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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2457376'
loop_
_audit_author_name
_audit_author_address
'Shaoxiong Yang'
;Yunnan University
China
;
_audit_update_record             
;
2025-06-07 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-03-25
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C26 H19 N O'
_chemical_formula_moiety         'C26 H19 N O'
_chemical_formula_weight         361.42
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8144(9)
_cell_length_b                   8.2022(7)
_cell_length_c                   22.949(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.027(4)
_cell_angle_gamma                90
_cell_volume                     1819.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    5798
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.49
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6525
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1453 before and 0.0859 after correction.
The Ratio of minimum to maximum transmission is 0.8751.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            27788
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4195
_reflns_number_gt                3005
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+1.4675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4195
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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
O1 O 0.82679(14) 0.66688(18) 0.32777(6) 0.0229(3) Uani 1 1 d . . . . .
N1 N 0.69923(16) 0.6447(2) 0.45233(7) 0.0172(4) Uani 1 1 d . . . . .
C1 C 0.6880(2) 0.6987(3) 0.30959(9) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.6387(2) 0.7889(3) 0.25815(9) 0.0248(5) Uani 1 1 d . . . . .
H2 H 0.700058 0.832990 0.234496 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4984(2) 0.8106(3) 0.24350(9) 0.0238(5) Uani 1 1 d . . . . .
H3 H 0.462282 0.869625 0.208603 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4050(2) 0.7473(2) 0.27902(9) 0.0211(4) Uani 1 1 d . . . . .
C5 C 0.2597(2) 0.7677(3) 0.26295(10) 0.0245(5) Uani 1 1 d . . . . .
H5 H 0.222957 0.825608 0.227873 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1718(2) 0.7047(3) 0.29749(10) 0.0244(5) Uani 1 1 d . . . . .
H6 H 0.074629 0.717574 0.285967 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2255(2) 0.6209(3) 0.35014(9) 0.0240(5) Uani 1 1 d . . . . .
H7 H 0.163801 0.578654 0.374008 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3650(2) 0.5993(2) 0.36745(9) 0.0206(4) Uani 1 1 d . . . . .
H8 H 0.399215 0.543553 0.403309 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4585(2) 0.6598(2) 0.33197(9) 0.0181(4) Uani 1 1 d . . . . .
C10 C 0.6037(2) 0.6364(2) 0.34558(8) 0.0177(4) Uani 1 1 d . . . . .
C11 C 0.69103(19) 0.5494(2) 0.39703(8) 0.0165(4) Uani 1 1 d . . . . .
C12 C 0.64683(19) 0.3745(2) 0.40681(9) 0.0180(4) Uani 1 1 d . . . . .
C13 C 0.6591(2) 0.3096(3) 0.46363(9) 0.0226(5) Uani 1 1 d . . . . .
H13 H 0.690000 0.376910 0.497017 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6265(2) 0.1469(3) 0.47181(11) 0.0292(5) Uani 1 1 d . . . . .
H14 H 0.635614 0.103730 0.510713 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5807(2) 0.0476(3) 0.42351(11) 0.0311(6) Uani 1 1 d . . . . .
H15 H 0.560186 -0.063843 0.429203 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5650(2) 0.1117(3) 0.36687(11) 0.0296(5) Uani 1 1 d . . . . .
H16 H 0.531675 0.044760 0.333664 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5980(2) 0.2744(3) 0.35856(10) 0.0224(5) Uani 1 1 d . . . . .
H17 H 0.587145 0.317578 0.319607 0.027 Uiso 1 1 calc R U . . .
C18 C 0.8386(2) 0.5603(2) 0.37940(9) 0.0187(4) Uani 1 1 d . . . . .
H18 H 0.873796 0.449949 0.370876 0.022 Uiso 1 1 calc R U . . .
C19 C 0.9293(2) 0.6384(2) 0.43273(9) 0.0188(4) Uani 1 1 d . . . . .
H19A H 0.996953 0.559404 0.453610 0.023 Uiso 1 1 calc R U . . .
H19B H 0.979534 0.734135 0.420868 0.023 Uiso 1 1 calc R U . . .
C20 C 0.82485(19) 0.6888(2) 0.47093(8) 0.0170(4) Uani 1 1 d . . . . .
C21 C 0.8657(2) 0.7798(2) 0.52685(8) 0.0175(4) Uani 1 1 d . . . . .
C22 C 1.0019(2) 0.8330(2) 0.54386(9) 0.0218(4) Uani 1 1 d . . . . .
H22 H 1.068074 0.810775 0.519242 0.026 Uiso 1 1 calc R U . . .
C23 C 1.0416(2) 0.9181(3) 0.59643(9) 0.0246(5) Uani 1 1 d . . . . .
H23 H 1.134686 0.953358 0.607780 0.029 Uiso 1 1 calc R U . . .
C24 C 0.9452(2) 0.9514(3) 0.63218(9) 0.0247(5) Uani 1 1 d . . . . .
H24 H 0.972015 1.009973 0.668062 0.030 Uiso 1 1 calc R U . . .
C25 C 0.8087(2) 0.8993(3) 0.61572(9) 0.0255(5) Uani 1 1 d . . . . .
H25 H 0.742618 0.923246 0.640238 0.031 Uiso 1 1 calc R U . . .
C26 C 0.7693(2) 0.8129(3) 0.56381(9) 0.0213(4) Uani 1 1 d . . . . .
H26 H 0.676593 0.775775 0.553138 0.026 Uiso 1 1 calc R U . . .


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
O1 C1 1.378(2) . ?
O1 C18 1.461(2) . ?
N1 C11 1.480(2) . ?
N1 C20 1.284(2) . ?
C1 C2 1.406(3) . ?
C1 C10 1.366(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.426(3) . ?
C4 C5 1.420(3) . ?
C4 C9 1.430(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.370(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.410(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.369(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.419(3) . ?
C9 C10 1.417(3) . ?
C10 C11 1.512(3) . ?
C11 C12 1.527(3) . ?
C11 C18 1.572(3) . ?
C12 C13 1.394(3) . ?
C12 C17 1.394(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(3) . ?
C17 H17 0.9500 . ?
C18 H18 1.0000 . ?
C18 C19 1.524(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.517(3) . ?
C20 C21 1.479(3) . ?
C21 C22 1.396(3) . ?
C21 C26 1.403(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.394(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(3) . ?
C26 H26 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
C1 O1 C18 107.07(14) . . ?
C20 N1 C11 109.82(16) . . ?
O1 C1 C2 122.13(18) . . ?
C10 C1 O1 114.64(18) . . ?
C10 C1 C2 123.23(19) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.32(19) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.03(19) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C9 119.39(19) . . ?
C5 C4 C3 121.69(19) . . ?
C5 C4 C9 118.91(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.15(19) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 118.99(18) . . ?
C10 C9 C4 117.49(18) . . ?
C10 C9 C8 123.51(18) . . ?
C1 C10 C9 120.50(18) . . ?
C1 C10 C11 109.13(17) . . ?
C9 C10 C11 130.36(18) . . ?
N1 C11 C10 111.05(16) . . ?
N1 C11 C12 110.14(16) . . ?
N1 C11 C18 106.01(15) . . ?
C10 C11 C12 114.92(16) . . ?
C10 C11 C18 101.23(15) . . ?
C12 C11 C18 112.88(16) . . ?
C13 C12 C11 121.03(18) . . ?
C13 C12 C17 118.70(19) . . ?
C17 C12 C11 120.23(18) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
O1 C18 C11 107.22(15) . . ?
O1 C18 H18 111.4 . . ?
O1 C18 C19 110.63(16) . . ?
C11 C18 H18 111.4 . . ?
C19 C18 C11 104.63(15) . . ?
C19 C18 H18 111.4 . . ?
C18 C19 H19A 111.2 . . ?
C18 C19 H19B 111.2 . . ?
H19A C19 H19B 109.1 . . ?
C20 C19 C18 102.68(15) . . ?
