# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_gro23_04_290
_database_code_depnum_ccdc_archive 'CCDC 2420438'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_gro23_04_290        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         60 Report
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT913_gro23_04_290        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         25 Note  
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT911_gro23_04_270        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         63 Report
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT913_gro23_04_270        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         25 Note  
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT911_gro23_04_250        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         64 Report
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT913_gro23_04_250        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         24 Note  
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT911_gro23_04_230        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         61 Report
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT913_gro23_04_230        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         23 Note  
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT911_gro23_04_210        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         61 Report
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT913_gro23_04_210        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         24 Note  
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT911_gro23_04_190        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         59 Report
RESPONSE: Due to limitations with the collection strategy.
;
_vrf_PLAT913_gro23_04_190        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         18 Note  
RESPONSE: Due to limitations with the collection strategy.
;
# end Validation Reply Form


_audit_creation_date             2023-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
ryangroeneman19@webster.edu
daniel-unruh@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H11 N), C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H26 Br2 N2 O2'
_chemical_formula_weight         630.37
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.894(6)
_cell_length_b                   11.122(6)
_cell_length_c                   11.660(8)
_cell_angle_alpha                92.486(11)
_cell_angle_beta                 96.818(14)
_cell_angle_gamma                91.889(13)
_cell_volume                     1400.5(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7166
_cell_measurement_temperature    290.00
_cell_measurement_theta_max      23.639
_cell_measurement_theta_min      2.482
_shelx_estimated_absorpt_T_max   0.647
_shelx_estimated_absorpt_T_min   0.598
_exptl_absorpt_coefficient_mu    2.926
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.9281.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.163
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46592
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.419
_diffrn_ambient_temperature      290.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4020
_reflns_number_total             5673
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5673
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²+0.6704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0795
_refine_special_details          
'The ethyl moiety (C12 and C13) was positionally disordered and modeled as split sites (A and B). The refined occupancies for the A and B sites were 0.95 and 0.05, respectively. To help maintain reasonable ADP and bond length values, SIMU, RIGU, and free variable DFIX restraints were applied to the disordered sites.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C12A-C13A = C12B-C13B
 1.29377 with sigma of 0.02
 C9-C12A = C9-C12B = C14-C13A = C14-C13B
 1.4714 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C9 \\sim C12A \\sim C12B \\sim C13A \\sim C13B \\sim C14: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 C12B, C12A, C13B, C13A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C13B)=Sof(H13B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12A(H12A), C13A(H13A),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32), C13B(H13B), C12B(H12B)
6.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72539(3) -0.04379(3) -0.40311(2) 0.06141(13) Uani 1 1 d . . . . .
Br2 Br 0.32647(3) 0.24248(3) -0.30647(3) 0.06539(14) Uani 1 1 d . . . . .
O1 O 0.79794(19) -0.0016(2) -0.14682(17) 0.0676(6) Uani 1 1 d . . . . .
H1 H 0.820609 0.015441 -0.078280 0.101 Uiso 1 1 calc R U . . .
O2 O 0.4507(2) 0.2282(2) -0.06268(18) 0.0734(6) Uani 1 1 d . . . . .
H2 H 0.492621 0.237900 0.000477 0.110 Uiso 1 1 calc R U . . .
N1 N 0.8824(2) 0.0574(3) 0.0754(2) 0.0672(7) Uani 1 1 d . . . . .
C1 C 0.6422(3) 0.0448(2) -0.2947(2) 0.0472(6) Uani 1 1 d . . . . .
C2 C 0.5347(3) 0.0992(2) -0.3323(2) 0.0481(7) Uani 1 1 d . . . . .
H2A H 0.504236 0.094352 -0.410416 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4716(2) 0.1614(2) -0.2540(2) 0.0481(6) Uani 1 1 d . . . . .
C4 C 0.5158(3) 0.1686(3) -0.1369(2) 0.0530(7) Uani 1 1 d . . . . .
C5 C 0.6246(3) 0.1129(3) -0.1015(2) 0.0557(7) Uani 1 1 d . . . . .
H5 H 0.654410 0.116682 -0.023221 0.067 Uiso 1 1 calc R U . . .
C6 C 0.6911(3) 0.0516(3) -0.1788(2) 0.0500(7) Uani 1 1 d . . . . .
C7 C 0.8472(3) -0.0064(3) 0.1590(3) 0.0785(10) Uani 1 1 d . . . . .
H7 H 0.803737 -0.079140 0.138962 0.094 Uiso 1 1 calc R U . . .
C8 C 0.8709(4) 0.0283(3) 0.2741(3) 0.0831(11) Uani 1 1 d . . . . .
H8 H 0.843765 -0.021068 0.329117 0.100 Uiso 1 1 calc R U . . .
C9 C 0.9340(3) 0.1343(3) 0.3091(3) 0.0604(8) Uani 1 1 d D U . . .
C10 C 0.9750(3) 0.1990(3) 0.2231(3) 0.0704(9) Uani 1 1 d . . . . .
H10 H 1.021085 0.270662 0.241249 0.084 Uiso 1 1 calc R U . . .
C11 C 0.9480(3) 0.1579(4) 0.1099(3) 0.0804(10) Uani 1 1 d . . . . .
H11 H 0.977661 0.203654 0.053440 0.097 Uiso 1 1 calc R U . . .
C12A C 0.9513(3) 0.1716(3) 0.4325(3) 0.0652(10) Uani 0.947(6) 1 d D U P A 1
H12A H 0.921250 0.118194 0.482704 0.078 Uiso 0.947(6) 1 calc R U P A 1
C13A C 1.0042(3) 0.2714(3) 0.4789(3) 0.0611(10) Uani 0.947(6) 1 d D U P A 1
H13A H 1.039916 0.322286 0.429854 0.073 Uiso 0.947(6) 1 calc R U P A 1
C14 C 1.0132(3) 0.3118(3) 0.6018(2) 0.0586(8) Uani 1 1 d D U . . .
C15 C 0.9626(3) 0.2477(4) 0.6845(3) 0.0781(10) Uani 1 1 d . . . . .
H15 H 0.922100 0.173660 0.663536 0.094 Uiso 1 1 calc R U . . .
C16 C 0.9709(4) 0.2909(5) 0.7962(3) 0.0987(13) Uani 1 1 d . . . . .
H16 H 0.935850 0.246142 0.850424 0.118 Uiso 1 1 calc R U . . .
C17 C 1.0293(4) 0.3981(5) 0.8295(3) 0.0985(15) Uani 1 1 d . . . . .
H17 H 1.033914 0.426886 0.906057 0.118 Uiso 1 1 calc R U . . .
C18 C 1.0815(4) 0.4638(4) 0.7504(4) 0.0911(13) Uani 1 1 d . . . . .
H18 H 1.122865 0.537054 0.773175 0.109 Uiso 1 1 calc R U . . .
C19 C 1.0729(3) 0.4212(3) 0.6359(3) 0.0725(9) Uani 1 1 d . . . . .
H19 H 1.107455 0.466599 0.581937 0.087 Uiso 1 1 calc R U . . .
N2 N 0.5698(2) 0.2659(2) 0.1521(2) 0.0619(7) Uani 1 1 d . . . . .
C20 C 0.5839(3) 0.1840(3) 0.2320(3) 0.0683(9) Uani 1 1 d . . . . .
H20 H 0.572456 0.103160 0.207984 0.082 Uiso 1 1 calc R U . . .
C21 C 0.6143(3) 0.2121(3) 0.3475(3) 0.0663(9) Uani 1 1 d . . . . .
H21 H 0.624611 0.150685 0.399039 0.080 Uiso 1 1 calc R U . . .
C22 C 0.6299(3) 0.3310(3) 0.3882(2) 0.0544(7) Uani 1 1 d . . . . .
C23 C 0.6150(3) 0.4166(3) 0.3044(3) 0.0617(8) Uani 1 1 d . . . . .
H23 H 0.624914 0.498121 0.325857 0.074 Uiso 1 1 calc R U . . .
C24 C 0.5859(3) 0.3807(3) 0.1906(3) 0.0641(8) Uani 1 1 d . . . . .
H24 H 0.576787 0.440003 0.136691 0.077 Uiso 1 1 calc R U . . .
C25 C 0.6582(3) 0.3619(3) 0.5124(3) 0.0607(8) Uani 1 1 d . . . . .
H25 H 0.669657 0.298089 0.561014 0.073 Uiso 1 1 calc R U . . .
C26 C 0.6690(3) 0.4707(3) 0.5615(3) 0.0605(8) Uani 1 1 d . . . . .
H26 H 0.660898 0.533647 0.511483 0.073 Uiso 1 1 calc R U . . .
C27 C 0.6922(3) 0.5058(3) 0.6849(3) 0.0577(8) Uani 1 1 d . . . . .
C28 C 0.6905(3) 0.4234(3) 0.7717(3) 0.0683(9) Uani 1 1 d . . . . .
H28 H 0.677510 0.341737 0.751728 0.082 Uiso 1 1 calc R U . . .
C29 C 0.7079(3) 0.4618(4) 0.8863(3) 0.0815(10) Uani 1 1 d . . . . .
H29 H 0.706725 0.405717 0.943081 0.098 Uiso 1 1 calc R U . . .
C30 C 0.7271(3) 0.5819(4) 0.9181(3) 0.0865(12) Uani 1 1 d . . . . .
H30 H 0.737578 0.607078 0.995868 0.104 Uiso 1 1 calc R U . . .
C31 C 0.7306(3) 0.6646(4) 0.8341(4) 0.0843(11) Uani 1 1 d . . . . .
H31 H 0.744994 0.745904 0.855131 0.101 Uiso 1 1 calc R U . . .
C32 C 0.7129(3) 0.6273(3) 0.7188(3) 0.0709(9) Uani 1 1 d . . . . .
H32 H 0.714749 0.684042 0.662713 0.085 Uiso 1 1 calc R U . . .
C13B C 0.969(6) 0.225(5) 0.505(3) 0.058(6) Uani 0.053(6) 1 d D U P A 2
H13B H 0.923104 0.159371 0.525289 0.069 Uiso 0.053(6) 1 calc R U P A 2
C12B C 0.985(5) 0.227(4) 0.398(3) 0.057(6) Uani 0.053(6) 1 d D U P A 2
H12B H 1.030964 0.291284 0.374146 0.068 Uiso 0.053(6) 1 calc R U P A 2


_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 1.900(3) . ?
Br2 C3 1.897(3) . ?
O1 H1 0.8200 . ?
O1 C6 1.343(3) . ?
O2 H2 0.8200 . ?
O2 C4 1.348(3) . ?
N1 C7 1.316(4) . ?
N1 C11 1.328(5) . ?
C1 C2 1.371(4) . ?
C1 C6 1.391(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.382(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(5) . ?
C9 C10 1.368(4) . ?
C9 C12A 1.468(4) . ?
C9 C12B 1.47(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(5) . ?
C11 H11 0.9300 . ?
C12A H12A 0.9300 . ?
C12A C13A 1.300(5) . ?
C13A H13A 0.9300 . ?
C13A C14 1.473(4) . ?
C14 C15 1.380(5) . ?
C14 C19 1.380(4) . ?
C14 C13B 1.47(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.352(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(5) . ?
C19 H19 0.9300 . ?
N2 C20 1.331(4) . ?
N2 C24 1.334(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.368(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(4) . ?
C22 C23 1.393(4) . ?
C22 C25 1.467(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.365(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.312(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.465(4) . ?
C27 C28 1.396(4) . ?
C27 C32 1.394(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.375(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.372(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.376(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.379(5) . ?
C32 H32 0.9300 . ?
C13B H13B 0.9300 . ?
C13B C12B 1.29(3) . ?
C12B H12B 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
C6 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 115.2(3) . . ?
C2 C1 Br1 119.3(2) . . ?
C2 C1 C6 121.5(2) . . ?
C6 C1 Br1 119.2(2) . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.9(2) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 Br2 120.0(2) . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 Br2 119.4(2) . . ?
O2 C4 C3 119.0(3) . . ?
O2 C4 C5 122.7(3) . . ?
C5 C4 C3 118.3(3) . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.3(3) . . ?
C6 C5 H5 118.8 . . ?
O1 C6 C1 119.1(2) . . ?
O1 C6 C5 123.5(2) . . ?
C1 C6 C5 117.4(3) . . ?
N1 C7 H7 118.1 . . ?
N1 C7 C8 123.7(3) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 115.7(3) . . ?
C8 C9 C12A 119.3(3) . . ?
C8 C9 C12B 153(2) . . ?
C10 C9 C12A 125.0(3) . . ?
C10 C9 C12B 91(2) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
N1 C11 C10 124.5(3) . . ?
N1 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
C9 C12A H12A 116.6 . . ?
C13A C12A C9 126.8(4) . . ?
C13A C12A H12A 116.6 . . ?
C12A C13A H13A 116.8 . . ?
C12A C13A C14 126.3(4) . . ?
C14 C13A H13A 116.8 . . ?
C15 C14 C13A 123.6(3) . . ?
C15 C14 C19 117.9(3) . . ?
C15 C14 C13B 95(2) . . ?
C19 C14 C13A 118.5(3) . . ?
C19 C14 C13B 147(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.9(4) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 C18 120.4(4) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C20 N2 C24 116.1(3) . . ?
N2 C20 H20 118.2 . . ?
N2 C20 C21 123.7(3) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 115.6(3) . . ?
C21 C22 C25 120.9(3) . . ?
C23 C22 C25 123.5(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
N2 C24 C23 124.0(3) . . ?
N2 C24 H24 118.0 . . ?
C23 C24 H24 118.0 . . ?
C22 C25 H25 116.8 . . ?
C26 C25 C22 126.4(3) . . ?
C26 C25 H25 116.8 . . ?
C25 C26 H26 115.8 . . ?
C25 C26 C27 128.4(3) . . ?
C27 C26 H26 115.8 . . ?
C28 C27 C26 123.0(3) . . ?
C32 C27 C26 119.3(3) . . ?
C32 C27 C28 117.7(3) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.6(3) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.9(4) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.2 . . ?
C29 C30 C31 119.5(3) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 H32 119.5 . . ?
C31 C32 C27 121.1(4) . . ?
C31 C32 H32 119.5 . . ?
C14 C13B H13B 115.0 . . ?
C12B C13B C14 130(4) . . ?
C12B C13B H13B 115.0 . . ?
C9 C12B H12B 117.8 . . ?
C13B C12B C9 124(3) . . ?
C13B C12B H12B 117.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.87 2.690(3) 176.3 . yes
O2 H2 N2 0.82 1.87 2.689(3) 172.7 . yes

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
Br1 C1 C2 C3 178.4(2) . . . . ?
Br1 C1 C6 O1 2.0(4) . . . . ?
Br1 C1 C6 C5 -177.3(2) . . . . ?
Br2 C3 C4 O2 3.3(4) . . . . ?
Br2 C3 C4 C5 -177.3(2) . . . . ?
O2 C4 C5 C6 180.0(3) . . . . ?
N1 C7 C8 C9 0.2(6) . . . . ?
C1 C2 C3 Br2 177.4(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C1 C6 O1 -178.8(3) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C2 C3 C4 O2 -178.9(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 O1 178.9(3) . . . . ?
C4 C5 C6 C1 -1.8(4) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C7 N1 C11 C10 -2.8(5) . . . . ?
C7 C8 C9 C10 -2.6(5) . . . . ?
C7 C8 C9 C12A 176.5(4) . . . . ?
C7 C8 C9 C12B 175(5) . . . . ?
C8 C9 C10 C11 2.3(5) . . . . ?
C8 C9 C12A C13A -177.0(4) . . . . ?
C8 C9 C12B C13B -3(10) . . . . ?
C9 C10 C11 N1 0.4(6) . . . . ?
C9 C12A C13A C14 175.3(3) . . . . ?
C10 C9 C12A C13A 2.0(6) . . . . ?
C10 C9 C12B C13B 175(6) . . . . ?
C11 N1 C7 C8 2.4(5) . . . . ?
C12A C9 C10 C11 -176.8(3) . . . . ?
C12A C13A C14 C15 -1.5(6) . . . . ?
C12A C13A C14 C19 -179.9(3) . . . . ?
C13A C14 C15 C16 -178.2(3) . . . . ?
C13A C14 C19 C18 178.8(3) . . . . ?
C14 C15 C16 C17 -0.2(6) . . . . ?
C14 C13B C12B C9 -179(5) . . . . ?
C15 C14 C19 C18 0.4(5) . . . . ?
C15 C14 C13B C12B -179(7) . . . . ?
C15 C16 C17 C18 -0.4(7) . . . . ?
C16 C17 C18 C19 0.9(6) . . . . ?
C17 C18 C19 C14 -0.9(5) . . . . ?
C19 C14 C15 C16 0.2(5) . . . . ?
C19 C14 C13B C12B 5(11) . . . . ?
N2 C20 C21 C22 1.4(5) . . . . ?
C20 N2 C24 C23 -0.1(5) . . . . ?
C20 C21 C22 C23 -1.2(5) . . . . ?
C20 C21 C22 C25 177.8(3) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C21 C22 C25 C26 -176.5(3) . . . . ?
C22 C23 C24 N2 0.1(5) . . . . ?
C22 C25 C26 C27 177.3(3) . . . . ?
C23 C22 C25 C26 2.5(5) . . . . ?
C24 N2 C20 C21 -0.6(5) . . . . ?
C25 C22 C23 C24 -178.5(3) . . . . ?
C25 C26 C27 C28 -8.6(5) . . . . ?
C25 C26 C27 C32 173.6(3) . . . . ?
C26 C27 C28 C29 -177.3(3) . . . . ?
C26 C27 C32 C31 177.6(3) . . . . ?
C27 C28 C29 C30 0.1(5) . . . . ?
C28 C27 C32 C31 -0.2(5) . . . . ?
C28 C29 C30 C31 -0.9(6) . . . . ?
C29 C30 C31 C32 1.1(6) . . . . ?
C30 C31 C32 C27 -0.5(5) . . . . ?
C32 C27 C28 C29 0.5(5) . . . . ?
C13B C14 C15 C16 -177(3) . . . . ?
C13B C14 C19 C18 175(5) . . . . ?
C12B C9 C10 C11 -177(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_04_230
_database_code_depnum_ccdc_archive 'CCDC 2420441'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H11 N), C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H26 Br2 N2 O2'
_chemical_formula_weight         630.37
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.797(5)
_cell_length_b                   11.105(5)
_cell_length_c                   11.636(7)
_cell_angle_alpha                92.156(12)
_cell_angle_beta                 96.727(11)
_cell_angle_gamma                91.992(11)
_cell_volume                     1383.5(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8399
_cell_measurement_temperature    230.00
_cell_measurement_theta_max      23.682
_cell_measurement_theta_min      2.493
_shelx_estimated_absorpt_T_max   0.644
_shelx_estimated_absorpt_T_min   0.594
_exptl_absorpt_coefficient_mu    2.962
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0714 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.9169.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.163
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46047
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.435
_diffrn_ambient_temperature      230.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4325
_reflns_number_total             5602
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0158(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+0.4212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72622(2) -0.04496(2) -0.40298(2) 0.04479(10) Uani 1 1 d . . . . .
Br2 Br 0.32458(2) 0.24358(2) -0.30760(2) 0.04783(11) Uani 1 1 d . . . . .
O1 O 0.79948(16) -0.00219(17) -0.14643(14) 0.0498(5) Uani 1 1 d . . . . .
H1 H 0.822860 0.015247 -0.077114 0.075 Uiso 1 1 calc R U . . .
O2 O 0.44916(17) 0.22854(19) -0.06316(16) 0.0549(5) Uani 1 1 d . . . . .
H2 H 0.491712 0.238472 0.000898 0.082 Uiso 1 1 calc R U . . .
N1 N 0.8842(2) 0.0581(2) 0.07554(18) 0.0506(6) Uani 1 1 d . . . . .
C1 C 0.6424(2) 0.0444(2) -0.29513(19) 0.0354(5) Uani 1 1 d . . . . .
C2 C 0.5337(2) 0.0992(2) -0.3332(2) 0.0361(5) Uani 1 1 d . . . . .
H2A H 0.502588 0.094388 -0.412203 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4705(2) 0.1615(2) -0.2545(2) 0.0364(5) Uani 1 1 d . . . . .
C4 C 0.5149(2) 0.1685(2) -0.1370(2) 0.0400(6) Uani 1 1 d . . . . .
C5 C 0.6246(2) 0.1123(2) -0.1009(2) 0.0415(6) Uani 1 1 d . . . . .
H5 H 0.654725 0.115645 -0.021662 0.050 Uiso 1 1 calc R U . . .
C6 C 0.6915(2) 0.0511(2) -0.1785(2) 0.0382(5) Uani 1 1 d . . . . .
C7 C 0.8483(3) -0.0074(3) 0.1589(3) 0.0579(8) Uani 1 1 d . . . . .
H7 H 0.804562 -0.081155 0.138186 0.070 Uiso 1 1 calc R U . . .
C8 C 0.8717(3) 0.0265(3) 0.2748(2) 0.0605(8) Uani 1 1 d . . . . .
H8 H 0.844287 -0.024166 0.330374 0.073 Uiso 1 1 calc R U . . .
C9 C 0.9350(2) 0.1340(2) 0.3099(2) 0.0439(6) Uani 1 1 d . . . . .
C10 C 0.9756(3) 0.2006(3) 0.2229(2) 0.0502(7) Uani 1 1 d . . . . .
H10 H 1.021251 0.273777 0.241386 0.060 Uiso 1 1 calc R U . . .
C11 C 0.9494(3) 0.1603(3) 0.1095(2) 0.0585(8) Uani 1 1 d . . . . .
H11 H 0.979218 0.207283 0.052290 0.070 Uiso 1 1 calc R U . . .
C12 C 0.9521(3) 0.1717(3) 0.4328(2) 0.0498(7) Uani 1 1 d . . . . .
H12 H 0.922017 0.117184 0.483829 0.060 Uiso 1 1 calc R U . . .
C13 C 1.0045(2) 0.2729(2) 0.4799(2) 0.0448(6) Uani 1 1 d . . . . .
H13 H 1.040408 0.325036 0.430055 0.054 Uiso 1 1 calc R U . . .
C14 C 1.0129(2) 0.3134(2) 0.6023(2) 0.0434(6) Uani 1 1 d . . . . .
C15 C 0.9613(3) 0.2469(3) 0.6846(2) 0.0566(7) Uani 1 1 d . . . . .
H15 H 0.920513 0.171963 0.662742 0.068 Uiso 1 1 calc R U . . .
C16 C 0.9691(3) 0.2895(3) 0.7978(3) 0.0705(9) Uani 1 1 d . . . . .
H16 H 0.933220 0.243581 0.852430 0.085 Uiso 1 1 calc R U . . .
C17 C 1.0286(3) 0.3981(4) 0.8318(3) 0.0722(10) Uani 1 1 d . . . . .
H17 H 1.033105 0.426801 0.909244 0.087 Uiso 1 1 calc R U . . .
C18 C 1.0814(3) 0.4648(3) 0.7522(3) 0.0650(9) Uani 1 1 d . . . . .
H18 H 1.123372 0.538939 0.775307 0.078 Uiso 1 1 calc R U . . .
C19 C 1.0730(3) 0.4230(3) 0.6373(2) 0.0526(7) Uani 1 1 d . . . . .
H19 H 1.108516 0.469632 0.582947 0.063 Uiso 1 1 calc R U . . .
N2 N 0.5700(2) 0.2656(2) 0.15137(18) 0.0448(5) Uani 1 1 d . . . . .
C20 C 0.5843(3) 0.1825(2) 0.2315(2) 0.0504(7) Uani 1 1 d . . . . .
H20 H 0.572981 0.100857 0.206973 0.061 Uiso 1 1 calc R U . . .
C21 C 0.6146(3) 0.2099(2) 0.3474(2) 0.0488(7) Uani 1 1 d . . . . .
H21 H 0.624466 0.147555 0.399723 0.059 Uiso 1 1 calc R U . . .
C22 C 0.6308(2) 0.3302(2) 0.3882(2) 0.0406(6) Uani 1 1 d . . . . .
C23 C 0.6156(2) 0.4164(2) 0.3034(2) 0.0452(6) Uani 1 1 d . . . . .
H23 H 0.625586 0.498943 0.324820 0.054 Uiso 1 1 calc R U . . .
C24 C 0.5863(3) 0.3807(3) 0.1897(2) 0.0482(6) Uani 1 1 d . . . . .
H24 H 0.576902 0.440836 0.134947 0.058 Uiso 1 1 calc R U . . .
C25 C 0.6594(2) 0.3604(2) 0.5120(2) 0.0448(6) Uani 1 1 d . . . . .
H25 H 0.672363 0.295823 0.561333 0.054 Uiso 1 1 calc R U . . .
C26 C 0.6686(2) 0.4707(2) 0.5612(2) 0.0446(6) Uani 1 1 d . . . . .
H26 H 0.659316 0.534516 0.510451 0.053 Uiso 1 1 calc R U . . .
C27 C 0.6916(2) 0.5050(2) 0.6846(2) 0.0434(6) Uani 1 1 d . . . . .
C28 C 0.6894(3) 0.4222(3) 0.7716(2) 0.0504(7) Uani 1 1 d . . . . .
H28 H 0.676109 0.339598 0.751488 0.061 Uiso 1 1 calc R U . . .
C29 C 0.7064(3) 0.4602(3) 0.8869(3) 0.0614(8) Uani 1 1 d . . . . .
H29 H 0.704457 0.403320 0.944580 0.074 Uiso 1 1 calc R U . . .
C30 C 0.7262(3) 0.5809(3) 0.9182(3) 0.0650(9) Uani 1 1 d . . . . .
H30 H 0.737140 0.606274 0.996829 0.078 Uiso 1 1 calc R U . . .
C31 C 0.7299(3) 0.6641(3) 0.8341(3) 0.0628(9) Uani 1 1 d . . . . .
H31 H 0.744378 0.746305 0.855335 0.075 Uiso 1 1 calc R U . . .
C32 C 0.7123(3) 0.6272(2) 0.7177(3) 0.0540(7) Uani 1 1 d . . . . .
H32 H 0.714246 0.684793 0.660757 0.065 Uiso 1 1 calc R U . . .


