# Supplementary Information (SI) for Chemical Science.
# 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_np-h-xin
_database_code_depnum_ccdc_archive 'CCDC 2352008'
loop_
_audit_author_name
_audit_author_address
'Weihan Guo'
;Nanchang University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2024-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 N2 O'
_chemical_formula_sum            'C25 H20 N2 O'
_chemical_formula_weight         364.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0247(4)
_cell_length_b                   10.5190(5)
_cell_length_c                   11.3139(5)
_cell_angle_alpha                111.372(4)
_cell_angle_beta                 115.622(4)
_cell_angle_gamma                95.402(4)
_cell_volume                     955.68(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6306
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.9470
_cell_measurement_theta_min      2.2350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.786
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11170
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.786
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.822
_diffrn_reflns_theta_min         2.179
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.786
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3194
_reflns_number_total             6008
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         6008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.012
_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)+(0.0940P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1596
_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:
 C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C19(H19), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7418(2) 0.77100(19) 0.8025(2) 0.0821(6) Uani 1 1 d . . . . .
H1 H 0.781360 0.855153 0.803389 0.099 Uiso 1 1 calc R . . . .
C2 C 0.7280(2) 0.77599(16) 0.91825(19) 0.0765(5) Uani 1 1 d . . . . .
H2 H 0.758839 0.863636 0.998674 0.092 Uiso 1 1 calc R . . . .
C3 C 0.66803(19) 0.65115(15) 0.91691(15) 0.0614(4) Uani 1 1 d . . . . .
H3 H 0.659209 0.654938 0.996563 0.074 Uiso 1 1 calc R . . . .
C4 C 0.62156(14) 0.52163(13) 0.79793(13) 0.0470(3) Uani 1 1 d . . . . .
C5 C 0.63749(17) 0.51752(16) 0.68214(14) 0.0597(4) Uani 1 1 d . . . . .
H5 H 0.607562 0.430300 0.601562 0.072 Uiso 1 1 calc R . . . .
C6 C 0.6979(2) 0.6429(2) 0.68545(18) 0.0787(5) Uani 1 1 d . . . . .
H6 H 0.708681 0.639709 0.606904 0.094 Uiso 1 1 calc R . . . .
C7 C 0.89189(17) 0.30817(15) 1.01827(15) 0.0614(4) Uani 1 1 d . . . . .
H7 H 0.999327 0.339252 1.062835 0.074 Uiso 1 1 calc R . . . .
C8 C 0.80333(15) 0.37067(14) 0.93720(14) 0.0520(3) Uani 1 1 d . . . . .
H8 H 0.851539 0.442081 0.926214 0.062 Uiso 1 1 calc R . . . .
C9 C 0.64267(14) 0.32778(12) 0.87185(12) 0.0435(3) Uani 1 1 d . . . . .
C10 C 0.57399(16) 0.21834(13) 0.88775(14) 0.0504(3) Uani 1 1 d . . . . .
H10 H 0.466669 0.186821 0.843932 0.060 Uiso 1 1 calc R . . . .
C11 C 0.66435(19) 0.15662(15) 0.96809(16) 0.0623(4) Uani 1 1 d . . . . .
H11 H 0.616901 0.083822 0.977965 0.075 Uiso 1 1 calc R . . . .
C12 C 0.82318(19) 0.20042(16) 1.03395(17) 0.0679(4) Uani 1 1 d . . . . .
H12 H 0.883110 0.158098 1.088078 0.081 Uiso 1 1 calc R . . . .
C13 C 0.38702(15) 0.34081(13) 0.71305(14) 0.0480(3) Uani 1 1 d . . . . .
C14 C 0.30357(18) 0.41761(16) 0.76241(15) 0.0582(4) Uani 1 1 d . . . . .
H14 H 0.358016 0.501040 0.850661 0.070 Uiso 1 1 calc R . . . .
C15 C 0.13912(18) 0.37824(17) 0.68766(16) 0.0612(4) Uani 1 1 d . . . . .
H15 H 0.087011 0.434519 0.724622 0.073 Uiso 1 1 calc R . . . .
C16 C 0.06113(15) 0.25543(15) 0.56033(14) 0.0505(3) Uani 1 1 d . . . . .
C17 C 0.14536(14) 0.17467(13) 0.50931(13) 0.0442(3) Uani 1 1 d . . . . .
C18 C 0.30621(13) 0.21097(12) 0.57906(13) 0.0437(3) Uani 1 1 d . . . . .
C19 C 0.36471(15) 0.11620(14) 0.50396(14) 0.0502(3) Uani 1 1 d . . . . .
H19 H 0.471365 0.134403 0.543717 0.060 Uiso 1 1 calc R . . . .
C20 C 0.26651(17) -0.00280(15) 0.37276(15) 0.0581(4) Uani 1 1 d . . . . .
H20 H 0.308969 -0.062936 0.325808 0.070 Uiso 1 1 calc R . . . .
C21 C 0.04441(15) 0.05414(14) 0.37622(14) 0.0492(3) Uani 1 1 d . . . . .
C22 C 0.10390(17) -0.03708(15) 0.30678(15) 0.0581(4) Uani 1 1 d . . . . .
H22 H 0.039409 -0.119103 0.218885 0.070 Uiso 1 1 calc R . . . .
C23 C -0.11430(15) 0.06159(17) 0.34127(16) 0.0574(4) Uani 1 1 d . . . . .
C24 C -0.22522(19) 0.2348(2) 0.4584(2) 0.0749(5) Uani 1 1 d . . . . .
H24A H -0.202130 0.284573 0.559130 0.090 Uiso 1 1 calc R . . . .
H24B H -0.317091 0.153574 0.406228 0.090 Uiso 1 1 calc R . . . .
C25 C -0.2579(3) 0.3334(3) 0.3890(3) 0.1067(8) Uani 1 1 d . . . . .
H25A H -0.266338 0.289661 0.294325 0.160 Uiso 1 1 calc GR . . . .
H25B H -0.174986 0.421696 0.450268 0.160 Uiso 1 1 calc GR . . . .
H25C H -0.353500 0.352123 0.377839 0.160 Uiso 1 1 calc GR . . . .
N1 N -0.09625(13) 0.18364(14) 0.45704(13) 0.0590(3) Uani 1 1 d . . . . .
N2 N 0.55271(12) 0.39132(11) 0.79090(12) 0.0541(3) Uani 1 1 d . . . . .
O1 O -0.23865(12) -0.01765(14) 0.23377(12) 0.0816(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.358(3) . ?
C1 C6 1.359(3) . ?
C2 C3 1.384(2) . ?
C3 C4 1.3736(19) . ?
C4 C5 1.3728(19) . ?
C4 N2 1.4341(14) . ?
C5 C6 1.378(2) . ?
C7 C8 1.3809(19) . ?
C7 C12 1.377(2) . ?
C8 C9 1.3908(17) . ?
C9 C10 1.3930(16) . ?
C9 N2 1.3942(15) . ?
C10 C11 1.377(2) . ?
C11 C12 1.374(2) . ?
C13 C14 1.366(2) . ?
C13 C18 1.4284(18) . ?
C13 N2 1.4298(16) . ?
C14 C15 1.419(2) . ?
C15 C16 1.355(2) . ?
C16 C17 1.403(2) . ?
C16 N1 1.4010(17) . ?
C17 C18 1.3901(16) . ?
C17 C21 1.3957(17) . ?
C18 C19 1.408(2) . ?
C19 C20 1.3745(19) . ?
C20 C22 1.409(2) . ?
C21 C22 1.363(2) . ?
C21 C23 1.482(2) . ?
C23 N1 1.386(2) . ?
C23 O1 1.2175(16) . ?
C24 C25 1.495(3) . ?
C24 N1 1.450(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
C2 C1 C6 119.92(13) . . ?
C1 C2 C3 120.24(15) . . ?
C4 C3 C2 120.00(14) . . ?
C3 C4 N2 121.11(11) . . ?
C5 C4 C3 119.34(12) . . ?
C5 C4 N2 119.53(12) . . ?
C4 C5 C6 119.91(14) . . ?
C1 C6 C5 120.58(14) . . ?
C12 C7 C8 120.85(13) . . ?
C7 C8 C9 120.58(11) . . ?
C8 C9 C10 118.22(11) . . ?
C8 C9 N2 120.85(10) . . ?
C10 C9 N2 120.93(11) . . ?
C11 C10 C9 120.28(13) . . ?
C12 C11 C10 121.35(12) . . ?
C11 C12 C7 118.72(13) . . ?
C14 C13 C18 119.02(13) . . ?
C14 C13 N2 120.89(12) . . ?
C18 C13 N2 120.06(12) . . ?
C13 C14 C15 124.22(14) . . ?
C16 C15 C14 117.33(14) . . ?
C15 C16 C17 119.04(12) . . ?
C15 C16 N1 134.10(13) . . ?
N1 C16 C17 106.86(12) . . ?
C18 C17 C16 125.03(12) . . ?
C18 C17 C21 124.75(12) . . ?
C21 C17 C16 110.20(12) . . ?
C17 C18 C13 115.36(12) . . ?
C17 C18 C19 114.82(11) . . ?
C19 C18 C13 129.78(12) . . ?
C20 C19 C18 120.98(12) . . ?
C19 C20 C22 122.44(14) . . ?
C17 C21 C23 106.14(12) . . ?
C22 C21 C17 119.30(12) . . ?
C22 C21 C23 134.52(13) . . ?
C21 C22 C20 117.69(13) . . ?
N1 C23 C21 105.98(11) . . ?
O1 C23 C21 129.52(17) . . ?
O1 C23 N1 124.49(16) . . ?
N1 C24 C25 112.35(14) . . ?
C16 N1 C24 125.98(15) . . ?
C23 N1 C16 110.80(12) . . ?
C23 N1 C24 122.86(13) . . ?
C9 N2 C4 121.22(10) . . ?
C9 N2 C13 121.61(9) . . ?
C13 N2 C4 116.67(10) . . ?

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

data_np-me-0
_database_code_depnum_ccdc_archive 'CCDC 2352011'
loop_
_audit_author_name
_audit_author_address
'Weihan Guo'
;Nanchang University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-11-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.093(C27 H24 N2 O)'
_chemical_formula_sum            'C27 H24 N2 O'
_chemical_formula_weight         392.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9874(5)
_cell_length_b                   17.6677(9)
_cell_length_c                   10.4520(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.409(2)
_cell_angle_gamma                90
_cell_volume                     2134.05(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8562
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0761 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.4058.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            40042
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.415
_diffrn_reflns_theta_min         2.106
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3440
_reflns_number_total             4341
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.086
_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)+(0.1035P)²+0.5446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1776
_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:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C18(H18), C11(H11), C26(H26), C15(H15), C23(H23),
 C16(H16), C13(H13), C12(H12), C25(H25), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_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 0.06287(13) 0.36775(10) 0.42637(16) 0.0533(4) Uani 1 1 d . . . . .
N1 N 0.13586(13) 0.31274(10) 0.26454(17) 0.0372(4) Uani 1 1 d . . . . .
N2 N 0.60235(14) 0.31061(9) 0.25824(18) 0.0403(4) Uani 1 1 d . . . . .
C10 C 0.44276(15) 0.34919(10) 0.35362(19) 0.0327(4) Uani 1 1 d . . . . .
C19 C 0.73407(16) 0.22160(11) 0.19188(19) 0.0358(4) Uani 1 1 d . . . . .
H19 H 0.747654 0.257367 0.129830 0.043 Uiso 1 1 calc R U . . .
C14 C 0.65933(16) 0.23947(11) 0.26894(19) 0.0335(4) Uani 1 1 d . . . . .
C5 C 0.32416(16) 0.34522(10) 0.34041(18) 0.0317(4) Uani 1 1 d . . . . .
C22 C 0.58589(17) 0.43827(12) 0.16824(19) 0.0378(4) Uani 1 1 d . . . . .
H22 H 0.504223 0.432602 0.139286 0.045 Uiso 1 1 calc R U . . .
C4 C 0.26790(17) 0.37752(11) 0.42788(19) 0.0350(4) Uani 1 1 d . . . . .
C18 C 0.78890(16) 0.15172(12) 0.2053(2) 0.0380(5) Uani 1 1 d . . . . .
H18 H 0.840642 0.140655 0.152942 0.046 Uiso 1 1 calc R U . . .
C9 C 0.48170(16) 0.31057(11) 0.2532(2) 0.0360(4) Uani 1 1 d . . . . .
C11 C 0.50701(17) 0.38867(11) 0.46663(19) 0.0362(4) Uani 1 1 d . . . . .
H11 H 0.588561 0.393127 0.482870 0.043 Uiso 1 1 calc R U . . .
C3 C 0.14327(17) 0.35524(12) 0.3787(2) 0.0382(5) Uani 1 1 d . . . . .
C21 C 0.65373(17) 0.37887(11) 0.2337(2) 0.0351(4) Uani 1 1 d . . . . .
C6 C 0.24447(16) 0.30579(10) 0.23957(19) 0.0339(4) Uani 1 1 d . . . . .
C26 C 0.77327(18) 0.39008(12) 0.2784(2) 0.0427(5) Uani 1 1 d . . . . .
H26 H 0.821183 0.351168 0.326590 0.051 Uiso 1 1 calc R U . . .
C15 C 0.63852(17) 0.18531(12) 0.35586(19) 0.0378(4) Uani 1 1 d . . . . .
