# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_11
_audit_block_doi                 10.5517/ccdc.csd.cc2r9hwg
_database_code_depnum_ccdc_archive 'CCDC 2541376'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.15003255/v1 2026
loop_
_audit_author_name
_audit_author_address
'shiwu lishiwuabcd'
;Shihezi University
China
;
_audit_update_record             
;
2026-03-26 deposited with the CCDC.	2026-06-05 downloaded from the CCDC.
;
_audit_creation_date             2025-02-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N'
_chemical_formula_sum            'C26 H21 N'
_chemical_formula_weight         347.44
_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 0.0181 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'
N N 0.0311 0.0180 '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                   8.5087(14)
_cell_length_b                   9.0486(15)
_cell_length_c                   13.346(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.010(8)
_cell_angle_gamma                90
_cell_volume                     992.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5435
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      74.41
_cell_measurement_theta_min      3.43
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1452 before and 0.0686 after correction.
The Ratio of minimum to maximum transmission is 0.8822.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14515
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.873
_diffrn_reflns_theta_min         3.428
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3100
_reflns_number_total             3959
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 
;
 Flack x determined using 1128 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       0.032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.041
_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)+(0.0418P)²+0.0919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1102
_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:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
2.d :
 C1(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
C1 C 0.5578(4) 0.6663(5) 0.0536(3) 0.0958(12) Uani 1 1 d . . . . .
H1 H 0.634647 0.661325 0.015200 0.115 Uiso 1 1 calc R U . . .
C2 C 0.4611(4) 0.6725(3) 0.1019(2) 0.0661(7) Uani 1 1 d . . . . .
C3 C 0.3453(3) 0.6826(3) 0.1626(2) 0.0555(6) Uani 1 1 d . . . . .
C4 C 0.1979(3) 0.7651(3) 0.1222(2) 0.0634(7) Uani 1 1 d . . . . .
C5 C 0.1619(4) 0.8351(4) 0.0245(3) 0.0815(9) Uani 1 1 d . . . . .
H5 H 0.234945 0.829982 -0.016560 0.098 Uiso 1 1 calc R U . . .
C6 C 0.0177(6) 0.9112(5) -0.0097(4) 0.1031(13) Uani 1 1 d . . . . .
H6 H -0.005650 0.957229 -0.074179 0.124 Uiso 1 1 calc R U . . .
C7 C -0.0924(5) 0.9205(5) 0.0494(4) 0.1102(14) Uani 1 1 d . . . . .
H7 H -0.189052 0.972295 0.024528 0.132 Uiso 1 1 calc R U . . .
C8 C -0.0614(4) 0.8555(4) 0.1425(4) 0.0942(12) Uani 1 1 d . . . . .
H8 H -0.137331 0.862314 0.181450 0.113 Uiso 1 1 calc R U . . .
C9 C 0.0859(4) 0.7760(3) 0.1830(3) 0.0702(8) Uani 1 1 d . . . . .
C10 C 0.1223(4) 0.7083(4) 0.2810(3) 0.0775(9) Uani 1 1 d . . . . .
H10 H 0.048764 0.715696 0.321544 0.093 Uiso 1 1 calc R U . . .
C11 C 0.2630(4) 0.6323(4) 0.3176(2) 0.0696(7) Uani 1 1 d . . . . .
H11 H 0.284453 0.589461 0.383045 0.083 Uiso 1 1 calc R U . . .
C12 C 0.3767(3) 0.6170(3) 0.2588(2) 0.0549(6) Uani 1 1 d . . . . .
C13 C 0.5318(3) 0.5278(3) 0.29870(19) 0.0563(6) Uani 1 1 d . . . . .
H13 H 0.614079 0.574070 0.269363 0.068 Uiso 1 1 calc R U . . .
C14 C 0.5152(3) 0.3690(3) 0.2596(2) 0.0639(7) Uani 1 1 d . . . . .
C15 C 0.3711(4) 0.2922(4) 0.2362(3) 0.0777(9) Uani 1 1 d . . . . .
H15 H 0.276070 0.339628 0.240474 0.093 Uiso 1 1 calc R U . . .
C16 C 0.3648(6) 0.1450(4) 0.2063(3) 0.0950(11) Uani 1 1 d . . . . .
H16 H 0.266488 0.094228 0.191908 0.114 Uiso 1 1 calc R U . . .
C17 C 0.5028(6) 0.0747(4) 0.1978(3) 0.1063(14) Uani 1 1 d . . . . .
H17 H 0.499363 -0.024346 0.178780 0.128 Uiso 1 1 calc R U . . .
C18 C 0.6456(6) 0.1511(5) 0.2176(4) 0.1165(16) Uani 1 1 d . . . . .
H18 H 0.739404 0.103975 0.210679 0.140 Uiso 1 1 calc R U . . .
C19 C 0.6529(4) 0.2976(4) 0.2477(3) 0.0928(11) Uani 1 1 d . . . . .
H19 H 0.751019 0.348505 0.260120 0.111 Uiso 1 1 calc R U . . .
C20 C 0.7081(3) 0.6434(3) 0.4543(2) 0.0561(6) Uani 1 1 d . . . . .
C21 C 0.7282(3) 0.7704(3) 0.3993(2) 0.0654(7) Uani 1 1 d . . . . .
H21 H 0.664584 0.783419 0.331837 0.079 Uiso 1 1 calc R U . . .
C22 C 0.8415(4) 0.8771(4) 0.4438(3) 0.0812(9) Uani 1 1 d . . . . .
H22 H 0.853207 0.960408 0.405582 0.097 Uiso 1 1 calc R U . . .
C23 C 0.9363(4) 0.8620(4) 0.5428(3) 0.0888(11) Uani 1 1 d . . . . .
H23 H 1.013795 0.933001 0.571622 0.107 Uiso 1 1 calc R U . . .
C24 C 0.9151(4) 0.7404(5) 0.5987(3) 0.0851(10) Uani 1 1 d . . . . .
H24 H 0.976988 0.730954 0.666906 0.102 Uiso 1 1 calc R U . . .
C25 C 0.8039(3) 0.6311(4) 0.5564(2) 0.0689(8) Uani 1 1 d . . . . .
H25 H 0.792769 0.549087 0.595992 0.083 Uiso 1 1 calc R U . . .
C26 C 0.5643(5) 0.4160(4) 0.4760(3) 0.0911(11) Uani 1 1 d . . . . .
