# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_abh-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2271792'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2023-06-23 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H17 Cl N3 O2'
_chemical_formula_weight         438.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   30.8340(15)
_cell_length_b                   7.8320(2)
_cell_length_c                   22.5177(11)
_cell_angle_alpha                90
_cell_angle_beta                 132.054(8)
_cell_angle_gamma                90
_cell_volume                     4037.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    261(2)
_cell_measurement_reflns_used    9232
_cell_measurement_theta_min      2.8430
_cell_measurement_theta_max      76.3560

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.925
_shelx_estimated_absorpt_T_min   0.578
_shelx_estimated_absorpt_T_max   0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.13661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      261(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21560
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.862
_diffrn_reflns_theta_max         78.565
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4262
_reflns_number_gt                3547
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1824P)²+1.9874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4262
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.2661
_refine_ls_wR_factor_gt          0.2537
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.32077(11) 0.4252(3) 0.57369(14) 0.0427(5) Uani 1 1 d . . . . .
C2 C 0.29573(11) 0.3743(3) 0.49611(14) 0.0449(5) Uani 1 1 d . . . . .
C3 C 0.23938(11) 0.4268(3) 0.42829(14) 0.0450(5) Uani 1 1 d . . . . .
C4 C 0.20735(11) 0.5256(3) 0.43990(15) 0.0451(5) Uani 1 1 d . . . . .
C5 C 0.23162(10) 0.5789(3) 0.51768(14) 0.0427(5) Uani 1 1 d . . . . .
C6 C 0.28958(10) 0.5297(3) 0.58519(14) 0.0426(5) Uani 1 1 d . . . . .
C7 C 0.38188(11) 0.4715(3) 0.70465(15) 0.0472(6) Uani 1 1 d . . . . .
C8 C 0.32978(11) 0.5615(3) 0.67055(14) 0.0455(5) Uani 1 1 d . . . . .
C9 C 0.32863(12) 0.6564(4) 0.72158(17) 0.0562(7) Uani 1 1 d . . . . .
H9 H 0.295438 0.718566 0.701089 0.067 Uiso 1 1 calc R U . . .
C10 C 0.37664(13) 0.6585(5) 0.80259(18) 0.0679(9) Uani 1 1 d . . . . .
H10 H 0.375282 0.721426 0.836348 0.081 Uiso 1 1 calc R U . . .
C11 C 0.42736(13) 0.5676(5) 0.83486(18) 0.0663(8) Uani 1 1 d . . . . .
H11 H 0.459080 0.570304 0.889733 0.080 Uiso 1 1 calc R U . . .
C12 C 0.43093(12) 0.4741(4) 0.78636(17) 0.0580(7) Uani 1 1 d . . . . .
H12 H 0.464755 0.415077 0.807350 0.070 Uiso 1 1 calc R U . . .
C13 C 0.27877(12) 0.2613(3) 0.39072(15) 0.0502(6) Uani 1 1 d . . . . .
C14 C 0.28232(14) 0.1688(4) 0.34199(18) 0.0581(7) Uani 1 1 d . . . . .
H14 H 0.315515 0.105807 0.363118 0.070 Uiso 1 1 calc R U . . .
C15 C 0.23458(16) 0.1731(4) 0.26036(19) 0.0649(8) Uani 1 1 d . . . . .
H15 H 0.235509 0.110754 0.226067 0.078 Uiso 1 1 calc R U . . .
C16 C 0.18508(16) 0.2696(4) 0.22881(18) 0.0663(8) Uani 1 1 d . . . . .
H16 H 0.154022 0.272168 0.173716 0.080 Uiso 1 1 calc R U . . .
C17 C 0.18121(14) 0.3610(4) 0.27737(17) 0.0576(7) Uani 1 1 d . . . . .
H17 H 0.148009 0.424728 0.255584 0.069 Uiso 1 1 calc R U . . .
C18 C 0.22820(12) 0.3561(3) 0.36007(15) 0.0486(6) Uani 1 1 d . . . . .
C19 C 0.13731(11) 0.6744(3) 0.42138(16) 0.0504(6) Uani 1 1 d . . . . .
C20 C 0.08521(12) 0.7600(4) 0.38666(19) 0.0625(8) Uani 1 1 d . . . . .
H20 H 0.053994 0.760254 0.331599 0.075 Uiso 1 1 calc R U . . .
C21 C 0.08217(13) 0.8435(4) 0.4373(2) 0.0658(8) Uani 1 1 d . . . . .
H21 H 0.048498 0.904218 0.415790 0.079 Uiso 1 1 calc R U . . .
C22 C 0.12811(14) 0.8401(4) 0.5201(2) 0.0635(8) Uani 1 1 d . . . . .
H22 H 0.124167 0.895205 0.552834 0.076 Uiso 1 1 calc R U . . .
C23 C 0.17956(12) 0.7553(4) 0.55392(17) 0.0545(6) Uani 1 1 d . . . . .
H23 H 0.210029 0.753407 0.609176 0.065 Uiso 1 1 calc R U . . .
C24 C 0.18545(11) 0.6732(3) 0.50498(15) 0.0452(5) Uani 1 1 d . . . . .
C25 C 0.48155(13) 0.1053(4) 0.64455(17) 0.0559(6) Uani 1 1 d . . . . .
C26 C 0.49808(17) 0.0629(6) 0.5961(2) 0.0763(10) Uani 1 1 d . . . . .
H26A H 0.494606 -0.059328 0.586988 0.092 Uiso 1 1 calc R U . . .
H26B H 0.538584 0.094053 0.626782 0.092 Uiso 1 1 calc R U . . .
N1 N 0.37469(9) 0.3879(3) 0.64485(13) 0.0472(5) Uani 1 1 d . . . . .
H1 H 0.400078 0.322900 0.651386 0.057 Uiso 1 1 calc R U . . .
N2 N 0.31914(10) 0.2754(3) 0.47375(13) 0.0489(5) Uani 1 1 d . . . . .
H2 H 0.353215 0.229207 0.505692 0.059 Uiso 1 1 calc R U . . .
N3 N 0.15147(10) 0.5824(3) 0.38420(13) 0.0518(5) Uani 1 1 d . . . . .
H3 H 0.128499 0.563874 0.333607 0.062 Uiso 1 1 calc R U . . .
Cl1 Cl 0.45442(7) 0.1683(3) 0.50390(7) 0.1344(7) Uani 1 1 d . . . . .
O5 O 0.43840(10) 0.1863(3) 0.61742(14) 0.0654(6) Uani 1 1 d . . . . .
O4 O 0.51868(10) 0.0453(3) 0.71543(13) 0.0684(6) Uani 1 1 d . . . A -1
H4 H 0.533888 0.124014 0.747737 0.103 Uiso 1 1 calc DR U . A -1


_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 N1 1.359(3) . ?
C1 C6 1.413(4) . ?
C1 C2 1.414(3) . ?
C2 N2 1.365(3) . ?
C2 C3 1.402(4) . ?
C3 C4 1.410(4) . ?
C3 C18 1.441(3) . ?
C4 N3 1.358(3) . ?
C4 C5 1.430(3) . ?
C5 C6 1.419(3) . ?
C5 C24 1.452(4) . ?
C6 C8 1.450(3) . ?
C7 N1 1.375(3) . ?
C7 C12 1.395(4) . ?
C7 C8 1.419(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.399(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.379(4) . ?
C13 N2 1.393(3) . ?
C13 C18 1.420(4) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.398(4) . ?
C17 H17 0.9300 . ?
C19 N3 1.379(4) . ?
C19 C20 1.400(4) . ?
C19 C24 1.415(3) . ?
C20 C21 1.371(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(4) . ?
C23 H23 0.9300 . ?
C25 O5 1.207(4) . ?
C25 O4 1.277(4) . ?
C25 C26 1.517(4) . ?
C26 Cl1 1.750(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?
N3 H3 0.8600 . ?
O4 H4 0.8200 . ?

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
N1 C1 C6 110.7(2) . . ?
N1 C1 C2 128.4(2) . . ?
C6 C1 C2 120.9(2) . . ?
N2 C2 C3 109.9(2) . . ?
N2 C2 C1 129.0(2) . . ?
C3 C2 C1 121.1(2) . . ?
C2 C3 C4 118.0(2) . . ?
C2 C3 C18 106.6(2) . . ?
C4 C3 C18 135.4(2) . . ?
N3 C4 C3 128.4(2) . . ?
N3 C4 C5 109.6(2) . . ?
C3 C4 C5 122.0(2) . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 C24 135.6(2) . . ?
C4 C5 C24 105.5(2) . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C8 105.1(2) . . ?
C5 C6 C8 135.9(2) . . ?
N1 C7 C12 128.3(2) . . ?
N1 C7 C8 109.0(2) . . ?
C12 C7 C8 122.7(2) . . ?
C9 C8 C7 117.7(2) . . ?
C9 C8 C6 135.7(2) . . ?
C7 C8 C6 106.5(2) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 117.5(3) . . ?
C11 C12 H12 121.3 . . ?
C7 C12 H12 121.3 . . ?
C14 C13 N2 129.3(3) . . ?
C14 C13 C18 122.3(3) . . ?
N2 C13 C18 108.3(2) . . ?
C13 C14 C15 117.5(3) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 118.6(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C13 118.9(2) . . ?
C17 C18 C3 134.7(3) . . ?
C13 C18 C3 106.4(2) . . ?
N3 C19 C20 128.5(3) . . ?
N3 C19 C24 109.1(2) . . ?
C20 C19 C24 122.3(3) . . ?
C21 C20 C19 117.1(3) . . ?
C21 C20 H20 121.4 . . ?
C19 C20 H20 121.4 . . ?
C20 C21 C22 121.9(3) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 118.3(2) . . ?
C23 C24 C5 135.3(2) . . ?
C19 C24 C5 106.4(2) . . ?
O5 C25 O4 126.0(3) . . ?
O5 C25 C26 122.6(3) . . ?
O4 C25 C26 111.5(3) . . ?
C25 C26 Cl1 112.8(2) . . ?
C25 C26 H26A 109.0 . . ?
Cl1 C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
Cl1 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C1 N1 C7 108.7(2) . . ?
C1 N1 H1 125.7 . . ?
C7 N1 H1 125.7 . . ?
C2 N2 C13 108.8(2) . . ?
C2 N2 H2 125.6 . . ?
C13 N2 H2 125.6 . . ?
C4 N3 C19 109.4(2) . . ?
C4 N3 H3 125.3 . . ?
C19 N3 H3 125.3 . . ?
C25 O4 H4 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 0.5(4) . . . . ?
C6 C1 C2 N2 179.8(2) . . . . ?
N1 C1 C2 C3 -178.9(2) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
N2 C2 C3 C4 177.7(2) . . . . ?
C1 C2 C3 C4 -2.8(3) . . . . ?
N2 C2 C3 C18 -0.7(3) . . . . ?
C1 C2 C3 C18 178.8(2) . . . . ?
C2 C3 C4 N3 -176.1(2) . . . . ?
C18 C3 C4 N3 1.7(5) . . . . ?
C2 C3 C4 C5 2.8(3) . . . . ?
C18 C3 C4 C5 -179.4(3) . . . . ?
N3 C4 C5 C6 178.6(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
N3 C4 C5 C24 0.3(3) . . . . ?
C3 C4 C5 C24 -178.8(2) . . . . ?
N1 C1 C6 C5 -178.5(2) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
N1 C1 C6 C8 2.3(3) . . . . ?
C2 C1 C6 C8 -177.1(2) . . . . ?
C4 C5 C6 C1 -2.0(3) . . . . ?
C24 C5 C6 C1 175.7(2) . . . . ?
C4 C5 C6 C8 176.8(2) . . . . ?
C24 C5 C6 C8 -5.5(5) . . . . ?
N1 C7 C8 C9 -179.2(2) . . . . ?
C12 C7 C8 C9 0.5(4) . . . . ?
N1 C7 C8 C6 -0.4(3) . . . . ?
C12 C7 C8 C6 179.3(2) . . . . ?
C1 C6 C8 C9 177.4(3) . . . . ?
C5 C6 C8 C9 -1.5(5) . . . . ?
C1 C6 C8 C7 -1.1(3) . . . . ?
C5 C6 C8 C7 180.0(3) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C6 C8 C9 C10 -179.5(3) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 C7 -1.1(5) . . . . ?
N1 C7 C12 C11 -179.7(3) . . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
N2 C13 C14 C15 178.0(3) . . . . ?
C18 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C17 -1.4(5) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C13 1.9(4) . . . . ?
C16 C17 C18 C3 -177.3(3) . . . . ?
C14 C13 C18 C17 -2.5(4) . . . . ?
N2 C13 C18 C17 -180.0(2) . . . . ?
C14 C13 C18 C3 176.9(2) . . . . ?
N2 C13 C18 C3 -0.6(3) . . . . ?
C2 C3 C18 C17 180.0(3) . . . . ?
C4 C3 C18 C17 2.0(5) . . . . ?
C2 C3 C18 C13 0.8(3) . . . . ?
C4 C3 C18 C13 -177.2(3) . . . . ?
N3 C19 C20 C21 -179.7(3) . . . . ?
C24 C19 C20 C21 -0.3(4) . . . . ?
C19 C20 C21 C22 -1.8(5) . . . . ?
C20 C21 C22 C23 2.0(5) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C19 -2.1(4) . . . . ?
C22 C23 C24 C5 177.8(3) . . . . ?
N3 C19 C24 C23 -178.2(2) . . . . ?
C20 C19 C24 C23 2.3(4) . . . . ?
N3 C19 C24 C5 1.9(3) . . . . ?
C20 C19 C24 C5 -177.6(2) . . . . ?
C6 C5 C24 C23 0.9(5) . . . . ?
C4 C5 C24 C23 178.8(3) . . . . ?
C6 C5 C24 C19 -179.2(3) . . . . ?
C4 C5 C24 C19 -1.3(3) . . . . ?
O5 C25 C26 Cl1 8.5(5) . . . . ?
O4 C25 C26 Cl1 -171.3(3) . . . . ?
C6 C1 N1 C7 -2.6(3) . . . . ?
C2 C1 N1 C7 176.7(2) . . . . ?
C12 C7 N1 C1 -177.9(3) . . . . ?
C8 C7 N1 C1 1.8(3) . . . . ?
C3 C2 N2 C13 0.3(3) . . . . ?
C1 C2 N2 C13 -179.2(2) . . . . ?
C14 C13 N2 C2 -177.0(3) . . . . ?
C18 C13 N2 C2 0.2(3) . . . . ?
C3 C4 N3 C19 179.9(2) . . . . ?
C5 C4 N3 C19 0.9(3) . . . . ?