_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 1.901(2) . ?
Br2 C3 1.900(2) . ?
O1 H1 0.8300 . ?
O1 C6 1.346(3) . ?
O2 H2 0.8300 . ?
O2 C4 1.349(3) . ?
N1 C7 1.320(4) . ?
N1 C11 1.336(4) . ?
C1 C2 1.375(3) . ?
C1 C6 1.396(3) . ?
C2 H2A 0.9400 . ?
C2 C3 1.384(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.387(3) . ?
C5 H5 0.9400 . ?
C5 C6 1.393(3) . ?
C7 H7 0.9400 . ?
C7 C8 1.378(4) . ?
C8 H8 0.9400 . ?
C8 C9 1.378(4) . ?
C9 C10 1.379(4) . ?
C9 C12 1.463(4) . ?
C10 H10 0.9400 . ?
C10 C11 1.372(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C12 C13 1.311(4) . ?
C13 H13 0.9400 . ?
C13 C14 1.469(4) . ?
C14 C15 1.386(4) . ?
C14 C19 1.384(4) . ?
C15 H15 0.9400 . ?
C15 C16 1.375(4) . ?
C16 H16 0.9400 . ?
C16 C17 1.369(5) . ?
C17 H17 0.9400 . ?
C17 C18 1.370(5) . ?
C18 H18 0.9400 . ?
C18 C19 1.390(4) . ?
C19 H19 0.9400 . ?
N2 C20 1.335(3) . ?
N2 C24 1.337(3) . ?
C20 H20 0.9400 . ?
C20 C21 1.370(4) . ?
C21 H21 0.9400 . ?
C21 C22 1.399(3) . ?
C22 C23 1.401(4) . ?
C22 C25 1.461(4) . ?
C23 H23 0.9400 . ?
C23 C24 1.364(4) . ?
C24 H24 0.9400 . ?
C25 H25 0.9400 . ?
C25 C26 1.327(3) . ?
C26 H26 0.9400 . ?
C26 C27 1.463(4) . ?
C27 C28 1.394(4) . ?
C27 C32 1.400(4) . ?
C28 H28 0.9400 . ?
C28 C29 1.381(4) . ?
C29 H29 0.9400 . ?
C29 C30 1.378(4) . ?
C30 H30 0.9400 . ?
C30 C31 1.374(5) . ?
C31 H31 0.9400 . ?
C31 C32 1.389(4) . ?
C32 H32 0.9400 . ?

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 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 116.0(2) . . ?
C2 C1 Br1 119.39(17) . . ?
C2 C1 C6 121.5(2) . . ?
C6 C1 Br1 119.14(18) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 Br2 119.72(18) . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 Br2 119.38(18) . . ?
O2 C4 C3 118.8(2) . . ?
O2 C4 C5 122.8(2) . . ?
C5 C4 C3 118.4(2) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
O1 C6 C1 119.0(2) . . ?
O1 C6 C5 123.4(2) . . ?
C5 C6 C1 117.7(2) . . ?
N1 C7 H7 118.3 . . ?
N1 C7 C8 123.5(3) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 115.8(2) . . ?
C8 C9 C12 119.7(2) . . ?
C10 C9 C12 124.5(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
N1 C11 C10 123.9(3) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C9 C12 H12 116.3 . . ?
C13 C12 C9 127.5(3) . . ?
C13 C12 H12 116.3 . . ?
C12 C13 H13 116.6 . . ?
C12 C13 C14 126.8(3) . . ?
C14 C13 H13 116.6 . . ?
C15 C14 C13 122.7(2) . . ?
C19 C14 C13 119.1(3) . . ?
C19 C14 C15 118.2(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.7(3) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C20 N2 C24 116.4(2) . . ?
N2 C20 H20 118.2 . . ?
N2 C20 C21 123.6(2) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 115.5(2) . . ?
C21 C22 C25 120.8(2) . . ?
C23 C22 C25 123.7(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 120.0 . . ?
N2 C24 C23 124.1(3) . . ?
N2 C24 H24 118.0 . . ?
C23 C24 H24 118.0 . . ?
C22 C25 H25 117.0 . . ?
C26 C25 C22 126.0(3) . . ?
C26 C25 H25 117.0 . . ?
C25 C26 H26 116.0 . . ?
C25 C26 C27 128.0(3) . . ?
C27 C26 H26 116.0 . . ?
C28 C27 C26 123.2(2) . . ?
C28 C27 C32 118.1(2) . . ?
C32 C27 C26 118.7(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.7(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.3(3) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 H32 119.7 . . ?
C31 C32 C27 120.6(3) . . ?
C31 C32 H32 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.86 2.689(3) 176.6 . yes
O2 H2 N2 0.83 1.86 2.688(3) 173.3 . yes

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
Br1 C1 C2 C3 178.21(17) . . . . ?
Br1 C1 C6 O1 2.4(3) . . . . ?
Br1 C1 C6 C5 -176.94(18) . . . . ?
Br2 C3 C4 O2 3.3(3) . . . . ?
Br2 C3 C4 C5 -177.21(19) . . . . ?
O2 C4 C5 C6 -179.7(2) . . . . ?
N1 C7 C8 C9 0.3(5) . . . . ?
C1 C2 C3 Br2 177.14(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C1 C6 O1 -178.7(2) . . . . ?
C2 C1 C6 C5 2.0(4) . . . . ?
C2 C3 C4 O2 -178.9(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 O1 178.6(2) . . . . ?
C4 C5 C6 C1 -2.0(4) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C7 N1 C11 C10 -2.6(4) . . . . ?
C7 C8 C9 C10 -2.2(4) . . . . ?
C7 C8 C9 C12 176.2(3) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
C8 C9 C12 C13 -176.7(3) . . . . ?
C9 C10 C11 N1 0.7(5) . . . . ?
C9 C12 C13 C14 175.2(3) . . . . ?
C10 C9 C12 C13 1.6(5) . . . . ?
C11 N1 C7 C8 2.0(4) . . . . ?
C12 C9 C10 C11 -176.7(3) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C12 C13 C14 C19 179.4(3) . . . . ?
C13 C14 C15 C16 -178.6(3) . . . . ?
C13 C14 C19 C18 179.2(3) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C14 C19 C18 0.2(4) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C17 C18 C19 C14 -0.8(4) . . . . ?
C19 C14 C15 C16 0.4(4) . . . . ?
N2 C20 C21 C22 0.8(4) . . . . ?
C20 N2 C24 C23 -0.1(4) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
C20 C21 C22 C25 178.1(3) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C21 C22 C25 C26 -175.3(3) . . . . ?
C22 C23 C24 N2 0.2(4) . . . . ?
C22 C25 C26 C27 177.1(2) . . . . ?
C23 C22 C25 C26 3.5(4) . . . . ?
C24 N2 C20 C21 -0.3(4) . . . . ?
C25 C22 C23 C24 -178.6(2) . . . . ?
C25 C26 C27 C28 -9.7(4) . . . . ?
C25 C26 C27 C32 172.8(3) . . . . ?
C26 C27 C28 C29 -177.2(3) . . . . ?
C26 C27 C32 C31 177.6(3) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C28 C27 C32 C31 0.0(4) . . . . ?
C28 C29 C30 C31 -0.4(5) . . . . ?
C29 C30 C31 C32 0.8(5) . . . . ?
C30 C31 C32 C27 -0.5(4) . . . . ?
C32 C27 C28 C29 0.3(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_08_250
_database_code_depnum_ccdc_archive 'CCDC 2420452'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10.22 N, C13 H10.30 N, C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H24.52 Br2 N2 O2'
_chemical_formula_weight         628.88
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8860(6)
_cell_length_b                   11.0501(5)
_cell_length_c                   11.7037(7)
_cell_angle_alpha                91.998(2)
_cell_angle_beta                 97.416(2)
_cell_angle_gamma                91.813(2)
_cell_volume                     1394.30(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    250.00
_cell_measurement_theta_max      24.066
_cell_measurement_theta_min      2.591
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.939
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0841 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8620.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             633
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.155
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            50027
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         2.405
_diffrn_ambient_temperature      250.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4819
_reflns_number_total             6848
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6848
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+0.4378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0870
_refine_special_details          
'In this structure, there was a mixture of 4-phenylethynyl)pyridine (A sites) and 4-stilbazole (B-sites). At this temperature, the refined occupancies of the A and B sites for molecules containing nitrogen atom N1 or N2 were 0.39:0.61 and 0.35:0.65, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, SIMU, RIGU, free variable DFIX and AFIX restraints and constraints were applied where necessary.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C12A-C13A = C25A-C26A
 1.1409 with sigma of 0.02
 C12B-C13B = C25B-C26B
 1.35041 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25A \\sim C25B \\sim C26A \\sim C26B: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.02 within 2A
C9 \\sim C12B \\sim C12A \\sim C13A \\sim C13B \\sim C14A \\sim C15A \\sim C16A
\\sim C17A \\sim C18A \\sim C19A \\sim C14B \\sim C15B \\sim C17B \\sim C16B
\\sim C18B \\sim C19B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C25B, C25A, C26A, C26B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 C9, C12B, C12A, C13A, C13B, C14A, C15A, C16A, C17A, C18A, C19A, C14B, C15B,
 C17B, C16B, C18B, C19B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C19B)=Sof(H19B)=
 Sof(C18B)=Sof(H18B)=Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=
 Sof(H15B)=1-FVAR(1)
 Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=FVAR(1)
 Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=1-FVAR(2)
 Sof(C25A)=Sof(C26A)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C19A(H19A), C18A(H18A),
 C17A(H17A), C16A(H16A), C15A(H15A), C12B(H12B), C13B(H13B), C19B(H19B),
 C18B(H18B), C17B(H17B), C16B(H16B), C15B(H15B), C20(H20), C21(H21), C23(H23),
 C24(H24), C25B(H25B), C26B(H26B), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32)
6.b Fitted hexagon refined as free rotating group:
 C14A(C19A,C18A,C17A,C16A,C15A), C14B(C19B,C18B,C17B,C16B,C15B)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72796(2) -0.04176(2) -0.40242(2) 0.05895(11) Uani 1 1 d . . . . .
Br2 Br 0.32579(2) 0.24307(2) -0.31205(2) 0.06101(11) Uani 1 1 d . . . . .
O1 O 0.79620(16) -0.00588(17) -0.14559(14) 0.0620(5) Uani 1 1 d . . . . .
H1 H 0.818560 0.010212 -0.075159 0.093 Uiso 1 1 calc R U . . .
O2 O 0.44669(17) 0.22343(19) -0.06704(16) 0.0682(5) Uani 1 1 d . . . . .
H2 H 0.487687 0.229449 -0.001058 0.102 Uiso 1 1 calc R U . . .
N1 N 0.8796(2) 0.0500(2) 0.07693(18) 0.0623(6) Uani 1 1 d . . . . .
C1 C 0.6428(2) 0.04455(19) -0.29586(18) 0.0449(5) Uani 1 1 d . . . . .
C2 C 0.5348(2) 0.10048(18) -0.33491(19) 0.0463(5) Uani 1 1 d . . . . .
H2A H 0.504627 0.097496 -0.414857 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4706(2) 0.16098(19) -0.25723(19) 0.0452(5) Uani 1 1 d . . . . .
C4 C 0.5128(2) 0.1651(2) -0.1401(2) 0.0488(5) Uani 1 1 d . . . . .
C5 C 0.6217(2) 0.1077(2) -0.10275(19) 0.0513(6) Uani 1 1 d . . . . .
H5 H 0.650786 0.109099 -0.022595 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6894(2) 0.0484(2) -0.17911(19) 0.0474(5) Uani 1 1 d . . . . .
C7 C 0.8449(3) -0.0115(3) 0.1627(2) 0.0692(7) Uani 1 1 d . . . . .
H7 H 0.799212 -0.085943 0.144766 0.083 Uiso 1 1 calc R U . . .
C8 C 0.8713(3) 0.0265(3) 0.2765(2) 0.0717(8) Uani 1 1 d . . . . .
H8 H 0.844989 -0.021972 0.334905 0.086 Uiso 1 1 calc R U . . .
C9 C 0.9358(2) 0.1346(2) 0.3063(2) 0.0558(6) Uani 1 1 d . U . . .
C10 C 0.9749(3) 0.1974(3) 0.2173(2) 0.0677(7) Uani 1 1 d . . . . .
H10 H 1.021529 0.271628 0.232640 0.081 Uiso 1 1 calc R U . . .
C11 C 0.9458(3) 0.1518(3) 0.1059(2) 0.0725(8) Uani 1 1 d . . . . .
H11 H 0.974915 0.195980 0.046003 0.087 Uiso 1 1 calc R U . . .
C12A C 0.9700(15) 0.1962(14) 0.4153(12) 0.060(2) Uani 0.391(12) 1 d D U P A 1
C13A C 0.9859(12) 0.2413(12) 0.5051(10) 0.059(2) Uani 0.391(12) 1 d D U P A 1
C14A C 1.0075(14) 0.3062(10) 0.6092(6) 0.0579(17) Uani 0.391(12) 1 d G U P A 1
C19A C 1.0702(13) 0.4182(10) 0.6138(7) 0.0634(18) Uani 0.391(12) 1 d G U P A 1
H19A H 1.098242 0.448391 0.546272 0.076 Uiso 0.391(12) 1 calc R U P A 1
C18A C 1.0917(9) 0.4861(7) 0.7171(9) 0.0634(19) Uani 0.391(12) 1 d G U P A 1
H18A H 1.134509 0.562647 0.720205 0.076 Uiso 0.391(12) 1 calc R U P A 1
C17A C 1.0506(9) 0.4420(9) 0.8158(6) 0.064(2) Uani 0.391(12) 1 d G U P A 1
H17A H 1.065328 0.488353 0.886414 0.077 Uiso 0.391(12) 1 calc R U P A 1
C16A C 0.9880(9) 0.3300(10) 0.8112(6) 0.0677(19) Uani 0.391(12) 1 d G U P A 1
H16A H 0.959880 0.299804 0.878691 0.081 Uiso 0.391(12) 1 calc R U P A 1
C15A C 0.9664(11) 0.2621(8) 0.7079(9) 0.0674(18) Uani 0.391(12) 1 d G U P A 1
H15A H 0.923612 0.185546 0.704758 0.081 Uiso 0.391(12) 1 calc R U P A 1
C12B C 0.9493(9) 0.1684(8) 0.4319(7) 0.0556(16) Uani 0.609(12) 1 d D U P A 2
H12B H 0.916934 0.113622 0.482235 0.067 Uiso 0.609(12) 1 calc R U P A 2
C13B C 1.0052(7) 0.2726(6) 0.4772(6) 0.0523(13) Uani 0.609(12) 1 d D U P A 2
H13B H 1.041675 0.324086 0.426571 0.063 Uiso 0.609(12) 1 calc R U P A 2
C14B C 1.0144(9) 0.3141(6) 0.6024(3) 0.0577(13) Uani 0.609(12) 1 d G U P A 2
C19B C 1.0754(8) 0.4237(6) 0.6392(5) 0.0578(12) Uani 0.609(12) 1 d G U P A 2
H19B H 1.112613 0.471343 0.586094 0.069 Uiso 0.609(12) 1 calc R U P A 2
C18B C 1.0819(6) 0.4636(5) 0.7539(5) 0.0620(14) Uani 0.609(12) 1 d G U P A 2
H18B H 1.123574 0.538528 0.779095 0.074 Uiso 0.609(12) 1 calc R U P A 2
C17B C 1.0275(6) 0.3939(7) 0.8317(3) 0.0675(16) Uani 0.609(12) 1 d G U P A 2
H17B H 1.031906 0.421215 0.910018 0.081 Uiso 0.609(12) 1 calc R U P A 2
C16B C 0.9665(6) 0.2843(7) 0.7948(4) 0.0770(15) Uani 0.609(12) 1 d G U P A 2
H16B H 0.929274 0.236716 0.847942 0.092 Uiso 0.609(12) 1 calc R U P A 2
C15B C 0.9600(7) 0.2444(5) 0.6801(5) 0.0701(14) Uani 0.609(12) 1 d G U P A 2
H15B H 0.918311 0.169529 0.654941 0.084 Uiso 0.609(12) 1 calc R U P A 2
N2 N 0.5663(2) 0.2617(2) 0.14832(17) 0.0573(5) Uani 1 1 d . . . . .
C20 C 0.5831(3) 0.1807(2) 0.2303(2) 0.0622(7) Uani 1 1 d . . . . .
H20 H 0.572750 0.097165 0.207967 0.075 Uiso 1 1 calc R U . . .
C21 C 0.6144(3) 0.2115(2) 0.3450(2) 0.0621(7) Uani 1 1 d . . . . .
H21 H 0.626699 0.149803 0.399357 0.075 Uiso 1 1 calc R U . . .
C22 C 0.6282(2) 0.3318(2) 0.3820(2) 0.0540(6) Uani 1 1 d . . . . .
C23 C 0.6103(2) 0.4163(2) 0.2959(2) 0.0607(6) Uani 1 1 d . . . . .
H23 H 0.619152 0.500464 0.315726 0.073 Uiso 1 1 calc R U . . .
C24 C 0.5801(3) 0.3781(3) 0.1835(2) 0.0628(7) Uani 1 1 d . . . . .
H24 H 0.568278 0.437707 0.126965 0.075 Uiso 1 1 calc R U . . .
C25A C 0.651(2) 0.389(2) 0.4886(16) 0.059(3) Uani 0.35(3) 1 d D U P B 1
C26A C 0.6772(17) 0.432(2) 0.5794(14) 0.059(3) Uani 0.35(3) 1 d D U P B 1
C25B C 0.6607(11) 0.3570(8) 0.5102(8) 0.0490(15) Uani 0.65(3) 1 d D U P B 2
H25B H 0.677224 0.290870 0.558923 0.059 Uiso 0.65(3) 1 calc R U P B 2
C26B C 0.6671(9) 0.4710(8) 0.5580(8) 0.0523(15) Uani 0.65(3) 1 d D U P B 2
H26B H 0.654329 0.536718 0.508119 0.063 Uiso 0.65(3) 1 calc R U P B 2
C27 C 0.6932(2) 0.4989(2) 0.6859(2) 0.0593(6) Uani 1 1 d . . . . .
C28 C 0.6916(3) 0.4204(3) 0.7750(3) 0.0712(8) Uani 1 1 d . . . . .
H28 H 0.678145 0.336008 0.757981 0.085 Uiso 1 1 calc R U . . .
C29 C 0.7093(3) 0.4627(3) 0.8876(3) 0.0819(9) Uani 1 1 d . . . . .
H29 H 0.707680 0.407515 0.947875 0.098 Uiso 1 1 calc R U . . .
C30 C 0.7293(3) 0.5844(4) 0.9137(3) 0.0846(10) Uani 1 1 d . . . . .
H30 H 0.741181 0.613414 0.991889 0.102 Uiso 1 1 calc R U . . .
C31 C 0.7322(3) 0.6642(3) 0.8266(3) 0.0787(9) Uani 1 1 d . . . . .
H31 H 0.746885 0.748361 0.844469 0.094 Uiso 1 1 calc R U . . .
C32 C 0.7138(3) 0.6222(3) 0.7133(3) 0.0681(7) Uani 1 1 d . . . . .
H32 H 0.715053 0.677795 0.653260 0.082 Uiso 1 1 calc R U . . .


_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 1.896(2) . ?
Br2 C3 1.895(2) . ?
O1 H1 0.8400 . ?
O1 C6 1.345(3) . ?
O2 H2 0.8400 . ?
O2 C4 1.347(3) . ?
N1 C7 1.319(4) . ?
N1 C11 1.326(4) . ?
C1 C2 1.378(3) . ?
C1 C6 1.393(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.383(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(4) . ?
C9 C10 1.377(4) . ?
C9 C12A 1.425(15) . ?
C9 C12B 1.491(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9500 . ?
C12A C13A 1.14(2) . ?
C13A C14A 1.381(12) . ?
C14A C19A 1.3900 . ?
C14A C15A 1.3900 . ?
C19A H19A 0.9500 . ?
C19A C18A 1.3900 . ?
C18A H18A 0.9500 . ?
C18A C17A 1.3900 . ?
C17A H17A 0.9500 . ?
C17A C16A 1.3900 . ?
C16A H16A 0.9500 . ?
C16A C15A 1.3900 . ?
C15A H15A 0.9500 . ?
C12B H12B 0.9500 . ?
C12B C13B 1.345(12) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.509(7) . ?
C14B C19B 1.3900 . ?
C14B C15B 1.3900 . ?
C19B H19B 0.9500 . ?
C19B C18B 1.3900 . ?
C18B H18B 0.9500 . ?
C18B C17B 1.3900 . ?
C17B H17B 0.9500 . ?
C17B C16B 1.3900 . ?
C16B H16B 0.9500 . ?
C16B C15B 1.3900 . ?
C15B H15B 0.9500 . ?
N2 C20 1.334(3) . ?
N2 C24 1.335(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.370(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(3) . ?
C22 C23 1.397(4) . ?
C22 C25A 1.369(16) . ?
C22 C25B 1.510(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.363(4) . ?
C24 H24 0.9500 . ?
C25A C26A 1.14(2) . ?
C26A C27 1.417(15) . ?
C25B H25B 0.9500 . ?
C25B C26B 1.356(13) . ?
C26B H26B 0.9500 . ?
C26B C27 1.506(9) . ?
C27 C28 1.381(4) . ?
C27 C32 1.393(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.371(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.373(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.374(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.377(4) . ?
C32 H32 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
C6 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 116.3(2) . . ?
C2 C1 Br1 119.46(16) . . ?
C2 C1 C6 121.2(2) . . ?
C6 C1 Br1 119.35(17) . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 Br2 119.53(16) . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 Br2 119.61(17) . . ?
O2 C4 C3 119.0(2) . . ?
O2 C4 C5 122.6(2) . . ?
C3 C4 C5 118.4(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
O1 C6 C1 118.9(2) . . ?
O1 C6 C5 123.2(2) . . ?
C5 C6 C1 117.9(2) . . ?
N1 C7 H7 118.3 . . ?
N1 C7 C8 123.4(3) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 116.4(2) . . ?
C8 C9 C12A 131.4(6) . . ?
C8 C9 C12B 114.2(4) . . ?
C10 C9 C12A 112.2(6) . . ?
C10 C9 C12B 129.3(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
N1 C11 C10 124.1(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C13A C12A C9 173.0(18) . . ?
C12A C13A C14A 174.5(17) . . ?
C13A C14A C19A 118.9(7) . . ?
C13A C14A C15A 121.1(7) . . ?
C19A C14A C15A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C9 C12B H12B 118.4 . . ?
C13B C12B C9 123.1(8) . . ?
C13B C12B H12B 118.4 . . ?
C12B C13B H13B 117.5 . . ?
C12B C13B C14B 125.0(8) . . ?
C14B C13B H13B 117.5 . . ?
C19B C14B C13B 119.8(4) . . ?
C19B C14B C15B 120.0 . . ?
C15B C14B C13B 120.2(4) . . ?
C14B C19B H19B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C19B C18B C17B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C17B C16B C15B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C20 N2 C24 116.3(2) . . ?
N2 C20 H20 118.2 . . ?
N2 C20 C21 123.6(2) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 115.8(2) . . ?
C21 C22 C25B 116.6(4) . . ?
C23 C22 C25B 127.5(4) . . ?
C25A C22 C21 133.5(10) . . ?
C25A C22 C23 110.6(10) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
N2 C24 C23 123.7(3) . . ?
N2 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
C26A C25A C22 175(3) . . ?
C25A C26A C27 170(3) . . ?
C22 C25B H25B 118.9 . . ?
C26B C25B C22 122.1(11) . . ?
C26B C25B H25B 118.9 . . ?
C25B C26B H26B 118.2 . . ?
C25B C26B C27 123.5(12) . . ?
C27 C26B H26B 118.2 . . ?
C28 C27 C26A 109.3(11) . . ?
C28 C27 C26B 128.5(4) . . ?
C28 C27 C32 118.3(3) . . ?
C32 C27 C26A 132.3(11) . . ?
C32 C27 C26B 113.0(4) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.3(3) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 H32 119.7 . . ?
C31 C32 C27 120.6(3) . . ?
C31 C32 H32 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.85 2.689(3) 175.5 . yes
O2 H2 N2 0.84 1.86 2.696(3) 172.1 . yes

