# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_6359
_database_code_depnum_ccdc_archive 'CCDC 2064724'
loop_
_audit_author_name
_audit_author_address
FRA
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2021-02-23 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_audit_creation_date             2020-08-31
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H17 N O2'
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9864(4)
_cell_length_b                   15.1402(11)
_cell_length_c                   24.1044(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.057(4)
_cell_angle_gamma                90.00
_cell_volume                     3266.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4628
_cell_measurement_temperature    109(3)
_cell_measurement_theta_max      28.2550
_cell_measurement_theta_min      3.6640
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91247
_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    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19832
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.18
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.8533
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -19.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
  4 omega  -14.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210   57.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -57.00  -32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -37.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -84.00  -53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -19.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -77.0000  150.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0719098000
_diffrn_orient_matrix_UB_12      0.0132756000
_diffrn_orient_matrix_UB_13      -0.0067220000
_diffrn_orient_matrix_UB_21      0.0267617000
_diffrn_orient_matrix_UB_22      -0.0435997000
_diffrn_orient_matrix_UB_23      0.0049788000
_diffrn_orient_matrix_UB_31      -0.0196563000
_diffrn_orient_matrix_UB_32      -0.0107727000
_diffrn_orient_matrix_UB_33      -0.0283294000
_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                5046
_reflns_number_total             6401
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.212
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0321P)²+1.1321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1014
_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 0.10944(13) 0.92135(8) 0.21348(5) 0.0230(3) Uani 1 1 d . . .
N1 N 0.00151(15) 1.01623(9) 0.27219(5) 0.0181(3) Uani 1 1 d . . .
O2 O -0.23507(14) 1.49694(8) 0.32964(5) 0.0272(3) Uani 1 1 d . . .
C8 C -0.00296(18) 1.17423(11) 0.25576(7) 0.0179(4) Uani 1 1 d . . .
C9 C -0.03144(18) 1.10286(11) 0.28638(7) 0.0187(4) Uani 1 1 d . . .
H9 H -0.0762 1.1120 0.3193 0.022 Uiso 1 1 calc R . .
C2 C 0.10885(18) 1.07417(11) 0.19096(6) 0.0174(4) Uani 1 1 d . . .
C3 C 0.18005(18) 1.05791(11) 0.14236(7) 0.0203(4) Uani 1 1 d . . .
H3 H 0.2051 1.0004 0.1333 0.024 Uiso 1 1 calc R . .
C1 C 0.07606(18) 0.99723(11) 0.22534(7) 0.0181(4) Uani 1 1 d . . .
C10 C -0.05474(18) 1.26192(11) 0.27488(6) 0.0174(4) Uani 1 1 d . . .
C7 C 0.06970(18) 1.16071(11) 0.20502(7) 0.0185(4) Uani 1 1 d . . .
C21 C -0.20738(19) 0.95440(12) 0.31685(7) 0.0216(4) Uani 1 1 d . . .
H21 H -0.2632 1.0037 0.3050 0.026 Uiso 1 1 calc R . .
C16 C -0.05981(19) 0.94642(11) 0.30388(6) 0.0180(4) Uani 1 1 d . . .
C5 C 0.17336(19) 1.21306(12) 0.12136(7) 0.0224(4) Uani 1 1 d . . .
H5 H 0.1949 1.2595 0.0981 0.027 Uiso 1 1 calc R . .
C11 C 0.03637(19) 1.33601(11) 0.28227(7) 0.0197(4) Uani 1 1 d . . .
H11 H 0.1356 1.3323 0.2743 0.024 Uiso 1 1 calc R . .
C13 C -0.16605(19) 1.42137(11) 0.31308(6) 0.0191(4) Uani 1 1 d . . .
C12 C -0.01775(19) 1.41562(11) 0.30137(7) 0.0200(4) Uani 1 1 d . . .
H12 H 0.0448 1.4645 0.3062 0.024 Uiso 1 1 calc R . .
C4 C 0.2130(2) 1.12658(12) 0.10797(7) 0.0231(4) Uani 1 1 d . . .
H4 H 0.2613 1.1156 0.0761 0.028 Uiso 1 1 calc R . .
C17 C 0.02341(19) 0.87272(11) 0.32104(7) 0.0205(4) Uani 1 1 d . . .
H17 H 0.1223 0.8675 0.3129 0.025 Uiso 1 1 calc R . .
C14 C -0.25814(19) 1.34806(11) 0.30689(7) 0.0196(4) Uani 1 1 d . . .
H14 H -0.3566 1.3515 0.3158 0.024 Uiso 1 1 calc R . .
C15 C -0.20334(19) 1.26988(11) 0.28752(6) 0.0185(4) Uani 1 1 d . . .
H15 H -0.2665 1.2213 0.2827 0.022 Uiso 1 1 calc R . .
C20 C -0.2710(2) 0.88902(12) 0.34731(7) 0.0240(4) Uani 1 1 d . . .
H20 H -0.3687 0.8950 0.3566 0.029 Uiso 1 1 calc R . .
C6 C 0.10277(18) 1.22962(11) 0.16866(7) 0.0203(4) Uani 1 1 d . . .
H6 H 0.0764 1.2873 0.1768 0.024 Uiso 1 1 calc R . .
C18 C -0.0426(2) 0.80695(12) 0.35051(7) 0.0242(4) Uani 1 1 d . . .
H18 H 0.0121 0.7568 0.3615 0.029 Uiso 1 1 calc R . .
C19 C -0.1890(2) 0.81482(12) 0.36387(7) 0.0249(4) Uani 1 1 d . . .
H19 H -0.2319 0.7704 0.3839 0.030 Uiso 1 1 calc R . .
C22 C -0.1488(3) 1.57382(13) 0.34042(9) 0.0420(6) Uani 1 1 d . . .
H22A H -0.1145 1.5952 0.3063 0.063 Uiso 1 1 calc R . .