H15 H 0.586471 0.196193 0.407911 0.045 Uiso 1 1 calc R U . . .
C23 C 0.63646(19) 0.50576(12) 0.14484(19) 0.0405(5) Uani 1 1 d . . . . .
H23 H 0.588325 0.545641 0.100459 0.049 Uiso 1 1 calc R U . . .
C16 C 0.69290(18) 0.11549(12) 0.3675(2) 0.0414(5) Uani 1 1 d . . . . .
H16 H 0.677223 0.079099 0.427372 0.050 Uiso 1 1 calc R U . . .
C13 C 0.33128(19) 0.41679(12) 0.5359(2) 0.0426(5) Uani 1 1 d . . . . .
H13 H 0.295360 0.440337 0.596345 0.051 Uiso 1 1 calc R U . . .
C12 C 0.45195(19) 0.42087(12) 0.5537(2) 0.0415(5) Uani 1 1 d . . . . .
H12 H 0.497448 0.446961 0.629129 0.050 Uiso 1 1 calc R U . . .
C25 C 0.82226(18) 0.45734(12) 0.2529(2) 0.0457(5) Uani 1 1 d . . . . .
H25 H 0.903805 0.463414 0.282908 0.055 Uiso 1 1 calc R U . . .
C7 C 0.28261(18) 0.26913(12) 0.1448(2) 0.0424(5) Uani 1 1 d . . . . .
H7 H 0.230878 0.241933 0.075452 0.051 Uiso 1 1 calc R U . . .
C17 C 0.76978(17) 0.09761(11) 0.2936(2) 0.0409(5) Uani 1 1 d . . . . .
C8 C 0.40316(18) 0.27308(12) 0.1537(2) 0.0425(5) Uani 1 1 d . . . . .
H8 H 0.430672 0.248459 0.087212 0.051 Uiso 1 1 calc R U . . .
C1 C -0.02313(19) 0.31846(15) 0.0576(2) 0.0527(6) Uani 1 1 d . . . . .
H1A H 0.032592 0.320744 0.003991 0.079 Uiso 1 1 calc R U . . .
H1B H -0.043972 0.369946 0.077405 0.079 Uiso 1 1 calc R U . . .
H1C H -0.092730 0.291495 0.008215 0.079 Uiso 1 1 calc R U . . .
C24 C 0.7553(2) 0.51656(12) 0.1844(2) 0.0438(5) Uani 1 1 d . . . . .
C2 C 0.03026(17) 0.27721(13) 0.1854(2) 0.0436(5) Uani 1 1 d . . . . .
H2A H -0.026752 0.274892 0.238656 0.052 Uiso 1 1 calc R U . . .
H2B H 0.047957 0.224624 0.164636 0.052 Uiso 1 1 calc R U . . .
C20 C 0.8325(2) 0.02266(13) 0.3121(3) 0.0587(7) Uani 1 1 d . . . . .
H20A H 0.860425 0.011810 0.233972 0.088 Uiso 1 1 calc R U . . .
H20B H 0.779502 -0.017497 0.323258 0.088 Uiso 1 1 calc R U . . .
H20C H 0.898404 0.025006 0.391088 0.088 Uiso 1 1 calc R U . . .
C27 C 0.8088(3) 0.59038(14) 0.1588(3) 0.0621(7) Uani 1 1 d . . . . .
H27A H 0.808466 0.593237 0.065033 0.093 Uiso 1 1 calc R U . . .
H27B H 0.888681 0.593178 0.214287 0.093 Uiso 1 1 calc R U . . .
H27C H 0.764101 0.632658 0.180343 0.093 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 C3 1.217(2) . ?
N1 C3 1.393(3) . ?
N1 C6 1.400(2) . ?
N1 C2 1.457(3) . ?
N2 C14 1.421(2) . ?
N2 C9 1.433(2) . ?
N2 C21 1.408(2) . ?
C10 C5 1.393(3) . ?
C10 C9 1.430(3) . ?
C10 C11 1.411(3) . ?
C19 H19 0.9500 . ?
C19 C14 1.391(3) . ?
C19 C18 1.388(3) . ?
C14 C15 1.387(3) . ?
C5 C4 1.394(3) . ?
C5 C6 1.405(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.391(3) . ?
C22 C23 1.389(3) . ?
C4 C3 1.498(3) . ?
C4 C13 1.370(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.389(3) . ?
C9 C8 1.373(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C21 C26 1.398(3) . ?
C6 C7 1.360(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.382(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.410(3) . ?
C12 H12 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.425(3) . ?
C17 C20 1.510(3) . ?
C8 H8 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.507(3) . ?
C24 C27 1.509(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C3 N1 C6 110.88(16) . . ?
C3 N1 C2 124.50(17) . . ?
C6 N1 C2 124.55(17) . . ?
C14 N2 C9 117.50(15) . . ?
C21 N2 C14 123.20(16) . . ?
C21 N2 C9 118.66(15) . . ?
C5 C10 C9 115.26(17) . . ?
C5 C10 C11 115.05(17) . . ?
C11 C10 C9 129.65(17) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C14 120.26(18) . . ?
C19 C14 N2 121.69(18) . . ?
C15 C14 N2 119.71(17) . . ?
C15 C14 C19 118.58(18) . . ?
C10 C5 C4 124.97(18) . . ?
C10 C5 C6 124.88(17) . . ?
C4 C5 C6 110.12(17) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C23 C22 C21 120.59(19) . . ?
C5 C4 C3 106.24(17) . . ?
C13 C4 C5 119.25(18) . . ?
C13 C4 C3 134.43(19) . . ?
C19 C18 H18 119.3 . . ?
C19 C18 C17 121.45(19) . . ?
C17 C18 H18 119.3 . . ?
C10 C9 N2 119.71(17) . . ?
C8 C9 N2 120.68(18) . . ?
C8 C9 C10 119.61(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.35(18) . . ?
C12 C11 H11 119.8 . . ?
O1 C3 N1 124.9(2) . . ?
O1 C3 C4 129.6(2) . . ?
N1 C3 C4 105.45(16) . . ?
C22 C21 N2 120.58(17) . . ?
C22 C21 C26 118.09(18) . . ?
C26 C21 N2 121.29(18) . . ?
N1 C6 C5 107.30(16) . . ?
C7 C6 N1 133.39(18) . . ?
C7 C6 C5 119.29(18) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.63(19) . . ?
C16 C15 H15 119.7 . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.8(2) . . ?
C24 C23 H23 119.1 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.36(19) . . ?
C17 C16 H16 119.3 . . ?
C4 C13 H13 121.3 . . ?
C4 C13 C12 117.36(18) . . ?
C12 C13 H13 121.3 . . ?
C11 C12 C13 123.00(19) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C26 C25 H25 119.1 . . ?
C26 C25 C24 121.8(2) . . ?
C24 C25 H25 119.1 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.44(18) . . ?
C8 C7 H7 121.3 . . ?
C18 C17 C20 121.6(2) . . ?
C16 C17 C18 117.68(18) . . ?
C16 C17 C20 120.7(2) . . ?
C9 C8 C7 123.51(19) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
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 . . ?
C23 C24 C25 117.09(19) . . ?
C23 C24 C27 121.2(2) . . ?
C25 C24 C27 121.7(2) . . ?
N1 C2 C1 113.26(18) . . ?
N1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C6 C7 C8 -178.1(2) . . . . ?
N2 C14 C15 C16 179.80(18) . . . . ?
N2 C9 C8 C7 178.3(2) . . . . ?
N2 C21 C26 C25 179.7(2) . . . . ?
C10 C5 C4 C3 -176.89(17) . . . . ?
C10 C5 C4 C13 0.2(3) . . . . ?
C10 C5 C6 N1 177.37(17) . . . . ?
C10 C5 C6 C7 -1.1(3) . . . . ?
C10 C9 C8 C7 -1.0(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C19 C14 C15 C16 1.3(3) . . . . ?
C19 C18 C17 C16 0.6(3) . . . . ?
C19 C18 C17 C20 -177.73(19) . . . . ?
C14 N2 C9 C10 119.5(2) . . . . ?
C14 N2 C9 C8 -59.8(3) . . . . ?
C14 N2 C21 C22 151.59(19) . . . . ?
C14 N2 C21 C26 -30.8(3) . . . . ?
C14 C19 C18 C17 1.0(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C5 C10 C9 N2 -179.46(16) . . . . ?
C5 C10 C9 C8 -0.2(3) . . . . ?
C5 C10 C11 C12 -0.8(3) . . . . ?
C5 C4 C3 O1 176.6(2) . . . . ?
C5 C4 C3 N1 -1.1(2) . . . . ?
C5 C4 C13 C12 -1.3(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C22 C21 C26 C25 -2.6(3) . . . . ?
C22 C23 C24 C25 -2.0(3) . . . . ?
C22 C23 C24 C27 -179.7(2) . . . . ?
C4 C5 C6 N1 -0.5(2) . . . . ?
C4 C5 C6 C7 -179.05(18) . . . . ?
C4 C13 C12 C11 1.3(3) . . . . ?
C18 C19 C14 N2 179.64(17) . . . . ?
C18 C19 C14 C15 -1.9(3) . . . . ?
C9 N2 C14 C19 135.1(2) . . . . ?
C9 N2 C14 C15 -43.3(3) . . . . ?
C9 N2 C21 C22 -19.0(3) . . . . ?
C9 N2 C21 C26 158.55(19) . . . . ?
C9 C10 C5 C4 178.87(18) . . . . ?
C9 C10 C5 C6 1.3(3) . . . . ?
C9 C10 C11 C12 -178.51(19) . . . . ?
C11 C10 C5 C4 0.8(3) . . . . ?
C11 C10 C5 C6 -176.76(17) . . . . ?
C11 C10 C9 N2 -1.8(3) . . . . ?
C11 C10 C9 C8 177.5(2) . . . . ?
C3 N1 C6 C5 -0.2(2) . . . . ?
C3 N1 C6 C7 178.0(2) . . . . ?
C3 N1 C2 C1 104.6(2) . . . . ?
C3 C4 C13 C12 174.8(2) . . . . ?
C21 N2 C14 C19 -35.6(3) . . . . ?
C21 N2 C14 C15 146.0(2) . . . . ?
C21 N2 C9 C10 -69.4(2) . . . . ?
C21 N2 C9 C8 111.4(2) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C21 C26 C25 C24 1.1(3) . . . . ?
C6 N1 C3 O1 -177.07(19) . . . . ?
C6 N1 C3 C4 0.8(2) . . . . ?
C6 N1 C2 C1 -78.6(3) . . . . ?
C6 C5 C4 C3 1.0(2) . . . . ?
C6 C5 C4 C13 178.15(17) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C26 C25 C24 C23 1.2(3) . . . . ?
C26 C25 C24 C27 179.0(2) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C15 C16 C17 C20 177.13(19) . . . . ?
C23 C22 C21 N2 179.55(18) . . . . ?
C23 C22 C21 C26 1.9(3) . . . . ?
C13 C4 C3 O1 0.1(4) . . . . ?
C13 C4 C3 N1 -177.6(2) . . . . ?
C2 N1 C3 O1 0.2(3) . . . . ?
C2 N1 C3 C4 178.04(17) . . . . ?
C2 N1 C6 C5 -177.44(17) . . . . ?
C2 N1 C6 C7 0.8(3) . . . . ?

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

data_jiayangji-1
_database_code_depnum_ccdc_archive 'CCDC 2352012'
loop_
_audit_author_name
_audit_author_address
'Weihan Guo'
;Nanchang University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2024-04-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.089(C27 H24 N2 O3)'
_chemical_formula_sum            'C27 H24 N2 O3'
_chemical_formula_weight         424.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4592(12)
_cell_length_b                   11.5200(13)
_cell_length_c                   19.198(2)
_cell_angle_alpha                85.698(5)
_cell_angle_beta                 85.659(5)
_cell_angle_gamma                63.308(4)
_cell_volume                     2255.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.39
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            71105
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         2.847
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6367
_reflns_number_total             10428
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         10391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0830
_refine_ls_restrained_S_all      1.067
_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)+(0.0705P)²+3.5153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2098
_refine_ls_wR_factor_ref         0.2335
_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:
 C39(H39A,H39B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C26(H26), C25(H25), C53(H53), C43(H43), C22(H22), C28(H28),
 C42(H42), C23(H23), C16(H16), C45(H45), C6(H6), C46(H46), C30(H30), C49(H49),
 C15(H15), C9(H9), C5(H5), C34(H34), C14(H14), C52(H52), C50(H50), C36(H36),
 C35(H35), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C18(H18A,H18B,H18C), C54(H54A,H54B,H54C), C47(H47A,H47B,
 H47C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_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
O2 O 0.3275(3) 0.1509(3) 0.84067(16) 0.0585(7) Uani 1 1 d . . . . .
O6 O 0.5832(3) 1.3161(3) 0.65940(16) 0.0586(7) Uani 1 1 d . . . . .
O4 O 1.0700(3) 0.2100(2) 0.51912(16) 0.0634(8) Uani 1 1 d . . . . .
O1 O -0.2871(2) 1.0671(3) 0.98393(16) 0.0659(8) Uani 1 1 d . . . . .
N2 N 1.0274(3) 0.3665(3) 0.59916(16) 0.0429(7) Uani 1 1 d . . . . .
