# Supplementary Information (SI) for Organic & Biomolecular 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_ta4151
_database_code_depnum_ccdc_archive 'CCDC 2395115'
loop_
_audit_author_name
_audit_author_address
'Guangwu Zhang'
;Henan University
China
;
_audit_update_record             
;
2024-10-31 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_audit_creation_date             2024-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 N2'
_chemical_formula_sum            'C36 H36 N2'
_chemical_formula_weight         496.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H22O5N1
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   28.4509(12)
_cell_length_b                   9.1830(3)
_cell_length_c                   11.7236(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.082(5)
_cell_angle_gamma                90
_cell_volume                     2774.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9410
_cell_measurement_theta_min      4.1280
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5549
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         3.430
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -17.00   1.00    1.00    --  -33.50 -37.00  90.00   86
  2  ω    -62.00 -36.00   1.00    1.00    --  -33.50 178.00-180.00   26
  3  ω    -71.00 -17.00   1.00    1.00    --  -33.50 -57.00 -30.00   54
  4  ω     62.00 108.00   1.00    1.00    --   36.47 178.00 -30.00   46
  5  ω     70.00  97.00   1.00    1.00    --   36.47 178.00   0.00   27
  6  ω     62.00  92.00   1.00    1.00    --   36.47 178.00-180.00   30
  7  ω     12.00  54.00   1.00    1.00    --   36.47 -37.00 -90.00   42
  8  ω    -10.00  54.00   1.00    1.00    --   36.47 -57.00   0.00   64
  9  ω    -30.00   0.00   1.00    1.00    --   36.47 -37.00 -90.00   30
 10  ω     61.00  97.00   1.00    1.00    --   36.47 178.00 -60.00   36
 11  ω     41.00  97.00   1.00    3.00    --  108.00 -77.00  60.00   56
 12  ω     39.00 128.00   1.00    3.00    --  108.00 -45.00 -30.00   89
 13  ω     52.00  77.00   1.00    3.00    --  108.00-111.00   0.00   25
 14  ω    103.00 170.00   1.00    3.00    --  108.00  77.00 -30.00   67
 15  ω     84.00 110.00   1.00    3.00    --  108.00 -30.00  60.00   26
 16  ω     38.00 127.00   1.00    3.00    --  108.00 -45.00-180.00   89
 17  ω     37.00  62.00   1.00    3.00    --  108.00 -30.00  60.00   25
 18  ω    101.00 138.00   1.00    3.00    --  108.00  77.00  90.00   37
 19  ω     91.00 175.00   1.00    3.00    --  108.00   0.00-120.00   84
 20  ω     44.00  70.00   1.00    3.00    --  108.00-104.00  49.00   26
 21  ω     43.00  75.00   1.00    3.00    --  108.00   0.00-120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0094588000
_diffrn_orient_matrix_UB_12      0.0718262000
_diffrn_orient_matrix_UB_13      -0.1071733000
_diffrn_orient_matrix_UB_21      -0.0569702000
_diffrn_orient_matrix_UB_22      0.0511177000
_diffrn_orient_matrix_UB_23      -0.0615796000
_diffrn_orient_matrix_UB_31      0.0156023000
_diffrn_orient_matrix_UB_32      0.1426682000
_diffrn_orient_matrix_UB_33      0.0759238000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2022
_reflns_number_total             2466
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.040
_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)+(0.0872P)²+0.3981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1536
_refine_special_details          ?
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.39918(5) 0.41798(15) 0.52006(13) 0.0420(4) Uani 1 1 d . . . . .
C1 C 0.43362(6) 0.36010(19) 0.46644(15) 0.0413(4) Uani 1 1 d . . . . .
H1A H 0.4424 0.4350 0.4205 0.050 Uiso 1 1 calc R . . . .
H1B H 0.4175 0.2792 0.4102 0.050 Uiso 1 1 calc R . . . .
C2 C 0.48117(6) 0.31053(17) 0.58020(14) 0.0371(4) Uani 1 1 d . . . . .
C3 C 0.48011(6) 0.36850(17) 0.68407(14) 0.0378(4) Uani 1 1 d . . . . .
C4 C 0.43230(6) 0.4603(2) 0.64975(15) 0.0435(4) Uani 1 1 d . . . . .
H4A H 0.4155 0.4397 0.7048 0.052 Uiso 1 1 calc R . . . .
H4B H 0.4407 0.5631 0.6550 0.052 Uiso 1 1 calc R . . . .
C5 C 0.52051(6) 0.21744(18) 0.56620(14) 0.0374(4) Uani 1 1 d . . . . .
C6 C 0.56239(6) 0.15769(19) 0.66930(15) 0.0411(4) Uani 1 1 d . . . . .
H6 H 0.5654 0.1766 0.7501 0.049 Uiso 1 1 calc R . . . .
C7 C 0.59946(7) 0.07129(19) 0.65495(17) 0.0450(4) Uani 1 1 d . . . . .
C8 C 0.59445(8) 0.0419(2) 0.53418(19) 0.0524(5) Uani 1 1 d . . . . .
H8 H 0.6190 -0.0160 0.5229 0.063 Uiso 1 1 calc R . . . .
C9 C 0.55330(8) 0.0980(2) 0.43085(17) 0.0545(5) Uani 1 1 d . . . . .
H9 H 0.5501 0.0771 0.3503 0.065 Uiso 1 1 calc R . . . .
C10 C 0.51670(7) 0.1853(2) 0.44608(16) 0.0464(4) Uani 1 1 d . . . . .
H10 H 0.4893 0.2230 0.3756 0.056 Uiso 1 1 calc R . . . .
C11 C 0.36563(7) 0.5355(2) 0.44659(18) 0.0500(5) Uani 1 1 d . . . . .
H11A H 0.3869 0.6112 0.4346 0.060 Uiso 1 1 calc R . . . .
H11B H 0.3480 0.5773 0.4938 0.060 Uiso 1 1 calc R . . . .
C12 C 0.32567(6) 0.4872(2) 0.31960(16) 0.0436(4) Uani 1 1 d . . . . .
C13 C 0.29967(8) 0.3566(2) 0.30377(19) 0.0559(5) Uani 1 1 d . . . . .
H13 H 0.3081 0.2941 0.3721 0.067 Uiso 1 1 calc R . . . .
C14 C 0.26120(9) 0.3169(3) 0.1878(2) 0.0689(6) Uani 1 1 d . . . . .
H14 H 0.2444 0.2280 0.1786 0.083 Uiso 1 1 calc R . . . .
C15 C 0.24786(9) 0.4086(3) 0.0864(2) 0.0719(7) Uani 1 1 d . . . . .
H15 H 0.2214 0.3831 0.0090 0.086 Uiso 1 1 calc R . . . .
C16 C 0.27357(10) 0.5374(3) 0.0997(2) 0.0738(7) Uani 1 1 d . . . . .
H16 H 0.2649 0.5993 0.0310 0.089 Uiso 1 1 calc R . . . .
C17 C 0.31277(8) 0.5765(2) 0.21589(19) 0.0584(5) Uani 1 1 d . . . . .
H17 H 0.3305 0.6637 0.2237 0.070 Uiso 1 1 calc R . . . .
C18 C 0.64419(8) 0.0091(3) 0.7681(2) 0.0604(6) Uani 1 1 d . . . . .
H18A H 0.6377 -0.0919 0.7772 0.091 Uiso 1 1 calc GR . . . .
H18B H 0.6478 0.0613 0.8423 0.091 Uiso 1 1 calc GR . . . .
H18C H 0.6756 0.0182 0.7568 0.091 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.469(2) . ?
N1 C4 1.461(2) . ?
N1 C11 1.456(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.512(2) . ?
C2 C3 1.341(2) . ?
C2 C5 1.472(2) . ?
C3 C3 1.479(3) 2_656 ?
C3 C4 1.503(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.400(2) . ?
C5 C10 1.397(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(2) . ?
C7 C8 1.388(3) . ?
C7 C18 1.508(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.507(2) . ?
C12 C13 1.380(3) . ?
