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

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

data_r20230530b_autored
_database_code_depnum_ccdc_archive 'CCDC 2283871'
loop_
_audit_author_name
_audit_author_address
'Zhang liang'
;Tianjin University
China
;
_audit_update_record             
;
2023-07-24 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7 H4 Cl O3, C14 H19 N4 O3'
_chemical_formula_sum            'C21 H23 Cl N4 O6'
_chemical_formula_weight         462.88
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   11.7204(2)
_cell_length_b                   8.4362(2)
_cell_length_c                   21.7076(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.393(2)
_cell_angle_gamma                90
_cell_volume                     2123.37(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15316
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.6300
_cell_measurement_theta_min      1.8630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            29871
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_min         1.870
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    1.00    --  -20.00   0.00   0.00  360
  2  ω   -110.00  70.00   0.50    1.00    --  -20.00   0.00 180.00  360
  3  ω   -110.00   6.00   0.50    1.00    --  -20.00 -70.00 180.00  232
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 944'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0379790000
_diffrn_orient_matrix_UB_12      -0.0407053000
_diffrn_orient_matrix_UB_13      -0.0171388000
_diffrn_orient_matrix_UB_21      0.0045650000
_diffrn_orient_matrix_UB_22      -0.0627595000
_diffrn_orient_matrix_UB_23      0.0219553000
_diffrn_orient_matrix_UB_31      -0.0477659000
_diffrn_orient_matrix_UB_32      -0.0383832000
_diffrn_orient_matrix_UB_33      -0.0177389000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5012
_reflns_number_total             5924
_reflns_odcompleteness_completeness 91.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     34.66
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.322
_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     316
_refine_ls_number_reflns         5924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.036
_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)+(0.0556P)²+0.9494P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1178
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
1.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C20(H20), C4(H4A), C7(H7), C11(H11)
1.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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
Cl1 Cl 0.15373(3) 0.03227(5) 0.28967(2) 0.03098(11) Uani 1 1 d . . . . .
O4 O -0.20000(10) 0.52081(14) 0.22523(6) 0.0304(3) Uani 1 1 d . . . . .
H4B H -0.178(2) 0.601(3) 0.2565(12) 0.059(7) Uiso 1 1 d . . . . .
O5 O -0.10582(9) 0.67901(13) 0.31731(5) 0.0262(2) Uani 1 1 d . . . . .
O6 O 0.04072(9) 0.58183(12) 0.38356(5) 0.0216(2) Uani 1 1 d . . . . .
C15 C -0.11799(12) 0.41006(17) 0.24194(7) 0.0207(3) Uani 1 1 d . . . . .
C16 C -0.03168(11) 0.43008(16) 0.29355(6) 0.0171(3) Uani 1 1 d . . . . .
C17 C 0.05289(11) 0.31416(16) 0.30690(6) 0.0185(3) Uani 1 1 d . . . . .
H17 H 0.1131 0.3281 0.3408 0.022 Uiso 1 1 calc R U . . .
C18 C 0.04913(12) 0.17902(17) 0.27078(7) 0.0208(3) Uani 1 1 d . . . . .
C19 C -0.03824(12) 0.15490(18) 0.22102(7) 0.0225(3) Uani 1 1 d . . . . .
H19 H -0.0413 0.0598 0.1974 0.027 Uiso 1 1 calc R U . . .
C20 C -0.12052(12) 0.27129(18) 0.20642(7) 0.0229(3) Uani 1 1 d . . . . .
H20 H -0.1795 0.2571 0.1719 0.027 Uiso 1 1 calc R U . . .
C21 C -0.03140(11) 0.57305(16) 0.33489(6) 0.0182(3) Uani 1 1 d . . . . .
O1 O 0.50885(9) 1.29696(13) 0.34994(5) 0.0245(2) Uani 1 1 d . . . . .
O2 O 0.66807(9) 1.45079(12) 0.43173(5) 0.0260(2) Uani 1 1 d . . . . .
O3 O 0.67541(8) 1.41384(12) 0.55325(5) 0.0221(2) Uani 1 1 d . . . . .
N1 N -0.10005(10) 0.97404(16) 0.37535(6) 0.0214(2) Uani 1 1 d . . . . .
H1A H -0.1058(17) 0.884(3) 0.3549(10) 0.036(5) Uiso 1 1 d . . . . .
H1B H -0.1410(17) 1.052(2) 0.3582(9) 0.031(5) Uiso 1 1 d . . . . .
N2 N 0.15189(11) 1.33656(15) 0.47641(6) 0.0215(3) Uani 1 1 d . . . . .
H2A H 0.1033(17) 1.409(2) 0.4565(9) 0.033(5) Uiso 1 1 d . . . . .
H2B H 0.2208(18) 1.366(2) 0.4955(9) 0.037(5) Uiso 1 1 d . . . . .
N3 N 0.02430(9) 1.15514(13) 0.42934(5) 0.0167(2) Uani 1 1 d . . . . .
N4 N 0.07211(9) 0.88422(14) 0.42826(5) 0.0169(2) Uani 1 1 d . . . . .
H4 H 0.0558(16) 0.784(2) 0.4155(9) 0.028(5) Uiso 1 1 d . . . . .
C1 C -0.00058(11) 1.00686(16) 0.41124(6) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.12788(11) 1.18465(16) 0.46316(6) 0.0159(2) Uani 1 1 d . . . . .
C3 C 0.20874(11) 1.06064(16) 0.48354(6) 0.0154(2) Uani 1 1 d . . . . .
C4 C 0.17521(11) 0.91282(16) 0.46450(6) 0.0167(2) Uani 1 1 d . . . . .
H4A H 0.2251 0.8262 0.4768 0.020 Uiso 1 1 calc R U . . .
C5 C 0.32082(11) 1.08962(17) 0.52538(6) 0.0178(3) Uani 1 1 d . . . . .
H5A H 0.3538 0.9855 0.5394 0.021 Uiso 1 1 calc R U . . .
H5B H 0.3035 1.1467 0.5628 0.021 Uiso 1 1 calc R U . . .
C6 C 0.41290(10) 1.18258(15) 0.49819(6) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.41451(11) 1.19106(16) 0.43425(6) 0.0176(3) Uani 1 1 d . . . . .
H7 H 0.3571 1.1384 0.4061 0.021 Uiso 1 1 calc R U . . .
C8 C 0.50142(11) 1.27782(16) 0.41181(6) 0.0183(3) Uani 1 1 d . . . . .
C9 C 0.58656(11) 1.35407(16) 0.45257(7) 0.0183(3) Uani 1 1 d . . . . .
C10 C 0.58601(11) 1.34070(15) 0.51663(7) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.49865(11) 1.25650(15) 0.53924(6) 0.0163(2) Uani 1 1 d . . . . .
H11 H 0.4977 1.2496 0.5828 0.020 Uiso 1 1 calc R U . . .
C12 C 0.43122(15) 1.2070(2) 0.30704(7) 0.0294(3) Uani 1 1 d . . . . .
H12A H 0.4509 1.2204 0.2650 0.044 Uiso 1 1 calc R U . . .
H12B H 0.3522 1.2439 0.3079 0.044 Uiso 1 1 calc R U . . .
H12C H 0.4371 1.0947 0.3186 0.044 Uiso 1 1 calc R U . . .
C13 C 0.75096(13) 1.3721(2) 0.39961(8) 0.0301(3) Uani 1 1 d . . . . .
H13A H 0.7114 1.3248 0.3611 0.045 Uiso 1 1 calc R U . . .
H13B H 0.7898 1.2887 0.4263 0.045 Uiso 1 1 calc R U . . .
H13C H 0.8081 1.4491 0.3896 0.045 Uiso 1 1 calc R U . . .
C14 C 0.68128(13) 1.3957(2) 0.61888(7) 0.0266(3) Uani 1 1 d . . . . .
H14A H 0.6849 1.2827 0.6295 0.040 Uiso 1 1 calc R U . . .
H14B H 0.6126 1.4427 0.6324 0.040 Uiso 1 1 calc R U . . .
H14C H 0.7504 1.4492 0.6399 0.040 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
Cl1 C18 1.7484(15) . ?
O4 H4B 0.97(3) . ?
O4 C15 1.3515(18) . ?
O5 C21 1.2682(17) . ?
O6 C21 1.2553(17) . ?
C15 C16 1.4057(19) . ?
C15 C20 1.400(2) . ?
C16 C17 1.3925(19) . ?
C16 C21 1.5031(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3806(19) . ?
C18 C19 1.391(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(2) . ?
C20 H20 0.9500 . ?
O1 C8 1.3680(16) . ?
O1 C12 1.422(2) . ?
O2 C9 1.3816(16) . ?
O2 C13 1.4381(18) . ?
O3 C10 1.3665(16) . ?
O3 C14 1.4244(19) . ?
N1 H1A 0.88(2) . ?
N1 H1B 0.87(2) . ?
N1 C1 1.3333(17) . ?
N2 H2A 0.90(2) . ?
N2 H2B 0.89(2) . ?
N2 C2 1.3344(17) . ?
N3 C1 1.3307(17) . ?
N3 C2 1.3471(17) . ?
N4 H4 0.90(2) . ?
N4 C1 1.3568(17) . ?
N4 C4 1.3638(17) . ?
C2 C3 1.4373(18) . ?
C3 C4 1.3538(18) . ?
C3 C5 1.5040(18) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5212(17) . ?
C6 C7 1.3927(18) . ?
C6 C11 1.3898(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3983(18) . ?
C8 C9 1.391(2) . ?
C9 C10 1.396(2) . ?
C10 C11 1.3929(18) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O4 H4B 101.0(14) . . ?
O4 C15 C16 122.13(13) . . ?
O4 C15 C20 118.25(13) . . ?
C20 C15 C16 119.62(13) . . ?
C15 C16 C21 120.71(12) . . ?
C17 C16 C15 119.28(12) . . ?
C17 C16 C21 119.99(12) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.93(13) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 Cl1 119.23(11) . . ?
C17 C18 C19 121.38(13) . . ?
C19 C18 Cl1 119.35(11) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.00(13) . . ?
C20 C19 H19 120.5 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.71(13) . . ?
C19 C20 H20 119.6 . . ?
O5 C21 C16 116.39(12) . . ?
O6 C21 O5 124.11(13) . . ?
O6 C21 C16 119.50(12) . . ?
C8 O1 C12 116.96(11) . . ?
C9 O2 C13 115.75(11) . . ?
C10 O3 C14 117.02(11) . . ?
H1A N1 H1B 116.4(19) . . ?
C1 N1 H1A 118.1(13) . . ?
C1 N1 H1B 118.4(13) . . ?
H2A N2 H2B 120.1(19) . . ?
C2 N2 H2A 116.5(13) . . ?
C2 N2 H2B 121.5(14) . . ?
C1 N3 C2 118.41(11) . . ?
C1 N4 H4 122.3(12) . . ?
C1 N4 C4 119.37(12) . . ?
C4 N4 H4 118.3(12) . . ?
N1 C1 N4 117.48(12) . . ?
N3 C1 N1 120.20(12) . . ?
N3 C1 N4 122.32(12) . . ?
N2 C2 N3 116.09(12) . . ?
N2 C2 C3 121.59(12) . . ?
N3 C2 C3 122.31(12) . . ?
C2 C3 C5 123.10(12) . . ?
C4 C3 C2 115.31(12) . . ?
C4 C3 C5 121.54(12) . . ?
N4 C4 H4A 118.9 . . ?
C3 C4 N4 122.16(12) . . ?
C3 C4 H4A 118.9 . . ?
C3 C5 H5A 108.0 . . ?
C3 C5 H5B 108.0 . . ?
C3 C5 C6 117.13(11) . . ?
H5A C5 H5B 107.3 . . ?
C6 C5 H5A 108.0 . . ?
C6 C5 H5B 108.0 . . ?
C7 C6 C5 121.79(12) . . ?
C11 C6 C5 118.04(12) . . ?
C11 C6 C7 120.14(12) . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.38(13) . . ?
C8 C7 H7 120.3 . . ?
O1 C8 C7 123.90(13) . . ?
O1 C8 C9 115.30(12) . . ?
C9 C8 C7 120.79(13) . . ?
O2 C9 C8 122.08(13) . . ?
O2 C9 C10 118.53(12) . . ?
C8 C9 C10 119.27(12) . . ?
O3 C10 C9 115.36(11) . . ?
O3 C10 C11 124.47(13) . . ?
C11 C10 C9 120.17(12) . . ?
C6 C11 C10 120.19(12) . . ?
C6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C19 C20 179.97(11) . . . . ?
O4 C15 C16 C17 -177.59(13) . . . . ?
O4 C15 C16 C21 3.7(2) . . . . ?
O4 C15 C20 C19 179.37(13) . . . . ?
C15 C16 C17 C18 -2.1(2) . . . . ?
C15 C16 C21 O5 -6.26(19) . . . . ?
C15 C16 C21 O6 174.06(13) . . . . ?
C16 C15 C20 C19 -0.9(2) . . . . ?
C16 C17 C18 Cl1 -178.17(10) . . . . ?
C16 C17 C18 C19 -0.3(2) . . . . ?
C17 C16 C21 O5 175.00(12) . . . . ?
C17 C16 C21 O6 -4.68(19) . . . . ?
C17 C18 C19 C20 2.1(2) . . . . ?
C18 C19 C20 C15 -1.5(2) . . . . ?
C20 C15 C16 C17 2.7(2) . . . . ?
C20 C15 C16 C21 -176.06(12) . . . . ?
C21 C16 C17 C18 176.67(12) . . . . ?
O1 C8 C9 O2 4.14(19) . . . . ?
O1 C8 C9 C10 -179.81(11) . . . . ?
O2 C9 C10 O3 -6.41(17) . . . . ?
O2 C9 C10 C11 173.93(12) . . . . ?
O3 C10 C11 C6 -178.29(12) . . . . ?
N2 C2 C3 C4 -177.23(13) . . . . ?
N2 C2 C3 C5 5.4(2) . . . . ?
N3 C2 C3 C4 2.23(19) . . . . ?
N3 C2 C3 C5 -175.17(12) . . . . ?
C1 N3 C2 N2 175.44(12) . . . . ?
C1 N3 C2 C3 -4.05(19) . . . . ?
C1 N4 C4 C3 -0.99(19) . . . . ?
C2 N3 C1 N1 -176.98(12) . . . . ?
C2 N3 C1 N4 3.37(19) . . . . ?
C2 C3 C4 N4 0.33(19) . . . . ?
C2 C3 C5 C6 -68.74(17) . . . . ?
C3 C5 C6 C7 -23.05(18) . . . . ?
C3 C5 C6 C11 158.71(12) . . . . ?
C4 N4 C1 N1 179.43(12) . . . . ?
C4 N4 C1 N3 -0.90(19) . . . . ?
C4 C3 C5 C6 114.01(14) . . . . ?
C5 C3 C4 N4 177.78(12) . . . . ?
C5 C6 C7 C8 -179.80(12) . . . . ?
C5 C6 C11 C10 178.88(12) . . . . ?
C6 C7 C8 O1 -178.17(12) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C7 C6 C11 C10 0.61(19) . . . . ?
C7 C8 C9 O2 -174.78(12) . . . . ?
C7 C8 C9 C10 1.3(2) . . . . ?
C8 C9 C10 O3 177.40(12) . . . . ?
C8 C9 C10 C11 -2.26(19) . . . . ?
C9 C10 C11 C6 1.34(19) . . . . ?
C11 C6 C7 C8 -1.60(19) . . . . ?
C12 O1 C8 C7 -7.82(19) . . . . ?
C12 O1 C8 C9 173.30(13) . . . . ?
C13 O2 C9 C8 -68.49(18) . . . . ?
C13 O2 C9 C10 115.43(15) . . . . ?
C14 O3 C10 C9 -176.73(12) . . . . ?
C14 O3 C10 C11 2.91(19) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.577
_oxdiff_exptl_absorpt_empirical_full_min 0.362
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_r20230617c_autored
_database_code_depnum_ccdc_archive 'CCDC 2283924'
loop_
_audit_author_name
_audit_author_address
'zhang liang'
;Tianjin University
China
;
_audit_update_record             
;
2024-05-19 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H11 O5, C14 H19 N4 O3'
_chemical_formula_sum            'C24 H30 N4 O8'
_chemical_formula_weight         502.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.5775(9)
_cell_length_b                   8.5067(4)
_cell_length_c                   16.7661(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.408(6)
_cell_angle_gamma                90
_cell_volume                     2404.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4672
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.1890
_cell_measurement_theta_min      2.4050
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19423
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.416
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_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    -93.00  30.00   0.50    1.50    --  -30.00  15.00 180.00  246
  2  ω   -120.00  -9.00   0.50    1.50    --  -30.00 -70.00 180.00  222
  3  ω    -66.00  45.00   0.50    1.50    --  -30.00  70.00 180.00  222
  4  ω   -120.00 -10.00   0.50    1.50    --  -30.00 -70.00  90.00  220
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0264225000
_diffrn_orient_matrix_UB_12      -0.0648794000
_diffrn_orient_matrix_UB_13      -0.0080132000
_diffrn_orient_matrix_UB_21      -0.0312397000
_diffrn_orient_matrix_UB_22      0.0501375000
_diffrn_orient_matrix_UB_23      -0.0216762000
_diffrn_orient_matrix_UB_31      0.0097820000
_diffrn_orient_matrix_UB_32      -0.0151580000
_diffrn_orient_matrix_UB_33      -0.0375394000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3427
_reflns_number_total             4928
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         4928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0918
_refine_ls_restrained_S_all      1.144
_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)+(0.0689P)²+1.2682P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.2000
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4), C17(H17), C8(H8), C21(H21)
2.c Idealised Me refined as rotating group:
 C3(H3C,H3D,H3E), C24(H24A,H24B,H24C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C),
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_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
O4 O 0.42816(13) 0.5714(3) 0.74359(14) 0.0305(6) Uani 1 1 d . . . . .
O2 O 0.08935(13) 0.1152(3) 0.09509(14) 0.0324(6) Uani 1 1 d . . . . .
O1 O 0.22293(15) 0.1709(3) 0.03538(14) 0.0367(6) Uani 1 1 d . . . . .
O3 O 0.10306(14) 0.1589(3) 0.25969(15) 0.0359(6) Uani 1 1 d . . . . .
O5 O 0.35724(14) 0.6688(3) 0.61991(15) 0.0356(6) Uani 1 1 d . . . . .
O8 O 0.24347(15) 0.6620(3) 0.92955(15) 0.0401(7) Uani 1 1 d . . . . .
O6 O 0.11142(14) 0.9150(3) 0.67815(16) 0.0393(7) Uani 1 1 d . . . . .
O7 O 0.11709(14) 0.8280(3) 0.83263(16) 0.0388(7) Uani 1 1 d . . . . .
N1 N 0.41250(16) 0.4604(4) 0.53387(18) 0.0276(7) Uani 1 1 d . . . . .
N2 N 0.47225(16) 0.2137(3) 0.52228(17) 0.0272(7) Uani 1 1 d . . . . .
N3 N 0.48288(18) 0.3266(4) 0.65148(19) 0.0301(7) Uani 1 1 d . . . . .
N4 N 0.46339(19) 0.1077(4) 0.3945(2) 0.0314(7) Uani 1 1 d . . . . .
C15 C 0.3679(2) 0.6424(4) 0.6971(2) 0.0285(8) Uani 1 1 d . . . . .
C9 C 0.30274(19) 0.2930(4) 0.2532(2) 0.0269(8) Uani 1 1 d . . . . .
C14 C 0.38621(19) 0.4734(4) 0.4487(2) 0.0284(8) Uani 1 1 d . . . . .
H14 H 0.3571 0.5618 0.4256 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3034(2) 0.6990(4) 0.7351(2) 0.0278(8) Uani 1 1 d . . . . .
C13 C 0.45589(19) 0.3323(4) 0.5681(2) 0.0279(8) Uani 1 1 d . . . . .
C4 C 0.23939(19) 0.2574(4) 0.2852(2) 0.0296(8) Uani 1 1 d . . . . .
H4 H 0.2438 0.2779 0.3408 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3064(2) 0.6558(4) 0.8162(2) 0.0298(8) Uani 1 1 d . . . . .
H17 H 0.3494 0.5985 0.8480 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2957(2) 0.2572(4) 0.1701(2) 0.0297(8) Uani 1 1 d . . . . .
H8 H 0.3378 0.2784 0.1484 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1618(2) 0.1589(4) 0.1496(2) 0.0299(8) Uani 1 1 d . . . . .
C11 C 0.40126(19) 0.3615(4) 0.3972(2) 0.0260(8) Uani 1 1 d . . . . .
C12 C 0.44545(19) 0.2275(4) 0.4377(2) 0.0263(8) Uani 1 1 d . . . . .
C7 C 0.2263(2) 0.1900(4) 0.1190(2) 0.0295(8) Uani 1 1 d . . . . .
C5 C 0.1696(2) 0.1916(4) 0.2344(2) 0.0301(8) Uani 1 1 d . . . . .
C20 C 0.1780(2) 0.8313(4) 0.7207(2) 0.0321(9) Uani 1 1 d . . . . .
C21 C 0.2392(2) 0.7886(4) 0.6875(2) 0.0311(8) Uani 1 1 d . . . . .
H21 H 0.2377 0.8193 0.6338 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2447(2) 0.6988(4) 0.8500(2) 0.0331(9) Uani 1 1 d . . . . .
C10 C 0.3760(2) 0.3829(4) 0.3035(2) 0.0290(8) Uani 1 1 d . . . . .
H10A H 0.4203 0.3528 0.2830 0.035 Uiso 1 1 calc R U . . .
H10B H 0.3666 0.4940 0.2920 0.035 Uiso 1 1 calc R U . . .
C19 C 0.1796(2) 0.7848(4) 0.8017(2) 0.0331(9) Uani 1 1 d . . . . .
C3 C 0.1967(2) 0.0190(4) -0.0011(2) 0.0375(9) Uani 1 1 d . . . . .
H3C H 0.2124 0.0063 -0.0511 0.056 Uiso 1 1 calc R U . . .
H3D H 0.1400 0.0124 -0.0139 0.056 Uiso 1 1 calc R U . . .
H3E H 0.2204 -0.0625 0.0377 0.056 Uiso 1 1 calc R U . . .
C24 C 0.3043(2) 0.5576(5) 0.9767(2) 0.0406(10) Uani 1 1 d . . . . .
H24A H 0.3017 0.4598 0.9475 0.061 Uiso 1 1 calc R U . . .
H24B H 0.2962 0.5387 1.0302 0.061 Uiso 1 1 calc R U . . .
H24C H 0.3554 0.6048 0.9839 0.061 Uiso 1 1 calc R U . . .
C2 C 0.0551(2) -0.0313(4) 0.1123(2) 0.0417(10) Uani 1 1 d . . . . .
H2A H 0.0245 -0.0776 0.0611 0.063 Uiso 1 1 calc R U . . .
H2B H 0.0213 -0.0113 0.1473 0.063 Uiso 1 1 calc R U . . .
H2C H 0.0967 -0.1021 0.1401 0.063 Uiso 1 1 calc R U . . .
C1 C 0.0985(2) 0.2258(5) 0.3366(2) 0.0410(10) Uani 1 1 d . . . . .
H1A H 0.1064 0.3374 0.3357 0.061 Uiso 1 1 calc R U . . .
H1B H 0.1389 0.1804 0.3818 0.061 Uiso 1 1 calc R U . . .
H1C H 0.0473 0.2046 0.3440 0.061 Uiso 1 1 calc R U . . .
C23 C 0.0707(2) 0.6985(5) 0.8505(3) 0.0436(10) Uani 1 1 d . . . . .
H23A H 0.0543 0.6312 0.8028 0.065 Uiso 1 1 calc R U . . .
H23B H 0.0247 0.7391 0.8637 0.065 Uiso 1 1 calc R U . . .
H23C H 0.1023 0.6396 0.8970 0.065 Uiso 1 1 calc R U . . .
C22 C 0.1057(2) 0.9612(5) 0.5944(2) 0.0424(10) Uani 1 1 d . . . . .
H22A H 0.1035 0.8692 0.5607 0.064 Uiso 1 1 calc R U . . .
H22B H 0.1512 1.0229 0.5937 0.064 Uiso 1 1 calc R U . . .
H22C H 0.0585 1.0224 0.5727 0.064 Uiso 1 1 calc R U . . .
H4A H 0.490(2) 0.023(4) 0.422(2) 0.033(10) Uiso 1 1 d . . . . .
H3A H 0.510(2) 0.243(5) 0.675(3) 0.055(13) Uiso 1 1 d . . . . .
H4B H 0.4449(19) 0.098(4) 0.342(2) 0.024(10) Uiso 1 1 d . . . . .
H3B H 0.468(3) 0.408(6) 0.689(3) 0.082(16) Uiso 1 1 d . . . . .
H1 H 0.396(2) 0.536(5) 0.564(3) 0.066(15) Uiso 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
O4 C15 1.276(4) . ?
O2 C6 1.391(4) . ?
O2 C2 1.449(4) . ?
O1 C7 1.395(4) . ?
O1 C3 1.448(4) . ?
O3 C5 1.380(4) . ?
O3 C1 1.433(4) . ?
O5 C15 1.274(4) . ?
O8 C18 1.376(4) . ?
O8 C24 1.442(4) . ?
O6 C20 1.384(4) . ?
O6 C22 1.434(4) . ?
O7 C19 1.391(4) . ?
O7 C23 1.452(5) . ?
N1 C14 1.375(4) . ?
N1 C13 1.361(4) . ?
N1 H1 0.91(5) . ?
N2 C13 1.347(4) . ?
N2 C12 1.366(4) . ?
N3 C13 1.344(4) . ?
N3 H3A 0.89(4) . ?
N3 H3B 1.01(5) . ?
N4 C12 1.340(4) . ?
N4 H4A 0.91(4) . ?
N4 H4B 0.85(3) . ?
C15 C16 1.526(5) . ?
C9 C4 1.399(5) . ?
C9 C8 1.396(5) . ?
C9 C10 1.531(4) . ?
C14 H14 0.9300 . ?
C14 C11 1.361(5) . ?
C16 C17 1.394(5) . ?