O3 O 0.8518(3) 0.6099(3) 0.83158(16) 0.0616(8) Uani 1 1 d . . . . .
N3 N 0.3703(3) 0.6012(3) 0.88987(17) 0.0445(7) Uani 1 1 d . . . . .
N1 N 0.5800(3) 0.8457(3) 0.61087(17) 0.0439(7) Uani 1 1 d . . . . .
O5 O 0.1220(3) 0.7889(3) 0.66494(19) 0.0741(9) Uani 1 1 d . . . . .
N4 N -0.1138(3) 1.0433(3) 0.90604(16) 0.0448(7) Uani 1 1 d . . . . .
C3 C 0.0367(3) 0.8453(3) 0.94189(17) 0.0361(7) Uani 1 1 d . . . . .
C21 C 0.4912(3) 0.6061(3) 0.87446(18) 0.0377(7) Uani 1 1 d . . . . .
C33 C 0.7248(3) 0.6407(3) 0.55430(18) 0.0367(7) Uani 1 1 d . . . . .
C8 C 0.1524(3) 0.7298(3) 0.94584(18) 0.0379(7) Uani 1 1 d . . . . .
C31 C 0.9284(3) 0.4921(3) 0.61216(18) 0.0377(7) Uani 1 1 d . . . . .
C48 C 0.4624(3) 0.8323(3) 0.62406(18) 0.0387(8) Uani 1 1 d . . . . .
C12 C 0.3595(3) 0.4858(3) 0.87760(19) 0.0388(8) Uani 1 1 d . . . . .
C32 C 0.8388(3) 0.5253(3) 0.55917(17) 0.0351(7) Uani 1 1 d . . . . .
C41 C 0.5830(3) 0.9639(3) 0.62392(18) 0.0383(7) Uani 1 1 d . . . . .
C4 C 0.0139(3) 0.9475(3) 0.89246(18) 0.0382(7) Uani 1 1 d . . . . .
C13 C 0.2643(3) 0.4874(3) 0.8368(2) 0.0452(9) Uani 1 1 d . . . . .
H13 H 0.206658 0.565478 0.815479 0.054 Uiso 1 1 calc R U . . .
C26 C 0.5836(3) 0.5256(3) 0.82663(19) 0.0407(8) Uani 1 1 d . . . . .
H26 H 0.565791 0.468355 0.802907 0.049 Uiso 1 1 calc R U . . .
C29 C 0.7003(3) 0.7291(3) 0.60910(19) 0.0385(8) Uani 1 1 d . . . . .
C7 C 0.2521(3) 0.7191(3) 0.89274(19) 0.0384(8) Uani 1 1 d . . . . .
C24 C 0.7302(3) 0.6148(3) 0.84810(19) 0.0422(8) Uani 1 1 d . . . . .
C25 C 0.7026(3) 0.5298(3) 0.81385(19) 0.0425(8) Uani 1 1 d . . . . .
H25 H 0.764060 0.474757 0.781945 0.051 Uiso 1 1 calc R U . . .
C53 C 0.4606(3) 0.7270(3) 0.6628(2) 0.0457(9) Uani 1 1 d . . . . .
H53 H 0.537440 0.663686 0.681300 0.055 Uiso 1 1 calc R U . . .
C43 C 0.4995(3) 1.1650(3) 0.68251(19) 0.0425(8) Uani 1 1 d . . . . .
H43 H 0.440483 1.221619 0.714675 0.051 Uiso 1 1 calc R U . . .
C17 C 0.3426(3) 0.2576(3) 0.8558(2) 0.0437(8) Uani 1 1 d . . . . .
C22 C 0.5204(3) 0.6909(3) 0.90850(19) 0.0442(8) Uani 1 1 d . . . . .
H22 H 0.459522 0.745648 0.940694 0.053 Uiso 1 1 calc R U . . .
C2 C -0.0731(3) 0.8742(4) 0.98698(19) 0.0422(8) Uani 1 1 d . . . . .
C28 C 0.7891(3) 0.6959(3) 0.65937(19) 0.0429(8) Uani 1 1 d . . . . .
H28 H 0.771852 0.754312 0.694145 0.051 Uiso 1 1 calc R U . . .
C42 C 0.4973(3) 1.0492(3) 0.67234(19) 0.0426(8) Uani 1 1 d . . . . .
H42 H 0.437391 1.027702 0.698344 0.051 Uiso 1 1 calc R U . . .
C23 C 0.6389(4) 0.6955(4) 0.8954(2) 0.0459(8) Uani 1 1 d . . . . .
H23 H 0.656729 0.753318 0.918642 0.055 Uiso 1 1 calc R U . . .
C16 C 0.4388(3) 0.2536(3) 0.8968(2) 0.0447(9) Uani 1 1 d . . . . .
H16 H 0.498221 0.174860 0.916737 0.054 Uiso 1 1 calc R U . . .
C45 C 0.6769(3) 1.1135(4) 0.5977(2) 0.0465(9) Uani 1 1 d . . . . .
H45 H 0.738675 1.133947 0.572978 0.056 Uiso 1 1 calc R U . . .
C37 C 0.8796(3) 0.4248(3) 0.51295(18) 0.0400(8) Uani 1 1 d . . . . .
C38 C 1.0035(3) 0.3190(3) 0.5405(2) 0.0452(9) Uani 1 1 d . . . . .
C6 C 0.2296(3) 0.8209(3) 0.8452(2) 0.0431(8) Uani 1 1 d . . . . .
H6 H 0.296009 0.812869 0.812084 0.052 Uiso 1 1 calc R U . . .
C46 C 0.6726(3) 0.9976(4) 0.58717(19) 0.0449(8) Uani 1 1 d . . . . .
H46 H 0.731175 0.941441 0.554678 0.054 Uiso 1 1 calc R U . . .
C30 C 0.9067(3) 0.5774(3) 0.6619(2) 0.0450(8) Uani 1 1 d . . . . .
H30 H 0.966011 0.559424 0.696451 0.054 Uiso 1 1 calc R U . . .
C49 C 0.3462(3) 0.9246(3) 0.5968(2) 0.0478(9) Uani 1 1 d . . . . .
H49 H 0.346089 0.995217 0.569868 0.057 Uiso 1 1 calc R U . . .
C15 C 0.4458(3) 0.3677(3) 0.9080(2) 0.0457(9) Uani 1 1 d . . . . .
H15 H 0.509283 0.365135 0.936364 0.055 Uiso 1 1 calc R U . . .
C9 C 0.1540(4) 0.6408(4) 1.0003(2) 0.0485(9) Uani 1 1 d . . . . .
H9 H 0.228335 0.562225 1.006258 0.058 Uiso 1 1 calc R U . . .
C44 C 0.5895(3) 1.1978(3) 0.64499(19) 0.0419(8) Uani 1 1 d . . . . .
C5 C 0.1111(3) 0.9379(3) 0.8434(2) 0.0450(8) Uani 1 1 d . . . . .
H5 H 0.099921 1.005116 0.810514 0.054 Uiso 1 1 calc R U . . .
C1 C -0.1733(3) 1.0049(4) 0.9619(2) 0.0474(9) Uani 1 1 d . . . . .
C34 C 0.6494(3) 0.6549(4) 0.4966(2) 0.0459(9) Uani 1 1 d . . . . .
H34 H 0.572384 0.730607 0.489671 0.055 Uiso 1 1 calc R U . . .
C14 C 0.2536(4) 0.3762(4) 0.8274(2) 0.0490(9) Uani 1 1 d . . . . .
H14 H 0.186203 0.380041 0.801739 0.059 Uiso 1 1 calc R U . . .
C51 C 0.2307(4) 0.8084(4) 0.6485(2) 0.0520(10) Uani 1 1 d . . . . .
C39 C 1.1327(3) 0.2894(4) 0.6463(2) 0.0514(10) Uani 1 1 d . . . . .
H39A H 1.166618 0.344955 0.663362 0.062 Uiso 1 1 calc R U . . .
H39B H 1.203377 0.221524 0.620557 0.062 Uiso 1 1 calc R U . . .
C52 C 0.3466(4) 0.7144(4) 0.6744(2) 0.0527(10) Uani 1 1 d . . . . .
H52 H 0.347631 0.642019 0.699919 0.063 Uiso 1 1 calc R U . . .
C50 C 0.2305(4) 0.9142(4) 0.6088(2) 0.0531(10) Uani 1 1 d . . . . .
H50 H 0.153482 0.977424 0.590418 0.064 Uiso 1 1 calc R U . . .
C36 C 0.8045(4) 0.4399(4) 0.4573(2) 0.0507(9) Uani 1 1 d . . . . .
H36 H 0.828894 0.375097 0.425442 0.061 Uiso 1 1 calc R U . . .
C35 C 0.6901(4) 0.5563(4) 0.4502(2) 0.0523(9) Uani 1 1 d . . . . .
H35 H 0.638889 0.567954 0.412512 0.063 Uiso 1 1 calc R U . . .
C11 C -0.0703(4) 0.7868(4) 1.0397(2) 0.0542(10) Uani 1 1 d . . . . .
H11 H -0.141786 0.803751 1.070711 0.065 Uiso 1 1 calc R U . . .
C19 C -0.1810(4) 1.1616(4) 0.8628(2) 0.0582(11) Uani 1 1 d . . . . .
H19A H -0.121450 1.199282 0.849568 0.070 Uiso 1 1 calc R U . . .
H19B H -0.254156 1.224176 0.889956 0.070 Uiso 1 1 calc R U . . .
C10 C 0.0456(4) 0.6699(4) 1.0450(2) 0.0580(11) Uani 1 1 d . . . . .
H10 H 0.049219 0.609027 1.080523 0.070 Uiso 1 1 calc R U . . .
C40 C 1.0873(5) 0.2285(5) 0.7076(3) 0.0718(13) Uani 1 1 d . . . . .
H40A H 1.044891 0.181106 0.691074 0.108 Uiso 1 1 calc R U . . .
H40B H 1.026796 0.295240 0.737194 0.108 Uiso 1 1 calc R U . . .
H40C H 1.161120 0.170086 0.733711 0.108 Uiso 1 1 calc R U . . .
C18 C 0.4203(5) 0.0258(4) 0.8656(3) 0.0757(14) Uani 1 1 d . . . . .
H18A H 0.399343 -0.039632 0.850083 0.114 Uiso 1 1 calc R U . . .
H18B H 0.417782 0.022451 0.915766 0.114 Uiso 1 1 calc R U . . .
H18C H 0.506364 0.010279 0.847674 0.114 Uiso 1 1 calc R U . . .
C54 C -0.0006(4) 0.8842(6) 0.6405(4) 0.096(2) Uani 1 1 d . . . . .
H54A H 0.000454 0.883047 0.590500 0.144 Uiso 1 1 calc R U . . .
H54B H -0.015268 0.968696 0.653551 0.144 Uiso 1 1 calc R U . . .
H54C H -0.069360 0.865007 0.660986 0.144 Uiso 1 1 calc R U . . .
C47 C 0.6692(6) 1.3560(5) 0.6200(4) 0.096(2) Uani 1 1 d . . . . .
H47A H 0.648661 1.368018 0.571575 0.145 Uiso 1 1 calc R U . . .
H47B H 0.757638 1.290611 0.624870 0.145 Uiso 1 1 calc R U . . .
H47C H 0.659657 1.436432 0.636631 0.145 Uiso 1 1 calc R U . . .
C20 C -0.2304(6) 1.1369(6) 0.7978(3) 0.0898(17) Uani 1 1 d . . . . .
H20A H -0.268808 1.216057 0.769541 0.135 Uiso 1 1 calc R U . . .
H20B H -0.294918 1.106532 0.810622 0.135 Uiso 1 1 calc R U . . .
H20C H -0.158864 1.072188 0.771770 0.135 Uiso 1 1 calc R U . . .
C27 C 0.8808(5) 0.7015(6) 0.8620(4) 0.103(2) Uani 1 1 d . . . . .
H27A H 0.966445 0.689909 0.845668 0.154 Uiso 1 1 calc R U . . .
H27B H 0.878076 0.688906 0.911941 0.154 Uiso 1 1 calc R U . . .
H27C H 0.817397 0.787896 0.848878 0.154 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
O2 C17 1.370(4) . ?
O2 C18 1.426(5) . ?
O6 C44 1.380(4) . ?
O6 C47 1.414(5) . ?
O4 C38 1.224(4) . ?
O1 C1 1.231(4) . ?
N2 C31 1.407(4) . ?
N2 C38 1.384(5) . ?
N2 C39 1.466(5) . ?
O3 C24 1.383(4) . ?
O3 C27 1.414(6) . ?
N3 C21 1.419(4) . ?
N3 C12 1.427(4) . ?
N3 C7 1.425(4) . ?
N1 C48 1.426(4) . ?
N1 C41 1.419(4) . ?
N1 C29 1.428(4) . ?
O5 C51 1.372(5) . ?
O5 C54 1.427(6) . ?
N4 C4 1.401(4) . ?
N4 C1 1.378(5) . ?
N4 C19 1.457(5) . ?
C3 C8 1.396(4) . ?
C3 C4 1.396(5) . ?
C3 C2 1.394(5) . ?
C21 C26 1.387(5) . ?
C21 C22 1.384(5) . ?
C33 C32 1.386(4) . ?
C33 C29 1.443(5) . ?
C33 C34 1.412(5) . ?
