geom_angle_publ_flag
C2 O1 H1 111(3) . . ?
C9 O6 H2 118(3) . . ?
C17 N1 C13 119.7(7) . . ?
C22 N2 C18 121.1(7) . . ?
C22 N2 H3 116(3) . . ?
C18 N2 H3 122(3) . . ?
C29 N3 C25 120.5(7) . . ?
C34 N4 C30 121.1(7) . . ?
C34 N4 H4 117(4) . . ?
C30 N4 H4 122(4) . . ?
C2 C1 C6 122.6(8) . . ?
C2 C1 Br1 120.2(7) . . ?
C6 C1 Br1 117.2(6) . . ?
O1 C2 C1 124.6(9) . . ?
O1 C2 C3 115.7(8) . . ?
C1 C2 C3 119.7(9) . . ?
O2 C3 C4 125.9(8) . . ?
O2 C3 C2 116.5(9) . . ?
C4 C3 C2 117.6(8) . . ?
C5 C4 C3 122.0(8) . . ?
C5 C4 Br2 122.1(7) . . ?
C3 C4 Br2 115.8(6) . . ?
O3 C5 C4 124.2(8) . . ?
O3 C5 C6 116.6(7) . . ?
C4 C5 C6 119.1(9) . . ?
O4 C6 C1 123.1(8) . . ?
O4 C6 C5 118.1(9) . . ?
C1 C6 C5 118.9(7) . . ?
C12 C7 C8 122.6(8) . . ?
C12 C7 Br3 119.6(6) . . ?
C8 C7 Br3 117.7(7) . . ?
O5 C8 C7 126.1(8) . . ?
O5 C8 C9 116.8(7) . . ?
C7 C8 C9 117.1(8) . . ?
O6 C9 C10 122.7(8) . . ?
O6 C9 C8 116.2(8) . . ?
C10 C9 C8 121.1(8) . . ?
C9 C10 C11 121.4(8) . . ?
C9 C10 Br4 119.2(6) . . ?
C11 C10 Br4 119.4(7) . . ?
O7 C11 C10 123.6(8) . . ?
O7 C11 C12 118.8(7) . . ?
C10 C11 C12 117.6(8) . . ?
O8 C12 C7 123.7(8) . . ?
O8 C12 C11 116.2(8) . . ?
C7 C12 C11 120.1(7) . . ?
N1 C13 C14 122.1(8) . . ?
N1 C13 H5 118.9 . . ?
C14 C13 H5 119.0 . . ?
C15 C14 C13 118.0(7) . . ?
C15 C14 C23 123.7(8) . . ?
C13 C14 C23 118.3(8) . . ?
C14 C15 C16 120.4(8) . . ?
C14 C15 H6 119.8 . . ?
C16 C15 H6 119.8 . . ?
C17 C16 C15 118.8(8) . . ?
C17 C16 H7 120.6 . . ?
C15 C16 H7 120.6 . . ?
N1 C17 C16 120.9(7) . . ?
N1 C17 C18 115.6(6) . . ?
C16 C17 C18 123.4(6) . . ?
N2 C18 C19 118.7(7) . . ?
N2 C18 C17 117.3(6) . . ?
C19 C18 C17 123.9(7) . . ?
C18 C19 C20 119.7(8) . . ?
C18 C19 H8 120.1 . . ?
C20 C19 H8 120.1 . . ?
C19 C20 C21 121.1(9) . . ?
C19 C20 H9 119.5 . . ?
C21 C20 H9 119.4 . . ?
C22 C21 C20 115.6(8) . . ?
C22 C21 C24 121.5(8) . . ?
C20 C21 C24 122.9(8) . . ?
N2 C22 C21 123.7(8) . . ?
N2 C22 H10 118.2 . . ?
C21 C22 H10 118.1 . . ?
C14 C23 H11A 109.5 . . ?
C14 C23 H12B 109.4 . . ?
H11A C23 H12B 109.5 . . ?
C14 C23 H13C 109.5 . . ?
H11A C23 H13C 109.5 . . ?
H12B C23 H13C 109.5 . . ?
C21 C24 H14A 109.4 . . ?
C21 C24 H15B 109.5 . . ?
H14A C24 H15B 109.5 . . ?
C21 C24 H16C 109.5 . . ?
H14A C24 H16C 109.5 . . ?
H15B C24 H16C 109.5 . . ?
N3 C25 C26 121.8(8) . . ?
N3 C25 H17 119.1 . . ?
C26 C25 H17 119.1 . . ?
C27 C26 C25 117.8(7) . . ?
C27 C26 C35 124.5(8) . . ?
C25 C26 C35 117.7(8) . . ?
C26 C27 C28 120.3(8) . . ?
C26 C27 H18 119.9 . . ?
C28 C27 H18 119.8 . . ?
C29 C28 C27 118.8(8) . . ?
C29 C28 H19 120.6 . . ?
C27 C28 H19 120.6 . . ?
N3 C29 C28 120.7(7) . . ?
N3 C29 C30 117.4(6) . . ?
C28 C29 C30 121.8(6) . . ?
N4 C30 C31 119.5(7) . . ?
N4 C30 C29 118.7(6) . . ?
C31 C30 C29 121.8(7) . . ?
C32 C31 C30 119.7(8) . . ?
C32 C31 H20 120.1 . . ?
C30 C31 H20 120.1 . . ?
C31 C32 C33 120.5(8) . . ?
C31 C32 H21 119.8 . . ?
C33 C32 H21 119.7 . . ?
C34 C33 C32 115.6(8) . . ?
C34 C33 C36 122.1(8) . . ?
C32 C33 C36 122.3(8) . . ?
N4 C34 C33 123.5(8) . . ?
N4 C34 H22 118.3 . . ?
C33 C34 H22 118.2 . . ?
C26 C35 H23A 109.4 . . ?
C26 C35 H24B 109.5 . . ?
H23A C35 H24B 109.5 . . ?
C26 C35 H25C 109.5 . . ?
H23A C35 H25C 109.5 . . ?
H24B C35 H25C 109.5 . . ?
C33 C36 H26A 109.5 . . ?
C33 C36 H27B 109.4 . . ?
H26A C36 H27B 109.5 . . ?
C33 C36 H28C 109.5 . . ?
H26A C36 H28C 109.5 . . ?
