# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_m4279_0m
_database_code_depnum_ccdc_archive 'CCDC 2071227'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2020-09-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H28 N2 O5'
_chemical_formula_sum            'C36 H28 N2 O5'
_chemical_formula_weight         568.60
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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                   17.46(3)
_cell_length_b                   13.75(2)
_cell_length_c                   23.42(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5624(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4397
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.650
_cell_measurement_theta_min      2.568
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1345 before and 0.0821 after correction. The Ratio of minimum to maximum transmission is 0.8333. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38519
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         2.333
_diffrn_ambient_temperature      150.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                6628
_reflns_number_total             10995
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 2231 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       0.0065(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     776
_refine_ls_number_reflns         10995
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.021
_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)+(0.0659P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1575
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C19(H19), C8'(H8'), C9'(H9'), C19'(H19')
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C20(H20a,H20b), C16'(H16c,H16d), C20'(H20c,H20d)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C21(H21), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
  C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C1'(H1'), C2'(H2'),
 C3'(H3'), C4'(H4'), C5'(H5'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'),
 C17'(H17'), C21'(H21'), C25'(H25'), C26'(H26'), C27'(H27'), C28'(H28'),
 C29'(H29'), C32'(H32'), C33'(H33'), C34'(H34'), C35'(H35'), C36'(H36')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7675(3) 0.4004(4) 0.6371(3) 0.0340(15) Uani 1 1 d . . . . .
H1 H 0.7416 0.4573 0.6245 0.041 Uiso 1 1 calc R . . . .
C2 C 0.8466(3) 0.4021(5) 0.6458(3) 0.0407(17) Uani 1 1 d . . . . .
H2 H 0.8747 0.4603 0.6396 0.049 Uiso 1 1 calc R . . . .
C3 C 0.8838(3) 0.3186(5) 0.6634(3) 0.0375(16) Uani 1 1 d . . . . .
H3 H 0.9376 0.3197 0.6691 0.045 Uiso 1 1 calc R . . . .
C4 C 0.8444(3) 0.2349(5) 0.6725(3) 0.0379(16) Uani 1 1 d . . . . .
H4 H 0.8710 0.1781 0.6844 0.046 Uiso 1 1 calc R . . . .
C5 C 0.7657(3) 0.2315(5) 0.6648(3) 0.0375(16) Uani 1 1 d . . . . .
H5 H 0.7385 0.1728 0.6716 0.045 Uiso 1 1 calc R . . . .
C6 C 0.7264(3) 0.3148(4) 0.6469(3) 0.0302(14) Uani 1 1 d . . . . .
C7 C 0.6422(3) 0.3084(4) 0.6397(3) 0.0301(14) Uani 1 1 d . . . . .
C8 C 0.6040(3) 0.3701(4) 0.5947(3) 0.0288(14) Uani 1 1 d . . . . .
H8 H 0.6277 0.4362 0.5955 0.035 Uiso 1 1 calc R . . . .
C9 C 0.5180(3) 0.3809(4) 0.6069(3) 0.0325(15) Uani 1 1 d . . . . .
H9 H 0.4951 0.3150 0.6127 0.039 Uiso 1 1 calc R . . . .
C10 C 0.4957(3) 0.4464(4) 0.6566(3) 0.0330(15) Uani 1 1 d . . . . .
C11 C 0.5224(4) 0.4490(5) 0.7120(3) 0.0376(16) Uani 1 1 d . . . . .
H11 H 0.5604 0.4042 0.7243 0.045 Uiso 1 1 calc R . . . .
C12 C 0.4934(4) 0.5173(5) 0.7494(3) 0.0448(18) Uani 1 1 d . . . . .
H12 H 0.5128 0.5204 0.7873 0.054 Uiso 1 1 calc R . . . .
C13 C 0.4368(4) 0.5811(5) 0.7326(3) 0.0429(18) Uani 1 1 d . . . . .
H13 H 0.4167 0.6268 0.7591 0.052 Uiso 1 1 calc R . . . .
C14 C 0.4093(3) 0.5789(5) 0.6773(3) 0.0418(18) Uani 1 1 d . . . . .
H14 H 0.3705 0.6229 0.6654 0.050 Uiso 1 1 calc R . . . .
C15 C 0.4391(3) 0.5113(4) 0.6393(3) 0.0358(16) Uani 1 1 d . . . . .
C16 C 0.4180(3) 0.4961(5) 0.5777(3) 0.0418(18) Uani 1 1 d . . . . .
H16A H 0.3667 0.4662 0.5738 0.050 Uiso 1 1 calc R . . . .
H16B H 0.4194 0.5578 0.5559 0.050 Uiso 1 1 calc R . . . .
C17 C 0.5067(3) 0.4267(4) 0.5070(3) 0.0315(16) Uani 1 1 d . . . . .
H17 H 0.4798 0.4606 0.4779 0.038 Uiso 1 1 calc R . . . .
C18 C 0.5723(3) 0.3779(4) 0.4923(3) 0.0330(15) Uani 1 1 d . . . . .
C19 C 0.6201(3) 0.3241(4) 0.5353(3) 0.0310(15) Uani 1 1 d . . . . .
H19 H 0.6753 0.3348 0.5258 0.037 Uiso 1 1 calc R . . . .
C20 C 0.6045(3) 0.2131(4) 0.5352(3) 0.0330(15) Uani 1 1 d . . . . .
H20A H 0.6412 0.1817 0.5615 0.040 Uiso 1 1 calc R . . . .
H20B H 0.5524 0.2019 0.5506 0.040 Uiso 1 1 calc R . . . .
C21 C 0.6101(3) 0.1640(4) 0.4782(3) 0.0324(15) Uani 1 1 d . . . . .
H21 H 0.6583 0.1647 0.4594 0.039 Uiso 1 1 calc R . . . .
C22 C 0.5518(3) 0.1192(4) 0.4521(3) 0.0328(16) Uani 1 1 d . . . . .
C23 C 0.5597(4) 0.0591(4) 0.3991(3) 0.0407(17) Uani 1 1 d . . . . .
C24 C 0.6218(3) 0.0757(5) 0.3575(3) 0.0392(17) Uani 1 1 d . . . . .
C25 C 0.6507(4) -0.0045(5) 0.3277(3) 0.050(2) Uani 1 1 d . . . . .
H25 H 0.6321 -0.0680 0.3356 0.060 Uiso 1 1 calc R . . . .
C26 C 0.7067(5) 0.0092(6) 0.2866(4) 0.062(2) Uani 1 1 d . . . . .
H26 H 0.7275 -0.0453 0.2671 0.074 Uiso 1 1 calc R . . . .
C27 C 0.7327(4) 0.1014(7) 0.2736(4) 0.065(2) Uani 1 1 d . . . . .
H27 H 0.7708 0.1101 0.2451 0.077 Uiso 1 1 calc R . . . .
C28 C 0.7033(4) 0.1814(6) 0.3022(4) 0.059(2) Uani 1 1 d . . . . .
H28 H 0.7207 0.2448 0.2929 0.071 Uiso 1 1 calc R . . . .
C29 C 0.6481(4) 0.1686(5) 0.3446(3) 0.0476(19) Uani 1 1 d . . . . .
H29 H 0.6285 0.2233 0.3646 0.057 Uiso 1 1 calc R . . . .
C30 C 0.4735(3) 0.1196(5) 0.4792(3) 0.0386(16) Uani 1 1 d . . . . .
C31 C 0.4209(3) 0.2006(4) 0.4632(3) 0.0351(16) Uani 1 1 d . . . . .
C32 C 0.3639(3) 0.2297(5) 0.5011(3) 0.0463(19) Uani 1 1 d . . . . .
H32 H 0.3573 0.1962 0.5362 0.056 Uiso 1 1 calc R . . . .
C33 C 0.3172(3) 0.3068(6) 0.4878(4) 0.056(2) Uani 1 1 d . . . . .
H33 H 0.2792 0.3275 0.5141 0.067 Uiso 1 1 calc R . . . .
C34 C 0.3254(4) 0.3544(5) 0.4362(4) 0.053(2) Uani 1 1 d . . . . .
H34 H 0.2926 0.4073 0.4271 0.064 Uiso 1 1 calc R . . . .
C35 C 0.3807(3) 0.3258(5) 0.3977(4) 0.0468(18) Uani 1 1 d . . . . .
H35 H 0.3851 0.3576 0.3618 0.056 Uiso 1 1 calc R . . . .
C36 C 0.4301(3) 0.2501(5) 0.4117(3) 0.0382(16) Uani 1 1 d . . . . .
H36 H 0.4701 0.2322 0.3863 0.046 Uiso 1 1 calc R . . . .
N1 N 0.4790(2) 0.4292(4) 0.5593(3) 0.0329(13) Uani 1 1 d . . . . .
N2 N 0.5988(3) 0.3835(4) 0.4363(3) 0.0371(14) Uani 1 1 d . . . . .
O1 O 0.6047(2) 0.2479(3) 0.6672(2) 0.0369(11) Uani 1 1 d . . . . .
O2 O 0.5560(3) 0.4181(3) 0.3976(2) 0.0473(12) Uani 1 1 d . . . . .
O3 O 0.6638(3) 0.3534(3) 0.4245(2) 0.0443(12) Uani 1 1 d . . . . .
O4 O 0.5124(3) -0.0072(3) 0.3914(2) 0.0567(14) Uani 1 1 d . . . . .
O5 O 0.4558(3) 0.0584(4) 0.5146(2) 0.0549(14) Uani 1 1 d . . . . .
C1' C 0.4671(3) 0.7823(5) 0.3142(3) 0.0385(16) Uani 1 1 d . . . . .
H1' H 0.4989 0.8346 0.3024 0.046 Uiso 1 1 calc R . . . .
C2' C 0.3896(3) 0.7852(5) 0.3029(3) 0.0411(17) Uani 1 1 d . . . . .
H2' H 0.3683 0.8399 0.2839 0.049 Uiso 1 1 calc R . . . .
C3' C 0.3435(3) 0.7097(5) 0.3188(3) 0.0414(17) Uani 1 1 d . . . . .
H3' H 0.2905 0.7110 0.3096 0.050 Uiso 1 1 calc R . . . .
C4' C 0.3738(3) 0.6309(5) 0.3487(3) 0.0388(16) Uani 1 1 d . . . . .
H4' H 0.3416 0.5789 0.3603 0.047 Uiso 1 1 calc R . . . .
C5' C 0.4521(3) 0.6292(4) 0.3612(3) 0.0328(15) Uani 1 1 d . . . . .
H5' H 0.4732 0.5769 0.3825 0.039 Uiso 1 1 calc R . . . .
C6' C 0.4989(3) 0.7041(4) 0.3425(3) 0.0274(14) Uani 1 1 d . . . . .
C7' C 0.5838(3) 0.7031(4) 0.3510(3) 0.0276(14) Uani 1 1 d . . . . .
C8' C 0.6176(3) 0.6407(4) 0.3985(3) 0.0250(13) Uani 1 1 d . . . . .
H8' H 0.5939 0.5745 0.3967 0.030 Uiso 1 1 calc R . . . .
C9' C 0.7044(3) 0.6305(4) 0.3920(3) 0.0258(13) Uani 1 1 d . . . . .
H9' H 0.7280 0.6964 0.3880 0.031 Uiso 1 1 calc R . . . .
C10' C 0.7331(3) 0.5647(4) 0.3440(3) 0.0257(13) Uani 1 1 d . . . . .
C11' C 0.7144(3) 0.5656(4) 0.2868(3) 0.0325(15) Uani 1 1 d . . . . .
H11' H 0.6771 0.6097 0.2726 0.039 Uiso 1 1 calc R . . . .
C12' C 0.7510(3) 0.5011(4) 0.2504(3) 0.0345(15) Uani 1 1 d . . . . .
H12' H 0.7384 0.5007 0.2110 0.041 Uiso 1 1 calc R . . . .
C13' C 0.8056(3) 0.4374(5) 0.2710(3) 0.0395(17) Uani 1 1 d . . . . .
H13' H 0.8303 0.3936 0.2456 0.047 Uiso 1 1 calc R . . . .
C14' C 0.8247(3) 0.4369(5) 0.3281(3) 0.0371(16) Uani 1 1 d . . . . .
H14' H 0.8621 0.3929 0.3423 0.045 Uiso 1 1 calc R . . . .
C15' C 0.7884(3) 0.5016(4) 0.3643(3) 0.0313(15) Uani 1 1 d . . . . .
C16' C 0.8003(3) 0.5137(5) 0.4275(3) 0.0370(16) Uani 1 1 d . . . . .
H16C H 0.7955 0.4509 0.4478 0.044 Uiso 1 1 calc R . . . .
H16D H 0.8510 0.5426 0.4359 0.044 Uiso 1 1 calc R . . . .
C17' C 0.7052(3) 0.5848(4) 0.4938(3) 0.0299(15) Uani 1 1 d . . . . .
H17' H 0.7284 0.5515 0.5248 0.036 Uiso 1 1 calc R . . . .
C18' C 0.6399(3) 0.6353(4) 0.5029(3) 0.0273(14) Uani 1 1 d . . . . .
C19' C 0.5966(3) 0.6883(4) 0.4573(3) 0.0253(13) Uani 1 1 d . . . . .
H19' H 0.5406 0.6788 0.4641 0.030 Uiso 1 1 calc R . . . .
C20' C 0.6135(3) 0.7997(4) 0.4567(3) 0.0308(15) Uani 1 1 d . . . . .
H20C H 0.6650 0.8099 0.4401 0.037 Uiso 1 1 calc R . . . .
H20D H 0.5761 0.8314 0.4309 0.037 Uiso 1 1 calc R . . . .
C21' C 0.6104(3) 0.8497(4) 0.5132(3) 0.0282(14) Uani 1 1 d . . . . .
H21' H 0.5621 0.8542 0.5316 0.034 Uiso 1 1 calc R . . . .
C22' C 0.6705(3) 0.8883(4) 0.5397(3) 0.0282(15) Uani 1 1 d . . . . .
C23' C 0.6649(3) 0.9494(4) 0.5917(3) 0.0318(15) Uani 1 1 d . . . . .
C24' C 0.6028(3) 0.9307(4) 0.6347(3) 0.0301(15) Uani 1 1 d . . . . .
C25' C 0.5798(3) 0.8371(5) 0.6475(3) 0.0364(16) Uani 1 1 d . . . . .
H25' H 0.6011 0.7838 0.6271 0.044 Uiso 1 1 calc R . . . .
C26' C 0.5263(4) 0.8203(5) 0.6896(3) 0.0448(18) Uani 1 1 d . . . . .
H26' H 0.5119 0.7557 0.6989 0.054 Uiso 1 1 calc R . . . .
C27' C 0.4937(4) 0.8975(6) 0.7181(3) 0.0465(19) Uani 1 1 d . . . . .
H27' H 0.4552 0.8861 0.7460 0.056 Uiso 1 1 calc R . . . .
C28' C 0.5167(4) 0.9913(6) 0.7063(3) 0.0451(18) Uani 1 1 d . . . . .
H28' H 0.4953 1.0442 0.7269 0.054 Uiso 1 1 calc R . . . .
C29' C 0.5708(3) 1.0083(5) 0.6644(3) 0.0382(16) Uani 1 1 d . . . . .
H29' H 0.5862 1.0730 0.6560 0.046 Uiso 1 1 calc R . . . .
C30' C 0.7493(3) 0.8810(4) 0.5127(3) 0.0295(14) Uani 1 1 d . . . . .
C31' C 0.7990(3) 0.7996(4) 0.5325(3) 0.0290(14) Uani 1 1 d . . . . .
C32' C 0.8569(3) 0.7656(5) 0.4959(3) 0.0356(16) Uani 1 1 d . . . . .
H32' H 0.8648 0.7958 0.4599 0.043 Uiso 1 1 calc R . . . .
C33' C 0.9019(3) 0.6888(5) 0.5122(3) 0.0398(18) Uani 1 1 d . . . . .
H33' H 0.9394 0.6641 0.4866 0.048 Uiso 1 1 calc R . . . .
C34' C 0.8932(3) 0.6469(5) 0.5656(3) 0.0408(17) Uani 1 1 d . . . . .
H34' H 0.9262 0.5956 0.5771 0.049 Uiso 1 1 calc R . . . .
C35' C 0.8364(3) 0.6797(4) 0.6023(3) 0.0386(16) Uani 1 1 d . . . . .
H35' H 0.8299 0.6503 0.6387 0.046 Uiso 1 1 calc R . . . .
C36' C 0.7893(3) 0.7553(4) 0.5856(3) 0.0320(15) Uani 1 1 d . . . . .
H36' H 0.7501 0.7773 0.6105 0.038 Uiso 1 1 calc R . . . .
N1' N 0.7375(3) 0.5806(3) 0.4427(2) 0.0302(12) Uani 1 1 d . . . . .
N2' N 0.6085(3) 0.6320(3) 0.5582(2) 0.0314(13) Uani 1 1 d . . . . .
O1' O 0.6256(2) 0.7565(3) 0.32254(19) 0.0357(11) Uani 1 1 d . . . . .
O2' O 0.6464(2) 0.5993(3) 0.5993(2) 0.0380(11) Uani 1 1 d . . . . .
O3' O 0.5413(2) 0.6630(3) 0.56540(19) 0.0369(11) Uani 1 1 d . . . . .
O4' O 0.7111(2) 1.0153(3) 0.5990(2) 0.0440(12) Uani 1 1 d . . . . .
O5' O 0.7692(2) 0.9360(3) 0.4745(2) 0.0495(13) 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 H1 0.9500 . ?
C1 C2 1.396(8) . ?
C1 C6 1.398(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.358(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(8) . ?
C6 C7 1.481(8) . ?
C7 C8 1.510(8) . ?
C7 O1 1.240(7) . ?
C8 H8 1.0000 . ?
C8 C9 1.535(8) . ?
C8 C19 1.553(9) . ?
C9 H9 1.0000 . ?
C9 C10 1.524(9) . ?
C9 N1 1.466(8) . ?
C10 C11 1.378(10) . ?
C10 C15 1.393(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(9) . ?
C15 C16 1.504(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N1 1.472(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.372(9) . ?
C17 N1 1.317(9) . ?
C18 C19 1.502(9) . ?
C18 N2 1.392(9) . ?
C19 H19 1.0000 . ?
C19 C20 1.551(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.498(10) . ?
C21 H21 0.9500 . ?
C21 C22 1.338(8) . ?
C22 C23 1.499(10) . ?
C22 C30 1.507(9) . ?
C23 C24 1.475(10) . ?
C23 O4 1.242(7) . ?
C24 C25 1.400(9) . ?
C24 C29 1.392(9) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(11) . ?
C26 H26 0.9500 . ?
C26 C27 1.380(11) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(12) . ?
C28 H28 0.9500 . ?
C28 C29 1.396(10) . ?
C29 H29 0.9500 . ?
C30 C31 1.491(9) . ?
C30 O5 1.221(8) . ?
C31 C32 1.391(9) . ?
C31 C36 1.395(10) . ?
C32 H32 0.9500 . ?
C32 C33 1.372(10) . ?
C33 H33 0.9500 . ?
C33 C34 1.383(11) . ?
C34 H34 0.9500 . ?
C34 C35 1.378(10) . ?
C35 H35 0.9500 . ?
C35 C36 1.392(9) . ?
C36 H36 0.9500 . ?
N2 O2 1.268(7) . ?
N2 O3 1.239(7) . ?
C1' H1' 0.9500 . ?
C1' C2' 1.379(8) . ?
C1' C6' 1.379(8) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.366(9) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.394(9) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.398(8) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.386(8) . ?
C6' C7' 1.496(8) . ?
C7' C8' 1.525(8) . ?
C7' O1' 1.231(7) . ?
C8' H8' 1.0000 . ?
C8' C9' 1.530(7) . ?
C8' C19' 1.567(9) . ?
C9' H9' 1.0000 . ?
C9' C10' 1.525(9) . ?
C9' N1' 1.489(8) . ?
C10' C11' 1.379(9) . ?
C10' C15' 1.382(8) . ?
C11' H11' 0.9500 . ?
C11' C12' 1.387(9) . ?
C12' H12' 0.9500 . ?
C12' C13' 1.382(9) . ?
C13' H13' 0.9500 . ?
C13' C14' 1.378(10) . ?
C14' H14' 0.9500 . ?
C14' C15' 1.384(9) . ?
C15' C16' 1.504(10) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C16' N1' 1.476(7) . ?
C17' H17' 0.9500 . ?
C17' C18' 1.351(8) . ?
C17' N1' 1.322(8) . ?
C18' C19' 1.498(8) . ?
C18' N2' 1.408(8) . ?
C19' H19' 1.0000 . ?
C19' C20' 1.560(8) . ?
C20' H20C 0.9900 . ?
C20' H20D 0.9900 . ?
C20' C21' 1.493(9) . ?
C21' H21' 0.9500 . ?
C21' C22' 1.329(8) . ?
C22' C23' 1.484(9) . ?
C22' C30' 1.517(8) . ?
C23' C24' 1.502(9) . ?
C23' O4' 1.226(7) . ?
C24' C25' 1.381(8) . ?
C24' C29' 1.393(9) . ?
C25' H25' 0.9500 . ?
C25' C26' 1.378(9) . ?
C26' H26' 0.9500 . ?
C26' C27' 1.377(10) . ?
C27' H27' 0.9500 . ?
C27' C28' 1.379(11) . ?
C28' H28' 0.9500 . ?
C28' C29' 1.381(10) . ?
C29' H29' 0.9500 . ?
C30' C31' 1.491(8) . ?
C30' O5' 1.221(8) . ?
C31' C32' 1.407(8) . ?
C31' C36' 1.395(9) . ?
C32' H32' 0.9500 . ?
C32' C33' 1.371(9) . ?
C33' H33' 0.9500 . ?
C33' C34' 1.386(10) . ?
C34' H34' 0.9500 . ?
C34' C35' 1.388(9) . ?
C35' H35' 0.9500 . ?
C35' C36' 1.382(8) . ?
C36' H36' 0.9500 . ?
N2' O2' 1.251(7) . ?
N2' O3' 1.260(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.8(6) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(6) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(6) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.2(5) . . ?
C1 C6 C7 122.7(5) . . ?
C5 C6 C7 118.1(5) . . ?
C6 C7 C8 119.0(5) . . ?
O1 C7 C6 120.3(5) . . ?
O1 C7 C8 120.5(5) . . ?
C7 C8 H8 108.3 . . ?
C7 C8 C9 110.9(5) . . ?
C7 C8 C19 108.4(5) . . ?
C9 C8 H8 108.3 . . ?
C9 C8 C19 112.6(5) . . ?
C19 C8 H8 108.3 . . ?
C8 C9 H9 109.2 . . ?
C10 C9 C8 116.7(5) . . ?
C10 C9 H9 109.2 . . ?
N1 C9 C8 110.9(5) . . ?
N1 C9 H9 109.2 . . ?
N1 C9 C10 101.2(5) . . ?
C11 C10 C9 130.4(6) . . ?
C11 C10 C15 119.9(6) . . ?
C15 C10 C9 109.7(6) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(6) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(7) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(7) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(6) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C16 111.4(6) . . ?
C14 C15 C10 120.5(7) . . ?
C14 C15 C16 128.1(6) . . ?
C15 C16 H16A 111.6 . . ?
C15 C16 H16B 111.6 . . ?
H16A C16 H16B 109.4 . . ?
N1 C16 C15 101.0(5) . . ?
N1 C16 H16A 111.6 . . ?
N1 C16 H16B 111.6 . . ?
C18 C17 H17 118.2 . . ?
N1 C17 H17 118.2 . . ?
N1 C17 C18 123.5(6) . . ?
C17 C18 C19 122.4(6) . . ?
C17 C18 N2 119.1(6) . . ?
N2 C18 C19 118.3(6) . . ?
C8 C19 H19 108.3 . . ?
C18 C19 C8 107.4(5) . . ?
C18 C19 H19 108.3 . . ?
C18 C19 C20 112.7(5) . . ?
C20 C19 C8 111.7(5) . . ?
C20 C19 H19 108.3 . . ?
C19 C20 H20A 108.4 . . ?
C19 C20 H20B 108.4 . . ?
H20A C20 H20B 107.4 . . ?
C21 C20 C19 115.7(5) . . ?
C21 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C20 C21 H21 117.8 . . ?
C22 C21 C20 124.4(6) . . ?
C22 C21 H21 117.8 . . ?
C21 C22 C23 124.3(6) . . ?
C21 C22 C30 119.8(6) . . ?
C23 C22 C30 115.7(5) . . ?
C24 C23 C22 121.9(6) . . ?
O4 C23 C22 117.7(6) . . ?
O4 C23 C24 120.3(7) . . ?
C25 C24 C23 118.2(6) . . ?
C29 C24 C23 121.9(6) . . ?
C29 C24 C25 119.7(7) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(7) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.7(8) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.1(8) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0(8) . . ?
C29 C28 H28 120.0 . . ?
C24 C29 C28 119.9(7) . . ?
C24 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C22 117.1(6) . . ?
O5 C30 C22 120.9(6) . . ?
O5 C30 C31 121.9(6) . . ?
C32 C31 C30 119.8(7) . . ?
C32 C31 C36 119.5(6) . . ?
C36 C31 C30 120.7(6) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.2(8) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.1(7) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.7(7) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 120.2 . . ?
C34 C35 C36 119.5(8) . . ?
C36 C35 H35 120.2 . . ?
C31 C36 H36 120.1 . . ?
C35 C36 C31 119.9(6) . . ?
C35 C36 H36 120.1 . . ?
C9 N1 C16 113.4(6) . . ?
C17 N1 C9 121.7(5) . . ?
C17 N1 C16 123.6(5) . . ?
O2 N2 C18 120.0(6) . . ?
O3 N2 C18 119.7(6) . . ?
O3 N2 O2 120.3(6) . . ?
C2' C1' H1' 119.7 . . ?
C2' C1' C6' 120.6(6) . . ?
C6' C1' H1' 119.7 . . ?
C1' C2' H2' 119.9 . . ?
C3' C2' C1' 120.2(6) . . ?
C3' C2' H2' 119.9 . . ?
C2' C3' H3' 119.9 . . ?
C2' C3' C4' 120.3(6) . . ?
C4' C3' H3' 119.9 . . ?
C3' C4' H4' 120.4 . . ?
C3' C4' C5' 119.3(6) . . ?
C5' C4' H4' 120.4 . . ?
C4' C5' H5' 120.1 . . ?
C6' C5' C4' 119.8(6) . . ?
C6' C5' H5' 120.1 . . ?
C1' C6' C5' 119.6(5) . . ?
C1' C6' C7' 118.1(5) . . ?
C5' C6' C7' 122.3(5) . . ?
C6' C7' C8' 119.1(5) . . ?
O1' C7' C6' 120.6(6) . . ?
O1' C7' C8' 120.2(5) . . ?
C7' C8' H8' 108.8 . . ?
C7' C8' C9' 111.2(5) . . ?
C7' C8' C19' 108.4(5) . . ?
C9' C8' H8' 108.8 . . ?
C9' C8' C19' 111.0(5) . . ?
C19' C8' H8' 108.8 . . ?
C8' C9' H9' 109.5 . . ?
C10' C9' C8' 116.9(5) . . ?
C10' C9' H9' 109.5 . . ?
N1' C9' C8' 110.2(5) . . ?
N1' C9' H9' 109.5 . . ?
N1' C9' C10' 100.8(5) . . ?
C11' C10' C9' 129.2(5) . . ?
C11' C10' C15' 120.3(6) . . ?
C15' C10' C9' 110.4(6) . . ?
C10' C11' H11' 120.6 . . ?
C10' C11' C12' 118.9(6) . . ?
C12' C11' H11' 120.6 . . ?
C11' C12' H12' 119.7 . . ?
C13' C12' C11' 120.6(7) . . ?
C13' C12' H12' 119.7 . . ?
C12' C13' H13' 119.7 . . ?
C14' C13' C12' 120.6(6) . . ?
C14' C13' H13' 119.7 . . ?
C13' C14' H14' 120.7 . . ?
C13' C14' C15' 118.7(6) . . ?
C15' C14' H14' 120.7 . . ?
C10' C15' C14' 120.9(6) . . ?
C10' C15' C16' 111.4(5) . . ?
C14' C15' C16' 127.6(6) . . ?
C15' C16' H16C 111.4 . . ?
C15' C16' H16D 111.4 . . ?
H16C C16' H16D 109.3 . . ?
N1' C16' C15' 101.8(5) . . ?
N1' C16' H16C 111.4 . . ?
N1' C16' H16D 111.4 . . ?
C18' C17' H17' 119.2 . . ?
N1' C17' H17' 119.2 . . ?
N1' C17' C18' 121.7(6) . . ?
C17' C18' C19' 124.2(6) . . ?
C17' C18' N2' 117.2(6) . . ?
N2' C18' C19' 118.5(5) . . ?
C8' C19' H19' 108.3 . . ?
C18' C19' C8' 107.8(5) . . ?
C18' C19' H19' 108.3 . . ?
C18' C19' C20' 112.9(5) . . ?
C20' C19' C8' 111.0(5) . . ?
C20' C19' H19' 108.3 . . ?
C19' C20' H20C 108.3 . . ?
C19' C20' H20D 108.3 . . ?
H20C C20' H20D 107.4 . . ?
C21' C20' C19' 115.9(5) . . ?
C21' C20' H20C 108.3 . . ?
C21' C20' H20D 108.3 . . ?
C20' C21' H21' 117.6 . . ?
C22' C21' C20' 124.7(5) . . ?
C22' C21' H21' 117.6 . . ?
C21' C22' C23' 123.9(5) . . ?
C21' C22' C30' 119.6(6) . . ?
C23' C22' C30' 116.1(5) . . ?
C22' C23' C24' 120.1(5) . . ?
O4' C23' C22' 119.3(6) . . ?
O4' C23' C24' 120.6(6) . . ?
C25' C24' C23' 121.0(6) . . ?
C25' C24' C29' 119.4(6) . . ?
C29' C24' C23' 119.6(5) . . ?
C24' C25' H25' 119.7 . . ?
C26' C25' C24' 120.5(6) . . ?
C26' C25' H25' 119.7 . . ?
C25' C26' H26' 120.1 . . ?
C27' C26' C25' 119.9(7) . . ?
C27' C26' H26' 120.1 . . ?
C26' C27' H27' 119.9 . . ?
C26' C27' C28' 120.3(7) . . ?
C28' C27' H27' 119.9 . . ?
C27' C28' H28' 120.0 . . ?
C27' C28' C29' 120.0(7) . . ?
C29' C28' H28' 120.0 . . ?
C24' C29' H29' 120.0 . . ?
C28' C29' C24' 119.9(6) . . ?
C28' C29' H29' 120.0 . . ?
C31' C30' C22' 116.6(5) . . ?
O5' C30' C22' 121.4(5) . . ?
O5' C30' C31' 121.9(5) . . ?
C32' C31' C30' 118.5(6) . . ?
C36' C31' C30' 122.4(6) . . ?
C36' C31' C32' 119.1(6) . . ?
C31' C32' H32' 120.1 . . ?
C33' C32' C31' 119.9(6) . . ?
C33' C32' H32' 120.1 . . ?
C32' C33' H33' 119.7 . . ?
C32' C33' C34' 120.6(6) . . ?
C34' C33' H33' 119.7 . . ?
C33' C34' H34' 119.9 . . ?
C33' C34' C35' 120.2(6) . . ?
C35' C34' H34' 119.9 . . ?
C34' C35' H35' 120.2 . . ?
C36' C35' C34' 119.6(7) . . ?
C36' C35' H35' 120.2 . . ?
C31' C36' H36' 119.7 . . ?
C35' C36' C31' 120.6(6) . . ?
C35' C36' H36' 119.7 . . ?
C16' N1' C9' 112.4(5) . . ?
C17' N1' C9' 122.4(5) . . ?
C17' N1' C16' 124.3(5) . . ?
O2' N2' C18' 121.0(5) . . ?
O2' N2' O3' 120.7(5) . . ?
O3' N2' C18' 118.3(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
C1 C2 C3 C4 -0.2(11) . . . . ?
C1 C6 C7 C8 32.1(9) . . . . ?
C1 C6 C7 O1 -153.3(6) . . . . ?
C2 C1 C6 C5 -0.7(10) . . . . ?
C2 C1 C6 C7 178.7(6) . . . . ?
C2 C3 C4 C5 -0.4(11) . . . . ?
C3 C4 C5 C6 0.5(10) . . . . ?
C4 C5 C6 C1 0.0(10) . . . . ?
C4 C5 C6 C7 -179.4(6) . . . . ?
C5 C6 C7 C8 -148.5(6) . . . . ?
C5 C6 C7 O1 26.1(9) . . . . ?
C6 C1 C2 C3 0.8(11) . . . . ?
C6 C7 C8 C9 -160.4(5) . . . . ?
C6 C7 C8 C19 75.5(6) . . . . ?
C7 C8 C9 C10 72.7(7) . . . . ?
C7 C8 C9 N1 -172.2(5) . . . . ?
C7 C8 C19 C18 171.9(5) . . . . ?
C7 C8 C19 C20 47.9(6) . . . . ?
C8 C9 C10 C11 -49.3(9) . . . . ?
C8 C9 C10 C15 130.9(5) . . . . ?
C8 C9 N1 C16 -142.6(5) . . . . ?
C8 C9 N1 C17 24.8(7) . . . . ?
C8 C19 C20 C21 173.6(5) . . . . ?
C9 C8 C19 C18 48.8(6) . . . . ?
C9 C8 C19 C20 -75.2(6) . . . . ?
C9 C10 C11 C12 179.0(6) . . . . ?
C9 C10 C15 C14 -180.0(5) . . . . ?
C9 C10 C15 C16 0.1(7) . . . . ?
C10 C9 N1 C16 -18.1(6) . . . . ?
C10 C9 N1 C17 149.3(5) . . . . ?
C10 C11 C12 C13 1.7(10) . . . . ?
C10 C15 C16 N1 -10.6(6) . . . . ?
C11 C10 C15 C14 0.1(9) . . . . ?
C11 C10 C15 C16 -179.8(6) . . . . ?
C11 C12 C13 C14 -1.4(10) . . . . ?
C12 C13 C14 C15 0.4(10) . . . . ?
C13 C14 C15 C10 0.2(9) . . . . ?
C13 C14 C15 C16 -179.9(6) . . . . ?
C14 C15 C16 N1 169.5(6) . . . . ?
C15 C10 C11 C12 -1.1(9) . . . . ?
C15 C16 N1 C9 18.1(6) . . . . ?
C15 C16 N1 C17 -149.0(5) . . . . ?
C17 C18 C19 C8 -24.0(7) . . . . ?
C17 C18 C19 C20 99.5(7) . . . . ?
C17 C18 N2 O2 -12.6(8) . . . . ?
C17 C18 N2 O3 168.3(5) . . . . ?
C18 C17 N1 C9 1.5(9) . . . . ?
C18 C17 N1 C16 167.6(5) . . . . ?
C18 C19 C20 C21 52.5(7) . . . . ?
C19 C8 C9 C10 -165.6(5) . . . . ?
C19 C8 C9 N1 -50.5(6) . . . . ?
C19 C18 N2 O2 171.7(5) . . . . ?
C19 C18 N2 O3 -7.4(8) . . . . ?
C19 C20 C21 C22 -117.5(7) . . . . ?
C20 C21 C22 C23 -171.6(6) . . . . ?
C20 C21 C22 C30 2.4(9) . . . . ?
C21 C22 C23 C24 -26.6(9) . . . . ?
C21 C22 C23 O4 152.2(6) . . . . ?
C21 C22 C30 C31 91.0(8) . . . . ?
C21 C22 C30 O5 -85.7(8) . . . . ?
C22 C23 C24 C25 147.6(6) . . . . ?
C22 C23 C24 C29 -36.9(9) . . . . ?
C22 C30 C31 C32 -153.4(6) . . . . ?
C22 C30 C31 C36 23.9(9) . . . . ?
C23 C22 C30 C31 -94.6(7) . . . . ?
C23 C22 C30 O5 88.8(8) . . . . ?
C23 C24 C25 C26 177.2(6) . . . . ?
C23 C24 C29 C28 -175.6(6) . . . . ?
C24 C25 C26 C27 -1.8(11) . . . . ?
C25 C24 C29 C28 -0.2(10) . . . . ?
C25 C26 C27 C28 0.5(12) . . . . ?
C26 C27 C28 C29 0.9(12) . . . . ?
C27 C28 C29 C24 -1.0(11) . . . . ?
C29 C24 C25 C26 1.6(10) . . . . ?
C30 C22 C23 C24 159.2(6) . . . . ?
C30 C22 C23 O4 -21.9(8) . . . . ?
C30 C31 C32 C33 177.3(6) . . . . ?
C30 C31 C36 C35 -179.7(5) . . . . ?
C31 C32 C33 C34 1.5(10) . . . . ?
C32 C31 C36 C35 -2.3(9) . . . . ?
C32 C33 C34 C35 -0.5(11) . . . . ?
C33 C34 C35 C36 -1.8(10) . . . . ?
C34 C35 C36 C31 3.2(9) . . . . ?
C36 C31 C32 C33 -0.1(9) . . . . ?
N1 C9 C10 C11 -169.7(6) . . . . ?
N1 C9 C10 C15 10.5(6) . . . . ?
N1 C17 C18 C19 -1.5(9) . . . . ?
N1 C17 C18 N2 -177.0(5) . . . . ?
N2 C18 C19 C8 151.6(5) . . . . ?
N2 C18 C19 C20 -84.9(7) . . . . ?
O1 C7 C8 C9 25.0(8) . . . . ?
O1 C7 C8 C19 -99.1(6) . . . . ?
O4 C23 C24 C25 -31.3(9) . . . . ?
O4 C23 C24 C29 144.2(6) . . . . ?
O5 C30 C31 C32 23.2(9) . . . . ?
O5 C30 C31 C36 -159.4(6) . . . . ?
C1' C2' C3' C4' 2.5(10) . . . . ?
C1' C6' C7' C8' 158.3(6) . . . . ?
C1' C6' C7' O1' -17.0(9) . . . . ?
C2' C1' C6' C5' -2.0(10) . . . . ?
C2' C1' C6' C7' 177.1(6) . . . . ?
C2' C3' C4' C5' -1.0(10) . . . . ?
C3' C4' C5' C6' -2.0(10) . . . . ?
C4' C5' C6' C1' 3.4(9) . . . . ?
C4' C5' C6' C7' -175.6(6) . . . . ?
C5' C6' C7' C8' -22.6(9) . . . . ?
C5' C6' C7' O1' 162.0(6) . . . . ?
C6' C1' C2' C3' -1.0(10) . . . . ?
C6' C7' C8' C9' 166.9(5) . . . . ?
C6' C7' C8' C19' -70.9(6) . . . . ?
C7' C8' C9' C10' -73.2(6) . . . . ?
C7' C8' C9' N1' 172.5(5) . . . . ?
C7' C8' C19' C18' -171.5(4) . . . . ?
C7' C8' C19' C20' -47.4(6) . . . . ?
C8' C9' C10' C11' 52.2(8) . . . . ?
C8' C9' C10' C15' -131.8(5) . . . . ?
C8' C9' N1' C16' 142.2(5) . . . . ?
C8' C9' N1' C17' -27.5(8) . . . . ?
C8' C19' C20' C21' -168.5(5) . . . . ?
C9' C8' C19' C18' -49.2(6) . . . . ?
C9' C8' C19' C20' 75.0(6) . . . . ?
C9' C10' C11' C12' 176.8(5) . . . . ?
C9' C10' C15' C14' -177.9(5) . . . . ?
C9' C10' C15' C16' 2.9(6) . . . . ?
C10' C9' N1' C16' 18.1(6) . . . . ?
C10' C9' N1' C17' -151.7(5) . . . . ?
C10' C11' C12' C13' -0.4(8) . . . . ?
C10' C15' C16' N1' 8.1(6) . . . . ?
C11' C10' C15' C14' -1.5(8) . . . . ?
C11' C10' C15' C16' 179.3(5) . . . . ?
C11' C12' C13' C14' 0.0(9) . . . . ?
C12' C13' C14' C15' -0.3(9) . . . . ?
C13' C14' C15' C10' 1.1(9) . . . . ?
C13' C14' C15' C16' -179.9(6) . . . . ?
C14' C15' C16' N1' -171.1(6) . . . . ?
C15' C10' C11' C12' 1.1(8) . . . . ?
C15' C16' N1' C9' -16.7(6) . . . . ?
C15' C16' N1' C17' 152.9(5) . . . . ?
C17' C18' C19' C8' 23.5(7) . . . . ?
C17' C18' C19' C20' -99.4(7) . . . . ?
C17' C18' N2' O2' 12.8(8) . . . . ?
C17' C18' N2' O3' -167.2(5) . . . . ?
C18' C17' N1' C9' -0.2(9) . . . . ?
C18' C17' N1' C16' -168.7(5) . . . . ?
C18' C19' C20' C21' -47.4(7) . . . . ?
C19' C8' C9' C10' 166.1(5) . . . . ?
C19' C8' C9' N1' 51.8(6) . . . . ?
C19' C18' N2' O2' -171.1(5) . . . . ?
C19' C18' N2' O3' 8.8(7) . . . . ?
C19' C20' C21' C22' 113.0(7) . . . . ?
C20' C21' C22' C23' 171.2(6) . . . . ?
C20' C21' C22' C30' -1.4(9) . . . . ?
C21' C22' C23' C24' 32.6(9) . . . . ?
C21' C22' C23' O4' -147.0(6) . . . . ?
C21' C22' C30' C31' -96.1(7) . . . . ?
C21' C22' C30' O5' 80.1(8) . . . . ?
C22' C23' C24' C25' 37.6(9) . . . . ?
C22' C23' C24' C29' -146.1(6) . . . . ?
C22' C30' C31' C32' 155.4(5) . . . . ?
C22' C30' C31' C36' -23.6(8) . . . . ?
C23' C22' C30' C31' 90.7(7) . . . . ?
C23' C22' C30' O5' -93.0(7) . . . . ?
C23' C24' C25' C26' 175.8(6) . . . . ?
C23' C24' C29' C28' -176.4(6) . . . . ?
C24' C25' C26' C27' 1.8(10) . . . . ?
C25' C24' C29' C28' -0.1(10) . . . . ?
C25' C26' C27' C28' -2.6(10) . . . . ?
C26' C27' C28' C29' 2.1(10) . . . . ?
C27' C28' C29' C24' -0.7(10) . . . . ?
C29' C24' C25' C26' -0.5(10) . . . . ?
C30' C22' C23' C24' -154.6(5) . . . . ?
C30' C22' C23' O4' 25.8(8) . . . . ?
C30' C31' C32' C33' -177.9(5) . . . . ?
C30' C31' C36' C35' 179.6(5) . . . . ?
C31' C32' C33' C34' -2.8(9) . . . . ?
C32' C31' C36' C35' 0.6(8) . . . . ?
C32' C33' C34' C35' 2.8(10) . . . . ?
C33' C34' C35' C36' -1.0(9) . . . . ?
C34' C35' C36' C31' -0.7(9) . . . . ?
C36' C31' C32' C33' 1.1(8) . . . . ?
N1' C9' C10' C11' 171.6(6) . . . . ?
N1' C9' C10' C15' -12.4(6) . . . . ?
N1' C17' C18' C19' 1.8(9) . . . . ?
N1' C17' C18' N2' 177.6(5) . . . . ?
N2' C18' C19' C8' -152.2(5) . . . . ?
N2' C18' C19' C20' 84.8(6) . . . . ?
O1' C7' C8' C9' -17.7(8) . . . . ?
O1' C7' C8' C19' 104.5(6) . . . . ?
O4' C23' C24' C25' -142.8(6) . . . . ?
O4' C23' C24' C29' 33.5(9) . . . . ?
O5' C30' C31' C32' -20.9(9) . . . . ?
O5' C30' C31' C36' 160.1(6) . . . . ?

