# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_mat719_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2r2srd
_database_code_depnum_ccdc_archive 'CCDC 2534924'
loop_
_audit_author_name
_audit_author_address
'Kotaro Matsumura'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2026-03-04 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-10-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            11-OH
_chemical_name_systematic        
2-Bromo-5-(4-methoxyphenyl)-6,7-dipentyl-11-hydroxydibenzopyrrolo[1,2-a][1,8]naphthyridine
_chemical_formula_moiety         'C36 H37 Br N2 O2'
_chemical_formula_sum            'C36 H37 Br N2 O2'
_chemical_formula_weight         609.58
_chemical_melting_point          496-497
_chemical_oxdiff_formula         C100H100N10O10Br
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   11.4668(3)
_cell_length_b                   12.1256(4)
_cell_length_c                   12.7155(4)
_cell_angle_alpha                108.010(3)
_cell_angle_beta                 97.864(2)
_cell_angle_gamma                98.156(2)
_cell_volume                     1633.41(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12267
_cell_measurement_temperature    90
_cell_measurement_theta_max      74.2570
_cell_measurement_theta_min      3.7280
_shelx_estimated_absorpt_T_max   0.757
_shelx_estimated_absorpt_T_min   0.441
_exptl_absorpt_coefficient_mu    1.961
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17001
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.534
_diffrn_reflns_theta_min         3.725
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  37.00   0.50    0.05    --  -42.43  19.00  30.00  132
  2  ω    -86.00 -36.00   0.50    0.06    -- -104.00  77.00  30.00  100
  3  ω      5.00  38.00   0.50    0.05    --  -42.43  19.00-150.00   66
  4  ω     15.00  84.00   0.50    0.05    --   42.43-111.00 127.00  138
  5  ω     72.00 107.00   0.50    0.06    --  106.13-111.00 127.00   70
  6  ω     33.00 105.00   0.50    0.06    --  106.13 -94.00 150.00  144
  7  ω     69.00 111.00   0.50    0.06    --  106.13-125.00   0.00   84
  8  ω     35.00 109.00   0.50    0.06    --  106.13-125.00 -30.00  148
  9  ω     60.00  86.00   0.50    0.06    --  106.13-125.00 -60.00   52
 10  ω     37.00  72.00   0.50    0.06    --  106.13 -61.00   0.00   70
 11  ω     35.00  91.00   0.50    0.06    --  106.13 -77.00 150.00  112
 12  ω     33.00  70.00   0.50    0.06    --  106.13 -61.00 -30.00   74
 13  ω     40.00  65.00   0.50    0.06    --  106.13 -61.00 -60.00   50
 14  ω     38.00  71.00   0.50    0.06    --  106.13 -61.00-180.00   66
 15  ω     85.00 177.00   0.50    0.06    --  106.13  45.00 -30.00  184
 16  ω    121.00 147.00   0.50    0.06    --  106.13  61.00 -60.00   52
 17  ω     83.00 109.00   0.50    0.06    --  106.13  61.00 -60.00   52
 18  ω     32.00 115.00   0.50    0.05    --   42.43  57.00  60.00  166
 19  ω     22.00 113.00   0.50    0.05    --   42.43  57.00 -90.00  182
 20  ω    127.00 167.00   0.50    0.06    --  106.13 111.00-138.00   80
 21  ω     89.00 124.00   0.50    0.06    --  106.13 111.00-138.00   70
 22  ω     -3.00  64.00   0.50    0.05    --   42.43 -57.00 120.00  134
 23  ω    -48.00 -22.00   0.50    0.05    --  -42.43 111.00-138.00   52
 24  ω    -78.00 -50.00   0.50    0.05    --  -42.43 111.00-138.00   56
 25  ω    -60.00 -35.00   0.50    0.06    -- -104.00 144.00-136.35   50
 26  ω    -97.00 -68.00   0.50    0.06    -- -104.00 111.00-138.00   58
 27  ω   -126.00-100.00   0.50    0.06    -- -104.00 144.00-136.35   52
 28  ω   -112.00 -34.00   0.50    0.06    -- -104.00 125.00  30.00  156
 29  ω   -110.00 -54.00   0.50    0.06    -- -104.00 -15.00  60.00  112
 30  ω   -156.00-130.00   0.50    0.06    -- -104.00 -15.00  60.00   52
 31  ω   -175.00 -92.00   0.50    0.06    -- -104.00 -30.00 150.00  166
 32  ω   -110.00 -45.00   0.50    0.05    --  -42.43 -57.00 -60.00  130
 33  ω   -162.00 -80.00   0.50    0.06    -- -104.00 -61.00-150.00  164
 34  ω   -173.00 -98.00   0.50    0.06    -- -104.00 -94.00 -90.00  150
 35  ω   -121.00 -83.00   0.50    0.06    -- -104.00-125.00 -90.00   76
 36  ω   -157.00 -90.00   0.50    0.06    -- -104.00-111.00 127.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0185445000
_diffrn_orient_matrix_UB_12      0.0702760000
_diffrn_orient_matrix_UB_13      0.1267169000
_diffrn_orient_matrix_UB_21      -0.1346549000
_diffrn_orient_matrix_UB_22      0.0043974000
_diffrn_orient_matrix_UB_23      -0.0128814000
_diffrn_orient_matrix_UB_31      -0.0254846000
_diffrn_orient_matrix_UB_32      -0.1166151000
_diffrn_orient_matrix_UB_33      0.0250630000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5444
_reflns_number_total             6434
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.958
_refine_diff_density_min         -1.432
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0774
_refine_ls_restrained_S_all      1.062
_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)+(0.1552P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2126
_refine_ls_wR_factor_ref         0.2186
_refine_special_details          'Solvent Mask'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,
 H12B), C18(H18A,H18B), C19(H19A,H19B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C5(H5), C4(H4), C34(H34), C28(H28), C25(H25), C32(H32),
 C29(H29), C24(H24), C31(H31)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.47223(4) 0.26164(3) 0.97146(3) 0.04146(19) Uani 1 1 d . . . . .
O2 O 1.00770(18) 0.84275(18) 0.6630(2) 0.0317(5) Uani 1 1 d . . . . .
O1 O 0.0906(2) -0.24942(19) 0.4648(2) 0.0348(5) Uani 1 1 d . . . . .
H1 H 0.089240 -0.215151 0.532896 0.052 Uiso 1 1 calc R U . . .
N2 N 0.3920(2) 0.0940(2) 0.5279(2) 0.0214(5) Uani 1 1 d . . . . .
N1 N 0.5391(2) 0.2596(2) 0.5614(2) 0.0197(5) Uani 1 1 d . . . . .
C36 C 0.4664(2) 0.1541(2) 0.4863(2) 0.0200(6) Uani 1 1 d . . . . .
C16 C 0.7002(3) 0.3907(3) 0.3688(3) 0.0263(6) Uani 1 1 d . . . . .
H16A H 0.741536 0.346248 0.310785 0.032 Uiso 1 1 calc R U . . .
H16B H 0.762273 0.444966 0.432840 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6240(2) 0.3051(3) 0.4087(2) 0.0235(6) Uani 1 1 d . . . . .
C8 C 0.4798(2) 0.1222(2) 0.3716(2) 0.0217(6) Uani 1 1 d . . . . .
C9 C 0.5614(2) 0.1988(3) 0.3332(2) 0.0230(6) Uani 1 1 d . . . . .