C20 C19 N3 C4 177.7(3) . . . . ?
C24 C19 N3 C4 -1.7(3) . . . . ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_abh-4_auto
_database_code_depnum_ccdc_archive 'CCDC 2271798'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2023-06-23 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H27 N3'
_chemical_formula_weight         573.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.36721(18)
_cell_length_b                   9.18575(9)
_cell_length_c                   19.55340(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.7495(9)
_cell_angle_gamma                90
_cell_volume                     2938.39(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    236(2)
_cell_measurement_reflns_used    22049
_cell_measurement_theta_min      5.2980
_cell_measurement_theta_max      77.8190

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.587
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8344
_exptl_absorpt_correction_T_max  0.9276
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      236(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35966
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.470
_diffrn_reflns_theta_max         78.058
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6265
_reflns_number_gt                5570
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+0.4809P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6265
_refine_ls_number_parameters     407
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.22794(6) 0.23806(12) 0.98631(5) 0.0365(2) Uani 1 1 d . . . . .
C2 C 0.20623(6) 0.14107(12) 0.93322(5) 0.0356(2) Uani 1 1 d . . . . .
C3 C 0.12200(6) 0.12099(11) 0.91773(5) 0.0358(2) Uani 1 1 d . . . . .
C4 C 0.06119(6) 0.17744(12) 0.95939(5) 0.0369(2) Uani 1 1 d . . . . .
C5 C 0.08468(6) 0.27569(12) 1.01277(5) 0.0375(2) Uani 1 1 d . . . . .
C6 C 0.16768(7) 0.31253(12) 1.02219(5) 0.0384(2) Uani 1 1 d . . . . .
C7 C 0.34521(7) 0.14022(12) 0.94983(5) 0.0386(2) Uani 1 1 d . . . . .
C8 C 0.28161(6) 0.07646(12) 0.91009(5) 0.0367(2) Uani 1 1 d . . . . .
C9 C 0.30196(7) -0.03201(13) 0.86331(6) 0.0428(3) Uani 1 1 d . . . . .
H9 H 0.260820 -0.078153 0.836634 0.051 Uiso 1 1 calc R U . . .
C10 C 0.38293(8) -0.07090(14) 0.85655(7) 0.0493(3) Uani 1 1 d . . . . .
H10 H 0.396551 -0.142359 0.824430 0.059 Uiso 1 1 calc R U . . .
C11 C 0.44451(7) -0.00610(15) 0.89647(7) 0.0519(3) Uani 1 1 d . . . . .
H11 H 0.499094 -0.034576 0.891037 0.062 Uiso 1 1 calc R U . . .
C12 C 0.42671(7) 0.09930(15) 0.94391(6) 0.0475(3) Uani 1 1 d . . . . .
H12 H 0.468211 0.142251 0.971398 0.057 Uiso 1 1 calc R U . . .
C13 C 0.09931(8) 0.44798(13) 1.09757(6) 0.0442(3) Uani 1 1 d . . . . .
C14 C 0.04119(7) 0.36080(12) 1.06248(6) 0.0406(2) Uani 1 1 d . . . . .
C15 C -0.04052(8) 0.37563(15) 1.08049(7) 0.0525(3) Uani 1 1 d . . . . .
H15 H -0.081025 0.318312 1.058537 0.063 Uiso 1 1 calc DR U . . .
C16 C -0.06190(9) 0.47338(16) 1.13002(8) 0.0593(3) Uani 1 1 d . . . . .
H16 H -0.116952 0.481695 1.141823 0.071 Uiso 1 1 calc R U . . .
C17 C -0.00355(10) 0.55977(16) 1.16276(8) 0.0604(4) Uani 1 1 d . . . . .
H17 H -0.019459 0.626285 1.196381 0.072 Uiso 1 1 calc R U . . .
C18 C 0.07768(9) 0.54939(16) 1.14664(7) 0.0564(3) Uani 1 1 d . . . . .
H18 H 0.117312 0.609181 1.168212 0.068 Uiso 1 1 calc R U . . .
C19 C 0.00155(7) 0.03732(13) 0.87442(6) 0.0410(2) Uani 1 1 d . . . . .
C20 C -0.05891(8) -0.02615(16) 0.83254(7) 0.0525(3) Uani 1 1 d . . . . .
H20 H -0.045570 -0.079689 0.793458 0.063 Uiso 1 1 calc R U . . .
C21 C -0.13882(8) -0.00760(18) 0.85047(7) 0.0588(4) Uani 1 1 d . . . . .
H21 H -0.180995 -0.047646 0.822707 0.071 Uiso 1 1 calc R U . . .
C22 C -0.15819(8) 0.06904(16) 0.90870(8) 0.0575(3) Uani 1 1 d . . . . .
H22 H -0.213186 0.077931 0.920575 0.069 Uiso 1 1 calc R U . . .
C23 C -0.09819(7) 0.13237(15) 0.94944(7) 0.0512(3) Uani 1 1 d . . . . .
H23 H -0.112309 0.183559 0.988995 0.061 Uiso 1 1 calc DR U . . .
C24 C -0.01624(7) 0.12077(12) 0.93215(6) 0.0395(2) Uani 1 1 d . . . . .
C25 C 0.35819(7) 0.27678(13) 1.05689(6) 0.0419(3) Uani 1 1 d . . . . .
C26 C 0.42668(8) 0.36392(16) 1.05367(8) 0.0572(3) Uani 1 1 d . . . . .
H26 H 0.441760 0.404504 1.011762 0.069 Uiso 1 1 calc R U . . .
C27 C 0.47292(10) 0.3909(2) 1.11271(11) 0.0781(5) Uani 1 1 d . . . . .
H27 H 0.520090 0.448983 1.110682 0.094 Uiso 1 1 calc R U . . .
C28 C 0.45085(12) 0.3345(2) 1.17341(10) 0.0881(7) Uani 1 1 d . . . . .
H28 H 0.482298 0.354560 1.213327 0.106 Uiso 1 1 calc R U . . .
C29 C 0.38245(13) 0.2480(2) 1.17677(8) 0.0830(6) Uani 1 1 d . . . . .
H29 H 0.367309 0.209315 1.219050 0.100 Uiso 1 1 calc R U . . .
C30 C 0.33564(9) 0.21736(17) 1.11803(7) 0.0573(3) Uani 1 1 d . . . . .
H30 H 0.289374 0.157071 1.120061 0.069 Uiso 1 1 calc R U . . .
C31 C 0.23980(7) 0.52747(13) 1.07469(7) 0.0462(3) Uani 1 1 d . . . . .
C32 C 0.26294(9) 0.59225(15) 1.01438(8) 0.0562(3) Uani 1 1 d . . . . .
H32 H 0.238695 0.563177 0.972371 0.067 Uiso 1 1 calc R U . . .
C33 C 0.32228(11) 0.70063(18) 1.01634(11) 0.0775(5) Uani 1 1 d . . . . .
H33 H 0.338682 0.744263 0.975498 0.093 Uiso 1 1 calc R U . . .
C34 C 0.35708(11) 0.7442(2) 1.07807(13) 0.0869(6) Uani 1 1 d . . . . .
H34 H 0.396927 0.817894 1.079320 0.104 Uiso 1 1 calc R U . . .
C35 C 0.33358(10) 0.6798(2) 1.13782(11) 0.0788(5) Uani 1 1 d . . . . .
H35 H 0.357256 0.710299 1.179828 0.095 Uiso 1 1 calc R U . . .
C36 C 0.27537(9) 0.57071(17) 1.13662(8) 0.0599(3) Uani 1 1 d . . . . .
H36 H 0.260025 0.526127 1.177547 0.072 Uiso 1 1 calc R U . . .
C37 C 0.12053(6) 0.00315(12) 0.80168(5) 0.0386(2) Uani 1 1 d . . . . .
C38 C 0.16289(7) 0.10797(13) 0.76633(6) 0.0425(3) Uani 1 1 d . . . . .
H38 H 0.168971 0.202348 0.784356 0.051 Uiso 1 1 calc R U . . .
C39 C 0.19634(8) 0.07278(15) 0.70404(6) 0.0516(3) Uani 1 1 d . . . . .
H39 H 0.226188 0.143163 0.680426 0.062 Uiso 1 1 calc R U . . .
C40 C 0.18619(9) -0.06423(16) 0.67656(7) 0.0567(3) Uani 1 1 d . . . . .
H40 H 0.208604 -0.087073 0.634185 0.068 Uiso 1 1 calc R U . . .
C41 C 0.14295(9) -0.16791(15) 0.71153(7) 0.0560(3) Uani 1 1 d . . . . .
H41 H 0.135433 -0.261229 0.692641 0.067 Uiso 1 1 calc R U . . .
C42 C 0.11068(8) -0.13521(14) 0.77414(6) 0.0478(3) Uani 1 1 d . . . . .
H42 H 0.082037 -0.206681 0.798097 0.057 Uiso 1 1 calc R U . . .
N1 N 0.31337(5) 0.24121(11) 0.99514(5) 0.0403(2) Uani 1 1 d . . . . .
N2 N 0.17740(6) 0.41813(11) 1.07361(5) 0.0453(2) Uani 1 1 d . . . . .
N3 N 0.08617(6) 0.03562(11) 0.86588(5) 0.0411(2) 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 N1 1.4039(13) . ?
C1 C6 1.4053(15) . ?
C1 C2 1.4054(15) . ?
C2 C3 1.4146(14) . ?
C2 C8 1.4537(14) . ?
C3 N3 1.3966(14) . ?
C3 C4 1.4044(15) . ?
C4 C5 1.4238(16) . ?
C4 C24 1.4558(15) . ?
C5 C6 1.4067(15) . ?
C5 C14 1.4508(15) . ?
C6 N2 1.4027(14) . ?
C7 C12 1.3941(15) . ?
C7 N1 1.3949(14) . ?
C7 C8 1.4075(15) . ?
C8 C9 1.3996(16) . ?
C9 C10 1.3828(17) . ?
C10 C11 1.3897(18) . ?
C11 C12 1.3781(18) . ?
C13 C18 1.3909(17) . ?
C13 N2 1.4017(15) . ?
C13 C14 1.4061(17) . ?
C14 C15 1.4000(16) . ?
C15 C16 1.3739(19) . ?
C16 C17 1.384(2) . ?
C17 C18 1.379(2) . ?
C19 C20 1.3929(17) . ?
C19 N3 1.4002(14) . ?
C19 C24 1.4024(17) . ?
C20 C21 1.3750(19) . ?
C21 C22 1.384(2) . ?
C22 C23 1.3747(19) . ?
C23 C24 1.3973(16) . ?
C25 C30 1.3748(18) . ?
C25 C26 1.3805(18) . ?
C25 N1 1.4313(14) . ?
C26 C27 1.383(2) . ?
C27 C28 1.354(3) . ?
C28 C29 1.376(3) . ?
C29 C30 1.390(2) . ?
C31 C32 1.3839(19) . ?
C31 C36 1.3856(19) . ?
C31 N2 1.4321(16) . ?
C32 C33 1.391(2) . ?
C33 C34 1.378(3) . ?
C34 C35 1.375(3) . ?
C35 C36 1.383(2) . ?
C37 C38 1.3837(16) . ?
C37 C42 1.3878(17) . ?
C37 N3 1.4227(14) . ?
C38 C39 1.3888(17) . ?
C39 C40 1.377(2) . ?
C40 C41 1.380(2) . ?
C41 C42 1.3811(18) . ?

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
N1 C1 C6 129.80(10) . . ?
N1 C1 C2 109.41(9) . . ?
C6 C1 C2 120.78(10) . . ?
C1 C2 C3 117.62(9) . . ?
C1 C2 C8 106.91(9) . . ?
C3 C2 C8 135.32(10) . . ?
N3 C3 C4 109.82(9) . . ?
N3 C3 C2 127.85(10) . . ?
C4 C3 C2 122.07(10) . . ?
C3 C4 C5 118.62(10) . . ?
C3 C4 C24 106.27(9) . . ?
C5 C4 C24 135.02(10) . . ?
C6 C5 C4 119.11(10) . . ?
C6 C5 C14 105.91(10) . . ?
C4 C5 C14 134.89(10) . . ?
N2 C6 C1 128.94(10) . . ?
N2 C6 C5 110.37(10) . . ?
C1 C6 C5 120.48(10) . . ?
C12 C7 N1 127.53(10) . . ?
C12 C7 C8 122.37(11) . . ?
N1 C7 C8 110.06(9) . . ?
C9 C8 C7 118.05(10) . . ?
C9 C8 C2 135.65(10) . . ?
C7 C8 C2 106.19(9) . . ?
C10 C9 C8 119.62(11) . . ?
C9 C10 C11 121.09(11) . . ?
C12 C11 C10 120.96(11) . . ?
C11 C12 C7 117.89(11) . . ?
C18 C13 N2 127.99(12) . . ?
C18 C13 C14 122.37(12) . . ?
N2 C13 C14 109.61(10) . . ?
C15 C14 C13 117.33(11) . . ?
C15 C14 C5 135.47(11) . . ?
C13 C14 C5 107.19(10) . . ?
C16 C15 C14 120.45(13) . . ?
C15 C16 C17 120.93(13) . . ?
C18 C17 C16 120.75(13) . . ?
C17 C18 C13 118.13(13) . . ?
C20 C19 N3 127.79(11) . . ?
C20 C19 C24 122.74(11) . . ?
N3 C19 C24 109.42(9) . . ?
C21 C20 C19 117.54(13) . . ?
C20 C21 C22 121.10(12) . . ?
C23 C22 C21 120.97(12) . . ?
C22 C23 C24 120.10(13) . . ?
C23 C24 C19 117.44(11) . . ?
C23 C24 C4 135.68(11) . . ?
C19 C24 C4 106.87(9) . . ?
C30 C25 C26 120.65(12) . . ?
C30 C25 N1 119.90(11) . . ?
C26 C25 N1 119.34(11) . . ?
C25 C26 C27 119.36(16) . . ?
C28 C27 C26 120.59(17) . . ?
C27 C28 C29 120.14(14) . . ?
C28 C29 C30 120.40(17) . . ?
C25 C30 C29 118.85(16) . . ?
C32 C31 C36 120.19(13) . . ?
C32 C31 N2 120.17(12) . . ?
C36 C31 N2 119.62(12) . . ?
C31 C32 C33 119.57(16) . . ?
C34 C33 C32 120.10(17) . . ?
C35 C34 C33 120.05(16) . . ?
C34 C35 C36 120.51(17) . . ?
C35 C36 C31 119.58(16) . . ?
C38 C37 C42 119.83(11) . . ?
C38 C37 N3 120.83(10) . . ?
