# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_exp_8053
_database_code_depnum_ccdc_archive 'CCDC 2235249'
loop_
_audit_author_name
_audit_author_address
'Wenjie Lan'
;China Agricultural University
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_audit_creation_date             2022-06-24
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H14 N2 O2'
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.31
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.5249(9)
_cell_length_b                   11.4884(10)
_cell_length_c                   22.947(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.346(8)
_cell_angle_gamma                90.00
_cell_volume                     3006.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1531
_cell_measurement_temperature    114.85(10)
_cell_measurement_theta_max      25.1650
_cell_measurement_theta_min      3.4860
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6580
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.94
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      114.85(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.6174
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -19.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  -56.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -99.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
  4 omega    4.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   37.0000 -120.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0110305000
_diffrn_orient_matrix_UB_12      0.0009184000
_diffrn_orient_matrix_UB_13      -0.0296303000
_diffrn_orient_matrix_UB_21      0.0097383000
_diffrn_orient_matrix_UB_22      0.0608959000
_diffrn_orient_matrix_UB_23      0.0020559000
_diffrn_orient_matrix_UB_31      0.0604307000
_diffrn_orient_matrix_UB_32      -0.0099227000
_diffrn_orient_matrix_UB_33      0.0097062000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3542
_reflns_number_total             4406
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(15)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0451P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1253
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.02777(18) 0.4225(2) 0.00959(11) 0.0251(6) Uani 1 1 d . . .
N3 N -0.0750(2) 0.4665(3) -0.02171(13) 0.0239(7) Uani 1 1 d . . .
O4 O 0.0098(2) 0.6014(2) -0.07700(12) 0.0313(7) Uani 1 1 d . . .
C20 C -0.2036(3) 0.5772(3) -0.08369(18) 0.0252(8) Uani 1 1 d . . .
H20A H -0.2222 0.5625 -0.1256 0.030 Uiso 1 1 calc R . .
H20B H -0.2250 0.6566 -0.0757 0.030 Uiso 1 1 calc R . .
C31 C 0.1751(3) 0.2762(3) 0.01883(17) 0.0264(9) Uani 1 1 d . . .
C22 C -0.1850(3) 0.4276(3) -0.01301(16) 0.0216(8) Uani 1 1 d . . .
C32 C 0.1619(3) 0.1897(4) 0.05991(18) 0.0345(10) Uani 1 1 d . . .
H32 H 0.0877 0.1606 0.0628 0.041 Uiso 1 1 calc R . .
C19 C -0.0754(3) 0.5552(3) -0.06222(16) 0.0248(9) Uani 1 1 d . . .
C30 C 0.0706(3) 0.3222(3) -0.02131(18) 0.0285(9) Uani 1 1 d . . .
H30A H 0.0929 0.3464 -0.0586 0.034 Uiso 1 1 calc R . .
H30B H 0.0103 0.2629 -0.0287 0.034 Uiso 1 1 calc R . .
C24 C -0.1997(3) 0.3294(3) 0.02618(17) 0.0244(8) Uani 1 1 d . . .
C35 C 0.3826(3) 0.2726(4) 0.0507(2) 0.0417(11) Uani 1 1 d . . .
H35 H 0.4573 0.2997 0.0471 0.050 Uiso 1 1 calc R . .
C29 C -0.1324(3) 0.3182(3) 0.08105(17) 0.0263(9) Uani 1 1 d . . .
H29 H -0.0795 0.3764 0.0950 0.032 Uiso 1 1 calc R . .
C25 C -0.2821(3) 0.2439(3) 0.00607(18) 0.0302(9) Uani 1 1 d . . .
H25 H -0.3291 0.2526 -0.0302 0.036 Uiso 1 1 calc R . .
C21 C -0.2658(3) 0.4913(3) -0.04866(17) 0.0247(9) Uani 1 1 d . . .
C28 C -0.1440(3) 0.2197(4) 0.11541(18) 0.0323(9) Uani 1 1 d . . .
H28 H -0.0982 0.2114 0.1520 0.039 Uiso 1 1 calc R . .
C23 C -0.3888(3) 0.4838(3) -0.05074(18) 0.0289(9) Uani 1 1 d . . .
N4 N -0.4894(3) 0.4793(3) -0.05261(17) 0.0424(9) Uani 1 1 d . . .
C26 C -0.2938(3) 0.1459(4) 0.04022(19) 0.0350(10) Uani 1 1 d . . .
H26 H -0.3479 0.0884 0.0268 0.042 Uiso 1 1 calc R . .
C36 C 0.2867(3) 0.3178(4) 0.01499(18) 0.0329(10) Uani 1 1 d . . .
H36 H 0.2968 0.3764 -0.0118 0.040 Uiso 1 1 calc R . .
C33 C 0.2592(4) 0.1467(4) 0.0968(2) 0.0438(12) Uani 1 1 d . . .
H33 H 0.2497 0.0904 0.1248 0.053 Uiso 1 1 calc R . .
