# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

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

data_1a
_database_code_depnum_ccdc_archive 'CCDC 2078843'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H33 N3 O5'
_chemical_formula_sum            'C34 H33 N3 O5'
_chemical_formula_weight         563.63

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0138(5)
_cell_length_b                   11.7765(6)
_cell_length_c                   12.7363(6)
_cell_angle_alpha                84.6324(15)
_cell_angle_beta                 78.1330(15)
_cell_angle_gamma                84.1528(16)
_cell_volume                     1458.14(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8709
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20829
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5718
_reflns_number_gt                4094
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+0.5252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5718
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2498(2) 0.61372(16) 1.12804(15) 0.0424(5) Uani 1 1 d . . . . .
C2 C 0.2023(2) 0.58383(17) 1.23703(16) 0.0517(6) Uani 1 1 d . . . . .
H2 H 0.2609 0.5752 1.2858 0.062 Uiso 1 1 calc R U . . .
C3 C 0.0657(3) 0.56762(19) 1.26934(18) 0.0601(6) Uani 1 1 d . . . . .
H3 H 0.0311 0.5473 1.3414 0.072 Uiso 1 1 calc R U . . .
C4 C -0.0222(3) 0.58096(19) 1.19652(19) 0.0591(6) Uani 1 1 d . . . . .
H4 H -0.1144 0.5700 1.2213 0.071 Uiso 1 1 calc R U . . .
C5 C 0.0242(2) 0.61010(18) 1.08820(17) 0.0500(5) Uani 1 1 d . . . . .
H5 H -0.0353 0.6181 1.0402 0.060 Uiso 1 1 calc R U . . .
C6 C 0.1626(2) 0.62716(15) 1.05303(15) 0.0397(4) Uani 1 1 d . . . . .
C7 C 0.24553(19) 0.66170(16) 0.95080(14) 0.0369(4) Uani 1 1 d . . . . .
C8 C 0.3740(2) 0.66853(16) 0.96779(14) 0.0383(4) Uani 1 1 d . . . . .
C9 C 0.49391(19) 0.70730(16) 0.88616(14) 0.0367(4) Uani 1 1 d . . . . .
H9 H 0.5615 0.6421 0.8686 0.044 Uiso 1 1 calc R U . . .
C10 C 0.5585(2) 0.7986(2) 0.93142(16) 0.0472(5) Uani 1 1 d . . . . .
C11 C 0.7033(3) 0.8297(3) 1.0506(2) 0.0891(10) Uani 1 1 d . . . . .
H11A H 0.7959 0.7988 1.0546 0.107 Uiso 1 1 calc R U . . .
H11B H 0.7088 0.9028 1.0088 0.107 Uiso 1 1 calc R U . . .
C12 C 0.6276(4) 0.8468(3) 1.1568(2) 0.1025(11) Uani 1 1 d . . . . .
H12A H 0.5403 0.8872 1.1527 0.154 Uiso 1 1 calc R U . . .
H12B H 0.6776 0.8909 1.1928 0.154 Uiso 1 1 calc R U . . .
H12C H 0.6140 0.7740 1.1963 0.154 Uiso 1 1 calc R U . . .
C13 C 0.1076(2) 0.88918(17) 0.87942(15) 0.0417(5) Uani 1 1 d . . . . .
H13 H 0.1781 0.8957 0.9154 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0160(2) 0.98287(17) 0.86583(16) 0.0459(5) Uani 1 1 d . . . . .
H14 H 0.0270 1.0517 0.8921 0.055 Uiso 1 1 calc R U . . .
C15 C -0.0916(2) 0.97689(18) 0.81412(16) 0.0464(5) Uani 1 1 d . . . . .
C16 C -0.1920(3) 1.0793(2) 0.8018(2) 0.0714(7) Uani 1 1 d . . . . .
H16A H -0.2385 1.0695 0.7448 0.107 Uiso 1 1 calc R U . . .
H16B H -0.1439 1.1472 0.7848 0.107 Uiso 1 1 calc R U . . .
H16C H -0.2577 1.0864 0.8678 0.107 Uiso 1 1 calc R U . . .
C17 C -0.1056(2) 0.87289(19) 0.77720(17) 0.0494(5) Uani 1 1 d . . . . .
H17 H -0.1779 0.8660 0.7432 0.059 Uiso 1 1 calc R U . . .
C18 C -0.01405(19) 0.77884(18) 0.78992(15) 0.0433(5) Uani 1 1 d . . . . .
H18 H -0.0260 0.7098 0.7645 0.052 Uiso 1 1 calc R U . . .
C19 C 0.09563(18) 0.78580(16) 0.84004(14) 0.0352(4) Uani 1 1 d . . . . .
C20 C 0.20123(18) 0.68390(15) 0.84493(14) 0.0354(4) Uani 1 1 d . . . . .
H20 H 0.1575 0.6162 0.8344 0.042 Uiso 1 1 calc R U . . .
C21 C 0.38757(18) 0.56907(15) 0.72805(14) 0.0346(4) Uani 1 1 d . . . . .
C22 C 0.3990(3) 0.40425(18) 0.62207(19) 0.0617(6) Uani 1 1 d . . . . .
H22A H 0.4832 0.3834 0.6467 0.093 Uiso 1 1 calc R U . . .
H22B H 0.4131 0.3945 0.5465 0.093 Uiso 1 1 calc R U . . .
H22C H 0.3303 0.3562 0.6605 0.093 Uiso 1 1 calc R U . . .
C23 C 0.2755(2) 0.58353(19) 0.57199(16) 0.0500(5) Uani 1 1 d . . . . .
C24 C 0.1706(3) 0.7634(2) 0.5042(2) 0.0824(9) Uani 1 1 d . . . . .
H24A H 0.2353 0.7902 0.4426 0.124 Uiso 1 1 calc R U . . .
H24B H 0.1165 0.8277 0.5369 0.124 Uiso 1 1 calc R U . . .
H24C H 0.1118 0.7147 0.4821 0.124 Uiso 1 1 calc R U . . .
C25 C 0.28766(18) 0.75958(16) 0.65522(14) 0.0361(4) Uani 1 1 d . . . . .
C26 C 0.33463(18) 0.69191(15) 0.75057(13) 0.0329(4) Uani 1 1 d . . . . .
C27 C 0.44429(18) 0.75958(15) 0.78344(13) 0.0335(4) Uani 1 1 d . . . . .
H27 H 0.3976 0.8345 0.8016 0.040 Uiso 1 1 calc R U . . .
C28 C 0.56187(18) 0.78417(15) 0.68978(14) 0.0347(4) Uani 1 1 d . . . . .
C29 C 0.5670(2) 0.89379(16) 0.63881(16) 0.0441(5) Uani 1 1 d . . . . .
H29 H 0.5026 0.9519 0.6658 0.053 Uiso 1 1 calc R U . . .
C30 C 0.6660(2) 0.91769(18) 0.54881(17) 0.0510(5) Uani 1 1 d . . . . .
H30 H 0.6660 0.9914 0.5155 0.061 Uiso 1 1 calc R U . . .
C31 C 0.7650(2) 0.83466(18) 0.50712(16) 0.0455(5) Uani 1 1 d . . . . .
C32 C 0.8690(2) 0.8613(2) 0.40569(19) 0.0688(7) Uani 1 1 d . . . . .
H32A H 0.8236 0.9034 0.3530 0.103 Uiso 1 1 calc R U . . .
H32B H 0.9136 0.7911 0.3779 0.103 Uiso 1 1 calc R U . . .
H32C H 0.9360 0.9063 0.4218 0.103 Uiso 1 1 calc R U . . .
C33 C 0.7637(2) 0.72677(17) 0.56034(16) 0.0455(5) Uani 1 1 d . . . . .
H33 H 0.8313 0.6700 0.5355 0.055 Uiso 1 1 calc R U . . .
C34 C 0.6636(2) 0.70162(16) 0.65011(15) 0.0409(5) Uani 1 1 d . . . . .
H34 H 0.6649 0.6282 0.6841 0.049 Uiso 1 1 calc R U . . .
N1 N 0.37826(17) 0.63892(14) 1.07472(12) 0.0438(4) Uani 1 1 d . . . . .
H1 H 0.4494 0.6367 1.1031 0.053 Uiso 1 1 calc R U . . .
N2 N 0.35359(17) 0.52470(13) 0.64137(12) 0.0414(4) Uani 1 1 d . . . . .
N3 N 0.24428(18) 0.69862(14) 0.58245(13) 0.0473(4) Uani 1 1 d . . . . .
O1 O 0.5376(2) 0.89858(16) 0.91293(15) 0.0834(6) Uani 1 1 d . . . . .
O2 O 0.64028(16) 0.75160(15) 0.99653(13) 0.0673(5) Uani 1 1 d . . . . .
O3 O 0.45185(15) 0.50822(11) 0.78547(11) 0.0496(4) Uani 1 1 d . . . . .
O4 O 0.2406(2) 0.53605(15) 0.50352(14) 0.0863(6) Uani 1 1 d . . . . .
O5 O 0.27790(14) 0.86290(11) 0.64553(11) 0.0466(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.373(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(2) . ?
C7 C8 1.359(3) . ?
C7 C20 1.497(2) . ?
C8 N1 1.382(2) . ?
C8 C9 1.497(3) . ?
C9 C10 1.522(3) . ?
C9 C27 1.547(2) . ?
C9 H9 0.9800 . ?
C10 O1 1.185(3) . ?
C10 O2 1.329(3) . ?
C11 C12 1.430(4) . ?
C11 O2 1.461(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.383(3) . ?
C13 C19 1.385(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C17 1.382(3) . ?
C15 C16 1.508(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.522(3) . ?
C20 C26 1.607(2) . ?
C20 H20 0.9800 . ?
C21 O3 1.210(2) . ?
C21 N2 1.381(2) . ?
C21 C26 1.521(3) . ?
C22 N2 1.472(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O4 1.205(2) . ?
C23 N3 1.372(3) . ?
C23 N2 1.390(3) . ?
C24 N3 1.472(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.207(2) . ?
C25 N3 1.384(2) . ?
C25 C26 1.519(2) . ?
C26 C27 1.564(2) . ?
C27 C28 1.523(2) . ?
C27 H27 0.9800 . ?
C28 C34 1.385(3) . ?
C28 C29 1.390(3) . ?
C29 C30 1.380(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.380(3) . ?
C30 H30 0.9300 . ?
C31 C33 1.383(3) . ?
C31 C32 1.513(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.388(3) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 129.7(2) . . ?
N1 C1 C6 108.08(16) . . ?
C2 C1 C6 122.2(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 119.30(18) . . ?
C5 C6 C7 134.19(19) . . ?
C1 C6 C7 106.47(17) . . ?
C8 C7 C6 106.94(16) . . ?
C8 C7 C20 125.88(16) . . ?
C6 C7 C20 127.17(17) . . ?
C7 C8 N1 109.99(16) . . ?
C7 C8 C9 126.37(16) . . ?
N1 C8 C9 123.59(17) . . ?
C8 C9 C10 109.32(15) . . ?
C8 C9 C27 109.27(15) . . ?
C10 C9 C27 108.80(15) . . ?
C8 C9 H9 109.8 . . ?
C10 C9 H9 109.8 . . ?
C27 C9 H9 109.8 . . ?
O1 C10 O2 123.9(2) . . ?
O1 C10 C9 125.0(2) . . ?
O2 C10 C9 111.08(19) . . ?
C12 C11 O2 111.9(2) . . ?
C12 C11 H11A 109.2 . . ?
O2 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
O2 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C19 120.75(18) . . ?
C14 C13 H13 119.6 . . ?
C19 C13 H13 119.6 . . ?
C13 C14 C15 121.71(19) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C17 C15 C14 117.55(19) . . ?
C17 C15 C16 121.4(2) . . ?
C14 C15 C16 121.0(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 121.16(19) . . ?
C15 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 121.13(19) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C13 C19 C18 117.67(18) . . ?
C13 C19 C20 122.26(16) . . ?
C18 C19 C20 119.99(17) . . ?
C7 C20 C19 114.11(15) . . ?
C7 C20 C26 108.97(14) . . ?
C19 C20 C26 113.18(14) . . ?
C7 C20 H20 106.7 . . ?
C19 C20 H20 106.7 . . ?
C26 C20 H20 106.7 . . ?
O3 C21 N2 119.41(17) . . ?
O3 C21 C26 122.77(16) . . ?
N2 C21 C26 117.72(15) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N3 121.6(2) . . ?
O4 C23 N2 121.3(2) . . ?
N3 C23 N2 117.07(17) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 N3 119.80(17) . . ?
O5 C25 C26 122.60(17) . . ?
N3 C25 C26 117.38(16) . . ?
C25 C26 C21 113.00(15) . . ?
C25 C26 C27 107.46(14) . . ?
C21 C26 C27 112.40(15) . . ?
C25 C26 C20 106.48(14) . . ?
C21 C26 C20 106.03(13) . . ?
C27 C26 C20 111.37(14) . . ?
C28 C27 C9 112.83(15) . . ?
C28 C27 C26 112.37(14) . . ?
C9 C27 C26 114.05(14) . . ?
C28 C27 H27 105.6 . . ?
C9 C27 H27 105.6 . . ?
C26 C27 H27 105.6 . . ?
C34 C28 C29 117.52(17) . . ?
C34 C28 C27 123.26(16) . . ?
C29 C28 C27 119.20(16) . . ?
C30 C29 C28 121.05(18) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 121.50(18) . . ?
C31 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?
C30 C31 C33 117.58(18) . . ?
C30 C31 C32 120.68(19) . . ?
C33 C31 C32 121.7(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 C34 121.30(19) . . ?
C31 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C28 C34 C33 120.97(17) . . ?
C28 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C1 N1 C8 108.52(16) . . ?
C1 N1 H1 125.7 . . ?
C8 N1 H1 125.7 . . ?
C21 N2 C23 125.27(16) . . ?
C21 N2 C22 118.04(17) . . ?
C23 N2 C22 116.65(17) . . ?
C23 N3 C25 124.52(16) . . ?
C23 N3 C24 117.53(18) . . ?
C25 N3 C24 117.69(18) . . ?
C10 O2 C11 117.0(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.54 3.004(2) 115.0 .
N1 H1 O3 0.86 2.38 3.022(2) 131.4 2_667

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_2aa
_database_code_depnum_ccdc_archive 'CCDC 2078847'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H33 N3 O5'
_chemical_formula_sum            'C34 H33 N3 O5'
_chemical_formula_weight         563.63