C42 C37 N3 119.34(10) . . ?
C37 C38 C39 119.55(11) . . ?
C40 C39 C38 120.60(12) . . ?
C39 C40 C41 119.67(12) . . ?
C40 C41 C42 120.32(12) . . ?
C41 C42 C37 120.01(12) . . ?
C7 N1 C1 107.35(9) . . ?
C7 N1 C25 119.72(9) . . ?
C1 N1 C25 126.26(9) . . ?
C13 N2 C6 106.87(9) . . ?
C13 N2 C31 121.00(10) . . ?
C6 N2 C31 124.11(10) . . ?
C3 N3 C19 107.58(9) . . ?
C3 N3 C37 126.13(9) . . ?
C19 N3 C37 121.78(9) . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_abh-3-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2271797'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2023-06-23 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H39 N3'
_chemical_formula_weight         513.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.4937(2)
_cell_length_b                   24.0509(4)
_cell_length_c                   10.0306(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.017(2)
_cell_angle_gamma                90
_cell_volume                     2924.29(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    14542
_cell_measurement_theta_min      3.6540
_cell_measurement_theta_max      76.5360

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.517
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68357
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39094
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.646
_diffrn_reflns_theta_max         78.041
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6232
_reflns_number_gt                4888
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1075P)²+0.7453P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6232
_refine_ls_number_parameters     451
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.2211
_refine_ls_wR_factor_gt          0.2095
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C29' C 0.6838(2) 0.77824(10) 0.3680(3) 0.0879(7) Uani 0.542(8) 1 d D . P A 2
H29A H 0.639292 0.797771 0.289324 0.105 Uiso 0.542(8) 1 calc R U P A 2
H29B H 0.757977 0.775719 0.354570 0.105 Uiso 0.542(8) 1 calc R U P A 2
C25' C 0.9130(2) 0.70905(14) 0.3926(3) 0.0944(8) Uani 0.477(8) 1 d D . P B 2
H25A H 0.973766 0.734624 0.396748 0.113 Uiso 0.477(8) 1 calc R U P B 2
H25B H 0.849508 0.721220 0.322378 0.113 Uiso 0.477(8) 1 calc R U P B 2
C1 C 0.79152(16) 0.67456(8) 0.5418(2) 0.0607(5) Uani 1 1 d . . . . .
C2 C 0.81630(17) 0.63855(8) 0.6540(2) 0.0626(5) Uani 1 1 d . . . . .
C3 C 0.73248(17) 0.60268(8) 0.6777(2) 0.0621(5) Uani 1 1 d . . . . .
C4 C 0.62419(17) 0.60727(8) 0.5951(2) 0.0632(5) Uani 1 1 d . . . . .
C5 C 0.59549(16) 0.64801(8) 0.4891(2) 0.0605(5) Uani 1 1 d . . . . .
C6 C 0.68166(16) 0.68216(8) 0.46789(19) 0.0592(4) Uani 1 1 d . . . . .
C7 C 0.97021(17) 0.68749(10) 0.6401(2) 0.0713(6) Uani 1 1 d . . . . .
C8 C 1.0782(2) 0.70697(12) 0.6751(3) 0.0875(7) Uani 1 1 d . . . . .
H8 H 1.103929 0.731050 0.617323 0.105 Uiso 1 1 calc R U . . .
C9 C 1.1458(2) 0.68968(14) 0.7972(3) 0.1035(9) Uani 1 1 d . . . . .
H9 H 1.218383 0.702082 0.822343 0.124 Uiso 1 1 calc R U . . .
C10 C 1.1073(3) 0.65415(14) 0.8829(3) 0.1085(10) Uani 1 1 d . . . . .
H10 H 1.153992 0.643776 0.966198 0.130 Uiso 1 1 calc R U . . .
C11 C 1.0012(2) 0.63368(12) 0.8480(3) 0.0924(8) Uani 1 1 d . . . . .
H11 H 0.976651 0.609761 0.907174 0.111 Uiso 1 1 calc R U . . .
C12 C 0.93042(18) 0.64923(9) 0.7224(2) 0.0710(5) Uani 1 1 d . . . . .
C13 C 0.7331(2) 0.55703(9) 0.7714(2) 0.0705(5) Uani 1 1 d . . . . .
C14 C 0.8135(3) 0.52986(11) 0.8708(3) 0.0930(8) Uani 1 1 d . . . . .
H14 H 0.887003 0.540609 0.887105 0.112 Uiso 1 1 calc R U . . .
C15 C 0.7828(3) 0.48697(13) 0.9445(3) 0.1091(10) Uani 1 1 d . . . . .
H15 H 0.836039 0.469504 1.012590 0.131 Uiso 1 1 calc R U . . .
C16 C 0.6754(3) 0.46953(13) 0.9196(3) 0.1107(10) Uani 1 1 d . . . . .
H16 H 0.656962 0.440810 0.971941 0.133 Uiso 1 1 calc R U . . .
C17 C 0.5947(3) 0.49358(12) 0.8189(3) 0.1018(9) Uani 1 1 d . . . . .
H17 H 0.522202 0.481056 0.800607 0.122 Uiso 1 1 calc R U . . .
C18 C 0.6250(2) 0.53748(10) 0.7450(2) 0.0765(6) Uani 1 1 d . . . . .
C19 C 0.52863(17) 0.71220(9) 0.3202(2) 0.0656(5) Uani 1 1 d . . . . .
C20 C 0.4555(2) 0.74087(11) 0.2154(2) 0.0809(6) Uani 1 1 d . . . . .
H20 H 0.478937 0.770892 0.171434 0.097 Uiso 1 1 calc R U . . .
C21 C 0.3484(2) 0.72340(15) 0.1797(3) 0.0994(9) Uani 1 1 d . . . . .
H21 H 0.298324 0.741144 0.108735 0.119 Uiso 1 1 calc R U . . .
C22 C 0.3137(2) 0.67979(16) 0.2478(3) 0.1097(10) Uani 1 1 d . . . . .
H22 H 0.239965 0.669083 0.222920 0.132 Uiso 1 1 calc R U . . .
C23 C 0.3854(2) 0.65170(13) 0.3515(3) 0.0918(8) Uani 1 1 d . . . . .
H23 H 0.359960 0.622329 0.395762 0.110 Uiso 1 1 calc R U . . .
C24 C 0.49644(17) 0.66718(9) 0.3907(2) 0.0660(5) Uani 1 1 d . . . . .
C25 C 0.9130(2) 0.70905(14) 0.3926(3) 0.0944(8) Uani 0.523(8) 1 d D U P B 1
H25C H 0.842712 0.709616 0.325247 0.113 Uiso 0.523(8) 1 calc R U P B 1
H25D H 0.944098 0.745985 0.392125 0.113 Uiso 0.523(8) 1 calc R U P B 1
C26 C 0.9840(5) 0.6721(3) 0.3370(6) 0.0972(19) Uani 0.523(8) 1 d D U P B 1
H26A H 1.058143 0.672785 0.395739 0.117 Uiso 0.523(8) 1 calc R U P B 1
H26B H 0.987454 0.684788 0.246269 0.117 Uiso 0.523(8) 1 calc R U P B 1
C27 C 0.9390(6) 0.6136(3) 0.3281(8) 0.106(2) Uani 0.523(8) 1 d D U P B 1
H27A H 0.861213 0.614331 0.281824 0.127 Uiso 0.523(8) 1 calc R U P B 1
H27B H 0.945435 0.599469 0.420348 0.127 Uiso 0.523(8) 1 calc R U P B 1
C28 C 0.9984(16) 0.5745(4) 0.2519(17) 0.135(4) Uani 0.523(8) 1 d D U P B 1
H28A H 0.972841 0.580673 0.154852 0.202 Uiso 0.523(8) 1 calc R U P B 1
H28B H 0.983676 0.536758 0.272870 0.202 Uiso 0.523(8) 1 calc R U P B 1
H28C H 1.076322 0.581384 0.279798 0.202 Uiso 0.523(8) 1 calc R U P B 1
C26' C 0.9471(8) 0.6458(3) 0.3673(8) 0.114(3) Uani 0.477(8) 1 d D . P B 2
H26C H 1.003286 0.633604 0.446562 0.136 Uiso 0.477(8) 1 calc R U P B 2
H26D H 0.883145 0.622097 0.359820 0.136 Uiso 0.477(8) 1 calc R U P B 2
C27' C 0.9894(7) 0.6389(3) 0.2422(7) 0.123(3) Uani 0.477(8) 1 d D . P B 2
H27C H 1.051986 0.663594 0.249791 0.148 Uiso 0.477(8) 1 calc R U P B 2
H27D H 0.932442 0.651175 0.163762 0.148 Uiso 0.477(8) 1 calc R U P B 2
C28' C 1.0245(19) 0.5816(5) 0.2121(17) 0.150(6) Uani 0.477(8) 1 d D . P B 2
H28D H 1.057797 0.583066 0.135386 0.225 Uiso 0.477(8) 1 calc R U P B 2
H28E H 0.961198 0.557651 0.190417 0.225 Uiso 0.477(8) 1 calc R U P B 2
H28F H 1.076850 0.567504 0.291147 0.225 Uiso 0.477(8) 1 calc R U P B 2
C29 C 0.6838(2) 0.77824(10) 0.3680(3) 0.0879(7) Uani 0.458(8) 1 d D U P A 1
H29C H 0.676615 0.790673 0.274291 0.105 Uiso 0.458(8) 1 calc R U P A 1
H29D H 0.761539 0.778515 0.414547 0.105 Uiso 0.458(8) 1 calc R U P A 1
C30 C 0.6198(6) 0.8186(3) 0.4426(11) 0.118(3) Uani 0.458(8) 1 d D U P A 1
H30A H 0.563815 0.836685 0.371945 0.142 Uiso 0.458(8) 1 calc R U P A 1
H30B H 0.581072 0.795723 0.495486 0.142 Uiso 0.458(8) 1 calc R U P A 1
C31 C 0.6752(7) 0.8613(4) 0.5325(9) 0.128(3) Uani 0.458(8) 1 d D U P A 1
H31A H 0.696593 0.889711 0.475466 0.154 Uiso 0.458(8) 1 calc R U P A 1
H31B H 0.742817 0.845230 0.587497 0.154 Uiso 0.458(8) 1 calc R U P A 1
C32 C 0.6195(13) 0.8899(7) 0.6287(17) 0.111(4) Uani 0.458(8) 1 d D . P A 1
H32A H 0.542051 0.881625 0.603549 0.166 Uiso 0.458(8) 1 calc R U P A 1
H32B H 0.630032 0.929330 0.623906 0.166 Uiso 0.458(8) 1 calc R U P A 1
H32C H 0.650522 0.877245 0.720731 0.166 Uiso 0.458(8) 1 calc R U P A 1
C30' C 0.6883(7) 0.8123(2) 0.4899(7) 0.157(4) Uani 0.542(8) 1 d D . P A 2
H30D H 0.707200 0.788546 0.570349 0.188 Uiso 0.542(8) 1 calc R U P A 2
H30C H 0.747096 0.839340 0.497691 0.188 Uiso 0.542(8) 1 calc R U P A 2
C31' C 0.5883(8) 0.8414(4) 0.4912(10) 0.180(5) Uani 0.542(8) 1 d D . P A 2
H31C H 0.537126 0.815324 0.516043 0.217 Uiso 0.542(8) 1 calc R U P A 2
H31D H 0.555448 0.854417 0.398861 0.217 Uiso 0.542(8) 1 calc R U P A 2
C32' C 0.6022(15) 0.8911(7) 0.5895(18) 0.157(7) Uani 0.542(8) 1 d D . P A 2
H32D H 0.597891 0.925014 0.537988 0.236 Uiso 0.542(8) 1 calc R U P A 2
H32E H 0.672738 0.888906 0.654106 0.236 Uiso 0.542(8) 1 calc R U P A 2
H32F H 0.544810 0.890557 0.638102 0.236 Uiso 0.542(8) 1 calc R U P A 2
C33 C 0.4469(3) 0.54967(17) 0.5745(4) 0.0850(13) Uani 0.684(6) 1 d D U P C 1
H33A H 0.441538 0.509629 0.582324 0.102 Uiso 0.684(6) 1 calc R U P C 1
H33B H 0.429289 0.559117 0.477572 0.102 Uiso 0.684(6) 1 calc R U P C 1
C34 C 0.3653(4) 0.5775(3) 0.6426(6) 0.1216(18) Uani 0.684(6) 1 d D U P C 1
H34A H 0.374470 0.617456 0.638171 0.146 Uiso 0.684(6) 1 calc R U P C 1
H34B H 0.383213 0.567070 0.738912 0.146 Uiso 0.684(6) 1 calc R U P C 1
C35 C 0.2450(5) 0.5634(4) 0.5804(9) 0.151(3) Uani 0.684(6) 1 d D U P C 1
H35A H 0.201332 0.594831 0.597309 0.181 Uiso 0.684(6) 1 calc R U P C 1
H35B H 0.235450 0.560962 0.481741 0.181 Uiso 0.684(6) 1 calc R U P C 1
C36 C 0.1980(9) 0.5151(5) 0.6225(12) 0.235(6) Uani 0.684(6) 1 d D U P C 1
H36A H 0.178169 0.489733 0.546604 0.353 Uiso 0.684(6) 1 calc R U P C 1
H36B H 0.133365 0.525006 0.652845 0.353 Uiso 0.684(6) 1 calc R U P C 1
H36C H 0.250631 0.497736 0.696488 0.353 Uiso 0.684(6) 1 calc R U P C 1
C33' C 0.4381(7) 0.5835(4) 0.6524(9) 0.083(3) Uani 0.316(6) 1 d D . P C 2
H33C H 0.438653 0.588244 0.748563 0.099 Uiso 0.316(6) 1 calc R U P C 2
H33D H 0.415522 0.618373 0.605415 0.099 Uiso 0.316(6) 1 calc R U P C 2
C34' C 0.3581(6) 0.5385(4) 0.5908(11) 0.090(3) Uani 0.316(6) 1 d D . P C 2
H34C H 0.388371 0.502962 0.627649 0.108 Uiso 0.316(6) 1 calc R U P C 2
H34D H 0.351193 0.537684 0.492382 0.108 Uiso 0.316(6) 1 calc R U P C 2
C35' C 0.2437(9) 0.5446(7) 0.616(2) 0.222(16) Uani 0.316(6) 1 d D . P C 2
H35C H 0.249925 0.541616 0.714223 0.266 Uiso 0.316(6) 1 calc R U P C 2
H35D H 0.216672 0.581608 0.587973 0.266 Uiso 0.316(6) 1 calc R U P C 2
C36' C 0.1607(13) 0.5035(10) 0.545(2) 0.31(2) Uani 0.316(6) 1 d D . P C 2
H36D H 0.160588 0.502412 0.448933 0.458 Uiso 0.316(6) 1 calc R U P C 2
H36E H 0.088902 0.514229 0.554265 0.458 Uiso 0.316(6) 1 calc R U P C 2
H36F H 0.178849 0.467412 0.584428 0.458 Uiso 0.316(6) 1 calc R U P C 2
N1 N 0.88655(14) 0.70299(8) 0.52754(18) 0.0689(5) Uani 1 1 d . . . . .