C20 C19 H19A 111.2 . . ?
C20 C19 H19B 111.2 . . ?
N1 C20 C19 115.93(17) . . ?
N1 C20 C21 122.00(18) . . ?
C21 C20 C19 122.06(17) . . ?
C22 C21 C20 120.14(18) . . ?
C22 C21 C26 118.98(18) . . ?
C26 C21 C20 120.88(18) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.68(19) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.9 . . ?
C25 C26 C21 120.22(19) . . ?
C25 C26 H26 119.9 . . ?

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
O1 C1 C2 C3 178.71(19) . . . . ?
O1 C1 C10 C9 -179.83(17) . . . . ?
O1 C1 C10 C11 0.7(2) . . . . ?
O1 C18 C19 C20 106.70(17) . . . . ?
N1 C11 C12 C13 -18.9(2) . . . . ?
N1 C11 C12 C17 163.50(17) . . . . ?
N1 C11 C18 O1 -107.93(17) . . . . ?
N1 C11 C18 C19 9.59(19) . . . . ?
N1 C20 C21 C22 -176.56(19) . . . . ?
N1 C20 C21 C26 4.0(3) . . . . ?
C1 O1 C18 C11 -8.0(2) . . . . ?
C1 O1 C18 C19 -121.56(17) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C10 C11 N1 106.80(19) . . . . ?
C1 C10 C11 C12 -127.36(18) . . . . ?
C1 C10 C11 C18 -5.4(2) . . . . ?
C2 C1 C10 C9 0.4(3) . . . . ?
C2 C1 C10 C11 -179.05(19) . . . . ?
C2 C3 C4 C5 -178.8(2) . . . . ?
C2 C3 C4 C9 0.7(3) . . . . ?
C3 C4 C5 C6 179.5(2) . . . . ?
C3 C4 C9 C8 179.15(19) . . . . ?
C3 C4 C9 C10 -1.8(3) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C4 C9 C10 C1 1.3(3) . . . . ?
C4 C9 C10 C11 -179.40(19) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
C5 C4 C9 C10 177.69(18) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C7 C8 C9 C4 1.7(3) . . . . ?
C7 C8 C9 C10 -177.26(19) . . . . ?
C8 C9 C10 C1 -179.71(19) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C9 C10 C11 N1 -72.6(3) . . . . ?
C9 C10 C11 C12 53.3(3) . . . . ?
C9 C10 C11 C18 175.2(2) . . . . ?
C10 C1 C2 C3 -1.6(3) . . . . ?
C10 C11 C12 C13 -145.24(18) . . . . ?
C10 C11 C12 C17 37.2(2) . . . . ?
C10 C11 C18 O1 8.05(19) . . . . ?
C10 C11 C18 C19 125.57(16) . . . . ?
C11 N1 C20 C19 1.4(2) . . . . ?
C11 N1 C20 C21 -177.34(17) . . . . ?
C11 C12 C13 C14 -176.03(18) . . . . ?
C11 C12 C17 C16 176.25(18) . . . . ?
C11 C18 C19 C20 -8.46(19) . . . . ?
C12 C11 C18 O1 131.42(17) . . . . ?
C12 C11 C18 C19 -111.06(18) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C12 C17 C16 -1.4(3) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C17 C12 C13 C14 1.6(3) . . . . ?
C18 O1 C1 C2 -175.42(19) . . . . ?
C18 O1 C1 C10 4.8(2) . . . . ?
C18 C11 C12 C13 99.3(2) . . . . ?
C18 C11 C12 C17 -78.2(2) . . . . ?
C18 C19 C20 N1 4.9(2) . . . . ?
C18 C19 C20 C21 -176.35(17) . . . . ?
C19 C20 C21 C22 4.8(3) . . . . ?
C19 C20 C21 C26 -174.58(18) . . . . ?
C20 N1 C11 C10 -116.08(18) . . . . ?
C20 N1 C11 C12 115.46(18) . . . . ?
C20 N1 C11 C18 -7.0(2) . . . . ?
C20 C21 C22 C23 -179.73(19) . . . . ?
C20 C21 C26 C25 -179.48(19) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C21 C26 C25 1.1(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C24 C25 C26 C21 -1.2(3) . . . . ?
C26 C21 C22 C23 -0.3(3) . . . . ?

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2457377'
loop_
_audit_author_name
_audit_author_address
'Shaoxiong Yang'
;Yunnan University
China
;
_audit_update_record             
;
2025-06-07 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-05-19
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2018/3
_diffrn_source_power             0.07
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C27 H26 N2 O2'
_chemical_formula_moiety         'C27 H26 N2 O2'
_chemical_formula_weight         410.50
_chemical_melting_point          ?
_exptl_crystal_colour_primary    colourless
_space_group_crystal_system      monoclinic
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_IT_number           15
_space_group_name_H-M_alt        C2/c
_space_group_name_Hall           '-C 2yc'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.3054(7)
_cell_length_b                   9.0717(3)
_cell_length_c                   21.5229(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.9950(10)
_cell_angle_gamma                90
_cell_volume                     4219.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.31
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6304
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1181 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8454.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.985
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            31646
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_theta_min         2.041
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5254
_reflns_number_gt                4338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+4.8237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5254
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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
O1 O 0.70030(5) 0.48038(12) 0.49116(5) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.61515(4) 0.38732(10) 0.40813(4) 0.0156(2) Uani 1 1 d . . . . .
N1 N 0.60856(5) 0.49995(12) 0.27480(5) 0.0154(2) Uani 1 1 d . . . . .
N2 N 0.69281(5) 0.47587(12) 0.38235(5) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.50510(6) 0.64050(15) 0.17021(7) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.494117 0.562083 0.192855 0.022 Uiso 1 1 calc R U . . .
C2 C 0.45949(7) 0.73190(16) 0.12778(7) 0.0218(3) Uani 1 1 d . . . . .
H2 H 0.417340 0.715114 0.121040 0.026 Uiso 1 1 calc R U . . .
C3 C 0.47525(7) 0.84798(16) 0.09509(7) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.443950 0.911146 0.066535 0.028 Uiso 1 1 calc R U . . .
C4 C 0.53668(7) 0.87158(15) 0.10416(7) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.547485 0.951031 0.081911 0.027 Uiso 1 1 calc R U . . .
C5 C 0.58243(7) 0.77881(15) 0.14586(7) 0.0195(3) Uani 1 1 d . . . . .
H5 H 0.624385 0.793993 0.151353 0.023 Uiso 1 1 calc R U . . .
C6 C 0.56702(6) 0.66331(14) 0.17975(6) 0.0161(3) Uani 1 1 d . . . . .
C7 C 0.61594(6) 0.56762(14) 0.22605(6) 0.0156(3) Uani 1 1 d . . . . .
C8 C 0.67698(6) 0.54233(16) 0.21795(7) 0.0183(3) Uani 1 1 d . . . . .
H8A H 0.697579 0.636845 0.216258 0.022 Uiso 1 1 calc R U . . .
H8B H 0.671197 0.484961 0.176911 0.022 Uiso 1 1 calc R U . . .
C9 C 0.71410(6) 0.45445(14) 0.28132(6) 0.0158(3) Uani 1 1 d . . . . .
H9 H 0.732428 0.363303 0.270203 0.019 Uiso 1 1 calc R U . . .
C10 C 0.76201(6) 0.54361(14) 0.33458(7) 0.0158(3) Uani 1 1 d . . . . .
C11 C 0.81420(6) 0.61152(16) 0.33166(7) 0.0197(3) Uani 1 1 d . . . . .
H11 H 0.824364 0.601941 0.293026 0.024 Uiso 1 1 calc R U . . .
C12 C 0.85155(6) 0.69430(16) 0.38662(7) 0.0228(3) Uani 1 1 d . . . . .
H12 H 0.887442 0.741988 0.385500 0.027 Uiso 1 1 calc R U . . .