C27 C -0.2243(3) 0.1346(4) 0.0944(2) 0.0354(10) Uani 1 1 d . . .
H27 H -0.2316 0.0686 0.1170 0.043 Uiso 1 1 calc R . .
C34 C 0.3688(4) 0.1877(4) 0.0915(2) 0.0460(12) Uani 1 1 d . . .
H34 H 0.4341 0.1582 0.1156 0.055 Uiso 1 1 calc R . .
O2 O -0.2628(2) 0.1565(2) 0.36594(12) 0.0327(7) Uani 1 1 d . . .
O1 O -0.10791(19) 0.1494(2) 0.28077(11) 0.0270(6) Uani 1 1 d . . .
N1 N -0.1432(2) 0.0552(3) 0.31172(14) 0.0270(8) Uani 1 1 d . . .
C1 C -0.2199(3) 0.0665(3) 0.35207(17) 0.0267(9) Uani 1 1 d . . .
C6 C -0.0238(3) -0.0857(3) 0.26292(17) 0.0241(8) Uani 1 1 d . . .
C13 C 0.0320(3) 0.2976(3) 0.27335(17) 0.0275(9) Uani 1 1 d . . .
C12 C 0.0004(3) 0.2003(3) 0.31148(17) 0.0289(9) Uani 1 1 d . . .
H12A H 0.0624 0.1425 0.3169 0.035 Uiso 1 1 calc R . .
H12B H -0.0117 0.2296 0.3498 0.035 Uiso 1 1 calc R . .
C14 C 0.1108(3) 0.2801(4) 0.23374(18) 0.0318(9) Uani 1 1 d . . .
H14 H 0.1451 0.2074 0.2312 0.038 Uiso 1 1 calc R . .
C2 C -0.2341(3) -0.0562(3) 0.37411(19) 0.0292(9) Uani 1 1 d . . .
H2A H -0.2087 -0.0614 0.4162 0.035 Uiso 1 1 calc R . .
H2B H -0.3150 -0.0816 0.3655 0.035 Uiso 1 1 calc R . .
C4 C -0.1044(3) -0.0592(3) 0.30451(17) 0.0247(9) Uani 1 1 d . . .
C17 C 0.0094(3) 0.4978(4) 0.24049(19) 0.0371(10) Uani 1 1 d . . .
H17 H -0.0250 0.5706 0.2427 0.045 Uiso 1 1 calc R . .
C3 C -0.1563(3) -0.1278(3) 0.34069(18) 0.0266(9) Uani 1 1 d . . .
N2 N -0.1472(3) -0.3516(3) 0.34585(17) 0.0411(9) Uani 1 1 d . . .
C18 C -0.0190(3) 0.4067(4) 0.27580(18) 0.0315(9) Uani 1 1 d . . .
H18 H -0.0732 0.4190 0.3015 0.038 Uiso 1 1 calc R . .
C16 C 0.0892(3) 0.4785(4) 0.20221(19) 0.0377(10) Uani 1 1 d . . .
H16 H 0.1098 0.5394 0.1790 0.045 Uiso 1 1 calc R . .
C15 C 0.1391(3) 0.3704(4) 0.19773(19) 0.0375(11) Uani 1 1 d . . .
H15 H 0.1911 0.3578 0.1709 0.045 Uiso 1 1 calc R . .
C10 C 0.0351(4) -0.0600(4) 0.1669(2) 0.0403(11) Uani 1 1 d . . .
H10 H 0.0229 -0.0257 0.1298 0.048 Uiso 1 1 calc R . .
C11 C -0.0385(3) -0.0354(4) 0.20712(18) 0.0311(9) Uani 1 1 d . . .
H11 H -0.1000 0.0165 0.1969 0.037 Uiso 1 1 calc R . .
C7 C 0.0686(3) -0.1637(3) 0.27724(19) 0.0321(10) Uani 1 1 d . . .
H7 H 0.0805 -0.1990 0.3141 0.038 Uiso 1 1 calc R . .
C5 C -0.1497(3) -0.2508(4) 0.34277(19) 0.0300(9) Uani 1 1 d . . .
C8 C 0.1429(4) -0.1885(4) 0.2361(2) 0.0435(12) Uani 1 1 d . . .
H8 H 0.2038 -0.2415 0.2457 0.052 Uiso 1 1 calc R . .
C9 C 0.1281(4) -0.1364(4) 0.1819(2) 0.0454(12) Uani 1 1 d . . .
H9 H 0.1798 -0.1521 0.1553 0.054 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N3 1.389(4) . ?
O3 C30 1.475(4) . ?
N3 C22 1.385(4) . ?
N3 C19 1.379(5) . ?
O4 C19 1.207(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.509(5) . ?
C20 C21 1.517(5) . ?
C31 C32 1.393(5) . ?
C31 C30 1.502(5) . ?
C31 C36 1.386(5) . ?
C22 C24 1.468(5) . ?
C22 C21 1.360(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.394(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C24 C29 1.386(5) . ?
C24 C25 1.397(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.377(6) . ?
