# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_210418zbl2_0m
_database_code_depnum_ccdc_archive 'CCDC 2079618'
loop_
_audit_author_name
_audit_author_address
'shuxin cui'
;mdjnenu
China
;
_audit_update_record             
;
2021-11-28 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 N4, C10 H4.58 O8, C10 H5 O8'
_chemical_formula_sum            'C46 H29.58 N4 O16'
_chemical_formula_weight         894.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.7493(16)
_cell_length_b                   14.816(2)
_cell_length_c                   14.827(2)
_cell_angle_alpha                81.262(3)
_cell_angle_beta                 81.825(3)
_cell_angle_gamma                72.098(3)
_cell_volume                     2003.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2899
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.890
_cell_measurement_theta_min      2.489
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0318 after correction.
The Ratio of minimum to maximum transmission is 0.8993.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             923.2
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12029
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.434
_diffrn_reflns_theta_min         1.454
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4878
_reflns_number_total             9154
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         8641
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0910
_refine_ls_restrained_S_all      1.038
_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)+(0.1424P)²+2.2738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2500
_refine_ls_wR_factor_ref         0.2980
_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. Restrained distances
 O7-H7A
 0.82 with sigma of 0.02
 O14-H14
 0.82 with sigma of 0.02
3. Rigid bond restraints
 O14, C43
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(N4) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Sof(O2A)=Sof(O1A)=1-FVAR(1)
 Sof(O2)=Sof(O1)=Sof(H1)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C19(H19A,H19B)
6.b Aromatic/amide H refined with riding coordinates:
 C46(H46), C41(H41), C31(H31), C36(H36), C13(H13), C12(H12), C10(H10),
 C18(H18), C7(H7), C9(H9), C15(H15), C17(H17), C16(H16), C3(H3), C5(H5),
 C26(H26), C21(H21), C23(H23), C4(H4), C22(H22)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.6918(3) 0.6088(2) 0.2145(2) 0.0564(8) Uani 1 1 d . . . . .
O6 O 0.4662(3) 0.6472(2) 0.1807(2) 0.0613(10) Uani 1 1 d . . . . .
O4 O 0.8322(3) 0.5187(3) 0.3905(2) 0.0621(9) Uani 1 1 d . . . . .
O10 O 0.5349(4) 0.7779(2) 0.0577(2) 0.0653(9) Uani 1 1 d . . . . .
O15 O 0.0824(3) 1.0229(3) -0.1422(2) 0.0698(10) Uani 1 1 d . . . . .
O16 O 0.1327(4) 0.8857(3) -0.0593(3) 0.0749(11) Uani 1 1 d . . . . .
N2 N 1.0159(4) 0.2746(2) 0.8098(3) 0.0490(9) Uani 1 1 d . . . . .
O7 O 0.1074(3) 0.5237(3) 0.3649(3) 0.0811(12) Uani 1 1 d D . . . .
O9 O 0.3269(4) 0.7803(3) 0.0180(3) 0.0799(12) Uani 1 1 d . . . . .
O8 O 0.1755(4) 0.3730(3) 0.4301(3) 0.0858(13) Uani 1 1 d . . . . .
O3 O 0.8814(4) 0.4096(3) 0.2943(3) 0.0812(11) Uani 1 1 d . . . . .
C39 C 0.3275(3) 0.9572(2) -0.1112(2) 0.0316(8) Uani 1 1 d . . . . .
O11 O 0.8142(4) 1.0010(4) -0.1021(3) 0.0886(14) Uani 1 1 d . . . . .
C44 C 0.6072(3) 0.9805(3) -0.1469(2) 0.0335(8) Uani 1 1 d . . . . .
C38 C 0.4409(4) 0.8972(2) -0.0610(2) 0.0325(8) Uani 1 1 d . . . . .
C46 C 0.5769(4) 0.9120(3) -0.0790(2) 0.0342(8) Uani 1 1 d . . . . .
H46 H 0.650356 0.874473 -0.043961 0.041 Uiso 1 1 calc R U . . .
C42 C 0.4970(4) 1.0372(2) -0.1981(3) 0.0356(8) Uani 1 1 d . . . . .
C41 C 0.3596(4) 1.0256(3) -0.1785(3) 0.0359(8) Uani 1 1 d . . . . .
H41 H 0.285842 1.065536 -0.212015 0.043 Uiso 1 1 calc R U . . .
N3 N 0.8913(4) 0.1418(3) 0.4043(3) 0.0623(11) Uani 1 1 d . . . . .
C32 C 0.5321(4) 0.5292(3) 0.3042(3) 0.0348(8) Uani 1 1 d . . . . .
C31 C 0.3921(4) 0.5220(3) 0.3204(3) 0.0394(9) Uani 1 1 d . . . . .
H31 H 0.321250 0.563243 0.285436 0.047 Uiso 1 1 calc R U . . .
C29 C 0.3545(4) 0.4547(3) 0.3875(3) 0.0396(9) Uani 1 1 d . . . . .
O12 O 0.8213(4) 0.9818(4) -0.2450(3) 0.0976(15) Uani 1 1 d . . . . .
C33 C 0.5706(4) 0.6005(3) 0.2296(3) 0.0374(9) Uani 1 1 d . . . . .
C34 C 0.6377(4) 0.4693(3) 0.3580(3) 0.0399(9) Uani 1 1 d . . . . .
C28 C 0.4617(4) 0.3933(3) 0.4411(3) 0.0387(9) Uani 1 1 d . . . . .
C11 C 0.9651(4) 0.2247(3) 0.6491(3) 0.0432(10) Uani 1 1 d . . . . .
C37 C 0.4327(5) 0.8143(3) 0.0113(3) 0.0442(9) Uani 1 1 d . . . . .
C27 C 0.4406(4) 0.3144(3) 0.5144(3) 0.0440(10) Uani 1 1 d . . . . .
C36 C 0.6002(4) 0.4028(3) 0.4257(3) 0.0438(10) Uani 1 1 d . . . . .
H36 H 0.670618 0.363161 0.461836 0.053 Uiso 1 1 calc R U . . .
C40 C 0.1696(4) 0.9569(3) -0.1029(3) 0.0456(10) Uani 1 1 d . . . . .
C45 C 0.7594(4) 0.9863(3) -0.1690(3) 0.0434(9) Uani 1 1 d . . . . .