C8 C7 1.441(5) . ?
C8 C9 1.403(5) . ?
C31 C32 1.408(5) . ?
C31 C30 1.351(5) . ?
C48 C53 1.383(5) . ?
C48 C49 1.388(5) . ?
C12 C13 1.383(5) . ?
C12 C15 1.389(5) . ?
C32 C37 1.397(5) . ?
C41 C42 1.388(5) . ?
C41 C46 1.382(5) . ?
C4 C5 1.373(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(5) . ?
C26 H26 0.9300 . ?
C26 C25 1.388(5) . ?
C29 C28 1.363(5) . ?
C7 C6 1.370(5) . ?
C24 C25 1.378(5) . ?
C24 C23 1.376(5) . ?
C25 H25 0.9300 . ?
C53 H53 0.9300 . ?
C53 C52 1.378(5) . ?
C43 H43 0.9300 . ?
C43 C42 1.374(5) . ?
C43 C44 1.385(5) . ?
C17 C16 1.384(5) . ?
C17 C14 1.387(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(5) . ?
C2 C1 1.497(5) . ?
C2 C11 1.364(5) . ?
C28 H28 0.9300 . ?
C28 C30 1.425(5) . ?
C42 H42 0.9300 . ?
C23 H23 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.386(5) . ?
C45 H45 0.9300 . ?
C45 C46 1.388(5) . ?
C45 C44 1.375(5) . ?
C37 C38 1.498(5) . ?
C37 C36 1.374(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.420(5) . ?
C46 H46 0.9300 . ?
C30 H30 0.9300 . ?
C49 H49 0.9300 . ?
C49 C50 1.385(5) . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.378(5) . ?
C5 H5 0.9300 . ?
C34 H34 0.9300 . ?
C34 C35 1.383(5) . ?
C14 H14 0.9300 . ?
C51 C52 1.383(6) . ?
C51 C50 1.388(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.503(6) . ?
C52 H52 0.9300 . ?
C50 H50 0.9300 . ?
C36 H36 0.9300 . ?
C36 C35 1.398(5) . ?
C35 H35 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.408(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.505(7) . ?
C10 H10 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C17 O2 C18 118.5(3) . . ?
C44 O6 C47 117.2(3) . . ?
C31 N2 C39 124.4(3) . . ?
C38 N2 C31 111.1(3) . . ?
C38 N2 C39 124.0(3) . . ?
C24 O3 C27 117.3(3) . . ?
C21 N3 C12 119.6(3) . . ?
C21 N3 C7 119.6(3) . . ?
C7 N3 C12 117.0(3) . . ?
C48 N1 C29 117.4(3) . . ?
C41 N1 C48 120.3(3) . . ?
C41 N1 C29 118.6(3) . . ?
C51 O5 C54 118.2(4) . . ?
C4 N4 C19 125.0(3) . . ?
C1 N4 C4 110.9(3) . . ?
C1 N4 C19 123.7(3) . . ?
C8 C3 C4 125.2(3) . . ?
C2 C3 C8 124.4(3) . . ?
C2 C3 C4 110.4(3) . . ?
C26 C21 N3 121.7(3) . . ?
C22 C21 N3 120.1(3) . . ?
C22 C21 C26 118.2(3) . . ?
C32 C33 C29 115.2(3) . . ?
C32 C33 C34 115.5(3) . . ?
C34 C33 C29 129.3(3) . . ?
C3 C8 C7 115.0(3) . . ?
C3 C8 C9 115.4(3) . . ?
C9 C8 C7 129.6(3) . . ?
N2 C31 C32 106.6(3) . . ?
C30 C31 N2 133.8(3) . . ?
C30 C31 C32 119.6(3) . . ?
C53 C48 N1 121.5(3) . . ?
C53 C48 C49 118.1(3) . . ?
C49 C48 N1 120.4(3) . . ?
C13 C12 N3 122.1(3) . . ?
C13 C12 C15 118.3(3) . . ?
C15 C12 N3 119.5(3) . . ?
C33 C32 C31 124.7(3) . . ?
C33 C32 C37 124.8(3) . . ?
C37 C32 C31 110.5(3) . . ?
C42 C41 N1 122.2(3) . . ?
C46 C41 N1 119.8(3) . . ?
C46 C41 C42 118.0(3) . . ?
C3 C4 N4 107.1(3) . . ?
C5 C4 N4 133.6(3) . . ?
C5 C4 C3 119.3(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C21 C26 H26 119.7 . . ?
C21 C26 C25 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
N1 C29 C33 118.7(3) . . ?
C28 C29 N1 122.1(3) . . ?
C28 C29 C33 119.2(3) . . ?
N3 C7 C8 119.0(3) . . ?
C6 C7 N3 121.7(3) . . ?
C6 C7 C8 119.3(3) . . ?
C25 C24 O3 115.5(3) . . ?
C23 C24 O3 125.1(3) . . ?
C23 C24 C25 119.4(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.8 . . ?
C48 C53 H53 119.5 . . ?
C52 C53 C48 121.0(3) . . ?
C52 C53 H53 119.5 . . ?
C42 C43 H43 119.9 . . ?
C42 C43 C44 120.2(3) . . ?
C44 C43 H43 119.9 . . ?
O2 C17 C16 124.4(3) . . ?
O2 C17 C14 116.1(3) . . ?
C16 C17 C14 119.4(3) . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.1(3) . . ?
C23 C22 H22 119.4 . . ?
C3 C2 C1 105.7(3) . . ?
C11 C2 C3 119.6(3) . . ?
C11 C2 C1 134.8(3) . . ?
C29 C28 H28 118.0 . . ?
C29 C28 C30 124.0(3) . . ?
C30 C28 H28 118.0 . . ?
C41 C42 H42 119.5 . . ?
C43 C42 C41 121.1(3) . . ?
C43 C42 H42 119.5 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C17 C16 H16 120.2 . . ?
C17 C16 C15 119.5(3) . . ?
C15 C16 H16 120.2 . . ?
C46 C45 H45 120.2 . . ?
C44 C45 H45 120.2 . . ?
C44 C45 C46 119.7(3) . . ?
C32 C37 C38 105.8(3) . . ?
C36 C37 C32 118.9(3) . . ?
C36 C37 C38 135.3(3) . . ?
O4 C38 N2 125.1(4) . . ?
O4 C38 C37 128.9(4) . . ?
N2 C38 C37 105.9(3) . . ?
C7 C6 H6 118.0 . . ?
C7 C6 C5 124.1(3) . . ?
C5 C6 H6 118.0 . . ?
C41 C46 C45 121.3(3) . . ?
C41 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?
C31 C30 C28 117.2(3) . . ?
C31 C30 H30 121.4 . . ?
C28 C30 H30 121.4 . . ?
C48 C49 H49 119.2 . . ?
C50 C49 C48 121.6(4) . . ?
C50 C49 H49 119.2 . . ?
C12 C15 H15 119.4 . . ?
C16 C15 C12 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
O6 C44 C43 115.3(3) . . ?
C45 C44 O6 125.0(3) . . ?
C45 C44 C43 119.6(3) . . ?
C4 C5 C6 117.1(3) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
O1 C1 N4 125.4(4) . . ?
O1 C1 C2 128.7(4) . . ?
N4 C1 C2 105.8(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 119.9(3) . . ?
C35 C34 H34 120.0 . . ?
C13 C14 C17 120.5(4) . . ?
C13 C14 H14 119.8 . . ?
C17 C14 H14 119.8 . . ?
O5 C51 C52 116.0(4) . . ?
O5 C51 C50 124.6(4) . . ?
C52 C51 C50 119.5(3) . . ?
N2 C39 H39A 109.2 . . ?
N2 C39 H39B 109.2 . . ?
N2 C39 C40 112.2(3) . . ?
H39A C39 H39B 107.9 . . ?
C40 C39 H39A 109.2 . . ?
C40 C39 H39B 109.2 . . ?
C53 C52 C51 120.5(4) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C49 C50 C51 119.3(4) . . ?
C49 C50 H50 120.4 . . ?
C51 C50 H50 120.4 . . ?
C37 C36 H36 121.2 . . ?
C37 C36 C35 117.7(3) . . ?
C35 C36 H36 121.2 . . ?
C34 C35 C36 123.2(4) . . ?
C34 C35 H35 118.4 . . ?
C36 C35 H35 118.4 . . ?
C2 C11 H11 121.5 . . ?
C2 C11 C10 117.1(3) . . ?
C10 C11 H11 121.5 . . ?
N4 C19 H19A 109.1 . . ?
N4 C19 H19B 109.1 . . ?
N4 C19 C20 112.3(4) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C9 C10 C11 123.4(4) . . ?
C9 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C54 H54A 109.5 . . ?
O5 C54 H54B 109.5 . . ?
O5 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O6 C47 H47A 109.5 . . ?
O6 C47 H47B 109.5 . . ?
O6 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
O3 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
O2 C17 C16 C15 179.2(3) . . . . ?
O2 C17 C14 C13 -176.9(3) . . . . ?
N2 C31 C32 C33 178.2(3) . . . . ?
N2 C31 C32 C37 -0.7(4) . . . . ?
N2 C31 C30 C28 -177.0(4) . . . . ?
O3 C24 C25 C26 179.6(3) . . . . ?
O3 C24 C23 C22 -179.2(3) . . . . ?
N3 C21 C26 C25 -178.2(3) . . . . ?
N3 C21 C22 C23 178.6(3) . . . . ?
N3 C12 C13 C14 -178.2(3) . . . . ?
N3 C12 C15 C16 -179.5(3) . . . . ?
N3 C7 C6 C5 176.7(3) . . . . ?
N1 C48 C53 C52 -179.2(3) . . . . ?
N1 C48 C49 C50 -180.0(3) . . . . ?
N1 C41 C42 C43 -178.0(3) . . . . ?
N1 C41 C46 C45 178.9(3) . . . . ?
N1 C29 C28 C30 176.3(3) . . . . ?
O5 C51 C52 C53 -177.9(4) . . . . ?
O5 C51 C50 C49 178.7(4) . . . . ?
N4 C4 C5 C6 -178.4(4) . . . . ?
C3 C8 C7 N3 -176.0(3) . . . . ?
C3 C8 C7 C6 2.3(5) . . . . ?
C3 C8 C9 C10 0.6(6) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
C3 C2 C1 O1 176.7(4) . . . . ?
C3 C2 C1 N4 -1.6(4) . . . . ?
C3 C2 C11 C10 -0.4(6) . . . . ?
C21 N3 C12 C13 -125.6(4) . . . . ?
C21 N3 C12 C15 55.3(5) . . . . ?
C21 N3 C7 C8 -140.9(3) . . . . ?
C21 N3 C7 C6 41.0(5) . . . . ?
C21 C26 C25 C24 -0.5(5) . . . . ?
C21 C22 C23 C24 -0.2(6) . . . . ?
C33 C32 C37 C38 -177.6(3) . . . . ?
C33 C32 C37 C36 1.5(5) . . . . ?
C33 C29 C28 C30 -0.3(5) . . . . ?
C33 C34 C35 C36 0.1(6) . . . . ?
C8 C3 C4 N4 179.2(3) . . . . ?
C8 C3 C4 C5 -0.7(5) . . . . ?
C8 C3 C2 C1 -178.4(3) . . . . ?
C8 C3 C2 C11 0.8(6) . . . . ?
C8 C7 C6 C5 -1.5(6) . . . . ?
C8 C9 C10 C11 -0.3(7) . . . . ?
C31 N2 C38 O4 -176.2(4) . . . . ?
C31 N2 C38 C37 1.1(4) . . . . ?
C31 N2 C39 C40 77.8(5) . . . . ?
C31 C32 C37 C38 1.4(4) . . . . ?
C31 C32 C37 C36 -179.6(3) . . . . ?
C48 N1 C41 C42 25.3(5) . . . . ?
C48 N1 C41 C46 -154.0(3) . . . . ?
C48 N1 C29 C33 65.3(4) . . . . ?
C48 N1 C29 C28 -111.3(4) . . . . ?
C48 C53 C52 C51 -1.2(6) . . . . ?
C48 C49 C50 C51 -0.5(6) . . . . ?
C12 N3 C21 C26 23.1(5) . . . . ?
C12 N3 C21 C22 -155.6(3) . . . . ?
C12 N3 C7 C8 61.2(4) . . . . ?
C12 N3 C7 C6 -117.0(4) . . . . ?
C12 C13 C14 C17 -3.3(6) . . . . ?
C32 C33 C29 N1 -175.3(3) . . . . ?
C32 C33 C29 C28 1.4(5) . . . . ?
C32 C33 C34 C35 1.1(5) . . . . ?
C32 C31 C30 C28 2.6(5) . . . . ?
C32 C37 C38 O4 175.7(4) . . . . ?
C32 C37 C38 N2 -1.5(4) . . . . ?
C32 C37 C36 C35 -0.2(5) . . . . ?
C41 N1 C48 C53 -129.9(4) . . . . ?
C41 N1 C48 C49 51.4(5) . . . . ?
C41 N1 C29 C33 -136.2(3) . . . . ?
C41 N1 C29 C28 47.1(5) . . . . ?
C4 N4 C1 O1 -177.0(4) . . . . ?
C4 N4 C1 C2 1.4(4) . . . . ?
C4 N4 C19 C20 77.4(5) . . . . ?