N2 N 0.64057(14) 0.72202(7) 0.36751(17) 0.0642(4) Uani 1 1 d . . . . .
N3 N 0.55877(16) 0.56744(8) 0.6384(2) 0.0767(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C29' N2 1.456(3) . ?
C29' C30' 1.462(6) . ?
C29' H29A 0.9700 . ?
C29' H29B 0.9700 . ?
C25' N1 1.476(3) . ?
C25' C26' 1.615(7) . ?
C25' H25A 0.9700 . ?
C25' H25B 0.9700 . ?
C1 C2 1.394(3) . ?
C1 C6 1.405(3) . ?
C1 N1 1.407(3) . ?
C2 C3 1.421(3) . ?
C2 C12 1.448(3) . ?
C3 C4 1.409(3) . ?
C3 C13 1.444(3) . ?
C4 N3 1.395(3) . ?
C4 C5 1.426(3) . ?
C5 C6 1.411(3) . ?
C5 C24 1.458(3) . ?
C6 N2 1.395(2) . ?
C7 C8 1.390(3) . ?
C7 N1 1.391(3) . ?
C7 C12 1.405(3) . ?
C8 C9 1.373(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.403(3) . ?
C11 H11 0.9300 . ?
C13 C18 1.394(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.394(4) . ?
C17 H17 0.9300 . ?
C18 N3 1.385(3) . ?
C19 N2 1.384(3) . ?
C19 C20 1.396(3) . ?
C19 C24 1.405(3) . ?
C20 C21 1.365(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.398(3) . ?
C23 H23 0.9300 . ?
C25 C26 1.458(5) . ?
C25 N1 1.476(3) . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
C26 C27 1.512(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.514(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C26' C27' 1.485(7) . ?
C26' H26C 0.9700 . ?
C26' H26D 0.9700 . ?
C27' C28' 1.498(8) . ?
C27' H27C 0.9700 . ?
C27' H27D 0.9700 . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 0.9600 . ?
C29 N2 1.456(3) . ?
C29 C30 1.559(6) . ?
C29 H29C 0.9700 . ?
C29 H29D 0.9700 . ?
C30 C31 1.430(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.488(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C30' C31' 1.434(8) . ?
C30' H30D 0.9700 . ?
C30' H30C 0.9700 . ?
C31' C32' 1.533(9) . ?
C31' H31C 0.9700 . ?
C31' H31D 0.9700 . ?
C32' H32D 0.9600 . ?
C32' H32E 0.9600 . ?
C32' H32F 0.9600 . ?
C33 N3 1.453(4) . ?
C33 C34 1.514(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.520(7) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.411(8) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C33' C34' 1.502(8) . ?
C33' N3 1.595(9) . ?
C33' H33C 0.9700 . ?
C33' H33D 0.9700 . ?
C34' C35' 1.518(10) . ?
C34' H34C 0.9700 . ?
C34' H34D 0.9700 . ?
C35' C36' 1.485(10) . ?
C35' H35C 0.9700 . ?
C35' H35D 0.9700 . ?
C36' H36D 0.9600 . ?
C36' H36E 0.9600 . ?
C36' H36F 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
N2 C29' C30' 117.6(4) . . ?
N2 C29' H29A 107.9 . . ?
C30' C29' H29A 107.9 . . ?
N2 C29' H29B 107.9 . . ?
C30' C29' H29B 107.9 . . ?
H29A C29' H29B 107.2 . . ?
N1 C25' C26' 100.2(3) . . ?
N1 C25' H25A 111.7 . . ?
C26' C25' H25A 111.7 . . ?
N1 C25' H25B 111.7 . . ?
C26' C25' H25B 111.7 . . ?
H25A C25' H25B 109.5 . . ?
C2 C1 C6 120.30(18) . . ?
C2 C1 N1 110.87(17) . . ?
C6 C1 N1 128.56(18) . . ?
C1 C2 C3 118.93(18) . . ?
C1 C2 C12 105.85(18) . . ?
C3 C2 C12 135.22(19) . . ?
C4 C3 C2 119.72(18) . . ?
C4 C3 C13 107.19(19) . . ?
C2 C3 C13 133.04(19) . . ?
N3 C4 C3 108.34(18) . . ?
N3 C4 C5 130.04(19) . . ?
C3 C4 C5 121.62(18) . . ?
C6 C5 C4 116.70(18) . . ?
C6 C5 C24 105.49(17) . . ?
C4 C5 C24 137.79(19) . . ?
N2 C6 C1 127.74(18) . . ?
N2 C6 C5 110.38(17) . . ?
C1 C6 C5 121.88(18) . . ?
C8 C7 N1 127.4(2) . . ?
C8 C7 C12 122.2(2) . . ?
N1 C7 C12 110.45(19) . . ?
C9 C8 C7 118.2(3) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 117.8(2) . . ?
C11 C12 C2 135.4(2) . . ?
C7 C12 C2 106.60(18) . . ?
C18 C13 C14 118.3(2) . . ?
C18 C13 C3 106.28(19) . . ?
C14 C13 C3 135.4(2) . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 117.7(3) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
N3 C18 C13 110.0(2) . . ?
N3 C18 C17 128.0(2) . . ?
C13 C18 C17 122.0(2) . . ?
N2 C19 C20 126.7(2) . . ?
N2 C19 C24 110.34(17) . . ?
C20 C19 C24 123.0(2) . . ?
C21 C20 C19 117.8(3) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 116.7(2) . . ?
C23 C24 C5 136.7(2) . . ?
C19 C24 C5 106.57(18) . . ?
C26 C25 N1 125.7(3) . . ?
C26 C25 H25C 105.9 . . ?
N1 C25 H25C 105.9 . . ?
C26 C25 H25D 105.9 . . ?
N1 C25 H25D 105.9 . . ?
H25C C25 H25D 106.2 . . ?
C25 C26 C27 109.7(4) . . ?
C25 C26 H26A 109.7 . . ?
C27 C26 H26A 109.7 . . ?
C25 C26 H26B 109.7 . . ?
C27 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C26 C27 C28 112.7(6) . . ?
C26 C27 H27A 109.0 . . ?
C28 C27 H27A 109.0 . . ?
C26 C27 H27B 109.0 . . ?
C28 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27' C26' C25' 113.6(6) . . ?
C27' C26' H26C 108.9 . . ?
C25' C26' H26C 108.9 . . ?
C27' C26' H26D 108.9 . . ?
C25' C26' H26D 108.9 . . ?
H26C C26' H26D 107.7 . . ?
C26' C27' C28' 117.1(7) . . ?
C26' C27' H27C 108.0 . . ?
C28' C27' H27C 108.0 . . ?
C26' C27' H27D 108.0 . . ?
C28' C27' H27D 108.0 . . ?
H27C C27' H27D 107.3 . . ?
C27' C28' H28D 109.5 . . ?
C27' C28' H28E 109.5 . . ?
H28D C28' H28E 109.5 . . ?
C27' C28' H28F 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 109.5 . . ?
N2 C29 C30 110.3(4) . . ?
N2 C29 H29C 109.6 . . ?
C30 C29 H29C 109.6 . . ?
N2 C29 H29D 109.6 . . ?
C30 C29 H29D 109.6 . . ?
H29C C29 H29D 108.1 . . ?
C31 C30 C29 121.5(6) . . ?
C31 C30 H30A 106.9 . . ?
C29 C30 H30A 106.9 . . ?
C31 C30 H30B 106.9 . . ?
C29 C30 H30B 106.9 . . ?
H30A C30 H30B 106.7 . . ?
C30 C31 C32 120.7(8) . . ?
C30 C31 H31A 107.2 . . ?
C32 C31 H31A 107.2 . . ?
C30 C31 H31B 107.2 . . ?
C32 C31 H31B 107.2 . . ?
H31A C31 H31B 106.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31' C30' C29' 115.1(6) . . ?
C31' C30' H30D 108.5 . . ?
C29' C30' H30D 108.5 . . ?
C31' C30' H30C 108.5 . . ?
C29' C30' H30C 108.5 . . ?
H30D C30' H30C 107.5 . . ?
C30' C31' C32' 115.0(9) . . ?
C30' C31' H31C 108.5 . . ?
C32' C31' H31C 108.5 . . ?
C30' C31' H31D 108.5 . . ?
C32' C31' H31D 108.5 . . ?
H31C C31' H31D 107.5 . . ?
C31' C32' H32D 109.5 . . ?
C31' C32' H32E 109.5 . . ?
H32D C32' H32E 109.5 . . ?
C31' C32' H32F 109.5 . . ?
H32D C32' H32F 109.5 . . ?
H32E C32' H32F 109.5 . . ?
N3 C33 C34 110.6(4) . . ?
N3 C33 H33A 109.5 . . ?
C34 C33 H33A 109.5 . . ?
N3 C33 H33B 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C33 C34 C35 115.1(5) . . ?
C33 C34 H34A 108.5 . . ?
C35 C34 H34A 108.5 . . ?
C33 C34 H34B 108.5 . . ?
C35 C34 H34B 108.5 . . ?
H34A C34 H34B 107.5 . . ?
C36 C35 C34 120.1(7) . . ?
C36 C35 H35A 107.3 . . ?
C34 C35 H35A 107.3 . . ?
C36 C35 H35B 107.3 . . ?
C34 C35 H35B 107.3 . . ?
H35A C35 H35B 106.9 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34' C33' N3 109.8(6) . . ?
C34' C33' H33C 109.7 . . ?
N3 C33' H33C 109.7 . . ?
C34' C33' H33D 109.7 . . ?
N3 C33' H33D 109.7 . . ?
H33C C33' H33D 108.2 . . ?
C33' C34' C35' 114.9(8) . . ?
C33' C34' H34C 108.5 . . ?
C35' C34' H34C 108.5 . . ?
C33' C34' H34D 108.5 . . ?
C35' C34' H34D 108.5 . . ?
H34C C34' H34D 107.5 . . ?
C36' C35' C34' 115.5(11) . . ?
C36' C35' H35C 108.4 . . ?
C34' C35' H35C 108.4 . . ?
C36' C35' H35D 108.4 . . ?
C34' C35' H35D 108.4 . . ?
H35C C35' H35D 107.5 . . ?
C35' C36' H36D 109.5 . . ?
C35' C36' H36E 109.5 . . ?
H36D C36' H36E 109.5 . . ?
C35' C36' H36F 109.5 . . ?
H36D C36' H36F 109.5 . . ?
H36E C36' H36F 109.5 . . ?
C7 N1 C1 105.88(17) . . ?
C7 N1 C25 118.66(19) . . ?
C1 N1 C25 121.55(19) . . ?
C7 N1 C25' 118.66(19) . . ?
C1 N1 C25' 121.55(19) . . ?
C19 N2 C6 107.16(17) . . ?
C19 N2 C29 120.21(18) . . ?
C6 N2 C29 124.35(18) . . ?
C19 N2 C29' 120.21(18) . . ?
C6 N2 C29' 124.35(18) . . ?
C18 N3 C4 108.17(18) . . ?
C18 N3 C33 121.2(2) . . ?
C4 N3 C33 129.6(2) . . ?
C18 N3 C33' 117.3(4) . . ?
C4 N3 C33' 119.9(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
C6 C1 C2 C3 10.9(3) . . . . ?
N1 C1 C2 C3 -174.61(18) . . . . ?
C6 C1 C2 C12 -168.32(19) . . . . ?
N1 C1 C2 C12 6.2(2) . . . . ?
C1 C2 C3 C4 -5.3(3) . . . . ?
C12 C2 C3 C4 173.6(2) . . . . ?
C1 C2 C3 C13 171.5(2) . . . . ?
C12 C2 C3 C13 -9.6(4) . . . . ?
C2 C3 C4 N3 179.54(18) . . . . ?
C13 C3 C4 N3 2.0(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C13 C3 C4 C5 -178.81(19) . . . . ?
N3 C4 C5 C6 -178.8(2) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
N3 C4 C5 C24 2.8(4) . . . . ?
C3 C4 C5 C24 -176.2(2) . . . . ?
C2 C1 C6 N2 169.66(19) . . . . ?
N1 C1 C6 N2 -3.8(3) . . . . ?
C2 C1 C6 C5 -10.2(3) . . . . ?
N1 C1 C6 C5 176.37(19) . . . . ?
C4 C5 C6 N2 -176.39(17) . . . . ?
C24 C5 C6 N2 2.5(2) . . . . ?
C4 C5 C6 C1 3.5(3) . . . . ?
C24 C5 C6 C1 -177.68(18) . . . . ?
N1 C7 C8 C9 174.7(3) . . . . ?
C12 C7 C8 C9 -2.8(4) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C9 C10 C11 1.7(6) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C7 -2.9(4) . . . . ?
C10 C11 C12 C2 -177.3(3) . . . . ?
C8 C7 C12 C11 4.4(4) . . . . ?
N1 C7 C12 C11 -173.5(2) . . . . ?
C8 C7 C12 C2 -179.7(2) . . . . ?
N1 C7 C12 C2 2.4(3) . . . . ?
C1 C2 C12 C11 169.6(3) . . . . ?
C3 C2 C12 C11 -9.3(5) . . . . ?
C1 C2 C12 C7 -5.2(2) . . . . ?
C3 C2 C12 C7 175.8(2) . . . . ?
C4 C3 C13 C18 -2.2(2) . . . . ?
C2 C3 C13 C18 -179.2(2) . . . . ?
C4 C3 C13 C14 175.5(3) . . . . ?
C2 C3 C13 C14 -1.6(5) . . . . ?
C18 C13 C14 C15 -3.6(4) . . . . ?
C3 C13 C14 C15 179.0(3) . . . . ?
C13 C14 C15 C16 1.8(5) . . . . ?
C14 C15 C16 C17 0.9(6) . . . . ?
C15 C16 C17 C18 -1.6(6) . . . . ?
C14 C13 C18 N3 -176.6(2) . . . . ?
C3 C13 C18 N3 1.6(3) . . . . ?
C14 C13 C18 C17 2.9(4) . . . . ?
C3 C13 C18 C17 -178.9(3) . . . . ?
