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

data_cxy0664_0m
_audit_creation_date               2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C25 H25 Br N4 O3'
_chemical_formula_sum              'C25 H25 Br N4 O3'
_chemical_formula_weight           509.40
_chemical_absolute_configuration   ad
_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        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'

_cell_length_a                     10.9181(4)
_cell_length_b                     12.5117(5)
_cell_length_c                     17.7197(7)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2420.58(16)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9982
_cell_measurement_temperature      173
_cell_measurement_theta_max        26.31
_cell_measurement_theta_min        2.30
_shelx_estimated_absorpt_T_max     0.559
_shelx_estimated_absorpt_T_min     0.510
_exptl_absorpt_coefficient_mu      1.732
_exptl_absorpt_correction_T_max    0.7454
_exptl_absorpt_correction_T_min    0.5927
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1027 before and 0.0520 after correction. The Ratio of minimum to maximum transmission is 0.7951. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.398
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1048
_exptl_crystal_size_max            0.45
_exptl_crystal_size_mid            0.39
_exptl_crystal_size_min            0.38
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0365
_diffrn_reflns_av_unetI/netI       0.0323
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         13
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         15
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         22
_diffrn_reflns_limit_l_min         -21
_diffrn_reflns_number              21960
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           26.490
_diffrn_reflns_theta_min           2.191
_diffrn_ambient_temperature        173
_diffrn_detector                   'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CMOS area detector'
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device         'three-circle diffractometer'
_diffrn_measurement_device_type    'Bruker CMOS area detector'
_diffrn_measurement_method         'ω and φ scans'
_diffrn_radiation_monochromator    'mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_type                'Incoatec I\ms'
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.767
_reflns_Friedel_fraction_full      0.998
_reflns_Friedel_fraction_max       0.996
_reflns_number_gt                  4293
_reflns_number_total               5001
_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 V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL (Sheldrick, 2008)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.879
_refine_diff_density_min           -0.704
_refine_diff_density_rms           0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.010(3)
_refine_ls_extinction_coef         0.0057(8)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref     1.023
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       303
_refine_ls_number_reflns           5001
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0501
_refine_ls_R_factor_gt             0.0379
_refine_ls_restrained_S_all        1.023
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0347P)²+1.8811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0855
_refine_ls_wR_factor_ref           0.0915
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1), N3(H3), N4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C13(H13), C24(H24), C2(H2), C12(H12), C25(H25), C17(H17), C16(H16),
 C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C11(H11A,H11B,H11C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens     mixed
_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 0.57990(4) 0.49930(5) 0.38133(3) 0.0654(2) Uani 1 1 d . . . . .
 O1 O -0.1026(2) 0.3962(2) 0.05445(14) 0.0315(6) Uani 1 1 d . . . . .
 H1 H -0.142263 0.444944 0.076064 0.047 Uiso 1 1 d R . . . .
 O2 O -0.3917(3) 0.6280(2) 0.19220(16) 0.0395(7) Uani 1 1 d . . . . .
 O3 O -0.2601(2) 0.5297(2) 0.12241(16) 0.0365(7) Uani 1 1 d . . . . .
 N2 N 0.0541(3) 0.2810(2) 0.09255(16) 0.0234(6) Uani 1 1 d . . . . .
 N1 N 0.1587(3) 0.2806(2) 0.13453(16) 0.0232(6) Uani 1 1 d . . . . .
 N3 N -0.0854(3) 0.5620(3) 0.23295(17) 0.0312(7) Uani 1 1 d . . . . .
 H3 H -0.091428 0.498826 0.219238 0.037 Uiso 1 1 d R . . . .
 N4 N -0.2070(3) 0.5974(3) 0.23699(18) 0.0365(8) Uani 1 1 d . . . . .
 H4 H -0.233759 0.629130 0.278121 0.044 Uiso 1 1 d R . . . .
 C6 C 0.0021(3) 0.3794(3) 0.09181(19) 0.0240(7) Uani 1 1 d . . . . .
 C8 C 0.0681(3) 0.5655(3) 0.1339(2) 0.0224(7) Uani 1 1 d . . . . .
 C9 C -0.0116(3) 0.6190(3) 0.1814(2) 0.0255(8) Uani 1 1 d . . . . .
 C7 C 0.0756(3) 0.4477(3) 0.1329(2) 0.0235(8) Uani 1 1 d . . . . .
