# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_60221a
_database_code_depnum_ccdc_archive 'CCDC 1873203'
loop_
_audit_author_name
_audit_author_address
'Xiang Hao'
;Institutute of Chemistry Chinese Academy of Sciences
China
;
_audit_update_record             
;
2018-10-15 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H48 N4 O12'
_chemical_formula_weight         824.86

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.4005(15)
_cell_length_b                   17.879(3)
_cell_length_c                   22.883(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.991(3)
_cell_angle_gamma                90.00
_cell_volume                     4232.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4328
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      24.06

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.687748
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            23450
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         26.41
_reflns_number_total             8621
_reflns_number_gt                4639
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+1.7116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8621
_refine_ls_number_parameters     547
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26527(17) 0.72256(12) 0.11290(10) 0.0540(6) Uani 1 1 d . . .
O2 O 0.42695(19) 0.80058(13) 0.14219(10) 0.0569(6) Uani 1 1 d . . .
O3 O 0.57855(16) 0.79783(10) 0.04610(8) 0.0363(5) Uani 1 1 d . . .
O4 O 0.9083(2) 0.80846(19) 0.20959(10) 0.0933(10) Uani 1 1 d . . .
O5 O 1.1515(2) 0.82054(12) -0.00387(10) 0.0584(6) Uani 1 1 d . . .
O6 O 0.90365(18) 0.90261(10) -0.06510(7) 0.0389(5) Uani 1 1 d . . .
O7 O 0.8677(3) 1.00710(13) -0.15148(10) 0.0779(8) Uani 1 1 d . . .
O8 O 0.8905(3) 0.96606(14) -0.24096(9) 0.0783(8) Uani 1 1 d . . .
O9 O 0.95161(19) 0.64952(11) -0.13112(8) 0.0464(5) Uani 1 1 d . . .
O10 O 1.23866(19) 0.58240(11) -0.11026(9) 0.0511(5) Uani 1 1 d . . .
O11 O 1.1271(3) 0.57953(19) 0.14600(12) 0.1102(12) Uani 1 1 d . . .
O12 O 0.72025(17) 0.54348(10) 0.01790(9) 0.0440(5) Uani 1 1 d . . .
N1 N 0.7248(2) 0.82494(14) 0.14843(9) 0.0419(6) Uani 1 1 d . . .
H1 H 0.6419 0.8255 0.1470 0.050 Uiso 1 1 calc R . .
N2 N 1.0697(2) 0.92142(12) 0.03792(9) 0.0362(5) Uani 1 1 d . . .
H2 H 1.0843 0.9661 0.0509 0.043 Uiso 1 1 calc R . .
N3 N 1.1748(2) 0.66902(13) -0.04772(11) 0.0433(6) Uani 1 1 d . . .
H3 H 1.1926 0.7119 -0.0319 0.052 Uiso 1 1 calc R . .
N4 N 0.9329(2) 0.54774(13) 0.09892(10) 0.0436(6) Uani 1 1 d . . .
H4 H 0.8602 0.5272 0.1040 0.052 Uiso 1 1 calc R . .
C1 C 0.5710(2) 0.72097(15) 0.05516(11) 0.0330(6) Uani 1 1 d . . .
C2 C 0.6580(2) 0.67239(15) 0.03320(11) 0.0344(6) Uani 1 1 d . . .
H2A H 0.7280 0.6906 0.0153 0.041 Uiso 1 1 calc R . .
C3 C 0.6386(2) 0.59635(16) 0.03849(12) 0.0359(7) Uani 1 1 d . . .
C4 C 0.5326(3) 0.56822(16) 0.06375(13) 0.0439(7) Uani 1 1 d . . .
H4A H 0.5194 0.5169 0.0660 0.053 Uiso 1 1 calc R . .
C5 C 0.4476(3) 0.61769(17) 0.08541(13) 0.0448(7) Uani 1 1 d . . .
H5 H 0.3761 0.5993 0.1020 0.054 Uiso 1 1 calc R . .
C6 C 0.4666(2) 0.69494(16) 0.08289(12) 0.0361(7) Uani 1 1 d . . .
C7 C 0.3862(3) 0.74600(17) 0.11512(13) 0.0400(7) Uani 1 1 d . . .
C8 C 0.1780(3) 0.7638(2) 0.14652(16) 0.0652(10) Uani 1 1 d . . .
H8A H 0.1954 0.7513 0.1874 0.098 Uiso 1 1 calc R . .
H8B H 0.0903 0.7508 0.1330 0.098 Uiso 1 1 calc R . .
H8C H 0.1904 0.8165 0.1414 0.098 Uiso 1 1 calc R . .
C9 C 0.7019(2) 0.82832(14) 0.04327(12) 0.0315(6) Uani 1 1 d . . .
C10 C 0.7776(2) 0.84262(15) 0.09593(11) 0.0336(6) Uani 1 1 d . . .
C11 C 0.8994(2) 0.87373(15) 0.09311(11) 0.0354(6) Uani 1 1 d . . .
H11 H 0.9519 0.8836 0.1277 0.042 Uiso 1 1 calc R . .
C12 C 0.9438(2) 0.89030(14) 0.03955(11) 0.0326(6) Uani 1 1 d . . .
C13 C 0.8636(3) 0.87841(14) -0.01205(11) 0.0326(6) Uani 1 1 d . . .
C14 C 0.7420(3) 0.84768(14) -0.01000(12) 0.0338(6) Uani 1 1 d . . .
H14 H 0.6878 0.8402 -0.0445 0.041 Uiso 1 1 calc R . .
C15 C 0.7902(3) 0.8071(2) 0.20109(13) 0.0576(9) Uani 1 1 d . . .
C16 C 0.7062(3) 0.7838(2) 0.24792(14) 0.0660(10) Uani 1 1 d . . .
H16A H 0.6161 0.7876 0.2324 0.079 Uiso 1 1 calc R . .
H16B H 0.7207 0.8176 0.2811 0.079 Uiso 1 1 calc R . .
C17 C 0.7346(3) 0.7044(2) 0.26858(16) 0.0757(12) Uani 1 1 d . . .
H17A H 0.8259 0.7001 0.2819 0.091 Uiso 1 1 calc R . .
H17B H 0.6866 0.6939 0.3018 0.091 Uiso 1 1 calc R . .
C18 C 0.6997(4) 0.6470(3) 0.2212(2) 0.1005(15) Uani 1 1 d . . .
H18A H 0.6109 0.6534 0.2058 0.151 Uiso 1 1 calc R . .
H18B H 0.7118 0.5977 0.2375 0.151 Uiso 1 1 calc R . .
H18C H 0.7541 0.6535 0.1902 0.151 Uiso 1 1 calc R . .
C19 C 1.1668(3) 0.88322(17) 0.01673(12) 0.0407(7) Uani 1 1 d . . .
C20 C 1.2949(3) 0.92363(18) 0.01997(15) 0.0539(8) Uani 1 1 d . . .
H20A H 1.2811 0.9765 0.0263 0.065 Uiso 1 1 calc R . .
H20B H 1.3513 0.9048 0.0532 0.065 Uiso 1 1 calc R . .
C21 C 1.3597(4) 0.9134(3) -0.0356(2) 0.0912(14) Uani 1 1 d . . .
H21A H 1.4408 0.9406 -0.0315 0.109 Uiso 1 1 calc R . .
H21B H 1.3799 0.8608 -0.0396 0.109 Uiso 1 1 calc R . .
C22 C 1.2831(6) 0.9384(3) -0.0898(2) 0.136(2) Uani 1 1 d . . .
H22A H 1.1994 0.9151 -0.0927 0.205 Uiso 1 1 calc R . .
H22B H 1.3266 0.9246 -0.1232 0.205 Uiso 1 1 calc R . .
H22C H 1.2732 0.9917 -0.0889 0.205 Uiso 1 1 calc R . .