_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_glj-104
_database_code_depnum_ccdc_archive 'CCDC 2116271'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-10-18 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_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 0.0181 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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6890(9)
_cell_length_b                   5.8460(4)
_cell_length_c                   19.4233(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.761(7)
_cell_angle_gamma                90
_cell_volume                     1325.74(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1520
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.7260
_cell_measurement_theta_min      4.3070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4331
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.522
_diffrn_reflns_theta_min         4.325
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  32.00   1.00    1.20    --  -40.73  57.00 120.00   25
  2  ω    -64.00 -38.00   1.00    1.20    --  -40.73  57.00 120.00   26
  3  ω    -64.00  29.00   1.00    1.20    --  -40.73  38.00  30.00   93
  4  ω   -103.00 -17.00   1.00    1.20    --  -40.73 -38.00-150.00   86
  5  ω    114.00 169.00   1.00    2.00    --  107.58 125.00-180.00   55
  6  ω     82.00 169.00   1.00    2.00    --  107.58  30.00 -30.00   87
  7  ω     37.00  85.00   1.00    2.00    --  107.58 -95.00-180.00   48
  8  ω     26.00 104.00   1.00    2.00    --  107.58 -95.00 120.00   78
  9  ω     37.00 133.00   1.00    2.00    --  107.58 -45.00 150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1100038000
_diffrn_orient_matrix_UB_12      0.0543533000
_diffrn_orient_matrix_UB_13      0.0374711000
_diffrn_orient_matrix_UB_21      0.0724288000
_diffrn_orient_matrix_UB_22      0.0549907000
_diffrn_orient_matrix_UB_23      0.0663194000
_diffrn_orient_matrix_UB_31      0.0080147000
_diffrn_orient_matrix_UB_32      0.2518207000
_diffrn_orient_matrix_UB_33      -0.0225284000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2022
_reflns_number_total             2563
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.078
_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     199
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.070
_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)+(0.0906P)²+0.0681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1660
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8)
2.d Tetrahedral OH refined with riding coordinates:
 O3(H3)
;
_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 0.65004(17) 0.9122(3) 0.54281(10) 0.0375(5) Uani 1 1 d . . . . .
O2 O 0.76770(16) 0.6302(3) 0.56574(9) 0.0342(4) Uani 1 1 d . . . . .
O3 O 0.89288(17) 0.0337(3) 0.46108(11) 0.0431(5) Uani 1 1 d . . . . .
H3 H 0.909223 0.079593 0.500213 0.065 Uiso 1 1 calc R U . . .
O4 O 0.66626(15) -0.0407(3) 0.33056(9) 0.0314(4) Uani 1 1 d . . . . .
N1 N 0.49772(16) 0.5782(3) 0.38580(10) 0.0227(4) Uani 1 1 d . . . . .
N2 N 0.69193(17) 0.7211(3) 0.52755(10) 0.0267(4) Uani 1 1 d . . . . .
C1 C 0.47886(19) 0.3508(4) 0.28815(11) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.4847(2) 0.1870(4) 0.23654(12) 0.0263(5) Uani 1 1 d . . . . .
H2 H 0.528980 0.056045 0.243493 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4231(2) 0.2223(4) 0.17420(13) 0.0302(5) Uani 1 1 d . . . . .
H3A H 0.425739 0.112780 0.139595 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3582(2) 0.4179(4) 0.16302(12) 0.0284(5) Uani 1 1 d . . . . .
H4 H 0.321029 0.442704 0.120258 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3483(2) 0.5781(4) 0.21562(13) 0.0278(5) Uani 1 1 d . . . . .
H5 H 0.302834 0.707472 0.208929 0.033 Uiso 1 1 calc R U . . .
C6 C 0.40780(19) 0.5402(4) 0.27820(12) 0.0239(5) Uani 1 1 d . . . . .
C7 C 0.40473(19) 0.6816(4) 0.34232(12) 0.0260(5) Uani 1 1 d . . . . .
H7A H 0.419935 0.841451 0.333014 0.031 Uiso 1 1 calc R U . . .
H7B H 0.331545 0.668176 0.363488 0.031 Uiso 1 1 calc R U . . .
C8 C 0.55371(19) 0.6887(4) 0.43625(11) 0.0240(5) Uani 1 1 d . . . . .
H8 H 0.524787 0.827704 0.450899 0.029 Uiso 1 1 calc R U . . .
C9 C 0.65241(19) 0.6070(4) 0.46777(11) 0.0235(5) Uani 1 1 d . . . . .
C10 C 0.71495(19) 0.4015(4) 0.44152(11) 0.0232(5) Uani 1 1 d . . . . .
H10 H 0.698992 0.268899 0.470404 0.028 Uiso 1 1 calc R U . . .
C11 C 0.66816(18) 0.3538(4) 0.36604(11) 0.0215(5) Uani 1 1 d . . . . .
H11 H 0.695732 0.475847 0.336496 0.026 Uiso 1 1 calc R U . . .
C12 C 0.53653(18) 0.3551(4) 0.36014(11) 0.0214(5) Uani 1 1 d . . . . .
H12 H 0.506345 0.231345 0.388069 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7216(2) 0.1306(4) 0.34394(11) 0.0245(5) Uani 1 1 d . . . . .
C14 C 0.8502(2) 0.1382(4) 0.34347(13) 0.0300(5) Uani 1 1 d . . . . .
H14A H 0.873003 0.242171 0.307711 0.036 Uiso 1 1 calc R U . . .
H14B H 0.879066 -0.012767 0.332986 0.036 Uiso 1 1 calc R U . . .
C15 C 0.9026(2) 0.2175(4) 0.41334(14) 0.0307(5) Uani 1 1 d . . . . .
H15 H 0.984100 0.249241 0.408244 0.037 Uiso 1 1 calc R U . . .
C16 C 0.8461(2) 0.4328(4) 0.43903(13) 0.0292(5) Uani 1 1 d . . . . .
H16A H 0.862298 0.559425 0.408729 0.035 Uiso 1 1 calc R U . . .
H16B H 0.877708 0.469670 0.484778 0.035 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 N2 1.260(3) . ?
O2 N2 1.247(3) . ?
O3 H3 0.8200 . ?
O3 C15 1.427(3) . ?
O4 C13 1.214(3) . ?
N1 C7 1.474(3) . ?
N1 C8 1.321(3) . ?
N1 C12 1.476(3) . ?
N2 C9 1.398(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.392(3) . ?
C1 C12 1.523(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 C7 1.497(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C9 1.366(3) . ?
C9 C10 1.508(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.565(3) . ?
C10 C16 1.547(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.537(3) . ?
C11 C13 1.518(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.504(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.534(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.518(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 O3 H3 109.5 . . ?
C7 N1 C12 113.53(18) . . ?
C8 N1 C7 123.4(2) . . ?
C8 N1 C12 122.25(18) . . ?
O1 N2 C9 120.1(2) . . ?
O2 N2 O1 120.7(2) . . ?
O2 N2 C9 119.2(2) . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 C12 129.7(2) . . ?
C6 C1 C12 110.43(19) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C7 111.2(2) . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 C7 127.5(2) . . ?
N1 C7 C6 101.76(18) . . ?
N1 C7 H7A 111.4 . . ?
N1 C7 H7B 111.4 . . ?
C6 C7 H7A 111.4 . . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
N1 C8 H8 118.7 . . ?
N1 C8 C9 122.6(2) . . ?
C9 C8 H8 118.7 . . ?
N2 C9 C10 121.0(2) . . ?
C8 C9 N2 116.3(2) . . ?
C8 C9 C10 122.7(2) . . ?
C9 C10 H10 109.1 . . ?
C9 C10 C11 107.79(18) . . ?
C9 C10 C16 114.42(19) . . ?
C11 C10 H10 109.1 . . ?
C16 C10 H10 109.1 . . ?
C16 C10 C11 107.10(18) . . ?
C10 C11 H11 108.0 . . ?
C12 C11 C10 111.86(17) . . ?
C12 C11 H11 108.0 . . ?
C13 C11 C10 106.74(18) . . ?
C13 C11 H11 108.0 . . ?
C13 C11 C12 114.05(19) . . ?
N1 C12 C1 101.25(17) . . ?
N1 C12 C11 107.58(17) . . ?
N1 C12 H12 109.9 . . ?
C1 C12 C11 117.74(18) . . ?
C1 C12 H12 109.9 . . ?
C11 C12 H12 109.9 . . ?
O4 C13 C11 123.2(2) . . ?
O4 C13 C14 123.1(2) . . ?
C14 C13 C11 113.7(2) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C13 C14 C15 111.1(2) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
O3 C15 C14 107.8(2) . . ?
O3 C15 H15 108.5 . . ?
O3 C15 C16 111.2(2) . . ?
C14 C15 H15 108.5 . . ?
C16 C15 C14 112.3(2) . . ?
C16 C15 H15 108.5 . . ?
C10 C16 H16A 109.4 . . ?
C10 C16 H16B 109.4 . . ?
C15 C16 C10 111.1(2) . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C9 C8 -12.8(3) . . . . ?
O1 N2 C9 C10 168.7(2) . . . . ?
O2 N2 C9 C8 166.3(2) . . . . ?
O2 N2 C9 C10 -12.2(3) . . . . ?
O3 C15 C16 C10 -66.3(3) . . . . ?
O4 C13 C14 C15 -123.2(2) . . . . ?
N1 C8 C9 N2 -169.6(2) . . . . ?
N1 C8 C9 C10 8.8(3) . . . . ?
N2 C9 C10 C11 -166.07(19) . . . . ?
N2 C9 C10 C16 -47.1(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C6 C7 N1 10.2(2) . . . . ?
C2 C1 C6 C5 -4.6(3) . . . . ?
C2 C1 C6 C7 174.0(2) . . . . ?
C2 C1 C12 N1 177.9(2) . . . . ?
C2 C1 C12 C11 61.0(3) . . . . ?
C2 C3 C4 C5 -3.5(4) . . . . ?
C3 C4 C5 C6 2.1(3) . . . . ?
C4 C5 C6 C1 2.0(3) . . . . ?
C4 C5 C6 C7 -176.5(2) . . . . ?
C5 C6 C7 N1 -171.2(2) . . . . ?
C6 C1 C2 C3 3.2(3) . . . . ?
C6 C1 C12 N1 -5.1(2) . . . . ?
C6 C1 C12 C11 -122.0(2) . . . . ?
C7 N1 C8 C9 -167.8(2) . . . . ?
C7 N1 C12 C1 12.2(2) . . . . ?
C7 N1 C12 C11 136.32(19) . . . . ?
C8 N1 C7 C6 155.6(2) . . . . ?
C8 N1 C12 C1 -157.6(2) . . . . ?
C8 N1 C12 C11 -33.5(3) . . . . ?
C8 C9 C10 C11 15.6(3) . . . . ?
C8 C9 C10 C16 134.6(2) . . . . ?
C9 C10 C11 C12 -47.9(2) . . . . ?
C9 C10 C11 C13 -173.32(17) . . . . ?
C9 C10 C16 C15 178.97(19) . . . . ?
C10 C11 C12 N1 56.6(2) . . . . ?
C10 C11 C12 C1 170.03(18) . . . . ?
C10 C11 C13 O4 115.8(2) . . . . ?
C10 C11 C13 C14 -61.4(2) . . . . ?
C11 C10 C16 C15 -61.6(2) . . . . ?
C11 C13 C14 C15 54.0(3) . . . . ?
C12 N1 C7 C6 -14.1(2) . . . . ?
C12 N1 C8 C9 1.0(3) . . . . ?
C12 C1 C2 C3 179.9(2) . . . . ?
C12 C1 C6 C5 178.0(2) . . . . ?
C12 C1 C6 C7 -3.3(3) . . . . ?
C12 C11 C13 O4 -8.3(3) . . . . ?
C12 C11 C13 C14 174.52(19) . . . . ?
C13 C11 C12 N1 177.85(17) . . . . ?
C13 C11 C12 C1 -68.7(2) . . . . ?
C13 C14 C15 O3 73.8(2) . . . . ?
C13 C14 C15 C16 -49.1(3) . . . . ?
C14 C15 C16 C10 54.7(3) . . . . ?
C16 C10 C11 C12 -171.49(18) . . . . ?
C16 C10 C11 C13 63.1(2) . . . . ?

_olex2_date_sample_data_collection 2021-10-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.648
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2071228'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2019-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N3 O5'
_chemical_formula_sum            'C27 H23 N3 O5'
_chemical_formula_weight         469.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.719(3)
_cell_length_b                   11.529(5)
_cell_length_c                   12.887(5)
_cell_angle_alpha                86.887(13)
_cell_angle_beta                 72.756(13)
_cell_angle_gamma                74.684(12)
_cell_volume                     1192.8(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.22
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1117 before and 0.0660 after correction. The Ratio of minimum to maximum transmission is 0.7983. 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    1.307
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.0888
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16372
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         2.437
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2473
_reflns_number_total             4927
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4927
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.021
_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)+(0.0856P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1937
_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, All O(H) groups
2. Restrained distances
 C24-C23
 1.55 with sigma of 0.02
 C26-C27
 1.55 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C27(H27A,H27B,H27C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2877(5) 0.0480(3) 0.9882(3) 0.0801(12) Uani 1 1 d . . . . .
H1 H 0.3870 -0.0085 0.9560 0.096 Uiso 1 1 calc R . . . .
C2 C 0.2260(6) 0.0569(4) 1.0994(3) 0.1094(17) Uani 1 1 d . . . . .
H2 H 0.2841 0.0068 1.1418 0.131 Uiso 1 1 calc R . . . .
C3 C 0.0808(5) 0.1383(4) 1.1478(3) 0.0976(14) Uani 1 1 d . . . . .
H3 H 0.0408 0.1447 1.2232 0.117 Uiso 1 1 calc R . . . .
C4 C -0.0067(5) 0.2108(4) 1.0863(3) 0.0782(11) Uani 1 1 d . . . . .
H4 H -0.1074 0.2652 1.1199 0.094 Uiso 1 1 calc R . . . .
C5 C 0.0539(4) 0.2036(3) 0.9742(2) 0.0605(9) Uani 1 1 d . . . . .
H5 H -0.0058 0.2535 0.9325 0.073 Uiso 1 1 calc R . . . .
C6 C 0.2038(4) 0.1220(3) 0.9237(2) 0.0486(7) Uani 1 1 d . . . . .
C7 C 0.2860(4) 0.1112(2) 0.8047(2) 0.0451(7) Uani 1 1 d . . . . .
C8 C 0.2045(3) 0.1897(2) 0.7234(2) 0.0412(7) Uani 1 1 d . . . . .
C9 C 0.3028(3) 0.1405(2) 0.60566(19) 0.0390(6) Uani 1 1 d . . . . .
H9 H 0.4217 0.1320 0.5937 0.047 Uiso 1 1 calc R . . . .
C10 C 0.2783(3) 0.0240(2) 0.5711(2) 0.0427(7) Uani 1 1 d . . . . .
C11 C 0.2886(4) -0.0858(2) 0.6233(2) 0.0553(8) Uani 1 1 d . . . . .
H11 H 0.3149 -0.0966 0.6886 0.066 Uiso 1 1 calc R . . . .
C12 C 0.2581(4) -0.1787(3) 0.5741(3) 0.0636(9) Uani 1 1 d . . . . .
H12 H 0.2620 -0.2522 0.6082 0.076 Uiso 1 1 calc R . . . .
C13 C 0.2223(4) -0.1645(3) 0.4764(3) 0.0612(9) Uani 1 1 d . . . . .
H13 H 0.2030 -0.2281 0.4450 0.073 Uiso 1 1 calc R . . . .
C14 C 0.2151(4) -0.0568(3) 0.4252(2) 0.0552(8) Uani 1 1 d . . . . .
H14 H 0.1928 -0.0471 0.3586 0.066 Uiso 1 1 calc R . . . .
C15 C 0.2411(3) 0.0368(2) 0.4733(2) 0.0448(7) Uani 1 1 d . . . . .
C16 C 0.2347(4) 0.1609(2) 0.4327(2) 0.0499(8) Uani 1 1 d . . . . .
H16A H 0.3278 0.1616 0.3690 0.060 Uiso 1 1 calc R . . . .
H16B H 0.1316 0.1966 0.4153 0.060 Uiso 1 1 calc R . . . .
C17 C 0.1848(4) 0.3412(2) 0.5463(2) 0.0465(7) Uani 1 1 d . . . . .
H17 H 0.1506 0.3900 0.4931 0.056 Uiso 1 1 calc R . . . .
C18 C 0.1718(4) 0.3926(2) 0.6416(2) 0.0471(7) Uani 1 1 d . . . . .
C19 C 0.2118(3) 0.3232(2) 0.7361(2) 0.0438(7) Uani 1 1 d . . . . .
H19 H 0.1246 0.3586 0.8022 0.053 Uiso 1 1 calc R . . . .
C20 C 0.3750(3) 0.3321(2) 0.7471(2) 0.0476(7) Uani 1 1 d . . . . .
H20 H 0.4719 0.2949 0.6939 0.057 Uiso 1 1 calc R . . . .
C21 C 0.3884(4) 0.3895(3) 0.8276(3) 0.0554(8) Uani 1 1 d . . . . .
H21 H 0.2957 0.4112 0.8881 0.067 Uiso 1 1 calc R . . . .
C22 C 0.0303(4) 0.1861(2) 0.7425(2) 0.0430(7) Uani 1 1 d . . . . .
C23 C 0.5506(7) 0.3005(4) 0.9936(4) 0.1171(18) Uani 1 1 d D . . . .
H23A H 0.4336 0.3338 1.0262 0.176 Uiso 1 1 calc GR . . . .
H23B H 0.6067 0.2897 1.0486 0.176 Uiso 1 1 calc GR . . . .
H23C H 0.5687 0.2242 0.9593 0.176 Uiso 1 1 calc GR . . . .
C24 C 0.6163(6) 0.3829(4) 0.9119(4) 0.0952(15) Uani 1 1 d D . . . .
C25 C 0.5436(4) 0.4229(3) 0.8290(3) 0.0719(10) Uani 1 1 d . . . . .
C26 C 0.6099(5) 0.4990(4) 0.7490(4) 0.0900(13) Uani 1 1 d D . . . .
C27 C 0.5344(8) 0.5538(6) 0.6633(5) 0.146(2) Uani 1 1 d D . . . .
H27A H 0.5943 0.5103 0.5958 0.218 Uiso 1 1 calc GR . . . .
H27B H 0.5395 0.6361 0.6553 0.218 Uiso 1 1 calc GR . . . .
H27C H 0.4204 0.5507 0.6833 0.218 Uiso 1 1 calc GR . . . .
N1 N 0.2445(3) 0.22363(19) 0.52614(17) 0.0444(6) Uani 1 1 d . . . . .
N2 N 0.1153(3) 0.5189(2) 0.6527(2) 0.0605(7) Uani 1 1 d . . . . .
N3 N -0.1028(3) 0.1840(2) 0.7524(2) 0.0627(7) Uani 1 1 d . . . . .
O1 O 0.4234(3) 0.04468(19) 0.76728(16) 0.0642(7) Uani 1 1 d . . . . .
O2 O 0.0905(3) 0.56568(19) 0.7420(2) 0.0755(7) Uani 1 1 d . . . . .
O3 O 0.0951(3) 0.57994(19) 0.5726(2) 0.0811(8) Uani 1 1 d . . . . .
O4 O 0.7429(4) 0.4167(3) 0.9163(3) 0.1329(15) Uani 1 1 d . . . . .
O5 O 0.7423(4) 0.5302(4) 0.7513(4) 0.1398(14) Uani 1 1 d . . . . .
H5A H 0.7826 0.4899 0.7958 0.210 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.372(5) . ?
C1 C6 1.381(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.363(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(4) . ?
C6 C7 1.485(4) . ?
C7 C8 1.556(4) . ?
C7 O1 1.211(3) . ?
C8 C9 1.557(4) . ?
C8 C19 1.576(4) . ?
C8 C22 1.477(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.523(4) . ?
C9 N1 1.474(3) . ?
C10 C11 1.395(4) . ?
C10 C15 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(4) . ?
C15 C16 1.489(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 N1 1.473(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.354(4) . ?
C17 N1 1.327(3) . ?
C18 C19 1.497(4) . ?
C18 N2 1.409(3) . ?
C19 H19 0.9800 . ?
C19 C20 1.502(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.309(4) . ?
C21 H21 0.9300 . ?
C21 C25 1.507(5) . ?
C22 N3 1.136(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 C24 1.470(6) . ?
C24 C25 1.395(5) . ?
C24 O4 1.281(5) . ?
C25 C26 1.407(6) . ?
C26 C27 1.479(6) . ?
C26 O5 1.305(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N2 O2 1.233(3) . ?
N2 O3 1.248(3) . ?
O5 H5A 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
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.7(3) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 C7 116.7(3) . . ?
C5 C6 C7 124.9(3) . . ?
C6 C7 C8 121.6(2) . . ?
O1 C7 C6 121.1(3) . . ?
O1 C7 C8 117.2(2) . . ?
C7 C8 C9 109.0(2) . . ?
C7 C8 C19 108.3(2) . . ?
C9 C8 C19 110.2(2) . . ?
C22 C8 C7 112.1(2) . . ?
C22 C8 C9 107.5(2) . . ?
C22 C8 C19 109.8(2) . . ?
C8 C9 H9 109.5 . . ?
C10 C9 C8 117.4(2) . . ?
C10 C9 H9 109.5 . . ?
N1 C9 C8 110.1(2) . . ?
N1 C9 H9 109.5 . . ?
N1 C9 C10 100.6(2) . . ?
C11 C10 C9 129.4(3) . . ?
C15 C10 C9 110.8(2) . . ?
C15 C10 C11 119.8(3) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 C10 117.7(3) . . ?
C12 C11 H11 121.1 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C16 110.9(2) . . ?
C14 C15 C10 121.5(3) . . ?
C14 C15 C16 127.7(3) . . ?
C15 C16 H16A 111.3 . . ?
C15 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?
N1 C16 C15 102.2(2) . . ?
N1 C16 H16A 111.3 . . ?
N1 C16 H16B 111.3 . . ?
C18 C17 H17 118.9 . . ?
N1 C17 H17 118.9 . . ?
N1 C17 C18 122.3(3) . . ?
C17 C18 C19 124.0(2) . . ?
C17 C18 N2 117.9(3) . . ?
N2 C18 C19 118.2(3) . . ?
C8 C19 H19 107.8 . . ?
C18 C19 C8 108.5(2) . . ?
C18 C19 H19 107.8 . . ?
C18 C19 C20 111.5(2) . . ?
C20 C19 C8 113.3(2) . . ?
C20 C19 H19 107.8 . . ?
C19 C20 H20 118.2 . . ?
C21 C20 C19 123.6(3) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 H21 117.7 . . ?
C20 C21 C25 124.5(3) . . ?
C25 C21 H21 117.7 . . ?
N3 C22 C8 177.0(3) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
C25 C24 C23 120.7(4) . . ?
O4 C24 C23 119.4(4) . . ?
O4 C24 C25 119.9(5) . . ?
C24 C25 C21 120.0(4) . . ?
C24 C25 C26 120.5(4) . . ?
C26 C25 C21 119.4(3) . . ?
C25 C26 C27 124.5(4) . . ?
O5 C26 C25 119.6(4) . . ?
O5 C26 C27 115.7(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C16 N1 C9 112.9(2) . . ?
C17 N1 C9 122.2(2) . . ?
C17 N1 C16 124.2(2) . . ?
O2 N2 C18 118.3(3) . . ?
O2 N2 O3 122.0(3) . . ?
O3 N2 C18 119.7(3) . . ?
C26 O5 H5A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17 O3 0.93 2.47 3.165(4) 132.1 2_566
O5 H5A O4 0.82 1.71 2.436(6) 145.8 .