H27B C36 H28C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -179.0(9) . . . . ?
Br1 C1 C2 O1 0.3(12) . . . . ?
C6 C1 C2 C3 1.7(11) . . . . ?
Br1 C1 C2 C3 -178.9(6) . . . . ?
O1 C2 C3 O2 -2.7(12) . . . . ?
C1 C2 C3 O2 176.6(8) . . . . ?
O1 C2 C3 C4 176.9(7) . . . . ?
C1 C2 C3 C4 -3.8(11) . . . . ?
O2 C3 C4 C5 -176.7(9) . . . . ?
C2 C3 C4 C5 3.8(11) . . . . ?
O2 C3 C4 Br2 -0.7(12) . . . . ?
C2 C3 C4 Br2 179.7(6) . . . . ?
C3 C4 C5 O3 178.7(8) . . . . ?
Br2 C4 C5 O3 3.0(12) . . . . ?
C3 C4 C5 C6 -1.7(11) . . . . ?
Br2 C4 C5 C6 -177.4(6) . . . . ?
C2 C1 C6 O4 178.3(9) . . . . ?
Br1 C1 C6 O4 -1.0(12) . . . . ?
C2 C1 C6 C5 0.4(11) . . . . ?
Br1 C1 C6 C5 -179.0(6) . . . . ?
O3 C5 C6 O4 1.1(12) . . . . ?
C4 C5 C6 O4 -178.5(8) . . . . ?
O3 C5 C6 C1 179.1(7) . . . . ?
C4 C5 C6 C1 -0.5(11) . . . . ?
C12 C7 C8 O5 177.0(9) . . . . ?
Br3 C7 C8 O5 -0.3(12) . . . . ?
C12 C7 C8 C9 -3.3(11) . . . . ?
Br3 C7 C8 C9 179.3(6) . . . . ?
O5 C8 C9 O6 2.5(12) . . . . ?
C7 C8 C9 O6 -177.1(7) . . . . ?
O5 C8 C9 C10 -177.4(7) . . . . ?
C7 C8 C9 C10 2.9(11) . . . . ?
O6 C9 C10 C11 179.4(8) . . . . ?
C8 C9 C10 C11 -0.6(11) . . . . ?
O6 C9 C10 Br4 -0.9(11) . . . . ?
C8 C9 C10 Br4 179.0(6) . . . . ?
C9 C10 C11 O7 -178.7(9) . . . . ?
Br4 C10 C11 O7 1.6(11) . . . . ?
C9 C10 C11 C12 -1.2(10) . . . . ?
Br4 C10 C11 C12 179.1(6) . . . . ?
C8 C7 C12 O8 -178.9(8) . . . . ?
Br3 C7 C12 O8 -1.6(12) . . . . ?
C8 C7 C12 C11 1.5(12) . . . . ?
Br3 C7 C12 C11 178.8(6) . . . . ?
O7 C11 C12 O8 -1.1(13) . . . . ?
C10 C11 C12 O8 -178.7(7) . . . . ?
O7 C11 C12 C7 178.5(8) . . . . ?
C10 C11 C12 C7 0.9(11) . . . . ?
C17 N1 C13 C14 2.8(12) . . . . ?
N1 C13 C14 C15 0.1(12) . . . . ?
N1 C13 C14 C23 -178.9(8) . . . . ?
C13 C14 C15 C16 -1.9(13) . . . . ?
C23 C14 C15 C16 177.0(9) . . . . ?
C14 C15 C16 C17 0.8(13) . . . . ?
C13 N1 C17 C16 -3.9(12) . . . . ?
C13 N1 C17 C18 174.5(7) . . . . ?
C15 C16 C17 N1 2.2(13) . . . . ?
C15 C16 C17 C18 -176.1(7) . . . . ?
C22 N2 C18 C19 1.4(12) . . . . ?
C22 N2 C18 C17 177.8(6) . . . . ?
N1 C17 C18 N2 166.8(8) . . . . ?
C16 C17 C18 N2 -14.8(10) . . . . ?
N1 C17 C18 C19 -17.0(10) . . . . ?
C16 C17 C18 C19 161.3(10) . . . . ?
N2 C18 C19 C20 -1.4(12) . . . . ?
C17 C18 C19 C20 -177.6(7) . . . . ?
C18 C19 C20 C21 -0.1(13) . . . . ?
C19 C20 C21 C22 1.7(12) . . . . ?
C19 C20 C21 C24 179.8(8) . . . . ?
C18 N2 C22 C21 0.3(12) . . . . ?
C20 C21 C22 N2 -1.9(11) . . . . ?
C24 C21 C22 N2 -180.0(8) . . . . ?
C29 N3 C25 C26 -2.4(12) . . . . ?
N3 C25 C26 C27 2.2(11) . . . . ?
N3 C25 C26 C35 -178.2(8) . . . . ?
C25 C26 C27 C28 -0.4(11) . . . . ?
C35 C26 C27 C28 -180.0(8) . . . . ?
C26 C27 C28 C29 -1.1(12) . . . . ?
C25 N3 C29 C28 0.8(11) . . . . ?
C25 N3 C29 C30 -176.1(6) . . . . ?
C27 C28 C29 N3 1.0(12) . . . . ?
C27 C28 C29 C30 177.7(6) . . . . ?
C34 N4 C30 C31 2.7(13) . . . . ?
C34 N4 C30 C29 -175.4(7) . . . . ?
N3 C29 C30 N4 -165.1(8) . . . . ?
C28 C29 C30 N4 18.0(10) . . . . ?
N3 C29 C30 C31 16.8(9) . . . . ?
C28 C29 C30 C31 -160.1(10) . . . . ?
N4 C30 C31 C32 -0.4(13) . . . . ?
C29 C30 C31 C32 177.7(7) . . . . ?
C30 C31 C32 C33 -3.4(13) . . . . ?
C31 C32 C33 C34 4.7(12) . . . . ?
C31 C32 C33 C36 -176.9(9) . . . . ?
C30 N4 C34 C33 -1.3(13) . . . . ?
C32 C33 C34 N4 -2.4(12) . . . . ?
C36 C33 C34 N4 179.2(8) . . . . ?