C13 C 0.83633(6) 0.70708(15) 0.44292(7) 0.0213(3) Uani 1 1 d . . . . .
H13 H 0.861824 0.765043 0.479650 0.026 Uiso 1 1 calc R U . . .
C14 C 0.78460(6) 0.63697(14) 0.44685(7) 0.0178(3) Uani 1 1 d . . . . .
H14 H 0.774823 0.645018 0.485787 0.021 Uiso 1 1 calc R U . . .
C15 C 0.74775(6) 0.55473(14) 0.39175(6) 0.0147(3) Uani 1 1 d . . . . .
C16 C 0.66493(6) 0.41608(14) 0.31299(6) 0.0140(3) Uani 1 1 d . . . . .
C17 C 0.65330(6) 0.25090(14) 0.31334(6) 0.0142(2) Uani 1 1 d . . . . .
C18 C 0.59745(6) 0.18768(15) 0.27302(7) 0.0174(3) Uani 1 1 d . . . . .
H18 H 0.564130 0.248534 0.246434 0.021 Uiso 1 1 calc R U . . .
C19 C 0.59027(7) 0.03472(16) 0.27155(7) 0.0221(3) Uani 1 1 d . . . . .
H19 H 0.552035 -0.008251 0.243919 0.027 Uiso 1 1 calc R U . . .
C20 C 0.63877(7) -0.05471(16) 0.31030(7) 0.0239(3) Uani 1 1 d . . . . .
H20 H 0.633817 -0.158760 0.308777 0.029 Uiso 1 1 calc R U . . .
C21 C 0.69445(7) 0.00751(16) 0.35123(7) 0.0226(3) Uani 1 1 d . . . . .
H21 H 0.727529 -0.053466 0.378227 0.027 Uiso 1 1 calc R U . . .
C22 C 0.70154(7) 0.16013(15) 0.35247(7) 0.0188(3) Uani 1 1 d . . . . .
H22 H 0.739732 0.202840 0.380349 0.023 Uiso 1 1 calc R U . . .
C23 C 0.67141(6) 0.44923(14) 0.43292(6) 0.0157(3) Uani 1 1 d . . . . .
C24 C 0.59015(6) 0.31627(15) 0.45473(6) 0.0166(3) Uani 1 1 d . . . . .
C25 C 0.52825(6) 0.25732(16) 0.40688(7) 0.0217(3) Uani 1 1 d . . . . .
H25A H 0.502282 0.339598 0.382529 0.033 Uiso 1 1 calc R U . . .
H25B H 0.507478 0.204925 0.432379 0.033 Uiso 1 1 calc R U . . .
H25C H 0.535110 0.189470 0.374908 0.033 Uiso 1 1 calc R U . . .
C26 C 0.63308(7) 0.19100(15) 0.49075(7) 0.0212(3) Uani 1 1 d . . . . .
H26A H 0.639024 0.124727 0.457702 0.032 Uiso 1 1 calc R U . . .
H26B H 0.614735 0.136093 0.517931 0.032 Uiso 1 1 calc R U . . .
H26C H 0.673142 0.231444 0.519830 0.032 Uiso 1 1 calc R U . . .
C27 C 0.58028(7) 0.42866(16) 0.50232(7) 0.0221(3) Uani 1 1 d . . . . .
H27A H 0.620464 0.459542 0.535224 0.033 Uiso 1 1 calc R U . . .
H27B H 0.555601 0.384146 0.525587 0.033 Uiso 1 1 calc R U . . .
H27C H 0.558413 0.514629 0.476768 0.033 Uiso 1 1 calc R U . . .


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
O1 C23 1.2134(16) . ?
O2 C23 1.3399(16) . ?
O2 C24 1.4828(15) . ?
N1 C7 1.2817(17) . ?
N1 C16 1.4735(16) . ?
N2 C15 1.4134(17) . ?
N2 C16 1.4894(16) . ?
N2 C23 1.3778(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.3871(19) . ?
C1 C6 1.3948(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3983(19) . ?
C6 C7 1.4817(18) . ?
C7 C8 1.5140(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5362(18) . ?
C9 H9 1.0000 . ?
C9 C10 1.5021(18) . ?
C9 C16 1.5761(18) . ?
C10 C11 1.3857(19) . ?
C10 C15 1.3932(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.396(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.3921(18) . ?
C16 C17 1.5233(17) . ?
C17 C18 1.3892(18) . ?
C17 C22 1.3935(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3966(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.3934(19) . ?
C22 H22 0.9500 . ?
C24 C25 1.5215(19) . ?
C24 C26 1.5206(19) . ?
C24 C27 1.5224(19) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C23 O2 C24 119.12(10) . . ?
C7 N1 C16 109.82(11) . . ?
C15 N2 C16 111.07(10) . . ?
C23 N2 C15 123.52(11) . . ?
C23 N2 C16 125.22(11) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.24(13) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.23(14) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.01(13) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.92(13) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.37(13) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.22(12) . . ?
C1 C6 C7 120.34(12) . . ?
C5 C6 C7 120.43(12) . . ?
N1 C7 C6 121.72(12) . . ?
N1 C7 C8 116.20(12) . . ?
C6 C7 C8 122.07(11) . . ?
C7 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
C7 C8 C9 102.56(10) . . ?
H8A C8 H8B 109.2 . . ?
C9 C8 H8A 111.3 . . ?
C9 C8 H8B 111.3 . . ?
C8 C9 H9 111.5 . . ?
C8 C9 C16 103.87(10) . . ?
C10 C9 C8 114.11(11) . . ?
C10 C9 H9 111.5 . . ?
C10 C9 C16 104.00(10) . . ?
C16 C9 H9 111.5 . . ?
C11 C10 C9 128.24(12) . . ?
C11 C10 C15 120.77(13) . . ?
C15 C10 C9 110.98(11) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.68(13) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.14(13) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.62(13) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.69(13) . . ?
C15 C14 H14 121.2 . . ?
C10 C15 N2 109.87(11) . . ?
C14 C15 N2 129.04(12) . . ?
C14 C15 C10 121.07(12) . . ?
N1 C16 N2 109.52(10) . . ?
N1 C16 C9 106.58(10) . . ?
N1 C16 C17 112.80(10) . . ?
N2 C16 C9 103.77(10) . . ?
N2 C16 C17 111.41(10) . . ?
C17 C16 C9 112.26(10) . . ?
C18 C17 C16 121.99(12) . . ?
C18 C17 C22 119.25(12) . . ?
C22 C17 C16 118.65(11) . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.05(13) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.23(13) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.12(13) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.52(13) . . ?
C22 C21 H21 120.2 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.83(13) . . ?
C21 C22 H22 119.6 . . ?
O1 C23 O2 126.19(12) . . ?
O1 C23 N2 123.39(12) . . ?
O2 C23 N2 110.42(11) . . ?
O2 C24 C25 102.01(10) . . ?
O2 C24 C26 108.64(10) . . ?
O2 C24 C27 111.14(10) . . ?
C25 C24 C27 110.30(12) . . ?
C26 C24 C25 111.00(11) . . ?
C26 C24 C27 113.20(11) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
N1 C7 C8 C9 -7.74(15) . . . . ?
N1 C16 C17 C18 9.30(17) . . . . ?
N1 C16 C17 C22 -174.49(11) . . . . ?
N2 C16 C17 C18 132.95(12) . . . . ?
N2 C16 C17 C22 -50.83(15) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C6 C7 N1 -25.09(19) . . . . ?
C1 C6 C7 C8 153.99(12) . . . . ?
C2 C1 C6 C5 -0.26(19) . . . . ?
C2 C1 C6 C7 178.82(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 C5 C6 C1 1.24(19) . . . . ?
C4 C5 C6 C7 -177.84(12) . . . . ?
C5 C6 C7 N1 153.98(13) . . . . ?
C5 C6 C7 C8 -26.94(18) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C6 C7 C8 C9 173.13(11) . . . . ?