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   17.6658(12)
_cell_length_b                   12.4540(8)
_cell_length_c                   26.766(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.226(2)
_cell_angle_gamma                90
_cell_volume                     5864.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5433
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      20.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             2384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6887
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59155
_diffrn_reflns_av_unetI/netI     0.1867
_diffrn_reflns_av_R_equivalents  0.1698
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.528
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11530
_reflns_number_gt                4692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0862P)²+18.8524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11530
_refine_ls_number_parameters     767
_refine_ls_number_restraints     396
_refine_ls_R_factor_all          0.2613
_refine_ls_R_factor_gt           0.1063
_refine_ls_wR_factor_ref         0.2918
_refine_ls_wR_factor_gt          0.2190
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.053
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4509(3) 0.3611(5) 0.1435(2) 0.0457(7) Uani 1 1 d . U . . .
C2 C 0.5296(3) 0.3573(5) 0.1448(2) 0.0479(7) Uani 1 1 d . U . . .
H2 H 0.5586 0.3224 0.1706 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5629(4) 0.4063(5) 0.1069(2) 0.0496(7) Uani 1 1 d . U . . .
H3 H 0.6156 0.4056 0.1072 0.059 Uiso 1 1 calc R U . . .
C4 C 0.5201(3) 0.4569(5) 0.0682(2) 0.0496(7) Uani 1 1 d . U . . .
H4 H 0.5448 0.4914 0.0435 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4413(3) 0.4578(5) 0.0652(2) 0.0476(7) Uani 1 1 d . U . . .
H5 H 0.4131 0.4899 0.0382 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4053(3) 0.4092(5) 0.1036(2) 0.0446(6) Uani 1 1 d . U . . .
C7 C 0.3279(3) 0.3975(5) 0.1144(2) 0.0419(5) Uani 1 1 d . U . . .
C8 C 0.3287(3) 0.3473(5) 0.1593(2) 0.0405(6) Uani 1 1 d . U . . .
C9 C 0.2622(3) 0.3216(5) 0.1878(2) 0.0409(6) Uani 1 1 d . U . . .
H9 H 0.2514 0.2445 0.1852 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2795(3) 0.3519(5) 0.2427(2) 0.0415(8) Uani 1 1 d . U . . .
C11 C 0.3374(5) 0.2903(7) 0.3216(3) 0.0825(19) Uani 1 1 d . U . . .
H11A H 0.2932 0.3040 0.3396 0.099 Uiso 1 1 calc R U . . .
H11B H 0.3716 0.3512 0.3260 0.099 Uiso 1 1 calc R U . . .
C12 C 0.3766(5) 0.1895(7) 0.3401(3) 0.0848(19) Uani 1 1 d . U . . .
H12A H 0.3424 0.1299 0.3346 0.127 Uiso 1 1 calc R U . . .
H12B H 0.3918 0.1962 0.3753 0.127 Uiso 1 1 calc R U . . .
H12C H 0.4206 0.1779 0.3223 0.127 Uiso 1 1 calc R U . . .
C13 C 0.2562(3) 0.4390(5) 0.0853(2) 0.0421(5) Uani 1 1 d . U . . .
H13 H 0.2534 0.5162 0.0918 0.050 Uiso 1 1 calc R U . . .
C14 C 0.2554(3) 0.4250(5) 0.0286(2) 0.0461(6) Uani 1 1 d . U . . .
C15 C 0.2793(3) 0.3284(5) 0.0092(2) 0.0490(7) Uani 1 1 d . U . . .
H15 H 0.3002 0.2762 0.0311 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2726(3) 0.3079(5) -0.0417(2) 0.0517(7) Uani 1 1 d . U . . .
H16 H 0.2868 0.2417 -0.0539 0.062 Uiso 1 1 calc R U . . .
C17 C 0.2446(4) 0.3877(5) -0.0743(3) 0.0526(7) Uani 1 1 d . U . . .
H17 H 0.2386 0.3747 -0.1086 0.063 Uiso 1 1 calc R U . . .
C18 C 0.2256(3) 0.4855(5) -0.0560(2) 0.0512(7) Uani 1 1 d . U . . .
H18 H 0.2093 0.5394 -0.0785 0.061 Uiso 1 1 calc R U . . .
C19 C 0.2299(4) 0.5068(5) -0.0049(2) 0.0486(7) Uani 1 1 d . U . . .
C20 C 0.2092(4) 0.6178(5) 0.0107(2) 0.0520(11) Uani 1 1 d . U . . .
H20A H 0.2455 0.6422 0.0371 0.078 Uiso 1 1 calc R U . . .
H20B H 0.1594 0.6168 0.0224 0.078 Uiso 1 1 calc R U . . .
H20C H 0.2093 0.6654 -0.0175 0.078 Uiso 1 1 calc R U . . .
C21 C 0.1748(3) 0.2729(5) 0.0857(2) 0.0390(7) Uani 1 1 d . U . . .
C22 C 0.1078(4) 0.1434(5) 0.0287(3) 0.070(2) Uani 1 1 d . . . . .
H22A H 0.1000 0.0906 0.0538 0.104 Uiso 1 1 calc R U . . .
H22B H 0.1543 0.1282 0.0141 0.104 Uiso 1 1 calc R U . . .
H22C H 0.0661 0.1413 0.0031 0.104 Uiso 1 1 calc R U . . .
C23 C 0.0503(3) 0.3174(5) 0.0430(3) 0.0455(17) Uani 1 1 d . . . . .
C24 C -0.0170(4) 0.4816(6) 0.0643(3) 0.073(2) Uani 1 1 d . . . . .
H24A H -0.0340 0.4867 0.0973 0.110 Uiso 1 1 calc R U . . .
H24B H -0.0557 0.4480 0.0421 0.110 Uiso 1 1 calc R U . . .
H24C H -0.0069 0.5522 0.0522 0.110 Uiso 1 1 calc R U . . .
C25 C 0.1173(3) 0.4598(5) 0.0920(2) 0.0395(7) Uani 1 1 d . U . . .
C26 C 0.1846(3) 0.3858(5) 0.1060(2) 0.0401(5) Uani 1 1 d . U . . .
C27 C 0.1925(3) 0.3850(5) 0.1651(2) 0.0415(5) Uani 1 1 d . U . . .
H27 H 0.2007 0.4597 0.1757 0.050 Uiso 1 1 calc R U . . .
C28 C 0.1170(3) 0.3505(5) 0.1844(2) 0.0453(6) Uani 1 1 d . U . . .
C29 C 0.0910(3) 0.2464(5) 0.1762(2) 0.0469(7) Uani 1 1 d . U . . .
H29 H 0.1223 0.1966 0.1625 0.056 Uiso 1 1 calc R U . . .
C30 C 0.0202(3) 0.2146(5) 0.1879(2) 0.0494(7) Uani 1 1 d . U . . .
H30 H 0.0038 0.1445 0.1817 0.059 Uiso 1 1 calc R U . . .
C31 C -0.0262(4) 0.2875(5) 0.2088(2) 0.0509(7) Uani 1 1 d . U . . .
H31 H -0.0748 0.2675 0.2160 0.061 Uiso 1 1 calc R U . . .
C32 C -0.0006(3) 0.3892(5) 0.2190(2) 0.0504(7) Uani 1 1 d . U . . .
H32 H -0.0319 0.4369 0.2342 0.061 Uiso 1 1 calc R U . . .
C33 C 0.0702(3) 0.4242(5) 0.2075(2) 0.0485(7) Uani 1 1 d . U . . .
C34 C 0.0931(4) 0.5374(5) 0.2209(3) 0.0542(11) Uani 1 1 d . U . . .
H34A H 0.0981 0.5776 0.1907 0.081 Uiso 1 1 calc R U . . .
H34B H 0.1408 0.5370 0.2411 0.081 Uiso 1 1 calc R U . . .
H34C H 0.0550 0.5700 0.2393 0.081 Uiso 1 1 calc R U . . .
C35 C 0.1560(3) 0.8864(5) -0.0116(2) 0.0459(7) Uani 1 1 d . U . . .
C36 C 0.1266(4) 0.8853(5) -0.0615(2) 0.0483(7) Uani 1 1 d . U . . .
H36 H 0.0785 0.8583 -0.0711 0.058 Uiso 1 1 calc R U . . .
C37 C 0.1715(3) 0.9256(5) -0.0956(3) 0.0498(7) Uani 1 1 d . U . . .
H37 H 0.1529 0.9261 -0.1292 0.060 Uiso 1 1 calc R U . . .
C38 C 0.2436(3) 0.9658(5) -0.0826(2) 0.0494(7) Uani 1 1 d . U . . .
H38 H 0.2720 0.9931 -0.1072 0.059 Uiso 1 1 calc R U . . .
C39 C 0.2733(4) 0.9655(5) -0.0331(2) 0.0472(7) Uani 1 1 d . U . . .
H39 H 0.3220 0.9917 -0.0243 0.057 Uiso 1 1 calc R U . . .
C40 C 0.2292(3) 0.9251(5) 0.0037(2) 0.0444(6) Uani 1 1 d . U . . .
C41 C 0.2407(3) 0.9119(5) 0.0572(2) 0.0413(5) Uani 1 1 d . U . . .
C42 C 0.1763(3) 0.8685(5) 0.0721(2) 0.0399(6) Uani 1 1 d . U . . .
C43 C 0.1608(3) 0.8429(5) 0.1250(2) 0.0397(6) Uani 1 1 d . U . . .
H43 H 0.1638 0.7650 0.1301 0.048 Uiso 1 1 calc R U . . .
C44 C 0.0820(3) 0.8817(5) 0.1347(2) 0.0403(8) Uani 1 1 d . U . . .
C45 C -0.0478(5) 0.8365(11) 0.1306(6) 0.169(4) Uani 1 1 d . U . . .
H45A H -0.0483 0.8994 0.1519 0.203 Uiso 1 1 calc R U . . .
H45B H -0.0732 0.8549 0.0981 0.203 Uiso 1 1 calc R U . . .
C46 C -0.0860(5) 0.7556(10) 0.1510(5) 0.172(4) Uani 1 1 d . U . . .
H46A H -0.1041 0.7060 0.1251 0.258 Uiso 1 1 calc R U . . .
H46B H -0.1284 0.7845 0.1666 0.258 Uiso 1 1 calc R U . . .
H46C H -0.0526 0.7189 0.1756 0.258 Uiso 1 1 calc R U . . .
C47 C 0.3085(3) 0.9445(5) 0.0921(2) 0.0414(5) Uani 1 1 d . U . . .
H47 H 0.3054 1.0225 0.0963 0.050 Uiso 1 1 calc R U . . .
C48 C 0.3852(3) 0.9212(5) 0.0727(2) 0.0457(6) Uani 1 1 d . U . . .
C49 C 0.3973(3) 0.8230(5) 0.0504(2) 0.0483(7) Uani 1 1 d . U . . .
H49 H 0.3571 0.7748 0.0454 0.058 Uiso 1 1 calc R U . . .
C50 C 0.4677(3) 0.7945(5) 0.0354(2) 0.0510(7) Uani 1 1 d . U . . .
H50 H 0.4747 0.7284 0.0203 0.061 Uiso 1 1 calc R U . . .
C51 C 0.5261(4) 0.8654(5) 0.0433(2) 0.0521(7) Uani 1 1 d . U . . .
H51 H 0.5742 0.8462 0.0349 0.063 Uiso 1 1 calc R U . . .
C52 C 0.5153(4) 0.9632(5) 0.0630(2) 0.0514(7) Uani 1 1 d . U . . .
H52 H 0.5559 1.0109 0.0670 0.062 Uiso 1 1 calc R U . . .
C53 C 0.4453(3) 0.9949(5) 0.0776(2) 0.0490(7) Uani 1 1 d . U . . .
C54 C 0.4373(4) 1.1093(5) 0.0953(3) 0.0542(11) Uani 1 1 d . U . . .
H54A H 0.4785 1.1517 0.0850 0.081 Uiso 1 1 calc R U . . .
H54B H 0.4385 1.1103 0.1313 0.081 Uiso 1 1 calc R U . . .
H54C H 0.3899 1.1384 0.0810 0.081 Uiso 1 1 calc R U . . .
C55 C 0.3279(3) 0.7763(5) 0.1450(2) 0.0377(7) Uani 1 1 d . U . . .
C56 C 0.4096(4) 0.6313(5) 0.1771(3) 0.075(3) Uani 1 1 d . . . . .
H56A H 0.3634 0.5906 0.1758 0.112 Uiso 1 1 calc R U . . .
H56B H 0.4404 0.6149 0.2075 0.112 Uiso 1 1 calc R U . . .
H56C H 0.4369 0.6131 0.1488 0.112 Uiso 1 1 calc R U . . .
C57 C 0.4367(3) 0.8143(5) 0.2061(2) 0.0433(16) Uani 1 1 d . . . . .
C58 C 0.4679(4) 0.9945(5) 0.2364(3) 0.069(2) Uani 1 1 d . . . . .
H58A H 0.4589 0.9875 0.2711 0.103 Uiso 1 1 calc R U . . .
H58B H 0.4579 1.0671 0.2256 0.103 Uiso 1 1 calc R U . . .
H58C H 0.5199 0.9769 0.2323 0.103 Uiso 1 1 calc R U . . .
C59 C 0.3518(3) 0.9637(5) 0.1819(2) 0.0381(7) Uani 1 1 d . U . . .
C60 C 0.3028(3) 0.8928(4) 0.1456(2) 0.0388(5) Uani 1 1 d . U . . .
C61 C 0.2201(3) 0.8988(5) 0.1624(2) 0.0400(5) Uani 1 1 d . U . . .
H61 H 0.2064 0.9751 0.1622 0.048 Uiso 1 1 calc R U . . .
C62 C 0.2199(3) 0.8609(5) 0.2167(2) 0.0433(6) Uani 1 1 d . U . . .
C63 C 0.2326(3) 0.7524(5) 0.2284(2) 0.0455(7) Uani 1 1 d . U . . .
H63 H 0.2337 0.7031 0.2024 0.055 Uiso 1 1 calc R U . . .
C64 C 0.2436(3) 0.7160(5) 0.2775(2) 0.0481(7) Uani 1 1 d . U . . .
H64 H 0.2525 0.6436 0.2842 0.058 Uiso 1 1 calc R U . . .
C65 C 0.2412(3) 0.7885(5) 0.3160(3) 0.0493(7) Uani 1 1 d . U . . .
H65 H 0.2506 0.7662 0.3492 0.059 Uiso 1 1 calc R U . . .
C66 C 0.2250(3) 0.8933(5) 0.3053(2) 0.0485(7) Uani 1 1 d . U . . .
H66 H 0.2220 0.9409 0.3318 0.058 Uiso 1 1 calc R U . . .
C67 C 0.2125(3) 0.9327(5) 0.2566(2) 0.0461(7) Uani 1 1 d . U . . .
C68 C 0.1921(4) 1.0481(5) 0.2488(2) 0.0499(11) Uani 1 1 d . U . . .
H68A H 0.1832 1.0800 0.2804 0.075 Uiso 1 1 calc R U . . .
H68B H 0.1469 1.0537 0.2262 0.075 Uiso 1 1 calc R U . . .
H68C H 0.2330 1.0850 0.2349 0.075 Uiso 1 1 calc R U . . .
N1 N 0.4030(2) 0.3240(4) 0.17741(18) 0.0395(12) Uani 1 1 d . . . . .
H1 H 0.4168 0.2918 0.2052 0.047 Uiso 1 1 calc R U . . .
N2 N 0.1124(3) 0.2515(4) 0.05192(18) 0.0404(13) Uani 1 1 d . . . . .
N3 N 0.0535(2) 0.4164(4) 0.06641(19) 0.0418(13) Uani 1 1 d . . . . .
N4 N 0.1239(2) 0.8536(4) 0.03109(18) 0.0394(13) Uani 1 1 d . . . . .
H4A H 0.0788 0.8282 0.0320 0.047 Uiso 1 1 calc R U . . .
N5 N 0.3917(3) 0.7466(4) 0.17570(18) 0.0399(13) Uani 1 1 d . . . . .
N6 N 0.4173(3) 0.9212(4) 0.20589(18) 0.0401(13) Uani 1 1 d . . . . .
O1 O 0.2660(4) 0.4357(4) 0.2608(2) 0.097(2) Uani 1 1 d . . . . .
O2 O 0.3148(3) 0.2720(4) 0.26802(16) 0.0565(12) Uani 1 1 d . . . . .
O3 O 0.2202(2) 0.2023(3) 0.09676(15) 0.0444(11) Uani 1 1 d . . . . .
O4 O -0.0051(3) 0.2905(4) 0.0164(2) 0.0763(17) Uani 1 1 d . . . . .
O5 O 0.1179(2) 0.5524(3) 0.10540(17) 0.0526(12) Uani 1 1 d . . . . .
O6 O 0.0672(3) 0.9696(4) 0.1470(2) 0.0841(17) Uani 1 1 d . . . . .
O7 O 0.0309(2) 0.8064(4) 0.1247(2) 0.0860(18) Uani 1 1 d . . . . .
O8 O 0.2925(2) 0.7096(3) 0.11976(15) 0.0402(10) Uani 1 1 d . . . . .
O9 O 0.4912(3) 0.7801(4) 0.23189(19) 0.0719(16) Uani 1 1 d . . . . .
O10 O 0.3362(2) 1.0573(3) 0.18793(15) 0.0462(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.376(7) . ?
C1 C2 1.388(8) . ?
C1 C6 1.411(8) . ?
C2 C3 1.361(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.430(8) . ?
C7 C8 1.355(8) . ?
C7 C13 1.516(8) . ?
C8 N1 1.387(7) . ?
C8 C9 1.492(8) . ?
C9 C10 1.522(8) . ?
C9 C27 1.539(8) . ?
C9 H9 0.9800 . ?
C10 O1 1.184(7) . ?
C10 O2 1.327(7) . ?
C11 O2 1.471(8) . ?
C11 C12 1.495(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.526(8) . ?
C13 C26 1.573(8) . ?
C13 H13 0.9800 . ?
C14 C15 1.390(8) . ?
C14 C19 1.404(8) . ?
C15 C16 1.382(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.499(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O3 1.209(6) . ?
C21 N2 1.387(7) . ?
C21 C26 1.511(8) . ?
C22 N2 1.483(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O4 1.206(7) . ?
C23 N2 1.373(7) . ?
C23 N3 1.381(7) . ?
C24 N3 1.483(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.208(7) . ?
C25 N3 1.375(7) . ?
C25 C26 1.523(8) . ?
C26 C27 1.577(8) . ?
C27 C28 1.533(8) . ?
C27 H27 0.9800 . ?
C28 C29 1.387(8) . ?
C28 C33 1.415(8) . ?
C29 C30 1.375(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.364(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.385(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.501(8) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 N4 1.382(8) . ?
C35 C36 1.388(8) . ?
C35 C40 1.405(8) . ?
C36 C37 1.358(8) . ?
C36 H36 0.9300 . ?
C37 C38 1.383(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.379(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.405(8) . ?
C39 H39 0.9300 . ?
C40 C41 1.436(8) . ?
C41 C42 1.352(8) . ?
C41 C47 1.505(8) . ?
C42 N4 1.382(7) . ?
C42 C43 1.501(8) . ?
C43 C44 1.519(8) . ?
C43 C61 1.548(8) . ?
C43 H43 0.9800 . ?
C44 O6 1.179(7) . ?
C44 O7 1.311(7) . ?
C45 C46 1.355(14) . ?
C45 O7 1.462(10) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 C48 1.523(8) . ?
C47 C60 1.583(8) . ?
C47 H47 0.9800 . ?
C48 C49 1.386(8) . ?
C48 C53 1.399(8) . ?
C49 C50 1.386(8) . ?
C49 H49 0.9300 . ?
C50 C51 1.360(8) . ?
C50 H50 0.9300 . ?
C51 C52 1.348(8) . ?
C51 H51 0.9300 . ?
C52 C53 1.388(8) . ?
C52 H52 0.9300 . ?
C53 C54 1.512(9) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C55 O8 1.209(6) . ?
C55 N5 1.382(7) . ?
C55 C60 1.518(8) . ?
C56 N5 1.471(7) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 O9 1.210(7) . ?
C57 N5 1.374(7) . ?
C57 N6 1.374(7) . ?
C58 N6 1.472(7) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 O10 1.212(6) . ?
C59 N6 1.376(7) . ?
C59 C60 1.524(8) . ?
C60 C61 1.569(8) . ?
C61 C62 1.530(8) . ?
C61 H61 0.9800 . ?
C62 C63 1.400(8) . ?
C62 C67 1.407(8) . ?
C63 C64 1.386(8) . ?
C63 H63 0.9300 . ?
C64 C65 1.375(8) . ?
C64 H64 0.9300 . ?
C65 C66 1.361(8) . ?
C65 H65 0.9300 . ?
C66 C67 1.392(8) . ?
C66 H66 0.9300 . ?
C67 C68 1.492(8) . ?
C68 H68A 0.9600 . ?
C68 H68B 0.9600 . ?
C68 H68C 0.9600 . ?
N1 H1 0.8600 . ?
N4 H4A 0.8600 . ?

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
N1 C1 C2 130.4(6) . . ?
N1 C1 C6 107.3(5) . . ?
C2 C1 C6 122.3(6) . . ?
C3 C2 C1 117.8(6) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.4(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 121.7(6) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 118.4(6) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 118.3(5) . . ?
C5 C6 C7 134.4(6) . . ?
C1 C6 C7 107.2(5) . . ?
C8 C7 C6 107.0(5) . . ?
C8 C7 C13 123.7(5) . . ?
C6 C7 C13 129.2(6) . . ?
C7 C8 N1 109.9(5) . . ?
C7 C8 C9 127.3(5) . . ?
N1 C8 C9 122.8(5) . . ?
C8 C9 C10 109.9(5) . . ?
C8 C9 C27 109.2(5) . . ?
C10 C9 C27 109.6(5) . . ?
C8 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
C27 C9 H9 109.3 . . ?
O1 C10 O2 123.7(6) . . ?
O1 C10 C9 125.7(6) . . ?
O2 C10 C9 110.6(5) . . ?
O2 C11 C12 105.7(6) . . ?
O2 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
O2 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C14 113.8(5) . . ?
C7 C13 C26 109.7(5) . . ?
C14 C13 C26 111.6(5) . . ?
C7 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C26 C13 H13 107.2 . . ?
C15 C14 C19 118.7(6) . . ?
C15 C14 C13 119.6(6) . . ?
C19 C14 C13 121.7(6) . . ?
C16 C15 C14 121.7(6) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 118.8(6) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 120.1(6) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 122.0(6) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C14 118.4(6) . . ?
C18 C19 C20 117.2(6) . . ?
C14 C19 C20 124.3(6) . . ?
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 . . ?
O3 C21 N2 119.4(5) . . ?
O3 C21 C26 122.5(5) . . ?
N2 C21 C26 118.1(5) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N2 122.0(6) . . ?
O4 C23 N3 120.9(6) . . ?
N2 C23 N3 117.1(5) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 N3 120.6(5) . . ?
O5 C25 C26 121.2(5) . . ?
N3 C25 C26 118.1(5) . . ?
C21 C26 C25 114.4(5) . . ?
C21 C26 C13 109.5(5) . . ?
C25 C26 C13 107.1(5) . . ?
C21 C26 C27 110.5(5) . . ?
C25 C26 C27 104.2(5) . . ?
C13 C26 C27 110.9(5) . . ?
C28 C27 C9 114.4(5) . . ?
C28 C27 C26 109.8(5) . . ?
C9 C27 C26 113.1(5) . . ?
C28 C27 H27 106.3 . . ?
C9 C27 H27 106.3 . . ?
C26 C27 H27 106.3 . . ?
C29 C28 C33 118.5(6) . . ?
C29 C28 C27 119.6(5) . . ?
C33 C28 C27 121.7(5) . . ?
C30 C29 C28 121.9(6) . . ?
C30 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?
C31 C30 C29 119.4(6) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C32 C31 C30 119.7(6) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 122.5(6) . . ?
C31 C32 H32 118.7 . . ?
C33 C32 H32 118.7 . . ?
C32 C33 C28 117.9(6) . . ?
C32 C33 C34 118.1(6) . . ?
C28 C33 C34 123.9(6) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N4 C35 C36 130.3(6) . . ?
N4 C35 C40 107.2(5) . . ?
C36 C35 C40 122.5(6) . . ?
C37 C36 C35 117.0(6) . . ?
C37 C36 H36 121.5 . . ?
C35 C36 H36 121.5 . . ?
C36 C37 C38 123.0(6) . . ?
C36 C37 H37 118.5 . . ?
C38 C37 H37 118.5 . . ?
C39 C38 C37 120.1(6) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C38 C39 C40 119.2(6) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C39 C40 C35 118.2(6) . . ?
C39 C40 C41 134.6(6) . . ?
C35 C40 C41 107.2(5) . . ?
C42 C41 C40 107.0(5) . . ?
C42 C41 C47 124.6(6) . . ?
C40 C41 C47 128.3(5) . . ?
C41 C42 N4 109.9(5) . . ?
C41 C42 C43 126.5(5) . . ?
N4 C42 C43 123.6(5) . . ?
C42 C43 C44 110.1(5) . . ?
C42 C43 C61 110.1(5) . . ?
C44 C43 C61 108.8(5) . . ?
C42 C43 H43 109.3 . . ?
C44 C43 H43 109.3 . . ?
C61 C43 H43 109.3 . . ?
O6 C44 O7 123.7(6) . . ?
O6 C44 C43 125.0(6) . . ?
O7 C44 C43 111.2(5) . . ?
C46 C45 O7 111.5(10) . . ?
C46 C45 H45A 109.3 . . ?
O7 C45 H45A 109.3 . . ?
C46 C45 H45B 109.3 . . ?
O7 C45 H45B 109.3 . . ?
H45A C45 H45B 108.0 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C41 C47 C48 114.8(5) . . ?
C41 C47 C60 109.8(5) . . ?
C48 C47 C60 111.3(5) . . ?
C41 C47 H47 106.8 . . ?
C48 C47 H47 106.8 . . ?
C60 C47 H47 106.8 . . ?
C49 C48 C53 118.3(6) . . ?
C49 C48 C47 119.5(5) . . ?
C53 C48 C47 122.2(6) . . ?
C50 C49 C48 121.9(6) . . ?
C50 C49 H49 119.1 . . ?
C48 C49 H49 119.1 . . ?
C51 C50 C49 118.4(6) . . ?
C51 C50 H50 120.8 . . ?
C49 C50 H50 120.8 . . ?
C52 C51 C50 121.0(6) . . ?
C52 C51 H51 119.5 . . ?
C50 C51 H51 119.5 . . ?
C51 C52 C53 121.9(6) . . ?
C51 C52 H52 119.1 . . ?
C53 C52 H52 119.1 . . ?
C52 C53 C48 118.3(6) . . ?
C52 C53 C54 117.8(6) . . ?
C48 C53 C54 123.8(6) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O8 C55 N5 120.0(5) . . ?
O8 C55 C60 121.7(5) . . ?
N5 C55 C60 118.2(5) . . ?
N5 C56 H56A 109.5 . . ?
N5 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
N5 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
O9 C57 N5 120.6(6) . . ?
O9 C57 N6 121.9(5) . . ?
N5 C57 N6 117.5(5) . . ?
N6 C58 H58A 109.5 . . ?
N6 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
N6 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
O10 C59 N6 120.0(5) . . ?
O10 C59 C60 121.3(5) . . ?
N6 C59 C60 118.6(5) . . ?
C55 C60 C59 114.3(5) . . ?
C55 C60 C61 109.3(5) . . ?
C59 C60 C61 106.2(5) . . ?
C55 C60 C47 109.7(5) . . ?
C59 C60 C47 105.2(5) . . ?
C61 C60 C47 112.2(4) . . ?
C62 C61 C43 114.6(5) . . ?
C62 C61 C60 109.9(5) . . ?
C43 C61 C60 112.8(5) . . ?
C62 C61 H61 106.3 . . ?
C43 C61 H61 106.3 . . ?
C60 C61 H61 106.3 . . ?
C63 C62 C67 117.8(6) . . ?
C63 C62 C61 119.8(6) . . ?
C67 C62 C61 122.2(5) . . ?
C64 C63 C62 122.3(6) . . ?
C64 C63 H63 118.9 . . ?
C62 C63 H63 118.9 . . ?
C65 C64 C63 119.0(6) . . ?
C65 C64 H64 120.5 . . ?
C63 C64 H64 120.5 . . ?
C66 C65 C64 119.4(6) . . ?
C66 C65 H65 120.3 . . ?
C64 C65 H65 120.3 . . ?
C65 C66 C67 123.2(6) . . ?
C65 C66 H66 118.4 . . ?
C67 C66 H66 118.4 . . ?
C66 C67 C62 118.0(6) . . ?
C66 C67 C68 119.0(6) . . ?
C62 C67 C68 123.0(6) . . ?
C67 C68 H68A 109.5 . . ?
C67 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C67 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C1 N1 C8 108.6(5) . . ?
C1 N1 H1 125.7 . . ?
C8 N1 H1 125.7 . . ?
C23 N2 C21 125.0(5) . . ?
C23 N2 C22 117.3(5) . . ?
C21 N2 C22 117.3(5) . . ?
C25 N3 C23 125.0(5) . . ?
C25 N3 C24 116.8(5) . . ?
C23 N3 C24 118.1(5) . . ?
C35 N4 C42 108.7(5) . . ?
C35 N4 H4A 125.6 . . ?
C42 N4 H4A 125.6 . . ?
C57 N5 C55 125.7(5) . . ?
C57 N5 C56 118.2(5) . . ?
C55 N5 C56 116.0(5) . . ?
C57 N6 C59 125.0(5) . . ?
C57 N6 C58 117.4(5) . . ?
C59 N6 C58 117.5(5) . . ?
C10 O2 C11 117.1(5) . . ?
C44 O7 C45 115.9(7) . . ?

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
N4 H4A O4 0.86 2.29 2.959(6) 134.6 3_565
N1 H1 O9 0.86 2.24 2.976(6) 144.1 2_645
N1 H1 O2 0.86 2.59 3.069(6) 116.6 .