C12 C17 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C4 N1 C1 106.77(13) . . ?
C11 N1 C1 113.81(14) . . ?
C11 N1 C4 112.98(14) . . ?
N1 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
N1 C1 C2 103.95(12) . . ?
H1A C1 H1B 109.0 . . ?
C2 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
C3 C2 C1 108.98(14) . . ?
C3 C2 C5 130.00(15) . . ?
C5 C2 C1 120.99(14) . . ?
C2 C3 C3 130.34(17) . 2_656 ?
C2 C3 C4 110.23(14) . . ?
C3 C3 C4 118.99(14) 2_656 . ?
N1 C4 C3 103.93(13) . . ?
N1 C4 H4A 111.0 . . ?
N1 C4 H4B 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C6 C5 C2 122.71(14) . . ?
C10 C5 C2 119.82(15) . . ?
C10 C5 C6 117.47(15) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.17(15) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 118.75(16) . . ?
C6 C7 C18 120.80(17) . . ?
C8 C7 C18 120.45(17) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.34(17) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.54(17) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.74(16) . . ?
C9 C10 H10 119.6 . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
N1 C11 C12 113.42(15) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 121.70(17) . . ?
C13 C12 C17 118.06(18) . . ?
C17 C12 C11 120.20(18) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.8(2) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C1 C2 C3 -15.08(18) . . . . ?
N1 C1 C2 C5 166.81(14) . . . . ?
N1 C11 C12 C13 40.5(2) . . . . ?
N1 C11 C12 C17 -141.84(18) . . . . ?
C1 N1 C4 C3 -23.90(17) . . . . ?
C1 N1 C11 C12 66.9(2) . . . . ?
C1 C2 C3 C3 -171.84(13) . . . 2_656 ?
C1 C2 C3 C4 0.25(19) . . . . ?
C1 C2 C5 C6 -173.62(15) . . . . ?
C1 C2 C5 C10 6.1(2) . . . . ?
C2 C3 C4 N1 14.76(18) . . . . ?
C2 C5 C6 C7 -179.38(16) . . . . ?
C2 C5 C10 C9 179.98(16) . . . . ?
C3 C2 C5 C6 8.7(3) . . . . ?
C3 C2 C5 C10 -171.52(17) . . . . ?
C3 C3 C4 N1 -172.13(13) 2_656 . . . ?
C4 N1 C1 C2 24.08(17) . . . . ?
C4 N1 C11 C12 -171.08(15) . . . . ?
C5 C2 C3 C3 6.0(3) . . . 2_656 ?
C5 C2 C3 C4 178.13(16) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C18 179.79(17) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C5 -0.4(3) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C11 N1 C1 C2 149.44(13) . . . . ?
C11 N1 C4 C3 -149.76(15) . . . . ?
C11 C12 C13 C14 176.74(19) . . . . ?
C11 C12 C17 C16 -175.85(19) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C12 C17 C16 1.9(3) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C12 -1.1(4) . . . . ?
C17 C12 C13 C14 -1.0(3) . . . . ?
C18 C7 C8 C9 179.52(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.167
_oxdiff_exptl_absorpt_empirical_full_min 0.863
####################################################################### 
# 
# 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_ta4502a
_database_code_depnum_ccdc_archive 'CCDC 2395116'
loop_
_audit_author_name
_audit_author_address
'Guangwu Zhang'
;Henan University
China
;
_audit_update_record             
;
2024-10-31 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_audit_creation_date             2024-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 N2'
_chemical_formula_sum            'C36 H36 N2'
_chemical_formula_weight         496.67
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H22N1
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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'

_cell_length_a                   26.6157(14)
_cell_length_b                   9.4617(5)
_cell_length_c                   11.3780(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.543(4)
_cell_angle_gamma                90
_cell_volume                     2833.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7470
_cell_measurement_theta_min      3.3583
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11618
_diffrn_reflns_point_group_measured_fraction_full 0.869
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.033
_diffrn_reflns_theta_min         3.358
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    2.00    --  -33.50 -57.00 120.00   87
  2  ω    -61.00  23.00   1.00    2.00    --  -33.50  77.00 -90.00   84
  3  ω   -107.00 -65.00   1.00    2.00    --  -33.50 178.00  60.00   42
  4  ω     76.00 103.00   1.00    2.00    --   36.47  57.00 -90.00   27
  5  ω    -25.00  68.00   1.00    2.00    --   36.47 -19.00 -90.00   93
  6  ω     46.00 129.00   1.00    7.50    --  108.00 -30.00 -90.00   83
  7  ω    114.00 176.00   1.00    7.50    --  108.00 111.00-120.00   62
  8  ω     88.00 168.00   1.00    7.50    --  108.00  61.00 -90.00   80
  9  ω    140.00 175.00   1.00    7.50    --  108.00 111.00  30.00   35
 10  ω    126.00 152.00   1.00    7.50    --  108.00 111.00 150.00   26
 11  ω     41.00  93.00   1.00    7.50    --  108.00 -94.00  60.00   52
 12  ω     41.00  82.00   1.00    7.50    --  108.00 -94.00-180.00   41
 13  ω    116.00 142.00   1.00    7.50    --  108.00  76.00-123.00   26
 14  ω    106.00 136.00   1.00    7.50    --  108.00 111.00 -60.00   30
 15  ω     61.00 124.00   1.00    7.50    --  108.00 -45.00 120.00   63
 16  ω     68.00 104.00   1.00    7.50    --  108.00-111.00 -30.00   36
 17  ω    -29.00  21.00   1.00    2.50    --  -33.50  37.00  90.00   50
 18  ω     44.00  76.00   1.00    2.50    --   36.47-131.00  46.00   32
 19  ω     69.00  97.00   1.00    2.50    --   36.47-138.00-128.00   28
 20  ω    -16.00  14.00   1.00    2.50    --   36.47 -77.00-150.00   30
 21  ω     70.00 103.00   1.00    2.50    --   36.47  37.00-120.00   33
 22  ω     51.00  76.00   1.00    2.50    --   36.47 -99.00  30.00   25
 23  ω     11.00  37.00   1.00    2.50    --   36.47 -99.00  30.00   26
 24  ω     70.00  96.00   1.00    2.50    --   36.47 178.00-180.00   26
 25  ω    105.00 130.00   1.00    7.50    --  108.00 111.00 -30.00   25
 26  ω     67.00  93.00   1.00    7.50    --  108.00 -45.00-150.00   26
 27  ω     75.00 109.00   1.00    7.50    --  108.00-111.00-180.00   34
 28  ω     65.00  97.00   1.00    7.50    --  108.00 -94.00  90.00   32
 29  ω    103.00 177.00   1.00    7.50    --  108.00  77.00-150.00   74
 30  ω     81.00 107.00   1.00    7.50    --  108.00-111.00 -90.00   26
 31  ω    127.00 158.00   1.00    7.50    --  108.00  77.00  30.00   31
 32  ω     44.00  70.00   1.00    7.50    --  108.00-111.00-180.00   26
 33  ω    102.00 153.00   1.00    7.50    --  108.00  77.00 120.00   51
 34  ω     56.00 102.00   1.00    7.50    --  108.00-111.00  30.00   46
 35  ω     43.00  95.00   1.00    7.50    --  108.00 -61.00-180.00   52
 36  ω     92.00 145.00   1.00    7.50    --  108.00  30.00-180.00   53
 37  ω    105.00 162.00   1.00    7.50    --  108.00 111.00  90.00   57
 38  ω     69.00  94.00   1.00    2.50    --   36.47-131.00  46.00   25
 39  ω    102.00 128.00   1.00    7.50    --  108.00  77.00  30.00   26
 40  ω     88.00 127.00   1.00    7.50    --  108.00  45.00  90.00   39
 41  ω     74.00 115.00   1.00    7.50    --  108.00 -76.00 109.00   41
 42  ω     96.00 144.00   1.00    7.50    --  108.00  30.00-150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0082062000
_diffrn_orient_matrix_UB_12      0.1348287000
_diffrn_orient_matrix_UB_13      0.0764852000
_diffrn_orient_matrix_UB_21      0.0579463000
_diffrn_orient_matrix_UB_22      -0.0182781000
_diffrn_orient_matrix_UB_23      0.0087974000
_diffrn_orient_matrix_UB_31      -0.0004916000
_diffrn_orient_matrix_UB_32      0.0895754000
_diffrn_orient_matrix_UB_33      -0.1131793000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.737
_reflns_Friedel_fraction_max     0.716
_reflns_number_gt                3993
_reflns_number_total             4681
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       0.00116(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4681
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.050
_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)+(0.0727P)²+0.0781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1393
_refine_special_details          ?