C7 N1 C16 N2 116.16(12) . . . . ?
C7 N1 C16 C9 4.50(14) . . . . ?
C7 N1 C16 C17 -119.15(12) . . . . ?
C7 C8 C9 C10 -103.22(12) . . . . ?
C7 C8 C9 C16 9.33(13) . . . . ?
C8 C9 C10 C11 -64.21(18) . . . . ?
C8 C9 C10 C15 114.91(13) . . . . ?
C8 C9 C16 N1 -8.82(13) . . . . ?
C8 C9 C16 N2 -124.42(11) . . . . ?
C8 C9 C16 C17 115.16(12) . . . . ?
C9 C10 C11 C12 177.59(13) . . . . ?
C9 C10 C15 N2 1.06(15) . . . . ?
C9 C10 C15 C14 -177.69(11) . . . . ?
C9 C16 C17 C18 -111.15(13) . . . . ?
C9 C16 C17 C22 65.07(15) . . . . ?
C10 C9 C16 N1 110.86(11) . . . . ?
C10 C9 C16 N2 -4.73(12) . . . . ?
C10 C9 C16 C17 -125.16(11) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C11 C10 C15 N2 -179.74(12) . . . . ?
C11 C10 C15 C14 1.5(2) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 N2 -178.78(13) . . . . ?
C13 C14 C15 C10 -0.30(19) . . . . ?
C15 N2 C16 N1 -107.80(12) . . . . ?
C15 N2 C16 C9 5.70(13) . . . . ?
C15 N2 C16 C17 126.70(11) . . . . ?
C15 N2 C23 O1 -6.3(2) . . . . ?
C15 N2 C23 O2 172.92(11) . . . . ?
C15 C10 C11 C12 -1.5(2) . . . . ?
C16 N1 C7 C6 -178.80(11) . . . . ?
C16 N1 C7 C8 2.07(15) . . . . ?
C16 N2 C15 C10 -4.45(14) . . . . ?
C16 N2 C15 C14 174.17(13) . . . . ?
C16 N2 C23 O1 168.28(12) . . . . ?
C16 N2 C23 O2 -12.53(17) . . . . ?
C16 C9 C10 C11 -176.69(13) . . . . ?
C16 C9 C10 C15 2.44(14) . . . . ?
C16 C17 C18 C19 175.63(12) . . . . ?
C16 C17 C22 C21 -175.91(12) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C17 C22 C21 0.41(19) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C19 C20 C21 C22 -0.8(2) . . . . ?
C20 C21 C22 C17 0.3(2) . . . . ?
C22 C17 C18 C19 -0.56(19) . . . . ?
C23 O2 C24 C25 -178.06(11) . . . . ?
C23 O2 C24 C26 -60.77(14) . . . . ?
C23 O2 C24 C27 64.40(15) . . . . ?
C23 N2 C15 C10 170.78(12) . . . . ?
C23 N2 C15 C14 -10.6(2) . . . . ?
C23 N2 C16 N1 77.06(15) . . . . ?
C23 N2 C16 C9 -169.44(12) . . . . ?
C23 N2 C16 C17 -48.44(16) . . . . ?
C24 O2 C23 O1 -15.78(19) . . . . ?
C24 O2 C23 N2 165.06(10) . . . . ?

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2457378'
loop_
_audit_author_name
_audit_author_address
'Shaoxiong Yang'
;Yunnan University
China
;
_audit_update_record             
;
2025-06-07 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-05-07
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2018/3
_diffrn_source_power             0.07
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C22 H23 Br N2 O2'
_chemical_formula_moiety         'C22 H23 Br N2 O2'
_chemical_formula_weight         427.33
_chemical_melting_point          ?
_exptl_crystal_colour_primary    colourless
_space_group_crystal_system      monoclinic
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;

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                   10.7771(5)
_cell_length_b                   15.1534(6)
_cell_length_c                   12.5418(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.628(2)
_cell_angle_gamma                90
_cell_volume                     1972.48(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.29
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5795
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1090 before and 0.0659 after correction.
The Ratio of minimum to maximum transmission is 0.7771.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.590
_shelx_estimated_absorpt_T_max   0.902
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            28385
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_theta_min         1.962
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4926
_reflns_number_gt                4259
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0116P)²+1.8755P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4926
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.06623(2) 0.48733(2) 0.33260(2) 0.01789(6) Uani 1 1 d . . . . .
O1 O 0.64697(12) 0.68559(9) 0.63099(11) 0.0209(3) Uani 1 1 d . . . . .
O2 O 0.62241(11) 0.77647(8) 0.76924(10) 0.0167(2) Uani 1 1 d . . . . .
N1 N 0.20860(14) 0.64023(9) 0.77596(12) 0.0151(3) Uani 1 1 d . . . . .
N2 N 0.45576(13) 0.69781(9) 0.67515(12) 0.0143(3) Uani 1 1 d . . . . .
C1 C 0.18727(17) 0.53921(11) 0.96310(14) 0.0167(3) Uani 1 1 d . . . . .
H1 H 0.112280 0.544330 0.902752 0.020 Uiso 1 1 calc R U . . .
C2 C 0.18549(18) 0.48572(12) 1.05221(15) 0.0192(3) Uani 1 1 d . . . . .
H2 H 0.109371 0.454295 1.052679 0.023 Uiso 1 1 calc R U . . .
C3 C 0.29493(19) 0.47783(11) 1.14116(15) 0.0199(4) Uani 1 1 d . . . . .
H3 H 0.293828 0.440533 1.201784 0.024 Uiso 1 1 calc R U . . .
C4 C 0.40537(18) 0.52454(12) 1.14094(15) 0.0209(4) Uani 1 1 d . . . . .
H4 H 0.479803 0.519713 1.201862 0.025 Uiso 1 1 calc R U . . .
C5 C 0.40754(18) 0.57857(12) 1.05162(15) 0.0184(3) Uani 1 1 d . . . . .
H5 H 0.483415 0.610674 1.052133 0.022 Uiso 1 1 calc R U . . .
C6 C 0.29907(17) 0.58586(11) 0.96141(14) 0.0141(3) Uani 1 1 d . . . . .
C7 C 0.30233(16) 0.64030(10) 0.86428(13) 0.0133(3) Uani 1 1 d . . . . .
C8 C 0.41554(17) 0.69832(11) 0.86311(14) 0.0161(3) Uani 1 1 d . . . . .
H8A H 0.496196 0.663617 0.877551 0.019 Uiso 1 1 calc R U . . .
H8B H 0.426423 0.746038 0.918788 0.019 Uiso 1 1 calc R U . . .
C9 C 0.37833(16) 0.73564(11) 0.74527(14) 0.0138(3) Uani 1 1 d . . . . .
H9 H 0.381446 0.801595 0.745591 0.017 Uiso 1 1 calc R U . . .
C10 C 0.23832(16) 0.70090(11) 0.69320(13) 0.0136(3) Uani 1 1 d . . . . .
C11 C 0.13591(18) 0.77310(12) 0.66475(16) 0.0208(4) Uani 1 1 d . . . . .
H11A H 0.050876 0.746165 0.635360 0.031 Uiso 1 1 calc R U . . .
H11B H 0.154172 0.812624 0.609000 0.031 Uiso 1 1 calc R U . . .
H11C H 0.136955 0.806871 0.731626 0.031 Uiso 1 1 calc R U . . .
C12 C 0.25069(16) 0.64830(10) 0.59385(13) 0.0125(3) Uani 1 1 d . . . . .
C13 C 0.15594(16) 0.60335(11) 0.51620(14) 0.0145(3) Uani 1 1 d . . . . .
H13 H 0.068538 0.605166 0.518358 0.017 Uiso 1 1 calc R U . . .
C14 C 0.19247(16) 0.55550(11) 0.43505(14) 0.0145(3) Uani 1 1 d . . . . .
C15 C 0.31965(17) 0.55258(11) 0.43020(14) 0.0159(3) Uani 1 1 d . . . . .
