# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_BrPQ-1
_database_code_depnum_ccdc_archive 'CCDC 2088687'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2021-07-28 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C62 H36.28 Br1.72 Cl8 N4 O8'
_chemical_formula_moiety         'C38 H20.28 Br1.72 N4 O8, 4(C6 H4 Cl2)'
_chemical_formula_weight         1386.33
_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_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.48306(15)
_cell_length_b                   15.3486(4)
_cell_length_c                   17.9094(5)
_cell_angle_alpha                79.089(2)
_cell_angle_beta                 84.670(2)
_cell_angle_gamma                88.069(2)
_cell_volume                     1473.36(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    10350
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      31.55
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.48
_exptl_absorpt_coefficient_mu    1.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_T_max  0.851

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

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  PILATUS200K
_diffrn_reflns_number            23839
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_theta_max         31.454
_diffrn_reflns_theta_min         3.220
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8344
_reflns_number_gt                7547
_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).,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0919
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         8344
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0556P)²+0.3580P] 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         0.45
_refine_diff_density_min         -0.51
_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
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 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)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 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)
;
Cl Cl 0.1484 0.1585
;
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 0.61778(3) 0.49760(2) 0.65335(2) 0.02492(6) Uani 0.86 1 d . . P A 1
O1 O -0.23414(19) 0.99752(7) 0.43846(7) 0.0330(2) Uani 1 1 d . . . . .
H1O H -0.361175 1.025836 0.450246 0.040 Uiso 0.5 1 calc R U P . .
O2 O -0.37316(19) 0.90164(7) 0.54365(6) 0.0333(2) Uani 1 1 d . . . . .
H2O H -0.472576 0.943667 0.547797 0.040 Uiso 0.5 1 calc R U P . .
O3 O 1.2404(2) 0.02968(9) 0.94364(7) 0.0508(4) Uani 1 1 d . . . . .
H3O H 1.284084 -0.002595 0.983653 0.061 Uiso 1 1 calc R U . . .
O4 O 1.6190(2) 0.08262(9) 0.93795(7) 0.0491(4) Uani 1 1 d . . . . .
N1 N 0.61477(18) 0.62180(6) 0.50159(6) 0.01695(18) Uani 1 1 d . . . . .
N2 N 1.06360(18) 0.37333(6) 0.63117(5) 0.01761(18) Uani 1 1 d . . . . .
C1 C 0.5856(2) 0.68179(7) 0.43970(6) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.8028(2) 0.56100(7) 0.50007(6) 0.0156(2) Uani 1 1 d . . . . .
C3 C 0.8341(2) 0.49686(7) 0.56598(6) 0.0166(2) Uani 1 1 d . . . . .
H3 H 0.722551 0.494943 0.610118 0.020 Uiso 0.14 1 calc R U P A 2
C4 C 1.0306(2) 0.43561(7) 0.56651(6) 0.0156(2) Uani 1 1 d . . . . .
C5 C 1.2519(2) 0.31817(7) 0.62954(6) 0.0174(2) Uani 1 1 d . . . . .
C6 C 0.3818(2) 0.74719(7) 0.44853(7) 0.0180(2) Uani 1 1 d . . . . .
C7 C 0.3715(2) 0.83249(8) 0.40334(7) 0.0215(2) Uani 1 1 d . . . . .
H7 H 0.497866 0.850942 0.364049 0.026 Uiso 1 1 calc R U . . .
C8 C 0.1761(2) 0.89028(8) 0.41596(8) 0.0235(2) Uani 1 1 d . . . . .
H8 H 0.169802 0.947763 0.385062 0.028 Uiso 1 1 calc R U . . .
C9 C -0.0094(2) 0.86401(8) 0.47361(8) 0.0226(2) Uani 1 1 d . . . . .
C10 C 0.0019(2) 0.78003(8) 0.52015(8) 0.0224(2) Uani 1 1 d . . . . .
H10 H -0.122789 0.762421 0.560181 0.027 Uiso 1 1 calc R U . . .
C11 C 0.1961(2) 0.72241(8) 0.50763(7) 0.0202(2) Uani 1 1 d . . . . .
H11 H 0.203343 0.665513 0.539456 0.024 Uiso 1 1 calc R U . . .
C12 C -0.2199(2) 0.92489(8) 0.48649(8) 0.0243(2) Uani 1 1 d . . . . .
C13 C 1.2911(2) 0.25772(8) 0.70355(7) 0.0199(2) Uani 1 1 d . . . . .
C14 C 1.4993(2) 0.26617(8) 0.74048(7) 0.0241(2) Uani 1 1 d . . . . .
H14 H 1.616588 0.310068 0.718748 0.029 Uiso 1 1 calc R U . . .
C15 C 1.5343(2) 0.20990(9) 0.80938(8) 0.0274(3) Uani 1 1 d . . . . .
H15 H 1.675345 0.215826 0.834960 0.033 Uiso 1 1 calc R U . . .
C16 C 1.3642(2) 0.14504(10) 0.84106(8) 0.0286(3) Uani 1 1 d . . . . .
C17 C 1.1536(2) 0.13737(10) 0.80487(8) 0.0315(3) Uani 1 1 d . . . . .
H17 H 1.035679 0.093792 0.826897 0.038 Uiso 1 1 calc R U . . .
C18 C 1.1175(2) 0.19410(9) 0.73619(8) 0.0268(3) Uani 1 1 d . . . . .
H18 H 0.973818 0.189448 0.711446 0.032 Uiso 1 1 calc R U . . .
C19 C 1.4178(3) 0.08277(11) 0.91246(9) 0.0352(3) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_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 C3 1.8753(11) . ?
O1 C12 1.2777(16) . ?
O1 H1O 0.8400 . ?
O2 C12 1.2661(18) . ?
O2 H2O 0.8400 . ?
O3 C19 1.3048(18) . ?
O3 H3O 0.8400 . ?
O4 C19 1.2318(18) . ?
N1 C1 1.3184(13) . ?
N1 C2 1.3689(13) . ?
N2 C5 1.3150(14) . ?
N2 C4 1.3769(13) . ?
C1 C5 1.4578(16) 2_766 ?
C1 C6 1.4943(15) . ?
C2 C3 1.4067(14) . ?
C2 C4 1.4270(15) 2_766 ?
C3 C4 1.4051(14) . ?
C3 H3 0.9500 . ?
C5 C13 1.4957(15) . ?
C6 C7 1.4053(15) . ?
C6 C11 1.4055(17) . ?
C7 C8 1.3975(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3921(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3991(17) . ?
C9 C12 1.4894(16) . ?
C10 C11 1.3906(15) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.3930(17) . ?
C13 C18 1.3945(18) . ?
C14 C15 1.3911(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3905(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3946(19) . ?
C16 C19 1.4912(17) . ?
C17 C18 1.3923(16) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C12 O1 H1O 109.5 . . ?
C12 O2 H2O 109.5 . . ?
C19 O3 H3O 109.5 . . ?
C1 N1 C2 118.87(10) . . ?
C5 N2 C4 118.16(10) . . ?
N1 C1 C5 120.34(10) . 2_766 ?
N1 C1 C6 114.50(10) . . ?
C5 C1 C6 125.15(9) 2_766 . ?
N1 C2 C3 119.00(10) . . ?
N1 C2 C4 120.54(9) . 2_766 ?
C3 C2 C4 120.43(9) . 2_766 ?
C4 C3 C2 119.96(10) . . ?
C4 C3 Br1 121.04(8) . . ?
C2 C3 Br1 118.96(8) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N2 C4 C3 120.17(10) . . ?
N2 C4 C2 120.22(9) . 2_766 ?
C3 C4 C2 119.61(9) . 2_766 ?
N2 C5 C1 121.69(10) . 2_766 ?
N2 C5 C13 115.58(10) . . ?
C1 C5 C13 122.71(10) 2_766 . ?
C7 C6 C11 118.73(10) . . ?
C7 C6 C1 123.76(11) . . ?
C11 C6 C1 117.45(10) . . ?
C8 C7 C6 120.26(12) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.31(11) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.95(11) . . ?
C8 C9 C12 120.48(11) . . ?
C10 C9 C12 119.57(12) . . ?
C11 C10 C9 119.81(12) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C6 120.90(11) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
O2 C12 O1 124.22(12) . . ?
O2 C12 C9 118.43(12) . . ?
O1 C12 C9 117.35(12) . . ?
C14 C13 C18 120.05(11) . . ?
C14 C13 C5 119.83(11) . . ?
C18 C13 C5 120.11(11) . . ?
C15 C14 C13 119.56(12) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.42(12) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.15(11) . . ?
C15 C16 C19 118.32(12) . . ?
C17 C16 C19 121.49(12) . . ?
C18 C17 C16 119.44(12) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C13 120.35(12) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
O4 C19 O3 124.09(12) . . ?
O4 C19 C16 120.61(13) . . ?
O3 C19 C16 115.30(12) . . ?