C14 C 0.9377(4) 0.1967(3) 0.5638(3) 0.0476(10) Uani 1 1 d . . . . .
C35 C 0.7969(4) 0.4663(3) 0.3431(3) 0.0506(11) Uani 1 1 d . . . . .
C43 C 0.5225(5) 1.1123(3) -0.2735(4) 0.0607(12) Uani 1 1 d . U . . .
C13 C 1.1132(5) 0.2727(3) 0.7357(4) 0.0573(12) Uani 1 1 d . . . . .
H13 H 1.197574 0.288215 0.739276 0.069 Uiso 1 1 calc R U . . .
O13 O 0.5932(6) 1.1617(4) -0.2682(3) 0.1170(18) Uani 1 1 d . . . . .
O14 O 0.4562(5) 1.1194(4) -0.3452(3) 0.120(2) Uani 1 1 d D U . . .
C12 C 1.0900(4) 0.2484(3) 0.6558(4) 0.0556(12) Uani 1 1 d . . . . .
H12 H 1.158385 0.247730 0.605096 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8657(4) 0.2277(3) 0.7268(3) 0.0559(12) Uani 1 1 d . . . . .
H10 H 0.780525 0.212465 0.725018 0.067 Uiso 1 1 calc R U . . .
C18 C 0.9757(5) 0.2399(4) 0.4782(4) 0.0595(13) Uani 1 1 d . . . . .
H18 H 1.017949 0.288973 0.473882 0.071 Uiso 1 1 calc R U . . .
C30 C 0.2028(5) 0.4478(4) 0.3965(4) 0.0603(13) Uani 1 1 d . . . . .
C7 C 0.9647(5) 0.4804(4) 0.8841(3) 0.0587(12) Uani 1 1 d . . . . .
H7 H 1.047721 0.479729 0.844335 0.070 Uiso 1 1 calc R U . . .
C9 C 0.8930(5) 0.2530(3) 0.8052(4) 0.0594(12) Uani 1 1 d . . . . .
H9 H 0.825561 0.255369 0.856593 0.071 Uiso 1 1 calc R U . . .
C6 C 0.9373(5) 0.3952(4) 0.9212(3) 0.0602(12) Uani 1 1 d . . . . .
C15 C 0.8742(5) 0.1254(3) 0.5659(3) 0.0582(12) Uani 1 1 d . . . . .
H15 H 0.845894 0.094987 0.621863 0.070 Uiso 1 1 calc R U . . .
C8 C 1.0423(5) 0.3013(4) 0.8976(3) 0.0628(13) Uani 1 1 d . . . . .
H8A H 1.140413 0.305598 0.892556 0.075 Uiso 1 1 calc R U . . .
H8B H 1.033250 0.251556 0.946859 0.075 Uiso 1 1 calc R U . . .
O2 O 0.5206(7) 0.2345(4) 0.5111(4) 0.0565(18) Uani 0.584(8) 1 d . . P A 1
C17 C 0.9518(5) 0.2112(4) 0.4008(4) 0.0670(14) Uani 1 1 d . . . . .
H17 H 0.978421 0.240894 0.344066 0.080 Uiso 1 1 calc R U . . .
O1 O 0.3504(5) 0.3352(3) 0.5883(3) 0.0491(17) Uani 0.584(8) 1 d . . P A 1
H1 H 0.289904 0.386866 0.577257 0.074 Uiso 0.584(8) 1 calc R U P A 1
C16 C 0.8525(6) 0.0988(4) 0.4853(4) 0.0686(14) Uani 1 1 d . . . . .
H16 H 0.810034 0.050182 0.487411 0.082 Uiso 1 1 calc R U . . .
C2 C 0.8680(6) 0.5669(4) 0.9065(4) 0.0696(14) Uani 1 1 d . . . . .
C20 C 0.7078(5) 0.1606(5) 0.2992(4) 0.0701(15) Uani 1 1 d . . . . .
C19 C 0.8612(6) 0.1137(5) 0.3177(4) 0.0812(17) Uani 1 1 d . . . . .
H19A H 0.924993 0.132088 0.266687 0.097 Uiso 1 1 calc R U . . .
H19B H 0.880881 0.044959 0.323262 0.097 Uiso 1 1 calc R U . . .
C1 C 0.8982(8) 0.6559(5) 0.8719(5) 0.093(2) Uani 1 1 d . . . . .
C3 C 0.7483(7) 0.5679(5) 0.9669(5) 0.099(2) Uani 1 1 d . . . . .
H3 H 0.684040 0.625799 0.981705 0.119 Uiso 1 1 calc R U . . .
C5 C 0.8173(7) 0.3975(5) 0.9839(5) 0.098(2) Uani 1 1 d . . . . .
H5 H 0.800481 0.340640 1.011285 0.118 Uiso 1 1 calc R U . . .
C26 C 0.6058(6) 0.1166(5) 0.3448(5) 0.093(2) Uani 1 1 d . . . . .
H26 H 0.636218 0.060077 0.383347 0.111 Uiso 1 1 calc R U . . .
C21 C 0.6680(8) 0.2413(5) 0.2429(5) 0.097(2) Uani 1 1 d . . . . .
H21 H 0.736103 0.271433 0.214278 0.116 Uiso 1 1 calc R U . . .
C23 C 0.4219(9) 0.2373(7) 0.2747(6) 0.110(3) Uani 1 1 d . . . . .
H23 H 0.324181 0.264354 0.266792 0.132 Uiso 1 1 calc R U . . .
C24 C 0.4624(7) 0.1550(6) 0.3338(6) 0.104(2) Uani 1 1 d . . . . .
N1 N 0.9139(10) 0.7293(5) 0.8468(5) 0.142(3) Uani 1 1 d . . . . .
C4 C 0.7220(8) 0.4835(6) 1.0063(6) 0.129(3) Uani 1 1 d . . . . .
H4 H 0.640547 0.484428 1.047656 0.155 Uiso 1 1 calc R U . . .
C22 C 0.5183(10) 0.2808(7) 0.2273(6) 0.118(3) Uani 1 1 d . . . . .
H22 H 0.488052 0.334844 0.185754 0.142 Uiso 1 1 calc R U . . .