C16 C17 C18 N3 179.1(3) . . . . ?
C16 C17 C18 C13 -0.3(5) . . . . ?
N2 C19 C20 C21 177.4(2) . . . . ?
C24 C19 C20 C21 -1.0(4) . . . . ?
C19 C20 C21 C22 1.6(4) . . . . ?
C20 C21 C22 C23 -1.3(5) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C19 0.5(4) . . . . ?
C22 C23 C24 C5 -178.1(3) . . . . ?
N2 C19 C24 C23 -178.7(2) . . . . ?
C20 C19 C24 C23 -0.1(3) . . . . ?
N2 C19 C24 C5 0.3(2) . . . . ?
C20 C19 C24 C5 178.9(2) . . . . ?
C6 C5 C24 C23 177.1(3) . . . . ?
C4 C5 C24 C23 -4.4(5) . . . . ?
C6 C5 C24 C19 -1.7(2) . . . . ?
C4 C5 C24 C19 176.8(2) . . . . ?
N1 C25 C26 C27 58.7(6) . . . . ?
C25 C26 C27 C28 171.5(10) . . . . ?
N1 C25' C26' C27' -174.5(7) . . . . ?
C25' C26' C27' C28' 179.1(12) . . . . ?
N2 C29 C30 C31 139.8(9) . . . . ?
C29 C30 C31 C32 -164.7(12) . . . . ?
N2 C29' C30' C31' -85.2(8) . . . . ?
C29' C30' C31' C32' -160.1(11) . . . . ?
N3 C33 C34 C35 178.0(5) . . . . ?
C33 C34 C35 C36 85.0(11) . . . . ?
N3 C33' C34' C35' 171.4(9) . . . . ?
C33' C34' C35' C36' 174.3(16) . . . . ?
C8 C7 N1 C1 -176.4(2) . . . . ?
C12 C7 N1 C1 1.3(3) . . . . ?
C8 C7 N1 C25 42.7(4) . . . . ?
C12 C7 N1 C25 -139.5(2) . . . . ?
C8 C7 N1 C25' 42.7(4) . . . . ?
C12 C7 N1 C25' -139.5(2) . . . . ?
C2 C1 N1 C7 -4.8(2) . . . . ?
C6 C1 N1 C7 169.2(2) . . . . ?
C2 C1 N1 C25 134.7(2) . . . . ?
C6 C1 N1 C25 -51.4(3) . . . . ?
C2 C1 N1 C25' 134.7(2) . . . . ?
C6 C1 N1 C25' -51.4(3) . . . . ?
C26 C25 N1 C7 40.9(5) . . . . ?
C26 C25 N1 C1 -93.7(4) . . . . ?
C26' C25' N1 C7 63.6(4) . . . . ?
C26' C25' N1 C1 -71.0(4) . . . . ?
C20 C19 N2 C6 -177.3(2) . . . . ?
C24 C19 N2 C6 1.2(2) . . . . ?
C20 C19 N2 C29 33.0(3) . . . . ?
C24 C19 N2 C29 -148.5(2) . . . . ?
C20 C19 N2 C29' 33.0(3) . . . . ?
C24 C19 N2 C29' -148.5(2) . . . . ?
C1 C6 N2 C19 177.84(19) . . . . ?
C5 C6 N2 C19 -2.3(2) . . . . ?
C1 C6 N2 C29 -34.1(3) . . . . ?
C5 C6 N2 C29 145.8(2) . . . . ?
C1 C6 N2 C29' -34.1(3) . . . . ?
C5 C6 N2 C29' 145.8(2) . . . . ?
C30 C29 N2 C19 52.2(5) . . . . ?
C30 C29 N2 C6 -92.0(5) . . . . ?
C30' C29' N2 C19 88.5(4) . . . . ?
C30' C29' N2 C6 -55.7(4) . . . . ?
C13 C18 N3 C4 -0.3(3) . . . . ?
C17 C18 N3 C4 -179.8(3) . . . . ?
C13 C18 N3 C33 169.4(3) . . . . ?
C17 C18 N3 C33 -10.1(4) . . . . ?
C13 C18 N3 C33' -139.8(4) . . . . ?
C17 C18 N3 C33' 40.7(5) . . . . ?
C3 C4 N3 C18 -1.1(2) . . . . ?
C5 C4 N3 C18 179.8(2) . . . . ?
C3 C4 N3 C33 -169.6(3) . . . . ?
C5 C4 N3 C33 11.3(4) . . . . ?
C3 C4 N3 C33' 137.2(4) . . . . ?
C5 C4 N3 C33' -41.9(5) . . . . ?
C34 C33 N3 C18 92.9(4) . . . . ?
C34 C33 N3 C4 -99.8(4) . . . . ?
C34' C33' N3 C18 -90.0(7) . . . . ?
C34' C33' N3 C4 135.4(6) . . . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_abh-diwu_auto_sq_sq
_database_code_depnum_ccdc_archive 'CCDC 2309597'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N O4'
_chemical_formula_weight         334.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.01120(10)
_cell_length_b                   15.7452(2)
_cell_length_c                   19.7395(2)
_cell_angle_alpha                83.7750(10)
_cell_angle_beta                 82.4220(10)
_cell_angle_gamma                80.2710(10)
_cell_volume                     1818.23(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    21259
_cell_measurement_theta_min      2.2570
_cell_measurement_theta_max      77.6080

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86462
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33950
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         85.192
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7667
_reflns_number_gt                6581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0952P)²+0.3961P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7667
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1530
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
O20 O 1.21235(17) 0.68858(9) 0.37799(7) 0.0635(3) Uani 1 1 d . . . . .
H20 H 1.232548 0.731407 0.351789 0.095 Uiso 1 1 calc R U . . .
O45 O 0.94501(19) 0.26765(9) 0.27771(7) 0.0669(3) Uani 1 1 d . . . . .
H45 H 0.993527 0.249998 0.240141 0.100 Uiso 1 1 calc R U . . .
O46 O 0.0984(2) 0.43027(8) 0.33870(7) 0.0652(3) Uani 1 1 d . . . . .
O21 O 0.5486(2) 0.51410(8) 0.35875(8) 0.0681(3) Uani 1 1 d . . . . .
N1 N 0.7204(2) 0.63131(8) 0.32018(7) 0.0482(3) Uani 1 1 d . . . . .
N26 N 0.3699(2) 0.37225(8) 0.25781(6) 0.0471(3) Uani 1 1 d . . . . .
O25 O 1.1541(2) 0.82816(10) 0.29054(8) 0.0778(4) Uani 1 1 d . . . . .
O23 O 0.9985(3) 0.85491(11) 0.19282(8) 0.0887(5) Uani 1 1 d . . . . .
O48 O 0.8201(3) 0.32046(12) 0.05964(7) 0.0934(5) Uani 1 1 d . . . . .
O50 O 0.9797(3) 0.24274(13) 0.14660(9) 0.0953(5) Uani 1 1 d . . . . .
C2 C 0.8698(2) 0.68810(9) 0.32627(8) 0.0470(3) Uani 1 1 d . . . . .
C27 C 0.5793(2) 0.32301(9) 0.23782(8) 0.0478(3) Uani 1 1 d . . . . .
C34 C 0.2798(3) 0.41630(10) 0.19927(8) 0.0513(3) Uani 1 1 d . . . . .
C14 C 0.8578(2) 0.76094(9) 0.43384(7) 0.0468(3) Uani 1 1 d . . . . .
C3 C 0.8884(3) 0.74127(10) 0.26665(8) 0.0525(3) Uani 1 1 d . . . . .
C35 C 0.7083(2) 0.26489(10) 0.29100(8) 0.0504(3) Uani 1 1 d . . . . .
C13 C 0.6557(2) 0.56709(9) 0.37143(9) 0.0530(3) Uani 1 1 d . . . . .
C10 C 0.9759(2) 0.68560(10) 0.39226(8) 0.0491(3) Uani 1 1 d . . . . .
C4 C 0.7425(3) 0.71762(11) 0.22088(8) 0.0546(4) Uani 1 1 d . . . . .
C38 C 0.2672(3) 0.37900(10) 0.32595(8) 0.0507(3) Uani 1 1 d . . . . .
C28 C 0.6262(3) 0.33618(11) 0.16794(8) 0.0549(4) Uani 1 1 d . . . . .
C9 C 0.6412(3) 0.64915(11) 0.25559(8) 0.0519(3) Uani 1 1 d . . . . .
C39 C 0.6617(3) 0.17167(10) 0.29346(8) 0.0531(3) Uani 1 1 d . . . . .
C19 C 0.6340(3) 0.79812(11) 0.43063(10) 0.0576(4) Uani 1 1 d . . . . .
H19 H 0.549733 0.779296 0.400552 0.069 Uiso 1 1 calc R U . . .
C29 C 0.4369(3) 0.39587(11) 0.14251(8) 0.0559(4) Uani 1 1 d . . . . .
C11 C 0.9604(3) 0.59898(11) 0.43476(9) 0.0589(4) Uani 1 1 d . . . . .
H11A H 1.071269 0.554234 0.413943 0.071 Uiso 1 1 calc R U . . .
H11B H 0.997855 0.602833 0.480534 0.071 Uiso 1 1 calc R U . . .
C22 C 1.0278(3) 0.81051(12) 0.25295(10) 0.0623(4) Uani 1 1 d . . . . .
C36 C 0.6378(3) 0.30011(11) 0.36112(9) 0.0599(4) Uani 1 1 d . . . . .
H36A H 0.702468 0.258673 0.396097 0.072 Uiso 1 1 calc R U . . .
H36B H 0.698258 0.353370 0.361525 0.072 Uiso 1 1 calc R U . . .
C12 C 0.7264(3) 0.57376(11) 0.43989(9) 0.0614(4) Uani 1 1 d . . . . .
H12A H 0.725755 0.518522 0.466911 0.074 Uiso 1 1 calc R U . . .
H12B H 0.617112 0.616481 0.463589 0.074 Uiso 1 1 calc R U . . .
C37 C 0.3823(3) 0.31741(12) 0.37804(9) 0.0632(4) Uani 1 1 d . . . . .
H37A H 0.323815 0.263133 0.381508 0.076 Uiso 1 1 calc R U . . .
H37B H 0.345660 0.340707 0.422387 0.076 Uiso 1 1 calc R U . . .
C33 C 0.0711(3) 0.46934(12) 0.19351(11) 0.0649(4) Uani 1 1 d . . . . .
H33 H -0.033201 0.481221 0.231785 0.078 Uiso 1 1 calc R U . . .
C18 C 0.5334(3) 0.86344(12) 0.47198(11) 0.0680(5) Uani 1 1 d . . . . .
H18 H 0.382314 0.887829 0.469522 0.082 Uiso 1 1 calc R U . . .
C15 C 0.9792(3) 0.79129(13) 0.47873(9) 0.0638(4) Uani 1 1 d . . . . .
H15 H 1.130157 0.767087 0.481724 0.077 Uiso 1 1 calc R U . . .
C47 C 0.8254(3) 0.29495(14) 0.12617(10) 0.0701(5) Uani 1 1 d . . . . .
C17 C 0.6553(4) 0.89208(12) 0.51626(10) 0.0710(5) Uani 1 1 d . . . . .
H17 H 0.586858 0.935185 0.544371 0.085 Uiso 1 1 calc R U . . .
C44 C 0.8108(4) 0.10511(12) 0.32296(10) 0.0683(5) Uani 1 1 d . . . . .
H44 H 0.939656 0.117516 0.338857 0.082 Uiso 1 1 calc R U . . .
C5 C 0.6867(4) 0.74954(15) 0.15538(10) 0.0707(5) Uani 1 1 d . . . . .
H5 H 0.752787 0.794713 0.131089 0.085 Uiso 1 1 calc R U . . .
C8 C 0.4822(3) 0.61225(13) 0.22794(10) 0.0654(4) Uani 1 1 d . . . . .
H8 H 0.414459 0.567276 0.251897 0.079 Uiso 1 1 calc R U . . .
C30 C 0.3879(4) 0.43256(14) 0.07721(10) 0.0729(5) Uani 1 1 d . . . . .
H30 H 0.491075 0.421154 0.038613 0.087 Uiso 1 1 calc R U . . .
C16 C 0.8790(4) 0.85679(14) 0.51890(10) 0.0743(5) Uani 1 1 d . . . . .
H16 H 0.963599 0.877206 0.548011 0.089 Uiso 1 1 calc R U . . .
C6 C 0.5313(4) 0.71248(17) 0.12762(11) 0.0808(6) Uani 1 1 d . . . . .
H6 H 0.493426 0.732786 0.083942 0.097 Uiso 1 1 calc R U . . .
C32 C 0.0266(4) 0.50326(15) 0.12850(13) 0.0785(6) Uani 1 1 d . . . . .
H32 H -0.111302 0.538533 0.122631 0.094 Uiso 1 1 calc R U . . .
C7 C 0.4303(4) 0.64546(17) 0.16359(11) 0.0790(6) Uani 1 1 d . . . . .
H7 H 0.324764 0.622409 0.143618 0.095 Uiso 1 1 calc R U . . .
C31 C 0.1835(4) 0.48588(16) 0.07153(12) 0.0818(6) Uani 1 1 d . . . . .
H31 H 0.149625 0.510896 0.028477 0.098 Uiso 1 1 calc R U . . .
C40 C 0.4749(3) 0.15062(13) 0.26988(13) 0.0775(6) Uani 1 1 d . . . . .
H40 H 0.373305 0.193751 0.249278 0.093 Uiso 1 1 calc R U . . .
C43 C 0.7701(5) 0.02056(14) 0.32900(12) 0.0877(7) Uani 1 1 d . . . . .
H43 H 0.870679 -0.023246 0.349297 0.105 Uiso 1 1 calc R U . . .
C42 C 0.5827(5) 0.00110(14) 0.30527(14) 0.0938(8) Uani 1 1 d . . . . .
H42 H 0.556351 -0.055837 0.308885 0.113 Uiso 1 1 calc R U . . .
C41 C 0.4363(4) 0.06513(16) 0.27658(17) 0.0980(8) Uani 1 1 d . . . . .
H41 H 0.307695 0.052032 0.261031 0.118 Uiso 1 1 calc R U . . .
C24 C 1.1316(6) 0.9243(2) 0.17458(16) 0.1194(11) Uani 1 1 d . . . . .
H24A H 1.122712 0.944964 0.127286 0.179 Uiso 1 1 calc R U . . .
H24B H 1.287164 0.903244 0.181422 0.179 Uiso 1 1 calc R U . . .
H24C H 1.073096 0.970748 0.202950 0.179 Uiso 1 1 calc R U . . .