H22B H -0.0644 1.5603 0.3663 0.063 Uiso 1 1 calc R . .
H22C H -0.2087 1.6183 0.3560 0.063 Uiso 1 1 calc R . .
O3 O 0.15573(14) 0.42238(8) 0.10730(5) 0.0243(3) Uani 1 1 d . . .
N2 N 0.22658(16) 0.52020(9) 0.04218(5) 0.0190(3) Uani 1 1 d . . .
C23 C 0.18010(18) 0.49935(11) 0.09424(7) 0.0182(4) Uani 1 1 d . . .
C25 C 0.12188(18) 0.55764(12) 0.18474(7) 0.0210(4) Uani 1 1 d . . .
H25 H 0.1139 0.4996 0.1968 0.025 Uiso 1 1 calc R . .
C29 C 0.17301(18) 0.66252(11) 0.11197(7) 0.0179(4) Uani 1 1 d . . .
C31 C 0.23963(19) 0.60683(11) 0.02419(7) 0.0199(4) Uani 1 1 d . . .
H31 H 0.2674 0.6164 -0.0116 0.024 Uiso 1 1 calc R . .
C43 C 0.18145(19) 0.44384(12) -0.04722(7) 0.0225(4) Uani 1 1 d . . .
H43 H 0.1107 0.4863 -0.0588 0.027 Uiso 1 1 calc R . .
C24 C 0.15997(18) 0.57505(11) 0.13066(6) 0.0178(4) Uani 1 1 d . . .
C27 C 0.10355(19) 0.71353(12) 0.20138(7) 0.0215(4) Uani 1 1 d . . .
H27 H 0.0829 0.7597 0.2250 0.026 Uiso 1 1 calc R . .
C30 C 0.21410(18) 0.67765(11) 0.05586(7) 0.0188(4) Uani 1 1 d . . .
O4 O 0.27324(16) 1.02710(8) -0.02288(5) 0.0367(3) Uani 1 1 d . . .
C28 C 0.14107(18) 0.73155(11) 0.14844(7) 0.0198(4) Uani 1 1 d . . .
H28 H 0.1454 0.7899 0.1365 0.024 Uiso 1 1 calc R . .
C38 C 0.25748(19) 0.44882(11) 0.00518(7) 0.0194(4) Uani 1 1 d . . .
C33 C 0.3355(2) 0.82770(12) 0.05855(7) 0.0238(4) Uani 1 1 d . . .
H33 H 0.3974 0.8096 0.0894 0.029 Uiso 1 1 calc R . .
C26 C 0.09626(19) 0.62648(12) 0.21992(7) 0.0218(4) Uani 1 1 d . . .
H26 H 0.0740 0.6149 0.2562 0.026 Uiso 1 1 calc R . .
C37 C 0.1403(2) 0.79781(11) -0.01269(7) 0.0223(4) Uani 1 1 d . . .
H37 H 0.0707 0.7594 -0.0304 0.027 Uiso 1 1 calc R . .
C32 C 0.22969(19) 0.76870(11) 0.03362(7) 0.0197(4) Uani 1 1 d . . .
C39 C 0.3637(2) 0.38626(12) 0.02252(7) 0.0247(4) Uani 1 1 d . . .
H39 H 0.4157 0.3907 0.0575 0.030 Uiso 1 1 calc R . .
C42 C 0.2123(2) 0.37443(12) -0.08225(7) 0.0249(4) Uani 1 1 d . . .
H42 H 0.1622 0.3708 -0.1176 0.030 Uiso 1 1 calc R . .
C35 C 0.2552(2) 0.94099(12) -0.00722(7) 0.0264(4) Uani 1 1 d . . .
C34 C 0.3494(2) 0.91221(12) 0.03813(7) 0.0269(4) Uani 1 1 d . . .
H34 H 0.4218 0.9500 0.0547 0.032 Uiso 1 1 calc R . .
C41 C 0.3163(2) 0.31109(12) -0.06504(7) 0.0264(4) Uani 1 1 d . . .
H41 H 0.3356 0.2645 -0.0885 0.032 Uiso 1 1 calc R . .
C36 C 0.1526(2) 0.88326(12) -0.03316(7) 0.0252(4) Uani 1 1 d . . .
H36 H 0.0918 0.9014 -0.0643 0.030 Uiso 1 1 calc R . .
C40 C 0.3922(2) 0.31713(12) -0.01236(7) 0.0277(4) Uani 1 1 d . . .
H40 H 0.4625 0.2745 -0.0006 0.033 Uiso 1 1 calc R . .
C44 C 0.1500(3) 1.06758(13) -0.05497(9) 0.0404(5) Uani 1 1 d . . .
H44A H 0.1392 1.0420 -0.0915 0.061 Uiso 1 1 calc R . .
H44B H 0.1679 1.1299 -0.0579 0.061 Uiso 1 1 calc R . .
H44C H 0.0602 1.0581 -0.0370 0.061 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 C1 1.2274(19) . ?
N1 C9 1.394(2) . ?
N1 C1 1.393(2) . ?
N1 C16 1.442(2) . ?
O2 C13 1.377(2) . ?
O2 C22 1.410(2) . ?
C8 C9 1.346(2) . ?
C8 C10 1.493(2) . ?
C8 C7 1.451(2) . ?
C9 H9 0.9300 . ?
C2 C3 1.405(2) . ?
C2 C1 1.474(2) . ?
C2 C7 1.406(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.401(2) . ?
C7 C6 1.411(2) . ?
C21 H21 0.9300 . ?
C21 C16 1.394(2) . ?
C21 C20 1.385(2) . ?
C16 C17 1.386(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.402(2) . ?
C5 C6 1.376(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(2) . ?
C13 C12 1.389(2) . ?
C13 C14 1.385(2) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(2) . ?
C15 H15 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.383(3) . ?
C6 H6 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O3 C23 1.2317(19) . ?