 C4 C 0.2724(3) 0.4094(3) 0.2102(2) 0.0257(8) Uani 1 1 d . . . . .
 C5 C 0.1709(3) 0.3806(3) 0.15897(18) 0.0215(7) Uani 1 1 d . . . . .
 C15 C 0.1452(3) 0.6267(3) 0.0846(2) 0.0248(7) Uani 1 1 d . . . . .
 C3 C 0.3789(3) 0.3497(3) 0.2136(2) 0.0308(9) Uani 1 1 d . . . . .
 H3A H 0.388393 0.289681 0.181245 0.037 Uiso 1 1 calc R . . . .
 C13 C 0.0616(4) 0.7904(3) 0.1389(2) 0.0323(9) Uani 1 1 d . . . . .
 H13 H 0.060554 0.866148 0.142068 0.039 Uiso 1 1 calc R . . . .
 C14 C 0.1419(4) 0.7400(3) 0.0873(2) 0.0284(8) Uani 1 1 d . . . . .
 C1 C 0.4574(4) 0.4627(3) 0.3107(2) 0.0395(10) Uani 1 1 d . . . . .
 C24 C 0.2607(3) 0.4963(4) 0.2588(2) 0.0389(9) Uani 1 1 d . . . . .
 H24 H 0.188300 0.538345 0.257477 0.047 Uiso 1 1 calc R . . . .
 C2 C 0.4716(4) 0.3761(4) 0.2634(2) 0.0398(10) Uani 1 1 d . . . . .
 H2 H 0.544593 0.334802 0.264979 0.048 Uiso 1 1 calc R . . . .
 C12 C -0.0137(4) 0.7326(3) 0.1840(2) 0.0328(9) Uani 1 1 d . . . . .
 H12 H -0.068172 0.768147 0.217499 0.039 Uiso 1 1 calc R . . . .
 C10 C -0.2843(4) 0.5810(3) 0.1787(2) 0.0330(9) Uani 1 1 d . . . . .
 C25 C 0.3531(4) 0.5223(4) 0.3089(3) 0.0472(12) Uani 1 1 d . . . . .
 H25 H 0.343801 0.581463 0.342059 0.057 Uiso 1 1 calc R . . . .
 C17 C 0.2958(4) 0.6374(3) -0.0149(3) 0.0417(11) Uani 1 1 d . . . . .
 H17 H 0.348157 0.602647 -0.049943 0.050 Uiso 1 1 calc R . . . .
 C21 C 0.1033(4) 0.0949(3) 0.0631(2) 0.0399(10) Uani 1 1 d . . . . .
 H21A H 0.183714 0.118254 0.044812 0.060 Uiso 1 1 calc GR . . . .
 H21B H 0.077023 0.031728 0.034690 0.060 Uiso 1 1 calc GR . . . .
 H21C H 0.108779 0.077181 0.116810 0.060 Uiso 1 1 calc GR . . . .
 C16 C 0.2238(4) 0.5779(3) 0.0321(2) 0.0331(9) Uani 1 1 d . . . . .
 H16 H 0.226804 0.502094 0.029130 0.040 Uiso 1 1 calc R . . . .
 C19 C 0.2177(4) 0.7993(3) 0.0380(3) 0.0379(10) Uani 1 1 d . . . . .
 H19 H 0.215663 0.875198 0.039723 0.045 Uiso 1 1 calc R . . . .
 C20 C 0.0119(4) 0.1834(3) 0.0521(2) 0.0337(9) Uani 1 1 d . . . . .
 C18 C 0.2931(4) 0.7499(3) -0.0119(3) 0.0437(11) Uani 1 1 d . . . . .
 H18 H 0.343824 0.790861 -0.044458 0.052 Uiso 1 1 calc R . . . .
 C11 C -0.4822(4) 0.6176(4) 0.1333(3) 0.0465(11) Uani 1 1 d . . . . .
 H11A H -0.451121 0.650277 0.086845 0.070 Uiso 1 1 calc GR . . . .
 H11B H -0.557731 0.653818 0.148776 0.070 Uiso 1 1 calc GR . . . .
 H11C H -0.499154 0.541767 0.124400 0.070 Uiso 1 1 calc GR . . . .
 C22 C -0.1105(5) 0.1521(4) 0.0879(4) 0.0720(18) Uani 1 1 d . . . . .