C1 C 0.3203(2) -0.0092(2) 0.4560(3) 0.0225(6) Uani 1 1 d . . . . .
C7 C 0.4073(2) 0.0159(3) 0.2995(2) 0.0236(6) Uani 1 1 d . . . . .
H7 H 0.413315 -0.011440 0.222244 0.028 Uiso 1 1 calc R U . . .
C2 C 0.2405(2) -0.0747(2) 0.4993(3) 0.0246(6) Uani 1 1 d . . . . .
H2 H 0.236259 -0.046753 0.576913 0.029 Uiso 1 1 calc R U . . .
C35 C 0.5484(2) 0.3047(2) 0.6776(2) 0.0234(6) Uani 1 1 d . . . . .
C30 C 0.6292(2) 0.4149(2) 0.7153(3) 0.0248(6) Uani 1 1 d . . . . .
C5 C 0.2482(3) -0.1593(3) 0.2695(3) 0.0281(7) Uani 1 1 d . . . . .
H5 H 0.249967 -0.187980 0.191373 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7561(3) 0.5432(3) 0.6302(3) 0.0259(6) Uani 1 1 d . . . . .
C6 C 0.3254(2) -0.0512(3) 0.3398(3) 0.0241(6) Uani 1 1 d . . . . .
C4 C 0.1723(3) -0.2217(3) 0.3130(3) 0.0300(7) Uani 1 1 d . . . . .
H4 H 0.121595 -0.293847 0.265392 0.036 Uiso 1 1 calc R U . . .
C34 C 0.4996(3) 0.2575(3) 0.7523(2) 0.0244(6) Uani 1 1 d . . . . .
H34 H 0.445878 0.183262 0.726764 0.029 Uiso 1 1 calc R U . . .
C21 C 0.6144(2) 0.3382(2) 0.5260(3) 0.0219(6) Uani 1 1 d . . . . .
C3 C 0.1684(3) -0.1796(3) 0.4291(3) 0.0279(6) Uani 1 1 d . . . . .
C17 C 0.6230(3) 0.4626(3) 0.3192(3) 0.0315(7) Uani 1 1 d . . . . .
H17A H 0.553144 0.407741 0.264314 0.038 Uiso 1 1 calc R U . . .
H17B H 0.591953 0.515712 0.380564 0.038 Uiso 1 1 calc R U . . .
C26 C 0.9200(3) 0.7476(3) 0.6544(3) 0.0280(6) Uani 1 1 d . . . . .
C28 C 0.7995(3) 0.7523(2) 0.6530(3) 0.0261(6) Uani 1 1 d . . . . .
H28 H 0.772277 0.824174 0.659594 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6692(2) 0.4354(2) 0.6203(3) 0.0241(6) Uani 1 1 d . . . . .
C10 C 0.5765(3) 0.1576(3) 0.2120(3) 0.0265(6) Uani 1 1 d . . . . .
H10A H 0.596874 0.227158 0.188157 0.032 Uiso 1 1 calc R U . . .
H10B H 0.499635 0.109204 0.163723 0.032 Uiso 1 1 calc R U . . .
C25 C 0.9589(3) 0.6416(3) 0.6447(3) 0.0357(8) Uani 1 1 d . . . . .
H25 H 1.041427 0.638778 0.645672 0.043 Uiso 1 1 calc R U . . .
C33 C 0.5332(3) 0.3242(3) 0.8662(3) 0.0291(6) Uani 1 1 d . . . . .
C32 C 0.6114(3) 0.4345(3) 0.9056(3) 0.0337(7) Uani 1 1 d . . . . .
H32 H 0.631870 0.477717 0.984085 0.040 Uiso 1 1 calc R U . . .
C29 C 0.7187(3) 0.6493(3) 0.6417(3) 0.0270(6) Uani 1 1 d . . . . .
H29 H 0.636375 0.652317 0.641926 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6752(3) 0.0843(3) 0.1951(3) 0.0281(6) Uani 1 1 d . . . . .
H11A H 0.751257 0.131727 0.245533 0.034 Uiso 1 1 calc R U . . .
H11B H 0.653279 0.013323 0.216509 0.034 Uiso 1 1 calc R U . . .
C24 C 0.8787(3) 0.5414(3) 0.6338(3) 0.0341(8) Uani 1 1 d . . . . .
H24 H 0.906509 0.470086 0.628527 0.041 Uiso 1 1 calc R U . . .
C31 C 0.6583(3) 0.4797(3) 0.8307(3) 0.0321(7) Uani 1 1 d . . . . .
H31 H 0.710484 0.554832 0.856951 0.039 Uiso 1 1 calc R U . . .
C27 C 0.9714(3) 0.9520(3) 0.6702(3) 0.0376(8) Uani 1 1 d . . . . .
H27A H 0.915418 0.942156 0.600968 0.056 Uiso 1 1 calc R U . . .
H27B H 1.042097 1.012530 0.679591 0.056 Uiso 1 1 calc R U . . .
H27C H 0.931880 0.976354 0.734902 0.056 Uiso 1 1 calc R U . . .
C12 C 0.6945(3) 0.0456(4) 0.0738(3) 0.0387(8) Uani 1 1 d . . . . .
H12A H 0.621060 -0.008910 0.024539 0.046 Uiso 1 1 calc R U . . .
H12B H 0.707176 0.115907 0.049721 0.046 Uiso 1 1 calc R U . . .
C18 C 0.6898(3) 0.5369(3) 0.2607(3) 0.0363(7) Uani 1 1 d . . . . .
H18A H 0.735170 0.487189 0.210625 0.044 Uiso 1 1 calc R U . . .
H18B H 0.630457 0.561530 0.212810 0.044 Uiso 1 1 calc R U . . .
C19 C 0.7758(4) 0.6456(4) 0.3410(4) 0.0500(10) Uani 1 1 d . . . . .
H19A H 0.839728 0.621283 0.384428 0.060 Uiso 1 1 calc R U . . .
H19B H 0.732221 0.692710 0.395070 0.060 Uiso 1 1 calc R U . . .
C13 C 0.8009(4) -0.0156(4) 0.0581(3) 0.0482(10) Uani 1 1 d . . . . .
H13A H 0.790490 -0.083473 0.085935 0.058 Uiso 1 1 calc R U . . .
H13B H 0.875127 0.040329 0.103967 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8149(5) -0.0596(6) -0.0647(4) 0.0780(18) Uani 1 1 d . . . . .
H14A H 0.744095 -0.119456 -0.109550 0.117 Uiso 1 1 calc R U . . .
H14B H 0.886760 -0.094576 -0.070018 0.117 Uiso 1 1 calc R U . . .
H14C H 0.822687 0.006794 -0.093368 0.117 Uiso 1 1 calc R U . . .
C20 C 0.8334(4) 0.7229(5) 0.2782(6) 0.0742(17) Uani 1 1 d . . . . .
H20A H 0.875296 0.676065 0.223568 0.111 Uiso 1 1 calc R U . . .
H20B H 0.890820 0.790995 0.332508 0.111 Uiso 1 1 calc R U . . .
H20C H 0.770695 0.750827 0.238567 0.111 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 C33 1.894(3) . ?
O2 C26 1.385(4) . ?
O2 C27 1.424(4) . ?
O1 H1 0.8400 . ?
O1 C3 1.362(4) . ?