H26A H 0.655699 0.349996 0.492586 0.137 Uiso 1 1 calc R U . . .
H26B H 0.468908 0.362899 0.439595 0.137 Uiso 1 1 calc R U . . .
H26C H 0.547147 0.456461 0.538842 0.137 Uiso 1 1 calc R U . . .
N1 N 0.5960(3) 0.5343(3) 0.41139(17) 0.0654(6) Uani 1 1 d . . . . .


_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
C1 H1 0.9300 . ?
C1 C2 1.171(4) . ?
C2 C3 1.432(4) . ?
C3 C4 1.438(4) . ?
C3 C12 1.376(4) . ?
C4 C5 1.411(4) . ?
C4 C9 1.406(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.338(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.425(4) . ?
C9 C10 1.404(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.357(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.401(4) . ?
C12 C13 1.521(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.523(4) . ?
C13 N1 1.462(3) . ?
C14 C15 1.373(4) . ?
C14 C19 1.382(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.366(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.363(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.398(4) . ?
C20 C25 1.399(4) . ?
C20 N1 1.389(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.365(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.367(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(4) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 N1 1.444(4) . ?

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
C2 C1 H1 180.0 . . ?
C1 C2 C3 178.7(4) . . ?
C2 C3 C4 118.8(2) . . ?
C12 C3 C2 120.3(2) . . ?
C12 C3 C4 120.9(2) . . ?
C5 C4 C3 122.6(3) . . ?
C9 C4 C3 118.4(3) . . ?
C9 C4 C5 119.0(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.1(4) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 118.6(3) . . ?
C10 C9 C4 119.2(3) . . ?
C10 C9 C8 122.3(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C3 C12 C11 119.0(2) . . ?
C3 C12 C13 119.8(2) . . ?
C11 C12 C13 121.2(2) . . ?
C12 C13 H13 106.2 . . ?
C12 C13 C14 112.7(2) . . ?
C14 C13 H13 106.2 . . ?
N1 C13 C12 113.5(2) . . ?
N1 C13 H13 106.2 . . ?
N1 C13 C14 111.6(2) . . ?
C15 C14 C13 123.6(3) . . ?
C15 C14 C19 118.1(3) . . ?
C19 C14 C13 118.3(3) . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.9(4) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 120.4(4) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C25 117.2(2) . . ?
N1 C20 C21 122.1(2) . . ?
N1 C20 C25 120.6(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 120.6 . . ?
C22 C23 C24 118.7(3) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 H24 119.2 . . ?
C23 C24 C25 121.7(3) . . ?
C25 C24 H24 119.2 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.3(3) . . ?
C24 C25 H25 119.8 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
C20 N1 C13 119.1(2) . . ?
C20 N1 C26 119.7(2) . . ?
C26 N1 C13 120.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 0.8(4) . . . . ?
C2 C3 C4 C9 -179.2(3) . . . . ?
C2 C3 C12 C11 178.2(3) . . . . ?
C2 C3 C12 C13 -2.7(4) . . . . ?
C3 C4 C5 C6 179.4(3) . . . . ?
C3 C4 C9 C8 -179.0(3) . . . . ?
C3 C4 C9 C10 0.9(4) . . . . ?
C3 C12 C13 C14 -84.1(3) . . . . ?
C3 C12 C13 N1 147.9(2) . . . . ?
C4 C3 C12 C11 -0.3(4) . . . . ?
C4 C3 C12 C13 178.8(2) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C4 C9 C10 C11 -0.3(5) . . . . ?
C5 C4 C9 C8 1.1(4) . . . . ?
C5 C4 C9 C10 -179.1(3) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C6 C7 C8 C9 0.3(7) . . . . ?
C7 C8 C9 C4 -1.0(5) . . . . ?
C7 C8 C9 C10 179.2(4) . . . . ?
C8 C9 C10 C11 179.5(3) . . . . ?
C9 C4 C5 C6 -0.6(5) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C3 1.0(4) . . . . ?
C10 C11 C12 C13 -178.1(3) . . . . ?
C11 C12 C13 C14 95.0(3) . . . . ?
C11 C12 C13 N1 -33.0(4) . . . . ?
C12 C3 C4 C5 179.4(3) . . . . ?
C12 C3 C4 C9 -0.6(4) . . . . ?
C12 C13 C14 C15 -29.7(4) . . . . ?
C12 C13 C14 C19 150.8(3) . . . . ?
C12 C13 N1 C20 -91.0(3) . . . . ?
C12 C13 N1 C26 98.8(3) . . . . ?
C13 C14 C15 C16 -176.4(3) . . . . ?
C13 C14 C19 C18 176.7(3) . . . . ?
C14 C13 N1 C20 140.4(3) . . . . ?
C14 C13 N1 C26 -29.7(4) . . . . ?
C14 C15 C16 C17 -1.2(6) . . . . ?
C15 C14 C19 C18 -2.8(5) . . . . ?
C15 C16 C17 C18 -1.0(6) . . . . ?
C16 C17 C18 C19 1.2(7) . . . . ?
C17 C18 C19 C14 0.8(7) . . . . ?
C19 C14 C15 C16 3.0(5) . . . . ?
C20 C21 C22 C23 -0.4(5) . . . . ?
C21 C20 C25 C24 -1.1(4) . . . . ?
C21 C20 N1 C13 18.4(4) . . . . ?
C21 C20 N1 C26 -171.4(3) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C22 C23 C24 C25 1.9(5) . . . . ?
C23 C24 C25 C20 -0.6(5) . . . . ?
C25 C20 C21 C22 1.6(4) . . . . ?
C25 C20 N1 C13 -162.9(2) . . . . ?
C25 C20 N1 C26 7.3(4) . . . . ?
N1 C13 C14 C15 99.3(3) . . . . ?
N1 C13 C14 C19 -80.2(3) . . . . ?
N1 C20 C21 C22 -179.7(3) . . . . ?
N1 C20 C25 C24 -179.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2r9htd
_database_code_depnum_ccdc_archive 'CCDC 2541374'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.15003255/v1 2026
loop_
_audit_author_name
_audit_author_address
'shiwu lishiwuabcd'
;Shihezi University
China
;
_audit_update_record             
;
2026-03-26 deposited with the CCDC.	2026-06-05 downloaded from the CCDC.