C16 C21 1.408(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.407(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.399(5) . ?
C6 C7 1.397(5) . ?
C6 C5 1.418(5) . ?
C11 C12 1.438(5) . ?
C11 C10 1.517(4) . ?
C20 C21 1.392(5) . ?
C20 C19 1.406(5) . ?
C21 H21 0.9300 . ?
C18 C19 1.406(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 H3C 0.9600 . ?
C3 H3D 0.9600 . ?
C3 H3E 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C2 117.0(3) . . ?
C7 O1 C3 116.5(3) . . ?
C5 O3 C1 117.6(3) . . ?
C18 O8 C24 117.4(3) . . ?
C20 O6 C22 117.4(3) . . ?
C19 O7 C23 115.2(3) . . ?
C14 N1 H1 117(3) . . ?
C13 N1 C14 119.1(3) . . ?
C13 N1 H1 124(3) . . ?
C13 N2 C12 117.4(3) . . ?
C13 N3 H3A 119(3) . . ?
C13 N3 H3B 123(3) . . ?
H3A N3 H3B 118(4) . . ?
C12 N4 H4A 119(2) . . ?
C12 N4 H4B 124(2) . . ?
H4A N4 H4B 116(3) . . ?
O4 C15 C16 118.7(3) . . ?
O5 C15 O4 124.2(3) . . ?
O5 C15 C16 117.1(3) . . ?
C4 C9 C10 122.2(3) . . ?
C8 C9 C4 118.6(3) . . ?
C8 C9 C10 118.9(3) . . ?
N1 C14 H14 118.9 . . ?
C11 C14 N1 122.3(3) . . ?
C11 C14 H14 118.9 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 C21 120.0(3) . . ?
C21 C16 C15 120.2(3) . . ?
N2 C13 N1 122.9(3) . . ?
N3 C13 N1 117.3(3) . . ?
N3 C13 N2 119.8(3) . . ?
C9 C4 H4 119.7 . . ?
C5 C4 C9 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C9 C8 H8 119.4 . . ?
C9 C8 C7 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
O2 C6 C7 119.8(3) . . ?
O2 C6 C5 121.5(3) . . ?
C7 C6 C5 118.2(3) . . ?
C14 C11 C12 115.4(3) . . ?
C14 C11 C10 121.4(3) . . ?
C12 C11 C10 123.1(3) . . ?
N2 C12 C11 122.8(3) . . ?
N4 C12 N2 115.6(3) . . ?
N4 C12 C11 121.7(3) . . ?
O1 C7 C8 116.5(3) . . ?
O1 C7 C6 122.6(3) . . ?
C6 C7 C8 120.6(3) . . ?
O3 C5 C4 124.6(3) . . ?
O3 C5 C6 114.7(3) . . ?
C4 C5 C6 120.6(3) . . ?
O6 C20 C21 124.4(3) . . ?
O6 C20 C19 115.2(3) . . ?
C21 C20 C19 120.4(3) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
O8 C18 C17 123.8(3) . . ?
O8 C18 C19 116.4(3) . . ?
C19 C18 C17 119.8(3) . . ?
C9 C10 H10A 107.9 . . ?
C9 C10 H10B 107.9 . . ?
C11 C10 C9 117.8(3) . . ?
C11 C10 H10A 107.9 . . ?
C11 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
O7 C19 C20 118.9(3) . . ?
O7 C19 C18 121.5(3) . . ?
C18 C19 C20 119.6(3) . . ?
O1 C3 H3C 109.5 . . ?
O1 C3 H3D 109.5 . . ?
O1 C3 H3E 109.5 . . ?
H3C C3 H3D 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C15 C16 C17 -7.9(5) . . . . ?
O4 C15 C16 C21 174.9(3) . . . . ?
O2 C6 C7 O1 -3.6(5) . . . . ?
O2 C6 C7 C8 170.0(3) . . . . ?
O2 C6 C5 O3 7.2(5) . . . . ?
O2 C6 C5 C4 -170.4(3) . . . . ?
O5 C15 C16 C17 171.7(3) . . . . ?
O5 C15 C16 C21 -5.6(5) . . . . ?
O8 C18 C19 O7 -0.9(5) . . . . ?
O8 C18 C19 C20 177.9(3) . . . . ?
O6 C20 C21 C16 -178.0(3) . . . . ?
O6 C20 C19 O7 -1.3(5) . . . . ?
O6 C20 C19 C18 179.8(3) . . . . ?
N1 C14 C11 C12 0.9(5) . . . . ?
N1 C14 C11 C10 -176.2(3) . . . . ?
C15 C16 C17 C18 -175.9(3) . . . . ?
C15 C16 C21 C20 175.8(3) . . . . ?
C9 C4 C5 O3 -177.2(3) . . . . ?
C9 C4 C5 C6 0.2(5) . . . . ?
C9 C8 C7 O1 174.9(3) . . . . ?
C9 C8 C7 C6 0.9(5) . . . . ?
C14 N1 C13 N2 -2.4(5) . . . . ?
C14 N1 C13 N3 177.7(3) . . . . ?
C14 C11 C12 N2 -1.3(5) . . . . ?
C14 C11 C12 N4 179.0(3) . . . . ?
C14 C11 C10 C9 -103.2(4) . . . . ?
C16 C17 C18 O8 -179.5(3) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C13 N1 C14 C11 0.8(5) . . . . ?
C13 N2 C12 N4 179.6(3) . . . . ?
C13 N2 C12 C11 -0.1(5) . . . . ?
C4 C9 C8 C7 1.2(5) . . . . ?
C4 C9 C10 C11 31.3(5) . . . . ?
C17 C16 C21 C20 -1.4(5) . . . . ?
C17 C18 C19 O7 179.3(3) . . . . ?
C17 C18 C19 C20 -1.9(5) . . . . ?
C8 C9 C4 C5 -1.8(5) . . . . ?
C8 C9 C10 C11 -154.4(3) . . . . ?
C12 N2 C13 N1 2.0(5) . . . . ?
C12 N2 C13 N3 -178.1(3) . . . . ?
C12 C11 C10 C9 79.8(4) . . . . ?
C7 C6 C5 O3 179.5(3) . . . . ?
C7 C6 C5 C4 1.9(5) . . . . ?
C5 C6 C7 O1 -176.0(3) . . . . ?
C5 C6 C7 C8 -2.4(5) . . . . ?
C21 C16 C17 C18 1.3(5) . . . . ?
C21 C20 C19 O7 -179.3(3) . . . . ?
C21 C20 C19 C18 1.9(5) . . . . ?
C10 C9 C4 C5 172.5(3) . . . . ?
C10 C9 C8 C7 -173.3(3) . . . . ?
C10 C11 C12 N2 175.8(3) . . . . ?
C10 C11 C12 N4 -3.8(5) . . . . ?
C19 C20 C21 C16 -0.2(5) . . . . ?
C3 O1 C7 C8 132.7(3) . . . . ?
C3 O1 C7 C6 -53.5(4) . . . . ?
C24 O8 C18 C17 -7.7(5) . . . . ?
C24 O8 C18 C19 172.5(3) . . . . ?
C2 O2 C6 C7 124.5(4) . . . . ?
C2 O2 C6 C5 -63.3(4) . . . . ?
C1 O3 C5 C4 13.6(5) . . . . ?
C1 O3 C5 C6 -163.9(3) . . . . ?
C23 O7 C19 C20 116.0(4) . . . . ?
C23 O7 C19 C18 -65.2(4) . . . . ?
C22 O6 C20 C21 -0.3(5) . . . . ?
C22 O6 C20 C19 -178.2(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 3.158
_oxdiff_exptl_absorpt_empirical_full_min 0.525
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_r20230402b_autored
_database_code_depnum_ccdc_archive 'CCDC 2283958'
loop_
_audit_author_name
_audit_author_address
'Liang Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2024-05-19 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N4 O3, C7 H5 O4, C2 H3 N'
_chemical_formula_sum            'C23 H27 N5 O7'
_chemical_formula_weight         485.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.0964(3)
_cell_length_b                   9.7449(2)
_cell_length_c                   20.4019(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.150(2)
_cell_angle_gamma                90
_cell_volume                     2359.54(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9347
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.2820
_cell_measurement_theta_min      2.0330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            50758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.454
_diffrn_reflns_theta_min         1.716
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   0.50    0.50    --  -30.00   0.00 180.00  360
  2  ω    -62.00  60.00   0.50    0.50    --  -30.00  70.00 180.00  244
  3  ω    -62.00  60.00   0.50    0.50    --  -30.00  70.00  90.00  244
  4  ω   -120.00  20.00   0.50    0.50    --  -30.00   0.00  90.00  280
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0094468000
_diffrn_orient_matrix_UB_12      0.0717674000
_diffrn_orient_matrix_UB_13      -0.0028261000
_diffrn_orient_matrix_UB_21      0.0112648000
_diffrn_orient_matrix_UB_22      0.0058140000
_diffrn_orient_matrix_UB_23      0.0353258000
_diffrn_orient_matrix_UB_31      0.0579237000
_diffrn_orient_matrix_UB_32      0.0105792000
_diffrn_orient_matrix_UB_33      -0.0002819000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6581
_reflns_number_total             11282
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.071
_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     348
_refine_ls_number_reflns         11282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1613
_refine_ls_R_factor_gt           0.0944
_refine_ls_restrained_S_all      1.062
_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)+(0.0644P)²+1.3740P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.2138
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C11(H11), C15(H15), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.09539(11) 0.71492(14) 0.45957(7) 0.0352(3) Uani 1 1 d . . . . .
O2 O -0.06715(10) 0.81720(13) 0.58369(7) 0.0317(3) Uani 1 1 d . . . . .
O3 O 0.11769(11) 0.96268(14) 0.63661(7) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.49875(12) 0.70323(15) 0.51374(8) 0.0268(3) Uani 1 1 d . . . . .
N2 N 0.57297(12) 0.84714(16) 0.44029(8) 0.0290(3) Uani 1 1 d . . . . .
N3 N 0.68575(14) 0.69141(19) 0.50755(9) 0.0357(4) Uani 1 1 d . . . . .
N4 N 0.46040(15) 1.00108(18) 0.37501(9) 0.0335(4) Uani 1 1 d . . . . .
C1 C 0.58549(14) 0.74809(18) 0.48641(9) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.47027(14) 0.90256(18) 0.42133(9) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.37521(14) 0.86225(17) 0.44916(9) 0.0253(3) Uani 1 1 d . . . . .
C4 C 0.39510(14) 0.76087(18) 0.49515(9) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.3363 0.7297 0.5146 0.032 Uiso 1 1 calc R U . . .
C24 C 0.26155(14) 0.92882(19) 0.42683(9) 0.0284(3) Uani 1 1 d . . . . .
H24A H 0.2318 0.9019 0.3810 0.034 Uiso 1 1 calc R U . . .
H24B H 0.2714 1.0276 0.4274 0.034 Uiso 1 1 calc R U . . .
C6 C 0.17623(14) 0.89252(17) 0.46918(9) 0.0261(3) Uani 1 1 d . . . . .
C7 C 0.19089(14) 0.94277(18) 0.53388(9) 0.0266(3) Uani 1 1 d . . . . .
H7 H 0.2541 0.9951 0.5512 0.032 Uiso 1 1 calc R U . . .
C8 C 0.11118(14) 0.91496(17) 0.57289(9) 0.0259(3) Uani 1 1 d . . . . .
C9 C 0.01559(14) 0.83744(17) 0.54651(9) 0.0269(3) Uani 1 1 d . . . . .
C10 C 0.00243(14) 0.78716(17) 0.48175(10) 0.0279(4) Uani 1 1 d . . . . .
C11 C 0.08252(14) 0.81306(18) 0.44281(10) 0.0287(4) Uani 1 1 d . . . . .
H11 H 0.0737 0.7778 0.3997 0.034 Uiso 1 1 calc R U . . .
C12 C -0.10362(19) 0.6414(3) 0.39838(14) 0.0535(7) Uani 1 1 d . . . . .
H12A H -0.1058 0.7051 0.3623 0.080 Uiso 1 1 calc R U . . .
H12B H -0.1712 0.5872 0.3906 0.080 Uiso 1 1 calc R U . . .
H12C H -0.0394 0.5822 0.4010 0.080 Uiso 1 1 calc R U . . .
C13 C -0.06419(18) 0.6830(2) 0.61256(12) 0.0420(5) Uani 1 1 d . . . . .
H13A H -0.0738 0.6153 0.5777 0.063 Uiso 1 1 calc R U . . .
H13B H -0.1238 0.6744 0.6372 0.063 Uiso 1 1 calc R U . . .
H13C H 0.0070 0.6692 0.6421 0.063 Uiso 1 1 calc R U . . .
C14 C 0.21886(17) 1.0330(2) 0.66607(10) 0.0359(4) Uani 1 1 d . . . . .
H14A H 0.2288 1.1114 0.6393 0.054 Uiso 1 1 calc R U . . .
H14B H 0.2820 0.9722 0.6684 0.054 Uiso 1 1 calc R U . . .
H14C H 0.2138 1.0625 0.7103 0.054 Uiso 1 1 calc R U . . .
O4 O 0.66745(13) 0.08235(16) 0.84696(9) 0.0445(4) Uani 1 1 d . . . . .
O5 O 0.82092(11) 0.33407(16) 0.68980(8) 0.0392(3) Uani 1 1 d . . . . .
O6 O 0.69704(12) 0.48701(15) 0.60882(8) 0.0372(3) Uani 1 1 d . . . . .
O7 O 0.51507(11) 0.51123(14) 0.61014(7) 0.0334(3) Uani 1 1 d . . . . .
C15 C 0.53179(15) 0.32058(18) 0.71784(9) 0.0285(4) Uani 1 1 d . . . . .
H15 H 0.4612 0.3580 0.7013 0.034 Uiso 1 1 calc R U . . .
C16 C 0.54320(15) 0.22923(19) 0.77025(10) 0.0298(4) Uani 1 1 d . . . . .
H16 H 0.4813 0.2054 0.7887 0.036 Uiso 1 1 calc R U . . .
C17 C 0.64958(16) 0.17261(19) 0.79546(10) 0.0320(4) Uani 1 1 d . . . . .
C18 C 0.74082(15) 0.2095(2) 0.76796(11) 0.0356(4) Uani 1 1 d . . . . .
H18 H 0.8113 0.1724 0.7850 0.043 Uiso 1 1 calc R U . . .
C19 C 0.72873(15) 0.30151(19) 0.71507(10) 0.0304(4) Uani 1 1 d . . . . .
C20 C 0.62283(14) 0.35907(17) 0.68866(9) 0.0265(3) Uani 1 1 d . . . . .
C21 C 0.61035(15) 0.45885(18) 0.63290(9) 0.0287(4) Uani 1 1 d . . . . .
N22 N 0.26525(17) 1.1542(2) 0.28304(12) 0.0552(6) Uani 1 1 d . . . . .
C23 C 0.1771(2) 1.1132(3) 0.27811(13) 0.0575(7) Uani 1 1 d . . . . .
C5 C 0.0591(2) 1.0543(3) 0.27059(13) 0.0552(7) Uani 1 1 d . . . . .
H5A H 0.0071 1.1115 0.2411 0.083 Uiso 1 1 calc R U . . .
H5B H 0.0379 1.0507 0.3135 0.083 Uiso 1 1 calc R U . . .
H5C H 0.0578 0.9633 0.2523 0.083 Uiso 1 1 calc R U . . .
H4A H 0.396(2) 1.036(3) 0.3562(12) 0.040(6) Uiso 1 1 d . . . . .
H4B H 0.519(2) 1.021(2) 0.3569(12) 0.041(6) Uiso 1 1 d . . . . .
H3A H 0.692(2) 0.625(3) 0.5404(13) 0.052(7) Uiso 1 1 d . . . . .
H3B H 0.746(2) 0.727(3) 0.4933(13) 0.049(7) Uiso 1 1 d . . . . .
H1 H 0.510(2) 0.633(3) 0.5481(14) 0.056(8) Uiso 1 1 d . . . . .
H4C H 0.603(3) 0.054(4) 0.8561(16) 0.080(10) Uiso 1 1 d . . . . .
H5 H 0.792(3) 0.393(4) 0.6537(16) 0.075(10) Uiso 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
O1 C10 1.376(2) . ?
O1 C12 1.426(3) . ?
O2 C9 1.382(2) . ?
O2 C13 1.432(2) . ?
O3 C8 1.369(2) . ?
O3 C14 1.429(2) . ?
N1 C1 1.352(2) . ?
N1 C4 1.359(2) . ?
N1 H1 0.97(3) . ?
N2 C1 1.336(2) . ?
N2 C2 1.341(2) . ?
N3 C1 1.327(2) . ?
N3 H3A 0.93(3) . ?
N3 H3B 0.91(3) . ?
N4 C2 1.336(2) . ?
N4 H4A 0.87(3) . ?
N4 H4B 0.88(3) . ?
C2 C3 1.432(2) . ?
C3 C4 1.352(2) . ?
C3 C24 1.509(2) . ?
C4 H4 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C6 1.511(2) . ?
C6 C7 1.387(3) . ?
C6 C11 1.392(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.389(3) . ?
C10 C11 1.390(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O4 C17 1.355(2) . ?
O4 H4C 0.88(3) . ?
O5 C19 1.354(2) . ?
O5 H5 0.95(3) . ?
O6 C21 1.271(2) . ?
O7 C21 1.264(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(3) . ?
C15 C20 1.400(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.403(2) . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(3) . ?
C19 C20 1.407(2) . ?
C20 C21 1.482(3) . ?
N22 C23 1.125(3) . ?
C23 C5 1.518(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C12 117.06(16) . . ?
C9 O2 C13 113.14(15) . . ?
C8 O3 C14 116.71(14) . . ?
C1 N1 C4 119.91(16) . . ?
C1 N1 H1 120.9(16) . . ?
C4 N1 H1 119.2(16) . . ?
C1 N2 C2 117.81(15) . . ?
C1 N3 H3A 117.8(16) . . ?
C1 N3 H3B 118.8(17) . . ?
H3A N3 H3B 123(2) . . ?
C2 N4 H4A 122.9(16) . . ?
C2 N4 H4B 119.1(16) . . ?
H4A N4 H4B 117(2) . . ?
N2 C1 N1 122.18(16) . . ?
N3 C1 N1 117.70(17) . . ?
N3 C1 N2 120.11(17) . . ?
N2 C2 C3 123.03(16) . . ?
N4 C2 N2 116.38(16) . . ?
N4 C2 C3 120.58(16) . . ?
C2 C3 C24 121.12(16) . . ?
C4 C3 C2 115.27(16) . . ?
C4 C3 C24 123.60(16) . . ?
N1 C4 H4 119.1 . . ?
C3 C4 N1 121.77(16) . . ?
C3 C4 H4 119.1 . . ?
C3 C24 H24A 108.7 . . ?
C3 C24 H24B 108.7 . . ?
C3 C24 C6 114.20(15) . . ?
H24A C24 H24B 107.6 . . ?
C6 C24 H24A 108.7 . . ?
C6 C24 H24B 108.7 . . ?
C7 C6 C24 119.08(15) . . ?
C7 C6 C11 120.60(17) . . ?
C11 C6 C24 120.29(16) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.06(16) . . ?
C8 C7 H7 120.0 . . ?
O3 C8 C7 123.96(15) . . ?
O3 C8 C9 116.13(16) . . ?
C7 C8 C9 119.88(16) . . ?
O2 C9 C8 119.90(16) . . ?
O2 C9 C10 120.65(15) . . ?
C10 C9 C8 119.38(16) . . ?
O1 C10 C9 115.24(16) . . ?
O1 C10 C11 123.72(17) . . ?
C9 C10 C11 121.02(16) . . ?
C6 C11 H11 120.5 . . ?
C10 C11 C6 119.05(17) . . ?
C10 C11 H11 120.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 O4 H4C 111(2) . . ?
C19 O5 H5 103.3(19) . . ?
C16 C15 H15 118.9 . . ?
C16 C15 C20 122.27(16) . . ?
C20 C15 H15 118.9 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.07(18) . . ?
C17 C16 H16 120.5 . . ?
O4 C17 C16 122.48(18) . . ?
O4 C17 C18 117.68(17) . . ?
C18 C17 C16 119.84(18) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.82(17) . . ?
C19 C18 H18 119.6 . . ?
O5 C19 C18 118.46(17) . . ?
O5 C19 C20 121.13(18) . . ?
C18 C19 C20 120.41(17) . . ?
C15 C20 C19 117.59(17) . . ?
C15 C20 C21 122.03(16) . . ?
C19 C20 C21 120.37(16) . . ?
O6 C21 C20 117.98(16) . . ?
O7 C21 O6 122.18(18) . . ?
O7 C21 C20 119.83(16) . . ?
N22 C23 C5 178.4(3) . . ?
C23 C5 H5A 109.5 . . ?
C23 C5 H5B 109.5 . . ?
C23 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 C6 177.16(16) . . . . ?
O2 C9 C10 O1 -1.6(2) . . . . ?
O2 C9 C10 C11 176.68(15) . . . . ?
O3 C8 C9 O2 2.2(2) . . . . ?
O3 C8 C9 C10 179.12(15) . . . . ?
N2 C2 C3 C4 -1.7(3) . . . . ?
N2 C2 C3 C24 179.24(16) . . . . ?
N4 C2 C3 C4 179.48(16) . . . . ?
N4 C2 C3 C24 0.4(3) . . . . ?
C1 N1 C4 C3 0.6(3) . . . . ?
C1 N2 C2 N4 -179.83(16) . . . . ?
C1 N2 C2 C3 1.3(3) . . . . ?
C2 N2 C1 N1 0.1(3) . . . . ?
C2 N2 C1 N3 -179.01(17) . . . . ?
C2 C3 C4 N1 0.7(2) . . . . ?
C2 C3 C24 C6 -169.93(15) . . . . ?
C3 C24 C6 C7 69.7(2) . . . . ?
C3 C24 C6 C11 -112.16(18) . . . . ?
C4 N1 C1 N2 -1.1(3) . . . . ?
C4 N1 C1 N3 178.10(17) . . . . ?
C4 C3 C24 C6 11.1(2) . . . . ?
C24 C3 C4 N1 179.76(16) . . . . ?
C24 C6 C7 C8 177.57(15) . . . . ?
C24 C6 C11 C10 -176.71(16) . . . . ?
C6 C7 C8 O3 -178.59(15) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C7 C6 C11 C10 1.4(3) . . . . ?
C7 C8 C9 O2 -175.85(15) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C8 C9 C10 O1 -178.51(15) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C6 -1.0(3) . . . . ?
C11 C6 C7 C8 -0.5(3) . . . . ?
C12 O1 C10 C9 -169.33(19) . . . . ?
C12 O1 C10 C11 12.4(3) . . . . ?
C13 O2 C9 C8 -103.50(19) . . . . ?
C13 O2 C9 C10 79.6(2) . . . . ?
C14 O3 C8 C7 -6.7(2) . . . . ?
C14 O3 C8 C9 175.32(15) . . . . ?
O4 C17 C18 C19 179.99(18) . . . . ?
O5 C19 C20 C15 -179.69(16) . . . . ?
O5 C19 C20 C21 -0.9(3) . . . . ?
C15 C16 C17 O4 179.87(18) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C15 C20 C21 O6 -179.26(17) . . . . ?
C15 C20 C21 O7 -0.4(3) . . . . ?
C16 C15 C20 C19 -0.4(3) . . . . ?
C16 C15 C20 C21 -179.15(17) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 O5 -179.84(18) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C18 C19 C20 C21 179.06(17) . . . . ?
C19 C20 C21 O6 2.0(2) . . . . ?
C19 C20 C21 O7 -179.10(16) . . . . ?
C20 C15 C16 C17 0.1(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 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.605
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_r20230529c_autored
_database_code_depnum_ccdc_archive 'CCDC 2283930'
loop_
_audit_author_name
_audit_author_address
'Zhang liang'
;Tianjin University
China
;
_audit_update_record             
;
2023-07-24 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 O6 S2, 2(C14 H19 N4 O3)'
_chemical_formula_sum            'C38 H44 N8 O12 S2'
_chemical_formula_weight         868.93
_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'
S S 0.1246 0.1234 '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                   12.2812(2)
_cell_length_b                   11.5143(2)
_cell_length_c                   14.0952(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.887(2)
_cell_angle_gamma                90
_cell_volume                     1896.85(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18902
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.6210
_cell_measurement_theta_min      1.9200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0219
_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       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26794
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         1.928
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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   -110.00  70.00   0.50    1.00    --  -20.00   0.00   0.00  360
  2  ω    -47.00  70.00   0.50    1.00    --  -20.00  70.00 180.00  234
  3  ω    -88.00  -1.00   0.50    1.00    --  -20.00 -70.00 180.00  174
  4  ω   -110.00 -17.00   0.50    1.00    --  -20.00 -70.00  90.00  186
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0522083000
_diffrn_orient_matrix_UB_12      -0.0136455000
_diffrn_orient_matrix_UB_13      0.0370715000
_diffrn_orient_matrix_UB_21      0.0262705000
_diffrn_orient_matrix_UB_22      -0.0097232000
_diffrn_orient_matrix_UB_23      -0.0376179000
_diffrn_orient_matrix_UB_31      0.0163403000
_diffrn_orient_matrix_UB_32      0.0592963000
_diffrn_orient_matrix_UB_33      0.0023612000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'roting anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4838
_reflns_number_total             5310
_reflns_odcompleteness_completeness 93.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     34.68
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.009
_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)+(0.0542P)²+0.8911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
1.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C4(H4A), C7(H7), C11(H11)
1.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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
S1 S 0.76359(2) 0.01022(2) 0.45984(2) 0.01280(8) Uani 1 1 d . . . . .
O4 O 0.74728(7) 0.13220(7) 0.42917(6) 0.01661(17) Uani 1 1 d . . . . .
O5 O 0.87389(7) -0.00978(8) 0.53426(6) 0.01813(18) Uani 1 1 d . . . . .
O6 O 0.74216(7) -0.06813(7) 0.37465(6) 0.01637(17) Uani 1 1 d . . . . .
C15 C 0.65785(9) -0.01819(10) 0.52009(8) 0.0124(2) Uani 1 1 d . . . . .