C4 C3 C8 C7 -1.2(5) . . . . ?
C4 C3 C8 C9 179.4(3) . . . . ?
C4 C3 C2 C1 1.3(4) . . . . ?
C4 C3 C2 C11 -179.4(4) . . . . ?
C13 C12 C15 C16 1.3(5) . . . . ?
C26 C21 C22 C23 -0.1(5) . . . . ?
C29 N1 C48 C53 28.1(5) . . . . ?
C29 N1 C48 C49 -150.6(3) . . . . ?
C29 N1 C41 C42 -132.5(4) . . . . ?
C29 N1 C41 C46 48.2(5) . . . . ?
C29 C33 C32 C31 -0.6(5) . . . . ?
C29 C33 C32 C37 178.2(3) . . . . ?
C29 C33 C34 C35 -179.0(4) . . . . ?
C29 C28 C30 C31 -1.8(6) . . . . ?
C7 N3 C21 C26 -134.3(4) . . . . ?
C7 N3 C21 C22 47.0(5) . . . . ?
C7 N3 C12 C13 32.4(5) . . . . ?
C7 N3 C12 C15 -146.7(3) . . . . ?
C7 C8 C9 C10 -178.7(4) . . . . ?
C7 C6 C5 C4 -0.5(6) . . . . ?
C25 C24 C23 C22 0.2(6) . . . . ?
C53 C48 C49 C50 1.2(6) . . . . ?
C17 C16 C15 C12 -1.3(5) . . . . ?
C22 C21 C26 C25 0.5(5) . . . . ?
C2 C3 C8 C7 178.5(3) . . . . ?
C2 C3 C8 C9 -0.9(5) . . . . ?
C2 C3 C4 N4 -0.5(4) . . . . ?
C2 C3 C4 C5 179.5(3) . . . . ?
C2 C11 C10 C9 0.2(7) . . . . ?
C42 C41 C46 C45 -0.4(5) . . . . ?
C42 C43 C44 O6 -179.9(3) . . . . ?
C42 C43 C44 C45 -0.3(6) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
C16 C17 C14 C13 3.2(6) . . . . ?
C37 C36 C35 C34 -0.5(6) . . . . ?
C38 N2 C31 C32 -0.3(4) . . . . ?
C38 N2 C31 C30 179.4(4) . . . . ?
C38 N2 C39 C40 -94.0(4) . . . . ?
C38 C37 C36 C35 178.5(4) . . . . ?
C46 C41 C42 C43 1.3(5) . . . . ?
C46 C45 C44 O6 -179.2(3) . . . . ?
C46 C45 C44 C43 1.2(6) . . . . ?
C30 C31 C32 C33 -1.5(5) . . . . ?
C30 C31 C32 C37 179.6(3) . . . . ?
C49 C48 C53 C52 -0.4(5) . . . . ?
C15 C12 C13 C14 1.0(5) . . . . ?
C9 C8 C7 N3 3.3(6) . . . . ?
C9 C8 C7 C6 -178.5(4) . . . . ?
C44 C43 C42 C41 -1.0(6) . . . . ?
C44 C45 C46 C41 -0.9(6) . . . . ?
C1 N4 C4 C3 -0.6(4) . . . . ?
C1 N4 C4 C5 179.3(4) . . . . ?
C1 N4 C19 C20 -95.5(5) . . . . ?
C1 C2 C11 C10 178.6(4) . . . . ?
C34 C33 C32 C31 179.3(3) . . . . ?
C34 C33 C32 C37 -1.9(5) . . . . ?
C34 C33 C29 N1 4.8(5) . . . . ?
C34 C33 C29 C28 -178.5(4) . . . . ?
C14 C17 C16 C15 -0.9(5) . . . . ?
C39 N2 C31 C32 -173.0(3) . . . . ?
C39 N2 C31 C30 6.7(6) . . . . ?
C39 N2 C38 O4 -3.5(6) . . . . ?
C39 N2 C38 C37 173.8(3) . . . . ?
C52 C51 C50 C49 -1.0(6) . . . . ?
C50 C51 C52 C53 1.9(6) . . . . ?
C36 C37 C38 O4 -3.1(7) . . . . ?
C36 C37 C38 N2 179.7(4) . . . . ?
C11 C2 C1 O1 -2.5(7) . . . . ?
C11 C2 C1 N4 179.2(4) . . . . ?
C19 N4 C4 C3 -174.3(3) . . . . ?
C19 N4 C4 C5 5.7(7) . . . . ?
C19 N4 C1 O1 -3.2(6) . . . . ?
C19 N4 C1 C2 175.2(3) . . . . ?
C18 O2 C17 C16 -3.3(5) . . . . ?
C18 O2 C17 C14 176.9(4) . . . . ?
C54 O5 C51 C52 178.9(4) . . . . ?
C54 O5 C51 C50 -0.8(6) . . . . ?
C47 O6 C44 C43 -177.2(4) . . . . ?
C47 O6 C44 C45 3.2(6) . . . . ?
C27 O3 C24 C25 175.8(4) . . . . ?
C27 O3 C24 C23 -4.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_jiayangji-1         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 12 Note 
RESPONSE: The missing FCF reflections below theta(min) were caused 
by the high beamstop theta(min) limit set.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_220808a
_database_code_depnum_ccdc_archive 'CCDC 2352009'
loop_
_audit_author_name
_audit_author_address
'Weihan Guo'
;Nanchang University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 N2 O'
_chemical_formula_sum            'C25 H20 N2 O'
_chemical_formula_weight         364.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.418(15)
_cell_length_b                   10.444(17)
_cell_length_c                   10.672(17)
_cell_angle_alpha                68.47(2)
_cell_angle_beta                 74.62(2)
_cell_angle_gamma                73.96(2)
_cell_volume                     923(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    677
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      25.324
_cell_measurement_theta_min      2.289
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1242 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.5934.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.13
_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  0.1890
_diffrn_reflns_av_unetI/netI     0.2416
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8027
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.499
_diffrn_reflns_theta_max         24.499
_diffrn_reflns_theta_min         2.087
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1092
_reflns_number_total             3054
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker SMART APEX II diffractrometer'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2611
_refine_ls_R_factor_gt           0.0953
_refine_ls_restrained_S_all      0.966
_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)+(0.0816P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.2387
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C7(H7), C11(H11), C5(H5)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_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
N2 N 0.3710(5) 0.5518(5) 0.2570(5) 0.0612(15) Uani 1 1 d . . . . .
O1 O -0.0759(5) 1.2423(4) 0.0638(5) 0.0858(16) Uani 1 1 d . . . . .
C13 C 0.1420(7) 0.9095(6) 0.1592(7) 0.0506(16) Uani 1 1 d . . . . .
C12 C 0.0193(7) 0.9005(6) 0.2646(7) 0.0508(16) Uani 1 1 d . . . . .
C14 C 0.5130(7) 0.5574(6) 0.2654(7) 0.0524(17) Uani 1 1 d . . . . .
C15 C 0.5344(8) 0.6289(7) 0.3420(7) 0.0585(19) Uani 1 1 d . . . . .
H15 H 0.449(6) 0.672(6) 0.389(6) 0.070 Uiso 1 1 d . U . . .
C16 C 0.6747(10) 0.6347(8) 0.3477(8) 0.073(2) Uani 1 1 d . . . . .
H16 H 0.689(8) 0.678(7) 0.391(8) 0.088 Uiso 1 1 d . U . . .
C17 C 0.7978(8) 0.5676(8) 0.2778(8) 0.067(2) Uani 1 1 d . . . . .
H17 H 0.889(7) 0.581(6) 0.281(6) 0.080 Uiso 1 1 d . U . . .
C18 C 0.7774(8) 0.4977(7) 0.2031(9) 0.070(2) Uani 1 1 d . . . . .
H18 H 0.858(7) 0.462(6) 0.147(6) 0.084 Uiso 1 1 d . U . . .
C19 C 0.6392(8) 0.4915(6) 0.1952(8) 0.065(2) Uani 1 1 d . . . . .
H19 H 0.624(6) 0.444(6) 0.141(6) 0.078 Uiso 1 1 d . U . . .
C20 C 0.3356(6) 0.4321(6) 0.2542(6) 0.0511(17) Uani 1 1 d . . . . .
C21 C 0.4058(7) 0.3010(7) 0.3295(7) 0.0598(19) Uani 1 1 d . . . . .
H21 H 0.486(6) 0.290(5) 0.388(6) 0.072 Uiso 1 1 d . U . . .
C22 C 0.3705(8) 0.1844(7) 0.3239(8) 0.066(2) Uani 1 1 d . . . . .
H22 H 0.419(6) 0.101(6) 0.384(6) 0.079 Uiso 1 1 d . U . . .
C23 C 0.2672(8) 0.1909(7) 0.2531(8) 0.075(2) Uani 1 1 d . . . . .
H23 H 0.242(6) 0.101(6) 0.260(6) 0.090 Uiso 1 1 d . U . . .
C24 C 0.1997(8) 0.3235(8) 0.1799(8) 0.075(2) Uani 1 1 d . . . . .
H24 H 0.126(7) 0.315(6) 0.130(6) 0.090 Uiso 1 1 d . U . . .
C25 C 0.2307(7) 0.4418(7) 0.1827(7) 0.065(2) Uani 1 1 d . . . . .
H25 H 0.194(6) 0.547(6) 0.118(6) 0.078 Uiso 1 1 d . U . . .
N1 N -0.0763(6) 1.0327(5) 0.2351(6) 0.0627(15) Uani 1 1 d . . . . .
C8 C 0.2617(7) 0.7986(6) 0.1508(7) 0.0550(17) Uani 1 1 d . . . . .
C10 C 0.1316(7) 0.6649(6) 0.3615(7) 0.0624(19) Uani 1 1 d . . . . .
H10 H 0.128452 0.579712 0.431505 0.075 Uiso 1 1 calc R U . . .
C9 C 0.2528(7) 0.6728(6) 0.2577(7) 0.0551(17) Uani 1 1 d . . . . .
C6 C 0.3617(7) 0.9609(7) -0.0576(7) 0.076(2) Uani 1 1 d . . . . .
H6 H 0.439059 0.978863 -0.132754 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3723(7) 0.8308(7) 0.0358(8) 0.066(2) Uani 1 1 d . . . . .
H7 H 0.455812 0.761458 0.022422 0.079 Uiso 1 1 calc R U . . .
C3 C -0.0162(8) 1.1219(7) 0.1136(8) 0.064(2) Uani 1 1 d . . . . .
C4 C 0.1266(8) 1.0400(6) 0.0653(7) 0.0575(18) Uani 1 1 d . . . . .
C11 C 0.0086(7) 0.7801(7) 0.3691(7) 0.0629(19) Uani 1 1 d . . . . .
H11 H -0.073040 0.772395 0.441173 0.075 Uiso 1 1 calc R U . . .
C1 C -0.2165(7) 1.0728(6) 0.3186(7) 0.074(2) Uani 1 1 d . . . . .
H1A H -0.267517 0.994065 0.359893 0.089 Uiso 1 1 calc R U . . .
H1B H -0.279876 1.149462 0.261378 0.089 Uiso 1 1 calc R U . . .
C2 C -0.1943(8) 1.1182(7) 0.4309(7) 0.086(2) Uani 1 1 d . . . . .
H2A H -0.139806 1.193357 0.390631 0.128 Uiso 1 1 calc R U . . .
H2B H -0.138601 1.040195 0.492192 0.128 Uiso 1 1 calc R U . . .
H2C H -0.290488 1.149882 0.480864 0.128 Uiso 1 1 calc R U . . .
C5 C 0.2374(8) 1.0697(7) -0.0445(8) 0.075(2) Uani 1 1 d . . . . .
H5 H 0.231766 1.158792 -0.109105 0.090 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
N2 C14 1.381(7) . ?
N2 C20 1.392(7) . ?
N2 C9 1.436(7) . ?
O1 C3 1.207(7) . ?
C13 C12 1.380(8) . ?
C13 C8 1.386(7) . ?
C13 C4 1.360(8) . ?
C12 N1 1.400(7) . ?
C12 C11 1.348(8) . ?
C14 C15 1.373(8) . ?
C14 C19 1.379(8) . ?
C15 H15 0.93(5) . ?
C15 C16 1.358(9) . ?
C16 H16 0.81(6) . ?
C16 C17 1.366(9) . ?
C17 H17 0.92(6) . ?
C17 C18 1.339(9) . ?
C18 H18 0.91(6) . ?
C18 C19 1.347(9) . ?
C19 H19 0.94(6) . ?
C20 C21 1.390(8) . ?
C20 C25 1.363(8) . ?
C21 H21 1.06(5) . ?
C21 C22 1.372(9) . ?
C22 H22 0.95(6) . ?
C22 C23 1.356(9) . ?
C23 H23 1.00(6) . ?
C23 C24 1.384(9) . ?
C24 H24 1.02(6) . ?
C24 C25 1.358(8) . ?
C25 H25 1.07(6) . ?
N1 C3 1.373(8) . ?
N1 C1 1.434(7) . ?
C8 C9 1.394(8) . ?
C8 C7 1.384(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.361(8) . ?
C10 C11 1.431(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.355(8) . ?
C6 C5 1.405(8) . ?
C7 H7 0.9300 . ?
C3 C4 1.458(9) . ?
C4 C5 1.350(8) . ?