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 1.35(17) . . . 2_766 ?
C2 N1 C1 C6 -177.55(10) . . . . ?
C1 N1 C2 C3 -179.93(11) . . . . ?
C1 N1 C2 C4 2.12(17) . . . 2_766 ?
N1 C2 C3 C4 -177.94(11) . . . . ?
C4 C2 C3 C4 0.01(19) 2_766 . . . ?
N1 C2 C3 Br1 -0.25(15) . . . . ?
C4 C2 C3 Br1 177.70(9) 2_766 . . . ?
C5 N2 C4 C3 -178.99(11) . . . . ?
C5 N2 C4 C2 0.30(17) . . . 2_766 ?
C2 C3 C4 N2 179.28(11) . . . . ?
Br1 C3 C4 N2 1.63(16) . . . . ?
C2 C3 C4 C2 -0.01(19) . . . 2_766 ?
Br1 C3 C4 C2 -177.66(9) . . . 2_766 ?
C4 N2 C5 C1 -3.83(17) . . . 2_766 ?
C4 N2 C5 C13 174.61(10) . . . . ?
N1 C1 C6 C7 155.74(12) . . . . ?
C5 C1 C6 C7 -23.10(19) 2_766 . . . ?
N1 C1 C6 C11 -21.62(16) . . . . ?
C5 C1 C6 C11 159.54(11) 2_766 . . . ?
C11 C6 C7 C8 -1.72(18) . . . . ?
C1 C6 C7 C8 -179.05(11) . . . . ?
C6 C7 C8 C9 0.28(19) . . . . ?
C7 C8 C9 C10 1.23(19) . . . . ?
C7 C8 C9 C12 -179.07(12) . . . . ?
C8 C9 C10 C11 -1.27(19) . . . . ?
C12 C9 C10 C11 179.02(12) . . . . ?
C9 C10 C11 C6 -0.20(19) . . . . ?
C7 C6 C11 C10 1.68(18) . . . . ?
C1 C6 C11 C10 179.18(11) . . . . ?
C8 C9 C12 O2 -173.82(12) . . . . ?
C10 C9 C12 O2 5.89(18) . . . . ?
C8 C9 C12 O1 6.45(18) . . . . ?
C10 C9 C12 O1 -173.84(12) . . . . ?
N2 C5 C13 C14 -113.96(13) . . . . ?
C1 C5 C13 C14 64.46(17) 2_766 . . . ?
N2 C5 C13 C18 64.90(16) . . . . ?
C1 C5 C13 C18 -116.68(14) 2_766 . . . ?
C18 C13 C14 C15 1.0(2) . . . . ?
C5 C13 C14 C15 179.84(12) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C17 -1.6(2) . . . . ?
C14 C15 C16 C19 176.24(15) . . . . ?
C15 C16 C17 C18 1.1(2) . . . . ?
C19 C16 C17 C18 -176.67(15) . . . . ?
C16 C17 C18 C13 0.4(2) . . . . ?
C14 C13 C18 C17 -1.5(2) . . . . ?
C5 C13 C18 C17 179.67(13) . . . . ?
C15 C16 C19 O4 -7.8(3) . . . . ?
C17 C16 C19 O4 170.05(18) . . . . ?
C15 C16 C19 O3 173.11(16) . . . . ?
C17 C16 C19 O3 -9.0(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 H1O O2 . . 2_476 2.6400(15) 0.840 1.811 168.7 no
O2 H2O O1 . . 2_476 2.6400(15) 0.840 1.837 159.4 no
O3 H3O O4 . . 2_857 2.6255(17) 0.840 1.790 172.7 no

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





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"4,4',4'',4'''-(5,10-dibromopyrazino[2,3-g]quinoxaline-2,3,7,8-tetrayl)tetrabenzoic acid"
_chemical_name_common            BrPQ-1
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF, o-dichlorobenzene'
####################################################################### 
# 
# 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_BrPQ-3a
_database_code_depnum_ccdc_archive 'CCDC 2088690'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2021-07-28 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C38 H20.28 Br1.72 N4 O8'
_chemical_formula_moiety         'C38 H20.28 Br1.72 N4 O8'
_chemical_formula_weight         798.32
_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_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.584(2)
_cell_length_b                   12.305(3)
_cell_length_c                   15.827(5)
_cell_angle_alpha                103.84(2)
_cell_angle_beta                 93.62(3)
_cell_angle_gamma                91.13(3)
_cell_volume                     1053.1(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    628
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      29.76
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       orange
_exptl_crystal_colour            prism
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400.48
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.396
_exptl_absorpt_correction_T_max  0.918

