# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_221108_wt_s1
_database_code_depnum_ccdc_archive 'CCDC 2261237'
loop_
_audit_author_name
_audit_author_address
'Wen-Tao Wang'
;Zhejiang University
China
;
_audit_update_record             
;
2023-05-07 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2022-11-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.2814(6)
_cell_length_b                   9.8263(5)
_cell_length_c                   9.7772(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.082(2)
_cell_angle_gamma                90
_cell_volume                     1466.02(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4989
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1752 before and 0.0671 after correction.
The Ratio of minimum to maximum transmission is 0.9182.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16830
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.109
_diffrn_reflns_theta_min         2.465
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2503
_reflns_number_total             3239
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+0.4449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C3, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41319(7) 0.48345(12) 0.41529(11) 0.0422(3) Uani 1 1 d . . . . .
O2 O 0.34244(7) 0.17216(11) 0.34209(11) 0.0396(3) Uani 1 1 d . . . . .
O3 O 0.38906(7) 0.55600(11) 0.10098(11) 0.0419(3) Uani 1 1 d . . . . .
N1 N 0.14804(8) 0.50966(13) 0.37246(12) 0.0326(3) Uani 1 1 d . . . . .
N2 N 0.28360(7) 0.43968(12) 0.29907(11) 0.0273(3) Uani 1 1 d . . . . .
N3 N 0.33284(7) 0.36718(12) 0.20828(11) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.32207(12) 0.61491(17) 0.63212(16) 0.0455(4) Uani 1 1 d . . . . .
H1 H 0.384057 0.613870 0.646376 0.055 Uiso 1 1 calc R U . . .
C2 C 0.27034(14) 0.66940(18) 0.72930(17) 0.0546(4) Uani 1 1 d . U . . .
H2 H 0.296727 0.705161 0.811846 0.066 Uiso 1 1 calc R U . . .
C3 C 0.18008(14) 0.67240(18) 0.70747(17) 0.0540(4) Uani 1 1 d . U . . .
H3 H 0.145236 0.710234 0.775532 0.065 Uiso 1 1 calc R U . . .
C4 C 0.14005(12) 0.62161(17) 0.58909(16) 0.0446(4) Uani 1 1 d . . . . .
H4 H 0.078112 0.625623 0.574998 0.053 Uiso 1 1 calc R U . . .
C5 C 0.19102(10) 0.56381(15) 0.48912(14) 0.0337(3) Uani 1 1 d . . . . .
C6 C 0.28179(10) 0.56090(14) 0.51163(14) 0.0339(3) Uani 1 1 d . . . . .
C7 C 0.33387(9) 0.49541(14) 0.41043(14) 0.0313(3) Uani 1 1 d . . . . .
C8 C 0.19241(8) 0.44963(14) 0.28175(14) 0.0275(3) Uani 1 1 d . . . . .
C9 C 0.37054(9) 0.24144(15) 0.25327(14) 0.0312(3) Uani 1 1 d . . . . .
C10 C 0.44736(9) 0.22163(17) 0.16943(15) 0.0367(3) Uani 1 1 d . . . . .
H10 H 0.481308 0.140828 0.165999 0.044 Uiso 1 1 calc R U . . .
C11 C 0.46116(9) 0.33458(17) 0.10001(15) 0.0369(3) Uani 1 1 d . . . . .
H11 H 0.507068 0.347519 0.039529 0.044 Uiso 1 1 calc R U . . .
C12 C 0.39428(9) 0.43787(15) 0.13075(14) 0.0315(3) Uani 1 1 d . . . . .
C13 C 0.14406(9) 0.39269(16) 0.15303(14) 0.0331(3) Uani 1 1 d . . . . .
C14 C 0.04590(10) 0.4124(2) 0.16736(18) 0.0578(5) Uani 1 1 d . . . . .
H14A H 0.027515 0.361388 0.247037 0.087 Uiso 1 1 calc R U . . .
H14B H 0.013754 0.379088 0.084594 0.087 Uiso 1 1 calc R U . . .
H14C H 0.033405 0.509302 0.179649 0.087 Uiso 1 1 calc R U . . .
C15 C 0.17094(11) 0.47142(19) 0.02651(15) 0.0431(4) Uani 1 1 d . . . . .
H15A H 0.161981 0.569042 0.040791 0.065 Uiso 1 1 calc R U . . .
H15B H 0.135108 0.441342 -0.053992 0.065 Uiso 1 1 calc R U . . .
H15C H 0.232909 0.454195 0.011897 0.065 Uiso 1 1 calc R U . . .
C16 C 0.16051(13) 0.23996(19) 0.1335(2) 0.0546(5) Uani 1 1 d . . . . .
H16A H 0.219435 0.226330 0.101043 0.082 Uiso 1 1 calc R U . . .
H16B H 0.117001 0.203280 0.066049 0.082 Uiso 1 1 calc R U . . .
H16C H 0.155613 0.192783 0.221110 0.082 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2161(17) . ?
O2 C9 1.2009(17) . ?
O3 C12 1.1984(18) . ?
N1 C5 1.3910(19) . ?
N1 C8 1.2880(17) . ?
N2 N3 1.3905(15) . ?
N2 C7 1.4090(18) . ?
N2 C8 1.3982(17) . ?
N3 C9 1.4230(18) . ?
N3 C12 1.4196(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(2) . ?
C1 C6 1.404(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(2) . ?
C5 C6 1.393(2) . ?
C6 C7 1.453(2) . ?
C8 C13 1.5307(19) . ?
C9 C10 1.480(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.324(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.483(2) . ?
C13 C14 1.526(2) . ?
C13 C15 1.534(2) . ?
C13 C16 1.535(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C5 119.81(12) . . ?
N3 N2 C7 113.65(10) . . ?
N3 N2 C8 121.90(11) . . ?
C8 N2 C7 124.40(11) . . ?
N2 N3 C9 118.13(11) . . ?
N2 N3 C12 119.10(11) . . ?
C12 N3 C9 108.75(11) . . ?
C2 C1 H1 120.5 . . ?
C2 C1 C6 118.95(17) . . ?
C6 C1 H1 120.5 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.41(16) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.12(16) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.72(17) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 118.11(14) . . ?
N1 C5 C6 122.95(13) . . ?
C6 C5 C4 118.93(14) . . ?
C1 C6 C7 120.49(15) . . ?
C5 C6 C1 120.86(14) . . ?
C5 C6 C7 118.60(13) . . ?
O1 C7 N2 119.57(13) . . ?
O1 C7 C6 126.69(13) . . ?
N2 C7 C6 113.73(12) . . ?
N1 C8 N2 120.45(12) . . ?
N1 C8 C13 119.00(12) . . ?
N2 C8 C13 120.53(11) . . ?
O2 C9 N3 124.13(13) . . ?
O2 C9 C10 130.62(14) . . ?
N3 C9 C10 105.25(12) . . ?
C9 C10 H10 125.5 . . ?
C11 C10 C9 109.07(13) . . ?
C11 C10 H10 125.5 . . ?
C10 C11 H11 125.1 . . ?
C10 C11 C12 109.84(13) . . ?
C12 C11 H11 125.1 . . ?
O3 C12 N3 124.50(13) . . ?
O3 C12 C11 130.66(13) . . ?
N3 C12 C11 104.85(12) . . ?
C8 C13 C15 109.90(12) . . ?
C8 C13 C16 112.60(12) . . ?
C14 C13 C8 108.15(12) . . ?
C14 C13 C15 108.50(13) . . ?
C14 C13 C16 107.68(15) . . ?
C15 C13 C16 109.89(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C9 C10 C11 -169.95(15) . . . . ?