 H22A H -0.098525 0.138327 0.141836 0.108 Uiso 1 1 calc GR . . . .
 H22B H -0.141957 0.087483 0.063404 0.108 Uiso 1 1 calc GR . . . .
 H22C H -0.169345 0.210528 0.081391 0.108 Uiso 1 1 calc GR . . . .
 C23 C -0.0021(7) 0.2081(4) -0.0308(3) 0.081(2) Uani 1 1 d . . . . .
 H23A H -0.064743 0.263372 -0.037527 0.122 Uiso 1 1 calc GR . . . .
 H23B H -0.026731 0.143237 -0.057836 0.122 Uiso 1 1 calc GR . . . .
 H23C H 0.076187 0.233784 -0.050934 0.122 Uiso 1 1 calc GR . . . .


_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 1.889(4) . ?
 O1 H1 0.8400 . ?
 O1 C6 1.338(4) . ?
 O2 C10 1.333(5) . ?
 O2 C11 1.443(5) . ?
 O3 C10 1.214(5) . ?
 N2 N1 1.364(4) . ?
 N2 C6 1.356(4) . ?
 N2 C20 1.490(5) . ?
 N1 C5 1.331(5) . ?
 N3 H3 0.8290 . ?
 N3 N4 1.402(5) . ?
 N3 C9 1.412(5) . ?
 N4 H4 0.8800 . ?
 N4 C10 1.350(5) . ?
 C6 C7 1.379(5) . ?
 C8 C9 1.383(5) . ?
 C8 C7 1.476(4) . ?
 C8 C15 1.434(5) . ?
 C9 C12 1.423(5) . ?
 C7 C5 1.414(5) . ?
 C4 C5 1.477(5) . ?
 C4 C3 1.384(5) . ?
 C4 C24 1.392(6) . ?
 C15 C14 1.419(5) . ?
 C15 C16 1.406(5) . ?
 C3 H3A 0.9500 . ?
 C3 C2 1.383(6) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.415(6) . ?
 C13 C12 1.355(6) . ?
 C14 C19 1.415(6) . ?
 C1 C2 1.379(6) . ?
 C1 C25 1.361(6) . ?
 C24 H24 0.9500 . ?
 C24 C25 1.383(5) . ?
 C2 H2 0.9500 . ?
 C12 H12 0.9500 . ?
 C25 H25 0.9500 . ?
 C17 H17 0.9500 . ?
 C17 C16 1.366(6) . ?
 C17 C18 1.409(6) . ?
 C21 H21A 0.9800 . ?
 C21 H21B 0.9800 . ?
 C21 H21C 0.9800 . ?
 C21 C20 1.503(5) . ?
 C16 H16 0.9500 . ?
 C19 H19 0.9500 . ?
 C19 C18 1.357(6) . ?
 C20 C22 1.530(7) . ?
 C20 C23 1.509(6) . ?
 C18 H18 0.9500 . ?
 C11 H11A 0.9800 . ?
 C11 H11B 0.9800 . ?
 C11 H11C 0.9800 . ?
 C22 H22A 0.9800 . ?
 C22 H22B 0.9800 . ?
 C22 H22C 0.9800 . ?
 C23 H23A 0.9800 . ?
 C23 H23B 0.9800 . ?
 C23 H23C 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C6 O1 H1 109.2 . . ?
 C10 O2 C11 115.6(3) . . ?
 N1 N2 C20 121.3(3) . . ?
 C6 N2 N1 111.0(3) . . ?
 C6 N2 C20 127.7(3) . . ?
 C5 N1 N2 104.9(3) . . ?
 N4 N3 H3 103.9 . . ?
 N4 N3 C9 114.5(3) . . ?
 C9 N3 H3 109.7 . . ?
 N3 N4 H4 119.9 . . ?
 C10 N4 N3 120.3(3) . . ?
 C10 N4 H4 119.7 . . ?
 O1 C6 N2 120.4(3) . . ?
 O1 C6 C7 131.3(3) . . ?
 N2 C6 C7 108.3(3) . . ?
 C9 C8 C7 121.8(4) . . ?
 C9 C8 C15 118.7(3) . . ?
 C15 C8 C7 119.5(4) . . ?
 N3 C9 C12 118.3(3) . . ?
 C8 C9 N3 120.5(3) . . ?