C35 C34 1.379(6) . ?
C29 H29 0.9300 . ?
C29 C28 1.397(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.390(5) . ?
C21 C23 1.414(5) . ?
C28 H28 0.9300 . ?
C28 C27 1.384(6) . ?
C23 N4 1.155(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(6) . ?
C36 H36 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.370(6) . ?
C27 H27 0.9300 . ?
C34 H34 0.9300 . ?
O2 C1 1.209(4) . ?
O1 N1 1.388(4) . ?
O1 C12 1.464(4) . ?
N1 C1 1.376(4) . ?
N1 C4 1.406(4) . ?
C1 C2 1.515(5) . ?
C6 C4 1.458(5) . ?
C6 C11 1.393(5) . ?
C6 C7 1.393(5) . ?
C13 C12 1.497(5) . ?
C13 C14 1.390(5) . ?
C13 C18 1.388(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.393(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.506(5) . ?
C4 C3 1.346(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(6) . ?
C17 C16 1.379(5) . ?
C3 C5 1.416(5) . ?
N2 C5 1.160(5) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.379(6) . ?
C15 H15 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.371(5) . ?
C10 C9 1.389(6) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.393(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.370(6) . ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 O3 C30 110.9(2) . . ?
C22 N3 O3 122.5(3) . . ?
C19 N3 O3 122.5(3) . . ?
C19 N3 C22 115.0(3) . . ?
H20A C20 H20B 109.0 . . ?
C19 C20 H20A 111.1 . . ?
C19 C20 H20B 111.1 . . ?
C19 C20 C21 103.5(3) . . ?
C21 C20 H20A 111.1 . . ?
C21 C20 H20B 111.1 . . ?
C32 C31 C30 120.6(3) . . ?
C36 C31 C32 118.9(3) . . ?
C36 C31 C30 120.5(4) . . ?
N3 C22 C24 121.7(3) . . ?
C21 C22 N3 107.5(3) . . ?
C21 C22 C24 130.6(3) . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.4(4) . . ?
C33 C32 H32 119.8 . . ?
N3 C19 C20 104.5(3) . . ?
O4 C19 N3 126.2(3) . . ?
O4 C19 C20 129.2(4) . . ?
O3 C30 C31 106.0(3) . . ?
O3 C30 H30A 110.5 . . ?
O3 C30 H30B 110.5 . . ?
C31 C30 H30A 110.5 . . ?
C31 C30 H30B 110.5 . . ?
H30A C30 H30B 108.7 . . ?
C29 C24 C22 121.9(3) . . ?
C29 C24 C25 119.9(4) . . ?
C25 C24 C22 118.1(3) . . ?
C36 C35 H35 119.7 . . ?
C36 C35 C34 120.6(4) . . ?
C34 C35 H35 119.7 . . ?
C24 C29 H29 120.0 . . ?
C24 C29 C28 120.1(4) . . ?
C28 C29 H29 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 H25 120.0 . . ?
C22 C21 C20 109.5(3) . . ?
C22 C21 C23 125.7(3) . . ?
C23 C21 C20 124.8(3) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 C29 119.3(4) . . ?
C27 C28 H28 120.4 . . ?
N4 C23 C21 179.0(4) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.5(4) . . ?
C27 C26 H26 120.3 . . ?
C31 C36 H36 119.9 . . ?
C35 C36 C31 120.2(4) . . ?
C35 C36 H36 119.9 . . ?
C32 C33 H33 120.2 . . ?
C34 C33 C32 119.7(4) . . ?
C34 C33 H33 120.2 . . ?
C28 C27 H27 119.4 . . ?
C26 C27 C28 121.2(4) . . ?
C26 C27 H27 119.4 . . ?
C35 C34 H34 119.9 . . ?
C33 C34 C35 120.1(4) . . ?
C33 C34 H34 119.9 . . ?
N1 O1 C12 111.0(3) . . ?
O1 N1 C4 123.2(3) . . ?
C1 N1 O1 122.4(3) . . ?
C1 N1 C4 114.4(3) . . ?
O2 C1 N1 125.8(4) . . ?
O2 C1 C2 129.8(3) . . ?
N1 C1 C2 104.4(3) . . ?
C11 C6 C4 120.7(3) . . ?
C11 C6 C7 118.1(3) . . ?
C7 C6 C4 121.2(4) . . ?
C14 C13 C12 120.8(4) . . ?
C18 C13 C12 120.7(3) . . ?
C18 C13 C14 118.6(4) . . ?
O1 C12 C13 106.2(3) . . ?
O1 C12 H12A 110.5 . . ?
O1 C12 H12B 110.5 . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 C1 103.7(3) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
N1 C4 C6 121.1(3) . . ?
C3 C4 N1 107.3(3) . . ?
C3 C4 C6 131.6(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(4) . . ?
C4 C3 C2 110.2(3) . . ?
C4 C3 C5 125.4(4) . . ?
C5 C3 C2 124.1(3) . . ?
C13 C18 C17 121.2(4) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.1(4) . . ?