C23 C 0.9042(2) 0.85076(16) -0.10985(11) 0.0340(6) Uani 1 1 d . . .
C24 C 0.9234(2) 0.77586(16) -0.09680(12) 0.0374(7) Uani 1 1 d . . .
H24 H 0.9337 0.7601 -0.0579 0.045 Uiso 1 1 calc R . .
C25 C 0.9273(2) 0.72455(16) -0.14137(12) 0.0376(7) Uani 1 1 d . . .
C26 C 0.9065(3) 0.74657(18) -0.19962(12) 0.0440(7) Uani 1 1 d . . .
H26 H 0.9037 0.7114 -0.2297 0.053 Uiso 1 1 calc R . .
C27 C 0.8901(3) 0.82083(19) -0.21223(12) 0.0479(8) Uani 1 1 d . . .
H27 H 0.8779 0.8357 -0.2514 0.057 Uiso 1 1 calc R . .
C28 C 0.8910(3) 0.87572(16) -0.16805(12) 0.0387(7) Uani 1 1 d . . .
C29 C 0.8815(3) 0.9559(2) -0.18400(13) 0.0521(8) Uani 1 1 d . . .
C30 C 0.8798(6) 1.0417(2) -0.26283(17) 0.1139(18) Uani 1 1 d . . .
H30A H 0.8088 1.0662 -0.2471 0.171 Uiso 1 1 calc R . .
H30B H 0.8649 1.0409 -0.3049 0.171 Uiso 1 1 calc R . .
H30C H 0.9584 1.0682 -0.2510 0.171 Uiso 1 1 calc R . .
C31 C 0.9528(3) 0.62456(15) -0.07312(12) 0.0383(7) Uani 1 1 d . . .
C32 C 1.0609(3) 0.63160(15) -0.03264(13) 0.0371(7) Uani 1 1 d . . .
C33 C 1.0566(3) 0.60676(15) 0.02452(13) 0.0387(7) Uani 1 1 d . . .
H33 H 1.1297 0.6112 0.0514 0.046 Uiso 1 1 calc R . .
C34 C 0.9445(3) 0.57525(14) 0.04234(12) 0.0358(7) Uani 1 1 d . . .
C35 C 0.8366(2) 0.57114(14) 0.00067(13) 0.0367(7) Uani 1 1 d . . .
C36 C 0.8408(3) 0.59323(15) -0.05632(13) 0.0383(7) Uani 1 1 d . . .
H36 H 0.7687 0.5872 -0.0836 0.046 Uiso 1 1 calc R . .
C37 C 1.2558(2) 0.64215(16) -0.08477(12) 0.0355(6) Uani 1 1 d . . .
C38 C 1.3689(3) 0.69265(17) -0.09255(13) 0.0437(7) Uani 1 1 d . . .
H38A H 1.4103 0.7062 -0.0540 0.052 Uiso 1 1 calc R . .
H38B H 1.3366 0.7383 -0.1118 0.052 Uiso 1 1 calc R . .
C39 C 1.4693(3) 0.65890(18) -0.12785(14) 0.0531(8) Uani 1 1 d . . .
H39A H 1.5091 0.6166 -0.1065 0.064 Uiso 1 1 calc R . .
H39B H 1.4268 0.6404 -0.1648 0.064 Uiso 1 1 calc R . .
C40 C 1.5735(3) 0.7136(2) -0.14046(16) 0.0672(10) Uani 1 1 d . . .
H40A H 1.5347 0.7561 -0.1610 0.101 Uiso 1 1 calc R . .
H40B H 1.6323 0.6898 -0.1642 0.101 Uiso 1 1 calc R . .
H40C H 1.6197 0.7298 -0.1041 0.101 Uiso 1 1 calc R . .
C41 C 1.0220(3) 0.54946(19) 0.14674(15) 0.0581(9) Uani 1 1 d . . .
C42 C 0.9848(4) 0.5097(2) 0.19996(14) 0.0638(10) Uani 1 1 d . . .
H42A H 1.0141 0.4583 0.1987 0.077 Uiso 1 1 calc R . .
H42B H 0.8912 0.5088 0.1982 0.077 Uiso 1 1 calc R . .
C43 C 1.0378(4) 0.5434(3) 0.25741(17) 0.0977(15) Uani 1 1 d . . .
H43A H 0.9943 0.5905 0.2627 0.117 Uiso 1 1 calc R . .
H43B H 1.1290 0.5539 0.2562 0.117 Uiso 1 1 calc R . .
C44 C 1.0219(5) 0.4934(4) 0.3092(2) 0.135(2) Uani 1 1 d U . .
H44A H 0.9322 0.4811 0.3098 0.203 Uiso 1 1 calc R . .
H44B H 1.0524 0.5189 0.3449 0.203 Uiso 1 1 calc R . .
H44C H 1.0709 0.4484 0.3060 0.203 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.322(3) . ?
O1 C8 1.451(3) . ?
O2 C7 1.209(3) . ?
O3 C1 1.393(3) . ?
O3 C9 1.401(3) . ?
O4 C15 1.223(3) . ?
O5 C19 1.220(3) . ?
O6 C23 1.382(3) . ?
O6 C13 1.393(3) . ?
O7 C29 1.198(4) . ?
O8 C29 1.329(4) . ?
O8 C30 1.442(4) . ?
O9 C25 1.381(3) . ?
O9 C31 1.399(3) . ?
O10 C37 1.221(3) . ?
O11 C41 1.220(4) . ?
O12 C3 1.386(3) . ?
O12 C35 1.402(3) . ?
N1 C15 1.359(4) . ?
N1 C10 1.408(3) . ?
N1 H1 0.8600 . ?
N2 C19 1.350(3) . ?
N2 C12 1.427(3) . ?
N2 H2 0.8600 . ?
N3 C37 1.345(3) . ?
N3 C32 1.434(3) . ?
N3 H3 0.8600 . ?
N4 C41 1.359(4) . ?
N4 C34 1.402(3) . ?
N4 H4 0.8600 . ?
C1 C2 1.386(4) . ?
C1 C6 1.394(4) . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.391(4) . ?
C4 C5 1.379(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.397(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.485(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.373(4) . ?
C9 C10 1.393(3) . ?
C10 C11 1.391(4) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C13 C14 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.510(4) . ?
C16 C17 1.515(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.509(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.511(4) . ?
C20 C21 1.511(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.472(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.382(4) . ?
C23 C28 1.398(4) . ?
C24 C25 1.376(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(4) . ?
C26 C27 1.366(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.408(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.480(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C36 1.383(4) . ?
C31 C32 1.385(4) . ?
C32 C33 1.386(4) . ?
C33 C34 1.393(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.397(4) . ?
C35 C36 1.368(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.508(4) . ?
C38 C39 1.511(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.510(4) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.496(4) . ?
C42 C43 1.498(5) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.507(6) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 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
C7 O1 C8 117.7(2) . . ?
C1 O3 C9 117.17(19) . . ?
C23 O6 C13 117.5(2) . . ?
C29 O8 C30 117.2(3) . . ?
C25 O9 C31 117.0(2) . . ?
C3 O12 C35 115.7(2) . . ?
C15 N1 C10 127.3(2) . . ?
C15 N1 H1 116.4 . . ?
C10 N1 H1 116.4 . . ?
C19 N2 C12 122.3(2) . . ?
C19 N2 H2 118.8 . . ?
C12 N2 H2 118.8 . . ?
C37 N3 C32 125.0(2) . . ?
C37 N3 H3 117.5 . . ?
C32 N3 H3 117.5 . . ?
C41 N4 C34 128.2(3) . . ?
C41 N4 H4 115.9 . . ?
C34 N4 H4 115.9 . . ?
C2 C1 O3 121.0(2) . . ?
C2 C1 C6 121.7(3) . . ?