N2 C23 1.393(2) . ?
N2 C31 1.390(2) . ?
N2 C38 1.444(2) . ?
C23 C24 1.464(2) . ?
C25 H25 0.9300 . ?
C25 C24 1.402(2) . ?
C25 C26 1.376(2) . ?
C29 C24 1.407(2) . ?
C29 C30 1.451(2) . ?
C29 C28 1.411(2) . ?
C31 H31 0.9300 . ?
C31 C30 1.348(2) . ?
C43 H43 0.9300 . ?
C43 C38 1.384(2) . ?
C43 C42 1.391(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.376(2) . ?
C27 C26 1.395(2) . ?
C30 C32 1.490(2) . ?
O4 C35 1.371(2) . ?
O4 C44 1.432(2) . ?
C28 H28 0.9300 . ?
C38 C39 1.383(2) . ?
C33 H33 0.9300 . ?
C33 C32 1.401(2) . ?
C33 C34 1.381(2) . ?
C26 H26 0.9300 . ?
C37 H37 0.9300 . ?
C37 C32 1.388(2) . ?
C37 C36 1.393(2) . ?
C39 H39 0.9300 . ?
C39 C40 1.381(2) . ?
C42 H42 0.9300 . ?
C42 C41 1.377(3) . ?
C35 C34 1.392(3) . ?
C35 C36 1.380(3) . ?
C34 H34 0.9300 . ?
C41 H41 0.9300 . ?
C41 C40 1.391(3) . ?
C36 H36 0.9300 . ?
C40 H40 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C16 117.42(13) . . ?
C1 N1 C9 121.40(14) . . ?
C1 N1 C16 120.78(13) . . ?
C13 O2 C22 119.00(14) . . ?
C9 C8 C10 117.72(15) . . ?
C9 C8 C7 118.08(15) . . ?
C7 C8 C10 124.14(15) . . ?
N1 C9 H9 117.8 . . ?
C8 C9 N1 124.48(15) . . ?
C8 C9 H9 117.8 . . ?
C3 C2 C1 117.29(15) . . ?
C3 C2 C7 120.42(15) . . ?
C7 C2 C1 122.29(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.47(16) . . ?
C4 C3 H3 119.8 . . ?
O1 C1 N1 121.80(15) . . ?
O1 C1 C2 122.93(15) . . ?
N1 C1 C2 115.27(14) . . ?
C11 C10 C8 124.11(15) . . ?
C11 C10 C15 117.67(15) . . ?
C15 C10 C8 118.20(15) . . ?
C2 C7 C8 118.39(15) . . ?
C2 C7 C6 117.94(15) . . ?
C6 C7 C8 123.67(16) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C16 120.12(17) . . ?
C21 C16 N1 118.08(15) . . ?
C17 C16 N1 121.80(15) . . ?
C17 C16 C21 120.12(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.40(16) . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.43(16) . . ?
C12 C11 H11 119.3 . . ?
O2 C13 C12 125.14(16) . . ?
O2 C13 C14 114.64(15) . . ?
C14 C13 C12 120.20(16) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.37(16) . . ?
C13 C12 H12 120.3 . . ?
C3 C4 C5 119.58(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.14(16) . . ?
C18 C17 H17 120.4 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.77(16) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.54(16) . . ?
C14 C15 H15 119.2 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 119.97(17) . . ?
C19 C20 H20 120.0 . . ?
C7 C6 H6 119.4 . . ?
C5 C6 C7 121.18(16) . . ?
C5 C6 H6 119.4 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.99(17) . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 119.65(17) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 N2 C38 118.44(13) . . ?
C31 N2 C23 122.35(14) . . ?
C31 N2 C38 119.19(13) . . ?
O3 C23 N2 121.24(15) . . ?
O3 C23 C24 123.58(15) . . ?
N2 C23 C24 115.16(14) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 119.91(16) . . ?
C24 C29 C30 118.82(15) . . ?
C24 C29 C28 118.07(15) . . ?
C28 C29 C30 123.08(15) . . ?
N2 C31 H31 118.3 . . ?
C30 C31 N2 123.44(15) . . ?
C30 C31 H31 118.3 . . ?
C38 C43 H43 120.4 . . ?
C38 C43 C42 119.11(16) . . ?
C42 C43 H43 120.4 . . ?
C25 C24 C23 117.61(15) . . ?
C25 C24 C29 120.58(15) . . ?
C29 C24 C23 121.78(14) . . ?
C28 C27 H27 119.8 . . ?
C28 C27 C26 120.45(16) . . ?
C26 C27 H27 119.8 . . ?
C29 C30 C32 121.40(14) . . ?
C31 C30 C29 118.18(15) . . ?
C31 C30 C32 120.41(15) . . ?
C35 O4 C44 116.84(16) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 C29 120.72(16) . . ?
C27 C28 H28 119.6 . . ?
C43 C38 N2 119.89(15) . . ?
C39 C38 N2 119.42(14) . . ?
C39 C38 C43 120.70(16) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C34 C33 C32 121.16(17) . . ?
C25 C26 C27 120.20(16) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C32 C37 H37 119.3 . . ?
C32 C37 C36 121.42(17) . . ?
C36 C37 H37 119.3 . . ?
C33 C32 C30 121.16(15) . . ?
C37 C32 C30 121.12(15) . . ?
C37 C32 C33 117.72(16) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 C38 119.70(16) . . ?
C40 C39 H39 120.2 . . ?
C43 C42 H42 119.7 . . ?
C41 C42 C43 120.62(16) . . ?
C41 C42 H42 119.7 . . ?
O4 C35 C34 115.83(17) . . ?
O4 C35 C36 124.62(17) . . ?
C36 C35 C34 119.55(17) . . ?
C33 C34 C35 120.16(17) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C42 C41 H41 120.2 . . ?
C42 C41 C40 119.65(17) . . ?
C40 C41 H41 120.2 . . ?