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C11(H11A,H11B), C19(H19A,H19B), C22(H22A,H22B),
 C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C24(H24), C25(H25), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.79109(12) 0.3882(3) 0.7842(3) 0.0514(7) Uani 1 1 d . . . . .
N2 N 0.59741(11) 0.4100(3) 0.4420(3) 0.0480(6) Uani 1 1 d . . . . .
C1 C 0.76033(15) 0.4451(4) 0.6775(3) 0.0511(8) Uani 1 1 d . . . . .
H1A H 0.7773 0.4332 0.6084 0.061 Uiso 1 1 calc R . . . .
H1B H 0.7532 0.5446 0.6871 0.061 Uiso 1 1 calc R . . . .
C2 C 0.71232(14) 0.3581(4) 0.6667(3) 0.0474(7) Uani 1 1 d . . . . .
C3 C 0.70902(13) 0.2921(4) 0.7700(3) 0.0449(7) Uani 1 1 d . . . . .
C4 C 0.75552(14) 0.3306(4) 0.8576(3) 0.0524(8) Uani 1 1 d . . . . .
H4A H 0.7472 0.4005 0.9140 0.063 Uiso 1 1 calc R . . . .
H4B H 0.7696 0.2479 0.9007 0.063 Uiso 1 1 calc R . . . .
C5 C 0.66900(13) 0.2038(4) 0.8054(3) 0.0452(7) Uani 1 1 d . . . . .
C6 C 0.67000(14) 0.1632(4) 0.9243(3) 0.0547(9) Uani 1 1 d . . . . .
H6 H 0.6971 0.1913 0.9806 0.066 Uiso 1 1 calc R . . . .
C7 C 0.63192(16) 0.0828(4) 0.9597(3) 0.0594(9) Uani 1 1 d . . . . .
H7 H 0.6340 0.0583 1.0394 0.071 Uiso 1 1 calc R . . . .
C8 C 0.59072(15) 0.0373(4) 0.8809(3) 0.0531(8) Uani 1 1 d . . . . .
C9 C 0.58942(15) 0.0753(4) 0.7628(3) 0.0575(9) Uani 1 1 d . . . . .
H9 H 0.5621 0.0462 0.7074 0.069 Uiso 1 1 calc R . . . .
C10 C 0.62768(15) 0.1553(4) 0.7251(3) 0.0531(8) Uani 1 1 d . . . . .
H10 H 0.6258 0.1771 0.6449 0.064 Uiso 1 1 calc R . . . .
C11 C 0.82683(16) 0.4882(5) 0.8478(4) 0.0646(10) Uani 1 1 d . . . . .
H11A H 0.8424 0.4447 0.9215 0.078 Uiso 1 1 calc R . . . .
H11B H 0.8081 0.5703 0.8683 0.078 Uiso 1 1 calc R . . . .
C12 C 0.86828(15) 0.5372(4) 0.7810(3) 0.0565(9) Uani 1 1 d . . . . .
C13 C 0.89373(17) 0.6610(5) 0.8156(4) 0.0685(10) Uani 1 1 d . . . . .
H13 H 0.8845 0.7129 0.8784 0.082 Uiso 1 1 calc R . . . .
C14 C 0.93282(19) 0.7089(5) 0.7578(5) 0.0830(13) Uani 1 1 d . . . . .
H14 H 0.9501 0.7915 0.7831 0.100 Uiso 1 1 calc R . . . .
C15 C 0.94612(18) 0.6348(6) 0.6635(5) 0.0798(13) Uani 1 1 d . . . . .
H15 H 0.9720 0.6677 0.6241 0.096 Uiso 1 1 calc R . . . .
C16 C 0.92111(16) 0.5118(5) 0.6275(4) 0.0724(11) Uani 1 1 d . . . . .
H16 H 0.9298 0.4620 0.5630 0.087 Uiso 1 1 calc R . . . .
C17 C 0.88283(16) 0.4616(5) 0.6873(4) 0.0641(10) Uani 1 1 d . . . . .
H17 H 0.8668 0.3765 0.6642 0.077 Uiso 1 1 calc R . . . .
C18 C 0.54830(18) -0.0466(5) 0.9196(4) 0.0652(10) Uani 1 1 d . . . . .
H18A H 0.5571 -0.1451 0.9224 0.098 Uiso 1 1 calc GR . . . .
H18B H 0.5178 -0.0327 0.8640 0.098 Uiso 1 1 calc GR . . . .
H18C H 0.5428 -0.0159 0.9970 0.098 Uiso 1 1 calc GR . . . .
C19 C 0.62862(14) 0.4524(4) 0.5526(3) 0.0514(8) Uani 1 1 d . . . . .
H19A H 0.6114 0.4336 0.6203 0.062 Uiso 1 1 calc R . . . .
H19B H 0.6371 0.5520 0.5515 0.062 Uiso 1 1 calc R . . . .
C20 C 0.67537(13) 0.3622(4) 0.5563(3) 0.0440(7) Uani 1 1 d . . . . .
C21 C 0.67787(13) 0.3092(4) 0.4487(3) 0.0439(7) Uani 1 1 d . . . . .
C22 C 0.63237(14) 0.3591(4) 0.3634(3) 0.0505(8) Uani 1 1 d . . . . .
H22A H 0.6416 0.4344 0.3130 0.061 Uiso 1 1 calc R . . . .
H22B H 0.6174 0.2821 0.3138 0.061 Uiso 1 1 calc R . . . .
C23 C 0.71719(13) 0.2207(4) 0.4080(3) 0.0453(7) Uani 1 1 d . . . . .
C24 C 0.75763(15) 0.1633(4) 0.4858(3) 0.0543(8) Uani 1 1 d . . . . .
H24 H 0.7594 0.1781 0.5671 0.065 Uiso 1 1 calc R . . . .
C25 C 0.79507(15) 0.0850(5) 0.4439(3) 0.0585(9) Uani 1 1 d . . . . .
H25 H 0.8217 0.0492 0.4978 0.070 Uiso 1 1 calc R . . . .
C26 C 0.79399(15) 0.0583(4) 0.3241(3) 0.0529(8) Uani 1 1 d . . . . .
C27 C 0.75349(16) 0.1117(5) 0.2470(3) 0.0592(9) Uani 1 1 d . . . . .
H27 H 0.7514 0.0942 0.1659 0.071 Uiso 1 1 calc R . . . .
C28 C 0.71570(15) 0.1910(4) 0.2880(3) 0.0570(9) Uani 1 1 d . . . . .
H28 H 0.6888 0.2250 0.2339 0.068 Uiso 1 1 calc R . . . .
C29 C 0.56204(14) 0.5183(4) 0.3887(3) 0.0574(9) Uani 1 1 d . . . . .
H29A H 0.5449 0.4852 0.3125 0.069 Uiso 1 1 calc R . . . .
H29B H 0.5807 0.6034 0.3752 0.069 Uiso 1 1 calc R . . . .
C30 C 0.52347(14) 0.5515(4) 0.4683(3) 0.0554(9) Uani 1 1 d . . . . .
C31 C 0.52783(17) 0.6702(5) 0.5403(4) 0.0669(10) Uani 1 1 d . . . . .
H31 H 0.5549 0.7319 0.5379 0.080 Uiso 1 1 calc R . . . .
C32 C 0.4929(2) 0.6992(6) 0.6156(5) 0.0824(13) Uani 1 1 d . . . . .