C16 C 0.69514(9) -0.05968(10) 0.61589(8) 0.0146(2) Uani 1 1 d . . . . .
H16 H 0.773809 -0.076991 0.646316 0.018 Uiso 1 1 calc R U . . .
C17 C 0.61590(10) -0.07647(10) 0.66895(8) 0.0155(2) Uani 1 1 d . . . . .
H17 H 0.642047 -0.104462 0.735527 0.019 Uiso 1 1 calc R U . . .
C18 C 0.50187(9) -0.05311(10) 0.62614(8) 0.0142(2) Uani 1 1 d . . . . .
H18 H 0.449924 -0.066678 0.662884 0.017 Uiso 1 1 calc R U . . .
C19 C 0.53958(9) 0.00882(9) 0.47257(8) 0.0120(2) Uani 1 1 d . . . . .
O1 O 0.43369(7) 0.64218(8) 0.56163(6) 0.01865(18) Uani 1 1 d . . . . .
O2 O 0.37003(7) 0.65477(7) 0.36148(6) 0.01609(17) Uani 1 1 d . . . . .
O3 O 0.52494(7) 0.66970(8) 0.26377(6) 0.01958(18) Uani 1 1 d . . . . .
N1 N 1.03186(9) 0.18661(10) 0.59042(8) 0.0196(2) Uani 1 1 d . . . . .
H1A H 1.1060(15) 0.1749(15) 0.6146(13) 0.025(4) Uiso 1 1 d . . . . .
H1B H 0.9871(16) 0.1295(17) 0.5612(14) 0.033(5) Uiso 1 1 d . . . . .
N2 N 1.07563(9) 0.57089(10) 0.68332(8) 0.0191(2) Uani 1 1 d . . . . .
H2A H 1.1384(16) 0.5503(16) 0.7278(13) 0.029(4) Uiso 1 1 d . . . . .
H2B H 1.0435(16) 0.6371(17) 0.6935(14) 0.033(5) Uiso 1 1 d . . . . .
N3 N 1.05545(8) 0.37935(9) 0.63760(7) 0.01559(19) Uani 1 1 d . . . . .
N4 N 0.87601(8) 0.30871(9) 0.54036(7) 0.01496(19) Uani 1 1 d . . . . .
H4 H 0.8338(14) 0.2510(15) 0.5062(12) 0.023(4) Uiso 1 1 d . . . . .
C1 C 0.98872(9) 0.29262(10) 0.59005(8) 0.0147(2) Uani 1 1 d . . . . .
C2 C 1.00844(9) 0.48516(10) 0.63383(8) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.89057(9) 0.50886(10) 0.58038(8) 0.0135(2) Uani 1 1 d . . . . .
C4 C 0.82764(9) 0.41637(10) 0.53564(8) 0.0147(2) Uani 1 1 d . . . . .
H4A H 0.748756 0.426352 0.500465 0.018 Uiso 1 1 calc R U . . .
C5 C 0.84216(9) 0.62977(10) 0.57895(9) 0.0158(2) Uani 1 1 d . . . . .
H5A H 0.853595 0.655101 0.648457 0.019 Uiso 1 1 calc R U . . .
H5B H 0.885419 0.683629 0.549161 0.019 Uiso 1 1 calc R U . . .
C6 C 0.71660(9) 0.63870(10) 0.52144(9) 0.0144(2) Uani 1 1 d . . . . .
C7 C 0.63556(10) 0.63509(10) 0.57208(8) 0.0151(2) Uani 1 1 d . . . . .
H7 H 0.659238 0.627222 0.642567 0.018 Uiso 1 1 calc R U . . .
C8 C 0.51978(10) 0.64304(10) 0.51909(9) 0.0141(2) Uani 1 1 d . . . . .
C9 C 0.48498(9) 0.65232(10) 0.41526(8) 0.0136(2) Uani 1 1 d . . . . .
C10 C 0.56693(9) 0.65678(10) 0.36524(8) 0.0144(2) Uani 1 1 d . . . . .
C11 C 0.68304(9) 0.64917(10) 0.41817(9) 0.0154(2) Uani 1 1 d . . . . .
H11 H 0.738726 0.651111 0.384008 0.018 Uiso 1 1 calc R U . . .
C12 C 0.46503(11) 0.64010(12) 0.66780(9) 0.0208(2) Uani 1 1 d . . . . .
H12A H 0.395876 0.642730 0.688552 0.031 Uiso 1 1 calc R U . . .
H12B H 0.513224 0.707513 0.695013 0.031 Uiso 1 1 calc R U . . .
H12C H 0.507525 0.568649 0.692781 0.031 Uiso 1 1 calc R U . . .
C13 C 0.32642(10) 0.77064(11) 0.35264(9) 0.0195(2) Uani 1 1 d . . . . .
H13A H 0.247142 0.771112 0.308793 0.029 Uiso 1 1 calc R U . . .
H13B H 0.373193 0.820652 0.324398 0.029 Uiso 1 1 calc R U . . .
H13C H 0.329029 0.799639 0.418669 0.029 Uiso 1 1 calc R U . . .
C14 C 0.60025(11) 0.63802(11) 0.20798(9) 0.0207(2) Uani 1 1 d . . . . .
H14A H 0.557842 0.638141 0.136651 0.031 Uiso 1 1 calc R U . . .
H14B H 0.631196 0.560232 0.227980 0.031 Uiso 1 1 calc R U . . .
H14C H 0.663227 0.694040 0.221153 0.031 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
S1 O4 1.4652(9) . ?
S1 O5 1.4545(9) . ?
S1 O6 1.4598(9) . ?
S1 C15 1.7866(11) . ?
C15 C16 1.3717(15) . ?
C15 C19 1.4344(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.4110(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.3706(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.4213(15) 3_656 ?
C19 C19 1.430(2) 3_656 ?
O1 C8 1.3663(13) . ?
O1 C12 1.4263(14) . ?
O2 C9 1.3824(13) . ?
O2 C13 1.4288(14) . ?
O3 C10 1.3714(14) . ?
O3 C14 1.4330(14) . ?
N1 H1A 0.879(18) . ?
N1 H1B 0.87(2) . ?
N1 C1 1.3300(16) . ?
N2 H2A 0.864(19) . ?
N2 H2B 0.89(2) . ?
N2 C2 1.3372(15) . ?
N3 C1 1.3344(15) . ?
N3 C2 1.3423(15) . ?
N4 H4 0.888(18) . ?
N4 C1 1.3585(14) . ?
N4 C4 1.3674(15) . ?
C2 C3 1.4379(15) . ?
C3 C4 1.3527(16) . ?
C3 C5 1.5116(16) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5092(15) . ?
C6 C7 1.3921(15) . ?
C6 C11 1.3909(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3913(15) . ?
C8 C9 1.3971(16) . ?
C9 C10 1.3958(15) . ?
C10 C11 1.3943(15) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
O4 S1 C15 105.21(5) . . ?
O5 S1 O4 112.16(5) . . ?
O5 S1 O6 112.84(5) . . ?
O5 S1 C15 106.27(5) . . ?
O6 S1 O4 112.09(5) . . ?
O6 S1 C15 107.71(5) . . ?
C16 C15 S1 117.38(8) . . ?
C16 C15 C19 121.28(10) . . ?
C19 C15 S1 121.20(8) . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.56(10) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.17(10) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.77(10) . 3_656 ?
C19 C18 H18 119.6 3_656 . ?
C18 C19 C15 122.80(9) 3_656 . ?
C18 C19 C19 118.80(12) 3_656 3_656 ?
C19 C19 C15 118.40(12) 3_656 . ?
C8 O1 C12 117.69(9) . . ?
C9 O2 C13 111.04(9) . . ?
C10 O3 C14 116.45(9) . . ?
H1A N1 H1B 119.5(16) . . ?
C1 N1 H1A 120.5(12) . . ?
C1 N1 H1B 119.8(12) . . ?
H2A N2 H2B 117.3(17) . . ?
C2 N2 H2A 116.5(12) . . ?
C2 N2 H2B 118.9(12) . . ?
C1 N3 C2 117.97(10) . . ?
C1 N4 H4 120.7(11) . . ?
C1 N4 C4 120.49(10) . . ?
C4 N4 H4 118.6(11) . . ?
N1 C1 N3 120.16(10) . . ?
N1 C1 N4 117.96(11) . . ?
N3 C1 N4 121.89(11) . . ?
N2 C2 N3 117.41(10) . . ?
N2 C2 C3 119.59(11) . . ?
N3 C2 C3 122.99(10) . . ?
C2 C3 C5 120.69(10) . . ?
C4 C3 C2 115.72(10) . . ?
C4 C3 C5 123.56(10) . . ?
N4 C4 H4A 119.5 . . ?
C3 C4 N4 120.90(10) . . ?
C3 C4 H4A 119.5 . . ?
C3 C5 H5A 108.8 . . ?
C3 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C3 113.75(9) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C7 C6 C5 119.74(10) . . ?
C11 C6 C5 119.57(10) . . ?
C11 C6 C7 120.69(10) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.77(10) . . ?
C8 C7 H7 120.1 . . ?
O1 C8 C7 124.40(10) . . ?
O1 C8 C9 115.55(10) . . ?
C7 C8 C9 120.04(10) . . ?
O2 C9 C8 120.55(10) . . ?
O2 C9 C10 119.71(10) . . ?
C10 C9 C8 119.73(10) . . ?
O3 C10 C9 115.62(10) . . ?
O3 C10 C11 124.06(10) . . ?
C11 C10 C9 120.33(10) . . ?
C6 C11 C10 119.41(10) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C15 C16 C17 175.98(9) . . . . ?
S1 C15 C19 C18 3.61(15) . . . 3_656 ?
S1 C15 C19 C19 -175.88(10) . . . 3_656 ?
O4 S1 C15 C16 -123.89(9) . . . . ?
O4 S1 C15 C19 51.97(10) . . . . ?
O5 S1 C15 C16 -4.78(11) . . . . ?
O5 S1 C15 C19 171.08(9) . . . . ?
O6 S1 C15 C16 116.39(9) . . . . ?
O6 S1 C15 C19 -67.75(10) . . . . ?
C15 C16 C17 C18 0.64(18) . . . . ?
C16 C15 C19 C18 179.31(11) . . . 3_656 ?
C16 C15 C19 C19 -0.18(19) . . . 3_656 ?
C16 C17 C18 C19 -1.34(18) . . . 3_656 ?
C19 C15 C16 C17 0.13(17) . . . . ?
O1 C8 C9 O2 -2.87(16) . . . . ?
O1 C8 C9 C10 178.44(10) . . . . ?
O2 C9 C10 O3 3.35(15) . . . . ?
O2 C9 C10 C11 -177.13(10) . . . . ?
O3 C10 C11 C6 178.59(11) . . . . ?
N2 C2 C3 C4 -177.53(10) . . . . ?
N2 C2 C3 C5 0.46(16) . . . . ?
N3 C2 C3 C4 1.85(16) . . . . ?
N3 C2 C3 C5 179.84(10) . . . . ?
C1 N3 C2 N2 178.77(10) . . . . ?
C1 N3 C2 C3 -0.62(16) . . . . ?
C1 N4 C4 C3 -0.17(16) . . . . ?
C2 N3 C1 N1 179.00(11) . . . . ?
C2 N3 C1 N4 -1.10(16) . . . . ?
C2 C3 C4 N4 -1.40(16) . . . . ?
C2 C3 C5 C6 -178.65(10) . . . . ?
C3 C5 C6 C7 97.67(12) . . . . ?
C3 C5 C6 C11 -81.62(13) . . . . ?
C4 N4 C1 N1 -178.56(10) . . . . ?
C4 N4 C1 N3 1.53(16) . . . . ?
C4 C3 C5 C6 -0.82(16) . . . . ?
C5 C3 C4 N4 -179.32(10) . . . . ?
C5 C6 C7 C8 -179.85(10) . . . . ?
C5 C6 C11 C10 179.66(10) . . . . ?
C6 C7 C8 O1 -178.96(10) . . . . ?
C6 C7 C8 C9 1.25(17) . . . . ?
C7 C6 C11 C10 0.38(17) . . . . ?
C7 C8 C9 O2 176.93(10) . . . . ?
C7 C8 C9 C10 -1.75(17) . . . . ?
C8 C9 C10 O3 -177.95(10) . . . . ?
C8 C9 C10 C11 1.56(17) . . . . ?
C9 C10 C11 C6 -0.88(17) . . . . ?
C11 C6 C7 C8 -0.57(17) . . . . ?
C12 O1 C8 C7 4.00(16) . . . . ?
C12 O1 C8 C9 -176.20(10) . . . . ?
C13 O2 C9 C8 87.58(13) . . . . ?
C13 O2 C9 C10 -93.74(12) . . . . ?
C14 O3 C10 C9 -160.76(10) . . . . ?
C14 O3 C10 C11 19.74(16) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.517
_oxdiff_exptl_absorpt_empirical_full_min 0.464
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_p20230804c
_database_code_depnum_ccdc_archive 'CCDC 2288508'
loop_
_audit_author_name
_audit_author_address
'Zhang liang'
;Tianjin University
China
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H2 N2 O4, H2 O, 2(C14 H19 N4 O3)'
_chemical_formula_sum            'C34 H42 N10 O11'
_chemical_formula_weight         766.77
_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                   10.6038(7)
_cell_length_b                   12.9331(11)
_cell_length_c                   14.4781(8)
_cell_angle_alpha                67.818(6)
_cell_angle_beta                 84.598(5)
_cell_angle_gamma                84.690(6)
_cell_volume                     1826.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4392
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.3090
_cell_measurement_theta_min      3.7030
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24796
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.451
_diffrn_reflns_theta_min         3.698
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  92.00   1.00   15.00    --    5.00  38.00 150.00   50
  2  ω     -6.00  20.00   1.00   15.00    --    5.00  38.00 150.00   26
  3  ω    -82.00  21.00   1.00   15.00    --  -49.00  38.00 -90.00  103
  4  ω    -76.00 -24.00   1.00   15.00    --  -49.00 -57.00 -60.00   52
  5  ω   -133.00 -16.00   1.00   15.00    --  -49.00 -38.00  60.00  117
  6  ω     11.00  37.00   1.00   15.00    --  -49.00  67.00 153.41   26
  7  ω    -79.00 -13.00   1.00   15.00    --  -49.00  67.00 153.41   66
  8  ω    -68.00  40.00   1.00   15.00    --  -49.00  69.00 -29.32  108
  9  ω   -140.00-114.00   1.00   19.00    -- -110.00  72.00-180.00   26
 10  ω   -176.00 -80.00   1.00   19.00    -- -110.00 -72.00 120.00   96
 11  ω   -114.00 -21.00   1.00   19.00    -- -110.00  57.00  30.00   93
 12  ω   -199.00 -60.00   1.00   19.00    -- -110.00 -19.00  60.00  139
 13  ω   -101.00 -57.00   1.00   19.00    -- -110.00  72.00 150.00   44
 14  ω    -65.00 -22.00   1.00   19.00    -- -110.00  72.00-180.00   43
 15  ω   -157.00-124.00   1.00   19.00    -- -110.00 -72.00-150.00   33
 16  ω   -144.00 -45.00   1.00   19.00    -- -110.00  72.00  30.00   99
 17  ω   -199.00-168.00   1.00   19.00    -- -110.00 -38.00-180.00   31
 18  ω   -118.00 -92.00   1.00   19.00    -- -110.00  72.00 120.00   26
 19  ω   -196.00 -96.00   1.00   19.00    -- -110.00 -72.00 -30.00  100
 20  ω   -141.00-115.00   1.00   19.00    -- -110.00 -38.00-180.00   26
 21  ω   -104.00 -67.00   1.00   19.00    -- -110.00  72.00 -30.00   37
 22  ω   -122.00 -72.00   1.00   19.00    -- -110.00  72.00-150.00   50
 23  ω   -198.00 -66.00   1.00   19.00    -- -110.00 -19.00   0.00  132
 24  ω   -122.00 -96.00   1.00   19.00    -- -110.00  72.00   0.00   26
 25  ω   -138.00 -21.00   1.00   19.00    -- -110.00  72.00 -90.00  117
 26  ω   -106.00 -60.00   1.00   19.00    -- -110.00  72.00  90.00   46
 27  ω   -101.00 -76.00   1.00   19.00    -- -110.00 -72.00-150.00   25
 28  ω   -184.00-156.00   1.00   19.00    -- -110.00 -19.00-180.00   28
 29  ω   -121.00 -96.00   1.00   19.00    -- -110.00 -19.00-180.00   25
 30  ω   -122.00 -96.00   1.00   19.00    -- -110.00  72.00-120.00   26
 31  ω   -138.00 -34.00   1.00   19.00    -- -110.00  57.00 -90.00  104
 32  ω   -199.00-101.00   1.00   19.00    -- -110.00 -72.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0030584000
_diffrn_orient_matrix_UB_12      0.1259922000
_diffrn_orient_matrix_UB_13      -0.0202655000
_diffrn_orient_matrix_UB_21      0.0248027000
_diffrn_orient_matrix_UB_22      0.0253295000
_diffrn_orient_matrix_UB_23      -0.1127683000
_diffrn_orient_matrix_UB_31      -0.1440606000
_diffrn_orient_matrix_UB_32      0.0097737000
_diffrn_orient_matrix_UB_33      -0.0114812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4918
_reflns_number_total             7566
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.026
_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)+(0.0680P)²+0.9717P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1786
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O004(H00K,H00L)
2.b Secondary CH2 refined with riding coordinates:
 C010(H01L,H01M), C018(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 N00E(H00E), N00F(H00F), C00W(H00W), C00X(H00X), C00Y(H00Y), C012(H012),
 C013(H013), C015(H015), C016(H016), C01D(H01W)
2.d X=CH2 refined with riding coordinates:
 N00I(H00G,H00H), N00J(H00I,H00J), N00K(H00A,H00B), N00L(H00C,H00D)
2.e Idealised Me refined as rotating group:
 C01E(H01N,H01O,H01P), C01F(H01C,H01D,H01E), C01G(H01F,H01G,H01H), C01H(H01Q,
 H01R,H01S), C01I(H01I,H01J,H01K), C01J(H01T,H01U,H01V)
;
_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
O001 O 1.69759(19) 0.64570(16) 0.31315(13) 0.0422(5) Uani 1 1 d . . . . .
O002 O 1.51908(19) 0.56027(17) 0.33383(13) 0.0445(5) Uani 1 1 d . . . . .
O003 O 1.83278(19) 0.84472(17) 0.12671(14) 0.0429(5) Uani 1 1 d . . . . .
O004 O 1.3443(2) 0.64574(17) 0.60283(15) 0.0454(5) Uani 1 1 d G . . . .
H00K H 1.3831 0.6912 0.6179 0.068 Uiso 1 1 d G U . . .
H00L H 1.3881 0.5839 0.6172 0.068 Uiso 1 1 d G U . . .
O005 O 1.3798(2) 1.25399(17) 0.41566(14) 0.0481(5) Uani 1 1 d . . . . .
O006 O 1.0950(2) 1.27290(18) 0.05707(15) 0.0504(5) Uani 1 1 d . . . . .
O007 O 0.8496(2) 1.24855(18) 0.03144(15) 0.0500(5) Uani 1 1 d . . . . .
O008 O 0.6603(2) 1.35695(18) 0.09469(16) 0.0496(5) Uani 1 1 d . . . . .
O009 O 1.6958(2) 0.90126(19) 0.22847(15) 0.0505(5) Uani 1 1 d . . . . .
O00A O 1.1474(2) 1.19930(19) 0.39545(16) 0.0515(5) Uani 1 1 d . . . . .
O00B O 1.5878(2) 1.16877(19) 0.34729(16) 0.0505(5) Uani 1 1 d . . . . .
N00C N 1.1162(2) 1.45087(19) 0.43558(15) 0.0349(5) Uani 1 1 d . . . . .
N00D N 1.1182(2) 0.74834(18) 0.38112(15) 0.0361(5) Uani 1 1 d . . . . .
N00E N 1.2644(2) 1.54627(19) 0.30749(15) 0.0377(5) Uani 1 1 d . . . . .
H00E H 1.3411 1.5653 0.2892 0.045 Uiso 1 1 calc R U . . .
N00F N 1.0237(2) 0.84277(19) 0.22728(15) 0.0381(5) Uani 1 1 d . . . . .
H00F H 0.9615 0.8503 0.1907 0.046 Uiso 1 1 calc R U . . .
N00G N 1.5795(2) 0.88461(19) 0.04013(16) 0.0382(5) Uani 1 1 d . . . . .
N00H N 1.4525(2) 0.6923(2) 0.15095(16) 0.0389(5) Uani 1 1 d . . . . .
N00I N 1.3138(2) 1.47964(19) 0.47173(15) 0.0394(6) Uani 1 1 d . . . . .
H00G H 1.2944 1.4461 0.5345 0.047 Uiso 1 1 calc R U . . .
H00H H 1.3875 1.5057 0.4520 0.047 Uiso 1 1 calc R U . . .
N00J N 0.9207(2) 1.42504(19) 0.39873(15) 0.0378(5) Uani 1 1 d . . . . .
H00I H 0.9056 1.3860 0.4611 0.045 Uiso 1 1 calc R U . . .
H00J H 0.8637 1.4351 0.3572 0.045 Uiso 1 1 calc R U . . .
N00K N 1.3197(2) 0.7834(2) 0.39846(17) 0.0435(6) Uani 1 1 d . . . . .
H00A H 1.3161 0.7324 0.4575 0.052 Uiso 1 1 calc R U . . .
H00B H 1.3873 0.8194 0.3757 0.052 Uiso 1 1 calc R U . . .
N00L N 0.9152(2) 0.7176(2) 0.36099(16) 0.0433(6) Uani 1 1 d . . . . .
H00C H 0.9101 0.6708 0.4218 0.052 Uiso 1 1 calc R U . . .
H00D H 0.8517 0.7307 0.3245 0.052 Uiso 1 1 calc R U . . .
C00M C 1.6164(3) 0.8157(2) 0.13060(18) 0.0340(6) Uani 1 1 d . . . . .
C00N C 1.5523(3) 0.7185(2) 0.18556(17) 0.0334(6) Uani 1 1 d . . . . .
C00O C 1.7241(3) 0.8563(2) 0.16656(19) 0.0367(6) Uani 1 1 d . . . . .
C00P C 1.2302(3) 1.4911(2) 0.40544(18) 0.0343(6) Uani 1 1 d . . . . .
C00Q C 1.0202(3) 0.7694(2) 0.32367(18) 0.0358(6) Uani 1 1 d . . . . .
C00R C 1.2275(3) 0.8920(2) 0.24396(18) 0.0353(6) Uani 1 1 d . . . . .
C00S C 1.0317(3) 1.4699(2) 0.36667(18) 0.0352(6) Uani 1 1 d . . . . .
C00T C 1.3471(3) 1.0409(2) 0.26472(18) 0.0354(6) Uani 1 1 d . . . . .
C00U C 1.2212(3) 0.8065(2) 0.34256(19) 0.0351(6) Uani 1 1 d . . . . .
C00V C 1.5935(3) 0.6361(2) 0.28583(18) 0.0346(6) Uani 1 1 d . . . . .
C00W C 1.1765(3) 1.5714(2) 0.23831(18) 0.0377(6) Uani 1 1 d . . . . .
H00W H 1.1996 1.6130 0.1718 0.045 Uiso 1 1 calc R U . . .
C00X C 1.4661(3) 1.0675(2) 0.27810(19) 0.0385(6) Uani 1 1 d . . . . .
H00X H 1.5390 1.0379 0.2536 0.046 Uiso 1 1 calc R U . . .
C00Y C 1.1268(3) 0.9039(2) 0.18961(19) 0.0375(6) Uani 1 1 d . . . . .
H00Y H 1.1281 0.9556 0.1242 0.045 Uiso 1 1 calc R U . . .
C00Z C 1.0576(3) 1.5380(2) 0.26304(18) 0.0356(6) Uani 1 1 d . . . . .
C010 C 0.9581(3) 1.5688(2) 0.18855(19) 0.0383(6) Uani 1 1 d . . . . .
H01L H 0.9855 1.6314 0.1298 0.046 Uiso 1 1 calc R U . . .
H01M H 0.8804 1.5937 0.2171 0.046 Uiso 1 1 calc R U . . .
C011 C 0.9292(3) 1.4757(2) 0.15620(18) 0.0375(6) Uani 1 1 d . . . . .
C012 C 1.0277(3) 1.4131(2) 0.12845(18) 0.0391(6) Uani 1 1 d . . . . .
H012 H 1.1110 1.4236 0.1363 0.047 Uiso 1 1 calc R U . . .
C013 C 1.2384(3) 1.0843(2) 0.3025(2) 0.0394(6) Uani 1 1 d . . . . .
H013 H 1.1589 1.0660 0.2934 0.047 Uiso 1 1 calc R U . . .
C014 C 0.7796(3) 1.3787(2) 0.1081(2) 0.0396(6) Uani 1 1 d . . . . .
C015 C 0.8046(3) 1.4570(2) 0.14751(19) 0.0391(6) Uani 1 1 d . . . . .
H015 H 0.7378 1.4968 0.1681 0.047 Uiso 1 1 calc R U . . .
C016 C 1.4798(3) 0.8564(2) 0.00673(19) 0.0394(7) Uani 1 1 d . . . . .
H016 H 1.4519 0.9026 -0.0554 0.047 Uiso 1 1 calc R U . . .
C017 C 0.8788(3) 1.3177(2) 0.07747(19) 0.0399(7) Uani 1 1 d . . . . .
C018 C 1.3367(3) 0.9660(2) 0.20657(19) 0.0382(6) Uani 1 1 d . . . . .
H01A H 1.3274 1.0125 0.1368 0.046 Uiso 1 1 calc R U . . .
H01B H 1.4149 0.9196 0.2105 0.046 Uiso 1 1 calc R U . . .
C019 C 1.0035(3) 1.3350(2) 0.08921(19) 0.0395(6) Uani 1 1 d . . . . .
C01A C 1.4755(3) 1.1394(2) 0.3289(2) 0.0395(6) Uani 1 1 d . . . . .
