# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_20230721-
_database_code_depnum_ccdc_archive 'CCDC 2325969'
loop_
_audit_author_name
_audit_author_address
'Kazuaki Ishihara'
;Nagoya University
Japan
;
_audit_update_record             
;
2024-01-17 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_audit_creation_date             2023-07-21
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 Br N6 O'
_chemical_formula_sum            'C25 H19 Br N6 O'
_chemical_formula_weight         499.37
_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
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.2893(3)
_cell_length_b                   14.1630(4)
_cell_length_c                   10.0325(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.686(3)
_cell_angle_gamma                90
_cell_volume                     1144.39(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7952
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      30.7380
_cell_measurement_theta_min      2.1200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9917
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.815
_diffrn_reflns_theta_min         2.089
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  75.00   0.50    5.00    --  -15.00  45.00   0.00  360
  2  ω   -105.00  75.00   0.50    5.00    --  -15.00  45.00  90.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0488917000
_diffrn_orient_matrix_UB_12      0.0068484000
_diffrn_orient_matrix_UB_13      0.0675495000
_diffrn_orient_matrix_UB_21      -0.0694509000
_diffrn_orient_matrix_UB_22      0.0201735000
_diffrn_orient_matrix_UB_23      0.0192957000
_diffrn_orient_matrix_UB_31      -0.0235822000
_diffrn_orient_matrix_UB_32      -0.0453214000
_diffrn_orient_matrix_UB_33      0.0187664000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_full    0.852
_reflns_Friedel_fraction_max     0.641
_reflns_number_gt                5185
_reflns_number_total             5540
_reflns_odcompleteness_completeness 89.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.75
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 2000 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5540
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.075
_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)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0655
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00O(H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00D(H00D), C00H(H00H), C00I(H00I), C00Q(H00Q),
 C00R(H00R), C00T(H00T), C00V(H00V), C00X(H00X)
2.c Idealised Me refined as rotating group:
 C00U(H00A,H00C,H00F), C00W(H00J,H00K,H00L)
;
_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
Br01 Br 0.45970(3) 0.71443(2) 0.64231(2) 0.03805(8) Uani 1 1 d . . . . .
N002 N 0.4565(2) 0.40079(14) 0.13487(15) 0.0183(3) Uani 1 1 d . . . . .
N003 N 0.1009(2) 0.53542(13) 0.58925(17) 0.0201(3) Uani 1 1 d . . . . .
N004 N 0.40059(19) 0.43387(11) 0.24705(16) 0.0149(3) Uani 1 1 d . . . . .
N005 N 0.0504(2) 0.59880(12) 0.48228(16) 0.0177(3) Uani 1 1 d . . . . .
O006 O 0.0429(3) 0.63061(14) 0.25985(17) 0.0416(5) Uani 1 1 d . . . . .
C007 C 0.1788(2) 0.33378(15) 0.06549(18) 0.0176(4) Uani 1 1 d . . . . .
C008 C 0.3472(2) 0.35132(15) 0.05044(19) 0.0193(4) Uani 1 1 d . . . . .
H008 H 0.377686 0.325106 -0.024991 0.023 Uiso 1 1 calc R . . . .
N009 N 0.5431(3) 0.64697(17) 0.1597(2) 0.0398(5) Uani 1 1 d . . . . .
C00A C 0.1162(2) 0.39160(14) 0.15573(18) 0.0174(4) Uani 1 1 d . . . . .
C00B C 0.0794(3) 0.26351(16) -0.0092(2) 0.0235(4) Uani 1 1 d . . . . .
H00B H 0.119971 0.225733 -0.069767 0.028 Uiso 1 1 calc R . . . .
N00C N 0.7917(2) 0.42819(16) 0.4379(2) 0.0324(5) Uani 1 1 d . . . . .
C00D C -0.0424(2) 0.37725(18) 0.1724(2) 0.0243(4) Uani 1 1 d . . . . .
H00D H -0.083488 0.415050 0.232572 0.029 Uiso 1 1 calc R . . . .
C00E C 0.2293(2) 0.47030(14) 0.22110(18) 0.0158(3) Uani 1 1 d . . . . .
H00E H 0.216828 0.524165 0.158162 0.019 Uiso 1 1 calc R . . . .