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
O1 H1 O2 . . . 2.639(9) 0.97(4) 2.13(5) 111(4) no
O1 H1 N1 . . . 2.730(8) 0.97(4) 1.83(4) 152(5) no
O6 H2 O5 . . . 2.670(9) 0.85(5) 2.32(4) 105(3) no
O6 H2 N3 . . . 2.611(10) 0.85(5) 1.79(5) 160(4) no
N2 H3 O7 . . 1_656 3.021(8) 0.78(6) 2.56(4) 119(4) no
N2 H3 O8 . . 1_656 2.590(11) 0.78(6) 1.84(5) 160(6) no
N4 H4 O3 . . 1_666 2.605(8) 0.73(5) 1.92(4) 158(6) no
N4 H4 O4 . . 1_666 2.931(11) 0.73(5) 2.49(6) 121(5) no

# start Validation Reply Form
_vrf_PLAT110_H55dmbp-Hba_173K    
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Essential observations in the vicinity of the phase transitions.
;
_vrf_PLAT111_H55dmbp-Hba_173K    
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: Symmetry is actually broken as evidenced by ferroelectricity.
;
_vrf_PLAT112_H55dmbp-Hba_173K    
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: Essential observations in the vicinity of the phase transitions. 
;
_vrf_PLAT113_H55dmbp-Hba_173K    
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: Symmetry is actually broken as evidenced by ferroelectricity.
;
# end Validation Reply Form
#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_anrt_D22bpy-Dia
_database_code_depnum_ccdc_archive 'CCDC 1944399'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H10 I2 N2 O4'
_chemical_formula_moiety         'C16 H10 I2 N2 O4'
_chemical_formula_weight         548.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.5359(2)
_cell_length_b                   9.6656(2)
_cell_length_c                   11.2585(7)
_cell_angle_alpha                102.8436(7)
_cell_angle_beta                 100.6667(7)
_cell_angle_gamma                107.8250(7)
_cell_volume                     829.48(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18896
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      45.77
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516.00
_exptl_absorpt_coefficient_mu    3.443
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68750
_diffrn_measurement_device_type  'IPDSC (Rigaku)'
_diffrn_reflns_number            15309
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_theta_max         34.996
_diffrn_reflns_theta_min         2.520
_diffrn_reflns_theta_full        24.362
_diffrn_measured_fraction_theta_max 0.569
_diffrn_measured_fraction_theta_full 0.724
_diffrn_reflns_Laue_measured_fraction_max 0.569
_diffrn_reflns_Laue_measured_fraction_full 0.724
_diffrn_reflns_point_group_measured_fraction_max 0.569
_diffrn_reflns_point_group_measured_fraction_full 0.724
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4586
_reflns_number_gt                4090
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0790
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0456P)²+0.2959P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.82
_refine_diff_density_min         -1.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


# start Validation Reply Form
_vrf_PLAT029_anrt_D22bpy-Dia     
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.724 Why?  
RESPONSE:
The data have been collected on 1-circle goniometer with IP area detector 
diffractometer. It is only the very high angle data that is incomplete due to 
the shape of the area detector, and we have ca. 100% coverage in the low angle 
data. This will always be a problem with area detector data that is not 
truncated. The obtained analysis was sufficient to elucidate the molecular 
structure. 
;
_vrf_PLAT110_anrt_D22bpy-Dia     
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: 
The crystal shows a symmetry reduction because of a few difference
due to the hydrogen bonding pattern.
;
_vrf_PLAT112_anrt_D22bpy-Dia     
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: 
The crystal shows a symmetry reduction because of a few difference
due to the hydrogen bonding pattern.
;
_vrf_PLAT113_anrt_D22bpy-Dia     
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: 
The crystal shows a symmetry reduction because of a few difference
due to the hydrogen bonding pattern.
;
_vrf_PLAT911_anrt_D22bpy-Dia     
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        788 Report
RESPONSE: 
A part of the data are missing by the blind area due to the cooling device. 
;
# end Validation Reply Form




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_375K_D22bpy-Dia
_database_code_depnum_ccdc_archive 'CCDC 1944398'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H10 I2 N2 O4'
_chemical_formula_moiety         'C16 H10 I2 N2 O4'
_chemical_formula_weight         548.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.8002(3)
_cell_length_b                   8.5129(5)
_cell_length_c                   11.2407(7)
_cell_angle_alpha                102.1304(9)
_cell_angle_beta                 101.7257(10)
_cell_angle_gamma                104.5226(11)
_cell_volume                     418.54(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4465
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      38.70
_cell_measurement_temperature    375
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             258.00
_exptl_absorpt_coefficient_mu    3.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      375
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68750
_diffrn_measurement_device_type  'IPDSC (Rigaku)'
_diffrn_reflns_number            3497
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_full        24.362
_diffrn_measured_fraction_theta_max 0.668
_diffrn_measured_fraction_theta_full 0.744
_diffrn_reflns_Laue_measured_fraction_max 0.668
_diffrn_reflns_Laue_measured_fraction_full 0.744
_diffrn_reflns_point_group_measured_fraction_max 0.668
_diffrn_reflns_point_group_measured_fraction_full 0.744
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1798
_reflns_number_gt                1672
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.1066
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         1798
_refine_ls_number_parameters     130
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0611P)²+0.1931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.83
_refine_diff_density_min         -0.77
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.266(13)