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
Br1 C1 C2 C3 178.37(16) . . . . ?
Br1 C1 C6 O1 2.2(3) . . . . ?
Br1 C1 C6 C5 -177.10(18) . . . . ?
Br2 C3 C4 O2 2.7(3) . . . . ?
Br2 C3 C4 C5 -177.70(18) . . . . ?
O2 C4 C5 C6 -179.6(2) . . . . ?
N1 C7 C8 C9 0.9(5) . . . . ?
C1 C2 C3 Br2 177.53(16) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C6 O1 -178.9(2) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C3 C4 O2 -179.1(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 O1 178.8(2) . . . . ?
C4 C5 C6 C1 -1.9(4) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 N1 C11 C10 -2.6(4) . . . . ?
C7 C8 C9 C10 -2.4(4) . . . . ?
C7 C8 C9 C12A 177.0(10) . . . . ?
C7 C8 C9 C12B 175.7(5) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C8 C9 C12B C13B -177.4(8) . . . . ?
C9 C10 C11 N1 1.0(5) . . . . ?
C9 C12B C13B C14B 176.2(7) . . . . ?
C10 C9 C12B C13B 0.3(13) . . . . ?
C11 N1 C7 C8 1.7(4) . . . . ?
C12A C9 C10 C11 -178.0(8) . . . . ?
C13A C14A C19A C18A 179.2(13) . . . . ?
C13A C14A C15A C16A -179.2(14) . . . . ?
C14A C19A C18A C17A 0.0 . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?
C19A C18A C17A C16A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C17A C16A C15A C14A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C12B C9 C10 C11 -176.2(6) . . . . ?
C12B C13B C14B C19B 179.6(8) . . . . ?
C12B C13B C14B C15B -1.8(12) . . . . ?
C13B C14B C19B C18B 178.6(8) . . . . ?
C13B C14B C15B C16B -178.6(8) . . . . ?
C14B C19B C18B C17B 0.0 . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C19B C18B C17B C16B 0.0 . . . . ?
C18B C17B C16B C15B 0.0 . . . . ?
C17B C16B C15B C14B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
N2 C20 C21 C22 1.2(4) . . . . ?
C20 N2 C24 C23 0.3(4) . . . . ?
C20 C21 C22 C23 -1.0(4) . . . . ?
C20 C21 C22 C25A 175.1(14) . . . . ?
C20 C21 C22 C25B 179.0(6) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C21 C22 C25B C26B -174.7(10) . . . . ?
C22 C23 C24 N2 -0.2(4) . . . . ?
C22 C25B C26B C27 177.0(6) . . . . ?
C23 C22 C25B C26B 5.3(15) . . . . ?
C24 N2 C20 C21 -0.8(4) . . . . ?
C25A C22 C23 C24 -176.5(11) . . . . ?
C25A C26A C27 C28 129(17) . . . . ?
C25A C26A C27 C32 -53(17) . . . . ?
C26A C27 C28 C29 177.9(9) . . . . ?
C26A C27 C32 C31 -176.9(11) . . . . ?
C25B C22 C23 C24 -179.5(6) . . . . ?
C25B C26B C27 C28 -13.4(14) . . . . ?
C25B C26B C27 C32 170.9(10) . . . . ?
C26B C27 C28 C29 -175.3(5) . . . . ?
C26B C27 C32 C31 176.4(5) . . . . ?
C27 C28 C29 C30 -0.2(5) . . . . ?
C28 C27 C32 C31 0.1(4) . . . . ?
C28 C29 C30 C31 -0.3(5) . . . . ?
C29 C30 C31 C32 0.7(5) . . . . ?
C30 C31 C32 C27 -0.6(4) . . . . ?
C32 C27 C28 C29 0.3(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_04_190
_database_code_depnum_ccdc_archive 'CCDC 2420443'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H11 N), C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H26 Br2 N2 O2'
_chemical_formula_weight         630.37
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.741(5)
_cell_length_b                   11.091(5)
_cell_length_c                   11.623(6)
_cell_angle_alpha                91.955(10)
_cell_angle_beta                 96.665(12)
_cell_angle_gamma                92.024(11)
_cell_volume                     1373.4(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9153
_cell_measurement_temperature    190.00
_cell_measurement_theta_max      26.420
_cell_measurement_theta_min      2.499
_shelx_estimated_absorpt_T_max   0.642
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.9014.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.163
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45706
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.444
_diffrn_ambient_temperature      190.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4459
_reflns_number_total             5557
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0127(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0224P)²+0.6477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0656
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72672(2) -0.04567(2) -0.40293(2) 0.03562(9) Uani 1 1 d . . . . .
Br2 Br 0.32331(2) 0.24403(2) -0.30816(2) 0.03817(10) Uani 1 1 d . . . . .
O1 O 0.80024(16) -0.00291(16) -0.14610(14) 0.0395(4) Uani 1 1 d . . . . .
H1 H 0.826500 0.018542 -0.077297 0.059 Uiso 1 1 calc R U . . .
O2 O 0.44823(16) 0.22864(17) -0.06317(15) 0.0442(5) Uani 1 1 d . . . . .
H2 H 0.491957 0.238822 0.001419 0.066 Uiso 1 1 calc R U . . .
N1 N 0.8852(2) 0.0590(2) 0.07540(17) 0.0402(5) Uani 1 1 d . . . . .
C1 C 0.6426(2) 0.0436(2) -0.29510(19) 0.0289(5) Uani 1 1 d . . . . .
C2 C 0.5330(2) 0.09893(19) -0.33345(19) 0.0291(5) Uani 1 1 d . . . . .
H2A H 0.501388 0.094083 -0.413330 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4697(2) 0.1614(2) -0.2549(2) 0.0293(5) Uani 1 1 d . . . . .
C4 C 0.5137(2) 0.1683(2) -0.1373(2) 0.0315(5) Uani 1 1 d . . . . .
C5 C 0.6245(2) 0.1118(2) -0.1008(2) 0.0331(5) Uani 1 1 d . . . . .
H5 H 0.655128 0.114995 -0.020640 0.040 Uiso 1 1 calc R U . . .
C6 C 0.6916(2) 0.0509(2) -0.1786(2) 0.0305(5) Uani 1 1 d . . . . .
C7 C 0.8488(3) -0.0076(3) 0.1588(2) 0.0468(7) Uani 1 1 d . . . . .
H7 H 0.804286 -0.082120 0.137565 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8721(3) 0.0257(2) 0.2752(2) 0.0477(7) Uani 1 1 d . . . . .
H8 H 0.844739 -0.026073 0.331506 0.057 Uiso 1 1 calc R U . . .
C9 C 0.9350(2) 0.1338(2) 0.3100(2) 0.0347(5) Uani 1 1 d . . . . .
C10 C 0.9761(2) 0.2021(2) 0.2229(2) 0.0395(6) Uani 1 1 d . . . . .
H10 H 1.021880 0.276404 0.241405 0.047 Uiso 1 1 calc R U . . .
C11 C 0.9500(3) 0.1611(3) 0.1099(2) 0.0469(7) Uani 1 1 d . . . . .
H11 H 0.980277 0.208840 0.051914 0.056 Uiso 1 1 calc R U . . .
C12 C 0.9521(2) 0.1716(2) 0.4330(2) 0.0397(6) Uani 1 1 d . . . . .
H12 H 0.921993 0.116244 0.484966 0.048 Uiso 1 1 calc R U . . .
C13 C 1.0048(2) 0.2739(2) 0.4799(2) 0.0351(6) Uani 1 1 d . . . . .
H13 H 1.040917 0.326957 0.429343 0.042 Uiso 1 1 calc R U . . .
C14 C 1.0128(2) 0.3136(2) 0.6024(2) 0.0337(5) Uani 1 1 d . . . . .
C15 C 0.9607(3) 0.2463(3) 0.6845(2) 0.0435(6) Uani 1 1 d . . . . .
H15 H 0.919525 0.170444 0.662468 0.052 Uiso 1 1 calc R U . . .
C16 C 0.9683(3) 0.2889(3) 0.7979(2) 0.0568(8) Uani 1 1 d . . . . .
H16 H 0.931890 0.241958 0.853085 0.068 Uiso 1 1 calc R U . . .
C17 C 1.0273(3) 0.3975(3) 0.8326(3) 0.0553(8) Uani 1 1 d . . . . .
H17 H 1.031361 0.425898 0.911061 0.066 Uiso 1 1 calc R U . . .
C18 C 1.0808(3) 0.4653(3) 0.7530(3) 0.0520(8) Uani 1 1 d . . . . .
H18 H 1.122945 0.540322 0.776614 0.062 Uiso 1 1 calc R U . . .
C19 C 1.0732(2) 0.4241(2) 0.6379(2) 0.0412(6) Uani 1 1 d . . . . .
H19 H 1.109562 0.471689 0.583133 0.049 Uiso 1 1 calc R U . . .
N2 N 0.57019(19) 0.26553(19) 0.15113(17) 0.0365(5) Uani 1 1 d . . . . .
C20 C 0.5848(2) 0.1824(2) 0.2310(2) 0.0407(6) Uani 1 1 d . . . . .
H20 H 0.573800 0.099854 0.206256 0.049 Uiso 1 1 calc R U . . .
C21 C 0.6150(2) 0.2095(2) 0.3477(2) 0.0396(6) Uani 1 1 d . . . . .
H21 H 0.624860 0.146421 0.400863 0.048 Uiso 1 1 calc R U . . .
C22 C 0.6311(2) 0.3296(2) 0.3878(2) 0.0330(5) Uani 1 1 d . . . . .
C23 C 0.6160(2) 0.4163(2) 0.3032(2) 0.0363(6) Uani 1 1 d . . . . .
H23 H 0.626162 0.499733 0.324935 0.044 Uiso 1 1 calc R U . . .
C24 C 0.5864(2) 0.3808(2) 0.1891(2) 0.0378(6) Uani 1 1 d . . . . .
H24 H 0.576832 0.441730 0.133590 0.045 Uiso 1 1 calc R U . . .
C25 C 0.6597(2) 0.3597(2) 0.5124(2) 0.0357(6) Uani 1 1 d . . . . .
H25 H 0.673353 0.294517 0.562699 0.043 Uiso 1 1 calc R U . . .
C26 C 0.6682(2) 0.4705(2) 0.5608(2) 0.0364(6) Uani 1 1 d . . . . .
H26 H 0.657966 0.535018 0.509185 0.044 Uiso 1 1 calc R U . . .
C27 C 0.6915(2) 0.5045(2) 0.6846(2) 0.0352(6) Uani 1 1 d . . . . .
C28 C 0.6887(2) 0.4211(2) 0.7715(2) 0.0404(6) Uani 1 1 d . . . . .
H28 H 0.675169 0.337568 0.751158 0.049 Uiso 1 1 calc R U . . .
C29 C 0.7055(3) 0.4590(3) 0.8871(2) 0.0489(7) Uani 1 1 d . . . . .
H29 H 0.703309 0.401375 0.945594 0.059 Uiso 1 1 calc R U . . .
C30 C 0.7255(3) 0.5799(3) 0.9180(3) 0.0526(8) Uani 1 1 d . . . . .
H30 H 0.736332 0.605358 0.997534 0.063 Uiso 1 1 calc R U . . .
C31 C 0.7297(3) 0.6639(3) 0.8336(3) 0.0522(8) Uani 1 1 d . . . . .
H31 H 0.744778 0.746990 0.855005 0.063 Uiso 1 1 calc R U . . .
C32 C 0.7119(2) 0.6269(2) 0.7178(2) 0.0442(7) Uani 1 1 d . . . . .
H32 H 0.713525 0.685266 0.659961 0.053 Uiso 1 1 calc R U . . .


_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 1.899(2) . ?
Br2 C3 1.900(2) . ?
O1 H1 0.8400 . ?
O1 C6 1.350(3) . ?
O2 H2 0.8400 . ?
O2 C4 1.348(3) . ?
N1 C7 1.326(3) . ?
N1 C11 1.333(4) . ?
C1 C2 1.382(3) . ?
C1 C6 1.393(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.383(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.394(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(4) . ?
C9 C10 1.388(3) . ?
C9 C12 1.465(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.369(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.321(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.468(3) . ?
C14 C15 1.388(4) . ?
C14 C19 1.393(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.366(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(4) . ?
C19 H19 0.9500 . ?
N2 C20 1.331(3) . ?
N2 C24 1.338(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.394(3) . ?
C22 C23 1.398(3) . ?
C22 C25 1.471(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.368(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.329(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.466(3) . ?
C27 C28 1.395(4) . ?
C27 C32 1.401(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.379(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.384(4) . ?
C32 H32 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
C6 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 116.0(2) . . ?
C2 C1 Br1 119.35(17) . . ?
C2 C1 C6 121.2(2) . . ?
C6 C1 Br1 119.49(18) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 Br2 119.75(17) . . ?
C2 C3 C4 121.1(2) . . ?
C4 C3 Br2 119.15(17) . . ?
O2 C4 C3 119.3(2) . . ?
O2 C4 C5 122.5(2) . . ?
C3 C4 C5 118.2(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.1 . . ?
O1 C6 C1 118.8(2) . . ?
O1 C6 C5 123.1(2) . . ?
C5 C6 C1 118.2(2) . . ?
N1 C7 H7 118.3 . . ?
N1 C7 C8 123.4(3) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 116.3(2) . . ?
C8 C9 C12 119.7(2) . . ?
C10 C9 C12 124.0(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.3 . . ?
N1 C11 C10 124.6(3) . . ?
N1 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
C9 C12 H12 116.3 . . ?
C13 C12 C9 127.3(2) . . ?
C13 C12 H12 116.3 . . ?
C12 C13 H13 116.8 . . ?
C12 C13 C14 126.4(2) . . ?
C14 C13 H13 116.8 . . ?
C15 C14 C13 122.6(2) . . ?
C15 C14 C19 118.3(2) . . ?
C19 C14 C13 119.1(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 N2 C24 116.6(2) . . ?
N2 C20 H20 118.2 . . ?
N2 C20 C21 123.6(2) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 116.0(2) . . ?
C21 C22 C25 120.5(2) . . ?
C23 C22 C25 123.5(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.0 . . ?
N2 C24 C23 123.9(2) . . ?
N2 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
C22 C25 H25 117.2 . . ?
C26 C25 C22 125.5(2) . . ?
C26 C25 H25 117.2 . . ?
C25 C26 H26 116.3 . . ?
C25 C26 C27 127.4(2) . . ?
C27 C26 H26 116.3 . . ?
C28 C27 C26 123.0(2) . . ?
C28 C27 C32 118.2(2) . . ?
C32 C27 C26 118.7(2) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.5(3) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 119.9(3) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 H32 119.6 . . ?
C31 C32 C27 120.9(3) . . ?
C31 C32 H32 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.85 2.687(3) 177.6 . yes
O2 H2 N2 0.84 1.85 2.688(3) 173.0 . yes

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
Br1 C1 C2 C3 178.36(16) . . . . ?
Br1 C1 C6 O1 2.0(3) . . . . ?
Br1 C1 C6 C5 -176.81(17) . . . . ?
Br2 C3 C4 O2 3.0(3) . . . . ?
Br2 C3 C4 C5 -176.98(18) . . . . ?
O2 C4 C5 C6 -179.3(2) . . . . ?
N1 C7 C8 C9 0.8(5) . . . . ?
C1 C2 C3 Br2 177.06(17) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C1 C6 O1 -178.8(2) . . . . ?
C2 C1 C6 C5 2.4(3) . . . . ?
C2 C3 C4 O2 -179.1(2) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 O1 178.9(2) . . . . ?
C4 C5 C6 C1 -2.4(4) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C7 N1 C11 C10 -2.6(4) . . . . ?
C7 C8 C9 C10 -2.4(4) . . . . ?
C7 C8 C9 C12 176.1(3) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C8 C9 C12 C13 -176.8(3) . . . . ?
C9 C10 C11 N1 0.9(4) . . . . ?
C9 C12 C13 C14 175.3(2) . . . . ?
C10 C9 C12 C13 1.7(4) . . . . ?
C11 N1 C7 C8 1.7(4) . . . . ?
C12 C9 C10 C11 -176.9(3) . . . . ?
C12 C13 C14 C15 -1.9(4) . . . . ?
C12 C13 C14 C19 179.2(3) . . . . ?
C13 C14 C15 C16 -178.5(3) . . . . ?
C13 C14 C19 C18 179.0(2) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C14 C19 C18 0.0(4) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C17 C18 C19 C14 -0.7(4) . . . . ?
C19 C14 C15 C16 0.4(4) . . . . ?
N2 C20 C21 C22 0.4(4) . . . . ?
C20 N2 C24 C23 -0.3(4) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C20 C21 C22 C25 178.2(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C21 C22 C25 C26 -175.0(3) . . . . ?
C22 C23 C24 N2 0.1(4) . . . . ?
C22 C25 C26 C27 177.4(2) . . . . ?
C23 C22 C25 C26 3.7(4) . . . . ?
C24 N2 C20 C21 0.0(4) . . . . ?
C25 C22 C23 C24 -178.4(2) . . . . ?
C25 C26 C27 C28 -10.5(4) . . . . ?
C25 C26 C27 C32 172.5(3) . . . . ?
C26 C27 C28 C29 -176.9(2) . . . . ?
C26 C27 C32 C31 177.6(2) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C28 C27 C32 C31 0.5(4) . . . . ?
C28 C29 C30 C31 -0.5(4) . . . . ?
C29 C30 C31 C32 1.0(4) . . . . ?
C30 C31 C32 C27 -1.0(4) . . . . ?
C32 C27 C28 C29 0.1(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'

# 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_gro23_05_290
_database_code_depnum_ccdc_archive 'CCDC 2420444'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_gro23_05_290        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note  
RESPONSE: Due to slight disorder about the C6H4Br2O2 molecule in the 
          structure.
;
_vrf_PLAT906_gro23_05_290        
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.170 Check 
RESPONSE: Due to slight differences in the strongest reflections at this 
          temperature.
;
_vrf_PLAT911_gro23_05_290        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
_vrf_PLAT913_gro23_05_290        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          4 Note  
RESPONSE: These reflections were affected by a slightly misaligned beamstop
          mask. 
;
_vrf_PLAT250_gro23_05_270        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note  
RESPONSE: Due to slight disorder about the C6H4Br2O2 molecule in the 
          structure.
;
_vrf_PLAT911_gro23_05_270        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
_vrf_PLAT913_gro23_05_270        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          4 Note  
RESPONSE: These reflections were affected by a slightly misaligned beamstop
          mask. 
;
_vrf_PLAT250_gro23_05_250        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note  
RESPONSE: Due to slight disorder about the C6H4Br2O2 molecule in the 
          structure.
;
_vrf_PLAT911_gro23_05_250        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
_vrf_PLAT913_gro23_05_250        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          4 Note  
RESPONSE: These reflections were affected by a slightly misaligned beamstop
          mask. 
;
_vrf_PLAT250_gro23_05_230        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note  
RESPONSE: Due to slight disorder about the C6H4Br2O2 molecule in the 
          structure.
;
_vrf_PLAT911_gro23_05_230        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
_vrf_PLAT913_gro23_05_230        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          4 Note  
RESPONSE: These reflections were affected by a slightly misaligned beamstop
          mask. 
;
_vrf_PLAT250_gro23_05_210        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note  
RESPONSE: Due to slight disorder about the C6H4Br2O2 molecule in the 
          structure.
;
_vrf_PLAT911_gro23_05_210        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
_vrf_PLAT913_gro23_05_210        
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          4 Note  
RESPONSE: These reflections were affected by a slightly misaligned beamstop
          mask. 
;
_vrf_PLAT250_gro23_05_190        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note  
RESPONSE: Due to slight disorder about the C6H4Br2O2 molecule in the 
          structure.
;
_vrf_PLAT911_gro23_05_190        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2023-04-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
ryangroeneman19@webster.edu
daniel-unruh@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H9 N), C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H22 Br2 N2 O2'
_chemical_formula_weight         626.33
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7221(13)
_cell_length_b                   19.6785(19)
_cell_length_c                   10.7022(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.145(2)
_cell_angle_gamma                90
_cell_volume                     2825.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7887
_cell_measurement_temperature    290.00
_cell_measurement_theta_max      23.526
_cell_measurement_theta_min      2.433
_shelx_estimated_absorpt_T_max   0.692
_shelx_estimated_absorpt_T_min   0.675
_exptl_absorpt_coefficient_mu    2.900
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0645 before and 0.0455 after correction.
The Ratio of minimum to maximum transmission is 0.8894.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.137
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45582
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_min         2.070
_diffrn_ambient_temperature      290.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3492
_reflns_number_total             5357
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0150P)²+1.8668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0737
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.86797(3) 0.48718(2) 0.39954(4) 0.08982(15) Uani 1 1 d . . . . .
Br2 Br 0.63510(3) 0.30948(2) 0.04396(3) 0.09618(17) Uani 1 1 d . . . . .
O1 O 0.70807(16) 0.45643(12) 0.5477(2) 0.0767(6) Uani 1 1 d . . . . .
H1 H 0.667728 0.444758 0.590239 0.115 Uiso 1 1 calc R U . . .
O2 O 0.51145(16) 0.30391(13) 0.2461(2) 0.0778(6) Uani 1 1 d . . . . .
H2 H 0.474209 0.307022 0.296523 0.117 Uiso 1 1 calc R U . . .
C1 C 0.7550(2) 0.43033(15) 0.3526(3) 0.0567(8) Uani 1 1 d . . . . .
C2 C 0.73845(19) 0.39685(15) 0.2380(3) 0.0585(8) Uani 1 1 d . . . . .
H2A H 0.782292 0.402636 0.183313 0.070 Uiso 1 1 calc R U . . .
C3 C 0.6573(2) 0.35465(16) 0.2032(3) 0.0567(8) Uani 1 1 d . . . . .
C4 C 0.5913(2) 0.34520(16) 0.2842(3) 0.0553(7) Uani 1 1 d . . . . .
C5 C 0.6093(2) 0.37914(15) 0.3994(3) 0.0567(8) Uani 1 1 d . . . . .
H5 H 0.565816 0.373003 0.454483 0.068 Uiso 1 1 calc R U . . .
C6 C 0.6900(2) 0.42203(15) 0.4355(3) 0.0551(7) Uani 1 1 d . . . . .
N1 N 0.57112(19) 0.43315(16) 0.6970(2) 0.0695(7) Uani 1 1 d . . . . .
C7 C 0.5162(3) 0.3783(2) 0.7031(3) 0.0805(10) Uani 1 1 d . . . . .
H7 H 0.530833 0.339080 0.662234 0.097 Uiso 1 1 calc R U . . .
C8 C 0.4388(2) 0.37607(18) 0.7666(3) 0.0743(10) Uani 1 1 d . . . . .
H8 H 0.401474 0.336579 0.766386 0.089 Uiso 1 1 calc R U . . .
C9 C 0.4172(2) 0.43319(17) 0.8306(3) 0.0595(8) Uani 1 1 d . . . . .
C10 C 0.4758(2) 0.48971(17) 0.8286(3) 0.0708(9) Uani 1 1 d . . . . .
H10 H 0.465396 0.528879 0.872639 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5505(2) 0.48724(18) 0.7602(3) 0.0737(9) Uani 1 1 d . . . . .
H11 H 0.588715 0.526087 0.758291 0.088 Uiso 1 1 calc R U . . .
C12 C 0.3371(2) 0.43410(17) 0.8990(3) 0.0695(9) Uani 1 1 d . . . . .
C13 C 0.2703(2) 0.43560(16) 0.9532(3) 0.0643(8) Uani 1 1 d . . . . .
C14 C 0.1878(2) 0.43557(16) 1.0174(3) 0.0575(8) Uani 1 1 d . . . . .
C15 C 0.1170(2) 0.38522(17) 0.9923(3) 0.0666(8) Uani 1 1 d . . . . .
H15 H 0.122060 0.351537 0.933005 0.080 Uiso 1 1 calc R U . . .
C16 C 0.0388(2) 0.38424(19) 1.0538(3) 0.0771(10) Uani 1 1 d . . . . .
H16 H -0.008779 0.349954 1.036106 0.092 Uiso 1 1 calc R U . . .
C17 C 0.0306(2) 0.4331(2) 1.1406(3) 0.0821(11) Uani 1 1 d . . . . .
H17 H -0.022535 0.432287 1.182115 0.099 Uiso 1 1 calc R U . . .
C18 C 0.1001(3) 0.4834(2) 1.1668(4) 0.0886(11) Uani 1 1 d . . . . .
H18 H 0.094376 0.516668 1.226619 0.106 Uiso 1 1 calc R U . . .
C19 C 0.1787(2) 0.48530(17) 1.1055(3) 0.0776(10) Uani 1 1 d . . . . .
H19 H 0.225663 0.519973 1.123207 0.093 Uiso 1 1 calc R U . . .
N2 N 0.37272(19) 0.30609(16) 0.3951(3) 0.0729(8) Uani 1 1 d . . . . .
C20 C 0.3641(2) 0.25802(19) 0.4793(3) 0.0703(9) Uani 1 1 d . . . . .
H20 H 0.411378 0.223434 0.493030 0.084 Uiso 1 1 calc R U . . .
C21 C 0.2896(2) 0.25639(17) 0.5471(3) 0.0635(8) Uani 1 1 d . . . . .
H21 H 0.286725 0.221212 0.604252 0.076 Uiso 1 1 calc R U . . .
C22 C 0.2189(2) 0.30747(16) 0.5297(3) 0.0583(8) Uani 1 1 d . . . . .
C23 C 0.2275(2) 0.35828(17) 0.4430(3) 0.0764(10) Uani 1 1 d . . . . .
H23 H 0.182304 0.394098 0.428620 0.092 Uiso 1 1 calc R U . . .
C24 C 0.3037(3) 0.35469(19) 0.3791(3) 0.0840(11) Uani 1 1 d . . . . .
H24 H 0.307705 0.388709 0.320095 0.101 Uiso 1 1 calc R U . . .
C25 C 0.1385(2) 0.30609(16) 0.5964(3) 0.0650(8) Uani 1 1 d . . . . .
C26 C 0.0697(2) 0.30154(16) 0.6474(3) 0.0622(8) Uani 1 1 d . . . . .
C27 C -0.0134(2) 0.29319(16) 0.7080(3) 0.0553(7) Uani 1 1 d . . . . .
C28 C -0.0146(2) 0.23849(17) 0.7894(3) 0.0668(8) Uani 1 1 d . . . . .
H28 H 0.038176 0.207862 0.803928 0.080 Uiso 1 1 calc R U . . .
C29 C -0.0933(3) 0.2292(2) 0.8487(3) 0.0823(11) Uani 1 1 d . . . . .
H29 H -0.093330 0.192767 0.903915 0.099 Uiso 1 1 calc R U . . .
C30 C -0.1712(3) 0.2736(3) 0.8263(4) 0.0940(13) Uani 1 1 d . . . . .
H30 H -0.224688 0.267114 0.865936 0.113 Uiso 1 1 calc R U . . .
C31 C -0.1713(3) 0.3277(2) 0.7458(4) 0.0924(12) Uani 1 1 d . . . . .
H31 H -0.224520 0.357987 0.731834 0.111 Uiso 1 1 calc R U . . .
C32 C -0.0934(2) 0.33755(17) 0.6856(3) 0.0732(9) Uani 1 1 d . . . . .
H32 H -0.094349 0.373964 0.629985 0.088 Uiso 1 1 calc R U . . .