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

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  PILATUS200K
_diffrn_reflns_number            17280
_diffrn_reflns_av_unetI/netI     0.2642
_diffrn_reflns_av_R_equivalents  0.2401
_diffrn_reflns_theta_max         31.468
_diffrn_reflns_theta_min         3.413
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6035
_reflns_number_gt                2063
_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).,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2465
_refine_ls_R_factor_gt           0.1058
_refine_ls_wR_factor_ref         0.3275
_refine_ls_wR_factor_gt          0.2453
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6035
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1581P)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         1.38
_refine_diff_density_min         -0.61
_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 0.0033 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)
;
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)
;
Br Br -0.2901 2.4595
;
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 0.34170(19) 0.27902(9) 0.48534(7) 0.0604(4) Uani 0.86 1 d . . P A 1
O1 O 1.2764(9) 0.5880(4) 0.9967(3) 0.0465(14) Uani 1 1 d . . . . .
O2 O 1.3483(10) 0.4324(4) 0.8946(3) 0.0545(16) Uani 1 1 d . . . . .
H2O H 1.485961 0.440662 0.917006 0.065 Uiso 1 1 calc R U . . .
O3 O -0.3810(12) -0.1754(5) 0.0181(5) 0.080(2) Uani 1 1 d . . . . .
O4 O -0.7347(12) -0.1764(6) 0.0793(5) 0.095(3) Uani 1 1 d . . . . .
H4O H -0.747012 -0.241153 0.050009 0.113 Uiso 1 1 calc R U . . .
N1 N 0.3896(10) 0.5009(5) 0.6195(4) 0.0440(16) Uani 1 1 d . . . . .
N2 N -0.1085(10) 0.3058(5) 0.3647(4) 0.0406(15) Uani 1 1 d . . . . .
C1 C 0.4378(13) 0.5911(6) 0.6840(5) 0.0422(19) Uani 1 1 d . . . . .
C2 C 0.1963(13) 0.5007(7) 0.5607(5) 0.0434(19) Uani 1 1 d . . . . .
C3 C 0.1483(12) 0.4045(6) 0.4919(5) 0.0406(19) Uani 1 1 d . . . . .
H3 H 0.245567 0.343025 0.486337 0.049 Uiso 0.14 1 calc R U P A 2
C4 C -0.0517(12) 0.4032(6) 0.4311(5) 0.0394(18) Uani 1 1 d . . . . .
C5 C -0.2979(12) 0.3056(6) 0.3097(4) 0.0376(17) Uani 1 1 d . . . . .
C6 C 0.6431(13) 0.5795(6) 0.7479(5) 0.0404(18) Uani 1 1 d . . . . .
C7 C 0.6666(13) 0.6420(7) 0.8359(5) 0.048(2) Uani 1 1 d . . . . .
H7 H 0.553970 0.695028 0.856103 0.058 Uiso 1 1 calc R U . . .
C8 C 0.8600(13) 0.6250(6) 0.8937(5) 0.0414(19) Uani 1 1 d . . . . .
H8 H 0.878494 0.668330 0.950663 0.050 Uiso 1 1 calc R U . . .
C9 C 1.0229(13) 0.5410(6) 0.8628(5) 0.0393(18) Uani 1 1 d . . . . .
C10 C 1.0000(14) 0.4760(7) 0.7767(5) 0.0443(19) Uani 1 1 d . . . . .
H10 H 1.109323 0.421045 0.757371 0.053 Uiso 1 1 calc R U . . .
C11 C 0.8100(13) 0.4948(6) 0.7197(5) 0.044(2) Uani 1 1 d . . . . .
H11 H 0.793358 0.451127 0.662796 0.053 Uiso 1 1 calc R U . . .
C12 C 1.2290(13) 0.5226(6) 0.9248(5) 0.0424(19) Uani 1 1 d . . . . .
C13 C -0.3626(13) 0.1965(6) 0.2457(5) 0.0412(19) Uani 1 1 d . . . . .
C14 C -0.1985(14) 0.1490(7) 0.1841(5) 0.048(2) Uani 1 1 d . . . . .
H14 H -0.053209 0.186151 0.181901 0.058 Uiso 1 1 calc R U . . .
C15 C -0.2579(15) 0.0435(7) 0.1253(6) 0.055(2) Uani 1 1 d . . . . .
H15 H -0.153729 0.012675 0.083134 0.066 Uiso 1 1 calc R U . . .
C16 C -0.4704(14) -0.0132(7) 0.1309(6) 0.053(2) Uani 1 1 d . . . . .
C17 C -0.6333(15) 0.0318(7) 0.1921(6) 0.064(3) Uani 1 1 d . . . . .
H17 H -0.775331 -0.007113 0.195556 0.076 Uiso 1 1 calc R U . . .
C18 C -0.5777(14) 0.1375(7) 0.2482(6) 0.054(2) Uani 1 1 d . . . . .
H18 H -0.686906 0.169085 0.288280 0.065 Uiso 1 1 calc R U . . .
C19 C -0.5230(18) -0.1307(8) 0.0683(7) 0.071(3) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_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 C3 1.888(7) . ?
O1 C12 1.236(9) . ?
O2 C12 1.312(8) . ?
O2 H2O 0.8200 . ?
O3 C19 1.204(11) . ?
O4 C19 1.338(13) . ?
O4 H4O 0.8200 . ?
N1 C1 1.325(9) . ?
N1 C2 1.380(8) . ?
N2 C5 1.327(8) . ?
N2 C4 1.408(9) . ?
C1 C5 1.491(10) 2_566 ?
C1 C6 1.512(10) . ?
C2 C3 1.412(10) . ?
C2 C4 1.430(10) 2_566 ?
C3 C4 1.425(9) . ?
C3 H3 0.9300 . ?
C5 C13 1.498(10) . ?
C6 C7 1.417(10) . ?
C6 C11 1.423(10) . ?
C7 C8 1.422(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.408(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(10) . ?
C9 C12 1.521(9) . ?
C10 C11 1.407(10) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 C18 1.399(11) . ?
C13 C14 1.412(11) . ?
C14 C15 1.423(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.395(12) . ?
C16 C19 1.555(11) . ?
C17 C18 1.405(11) . ?
C17 H17 0.9300 . ?
C18 H18 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
C12 O2 H2O 109.5 . . ?
C19 O4 H4O 109.5 . . ?
C1 N1 C2 119.0(6) . . ?
C5 N2 C4 118.4(6) . . ?
N1 C1 C5 121.2(6) . 2_566 ?
N1 C1 C6 114.6(6) . . ?
C5 C1 C6 124.2(6) 2_566 . ?
N1 C2 C3 118.4(6) . . ?
N1 C2 C4 120.4(6) . 2_566 ?
C3 C2 C4 121.2(6) . 2_566 ?
C2 C3 C4 118.8(6) . . ?
C2 C3 Br1 119.4(5) . . ?
C4 C3 Br1 121.7(5) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N2 C4 C3 119.4(6) . . ?
N2 C4 C2 120.7(6) . 2_566 ?
C3 C4 C2 120.0(6) . 2_566 ?
N2 C5 C1 120.1(6) . 2_566 ?
N2 C5 C13 116.0(6) . . ?
C1 C5 C13 123.9(6) 2_566 . ?
C7 C6 C11 118.5(6) . . ?
C7 C6 C1 123.6(6) . . ?
C11 C6 C1 117.7(6) . . ?
C6 C7 C8 121.0(6) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 118.7(6) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 121.5(6) . . ?
C10 C9 C12 119.9(6) . . ?
C8 C9 C12 118.6(6) . . ?
C9 C10 C11 119.4(6) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C6 121.0(7) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
O1 C12 O2 124.2(6) . . ?
O1 C12 C9 122.0(6) . . ?
O2 C12 C9 113.8(6) . . ?
C18 C13 C14 118.9(7) . . ?
C18 C13 C5 121.4(7) . . ?
C14 C13 C5 119.6(7) . . ?
C13 C14 C15 119.2(8) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.1(8) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.4(7) . . ?
C15 C16 C19 118.5(8) . . ?
C17 C16 C19 120.1(9) . . ?
C16 C17 C18 118.4(8) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C13 C18 C17 121.9(8) . . ?
C13 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
O3 C19 O4 125.0(8) . . ?
O3 C19 C16 122.2(9) . . ?
O4 C19 C16 112.8(8) . . ?