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)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

# start Validation Reply Form
_vrf_PLAT029_375K_D22bpy-Dia     
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.744 Why?  
RESPONSE:
The data have been collected on 1-circle goniometer with IP area detector 
diffractometer. It is only the very high angle data that is incomplete due to 
the shape of the area detector, and we have ca. 100% coverage in the low angle 
data. This will always be a problem with area detector data that is not 
truncated. In addition, changing the direction of crystal is difficult 
due to the N2 blower for the temperaature control. The obtained 
analysis was sufficient to elucidate the molecular structure. 
;
_vrf_PLAT305_375K_D22bpy-Dia     
;
PROBLEM: Isolated Hydrogen Atom   (Outside Bond Range ??)         H5 Check 
RESPONSE:
The hydrogen atom has bifurcated hydrogen bond between two oxygen 
atoms and a nitrogen atom in this phase. This is essential 
quality for this compound.  
;
_vrf_PLAT430_375K_D22bpy-Dia     
;
PROBLEM: Short Inter D...A Contact  O1       ..N1       .       2.84 Ang.  
RESPONSE: 
The two molecules are connected strong hydrogen bond.  This is 
essential quality for this compound.  
;
_vrf_PLAT772_375K_D22bpy-Dia     
;
PROBLEM: Suspect O-H Bond in CIF: O1       --H5        ..       1.42 Ang.  
RESPONSE: 
The hydrogen atom has bifurcated hydrogen bond between two oxygen 
atoms and a nitrogen atom in this phase. 
;
_vrf_PLAT911_375K_D22bpy-Dia     
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        389 Report
RESPONSE:
A part of the data are missing by the blind area due to the cooling device. 
;
# end Validation Reply Form




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H55dmbp-Hba_RT
_database_code_depnum_ccdc_archive 'CCDC 1944401'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H14 Br2 N2 O4'
_chemical_formula_moiety         'C18 H14 Br2 N2 O4'
_chemical_formula_weight         482.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.812(3)
_cell_length_b                   9.795(3)
_cell_length_c                   11.993(3)
_cell_angle_alpha                97.0435(19)
_cell_angle_beta                 105.051(4)
_cell_angle_gamma                115.222(4)
_cell_volume                     871.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2484
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476.00
_exptl_absorpt_coefficient_mu    4.692
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.289
_exptl_absorpt_correction_T_max  0.829

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            13734
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         3.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3977
_reflns_number_gt                3096
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0883
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3977
_refine_ls_number_parameters     246
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0430P)²+0.2174P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.78
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0070(9)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
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)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.25324(4) -0.31941(3) 0.06734(3) 0.04912(13) Uani 1 1 d . . . . .