H32 H 0.4968 0.7792 0.6635 0.099 Uiso 1 1 calc R . . . .
C33 C 0.4532(2) 0.6124(6) 0.6200(5) 0.0846(14) Uani 1 1 d . . . . .
H33 H 0.4298 0.6325 0.6707 0.101 Uiso 1 1 calc R . . . .
C34 C 0.44733(18) 0.4936(6) 0.5494(5) 0.0842(14) Uani 1 1 d . . . . .
H34 H 0.4197 0.4341 0.5518 0.101 Uiso 1 1 calc R . . . .
C35 C 0.48267(16) 0.4625(5) 0.4746(4) 0.0698(11) Uani 1 1 d . . . . .
H35 H 0.4789 0.3811 0.4283 0.084 Uiso 1 1 calc R . . . .
C36 C 0.83542(18) -0.0257(5) 0.2795(4) 0.0685(11) Uani 1 1 d . . . . .
H36A H 0.8217 -0.1132 0.2461 0.103 Uiso 1 1 calc GR . . . .
H36B H 0.8620 -0.0449 0.3443 0.103 Uiso 1 1 calc GR . . . .
H36C H 0.8490 0.0276 0.2196 0.103 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.461(4) . ?
N1 C4 1.458(5) . ?
N1 C11 1.456(5) . ?
N2 C19 1.457(4) . ?
N2 C22 1.465(5) . ?
N2 C29 1.461(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.510(5) . ?
C2 C3 1.345(5) . ?
C2 C20 1.476(4) . ?
C3 C4 1.514(5) . ?
C3 C5 1.456(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.404(5) . ?
C5 C10 1.399(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(6) . ?
C8 C9 1.385(5) . ?
C8 C18 1.499(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(6) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.503(6) . ?
C12 C13 1.381(6) . ?
C12 C17 1.386(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(6) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.504(5) . ?
C20 C21 1.334(5) . ?
C21 C22 1.511(4) . ?
C21 C23 1.468(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.398(5) . ?
C23 C28 1.388(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.383(5) . ?
C26 C27 1.381(6) . ?
C26 C36 1.507(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(5) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.500(6) . ?
C30 C31 1.385(6) . ?
C30 C35 1.384(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.383(6) . ?
C32 H32 0.9300 . ?
C32 C33 1.344(8) . ?
C33 H33 0.9300 . ?
C33 C34 1.377(8) . ?
C34 H34 0.9300 . ?
C34 C35 1.391(7) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

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
C4 N1 C1 106.4(3) . . ?
C11 N1 C1 114.7(3) . . ?
C11 N1 C4 112.9(3) . . ?
C19 N2 C22 106.6(3) . . ?
C19 N2 C29 114.5(3) . . ?
C29 N2 C22 114.0(3) . . ?
N1 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
N1 C1 C2 103.3(3) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C3 C2 C1 110.3(3) . . ?
C3 C2 C20 129.3(3) . . ?
C20 C2 C1 120.3(3) . . ?
C2 C3 C4 108.1(3) . . ?
C2 C3 C5 130.8(3) . . ?
C5 C3 C4 121.1(3) . . ?
N1 C4 C3 104.5(3) . . ?
N1 C4 H4A 110.9 . . ?
N1 C4 H4B 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C6 C5 C3 120.9(3) . . ?
C10 C5 C3 123.0(3) . . ?
C10 C5 C6 116.1(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C8 122.2(3) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C9 116.9(4) . . ?
C7 C8 C18 122.4(3) . . ?
C9 C8 C18 120.7(4) . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.3(3) . . ?
C9 C10 H10 119.4 . . ?
N1 C11 H11A 108.5 . . ?
N1 C11 H11B 108.5 . . ?
N1 C11 C12 115.0(3) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 C17 118.4(4) . . ?
C17 C12 C11 122.7(4) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.9(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(5) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.6(4) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 111.1 . . ?
N2 C19 H19B 111.1 . . ?
N2 C19 C20 103.4(3) . . ?
H19A C19 H19B 109.0 . . ?
C20 C19 H19A 111.1 . . ?
C20 C19 H19B 111.1 . . ?
C2 C20 C19 118.9(3) . . ?
C21 C20 C2 130.8(3) . . ?
C21 C20 C19 109.9(3) . . ?
C20 C21 C22 109.1(3) . . ?
C20 C21 C23 129.7(3) . . ?
C23 C21 C22 121.1(3) . . ?
N2 C22 C21 103.4(3) . . ?
N2 C22 H22A 111.1 . . ?
N2 C22 H22B 111.1 . . ?
C21 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.0 . . ?
C24 C23 C21 122.6(3) . . ?
C28 C23 C21 120.6(3) . . ?
C28 C23 C24 116.8(3) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.1(3) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 119.1 . . ?
C24 C25 C26 121.8(4) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 C36 121.3(4) . . ?
C27 C26 C25 117.4(4) . . ?
C27 C26 C36 121.3(4) . . ?
C26 C27 H27 119.4 . . ?
C26 C27 C28 121.3(3) . . ?
C28 C27 H27 119.4 . . ?
C23 C28 C27 121.6(3) . . ?
C23 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
N2 C29 H29A 109.5 . . ?
N2 C29 H29B 109.5 . . ?
N2 C29 C30 110.7(3) . . ?
H29A C29 H29B 108.1 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C31 C30 C29 121.5(4) . . ?
C35 C30 C29 121.1(4) . . ?
C35 C30 C31 117.4(4) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 C30 121.5(4) . . ?
C32 C31 H31 119.3 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.4(5) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 119.9(5) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.1(5) . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 120.7(5) . . ?
C30 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C26 C36 H36A 109.5 . . ?
C26 C36 H36B 109.5 . . ?
C26 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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 C1 C2 C3 16.7(4) . . . . ?
N1 C1 C2 C20 -167.3(3) . . . . ?
N1 C11 C12 C13 159.9(4) . . . . ?
N1 C11 C12 C17 -21.4(6) . . . . ?
N2 C19 C20 C2 -169.6(3) . . . . ?
N2 C19 C20 C21 16.9(4) . . . . ?
N2 C29 C30 C31 100.6(4) . . . . ?
N2 C29 C30 C35 -77.9(4) . . . . ?
C1 N1 C4 C3 26.6(4) . . . . ?
C1 N1 C11 C12 -65.0(5) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C5 176.2(3) . . . . ?
C1 C2 C20 C19 -100.4(3) . . . . ?
C1 C2 C20 C21 71.6(6) . . . . ?
C2 C3 C4 N1 -16.3(4) . . . . ?
C2 C3 C5 C6 -170.0(4) . . . . ?
C2 C3 C5 C10 9.7(6) . . . . ?
C2 C20 C21 C22 -172.9(4) . . . . ?
C2 C20 C21 C23 4.8(7) . . . . ?
C3 C2 C20 C19 74.7(5) . . . . ?
C3 C2 C20 C21 -113.3(4) . . . . ?
C3 C5 C6 C7 178.4(3) . . . . ?
C3 C5 C10 C9 -177.9(4) . . . . ?
C4 N1 C1 C2 -26.5(4) . . . . ?
C4 N1 C11 C12 172.9(3) . . . . ?
C4 C3 C5 C6 6.1(5) . . . . ?
C4 C3 C5 C10 -174.2(3) . . . . ?
C5 C3 C4 N1 166.8(3) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C6 C5 C10 C9 1.9(6) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C6 C7 C8 C18 -178.1(4) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C8 C9 C10 C5 -1.2(6) . . . . ?
C10 C5 C6 C7 -1.3(6) . . . . ?
C11 N1 C1 C2 -152.1(3) . . . . ?
C11 N1 C4 C3 153.3(3) . . . . ?
C11 C12 C13 C14 178.9(4) . . . . ?
C11 C12 C17 C16 179.4(4) . . . . ?
C12 C13 C14 C15 1.3(7) . . . . ?
C13 C12 C17 C16 -1.9(6) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
C15 C16 C17 C12 2.2(6) . . . . ?