C49 C 1.0126(6) 0.2852(2) 0.01359(15) 0.1234(12) Uani 1 1 d . . . . .
H49A H 0.995331 0.310074 -0.032363 0.185 Uiso 1 1 calc R U . . .
H49B H 1.020804 0.223541 0.015396 0.185 Uiso 1 1 calc R U . . .
H49C H 1.149628 0.298386 0.027162 0.185 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
O20 C10 1.4200(17) . ?
O45 C35 1.4197(18) . ?
O46 C38 1.2019(19) . ?
O21 C13 1.2011(19) . ?
N1 C2 1.3942(18) . ?
N1 C9 1.403(2) . ?
N1 C13 1.416(2) . ?
N26 C27 1.3952(19) . ?
N26 C34 1.405(2) . ?
N26 C38 1.4113(19) . ?
O25 C22 1.212(2) . ?
O23 C22 1.327(2) . ?
O23 C24 1.448(3) . ?
O48 C47 1.334(3) . ?
O48 C49 1.445(3) . ?
O50 C47 1.211(3) . ?
C2 C3 1.372(2) . ?
C2 C10 1.518(2) . ?
C27 C28 1.371(2) . ?
C27 C35 1.519(2) . ?
C34 C29 1.395(2) . ?
C34 C33 1.396(2) . ?
C14 C19 1.381(2) . ?
C14 C15 1.388(2) . ?
C14 C10 1.535(2) . ?
C3 C4 1.455(2) . ?
C3 C22 1.466(2) . ?
C35 C36 1.528(2) . ?
C35 C39 1.535(2) . ?
C13 C12 1.488(3) . ?
C10 C11 1.532(2) . ?
C4 C5 1.398(3) . ?
C4 C9 1.398(2) . ?
C38 C37 1.490(2) . ?
C28 C29 1.455(2) . ?
C28 C47 1.459(2) . ?
C9 C8 1.394(2) . ?
C39 C40 1.373(3) . ?
C39 C44 1.389(2) . ?
C19 C18 1.390(2) . ?
C29 C30 1.401(2) . ?
C11 C12 1.513(3) . ?
C36 C37 1.513(3) . ?
C33 C32 1.377(3) . ?
C18 C17 1.367(3) . ?
C15 C16 1.377(3) . ?
C17 C16 1.371(3) . ?
C44 C43 1.384(3) . ?
C5 C6 1.379(3) . ?
C8 C7 1.375(3) . ?
C30 C31 1.376(3) . ?
C6 C7 1.388(4) . ?
C32 C31 1.389(4) . ?
C40 C41 1.394(3) . ?
C43 C42 1.367(4) . ?
C42 C41 1.349(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 109.03(13) . . ?
C2 N1 C13 125.47(13) . . ?
C9 N1 C13 125.49(13) . . ?
C27 N26 C34 109.10(12) . . ?
C27 N26 C38 125.71(13) . . ?
C34 N26 C38 125.17(13) . . ?
C22 O23 C24 115.5(2) . . ?
C47 O48 C49 116.4(2) . . ?
C3 C2 N1 108.61(13) . . ?
C3 C2 C10 130.85(13) . . ?
N1 C2 C10 120.52(13) . . ?
C28 C27 N26 108.56(13) . . ?
C28 C27 C35 131.40(14) . . ?
N26 C27 C35 120.00(13) . . ?
C29 C34 C33 122.66(16) . . ?
C29 C34 N26 107.58(13) . . ?
C33 C34 N26 129.73(16) . . ?
C19 C14 C15 118.18(14) . . ?
C19 C14 C10 123.23(13) . . ?
C15 C14 C10 118.55(14) . . ?
C2 C3 C4 107.84(14) . . ?
C2 C3 C22 125.42(15) . . ?
C4 C3 C22 126.73(16) . . ?
O45 C35 C27 111.05(13) . . ?
O45 C35 C36 104.61(13) . . ?
C27 C35 C36 109.21(13) . . ?
O45 C35 C39 110.67(12) . . ?
C27 C35 C39 110.67(13) . . ?
C36 C35 C39 110.48(13) . . ?
O21 C13 N1 120.71(16) . . ?
O21 C13 C12 124.99(16) . . ?
N1 C13 C12 114.29(13) . . ?
O20 C10 C2 110.69(12) . . ?
O20 C10 C11 104.75(13) . . ?
C2 C10 C11 110.11(12) . . ?
O20 C10 C14 110.31(12) . . ?
C2 C10 C14 110.44(12) . . ?
C11 C10 C14 110.42(13) . . ?
C5 C4 C9 119.16(16) . . ?
C5 C4 C3 134.08(17) . . ?
C9 C4 C3 106.74(14) . . ?
O46 C38 N26 120.80(15) . . ?
O46 C38 C37 124.58(15) . . ?
N26 C38 C37 114.61(13) . . ?
C27 C28 C29 107.74(14) . . ?
C27 C28 C47 126.20(16) . . ?
C29 C28 C47 126.02(16) . . ?
C8 C9 C4 122.49(16) . . ?
C8 C9 N1 129.65(16) . . ?
C4 C9 N1 107.79(13) . . ?
C40 C39 C44 117.86(17) . . ?
C40 C39 C35 123.23(15) . . ?
C44 C39 C35 118.87(16) . . ?
C14 C19 C18 120.54(16) . . ?
C34 C29 C30 118.94(17) . . ?
C34 C29 C28 107.01(14) . . ?
C30 C29 C28 134.05(17) . . ?
C12 C11 C10 112.30(13) . . ?
O25 C22 O23 122.07(17) . . ?
O25 C22 C3 126.33(18) . . ?
O23 C22 C3 111.59(16) . . ?
C37 C36 C35 111.92(14) . . ?
C13 C12 C11 112.41(15) . . ?
C38 C37 C36 113.04(14) . . ?
C32 C33 C34 116.91(19) . . ?
C17 C18 C19 120.44(17) . . ?
C16 C15 C14 120.88(17) . . ?
O50 C47 O48 121.72(18) . . ?
O50 C47 C28 126.51(18) . . ?
O48 C47 C28 111.75(18) . . ?
C18 C17 C16 119.51(16) . . ?
C43 C44 C39 120.8(2) . . ?
C6 C5 C4 118.4(2) . . ?
C7 C8 C9 116.84(19) . . ?
C31 C30 C29 118.4(2) . . ?
C17 C16 C15 120.43(18) . . ?
C5 C6 C7 121.29(19) . . ?
C33 C32 C31 121.35(19) . . ?
C8 C7 C6 121.77(18) . . ?
C30 C31 C32 121.64(19) . . ?
C39 C40 C41 120.5(2) . . ?
C42 C43 C44 120.3(2) . . ?
C41 C42 C43 119.5(2) . . ?
C42 C41 C40 121.0(2) . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_abh-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2271810'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2023-06-23 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N O4'
_chemical_formula_weight         365.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   27.5274(3)
_cell_length_b                   9.94060(10)
_cell_length_c                   27.6836(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7575.31(14)
_cell_formula_units_Z            16
_cell_measurement_temperature    278(2)
_cell_measurement_reflns_used    41061
_cell_measurement_theta_min      3.1500
_cell_measurement_theta_max      77.9260

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             3104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.714
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8143
_exptl_absorpt_correction_T_max  0.9129
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      278(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            89928
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.193
_diffrn_reflns_theta_max         66.987
_diffrn_reflns_theta_full        66.987
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             13366
_reflns_number_gt                12497
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.982

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.6035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 5690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         13366
_refine_ls_number_parameters     990
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

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
O22 O 0.39742(6) 0.23779(19) 0.54191(7) 0.0505(4) Uani 1 1 d . . . . .
H22 H 0.375618 0.261031 0.560288 0.076 Uiso 1 1 calc R U . . .
O53 O 0.32523(6) 0.2955(2) 0.60586(8) 0.0602(5) Uani 1 1 d . . . . .
O54 O 0.13297(6) 0.44542(19) 0.59500(8) 0.0536(4) Uani 1 1 d . . . . .
H54 H 0.124234 0.367103 0.591680 0.080 Uiso 1 1 calc R U . . .
O25 O 0.40787(7) 0.5935(2) 0.52312(8) 0.0646(5) Uani 1 1 d . . . . .
O80 O 0.96757(6) 0.2734(2) 0.40779(8) 0.0595(5) Uani 1 1 d . . . . .
N82 N 0.62565(7) 0.38424(18) 0.35834(8) 0.0404(4) Uani 1 1 d . . . . .
N28 N 0.25338(6) 0.34080(19) 0.64087(7) 0.0381(4) Uani 1 1 d . . . . .
O103 O 0.50508(6) 0.48804(18) 0.40405(8) 0.0532(4) Uani 1 1 d . . . . .
H103 H 0.496149 0.409723 0.406846 0.080 Uiso 1 1 calc R U . . .
O50 O 0.11706(7) 0.5010(2) 0.72516(9) 0.0696(6) Uani 1 1 d . . . . .
O81 O 0.77180(6) 0.2297(2) 0.43886(7) 0.0583(5) Uani 1 1 d . . . . .
H81 H 0.752005 0.274891 0.423797 0.087 Uiso 1 1 calc R U . . .
O77 O 0.75707(8) 0.6487(2) 0.42053(8) 0.0631(5) Uani 1 1 d . . . . .
O23 O 0.59090(6) 0.3103(2) 0.58024(10) 0.0693(6) Uani 1 1 d . . . . .
O104 O 0.69861(7) 0.3561(3) 0.39288(9) 0.0747(6) Uani 1 1 d . . . . .
N1 N 0.51408(7) 0.3897(2) 0.57888(8) 0.0442(5) Uani 1 1 d . . . . .
O106 O 0.48990(8) 0.5277(2) 0.26909(9) 0.0726(6) Uani 1 1 d . . . . .
C95 C 0.57099(7) 0.6419(2) 0.40630(9) 0.0381(5) Uani 1 1 d . . . . .
C29 C 0.26738(8) 0.3284(2) 0.68998(9) 0.0426(5) Uani 1 1 d . . . . .
O79 O 0.79464(12) 0.5580(3) 0.48306(9) 0.0995(10) Uani 1 1 d . . . . .
C36 C 0.28253(8) 0.3292(2) 0.60163(9) 0.0430(5) Uani 1 1 d . . . . .
C68 C 0.81071(8) 0.1892(2) 0.35994(10) 0.0436(5) Uani 1 1 d . . . . .
C90 C 0.57294(7) 0.4138(2) 0.36002(9) 0.0381(5) Uani 1 1 d . . . . .
H90 H 0.556412 0.326602 0.361747 0.046 Uiso 1 1 calc R U . . .
O27 O 0.36149(8) 0.6089(3) 0.58780(10) 0.0798(7) Uani 1 1 d . . . . .
N55 N 0.89296(7) 0.3694(2) 0.41017(8) 0.0443(4) Uani 1 1 d . . . . .
C14 C 0.43637(8) 0.1719(2) 0.61803(9) 0.0424(5) Uani 1 1 d . . . . .
C32 C 0.20086(7) 0.3731(2) 0.63894(9) 0.0378(5) Uani 1 1 d . . . . .
H32 H 0.183654 0.286811 0.637957 0.045 Uiso 1 1 calc R U . . .
C96 C 0.54749(8) 0.7335(2) 0.43752(9) 0.0439(5) Uani 1 1 d . . . . .
O108 O 0.49739(9) 0.3144(3) 0.29344(11) 0.0845(8) Uani 1 1 d . . . . .
C46 C 0.23993(8) 0.6463(2) 0.61682(10) 0.0434(5) Uani 1 1 d . . . . .
H46 H 0.258489 0.584880 0.634199 0.052 Uiso 1 1 calc R U . . .
O52 O 0.12378(9) 0.2851(2) 0.70562(12) 0.0916(9) Uani 1 1 d . . . . .
C83 C 0.63990(8) 0.3707(2) 0.30917(10) 0.0436(5) Uani 1 1 d . . . . .
C94 C 0.55670(8) 0.4933(2) 0.40469(9) 0.0404(5) Uani 1 1 d . . . . .
C35 C 0.26110(9) 0.3656(3) 0.55350(10) 0.0493(6) Uani 1 1 d . . . . .
H35A H 0.271664 0.299007 0.530141 0.059 Uiso 1 1 calc R U . . .
H35B H 0.274664 0.451364 0.543652 0.059 Uiso 1 1 calc R U . . .
C45 C 0.25436(9) 0.7791(3) 0.61592(11) 0.0492(6) Uani 1 1 d . . . . .
H45 H 0.282876 0.804479 0.631465 0.059 Uiso 1 1 calc R U . . .
C33 C 0.18460(7) 0.4518(2) 0.59406(9) 0.0393(5) Uani 1 1 d . . . . .
C41 C 0.19870(7) 0.6004(2) 0.59276(9) 0.0385(5) Uani 1 1 d . . . . .
C88 C 0.60315(9) 0.4199(2) 0.27979(10) 0.0448(5) Uani 1 1 d . . . . .
C73 C 0.83513(9) 0.2572(3) 0.32362(9) 0.0474(5) Uani 1 1 d . . . . .
H73 H 0.852547 0.334280 0.331583 0.057 Uiso 1 1 calc R U . . .
C24 C 0.39709(8) 0.5674(2) 0.56862(10) 0.0474(6) Uani 1 1 d . . . . .
C100 C 0.60818(8) 0.6917(2) 0.37702(9) 0.0406(5) Uani 1 1 d . . . . .
H100 H 0.625157 0.632137 0.357383 0.049 Uiso 1 1 calc R U . . .
C30 C 0.23093(9) 0.3804(2) 0.71920(9) 0.0452(5) Uani 1 1 d . . . . .
C15 C 0.45852(9) 0.2289(3) 0.65857(10) 0.0470(5) Uani 1 1 d . . . . .
H15 H 0.476825 0.306771 0.654601 0.056 Uiso 1 1 calc R U . . .
C76 C 0.78886(10) 0.5668(3) 0.44063(11) 0.0547(6) Uani 1 1 d . . . . .
C91 C 0.65518(9) 0.3796(2) 0.39724(10) 0.0481(6) Uani 1 1 d . . . . .
C89 C 0.56123(8) 0.4722(2) 0.30995(9) 0.0422(5) Uani 1 1 d . . . . .
H89 H 0.562340 0.570703 0.311220 0.051 Uiso 1 1 calc R U . . .
C19 C 0.40934(9) 0.0528(3) 0.62562(11) 0.0521(6) Uani 1 1 d . . . . .
C31 C 0.18987(8) 0.4354(2) 0.68847(9) 0.0424(5) Uani 1 1 d . . . . .