N2 C36 1.313(4) . ?
N2 C1 1.369(4) . ?
N1 C36 1.402(3) . ?
N1 C35 1.391(4) . ?
N1 C21 1.413(4) . ?
C36 C8 1.424(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.513(4) . ?
C16 C17 1.533(4) . ?
C15 C9 1.371(4) . ?
C15 C21 1.444(4) . ?
C8 C9 1.462(4) . ?
C8 C7 1.396(4) . ?
C9 C10 1.509(4) . ?
C1 C2 1.405(4) . ?
C1 C6 1.419(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.406(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(4) . ?
C35 C30 1.416(4) . ?
C35 C34 1.391(4) . ?
C30 C22 1.426(5) . ?
C30 C31 1.400(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.425(4) . ?
C5 C4 1.357(5) . ?
C23 C22 1.488(4) . ?
C23 C29 1.384(4) . ?
C23 C24 1.405(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.413(5) . ?
C34 H34 0.9500 . ?
C34 C33 1.391(4) . ?
C21 C22 1.390(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.525(5) . ?
C26 C28 1.389(4) . ?
C26 C25 1.395(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.401(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.533(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.373(4) . ?
C33 C32 1.402(5) . ?
C32 H32 0.9500 . ?
C32 C31 1.370(5) . ?
C29 H29 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(4) . ?
C24 H24 0.9500 . ?
C31 H31 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.521(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.509(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.545(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.525(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C26 O2 C27 117.7(2) . . ?
C3 O1 H1 109.5 . . ?
C36 N2 C1 118.1(3) . . ?
C36 N1 C21 122.9(3) . . ?
C35 N1 C36 127.5(2) . . ?
C35 N1 C21 109.6(2) . . ?
N2 C36 N1 117.1(3) . . ?
N2 C36 C8 125.9(3) . . ?
N1 C36 C8 116.9(3) . . ?
H16A C16 H16B 108.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 C17 110.9(2) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C9 C15 C16 120.1(3) . . ?
C9 C15 C21 120.5(3) . . ?
C21 C15 C16 119.4(3) . . ?
C36 C8 C9 121.4(3) . . ?
C7 C8 C36 115.5(3) . . ?
C7 C8 C9 123.1(3) . . ?
C15 C9 C8 119.2(3) . . ?
C15 C9 C10 121.8(3) . . ?
C8 C9 C10 119.0(3) . . ?
N2 C1 C2 118.8(3) . . ?
N2 C1 C6 121.5(3) . . ?
C2 C1 C6 119.7(3) . . ?
C8 C7 H7 119.6 . . ?
C8 C7 C6 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
N1 C35 C30 106.5(3) . . ?
C34 C35 N1 131.5(3) . . ?
C34 C35 C30 121.8(3) . . ?
C35 C30 C22 108.6(3) . . ?
C31 C30 C35 119.1(3) . . ?
C31 C30 C22 132.3(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C29 C23 C22 120.6(3) . . ?
C29 C23 C24 118.4(3) . . ?
C24 C23 C22 120.9(3) . . ?
C1 C6 C5 118.7(3) . . ?
C7 C6 C1 118.2(3) . . ?
C7 C6 C5 123.1(3) . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C35 C34 H34 121.6 . . ?
C35 C34 C33 116.8(3) . . ?
C33 C34 H34 121.6 . . ?
N1 C21 C15 118.9(2) . . ?
C22 C21 N1 107.9(3) . . ?
C22 C21 C15 133.2(3) . . ?
O1 C3 C2 123.5(3) . . ?
O1 C3 C4 115.7(3) . . ?
C2 C3 C4 120.8(3) . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C16 113.9(3) . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
O2 C26 C28 124.1(3) . . ?
O2 C26 C25 115.7(3) . . ?
C28 C26 C25 120.1(3) . . ?
C26 C28 H28 120.6 . . ?
C26 C28 C29 118.9(3) . . ?
C29 C28 H28 120.6 . . ?
C30 C22 C23 122.6(3) . . ?
C21 C22 C30 107.3(3) . . ?
C21 C22 C23 130.0(3) . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 111.9(2) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C26 C25 H25 119.8 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C34 C33 Br1 118.3(2) . . ?
C34 C33 C32 122.5(3) . . ?
C32 C33 Br1 119.1(2) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 C33 119.8(3) . . ?
C31 C32 H32 120.1 . . ?
C23 C29 C28 121.5(3) . . ?
C23 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 112.5(3) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.6 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 119.9(3) . . ?
C32 C31 H31 120.0 . . ?
O2 C27 H27A 109.5 . . ?
O2 C27 H27B 109.5 . . ?
O2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 113.2(3) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.7(3) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C18 C19 C20 111.7(4) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C12 C13 C14 112.5(3) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C33 C32 C31 178.6(3) . . . . ?
O2 C26 C28 C29 178.8(3) . . . . ?
O2 C26 C25 C24 -178.9(3) . . . . ?
N2 C36 C8 C9 176.9(2) . . . . ?
N2 C36 C8 C7 -1.2(4) . . . . ?
N2 C1 C2 C3 -179.2(3) . . . . ?
N2 C1 C6 C7 0.3(4) . . . . ?
N2 C1 C6 C5 -180.0(2) . . . . ?
N1 C36 C8 C9 -2.8(4) . . . . ?
N1 C36 C8 C7 179.2(2) . . . . ?
N1 C35 C30 C22 -0.4(3) . . . . ?
N1 C35 C30 C31 -178.4(3) . . . . ?
N1 C35 C34 C33 176.2(3) . . . . ?
N1 C21 C22 C30 1.4(3) . . . . ?
N1 C21 C22 C23 -179.9(3) . . . . ?
C36 N2 C1 C2 179.8(2) . . . . ?
C36 N2 C1 C6 0.2(4) . . . . ?
C36 N1 C35 C30 -177.8(2) . . . . ?
C36 N1 C35 C34 6.0(5) . . . . ?
C36 N1 C21 C15 -4.6(4) . . . . ?
C36 N1 C21 C22 177.4(2) . . . . ?
C36 C8 C9 C15 -1.7(4) . . . . ?
C36 C8 C9 C10 176.9(2) . . . . ?
C36 C8 C7 C6 1.6(4) . . . . ?
C16 C15 C9 C8 -174.4(2) . . . . ?
C16 C15 C9 C10 7.0(4) . . . . ?
C16 C15 C21 N1 177.4(2) . . . . ?
C16 C15 C21 C22 -5.2(5) . . . . ?
C16 C17 C18 C19 -74.8(4) . . . . ?
C15 C16 C17 C18 -171.0(3) . . . . ?
C15 C9 C10 C11 90.7(3) . . . . ?
C15 C21 C22 C30 -176.2(3) . . . . ?
C15 C21 C22 C23 2.5(5) . . . . ?
C8 C9 C10 C11 -87.9(3) . . . . ?
C8 C7 C6 C1 -1.2(4) . . . . ?
C8 C7 C6 C5 179.1(3) . . . . ?
C9 C15 C21 N1 -0.2(4) . . . . ?
C9 C15 C21 C22 177.1(3) . . . . ?
C9 C8 C7 C6 -176.4(2) . . . . ?
C9 C10 C11 C12 -178.0(3) . . . . ?
C1 N2 C36 N1 180.0(2) . . . . ?
C1 N2 C36 C8 0.3(4) . . . . ?