N1 C5 C6 C1 -178.93(14) . . . . ?
N1 C5 C6 C7 -1.6(2) . . . . ?
N1 C8 C13 C14 -4.39(19) . . . . ?
N1 C8 C13 C15 113.90(15) . . . . ?
N1 C8 C13 C16 -123.24(15) . . . . ?
N2 N3 C9 O2 24.80(19) . . . . ?
N2 N3 C9 C10 -154.71(11) . . . . ?
N2 N3 C12 O3 -25.9(2) . . . . ?
N2 N3 C12 C11 153.84(11) . . . . ?
N2 C8 C13 C14 177.19(14) . . . . ?
N2 C8 C13 C15 -64.52(17) . . . . ?
N2 C8 C13 C16 58.34(18) . . . . ?
N3 N2 C7 O1 3.89(18) . . . . ?
N3 N2 C7 C6 -174.87(11) . . . . ?
N3 N2 C8 N1 175.28(12) . . . . ?
N3 N2 C8 C13 -6.33(19) . . . . ?
N3 C9 C10 C11 9.51(16) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C7 O1 -2.1(2) . . . . ?
C1 C6 C7 N2 176.59(13) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C2 C1 C6 C7 -176.38(14) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 N1 178.06(15) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C7 177.28(13) . . . . ?
C5 N1 C8 N2 -0.6(2) . . . . ?
C5 N1 C8 C13 -179.05(13) . . . . ?
C5 C6 C7 O1 -179.43(14) . . . . ?
C5 C6 C7 N2 -0.77(19) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C7 N2 N3 C9 69.30(15) . . . . ?
C7 N2 N3 C12 -66.32(15) . . . . ?
C7 N2 C8 N1 -1.9(2) . . . . ?
C7 N2 C8 C13 176.48(13) . . . . ?
C8 N1 C5 C4 -176.50(14) . . . . ?
C8 N1 C5 C6 2.4(2) . . . . ?
C8 N2 N3 C9 -108.17(14) . . . . ?
C8 N2 N3 C12 116.21(14) . . . . ?
C8 N2 C7 O1 -178.71(13) . . . . ?
C8 N2 C7 C6 2.52(19) . . . . ?
C9 N3 C12 O3 -165.24(14) . . . . ?
C9 N3 C12 C11 14.48(14) . . . . ?
C9 C10 C11 C12 -0.61(17) . . . . ?
C10 C11 C12 O3 171.18(16) . . . . ?
C10 C11 C12 N3 -8.52(16) . . . . ?
C12 N3 C9 O2 164.60(14) . . . . ?
C12 N3 C9 C10 -14.91(14) . . . . ?

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

data_cu_230104_tp_red_0m
_database_code_depnum_ccdc_archive 'CCDC 2261240'
loop_
_audit_author_name
_audit_author_address
'Wen-Tao Wang'
;Zhejiang University
China
;
_audit_update_record             
;
2023-05-07 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-01-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H28 N4 O5'
_chemical_formula_sum            'C27 H28 N4 O5'
_chemical_formula_weight         488.53
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5810(2)
_cell_length_b                   13.3130(3)
_cell_length_c                   10.2528(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.0290(10)
_cell_angle_gamma                90
_cell_volume                     1220.66(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.776
_shelx_estimated_absorpt_T_min   0.711
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1479 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.8486.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18538
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         4.620
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4398
_reflns_number_total             4443
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 2054 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.0843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0751
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N4-H4
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4A), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.01182(15) 0.59159(11) 0.80476(16) 0.0353(3) Uani 1 1 d . . . . .
O2 O 0.06307(15) 0.58485(11) 0.50425(14) 0.0352(3) Uani 1 1 d . . . . .
O3 O 0.31925(14) 0.46908(10) 0.93979(12) 0.0293(3) Uani 1 1 d . . . . .
O4 O 0.25368(17) 0.15705(11) 0.78028(15) 0.0380(3) Uani 1 1 d . . . . .
O5 O 0.31550(15) 0.15129(11) 0.58938(15) 0.0366(3) Uani 1 1 d . . . . .
N1 N 0.31436(17) 0.80746(12) 0.80852(16) 0.0276(3) Uani 1 1 d . . . . .
N2 N 0.22650(16) 0.64234(11) 0.77524(15) 0.0252(3) Uani 1 1 d . . . . .
N3 N 0.22827(17) 0.54608(11) 0.72379(16) 0.0252(3) Uani 1 1 d . . . . .
N4 N 0.33946(19) 0.35402(13) 0.57397(16) 0.0296(3) Uani 1 1 d D . . . .
C1 C -0.0196(2) 0.78883(16) 0.9117(2) 0.0320(4) Uani 1 1 d . . . . .
H1 H -0.090730 0.740640 0.916422 0.038 Uiso 1 1 calc R U . . .
C2 C -0.0257(2) 0.88561(17) 0.9556(2) 0.0377(4) Uani 1 1 d . . . . .
H2 H -0.100607 0.904191 0.991653 0.045 Uiso 1 1 calc R U . . .
C3 C 0.0780(2) 0.95684(16) 0.9475(2) 0.0374(4) Uani 1 1 d . . . . .
H3 H 0.072831 1.023737 0.977643 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1881(2) 0.93096(15) 0.8960(2) 0.0328(4) Uani 1 1 d . . . . .
H4A H 0.257320 0.980063 0.889662 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1972(2) 0.83190(14) 0.85315(18) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.0915(2) 0.76131(14) 0.85993(18) 0.0262(4) Uani 1 1 d . . . . .
C7 C 0.10046(19) 0.65968(15) 0.81353(18) 0.0272(4) Uani 1 1 d . . . . .
C8 C 0.33012(19) 0.71679(13) 0.77340(17) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.1251(2) 0.52280(14) 0.58989(19) 0.0269(4) Uani 1 1 d . . . . .
C10 C 0.1115(2) 0.40939(14) 0.57892(19) 0.0285(4) Uani 1 1 d . . . . .
H10 H 0.004954 0.387613 0.551862 0.034 Uiso 1 1 calc R U . . .
C11 C 0.20712(19) 0.37030(13) 0.72602(18) 0.0244(4) Uani 1 1 d . . . . .
H11 H 0.146743 0.326098 0.764467 0.029 Uiso 1 1 calc R U . . .
C12 C 0.26020(18) 0.46318(13) 0.81538(18) 0.0239(3) Uani 1 1 d . . . . .
C13 C 0.33603(19) 0.31010(13) 0.70313(17) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.1837(2) 0.36462(16) 0.4805(2) 0.0372(4) Uani 1 1 d . . . . .
H14A H 0.139125 0.298803 0.442986 0.045 Uiso 1 1 calc R U . . .
H14B H 0.174423 0.410550 0.401853 0.045 Uiso 1 1 calc R U . . .
C15 C 0.29411(19) 0.19745(14) 0.69526(19) 0.0276(4) Uani 1 1 d . . . . .
C16 C 0.2991(3) 0.04235(17) 0.5864(3) 0.0515(6) Uani 1 1 d . . . . .
H16A H 0.296234 0.016668 0.495852 0.077 Uiso 1 1 calc R U . . .
H16B H 0.205996 0.024615 0.599987 0.077 Uiso 1 1 calc R U . . .
H16C H 0.384033 0.012538 0.661197 0.077 Uiso 1 1 calc R U . . .
H4 H 0.388(3) 0.314(2) 0.537(3) 0.062 Uiso 1 1 d D U . . .
C17 C 0.48909(19) 0.32106(14) 0.82269(18) 0.0275(4) Uani 1 1 d . . . . .
H17A H 0.515904 0.393161 0.835082 0.033 Uiso 1 1 calc R U . . .