O3 C1 C6 117.1(2) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 O12 122.8(2) . . ?
C2 C3 C4 121.4(3) . . ?
O12 C3 C4 115.8(2) . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 C7 121.8(3) . . ?
C5 C6 C7 119.8(3) . . ?
O2 C7 O1 123.9(3) . . ?
O2 C7 C6 124.4(3) . . ?
O1 C7 C6 111.7(3) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 121.7(2) . . ?
C14 C9 O3 120.2(2) . . ?
C10 C9 O3 118.0(2) . . ?
C11 C10 C9 118.0(2) . . ?
C11 C10 N1 124.6(2) . . ?
C9 C10 N1 117.5(2) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 N2 119.9(2) . . ?
C13 C12 N2 120.6(2) . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 O6 120.7(2) . . ?
C12 C13 O6 119.1(2) . . ?
C9 C14 C13 119.6(2) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O4 C15 N1 122.5(3) . . ?
O4 C15 C16 122.6(3) . . ?
N1 C15 C16 114.9(3) . . ?
C15 C16 C17 111.8(3) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 112.8(3) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 N2 122.1(3) . . ?
O5 C19 C20 122.5(3) . . ?
N2 C19 C20 115.4(3) . . ?
C21 C20 C19 111.7(3) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 115.0(4) . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C20 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O6 C23 C24 120.1(2) . . ?
O6 C23 C28 119.0(2) . . ?
C24 C23 C28 120.8(3) . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 O9 122.8(3) . . ?
C24 C25 C26 120.7(3) . . ?
O9 C25 C26 116.6(2) . . ?
C27 C26 C25 118.9(3) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C28 122.3(3) . . ?
C26 C27 H27 118.8 . . ?
C28 C27 H27 118.8 . . ?
C23 C28 C27 117.0(3) . . ?
C23 C28 C29 122.8(3) . . ?
C27 C28 C29 120.2(3) . . ?
O7 C29 O8 122.0(3) . . ?
O7 C29 C28 126.6(3) . . ?
O8 C29 C28 111.4(3) . . ?
O8 C30 H30A 109.5 . . ?
O8 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O8 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C36 C31 C32 119.9(3) . . ?
C36 C31 O9 117.9(2) . . ?
C32 C31 O9 122.1(2) . . ?
C31 C32 C33 119.9(3) . . ?
C31 C32 N3 120.9(3) . . ?
C33 C32 N3 119.0(2) . . ?
C32 C33 C34 121.1(3) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C33 C34 C35 117.3(3) . . ?
C33 C34 N4 124.6(2) . . ?
C35 C34 N4 118.2(2) . . ?
C36 C35 C34 122.2(3) . . ?
C36 C35 O12 118.9(2) . . ?
C34 C35 O12 118.8(3) . . ?
C35 C36 C31 119.5(3) . . ?
C35 C36 H36 120.2 . . ?
C31 C36 H36 120.2 . . ?
O10 C37 N3 122.9(3) . . ?
O10 C37 C38 122.9(3) . . ?
N3 C37 C38 114.1(2) . . ?
C37 C38 C39 114.5(2) . . ?
C37 C38 H38A 108.6 . . ?
C39 C38 H38A 108.6 . . ?
C37 C38 H38B 108.6 . . ?
C39 C38 H38B 108.6 . . ?
H38A C38 H38B 107.6 . . ?
C40 C39 C38 113.1(3) . . ?
C40 C39 H39A 109.0 . . ?
C38 C39 H39A 109.0 . . ?
C40 C39 H39B 109.0 . . ?
C38 C39 H39B 109.0 . . ?
H39A C39 H39B 107.8 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O11 C41 N4 122.4(3) . . ?
O11 C41 C42 122.0(3) . . ?
N4 C41 C42 115.6(3) . . ?
C41 C42 C43 114.9(3) . . ?
C41 C42 H42A 108.6 . . ?
C43 C42 H42A 108.6 . . ?
C41 C42 H42B 108.6 . . ?
C43 C42 H42B 108.6 . . ?
H42A C42 H42B 107.5 . . ?
C42 C43 C44 113.0(4) . . ?
C42 C43 H43A 109.0 . . ?
C44 C43 H43A 109.0 . . ?
C42 C43 H43B 109.0 . . ?
C44 C43 H43B 109.0 . . ?
H43A C43 H43B 107.8 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
C9 O3 C1 C2 -32.4(3) . . . . ?
C9 O3 C1 C6 152.6(2) . . . . ?
O3 C1 C2 C3 -173.8(2) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 O12 180.0(2) . . . . ?
C1 C2 C3 C4 1.7(4) . . . . ?
C35 O12 C3 C2 10.9(4) . . . . ?
C35 O12 C3 C4 -170.7(2) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
O12 C3 C4 C5 179.7(2) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C2 C1 C6 C5 -3.3(4) . . . . ?
O3 C1 C6 C5 171.6(2) . . . . ?
C2 C1 C6 C7 169.6(2) . . . . ?
O3 C1 C6 C7 -15.5(4) . . . . ?
C4 C5 C6 C1 3.1(4) . . . . ?
C4 C5 C6 C7 -169.9(3) . . . . ?
C8 O1 C7 O2 -1.9(4) . . . . ?
C8 O1 C7 C6 175.1(3) . . . . ?
C1 C6 C7 O2 -33.9(4) . . . . ?
C5 C6 C7 O2 138.9(3) . . . . ?
C1 C6 C7 O1 149.1(2) . . . . ?
C5 C6 C7 O1 -38.2(4) . . . . ?
C1 O3 C9 C14 103.4(3) . . . . ?
C1 O3 C9 C10 -80.7(3) . . . . ?
C14 C9 C10 C11 -3.4(4) . . . . ?
O3 C9 C10 C11 -179.2(2) . . . . ?
C14 C9 C10 N1 176.2(2) . . . . ?
O3 C9 C10 N1 0.3(4) . . . . ?
C15 N1 C10 C11 -27.2(5) . . . . ?
C15 N1 C10 C9 153.2(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
N1 C10 C11 C12 -179.3(3) . . . . ?
C10 C11 C12 C13 2.5(4) . . . . ?
C10 C11 C12 N2 -179.3(2) . . . . ?
C19 N2 C12 C11 111.9(3) . . . . ?
C19 N2 C12 C13 -69.9(3) . . . . ?
C11 C12 C13 C14 -2.3(4) . . . . ?
N2 C12 C13 C14 179.5(2) . . . . ?
C11 C12 C13 O6 173.2(2) . . . . ?
N2 C12 C13 O6 -5.0(4) . . . . ?
C23 O6 C13 C14 -58.1(3) . . . . ?
C23 O6 C13 C12 126.4(3) . . . . ?
C10 C9 C14 C13 3.7(4) . . . . ?
O3 C9 C14 C13 179.4(2) . . . . ?
C12 C13 C14 C9 -0.7(4) . . . . ?
O6 C13 C14 C9 -176.2(2) . . . . ?
C10 N1 C15 O4 4.2(6) . . . . ?
C10 N1 C15 C16 -174.5(3) . . . . ?
O4 C15 C16 C17 -60.1(5) . . . . ?
N1 C15 C16 C17 118.7(3) . . . . ?
C15 C16 C17 C18 -65.7(4) . . . . ?
C12 N2 C19 O5 2.2(4) . . . . ?
C12 N2 C19 C20 -178.2(2) . . . . ?
O5 C19 C20 C21 41.9(4) . . . . ?
N2 C19 C20 C21 -137.7(3) . . . . ?
C19 C20 C21 C22 57.8(5) . . . . ?
C13 O6 C23 C24 -28.9(3) . . . . ?
C13 O6 C23 C28 154.1(2) . . . . ?
O6 C23 C24 C25 -178.3(2) . . . . ?
C28 C23 C24 C25 -1.3(4) . . . . ?