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
C1 C2 C3 C4 1.1(8) . . . . ?
C1 C6 C7 C8 -179.8(3) . . . . ?
C1 C6 C7 O1 -3.4(5) . . . . ?
C2 C1 C6 C5 -1.4(6) . . . . ?
C2 C1 C6 C7 176.0(4) . . . . ?
C2 C3 C4 C5 -1.4(7) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C5 C6 C7 -176.1(3) . . . . ?
C5 C6 C7 C8 -2.7(5) . . . . ?
C5 C6 C7 O1 173.8(3) . . . . ?
C6 C1 C2 C3 0.3(8) . . . . ?
C6 C7 C8 C9 -169.1(2) . . . . ?
C6 C7 C8 C19 71.0(3) . . . . ?
C6 C7 C8 C22 -50.2(3) . . . . ?
C7 C8 C9 C10 74.4(3) . . . . ?
C7 C8 C9 N1 -171.5(2) . . . . ?
C7 C8 C19 C18 166.7(2) . . . . ?
C7 C8 C19 C20 42.3(3) . . . . ?
C8 C9 C10 C11 -50.8(4) . . . . ?
C8 C9 C10 C15 129.3(2) . . . . ?
C8 C9 N1 C16 -140.8(2) . . . . ?
C8 C9 N1 C17 30.0(3) . . . . ?
C8 C19 C20 C21 -125.6(3) . . . . ?
C9 C8 C19 C18 47.5(3) . . . . ?
C9 C8 C19 C20 -76.9(3) . . . . ?
C9 C10 C11 C12 179.2(3) . . . . ?
C9 C10 C15 C14 179.4(3) . . . . ?
C9 C10 C15 C16 -0.7(3) . . . . ?
C10 C9 N1 C16 -16.3(3) . . . . ?
C10 C9 N1 C17 154.5(2) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C10 C15 C16 N1 -9.0(3) . . . . ?
C11 C10 C15 C14 -0.5(4) . . . . ?
C11 C10 C15 C16 179.4(2) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C13 C14 C15 C10 1.5(4) . . . . ?
C13 C14 C15 C16 -178.4(3) . . . . ?
C14 C15 C16 N1 170.9(3) . . . . ?
C15 C10 C11 C12 -0.9(4) . . . . ?
C15 C16 N1 C9 16.2(3) . . . . ?
C15 C16 N1 C17 -154.4(2) . . . . ?
C17 C18 C19 C8 -20.6(4) . . . . ?
C17 C18 C19 C20 104.9(3) . . . . ?
C17 C18 N2 O2 174.3(3) . . . . ?
C17 C18 N2 O3 -7.1(4) . . . . ?
C18 C17 N1 C9 -0.7(4) . . . . ?
C18 C17 N1 C16 169.0(3) . . . . ?
C18 C19 C20 C21 111.7(3) . . . . ?
C19 C8 C9 C10 -166.9(2) . . . . ?
C19 C8 C9 N1 -52.7(3) . . . . ?
C19 C18 N2 O2 -5.0(4) . . . . ?
C19 C18 N2 O3 173.7(3) . . . . ?
C19 C20 C21 C25 -166.2(3) . . . . ?
C20 C21 C25 C24 -122.4(4) . . . . ?
C20 C21 C25 C26 60.4(5) . . . . ?
C21 C25 C26 C27 2.2(6) . . . . ?
C21 C25 C26 O5 178.5(3) . . . . ?
C22 C8 C9 C10 -47.3(3) . . . . ?
C22 C8 C9 N1 66.9(3) . . . . ?
C22 C8 C19 C18 -70.7(3) . . . . ?
C22 C8 C19 C20 164.9(2) . . . . ?
C23 C24 C25 C21 4.7(5) . . . . ?
C23 C24 C25 C26 -178.1(4) . . . . ?
C24 C25 C26 C27 -174.9(4) . . . . ?
C24 C25 C26 O5 1.3(6) . . . . ?
N1 C9 C10 C11 -170.1(3) . . . . ?
N1 C9 C10 C15 10.0(3) . . . . ?
N1 C17 C18 C19 -4.2(5) . . . . ?
N1 C17 C18 N2 176.6(3) . . . . ?
N2 C18 C19 C8 158.6(2) . . . . ?
N2 C18 C19 C20 -75.9(3) . . . . ?
O1 C7 C8 C9 14.3(4) . . . . ?
O1 C7 C8 C19 -105.6(3) . . . . ?
O1 C7 C8 C22 133.2(3) . . . . ?
O4 C24 C25 C21 -176.2(3) . . . . ?
O4 C24 C25 C26 1.0(5) . . . . ?


_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_hd_wql33
_database_code_depnum_ccdc_archive 'CCDC 2086413'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H23 F N2 O5'
_chemical_formula_sum            'C25 H23 F N2 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         450.45

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   5.98830(10)
_cell_length_b                   22.0176(5)
_cell_length_c                   16.5031(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.3100(10)
_cell_angle_gamma                90
_cell_volume                     2166.56(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9803
_cell_measurement_theta_min      2.6890
_cell_measurement_theta_max      72.4123
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            24084
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         72.43
_diffrn_reflns_theta_full        72.43
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             4294
_reflns_number_gt                3737
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1362
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         4294
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0751P)²+0.8196P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0028(4)

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.80594(17) 0.52158(6) 0.10900(6) 0.0346(3) Uani d . . . 1 . .
O O1 0.73516(19) 0.85827(5) 0.41638(7) 0.0252(3) Uani d . . . 1 . .
O O2 0.9859(2) 0.79244(6) 0.47693(8) 0.0290(3) Uani d . . . 1 . .
O O3 -0.02811(18) 0.63977(6) 0.36829(8) 0.0256(3) Uani d . . . 1 . .
O O4 0.5630(2) 0.58590(6) 0.62521(7) 0.0269(3) Uani d . . . 1 . .
O O5 0.8514(2) 0.53918(6) 0.58384(7) 0.0271(3) Uani d . . . 1 . .
N N1 0.6018(2) 0.54737(6) 0.35241(8) 0.0186(3) Uani d . . . 1 . .
N N2 0.6709(2) 0.56763(6) 0.56886(8) 0.0206(3) Uani d . . . 1 . .
C C1 0.8101(3) 0.93517(9) 0.32267(11) 0.0305(4) Uani d . . . 1 . .
H H23 0.729973 0.91083 0.279561 0.046 Uiso calc U . R 1 . .
H H3 0.927314 0.959032 0.299762 0.046 Uiso calc U . R 1 . .
H H1 0.704531 0.9626 0.34615 0.046 Uiso calc U . R 1 . .
C C2 0.9153(3) 0.89382(8) 0.38787(11) 0.0273(4) Uani d . . . 1 . .
H H22 1.027279 0.866968 0.365556 0.033 Uiso calc U . R 1 . .
H H21 0.991347 0.917841 0.433057 0.033 Uiso calc U . R 1 . .
C C3 0.7941(3) 0.80759(7) 0.45961(10) 0.0214(3) Uani d . . . 1 . .
C C4 0.5916(3) 0.77458(8) 0.47814(10) 0.0222(3) Uani d . . . 1 . .
H H4 0.450812 0.794735 0.471753 0.027 Uiso calc U . R 1 . .
C C5 0.6003(3) 0.71736(8) 0.50354(10) 0.0208(3) Uani d . . . 1 . .
H H5 0.743209 0.698695 0.513414 0.025 Uiso calc U . R 1 . .
C C6 0.3971(3) 0.68070(7) 0.51746(10) 0.0210(3) Uani d . . . 1 . .
H H7 0.261276 0.705018 0.501214 0.025 Uiso calc U . R 1 . .
H H6 0.398441 0.671681 0.576275 0.025 Uiso calc U . R 1 . .
C C7 0.3845(2) 0.62023(7) 0.46932(9) 0.0185(3) Uani d . . . 1 . .
H H20 0.245144 0.598183 0.481094 0.022 Uiso calc U . R 1 . .
C C8 0.3688(2) 0.63557(7) 0.37703(9) 0.0170(3) Uani d . . . 1 . .
H H13 0.492685 0.663991 0.366073 0.02 Uiso calc U . R 1 . .
C C9 0.3870(2) 0.57710(7) 0.32668(9) 0.0178(3) Uani d . . . 1 . .
H H12 0.261041 0.549149 0.336953 0.021 Uiso calc U . R 1 . .
C C10 0.3998(3) 0.58315(7) 0.23612(10) 0.0201(3) Uani d . . . 1 . .
C C11 0.2483(3) 0.61055(8) 0.17821(11) 0.0249(4) Uani d . . . 1 . .
H H11 0.117153 0.629898 0.193866 0.03 Uiso calc U . R 1 . .
C C12 0.2929(3) 0.60900(8) 0.09685(11) 0.0301(4) Uani d . . . 1 . .
H H8 0.192809 0.628436 0.056962 0.036 Uiso calc U . R 1 . .
C C13 0.4809(3) 0.57957(9) 0.07316(11) 0.0293(4) Uani d . . . 1 . .
H H2 0.509848 0.578608 0.017536 0.035 Uiso calc U . R 1 . .
C C14 0.5836(2) 0.57840(7) 0.48822(9) 0.0187(3) Uani d . . . 1 . .
C C15 0.6870(2) 0.54810(7) 0.42923(10) 0.0185(3) Uani d . . . 1 . .
H H19 0.823244 0.527102 0.444031 0.022 Uiso calc U . R 1 . .
C C16 0.6254(3) 0.55168(8) 0.13179(11) 0.0246(4) Uani d . . . 1 . .
C C17 0.5886(3) 0.55340(7) 0.21322(10) 0.0212(3) Uani d . . . 1 . .
C C18 0.7182(3) 0.52339(8) 0.28492(10) 0.0216(3) Uani d . . . 1 . .
H H9 0.707323 0.478581 0.281615 0.026 Uiso calc U . R 1 . .
H H10 0.878033 0.535537 0.289622 0.026 Uiso calc U . R 1 . .
C C19 0.1419(2) 0.66540(7) 0.35106(9) 0.0186(3) Uani d . . . 1 . .
C C20 0.1251(3) 0.72164(7) 0.30036(9) 0.0192(3) Uani d . . . 1 . .
C C21 -0.0838(3) 0.73538(8) 0.25923(10) 0.0244(4) Uani d . . . 1 . .
H H14 -0.208385 0.709632 0.265349 0.029 Uiso calc U . R 1 . .
C C22 -0.1105(3) 0.78619(9) 0.20965(11) 0.0286(4) Uani d . . . 1 . .
H H15 -0.25232 0.794694 0.181223 0.034 Uiso calc U . R 1 . .
C C23 0.0698(3) 0.82465(8) 0.20153(11) 0.0278(4) Uani d . . . 1 . .
H H16 0.051018 0.859673 0.16796 0.033 Uiso calc U . R 1 . .
C C24 0.2773(3) 0.81191(8) 0.24247(10) 0.0246(4) Uani d . . . 1 . .
H H18 0.400306 0.838446 0.237376 0.03 Uiso calc U . R 1 . .
C C25 0.3055(3) 0.76019(7) 0.29110(10) 0.0203(3) Uani d . . . 1 . .
H H17 0.448662 0.751173 0.318104 0.024 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C16 . 1.351(2) ?
O1 C3 . 1.353(2) ?
O1 C2 . 1.447(2) ?
O2 C3 . 1.205(2) ?
O3 C19 . 1.220(2) ?
O4 N2 . 1.2472(19) ?
O5 N2 . 1.2539(18) ?
N1 C15 . 1.322(2) ?
N1 C18 . 1.466(2) ?
N1 C9 . 1.4706(19) ?
N2 C14 . 1.404(2) ?
C1 C2 . 1.503(2) ?
C1 H23 . 0.98 ?
C1 H3 . 0.98 ?
C1 H1 . 0.98 ?
C2 H22 . 0.99 ?
C2 H21 . 0.99 ?
C3 C4 . 1.470(2) ?
C4 C5 . 1.327(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.495(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.549(2) ?
C6 H7 . 0.99 ?
C6 H6 . 0.99 ?
C7 C14 . 1.516(2) ?
C7 C8 . 1.554(2) ?
C7 H20 . 1.0 ?
C8 C19 . 1.534(2) ?
C8 C9 . 1.542(2) ?
C8 H13 . 1.0 ?
C9 C10 . 1.509(2) ?
C9 H12 . 1.0 ?
C10 C17 . 1.389(2) ?
C10 C11 . 1.393(2) ?
C11 C12 . 1.393(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.386(3) ?
C12 H8 . 0.95 ?
C13 C16 . 1.381(2) ?
C13 H2 . 0.95 ?
C14 C15 . 1.374(2) ?
C15 H19 . 0.95 ?
C16 C17 . 1.382(2) ?
C17 C18 . 1.506(2) ?
C18 H9 . 0.99 ?
C18 H10 . 0.99 ?
C19 C20 . 1.493(2) ?
C20 C25 . 1.393(2) ?
C20 C21 . 1.400(2) ?
C21 C22 . 1.387(3) ?
C21 H14 . 0.95 ?
C22 C23 . 1.388(3) ?
C22 H15 . 0.95 ?
C23 C24 . 1.387(2) ?
C23 H16 . 0.95 ?
C24 C25 . 1.394(2) ?
C24 H18 . 0.95 ?
C25 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C2 . . 116.84(13) ?
C15 N1 C18 . . 124.38(13) ?
C15 N1 C9 . . 121.40(13) ?
C18 N1 C9 . . 113.93(12) ?
O4 N2 O5 . . 120.72(13) ?
O4 N2 C14 . . 118.63(13) ?
O5 N2 C14 . . 120.64(14) ?
C2 C1 H23 . . 109.5 ?
C2 C1 H3 . . 109.5 ?
H23 C1 H3 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H23 C1 H1 . . 109.5 ?
H3 C1 H1 . . 109.5 ?
O1 C2 C1 . . 106.55(14) ?
O1 C2 H22 . . 110.4 ?
C1 C2 H22 . . 110.4 ?
O1 C2 H21 . . 110.4 ?
C1 C2 H21 . . 110.4 ?
H22 C2 H21 . . 108.6 ?
O2 C3 O1 . . 123.35(16) ?
O2 C3 C4 . . 126.90(15) ?
O1 C3 C4 . . 109.71(13) ?
C5 C4 C3 . . 121.75(15) ?
C5 C4 H4 . . 119.1 ?
C3 C4 H4 . . 119.1 ?
C4 C5 C6 . . 123.54(15) ?
C4 C5 H5 . . 118.2 ?
C6 C5 H5 . . 118.2 ?
C5 C6 C7 . . 112.77(13) ?
C5 C6 H7 . . 109.0 ?
C7 C6 H7 . . 109.0 ?
C5 C6 H6 . . 109.0 ?
C7 C6 H6 . . 109.0 ?
H7 C6 H6 . . 107.8 ?
C14 C7 C6 . . 114.62(12) ?
C14 C7 C8 . . 107.98(12) ?
C6 C7 C8 . . 108.16(12) ?
C14 C7 H20 . . 108.6 ?
C6 C7 H20 . . 108.6 ?
C8 C7 H20 . . 108.6 ?
C19 C8 C9 . . 108.18(12) ?
C19 C8 C7 . . 109.80(12) ?
C9 C8 C7 . . 110.24(12) ?
C19 C8 H13 . . 109.5 ?
C9 C8 H13 . . 109.5 ?
C7 C8 H13 . . 109.5 ?
N1 C9 C10 . . 101.65(12) ?
N1 C9 C8 . . 108.65(11) ?
C10 C9 C8 . . 118.21(13) ?
N1 C9 H12 . . 109.3 ?
C10 C9 H12 . . 109.3 ?
C8 C9 H12 . . 109.3 ?
C17 C10 C11 . . 120.82(15) ?
C17 C10 C9 . . 110.18(13) ?
C11 C10 C9 . . 128.91(15) ?
C10 C11 C12 . . 118.68(16) ?
C10 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
C13 C12 C11 . . 121.08(16) ?
C13 C12 H8 . . 119.5 ?
C11 C12 H8 . . 119.5 ?
C16 C13 C12 . . 118.86(17) ?
C16 C13 H2 . . 120.6 ?
C12 C13 H2 . . 120.6 ?
C15 C14 N2 . . 115.93(14) ?
C15 C14 C7 . . 123.13(14) ?
N2 C14 C7 . . 120.93(14) ?
N1 C15 C14 . . 121.76(14) ?
N1 C15 H19 . . 119.1 ?
C14 C15 H19 . . 119.1 ?
F1 C16 C13 . . 119.26(16) ?
F1 C16 C17 . . 119.20(15) ?
C13 C16 C17 . . 121.54(16) ?
C16 C17 C10 . . 118.98(15) ?
C16 C17 C18 . . 129.40(15) ?
C10 C17 C18 . . 111.48(14) ?
N1 C18 C17 . . 101.09(12) ?
N1 C18 H9 . . 111.6 ?
C17 C18 H9 . . 111.6 ?
N1 C18 H10 . . 111.6 ?
C17 C18 H10 . . 111.6 ?
H9 C18 H10 . . 109.4 ?
O3 C19 C20 . . 119.98(14) ?
O3 C19 C8 . . 118.25(14) ?
C20 C19 C8 . . 121.60(13) ?
C25 C20 C21 . . 118.83(15) ?
C25 C20 C19 . . 123.66(14) ?
C21 C20 C19 . . 117.50(14) ?
C22 C21 C20 . . 120.64(16) ?
C22 C21 H14 . . 119.7 ?
C20 C21 H14 . . 119.7 ?
C21 C22 C23 . . 120.05(15) ?
C21 C22 H15 . . 120.0 ?
C23 C22 H15 . . 120.0 ?
C24 C23 C22 . . 119.95(16) ?
C24 C23 H16 . . 120.0 ?
C22 C23 H16 . . 120.0 ?
C23 C24 C25 . . 120.05(16) ?
C23 C24 H18 . . 120.0 ?
C25 C24 H18 . . 120.0 ?
C20 C25 C24 . . 120.46(14) ?
C20 C25 H17 . . 119.8 ?
C24 C25 H17 . . 119.8 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 O1 C2 C1 . . . . 163.46(15) ?
C2 O1 C3 O2 . . . . 2.3(2) ?
C2 O1 C3 C4 . . . . -175.58(14) ?
O2 C3 C4 C5 . . . . -13.1(3) ?
O1 C3 C4 C5 . . . . 164.70(15) ?
C3 C4 C5 C6 . . . . -175.54(14) ?
C4 C5 C6 C7 . . . . 125.06(17) ?
C5 C6 C7 C14 . . . . 58.56(17) ?
C5 C6 C7 C8 . . . . -61.95(16) ?
C14 C7 C8 C19 . . . . 167.12(12) ?
C6 C7 C8 C19 . . . . -68.31(15) ?
C14 C7 C8 C9 . . . . 48.02(15) ?
C6 C7 C8 C9 . . . . 172.60(11) ?
C15 N1 C9 C10 . . . . 161.49(14) ?
C18 N1 C9 C10 . . . . -12.57(16) ?
C15 N1 C9 C8 . . . . 36.12(19) ?
C18 N1 C9 C8 . . . . -137.94(13) ?
C19 C8 C9 N1 . . . . -178.73(12) ?
C7 C8 C9 N1 . . . . -58.66(15) ?
C19 C8 C9 C10 . . . . 66.25(16) ?
C7 C8 C9 C10 . . . . -173.68(12) ?
N1 C9 C10 C17 . . . . 6.51(16) ?
C8 C9 C10 C17 . . . . 125.27(14) ?
N1 C9 C10 C11 . . . . -176.82(16) ?
C8 C9 C10 C11 . . . . -58.1(2) ?
C17 C10 C11 C12 . . . . -1.8(2) ?
C9 C10 C11 C12 . . . . -178.11(16) ?
C10 C11 C12 C13 . . . . 1.6(3) ?
C11 C12 C13 C16 . . . . -0.2(3) ?
O4 N2 C14 C15 . . . . -168.66(14) ?
O5 N2 C14 C15 . . . . 9.9(2) ?
O4 N2 C14 C7 . . . . 10.2(2) ?
O5 N2 C14 C7 . . . . -171.17(13) ?
C6 C7 C14 C15 . . . . -136.21(15) ?
C8 C7 C14 C15 . . . . -15.60(19) ?
C6 C7 C14 N2 . . . . 44.98(19) ?
C8 C7 C14 N2 . . . . 165.60(13) ?
C18 N1 C15 C14 . . . . 171.03(14) ?
C9 N1 C15 C14 . . . . -2.4(2) ?
N2 C14 C15 N1 . . . . 170.13(14) ?
C7 C14 C15 N1 . . . . -8.7(2) ?
C12 C13 C16 F1 . . . . 178.33(16) ?
C12 C13 C16 C17 . . . . -1.1(3) ?
F1 C16 C17 C10 . . . . -178.47(14) ?
C13 C16 C17 C10 . . . . 1.0(3) ?
F1 C16 C17 C18 . . . . -3.0(3) ?
C13 C16 C17 C18 . . . . 176.43(17) ?
C11 C10 C17 C16 . . . . 0.5(2) ?
C9 C10 C17 C16 . . . . 177.46(14) ?
C11 C10 C17 C18 . . . . -175.74(15) ?
C9 C10 C17 C18 . . . . 1.25(18) ?
C15 N1 C18 C17 . . . . -160.70(14) ?
C9 N1 C18 C17 . . . . 13.16(16) ?
C16 C17 C18 N1 . . . . 175.85(16) ?
C10 C17 C18 N1 . . . . -8.43(17) ?
C9 C8 C19 O3 . . . . 68.56(18) ?
C7 C8 C19 O3 . . . . -51.79(19) ?
C9 C8 C19 C20 . . . . -106.63(16) ?
C7 C8 C19 C20 . . . . 133.02(15) ?
O3 C19 C20 C25 . . . . 166.90(16) ?
C8 C19 C20 C25 . . . . -18.0(2) ?
O3 C19 C20 C21 . . . . -14.1(2) ?
C8 C19 C20 C21 . . . . 161.05(15) ?
C25 C20 C21 C22 . . . . 0.5(3) ?
C19 C20 C21 C22 . . . . -178.61(15) ?
C20 C21 C22 C23 . . . . -1.2(3) ?
C21 C22 C23 C24 . . . . 0.6(3) ?
C22 C23 C24 C25 . . . . 0.7(3) ?
C21 C20 C25 C24 . . . . 0.8(2) ?
C19 C20 C25 C24 . . . . 179.80(15) ?
C23 C24 C25 C20 . . . . -1.3(3) ?



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

data_wll148
_database_code_depnum_ccdc_archive 'CCDC 2071232'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H23 N3 O4'
_chemical_formula_sum            'C26 H23 N3 O4'
_chemical_formula_weight         441.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4
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           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                   14.0994(5)
_cell_length_b                   10.9354(3)
_cell_length_c                   16.3508(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.198(4)
_cell_angle_gamma                90
_cell_volume                     2281.11(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3790
_cell_measurement_theta_min      5.0380
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         5.029
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  35.00   1.00    2.10    --  -33.50  57.00   0.00   87
  2  ω     -4.00  77.00   1.00    2.10    --   36.47 -99.00 150.00   81
  3  ω     58.00  92.00   1.00    2.10    --   36.47 178.00 -60.00   34
  4  ω     66.00  96.00   1.00    2.10    --   36.47 178.00-150.00   30
  5  ω     76.00 110.00   1.00    2.10    --   36.47 178.00  90.00   34
  6  ω     -1.00  77.00   1.00    2.10    --   36.47 -99.00 -60.00   78
  7  ω      9.00  38.00   1.00    2.10    --   36.47  77.00  90.00   29
  8  ω     63.00 104.00   1.00    2.10    --   36.47  77.00  90.00   41
  9  ω     47.00  73.00   1.00   14.50    --  108.00 -30.00-150.00   26
 10  ω     78.00 118.00   1.00   14.50    --  108.00 -45.00 150.00   40
 11  ω     46.00 103.00   1.00   14.50    --  108.00 -94.00-180.00   57
 12  ω     98.00 127.00   1.00   14.50    --  108.00 -30.00-150.00   29
 13  ω    113.00 172.00   1.00   14.50    --  108.00 111.00 150.00   59
 14  ω     96.00 173.00   1.00   14.50    --  108.00  61.00 -60.00   77
 15  ω     45.00 109.00   1.00   14.50    --  108.00 -45.00   0.00   64
 16  ω     63.00 178.00   1.00   14.50    --  108.00  15.00-120.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0864300000
_diffrn_orient_matrix_UB_12      -0.0927519000
_diffrn_orient_matrix_UB_13      0.0536231000
_diffrn_orient_matrix_UB_21      -0.0744726000
_diffrn_orient_matrix_UB_22      -0.0620072000
_diffrn_orient_matrix_UB_23      0.0341683000
_diffrn_orient_matrix_UB_31      -0.0395202000
_diffrn_orient_matrix_UB_32      -0.0860887000
_diffrn_orient_matrix_UB_33      -0.0824242000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3204
_reflns_number_total             4065
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.028
_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)+(0.0652P)²+0.2535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1275
_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
 C24-N3A
 1.45 with sigma of 0.02
 O4A-N3A
 1.4 with sigma of 0.02
 N2A-C11
 1.45 with sigma of 0.02
 N2A-O2A
 1.2 with sigma of 0.02
3. Rigid bond restraints
 N3, O4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N2, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O4) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O4) = Uanis(O4A)
Uanis(N3) = Uanis(N3A)
Uanis(O2) = Uanis(O2A)
Uanis(O1) = Uanis(O1A)
Uanis(N2) = Uanis(N2A)
5. Others
 Sof(O4A)=Sof(N3A)=1-FVAR(1)
 Sof(O4)=Sof(N3)=FVAR(1)
 Sof(O2A)=Sof(O1A)=Sof(N2A)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(N2)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
6.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03814(17) 0.5433(7) 0.65287(18) 0.0699(10) Uani 0.92(2) 1 d . . P A 1
O2 O 0.0891(2) 0.6671(4) 0.5752(3) 0.0639(7) Uani 0.92(2) 1 d . U P A 1
O3 O 0.37199(10) 0.34646(13) 0.47997(10) 0.0656(4) Uani 1 1 d . . . . .
O4 O 0.5909(4) 0.8099(6) 0.6757(3) 0.0577(12) Uani 0.644(16) 1 d . U P B 1
N1 N 0.16516(12) 0.25297(14) 0.58593(10) 0.0534(4) Uani 1 1 d . . . . .
N2 N 0.0863(3) 0.5620(3) 0.6046(3) 0.0518(7) Uani 0.92(2) 1 d . U P A 1
N3 N 0.6083(5) 0.7399(7) 0.7532(6) 0.0555(14) Uani 0.644(16) 1 d . U P B 1
C1 C 0.1393(2) -0.0586(2) 0.4986(2) 0.0860(8) Uani 1 1 d . . . . .
H1 H 0.1131 -0.1124 0.5280 0.103 Uiso 1 1 calc R . . . .
C2 C 0.1548(2) -0.0963(2) 0.4252(2) 0.0944(9) Uani 1 1 d . . . . .
H2 H 0.1377 -0.1760 0.4042 0.113 Uiso 1 1 calc R . . . .
C3 C 0.1953(2) -0.0176(2) 0.38189(19) 0.0884(8) Uani 1 1 d . . . . .
H3 H 0.2043 -0.0447 0.3317 0.106 Uiso 1 1 calc R . . . .
C4 C 0.22275(18) 0.1019(2) 0.41272(15) 0.0689(5) Uani 1 1 d . . . . .
H4 H 0.2515 0.1545 0.3846 0.083 Uiso 1 1 calc R . . . .
C5 C 0.20604(14) 0.14003(16) 0.48610(13) 0.0550(4) Uani 1 1 d . . . . .
C6 C 0.16332(15) 0.06104(19) 0.52813(15) 0.0655(5) Uani 1 1 d . . . . .
C7 C 0.15004(17) 0.12451(19) 0.60367(15) 0.0681(6) Uani 1 1 d . . . . .
H7A H 0.0807 0.1109 0.6008 0.082 Uiso 1 1 calc R . . . .
H7B H 0.2024 0.0981 0.6621 0.082 Uiso 1 1 calc R . . . .
C8 C 0.22872(12) 0.26225(15) 0.53434(11) 0.0459(4) Uani 1 1 d . . . . .
H8 H 0.3029 0.2644 0.5771 0.055 Uiso 1 1 calc R . . . .
C9 C 0.20345(12) 0.37802(14) 0.47686(11) 0.0418(3) Uani 1 1 d . . . . .
H9 H 0.1359 0.3681 0.4243 0.050 Uiso 1 1 calc R . . . .
C10 C 0.19945(12) 0.49340(14) 0.53176(11) 0.0425(3) Uani 1 1 d . . . . .
H10 H 0.1648 0.5594 0.4888 0.051 Uiso 1 1 calc R . . . .
C11 C 0.13456(12) 0.46463(16) 0.58166(11) 0.0471(4) Uani 1 1 d D . . . .
C12 C 0.12248(13) 0.34853(18) 0.60606(12) 0.0526(4) Uani 1 1 d . . . . .
H12 H 0.0825 0.3364 0.6382 0.063 Uiso 1 1 calc R . . . .
C13 C 0.28917(13) 0.40021(15) 0.44476(12) 0.0471(4) Uani 1 1 d . . . . .
C14 C 0.27313(14) 0.49498(15) 0.37467(12) 0.0494(4) Uani 1 1 d . . . . .
C15 C 0.17528(16) 0.54052(19) 0.31781(13) 0.0597(5) Uani 1 1 d . . . . .
H15 H 0.1155 0.5108 0.3215 0.072 Uiso 1 1 calc R . . . .
C16 C 0.1669(2) 0.6307(2) 0.25521(15) 0.0748(6) Uani 1 1 d . . . . .
H16 H 0.1013 0.6610 0.2168 0.090 Uiso 1 1 calc R . . . .
C17 C 0.2555(2) 0.6755(2) 0.24989(18) 0.0827(7) Uani 1 1 d . . . . .
H17 H 0.2496 0.7364 0.2082 0.099 Uiso 1 1 calc R . . . .
C18 C 0.3526(2) 0.6303(2) 0.3061(2) 0.0833(7) Uani 1 1 d . . . . .
H18 H 0.4123 0.6604 0.3022 0.100 Uiso 1 1 calc R . . . .
C19 C 0.36178(18) 0.54068(19) 0.36825(16) 0.0647(5) Uani 1 1 d . . . . .
H19 H 0.4276 0.5105 0.4061 0.078 Uiso 1 1 calc R . . . .
C20 C 0.30715(12) 0.53676(15) 0.59563(11) 0.0454(4) Uani 1 1 d . . . . .
H20 H 0.3482 0.4859 0.6432 0.054 Uiso 1 1 calc R . . . .
C21 C 0.34598(13) 0.64322(15) 0.58740(12) 0.0465(4) Uani 1 1 d . . . . .
H21 H 0.3022 0.6927 0.5402 0.056 Uiso 1 1 calc R . . . .
C22 C 0.52020(14) 0.66567(17) 0.73192(12) 0.0534(4) Uani 1 1 d . . . . .
C23 C 0.44943(13) 0.69252(15) 0.64357(12) 0.0462(4) Uani 1 1 d . . . . .
C24 C 0.50008(14) 0.78096(16) 0.61666(13) 0.0519(4) Uani 1 1 d D . . . .
C25 C 0.51349(19) 0.5802(2) 0.79967(15) 0.0762(6) Uani 1 1 d . . . . .
H25A H 0.5251 0.4981 0.7852 0.114 Uiso 1 1 calc GR . . . .
H25B H 0.4452 0.5860 0.7990 0.114 Uiso 1 1 calc GR . . . .
H25C H 0.5658 0.6013 0.8587 0.114 Uiso 1 1 calc GR . . . .
C26 C 0.46731(17) 0.8468(2) 0.52998(16) 0.0682(5) Uani 1 1 d . . . . .
H26A H 0.4119 0.9028 0.5228 0.102 Uiso 1 1 calc GR . . . .
H26B H 0.4429 0.7892 0.4811 0.102 Uiso 1 1 calc GR . . . .
H26C H 0.5259 0.8914 0.5297 0.102 Uiso 1 1 calc GR . . . .
O4A O 0.6033(10) 0.7187(10) 0.7624(11) 0.0577(12) Uani 0.356(16) 1 d D . P B 2
N3A N 0.5982(8) 0.7984(16) 0.6957(10) 0.0555(14) Uani 0.356(16) 1 d D . P B 2
O2A O 0.098(3) 0.641(4) 0.597(4) 0.0639(7) Uani 0.08(2) 1 d D . P A 2
O1A O 0.034(2) 0.491(6) 0.660(2) 0.0699(10) Uani 0.08(2) 1 d . . P A 2
N2A N 0.071(3) 0.541(4) 0.612(3) 0.0518(7) Uani 0.08(2) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.257(3) . ?
O2 N2 1.253(3) . ?
O3 C13 1.212(2) . ?
O4 N3 1.410(5) . ?
O4 C24 1.272(6) . ?
N1 C7 1.468(2) . ?
N1 C8 1.473(2) . ?
N1 C12 1.316(3) . ?
N2 C11 1.399(3) . ?
N3 C22 1.398(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(4) . ?
C1 C6 1.386(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 C6 1.391(3) . ?
C5 C8 1.515(2) . ?
C6 C7 1.497(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C8 C9 1.526(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.563(2) . ?
C9 C13 1.528(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.496(2) . ?
C10 C20 1.507(2) . ?
C11 C12 1.363(3) . ?
C11 N2A 1.46(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.489(2) . ?
C14 C15 1.387(3) . ?
C14 C19 1.391(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.318(2) . ?
C21 H21 0.9300 . ?
C21 C23 1.456(2) . ?
C22 C23 1.393(3) . ?
C22 C25 1.483(3) . ?
C22 O4A 1.209(11) . ?
C23 C24 1.381(2) . ?
C24 C26 1.478(3) . ?
C24 N3A 1.448(9) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O4A N3A 1.374(10) . ?
O2A N2A 1.21(2) . ?
O1A N2A 1.23(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 O4 N3 106.3(5) . . ?
C7 N1 C8 110.74(16) . . ?
C12 N1 C7 126.16(16) . . ?
C12 N1 C8 122.91(15) . . ?
O1 N2 C11 119.9(2) . . ?
O2 N2 O1 120.3(4) . . ?
O2 N2 C11 119.7(4) . . ?
C22 N3 O4 107.2(6) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.8(3) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 120.77(19) . . ?
C4 C5 C8 129.93(18) . . ?
C6 C5 C8 109.30(18) . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 C7 128.9(2) . . ?
C5 C6 C7 110.64(18) . . ?
N1 C7 C6 101.59(16) . . ?
N1 C7 H7A 111.5 . . ?
N1 C7 H7B 111.5 . . ?
C6 C7 H7A 111.5 . . ?
C6 C7 H7B 111.5 . . ?
H7A C7 H7B 109.3 . . ?
N1 C8 C5 101.09(14) . . ?
N1 C8 H8 108.5 . . ?
N1 C8 C9 111.75(14) . . ?
C5 C8 H8 108.5 . . ?
C5 C8 C9 117.97(14) . . ?
C9 C8 H8 108.5 . . ?
C8 C9 H9 109.4 . . ?
C8 C9 C10 111.83(13) . . ?
C8 C9 C13 109.38(13) . . ?
C10 C9 H9 109.4 . . ?
C13 C9 H9 109.4 . . ?
C13 C9 C10 107.23(13) . . ?
C9 C10 H10 108.2 . . ?
C11 C10 C9 108.87(13) . . ?
C11 C10 H10 108.2 . . ?
C11 C10 C20 110.98(13) . . ?
C20 C10 C9 112.32(13) . . ?
C20 C10 H10 108.2 . . ?
N2 C11 C10 117.9(3) . . ?
C12 C11 N2 119.6(3) . . ?
C12 C11 C10 122.50(16) . . ?
C12 C11 N2A 105(2) . . ?
N2A C11 C10 132(2) . . ?
N1 C12 C11 122.61(16) . . ?
N1 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
O3 C13 C9 120.19(15) . . ?
O3 C13 C14 120.21(16) . . ?
C14 C13 C9 119.44(14) . . ?
C15 C14 C13 123.20(16) . . ?
C15 C14 C19 119.32(18) . . ?
C19 C14 C13 117.46(17) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C10 C20 H20 118.4 . . ?
C21 C20 C10 123.18(15) . . ?
C21 C20 H20 118.4 . . ?
C20 C21 H21 116.2 . . ?
C20 C21 C23 127.65(16) . . ?
C23 C21 H21 116.2 . . ?
N3 C22 C25 120.8(4) . . ?
C23 C22 N3 107.7(4) . . ?
C23 C22 C25 131.46(17) . . ?
O4A C22 C23 117.9(8) . . ?
O4A C22 C25 110.7(8) . . ?
C22 C23 C21 131.20(16) . . ?
C24 C23 C21 124.99(17) . . ?
C24 C23 C22 103.81(16) . . ?
O4 C24 C23 115.0(4) . . ?
O4 C24 C26 114.1(3) . . ?
C23 C24 C26 130.85(18) . . ?
C23 C24 N3A 103.6(8) . . ?
N3A C24 C26 125.6(9) . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 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 . . ?
C22 O4A N3A 105.2(13) . . ?
O4A N3A C24 109.4(13) . . ?
O2A N2A C11 99(3) . . ?
O2A N2A O1A 141(4) . . ?
O1A N2A C11 117(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
O1 N2 C11 C10 -174.2(2) . . . . ?
O1 N2 C11 C12 4.9(4) . . . . ?
O2 N2 C11 C10 7.5(5) . . . . ?
O2 N2 C11 C12 -173.4(3) . . . . ?
O3 C13 C14 C15 165.34(19) . . . . ?
O3 C13 C14 C19 -16.0(3) . . . . ?
O4 N3 C22 C23 -1.4(4) . . . . ?
O4 N3 C22 C25 -179.9(3) . . . . ?
N1 C8 C9 C10 46.75(18) . . . . ?
N1 C8 C9 C13 165.40(13) . . . . ?
N2 C11 C12 N1 179.5(2) . . . . ?
N3 O4 C24 C23 -1.5(4) . . . . ?
N3 O4 C24 C26 179.4(3) . . . . ?
N3 C22 C23 C21 -180.0(4) . . . . ?
N3 C22 C23 C24 0.6(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C1 C6 C7 N1 -166.9(2) . . . . ?
C2 C1 C6 C5 -2.4(3) . . . . ?
C2 C1 C6 C7 177.7(2) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C8 179.35(19) . . . . ?
C4 C5 C6 C1 1.7(3) . . . . ?
C4 C5 C6 C7 -178.31(18) . . . . ?
C4 C5 C8 N1 164.00(19) . . . . ?
C4 C5 C8 C9 41.9(3) . . . . ?
C5 C6 C7 N1 13.1(2) . . . . ?
C5 C8 C9 C10 163.27(15) . . . . ?
C5 C8 C9 C13 -78.09(18) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C6 C5 C8 N1 -16.78(18) . . . . ?
C6 C5 C8 C9 -138.90(16) . . . . ?
C7 N1 C8 C5 25.92(18) . . . . ?
C7 N1 C8 C9 152.28(15) . . . . ?
C7 N1 C12 C11 -175.27(17) . . . . ?
C8 N1 C7 C6 -24.67(19) . . . . ?
C8 N1 C12 C11 -0.8(3) . . . . ?
C8 C5 C6 C1 -177.57(18) . . . . ?
C8 C5 C6 C7 2.4(2) . . . . ?
C8 C9 C10 C11 -47.43(17) . . . . ?
C8 C9 C10 C20 75.90(17) . . . . ?
C8 C9 C13 O3 -15.1(2) . . . . ?
C8 C9 C13 C14 169.40(14) . . . . ?
C9 C10 C11 N2 -155.0(2) . . . . ?
C9 C10 C11 C12 25.9(2) . . . . ?
C9 C10 C11 N2A -152(3) . . . . ?
C9 C10 C20 C21 115.10(18) . . . . ?
C9 C13 C14 C15 -19.1(3) . . . . ?
C9 C13 C14 C19 159.51(17) . . . . ?
C10 C9 C13 O3 106.37(19) . . . . ?
C10 C9 C13 C14 -69.14(18) . . . . ?
C10 C11 C12 N1 -1.4(3) . . . . ?
C10 C11 N2A O2A -10(6) . . . . ?
C10 C11 N2A O1A -173(2) . . . . ?
C10 C20 C21 C23 -178.30(16) . . . . ?
C11 C10 C20 C21 -122.76(18) . . . . ?
C12 N1 C7 C6 150.39(18) . . . . ?
C12 N1 C8 C5 -149.33(16) . . . . ?
C12 N1 C8 C9 -23.0(2) . . . . ?
C12 C11 N2A O2A 172(4) . . . . ?
C12 C11 N2A O1A 9(4) . . . . ?
C13 C9 C10 C11 -167.34(13) . . . . ?
C13 C9 C10 C20 -44.01(17) . . . . ?
C13 C14 C15 C16 178.75(18) . . . . ?
C13 C14 C19 C18 -178.7(2) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C14 0.1(4) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
C20 C10 C11 N2 80.9(2) . . . . ?
C20 C10 C11 C12 -98.21(18) . . . . ?
C20 C10 C11 N2A 84(3) . . . . ?
C20 C21 C23 C22 -22.8(3) . . . . ?
C20 C21 C23 C24 156.53(18) . . . . ?
C21 C23 C24 O4 -178.9(3) . . . . ?
C21 C23 C24 C26 0.0(3) . . . . ?
C21 C23 C24 N3A 179.7(6) . . . . ?
C22 C23 C24 O4 0.6(3) . . . . ?
C22 C23 C24 C26 179.5(2) . . . . ?
C22 C23 C24 N3A -0.9(6) . . . . ?
C22 O4A N3A C24 -3.1(10) . . . . ?
C23 C22 O4A N3A 2.7(9) . . . . ?
C23 C24 N3A O4A 2.4(9) . . . . ?
C24 O4 N3 C22 1.8(4) . . . . ?
C25 C22 C23 C21 -1.7(4) . . . . ?
C25 C22 C23 C24 178.8(2) . . . . ?
C25 C22 O4A N3A -177.3(6) . . . . ?
C26 C24 N3A O4A -177.9(5) . . . . ?
O4A C22 C23 C21 178.2(7) . . . . ?
O4A C22 C23 C24 -1.2(7) . . . . ?
N2A C11 C12 N1 177(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.919
####################################################################### 
# 
# 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_hd_wql32
_database_code_depnum_ccdc_archive 'CCDC 2086416'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H24 N2 O5'
_chemical_formula_sum            'C25 H24 N2 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         432.46