H17B H 0.479932 0.296763 0.910525 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6136(2) 0.26438(15) 0.79811(18) 0.0282(4) Uani 1 1 d . . . . .
C19 C 0.7054(2) 0.31165(18) 0.7391(2) 0.0383(4) Uani 1 1 d . . . . .
H19 H 0.689897 0.380387 0.712991 0.046 Uiso 1 1 calc R U . . .
C20 C 0.8207(2) 0.2582(2) 0.7181(2) 0.0493(6) Uani 1 1 d . . . . .
H20 H 0.883042 0.290990 0.677126 0.059 Uiso 1 1 calc R U . . .
C21 C 0.8457(2) 0.1587(2) 0.7557(2) 0.0477(6) Uani 1 1 d . . . . .
H21 H 0.924981 0.123007 0.741559 0.057 Uiso 1 1 calc R U . . .
C22 C 0.7546(2) 0.11154(19) 0.8139(2) 0.0431(5) Uani 1 1 d . . . . .
H22 H 0.770086 0.042608 0.838862 0.052 Uiso 1 1 calc R U . . .
C23 C 0.6401(2) 0.16379(16) 0.8365(2) 0.0347(4) Uani 1 1 d . . . . .
H23 H 0.579141 0.130667 0.878529 0.042 Uiso 1 1 calc R U . . .
C24 C 0.46901(19) 0.68990(14) 0.73884(19) 0.0274(4) Uani 1 1 d . . . . .
C25 C 0.4330(2) 0.63383(18) 0.5994(2) 0.0376(4) Uani 1 1 d . . . . .
H25A H 0.410311 0.563418 0.611424 0.056 Uiso 1 1 calc R U . . .
H25B H 0.519423 0.637222 0.569769 0.056 Uiso 1 1 calc R U . . .
H25C H 0.346391 0.665126 0.528236 0.056 Uiso 1 1 calc R U . . .
C26 C 0.5745(2) 0.62642(15) 0.8595(2) 0.0339(4) Uani 1 1 d . . . . .
H26A H 0.612284 0.667546 0.944262 0.051 Uiso 1 1 calc R U . . .
H26B H 0.658560 0.602616 0.834776 0.051 Uiso 1 1 calc R U . . .
H26C H 0.519702 0.568690 0.876266 0.051 Uiso 1 1 calc R U . . .
C27 C 0.5494(2) 0.78815(15) 0.7301(2) 0.0382(5) Uani 1 1 d . . . . .
H27A H 0.484982 0.828457 0.651514 0.057 Uiso 1 1 calc R U . . .
H27B H 0.642926 0.772640 0.715927 0.057 Uiso 1 1 calc R U . . .
H27C H 0.571431 0.826022 0.817132 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.223(2) . ?
O2 C9 1.197(2) . ?
O3 C12 1.198(2) . ?
O4 C15 1.201(2) . ?
O5 C15 1.326(2) . ?
O5 C16 1.458(3) . ?
N1 C5 1.394(2) . ?
N1 C8 1.284(2) . ?
N2 N3 1.388(2) . ?
N2 C7 1.416(2) . ?
N2 C8 1.408(2) . ?
N3 C9 1.409(2) . ?
N3 C12 1.410(2) . ?
N4 C13 1.459(2) . ?
N4 C14 1.463(3) . ?
N4 H4 0.87(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(3) . ?
C1 C6 1.398(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 H4A 0.9500 . ?
C4 C5 1.403(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.447(3) . ?
C8 C24 1.537(2) . ?
C9 C10 1.516(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.547(2) . ?
C10 C14 1.534(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.514(2) . ?
C11 C13 1.559(2) . ?
C13 C15 1.547(2) . ?
C13 C17 1.544(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.507(2) . ?
C18 C19 1.385(3) . ?
C18 C23 1.393(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.538(3) . ?
C24 C26 1.539(3) . ?
C24 C27 1.537(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O5 C16 115.55(18) . . ?
C8 N1 C5 120.07(16) . . ?
N3 N2 C7 112.56(14) . . ?
N3 N2 C8 122.69(14) . . ?
C8 N2 C7 124.37(15) . . ?
N2 N3 C9 118.27(14) . . ?
N2 N3 C12 119.93(14) . . ?
C9 N3 C12 112.68(15) . . ?
C13 N4 C14 106.47(15) . . ?
C13 N4 H4 110(2) . . ?
C14 N4 H4 111(2) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.91(19) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.11(18) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.69(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4A 120.1 . . ?
C3 C4 C5 119.75(19) . . ?
C5 C4 H4A 120.1 . . ?
N1 C5 C4 118.06(17) . . ?
N1 C5 C6 122.76(17) . . ?
C6 C5 C4 119.16(17) . . ?
C1 C6 C5 120.36(17) . . ?
C1 C6 C7 120.86(17) . . ?
C5 C6 C7 118.77(16) . . ?
O1 C7 N2 119.82(17) . . ?
O1 C7 C6 126.56(17) . . ?
N2 C7 C6 113.62(15) . . ?
N1 C8 N2 120.24(15) . . ?
N1 C8 C24 118.83(16) . . ?
N2 C8 C24 120.80(15) . . ?
O2 C9 N3 123.59(17) . . ?
O2 C9 C10 128.77(17) . . ?
N3 C9 C10 107.64(15) . . ?
C9 C10 H10 111.2 . . ?
C9 C10 C11 104.93(14) . . ?
C9 C10 C14 112.88(16) . . ?
C11 C10 H10 111.2 . . ?
C14 C10 H10 111.2 . . ?
C14 C10 C11 105.17(14) . . ?
C10 C11 H11 111.0 . . ?
C10 C11 C13 104.48(13) . . ?
C12 C11 C10 105.55(14) . . ?
C12 C11 H11 111.0 . . ?
C12 C11 C13 113.50(14) . . ?
C13 C11 H11 111.0 . . ?
O3 C12 N3 124.37(17) . . ?
O3 C12 C11 128.72(17) . . ?
N3 C12 C11 106.91(14) . . ?
N4 C13 C11 101.99(14) . . ?
N4 C13 C15 115.55(15) . . ?
N4 C13 C17 111.00(14) . . ?
C15 C13 C11 107.54(14) . . ?
C17 C13 C11 114.19(14) . . ?
C17 C13 C15 106.73(14) . . ?
N4 C14 C10 101.61(14) . . ?
N4 C14 H14A 111.4 . . ?
N4 C14 H14B 111.4 . . ?
C10 C14 H14A 111.4 . . ?
C10 C14 H14B 111.4 . . ?
H14A C14 H14B 109.3 . . ?
O4 C15 O5 124.87(18) . . ?
O4 C15 C13 122.80(17) . . ?
O5 C15 C13 112.24(15) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 108.8 . . ?
C13 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C13 113.78(14) . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C19 C18 C17 120.70(18) . . ?
C19 C18 C23 118.70(18) . . ?
C23 C18 C17 120.60(17) . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(2) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.7(2) . . ?
C22 C23 H23 119.7 . . ?
C8 C24 C25 113.79(15) . . ?
C8 C24 C26 108.40(14) . . ?
C25 C24 C26 110.13(16) . . ?
C27 C24 C8 107.97(15) . . ?
C27 C24 C25 107.97(15) . . ?
C27 C24 C26 108.44(15) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C9 C10 C11 -175.15(18) . . . . ?
O2 C9 C10 C14 70.9(2) . . . . ?
N1 C5 C6 C1 176.99(17) . . . . ?
N1 C5 C6 C7 -2.5(2) . . . . ?
N1 C8 C24 C25 -129.76(18) . . . . ?
N1 C8 C24 C26 107.36(19) . . . . ?