_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 1.892(3) . ?
Br2 C3 1.889(3) . ?
O1 H1 0.8200 . ?
O1 C6 1.355(3) . ?
O2 H2 0.8200 . ?
O2 C4 1.356(3) . ?
C1 C2 1.369(4) . ?
C1 C6 1.392(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.376(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
N1 C7 1.326(4) . ?
N1 C11 1.323(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(4) . ?
C9 C10 1.376(4) . ?
C9 C12 1.443(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.184(4) . ?
C13 C14 1.443(4) . ?
C14 C15 1.374(4) . ?
C14 C19 1.382(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.358(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.362(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(5) . ?
C19 H19 0.9300 . ?
N2 C20 1.328(4) . ?
N2 C24 1.331(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(4) . ?
C22 C23 1.386(4) . ?
C22 C25 1.435(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.367(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.189(4) . ?
C26 C27 1.436(4) . ?
C27 C28 1.387(4) . ?
C27 C32 1.383(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.375(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.362(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.369(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.374(5) . ?
C32 H32 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
C6 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C2 C1 Br1 119.6(2) . . ?
C2 C1 C6 120.4(3) . . ?
C6 C1 Br1 119.9(2) . . ?
C1 C2 H2A 119.8 . . ?
C1 C2 C3 120.3(2) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 Br2 119.7(2) . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 Br2 119.8(2) . . ?
O2 C4 C3 118.9(3) . . ?
O2 C4 C5 122.7(2) . . ?
C5 C4 C3 118.4(3) . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
O1 C6 C1 118.9(3) . . ?
O1 C6 C5 122.6(2) . . ?
C5 C6 C1 118.5(3) . . ?
C11 N1 C7 116.4(3) . . ?
N1 C7 H7 118.1 . . ?
N1 C7 C8 123.8(3) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C12 121.8(3) . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 C12 120.6(3) . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
N1 C11 C10 124.2(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C13 C12 C9 178.7(4) . . ?
C12 C13 C14 178.3(4) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 C19 118.9(3) . . ?
C19 C14 C13 121.1(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C20 N2 C24 115.9(3) . . ?
N2 C20 H20 118.1 . . ?
N2 C20 C21 123.9(3) . . ?
C21 C20 H20 118.1 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C23 117.3(3) . . ?
C21 C22 C25 120.7(3) . . ?
C23 C22 C25 121.9(3) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 C22 118.6(3) . . ?
C24 C23 H23 120.7 . . ?
N2 C24 C23 124.8(3) . . ?
N2 C24 H24 117.6 . . ?
C23 C24 H24 117.6 . . ?
C26 C25 C22 176.0(3) . . ?
C25 C26 C27 177.7(3) . . ?
C28 C27 C26 119.2(3) . . ?
C32 C27 C26 121.8(3) . . ?
C32 C27 C28 119.0(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.9(4) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.5(4) . . ?
C32 C31 H31 119.8 . . ?
C27 C32 H32 120.1 . . ?
C31 C32 C27 119.8(3) . . ?
C31 C32 H32 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.94 2.749(3) 170.4 . yes
O2 H2 N2 0.82 1.92 2.729(3) 171.0 . yes

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
Br1 C1 C2 C3 179.2(2) . . . . ?
Br1 C1 C6 O1 1.5(4) . . . . ?
Br1 C1 C6 C5 -178.8(2) . . . . ?
Br2 C3 C4 O2 -0.6(4) . . . . ?
Br2 C3 C4 C5 -179.7(2) . . . . ?
O2 C4 C5 C6 -178.7(3) . . . . ?
C1 C2 C3 Br2 179.5(2) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C1 C6 O1 -179.4(3) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C2 C3 C4 O2 179.2(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 O1 179.2(3) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
N1 C7 C8 C9 -1.5(5) . . . . ?
C7 N1 C11 C10 -1.0(5) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C7 C8 C9 C12 -179.9(3) . . . . ?
C8 C9 C10 C11 2.0(5) . . . . ?
C9 C10 C11 N1 -1.2(5) . . . . ?
C11 N1 C7 C8 2.4(5) . . . . ?
C12 C9 C10 C11 -178.8(3) . . . . ?
C13 C14 C15 C16 179.3(3) . . . . ?
C13 C14 C19 C18 -179.0(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C14 C19 C18 0.5(5) . . . . ?
C15 C16 C17 C18 0.0(6) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C17 C18 C19 C14 -0.6(6) . . . . ?
C19 C14 C15 C16 -0.2(5) . . . . ?
N2 C20 C21 C22 -0.7(5) . . . . ?
C20 N2 C24 C23 0.6(5) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C20 C21 C22 C25 178.1(3) . . . . ?
C21 C22 C23 C24 0.8(5) . . . . ?
C22 C23 C24 N2 -1.2(6) . . . . ?
C24 N2 C20 C21 0.3(5) . . . . ?
C25 C22 C23 C24 -177.3(3) . . . . ?
C26 C27 C28 C29 -180.0(3) . . . . ?
C26 C27 C32 C31 -179.9(3) . . . . ?
C27 C28 C29 C30 0.8(5) . . . . ?
C28 C27 C32 C31 1.3(5) . . . . ?
C28 C29 C30 C31 -0.5(6) . . . . ?
C29 C30 C31 C32 0.7(6) . . . . ?
C30 C31 C32 C27 -1.1(5) . . . . ?
C32 C27 C28 C29 -1.2(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_05_270
_database_code_depnum_ccdc_archive 'CCDC 2420445'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-04-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H9 N), C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H22 Br2 N2 O2'
_chemical_formula_weight         626.33
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7170(12)
_cell_length_b                   19.6387(18)
_cell_length_c                   10.6868(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.276(2)
_cell_angle_gamma                90
_cell_volume                     2813.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7609
_cell_measurement_temperature    270.00
_cell_measurement_theta_max      23.542
_cell_measurement_theta_min      2.435
_shelx_estimated_absorpt_T_max   0.691
_shelx_estimated_absorpt_T_min   0.674
_exptl_absorpt_coefficient_mu    2.913
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0679 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.8796.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.137
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45254
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         2.074
_diffrn_ambient_temperature      270.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3611
_reflns_number_total             5338
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²+1.6604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0717
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.86793(2) 0.48738(2) 0.39934(4) 0.08169(14) Uani 1 1 d . . . . .
Br2 Br 0.63427(2) 0.30921(2) 0.04301(3) 0.08751(15) Uani 1 1 d . . . . .
O1 O 0.70799(15) 0.45671(12) 0.54773(19) 0.0699(6) Uani 1 1 d . . . . .
H1 H 0.668301 0.444560 0.590854 0.105 Uiso 1 1 calc R U . . .
O2 O 0.51048(15) 0.30389(12) 0.24552(19) 0.0708(6) Uani 1 1 d . . . . .
H2 H 0.474392 0.306089 0.297499 0.106 Uiso 1 1 calc R U . . .
C1 C 0.75437(19) 0.43052(14) 0.3524(3) 0.0515(7) Uani 1 1 d . . . . .
C2 C 0.73786(18) 0.39687(14) 0.2373(2) 0.0529(7) Uani 1 1 d . . . . .
H2A H 0.781720 0.402637 0.182636 0.064 Uiso 1 1 calc R U . . .
C3 C 0.65643(19) 0.35457(15) 0.2023(2) 0.0514(7) Uani 1 1 d . . . . .
C4 C 0.59062(19) 0.34516(14) 0.2835(2) 0.0493(7) Uani 1 1 d . . . . .
C5 C 0.60890(19) 0.37918(14) 0.3990(2) 0.0511(7) Uani 1 1 d . . . . .
H5 H 0.565584 0.372922 0.454153 0.061 Uiso 1 1 calc R U . . .
C6 C 0.68968(19) 0.42234(14) 0.4354(2) 0.0498(7) Uani 1 1 d . . . . .
N1 N 0.57140(18) 0.43292(15) 0.6975(2) 0.0631(7) Uani 1 1 d . . . . .
C7 C 0.5156(2) 0.37798(18) 0.7027(3) 0.0719(9) Uani 1 1 d . . . . .
H7 H 0.529676 0.338795 0.661014 0.086 Uiso 1 1 calc R U . . .
C8 C 0.4382(2) 0.37574(17) 0.7661(3) 0.0684(9) Uani 1 1 d . . . . .
H8 H 0.400669 0.336249 0.765668 0.082 Uiso 1 1 calc R U . . .
C9 C 0.41708(19) 0.43301(16) 0.8305(3) 0.0544(7) Uani 1 1 d . . . . .
C10 C 0.4759(2) 0.48976(16) 0.8293(3) 0.0641(8) Uani 1 1 d . . . . .
H10 H 0.465427 0.528935 0.873544 0.077 Uiso 1 1 calc R U . . .
C11 C 0.5509(2) 0.48725(17) 0.7608(3) 0.0673(9) Uani 1 1 d . . . . .
H11 H 0.589317 0.526125 0.759124 0.081 Uiso 1 1 calc R U . . .
C12 C 0.3368(2) 0.43399(16) 0.8988(3) 0.0624(8) Uani 1 1 d . . . . .
C13 C 0.2699(2) 0.43561(16) 0.9531(3) 0.0589(8) Uani 1 1 d . . . . .
C14 C 0.18763(19) 0.43562(15) 1.0169(3) 0.0518(7) Uani 1 1 d . . . . .
C15 C 0.1169(2) 0.38484(16) 0.9917(3) 0.0601(8) Uani 1 1 d . . . . .
H15 H 0.122205 0.350972 0.932696 0.072 Uiso 1 1 calc R U . . .
C16 C 0.0382(2) 0.38388(17) 1.0532(3) 0.0697(9) Uani 1 1 d . . . . .
H16 H -0.009385 0.349501 1.035320 0.084 Uiso 1 1 calc R U . . .
C17 C 0.0298(2) 0.43306(19) 1.1401(3) 0.0741(10) Uani 1 1 d . . . . .
H17 H -0.023223 0.432120 1.181756 0.089 Uiso 1 1 calc R U . . .
C18 C 0.0992(3) 0.48370(19) 1.1662(3) 0.0799(10) Uani 1 1 d . . . . .
H18 H 0.093302 0.517201 1.225585 0.096 Uiso 1 1 calc R U . . .
C19 C 0.1781(2) 0.48557(17) 1.1049(3) 0.0705(9) Uani 1 1 d . . . . .
H19 H 0.224981 0.520390 1.122797 0.085 Uiso 1 1 calc R U . . .
N2 N 0.37187(18) 0.30630(15) 0.3943(2) 0.0658(7) Uani 1 1 d . . . . .
C20 C 0.3638(2) 0.25795(17) 0.4788(3) 0.0625(8) Uani 1 1 d . . . . .
H20 H 0.411276 0.223400 0.492886 0.075 Uiso 1 1 calc R U . . .
C21 C 0.2890(2) 0.25644(16) 0.5465(3) 0.0592(8) Uani 1 1 d . . . . .
H21 H 0.286212 0.221183 0.603717 0.071 Uiso 1 1 calc R U . . .
C22 C 0.21791(19) 0.30764(15) 0.5291(3) 0.0526(7) Uani 1 1 d . . . . .
C23 C 0.2266(2) 0.35835(16) 0.4419(3) 0.0692(9) Uani 1 1 d . . . . .
H23 H 0.181036 0.394049 0.426937 0.083 Uiso 1 1 calc R U . . .
C24 C 0.3030(3) 0.35516(18) 0.3783(3) 0.0763(10) Uani 1 1 d . . . . .
H24 H 0.307215 0.389488 0.319708 0.092 Uiso 1 1 calc R U . . .
C25 C 0.1376(2) 0.30621(15) 0.5955(3) 0.0590(8) Uani 1 1 d . . . . .
C26 C 0.0690(2) 0.30173(15) 0.6467(3) 0.0558(7) Uani 1 1 d . . . . .
C27 C -0.01433(19) 0.29305(15) 0.7073(2) 0.0503(7) Uani 1 1 d . . . . .
C28 C -0.0148(2) 0.23824(16) 0.7887(3) 0.0604(8) Uani 1 1 d . . . . .
H28 H 0.038209 0.207693 0.803088 0.072 Uiso 1 1 calc R U . . .
C29 C -0.0933(3) 0.22873(19) 0.8484(3) 0.0751(10) Uani 1 1 d . . . . .
H29 H -0.092820 0.192182 0.903864 0.090 Uiso 1 1 calc R U . . .
C30 C -0.1720(3) 0.2730(2) 0.8261(3) 0.0853(12) Uani 1 1 d . . . . .
H30 H -0.225416 0.266279 0.865703 0.102 Uiso 1 1 calc R U . . .
C31 C -0.1723(2) 0.3274(2) 0.7456(4) 0.0840(11) Uani 1 1 d . . . . .
H31 H -0.225845 0.357537 0.731497 0.101 Uiso 1 1 calc R U . . .
C32 C -0.0944(2) 0.33780(16) 0.6854(3) 0.0667(8) Uani 1 1 d . . . . .
H32 H -0.095300 0.374600 0.630361 0.080 Uiso 1 1 calc R U . . .


_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 1.895(3) . ?
Br2 C3 1.888(3) . ?
O1 H1 0.8200 . ?
O1 C6 1.354(3) . ?
O2 H2 0.8200 . ?
O2 C4 1.357(3) . ?
C1 C2 1.373(4) . ?
C1 C6 1.390(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.378(4) . ?
C3 C4 1.391(3) . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
N1 C7 1.331(4) . ?
N1 C11 1.325(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(4) . ?
C9 C10 1.377(4) . ?
C9 C12 1.445(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.186(4) . ?
C13 C14 1.437(4) . ?
C14 C15 1.378(4) . ?
C14 C19 1.384(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.362(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.364(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(4) . ?
C19 H19 0.9300 . ?
N2 C20 1.331(4) . ?
N2 C24 1.332(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(4) . ?
C22 C23 1.386(4) . ?
C22 C25 1.432(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.367(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.187(3) . ?
C26 C27 1.439(4) . ?
C27 C28 1.385(4) . ?
C27 C32 1.387(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.376(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.368(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.370(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(4) . ?
C32 H32 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
C6 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C2 C1 Br1 119.38(19) . . ?
C2 C1 C6 120.7(2) . . ?
C6 C1 Br1 120.0(2) . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.2(2) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 Br2 119.62(19) . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 Br2 119.9(2) . . ?
O2 C4 C3 119.0(2) . . ?
O2 C4 C5 122.6(2) . . ?
C5 C4 C3 118.4(3) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.1(2) . . ?
C6 C5 H5 119.0 . . ?
O1 C6 C1 119.0(2) . . ?
O1 C6 C5 122.8(2) . . ?
C5 C6 C1 118.2(2) . . ?
C11 N1 C7 116.4(3) . . ?
N1 C7 H7 118.1 . . ?
N1 C7 C8 123.9(3) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C12 121.7(3) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 C12 120.3(3) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(3) . . ?
C11 C10 H10 120.7 . . ?
N1 C11 C10 124.1(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C13 C12 C9 178.7(3) . . ?
C12 C13 C14 178.2(4) . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 C19 118.8(3) . . ?
C19 C14 C13 121.3(3) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.5(3) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 N2 C24 116.3(3) . . ?
N2 C20 H20 118.3 . . ?
N2 C20 C21 123.4(3) . . ?
C21 C20 H20 118.3 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 116.9(3) . . ?
C21 C22 C25 120.9(3) . . ?
C23 C22 C25 122.2(3) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23 120.5 . . ?
N2 C24 C23 124.5(3) . . ?
N2 C24 H24 117.7 . . ?
C23 C24 H24 117.7 . . ?
C26 C25 C22 176.2(3) . . ?
C25 C26 C27 177.4(3) . . ?
C28 C27 C26 119.0(3) . . ?
C28 C27 C32 119.3(3) . . ?
C32 C27 C26 121.7(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120.1(3) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.7(3) . . ?
C32 C31 H31 119.7 . . ?
C27 C32 H32 120.2 . . ?
C31 C32 C27 119.5(3) . . ?
C31 C32 H32 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.94 2.750(3) 169.8 . yes
O2 H2 N2 0.82 1.91 2.726(3) 169.9 . yes

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
Br1 C1 C2 C3 179.1(2) . . . . ?
Br1 C1 C6 O1 1.5(4) . . . . ?
Br1 C1 C6 C5 -178.5(2) . . . . ?
Br2 C3 C4 O2 -0.8(4) . . . . ?
Br2 C3 C4 C5 -179.8(2) . . . . ?
O2 C4 C5 C6 -178.5(3) . . . . ?
C1 C2 C3 Br2 179.5(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C1 C6 O1 -179.6(3) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C3 C4 O2 179.1(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 O1 179.2(3) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
N1 C7 C8 C9 -1.1(5) . . . . ?
C7 N1 C11 C10 -0.5(5) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C7 C8 C9 C12 179.9(3) . . . . ?
C8 C9 C10 C11 1.9(4) . . . . ?
C9 C10 C11 N1 -1.3(5) . . . . ?
C11 N1 C7 C8 1.8(5) . . . . ?
C12 C9 C10 C11 -178.8(3) . . . . ?
C13 C14 C15 C16 179.3(3) . . . . ?
C13 C14 C19 C18 -179.0(3) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C14 C19 C18 0.4(5) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C14 -0.4(5) . . . . ?
C19 C14 C15 C16 -0.1(4) . . . . ?
N2 C20 C21 C22 -0.8(5) . . . . ?
C20 N2 C24 C23 -0.1(5) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
C20 C21 C22 C25 178.1(3) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 N2 -0.5(5) . . . . ?
C24 N2 C20 C21 0.7(4) . . . . ?
C25 C22 C23 C24 -177.5(3) . . . . ?
C26 C27 C28 C29 179.8(3) . . . . ?
C26 C27 C32 C31 180.0(3) . . . . ?
C27 C28 C29 C30 0.9(5) . . . . ?
C28 C27 C32 C31 0.6(4) . . . . ?
C28 C29 C30 C31 -0.8(5) . . . . ?
C29 C30 C31 C32 0.6(5) . . . . ?
C30 C31 C32 C27 -0.5(5) . . . . ?
C32 C27 C28 C29 -0.8(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_08_230
_database_code_depnum_ccdc_archive 'CCDC 2420453'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10.25 N, C13 H10.32 N, C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H24.57 Br2 N2 O2'
_chemical_formula_weight         628.93
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8565(6)
_cell_length_b                   11.0401(5)
_cell_length_c                   11.6972(6)
_cell_angle_alpha                91.8880(10)
_cell_angle_beta                 97.441(2)
_cell_angle_gamma                91.8380(10)
_cell_volume                     1388.49(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    230.00
_cell_measurement_theta_max      25.976
_cell_measurement_theta_min      2.596
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0865 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.8609.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             633
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.155
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            43433
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.409
_diffrn_ambient_temperature      230.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4416
_reflns_number_total             5576
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5576
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+0.6199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0740
_refine_special_details          
'In this structure, there was a mixture of 4-phenylethynyl)pyridine (A sites) and 4-stilbazole (B-sites). At this temperature, the refined occupancies of the A and B sites for molecules containing nitrogen atom N1 or N2 were 0.37:0.63 and 0.34:0.66, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, SIMU, RIGU, free variable DFIX and AFIX restraints and constraints were applied where necessary.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C12A-C13A = C25A-C26A
 1.15574 with sigma of 0.02
 C12B-C13B = C25B-C26B
 1.33768 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25A \\sim C25B \\sim C26A \\sim C26B: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.02 within 2A
C9 \\sim C12B \\sim C12A \\sim C13A \\sim C13B \\sim C14A \\sim C15A \\sim C16A
\\sim C17A \\sim C18A \\sim C19A \\sim C14B \\sim C15B \\sim C17B \\sim C16B
\\sim C18B \\sim C19B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C25B, C25A, C26A, C26B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 C9, C12B, C12A, C13A, C13B, C14A, C15A, C16A, C17A, C18A, C19A, C14B, C15B,
 C17B, C16B, C18B, C19B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C19B)=Sof(H19B)=
 Sof(C18B)=Sof(H18B)=Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=
 Sof(H15B)=1-FVAR(1)
 Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=FVAR(1)
 Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=1-FVAR(2)
 Sof(C25A)=Sof(C26A)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C19A(H19A), C18A(H18A),
 C17A(H17A), C16A(H16A), C15A(H15A), C12B(H12B), C13B(H13B), C19B(H19B),
 C18B(H18B), C17B(H17B), C16B(H16B), C15B(H15B), C20(H20), C21(H21), C23(H23),
 C24(H24), C25B(H25B), C26B(H26B), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32)
6.b Fitted hexagon refined as free rotating group:
 C14A(C19A,C18A,C17A,C16A,C15A), C14B(C19B,C18B,C17B,C16B,C15B)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72828(2) -0.04193(2) -0.40240(2) 0.05340(11) Uani 1 1 d . . . . .
Br2 Br 0.32523(2) 0.24348(2) -0.31258(2) 0.05516(11) Uani 1 1 d . . . . .
O1 O 0.79685(16) -0.00605(17) -0.14546(14) 0.0560(5) Uani 1 1 d . . . . .
H1 H 0.818718 0.008929 -0.074741 0.084 Uiso 1 1 calc R U . . .
O2 O 0.44619(17) 0.22331(18) -0.06751(15) 0.0615(5) Uani 1 1 d . . . . .
H2 H 0.486963 0.229037 -0.001320 0.092 Uiso 1 1 calc R U . . .
N1 N 0.8803(2) 0.0501(2) 0.07707(17) 0.0563(6) Uani 1 1 d . . . . .
C1 C 0.6430(2) 0.0445(2) -0.29591(18) 0.0408(5) Uani 1 1 d . . . . .
C2 C 0.5348(2) 0.10063(19) -0.33523(18) 0.0416(5) Uani 1 1 d . . . . .
H2A H 0.504616 0.097870 -0.415261 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4704(2) 0.16100(19) -0.2576(2) 0.0414(5) Uani 1 1 d . . . . .
C4 C 0.5127(2) 0.1649(2) -0.14014(19) 0.0442(5) Uani 1 1 d . . . . .
C5 C 0.6217(2) 0.1076(2) -0.10258(19) 0.0461(5) Uani 1 1 d . . . . .
H5 H 0.650775 0.108657 -0.022356 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6894(2) 0.0487(2) -0.17909(19) 0.0423(5) Uani 1 1 d . . . . .
C7 C 0.8452(3) -0.0120(3) 0.1628(2) 0.0633(7) Uani 1 1 d . . . . .
H7 H 0.799620 -0.086505 0.144710 0.076 Uiso 1 1 calc R U . . .
C8 C 0.8715(3) 0.0260(3) 0.2769(2) 0.0654(7) Uani 1 1 d . . . . .
H8 H 0.845216 -0.022820 0.335305 0.078 Uiso 1 1 calc R U . . .
C9 C 0.9358(2) 0.1347(2) 0.3067(2) 0.0509(6) Uani 1 1 d . U . . .
C10 C 0.9754(3) 0.1975(3) 0.2178(2) 0.0607(7) Uani 1 1 d . . . . .
H10 H 1.022318 0.271647 0.233354 0.073 Uiso 1 1 calc R U . . .
C11 C 0.9465(3) 0.1523(3) 0.1062(2) 0.0654(7) Uani 1 1 d . . . . .
H11 H 0.975635 0.196836 0.046358 0.078 Uiso 1 1 calc R U . . .
C12A C 0.9687(17) 0.1963(15) 0.4143(13) 0.055(2) Uani 0.374(13) 1 d D U P A 1
C13A C 0.9860(12) 0.2418(12) 0.5055(10) 0.054(2) Uani 0.374(13) 1 d D U P A 1
C14A C 1.0078(15) 0.3066(11) 0.6094(6) 0.0529(18) Uani 0.374(13) 1 d G U P A 1
C19A C 1.0699(14) 0.4191(11) 0.6140(7) 0.0581(19) Uani 0.374(13) 1 d G U P A 1
H19A H 1.098046 0.449600 0.546567 0.070 Uiso 0.374(13) 1 calc R U P A 1
C18A C 1.0908(10) 0.4870(8) 0.7173(10) 0.0588(19) Uani 0.374(13) 1 d G U P A 1
H18A H 1.133237 0.563887 0.720493 0.071 Uiso 0.374(13) 1 calc R U P A 1
C17A C 1.0496(9) 0.4424(10) 0.8160(6) 0.058(2) Uani 0.374(13) 1 d G U P A 1
H17A H 1.063886 0.488810 0.886631 0.070 Uiso 0.374(13) 1 calc R U P A 1
C16A C 0.9875(10) 0.3299(10) 0.8114(6) 0.0617(19) Uani 0.374(13) 1 d G U P A 1
H16A H 0.959345 0.299444 0.878844 0.074 Uiso 0.374(13) 1 calc R U P A 1
C15A C 0.9666(12) 0.2620(8) 0.7081(9) 0.0603(18) Uani 0.374(13) 1 d G U P A 1
H15A H 0.924153 0.185154 0.704919 0.072 Uiso 0.374(13) 1 calc R U P A 1
C12B C 0.9505(9) 0.1694(8) 0.4323(7) 0.0500(15) Uani 0.626(13) 1 d D U P A 2
H12B H 0.918872 0.114361 0.482991 0.060 Uiso 0.626(13) 1 calc R U P A 2
C13B C 1.0051(7) 0.2727(6) 0.4774(6) 0.0475(13) Uani 0.626(13) 1 d D U P A 2
H13B H 1.041327 0.324429 0.426666 0.057 Uiso 0.626(13) 1 calc R U P A 2
C14B C 1.0143(8) 0.3147(6) 0.6023(3) 0.0521(12) Uani 0.626(13) 1 d G U P A 2
C19B C 1.0755(7) 0.4244(6) 0.6388(5) 0.0528(12) Uani 0.626(13) 1 d G U P A 2
H19B H 1.112626 0.472070 0.585451 0.063 Uiso 0.626(13) 1 calc R U P A 2
C18B C 1.0822(6) 0.4645(5) 0.7534(5) 0.0570(13) Uani 0.626(13) 1 d G U P A 2
H18B H 1.123943 0.539482 0.778421 0.068 Uiso 0.626(13) 1 calc R U P A 2
C17B C 1.0278(5) 0.3947(8) 0.8315(3) 0.0620(15) Uani 0.626(13) 1 d G U P A 2
H17B H 1.032388 0.422118 0.909870 0.074 Uiso 0.626(13) 1 calc R U P A 2
C16B C 0.9667(6) 0.2850(7) 0.7950(4) 0.0698(14) Uani 0.626(13) 1 d G U P A 2
H16B H 0.929515 0.237340 0.848352 0.084 Uiso 0.626(13) 1 calc R U P A 2
C15B C 0.9600(7) 0.2449(5) 0.6804(5) 0.0643(14) Uani 0.626(13) 1 d G U P A 2
H15B H 0.918198 0.169925 0.655382 0.077 Uiso 0.626(13) 1 calc R U P A 2
N2 N 0.56603(19) 0.26152(19) 0.14809(17) 0.0522(5) Uani 1 1 d . . . . .
C20 C 0.5830(3) 0.1802(2) 0.2302(2) 0.0554(6) Uani 1 1 d . . . . .
H20 H 0.572485 0.096635 0.207878 0.066 Uiso 1 1 calc R U . . .
C21 C 0.6148(3) 0.2109(2) 0.3451(2) 0.0558(6) Uani 1 1 d . . . . .
H21 H 0.627457 0.148979 0.399488 0.067 Uiso 1 1 calc R U . . .
C22 C 0.6285(2) 0.3316(2) 0.3822(2) 0.0494(6) Uani 1 1 d . . . . .
C23 C 0.6104(2) 0.4160(2) 0.2959(2) 0.0551(6) Uani 1 1 d . . . . .
H23 H 0.618985 0.500281 0.315673 0.066 Uiso 1 1 calc R U . . .
C24 C 0.5803(2) 0.3780(2) 0.1831(2) 0.0567(6) Uani 1 1 d . . . . .
H24 H 0.568965 0.437815 0.126424 0.068 Uiso 1 1 calc R U . . .
C25A C 0.656(3) 0.388(2) 0.4900(17) 0.055(4) Uani 0.34(3) 1 d D U P B 1
C26A C 0.6762(18) 0.431(2) 0.5821(14) 0.054(3) Uani 0.34(3) 1 d D U P B 1
C25B C 0.6588(13) 0.3570(8) 0.5101(8) 0.0467(17) Uani 0.66(3) 1 d D U P B 2
H25B H 0.672496 0.290523 0.559167 0.056 Uiso 0.66(3) 1 calc R U P B 2
C26B C 0.6673(9) 0.4702(8) 0.5576(8) 0.0458(15) Uani 0.66(3) 1 d D U P B 2
H26B H 0.656466 0.536006 0.507393 0.055 Uiso 0.66(3) 1 calc R U P B 2
C27 C 0.6929(2) 0.4990(2) 0.6855(2) 0.0541(6) Uani 1 1 d . . . . .
C28 C 0.6917(3) 0.4201(3) 0.7747(3) 0.0646(7) Uani 1 1 d . . . . .
H28 H 0.678854 0.335574 0.757717 0.078 Uiso 1 1 calc R U . . .
C29 C 0.7089(3) 0.4625(3) 0.8879(3) 0.0741(8) Uani 1 1 d . . . . .
H29 H 0.706754 0.407352 0.948377 0.089 Uiso 1 1 calc R U . . .
C30 C 0.7291(3) 0.5849(3) 0.9137(3) 0.0763(9) Uani 1 1 d . . . . .
H30 H 0.741148 0.614275 0.991700 0.092 Uiso 1 1 calc R U . . .
C31 C 0.7319(3) 0.6639(3) 0.8262(3) 0.0717(9) Uani 1 1 d . . . . .
H31 H 0.746503 0.748108 0.843816 0.086 Uiso 1 1 calc R U . . .
C32 C 0.7137(3) 0.6222(3) 0.7127(3) 0.0625(7) Uani 1 1 d . . . . .
H32 H 0.715268 0.677965 0.652762 0.075 Uiso 1 1 calc R U . . .