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   25.4779(15)
_cell_length_b                   11.8085(6)
_cell_length_c                   13.8705(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4173.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      3.4695
_cell_measurement_theta_max      72.4255
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824

_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            45327
_diffrn_reflns_av_R_equivalents  0.1556
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         72.73
_diffrn_reflns_theta_full        72.73
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4147
_reflns_number_gt                3183
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2225
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         4147
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1569P)²+0.5614P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.462
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0008(3)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.51621(7) 0.86936(16) 0.57694(13) 0.0320(4) Uani d . . . 1 . .
O O2 0.52499(8) 0.76466(18) 0.44214(14) 0.0367(5) Uani d . . . 1 . .
O O3 0.81679(9) 0.79248(18) 0.32222(16) 0.0448(6) Uani d . . . 1 . .
O O4 0.79965(8) 0.62734(17) 0.25898(13) 0.0345(5) Uani d . . . 1 . .
O O5 0.73013(8) 0.53745(15) 0.58533(14) 0.0341(5) Uani d . . . 1 . .
N N1 0.66848(8) 0.60215(17) 0.41986(15) 0.0260(5) Uani d . . . 1 . .
N N2 0.78896(9) 0.70482(19) 0.31735(15) 0.0309(5) Uani d . . . 1 . .
C C1 0.43772(12) 0.8975(3) 0.6666(2) 0.0397(7) Uani d . . . 1 . .
H H1 0.454784 0.872121 0.726095 0.06 Uiso calc U . R 1 . .
H H4 0.400072 0.881008 0.669927 0.06 Uiso calc U . R 1 . .
H H3 0.442908 0.979281 0.658916 0.06 Uiso calc U . R 1 . .
C C2 0.46131(11) 0.8366(3) 0.5821(2) 0.0362(6) Uani d . . . 1 . .
H H23 0.458203 0.753666 0.590796 0.043 Uiso calc U . R 1 . .
H H24 0.442922 0.858007 0.521885 0.043 Uiso calc U . R 1 . .
C C3 0.54358(10) 0.8259(2) 0.50235(18) 0.0289(6) Uani d . . . 1 . .
C C4 0.59951(10) 0.8679(2) 0.50489(18) 0.0282(5) Uani d . . . 1 . .
H H21 0.611932 0.867113 0.572516 0.034 Uiso calc U . R 1 . .
H H22 0.600182 0.947458 0.482352 0.034 Uiso calc U . R 1 . .
C C5 0.63739(10) 0.7989(2) 0.44363(17) 0.0267(5) Uani d . . . 1 . .
H H5 0.61953 0.776897 0.382214 0.032 Uiso calc U . R 1 . .
C C6 0.65765(10) 0.6887(2) 0.49574(17) 0.0265(5) Uani d . . . 1 . .
C C7 0.70974(10) 0.7276(2) 0.53986(18) 0.0251(5) Uani d . . . 1 . .
H H11 0.702087 0.785814 0.590306 0.03 Uiso calc U . R 1 . .
C C8 0.74373(10) 0.6366(2) 0.58405(17) 0.0264(5) Uani d . . . 1 . .
C C9 0.79605(10) 0.6714(2) 0.62284(17) 0.0268(5) Uani d . . . 1 . .
C C10 0.83391(10) 0.5881(2) 0.63798(17) 0.0280(5) Uani d . . . 1 . .
H H14 0.825403 0.510731 0.627696 0.034 Uiso calc U . R 1 . .
C C11 0.88402(11) 0.6180(2) 0.66805(18) 0.0313(6) Uani d . . . 1 . .
H H15 0.909971 0.561088 0.676776 0.038 Uiso calc U . R 1 . .
C C12 0.89629(10) 0.7306(2) 0.68539(19) 0.0318(6) Uani d . . . 1 . .
H H2 0.930712 0.750999 0.70518 0.038 Uiso calc U . R 1 . .
C C13 0.61809(10) 0.6273(2) 0.55624(18) 0.0265(5) Uani d . . . 1 . .
C C14 0.59995(10) 0.6562(2) 0.64744(19) 0.0278(5) Uani d . . . 1 . .
H H20 0.614592 0.718318 0.681657 0.033 Uiso calc U . R 1 . .
C C15 0.55969(10) 0.5916(2) 0.68730(19) 0.0299(6) Uani d . . . 1 . .
H H6 0.546641 0.609841 0.749546 0.036 Uiso calc U . R 1 . .
C C16 0.53835(10) 0.5006(2) 0.6371(2) 0.0319(6) Uani d . . . 1 . .
H H7 0.509955 0.459282 0.664231 0.038 Uiso calc U . R 1 . .
C C17 0.55827(10) 0.4695(2) 0.54747(19) 0.0292(5) Uani d . . . 1 . .
H H8 0.544477 0.406035 0.51387 0.035 Uiso calc U . R 1 . .
C C18 0.59860(10) 0.5331(2) 0.50841(18) 0.0269(5) Uani d . . . 1 . .
C C19 0.62776(11) 0.5144(2) 0.41524(19) 0.0307(6) Uani d . . . 1 . .
H H10 0.643342 0.437687 0.41252 0.037 Uiso calc U . R 1 . .
H H9 0.604544 0.525424 0.358779 0.037 Uiso calc U . R 1 . .
C C20 0.71151(10) 0.6072(2) 0.36648(17) 0.0271(5) Uani d . . . 1 . .
H H19 0.718711 0.5497 0.32046 0.033 Uiso calc U . R 1 . .
C C21 0.74578(10) 0.6964(2) 0.37809(17) 0.0280(5) Uani d . . . 1 . .
C C22 0.73417(10) 0.7882(2) 0.45091(17) 0.0278(5) Uani d . . . 1 . .
H H16 0.766267 0.832446 0.468302 0.033 Uiso calc U . R 1 . .
C C23 0.80823(10) 0.7850(2) 0.64181(18) 0.0283(5) Uani d . . . 1 . .
H H12 0.782466 0.842178 0.632834 0.034 Uiso calc U . R 1 . .
C C24 0.85812(11) 0.8135(2) 0.67375(18) 0.0301(6) Uani d . . . 1 . .
H H13 0.866232 0.890267 0.68777 0.036 Uiso calc U . R 1 . .
C C25 0.68871(10) 0.8652(2) 0.41916(18) 0.0284(5) Uani d . . . 1 . .
H H17 0.690778 0.880884 0.349143 0.034 Uiso calc U . R 1 . .
H H18 0.689785 0.938051 0.454442 0.034 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.349(3) ?
O1 C2 . 1.453(3) ?
O2 C3 . 1.202(3) ?
O3 N2 . 1.256(3) ?
O4 N2 . 1.252(3) ?
O5 C8 . 1.222(3) ?
N1 C20 . 1.324(3) ?
N1 C19 . 1.467(3) ?
N1 C6 . 1.493(3) ?
N2 C21 . 1.389(3) ?
C1 C2 . 1.501(4) ?
C1 H1 . 0.98 ?
C1 H4 . 0.98 ?
C1 H3 . 0.98 ?
C2 H23 . 0.99 ?
C2 H24 . 0.99 ?
C3 C4 . 1.509(4) ?
C4 C5 . 1.523(3) ?
C4 H21 . 0.99 ?
C4 H22 . 0.99 ?
C5 C25 . 1.562(3) ?
C5 C6 . 1.575(3) ?
C5 H5 . 1.0 ?
C6 C13 . 1.499(3) ?
C6 C7 . 1.532(3) ?
C7 C8 . 1.510(3) ?
C7 C22 . 1.556(3) ?
C7 H11 . 1.0 ?
C8 C9 . 1.495(3) ?
C9 C10 . 1.394(4) ?
C9 C23 . 1.401(3) ?
C10 C11 . 1.389(4) ?
C10 H14 . 0.95 ?
C11 C12 . 1.387(4) ?
C11 H15 . 0.95 ?
C12 C24 . 1.389(4) ?
C12 H2 . 0.95 ?
C13 C18 . 1.387(4) ?
C13 C14 . 1.389(4) ?
C14 C15 . 1.393(4) ?
C14 H20 . 0.95 ?
C15 C16 . 1.391(4) ?
C15 H6 . 0.95 ?
C16 C17 . 1.392(4) ?
C16 H7 . 0.95 ?
C17 C18 . 1.383(4) ?
C17 H8 . 0.95 ?
C18 C19 . 1.507(4) ?
C19 H10 . 0.99 ?
C19 H9 . 0.99 ?
C20 C21 . 1.378(3) ?
C20 H19 . 0.95 ?
C21 C22 . 1.511(3) ?
C22 C25 . 1.537(3) ?
C22 H16 . 1.0 ?
C23 C24 . 1.387(4) ?
C23 H12 . 0.95 ?
C24 H13 . 0.95 ?
C25 H17 . 0.99 ?
C25 H18 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C2 . . 115.7(2) ?
C20 N1 C19 . . 126.4(2) ?
C20 N1 C6 . . 121.1(2) ?
C19 N1 C6 . . 112.6(2) ?
O4 N2 O3 . . 121.0(2) ?
O4 N2 C21 . . 120.8(2) ?
O3 N2 C21 . . 118.2(2) ?
C2 C1 H1 . . 109.5 ?
C2 C1 H4 . . 109.5 ?
H1 C1 H4 . . 109.5 ?
C2 C1 H3 . . 109.5 ?
H1 C1 H3 . . 109.5 ?
H4 C1 H3 . . 109.5 ?
O1 C2 C1 . . 107.2(2) ?
O1 C2 H23 . . 110.3 ?
C1 C2 H23 . . 110.3 ?
O1 C2 H24 . . 110.3 ?
C1 C2 H24 . . 110.3 ?
H23 C2 H24 . . 108.5 ?
O2 C3 O1 . . 123.9(2) ?
O2 C3 C4 . . 125.9(2) ?
O1 C3 C4 . . 110.2(2) ?
C3 C4 C5 . . 114.2(2) ?
C3 C4 H21 . . 108.7 ?
C5 C4 H21 . . 108.7 ?
C3 C4 H22 . . 108.7 ?
C5 C4 H22 . . 108.7 ?
H21 C4 H22 . . 107.6 ?
C4 C5 C25 . . 112.5(2) ?
C4 C5 C6 . . 113.2(2) ?
C25 C5 C6 . . 103.87(19) ?
C4 C5 H5 . . 109.0 ?
C25 C5 H5 . . 109.0 ?
C6 C5 H5 . . 109.0 ?
N1 C6 C13 . . 100.81(19) ?
N1 C6 C7 . . 109.07(19) ?
C13 C6 C7 . . 120.3(2) ?
N1 C6 C5 . . 107.61(19) ?
C13 C6 C5 . . 115.9(2) ?
C7 C6 C5 . . 102.69(19) ?
C8 C7 C6 . . 116.5(2) ?
C8 C7 C22 . . 114.8(2) ?
C6 C7 C22 . . 99.65(19) ?
C8 C7 H11 . . 108.5 ?
C6 C7 H11 . . 108.5 ?
C22 C7 H11 . . 108.5 ?
O5 C8 C9 . . 120.7(2) ?
O5 C8 C7 . . 121.7(2) ?
C9 C8 C7 . . 117.5(2) ?
C10 C9 C23 . . 119.6(2) ?
C10 C9 C8 . . 118.5(2) ?
C23 C9 C8 . . 121.9(2) ?
C11 C10 C9 . . 120.2(2) ?
C11 C10 H14 . . 119.9 ?
C9 C10 H14 . . 119.9 ?
C12 C11 C10 . . 120.2(2) ?
C12 C11 H15 . . 119.9 ?
C10 C11 H15 . . 119.9 ?
C11 C12 C24 . . 119.8(2) ?
C11 C12 H2 . . 120.1 ?
C24 C12 H2 . . 120.1 ?
C18 C13 C14 . . 120.9(2) ?
C18 C13 C6 . . 111.2(2) ?
C14 C13 C6 . . 127.9(2) ?
C13 C14 C15 . . 118.1(2) ?
C13 C14 H20 . . 120.9 ?
C15 C14 H20 . . 120.9 ?
C16 C15 C14 . . 120.8(2) ?
C16 C15 H6 . . 119.6 ?
C14 C15 H6 . . 119.6 ?
C15 C16 C17 . . 120.5(2) ?
C15 C16 H7 . . 119.7 ?
C17 C16 H7 . . 119.7 ?
C18 C17 C16 . . 118.5(2) ?
C18 C17 H8 . . 120.7 ?
C16 C17 H8 . . 120.7 ?
C17 C18 C13 . . 120.9(2) ?
C17 C18 C19 . . 128.5(2) ?
C13 C18 C19 . . 110.6(2) ?
N1 C19 C18 . . 102.0(2) ?
N1 C19 H10 . . 111.4 ?
C18 C19 H10 . . 111.4 ?
N1 C19 H9 . . 111.4 ?
C18 C19 H9 . . 111.4 ?
H10 C19 H9 . . 109.2 ?
N1 C20 C21 . . 119.6(2) ?
N1 C20 H19 . . 120.2 ?
C21 C20 H19 . . 120.2 ?
C20 C21 N2 . . 119.0(2) ?
C20 C21 C22 . . 120.2(2) ?
N2 C21 C22 . . 120.6(2) ?
C21 C22 C25 . . 112.4(2) ?
C21 C22 C7 . . 106.2(2) ?
C25 C22 C7 . . 101.41(19) ?
C21 C22 H16 . . 112.1 ?
C25 C22 H16 . . 112.1 ?
C7 C22 H16 . . 112.1 ?
C24 C23 C9 . . 119.7(2) ?
C24 C23 H12 . . 120.2 ?
C9 C23 H12 . . 120.2 ?
C23 C24 C12 . . 120.5(2) ?
C23 C24 H13 . . 119.8 ?
C12 C24 H13 . . 119.8 ?
C22 C25 C5 . . 105.77(19) ?
C22 C25 H17 . . 110.6 ?
C5 C25 H17 . . 110.6 ?
C22 C25 H18 . . 110.6 ?
C5 C25 H18 . . 110.6 ?
H17 C25 H18 . . 108.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 O1 C2 C1 . . . . -177.5(2) ?
C2 O1 C3 O2 . . . . 0.7(4) ?
C2 O1 C3 C4 . . . . 179.2(2) ?
O2 C3 C4 C5 . . . . -18.7(4) ?
O1 C3 C4 C5 . . . . 162.8(2) ?
C3 C4 C5 C25 . . . . 160.3(2) ?
C3 C4 C5 C6 . . . . -82.3(3) ?
C20 N1 C6 C13 . . . . -160.9(2) ?
C19 N1 C6 C13 . . . . 17.6(3) ?
C20 N1 C6 C7 . . . . -33.4(3) ?
C19 N1 C6 C7 . . . . 145.1(2) ?
C20 N1 C6 C5 . . . . 77.3(3) ?
C19 N1 C6 C5 . . . . -104.1(2) ?
C4 C5 C6 N1 . . . . 149.9(2) ?
C25 C5 C6 N1 . . . . -87.7(2) ?
C4 C5 C6 C13 . . . . 38.0(3) ?
C25 C5 C6 C13 . . . . 160.4(2) ?
C4 C5 C6 C7 . . . . -95.1(2) ?
C25 C5 C6 C7 . . . . 27.3(2) ?
N1 C6 C7 C8 . . . . -57.6(3) ?
C13 C6 C7 C8 . . . . 57.9(3) ?
C5 C6 C7 C8 . . . . -171.6(2) ?
N1 C6 C7 C22 . . . . 66.4(2) ?
C13 C6 C7 C22 . . . . -178.0(2) ?
C5 C6 C7 C22 . . . . -47.5(2) ?
C6 C7 C8 O5 . . . . -0.7(3) ?
C22 C7 C8 O5 . . . . -116.6(3) ?
C6 C7 C8 C9 . . . . 176.8(2) ?
C22 C7 C8 C9 . . . . 60.9(3) ?
O5 C8 C9 C10 . . . . 15.8(4) ?
C7 C8 C9 C10 . . . . -161.7(2) ?
O5 C8 C9 C23 . . . . -165.8(2) ?
C7 C8 C9 C23 . . . . 16.7(3) ?
C23 C9 C10 C11 . . . . -2.5(4) ?
C8 C9 C10 C11 . . . . 175.9(2) ?
C9 C10 C11 C12 . . . . 1.5(4) ?
C10 C11 C12 C24 . . . . 0.8(4) ?
N1 C6 C13 C18 . . . . -14.3(3) ?
C7 C6 C13 C18 . . . . -134.0(2) ?
C5 C6 C13 C18 . . . . 101.5(2) ?
N1 C6 C13 C14 . . . . 167.4(2) ?
C7 C6 C13 C14 . . . . 47.7(4) ?
C5 C6 C13 C14 . . . . -76.8(3) ?
C18 C13 C14 C15 . . . . -3.4(4) ?
C6 C13 C14 C15 . . . . 174.8(2) ?
C13 C14 C15 C16 . . . . 0.1(4) ?
C14 C15 C16 C17 . . . . 2.6(4) ?
C15 C16 C17 C18 . . . . -1.9(4) ?
C16 C17 C18 C13 . . . . -1.4(4) ?
C16 C17 C18 C19 . . . . 177.6(2) ?
C14 C13 C18 C17 . . . . 4.1(4) ?
C6 C13 C18 C17 . . . . -174.4(2) ?
C14 C13 C18 C19 . . . . -175.1(2) ?
C6 C13 C18 C19 . . . . 6.5(3) ?
C20 N1 C19 C18 . . . . 164.2(2) ?
C6 N1 C19 C18 . . . . -14.2(3) ?
C17 C18 C19 N1 . . . . -174.5(2) ?
C13 C18 C19 N1 . . . . 4.6(3) ?
C19 N1 C20 C21 . . . . 178.9(2) ?
C6 N1 C20 C21 . . . . -2.9(4) ?
N1 C20 C21 N2 . . . . -175.8(2) ?
N1 C20 C21 C22 . . . . -0.3(4) ?
O4 N2 C21 C20 . . . . -6.8(4) ?
O3 N2 C21 C20 . . . . 172.8(2) ?
O4 N2 C21 C22 . . . . 177.8(2) ?
O3 N2 C21 C22 . . . . -2.6(4) ?
C20 C21 C22 C25 . . . . -71.8(3) ?
N2 C21 C22 C25 . . . . 103.6(3) ?
C20 C21 C22 C7 . . . . 38.2(3) ?
N2 C21 C22 C7 . . . . -146.4(2) ?
C8 C7 C22 C21 . . . . 57.5(3) ?
C6 C7 C22 C21 . . . . -67.7(2) ?
C8 C7 C22 C25 . . . . 175.1(2) ?
C6 C7 C22 C25 . . . . 49.9(2) ?
C10 C9 C23 C24 . . . . 1.2(4) ?
C8 C9 C23 C24 . . . . -177.2(2) ?
C9 C23 C24 C12 . . . . 1.2(4) ?
C11 C12 C24 C23 . . . . -2.1(4) ?
C21 C22 C25 C5 . . . . 80.0(2) ?
C7 C22 C25 C5 . . . . -32.9(2) ?
C4 C5 C25 C22 . . . . 126.6(2) ?
C6 C5 C25 C22 . . . . 3.8(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C7 H11 O4 4_665 1.00 2.55 3.497(3) 156.9 ?
C19 H10 O3 6_755 0.99 2.35 3.245(3) 149.3 ?