C01B C 1.2477(3) 1.1549(2) 0.3539(2) 0.0408(7) Uani 1 1 d . . . . .
C01C C 1.3674(3) 1.1828(2) 0.3669(2) 0.0405(7) Uani 1 1 d . . . . .
C01D C 1.4172(3) 0.7619(2) 0.06073(19) 0.0415(7) Uani 1 1 d . . . . .
H01W H 1.3486 0.7456 0.0341 0.050 Uiso 1 1 calc R U . . .
C01E C 1.2250(3) 1.2909(3) 0.0625(2) 0.0512(8) Uani 1 1 d . . . . .
H01N H 1.2412 1.3674 0.0230 0.077 Uiso 1 1 calc R U . . .
H01O H 1.2792 1.2425 0.0373 0.077 Uiso 1 1 calc R U . . .
H01P H 1.2415 1.2747 0.1308 0.077 Uiso 1 1 calc R U . . .
C01F C 1.3729(3) 1.1973(3) 0.5225(2) 0.0522(8) Uani 1 1 d . . . . .
H01C H 1.4348 1.1351 0.5406 0.078 Uiso 1 1 calc R U . . .
H01D H 1.2896 1.1706 0.5450 0.078 Uiso 1 1 calc R U . . .
H01E H 1.3896 1.2482 0.5533 0.078 Uiso 1 1 calc R U . . .
C01G C 1.0245(3) 1.1692(3) 0.3878(3) 0.0547(8) Uani 1 1 d . . . . .
H01F H 1.0052 1.1975 0.3188 0.082 Uiso 1 1 calc R U . . .
H01G H 0.9630 1.2005 0.4245 0.082 Uiso 1 1 calc R U . . .
H01H H 1.0223 1.0892 0.4147 0.082 Uiso 1 1 calc R U . . .
C01H C 0.5561(3) 1.4122(3) 0.1290(2) 0.0518(8) Uani 1 1 d . . . . .
H01Q H 0.5574 1.4913 0.0922 0.078 Uiso 1 1 calc R U . . .
H01R H 0.5615 1.3968 0.1988 0.078 Uiso 1 1 calc R U . . .
H01S H 0.4785 1.3860 0.1192 0.078 Uiso 1 1 calc R U . . .
C01I C 1.7023(3) 1.1269(3) 0.3088(3) 0.0606(9) Uani 1 1 d . . . . .
H01I H 1.7002 1.1490 0.2378 0.091 Uiso 1 1 calc R U . . .
H01J H 1.7093 1.0468 0.3394 0.091 Uiso 1 1 calc R U . . .
H01K H 1.7740 1.1569 0.3235 0.091 Uiso 1 1 calc R U . . .
C01J C 0.8991(4) 1.1342(3) 0.0700(3) 0.0589(9) Uani 1 1 d . . . . .
H01T H 0.9798 1.1274 0.0361 0.088 Uiso 1 1 calc R U . . .
H01U H 0.8411 1.0875 0.0595 0.088 Uiso 1 1 calc R U . . .
H01V H 0.9093 1.1113 0.1403 0.088 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00V 1.239(3) . ?
O002 C00V 1.262(3) . ?
O003 C00O 1.262(3) . ?
O004 H00K 0.8498 . ?
O004 H00L 0.8501 . ?
O005 C01C 1.376(3) . ?
O005 C01F 1.438(3) . ?
O006 C019 1.362(4) . ?
O006 C01E 1.433(4) . ?
O007 C017 1.371(3) . ?
O007 C01J 1.436(4) . ?
O008 C014 1.367(4) . ?
O008 C01H 1.413(4) . ?
O009 C00O 1.242(3) . ?
O00A C01B 1.360(4) . ?
O00A C01G 1.420(4) . ?
O00B C01A 1.362(3) . ?
O00B C01I 1.433(4) . ?
N00C C00P 1.331(3) . ?
N00C C00S 1.342(3) . ?
N00D C00Q 1.335(3) . ?
N00D C00U 1.339(3) . ?
N00E H00E 0.8600 . ?
N00E C00P 1.356(3) . ?
N00E C00W 1.360(3) . ?
N00F H00F 0.8600 . ?
N00F C00Q 1.359(3) . ?
N00F C00Y 1.356(4) . ?
N00G C00M 1.347(3) . ?
N00G C016 1.336(4) . ?
N00H C00N 1.335(3) . ?
N00H C01D 1.341(3) . ?
N00I H00G 0.8600 . ?
N00I H00H 0.8600 . ?
N00I C00P 1.326(3) . ?
N00J H00I 0.8600 . ?
N00J H00J 0.8600 . ?
N00J C00S 1.326(4) . ?
N00K H00A 0.8600 . ?
N00K H00B 0.8600 . ?
N00K C00U 1.325(3) . ?
N00L H00C 0.8600 . ?
N00L H00D 0.8600 . ?
N00L C00Q 1.316(4) . ?
C00M C00N 1.406(4) . ?
C00M C00O 1.509(4) . ?
C00N C00V 1.516(3) . ?
C00R C00U 1.438(4) . ?
C00R C00Y 1.349(4) . ?
C00R C018 1.498(4) . ?
C00S C00Z 1.440(4) . ?
C00T C00X 1.388(4) . ?
C00T C013 1.391(4) . ?
C00T C018 1.521(4) . ?
C00W H00W 0.9300 . ?
C00W C00Z 1.343(4) . ?
C00X H00X 0.9300 . ?
C00X C01A 1.401(4) . ?
C00Y H00Y 0.9300 . ?
C00Z C010 1.499(4) . ?
C010 H01L 0.9700 . ?
C010 H01M 0.9700 . ?
C010 C011 1.511(4) . ?
C011 C012 1.385(4) . ?
C011 C015 1.390(4) . ?
C012 H012 0.9300 . ?
C012 C019 1.384(4) . ?
C013 H013 0.9300 . ?
C013 C01B 1.393(4) . ?
C014 C015 1.390(4) . ?
C014 C017 1.397(4) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C01D 1.370(4) . ?
C017 C019 1.397(4) . ?
C018 H01A 0.9700 . ?
C018 H01B 0.9700 . ?
C01A C01C 1.388(4) . ?
C01B C01C 1.399(4) . ?
C01D H01W 0.9300 . ?
C01E H01N 0.9600 . ?
C01E H01O 0.9600 . ?
C01E H01P 0.9600 . ?
C01F H01C 0.9600 . ?
C01F H01D 0.9600 . ?
C01F H01E 0.9600 . ?
C01G H01F 0.9600 . ?
C01G H01G 0.9600 . ?
C01G H01H 0.9600 . ?
C01H H01Q 0.9600 . ?
C01H H01R 0.9600 . ?
C01H H01S 0.9600 . ?
C01I H01I 0.9600 . ?
C01I H01J 0.9600 . ?
C01I H01K 0.9600 . ?
C01J H01T 0.9600 . ?
C01J H01U 0.9600 . ?
C01J H01V 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H00K O004 H00L 109.5 . . ?
C01C O005 C01F 112.2(2) . . ?
C019 O006 C01E 118.0(2) . . ?
C017 O007 C01J 117.9(2) . . ?
C014 O008 C01H 117.8(2) . . ?
C01B O00A C01G 117.4(2) . . ?
C01A O00B C01I 117.7(2) . . ?
C00P N00C C00S 118.4(2) . . ?
C00Q N00D C00U 117.8(2) . . ?
C00P N00E H00E 120.2 . . ?
C00P N00E C00W 119.6(2) . . ?
C00W N00E H00E 120.2 . . ?
C00Q N00F H00F 120.5 . . ?
C00Y N00F H00F 120.5 . . ?
C00Y N00F C00Q 119.0(2) . . ?
C016 N00G C00M 116.9(2) . . ?
C00N N00H C01D 117.0(2) . . ?
H00G N00I H00H 120.0 . . ?
C00P N00I H00G 120.0 . . ?
C00P N00I H00H 120.0 . . ?
H00I N00J H00J 120.0 . . ?
C00S N00J H00I 120.0 . . ?
C00S N00J H00J 120.0 . . ?
H00A N00K H00B 120.0 . . ?
C00U N00K H00A 120.0 . . ?
C00U N00K H00B 120.0 . . ?
H00C N00L H00D 120.0 . . ?
C00Q N00L H00C 120.0 . . ?
C00Q N00L H00D 120.0 . . ?
N00G C00M C00N 120.6(2) . . ?
N00G C00M C00O 114.1(2) . . ?
C00N C00M C00O 125.2(2) . . ?
N00H C00N C00M 121.5(2) . . ?
N00H C00N C00V 116.0(2) . . ?
C00M C00N C00V 122.5(2) . . ?
O003 C00O C00M 115.8(2) . . ?
O009 C00O O003 127.2(3) . . ?
O009 C00O C00M 117.0(3) . . ?
N00C C00P N00E 121.9(2) . . ?
N00I C00P N00C 120.2(2) . . ?
N00I C00P N00E 117.9(2) . . ?
N00D C00Q N00F 122.8(2) . . ?
N00L C00Q N00D 119.4(2) . . ?
N00L C00Q N00F 117.9(2) . . ?
C00U C00R C018 121.7(2) . . ?
C00Y C00R C00U 115.7(2) . . ?
C00Y C00R C018 122.6(2) . . ?
N00C C00S C00Z 122.2(2) . . ?
N00J C00S N00C 116.8(2) . . ?
N00J C00S C00Z 120.9(2) . . ?
C00X C00T C013 120.2(3) . . ?
C00X C00T C018 119.3(3) . . ?
C013 C00T C018 120.5(3) . . ?
N00D C00U C00R 122.4(2) . . ?
N00K C00U N00D 117.8(2) . . ?
N00K C00U C00R 119.8(3) . . ?
O001 C00V O002 125.0(2) . . ?
O001 C00V C00N 118.5(2) . . ?
O002 C00V C00N 116.4(2) . . ?
N00E C00W H00W 119.0 . . ?
C00Z C00W N00E 122.1(2) . . ?
C00Z C00W H00W 119.0 . . ?
C00T C00X H00X 120.4 . . ?
C00T C00X C01A 119.3(3) . . ?
C01A C00X H00X 120.4 . . ?
N00F C00Y H00Y 119.0 . . ?
C00R C00Y N00F 122.1(2) . . ?
C00R C00Y H00Y 119.0 . . ?
C00S C00Z C010 121.9(2) . . ?
C00W C00Z C00S 115.3(2) . . ?
C00W C00Z C010 122.8(2) . . ?
C00Z C010 H01L 108.5 . . ?
C00Z C010 H01M 108.5 . . ?
C00Z C010 C011 114.9(2) . . ?
H01L C010 H01M 107.5 . . ?
C011 C010 H01L 108.5 . . ?
C011 C010 H01M 108.5 . . ?
C012 C011 C010 119.8(3) . . ?
C012 C011 C015 119.3(3) . . ?
C015 C011 C010 120.7(3) . . ?
C011 C012 H012 119.6 . . ?
C019 C012 C011 120.8(3) . . ?
C019 C012 H012 119.6 . . ?
C00T C013 H013 119.7 . . ?
C00T C013 C01B 120.5(3) . . ?
C01B C013 H013 119.7 . . ?
O008 C014 C015 124.1(3) . . ?
O008 C014 C017 115.4(3) . . ?
C015 C014 C017 120.6(3) . . ?
C011 C015 C014 120.2(3) . . ?
C011 C015 H015 119.9 . . ?
C014 C015 H015 119.9 . . ?
N00G C016 H016 118.8 . . ?
N00G C016 C01D 122.3(2) . . ?
C01D C016 H016 118.8 . . ?
O007 C017 C014 118.3(3) . . ?
O007 C017 C019 122.9(3) . . ?
C014 C017 C019 118.7(3) . . ?
C00R C018 C00T 113.4(2) . . ?
C00R C018 H01A 108.9 . . ?
C00R C018 H01B 108.9 . . ?
C00T C018 H01A 108.9 . . ?
C00T C018 H01B 108.9 . . ?
H01A C018 H01B 107.7 . . ?
O006 C019 C012 124.3(3) . . ?
O006 C019 C017 115.3(2) . . ?
C012 C019 C017 120.4(3) . . ?
O00B C01A C00X 123.6(3) . . ?
O00B C01A C01C 115.6(2) . . ?
C01C C01A C00X 120.8(3) . . ?
O00A C01B C013 124.8(3) . . ?
O00A C01B C01C 115.6(3) . . ?
C013 C01B C01C 119.6(3) . . ?
O005 C01C C01A 119.3(3) . . ?
O005 C01C C01B 121.1(3) . . ?
C01A C01C C01B 119.6(3) . . ?
N00H C01D C016 121.6(3) . . ?
N00H C01D H01W 119.2 . . ?
C016 C01D H01W 119.2 . . ?
O006 C01E H01N 109.5 . . ?
O006 C01E H01O 109.5 . . ?
O006 C01E H01P 109.5 . . ?
H01N C01E H01O 109.5 . . ?
H01N C01E H01P 109.5 . . ?
H01O C01E H01P 109.5 . . ?
O005 C01F H01C 109.5 . . ?
O005 C01F H01D 109.5 . . ?
O005 C01F H01E 109.5 . . ?
H01C C01F H01D 109.5 . . ?
H01C C01F H01E 109.5 . . ?
H01D C01F H01E 109.5 . . ?
O00A C01G H01F 109.5 . . ?
O00A C01G H01G 109.5 . . ?
O00A C01G H01H 109.5 . . ?
H01F C01G H01G 109.5 . . ?
H01F C01G H01H 109.5 . . ?
H01G C01G H01H 109.5 . . ?
O008 C01H H01Q 109.5 . . ?
O008 C01H H01R 109.5 . . ?
O008 C01H H01S 109.5 . . ?
H01Q C01H H01R 109.5 . . ?
H01Q C01H H01S 109.5 . . ?
H01R C01H H01S 109.5 . . ?
O00B C01I H01I 109.5 . . ?
O00B C01I H01J 109.5 . . ?
O00B C01I H01K 109.5 . . ?
H01I C01I H01J 109.5 . . ?
H01I C01I H01K 109.5 . . ?
H01J C01I H01K 109.5 . . ?
O007 C01J H01T 109.5 . . ?
O007 C01J H01U 109.5 . . ?
O007 C01J H01V 109.5 . . ?
H01T C01J H01U 109.5 . . ?
H01T C01J H01V 109.5 . . ?
H01U C01J H01V 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O007 C017 C019 O006 -3.8(4) . . . . ?
O007 C017 C019 C012 174.4(2) . . . . ?
O008 C014 C015 C011 -178.4(2) . . . . ?
O008 C014 C017 O007 4.3(4) . . . . ?
O008 C014 C017 C019 -179.7(2) . . . . ?
O00A C01B C01C O005 -2.2(4) . . . . ?
O00A C01B C01C C01A 178.7(2) . . . . ?
O00B C01A C01C O005 2.5(4) . . . . ?
O00B C01A C01C C01B -178.4(2) . . . . ?
N00C C00S C00Z C00W 6.8(4) . . . . ?
N00C C00S C00Z C010 -173.4(3) . . . . ?
N00E C00W C00Z C00S -2.7(4) . . . . ?
N00E C00W C00Z C010 177.5(3) . . . . ?
N00G C00M C00N N00H -1.0(4) . . . . ?
N00G C00M C00N C00V 177.6(2) . . . . ?
N00G C00M C00O O003 -76.2(3) . . . . ?
N00G C00M C00O O009 100.9(3) . . . . ?
N00G C016 C01D N00H 0.4(5) . . . . ?
N00H C00N C00V O001 167.5(3) . . . . ?
N00H C00N C00V O002 -10.4(4) . . . . ?
N00J C00S C00Z C00W -175.0(3) . . . . ?
N00J C00S C00Z C010 4.8(4) . . . . ?
C00M N00G C016 C01D -0.3(4) . . . . ?
C00M C00N C00V O001 -11.1(4) . . . . ?
C00M C00N C00V O002 171.0(3) . . . . ?
C00N N00H C01D C016 -0.7(4) . . . . ?
C00N C00M C00O O003 107.1(3) . . . . ?
C00N C00M C00O O009 -75.9(4) . . . . ?
C00O C00M C00N N00H 175.6(3) . . . . ?
C00O C00M C00N C00V -5.9(4) . . . . ?
C00P N00C C00S N00J 177.5(2) . . . . ?
C00P N00C C00S C00Z -4.2(4) . . . . ?
C00P N00E C00W C00Z -3.6(4) . . . . ?
C00Q N00D C00U N00K -178.1(3) . . . . ?
C00Q N00D C00U C00R 2.0(4) . . . . ?
C00Q N00F C00Y C00R 1.8(4) . . . . ?
C00S N00C C00P N00E -2.7(4) . . . . ?
C00S N00C C00P N00I 176.2(3) . . . . ?
C00S C00Z C010 C011 -75.3(3) . . . . ?
C00T C00X C01A O00B 178.8(2) . . . . ?
C00T C00X C01A C01C 0.9(4) . . . . ?
C00T C013 C01B O00A -178.5(2) . . . . ?
C00T C013 C01B C01C 0.5(4) . . . . ?
C00U N00D C00Q N00F 3.2(4) . . . . ?
C00U N00D C00Q N00L -176.7(3) . . . . ?
C00U C00R C00Y N00F 3.0(4) . . . . ?
C00U C00R C018 C00T -64.2(3) . . . . ?
C00W N00E C00P N00C 6.6(4) . . . . ?
C00W N00E C00P N00I -172.2(2) . . . . ?
C00W C00Z C010 C011 104.5(3) . . . . ?
C00X C00T C013 C01B 0.1(4) . . . . ?
C00X C00T C018 C00R 146.4(2) . . . . ?
C00X C01A C01C O005 -179.4(2) . . . . ?
C00X C01A C01C C01B -0.3(4) . . . . ?
C00Y N00F C00Q N00D -5.2(4) . . . . ?
C00Y N00F C00Q N00L 174.7(3) . . . . ?
C00Y C00R C00U N00D -5.0(4) . . . . ?
C00Y C00R C00U N00K 175.1(3) . . . . ?
C00Y C00R C018 C00T 112.9(3) . . . . ?
C00Z C010 C011 C012 -47.5(3) . . . . ?
C00Z C010 C011 C015 136.9(3) . . . . ?
C010 C011 C012 C019 -173.5(2) . . . . ?
C010 C011 C015 C014 173.5(2) . . . . ?
C011 C012 C019 O006 177.7(2) . . . . ?
C011 C012 C019 C017 -0.4(4) . . . . ?
C012 C011 C015 C014 -2.2(4) . . . . ?
C013 C00T C00X C01A -0.8(4) . . . . ?
C013 C00T C018 C00R -34.8(3) . . . . ?
C013 C01B C01C O005 178.7(2) . . . . ?
C013 C01B C01C C01A -0.4(4) . . . . ?
C014 C017 C019 O006 -179.6(2) . . . . ?
C014 C017 C019 C012 -1.4(4) . . . . ?
C015 C011 C012 C019 2.2(4) . . . . ?
C015 C014 C017 O007 -174.6(2) . . . . ?
C015 C014 C017 C019 1.4(4) . . . . ?
C016 N00G C00M C00N 0.6(4) . . . . ?
C016 N00G C00M C00O -176.3(2) . . . . ?
C017 C014 C015 C011 0.4(4) . . . . ?
C018 C00R C00U N00D 172.3(3) . . . . ?
C018 C00R C00U N00K -7.6(4) . . . . ?
C018 C00R C00Y N00F -174.4(3) . . . . ?
C018 C00T C00X C01A 178.0(2) . . . . ?
C018 C00T C013 C01B -178.6(2) . . . . ?
C01D N00H C00N C00M 1.0(4) . . . . ?
C01D N00H C00N C00V -177.6(2) . . . . ?
C01E O006 C019 C012 -1.2(4) . . . . ?
C01E O006 C019 C017 177.0(2) . . . . ?
C01F O005 C01C C01A -98.3(3) . . . . ?
C01F O005 C01C C01B 82.6(3) . . . . ?
C01G O00A C01B C013 1.6(4) . . . . ?
C01G O00A C01B C01C -177.4(3) . . . . ?
C01H O008 C014 C015 -4.3(4) . . . . ?
C01H O008 C014 C017 176.9(2) . . . . ?
C01I O00B C01A C00X 2.6(4) . . . . ?
C01I O00B C01A C01C -179.5(3) . . . . ?
C01J O007 C017 C014 -127.9(3) . . . . ?
C01J O007 C017 C019 56.3(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 2.003
_oxdiff_exptl_absorpt_empirical_full_min 0.469
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_r20230530d_autored
_database_code_depnum_ccdc_archive 'CCDC 2283935'
loop_
_audit_author_name
_audit_author_address
'Zhang liang'
;Tianjin University
China
;
_audit_update_record             
;
2023-07-24 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H3 N2 O4, C14.37 H20.49 N4 O3.37'
_chemical_formula_sum            'C20.37 H23.49 N6 O7.37'
_chemical_formula_weight         470.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.4664(4)
_cell_length_b                   12.6295(2)
_cell_length_c                   12.7478(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.155(3)
_cell_angle_gamma                90
_cell_volume                     2172.10(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18514
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.6680
_cell_measurement_theta_min      2.1940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             987
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30763
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_min         2.209
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_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   -110.00  70.00   0.50   12.00    --  -20.00   0.00   0.00  360
  2  ω   -110.00   5.00   0.50   12.00    --  -20.00 -70.00  90.00  230
  3  ω   -110.00 -21.00   0.50   12.00    --  -20.00 -70.00   0.00  178
  4  ω    -90.00   7.00   0.50   12.00    --  -20.00 -70.00 180.00  194
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 944'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0447977000
_diffrn_orient_matrix_UB_12      0.0287641000
_diffrn_orient_matrix_UB_13      0.0124242000
_diffrn_orient_matrix_UB_21      0.0272121000
_diffrn_orient_matrix_UB_22      -0.0480111000
_diffrn_orient_matrix_UB_23      0.0123413000
_diffrn_orient_matrix_UB_31      -0.0042390000
_diffrn_orient_matrix_UB_32      -0.0041040000
_diffrn_orient_matrix_UB_33      -0.0570782000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5064
_reflns_number_total             6083
_reflns_odcompleteness_completeness 93.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     34.72
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6083
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.025
_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)+(0.0727P)²+0.7274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1395
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O1-C12 \\sim O1A-C12A \\sim O2-C13 \\sim O2A-C13A \\sim O3-C14 \\sim O3A-C14A
 with sigma of 0.01
 C5-C6 \\sim C5-C6A
 with sigma of 0.01
 C8-O1 \\sim C8A-O1A \\sim C9-O2 \\sim C9A-O2A \\sim C10-O3 \\sim C10A-O3A
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6A)
Uanis(C7) = Uanis(C7A)
Uanis(C11) = Uanis(C11A)
3. Others
 Sof(H5BD)=Sof(H5BC)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=
 Sof(C8A)=Sof(C9A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12D)=Sof(H12E)=
 Sof(H12F)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C14A)=Sof(H14D)=
 Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(H5AB)=Sof(H5AA)=Sof(O1)=Sof(O2)=Sof(O3)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=
 Sof(C9)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 FVAR(1)
 Sof(O8)=Sof(H8)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C5(H5AB,H5AA), C5(H5BD,H5BC)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C2(H2A), C7(H7), C11(H11), C7A(H7A), C11A(H11A)
4.c Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C10,C11), C6A(C7A,C8A,C9A,C10A,C11A)
4.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12A(H12D,H12E,
 H12F), C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F), C21(H21A,H21B,H21C)
4.e Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_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
O4 O 0.11592(8) 0.64877(7) 0.30165(8) 0.0228(2) Uani 1 1 d . . . . .
O5 O 0.08642(9) 0.73381(8) 0.43938(9) 0.0314(3) Uani 1 1 d . . . . .
O6 O 0.23396(7) 0.70659(7) 0.67148(8) 0.0251(2) Uani 1 1 d . . . . .
O7 O 0.08679(7) 0.67766(7) 0.68865(8) 0.0220(2) Uani 1 1 d . . . . .
H7B H 0.1040(16) 0.7383(19) 0.732(2) 0.053(6) Uiso 1 1 d . . . . .
N5 N 0.12233(8) 0.46190(8) 0.41361(9) 0.0186(2) Uani 1 1 d . . . . .
N6 N 0.14544(8) 0.46744(8) 0.64048(9) 0.0183(2) Uani 1 1 d . . . . .
C15 C 0.12633(8) 0.55402(9) 0.46713(10) 0.0141(2) Uani 1 1 d . . . . .
C16 C 0.13992(8) 0.55652(9) 0.58120(10) 0.0146(2) Uani 1 1 d . . . . .
C17 C 0.14011(10) 0.37617(10) 0.58558(11) 0.0208(3) Uani 1 1 d . . . . .
H17 H 0.143082 0.311356 0.624475 0.025 Uiso 1 1 calc R . . . .
C18 C 0.13038(10) 0.37357(10) 0.47355(11) 0.0216(3) Uani 1 1 d . . . . .
H18 H 0.129413 0.307032 0.438401 0.026 Uiso 1 1 calc R . . . .
C19 C 0.10886(9) 0.65460(9) 0.39808(10) 0.0154(2) Uani 1 1 d . . . . .
C20 C 0.15762(9) 0.65742(9) 0.64972(10) 0.0166(2) Uani 1 1 d . . . . .
N1 N 0.04374(9) 0.39852(9) 0.16910(10) 0.0215(2) Uani 1 1 d . . . . .
H1A H -0.0011(14) 0.3503(15) 0.1397(16) 0.032(5) Uiso 1 1 d . . . . .
H1B H 0.0546(14) 0.4245(15) 0.2335(17) 0.034(5) Uiso 1 1 d . . . . .
N2 N 0.15686(8) 0.51832(8) 0.14931(9) 0.0183(2) Uani 1 1 d . . . . .
H2 H 0.1547(14) 0.5523(15) 0.2094(17) 0.034(5) Uiso 1 1 d . . . . .
N3 N 0.07918(8) 0.39437(8) 0.00725(9) 0.0169(2) Uani 1 1 d . . . . .
N4 N 0.11160(9) 0.39359(9) -0.15459(9) 0.0194(2) Uani 1 1 d . . . . .