C15 C16 H16 119.5 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.3 . . ?
C11 C10 H10 120.2 . . ?
C11 C10 C9 119.6(4) . . ?
C9 C10 H10 120.2 . . ?
C6 C11 H11 119.0 . . ?
C10 C11 C6 121.9(4) . . ?
C10 C11 H11 119.0 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.7(4) . . ?
C8 C7 H7 120.1 . . ?
N2 C5 C3 177.6(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C10 C9 H9 120.3 . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 H9 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 N3 C22 C24 -5.7(5) . . . . ?
O3 N3 C22 C21 177.7(3) . . . . ?
O3 N3 C19 O4 3.0(6) . . . . ?
O3 N3 C19 C20 -178.3(3) . . . . ?
N3 O3 C30 C31 -175.3(3) . . . . ?
N3 C22 C24 C29 43.9(5) . . . . ?
N3 C22 C24 C25 -134.2(4) . . . . ?
N3 C22 C21 C20 0.7(4) . . . . ?
N3 C22 C21 C23 -176.1(3) . . . . ?
C20 C21 C23 N4 -30(25) . . . . ?
C31 C32 C33 C34 -1.6(6) . . . . ?
C22 N3 C19 O4 -179.3(4) . . . . ?
C22 N3 C19 C20 -0.6(4) . . . . ?
C22 C24 C29 C28 -175.9(3) . . . . ?
C22 C24 C25 C26 176.0(3) . . . . ?
C22 C21 C23 N4 146(25) . . . . ?
C32 C31 C30 O3 91.0(4) . . . . ?
C32 C31 C36 C35 1.1(6) . . . . ?
C32 C33 C34 C35 1.1(7) . . . . ?
C19 N3 C22 C24 176.6(3) . . . . ?
C19 N3 C22 C21 0.0(4) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C19 C20 C21 C23 175.8(3) . . . . ?
C30 O3 N3 C22 90.2(4) . . . . ?
C30 O3 N3 C19 -92.2(4) . . . . ?
C30 C31 C32 C33 179.5(4) . . . . ?
C30 C31 C36 C35 -178.0(4) . . . . ?
C24 C22 C21 C20 -175.5(4) . . . . ?
C24 C22 C21 C23 7.7(6) . . . . ?
C24 C29 C28 C27 -0.9(6) . . . . ?
C24 C25 C26 C27 0.7(6) . . . . ?
C29 C24 C25 C26 -2.1(6) . . . . ?
C29 C28 C27 C26 -0.6(6) . . . . ?
C25 C24 C29 C28 2.2(5) . . . . ?
C25 C26 C27 C28 0.6(6) . . . . ?
C21 C20 C19 N3 0.9(4) . . . . ?
C21 C20 C19 O4 179.5(4) . . . . ?
C21 C22 C24 C29 -140.4(4) . . . . ?
C21 C22 C24 C25 41.5(6) . . . . ?
C36 C31 C32 C33 0.5(6) . . . . ?
C36 C31 C30 O3 -90.0(4) . . . . ?
C36 C35 C34 C33 0.4(7) . . . . ?
C34 C35 C36 C31 -1.6(6) . . . . ?
O2 C1 C2 C3 -178.8(4) . . . . ?
O1 N1 C1 O2 -1.4(6) . . . . ?
O1 N1 C1 C2 179.5(3) . . . . ?
O1 N1 C4 C6 -0.4(5) . . . . ?
O1 N1 C4 C3 -179.6(3) . . . . ?
N1 O1 C12 C13 178.1(3) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
N1 C4 C3 C2 0.0(4) . . . . ?
N1 C4 C3 C5 173.5(3) . . . . ?
C1 N1 C4 C6 179.4(3) . . . . ?
C1 N1 C4 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C5 -173.8(4) . . . . ?
C6 C4 C3 C2 -179.1(4) . . . . ?
C6 C4 C3 C5 -5.5(7) . . . . ?
C6 C7 C8 C9 0.9(6) . . . . ?
C13 C14 C15 C16 0.9(6) . . . . ?
C12 O1 N1 C1 92.4(4) . . . . ?
C12 O1 N1 C4 -87.8(4) . . . . ?
C12 C13 C14 C15 179.2(3) . . . . ?
C12 C13 C18 C17 -179.9(4) . . . . ?
C14 C13 C12 O1 -95.4(4) . . . . ?
C14 C13 C18 C17 -1.4(6) . . . . ?
C2 C3 C5 N2 0(12) . . . . ?
C4 N1 C1 O2 178.8(3) . . . . ?
C4 N1 C1 C2 -0.3(4) . . . . ?
C4 C6 C11 C10 -179.1(4) . . . . ?
C4 C6 C7 C8 178.9(4) . . . . ?
C4 C3 C5 N2 -173(11) . . . . ?
C17 C16 C15 C14 -1.9(6) . . . . ?
C18 C13 C12 O1 83.1(4) . . . . ?
C18 C13 C14 C15 0.7(6) . . . . ?