Br2 Br 1.27561(4) 0.82528(3) 0.94903(3) 0.04521(13) Uani 1 1 d . . . . .
O1 O 0.1236(3) -0.0451(2) 0.21901(17) 0.0446(5) Uani 1 1 d . . . . .
O2 O 0.3182(3) 0.2112(2) 0.15994(18) 0.0515(5) Uani 1 1 d . . . . .
O3 O 0.8984(3) 0.5576(2) 0.78898(16) 0.0478(5) Uani 1 1 d . . . . .
O4 O 0.6755(3) 0.2972(2) 0.82971(17) 0.0425(5) Uani 1 1 d . . . . .
N1 N 0.4709(3) 0.1203(3) 0.36558(19) 0.0368(5) Uani 1 1 d . . . . .
N2 N 0.5039(3) 0.3458(2) 0.64136(18) 0.0329(5) Uani 1 1 d . . . . .
C1 C -0.1069(3) -0.1365(3) 0.0327(2) 0.0334(5) Uani 1 1 d . . . . .
C2 C 0.0578(3) -0.0302(3) 0.1139(2) 0.0332(5) Uani 1 1 d . . . . .
C3 C 0.1729(3) 0.1159(3) 0.0833(2) 0.0346(6) Uani 1 1 d . . . . .
C4 C 1.1201(3) 0.6419(3) 0.9795(2) 0.0313(5) Uani 1 1 d . . . . .
C5 C 0.9508(3) 0.5371(3) 0.8873(2) 0.0327(5) Uani 1 1 d . . . . .
C6 C 0.8280(3) 0.3886(3) 0.9137(2) 0.0322(5) Uani 1 1 d . . . . .
C7 C 0.5563(4) 0.0572(3) 0.3203(2) 0.0400(6) Uani 1 1 d . . . . .
H1 H 0.503548 0.000321 0.240186 0.048 Uiso 1 1 calc R U . . .
C8 C 0.7193(4) 0.0716(3) 0.3857(3) 0.0380(6) Uani 1 1 d . . . . .
C9 C 0.7919(4) 0.1549(3) 0.5046(3) 0.0425(7) Uani 1 1 d . . . . .
H2 H 0.898683 0.163950 0.553252 0.051 Uiso 1 1 calc R U . . .
C10 C 0.7072(3) 0.2250(3) 0.5523(2) 0.0395(6) Uani 1 1 d . . . . .
H3 H 0.758353 0.283436 0.631862 0.047 Uiso 1 1 calc R U . . .
C11 C 0.5454(3) 0.2072(3) 0.4800(2) 0.0314(5) Uani 1 1 d . . . . .
C12 C 0.4281(3) 0.4216(3) 0.6846(2) 0.0365(6) Uani 1 1 d . . . . .
H4 H 0.469305 0.463797 0.767011 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2913(4) 0.4408(3) 0.6134(2) 0.0359(6) Uani 1 1 d . . . . .
C14 C 0.2362(3) 0.3785(3) 0.4907(2) 0.0381(6) Uani 1 1 d . . . . .
H5 H 0.145422 0.389066 0.438972 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3153(3) 0.3007(3) 0.4447(2) 0.0347(6) Uani 1 1 d . . . . .
H6 H 0.278395 0.259714 0.362484 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4498(3) 0.2846(3) 0.5222(2) 0.0298(5) Uani 1 1 d . . . . .
C17 C 0.8099(4) 0.0003(4) 0.3277(3) 0.0540(8) Uani 1 1 d . . . . .
H7A H 0.722447 -0.083547 0.258197 0.065 Uiso 1 1 calc R U . . .
H8B H 0.867991 -0.039800 0.383429 0.065 Uiso 1 1 calc R U . . .
H9C H 0.897166 0.078621 0.304193 0.065 Uiso 1 1 calc R U . . .
C18 C 0.2105(4) 0.5249(4) 0.6700(3) 0.0474(7) Uani 1 1 d . . . . .
H10A H 0.302783 0.611359 0.736171 0.057 Uiso 1 1 calc R U . . .
H11B H 0.123590 0.453933 0.698170 0.057 Uiso 1 1 calc R U . . .
H12C H 0.153404 0.563047 0.611807 0.057 Uiso 1 1 calc R U . . .
H13 H 0.270(8) 0.056(7) 0.266(5) 0.18(2) Uiso 1 1 d . . . . .
H14 H 0.643(7) 0.343(6) 0.748(5) 0.17(2) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.881(3) . ?
Br2 C4 1.887(3) . ?
O1 C2 1.298(3) . ?
O1 H13 1.16(6) . ?
O2 C3 1.231(3) . ?
O3 C5 1.223(3) . ?
O4 C6 1.293(3) . ?
O4 H14 1.14(6) . ?
N1 C7 1.331(3) . ?
N1 C11 1.345(3) . ?
N2 C12 1.332(3) . ?
N2 C16 1.350(3) . ?
C1 C2 1.367(3) . ?
C1 C3 1.436(4) 2 ?
C2 C3 1.516(4) . ?
C4 C6 1.358(4) 2_767 ?
C4 C5 1.436(3) . ?
C5 C6 1.529(4) . ?
C7 C8 1.384(4) . ?
C7 H1 0.9300 . ?
C8 C9 1.380(4) . ?
C8 C17 1.501(4) . ?
C9 C10 1.384(4) . ?
C9 H2 0.9300 . ?
C10 C11 1.387(3) . ?
C10 H3 0.9300 . ?
C11 C16 1.487(4) . ?
C12 C13 1.384(4) . ?
C12 H4 0.9300 . ?
C13 C14 1.389(4) . ?
C13 C18 1.504(4) . ?
C14 C15 1.385(4) . ?
C14 H5 0.9300 . ?
C15 C16 1.384(3) . ?
C15 H6 0.9300 . ?
C17 H7A 0.9600 . ?
C17 H8B 0.9600 . ?
C17 H9C 0.9600 . ?
C18 H10A 0.9600 . ?
C18 H11B 0.9600 . ?
C18 H12C 0.9600 . ?