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

data_zzy1062
_database_code_depnum_ccdc_archive 'CCDC 2071230'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H23 N3 O5'
_chemical_formula_sum            'C26 H23 N3 O5'
_chemical_formula_weight         457.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6642(4)
_cell_length_b                   18.5733(7)
_cell_length_c                   13.4479(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.324(4)
_cell_angle_gamma                90
_cell_volume                     2263.57(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1769
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.1690
_cell_measurement_theta_min      4.2220
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.238
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  31.00   0.50    8.50    --  -33.50  57.00   0.00  156
  2  ω    -32.00  64.00   0.50    8.50    --   36.47 -77.00 150.00  192
  3  ω    -14.00  18.00   0.50    8.50    --   36.47 -57.00   0.00   64
  4  ω     58.00  97.00   0.50    8.50    --   36.47 178.00 -90.00   78
  5  ω     14.00  72.00   0.50    8.50    --   36.47  37.00 -30.00  116
  6  ω     57.00 110.00   0.50    8.50    --   36.47 178.00   0.00  106
  7  ω     37.00  78.00   0.50    8.50    --   36.47  57.00-180.00   82
  8  ω    -32.00  27.00   0.50    8.50    --   36.47 -77.00-150.00  118
  9  ω     38.00  63.00   0.50    8.50    --   36.47 -77.00-150.00   50
 10  ω     40.00  78.00   0.50   35.00    --  108.00 -94.00 -90.00   76
 11  ω     82.00 176.00   0.50   35.00    --  108.00  30.00-150.00  188
 12  ω     50.00 112.00   0.50   35.00    --  108.00-111.00-150.00  124
 13  ω     48.00 129.00   0.50   35.00    --  108.00 -77.00 -90.00  162
 14  ω    101.00 130.00   0.50   35.00    --  108.00 111.00-120.00   58
 15  ω     63.00 131.00   0.50   35.00    --  108.00 -30.00 150.00  136
 16  ω    106.00 171.00   0.50   35.00    --  108.00  61.00 -60.00  130
 17  ω     79.00 144.00   0.50   35.00    --  108.00 178.00-150.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0416056000
_diffrn_orient_matrix_UB_12      0.0756337000
_diffrn_orient_matrix_UB_13      0.0273016000
_diffrn_orient_matrix_UB_21      0.1399874000
_diffrn_orient_matrix_UB_22      0.0311090000
_diffrn_orient_matrix_UB_23      -0.0138731000
_diffrn_orient_matrix_UB_31      -0.0870440000
_diffrn_orient_matrix_UB_32      0.0138644000
_diffrn_orient_matrix_UB_33      -0.1182468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2516
_reflns_number_total             4038
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1138P)²+0.3704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1907
_refine_ls_wR_factor_ref         0.2181
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N2A-C11A
 1.44 with sigma of 0.02
 C13A-N2A
 1.44 with sigma of 0.02
 C11A-C10
 1.39 with sigma of 0.02
 C14A-N2A
 2.5 with sigma of 0.02
 C13A-C15A
 2.5 with sigma of 0.02
 C13-C14
 1.53 with sigma of 0.02
 C14A-C13A
 1.53 with sigma of 0.02
 N2A-C12
 1.43 with sigma of 0.02
 N2-C11
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C14) = Uanis(C14A)
Uanis(C13) = Uanis(C13A)
Uanis(C11) = Uanis(C11A)
Uanis(N2) = Uanis(N2A)
4. Others
 Sof(H9B)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(H9A)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=FVAR(1)
 Sof(H12A)=Sof(N2A)=Sof(C11A)=Sof(H11A)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=Sof(C16A)=
 Sof(H16A)=Sof(C15A)=Sof(C14A)=1-FVAR(2)
 Sof(H12)=Sof(N2)=Sof(C11)=Sof(H11)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(C19)=Sof(H19)=Sof(C18)=Sof(H18)=Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=
 Sof(C15)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C9(H9A), C9(H9B), C12(H12), C12(H12A)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13A(H13C,H13D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4A), C11(H11), C19(H19), C18(H18),
 C17(H17), C16(H16), C20(H20), C21(H21), C11A(H11A), C19A(H19A), C18A(H18A),
 C17A(H17A), C16A(H16A), C20A(H20A), C21A(H21A)
5.d Fitted hexagon refined as free rotating group:
 C14(C19,C18,C17,C16,C15), C19A(C18A,C17A,C16A,C15A,C14A)
5.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
5.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4372(3) 0.63915(16) 0.5248(2) 0.0866(8) Uani 1 1 d . . . . .
O2 O 0.5347(4) 0.81561(17) 0.1173(3) 0.1064(10) Uani 1 1 d . . . . .
O3 O 0.3951(3) 0.72123(18) 0.1022(2) 0.0898(8) Uani 1 1 d . . . . .
O4 O 0.8361(4) 0.46250(17) 0.4370(3) 0.1042(10) Uani 1 1 d . . . . .
H4 H 0.8335 0.4486 0.3784 0.156 Uiso 1 1 calc GR . . . .
O5 O 0.8021(3) 0.47147(15) 0.2454(3) 0.0998(9) Uani 1 1 d . . . . .
N1 N 0.2260(3) 0.7069(2) 0.4821(2) 0.0842(10) Uani 1 1 d . . . . .
H1 H 0.1809 0.6824 0.5157 0.101 Uiso 1 1 calc R . . . .
N3 N 0.4747(3) 0.76935(18) 0.1566(2) 0.0736(8) Uani 1 1 d . . . . .
C1 C 0.2325(4) 0.8563(2) 0.3172(3) 0.0719(9) Uani 1 1 d . . . . .
H1A H 0.2977 0.8752 0.2868 0.086 Uiso 1 1 calc R . . . .
C2 C 0.0949(5) 0.8880(3) 0.2986(4) 0.0954(13) Uani 1 1 d . . . . .
H2 H 0.0676 0.9281 0.2547 0.115 Uiso 1 1 calc R . . . .
C3 C 0.0003(5) 0.8609(4) 0.3441(4) 0.1104(18) Uani 1 1 d . . . . .
H3 H -0.0902 0.8833 0.3317 0.133 Uiso 1 1 calc R . . . .
C4 C 0.0358(4) 0.8012(3) 0.4080(3) 0.1044(16) Uani 1 1 d . . . . .
H4A H -0.0294 0.7828 0.4386 0.125 Uiso 1 1 calc R . . . .
C5 C 0.1692(4) 0.7695(2) 0.4253(3) 0.0747(10) Uani 1 1 d . . . . .
C6 C 0.2698(3) 0.79633(19) 0.3816(2) 0.0602(8) Uani 1 1 d . . . . .
C7 C 0.4017(3) 0.74648(17) 0.4121(2) 0.0566(7) Uani 1 1 d . . . . .
C8 C 0.3594(4) 0.6891(2) 0.4783(2) 0.0667(8) Uani 1 1 d . . . . .
C9 C 0.4280(3) 0.71405(17) 0.3124(2) 0.0580(7) Uani 1 1 d . . . . .
H9A H 0.3298 0.7055 0.2598 0.070 Uiso 0.808(6) 1 calc R . P A 1
H9B H 0.3399 0.6923 0.2608 0.070 Uiso 0.192(6) 1 calc R . P A 2
C10 C 0.4975(3) 0.77216(18) 0.2662(3) 0.0598(8) Uani 1 1 d D . . . .
C12 C 0.5490(3) 0.78086(18) 0.4842(3) 0.0649(8) Uani 1 1 d D . . . .
H12 H 0.6252 0.7435 0.5078 0.078 Uiso 0.695(17) 1 calc R . P B 1
H12A H 0.6190 0.7413 0.5118 0.078 Uiso 0.305(17) 1 calc R . P B 2
C22 C 0.7078(5) 0.5594(2) 0.3313(4) 0.0863(11) Uani 1 1 d . . . . .
C23 C 0.7624(5) 0.5228(2) 0.4266(4) 0.0944(13) Uani 1 1 d . . . . .
C24 C 0.7467(7) 0.5481(4) 0.5276(4) 0.139(2) Uani 1 1 d . . . . .
H24A H 0.7060 0.5101 0.5573 0.208 Uiso 1 1 calc GR . . . .
H24B H 0.6822 0.5891 0.5135 0.208 Uiso 1 1 calc GR . . . .
H24C H 0.8418 0.5614 0.5769 0.208 Uiso 1 1 calc GR . . . .
C25 C 0.7283(5) 0.5280(2) 0.2406(4) 0.0878(12) Uani 1 1 d . . . . .
C26 C 0.6601(6) 0.5626(3) 0.1319(4) 0.1078(15) Uani 1 1 d . . . . .
H26A H 0.7337 0.5672 0.0994 0.162 Uiso 1 1 calc GR . . . .
H26B H 0.6227 0.6094 0.1395 0.162 Uiso 1 1 calc GR . . . .
H26C H 0.5807 0.5330 0.0882 0.162 Uiso 1 1 calc GR . . . .
N2 N 0.5992(19) 0.8383(5) 0.4291(9) 0.0661(17) Uani 0.695(17) 1 d D . P B 1
C11 C 0.5766(16) 0.8232(5) 0.3281(8) 0.0610(19) Uani 0.695(17) 1 d D . P B 1
H11 H 0.6245 0.8537 0.2958 0.073 Uiso 0.695(17) 1 calc R . P B 1
C13 C 0.6581(13) 0.8999(5) 0.4957(8) 0.077(2) Uani 0.695(17) 1 d D . P B 1
H13A H 0.6205 0.9446 0.4587 0.092 Uiso 0.695(17) 1 calc R . P B 1
H13B H 0.7651 0.9005 0.5201 0.092 Uiso 0.695(17) 1 calc R . P B 1
C14 C 0.6042(11) 0.8885(4) 0.5840(6) 0.0799(17) Uani 0.695(17) 1 d D U P B 1
C19 C 0.6173(9) 0.9346(4) 0.6682(7) 0.092(2) Uani 0.695(17) 1 d G U P B 1
H19 H 0.6604 0.9797 0.6710 0.110 Uiso 0.695(17) 1 calc R . P B 1
C18 C 0.5658(9) 0.9134(5) 0.7482(6) 0.099(3) Uani 0.695(17) 1 d G U P B 1
H18 H 0.5746 0.9442 0.8046 0.119 Uiso 0.695(17) 1 calc R . P B 1
C17 C 0.5013(9) 0.8460(5) 0.7441(5) 0.089(2) Uani 0.695(17) 1 d G U P B 1
H17 H 0.4669 0.8318 0.7976 0.106 Uiso 0.695(17) 1 calc R . P B 1
C16 C 0.4882(10) 0.7999(4) 0.6599(5) 0.0735(16) Uani 0.695(17) 1 d G U P B 1
H16 H 0.4450 0.7549 0.6571 0.088 Uiso 0.695(17) 1 calc R . P B 1
C15 C 0.5397(11) 0.8212(4) 0.5798(5) 0.0654(15) Uani 0.695(17) 1 d G U P B 1
C20 C 0.5065(5) 0.6428(2) 0.3289(3) 0.0573(10) Uani 0.808(6) 1 d . . P A 1
H20 H 0.4588 0.6035 0.3454 0.069 Uiso 0.808(6) 1 calc R . P A 1
C21 C 0.6360(5) 0.6315(2) 0.3219(4) 0.0680(11) Uani 0.808(6) 1 d . . P A 1
H21 H 0.6873 0.6711 0.3103 0.082 Uiso 0.808(6) 1 calc R . P A 1
N2A N 0.607(5) 0.8248(12) 0.415(2) 0.0661(17) Uani 0.305(17) 1 d D . P B 2
C11A C 0.568(4) 0.8351(12) 0.308(2) 0.0610(19) Uani 0.305(17) 1 d D . P B 2
H11A H 0.5856 0.8750 0.2718 0.073 Uiso 0.305(17) 1 calc R . P B 2
C13A C 0.663(4) 0.8986(13) 0.4600(17) 0.077(2) Uani 0.305(17) 1 d D . P B 2
H13C H 0.6109 0.9369 0.4126 0.092 Uiso 0.305(17) 1 calc R . P B 2
H13D H 0.7678 0.9034 0.4750 0.092 Uiso 0.305(17) 1 calc R . P B 2
C19A C 0.636(2) 0.9517(8) 0.6371(15) 0.092(2) Uani 0.305(17) 1 d . . P B 2
H19A H 0.6752 0.9964 0.6298 0.110 Uiso 0.305(17) 1 calc R . P B 2
C18A C 0.589(2) 0.9390(9) 0.7222(13) 0.099(3) Uani 0.305(17) 1 d G . P B 2
H18A H 0.5967 0.9751 0.7717 0.119 Uiso 0.305(17) 1 calc R . P B 2
C17A C 0.531(2) 0.8722(10) 0.7332(12) 0.089(2) Uani 0.305(17) 1 d G . P B 2
H17A H 0.4997 0.8637 0.7901 0.106 Uiso 0.305(17) 1 calc R . P B 2
C16A C 0.520(2) 0.8183(9) 0.6592(15) 0.0735(16) Uani 0.305(17) 1 d G . P B 2
H16A H 0.4812 0.7736 0.6666 0.088 Uiso 0.305(17) 1 calc R . P B 2
C15A C 0.567(3) 0.8311(9) 0.5742(15) 0.0654(15) Uani 0.305(17) 1 d DG . P B 2
C14A C 0.625(3) 0.8978(10) 0.5631(14) 0.0799(17) Uani 0.305(17) 1 d DG . P B 2
C20A C 0.578(2) 0.6567(11) 0.3555(17) 0.0573(10) Uani 0.192(6) 1 d . . P A 2
H20A H 0.6662 0.6687 0.4089 0.069 Uiso 0.192(6) 1 calc R . P A 2
C21A C 0.556(2) 0.5954(10) 0.3064(16) 0.0680(11) Uani 0.192(6) 1 d . . P A 2
H21A H 0.4659 0.5766 0.2639 0.082 Uiso 0.192(6) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.221(4) . ?
O2 N3 1.252(4) . ?
O3 N3 1.239(4) . ?
O4 H4 0.8200 . ?
O4 C23 1.309(5) . ?
O5 C25 1.258(5) . ?
N1 H1 0.8600 . ?
N1 C5 1.394(5) . ?
N1 C8 1.349(5) . ?
N3 C10 1.414(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.395(5) . ?
C1 C6 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(8) . ?
C4 H4A 0.9300 . ?
C4 C5 1.361(5) . ?
C5 C6 1.391(5) . ?
C6 C7 1.513(4) . ?
C7 C8 1.533(5) . ?
C7 C9 1.568(4) . ?
C7 C12 1.554(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C10 1.513(4) . ?
C9 C20 1.503(5) . ?
C9 C20A 1.73(2) . ?
C10 C11 1.317(9) . ?
C10 C11A 1.371(19) . ?
C12 H12 0.9800 . ?
C12 H12A 0.9800 . ?
C12 N2 1.474(9) . ?
C12 C15 1.518(6) . ?
C12 N2A 1.487(18) . ?
C12 C15A 1.489(12) . ?
C22 C23 1.384(6) . ?
C22 C25 1.425(6) . ?
C22 C21 1.493(6) . ?
C22 C21A 1.536(19) . ?
C23 C24 1.493(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.522(6) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N2 C11 1.328(9) . ?
N2 C13 1.443(9) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.469(8) . ?
C14 C19 1.3900 . ?
C14 C15 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C20 H20 0.9300 . ?
C20 C21 1.304(7) . ?
C21 H21 0.9300 . ?
N2A C11A 1.370(18) . ?
N2A C13A 1.520(18) . ?
C11A H11A 0.9300 . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A C14A 1.550(14) . ?
C19A H19A 0.9300 . ?
C19A C18A 1.3900 . ?
C19A C14A 1.3900 . ?
C18A H18A 0.9300 . ?
C18A C17A 1.3900 . ?
C17A H17A 0.9300 . ?
C17A C16A 1.3900 . ?
C16A H16A 0.9300 . ?
C16A C15A 1.3900 . ?
C15A C14A 1.3900 . ?
C20A H20A 0.9300 . ?
C20A C21A 1.30(3) . ?
C21A H21A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O4 H4 109.5 . . ?
C5 N1 H1 123.7 . . ?
C8 N1 H1 123.7 . . ?
C8 N1 C5 112.6(3) . . ?
O2 N3 C10 119.2(3) . . ?
O3 N3 O2 122.0(3) . . ?
O3 N3 C10 118.9(3) . . ?
C2 C1 H1A 120.7 . . ?
C6 C1 H1A 120.7 . . ?
C6 C1 C2 118.6(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 H4A 120.9 . . ?
C4 C5 N1 128.5(4) . . ?
C4 C5 C6 122.2(4) . . ?
C6 C5 N1 109.3(3) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 C7 132.5(3) . . ?
C5 C6 C7 108.3(3) . . ?
C6 C7 C8 102.3(3) . . ?
C6 C7 C9 112.0(2) . . ?
C6 C7 C12 114.9(3) . . ?
C8 C7 C9 112.6(3) . . ?
C8 C7 C12 107.1(3) . . ?
C12 C7 C9 107.8(2) . . ?
O1 C8 N1 126.5(3) . . ?
O1 C8 C7 125.8(3) . . ?
N1 C8 C7 107.6(3) . . ?
C7 C9 H9A 106.0 . . ?
C7 C9 H9B 113.8 . . ?
C7 C9 C20A 108.4(7) . . ?
C10 C9 C7 107.7(3) . . ?
C10 C9 H9A 106.0 . . ?
C10 C9 H9B 113.8 . . ?
C10 C9 C20A 97.9(7) . . ?
C20 C9 C7 115.8(3) . . ?
C20 C9 H9A 106.0 . . ?
C20 C9 C10 114.5(3) . . ?
C20A C9 H9B 113.8 . . ?
N3 C10 C9 118.1(3) . . ?
C11 C10 N3 122.1(6) . . ?
C11 C10 C9 119.8(6) . . ?
C11A C10 N3 109.2(12) . . ?
C11A C10 C9 132.2(13) . . ?
C7 C12 H12 109.5 . . ?
C7 C12 H12A 106.9 . . ?
N2 C12 C7 111.9(6) . . ?
N2 C12 H12 109.5 . . ?
N2 C12 C15 101.3(4) . . ?
C15 C12 C7 114.8(4) . . ?
C15 C12 H12 109.5 . . ?
N2A C12 C7 107.1(14) . . ?
N2A C12 H12A 106.9 . . ?
N2A C12 C15A 101.7(11) . . ?
C15A C12 C7 126.0(9) . . ?
C15A C12 H12A 106.9 . . ?
C23 C22 C25 118.1(4) . . ?
C23 C22 C21 122.3(4) . . ?
C23 C22 C21A 116.3(8) . . ?
C25 C22 C21 119.5(4) . . ?
C25 C22 C21A 113.3(8) . . ?
O4 C23 C22 122.4(5) . . ?
O4 C23 C24 113.3(4) . . ?
C22 C23 C24 124.2(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 C22 122.8(4) . . ?
O5 C25 C26 116.7(4) . . ?
C22 C25 C26 120.4(4) . . ?
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 . . ?
C11 N2 C12 113.3(9) . . ?
C11 N2 C13 133.8(9) . . ?
C13 N2 C12 113.0(6) . . ?
C10 C11 N2 130.7(11) . . ?
C10 C11 H11 114.7 . . ?
N2 C11 H11 114.7 . . ?
N2 C13 H13A 111.3 . . ?
N2 C13 H13B 111.3 . . ?
N2 C13 C14 102.3(6) . . ?
H13A C13 H13B 109.2 . . ?
C14 C13 H13A 111.3 . . ?
C14 C13 H13B 111.3 . . ?
C19 C14 C13 127.8(4) . . ?
C19 C14 C15 120.0 . . ?
C15 C14 C13 112.2(4) . . ?
C14 C19 H19 120.0 . . ?
C14 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C14 C15 C12 108.7(4) . . ?
C16 C15 C12 131.2(4) . . ?
C16 C15 C14 120.0 . . ?
C9 C20 H20 117.3 . . ?
C21 C20 C9 125.4(4) . . ?
C21 C20 H20 117.3 . . ?
C22 C21 H21 117.7 . . ?
C20 C21 C22 124.6(4) . . ?
C20 C21 H21 117.7 . . ?
C12 N2A C13A 113.7(13) . . ?
C11A N2A C12 136(3) . . ?
C11A N2A C13A 103.0(18) . . ?
C10 C11A H11A 128.6 . . ?
N2A C11A C10 102.9(19) . . ?
N2A C11A H11A 128.6 . . ?
N2A C13A H13C 111.6 . . ?
N2A C13A H13D 111.6 . . ?
N2A C13A C14A 100.9(11) . . ?
H13C C13A H13D 109.4 . . ?
C14A C13A H13C 111.6 . . ?
C14A C13A H13D 111.6 . . ?
C18A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C17A C18A C19A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C16A C15A C12 125.6(10) . . ?
C16A C15A C14A 120.0 . . ?
C14A C15A C12 114.2(10) . . ?
C19A C14A C13A 130.5(10) . . ?
C15A C14A C13A 109.4(10) . . ?
C15A C14A C19A 120.0 . . ?
C9 C20A H20A 123.1 . . ?
C21A C20A C9 113.7(18) . . ?
C21A C20A H20A 123.1 . . ?
C22 C21A H21A 126.3 . . ?
C20A C21A C22 107.3(18) . . ?
C20A C21A H21A 126.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O5 0.82 1.76 2.486(5) 146.8 .
N1 H1 O2 0.86 2.28 3.039(4) 147.1 4_576
N1 H1 O4 0.86 2.78 3.450(5) 135.5 3_666

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 N3 C10 C9 -177.9(3) . . . . ?
O2 N3 C10 C11 2.0(9) . . . . ?
O2 N3 C10 C11A 9.2(18) . . . . ?
O3 N3 C10 C9 2.5(4) . . . . ?
O3 N3 C10 C11 -177.7(8) . . . . ?
O3 N3 C10 C11A -170.5(18) . . . . ?
N1 C5 C6 C1 176.6(3) . . . . ?
N1 C5 C6 C7 0.5(4) . . . . ?
N3 C10 C11 N2 173.3(15) . . . . ?
N3 C10 C11A N2A -169(3) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C1 C6 C7 C8 -175.5(3) . . . . ?
C1 C6 C7 C9 -54.7(5) . . . . ?
C1 C6 C7 C12 68.8(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C1 C6 C7 175.3(4) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 N1 -176.4(4) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 -177.2(4) . . . . ?
C5 N1 C8 O1 176.3(3) . . . . ?
C5 N1 C8 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C7 C9 120.8(3) . . . . ?
C5 C6 C7 C12 -115.8(3) . . . . ?
C6 C1 C2 C3 0.8(6) . . . . ?
C6 C7 C8 O1 -176.0(3) . . . . ?
C6 C7 C8 N1 -0.3(3) . . . . ?
C6 C7 C9 C10 76.3(3) . . . . ?
C6 C7 C9 C20 -154.0(3) . . . . ?
C6 C7 C9 C20A -178.8(8) . . . . ?
C6 C7 C12 N2 -65.9(6) . . . . ?
C6 C7 C12 C15 48.9(5) . . . . ?
C6 C7 C12 N2A -78.9(13) . . . . ?
C6 C7 C12 C15A 40.2(11) . . . . ?
C7 C9 C10 N3 -153.1(3) . . . . ?
C7 C9 C10 C11 27.1(8) . . . . ?
C7 C9 C10 C11A 18(2) . . . . ?
C7 C9 C20 C21 -115.5(5) . . . . ?
C7 C9 C20A C21A 133.7(15) . . . . ?
C7 C12 N2 C11 -39.0(16) . . . . ?
C7 C12 N2 C13 139.1(11) . . . . ?
C7 C12 C15 C14 -130.8(4) . . . . ?
C7 C12 C15 C16 53.5(8) . . . . ?
C7 C12 N2A C11A -7(5) . . . . ?
C7 C12 N2A C13A 135(3) . . . . ?
C7 C12 C15A C16A 53.7(19) . . . . ?
C7 C12 C15A C14A -120.6(10) . . . . ?
C8 N1 C5 C4 176.7(4) . . . . ?
C8 N1 C5 C6 -0.8(4) . . . . ?
C8 C7 C9 C10 -169.0(3) . . . . ?
C8 C7 C9 C20 -39.3(4) . . . . ?
C8 C7 C9 C20A -64.1(8) . . . . ?
C8 C7 C12 N2 -178.8(6) . . . . ?
C8 C7 C12 C15 -64.0(5) . . . . ?
C8 C7 C12 N2A 168.2(13) . . . . ?
C8 C7 C12 C15A -72.6(11) . . . . ?
C9 C7 C8 O1 63.5(4) . . . . ?
C9 C7 C8 N1 -120.8(3) . . . . ?
C9 C7 C12 N2 59.7(6) . . . . ?
C9 C7 C12 C15 174.5(4) . . . . ?
C9 C7 C12 N2A 46.8(13) . . . . ?
C9 C7 C12 C15A 165.9(11) . . . . ?
C9 C10 C11 N2 -7(2) . . . . ?
C9 C10 C11A N2A 19(4) . . . . ?
C9 C20 C21 C22 -175.6(4) . . . . ?
C9 C20A C21A C22 165.4(11) . . . . ?
C10 C9 C20 C21 10.8(6) . . . . ?
C10 C9 C20A C21A -114.6(16) . . . . ?
C12 C7 C8 O1 -54.8(4) . . . . ?
C12 C7 C8 N1 120.8(3) . . . . ?
C12 C7 C9 C10 -51.1(3) . . . . ?
C12 C7 C9 C20 78.6(4) . . . . ?
C12 C7 C9 C20A 53.9(8) . . . . ?
C12 N2 C11 C10 12(3) . . . . ?
C12 N2 C13 C14 -15.9(16) . . . . ?
C12 N2A C11A C10 -26(6) . . . . ?
C12 N2A C13A C14A -3(4) . . . . ?
C12 C15A C14A C13A -3.0(19) . . . . ?
C12 C15A C14A C19A 174.7(18) . . . . ?
C23 C22 C25 O5 -5.0(7) . . . . ?
C23 C22 C25 C26 175.1(4) . . . . ?
C23 C22 C21 C20 -71.2(7) . . . . ?
C23 C22 C21A C20A 82.2(16) . . . . ?
C25 C22 C23 O4 2.6(7) . . . . ?
C25 C22 C23 C24 -178.7(5) . . . . ?
C25 C22 C21 C20 112.1(6) . . . . ?
C25 C22 C21A C20A -136.0(13) . . . . ?
N2 C12 C15 C14 -9.9(8) . . . . ?
N2 C12 C15 C16 174.3(9) . . . . ?
N2 C13 C14 C19 -174.2(9) . . . . ?
N2 C13 C14 C15 8.8(12) . . . . ?
C11 N2 C13 C14 161.7(19) . . . . ?
C13 N2 C11 C10 -165.3(14) . . . . ?
C13 C14 C19 C18 -176.7(11) . . . . ?
C13 C14 C15 C12 0.9(7) . . . . ?
C13 C14 C15 C16 177.2(9) . . . . ?
C14 C19 C18 C17 0.0 . . . . ?
C19 C14 C15 C12 -176.3(7) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C19 C18 C17 C16 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C17 C16 C15 C12 175.4(9) . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C15 C12 N2 C11 -161.8(13) . . . . ?
C15 C12 N2 C13 16.3(14) . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C20 C9 C10 N3 76.5(4) . . . . ?
C20 C9 C10 C11 -103.3(8) . . . . ?
C21 C22 C23 O4 -174.2(4) . . . . ?
C21 C22 C23 C24 4.5(8) . . . . ?
C21 C22 C25 O5 171.9(4) . . . . ?
C21 C22 C25 C26 -8.0(6) . . . . ?
N2A C12 C15A C16A 175(2) . . . . ?
N2A C12 C15A C14A 1(2) . . . . ?
N2A C13A C14A C19A -174(2) . . . . ?
N2A C13A C14A C15A 4(3) . . . . ?
C11A N2A C13A C14A 151(3) . . . . ?
C13A N2A C11A C10 -171(3) . . . . ?
C19A C18A C17A C16A 0.0 . . . . ?
C18A C19A C14A C13A 177(3) . . . . ?
C18A C19A C14A C15A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C17A C16A C15A C12 -174(2) . . . . ?
C17A C16A C15A C14A 0.0 . . . . ?
C16A C15A C14A C13A -178(2) . . . . ?
C16A C15A C14A C19A 0.0 . . . . ?
C15A C12 N2A C11A -141(4) . . . . ?
C15A C12 N2A C13A 2(4) . . . . ?
C14A C19A C18A C17A 0.0 . . . . ?
C20A C9 C10 N3 94.6(8) . . . . ?
C20A C9 C10 C11A -94(2) . . . . ?
C21A C22 C23 O4 142.5(9) . . . . ?
C21A C22 C23 C24 -38.8(11) . . . . ?
C21A C22 C25 O5 -146.0(9) . . . . ?
C21A C22 C25 C26 34.1(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.840
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2086417'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2 O4, C H4 O'
_chemical_formula_sum            'C22 H22 N2 O5'
_chemical_formula_weight         394.41
_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5481(2)
_cell_length_b                   11.4787(3)
_cell_length_c                   12.3488(4)
_cell_angle_alpha                64.2362(13)
_cell_angle_beta                 78.0893(13)
_cell_angle_gamma                87.4663(15)
_cell_volume                     941.57(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7405
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      4.06
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1259 before and 0.0793 after correction. The Ratio of minimum to maximum transmission is 0.7294. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11740
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.437
_diffrn_reflns_theta_min         4.064
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3000
_reflns_number_total             3432
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.053
_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)+(0.0955P)²+0.2495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1564
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H2 of C2, H3 of C3, H1A of C1, H9 of C9, H4 of C4, H12
  of C12, H13 of C13, H10 of C10, H18 of C18, H17 of C17, H21 of C21, H19 of
  C19, H20 of C20
 At 1.5 times of:
  All C(H,H,H) groups, H5 of C21, All C(H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O5A-C22A
 1.43 with sigma of 0.02
 H1-O1
 0.9 with sigma of 0.02
 O5-C22
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5) = Uanis(O5A)
Uanis(C22) = Uanis(C22A)
4. Others
 Sof(O5A)=Sof(H5A)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(H5)=Sof(O5)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C12(H12), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
5.e Idealised tetrahedral OH refined as rotating group:
 O5A(H5A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.04314(16) 0.59253(13) 0.53904(11) 0.0322(3) Uani 1 1 d D . . . .
O2 O 0.47969(17) 0.37830(14) 0.89071(13) 0.0383(3) Uani 1 1 d . . . . .
O3 O 0.99676(18) 0.18728(13) 1.07214(12) 0.0375(3) Uani 1 1 d . . . . .
O4 O 0.87299(19) 0.31378(14) 1.15358(11) 0.0382(3) Uani 1 1 d . . . . .
N1 N 0.76008(19) 0.56708(14) 0.83166(12) 0.0269(3) Uani 1 1 d . . . . .
N2 N 0.91801(18) 0.28892(14) 1.06262(13) 0.0285(3) Uani 1 1 d . . . . .
C1 C 0.4769(3) 0.7976(2) 0.63468(18) 0.0426(5) Uani 1 1 d . . . . .
H1A H 0.4273 0.8581 0.6647 0.051 Uiso 1 1 calc R . . . .
C2 C 0.4321(3) 0.7973(2) 0.53196(19) 0.0488(5) Uani 1 1 d . . . . .
H2 H 0.3516 0.8586 0.4906 0.059 Uiso 1 1 calc R . . . .
C3 C 0.5038(3) 0.7080(2) 0.48820(19) 0.0465(5) Uani 1 1 d . . . . .
H3 H 0.4696 0.7077 0.4185 0.056 Uiso 1 1 calc R . . . .
C4 C 0.6246(3) 0.6198(2) 0.54555(17) 0.0377(4) Uani 1 1 d . . . . .
H4 H 0.6743 0.5593 0.5156 0.045 Uiso 1 1 calc R . . . .
C5 C 0.6714(2) 0.62178(18) 0.64747(15) 0.0305(4) Uani 1 1 d . . . . .
C6 C 0.5956(2) 0.70806(18) 0.69345(16) 0.0335(4) Uani 1 1 d . . . . .
C7 C 0.6558(3) 0.68371(18) 0.80958(17) 0.0361(4) Uani 1 1 d . . . . .
H7A H 0.7327 0.7575 0.7982 0.043 Uiso 1 1 calc R . . . .
H7B H 0.5508 0.6677 0.8782 0.043 Uiso 1 1 calc R . . . .
C8 C 0.7964(2) 0.53601(16) 0.72419(14) 0.0260(4) Uani 1 1 d . . . . .
C9 C 0.7737(2) 0.38961(16) 0.76805(14) 0.0256(4) Uani 1 1 d . . . . .
H9 H 0.8062 0.3717 0.6942 0.031 Uiso 1 1 calc R . . . .
C10 C 0.9299(2) 0.34408(17) 0.84002(15) 0.0271(4) Uani 1 1 d . . . . .
H10 H 0.9525 0.2504 0.8642 0.033 Uiso 1 1 calc R . . . .
C11 C 0.8809(2) 0.37376(16) 0.94941(15) 0.0260(4) Uani 1 1 d . . . . .
C12 C 0.7976(2) 0.48681(17) 0.93787(14) 0.0266(4) Uani 1 1 d . . . . .
H12 H 0.7676 0.5066 1.0064 0.032 Uiso 1 1 calc R . . . .
C13 C 1.0047(2) 0.56202(17) 0.66622(15) 0.0282(4) Uani 1 1 d . . . . .
H13 H 1.0522 0.6346 0.6782 0.034 Uiso 1 1 calc R . . . .
C14 C 1.0896(2) 0.43431(18) 0.74213(15) 0.0307(4) Uani 1 1 d . . . . .
H14A H 1.1504 0.3944 0.6885 0.037 Uiso 1 1 calc R . . . .
H14B H 1.1798 0.4511 0.7822 0.037 Uiso 1 1 calc R . . . .
C15 C 0.5862(2) 0.32742(17) 0.83791(15) 0.0277(4) Uani 1 1 d . . . . .
C16 C 0.5360(2) 0.20245(17) 0.83975(14) 0.0276(4) Uani 1 1 d . . . . .
C17 C 0.3589(2) 0.15093(18) 0.89476(16) 0.0336(4) Uani 1 1 d . . . . .
H17 H 0.2753 0.1948 0.9309 0.040 Uiso 1 1 calc R . . . .
C18 C 0.3041(3) 0.0362(2) 0.89704(19) 0.0410(5) Uani 1 1 d . . . . .
H18 H 0.1828 0.0023 0.9337 0.049 Uiso 1 1 calc R . . . .
C19 C 0.4260(3) -0.02908(19) 0.84584(18) 0.0410(5) Uani 1 1 d . . . . .
H19 H 0.3882 -0.1080 0.8479 0.049 Uiso 1 1 calc R . . . .
C20 C 0.6021(3) 0.02017(19) 0.79194(18) 0.0386(4) Uani 1 1 d . . . . .
H20 H 0.6856 -0.0250 0.7573 0.046 Uiso 1 1 calc R . . . .
C21 C 0.6573(2) 0.13565(18) 0.78840(16) 0.0326(4) Uani 1 1 d . . . . .
H21 H 0.7785 0.1695 0.7508 0.039 Uiso 1 1 calc R . . . .
H5 H 0.053(7) 0.849(5) 0.712(5) 0.049 Uiso 0.486(3) 1 d R . P . .
O5 O 0.0111(4) 0.9115(3) 0.6424(3) 0.0454(5) Uani 0.486(3) 1 d D . P A 1
O5A O -0.0219(4) 0.1428(3) 0.5539(3) 0.0454(5) Uani 0.514(3) 1 d D . P A 2
H5A H -0.0286 0.1260 0.4951 0.068 Uiso 0.514(3) 1 calc GR . P A 2
C22 C 0.079(4) 1.0370(17) 0.623(4) 0.066(2) Uani 0.486(3) 1 d D . P A 1
H22A H 0.0127 1.1052 0.5680 0.098 Uiso 0.486(3) 1 calc GR . P A 1
H22B H 0.2082 1.0491 0.5848 0.098 Uiso 0.486(3) 1 calc GR . P A 1
H22C H 0.0607 1.0415 0.7015 0.098 Uiso 0.486(3) 1 calc GR . P A 1
C22A C 0.100(4) 0.0602(17) 0.622(3) 0.066(2) Uani 0.514(3) 1 d D . P A 2
H22D H 0.2014 0.0467 0.5654 0.098 Uiso 0.514(3) 1 calc GR . P A 2
H22E H 0.0367 -0.0233 0.6796 0.098 Uiso 0.514(3) 1 calc GR . P A 2
H22F H 0.1455 0.0999 0.6673 0.098 Uiso 0.514(3) 1 calc GR . P A 2
H1 H 1.022(5) 0.678(2) 0.503(3) 0.098 Uiso 1 1 d DR . . . .


_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 C13 1.420(2) . ?
O1 H1 0.906(19) . ?
O2 C15 1.219(2) . ?
O3 N2 1.256(2) . ?
O4 N2 1.253(2) . ?
N1 C7 1.471(2) . ?
N1 C8 1.4888(19) . ?
N1 C12 1.315(2) . ?
N2 C11 1.391(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.380(3) . ?
C1 C6 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 C6 1.391(3) . ?
C5 C8 1.494(2) . ?
C6 C7 1.500(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.531(2) . ?
C8 C13 1.570(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.558(2) . ?
C9 C15 1.519(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.503(2) . ?
C10 C14 1.552(2) . ?
C11 C12 1.380(2) . ?
C12 H12 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.552(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.489(2) . ?
C16 C17 1.394(3) . ?
C16 C21 1.396(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9500 . ?
O5 H5 0.96(6) . ?
O5 C22 1.449(18) . ?
O5A H5A 0.8400 . ?
O5A C22A 1.412(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 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
C13 O1 H1 103(2) . . ?
C7 N1 C8 112.34(13) . . ?
C12 N1 C7 125.45(14) . . ?
C12 N1 C8 121.58(14) . . ?
O3 N2 C11 118.99(14) . . ?
O4 N2 O3 120.69(15) . . ?
O4 N2 C11 120.32(15) . . ?
C2 C1 H1A 120.6 . . ?
C2 C1 C6 118.90(19) . . ?
C6 C1 H1A 120.6 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.68(19) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.55(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.55(19) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 120.93(17) . . ?
C4 C5 C8 127.98(17) . . ?
C6 C5 C8 111.06(15) . . ?
C1 C6 C5 120.34(18) . . ?
C1 C6 C7 128.94(17) . . ?
C5 C6 C7 110.68(16) . . ?
N1 C7 C6 102.49(14) . . ?
N1 C7 H7A 111.3 . . ?
N1 C7 H7B 111.3 . . ?
C6 C7 H7A 111.3 . . ?
C6 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N1 C8 C5 101.89(13) . . ?
N1 C8 C9 109.99(13) . . ?
N1 C8 C13 107.96(13) . . ?
C5 C8 C9 118.51(14) . . ?
C5 C8 C13 116.66(14) . . ?
C9 C8 C13 101.61(13) . . ?
C8 C9 H9 107.9 . . ?
C8 C9 C10 99.71(13) . . ?
C10 C9 H9 107.9 . . ?
C15 C9 C8 116.38(14) . . ?
C15 C9 H9 107.9 . . ?
C15 C9 C10 116.46(13) . . ?
C9 C10 H10 112.2 . . ?
C11 C10 C9 107.36(13) . . ?
C11 C10 H10 112.2 . . ?
C11 C10 C14 111.81(14) . . ?
C14 C10 C9 100.33(13) . . ?
C14 C10 H10 112.2 . . ?
N2 C11 C10 121.09(15) . . ?
C12 C11 N2 119.21(15) . . ?
C12 C11 C10 119.70(15) . . ?
N1 C12 C11 119.76(15) . . ?
N1 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O1 C13 C8 112.35(13) . . ?
O1 C13 H13 109.5 . . ?
O1 C13 C14 111.75(13) . . ?
C8 C13 H13 109.5 . . ?
C14 C13 C8 104.08(13) . . ?
C14 C13 H13 109.5 . . ?
C10 C14 C13 105.96(13) . . ?
C10 C14 H14A 110.5 . . ?
C10 C14 H14B 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
O2 C15 C9 121.07(15) . . ?
O2 C15 C16 120.90(15) . . ?
C16 C15 C9 118.03(14) . . ?
C17 C16 C15 118.05(15) . . ?
C17 C16 C21 118.89(17) . . ?
C21 C16 C15 123.06(15) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.43(17) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.06(18) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.18(18) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.01(18) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.44(17) . . ?
C20 C21 H21 119.8 . . ?
C22 O5 H5 106(3) . . ?
C22A O5A H5A 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5A C22A H22D 109.5 . . ?
O5A C22A H22E 109.5 . . ?
O5A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O3 0.96(6) 2.46(6) 3.187(3) 133(4) 2_667
O5 H5 O4 0.96(6) 2.04(6) 2.974(3) 167(5) 2_667
O5 H5 N2 0.96(6) 2.59(6) 3.501(3) 160(4) 2_667
O1 H1 O5A 0.906(19) 1.86(2) 2.752(3) 167(4) 2_666