C11 H11 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.520(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C5 H5 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
C14 N2 C20 123.0(5) . . ?
C14 N2 C9 118.5(5) . . ?
C20 N2 C9 118.4(5) . . ?
C12 C13 C8 123.9(6) . . ?
C4 C13 C12 110.5(6) . . ?
C4 C13 C8 125.6(7) . . ?
C13 C12 N1 106.5(6) . . ?
C11 C12 C13 121.2(6) . . ?
C11 C12 N1 132.3(7) . . ?
C15 C14 N2 121.9(6) . . ?
C15 C14 C19 117.5(6) . . ?
C19 C14 N2 120.7(6) . . ?
C14 C15 H15 117(3) . . ?
C16 C15 C14 121.1(7) . . ?
C16 C15 H15 122(4) . . ?
C15 C16 H16 122(5) . . ?
C15 C16 C17 120.2(7) . . ?
C17 C16 H16 118(5) . . ?
C16 C17 H17 116(4) . . ?
C18 C17 C16 118.9(7) . . ?
C18 C17 H17 125(4) . . ?
C17 C18 H18 120(4) . . ?
C17 C18 C19 121.8(7) . . ?
C19 C18 H18 118(4) . . ?
C14 C19 H19 117(4) . . ?
C18 C19 C14 120.5(7) . . ?
C18 C19 H19 122(4) . . ?
C21 C20 N2 118.9(6) . . ?
C25 C20 N2 121.2(6) . . ?
C25 C20 C21 119.9(6) . . ?
C20 C21 H21 122(3) . . ?
C22 C21 C20 117.9(7) . . ?
C22 C21 H21 120(3) . . ?
C21 C22 H22 111(4) . . ?
C23 C22 C21 123.4(7) . . ?
C23 C22 H22 125(4) . . ?
C22 C23 H23 119(4) . . ?
C22 C23 C24 116.7(7) . . ?
C24 C23 H23 125(4) . . ?
C23 C24 H24 110(3) . . ?
C25 C24 C23 121.9(7) . . ?
C25 C24 H24 129(3) . . ?
C20 C25 H25 114(3) . . ?
C24 C25 C20 120.0(7) . . ?
C24 C25 H25 125(3) . . ?
C12 N1 C1 125.9(6) . . ?
C3 N1 C12 110.3(6) . . ?
C3 N1 C1 123.8(5) . . ?
C13 C8 C9 115.9(6) . . ?
C7 C8 C13 114.1(6) . . ?
C7 C8 C9 130.0(6) . . ?
C9 C10 H10 118.1 . . ?
C9 C10 C11 123.7(6) . . ?
C11 C10 H10 118.1 . . ?
C8 C9 N2 119.8(6) . . ?
C10 C9 N2 120.3(6) . . ?
C10 C9 C8 119.9(6) . . ?
C7 C6 H6 119.0 . . ?
C7 C6 C5 122.1(7) . . ?
C5 C6 H6 119.0 . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.5(6) . . ?
C6 C7 H7 119.2 . . ?
O1 C3 N1 124.0(7) . . ?
O1 C3 C4 130.4(7) . . ?
N1 C3 C4 105.5(6) . . ?
C13 C4 C3 107.1(6) . . ?
C5 C4 C13 119.2(6) . . ?
C5 C4 C3 133.7(6) . . ?
C12 C11 C10 115.4(6) . . ?
C12 C11 H11 122.3 . . ?
C10 C11 H11 122.3 . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 111.8(6) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C5 H5 121.3 . . ?
C4 C5 C6 117.5(7) . . ?
C4 C5 H5 121.3 . . ?

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
N2 C14 C15 C16 -179.2(6) . . . . ?
N2 C14 C19 C18 179.7(6) . . . . ?
N2 C20 C21 C22 -179.3(6) . . . . ?
N2 C20 C25 C24 179.0(6) . . . . ?
O1 C3 C4 C13 179.9(7) . . . . ?
O1 C3 C4 C5 1.7(12) . . . . ?
C13 C12 N1 C3 0.7(7) . . . . ?
C13 C12 N1 C1 -178.5(6) . . . . ?
C13 C12 C11 C10 -0.4(9) . . . . ?
C13 C8 C9 N2 179.4(5) . . . . ?
C13 C8 C9 C10 0.0(9) . . . . ?
C13 C8 C7 C6 0.7(9) . . . . ?
C13 C4 C5 C6 2.1(10) . . . . ?
C12 C13 C8 C9 -0.3(9) . . . . ?
C12 C13 C8 C7 179.6(6) . . . . ?
C12 C13 C4 C3 0.3(7) . . . . ?
C12 C13 C4 C5 178.8(6) . . . . ?
C12 N1 C3 O1 179.7(6) . . . . ?
C12 N1 C3 C4 -0.5(6) . . . . ?
C12 N1 C1 C2 84.1(7) . . . . ?
C14 N2 C20 C21 34.6(9) . . . . ?
C14 N2 C20 C25 -147.4(6) . . . . ?
C14 N2 C9 C8 63.9(8) . . . . ?
C14 N2 C9 C10 -116.8(7) . . . . ?
C14 C15 C16 C17 -0.7(11) . . . . ?
C15 C14 C19 C18 0.2(10) . . . . ?
C15 C16 C17 C18 0.7(11) . . . . ?
C16 C17 C18 C19 -0.2(11) . . . . ?
C17 C18 C19 C14 -0.3(11) . . . . ?
C19 C14 C15 C16 0.3(9) . . . . ?
C20 N2 C14 C15 -141.9(6) . . . . ?
C20 N2 C14 C19 38.7(9) . . . . ?
C20 N2 C9 C8 -119.0(6) . . . . ?
C20 N2 C9 C10 60.4(8) . . . . ?
C20 C21 C22 C23 -2.4(10) . . . . ?
C21 C20 C25 C24 -3.0(10) . . . . ?
C21 C22 C23 C24 2.3(11) . . . . ?
C22 C23 C24 C25 -2.4(11) . . . . ?
C23 C24 C25 C20 2.9(11) . . . . ?
C25 C20 C21 C22 2.7(9) . . . . ?
N1 C12 C11 C10 179.3(6) . . . . ?
N1 C3 C4 C13 0.1(7) . . . . ?
N1 C3 C4 C5 -178.1(7) . . . . ?
C8 C13 C12 N1 -179.3(5) . . . . ?
C8 C13 C12 C11 0.5(10) . . . . ?
C8 C13 C4 C3 179.0(6) . . . . ?
C8 C13 C4 C5 -2.5(10) . . . . ?
C9 N2 C14 C15 35.1(9) . . . . ?
C9 N2 C14 C19 -144.3(6) . . . . ?
C9 N2 C20 C21 -142.4(6) . . . . ?
C9 N2 C20 C25 35.6(9) . . . . ?
C9 C8 C7 C6 -179.5(6) . . . . ?
C9 C10 C11 C12 0.2(9) . . . . ?
C7 C8 C9 N2 -0.4(10) . . . . ?
C7 C8 C9 C10 -179.7(6) . . . . ?
C7 C6 C5 C4 -0.4(10) . . . . ?
C3 N1 C1 C2 -95.0(7) . . . . ?
C3 C4 C5 C6 -179.9(7) . . . . ?
C4 C13 C12 N1 -0.7(7) . . . . ?
C4 C13 C12 C11 179.1(6) . . . . ?
C4 C13 C8 C9 -178.7(6) . . . . ?
C4 C13 C8 C7 1.1(9) . . . . ?
C11 C12 N1 C3 -179.0(7) . . . . ?
C11 C12 N1 C1 1.8(11) . . . . ?
C11 C10 C9 N2 -179.4(5) . . . . ?
C11 C10 C9 C8 0.0(10) . . . . ?
C1 N1 C3 O1 -1.0(10) . . . . ?
C1 N1 C3 C4 178.7(5) . . . . ?
C5 C6 C7 C8 -1.0(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_RINTA01_220808a             
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Poor quality crystals -several tried, best result presented.
;
_vrf_PLAT020_220808a             
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.189 Report
RESPONSE: Poor quality crystals -several tried, best result presented.
;
_vrf_PLAT026_220808a             
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        36% Check 
RESPONSE: Poor quality crystals -several tried, best result presented.
;
_vrf_PLAT340_220808a             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01076 Ang.  
RESPONSE: Poor quality crystals -several tried, best result presented.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_hong-2
_database_code_depnum_ccdc_archive 'CCDC 2352010'
loop_
_audit_author_name
_audit_author_address
'Weihan Guo'
;Nanchang University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C25 H20 N2 O)'
_chemical_formula_sum            'C100 H80 N8 O4'
_chemical_formula_weight         1457.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3580(2)
_cell_length_b                   12.5546(2)
_cell_length_c                   14.4385(3)
_cell_angle_alpha                104.2940(10)
_cell_angle_beta                 104.552(2)
_cell_angle_gamma                97.3940(10)
_cell_volume                     1890.77(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    13915
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.2680
_cell_measurement_theta_min      1.7380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       stick
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.414
_diffrn_reflns_theta_min         1.710
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6864
_reflns_number_total             8547
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.073
_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)+(0.0498P)²+0.3349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1076
_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:
 C01F(H01A,H01E), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C4(H4), C12(H12), C00M(H00M), C6(H6), C8(H8), C3(H3), C00R(H00R),
 C00S(H00S), C14(H14), C00U(H00U), C00V(H00V), C15(H15), C010(H010), C21(H21),
 C9(H9), C013(H013), C014(H014), C2(H2), C016(H016), C20(H20), C018(H018),
 C1(H1), C11(H11), C01B(H01B), C01C(H01C), C01D(H01D), C10(H10), C01H(H01H),
 C01I(H01I)
2.c Idealised Me refined as rotating group:
 C01J(H01F,H01G,H01J), C25(H25A,H25B,H25C)
;
_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
O001 O 0.48095(8) 0.73412(7) 0.88166(7) 0.0266(2) Uani 1 1 d . . . . .
O1 O -0.50211(8) -0.26467(8) 0.53742(8) 0.0312(2) Uani 1 1 d . . . . .
N1 N -0.14731(9) 0.27373(8) 0.57662(7) 0.0177(2) Uani 1 1 d . . . . .
N004 N 0.39690(9) 0.55053(8) 0.78382(8) 0.0199(2) Uani 1 1 d . . . . .
N005 N 0.17554(9) 0.20647(8) 0.90826(8) 0.0193(2) Uani 1 1 d . . . . .
N2 N -0.38971(9) -0.09796(9) 0.65575(8) 0.0218(2) Uani 1 1 d . . . . .
C17 C -0.33268(10) -0.00268(10) 0.55461(9) 0.0168(2) Uani 1 1 d . . . . .
C18 C -0.27934(10) 0.08274(10) 0.52244(9) 0.0168(2) Uani 1 1 d . . . . .
C7 C -0.05167(10) 0.25671(10) 0.53081(9) 0.0169(2) Uani 1 1 d . . . . .
C00A C 0.19947(11) 0.09566(10) 0.87487(9) 0.0182(2) Uani 1 1 d . . . . .
C00B C 0.33536(11) 0.47761(10) 0.89645(9) 0.0179(2) Uani 1 1 d . . . . .
C00C C 0.33716(11) 0.45230(10) 0.79629(9) 0.0184(3) Uani 1 1 d . . . . .
C16 C -0.32258(11) 0.00364(10) 0.65507(9) 0.0186(3) Uani 1 1 d . . . . .
C00E C 0.39363(11) 0.58927(10) 0.94766(9) 0.0187(3) Uani 1 1 d . . . . .
C19 C -0.30344(11) 0.05807(10) 0.41732(9) 0.0198(3) Uani 1 1 d . . . . .
H19 H -0.270790 0.112354 0.389803 0.024 Uiso 1 1 calc R U . . .
C4 C -0.24029(11) 0.42510(10) 0.65066(9) 0.0192(3) Uani 1 1 d . . . . .
H4 H -0.320027 0.382965 0.609754 0.023 Uiso 1 1 calc R U . . .
C13 C -0.20844(11) 0.18187(10) 0.60038(9) 0.0170(2) Uani 1 1 d . . . . .
C00I C 0.06843(11) 0.21931(10) 0.93896(9) 0.0187(2) Uani 1 1 d . . . . .
C12 C 0.00507(11) 0.16448(10) 0.52994(9) 0.0204(3) Uani 1 1 d . . . . .
H12 H -0.021269 0.109602 0.559497 0.024 Uiso 1 1 calc R U . . .
C22 C -0.40484(11) -0.10603(10) 0.49200(10) 0.0197(3) Uani 1 1 d . . . . .
C5 C -0.13422(11) 0.38311(10) 0.64355(9) 0.0171(2) Uani 1 1 d . . . . .
C00M C -0.09250(11) 0.32196(11) 0.96450(9) 0.0224(3) Uani 1 1 d . . . . .
H00M H -0.129364 0.385077 0.960474 0.027 Uiso 1 1 calc R U . . .
C6 C -0.01767(11) 0.44602(10) 0.70315(9) 0.0206(3) Uani 1 1 d . . . . .
H6 H 0.054889 0.417699 0.698323 0.025 Uiso 1 1 calc R U . . .
C00O C 0.23204(11) 0.29039(10) 0.87294(9) 0.0186(3) Uani 1 1 d . . . . .
C8 C -0.01169(11) 0.33576(10) 0.48593(9) 0.0190(3) Uani 1 1 d . . . . .