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
_geom_angle_publ_flag
C2 O1 H13 110(3) . . ?
C6 O4 H14 116(3) . . ?
C7 N1 C11 119.9(2) . . ?
C12 N2 C16 120.2(2) . . ?
C2 C1 C3 121.7(2) . 2 ?
C2 C1 Br1 121.0(2) . . ?
C3 C1 Br1 117.35(19) 2 . ?
O1 C2 C1 123.7(2) . . ?
O1 C2 C3 116.5(2) . . ?
C1 C2 C3 119.7(2) . . ?
O2 C3 C1 123.5(2) . 2 ?
O2 C3 C2 117.9(2) . . ?
C1 C3 C2 118.6(2) 2 . ?
C6 C4 C5 122.1(2) 2_767 . ?
C6 C4 Br2 119.46(19) 2_767 . ?
C5 C4 Br2 118.48(19) . . ?
O3 C5 C4 124.8(2) . . ?
O3 C5 C6 117.7(2) . . ?
C4 C5 C6 117.5(2) . . ?
O4 C6 C4 123.3(2) . 2_767 ?
O4 C6 C5 116.2(2) . . ?
C4 C6 C5 120.5(2) 2_767 . ?
N1 C7 C8 123.6(2) . . ?
N1 C7 H1 118.2 . . ?
C8 C7 H1 118.2 . . ?
C9 C8 C7 116.4(2) . . ?
C9 C8 C17 123.0(3) . . ?
C7 C8 C17 120.6(3) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H2 119.7 . . ?
C10 C9 H2 119.7 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H3 120.3 . . ?
C11 C10 H3 120.3 . . ?
N1 C11 C10 120.0(2) . . ?
N1 C11 C16 117.2(2) . . ?
C10 C11 C16 122.8(2) . . ?
N2 C12 C13 123.5(2) . . ?
N2 C12 H4 118.3 . . ?
C13 C12 H4 118.3 . . ?
C12 C13 C14 116.4(2) . . ?
C12 C13 C18 120.0(3) . . ?
C14 C13 C18 123.7(3) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H5 119.7 . . ?
C13 C14 H5 119.7 . . ?
C16 C15 C14 119.5(2) . . ?
C16 C15 H6 120.3 . . ?
C14 C15 H6 120.3 . . ?
N2 C16 C15 119.9(2) . . ?
N2 C16 C11 117.2(2) . . ?
C15 C16 C11 122.8(2) . . ?
C8 C17 H7A 109.5 . . ?
C8 C17 H8B 109.5 . . ?
H7A C17 H8B 109.5 . . ?
C8 C17 H9C 109.5 . . ?
H7A C17 H9C 109.5 . . ?
H8B C17 H9C 109.5 . . ?
C13 C18 H10A 109.5 . . ?
C13 C18 H11B 109.5 . . ?
H10A C18 H11B 109.5 . . ?
C13 C18 H12C 109.5 . . ?
H10A C18 H12C 109.5 . . ?
H11B C18 H12C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 O1 -179.1(2) 2 . . . ?
Br1 C1 C2 O1 -1.1(4) . . . . ?
C3 C1 C2 C3 1.8(4) 2 . . . ?
Br1 C1 C2 C3 179.80(17) . . . . ?
O1 C2 C3 O2 -1.3(4) . . . . ?
C1 C2 C3 O2 177.9(2) . . . . ?
O1 C2 C3 C1 179.1(2) . . . 2 ?
C1 C2 C3 C1 -1.8(4) . . . 2 ?
C6 C4 C5 O3 -178.9(3) 2_767 . . . ?
Br2 C4 C5 O3 0.0(4) . . . . ?
C6 C4 C5 C6 0.6(4) 2_767 . . . ?
Br2 C4 C5 C6 179.43(17) . . . . ?
O3 C5 C6 O4 -1.3(4) . . . . ?
C4 C5 C6 O4 179.2(2) . . . . ?
O3 C5 C6 C4 178.9(2) . . . 2_767 ?
C4 C5 C6 C4 -0.6(4) . . . 2_767 ?
C11 N1 C7 C8 1.9(4) . . . . ?
N1 C7 C8 C9 1.0(4) . . . . ?
N1 C7 C8 C17 -178.5(3) . . . . ?
C7 C8 C9 C10 -2.8(4) . . . . ?
C17 C8 C9 C10 176.7(3) . . . . ?
C8 C9 C10 C11 1.8(4) . . . . ?
C7 N1 C11 C10 -3.0(4) . . . . ?
C7 N1 C11 C16 175.3(2) . . . . ?
C9 C10 C11 N1 1.1(4) . . . . ?
C9 C10 C11 C16 -177.1(3) . . . . ?
C16 N2 C12 C13 0.9(4) . . . . ?
N2 C12 C13 C14 -1.2(4) . . . . ?
N2 C12 C13 C18 178.6(3) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C18 C13 C14 C15 -179.2(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C12 N2 C16 C15 0.1(4) . . . . ?
C12 N2 C16 C11 177.6(2) . . . . ?
C14 C15 C16 N2 -0.7(4) . . . . ?
C14 C15 C16 C11 -178.0(3) . . . . ?
N1 C11 C16 N2 167.44(19) . . . . ?
C10 C11 C16 N2 -14.3(4) . . . . ?
N1 C11 C16 C15 -15.1(4) . . . . ?
C10 C11 C16 C15 163.1(2) . . . . ?