C17 C12 C13 C14 0.2(6) . . . . ?
C18 C8 C9 C10 178.7(4) . . . . ?
C19 N2 C22 C21 26.4(4) . . . . ?
C19 N2 C29 C30 -64.1(4) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C19 C20 C21 C23 177.3(3) . . . . ?
C20 C2 C3 C4 -175.8(3) . . . . ?
C20 C2 C3 C5 0.7(6) . . . . ?
C20 C21 C22 N2 -16.1(4) . . . . ?
C20 C21 C23 C24 7.7(6) . . . . ?
C20 C21 C23 C28 -171.9(4) . . . . ?
C21 C23 C24 C25 -177.5(4) . . . . ?
C21 C23 C28 C27 177.7(4) . . . . ?
C22 N2 C19 C20 -26.6(4) . . . . ?
C22 N2 C29 C30 172.8(3) . . . . ?
C22 C21 C23 C24 -174.8(3) . . . . ?
C22 C21 C23 C28 5.7(5) . . . . ?
C23 C21 C22 N2 165.9(3) . . . . ?
C23 C24 C25 C26 -0.8(7) . . . . ?
C24 C23 C28 C27 -1.9(6) . . . . ?
C24 C25 C26 C27 -0.8(6) . . . . ?
C24 C25 C26 C36 179.2(4) . . . . ?
C25 C26 C27 C28 1.0(6) . . . . ?
C26 C27 C28 C23 0.4(6) . . . . ?
C28 C23 C24 C25 2.1(6) . . . . ?
C29 N2 C19 C20 -153.6(3) . . . . ?
C29 N2 C22 C21 153.8(3) . . . . ?
C29 C30 C31 C32 -178.6(4) . . . . ?
C29 C30 C35 C34 179.4(4) . . . . ?
C30 C31 C32 C33 -0.5(7) . . . . ?
C31 C30 C35 C34 0.9(6) . . . . ?
C31 C32 C33 C34 0.2(8) . . . . ?
C32 C33 C34 C35 0.7(8) . . . . ?
C33 C34 C35 C30 -1.2(7) . . . . ?
C35 C30 C31 C32 0.0(6) . . . . ?
C36 C26 C27 C28 -179.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.104
_oxdiff_exptl_absorpt_empirical_full_min 0.911
####################################################################### 
# 
# 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_t4461
_database_code_depnum_ccdc_archive 'CCDC 2395119'
loop_
_audit_author_name
_audit_author_address
'Guangwu Zhang'
;Henan University
China
;
_audit_update_record             
;
2024-10-31 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_audit_creation_date             2024-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C46 H36 N2'
_chemical_formula_sum            'C46 H36 N2'
_chemical_formula_weight         616.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H22O5N1
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   16.6526(4)
_cell_length_b                   5.85340(10)
_cell_length_c                   18.1057(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.461(3)
_cell_angle_gamma                90
_cell_volume                     1664.01(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4074
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1840
_cell_measurement_theta_min      4.3970
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10833
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.416
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -36.00   0.60    2.00    --  -33.50 178.00 -30.00  120
  2  ω    -92.00 -50.00   0.60    2.00    --  -33.50 178.00-120.00   70
  3  ω    -98.00 -15.80   0.60    2.00    --  -33.50 -57.00  60.00  137
  4  ω    -65.00 -20.60   0.60    2.00    --  -33.50 -57.00 -30.00   74
  5  ω    -46.00  -7.60   0.60    2.00    --  -33.50  19.00 120.00   64
  6  ω     37.00  63.40   0.60    2.00    --   36.47  19.00 -30.00   44
  7  ω      2.00  66.80   0.60    2.00    --   36.47 -99.00-180.00  108
  8  ω     61.00  86.20   0.60    2.00    --   36.47 178.00 -90.00   42
  9  ω     61.00 103.60   0.60    2.00    --   36.47 178.00-120.00   71
 10  ω     19.00  70.60   0.60    2.00    --   36.47  57.00 -60.00   86
 11  ω     18.00  77.40   0.60    2.00    --   36.47  57.00 -30.00   99
 12  ω    -17.00  49.00   0.60    2.00    --   36.47 -77.00 -90.00  110
 13  ω    -18.00  30.00   0.60    2.00    --   36.47 -77.00-120.00   80
 14  ω     66.00 107.40   0.60    2.00    --   36.47 178.00  90.00   69
 15  ω      3.00  32.40   0.60    2.00    --   36.47  19.00 -30.00   49
 16  ω     38.00  74.60   0.60    2.00    --   36.47 -99.00 -90.00   61
 17  ω     26.00  52.40   0.60    2.00    --   36.47 -99.00-150.00   44
 18  ω     44.80 109.00   0.60   14.00    --  108.00-111.00-180.00  107
 19  ω     39.00  72.60   0.60   14.00    --  108.00 -94.00-150.00   56
 20  ω    119.00 167.60   0.60   14.00    --  108.00  77.00 -60.00   81
 21  ω     43.00 178.00   0.60   14.00    --  108.00   0.00 -60.00  225
 22  ω    107.00 136.40   0.60   14.00    --  108.00 111.00  90.00   49
 23  ω     66.00 101.40   0.60   14.00    --  108.00 -95.00  75.00   59
 24  ω     47.00 101.00   0.60   14.00    --  108.00 -94.00-120.00   90
 25  ω    134.00 173.60   0.60   14.00    --  108.00  61.00   0.00   66
 26  ω     82.00 176.20   0.60   14.00    --  108.00  30.00 150.00  157
 27  ω     48.00  90.60   0.60   14.00    --  108.00 -94.00  30.00   71
 28  ω     76.60 109.00   0.60   14.00    --  108.00-111.00 -30.00   54
 29  ω    115.00 163.00   0.60   14.00    --  108.00 111.00-120.00   80
 30  ω    106.00 132.40   0.60   14.00    --  108.00 111.00-150.00   44
 31  ω     95.00 169.40   0.60   14.00    --  108.00  61.00 -30.00  124
 32  ω     41.00 118.40   0.60   14.00    --  108.00 -45.00 -30.00  129
 33  ω    141.00 176.40   0.60   14.00    --  108.00  77.00 120.00   59
 34  ω    147.00 173.40   0.60   14.00    --  108.00  61.00 -90.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0447132000
_diffrn_orient_matrix_UB_12      -0.1661743000
_diffrn_orient_matrix_UB_13      0.0396872000
_diffrn_orient_matrix_UB_21      -0.0680404000
_diffrn_orient_matrix_UB_22      0.1825785000
_diffrn_orient_matrix_UB_23      -0.0043417000
_diffrn_orient_matrix_UB_31      -0.0547159000
_diffrn_orient_matrix_UB_32      -0.0911769000
_diffrn_orient_matrix_UB_33      -0.0809616000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2455
_reflns_number_total             2950
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.105
_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)+(0.1115P)²+0.4206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22A) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq,
Uanis(C19A) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C23A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
Uanis(C23) = Uanis(C23A)
Uanis(C22) = Uanis(C22A)
Uanis(C21) = Uanis(C21A)
Uanis(C18) = Uanis(C18A)
3. Others
 Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=1-FVAR(1)
 Sof(C23)=Sof(H23)=Sof(C22)=Sof(H22)=Sof(C21)=Sof(H21)=Sof(C20)=Sof(H20)=
 Sof(C19)=Sof(H19)=Sof(C18)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A),
 C23(H23), C22(H22), C21(H21), C20(H20), C19(H19), C23A(H23A)
4.c Fitted hexagon refined as free rotating group:
 C23(C22,C21,C20,C19,C18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.39030(10) 0.8820(3) 0.41897(10) 0.0474(4) Uani 1 1 d . . . . .
C1 C 0.37518(13) 0.8732(3) 0.48803(12) 0.0482(5) Uani 1 1 d . . . . .
H1 H 0.3391 0.9705 0.5028 0.058 Uiso 1 1 calc R . . . .
C2 C 0.42156(12) 0.6979(3) 0.53264(11) 0.0430(4) Uani 1 1 d . . . . .