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 -4.3(12) . . . 2_566 ?
C2 N1 C1 C6 176.2(7) . . . . ?
C1 N1 C2 C3 179.4(8) . . . . ?
C1 N1 C2 C4 0.5(12) . . . 2_566 ?
N1 C2 C3 C4 179.6(7) . . . . ?
C4 C2 C3 C4 -1.5(13) 2_566 . . . ?
N1 C2 C3 Br1 2.2(11) . . . . ?
C4 C2 C3 Br1 -178.9(6) 2_566 . . . ?
C5 N2 C4 C3 178.8(7) . . . . ?
C5 N2 C4 C2 0.5(11) . . . 2_566 ?
C2 C3 C4 N2 -176.9(8) . . . . ?
Br1 C3 C4 N2 0.5(11) . . . . ?
C2 C3 C4 C2 1.5(13) . . . 2_566 ?
Br1 C3 C4 C2 178.9(6) . . . 2_566 ?
C4 N2 C5 C1 3.2(11) . . . 2_566 ?
C4 N2 C5 C13 -174.6(7) . . . . ?
N1 C1 C6 C7 -154.2(8) . . . . ?
C5 C1 C6 C7 26.3(13) 2_566 . . . ?
N1 C1 C6 C11 20.5(11) . . . . ?
C5 C1 C6 C11 -159.0(8) 2_566 . . . ?
C11 C6 C7 C8 3.3(12) . . . . ?
C1 C6 C7 C8 178.0(7) . . . . ?
C6 C7 C8 C9 -2.7(12) . . . . ?
C7 C8 C9 C10 1.0(12) . . . . ?
C7 C8 C9 C12 -179.8(7) . . . . ?
C8 C9 C10 C11 -0.1(12) . . . . ?
C12 C9 C10 C11 -179.3(7) . . . . ?
C9 C10 C11 C6 0.8(13) . . . . ?
C7 C6 C11 C10 -2.4(12) . . . . ?
C1 C6 C11 C10 -177.4(8) . . . . ?
C10 C9 C12 O1 169.4(8) . . . . ?
C8 C9 C12 O1 -9.8(12) . . . . ?
C10 C9 C12 O2 -10.6(11) . . . . ?
C8 C9 C12 O2 170.2(7) . . . . ?
N2 C5 C13 C18 114.2(8) . . . . ?
C1 C5 C13 C18 -63.6(11) 2_566 . . . ?
N2 C5 C13 C14 -62.6(10) . . . . ?
C1 C5 C13 C14 119.7(8) 2_566 . . . ?
C18 C13 C14 C15 1.1(11) . . . . ?
C5 C13 C14 C15 178.0(7) . . . . ?
C13 C14 C15 C16 -2.3(12) . . . . ?
C14 C15 C16 C17 1.5(13) . . . . ?
C14 C15 C16 C19 -177.2(7) . . . . ?
C15 C16 C17 C18 0.4(14) . . . . ?
C19 C16 C17 C18 179.1(8) . . . . ?
C14 C13 C18 C17 0.8(13) . . . . ?
C5 C13 C18 C17 -176.0(8) . . . . ?
C16 C17 C18 C13 -1.6(14) . . . . ?
C15 C16 C19 O3 3.2(14) . . . . ?
C17 C16 C19 O3 -175.6(9) . . . . ?
C15 C16 C19 O4 -179.3(8) . . . . ?
C17 C16 C19 O4 1.9(13) . . . . ?

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
O2 H2O O1 . . 2_867 2.681(8) 0.820 1.942 149.5 no
O4 H4O O1 . . 1_344 2.885(8) 0.820 2.080 167.3 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_RINTA01_BrPQ-3a             
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Due to heating the crystal up to 633 K, crystallinity became lower.
;
_vrf_PLAT020_BrPQ-3a             
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.240 Report
RESPONSE: Due to heating the crystal up to 633 K, crystallinity became lower.
;
_vrf_PLAT026_BrPQ-3a             
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        34% Check 
RESPONSE: Due to heating the crystal up to 633 K, 
diffraction peaks became much weaker in the wide angle region.
;
# end Validation Reply Form
#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"4,4',4'',4'''-(5,10-dibromopyrazino[2,3-g]quinoxaline-2,3,7,8-tetrayl)tetrabenzoic acid"
_chemical_name_common            BrPQ-3a
_exptl_crystal_recrystallization_method 
'heat-induced structural change from BrPQ-2a'
####################################################################### 
# 
# 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_BrPQ-2a
_database_code_depnum_ccdc_archive 'CCDC 2088689'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2021-07-28 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C38 H20.28 Br1.72 N4 O8'
_chemical_formula_moiety         'C38 H20.28 Br1.72 N4 O8'
_chemical_formula_weight         798.32
_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_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.4836(4)
_cell_length_b                   11.8374(12)
_cell_length_c                   15.4284(12)
_cell_angle_alpha                102.618(8)
_cell_angle_beta                 92.409(6)
_cell_angle_gamma                92.015(7)
_cell_volume                     975.42(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1475
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      21.09
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400.48
_exptl_absorpt_coefficient_mu    1.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  0.982