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
O1 H13 O2 . . . 2.673(3) 1.16(5) 2.08(7) 107(4) no
O1 H13 N1 . . . 2.713(3) 1.16(5) 1.65(6) 149(6) no
O4 H14 O3 . . . 2.671(3) 1.14(6) 2.21(5) 101(3) no
N2 H14 O3 . . . 3.046(3) 1.54(6) 2.21(5) 107(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
# start Validation Reply Form
_vrf_PLAT355_H55dmbp-Hba_RT      
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H13      .       1.17 Ang.  
RESPONSE: Essential observation of proton migration in the H-bonds.
;
_vrf_PLAT110_H55dmbp-Hba_RT      
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT112_H55dmbp-Hba_RT      
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT113_H55dmbp-Hba_RT      
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: Essential observation near below the phase transition point.
;
_vrf_PLAT776_H55dmbp-Hba_RT      
;
PROBLEM: Suspect D-H Dist in CIF: N2       --H14       ..       1.54 Ang.  
RESPONSE: Essential observation of proton migration in the H-bonds.
;
# end Validation Reply Form

#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H22bpy-Hia
_database_code_depnum_ccdc_archive 'CCDC 1944396'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H10 I2 N2 O4'
_chemical_formula_moiety         'C16 H10 I2 N2 O4'
_chemical_formula_weight         548.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.4976(15)
_cell_length_b                   9.6911(17)
_cell_length_c                   11.242(2)
_cell_angle_alpha                102.877(3)
_cell_angle_beta                 100.665(2)
_cell_angle_gamma                107.8887(17)
_cell_volume                     826.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3094
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    2.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516.00
_exptl_absorpt_coefficient_mu    3.831
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            12892
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3754
_reflns_number_gt                3418
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0678
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3754
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0392P)²+0.0321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.97
_refine_diff_density_min         -1.11
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0441(12)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
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)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.26018(2) -0.28265(2) 0.10451(2) 0.04461(11) Uani 1 1 d . . . . .
I2 I 1.28509(2) 0.79372(2) 0.92241(2) 0.04514(10) Uani 1 1 d . . . . .
O1 O 0.0674(3) 0.0243(2) 0.25283(16) 0.0444(4) Uani 1 1 d . . . . .
O2 O 0.2553(3) 0.2366(2) 0.16929(18) 0.0557(6) Uani 1 1 d . . . . .
O3 O 0.9497(3) 0.4998(2) 0.75857(16) 0.0487(5) Uani 1 1 d . . . . .
O4 O 0.7354(2) 0.2723(2) 0.81401(16) 0.0459(5) Uani 1 1 d . . . . .
N1 N 0.2839(2) 0.2569(2) 0.44431(18) 0.0361(5) Uani 1 1 d . . . . .
N2 N 0.6835(3) 0.2161(2) 0.56725(19) 0.0390(5) Uani 1 1 d . . . . .
C1 C -0.1023(3) -0.1158(3) 0.0455(2) 0.0313(5) Uani 1 1 d . . . . .
C2 C 0.0289(3) 0.0050(3) 0.1309(2) 0.0332(5) Uani 1 1 d . . . . .
C3 C 0.1403(3) 0.1311(3) 0.0879(2) 0.0344(5) Uani 1 1 d . . . . .
C4 C 1.1173(3) 0.6225(3) 0.9703(2) 0.0312(5) Uani 1 1 d . . . . .
C5 C 0.9786(3) 0.5053(3) 0.8714(2) 0.0323(5) Uani 1 1 d . . . . .
C6 C 0.8587(3) 0.3771(3) 0.9062(2) 0.0326(5) Uani 1 1 d . . . . .
C7 C 0.1853(4) 0.3362(3) 0.4769(3) 0.0468(6) Uani 1 1 d . . . . .
H1 H 0.077857 0.311740 0.421850 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2373(3) 0.4517(3) 0.5882(2) 0.0471(8) Uani 1 1 d . . . . .
H2 H 0.164805 0.501785 0.610437 0.056 Uiso 1 1 calc R U . . .
C9 C 0.4005(4) 0.4916(3) 0.6664(3) 0.0443(6) Uani 1 1 d . . . . .
H3 H 0.439881 0.570674 0.741771 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5048(3) 0.4138(3) 0.6323(2) 0.0371(5) Uani 1 1 d . . . . .
H4 H 0.615468 0.440901 0.683481 0.045 Uiso 1 1 calc R U . . .
C11 C 0.4421(3) 0.2948(3) 0.5206(2) 0.0315(5) Uani 1 1 d . . . . .
C12 C 0.7851(4) 0.1398(3) 0.5345(3) 0.0474(6) Uani 1 1 d . . . . .
H5 H 0.880008 0.148840 0.596410 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7543(4) 0.0495(3) 0.4139(3) 0.0463(7) Uani 1 1 d . . . . .
H6 H 0.827530 -0.000739 0.393665 0.056 Uiso 1 1 calc R U . . .
C14 C 0.6122(4) 0.0352(3) 0.3232(3) 0.0448(6) Uani 1 1 d . . . . .
H7 H 0.586112 -0.027623 0.240934 0.054 Uiso 1 1 calc R U . . .
C15 C 0.5088(3) 0.1145(3) 0.3551(2) 0.0421(6) Uani 1 1 d . . . . .
H8 H 0.413939 0.107252 0.294053 0.051 Uiso 1 1 calc R U . . .
C16 C 0.5468(3) 0.2048(3) 0.4782(2) 0.0309(5) Uani 1 1 d . . . . .
H9 H 0.179(4) 0.136(4) 0.288(3) 0.079(11) Uiso 1 1 d . . . . .
H10 H 0.758(4) 0.308(4) 0.718(4) 0.086(12) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.081(2) . ?
I2 C4 2.075(2) . ?
O1 C2 1.305(3) . ?
O1 H9 1.13(3) . ?
O2 C3 1.215(3) . ?
O3 C5 1.232(3) . ?
O4 C6 1.296(3) . ?
O4 H10 1.24(4) . ?
N1 C11 1.344(3) . ?
N1 C7 1.346(3) . ?
N2 C16 1.344(3) . ?
N2 C12 1.348(3) . ?
C1 C2 1.355(3) . ?
C1 C3 1.437(3) 2 ?
C2 C3 1.532(4) . ?
C4 C6 1.364(3) 2_767 ?
C4 C5 1.430(3) . ?
C5 C6 1.524(4) . ?
C7 C8 1.371(4) . ?
C7 H1 0.9300 . ?
C8 C9 1.383(4) . ?
C8 H2 0.9300 . ?
C9 C10 1.382(4) . ?
C9 H3 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H4 0.9300 . ?
C11 C16 1.492(4) . ?
C12 C13 1.368(4) . ?
C12 H5 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H6 0.9300 . ?
C14 C15 1.379(4) . ?
C14 H7 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H8 0.9300 . ?