C23 C24 C25 O9 177.2(2) . . . . ?
C23 C24 C25 C26 -2.8(4) . . . . ?
C31 O9 C25 C24 9.6(4) . . . . ?
C31 O9 C25 C26 -170.4(2) . . . . ?
C24 C25 C26 C27 4.1(4) . . . . ?
O9 C25 C26 C27 -175.9(3) . . . . ?
C25 C26 C27 C28 -1.3(4) . . . . ?
O6 C23 C28 C27 -179.1(2) . . . . ?
C24 C23 C28 C27 3.9(4) . . . . ?
O6 C23 C28 C29 2.4(4) . . . . ?
C24 C23 C28 C29 -174.7(3) . . . . ?
C26 C27 C28 C23 -2.6(4) . . . . ?
C26 C27 C28 C29 176.0(3) . . . . ?
C30 O8 C29 O7 -1.5(5) . . . . ?
C30 O8 C29 C28 178.7(3) . . . . ?
C23 C28 C29 O7 -9.8(5) . . . . ?
C27 C28 C29 O7 171.6(3) . . . . ?
C23 C28 C29 O8 170.0(3) . . . . ?
C27 C28 C29 O8 -8.5(4) . . . . ?
C25 O9 C31 C36 96.1(3) . . . . ?
C25 O9 C31 C32 -82.8(3) . . . . ?
C36 C31 C32 C33 0.4(4) . . . . ?
O9 C31 C32 C33 179.2(2) . . . . ?
C36 C31 C32 N3 -175.2(2) . . . . ?
O9 C31 C32 N3 3.6(4) . . . . ?
C37 N3 C32 C31 -70.8(4) . . . . ?
C37 N3 C32 C33 113.5(3) . . . . ?
C31 C32 C33 C34 -0.6(4) . . . . ?
N3 C32 C33 C34 175.1(2) . . . . ?
C32 C33 C34 C35 -1.2(4) . . . . ?
C32 C33 C34 N4 178.9(2) . . . . ?
C41 N4 C34 C33 3.6(5) . . . . ?
C41 N4 C34 C35 -176.3(3) . . . . ?
C33 C34 C35 C36 3.4(4) . . . . ?
N4 C34 C35 C36 -176.8(2) . . . . ?
C33 C34 C35 O12 -176.6(2) . . . . ?
N4 C34 C35 O12 3.3(4) . . . . ?
C3 O12 C35 C36 -89.9(3) . . . . ?
C3 O12 C35 C34 90.0(3) . . . . ?
C34 C35 C36 C31 -3.6(4) . . . . ?
O12 C35 C36 C31 176.4(2) . . . . ?
C32 C31 C36 C35 1.6(4) . . . . ?
O9 C31 C36 C35 -177.2(2) . . . . ?
C32 N3 C37 O10 1.0(4) . . . . ?
C32 N3 C37 C38 -179.6(2) . . . . ?
O10 C37 C38 C39 -8.0(4) . . . . ?
N3 C37 C38 C39 172.6(3) . . . . ?
C37 C38 C39 C40 173.7(3) . . . . ?
C34 N4 C41 O11 2.8(6) . . . . ?
C34 N4 C41 C42 -175.1(3) . . . . ?
O11 C41 C42 C43 34.3(5) . . . . ?
N4 C41 C42 C43 -147.8(3) . . . . ?
C41 C42 C43 C44 -168.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_60221c
_database_code_depnum_ccdc_archive 'CCDC 1873204'
loop_
_audit_author_name
_audit_author_address
'Xiang Hao'
;Institutute of Chemistry Chinese Academy of Sciences
China
;
_audit_update_record             
;
2018-10-15 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H16 N4 O16'
_chemical_formula_weight         664.45

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.7079(11)
_cell_length_b                   14.0710(18)
_cell_length_c                   20.822(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2844.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5722
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.47

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.638505
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            15890
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.38
_reflns_number_total             5785
_reflns_number_gt                4018
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0462P)²+0.2873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(10)
_refine_ls_number_reflns         5785
_refine_ls_number_parameters     454
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.04800(18) 0.71472(13) 0.02227(9) 0.0468(5) Uani 1 1 d . . .
O2 O 1.2110(2) 0.55011(18) 0.01134(11) 0.0784(7) Uani 1 1 d . . .
O3 O 1.3972(2) 0.60122(17) 0.06199(11) 0.0714(6) Uani 1 1 d . . .
O4 O 0.9182(2) 0.75632(15) 0.24231(10) 0.0653(6) Uani 1 1 d . A .
O5 O 0.803(3) 0.9056(7) 0.2893(11) 0.127(5) Uani 0.46(3) 1 d PDU A 1
O6 O 0.692(2) 0.8744(13) 0.3809(6) 0.114(4) Uani 0.46(3) 1 d PDU A 1
O5' O 0.8506(9) 0.8918(9) 0.3202(8) 0.102(4) Uani 0.54(3) 1 d PDU A 2
O6' O 0.6496(12) 0.8939(8) 0.3584(9) 0.098(4) Uani 0.54(3) 1 d PDU A 2
O7 O 0.3403(3) 0.63913(19) 0.34311(12) 0.0846(8) Uani 1 1 d . . .
O8 O 0.4184(3) 0.4983(2) 0.32650(14) 0.0965(9) Uani 1 1 d . . .
O9 O 0.60792(19) 0.49024(13) 0.23812(8) 0.0486(5) Uani 1 1 d . A .
O10 O 0.9970(3) 0.2793(2) 0.04770(11) 0.0996(10) Uani 1 1 d . A .
O11 O 0.9112(2) 0.37393(16) -0.02564(9) 0.0662(6) Uani 1 1 d . A .
O12 O 0.68827(16) 0.48248(11) 0.01272(7) 0.0367(4) Uani 1 1 d . A .
O13 O 0.6154(3) 0.43731(17) -0.10600(10) 0.0775(7) Uani 1 1 d . . .
O14 O 0.6078(2) 0.55812(17) -0.16745(10) 0.0702(6) Uani 1 1 d . . .
O15 O 1.0020(2) 0.75718(18) -0.16962(11) 0.0752(7) Uani 1 1 d . . .
O16 O 1.1466(2) 0.75771(19) -0.09160(12) 0.0789(7) Uani 1 1 d . . .
N1 N 0.6513(2) 0.51684(17) -0.12009(9) 0.0433(5) Uani 1 1 d . . .
N2 N 1.0375(3) 0.73476(17) -0.11541(12) 0.0532(6) Uani 1 1 d . . .
N3 N 0.7396(4) 0.8539(2) 0.32821(19) 0.0846(9) Uani 1 1 d D . .
N4 N 0.4298(3) 0.5849(2) 0.32486(12) 0.0612(7) Uani 1 1 d . . .
C1 C 0.7719(2) 0.54675(16) -0.01594(11) 0.0324(5) Uani 1 1 d . . .
C2 C 0.7547(3) 0.56589(17) -0.08145(11) 0.0360(6) Uani 1 1 d . . .
C3 C 0.8402(3) 0.62964(18) -0.11153(12) 0.0404(6) Uani 1 1 d . . .
H3 H 0.8293 0.6414 -0.1552 0.048 Uiso 1 1 calc R . .
C4 C 0.9415(3) 0.67615(18) -0.07798(12) 0.0393(6) Uani 1 1 d . . .
C5 C 0.9547(2) 0.66220(17) -0.01142(12) 0.0367(6) Uani 1 1 d . . .
C6 C 0.8686(2) 0.59756(17) 0.01775(12) 0.0368(6) Uani 1 1 d . . .
H6 H 0.8762 0.5880 0.0618 0.044 Uiso 1 1 calc R . .
C7 C 1.0650(3) 0.69268(18) 0.08761(13) 0.0422(6) Uani 1 1 d . . .