H4A H 0.0531(13) 0.3604(14) -0.1843(14) 0.025(4) Uiso 1 1 d . . . . .
H4B H 0.1339(14) 0.4270(15) -0.2028(16) 0.031(5) Uiso 1 1 d . . . . .
C1 C 0.09329(9) 0.43646(9) 0.10765(10) 0.0161(2) Uani 1 1 d . . . . .
C2 C 0.21531(9) 0.55356(9) 0.09290(10) 0.0181(2) Uani 1 1 d . . . . .
H2A H 0.260564 0.609882 0.123514 0.022 Uiso 1 1 calc R . . . .
C3 C 0.20961(9) 0.50943(9) -0.00573(10) 0.0175(2) Uani 1 1 d . . . . .
C4 C 0.13261(9) 0.43238(9) -0.05064(10) 0.0155(2) Uani 1 1 d . . . . .
C5 C 0.27487(11) 0.54026(11) -0.07014(12) 0.0253(3) Uani 1 1 d D . . . .
H5AB H 0.233394 0.575696 -0.140718 0.030 Uiso 0.632(5) 1 calc R . P A 1
H5AA H 0.302010 0.474976 -0.091019 0.030 Uiso 0.632(5) 1 calc R . P A 1
H5BD H 0.295003 0.475639 -0.100355 0.030 Uiso 0.368(5) 1 calc R . P A 2
H5BC H 0.236607 0.585475 -0.134645 0.030 Uiso 0.368(5) 1 calc R . P A 2
O1 O 0.5972(4) 0.6060(4) 0.2378(5) 0.0531(13) Uani 0.632(5) 1 d D . P A 1
O2 O 0.6038(3) 0.8023(3) 0.1681(3) 0.0419(8) Uani 0.632(5) 1 d D . P A 1
O3 O 0.4606(3) 0.8801(3) -0.0133(3) 0.0355(7) Uani 0.632(5) 1 d D . P A 1
C6 C 0.3608(4) 0.6131(4) -0.0071(5) 0.0222(6) Uani 0.632(5) 1 d D . P A 1
C7 C 0.4373(4) 0.5714(3) 0.0845(5) 0.0279(5) Uani 0.632(5) 1 d G . P A 1
H7 H 0.433219 0.500684 0.107907 0.033 Uiso 0.632(5) 1 calc R . P A 1
C8 C 0.5197(3) 0.6330(3) 0.1417(3) 0.0285(8) Uani 0.632(5) 1 d DG . P A 1
C9 C 0.5256(2) 0.7365(3) 0.1074(3) 0.0299(8) Uani 0.632(5) 1 d DG . P A 1
C10 C 0.4491(3) 0.7782(2) 0.0158(3) 0.0260(8) Uani 0.632(5) 1 d DG . P A 1
C11 C 0.3667(3) 0.7166(4) -0.0414(3) 0.0252(6) Uani 0.632(5) 1 d G . P A 1
H11 H 0.314457 0.745131 -0.103939 0.030 Uiso 0.632(5) 1 calc R . P A 1
C12 C 0.5933(5) 0.5026(5) 0.2809(7) 0.0478(15) Uani 0.632(5) 1 d D . P A 1
H12A H 0.600947 0.449524 0.228527 0.072 Uiso 0.632(5) 1 calc GR . P A 1
H12B H 0.529305 0.492531 0.289714 0.072 Uiso 0.632(5) 1 calc GR . P A 1
H12C H 0.646910 0.494601 0.354118 0.072 Uiso 0.632(5) 1 calc GR . P A 1
C13 C 0.6825(2) 0.8023(3) 0.1263(4) 0.0617(12) Uani 0.632(5) 1 d D . P A 1
H13A H 0.735287 0.849642 0.172184 0.093 Uiso 0.632(5) 1 calc GR . P A 1
H13B H 0.657764 0.826899 0.048128 0.093 Uiso 0.632(5) 1 calc GR . P A 1
H13C H 0.708779 0.730315 0.129755 0.093 Uiso 0.632(5) 1 calc GR . P A 1
C14 C 0.3849(7) 0.9219(8) -0.1108(6) 0.0487(17) Uani 0.632(5) 1 d D . P A 1
H14A H 0.381600 0.880076 -0.176842 0.073 Uiso 0.632(5) 1 calc GR . P A 1
H14B H 0.400317 0.995667 -0.121713 0.073 Uiso 0.632(5) 1 calc GR . P A 1
H14C H 0.320962 0.918499 -0.100719 0.073 Uiso 0.632(5) 1 calc GR . P A 1
O1A O 0.5942(6) 0.5731(6) 0.2450(6) 0.0393(18) Uani 0.368(5) 1 d D . P A 2
O2A O 0.5967(6) 0.7859(7) 0.2022(5) 0.059(2) Uani 0.368(5) 1 d D . P A 2
O3A O 0.4568(5) 0.8738(5) 0.0266(5) 0.0366(12) Uani 0.368(5) 1 d D . P A 2
C6A C 0.3651(7) 0.5983(7) 0.0014(9) 0.0222(6) Uani 0.368(5) 1 d D . P A 2
C7A C 0.4387(8) 0.5553(5) 0.0949(10) 0.0279(5) Uani 0.368(5) 1 d G . P A 2
H7A H 0.437024 0.482176 0.111696 0.033 Uiso 0.368(5) 1 calc R . P A 2
C8A C 0.5146(5) 0.6192(6) 0.1637(6) 0.0383(19) Uani 0.368(5) 1 d DG . P A 2
C9A C 0.5170(4) 0.7261(5) 0.1390(4) 0.0342(15) Uani 0.368(5) 1 d DG . P A 2
C10A C 0.4434(5) 0.7692(5) 0.0456(5) 0.0302(14) Uani 0.368(5) 1 d DG . P A 2
C11A C 0.3675(5) 0.7053(7) -0.0232(6) 0.0252(6) Uani 0.368(5) 1 d G . P A 2
H11A H 0.317200 0.734703 -0.087081 0.030 Uiso 0.368(5) 1 calc R . P A 2
C12A C 0.5870(10) 0.4647(7) 0.2723(10) 0.041(2) Uani 0.368(5) 1 d D . P A 2
H12D H 0.584965 0.420097 0.208538 0.062 Uiso 0.368(5) 1 calc GR . P A 2
H12E H 0.526402 0.453925 0.288454 0.062 Uiso 0.368(5) 1 calc GR . P A 2
H12F H 0.644746 0.445463 0.338498 0.062 Uiso 0.368(5) 1 calc GR . P A 2
C13A C 0.6113(5) 0.7926(5) 0.3164(4) 0.0577(18) Uani 0.368(5) 1 d D . P A 2
H13D H 0.547678 0.806000 0.325123 0.087 Uiso 0.368(5) 1 calc GR . P A 2
H13E H 0.657190 0.850633 0.350704 0.087 Uiso 0.368(5) 1 calc GR . P A 2
H13F H 0.639147 0.725829 0.353648 0.087 Uiso 0.368(5) 1 calc GR . P A 2
C14A C 0.3900(10) 0.9185(11) -0.0758(9) 0.045(3) Uani 0.368(5) 1 d D . P A 2
H14D H 0.393114 0.877651 -0.139799 0.067 Uiso 0.368(5) 1 calc GR . P A 2
H14E H 0.408884 0.992114 -0.082139 0.067 Uiso 0.368(5) 1 calc GR . P A 2
H14F H 0.322357 0.916472 -0.075650 0.067 Uiso 0.368(5) 1 calc GR . P A 2
O8 O 0.6947(3) 0.7940(3) 0.4002(3) 0.0440(11) Uani 0.372(4) 1 d . . P B 1
H8 H 0.673224 0.773327 0.333084 0.066 Uiso 0.372(4) 1 calc GR . P B 1
C21 C 0.6398(6) 0.7494(6) 0.4563(6) 0.067(2) Uani 0.372(4) 1 d . . P B 1
H21A H 0.672044 0.762513 0.537101 0.101 Uiso 0.372(4) 1 calc GR . P B 1
H21B H 0.634534 0.672902 0.442354 0.101 Uiso 0.372(4) 1 calc GR . P B 1
H21C H 0.573318 0.780739 0.429463 0.101 Uiso 0.372(4) 1 calc GR . 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
O4 C19 1.2718(15) . ?
O5 C19 1.2275(15) . ?
O6 C20 1.2087(15) . ?
O7 H7B 0.92(2) . ?
O7 C20 1.3148(15) . ?
N5 C15 1.3394(15) . ?
N5 C18 1.3333(16) . ?
N6 C16 1.3414(15) . ?
N6 C17 1.3362(16) . ?
C15 C16 1.3957(16) . ?
C15 C19 1.5137(16) . ?
C16 C20 1.5136(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3839(19) . ?
C18 H18 0.9500 . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.84(2) . ?
N1 C1 1.3276(16) . ?
N2 H2 0.89(2) . ?
N2 C1 1.3580(16) . ?
N2 C2 1.3671(17) . ?
N3 C1 1.3318(15) . ?
N3 C4 1.3358(15) . ?
N4 H4A 0.896(18) . ?
N4 H4B 0.90(2) . ?
N4 C4 1.3408(16) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3503(17) . ?
C3 C4 1.4335(16) . ?
C3 C5 1.5089(18) . ?
C5 H5AB 0.9900 . ?
C5 H5AA 0.9900 . ?
C5 H5BD 0.9900 . ?
C5 H5BC 0.9900 . ?
C5 C6 1.522(3) . ?
C5 C6A 1.488(4) . ?
O1 C8 1.372(4) . ?
O1 C12 1.426(5) . ?
O2 C9 1.392(3) . ?
O2 C13 1.420(4) . ?
O3 C10 1.365(3) . ?
O3 C14 1.428(5) . ?
C6 C7 1.3900 . ?
C6 C11 1.3900 . ?
C7 H7 0.9500 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1A C8A 1.370(6) . ?
O1A C12A 1.426(6) . ?
O2A C9A 1.370(6) . ?
O2A C13A 1.396(6) . ?
O3A C10A 1.370(5) . ?
O3A C14A 1.430(7) . ?
C6A C7A 1.3900 . ?
C6A C11A 1.3900 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.3900 . ?
C8A C9A 1.3900 . ?
C9A C10A 1.3900 . ?
C10A C11A 1.3900 . ?
C11A H11A 0.9500 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
O8 H8 0.8400 . ?
O8 C21 1.367(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C20 O7 H7B 107.8(14) . . ?
C18 N5 C15 117.14(11) . . ?
C17 N6 C16 116.61(10) . . ?
N5 C15 C16 120.95(10) . . ?
N5 C15 C19 117.73(10) . . ?
C16 C15 C19 121.20(10) . . ?
N6 C16 C15 121.69(10) . . ?
N6 C16 C20 114.69(10) . . ?
C15 C16 C20 123.45(10) . . ?
N6 C17 H17 119.1 . . ?
N6 C17 C18 121.75(11) . . ?
C18 C17 H17 119.1 . . ?
N5 C18 C17 121.79(11) . . ?
N5 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
O4 C19 C15 117.30(10) . . ?
O5 C19 O4 125.99(11) . . ?
O5 C19 C15 116.68(10) . . ?
O6 C20 O7 125.84(11) . . ?
O6 C20 C16 121.02(11) . . ?
O7 C20 C16 112.88(10) . . ?
H1A N1 H1B 122.7(18) . . ?
C1 N1 H1A 118.4(13) . . ?
C1 N1 H1B 118.8(13) . . ?
C1 N2 H2 118.3(12) . . ?
C1 N2 C2 120.14(11) . . ?
C2 N2 H2 121.2(12) . . ?
C1 N3 C4 117.96(11) . . ?
H4A N4 H4B 116.7(16) . . ?
C4 N4 H4A 115.5(11) . . ?
C4 N4 H4B 119.8(12) . . ?
N1 C1 N2 118.53(11) . . ?
N1 C1 N3 119.66(11) . . ?
N3 C1 N2 121.81(11) . . ?
N2 C2 H2A 119.5 . . ?
C3 C2 N2 120.92(11) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 C4 115.44(11) . . ?
C2 C3 C5 124.07(11) . . ?
C4 C3 C5 120.42(11) . . ?
N3 C4 N4 116.40(11) . . ?
N3 C4 C3 122.99(11) . . ?
N4 C4 C3 120.60(11) . . ?
C3 C5 H5AB 108.5 . . ?
C3 C5 H5AA 108.5 . . ?
C3 C5 H5BD 109.2 . . ?
C3 C5 H5BC 109.2 . . ?
C3 C5 C6 114.9(3) . . ?
H5AB C5 H5AA 107.5 . . ?
H5BD C5 H5BC 107.9 . . ?
C6 C5 H5AB 108.5 . . ?
C6 C5 H5AA 108.6 . . ?
C6A C5 C3 112.1(5) . . ?
C6A C5 H5BD 109.2 . . ?
C6A C5 H5BC 109.2 . . ?
C8 O1 C12 116.0(5) . . ?
C9 O2 C13 113.1(3) . . ?
C10 O3 C14 117.1(5) . . ?
C7 C6 C5 117.7(3) . . ?
C7 C6 C11 120.0 . . ?
C11 C6 C5 122.2(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
O1 C8 C7 126.8(3) . . ?
O1 C8 C9 113.1(3) . . ?
C7 C8 C9 120.0 . . ?
C8 C9 O2 121.1(3) . . ?
C10 C9 O2 118.8(3) . . ?
C10 C9 C8 120.0 . . ?
O3 C10 C9 116.6(3) . . ?
O3 C10 C11 123.4(3) . . ?
C9 C10 C11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C10 C11 C6 120.0 . . ?
C10 C11 H11 120.0 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8A O1A C12A 118.5(8) . . ?
C9A O2A C13A 115.2(5) . . ?
C10A O3A C14A 116.8(8) . . ?
C7A C6A C5 124.3(6) . . ?
C7A C6A C11A 120.0 . . ?
C11A C6A C5 115.4(6) . . ?
C6A C7A H7A 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
O1A C8A C7A 119.2(6) . . ?
O1A C8A C9A 120.1(6) . . ?
C9A C8A C7A 120.0 . . ?
O2A C9A C8A 119.1(6) . . ?
O2A C9A C10A 120.7(6) . . ?
C8A C9A C10A 120.0 . . ?
O3A C10A C9A 114.6(6) . . ?
O3A C10A C11A 125.3(6) . . ?
C11A C10A C9A 120.0 . . ?
C6A C11A H11A 120.0 . . ?
C10A C11A C6A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
O1A C12A H12D 109.5 . . ?
O1A C12A H12E 109.5 . . ?
O1A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
O2A C13A H13D 109.5 . . ?
O2A C13A H13E 109.5 . . ?
O2A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O3A C14A H14D 109.5 . . ?
O3A C14A H14E 109.5 . . ?
O3A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C21 O8 H8 109.5 . . ?
O8 C21 H21A 109.5 . . ?
O8 C21 H21B 109.5 . . ?
O8 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C15 C16 N6 -2.76(18) . . . . ?
N5 C15 C16 C20 172.23(11) . . . . ?
N5 C15 C19 O4 -16.99(16) . . . . ?
N5 C15 C19 O5 161.04(12) . . . . ?
N6 C16 C20 O6 106.61(13) . . . . ?
N6 C16 C20 O7 -67.83(14) . . . . ?
N6 C17 C18 N5 -2.4(2) . . . . ?
C15 N5 C18 C17 1.49(19) . . . . ?
C15 C16 C20 O6 -68.70(16) . . . . ?
C15 C16 C20 O7 116.86(13) . . . . ?
C16 N6 C17 C18 0.63(19) . . . . ?
C16 C15 C19 O4 166.96(11) . . . . ?
C16 C15 C19 O5 -15.00(17) . . . . ?
C17 N6 C16 C15 1.85(17) . . . . ?
C17 N6 C16 C20 -173.55(11) . . . . ?
C18 N5 C15 C16 0.98(17) . . . . ?
C18 N5 C15 C19 -175.08(11) . . . . ?
C19 C15 C16 N6 173.16(10) . . . . ?
C19 C15 C16 C20 -11.85(17) . . . . ?
N2 C2 C3 C4 5.91(17) . . . . ?
N2 C2 C3 C5 -176.95(12) . . . . ?
C1 N2 C2 C3 1.34(18) . . . . ?
C1 N3 C4 N4 -175.41(11) . . . . ?
C1 N3 C4 C3 5.41(17) . . . . ?
C2 N2 C1 N1 174.46(11) . . . . ?
C2 N2 C1 N3 -6.04(18) . . . . ?
C2 C3 C4 N3 -9.58(17) . . . . ?
C2 C3 C4 N4 171.27(11) . . . . ?
C2 C3 C5 C6 9.7(3) . . . . ?
C2 C3 C5 C6A 17.9(5) . . . . ?
C3 C5 C6 C7 69.2(4) . . . . ?
C3 C5 C6 C11 -113.9(4) . . . . ?
C3 C5 C6A C7A 63.4(7) . . . . ?
C3 C5 C6A C11A -109.8(6) . . . . ?
C4 N3 C1 N1 -177.95(11) . . . . ?
C4 N3 C1 N2 2.56(17) . . . . ?
C4 C3 C5 C6 -173.3(3) . . . . ?
C4 C3 C5 C6A -165.1(5) . . . . ?
C5 C3 C4 N3 173.17(12) . . . . ?
C5 C3 C4 N4 -5.98(18) . . . . ?
C5 C6 C7 C8 177.0(6) . . . . ?
C5 C6 C11 C10 -176.8(6) . . . . ?
C5 C6A C7A C8A -172.9(11) . . . . ?
C5 C6A C11A C10A 173.5(10) . . . . ?
O1 C8 C9 O2 -0.2(5) . . . . ?
O1 C8 C9 C10 -175.6(5) . . . . ?
O2 C9 C10 O3 5.0(4) . . . . ?
O2 C9 C10 C11 -175.4(4) . . . . ?
O3 C10 C11 C6 179.5(4) . . . . ?
C6 C7 C8 O1 174.9(5) . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C6 C11 C10 0.0 . . . . ?
C7 C8 C9 O2 175.3(4) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 O3 -179.6(3) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C6 0.0 . . . . ?
C11 C6 C7 C8 0.0 . . . . ?
C12 O1 C8 C7 1.8(8) . . . . ?
C12 O1 C8 C9 177.0(5) . . . . ?
C13 O2 C9 C8 94.7(4) . . . . ?
C13 O2 C9 C10 -89.9(4) . . . . ?
C14 O3 C10 C9 176.8(5) . . . . ?
C14 O3 C10 C11 -2.8(6) . . . . ?
O1A C8A C9A O2A -4.4(9) . . . . ?
O1A C8A C9A C10A 170.2(8) . . . . ?
O2A C9A C10A O3A -2.0(7) . . . . ?
O2A C9A C10A C11A 174.6(7) . . . . ?
O3A C10A C11A C6A 176.2(7) . . . . ?
C6A C7A C8A O1A -170.3(7) . . . . ?
C6A C7A C8A C9A 0.0 . . . . ?
C7A C6A C11A C10A 0.0 . . . . ?
C7A C8A C9A O2A -174.6(7) . . . . ?
C7A C8A C9A C10A 0.0 . . . . ?
C8A C9A C10A O3A -176.6(6) . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C9A C10A C11A C6A 0.0 . . . . ?
C11A C6A C7A C8A 0.0 . . . . ?
C12A O1A C8A C7A -13.0(10) . . . . ?
C12A O1A C8A C9A 176.7(7) . . . . ?
C13A O2A C9A C8A -61.5(10) . . . . ?
C13A O2A C9A C10A 123.9(7) . . . . ?
C14A O3A C10A C9A 172.6(8) . . . . ?
C14A O3A C10A C11A -3.8(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.850
_oxdiff_exptl_absorpt_empirical_full_min 0.397
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_r20230615c_autored
_database_code_depnum_ccdc_archive 'CCDC 2286188'
loop_
_audit_author_name
_audit_author_address
'zhang liang'
;Tianjin University
China
;
_audit_update_record             
;
2024-05-19 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H3 O5, C14 H19 N4 O3'
_chemical_formula_sum            'C20 H22 N4 O8'
_chemical_formula_weight         446.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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                   16.9699(4)
_cell_length_b                   17.1267(5)
_cell_length_c                   17.9029(3)
_cell_angle_alpha                63.782(3)
_cell_angle_beta                 64.481(2)
_cell_angle_gamma                84.746(2)
_cell_volume                     4181.1(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28644
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.7140
_cell_measurement_theta_min      1.9940
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17016
_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         26.373
_diffrn_reflns_theta_min         1.772
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    2.00    --  -20.00   0.00   0.00  360
  2  ω   -110.00  70.00   0.50    2.00    --  -20.00   0.00  90.00  360
  3  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00 180.00  234
  4  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00   0.00  234
  5  ω   -110.00   6.00   0.50    2.00    --  -20.00 -70.00  90.00  232
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku MM007 Saturn944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0370526000
_diffrn_orient_matrix_UB_12      0.0232167000
_diffrn_orient_matrix_UB_13      0.0015734000
_diffrn_orient_matrix_UB_21      0.0281487000
_diffrn_orient_matrix_UB_22      0.0402416000
_diffrn_orient_matrix_UB_23      -0.0285129000
_diffrn_orient_matrix_UB_31      0.0035100000
_diffrn_orient_matrix_UB_32      -0.0022161000
_diffrn_orient_matrix_UB_33      -0.0399386000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                13143
_reflns_number_total             17016
_reflns_special_details          
;
 _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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1262
_refine_ls_number_reflns         17016
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.030
_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)+(0.0835P)²+1.3979P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1662
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5619(15)
 0.4381(15)
2. 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
3. Restrained distances
 O24-H24
 0.85 with sigma of 0.01
 O29-H29
 0.85 with sigma of 0.01
 O4-H4c
 0.85 with sigma of 0.01
 O9-H9a
 0.85 with sigma of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C50(H50a,H50b), C10(H10c,H10d), C36(H36a,H36b), C76(H76a,H76b)
4.b Aromatic/amide H refined with riding coordinates:
 C57(H57), C58(H58), C44(H44), C52(H52), C48(H48), C24(H24a), C23(H23),
 C64(H64), C63(H63), C12(H12), C4(H4), C8(H8), C17(H17), C18(H18), C38(H38),
 C34(H34), C30(H30), C74(H74), C70(H70), C80(H80)
4.c Idealised Me refined as rotating group:
 C41(H41a,H41b,H41c), C42(H42a,H42b,H42c), C43(H43a,H43b,H43c), C2(H2c,H2d,
 H2e), C1(H1a,H1b,H1c), C3(H3a,H3b,H3c), C28(H28a,H28b,H28c), C27(H27a,H27b,
 H27c), C29(H29a,H29b,H29c), C68(H68a,H68b,H68c), C69(H69a,H69b,H69c), C67(H67a,
 H67b,H67c)
;
_atom_sites_solution_hydrogens   mixed
_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
O21 O 0.13978(12) -0.59347(12) 1.67663(12) 0.0231(4) Uani 1 1 d . . . . .
O20 O 0.00313(11) -0.63773(13) 1.71093(12) 0.0260(4) Uani 1 1 d . . . . .
O24 O 0.10535(13) -0.55464(14) 1.29871(13) 0.0304(5) Uani 1 1 d D . . . .
H24 H 0.079(3) -0.568(3) 1.274(3) 0.107(19) Uiso 1 1 d D . . . .
O23 O -0.02116(12) -0.60957(14) 1.42899(13) 0.0312(5) Uani 1 1 d . . . . .
O22 O 0.05655(11) -0.59469(11) 1.52676(11) 0.0183(4) Uani 1 1 d . . . . .
C55 C 0.08038(16) -0.60715(16) 1.65602(17) 0.0181(5) Uani 1 1 d . . . . .
C56 C 0.11417(16) -0.58353(16) 1.55696(17) 0.0179(5) Uani 1 1 d . . . . .
C60 C 0.05678(17) -0.58035(17) 1.38548(17) 0.0213(5) Uani 1 1 d . . . . .
C57 C 0.19586(17) -0.55329(17) 1.48635(17) 0.0197(5) Uani 1 1 d . . . . .
H57 H 0.2471 -0.5400 1.4895 0.024 Uiso 1 1 calc R U . . .
C58 C 0.18995(16) -0.54534(17) 1.40658(17) 0.0195(5) Uani 1 1 d . . . . .
H58 H 0.2364 -0.5260 1.3460 0.023 Uiso 1 1 calc R U . . .
C59 C 0.10446(17) -0.57088(17) 1.43439(17) 0.0190(5) Uani 1 1 d . . . . .
H29 H 0.113(3) -0.618(3) 0.7809(9) 0.094(17) Uiso 1 1 d D . . . .
O18 O -0.10611(12) 0.10491(12) 0.65534(13) 0.0251(4) Uani 1 1 d . . . . .
O17 O 0.06446(13) 0.17001(12) 0.56334(15) 0.0330(5) Uani 1 1 d . . . . .
O19 O -0.15717(12) -0.05639(13) 0.69577(15) 0.0333(5) Uani 1 1 d . . . . .
N11 N 0.21538(14) -0.21281(14) 0.75772(15) 0.0207(5) Uani 1 1 d . . . . .
N12 N 0.25397(15) -0.07475(15) 0.63911(17) 0.0216(5) Uani 1 1 d . . . . .
N10 N 0.18081(16) -0.35425(16) 0.87504(16) 0.0255(5) Uani 1 1 d . . . . .
N9 N 0.14617(14) -0.32348(15) 0.75413(15) 0.0213(5) Uani 1 1 d . . . . .
C47 C 0.04606(18) 0.08616(17) 0.58007(18) 0.0230(6) Uani 1 1 d . . . . .
C44 C -0.00554(17) -0.08508(17) 0.62566(18) 0.0221(6) Uani 1 1 d . . . . .
H44 H -0.0230 -0.1435 0.6414 0.026 Uiso 1 1 calc R U . . .
C54 C 0.21290(16) -0.15476(16) 0.67800(17) 0.0178(5) Uani 1 1 d . . . . .
C52 C 0.13637(16) -0.26372(17) 0.67821(17) 0.0200(5) Uani 1 1 d . . . . .