_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(2) . ?
Br2 C3 1.896(2) . ?
O1 H1 0.8400 . ?
O1 C6 1.350(3) . ?
O2 H2 0.8400 . ?
O2 C4 1.346(3) . ?
N1 C7 1.322(4) . ?
N1 C11 1.328(4) . ?
C1 C2 1.379(3) . ?
C1 C6 1.393(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.382(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(4) . ?
C9 C10 1.375(4) . ?
C9 C12A 1.409(16) . ?
C9 C12B 1.493(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(4) . ?
C11 H11 0.9500 . ?
C12A C13A 1.16(2) . ?
C13A C14A 1.379(12) . ?
C14A C19A 1.3900 . ?
C14A C15A 1.3900 . ?
C19A H19A 0.9500 . ?
C19A C18A 1.3900 . ?
C18A H18A 0.9500 . ?
C18A C17A 1.3900 . ?
C17A H17A 0.9500 . ?
C17A C16A 1.3900 . ?
C16A H16A 0.9500 . ?
C16A C15A 1.3900 . ?
C15A H15A 0.9500 . ?
C12B H12B 0.9500 . ?
C12B C13B 1.328(12) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.508(7) . ?
C14B C19B 1.3900 . ?
C14B C15B 1.3900 . ?
C19B H19B 0.9500 . ?
C19B C18B 1.3900 . ?
C18B H18B 0.9500 . ?
C18B C17B 1.3900 . ?
C17B H17B 0.9500 . ?
C17B C16B 1.3900 . ?
C16B H16B 0.9500 . ?
C16B C15B 1.3900 . ?
C15B H15B 0.9500 . ?
N2 C20 1.336(3) . ?
N2 C24 1.335(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.371(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 C23 1.396(4) . ?
C22 C25A 1.379(19) . ?
C22 C25B 1.504(10) . ?
C23 H23 0.9500 . ?
C23 C24 1.366(4) . ?
C24 H24 0.9500 . ?
C25A C26A 1.16(3) . ?
C26A C27 1.390(14) . ?
C25B H25B 0.9500 . ?
C25B C26B 1.347(14) . ?
C26B H26B 0.9500 . ?
C26B C27 1.507(9) . ?
C27 C28 1.383(4) . ?
C27 C32 1.391(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.379(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.369(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.377(4) . ?
C32 H32 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
C6 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 116.4(2) . . ?
C2 C1 Br1 119.41(16) . . ?
C2 C1 C6 121.0(2) . . ?
C6 C1 Br1 119.57(17) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 Br2 119.53(17) . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 Br2 119.56(17) . . ?
O2 C4 C3 118.9(2) . . ?
O2 C4 C5 122.7(2) . . ?
C5 C4 C3 118.4(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
O1 C6 C1 118.6(2) . . ?
O1 C6 C5 123.2(2) . . ?
C5 C6 C1 118.2(2) . . ?
N1 C7 H7 118.3 . . ?
N1 C7 C8 123.3(3) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C12A 131.4(7) . . ?
C8 C9 C12B 114.8(4) . . ?
C10 C9 C8 116.5(2) . . ?
C10 C9 C12A 112.1(7) . . ?
C10 C9 C12B 128.7(4) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
N1 C11 C10 124.0(3) . . ?
N1 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C13A C12A C9 173.7(19) . . ?
C12A C13A C14A 174.5(18) . . ?
C13A C14A C19A 119.0(8) . . ?
C13A C14A C15A 121.0(8) . . ?
C19A C14A C15A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C9 C12B H12B 118.0 . . ?
C13B C12B C9 124.0(8) . . ?
C13B C12B H12B 118.0 . . ?
C12B C13B H13B 117.2 . . ?
C12B C13B C14B 125.6(8) . . ?
C14B C13B H13B 117.2 . . ?
C19B C14B C13B 119.9(4) . . ?
C19B C14B C15B 120.0 . . ?
C15B C14B C13B 120.1(4) . . ?
C14B C19B H19B 120.0 . . ?
C14B C19B C18B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C24 N2 C20 116.4(2) . . ?
N2 C20 H20 118.2 . . ?
N2 C20 C21 123.6(2) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 115.8(2) . . ?
C21 C22 C25B 116.7(4) . . ?
C23 C22 C25B 127.5(4) . . ?
C25A C22 C21 132.7(11) . . ?
C25A C22 C23 111.6(11) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
N2 C24 C23 123.6(2) . . ?
N2 C24 H24 118.2 . . ?
C23 C24 H24 118.2 . . ?
C26A C25A C22 178(3) . . ?
C25A C26A C27 171(3) . . ?
C22 C25B H25B 118.7 . . ?
C26B C25B C22 122.5(12) . . ?
C26B C25B H25B 118.7 . . ?
C25B C26B H26B 117.9 . . ?
C25B C26B C27 124.1(12) . . ?
C27 C26B H26B 117.9 . . ?
C26A C27 C32 133.4(11) . . ?
C28 C27 C26A 108.2(11) . . ?
C28 C27 C26B 128.1(4) . . ?
C28 C27 C32 118.4(3) . . ?
C32 C27 C26B 113.4(4) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.7(3) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.6(3) . . ?
C32 C31 H31 119.7 . . ?
C27 C32 H32 119.8 . . ?
C31 C32 C27 120.4(3) . . ?
C31 C32 H32 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.85 2.688(3) 174.4 . yes
O2 H2 N2 0.84 1.86 2.697(3) 172.1 . yes

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
Br1 C1 C2 C3 178.28(16) . . . . ?
Br1 C1 C6 O1 2.1(3) . . . . ?
Br1 C1 C6 C5 -176.89(17) . . . . ?
Br2 C3 C4 O2 2.7(3) . . . . ?
Br2 C3 C4 C5 -177.64(17) . . . . ?
O2 C4 C5 C6 -179.4(2) . . . . ?
N1 C7 C8 C9 1.0(5) . . . . ?
C1 C2 C3 Br2 177.56(16) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C1 C6 O1 -178.9(2) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
C2 C3 C4 O2 -179.1(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 O1 178.8(2) . . . . ?
C4 C5 C6 C1 -2.2(4) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 N1 C11 C10 -2.5(4) . . . . ?
C7 C8 C9 C10 -2.8(4) . . . . ?
C7 C8 C9 C12A 176.4(10) . . . . ?
C7 C8 C9 C12B 175.9(5) . . . . ?
C8 C9 C10 C11 2.0(4) . . . . ?
C8 C9 C12B C13B -177.2(8) . . . . ?
C9 C10 C11 N1 0.7(5) . . . . ?
C9 C12B C13B C14B 175.8(7) . . . . ?
C10 C9 C12B C13B 1.3(13) . . . . ?
C11 N1 C7 C8 1.6(4) . . . . ?
C12A C9 C10 C11 -177.4(9) . . . . ?
C13A C14A C19A C18A 178.8(14) . . . . ?
C13A C14A C15A C16A -178.8(14) . . . . ?
C14A C19A C18A C17A 0.0 . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?
C19A C18A C17A C16A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C17A C16A C15A C14A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C12B C9 C10 C11 -176.5(6) . . . . ?
C12B C13B C14B C19B 179.2(8) . . . . ?
C12B C13B C14B C15B -1.9(12) . . . . ?
C13B C14B C19B C18B 178.8(7) . . . . ?
C13B C14B C15B C16B -178.8(7) . . . . ?
C14B C19B C18B C17B 0.0 . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C19B C18B C17B C16B 0.0 . . . . ?
C18B C17B C16B C15B 0.0 . . . . ?
C17B C16B C15B C14B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
N2 C20 C21 C22 1.4(4) . . . . ?
C20 N2 C24 C23 -0.1(4) . . . . ?
C20 C21 C22 C23 -1.2(4) . . . . ?
C20 C21 C22 C25A 177.8(18) . . . . ?
C20 C21 C22 C25B 177.8(7) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C21 C22 C25B C26B -176.0(11) . . . . ?
C22 C23 C24 N2 0.3(4) . . . . ?
C22 C25B C26B C27 177.7(6) . . . . ?
C23 C22 C25B C26B 2.8(18) . . . . ?
C24 N2 C20 C21 -0.7(4) . . . . ?
C25A C22 C23 C24 -178.8(14) . . . . ?
C26A C27 C28 C29 178.7(9) . . . . ?
C26A C27 C32 C31 -177.4(11) . . . . ?
C25B C22 C23 C24 -178.4(7) . . . . ?
C25B C26B C27 C28 -11.5(15) . . . . ?
C25B C26B C27 C32 172.0(11) . . . . ?
C26B C27 C28 C29 -175.5(5) . . . . ?
C26B C27 C32 C31 176.6(4) . . . . ?
C27 C28 C29 C30 -0.8(5) . . . . ?
C28 C27 C32 C31 -0.3(4) . . . . ?
C28 C29 C30 C31 0.1(5) . . . . ?
C29 C30 C31 C32 0.5(5) . . . . ?
C30 C31 C32 C27 -0.4(4) . . . . ?
C32 C27 C28 C29 0.9(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_08_190
_database_code_depnum_ccdc_archive 'CCDC 2420455'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10.28 N, C13 H10.34 N, C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H24.62 Br2 N2 O2'
_chemical_formula_weight         628.99
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8084(5)
_cell_length_b                   11.0217(4)
_cell_length_c                   11.6874(6)
_cell_angle_alpha                91.6890(10)
_cell_angle_beta                 97.496(2)
_cell_angle_gamma                91.8790(10)
_cell_volume                     1378.84(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    190.00
_cell_measurement_theta_max      26.740
_cell_measurement_theta_min      2.595
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.972
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0935 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.8682.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             633
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.155
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45409
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_min         2.415
_diffrn_ambient_temperature      190.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4885
_reflns_number_total             5965
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5965
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0185P)²+0.6793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0694
_refine_special_details          
'In this structure, there was a mixture of 4-phenylethynyl)pyridine (A sites) and 4-stilbazole (B-sites). At this temperature, the refined occupancies of the A and B sites for molecules containing nitrogen atom N1 or N2 were 0.36:0.64 and 0.33:0.67, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, SIMU, RIGU, free variable DFIX and AFIX restraints and constraints were applied where necessary.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C12A-C13A = C25A-C26A
 1.21152 with sigma of 0.02
 C12B-C13B = C25B-C26B
 1.32543 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25A \\sim C25B \\sim C26A \\sim C26B: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.02 within 2A
C9 \\sim C12B \\sim C12A \\sim C13A \\sim C13B \\sim C14A \\sim C15A \\sim C16A
\\sim C17A \\sim C18A \\sim C19A \\sim C14B \\sim C15B \\sim C17B \\sim C16B
\\sim C18B \\sim C19B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C25B, C25A, C26A, C26B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 C9, C12B, C12A, C13A, C13B, C14A, C15A, C16A, C17A, C18A, C19A, C14B, C15B,
 C17B, C16B, C18B, C19B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C19B)=Sof(H19B)=
 Sof(C18B)=Sof(H18B)=Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=
 Sof(H15B)=1-FVAR(1)
 Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=FVAR(1)
 Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=1-FVAR(2)
 Sof(C25A)=Sof(C26A)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C19A(H19A), C18A(H18A),
 C17A(H17A), C16A(H16A), C15A(H15A), C12B(H12B), C13B(H13B), C19B(H19B),
 C18B(H18B), C17B(H17B), C16B(H16B), C15B(H15B), C20(H20), C21(H21), C23(H23),
 C24(H24), C25B(H25B), C26B(H26B), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32)
6.b Fitted hexagon refined as free rotating group:
 C14A(C19A,C18A,C17A,C16A,C15A), C14B(C19B,C18B,C17B,C16B,C15B)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72895(2) -0.04225(2) -0.40236(2) 0.04378(9) Uani 1 1 d . . . . .
Br2 Br 0.32415(2) 0.24414(2) -0.31369(2) 0.04524(9) Uani 1 1 d . . . . .
O1 O 0.79782(14) -0.00644(15) -0.14526(12) 0.0457(4) Uani 1 1 d . . . . .
H1 H 0.821734 0.011488 -0.075347 0.069 Uiso 1 1 calc R U . . .
O2 O 0.44524(15) 0.22328(16) -0.06798(14) 0.0508(4) Uani 1 1 d . . . . .
H2 H 0.487106 0.230568 -0.002197 0.076 Uiso 1 1 calc R U . . .
N1 N 0.88113(18) 0.04981(19) 0.07707(15) 0.0469(5) Uani 1 1 d . . . . .
C1 C 0.64334(19) 0.04436(18) -0.29617(17) 0.0346(4) Uani 1 1 d . . . . .
C2 C 0.53429(19) 0.10082(17) -0.33574(17) 0.0343(4) Uani 1 1 d . . . . .
H2A H 0.503972 0.098148 -0.415848 0.041 Uiso 1 1 calc R U . . .
C3 C 0.46969(19) 0.16105(17) -0.25840(18) 0.0346(4) Uani 1 1 d . . . . .
C4 C 0.51176(19) 0.16496(18) -0.14058(18) 0.0371(4) Uani 1 1 d . . . . .
C5 C 0.6219(2) 0.10741(19) -0.10275(17) 0.0385(5) Uani 1 1 d . . . . .
H5 H 0.651342 0.108720 -0.022474 0.046 Uiso 1 1 calc R U . . .
C6 C 0.68989(19) 0.04823(18) -0.17911(17) 0.0351(4) Uani 1 1 d . . . . .
C7 C 0.8457(2) -0.0127(2) 0.1628(2) 0.0518(6) Uani 1 1 d . . . . .
H7 H 0.800232 -0.087463 0.144590 0.062 Uiso 1 1 calc R U . . .
C8 C 0.8714(3) 0.0250(2) 0.2771(2) 0.0539(6) Uani 1 1 d . . . . .
H8 H 0.844664 -0.023903 0.335494 0.065 Uiso 1 1 calc R U . . .
C9 C 0.9360(2) 0.1342(2) 0.30694(18) 0.0419(5) Uani 1 1 d . U . . .
C10 C 0.9761(2) 0.1982(2) 0.2180(2) 0.0499(6) Uani 1 1 d . . . . .
H10 H 1.022870 0.272649 0.233558 0.060 Uiso 1 1 calc R U . . .
C11 C 0.9472(2) 0.1526(3) 0.1065(2) 0.0551(6) Uani 1 1 d . . . . .
H11 H 0.976269 0.197464 0.046500 0.066 Uiso 1 1 calc R U . . .
C12A C 0.9683(16) 0.1943(15) 0.4131(12) 0.046(2) Uani 0.358(12) 1 d D U P A 1
C13A C 0.9864(11) 0.2454(11) 0.5065(10) 0.0436(19) Uani 0.358(12) 1 d D U P A 1
C14A C 1.0072(15) 0.3071(11) 0.6106(6) 0.0436(17) Uani 0.358(12) 1 d G U P A 1
C19A C 1.0703(14) 0.4194(11) 0.6154(7) 0.0465(18) Uani 0.358(12) 1 d G U P A 1
H19A H 1.099221 0.449803 0.548034 0.056 Uiso 0.358(12) 1 calc R U P A 1
C18A C 1.0911(10) 0.4873(8) 0.7187(9) 0.0488(18) Uani 0.358(12) 1 d G U P A 1
H18A H 1.134233 0.564052 0.721905 0.059 Uiso 0.358(12) 1 calc R U P A 1
C17A C 1.0488(9) 0.4428(9) 0.8172(6) 0.0495(19) Uani 0.358(12) 1 d G U P A 1
H17A H 1.062967 0.489207 0.887804 0.059 Uiso 0.358(12) 1 calc R U P A 1
C16A C 0.9856(9) 0.3305(10) 0.8125(6) 0.0513(18) Uani 0.358(12) 1 d G U P A 1
H16A H 0.956686 0.300111 0.879832 0.062 Uiso 0.358(12) 1 calc R U P A 1
C15A C 0.9648(11) 0.2626(8) 0.7092(9) 0.0511(18) Uani 0.358(12) 1 d G U P A 1
H15A H 0.921672 0.185860 0.705962 0.061 Uiso 0.358(12) 1 calc R U P A 1
C12B C 0.9513(8) 0.1700(7) 0.4327(6) 0.0408(13) Uani 0.642(12) 1 d D U P A 2
H12B H 0.919713 0.115170 0.483990 0.049 Uiso 0.642(12) 1 calc R U P A 2
C13B C 1.0058(6) 0.2727(5) 0.4770(5) 0.0398(11) Uani 0.642(12) 1 d D U P A 2
H13B H 1.042698 0.324244 0.426085 0.048 Uiso 0.642(12) 1 calc R U P A 2
C14B C 1.0146(8) 0.3154(6) 0.6022(3) 0.0418(11) Uani 0.642(12) 1 d G U P A 2
C19B C 1.0756(7) 0.4257(5) 0.6381(4) 0.0427(10) Uani 0.642(12) 1 d G U P A 2
H19B H 1.112792 0.473359 0.584457 0.051 Uiso 0.642(12) 1 calc R U P A 2
C18B C 1.0821(5) 0.4662(5) 0.7526(5) 0.0473(12) Uani 0.642(12) 1 d G U P A 2
H18B H 1.123781 0.541542 0.777155 0.057 Uiso 0.642(12) 1 calc R U P A 2
C17B C 1.0277(5) 0.3964(7) 0.8311(3) 0.0518(13) Uani 0.642(12) 1 d G U P A 2
H17B H 1.032166 0.424129 0.909358 0.062 Uiso 0.642(12) 1 calc R U P A 2
C16B C 0.9668(5) 0.2862(6) 0.7952(4) 0.0587(13) Uani 0.642(12) 1 d G U P A 2
H16B H 0.929562 0.238533 0.848863 0.070 Uiso 0.642(12) 1 calc R U P A 2
C15B C 0.9602(6) 0.2457(5) 0.6807(5) 0.0534(12) Uani 0.642(12) 1 d G U P A 2
H15B H 0.918572 0.170348 0.656165 0.064 Uiso 0.642(12) 1 calc R U P A 2
N2 N 0.56572(17) 0.26113(17) 0.14719(15) 0.0432(4) Uani 1 1 d . . . . .
C20 C 0.5832(2) 0.1794(2) 0.2298(2) 0.0462(5) Uani 1 1 d . . . . .
H20 H 0.573199 0.095662 0.207522 0.055 Uiso 1 1 calc R U . . .
C21 C 0.6149(2) 0.2099(2) 0.3451(2) 0.0464(5) Uani 1 1 d . . . . .
H21 H 0.627309 0.147926 0.399821 0.056 Uiso 1 1 calc R U . . .
C22 C 0.6286(2) 0.3310(2) 0.38156(19) 0.0418(5) Uani 1 1 d . . . . .
C23 C 0.6104(2) 0.4162(2) 0.2951(2) 0.0467(5) Uani 1 1 d . . . . .
H23 H 0.619029 0.500575 0.314885 0.056 Uiso 1 1 calc R U . . .
C24 C 0.5801(2) 0.3781(2) 0.1822(2) 0.0467(5) Uani 1 1 d . . . . .
H24 H 0.568644 0.437989 0.125408 0.056 Uiso 1 1 calc R U . . .
C25A C 0.654(2) 0.3852(18) 0.4865(15) 0.045(3) Uani 0.33(2) 1 d D U P B 1
C26A C 0.6756(14) 0.432(2) 0.5835(13) 0.046(3) Uani 0.33(2) 1 d D U P B 1
C25B C 0.6593(10) 0.3569(7) 0.5106(7) 0.0374(13) Uani 0.67(2) 1 d D U P B 2
H25B H 0.673515 0.290644 0.560284 0.045 Uiso 0.67(2) 1 calc R U P B 2
C26B C 0.6671(6) 0.4694(7) 0.5567(7) 0.0376(12) Uani 0.67(2) 1 d D U P B 2
H26B H 0.656091 0.535051 0.505897 0.045 Uiso 0.67(2) 1 calc R U P B 2
C27 C 0.6927(2) 0.4987(2) 0.6855(2) 0.0456(5) Uani 1 1 d . . . . .
C28 C 0.6910(2) 0.4196(2) 0.7748(2) 0.0548(6) Uani 1 1 d . . . . .
H28 H 0.677533 0.334955 0.757932 0.066 Uiso 1 1 calc R U . . .
C29 C 0.7086(3) 0.4618(3) 0.8880(2) 0.0616(7) Uani 1 1 d . . . . .
H29 H 0.706948 0.406461 0.948574 0.074 Uiso 1 1 calc R U . . .
C30 C 0.7287(2) 0.5845(3) 0.9136(2) 0.0636(8) Uani 1 1 d . . . . .
H30 H 0.740451 0.613601 0.991724 0.076 Uiso 1 1 calc R U . . .
C31 C 0.7316(2) 0.6647(3) 0.8260(3) 0.0593(7) Uani 1 1 d . . . . .
H31 H 0.746257 0.749029 0.843505 0.071 Uiso 1 1 calc R U . . .
C32 C 0.7131(2) 0.6223(2) 0.7122(2) 0.0519(6) Uani 1 1 d . . . . .
H32 H 0.714436 0.678013 0.651823 0.062 Uiso 1 1 calc R U . . .


_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 1.896(2) . ?
Br2 C3 1.896(2) . ?
O1 H1 0.8400 . ?
O1 C6 1.349(2) . ?
O2 H2 0.8400 . ?
O2 C4 1.344(2) . ?
N1 C7 1.322(3) . ?
N1 C11 1.331(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.394(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.380(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.394(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 C10 1.381(3) . ?
C9 C12A 1.387(15) . ?
C9 C12B 1.498(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9500 . ?
C12A C13A 1.202(19) . ?
C13A C14A 1.366(11) . ?
C14A C19A 1.3900 . ?
C14A C15A 1.3900 . ?
C19A H19A 0.9500 . ?
C19A C18A 1.3900 . ?
C18A H18A 0.9500 . ?
C18A C17A 1.3900 . ?
C17A H17A 0.9500 . ?
C17A C16A 1.3900 . ?
C16A H16A 0.9500 . ?
C16A C15A 1.3900 . ?
C15A H15A 0.9500 . ?
C12B H12B 0.9500 . ?
C12B C13B 1.318(10) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.514(6) . ?
C14B C19B 1.3900 . ?
C14B C15B 1.3900 . ?
C19B H19B 0.9500 . ?
C19B C18B 1.3900 . ?
C18B H18B 0.9500 . ?
C18B C17B 1.3900 . ?
C17B H17B 0.9500 . ?
C17B C16B 1.3900 . ?
C16B H16B 0.9500 . ?
C16B C15B 1.3900 . ?
C15B H15B 0.9500 . ?
N2 C20 1.340(3) . ?
N2 C24 1.339(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(3) . ?
C22 C23 1.399(3) . ?
C22 C25A 1.340(16) . ?
C22 C25B 1.518(8) . ?
C23 H23 0.9500 . ?
C23 C24 1.368(3) . ?
C24 H24 0.9500 . ?
C25A C26A 1.22(2) . ?
C26A C27 1.372(13) . ?
C25B H25B 0.9500 . ?
C25B C26B 1.332(11) . ?
C26B H26B 0.9500 . ?
C26B C27 1.518(8) . ?
C27 C28 1.382(4) . ?
C27 C32 1.393(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.380(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.375(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.383(4) . ?
C32 H32 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
C6 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 116.4(2) . . ?
C2 C1 Br1 119.50(15) . . ?
C2 C1 C6 120.96(18) . . ?
C6 C1 Br1 119.52(15) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.75(18) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 Br2 119.59(15) . . ?
C2 C3 C4 121.05(18) . . ?
C4 C3 Br2 119.33(15) . . ?
O2 C4 C3 119.18(19) . . ?
O2 C4 C5 122.66(19) . . ?
C3 C4 C5 118.16(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.87(19) . . ?
C6 C5 H5 119.1 . . ?
O1 C6 C1 118.61(18) . . ?
O1 C6 C5 123.20(18) . . ?
C5 C6 C1 118.19(18) . . ?
N1 C7 H7 118.3 . . ?
N1 C7 C8 123.4(2) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C12A 131.2(7) . . ?
C8 C9 C12B 115.4(3) . . ?
C10 C9 C8 116.8(2) . . ?
C10 C9 C12A 112.0(7) . . ?
C10 C9 C12B 127.8(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
N1 C11 C10 124.3(2) . . ?
N1 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
C13A C12A C9 174.8(18) . . ?
C12A C13A C14A 178.1(16) . . ?
C13A C14A C19A 117.7(8) . . ?
C13A C14A C15A 122.3(8) . . ?
C19A C14A C15A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C9 C12B H12B 117.8 . . ?
C13B C12B C9 124.3(7) . . ?
C13B C12B H12B 117.8 . . ?
C12B C13B H13B 117.3 . . ?
C12B C13B C14B 125.5(7) . . ?
C14B C13B H13B 117.3 . . ?
C19B C14B C13B 119.8(3) . . ?
C19B C14B C15B 120.0 . . ?
C15B C14B C13B 120.2(3) . . ?
C14B C19B H19B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C19B C18B C17B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C24 N2 C20 116.33(19) . . ?
N2 C20 H20 118.2 . . ?
N2 C20 C21 123.6(2) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 116.2(2) . . ?
C21 C22 C25B 116.7(4) . . ?
C23 C22 C25B 127.1(4) . . ?
C25A C22 C21 132.3(9) . . ?
C25A C22 C23 111.4(9) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
N2 C24 C23 123.8(2) . . ?
N2 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
C26A C25A C22 178(3) . . ?
C25A C26A C27 172(3) . . ?
C22 C25B H25B 118.9 . . ?
C26B C25B C22 122.2(10) . . ?
C26B C25B H25B 118.9 . . ?
C25B C26B H26B 118.1 . . ?
C25B C26B C27 123.8(11) . . ?
C27 C26B H26B 118.1 . . ?
C26A C27 C28 108.0(10) . . ?
C26A C27 C32 133.3(10) . . ?
C28 C27 C26B 127.9(4) . . ?
C28 C27 C32 118.6(2) . . ?
C32 C27 C26B 113.4(4) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.1(3) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0(2) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 119.9(2) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 H32 119.7 . . ?
C31 C32 C27 120.5(3) . . ?
C31 C32 H32 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.84 2.684(2) 177.6 . yes
O2 H2 N2 0.84 1.86 2.691(2) 172.9 . yes