C37 C36 H36 120.0 . . ?
C35 C36 C37 119.93(17) . . ?
C35 C36 H36 120.0 . . ?
C39 C40 C41 120.22(17) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 H40 119.9 . . ?
O4 C44 H44A 109.5 . . ?
O4 C44 H44B 109.5 . . ?
O4 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C16 C17 C18 -178.77(15) . . . . ?
O2 C13 C12 C11 -176.80(15) . . . . ?
O2 C13 C14 C15 176.46(14) . . . . ?
C8 C10 C11 C12 -178.62(15) . . . . ?
C8 C10 C15 C14 178.18(15) . . . . ?
C8 C7 C6 C5 179.30(15) . . . . ?
C9 N1 C1 O1 177.78(15) . . . . ?
C9 N1 C1 C2 -3.3(2) . . . . ?
C9 N1 C16 C21 42.2(2) . . . . ?
C9 N1 C16 C17 -138.20(16) . . . . ?
C9 C8 C10 C11 128.33(17) . . . . ?
C9 C8 C10 C15 -50.0(2) . . . . ?
C9 C8 C7 C2 -1.1(2) . . . . ?
C9 C8 C7 C6 178.58(15) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C7 C6 C5 -1.1(2) . . . . ?
C3 C2 C1 O1 0.7(2) . . . . ?
C3 C2 C1 N1 -178.18(14) . . . . ?
C3 C2 C7 C8 -179.69(14) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C1 N1 C9 C8 3.7(2) . . . . ?
C1 N1 C16 C21 -130.63(16) . . . . ?
C1 N1 C16 C17 49.0(2) . . . . ?
C1 C2 C3 C4 179.45(15) . . . . ?
C1 C2 C7 C8 1.2(2) . . . . ?
C1 C2 C7 C6 -178.49(15) . . . . ?
C10 C8 C9 N1 175.91(15) . . . . ?
C10 C8 C7 C2 -178.08(15) . . . . ?
C10 C8 C7 C6 1.6(3) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C7 C8 C9 N1 -1.3(2) . . . . ?
C7 C8 C10 C11 -54.6(2) . . . . ?
C7 C8 C10 C15 126.99(17) . . . . ?
C7 C2 C3 C4 0.3(2) . . . . ?
C7 C2 C1 O1 179.89(16) . . . . ?
C7 C2 C1 N1 1.0(2) . . . . ?
C21 C16 C17 C18 0.8(2) . . . . ?
C21 C20 C19 C18 0.9(2) . . . . ?
C16 N1 C9 C8 -169.12(15) . . . . ?
C16 N1 C1 O1 -9.7(2) . . . . ?
C16 N1 C1 C2 169.26(14) . . . . ?
C16 C21 C20 C19 -1.4(2) . . . . ?
C16 C17 C18 C19 -1.3(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C13 C14 C15 C10 1.3(2) . . . . ?
C12 C13 C14 C15 -1.8(2) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C14 C13 C12 C11 1.3(2) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C20 C21 C16 N1 -179.89(14) . . . . ?
C20 C21 C16 C17 0.5(2) . . . . ?
C6 C5 C4 C3 0.4(3) . . . . ?
C22 O2 C13 C12 -5.6(2) . . . . ?
C22 O2 C13 C14 176.16(16) . . . . ?
O3 C23 C24 C25 5.0(2) . . . . ?
O3 C23 C24 C29 -172.84(16) . . . . ?
N2 C23 C24 C25 -176.31(14) . . . . ?
N2 C23 C24 C29 5.8(2) . . . . ?
N2 C31 C30 C29 1.0(2) . . . . ?
N2 C31 C30 C32 -179.73(15) . . . . ?
N2 C38 C39 C40 179.07(16) . . . . ?
C23 N2 C31 C30 2.5(3) . . . . ?
C23 N2 C38 C43 122.46(17) . . . . ?
C23 N2 C38 C39 -57.9(2) . . . . ?
C29 C30 C32 C33 61.4(2) . . . . ?
C29 C30 C32 C37 -118.93(18) . . . . ?
C31 N2 C23 O3 173.05(16) . . . . ?
C31 N2 C23 C24 -5.7(2) . . . . ?
C31 N2 C38 C43 -55.6(2) . . . . ?
C31 N2 C38 C39 124.09(17) . . . . ?
C31 C30 C32 C33 -117.92(19) . . . . ?
C31 C30 C32 C37 61.8(2) . . . . ?
C43 C38 C39 C40 -1.3(3) . . . . ?
C43 C42 C41 C40 -0.7(3) . . . . ?
C24 C25 C26 C27 2.0(3) . . . . ?
C24 C29 C30 C31 -0.7(2) . . . . ?
C24 C29 C30 C32 179.98(15) . . . . ?
C24 C29 C28 C27 2.3(2) . . . . ?
C30 C29 C24 C23 -2.8(2) . . . . ?
C30 C29 C24 C25 179.40(15) . . . . ?
C30 C29 C28 C27 -179.59(15) . . . . ?
O4 C35 C34 C33 177.21(15) . . . . ?
O4 C35 C36 C37 -177.90(16) . . . . ?
C28 C29 C24 C23 175.40(15) . . . . ?
C28 C29 C24 C25 -2.4(2) . . . . ?
C28 C29 C30 C31 -178.81(16) . . . . ?
C28 C29 C30 C32 1.9(2) . . . . ?
C28 C27 C26 C25 -2.1(3) . . . . ?
C38 N2 C23 O3 -4.9(2) . . . . ?
C38 N2 C23 C24 176.37(14) . . . . ?
C38 N2 C31 C30 -179.54(16) . . . . ?
C38 C43 C42 C41 0.4(3) . . . . ?
C38 C39 C40 C41 1.0(3) . . . . ?
C26 C25 C24 C23 -177.59(15) . . . . ?
C26 C25 C24 C29 0.3(2) . . . . ?