H31 H 0.192302 0.533643 0.686517 0.051 Uiso 1 1 calc R U . . .
C9 C 0.46183(7) 0.3772(2) 0.56494(9) 0.0403(5) Uani 1 1 d . . . . .
H9 H 0.459627 0.404499 0.530998 0.048 Uiso 1 1 calc R U . . .
C99 C 0.62060(9) 0.8256(3) 0.37614(10) 0.0483(6) Uani 1 1 d . . . . .
H99 H 0.645644 0.854458 0.356119 0.058 Uiso 1 1 calc R U . . .
C7 C 0.47711(9) 0.5776(3) 0.61013(9) 0.0457(5) Uani 1 1 d . . . . .
C59 C 0.84097(8) 0.3631(3) 0.42420(9) 0.0432(5) Uani 1 1 d . . . . .
H59 H 0.840080 0.373983 0.459366 0.052 Uiso 1 1 calc R U . . .
C98 C 0.59627(10) 0.9181(2) 0.40472(11) 0.0518(6) Uani 1 1 d . . . . .
C2 C 0.52174(8) 0.5170(3) 0.60047(9) 0.0452(5) Uani 1 1 d . . . . .
C93 C 0.57786(10) 0.4170(3) 0.44826(10) 0.0508(6) Uani 1 1 d . . . . .
H93A H 0.568332 0.462155 0.477836 0.061 Uiso 1 1 calc R U . . .
H93B H 0.564584 0.326624 0.449017 0.061 Uiso 1 1 calc R U . . .
C69 C 0.78335(10) 0.0752(3) 0.34635(12) 0.0568(7) Uani 1 1 d . . . . .
C63 C 0.92345(8) 0.2626(3) 0.41366(9) 0.0451(5) Uani 1 1 d . . . . .
C42 C 0.17192(9) 0.6960(3) 0.56619(9) 0.0464(5) Uani 1 1 d . . . . .
C97 C 0.56065(10) 0.8683(3) 0.43489(10) 0.0511(6) Uani 1 1 d . . . . .
H97 H 0.544403 0.928867 0.454756 0.061 Uiso 1 1 calc R U . . .
C87 C 0.60877(12) 0.4192(3) 0.23015(11) 0.0615(7) Uani 1 1 d . . . . .
H87 H 0.584463 0.452733 0.210171 0.074 Uiso 1 1 calc R U . . .
C13 C 0.44224(8) 0.2329(2) 0.56764(9) 0.0406(5) Uani 1 1 d . . . . .
C60 C 0.81669(8) 0.2277(3) 0.41345(9) 0.0440(5) Uani 1 1 d . . . . .
C34 C 0.20608(9) 0.3759(3) 0.55065(9) 0.0468(5) Uani 1 1 d . . . . .
H34A H 0.192331 0.286076 0.549434 0.056 Uiso 1 1 calc R U . . .
H34B H 0.197129 0.422071 0.521103 0.056 Uiso 1 1 calc R U . . .
C105 C 0.51247(9) 0.4268(3) 0.29063(10) 0.0518(6) Uani 1 1 d . . . . .
C10 C 0.54740(8) 0.2918(3) 0.57210(10) 0.0486(6) Uani 1 1 d . . . . .
C49 C 0.14003(9) 0.3957(3) 0.70706(10) 0.0519(6) Uani 1 1 d . . . . .
C84 C 0.68245(11) 0.3184(3) 0.29016(12) 0.0600(7) Uani 1 1 d . . . . .
H84 H 0.706834 0.284447 0.309966 0.072 Uiso 1 1 calc R U . . .
C43 C 0.18619(10) 0.8296(3) 0.56790(10) 0.0528(6) Uani 1 1 d . . . . .
H43 H 0.167250 0.892692 0.551765 0.063 Uiso 1 1 calc R U . . .
C40 C 0.23647(12) 0.3816(3) 0.76856(11) 0.0604(7) Uani 1 1 d . . . . .
H40 H 0.212109 0.415855 0.788303 0.072 Uiso 1 1 calc R U . . .
C37 C 0.31011(10) 0.2776(3) 0.70920(12) 0.0565(7) Uani 1 1 d . . . . .
H37 H 0.334459 0.242890 0.689523 0.068 Uiso 1 1 calc R U . . .
C18 C 0.40578(11) 0.0013(3) 0.67217(12) 0.0596(7) Uani 1 1 d . . . . .
H18 H 0.387362 -0.076008 0.676845 0.072 Uiso 1 1 calc R U . . .
C17 C 0.42812(12) 0.0587(3) 0.71200(12) 0.0634(8) Uani 1 1 d . . . . .
C6 C 0.47513(11) 0.7026(3) 0.63086(11) 0.0592(7) Uani 1 1 d . . . . .
H6 H 0.445330 0.742755 0.637403 0.071 Uiso 1 1 calc R U . . .
C47 C 0.12954(12) 0.6626(4) 0.53364(13) 0.0686(8) Uani 1 1 d . . . . .
H47A H 0.102451 0.633968 0.552913 0.103 Uiso 1 1 calc R U . . .
H47B H 0.138643 0.591672 0.511913 0.103 Uiso 1 1 calc R U . . .
H47C H 0.120593 0.740927 0.515413 0.103 Uiso 1 1 calc R U . . .
C72 C 0.83461(12) 0.2150(3) 0.27579(11) 0.0604(7) Uani 1 1 d . . . . .
H72 H 0.851178 0.264435 0.252503 0.072 Uiso 1 1 calc R U . . .
C38 C 0.31493(13) 0.2808(4) 0.75893(13) 0.0703(9) Uani 1 1 d . . . . .
H38 H 0.343325 0.248092 0.772858 0.084 Uiso 1 1 calc R U . . .
C16 C 0.45434(11) 0.1744(3) 0.70432(11) 0.0576(7) Uani 1 1 d . . . . .
H16 H 0.469476 0.216643 0.730248 0.069 Uiso 1 1 calc R U . . .
C12 C 0.47758(9) 0.1500(3) 0.53655(10) 0.0505(6) Uani 1 1 d . . . . .
H12A H 0.466879 0.057095 0.535754 0.061 Uiso 1 1 calc R U . . .
H12B H 0.477229 0.184136 0.503722 0.061 Uiso 1 1 calc R U . . .
C8 C 0.43547(8) 0.4870(2) 0.59459(9) 0.0427(5) Uani 1 1 d . . . . .
H8 H 0.421011 0.445620 0.623327 0.051 Uiso 1 1 calc R U . . .
C70 C 0.78408(12) 0.0352(3) 0.29820(14) 0.0693(9) Uani 1 1 d . . . . .
H70 H 0.766114 -0.040212 0.289528 0.083 Uiso 1 1 calc R U . . .
C44 C 0.22708(10) 0.8746(3) 0.59230(10) 0.0518(6) Uani 1 1 d . . . . .
C61 C 0.84860(9) 0.1235(3) 0.43942(10) 0.0511(6) Uani 1 1 d . . . . .
H61A H 0.847990 0.140955 0.473885 0.061 Uiso 1 1 calc R U . . .
H61B H 0.835364 0.034328 0.434039 0.061 Uiso 1 1 calc R U . . .
C58 C 0.81788(9) 0.4906(3) 0.40290(10) 0.0463(5) Uani 1 1 d . . . . .
H58 H 0.797336 0.467960 0.375156 0.056 Uiso 1 1 calc R U . . .
C57 C 0.86134(10) 0.5725(3) 0.38689(9) 0.0485(6) Uani 1 1 d . . . . .
C3 C 0.56493(10) 0.5812(3) 0.61221(12) 0.0605(7) Uani 1 1 d . . . . .
H3 H 0.594797 0.540697 0.606292 0.073 Uiso 1 1 calc R U . . .
C11 C 0.52921(9) 0.1564(3) 0.55631(11) 0.0553(7) Uani 1 1 d . . . . .
H11A H 0.531309 0.095759 0.583674 0.066 Uiso 1 1 calc R U . . .
H11B H 0.551021 0.122521 0.531633 0.066 Uiso 1 1 calc R U . . .
C71 C 0.80982(13) 0.1007(3) 0.26259(12) 0.0664(8) Uani 1 1 d . . . . .
C62 C 0.90069(9) 0.1275(3) 0.42171(11) 0.0505(6) Uani 1 1 d . . . . .
H62A H 0.920559 0.079217 0.444866 0.061 Uiso 1 1 calc R U . . .
H62B H 0.902221 0.078250 0.391504 0.061 Uiso 1 1 calc R U . . .
C86 C 0.65127(13) 0.3676(4) 0.21070(13) 0.0729(9) Uani 1 1 d . . . . .
H86 H 0.655534 0.366131 0.177376 0.087 Uiso 1 1 calc R U . . .
C92 C 0.63314(10) 0.4093(3) 0.44579(10) 0.0550(6) Uani 1 1 d . . . . .
H92A H 0.646143 0.494426 0.457057 0.066 Uiso 1 1 calc R U . . .
H92B H 0.643869 0.340488 0.468212 0.066 Uiso 1 1 calc R U . . .
C56 C 0.90411(9) 0.4997(3) 0.39310(10) 0.0487(6) Uani 1 1 d . . . . .
C39 C 0.27890(14) 0.3309(4) 0.78846(12) 0.0721(9) Uani 1 1 d . . . . .
H39 H 0.283073 0.330720 0.821793 0.087 Uiso 1 1 calc R U . . .
C101 C 0.50876(12) 0.6967(4) 0.47397(12) 0.0663(8) Uani 1 1 d . . . . .
H10A H 0.481311 0.658648 0.457512 0.099 Uiso 1 1 calc R U . . .
H10B H 0.498791 0.775906 0.491154 0.099 Uiso 1 1 calc R U . . .
H10C H 0.521602 0.632142 0.496384 0.099 Uiso 1 1 calc R U . . .
C67 C 0.86313(13) 0.7017(3) 0.36803(11) 0.0618(7) Uani 1 1 d . . . . .
H67 H 0.834739 0.750589 0.363263 0.074 Uiso 1 1 calc R U . . .
C65 C 0.95000(13) 0.6837(3) 0.36329(14) 0.0726(9) Uani 1 1 d . . . . .
H65 H 0.979741 0.722606 0.355649 0.087 Uiso 1 1 calc R U . . .
C64 C 0.94898(11) 0.5542(3) 0.38124(12) 0.0634(7) Uani 1 1 d . . . . .
H64 H 0.977444 0.505088 0.385263 0.076 Uiso 1 1 calc R U . . .
C85 C 0.68704(12) 0.3188(4) 0.24033(14) 0.0725(9) Uani 1 1 d . . . . .
H85 H 0.715308 0.284808 0.226547 0.087 Uiso 1 1 calc R U . . .
C20 C 0.38371(13) -0.0238(3) 0.58572(16) 0.0758(9) Uani 1 1 d . . . . .
H20A H 0.407313 -0.058108 0.563359 0.114 Uiso 1 1 calc R U . . .
H20B H 0.361835 0.035465 0.569091 0.114 Uiso 1 1 calc R U . . .
H20C H 0.365756 -0.097234 0.599440 0.114 Uiso 1 1 calc R U . . .
C78 C 0.72745(13) 0.7233(4) 0.45395(15) 0.0748(9) Uani 1 1 d . . . . .
H78A H 0.703808 0.774802 0.436387 0.112 Uiso 1 1 calc R U . . .
H78B H 0.747625 0.782940 0.472440 0.112 Uiso 1 1 calc R U . . .
H78C H 0.711160 0.662067 0.475305 0.112 Uiso 1 1 calc R U . . .
C66 C 0.90795(15) 0.7567(3) 0.35640(13) 0.0738(9) Uani 1 1 d . . . . .
H66 H 0.909652 0.843432 0.343878 0.089 Uiso 1 1 calc R U . . .
C48 C 0.24070(15) 1.0205(3) 0.59246(14) 0.0766(9) Uani 1 1 d . . . . .
H48A H 0.263995 1.036832 0.617590 0.115 Uiso 1 1 calc R U . . .
H48B H 0.212243 1.074049 0.598096 0.115 Uiso 1 1 calc R U . . .
H48C H 0.254591 1.044042 0.561799 0.115 Uiso 1 1 calc R U . . .
C26 C 0.37516(14) 0.6850(4) 0.49852(13) 0.0735(9) Uani 1 1 d . . . . .
H26A H 0.377675 0.671760 0.464264 0.110 Uiso 1 1 calc R U . . .
H26B H 0.383745 0.776047 0.506312 0.110 Uiso 1 1 calc R U . . .
H26C H 0.342411 0.667767 0.508706 0.110 Uiso 1 1 calc R U . . .
C74 C 0.75283(14) -0.0066(4) 0.38040(18) 0.0868(11) Uani 1 1 d . . . . .
H74A H 0.741021 -0.085186 0.364012 0.130 Uiso 1 1 calc R U . . .
H74B H 0.725829 0.046436 0.391304 0.130 Uiso 1 1 calc R U . . .
H74C H 0.772127 -0.033337 0.407641 0.130 Uiso 1 1 calc R U . . .
C102 C 0.60787(16) 1.0653(3) 0.40321(18) 0.0854(11) Uani 1 1 d . . . . .
H10D H 0.631471 1.085929 0.427644 0.128 Uiso 1 1 calc R U . . .
H10E H 0.578823 1.116260 0.409002 0.128 Uiso 1 1 calc R U . . .
H10F H 0.620741 1.088011 0.372035 0.128 Uiso 1 1 calc R U . . .
C5 C 0.51796(13) 0.7683(3) 0.64195(14) 0.0721(8) Uani 1 1 d . . . . .
H5 H 0.517096 0.853918 0.655501 0.086 Uiso 1 1 calc R U . . .
C21 C 0.42424(19) -0.0048(4) 0.76147(16) 0.0961(13) Uani 1 1 d . . . . .
H21A H 0.391298 -0.032221 0.767134 0.144 Uiso 1 1 calc R U . . .
H21B H 0.433770 0.059420 0.785585 0.144 Uiso 1 1 calc R U . . .
H21C H 0.445206 -0.081813 0.763101 0.144 Uiso 1 1 calc R U . . .
C4 C 0.56208(13) 0.7068(4) 0.63290(14) 0.0742(9) Uani 1 1 d . . . . .
H4 H 0.590607 0.751602 0.641010 0.089 Uiso 1 1 calc R U . . .
C75 C 0.8107(2) 0.0480(5) 0.21149(16) 0.1058(16) Uani 1 1 d . . . . .
H75A H 0.817918 0.120395 0.189665 0.159 Uiso 1 1 calc R U . . .
H75B H 0.779583 0.010439 0.203622 0.159 Uiso 1 1 calc R U . . .