C18 C17 C16 C15 1.2(6) . . . . ?
C16 C17 C18 C13 0.4(6) . . . . ?
C11 C6 C4 N1 -42.6(5) . . . . ?
C11 C6 C4 C3 136.4(4) . . . . ?
C11 C6 C7 C8 0.2(6) . . . . ?
C11 C10 C9 C8 1.7(7) . . . . ?
C7 C6 C4 N1 138.8(4) . . . . ?
C7 C6 C4 C3 -42.3(6) . . . . ?
C7 C6 C11 C10 -0.4(6) . . . . ?
C7 C8 C9 C10 -1.9(7) . . . . ?
C9 C10 C11 C6 -0.6(6) . . . . ?

####################################################################### 
# 
# 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_exp_8572
_database_code_depnum_ccdc_archive 'CCDC 2267290'
loop_
_audit_author_name
_audit_author_address
'Wenjie Lan'
;China Agricultural University
China
;
_audit_update_record             
;
2023-06-03 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_audit_creation_date             2023-06-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C29 H26 N4 O6'
_chemical_formula_sum            'C29 H26 N4 O6'
_chemical_formula_weight         526.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.3944(5)
_cell_length_b                   10.9479(8)
_cell_length_c                   15.5175(9)
_cell_angle_alpha                76.896(6)
_cell_angle_beta                 86.581(5)
_cell_angle_gamma                70.851(6)
_cell_volume                     1311.91(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1281
_cell_measurement_temperature    118.25(10)
_cell_measurement_theta_max      25.3440
_cell_measurement_theta_min      3.7380
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9361
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.92
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      118.25(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8032
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289    0.0000  -90.0000 110

#__ type_ start__ end____ width___ exp.time_
  2 omega   12.00   44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   55.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00    0.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega    8.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   19.0000  150.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0766607000
_diffrn_orient_matrix_UB_12      0.0031316000
_diffrn_orient_matrix_UB_13      -0.0206782000
_diffrn_orient_matrix_UB_21      0.0020712000
_diffrn_orient_matrix_UB_22      -0.0521547000
_diffrn_orient_matrix_UB_23      -0.0205289000
_diffrn_orient_matrix_UB_31      -0.0460602000
_diffrn_orient_matrix_UB_32      0.0470355000
_diffrn_orient_matrix_UB_33      -0.0367985000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3053
_reflns_number_total             5020
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0764
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0689P)²+1.1664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.2052
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5183(3) 0.8280(2) 0.25033(14) 0.0281(6) Uani 1 1 d . . .
O6 O 1.1001(3) 0.6505(2) 0.27487(15) 0.0306(6) Uani 1 1 d . . .
O5 O 0.9660(3) 0.5145(2) 0.35325(18) 0.0392(7) Uani 1 1 d U . .
O2 O 0.5290(3) 1.0101(2) 0.09113(15) 0.0306(6) Uani 1 1 d . . .
N1 N 0.6474(3) 0.9708(3) 0.15850(17) 0.0239(7) Uani 1 1 d . . .
O3 O 0.7856(3) 0.9919(2) 0.43025(16) 0.0391(7) Uani 1 1 d . . .
N2 N 0.4202(3) 0.6771(3) 0.33570(19) 0.0315(7) Uani 1 1 d . . .
H2A H 0.4174 0.6160 0.3831 0.038 Uiso 1 1 calc R . .
H2B H 0.3485 0.6967 0.2916 0.038 Uiso 1 1 calc R . .
O4 O 0.6872(4) 0.8535(3) 0.52855(18) 0.0548(9) Uani 1 1 d . . .
N3 N 0.6562(4) 0.5392(3) 0.53203(19) 0.0348(8) Uani 1 1 d . . .
C3 C 0.6521(4) 0.7217(3) 0.3930(2) 0.0264(8) Uani 1 1 d . . .
C1 C 0.6550(4) 0.6223(4) 0.4709(2) 0.0278(8) Uani 1 1 d . . .
N4 N 1.1296(4) 0.9816(3) 0.2934(2) 0.0400(8) Uani 1 1 d . . .
C25 C 1.0177(4) 0.6205(3) 0.3365(2) 0.0299(8) Uani 1 1 d U . .
C10 C 0.8210(4) 1.1135(3) 0.0864(2) 0.0253(8) Uani 1 1 d . . .
C2 C 0.5328(4) 0.7401(3) 0.3308(2) 0.0250(8) Uani 1 1 d . . .
C8 C 0.8537(4) 0.9619(3) 0.2438(2) 0.0250(8) Uani 1 1 d . . .
C6 C 0.6405(4) 0.8871(3) 0.2377(2) 0.0239(8) Uani 1 1 d . . .
C7 C 0.7776(4) 1.0209(3) 0.1605(2) 0.0236(8) Uani 1 1 d . . .
C9 C 1.0049(4) 0.9749(3) 0.2708(2) 0.0281(8) Uani 1 1 d . . .
C5 C 0.7640(4) 0.8781(3) 0.2931(2) 0.0255(8) Uani 1 1 d . . .