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C10 -122.74(14) . . . . ?
O2 C15 C16 C17 5.2(2) . . . . ?
O2 C15 C16 C21 -175.22(16) . . . . ?
O3 N2 C11 C10 1.3(2) . . . . ?
O3 N2 C11 C12 -178.72(14) . . . . ?
O4 N2 C11 C10 -178.53(14) . . . . ?
O4 N2 C11 C12 1.4(2) . . . . ?
N1 C8 C9 C10 -64.12(15) . . . . ?
N1 C8 C9 C15 62.00(17) . . . . ?
N1 C8 C13 O1 -153.46(14) . . . . ?
N1 C8 C13 C14 85.45(15) . . . . ?
N2 C11 C12 N1 -179.25(14) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C1 C6 C7 N1 172.7(2) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -175.9(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C3 C4 C5 C8 179.37(18) . . . . ?
C4 C5 C6 C1 -2.6(3) . . . . ?
C4 C5 C6 C7 175.29(17) . . . . ?
C4 C5 C8 N1 -168.67(18) . . . . ?
C4 C5 C8 C9 -47.9(2) . . . . ?
C4 C5 C8 C13 74.1(2) . . . . ?
C5 C6 C7 N1 -5.0(2) . . . . ?
C5 C8 C9 C10 179.33(13) . . . . ?
C5 C8 C9 C15 -54.55(19) . . . . ?
C5 C8 C13 O1 -39.6(2) . . . . ?
C5 C8 C13 C14 -160.65(14) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C5 C8 N1 9.29(18) . . . . ?
C6 C5 C8 C9 130.08(16) . . . . ?
C6 C5 C8 C13 -107.98(17) . . . . ?
C7 N1 C8 C5 -12.83(18) . . . . ?
C7 N1 C8 C9 -139.39(15) . . . . ?
C7 N1 C8 C13 110.55(16) . . . . ?
C7 N1 C12 C11 173.46(16) . . . . ?
C8 N1 C7 C6 11.33(19) . . . . ?
C8 N1 C12 C11 3.3(2) . . . . ?
C8 C5 C6 C1 179.24(17) . . . . ?
C8 C5 C6 C7 -2.8(2) . . . . ?
C8 C9 C10 C11 66.47(15) . . . . ?
C8 C9 C10 C14 -50.44(14) . . . . ?
C8 C9 C15 O2 -23.3(2) . . . . ?
C8 C9 C15 C16 156.52(14) . . . . ?
C8 C13 C14 C10 -1.26(16) . . . . ?
C9 C8 C13 O1 90.85(15) . . . . ?
C9 C8 C13 C14 -30.23(15) . . . . ?
C9 C10 C11 N2 141.60(15) . . . . ?
C9 C10 C11 C12 -38.3(2) . . . . ?
C9 C10 C14 C13 31.54(16) . . . . ?
C9 C15 C16 C17 -174.59(15) . . . . ?
C9 C15 C16 C21 5.0(2) . . . . ?
C10 C9 C15 O2 93.9(2) . . . . ?
C10 C9 C15 C16 -86.27(18) . . . . ?
C10 C11 C12 N1 0.7(2) . . . . ?
C11 C10 C14 C13 -82.01(16) . . . . ?
C12 N1 C7 C6 -159.64(16) . . . . ?
C12 N1 C8 C5 158.54(15) . . . . ?
C12 N1 C8 C9 32.0(2) . . . . ?
C12 N1 C8 C13 -78.08(18) . . . . ?
C13 C8 C9 C10 50.07(14) . . . . ?
C13 C8 C9 C15 176.19(13) . . . . ?
C14 C10 C11 N2 -109.28(17) . . . . ?
C14 C10 C11 C12 70.77(19) . . . . ?
C15 C9 C10 C11 -59.60(18) . . . . ?
C15 C9 C10 C14 -176.51(14) . . . . ?
C15 C16 C17 C18 178.83(16) . . . . ?
C15 C16 C21 C20 -179.40(16) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C16 0.4(3) . . . . ?
C21 C16 C17 C18 -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_wll149_sq
_database_code_depnum_ccdc_archive 'CCDC 2071233'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2020-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C26 H22 N2 O5)'
_chemical_formula_sum            'C26 H22 N2 O5'
_chemical_formula_weight         442.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4
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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5554(4)
_cell_length_b                   11.9041(4)
_cell_length_c                   20.6216(6)
_cell_angle_alpha                82.000(3)
_cell_angle_beta                 89.792(3)
_cell_angle_gamma                61.583(4)
_cell_volume                     2464.17(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6170
_cell_measurement_theta_min      4.2670
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.275
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -18.00   0.50    1.50    --  -33.50 -57.00-180.00  168
  2  ω    -55.00 -29.00   0.50    1.50    --  -33.50  77.00  30.00   52
  3  ω     -7.00  25.00   0.50    1.50    --  -33.50  77.00  30.00   64
  4  ω    -59.00 -33.00   0.50    1.50    --  -33.50 -57.00 -90.00   52
  5  ω    -58.00 -32.00   0.50    1.50    --  -33.50 178.00 120.00   52
  6  ω     82.00 107.00   0.50    1.50    --   36.47  37.00 -30.00   50
  7  ω      2.00  33.00   0.50    1.50    --   36.47 -99.00-120.00   62
  8  ω      9.00  98.00   0.50    1.50    --   36.47  77.00 120.00  178
  9  ω     14.00  78.00   0.50    1.50    --   36.47  37.00 -30.00  128
 10  ω     45.00  75.00   0.50    1.50    --   36.47 -99.00-120.00   60
 11  ω     15.00  41.00   0.50    1.50    --   36.47  37.00  90.00   52
 12  ω     19.00  47.00   0.50    1.50    --   36.47  57.00 150.00   56
 13  ω     49.00  75.00   0.50    1.50    --   36.47  37.00  90.00   52
 14  ω    -27.00  63.00   0.50    1.50    --   36.47 -77.00   0.00  180
 15  ω     50.00  77.00   0.50    1.50    --   36.47 -99.00 -90.00   54
 16  ω     10.00  42.00   0.50    1.50    --   36.47 -99.00 -90.00   64
 17  ω     72.00 109.00   0.50    1.50    --   36.47 178.00-120.00   74
 18  ω    -35.00  21.00   0.50    1.50    --   36.47 -19.00-150.00  112
 19  ω     75.00 101.00   0.50    1.50    --   36.47  57.00 150.00   52
 20  ω     80.00 105.00   0.50    7.50    --  108.00 -94.00 -60.00   50
 21  ω     89.00 168.00   0.50    7.50    --  108.00  61.00 150.00  158
 22  ω     89.00 115.00   0.50    7.50    --  108.00  77.00 -30.00   52
 23  ω     85.00 130.00   0.50    7.50    --  108.00 -77.00  60.00   90
 24  ω     43.00 111.00   0.50    7.50    --  108.00-111.00-120.00  136
 25  ω    133.00 175.00   0.50    7.50    --  108.00  30.00-180.00   84
 26  ω     41.00 128.00   0.50    7.50    --  108.00 -45.00   0.00  174
 27  ω     82.00 108.00   0.50    7.50    --  108.00  30.00-180.00   52
 28  ω     39.00 127.00   0.50    7.50    --  108.00 -45.00-180.00  176
 29  ω     55.00 109.00   0.50    7.50    --  108.00 -94.00  90.00  108
 30  ω    105.00 131.00   0.50    7.50    --  108.00 111.00-150.00   52
 31  ω     64.00 119.00   0.50    7.50    --  108.00 178.00  60.00  110
 32  ω     73.00 123.00   0.50    7.50    --  108.00 -45.00  90.00  100
 33  ω     38.00 112.00   0.50    7.50    --  108.00-111.00  60.00  148
 34  ω     64.00 178.00   0.50    7.50    --  108.00   0.00 120.00  228
 35  ω     63.00 137.00   0.50    7.50    --  108.00 -77.00-120.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0659802000
_diffrn_orient_matrix_UB_12      0.0556547000
_diffrn_orient_matrix_UB_13      0.0409196000
_diffrn_orient_matrix_UB_21      -0.1329452000
_diffrn_orient_matrix_UB_22      0.1242534000
_diffrn_orient_matrix_UB_23      -0.0015494000
_diffrn_orient_matrix_UB_31      -0.0327024000
_diffrn_orient_matrix_UB_32      -0.0604757000
_diffrn_orient_matrix_UB_33      0.0635926000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6803
_reflns_number_total             8791
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     606
_refine_ls_number_reflns         8791
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.035
_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)+(0.0852P)²+0.3079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1574
_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. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
Uanis(C26) = Uanis(C26A)
Uanis(C21) = Uanis(C21A)
3. Others
 Sof(C21A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=
 Sof(C23A)=Sof(H23A)=Sof(C22A)=Sof(H22A)=1-FVAR(1)
 Sof(C21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=
 Sof(H25)=Sof(C26)=Sof(H26)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C8'(H8'), C9'(H9'), C10'(H10')
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7'(H7'A,H7'B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C14(H14), C26A(H26A), C25A(H25A),
 C24A(H24A), C23A(H23A), C22A(H22A), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26), C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C12'(H12'), C14'(H14'),
 C22'(H22'), C23'(H23'), C24'(H24'), C25'(H25'), C26'(H26')
4.d Fitted hexagon refined as free rotating group:
 C21A(C26A,C25A,C24A,C23A,C22A)
4.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C17'(H17D,H17E,H17F), C19'(H19D,
 H19E,H19F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.67898(17) 0.32221(16) 0.04745(8) 0.0639(4) Uani 1 1 d . . . . .
O2 O 0.68604(18) 0.49325(19) 0.06685(9) 0.0717(5) Uani 1 1 d . . . . .
O3 O 0.51418(16) 0.69678(15) 0.19450(7) 0.0552(4) Uani 1 1 d . . . . .
O4 O 0.6502(2) 0.3684(2) 0.36442(10) 0.0896(6) Uani 1 1 d . . . . .
O5 O 0.21684(19) 0.77285(15) 0.20304(7) 0.0639(4) Uani 1 1 d . . . . .
N1 N 0.31217(16) 0.45244(15) 0.10442(8) 0.0441(4) Uani 1 1 d . . . . .
N2 N 0.62783(18) 0.42887(18) 0.06695(8) 0.0524(4) Uani 1 1 d . . . . .
C1 C 0.0039(2) 0.6895(2) 0.16363(12) 0.0593(5) Uani 1 1 d . . . . .
H1 H 0.0156 0.7445 0.1875 0.071 Uiso 1 1 calc R . . . .
C2 C -0.1195(3) 0.7005(3) 0.15389(15) 0.0737(7) Uani 1 1 d . . . . .
H2 H -0.1914 0.7645 0.1710 0.088 Uiso 1 1 calc R . . . .
C3 C -0.1385(3) 0.6185(3) 0.11940(14) 0.0696(7) Uani 1 1 d . . . . .
H3 H -0.2226 0.6280 0.1132 0.084 Uiso 1 1 calc R . . . .
C4 C -0.0328(2) 0.5224(2) 0.09404(12) 0.0601(6) Uani 1 1 d . . . . .
H4 H -0.0444 0.4662 0.0710 0.072 Uiso 1 1 calc R . . . .
C5 C 0.0907(2) 0.5115(2) 0.10357(10) 0.0484(4) Uani 1 1 d . . . . .
C6 C 0.1098(2) 0.59492(19) 0.13718(9) 0.0454(4) Uani 1 1 d . . . . .
C7 C 0.2198(2) 0.4099(2) 0.08444(12) 0.0561(5) Uani 1 1 d . . . . .
H7A H 0.2420 0.3247 0.1077 0.067 Uiso 1 1 calc R . . . .
H7B H 0.2180 0.4084 0.0376 0.067 Uiso 1 1 calc R . . . .
C8 C 0.25286(19) 0.56140(17) 0.14203(9) 0.0407(4) Uani 1 1 d . . . . .
H8 H 0.2881 0.5315 0.1879 0.049 Uiso 1 1 calc R . . . .
C9 C 0.28917(19) 0.66462(17) 0.11092(9) 0.0416(4) Uani 1 1 d . . . . .
H9 H 0.2562 0.6900 0.0646 0.050 Uiso 1 1 calc R . . . .
C10 C 0.4429(2) 0.60635(19) 0.11411(9) 0.0446(4) Uani 1 1 d . . . . .
H10 H 0.4634 0.6649 0.0841 0.054 Uiso 1 1 calc R . . . .
C11 C 0.5000(2) 0.47942(19) 0.08897(9) 0.0441(4) Uani 1 1 d . . . . .
C12 C 0.4298(2) 0.41650(18) 0.08160(9) 0.0446(4) Uani 1 1 d . . . . .
H12 H 0.4659 0.3454 0.0596 0.054 Uiso 1 1 calc R . . . .
C13 C 0.5038(2) 0.5913(2) 0.18111(10) 0.0476(4) Uani 1 1 d . . . . .
C14 C 0.5500(2) 0.4986(2) 0.23309(10) 0.0510(5) Uani 1 1 d . . . . .
H14 H 0.5548 0.4178 0.2362 0.061 Uiso 1 1 calc R . . . .
C15 C 0.5913(2) 0.5469(2) 0.28403(10) 0.0538(5) Uani 1 1 d . . . . .
C16 C 0.5677(2) 0.6678(2) 0.25760(11) 0.0564(5) Uani 1 1 d . . . . .
C17 C 0.5819(4) 0.7757(3) 0.27956(15) 0.0856(9) Uani 1 1 d . . . . .
H17A H 0.6733 0.7471 0.2905 0.128 Uiso 1 1 calc GR . . . .
H17B H 0.5328 0.8008 0.3174 0.128 Uiso 1 1 calc GR . . . .
H17C H 0.5486 0.8482 0.2448 0.128 Uiso 1 1 calc GR . . . .
C18 C 0.6423(2) 0.4737(3) 0.35018(12) 0.0637(6) Uani 1 1 d . . . . .
C19 C 0.6801(4) 0.5327(4) 0.40068(15) 0.0949(10) Uani 1 1 d . . . . .
H19A H 0.6957 0.4807 0.4430 0.142 Uiso 1 1 calc GR . . . .
H19B H 0.6099 0.6185 0.4021 0.142 Uiso 1 1 calc GR . . . .
H19C H 0.7589 0.5365 0.3892 0.142 Uiso 1 1 calc GR . . . .
C20 C 0.2251(2) 0.78473(19) 0.14428(9) 0.0441(4) Uani 1 1 d . . . . .
C21 C 0.1736(17) 0.9061(11) 0.1074(9) 0.0466(6) Uani 0.268(10) 1 d . . P A 1
C21A C 0.1709(5) 0.9182(3) 0.1023(3) 0.0466(6) Uani 0.732(10) 1 d . . P A 2
C26A C 0.1907(7) 0.9358(5) 0.0359(3) 0.0589(16) Uani 0.732(10) 1 d G . P A 2
H26A H 0.2433 0.8648 0.0157 0.071 Uiso 0.732(10) 1 calc R . P A 2
C25A C 0.1318(7) 1.0596(6) -0.00023(19) 0.0859(11) Uani 0.732(10) 1 d G . P A 2
H25A H 0.1450 1.0713 -0.0446 0.103 Uiso 0.732(10) 1 calc R . P A 2
C24A C 0.0531(6) 1.1657(4) 0.02997(18) 0.0859(17) Uani 0.732(10) 1 d G . P A 2
H24A H 0.0137 1.2485 0.0058 0.103 Uiso 0.732(10) 1 calc R . P A 2
C23A C 0.0333(7) 1.1481(3) 0.0963(2) 0.0910(19) Uani 0.732(10) 1 d G . P A 2
H23A H -0.0194 1.2191 0.1165 0.109 Uiso 0.732(10) 1 calc R . P A 2
C22A C 0.0922(5) 1.0244(3) 0.13248(19) 0.0658(12) Uani 0.732(10) 1 d G . P A 2
H22A H 0.0789 1.0126 0.1769 0.079 Uiso 0.732(10) 1 calc R . P A 2
C22 C 0.1465(15) 1.0119(13) 0.1410(7) 0.0658(12) Uani 0.268(10) 1 d . . P A 1
H22 H 0.1565 0.9988 0.1866 0.079 Uiso 0.268(10) 1 calc R . P A 1
C23 C 0.1047(19) 1.1354(12) 0.1055(8) 0.0910(19) Uani 0.268(10) 1 d . . P A 1
H23 H 0.0777 1.2054 0.1280 0.109 Uiso 0.268(10) 1 calc R . P A 1
C24 C 0.1029(18) 1.1543(16) 0.0414(8) 0.0859(17) Uani 0.268(10) 1 d . . P A 1
H24 H 0.0800 1.2360 0.0187 0.103 Uiso 0.268(10) 1 calc R . P A 1
C25 C 0.134(2) 1.057(2) 0.0095(9) 0.0859(11) Uani 0.268(10) 1 d . . P A 1
H25 H 0.1334 1.0718 -0.0360 0.103 Uiso 0.268(10) 1 calc R . P A 1
C26 C 0.166(3) 0.9334(17) 0.0403(10) 0.0589(16) Uani 0.268(10) 1 d . . P A 1
H26 H 0.1829 0.8687 0.0152 0.071 Uiso 0.268(10) 1 calc R . P A 1
O1' O 0.5293(2) 0.11579(18) 0.57420(7) 0.0687(5) Uani 1 1 d . . . . .
O2' O 0.3206(2) 0.20164(19) 0.54454(9) 0.0739(5) Uani 1 1 d . . . . .
O3' O 0.14318(16) 0.42474(15) 0.39147(10) 0.0654(4) Uani 1 1 d . . . . .
O4' O 0.07122(19) 0.81001(16) 0.36601(12) 0.0804(5) Uani 1 1 d . . . . .
O5' O 0.29746(16) 0.34175(15) 0.25562(8) 0.0624(4) Uani 1 1 d . . . . .
N1' N 0.62565(17) 0.10750(16) 0.38845(8) 0.0476(4) Uani 1 1 d . . . . .
N2' N 0.4366(2) 0.16023(17) 0.53064(9) 0.0552(5) Uani 1 1 d . . . . .
C1' C 0.5649(3) 0.1600(2) 0.20895(11) 0.0638(6) Uani 1 1 d . . . . .
H1' H 0.4772 0.2163 0.1944 0.077 Uiso 1 1 calc R . . . .
C2' C 0.6591(3) 0.1053(3) 0.16417(12) 0.0741(7) Uani 1 1 d . . . . .
H2' H 0.6336 0.1259 0.1195 0.089 Uiso 1 1 calc R . . . .
C3' C 0.7880(3) 0.0221(2) 0.18483(11) 0.0654(6) Uani 1 1 d . . . . .
H3' H 0.8494 -0.0127 0.1542 0.078 Uiso 1 1 calc R . . . .
C4' C 0.8280(2) -0.0107(2) 0.25111(12) 0.0597(5) Uani 1 1 d . . . . .
H4' H 0.9155 -0.0680 0.2654 0.072 Uiso 1 1 calc R . . . .
C5' C 0.7347(2) 0.0437(2) 0.29564(10) 0.0493(5) Uani 1 1 d . . . . .
C6' C 0.6039(2) 0.12935(19) 0.27531(9) 0.0468(4) Uani 1 1 d . . . . .
C7' C 0.7583(2) 0.0283(3) 0.36835(11) 0.0619(6) Uani 1 1 d . . . . .
H7'A H 0.7943 -0.0614 0.3885 0.074 Uiso 1 1 calc R . . . .
H7'B H 0.8176 0.0602 0.3794 0.074 Uiso 1 1 calc R . . . .
C8' C 0.5261(2) 0.18437(18) 0.33277(9) 0.0441(4) Uani 1 1 d . . . . .
H8' H 0.5051 0.2751 0.3295 0.053 Uiso 1 1 calc R . . . .
C9' C 0.4012(2) 0.17431(18) 0.34655(9) 0.0438(4) Uani 1 1 d . . . . .
H9' H 0.4218 0.0837 0.3497 0.053 Uiso 1 1 calc R . . . .
C10' C 0.3492(2) 0.22310(19) 0.41363(10) 0.0470(4) Uani 1 1 d . . . . .
H10' H 0.2872 0.1918 0.4280 0.056 Uiso 1 1 calc R . . . .
C11' C 0.4633(2) 0.16417(19) 0.46405(9) 0.0477(4) Uani 1 1 d . . . . .
C12' C 0.5916(2) 0.10537(19) 0.44906(9) 0.0479(5) Uani 1 1 d . . . . .
H12' H 0.6574 0.0622 0.4830 0.058 Uiso 1 1 calc R . . . .
C13' C 0.2773(2) 0.3681(2) 0.40593(10) 0.0486(4) Uani 1 1 d . . . . .
C14' C 0.3124(2) 0.4604(2) 0.40344(11) 0.0512(5) Uani 1 1 d . . . . .
H14' H 0.3974 0.4479 0.4106 0.061 Uiso 1 1 calc R . . . .
C15' C 0.1940(2) 0.5828(2) 0.38750(12) 0.0534(5) Uani 1 1 d . . . . .
C16' C 0.0949(2) 0.5555(2) 0.37998(15) 0.0665(6) Uani 1 1 d . . . . .
C17' C -0.0492(3) 0.6346(3) 0.3610(2) 0.1043(12) Uani 1 1 d . . . . .
H17D H -0.0760 0.5905 0.3340 0.156 Uiso 1 1 calc GR . . . .
H17E H -0.0671 0.7170 0.3371 0.156 Uiso 1 1 calc GR . . . .
H17F H -0.0972 0.6472 0.3998 0.156 Uiso 1 1 calc GR . . . .
C18' C 0.1784(2) 0.7144(2) 0.37727(13) 0.0623(6) Uani 1 1 d . . . . .
C19' C 0.3002(3) 0.7266(3) 0.3809(2) 0.1027(12) Uani 1 1 d . . . . .
H19D H 0.2773 0.8164 0.3730 0.154 Uiso 1 1 calc GR . . . .
H19E H 0.3572 0.6829 0.3484 0.154 Uiso 1 1 calc GR . . . .
H19F H 0.3448 0.6884 0.4238 0.154 Uiso 1 1 calc GR . . . .
C20' C 0.2916(2) 0.25592(19) 0.29266(9) 0.0465(4) Uani 1 1 d . . . . .
C21' C 0.1749(2) 0.2350(2) 0.28754(9) 0.0474(4) Uani 1 1 d . . . . .
C22' C 0.0592(2) 0.3369(2) 0.25562(11) 0.0574(5) Uani 1 1 d . . . . .
H22' H 0.0575 0.4141 0.2382 0.069 Uiso 1 1 calc R . . . .
C23' C -0.0525(3) 0.3247(3) 0.24962(13) 0.0678(6) Uani 1 1 d . . . . .
H23' H -0.1297 0.3937 0.2286 0.081 Uiso 1 1 calc R . . . .
C24' C -0.0499(3) 0.2094(3) 0.27500(14) 0.0715(7) Uani 1 1 d . . . . .
H24' H -0.1254 0.2010 0.2709 0.086 Uiso 1 1 calc R . . . .
C25' C 0.0635(3) 0.1079(3) 0.30612(13) 0.0687(7) Uani 1 1 d . . . . .
H25' H 0.0649 0.0305 0.3226 0.082 Uiso 1 1 calc R . . . .
C26' C 0.1765(3) 0.1198(2) 0.31323(11) 0.0588(5) Uani 1 1 d . . . . .
H26' H 0.2529 0.0510 0.3351 0.071 Uiso 1 1 calc R . . . .


_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 N2 1.245(2) . ?
O2 N2 1.237(3) . ?
O3 C13 1.381(2) . ?
O3 C16 1.368(3) . ?
O4 C18 1.206(3) . ?
O5 C20 1.209(2) . ?
N1 C7 1.464(3) . ?
N1 C8 1.478(2) . ?
N1 C12 1.322(3) . ?
N2 C11 1.405(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(4) . ?
C1 C6 1.384(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 C6 1.384(3) . ?
C5 C7 1.502(3) . ?
C6 C8 1.505(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C8 C9 1.538(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.567(3) . ?
C9 C20 1.526(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.501(3) . ?
C10 C13 1.502(3) . ?
C11 C12 1.362(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.329(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.447(3) . ?
C15 C16 1.361(3) . ?
C15 C18 1.468(3) . ?
C16 C17 1.499(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.506(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.379(13) . ?
C20 C21A 1.530(4) . ?
C21 C22 1.424(15) . ?
C21 C26 1.370(13) . ?
C21A C26A 1.3900 . ?
C21A C22A 1.3900 . ?
C26A H26A 0.9300 . ?
C26A C25A 1.3900 . ?
C25A H25A 0.9300 . ?
C25A C24A 1.3900 . ?
C24A H24A 0.9300 . ?
C24A C23A 1.3900 . ?
C23A H23A 0.9300 . ?
C23A C22A 1.3900 . ?
C22A H22A 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.399(17) . ?
C23 H23 0.9300 . ?
C23 C24 1.31(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.31(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.389(14) . ?
C26 H26 0.9300 . ?
O1' N2' 1.252(3) . ?
O2' N2' 1.237(3) . ?
O3' C13' 1.377(3) . ?
O3' C16' 1.365(3) . ?
O4' C18' 1.212(3) . ?
O5' C20' 1.217(2) . ?
N1' C7' 1.462(3) . ?
N1' C8' 1.482(2) . ?
N1' C12' 1.309(3) . ?
N2' C11' 1.406(3) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.395(4) . ?
C1' C6' 1.385(3) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.365(4) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.385(3) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.385(3) . ?
C5' C6' 1.386(3) . ?
C5' C7' 1.495(3) . ?
C6' C8' 1.513(3) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C8' H8' 0.9800 . ?
C8' C9' 1.526(3) . ?
C9' H9' 0.9800 . ?
C9' C10' 1.580(3) . ?
C9' C20' 1.524(3) . ?
C10' H10' 0.9800 . ?
C10' C11' 1.497(3) . ?
C10' C13' 1.501(3) . ?
C11' C12' 1.361(3) . ?
C12' H12' 0.9300 . ?
C13' C14' 1.335(3) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.441(3) . ?
C15' C16' 1.345(3) . ?
C15' C18' 1.474(3) . ?
C16' C17' 1.490(4) . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
C18' C19' 1.485(4) . ?
C19' H19D 0.9600 . ?
C19' H19E 0.9600 . ?
C19' H19F 0.9600 . ?
C20' C21' 1.490(3) . ?
C21' C22' 1.390(3) . ?
C21' C26' 1.391(3) . ?
C22' H22' 0.9300 . ?
C22' C23' 1.374(3) . ?
C23' H23' 0.9300 . ?
C23' C24' 1.385(4) . ?
C24' H24' 0.9300 . ?
C24' C25' 1.368(4) . ?
C25' H25' 0.9300 . ?
C25' C26' 1.389(4) . ?
C26' H26' 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O3 C13 107.37(17) . . ?
C7 N1 C8 113.72(16) . . ?
C12 N1 C7 124.37(17) . . ?
C12 N1 C8 120.74(16) . . ?
O1 N2 C11 119.78(19) . . ?
O2 N2 O1 121.71(19) . . ?
O2 N2 C11 118.51(19) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.7(2) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 C7 127.6(2) . . ?
C6 C5 C7 110.71(18) . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 C8 129.0(2) . . ?
C5 C6 C8 111.30(18) . . ?
N1 C7 C5 102.23(16) . . ?
N1 C7 H7A 111.3 . . ?
N1 C7 H7B 111.3 . . ?
C5 C7 H7A 111.3 . . ?
C5 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N1 C8 C6 101.49(15) . . ?
N1 C8 H8 109.9 . . ?
N1 C8 C9 107.58(15) . . ?
C6 C8 H8 109.9 . . ?
C6 C8 C9 117.68(16) . . ?
C9 C8 H8 109.9 . . ?
C8 C9 H9 108.2 . . ?
C8 C9 C10 109.88(15) . . ?
C10 C9 H9 108.2 . . ?
C20 C9 C8 111.24(15) . . ?
C20 C9 H9 108.2 . . ?
C20 C9 C10 111.03(15) . . ?
C9 C10 H10 107.8 . . ?
C11 C10 C9 107.94(15) . . ?
C11 C10 H10 107.8 . . ?
C11 C10 C13 111.30(17) . . ?
C13 C10 C9 113.98(16) . . ?
C13 C10 H10 107.8 . . ?
N2 C11 C10 118.41(17) . . ?
C12 C11 N2 118.48(18) . . ?
C12 C11 C10 122.88(18) . . ?
N1 C12 C11 122.65(18) . . ?
N1 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
O3 C13 C10 115.32(18) . . ?
C14 C13 O3 109.86(18) . . ?
C14 C13 C10 134.80(19) . . ?
C13 C14 H14 126.4 . . ?
C13 C14 C15 107.3(2) . . ?
C15 C14 H14 126.4 . . ?
C14 C15 C18 123.3(2) . . ?
C16 C15 C14 105.94(19) . . ?
C16 C15 C18 130.8(2) . . ?
O3 C16 C17 113.3(2) . . ?
C15 C16 O3 109.54(18) . . ?
C15 C16 C17 137.2(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 C15 119.9(2) . . ?
O4 C18 C19 120.3(3) . . ?
C15 C18 C19 119.7(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 C9 119.59(18) . . ?
O5 C20 C21 120.2(7) . . ?
O5 C20 C21A 121.3(3) . . ?
C9 C20 C21A 119.1(2) . . ?
C21 C20 C9 120.2(7) . . ?
C20 C21 C22 117.7(14) . . ?
C26 C21 C20 126.1(12) . . ?
C26 C21 C22 115.3(9) . . ?
C26A C21A C20 123.0(3) . . ?
C26A C21A C22A 120.0 . . ?
C22A C21A C20 116.9(3) . . ?
C21A C26A H26A 120.0 . . ?
C21A C26A C25A 120.0 . . ?
C25A C26A H26A 120.0 . . ?
C26A C25A H25A 120.0 . . ?
C26A C25A C24A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C25A C24A H24A 120.0 . . ?
C23A C24A C25A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C24A C23A H23A 120.0 . . ?
C24A C23A C22A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A C21A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.1(11) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.3(12) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(12) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 118.4 . . ?
C24 C25 C26 123.3(12) . . ?
C26 C25 H25 118.4 . . ?
C21 C26 C25 120.3(9) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C16' O3' C13' 107.76(17) . . ?
C7' N1' C8' 113.77(16) . . ?
C12' N1' C7' 124.85(17) . . ?
C12' N1' C8' 121.15(18) . . ?
O1' N2' C11' 120.0(2) . . ?
O2' N2' O1' 121.64(19) . . ?
O2' N2' C11' 118.4(2) . . ?
C2' C1' H1' 120.5 . . ?
C6' C1' H1' 120.5 . . ?
C6' C1' C2' 119.0(2) . . ?
C1' C2' H2' 119.5 . . ?
C3' C2' C1' 121.1(2) . . ?
C3' C2' H2' 119.5 . . ?
C2' C3' H3' 119.8 . . ?
C2' C3' C4' 120.5(2) . . ?
C4' C3' H3' 119.8 . . ?
C3' C4' H4' 120.7 . . ?
C5' C4' C3' 118.5(2) . . ?
C5' C4' H4' 120.7 . . ?
C4' C5' C6' 121.6(2) . . ?
C4' C5' C7' 127.1(2) . . ?
C6' C5' C7' 111.17(19) . . ?
C1' C6' C5' 119.3(2) . . ?
C1' C6' C8' 129.6(2) . . ?
C5' C6' C8' 110.90(17) . . ?
N1' C7' C5' 102.31(17) . . ?
N1' C7' H7'A 111.3 . . ?
N1' C7' H7'B 111.3 . . ?
C5' C7' H7'A 111.3 . . ?
C5' C7' H7'B 111.3 . . ?
H7'A C7' H7'B 109.2 . . ?
N1' C8' C6' 101.10(16) . . ?
N1' C8' H8' 108.8 . . ?
N1' C8' C9' 108.61(15) . . ?
C6' C8' H8' 108.8 . . ?
C6' C8' C9' 120.06(17) . . ?
C9' C8' H8' 108.8 . . ?
C8' C9' H9' 109.0 . . ?
C8' C9' C10' 109.86(16) . . ?
C10' C9' H9' 109.0 . . ?
C20' C9' C8' 111.77(15) . . ?
C20' C9' H9' 109.0 . . ?
C20' C9' C10' 108.03(16) . . ?
C9' C10' H10' 108.1 . . ?
C11' C10' C9' 108.64(17) . . ?
C11' C10' H10' 108.1 . . ?
C11' C10' C13' 112.23(17) . . ?
C13' C10' C9' 111.63(16) . . ?
C13' C10' H10' 108.1 . . ?
N2' C11' C10' 118.1(2) . . ?
C12' C11' N2' 118.18(19) . . ?
C12' C11' C10' 123.48(18) . . ?
N1' C12' C11' 122.30(18) . . ?
N1' C12' H12' 118.9 . . ?
C11' C12' H12' 118.9 . . ?
O3' C13' C10' 115.04(18) . . ?
C14' C13' O3' 109.13(18) . . ?
C14' C13' C10' 135.5(2) . . ?
C13' C14' H14' 126.4 . . ?
C13' C14' C15' 107.16(19) . . ?
C15' C14' H14' 126.4 . . ?
C14' C15' C18' 129.1(2) . . ?
C16' C15' C14' 106.4(2) . . ?
C16' C15' C18' 124.4(2) . . ?
O3' C16' C17' 116.0(2) . . ?
C15' C16' O3' 109.5(2) . . ?
C15' C16' C17' 134.5(2) . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
O4' C18' C15' 122.1(2) . . ?
O4' C18' C19' 120.5(2) . . ?
C15' C18' C19' 117.4(2) . . ?
C18' C19' H19D 109.5 . . ?
C18' C19' H19E 109.5 . . ?
C18' C19' H19F 109.5 . . ?
H19D C19' H19E 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
O5' C20' C9' 119.48(19) . . ?
O5' C20' C21' 120.28(18) . . ?
C21' C20' C9' 120.17(16) . . ?
C22' C21' C20' 117.55(18) . . ?
C22' C21' C26' 119.2(2) . . ?
C26' C21' C20' 123.3(2) . . ?
C21' C22' H22' 119.7 . . ?
C23' C22' C21' 120.7(2) . . ?
C23' C22' H22' 119.7 . . ?
C22' C23' H23' 120.1 . . ?
C22' C23' C24' 119.8(2) . . ?
C24' C23' H23' 120.1 . . ?
C23' C24' H24' 119.9 . . ?
C25' C24' C23' 120.2(2) . . ?
C25' C24' H24' 119.9 . . ?
C24' C25' H25' 119.8 . . ?
C24' C25' C26' 120.5(2) . . ?
C26' C25' H25' 119.8 . . ?
C21' C26' H26' 120.1 . . ?
C25' C26' C21' 119.7(2) . . ?
C25' C26' H26' 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C11 C10 178.13(17) . . . . ?
O1 N2 C11 C12 -7.1(3) . . . . ?
O2 N2 C11 C10 -2.7(3) . . . . ?
O2 N2 C11 C12 172.07(18) . . . . ?
O3 C13 C14 C15 0.9(2) . . . . ?
O5 C20 C21 C22 18(2) . . . . ?
O5 C20 C21 C26 -174.0(12) . . . . ?
O5 C20 C21A C26A 172.9(3) . . . . ?
O5 C20 C21A C22A -10.9(6) . . . . ?
N1 C8 C9 C10 -59.96(19) . . . . ?
N1 C8 C9 C20 176.68(15) . . . . ?
N2 C11 C12 N1 175.78(17) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C6 C8 N1 179.2(2) . . . . ?
C1 C6 C8 C9 -63.7(3) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C2 C1 C6 C8 -178.5(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C7 175.6(2) . . . . ?
C4 C5 C6 C1 1.8(3) . . . . ?
C4 C5 C6 C8 178.90(18) . . . . ?
C4 C5 C7 N1 177.7(2) . . . . ?
C5 C6 C8 N1 2.5(2) . . . . ?
C5 C6 C8 C9 119.54(18) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C6 C5 C7 N1 -5.8(2) . . . . ?
C6 C8 C9 C10 -173.67(15) . . . . ?
C6 C8 C9 C20 63.0(2) . . . . ?
C7 N1 C8 C6 -6.5(2) . . . . ?
C7 N1 C8 C9 -130.71(17) . . . . ?
C7 N1 C12 C11 164.30(19) . . . . ?
C7 C5 C6 C1 -174.92(19) . . . . ?
C7 C5 C6 C8 2.1(2) . . . . ?
C8 N1 C7 C5 7.7(2) . . . . ?
C8 N1 C12 C11 -2.5(3) . . . . ?
C8 C9 C10 C11 48.82(19) . . . . ?
C8 C9 C10 C13 -75.4(2) . . . . ?
C8 C9 C20 O5 38.1(3) . . . . ?
C8 C9 C20 C21 -140.1(10) . . . . ?
C8 C9 C20 C21A -141.1(3) . . . . ?
C9 C10 C11 N2 159.64(16) . . . . ?
C9 C10 C11 C12 -14.9(2) . . . . ?
C9 C10 C13 O3 -89.7(2) . . . . ?
C9 C10 C13 C14 88.8(3) . . . . ?
C9 C20 C21 C22 -164.1(11) . . . . ?
C9 C20 C21 C26 4.2(15) . . . . ?
C9 C20 C21A C26A -7.8(4) . . . . ?
C9 C20 C21A C22A 168.3(3) . . . . ?
C10 C9 C20 O5 -84.6(2) . . . . ?
C10 C9 C20 C21 97.2(10) . . . . ?
C10 C9 C20 C21A 96.2(3) . . . . ?
C10 C11 C12 N1 -9.7(3) . . . . ?
C10 C13 C14 C15 -177.7(2) . . . . ?
C11 C10 C13 O3 147.91(17) . . . . ?
C11 C10 C13 C14 -33.6(3) . . . . ?
C12 N1 C7 C5 -159.94(18) . . . . ?
C12 N1 C8 C6 161.62(16) . . . . ?
C12 N1 C8 C9 37.5(2) . . . . ?
C13 O3 C16 C15 0.1(2) . . . . ?
C13 O3 C16 C17 -178.7(2) . . . . ?
C13 C10 C11 N2 -74.6(2) . . . . ?
C13 C10 C11 C12 110.9(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C13 C14 C15 C18 177.1(2) . . . . ?
C14 C15 C16 O3 0.4(3) . . . . ?
C14 C15 C16 C17 178.8(3) . . . . ?
C14 C15 C18 O4 -0.8(4) . . . . ?
C14 C15 C18 C19 -178.6(3) . . . . ?
C16 O3 C13 C10 178.25(17) . . . . ?
C16 O3 C13 C14 -0.6(2) . . . . ?
C16 C15 C18 O4 176.6(3) . . . . ?
C16 C15 C18 C19 -1.2(4) . . . . ?
C18 C15 C16 O3 -177.3(2) . . . . ?
C18 C15 C16 C17 1.1(5) . . . . ?
C20 C9 C10 C11 172.30(15) . . . . ?
C20 C9 C10 C13 48.1(2) . . . . ?
C20 C21 C22 C23 174.6(13) . . . . ?
C20 C21 C26 C25 -168.7(19) . . . . ?
C20 C21A C26A C25A 176.0(5) . . . . ?
C20 C21A C22A C23A -176.3(5) . . . . ?
C21 C22 C23 C24 -7(2) . . . . ?
C21A C26A C25A C24A 0.0 . . . . ?
C26A C21A C22A C23A 0.0 . . . . ?
C26A C25A C24A C23A 0.0 . . . . ?
C25A C24A C23A C22A 0.0 . . . . ?
C24A C23A C22A C21A 0.0 . . . . ?
C22A C21A C26A C25A 0.0 . . . . ?
C22 C21 C26 C25 -0.2(18) . . . . ?
C22 C23 C24 C25 4(3) . . . . ?
C23 C24 C25 C26 1(3) . . . . ?
C24 C25 C26 C21 -3(2) . . . . ?
C26 C21 C22 C23 5.0(19) . . . . ?
O1' N2' C11' C10' -177.51(18) . . . . ?
O1' N2' C11' C12' 7.5(3) . . . . ?
O2' N2' C11' C10' 2.3(3) . . . . ?
O2' N2' C11' C12' -172.66(19) . . . . ?
O3' C13' C14' C15' 0.9(3) . . . . ?
O5' C20' C21' C22' -20.0(3) . . . . ?
O5' C20' C21' C26' 160.3(2) . . . . ?
N1' C8' C9' C10' 57.6(2) . . . . ?
N1' C8' C9' C20' 177.51(15) . . . . ?
N2' C11' C12' N1' -177.97(18) . . . . ?
C1' C2' C3' C4' 0.5(5) . . . . ?
C1' C6' C8' N1' 179.0(2) . . . . ?
C1' C6' C8' C9' 59.7(3) . . . . ?
C2' C1' C6' C5' -1.0(4) . . . . ?
C2' C1' C6' C8' 173.3(2) . . . . ?
C2' C3' C4' C5' -0.6(4) . . . . ?
C3' C4' C5' C6' -0.1(4) . . . . ?
C3' C4' C5' C7' -175.7(2) . . . . ?
C4' C5' C6' C1' 1.0(3) . . . . ?
C4' C5' C6' C8' -174.3(2) . . . . ?
C4' C5' C7' N1' 179.5(2) . . . . ?
C5' C6' C8' N1' -6.3(2) . . . . ?
C5' C6' C8' C9' -125.61(19) . . . . ?
C6' C1' C2' C3' 0.3(5) . . . . ?
C6' C5' C7' N1' 3.6(3) . . . . ?
C6' C8' C9' C10' 173.04(16) . . . . ?
C6' C8' C9' C20' -67.0(2) . . . . ?
C7' N1' C8' C6' 8.9(2) . . . . ?
C7' N1' C8' C9' 136.13(19) . . . . ?
C7' N1' C12' C11' -168.7(2) . . . . ?
C7' C5' C6' C1' 177.2(2) . . . . ?
C7' C5' C6' C8' 1.9(3) . . . . ?
C8' N1' C7' C5' -8.0(2) . . . . ?
C8' N1' C12' C11' 5.5(3) . . . . ?
C8' C9' C10' C11' -46.0(2) . . . . ?
C8' C9' C10' C13' 78.3(2) . . . . ?
C8' C9' C20' O5' -18.4(3) . . . . ?
C8' C9' C20' C21' 164.68(17) . . . . ?
C9' C10' C11' N2' -160.39(16) . . . . ?
C9' C10' C11' C12' 14.3(3) . . . . ?
C9' C10' C13' O3' 91.5(2) . . . . ?
C9' C10' C13' C14' -80.6(3) . . . . ?
C9' C20' C21' C22' 156.90(19) . . . . ?
C9' C20' C21' C26' -22.8(3) . . . . ?
C10' C9' C20' O5' 102.6(2) . . . . ?
C10' C9' C20' C21' -74.3(2) . . . . ?
C10' C11' C12' N1' 7.3(3) . . . . ?
C10' C13' C14' C15' 173.4(2) . . . . ?
C11' C10' C13' O3' -146.21(19) . . . . ?
C11' C10' C13' C14' 41.6(3) . . . . ?
C12' N1' C7' C5' 166.49(19) . . . . ?
C12' N1' C8' C6' -165.80(18) . . . . ?
C12' N1' C8' C9' -38.6(2) . . . . ?
C13' O3' C16' C15' -0.7(3) . . . . ?
C13' O3' C16' C17' 177.9(3) . . . . ?
C13' C10' C11' N2' 75.7(2) . . . . ?
C13' C10' C11' C12' -109.6(2) . . . . ?
C13' C14' C15' C16' -1.3(3) . . . . ?
C13' C14' C15' C18' -178.3(2) . . . . ?
C14' C15' C16' O3' 1.2(3) . . . . ?
C14' C15' C16' C17' -177.0(4) . . . . ?
C14' C15' C18' O4' -177.6(3) . . . . ?
C14' C15' C18' C19' 2.7(4) . . . . ?
C16' O3' C13' C10' -174.3(2) . . . . ?
C16' O3' C13' C14' -0.2(3) . . . . ?
C16' C15' C18' O4' 5.9(4) . . . . ?
C16' C15' C18' C19' -173.8(3) . . . . ?
C18' C15' C16' O3' 178.4(2) . . . . ?
C18' C15' C16' C17' 0.1(6) . . . . ?
C20' C9' C10' C11' -168.15(16) . . . . ?
C20' C9' C10' C13' -43.9(2) . . . . ?
C20' C21' C22' C23' -179.4(2) . . . . ?
C20' C21' C26' C25' -179.7(2) . . . . ?
C21' C22' C23' C24' -0.7(4) . . . . ?
C22' C21' C26' C25' 0.6(3) . . . . ?
C22' C23' C24' C25' 0.2(4) . . . . ?
C23' C24' C25' C26' 0.7(4) . . . . ?
C24' C25' C26' C21' -1.1(4) . . . . ?
C26' C21' C22' C23' 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.086
_oxdiff_exptl_absorpt_empirical_full_min 0.766
####################################################################### 
# 
# 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_hd_wql34
_database_code_depnum_ccdc_archive 'CCDC 2086415'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C26 H24 N2 O3'
_chemical_formula_sum            'C26 H24 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         412.47