N1 C8 C24 C27 -9.9(2) . . . . ?
N2 N3 C9 O2 19.6(3) . . . . ?
N2 N3 C9 C10 -160.57(14) . . . . ?
N2 N3 C12 O3 -17.7(3) . . . . ?
N2 N3 C12 C11 162.65(14) . . . . ?
N2 C8 C24 C25 54.2(2) . . . . ?
N2 C8 C24 C26 -68.7(2) . . . . ?
N2 C8 C24 C27 174.04(15) . . . . ?
N3 N2 C7 O1 3.0(2) . . . . ?
N3 N2 C7 C6 -176.64(14) . . . . ?
N3 N2 C8 N1 172.65(16) . . . . ?
N3 N2 C8 C24 -11.4(2) . . . . ?
N3 C9 C10 C11 5.07(18) . . . . ?
N3 C9 C10 C14 -108.91(17) . . . . ?
N4 C13 C15 O4 -162.51(18) . . . . ?
N4 C13 C15 O5 20.7(2) . . . . ?
N4 C13 C17 C18 -64.14(19) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C7 O1 5.4(3) . . . . ?
C1 C6 C7 N2 -175.01(15) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 179.76(17) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 N1 -176.78(17) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C4 C5 C6 C1 -1.4(2) . . . . ?
C4 C5 C6 C7 179.08(16) . . . . ?
C5 N1 C8 N2 2.1(2) . . . . ?
C5 N1 C8 C24 -173.93(15) . . . . ?
C5 C6 C7 O1 -175.14(17) . . . . ?
C5 C6 C7 N2 4.5(2) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 N2 N3 C9 72.43(19) . . . . ?
C7 N2 N3 C12 -72.13(19) . . . . ?
C7 N2 C8 N1 0.3(2) . . . . ?
C7 N2 C8 C24 176.31(15) . . . . ?
C8 N1 C5 C4 177.38(16) . . . . ?
C8 N1 C5 C6 -1.0(3) . . . . ?
C8 N2 N3 C9 -100.71(18) . . . . ?
C8 N2 N3 C12 114.73(18) . . . . ?
C8 N2 C7 O1 176.02(16) . . . . ?
C8 N2 C7 C6 -3.6(2) . . . . ?
C9 N3 C12 O3 -164.14(16) . . . . ?
C9 N3 C12 C11 16.25(19) . . . . ?
C9 C10 C11 C12 4.16(18) . . . . ?
C9 C10 C11 C13 -115.79(15) . . . . ?
C9 C10 C14 N4 85.48(18) . . . . ?
C10 C11 C12 O3 168.46(17) . . . . ?
C10 C11 C12 N3 -11.95(17) . . . . ?
C10 C11 C13 N4 22.74(17) . . . . ?
C10 C11 C13 C15 -99.23(15) . . . . ?
C10 C11 C13 C17 142.55(14) . . . . ?
C11 C10 C14 N4 -28.35(19) . . . . ?
C11 C13 C15 O4 -49.4(2) . . . . ?
C11 C13 C15 O5 133.82(15) . . . . ?
C11 C13 C17 C18 -178.75(15) . . . . ?
C12 N3 C9 O2 166.64(17) . . . . ?
C12 N3 C9 C10 -13.56(19) . . . . ?
C12 C11 C13 N4 -91.73(16) . . . . ?
C12 C11 C13 C15 146.30(14) . . . . ?
C12 C11 C13 C17 28.1(2) . . . . ?
C13 N4 C14 C10 45.28(19) . . . . ?
C13 C11 C12 O3 -77.7(2) . . . . ?
C13 C11 C12 N3 101.88(16) . . . . ?
C13 C17 C18 C19 94.5(2) . . . . ?
C13 C17 C18 C23 -86.6(2) . . . . ?
C14 N4 C13 C11 -42.93(18) . . . . ?
C14 N4 C13 C15 73.37(18) . . . . ?
C14 N4 C13 C17 -164.95(15) . . . . ?
C14 C10 C11 C12 123.44(15) . . . . ?
C14 C10 C11 C13 3.49(18) . . . . ?
C15 C13 C17 C18 62.57(18) . . . . ?
C16 O5 C15 O4 -5.1(3) . . . . ?
C16 O5 C15 C13 171.60(18) . . . . ?
C17 C13 C15 O4 73.5(2) . . . . ?
C17 C13 C15 O5 -103.24(16) . . . . ?
C17 C18 C19 C20 179.55(18) . . . . ?
C17 C18 C23 C22 179.97(18) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C18 C23 C22 -1.1(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C21 C22 C23 C18 1.3(3) . . . . ?
C23 C18 C19 C20 0.6(3) . . . . ?

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

data_cu_221109_wt_fp_bn_0m
_database_code_depnum_ccdc_archive 'CCDC 2261239'
loop_
_audit_author_name
_audit_author_address
'Wen-Tao Wang'
;Zhejiang University
China
;
_audit_update_record             
;
2023-05-07 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2022-11-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 N4 O5'
_chemical_formula_sum            'C30 H24 N4 O5'
_chemical_formula_weight         520.53
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6482(5)
_cell_length_b                   9.5877(7)
_cell_length_c                   10.0552(7)
_cell_angle_alpha                115.079(2)
_cell_angle_beta                 99.469(2)
_cell_angle_gamma                97.668(2)
_cell_volume                     641.46(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9778
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      5.23
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.709
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.7704.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21343
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.391
_diffrn_reflns_theta_min         5.230
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                4524
_reflns_number_total             4563
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2154 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4563
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.0496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0782
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C20(H20), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1721(2) 0.45859(17) 0.37977(18) 0.0429(4) Uani 1 1 d . . . . .
O2 O 0.56764(19) 0.36471(15) 0.25265(15) 0.0335(3) Uani 1 1 d . . . . .
O3 O 0.4382(2) 0.54175(17) 0.71438(16) 0.0386(3) Uani 1 1 d . . . . .
O4 O 0.7264(3) 0.6335(2) 0.17841(19) 0.0657(6) Uani 1 1 d . . . . .
O5 O 0.4798(3) 0.6712(2) 0.2704(2) 0.0619(5) Uani 1 1 d . . . . .
N1 N 0.2368(2) 0.01545(19) 0.29804(18) 0.0334(4) Uani 1 1 d . . . . .
N2 N 0.3414(2) 0.29070(18) 0.40946(18) 0.0284(3) Uani 1 1 d . . . . .
N3 N 0.4913(2) 0.41690(17) 0.47652(17) 0.0266(3) Uani 1 1 d . . . . .
N4 N 0.6680(2) 0.84722(19) 0.5475(2) 0.0343(4) Uani 1 1 d . . . . .
C1 C -0.1233(3) 0.1925(3) 0.1731(2) 0.0398(5) Uani 1 1 d . . . . .
H1 H -0.142630 0.292558 0.185218 0.048 Uiso 1 1 calc R U . . .
C2 C -0.2538(3) 0.0564(3) 0.0776(3) 0.0463(6) Uani 1 1 d . . . . .
H2 H -0.364379 0.062634 0.023702 0.056 Uiso 1 1 calc R U . . .
C3 C -0.2250(3) -0.0903(3) 0.0594(3) 0.0465(5) Uani 1 1 d . . . . .
H3 H -0.317213 -0.182996 -0.005480 0.056 Uiso 1 1 calc R U . . .
C4 C -0.0643(3) -0.1029(3) 0.1344(2) 0.0416(5) Uani 1 1 d . . . . .
H4 H -0.045901 -0.203807 0.120282 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0714(3) 0.0332(2) 0.2312(2) 0.0326(4) Uani 1 1 d . . . . .