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

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  PILATUS200K
_diffrn_reflns_number            13446
_diffrn_reflns_av_unetI/netI     0.1996
_diffrn_reflns_av_R_equivalents  0.1160
_diffrn_reflns_theta_max         28.805
_diffrn_reflns_theta_min         1.765
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4617
_reflns_number_gt                1934
_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).,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1991
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.2222
_refine_ls_wR_factor_gt          0.1760
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4617
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1003P)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         0.58
_refine_diff_density_min         -0.52
_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 0.0033 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)
;
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)
;
Br Br -0.2901 2.4595
;
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 0.32539(15) 0.26981(7) 0.48763(6) 0.0609(4) Uani 0.86 1 d . . P A 1
O1 O 1.2724(7) 0.5850(3) 0.9951(3) 0.0410(11) Uani 1 1 d . . . . .
O2 O 1.3419(7) 0.4240(3) 0.8951(3) 0.0504(13) Uani 1 1 d . . . . .
H2O H 1.448224 0.416105 0.933822 0.060 Uiso 1 1 calc R U . . .
O3 O -0.3868(8) -0.1768(4) 0.0169(3) 0.0634(15) Uani 1 1 d . . . . .
O4 O -0.7432(8) -0.1818(4) 0.0810(3) 0.0661(16) Uani 1 1 d . . . . .
H4O H -0.753141 -0.250723 0.051792 0.079 Uiso 1 1 calc R U . . .
N1 N 0.3860(8) 0.4971(4) 0.6200(3) 0.0400(14) Uani 1 1 d . . . . .
N2 N -0.1142(9) 0.3048(4) 0.3662(3) 0.0424(14) Uani 1 1 d . . . . .
C1 C 0.4389(10) 0.5891(5) 0.6837(4) 0.0381(16) Uani 1 1 d . . . . .
C2 C 0.1985(10) 0.4995(5) 0.5591(4) 0.0385(16) Uani 1 1 d . . . . .
C3 C 0.1419(10) 0.4019(5) 0.4931(4) 0.0413(17) Uani 1 1 d . . . . .
H3 H 0.236397 0.335353 0.489137 0.050 Uiso 0.14 1 calc R U P A 2
C4 C -0.0555(10) 0.4006(5) 0.4315(4) 0.0404(17) Uani 1 1 d . . . . .
C5 C -0.3038(11) 0.3063(5) 0.3114(4) 0.0418(17) Uani 1 1 d . . . . .
C6 C 0.6400(10) 0.5749(5) 0.7475(4) 0.0425(17) Uani 1 1 d . . . . .
C7 C 0.6680(10) 0.6416(5) 0.8336(4) 0.0424(17) Uani 1 1 d . . . . .
H7 H 0.559398 0.701653 0.853312 0.051 Uiso 1 1 calc R U . . .
C8 C 0.8556(11) 0.6206(5) 0.8911(4) 0.0399(16) Uani 1 1 d . . . . .
H8 H 0.870482 0.664941 0.950514 0.048 Uiso 1 1 calc R U . . .
C9 C 1.0200(11) 0.5361(5) 0.8629(4) 0.0422(17) Uani 1 1 d . . . . .
C10 C 0.9881(11) 0.4659(5) 0.7762(4) 0.0433(17) Uani 1 1 d . . . . .
H10 H 1.095830 0.405551 0.756300 0.052 Uiso 1 1 calc R U . . .
C11 C 0.7982(11) 0.4861(5) 0.7208(4) 0.0429(17) Uani 1 1 d . . . . .
H11 H 0.774837 0.437941 0.662900 0.051 Uiso 1 1 calc R U . . .
C12 C 1.2222(11) 0.5189(5) 0.9248(4) 0.0425(17) Uani 1 1 d . . . . .
C13 C -0.3672(11) 0.1950(5) 0.2479(4) 0.0415(17) Uani 1 1 d . . . . .
C14 C -0.2013(11) 0.1476(5) 0.1849(4) 0.0458(18) Uani 1 1 d . . . . .
H14 H -0.049934 0.187574 0.181477 0.055 Uiso 1 1 calc R U . . .
C15 C -0.2591(12) 0.0429(6) 0.1282(5) 0.0501(19) Uani 1 1 d . . . . .
H15 H -0.147883 0.011416 0.084681 0.060 Uiso 1 1 calc R U . . .
C16 C -0.4775(12) -0.0182(6) 0.1331(5) 0.053(2) Uani 1 1 d . . . . .
C17 C -0.6407(11) 0.0287(6) 0.1956(4) 0.051(2) Uani 1 1 d . . . . .
H17 H -0.790322 -0.012377 0.199499 0.061 Uiso 1 1 calc R U . . .
C18 C -0.5874(11) 0.1342(5) 0.2520(4) 0.0460(18) Uani 1 1 d . . . . .
H18 H -0.701526 0.166190 0.294211 0.055 Uiso 1 1 calc R U . . .
C19 C -0.5268(13) -0.1333(6) 0.0701(5) 0.052(2) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_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 C3 1.877(5) . ?
O1 C12 1.207(7) . ?
O2 C12 1.325(6) . ?
O2 H2O 0.8400 . ?
O3 C19 1.193(8) . ?
O4 C19 1.334(8) . ?
O4 H4O 0.8400 . ?
N1 C1 1.313(7) . ?
N1 C2 1.369(7) . ?
N2 C5 1.315(7) . ?
N2 C4 1.361(7) . ?
C1 C5 1.455(8) 2_566 ?
C1 C6 1.486(8) . ?
C2 C3 1.380(7) . ?
C2 C4 1.426(7) 2_566 ?
C3 C4 1.407(8) . ?
C3 H3 0.9500 . ?
C5 C13 1.480(8) . ?
C6 C7 1.388(8) . ?
C6 C11 1.390(8) . ?
C7 C8 1.395(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(8) . ?
C9 C12 1.482(8) . ?
C10 C11 1.379(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C18 1.395(9) . ?
C13 C14 1.400(8) . ?
C14 C15 1.370(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(9) . ?
C16 C19 1.499(9) . ?
C17 C18 1.371(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C12 O2 H2O 109.5 . . ?
C19 O4 H4O 109.5 . . ?
C1 N1 C2 119.3(5) . . ?
C5 N2 C4 118.9(5) . . ?
N1 C1 C5 120.5(5) . 2_566 ?
N1 C1 C6 114.5(5) . . ?
C5 C1 C6 125.0(5) 2_566 . ?
N1 C2 C3 119.0(5) . . ?
N1 C2 C4 119.6(5) . 2_566 ?
C3 C2 C4 121.3(5) . 2_566 ?
C2 C3 C4 120.1(5) . . ?
C2 C3 Br1 119.5(4) . . ?
C4 C3 Br1 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
N2 C4 C3 120.8(5) . . ?
N2 C4 C2 120.6(5) . 2_566 ?
C3 C4 C2 118.6(5) . 2_566 ?
N2 C5 C1 120.8(5) . 2_566 ?
N2 C5 C13 115.1(5) . . ?
C1 C5 C13 124.1(5) 2_566 . ?
C7 C6 C11 118.9(5) . . ?
C7 C6 C1 123.0(5) . . ?
C11 C6 C1 117.9(5) . . ?
C6 C7 C8 120.0(5) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.9(6) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.2(5) . . ?
C8 C9 C12 119.5(5) . . ?
C10 C9 C12 121.3(5) . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C6 121.8(5) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
O1 C12 O2 123.5(5) . . ?
O1 C12 C9 123.1(5) . . ?
O2 C12 C9 113.3(5) . . ?
C18 C13 C14 119.2(6) . . ?
C18 C13 C5 120.7(6) . . ?
C14 C13 C5 120.0(6) . . ?
C15 C14 C13 119.4(6) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.3(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 119.2(6) . . ?
C17 C16 C19 122.4(7) . . ?
C15 C16 C19 118.4(6) . . ?
C18 C17 C16 120.3(6) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.6(6) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O3 C19 O4 124.0(6) . . ?
O3 C19 C16 123.7(7) . . ?
O4 C19 C16 112.3(6) . . ?