C23 C 0.7462(5) 0.8821(4) 0.4588(2) 0.0331(9) Uani 1 1 d . . .
C4 C 0.7812(5) 0.7944(4) 0.3856(2) 0.0345(9) Uani 1 1 d . . .
C15 C 0.7982(5) 1.1093(4) -0.0014(2) 0.0330(9) Uani 1 1 d . . .
H15 H 0.7501 1.0476 -0.0137 0.040 Uiso 1 1 calc R . .
C24 C 0.9624(5) 0.7007(4) 0.4079(2) 0.0377(9) Uani 1 1 d U . .
H24A H 1.0387 0.7525 0.4097 0.045 Uiso 1 1 calc R . .
H24B H 0.9664 0.6406 0.4666 0.045 Uiso 1 1 calc R . .
C11 C 0.8900(5) 1.2059(3) 0.1027(2) 0.0322(9) Uani 1 1 d . . .
H11 H 0.9044 1.2109 0.1619 0.039 Uiso 1 1 calc R . .
C16 C 0.3681(4) 1.1035(4) 0.1145(3) 0.0361(9) Uani 1 1 d . . .
H16A H 0.2925 1.1403 0.0618 0.043 Uiso 1 1 calc R . .
H16B H 0.3124 1.0540 0.1609 0.043 Uiso 1 1 calc R . .
C17 C 0.3903(4) 1.2146(4) 0.1468(2) 0.0334(9) Uani 1 1 d . . .
C26 C 0.7455(5) 1.0876(4) 0.4852(3) 0.0413(10) Uani 1 1 d . . .
H26A H 0.8089 1.0488 0.5421 0.050 Uiso 1 1 calc R . .
H26B H 0.6234 1.1155 0.4978 0.050 Uiso 1 1 calc R . .
C14 C 0.8455(5) 1.1952(4) -0.0705(2) 0.0403(10) Uani 1 1 d . . .
H14 H 0.8298 1.1919 -0.1300 0.048 Uiso 1 1 calc R . .
C12 C 0.9376(5) 1.2903(4) 0.0336(3) 0.0441(11) Uani 1 1 d . . .
H12 H 0.9859 1.3521 0.0456 0.053 Uiso 1 1 calc R . .
C27 C 0.7946(5) 1.2048(4) 0.4351(3) 0.0462(11) Uani 1 1 d . . .
H27A H 0.7383 1.2377 0.3769 0.069 Uiso 1 1 calc R . .
H27B H 0.9171 1.1776 0.4275 0.069 Uiso 1 1 calc R . .
H27C H 0.7604 1.2752 0.4683 0.069 Uiso 1 1 calc R . .
C18 C 0.4078(5) 1.3247(4) 0.0883(3) 0.0491(11) Uani 1 1 d . . .
H18 H 0.4015 1.3326 0.0262 0.059 Uiso 1 1 calc R . .
C13 C 0.9154(5) 1.2855(4) -0.0534(3) 0.0445(11) Uani 1 1 d . . .
H13 H 0.9479 1.3439 -0.1008 0.053 Uiso 1 1 calc R . .
C28 C 0.9880(6) 0.4443(5) 0.2804(4) 0.0683(15) Uani 1 1 d U . .
H28A H 1.0056 0.3489 0.3043 0.082 Uiso 1 1 calc R . .
H28B H 1.0873 0.4531 0.2450 0.082 Uiso 1 1 calc R . .
C22 C 0.3964(5) 1.2034(5) 0.2380(3) 0.0495(12) Uani 1 1 d . . .
H22 H 0.3838 1.1270 0.2772 0.059 Uiso 1 1 calc R . .
C20 C 0.4434(6) 1.4078(6) 0.2157(5) 0.0720(17) Uani 1 1 d . . .
H20 H 0.4657 1.4728 0.2400 0.086 Uiso 1 1 calc R . .
C19 C 0.4356(6) 1.4264(5) 0.1229(5) 0.0717(17) Uani 1 1 d . . .
H19 H 0.4483 1.5038 0.0849 0.086 Uiso 1 1 calc R . .
C21 C 0.4203(6) 1.3009(6) 0.2711(4) 0.0690(15) Uani 1 1 d . . .
H21 H 0.4206 1.2938 0.3332 0.083 Uiso 1 1 calc R . .
C29 C 0.8289(7) 0.5066(7) 0.2230(4) 0.096(2) Uani 1 1 d . . .
H29A H 0.8382 0.4604 0.1748 0.143 Uiso 1 1 calc R . .
H29B H 0.8147 0.6003 0.1982 0.143 Uiso 1 1 calc R . .
H29C H 0.7311 0.4994 0.2590 0.143 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.376(4) . ?
O1 C6 1.366(4) . ?
O6 C25 1.195(4) . ?
O5 C25 1.336(4) . ?
O5 C28 1.476(5) . ?
O2 N1 1.380(3) . ?
O2 C16 1.485(4) . ?