C8 C 1.1775(3) 0.63767(18) 0.10521(13) 0.0430(6) Uani 1 1 d . . .
C9 C 1.2007(3) 0.6227(2) 0.17023(14) 0.0538(7) Uani 1 1 d . . .
H9 H 1.2769 0.5875 0.1831 0.065 Uiso 1 1 calc R . .
C10 C 1.1127(3) 0.6591(2) 0.21606(14) 0.0556(8) Uani 1 1 d . . .
H10 H 1.1277 0.6475 0.2595 0.067 Uiso 1 1 calc R . .
C11 C 1.0022(3) 0.7130(2) 0.19632(14) 0.0496(7) Uani 1 1 d . . .
C12 C 0.9778(3) 0.73217(19) 0.13218(14) 0.0459(7) Uani 1 1 d . . .
H12 H 0.9046 0.7706 0.1196 0.055 Uiso 1 1 calc R . .
C13 C 1.2740(3) 0.59551(19) 0.05755(14) 0.0489(7) Uani 1 1 d . . .
C14 C 1.2995(5) 0.5074(4) -0.03720(19) 0.1082(16) Uani 1 1 d . . .
H14A H 1.3482 0.5565 -0.0598 0.162 Uiso 1 1 calc R . .
H14B H 1.2442 0.4719 -0.0670 0.162 Uiso 1 1 calc R . .
H14C H 1.3644 0.4656 -0.0169 0.162 Uiso 1 1 calc R . .
C15 C 0.8004(3) 0.7114(2) 0.26052(12) 0.0479(7) Uani 1 1 d . . .
C16 C 0.7113(3) 0.7584(2) 0.30311(14) 0.0550(8) Uani 1 1 d . A .
C17 C 0.5929(3) 0.7151(2) 0.32290(13) 0.0556(8) Uani 1 1 d . . .
H17 H 0.5341 0.7468 0.3509 0.067 Uiso 1 1 calc R A .
C18 C 0.5592(3) 0.6254(2) 0.30201(12) 0.0460(7) Uani 1 1 d . A .
C19 C 0.6453(3) 0.57778(18) 0.25923(11) 0.0410(6) Uani 1 1 d . . .
C20 C 0.7659(3) 0.62179(19) 0.23957(12) 0.0453(7) Uani 1 1 d . A .
H20 H 0.8248 0.5900 0.2116 0.054 Uiso 1 1 calc R . .
C21 C 0.6800(3) 0.45280(18) 0.18547(11) 0.0383(6) Uani 1 1 d . . .
C22 C 0.7753(3) 0.38283(19) 0.19589(12) 0.0486(7) Uani 1 1 d . A .
H22 H 0.7912 0.3599 0.2371 0.058 Uiso 1 1 calc R . .
C23 C 0.8478(3) 0.34684(19) 0.14415(12) 0.0475(7) Uani 1 1 d . . .
H23 H 0.9116 0.2985 0.1507 0.057 Uiso 1 1 calc R A .
C24 C 0.8266(3) 0.38189(17) 0.08223(11) 0.0361(6) Uani 1 1 d . A .
C25 C 0.7251(2) 0.45062(16) 0.07414(10) 0.0318(5) Uani 1 1 d . . .
C26 C 0.6511(3) 0.48684(18) 0.12505(11) 0.0364(6) Uani 1 1 d . A .
H26 H 0.5837 0.5329 0.1187 0.044 Uiso 1 1 calc R . .
C27 C 0.9132(3) 0.34660(18) 0.02822(13) 0.0444(7) Uani 1 1 d . . .
C28 C 1.0882(5) 0.2391(3) 0.0005(2) 0.1161(17) Uani 1 1 d U . .
H28A H 1.0356 0.2039 -0.0304 0.174 Uiso 1 1 calc R A .
H28B H 1.1525 0.1974 0.0213 0.174 Uiso 1 1 calc R . .
H28C H 1.1375 0.2892 -0.0208 0.174 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.363(3) . ?
O1 C7 1.405(3) . ?
O2 C13 1.307(3) . ?
O2 C14 1.456(4) . ?
O3 C13 1.202(3) . ?
O4 C15 1.360(3) . ?
O4 C11 1.398(3) . ?
O5 N3 1.248(8) . ?
O6 N3 1.226(8) . ?
O5' N3 1.213(7) . ?
O6' N3 1.216(6) . ?
O7 N4 1.217(3) . ?
O8 N4 1.223(4) . ?
O9 C19 1.357(3) . ?
O9 C21 1.403(3) . ?
O10 C27 1.312(3) . ?
O10 C28 1.438(4) . ?
O11 C27 1.186(3) . ?
O12 C1 1.354(3) . ?
O12 C25 1.402(3) . ?
O13 N1 1.208(3) . ?
O14 N1 1.220(3) . ?
O15 N2 1.222(3) . ?
O16 N2 1.213(3) . ?
N1 C2 1.460(3) . ?
N2 C4 1.468(3) . ?
N3 C16 1.468(4) . ?
N4 C18 1.460(4) . ?
C1 C6 1.373(3) . ?
C1 C2 1.400(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(3) . ?
C5 C6 1.376(3) . ?
C6 H6 0.9300 . ?
C7 C12 1.374(4) . ?
C7 C8 1.388(4) . ?
C8 C9 1.389(4) . ?
C8 C13 1.488(4) . ?
C9 C10 1.380(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.376(4) . ?
C15 C16 1.404(4) . ?
C16 C17 1.365(5) . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.393(3) . ?
C19 C20 1.386(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(4) . ?
C21 C26 1.375(3) . ?
C22 C23 1.383(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.396(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.391(3) . ?
C24 C27 1.490(4) . ?
C25 C26 1.378(3) . ?
C26 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C5 O1 C7 117.16(19) . . ?
C13 O2 C14 115.9(3) . . ?
C15 O4 C11 118.6(2) . . ?
C19 O9 C21 117.4(2) . . ?
C27 O10 C28 117.0(3) . . ?
C1 O12 C25 117.56(18) . . ?
O13 N1 O14 122.5(2) . . ?
O13 N1 C2 120.2(2) . . ?
O14 N1 C2 117.3(2) . . ?
O16 N2 O15 123.7(2) . . ?
O16 N2 C4 119.1(2) . . ?
O15 N2 C4 117.2(3) . . ?
O5' N3 O6' 120.4(7) . . ?
O5' N3 O6 110.7(8) . . ?
O6' N3 O6 32.4(7) . . ?
O5' N3 O5 38.8(7) . . ?
O6' N3 O5 114.7(8) . . ?
O6 N3 O5 128.9(12) . . ?
O5' N3 C16 121.3(5) . . ?
O6' N3 C16 118.3(6) . . ?
O6 N3 C16 117.7(8) . . ?
O5 N3 C16 113.2(8) . . ?
O7 N4 O8 123.5(3) . . ?
O7 N4 C18 118.1(3) . . ?
O8 N4 C18 118.4(3) . . ?
O12 C1 C6 122.2(2) . . ?
O12 C1 C2 119.1(2) . . ?
C6 C1 C2 118.6(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 N1 118.2(2) . . ?
C1 C2 N1 121.8(2) . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 N2 116.9(2) . . ?
C5 C4 N2 123.0(2) . . ?
O1 C5 C6 122.3(2) . . ?
O1 C5 C4 119.5(2) . . ?
C6 C5 C4 118.2(2) . . ?
C1 C6 C5 122.3(2) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C12 C7 C8 122.2(2) . . ?
C12 C7 O1 119.5(2) . . ?
C8 C7 O1 118.1(2) . . ?
C7 C8 C9 118.0(3) . . ?
C7 C8 C13 122.8(2) . . ?
C9 C8 C13 119.2(2) . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 O4 119.4(3) . . ?
C12 C11 O4 118.5(3) . . ?
C7 C12 C11 117.9(3) . . ?