;
_audit_creation_date             2025-05-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H19 N O'
_chemical_formula_sum            'C26 H19 N O'
_chemical_formula_weight         361.42
_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 0.0181 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'
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                   9.2110(9)
_cell_length_b                   9.3934(9)
_cell_length_c                   22.180(2)
_cell_angle_alpha                87.203(4)
_cell_angle_beta                 80.528(4)
_cell_angle_gamma                84.782(4)
_cell_volume                     1884.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9469
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      4.88
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0954 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.8684.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18311
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.320
_diffrn_reflns_theta_min         2.021
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5419
_reflns_number_total             6773
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         6773
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.056
_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)+(0.0573P)²+0.6411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1343
_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 Riding coordinates:
 C52(H52A,H52B,H52C)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25),
  C27(H27), C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37),
 C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48), C50(H50),
  C51(H51)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_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
C1 C 0.7012(2) 0.7519(2) -0.09514(9) 0.0407(4) Uani 1 1 d . . . . .
H1 H 0.781528 0.772014 -0.075899 0.049 Uiso 1 1 calc R U . . .
C2 C 0.5613(2) 0.74141(19) -0.05603(8) 0.0357(4) Uani 1 1 d . . . . .
C3 C 0.4202(2) 0.70308(18) -0.06342(8) 0.0348(4) Uani 1 1 d . . . . .
C4 C 0.3494(2) 0.69002(19) -0.11638(9) 0.0382(4) Uani 1 1 d . . . . .
C5 C 0.4191(2) 0.7113(2) -0.17733(9) 0.0455(5) Uani 1 1 d . . . . .
H5 H 0.519821 0.731294 -0.185519 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3413(3) 0.7033(2) -0.22532(10) 0.0522(5) Uani 1 1 d . . . . .
H6 H 0.389186 0.718462 -0.266149 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1940(3) 0.6732(2) -0.21445(11) 0.0543(6) Uani 1 1 d . . . . .
H7 H 0.141868 0.667676 -0.247703 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1243(2) 0.6517(2) -0.15556(10) 0.0477(5) Uani 1 1 d . . . . .
H8 H 0.023810 0.630665 -0.148503 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1985(2) 0.6601(2) -0.10534(9) 0.0402(4) Uani 1 1 d . . . . .
C10 C 0.1218(2) 0.6401(2) -0.04391(10) 0.0421(4) Uani 1 1 d . . . . .
H10 H 0.022055 0.617039 -0.037959 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1874(2) 0.6533(2) 0.00568(9) 0.0399(4) Uani 1 1 d . . . . .
H11 H 0.134484 0.640449 0.045829 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3380(2) 0.68694(19) -0.00367(8) 0.0355(4) Uani 1 1 d . . . . .
C13 C 0.4246(2) 0.72077(19) 0.03904(8) 0.0348(4) Uani 1 1 d . . . . .
C14 C 0.3813(2) 0.7377(2) 0.10566(8) 0.0374(4) Uani 1 1 d . . . . .
C15 C 0.3118(2) 0.6301(2) 0.14166(10) 0.0473(5) Uani 1 1 d . . . . .
H15 H 0.297523 0.543457 0.123918 0.057 Uiso 1 1 calc R U . . .
C16 C 0.2632(3) 0.6501(3) 0.20373(10) 0.0565(6) Uani 1 1 d . . . . .
H16 H 0.215277 0.576641 0.228068 0.068 Uiso 1 1 calc R U . . .
C17 C 0.2836(3) 0.7747(3) 0.23046(10) 0.0541(6) Uani 1 1 d . . . . .
H17 H 0.249209 0.787330 0.272798 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3544(2) 0.8812(2) 0.19523(9) 0.0474(5) Uani 1 1 d . . . . .
H18 H 0.370189 0.966660 0.213514 0.057 Uiso 1 1 calc R U . . .
C19 C 0.4023(2) 0.8635(2) 0.13324(9) 0.0399(4) Uani 1 1 d . . . . .
H19 H 0.449904 0.937536 0.109224 0.048 Uiso 1 1 calc R U . . .
C20 C 0.6758(2) 0.79744(19) 0.03534(8) 0.0340(4) Uani 1 1 d . . . . .
C21 C 0.7221(2) 0.93355(19) 0.02287(9) 0.0381(4) Uani 1 1 d . . . . .
H21 H 0.679329 0.996234 -0.005555 0.046 Uiso 1 1 calc R U . . .
C22 C 0.8309(2) 0.9775(2) 0.05206(9) 0.0401(4) Uani 1 1 d . . . . .
H22 H 0.863539 1.070302 0.042937 0.048 Uiso 1 1 calc R U . . .
C23 C 0.8935(2) 0.8885(2) 0.09450(9) 0.0388(4) Uani 1 1 d . . . . .
C24 C 0.8452(2) 0.7520(2) 0.10573(9) 0.0389(4) Uani 1 1 d . . . . .
H24 H 0.887879 0.688844 0.134027 0.047 Uiso 1 1 calc R U . . .
C25 C 0.7371(2) 0.70605(19) 0.07685(9) 0.0366(4) Uani 1 1 d . . . . .
H25 H 0.705230 0.612750 0.085390 0.044 Uiso 1 1 calc R U . . .
C26 C 1.0085(2) 0.9406(3) 0.12704(11) 0.0520(5) Uani 1 1 d . . . . .
H26A H 1.086281 0.979812 0.096971 0.078 Uiso 1 1 calc R U . . .
H26B H 1.051487 0.860750 0.150239 0.078 Uiso 1 1 calc R U . . .
H26C H 0.962566 1.015342 0.155090 0.078 Uiso 1 1 calc R U . . .
N1 N 0.55733(17) 0.75362(16) 0.00733(7) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.72800(17) 0.73762(18) -0.15065(7) 0.0548(4) Uani 1 1 d . . . . .
C27 C 0.7915(2) 0.3290(2) 0.56981(8) 0.0367(4) Uani 1 1 d . . . . .
H27 H 0.779289 0.242651 0.551323 0.044 Uiso 1 1 calc R U . . .
C28 C 0.78206(19) 0.45765(19) 0.53236(8) 0.0323(4) Uani 1 1 d . . . . .
C29 C 0.81263(18) 0.60122(19) 0.53786(8) 0.0316(4) Uani 1 1 d . . . . .