H52 H 0.1075 -0.2830 0.6531 0.024 Uiso 1 1 calc R U . . .
C51 C 0.16653(16) -0.17776(16) 0.63763(17) 0.0175(5) Uani 1 1 d . . . . .
C49 C 0.08318(16) -0.05220(17) 0.57842(17) 0.0188(5) Uani 1 1 d . . . . .
C45 C -0.06843(17) -0.03176(18) 0.64970(19) 0.0234(6) Uani 1 1 d . . . . .
C46 C -0.04256(17) 0.05344(17) 0.62838(18) 0.0226(6) Uani 1 1 d . . . . .
C48 C 0.10908(17) 0.03357(17) 0.55414(17) 0.0218(6) Uani 1 1 d . . . . .
H48 H 0.1696 0.0563 0.5199 0.026 Uiso 1 1 calc R U . . .
C41 C -0.18696(19) -0.1418(2) 0.7164(3) 0.0417(8) Uani 1 1 d . . . . .
H41A H -0.1633 -0.1484 0.6593 0.063 Uiso 1 1 calc R U . . .
H41B H -0.2514 -0.1499 0.7442 0.063 Uiso 1 1 calc R U . . .
H41C H -0.1667 -0.1859 0.7600 0.063 Uiso 1 1 calc R U . . .
C42 C -0.1179(2) 0.1030(2) 0.7402(2) 0.0324(7) Uani 1 1 d . . . . .
H42A H -0.0649 0.1322 0.7304 0.049 Uiso 1 1 calc R U . . .
H42B H -0.1286 0.0420 0.7874 0.049 Uiso 1 1 calc R U . . .
H42C H -0.1684 0.1335 0.7611 0.049 Uiso 1 1 calc R U . . .
C43 C 0.1548(2) 0.2042(2) 0.5179(2) 0.0409(8) Uani 1 1 d . . . . .
H43A H 0.1814 0.2082 0.4555 0.061 Uiso 1 1 calc R U . . .
H43B H 0.1854 0.1653 0.5532 0.061 Uiso 1 1 calc R U . . .
H43C H 0.1598 0.2627 0.5138 0.061 Uiso 1 1 calc R U . . .
C53 C 0.18092(16) -0.29601(17) 0.79533(17) 0.0204(5) Uani 1 1 d . . . . .
C50 C 0.15216(17) -0.11166(17) 0.55523(17) 0.0204(5) Uani 1 1 d . . . . .
H50A H 0.1339 -0.1436 0.5296 0.024 Uiso 1 1 calc R U . . .
H50B H 0.2086 -0.0749 0.5066 0.024 Uiso 1 1 calc R U . . .
O13 O 0.36506(12) -0.00627(12) 0.70364(12) 0.0219(4) Uani 1 1 d . . . . .
O10 O 0.32631(12) 0.04386(13) 0.42620(12) 0.0273(4) Uani 1 1 d . . . . .
O11 O 0.40457(11) 0.06697(11) 0.52017(11) 0.0166(4) Uani 1 1 d . . . . .
O9 O 0.44483(12) 0.11648(12) 0.29181(12) 0.0203(4) Uani 1 1 d D . . . .
O12 O 0.48373(12) 0.07179(12) 0.67208(12) 0.0225(4) Uani 1 1 d . . . . .
C26 C 0.43272(16) 0.04622(16) 0.64911(17) 0.0172(5) Uani 1 1 d . . . . .
C21 C 0.40046(16) 0.08452(16) 0.38051(17) 0.0175(5) Uani 1 1 d . . . . .
C25 C 0.46253(16) 0.08295(15) 0.54772(16) 0.0158(5) Uani 1 1 d . . . . .
C22 C 0.44840(16) 0.10047(16) 0.42592(16) 0.0165(5) Uani 1 1 d . . . . .
C24 C 0.53943(17) 0.12535(16) 0.47404(16) 0.0187(5) Uani 1 1 d . . . . .
H24A H 0.5898 0.1441 0.4751 0.022 Uiso 1 1 calc R U . . .
C23 C 0.53081(17) 0.13666(16) 0.39455(17) 0.0186(5) Uani 1 1 d . . . . .
H23 H 0.5741 0.1641 0.3321 0.022 Uiso 1 1 calc R U . . .
O29 O 0.09642(13) -0.63851(12) 0.83957(12) 0.0258(4) Uani 1 1 d D . . . .
O25 O 0.05316(13) -0.60580(13) 1.21816(12) 0.0292(5) Uani 1 1 d . . . . .
O26 O 0.10971(14) -0.47853(12) 1.08773(13) 0.0317(5) Uani 1 1 d . . . . .
O28 O 0.13293(14) -0.50011(12) 0.80495(13) 0.0292(4) Uani 1 1 d . . . . .
O27 O 0.09395(12) -0.55454(11) 0.98868(11) 0.0198(4) Uani 1 1 d . . . . .
C66 C 0.10605(17) -0.57805(16) 0.85928(17) 0.0186(5) Uani 1 1 d . . . . .
C61 C 0.07967(17) -0.55590(17) 1.13064(17) 0.0211(6) Uani 1 1 d . . . . .
C65 C 0.08344(16) -0.61191(17) 0.95901(17) 0.0190(5) Uani 1 1 d . . . . .
C62 C 0.07108(17) -0.60313(17) 1.08153(17) 0.0204(5) Uani 1 1 d . . . . .
C64 C 0.05441(17) -0.69370(17) 1.02963(17) 0.0201(5) Uani 1 1 d . . . . .
H64 H 0.0414 -0.7447 1.0266 0.024 Uiso 1 1 calc R U . . .
C63 C 0.04715(17) -0.68845(17) 1.10904(17) 0.0200(5) Uani 1 1 d . . . . .
H63 H 0.0291 -0.7353 1.1696 0.024 Uiso 1 1 calc R U . . .
O2 O 0.39109(12) 0.59796(12) -0.15125(13) 0.0263(4) Uani 1 1 d . . . . .
O3 O 0.32866(13) 0.42717(13) -0.04383(15) 0.0356(5) Uani 1 1 d . . . . .
O1 O 0.55731(14) 0.65561(12) -0.21030(16) 0.0358(5) Uani 1 1 d . . . . .
N3 N 0.71654(14) 0.28172(14) -0.25048(14) 0.0208(5) Uani 1 1 d . . . . .
N2 N 0.85503(16) 0.31372(17) -0.36980(16) 0.0261(5) Uani 1 1 d . . . . .
N1 N 0.82950(15) 0.35835(14) -0.25748(15) 0.0210(5) Uani 1 1 d . . . . .
N4 N 0.58055(15) 0.24539(15) -0.12923(17) 0.0224(5) Uani 1 1 d . . . . .
C14 C 0.79959(16) 0.31831(16) -0.29266(17) 0.0192(5) Uani 1 1 d . . . . .
C10 C 0.62248(17) 0.35320(17) -0.05613(17) 0.0202(5) Uani 1 1 d . . . . .
H10C H 0.6564 0.3749 -0.0345 0.024 Uiso 1 1 calc R U . . .
H10D H 0.5880 0.2966 -0.0049 0.024 Uiso 1 1 calc R U . . .
C11 C 0.68607(16) 0.33811(16) -0.13796(17) 0.0179(5) Uani 1 1 d . . . . .
C5 C 0.41496(17) 0.44967(18) -0.06966(19) 0.0244(6) Uani 1 1 d . . . . .
C6 C 0.44646(18) 0.53802(18) -0.12583(19) 0.0228(6) Uani 1 1 d . . . . .
C12 C 0.77173(17) 0.37079(16) -0.18317(17) 0.0203(5) Uani 1 1 d . . . . .
H12 H 0.7926 0.4035 -0.1627 0.024 Uiso 1 1 calc R U . . .
C4 C 0.47152(18) 0.38982(18) -0.04491(18) 0.0230(6) Uani 1 1 d . . . . .
H4 H 0.4499 0.3295 -0.0050 0.028 Uiso 1 1 calc R U . . .
C13 C 0.66089(17) 0.28774(16) -0.17249(17) 0.0185(5) Uani 1 1 d . . . . .
C2 C 0.3871(2) 0.6053(2) -0.2324(2) 0.0345(7) Uani 1 1 d . . . . .
H2C H 0.4469 0.6154 -0.2814 0.052 Uiso 1 1 calc R U . . .
H2D H 0.3550 0.6545 -0.2534 0.052 Uiso 1 1 calc R U . . .
H2E H 0.3565 0.5509 -0.2178 0.052 Uiso 1 1 calc R U . . .
C1 C 0.6446(2) 0.6885(2) -0.2396(3) 0.0488(9) Uani 1 1 d . . . . .
H1A H 0.6860 0.6642 -0.2799 0.073 Uiso 1 1 calc R U . . .
H1B H 0.6558 0.6713 -0.1854 0.073 Uiso 1 1 calc R U . . .
H1C H 0.6524 0.7526 -0.2737 0.073 Uiso 1 1 calc R U . . .
C3 C 0.2985(2) 0.3365(2) 0.0019(3) 0.0523(10) Uani 1 1 d . . . . .
H3A H 0.3365 0.3083 -0.0359 0.078 Uiso 1 1 calc R U . . .
H3B H 0.2380 0.3285 0.0111 0.078 Uiso 1 1 calc R U . . .
H3C H 0.3003 0.3098 0.0621 0.078 Uiso 1 1 calc R U . . .
C8 C 0.59057(18) 0.50744(17) -0.13369(19) 0.0234(6) Uani 1 1 d . . . . .
H8 H 0.6504 0.5271 -0.1552 0.028 Uiso 1 1 calc R U . . .
C7 C 0.53415(18) 0.56725(17) -0.15697(19) 0.0244(6) Uani 1 1 d . . . . .
C9 C 0.55928(17) 0.41859(17) -0.07871(17) 0.0202(5) Uani 1 1 d . . . . .
O7 O 0.46482(13) 0.17550(12) 0.08410(12) 0.0274(4) Uani 1 1 d . . . . .
O6 O 0.43878(11) 0.10214(11) -0.01058(11) 0.0173(4) Uani 1 1 d . . . . .
O8 O 0.38773(11) 0.05871(11) 0.21944(11) 0.0196(4) Uani 1 1 d . . . . .
O4 O 0.42635(12) 0.02636(12) -0.15957(12) 0.0238(4) Uani 1 1 d D . . . .
H4C H 0.449(2) 0.043(2) -0.2182(8) 0.046(10) Uiso 1 1 d D . . . .
O5 O 0.50822(12) 0.14487(12) -0.19525(12) 0.0226(4) Uani 1 1 d . . . . .
C15 C 0.45603(16) 0.07870(16) -0.14007(17) 0.0170(5) Uani 1 1 d . . . . .
C20 C 0.42107(16) 0.10382(16) 0.12984(17) 0.0181(5) Uani 1 1 d . . . . .
C19 C 0.40211(16) 0.05833(16) 0.08437(16) 0.0170(5) Uani 1 1 d . . . . .
C16 C 0.41935(16) 0.04733(16) -0.03890(17) 0.0179(5) Uani 1 1 d . . . . .
C17 C 0.37141(16) -0.02780(17) 0.03491(17) 0.0196(5) Uani 1 1 d . . . . .
H17 H 0.3495 -0.0759 0.0335 0.023 Uiso 1 1 calc R U . . .
C18 C 0.36021(17) -0.02089(17) 0.11495(17) 0.0203(5) Uani 1 1 d . . . . .
H18 H 0.3294 -0.0634 0.1775 0.024 Uiso 1 1 calc R U . . .
O16 O 0.04137(13) 0.06601(13) 1.11933(13) 0.0296(5) Uani 1 1 d . . . . .
O15 O 0.19937(13) 0.07789(13) 0.98061(15) 0.0312(5) Uani 1 1 d . . . . .
O14 O 0.21352(13) 0.11288(14) 0.81402(14) 0.0354(5) Uani 1 1 d . . . . .
N14 N -0.24385(13) 0.27000(13) 1.04029(13) 0.0162(4) Uani 1 1 d . . . . .
N13 N -0.10588(15) 0.30847(15) 0.92181(15) 0.0205(5) Uani 1 1 d . . . . .
N16 N -0.31542(15) 0.12772(15) 1.11111(17) 0.0264(5) Uani 1 1 d . . . . .
N15 N -0.38431(15) 0.23019(16) 1.15995(15) 0.0200(5) Uani 1 1 d . . . . .
C40 C -0.17594(16) 0.24885(16) 0.98054(16) 0.0160(5) Uani 1 1 d . . . . .
C38 C -0.24838(17) 0.10609(17) 1.04952(19) 0.0229(6) Uani 1 1 d . . . . .
H38 H -0.2508 0.0482 1.0558 0.027 Uiso 1 1 calc R U . . .
C32 C 0.12501(17) 0.09391(17) 0.9649(2) 0.0229(6) Uani 1 1 d . . . . .
C34 C 0.05864(17) 0.13182(17) 0.86016(18) 0.0226(6) Uani 1 1 d . . . . .
H34 H 0.0640 0.1474 0.8001 0.027 Uiso 1 1 calc R U . . .
C35 C -0.02266(17) 0.12704(16) 0.93050(17) 0.0193(5) Uani 1 1 d . . . . .
C31 C 0.04309(18) 0.08828(17) 1.03542(18) 0.0218(6) Uani 1 1 d . . . . .
C28 C 0.2249(2) 0.1416(2) 1.0003(2) 0.0363(7) Uani 1 1 d . . . . .
H28A H 0.1892 0.1275 1.0656 0.054 Uiso 1 1 calc R U . . .
H28B H 0.2159 0.2000 0.9613 0.054 Uiso 1 1 calc R U . . .
H28C H 0.2872 0.1407 0.9874 0.054 Uiso 1 1 calc R U . . .
C27 C 0.2259(2) 0.1454(2) 0.7209(2) 0.0396(8) Uani 1 1 d . . . . .
H27A H 0.1903 0.1064 0.7174 0.059 Uiso 1 1 calc R U . . .
H27B H 0.2881 0.1480 0.6808 0.059 Uiso 1 1 calc R U . . .
H27C H 0.2078 0.2044 0.7005 0.059 Uiso 1 1 calc R U . . .
C30 C -0.03080(17) 0.10472(16) 1.01796(18) 0.0206(5) Uani 1 1 d . . . . .
H30 H -0.0867 0.1006 1.0661 0.025 Uiso 1 1 calc R U . . .
C37 C -0.17882(16) 0.16515(16) 0.97990(16) 0.0161(5) Uani 1 1 d . . . . .
C39 C -0.31371(16) 0.20992(16) 1.10305(16) 0.0173(5) Uani 1 1 d . . . . .
C33 C 0.13208(17) 0.11385(17) 0.87756(19) 0.0245(6) Uani 1 1 d . . . . .
C36 C -0.10353(17) 0.14296(17) 0.91172(17) 0.0198(5) Uani 1 1 d . . . . .
H36A H -0.0869 0.1915 0.8489 0.024 Uiso 1 1 calc R U . . .
H36B H -0.1232 0.0897 0.9127 0.024 Uiso 1 1 calc R U . . .
C29 C -0.0408(2) 0.0646(2) 1.19133(19) 0.0331(7) Uani 1 1 d . . . . .
H29A H -0.0331 0.0509 1.2468 0.050 Uiso 1 1 calc R U . . .
H29B H -0.0839 0.0197 1.2055 0.050 Uiso 1 1 calc R U . . .
H29C H -0.0618 0.1221 1.1711 0.050 Uiso 1 1 calc R U . . .
O32 O 0.45199(13) -0.51989(13) 0.35735(14) 0.0320(5) Uani 1 1 d . . . . .
O31 O 0.43917(13) -0.68508(13) 0.48446(17) 0.0365(5) Uani 1 1 d . . . . .
O30 O 0.38491(15) -0.72382(13) 0.66216(16) 0.0411(6) Uani 1 1 d . . . . .
N7 N 0.23024(13) -0.25566(13) 0.46123(14) 0.0170(4) Uani 1 1 d . . . . .
N8 N 0.18477(15) -0.39593(15) 0.57569(16) 0.0213(5) Uani 1 1 d . . . . .
N5 N 0.27524(16) -0.11246(15) 0.34948(15) 0.0200(5) Uani 1 1 d . . . . .
N6 N 0.36958(14) -0.18741(14) 0.41100(15) 0.0200(5) Uani 1 1 d . . . . .
C78 C 0.24729(16) -0.32832(16) 0.52205(16) 0.0163(5) Uani 1 1 d . . . . .
C79 C 0.29141(16) -0.18562(16) 0.40767(16) 0.0168(5) Uani 1 1 d . . . . .
C77 C 0.32873(16) -0.33225(16) 0.52994(17) 0.0179(5) Uani 1 1 d . . . . .
C75 C 0.37028(16) -0.48601(17) 0.56599(18) 0.0197(5) Uani 1 1 d . . . . .
C71 C 0.42255(16) -0.53286(17) 0.44666(19) 0.0209(5) Uani 1 1 d . . . . .
C74 C 0.36324(17) -0.57168(17) 0.63159(19) 0.0249(6) Uani 1 1 d . . . . .
H74 H 0.3424 -0.5849 0.6949 0.030 Uiso 1 1 calc R U . . .
C68 C 0.3756(2) -0.7110(2) 0.4644(2) 0.0365(7) Uani 1 1 d . . . . .
H68A H 0.3180 -0.7280 0.5182 0.055 Uiso 1 1 calc R U . . .
H68B H 0.3935 -0.7608 0.4504 0.055 Uiso 1 1 calc R U . . .
H68C H 0.3718 -0.6618 0.4110 0.055 Uiso 1 1 calc R U . . .
C69 C 0.4501(2) -0.4351(2) 0.29111(19) 0.0330(7) Uani 1 1 d . . . . .
H69A H 0.3901 -0.4192 0.3117 0.050 Uiso 1 1 calc R U . . .
H69B H 0.4687 -0.4354 0.2313 0.050 Uiso 1 1 calc R U . . .
H69C H 0.4901 -0.3923 0.2847 0.050 Uiso 1 1 calc R U . . .
C67 C 0.3509(3) -0.7457(2) 0.7580(2) 0.0499(10) Uani 1 1 d . . . . .
H67A H 0.3469 -0.8093 0.7938 0.075 Uiso 1 1 calc R U . . .
H67B H 0.2923 -0.7269 0.7789 0.075 Uiso 1 1 calc R U . . .
H67C H 0.3902 -0.7159 0.7671 0.075 Uiso 1 1 calc R U . . .
C70 C 0.40009(16) -0.46658(16) 0.47376(18) 0.0194(5) Uani 1 1 d . . . . .
H70 H 0.4051 -0.4079 0.4292 0.023 Uiso 1 1 calc R U . . .
C80 C 0.38793(17) -0.26076(17) 0.47131(18) 0.0199(5) Uani 1 1 d . . . . .
H80 H 0.4438 -0.2611 0.4717 0.024 Uiso 1 1 calc R U . . .
C76 C 0.34789(17) -0.41409(17) 0.59663(18) 0.0207(5) Uani 1 1 d . . . . .
H76A H 0.2959 -0.4367 0.6576 0.025 Uiso 1 1 calc R U . . .
H76B H 0.3977 -0.3988 0.6046 0.025 Uiso 1 1 calc R U . . .
C73 C 0.38697(17) -0.63779(17) 0.6038(2) 0.0268(6) Uani 1 1 d . . . . .
C72 C 0.41575(17) -0.61910(17) 0.5114(2) 0.0259(6) Uani 1 1 d . . . . .
H9A H 0.430(4) 0.092(3) 0.267(4) 0.14(2) Uiso 1 1 d D . . . .
H5A H 0.223(2) -0.1102(18) 0.3534(19) 0.019(7) Uiso 1 1 d . . . . .
H5B H 0.314(2) -0.067(2) 0.318(2) 0.024(8) Uiso 1 1 d . . . . .
H10A H 0.1586(19) -0.409(2) 0.902(2) 0.025(8) Uiso 1 1 d . . . . .
H4A H 0.541(2) 0.238(2) -0.074(2) 0.034(9) Uiso 1 1 d . . . . .
H13A H -0.0597(19) 0.2979(18) 0.879(2) 0.021(7) Uiso 1 1 d . . . . .
H6 H 0.411(2) -0.140(2) 0.373(2) 0.034(9) Uiso 1 1 d . . . . .
H4B H 0.564(2) 0.216(2) -0.151(2) 0.032(9) Uiso 1 1 d . . . . .
H2A H 0.833(2) 0.287(2) -0.390(2) 0.038(9) Uiso 1 1 d . . . . .
H8A H 0.135(2) -0.3906(19) 0.571(2) 0.028(8) Uiso 1 1 d . . . . .
H10B H 0.201(2) -0.337(2) 0.904(2) 0.043(10) Uiso 1 1 d . . . . .
H15A H -0.435(2) 0.194(2) 1.192(2) 0.027(8) Uiso 1 1 d . . . . .
H1 H 0.884(2) 0.3764(19) -0.279(2) 0.025(8) Uiso 1 1 d . . . . .
H2B H 0.908(2) 0.342(2) -0.406(2) 0.030(8) Uiso 1 1 d . . . . .
H12A H 0.263(2) -0.040(2) 0.585(2) 0.034(9) Uiso 1 1 d . . . . .
H15B H -0.387(2) 0.284(2) 1.155(2) 0.034(9) Uiso 1 1 d . . . . .
H12B H 0.283(2) -0.062(2) 0.667(2) 0.051(11) Uiso 1 1 d . . . . .
H8B H 0.194(2) -0.445(2) 0.615(2) 0.047(10) Uiso 1 1 d . . . . .
H16 H -0.357(3) 0.085(3) 1.162(3) 0.068(13) Uiso 1 1 d . . . . .
H13B H -0.112(2) 0.363(2) 0.924(2) 0.050(10) Uiso 1 1 d . . . . .
H9 H 0.133(2) -0.383(2) 0.777(2) 0.037(9) Uiso 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
O21 C55 1.283(3) . ?
O20 C55 1.233(3) . ?
O24 H24 0.858(10) . ?
O24 C60 1.283(3) . ?
O23 C60 1.223(3) . ?
O22 C56 1.366(3) . ?
O22 C59 1.367(3) . ?
C55 C56 1.473(3) . ?
C56 C57 1.353(4) . ?
C60 C59 1.486(3) . ?
C57 H57 0.9500 . ?
C57 C58 1.420(3) . ?
C58 H58 0.9500 . ?
C58 C59 1.358(3) . ?
O18 C46 1.388(3) . ?
O18 C42 1.430(3) . ?
O17 C47 1.368(3) . ?
O17 C43 1.423(4) . ?
O19 C45 1.366(3) . ?
O19 C41 1.424(4) . ?
N11 C54 1.348(3) . ?
N11 C53 1.338(3) . ?
N12 C54 1.327(3) . ?
N12 H12A 0.83(3) . ?
N12 H12B 0.93(4) . ?
N10 C53 1.331(3) . ?
N10 H10A 0.88(3) . ?
N10 H10B 0.88(4) . ?
N9 C52 1.363(3) . ?
N9 C53 1.359(3) . ?
N9 H9 0.93(3) . ?
C47 C46 1.389(4) . ?
C47 C48 1.391(4) . ?
C44 H44 0.9500 . ?
C44 C49 1.392(4) . ?
C44 C45 1.390(4) . ?
C54 C51 1.447(3) . ?
C52 H52 0.9500 . ?
C52 C51 1.353(3) . ?
C51 C50 1.517(3) . ?
C49 C48 1.389(4) . ?
C49 C50 1.522(4) . ?
C45 C46 1.396(4) . ?
C48 H48 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
O13 C26 1.236(3) . ?
O10 C21 1.228(3) . ?
O11 C25 1.368(3) . ?
O11 C22 1.368(3) . ?
O9 C21 1.290(3) . ?
O9 H9A 0.856(10) . ?
O12 C26 1.283(3) . ?
C26 C25 1.485(3) . ?
C21 C22 1.485(3) . ?
C25 C24 1.347(3) . ?
C22 C23 1.353(3) . ?
C24 H24A 0.9500 . ?
C24 C23 1.420(3) . ?
C23 H23 0.9500 . ?
O29 H29 0.862(10) . ?
O29 C66 1.276(3) . ?
O25 C61 1.291(3) . ?
O26 C61 1.222(3) . ?
O28 C66 1.232(3) . ?
O27 C65 1.362(3) . ?
O27 C62 1.374(3) . ?
C66 C65 1.486(3) . ?
C61 C62 1.486(4) . ?
C65 C64 1.352(4) . ?
C62 C63 1.358(4) . ?
C64 H64 0.9500 . ?
C64 C63 1.416(4) . ?
C63 H63 0.9500 . ?
O2 C6 1.387(3) . ?
O2 C2 1.432(3) . ?
O3 C5 1.367(3) . ?
O3 C3 1.416(4) . ?
O1 C1 1.418(4) . ?
O1 C7 1.366(3) . ?
N3 C14 1.333(3) . ?
N3 C13 1.351(3) . ?
N2 C14 1.327(3) . ?
N2 H2A 0.89(4) . ?
N2 H2B 0.87(3) . ?
N1 C14 1.358(3) . ?
N1 C12 1.366(3) . ?
N1 H1 0.87(3) . ?
N4 C13 1.326(3) . ?
N4 H4A 0.89(3) . ?
N4 H4B 0.89(3) . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 C11 1.516(4) . ?
C10 C9 1.524(3) . ?
C11 C12 1.348(4) . ?
C11 C13 1.441(3) . ?
C5 C6 1.388(4) . ?
C5 C4 1.398(4) . ?
C6 C7 1.397(4) . ?
C12 H12 0.9500 . ?
C4 H4 0.9500 . ?
C4 C9 1.386(4) . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C7 1.388(4) . ?
C8 C9 1.393(4) . ?
O7 C20 1.218(3) . ?
O6 C19 1.374(3) . ?
O6 C16 1.367(3) . ?
O8 C20 1.301(3) . ?
O4 H4C 0.858(10) . ?
O4 C15 1.300(3) . ?
O5 C15 1.219(3) . ?
C15 C16 1.479(3) . ?
C20 C19 1.485(3) . ?
C19 C18 1.353(4) . ?
C16 C17 1.352(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.419(4) . ?