C3 C 0.46940(11) 0.5955(3) 0.48840(10) 0.0407(4) Uani 1 1 d . . . . .
C4 C 0.44791(12) 0.7156(3) 0.41926(11) 0.0446(5) Uani 1 1 d . . . . .
H4 H 0.4694 0.6878 0.3788 0.053 Uiso 1 1 calc R . . . .
C5 C 0.41389(12) 0.6413(3) 0.60993(11) 0.0445(5) Uani 1 1 d . . . . .
C6 C 0.43304(14) 0.8049(4) 0.66881(12) 0.0528(5) Uani 1 1 d . . . . .
H6 H 0.4556 0.9445 0.6609 0.063 Uiso 1 1 calc R . . . .
C7 C 0.41937(14) 0.7651(4) 0.73904(12) 0.0562(5) Uani 1 1 d . . . . .
H7 H 0.4329 0.8788 0.7771 0.067 Uiso 1 1 calc R . . . .
C8 C 0.38615(13) 0.5605(4) 0.75414(12) 0.0525(5) Uani 1 1 d . . . . .
C9 C 0.36690(16) 0.3973(4) 0.69507(13) 0.0581(6) Uani 1 1 d . . . . .
H9 H 0.3442 0.2580 0.7030 0.070 Uiso 1 1 calc R . . . .
C10 C 0.38056(15) 0.4364(4) 0.62493(13) 0.0550(5) Uani 1 1 d . . . . .
H10 H 0.3671 0.3226 0.5869 0.066 Uiso 1 1 calc R . . . .
C11 C 0.35986(14) 1.0602(4) 0.35929(13) 0.0554(5) Uani 1 1 d . . . . .
H11A H 0.3624 1.0038 0.3097 0.066 Uiso 1 1 calc R . . . .
H11B H 0.3971 1.1920 0.3742 0.066 Uiso 1 1 calc R . . . .
C12 C 0.26954(12) 1.1322(3) 0.34911(11) 0.0452(5) Uani 1 1 d . . . . .
C13 C 0.25365(15) 1.3376(4) 0.37906(14) 0.0589(6) Uani 1 1 d . . . . .
H13 H 0.2985 1.4335 0.4057 0.071 Uiso 1 1 calc R . . . .
C14 C 0.1698(2) 1.4005(5) 0.36905(18) 0.0772(8) Uani 1 1 d . . . . .
H14 H 0.1586 1.5393 0.3887 0.093 Uiso 1 1 calc R . . . .
C15 C 0.10380(16) 1.2581(6) 0.33030(18) 0.0801(9) Uani 1 1 d . . . . .
H15 H 0.0480 1.2993 0.3243 0.096 Uiso 1 1 calc R . . . .
C16 C 0.11998(16) 1.0563(6) 0.30066(16) 0.0771(8) Uani 1 1 d . . . . .
H16 H 0.0751 0.9610 0.2738 0.092 Uiso 1 1 calc R . . . .
C17 C 0.20179(15) 0.9930(4) 0.31020(13) 0.0607(6) Uani 1 1 d . . . . .
H17 H 0.2120 0.8538 0.2902 0.073 Uiso 1 1 calc R . . . .
C18A C 0.3629(7) 0.5172(19) 0.8253(4) 0.0585(9) Uani 0.412(3) 1 d . . P A 2
C19A C 0.3598(6) 0.6921(17) 0.8764(4) 0.0928(14) Uani 0.412(3) 1 d . U P A 2
H19A H 0.3680 0.8409 0.8623 0.111 Uiso 0.412(3) 1 calc R . P A 2
C20A C 0.3456(7) 0.660(2) 0.9462(5) 0.1109(18) Uani 0.412(3) 1 d . U P A 2
H20A H 0.3480 0.7830 0.9796 0.133 Uiso 0.412(3) 1 calc R . P A 2
C21A C 0.3278(9) 0.443(2) 0.9659(6) 0.0965(19) Uani 0.412(3) 1 d . U P A 2
H21A H 0.3142 0.4189 1.0111 0.116 Uiso 0.412(3) 1 calc R . P A 2
C22A C 0.3302(6) 0.2674(19) 0.9199(6) 0.0836(17) Uani 0.412(3) 1 d . U P A 2
H22A H 0.3223 0.1196 0.9350 0.100 Uiso 0.412(3) 1 calc R . P A 2
C23 C 0.3136(3) 0.3820(9) 0.8379(2) 0.0687(13) Uani 0.588(3) 1 d . U P A 1
H23 H 0.2783 0.3091 0.7933 0.082 Uiso 0.588(3) 1 calc R . P A 1
C22 C 0.3015(3) 0.3489(9) 0.9095(3) 0.0836(17) Uani 0.588(3) 1 d G U P A 1
H22 H 0.2581 0.2538 0.9127 0.100 Uiso 0.588(3) 1 calc R . P A 1
C21 C 0.3543(3) 0.4579(11) 0.9762(2) 0.0965(19) Uani 0.588(3) 1 d G U P A 1
H21 H 0.3462 0.4357 1.0241 0.116 Uiso 0.588(3) 1 calc R . P A 1
C20 C 0.4192(3) 0.6000(9) 0.97140(19) 0.1109(18) Uani 0.588(3) 1 d G U P A 1
H20 H 0.4545 0.6730 1.0160 0.133 Uiso 0.588(3) 1 calc R . P A 1
C19 C 0.4313(3) 0.6332(9) 0.8998(2) 0.0928(14) Uani 0.588(3) 1 d G U P A 1
H19 H 0.4748 0.7283 0.8966 0.111 Uiso 0.588(3) 1 calc R . P A 1
C18 C 0.3785(3) 0.5242(10) 0.83309(19) 0.0585(9) Uani 0.588(3) 1 d G . P A 1
C23A C 0.3445(5) 0.3031(15) 0.8493(5) 0.0687(13) Uani 0.412(3) 1 d . U P A 2
H23A H 0.3416 0.1784 0.8166 0.082 Uiso 0.412(3) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.356(3) . ?
N1 C4 1.366(2) . ?
N1 C11 1.465(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.373(3) . ?
C2 C3 1.436(3) . ?
C2 C5 1.484(3) . ?
C3 C3 1.476(4) 3_666 ?
C3 C4 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 C10 1.386(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(3) . ?
C8 C9 1.390(3) . ?
C8 C18A 1.485(7) . ?
C8 C18 1.492(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.513(3) . ?
C12 C13 1.380(3) . ?
C12 C17 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.397(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.366(4) . ?
C17 H17 0.9300 . ?
C18A C19A 1.393(13) . ?
C18A C23A 1.394(12) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.374(10) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.381(16) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.332(15) . ?
C22A H22A 0.9300 . ?
C22A C23A 1.391(10) . ?
C23 H23 0.9300 . ?
C23 C22 1.3900 . ?
C23 C18 1.3900 . ?
C22 H22 0.9300 . ?
C22 C21 1.3900 . ?
C21 H21 0.9300 . ?
C21 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C23A H23A 0.9300 . ?

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 N1 C4 108.36(16) . . ?
C1 N1 C11 125.61(17) . . ?
C4 N1 C11 125.47(17) . . ?
N1 C1 H1 125.4 . . ?
N1 C1 C2 109.28(17) . . ?
C2 C1 H1 125.4 . . ?
C1 C2 C3 106.96(17) . . ?
C1 C2 C5 120.88(17) . . ?
C3 C2 C5 132.13(17) . . ?
C2 C3 C3 128.1(2) . 3_666 ?
C4 C3 C2 105.66(16) . . ?
C4 C3 C3 126.3(2) . 3_666 ?
N1 C4 C3 109.73(16) . . ?
N1 C4 H4 125.1 . . ?
C3 C4 H4 125.1 . . ?
C6 C5 C2 119.98(18) . . ?
C10 C5 C2 122.94(18) . . ?
C10 C5 C6 116.81(18) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 116.60(19) . . ?
C7 C8 C18A 123.8(4) . . ?