C6 C 0.0392(3) 0.1809(2) 0.2523(2) 0.0315(4) Uani 1 1 d . . . . .
C7 C 0.1803(3) 0.3232(2) 0.3497(2) 0.0312(4) Uani 1 1 d . . . . .
C8 C 0.3666(3) 0.1381(2) 0.3774(2) 0.0291(4) Uani 1 1 d . . . . .
C9 C 0.5537(3) 0.1184(2) 0.4297(2) 0.0351(4) Uani 1 1 d . . . . .
H9A H 0.630065 0.136647 0.365589 0.042 Uiso 1 1 calc R U . . .
H9B H 0.542686 0.006808 0.409745 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6551(3) 0.2220(2) 0.5935(2) 0.0356(4) Uani 1 1 d . . . . .
C11 C 0.5804(3) 0.2239(3) 0.7101(3) 0.0435(5) Uani 1 1 d . . . . .
H11 H 0.462652 0.160563 0.687825 0.052 Uiso 1 1 calc R U . . .
C12 C 0.6771(4) 0.3186(3) 0.8608(3) 0.0574(7) Uani 1 1 d . . . . .
H12 H 0.624404 0.320987 0.940768 0.069 Uiso 1 1 calc R U . . .
C13 C 0.8506(4) 0.4094(3) 0.8934(3) 0.0635(8) Uani 1 1 d . . . . .
H13 H 0.916730 0.473518 0.995745 0.076 Uiso 1 1 calc R U . . .
C14 C 0.9261(4) 0.4066(3) 0.7789(4) 0.0595(8) Uani 1 1 d . . . . .
H14 H 1.044868 0.468462 0.801692 0.071 Uiso 1 1 calc R U . . .
C15 C 0.8295(3) 0.3132(3) 0.6285(3) 0.0466(5) Uani 1 1 d . . . . .
H15 H 0.883021 0.311773 0.549275 0.056 Uiso 1 1 calc R U . . .
C16 C 0.5248(3) 0.5384(2) 0.6247(2) 0.0287(4) Uani 1 1 d . . . . .
C17 C 0.6871(2) 0.6602(2) 0.6419(2) 0.0283(4) Uani 1 1 d . . . . .
H17 H 0.789454 0.682999 0.729469 0.034 Uiso 1 1 calc R U . . .
C18 C 0.7433(2) 0.5942(2) 0.4913(2) 0.0265(4) Uani 1 1 d . . . . .
H18 H 0.864046 0.566028 0.504855 0.032 Uiso 1 1 calc R U . . .
C19 C 0.5954(2) 0.4480(2) 0.3875(2) 0.0265(4) Uani 1 1 d . . . . .
C20 C 0.6356(3) 0.8105(2) 0.6488(2) 0.0319(4) Uani 1 1 d . . . . .
H20 H 0.581945 0.873412 0.725407 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7562(3) 0.7329(2) 0.4475(2) 0.0305(4) Uani 1 1 d . . . . .
C22 C 0.6553(3) 0.6743(2) 0.2816(3) 0.0413(5) Uani 1 1 d . . . . .
C23 C 0.3646(6) 0.6069(5) 0.1189(5) 0.0939(14) Uani 1 1 d . . . . .
H23A H 0.390785 0.505905 0.054361 0.141 Uiso 1 1 calc R U . . .
H23B H 0.388544 0.681262 0.077231 0.141 Uiso 1 1 calc R U . . .
H23C H 0.236599 0.590046 0.122414 0.141 Uiso 1 1 calc R U . . .
C24 C 0.9559(3) 0.8133(2) 0.4715(2) 0.0362(4) Uani 1 1 d . . . . .
H24A H 1.015785 0.734147 0.406875 0.043 Uiso 1 1 calc R U . . .
H24B H 0.957263 0.897335 0.438783 0.043 Uiso 1 1 calc R U . . .
C25 C 1.0637(2) 0.8853(2) 0.6351(2) 0.0322(4) Uani 1 1 d . . . . .
C26 C 1.1635(3) 0.8008(2) 0.6876(2) 0.0363(4) Uani 1 1 d . . . . .
H26 H 1.168959 0.697074 0.619503 0.044 Uiso 1 1 calc R U . . .
C27 C 1.2561(3) 0.8667(3) 0.8397(3) 0.0418(5) Uani 1 1 d . . . . .
H27 H 1.322435 0.807021 0.875146 0.050 Uiso 1 1 calc R U . . .
C28 C 1.2516(3) 1.0186(3) 0.9389(2) 0.0418(5) Uani 1 1 d . . . . .
H28 H 1.316115 1.063812 1.042166 0.050 Uiso 1 1 calc R U . . .
C29 C 1.1538(3) 1.1039(3) 0.8881(3) 0.0465(5) Uani 1 1 d . . . . .
H29 H 1.150497 1.208285 0.956313 0.056 Uiso 1 1 calc R U . . .
C30 C 1.0594(3) 1.0378(2) 0.7367(3) 0.0413(5) Uani 1 1 d . . . . .
H30 H 0.991286 1.097227 0.702390 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.215(3) . ?
O2 C19 1.210(2) . ?
O3 C16 1.197(2) . ?
O4 C22 1.193(3) . ?
O5 C22 1.324(3) . ?
O5 C23 1.447(3) . ?
N1 C5 1.399(3) . ?
N1 C8 1.280(3) . ?
N2 N3 1.384(2) . ?
N2 C7 1.412(2) . ?
N2 C8 1.406(2) . ?
N3 C16 1.402(2) . ?
N3 C19 1.386(2) . ?
N4 C20 1.259(3) . ?
N4 C21 1.468(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(3) . ?
C1 C6 1.406(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.454(3) . ?
C8 C9 1.506(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.513(3) . ?
C10 C11 1.381(3) . ?
C10 C15 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.362(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.518(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.533(2) . ?
C17 C20 1.521(3) . ?
C18 H18 1.0000 . ?
C18 C19 1.510(2) . ?
C18 C21 1.565(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.536(3) . ?
C21 C24 1.547(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.517(3) . ?
C25 C26 1.383(3) . ?
C25 C30 1.393(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.395(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.382(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.372(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.392(3) . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O5 C23 116.6(3) . . ?
C8 N1 C5 118.82(16) . . ?
N3 N2 C7 114.80(14) . . ?
N3 N2 C8 119.25(14) . . ?
C8 N2 C7 124.50(15) . . ?
N2 N3 C16 123.89(15) . . ?
N2 N3 C19 119.68(14) . . ?
C19 N3 C16 114.93(15) . . ?
C20 N4 C21 110.25(16) . . ?
C2 C1 H1 120.5 . . ?
C2 C1 C6 118.9(2) . . ?
C6 C1 H1 120.5 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 118.35(19) . . ?
N1 C5 C6 122.72(17) . . ?
C4 C5 C6 118.87(19) . . ?
C1 C6 C7 119.40(19) . . ?
C5 C6 C1 120.89(18) . . ?
C5 C6 C7 119.59(17) . . ?
O1 C7 N2 120.20(18) . . ?
O1 C7 C6 127.14(19) . . ?
N2 C7 C6 112.65(16) . . ?
N1 C8 N2 121.49(17) . . ?
N1 C8 C9 119.41(17) . . ?
N2 C8 C9 118.99(15) . . ?
C8 C9 H9A 107.8 . . ?
C8 C9 H9B 107.8 . . ?
C8 C9 C10 118.13(17) . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 H9A 107.8 . . ?
C10 C9 H9B 107.8 . . ?
C11 C10 C9 121.10(19) . . ?
C11 C10 C15 118.9(2) . . ?
C15 C10 C9 119.9(2) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.5(3) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O3 C16 N3 125.38(18) . . ?