H8 H -0.050791 0.398084 0.484561 0.023 Uiso 1 1 calc R U . . .
C3 C -0.22873(12) 0.52900(10) 0.71797(9) 0.0216(3) Uani 1 1 d . . . . .
H3 H -0.301127 0.557405 0.723195 0.026 Uiso 1 1 calc R U . . .
C00R C 0.01794(11) 0.14081(10) 0.97974(9) 0.0212(3) Uani 1 1 d . . . . .
H00R H 0.056454 0.079263 0.986844 0.025 Uiso 1 1 calc R U . . .
C00S C 0.30200(11) 0.44325(10) 1.04329(9) 0.0198(3) Uani 1 1 d . . . . .
H00S H 0.271616 0.395682 1.077711 0.024 Uiso 1 1 calc R U . . .
C14 C -0.20013(11) 0.18679(10) 0.69834(9) 0.0204(3) Uani 1 1 d . . . . .
H14 H -0.153344 0.253281 0.748933 0.025 Uiso 1 1 calc R U . . .
C00U C 0.28852(11) 0.34619(10) 0.73428(9) 0.0198(3) Uani 1 1 d . . . . .
H00U H 0.290336 0.326152 0.666832 0.024 Uiso 1 1 calc R U . . .
C00V C 0.40757(11) 0.62908(11) 1.04827(9) 0.0217(3) Uani 1 1 d . . . . .
H00V H 0.447360 0.704399 1.085181 0.026 Uiso 1 1 calc R U . . .
C23 C -0.44176(11) -0.16973(10) 0.55886(10) 0.0225(3) Uani 1 1 d . . . . .
C00X C 0.43138(11) 0.63811(10) 0.87235(9) 0.0207(3) Uani 1 1 d . . . . .
C15 C -0.25695(12) 0.09890(10) 0.72864(9) 0.0218(3) Uani 1 1 d . . . . .
H15 H -0.249534 0.106220 0.797049 0.026 Uiso 1 1 calc R U . . .
C00Z C 0.28727(11) 0.40074(10) 0.93945(9) 0.0180(2) Uani 1 1 d . . . . .
C010 C 0.11056(12) 0.01098(10) 0.80005(9) 0.0214(3) Uani 1 1 d . . . . .
H010 H 0.031689 0.025192 0.770568 0.026 Uiso 1 1 calc R U . . .
C21 C -0.42660(11) -0.12874(11) 0.39025(10) 0.0233(3) Uani 1 1 d . . . . .
H21 H -0.475031 -0.198402 0.345621 0.028 Uiso 1 1 calc R U . . .
C9 C 0.08423(11) 0.32399(11) 0.44355(9) 0.0217(3) Uani 1 1 d . . . . .
H9 H 0.111453 0.378929 0.414394 0.026 Uiso 1 1 calc R U . . .
C013 C 0.31530(11) 0.07519(10) 0.91781(9) 0.0207(3) Uani 1 1 d . . . . .
H013 H 0.376267 0.133072 0.969057 0.025 Uiso 1 1 calc R U . . .
C014 C 0.23476(11) 0.26648(10) 0.77497(9) 0.0203(3) Uani 1 1 d . . . . .
H014 H 0.198689 0.192570 0.732160 0.024 Uiso 1 1 calc R U . . .
C2 C -0.11265(12) 0.59195(11) 0.77778(9) 0.0235(3) Uani 1 1 d . . . . .
H2 H -0.105439 0.662892 0.823756 0.028 Uiso 1 1 calc R U . . .
C016 C 0.34113(12) -0.03065(11) 0.88512(10) 0.0244(3) Uani 1 1 d . . . . .
H016 H 0.420281 -0.044821 0.913906 0.029 Uiso 1 1 calc R U . . .
C20 C -0.37408(12) -0.04433(11) 0.35459(9) 0.0235(3) Uani 1 1 d . . . . .
H20 H -0.387976 -0.058683 0.284547 0.028 Uiso 1 1 calc R U . . .
C018 C -0.14373(12) 0.24215(11) 1.00239(9) 0.0228(3) Uani 1 1 d . . . . .
H018 H -0.216243 0.249317 1.022882 0.027 Uiso 1 1 calc R U . . .
C1 C -0.00746(12) 0.54989(11) 0.76950(9) 0.0232(3) Uani 1 1 d . . . . .
H1 H 0.072300 0.592677 0.809668 0.028 Uiso 1 1 calc R U . . .
C11 C 0.09998(12) 0.15281(11) 0.48594(10) 0.0242(3) Uani 1 1 d . . . . .
H11 H 0.137435 0.089264 0.485000 0.029 Uiso 1 1 calc R U . . .
C01B C 0.01172(11) 0.31098(10) 0.93241(9) 0.0201(3) Uani 1 1 d . . . . .
H01B H 0.044895 0.365958 0.905811 0.024 Uiso 1 1 calc R U . . .
C01C C 0.25255(13) -0.11526(11) 0.81114(10) 0.0255(3) Uani 1 1 d . . . . .
H01C H 0.270608 -0.187518 0.789564 0.031 Uiso 1 1 calc R U . . .
C01D C 0.36028(11) 0.55342(11) 1.09466(9) 0.0214(3) Uani 1 1 d . . . . .
H01D H 0.368951 0.579453 1.164116 0.026 Uiso 1 1 calc R U . . .
C10 C 0.14094(12) 0.23233(11) 0.44340(10) 0.0242(3) Uani 1 1 d . . . . .
H10 H 0.206946 0.224298 0.414487 0.029 Uiso 1 1 calc R U . . .
C01F C 0.41359(12) 0.56209(11) 0.68976(9) 0.0235(3) Uani 1 1 d . . . . .
H01A H 0.434101 0.492419 0.653581 0.028 Uiso 1 1 calc R U . . .
H01E H 0.484384 0.624639 0.704006 0.028 Uiso 1 1 calc R U . . .
C24 C -0.40242(12) -0.12509(11) 0.74558(10) 0.0260(3) Uani 1 1 d . . . . .
H24A H -0.475993 -0.186172 0.727211 0.031 Uiso 1 1 calc R U . . .
H24B H -0.416450 -0.058452 0.791623 0.031 Uiso 1 1 calc R U . . .
C01H C -0.08749(12) 0.15179(11) 1.00988(9) 0.0226(3) Uani 1 1 d . . . . .
H01H H -0.121626 0.096773 1.035973 0.027 Uiso 1 1 calc R U . . .
C01I C 0.13710(13) -0.09472(11) 0.76831(9) 0.0249(3) Uani 1 1 d . . . . .
H01I H 0.076196 -0.152879 0.717297 0.030 Uiso 1 1 calc R U . . .
C01J C 0.29836(13) 0.58447(12) 0.62358(10) 0.0293(3) Uani 1 1 d . . . . .
H01F H 0.312976 0.589960 0.560696 0.044 Uiso 1 1 calc R U . . .
H01G H 0.279759 0.655087 0.657943 0.044 Uiso 1 1 calc R U . . .
H01J H 0.227959 0.522833 0.609384 0.044 Uiso 1 1 calc R U . . .
C25 C -0.28854(13) -0.16140(13) 0.79905(11) 0.0325(3) Uani 1 1 d . . . . .
H25A H -0.275388 -0.228430 0.754289 0.049 Uiso 1 1 calc R U . . .
H25B H -0.300986 -0.178564 0.858963 0.049 Uiso 1 1 calc R U . . .
H25C H -0.215663 -0.100681 0.818440 0.049 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
O001 C00X 1.2228(15) . ?
O1 C23 1.2196(15) . ?
N1 C7 1.4193(15) . ?
N1 C13 1.4278(15) . ?
N1 C5 1.4358(15) . ?
N004 C00C 1.4033(15) . ?
N004 C00X 1.3929(16) . ?
N004 C01F 1.4564(16) . ?
N005 C00A 1.4401(15) . ?
N005 C00I 1.4102(15) . ?
N005 C00O 1.4274(15) . ?
N2 C16 1.4028(15) . ?
N2 C23 1.3940(17) . ?
N2 C24 1.4556(16) . ?
C17 C18 1.3975(16) . ?
C17 C16 1.4073(17) . ?
C17 C22 1.3954(17) . ?
C18 C19 1.4184(17) . ?
C18 C13 1.4349(17) . ?
C7 C12 1.3948(16) . ?
C7 C8 1.4002(16) . ?
C00A C010 1.3875(17) . ?
C00A C013 1.3919(17) . ?
C00B C00C 1.4081(17) . ?
C00B C00E 1.3977(17) . ?
C00B C00Z 1.3949(16) . ?
C00C C00U 1.3618(17) . ?
C16 C15 1.3637(18) . ?
C00E C00V 1.3750(18) . ?
C00E C00X 1.4959(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3825(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3923(17) . ?
C4 C3 1.3889(17) . ?
C13 C14 1.3789(17) . ?
C00I C00R 1.3992(17) . ?
C00I C01B 1.4008(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.3877(18) . ?
C22 C23 1.4985(17) . ?
C22 C21 1.3759(18) . ?
C5 C6 1.3927(17) . ?
C00M H00M 0.9500 . ?
C00M C018 1.3865(18) . ?
C00M C01B 1.3859(18) . ?
C6 H6 0.9500 . ?
C6 C1 1.3857(18) . ?
C00O C00Z 1.4325(17) . ?
C00O C014 1.3808(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3837(17) . ?
C3 H3 0.9500 . ?
C3 C2 1.3897(18) . ?
C00R H00R 0.9500 . ?
C00R C01H 1.3845(18) . ?
C00S H00S 0.9500 . ?
C00S C00Z 1.4200(17) . ?
C00S C01D 1.3828(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.4221(17) . ?
C00U H00U 0.9500 . ?
C00U C014 1.4258(17) . ?
C00V H00V 0.9500 . ?
C00V C01D 1.4153(17) . ?
C15 H15 0.9500 . ?
C010 H010 0.9500 . ?
C010 C01I 1.3907(18) . ?
C21 H21 0.9500 . ?
C21 C20 1.4161(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3891(18) . ?
C013 H013 0.9500 . ?
C013 C016 1.3909(17) . ?
C014 H014 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.3869(18) . ?
C016 H016 0.9500 . ?
C016 C01C 1.3806(19) . ?
C20 H20 0.9500 . ?
C018 H018 0.9500 . ?
C018 C01H 1.3852(18) . ?
C1 H1 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.3847(18) . ?
C01B H01B 0.9500 . ?
C01C H01C 0.9500 . ?
C01C C01I 1.3881(19) . ?
C01D H01D 0.9500 . ?
C10 H10 0.9500 . ?
C01F H01A 0.9900 . ?
C01F H01E 0.9900 . ?
C01F C01J 1.5178(18) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5168(19) . ?
C01H H01H 0.9500 . ?
C01I H01I 0.9500 . ?
C01J H01F 0.9800 . ?
C01J H01G 0.9800 . ?
C01J H01J 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C7 N1 C13 118.66(9) . . ?
C7 N1 C5 116.92(10) . . ?
C13 N1 C5 115.92(9) . . ?
C00C N004 C01F 124.90(11) . . ?
C00X N004 C00C 110.76(10) . . ?
C00X N004 C01F 124.22(10) . . ?
C00I N005 C00A 119.44(10) . . ?
C00I N005 C00O 120.04(9) . . ?
C00O N005 C00A 116.11(9) . . ?
C16 N2 C24 124.56(11) . . ?
C23 N2 C16 110.84(10) . . ?
C23 N2 C24 124.60(11) . . ?
C18 C17 C16 124.84(11) . . ?
C22 C17 C18 125.10(11) . . ?
C22 C17 C16 110.06(11) . . ?
C17 C18 C19 114.89(11) . . ?
C17 C18 C13 115.37(10) . . ?
C19 C18 C13 129.74(11) . . ?
C12 C7 N1 122.24(10) . . ?
C12 C7 C8 118.74(11) . . ?
C8 C7 N1 119.02(10) . . ?
C010 C00A N005 121.22(11) . . ?
C010 C00A C013 120.15(11) . . ?
C013 C00A N005 118.62(11) . . ?
C00E C00B C00C 110.29(11) . . ?
C00Z C00B C00C 124.76(11) . . ?
C00Z C00B C00E 124.89(11) . . ?
N004 C00C C00B 107.09(11) . . ?
C00U C00C N004 133.33(11) . . ?
C00U C00C C00B 119.55(11) . . ?
N2 C16 C17 107.28(11) . . ?
C15 C16 N2 133.23(11) . . ?
C15 C16 C17 119.48(11) . . ?
C00B C00E C00X 105.98(10) . . ?
C00V C00E C00B 119.39(11) . . ?
C00V C00E C00X 134.60(12) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.53(11) . . ?
C20 C19 H19 119.7 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.55(11) . . ?
N1 C13 C18 120.36(10) . . ?
C14 C13 N1 120.66(11) . . ?
C14 C13 C18 118.98(11) . . ?
C00R C00I N005 119.97(10) . . ?
C00R C00I C01B 118.19(11) . . ?
C01B C00I N005 121.82(11) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.05(11) . . ?
C11 C12 H12 120.0 . . ?
C17 C22 C23 106.35(11) . . ?
C21 C22 C17 119.18(11) . . ?
C21 C22 C23 134.47(12) . . ?
C4 C5 N1 119.19(11) . . ?