H75C H 0.835214 -0.020236 0.208664 0.159 Uiso 1 1 calc R U . . .
C107 C 0.44317(16) 0.4975(5) 0.2475(2) 0.1083(17) Uani 1 1 d . . . . .
H10G H 0.447674 0.438229 0.220529 0.162 Uiso 1 1 calc R U . . .
H10H H 0.428215 0.579416 0.236719 0.162 Uiso 1 1 calc R U . . .
H10I H 0.422683 0.454953 0.271057 0.162 Uiso 1 1 calc R U . . .
C51 C 0.06939(14) 0.4797(5) 0.74458(19) 0.0995(14) Uani 1 1 d . . . . .
H51A H 0.048524 0.444682 0.719801 0.149 Uiso 1 1 calc R U . . .
H51B H 0.056568 0.563554 0.756144 0.149 Uiso 1 1 calc R U . . .
H51C H 0.071158 0.416664 0.770781 0.149 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
O22 C13 1.425(3) . ?
O53 C36 1.228(3) . ?
O54 C33 1.423(3) . ?
O25 C24 1.320(4) . ?
O25 C26 1.450(3) . ?
O80 C63 1.230(3) . ?
N82 C91 1.350(3) . ?
N82 C83 1.423(3) . ?
N82 C90 1.481(3) . ?
N28 C36 1.355(3) . ?
N28 C29 1.419(3) . ?
N28 C32 1.482(3) . ?
O103 C94 1.422(3) . ?
O50 C49 1.322(4) . ?
O50 C51 1.434(4) . ?
O81 C60 1.422(3) . ?
O77 C76 1.318(3) . ?
O77 C78 1.439(4) . ?
O23 C10 1.232(3) . ?
O104 C91 1.224(3) . ?
N1 C10 1.351(3) . ?
N1 C2 1.415(3) . ?
N1 C9 1.495(3) . ?
O106 C105 1.323(4) . ?
O106 C107 1.450(4) . ?
C95 C100 1.397(3) . ?
C95 C96 1.413(3) . ?
C95 C94 1.529(3) . ?
C29 C37 1.386(4) . ?
C29 C30 1.388(4) . ?
O79 C76 1.188(4) . ?
C36 C35 1.501(4) . ?
C68 C73 1.386(4) . ?
C68 C69 1.412(4) . ?
C68 C60 1.539(4) . ?
C90 C94 1.534(3) . ?
C90 C89 1.537(3) . ?
O27 C24 1.189(3) . ?
N55 C63 1.356(3) . ?
N55 C56 1.413(4) . ?
N55 C59 1.484(3) . ?
C14 C15 1.398(4) . ?
C14 C19 1.414(4) . ?
C14 C13 1.530(4) . ?
C32 C33 1.535(3) . ?
C32 C31 1.535(3) . ?
C96 C97 1.390(4) . ?
C96 C101 1.513(4) . ?
O108 C105 1.194(4) . ?
C46 C45 1.379(4) . ?
C46 C41 1.393(3) . ?
O52 C49 1.188(4) . ?
C83 C88 1.387(4) . ?
C83 C84 1.386(4) . ?
C94 C93 1.539(4) . ?
C35 C34 1.520(4) . ?
C45 C44 1.375(4) . ?
C33 C41 1.527(3) . ?
C33 C34 1.537(4) . ?
C41 C42 1.410(3) . ?
C88 C87 1.383(4) . ?
C88 C89 1.516(4) . ?
C73 C72 1.389(4) . ?
C24 C8 1.507(3) . ?
C100 C99 1.374(4) . ?
C30 C40 1.375(4) . ?
C30 C31 1.517(4) . ?
C15 C16 1.382(4) . ?
C76 C58 1.518(4) . ?
C91 C92 1.504(4) . ?
C89 C105 1.514(3) . ?
C19 C18 1.390(4) . ?
C19 C20 1.516(5) . ?
C31 C49 1.518(3) . ?
C9 C13 1.534(3) . ?
C9 C8 1.547(3) . ?
C99 C98 1.386(4) . ?
C7 C6 1.369(4) . ?
C7 C2 1.394(3) . ?
C7 C8 1.520(4) . ?
C59 C60 1.531(4) . ?
C59 C58 1.536(3) . ?
C98 C97 1.380(4) . ?
C98 C102 1.498(4) . ?
C2 C3 1.388(4) . ?
C93 C92 1.525(4) . ?
C69 C70 1.391(5) . ?
C69 C74 1.502(5) . ?
C63 C62 1.498(4) . ?
C42 C43 1.386(4) . ?
C42 C47 1.511(4) . ?
C87 C86 1.386(5) . ?
C13 C12 1.538(3) . ?
C60 C61 1.537(3) . ?
C10 C11 1.501(4) . ?
C84 C85 1.385(5) . ?
C43 C44 1.387(4) . ?
C40 C39 1.386(5) . ?
C37 C38 1.384(5) . ?
C18 C17 1.385(5) . ?
C17 C16 1.375(5) . ?
C17 C21 1.512(5) . ?
C6 C5 1.383(5) . ?
C72 C71 1.374(5) . ?
C38 C39 1.378(6) . ?
C12 C11 1.524(4) . ?
C70 C71 1.378(5) . ?
C44 C48 1.498(4) . ?
C61 C62 1.516(3) . ?
C58 C57 1.513(4) . ?
C57 C67 1.387(4) . ?
C57 C56 1.393(4) . ?
C3 C4 1.376(5) . ?
C71 C75 1.509(5) . ?
C86 C85 1.371(6) . ?
C56 C64 1.388(4) . ?
C67 C66 1.388(5) . ?
C65 C66 1.380(5) . ?
C65 C64 1.380(5) . ?
C5 C4 1.383(5) . ?

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
C24 O25 C26 115.6(2) . . ?
C91 N82 C83 126.4(2) . . ?
C91 N82 C90 124.9(2) . . ?
C83 N82 C90 108.58(18) . . ?
C36 N28 C29 126.86(19) . . ?
C36 N28 C32 124.5(2) . . ?
C29 N28 C32 108.57(18) . . ?
C49 O50 C51 117.6(3) . . ?
C76 O77 C78 115.0(3) . . ?
C10 N1 C2 127.0(2) . . ?
C10 N1 C9 123.9(2) . . ?
C2 N1 C9 109.11(18) . . ?
C105 O106 C107 116.4(3) . . ?
C100 C95 C96 117.5(2) . . ?
C100 C95 C94 121.0(2) . . ?
C96 C95 C94 121.5(2) . . ?
C37 C29 C30 121.7(3) . . ?
C37 C29 N28 129.0(2) . . ?
C30 C29 N28 109.3(2) . . ?
O53 C36 N28 120.9(2) . . ?
O53 C36 C35 121.8(2) . . ?
N28 C36 C35 117.3(2) . . ?
C73 C68 C69 117.2(3) . . ?
C73 C68 C60 121.6(2) . . ?
C69 C68 C60 120.9(2) . . ?
N82 C90 C94 114.38(18) . . ?
N82 C90 C89 104.61(18) . . ?
C94 C90 C89 118.10(19) . . ?
C63 N55 C56 127.4(2) . . ?
C63 N55 C59 123.0(2) . . ?
C56 N55 C59 109.63(19) . . ?
C15 C14 C19 116.7(3) . . ?
C15 C14 C13 121.7(2) . . ?
C19 C14 C13 121.6(2) . . ?
N28 C32 C33 115.09(18) . . ?
N28 C32 C31 104.32(18) . . ?
C33 C32 C31 117.37(19) . . ?
C97 C96 C95 118.1(2) . . ?
C97 C96 C101 116.9(2) . . ?
C95 C96 C101 125.1(2) . . ?
C45 C46 C41 122.7(2) . . ?
C88 C83 C84 121.8(3) . . ?
C88 C83 N82 109.1(2) . . ?
C84 C83 N82 129.2(2) . . ?
O103 C94 C95 107.05(18) . . ?
O103 C94 C90 105.20(19) . . ?
C95 C94 C90 116.49(19) . . ?
O103 C94 C93 111.7(2) . . ?
C95 C94 C93 110.8(2) . . ?
C90 C94 C93 105.50(19) . . ?
C36 C35 C34 117.0(2) . . ?
C44 C45 C46 120.8(2) . . ?
O54 C33 C41 107.30(17) . . ?
O54 C33 C32 104.69(18) . . ?
C41 C33 C32 115.97(18) . . ?
O54 C33 C34 112.12(19) . . ?
C41 C33 C34 111.02(19) . . ?
C32 C33 C34 105.67(18) . . ?
C46 C41 C42 117.0(2) . . ?
C46 C41 C33 120.8(2) . . ?
C42 C41 C33 122.1(2) . . ?
C87 C88 C83 119.9(3) . . ?
C87 C88 C89 129.4(2) . . ?
C83 C88 C89 110.7(2) . . ?
C68 C73 C72 122.6(3) . . ?
O27 C24 O25 122.9(2) . . ?
O27 C24 C8 123.3(3) . . ?
O25 C24 C8 113.7(2) . . ?
C99 C100 C95 122.4(2) . . ?
C40 C30 C29 120.1(3) . . ?
C40 C30 C31 129.6(2) . . ?
C29 C30 C31 110.2(2) . . ?
C16 C15 C14 122.7(3) . . ?
O79 C76 O77 123.5(3) . . ?
O79 C76 C58 124.9(3) . . ?
O77 C76 C58 111.5(2) . . ?
O104 C91 N82 121.1(3) . . ?
O104 C91 C92 121.3(2) . . ?
N82 C91 C92 117.6(2) . . ?
C105 C89 C88 112.2(2) . . ?
C105 C89 C90 113.1(2) . . ?
C88 C89 C90 101.96(18) . . ?
C18 C19 C14 118.9(3) . . ?
C18 C19 C20 117.3(3) . . ?
C14 C19 C20 123.9(3) . . ?
C30 C31 C49 112.9(2) . . ?
C30 C31 C32 102.04(18) . . ?
C49 C31 C32 112.1(2) . . ?
N1 C9 C13 113.83(17) . . ?
N1 C9 C8 104.80(19) . . ?
C13 C9 C8 117.98(19) . . ?
C100 C99 C98 120.8(2) . . ?
C6 C7 C2 120.5(3) . . ?
C6 C7 C8 128.8(2) . . ?
C2 C7 C8 110.7(2) . . ?
N55 C59 C60 114.03(19) . . ?
N55 C59 C58 105.3(2) . . ?
C60 C59 C58 118.0(2) . . ?
C97 C98 C99 116.8(2) . . ?
C97 C98 C102 121.2(3) . . ?
C99 C98 C102 122.0(3) . . ?
C3 C2 C7 120.7(3) . . ?
C3 C2 N1 129.6(2) . . ?
C7 C2 N1 109.6(2) . . ?
C92 C93 C94 111.5(2) . . ?
C70 C69 C68 118.5(3) . . ?
C70 C69 C74 117.1(3) . . ?
C68 C69 C74 124.5(3) . . ?
O80 C63 N55 122.2(2) . . ?
O80 C63 C62 120.7(2) . . ?
N55 C63 C62 116.9(2) . . ?
C43 C42 C41 118.7(2) . . ?
C43 C42 C47 116.7(2) . . ?
C41 C42 C47 124.5(2) . . ?
C98 C97 C96 124.2(2) . . ?
C88 C87 C86 118.8(3) . . ?
O22 C13 C14 112.18(19) . . ?
O22 C13 C9 104.37(18) . . ?
C14 C13 C9 116.9(2) . . ?
O22 C13 C12 106.63(19) . . ?
C14 C13 C12 111.4(2) . . ?
C9 C13 C12 104.5(2) . . ?
O81 C60 C59 105.7(2) . . ?
O81 C60 C61 105.94(19) . . ?
C59 C60 C61 104.6(2) . . ?
O81 C60 C68 112.8(2) . . ?
C59 C60 C68 116.9(2) . . ?
C61 C60 C68 110.1(2) . . ?
C35 C34 C33 112.1(2) . . ?
O108 C105 O106 125.2(3) . . ?
O108 C105 C89 124.4(3) . . ?
O106 C105 C89 110.4(2) . . ?
O23 C10 N1 121.8(3) . . ?
O23 C10 C11 120.8(2) . . ?
N1 C10 C11 117.4(2) . . ?
O52 C49 O50 124.5(3) . . ?
O52 C49 C31 124.8(3) . . ?
O50 C49 C31 110.8(2) . . ?
C85 C84 C83 117.0(3) . . ?
C42 C43 C44 123.8(2) . . ?
C30 C40 C39 119.0(3) . . ?
C38 C37 C29 117.1(3) . . ?
C17 C18 C19 123.7(3) . . ?
C16 C17 C18 117.0(3) . . ?
C16 C17 C21 121.8(4) . . ?
C18 C17 C21 121.2(3) . . ?
C7 C6 C5 119.2(3) . . ?
C71 C72 C73 120.5(3) . . ?
C39 C38 C37 122.0(3) . . ?
C17 C16 C15 120.9(3) . . ?
C11 C12 C13 111.5(2) . . ?
C24 C8 C7 110.4(2) . . ?
C24 C8 C9 116.7(2) . . ?
C7 C8 C9 102.40(18) . . ?
C71 C70 C69 123.9(3) . . ?
C45 C44 C43 116.9(2) . . ?
C45 C44 C48 122.0(3) . . ?
C43 C44 C48 121.1(3) . . ?
C62 C61 C60 111.8(2) . . ?
C57 C58 C76 110.4(2) . . ?
C57 C58 C59 103.2(2) . . ?
C76 C58 C59 111.5(2) . . ?
C67 C57 C56 119.8(3) . . ?
C67 C57 C58 129.5(3) . . ?
C56 C57 C58 110.7(2) . . ?
C4 C3 C2 117.8(3) . . ?
C10 C11 C12 116.9(2) . . ?
C72 C71 C70 117.1(3) . . ?
C72 C71 C75 121.9(4) . . ?
C70 C71 C75 121.0(3) . . ?
C63 C62 C61 117.8(2) . . ?
C85 C86 C87 120.3(3) . . ?
C91 C92 C93 116.9(2) . . ?
C64 C56 C57 121.3(3) . . ?
C64 C56 N55 129.1(3) . . ?
C57 C56 N55 109.5(2) . . ?
C38 C39 C40 120.1(3) . . ?
C57 C67 C66 119.0(3) . . ?
C66 C65 C64 121.6(3) . . ?
C65 C64 C56 117.9(3) . . ?
C86 C85 C84 122.1(3) . . ?
C65 C66 C67 120.4(3) . . ?
C6 C5 C4 120.0(3) . . ?
C3 C4 C5 121.8(3) . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.027