N4 N 0.2813(10) 0.0758(6) 0.4432(6) 0.144(3) Uani 1 1 d . U . . .
O2A O 0.5305(10) 0.2804(8) 0.5645(8) 0.084(4) Uani 0.416(8) 1 d . . P A 2
C25 C 0.3555(9) 0.1140(6) 0.3877(7) 0.127(3) Uani 1 1 d . . . . .
O1A O 0.3407(9) 0.2748(6) 0.5052(6) 0.076(3) Uani 0.416(8) 1 d . . P A 2
H16A H 0.217(5) 0.833(3) -0.030(3) 0.053(12) Uiso 1 1 d . . . . .
H6 H 0.499(6) 0.689(4) 0.142(4) 0.083(17) Uiso 1 1 d . . . . .
H11 H 0.910(8) 1.013(5) -0.110(5) 0.12(2) Uiso 1 1 d . . . . .
H14 H 0.479(7) 1.157(4) -0.390(3) 0.11(2) Uiso 1 1 d D . . . .
H7A H 0.030(6) 0.513(7) 0.356(6) 0.17(4) Uiso 1 1 d 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
O5 C33 1.212(4) . ?
O6 C33 1.291(4) . ?
O6 H6 0.88(6) . ?
O4 C35 1.271(6) . ?
O10 C37 1.228(5) . ?
O15 C40 1.214(5) . ?
O16 C40 1.274(5) . ?
O16 H16A 1.04(5) . ?
N2 C13 1.342(6) . ?
N2 C9 1.346(5) . ?
N2 C8 1.494(6) . ?
O7 C30 1.292(6) . ?
O7 H7A 0.84(2) . ?
O9 C37 1.266(5) . ?
O9 H16A 1.34(5) . ?
O8 C30 1.233(5) . ?
O3 C35 1.223(6) . ?
C39 C38 1.412(5) . ?
C39 C41 1.387(5) . ?
C39 C40 1.528(5) . ?
O11 C45 1.267(5) . ?
O11 H11 1.00(7) . ?
C44 C46 1.385(5) . ?
C44 C42 1.386(5) . ?
C44 C45 1.500(5) . ?
C38 C46 1.392(5) . ?
C38 C37 1.517(5) . ?
C46 H46 0.9300 . ?
C42 C41 1.386(5) . ?
C42 C43 1.504(5) . ?
C41 H41 0.9300 . ?
N3 C17 1.325(6) . ?
N3 C16 1.334(7) . ?
N3 C19 1.501(7) . ?
C32 C31 1.387(5) . ?
C32 C33 1.499(5) . ?
C32 C34 1.394(5) . ?
C31 H31 0.9300 . ?
C31 C29 1.392(5) . ?
C29 C28 1.408(5) . ?
C29 C30 1.500(5) . ?
O12 C45 1.202(5) . ?
C34 C36 1.388(5) . ?
C34 C35 1.524(5) . ?
C28 C27 1.513(5) . ?
C28 C36 1.383(5) . ?
C11 C14 1.472(6) . ?
C11 C12 1.387(5) . ?
C11 C10 1.393(6) . ?
C27 O2 1.206(7) . ?
C27 O1 1.316(6) . ?
C27 O2A 1.172(10) . ?
C27 O1A 1.314(9) . ?
C36 H36 0.9300 . ?
C14 C18 1.387(6) . ?
C14 C15 1.374(6) . ?
C43 O13 1.167(6) . ?
C43 O14 1.295(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.356(7) . ?
O14 H14 0.86(2) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.357(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.355(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.386(7) . ?
C7 C2 1.392(7) . ?
C9 H9 0.9300 . ?
C6 C8 1.508(7) . ?
C6 C5 1.382(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C17 H17 0.9300 . ?
O1 H1 0.8200 . ?
C16 H16 0.9300 . ?
C2 C1 1.443(9) . ?
C2 C3 1.364(8) . ?
C20 C19 1.488(8) . ?
C20 C26 1.394(8) . ?
C20 C21 1.335(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C1 N1 1.143(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(11) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(10) . ?
C26 H26 0.9300 . ?
C26 C24 1.361(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.433(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(12) . ?
C23 C22 1.355(13) . ?
C24 C25 1.448(11) . ?
C4 H4 0.9300 . ?
C22 H22 0.9300 . ?
N4 C25 1.209(10) . ?

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
C33 O6 H6 106(4) . . ?
C40 O16 H16A 114(2) . . ?
C13 N2 C9 120.0(4) . . ?
C13 N2 C8 120.6(4) . . ?
C9 N2 C8 119.4(4) . . ?
C30 O7 H7A 113(7) . . ?
C37 O9 H16A 114.9(19) . . ?
C38 C39 C40 128.7(3) . . ?
C41 C39 C38 117.8(3) . . ?
C41 C39 C40 113.5(3) . . ?
C45 O11 H11 122(4) . . ?
C46 C44 C42 118.5(3) . . ?
C46 C44 C45 119.9(3) . . ?
C42 C44 C45 121.3(3) . . ?
C39 C38 C37 126.8(3) . . ?
C46 C38 C39 118.7(3) . . ?
C46 C38 C37 114.5(3) . . ?
C44 C46 C38 122.6(3) . . ?
C44 C46 H46 118.7 . . ?
C38 C46 H46 118.7 . . ?
C44 C42 C41 119.4(3) . . ?
C44 C42 C43 121.4(3) . . ?
C41 C42 C43 119.2(3) . . ?
C39 C41 H41 118.6 . . ?
C42 C41 C39 122.9(3) . . ?
C42 C41 H41 118.6 . . ?
C17 N3 C16 119.8(5) . . ?
C17 N3 C19 120.4(5) . . ?
C16 N3 C19 119.8(5) . . ?
C31 C32 C33 120.7(3) . . ?
C31 C32 C34 119.2(3) . . ?
C34 C32 C33 120.0(3) . . ?
C32 C31 H31 119.1 . . ?
C32 C31 C29 121.9(3) . . ?
C29 C31 H31 119.1 . . ?
C31 C29 C28 118.8(3) . . ?
C31 C29 C30 118.3(3) . . ?
C28 C29 C30 122.8(3) . . ?
O5 C33 O6 123.8(3) . . ?
O5 C33 C32 122.0(3) . . ?
O6 C33 C32 114.1(3) . . ?