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_3oo
_database_code_depnum_ccdc_archive 'CCDC 2078850'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H31 N3 O8'
_chemical_formula_sum            'C34 H31 N3 O8'
_chemical_formula_weight         609.62

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8318(6)
_cell_length_b                   11.4013(7)
_cell_length_c                   15.4837(8)
_cell_angle_alpha                105.432(2)
_cell_angle_beta                 103.175(2)
_cell_angle_gamma                103.079(2)
_cell_volume                     1708.79(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3969
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      21.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17530
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.946
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             6537
_reflns_number_gt                3219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1043P)²+2.4570P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6537
_refine_ls_number_parameters     478
_refine_ls_number_restraints     205
_refine_ls_R_factor_all          0.1818
_refine_ls_R_factor_gt           0.0946
_refine_ls_wR_factor_ref         0.2804
_refine_ls_wR_factor_gt          0.2299
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6194(5) -0.0097(4) 0.2784(4) 0.0616(13) Uani 1 1 d . . . . .
C2 C 0.6950(5) -0.0932(5) 0.2696(5) 0.0800(17) Uani 1 1 d . . . . .
H2 H 0.7102 -0.1366 0.3120 0.096 Uiso 1 1 calc R U . . .
C3 C 0.7463(6) -0.1090(6) 0.1954(5) 0.0905(19) Uani 1 1 d . . . . .
H3 H 0.7992 -0.1626 0.1888 0.109 Uiso 1 1 calc R U . . .
C4 C 0.7219(6) -0.0477(6) 0.1304(5) 0.0871(18) Uani 1 1 d . . . . .
H4 H 0.7576 -0.0617 0.0807 0.104 Uiso 1 1 calc R U . . .
C5 C 0.6454(5) 0.0339(5) 0.1381(4) 0.0743(15) Uani 1 1 d . . . . .
H5 H 0.6289 0.0745 0.0939 0.089 Uiso 1 1 calc R U . . .
C6 C 0.5930(5) 0.0546(4) 0.2135(3) 0.0591(13) Uani 1 1 d . . . . .
C7 C 0.5110(4) 0.1295(4) 0.2449(3) 0.0506(11) Uani 1 1 d . . . . .
C8 C 0.4911(4) 0.1074(4) 0.3227(3) 0.0516(11) Uani 1 1 d . . . . .
C9 C 0.4064(4) 0.1613(4) 0.3756(3) 0.0518(11) Uani 1 1 d . . . . .
H9 H 0.4632 0.2410 0.4258 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3422(6) 0.0714(5) 0.4203(5) 0.0670(14) Uani 1 1 d . . . . .
C11 C 0.1490(16) -0.1231(14) 0.3798(12) 0.099(2) Uani 0.487(10) 1 d D U P A 1
H11A H 0.2029 -0.1582 0.4189 0.119 Uiso 0.487(10) 1 calc R U P A 1
H11B H 0.0957 -0.1901 0.3208 0.119 Uiso 0.487(10) 1 calc R U P A 1
C12 C 0.0616(14) -0.0621(14) 0.4303(12) 0.105(3) Uani 0.487(10) 1 d D U P A 1
H12A H 0.1171 0.0101 0.4844 0.158 Uiso 0.487(10) 1 calc R U P A 1
H12B H 0.0087 -0.1236 0.4498 0.158 Uiso 0.487(10) 1 calc R U P A 1
H12C H 0.0042 -0.0346 0.3882 0.158 Uiso 0.487(10) 1 calc R U P A 1
C11' C 0.1741(11) -0.0821(14) 0.4253(11) 0.098(2) Uani 0.513(10) 1 d D U P A 2
H11C H 0.2170 -0.1449 0.4369 0.117 Uiso 0.513(10) 1 calc R U P A 2
H11D H 0.1803 -0.0219 0.4849 0.117 Uiso 0.513(10) 1 calc R U P A 2
C12' C 0.0302(10) -0.1450(14) 0.3621(11) 0.108(3) Uani 0.513(10) 1 d D U P A 2
H12D H -0.0028 -0.0829 0.3409 0.162 Uiso 0.513(10) 1 calc R U P A 2
H12E H -0.0235 -0.1780 0.3969 0.162 Uiso 0.513(10) 1 calc R U P A 2
H12F H 0.0263 -0.2136 0.3088 0.162 Uiso 0.513(10) 1 calc R U P A 2
C13 C 0.4507(4) 0.2123(4) 0.1995(3) 0.0493(11) Uani 1 1 d . . . . .
H13 H 0.3841 0.1543 0.1401 0.059 Uiso 1 1 calc R U . . .
C14 C 0.5515(5) 0.3006(4) 0.1729(3) 0.0536(12) Uani 1 1 d . . . . .
C15 C 0.6802(5) 0.3619(5) 0.2320(3) 0.0615(13) Uani 1 1 d . . . . .
H15 H 0.7060 0.3469 0.2886 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7711(6) 0.4442(5) 0.2099(4) 0.0779(16) Uani 1 1 d . . . . .
H16 H 0.8571 0.4850 0.2508 0.094 Uiso 1 1 calc R U . . .
C17 C 0.7327(6) 0.4651(6) 0.1264(4) 0.0837(17) Uani 1 1 d . . . . .
C18 C 0.6075(7) 0.4040(6) 0.0640(4) 0.0833(17) Uani 1 1 d . . . . .
H18 H 0.5838 0.4180 0.0069 0.100 Uiso 1 1 calc R U . . .
C19 C 0.5175(5) 0.3216(5) 0.0872(3) 0.0678(14) Uani 1 1 d . . . . .
H19 H 0.4324 0.2792 0.0450 0.081 Uiso 1 1 calc R U . . .
C20 C 0.2595(5) 0.3059(5) 0.1869(3) 0.0580(12) Uani 1 1 d . . . . .
C21 C 0.2294(6) 0.4271(6) 0.2086(5) 0.1069(19) Uani 1 1 d . U . . .
H21A H 0.1616 0.4189 0.2400 0.128 Uiso 1 1 calc R U . . .
H21B H 0.1890 0.4363 0.1490 0.128 Uiso 1 1 calc R U . . .
C22 C 0.3354(6) 0.5487(5) 0.2660(4) 0.0803(13) Uani 1 1 d . U . . .
C23 C 0.2813(12) 0.6626(10) 0.3064(9) 0.096(3) Uani 0.571(8) 1 d . U P B 1
H23A H 0.2126 0.6334 0.3324 0.143 Uiso 0.571(8) 1 calc R U P B 1
H23B H 0.2456 0.6924 0.2566 0.143 Uiso 0.571(8) 1 calc R U P B 1
H23C H 0.3528 0.7311 0.3548 0.143 Uiso 0.571(8) 1 calc R U P B 1
C24 C 0.4160(13) 0.5856(12) 0.2056(9) 0.102(3) Uani 0.571(8) 1 d . U P B 1
H24A H 0.4807 0.6680 0.2399 0.153 Uiso 0.571(8) 1 calc R U P B 1
H24B H 0.3585 0.5892 0.1498 0.153 Uiso 0.571(8) 1 calc R U P B 1
H24C H 0.4608 0.5235 0.1884 0.153 Uiso 0.571(8) 1 calc R U P B 1
C23' C 0.2759(17) 0.5739(16) 0.3446(12) 0.110(3) Uani 0.429(8) 1 d . U P B 2
H23D H 0.2924 0.5196 0.3809 0.165 Uiso 0.429(8) 1 calc R U P B 2
H23E H 0.1816 0.5567 0.3191 0.165 Uiso 0.429(8) 1 calc R U P B 2
H23F H 0.3154 0.6617 0.3843 0.165 Uiso 0.429(8) 1 calc R U P B 2
C24' C 0.3477(15) 0.6523(14) 0.2202(11) 0.089(3) Uani 0.429(8) 1 d . U P B 2
H24D H 0.3951 0.7341 0.2677 0.133 Uiso 0.429(8) 1 calc R U P B 2
H24E H 0.2605 0.6523 0.1887 0.133 Uiso 0.429(8) 1 calc R U P B 2
H24F H 0.3954 0.6354 0.1754 0.133 Uiso 0.429(8) 1 calc R U P B 2
C25 C 0.4440(8) 0.5296(7) 0.3278(6) 0.143(2) Uani 1 1 d . U . . .
H25A H 0.5236 0.5758 0.3180 0.172 Uiso 1 1 calc R U . . .
H25B H 0.4466 0.5761 0.3909 0.172 Uiso 1 1 calc R U . . .
C26 C 0.4642(5) 0.4126(4) 0.3324(3) 0.0508(11) Uani 1 1 d . . . . .
C27 C 0.3724(4) 0.2854(4) 0.2579(3) 0.0466(11) Uani 1 1 d . . . . .
C28 C 0.3026(4) 0.1941(4) 0.3062(3) 0.0479(11) Uani 1 1 d . . . . .
H28 H 0.2506 0.1134 0.2554 0.057 Uiso 1 1 calc R U . . .
C29 C 0.2052(4) 0.2393(4) 0.3523(3) 0.0461(10) Uani 1 1 d . . . . .
C30 C 0.2462(4) 0.3263(4) 0.4429(3) 0.0513(11) Uani 1 1 d . . . . .
H30 H 0.3369 0.3622 0.4747 0.062 Uiso 1 1 calc R U . . .
C31 C 0.1575(5) 0.3611(4) 0.4871(3) 0.0565(12) Uani 1 1 d . . . . .
H31 H 0.1871 0.4197 0.5478 0.068 Uiso 1 1 calc R U . . .
C32 C 0.0234(4) 0.3071(4) 0.4394(3) 0.0504(11) Uani 1 1 d . . . . .
C33 C -0.0225(5) 0.2217(4) 0.3487(4) 0.0585(12) Uani 1 1 d . . . . .
H33 H -0.1133 0.1876 0.3169 0.070 Uiso 1 1 calc R U . . .
C34 C 0.0693(4) 0.1882(4) 0.3065(3) 0.0554(12) Uani 1 1 d . . . . .
H34 H 0.0394 0.1298 0.2456 0.067 Uiso 1 1 calc R U . . .
N1 N 0.5567(4) 0.0236(4) 0.3451(3) 0.0597(11) Uani 1 1 d . . . . .
H1 H 0.5581 -0.0029 0.3922 0.072 Uiso 1 1 calc R U . . .
N3 N -0.0728(4) 0.3411(4) 0.4871(3) 0.0640(11) Uani 1 1 d . . . . .
O1 O 0.3909(5) 0.0791(5) 0.5001(3) 0.1066(15) Uani 1 1 d . . . . .
O2 O 0.2327(4) -0.0143(4) 0.3638(3) 0.0957(13) Uani 1 1 d . U . . .
N2 N 0.821(2) 0.566(2) 0.1066(16) 0.119(4) Uani 0.617(16) 1 d . U P C 1
O3 O 0.7763(13) 0.5979(13) 0.0392(9) 0.117(3) Uani 0.617(16) 1 d . U P C 1
O4 O 0.9337(13) 0.6227(15) 0.1662(9) 0.137(4) Uani 0.617(16) 1 d . U P C 1
N2' N 0.844(4) 0.528(3) 0.093(3) 0.122(4) Uani 0.383(16) 1 d . U P C 1
O3' O 0.817(2) 0.544(2) 0.0207(15) 0.126(4) Uani 0.383(16) 1 d . U P C 1
O4' O 0.955(2) 0.554(2) 0.1320(15) 0.125(4) Uani 0.383(16) 1 d . U P C 1
O5 O 0.1918(5) 0.2199(5) 0.1188(3) 0.1247(19) Uani 1 1 d . . . . .
O6 O 0.5521(4) 0.4171(3) 0.3954(2) 0.0799(11) Uani 1 1 d . . . . .
O7 O -0.0284(4) 0.4141(4) 0.5689(3) 0.0835(11) Uani 1 1 d . . . . .
O8 O -0.1907(4) 0.2956(4) 0.4437(3) 0.0920(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.378(6) . ?
C1 C2 1.389(7) . ?
C1 C6 1.410(7) . ?
C2 C3 1.373(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(6) . ?
C7 C8 1.347(6) . ?
C7 C13 1.495(6) . ?
C8 N1 1.381(5) . ?
C8 C9 1.491(6) . ?
C9 C10 1.513(7) . ?
C9 C28 1.554(6) . ?
C9 H9 0.9800 . ?
C10 O1 1.198(6) . ?
C10 O2 1.294(6) . ?
C11 O2 1.475(14) . ?
C11 C12 1.528(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11' C12' 1.526(5) . ?
C11' O2 1.534(15) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13 C14 1.518(6) . ?
C13 C27 1.581(6) . ?
C13 H13 0.9800 . ?
C14 C15 1.381(6) . ?
C14 C19 1.393(6) . ?
C15 C16 1.369(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(8) . ?
C17 N2 1.47(2) . ?
C17 N2' 1.52(4) . ?
C18 C19 1.374(7) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O5 1.176(6) . ?
C20 C21 1.462(8) . ?
C20 C27 1.553(6) . ?
C21 C22 1.479(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C25 1.435(8) . ?
C22 C24 1.493(12) . ?
C22 C23' 1.494(16) . ?
C22 C24' 1.528(14) . ?
C22 C23 1.581(12) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23' H23D 0.9600 . ?
C23' H23E 0.9600 . ?
C23' H23F 0.9600 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
C25 C26 1.418(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O6 1.178(5) . ?
C26 C27 1.535(6) . ?
C27 C28 1.591(6) . ?
C28 C29 1.510(6) . ?
C28 H28 0.9800 . ?
C29 C34 1.388(6) . ?
C29 C30 1.388(6) . ?
C30 C31 1.369(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.379(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.378(6) . ?
C32 N3 1.471(6) . ?
C33 C34 1.378(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 H1 0.8600 . ?
N3 O8 1.215(5) . ?
N3 O7 1.228(5) . ?
N2 O3 1.23(2) . ?
N2 O4 1.25(2) . ?
N2' O4' 1.14(3) . ?
N2' O3' 1.17(3) . ?

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
N1 C1 C2 129.5(5) . . ?
N1 C1 C6 108.5(4) . . ?
C2 C1 C6 122.1(5) . . ?
C3 C2 C1 117.2(6) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 122.2(6) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 120.9(6) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.9(6) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 118.8(5) . . ?
C5 C6 C7 135.4(5) . . ?
C1 C6 C7 105.9(4) . . ?
C8 C7 C6 107.4(4) . . ?
C8 C7 C13 124.5(4) . . ?
C6 C7 C13 128.0(4) . . ?
C7 C8 N1 110.5(4) . . ?
C7 C8 C9 125.2(4) . . ?
N1 C8 C9 124.3(4) . . ?
C8 C9 C10 111.9(4) . . ?
C8 C9 C28 107.5(4) . . ?
C10 C9 C28 112.6(4) . . ?
C8 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C28 C9 H9 108.2 . . ?
O1 C10 O2 124.2(5) . . ?
O1 C10 C9 122.3(5) . . ?
O2 C10 C9 113.6(5) . . ?
O2 C11 C12 102.7(10) . . ?
O2 C11 H11A 111.2 . . ?
C12 C11 H11A 111.2 . . ?
O2 C11 H11B 111.2 . . ?
C12 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12' C11' O2 100.1(10) . . ?
C12' C11' H11C 111.7 . . ?
O2 C11' H11C 111.7 . . ?
C12' C11' H11D 111.7 . . ?
O2 C11' H11D 111.7 . . ?
H11C C11' H11D 109.5 . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C7 C13 C14 112.0(4) . . ?
C7 C13 C27 113.3(3) . . ?
C14 C13 C27 112.7(4) . . ?
C7 C13 H13 106.0 . . ?
C14 C13 H13 106.0 . . ?
C27 C13 H13 106.0 . . ?
C15 C14 C19 117.6(4) . . ?
C15 C14 C13 121.4(4) . . ?
C19 C14 C13 121.0(4) . . ?
C16 C15 C14 122.0(5) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C17 C16 C15 118.6(5) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 121.8(5) . . ?
C16 C17 N2 119.8(11) . . ?
C18 C17 N2 118.1(11) . . ?
C16 C17 N2' 116.4(18) . . ?
C18 C17 N2' 119.6(17) . . ?
N2 C17 N2' 21.3(15) . . ?
C17 C18 C19 119.0(5) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 121.0(5) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
O5 C20 C21 120.0(5) . . ?
O5 C20 C27 119.4(5) . . ?
C21 C20 C27 120.4(5) . . ?
C20 C21 C22 120.9(5) . . ?
C20 C21 H21A 107.1 . . ?
C22 C21 H21A 107.1 . . ?
C20 C21 H21B 107.1 . . ?
C22 C21 H21B 107.1 . . ?
H21A C21 H21B 106.8 . . ?
C25 C22 C21 112.1(5) . . ?
C25 C22 C24 93.5(8) . . ?
C21 C22 C24 108.0(7) . . ?
C25 C22 C23' 88.8(9) . . ?
C21 C22 C23' 94.3(8) . . ?
C25 C22 C24' 125.3(8) . . ?
C21 C22 C24' 114.9(8) . . ?
C23' C22 C24' 113.6(9) . . ?
C25 C22 C23 118.5(7) . . ?
C21 C22 C23 113.9(6) . . ?
C24 C22 C23 108.4(7) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C23' H23D 109.5 . . ?
C22 C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22 C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C22 C24' H24D 109.5 . . ?
C22 C24' H24E 109.5 . . ?
H24D C24' H24E 109.5 . . ?
C22 C24' H24F 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C26 C25 C22 128.2(6) . . ?
C26 C25 H25A 105.2 . . ?
C22 C25 H25A 105.2 . . ?
C26 C25 H25B 105.2 . . ?
C22 C25 H25B 105.2 . . ?
H25A C25 H25B 106.0 . . ?
O6 C26 C25 117.7(5) . . ?
O6 C26 C27 122.0(4) . . ?
C25 C26 C27 120.3(5) . . ?
C26 C27 C20 111.5(4) . . ?
C26 C27 C13 112.1(3) . . ?
C20 C27 C13 107.6(3) . . ?
C26 C27 C28 110.4(3) . . ?
C20 C27 C28 106.9(3) . . ?
C13 C27 C28 108.0(3) . . ?
C29 C28 C9 110.8(3) . . ?
C29 C28 C27 115.5(3) . . ?
C9 C28 C27 111.6(3) . . ?
C29 C28 H28 106.1 . . ?
C9 C28 H28 106.1 . . ?
C27 C28 H28 106.1 . . ?
C34 C29 C30 117.5(4) . . ?
C34 C29 C28 120.2(4) . . ?
C30 C29 C28 122.1(4) . . ?
C31 C30 C29 122.2(4) . . ?
C31 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C30 C31 C32 118.4(4) . . ?
C30 C31 H31 120.8 . . ?
C32 C31 H31 120.8 . . ?
C33 C32 C31 121.7(4) . . ?
C33 C32 N3 119.4(4) . . ?
C31 C32 N3 118.8(4) . . ?
C34 C33 C32 118.4(4) . . ?
C34 C33 H33 120.8 . . ?
C32 C33 H33 120.8 . . ?
C33 C34 C29 121.7(4) . . ?
C33 C34 H34 119.1 . . ?
C29 C34 H34 119.1 . . ?
C1 N1 C8 107.8(4) . . ?
C1 N1 H1 126.1 . . ?
C8 N1 H1 126.1 . . ?
O8 N3 O7 124.0(5) . . ?
O8 N3 C32 118.4(5) . . ?
O7 N3 C32 117.6(4) . . ?
C10 O2 C11 128.9(8) . . ?
C10 O2 C11' 105.3(6) . . ?
O3 N2 O4 124.1(16) . . ?
O3 N2 C17 118.7(17) . . ?
O4 N2 C17 116.7(16) . . ?
O4' N2' O3' 117(3) . . ?
O4' N2' C17 124(3) . . ?
O3' N2' C17 119(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.10 2.937(5) 163.9 2_656

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.053


####################################################################### 
# 
# 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_5g
_database_code_depnum_ccdc_archive 'CCDC 2078852'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H27 Cl2 N O4'
_chemical_formula_sum            'C34 H27 Cl2 N O4'
_chemical_formula_weight         584.46