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.8952(8)
_cell_length_b                   8.6715(6)
_cell_length_c                   21.1913(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.064(2)
_cell_angle_gamma                90
_cell_volume                     2180.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      4.1415
_cell_measurement_theta_max      72.4441
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872

_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            21965
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         72.52
_diffrn_reflns_theta_full        72.52
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             4310
_reflns_number_gt                3685
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_gt          0.2043
_refine_ls_wR_factor_ref         0.2161
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_number_reflns         4310
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1537P)²+0.3407P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.384
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.67648(14) 0.62278(19) 0.76482(7) 0.0458(4) Uani d . . . 1 . .
O O2 0.07823(13) 0.82441(16) 0.61041(6) 0.0375(4) Uani d . . . 1 . .
O O3 0.66820(17) 0.5182(2) 0.66841(8) 0.0608(5) Uani d . . . 1 . .
N N1 0.22901(15) 0.49422(19) 0.49927(7) 0.0353(4) Uani d . . . 1 . .
N N2 0.54035(17) 0.8208(2) 0.46963(8) 0.0446(4) Uani d . . . 1 . .
C C1 0.17792(19) 0.7217(2) 0.83879(8) 0.0394(5) Uani d . . . 1 . .
H H1 0.183817 0.719476 0.88372 0.047 Uiso calc U . R 1 . .
C C2 0.26058(19) 0.6535(2) 0.80550(8) 0.0387(5) Uani d . . . 1 . .
H H18 0.323487 0.605537 0.827611 0.046 Uiso calc U . R 1 . .
C C3 0.25174(17) 0.6549(2) 0.73963(8) 0.0353(4) Uani d . . . 1 . .
H H15 0.307497 0.605325 0.716881 0.042 Uiso calc U . R 1 . .
C C4 0.16125(16) 0.7290(2) 0.70696(8) 0.0318(4) Uani d . . . 1 . .
C C5 0.15078(16) 0.7420(2) 0.63651(8) 0.0306(4) Uani d . . . 1 . .
C C6 0.22942(16) 0.6559(2) 0.59513(8) 0.0301(4) Uani d . . . 1 . .
H H6 0.276059 0.580154 0.621151 0.036 Uiso calc U . R 1 . .
C C7 0.30684(16) 0.7741(2) 0.56416(8) 0.0319(4) Uani d . . . 1 . .
H H19 0.258963 0.861792 0.547386 0.038 Uiso calc U . R 1 . .
C C8 0.39744(17) 0.8394(2) 0.61319(8) 0.0334(4) Uani d . . . 1 . .
H H5 0.433215 0.930117 0.594513 0.04 Uiso calc U . R 1 . .
H H20 0.359757 0.875399 0.650688 0.04 Uiso calc U . R 1 . .
C C9 0.48737(17) 0.7269(2) 0.63436(8) 0.0353(4) Uani d . . . 1 . .
H H21 0.513121 0.659726 0.603023 0.042 Uiso calc U . R 1 . .
C C10 0.53494(17) 0.7112(2) 0.69262(9) 0.0355(4) Uani d . . . 1 . .
H H22 0.506551 0.768102 0.726356 0.043 Uiso calc U . R 1 . .
C C11 0.63175(18) 0.6060(2) 0.70544(9) 0.0386(5) Uani d . . . 1 . .
C C12 0.7782(2) 0.5359(3) 0.78181(12) 0.0579(7) Uani d . . . 1 . .
H H23 0.836997 0.560916 0.752592 0.069 Uiso calc U . R 1 . .
H H24 0.762575 0.423905 0.779109 0.069 Uiso calc U . R 1 . .
C C13 0.8176(3) 0.5792(4) 0.84815(12) 0.0626(7) Uani d . . . 1 . .
H H3 0.823415 0.691644 0.851516 0.094 Uiso calc U . R 1 . .
H H4 0.891536 0.532794 0.859023 0.094 Uiso calc U . R 1 . .
H H2 0.763458 0.541387 0.877336 0.094 Uiso calc U . R 1 . .
C C14 0.15656(16) 0.5711(2) 0.54283(8) 0.0317(4) Uani d . . . 1 . .
H H14 0.106737 0.646999 0.518871 0.038 Uiso calc U . R 1 . .
C C15 0.08668(16) 0.4392(2) 0.56413(8) 0.0333(4) Uani d . . . 1 . .
C C16 0.00400(17) 0.4392(2) 0.60746(8) 0.0354(4) Uani d . . . 1 . .
H H13 -0.014395 0.531501 0.628546 0.042 Uiso calc U . R 1 . .
C C17 -0.05121(19) 0.3023(2) 0.61942(9) 0.0406(5) Uani d . . . 1 . .
H H12 -0.10857 0.301241 0.648416 0.049 Uiso calc U . R 1 . .
C C18 -0.0230(2) 0.1661(2) 0.58913(10) 0.0435(5) Uani d . . . 1 . .
H H7 -0.060037 0.072651 0.598431 0.052 Uiso calc U . R 1 . .
C C19 0.05882(19) 0.1662(2) 0.54553(10) 0.0412(5) Uani d . . . 1 . .
H H8 0.077937 0.073683 0.524791 0.049 Uiso calc U . R 1 . .
C C20 0.11212(17) 0.3040(2) 0.53281(8) 0.0360(4) Uani d . . . 1 . .
C C21 0.19860(18) 0.3329(2) 0.48585(9) 0.0377(5) Uani d . . . 1 . .
H H10 0.26444 0.263688 0.493221 0.045 Uiso calc U . R 1 . .
H H9 0.166187 0.319805 0.441844 0.045 Uiso calc U . R 1 . .
C C22 0.32271(17) 0.5636(2) 0.48259(8) 0.0358(4) Uani d . . . 1 . .
H H11 0.364484 0.516714 0.451168 0.043 Uiso calc U . R 1 . .
C C23 0.36074(17) 0.6991(2) 0.50887(8) 0.0342(4) Uani d . . . 1 . .
C C24 0.45949(18) 0.7661(2) 0.48632(8) 0.0374(5) Uani d . . . 1 . .
C C25 0.08647(19) 0.7933(2) 0.80685(9) 0.0411(5) Uani d . . . 1 . .
H H16 0.02948 0.839232 0.829858 0.049 Uiso calc U . R 1 . .
C C26 0.07832(18) 0.7979(2) 0.74103(9) 0.0373(4) Uani d . . . 1 . .
H H17 0.016109 0.848046 0.719183 0.045 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . 1.339(2) ?
O1 C12 . 1.449(3) ?
O2 C5 . 1.222(2) ?
O3 C11 . 1.196(3) ?
N1 C22 . 1.336(3) ?
N1 C14 . 1.467(2) ?
N1 C21 . 1.468(3) ?
N2 C24 . 1.150(3) ?
C1 C2 . 1.383(3) ?
C1 C25 . 1.387(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.392(2) ?
C2 H18 . 0.95 ?
C3 C4 . 1.395(3) ?
C3 H15 . 0.95 ?
C4 C26 . 1.397(3) ?
C4 C5 . 1.494(2) ?
C5 C6 . 1.522(2) ?
C6 C14 . 1.544(2) ?
C6 C7 . 1.554(2) ?
C6 H6 . 1.0 ?
C7 C23 . 1.521(2) ?
C7 C8 . 1.550(3) ?
C7 H19 . 1.0 ?
C8 C9 . 1.493(3) ?
C8 H5 . 0.99 ?
C8 H20 . 0.99 ?
C9 C10 . 1.328(3) ?
C9 H21 . 0.95 ?
C10 C11 . 1.479(3) ?
C10 H22 . 0.95 ?
C12 C13 . 1.498(3) ?
C12 H23 . 0.99 ?
C12 H24 . 0.99 ?
C13 H3 . 0.98 ?
C13 H4 . 0.98 ?
C13 H2 . 0.98 ?
C14 C15 . 1.502(3) ?
C14 H14 . 1.0 ?
C15 C20 . 1.392(3) ?
C15 C16 . 1.392(3) ?
C16 C17 . 1.389(3) ?
C16 H13 . 0.95 ?
C17 C18 . 1.396(3) ?
C17 H12 . 0.95 ?
C18 C19 . 1.389(3) ?
C18 H7 . 0.95 ?
C19 C20 . 1.388(3) ?
C19 H8 . 0.95 ?
C20 C21 . 1.502(3) ?
C21 H10 . 0.99 ?
C21 H9 . 0.99 ?
C22 C23 . 1.364(3) ?
C22 H11 . 0.95 ?
C23 C24 . 1.423(3) ?
C25 C26 . 1.392(3) ?
C25 H16 . 0.95 ?
C26 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 C12 . . 116.51(16) ?
C22 N1 C14 . . 120.02(16) ?
C22 N1 C21 . . 125.22(16) ?
C14 N1 C21 . . 114.04(16) ?
C2 C1 C25 . . 120.28(17) ?
C2 C1 H1 . . 119.9 ?
C25 C1 H1 . . 119.9 ?
C1 C2 C3 . . 120.10(19) ?
C1 C2 H18 . . 120.0 ?
C3 C2 H18 . . 120.0 ?
C2 C3 C4 . . 120.17(18) ?
C2 C3 H15 . . 119.9 ?
C4 C3 H15 . . 119.9 ?
C3 C4 C26 . . 119.26(16) ?
C3 C4 C5 . . 122.52(17) ?
C26 C4 C5 . . 118.19(17) ?
O2 C5 C4 . . 120.17(16) ?
O2 C5 C6 . . 117.97(15) ?
C4 C5 C6 . . 121.86(16) ?
C5 C6 C14 . . 108.08(15) ?
C5 C6 C7 . . 109.07(14) ?
C14 C6 C7 . . 109.29(13) ?
C5 C6 H6 . . 110.1 ?
C14 C6 H6 . . 110.1 ?
C7 C6 H6 . . 110.1 ?
C23 C7 C8 . . 111.20(16) ?
C23 C7 C6 . . 109.75(15) ?
C8 C7 C6 . . 111.25(14) ?
C23 C7 H19 . . 108.2 ?
C8 C7 H19 . . 108.2 ?
C6 C7 H19 . . 108.2 ?
C9 C8 C7 . . 114.31(15) ?
C9 C8 H5 . . 108.7 ?
C7 C8 H5 . . 108.7 ?
C9 C8 H20 . . 108.7 ?
C7 C8 H20 . . 108.7 ?
H5 C8 H20 . . 107.6 ?
C10 C9 C8 . . 126.50(17) ?
C10 C9 H21 . . 116.7 ?
C8 C9 H21 . . 116.7 ?
C9 C10 C11 . . 120.56(17) ?
C9 C10 H22 . . 119.7 ?
C11 C10 H22 . . 119.7 ?
O3 C11 O1 . . 123.17(19) ?
O3 C11 C10 . . 125.85(18) ?
O1 C11 C10 . . 110.97(16) ?
O1 C12 C13 . . 107.63(18) ?
O1 C12 H23 . . 110.2 ?
C13 C12 H23 . . 110.2 ?
O1 C12 H24 . . 110.2 ?
C13 C12 H24 . . 110.2 ?
H23 C12 H24 . . 108.5 ?
C12 C13 H3 . . 109.5 ?
C12 C13 H4 . . 109.5 ?
H3 C13 H4 . . 109.5 ?
C12 C13 H2 . . 109.5 ?
H3 C13 H2 . . 109.5 ?
H4 C13 H2 . . 109.5 ?
N1 C14 C15 . . 101.87(15) ?
N1 C14 C6 . . 110.08(15) ?
C15 C14 C6 . . 116.20(14) ?
N1 C14 H14 . . 109.5 ?
C15 C14 H14 . . 109.5 ?
C6 C14 H14 . . 109.5 ?
C20 C15 C16 . . 120.13(18) ?
C20 C15 C14 . . 110.77(17) ?
C16 C15 C14 . . 129.09(17) ?
C17 C16 C15 . . 119.08(19) ?
C17 C16 H13 . . 120.5 ?
C15 C16 H13 . . 120.5 ?
C16 C17 C18 . . 120.4(2) ?
C16 C17 H12 . . 119.8 ?
C18 C17 H12 . . 119.8 ?
C19 C18 C17 . . 120.56(19) ?
C19 C18 H7 . . 119.7 ?
C17 C18 H7 . . 119.7 ?
C20 C19 C18 . . 118.74(19) ?
C20 C19 H8 . . 120.6 ?
C18 C19 H8 . . 120.6 ?
C19 C20 C15 . . 121.0(2) ?
C19 C20 C21 . . 128.02(19) ?
C15 C20 C21 . . 110.96(17) ?
N1 C21 C20 . . 101.62(15) ?
N1 C21 H10 . . 111.4 ?
C20 C21 H10 . . 111.4 ?
N1 C21 H9 . . 111.4 ?
C20 C21 H9 . . 111.4 ?
H10 C21 H9 . . 109.3 ?
N1 C22 C23 . . 122.60(17) ?
N1 C22 H11 . . 118.7 ?
C23 C22 H11 . . 118.7 ?
C22 C23 C24 . . 118.20(17) ?
C22 C23 C7 . . 122.51(18) ?
C24 C23 C7 . . 119.14(17) ?
N2 C24 C23 . . 178.3(2) ?
C1 C25 C26 . . 119.89(19) ?
C1 C25 H16 . . 120.1 ?
C26 C25 H16 . . 120.1 ?
C25 C26 C4 . . 120.3(2) ?
C25 C26 H17 . . 119.9 ?
C4 C26 H17 . . 119.9 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C25 C1 C2 C3 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 1.9(3) ?
C2 C3 C4 C26 . . . . -1.7(3) ?
C2 C3 C4 C5 . . . . 176.48(18) ?
C3 C4 C5 O2 . . . . -170.60(18) ?
C26 C4 C5 O2 . . . . 7.6(3) ?
C3 C4 C5 C6 . . . . 8.7(3) ?
C26 C4 C5 C6 . . . . -173.06(17) ?
O2 C5 C6 C14 . . . . -50.5(2) ?
C4 C5 C6 C14 . . . . 130.15(17) ?
O2 C5 C6 C7 . . . . 68.2(2) ?
C4 C5 C6 C7 . . . . -111.12(18) ?
C5 C6 C7 C23 . . . . -163.48(14) ?
C14 C6 C7 C23 . . . . -45.51(19) ?
C5 C6 C7 C8 . . . . 73.02(18) ?
C14 C6 C7 C8 . . . . -169.01(15) ?
C23 C7 C8 C9 . . . . -51.5(2) ?
C6 C7 C8 C9 . . . . 71.2(2) ?
C7 C8 C9 C10 . . . . -141.2(2) ?
C8 C9 C10 C11 . . . . -173.40(19) ?
C12 O1 C11 O3 . . . . 4.2(4) ?
C12 O1 C11 C10 . . . . -174.8(2) ?
C9 C10 C11 O3 . . . . -7.3(4) ?
C9 C10 C11 O1 . . . . 171.57(19) ?
C11 O1 C12 C13 . . . . 176.4(2) ?
C22 N1 C14 C15 . . . . -162.80(16) ?
C21 N1 C14 C15 . . . . 7.91(19) ?
C22 N1 C14 C6 . . . . -38.9(2) ?
C21 N1 C14 C6 . . . . 131.77(16) ?
C5 C6 C14 N1 . . . . 176.44(14) ?
C7 C6 C14 N1 . . . . 57.85(19) ?
C5 C6 C14 C15 . . . . -68.48(19) ?
C7 C6 C14 C15 . . . . 172.94(15) ?
N1 C14 C15 C20 . . . . -3.41(19) ?
C6 C14 C15 C20 . . . . -123.04(17) ?
N1 C14 C15 C16 . . . . 178.04(18) ?
C6 C14 C15 C16 . . . . 58.4(3) ?
C20 C15 C16 C17 . . . . 0.8(3) ?
C14 C15 C16 C17 . . . . 179.28(18) ?
C15 C16 C17 C18 . . . . 1.0(3) ?
C16 C17 C18 C19 . . . . -1.5(3) ?
C17 C18 C19 C20 . . . . 0.2(3) ?
C18 C19 C20 C15 . . . . 1.6(3) ?
C18 C19 C20 C21 . . . . -177.08(18) ?
C16 C15 C20 C19 . . . . -2.2(3) ?
C14 C15 C20 C19 . . . . 179.13(17) ?
C16 C15 C20 C21 . . . . 176.75(16) ?
C14 C15 C20 C21 . . . . -2.0(2) ?
C22 N1 C21 C20 . . . . 161.20(17) ?
C14 N1 C21 C20 . . . . -8.9(2) ?
C19 C20 C21 N1 . . . . -174.79(19) ?
C15 C20 C21 N1 . . . . 6.4(2) ?
C14 N1 C22 C23 . . . . 6.2(3) ?
C21 N1 C22 C23 . . . . -163.44(18) ?
N1 C22 C23 C24 . . . . -177.98(17) ?
N1 C22 C23 C7 . . . . 6.6(3) ?
C8 C7 C23 C22 . . . . 138.51(18) ?
C6 C7 C23 C22 . . . . 15.0(2) ?
C8 C7 C23 C24 . . . . -36.9(2) ?
C6 C7 C23 C24 . . . . -160.42(16) ?
C2 C1 C25 C26 . . . . -0.6(3) ?
C1 C25 C26 C4 . . . . 0.7(3) ?
C3 C4 C26 C25 . . . . 0.4(3) ?
C5 C4 C26 C25 . . . . -177.85(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C21 H10 N2 3_666 0.99 2.51 3.449(3) 158.6 ?
C22 H11 O3 3_666 0.95 2.55 3.287(2) 134.1 ?