H15 H 0.341699 0.519272 0.373784 0.019 Uiso 1 1 calc R U . . .
C16 C 0.41498(17) 0.59820(11) 0.50759(14) 0.0152(3) Uani 1 1 d . . . . .
H16 H 0.502236 0.596757 0.504966 0.018 Uiso 1 1 calc R U . . .
C17 C 0.37833(16) 0.64609(10) 0.58907(13) 0.0127(3) Uani 1 1 d . . . . .
C18 C 0.58267(17) 0.71767(11) 0.68679(14) 0.0151(3) Uani 1 1 d . . . . .
C19 C 0.75471(16) 0.81387(11) 0.79461(14) 0.0162(3) Uani 1 1 d . . . . .
C20 C 0.75293(18) 0.87935(12) 0.88564(16) 0.0219(4) Uani 1 1 d . . . . .
H20A H 0.684671 0.922913 0.857836 0.033 Uiso 1 1 calc R U . . .
H20B H 0.836365 0.909444 0.909045 0.033 Uiso 1 1 calc R U . . .
H20C H 0.736620 0.847999 0.948860 0.033 Uiso 1 1 calc R U . . .
C21 C 0.85373(18) 0.74162(12) 0.83705(17) 0.0243(4) Uani 1 1 d . . . . .
H21A H 0.834296 0.711633 0.899892 0.036 Uiso 1 1 calc R U . . .
H21B H 0.939945 0.767801 0.860845 0.036 Uiso 1 1 calc R U . . .
H21C H 0.850728 0.698886 0.777760 0.036 Uiso 1 1 calc R U . . .
C22 C 0.77446(19) 0.86018(13) 0.69310(16) 0.0249(4) Uani 1 1 d . . . . .
H22A H 0.770333 0.816827 0.634269 0.037 Uiso 1 1 calc R U . . .
H22B H 0.858943 0.889063 0.712118 0.037 Uiso 1 1 calc R U . . .
H22C H 0.706851 0.904555 0.667393 0.037 Uiso 1 1 calc R U . . .


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 C14 1.9045(16) . ?
O1 C18 1.212(2) . ?
O2 C18 1.345(2) . ?
O2 C19 1.4869(19) . ?
N1 C7 1.282(2) . ?
N1 C10 1.485(2) . ?
N2 C9 1.481(2) . ?
N2 C17 1.411(2) . ?
N2 C18 1.369(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(2) . ?
C1 C6 1.402(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(2) . ?
C6 C7 1.479(2) . ?
C7 C8 1.507(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.531(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.565(2) . ?
C10 C11 1.527(2) . ?
C10 C12 1.515(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.385(2) . ?
C12 C17 1.393(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(2) . ?
C14 C15 1.389(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(2) . ?
C19 C20 1.517(2) . ?
C19 C21 1.521(2) . ?
C19 C22 1.518(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C18 O2 C19 120.37(13) . . ?
C7 N1 C10 109.59(14) . . ?
C17 N2 C9 110.95(13) . . ?
C18 N2 C9 123.92(14) . . ?
C18 N2 C17 124.85(14) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.40(16) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.25(17) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.79(16) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.17(17) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.46(17) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 120.31(15) . . ?
C5 C6 C1 118.92(16) . . ?
C5 C6 C7 120.75(15) . . ?
N1 C7 C6 121.52(15) . . ?
N1 C7 C8 116.32(15) . . ?
C6 C7 C8 122.15(15) . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C7 C8 C9 102.86(13) . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
N2 C9 C8 112.78(14) . . ?
N2 C9 H9 111.4 . . ?
N2 C9 C10 104.84(13) . . ?
C8 C9 H9 111.4 . . ?
C8 C9 C10 104.53(13) . . ?
C10 C9 H9 111.4 . . ?
N1 C10 C9 106.37(13) . . ?
N1 C10 C11 109.19(13) . . ?
N1 C10 C12 109.42(13) . . ?
C11 C10 C9 114.30(14) . . ?
C12 C10 C9 103.39(13) . . ?
C12 C10 C11 113.77(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 128.70(15) . . ?
C13 C12 C17 120.48(15) . . ?
C17 C12 C10 110.77(14) . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.07(15) . . ?
C14 C13 H13 121.0 . . ?
C13 C14 Br1 119.02(13) . . ?
C15 C14 Br1 119.16(13) . . ?
C15 C14 C13 121.74(15) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.35(16) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 121.1 . . ?
C15 C16 C17 117.89(16) . . ?
C17 C16 H16 121.1 . . ?
C12 C17 N2 109.94(14) . . ?
C12 C17 C16 121.46(15) . . ?
C16 C17 N2 128.60(15) . . ?
O1 C18 O2 126.65(16) . . ?
O1 C18 N2 124.10(16) . . ?
O2 C18 N2 109.25(14) . . ?
O2 C19 C20 101.81(13) . . ?
O2 C19 C21 110.02(14) . . ?
O2 C19 C22 109.86(14) . . ?
C20 C19 C21 110.93(15) . . ?
C20 C19 C22 111.22(15) . . ?
C22 C19 C21 112.49(16) . . ?
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 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C14 C15 C16 -176.73(13) . . . . ?
N1 C7 C8 C9 -3.14(19) . . . . ?
N1 C10 C12 C13 67.8(2) . . . . ?
N1 C10 C12 C17 -109.80(15) . . . . ?
N2 C9 C10 N1 113.21(14) . . . . ?
N2 C9 C10 C11 -126.23(15) . . . . ?
N2 C9 C10 C12 -2.02(16) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C6 C7 N1 -6.3(2) . . . . ?
C1 C6 C7 C8 174.04(15) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C1 C6 C7 177.68(15) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 -177.54(16) . . . . ?
C5 C6 C7 N1 172.37(16) . . . . ?
C5 C6 C7 C8 -7.3(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C7 C8 C9 176.53(14) . . . . ?
C7 N1 C10 C9 3.97(17) . . . . ?
C7 N1 C10 C11 -119.84(16) . . . . ?
C7 N1 C10 C12 115.04(15) . . . . ?
C7 C8 C9 N2 -108.21(15) . . . . ?
C7 C8 C9 C10 5.10(16) . . . . ?
C8 C9 C10 N1 -5.64(16) . . . . ?
C8 C9 C10 C11 114.93(15) . . . . ?
C8 C9 C10 C12 -120.87(13) . . . . ?
C9 N2 C17 C12 1.81(18) . . . . ?
C9 N2 C17 C16 -178.52(16) . . . . ?
C9 N2 C18 O1 178.53(16) . . . . ?
C9 N2 C18 O2 -0.8(2) . . . . ?
C9 C10 C12 C13 -179.16(16) . . . . ?
C9 C10 C12 C17 3.23(17) . . . . ?
C10 N1 C7 C6 179.78(14) . . . . ?
C10 N1 C7 C8 -0.5(2) . . . . ?
C10 C12 C13 C14 -176.58(15) . . . . ?
C10 C12 C17 N2 -3.23(18) . . . . ?
C10 C12 C17 C16 177.07(15) . . . . ?
C11 C10 C12 C13 -54.6(2) . . . . ?
C11 C10 C12 C17 127.77(15) . . . . ?
C12 C13 C14 Br1 176.27(12) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C12 C17 N2 178.94(14) . . . . ?
C13 C12 C17 C16 -0.8(2) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 N2 -179.36(16) . . . . ?
C15 C16 C17 C12 0.3(2) . . . . ?
C17 N2 C9 C8 113.40(15) . . . . ?
C17 N2 C9 C10 0.28(17) . . . . ?
C17 N2 C18 O1 -8.0(3) . . . . ?
C17 N2 C18 O2 172.63(14) . . . . ?
C17 C12 C13 C14 0.8(2) . . . . ?
C18 O2 C19 C20 176.55(14) . . . . ?
C18 O2 C19 C21 -65.76(19) . . . . ?