C1 C2 C3 O1 178.6(3) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C7 C8 C9 C15 176.2(3) . . . . ?
C7 C8 C9 C10 -5.2(4) . . . . ?
C2 C1 C6 C7 -179.3(2) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C35 N1 C36 N2 5.2(4) . . . . ?
C35 N1 C36 C8 -175.1(2) . . . . ?
C35 N1 C21 C15 176.3(2) . . . . ?
C35 N1 C21 C22 -1.7(3) . . . . ?
C35 C30 C22 C23 -179.4(2) . . . . ?
C35 C30 C22 C21 -0.6(3) . . . . ?
C35 C30 C31 C32 1.9(5) . . . . ?
C35 C34 C33 Br1 -178.4(2) . . . . ?
C35 C34 C33 C32 0.6(4) . . . . ?
C30 C35 C34 C33 0.5(4) . . . . ?
C5 C4 C3 O1 -179.1(3) . . . . ?
C5 C4 C3 C2 0.5(5) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
C34 C35 C30 C22 176.3(2) . . . . ?
C34 C35 C30 C31 -1.7(4) . . . . ?
C34 C33 C32 C31 -0.4(5) . . . . ?
C21 N1 C36 N2 -173.7(2) . . . . ?
C21 N1 C36 C8 6.0(4) . . . . ?
C21 N1 C35 C30 1.2(3) . . . . ?
C21 N1 C35 C34 -175.0(3) . . . . ?
C21 C15 C9 C8 3.2(4) . . . . ?
C21 C15 C9 C10 -175.4(3) . . . . ?
C17 C16 C15 C9 81.5(3) . . . . ?
C17 C16 C15 C21 -96.1(3) . . . . ?
C17 C18 C19 C20 -175.4(3) . . . . ?
C26 C28 C29 C23 -1.0(5) . . . . ?
C26 C25 C24 C23 1.1(6) . . . . ?
C28 C26 C25 C24 0.0(6) . . . . ?
C22 C30 C31 C32 -175.6(3) . . . . ?
C22 C23 C29 C28 178.9(3) . . . . ?
C22 C23 C24 C25 -179.0(3) . . . . ?
C10 C11 C12 C13 173.7(3) . . . . ?
C25 C26 C28 C29 0.0(5) . . . . ?
C33 C32 C31 C30 -0.9(5) . . . . ?
C29 C23 C22 C30 -78.9(4) . . . . ?
C29 C23 C22 C21 102.6(4) . . . . ?
C29 C23 C24 C25 -2.1(5) . . . . ?
C11 C12 C13 C14 176.9(4) . . . . ?
C24 C23 C22 C30 97.9(4) . . . . ?
C24 C23 C22 C21 -80.6(4) . . . . ?
C24 C23 C29 C28 2.0(5) . . . . ?
C31 C30 C22 C23 -1.8(5) . . . . ?
C31 C30 C22 C21 177.0(3) . . . . ?
C27 O2 C26 C28 -0.4(5) . . . . ?
C27 O2 C26 C25 178.4(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 1.000 246.7 54.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 6.462
_oxdiff_exptl_absorpt_empirical_full_min 0.273
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_mat716_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2r2sqc
_database_code_depnum_ccdc_archive 'CCDC 2534923'
loop_
_audit_author_name
_audit_author_address
'Kotaro Matsumura'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2026-03-04 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2024-12-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            10-OH
_chemical_name_systematic        
'2- bromo-5-(4-methoxyphenyl)-6,7-dipentyl-10-hydroxydibenzopyrrolo[1,2-a][1,8]naphthyridine'
_chemical_formula_moiety         'C36 H37 Br N2 O2, C2 H3 N'
_chemical_formula_sum            'C38 H40 Br N3 O2'
_chemical_formula_weight         650.64
_chemical_melting_point          '475--476 \%C (decomp.)'
_chemical_oxdiff_formula         C100H100N10O10
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   11.50910(10)
_cell_length_b                   11.83610(10)
_cell_length_c                   12.95870(10)
_cell_angle_alpha                106.9390(10)
_cell_angle_beta                 93.3830(10)
_cell_angle_gamma                100.1250(10)
_cell_volume                     1650.96(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15763
_cell_measurement_temperature    90.00
_cell_measurement_theta_max      74.0270
_cell_measurement_theta_min      3.9690
_shelx_estimated_absorpt_T_max   0.692
_shelx_estimated_absorpt_T_min   0.337
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19358
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.637
_diffrn_reflns_theta_min         3.590
_diffrn_ambient_temperature      90.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  38.00   0.50    0.05    --  -42.30  19.00 120.00  110
  2  ω    -28.00  38.00   0.50    0.05    --  -42.30  19.00-120.00  132
  3  ω    -30.00  38.00   0.50    0.05    --  -42.30  19.00-180.00  136
  4  ω     57.00  82.00   0.50    0.05    --   42.30-169.00  -4.00   50
  5  ω     44.00  92.00   0.50    0.05    --  106.13-125.00   0.00   96
  6  ω     40.00 142.00   0.50    0.05    --  106.13-169.00  -4.00  204
  7  ω     72.00 105.00   0.50    0.05    --  106.13 -94.00   0.00   66
  8  ω     24.00  78.00   0.50    0.05    --   42.30-114.00 139.00  108
  9  ω     47.00  72.00   0.50    0.05    --  106.13-114.00 139.00   50
 10  ω     39.00  80.00   0.50    0.05    --  106.13 -94.00 150.00   82
 11  ω     65.00  99.00   0.50    0.05    --  106.13 -94.00 -30.00   68
 12  ω     71.00 100.00   0.50    0.05    --  106.13 -77.00   0.00   58
 13  ω     32.00  64.00   0.50    0.05    --  106.13 -77.00   0.00   64
 14  ω     38.00  70.00   0.50    0.05    --  106.13 -61.00  30.00   64
 15  ω     38.00  66.00   0.50    0.05    --  106.13 -61.00   0.00   56
 16  ω    -32.00  24.00   0.50    0.05    --   42.30 -19.00 -30.00  112
 17  ω     54.00 110.00   0.50    0.05    --   42.30  77.00  30.00  112
 18  ω     77.00 102.00   0.50    0.05    --  106.13 169.00  12.00   50
 19  ω     63.00 112.00   0.50    0.05    --   42.30 169.00  12.00   98
 20  ω    133.00 177.00   0.50    0.05    --  106.13 114.00-130.00   88
 21  ω     92.00 168.00   0.50    0.05    --  106.13  45.00 -30.00  152
 22  ω     87.00 178.00   0.50    0.05    --  106.13  30.00  30.00  182
 23  ω   -119.00 -69.00   0.50    0.05    --  -42.30 169.00  12.00  100
 24  ω    -99.00 -32.00   0.50    0.05    -- -104.00 109.00 174.90  134
 25  ω   -126.00 -91.00   0.50    0.05    -- -104.00 144.00  95.01   70
 26  ω   -138.00 -78.00   0.50    0.05    -- -104.00 169.00  12.00  120
 27  ω    -84.00 -14.00   0.50    0.05    --  -42.30 114.00-130.00  140
 28  ω   -108.00 -74.00   0.50    0.05    -- -104.00 114.00-130.00   68