 C8 C9 C12 121.0(3) . . ?
 C6 C7 C8 126.3(4) . . ?
 C6 C7 C5 103.5(3) . . ?
 C5 C7 C8 129.0(4) . . ?
 C3 C4 C5 121.7(3) . . ?
 C3 C4 C24 118.2(3) . . ?
 C24 C4 C5 120.1(3) . . ?
 N1 C5 C7 112.2(3) . . ?
 N1 C5 C4 120.3(3) . . ?
 C7 C5 C4 127.5(3) . . ?
 C14 C15 C8 119.9(3) . . ?
 C16 C15 C8 122.0(3) . . ?
 C16 C15 C14 118.1(3) . . ?
 C4 C3 H3A 119.5 . . ?
 C2 C3 C4 120.9(4) . . ?
 C2 C3 H3A 119.5 . . ?
 C14 C13 H13 119.3 . . ?
 C12 C13 H13 119.3 . . ?
 C12 C13 C14 121.3(3) . . ?
 C13 C14 C15 118.9(4) . . ?
 C13 C14 C19 121.9(3) . . ?
 C19 C14 C15 119.3(4) . . ?
 C2 C1 Br1 120.9(3) . . ?
 C25 C1 Br1 118.3(3) . . ?
 C25 C1 C2 120.7(4) . . ?
 C4 C24 H24 119.5 . . ?
 C25 C24 C4 121.0(4) . . ?
 C25 C24 H24 119.5 . . ?
 C3 C2 H2 120.2 . . ?
 C1 C2 C3 119.5(4) . . ?
 C1 C2 H2 120.2 . . ?
 C9 C12 H12 119.9 . . ?
 C13 C12 C9 120.2(4) . . ?
 C13 C12 H12 119.9 . . ?
 O2 C10 N4 110.2(3) . . ?
 O3 C10 O2 124.9(4) . . ?
 O3 C10 N4 125.0(4) . . ?
 C1 C25 C24 119.7(4) . . ?
 C1 C25 H25 120.1 . . ?
 C24 C25 H25 120.1 . . ?
 C16 C17 H17 119.7 . . ?
 C16 C17 C18 120.7(4) . . ?
 C18 C17 H17 119.7 . . ?
 H21A C21 H21B 109.5 . . ?
 H21A C21 H21C 109.5 . . ?
 H21B C21 H21C 109.5 . . ?
 C20 C21 H21A 109.5 . . ?
 C20 C21 H21B 109.5 . . ?
 C20 C21 H21C 109.5 . . ?
 C15 C16 H16 119.4 . . ?
 C17 C16 C15 121.2(4) . . ?
 C17 C16 H16 119.4 . . ?
 C14 C19 H19 119.4 . . ?
 C18 C19 C14 121.2(4) . . ?
 C18 C19 H19 119.4 . . ?
 N2 C20 C21 109.6(3) . . ?
 N2 C20 C22 106.2(4) . . ?
 N2 C20 C23 109.4(4) . . ?
 C21 C20 C22 109.8(4) . . ?
 C21 C20 C23 110.1(4) . . ?
 C23 C20 C22 111.6(5) . . ?
 C17 C18 H18 120.2 . . ?
 C19 C18 C17 119.5(4) . . ?
 C19 C18 H18 120.2 . . ?
 O2 C11 H11A 109.5 . . ?
 O2 C11 H11B 109.5 . . ?
 O2 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?
 C20 C22 H22A 109.5 . . ?
 C20 C22 H22B 109.5 . . ?
 C20 C22 H22C 109.5 . . ?
 H22A C22 H22B 109.5 . . ?
 H22A C22 H22C 109.5 . . ?
 H22B C22 H22C 109.5 . . ?
 C20 C23 H23A 109.5 . . ?
 C20 C23 H23B 109.5 . . ?
 C20 C23 H23C 109.5 . . ?
 H23A C23 H23B 109.5 . . ?
 H23A C23 H23C 109.5 . . ?
 H23B C23 H23C 109.5 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Br1 C1 C2 C3 178.3(3) . . . . ?
 Br1 C1 C25 C24 -178.8(4) . . . . ?
 O1 C6 C7 C8 -12.7(7) . . . . ?
 O1 C6 C7 C5 179.0(4) . . . . ?
 N2 N1 C5 C7 -0.6(4) . . . . ?