C32 C34 C35 124.1(3) . . ?
C36 C34 C32 119.0(3) . . ?
C36 C34 C35 116.8(3) . . ?
C29 C28 C27 125.6(3) . . ?
C36 C28 C29 118.7(3) . . ?
C36 C28 C27 115.6(3) . . ?
C12 C11 C14 121.9(4) . . ?
C12 C11 C10 117.4(4) . . ?
C10 C11 C14 120.7(4) . . ?
O10 C37 O9 121.7(4) . . ?
O10 C37 C38 118.4(3) . . ?
O9 C37 C38 119.7(4) . . ?
O2 C27 C28 119.6(4) . . ?
O2 C27 O1 119.5(4) . . ?
O1 C27 C28 120.1(4) . . ?
O2A C27 C28 118.0(5) . . ?
O2A C27 O1A 123.1(7) . . ?
O1A C27 C28 117.2(5) . . ?
C34 C36 H36 118.9 . . ?
C28 C36 C34 122.3(3) . . ?
C28 C36 H36 118.9 . . ?
O15 C40 O16 120.9(4) . . ?
O15 C40 C39 119.2(4) . . ?
O16 C40 C39 119.8(4) . . ?
O11 C45 C44 114.5(3) . . ?
O12 C45 O11 123.0(4) . . ?
O12 C45 C44 122.4(4) . . ?
C18 C14 C11 121.9(4) . . ?
C15 C14 C11 121.0(4) . . ?
C15 C14 C18 117.0(5) . . ?
O4 C35 C34 115.1(4) . . ?
O3 C35 O4 125.3(4) . . ?
O3 C35 C34 119.3(4) . . ?
O13 C43 C42 123.6(5) . . ?
O13 C43 O14 122.1(5) . . ?
O14 C43 C42 114.2(4) . . ?
N2 C13 H13 119.5 . . ?
N2 C13 C12 120.9(4) . . ?
C12 C13 H13 119.5 . . ?
C43 O14 H14 114(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C14 C18 H18 119.7 . . ?
C17 C18 C14 120.6(4) . . ?
C17 C18 H18 119.7 . . ?
O7 C30 C29 115.2(4) . . ?
O8 C30 O7 124.0(4) . . ?
O8 C30 C29 120.7(4) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C2 120.0(5) . . ?
C2 C7 H7 120.0 . . ?
N2 C9 C10 121.1(4) . . ?
N2 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C7 C6 C8 120.2(4) . . ?
C5 C6 C7 119.0(5) . . ?
C5 C6 C8 120.7(5) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(5) . . ?
C16 C15 H15 120.0 . . ?
N2 C8 C6 112.1(4) . . ?
N2 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C6 C8 H8A 109.2 . . ?
C6 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N3 C17 C18 121.4(5) . . ?
N3 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C27 O1 H1 109.5 . . ?
N3 C16 C15 121.0(5) . . ?
N3 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C7 C2 C1 120.7(5) . . ?
C3 C2 C7 120.1(6) . . ?
C3 C2 C1 119.0(6) . . ?
C26 C20 C19 116.6(6) . . ?
C21 C20 C19 122.3(6) . . ?
C21 C20 C26 121.1(6) . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
C20 C19 N3 110.9(4) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.0 . . ?
N1 C1 C2 175.8(8) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(6) . . ?
C4 C3 H3 119.8 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C4 C5 H5 119.6 . . ?
C20 C26 H26 119.5 . . ?
C24 C26 C20 121.0(8) . . ?
C24 C26 H26 119.5 . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.8(8) . . ?
C22 C21 H21 120.6 . . ?
C24 C23 H23 118.6 . . ?
C22 C23 H23 118.6 . . ?
C22 C23 C24 122.9(8) . . ?
C26 C24 C23 117.8(8) . . ?
C26 C24 C25 120.8(9) . . ?
C23 C24 C25 121.2(8) . . ?
C3 C4 C5 119.7(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C21 C22 H22 120.8 . . ?
C23 C22 C21 118.3(9) . . ?
C23 C22 H22 120.8 . . ?
N4 C25 C24 169.6(11) . . ?

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
_geom_hbond_publ_flag
C13 H13 O5 0.93 2.34 3.175(5) 148.6 2_766 yes
C13 H13 O1 0.93 2.63 3.201(6) 120.1 1_655 yes
C12 H12 O1 0.93 2.55 3.161(6) 123.5 1_655 yes
C12 H12 O1A 0.93 2.24 3.143(9) 163.3 1_655 yes
C10 H10 O13 0.93 2.16 3.088(6) 173.1 1_546 yes
C18 H18 O8 0.93 2.23 3.120(5) 159.6 1_655 yes
C7 H7 O5 0.93 2.57 3.402(6) 149.3 2_766 yes
C7 H7 O3 0.93 2.58 3.313(6) 135.9 2_766 yes
C9 H9 O9 0.93 2.31 3.220(6) 165.2 2_666 yes
C15 H15 O12 0.93 2.42 3.332(6) 165.5 1_546 yes
C15 H15 O13 0.93 2.75 3.380(7) 126.0 1_546 yes
C8 H8A O5 0.97 2.59 3.389(5) 139.3 2_766 yes
C17 H17 O3 0.93 2.42 3.043(7) 124.1 . yes
O1 H1 O4 0.82 1.62 2.373(6) 151.7 2_666 yes
C16 H16 N4 0.93 2.35 3.219(10) 156.0 2_656 yes
C5 H5 O9 0.93 2.59 3.351(6) 139.6 2_666 yes
O16 H16A O9 1.04(5) 1.34(5) 2.364(5) 168(4) . yes
O6 H6 O10 0.88(6) 1.76(6) 2.627(4) 170(6) . yes
O11 H11 O15 1.00(7) 1.72(7) 2.704(4) 168(6) 1_655 yes
O11 H11 O16 1.00(7) 2.52(7) 3.152(5) 121(5) 1_655 yes
O14 H14 O2 0.86(2) 1.79(2) 2.649(6) 177(7) 1_564 yes
O14 H14 O1 0.86(2) 2.54(6) 3.093(7) 123(5) 1_564 yes
O14 H14 O2A 0.86(2) 2.03(4) 2.797(10) 148(6) 1_564 yes
O14 H14 O1A 0.86(2) 2.36(5) 3.009(9) 133(6) 1_564 yes
O7 H7A O4 0.84(2) 1.91(5) 2.678(4) 152(9) 1_455 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C13 C12 C11 -0.2(7) . . . . ?