C26 C27 C28 C29 -0.1(3) . . . . ?
C32 C33 C34 C35 1.5(3) . . . . ?
C32 C37 C36 C35 -0.1(3) . . . . ?
C42 C43 C38 N2 -179.77(15) . . . . ?
C42 C43 C38 C39 0.5(3) . . . . ?
C42 C41 C40 C39 0.0(3) . . . . ?
C34 C33 C32 C30 -179.65(15) . . . . ?
C34 C33 C32 C37 0.6(2) . . . . ?
C34 C35 C36 C37 2.3(3) . . . . ?
C36 C37 C32 C30 178.97(15) . . . . ?
C36 C37 C32 C33 -1.3(2) . . . . ?
C36 C35 C34 C33 -2.9(3) . . . . ?
C44 O4 C35 C34 -158.90(16) . . . . ?
C44 O4 C35 C36 21.2(2) . . . . ?

####################################################################### 
# 
# 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_6516
_database_code_depnum_ccdc_archive 'CCDC 2087612'
loop_
_audit_author_name
_audit_author_address
Fan
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-14
_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 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.8247(4)
_cell_length_b                   11.5912(3)
_cell_length_c                   15.5420(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.987(3)
_cell_angle_gamma                90.00
_cell_volume                     2644.75(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3857
_cell_measurement_temperature    112.15(10)
_cell_measurement_theta_max      29.3230
_cell_measurement_theta_min      3.9630
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90182
_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    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14473
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.18
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112.15(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.8395
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -32.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   37.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega   17.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772    0.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega    9.00   36.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   57.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00  -15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772    0.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega  -23.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -99.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000  -60.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0292326000
_diffrn_orient_matrix_UB_12      -0.0455920000
_diffrn_orient_matrix_UB_13      -0.0167032000
_diffrn_orient_matrix_UB_21      -0.0293734000
_diffrn_orient_matrix_UB_22      0.0403434000
_diffrn_orient_matrix_UB_23      -0.0240758000
_diffrn_orient_matrix_UB_31      0.0248616000
_diffrn_orient_matrix_UB_32      -0.0059703000
_diffrn_orient_matrix_UB_33      -0.0355816000
_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                3861
_reflns_number_total             5185
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.233
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.032
_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)+(0.0443P)²+0.4818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1104
_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 0.74210(7) 0.94347(9) 0.15055(7) 0.0238(3) Uani 1 1 d . . .
O2 O 0.25125(7) 0.78082(9) 0.34364(7) 0.0212(3) Uani 1 1 d . . .
N2 N 0.25594(8) 0.96080(10) 0.28190(8) 0.0178(3) Uani 1 1 d . . .
N1 N 0.74164(8) 0.76325(11) 0.21248(8) 0.0189(3) Uani 1 1 d . . .
C26 C 0.52463(10) 0.92072(13) 0.36287(10) 0.0214(4) Uani 1 1 d . . .
H26 H 0.5450 0.8634 0.4028 0.026 Uiso 1 1 calc R . .
C25 C 0.43617(10) 0.96119(13) 0.35641(10) 0.0179(3) Uani 1 1 d . . .
C20 C 0.36245(10) 0.92158(13) 0.41053(10) 0.0183(3) Uani 1 1 d . . .
C11 C 0.53613(11) 0.63651(13) 0.26463(10) 0.0225(4) Uani 1 1 d . . .
H11 H 0.5586 0.5812 0.3054 0.027 Uiso 1 1 calc R . .
C31 C 0.19932(10) 0.93761(13) 0.20175(10) 0.0173(3) Uani 1 1 d . . .
C13 C 0.80220(10) 0.78801(13) 0.28981(10) 0.0187(3) Uani 1 1 d . . .
C7 C 0.55839(10) 0.76542(13) 0.14716(10) 0.0189(3) Uani 1 1 d . . .
C19 C 0.28346(10) 0.87808(13) 0.34255(9) 0.0169(3) Uani 1 1 d . . .
C24 C 0.40596(10) 1.04519(13) 0.29499(10) 0.0179(3) Uani 1 1 d . . .
C6 C 0.59103(10) 0.68200(13) 0.20810(10) 0.0186(3) Uani 1 1 d . . .
C8 C 0.47012(10) 0.80571(14) 0.14324(10) 0.0218(4) Uani 1 1 d . . .
H8 H 0.4483 0.8630 0.1039 0.026 Uiso 1 1 calc R . .
C29 C 0.46313(11) 1.09104(13) 0.24079(10) 0.0217(4) Uani 1 1 d . . .
H29 H 0.4422 1.1471 0.2000 0.026 Uiso 1 1 calc R . .
C2 C 0.62881(10) 0.80233(13) 0.08842(10) 0.0198(3) Uani 1 1 d . . .
C23 C 0.30575(10) 1.07302(13) 0.29575(10) 0.0183(3) Uani 1 1 d . . .
H23 H 0.2830 1.1313 0.2524 0.022 Uiso 1 1 calc R . .
C5 C 0.68991(10) 0.65213(13) 0.20256(10) 0.0200(3) Uani 1 1 d . . .
H5 H 0.7143 0.5943 0.2456 0.024 Uiso 1 1 calc R . .
C10 C 0.44656(11) 0.67494(14) 0.25942(11) 0.0251(4) Uani 1 1 d . . .
H10 H 0.4083 0.6443 0.2962 0.030 Uiso 1 1 calc R . .
C36 C 0.11940(10) 0.87478(13) 0.19978(10) 0.0212(4) Uani 1 1 d . . .
H36 H 0.1023 0.8466 0.2512 0.025 Uiso 1 1 calc R . .
C27 C 0.58280(10) 0.96723(14) 0.30863(11) 0.0244(4) Uani 1 1 d . . .
H27 H 0.6426 0.9411 0.3130 0.029 Uiso 1 1 calc R . .