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7954(11)
_cell_length_b                   11.0062(10)
_cell_length_c                   13.5566(12)
_cell_angle_alpha                68.256(3)
_cell_angle_beta                 87.382(3)
_cell_angle_gamma                86.599(3)
_cell_volume                     1493.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6586
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21316
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5862
_reflns_number_gt                3662
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1020P)²+2.0422P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5862
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2348
_refine_ls_wR_factor_gt          0.2039
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3231(3) 0.6085(4) -0.2331(3) 0.0393(9) Uani 1 1 d . . . . .
C2 C 0.3633(4) 0.6451(5) -0.3386(3) 0.0538(11) Uani 1 1 d . . . . .
H2 H 0.3406 0.7264 -0.3890 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4379(4) 0.5562(5) -0.3652(4) 0.0631(13) Uani 1 1 d . . . . .
H3 H 0.4661 0.5779 -0.4352 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4725(4) 0.4345(5) -0.2903(4) 0.0603(12) Uani 1 1 d . . . . .
H4 H 0.5230 0.3768 -0.3116 0.072 Uiso 1 1 calc R U . . .
C5 C 0.4338(4) 0.3972(4) -0.1855(3) 0.0499(10) Uani 1 1 d . . . . .
H5 H 0.4579 0.3158 -0.1359 0.060 Uiso 1 1 calc R U . . .
C6 C 0.3566(3) 0.4864(3) -0.1558(3) 0.0374(8) Uani 1 1 d . . . . .
C7 C 0.2948(3) 0.4819(3) -0.0574(3) 0.0340(8) Uani 1 1 d . . . . .
C8 C 0.2287(3) 0.6044(3) -0.0805(3) 0.0328(8) Uani 1 1 d . . . . .
C9 C 0.1557(3) 0.6328(3) -0.0030(3) 0.0325(8) Uani 1 1 d . . . . .
C10 C 0.0860(3) 0.7620(4) -0.0275(3) 0.0409(9) Uani 1 1 d . . . . .
C11 C 0.0726(5) 0.9846(4) -0.1421(4) 0.0806(17) Uani 1 1 d . . . . .
H11A H -0.0012 0.9881 -0.1814 0.097 Uiso 1 1 calc R U . . .
H11B H 0.0475 1.0025 -0.0790 0.097 Uiso 1 1 calc R U . . .
C12 C 0.1528(8) 1.0780(6) -0.2043(8) 0.170(5) Uani 1 1 d . . . . .
H12A H 0.2158 1.0886 -0.1608 0.256 Uiso 1 1 calc R U . . .
H12B H 0.1073 1.1599 -0.2370 0.256 Uiso 1 1 calc R U . . .
H12C H 0.1909 1.0504 -0.2584 0.256 Uiso 1 1 calc R U . . .
C13 C 0.2852(3) 0.3856(3) 0.0438(3) 0.0327(8) Uani 1 1 d . . . . .
C14 C 0.3528(3) 0.2560(3) 0.0697(3) 0.0381(8) Uani 1 1 d . . . . .
C15 C 0.2924(4) 0.1470(4) 0.0779(3) 0.0490(10) Uani 1 1 d . . . . .
H15 H 0.2085 0.1526 0.0633 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3592(4) 0.0269(4) 0.1087(4) 0.0587(12) Uani 1 1 d . . . . .
C17 C 0.4824(5) 0.0158(5) 0.1295(4) 0.0724(14) Uani 1 1 d . . . . .
H17 H 0.5243 -0.0657 0.1524 0.087 Uiso 1 1 calc R U . . .
C18 C 0.5447(5) 0.1278(5) 0.1160(5) 0.0818(17) Uani 1 1 d . . . . .
H18 H 0.6298 0.1227 0.1259 0.098 Uiso 1 1 calc R U . . .
C19 C 0.4797(4) 0.2463(5) 0.0879(4) 0.0667(13) Uani 1 1 d . . . . .
H19 H 0.5208 0.3210 0.0809 0.080 Uiso 1 1 calc R U . . .
C20 C 0.0317(4) 0.1895(4) 0.3411(3) 0.0603(12) Uani 1 1 d . . . . .
C21 C 0.1108(5) 0.1832(6) 0.4329(4) 0.0801(16) Uani 1 1 d . . . . .
H21A H 0.0846 0.1124 0.4967 0.096 Uiso 1 1 calc R U . . .
H21B H 0.0984 0.2644 0.4454 0.096 Uiso 1 1 calc R U . . .
C22 C 0.2483(4) 0.1613(5) 0.4100(3) 0.0656(13) Uani 1 1 d . . . . .
C23 C 0.2743(8) 0.0271(7) 0.4043(6) 0.136(3) Uani 1 1 d . . . . .
H23A H 0.2233 0.0177 0.3516 0.205 Uiso 1 1 calc R U . . .
H23B H 0.2560 -0.0392 0.4722 0.205 Uiso 1 1 calc R U . . .
H23C H 0.3602 0.0177 0.3854 0.205 Uiso 1 1 calc R U . . .
C24 C 0.3223(7) 0.1772(10) 0.4970(5) 0.159(4) Uani 1 1 d . . . . .
H24A H 0.4094 0.1678 0.4823 0.239 Uiso 1 1 calc R U . . .
H24B H 0.3005 0.1114 0.5642 0.239 Uiso 1 1 calc R U . . .
H24C H 0.3036 0.2624 0.4995 0.239 Uiso 1 1 calc R U . . .
C25 C 0.2780(4) 0.2674(4) 0.3034(3) 0.0519(10) Uani 1 1 d . . . . .
H25 H 0.3563 0.3019 0.2910 0.062 Uiso 1 1 calc R U . . .
C26 C 0.1964(3) 0.3111(3) 0.2290(3) 0.0373(8) Uani 1 1 d . . . . .
C27 C 0.2117(3) 0.4128(3) 0.1208(3) 0.0339(8) Uani 1 1 d . . . . .
C28 C 0.1496(3) 0.5367(3) 0.0987(3) 0.0318(8) Uani 1 1 d . . . . .
C29 C 0.0871(3) 0.5619(3) 0.1911(3) 0.0340(8) Uani 1 1 d . . . . .
C30 C -0.0378(4) 0.5452(4) 0.2158(3) 0.0460(9) Uani 1 1 d . . . . .
H30 H -0.0878 0.5219 0.1722 0.055 Uiso 1 1 calc R U . . .
C31 C -0.0886(4) 0.5629(4) 0.3046(3) 0.0544(11) Uani 1 1 d . . . . .
H31 H -0.1724 0.5495 0.3215 0.065 Uiso 1 1 calc R U . . .
C32 C -0.0171(4) 0.6000(4) 0.3684(3) 0.0551(11) Uani 1 1 d . . . . .
H32 H -0.0518 0.6130 0.4280 0.066 Uiso 1 1 calc R U . . .
C33 C 0.1059(4) 0.6177(4) 0.3431(3) 0.0540(11) Uani 1 1 d . . . . .
C34 C 0.1600(4) 0.5979(4) 0.2554(3) 0.0453(9) Uani 1 1 d . . . . .
H34 H 0.2444 0.6087 0.2402 0.054 Uiso 1 1 calc R U . . .
Cl1 Cl 0.28062(15) -0.11203(13) 0.12550(17) 0.1056(6) Uani 1 1 d . . . . .
Cl2 Cl 0.19772(17) 0.6628(2) 0.42459(13) 0.1135(7) Uani 1 1 d . . . . .
N1 N 0.2472(3) 0.6781(3) -0.1863(2) 0.0391(7) Uani 1 1 d . . . . .
H1 H 0.2161 0.7560 -0.2184 0.047 Uiso 1 1 calc R U . . .
O1 O -0.0028(3) 0.7809(3) 0.0212(3) 0.0804(11) Uani 1 1 d . . . . .
O2 O 0.1334(3) 0.8551(2) -0.1115(2) 0.0543(8) Uani 1 1 d . . . . .
O3 O -0.0684(3) 0.1467(3) 0.3488(3) 0.0765(10) Uani 1 1 d . . . . .
O4 O 0.0770(2) 0.2608(2) 0.24238(19) 0.0439(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.378(5) . ?
C1 C2 1.391(5) . ?
C1 C6 1.403(5) . ?
C2 C3 1.369(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(5) . ?
C7 C13 1.392(5) . ?
C7 C8 1.421(5) . ?
C8 N1 1.373(4) . ?
C8 C9 1.400(5) . ?
C9 C28 1.394(5) . ?
C9 C10 1.498(5) . ?
C10 O1 1.190(4) . ?
C10 O2 1.325(4) . ?
C11 C12 1.384(8) . ?
C11 O2 1.452(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C27 1.392(5) . ?
C13 C14 1.490(5) . ?
C14 C15 1.365(5) . ?
C14 C19 1.394(6) . ?
C15 C16 1.396(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.361(6) . ?
C16 Cl1 1.728(4) . ?
C17 C18 1.387(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O3 1.190(5) . ?
C20 O4 1.362(5) . ?
C20 C21 1.519(7) . ?
C21 C22 1.526(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.517(9) . ?
C22 C25 1.518(6) . ?
C22 C24 1.522(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.303(5) . ?
C25 H25 0.9300 . ?
C26 O4 1.410(4) . ?
C26 C27 1.488(5) . ?
C27 C28 1.416(5) . ?
C28 C29 1.503(5) . ?
C29 C34 1.375(5) . ?
C29 C30 1.381(5) . ?
C30 C31 1.374(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.368(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.363(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.383(6) . ?
C33 Cl2 1.736(4) . ?
C34 H34 0.9300 . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 128.8(4) . . ?
N1 C1 C6 108.9(3) . . ?
C2 C1 C6 122.3(3) . . ?
C3 C2 C1 117.2(4) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.8(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.7(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 117.9(4) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 106.6(3) . . ?
C5 C6 C7 134.1(3) . . ?
C13 C7 C8 119.8(3) . . ?
C13 C7 C6 133.8(3) . . ?
C8 C7 C6 106.3(3) . . ?
N1 C8 C9 129.9(3) . . ?
N1 C8 C7 108.4(3) . . ?
C9 C8 C7 121.7(3) . . ?
C28 C9 C8 117.9(3) . . ?
C28 C9 C10 120.5(3) . . ?
C8 C9 C10 121.6(3) . . ?
O1 C10 O2 122.8(3) . . ?
O1 C10 C9 124.9(3) . . ?
O2 C10 C9 112.3(3) . . ?
C12 C11 O2 109.9(4) . . ?
C12 C11 H11A 109.7 . . ?
O2 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
O2 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C27 C13 C7 118.8(3) . . ?
C27 C13 C14 120.4(3) . . ?
C7 C13 C14 120.8(3) . . ?
C15 C14 C19 119.8(3) . . ?
C15 C14 C13 121.3(3) . . ?
C19 C14 C13 118.9(3) . . ?
C14 C15 C16 118.6(4) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 122.0(4) . . ?
C17 C16 Cl1 119.6(3) . . ?
C15 C16 Cl1 118.4(4) . . ?
C16 C17 C18 119.1(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C14 120.9(4) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
O3 C20 O4 118.4(4) . . ?
O3 C20 C21 125.8(4) . . ?
O4 C20 C21 115.6(4) . . ?
C20 C21 C22 111.5(4) . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C25 110.1(5) . . ?
C23 C22 C24 111.1(6) . . ?
C25 C22 C24 110.4(5) . . ?
C23 C22 C21 111.0(5) . . ?
C25 C22 C21 105.9(4) . . ?
C24 C22 C21 108.2(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C22 121.5(4) . . ?
C26 C25 H25 119.2 . . ?
C22 C25 H25 119.2 . . ?
C25 C26 O4 121.8(3) . . ?
C25 C26 C27 127.9(4) . . ?
O4 C26 C27 110.3(3) . . ?
C13 C27 C28 121.3(3) . . ?
C13 C27 C26 120.3(3) . . ?
C28 C27 C26 118.4(3) . . ?
C9 C28 C27 120.5(3) . . ?
C9 C28 C29 122.4(3) . . ?
C27 C28 C29 116.9(3) . . ?
C34 C29 C30 119.4(3) . . ?
C34 C29 C28 117.7(3) . . ?
C30 C29 C28 122.8(3) . . ?
C31 C30 C29 120.3(4) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 120.6(4) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C33 C32 C31 118.8(4) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C34 121.7(4) . . ?
C32 C33 Cl2 119.1(3) . . ?
C34 C33 Cl2 119.2(4) . . ?
C29 C34 C33 119.1(4) . . ?
C29 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C8 N1 C1 109.7(3) . . ?
C8 N1 H1 125.1 . . ?
C1 N1 H1 125.1 . . ?
C10 O2 C11 116.7(3) . . ?
C20 O4 C26 120.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.24 2.720(4) 115.0 .
N1 H1 O3 0.86 2.34 3.016(4) 135.9 2_565

_refine_diff_density_max         1.021
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 2078846'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H30 Cl N3 O5'
_chemical_formula_sum            'C33 H30 Cl N3 O5'
_chemical_formula_weight         584.05

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   8.6348(3)
_cell_length_b                   17.8206(7)
_cell_length_c                   18.8901(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.7464(13)
_cell_angle_gamma                90
_cell_volume                     2896.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.13

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27001
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5683
_reflns_number_gt                3986
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+1.1801P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5683
_refine_ls_number_parameters     383
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7097(2) 0.55054(11) 0.52970(10) 0.0395(5) Uani 1 1 d . . . . .
C2 C 0.6225(3) 0.51633(13) 0.57941(12) 0.0498(5) Uani 1 1 d . . . . .
H2 H 0.6034 0.4650 0.5781 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5658(3) 0.56107(14) 0.63054(13) 0.0584(6) Uani 1 1 d . . . . .
H3 H 0.5087 0.5394 0.6648 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5919(3) 0.63843(14) 0.63225(12) 0.0552(6) Uani 1 1 d . . . . .
H4 H 0.5552 0.6671 0.6684 0.066 Uiso 1 1 calc R U . . .
C5 C 0.6714(2) 0.67266(12) 0.58092(11) 0.0458(5) Uani 1 1 d . . . . .
H5 H 0.6856 0.7244 0.5814 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7304(2) 0.62883(11) 0.52819(10) 0.0370(5) Uani 1 1 d . . . . .
C7 C 0.8165(2) 0.64448(10) 0.46808(10) 0.0359(4) Uani 1 1 d . . . . .
C8 C 0.8484(2) 0.57773(11) 0.43790(10) 0.0370(4) Uani 1 1 d . . . . .
C9 C 0.9413(2) 0.56658(10) 0.37530(10) 0.0362(4) Uani 1 1 d . . . . .
H9 H 1.0447 0.5479 0.3919 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8601(2) 0.50847(11) 0.32641(11) 0.0412(5) Uani 1 1 d . . . . .
C11 C 0.8314(3) 0.37593(12) 0.31186(14) 0.0545(6) Uani 1 1 d . . . . .
H11A H 0.8392 0.3800 0.2611 0.065 Uiso 1 1 calc R U . . .
H11B H 0.7224 0.3733 0.3206 0.065 Uiso 1 1 calc R U . . .
C12 C 0.9155(4) 0.30774(13) 0.34067(15) 0.0742(8) Uani 1 1 d . . . . .
H12A H 1.0220 0.3099 0.3297 0.111 Uiso 1 1 calc R U . . .
H12B H 0.8673 0.2637 0.3196 0.111 Uiso 1 1 calc R U . . .
H12C H 0.9113 0.3059 0.3913 0.111 Uiso 1 1 calc R U . . .
C13 C 0.8579(2) 0.71981(10) 0.44041(10) 0.0362(4) Uani 1 1 d . . . . .
H13 H 0.9032 0.7487 0.4812 0.043 Uiso 1 1 calc R U . . .
C14 C 0.7183(2) 0.76396(11) 0.40887(11) 0.0394(5) Uani 1 1 d . U . . .
C15 C 0.7098(3) 0.84059(12) 0.42205(12) 0.0487(5) Uani 1 1 d . U . . .
H15 H 0.7877 0.8629 0.4519 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5897(3) 0.88483(14) 0.39238(14) 0.0604(6) Uani 1 1 d . U . . .
C17 C 0.5849(4) 0.96777(16) 0.4064(2) 0.1015(11) Uani 1 1 d . . . . .
H17A H 0.6560 0.9797 0.4466 0.152 Uiso 1 1 calc R U . . .
H17B H 0.4816 0.9820 0.4161 0.152 Uiso 1 1 calc R U . . .
H17C H 0.6142 0.9945 0.3655 0.152 Uiso 1 1 calc R U . . .
C18 C 0.4759(3) 0.85042(16) 0.34847(15) 0.0673(7) Uani 1 1 d . U . . .
H18 H 0.3954 0.8792 0.3269 0.081 Uiso 1 1 calc R U . . .
C19 C 0.4788(3) 0.77433(15) 0.33575(14) 0.0614(6) Uani 1 1 d . U . . .
H19 H 0.3995 0.7521 0.3066 0.074 Uiso 1 1 calc R U . . .
C20 C 0.5994(2) 0.73083(13) 0.36623(12) 0.0491(5) Uani 1 1 d . U . . .
H20 H 0.6005 0.6794 0.3580 0.059 Uiso 1 1 calc R U . . .
C21 C 0.9920(2) 0.78115(11) 0.34299(11) 0.0388(5) Uani 1 1 d . . . . .
C22 C 1.0323(3) 0.91707(13) 0.34258(16) 0.0689(7) Uani 1 1 d . . . . .
H22A H 1.1076 0.9268 0.3090 0.103 Uiso 1 1 calc R U . . .
H22B H 1.0399 0.9550 0.3788 0.103 Uiso 1 1 calc R U . . .
H22C H 0.9299 0.9178 0.3186 0.103 Uiso 1 1 calc R U . . .
C23 C 1.1626(3) 0.83978(13) 0.43655(13) 0.0506(6) Uani 1 1 d . . . . .
C24 C 1.3375(3) 0.76534(16) 0.51587(14) 0.0669(7) Uani 1 1 d . . . . .
H24A H 1.3609 0.7139 0.5274 0.100 Uiso 1 1 calc R U . . .
H24B H 1.3103 0.7912 0.5576 0.100 Uiso 1 1 calc R U . . .
H24C H 1.4269 0.7888 0.4984 0.100 Uiso 1 1 calc R U . . .
C25 C 1.1399(2) 0.70213(11) 0.43682(10) 0.0381(5) Uani 1 1 d . . . . .
C26 C 0.9922(2) 0.70965(10) 0.38733(10) 0.0346(4) Uani 1 1 d . . . . .
C27 C 0.9588(2) 0.64170(10) 0.33617(10) 0.0361(4) Uani 1 1 d . . . . .
H27 H 0.8571 0.6517 0.3110 0.043 Uiso 1 1 calc R U . . .
C28 C 1.0721(2) 0.63435(10) 0.27877(10) 0.0379(5) Uani 1 1 d . . . . .
C29 C 1.0219(3) 0.64440(12) 0.20765(11) 0.0465(5) Uani 1 1 d . . . . .
H29 H 0.9183 0.6563 0.1954 0.056 Uiso 1 1 calc R U . . .
C30 C 1.1222(3) 0.63718(12) 0.15470(11) 0.0525(6) Uani 1 1 d . . . . .
H30 H 1.0858 0.6440 0.1074 0.063 Uiso 1 1 calc R U . . .
C31 C 1.2756(3) 0.61999(11) 0.17211(11) 0.0488(6) Uani 1 1 d . . . . .
C32 C 1.3282(3) 0.60769(14) 0.24095(13) 0.0610(6) Uani 1 1 d . . . . .
H32 H 1.4315 0.5946 0.2526 0.073 Uiso 1 1 calc R U . . .
C33 C 1.2265(3) 0.61488(14) 0.29373(12) 0.0564(6) Uani 1 1 d . . . . .
H33 H 1.2633 0.6063 0.3407 0.068 Uiso 1 1 calc R U . . .
Cl1 Cl 1.40510(9) 0.61406(4) 0.10592(4) 0.0754(2) Uani 1 1 d . . . . .
N1 N 0.7844(2) 0.52026(9) 0.47472(8) 0.0417(4) Uani 1 1 d . . . . .
H1 H 0.7901 0.4733 0.4650 0.050 Uiso 1 1 calc R U . . .
N2 N 1.0624(2) 0.84284(9) 0.37528(10) 0.0467(4) Uani 1 1 d . . . . .
N3 N 1.2066(2) 0.76862(10) 0.46105(9) 0.0455(4) Uani 1 1 d . . . . .
O1 O 0.7660(2) 0.52072(9) 0.27771(9) 0.0628(5) Uani 1 1 d . . . . .
O2 O 0.90505(17) 0.44015(8) 0.34855(8) 0.0492(4) Uani 1 1 d . . . . .
O3 O 0.92285(18) 0.78613(8) 0.28499(8) 0.0494(4) Uani 1 1 d . . . . .
O4 O 1.2138(2) 0.89554(9) 0.46565(11) 0.0746(5) Uani 1 1 d . . . . .
O5 O 1.19028(17) 0.64244(8) 0.45900(8) 0.0493(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.377(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.435(3) . ?
C7 C8 1.357(3) . ?
C7 C13 1.495(3) . ?
C8 N1 1.379(2) . ?
C8 C9 1.496(3) . ?
C9 C10 1.520(3) . ?
C9 C27 1.543(3) . ?
C9 H9 0.9800 . ?
C10 O1 1.196(2) . ?
C10 O2 1.334(2) . ?
C11 O2 1.457(2) . ?
C11 C12 1.495(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.520(3) . ?
C13 C26 1.604(3) . ?
C13 H13 0.9800 . ?
C14 C20 1.384(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C16 C18 1.376(4) . ?
C16 C17 1.503(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.378(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O3 1.207(2) . ?
C21 N2 1.374(3) . ?
C21 C26 1.525(3) . ?
C22 N2 1.474(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O4 1.202(3) . ?
C23 N2 1.387(3) . ?
C23 N3 1.392(3) . ?
C24 N3 1.470(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.211(2) . ?
C25 N3 1.379(3) . ?
C25 C26 1.524(3) . ?
C26 C27 1.561(3) . ?
C27 C28 1.525(3) . ?
C27 H27 0.9800 . ?
C28 C33 1.384(3) . ?
C28 C29 1.389(3) . ?
C29 C30 1.382(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.359(3) . ?
C31 Cl1 1.748(2) . ?
C32 C33 1.388(3) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 130.56(19) . . ?
N1 C1 C6 107.76(17) . . ?
C2 C1 C6 121.65(19) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.08(19) . . ?
C5 C6 C7 134.42(19) . . ?
C1 C6 C7 106.49(17) . . ?
C8 C7 C6 107.36(17) . . ?
C8 C7 C13 125.27(17) . . ?
C6 C7 C13 127.31(17) . . ?
C7 C8 N1 109.60(17) . . ?
C7 C8 C9 126.10(17) . . ?
N1 C8 C9 124.29(17) . . ?
C8 C9 C10 108.69(16) . . ?
C8 C9 C27 110.10(15) . . ?
C10 C9 C27 111.03(16) . . ?
C8 C9 H9 109.0 . . ?
C10 C9 H9 109.0 . . ?
C27 C9 H9 109.0 . . ?
O1 C10 O2 124.68(19) . . ?
O1 C10 C9 126.35(19) . . ?
O2 C10 C9 108.89(17) . . ?
O2 C11 C12 106.58(19) . . ?
O2 C11 H11A 110.4 . . ?
C12 C11 H11A 110.4 . . ?
O2 C11 H11B 110.4 . . ?
C12 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C14 113.37(16) . . ?
C7 C13 C26 108.88(15) . . ?
C14 C13 C26 113.85(15) . . ?
C7 C13 H13 106.8 . . ?
C14 C13 H13 106.8 . . ?
C26 C13 H13 106.8 . . ?
C20 C14 C15 118.39(19) . . ?
C20 C14 C13 122.26(18) . . ?
C15 C14 C13 119.33(18) . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C18 C16 C15 117.6(2) . . ?
C18 C16 C17 121.1(2) . . ?
C15 C16 C17 121.3(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 121.4(2) . . ?
C16 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C14 C20 C19 120.0(2) . . ?
C14 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
O3 C21 N2 120.77(18) . . ?
O3 C21 C26 122.54(18) . . ?
N2 C21 C26 116.39(17) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N2 122.0(2) . . ?
O4 C23 N3 121.4(2) . . ?
N2 C23 N3 116.58(19) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 N3 120.80(18) . . ?
O5 C25 C26 123.23(18) . . ?
N3 C25 C26 115.69(17) . . ?
C25 C26 C21 111.90(16) . . ?
C25 C26 C27 114.45(15) . . ?
C21 C26 C27 108.44(15) . . ?
C25 C26 C13 103.77(15) . . ?
C21 C26 C13 106.33(15) . . ?
C27 C26 C13 111.62(15) . . ?
C28 C27 C9 111.12(15) . . ?
C28 C27 C26 114.23(15) . . ?
C9 C27 C26 113.38(15) . . ?
C28 C27 H27 105.8 . . ?
C9 C27 H27 105.8 . . ?
C26 C27 H27 105.8 . . ?
C33 C28 C29 116.6(2) . . ?
C33 C28 C27 122.70(18) . . ?
C29 C28 C27 120.63(19) . . ?
C30 C29 C28 121.6(2) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C31 C30 C29 119.8(2) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C32 C31 C30 120.3(2) . . ?
C32 C31 Cl1 119.4(2) . . ?
C30 C31 Cl1 120.24(17) . . ?
C31 C32 C33 119.4(2) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C28 C33 C32 122.2(2) . . ?
C28 C33 H33 118.9 . . ?
C32 C33 H33 118.9 . . ?
C1 N1 C8 108.75(16) . . ?
C1 N1 H1 125.6 . . ?
C8 N1 H1 125.6 . . ?
C21 N2 C23 124.13(18) . . ?
C21 N2 C22 118.41(19) . . ?
C23 N2 C22 117.46(19) . . ?
C25 N3 C23 125.28(18) . . ?
C25 N3 C24 118.38(18) . . ?
C23 N3 C24 116.32(18) . . ?
C10 O2 C11 117.61(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
N1 H1 O2 0.86 2.56 3.036(2) 116.3 .
N1 H1 O5 0.86 2.51 3.159(2) 132.8 3_766

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_3o
_database_code_depnum_ccdc_archive 'CCDC 2078849'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H31 N3 O8'
_chemical_formula_sum            'C34 H31 N3 O8'
_chemical_formula_weight         609.62

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   13.3152(19)
_cell_length_b                   11.0682(15)
_cell_length_c                   20.681
_cell_angle_alpha                90.000(4)
_cell_angle_beta                 96.176(4)
_cell_angle_gamma                90
_cell_volume                     3030.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7763
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.02