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 -1.4(10) . . . 2_566 ?
C2 N1 C1 C6 178.0(6) . . . . ?
C1 N1 C2 C3 -179.1(6) . . . . ?
C1 N1 C2 C4 -3.3(10) . . . 2_566 ?
N1 C2 C3 C4 177.7(6) . . . . ?
C4 C2 C3 C4 2.0(11) 2_566 . . . ?
N1 C2 C3 Br1 -0.8(9) . . . . ?
C4 C2 C3 Br1 -176.6(5) 2_566 . . . ?
C5 N2 C4 C3 178.3(6) . . . . ?
C5 N2 C4 C2 0.5(10) . . . 2_566 ?
C2 C3 C4 N2 -179.8(6) . . . . ?
Br1 C3 C4 N2 -1.2(9) . . . . ?
C2 C3 C4 C2 -1.9(11) . . . 2_566 ?
Br1 C3 C4 C2 176.6(5) . . . 2_566 ?
C4 N2 C5 C1 4.3(10) . . . 2_566 ?
C4 N2 C5 C13 -174.7(6) . . . . ?
N1 C1 C6 C7 -156.7(6) . . . . ?
C5 C1 C6 C7 22.7(11) 2_566 . . . ?
N1 C1 C6 C11 19.5(9) . . . . ?
C5 C1 C6 C11 -161.0(7) 2_566 . . . ?
C11 C6 C7 C8 1.3(10) . . . . ?
C1 C6 C7 C8 177.5(6) . . . . ?
C6 C7 C8 C9 2.0(10) . . . . ?
C7 C8 C9 C10 -3.8(10) . . . . ?
C7 C8 C9 C12 177.9(6) . . . . ?
C8 C9 C10 C11 2.2(10) . . . . ?
C12 C9 C10 C11 -179.4(6) . . . . ?
C9 C10 C11 C6 1.1(10) . . . . ?
C7 C6 C11 C10 -2.9(10) . . . . ?
C1 C6 C11 C10 -179.3(6) . . . . ?
C8 C9 C12 O1 -10.5(11) . . . . ?
C10 C9 C12 O1 171.2(6) . . . . ?
C8 C9 C12 O2 169.6(6) . . . . ?
C10 C9 C12 O2 -8.7(9) . . . . ?
N2 C5 C13 C18 114.6(7) . . . . ?
C1 C5 C13 C18 -64.4(10) 2_566 . . . ?
N2 C5 C13 C14 -63.0(8) . . . . ?
C1 C5 C13 C14 118.1(7) 2_566 . . . ?
C18 C13 C14 C15 0.5(10) . . . . ?
C5 C13 C14 C15 178.1(6) . . . . ?
C13 C14 C15 C16 -1.2(10) . . . . ?
C14 C15 C16 C17 1.0(11) . . . . ?
C14 C15 C16 C19 -178.9(6) . . . . ?
C15 C16 C17 C18 0.0(11) . . . . ?
C19 C16 C17 C18 179.9(7) . . . . ?
C16 C17 C18 C13 -0.8(11) . . . . ?
C14 C13 C18 C17 0.5(10) . . . . ?
C5 C13 C18 C17 -177.0(6) . . . . ?
C17 C16 C19 O3 -178.2(7) . . . . ?
C15 C16 C19 O3 1.6(11) . . . . ?
C17 C16 C19 O4 1.0(10) . . . . ?
C15 C16 C19 O4 -179.2(6) . . . . ?

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
O2 H2O O1 . . 2_867 2.674(6) 0.840 1.848 167.3 no
O4 H4O O1 . . 1_344 2.795(6) 0.840 1.963 170.5 no

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





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"4,4',4'',4'''-(5,10-dibromopyrazino[2,3-g]quinoxaline-2,3,7,8-tetrayl)tetrabenzoic acid"
_chemical_name_common            BrPQ-2a
_exptl_crystal_recrystallization_method 
'guest-release-induced structural change from BrPQ-2a'
####################################################################### 
# 
# 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_BrPQ-2
_database_code_depnum_ccdc_archive 'CCDC 2088688'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2021-07-28 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C44 H24.28 Br1.72 Cl2 N4 O8'
_chemical_formula_moiety         'C38 H20.28 Br1.72 N4 O8, C6 H4 Cl2'
_chemical_formula_weight         945.32
_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_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.5503(2)
_cell_length_b                   11.9493(5)
_cell_length_c                   15.1638(5)
_cell_angle_alpha                102.503(3)
_cell_angle_beta                 91.720(3)
_cell_angle_gamma                92.766(3)
_cell_volume                     979.86(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5407
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      31.36
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             474.48
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_T_max  0.905