####################################################################### 
# 
# 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_zzy119
_database_code_depnum_ccdc_archive 'CCDC 2086418'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2020-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 N4 O3'
_chemical_formula_sum            'C26 H26 N4 O3'
_chemical_formula_weight         442.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4
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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5216(3)
_cell_length_b                   10.7823(4)
_cell_length_c                   12.6332(5)
_cell_angle_alpha                106.178(4)
_cell_angle_beta                 93.800(3)
_cell_angle_gamma                114.614(3)
_cell_volume                     1107.47(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7780
_cell_measurement_theta_min      4.7750
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         3.725
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  35.00   0.50    1.50    --  -33.50  57.00 -60.00  174
  2  ω   -108.00 -32.00   0.50    1.50    --  -33.50 178.00 120.00  152
  3  ω   -102.00 -15.00   0.50    1.50    --  -33.50 -57.00 150.00  174
  4  ω    -34.00  59.00   0.50    1.50    --   36.47 -37.00-120.00  186
  5  ω     57.00 110.00   0.50    1.50    --   36.47 178.00-180.00  106
  6  ω     57.00 110.00   0.50    1.50    --   36.47 178.00 150.00  106
  7  ω     14.00 107.00   0.50    1.50    --   36.47  37.00  60.00  186
  8  ω     -4.00  53.00   0.50    1.50    --   36.47 -99.00  30.00  114
  9  ω     11.00  40.00   0.50    1.50    --   36.47  77.00  60.00   58
 10  ω    -32.00  19.00   0.50    1.50    --   36.47 -77.00 120.00  102
 11  ω     40.00  65.00   0.50    1.50    --   36.47 -77.00 120.00   50
 12  ω     31.00 105.00   0.50    1.50    --   36.47  57.00 -30.00  148
 13  ω     19.00  72.00   0.50    1.50    --   36.47 -99.00 120.00  106
 14  ω      5.00  75.00   0.50    1.50    --   36.47 -99.00 -90.00  140
 15  ω     61.00 105.00   0.50    1.50    --   36.47  77.00  60.00   88
 16  ω    152.00 178.00   0.50    6.50    --  108.00 111.00 150.00   52
 17  ω     44.00  99.00   0.50    6.50    --  108.00-111.00 150.00  110
 18  ω     38.00 127.00   0.50    6.50    --  108.00 -45.00   0.00  178
 19  ω     80.00 132.00   0.50    6.50    --  108.00 -77.00  90.00  104
 20  ω     76.00 108.00   0.50    6.50    --  108.00 -94.00 -60.00   64
 21  ω     45.00 123.00   0.50    6.50    --  108.00 -45.00-180.00  156
 22  ω     97.00 149.00   0.50    6.50    --  108.00  30.00  30.00  104
 23  ω     37.00 122.00   0.50    6.50    --  108.00 -30.00  90.00  170
 24  ω     76.00 109.00   0.50    6.50    --  108.00 -94.00-180.00   66
 25  ω     68.00 109.00   0.50    6.50    --  108.00-111.00  90.00   82
 26  ω     40.00 127.00   0.50    6.50    --  108.00 -45.00 -90.00  174
 27  ω     60.00 101.00   0.50    6.50    --  108.00 -94.00 -90.00   82
 28  ω     38.00 178.00   0.50    6.50    --  108.00   0.00 150.00  280
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0063998000
_diffrn_orient_matrix_UB_12      0.0251273000
_diffrn_orient_matrix_UB_13      0.1253772000
_diffrn_orient_matrix_UB_21      -0.1810276000
_diffrn_orient_matrix_UB_22      -0.0903974000
_diffrn_orient_matrix_UB_23      -0.0325428000
_diffrn_orient_matrix_UB_31      0.0174674000
_diffrn_orient_matrix_UB_32      -0.1381035000
_diffrn_orient_matrix_UB_33      -0.0088731000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2883
_reflns_number_total             3949
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3949
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.063
_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)+(0.1040P)²+0.0918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C21A-N4
 1.45 with sigma of 0.02
 C25A-C24A
 1.52 with sigma of 0.02
 C24A-C23A
 1.52 with sigma of 0.02
 C26A-C25A
 1.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N4) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(N4) = Uanis(N4A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
Uanis(C26) = Uanis(C26A)
4. Others
 Sof(N4A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22C)=
 Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24C)=Sof(H24D)=
 Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=1-FVAR(1)
 Sof(N4)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=
 Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C22(H22A,H22B), C22A(H22C,H22D), C23(H23A,H23B), C23A(H23C,
 H23D), C24(H24A,H24B), C24A(H24C,H24D), C25(H25A,H25B), C25A(H25C,H25D),
 C26(H26A,H26B), C26A(H26C,H26D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C20A(H20A), C21(H21), C21A(H21A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.89738(19) 0.31207(18) 0.50692(17) 0.0676(5) Uani 1 1 d . . . . .
O2 O 0.5901(4) -0.3333(3) 0.1411(2) 0.1162(10) Uani 1 1 d . . . . .
O3 O 0.8335(4) -0.1799(3) 0.2243(2) 0.1010(9) Uani 1 1 d . . . . .
N1 N 0.8373(2) 0.4069(2) 0.37849(19) 0.0578(5) Uani 1 1 d . . . . .
H1 H 0.9039 0.4964 0.4120 0.069 Uiso 1 1 calc R . . . .
N2 N 0.4428(2) -0.05588(19) 0.31626(17) 0.0556(5) Uani 1 1 d . . . . .
N3 N 0.6913(4) -0.2119(3) 0.2005(2) 0.0836(8) Uani 1 1 d . . . . .
N4 N 1.1080(7) 0.2046(7) 0.1508(5) 0.0908(17) Uani 0.763(5) 1 d D U P A 1
N4A N 1.057(3) 0.169(3) 0.108(2) 0.0908(17) Uani 0.237(5) 1 d . . P A 2
C1 C 0.8214(2) 0.2996(2) 0.4190(2) 0.0521(5) Uani 1 1 d . . . . .
C2 C 0.6917(3) 0.1563(2) 0.33495(19) 0.0478(5) Uani 1 1 d . . . . .
C3 C 0.6406(3) 0.2055(2) 0.24592(19) 0.0511(5) Uani 1 1 d . . . . .
C4 C 0.7327(3) 0.3553(2) 0.2755(2) 0.0516(5) Uani 1 1 d . . . . .
C5 C 0.7174(3) 0.4325(3) 0.2093(2) 0.0612(6) Uani 1 1 d . . . . .
H5 H 0.7798 0.5322 0.2310 0.073 Uiso 1 1 calc R . . . .
C6 C 0.6066(4) 0.3574(3) 0.1098(2) 0.0733(8) Uani 1 1 d . . . . .
H6 H 0.5936 0.4068 0.0633 0.088 Uiso 1 1 calc R . . . .
C7 C 0.5146(4) 0.2093(3) 0.0782(2) 0.0796(9) Uani 1 1 d . . . . .
H7 H 0.4410 0.1605 0.0103 0.096 Uiso 1 1 calc R . . . .
C8 C 0.5299(4) 0.1315(3) 0.1462(2) 0.0686(7) Uani 1 1 d . . . . .
H8 H 0.4668 0.0320 0.1246 0.082 Uiso 1 1 calc R . . . .
C9 C 0.5605(2) 0.0844(2) 0.39509(18) 0.0448(5) Uani 1 1 d . . . . .
H9 H 0.6084 0.0673 0.4572 0.054 Uiso 1 1 calc R . . . .
C10 C 0.2793(3) -0.0823(3) 0.3183(3) 0.0709(7) Uani 1 1 d . . . . .
H10A H 0.2240 -0.1626 0.3446 0.085 Uiso 1 1 calc R . . . .
H10B H 0.2219 -0.1017 0.2444 0.085 Uiso 1 1 calc R . . . .
C11 C 0.3015(3) 0.0579(3) 0.4000(2) 0.0597(6) Uani 1 1 d . . . . .
C12 C 0.4598(3) 0.1551(2) 0.43977(18) 0.0486(5) Uani 1 1 d . . . . .
C13 C 0.5047(3) 0.2914(3) 0.5165(2) 0.0631(6) Uani 1 1 d . . . . .
H13 H 0.6111 0.3575 0.5423 0.076 Uiso 1 1 calc R . . . .
C14 C 0.3899(4) 0.3285(4) 0.5544(3) 0.0821(9) Uani 1 1 d . . . . .
H14 H 0.4191 0.4203 0.6055 0.099 Uiso 1 1 calc R . . . .
C15 C 0.2325(4) 0.2302(4) 0.5169(3) 0.0896(10) Uani 1 1 d . . . . .
H15 H 0.1564 0.2556 0.5442 0.108 Uiso 1 1 calc R . . . .
C16 C 0.1864(3) 0.0947(4) 0.4394(3) 0.0819(9) Uani 1 1 d . . . . .
H16 H 0.0800 0.0290 0.4139 0.098 Uiso 1 1 calc R . . . .
C17 C 0.4915(3) -0.1446(2) 0.2528(2) 0.0622(7) Uani 1 1 d . . . . .
H17 H 0.4181 -0.2389 0.2102 0.075 Uiso 1 1 calc R . . . .
C18 C 0.6453(4) -0.1006(3) 0.2489(2) 0.0630(7) Uani 1 1 d . . . . .
C19 C 0.7694(3) 0.0521(3) 0.2952(3) 0.0633(7) Uani 1 1 d . . . . .
H19 H 0.834(4) 0.069(3) 0.363(3) 0.076 Uiso 1 1 d R . . . .
C20 C 0.8552(4) 0.0878(3) 0.1997(3) 0.0577(8) Uani 0.763(5) 1 d . . P A 1
H20 H 0.7981 0.0558 0.1267 0.069 Uiso 0.763(5) 1 calc R . P A 1
C20A C 0.9309(15) 0.1395(12) 0.2706(10) 0.0577(8) Uani 0.237(5) 1 d . . P A 2
H20A H 1.0168 0.2069 0.3288 0.069 Uiso 0.237(5) 1 calc R . P A 2
C21 C 1.0081(6) 0.1630(5) 0.2229(4) 0.0766(13) Uani 0.763(5) 1 d . . P A 1
H21 H 1.0570 0.1929 0.2979 0.092 Uiso 0.763(5) 1 calc R . P A 1
C21A C 0.9429(18) 0.1164(18) 0.1678(15) 0.0766(13) Uani 0.237(5) 1 d D . P A 2
H21A H 0.8485 0.0441 0.1197 0.092 Uiso 0.237(5) 1 calc R . P A 2
C22 C 1.0428(9) 0.1886(9) 0.0365(6) 0.097(2) Uani 0.763(5) 1 d . U P A 1
H22A H 0.9524 0.0939 0.0032 0.117 Uiso 0.763(5) 1 calc R . P A 1
H22B H 1.1218 0.1929 -0.0090 0.117 Uiso 0.763(5) 1 calc R . P A 1
C22A C 0.986(4) 0.170(3) 0.000(2) 0.097(2) Uani 0.237(5) 1 d . . P A 2
H22C H 1.0328 0.1392 -0.0615 0.117 Uiso 0.237(5) 1 calc R . P A 2
H22D H 0.8725 0.1129 -0.0195 0.117 Uiso 0.237(5) 1 calc R . P A 2
C23 C 0.9899(11) 0.3085(14) 0.0327(16) 0.106(2) Uani 0.763(5) 1 d . U P A 1
H23A H 0.9606 0.3011 -0.0447 0.127 Uiso 0.763(5) 1 calc R . P A 1
H23B H 0.8999 0.2971 0.0680 0.127 Uiso 0.763(5) 1 calc R . P A 1
C23A C 1.032(4) 0.315(5) 0.034(6) 0.106(2) Uani 0.237(5) 1 d D . P A 2
H23C H 0.9709 0.3284 0.0911 0.127 Uiso 0.237(5) 1 calc R . P A 2
H23D H 0.9849 0.3271 -0.0300 0.127 Uiso 0.237(5) 1 calc R . P A 2
C24 C 1.1295(9) 0.4523(9) 0.0960(7) 0.116(2) Uani 0.763(5) 1 d . U P A 1
H24A H 1.0977 0.5285 0.1038 0.139 Uiso 0.763(5) 1 calc R . P A 1
H24B H 1.2115 0.4686 0.0523 0.139 Uiso 0.763(5) 1 calc R . P A 1
C24A C 1.188(3) 0.451(3) 0.080(3) 0.116(2) Uani 0.237(5) 1 d D . P A 2
H24C H 1.2625 0.4472 0.0316 0.139 Uiso 0.237(5) 1 calc R . P A 2
H24D H 1.1741 0.5364 0.0867 0.139 Uiso 0.237(5) 1 calc R . P A 2
C25 C 1.1976(11) 0.4627(10) 0.2129(8) 0.120(2) Uani 0.763(5) 1 d . U P A 1
H25A H 1.2900 0.5558 0.2475 0.144 Uiso 0.763(5) 1 calc R . P A 1
H25B H 1.1199 0.4580 0.2596 0.144 Uiso 0.763(5) 1 calc R . P A 1
C25A C 1.242(4) 0.448(3) 0.193(3) 0.120(2) Uani 0.237(5) 1 d D . P A 2
H25C H 1.1724 0.4582 0.2439 0.144 Uiso 0.237(5) 1 calc R . P A 2
H25D H 1.3495 0.5213 0.2277 0.144 Uiso 0.237(5) 1 calc R . P A 2
C26 C 1.2431(9) 0.3436(8) 0.2091(6) 0.113(2) Uani 0.763(5) 1 d . U P A 1
H26A H 1.3296 0.3541 0.1700 0.135 Uiso 0.763(5) 1 calc R . P A 1
H26B H 1.2779 0.3496 0.2851 0.135 Uiso 0.763(5) 1 calc R . P A 1
C26A C 1.228(3) 0.297(3) 0.156(2) 0.113(2) Uani 0.237(5) 1 d D . P A 2
H26C H 1.2762 0.2836 0.2194 0.135 Uiso 0.237(5) 1 calc R . P A 2
H26D H 1.2898 0.2893 0.0980 0.135 Uiso 0.237(5) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.227(3) . ?
O2 N3 1.229(4) . ?
O3 N3 1.242(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.348(3) . ?
N1 C4 1.399(3) . ?
N2 C9 1.461(3) . ?
N2 C10 1.464(3) . ?
N2 C17 1.328(3) . ?
N3 C18 1.439(3) . ?
N4 C21 1.386(8) . ?
N4 C22 1.468(8) . ?
N4 C26 1.448(9) . ?
N4A C21A 1.38(3) . ?
N4A C22A 1.49(3) . ?
N4A C26A 1.57(4) . ?
C1 C2 1.537(3) . ?
C2 C3 1.502(3) . ?
C2 C9 1.545(3) . ?
C2 C19 1.578(3) . ?
C3 C4 1.400(3) . ?
C3 C8 1.378(4) . ?
C4 C5 1.373(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C9 C12 1.504(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.493(4) . ?
C11 C12 1.383(3) . ?
C11 C16 1.390(4) . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.347(4) . ?
C18 C19 1.483(4) . ?
C19 H19 0.94(3) . ?
C19 C20 1.550(4) . ?
C19 C20A 1.540(12) . ?
C20 H20 0.9300 . ?
C20 C21 1.300(6) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.27(2) . ?
C21 H21 0.9300 . ?
C21A H21A 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.581(18) . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C23A 1.36(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.505(10) . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C23A C24A 1.51(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.528(9) . ?
C24A H24C 0.9700 . ?
C24A H24D 0.9700 . ?
C24A C25A 1.50(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.508(10) . ?
C25A H25C 0.9700 . ?
C25A H25D 0.9700 . ?
C25A C26A 1.513(19) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26A H26C 0.9700 . ?
C26A H26D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 124.0 . . ?
C1 N1 C4 111.99(19) . . ?
C4 N1 H1 124.0 . . ?
C9 N2 C10 113.92(19) . . ?
C17 N2 C9 118.9(2) . . ?
C17 N2 C10 127.2(2) . . ?
O2 N3 O3 123.3(3) . . ?
O2 N3 C18 119.6(3) . . ?
O3 N3 C18 117.1(3) . . ?
C21 N4 C22 120.1(5) . . ?
C21 N4 C26 110.8(5) . . ?
C26 N4 C22 113.5(6) . . ?
C21A N4A C22A 111(2) . . ?
C21A N4A C26A 128(2) . . ?
C22A N4A C26A 111(2) . . ?
O1 C1 N1 126.6(2) . . ?
O1 C1 C2 125.20(19) . . ?
N1 C1 C2 108.2(2) . . ?
C1 C2 C9 109.78(18) . . ?
C1 C2 C19 107.18(19) . . ?
C3 C2 C1 102.06(17) . . ?
C3 C2 C9 114.53(18) . . ?
C3 C2 C19 115.52(19) . . ?
C9 C2 C19 107.37(17) . . ?
C4 C3 C2 108.6(2) . . ?
C8 C3 C2 132.4(2) . . ?
C8 C3 C4 118.9(2) . . ?
C3 C4 N1 109.1(2) . . ?
C5 C4 N1 128.1(2) . . ?
C5 C4 C3 122.8(2) . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.7(2) . . ?
C6 C5 H5 121.1 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 118.5(2) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N2 C9 C2 109.31(17) . . ?
N2 C9 H9 108.1 . . ?
N2 C9 C12 102.10(17) . . ?
C2 C9 H9 108.1 . . ?
C12 C9 C2 120.44(17) . . ?
C12 C9 H9 108.1 . . ?
N2 C10 H10A 111.4 . . ?
N2 C10 H10B 111.4 . . ?
N2 C10 C11 101.83(19) . . ?
H10A C10 H10B 109.3 . . ?
C11 C10 H10A 111.4 . . ?
C11 C10 H10B 111.4 . . ?
C12 C11 C10 111.6(2) . . ?
C12 C11 C16 120.3(3) . . ?
C16 C11 C10 128.1(3) . . ?
C11 C12 C9 110.2(2) . . ?
C13 C12 C9 129.3(2) . . ?
C13 C12 C11 120.3(2) . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 120.5 . . ?
C15 C16 C11 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
N2 C17 H17 119.4 . . ?
N2 C17 C18 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
N3 C18 C19 118.5(3) . . ?
C17 C18 N3 116.7(3) . . ?
C17 C18 C19 124.7(2) . . ?
C2 C19 H19 102.6(19) . . ?
C18 C19 C2 110.0(2) . . ?
C18 C19 H19 111.0(19) . . ?
C18 C19 C20 107.6(2) . . ?
C18 C19 C20A 135.3(5) . . ?
C20 C19 C2 109.2(2) . . ?
C20 C19 H19 116.4(19) . . ?
C20A C19 C2 108.3(4) . . ?
C20A C19 H19 81.8(19) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.1(4) . . ?
C21 C20 H20 120.4 . . ?
C19 C20A H20A 121.1 . . ?
C21A C20A C19 117.7(12) . . ?
C21A C20A H20A 121.1 . . ?
N4 C21 H21 115.7 . . ?
C20 C21 N4 128.7(5) . . ?
C20 C21 H21 115.7 . . ?
N4A C21A H21A 111.1 . . ?
C20A C21A N4A 137.7(18) . . ?
C20A C21A H21A 111.1 . . ?
N4 C22 H22A 108.9 . . ?
N4 C22 H22B 108.9 . . ?
N4 C22 C23 113.5(9) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
N4A C22A H22C 112.4 . . ?
N4A C22A H22D 112.4 . . ?
H22C C22A H22D 110.0 . . ?
C23A C22A N4A 97(4) . . ?
C23A C22A H22C 112.4 . . ?
C23A C22A H22D 112.4 . . ?
C22 C23 H23A 110.5 . . ?
C22 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
C24 C23 C22 106.3(9) . . ?
C24 C23 H23A 110.5 . . ?
C24 C23 H23B 110.5 . . ?
C22A C23A H23C 103.3 . . ?
C22A C23A H23D 103.3 . . ?
C22A C23A C24A 135(4) . . ?
H23C C23A H23D 105.2 . . ?
C24A C23A H23C 103.3 . . ?
C24A C23A H23D 103.3 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C23 C24 C25 113.3(10) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C23A C24A H24C 111.2 . . ?
C23A C24A H24D 111.2 . . ?
H24C C24A H24D 109.1 . . ?
C25A C24A C23A 103(4) . . ?
C25A C24A H24C 111.2 . . ?
C25A C24A H24D 111.2 . . ?
C24 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.5(7) . . ?
C26 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C24A C25A H25C 112.1 . . ?
C24A C25A H25D 112.1 . . ?
C24A C25A C26A 98(2) . . ?
H25C C25A H25D 109.7 . . ?
C26A C25A H25C 112.1 . . ?
C26A C25A H25D 112.1 . . ?
N4 C26 C25 109.2(7) . . ?
N4 C26 H26A 109.8 . . ?
N4 C26 H26B 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
N4A C26A H26C 108.2 . . ?
N4A C26A H26D 108.2 . . ?
C25A C26A N4A 116(3) . . ?
C25A C26A H26C 108.2 . . ?
C25A C26A H26D 108.2 . . ?
H26C C26A H26D 107.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.05 2.890(2) 165.2 2_766

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.7(2) . . . . ?
O1 C1 C2 C9 57.8(3) . . . . ?
O1 C1 C2 C19 -58.5(3) . . . . ?
O2 N3 C18 C17 18.0(4) . . . . ?
O2 N3 C18 C19 -164.8(3) . . . . ?
O3 N3 C18 C17 -160.2(2) . . . . ?
O3 N3 C18 C19 17.1(4) . . . . ?
N1 C1 C2 C3 -1.0(2) . . . . ?
N1 C1 C2 C9 -122.9(2) . . . . ?
N1 C1 C2 C19 120.8(2) . . . . ?
N1 C4 C5 C6 179.1(2) . . . . ?
N2 C9 C12 C11 6.4(2) . . . . ?
N2 C9 C12 C13 -178.7(2) . . . . ?
N2 C10 C11 C12 0.7(3) . . . . ?
N2 C10 C11 C16 -177.2(3) . . . . ?
N2 C17 C18 N3 165.4(2) . . . . ?
N2 C17 C18 C19 -11.6(4) . . . . ?
N3 C18 C19 C2 175.6(2) . . . . ?
N3 C18 C19 C20 56.7(3) . . . . ?
N3 C18 C19 C20A 28.1(8) . . . . ?
N4 C22 C23 C24 52.7(12) . . . . ?
N4A C22A C23A C24A 58(8) . . . . ?
C1 N1 C4 C3 0.6(3) . . . . ?
C1 N1 C4 C5 -178.9(2) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C1 C2 C3 C8 179.1(3) . . . . ?
C1 C2 C9 N2 -176.54(16) . . . . ?
C1 C2 C9 C12 65.8(2) . . . . ?
C1 C2 C19 C18 159.5(2) . . . . ?
C1 C2 C19 C20 -82.6(3) . . . . ?
C1 C2 C19 C20A -44.0(6) . . . . ?
C2 C3 C4 N1 -1.3(2) . . . . ?
C2 C3 C4 C5 178.3(2) . . . . ?
C2 C3 C8 C7 -177.3(3) . . . . ?
C2 C9 C12 C11 127.6(2) . . . . ?
C2 C9 C12 C13 -57.5(3) . . . . ?
C2 C19 C20 C21 102.3(4) . . . . ?
C2 C19 C20A C21A -106.4(11) . . . . ?
C3 C2 C9 N2 69.4(2) . . . . ?
C3 C2 C9 C12 -48.3(3) . . . . ?
C3 C2 C19 C18 -87.6(2) . . . . ?
C3 C2 C19 C20 30.3(3) . . . . ?
C3 C2 C19 C20A 68.9(6) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 N1 C1 O1 179.6(2) . . . . ?
C4 N1 C1 C2 0.3(3) . . . . ?
C4 C3 C8 C7 0.3(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C6 C7 C8 C3 -0.6(5) . . . . ?
C8 C3 C4 N1 -179.4(2) . . . . ?
C8 C3 C4 C5 0.1(4) . . . . ?
C9 N2 C10 C11 3.7(3) . . . . ?
C9 N2 C17 C18 -8.8(3) . . . . ?
C9 C2 C3 C4 119.9(2) . . . . ?
C9 C2 C3 C8 -62.4(3) . . . . ?
C9 C2 C19 C18 41.6(3) . . . . ?
C9 C2 C19 C20 159.5(2) . . . . ?
C9 C2 C19 C20A -161.9(5) . . . . ?
C9 C12 C13 C14 -173.3(2) . . . . ?
C10 N2 C9 C2 -134.8(2) . . . . ?
C10 N2 C9 C12 -6.2(2) . . . . ?
C10 N2 C17 C18 171.8(2) . . . . ?
C10 C11 C12 C9 -4.6(3) . . . . ?
C10 C11 C12 C13 180.0(2) . . . . ?
C10 C11 C16 C15 178.8(3) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
C14 C15 C16 C11 0.5(5) . . . . ?
C16 C11 C12 C9 173.4(2) . . . . ?
C16 C11 C12 C13 -2.0(4) . . . . ?
C17 N2 C9 C2 45.7(3) . . . . ?
C17 N2 C9 C12 174.38(19) . . . . ?
C17 N2 C10 C11 -176.9(2) . . . . ?
C17 C18 C19 C2 -7.4(4) . . . . ?
C17 C18 C19 C20 -126.3(3) . . . . ?
C17 C18 C19 C20A -154.9(7) . . . . ?
C18 C19 C20 C21 -138.3(3) . . . . ?
C18 C19 C20A C21A 41.4(14) . . . . ?
C19 C2 C3 C4 -114.6(2) . . . . ?
C19 C2 C3 C8 63.2(3) . . . . ?
C19 C2 C9 N2 -60.3(2) . . . . ?
C19 C2 C9 C12 -178.0(2) . . . . ?
C19 C20 C21 N4 178.7(5) . . . . ?
C19 C20A C21A N4A 178(2) . . . . ?
C21 N4 C22 C23 76.5(9) . . . . ?
C21 N4 C26 C25 -81.8(6) . . . . ?
C21A N4A C22A C23A 103(3) . . . . ?
C21A N4A C26A C25A -75(3) . . . . ?
C22 N4 C21 C20 12.0(9) . . . . ?
C22 N4 C26 C25 56.8(8) . . . . ?
C22 C23 C24 C25 -51.5(12) . . . . ?
C22A N4A C21A C20A -145(2) . . . . ?
C22A N4A C26A C25A 67(3) . . . . ?
C22A C23A C24A C25A -68(8) . . . . ?
C23 C24 C25 C26 55.9(10) . . . . ?
C23A C24A C25A C26A 53(3) . . . . ?
C24 C25 C26 N4 -55.1(7) . . . . ?
C24A C25A C26A N4A -67(3) . . . . ?
C26 N4 C21 C20 147.5(5) . . . . ?
C26 N4 C22 C23 -57.9(8) . . . . ?
C26A N4A C21A C20A -4(4) . . . . ?
C26A N4A C22A C23A -45(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.883
####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2071226'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2019-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 N2 O5'
_chemical_formula_sum            'C26 H24 N2 O5'
_chemical_formula_weight         444.47
_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   15.5191(7)
_cell_length_b                   9.0804(5)
_cell_length_c                   30.9354(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4359.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1065 before and 0.0774 after correction. The Ratio of minimum to maximum transmission is 0.8679. 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    1.354
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            24240
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.599
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2370
_reflns_number_total             4463
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.037
_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)+(0.0442P)²+0.8235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1364
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.63221(18) 0.3613(3) 0.28830(8) 0.0341(7) Uani 1 1 d . . . . .
H1 H 0.6113 0.4231 0.3107 0.041 Uiso 1 1 calc R . . . .
C2 C 0.62019(19) 0.4009(3) 0.24526(8) 0.0410(8) Uani 1 1 d . . . . .
H2 H 0.5895 0.4883 0.2384 0.049 Uiso 1 1 calc R . . . .
C3 C 0.6527(2) 0.3138(4) 0.21264(9) 0.0524(9) Uani 1 1 d . . . . .
H3 H 0.6451 0.3421 0.1833 0.063 Uiso 1 1 calc R . . . .
C4 C 0.6962(2) 0.1852(4) 0.22257(9) 0.0526(9) Uani 1 1 d . . . . .
H4 H 0.7190 0.1256 0.2001 0.063 Uiso 1 1 calc R . . . .
C5 C 0.70638(19) 0.1436(3) 0.26525(8) 0.0419(8) Uani 1 1 d . . . . .
H5 H 0.7352 0.0542 0.2720 0.050 Uiso 1 1 calc R . . . .
C6 C 0.67473(17) 0.2315(3) 0.29845(8) 0.0298(7) Uani 1 1 d . . . . .
C7 C 0.68904(17) 0.1800(3) 0.34394(8) 0.0281(6) Uani 1 1 d . . . . .
C8 C 0.65595(17) 0.2720(3) 0.38109(7) 0.0256(6) Uani 1 1 d . . . . .
H8 H 0.6712 0.3774 0.3757 0.031 Uiso 1 1 calc R . . . .
C9 C 0.69513(17) 0.2239(3) 0.42464(7) 0.0279(6) Uani 1 1 d . . . . .
H9 H 0.6810 0.1180 0.4299 0.033 Uiso 1 1 calc R . . . .
C10 C 0.79033(18) 0.2488(3) 0.43327(8) 0.0299(7) Uani 1 1 d . . . . .
C11 C 0.86188(18) 0.1978(3) 0.41086(9) 0.0348(7) Uani 1 1 d . . . . .
H11 H 0.8550 0.1444 0.3847 0.042 Uiso 1 1 calc R . . . .
C12 C 0.9438(2) 0.2259(3) 0.42723(9) 0.0395(7) Uani 1 1 d . . . . .
H12 H 0.9930 0.1914 0.4121 0.047 Uiso 1 1 calc R . . . .
C13 C 0.9542(2) 0.3033(3) 0.46520(9) 0.0406(8) Uani 1 1 d . . . . .
H13 H 1.0106 0.3221 0.4758 0.049 Uiso 1 1 calc R . . . .
C14 C 0.88388(19) 0.3535(3) 0.48782(9) 0.0403(8) Uani 1 1 d . . . . .
H14 H 0.8913 0.4071 0.5139 0.048 Uiso 1 1 calc R . . . .
C15 C 0.80192(18) 0.3250(3) 0.47197(8) 0.0334(7) Uani 1 1 d . . . . .
C16 C 0.71770(18) 0.3636(3) 0.49239(8) 0.0402(8) Uani 1 1 d . . . . .
H16A H 0.7093 0.3101 0.5199 0.048 Uiso 1 1 calc R . . . .
H16B H 0.7131 0.4708 0.4977 0.048 Uiso 1 1 calc R . . . .
C17 C 0.57545(17) 0.3642(3) 0.45670(8) 0.0305(7) Uani 1 1 d . . . . .
H17 H 0.5534 0.4228 0.4796 0.037 Uiso 1 1 calc R . . . .
C18 C 0.52387(17) 0.3338(3) 0.42243(8) 0.0276(6) Uani 1 1 d . . . . .
C19 C 0.55526(17) 0.2569(3) 0.38244(7) 0.0266(6) Uani 1 1 d . . . . .
H19 H 0.5316 0.3111 0.3569 0.032 Uiso 1 1 calc R . . . .
C20 C 0.52480(17) 0.1003(3) 0.37951(8) 0.0301(7) Uani 1 1 d . . . . .
H20 H 0.5357 0.0376 0.4035 0.036 Uiso 1 1 calc R . . . .
C21 C 0.48399(17) 0.0435(3) 0.34608(8) 0.0337(7) Uani 1 1 d . . . . .
H21 H 0.4750 0.1049 0.3216 0.040 Uiso 1 1 calc R . . . .
C22 C 0.3225(2) -0.0471(4) 0.39146(10) 0.0543(9) Uani 1 1 d . . . . .
H22A H 0.3304 -0.0674 0.4223 0.082 Uiso 1 1 calc GR . . . .
H22B H 0.2620 -0.0620 0.3837 0.082 Uiso 1 1 calc GR . . . .
H22C H 0.3390 0.0550 0.3854 0.082 Uiso 1 1 calc GR . . . .
C23 C 0.3777(2) -0.1488(4) 0.36564(9) 0.0424(8) Uani 1 1 d . . . . .
C24 C 0.45120(19) -0.1096(3) 0.34407(8) 0.0356(7) Uani 1 1 d . . . . .
C25 C 0.4988(2) -0.2195(4) 0.32036(9) 0.0460(8) Uani 1 1 d . . . . .
C26 C 0.5780(2) -0.1756(4) 0.29600(10) 0.0576(10) Uani 1 1 d . . . . .
H26A H 0.5985 -0.2594 0.2789 0.086 Uiso 1 1 calc GR . . . .
H26B H 0.6229 -0.1456 0.3164 0.086 Uiso 1 1 calc GR . . . .
H26C H 0.5644 -0.0933 0.2767 0.086 Uiso 1 1 calc GR . . . .
N1 N 0.65565(14) 0.3147(2) 0.45927(6) 0.0307(6) Uani 1 1 d . . . . .
N2 N 0.43876(15) 0.3860(3) 0.42295(7) 0.0337(6) Uani 1 1 d . . . . .
O1 O 0.72464(12) 0.0623(2) 0.35086(5) 0.0391(5) Uani 1 1 d . . . . .
O2 O 0.41049(12) 0.4551(2) 0.45497(6) 0.0420(5) Uani 1 1 d . . . . .
O3 O 0.39207(12) 0.3586(2) 0.39125(6) 0.0459(6) Uani 1 1 d . . . . .
O4 O 0.34920(15) -0.2875(2) 0.36647(7) 0.0592(7) Uani 1 1 d . . . . .
H4A H 0.3821 -0.3410 0.3517 0.089 Uiso 1 1 calc GR . . . .
O5 O 0.47664(15) -0.3530(2) 0.32043(7) 0.0619(7) 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 H1 0.9500 . ?
C1 C2 1.392(3) . ?
C1 C6 1.387(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C6 C7 1.499(3) . ?
C7 C8 1.510(3) . ?
C7 O1 1.222(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.541(3) . ?
C8 C19 1.569(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.518(4) . ?
C9 N1 1.484(3) . ?
C10 C11 1.389(4) . ?
C10 C15 1.395(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(4) . ?
C15 C16 1.493(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N1 1.474(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.357(3) . ?
C17 N1 1.326(3) . ?
C18 C19 1.502(3) . ?
C18 N2 1.403(3) . ?
C19 H19 1.0000 . ?
C19 C20 1.502(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.318(3) . ?
C21 H21 0.9500 . ?
C21 C24 1.482(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C23 1.492(4) . ?
C23 C24 1.368(4) . ?
C23 O4 1.335(3) . ?
C24 C25 1.442(4) . ?
C25 C26 1.496(4) . ?
C25 O5 1.259(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N2 O2 1.252(2) . ?
N2 O3 1.244(3) . ?
O4 H4A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.0(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 123.2(2) . . ?
C5 C6 C7 117.5(2) . . ?
C6 C7 C8 119.5(2) . . ?
O1 C7 C6 120.3(2) . . ?
O1 C7 C8 120.2(2) . . ?
C7 C8 H8 108.8 . . ?
C7 C8 C9 112.0(2) . . ?
C7 C8 C19 108.1(2) . . ?
C9 C8 H8 108.8 . . ?
C9 C8 C19 110.18(19) . . ?
C19 C8 H8 108.8 . . ?
C8 C9 H9 109.1 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 109.1 . . ?
N1 C9 C8 108.1(2) . . ?
N1 C9 H9 109.1 . . ?
N1 C9 C10 101.1(2) . . ?
C11 C10 C9 129.9(2) . . ?
C11 C10 C15 119.4(3) . . ?
C15 C10 C9 110.5(2) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.1(3) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C16 111.5(2) . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 C16 127.5(2) . . ?
C15 C16 H16A 111.4 . . ?
C15 C16 H16B 111.4 . . ?
H16A C16 H16B 109.2 . . ?
N1 C16 C15 102.0(2) . . ?
N1 C16 H16A 111.4 . . ?
N1 C16 H16B 111.4 . . ?
C18 C17 H17 118.9 . . ?
N1 C17 H17 118.9 . . ?
N1 C17 C18 122.1(2) . . ?
C17 C18 C19 123.1(2) . . ?
C17 C18 N2 118.5(2) . . ?
N2 C18 C19 118.1(2) . . ?
C8 C19 H19 107.6 . . ?
C18 C19 C8 107.7(2) . . ?
C18 C19 H19 107.6 . . ?
C18 C19 C20 112.8(2) . . ?
C20 C19 C8 113.2(2) . . ?
C20 C19 H19 107.6 . . ?
C19 C20 H20 117.7 . . ?
C21 C20 C19 124.7(2) . . ?
C21 C20 H20 117.7 . . ?
C20 C21 H21 117.8 . . ?
C20 C21 C24 124.4(3) . . ?
C24 C21 H21 117.8 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
C24 C23 C22 125.3(3) . . ?
O4 C23 C22 112.6(3) . . ?
O4 C23 C24 122.1(3) . . ?
C23 C24 C21 120.7(3) . . ?
C23 C24 C25 119.6(3) . . ?
C25 C24 C21 119.7(3) . . ?
C24 C25 C26 119.5(3) . . ?
O5 C25 C24 121.7(3) . . ?
O5 C25 C26 118.8(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 . . ?
C16 N1 C9 113.5(2) . . ?
C17 N1 C9 122.2(2) . . ?
C17 N1 C16 123.6(2) . . ?
O2 N2 C18 120.5(2) . . ?
O3 N2 C18 118.1(2) . . ?
O3 N2 O2 121.3(2) . . ?
C23 O4 H4A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O5 0.84 1.76 2.509(3) 147.3 .

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
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C6 C7 C8 0.1(4) . . . . ?
C1 C6 C7 O1 177.7(3) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
C2 C1 C6 C7 -179.1(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -179.3(3) . . . . ?
C5 C6 C7 C8 179.9(2) . . . . ?
C5 C6 C7 O1 -2.5(4) . . . . ?
C6 C1 C2 C3 -1.9(4) . . . . ?
C6 C7 C8 C9 -165.9(2) . . . . ?
C6 C7 C8 C19 72.5(3) . . . . ?
C7 C8 C9 C10 68.1(3) . . . . ?
C7 C8 C9 N1 -177.1(2) . . . . ?
C7 C8 C19 C18 173.4(2) . . . . ?
C7 C8 C19 C20 48.0(3) . . . . ?
C8 C9 C10 C11 -58.9(4) . . . . ?
C8 C9 C10 C15 126.8(2) . . . . ?
C8 C9 N1 C16 -138.8(2) . . . . ?
C8 C9 N1 C17 31.7(3) . . . . ?
C8 C19 C20 C21 -110.7(3) . . . . ?
C9 C8 C19 C18 50.7(3) . . . . ?
C9 C8 C19 C20 -74.7(3) . . . . ?
C9 C10 C11 C12 -174.8(2) . . . . ?
C9 C10 C15 C14 176.5(2) . . . . ?
C9 C10 C15 C16 -2.0(3) . . . . ?
C10 C9 N1 C16 -12.3(3) . . . . ?
C10 C9 N1 C17 158.2(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C10 C15 C16 N1 -5.4(3) . . . . ?
C11 C10 C15 C14 1.5(4) . . . . ?
C11 C10 C15 C16 -176.9(2) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C10 -1.1(4) . . . . ?
C13 C14 C15 C16 177.1(3) . . . . ?
C14 C15 C16 N1 176.3(3) . . . . ?
C15 C10 C11 C12 -1.0(4) . . . . ?
C15 C16 N1 C9 11.3(3) . . . . ?
C15 C16 N1 C17 -159.1(2) . . . . ?
C17 C18 C19 C8 -19.6(3) . . . . ?
C17 C18 C19 C20 106.1(3) . . . . ?
C17 C18 N2 O2 -2.2(4) . . . . ?
C17 C18 N2 O3 179.4(2) . . . . ?
C18 C17 N1 C9 0.7(4) . . . . ?
C18 C17 N1 C16 170.3(2) . . . . ?
C18 C19 C20 C21 126.6(3) . . . . ?
C19 C8 C9 C10 -171.6(2) . . . . ?
C19 C8 C9 N1 -56.7(3) . . . . ?
C19 C18 N2 O2 -177.6(2) . . . . ?
C19 C18 N2 O3 4.0(4) . . . . ?
C19 C20 C21 C24 -177.6(2) . . . . ?
C20 C21 C24 C23 76.3(4) . . . . ?
C20 C21 C24 C25 -101.6(3) . . . . ?
C21 C24 C25 C26 -3.5(4) . . . . ?
C21 C24 C25 O5 174.8(3) . . . . ?
C22 C23 C24 C21 1.9(4) . . . . ?
C22 C23 C24 C25 179.8(3) . . . . ?
C23 C24 C25 C26 178.6(3) . . . . ?
C23 C24 C25 O5 -3.1(4) . . . . ?
N1 C9 C10 C11 -177.4(3) . . . . ?
N1 C9 C10 C15 8.3(3) . . . . ?
N1 C17 C18 C19 -7.1(4) . . . . ?
N1 C17 C18 N2 177.7(2) . . . . ?
N2 C18 C19 C8 155.6(2) . . . . ?
N2 C18 C19 C20 -78.7(3) . . . . ?
O1 C7 C8 C9 16.5(4) . . . . ?
O1 C7 C8 C19 -105.0(3) . . . . ?
O4 C23 C24 C21 -176.2(3) . . . . ?
O4 C23 C24 C25 1.7(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