C7 C8 C18 118.7(3) . . ?
C9 C8 C18A 119.3(4) . . ?
C9 C8 C18 124.6(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 H9 119.1 . . ?
C5 C10 H10 119.2 . . ?
C9 C10 C5 121.5(2) . . ?
C9 C10 H10 119.2 . . ?
N1 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
N1 C11 C12 111.95(17) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C13 C12 C11 120.5(2) . . ?
C17 C12 C11 120.5(2) . . ?
C17 C12 C13 118.9(2) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C19A C18A C8 121.9(8) . . ?
C19A C18A C23A 113.2(6) . . ?
C23A C18A C8 124.9(8) . . ?
C18A C19A H19A 117.7 . . ?
C20A C19A C18A 124.6(9) . . ?
C20A C19A H19A 117.7 . . ?
C19A C20A H20A 120.7 . . ?
C19A C20A C21A 118.6(10) . . ?
C21A C20A H20A 120.7 . . ?
C20A C21A H21A 120.1 . . ?
C22A C21A C20A 119.7(8) . . ?
C22A C21A H21A 120.1 . . ?
C21A C22A H22A 119.7 . . ?
C21A C22A C23A 120.6(9) . . ?
C23A C22A H22A 119.7 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C18 120.0 . . ?
C18 C23 H23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C23 C18 C8 117.5(3) . . ?
C19 C18 C8 122.4(3) . . ?
C19 C18 C23 120.0 . . ?
C18A C23A H23A 118.5 . . ?
C22A C23A C18A 122.9(8) . . ?
C22A C23A H23A 118.5 . . ?

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 C1 C2 C3 1.1(2) . . . . ?
N1 C1 C2 C5 -176.90(17) . . . . ?
N1 C11 C12 C13 104.9(2) . . . . ?
N1 C11 C12 C17 -74.7(3) . . . . ?
C1 N1 C4 C3 0.9(2) . . . . ?
C1 N1 C11 C12 -40.1(3) . . . . ?
C1 C2 C3 C3 178.3(2) . . . 3_666 ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C5 C6 -59.3(3) . . . . ?
C1 C2 C5 C10 114.5(2) . . . . ?
C2 C3 C4 N1 -0.3(2) . . . . ?
C2 C5 C6 C7 174.12(19) . . . . ?
C2 C5 C10 C9 -173.9(2) . . . . ?
C3 C2 C5 C6 123.3(2) . . . . ?
C3 C2 C5 C10 -62.9(3) . . . . ?
C3 C3 C4 N1 -179.1(2) 3_666 . . . ?
C4 N1 C1 C2 -1.3(2) . . . . ?
C4 N1 C11 C12 149.5(2) . . . . ?
C5 C2 C3 C3 -4.0(4) . . . 3_666 ?
C5 C2 C3 C4 177.2(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C6 C7 C8 C18A -174.1(6) . . . . ?
C6 C7 C8 C18 176.0(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C18A C19A 10.6(13) . . . . ?
C7 C8 C18A C23A -167.5(7) . . . . ?
C7 C8 C18 C23 150.8(3) . . . . ?
C7 C8 C18 C19 -26.7(5) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C8 C18A C19A C20A -174.4(8) . . . . ?
C8 C18A C23A C22A 174.2(7) . . . . ?
C9 C8 C18A C19A -163.1(8) . . . . ?
C9 C8 C18A C23A 18.8(13) . . . . ?
C9 C8 C18 C23 -33.3(5) . . . . ?
C9 C8 C18 C19 149.2(3) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C11 N1 C1 C2 -173.07(19) . . . . ?
C11 N1 C4 C3 172.76(19) . . . . ?
C11 C12 C13 C14 -179.9(2) . . . . ?
C11 C12 C17 C16 180.0(2) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C17 C12 C13 C14 -0.4(3) . . . . ?
C18A C8 C9 C10 174.5(5) . . . . ?
C18A C19A C20A C21A -4.2(18) . . . . ?
C19A C18A C23A C22A -4.0(15) . . . . ?
C19A C20A C21A C22A 4(2) . . . . ?
C20A C21A C22A C23A -4.7(19) . . . . ?
C21A C22A C23A C18A 4.7(15) . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C22 C23 C18 C8 -177.6(5) . . . . ?
C22 C23 C18 C19 0.0 . . . . ?
C22 C21 C20 C19 0.0 . . . . ?
C21 C20 C19 C18 0.0 . . . . ?
C20 C19 C18 C8 177.4(6) . . . . ?
C20 C19 C18 C23 0.0 . . . . ?
C18 C8 C9 C10 -175.7(3) . . . . ?
C18 C23 C22 C21 0.0 . . . . ?
C23A C18A C19A C20A 3.9(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.870
_oxdiff_exptl_absorpt_empirical_full_min 0.864
####################################################################### 
# 
# 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_202412t496f1_auto
_database_code_depnum_ccdc_archive 'CCDC 2413453'
loop_
_audit_author_name
_audit_author_address
'Guangwu Zhang'
;Henan University
China
;
_audit_update_record             
;
2024-12-28 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_audit_creation_date             2024-12-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H32 N2 O2'
_chemical_formula_sum            'C38 H32 N2 O2'
_chemical_formula_weight         548.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOCl
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   26.2762(11)
_cell_length_b                   10.1154(3)
_cell_length_c                   12.3299(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.268(5)
_cell_angle_gamma                90
_cell_volume                     2938.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7091
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.7170
_cell_measurement_theta_min      1.7520
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11065
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.940
_diffrn_reflns_theta_min         1.728
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -53.00   0.50    0.80    --  -20.24 127.00-104.00   50
  2  ω    -89.00 -64.00   0.50    0.80    --  -20.24 145.00  63.00   50
  3  ω    -42.00  62.00   0.50    0.80    --  -20.24  38.00 120.00  208
  4  ω    -25.00  55.00   0.50    0.80    --  -20.24  19.00  30.00  160
  5  ω    -21.00  17.00   0.50    0.80    --   22.51  19.00 -30.00   76
  6  ω     49.00  74.00   0.50    0.80    --   22.51-145.00  10.00   50
  7  ω     32.00  95.00   0.50    0.80    --   22.51-127.00 179.00  126
  8  ω     61.00  87.00   0.50    0.80    --   22.51  19.00 -30.00   52
  9  ω     46.00 105.00   0.50    0.80    --   22.51 178.00  90.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0136254865
_diffrn_orient_matrix_UB_12      -0.0559456841
_diffrn_orient_matrix_UB_13      -0.0357560808
_diffrn_orient_matrix_UB_21      0.0200945938
_diffrn_orient_matrix_UB_22      -0.0420017530
_diffrn_orient_matrix_UB_23      0.0443943596
_diffrn_orient_matrix_UB_31      -0.0178120638
_diffrn_orient_matrix_UB_32      -0.0046181813
_diffrn_orient_matrix_UB_33      0.0294218329
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2812
_reflns_number_total             3418
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.081
_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)+(0.0418P)²+1.3865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          ?
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.c 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
O1 O 0.64588(4) 0.72950(10) 0.71248(8) 0.0347(2) Uani 1 1 d . . . . .
N1 N 0.61159(4) 0.78682(9) 0.46457(8) 0.0205(2) Uani 1 1 d . . . . .
C1 C 0.55401(6) 0.74424(17) 0.70046(12) 0.0401(4) Uani 1 1 d . . . . .
H1A H 0.573705 0.717242 0.785447 0.060 Uiso 1 1 calc R U . . .
H1B H 0.523324 0.681654 0.655930 0.060 Uiso 1 1 calc R U . . .
H1C H 0.538087 0.832943 0.695257 0.060 Uiso 1 1 calc R U . . .
C2 C 0.59538(5) 0.74559(11) 0.64625(10) 0.0231(2) Uani 1 1 d . . . . .
C3 C 0.57456(4) 0.76696(11) 0.51616(10) 0.0197(2) Uani 1 1 d . . . . .
C4 C 0.51937(5) 0.76984(11) 0.42188(10) 0.0198(2) Uani 1 1 d . . . . .