C00F C 0.5061(2) 0.50742(15) 0.3242(2) 0.0173(4) Uani 1 1 d . . . . .
C00G C 0.2230(2) 0.50452(13) 0.36399(18) 0.0156(3) Uani 1 1 d . . . . .
H00G H 0.199520 0.451539 0.419346 0.019 Uiso 1 1 calc R . . . .
C00H C -0.0667(3) 0.64822(19) 0.6432(2) 0.0281(5) Uani 1 1 d . . . . .
H00H H -0.127683 0.681693 0.694237 0.034 Uiso 1 1 calc R . . . .
C00I C 0.5666(3) 0.5591(2) 0.8158(2) 0.0310(5) Uani 1 1 d . . . . .
H00I H 0.588189 0.605162 0.883726 0.037 Uiso 1 1 calc R . . . .
C00J C 0.0962(3) 0.58275(16) 0.35987(19) 0.0212(4) Uani 1 1 d . . . . .
C00K C 0.5044(3) 0.58430(16) 0.6798(2) 0.0209(4) Uani 1 1 d . . . . .
C00L C -0.0518(2) 0.66921(16) 0.5141(2) 0.0217(4) Uani 1 1 d . . . . .
C00M C 0.5331(3) 0.58624(16) 0.2333(2) 0.0251(4) Uani 1 1 d . . . . .
C00N C 0.6695(2) 0.46518(16) 0.3903(2) 0.0216(4) Uani 1 1 d . . . . .
C00O C 0.4021(2) 0.54464(13) 0.42667(18) 0.0154(3) Uani 1 1 d . . . . .
H00O H 0.397311 0.613693 0.420764 0.018 Uiso 1 1 calc R . . . .
C00P C 0.4707(2) 0.51737(14) 0.57516(18) 0.0156(3) Uani 1 1 d . . . . .
C00Q C 0.5964(3) 0.4655(2) 0.8499(2) 0.0335(5) Uani 1 1 d . . . . .
H00Q H 0.639491 0.448339 0.940779 0.040 Uiso 1 1 calc R . . . .
C00R C -0.0813(3) 0.25020(18) 0.0074(2) 0.0286(5) Uani 1 1 d . . . . .
H00R H -0.148711 0.203801 -0.042840 0.034 Uiso 1 1 calc R . . . .
C00S C 0.0288(3) 0.56545(17) 0.6850(2) 0.0259(5) Uani 1 1 d . . . . .
C00T C -0.1410(3) 0.30610(18) 0.0990(2) 0.0278(5) Uani 1 1 d . . . . .
H00T H -0.247396 0.295978 0.111306 0.033 Uiso 1 1 calc R . . . .
C00U C 0.0532(4) 0.5134(3) 0.8169(3) 0.0450(7) Uani 1 1 d . . . . .
H00A H -0.051304 0.488453 0.826285 0.068 Uiso 1 1 calc GR . . . .
H00C H 0.096650 0.555574 0.891690 0.068 Uiso 1 1 calc GR . . . .
H00F H 0.129914 0.462449 0.818064 0.068 Uiso 1 1 calc GR . . . .
C00V C 0.5621(3) 0.39696(18) 0.7485(2) 0.0290(5) Uani 1 1 d . . . . .
H00V H 0.581191 0.333654 0.771551 0.035 Uiso 1 1 calc R . . . .
C00W C -0.1160(3) 0.75085(17) 0.4237(2) 0.0297(5) Uani 1 1 d . . . . .
H00J H -0.024766 0.789520 0.413018 0.045 Uiso 1 1 calc GR . . . .
H00K H -0.189403 0.787503 0.464142 0.045 Uiso 1 1 calc GR . . . .
H00L H -0.175291 0.728179 0.335468 0.045 Uiso 1 1 calc GR . . . .
C00X C 0.4995(3) 0.42267(15) 0.6133(2) 0.0209(4) Uani 1 1 d . . . . .
H00X H 0.476070 0.376068 0.546159 0.025 Uiso 1 1 calc R . . . .


_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
Br01 C00K 1.900(2) . ?
N002 N004 1.396(2) . ?
N002 C008 1.291(3) . ?
N003 N005 1.386(2) . ?
N003 C00S 1.317(3) . ?
N004 C00E 1.475(2) . ?