C18 O2 C19 C22 58.6(2) . . . . ?
C18 N2 C9 C8 -72.3(2) . . . . ?
C18 N2 C9 C10 174.54(15) . . . . ?
C18 N2 C17 C12 -172.39(15) . . . . ?
C18 N2 C17 C16 7.3(3) . . . . ?
C19 O2 C18 O1 4.6(3) . . . . ?
C19 O2 C18 N2 -176.01(13) . . . . ?

####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2457379'
loop_
_audit_author_name
_audit_author_address
'Shaoxiong Yang'
;Yunnan University
China
;
_audit_update_record             
;
2025-06-07 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-04-09
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C20 H19 N O'
_chemical_formula_moiety         'C20 H19 N O'
_chemical_formula_weight         289.36
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C28(H28A,H28B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18),
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C36(H36), C37(H37),
  C38(H38), C39(H39)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;

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                   18.0371(7)
_cell_length_b                   10.3994(4)
_cell_length_c                   17.8291(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.2320(10)
_cell_angle_gamma                90
_cell_volume                     2973.61(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.52
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6572
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1301 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.8814.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.987
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            41911
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6844
_reflns_number_gt                5494
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+1.9519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6844
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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
O1 O 0.47892(7) 0.35930(11) 0.27270(7) 0.0206(2) Uani 1 1 d . . . . .
N1 N 0.29055(8) 0.35665(12) 0.16943(8) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.26431(9) 0.58175(15) 0.13115(9) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.20049(9) 0.59345(15) 0.15489(9) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.186007 0.521794 0.178551 0.023 Uiso 1 1 calc R U . . .
C3 C 0.15847(10) 0.70866(16) 0.14408(10) 0.0215(3) Uani 1 1 d . . . . .
H3 H 0.115868 0.716006 0.161121 0.026 Uiso 1 1 calc R U . . .
C4 C 0.17825(10) 0.81396(16) 0.10835(10) 0.0242(3) Uani 1 1 d . . . . .
H4 H 0.149882 0.893330 0.101889 0.029 Uiso 1 1 calc R U . . .
C5 C 0.23947(11) 0.80250(16) 0.08226(11) 0.0268(4) Uani 1 1 d . . . . .
H5 H 0.251869 0.873292 0.056229 0.032 Uiso 1 1 calc R U . . .
C6 C 0.28284(10) 0.68737(16) 0.09414(11) 0.0242(4) Uani 1 1 d . . . . .
H6 H 0.325370 0.680515 0.076962 0.029 Uiso 1 1 calc R U . . .
C7 C 0.31274(9) 0.46093(15) 0.14668(9) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.39188(9) 0.45158(15) 0.13658(10) 0.0197(3) Uani 1 1 d . . . . .
H8A H 0.379188 0.446482 0.076445 0.024 Uiso 1 1 calc R U . . .
H8B H 0.429535 0.525285 0.163365 0.024 Uiso 1 1 calc R U . . .
C9 C 0.42872(9) 0.32687(15) 0.18260(9) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.48415(9) 0.24964(16) 0.15518(10) 0.0211(3) Uani 1 1 d . . . . .
H10A H 0.521358 0.193366 0.202163 0.025 Uiso 1 1 calc R U . . .
H10B H 0.519540 0.309422 0.142335 0.025 Uiso 1 1 calc R U . . .
C11 C 0.43285(10) 0.16707(16) 0.07744(10) 0.0219(3) Uani 1 1 d . . . . .
H11A H 0.399015 0.223343 0.028913 0.026 Uiso 1 1 calc R U . . .
H11B H 0.470731 0.115962 0.062835 0.026 Uiso 1 1 calc R U . . .
C12 C 0.37561(10) 0.07702(15) 0.09464(10) 0.0214(3) Uani 1 1 d . . . . .
H12A H 0.408834 0.024790 0.145542 0.026 Uiso 1 1 calc R U . . .
H12B H 0.346828 0.017933 0.046311 0.026 Uiso 1 1 calc R U . . .
C13 C 0.31144(9) 0.15692(15) 0.10794(10) 0.0195(3) Uani 1 1 d . . . . .
H13A H 0.275830 0.203645 0.055200 0.023 Uiso 1 1 calc R U . . .
H13B H 0.275157 0.098589 0.120478 0.023 Uiso 1 1 calc R U . . .
C14 C 0.35213(9) 0.25364(15) 0.17982(9) 0.0170(3) Uani 1 1 d . . . . .
C15 C 0.38813(9) 0.19934(15) 0.26802(10) 0.0187(3) Uani 1 1 d . . . . .
C16 C 0.36100(10) 0.10371(15) 0.30394(10) 0.0221(3) Uani 1 1 d . . . . .
H16 H 0.313051 0.053790 0.270310 0.027 Uiso 1 1 calc R U . . .
C17 C 0.40576(11) 0.08266(17) 0.39048(11) 0.0273(4) Uani 1 1 d . . . . .
H17 H 0.388196 0.017669 0.416300 0.033 Uiso 1 1 calc R U . . .
C18 C 0.47580(11) 0.15586(17) 0.43929(10) 0.0279(4) Uani 1 1 d . . . . .
H18 H 0.505043 0.140447 0.498287 0.034 Uiso 1 1 calc R U . . .
C19 C 0.50446(10) 0.25159(17) 0.40401(10) 0.0244(4) Uani 1 1 d . . . . .
H19 H 0.552422 0.301572 0.437512 0.029 Uiso 1 1 calc R U . . .
C20 C 0.45944(10) 0.27002(15) 0.31767(10) 0.0194(3) Uani 1 1 d . . . . .
O2 O 0.01870(6) 0.91552(10) 0.22397(6) 0.0174(2) Uani 1 1 d . . . . .
N2 N 0.20727(8) 0.90626(12) 0.33745(8) 0.0161(3) Uani 1 1 d . . . . .
C21 C 0.22720(9) 0.67636(14) 0.36060(9) 0.0168(3) Uani 1 1 d . . . . .
C22 C 0.30398(9) 0.67437(15) 0.35901(10) 0.0209(3) Uani 1 1 d . . . . .
H22 H 0.329380 0.752723 0.355642 0.025 Uiso 1 1 calc R U . . .
C23 C 0.34314(10) 0.55809(16) 0.36234(10) 0.0229(3) Uani 1 1 d . . . . .
H23 H 0.395094 0.557334 0.360795 0.027 Uiso 1 1 calc R U . . .
C24 C 0.30701(10) 0.44256(15) 0.36793(10) 0.0213(3) Uani 1 1 d . . . . .
H24 H 0.333993 0.363235 0.369988 0.026 Uiso 1 1 calc R U . . .
C25 C 0.23140(10) 0.44416(15) 0.37045(10) 0.0217(3) Uani 1 1 d . . . . .
H25 H 0.206570 0.365694 0.374632 0.026 Uiso 1 1 calc R U . . .
C26 C 0.19178(10) 0.56020(15) 0.36689(10) 0.0189(3) Uani 1 1 d . . . . .
H26 H 0.139984 0.560445 0.368761 0.023 Uiso 1 1 calc R U . . .
C27 C 0.18094(9) 0.79792(14) 0.35047(9) 0.0166(3) Uani 1 1 d . . . . .
C28 C 0.09846(9) 0.80280(14) 0.35409(10) 0.0184(3) Uani 1 1 d . . . . .
H28A H 0.060591 0.733045 0.320207 0.022 Uiso 1 1 calc R U . . .
H28B H 0.106818 0.797064 0.412874 0.022 Uiso 1 1 calc R U . . .
C29 C 0.06552(9) 0.93354(14) 0.31617(9) 0.0157(3) Uani 1 1 d . . . . .
C30 C 0.00818(9) 1.00222(15) 0.34484(10) 0.0182(3) Uani 1 1 d . . . . .
H30A H -0.030266 0.938785 0.349817 0.022 Uiso 1 1 calc R U . . .