 N2 N1 C5 C4 176.8(3) . . . . ?
 N2 C6 C7 C8 166.6(4) . . . . ?
 N2 C6 C7 C5 -1.8(4) . . . . ?
 N1 N2 C6 O1 -179.1(3) . . . . ?
 N1 N2 C6 C7 1.5(4) . . . . ?
 N1 N2 C20 C21 -2.6(5) . . . . ?
 N1 N2 C20 C22 116.0(4) . . . . ?
 N1 N2 C20 C23 -123.4(4) . . . . ?
 N3 N4 C10 O2 -175.3(3) . . . . ?
 N3 N4 C10 O3 5.6(6) . . . . ?
 N3 C9 C12 C13 175.7(4) . . . . ?
 N4 N3 C9 C8 -136.6(4) . . . . ?
 N4 N3 C9 C12 48.7(5) . . . . ?
 C6 N2 N1 C5 -0.6(4) . . . . ?
 C6 N2 C20 C21 174.7(3) . . . . ?
 C6 N2 C20 C22 -66.7(5) . . . . ?
 C6 N2 C20 C23 53.8(6) . . . . ?
 C6 C7 C5 N1 1.5(4) . . . . ?
 C6 C7 C5 C4 -175.7(3) . . . . ?
 C8 C9 C12 C13 0.9(6) . . . . ?
 C8 C7 C5 N1 -166.4(4) . . . . ?
 C8 C7 C5 C4 16.4(6) . . . . ?
 C8 C15 C14 C13 -0.2(5) . . . . ?
 C8 C15 C14 C19 -179.5(4) . . . . ?
 C8 C15 C16 C17 179.4(4) . . . . ?
 C9 N3 N4 C10 69.8(5) . . . . ?
 C9 C8 C7 C6 85.2(5) . . . . ?
 C9 C8 C7 C5 -109.4(5) . . . . ?
 C9 C8 C15 C14 2.4(5) . . . . ?
 C9 C8 C15 C16 -176.6(4) . . . . ?
 C7 C8 C9 N3 2.6(6) . . . . ?
 C7 C8 C9 C12 177.2(4) . . . . ?
 C7 C8 C15 C14 -177.6(4) . . . . ?
 C7 C8 C15 C16 3.5(6) . . . . ?
 C4 C3 C2 C1 0.4(6) . . . . ?
 C4 C24 C25 C1 0.5(7) . . . . ?
 C5 C4 C3 C2 -178.2(3) . . . . ?
 C5 C4 C24 C25 177.8(4) . . . . ?
 C15 C8 C9 N3 -177.4(3) . . . . ?
 C15 C8 C9 C12 -2.8(5) . . . . ?
 C15 C8 C7 C6 -94.8(5) . . . . ?
 C15 C8 C7 C5 70.5(6) . . . . ?
 C15 C14 C19 C18 0.1(7) . . . . ?
 C3 C4 C5 N1 23.3(5) . . . . ?
 C3 C4 C5 C7 -159.7(4) . . . . ?
 C3 C4 C24 C25 0.1(6) . . . . ?
 C13 C14 C19 C18 -179.2(4) . . . . ?
 C14 C15 C16 C17 0.5(6) . . . . ?
 C14 C13 C12 C9 1.4(6) . . . . ?
 C14 C19 C18 C17 0.4(7) . . . . ?
 C24 C4 C5 N1 -154.3(4) . . . . ?
 C24 C4 C5 C7 22.7(6) . . . . ?
 C24 C4 C3 C2 -0.5(6) . . . . ?
 C2 C1 C25 C24 -0.6(7) . . . . ?
 C12 C13 C14 C15 -1.7(6) . . . . ?
 C12 C13 C14 C19 177.6(4) . . . . ?
 C25 C1 C2 C3 0.1(7) . . . . ?
 C16 C15 C14 C13 178.8(4) . . . . ?
 C16 C15 C14 C19 -0.5(6) . . . . ?
 C16 C17 C18 C19 -0.4(8) . . . . ?
 C20 N2 N1 C5 177.1(3) . . . . ?
 C20 N2 C6 O1 3.4(5) . . . . ?
 C20 N2 C6 C7 -176.0(3) . . . . ?
 C18 C17 C16 C15 0.0(7) . . . . ?
 C11 O2 C10 O3 -1.8(6) . . . . ?
 C11 O2 C10 N4 179.2(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