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6561
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23239
_diffrn_reflns_av_unetI/netI     0.1334
_diffrn_reflns_av_R_equivalents  0.2259
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.090
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5934
_reflns_number_gt                3480
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+7.6362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0141(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5934
_refine_ls_number_parameters     421
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1741
_refine_ls_R_factor_gt           0.1208
_refine_ls_wR_factor_ref         0.2476
_refine_ls_wR_factor_gt          0.2225
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2778(5) -0.2042(6) -0.0368(3) 0.0578(15) Uani 1 1 d . . . . .
C2 C 0.3015(5) -0.2957(7) -0.0778(3) 0.076(2) Uani 1 1 d . . . . .
H2 H 0.2913 -0.2854 -0.1227 0.091 Uiso 1 1 calc R U . . .
C3 C 0.3400(7) -0.4012(8) -0.0519(4) 0.099(3) Uani 1 1 d . . . . .
H3 H 0.3569 -0.4633 -0.0790 0.119 Uiso 1 1 calc R U . . .
C4 C 0.3541(7) -0.4160(7) 0.0161(4) 0.099(3) Uani 1 1 d . . . . .
H4 H 0.3801 -0.4884 0.0335 0.118 Uiso 1 1 calc R U . . .
C5 C 0.3305(6) -0.3263(6) 0.0572(3) 0.080(2) Uani 1 1 d . . . . .
H5 H 0.3399 -0.3375 0.1020 0.096 Uiso 1 1 calc R U . . .
C6 C 0.2922(5) -0.2177(5) 0.0309(3) 0.0532(14) Uani 1 1 d . . . . .
C7 C 0.2600(4) -0.1063(5) 0.0580(2) 0.0464(13) Uani 1 1 d . . . . .
C8 C 0.2301(4) -0.0308(5) 0.0081(2) 0.0454(13) Uani 1 1 d . . . . .
C9 C 0.1922(4) 0.0959(5) 0.0126(2) 0.0496(14) Uani 1 1 d . . . . .
H9 H 0.1224 0.1000 -0.0079 0.060 Uiso 1 1 calc R U . . .
C10 C 0.2578(5) 0.1826(7) -0.0226(3) 0.0685(19) Uani 1 1 d . . . . .
C11 C 0.2968(7) 0.2513(8) -0.1247(4) 0.106(2) Uani 1 1 d . U . . .
H11A H 0.3663 0.2248 -0.1242 0.127 Uiso 0.571(11) 1 calc R U P A 1
H11B H 0.2951 0.3341 -0.1094 0.127 Uiso 0.571(11) 1 calc R U P A 1
H11C H 0.2686 0.3320 -0.1239 0.127 Uiso 0.429(11) 1 calc R U P A 2
H11D H 0.2911 0.2249 -0.1697 0.127 Uiso 0.429(11) 1 calc R U P A 2
C12 C 0.2295(12) 0.2332(15) -0.2001(6) 0.112(4) Uani 0.571(11) 1 d . U P A 1
H12A H 0.2247 0.1487 -0.2106 0.168 Uiso 0.571(11) 1 calc R U P A 1
H12B H 0.2635 0.2746 -0.2323 0.168 Uiso 0.571(11) 1 calc R U P A 1
H12C H 0.1630 0.2661 -0.1995 0.168 Uiso 0.571(11) 1 calc R U P A 1
C12' C 0.4221(16) 0.257(2) -0.0953(10) 0.117(4) Uani 0.429(11) 1 d . U P A 2
H12D H 0.4293 0.2963 -0.0537 0.175 Uiso 0.429(11) 1 calc R U P A 2
H12E H 0.4587 0.3017 -0.1250 0.175 Uiso 0.429(11) 1 calc R U P A 2
H12F H 0.4486 0.1765 -0.0908 0.175 Uiso 0.429(11) 1 calc R U P A 2
C13 C 0.2627(4) -0.0702(5) 0.1280(2) 0.0459(13) Uani 1 1 d . . . . .
H13 H 0.2406 -0.1405 0.1516 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3691(4) -0.0400(5) 0.1573(2) 0.0443(12) Uani 1 1 d . . . . .
C15 C 0.4058(4) -0.0914(5) 0.2163(2) 0.0532(14) Uani 1 1 d . . . . .
H15 H 0.3646 -0.1411 0.2383 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5035(5) -0.0685(7) 0.2420(3) 0.0679(19) Uani 1 1 d . . . . .
H16 H 0.5289 -0.1021 0.2817 0.081 Uiso 1 1 calc R U . . .
C17 C 0.5626(4) 0.0039(7) 0.2086(3) 0.0638(17) Uani 1 1 d . . . . .
C18 C 0.5288(4) 0.0566(6) 0.1501(3) 0.0603(16) Uani 1 1 d . . . . .
H18 H 0.5707 0.1058 0.1283 0.072 Uiso 1 1 calc R U . . .
C19 C 0.4314(4) 0.0340(5) 0.1249(3) 0.0530(14) Uani 1 1 d . . . . .
H19 H 0.4065 0.0687 0.0855 0.064 Uiso 1 1 calc R U . . .
C20 C 0.0779(4) -0.0293(5) 0.1241(2) 0.0432(12) Uani 1 1 d . . . . .
C21 C 0.0411(5) -0.0972(5) 0.1802(2) 0.0559(15) Uani 1 1 d . . . . .
H21A H 0.0782 -0.1724 0.1863 0.067 Uiso 1 1 calc R U . . .
H21B H -0.0297 -0.1169 0.1695 0.067 Uiso 1 1 calc R U . . .
C22 C 0.0535(4) -0.0260(6) 0.2433(2) 0.0521(14) Uani 1 1 d . . . . .
C23 C -0.0114(5) 0.0889(7) 0.2373(3) 0.0733(19) Uani 1 1 d . . . . .
H23A H -0.0808 0.0673 0.2255 0.110 Uiso 1 1 calc R U . . .
H23B H 0.0111 0.1404 0.2044 0.110 Uiso 1 1 calc R U . . .
H23C H -0.0052 0.1307 0.2782 0.110 Uiso 1 1 calc R U . . .
C24 C 0.0238(5) -0.1043(7) 0.2985(3) 0.081(2) Uani 1 1 d . . . . .
H24A H -0.0456 -0.1281 0.2894 0.121 Uiso 1 1 calc R U . . .
H24B H 0.0325 -0.0594 0.3384 0.121 Uiso 1 1 calc R U . . .
H24C H 0.0658 -0.1750 0.3025 0.121 Uiso 1 1 calc R U . . .
C25 C 0.1642(4) 0.0097(5) 0.2572(2) 0.0506(14) Uani 1 1 d . . . . .
H25A H 0.1733 0.0556 0.2973 0.061 Uiso 1 1 calc R U . . .
H25B H 0.2050 -0.0628 0.2633 0.061 Uiso 1 1 calc R U . . .
C26 C 0.2004(4) 0.0832(5) 0.2039(2) 0.0422(12) Uani 1 1 d . . . . .
C27 C 0.1812(4) 0.0337(5) 0.1336(2) 0.0414(12) Uani 1 1 d . . . . .
C28 C 0.1954(4) 0.1373(5) 0.0841(2) 0.0437(12) Uani 1 1 d . . . . .
H28 H 0.2644 0.1669 0.0957 0.052 Uiso 1 1 calc R U . . .
C29 C 0.1282(4) 0.2475(5) 0.0871(2) 0.0451(12) Uani 1 1 d . . . . .
C30 C 0.1719(4) 0.3568(5) 0.1079(3) 0.0577(16) Uani 1 1 d . . . . .
H30 H 0.2405 0.3585 0.1223 0.069 Uiso 1 1 calc R U . . .
C31 C 0.1178(5) 0.4618(6) 0.1080(3) 0.0660(18) Uani 1 1 d . . . . .
H31 H 0.1488 0.5336 0.1225 0.079 Uiso 1 1 calc R U . . .
C32 C 0.0179(5) 0.4588(5) 0.0865(3) 0.0551(15) Uani 1 1 d . . . . .
C33 C -0.0290(4) 0.3537(6) 0.0649(3) 0.0574(15) Uani 1 1 d . . . . .
H33 H -0.0976 0.3538 0.0506 0.069 Uiso 1 1 calc R U . . .
C34 C 0.0253(4) 0.2488(5) 0.0645(3) 0.0511(14) Uani 1 1 d . . . . .
H34 H -0.0064 0.1780 0.0490 0.061 Uiso 1 1 calc R U . . .
N1 N 0.2395(4) -0.0888(5) -0.0497(2) 0.0581(13) Uani 1 1 d . . . . .
H1 H 0.2241 -0.0585 -0.0877 0.070 Uiso 1 1 calc R U . . .
N2 N 0.6683(4) 0.0212(9) 0.2339(3) 0.114(3) Uani 1 1 d . . . . .
N3 N -0.0413(5) 0.5715(6) 0.0863(3) 0.0790(17) Uani 1 1 d . . . . .
O1 O 0.3191(4) 0.2507(7) 0.0021(3) 0.119(2) Uani 1 1 d . . . . .
O2 O 0.2361(4) 0.1685(4) -0.0870(2) 0.0901(15) Uani 1 1 d . U . . .
O3 O 0.6956(4) -0.0177(9) 0.2886(3) 0.156(4) Uani 1 1 d . . . . .
O4 O 0.7224(4) 0.0726(9) 0.1988(3) 0.155(4) Uani 1 1 d . . . . .
O5 O 0.0285(3) -0.0264(4) 0.07167(17) 0.0610(11) Uani 1 1 d . . . . .
O6 O 0.2471(3) 0.1775(4) 0.21512(17) 0.0569(10) Uani 1 1 d . . . . .
O7 O -0.1268(4) 0.5716(5) 0.0594(3) 0.1006(17) Uani 1 1 d . . . . .
O8 O -0.0015(6) 0.6592(6) 0.1112(4) 0.168(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(9) . ?
C1 N1 1.390(8) . ?
C1 C6 1.400(7) . ?
C2 C3 1.363(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(8) . ?
C7 C8 1.354(7) . ?
C7 C13 1.500(7) . ?
C8 N1 1.373(6) . ?
C8 C9 1.496(8) . ?
C9 C10 1.533(8) . ?
C9 C28 1.545(7) . ?
C9 H9 0.9800 . ?
C10 O1 1.186(9) . ?
C10 O2 1.341(8) . ?
C11 O2 1.496(8) . ?
C11 C12' 1.71(2) . ?
C11 C12 1.726(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13 C14 1.518(7) . ?
C13 C27 1.594(7) . ?
C13 H13 0.9800 . ?
C14 C15 1.386(7) . ?
C14 C19 1.388(7) . ?
C15 C16 1.376(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(8) . ?
C17 N2 1.460(8) . ?
C18 C19 1.367(7) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O5 1.207(6) . ?
C20 C21 1.506(7) . ?
C20 C27 1.537(7) . ?
C21 C22 1.519(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C24 1.518(8) . ?
C22 C25 1.523(7) . ?
C22 C23 1.536(9) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.492(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O6 1.224(6) . ?
C26 C27 1.548(6) . ?
C27 C28 1.562(7) . ?
C28 C29 1.519(7) . ?
C28 H28 0.9800 . ?
C29 C30 1.390(7) . ?
C29 C34 1.400(7) . ?
C30 C31 1.367(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.357(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.372(8) . ?
C32 N3 1.476(8) . ?
C33 C34 1.368(8) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 H1 0.8600 . ?
N2 O4 1.219(8) . ?
N2 O3 1.227(8) . ?
N3 O8 1.195(8) . ?
N3 O7 1.213(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 131.3(6) . . ?
C2 C1 C6 121.4(6) . . ?
N1 C1 C6 107.3(5) . . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.8(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 121.5(8) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.9(6) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.2(6) . . ?
C5 C6 C7 134.4(5) . . ?
C1 C6 C7 106.4(5) . . ?
C8 C7 C6 107.9(4) . . ?
C8 C7 C13 123.2(5) . . ?
C6 C7 C13 128.8(5) . . ?
C7 C8 N1 109.1(5) . . ?
C7 C8 C9 127.2(5) . . ?
N1 C8 C9 123.7(5) . . ?
C8 C9 C10 110.1(5) . . ?
C8 C9 C28 111.3(4) . . ?
C10 C9 C28 108.1(5) . . ?
C8 C9 H9 109.1 . . ?
C10 C9 H9 109.1 . . ?
C28 C9 H9 109.1 . . ?
O1 C10 O2 124.6(6) . . ?
O1 C10 C9 126.5(6) . . ?
O2 C10 C9 109.0(6) . . ?
O2 C11 C12' 113.5(9) . . ?
O2 C11 C12 98.2(8) . . ?
O2 C11 H11A 112.1 . . ?
C12 C11 H11A 112.1 . . ?
O2 C11 H11B 112.1 . . ?
C12 C11 H11B 112.1 . . ?
H11A C11 H11B 109.8 . . ?
O2 C11 H11C 108.9 . . ?
C12' C11 H11C 108.9 . . ?
O2 C11 H11D 108.9 . . ?
C12' C11 H11D 108.9 . . ?
H11C C11 H11D 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12' H12D 109.5 . . ?
C11 C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11 C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C7 C13 C14 111.6(4) . . ?
C7 C13 C27 108.5(4) . . ?
C14 C13 C27 115.2(4) . . ?
C7 C13 H13 107.1 . . ?
C14 C13 H13 107.1 . . ?
C27 C13 H13 107.1 . . ?
C15 C14 C19 119.7(5) . . ?
C15 C14 C13 119.1(5) . . ?
C19 C14 C13 121.2(4) . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 119.1(5) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 122.9(5) . . ?
C16 C17 N2 118.8(6) . . ?
C18 C17 N2 118.1(6) . . ?
C19 C18 C17 117.7(6) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C14 121.0(5) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
O5 C20 C21 120.9(5) . . ?
O5 C20 C27 119.8(4) . . ?
C21 C20 C27 119.2(4) . . ?
C20 C21 C22 112.9(5) . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C24 C22 C21 109.7(5) . . ?
C24 C22 C25 109.4(5) . . ?
C21 C22 C25 108.1(4) . . ?
C24 C22 C23 110.1(5) . . ?
C21 C22 C23 110.5(5) . . ?
C25 C22 C23 109.0(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C22 112.7(4) . . ?
C26 C25 H25A 109.1 . . ?
C22 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C22 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
O6 C26 C25 121.5(4) . . ?
O6 C26 C27 120.7(5) . . ?
C25 C26 C27 117.8(4) . . ?
C20 C27 C26 109.7(4) . . ?
C20 C27 C28 114.8(4) . . ?
C26 C27 C28 109.6(4) . . ?
C20 C27 C13 105.7(4) . . ?
C26 C27 C13 106.2(4) . . ?
C28 C27 C13 110.5(4) . . ?
C29 C28 C9 108.8(4) . . ?
C29 C28 C27 116.7(4) . . ?
C9 C28 C27 114.7(4) . . ?
C29 C28 H28 105.2 . . ?
C9 C28 H28 105.2 . . ?
C27 C28 H28 105.2 . . ?
C30 C29 C34 117.2(5) . . ?
C30 C29 C28 118.8(5) . . ?
C34 C29 C28 123.7(5) . . ?
C31 C30 C29 122.5(5) . . ?
C31 C30 H30 118.8 . . ?
C29 C30 H30 118.8 . . ?
C32 C31 C30 118.4(6) . . ?
C32 C31 H31 120.8 . . ?
C30 C31 H31 120.8 . . ?
C31 C32 C33 121.6(6) . . ?
C31 C32 N3 119.0(6) . . ?
C33 C32 N3 119.4(5) . . ?
C34 C33 C32 120.0(5) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C29 120.3(5) . . ?
C33 C34 H34 119.9 . . ?
C29 C34 H34 119.9 . . ?
C8 N1 C1 109.2(4) . . ?
C8 N1 H1 125.4 . . ?
C1 N1 H1 125.4 . . ?
O4 N2 O3 125.2(6) . . ?
O4 N2 C17 117.2(6) . . ?
O3 N2 C17 117.6(7) . . ?
O8 N3 O7 123.3(7) . . ?
O8 N3 C32 118.2(6) . . ?
O7 N3 C32 118.5(6) . . ?
C10 O2 C11 112.0(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 179.0(7) . . . . ?
C6 C1 C2 C3 -0.2(10) . . . . ?
C1 C2 C3 C4 0.6(12) . . . . ?
C2 C3 C4 C5 -0.4(14) . . . . ?
C3 C4 C5 C6 -0.4(13) . . . . ?
C4 C5 C6 C1 0.8(11) . . . . ?
C4 C5 C6 C7 -179.8(7) . . . . ?
C2 C1 C6 C5 -0.5(10) . . . . ?
N1 C1 C6 C5 -179.9(6) . . . . ?
C2 C1 C6 C7 179.9(6) . . . . ?
N1 C1 C6 C7 0.6(6) . . . . ?
C5 C6 C7 C8 179.5(7) . . . . ?
C1 C6 C7 C8 -1.1(6) . . . . ?
C5 C6 C7 C13 2.9(11) . . . . ?
C1 C6 C7 C13 -177.6(5) . . . . ?
C6 C7 C8 N1 1.1(6) . . . . ?
C13 C7 C8 N1 178.0(5) . . . . ?
C6 C7 C8 C9 -178.9(5) . . . . ?
C13 C7 C8 C9 -2.1(9) . . . . ?
C7 C8 C9 C10 122.7(6) . . . . ?
N1 C8 C9 C10 -57.4(7) . . . . ?
C7 C8 C9 C28 2.8(8) . . . . ?
N1 C8 C9 C28 -177.2(5) . . . . ?
C8 C9 C10 O1 -105.2(8) . . . . ?
C28 C9 C10 O1 16.6(9) . . . . ?
C8 C9 C10 O2 74.0(6) . . . . ?
C28 C9 C10 O2 -164.3(5) . . . . ?
C8 C7 C13 C14 -101.3(6) . . . . ?
C6 C7 C13 C14 74.8(7) . . . . ?
C8 C7 C13 C27 26.6(7) . . . . ?
C6 C7 C13 C27 -157.3(5) . . . . ?
C7 C13 C14 C15 -130.8(5) . . . . ?
C27 C13 C14 C15 104.9(6) . . . . ?
C7 C13 C14 C19 46.5(7) . . . . ?
C27 C13 C14 C19 -77.7(6) . . . . ?
C19 C14 C15 C16 0.0(9) . . . . ?
C13 C14 C15 C16 177.4(5) . . . . ?
C14 C15 C16 C17 -0.4(10) . . . . ?
C15 C16 C17 C18 0.4(11) . . . . ?
C15 C16 C17 N2 -175.8(7) . . . . ?
C16 C17 C18 C19 -0.1(10) . . . . ?
N2 C17 C18 C19 176.2(7) . . . . ?
C17 C18 C19 C14 -0.3(9) . . . . ?
C15 C14 C19 C18 0.3(9) . . . . ?
C13 C14 C19 C18 -177.0(5) . . . . ?
O5 C20 C21 C22 -134.9(6) . . . . ?
C27 C20 C21 C22 47.0(7) . . . . ?
C20 C21 C22 C24 -174.9(5) . . . . ?
C20 C21 C22 C25 -55.7(6) . . . . ?
C20 C21 C22 C23 63.5(6) . . . . ?
C24 C22 C25 C26 177.9(5) . . . . ?
C21 C22 C25 C26 58.5(6) . . . . ?
C23 C22 C25 C26 -61.7(6) . . . . ?
C22 C25 C26 O6 131.1(5) . . . . ?
C22 C25 C26 C27 -51.5(6) . . . . ?
O5 C20 C27 C26 147.1(5) . . . . ?
C21 C20 C27 C26 -34.8(6) . . . . ?
O5 C20 C27 C28 23.2(7) . . . . ?
C21 C20 C27 C28 -158.6(5) . . . . ?
O5 C20 C27 C13 -98.9(6) . . . . ?
C21 C20 C27 C13 79.3(5) . . . . ?
O6 C26 C27 C20 -145.7(5) . . . . ?
C25 C26 C27 C20 36.9(6) . . . . ?
O6 C26 C27 C28 -18.9(6) . . . . ?
C25 C26 C27 C28 163.7(4) . . . . ?
O6 C26 C27 C13 100.5(5) . . . . ?
C25 C26 C27 C13 -76.8(5) . . . . ?
C7 C13 C27 C20 73.6(5) . . . . ?
C14 C13 C27 C20 -160.5(4) . . . . ?
C7 C13 C27 C26 -169.9(4) . . . . ?
C14 C13 C27 C26 -44.1(5) . . . . ?
C7 C13 C27 C28 -51.1(5) . . . . ?
C14 C13 C27 C28 74.7(5) . . . . ?
C8 C9 C28 C29 -162.8(4) . . . . ?
C10 C9 C28 C29 76.2(5) . . . . ?
C8 C9 C28 C27 -30.1(6) . . . . ?
C10 C9 C28 C27 -151.1(4) . . . . ?
C20 C27 C28 C29 65.0(6) . . . . ?
C26 C27 C28 C29 -58.8(5) . . . . ?
C13 C27 C28 C29 -175.6(4) . . . . ?
C20 C27 C28 C9 -63.8(6) . . . . ?
C26 C27 C28 C9 172.3(4) . . . . ?
C13 C27 C28 C9 55.6(5) . . . . ?
C9 C28 C29 C30 -116.2(5) . . . . ?
C27 C28 C29 C30 112.2(6) . . . . ?
C9 C28 C29 C34 57.7(6) . . . . ?
C27 C28 C29 C34 -74.0(6) . . . . ?
C34 C29 C30 C31 1.4(9) . . . . ?
C28 C29 C30 C31 175.6(5) . . . . ?
C29 C30 C31 C32 -0.5(10) . . . . ?
C30 C31 C32 C33 -0.1(9) . . . . ?
C30 C31 C32 N3 -179.9(6) . . . . ?
C31 C32 C33 C34 -0.3(9) . . . . ?
N3 C32 C33 C34 179.5(5) . . . . ?
C32 C33 C34 C29 1.2(9) . . . . ?
C30 C29 C34 C33 -1.7(8) . . . . ?
C28 C29 C34 C33 -175.7(5) . . . . ?
C7 C8 N1 C1 -0.8(6) . . . . ?
C9 C8 N1 C1 179.2(5) . . . . ?
C2 C1 N1 C8 -179.2(6) . . . . ?
C6 C1 N1 C8 0.1(6) . . . . ?
C16 C17 N2 O4 170.2(9) . . . . ?
C18 C17 N2 O4 -6.2(13) . . . . ?
C16 C17 N2 O3 -9.3(13) . . . . ?
C18 C17 N2 O3 174.2(9) . . . . ?
C31 C32 N3 O8 -7.5(10) . . . . ?
C33 C32 N3 O8 172.7(8) . . . . ?
C31 C32 N3 O7 170.6(6) . . . . ?
C33 C32 N3 O7 -9.2(9) . . . . ?
O1 C10 O2 C11 -1.3(10) . . . . ?
C9 C10 O2 C11 179.5(5) . . . . ?
C12' C11 O2 C10 44.8(12) . . . . ?
C12 C11 O2 C10 -166.9(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.52 2.949(7) 112.0 .
N1 H1 O4 0.86 2.48 3.183(7) 139.4 3_655

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2078851'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H26 N4 O7'
_chemical_formula_sum            'C33 H26 N4 O7'
_chemical_formula_weight         590.58

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9596(5)
_cell_length_b                   9.3710(6)
_cell_length_c                   19.8144(11)
_cell_angle_alpha                99.2210(18)
_cell_angle_beta                 100.1718(17)
_cell_angle_gamma                96.4144(19)
_cell_volume                     1599.44(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8145
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.81