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
Br1 C1 C2 C3 178.16(15) . . . . ?
Br1 C1 C6 O1 2.4(3) . . . . ?
Br1 C1 C6 C5 -176.95(16) . . . . ?
Br2 C3 C4 O2 2.8(3) . . . . ?
Br2 C3 C4 C5 -177.32(16) . . . . ?
O2 C4 C5 C6 -179.6(2) . . . . ?
N1 C7 C8 C9 0.8(4) . . . . ?
C1 C2 C3 Br2 177.33(15) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C6 O1 -178.81(18) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C3 C4 O2 -179.16(19) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 O1 178.8(2) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C7 N1 C11 C10 -2.3(4) . . . . ?
C7 C8 C9 C10 -2.4(4) . . . . ?
C7 C8 C9 C12A 176.7(10) . . . . ?
C7 C8 C9 C12B 176.1(5) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
C8 C9 C12B C13B -177.3(8) . . . . ?
C9 C10 C11 N1 0.7(4) . . . . ?
C9 C12B C13B C14B 175.4(6) . . . . ?
C10 C9 C12B C13B 1.1(12) . . . . ?
C11 N1 C7 C8 1.5(4) . . . . ?
C12A C9 C10 C11 -177.6(8) . . . . ?
C13A C14A C19A C18A 178.4(13) . . . . ?
C13A C14A C15A C16A -178.3(14) . . . . ?
C14A C19A C18A C17A 0.0 . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?
C19A C18A C17A C16A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C17A C16A C15A C14A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C12B C9 C10 C11 -176.6(5) . . . . ?
C12B C13B C14B C19B 179.6(7) . . . . ?
C12B C13B C14B C15B -1.5(10) . . . . ?
C13B C14B C19B C18B 179.0(7) . . . . ?
C13B C14B C15B C16B -178.9(7) . . . . ?
C14B C19B C18B C17B 0.0 . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C19B C18B C17B C16B 0.0 . . . . ?
C18B C17B C16B C15B 0.0 . . . . ?
C17B C16B C15B C14B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
N2 C20 C21 C22 0.9(4) . . . . ?
C20 N2 C24 C23 -0.3(3) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C20 C21 C22 C25A 177.4(14) . . . . ?
C20 C21 C22 C25B 178.0(5) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C21 C22 C25B C26B -175.8(8) . . . . ?
C22 C23 C24 N2 0.2(4) . . . . ?
C22 C25B C26B C27 177.5(5) . . . . ?
C23 C22 C25B C26B 3.0(13) . . . . ?
C24 N2 C20 C21 -0.3(3) . . . . ?
C25A C22 C23 C24 -178.3(11) . . . . ?
C26A C27 C28 C29 178.7(7) . . . . ?
C26A C27 C32 C31 -177.8(9) . . . . ?
C25B C22 C23 C24 -178.4(5) . . . . ?
C25B C26B C27 C28 -11.8(11) . . . . ?
C25B C26B C27 C32 171.9(8) . . . . ?
C26B C27 C28 C29 -175.8(4) . . . . ?
C26B C27 C32 C31 176.8(3) . . . . ?
C27 C28 C29 C30 -0.2(4) . . . . ?
C28 C27 C32 C31 0.1(4) . . . . ?
C28 C29 C30 C31 -0.3(4) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
C30 C31 C32 C27 -0.6(4) . . . . ?
C32 C27 C28 C29 0.3(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'

# 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_gro23_04_210
_database_code_depnum_ccdc_archive 'CCDC 2420442'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H11 N), C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H26 Br2 N2 O2'
_chemical_formula_weight         630.37
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.766(5)
_cell_length_b                   11.097(5)
_cell_length_c                   11.629(7)
_cell_angle_alpha                92.048(11)
_cell_angle_beta                 96.699(13)
_cell_angle_gamma                92.013(11)
_cell_volume                     1377.8(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8790
_cell_measurement_temperature    210.00
_cell_measurement_theta_max      24.254
_cell_measurement_theta_min      2.497
_shelx_estimated_absorpt_T_max   0.643
_shelx_estimated_absorpt_T_min   0.593
_exptl_absorpt_coefficient_mu    2.974
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.9166.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.163
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45868
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.440
_diffrn_ambient_temperature      210.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4387
_reflns_number_total             5578
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0125(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0225P)²+0.5837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72647(2) -0.04532(2) -0.40294(2) 0.03996(10) Uani 1 1 d . . . . .
Br2 Br 0.32393(2) 0.24379(2) -0.30789(2) 0.04274(10) Uani 1 1 d . . . . .
O1 O 0.80021(16) -0.00254(17) -0.14623(14) 0.0446(4) Uani 1 1 d . . . . .
H1 H 0.826011 0.018553 -0.078188 0.067 Uiso 1 1 calc R U . . .
O2 O 0.44875(17) 0.22858(18) -0.06336(15) 0.0491(5) Uani 1 1 d . . . . .
H2 H 0.490992 0.237239 0.001015 0.074 Uiso 1 1 calc R U . . .
N1 N 0.8849(2) 0.0587(2) 0.07562(18) 0.0445(5) Uani 1 1 d . . . . .
C1 C 0.6422(2) 0.0441(2) -0.29503(19) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.5333(2) 0.0990(2) -0.33318(19) 0.0318(5) Uani 1 1 d . . . . .
H2A H 0.501959 0.093892 -0.412183 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4701(2) 0.1616(2) -0.2548(2) 0.0318(5) Uani 1 1 d . . . . .
C4 C 0.5142(2) 0.1684(2) -0.1370(2) 0.0364(5) Uani 1 1 d . . . . .
C5 C 0.6246(2) 0.1121(2) -0.1010(2) 0.0377(6) Uani 1 1 d . . . . .
H5 H 0.655045 0.115496 -0.021753 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6914(2) 0.0509(2) -0.1786(2) 0.0337(5) Uani 1 1 d . . . . .
C7 C 0.8490(3) -0.0073(3) 0.1587(2) 0.0523(7) Uani 1 1 d . . . . .
H7 H 0.805170 -0.081036 0.137449 0.063 Uiso 1 1 calc R U . . .
C8 C 0.8719(3) 0.0256(3) 0.2751(2) 0.0543(7) Uani 1 1 d . . . . .
H8 H 0.844651 -0.025580 0.330633 0.065 Uiso 1 1 calc R U . . .
C9 C 0.9349(2) 0.1337(2) 0.3099(2) 0.0384(6) Uani 1 1 d . . . . .
C10 C 0.9763(2) 0.2015(3) 0.2234(2) 0.0456(6) Uani 1 1 d . . . . .
H10 H 1.022141 0.274628 0.241978 0.055 Uiso 1 1 calc R U . . .
C11 C 0.9495(3) 0.1606(3) 0.1095(2) 0.0525(7) Uani 1 1 d . . . . .
H11 H 0.978896 0.207843 0.052102 0.063 Uiso 1 1 calc R U . . .
C12 C 0.9523(3) 0.1713(2) 0.4331(2) 0.0448(6) Uani 1 1 d . . . . .
H12 H 0.922747 0.116522 0.484383 0.054 Uiso 1 1 calc R U . . .
C13 C 1.0047(2) 0.2734(2) 0.4798(2) 0.0400(6) Uani 1 1 d . . . . .
H13 H 1.040324 0.325782 0.429781 0.048 Uiso 1 1 calc R U . . .
C14 C 1.0131(2) 0.3135(2) 0.6020(2) 0.0386(6) Uani 1 1 d . . . . .
C15 C 0.9610(3) 0.2467(3) 0.6845(2) 0.0488(7) Uani 1 1 d . . . . .
H15 H 0.919954 0.171863 0.662541 0.059 Uiso 1 1 calc R U . . .
C16 C 0.9687(3) 0.2888(3) 0.7978(2) 0.0636(9) Uani 1 1 d . . . . .
H16 H 0.932808 0.242396 0.852335 0.076 Uiso 1 1 calc R U . . .
C17 C 1.0280(3) 0.3975(3) 0.8323(3) 0.0631(9) Uani 1 1 d . . . . .
H17 H 1.032526 0.425537 0.909976 0.076 Uiso 1 1 calc R U . . .
C18 C 1.0807(3) 0.4650(3) 0.7530(3) 0.0586(8) Uani 1 1 d . . . . .
H18 H 1.122246 0.539247 0.776477 0.070 Uiso 1 1 calc R U . . .
C19 C 1.0729(2) 0.4238(2) 0.6376(2) 0.0469(7) Uani 1 1 d . . . . .
H19 H 1.108344 0.471071 0.583409 0.056 Uiso 1 1 calc R U . . .
N2 N 0.57014(19) 0.2657(2) 0.15107(18) 0.0413(5) Uani 1 1 d . . . . .
C20 C 0.5846(3) 0.1823(2) 0.2314(2) 0.0454(6) Uani 1 1 d . . . . .
H20 H 0.573432 0.100562 0.207097 0.054 Uiso 1 1 calc R U . . .
C21 C 0.6150(3) 0.2099(2) 0.3475(2) 0.0435(6) Uani 1 1 d . . . . .
H21 H 0.624929 0.147531 0.399958 0.052 Uiso 1 1 calc R U . . .
C22 C 0.6311(2) 0.3297(2) 0.3881(2) 0.0367(5) Uani 1 1 d . . . . .
C23 C 0.6159(2) 0.4163(2) 0.3033(2) 0.0407(6) Uani 1 1 d . . . . .
H23 H 0.626121 0.498772 0.324866 0.049 Uiso 1 1 calc R U . . .
C24 C 0.5864(2) 0.3811(2) 0.1892(2) 0.0426(6) Uani 1 1 d . . . . .
H24 H 0.577001 0.441378 0.134420 0.051 Uiso 1 1 calc R U . . .
C25 C 0.6593(2) 0.3600(2) 0.5123(2) 0.0392(6) Uani 1 1 d . . . . .
H25 H 0.671945 0.295569 0.562120 0.047 Uiso 1 1 calc R U . . .
C26 C 0.6685(2) 0.4708(2) 0.5607(2) 0.0402(6) Uani 1 1 d . . . . .
H26 H 0.659518 0.534613 0.509776 0.048 Uiso 1 1 calc R U . . .
C27 C 0.6912(2) 0.5047(2) 0.6845(2) 0.0391(6) Uani 1 1 d . . . . .
C28 C 0.6892(2) 0.4219(2) 0.7714(2) 0.0455(6) Uani 1 1 d . . . . .
H28 H 0.676587 0.339235 0.751376 0.055 Uiso 1 1 calc R U . . .
C29 C 0.7056(3) 0.4598(3) 0.8870(2) 0.0549(7) Uani 1 1 d . . . . .
H29 H 0.702912 0.402775 0.944679 0.066 Uiso 1 1 calc R U . . .
C30 C 0.7259(3) 0.5803(3) 0.9183(3) 0.0584(8) Uani 1 1 d . . . . .
H30 H 0.737091 0.605463 0.996989 0.070 Uiso 1 1 calc R U . . .
C31 C 0.7298(3) 0.6641(3) 0.8338(3) 0.0571(8) Uani 1 1 d . . . . .
H31 H 0.744307 0.746398 0.854983 0.069 Uiso 1 1 calc R U . . .
C32 C 0.7122(3) 0.6272(2) 0.7178(3) 0.0488(7) Uani 1 1 d . . . . .
H32 H 0.714382 0.684848 0.660771 0.059 Uiso 1 1 calc R U . . .


_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 1.903(2) . ?
Br2 C3 1.898(2) . ?
O1 H1 0.8300 . ?
O1 C6 1.352(3) . ?
O2 H2 0.8300 . ?
O2 C4 1.345(3) . ?
N1 C7 1.318(4) . ?
N1 C11 1.329(4) . ?
C1 C2 1.376(3) . ?
C1 C6 1.393(3) . ?
C2 H2A 0.9400 . ?
C2 C3 1.382(3) . ?
C3 C4 1.395(3) . ?
C4 C5 1.391(3) . ?
C5 H5 0.9400 . ?
C5 C6 1.391(3) . ?
C7 H7 0.9400 . ?
C7 C8 1.381(4) . ?
C8 H8 0.9400 . ?
C8 C9 1.381(4) . ?
C9 C10 1.382(4) . ?
C9 C12 1.466(3) . ?
C10 H10 0.9400 . ?
C10 C11 1.379(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C12 C13 1.318(4) . ?
C13 H13 0.9400 . ?
C13 C14 1.465(3) . ?
C14 C15 1.389(4) . ?
C14 C19 1.389(4) . ?
C15 H15 0.9400 . ?
C15 C16 1.374(4) . ?
C16 H16 0.9400 . ?
C16 C17 1.368(5) . ?
C17 H17 0.9400 . ?
C17 C18 1.369(5) . ?
C18 H18 0.9400 . ?
C18 C19 1.395(4) . ?
C19 H19 0.9400 . ?
N2 C20 1.339(3) . ?
N2 C24 1.339(3) . ?
C20 H20 0.9400 . ?
C20 C21 1.372(4) . ?
C21 H21 0.9400 . ?
C21 C22 1.392(3) . ?
C22 C23 1.402(3) . ?
C22 C25 1.466(3) . ?
C23 H23 0.9400 . ?
C23 C24 1.367(4) . ?
C24 H24 0.9400 . ?
C25 H25 0.9400 . ?
C25 C26 1.329(3) . ?
C26 H26 0.9400 . ?
C26 C27 1.465(3) . ?
C27 C28 1.391(4) . ?
C27 C32 1.404(3) . ?
C28 H28 0.9400 . ?
C28 C29 1.383(4) . ?
C29 H29 0.9400 . ?
C29 C30 1.377(4) . ?
C30 H30 0.9400 . ?
C30 C31 1.380(4) . ?
C31 H31 0.9400 . ?
C31 C32 1.385(4) . ?
C32 H32 0.9400 . ?

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 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 116.2(2) . . ?
C2 C1 Br1 119.40(17) . . ?
C2 C1 C6 121.4(2) . . ?
C6 C1 Br1 119.17(18) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 Br2 119.88(17) . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 Br2 119.23(18) . . ?
O2 C4 C3 119.0(2) . . ?
O2 C4 C5 122.8(2) . . ?
C5 C4 C3 118.2(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
O1 C6 C1 119.0(2) . . ?
O1 C6 C5 123.2(2) . . ?
C5 C6 C1 117.8(2) . . ?
N1 C7 H7 118.1 . . ?
N1 C7 C8 123.8(3) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 116.5(2) . . ?
C8 C9 C12 119.6(2) . . ?
C10 C9 C12 123.9(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
N1 C11 C10 124.3(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C9 C12 H12 116.4 . . ?
C13 C12 C9 127.2(3) . . ?
C13 C12 H12 116.4 . . ?
C12 C13 H13 116.7 . . ?
C12 C13 C14 126.5(3) . . ?
C14 C13 H13 116.7 . . ?
C15 C14 C13 122.7(2) . . ?
C15 C14 C19 118.0(2) . . ?
C19 C14 C13 119.3(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.5(3) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C20 N2 C24 116.5(2) . . ?
N2 C20 H20 118.3 . . ?
N2 C20 C21 123.4(2) . . ?
C21 C20 H20 118.3 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.5(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 115.6(2) . . ?
C21 C22 C25 120.9(2) . . ?
C23 C22 C25 123.5(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
N2 C24 C23 123.7(2) . . ?
N2 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
C22 C25 H25 117.2 . . ?
C26 C25 C22 125.7(2) . . ?
C26 C25 H25 117.2 . . ?
C25 C26 H26 116.3 . . ?
C25 C26 C27 127.4(2) . . ?
C27 C26 H26 116.3 . . ?
C28 C27 C26 123.4(2) . . ?
C28 C27 C32 117.9(2) . . ?
C32 C27 C26 118.6(2) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.1(3) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 H32 119.6 . . ?
C31 C32 C27 120.8(3) . . ?
C31 C32 H32 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.86 2.689(3) 177.5 . yes
O2 H2 N2 0.83 1.86 2.688(3) 173.4 . yes

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
Br1 C1 C2 C3 178.46(17) . . . . ?
Br1 C1 C6 O1 2.5(3) . . . . ?
Br1 C1 C6 C5 -177.03(18) . . . . ?
Br2 C3 C4 O2 2.9(3) . . . . ?
Br2 C3 C4 C5 -177.08(18) . . . . ?
O2 C4 C5 C6 -179.6(2) . . . . ?
N1 C7 C8 C9 0.6(5) . . . . ?
C1 C2 C3 Br2 177.09(17) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 O1 -178.6(2) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C2 C3 C4 O2 -178.9(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 O1 178.6(2) . . . . ?
C4 C5 C6 C1 -1.9(4) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 N1 C11 C10 -2.3(4) . . . . ?
C7 C8 C9 C10 -2.6(4) . . . . ?
C7 C8 C9 C12 176.4(3) . . . . ?
C8 C9 C10 C11 2.1(4) . . . . ?
C8 C9 C12 C13 -176.7(3) . . . . ?
C9 C10 C11 N1 0.3(4) . . . . ?
C9 C12 C13 C14 175.1(3) . . . . ?
C10 C9 C12 C13 2.2(4) . . . . ?
C11 N1 C7 C8 1.8(4) . . . . ?
C12 C9 C10 C11 -176.8(3) . . . . ?
C12 C13 C14 C15 -2.1(4) . . . . ?
C12 C13 C14 C19 179.4(3) . . . . ?
C13 C14 C15 C16 -178.6(3) . . . . ?
C13 C14 C19 C18 179.1(2) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C14 C19 C18 0.5(4) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C18 C19 C14 -0.8(4) . . . . ?
C19 C14 C15 C16 -0.1(4) . . . . ?
N2 C20 C21 C22 0.8(4) . . . . ?
C20 N2 C24 C23 -0.2(4) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
C20 C21 C22 C25 177.9(2) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C21 C22 C25 C26 -175.5(3) . . . . ?
C22 C23 C24 N2 0.1(4) . . . . ?
C22 C25 C26 C27 177.2(2) . . . . ?
C23 C22 C25 C26 3.2(4) . . . . ?
C24 N2 C20 C21 -0.2(4) . . . . ?
C25 C22 C23 C24 -178.3(2) . . . . ?
C25 C26 C27 C28 -9.3(4) . . . . ?
C25 C26 C27 C32 172.8(3) . . . . ?
C26 C27 C28 C29 -177.0(3) . . . . ?
C26 C27 C32 C31 177.7(2) . . . . ?
C27 C28 C29 C30 -0.9(4) . . . . ?
C28 C27 C32 C31 -0.3(4) . . . . ?
C28 C29 C30 C31 0.1(4) . . . . ?
C29 C30 C31 C32 0.6(4) . . . . ?
C30 C31 C32 C27 -0.4(4) . . . . ?
C32 C27 C28 C29 0.9(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_04_250
_database_code_depnum_ccdc_archive 'CCDC 2420440'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H11 N), C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H26 Br2 N2 O2'
_chemical_formula_weight         630.37
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.828(4)
_cell_length_b                   11.110(3)
_cell_length_c                   11.643(4)
_cell_angle_alpha                92.267(11)
_cell_angle_beta                 96.759(13)
_cell_angle_gamma                91.968(11)
_cell_volume                     1388.8(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8034
_cell_measurement_temperature    250.00
_cell_measurement_theta_max      23.672
_cell_measurement_theta_min      2.489
_shelx_estimated_absorpt_T_max   0.645
_shelx_estimated_absorpt_T_min   0.596
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0702 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.9281.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.163
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46246
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.430
_diffrn_ambient_temperature      250.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4229
_reflns_number_total             5618
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5618
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+0.4370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0743
_refine_special_details          
'The ethyl moiety (C12 and C13) was positionally disordered and modeled as split sites (A and B). The refined occupancies for the A and B sites were 0.98 and 0.02, respectively. To help maintain reasonable ADP and bond length values, SIMU, RIGU, and free variable DFIX restraints were applied to the disordered sites.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C12A-C13A = C12B-C13B
 1.3132 with sigma of 0.02
 C9-C12A = C9-C12B = C14-C13A = C14-C13B
 1.46731 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C9 \\sim C12A \\sim C12B \\sim C13A \\sim C13B \\sim C14: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 C12B, C12A, C13B, C13A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C13B)=Sof(H13B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12A(H12A), C13A(H13A),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32), C13B(H13B), C12B(H12B)
6.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72595(3) -0.04463(2) -0.40301(2) 0.04991(11) Uani 1 1 d . . . . .
Br2 Br 0.32520(3) 0.24323(2) -0.30727(2) 0.05332(11) Uani 1 1 d . . . . .
O1 O 0.79878(17) -0.00211(18) -0.14651(15) 0.0554(5) Uani 1 1 d . . . . .
H1 H 0.824057 0.018290 -0.078210 0.083 Uiso 1 1 calc R U . . .
O2 O 0.44980(18) 0.2285(2) -0.06314(16) 0.0606(5) Uani 1 1 d . . . . .
H2 H 0.492503 0.238650 0.000756 0.091 Uiso 1 1 calc R U . . .
N1 N 0.8834(2) 0.0581(2) 0.07548(19) 0.0555(6) Uani 1 1 d . . . . .
C1 C 0.6424(2) 0.0445(2) -0.2948(2) 0.0393(6) Uani 1 1 d . . . . .
C2 C 0.5337(2) 0.0994(2) -0.3329(2) 0.0400(6) Uani 1 1 d . . . . .
H2A H 0.502607 0.094519 -0.411809 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4708(2) 0.1617(2) -0.2543(2) 0.0396(6) Uani 1 1 d . . . . .
C4 C 0.5151(2) 0.1686(2) -0.1371(2) 0.0439(6) Uani 1 1 d . . . . .
C5 C 0.6247(2) 0.1123(2) -0.1012(2) 0.0470(6) Uani 1 1 d . . . . .
H5 H 0.654861 0.115647 -0.022039 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6911(2) 0.0513(2) -0.1786(2) 0.0412(6) Uani 1 1 d . . . . .
C7 C 0.8479(3) -0.0069(3) 0.1590(3) 0.0640(8) Uani 1 1 d . . . . .
H7 H 0.803793 -0.080452 0.138348 0.077 Uiso 1 1 calc R U . . .
C8 C 0.8717(3) 0.0269(3) 0.2748(3) 0.0669(9) Uani 1 1 d . . . . .
H8 H 0.844771 -0.023697 0.330497 0.080 Uiso 1 1 calc R U . . .
C9 C 0.9345(2) 0.1339(3) 0.3095(2) 0.0481(6) Uani 1 1 d D U . . .
C10 C 0.9757(3) 0.2001(3) 0.2232(2) 0.0568(7) Uani 1 1 d . . . . .
H10 H 1.021855 0.272879 0.241773 0.068 Uiso 1 1 calc R U . . .
C11 C 0.9492(3) 0.1593(3) 0.1097(3) 0.0666(8) Uani 1 1 d . . . . .
H11 H 0.979433 0.205797 0.052602 0.080 Uiso 1 1 calc R U . . .
C12A C 0.9519(3) 0.1713(3) 0.4328(2) 0.0538(8) Uani 0.980(5) 1 d D U P A 1
H12A H 0.921885 0.116875 0.483784 0.065 Uiso 0.980(5) 1 calc R U P A 1
C13A C 1.0047(3) 0.2727(3) 0.4798(2) 0.0490(8) Uani 0.980(5) 1 d D U P A 1
H13A H 1.040607 0.324687 0.430116 0.059 Uiso 0.980(5) 1 calc R U P A 1
C14 C 1.0131(2) 0.3127(2) 0.6022(2) 0.0481(6) Uani 1 1 d D U . . .
C15 C 0.9616(3) 0.2470(3) 0.6845(3) 0.0625(8) Uani 1 1 d . . . . .
H15 H 0.920705 0.172078 0.662980 0.075 Uiso 1 1 calc R U . . .
C16 C 0.9696(3) 0.2900(4) 0.7971(3) 0.0788(10) Uani 1 1 d . . . . .
H16 H 0.933993 0.244166 0.851783 0.095 Uiso 1 1 calc R U . . .
C17 C 1.0284(3) 0.3981(4) 0.8313(3) 0.0799(11) Uani 1 1 d . . . . .
H17 H 1.032652 0.426773 0.908740 0.096 Uiso 1 1 calc R U . . .
C18 C 1.0813(3) 0.4648(3) 0.7517(3) 0.0742(10) Uani 1 1 d . . . . .
H18 H 1.123103 0.538921 0.774826 0.089 Uiso 1 1 calc R U . . .
C19 C 1.0729(3) 0.4227(3) 0.6369(3) 0.0584(7) Uani 1 1 d . . . . .
H19 H 1.108003 0.469225 0.582349 0.070 Uiso 1 1 calc R U . . .
N2 N 0.5700(2) 0.2658(2) 0.15182(19) 0.0505(6) Uani 1 1 d . . . . .
C20 C 0.5845(3) 0.1831(3) 0.2319(2) 0.0559(7) Uani 1 1 d . . . . .
H20 H 0.573407 0.101332 0.207507 0.067 Uiso 1 1 calc R U . . .
C21 C 0.6148(3) 0.2109(2) 0.3475(2) 0.0545(7) Uani 1 1 d . . . . .
H21 H 0.624953 0.148727 0.399841 0.065 Uiso 1 1 calc R U . . .
C22 C 0.6305(2) 0.3305(2) 0.3883(2) 0.0441(6) Uani 1 1 d . . . . .
C23 C 0.6154(2) 0.4164(2) 0.3037(2) 0.0500(7) Uani 1 1 d . . . . .
H23 H 0.625530 0.498830 0.325366 0.060 Uiso 1 1 calc R U . . .
C24 C 0.5861(3) 0.3811(3) 0.1899(2) 0.0527(7) Uani 1 1 d . . . . .
H24 H 0.576627 0.441166 0.135266 0.063 Uiso 1 1 calc R U . . .
C25 C 0.6587(3) 0.3610(2) 0.5124(2) 0.0497(7) Uani 1 1 d . . . . .
H25 H 0.670717 0.296410 0.561762 0.060 Uiso 1 1 calc R U . . .
C26 C 0.6687(2) 0.4710(2) 0.5616(2) 0.0489(6) Uani 1 1 d . . . . .
H26 H 0.659876 0.534768 0.510866 0.059 Uiso 1 1 calc R U . . .
C27 C 0.6916(2) 0.5055(2) 0.6846(2) 0.0482(6) Uani 1 1 d . . . . .
C28 C 0.6901(3) 0.4231(3) 0.7715(2) 0.0562(7) Uani 1 1 d . . . . .
H28 H 0.677391 0.340426 0.751418 0.067 Uiso 1 1 calc R U . . .
C29 C 0.7071(3) 0.4612(3) 0.8864(3) 0.0667(8) Uani 1 1 d . . . . .
H29 H 0.705273 0.404344 0.943879 0.080 Uiso 1 1 calc R U . . .
C30 C 0.7266(3) 0.5814(3) 0.9180(3) 0.0720(10) Uani 1 1 d . . . . .
H30 H 0.737335 0.606636 0.996656 0.086 Uiso 1 1 calc R U . . .
C31 C 0.7303(3) 0.6644(3) 0.8342(3) 0.0711(10) Uani 1 1 d . . . . .
H31 H 0.745048 0.746616 0.855443 0.085 Uiso 1 1 calc R U . . .
C32 C 0.7122(3) 0.6272(3) 0.7180(3) 0.0600(8) Uani 1 1 d . . . . .
H32 H 0.713891 0.684707 0.661132 0.072 Uiso 1 1 calc R U . . .
C13B C 0.971(13) 0.226(9) 0.506(7) 0.048(6) Uani 0.020(5) 1 d D U P A 2
H13B H 0.925132 0.158556 0.526722 0.058 Uiso 0.020(5) 1 calc R U P A 2
C12B C 0.987(12) 0.227(8) 0.396(7) 0.049(6) Uani 0.020(5) 1 d D U P A 2
H12B H 1.033947 0.291849 0.371437 0.059 Uiso 0.020(5) 1 calc R U P A 2