C39 C38 C46 C44 -2.9(6) . . . . ?
C39 C38 C37 O10 -169.8(4) . . . . ?
C39 C38 C37 O9 15.1(6) . . . . ?
C44 C42 C41 C39 -2.1(6) . . . . ?
C44 C42 C43 O13 -40.3(8) . . . . ?
C44 C42 C43 O14 141.2(5) . . . . ?
C38 C39 C41 C42 0.0(6) . . . . ?
C38 C39 C40 O15 169.0(4) . . . . ?
C38 C39 C40 O16 -14.6(6) . . . . ?
C46 C44 C42 C41 1.6(6) . . . . ?
C46 C44 C42 C43 -179.4(4) . . . . ?
C46 C44 C45 O11 -59.0(6) . . . . ?
C46 C44 C45 O12 124.2(5) . . . . ?
C46 C38 C37 O10 11.5(6) . . . . ?
C46 C38 C37 O9 -163.5(4) . . . . ?
C42 C44 C46 C38 0.9(6) . . . . ?
C42 C44 C45 O11 126.3(5) . . . . ?
C42 C44 C45 O12 -50.5(6) . . . . ?
C41 C39 C38 C46 2.4(5) . . . . ?
C41 C39 C38 C37 -176.1(4) . . . . ?
C41 C39 C40 O15 -11.9(6) . . . . ?
C41 C39 C40 O16 164.4(4) . . . . ?
C41 C42 C43 O13 138.7(6) . . . . ?
C41 C42 C43 O14 -39.8(7) . . . . ?
C32 C31 C29 C28 0.8(6) . . . . ?
C32 C31 C29 C30 -176.2(4) . . . . ?
C32 C34 C36 C28 0.5(7) . . . . ?
C32 C34 C35 O4 94.2(5) . . . . ?
C32 C34 C35 O3 -92.0(5) . . . . ?
C31 C32 C33 O5 179.3(4) . . . . ?
C31 C32 C33 O6 -4.4(6) . . . . ?
C31 C32 C34 C36 1.0(6) . . . . ?
C31 C32 C34 C35 176.1(4) . . . . ?
C31 C29 C28 C27 -177.8(4) . . . . ?
C31 C29 C28 C36 0.7(6) . . . . ?
C31 C29 C30 O7 -23.1(7) . . . . ?
C31 C29 C30 O8 155.3(5) . . . . ?
C29 C28 C27 O2 126.4(6) . . . . ?
C29 C28 C27 O1 -63.8(6) . . . . ?
C29 C28 C27 O2A -166.6(9) . . . . ?
C29 C28 C27 O1A 28.0(8) . . . . ?
C29 C28 C36 C34 -1.3(7) . . . . ?
C33 C32 C31 C29 178.2(4) . . . . ?
C33 C32 C34 C36 -178.9(4) . . . . ?
C33 C32 C34 C35 -3.8(6) . . . . ?
C34 C32 C31 C29 -1.7(6) . . . . ?
C34 C32 C33 O5 -0.7(6) . . . . ?
C34 C32 C33 O6 175.5(4) . . . . ?
C28 C29 C30 O7 160.0(5) . . . . ?
C28 C29 C30 O8 -21.7(8) . . . . ?
C11 C14 C18 C17 178.6(4) . . . . ?
C11 C14 C15 C16 -178.5(4) . . . . ?
C11 C10 C9 N2 -0.6(7) . . . . ?
C37 C38 C46 C44 175.8(4) . . . . ?
C27 C28 C36 C34 177.3(4) . . . . ?
C36 C34 C35 O4 -90.6(5) . . . . ?
C36 C34 C35 O3 83.2(5) . . . . ?
C36 C28 C27 O2 -52.1(7) . . . . ?
C36 C28 C27 O1 117.7(5) . . . . ?
C36 C28 C27 O2A 14.9(10) . . . . ?
C36 C28 C27 O1A -150.5(6) . . . . ?
C40 C39 C38 C46 -178.5(4) . . . . ?
C40 C39 C38 C37 2.9(6) . . . . ?
C40 C39 C41 C42 -179.2(4) . . . . ?
C45 C44 C46 C38 -173.9(4) . . . . ?
C45 C44 C42 C41 176.4(4) . . . . ?
C45 C44 C42 C43 -4.6(6) . . . . ?
C14 C11 C12 C13 -179.1(4) . . . . ?
C14 C11 C10 C9 179.5(4) . . . . ?
C14 C18 C17 N3 0.3(7) . . . . ?
C14 C15 C16 N3 -0.4(8) . . . . ?
C35 C34 C36 C28 -175.0(4) . . . . ?
C43 C42 C41 C39 178.9(4) . . . . ?
C13 N2 C9 C10 0.9(7) . . . . ?
C13 N2 C8 C6 112.5(5) . . . . ?
C12 C11 C14 C18 -37.9(6) . . . . ?
C12 C11 C14 C15 141.4(4) . . . . ?
C12 C11 C10 C9 -0.2(6) . . . . ?
C10 C11 C14 C18 142.5(4) . . . . ?
C10 C11 C14 C15 -38.3(6) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
C18 C14 C15 C16 0.8(7) . . . . ?
C30 C29 C28 C27 -0.9(7) . . . . ?
C30 C29 C28 C36 177.6(4) . . . . ?
C7 C6 C8 N2 -84.4(5) . . . . ?
C7 C6 C5 C4 3.0(10) . . . . ?
C7 C2 C3 C4 -0.1(10) . . . . ?
C9 N2 C13 C12 -0.5(7) . . . . ?
C9 N2 C8 C6 -67.1(5) . . . . ?
C6 C7 C2 C1 177.1(5) . . . . ?
C6 C7 C2 C3 1.9(8) . . . . ?
C6 C5 C4 C3 -1.2(13) . . . . ?
C15 C14 C18 C17 -0.7(6) . . . . ?
C8 N2 C13 C12 179.9(4) . . . . ?
C8 N2 C9 C10 -179.5(4) . . . . ?
C8 C6 C5 C4 179.3(7) . . . . ?