 29  ω    -66.00 -31.00   0.50    0.05    -- -104.00  61.00-150.00   70
 30  ω    -68.00 -43.00   0.50    0.05    -- -104.00  61.00-120.00   50
 31  ω    -68.00 -39.00   0.50    0.05    -- -104.00  61.00 -30.00   58
 32  ω    -68.00 -43.00   0.50    0.05    -- -104.00  61.00  90.00   50
 33  ω   -151.00 -56.00   0.50    0.05    -- -104.00 -15.00  60.00  190
 34  ω   -175.00 -89.00   0.50    0.05    -- -104.00 -45.00 150.00  172
 35  ω   -162.00-119.00   0.50    0.05    -- -104.00-114.00 139.00   86
 36  ω    -98.00 -58.00   0.50    0.05    -- -104.00-169.00  -4.00   80
 37  ω    -78.00 -46.00   0.50    0.05    --  -42.30-169.00  -4.00   64
 38  ω   -175.00 -83.00   0.50    0.05    -- -104.00 -45.00-150.00  184
 39  ω   -173.00-122.00   0.50    0.05    -- -104.00 -94.00-150.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0271351000
_diffrn_orient_matrix_UB_12      0.0647743000
_diffrn_orient_matrix_UB_13      0.1230697000
_diffrn_orient_matrix_UB_21      -0.1341329000
_diffrn_orient_matrix_UB_22      -0.0117174000
_diffrn_orient_matrix_UB_23      0.0092978000
_diffrn_orient_matrix_UB_31      -0.0042078000
_diffrn_orient_matrix_UB_32      -0.1223425000
_diffrn_orient_matrix_UB_33      0.0206401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6063
_reflns_number_total             6490
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.024
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         6490
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.053
_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)+(0.1030P)²+1.4994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1593
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C16-C17B \\sim C16-C17A
 with sigma of 0.02
 C17B-C18B \\sim C17A-C18A
 with sigma of 0.02
 C18B-C19B \\sim C18A-C19A
 with sigma of 0.02
 C19B-C20B \\sim C19A-C20A
 with sigma of 0.02
 C16-C18B \\sim C16-C18A
 with sigma of 0.04
 C17B-C19B \\sim C17A-C19A
 with sigma of 0.04
 C18B-C20B \\sim C18A-C20A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C20A \\sim C20B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C19A \\sim C19B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C18A \\sim C18B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
4. Others
 Sof(H16C)=Sof(H16D)=Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18C)=
 Sof(H18D)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=
 Sof(H20F)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(C17B)=Sof(H17A)=Sof(H17B)=Sof(C18B)=Sof(H18A)=
 Sof(H18B)=Sof(C19B)=Sof(H19A)=Sof(H19B)=Sof(C20B)=Sof(H20A)=Sof(H20B)=
 Sof(H20C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16(H16C,H16D), C11(H11A,H11B), C10(H10A,H10B), C12(H12A,
 H12B), C13(H13A,H13B), C17B(H17A,H17B), C18B(H18A,H18B), C19B(H19A,H19B),
 C17A(H17C,H17D), C18A(H18C,H18D), C19A(H19C,H19D)
5.b Aromatic/amide H refined with riding coordinates:
 C34(H34), C2(H2), C25(H25), C7(H7), C24(H24), C5(H5), C29(H29), C3(H3),
 C31(H31), C32(H32), C28(H28)
5.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C37(H37A,H37B,H37C), C14(H14A,H14B,H14C), C20B(H20A,H20B,
 H20C), C20A(H20D,H20E,H20F)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.46618(3) 0.25173(3) 0.96170(2) 0.04674(14) Uani 1 1 d . . . . .
O2 O 1.01684(16) 0.86395(18) 0.65668(16) 0.0380(4) Uani 1 1 d . . . . .
O1 O 0.10053(18) -0.32948(19) 0.27412(17) 0.0425(5) Uani 1 1 d . . . . .
H1 H 0.104415 -0.341181 0.207409 0.064 Uiso 1 1 calc R U . . .
N1 N 0.53971(18) 0.2637(2) 0.55909(17) 0.0297(4) Uani 1 1 d . . . . .
N2 N 0.39297(19) 0.0936(2) 0.53268(17) 0.0306(4) Uani 1 1 d . . . . .
N3 N 0.1029(3) -0.3676(3) 0.0511(2) 0.0525(7) Uani 1 1 d . . . . .
C36 C 0.4681(2) 0.1586(2) 0.4893(2) 0.0300(5) Uani 1 1 d . . . . .
C15 C 0.6270(2) 0.3169(3) 0.4067(2) 0.0327(5) Uani 1 1 d . . . . .
C34 C 0.4959(2) 0.2546(2) 0.7466(2) 0.0324(5) Uani 1 1 d . . . . .
H34 H 0.441253 0.179415 0.724059 0.039 Uiso 1 1 calc R U . . .
C21 C 0.6172(2) 0.3466(2) 0.5225(2) 0.0308(5) Uani 1 1 d . . . . .
C2 C 0.2397(2) -0.0805(2) 0.5101(2) 0.0342(5) Uani 1 1 d . . . . .
H2 H 0.234417 -0.055434 0.585971 0.041 Uiso 1 1 calc R U . . .
C35 C 0.5481(2) 0.3063(2) 0.6727(2) 0.0301(5) Uani 1 1 d . . . . .
C1 C 0.3223(2) -0.0095(2) 0.4653(2) 0.0313(5) Uani 1 1 d . . . . .
C8 C 0.4815(2) 0.1303(3) 0.3754(2) 0.0322(5) Uani 1 1 d . . . . .
C33 C 0.5288(2) 0.3200(3) 0.8557(2) 0.0350(5) Uani 1 1 d . . . . .
C26 C 0.9285(2) 0.7659(2) 0.6444(2) 0.0328(5) Uani 1 1 d . . . . .
C6 C 0.3280(2) -0.0488(2) 0.3514(2) 0.0330(5) Uani 1 1 d . . . . .
C25 C 0.9636(2) 0.6556(3) 0.6233(2) 0.0362(6) Uani 1 1 d . . . . .
H25 H 1.044804 0.652060 0.616855 0.043 Uiso 1 1 calc R U . . .
C22 C 0.6722(2) 0.4426(2) 0.6112(2) 0.0325(5) Uani 1 1 d . . . . .
C30 C 0.6291(2) 0.4179(2) 0.7057(2) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.4104(2) 0.0241(3) 0.3094(2) 0.0342(6) Uani 1 1 d . . . . .
H7 H 0.417314 -0.000417 0.233806 0.041 Uiso 1 1 calc R U . . .
C24 C 0.8816(2) 0.5511(3) 0.6116(2) 0.0361(6) Uani 1 1 d . . . . .
H24 H 0.907434 0.476719 0.598226 0.043 Uiso 1 1 calc R U . . .
C9 C 0.5635(2) 0.2126(3) 0.3367(2) 0.0343(6) Uani 1 1 d . . . . .
C16 C 0.7084(2) 0.4080(3) 0.3684(2) 0.0389(6) Uani 1 1 d D . . . .
H16A H 0.727888 0.367178 0.295224 0.047 Uiso 0.578(7) 1 calc R U P A 1
H16B H 0.783594 0.437353 0.418014 0.047 Uiso 0.578(7) 1 calc R U P A 1
H16C H 0.761028 0.367469 0.318715 0.047 Uiso 0.422(7) 1 calc R U P A 2
H16D H 0.758603 0.469929 0.431209 0.047 Uiso 0.422(7) 1 calc R U P A 2
C23 C 0.7606(2) 0.5528(2) 0.6191(2) 0.0332(5) Uani 1 1 d . . . . .