O3 C16 C17 129.09(17) . . ?
N3 C16 C17 105.52(15) . . ?
C16 C17 H17 111.9 . . ?
C16 C17 C18 106.53(14) . . ?
C16 C17 C20 112.55(15) . . ?
C18 C17 H17 111.9 . . ?
C20 C17 H17 111.9 . . ?
C20 C17 C18 101.43(14) . . ?
C17 C18 H18 110.6 . . ?
C17 C18 C21 104.23(14) . . ?
C19 C18 C17 104.49(14) . . ?
C19 C18 H18 110.6 . . ?
C19 C18 C21 115.95(14) . . ?
C21 C18 H18 110.6 . . ?
O2 C19 N3 123.04(16) . . ?
O2 C19 C18 129.70(17) . . ?
N3 C19 C18 107.22(14) . . ?
N4 C20 C17 116.46(17) . . ?
N4 C20 H20 121.8 . . ?
C17 C20 H20 121.8 . . ?
N4 C21 C18 105.85(15) . . ?
N4 C21 C22 109.48(17) . . ?
N4 C21 C24 109.66(15) . . ?
C22 C21 C18 111.03(15) . . ?
C22 C21 C24 108.84(16) . . ?
C24 C21 C18 111.93(16) . . ?
O4 C22 O5 125.6(2) . . ?
O4 C22 C21 124.0(2) . . ?
O5 C22 C21 110.4(2) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.0 . . ?
C21 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 C21 112.72(15) . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C26 C25 C24 121.29(18) . . ?
C26 C25 C30 118.68(19) . . ?
C30 C25 C24 120.01(19) . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.5(2) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.1(2) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 119.9(2) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.0(2) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 H30 119.7 . . ?
C29 C30 C25 120.7(2) . . ?
C29 C30 H30 119.7 . . ?

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
O3 C16 C17 C18 179.98(18) . . . . ?
O3 C16 C17 C20 -69.7(2) . . . . ?
N1 C5 C6 C1 174.60(18) . . . . ?
N1 C5 C6 C7 -1.4(3) . . . . ?
N1 C8 C9 C10 -133.48(18) . . . . ?
N2 N3 C16 O3 6.4(3) . . . . ?
N2 N3 C16 C17 -172.54(15) . . . . ?
N2 N3 C19 O2 -3.9(2) . . . . ?
N2 N3 C19 C18 178.16(14) . . . . ?
N2 C8 C9 C10 50.2(2) . . . . ?
N3 N2 C7 O1 -11.7(3) . . . . ?
N3 N2 C7 C6 167.22(15) . . . . ?
N3 N2 C8 N1 -170.69(16) . . . . ?
N3 N2 C8 C9 5.5(2) . . . . ?
N3 C16 C17 C18 -1.11(18) . . . . ?
N3 C16 C17 C20 109.19(17) . . . . ?
N4 C21 C22 O4 149.8(2) . . . . ?
N4 C21 C22 O5 -32.2(2) . . . . ?
N4 C21 C24 C25 56.3(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C6 C7 O1 4.6(3) . . . . ?
C1 C6 C7 N2 -174.17(17) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
C2 C1 C6 C7 178.09(18) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 N1 -176.08(19) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C5 C6 C1 -2.6(3) . . . . ?
C4 C5 C6 C7 -178.56(17) . . . . ?
C5 N1 C8 N2 5.6(3) . . . . ?
C5 N1 C8 C9 -170.56(17) . . . . ?
C5 C6 C7 O1 -179.3(2) . . . . ?
C5 C6 C7 N2 1.9(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 N2 N3 C16 81.4(2) . . . . ?
C7 N2 N3 C19 -83.93(19) . . . . ?
C7 N2 C8 N1 -5.2(3) . . . . ?
C7 N2 C8 C9 170.99(17) . . . . ?
C8 N1 C5 C4 174.69(17) . . . . ?
C8 N1 C5 C6 -2.5(3) . . . . ?
C8 N2 N3 C16 -111.75(19) . . . . ?
C8 N2 N3 C19 82.9(2) . . . . ?
C8 N2 C7 O1 -177.75(18) . . . . ?
C8 N2 C7 C6 1.1(2) . . . . ?
C8 C9 C10 C11 56.6(2) . . . . ?
C8 C9 C10 C15 -125.7(2) . . . . ?
C9 C10 C11 C12 179.06(19) . . . . ?
C9 C10 C15 C14 -178.60(19) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
C16 N3 C19 O2 -170.47(17) . . . . ?
C16 N3 C19 C18 11.57(19) . . . . ?
C16 C17 C18 C19 7.38(17) . . . . ?
C16 C17 C18 C21 129.51(15) . . . . ?
C16 C17 C20 N4 -120.27(19) . . . . ?
C17 C18 C19 O2 171.05(18) . . . . ?
C17 C18 C19 N3 -11.16(17) . . . . ?
C17 C18 C21 N4 -13.27(18) . . . . ?
C17 C18 C21 C22 -131.99(17) . . . . ?
C17 C18 C21 C24 106.15(17) . . . . ?
C18 C17 C20 N4 -6.8(2) . . . . ?
C18 C21 C22 O4 -93.7(2) . . . . ?
C18 C21 C22 O5 84.3(2) . . . . ?
C18 C21 C24 C25 -60.8(2) . . . . ?
C19 N3 C16 O3 172.38(17) . . . . ?
C19 N3 C16 C17 -6.58(19) . . . . ?
C19 C18 C21 N4 100.97(17) . . . . ?
C19 C18 C21 C22 -17.8(2) . . . . ?
C19 C18 C21 C24 -139.61(16) . . . . ?
C20 N4 C21 C18 9.7(2) . . . . ?
C20 N4 C21 C22 129.43(18) . . . . ?
C20 N4 C21 C24 -111.22(18) . . . . ?
C20 C17 C18 C19 -110.53(15) . . . . ?
C20 C17 C18 C21 11.60(17) . . . . ?
C21 N4 C20 C17 -1.9(2) . . . . ?
C21 C18 C19 O2 57.0(3) . . . . ?
C21 C18 C19 N3 -125.25(16) . . . . ?
C21 C24 C25 C26 92.5(2) . . . . ?
C21 C24 C25 C30 -85.8(2) . . . . ?
C22 C21 C24 C25 176.07(17) . . . . ?
C23 O5 C22 O4 2.5(4) . . . . ?
C23 O5 C22 C21 -175.5(2) . . . . ?
C24 C21 C22 O4 30.0(3) . . . . ?
C24 C21 C22 O5 -152.04(17) . . . . ?
C24 C25 C26 C27 -177.58(18) . . . . ?
C24 C25 C30 C29 178.38(19) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C26 C25 C30 C29 0.1(3) . . . . ?
C26 C27 C28 C29 0.9(3) . . . . ?
C27 C28 C29 C30 -0.1(3) . . . . ?
C28 C29 C30 C25 -0.4(3) . . . . ?
C30 C25 C26 C27 0.7(3) . . . . ?

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

data_230301_wf_fp_ind_0m
_database_code_depnum_ccdc_archive 'CCDC 2261241'
loop_
_audit_author_name
_audit_author_address
'Wen-Tao Wang'
;Zhejiang University
China
;
_audit_update_record             
;
2023-05-07 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-03-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H23 N3 O6'
_chemical_formula_sum            'C26 H23 N3 O6'
_chemical_formula_weight         473.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.7753(6)
_cell_length_b                   7.5349(4)
_cell_length_c                   13.0392(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.653(2)
_cell_angle_gamma                90
_cell_volume                     1151.29(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.667
_cell_measurement_theta_min      2.963
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0926 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.9233.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22355
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.966
_diffrn_reflns_theta_min         2.963
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                4441
_reflns_number_total             4618
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4618
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.1099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19345(13) 0.9707(2) 0.43091(13) 0.0368(4) Uani 1 1 d . . . . .