C17 N3 C16 C15 0.0(8) . . . . ?
C17 N3 C19 C20 -97.4(6) . . . . ?
C16 N3 C17 C18 0.1(7) . . . . ?
C16 N3 C19 C20 80.3(7) . . . . ?
C2 C7 C6 C8 -179.6(5) . . . . ?
C2 C7 C6 C5 -3.3(8) . . . . ?
C2 C3 C4 C5 -0.3(13) . . . . ?
C20 C26 C24 C23 1.5(10) . . . . ?
C20 C26 C24 C25 -174.2(6) . . . . ?
C20 C21 C22 C23 3.8(10) . . . . ?
C19 N3 C17 C18 177.8(5) . . . . ?
C19 N3 C16 C15 -177.8(5) . . . . ?
C19 C20 C26 C24 178.7(5) . . . . ?
C19 C20 C21 C22 178.7(5) . . . . ?
C1 C2 C3 C4 -175.3(7) . . . . ?
C5 C6 C8 N2 99.4(6) . . . . ?
C26 C20 C19 N3 -82.9(6) . . . . ?
C26 C20 C21 C22 -2.1(9) . . . . ?
C26 C24 C25 N4 31(5) . . . . ?
C21 C20 C19 N3 96.3(6) . . . . ?
C21 C20 C26 C24 -0.5(9) . . . . ?
C23 C24 C25 N4 -145(5) . . . . ?
C24 C23 C22 C21 -2.9(12) . . . . ?
C22 C23 C24 C26 0.2(11) . . . . ?
C22 C23 C24 C25 176.0(7) . . . . ?

_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_201202zww3_0m
_database_code_depnum_ccdc_archive 'CCDC 2049241'
loop_
_audit_author_name
_audit_author_address
'shuxin cui'
;mdjnenu
China
;
_audit_update_record             
;
2021-11-28 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N2 O3, 2(C10 H5 O8), 2(H2 O)'
_chemical_formula_sum            'C46 H35 N2 O21'
_chemical_formula_weight         951.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_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                   9.6809(14)
_cell_length_b                   15.526(2)
_cell_length_c                   13.6809(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.407(3)
_cell_angle_gamma                90
_cell_volume                     2050.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1466
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.513
_cell_measurement_theta_min      2.485
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0644 before and 0.0344 after correction.
The Ratio of minimum to maximum transmission is 0.9366.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             986
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.1448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12125
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.691
_diffrn_reflns_theta_min         1.987
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1940
_reflns_number_total             4797
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2066
_refine_ls_R_factor_gt           0.0896
_refine_ls_restrained_S_all      1.062
_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)+(0.0782P)²+0.0450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.2192
_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, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C13A) = Uanis(C13B)
3. Others
 Sof(C13B)=1-FVAR(1)
 Sof(C13A)=FVAR(1)
 Fixed Sof: O2(0.5) H2A(0.5)
4.a Free rotating group:
 OW1(HW1A,HW1B)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C18(H18), C2(H2), C3(H3), C5(H5), C4(H4), C8(H8), C12(H12), C9(H9),
 C11(H11)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.7842(3) 0.7810(2) 0.3444(2) 0.0460(8) Uani 1 1 d . . . . .
O10 O 0.0478(3) 0.7630(2) 0.3763(3) 0.0585(11) Uani 1 1 d . . . . .
O5 O 0.7720(3) 0.7522(2) 0.5022(2) 0.0561(10) Uani 1 1 d . . . . .
O4 O 0.6404(3) 0.60312(19) 0.3953(3) 0.0634(10) Uani 1 1 d . . . . .
O3 O 0.4226(3) 0.5638(2) 0.3888(3) 0.0644(11) Uani 1 1 d . . . . .
OW1 O 0.2600(4) 1.1769(2) 0.3220(2) 0.0669(11) Uani 1 1 d G . . . .
HW1A H 0.266075 1.204625 0.375716 0.100 Uiso 1 1 d G U . . .
HW1B H 0.265630 1.215258 0.278184 0.100 Uiso 1 1 d G U . . .
O8 O 0.3535(4) 1.0171(2) 0.3185(3) 0.0710(12) Uani 1 1 d . . . . .
N1 N 0.9171(4) 0.0244(2) 0.2429(3) 0.0472(10) Uani 1 1 d . . . . .
C16 C 0.5622(4) 0.7810(3) 0.4052(3) 0.0293(10) Uani 1 1 d . . . . .
C15 C 0.4698(4) 0.7124(2) 0.3964(3) 0.0287(9) Uani 1 1 d . . . . .
C21 C 0.2771(4) 0.8123(2) 0.3812(3) 0.0264(9) Uani 1 1 d . . . . .
C19 C 0.3687(4) 0.8808(2) 0.3899(3) 0.0280(9) Uani 1 1 d . . . . .
C23 C 0.3278(4) 0.7295(3) 0.3850(3) 0.0314(10) Uani 1 1 d . . . . .
H23 H 0.265842 0.683659 0.379839 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7195(4) 0.7694(3) 0.4196(3) 0.0345(10) Uani 1 1 d . . . . .
C18 C 0.5106(4) 0.8639(3) 0.4025(3) 0.0344(10) Uani 1 1 d . . . . .
H18 H 0.572138 0.909909 0.409235 0.041 Uiso 1 1 calc R U . . .
C22 C 0.1249(4) 0.8277(3) 0.3622(3) 0.0389(11) Uani 1 1 d . . . . .
O7 O 0.2677(5) 1.0029(2) 0.4596(3) 0.0937(15) Uani 1 1 d . . . . .
C14 C 0.5174(5) 0.6213(3) 0.3936(3) 0.0392(11) Uani 1 1 d . . . . .
C20 C 0.3216(5) 0.9726(3) 0.3928(4) 0.0406(11) Uani 1 1 d . . . . .
C1 C 0.9812(4) 0.0048(3) 0.0515(3) 0.0374(11) Uani 1 1 d . . . . .
O9 O 0.0801(4) 0.8942(2) 0.3322(4) 0.1156(19) Uani 1 1 d . . . . .
O1 O 0.5069(5) 0.3976(3) 0.3693(3) 0.1014(15) Uani 1 1 d . . . . .