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

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  PILATUS200K
_diffrn_reflns_number            16915
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_theta_max         31.368
_diffrn_reflns_theta_min         2.754
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5683
_reflns_number_gt                4813
_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          0.0668
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1507
_refine_ls_number_restraints     58
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5683
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1004P)²+0.9982P] 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         2.11
_refine_diff_density_min         -1.14
_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
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)
;
Cl Cl 0.1484 0.1585
;
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)
;
C C 0.0033 0.0016
;
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 0.69464(6) 0.23124(3) 0.51010(2) 0.02302(12) Uani 0.86 1 d . . P A 1
O1 O 1.7489(4) 0.6842(2) 0.91676(18) 0.0360(6) Uani 1 1 d . . . . .
H1O H 1.765103 0.749741 0.950967 0.043 Uiso 1 1 calc R U . . .
O2 O 1.3927(5) 0.6804(2) 0.98191(17) 0.0367(6) Uani 1 1 d . . . . .
O3 O -0.3399(4) 0.07504(17) 0.10628(13) 0.0226(4) Uani 1 1 d . . . . .
H3O H -0.453531 0.078515 0.069293 0.027 Uiso 1 1 calc R U . . .
O4 O -0.2731(4) -0.08480(16) 0.00335(13) 0.0197(4) Uani 1 1 d . . . . .
N1 N 1.1268(4) 0.19659(19) 0.63312(15) 0.0188(4) Uani 1 1 d . . . . .
N2 N 0.6147(4) 0.00275(19) 0.38028(14) 0.0172(4) Uani 1 1 d . . . . .
C1 C 1.3128(5) 0.1939(2) 0.68797(17) 0.0177(5) Uani 1 1 d . . . . .
C2 C 1.0632(5) 0.1002(2) 0.56785(16) 0.0167(5) Uani 1 1 d . . . . .
C3 C 0.8665(5) 0.0997(2) 0.50681(17) 0.0181(5) Uani 1 1 d . . . . .
H3 H 0.777129 0.166298 0.510789 0.022 Uiso 0.14 1 calc R U P A 2
C4 C 0.8025(5) 0.0004(2) 0.43999(16) 0.0175(5) Uani 1 1 d . . . . .
C5 C 0.5563(5) -0.0899(2) 0.31695(16) 0.0166(5) Uani 1 1 d . . . . .
C6 C 1.3805(5) 0.3055(2) 0.75282(17) 0.0186(5) Uani 1 1 d . . . . .
C7 C 1.6010(5) 0.3638(2) 0.74799(18) 0.0214(5) Uani 1 1 d . . . . .
H7 H 1.715305 0.330454 0.706183 0.026 Uiso 1 1 calc R U . . .
C8 C 1.6540(5) 0.4714(2) 0.80474(19) 0.0221(5) Uani 1 1 d . . . . .
H8 H 1.802803 0.512298 0.800593 0.027 Uiso 1 1 calc R U . . .
C9 C 1.4875(5) 0.5189(2) 0.86765(19) 0.0221(5) Uani 1 1 d . . . . .
C10 C 1.2682(5) 0.4593(3) 0.87398(19) 0.0244(6) Uani 1 1 d . . . . .
H10 H 1.156740 0.491064 0.917575 0.029 Uiso 1 1 calc R U . . .
C11 C 1.2140(5) 0.3531(2) 0.81597(19) 0.0223(5) Uani 1 1 d . . . . .
H11 H 1.063884 0.312778 0.819244 0.027 Uiso 1 1 calc R U . . .
C12 C 1.5334(6) 0.6348(2) 0.9284(2) 0.0259(6) Uani 1 1 d . . . . .
C13 C 0.3567(5) -0.0749(2) 0.25301(16) 0.0159(4) Uani 1 1 d . . . . .
C14 C 0.2031(5) 0.0148(2) 0.28157(17) 0.0188(5) Uani 1 1 d . . . . .
H14 H 0.227734 0.062528 0.340286 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0150(5) 0.0346(2) 0.22493(17) 0.0190(5) Uani 1 1 d . . . . .
H15 H -0.088437 0.095189 0.245034 0.023 Uiso 1 1 calc R U . . .
C16 C -0.0205(5) -0.0355(2) 0.13807(17) 0.0164(5) Uani 1 1 d . . . . .
C17 C 0.1357(5) -0.1227(2) 0.10799(16) 0.0171(5) Uani 1 1 d . . . . .
H17 H 0.113807 -0.168732 0.048542 0.021 Uiso 1 1 calc R U . . .
C18 C 0.3233(5) -0.1423(2) 0.16468(17) 0.0173(5) Uani 1 1 d . . . . .
H18 H 0.429369 -0.201547 0.143678 0.021 Uiso 1 1 calc R U . . .
C19 C -0.2227(5) -0.0180(2) 0.07670(17) 0.0169(5) Uani 1 1 d . . . . .
Cl1 Cl 0.7375(12) 0.6768(5) 0.6540(5) 0.161(3) Uani 0.5 1 d D . P B -1
Cl2 Cl 0.2095(10) 0.5494(7) 0.6610(4) 0.147(3) Uani 0.5 1 d D . P B -1
C20 C 0.594(2) 0.5752(10) 0.5686(11) 0.093(6) Uani 0.5 1 d D U P B -1
C21 C 0.366(3) 0.5082(18) 0.5679(13) 0.122(10) Uani 0.5 1 d D U P B -1
C22 C 0.247(5) 0.429(2) 0.4928(19) 0.181(13) Uani 0.5 1 d D U P B -1
H22 H 0.086950 0.397343 0.492927 0.217 Uiso 0.5 1 calc R U P B -1
C23 C 0.402(5) 0.404(3) 0.416(2) 0.203(14) Uani 0.5 1 d D U P B -1
H23 H 0.359671 0.340915 0.367240 0.244 Uiso 0.5 1 calc R U P B -1
C24 C 0.621(4) 0.4733(16) 0.4149(15) 0.108(8) Uani 0.5 1 d D U P B -1
H24 H 0.700832 0.462746 0.359433 0.129 Uiso 0.5 1 calc R U P B -1
C25 C 0.726(2) 0.5549(10) 0.4878(14) 0.097(7) Uani 0.5 1 d D U P B -1
H25 H 0.875878 0.594594 0.483746 0.117 Uiso 0.5 1 calc R U P B -1