H30B H -0.025868 1.066185 0.301635 0.022 Uiso 1 1 calc R U . . .
C31 C 0.05677(10) 1.07036(16) 0.42960(10) 0.0211(3) Uani 1 1 d . . . . .
H31A H 0.017600 1.116463 0.444913 0.025 Uiso 1 1 calc R U . . .
H31B H 0.087497 1.006254 0.474168 0.025 Uiso 1 1 calc R U . . .
C32 C 0.11811(10) 1.16577(15) 0.42327(10) 0.0203(3) Uani 1 1 d . . . . .
H32A H 0.145639 1.216131 0.476102 0.024 Uiso 1 1 calc R U . . .
H32B H 0.087812 1.226285 0.376161 0.024 Uiso 1 1 calc R U . . .
C33 C 0.18380(9) 1.09266(14) 0.40822(9) 0.0171(3) Uani 1 1 d . . . . .
H33A H 0.216763 1.037846 0.457859 0.021 Uiso 1 1 calc R U . . .
H33B H 0.222362 1.155297 0.402729 0.021 Uiso 1 1 calc R U . . .
C34 C 0.14568(9) 1.00808(14) 0.32904(9) 0.0153(3) Uani 1 1 d . . . . .
C35 C 0.11580(9) 1.07424(14) 0.24453(9) 0.0150(3) Uani 1 1 d . . . . .
C36 C 0.14848(9) 1.17323(14) 0.21660(10) 0.0169(3) Uani 1 1 d . . . . .
H36 H 0.197535 1.217040 0.254754 0.020 Uiso 1 1 calc R U . . .
C37 C 0.10800(10) 1.20744(15) 0.13134(10) 0.0192(3) Uani 1 1 d . . . . .
H37 H 0.129475 1.275349 0.111324 0.023 Uiso 1 1 calc R U . . .
C38 C 0.03649(10) 1.14255(15) 0.07573(10) 0.0201(3) Uani 1 1 d . . . . .
H38 H 0.009712 1.166962 0.017992 0.024 Uiso 1 1 calc R U . . .
C39 C 0.00313(9) 1.04230(15) 0.10284(9) 0.0185(3) Uani 1 1 d . . . . .
H39 H -0.045532 0.997549 0.064777 0.022 Uiso 1 1 calc R U . . .
C40 C 0.04407(9) 1.01104(14) 0.18757(9) 0.0162(3) Uani 1 1 d . . . . .


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
O1 C9 1.4775(18) . ?
O1 C20 1.3734(19) . ?
N1 C7 1.2842(19) . ?
N1 C14 1.4924(19) . ?
C1 C2 1.402(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.482(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.521(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.516(2) . ?
C9 C10 1.527(2) . ?
C9 C14 1.558(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.530(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.525(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.529(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.527(2) . ?
C14 C15 1.510(2) . ?
C15 C16 1.388(2) . ?
C15 C20 1.391(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.397(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(2) . ?
O2 C29 1.4766(17) . ?
O2 C40 1.3745(18) . ?
N2 C27 1.2844(19) . ?
N2 C34 1.4918(18) . ?
C21 C22 1.398(2) . ?
C21 C26 1.395(2) . ?
C21 C27 1.480(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.519(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.514(2) . ?
C29 C30 1.525(2) . ?
C29 C34 1.562(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.530(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.528(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.531(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.533(2) . ?
C34 C35 1.513(2) . ?
C35 C36 1.387(2) . ?
C35 C40 1.391(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.398(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.390(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.396(2) . ?
C39 H39 0.9500 . ?
C39 C40 1.383(2) . ?

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
C20 O1 C9 106.70(11) . . ?
C7 N1 C14 108.87(12) . . ?
C2 C1 C7 120.83(13) . . ?
C6 C1 C2 118.74(14) . . ?
C6 C1 C7 120.42(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.43(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.40(15) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.74(15) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.10(15) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.55(15) . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C1 122.18(13) . . ?
N1 C7 C8 115.36(13) . . ?
C1 C7 C8 122.46(13) . . ?
C7 C8 H8A 111.5 . . ?
C7 C8 H8B 111.5 . . ?
H8A C8 H8B 109.4 . . ?
C9 C8 C7 101.14(12) . . ?
C9 C8 H8A 111.5 . . ?
C9 C8 H8B 111.5 . . ?
O1 C9 C8 106.98(12) . . ?
O1 C9 C10 107.63(12) . . ?
O1 C9 C14 103.85(11) . . ?
C8 C9 C10 117.77(13) . . ?
C8 C9 C14 103.78(12) . . ?
C10 C9 C14 115.70(13) . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 111.84(12) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.30(13) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C11 C12 C13 109.12(13) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.39(12) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
N1 C14 C9 104.58(12) . . ?
N1 C14 C13 108.90(12) . . ?
N1 C14 C15 109.80(12) . . ?
C13 C14 C9 115.29(12) . . ?
C15 C14 C9 101.37(12) . . ?
C15 C14 C13 116.12(13) . . ?
C16 C15 C14 132.41(15) . . ?
C16 C15 C20 120.23(15) . . ?
C20 C15 C14 107.28(13) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.42(16) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.54(16) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.78(15) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 H19 121.7 . . ?
C20 C19 C18 116.69(16) . . ?
C20 C19 H19 121.7 . . ?
O1 C20 C15 113.24(13) . . ?
O1 C20 C19 124.43(15) . . ?
C19 C20 C15 122.33(15) . . ?
C40 O2 C29 106.84(11) . . ?
C27 N2 C34 108.71(12) . . ?
C22 C21 C27 121.24(14) . . ?
C26 C21 C22 118.89(14) . . ?
C26 C21 C27 119.76(13) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.09(15) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.61(14) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.49(15) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.17(15) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.74(14) . . ?
C25 C26 H26 119.6 . . ?
N2 C27 C21 122.48(13) . . ?
N2 C27 C28 115.39(13) . . ?
C21 C27 C28 122.13(13) . . ?
C27 C28 H28A 111.4 . . ?
C27 C28 H28B 111.4 . . ?
H28A C28 H28B 109.3 . . ?
C29 C28 C27 101.71(12) . . ?
C29 C28 H28A 111.4 . . ?
C29 C28 H28B 111.4 . . ?
O2 C29 C28 106.91(11) . . ?
O2 C29 C30 107.61(11) . . ?
O2 C29 C34 104.23(11) . . ?
C28 C29 C30 117.32(12) . . ?
C28 C29 C34 103.43(11) . . ?
C30 C29 C34 116.27(12) . . ?
C29 C30 H30A 109.2 . . ?
C29 C30 H30B 109.2 . . ?
C29 C30 C31 112.21(12) . . ?
H30A C30 H30B 107.9 . . ?
C31 C30 H30A 109.2 . . ?
C31 C30 H30B 109.2 . . ?
C30 C31 H31A 109.8 . . ?
C30 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?
C32 C31 C30 109.55(12) . . ?
C32 C31 H31A 109.8 . . ?
C32 C31 H31B 109.8 . . ?
C31 C32 H32A 109.8 . . ?
C31 C32 H32B 109.8 . . ?
C31 C32 C33 109.57(13) . . ?
H32A C32 H32B 108.2 . . ?
C33 C32 H32A 109.8 . . ?
C33 C32 H32B 109.8 . . ?
C32 C33 H33A 109.0 . . ?
C32 C33 H33B 109.0 . . ?
C32 C33 C34 112.91(12) . . ?
H33A C33 H33B 107.8 . . ?
C34 C33 H33A 109.0 . . ?
C34 C33 H33B 109.0 . . ?
N2 C34 C29 105.02(11) . . ?
N2 C34 C33 108.37(11) . . ?
N2 C34 C35 109.41(11) . . ?
C33 C34 C29 114.50(12) . . ?
C35 C34 C29 101.27(11) . . ?
C35 C34 C33 117.47(12) . . ?
C36 C35 C34 132.73(14) . . ?