C18 H18 0.9500 . ?
O16 C31 1.364(3) . ?
O16 C29 1.427(3) . ?
O15 C32 1.386(3) . ?
O15 C28 1.435(3) . ?
O14 C27 1.426(4) . ?
O14 C33 1.365(3) . ?
N14 C40 1.344(3) . ?
N14 C39 1.334(3) . ?
N13 C40 1.326(3) . ?
N13 H13A 0.90(3) . ?
N13 H13B 0.95(4) . ?
N16 C38 1.360(3) . ?
N16 C39 1.352(3) . ?
N16 H16 0.91(4) . ?
N15 C39 1.334(3) . ?
N15 H15A 0.91(3) . ?
N15 H15B 0.89(3) . ?
C40 C37 1.444(3) . ?
C38 H38 0.9500 . ?
C38 C37 1.344(4) . ?
C32 C31 1.393(4) . ?
C32 C33 1.396(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.389(3) . ?
C34 C33 1.387(4) . ?
C35 C30 1.382(4) . ?
C35 C36 1.523(4) . ?
C31 C30 1.395(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C30 H30 0.9500 . ?
C37 C36 1.498(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
O32 C71 1.369(3) . ?
O32 C69 1.421(3) . ?
O31 C68 1.432(3) . ?
O31 C72 1.379(3) . ?
O30 C67 1.427(4) . ?
O30 C73 1.372(3) . ?
N7 C78 1.351(3) . ?
N7 C79 1.338(3) . ?
N8 C78 1.324(3) . ?
N8 H8A 0.88(3) . ?
N8 H8B 0.87(4) . ?
N5 C79 1.327(3) . ?
N5 H5A 0.87(3) . ?
N5 H5B 0.86(3) . ?
N6 C79 1.350(3) . ?
N6 C80 1.364(3) . ?
N6 H6 0.91(3) . ?
C78 C77 1.441(3) . ?
C77 C80 1.338(4) . ?
C77 C76 1.506(3) . ?
C75 C74 1.391(4) . ?
C75 C70 1.385(4) . ?
C75 C76 1.515(4) . ?
C71 C70 1.385(4) . ?
C71 C72 1.393(4) . ?
C74 H74 0.9500 . ?
C74 C73 1.390(4) . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C70 H70 0.9500 . ?
C80 H80 0.9500 . ?
C76 H76A 0.9900 . ?
C76 H76B 0.9900 . ?
C73 C72 1.394(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C60 O24 H24 111(3) . . ?
C56 O22 C59 106.17(19) . . ?
O21 C55 C56 112.7(2) . . ?
O20 C55 O21 125.7(2) . . ?
O20 C55 C56 121.6(2) . . ?
O22 C56 C55 117.9(2) . . ?
C57 C56 O22 110.6(2) . . ?
C57 C56 C55 131.5(2) . . ?
O24 C60 C59 113.1(2) . . ?
O23 C60 O24 127.5(2) . . ?
O23 C60 C59 119.4(2) . . ?
C56 C57 H57 126.7 . . ?
C56 C57 C58 106.6(2) . . ?
C58 C57 H57 126.7 . . ?
C57 C58 H58 126.9 . . ?
C59 C58 C57 106.2(2) . . ?
C59 C58 H58 126.9 . . ?
O22 C59 C60 116.7(2) . . ?
C58 C59 O22 110.5(2) . . ?
C58 C59 C60 132.8(2) . . ?
C46 O18 C42 112.1(2) . . ?
C47 O17 C43 116.9(2) . . ?
C45 O19 C41 117.0(2) . . ?
C53 N11 C54 118.4(2) . . ?
C54 N12 H12A 119(2) . . ?
C54 N12 H12B 120(2) . . ?
H12A N12 H12B 119(3) . . ?
C53 N10 H10A 122.0(19) . . ?
C53 N10 H10B 120(2) . . ?
H10A N10 H10B 118(3) . . ?
C52 N9 H9 122(2) . . ?
C53 N9 C52 119.7(2) . . ?
C53 N9 H9 118(2) . . ?
O17 C47 C46 115.4(2) . . ?
O17 C47 C48 124.6(2) . . ?
C46 C47 C48 120.0(2) . . ?
C49 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
C45 C44 C49 119.5(2) . . ?
N11 C54 C51 121.9(2) . . ?
N12 C54 N11 116.5(2) . . ?
N12 C54 C51 121.6(2) . . ?
N9 C52 H52 119.0 . . ?
C51 C52 N9 121.9(2) . . ?
C51 C52 H52 119.0 . . ?
C54 C51 C50 123.5(2) . . ?
C52 C51 C54 115.4(2) . . ?
C52 C51 C50 121.2(2) . . ?
C44 C49 C50 119.5(2) . . ?
C48 C49 C44 120.6(2) . . ?
C48 C49 C50 120.0(2) . . ?
O19 C45 C44 124.9(2) . . ?
O19 C45 C46 114.9(2) . . ?
C44 C45 C46 120.1(2) . . ?
O18 C46 C47 120.6(2) . . ?
O18 C46 C45 119.4(2) . . ?
C47 C46 C45 120.0(2) . . ?
C47 C48 H48 120.1 . . ?
C49 C48 C47 119.8(2) . . ?
C49 C48 H48 120.1 . . ?
O19 C41 H41A 109.5 . . ?
O19 C41 H41B 109.5 . . ?
O19 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O18 C42 H42A 109.5 . . ?
O18 C42 H42B 109.5 . . ?
O18 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O17 C43 H43A 109.5 . . ?
O17 C43 H43B 109.5 . . ?
O17 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N11 C53 N9 121.9(2) . . ?
N10 C53 N11 119.7(2) . . ?
N10 C53 N9 118.5(2) . . ?
C51 C50 C49 113.7(2) . . ?
C51 C50 H50A 108.8 . . ?
C51 C50 H50B 108.8 . . ?
C49 C50 H50A 108.8 . . ?
C49 C50 H50B 108.8 . . ?
H50A C50 H50B 107.7 . . ?
C22 O11 C25 105.79(18) . . ?
C21 O9 H9A 115(4) . . ?
O13 C26 O12 125.4(2) . . ?
O13 C26 C25 120.2(2) . . ?
O12 C26 C25 114.4(2) . . ?
O10 C21 O9 125.8(2) . . ?
O10 C21 C22 121.0(2) . . ?
O9 C21 C22 113.3(2) . . ?
O11 C25 C26 116.3(2) . . ?
C24 C25 O11 110.6(2) . . ?
C24 C25 C26 133.0(2) . . ?
O11 C22 C21 115.6(2) . . ?
C23 C22 O11 110.8(2) . . ?
C23 C22 C21 133.4(2) . . ?
C25 C24 H24A 126.6 . . ?
C25 C24 C23 106.8(2) . . ?
C23 C24 H24A 126.6 . . ?
C22 C23 C24 106.0(2) . . ?
C22 C23 H23 127.0 . . ?
C24 C23 H23 127.0 . . ?
C66 O29 H29 110(3) . . ?
C65 O27 C62 105.91(19) . . ?
O29 C66 C65 112.2(2) . . ?
O28 C66 O29 126.8(2) . . ?
O28 C66 C65 121.0(2) . . ?
O25 C61 C62 112.4(2) . . ?
O26 C61 O25 127.4(2) . . ?
O26 C61 C62 120.1(2) . . ?
O27 C65 C66 118.2(2) . . ?
C64 C65 O27 110.8(2) . . ?
C64 C65 C66 131.0(2) . . ?
O27 C62 C61 116.8(2) . . ?
C63 C62 O27 110.3(2) . . ?
C63 C62 C61 132.8(2) . . ?
C65 C64 H64 126.7 . . ?
C65 C64 C63 106.6(2) . . ?
C63 C64 H64 126.7 . . ?
C62 C63 C64 106.4(2) . . ?
C62 C63 H63 126.8 . . ?
C64 C63 H63 126.8 . . ?
C6 O2 C2 112.3(2) . . ?
C5 O3 C3 116.9(2) . . ?
C7 O1 C1 116.8(2) . . ?
C14 N3 C13 118.3(2) . . ?
C14 N2 H2A 117(2) . . ?
C14 N2 H2B 125(2) . . ?
H2A N2 H2B 118(3) . . ?
C14 N1 C12 119.8(2) . . ?
C14 N1 H1 124(2) . . ?
C12 N1 H1 116(2) . . ?
C13 N4 H4A 124(2) . . ?
C13 N4 H4B 122(2) . . ?
H4A N4 H4B 113(3) . . ?
N3 C14 N1 121.7(2) . . ?
N2 C14 N3 119.2(2) . . ?
N2 C14 N1 119.1(2) . . ?
H10C C10 H10D 107.8 . . ?
C11 C10 H10C 108.9 . . ?
C11 C10 H10D 108.9 . . ?
C11 C10 C9 113.2(2) . . ?
C9 C10 H10C 108.9 . . ?
C9 C10 H10D 108.9 . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 C13 115.1(2) . . ?
C13 C11 C10 123.4(2) . . ?
O3 C5 C6 116.0(2) . . ?
O3 C5 C4 124.2(3) . . ?
C6 C5 C4 119.8(2) . . ?
O2 C6 C5 120.3(2) . . ?
O2 C6 C7 119.5(2) . . ?
C5 C6 C7 120.2(2) . . ?
N1 C12 H12 119.0 . . ?
C11 C12 N1 122.1(2) . . ?
C11 C12 H12 119.0 . . ?
C5 C4 H4 120.1 . . ?
C9 C4 C5 119.8(3) . . ?
C9 C4 H4 120.1 . . ?
N3 C13 C11 122.4(2) . . ?
N4 C13 N3 116.4(2) . . ?
N4 C13 C11 121.2(2) . . ?
O2 C2 H2C 109.5 . . ?
O2 C2 H2D 109.5 . . ?
O2 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
O1 C7 C6 115.1(2) . . ?
O1 C7 C8 125.0(2) . . ?
C8 C7 C6 119.9(2) . . ?
C4 C9 C10 120.2(2) . . ?
C4 C9 C8 120.4(2) . . ?
C8 C9 C10 119.4(2) . . ?
C16 O6 C19 106.03(18) . . ?
C15 O4 H4C 111(2) . . ?
O4 C15 C16 111.2(2) . . ?
O5 C15 O4 126.6(2) . . ?
O5 C15 C16 122.2(2) . . ?
O7 C20 O8 126.2(2) . . ?
O7 C20 C19 120.7(2) . . ?
O8 C20 C19 113.1(2) . . ?
O6 C19 C20 115.1(2) . . ?
C18 C19 O6 110.5(2) . . ?
C18 C19 C20 134.3(2) . . ?
O6 C16 C15 116.2(2) . . ?
C17 C16 O6 110.4(2) . . ?
C17 C16 C15 133.4(2) . . ?
C16 C17 H17 126.6 . . ?
C16 C17 C18 106.8(2) . . ?
C18 C17 H17 126.6 . . ?
C19 C18 C17 106.3(2) . . ?
C19 C18 H18 126.9 . . ?
C17 C18 H18 126.9 . . ?
C31 O16 C29 117.0(2) . . ?
C32 O15 C28 113.7(2) . . ?
C33 O14 C27 117.0(2) . . ?
C39 N14 C40 118.4(2) . . ?
C40 N13 H13A 120.1(18) . . ?
C40 N13 H13B 115(2) . . ?
H13A N13 H13B 125(3) . . ?
C38 N16 H16 119(3) . . ?
C39 N16 C38 120.4(2) . . ?
C39 N16 H16 120(3) . . ?
C39 N15 H15A 118.8(19) . . ?
C39 N15 H15B 121(2) . . ?
H15A N15 H15B 117(3) . . ?
N14 C40 C37 121.8(2) . . ?
N13 C40 N14 117.0(2) . . ?
N13 C40 C37 121.3(2) . . ?
N16 C38 H38 119.4 . . ?
C37 C38 N16 121.2(2) . . ?
C37 C38 H38 119.4 . . ?
O15 C32 C31 121.0(2) . . ?
O15 C32 C33 119.4(2) . . ?
C31 C32 C33 119.6(2) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.0(3) . . ?
C34 C35 C36 119.5(2) . . ?
C30 C35 C34 120.3(2) . . ?
C30 C35 C36 120.1(2) . . ?
O16 C31 C32 115.9(2) . . ?
O16 C31 C30 124.1(2) . . ?
C32 C31 C30 120.0(2) . . ?
O15 C28 H28A 109.5 . . ?
O15 C28 H28B 109.5 . . ?
O15 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O14 C27 H27A 109.5 . . ?
O14 C27 H27B 109.5 . . ?
O14 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C35 C30 C31 120.0(2) . . ?
C35 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C40 C37 C36 121.3(2) . . ?
C38 C37 C40 115.9(2) . . ?
C38 C37 C36 122.4(2) . . ?
N14 C39 N16 121.7(2) . . ?
N15 C39 N14 120.1(2) . . ?
N15 C39 N16 118.2(2) . . ?
O14 C33 C32 115.9(2) . . ?
O14 C33 C34 124.0(3) . . ?
C34 C33 C32 120.1(2) . . ?
C35 C36 H36A 108.8 . . ?
C35 C36 H36B 108.8 . . ?
C37 C36 C35 113.8(2) . . ?
C37 C36 H36A 108.8 . . ?
C37 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?
O16 C29 H29A 109.5 . . ?
O16 C29 H29B 109.5 . . ?
O16 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C71 O32 C69 117.3(2) . . ?
C72 O31 C68 113.2(2) . . ?
C73 O30 C67 116.3(2) . . ?
C79 N7 C78 118.1(2) . . ?
C78 N8 H8A 119.1(19) . . ?
C78 N8 H8B 120(2) . . ?
H8A N8 H8B 121(3) . . ?
C79 N5 H5A 117.6(18) . . ?
C79 N5 H5B 118(2) . . ?
H5A N5 H5B 123(3) . . ?
C79 N6 C80 120.7(2) . . ?
C79 N6 H6 121(2) . . ?
C80 N6 H6 119(2) . . ?
N7 C78 C77 122.1(2) . . ?
N8 C78 N7 116.8(2) . . ?
N8 C78 C77 121.1(2) . . ?
N7 C79 N6 121.7(2) . . ?
N5 C79 N7 119.4(2) . . ?
N5 C79 N6 118.9(2) . . ?
C78 C77 C76 121.7(2) . . ?
C80 C77 C78 116.2(2) . . ?
C80 C77 C76 122.0(2) . . ?
C74 C75 C76 118.9(2) . . ?
C70 C75 C74 120.4(2) . . ?
C70 C75 C76 120.7(2) . . ?
O32 C71 C70 123.9(2) . . ?
O32 C71 C72 115.6(2) . . ?
C70 C71 C72 120.5(2) . . ?
C75 C74 H74 120.3 . . ?
C73 C74 C75 119.5(3) . . ?
C73 C74 H74 120.3 . . ?
O31 C68 H68A 109.5 . . ?
O31 C68 H68B 109.5 . . ?
O31 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
O32 C69 H69A 109.5 . . ?
O32 C69 H69B 109.5 . . ?
O32 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
O30 C67 H67A 109.5 . . ?
O30 C67 H67B 109.5 . . ?
O30 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C75 C70 H70 120.1 . . ?
C71 C70 C75 119.9(2) . . ?
C71 C70 H70 120.1 . . ?
N6 C80 H80 119.4 . . ?
C77 C80 N6 121.2(2) . . ?
C77 C80 H80 119.4 . . ?
C77 C76 C75 113.7(2) . . ?
C77 C76 H76A 108.8 . . ?
C77 C76 H76B 108.8 . . ?
C75 C76 H76A 108.8 . . ?
C75 C76 H76B 108.8 . . ?
H76A C76 H76B 107.7 . . ?
O30 C73 C74 124.3(3) . . ?
O30 C73 C72 115.2(3) . . ?
C74 C73 C72 120.5(2) . . ?
O31 C72 C71 120.7(3) . . ?
O31 C72 C73 120.1(2) . . ?
C71 C72 C73 119.2(2) . . ?

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
O21 C55 C56 O22 -179.5(2) . . . . ?
O21 C55 C56 C57 2.4(4) . . . . ?
O20 C55 C56 O22 1.4(4) . . . . ?
O20 C55 C56 C57 -176.6(3) . . . . ?
O24 C60 C59 O22 178.3(2) . . . . ?
O24 C60 C59 C58 -4.5(4) . . . . ?
O23 C60 C59 O22 -1.1(4) . . . . ?
O23 C60 C59 C58 176.2(3) . . . . ?
O22 C56 C57 C58 -0.4(3) . . . . ?
C55 C56 C57 C58 177.7(3) . . . . ?
C56 O22 C59 C60 177.8(2) . . . . ?
C56 O22 C59 C58 0.0(3) . . . . ?
C56 C57 C58 C59 0.4(3) . . . . ?
C57 C58 C59 O22 -0.2(3) . . . . ?
C57 C58 C59 C60 -177.6(3) . . . . ?
C59 O22 C56 C55 -178.2(2) . . . . ?
C59 O22 C56 C57 0.3(3) . . . . ?
O17 C47 C46 O18 0.9(4) . . . . ?
O17 C47 C46 C45 -179.5(2) . . . . ?
O17 C47 C48 C49 177.1(2) . . . . ?
O19 C45 C46 O18 0.8(4) . . . . ?
O19 C45 C46 C47 -178.8(2) . . . . ?
N11 C54 C51 C52 -8.5(3) . . . . ?
N11 C54 C51 C50 171.8(2) . . . . ?
N12 C54 C51 C52 172.7(2) . . . . ?
N12 C54 C51 C50 -7.0(4) . . . . ?
N9 C52 C51 C54 2.5(3) . . . . ?
N9 C52 C51 C50 -177.8(2) . . . . ?
C44 C49 C48 C47 2.3(4) . . . . ?
C44 C49 C50 C51 -75.6(3) . . . . ?
C44 C45 C46 O18 -178.1(2) . . . . ?
C44 C45 C46 C47 2.3(4) . . . . ?
C54 N11 C53 N10 -178.6(2) . . . . ?
C54 N11 C53 N9 1.9(4) . . . . ?
C54 C51 C50 C49 -73.7(3) . . . . ?
C52 N9 C53 N11 -7.8(4) . . . . ?
C52 N9 C53 N10 172.7(2) . . . . ?
C52 C51 C50 C49 106.6(3) . . . . ?
C49 C44 C45 O19 179.9(2) . . . . ?
C49 C44 C45 C46 -1.4(4) . . . . ?
C45 C44 C49 C48 -0.9(4) . . . . ?
C45 C44 C49 C50 177.8(2) . . . . ?
C46 C47 C48 C49 -1.3(4) . . . . ?
C48 C47 C46 O18 179.5(2) . . . . ?
C48 C47 C46 C45 -0.9(4) . . . . ?
C48 C49 C50 C51 103.1(3) . . . . ?
C41 O19 C45 C44 -3.2(4) . . . . ?
C41 O19 C45 C46 178.0(3) . . . . ?
C42 O18 C46 C47 -83.5(3) . . . . ?
C42 O18 C46 C45 96.9(3) . . . . ?
C43 O17 C47 C46 177.1(2) . . . . ?
C43 O17 C47 C48 -1.4(4) . . . . ?
C53 N11 C54 N12 -174.7(2) . . . . ?
C53 N11 C54 C51 6.4(3) . . . . ?
C53 N9 C52 C51 5.2(4) . . . . ?
C50 C49 C48 C47 -176.4(2) . . . . ?
O13 C26 C25 O11 10.3(3) . . . . ?
O13 C26 C25 C24 -164.3(3) . . . . ?
O10 C21 C22 O11 0.1(3) . . . . ?
O10 C21 C22 C23 174.5(3) . . . . ?
O11 C25 C24 C23 -0.5(3) . . . . ?
O11 C22 C23 C24 -0.1(3) . . . . ?
O9 C21 C22 O11 -179.3(2) . . . . ?
O9 C21 C22 C23 -4.9(4) . . . . ?
O12 C26 C25 O11 -171.5(2) . . . . ?
O12 C26 C25 C24 13.8(4) . . . . ?
C26 C25 C24 C23 174.3(3) . . . . ?
C21 C22 C23 C24 -174.7(3) . . . . ?
C25 O11 C22 C21 175.4(2) . . . . ?
C25 O11 C22 C23 -0.2(3) . . . . ?
C25 C24 C23 C22 0.4(3) . . . . ?
C22 O11 C25 C26 -175.3(2) . . . . ?
C22 O11 C25 C24 0.5(3) . . . . ?
O29 C66 C65 O27 177.7(2) . . . . ?
O29 C66 C65 C64 -0.8(4) . . . . ?
O25 C61 C62 O27 177.2(2) . . . . ?
O25 C61 C62 C63 -5.5(4) . . . . ?
O26 C61 C62 O27 -3.3(4) . . . . ?
O26 C61 C62 C63 174.1(3) . . . . ?
O28 C66 C65 O27 -0.5(4) . . . . ?
O28 C66 C65 C64 -179.0(3) . . . . ?
O27 C65 C64 C63 -0.9(3) . . . . ?
O27 C62 C63 C64 -0.7(3) . . . . ?
C66 C65 C64 C63 177.7(3) . . . . ?
C61 C62 C63 C64 -178.1(3) . . . . ?
C65 O27 C62 C61 178.1(2) . . . . ?
C65 O27 C62 C63 0.1(3) . . . . ?
C65 C64 C63 C62 0.9(3) . . . . ?
C62 O27 C65 C66 -178.3(2) . . . . ?
C62 O27 C65 C64 0.5(3) . . . . ?
O2 C6 C7 O1 1.0(4) . . . . ?
O2 C6 C7 C8 -178.5(2) . . . . ?
O3 C5 C6 O2 1.1(4) . . . . ?
O3 C5 C6 C7 -179.0(2) . . . . ?
O3 C5 C4 C9 176.5(2) . . . . ?
C14 N3 C13 N4 -175.6(2) . . . . ?
C14 N3 C13 C11 5.2(4) . . . . ?
C14 N1 C12 C11 5.6(4) . . . . ?
C10 C11 C12 N1 -179.4(2) . . . . ?
C10 C11 C13 N3 173.8(2) . . . . ?
C10 C11 C13 N4 -5.3(4) . . . . ?
C11 C10 C9 C4 107.2(3) . . . . ?
C11 C10 C9 C8 -72.8(3) . . . . ?
C5 C6 C7 O1 -178.8(2) . . . . ?
C5 C6 C7 C8 1.7(4) . . . . ?
C5 C4 C9 C10 -176.9(2) . . . . ?
C5 C4 C9 C8 3.0(4) . . . . ?
C6 C5 C4 C9 -1.8(4) . . . . ?
C12 N1 C14 N3 -7.7(4) . . . . ?
C12 N1 C14 N2 174.0(2) . . . . ?
C12 C11 C13 N3 -7.0(3) . . . . ?
C12 C11 C13 N4 173.9(2) . . . . ?
C4 C5 C6 O2 179.6(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C13 N3 C14 N2 -179.4(2) . . . . ?
C13 N3 C14 N1 2.2(4) . . . . ?
C13 C11 C12 N1 1.4(4) . . . . ?
C2 O2 C6 C5 -86.3(3) . . . . ?
C2 O2 C6 C7 93.8(3) . . . . ?
C1 O1 C7 C6 177.0(3) . . . . ?
C1 O1 C7 C8 -3.5(4) . . . . ?
C3 O3 C5 C6 171.0(3) . . . . ?
C3 O3 C5 C4 -7.4(4) . . . . ?
C7 C8 C9 C10 178.1(2) . . . . ?
C7 C8 C9 C4 -1.8(4) . . . . ?
C9 C10 C11 C12 106.9(3) . . . . ?
C9 C10 C11 C13 -73.9(3) . . . . ?
C9 C8 C7 O1 -179.9(2) . . . . ?
C9 C8 C7 C6 -0.5(4) . . . . ?
O7 C20 C19 O6 1.3(3) . . . . ?
O7 C20 C19 C18 176.5(3) . . . . ?
O6 C19 C18 C17 0.3(3) . . . . ?
O6 C16 C17 C18 -0.5(3) . . . . ?
O8 C20 C19 O6 -177.7(2) . . . . ?
O8 C20 C19 C18 -2.5(4) . . . . ?
O4 C15 C16 O6 -173.3(2) . . . . ?
O4 C15 C16 C17 9.4(4) . . . . ?
O5 C15 C16 O6 7.7(4) . . . . ?
O5 C15 C16 C17 -169.6(3) . . . . ?
C15 C16 C17 C18 176.8(3) . . . . ?
C20 C19 C18 C17 -175.0(3) . . . . ?
C19 O6 C16 C15 -177.1(2) . . . . ?
C19 O6 C16 C17 0.7(3) . . . . ?
C16 O6 C19 C20 175.7(2) . . . . ?
C16 O6 C19 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
O16 C31 C30 C35 179.9(2) . . . . ?
O15 C32 C31 O16 -0.2(4) . . . . ?
O15 C32 C31 C30 180.0(2) . . . . ?
O15 C32 C33 O14 2.2(4) . . . . ?
O15 C32 C33 C34 -178.7(2) . . . . ?
N14 C40 C37 C38 -7.9(3) . . . . ?
N14 C40 C37 C36 178.7(2) . . . . ?
N13 C40 C37 C38 172.2(2) . . . . ?
N13 C40 C37 C36 -1.2(4) . . . . ?
N16 C38 C37 C40 6.0(4) . . . . ?
N16 C38 C37 C36 179.2(2) . . . . ?
C40 N14 C39 N16 3.8(3) . . . . ?
C40 N14 C39 N15 -176.2(2) . . . . ?
C40 C37 C36 C35 71.5(3) . . . . ?
C38 N16 C39 N14 -5.8(4) . . . . ?
C38 N16 C39 N15 174.2(2) . . . . ?
C38 C37 C36 C35 -101.5(3) . . . . ?
C32 C31 C30 C35 -0.3(4) . . . . ?
C34 C35 C30 C31 1.0(4) . . . . ?
C34 C35 C36 C37 -160.9(2) . . . . ?
C35 C34 C33 O14 176.8(2) . . . . ?
C35 C34 C33 C32 -2.2(4) . . . . ?