_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 1.901(2) . ?
Br2 C3 1.898(2) . ?
O1 H1 0.8300 . ?
O1 C6 1.346(3) . ?
O2 H2 0.8300 . ?
O2 C4 1.348(3) . ?
N1 C7 1.319(4) . ?
N1 C11 1.332(4) . ?
C1 C2 1.379(3) . ?
C1 C6 1.392(3) . ?
C2 H2A 0.9400 . ?
C2 C3 1.381(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.389(4) . ?
C5 H5 0.9400 . ?
C5 C6 1.388(3) . ?
C7 H7 0.9400 . ?
C7 C8 1.378(4) . ?
C8 H8 0.9400 . ?
C8 C9 1.371(4) . ?
C9 C10 1.375(4) . ?
C9 C12A 1.468(4) . ?
C9 C12B 1.47(3) . ?
C10 H10 0.9400 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9400 . ?
C12A H12A 0.9400 . ?
C12A C13A 1.315(4) . ?
C13A H13A 0.9400 . ?
C13A C14 1.467(4) . ?
C14 C15 1.385(4) . ?
C14 C19 1.386(4) . ?
C14 C13B 1.47(3) . ?
C15 H15 0.9400 . ?
C15 C16 1.369(4) . ?
C16 H16 0.9400 . ?
C16 C17 1.361(5) . ?
C17 H17 0.9400 . ?
C17 C18 1.374(5) . ?
C18 H18 0.9400 . ?
C18 C19 1.391(4) . ?
C19 H19 0.9400 . ?
N2 C20 1.335(4) . ?
N2 C24 1.338(3) . ?
C20 H20 0.9400 . ?
C20 C21 1.368(4) . ?
C21 H21 0.9400 . ?
C21 C22 1.391(4) . ?
C22 C23 1.398(4) . ?
C22 C25 1.465(4) . ?
C23 H23 0.9400 . ?
C23 C24 1.364(4) . ?
C24 H24 0.9400 . ?
C25 H25 0.9400 . ?
C25 C26 1.325(4) . ?
C26 H26 0.9400 . ?
C26 C27 1.459(4) . ?
C27 C28 1.391(4) . ?
C27 C32 1.395(4) . ?
C28 H28 0.9400 . ?
C28 C29 1.377(4) . ?
C29 H29 0.9400 . ?
C29 C30 1.373(5) . ?
C30 H30 0.9400 . ?
C30 C31 1.372(5) . ?
C31 H31 0.9400 . ?
C31 C32 1.388(4) . ?
C32 H32 0.9400 . ?
C13B H13B 0.9400 . ?
C13B C12B 1.31(3) . ?
C12B H12B 0.9400 . ?

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 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 115.7(2) . . ?
C2 C1 Br1 119.33(18) . . ?
C2 C1 C6 121.3(2) . . ?
C6 C1 Br1 119.33(19) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 Br2 119.72(18) . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 Br2 119.49(19) . . ?
O2 C4 C3 118.9(2) . . ?
O2 C4 C5 122.8(2) . . ?
C5 C4 C3 118.4(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 H5 119.0 . . ?
O1 C6 C1 118.9(2) . . ?
O1 C6 C5 123.3(2) . . ?
C5 C6 C1 117.8(2) . . ?
N1 C7 H7 118.2 . . ?
N1 C7 C8 123.7(3) . . ?
C8 C7 H7 118.2 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 116.2(3) . . ?
C8 C9 C12A 119.3(3) . . ?
C8 C9 C12B 154(4) . . ?
C10 C9 C12A 124.5(3) . . ?
C10 C9 C12B 90(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
N1 C11 C10 124.2(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C9 C12A H12A 116.4 . . ?
C13A C12A C9 127.1(3) . . ?
C13A C12A H12A 116.4 . . ?
C12A C13A H13A 116.8 . . ?
C12A C13A C14 126.4(3) . . ?
C14 C13A H13A 116.8 . . ?
C15 C14 C13A 123.1(3) . . ?
C15 C14 C19 118.2(3) . . ?
C15 C14 C13B 95(5) . . ?
C19 C14 C13A 118.6(3) . . ?
C19 C14 C13B 147(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.5(3) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.5(3) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C20 N2 C24 116.5(2) . . ?
N2 C20 H20 118.3 . . ?
N2 C20 C21 123.5(3) . . ?
C21 C20 H20 118.3 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 115.5(2) . . ?
C21 C22 C25 120.8(2) . . ?
C23 C22 C25 123.7(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
N2 C24 C23 123.6(3) . . ?
N2 C24 H24 118.2 . . ?
C23 C24 H24 118.2 . . ?
C22 C25 H25 116.9 . . ?
C26 C25 C22 126.1(3) . . ?
C26 C25 H25 116.9 . . ?
C25 C26 H26 116.0 . . ?
C25 C26 C27 128.0(3) . . ?
C27 C26 H26 116.0 . . ?
C28 C27 C26 123.2(2) . . ?
C28 C27 C32 117.8(3) . . ?
C32 C27 C26 118.9(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.8(3) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.7(3) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.1(3) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 H32 119.6 . . ?
C31 C32 C27 120.9(3) . . ?
C31 C32 H32 119.6 . . ?
C14 C13B H13B 114.7 . . ?
C12B C13B C14 131(6) . . ?
C12B C13B H13B 114.7 . . ?
C9 C12B H12B 118.1 . . ?
C13B C12B C9 124(5) . . ?
C13B C12B H12B 118.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.86 2.689(3) 177.8 . yes
O2 H2 N2 0.83 1.87 2.691(3) 172.8 . yes

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
Br1 C1 C2 C3 178.33(18) . . . . ?
Br1 C1 C6 O1 2.3(3) . . . . ?
Br1 C1 C6 C5 -177.04(19) . . . . ?
Br2 C3 C4 O2 3.1(3) . . . . ?
Br2 C3 C4 C5 -177.4(2) . . . . ?
O2 C4 C5 C6 -179.8(2) . . . . ?
N1 C7 C8 C9 0.7(5) . . . . ?
C1 C2 C3 Br2 177.27(18) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C1 C6 O1 -178.8(2) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C2 C3 C4 O2 -178.9(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 O1 178.7(2) . . . . ?
C4 C5 C6 C1 -2.0(4) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C7 N1 C11 C10 -3.0(5) . . . . ?
C7 C8 C9 C10 -2.9(5) . . . . ?
C7 C8 C9 C12A 176.2(3) . . . . ?
C7 C8 C9 C12B 176(12) . . . . ?
C8 C9 C10 C11 2.2(4) . . . . ?
C8 C9 C12A C13A -176.9(3) . . . . ?
C8 C9 C12B C13B -5(24) . . . . ?
C9 C10 C11 N1 0.8(5) . . . . ?
C9 C12A C13A C14 175.2(3) . . . . ?
C10 C9 C12A C13A 2.1(5) . . . . ?
C10 C9 C12B C13B 174(14) . . . . ?
C11 N1 C7 C8 2.3(5) . . . . ?
C12A C9 C10 C11 -176.8(3) . . . . ?
C12A C13A C14 C15 -1.8(5) . . . . ?
C12A C13A C14 C19 179.8(3) . . . . ?
C13A C14 C15 C16 -178.4(3) . . . . ?
C13A C14 C19 C18 179.0(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C14 C13B C12B C9 -178(11) . . . . ?
C15 C14 C19 C18 0.5(4) . . . . ?
C15 C14 C13B C12B -179(16) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C16 C17 C18 C19 1.0(5) . . . . ?
C17 C18 C19 C14 -1.0(5) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C19 C14 C13B C12B 4(25) . . . . ?
N2 C20 C21 C22 0.9(5) . . . . ?
C20 N2 C24 C23 -0.2(4) . . . . ?
C20 C21 C22 C23 -1.0(4) . . . . ?
C20 C21 C22 C25 177.9(3) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C21 C22 C25 C26 -176.0(3) . . . . ?
C22 C23 C24 N2 0.1(4) . . . . ?
C22 C25 C26 C27 177.4(3) . . . . ?
C23 C22 C25 C26 2.8(4) . . . . ?
C24 N2 C20 C21 -0.3(4) . . . . ?
C25 C22 C23 C24 -178.3(3) . . . . ?
C25 C26 C27 C28 -9.0(5) . . . . ?
C25 C26 C27 C32 173.2(3) . . . . ?
C26 C27 C28 C29 -177.1(3) . . . . ?
C26 C27 C32 C31 177.8(3) . . . . ?
C27 C28 C29 C30 -0.4(5) . . . . ?
C28 C27 C32 C31 -0.2(4) . . . . ?
C28 C29 C30 C31 -0.5(5) . . . . ?
C29 C30 C31 C32 1.1(5) . . . . ?
C30 C31 C32 C27 -0.8(5) . . . . ?
C32 C27 C28 C29 0.7(4) . . . . ?
C13B C14 C15 C16 -178(6) . . . . ?
C13B C14 C19 C18 177(11) . . . . ?
C12B C9 C10 C11 -177(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_08_210
_database_code_depnum_ccdc_archive 'CCDC 2420454'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H10.28 N), C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H24.53 Br2 N2 O2'
_chemical_formula_weight         628.89
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8319(5)
_cell_length_b                   11.0319(5)
_cell_length_c                   11.6933(6)
_cell_angle_alpha                91.7910(10)
_cell_angle_beta                 97.468(2)
_cell_angle_gamma                91.8610(10)
_cell_volume                     1383.84(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    210.00
_cell_measurement_theta_max      26.746
_cell_measurement_theta_min      2.600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.961
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.8636.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             633
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.155
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            43206
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      210.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4532
_reflns_number_total             5548
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5548
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+0.7023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0715
_refine_special_details          
'In this structure, there was a mixture of 4-phenylethynyl)pyridine (A sites) and 4-stilbazole (B-sites). At this temperature, the refined occupancies of the A and B sites for molecules containing nitrogen atom N1 or N2 were 0.37:0.63 and 0.36:0.64, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, SIMU, RIGU, free variable DFIX and AFIX restraints and constraints were applied where necessary.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C12A-C13A = C25A-C26A
 1.16685 with sigma of 0.02
 C12B-C13B = C25B-C26B
 1.34918 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25A \\sim C25B \\sim C26A \\sim C26B: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.02 within 2A
C9 \\sim C12B \\sim C12A \\sim C13A \\sim C13B \\sim C14A \\sim C15A \\sim C16A
\\sim C17A \\sim C18A \\sim C19A \\sim C14B \\sim C15B \\sim C17B \\sim C16B
\\sim C18B \\sim C19B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C25B, C25A, C26A, C26B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 C9, C12B, C12A, C13A, C13B, C14A, C15A, C16A, C17A, C18A, C19A, C14B, C15B,
 C17B, C16B, C18B, C19B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C19B)=Sof(H19B)=
 Sof(C18B)=Sof(H18B)=Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=
 Sof(H15B)=1-FVAR(1)
 Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=FVAR(1)
 Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=1-FVAR(2)
 Sof(C25A)=Sof(C26A)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C19A(H19A), C18A(H18A),
 C17A(H17A), C16A(H16A), C15A(H15A), C12B(H12B), C13B(H13B), C19B(H19B),
 C18B(H18B), C17B(H17B), C16B(H16B), C15B(H15B), C20(H20), C21(H21), C23(H23),
 C24(H24), C25B(H25B), C26B(H26B), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32)
6.b Fitted hexagon refined as free rotating group:
 C14A(C19A,C18A,C17A,C16A,C15A), C14B(C19B,C18B,C17B,C16B,C15B)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72863(2) -0.04212(2) -0.40240(2) 0.04836(10) Uani 1 1 d . . . . .
Br2 Br 0.32470(2) 0.24382(2) -0.31316(2) 0.04987(11) Uani 1 1 d . . . . .
O1 O 0.79742(15) -0.00627(16) -0.14544(13) 0.0502(4) Uani 1 1 d . . . . .
H1 H 0.820384 0.010327 -0.076053 0.075 Uiso 1 1 calc R U . . .
O2 O 0.44570(16) 0.22336(17) -0.06767(15) 0.0559(5) Uani 1 1 d . . . . .
H2 H 0.487017 0.230651 -0.002728 0.084 Uiso 1 1 calc R U . . .
N1 N 0.88074(19) 0.0500(2) 0.07703(17) 0.0515(5) Uani 1 1 d . . . . .
C1 C 0.6432(2) 0.04440(19) -0.29595(18) 0.0374(5) Uani 1 1 d . . . . .
C2 C 0.5346(2) 0.10054(18) -0.33530(18) 0.0381(5) Uani 1 1 d . . . . .
H2A H 0.504660 0.097631 -0.414513 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4699(2) 0.16106(18) -0.25805(19) 0.0374(5) Uani 1 1 d . . . . .
C4 C 0.5120(2) 0.1649(2) -0.14033(19) 0.0403(5) Uani 1 1 d . . . . .
C5 C 0.6217(2) 0.1077(2) -0.10274(19) 0.0424(5) Uani 1 1 d . . . . .
H5 H 0.650631 0.109170 -0.023335 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6900(2) 0.04844(19) -0.17895(18) 0.0388(5) Uani 1 1 d . . . . .
C7 C 0.8454(3) -0.0124(3) 0.1629(2) 0.0578(7) Uani 1 1 d . . . . .
H7 H 0.800307 -0.086349 0.145084 0.069 Uiso 1 1 calc R U . . .
C8 C 0.8714(3) 0.0256(2) 0.2771(2) 0.0588(7) Uani 1 1 d . . . . .
H8 H 0.845191 -0.022597 0.334913 0.071 Uiso 1 1 calc R U . . .
C9 C 0.9359(2) 0.1344(2) 0.3068(2) 0.0458(5) Uani 1 1 d . U . . .
C10 C 0.9757(2) 0.1977(3) 0.2178(2) 0.0554(6) Uani 1 1 d . . . . .
H10 H 1.022200 0.271144 0.233116 0.066 Uiso 1 1 calc R U . . .
C11 C 0.9468(3) 0.1524(3) 0.1065(2) 0.0599(7) Uani 1 1 d . . . . .
H11 H 0.975619 0.196709 0.047285 0.072 Uiso 1 1 calc R U . . .
C12A C 0.9700(16) 0.1944(15) 0.4159(13) 0.050(2) Uani 0.374(13) 1 d D U P A 1
C13A C 0.9851(12) 0.2440(12) 0.5058(10) 0.049(2) Uani 0.374(13) 1 d D U P A 1
C14A C 1.0070(15) 0.3074(11) 0.6095(6) 0.0479(17) Uani 0.374(13) 1 d G U P A 1
C19A C 1.0696(14) 0.4199(11) 0.6147(7) 0.0517(18) Uani 0.374(13) 1 d G U P A 1
H19A H 1.097866 0.450403 0.548188 0.062 Uiso 0.374(13) 1 calc R U P A 1
C18A C 1.0904(10) 0.4872(8) 0.7183(10) 0.0536(19) Uani 0.374(13) 1 d G U P A 1
H18A H 1.132671 0.563297 0.721839 0.064 Uiso 0.374(13) 1 calc R U P A 1
C17A C 1.0486(9) 0.4421(10) 0.8167(6) 0.0532(19) Uani 0.374(13) 1 d G U P A 1
H17A H 1.062617 0.487674 0.886723 0.064 Uiso 0.374(13) 1 calc R U P A 1
C16A C 0.9860(10) 0.3297(10) 0.8114(7) 0.0576(19) Uani 0.374(13) 1 d G U P A 1
H16A H 0.957757 0.299154 0.877956 0.069 Uiso 0.374(13) 1 calc R U P A 1
C15A C 0.9653(12) 0.2623(8) 0.7078(9) 0.0555(18) Uani 0.374(13) 1 d G U P A 1
H15A H 0.922952 0.186257 0.704305 0.067 Uiso 0.374(13) 1 calc R U P A 1
C12B C 0.9502(9) 0.1687(8) 0.4317(7) 0.0451(15) Uani 0.626(13) 1 d D U P A 2
H12B H 0.918419 0.114322 0.481858 0.054 Uiso 0.626(13) 1 calc R U P A 2
C13B C 1.0058(6) 0.2729(6) 0.4771(6) 0.0430(12) Uani 0.626(13) 1 d D U P A 2
H13B H 1.042108 0.324042 0.427009 0.052 Uiso 0.626(13) 1 calc R U P A 2
C14B C 1.0148(8) 0.3147(6) 0.6024(3) 0.0473(12) Uani 0.626(13) 1 d G U P A 2
C19B C 1.0757(7) 0.4247(6) 0.6387(5) 0.0469(11) Uani 0.626(13) 1 d G U P A 2
H19B H 1.112620 0.471812 0.585756 0.056 Uiso 0.626(13) 1 calc R U P A 2
C18B C 1.0821(6) 0.4651(5) 0.7532(5) 0.0518(13) Uani 0.626(13) 1 d G U P A 2
H18B H 1.123280 0.539512 0.777659 0.062 Uiso 0.626(13) 1 calc R U P A 2
C17B C 1.0275(5) 0.3954(7) 0.8314(3) 0.0558(15) Uani 0.626(13) 1 d G U P A 2
H17B H 1.031802 0.422749 0.908817 0.067 Uiso 0.626(13) 1 calc R U P A 2
C16B C 0.9666(5) 0.2854(7) 0.7952(4) 0.0641(14) Uani 0.626(13) 1 d G U P A 2
H16B H 0.929663 0.238285 0.848073 0.077 Uiso 0.626(13) 1 calc R U P A 2
C15B C 0.9602(7) 0.2450(5) 0.6807(5) 0.0579(13) Uani 0.626(13) 1 d G U P A 2
H15B H 0.919003 0.170582 0.656171 0.069 Uiso 0.626(13) 1 calc R U P A 2
N2 N 0.56607(19) 0.26128(19) 0.14768(17) 0.0481(5) Uani 1 1 d . . . . .
C20 C 0.5830(2) 0.1796(2) 0.2299(2) 0.0504(6) Uani 1 1 d . . . . .
H20 H 0.572632 0.096842 0.207830 0.060 Uiso 1 1 calc R U . . .
C21 C 0.6147(2) 0.2103(2) 0.3448(2) 0.0510(6) Uani 1 1 d . . . . .
H21 H 0.627188 0.148996 0.398808 0.061 Uiso 1 1 calc R U . . .
C22 C 0.6285(2) 0.3312(2) 0.3818(2) 0.0458(5) Uani 1 1 d . . . . .
C23 C 0.6104(2) 0.4162(2) 0.2956(2) 0.0516(6) Uani 1 1 d . . . . .
H23 H 0.618838 0.499658 0.315102 0.062 Uiso 1 1 calc R U . . .
C24 C 0.5803(2) 0.3777(2) 0.1826(2) 0.0513(6) Uani 1 1 d . . . . .
H24 H 0.568907 0.436811 0.126429 0.062 Uiso 1 1 calc R U . . .
C25A C 0.657(2) 0.3866(18) 0.4894(15) 0.047(3) Uani 0.36(3) 1 d D U P B 1
C26A C 0.6763(15) 0.433(2) 0.5821(13) 0.049(3) Uani 0.36(3) 1 d D U P B 1
C25B C 0.6577(11) 0.3560(8) 0.5107(8) 0.0398(15) Uani 0.64(3) 1 d D U P B 2
H25B H 0.669844 0.290443 0.559938 0.048 Uiso 0.64(3) 1 calc R U P B 2
C26B C 0.6667(8) 0.4710(8) 0.5565(8) 0.0399(14) Uani 0.64(3) 1 d D U P B 2
H26B H 0.656415 0.535963 0.506432 0.048 Uiso 0.64(3) 1 calc R U P B 2
C27 C 0.6928(2) 0.4986(2) 0.6856(2) 0.0496(6) Uani 1 1 d . . . . .
C28 C 0.6914(3) 0.4199(3) 0.7751(2) 0.0590(7) Uani 1 1 d . . . . .
H28 H 0.678386 0.336198 0.758463 0.071 Uiso 1 1 calc R U . . .
C29 C 0.7089(3) 0.4621(3) 0.8881(3) 0.0676(8) Uani 1 1 d . . . . .
H29 H 0.707167 0.407441 0.948003 0.081 Uiso 1 1 calc R U . . .
C30 C 0.7289(3) 0.5847(3) 0.9138(3) 0.0695(9) Uani 1 1 d . . . . .
H30 H 0.740589 0.613603 0.991012 0.083 Uiso 1 1 calc R U . . .
C31 C 0.7318(3) 0.6642(3) 0.8262(3) 0.0655(8) Uani 1 1 d . . . . .
H31 H 0.746381 0.747640 0.843658 0.079 Uiso 1 1 calc R U . . .
C32 C 0.7133(2) 0.6224(2) 0.7123(2) 0.0566(7) Uani 1 1 d . . . . .
H32 H 0.714498 0.677451 0.652734 0.068 Uiso 1 1 calc R U . . .


_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(2) . ?
Br2 C3 1.895(2) . ?
O1 H1 0.8300 . ?
O1 C6 1.347(3) . ?
O2 H2 0.8300 . ?
O2 C4 1.345(3) . ?
N1 C7 1.325(3) . ?
N1 C11 1.329(4) . ?
C1 C2 1.380(3) . ?
C1 C6 1.395(3) . ?
C2 H2A 0.9400 . ?
C2 C3 1.382(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.390(3) . ?
C5 H5 0.9400 . ?
C5 C6 1.391(3) . ?
C7 H7 0.9400 . ?
C7 C8 1.377(3) . ?
C8 H8 0.9400 . ?
C8 C9 1.380(4) . ?
C9 C10 1.378(4) . ?
C9 C12A 1.418(16) . ?
C9 C12B 1.485(8) . ?
C10 H10 0.9400 . ?
C10 C11 1.372(4) . ?
C11 H11 0.9400 . ?
C12A C13A 1.16(2) . ?
C13A C14A 1.370(12) . ?
C14A C19A 1.3900 . ?
C14A C15A 1.3900 . ?
C19A H19A 0.9400 . ?
C19A C18A 1.3900 . ?
C18A H18A 0.9400 . ?
C18A C17A 1.3900 . ?
C17A H17A 0.9400 . ?
C17A C16A 1.3900 . ?
C16A H16A 0.9400 . ?
C16A C15A 1.3900 . ?
C15A H15A 0.9400 . ?
C12B H12B 0.9400 . ?
C12B C13B 1.341(11) . ?
C13B H13B 0.9400 . ?
C13B C14B 1.512(7) . ?
C14B C19B 1.3900 . ?
C14B C15B 1.3900 . ?
C19B H19B 0.9400 . ?
C19B C18B 1.3900 . ?
C18B H18B 0.9400 . ?
C18B C17B 1.3900 . ?
C17B H17B 0.9400 . ?
C17B C16B 1.3900 . ?
C16B H16B 0.9400 . ?
C16B C15B 1.3900 . ?
C15B H15B 0.9400 . ?
N2 C20 1.338(3) . ?
N2 C24 1.333(3) . ?
C20 H20 0.9400 . ?
C20 C21 1.372(3) . ?
C21 H21 0.9400 . ?
C21 C22 1.387(3) . ?
C22 C23 1.397(4) . ?
C22 C25A 1.376(16) . ?
C22 C25B 1.514(9) . ?
C23 H23 0.9400 . ?
C23 C24 1.369(4) . ?
C24 H24 0.9400 . ?
C25A C26A 1.17(2) . ?
C26A C27 1.379(12) . ?
C25B H25B 0.9400 . ?
C25B C26B 1.357(13) . ?
C26B H26B 0.9400 . ?
C26B C27 1.519(9) . ?
C27 C28 1.382(4) . ?
C27 C32 1.395(4) . ?
C28 H28 0.9400 . ?
C28 C29 1.375(4) . ?
C29 H29 0.9400 . ?
C29 C30 1.380(5) . ?
C30 H30 0.9400 . ?
C30 C31 1.372(5) . ?
C31 H31 0.9400 . ?
C31 C32 1.383(4) . ?
C32 H32 0.9400 . ?