C32 C 0.22389(11) 0.97950(14) 0.12444(10) 0.0243(4) Uani 1 1 d . . .
H32 H 0.2775 1.0213 0.1253 0.029 Uiso 1 1 calc R . .
C16 C 0.91978(11) 0.83668(14) 0.44115(11) 0.0276(4) Uani 1 1 d . . .
H16 H 0.9589 0.8533 0.4918 0.033 Uiso 1 1 calc R . .
C28 C 0.55286(11) 1.05170(14) 0.24840(11) 0.0249(4) Uani 1 1 d . . .
H28 H 0.5926 1.0823 0.2130 0.030 Uiso 1 1 calc R . .
C21 C 0.32456(10) 1.03189(13) 0.44664(10) 0.0205(3) Uani 1 1 d . . .
H21 H 0.3217 1.0426 0.5055 0.025 Uiso 1 1 calc R . .
C15 C 0.84191(11) 0.77181(15) 0.44445(11) 0.0279(4) Uani 1 1 d . . .
H15 H 0.8292 0.7439 0.4976 0.034 Uiso 1 1 calc R . .
C14 C 0.78276(11) 0.74805(14) 0.36966(10) 0.0233(4) Uani 1 1 d . . .
H14 H 0.7301 0.7055 0.3727 0.028 Uiso 1 1 calc R . .
C1 C 0.71102(10) 0.84574(13) 0.15286(10) 0.0183(3) Uani 1 1 d . . .
C12 C 0.59707(11) 0.89261(15) 0.02094(10) 0.0276(4) Uani 1 1 d . . .
H12A H 0.5450 0.8642 -0.0168 0.041 Uiso 1 1 calc R . .
H12B H 0.6452 0.9094 -0.0125 0.041 Uiso 1 1 calc R . .
H12C H 0.5807 0.9616 0.0493 0.041 Uiso 1 1 calc R . .
C34 C 0.08943(11) 0.89637(14) 0.04453(11) 0.0283(4) Uani 1 1 d . . .
H34 H 0.0525 0.8826 -0.0079 0.034 Uiso 1 1 calc R . .
C30 C 0.39372(11) 0.83066(14) 0.47835(10) 0.0235(4) Uani 1 1 d . . .
H30A H 0.4128 0.7629 0.4503 0.035 Uiso 1 1 calc R . .
H30B H 0.3444 0.8114 0.5097 0.035 Uiso 1 1 calc R . .
H30C H 0.4438 0.8602 0.5180 0.035 Uiso 1 1 calc R . .
C3 C 0.66242(10) 0.69021(14) 0.05110(11) 0.0235(4) Uani 1 1 d . . .
H3 H 0.6614 0.6781 -0.0082 0.028 Uiso 1 1 calc R . .
C4 C 0.69289(10) 0.61239(14) 0.10997(10) 0.0233(4) Uani 1 1 d . . .
H4 H 0.7141 0.5402 0.0961 0.028 Uiso 1 1 calc R . .
C22 C 0.29638(10) 1.11008(13) 0.38767(10) 0.0200(3) Uani 1 1 d . . .
H22 H 0.2730 1.1813 0.4010 0.024 Uiso 1 1 calc R . .
C18 C 0.88103(10) 0.85152(13) 0.28608(10) 0.0215(4) Uani 1 1 d . . .
H18 H 0.8950 0.8772 0.2328 0.026 Uiso 1 1 calc R . .
C9 C 0.41444(10) 0.75869(14) 0.19955(11) 0.0251(4) Uani 1 1 d . . .
H9 H 0.3546 0.7841 0.1968 0.030 Uiso 1 1 calc R . .
C17 C 0.93885(11) 0.87662(14) 0.36159(11) 0.0263(4) Uani 1 1 d . . .
H17 H 0.9909 0.9206 0.3589 0.032 Uiso 1 1 calc R . .
C35 C 0.06507(11) 0.85402(14) 0.12143(11) 0.0265(4) Uani 1 1 d . . .
H35 H 0.0118 0.8113 0.1204 0.032 Uiso 1 1 calc R . .
C33 C 0.16908(11) 0.95935(15) 0.04626(11) 0.0292(4) Uani 1 1 d . . .
H33 H 0.1857 0.9881 -0.0051 0.035 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 C1 1.2253(18) . ?
O2 C19 1.2253(17) . ?
N2 C31 1.4276(18) . ?
N2 C19 1.3666(19) . ?
N2 C23 1.4964(19) . ?
N1 C13 1.4258(19) . ?
N1 C5 1.4960(19) . ?
N1 C1 1.3645(19) . ?
C26 H26 0.9300 . ?
C26 C25 1.383(2) . ?
C26 C27 1.395(2) . ?
C25 C20 1.539(2) . ?
C25 C24 1.393(2) . ?
C20 C19 1.548(2) . ?
C20 C21 1.534(2) . ?
C20 C30 1.517(2) . ?
C11 H11 0.9300 . ?
C11 C6 1.382(2) . ?
C11 C10 1.392(2) . ?
C31 C36 1.387(2) . ?
C31 C32 1.391(2) . ?
C13 C14 1.392(2) . ?
C13 C18 1.389(2) . ?
C7 C6 1.392(2) . ?
C7 C8 1.383(2) . ?
C7 C2 1.540(2) . ?
C24 C29 1.382(2) . ?
C24 C23 1.522(2) . ?
C6 C5 1.520(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(2) . ?
C29 H29 0.9300 . ?
C29 C28 1.396(2) . ?
C2 C1 1.550(2) . ?
C2 C12 1.510(2) . ?
C2 C3 1.534(2) . ?
C23 H23 0.9800 . ?
C23 C22 1.517(2) . ?
C5 H5 0.9800 . ?
C5 C4 1.517(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.383(2) . ?
C36 H36 0.9300 . ?
C36 C35 1.384(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(2) . ?
C32 H32 0.9300 . ?