C4 C 0.1747(2) -0.2237(2) 0.3316(2) 0.0364(6) Uani 1 1 d . . . . .
C5 C 0.2526(2) -0.1568(3) 0.2861(2) 0.0357(6) Uani 1 1 d . . . . .
H5 H 0.256162 -0.183011 0.209915 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6766(2) 0.1025(3) 0.1928(2) 0.0398(6) Uani 1 1 d . . . . .
H11A H 0.751124 0.149183 0.239106 0.048 Uiso 1 1 calc R U . . .
H11B H 0.653249 0.027354 0.212080 0.048 Uiso 1 1 calc R U . . .
C29 C 0.7271(2) 0.6641(3) 0.6405(2) 0.0356(6) Uani 1 1 d . . . . .
H29 H 0.645931 0.667770 0.646834 0.043 Uiso 1 1 calc R U . . .
C3 C 0.1679(2) -0.1842(2) 0.4453(2) 0.0357(6) Uani 1 1 d . . . . .
H3 H 0.112804 -0.230636 0.476406 0.043 Uiso 1 1 calc R U . . .
C10 C 0.5790(2) 0.1766(3) 0.2169(2) 0.0378(6) Uani 1 1 d . . . . .
H10A H 0.599928 0.249921 0.194317 0.045 Uiso 1 1 calc R U . . .
H10B H 0.502978 0.128335 0.174161 0.045 Uiso 1 1 calc R U . . .
C31 C 0.6566(2) 0.4811(3) 0.8165(2) 0.0371(6) Uani 1 1 d . . . . .
H31 H 0.709197 0.557566 0.839685 0.045 Uiso 1 1 calc R U . . .
C32 C 0.6068(3) 0.4315(3) 0.8919(2) 0.0388(6) Uani 1 1 d . . . . .
H32 H 0.625373 0.473002 0.967371 0.047 Uiso 1 1 calc R U . . .
C28 C 0.8093(2) 0.7705(3) 0.6528(2) 0.0359(6) Uani 1 1 d . . . . .
H28 H 0.784057 0.845180 0.666688 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6999(2) 0.0700(3) 0.0736(2) 0.0408(6) Uani 1 1 d . . . . .
H12A H 0.627114 0.018590 0.027426 0.049 Uiso 1 1 calc R U . . .
H12B H 0.718303 0.144758 0.052752 0.049 Uiso 1 1 calc R U . . .
C27 C 0.9833(3) 0.9766(3) 0.6673(3) 0.0467(7) Uani 1 1 d . . . . .
H27A H 0.926766 0.968655 0.604735 0.070 Uiso 1 1 calc R U . . .
H27B H 1.053938 1.037826 0.670305 0.070 Uiso 1 1 calc R U . . .
H27C H 0.945933 1.001015 0.734172 0.070 Uiso 1 1 calc R U . . .
C13 C 0.8027(3) 0.0036(3) 0.0526(2) 0.0466(7) Uani 1 1 d . . . . .
H13A H 0.876435 0.056903 0.095678 0.056 Uiso 1 1 calc R U . . .
H13B H 0.786407 -0.068574 0.077493 0.056 Uiso 1 1 calc R U . . .
C37 C 0.0186(4) -0.3612(4) -0.1274(3) 0.0665(10) Uani 1 1 d . . . . .
H37A H -0.005962 -0.446130 -0.170893 0.100 Uiso 1 1 calc R U . . .
H37B H 0.088031 -0.323598 -0.154585 0.100 Uiso 1 1 calc R U . . .
H37C H -0.046744 -0.319303 -0.132620 0.100 Uiso 1 1 calc R U . . .
C14 C 0.8217(4) -0.0352(5) -0.0668(3) 0.0699(12) Uani 1 1 d . . . . .
H14A H 0.749628 -0.089487 -0.109619 0.105 Uiso 1 1 calc R U . . .
H14B H 0.888458 -0.077085 -0.076182 0.105 Uiso 1 1 calc R U . . .
H14C H 0.839413 0.036123 -0.091496 0.105 Uiso 1 1 calc R U . . .
C17B C 0.6529(4) 0.5217(5) 0.3634(5) 0.0295(11) Uani 0.578(7) 1 d D . P A 1
H17A H 0.577196 0.491903 0.314634 0.035 Uiso 0.578(7) 1 calc R U P A 1
H17B H 0.634073 0.562578 0.436872 0.035 Uiso 0.578(7) 1 calc R U P A 1
C38 C 0.0487(5) -0.3530(5) -0.0159(4) 0.0962(19) Uani 1 1 d . . . . .
C18B C 0.7309(8) 0.6124(8) 0.3248(8) 0.056(2) Uani 0.578(7) 1 d D U P A 1
H18A H 0.811352 0.629555 0.364538 0.067 Uiso 0.578(7) 1 calc R U P A 1
H18B H 0.700449 0.688151 0.346166 0.067 Uiso 0.578(7) 1 calc R U P A 1
C19B C 0.7434(5) 0.5813(6) 0.2060(5) 0.0491(15) Uani 0.578(7) 1 d D U P A 1
H19A H 0.662745 0.556027 0.165356 0.059 Uiso 0.578(7) 1 calc R U P A 1
H19B H 0.782350 0.511028 0.185805 0.059 Uiso 0.578(7) 1 calc R U P A 1
C20B C 0.8121(6) 0.6794(7) 0.1692(6) 0.065(2) Uani 0.578(7) 1 d D . P A 1
H20A H 0.824360 0.646676 0.092865 0.097 Uiso 0.578(7) 1 calc R U P A 1
H20B H 0.889276 0.711475 0.213761 0.097 Uiso 0.578(7) 1 calc R U P A 1
H20C H 0.767547 0.744181 0.176837 0.097 Uiso 0.578(7) 1 calc R U P A 1
C17A C 0.6296(5) 0.4664(6) 0.3095(6) 0.0282(14) Uani 0.422(7) 1 d D . P A 2
H17C H 0.566342 0.403404 0.259225 0.034 Uiso 0.422(7) 1 calc R U P A 2
H17D H 0.591198 0.522022 0.362921 0.034 Uiso 0.422(7) 1 calc R U P A 2
C18A C 0.7033(8) 0.5348(10) 0.2469(9) 0.069(3) Uani 0.422(7) 1 d D U P A 2
H18C H 0.655053 0.555902 0.192178 0.082 Uiso 0.422(7) 1 calc R U P A 2
H18D H 0.765602 0.493446 0.213104 0.082 Uiso 0.422(7) 1 calc R U P A 2
C19A C 0.7553(15) 0.6484(14) 0.3541(12) 0.077(3) Uani 0.422(7) 1 d D U P A 2
H19C H 0.686623 0.674636 0.389702 0.092 Uiso 0.422(7) 1 calc R U P A 2
H19D H 0.799996 0.618552 0.404848 0.092 Uiso 0.422(7) 1 calc R U P A 2
C20A C 0.8284(8) 0.7501(12) 0.3436(8) 0.096(5) Uani 0.422(7) 1 d D . P A 2
H20D H 0.890732 0.725697 0.298714 0.144 Uiso 0.422(7) 1 calc R U P A 2
H20E H 0.865008 0.802974 0.415652 0.144 Uiso 0.422(7) 1 calc R U P A 2
H20F H 0.781176 0.793337 0.309151 0.144 Uiso 0.422(7) 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 C33 1.902(3) . ?