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22802
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.125
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6250
_reflns_number_gt                4106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+0.6870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6250
_refine_ls_number_parameters     402
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7141(3) 0.4112(2) 0.48976(11) 0.0442(5) Uani 1 1 d . . . . .
C2 C 0.7793(3) 0.4788(3) 0.55727(11) 0.0530(6) Uani 1 1 d . . . . .
H2 H 0.8755 0.5351 0.5678 0.064 Uiso 1 1 calc R U . . .
C3 C 0.6973(3) 0.4601(3) 0.60853(12) 0.0563(6) Uani 1 1 d . . . . .
H3 H 0.7391 0.5043 0.6545 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5540(3) 0.3768(3) 0.59290(11) 0.0547(6) Uani 1 1 d . . . . .
H4 H 0.5002 0.3680 0.6285 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4885(3) 0.3062(2) 0.52537(11) 0.0471(5) Uani 1 1 d . . . . .
H5 H 0.3926 0.2493 0.5153 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5703(2) 0.3229(2) 0.47349(10) 0.0405(5) Uani 1 1 d . . . . .
C7 C 0.5425(2) 0.2698(2) 0.39801(10) 0.0382(5) Uani 1 1 d . . . . .
C8 C 0.6779(2) 0.3408(2) 0.37788(11) 0.0404(5) Uani 1 1 d . . . . .
C9 C 0.6902(2) 0.3218(2) 0.30526(11) 0.0421(5) Uani 1 1 d . . . . .
C10 C 0.8217(3) 0.4077(3) 0.28518(11) 0.0488(6) Uani 1 1 d . . . . .
C11 C 0.8903(4) 0.6205(4) 0.2406(2) 0.0903(9) Uani 1 1 d . U . . .
H11A H 0.9350 0.5600 0.2073 0.108 Uiso 1 1 calc R U . . .
H11B H 0.9719 0.6751 0.2776 0.108 Uiso 1 1 calc R U . . .
C12 C 0.8008(5) 0.7200(6) 0.2063(3) 0.1573(19) Uani 1 1 d . U . . .
H12A H 0.7276 0.6648 0.1668 0.236 Uiso 1 1 calc R U . . .
H12B H 0.8683 0.7892 0.1908 0.236 Uiso 1 1 calc R U . . .
H12C H 0.7480 0.7709 0.2386 0.236 Uiso 1 1 calc R U . . .
C13 C 0.4307(2) 0.1797(2) 0.35199(10) 0.0391(5) Uani 1 1 d . . . . .
C14 C 0.2947(2) 0.0996(2) 0.37022(10) 0.0393(5) Uani 1 1 d . . . . .
C15 C 0.1482(3) 0.1354(3) 0.35285(11) 0.0483(6) Uani 1 1 d . . . . .
H15 H 0.1334 0.2139 0.3303 0.058 Uiso 1 1 calc R U . . .
C16 C 0.0243(3) 0.0554(3) 0.36883(13) 0.0574(6) Uani 1 1 d . . . . .
H16 H -0.0727 0.0817 0.3570 0.069 Uiso 1 1 calc R U . . .
C17 C 0.0407(3) -0.0624(3) 0.40178(13) 0.0571(7) Uani 1 1 d . . . . .
C18 C -0.0954(4) -0.1489(4) 0.41893(17) 0.0881(10) Uani 1 1 d . . . . .
H18A H -0.0742 -0.2460 0.4222 0.132 Uiso 1 1 calc R U . . .
H18B H -0.1837 -0.1535 0.3829 0.132 Uiso 1 1 calc R U . . .
H18C H -0.1148 -0.1022 0.4627 0.132 Uiso 1 1 calc R U . . .
C19 C 0.1874(3) -0.0960(3) 0.41977(14) 0.0645(7) Uani 1 1 d . . . . .
H19 H 0.2020 -0.1741 0.4427 0.077 Uiso 1 1 calc R U . . .
C20 C 0.3126(3) -0.0168(3) 0.40467(13) 0.0545(6) Uani 1 1 d . . . . .
H20 H 0.4097 -0.0418 0.4177 0.065 Uiso 1 1 calc R U . . .
C21 C 0.3053(3) 0.1789(3) 0.23016(12) 0.0552(6) Uani 1 1 d . . . . .
C22 C 0.0547(4) 0.0957(6) 0.1553(2) 0.1262(16) Uani 1 1 d . . . . .
H22A H -0.0194 0.0999 0.1849 0.189 Uiso 1 1 calc R U . . .
H22B H 0.0162 0.0210 0.1148 0.189 Uiso 1 1 calc R U . . .
H22C H 0.0732 0.1884 0.1411 0.189 Uiso 1 1 calc R U . . .
C23 C 0.2148(3) -0.0841(4) 0.19337(14) 0.0743(9) Uani 1 1 d . . . . .
C24 C 0.3607(5) -0.2750(3) 0.22326(17) 0.0984(12) Uani 1 1 d . . . . .
H24A H 0.4631 -0.2858 0.2439 0.148 Uiso 1 1 calc R U . . .
H24B H 0.3375 -0.3231 0.1753 0.148 Uiso 1 1 calc R U . . .
H24C H 0.2897 -0.3180 0.2479 0.148 Uiso 1 1 calc R U . . .
C25 C 0.4689(3) -0.0178(3) 0.26406(12) 0.0541(6) Uani 1 1 d . . . . .
C26 C 0.4474(2) 0.1446(2) 0.27521(11) 0.0433(5) Uani 1 1 d . . . . .
C27 C 0.5845(2) 0.2308(2) 0.25692(11) 0.0448(5) Uani 1 1 d . . . . .
C28 C 0.5949(3) 0.2108(3) 0.18146(12) 0.0545(6) Uani 1 1 d . . . . .
C29 C 0.6551(3) 0.0925(4) 0.15114(14) 0.0719(8) Uani 1 1 d . . . . .
H29 H 0.6849 0.0223 0.1770 0.086 Uiso 1 1 calc R U . . .
C30 C 0.6710(3) 0.0789(5) 0.08184(17) 0.0933(12) Uani 1 1 d . . . . .
H30 H 0.7133 0.0008 0.0613 0.112 Uiso 1 1 calc R U . . .
C31 C 0.6239(4) 0.1814(5) 0.04435(15) 0.0939(13) Uani 1 1 d . . . . .
C32 C 0.5628(4) 0.2968(5) 0.07276(17) 0.1001(12) Uani 1 1 d . . . . .
H32 H 0.5309 0.3650 0.0461 0.120 Uiso 1 1 calc R U . . .
C33 C 0.5482(4) 0.3125(4) 0.14199(14) 0.0807(9) Uani 1 1 d . . . . .
H33 H 0.5069 0.3918 0.1619 0.097 Uiso 1 1 calc R U . . .
N1 N 0.7779(2) 0.4209(2) 0.42933(9) 0.0469(5) Uani 1 1 d . . . . .
N2 N 0.1986(2) 0.0620(3) 0.19366(10) 0.0708(7) Uani 1 1 d . . . . .
N3 N 0.3479(3) -0.1171(2) 0.22734(11) 0.0646(6) Uani 1 1 d . . . . .
N4 N 0.6392(5) 0.1628(7) -0.02975(18) 0.1329(17) Uani 1 1 d . . . . .
O1 O 0.9423(2) 0.3689(2) 0.28218(12) 0.0832(6) Uani 1 1 d . . . . .
O2 O 0.7817(2) 0.5309(2) 0.26897(11) 0.0713(5) Uani 1 1 d . U . . .
O3 O 0.2882(2) 0.3042(3) 0.22824(10) 0.0744(6) Uani 1 1 d . . . . .
O4 O 0.1103(3) -0.1788(3) 0.16215(13) 0.1216(10) Uani 1 1 d . . . . .
O5 O 0.5868(3) -0.0545(2) 0.28982(11) 0.0808(6) Uani 1 1 d . . . . .
O6 O 0.5795(5) 0.2438(6) -0.06439(17) 0.192(2) Uani 1 1 d . . . . .
O7 O 0.7071(4) 0.0670(5) -0.05161(17) 0.174(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(3) . ?
C1 C6 1.406(3) . ?
C1 N1 1.426(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.466(3) . ?
C7 C13 1.338(3) . ?
C7 C8 1.466(3) . ?
C8 N1 1.299(3) . ?
C8 C9 1.447(3) . ?
C9 C27 1.334(3) . ?
C9 C10 1.500(3) . ?
C10 O1 1.186(3) . ?
C10 O2 1.318(3) . ?
C11 O2 1.459(3) . ?
C11 C12 1.467(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.489(3) . ?
C13 C26 1.541(3) . ?
C14 C20 1.386(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C19 1.385(4) . ?
C17 C18 1.507(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O3 1.206(3) . ?
C21 N2 1.380(3) . ?
C21 C26 1.517(3) . ?
C22 N2 1.471(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O4 1.216(3) . ?
C23 N3 1.356(4) . ?
C23 N2 1.392(4) . ?
C24 N3 1.487(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.201(3) . ?
C25 N3 1.360(3) . ?
C25 C26 1.541(3) . ?
C26 C27 1.524(3) . ?
C27 C28 1.498(3) . ?
C28 C33 1.381(4) . ?
C28 C29 1.384(4) . ?
C29 C30 1.392(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.364(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.354(6) . ?
C31 N4 1.483(4) . ?
C32 C33 1.387(4) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
N4 O7 1.206(7) . ?
N4 O6 1.209(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.6(2) . . ?
C2 C1 N1 126.4(2) . . ?
C6 C1 N1 112.07(18) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 C7 134.7(2) . . ?
C1 C6 C7 105.24(18) . . ?
C13 C7 C6 134.52(19) . . ?
C13 C7 C8 122.58(18) . . ?
C6 C7 C8 102.90(17) . . ?
N1 C8 C9 125.21(19) . . ?
N1 C8 C7 114.68(18) . . ?
C9 C8 C7 120.09(18) . . ?
C27 C9 C8 120.23(19) . . ?
C27 C9 C10 120.71(19) . . ?
C8 C9 C10 119.05(18) . . ?
O1 C10 O2 124.8(2) . . ?
O1 C10 C9 125.3(2) . . ?
O2 C10 C9 109.9(2) . . ?
O2 C11 C12 105.5(3) . . ?
O2 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
O2 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C14 124.66(18) . . ?
C7 C13 C26 118.84(18) . . ?
C14 C13 C26 116.32(17) . . ?
C20 C14 C15 118.1(2) . . ?
C20 C14 C13 119.56(19) . . ?
C15 C14 C13 122.38(19) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C19 117.3(2) . . ?
C16 C17 C18 121.2(3) . . ?
C19 C17 C18 121.5(3) . . ?
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 . . ?
C20 C19 C17 121.8(2) . . ?
C20 C19 H19 119.1 . . ?
C17 C19 H19 119.1 . . ?
C19 C20 C14 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C14 C20 H20 119.7 . . ?
O3 C21 N2 122.8(2) . . ?
O3 C21 C26 120.0(2) . . ?
N2 C21 C26 117.1(3) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N3 121.7(4) . . ?
O4 C23 N2 119.4(3) . . ?
N3 C23 N2 118.9(2) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 N3 121.8(3) . . ?
O5 C25 C26 120.4(2) . . ?
N3 C25 C26 117.7(2) . . ?
C21 C26 C27 106.66(18) . . ?
C21 C26 C25 115.0(2) . . ?
C27 C26 C25 107.85(18) . . ?
C21 C26 C13 108.01(17) . . ?
C27 C26 C13 115.68(17) . . ?
C25 C26 C13 103.97(17) . . ?
C9 C27 C28 120.88(19) . . ?
C9 C27 C26 122.13(18) . . ?
C28 C27 C26 116.98(18) . . ?
C33 C28 C29 119.4(3) . . ?
C33 C28 C27 120.2(2) . . ?
C29 C28 C27 120.4(2) . . ?
C28 C29 C30 119.8(3) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.3(3) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C32 C31 C30 121.8(3) . . ?
C32 C31 N4 120.0(5) . . ?
C30 C31 N4 118.2(5) . . ?
C31 C32 C33 119.4(4) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C28 C33 C32 120.3(3) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C8 N1 C1 105.08(17) . . ?
C21 N2 C23 124.7(2) . . ?
C21 N2 C22 117.0(3) . . ?
C23 N2 C22 118.2(3) . . ?
C23 N3 C25 125.2(3) . . ?
C23 N3 C24 116.5(3) . . ?
C25 N3 C24 118.3(3) . . ?
O7 N4 O6 124.6(4) . . ?
O7 N4 C31 118.3(6) . . ?
O6 N4 C31 117.1(6) . . ?
C10 O2 C11 117.2(2) . . ?

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.038


####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2078844'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H30 N4 O7'
_chemical_formula_sum            'C33 H30 N4 O7'
_chemical_formula_weight         594.61

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.1728(16)
_cell_length_b                   13.4083(18)
_cell_length_c                   22.278(3)
_cell_angle_alpha                86.724(4)
_cell_angle_beta                 89.748(4)
_cell_angle_gamma                78.705(4)
_cell_volume                     3559.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6334
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.76