C32 C33 1.384(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.385(2) . ?
C16 C17 1.386(2) . ?
C28 H28 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.315(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.383(2) . ?
C14 H14 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C34 H34 0.9300 . ?
C34 C35 1.386(2) . ?
C34 C33 1.385(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.319(2) . ?
C4 H4 0.9300 . ?
C22 H22 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.385(2) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C35 H35 0.9300 . ?
C33 H33 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
C31 N2 C23 120.51(12) . . ?
C19 N2 C31 123.56(12) . . ?
C19 N2 C23 114.62(12) . . ?
C13 N1 C5 120.92(12) . . ?
C1 N1 C13 122.85(13) . . ?
C1 N1 C5 114.58(12) . . ?
C25 C26 H26 120.5 . . ?
C25 C26 C27 118.97(15) . . ?
C27 C26 H26 120.5 . . ?
C26 C25 C20 126.67(14) . . ?
C26 C25 C24 119.88(13) . . ?
C24 C25 C20 113.44(13) . . ?
C25 C20 C19 104.56(11) . . ?
C21 C20 C25 105.98(12) . . ?
C21 C20 C19 103.91(12) . . ?
C30 C20 C25 114.54(12) . . ?
C30 C20 C19 112.15(12) . . ?
C30 C20 C21 114.65(13) . . ?
C6 C11 H11 120.6 . . ?
C6 C11 C10 118.82(15) . . ?
C10 C11 H11 120.6 . . ?
C36 C31 N2 120.98(13) . . ?
C36 C31 C32 119.31(14) . . ?
C32 C31 N2 119.70(13) . . ?
C14 C13 N1 120.03(14) . . ?
C18 C13 N1 120.42(13) . . ?
C18 C13 C14 119.55(15) . . ?
C6 C7 C2 113.33(13) . . ?
C8 C7 C6 120.11(14) . . ?
C8 C7 C2 126.55(14) . . ?
O2 C19 N2 125.14(14) . . ?
O2 C19 C20 123.32(14) . . ?
N2 C19 C20 111.54(12) . . ?
C25 C24 C23 111.35(12) . . ?
C29 C24 C25 121.37(14) . . ?
C29 C24 C23 127.26(14) . . ?
C11 C6 C7 121.17(14) . . ?
C11 C6 C5 127.35(14) . . ?
C7 C6 C5 111.48(13) . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.65(15) . . ?
C9 C8 H8 120.7 . . ?
C24 C29 H29 120.6 . . ?
C24 C29 C28 118.74(15) . . ?
C28 C29 H29 120.6 . . ?
C7 C2 C1 104.13(12) . . ?
C12 C2 C7 115.65(13) . . ?
C12 C2 C1 111.41(13) . . ?
C12 C2 C3 114.25(13) . . ?
C3 C2 C7 105.74(12) . . ?
C3 C2 C1 104.59(12) . . ?
N2 C23 C24 106.10(12) . . ?
N2 C23 H23 112.6 . . ?
N2 C23 C22 105.89(11) . . ?
C24 C23 H23 112.6 . . ?
C22 C23 C24 106.54(12) . . ?
C22 C23 H23 112.6 . . ?
N1 C5 C6 106.42(12) . . ?
N1 C5 H5 112.6 . . ?
N1 C5 C4 106.08(12) . . ?
C6 C5 H5 112.6 . . ?
C4 C5 C6 106.16(13) . . ?
C4 C5 H5 112.6 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.01(14) . . ?
C9 C10 H10 120.0 . . ?
C31 C36 H36 120.0 . . ?
C35 C36 C31 120.09(14) . . ?
C35 C36 H36 120.0 . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 120.98(14) . . ?
C28 C27 H27 119.5 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.48(14) . . ?
C33 C32 H32 119.8 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.27(16) . . ?
C17 C16 H16 120.4 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 C29 120.04(14) . . ?
C27 C28 H28 120.0 . . ?
C20 C21 H21 122.7 . . ?
C22 C21 C20 114.62(13) . . ?
C22 C21 H21 122.7 . . ?
C16 C15 H15 119.6 . . ?
C14 C15 C16 120.77(16) . . ?
C14 C15 H15 119.6 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.83(15) . . ?
C15 C14 H14 120.1 . . ?
O1 C1 N1 125.22(14) . . ?
O1 C1 C2 123.11(14) . . ?
N1 C1 C2 111.64(13) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.58(16) . . ?
C20 C30 H30A 109.5 . . ?
C20 C30 H30B 109.5 . . ?
C20 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C2 C3 H3 122.7 . . ?
C4 C3 C2 114.51(14) . . ?
C4 C3 H3 122.7 . . ?
C5 C4 H4 123.3 . . ?
C3 C4 C5 113.45(14) . . ?
C3 C4 H4 123.3 . . ?
C23 C22 H22 123.2 . . ?
C21 C22 C23 113.54(13) . . ?
C21 C22 H22 123.2 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.09(15) . . ?
C17 C18 H18 120.0 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.21(14) . . ?
C10 C9 H9 119.4 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.47(15) . . ?
C18 C17 H17 119.8 . . ?
C36 C35 C34 120.50(15) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C32 C33 C34 120.04(15) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C31 C36 C35 179.48(14) . . . . ?
N2 C31 C32 C33 -179.00(14) . . . . ?
N2 C23 C22 C21 55.02(16) . . . . ?
N1 C13 C14 C15 179.70(14) . . . . ?
N1 C13 C18 C17 179.08(13) . . . . ?
N1 C5 C4 C3 -54.95(16) . . . . ?
C26 C25 C20 C19 -121.74(16) . . . . ?
C26 C25 C20 C21 128.82(16) . . . . ?
C26 C25 C20 C30 1.4(2) . . . . ?
C26 C25 C24 C29 -1.1(2) . . . . ?
C26 C25 C24 C23 177.17(13) . . . . ?