C2 C 0.8867(5) -0.0480(3) 0.0927(4) 0.0537(13) Uani 1 1 d . . . . .
H2 H 0.842940 -0.091678 0.055520 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8129(5) 0.1225(3) 0.3606(3) 0.0498(13) Uani 1 1 d . . . . .
C3 C 0.8568(5) -0.0364(3) 0.1885(4) 0.0578(14) Uani 1 1 d . . . . .
H3 H 0.792633 -0.072342 0.215151 0.069 Uiso 1 1 calc R U . . .
C5 C 1.0421(5) 0.0672(3) 0.1106(4) 0.0603(15) Uani 1 1 d . . . . .
H5 H 1.106951 0.104150 0.086407 0.072 Uiso 1 1 calc R U . . .
C4 C 1.0081(6) 0.0754(3) 0.2052(4) 0.0630(15) Uani 1 1 d . . . . .
H4 H 1.050481 0.118300 0.244309 0.076 Uiso 1 1 calc R U . . .
C8 C 0.6742(6) 0.1257(4) 0.3463(4) 0.0605(15) Uani 1 1 d . . . . .
H8 H 0.624597 0.075317 0.332045 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8870(6) 0.1970(4) 0.3820(4) 0.0650(15) Uani 1 1 d . . . . .
H12 H 0.982911 0.195253 0.393217 0.078 Uiso 1 1 calc R U . . .
C6 C 0.8865(6) 0.0367(3) 0.3496(4) 0.0717(16) Uani 1 1 d . . . . .
H6A H 0.972363 0.035937 0.391119 0.086 Uiso 1 1 calc R U . . .
H6B H 0.828457 -0.009955 0.369794 0.086 Uiso 1 1 calc R U . . .
C9 C 0.6046(6) 0.2025(5) 0.3525(4) 0.0785(18) Uani 1 1 d . . . . .
H9 H 0.508389 0.203642 0.344426 0.094 Uiso 1 1 calc R U . . .
C10 C 0.6767(9) 0.2769(5) 0.3706(4) 0.081(2) Uani 1 1 d . . . . .
C11 C 0.8165(8) 0.2743(4) 0.3865(4) 0.0781(18) Uani 1 1 d . . . . .
H11 H 0.865591 0.324909 0.400517 0.094 Uiso 1 1 calc R U . . .
O2 O 0.7236(9) 0.4373(5) 0.3960(7) 0.093(3) Uani 0.5 1 d . . P . .
H2A H 0.679652 0.482475 0.390959 0.139 Uiso 0.5 1 calc R U P A 1
C13B C 0.5700(17) 0.3391(8) 0.3663(9) 0.062(3) Uani 0.503(11) 1 d . . P B 2
H8A H 0.315(5) 1.069(4) 0.335(4) 0.079(18) Uiso 1 1 d . . . . .
H10 H -0.037(6) 0.774(4) 0.363(4) 0.09(2) Uiso 1 1 d . . . . .
H3A H 0.449(6) 0.504(4) 0.381(4) 0.12(2) Uiso 1 1 d . . . . .
C13A C 0.6421(19) 0.3747(8) 0.3816(9) 0.062(3) Uani 0.497(11) 1 d . . P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 C17 1.258(5) . ?
O10 C22 1.275(5) . ?
O10 H10 0.84(6) . ?
O5 C17 1.232(5) . ?
O4 C14 1.222(5) . ?
O3 C14 1.278(5) . ?
O3 H3A 0.98(7) . ?
OW1 HW1A 0.8500 . ?
OW1 HW1B 0.8495 . ?
O8 C20 1.286(5) . ?
O8 H8A 0.92(5) . ?
N1 C3 1.311(6) . ?
N1 C4 1.318(6) . ?
N1 C6 1.524(6) . ?
C16 C15 1.390(5) . ?
C16 C17 1.531(5) . ?
C16 C18 1.380(5) . ?
C15 C23 1.397(5) . ?
C15 C14 1.490(5) . ?
C21 C19 1.383(5) . ?
C21 C23 1.376(5) . ?
C21 C22 1.495(5) . ?
C19 C18 1.396(5) . ?
C19 C20 1.498(6) . ?
C23 H23 0.9300 . ?
C18 H18 0.9300 . ?
C22 O9 1.180(5) . ?
O7 C20 1.185(5) . ?
C1 C1 1.489(8) 3_755 ?
C1 C2 1.382(6) . ?
C1 C5 1.366(6) . ?
O1 C13B 1.096(13) . ?
O1 C13A 1.354(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(6) . ?
C7 C8 1.343(7) . ?
C7 C12 1.380(7) . ?
C7 C6 1.524(6) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.365(6) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.376(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.385(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.363(8) . ?
C10 C11 1.355(9) . ?
C10 C13B 1.412(15) . ?
C10 C13A 1.564(13) . ?
C11 H11 0.9300 . ?
O2 H2A 0.8200 . ?
O2 C13A 1.258(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O10 H10 112(4) . . ?
C14 O3 H3A 119(4) . . ?
HW1A OW1 HW1B 104.6 . . ?
C20 O8 H8A 99(3) . . ?
C3 N1 C4 119.5(4) . . ?
C3 N1 C6 121.5(4) . . ?
C4 N1 C6 118.9(5) . . ?
C15 C16 C17 123.2(3) . . ?
C18 C16 C15 118.9(3) . . ?
C18 C16 C17 117.9(3) . . ?
C16 C15 C23 119.0(4) . . ?
C16 C15 C14 122.1(4) . . ?
C23 C15 C14 118.8(4) . . ?
C19 C21 C22 120.6(3) . . ?
C23 C21 C19 119.3(3) . . ?
C23 C21 C22 120.0(3) . . ?
C21 C19 C18 119.0(4) . . ?
C21 C19 C20 122.6(4) . . ?
C18 C19 C20 118.3(4) . . ?
C15 C23 H23 119.1 . . ?
C21 C23 C15 121.8(4) . . ?
C21 C23 H23 119.1 . . ?
O6 C17 C16 115.5(4) . . ?
O5 C17 O6 125.8(4) . . ?
O5 C17 C16 118.7(4) . . ?
C16 C18 C19 121.9(4) . . ?
C16 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
O10 C22 C21 115.4(4) . . ?
O9 C22 O10 122.5(4) . . ?