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5936
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47241
_diffrn_reflns_av_unetI/netI     0.2330
_diffrn_reflns_av_R_equivalents  0.1627
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             13916
_reflns_number_gt                6248
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1178P)²+2.8640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13916
_refine_ls_number_parameters     801
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2259
_refine_ls_R_factor_gt           0.0987
_refine_ls_wR_factor_ref         0.2709
_refine_ls_wR_factor_gt          0.2202
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6461(4) 0.4724(3) 0.4025(2) 0.0228(11) Uani 1 1 d . . . . .
C2 C 0.5441(4) 0.5335(4) 0.4192(2) 0.0286(12) Uani 1 1 d . . . . .
H2 H 0.4882 0.5052 0.4381 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5308(4) 0.6361(4) 0.4067(2) 0.0313(12) Uani 1 1 d . . . . .
H3 H 0.4648 0.6784 0.4178 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6141(4) 0.6794(4) 0.3774(2) 0.0288(12) Uani 1 1 d . . . . .
H4 H 0.6019 0.7494 0.3688 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7145(4) 0.6188(3) 0.3610(2) 0.0266(11) Uani 1 1 d . . . . .
H5 H 0.7695 0.6478 0.3417 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7313(3) 0.5148(3) 0.3738(2) 0.0186(10) Uani 1 1 d . . . . .
C7 C 0.8226(3) 0.4292(3) 0.3659(2) 0.0199(11) Uani 1 1 d . . . . .
C8 C 0.7882(4) 0.3443(3) 0.3869(2) 0.0219(11) Uani 1 1 d . . . . .
C9 C 0.8539(3) 0.2384(3) 0.3914(2) 0.0220(11) Uani 1 1 d . . . . .
H9 H 0.8676 0.2159 0.4338 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7953(4) 0.1653(4) 0.3612(2) 0.0295(12) Uani 1 1 d . . . . .
C11 C 0.7541(6) 0.0002(4) 0.3671(3) 0.0622(19) Uani 1 1 d . . . . .
H11A H 0.7992 -0.0201 0.3322 0.075 Uiso 1 1 calc R U . . .
H11B H 0.6773 0.0247 0.3538 0.075 Uiso 1 1 calc R U . . .
C12 C 0.7595(7) -0.0874(5) 0.4101(3) 0.075(2) Uani 1 1 d . . . . .
H12A H 0.8339 -0.1067 0.4265 0.112 Uiso 1 1 calc R U . . .
H12B H 0.7409 -0.1434 0.3900 0.112 Uiso 1 1 calc R U . . .
H12C H 0.7073 -0.0695 0.4420 0.112 Uiso 1 1 calc R U . . .
C13 C 0.9381(4) 0.4319(3) 0.3419(2) 0.0219(11) Uani 1 1 d . . . . .
H13 H 0.9631 0.4889 0.3597 0.026 Uiso 1 1 calc R U . . .
C14 C 0.9428(4) 0.4496(4) 0.2739(2) 0.0257(11) Uani 1 1 d . . . . .
C15 C 1.0123(4) 0.5119(4) 0.2492(2) 0.0331(13) Uani 1 1 d . . . . .
H15 H 1.0507 0.5460 0.2746 0.040 Uiso 1 1 calc R U . . .
C16 C 1.0257(5) 0.5242(4) 0.1878(3) 0.0456(15) Uani 1 1 d . . . . .
H16 H 1.0719 0.5671 0.1726 0.055 Uiso 1 1 calc R U . . .
C17 C 0.9712(6) 0.4738(5) 0.1490(3) 0.0545(17) Uani 1 1 d . . . . .
C18 C 0.9862(7) 0.4821(6) 0.0808(3) 0.092(3) Uani 1 1 d . . . . .
H18A H 0.9996 0.4153 0.0656 0.138 Uiso 1 1 calc R U . . .
H18B H 1.0488 0.5140 0.0715 0.138 Uiso 1 1 calc R U . . .
H18C H 0.9196 0.5224 0.0625 0.138 Uiso 1 1 calc R U . . .
C19 C 0.8982(5) 0.4145(4) 0.1735(2) 0.0433(14) Uani 1 1 d . . . . .
H19 H 0.8579 0.3827 0.1478 0.052 Uiso 1 1 calc R U . . .
C20 C 0.8840(4) 0.4017(4) 0.2344(2) 0.0301(12) Uani 1 1 d . . . . .
H20 H 0.8351 0.3611 0.2494 0.036 Uiso 1 1 calc R U . . .
C21 C 1.0457(4) 0.3449(3) 0.4312(2) 0.0201(11) Uani 1 1 d . . . . .
C22 C 1.1570(5) 0.4155(4) 0.5041(2) 0.0421(14) Uani 1 1 d . . . . .
H22A H 1.0881 0.4232 0.5261 0.063 Uiso 1 1 calc R U . . .
H22B H 1.1839 0.4783 0.5030 0.063 Uiso 1 1 calc R U . . .
H22C H 1.2117 0.3623 0.5236 0.063 Uiso 1 1 calc R U . . .
C23 C 1.2228(4) 0.3955(4) 0.4012(2) 0.0320(13) Uani 1 1 d . . . . .
C24 C 1.3028(5) 0.3692(5) 0.3012(3) 0.0557(17) Uani 1 1 d . . . . .
H24A H 1.3345 0.4279 0.3076 0.084 Uiso 1 1 calc R U . . .
H24B H 1.2743 0.3736 0.2608 0.084 Uiso 1 1 calc R U . . .
H24C H 1.3596 0.3087 0.3073 0.084 Uiso 1 1 calc R U . . .
C25 C 1.1253(4) 0.3172(4) 0.3268(2) 0.0253(11) Uani 1 1 d . . . . .
C26 C 1.0212(4) 0.3291(3) 0.3663(2) 0.0214(11) Uani 1 1 d . . . . .
C27 C 0.9673(3) 0.2348(3) 0.3588(2) 0.0192(10) Uani 1 1 d . . . . .
H27 H 0.9500 0.2357 0.3159 0.023 Uiso 1 1 calc R U . . .
C28 C 1.0470(4) 0.1327(3) 0.3734(2) 0.0247(11) Uani 1 1 d . . . . .
C29 C 1.0714(4) 0.0963(4) 0.4326(2) 0.0298(12) Uani 1 1 d . . . . .
H29 H 1.0387 0.1338 0.4641 0.036 Uiso 1 1 calc R U . . .
C30 C 1.1460(4) 0.0021(4) 0.4447(2) 0.0320(13) Uani 1 1 d . . . . .
H30 H 1.1618 -0.0244 0.4840 0.038 Uiso 1 1 calc R U . . .
C31 C 1.1939(4) -0.0484(4) 0.3968(2) 0.0318(13) Uani 1 1 d . . . . .
C32 C 1.1692(4) -0.0171(4) 0.3377(2) 0.0328(13) Uani 1 1 d . . . . .
H32 H 1.2018 -0.0558 0.3066 0.039 Uiso 1 1 calc R U . . .
C33 C 1.0937(4) 0.0743(3) 0.3258(2) 0.0301(12) Uani 1 1 d . . . . .
H33 H 1.0741 0.0967 0.2863 0.036 Uiso 1 1 calc R U . . .
C34 C 0.0692(4) 0.7567(4) 0.2772(2) 0.0304(12) Uani 1 1 d . . . . .
C35 C -0.0165(4) 0.7560(4) 0.3188(2) 0.0390(14) Uani 1 1 d . . . . .
H35 H -0.0903 0.7859 0.3092 0.047 Uiso 1 1 calc R U . . .
C36 C 0.0123(4) 0.7094(4) 0.3747(3) 0.0401(14) Uani 1 1 d . . . . .
H36 H -0.0432 0.7083 0.4035 0.048 Uiso 1 1 calc R U . . .
C37 C 0.1230(5) 0.6635(4) 0.3894(2) 0.0407(14) Uani 1 1 d . . . . .
H37 H 0.1397 0.6335 0.4277 0.049 Uiso 1 1 calc R U . . .
C38 C 0.2074(4) 0.6620(4) 0.3484(2) 0.0315(12) Uani 1 1 d . . . . .
H38 H 0.2804 0.6300 0.3584 0.038 Uiso 1 1 calc R U . . .
C39 C 0.1822(4) 0.7092(4) 0.2910(2) 0.0286(12) Uani 1 1 d . . . . .
C40 C 0.2456(4) 0.7279(4) 0.2385(2) 0.0271(12) Uani 1 1 d . . . . .
C41 C 0.1725(4) 0.7812(4) 0.1965(2) 0.0284(12) Uani 1 1 d . . . . .
C42 C 0.2008(4) 0.8207(4) 0.1362(2) 0.0271(12) Uani 1 1 d . . . . .
H42 H 0.1831 0.8953 0.1345 0.033 Uiso 1 1 calc R U . . .
C43 C 0.1347(4) 0.7828(5) 0.0876(2) 0.0386(14) Uani 1 1 d . . . . .
C44 C -0.0255(6) 0.8278(7) 0.0221(4) 0.090(3) Uani 1 1 d . . . . .
H44A H -0.0614 0.8882 -0.0017 0.108 Uiso 1 1 calc R U . . .
H44B H 0.0179 0.7806 -0.0045 0.108 Uiso 1 1 calc R U . . .
C45 C -0.1089(7) 0.7808(8) 0.0536(4) 0.113(3) Uani 1 1 d . . . . .
H45A H -0.0725 0.7194 0.0752 0.170 Uiso 1 1 calc R U . . .
H45B H -0.1608 0.7649 0.0250 0.170 Uiso 1 1 calc R U . . .
H45C H -0.1486 0.8271 0.0812 0.170 Uiso 1 1 calc R U . . .
C46 C 0.3715(4) 0.7013(4) 0.2311(2) 0.0286(12) Uani 1 1 d . . . . .
H46 H 0.4048 0.7167 0.2686 0.034 Uiso 1 1 calc R U . . .
C47 C 0.4169(4) 0.5908(3) 0.2215(2) 0.0205(11) Uani 1 1 d . . . . .
C48 C 0.5107(4) 0.5407(4) 0.2545(2) 0.0274(12) Uani 1 1 d . . . . .
H48 H 0.5430 0.5758 0.2822 0.033 Uiso 1 1 calc R U . . .
C49 C 0.5564(4) 0.4392(4) 0.2464(2) 0.0325(12) Uani 1 1 d . . . . .
H49 H 0.6174 0.4065 0.2698 0.039 Uiso 1 1 calc R U . . .
C50 C 0.5126(4) 0.3860(4) 0.2041(2) 0.0331(13) Uani 1 1 d . . . . .
C51 C 0.5644(5) 0.2752(4) 0.1944(3) 0.0592(18) Uani 1 1 d . . . . .
H51A H 0.6191 0.2724 0.1630 0.089 Uiso 1 1 calc R U . . .
H51B H 0.5069 0.2400 0.1831 0.089 Uiso 1 1 calc R U . . .
H51C H 0.5999 0.2435 0.2309 0.089 Uiso 1 1 calc R U . . .
C52 C 0.4191(4) 0.4358(4) 0.1715(2) 0.0332(13) Uani 1 1 d . . . . .
H52 H 0.3879 0.4013 0.1430 0.040 Uiso 1 1 calc R U . . .
C53 C 0.3719(4) 0.5360(4) 0.1808(2) 0.0294(12) Uani 1 1 d . . . . .
H53 H 0.3082 0.5673 0.1590 0.035 Uiso 1 1 calc R U . . .
C54 C 0.3994(4) 0.8776(4) 0.2071(2) 0.0273(12) Uani 1 1 d . . . . .
C55 C 0.4845(4) 0.9796(4) 0.2749(2) 0.0413(14) Uani 1 1 d . . . . .
H55A H 0.5141 0.9593 0.3146 0.062 Uiso 1 1 calc R U . . .
H55B H 0.4072 1.0123 0.2776 0.062 Uiso 1 1 calc R U . . .
H55C H 0.5262 1.0262 0.2558 0.062 Uiso 1 1 calc R U . . .
C56 C 0.5978(4) 0.8292(4) 0.2350(2) 0.0283(12) Uani 1 1 d . . . . .
C57 C 0.7226(4) 0.6858(4) 0.1908(2) 0.0404(14) Uani 1 1 d . . . . .
H57A H 0.7175 0.6179 0.1814 0.061 Uiso 1 1 calc R U . . .
H57B H 0.7658 0.6834 0.2269 0.061 Uiso 1 1 calc R U . . .
H57C H 0.7583 0.7171 0.1583 0.061 Uiso 1 1 calc R U . . .
C58 C 0.5253(4) 0.7302(4) 0.1617(2) 0.0247(11) Uani 1 1 d . . . . .
C59 C 0.4059(4) 0.7779(3) 0.17857(19) 0.0234(11) Uani 1 1 d . . . . .
C60 C 0.3283(4) 0.7842(4) 0.1224(2) 0.0254(11) Uani 1 1 d . . . . .
H60 H 0.3362 0.7142 0.1100 0.030 Uiso 1 1 calc R U . . .
C61 C 0.3581(4) 0.8456(3) 0.0680(2) 0.0239(11) Uani 1 1 d . . . . .
C62 C 0.3324(4) 0.9508(4) 0.0623(2) 0.0303(12) Uani 1 1 d . . . . .
H62 H 0.3015 0.9868 0.0948 0.036 Uiso 1 1 calc R U . . .
C63 C 0.3512(4) 1.0040(4) 0.0095(2) 0.0337(13) Uani 1 1 d . . . . .
H63 H 0.3323 1.0748 0.0060 0.040 Uiso 1 1 calc R U . . .
C64 C 0.3989(4) 0.9493(4) -0.0380(2) 0.0350(13) Uani 1 1 d . . . . .
C65 C 0.4282(4) 0.8443(4) -0.0346(2) 0.0382(13) Uani 1 1 d . . . . .
H65 H 0.4613 0.8089 -0.0668 0.046 Uiso 1 1 calc R U . . .
C66 C 0.4062(4) 0.7944(4) 0.0184(2) 0.0354(13) Uani 1 1 d . . . . .
H66 H 0.4240 0.7236 0.0214 0.042 Uiso 1 1 calc R U . . .
N1 N 0.6810(3) 0.3689(3) 0.40978(18) 0.0281(10) Uani 1 1 d . . . . .
H1 H 0.6430 0.3266 0.4257 0.034 Uiso 1 1 calc R U . . .
N2 N 1.2100(3) 0.3650(3) 0.34437(19) 0.0323(10) Uani 1 1 d . . . . .
N3 N 1.1376(3) 0.3890(3) 0.44246(18) 0.0299(10) Uani 1 1 d . . . . .
N4 N 1.2824(4) -0.1398(3) 0.4087(3) 0.0473(13) Uani 1 1 d . . . . .
N5 N 0.0650(3) 0.7977(3) 0.21866(18) 0.0329(10) Uani 1 1 d . . . . .
H5A H 0.0057 0.8283 0.1995 0.040 Uiso 1 1 calc R U . . .
N6 N 0.4935(3) 0.8904(3) 0.23989(17) 0.0275(10) Uani 1 1 d . . . . .
N7 N 0.6085(3) 0.7463(3) 0.19955(18) 0.0266(10) Uani 1 1 d . . . . .
N8 N 0.4190(4) 1.0055(4) -0.0947(2) 0.0500(13) Uani 1 1 d . . . . .
O1 O 0.7566(3) 0.1797(3) 0.31108(18) 0.0531(11) Uani 1 1 d . . . . .
O2 O 0.7948(3) 0.0798(3) 0.39503(16) 0.0403(9) Uani 1 1 d . . . . .
O3 O 0.9875(3) 0.3263(2) 0.47251(14) 0.0289(8) Uani 1 1 d . . . . .
O4 O 1.3067(3) 0.4242(3) 0.41613(17) 0.0526(11) Uani 1 1 d . . . . .
O5 O 1.1320(3) 0.2752(3) 0.28042(16) 0.0367(9) Uani 1 1 d . . . . .
O6 O 1.3498(3) -0.1637(3) 0.3683(2) 0.0655(13) Uani 1 1 d . . . . .
O7 O 1.2834(4) -0.1854(3) 0.4584(2) 0.0661(13) Uani 1 1 d . . . . .
O8 O 0.1541(3) 0.6996(3) 0.06939(19) 0.0589(12) Uani 1 1 d . . . . .
O9 O 0.0486(3) 0.8554(3) 0.06930(19) 0.0655(13) Uani 1 1 d . . . . .
O10 O 0.3154(3) 0.9453(3) 0.20587(15) 0.0354(9) Uani 1 1 d . . . . .
O11 O 0.6781(3) 0.8504(3) 0.26097(16) 0.0418(9) Uani 1 1 d . . . . .
O12 O 0.5453(3) 0.6740(3) 0.12114(15) 0.0329(8) Uani 1 1 d . . . . .
O13 O 0.4631(5) 0.9559(4) -0.13618(19) 0.0823(16) Uani 1 1 d . . . . .
O14 O 0.3914(4) 1.0983(4) -0.09746(19) 0.0626(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.370(5) . ?
C1 C2 1.409(6) . ?
C1 C6 1.412(6) . ?
C2 C3 1.366(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.405(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.451(6) . ?
C7 C8 1.347(6) . ?
C7 C13 1.508(6) . ?
C8 N1 1.384(5) . ?
C8 C9 1.485(6) . ?
C9 C10 1.508(7) . ?
C9 C27 1.550(6) . ?
C9 H9 0.9800 . ?
C10 O1 1.204(6) . ?
C10 O2 1.337(6) . ?
C11 O2 1.434(6) . ?
C11 C12 1.463(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.522(6) . ?
C13 C26 1.610(6) . ?
C13 H13 0.9800 . ?
C14 C15 1.392(7) . ?
C14 C20 1.397(6) . ?
C15 C16 1.380(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(8) . ?
C16 H16 0.9300 . ?
C17 C19 1.394(8) . ?
C17 C18 1.531(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.372(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O3 1.202(5) . ?
C21 N3 1.394(6) . ?
C21 C26 1.514(6) . ?
C22 N3 1.469(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O4 1.215(6) . ?
C23 N2 1.371(6) . ?
C23 N3 1.395(6) . ?
C24 N2 1.487(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.201(5) . ?
C25 N2 1.385(6) . ?
C25 C26 1.527(7) . ?
C26 C27 1.550(6) . ?
C27 C28 1.534(6) . ?
C27 H27 0.9800 . ?
C28 C29 1.392(6) . ?
C28 C33 1.405(6) . ?
C29 C30 1.417(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.363(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.376(7) . ?
C31 N4 1.476(6) . ?
C32 C33 1.393(6) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 N5 1.384(6) . ?
C34 C35 1.393(7) . ?
C34 C39 1.425(7) . ?
C35 C36 1.376(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.399(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.369(7) . ?
C37 H37 0.9300 . ?
C38 C39 1.400(7) . ?
C38 H38 0.9300 . ?
C39 C40 1.435(7) . ?
C40 C41 1.365(6) . ?
C40 C46 1.515(6) . ?
C41 N5 1.377(6) . ?
C41 C42 1.480(6) . ?
C42 C43 1.520(7) . ?
C42 C60 1.568(6) . ?
C42 H42 0.9800 . ?
C43 O8 1.188(6) . ?
C43 O9 1.331(7) . ?
C44 C45 1.455(11) . ?
C44 O9 1.496(7) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 C47 1.503(6) . ?
C46 C59 1.621(6) . ?
C46 H46 0.9800 . ?
C47 C53 1.380(6) . ?
C47 C48 1.394(6) . ?
C48 C49 1.387(6) . ?
C48 H48 0.9300 . ?
C49 C50 1.382(7) . ?
C49 H49 0.9300 . ?
C50 C52 1.388(7) . ?
C50 C51 1.523(7) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 C53 1.381(7) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?
C54 O10 1.227(5) . ?
C54 N6 1.404(6) . ?
C54 C59 1.501(7) . ?
C55 N6 1.451(6) . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C56 O11 1.225(5) . ?
C56 N6 1.378(6) . ?
C56 N7 1.386(6) . ?
C57 N7 1.483(6) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 O12 1.204(5) . ?
C58 N7 1.377(6) . ?
C58 C59 1.523(6) . ?
C59 C60 1.559(6) . ?
C60 C61 1.509(6) . ?
C60 H60 0.9800 . ?
C61 C62 1.382(6) . ?
C61 C66 1.401(7) . ?
C62 C63 1.382(7) . ?
C62 H62 0.9300 . ?
C63 C64 1.382(7) . ?
C63 H63 0.9300 . ?
C64 C65 1.380(7) . ?
C64 N8 1.479(7) . ?
C65 C66 1.375(7) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
N1 H1 0.8600 . ?
N4 O6 1.230(6) . ?
N4 O7 1.233(6) . ?
N5 H5A 0.8600 . ?
N8 O14 1.222(6) . ?
N8 O13 1.229(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 129.3(4) . . ?
N1 C1 C6 109.1(4) . . ?
C2 C1 C6 121.6(4) . . ?
C3 C2 C1 117.3(4) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.8(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 C7 135.3(4) . . ?
C1 C6 C7 105.1(4) . . ?
C8 C7 C6 107.5(4) . . ?
C8 C7 C13 124.7(4) . . ?
C6 C7 C13 127.6(4) . . ?
C7 C8 N1 110.2(4) . . ?
C7 C8 C9 127.7(4) . . ?
N1 C8 C9 121.8(4) . . ?
C8 C9 C10 112.2(4) . . ?
C8 C9 C27 109.4(4) . . ?
C10 C9 C27 106.6(4) . . ?
C8 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C27 C9 H9 109.5 . . ?
O1 C10 O2 122.9(5) . . ?
O1 C10 C9 124.2(5) . . ?
O2 C10 C9 112.9(4) . . ?
O2 C11 C12 109.6(5) . . ?
O2 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
O2 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C14 114.3(4) . . ?
C7 C13 C26 108.0(3) . . ?
C14 C13 C26 112.6(4) . . ?
C7 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C26 C13 H13 107.2 . . ?
C15 C14 C20 117.7(4) . . ?
C15 C14 C13 119.5(4) . . ?
C20 C14 C13 122.7(4) . . ?
C16 C15 C14 121.6(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C17 C16 C15 120.6(5) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C19 117.9(5) . . ?
C16 C17 C18 122.7(6) . . ?
C19 C17 C18 119.5(6) . . ?
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 . . ?
C20 C19 C17 122.0(5) . . ?
C20 C19 H19 119.0 . . ?
C17 C19 H19 119.0 . . ?
C19 C20 C14 120.0(5) . . ?
C19 C20 H20 120.0 . . ?
C14 C20 H20 120.0 . . ?
O3 C21 N3 119.1(4) . . ?
O3 C21 C26 123.7(4) . . ?
N3 C21 C26 117.1(4) . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N2 121.6(5) . . ?
O4 C23 N3 120.5(5) . . ?
N2 C23 N3 117.8(4) . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 N2 120.3(4) . . ?
O5 C25 C26 122.7(5) . . ?
N2 C25 C26 116.7(4) . . ?
C21 C26 C25 112.9(4) . . ?
C21 C26 C27 113.0(4) . . ?
C25 C26 C27 107.5(4) . . ?
C21 C26 C13 105.6(3) . . ?
C25 C26 C13 106.8(3) . . ?
C27 C26 C13 110.8(3) . . ?
C28 C27 C26 113.9(3) . . ?
C28 C27 C9 110.8(4) . . ?
C26 C27 C9 114.7(3) . . ?
C28 C27 H27 105.5 . . ?
C26 C27 H27 105.5 . . ?
C9 C27 H27 105.5 . . ?
C29 C28 C33 119.9(4) . . ?
C29 C28 C27 121.2(4) . . ?
C33 C28 C27 118.9(4) . . ?
C28 C29 C30 120.0(5) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 117.5(5) . . ?
C31 C30 H30 121.2 . . ?
C29 C30 H30 121.2 . . ?
C30 C31 C32 124.4(4) . . ?
C30 C31 N4 118.2(5) . . ?
C32 C31 N4 117.4(5) . . ?
C31 C32 C33 118.0(5) . . ?
C31 C32 H32 121.0 . . ?
C33 C32 H32 121.0 . . ?
C32 C33 C28 120.1(5) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?
N5 C34 C35 130.0(5) . . ?
N5 C34 C39 108.3(4) . . ?
C35 C34 C39 121.8(5) . . ?
C36 C35 C34 117.5(5) . . ?
C36 C35 H35 121.3 . . ?
C34 C35 H35 121.3 . . ?
C35 C36 C37 121.6(5) . . ?
C35 C36 H36 119.2 . . ?
C37 C36 H36 119.2 . . ?
C38 C37 C36 121.4(5) . . ?
C38 C37 H37 119.3 . . ?
C36 C37 H37 119.3 . . ?
C37 C38 C39 119.1(5) . . ?
C37 C38 H38 120.5 . . ?
C39 C38 H38 120.5 . . ?
C38 C39 C34 118.7(4) . . ?
C38 C39 C40 135.5(4) . . ?
C34 C39 C40 105.7(4) . . ?
C41 C40 C39 107.6(4) . . ?
C41 C40 C46 124.8(4) . . ?
C39 C40 C46 127.4(4) . . ?
C40 C41 N5 110.2(4) . . ?
C40 C41 C42 126.7(4) . . ?
N5 C41 C42 123.1(4) . . ?
C41 C42 C43 110.8(4) . . ?
C41 C42 C60 111.1(4) . . ?
C43 C42 C60 107.4(4) . . ?
C41 C42 H42 109.2 . . ?
C43 C42 H42 109.2 . . ?
C60 C42 H42 109.2 . . ?
O8 C43 O9 124.3(5) . . ?
O8 C43 C42 125.5(5) . . ?
O9 C43 C42 110.2(5) . . ?
C45 C44 O9 106.6(7) . . ?
C45 C44 H44A 110.4 . . ?
O9 C44 H44A 110.4 . . ?
C45 C44 H44B 110.4 . . ?
O9 C44 H44B 110.4 . . ?
H44A C44 H44B 108.6 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 C40 114.5(4) . . ?
C47 C46 C59 113.4(4) . . ?
C40 C46 C59 107.9(4) . . ?
C47 C46 H46 106.9 . . ?
C40 C46 H46 106.9 . . ?
C59 C46 H46 106.9 . . ?
C53 C47 C48 117.7(4) . . ?
C53 C47 C46 123.4(4) . . ?
C48 C47 C46 118.9(4) . . ?
C49 C48 C47 120.8(4) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
C50 C49 C48 121.0(5) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 H49 119.5 . . ?
C49 C50 C52 118.2(5) . . ?
C49 C50 C51 121.0(5) . . ?
C52 C50 C51 120.9(5) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C53 C52 C50 120.7(5) . . ?
C53 C52 H52 119.6 . . ?
C50 C52 H52 119.6 . . ?
C47 C53 C52 121.6(4) . . ?
C47 C53 H53 119.2 . . ?
C52 C53 H53 119.2 . . ?
O10 C54 N6 118.9(4) . . ?
O10 C54 C59 123.7(4) . . ?
N6 C54 C59 117.3(4) . . ?
N6 C55 H55A 109.5 . . ?
N6 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
N6 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
O11 C56 N6 119.6(5) . . ?
O11 C56 N7 122.1(4) . . ?
N6 C56 N7 118.3(4) . . ?
N7 C57 H57A 109.5 . . ?
N7 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
N7 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
O12 C58 N7 121.5(4) . . ?
O12 C58 C59 122.1(4) . . ?
N7 C58 C59 116.0(4) . . ?
C54 C59 C58 112.2(4) . . ?
C54 C59 C60 114.0(4) . . ?
C58 C59 C60 109.1(4) . . ?
C54 C59 C46 105.2(4) . . ?
C58 C59 C46 105.1(3) . . ?
C60 C59 C46 110.7(4) . . ?
C61 C60 C59 116.1(4) . . ?
C61 C60 C42 108.7(4) . . ?
C59 C60 C42 113.6(4) . . ?
C61 C60 H60 105.9 . . ?
C59 C60 H60 105.9 . . ?
C42 C60 H60 105.9 . . ?
C62 C61 C66 117.3(4) . . ?
C62 C61 C60 123.5(4) . . ?
C66 C61 C60 118.9(4) . . ?
C63 C62 C61 121.8(5) . . ?
C63 C62 H62 119.1 . . ?
C61 C62 H62 119.1 . . ?
C62 C63 C64 118.2(5) . . ?
C62 C63 H63 120.9 . . ?
C64 C63 H63 120.9 . . ?
C65 C64 C63 122.7(5) . . ?
C65 C64 N8 118.7(5) . . ?
C63 C64 N8 118.6(5) . . ?
C66 C65 C64 117.1(5) . . ?
C66 C65 H65 121.4 . . ?
C64 C65 H65 121.4 . . ?
C65 C66 C61 122.8(5) . . ?
C65 C66 H66 118.6 . . ?
C61 C66 H66 118.6 . . ?
C1 N1 C8 108.0(4) . . ?
C1 N1 H1 126.0 . . ?
C8 N1 H1 126.0 . . ?
C23 N2 C25 124.7(4) . . ?
C23 N2 C24 117.5(4) . . ?
C25 N2 C24 117.2(4) . . ?
C21 N3 C23 124.0(4) . . ?
C21 N3 C22 118.6(4) . . ?
C23 N3 C22 116.6(4) . . ?
O6 N4 O7 125.2(5) . . ?
O6 N4 C31 117.2(5) . . ?
O7 N4 C31 117.6(5) . . ?
C41 N5 C34 108.1(4) . . ?
C41 N5 H5A 125.9 . . ?
C34 N5 H5A 125.9 . . ?
C56 N6 C54 123.2(4) . . ?
C56 N6 C55 117.7(4) . . ?
C54 N6 C55 118.6(4) . . ?
C58 N7 C56 123.6(4) . . ?
C58 N7 C57 117.0(4) . . ?
C56 N7 C57 117.8(4) . . ?
O14 N8 O13 124.0(5) . . ?
O14 N8 C64 118.2(5) . . ?
O13 N8 C64 117.9(5) . . ?
C10 O2 C11 116.8(4) . . ?
C43 O9 C44 116.0(5) . . ?

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.075


####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 2078848'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H33 N3 O7'
_chemical_formula_weight         595.63

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   8.8520(7)
_cell_length_b                   18.3198(15)
_cell_length_c                   18.4779(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.474(3)
_cell_angle_gamma                90
_cell_volume                     2982.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3292
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      20.18