C30 C 0.82911(19) 0.68528(19) 0.58900(8) 0.0339(4) Uani 1 1 d . . . . .
C31 C 0.8182(2) 0.6329(2) 0.65003(9) 0.0404(4) Uani 1 1 d . . . . .
H31 H 0.802881 0.535007 0.659216 0.048 Uiso 1 1 calc R U . . .
C32 C 0.8294(2) 0.7212(2) 0.69677(9) 0.0461(5) Uani 1 1 d . . . . .
H32 H 0.821524 0.683736 0.737639 0.055 Uiso 1 1 calc R U . . .
C33 C 0.8522(2) 0.8655(2) 0.68413(10) 0.0457(5) Uani 1 1 d . . . . .
H33 H 0.860772 0.925634 0.716354 0.055 Uiso 1 1 calc R U . . .
C34 C 0.8622(2) 0.9201(2) 0.62541(10) 0.0421(5) Uani 1 1 d . . . . .
H34 H 0.877394 1.018373 0.617430 0.050 Uiso 1 1 calc R U . . .
C35 C 0.85036(19) 0.8338(2) 0.57653(9) 0.0359(4) Uani 1 1 d . . . . .
C36 C 0.8556(2) 0.8945(2) 0.51560(9) 0.0378(4) Uani 1 1 d . . . . .
H36 H 0.871424 0.992889 0.508500 0.045 Uiso 1 1 calc R U . . .
C37 C 0.8388(2) 0.8162(2) 0.46792(9) 0.0364(4) Uani 1 1 d . . . . .
H37 H 0.842366 0.858672 0.428012 0.044 Uiso 1 1 calc R U . . .
C38 C 0.81572(19) 0.66844(19) 0.47895(8) 0.0328(4) Uani 1 1 d . . . . .
C39 C 0.78060(19) 0.56997(19) 0.43915(8) 0.0327(4) Uani 1 1 d . . . . .
C40 C 0.7479(2) 0.59776(19) 0.37648(8) 0.0343(4) Uani 1 1 d . . . . .
C41 C 0.8500(2) 0.6626(2) 0.33253(9) 0.0412(4) Uani 1 1 d . . . . .
H41 H 0.943465 0.680700 0.341905 0.049 Uiso 1 1 calc R U . . .
C42 C 0.8146(2) 0.7005(2) 0.27508(9) 0.0488(5) Uani 1 1 d . . . . .
H42 H 0.884285 0.744269 0.245167 0.059 Uiso 1 1 calc R U . . .
C43 C 0.6788(2) 0.6752(2) 0.26114(9) 0.0490(5) Uani 1 1 d . . . . .
H43 H 0.654612 0.702731 0.221977 0.059 Uiso 1 1 calc R U . . .
C44 C 0.5781(2) 0.6096(2) 0.30426(9) 0.0445(5) Uani 1 1 d . . . . .
H44 H 0.485330 0.590674 0.294419 0.053 Uiso 1 1 calc R U . . .
C45 C 0.6119(2) 0.5713(2) 0.36175(9) 0.0370(4) Uani 1 1 d . . . . .
H45 H 0.541866 0.526801 0.391273 0.044 Uiso 1 1 calc R U . . .
C46 C 0.71203(19) 0.32065(18) 0.44732(8) 0.0322(4) Uani 1 1 d . . . . .
C47 C 0.5791(2) 0.2696(2) 0.47382(9) 0.0378(4) Uani 1 1 d . . . . .
H47 H 0.523222 0.312119 0.509256 0.045 Uiso 1 1 calc R U . . .
C48 C 0.5282(2) 0.1558(2) 0.44822(10) 0.0420(5) Uani 1 1 d . . . . .
H48 H 0.437695 0.120044 0.466793 0.050 Uiso 1 1 calc R U . . .
C49 C 0.6071(2) 0.0930(2) 0.39586(9) 0.0394(4) Uani 1 1 d . . . . .
C50 C 0.7408(2) 0.1454(2) 0.37063(9) 0.0376(4) Uani 1 1 d . . . . .
H50 H 0.796920 0.102942 0.335229 0.045 Uiso 1 1 calc R U . . .
C51 C 0.7946(2) 0.25885(19) 0.39605(8) 0.0352(4) Uani 1 1 d . . . . .
H51 H 0.886519 0.293089 0.378365 0.042 Uiso 1 1 calc R U . . .
C52 C 0.5474(3) -0.0267(2) 0.36732(12) 0.0556(6) Uani 1 1 d . . . . .
H52A H 0.532944 0.002975 0.325590 0.083 Uiso 1 1 d R U . . .
H52B H 0.617594 -0.111785 0.366120 0.083 Uiso 1 1 d R U . . .
H52C H 0.452684 -0.048875 0.391500 0.083 Uiso 1 1 d R U . . .
N2 N 0.76030(16) 0.44470(15) 0.47169(7) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.81347(16) 0.31806(15) 0.62289(6) 0.0447(3) Uani 1 1 d . . . . .


_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
C1 H1 0.9500 . ?
C1 C2 1.439(3) . ?
C1 O1 1.227(2) . ?
C2 C3 1.417(3) . ?
C2 N1 1.410(2) . ?
C3 C4 1.449(3) . ?
C3 C12 1.422(3) . ?
C4 C5 1.411(3) . ?
C4 C9 1.422(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.409(3) . ?
C9 C10 1.440(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.355(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.431(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.478(3) . ?
C13 N1 1.360(2) . ?
C14 C15 1.393(3) . ?
C14 C19 1.399(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 C25 1.382(3) . ?
C20 N1 1.441(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(3) . ?
C23 C24 1.393(3) . ?
C23 C26 1.504(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.380(3) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27 0.9500 . ?
C27 C28 1.437(3) . ?
C27 O2 1.225(2) . ?
C28 C29 1.418(3) . ?
C28 N2 1.405(2) . ?
C29 C30 1.449(2) . ?
C29 C38 1.420(2) . ?
C30 C31 1.409(3) . ?
C30 C35 1.434(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.381(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.398(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.368(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.409(3) . ?
C35 C36 1.436(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.354(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.426(3) . ?
C38 C39 1.403(3) . ?
C39 C40 1.476(2) . ?
C39 N2 1.361(2) . ?
C40 C41 1.396(3) . ?
C40 C45 1.392(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.389(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.380(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.381(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.385(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.385(3) . ?