O2 O 0.36333(12) 0.92605(19) 0.52075(11) 0.0290(3) Uani 1 1 d . . . . .
O3 O 0.38064(12) 0.6900(2) 0.33811(11) 0.0324(3) Uani 1 1 d . . . . .
O4 O 0.06069(14) 0.3576(3) 0.26104(12) 0.0414(4) Uani 1 1 d . . . . .
O5 O 0.36085(18) 0.2524(3) 0.23938(14) 0.0542(5) Uani 1 1 d . . . . .
O6 O 0.34942(13) 0.1649(2) 0.07407(12) 0.0342(4) Uani 1 1 d . . . . .
N1 N 0.09849(15) 0.6930(3) 0.52256(14) 0.0298(4) Uani 1 1 d . . . . .
N2 N 0.21961(14) 0.5361(2) 0.28028(12) 0.0246(4) Uani 1 1 d . . . . .
N3 N 0.23000(14) 0.5602(2) 0.17687(12) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.1523(2) 0.4330(3) 0.71368(17) 0.0363(5) Uani 1 1 d . . . . .
H1 H 0.087980 0.509714 0.706931 0.044 Uiso 1 1 calc R U . . .
C2 C 0.1417(2) 0.2629(4) 0.75140(19) 0.0423(6) Uani 1 1 d . . . . .
H2 H 0.069700 0.222777 0.769149 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2348(3) 0.1509(3) 0.7635(2) 0.0448(6) Uani 1 1 d . . . . .
H3 H 0.227015 0.034754 0.790286 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3388(2) 0.2074(4) 0.73666(19) 0.0449(6) Uani 1 1 d . . . . .
H4 H 0.402994 0.130565 0.744796 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3497(2) 0.3772(4) 0.69768(18) 0.0380(5) Uani 1 1 d . . . . .
H5 H 0.421697 0.415531 0.678938 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2569(2) 0.4925(3) 0.68555(15) 0.0307(5) Uani 1 1 d . . . . .
C7 C 0.2719(2) 0.6766(3) 0.64379(16) 0.0346(5) Uani 1 1 d . . . . .
H7A H 0.354343 0.705585 0.650312 0.042 Uiso 1 1 calc R U . . .
H7B H 0.233774 0.762397 0.686549 0.042 Uiso 1 1 calc R U . . .
C8 C 0.22350(16) 0.7003(3) 0.52947(15) 0.0253(4) Uani 1 1 d . . . . .
C9 C 0.06260(17) 0.5542(3) 0.47452(16) 0.0289(4) Uani 1 1 d . . . . .
H9 H -0.016171 0.524518 0.465702 0.035 Uiso 1 1 calc R U . . .
C10 C 0.15177(16) 0.4389(3) 0.43222(14) 0.0229(4) Uani 1 1 d . . . . .
H10 H 0.156151 0.318220 0.464294 0.028 Uiso 1 1 calc R U . . .
C11 C 0.26148(16) 0.5468(3) 0.45865(14) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.321407 0.471670 0.497107 0.026 Uiso 1 1 calc R U . . .
C12 C 0.29927(16) 0.6035(3) 0.35547(15) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.13376(16) 0.4309(3) 0.31567(15) 0.0264(4) Uani 1 1 d . . . . .
C14 C 0.25644(16) 0.8824(3) 0.48823(15) 0.0248(4) Uani 1 1 d . . . . .
C15 C 0.40449(19) 1.0861(3) 0.47489(19) 0.0349(5) Uani 1 1 d . . . . .
H15A H 0.407130 1.067631 0.400758 0.052 Uiso 1 1 calc R U . . .
H15B H 0.481218 1.113848 0.506932 0.052 Uiso 1 1 calc R U . . .
H15C H 0.352934 1.184806 0.485972 0.052 Uiso 1 1 calc R U . . .
C16 C 0.17806(15) 0.6992(3) 0.12154(15) 0.0240(4) Uani 1 1 d . . . . .
C17 C 0.13556(17) 0.8580(3) 0.15660(17) 0.0302(4) Uani 1 1 d . . . . .
H17 H 0.136686 0.883547 0.228036 0.036 Uiso 1 1 calc R U . . .
C18 C 0.09172(17) 0.9763(3) 0.08233(18) 0.0347(5) Uani 1 1 d . . . . .
H18 H 0.062699 1.087040 0.102783 0.042 Uiso 1 1 calc R U . . .
C19 C 0.08918(17) 0.9359(3) -0.02305(18) 0.0352(5) Uani 1 1 d . . . . .
H19 H 0.056164 1.018551 -0.072339 0.042 Uiso 1 1 calc R U . . .
C20 C 0.13327(17) 0.7800(3) -0.05655(17) 0.0312(5) Uani 1 1 d . . . . .
H20 H 0.132273 0.755857 -0.128147 0.037 Uiso 1 1 calc R U . . .
C21 C 0.17988(16) 0.6565(3) 0.01672(15) 0.0250(4) Uani 1 1 d . . . . .
C22 C 0.23302(17) 0.4863(3) 0.01144(16) 0.0277(4) Uani 1 1 d . . . . .
H22 H 0.245854 0.424190 -0.049760 0.033 Uiso 1 1 calc R U . . .
C23 C 0.26195(16) 0.4291(3) 0.10972(16) 0.0264(4) Uani 1 1 d . . . . .
C24 C 0.32748(19) 0.2736(3) 0.14964(18) 0.0326(5) Uani 1 1 d . . . . .
C25 C 0.4228(2) 0.0147(3) 0.1048(2) 0.0460(6) Uani 1 1 d . . . . .
H25A H 0.386011 -0.062394 0.153329 0.055 Uiso 1 1 calc R U . . .
H25B H 0.496608 0.056765 0.139234 0.055 Uiso 1 1 calc R U . . .
C26 C 0.4415(2) -0.0857(4) 0.0092(3) 0.0567(8) Uani 1 1 d . . . . .
H26A H 0.478509 -0.008331 -0.037920 0.085 Uiso 1 1 calc R U . . .
H26B H 0.367900 -0.126111 -0.024303 0.085 Uiso 1 1 calc R U . . .
H26C H 0.490376 -0.188610 0.027141 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.201(3) . ?
O2 C14 1.329(2) . ?
O2 C15 1.450(3) . ?
O3 C12 1.199(2) . ?
O4 C13 1.197(3) . ?
O5 C24 1.208(3) . ?
O6 C24 1.326(3) . ?
O6 C25 1.456(3) . ?
N1 C8 1.467(3) . ?
N1 C9 1.270(3) . ?
N2 N3 1.378(2) . ?
N2 C12 1.385(3) . ?
N2 C13 1.399(3) . ?
N3 C16 1.380(3) . ?
N3 C23 1.396(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(4) . ?
C6 C7 1.507(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.553(3) . ?
C8 C11 1.572(3) . ?
C8 C14 1.538(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.508(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.536(3) . ?
C10 C13 1.515(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.519(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.391(3) . ?
C16 C21 1.406(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.405(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.373(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.406(3) . ?
C21 C22 1.432(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.363(3) . ?
C23 C24 1.469(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.492(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O2 C15 114.74(16) . . ?
C24 O6 C25 115.44(19) . . ?
C9 N1 C8 110.15(18) . . ?
N3 N2 C12 121.70(17) . . ?
N3 N2 C13 122.30(16) . . ?
C12 N2 C13 115.81(16) . . ?
N2 N3 C16 122.27(17) . . ?