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_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 C3 1.870(3) . ?
O1 C12 1.341(4) . ?
O1 H1O 0.8400 . ?
O2 C12 1.205(4) . ?
O3 C19 1.316(3) . ?
O3 H3O 0.8400 . ?
O4 C19 1.236(3) . ?
N1 C1 1.312(3) . ?
N1 C2 1.370(3) . ?
N2 C5 1.319(3) . ?
N2 C4 1.365(3) . ?
C1 C5 1.459(4) 2_756 ?
C1 C6 1.499(3) . ?
C2 C3 1.409(3) . ?
C2 C4 1.430(4) 2_756 ?
C3 C4 1.406(3) . ?
C3 H3 0.9500 . ?
C5 C13 1.493(3) . ?
C6 C7 1.390(4) . ?
C6 C11 1.401(4) . ?
C7 C8 1.397(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(4) . ?
C9 C12 1.493(4) . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.404(4) . ?
C13 C18 1.408(3) . ?
C14 C15 1.393(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(3) . ?
C16 C19 1.487(3) . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
Cl1 C20 1.717(13) . ?
Cl2 C21 1.674(17) . ?
C20 C25 1.427(16) . ?
C20 C21 1.463(13) . ?
C21 C22 1.433(17) . ?
C22 C23 1.453(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.441(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.396(16) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
C12 O1 H1O 109.5 . . ?
C19 O3 H3O 109.5 . . ?
C1 N1 C2 118.4(2) . . ?
C5 N2 C4 118.9(2) . . ?
N1 C1 C5 121.4(2) . 2_756 ?
N1 C1 C6 114.8(2) . . ?
C5 C1 C6 123.8(2) 2_756 . ?
N1 C2 C3 120.3(2) . . ?
N1 C2 C4 120.5(2) . 2_756 ?
C3 C2 C4 119.2(2) . 2_756 ?
C4 C3 C2 119.9(2) . . ?
C4 C3 Br1 119.01(18) . . ?
C2 C3 Br1 121.01(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N2 C4 C3 118.9(2) . . ?
N2 C4 C2 120.2(2) . 2_756 ?
C3 C4 C2 120.8(2) . 2_756 ?
N2 C5 C1 120.5(2) . 2_756 ?
N2 C5 C13 113.9(2) . . ?
C1 C5 C13 125.6(2) 2_756 . ?
C7 C6 C11 120.2(2) . . ?
C7 C6 C1 120.7(2) . . ?
C11 C6 C1 119.1(2) . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 C12 117.8(3) . . ?
C8 C9 C12 121.9(3) . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C6 120.1(3) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
O2 C12 O1 123.0(3) . . ?
O2 C12 C9 124.2(3) . . ?
O1 C12 C9 112.8(3) . . ?
C14 C13 C18 118.9(2) . . ?
C14 C13 C5 117.9(2) . . ?
C18 C13 C5 123.2(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 C19 119.1(2) . . ?
C15 C16 C19 120.9(2) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
O4 C19 O3 123.0(2) . . ?
O4 C19 C16 122.4(2) . . ?
O3 C19 C16 114.5(2) . . ?
C25 C20 C21 117.5(11) . . ?
C25 C20 Cl1 112.6(10) . . ?
C21 C20 Cl1 129.9(13) . . ?
C22 C21 C20 127.5(15) . . ?
C22 C21 Cl2 117.7(14) . . ?
C20 C21 Cl2 113.7(13) . . ?
C21 C22 C23 111.5(18) . . ?
C21 C22 H22 124.2 . . ?
C23 C22 H22 124.2 . . ?
C24 C23 C22 120(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 125.8(17) . . ?
C25 C24 H24 117.1 . . ?
C23 C24 H24 117.1 . . ?
C24 C25 C20 116.2(12) . . ?
C24 C25 H25 121.9 . . ?
C20 C25 H25 121.9 . . ?

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 -2.8(4) . . . 2_756 ?
C2 N1 C1 C6 175.8(2) . . . . ?
C1 N1 C2 C3 -179.2(3) . . . . ?
C1 N1 C2 C4 -0.1(4) . . . 2_756 ?
N1 C2 C3 C4 180.0(3) . . . . ?
C4 C2 C3 C4 0.8(4) 2_756 . . . ?
N1 C2 C3 Br1 2.4(4) . . . . ?
C4 C2 C3 Br1 -176.8(2) 2_756 . . . ?
C5 N2 C4 C3 179.2(3) . . . . ?
C5 N2 C4 C2 1.6(4) . . . 2_756 ?
C2 C3 C4 N2 -178.5(2) . . . . ?
Br1 C3 C4 N2 -0.8(4) . . . . ?
C2 C3 C4 C2 -0.8(4) . . . 2_756 ?
Br1 C3 C4 C2 176.8(2) . . . 2_756 ?
C4 N2 C5 C1 1.3(4) . . . 2_756 ?
C4 N2 C5 C13 -177.0(2) . . . . ?
N1 C1 C6 C7 -115.0(3) . . . . ?
C5 C1 C6 C7 63.5(4) 2_756 . . . ?
N1 C1 C6 C11 62.1(3) . . . . ?
C5 C1 C6 C11 -119.4(3) 2_756 . . . ?
C11 C6 C7 C8 -1.6(4) . . . . ?
C1 C6 C7 C8 175.5(2) . . . . ?
C6 C7 C8 C9 1.5(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C7 C8 C9 C12 -178.6(3) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C12 C9 C10 C11 177.3(3) . . . . ?
C9 C10 C11 C6 1.1(4) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
C1 C6 C11 C10 -176.9(3) . . . . ?
C10 C9 C12 O2 -0.5(5) . . . . ?
C8 C9 C12 O2 178.0(3) . . . . ?
C10 C9 C12 O1 179.9(3) . . . . ?
C8 C9 C12 O1 -1.6(4) . . . . ?
N2 C5 C13 C14 -20.8(4) . . . . ?
C1 C5 C13 C14 161.0(3) 2_756 . . . ?
N2 C5 C13 C18 156.0(3) . . . . ?
C1 C5 C13 C18 -22.2(4) 2_756 . . . ?
C18 C13 C14 C15 2.2(4) . . . . ?
C5 C13 C14 C15 179.2(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C17 -1.6(4) . . . . ?
C14 C15 C16 C19 178.8(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C19 C16 C17 C18 -178.7(2) . . . . ?
C16 C17 C18 C13 0.3(4) . . . . ?
C14 C13 C18 C17 -2.2(4) . . . . ?
C5 C13 C18 C17 -179.0(2) . . . . ?
C17 C16 C19 O4 7.4(4) . . . . ?
C15 C16 C19 O4 -172.9(3) . . . . ?
C17 C16 C19 O3 -171.5(2) . . . . ?
C15 C16 C19 O3 8.2(4) . . . . ?
C25 C20 C21 C22 -5(3) . . . . ?
Cl1 C20 C21 C22 175.9(18) . . . . ?
C25 C20 C21 Cl2 -173.0(9) . . . . ?
Cl1 C20 C21 Cl2 8(2) . . . . ?
C20 C21 C22 C23 11(4) . . . . ?
Cl2 C21 C22 C23 179(2) . . . . ?
C21 C22 C23 C24 -13(4) . . . . ?
C22 C23 C24 C25 11(4) . . . . ?
C23 C24 C25 C20 -4(2) . . . . ?
C21 C20 C25 C24 0.8(11) . . . . ?
Cl1 C20 C25 C24 -180.0(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 H1O O4 . . 1_766 2.799(3) 0.840 1.989 161.7 no
O3 H3O O4 . . 2_455 2.699(3) 0.840 1.862 174.1 no

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



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"4,4',4'',4'''-(5,10-dibromopyrazino[2,3-g]quinoxaline-2,3,7,8-tetrayl)tetrabenzoic acid"
_chemical_name_common            BrPQ-2
_exptl_crystal_recrystallization_method 
'guest-release-induced structural change from BrPQ-1'