C7 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
O3 C13 O2 123.7(3) . . ?
O3 C13 C8 123.3(3) . . ?
O2 C13 C8 113.1(2) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C20 122.8(2) . . ?
O4 C15 C16 118.4(3) . . ?
C20 C15 C16 118.8(3) . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 N3 117.3(3) . . ?
C15 C16 N3 122.7(3) . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 N4 117.4(3) . . ?
C19 C18 N4 122.5(3) . . ?
O9 C19 C20 122.4(2) . . ?
O9 C19 C18 118.9(3) . . ?
C20 C19 C18 118.7(2) . . ?
C15 C20 C19 121.4(3) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C22 C21 C26 122.3(2) . . ?
C22 C21 O9 118.9(2) . . ?
C26 C21 O9 118.8(2) . . ?
C21 C22 C23 118.9(2) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C24 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 117.5(2) . . ?
C25 C24 C27 122.7(2) . . ?
C23 C24 C27 119.8(2) . . ?
C26 C25 C24 122.2(2) . . ?
C26 C25 O12 116.8(2) . . ?
C24 C25 O12 120.9(2) . . ?
C21 C26 C25 117.9(2) . . ?
C21 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
O11 C27 O10 122.5(3) . . ?
O11 C27 C24 126.6(3) . . ?
O10 C27 C24 110.9(2) . . ?
O10 C28 H28A 109.5 . . ?
O10 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O10 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C25 O12 C1 C6 -16.1(3) . . . . ?
C25 O12 C1 C2 167.3(2) . . . . ?
O12 C1 C2 C3 -178.9(2) . . . . ?
C6 C1 C2 C3 4.4(4) . . . . ?
O12 C1 C2 N1 -1.5(3) . . . . ?
C6 C1 C2 N1 -178.2(2) . . . . ?
O13 N1 C2 C3 148.9(3) . . . . ?
O14 N1 C2 C3 -28.6(3) . . . . ?
O13 N1 C2 C1 -28.5(4) . . . . ?
O14 N1 C2 C1 154.0(2) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
N1 C2 C3 C4 -178.4(2) . . . . ?
C2 C3 C4 C5 -3.0(4) . . . . ?
C2 C3 C4 N2 173.4(2) . . . . ?
O16 N2 C4 C3 -161.9(3) . . . . ?
O15 N2 C4 C3 17.7(4) . . . . ?
O16 N2 C4 C5 14.4(4) . . . . ?
O15 N2 C4 C5 -166.0(3) . . . . ?
C7 O1 C5 C6 7.3(3) . . . . ?
C7 O1 C5 C4 -175.0(2) . . . . ?
C3 C4 C5 O1 -174.5(2) . . . . ?
N2 C4 C5 O1 9.3(4) . . . . ?
C3 C4 C5 C6 3.4(4) . . . . ?
N2 C4 C5 C6 -172.8(2) . . . . ?
O12 C1 C6 C5 179.3(2) . . . . ?
C2 C1 C6 C5 -4.1(4) . . . . ?
O1 C5 C6 C1 178.0(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C5 O1 C7 C12 -85.0(3) . . . . ?
C5 O1 C7 C8 100.4(3) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
O1 C7 C8 C9 174.6(2) . . . . ?
C12 C7 C8 C13 -179.1(2) . . . . ?
O1 C7 C8 C13 -4.7(4) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C13 C8 C9 C10 -178.9(3) . . . . ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C9 C10 C11 O4 -175.2(3) . . . . ?
C15 O4 C11 C10 -96.1(3) . . . . ?
C15 O4 C11 C12 89.1(3) . . . . ?
C8 C7 C12 C11 -2.2(4) . . . . ?
O1 C7 C12 C11 -176.6(2) . . . . ?
C10 C11 C12 C7 2.4(4) . . . . ?
O4 C11 C12 C7 177.0(2) . . . . ?
C14 O2 C13 O3 -1.7(5) . . . . ?
C14 O2 C13 C8 179.7(3) . . . . ?
C7 C8 C13 O3 131.8(3) . . . . ?
C9 C8 C13 O3 -47.5(4) . . . . ?
C7 C8 C13 O2 -49.5(4) . . . . ?
C9 C8 C13 O2 131.1(3) . . . . ?
C11 O4 C15 C20 5.4(4) . . . . ?
C11 O4 C15 C16 -175.4(3) . . . . ?
O4 C15 C16 C17 -179.4(3) . . . . ?
C20 C15 C16 C17 -0.1(4) . . . . ?
O4 C15 C16 N3 0.6(4) . . . . ?
C20 C15 C16 N3 179.8(3) . . . . ?
O5' N3 C16 C17 169.8(12) . . . . ?
O6' N3 C16 C17 -8.9(13) . . . . ?
O6 N3 C16 C17 27.9(14) . . . . ?
O5 N3 C16 C17 -147.3(15) . . . . ?
O5' N3 C16 C15 -10.2(13) . . . . ?
O6' N3 C16 C15 171.1(12) . . . . ?
O6 N3 C16 C15 -152.0(14) . . . . ?
O5 N3 C16 C15 32.8(15) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
N3 C16 C17 C18 -179.5(3) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C16 C17 C18 N4 -179.2(3) . . . . ?
O7 N4 C18 C17 22.8(4) . . . . ?
O8 N4 C18 C17 -155.0(3) . . . . ?
O7 N4 C18 C19 -155.4(3) . . . . ?
O8 N4 C18 C19 26.8(4) . . . . ?
C21 O9 C19 C20 -12.9(3) . . . . ?
C21 O9 C19 C18 166.8(2) . . . . ?
C17 C18 C19 O9 -178.4(2) . . . . ?
N4 C18 C19 O9 -0.2(4) . . . . ?
C17 C18 C19 C20 1.4(4) . . . . ?
N4 C18 C19 C20 179.5(2) . . . . ?
O4 C15 C20 C19 179.7(2) . . . . ?
C16 C15 C20 C19 0.5(4) . . . . ?
O9 C19 C20 C15 178.6(2) . . . . ?
C18 C19 C20 C15 -1.1(4) . . . . ?
C19 O9 C21 C22 104.8(3) . . . . ?
C19 O9 C21 C26 -76.1(3) . . . . ?
C26 C21 C22 C23 1.7(4) . . . . ?
O9 C21 C22 C23 -179.1(2) . . . . ?
C21 C22 C23 C24 1.1(4) . . . . ?
C22 C23 C24 C25 -3.3(4) . . . . ?
C22 C23 C24 C27 175.6(3) . . . . ?
C23 C24 C25 C26 2.8(4) . . . . ?
C27 C24 C25 C26 -176.1(2) . . . . ?
C23 C24 C25 O12 -173.6(2) . . . . ?
C27 C24 C25 O12 7.5(4) . . . . ?
C1 O12 C25 C26 104.4(2) . . . . ?
C1 O12 C25 C24 -79.0(3) . . . . ?
C22 C21 C26 C25 -2.2(4) . . . . ?
O9 C21 C26 C25 178.6(2) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
O12 C25 C26 C21 176.4(2) . . . . ?
C28 O10 C27 O11 0.0(5) . . . . ?
C28 O10 C27 C24 -179.4(3) . . . . ?
C25 C24 C27 O11 3.2(5) . . . . ?
C23 C24 C27 O11 -175.6(3) . . . . ?
C25 C24 C27 O10 -177.4(3) . . . . ?