N2 N3 C23 125.17(18) . . ?
C16 N3 C23 110.01(16) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.3(2) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.3(2) . . ?
C1 C6 C7 122.0(2) . . ?
C5 C6 C7 119.7(2) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.04(17) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N1 C8 C7 109.03(17) . . ?
N1 C8 C11 106.14(16) . . ?
N1 C8 C14 107.35(16) . . ?
C7 C8 C11 112.36(17) . . ?
C14 C8 C7 110.91(16) . . ?
C14 C8 C11 110.80(15) . . ?
N1 C9 H9 121.8 . . ?
N1 C9 C10 116.41(18) . . ?
C10 C9 H9 121.8 . . ?
C9 C10 H10 112.3 . . ?
C9 C10 C11 102.33(16) . . ?
C9 C10 C13 110.86(16) . . ?
C11 C10 H10 112.3 . . ?
C13 C10 H10 112.3 . . ?
C13 C10 C11 106.12(15) . . ?
C8 C11 H11 110.4 . . ?
C10 C11 C8 103.86(15) . . ?
C10 C11 H11 110.4 . . ?
C12 C11 C8 116.00(16) . . ?
C12 C11 C10 105.26(15) . . ?
C12 C11 H11 110.4 . . ?
O3 C12 N2 124.33(18) . . ?
O3 C12 C11 129.00(18) . . ?
N2 C12 C11 106.67(16) . . ?
O4 C13 N2 124.47(19) . . ?
O4 C13 C10 129.57(19) . . ?
N2 C13 C10 105.91(16) . . ?
O1 C14 O2 124.69(19) . . ?
O1 C14 C8 123.39(18) . . ?
O2 C14 C8 111.88(16) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 129.50(19) . . ?
N3 C16 C21 106.62(18) . . ?
C17 C16 C21 123.81(19) . . ?
C16 C17 H17 121.7 . . ?
C18 C17 C16 116.6(2) . . ?
C18 C17 H17 121.7 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.6(2) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.0(2) . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C22 107.47(18) . . ?
C20 C21 C16 117.8(2) . . ?
C20 C21 C22 134.7(2) . . ?
C21 C22 H22 126.0 . . ?
C23 C22 C21 107.95(19) . . ?
C23 C22 H22 126.0 . . ?
N3 C23 C24 120.44(18) . . ?
C22 C23 N3 107.93(18) . . ?
C22 C23 C24 131.2(2) . . ?
O5 C24 O6 124.7(2) . . ?
O5 C24 C23 123.9(2) . . ?
O6 C24 C23 111.29(18) . . ?
O6 C25 H25A 110.3 . . ?
O6 C25 H25B 110.3 . . ?
O6 C25 C26 107.3(2) . . ?
H25A C25 H25B 108.5 . . ?
C26 C25 H25A 110.3 . . ?
C26 C25 H25B 110.3 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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 C8 C11 C10 -10.61(19) . . . . ?
N1 C8 C11 C12 104.35(18) . . . . ?
N1 C8 C14 O1 -22.5(3) . . . . ?
N1 C8 C14 O2 159.68(16) . . . . ?
N1 C9 C10 C11 -3.9(2) . . . . ?
N1 C9 C10 C13 -116.7(2) . . . . ?
N2 N3 C16 C17 18.8(3) . . . . ?
N2 N3 C16 C21 -164.20(17) . . . . ?
N2 N3 C23 C22 163.63(18) . . . . ?
N2 N3 C23 C24 -22.9(3) . . . . ?
N3 N2 C12 O3 1.9(3) . . . . ?
N3 N2 C12 C11 -178.49(17) . . . . ?
N3 N2 C13 O4 -2.3(3) . . . . ?
N3 N2 C13 C10 -179.98(17) . . . . ?
N3 C16 C17 C18 177.5(2) . . . . ?
N3 C16 C21 C20 -178.89(17) . . . . ?
N3 C16 C21 C22 0.9(2) . . . . ?
N3 C23 C24 O5 -2.9(3) . . . . ?
N3 C23 C24 O6 -179.96(17) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C1 C6 C7 C8 -76.8(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C1 C6 C7 179.8(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 179.5(2) . . . . ?
C5 C6 C7 C8 103.8(3) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C6 C7 C8 N1 69.8(2) . . . . ?
C6 C7 C8 C11 -47.6(3) . . . . ?
C6 C7 C8 C14 -172.22(18) . . . . ?
C7 C8 C11 C10 108.48(18) . . . . ?
C7 C8 C11 C12 -136.56(18) . . . . ?
C7 C8 C14 O1 -141.5(2) . . . . ?
C7 C8 C14 O2 40.7(2) . . . . ?
C8 N1 C9 C10 -3.2(2) . . . . ?
C8 C11 C12 O3 65.8(3) . . . . ?
C8 C11 C12 N2 -113.81(18) . . . . ?
C9 N1 C8 C7 -112.5(2) . . . . ?
C9 N1 C8 C11 8.8(2) . . . . ?
C9 N1 C8 C14 127.30(18) . . . . ?
C9 C10 C11 C8 8.53(18) . . . . ?
C9 C10 C11 C12 -113.84(16) . . . . ?
C9 C10 C13 O4 -71.5(3) . . . . ?
C9 C10 C13 N2 106.04(18) . . . . ?
C10 C11 C12 O3 180.0(2) . . . . ?
C10 C11 C12 N2 0.35(19) . . . . ?
C11 C8 C14 O1 93.0(2) . . . . ?
C11 C8 C14 O2 -84.8(2) . . . . ?
C11 C10 C13 O4 178.2(2) . . . . ?
C11 C10 C13 N2 -4.3(2) . . . . ?
C12 N2 N3 C16 -93.7(2) . . . . ?
C12 N2 N3 C23 106.3(2) . . . . ?
C12 N2 C13 O4 -177.3(2) . . . . ?
C12 N2 C13 C10 5.0(2) . . . . ?
C13 N2 N3 C16 91.6(3) . . . . ?
C13 N2 N3 C23 -68.4(3) . . . . ?
C13 N2 C12 O3 176.93(19) . . . . ?
C13 N2 C12 C11 -3.4(2) . . . . ?
C13 C10 C11 C8 124.80(16) . . . . ?
C13 C10 C11 C12 2.4(2) . . . . ?
C14 C8 C11 C10 -126.84(16) . . . . ?
C14 C8 C11 C12 -11.9(2) . . . . ?
C15 O2 C14 O1 -4.9(3) . . . . ?
C15 O2 C14 C8 172.91(17) . . . . ?
C16 N3 C23 C22 1.5(2) . . . . ?
C16 N3 C23 C24 174.95(18) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C16 C21 C22 C23 0.0(2) . . . . ?
C17 C16 C21 C20 -1.7(3) . . . . ?
C17 C16 C21 C22 178.06(18) . . . . ?
C17 C18 C19 C20 -2.0(3) . . . . ?
C18 C19 C20 C21 1.3(3) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C19 C20 C21 C22 -179.2(2) . . . . ?
C20 C21 C22 C23 179.7(2) . . . . ?
C21 C16 C17 C18 1.0(3) . . . . ?
C21 C22 C23 N3 -0.9(2) . . . . ?
C21 C22 C23 C24 -173.4(2) . . . . ?
C22 C23 C24 O5 168.8(2) . . . . ?
C22 C23 C24 O6 -8.3(3) . . . . ?
C23 N3 C16 C17 -178.44(19) . . . . ?
C23 N3 C16 C21 -1.5(2) . . . . ?
C24 O6 C25 C26 -177.4(2) . . . . ?
C25 O6 C24 O5 -2.4(3) . . . . ?
C25 O6 C24 C23 174.71(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