C31 C32 C33 O14 -176.2(2) . . . . ?
C31 C32 C33 C34 2.9(4) . . . . ?
C28 O15 C32 C31 -66.5(3) . . . . ?
C28 O15 C32 C33 115.2(3) . . . . ?
C27 O14 C33 C32 -171.0(3) . . . . ?
C27 O14 C33 C34 10.0(4) . . . . ?
C30 C35 C36 C37 21.5(3) . . . . ?
C39 N14 C40 N13 -177.0(2) . . . . ?
C39 N14 C40 C37 3.1(3) . . . . ?
C39 N16 C38 C37 0.5(4) . . . . ?
C33 C32 C31 O16 178.1(2) . . . . ?
C33 C32 C31 C30 -1.6(4) . . . . ?
C33 C34 C35 C30 0.2(4) . . . . ?
C33 C34 C35 C36 -177.3(2) . . . . ?
C36 C35 C30 C31 178.6(2) . . . . ?
C29 O16 C31 C32 176.6(2) . . . . ?
C29 O16 C31 C30 -3.6(4) . . . . ?
O32 C71 C70 C75 179.5(2) . . . . ?
O32 C71 C72 O31 1.1(4) . . . . ?
O32 C71 C72 C73 179.5(2) . . . . ?
O30 C73 C72 O31 0.4(4) . . . . ?
O30 C73 C72 C71 -178.0(2) . . . . ?
N7 C78 C77 C80 -2.2(4) . . . . ?
N7 C78 C77 C76 -178.8(2) . . . . ?
N8 C78 C77 C80 178.9(2) . . . . ?
N8 C78 C77 C76 2.3(4) . . . . ?
C78 N7 C79 N5 -177.8(2) . . . . ?
C78 N7 C79 N6 2.4(3) . . . . ?
C78 C77 C80 N6 3.0(4) . . . . ?
C78 C77 C76 C75 74.5(3) . . . . ?
C79 N7 C78 N8 178.4(2) . . . . ?
C79 N7 C78 C77 -0.5(3) . . . . ?
C79 N6 C80 C77 -1.3(4) . . . . ?
C75 C74 C73 O30 178.1(2) . . . . ?
C75 C74 C73 C72 -1.4(4) . . . . ?
C74 C75 C70 C71 0.4(4) . . . . ?
C74 C75 C76 C77 -160.8(2) . . . . ?
C74 C73 C72 O31 180.0(2) . . . . ?
C74 C73 C72 C71 1.6(4) . . . . ?
C68 O31 C72 C71 -75.3(3) . . . . ?
C68 O31 C72 C73 106.3(3) . . . . ?
C69 O32 C71 C70 -7.0(4) . . . . ?
C69 O32 C71 C72 172.8(2) . . . . ?
C67 O30 C73 C74 3.9(4) . . . . ?
C67 O30 C73 C72 -176.5(3) . . . . ?
C70 C75 C74 C73 0.4(4) . . . . ?
C70 C75 C76 C77 21.3(3) . . . . ?
C70 C71 C72 O31 -179.1(2) . . . . ?
C70 C71 C72 C73 -0.7(4) . . . . ?
C80 N6 C79 N7 -1.6(4) . . . . ?
C80 N6 C79 N5 178.6(2) . . . . ?
C80 C77 C76 C75 -101.9(3) . . . . ?
C76 C77 C80 N6 179.6(2) . . . . ?
C76 C75 C74 C73 -177.4(2) . . . . ?
C76 C75 C70 C71 178.2(2) . . . . ?
C72 C71 C70 C75 -0.2(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.878
_oxdiff_exptl_absorpt_empirical_full_min 0.562
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5619(15)
2 0.4381(15)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_r20230324d_autored
_database_code_depnum_ccdc_archive 'CCDC 2288509'
loop_
_audit_author_name
_audit_author_address
'Liang Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2024-05-19 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C5 H3 O3 S), C14 H20 N4 O3, 2(C H4 O)'
_chemical_formula_sum            'C26 H34 N4 O11 S2'
_chemical_formula_weight         642.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
S S 0.1246 0.1234 '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                   11.43180(10)
_cell_length_b                   11.93110(10)
_cell_length_c                   12.8427(2)
_cell_angle_alpha                83.4930(10)
_cell_angle_beta                 68.6770(10)
_cell_angle_gamma                61.8010(10)
_cell_volume                     1434.43(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18251
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.7140
_cell_measurement_theta_min      1.9340
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37718
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.708
_diffrn_reflns_theta_min         1.942
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    0.50    --  -20.00   0.00  90.00  360
  2  ω   -110.00  55.00   0.50    0.50    --  -20.00   0.00   0.00  330
  3  ω   -110.00   7.00   0.50    0.50    --  -20.00 -70.00 180.00  234
  4  ω   -110.00   7.00   0.50    0.50    --  -20.00 -70.00   0.00  234
  5  ω   -110.00   7.00   0.50    0.50    --  -20.00 -70.00  90.00  234
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0146490000
_diffrn_orient_matrix_UB_12      -0.0630211000
_diffrn_orient_matrix_UB_13      -0.0114315000
_diffrn_orient_matrix_UB_21      -0.0729728000
_diffrn_orient_matrix_UB_22      0.0216485000
_diffrn_orient_matrix_UB_23      0.0105408000
_diffrn_orient_matrix_UB_31      0.0112931000
_diffrn_orient_matrix_UB_32      0.0115423000
_diffrn_orient_matrix_UB_33      -0.0573697000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9199
_reflns_number_total             11154
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         11154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.037
_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)+(0.0543P)²+0.5913P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1201
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C20(H20), C17(H17), C23(H23), C9(H9), C15(H15), C24(H24),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C3(H3C,H3D,H3E), C2(H2A,H2B,H2C), C25(H25A,H25B,H25C),
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_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
S01 S 0.67710(3) 0.68220(3) 0.03940(3) 0.01527(7) Uani 1 1 d . . . . .
S02 S 0.82195(3) 0.32831(3) 0.51774(3) 0.01437(7) Uani 1 1 d . . . . .
O2 O 0.27784(10) -0.01088(8) 0.67456(7) 0.01593(17) Uani 1 1 d . . . . .
O1 O 0.41857(10) -0.10954(8) 0.46276(8) 0.01759(17) Uani 1 1 d . . . . .
O3 O 0.12292(10) 0.24103(8) 0.72378(7) 0.01770(17) Uani 1 1 d . . . . .
O6 O 0.68427(9) 0.33308(8) 0.53679(8) 0.01726(17) Uani 1 1 d . . . . .
O8 O 0.77024(11) 0.62503(9) 0.10469(8) 0.01991(19) Uani 1 1 d . . . . .
O4 O 0.83402(10) 0.35067(9) 0.62058(8) 0.02066(19) Uani 1 1 d . . . . .
O7 O 0.54734(10) 0.66828(9) 0.09064(8) 0.02124(19) Uani 1 1 d . . . . .
O5 O 0.85089(10) 0.41014(8) 0.42923(8) 0.01954(18) Uani 1 1 d . . . . .
O9 O 0.74936(11) 0.63733(9) -0.07834(8) 0.02028(19) Uani 1 1 d . . . . .
O10 O 0.29359(12) 0.68554(10) 0.00974(9) 0.0248(2) Uani 1 1 d . . . . .
N2 N 0.52095(11) 0.49112(9) 0.23081(9) 0.01364(18) Uani 1 1 d . . . . .
O11 O 0.10793(14) 0.64465(11) -0.05002(10) 0.0314(2) Uani 1 1 d . . . . .
N1 N 0.37187(12) 0.48333(10) 0.15401(9) 0.01506(19) Uani 1 1 d . . . . .
N4 N 0.57338(11) 0.37081(10) 0.37696(9) 0.01452(18) Uani 1 1 d . . . . .
N3 N 0.67437(12) 0.50386(10) 0.30188(10) 0.01603(19) Uani 1 1 d . . . . .
C5 C 0.27323(12) 0.07021(11) 0.58890(10) 0.0132(2) Uani 1 1 d . . . . .
C14 C 0.43129(12) 0.44631(10) 0.23001(10) 0.01224(19) Uani 1 1 d . . . . .
C4 C 0.19570(12) 0.20236(11) 0.61290(10) 0.0138(2) Uani 1 1 d . . . . .
C22 C 0.51849(12) 0.93399(11) -0.00218(10) 0.0132(2) Uani 1 1 d . . . . .
C12 C 0.48182(13) 0.32492(11) 0.38143(10) 0.0147(2) Uani 1 1 d . . . . .
H12 H 0.4708 0.2672 0.4343 0.018 Uiso 1 1 calc R U . . .
C7 C 0.35967(13) 0.10154(11) 0.39176(10) 0.0139(2) Uani 1 1 d . . . . .
H7 H 0.4152 0.0683 0.3182 0.017 Uiso 1 1 calc R U . . .
C20 C 0.68409(13) 0.89091(12) 0.09366(10) 0.0159(2) Uani 1 1 d . . . . .
H20 H 0.7510 0.8337 0.1239 0.019 Uiso 1 1 calc R U . . .
C19 C 0.94852(12) 0.06269(10) 0.52549(10) 0.0134(2) Uani 1 1 d . . . . .
C21 C 0.62194(13) 0.84844(11) 0.04522(10) 0.0138(2) Uani 1 1 d . . . . .
C17 C 1.05282(13) 0.15204(11) 0.35933(11) 0.0158(2) Uani 1 1 d . . . . .
H17 H 1.0550 0.2225 0.3211 0.019 Uiso 1 1 calc R U . . .
C23 C 0.45179(13) 0.89296(12) -0.05279(10) 0.0160(2) Uani 1 1 d . . . . .
H23 H 0.4750 0.8071 -0.0556 0.019 Uiso 1 1 calc R U . . .
C8 C 0.28321(12) 0.23270(11) 0.41655(10) 0.0138(2) Uani 1 1 d . . . . .
C9 C 0.19989(13) 0.28411(11) 0.52620(10) 0.0149(2) Uani 1 1 d . . . . .
H9 H 0.1475 0.3720 0.5417 0.018 Uiso 1 1 calc R U . . .
C18 C 0.95245(12) 0.16907(10) 0.46339(10) 0.0138(2) Uani 1 1 d . . . . .
C13 C 0.59042(12) 0.45614(10) 0.30392(10) 0.0130(2) Uani 1 1 d . . . . .
C11 C 0.40731(12) 0.36028(10) 0.31210(10) 0.0132(2) Uani 1 1 d . . . . .
C6 C 0.35235(12) 0.02036(11) 0.47813(10) 0.0135(2) Uani 1 1 d . . . . .
C15 C 1.15233(13) -0.07662(11) 0.36546(10) 0.0153(2) Uani 1 1 d . . . . .
H15 H 1.2187 -0.1578 0.3314 0.018 Uiso 1 1 calc R U . . .
C10 C 0.29627(13) 0.32039(11) 0.32325(10) 0.0151(2) Uani 1 1 d . . . . .
H10A H 0.3205 0.2774 0.2531 0.018 Uiso 1 1 calc R U . . .
H10B H 0.2052 0.3959 0.3375 0.018 Uiso 1 1 calc R U . . .
C24 C 0.35397(14) 0.97840(12) -0.09733(11) 0.0176(2) Uani 1 1 d . . . . .
H24 H 0.3120 0.9497 -0.1305 0.021 Uiso 1 1 calc R U . . .
C16 C 1.15307(13) 0.02806(12) 0.30979(11) 0.0170(2) Uani 1 1 d . . . . .
H16 H 1.2203 0.0173 0.2386 0.020 Uiso 1 1 calc R U . . .
C1 C 0.50235(15) -0.16353(12) 0.35077(11) 0.0200(2) Uani 1 1 d . . . . .
H1C H 0.4433 -0.1340 0.3060 0.030 Uiso 1 1 calc R U . . .
H1D H 0.5445 -0.2548 0.3503 0.030 Uiso 1 1 calc R U . . .
H1E H 0.5757 -0.1382 0.3204 0.030 Uiso 1 1 calc R U . . .
C3 C 0.03356(14) 0.37527(12) 0.75137(11) 0.0198(2) Uani 1 1 d . . . . .
H3C H -0.0375 0.4056 0.7176 0.030 Uiso 1 1 calc R U . . .
H3D H 0.0899 0.4190 0.7237 0.030 Uiso 1 1 calc R U . . .
H3E H -0.0116 0.3912 0.8313 0.030 Uiso 1 1 calc R U . . .
C2 C 0.16456(16) -0.04288(14) 0.70988(12) 0.0237(3) Uani 1 1 d . . . . .
H2A H 0.1713 -0.0881 0.6490 0.035 Uiso 1 1 calc R U . . .
H2B H 0.0755 0.0337 0.7325 0.035 Uiso 1 1 calc R U . . .
H2C H 0.1706 -0.0957 0.7719 0.035 Uiso 1 1 calc R U . . .
C25 C 0.20025(18) 0.78705(15) 0.09470(14) 0.0311(3) Uani 1 1 d . . . . .
H25A H 0.1372 0.8577 0.0655 0.047 Uiso 1 1 calc R U . . .
H25B H 0.2547 0.8132 0.1185 0.047 Uiso 1 1 calc R U . . .
H25C H 0.1460 0.7586 0.1574 0.047 Uiso 1 1 calc R U . . .
C26 C 0.02666(17) 0.72807(16) -0.11387(15) 0.0312(3) Uani 1 1 d . . . . .
H26A H 0.0882 0.7224 -0.1898 0.047 Uiso 1 1 calc R U . . .
H26B H -0.0201 0.8141 -0.0822 0.047 Uiso 1 1 calc R U . . .
H26C H -0.0430 0.7041 -0.1127 0.047 Uiso 1 1 calc R U . . .
H2 H 0.531(2) 0.5472(18) 0.1866(16) 0.026(5) Uiso 1 1 d . . . . .
H3A H 0.694(2) 0.5486(19) 0.2466(17) 0.028(5) Uiso 1 1 d . . . . .
H1A H 0.324(2) 0.4494(18) 0.1478(15) 0.024(4) Uiso 1 1 d . . . . .
H3B H 0.726(2) 0.4753(18) 0.3450(16) 0.026(5) Uiso 1 1 d . . . . .
H1B H 0.3827(19) 0.5391(18) 0.1070(16) 0.025(5) Uiso 1 1 d . . . . .
H10 H 0.241(2) 0.670(2) -0.0087(19) 0.043(6) Uiso 1 1 d . . . . .
H11 H 0.124(3) 0.569(2) -0.061(2) 0.055(7) Uiso 1 1 d . . . . .
H4 H 0.619(2) 0.3481(18) 0.4298(16) 0.028(5) Uiso 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
S01 O8 1.4612(9) . ?
S01 O7 1.4694(10) . ?
S01 O9 1.4535(10) . ?
S01 C21 1.7761(12) . ?
S02 O6 1.4761(9) . ?
S02 O4 1.4428(10) . ?
S02 O5 1.4612(10) . ?
S02 C18 1.7852(12) . ?
O2 C5 1.3791(14) . ?
O2 C2 1.4245(15) . ?
O1 C6 1.3660(14) . ?
O1 C1 1.4233(16) . ?
O3 C4 1.3629(15) . ?
O3 C3 1.4330(15) . ?
O10 C25 1.4239(19) . ?
O10 H10 0.81(2) . ?
N2 C14 1.3650(15) . ?
N2 C13 1.3516(15) . ?
N2 H2 0.849(19) . ?
O11 C26 1.4218(19) . ?
O11 H11 0.85(3) . ?
N1 C14 1.3077(15) . ?
N1 H1A 0.846(19) . ?
N1 H1B 0.869(19) . ?
N4 C12 1.3745(15) . ?
N4 C13 1.3389(15) . ?
N4 H4 0.938(19) . ?
N3 C13 1.3192(15) . ?
N3 H3A 0.87(2) . ?
N3 H3B 0.883(19) . ?
C5 C4 1.3990(16) . ?
C5 C6 1.3940(17) . ?
C14 C11 1.4321(16) . ?
C4 C9 1.3973(16) . ?
C22 C22 1.427(2) 2_675 ?
C22 C21 1.4328(16) . ?
C22 C23 1.4244(16) . ?
C12 H12 0.9300 . ?
C12 C11 1.3502(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.3900(16) . ?
C7 C6 1.3932(16) . ?
C20 H20 0.9300 . ?
C20 C21 1.3718(16) . ?
C20 C24 1.4084(17) 2_675 ?
C19 C19 1.432(2) 2_756 ?
C19 C18 1.4309(16) . ?
C19 C15 1.4196(17) 2_756 ?
C17 H17 0.9300 . ?
C17 C18 1.3673(18) . ?
C17 C16 1.4097(17) . ?
C23 H23 0.9300 . ?
C23 C24 1.3685(17) . ?
C8 C9 1.3909(17) . ?
C8 C10 1.5120(16) . ?
C9 H9 0.9300 . ?
C11 C10 1.5105(16) . ?
C15 C19 1.4196(17) 2_756 ?
C15 H15 0.9300 . ?
C15 C16 1.3691(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C24 C20 1.4084(17) 2_675 ?
C24 H24 0.9300 . ?
C16 H16 0.9300 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C3 H3C 0.9600 . ?
C3 H3D 0.9600 . ?
C3 H3E 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 S01 O7 111.41(6) . . ?
O8 S01 C21 106.60(5) . . ?
O7 S01 C21 106.25(6) . . ?
O9 S01 O8 112.90(6) . . ?
O9 S01 O7 112.55(6) . . ?
O9 S01 C21 106.59(6) . . ?
O6 S02 C18 105.38(5) . . ?
O4 S02 O6 112.10(6) . . ?
O4 S02 O5 114.56(6) . . ?
O4 S02 C18 107.69(5) . . ?
O5 S02 O6 110.65(5) . . ?
O5 S02 C18 105.79(6) . . ?
C5 O2 C2 113.26(9) . . ?
C6 O1 C1 116.84(9) . . ?
C4 O3 C3 116.84(10) . . ?
C25 O10 H10 104.7(16) . . ?
C14 N2 H2 119.6(12) . . ?
C13 N2 C14 123.13(10) . . ?
C13 N2 H2 117.1(12) . . ?
C26 O11 H11 109.5(17) . . ?
C14 N1 H1A 119.2(12) . . ?
C14 N1 H1B 122.7(12) . . ?
H1A N1 H1B 118.1(17) . . ?
C12 N4 H4 119.9(12) . . ?
C13 N4 C12 120.83(10) . . ?
C13 N4 H4 119.0(12) . . ?
C13 N3 H3A 118.4(13) . . ?
C13 N3 H3B 120.4(12) . . ?
H3A N3 H3B 119.3(17) . . ?
O2 C5 C4 120.34(11) . . ?
O2 C5 C6 119.75(10) . . ?
C6 C5 C4 119.83(10) . . ?
N2 C14 C11 118.43(10) . . ?
N1 C14 N2 118.54(10) . . ?
N1 C14 C11 123.03(11) . . ?
O3 C4 C5 115.11(10) . . ?
O3 C4 C9 124.83(10) . . ?
C9 C4 C5 120.04(11) . . ?
C22 C22 C21 117.90(13) 2_675 . ?
C23 C22 C22 119.14(13) . 2_675 ?
C23 C22 C21 122.96(10) . . ?
N4 C12 H12 118.7 . . ?
C11 C12 N4 122.61(11) . . ?
C11 C12 H12 118.7 . . ?
C8 C7 H7 120.3 . . ?
C8 C7 C6 119.43(11) . . ?
C6 C7 H7 120.3 . . ?
C21 C20 H20 120.2 . . ?
C21 C20 C24 119.65(11) . 2_675 ?
C24 C20 H20 120.2 2_675 . ?
C18 C19 C19 117.96(14) . 2_756 ?
C15 C19 C19 119.18(13) 2_756 2_756 ?
C15 C19 C18 122.86(10) 2_756 . ?
C22 C21 S01 120.50(8) . . ?
C20 C21 S01 117.87(9) . . ?
C20 C21 C22 121.61(11) . . ?
C18 C17 H17 119.9 . . ?
C18 C17 C16 120.21(11) . . ?
C16 C17 H17 119.9 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.74(11) . . ?
C24 C23 H23 119.6 . . ?
C7 C8 C9 121.04(11) . . ?
C7 C8 C10 119.25(11) . . ?
C9 C8 C10 119.65(10) . . ?
C4 C9 H9 120.3 . . ?
C8 C9 C4 119.33(10) . . ?
C8 C9 H9 120.3 . . ?
C19 C18 S02 120.74(9) . . ?
C17 C18 S02 117.97(9) . . ?
C17 C18 C19 121.25(11) . . ?
N4 C13 N2 118.34(10) . . ?
N3 C13 N2 120.55(11) . . ?
N3 C13 N4 121.11(11) . . ?
C14 C11 C10 120.27(10) . . ?
C12 C11 C14 116.53(10) . . ?
C12 C11 C10 123.08(10) . . ?
O1 C6 C5 115.47(10) . . ?
O1 C6 C7 124.27(11) . . ?
C7 C6 C5 120.26(10) . . ?
C19 C15 H15 119.6 2_756 . ?
C16 C15 C19 120.77(11) . 2_756 ?
C16 C15 H15 119.6 . . ?
C8 C10 H10A 109.1 . . ?
C8 C10 H10B 109.1 . . ?
C11 C10 C8 112.60(9) . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C20 C24 H24 119.5 2_675 . ?
C23 C24 C20 120.96(11) . 2_675 ?
C23 C24 H24 119.5 . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.60(12) . . ?
C15 C16 H16 119.7 . . ?
O1 C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
O3 C3 H3C 109.5 . . ?
O3 C3 H3D 109.5 . . ?
O3 C3 H3E 109.5 . . ?
H3C C3 H3D 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O10 C25 H25A 109.5 . . ?
O10 C25 H25B 109.5 . . ?
O10 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O11 C26 H26A 109.5 . . ?
O11 C26 H26B 109.5 . . ?
O11 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C5 C4 O3 -2.99(16) . . . . ?
O2 C5 C4 C9 175.29(10) . . . . ?
O2 C5 C6 O1 6.58(16) . . . . ?
O2 C5 C6 C7 -173.67(10) . . . . ?
O3 C4 C9 C8 177.22(11) . . . . ?
O6 S02 C18 C19 -57.82(10) . . . . ?
O6 S02 C18 C17 119.97(10) . . . . ?
O8 S01 C21 C22 -174.15(10) . . . . ?
O8 S01 C21 C20 7.49(12) . . . . ?
O4 S02 C18 C19 62.01(11) . . . . ?
O4 S02 C18 C17 -120.20(10) . . . . ?
O7 S01 C21 C22 -55.22(11) . . . . ?
O7 S01 C21 C20 126.41(10) . . . . ?
O5 S02 C18 C19 -175.07(9) . . . . ?
O5 S02 C18 C17 2.72(11) . . . . ?
O9 S01 C21 C22 65.03(11) . . . . ?
O9 S01 C21 C20 -113.34(10) . . . . ?
N2 C14 C11 C12 -3.16(16) . . . . ?
N2 C14 C11 C10 172.80(11) . . . . ?
N1 C14 C11 C12 176.46(11) . . . . ?
N1 C14 C11 C10 -7.58(17) . . . . ?
N4 C12 C11 C14 1.81(17) . . . . ?
N4 C12 C11 C10 -174.03(11) . . . . ?
C5 C4 C9 C8 -0.88(17) . . . . ?
C14 N2 C13 N4 1.89(17) . . . . ?
C14 N2 C13 N3 -179.07(11) . . . . ?
C14 C11 C10 C8 -178.22(10) . . . . ?
C4 C5 C6 O1 -176.84(10) . . . . ?
C4 C5 C6 C7 2.91(17) . . . . ?
C22 C22 C21 S01 -178.21(12) 2_675 . . . ?
C22 C22 C21 C20 0.1(2) 2_675 . . . ?
C22 C22 C23 C24 0.3(2) 2_675 . . . ?
C22 C23 C24 C20 -0.5(2) . . . 2_675 ?
C12 N4 C13 N2 -3.34(17) . . . . ?
C12 N4 C13 N3 177.62(11) . . . . ?
C12 C11 C10 C8 -2.53(17) . . . . ?
C7 C8 C9 C4 1.43(17) . . . . ?
C7 C8 C10 C11 -94.12(13) . . . . ?
C19 C19 C18 S02 176.58(11) 2_756 . . . ?
C19 C19 C18 C17 -1.14(19) 2_756 . . . ?
C19 C15 C16 C17 -0.52(18) 2_756 . . . ?
C21 C22 C23 C24 -179.73(12) . . . . ?
C23 C22 C21 S01 1.86(17) . . . . ?
C23 C22 C21 C20 -179.83(12) . . . . ?
C8 C7 C6 O1 177.36(11) . . . . ?
C8 C7 C6 C5 -2.37(17) . . . . ?
C9 C8 C10 C11 83.19(14) . . . . ?
C18 C17 C16 C15 -0.72(18) . . . . ?
C13 N2 C14 N1 -178.24(11) . . . . ?
C13 N2 C14 C11 1.40(17) . . . . ?
C13 N4 C12 C11 1.48(18) . . . . ?
C6 C5 C4 O3 -179.55(10) . . . . ?
C6 C5 C4 C9 -1.27(17) . . . . ?
C6 C7 C8 C9 0.19(17) . . . . ?
C6 C7 C8 C10 177.46(10) . . . . ?
C15 C19 C18 S02 -3.51(15) 2_756 . . . ?
C15 C19 C18 C17 178.77(11) 2_756 . . . ?
C10 C8 C9 C4 -175.83(10) . . . . ?
C24 C20 C21 S01 178.35(10) 2_675 . . . ?
C24 C20 C21 C22 0.01(19) 2_675 . . . ?
C16 C17 C18 S02 -176.22(9) . . . . ?
C16 C17 C18 C19 1.56(17) . . . . ?
C1 O1 C6 C5 -178.89(11) . . . . ?
C1 O1 C6 C7 1.37(17) . . . . ?
C3 O3 C4 C5 -175.37(10) . . . . ?
C3 O3 C4 C9 6.45(17) . . . . ?
C2 O2 C5 C4 88.02(13) . . . . ?
C2 O2 C5 C6 -95.42(13) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.721
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