C23 C24 C27 O10 3.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1873320'
loop_
_audit_author_name
_audit_author_address
'Xiang Hao'
;Institutute of Chemistry Chinese Academy of Sciences
China
;
_audit_update_record             
;
2018-10-15 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H52 N4 O16'
_chemical_formula_sum            'C48 H52 N4 O16'
_chemical_formula_weight         940.94

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.710(4)
_cell_length_b                   11.844(6)
_cell_length_c                   13.132(6)
_cell_angle_alpha                94.145(9)
_cell_angle_beta                 105.695(4)
_cell_angle_gamma                103.095(9)
_cell_volume                     1257.4(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3991
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.9

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9851
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15913
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         27.86
_reflns_number_total             5959
_reflns_number_gt                3803
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'CrystalStructure 3.7.0'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0607P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.044(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5959
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.14202(10) 0.29442(7) 0.50972(6) 0.0167(2) Uani 1 1 d . . .
N1 N 0.41875(13) 0.31454(9) 0.45088(8) 0.0175(2) Uani 1 1 d . . .
H1A H 0.3621(19) 0.3665(14) 0.4454(12) 0.031(4) Uiso 1 1 d . . .
C1 C -0.07213(15) 0.13959(11) 0.38848(9) 0.0160(3) Uani 1 1 d . . .
H1 H -0.0505 0.0852 0.4368 0.019 Uiso 1 1 calc R . .
O2 O 0.28884(10) 0.01030(7) 0.73845(6) 0.0163(2) Uani 1 1 d . . .
N2 N 0.56831(13) 0.02596(9) 0.68564(9) 0.0181(2) Uani 1 1 d . . .
H2 H 0.5310(18) -0.0174(13) 0.7296(12) 0.026(4) Uiso 1 1 d . . .
C2 C -0.19690(15) 0.10467(10) 0.29301(9) 0.0146(3) Uani 1 1 d . . .
O3 O -0.50708(11) 0.08125(8) 0.11825(7) 0.0245(2) Uani 1 1 d . . .
C3 C -0.23157(15) 0.18348(11) 0.22097(9) 0.0157(3) Uani 1 1 d . . .
O4 O -0.35711(12) 0.21794(8) 0.04949(7) 0.0267(2) Uani 1 1 d . . .
C4 C -0.13686(15) 0.29852(11) 0.24849(10) 0.0181(3) Uani 1 1 d . . .
H4 H -0.1594 0.3532 0.2006 0.022 Uiso 1 1 calc R . .
O5 O 0.23555(11) 0.49337(8) 0.41327(8) 0.0259(2) Uani 1 1 d . . .
C5 C -0.01001(15) 0.33649(11) 0.34381(10) 0.0168(3) Uani 1 1 d . . .
O6 O -0.00149(11) 0.53217(8) 0.32824(8) 0.0264(2) Uani 1 1 d . . .
C6 C 0.02104(14) 0.25469(10) 0.41292(9) 0.0149(3) Uani 1 1 d . . .
O7 O 0.61623(13) 0.25600(9) 0.39326(8) 0.0338(3) Uani 1 1 d . . .
C7 C 0.20519(15) 0.14563(10) 0.61917(9) 0.0157(3) Uani 1 1 d . . .
H7 H 0.1068 0.1392 0.6391 0.019 Uiso 1 1 calc R . .
O8 O 0.79137(11) 0.08088(8) 0.62297(7) 0.0240(2) Uani 1 1 d . . .
C8 C 0.24269(15) 0.22037(10) 0.54818(10) 0.0154(3) Uani 1 1 d . . .
C9 C 0.38730(15) 0.23144(10) 0.51820(9) 0.0155(3) Uani 1 1 d . . .
C10 C 0.49543(15) 0.16437(10) 0.56047(9) 0.0166(3) Uani 1 1 d . . .
H10 H 0.5926 0.1694 0.5394 0.020 Uiso 1 1 calc R . .
C11 C 0.46132(15) 0.09002(10) 0.63359(9) 0.0157(3) Uani 1 1 d . . .
C12 C 0.31431(15) 0.08079(10) 0.66029(9) 0.0150(3) Uani 1 1 d . . .
C13 C -0.37906(16) 0.15230(11) 0.12566(10) 0.0185(3) Uani 1 1 d . . .
C14 C -0.5000(2) 0.20117(13) -0.04287(11) 0.0386(4) Uani 1 1 d . . .
H14A H -0.5357 0.1189 -0.0754 0.058 Uiso 1 1 calc R . .
H14B H -0.4713 0.2508 -0.0950 0.058 Uiso 1 1 calc R . .
H14C H -0.5896 0.2225 -0.0207 0.058 Uiso 1 1 calc R . .
C15 C 0.08949(16) 0.46006(11) 0.36739(10) 0.0183(3) Uani 1 1 d . . .
C16 C 0.08771(17) 0.65419(11) 0.34212(12) 0.0265(3) Uani 1 1 d . . .
H16A H 0.1331 0.6843 0.4185 0.040 Uiso 1 1 calc R . .
H16B H 0.0124 0.6996 0.3074 0.040 Uiso 1 1 calc R . .
H16C H 0.1779 0.6611 0.3098 0.040 Uiso 1 1 calc R . .
C17 C 0.53567(17) 0.32690(11) 0.39825(10) 0.0214(3) Uani 1 1 d . . .
C18 C 0.55654(18) 0.43507(12) 0.34348(11) 0.0255(3) Uani 1 1 d . . .
H18A H 0.5063 0.4915 0.3734 0.031 Uiso 1 1 calc R . .
H18B H 0.6757 0.4726 0.3590 0.031 Uiso 1 1 calc R . .
C19 C 0.4792(2) 0.40894(15) 0.22436(12) 0.0451(4) Uani 1 1 d . . .
H19A H 0.3578 0.3819 0.2079 0.054 Uiso 1 1 calc R . .
H19B H 0.5185 0.3454 0.1949 0.054 Uiso 1 1 calc R . .
C20 C 0.5235(3) 0.5179(2) 0.17215(16) 0.0778(7) Uani 1 1 d . . .
H20A H 0.4829 0.5803 0.2005 0.117 Uiso 1 1 calc R . .
H20B H 0.4724 0.4993 0.0947 0.117 Uiso 1 1 calc R . .
H20C H 0.6436 0.5440 0.1878 0.117 Uiso 1 1 calc R . .
C21 C 0.72249(16) 0.02510(11) 0.68027(10) 0.0190(3) Uani 1 1 d . . .
C22 C 0.80593(17) -0.04876(13) 0.75455(12) 0.0278(3) Uani 1 1 d . . .
H22A H 0.8376 -0.1080 0.7130 0.033 Uiso 1 1 calc R . .
H22B H 0.7285 -0.0904 0.7907 0.033 Uiso 1 1 calc R . .
C23 C 0.9599(2) 0.02863(16) 0.83825(13) 0.0422(4) Uani 1 1 d . . .
H23A H 1.0177 -0.0217 0.8829 0.051 Uiso 1 1 calc R . .
H23B H 1.0357 0.0711 0.8014 0.051 Uiso 1 1 calc R . .
C24 C 0.9195(3) 0.11606(18) 0.90923(14) 0.0598(6) Uani 1 1 d . . .
H24A H 0.8741 0.1719 0.8666 0.090 Uiso 1 1 calc R . .
H24B H 1.0201 0.1582 0.9655 0.090 Uiso 1 1 calc R . .
H24C H 0.8381 0.0750 0.9418 0.090 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.3827(15) . ?
O1 C8 1.4022(15) . ?
N1 C17 1.3654(18) . ?
N1 C9 1.3999(15) . ?
N1 H1A 0.868(16) . ?
C1 C2 1.3814(17) . ?
C1 C6 1.3837(18) . ?
C1 H1 0.9500 . ?
O2 C2 1.3827(15) 2_556 ?
O2 C12 1.4010(14) . ?
N2 C21 1.3661(18) . ?
N2 C11 1.4008(16) . ?
N2 H2 0.878(15) . ?
C2 O2 1.3826(15) 2_556 ?
C2 C3 1.3994(16) . ?
O3 C13 1.2105(16) . ?
C3 C4 1.3877(18) . ?
C3 C13 1.4838(18) . ?
O4 C13 1.3379(15) . ?