N1 C6 1.367(4) . ?
N1 C7 1.378(4) . ?
O3 C23 1.324(4) . ?
O3 C26 1.442(4) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C2 1.331(4) . ?
O4 C23 1.183(4) . ?
N3 C1 1.154(4) . ?
C3 C1 1.426(4) . ?
C3 C2 1.368(4) . ?
C3 C4 1.526(5) . ?
N4 C9 1.154(4) . ?
C25 C24 1.525(5) . ?
C10 C7 1.466(4) . ?
C10 C15 1.401(5) . ?
C10 C11 1.392(5) . ?
C8 C7 1.394(4) . ?
C8 C9 1.420(5) . ?
C8 C5 1.436(4) . ?
C6 C5 1.351(4) . ?
C5 C4 1.503(4) . ?
C23 C4 1.603(5) . ?
C4 C24 1.538(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.389(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.380(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.484(5) . ?
C17 C18 1.379(5) . ?
C17 C22 1.394(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.509(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.382(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.429(7) . ?
C13 H13 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.520(7) . ?
C22 H22 0.9500 . ?
C22 C21 1.358(7) . ?
C20 H20 0.9500 . ?
C20 C19 1.410(8) . ?
C20 C21 1.349(8) . ?
C19 H19 0.9500 . ?
C21 H21 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C2 113.1(2) . . ?
C25 O5 C28 115.3(3) . . ?
N1 O2 C16 111.0(2) . . ?
C6 N1 O2 124.3(3) . . ?
C6 N1 C7 109.8(3) . . ?
C7 N1 O2 125.5(2) . . ?
C23 O3 C26 118.3(3) . . ?
H2A N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
C1 C3 C4 118.4(3) . . ?
C2 C3 C1 115.2(3) . . ?
C2 C3 C4 126.3(3) . . ?
N3 C1 C3 177.6(4) . . ?
O6 C25 O5 125.8(4) . . ?
O6 C25 C24 122.5(3) . . ?
O5 C25 C24 111.7(3) . . ?
C15 C10 C7 121.2(3) . . ?
C11 C10 C7 120.0(3) . . ?
C11 C10 C15 118.8(3) . . ?
N2 C2 O1 110.2(3) . . ?
N2 C2 C3 127.3(3) . . ?
C3 C2 O1 122.5(3) . . ?
C7 C8 C9 124.3(3) . . ?
C7 C8 C5 109.2(3) . . ?
C9 C8 C5 126.3(3) . . ?
O1 C6 N1 119.4(3) . . ?
C5 C6 O1 130.1(3) . . ?
C5 C6 N1 110.5(3) . . ?
N1 C7 C10 124.3(3) . . ?
N1 C7 C8 105.4(3) . . ?
C8 C7 C10 130.3(3) . . ?
N4 C9 C8 178.1(4) . . ?
C8 C5 C4 134.0(3) . . ?
C6 C5 C8 105.1(3) . . ?
C6 C5 C4 120.9(3) . . ?
O3 C23 C4 111.7(3) . . ?
O4 C23 O3 124.5(4) . . ?
O4 C23 C4 123.7(3) . . ?
C3 C4 C23 109.9(3) . . ?
C3 C4 C24 113.2(3) . . ?
C5 C4 C3 106.5(3) . . ?
C5 C4 C23 112.0(3) . . ?
C5 C4 C24 112.3(3) . . ?
C24 C4 C23 102.9(3) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.1(4) . . ?
C14 C15 H15 119.9 . . ?
C25 C24 C4 108.0(3) . . ?
C25 C24 H24A 110.1 . . ?
C25 C24 H24B 110.1 . . ?
C4 C24 H24A 110.1 . . ?
C4 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
O2 C16 H16A 108.9 . . ?
O2 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 O2 113.4(3) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 C22 120.9(4) . . ?
C22 C17 C16 118.2(4) . . ?
O3 C26 H26A 110.3 . . ?
O3 C26 H26B 110.3 . . ?
O3 C26 C27 107.2(3) . . ?
H26A C26 H26B 108.5 . . ?
C27 C26 H26A 110.3 . . ?
C27 C26 H26B 110.3 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(5) . . ?
C19 C18 H18 120.7 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
O5 C28 H28A 110.2 . . ?
O5 C28 H28B 110.2 . . ?
O5 C28 C29 107.5(4) . . ?
H28A C28 H28B 108.5 . . ?
C29 C28 H28A 110.2 . . ?
C29 C28 H28B 110.2 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.6(5) . . ?
C21 C22 H22 119.7 . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C21 C20 C19 122.3(5) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 C18 117.5(5) . . ?
C20 C19 H19 121.2 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0(5) . . ?
C20 C21 H21 120.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C5 C8 180.0(4) . . . . ?
O1 C6 C5 C4 -1.1(6) . . . . ?
O6 C25 C24 C4 97.2(4) . . . . ?
O5 C25 C24 C4 -84.2(3) . . . . ?
O2 N1 C6 O1 5.9(5) . . . . ?