C5 C 0.52334(4) 0.78982(11) 0.31165(10) 0.0211(2) Uani 1 1 d . . . . .
C6 C 0.58098(5) 0.80170(12) 0.34371(10) 0.0225(2) Uani 1 1 d . . . . .
H6 H 0.596601 0.817921 0.288660 0.027 Uiso 1 1 calc R U . . .
C7 C 0.46503(4) 0.75399(11) 0.43102(10) 0.0200(2) Uani 1 1 d . . . . .
C8 C 0.43896(5) 0.86189(12) 0.45565(11) 0.0258(3) Uani 1 1 d . . . . .
H8 H 0.456631 0.946231 0.469389 0.031 Uiso 1 1 calc R U . . .
C9 C 0.38744(5) 0.84767(13) 0.46038(11) 0.0306(3) Uani 1 1 d . . . . .
H9 H 0.370208 0.922049 0.477715 0.037 Uiso 1 1 calc R U . . .
C10 C 0.36120(5) 0.72595(14) 0.44000(12) 0.0335(3) Uani 1 1 d . . . . .
H10 H 0.325939 0.716395 0.443284 0.040 Uiso 1 1 calc R U . . .
C11 C 0.38635(6) 0.61785(14) 0.41476(13) 0.0354(3) Uani 1 1 d . . . . .
H11 H 0.368265 0.533976 0.400334 0.042 Uiso 1 1 calc R U . . .
C12 C 0.43813(5) 0.63167(12) 0.41045(11) 0.0281(3) Uani 1 1 d . . . . .
H12 H 0.455252 0.556947 0.393326 0.034 Uiso 1 1 calc R U . . .
C13 C 0.67405(4) 0.79386(11) 0.52375(10) 0.0213(2) Uani 1 1 d . . . . .
H13A H 0.686513 0.835238 0.604258 0.026 Uiso 1 1 calc R U . . .
H13B H 0.686313 0.852212 0.475269 0.026 Uiso 1 1 calc R U . . .
C14 C 0.70365(4) 0.66205(11) 0.53981(10) 0.0202(2) Uani 1 1 d . . . . .
C15 C 0.74651(5) 0.62714(12) 0.65275(10) 0.0249(3) Uani 1 1 d . . . . .
H15 H 0.754607 0.682624 0.720592 0.030 Uiso 1 1 calc R U . . .
C16 C 0.77748(5) 0.51162(13) 0.66671(11) 0.0290(3) Uani 1 1 d . . . . .
H16 H 0.806741 0.488911 0.743932 0.035 Uiso 1 1 calc R U . . .
C17 C 0.76595(5) 0.42947(12) 0.56875(12) 0.0295(3) Uani 1 1 d . . . . .
H17 H 0.787155 0.350556 0.578609 0.035 Uiso 1 1 calc R U . . .
C18 C 0.72319(5) 0.46312(12) 0.45599(12) 0.0292(3) Uani 1 1 d . . . . .
H18 H 0.715008 0.407054 0.388478 0.035 Uiso 1 1 calc R U . . .
C19 C 0.69239(5) 0.57868(12) 0.44193(10) 0.0249(2) Uani 1 1 d . . . . .
H19 H 0.663245 0.601190 0.364500 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2227(14) . ?
N1 C3 1.3928(13) . ?
N1 C6 1.3525(14) . ?
N1 C13 1.4733(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5073(16) . ?
C2 C3 1.4636(16) . ?
C3 C4 1.4010(15) . ?
C4 C5 1.4228(15) . ?
C4 C7 1.4898(14) . ?
C5 C5 1.472(2) 2_655 ?
C5 C6 1.3909(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3918(16) . ?
C7 C12 1.3914(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3880(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3790(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3919(17) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5119(16) . ?
C14 C15 1.3944(15) . ?
C14 C19 1.3925(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3905(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3846(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3887(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3883(17) . ?
C19 H19 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
C3 N1 C13 129.13(9) . . ?
C6 N1 C3 108.93(9) . . ?
C6 N1 C13 121.94(9) . . ?
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 . . ?
O1 C2 C1 119.02(11) . . ?
O1 C2 C3 121.36(10) . . ?
C3 C2 C1 119.61(10) . . ?
N1 C3 C2 121.60(10) . . ?
N1 C3 C4 107.09(9) . . ?
C4 C3 C2 131.31(10) . . ?
C3 C4 C5 108.00(9) . . ?
C3 C4 C7 127.56(10) . . ?
C5 C4 C7 124.43(10) . . ?
C4 C5 C5 127.36(12) . 2_655 ?
C6 C5 C4 105.77(9) . . ?
C6 C5 C5 126.77(12) . 2_655 ?
N1 C6 C5 110.19(10) . . ?
N1 C6 H6 124.9 . . ?
C5 C6 H6 124.9 . . ?
C8 C7 C4 120.85(10) . . ?
C12 C7 C4 120.57(10) . . ?
C12 C7 C8 118.53(10) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.75(11) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.22(11) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.79(11) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.13(12) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.58(11) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
N1 C13 H13A 108.6 . . ?
N1 C13 H13B 108.6 . . ?
N1 C13 C14 114.71(9) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C15 C14 C13 119.70(10) . . ?
C19 C14 C13 121.39(10) . . ?
C19 C14 C15 118.69(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.42(11) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.41(11) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.60(12) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.01(12) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.87(11) . . ?
C18 C19 H19 119.6 . . ?

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 C2 C3 N1 -8.38(17) . . . . ?
O1 C2 C3 C4 170.26(12) . . . . ?
N1 C3 C4 C5 0.85(12) . . . . ?
N1 C3 C4 C7 -179.68(10) . . . . ?
N1 C13 C14 C15 -129.85(10) . . . . ?
N1 C13 C14 C19 55.52(13) . . . . ?
C1 C2 C3 N1 171.18(11) . . . . ?
C1 C2 C3 C4 -10.18(19) . . . . ?
C2 C3 C4 C5 -177.93(11) . . . . ?
C2 C3 C4 C7 1.5(2) . . . . ?
C3 N1 C6 C5 -1.08(13) . . . . ?
C3 N1 C13 C14 87.74(13) . . . . ?
C3 C4 C5 C5 175.11(6) . . . 2_655 ?
C3 C4 C5 C6 -1.47(13) . . . . ?
C3 C4 C7 C8 85.89(15) . . . . ?
C3 C4 C7 C12 -96.60(14) . . . . ?
C4 C5 C6 N1 1.57(13) . . . . ?
C4 C7 C8 C9 177.97(11) . . . . ?
C4 C7 C12 C11 -177.71(11) . . . . ?
C5 C4 C7 C8 -94.73(14) . . . . ?
C5 C4 C7 C12 82.79(15) . . . . ?
C5 C5 C6 N1 -175.03(6) 2_655 . . . ?
C6 N1 C3 C2 179.05(10) . . . . ?
C6 N1 C3 C4 0.12(12) . . . . ?
C6 N1 C13 C14 -93.11(13) . . . . ?
C7 C4 C5 C5 -4.37(14) . . . 2_655 ?
C7 C4 C5 C6 179.04(10) . . . . ?
C7 C8 C9 C10 -0.34(19) . . . . ?
C8 C7 C12 C11 -0.14(18) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C12 C7 C8 C9 0.41(18) . . . . ?
C13 N1 C3 C2 -1.72(17) . . . . ?
C13 N1 C3 C4 179.36(10) . . . . ?
C13 N1 C6 C5 179.62(10) . . . . ?
C13 C14 C15 C16 -174.42(10) . . . . ?
C13 C14 C19 C18 174.56(10) . . . . ?
C14 C15 C16 C17 -0.33(17) . . . . ?
C15 C14 C19 C18 -0.13(16) . . . . ?
C15 C16 C17 C18 0.08(17) . . . . ?
C16 C17 C18 C19 0.15(17) . . . . ?
C17 C18 C19 C14 -0.13(17) . . . . ?
C19 C14 C15 C16 0.36(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.786