N004 C00F 1.459(3) . ?
N005 C00J 1.387(2) . ?
N005 C00L 1.393(3) . ?
O006 C00J 1.205(3) . ?
C007 C008 1.460(3) . ?
C007 C00A 1.408(3) . ?
C007 C00B 1.392(3) . ?
N009 C00M 1.149(3) . ?
C00A C00D 1.378(3) . ?
C00A C00E 1.504(3) . ?
C00B C00R 1.394(3) . ?
N00C C00N 1.140(3) . ?
C00D C00T 1.393(3) . ?
C00E C00G 1.526(2) . ?
C00F C00M 1.492(3) . ?
C00F C00N 1.486(3) . ?
C00F C00O 1.580(3) . ?
C00G C00J 1.521(3) . ?
C00G C00O 1.575(3) . ?
C00H C00L 1.363(3) . ?
C00H C00S 1.421(3) . ?
C00I C00K 1.387(3) . ?
C00I C00Q 1.375(4) . ?
C00K C00P 1.392(3) . ?
C00L C00W 1.488(3) . ?
C00O C00P 1.514(2) . ?
C00P C00X 1.400(3) . ?
C00Q C00V 1.386(4) . ?
C00R C00T 1.389(3) . ?
C00S C00U 1.487(3) . ?
C00V C00X 1.382(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 N002 N004 113.30(15) . . ?
C00S N003 N005 104.45(17) . . ?
N002 N004 C00E 117.70(14) . . ?
N002 N004 C00F 113.32(15) . . ?
C00F N004 C00E 105.96(15) . . ?
N003 N005 C00J 118.91(16) . . ?
N003 N005 C00L 112.02(16) . . ?
C00J N005 C00L 128.94(17) . . ?
C00A C007 C008 118.33(18) . . ?
C00B C007 C008 121.61(18) . . ?
C00B C007 C00A 120.05(18) . . ?
N002 C008 C007 124.36(17) . . ?
C007 C00A C00E 115.14(17) . . ?
C00D C00A C007 119.96(19) . . ?
C00D C00A C00E 124.79(18) . . ?
C007 C00B C00R 119.51(19) . . ?
C00A C00D C00T 120.0(2) . . ?
N004 C00E C00A 107.02(15) . . ?
N004 C00E C00G 101.00(13) . . ?
C00A C00E C00G 119.26(16) . . ?
N004 C00F C00M 111.55(16) . . ?
N004 C00F C00N 108.55(17) . . ?
N004 C00F C00O 103.47(14) . . ?
C00M C00F C00O 109.40(17) . . ?
C00N C00F C00M 108.73(17) . . ?
C00N C00F C00O 115.10(16) . . ?
C00E C00G C00O 104.54(14) . . ?
C00J C00G C00E 112.51(14) . . ?
C00J C00G C00O 109.15(16) . . ?
C00L C00H C00S 106.92(18) . . ?
C00Q C00I C00K 119.7(2) . . ?
N005 C00J C00G 115.31(16) . . ?
O006 C00J N005 121.46(19) . . ?
O006 C00J C00G 123.18(18) . . ?
C00I C00K Br01 117.03(17) . . ?
C00I C00K C00P 121.8(2) . . ?
C00P C00K Br01 121.10(15) . . ?
N005 C00L C00W 124.45(19) . . ?
C00H C00L N005 104.97(19) . . ?
C00H C00L C00W 130.5(2) . . ?
N009 C00M C00F 175.6(3) . . ?
N00C C00N C00F 176.3(2) . . ?
C00G C00O C00F 103.17(14) . . ?
C00P C00O C00F 114.79(16) . . ?
C00P C00O C00G 113.57(15) . . ?
C00K C00P C00O 121.98(18) . . ?
C00K C00P C00X 117.11(18) . . ?
C00X C00P C00O 120.90(17) . . ?
C00I C00Q C00V 119.9(2) . . ?
C00T C00R C00B 120.1(2) . . ?
N003 C00S C00H 111.62(19) . . ?
N003 C00S C00U 120.0(2) . . ?
C00H C00S C00U 128.4(2) . . ?
C00R C00T C00D 120.3(2) . . ?
C00X C00V C00Q 120.0(2) . . ?
C00V C00X C00P 121.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.784