O2 C26 1.366(3) . ?
O2 C27 1.424(4) . ?
O1 H1 0.8400 . ?
O1 C4 1.363(4) . ?
N1 C36 1.393(3) . ?
N1 C21 1.413(3) . ?
N1 C35 1.402(3) . ?
N2 C36 1.316(3) . ?
N2 C1 1.364(4) . ?
N3 C38 1.112(5) . ?
C36 C8 1.438(3) . ?
C15 C21 1.454(3) . ?
C15 C9 1.354(4) . ?
C15 C16 1.516(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.390(4) . ?
C34 C33 1.392(4) . ?
C21 C22 1.383(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.420(4) . ?
C2 C3 1.362(4) . ?
C35 C30 1.410(4) . ?
C1 C6 1.422(3) . ?
C8 C7 1.382(4) . ?
C8 C9 1.453(4) . ?
C33 C32 1.393(4) . ?
C26 C25 1.390(4) . ?
C26 C28 1.393(4) . ?
C6 C7 1.409(4) . ?
C6 C5 1.412(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.381(4) . ?
C22 C30 1.436(4) . ?
C22 C23 1.480(4) . ?
C30 C31 1.399(4) . ?
C7 H7 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.405(3) . ?
C9 C10 1.516(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 C17B 1.603(5) . ?
C16 C17A 1.527(6) . ?
C23 C29 1.392(4) . ?
C4 C5 1.366(4) . ?
C4 C3 1.421(4) . ?
C5 H5 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.535(4) . ?
C11 C12 1.531(3) . ?
C29 H29 0.9500 . ?
C29 C28 1.397(4) . ?
C3 H3 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C31 H31 0.9500 . ?
C31 C32 1.382(4) . ?
C32 H32 0.9500 . ?
C28 H28 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.527(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.522(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C37 C38 1.437(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C17B H17A 0.9900 . ?
C17B H17B 0.9900 . ?
C17B C18B 1.496(10) . ?
C18B H18A 0.9900 . ?
C18B H18B 0.9900 . ?
C18B C19B 1.498(11) . ?
C19B H19A 0.9900 . ?
C19B H19B 0.9900 . ?
C19B C20B 1.498(8) . ?
C20B H20A 0.9800 . ?
C20B H20B 0.9800 . ?
C20B H20C 0.9800 . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17A C18A 1.502(10) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C19A 1.621(14) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.388(15) . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 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
C26 O2 C27 117.7(2) . . ?
C4 O1 H1 109.5 . . ?
C36 N1 C21 123.2(2) . . ?
C36 N1 C35 128.0(2) . . ?
C35 N1 C21 108.8(2) . . ?
C36 N2 C1 118.0(2) . . ?
N1 C36 C8 117.4(2) . . ?
N2 C36 N1 117.3(2) . . ?
N2 C36 C8 125.2(2) . . ?
C21 C15 C16 117.4(2) . . ?
C9 C15 C21 120.6(2) . . ?
C9 C15 C16 122.0(2) . . ?
C35 C34 H34 122.2 . . ?
C35 C34 C33 115.7(3) . . ?
C33 C34 H34 122.2 . . ?
N1 C21 C15 118.0(2) . . ?
C22 C21 N1 108.9(2) . . ?
C22 C21 C15 133.0(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.7(2) . . ?
N1 C35 C30 106.7(2) . . ?
C34 C35 N1 130.9(2) . . ?
C34 C35 C30 122.4(2) . . ?
N2 C1 C2 119.0(2) . . ?
N2 C1 C6 122.5(2) . . ?
C2 C1 C6 118.5(2) . . ?
C36 C8 C9 120.0(2) . . ?
C7 C8 C36 115.5(2) . . ?
C7 C8 C9 124.5(2) . . ?
C34 C33 Br1 118.1(2) . . ?
C34 C33 C32 123.8(3) . . ?
C32 C33 Br1 118.0(2) . . ?
O2 C26 C25 116.0(2) . . ?
O2 C26 C28 124.5(2) . . ?
C25 C26 C28 119.5(3) . . ?
C7 C6 C1 117.1(2) . . ?
C7 C6 C5 123.2(2) . . ?
C5 C6 C1 119.7(2) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C21 C22 C30 106.8(2) . . ?
C21 C22 C23 131.4(2) . . ?
C30 C22 C23 121.8(2) . . ?
C35 C30 C22 108.8(2) . . ?
C31 C30 C35 119.4(2) . . ?
C31 C30 C22 131.8(3) . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C25 C24 H24 119.4 . . ?
C25 C24 C23 121.2(2) . . ?
C23 C24 H24 119.4 . . ?
C15 C9 C8 120.6(2) . . ?
C15 C9 C10 121.1(2) . . ?
C8 C9 C10 118.2(3) . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C15 C16 H16C 110.3 . . ?
C15 C16 H16D 110.3 . . ?
C15 C16 C17B 113.9(2) . . ?
C15 C16 C17A 107.2(3) . . ?
H16A C16 H16B 107.7 . . ?
H16C C16 H16D 108.5 . . ?
C17B C16 H16A 108.8 . . ?
C17B C16 H16B 108.8 . . ?
C17A C16 H16C 110.3 . . ?
C17A C16 H16D 110.3 . . ?
C24 C23 C22 121.9(2) . . ?
C29 C23 C22 120.5(2) . . ?
C29 C23 C24 117.4(3) . . ?
O1 C4 C5 123.8(3) . . ?
O1 C4 C3 116.1(3) . . ?
C5 C4 C3 120.1(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
H11A C11 H11B 107.8 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C12 C11 C10 112.9(2) . . ?
C23 C29 H29 119.0 . . ?
C23 C29 C28 121.9(2) . . ?
C28 C29 H29 119.0 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C9 C10 C11 111.2(2) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.5(3) . . ?
C32 C31 H31 120.3 . . ?
C33 C32 H32 120.4 . . ?
C31 C32 C33 119.1(3) . . ?
C31 C32 H32 120.4 . . ?
C26 C28 C29 119.3(2) . . ?
C26 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 C11 112.2(2) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
O2 C27 H27A 109.5 . . ?
O2 C27 H27B 109.5 . . ?
O2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C12 112.4(3) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C17B H17A 108.5 . . ?
C16 C17B H17B 108.5 . . ?
H17A C17B H17B 107.5 . . ?
C18B C17B C16 115.0(5) . . ?
C18B C17B H17A 108.5 . . ?
C18B C17B H17B 108.5 . . ?
N3 C38 C37 153.6(7) . . ?
C17B C18B H18A 107.8 . . ?
C17B C18B H18B 107.8 . . ?
C17B C18B C19B 117.9(7) . . ?
H18A C18B H18B 107.2 . . ?
C19B C18B H18A 107.8 . . ?
C19B C18B H18B 107.8 . . ?
C18B C19B H19A 108.3 . . ?
C18B C19B H19B 108.3 . . ?
C18B C19B C20B 116.1(6) . . ?
H19A C19B H19B 107.4 . . ?
C20B C19B H19A 108.3 . . ?
C20B C19B H19B 108.3 . . ?
C19B C20B H20A 109.5 . . ?