C46 C51 1.381(2) . ?
C46 N2 1.443(2) . ?
C47 H47 0.9500 . ?
C47 C48 1.386(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.391(3) . ?
C49 C50 1.388(3) . ?
C49 C52 1.505(3) . ?
C50 H50 0.9500 . ?
C50 C51 1.395(3) . ?
C51 H51 0.9500 . ?
C52 H52A 0.9801 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9799 . ?

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
C2 C1 H1 116.5 . . ?
O1 C1 H1 116.5 . . ?
O1 C1 C2 127.03(19) . . ?
C3 C2 C1 135.63(18) . . ?
N1 C2 C1 117.50(17) . . ?
N1 C2 C3 106.34(16) . . ?
C2 C3 C4 133.39(18) . . ?
C2 C3 C12 106.67(16) . . ?
C12 C3 C4 119.75(18) . . ?
C5 C4 C3 124.00(19) . . ?
C5 C4 C9 118.74(18) . . ?
C9 C4 C3 117.20(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C10 120.82(18) . . ?
C8 C9 C4 118.92(19) . . ?
C8 C9 C10 120.3(2) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.08(19) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.62(18) . . ?
C12 C11 H11 120.7 . . ?
C3 C12 C11 121.49(18) . . ?
C13 C12 C3 108.79(17) . . ?
C13 C12 C11 129.51(18) . . ?
C12 C13 C14 128.75(17) . . ?
N1 C13 C12 107.30(16) . . ?
N1 C13 C14 123.54(17) . . ?
C15 C14 C13 119.91(18) . . ?
C15 C14 C19 118.79(18) . . ?
C19 C14 C13 121.22(18) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C21 C20 N1 119.72(16) . . ?
C25 C20 C21 120.50(18) . . ?
C25 C20 N1 119.70(17) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.51(17) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.30(18) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 117.78(18) . . ?
C22 C23 C26 120.20(19) . . ?
C24 C23 C26 122.02(18) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.74(17) . . ?
C25 C24 H24 119.1 . . ?
C20 C25 H25 120.4 . . ?
C24 C25 C20 119.17(18) . . ?
C24 C25 H25 120.4 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2 N1 C20 125.20(15) . . ?
C13 N1 C2 110.84(16) . . ?
C13 N1 C20 123.96(15) . . ?
C28 C27 H27 116.3 . . ?
O2 C27 H27 116.3 . . ?
O2 C27 C28 127.33(18) . . ?
C29 C28 C27 134.85(17) . . ?
N2 C28 C27 117.72(16) . . ?
N2 C28 C29 106.57(15) . . ?
C28 C29 C30 133.74(17) . . ?
C28 C29 C38 106.67(15) . . ?
C38 C29 C30 119.43(16) . . ?
C31 C30 C29 124.56(17) . . ?
C31 C30 C35 118.24(17) . . ?
C35 C30 C29 117.12(17) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.2(2) . . ?
C32 C31 H31 119.4 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.2(2) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.07(19) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 119.3 . . ?
C33 C34 C35 121.44(19) . . ?
C35 C34 H34 119.3 . . ?
C30 C35 C36 120.66(17) . . ?
C34 C35 C30 118.80(18) . . ?
C34 C35 C36 120.51(18) . . ?
C35 C36 H36 118.9 . . ?
C37 C36 C35 122.17(18) . . ?
C37 C36 H36 118.9 . . ?
C36 C37 H37 120.7 . . ?
C36 C37 C38 118.55(18) . . ?
C38 C37 H37 120.7 . . ?
C29 C38 C37 122.04(17) . . ?
C39 C38 C29 108.63(16) . . ?
C39 C38 C37 129.11(17) . . ?
C38 C39 C40 127.83(16) . . ?
N2 C39 C38 107.33(15) . . ?
N2 C39 C40 124.24(16) . . ?
C41 C40 C39 119.54(18) . . ?
C45 C40 C39 121.02(17) . . ?
C45 C40 C41 119.22(17) . . ?
C40 C41 H41 120.1 . . ?
C42 C41 C40 119.9(2) . . ?
C42 C41 H41 120.1 . . ?
C41 C42 H42 119.8 . . ?
C43 C42 C41 120.5(2) . . ?
C43 C42 H42 119.8 . . ?
C42 C43 H43 120.1 . . ?
C42 C43 C44 119.86(19) . . ?
C44 C43 H43 120.1 . . ?
C43 C44 H44 119.9 . . ?
C43 C44 C45 120.3(2) . . ?
C45 C44 H44 119.9 . . ?
C40 C45 H45 119.9 . . ?
C44 C45 C40 120.28(19) . . ?
C44 C45 H45 119.9 . . ?
C47 C46 N2 119.37(15) . . ?
C51 C46 C47 120.71(17) . . ?
C51 C46 N2 119.83(16) . . ?
C46 C47 H47 120.3 . . ?
C46 C47 C48 119.45(17) . . ?
C48 C47 H47 120.3 . . ?
C47 C48 H48 119.3 . . ?
C47 C48 C49 121.31(19) . . ?
C49 C48 H48 119.3 . . ?
C48 C49 C52 120.57(19) . . ?
C50 C49 C48 118.01(18) . . ?
C50 C49 C52 121.42(18) . . ?
C49 C50 H50 119.2 . . ?
C49 C50 C51 121.55(17) . . ?
C51 C50 H50 119.2 . . ?
C46 C51 C50 118.95(18) . . ?
C46 C51 H51 120.5 . . ?
C50 C51 H51 120.5 . . ?
C49 C52 H52A 109.2 . . ?
C49 C52 H52B 109.6 . . ?
C49 C52 H52C 109.6 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C28 N2 C46 125.60(15) . . ?
C39 N2 C28 110.71(15) . . ?
C39 N2 C46 123.53(15) . . ?

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
C1 C2 C3 C4 -16.9(4) . . . . ?
C1 C2 C3 C12 168.3(2) . . . . ?
C1 C2 N1 C13 -170.99(16) . . . . ?
C1 C2 N1 C20 10.1(3) . . . . ?
C2 C3 C4 C5 2.4(3) . . . . ?
C2 C3 C4 C9 -174.67(18) . . . . ?
C2 C3 C12 C11 177.68(16) . . . . ?
C2 C3 C12 C13 2.54(19) . . . . ?