C4 C5 C6 119.78(11) . . ?
C6 C5 N1 121.01(11) . . ?
C018 C00M H00M 119.5 . . ?
C01B C00M H00M 119.5 . . ?
C01B C00M C018 120.95(11) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.05(11) . . ?
C1 C6 H6 120.0 . . ?
N005 C00O C00Z 120.02(11) . . ?
C014 C00O N005 120.75(11) . . ?
C014 C00O C00Z 119.23(11) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.64(11) . . ?
C9 C8 H8 119.7 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.88(12) . . ?
C2 C3 H3 119.6 . . ?
C00I C00R H00R 119.6 . . ?
C01H C00R C00I 120.76(11) . . ?
C01H C00R H00R 119.6 . . ?
C00Z C00S H00S 119.8 . . ?
C01D C00S H00S 119.8 . . ?
C01D C00S C00Z 120.46(11) . . ?
C13 C14 H14 117.8 . . ?
C13 C14 C15 124.33(12) . . ?
C15 C14 H14 117.8 . . ?
C00C C00U H00U 121.4 . . ?
C00C C00U C014 117.11(11) . . ?
C014 C00U H00U 121.4 . . ?
C00E C00V H00V 121.3 . . ?
C00E C00V C01D 117.37(12) . . ?
C01D C00V H00V 121.3 . . ?
O1 C23 N2 124.98(12) . . ?
O1 C23 C22 129.55(13) . . ?
N2 C23 C22 105.46(10) . . ?
O001 C00X N004 124.56(11) . . ?
O001 C00X C00E 129.60(12) . . ?
N004 C00X C00E 105.83(10) . . ?
C16 C15 C14 116.99(11) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
C00B C00Z C00O 115.42(11) . . ?
C00B C00Z C00S 115.02(11) . . ?
C00S C00Z C00O 129.55(11) . . ?
C00A C010 H010 120.1 . . ?
C00A C010 C01I 119.89(12) . . ?
C01I C010 H010 120.1 . . ?
C22 C21 H21 121.3 . . ?
C22 C21 C20 117.47(12) . . ?
C20 C21 H21 121.3 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.39(11) . . ?
C10 C9 H9 119.8 . . ?
C00A C013 H013 120.3 . . ?
C016 C013 C00A 119.50(12) . . ?
C016 C013 H013 120.3 . . ?
C00O C014 C00U 123.85(12) . . ?
C00O C014 H014 118.1 . . ?
C00U C014 H014 118.1 . . ?
C3 C2 H2 120.4 . . ?
C1 C2 C3 119.15(12) . . ?
C1 C2 H2 120.4 . . ?
C013 C016 H016 119.8 . . ?
C01C C016 C013 120.47(12) . . ?
C01C C016 H016 119.8 . . ?
C19 C20 C21 122.82(12) . . ?
C19 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
C00M C018 H018 120.5 . . ?
C01H C018 C00M 118.95(12) . . ?
C01H C018 H018 120.5 . . ?
C6 C1 C2 120.59(12) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.04(11) . . ?
C10 C11 H11 119.5 . . ?
C00I C01B H01B 119.8 . . ?
C00M C01B C00I 120.40(11) . . ?
C00M C01B H01B 119.8 . . ?
C016 C01C H01C 120.0 . . ?
C016 C01C C01I 119.98(12) . . ?
C01I C01C H01C 120.0 . . ?
C00S C01D C00V 122.87(12) . . ?
C00S C01D H01D 118.6 . . ?
C00V C01D H01D 118.6 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.12(12) . . ?
C11 C10 H10 120.4 . . ?
N004 C01F H01A 109.2 . . ?
N004 C01F H01E 109.2 . . ?
N004 C01F C01J 112.20(11) . . ?
H01A C01F H01E 107.9 . . ?
C01J C01F H01A 109.2 . . ?
C01J C01F H01E 109.2 . . ?
N2 C24 H24A 109.2 . . ?
N2 C24 H24B 109.2 . . ?
N2 C24 C25 112.24(11) . . ?
H24A C24 H24B 107.9 . . ?
C25 C24 H24A 109.2 . . ?
C25 C24 H24B 109.2 . . ?
C00R C01H C018 120.71(12) . . ?
C00R C01H H01H 119.6 . . ?
C018 C01H H01H 119.6 . . ?
C010 C01I H01I 120.0 . . ?
C01C C01I C010 120.01(12) . . ?
C01C C01I H01I 120.0 . . ?
C01F C01J H01F 109.5 . . ?
C01F C01J H01G 109.5 . . ?
C01F C01J H01J 109.5 . . ?
H01F C01J H01G 109.5 . . ?
H01F C01J H01J 109.5 . . ?
H01G C01J H01J 109.5 . . ?
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 . . ?

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 C12 C11 -178.67(11) . . . . ?
N1 C7 C8 C9 177.78(11) . . . . ?
N1 C13 C14 C15 -179.37(11) . . . . ?
N1 C5 C6 C1 -177.97(11) . . . . ?
N004 C00C C00U C014 179.47(12) . . . . ?
N005 C00A C010 C01I 179.00(11) . . . . ?
N005 C00A C013 C016 -178.68(11) . . . . ?
N005 C00I C00R C01H -179.72(11) . . . . ?
N005 C00I C01B C00M -179.11(11) . . . . ?
N005 C00O C00Z C00B -177.49(10) . . . . ?
N005 C00O C00Z C00S 3.53(18) . . . . ?
N005 C00O C014 C00U 179.44(10) . . . . ?
N2 C16 C15 C14 -179.92(12) . . . . ?
C17 C18 C19 C20 -0.50(16) . . . . ?
C17 C18 C13 N1 178.61(10) . . . . ?
C17 C18 C13 C14 -1.24(16) . . . . ?
C17 C16 C15 C14 -1.02(17) . . . . ?
C17 C22 C23 O1 -177.90(12) . . . . ?
C17 C22 C23 N2 0.82(12) . . . . ?
C17 C22 C21 C20 -0.27(17) . . . . ?
C18 C17 C16 N2 179.37(10) . . . . ?
C18 C17 C16 C15 0.21(18) . . . . ?
C18 C17 C22 C23 -179.85(10) . . . . ?
C18 C17 C22 C21 0.34(18) . . . . ?
C18 C19 C20 C21 0.59(18) . . . . ?
C18 C13 C14 C15 0.48(18) . . . . ?
C7 N1 C13 C18 -63.34(14) . . . . ?
C7 N1 C13 C14 116.50(12) . . . . ?
C7 N1 C5 C4 147.44(11) . . . . ?
C7 N1 C5 C6 -34.38(15) . . . . ?
C7 C12 C11 C10 0.74(19) . . . . ?
C7 C8 C9 C10 1.12(18) . . . . ?
C00A N005 C00I C00R 28.72(16) . . . . ?
C00A N005 C00I C01B -153.03(11) . . . . ?
C00A N005 C00O C00Z -138.27(11) . . . . ?
C00A N005 C00O C014 41.45(15) . . . . ?
C00A C010 C01I C01C -0.27(18) . . . . ?
C00A C013 C016 C01C -0.44(18) . . . . ?
C00B C00C C00U C014 1.63(17) . . . . ?
C00B C00E C00V C01D -0.50(17) . . . . ?
C00B C00E C00X O001 176.95(12) . . . . ?
C00B C00E C00X N004 -2.27(12) . . . . ?
C00C N004 C00X O001 -177.25(11) . . . . ?
C00C N004 C00X C00E 2.02(12) . . . . ?
C00C N004 C01F C01J 81.47(14) . . . . ?
C00C C00B C00E C00V -176.55(11) . . . . ?
C00C C00B C00E C00X 1.74(13) . . . . ?
C00C C00B C00Z C00O -2.73(17) . . . . ?
C00C C00B C00Z C00S 176.41(11) . . . . ?
C00C C00U C014 C00O -1.47(18) . . . . ?
C16 N2 C23 O1 177.99(11) . . . . ?
C16 N2 C23 C22 -0.82(13) . . . . ?
C16 N2 C24 C25 -79.44(15) . . . . ?
C16 C17 C18 C19 -179.15(11) . . . . ?
C16 C17 C18 C13 0.95(16) . . . . ?
C16 C17 C22 C23 -0.54(13) . . . . ?
C16 C17 C22 C21 179.65(10) . . . . ?
C00E C00B C00C N004 -0.55(13) . . . . ?
C00E C00B C00C C00U 177.81(10) . . . . ?
C00E C00B C00Z C00O -179.66(11) . . . . ?
C00E C00B C00Z C00S -0.52(17) . . . . ?
C00E C00V C01D C00S 0.08(17) . . . . ?
C19 C18 C13 N1 -1.28(18) . . . . ?
C19 C18 C13 C14 178.88(11) . . . . ?
C4 C5 C6 C1 0.19(17) . . . . ?
C4 C3 C2 C1 0.12(18) . . . . ?
C13 N1 C7 C12 -15.79(16) . . . . ?
C13 N1 C7 C8 164.99(10) . . . . ?
C13 N1 C5 C4 -64.90(14) . . . . ?
C13 N1 C5 C6 113.27(12) . . . . ?
C13 C18 C19 C20 179.38(11) . . . . ?
C13 C14 C15 C16 0.70(18) . . . . ?
C00I N005 C00A C010 53.19(15) . . . . ?
C00I N005 C00A C013 -128.12(12) . . . . ?
C00I N005 C00O C00Z 65.43(15) . . . . ?
C00I N005 C00O C014 -114.85(13) . . . . ?
C00I C00R C01H C018 -1.46(19) . . . . ?
C12 C7 C8 C9 -1.47(18) . . . . ?
C12 C11 C10 C9 -1.11(19) . . . . ?
C22 C17 C18 C19 0.06(17) . . . . ?
C22 C17 C18 C13 -179.84(11) . . . . ?
C22 C17 C16 N2 0.06(13) . . . . ?
C22 C17 C16 C15 -179.10(11) . . . . ?
C22 C21 C20 C19 -0.18(18) . . . . ?
C5 N1 C7 C12 130.95(12) . . . . ?
C5 N1 C7 C8 -48.27(15) . . . . ?
C5 N1 C13 C18 149.59(10) . . . . ?
C5 N1 C13 C14 -30.57(15) . . . . ?
C5 C4 C3 C2 0.47(17) . . . . ?
C5 C6 C1 C2 0.41(18) . . . . ?
C00M C018 C01H C00R -0.24(18) . . . . ?
C00O N005 C00A C010 -103.25(13) . . . . ?
C00O N005 C00A C013 75.43(14) . . . . ?
C00O N005 C00I C00R -175.77(11) . . . . ?
C00O N005 C00I C01B 2.48(17) . . . . ?
C8 C7 C12 C11 0.55(18) . . . . ?
C8 C9 C10 C11 0.18(18) . . . . ?
C3 C4 C5 N1 177.57(10) . . . . ?
C3 C4 C5 C6 -0.63(17) . . . . ?
C3 C2 C1 C6 -0.56(18) . . . . ?
C00R C00I C01B C00M -0.83(17) . . . . ?
C00V C00E C00X O001 -5.1(2) . . . . ?
C00V C00E C00X N004 175.64(13) . . . . ?
C23 N2 C16 C17 0.50(13) . . . . ?
C23 N2 C16 C15 179.50(13) . . . . ?
C23 N2 C24 C25 100.03(14) . . . . ?
C23 C22 C21 C20 179.99(12) . . . . ?
C00X N004 C00C C00B -1.00(13) . . . . ?
C00X N004 C00C C00U -179.03(12) . . . . ?
C00X N004 C01F C01J -94.23(14) . . . . ?
C00X C00E C00V C01D -178.19(12) . . . . ?
C00Z C00B C00C N004 -177.87(10) . . . . ?
C00Z C00B C00C C00U 0.49(18) . . . . ?
C00Z C00B C00E C00V 0.76(18) . . . . ?
C00Z C00B C00E C00X 179.05(11) . . . . ?
C00Z C00O C014 C00U -0.84(18) . . . . ?
C00Z C00S C01D C00V 0.14(18) . . . . ?
C010 C00A C013 C016 0.02(18) . . . . ?
C21 C22 C23 O1 1.9(2) . . . . ?
C21 C22 C23 N2 -179.41(13) . . . . ?
C013 C00A C010 C01I 0.33(18) . . . . ?
C013 C016 C01C C01I 0.50(19) . . . . ?
C014 C00O C00Z C00B 2.79(16) . . . . ?
C014 C00O C00Z C00S -176.19(12) . . . . ?
C016 C01C C01I C010 -0.14(19) . . . . ?
C018 C00M C01B C00I -0.85(18) . . . . ?
C01B C00I C00R C01H 1.97(18) . . . . ?
C01B C00M C018 C01H 1.39(19) . . . . ?
C01D C00S C00Z C00B 0.07(16) . . . . ?
C01D C00S C00Z C00O 179.06(11) . . . . ?
C01F N004 C00C C00B -177.20(10) . . . . ?
C01F N004 C00C C00U 4.8(2) . . . . ?
C01F N004 C00X O001 -1.02(18) . . . . ?
C01F N004 C00X C00E 178.25(10) . . . . ?
C24 N2 C16 C17 -179.96(10) . . . . ?
C24 N2 C16 C15 -1.0(2) . . . . ?
C24 N2 C23 O1 -1.55(19) . . . . ?
C24 N2 C23 C22 179.65(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