O9 C22 C21 122.1(4) . . ?
O4 C14 O3 122.4(4) . . ?
O4 C14 C15 121.5(4) . . ?
O3 C14 C15 116.2(4) . . ?
O8 C20 C19 113.5(4) . . ?
O7 C20 O8 122.9(5) . . ?
O7 C20 C19 123.5(4) . . ?
C2 C1 C1 123.0(5) . 3_755 ?
C5 C1 C1 120.4(5) . 3_755 ?
C5 C1 C2 116.6(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C8 C7 C12 119.9(5) . . ?
C8 C7 C6 119.2(5) . . ?
C12 C7 C6 120.9(5) . . ?
N1 C3 C2 121.2(5) . . ?
N1 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C1 C5 H5 119.9 . . ?
C4 C5 C1 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
N1 C4 C5 122.1(5) . . ?
N1 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.7(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C12 H12 120.5 . . ?
C7 C12 C11 119.1(5) . . ?
C11 C12 H12 120.5 . . ?
N1 C6 C7 109.4(4) . . ?
N1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(6) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C13B 102.1(9) . . ?
C9 C10 C13A 136.9(10) . . ?
C11 C10 C9 119.7(6) . . ?
C11 C10 C13B 138.2(10) . . ?
C11 C10 C13A 103.4(10) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.5(6) . . ?
C10 C11 H11 119.7 . . ?
C13A O2 H2A 109.5 . . ?
O1 C13B C10 166.5(15) . . ?
O1 C13A C10 117.0(13) . . ?
O2 C13A O1 113.9(10) . . ?
O2 C13A C10 129.0(14) . . ?

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
_geom_hbond_publ_flag
OW1 HW1A O5 0.85 1.86 2.685(5) 162.3 3_676 yes
OW1 HW1B O6 0.85 1.99 2.798(4) 158.3 2_655 yes
O2 H2A O4 0.82 1.91 2.697(8) 159.6 . yes
O8 H8A OW1 0.92(5) 1.77(6) 2.644(5) 158(5) . yes
O10 H10 O6 0.84(6) 1.74(6) 2.572(4) 171(6) 1_455 yes
O3 H3A O1 0.98(7) 1.75(7) 2.727(5) 176(6) . yes

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
C16 C15 C23 C21 0.7(6) . . . . ?
C16 C15 C14 O4 -2.7(6) . . . . ?
C16 C15 C14 O3 177.6(4) . . . . ?
C15 C16 C17 O6 102.3(4) . . . . ?
C15 C16 C17 O5 -79.6(5) . . . . ?
C15 C16 C18 C19 -0.8(6) . . . . ?
C21 C19 C18 C16 0.8(6) . . . . ?
C21 C19 C20 O8 -114.5(4) . . . . ?
C21 C19 C20 O7 69.8(6) . . . . ?
C19 C21 C23 C15 -0.7(6) . . . . ?
C19 C21 C22 O10 -165.5(4) . . . . ?
C19 C21 C22 O9 17.7(7) . . . . ?
C23 C15 C14 O4 174.1(4) . . . . ?
C23 C15 C14 O3 -5.6(6) . . . . ?
C23 C21 C19 C18 0.0(5) . . . . ?
C23 C21 C19 C20 -176.1(4) . . . . ?
C23 C21 C22 O10 17.9(6) . . . . ?
C23 C21 C22 O9 -158.9(5) . . . . ?
C17 C16 C15 C23 179.0(4) . . . . ?
C17 C16 C15 C14 -4.2(6) . . . . ?
C17 C16 C18 C19 -179.8(4) . . . . ?
C18 C16 C15 C23 0.1(5) . . . . ?
C18 C16 C15 C14 176.8(4) . . . . ?
C18 C16 C17 O6 -78.7(5) . . . . ?
C18 C16 C17 O5 99.3(5) . . . . ?
C18 C19 C20 O8 69.4(5) . . . . ?
C18 C19 C20 O7 -106.3(5) . . . . ?
C22 C21 C19 C18 -176.7(4) . . . . ?
C22 C21 C19 C20 7.2(6) . . . . ?
C22 C21 C23 C15 175.9(4) . . . . ?
C14 C15 C23 C21 -176.2(4) . . . . ?
C20 C19 C18 C16 177.1(4) . . . . ?
C1 C1 C2 C3 179.5(5) 3_755 . . . ?
C1 C1 C5 C4 -179.5(5) 3_755 . . . ?
C1 C2 C3 N1 -0.3(7) . . . . ?
C1 C5 C4 N1 0.2(8) . . . . ?
C2 C1 C5 C4 -0.4(7) . . . . ?
C7 C8 C9 C10 1.9(8) . . . . ?
C7 C12 C11 C10 0.3(8) . . . . ?
C3 N1 C4 C5 0.0(7) . . . . ?
C3 N1 C6 C7 -113.5(5) . . . . ?
C5 C1 C2 C3 0.5(7) . . . . ?
C4 N1 C3 C2 0.0(7) . . . . ?
C4 N1 C6 C7 67.6(6) . . . . ?
C8 C7 C12 C11 -1.2(7) . . . . ?
C8 C7 C6 N1 87.9(6) . . . . ?
C8 C9 C10 C11 -2.8(9) . . . . ?
C8 C9 C10 C13B 177.2(7) . . . . ?
C8 C9 C10 C13A 178.9(8) . . . . ?
C12 C7 C8 C9 0.1(8) . . . . ?
C12 C7 C6 N1 -90.1(6) . . . . ?
C6 N1 C3 C2 -178.9(4) . . . . ?
C6 N1 C4 C5 179.0(5) . . . . ?
C6 C7 C8 C9 -177.9(5) . . . . ?
C6 C7 C12 C11 176.8(4) . . . . ?
C9 C10 C11 C12 1.7(9) . . . . ?
C9 C10 C13B O1 172(5) . . . . ?
C9 C10 C13A O1 -1.6(16) . . . . ?
C9 C10 C13A O2 -177.8(9) . . . . ?
C11 C10 C13B O1 -8(6) . . . . ?
C11 C10 C13A O1 179.9(8) . . . . ?
C11 C10 C13A O2 3.8(14) . . . . ?
C13B C10 C11 C12 -178.3(9) . . . . ?
C13A C10 C11 C12 -179.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