C36 C35 C40 119.64(14) . . ?
C40 C35 C34 107.49(13) . . ?
C35 C36 H36 120.6 . . ?
C35 C36 C37 118.89(14) . . ?
C37 C36 H36 120.6 . . ?
C36 C37 H37 119.9 . . ?
C38 C37 C36 120.29(14) . . ?
C38 C37 H37 119.9 . . ?
C37 C38 H38 119.3 . . ?
C37 C38 C39 121.47(14) . . ?
C39 C38 H38 119.3 . . ?
C38 C39 H39 121.5 . . ?
C40 C39 C38 117.04(14) . . ?
C40 C39 H39 121.5 . . ?
O2 C40 C35 113.34(13) . . ?
O2 C40 C39 123.99(13) . . ?
C39 C40 C35 122.68(14) . . ?

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
O1 C9 C10 C11 157.29(12) . . . . ?
O1 C9 C14 N1 87.68(13) . . . . ?
O1 C9 C14 C13 -152.77(12) . . . . ?
O1 C9 C14 C15 -26.49(14) . . . . ?
N1 C7 C8 C9 -15.73(17) . . . . ?
N1 C14 C15 C16 85.3(2) . . . . ?
N1 C14 C15 C20 -91.15(14) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C1 C7 C8 C9 164.45(13) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C2 C1 C7 N1 11.4(2) . . . . ?
C2 C1 C7 C8 -168.84(14) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C6 C1 C2 C3 -1.9(2) . . . . ?
C6 C1 C7 N1 -170.09(15) . . . . ?
C6 C1 C7 C8 9.7(2) . . . . ?
C7 N1 C14 C9 15.13(15) . . . . ?
C7 N1 C14 C13 -108.63(14) . . . . ?
C7 N1 C14 C15 123.21(14) . . . . ?
C7 C1 C2 C3 176.70(14) . . . . ?
C7 C1 C6 C5 -177.67(15) . . . . ?
C7 C8 C9 O1 -86.43(13) . . . . ?
C7 C8 C9 C10 152.32(13) . . . . ?
C7 C8 C9 C14 23.00(14) . . . . ?
C8 C9 C10 C11 -81.80(17) . . . . ?
C8 C9 C14 N1 -24.05(14) . . . . ?
C8 C9 C14 C13 95.50(15) . . . . ?
C8 C9 C14 C15 -138.21(12) . . . . ?
C9 O1 C20 C15 -14.04(16) . . . . ?
C9 O1 C20 C19 166.90(14) . . . . ?
C9 C10 C11 C12 -57.08(17) . . . . ?
C9 C14 C15 C16 -164.45(16) . . . . ?
C9 C14 C15 C20 19.06(15) . . . . ?
C10 C9 C14 N1 -154.62(12) . . . . ?
C10 C9 C14 C13 -35.07(18) . . . . ?
C10 C9 C14 C15 91.21(14) . . . . ?
C10 C11 C12 C13 65.17(16) . . . . ?
C11 C12 C13 C14 -57.45(17) . . . . ?
C12 C13 C14 N1 159.75(12) . . . . ?
C12 C13 C14 C9 42.61(18) . . . . ?
C12 C13 C14 C15 -75.72(17) . . . . ?
C13 C14 C15 C16 -38.7(2) . . . . ?
C13 C14 C15 C20 144.79(13) . . . . ?
C14 N1 C7 C1 -179.93(13) . . . . ?
C14 N1 C7 C8 0.25(17) . . . . ?
C14 C9 C10 C11 41.72(18) . . . . ?
C14 C15 C16 C17 -174.81(15) . . . . ?
C14 C15 C20 O1 -4.09(17) . . . . ?
C14 C15 C20 C19 175.00(14) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C15 C20 O1 178.91(13) . . . . ?
C16 C15 C20 C19 -2.0(2) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C19 C20 O1 -179.72(14) . . . . ?
C18 C19 C20 C15 1.3(2) . . . . ?
C20 O1 C9 C8 134.71(12) . . . . ?
C20 O1 C9 C10 -97.83(14) . . . . ?
C20 O1 C9 C14 25.33(14) . . . . ?
C20 C15 C16 C17 1.3(2) . . . . ?
O2 C29 C30 C31 -158.53(12) . . . . ?
O2 C29 C34 N2 -88.67(12) . . . . ?
O2 C29 C34 C33 152.59(12) . . . . ?
O2 C29 C34 C35 25.17(13) . . . . ?
N2 C27 C28 C29 15.22(17) . . . . ?
N2 C34 C35 C36 -83.22(19) . . . . ?
N2 C34 C35 C40 92.50(14) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C21 C27 C28 C29 -164.30(13) . . . . ?
C22 C21 C26 C25 -0.8(2) . . . . ?
C22 C21 C27 N2 2.0(2) . . . . ?
C22 C21 C27 C28 -178.50(14) . . . . ?
C22 C23 C24 C25 -0.2(2) . . . . ?
C23 C24 C25 C26 0.4(2) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?
C26 C21 C22 C23 1.0(2) . . . . ?
C26 C21 C27 N2 -174.15(15) . . . . ?
C26 C21 C27 C28 5.3(2) . . . . ?
C27 N2 C34 C29 -14.46(15) . . . . ?
C27 N2 C34 C33 108.33(14) . . . . ?
C27 N2 C34 C35 -122.46(13) . . . . ?
C27 C21 C22 C23 -175.20(14) . . . . ?
C27 C21 C26 C25 175.44(14) . . . . ?
C27 C28 C29 O2 87.66(13) . . . . ?
C27 C28 C29 C30 -151.48(13) . . . . ?
C27 C28 C29 C34 -22.02(14) . . . . ?
C28 C29 C30 C31 80.98(17) . . . . ?
C28 C29 C34 N2 22.98(14) . . . . ?
C28 C29 C34 C33 -95.75(14) . . . . ?
C28 C29 C34 C35 136.83(12) . . . . ?
C29 O2 C40 C35 13.49(16) . . . . ?
C29 O2 C40 C39 -166.59(13) . . . . ?
C29 C30 C31 C32 57.23(17) . . . . ?
C29 C34 C35 C36 166.27(15) . . . . ?
C29 C34 C35 C40 -18.01(15) . . . . ?
C30 C29 C34 N2 153.08(12) . . . . ?
C30 C29 C34 C33 34.34(18) . . . . ?
C30 C29 C34 C35 -93.07(14) . . . . ?
C30 C31 C32 C33 -64.98(16) . . . . ?
C31 C32 C33 C34 57.25(17) . . . . ?
C32 C33 C34 N2 -158.34(12) . . . . ?
C32 C33 C34 C29 -41.51(17) . . . . ?
C32 C33 C34 C35 77.10(16) . . . . ?
C33 C34 C35 C36 40.8(2) . . . . ?
C33 C34 C35 C40 -143.47(13) . . . . ?
C34 N2 C27 C21 179.20(13) . . . . ?
C34 N2 C27 C28 -0.31(18) . . . . ?
C34 C29 C30 C31 -42.15(18) . . . . ?
C34 C35 C36 C37 175.52(15) . . . . ?
C34 C35 C40 O2 3.77(16) . . . . ?
C34 C35 C40 C39 -176.15(13) . . . . ?
C35 C36 C37 C38 -0.3(2) . . . . ?
C36 C35 C40 O2 -179.84(12) . . . . ?
C36 C35 C40 C39 0.2(2) . . . . ?
C36 C37 C38 C39 0.0(2) . . . . ?
C37 C38 C39 C40 0.4(2) . . . . ?
C38 C39 C40 O2 179.53(13) . . . . ?
C38 C39 C40 C35 -0.6(2) . . . . ?
C40 O2 C29 C28 -133.33(12) . . . . ?
C40 O2 C29 C30 99.82(13) . . . . ?
C40 O2 C29 C34 -24.21(14) . . . . ?
C40 C35 C36 C37 0.2(2) . . . . ?