C26 C27 C28 C29 -0.5(2) . . . . ?
C25 C26 C27 C28 -0.7(2) . . . . ?
C25 C20 C19 O2 123.95(14) . . . . ?
C25 C20 C19 N2 -55.34(15) . . . . ?
C25 C20 C21 C22 53.47(17) . . . . ?
C25 C24 C29 C28 0.0(2) . . . . ?
C25 C24 C23 N2 -55.67(15) . . . . ?
C25 C24 C23 C22 56.84(16) . . . . ?
C20 C25 C24 C29 179.81(13) . . . . ?
C20 C25 C24 C23 -1.88(18) . . . . ?
C20 C21 C22 C23 1.17(18) . . . . ?
C11 C6 C5 N1 -124.33(16) . . . . ?
C11 C6 C5 C4 122.96(16) . . . . ?
C11 C10 C9 C8 0.4(2) . . . . ?
C31 N2 C19 O2 -13.6(2) . . . . ?
C31 N2 C19 C20 165.64(12) . . . . ?
C31 N2 C23 C24 -108.95(14) . . . . ?
C31 N2 C23 C22 138.09(13) . . . . ?
C31 C36 C35 C34 -0.5(2) . . . . ?
C31 C32 C33 C34 -0.5(2) . . . . ?
C13 N1 C5 C6 108.45(14) . . . . ?
C13 N1 C5 C4 -138.80(13) . . . . ?
C13 N1 C1 O1 12.7(2) . . . . ?
C13 N1 C1 C2 -165.63(12) . . . . ?
C13 C18 C17 C16 1.4(2) . . . . ?
C7 C6 C5 N1 55.42(16) . . . . ?
C7 C6 C5 C4 -57.29(16) . . . . ?
C7 C8 C9 C10 1.2(2) . . . . ?
C7 C2 C1 O1 -121.93(15) . . . . ?
C7 C2 C1 N1 56.43(15) . . . . ?
C7 C2 C3 C4 -53.68(17) . . . . ?
C19 N2 C31 C36 49.34(19) . . . . ?
C19 N2 C31 C32 -131.35(15) . . . . ?
C19 N2 C23 C24 58.44(15) . . . . ?
C19 N2 C23 C22 -54.52(15) . . . . ?
C19 C20 C21 C22 -56.42(16) . . . . ?
C24 C25 C20 C19 57.24(15) . . . . ?
C24 C25 C20 C21 -52.20(16) . . . . ?
C24 C25 C20 C30 -179.62(13) . . . . ?
C24 C29 C28 C27 0.8(2) . . . . ?
C24 C23 C22 C21 -57.65(16) . . . . ?
C6 C11 C10 C9 -1.2(2) . . . . ?
C6 C7 C8 C9 -1.8(2) . . . . ?
C6 C7 C2 C1 -57.49(16) . . . . ?
C6 C7 C2 C12 179.93(13) . . . . ?
C6 C7 C2 C3 52.43(17) . . . . ?
C6 C5 C4 C3 57.99(16) . . . . ?
C8 C7 C6 C11 1.1(2) . . . . ?
C8 C7 C6 C5 -178.70(13) . . . . ?
C8 C7 C2 C1 123.30(16) . . . . ?
C8 C7 C2 C12 0.7(2) . . . . ?
C8 C7 C2 C3 -126.77(16) . . . . ?
C29 C24 C23 N2 122.51(16) . . . . ?
C29 C24 C23 C22 -124.97(16) . . . . ?
C2 C7 C6 C11 -178.20(14) . . . . ?
C2 C7 C6 C5 2.03(18) . . . . ?
C2 C7 C8 C9 177.31(14) . . . . ?
C2 C3 C4 C5 -1.26(19) . . . . ?
C23 N2 C31 C36 -144.44(14) . . . . ?
C23 N2 C31 C32 34.87(19) . . . . ?
C23 N2 C19 O2 179.41(13) . . . . ?
C23 N2 C19 C20 -1.31(16) . . . . ?
C23 C24 C29 C28 -178.04(14) . . . . ?
C5 N1 C13 C14 -33.62(19) . . . . ?
C5 N1 C13 C18 146.09(13) . . . . ?
C5 N1 C1 O1 178.15(13) . . . . ?
C5 N1 C1 C2 -0.17(16) . . . . ?
C10 C11 C6 C7 0.5(2) . . . . ?
C10 C11 C6 C5 -179.81(15) . . . . ?
C36 C31 C32 C33 0.3(2) . . . . ?
C27 C26 C25 C20 -179.60(14) . . . . ?
C27 C26 C25 C24 1.5(2) . . . . ?
C32 C31 C36 C35 0.2(2) . . . . ?
C16 C15 C14 C13 1.1(2) . . . . ?
C21 C20 C19 O2 -125.12(14) . . . . ?
C21 C20 C19 N2 55.59(14) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C14 C13 C18 C17 -1.2(2) . . . . ?
C1 N1 C13 C14 130.94(15) . . . . ?
C1 N1 C13 C18 -49.35(19) . . . . ?
C1 N1 C5 C6 -57.32(15) . . . . ?
C1 N1 C5 C4 55.44(15) . . . . ?
C1 C2 C3 C4 55.92(16) . . . . ?
C12 C2 C1 O1 3.4(2) . . . . ?
C12 C2 C1 N1 -178.25(12) . . . . ?
C12 C2 C3 C4 177.99(13) . . . . ?
C30 C20 C19 O2 -0.73(19) . . . . ?
C30 C20 C19 N2 179.98(12) . . . . ?
C30 C20 C21 C22 -179.17(13) . . . . ?
C3 C2 C1 O1 127.31(15) . . . . ?
C3 C2 C1 N1 -54.33(15) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C17 C16 C15 C14 -0.9(2) . . . . ?
C35 C34 C33 C32 0.1(2) . . . . ?
C33 C34 C35 C36 0.4(2) . . . . ?