C3 C2 N1 C13 1.94(19) . . . . ?
C3 C2 N1 C20 -176.96(15) . . . . ?
C3 C4 C5 C6 -176.98(19) . . . . ?
C3 C4 C9 C8 177.73(16) . . . . ?
C3 C4 C9 C10 -1.6(3) . . . . ?
C3 C12 C13 C14 171.40(17) . . . . ?
C3 C12 C13 N1 -1.4(2) . . . . ?
C4 C3 C12 C11 2.1(3) . . . . ?
C4 C3 C12 C13 -173.08(16) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C4 C9 C10 C11 2.1(3) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C5 C4 C9 C10 -178.84(17) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C7 C8 C9 C10 178.61(19) . . . . ?
C8 C9 C10 C11 -177.17(18) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C3 -1.6(3) . . . . ?
C10 C11 C12 C13 172.46(18) . . . . ?
C11 C12 C13 C14 -3.2(3) . . . . ?
C11 C12 C13 N1 -175.99(17) . . . . ?
C12 C3 C4 C5 176.67(17) . . . . ?
C12 C3 C4 C9 -0.4(2) . . . . ?
C12 C13 C14 C15 52.3(3) . . . . ?
C12 C13 C14 C19 -124.5(2) . . . . ?
C12 C13 N1 C2 -0.4(2) . . . . ?
C12 C13 N1 C20 178.55(15) . . . . ?
C13 C14 C15 C16 -176.15(19) . . . . ?
C13 C14 C19 C18 176.63(18) . . . . ?
C14 C13 N1 C2 -173.60(16) . . . . ?
C14 C13 N1 C20 5.3(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C14 -0.7(3) . . . . ?
C19 C14 C15 C16 0.7(3) . . . . ?
C20 C21 C22 C23 -1.0(3) . . . . ?
C21 C20 C25 C24 0.0(3) . . . . ?
C21 C20 N1 C2 63.0(2) . . . . ?
C21 C20 N1 C13 -115.8(2) . . . . ?
C21 C22 C23 C24 1.4(3) . . . . ?
C21 C22 C23 C26 -178.14(18) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C23 C24 C25 C20 0.5(3) . . . . ?
C25 C20 C21 C22 0.3(3) . . . . ?
C25 C20 N1 C2 -120.34(19) . . . . ?
C25 C20 N1 C13 60.9(2) . . . . ?
C26 C23 C24 C25 178.38(18) . . . . ?
N1 C2 C3 C4 172.09(18) . . . . ?
N1 C2 C3 C12 -2.68(19) . . . . ?
N1 C13 C14 C15 -136.0(2) . . . . ?
N1 C13 C14 C19 47.2(3) . . . . ?
N1 C20 C21 C22 176.94(16) . . . . ?
N1 C20 C25 C24 -176.68(16) . . . . ?
O1 C1 C2 C3 6.2(4) . . . . ?
O1 C1 C2 N1 176.46(19) . . . . ?
C27 C28 C29 C30 -19.1(3) . . . . ?
C27 C28 C29 C38 165.74(19) . . . . ?
C27 C28 N2 C39 -168.88(15) . . . . ?
C27 C28 N2 C46 15.6(2) . . . . ?
C28 C29 C30 C31 0.9(3) . . . . ?
C28 C29 C30 C35 -175.72(18) . . . . ?
C28 C29 C38 C37 177.83(16) . . . . ?
C28 C29 C38 C39 2.82(19) . . . . ?
C29 C28 N2 C39 2.08(19) . . . . ?
C29 C28 N2 C46 -173.47(15) . . . . ?
C29 C30 C31 C32 -177.37(18) . . . . ?
C29 C30 C35 C34 178.02(16) . . . . ?
C29 C30 C35 C36 -0.3(2) . . . . ?
C29 C38 C39 C40 169.69(17) . . . . ?
C29 C38 C39 N2 -1.57(19) . . . . ?
C30 C29 C38 C37 1.8(3) . . . . ?
C30 C29 C38 C39 -173.20(15) . . . . ?
C30 C31 C32 C33 -0.1(3) . . . . ?
C30 C35 C36 C37 1.0(3) . . . . ?
C31 C30 C35 C34 1.2(3) . . . . ?
C31 C30 C35 C36 -177.20(16) . . . . ?
C31 C32 C33 C34 0.6(3) . . . . ?
C32 C33 C34 C35 -0.2(3) . . . . ?
C33 C34 C35 C30 -0.7(3) . . . . ?
C33 C34 C35 C36 177.66(18) . . . . ?
C34 C35 C36 C37 -177.35(17) . . . . ?
C35 C30 C31 C32 -0.8(3) . . . . ?
C35 C36 C37 C38 -0.2(3) . . . . ?
C36 C37 C38 C29 -1.2(3) . . . . ?
C36 C37 C38 C39 172.72(18) . . . . ?
C37 C38 C39 C40 -4.9(3) . . . . ?
C37 C38 C39 N2 -176.12(17) . . . . ?
C38 C29 C30 C31 175.63(17) . . . . ?
C38 C29 C30 C35 -1.0(2) . . . . ?
C38 C39 C40 C41 55.5(3) . . . . ?
C38 C39 C40 C45 -119.2(2) . . . . ?
C38 C39 N2 C28 -0.33(19) . . . . ?
C38 C39 N2 C46 175.33(15) . . . . ?
C39 C40 C41 C42 -174.33(18) . . . . ?
C39 C40 C45 C44 174.32(17) . . . . ?
C40 C39 N2 C28 -171.98(16) . . . . ?
C40 C39 N2 C46 3.7(3) . . . . ?
C40 C41 C42 C43 0.3(3) . . . . ?
C41 C40 C45 C44 -0.3(3) . . . . ?
C41 C42 C43 C44 -1.0(3) . . . . ?
C42 C43 C44 C45 1.1(3) . . . . ?
C43 C44 C45 C40 -0.4(3) . . . . ?
C45 C40 C41 C42 0.4(3) . . . . ?
C46 C47 C48 C49 -0.9(3) . . . . ?
C47 C46 C51 C50 1.1(3) . . . . ?
C47 C46 N2 C28 57.5(2) . . . . ?
C47 C46 N2 C39 -117.5(2) . . . . ?
C47 C48 C49 C50 1.5(3) . . . . ?
C47 C48 C49 C52 -177.66(19) . . . . ?