O4 C14 1.4478(16) . ?
C4 C5 1.3911(17) . ?
C4 H4 0.9500 . ?
O5 C15 1.2086(16) . ?
C5 C6 1.3959(17) . ?
C5 C15 1.4843(18) . ?
O6 C15 1.3309(15) . ?
O6 C16 1.4499(16) . ?
O7 C17 1.2188(16) . ?
C7 C12 1.3775(17) . ?
C7 C8 1.3828(17) . ?
C7 H7 0.9500 . ?
O8 C21 1.2244(15) . ?
C8 C9 1.3999(18) . ?
C9 C10 1.3951(17) . ?
C10 C11 1.3942(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3999(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.5134(18) . ?
C18 C19 1.504(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.526(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.5076(18) . ?
C22 C23 1.532(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.506(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C6 O1 C8 117.23(9) . . ?
C17 N1 C9 127.03(11) . . ?
C17 N1 H1A 116.5(10) . . ?
C9 N1 H1A 116.3(10) . . ?
C2 C1 C6 119.24(11) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C2 O2 C12 119.18(9) 2_556 . ?
C21 N2 C11 129.23(11) . . ?
C21 N2 H2 116.5(10) . . ?
C11 N2 H2 114.2(10) . . ?
C1 C2 O2 122.01(10) . 2_556 ?
C1 C2 C3 121.34(11) . . ?
O2 C2 C3 116.59(11) 2_556 . ?
C4 C3 C2 117.91(11) . . ?
C4 C3 C13 119.43(11) . . ?
C2 C3 C13 122.05(11) . . ?
C13 O4 C14 115.32(11) . . ?
C3 C4 C5 122.22(11) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 117.92(11) . . ?
C4 C5 C15 119.61(11) . . ?
C6 C5 C15 122.45(11) . . ?
C15 O6 C16 115.27(10) . . ?
O1 C6 C1 121.02(11) . . ?
O1 C6 C5 117.51(11) . . ?
C1 C6 C5 121.36(11) . . ?
C12 C7 C8 118.22(11) . . ?
C12 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C7 C8 C9 121.75(11) . . ?
C7 C8 O1 120.58(11) . . ?
C9 C8 O1 117.50(11) . . ?
C10 C9 N1 123.62(11) . . ?
C10 C9 C8 118.96(11) . . ?
N1 C9 C8 117.34(11) . . ?
C11 C10 C9 120.17(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 118.84(11) . . ?
C10 C11 N2 123.98(11) . . ?
C12 C11 N2 117.15(11) . . ?
C7 C12 C11 122.02(11) . . ?
C7 C12 O2 120.65(11) . . ?
C11 C12 O2 117.09(11) . . ?
O3 C13 O4 123.31(12) . . ?
O3 C13 C3 125.26(11) . . ?
O4 C13 C3 111.33(11) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 O6 122.86(12) . . ?
O5 C15 C5 125.70(12) . . ?
O6 C15 C5 111.41(11) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O7 C17 N1 123.37(12) . . ?
O7 C17 C18 121.65(12) . . ?
N1 C17 C18 114.96(12) . . ?
C19 C18 C17 112.99(12) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 110.55(15) . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O8 C21 N2 124.20(12) . . ?
O8 C21 C22 121.72(12) . . ?
N2 C21 C22 114.06(11) . . ?
C21 C22 C23 110.13(12) . . ?
C21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C22 112.50(14) . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C6 C1 C2 O2 176.70(10) . . . 2_556 ?
C6 C1 C2 C3 -0.43(18) . . . . ?
C1 C2 C3 C4 -0.23(18) . . . . ?
O2 C2 C3 C4 -177.50(10) 2_556 . . . ?
C1 C2 C3 C13 -171.25(11) . . . . ?
O2 C2 C3 C13 11.47(17) 2_556 . . . ?
C2 C3 C4 C5 0.43(18) . . . . ?
C13 C3 C4 C5 171.70(11) . . . . ?
C3 C4 C5 C6 0.03(18) . . . . ?
C3 C4 C5 C15 178.50(11) . . . . ?
C8 O1 C6 C1 41.61(15) . . . . ?
C8 O1 C6 C5 -142.12(11) . . . . ?
C2 C1 C6 O1 177.03(10) . . . . ?
C2 C1 C6 C5 0.91(18) . . . . ?
C4 C5 C6 O1 -176.96(10) . . . . ?
C15 C5 C6 O1 4.61(17) . . . . ?
C4 C5 C6 C1 -0.71(18) . . . . ?
C15 C5 C6 C1 -179.14(11) . . . . ?
C12 C7 C8 C9 -0.25(18) . . . . ?
C12 C7 C8 O1 -175.49(10) . . . . ?
C6 O1 C8 C7 -94.77(13) . . . . ?
C6 O1 C8 C9 89.79(13) . . . . ?
C17 N1 C9 C10 14.81(19) . . . . ?
C17 N1 C9 C8 -168.48(12) . . . . ?
C7 C8 C9 C10 0.60(18) . . . . ?
O1 C8 C9 C10 175.98(10) . . . . ?
C7 C8 C9 N1 -176.27(11) . . . . ?
O1 C8 C9 N1 -0.89(16) . . . . ?
N1 C9 C10 C11 174.96(11) . . . . ?
C8 C9 C10 C11 -1.70(17) . . . . ?
C9 C10 C11 C12 2.43(17) . . . . ?
C9 C10 C11 N2 -175.30(11) . . . . ?
C21 N2 C11 C10 2.6(2) . . . . ?
C21 N2 C11 C12 -175.13(12) . . . . ?
C8 C7 C12 C11 1.02(18) . . . . ?
C8 C7 C12 O2 175.23(10) . . . . ?
C10 C11 C12 C7 -2.11(18) . . . . ?
N2 C11 C12 C7 175.78(11) . . . . ?
C10 C11 C12 O2 -176.53(10) . . . . ?
N2 C11 C12 O2 1.36(16) . . . . ?
C2 O2 C12 C7 89.82(14) 2_556 . . . ?
C2 O2 C12 C11 -95.69(13) 2_556 . . . ?
C14 O4 C13 O3 1.81(18) . . . . ?
C14 O4 C13 C3 -174.67(11) . . . . ?
C4 C3 C13 O3 -143.58(13) . . . . ?
C2 C3 C13 O3 27.31(19) . . . . ?
C4 C3 C13 O4 32.82(16) . . . . ?
C2 C3 C13 O4 -156.29(11) . . . . ?
C16 O6 C15 O5 1.43(18) . . . . ?
C16 O6 C15 C5 -176.59(10) . . . . ?
C4 C5 C15 O5 -143.82(13) . . . . ?
C6 C5 C15 O5 34.58(19) . . . . ?
C4 C5 C15 O6 34.13(15) . . . . ?
C6 C5 C15 O6 -147.47(12) . . . . ?
C9 N1 C17 O7 9.4(2) . . . . ?
C9 N1 C17 C18 -171.87(12) . . . . ?
O7 C17 C18 C19 74.86(19) . . . . ?
N1 C17 C18 C19 -103.88(15) . . . . ?
C17 C18 C19 C20 -172.52(15) . . . . ?
C11 N2 C21 O8 -2.6(2) . . . . ?
C11 N2 C21 C22 175.61(12) . . . . ?
O8 C21 C22 C23 62.61(17) . . . . ?
N2 C21 C22 C23 -115.65(13) . . . . ?
C21 C22 C23 C24 62.94(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.878(15) 2.232(15) 3.0721(18) 160.1(13) 2_556
N2 H2 O2 0.878(15) 2.238(14) 2.6773(18) 110.7(11) .
N1 H1A O5 0.868(16) 2.059(16) 2.9212(18) 172.2(14) .

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.500 0.000 150.4 32.6
_platon_squeeze_details          
; 
;


_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.047