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27845
_diffrn_reflns_av_unetI/netI     0.1515
_diffrn_reflns_av_R_equivalents  0.1304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5836
_reflns_number_gt                2417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+0.4877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5836
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2193
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1593
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7885(4) 0.4513(2) -0.0360(2) 0.0511(9) Uani 1 1 d . . . . .
C2 C 0.8763(4) 0.4872(2) -0.0827(2) 0.0700(11) Uani 1 1 d . . . . .
H2 H 0.8968 0.5368 -0.0776 0.084 Uiso 1 1 calc R U . . .
C3 C 0.9319(5) 0.4474(3) -0.1366(2) 0.0807(13) Uani 1 1 d . . . . .
H3 H 0.9913 0.4705 -0.1686 0.097 Uiso 1 1 calc R U . . .
C4 C 0.9025(5) 0.3731(3) -0.1450(2) 0.0760(12) Uani 1 1 d . . . . .
H4 H 0.9387 0.3480 -0.1835 0.091 Uiso 1 1 calc R U . . .
C5 C 0.8202(4) 0.3364(2) -0.0968(2) 0.0610(10) Uani 1 1 d . . . . .
H5 H 0.8028 0.2865 -0.1016 0.073 Uiso 1 1 calc R U . . .
C6 C 0.7633(4) 0.3761(2) -0.04061(18) 0.0462(9) Uani 1 1 d . . . . .
C7 C 0.6759(3) 0.35682(18) 0.01822(17) 0.0430(8) Uani 1 1 d . . . . .
C8 C 0.6475(3) 0.41905(19) 0.05360(17) 0.0427(8) Uani 1 1 d . . . . .
C9 C 0.5563(3) 0.42608(16) 0.11772(16) 0.0419(8) Uani 1 1 d . . . . .
H9 H 0.4565 0.4465 0.1014 0.050 Uiso 1 1 calc R U . . .
C10 C 0.6379(4) 0.4776(2) 0.1724(2) 0.0494(9) Uani 1 1 d . . . . .
C11 C 0.6732(4) 0.60384(19) 0.1998(2) 0.0684(11) Uani 1 1 d . . . . .
H11A H 0.7809 0.6042 0.1938 0.082 Uiso 1 1 calc R U . . .
H11B H 0.6603 0.5963 0.2508 0.082 Uiso 1 1 calc R U . . .
C12 C 0.6026(5) 0.6735(2) 0.1742(2) 0.0921(14) Uani 1 1 d . . . . .
H12A H 0.6077 0.6781 0.1227 0.138 Uiso 1 1 calc R U . . .
H12B H 0.6559 0.7135 0.1987 0.138 Uiso 1 1 calc R U . . .
H12C H 0.4984 0.6743 0.1846 0.138 Uiso 1 1 calc R U . . .
C13 C 0.6312(3) 0.28197(17) 0.03999(17) 0.0448(9) Uani 1 1 d . . . . .
H13 H 0.5846 0.2580 -0.0040 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7654(4) 0.23531(18) 0.06850(18) 0.0459(9) Uani 1 1 d . . . . .
C15 C 0.7722(4) 0.1623(2) 0.04875(19) 0.0588(10) Uani 1 1 d . . . . .
H15 H 0.6989 0.1436 0.0143 0.071 Uiso 1 1 calc R U . . .
C16 C 0.8864(5) 0.1168(2) 0.0795(2) 0.0680(11) Uani 1 1 d . . . . .
H16 H 0.8895 0.0680 0.0658 0.082 Uiso 1 1 calc R U . . .
C17 C 0.9945(4) 0.1446(2) 0.1300(2) 0.0641(11) Uani 1 1 d . . . . .
C18 C 1.0956(6) 0.0264(3) 0.1600(3) 0.136(2) Uani 1 1 d . . . . .
H18A H 0.9960 0.0110 0.1700 0.204 Uiso 1 1 calc R U . . .
H18B H 1.1700 0.0041 0.1942 0.204 Uiso 1 1 calc R U . . .
H18C H 1.1134 0.0120 0.1116 0.204 Uiso 1 1 calc R U . . .
C19 C 0.9951(4) 0.2176(2) 0.14694(19) 0.0597(10) Uani 1 1 d . . . . .
H19 H 1.0724 0.2368 0.1790 0.072 Uiso 1 1 calc R U . . .
C20 C 0.8820(4) 0.26242(19) 0.11674(18) 0.0523(9) Uani 1 1 d . . . . .
H20 H 0.8833 0.3117 0.1287 0.063 Uiso 1 1 calc R U . . .
C21 C 0.3568(3) 0.2979(2) 0.04586(17) 0.0460(9) Uani 1 1 d . . . . .
C22 C 0.1478(4) 0.2420(2) -0.03103(19) 0.0743(12) Uani 1 1 d . . . . .
H22A H 0.1251 0.2927 -0.0394 0.112 Uiso 1 1 calc R U . . .
H22B H 0.0623 0.2184 -0.0128 0.112 Uiso 1 1 calc R U . . .
H22C H 0.1691 0.2194 -0.0758 0.112 Uiso 1 1 calc R U . . .
C23 C 0.3225(4) 0.1646(2) 0.0445(2) 0.0587(10) Uani 1 1 d . . . . .
C24 C 0.4647(4) 0.0843(2) 0.1325(2) 0.0859(13) Uani 1 1 d . . . . .
H24A H 0.5718 0.0794 0.1456 0.129 Uiso 1 1 calc R U . . .
H24B H 0.4323 0.0485 0.0965 0.129 Uiso 1 1 calc R U . . .
H24C H 0.4113 0.0772 0.1748 0.129 Uiso 1 1 calc R U . . .
C25 C 0.5067(4) 0.21597(18) 0.1380(2) 0.0479(9) Uani 1 1 d . . . . .
C26 C 0.5024(3) 0.28773(17) 0.09548(17) 0.0419(8) Uani 1 1 d . . . . .
C27 C 0.5346(3) 0.35029(17) 0.15212(16) 0.0431(8) Uani 1 1 d . . . . .
H27 H 0.6321 0.3383 0.1791 0.052 Uiso 1 1 calc R U . . .
C28 C 0.4200(4) 0.35409(17) 0.20856(18) 0.0439(9) Uani 1 1 d . . . . .
C29 C 0.4651(4) 0.34374(19) 0.28223(19) 0.0597(10) Uani 1 1 d . . . . .
H29 H 0.5661 0.3332 0.2970 0.072 Uiso 1 1 calc R U . . .
C30 C 0.3622(4) 0.3490(2) 0.33355(19) 0.0667(11) Uani 1 1 d . . . . .
H30 H 0.3951 0.3418 0.3823 0.080 Uiso 1 1 calc R U . . .
C31 C 0.2122(4) 0.36449(19) 0.3140(2) 0.0536(9) Uani 1 1 d . . . . .
C32 C -0.0357(4) 0.3842(2) 0.3513(2) 0.0866(14) Uani 1 1 d . . . . .
H32A H -0.0459 0.4308 0.3276 0.130 Uiso 1 1 calc R U . . .
H32B H -0.0874 0.3851 0.3947 0.130 Uiso 1 1 calc R U . . .
H32C H -0.0794 0.3470 0.3191 0.130 Uiso 1 1 calc R U . . .
C33 C 0.1662(4) 0.37488(19) 0.2430(2) 0.0582(10) Uani 1 1 d . . . . .
H33 H 0.0651 0.3856 0.2286 0.070 Uiso 1 1 calc R U . . .
C34 C 0.2698(4) 0.36948(19) 0.19145(19) 0.0578(10) Uani 1 1 d . . . . .
H34 H 0.2354 0.3767 0.1428 0.069 Uiso 1 1 calc R U . . .
N1 N 0.7151(3) 0.47705(15) 0.02184(14) 0.0507(8) Uani 1 1 d . . . . .
H1 H 0.7123 0.5218 0.0357 0.061 Uiso 1 1 calc R U . . .
N2 N 0.2806(3) 0.23520(18) 0.02245(15) 0.0532(8) Uani 1 1 d . . . . .
N3 N 0.4322(3) 0.15829(15) 0.10266(17) 0.0573(8) Uani 1 1 d . . . . .
O1 O 0.7288(3) 0.46084(14) 0.22128(14) 0.0762(8) Uani 1 1 d . . . . .
O2 O 0.5975(3) 0.54610(13) 0.15590(12) 0.0589(7) Uani 1 1 d . . . . .
O3 O 1.1066(3) 0.10414(17) 0.16635(17) 0.1004(10) Uani 1 1 d . . . . .
O4 O 0.3135(2) 0.35705(13) 0.02281(12) 0.0565(7) Uani 1 1 d . . . . .
O5 O 0.2627(3) 0.11206(15) 0.01422(15) 0.0824(9) Uani 1 1 d . . . . .
O6 O 0.5795(3) 0.20775(12) 0.19582(14) 0.0617(7) Uani 1 1 d . . . . .
O7 O 0.1201(3) 0.36882(15) 0.36973(14) 0.0841(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(5) . ?
C1 N1 1.385(4) . ?
C1 C6 1.398(4) . ?
C2 C3 1.363(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.437(4) . ?
C7 C8 1.350(4) . ?
C7 C13 1.493(4) . ?
C8 N1 1.378(4) . ?
C8 C9 1.502(4) . ?
C9 C10 1.515(4) . ?
C9 C27 1.547(4) . ?
C9 H9 0.9800 . ?
C10 O1 1.191(4) . ?
C10 O2 1.332(4) . ?
C11 O2 1.456(4) . ?
C11 C12 1.479(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.516(4) . ?
C13 C26 1.608(4) . ?
C13 H13 0.9800 . ?
C14 C15 1.389(4) . ?
C14 C20 1.389(4) . ?
C15 C16 1.389(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(5) . ?
C16 H16 0.9300 . ?
C17 O3 1.363(4) . ?
C17 C19 1.374(5) . ?
C18 O3 1.431(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.371(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O4 1.213(4) . ?
C21 N2 1.380(4) . ?
C21 C26 1.520(4) . ?
C22 N2 1.467(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O5 1.210(4) . ?
C23 N3 1.382(4) . ?
C23 N2 1.395(4) . ?
C24 N3 1.480(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O6 1.203(4) . ?
C25 N3 1.377(4) . ?
C25 C26 1.530(4) . ?
C26 C27 1.560(4) . ?
C27 C28 1.525(4) . ?
C27 H27 0.9800 . ?
C28 C34 1.366(4) . ?
C28 C29 1.395(4) . ?
C29 C30 1.380(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.372(5) . ?
C30 H30 0.9300 . ?
C31 C33 1.351(4) . ?
C31 O7 1.375(4) . ?
C32 O7 1.417(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.387(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 130.8(4) . . ?
C2 C1 C6 121.8(3) . . ?
N1 C1 C6 107.4(3) . . ?
C3 C2 C1 117.7(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.9(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 C7 106.9(3) . . ?
C5 C6 C7 133.8(4) . . ?
C8 C7 C6 107.3(3) . . ?
C8 C7 C13 125.4(3) . . ?
C6 C7 C13 127.2(3) . . ?
C7 C8 N1 109.7(3) . . ?
C7 C8 C9 126.4(3) . . ?
N1 C8 C9 123.9(3) . . ?
C8 C9 C10 108.8(3) . . ?
C8 C9 C27 110.1(3) . . ?
C10 C9 C27 110.8(3) . . ?
C8 C9 H9 109.0 . . ?
C10 C9 H9 109.0 . . ?
C27 C9 H9 109.0 . . ?
O1 C10 O2 124.3(3) . . ?
O1 C10 C9 126.1(3) . . ?
O2 C10 C9 109.5(3) . . ?
O2 C11 C12 107.0(3) . . ?
O2 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O2 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C14 113.1(3) . . ?
C7 C13 C26 109.5(2) . . ?
C14 C13 C26 113.3(2) . . ?
C7 C13 H13 106.8 . . ?
C14 C13 H13 106.8 . . ?
C26 C13 H13 106.8 . . ?
C15 C14 C20 117.7(3) . . ?
C15 C14 C13 120.2(3) . . ?
C20 C14 C13 122.0(3) . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 119.3(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
O3 C17 C16 124.2(4) . . ?
O3 C17 C19 115.5(4) . . ?
C16 C17 C19 120.3(3) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C17 C19 H19 119.9 . . ?
C19 C20 C14 121.1(3) . . ?
C19 C20 H20 119.5 . . ?
C14 C20 H20 119.5 . . ?
O4 C21 N2 120.3(3) . . ?
O4 C21 C26 122.8(3) . . ?
N2 C21 C26 116.6(3) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 N3 122.5(4) . . ?
O5 C23 N2 120.7(4) . . ?
N3 C23 N2 116.9(3) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 N3 121.1(3) . . ?
O6 C25 C26 123.3(3) . . ?
N3 C25 C26 115.4(3) . . ?
C21 C26 C25 113.2(3) . . ?
C21 C26 C27 113.9(3) . . ?
C25 C26 C27 107.0(3) . . ?
C21 C26 C13 103.6(2) . . ?
C25 C26 C13 106.7(2) . . ?
C27 C26 C13 112.4(2) . . ?
C28 C27 C9 110.9(3) . . ?
C28 C27 C26 113.7(2) . . ?
C9 C27 C26 113.9(2) . . ?
C28 C27 H27 105.8 . . ?
C9 C27 H27 105.8 . . ?
C26 C27 H27 105.8 . . ?
C34 C28 C29 115.9(3) . . ?
C34 C28 C27 123.2(3) . . ?
C29 C28 C27 120.9(3) . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 121.3(3) . . ?
C31 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?
C33 C31 C30 118.6(3) . . ?
C33 C31 O7 125.1(3) . . ?
C30 C31 O7 116.3(3) . . ?
O7 C32 H32A 109.5 . . ?
O7 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O7 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 C34 120.0(3) . . ?
C31 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C28 C34 C33 123.3(3) . . ?
C28 C34 H34 118.4 . . ?
C33 C34 H34 118.4 . . ?
C8 N1 C1 108.7(3) . . ?
C8 N1 H1 125.6 . . ?
C1 N1 H1 125.6 . . ?
C21 N2 C23 124.9(3) . . ?
C21 N2 C22 118.4(3) . . ?
C23 N2 C22 116.7(3) . . ?
C25 N3 C23 125.0(3) . . ?
C25 N3 C24 117.3(3) . . ?
C23 N3 C24 117.6(3) . . ?
C10 O2 C11 117.2(3) . . ?
C17 O3 C18 117.4(4) . . ?
C31 O7 C32 117.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.57 3.052(4) 116.6 .
N1 H1 O4 0.86 2.47 3.153(4) 137.0 3_665

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.188
_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_1c
_database_code_depnum_ccdc_archive 'CCDC 2078845'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H33 N3 O6'
_chemical_formula_sum            'C34 H33 N3 O6'
_chemical_formula_weight         579.63

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   11.2751(7)
_cell_length_b                   9.4901(5)
_cell_length_c                   27.4393(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.132(2)
_cell_angle_gamma                90
_cell_volume                     2919.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5940
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      23.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6862
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28987
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.272
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5725
_reflns_number_gt                3030
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+0.8122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5725
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2412(2) 0.6171(3) 0.06940(9) 0.0461(6) Uani 1 1 d . . . . .
C2 C 0.1448(2) 0.5318(3) 0.05388(11) 0.0639(8) Uani 1 1 d . . . . .
H2 H 0.1436 0.4771 0.0257 0.077 Uiso 1 1 calc R U . . .
C3 C 0.0507(3) 0.5317(4) 0.08210(13) 0.0772(9) Uani 1 1 d . . . . .
H3 H -0.0152 0.4750 0.0730 0.093 Uiso 1 1 calc R U . . .
C4 C 0.0523(2) 0.6143(3) 0.12377(12) 0.0713(9) Uani 1 1 d . . . . .
H4 H -0.0133 0.6131 0.1416 0.086 Uiso 1 1 calc R U . . .
C5 C 0.1486(2) 0.6983(3) 0.13943(10) 0.0574(7) Uani 1 1 d . . . . .
H5 H 0.1489 0.7524 0.1677 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2455(2) 0.7004(2) 0.11191(9) 0.0440(6) Uani 1 1 d . . . . .
C7 C 0.3592(2) 0.7705(2) 0.11674(9) 0.0410(6) Uani 1 1 d . . . . .
C8 C 0.4169(2) 0.7287(2) 0.07841(9) 0.0404(6) Uani 1 1 d . . . . .
C9 C 0.53779(19) 0.7739(2) 0.06712(9) 0.0410(6) Uani 1 1 d . . . . .
H9 H 0.5290 0.8330 0.0377 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6066(2) 0.6420(3) 0.05642(11) 0.0451(6) Uani 1 1 d . . . . .
C11 C 0.7023(2) 0.4360(3) 0.08986(11) 0.0643(8) Uani 1 1 d . . . . .
H11A H 0.7660 0.4433 0.0689 0.077 Uiso 1 1 calc R U . . .
H11B H 0.6424 0.3717 0.0747 0.077 Uiso 1 1 calc R U . . .
C12 C 0.7498(3) 0.3836(3) 0.13891(13) 0.0837(10) Uani 1 1 d . . . . .
H12A H 0.8159 0.4411 0.1517 0.125 Uiso 1 1 calc R U . . .
H12B H 0.7760 0.2879 0.1363 0.125 Uiso 1 1 calc R U . . .
H12C H 0.6884 0.3877 0.1605 0.125 Uiso 1 1 calc R U . . .
C13 C 0.4054(2) 0.8743(2) 0.15508(9) 0.0433(6) Uani 1 1 d . . . . .
H13 H 0.3426 0.9452 0.1564 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4261(2) 0.8108(2) 0.20610(9) 0.0451(6) Uani 1 1 d . . . . .
C15 C 0.4966(2) 0.6905(3) 0.21353(11) 0.0599(7) Uani 1 1 d . . . . .
H15 H 0.5252 0.6468 0.1868 0.072 Uiso 1 1 calc R U . . .
C16 C 0.5246(3) 0.6352(3) 0.25982(14) 0.0794(10) Uani 1 1 d . . . . .
H16 H 0.5731 0.5560 0.2645 0.095 Uiso 1 1 calc R U . . .
C17 C 0.4797(4) 0.6987(4) 0.29873(13) 0.0916(12) Uani 1 1 d . . . . .
H17 H 0.5004 0.6642 0.3302 0.110 Uiso 1 1 calc R U . . .
C18 C 0.4050(3) 0.8121(4) 0.29201(11) 0.0810(10) Uani 1 1 d . . . . .
H18 H 0.3724 0.8504 0.3188 0.097 Uiso 1 1 calc R U . . .
C19 C 0.3769(2) 0.8711(3) 0.24590(10) 0.0591(7) Uani 1 1 d . . . . .
C20 C 0.2911(3) 0.9936(3) 0.24128(12) 0.0828(10) Uani 1 1 d . . . . .
H20A H 0.3333 1.0782 0.2348 0.124 Uiso 1 1 calc R U . . .
H20B H 0.2553 1.0043 0.2713 0.124 Uiso 1 1 calc R U . . .
H20C H 0.2300 0.9762 0.2148 0.124 Uiso 1 1 calc R U . . .
C21 C 0.4627(2) 1.0744(3) 0.10643(10) 0.0478(6) Uani 1 1 d . . . . .
C22 C 0.3718(3) 1.3099(3) 0.10355(13) 0.0909(11) Uani 1 1 d . . . . .
H22A H 0.2885 1.2898 0.1040 0.136 Uiso 1 1 calc R U . . .
H22B H 0.3905 1.3128 0.0702 0.136 Uiso 1 1 calc R U . . .
H22C H 0.3901 1.3993 0.1189 0.136 Uiso 1 1 calc R U . . .
C23 C 0.4832(3) 1.2285(3) 0.17871(12) 0.0636(8) Uani 1 1 d . . . . .
C24 C 0.6161(3) 1.1736(3) 0.25194(11) 0.0863(10) Uani 1 1 d . . . . .
H24A H 0.6287 1.0909 0.2720 0.129 Uiso 1 1 calc R U . . .
H24B H 0.5648 1.2376 0.2668 0.129 Uiso 1 1 calc R U . . .
H24C H 0.6913 1.2184 0.2490 0.129 Uiso 1 1 calc R U . . .
C25 C 0.5937(2) 1.0076(3) 0.18378(9) 0.0456(6) Uani 1 1 d . . . . .
C26 C 0.5194(2) 0.9562(2) 0.13764(8) 0.0401(6) Uani 1 1 d . . . . .
C27 C 0.6015(2) 0.8598(2) 0.10977(8) 0.0408(6) Uani 1 1 d . . . . .
H27 H 0.6347 0.7901 0.1338 0.049 Uiso 1 1 calc R U . . .
C28 C 0.7088(2) 0.9369(2) 0.09311(9) 0.0417(6) Uani 1 1 d . . . . .
C29 C 0.8222(2) 0.9059(3) 0.11452(10) 0.0568(7) Uani 1 1 d . . . . .
H29 H 0.8315 0.8416 0.1402 0.068 Uiso 1 1 calc R U . . .
C30 C 0.9223(2) 0.9681(3) 0.09882(11) 0.0658(8) Uani 1 1 d . . . . .
H30 H 0.9976 0.9442 0.1137 0.079 Uiso 1 1 calc R U . . .
C31 C 0.9111(3) 1.0643(3) 0.06165(11) 0.0601(8) Uani 1 1 d . . . . .
C32 C 1.1198(5) 1.0930(7) 0.0596(2) 0.0976(17) Uani 0.651(5) 1 d . . P A 1
H32A H 1.1402 1.1192 0.0932 0.146 Uiso 0.651(5) 1 calc R U P A 1
H32B H 1.1712 1.1414 0.0394 0.146 Uiso 0.651(5) 1 calc R U P A 1
H32C H 1.1294 0.9931 0.0561 0.146 Uiso 0.651(5) 1 calc R U P A 1
C32' C 1.0171(8) 1.2048(14) 0.0125(5) 0.0976(17) Uani 0.349(5) 1 d . . P A 2
H32D H 0.9831 1.1610 -0.0173 0.146 Uiso 0.349(5) 1 calc R U P A 2
H32E H 1.0997 1.2252 0.0103 0.146 Uiso 0.349(5) 1 calc R U P A 2
H32F H 0.9753 1.2909 0.0176 0.146 Uiso 0.349(5) 1 calc R U P A 2
C33 C 0.8002(3) 1.0967(3) 0.03970(11) 0.0623(8) Uani 1 1 d . . . . .
H33 H 0.7918 1.1625 0.0145 0.075 Uiso 1 1 calc R U . . .
C34 C 0.7004(2) 1.0326(3) 0.05461(10) 0.0559(7) Uani 1 1 d . . . . .
H34 H 0.6258 1.0540 0.0385 0.067 Uiso 1 1 calc R U . . .
N1 N 0.34636(17) 0.6371(2) 0.04905(7) 0.0466(5) Uani 1 1 d . . . . .
H1 H 0.3649 0.5989 0.0225 0.056 Uiso 1 1 calc R U . . .
N2 N 0.4429(2) 1.1992(2) 0.13032(8) 0.0576(6) Uani 1 1 d . . . . .
N3 N 0.5602(2) 1.1334(2) 0.20301(8) 0.0545(6) Uani 1 1 d . . . . .
O1 O 0.61403(19) 0.5991(2) 0.01579(7) 0.0753(6) Uani 1 1 d . . . . .
O2 O 0.64990(15) 0.57367(17) 0.09633(7) 0.0567(5) Uani 1 1 d . . . . .
O3 O 0.42762(16) 1.05885(19) 0.06349(7) 0.0626(5) Uani 1 1 d . . . . .
O4 O 0.4546(2) 1.3361(2) 0.19780(9) 0.0986(8) Uani 1 1 d . . . . .
O5 O 0.67500(16) 0.94039(19) 0.20434(6) 0.0593(5) Uani 1 1 d . . . . .
O6 O 1.0087(2) 1.1277(3) 0.04592(11) 0.0985(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.377(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(3) . ?
C7 C8 1.354(3) . ?
C7 C13 1.493(3) . ?
C8 N1 1.378(3) . ?
C8 C9 1.493(3) . ?
C9 C10 1.518(3) . ?
C9 C27 1.540(3) . ?
C9 H9 0.9800 . ?
C10 O1 1.198(3) . ?
C10 O2 1.321(3) . ?
C11 O2 1.452(3) . ?
C11 C12 1.481(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.519(3) . ?
C13 C26 1.618(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.393(3) . ?
C14 C19 1.399(3) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.509(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O3 1.211(3) . ?
C21 N2 1.383(3) . ?
C21 C26 1.511(3) . ?
C22 N2 1.470(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O4 1.207(3) . ?
C23 N3 1.374(3) . ?
C23 N2 1.385(4) . ?
C24 N3 1.471(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.206(3) . ?
C25 N3 1.375(3) . ?
C25 C26 1.522(3) . ?
C26 C27 1.559(3) . ?
C27 C28 1.525(3) . ?
C27 H27 0.9800 . ?
C28 C29 1.380(3) . ?
C28 C34 1.389(3) . ?
C29 C30 1.382(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.364(4) . ?
C30 H30 0.9300 . ?
C31 O6 1.363(3) . ?
C31 C33 1.364(4) . ?
C32 O6 1.311(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32' O6 1.185(13) . ?
C32' H32D 0.9600 . ?
C32' H32E 0.9600 . ?
C32' H32F 0.9600 . ?
C33 C34 1.379(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 H1 0.8600 . ?

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
N1 C1 C2 129.6(2) . . ?
N1 C1 C6 107.7(2) . . ?
C2 C1 C6 122.7(2) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 134.4(2) . . ?
C1 C6 C7 106.7(2) . . ?
C8 C7 C6 106.9(2) . . ?
C8 C7 C13 125.5(2) . . ?
C6 C7 C13 127.6(2) . . ?
C7 C8 N1 110.1(2) . . ?
C7 C8 C9 127.0(2) . . ?
N1 C8 C9 122.9(2) . . ?
C8 C9 C10 107.44(18) . . ?
C8 C9 C27 110.92(19) . . ?
C10 C9 C27 112.14(18) . . ?
C8 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C27 C9 H9 108.8 . . ?
O1 C10 O2 123.3(2) . . ?
O1 C10 C9 123.2(2) . . ?
O2 C10 C9 113.3(2) . . ?
O2 C11 C12 107.7(2) . . ?
O2 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O2 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C14 113.31(19) . . ?
C7 C13 C26 109.65(18) . . ?
C14 C13 C26 114.46(19) . . ?
C7 C13 H13 106.3 . . ?
C14 C13 H13 106.3 . . ?
C26 C13 H13 106.3 . . ?
C15 C14 C19 119.2(2) . . ?
C15 C14 C13 119.3(2) . . ?
C19 C14 C13 121.5(2) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 118.9(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 118.4(3) . . ?
C18 C19 C20 118.0(3) . . ?
C14 C19 C20 123.6(3) . . ?
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 . . ?
O3 C21 N2 120.8(2) . . ?
O3 C21 C26 122.4(2) . . ?
N2 C21 C26 116.6(2) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N3 121.9(3) . . ?
O4 C23 N2 120.7(3) . . ?
N3 C23 N2 117.3(2) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 N3 120.4(2) . . ?
O5 C25 C26 122.9(2) . . ?
N3 C25 C26 116.6(2) . . ?
C21 C26 C25 113.3(2) . . ?
C21 C26 C27 113.27(19) . . ?
C25 C26 C27 107.03(18) . . ?
C21 C26 C13 102.87(18) . . ?
C25 C26 C13 107.01(18) . . ?
C27 C26 C13 113.33(17) . . ?
C28 C27 C9 110.30(18) . . ?
C28 C27 C26 113.42(18) . . ?
C9 C27 C26 115.45(18) . . ?
C28 C27 H27 105.6 . . ?
C9 C27 H27 105.6 . . ?
C26 C27 H27 105.6 . . ?
C29 C28 C34 116.6(2) . . ?
C29 C28 C27 119.9(2) . . ?
C34 C28 C27 123.4(2) . . ?
C28 C29 C30 121.8(3) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
O6 C31 C33 119.6(3) . . ?
O6 C31 C30 121.2(3) . . ?
C33 C31 C30 119.2(3) . . ?
O6 C32 H32A 109.5 . . ?
O6 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O6 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O6 C32' H32D 109.5 . . ?
O6 C32' H32E 109.5 . . ?
H32D C32' H32E 109.5 . . ?
O6 C32' H32F 109.5 . . ?
H32D C32' H32F 109.5 . . ?
H32E C32' H32F 109.5 . . ?
C31 C33 C34 120.6(3) . . ?
C31 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C28 121.5(2) . . ?
C33 C34 H34 119.2 . . ?
C28 C34 H34 119.2 . . ?
C1 N1 C8 108.57(19) . . ?
C1 N1 H1 125.7 . . ?
C8 N1 H1 125.7 . . ?
C21 N2 C23 125.0(2) . . ?
C21 N2 C22 118.8(2) . . ?
C23 N2 C22 116.2(2) . . ?
C23 N3 C25 124.7(2) . . ?
C23 N3 C24 117.4(2) . . ?
C25 N3 C24 117.8(2) . . ?
C10 O2 C11 117.3(2) . . ?
C32' O6 C31 130.7(6) . . ?
C32 O6 C31 125.3(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.18 2.926(3) 145.2 3_665

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044