C48 C49 C50 C51 -0.9(3) . . . . ?
C49 C50 C51 C46 -0.4(3) . . . . ?
C51 C46 C47 C48 -0.5(3) . . . . ?
C51 C46 N2 C28 -125.89(19) . . . . ?
C51 C46 N2 C39 59.1(2) . . . . ?
C52 C49 C50 C51 178.27(18) . . . . ?
N2 C28 C29 C30 172.26(18) . . . . ?
N2 C28 C29 C38 -2.94(18) . . . . ?
N2 C39 C40 C41 -134.64(19) . . . . ?
N2 C39 C40 C45 50.7(2) . . . . ?
N2 C46 C47 C48 176.11(16) . . . . ?
N2 C46 C51 C50 -175.49(15) . . . . ?
O2 C27 C28 C29 10.4(3) . . . . ?
O2 C27 C28 N2 178.15(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc2r9hxh
_database_code_depnum_ccdc_archive 'CCDC 2541377'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.15003255/v1 2026
loop_
_audit_author_name
_audit_author_address
'shiwu lishiwuabcd'
;Shihezi University
China
;
_audit_update_record             
;
2026-03-26 deposited with the CCDC.	2026-06-05 downloaded from the CCDC.
;
_audit_creation_date             2025-03-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 Br N'
_chemical_formula_sum            'C25 H18 Br N'
_chemical_formula_weight         412.31
_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 0.0181 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'

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

_cell_length_a                   11.1703(6)
_cell_length_b                   6.4509(3)
_cell_length_c                   26.2834(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.878(3)
_cell_angle_gamma                90
_cell_volume                     1859.91(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6990
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      72.04
_cell_measurement_theta_min      4.76
_shelx_estimated_absorpt_T_max   0.594
_shelx_estimated_absorpt_T_min   0.527
_exptl_absorpt_coefficient_mu    3.061
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0972 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.8964.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13857
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.998
_diffrn_reflns_theta_min         3.424
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2973
_reflns_number_total             3633
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.054
_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)+(0.0546P)²+1.7096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1173
_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 Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.36079(3) 1.13096(5) 0.43420(2) 0.04073(14) Uani 1 1 d . . . . .
C1 C 0.5979(3) 0.5235(5) 0.26564(11) 0.0342(7) Uani 1 1 d . . . . .
H1A H 0.527734 0.579734 0.278508 0.051 Uiso 1 1 calc R U . . .
H1B H 0.569947 0.418913 0.239011 0.051 Uiso 1 1 calc R U . . .
H1C H 0.639267 0.635768 0.250693 0.051 Uiso 1 1 calc R U . . .
C2 C 0.6849(3) 0.4257(5) 0.30964(10) 0.0267(6) Uani 1 1 d . . . . .
C3 C 0.7637(3) 0.2604(5) 0.31117(10) 0.0253(6) Uani 1 1 d . . . . .
C4 C 0.7932(3) 0.1226(5) 0.27137(11) 0.0283(6) Uani 1 1 d . . . . .
C5 C 0.7483(3) 0.1454(6) 0.21774(12) 0.0371(7) Uani 1 1 d . . . . .
H5 H 0.697860 0.260459 0.205648 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7765(4) 0.0038(7) 0.18275(13) 0.0470(9) Uani 1 1 d . . . . .
H6 H 0.744105 0.020825 0.146889 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8523(4) -0.1651(6) 0.19934(13) 0.0456(9) Uani 1 1 d . . . . .
H7 H 0.870928 -0.262666 0.174896 0.055 Uiso 1 1 calc R U . . .
C8 C 0.8995(3) -0.1893(6) 0.25091(13) 0.0395(7) Uani 1 1 d . . . . .
H8 H 0.951716 -0.303304 0.262100 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8716(3) -0.0470(5) 0.28762(11) 0.0309(6) Uani 1 1 d . . . . .
C10 C 0.9262(3) -0.0734(5) 0.34208(11) 0.0306(6) Uani 1 1 d . . . . .
H10 H 0.980514 -0.185863 0.351957 0.037 Uiso 1 1 calc R U . . .
C11 C 0.9018(3) 0.0568(5) 0.37886(10) 0.0280(6) Uani 1 1 d . . . . .
H11 H 0.940168 0.038080 0.414014 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8176(3) 0.2239(5) 0.36460(10) 0.0248(5) Uani 1 1 d . . . . .
C13 C 0.7723(3) 0.3701(4) 0.39415(10) 0.0245(6) Uani 1 1 d . . . . .
C14 C 0.8045(3) 0.4116(5) 0.45013(10) 0.0254(6) Uani 1 1 d . . . . .
C15 C 0.8076(3) 0.2514(5) 0.48611(11) 0.0290(6) Uani 1 1 d . . . . .
H15 H 0.784024 0.115065 0.474712 0.035 Uiso 1 1 calc R U . . .
C16 C 0.8453(3) 0.2921(6) 0.53877(11) 0.0328(7) Uani 1 1 d . . . . .
H16 H 0.847831 0.182652 0.563127 0.039 Uiso 1 1 calc R U . . .
C17 C 0.8794(3) 0.4910(6) 0.55606(11) 0.0339(7) Uani 1 1 d . . . . .
H17 H 0.906242 0.517576 0.591959 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8737(3) 0.6496(5) 0.52036(12) 0.0323(6) Uani 1 1 d . . . . .
H18 H 0.895326 0.786294 0.532033 0.039 Uiso 1 1 calc R U . . .
C19 C 0.8370(3) 0.6124(5) 0.46778(11) 0.0284(6) Uani 1 1 d . . . . .
H19 H 0.833920 0.723082 0.443730 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6138(3) 0.6452(5) 0.37662(10) 0.0246(6) Uani 1 1 d . . . . .
C21 C 0.5428(3) 0.5899(5) 0.41268(11) 0.0293(6) Uani 1 1 d . . . . .
H21 H 0.545914 0.452109 0.425638 0.035 Uiso 1 1 calc R U . . .
C22 C 0.4678(3) 0.7345(5) 0.42976(11) 0.0323(6) Uani 1 1 d . . . . .
H22 H 0.419781 0.697378 0.454567 0.039 Uiso 1 1 calc R U . . .
C23 C 0.4639(3) 0.9326(5) 0.41030(11) 0.0289(6) Uani 1 1 d . . . . .