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
_geom_angle_publ_flag
C2 O1 H9 100.9(17) . . ?
C6 O4 H10 104.5(17) . . ?
C11 N1 C7 119.4(2) . . ?
C16 N2 C12 119.1(2) . . ?
C2 C1 C3 121.5(2) . 2 ?
C2 C1 I1 120.70(18) . . ?
C3 C1 I1 117.79(17) 2 . ?
O1 C2 C1 123.7(2) . . ?
O1 C2 C3 115.7(2) . . ?
C1 C2 C3 120.6(2) . . ?
O2 C3 C1 124.8(2) . 2 ?
O2 C3 C2 117.4(2) . . ?
C1 C3 C2 117.9(2) 2 . ?
C6 C4 C5 121.5(2) 2_767 . ?
C6 C4 I2 120.00(18) 2_767 . ?
C5 C4 I2 118.51(16) . . ?
O3 C5 C4 124.4(2) . . ?
O3 C5 C6 117.2(2) . . ?
C4 C5 C6 118.42(19) . . ?
O4 C6 C4 123.2(2) . 2_767 ?
O4 C6 C5 116.7(2) . . ?
C4 C6 C5 120.1(2) 2_767 . ?
N1 C7 C8 122.4(3) . . ?
N1 C7 H1 118.8 . . ?
C8 C7 H1 118.8 . . ?
C7 C8 C9 118.2(3) . . ?
C7 C8 H2 120.9 . . ?
C9 C8 H2 120.9 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H3 120.1 . . ?
C8 C9 H3 120.1 . . ?
C9 C10 C11 119.0(2) . . ?
C9 C10 H4 120.5 . . ?
C11 C10 H4 120.5 . . ?
N1 C11 C10 121.1(2) . . ?
N1 C11 C16 116.9(2) . . ?
C10 C11 C16 122.0(2) . . ?
N2 C12 C13 122.7(3) . . ?
N2 C12 H5 118.6 . . ?
C13 C12 H5 118.6 . . ?
C12 C13 C14 118.2(3) . . ?
C12 C13 H6 120.9 . . ?
C14 C13 H6 120.9 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H7 120.2 . . ?
C15 C14 H7 120.2 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H8 120.2 . . ?
C16 C15 H8 120.2 . . ?
N2 C16 C15 120.7(2) . . ?
N2 C16 C11 116.2(2) . . ?
C15 C16 C11 123.1(2) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 O1 179.5(2) 2 . . . ?
I1 C1 C2 O1 1.3(3) . . . . ?
C3 C1 C2 C3 0.7(4) 2 . . . ?
I1 C1 C2 C3 -177.43(16) . . . . ?
O1 C2 C3 O2 0.8(3) . . . . ?
C1 C2 C3 O2 179.7(3) . . . . ?
O1 C2 C3 C1 -179.6(2) . . . 2 ?
C1 C2 C3 C1 -0.7(4) . . . 2 ?
C6 C4 C5 O3 179.3(2) 2_767 . . . ?
I2 C4 C5 O3 -1.1(3) . . . . ?
C6 C4 C5 C6 -1.4(4) 2_767 . . . ?
I2 C4 C5 C6 178.19(15) . . . . ?
O3 C5 C6 O4 -0.1(3) . . . . ?
C4 C5 C6 O4 -179.4(2) . . . . ?
O3 C5 C6 C4 -179.3(2) . . . 2_767 ?
C4 C5 C6 C4 1.4(4) . . . 2_767 ?
C11 N1 C7 C8 -2.5(4) . . . . ?
N1 C7 C8 C9 3.0(4) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C7 N1 C11 C10 0.2(3) . . . . ?
C7 N1 C11 C16 -178.8(2) . . . . ?
C9 C10 C11 N1 1.6(4) . . . . ?
C9 C10 C11 C16 -179.5(2) . . . . ?
C16 N2 C12 C13 -0.6(4) . . . . ?
N2 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 1.8(4) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C12 N2 C16 C15 1.1(4) . . . . ?
C12 N2 C16 C11 -178.8(2) . . . . ?
C14 C15 C16 N2 -0.1(4) . . . . ?
C14 C15 C16 C11 179.8(3) . . . . ?
N1 C11 C16 N2 -163.58(17) . . . . ?
C10 C11 C16 N2 17.4(4) . . . . ?
N1 C11 C16 C15 16.6(4) . . . . ?
C10 C11 C16 C15 -162.4(2) . . . . ?

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
O1 H9 O2 . . . 2.657(3) 1.13(3) 1.91(4) 120(2) no
O1 H9 N1 . . . 2.631(2) 1.13(3) 1.77(3) 130(3) no
O4 H10 O3 . . . 2.671(3) 1.24(4) 1.95(3) 112.0(19) no
O4 H10 N2 . . . 2.629(3) 1.24(4) 1.63(4) 133(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
# start Validation Reply Form
_vrf_PLAT355_H22bpy-Hia          
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H9       .       1.13 Ang.  
RESPONSE: Essential observation of proton migration in the H-bonds.
;
_vrf_PLAT110_H22bpy-Hia          
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Essential observation near below the phase transition point..
;
_vrf_PLAT112_H22bpy-Hia          
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: Essential observation near below the phase transition point..
;
_vrf_PLAT113_H22bpy-Hia          
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: Essential observation near below the phase transition point..
;
# end Validation Reply Form

#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H55dmbp-Hba_360K
_database_code_depnum_ccdc_archive 'CCDC 1944403'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H14 Br2 N2 O4'
_chemical_formula_moiety         'C18 H14 Br2 N2 O4'
_chemical_formula_weight         482.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.8779(2)
_cell_length_b                   8.1042(3)
_cell_length_c                   11.8636(7)
_cell_angle_alpha                108.4731(13)
_cell_angle_beta                 91.2897(17)
_cell_angle_gamma                98.2241(15)
_cell_volume                     439.09(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2749
_cell_measurement_theta_min      6.66
_cell_measurement_theta_max      67.72
_cell_measurement_temperature    360
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            dark_red
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             238.00
_exptl_absorpt_coefficient_mu    1.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      360
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.00000
_diffrn_measurement_device_type  'IPDSC (Rigaku)'
_diffrn_reflns_number            1773
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_theta_max         44.951
_diffrn_reflns_theta_min         7.163
_diffrn_reflns_theta_full        36.870
_diffrn_measured_fraction_theta_max 0.468
_diffrn_measured_fraction_theta_full 0.541
_diffrn_reflns_Laue_measured_fraction_max 0.468
_diffrn_reflns_Laue_measured_fraction_full 0.541
_diffrn_reflns_point_group_measured_fraction_max 0.468
_diffrn_reflns_point_group_measured_fraction_full 0.541
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1210
_reflns_number_gt                1141
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0940
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1210
_refine_ls_number_parameters     120
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0476P)²+0.2932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.083(5)

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)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

# start Validation Reply Form
_vrf_PLAT029_H55dmbp-Hba_360K    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.541 Why?  
RESPONSE:
The data have been collected on 1-circle goniometer with IP area detector 
diffractometer. It is only the very high angle data that is incomplete due to 
the shape of the area detector, and we have ca. 100% coverage in the low angle 
data. This will always be a problem with area detector data that is not 
truncated. In addition, changing the direction of crystal is difficult 
due to the N2 blower for the temperaature control. The obtained 
analysis was sufficient to elucidate the molecular structure. 
;
_vrf_PLAT430_H55dmbp-Hba_360K    
;
PROBLEM: Short Inter D...A Contact  O2       ..N1       .       2.71 Ang.  
RESPONSE: 
The two molecules are connected strong hydrogen bond.  This is 
essential quality for this compound.  
;
_vrf_PLAT910_H55dmbp-Hba_360K    
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE:
A part of the data are missing by the blind area due to the heating device. 
;
_vrf_PLAT911_H55dmbp-Hba_360K    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        610 Report
RESPONSE:
A part of the data are missing by the blind area due to the heating device. 
;
# end Validation Reply Form