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 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 116.3(2) . . ?
C2 C1 Br1 119.44(15) . . ?
C2 C1 C6 121.1(2) . . ?
C6 C1 Br1 119.46(16) . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.88(19) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 Br2 119.72(16) . . ?
C2 C3 C4 120.80(19) . . ?
C4 C3 Br2 119.45(16) . . ?
O2 C4 C3 119.1(2) . . ?
O2 C4 C5 122.7(2) . . ?
C5 C4 C3 118.3(2) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.1(2) . . ?
C6 C5 H5 119.0 . . ?
O1 C6 C1 118.64(19) . . ?
O1 C6 C5 123.48(19) . . ?
C5 C6 C1 117.9(2) . . ?
N1 C7 H7 118.4 . . ?
N1 C7 C8 123.2(3) . . ?
C8 C7 H7 118.4 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C12A 130.8(7) . . ?
C8 C9 C12B 114.7(4) . . ?
C10 C9 C8 116.6(2) . . ?
C10 C9 C12A 112.6(7) . . ?
C10 C9 C12B 128.7(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
N1 C11 C10 124.3(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C13A C12A C9 173.0(19) . . ?
C12A C13A C14A 176.7(18) . . ?
C13A C14A C19A 118.9(8) . . ?
C13A C14A C15A 121.0(8) . . ?
C19A C14A C15A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C17A C18A C19A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C9 C12B H12B 118.1 . . ?
C13B C12B C9 123.8(8) . . ?
C13B C12B H12B 118.1 . . ?
C12B C13B H13B 117.3 . . ?
C12B C13B C14B 125.3(7) . . ?
C14B C13B H13B 117.3 . . ?
C19B C14B C13B 119.6(4) . . ?
C19B C14B C15B 120.0 . . ?
C15B C14B C13B 120.4(4) . . ?
C14B C19B H19B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C24 N2 C20 116.5(2) . . ?
N2 C20 H20 118.3 . . ?
N2 C20 C21 123.4(2) . . ?
C21 C20 H20 118.3 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 116.0(2) . . ?
C21 C22 C25B 116.4(4) . . ?
C23 C22 C25B 127.6(4) . . ?
C25A C22 C21 132.4(9) . . ?
C25A C22 C23 111.6(9) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.1 . . ?
N2 C24 C23 123.9(2) . . ?
N2 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
C26A C25A C22 177(3) . . ?
C25A C26A C27 174(3) . . ?
C22 C25B H25B 119.4 . . ?
C26B C25B C22 121.2(11) . . ?
C26B C25B H25B 119.4 . . ?
C25B C26B H26B 118.8 . . ?
C25B C26B C27 122.5(12) . . ?
C27 C26B H26B 118.8 . . ?
C26A C27 C28 109.2(10) . . ?
C26A C27 C32 132.2(10) . . ?
C28 C27 C26B 128.8(4) . . ?
C28 C27 C32 118.5(2) . . ?
C32 C27 C26B 112.6(4) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(3) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.3(3) . . ?
C32 C31 H31 119.8 . . ?
C27 C32 H32 119.9 . . ?
C31 C32 C27 120.2(3) . . ?
C31 C32 H32 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.86 2.687(2) 176.7 . yes
O2 H2 N2 0.83 1.87 2.695(3) 172.9 . yes

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
Br1 C1 C2 C3 178.29(16) . . . . ?
Br1 C1 C6 O1 2.2(3) . . . . ?
Br1 C1 C6 C5 -176.95(17) . . . . ?
Br2 C3 C4 O2 2.7(3) . . . . ?
Br2 C3 C4 C5 -177.31(17) . . . . ?
O2 C4 C5 C6 -179.4(2) . . . . ?
N1 C7 C8 C9 0.9(5) . . . . ?
C1 C2 C3 Br2 177.34(16) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C1 C6 O1 -179.0(2) . . . . ?
C2 C1 C6 C5 1.9(3) . . . . ?
C2 C3 C4 O2 -179.2(2) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 O1 179.0(2) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C7 N1 C11 C10 -2.3(4) . . . . ?
C7 C8 C9 C10 -2.6(4) . . . . ?
C7 C8 C9 C12A 177.7(10) . . . . ?
C7 C8 C9 C12B 176.0(5) . . . . ?
C8 C9 C10 C11 1.9(4) . . . . ?
C8 C9 C12B C13B -177.5(8) . . . . ?
C9 C10 C11 N1 0.6(4) . . . . ?
C9 C12B C13B C14B 175.8(7) . . . . ?
C10 C9 C12B C13B 0.9(13) . . . . ?
C11 N1 C7 C8 1.6(4) . . . . ?
C12A C9 C10 C11 -178.3(8) . . . . ?
C13A C14A C19A C18A 178.5(14) . . . . ?
C13A C14A C15A C16A -178.4(14) . . . . ?
C14A C19A C18A C17A 0.0 . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?
C19A C18A C17A C16A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C17A C16A C15A C14A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C12B C9 C10 C11 -176.5(6) . . . . ?
C12B C13B C14B C19B 179.7(8) . . . . ?
C12B C13B C14B C15B -1.7(11) . . . . ?
C13B C14B C19B C18B 178.6(7) . . . . ?
C13B C14B C15B C16B -178.6(7) . . . . ?
C14B C19B C18B C17B 0.0 . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C19B C18B C17B C16B 0.0 . . . . ?
C18B C17B C16B C15B 0.0 . . . . ?
C17B C16B C15B C14B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
N2 C20 C21 C22 1.3(4) . . . . ?
C20 N2 C24 C23 -0.1(4) . . . . ?
C20 C21 C22 C23 -1.1(4) . . . . ?
C20 C21 C22 C25A 179.0(14) . . . . ?
C20 C21 C22 C25B 177.2(6) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C21 C22 C25B C26B -176.6(9) . . . . ?
C22 C23 C24 N2 0.2(4) . . . . ?
C22 C25B C26B C27 178.5(6) . . . . ?
C23 C22 C25B C26B 1.5(15) . . . . ?
C24 N2 C20 C21 -0.7(4) . . . . ?
C25A C22 C23 C24 -179.7(11) . . . . ?
C26A C27 C28 C29 178.5(8) . . . . ?
C26A C27 C32 C31 -177.4(10) . . . . ?
C25B C22 C23 C24 -177.8(6) . . . . ?
C25B C26B C27 C28 -11.4(12) . . . . ?
C25B C26B C27 C32 172.6(9) . . . . ?
C26B C27 C28 C29 -175.3(5) . . . . ?
C26B C27 C32 C31 176.5(4) . . . . ?
C27 C28 C29 C30 -0.4(4) . . . . ?
C28 C27 C32 C31 0.0(4) . . . . ?
C28 C29 C30 C31 -0.2(4) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
C30 C31 C32 C27 -0.6(4) . . . . ?
C32 C27 C28 C29 0.5(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gro23_08_270
_database_code_depnum_ccdc_archive 'CCDC 2420451'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;University of Iowa
United States of America
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10.20 N, C13 H10.32 N, C6 H4 Br2 O2'
_chemical_formula_sum            'C32 H24.52 Br2 N2 O2'
_chemical_formula_weight         628.87
_chemical_melting_point          ?
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9159(6)
_cell_length_b                   11.0588(6)
_cell_length_c                   11.7098(7)
_cell_angle_alpha                92.098(2)
_cell_angle_beta                 97.391(2)
_cell_angle_gamma                91.784(2)
_cell_volume                     1399.97(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9211
_cell_measurement_temperature    270.00
_cell_measurement_theta_max      23.815
_cell_measurement_theta_min      2.587
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.927
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0810 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.8623.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             633
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.155
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            41458
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.401
_diffrn_ambient_temperature      270.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4037
_reflns_number_total             5222
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5222
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+0.7995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          
'In this structure, there was a mixture of 4-phenylethynyl)pyridine (A sites) and 4-stilbazole (B-sites). At this temperature, the refined occupancies of the A and B sites for molecules containing nitrogen atom N1 or N2 were 0.40:0.60 and 0.34:0.66, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, SIMU, RIGU, free variable DFIX and AFIX restraints and constraints were applied where necessary.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C12A-C13A = C25A-C26A
 1.13875 with sigma of 0.02
 C12B-C13B = C25B-C26B
 1.34832 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25A \\sim C25B \\sim C26A \\sim C26B: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.02 within 2A
C9 \\sim C12B \\sim C12A \\sim C13A \\sim C13B \\sim C14A \\sim C15A \\sim C16A
\\sim C17A \\sim C18A \\sim C19A \\sim C14B \\sim C15B \\sim C17B \\sim C16B
\\sim C18B \\sim C19B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C25B, C25A, C26A, C26B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
 C9, C12B, C12A, C13A, C13B, C14A, C15A, C16A, C17A, C18A, C19A, C14B, C15B,
 C17B, C16B, C18B, C19B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C19B)=Sof(H19B)=
 Sof(C18B)=Sof(H18B)=Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=
 Sof(H15B)=1-FVAR(1)
 Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=FVAR(1)
 Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=1-FVAR(2)
 Sof(C25A)=Sof(C26A)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C19A(H19A), C18A(H18A),
 C17A(H17A), C16A(H16A), C15A(H15A), C12B(H12B), C13B(H13B), C19B(H19B),
 C18B(H18B), C17B(H17B), C16B(H16B), C15B(H15B), C20(H20), C21(H21), C23(H23),
 C24(H24), C25B(H25B), C26B(H26B), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32)
6.b Fitted hexagon refined as free rotating group:
 C14A(C19A,C18A,C17A,C16A,C15A), C14B(C19B,C18B,C17B,C16B,C15B)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72760(3) -0.04153(3) -0.40241(2) 0.06431(14) Uani 1 1 d . . . . .
Br2 Br 0.32636(3) 0.24266(3) -0.31145(3) 0.06661(14) Uani 1 1 d . . . . .
O1 O 0.79586(19) -0.0056(2) -0.14579(16) 0.0672(6) Uani 1 1 d . . . . .
H1 H 0.817195 0.008773 -0.074977 0.101 Uiso 1 1 calc R U . . .
O2 O 0.44711(19) 0.2234(2) -0.06680(18) 0.0740(6) Uani 1 1 d . . . . .
H2 H 0.489080 0.231861 -0.001485 0.111 Uiso 1 1 calc R U . . .
N1 N 0.8792(2) 0.0499(3) 0.0771(2) 0.0667(7) Uani 1 1 d . . . . .
C1 C 0.6428(2) 0.0448(2) -0.2956(2) 0.0488(6) Uani 1 1 d . . . . .
C2 C 0.5350(2) 0.1005(2) -0.3344(2) 0.0489(6) Uani 1 1 d . . . . .
H2A H 0.504989 0.097420 -0.414349 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4706(2) 0.1610(2) -0.2569(2) 0.0489(6) Uani 1 1 d . . . . .
C4 C 0.5131(2) 0.1647(2) -0.1400(2) 0.0523(6) Uani 1 1 d . . . . .
C5 C 0.6216(3) 0.1079(2) -0.1031(2) 0.0557(7) Uani 1 1 d . . . . .
H5 H 0.650727 0.109620 -0.022982 0.067 Uiso 1 1 calc R U . . .
C6 C 0.6891(2) 0.0487(2) -0.1791(2) 0.0509(6) Uani 1 1 d . . . . .
C7 C 0.8445(3) -0.0109(3) 0.1626(3) 0.0760(9) Uani 1 1 d . . . . .
H7 H 0.798622 -0.085160 0.144852 0.091 Uiso 1 1 calc R U . . .
C8 C 0.8712(3) 0.0274(3) 0.2764(3) 0.0775(9) Uani 1 1 d . . . . .
H8 H 0.844911 -0.020707 0.334869 0.093 Uiso 1 1 calc R U . . .
C9 C 0.9356(3) 0.1350(3) 0.3059(2) 0.0608(7) Uani 1 1 d . U . . .
C10 C 0.9746(3) 0.1974(3) 0.2173(3) 0.0732(9) Uani 1 1 d . . . . .
H10 H 1.021370 0.271430 0.232578 0.088 Uiso 1 1 calc R U . . .
C11 C 0.9450(3) 0.1517(4) 0.1060(3) 0.0798(10) Uani 1 1 d . . . . .
H11 H 0.973575 0.195912 0.045991 0.096 Uiso 1 1 calc R U . . .
C12A C 0.9699(17) 0.1972(16) 0.4146(14) 0.066(3) Uani 0.399(13) 1 d D U P A 1
C13A C 0.9841(13) 0.2426(13) 0.5043(11) 0.064(2) Uani 0.399(13) 1 d D U P A 1
C14A C 1.0080(15) 0.3057(11) 0.6088(7) 0.0631(18) Uani 0.399(13) 1 d G U P A 1
C19A C 1.0692(14) 0.4182(11) 0.6133(7) 0.069(2) Uani 0.399(13) 1 d G U P A 1
H19A H 1.096665 0.448634 0.545766 0.083 Uiso 0.399(13) 1 calc R U P A 1
C18A C 1.0901(10) 0.4863(8) 0.7165(10) 0.070(2) Uani 0.399(13) 1 d G U P A 1
H18A H 1.131862 0.563211 0.719585 0.084 Uiso 0.399(13) 1 calc R U P A 1
C17A C 1.0498(10) 0.4418(11) 0.8153(7) 0.071(2) Uani 0.399(13) 1 d G U P A 1
H17A H 1.064104 0.488317 0.885883 0.085 Uiso 0.399(13) 1 calc R U P A 1
C16A C 0.9887(10) 0.3293(11) 0.8108(7) 0.075(2) Uani 0.399(13) 1 d G U P A 1
H16A H 0.961150 0.298846 0.878363 0.090 Uiso 0.399(13) 1 calc R U P A 1
C15A C 0.9678(12) 0.2612(9) 0.7076(10) 0.0735(19) Uani 0.399(13) 1 d G U P A 1
H15A H 0.925952 0.184267 0.704545 0.088 Uiso 0.399(13) 1 calc R U P A 1
C12B C 0.9495(10) 0.1687(9) 0.4317(8) 0.0599(18) Uani 0.601(13) 1 d D U P A 2
H12B H 0.916680 0.114389 0.482015 0.072 Uiso 0.601(13) 1 calc R U P A 2
C13B C 1.0059(8) 0.2717(8) 0.4768(7) 0.0600(16) Uani 0.601(13) 1 d D U P A 2
H13B H 1.043627 0.322457 0.426534 0.072 Uiso 0.601(13) 1 calc R U P A 2
C14B C 1.0140(10) 0.3135(7) 0.6025(4) 0.0620(14) Uani 0.601(13) 1 d G U P A 2
C19B C 1.0757(8) 0.4226(7) 0.6396(5) 0.0643(14) Uani 0.601(13) 1 d G U P A 2
H19B H 1.113057 0.469981 0.586525 0.077 Uiso 0.601(13) 1 calc R U P A 2
C18B C 1.0826(6) 0.4624(6) 0.7543(6) 0.0682(16) Uani 0.601(13) 1 d G U P A 2
H18B H 1.124766 0.536895 0.779654 0.082 Uiso 0.601(13) 1 calc R U P A 2
C17B C 1.0279(6) 0.3930(9) 0.8319(4) 0.0727(18) Uani 0.601(13) 1 d G U P A 2
H17B H 1.032704 0.420211 0.910320 0.087 Uiso 0.601(13) 1 calc R U P A 2
C16B C 0.9663(7) 0.2840(8) 0.7948(5) 0.0827(17) Uani 0.601(13) 1 d G U P A 2
H16B H 0.928932 0.236610 0.847857 0.099 Uiso 0.601(13) 1 calc R U P A 2
C15B C 0.9594(8) 0.2442(6) 0.6801(6) 0.0764(16) Uani 0.601(13) 1 d G U P A 2
H15B H 0.917222 0.169693 0.654728 0.092 Uiso 0.601(13) 1 calc R U P A 2
N2 N 0.5661(2) 0.2618(2) 0.1486(2) 0.0631(6) Uani 1 1 d . . . . .
C20 C 0.5832(3) 0.1813(3) 0.2309(3) 0.0668(8) Uani 1 1 d . . . . .
H20 H 0.573100 0.097770 0.208656 0.080 Uiso 1 1 calc R U . . .
C21 C 0.6143(3) 0.2120(3) 0.3450(3) 0.0682(8) Uani 1 1 d . . . . .
H21 H 0.626273 0.150417 0.399336 0.082 Uiso 1 1 calc R U . . .
C22 C 0.6284(3) 0.3324(3) 0.3821(2) 0.0581(7) Uani 1 1 d . . . . .
C23 C 0.6102(3) 0.4164(3) 0.2963(3) 0.0669(8) Uani 1 1 d . . . . .
H23 H 0.618628 0.500586 0.316009 0.080 Uiso 1 1 calc R U . . .
C24 C 0.5801(3) 0.3777(3) 0.1839(3) 0.0685(8) Uani 1 1 d . . . . .
H24 H 0.568416 0.437163 0.127424 0.082 Uiso 1 1 calc R U . . .
C25A C 0.654(2) 0.391(2) 0.4877(17) 0.059(4) Uani 0.34(3) 1 d D U P B 1
C26A C 0.677(2) 0.430(2) 0.5795(14) 0.061(3) Uani 0.34(3) 1 d D U P B 1
C25B C 0.6589(12) 0.3568(9) 0.5108(9) 0.0529(18) Uani 0.66(3) 1 d D U P B 2
H25B H 0.672713 0.290485 0.559605 0.064 Uiso 0.66(3) 1 calc R U P B 2
C26B C 0.6670(10) 0.4714(10) 0.5581(9) 0.0548(18) Uani 0.66(3) 1 d D U P B 2
H26B H 0.655456 0.537010 0.508139 0.066 Uiso 0.66(3) 1 calc R U P B 2
C27 C 0.6933(3) 0.4993(3) 0.6858(3) 0.0637(8) Uani 1 1 d . . . . .
C28 C 0.6922(3) 0.4207(3) 0.7750(3) 0.0757(9) Uani 1 1 d . . . . .
H28 H 0.679087 0.336331 0.757903 0.091 Uiso 1 1 calc R U . . .
C29 C 0.7096(3) 0.4630(4) 0.8876(3) 0.0871(10) Uani 1 1 d . . . . .
H29 H 0.708293 0.407974 0.947915 0.105 Uiso 1 1 calc R U . . .
C30 C 0.7291(3) 0.5850(4) 0.9134(3) 0.0913(12) Uani 1 1 d . . . . .
H30 H 0.740281 0.614348 0.991424 0.110 Uiso 1 1 calc R U . . .
C31 C 0.7324(3) 0.6642(4) 0.8263(4) 0.0866(11) Uani 1 1 d . . . . .
H31 H 0.747523 0.748212 0.844215 0.104 Uiso 1 1 calc R U . . .
C32 C 0.7137(3) 0.6222(3) 0.7132(3) 0.0736(9) Uani 1 1 d . . . . .
H32 H 0.714816 0.677740 0.653280 0.088 Uiso 1 1 calc R U . . .


_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(3) . ?
Br2 C3 1.891(2) . ?
O1 H1 0.8400 . ?
O1 C6 1.348(3) . ?
O2 H2 0.8400 . ?
O2 C4 1.350(3) . ?
N1 C7 1.316(4) . ?
N1 C11 1.325(4) . ?
C1 C2 1.378(3) . ?
C1 C6 1.391(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(4) . ?
C3 C4 1.387(4) . ?
C4 C5 1.385(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.372(4) . ?
C9 C10 1.372(4) . ?
C9 C12A 1.425(16) . ?
C9 C12B 1.495(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(5) . ?
C11 H11 0.9500 . ?
C12A C13A 1.14(2) . ?
C13A C14A 1.377(13) . ?
C14A C19A 1.3900 . ?
C14A C15A 1.3900 . ?
C19A H19A 0.9500 . ?
C19A C18A 1.3900 . ?
C18A H18A 0.9500 . ?
C18A C17A 1.3900 . ?
C17A H17A 0.9500 . ?
C17A C16A 1.3900 . ?
C16A H16A 0.9500 . ?
C16A C15A 1.3900 . ?
C15A H15A 0.9500 . ?
C12B H12B 0.9500 . ?
C12B C13B 1.336(14) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.517(9) . ?
C14B C19B 1.3900 . ?
C14B C15B 1.3900 . ?
C19B H19B 0.9500 . ?
C19B C18B 1.3900 . ?
C18B H18B 0.9500 . ?
C18B C17B 1.3900 . ?
C17B H17B 0.9500 . ?
C17B C16B 1.3900 . ?
C16B H16B 0.9500 . ?
C16B C15B 1.3900 . ?
C15B H15B 0.9500 . ?
N2 C20 1.335(4) . ?
N2 C24 1.331(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.363(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(4) . ?
C22 C23 1.392(4) . ?
C22 C25A 1.368(18) . ?
C22 C25B 1.513(10) . ?
C23 H23 0.9500 . ?
C23 C24 1.364(4) . ?
C24 H24 0.9500 . ?
C25A C26A 1.14(3) . ?
C26A C27 1.423(17) . ?
C25B H25B 0.9500 . ?
C25B C26B 1.361(15) . ?
C26B H26B 0.9500 . ?
C26B C27 1.504(10) . ?
C27 C28 1.383(5) . ?
C27 C32 1.390(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.371(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.376(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.371(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.375(5) . ?
C32 H32 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
C6 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C11 116.2(3) . . ?
C2 C1 Br1 119.43(18) . . ?
C2 C1 C6 121.1(2) . . ?
C6 C1 Br1 119.47(19) . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 119.9(2) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 Br2 119.68(19) . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 Br2 119.9(2) . . ?
O2 C4 C3 118.7(2) . . ?
O2 C4 C5 122.7(2) . . ?
C5 C4 C3 118.6(2) . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
O1 C6 C1 118.7(2) . . ?
O1 C6 C5 123.4(2) . . ?
C5 C6 C1 117.8(2) . . ?
N1 C7 H7 118.3 . . ?
N1 C7 C8 123.3(3) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C12A 131.5(7) . . ?
C8 C9 C12B 114.0(4) . . ?
C10 C9 C8 116.6(3) . . ?
C10 C9 C12A 111.9(7) . . ?
C10 C9 C12B 129.3(4) . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
N1 C11 C10 124.3(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C13A C12A C9 172(2) . . ?
C12A C13A C14A 175(2) . . ?
C13A C14A C19A 118.7(8) . . ?
C13A C14A C15A 121.3(8) . . ?
C19A C14A C15A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C14A C19A C18A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C17A C18A C19A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C9 C12B H12B 118.5 . . ?
C13B C12B C9 123.0(9) . . ?
C13B C12B H12B 118.5 . . ?
C12B C13B H13B 117.7 . . ?
C12B C13B C14B 124.7(9) . . ?
C14B C13B H13B 117.7 . . ?
C19B C14B C13B 119.5(5) . . ?
C19B C14B C15B 120.0 . . ?
C15B C14B C13B 120.5(5) . . ?
C14B C19B H19B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C24 N2 C20 115.9(3) . . ?
N2 C20 H20 118.1 . . ?
N2 C20 C21 123.8(3) . . ?
C21 C20 H20 118.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 115.8(3) . . ?
C21 C22 C25B 116.2(5) . . ?
C23 C22 C25B 128.0(5) . . ?
C25A C22 C21 134.2(11) . . ?
C25A C22 C23 110.0(11) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
N2 C24 C23 124.1(3) . . ?
N2 C24 H24 118.0 . . ?
C23 C24 H24 118.0 . . ?
C26A C25A C22 174(3) . . ?
C25A C26A C27 169(3) . . ?
C22 C25B H25B 119.2 . . ?
C26B C25B C22 121.5(13) . . ?
C26B C25B H25B 119.2 . . ?
C25B C26B H26B 118.4 . . ?
C25B C26B C27 123.2(14) . . ?
C27 C26B H26B 118.4 . . ?
C28 C27 C26A 108.7(11) . . ?
C28 C27 C26B 128.6(5) . . ?
C28 C27 C32 118.4(3) . . ?
C32 C27 C26A 132.9(11) . . ?
C32 C27 C26B 113.0(5) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.0(4) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 H32 119.7 . . ?
C31 C32 C27 120.5(4) . . ?
C31 C32 H32 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.86 2.693(3) 173.7 . yes
O2 H2 N2 0.84 1.86 2.697(3) 172.9 . yes

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
Br1 C1 C2 C3 178.29(19) . . . . ?
Br1 C1 C6 O1 2.3(3) . . . . ?
Br1 C1 C6 C5 -177.1(2) . . . . ?
Br2 C3 C4 O2 2.4(3) . . . . ?
Br2 C3 C4 C5 -177.5(2) . . . . ?
O2 C4 C5 C6 -179.4(3) . . . . ?
N1 C7 C8 C9 1.0(6) . . . . ?
C1 C2 C3 Br2 177.52(19) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C1 C6 O1 -179.0(2) . . . . ?
C2 C1 C6 C5 1.6(4) . . . . ?
C2 C3 C4 O2 -179.3(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 O1 179.0(3) . . . . ?
C4 C5 C6 C1 -1.6(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 N1 C11 C10 -2.1(5) . . . . ?
C7 C8 C9 C10 -2.3(5) . . . . ?
C7 C8 C9 C12A 176.8(10) . . . . ?
C7 C8 C9 C12B 175.8(6) . . . . ?
C8 C9 C10 C11 1.6(5) . . . . ?
C8 C9 C12B C13B -177.9(10) . . . . ?
C9 C10 C11 N1 0.6(5) . . . . ?
C9 C12B C13B C14B 175.5(8) . . . . ?
C10 C9 C12B C13B -0.1(15) . . . . ?
C11 N1 C7 C8 1.2(5) . . . . ?
C12A C9 C10 C11 -177.7(9) . . . . ?
C13A C14A C19A C18A 177.3(14) . . . . ?
C13A C14A C15A C16A -177.2(15) . . . . ?
C14A C19A C18A C17A 0.0 . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?
C19A C18A C17A C16A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C17A C16A C15A C14A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C12B C9 C10 C11 -176.2(6) . . . . ?
C12B C13B C14B C19B 179.8(10) . . . . ?
C12B C13B C14B C15B -0.8(14) . . . . ?
C13B C14B C19B C18B 179.4(9) . . . . ?
C13B C14B C15B C16B -179.4(9) . . . . ?
C14B C19B C18B C17B 0.0 . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C19B C18B C17B C16B 0.0 . . . . ?
C18B C17B C16B C15B 0.0 . . . . ?
C17B C16B C15B C14B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
N2 C20 C21 C22 0.9(5) . . . . ?
C20 N2 C24 C23 0.1(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C20 C21 C22 C25A 177.0(15) . . . . ?
C20 C21 C22 C25B 178.1(6) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C21 C22 C25B C26B -175.6(10) . . . . ?
C22 C23 C24 N2 0.2(5) . . . . ?
C22 C25B C26B C27 178.1(6) . . . . ?
C23 C22 C25B C26B 2.8(16) . . . . ?
C24 N2 C20 C21 -0.6(5) . . . . ?
C25A C22 C23 C24 -178.0(12) . . . . ?
C25A C26A C27 C28 145(15) . . . . ?
C25A C26A C27 C32 -38(16) . . . . ?
C26A C27 C28 C29 178.1(10) . . . . ?
C26A C27 C32 C31 -176.7(12) . . . . ?
C25B C22 C23 C24 -178.4(7) . . . . ?
C25B C26B C27 C28 -12.3(15) . . . . ?
C25B C26B C27 C32 171.9(11) . . . . ?
C26B C27 C28 C29 -175.1(6) . . . . ?
C26B C27 C32 C31 176.4(5) . . . . ?
C27 C28 C29 C30 -0.2(5) . . . . ?
C28 C27 C32 C31 0.1(5) . . . . ?
C28 C29 C30 C31 -0.7(6) . . . . ?
C29 C30 C31 C32 1.3(6) . . . . ?
C30 C31 C32 C27 -1.0(5) . . . . ?
C32 C27 C28 C29 0.6(5) . . . . ?