C24 C 0.5329(3) 0.9914(5) 0.37378(11) 0.0290(6) Uani 1 1 d . . . . .
H24 H 0.528532 1.128527 0.360400 0.035 Uiso 1 1 calc R U . . .
C25 C 0.6084(3) 0.8444(5) 0.35735(10) 0.0268(6) Uani 1 1 d . . . . .
H25 H 0.656676 0.881583 0.332632 0.032 Uiso 1 1 calc R U . . .
N1 N 0.6922(2) 0.4942(4) 0.36037(8) 0.0248(5) Uani 1 1 d . . . . .


_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 C23 1.905(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.502(4) . ?
C2 C3 1.378(4) . ?
C2 N1 1.392(3) . ?
C3 C4 1.457(4) . ?
C3 C12 1.439(4) . ?
C4 C5 1.412(4) . ?
C4 C9 1.416(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.367(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.408(4) . ?
C9 C10 1.456(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.347(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.433(4) . ?
C12 C13 1.377(4) . ?
C13 C14 1.472(4) . ?
C13 N1 1.390(4) . ?
C14 C15 1.397(4) . ?
C14 C19 1.401(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(4) . ?
C20 C25 1.379(4) . ?
C20 N1 1.428(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.374(5) . ?
C23 C24 1.392(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(4) . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 131.6(3) . . ?
C3 C2 N1 107.2(2) . . ?
N1 C2 C1 121.1(3) . . ?
C2 C3 C4 132.9(3) . . ?
C2 C3 C12 107.6(2) . . ?
C12 C3 C4 119.4(3) . . ?
C5 C4 C3 124.6(3) . . ?
C5 C4 C9 117.7(3) . . ?
C9 C4 C3 117.8(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C10 120.5(3) . . ?
C8 C9 C4 120.1(3) . . ?
C8 C9 C10 119.4(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 121.9(3) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C3 120.8(3) . . ?
C13 C12 C3 107.9(3) . . ?
C13 C12 C11 131.3(3) . . ?
C12 C13 C14 129.9(3) . . ?
C12 C13 N1 107.2(2) . . ?
N1 C13 C14 122.7(3) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 C19 119.2(3) . . ?
C19 C14 C13 119.9(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.1(3) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C21 C20 N1 119.3(3) . . ?
C25 C20 C21 119.9(3) . . ?
C25 C20 N1 120.8(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.0(3) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 Br1 118.7(2) . . ?
C22 C23 C24 121.8(3) . . ?
C24 C23 Br1 119.5(2) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 C23 118.4(3) . . ?
C25 C24 H24 120.8 . . ?
C20 C25 C24 120.6(3) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C2 N1 C20 125.1(2) . . ?
C13 N1 C2 110.0(2) . . ?
C13 N1 C20 124.0(2) . . ?

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 C23 C24 C25 179.3(2) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C1 C2 C3 C12 -175.2(3) . . . . ?
C1 C2 N1 C13 175.7(3) . . . . ?
C1 C2 N1 C20 5.8(4) . . . . ?
C2 C3 C4 C5 5.5(5) . . . . ?
C2 C3 C4 C9 -174.0(3) . . . . ?
C2 C3 C12 C11 178.3(3) . . . . ?
C2 C3 C12 C13 -1.2(3) . . . . ?
C3 C2 N1 C13 -1.6(3) . . . . ?
C3 C2 N1 C20 -171.5(3) . . . . ?
C3 C4 C5 C6 -177.3(3) . . . . ?
C3 C4 C9 C8 177.7(3) . . . . ?
C3 C4 C9 C10 -3.7(4) . . . . ?
C3 C12 C13 C14 -174.8(3) . . . . ?
C3 C12 C13 N1 0.2(3) . . . . ?
C4 C3 C12 C11 1.4(4) . . . . ?
C4 C3 C12 C13 -178.1(3) . . . . ?
C4 C5 C6 C7 -1.1(6) . . . . ?
C4 C9 C10 C11 2.0(5) . . . . ?
C5 C4 C9 C8 -1.8(5) . . . . ?
C5 C4 C9 C10 176.8(3) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C9 0.7(6) . . . . ?
C7 C8 C9 C4 0.4(5) . . . . ?
C7 C8 C9 C10 -178.2(3) . . . . ?
C8 C9 C10 C11 -179.4(3) . . . . ?
C9 C4 C5 C6 2.2(5) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C10 C11 C12 C3 -3.2(4) . . . . ?
C10 C11 C12 C13 176.1(3) . . . . ?
C11 C12 C13 C14 5.8(5) . . . . ?
C11 C12 C13 N1 -179.3(3) . . . . ?
C12 C3 C4 C5 -178.5(3) . . . . ?
C12 C3 C4 C9 2.0(4) . . . . ?
C12 C13 C14 C15 -50.6(4) . . . . ?
C12 C13 C14 C19 127.0(3) . . . . ?
C12 C13 N1 C2 0.9(3) . . . . ?
C12 C13 N1 C20 170.9(3) . . . . ?
C13 C14 C15 C16 176.2(3) . . . . ?
C13 C14 C19 C18 -176.5(3) . . . . ?
C14 C13 N1 C2 176.3(3) . . . . ?
C14 C13 N1 C20 -13.8(4) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C14 C19 C18 1.1(4) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C16 C17 C18 C19 -1.3(5) . . . . ?
C17 C18 C19 C14 0.2(5) . . . . ?
C19 C14 C15 C16 -1.4(4) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C21 C20 C25 C24 0.3(4) . . . . ?
C21 C20 N1 C2 119.6(3) . . . . ?
C21 C20 N1 C13 -48.9(4) . . . . ?
C21 C22 C23 Br1 -179.8(2) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C22 C23 C24 C25 -0.7(4) . . . . ?
C23 C24 C25 C20 0.4(4) . . . . ?
C25 C20 C21 C22 -0.7(4) . . . . ?
C25 C20 N1 C2 -60.9(4) . . . . ?
C25 C20 N1 C13 130.6(3) . . . . ?
N1 C2 C3 C4 178.0(3) . . . . ?
N1 C2 C3 C12 1.7(3) . . . . ?
N1 C13 C14 C15 135.2(3) . . . . ?
N1 C13 C14 C19 -47.2(4) . . . . ?
N1 C20 C21 C22 178.8(3) . . . . ?
N1 C20 C25 C24 -179.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