O2 N1 C6 C5 -173.7(3) . . . . ?
O2 N1 C7 C10 -7.1(5) . . . . ?
O2 N1 C7 C8 174.4(3) . . . . ?
O2 C16 C17 C18 81.7(4) . . . . ?
O2 C16 C17 C22 -97.1(4) . . . . ?
N1 O2 C16 C17 49.9(4) . . . . ?
N1 C6 C5 C8 -0.4(4) . . . . ?
N1 C6 C5 C4 178.5(3) . . . . ?
O3 C23 C4 C3 -147.2(3) . . . . ?
O3 C23 C4 C5 -28.9(4) . . . . ?
O3 C23 C4 C24 92.0(3) . . . . ?
O4 C23 C4 C3 30.6(5) . . . . ?
O4 C23 C4 C5 148.8(4) . . . . ?
O4 C23 C4 C24 -90.3(4) . . . . ?
C3 C4 C24 C25 67.0(4) . . . . ?
C1 C3 C2 O1 -177.0(3) . . . . ?
C1 C3 C2 N2 0.8(6) . . . . ?
C1 C3 C4 C5 172.4(3) . . . . ?
C1 C3 C4 C23 -66.1(4) . . . . ?
C1 C3 C4 C24 48.4(5) . . . . ?
C25 O5 C28 C29 -89.5(4) . . . . ?
C10 C15 C14 C13 -0.1(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C2 O1 C6 N1 176.1(3) . . . . ?
C2 O1 C6 C5 -4.3(5) . . . . ?
C2 C3 C1 N3 38(9) . . . . ?
C2 C3 C4 C5 -6.2(5) . . . . ?
C2 C3 C4 C23 115.4(4) . . . . ?
C2 C3 C4 C24 -130.2(4) . . . . ?
C8 C5 C4 C3 -175.7(4) . . . . ?
C8 C5 C4 C23 64.1(5) . . . . ?
C8 C5 C4 C24 -51.2(6) . . . . ?
C6 O1 C2 N2 -174.3(3) . . . . ?
C6 O1 C2 C3 3.9(5) . . . . ?
C6 N1 C7 C10 179.9(3) . . . . ?
C6 N1 C7 C8 1.4(4) . . . . ?
C6 C5 C4 C3 5.7(5) . . . . ?
C6 C5 C4 C23 -114.5(4) . . . . ?
C6 C5 C4 C24 130.2(4) . . . . ?
C7 N1 C6 O1 179.0(3) . . . . ?
C7 N1 C6 C5 -0.6(4) . . . . ?
C7 C10 C15 C14 -177.8(3) . . . . ?
C7 C10 C11 C12 177.5(3) . . . . ?
C7 C8 C9 N4 -127(11) . . . . ?
C7 C8 C5 C6 1.3(4) . . . . ?
C7 C8 C5 C4 -177.4(4) . . . . ?
C9 C8 C7 N1 173.1(3) . . . . ?
C9 C8 C7 C10 -5.2(6) . . . . ?
C9 C8 C5 C6 -173.3(4) . . . . ?
C9 C8 C5 C4 7.9(7) . . . . ?
C5 C8 C7 N1 -1.7(4) . . . . ?
C5 C8 C7 C10 -180.0(3) . . . . ?
C5 C8 C9 N4 47(11) . . . . ?
C5 C4 C24 C25 -53.6(4) . . . . ?
C23 O3 C26 C27 -176.9(3) . . . . ?
C23 C4 C24 C25 -174.3(3) . . . . ?
C4 C3 C1 N3 -140(9) . . . . ?
C4 C3 C2 O1 1.6(6) . . . . ?
C4 C3 C2 N2 179.4(4) . . . . ?
C15 C10 C7 N1 -32.5(5) . . . . ?
C15 C10 C7 C8 145.4(4) . . . . ?
C15 C10 C11 C12 -1.1(5) . . . . ?
C15 C14 C13 C12 -0.2(6) . . . . ?
C11 C10 C7 N1 149.0(3) . . . . ?
C11 C10 C7 C8 -33.0(5) . . . . ?
C11 C10 C15 C14 0.7(5) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C16 O2 N1 C6 71.6(4) . . . . ?
C16 O2 N1 C7 -100.4(4) . . . . ?
C16 C17 C18 C19 -177.6(3) . . . . ?
C16 C17 C22 C21 178.6(4) . . . . ?
C17 C18 C19 C20 0.0(6) . . . . ?
C17 C22 C21 C20 -2.0(7) . . . . ?
C26 O3 C23 O4 -3.8(6) . . . . ?
C26 O3 C23 C4 173.9(3) . . . . ?
C18 C17 C22 C21 -0.2(6) . . . . ?
C28 O5 C25 O6 -11.6(5) . . . . ?
C28 O5 C25 C24 169.8(3) . . . . ?
C22 C17 C18 C19 1.2(6) . . . . ?
C19 C20 C21 C22 3.2(8) . . . . ?
C21 C20 C19 C18 -2.2(7) . . . . ?