C19B C20B H20B 109.5 . . ?
C19B C20B H20C 109.5 . . ?
H20A C20B H20B 109.5 . . ?
H20A C20B H20C 109.5 . . ?
H20B C20B H20C 109.5 . . ?
C16 C17A H17C 109.7 . . ?
C16 C17A H17D 109.7 . . ?
H17C C17A H17D 108.2 . . ?
C18A C17A C16 109.7(5) . . ?
C18A C17A H17C 109.7 . . ?
C18A C17A H17D 109.7 . . ?
C17A C18A H18C 113.1 . . ?
C17A C18A H18D 113.1 . . ?
C17A C18A C19A 93.1(9) . . ?
H18C C18A H18D 110.5 . . ?
C19A C18A H18C 113.1 . . ?
C19A C18A H18D 113.1 . . ?
C18A C19A H19C 107.4 . . ?
C18A C19A H19D 107.4 . . ?
H19C C19A H19D 107.0 . . ?
C20A C19A C18A 119.5(11) . . ?
C20A C19A H19C 107.4 . . ?
C20A C19A H19D 107.4 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 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 C33 C32 C31 177.8(2) . . . . ?
O2 C26 C25 C24 178.8(2) . . . . ?
O2 C26 C28 C29 -178.9(2) . . . . ?
O1 C4 C5 C6 -179.0(2) . . . . ?
O1 C4 C3 C2 179.0(2) . . . . ?
N1 C36 C8 C7 178.8(2) . . . . ?
N1 C36 C8 C9 -2.7(3) . . . . ?
N1 C21 C22 C30 0.8(3) . . . . ?
N1 C21 C22 C23 179.8(2) . . . . ?
N1 C35 C30 C22 -1.0(3) . . . . ?
N1 C35 C30 C31 -179.0(2) . . . . ?
N2 C36 C8 C7 -1.7(3) . . . . ?
N2 C36 C8 C9 176.9(2) . . . . ?
N2 C1 C6 C7 -0.2(3) . . . . ?
N2 C1 C6 C5 179.8(2) . . . . ?
C36 N1 C21 C15 -3.6(3) . . . . ?
C36 N1 C21 C22 178.0(2) . . . . ?
C36 N1 C35 C34 4.8(4) . . . . ?
C36 N1 C35 C30 -177.9(2) . . . . ?
C36 N2 C1 C2 -179.3(2) . . . . ?
C36 N2 C1 C6 0.5(3) . . . . ?
C36 C8 C7 C6 1.9(3) . . . . ?
C36 C8 C9 C15 -0.6(3) . . . . ?
C36 C8 C9 C10 177.3(2) . . . . ?
C15 C21 C22 C30 -177.3(2) . . . . ?
C15 C21 C22 C23 1.7(4) . . . . ?
C15 C9 C10 C11 89.6(3) . . . . ?
C15 C16 C17B C18B -179.4(5) . . . . ?
C15 C16 C17A C18A -166.4(6) . . . . ?
C34 C35 C30 C22 176.5(2) . . . . ?
C34 C35 C30 C31 -1.5(4) . . . . ?
C34 C33 C32 C31 -0.9(4) . . . . ?
C21 N1 C36 N2 -174.8(2) . . . . ?
C21 N1 C36 C8 4.8(3) . . . . ?
C21 N1 C35 C34 -175.7(2) . . . . ?
C21 N1 C35 C30 1.5(2) . . . . ?
C21 C15 C9 C8 2.0(3) . . . . ?
C21 C15 C9 C10 -175.9(2) . . . . ?
C21 C15 C16 C17B -77.1(4) . . . . ?
C21 C15 C16 C17A -107.8(4) . . . . ?
C21 C22 C30 C35 0.1(3) . . . . ?
C21 C22 C30 C31 177.8(3) . . . . ?
C21 C22 C23 C24 -77.9(4) . . . . ?
C21 C22 C23 C29 105.7(3) . . . . ?
C2 C1 C6 C7 179.6(2) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C35 N1 C36 N2 4.6(3) . . . . ?
C35 N1 C36 C8 -175.8(2) . . . . ?
C35 N1 C21 C15 176.94(19) . . . . ?
C35 N1 C21 C22 -1.5(3) . . . . ?
C35 C34 C33 Br1 -177.40(17) . . . . ?
C35 C34 C33 C32 1.3(4) . . . . ?
C35 C30 C31 C32 1.9(4) . . . . ?
C1 N2 C36 N1 -180.0(2) . . . . ?
C1 N2 C36 C8 0.5(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C6 C7 C8 -1.1(3) . . . . ?
C1 C6 C5 C4 -0.2(4) . . . . ?
C8 C9 C10 C11 -88.3(3) . . . . ?
C33 C34 C35 N1 176.8(2) . . . . ?
C33 C34 C35 C30 -0.1(3) . . . . ?
C26 C25 C24 C23 0.9(4) . . . . ?
C25 C26 C28 C29 0.4(4) . . . . ?
C25 C24 C23 C22 -177.5(3) . . . . ?
C25 C24 C23 C29 -1.0(4) . . . . ?
C22 C30 C31 C32 -175.6(3) . . . . ?
C22 C23 C29 C28 177.4(3) . . . . ?
C30 C22 C23 C24 100.9(3) . . . . ?
C30 C22 C23 C29 -75.6(3) . . . . ?
C30 C31 C32 C33 -0.8(4) . . . . ?
C7 C8 C9 C15 177.8(2) . . . . ?
C7 C8 C9 C10 -4.3(4) . . . . ?
C7 C6 C5 C4 179.9(2) . . . . ?
C24 C23 C29 C28 0.8(4) . . . . ?
C9 C15 C21 N1 0.0(3) . . . . ?
C9 C15 C21 C22 178.0(2) . . . . ?
C9 C15 C16 C17B 101.6(4) . . . . ?
C9 C15 C16 C17A 70.9(4) . . . . ?
C9 C8 C7 C6 -176.6(2) . . . . ?
C16 C15 C21 N1 178.73(19) . . . . ?
C16 C15 C21 C22 -3.3(4) . . . . ?
C16 C15 C9 C8 -176.7(2) . . . . ?
C16 C15 C9 C10 5.4(4) . . . . ?
C16 C17B C18B C19B 75.0(8) . . . . ?
C16 C17A C18A C19A -78.7(10) . . . . ?
C23 C22 C30 C35 -179.0(2) . . . . ?
C23 C22 C30 C31 -1.2(4) . . . . ?
C23 C29 C28 C26 -0.5(4) . . . . ?
C5 C6 C7 C8 178.9(2) . . . . ?
C5 C4 C3 C2 -0.8(4) . . . . ?
C11 C12 C13 C14 176.8(3) . . . . ?
C3 C2 C1 N2 -179.8(2) . . . . ?
C3 C2 C1 C6 0.3(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C10 C11 C12 C13 176.3(3) . . . . ?
C28 C26 C25 C24 -0.6(4) . . . . ?
C12 C11 C10 C9 -176.8(3) . . . . ?
C27 O2 C26 C25 173.7(3) . . . . ?
C27 O2 C26 C28 -6.9(4) . . . . ?
C17B C18B C19B C20B 174.0(6) . . . . ?
C17A C18A C19A C20A -175.8(14) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 5.906
_oxdiff_exptl_absorpt_empirical_full_min 0.535
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_preparation       Luminescent
