# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_5725
_database_code_depnum_ccdc_archive 'CCDC 1983900'
loop_
_audit_author_name
_audit_author_address
'Pengyu Li'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2020-02-13 deposited with the CCDC.	2020-11-18 downloaded from the CCDC.
;
_audit_creation_date             2018-12-13
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        CSPr
_chemical_formula_moiety         'C23 H23 N O4'
_chemical_formula_sum            'C23 H23 N O4'
_chemical_formula_weight         377.42
_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                   6.6609(7)
_cell_length_b                   7.3282(7)
_cell_length_c                   21.588(2)
_cell_angle_alpha                85.693(9)
_cell_angle_beta                 83.663(9)
_cell_angle_gamma                69.364(9)
_cell_volume                     979.40(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2457
_cell_measurement_temperature    110.1(9)
_cell_measurement_theta_max      28.7360
_cell_measurement_theta_min      3.5230
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89845
_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            white
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7347
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.09
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.1(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.8344
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega   51.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335 -178.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -57.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
  4 omega    6.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000  -30.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega  -19.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega  -49.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -37.0000 -120.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0982641000
_diffrn_orient_matrix_UB_12      -0.0161115000
_diffrn_orient_matrix_UB_13      -0.0015820000
_diffrn_orient_matrix_UB_21      0.0060674000
_diffrn_orient_matrix_UB_22      0.0206532000
_diffrn_orient_matrix_UB_23      -0.0326535000
_diffrn_orient_matrix_UB_31      0.0580565000
_diffrn_orient_matrix_UB_32      -0.1000999000
_diffrn_orient_matrix_UB_33      -0.0051411000
_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                3199
_reflns_number_total             3835
_reflns_odcompleteness_completeness 99.80
_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         0.246
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.031
_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)+(0.0396P)²+0.3255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1041
_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
O4 O 0.47529(15) 0.65509(15) 0.28402(5) 0.0201(2) Uani 1 1 d . . .
O3 O 0.83749(16) 0.52680(16) 0.28068(5) 0.0259(3) Uani 1 1 d . . .
O2 O 0.73572(16) 0.85930(15) 0.88420(5) 0.0220(3) Uani 1 1 d . . .
O1 O 0.38170(17) 1.02022(17) 0.90637(5) 0.0290(3) Uani 1 1 d . . .
C9 C 0.6623(2) 0.7855(2) 0.70159(7) 0.0188(3) Uani 1 1 d . . .
H9 H 0.7843 0.7198 0.6742 0.023 Uiso 1 1 calc R . .
C7 C 0.5116(2) 0.9081(2) 0.80330(7) 0.0175(3) Uani 1 1 d . . .
C2 C 0.4258(2) 0.8273(2) 0.61416(7) 0.0184(3) Uani 1 1 d . . .
N1 N 0.0320(2) 0.8785(2) 0.59460(6) 0.0289(3) Uani 1 1 d . . .
C21 C 0.4852(2) 0.6084(2) 0.21918(7) 0.0185(3) Uani 1 1 d . . .
H21A H 0.5423 0.4652 0.2147 0.022 Uiso 1 1 calc R . .
H21B H 0.5802 0.6660 0.1926 0.022 Uiso 1 1 calc R . .
C14 C 0.6341(2) 0.6593(2) 0.37552(7) 0.0180(3) Uani 1 1 d . . .
C3 C 0.5867(2) 0.7841(2) 0.56805(7) 0.0200(3) Uani 1 1 d . . .
H3 H 0.7219 0.7767 0.5804 0.024 Uiso 1 1 calc R . .
C4 C 0.4565(2) 0.8540(2) 0.67983(7) 0.0172(3) Uani 1 1 d . . .
C1 C 0.2077(2) 0.8546(2) 0.60239(7) 0.0197(3) Uani 1 1 d . . .
C17 C 0.6646(2) 0.6057(2) 0.30872(7) 0.0178(3) Uani 1 1 d . . .
C6 C 0.3067(2) 0.9742(2) 0.78225(7) 0.0201(3) Uani 1 1 d . . .
H6 H 0.1848 1.0385 0.8099 0.024 Uiso 1 1 calc R . .
C5 C 0.2794(2) 0.9468(2) 0.72131(7) 0.0205(3) Uani 1 1 d . . .
H5 H 0.1387 0.9918 0.7076 0.025 Uiso 1 1 calc R . .
C8 C 0.6894(2) 0.8128(2) 0.76254(7) 0.0182(3) Uani 1 1 d . . .
H8 H 0.8295 0.7664 0.7766 0.022 Uiso 1 1 calc R . .
C13 C 0.4328(2) 0.7178(2) 0.40884(7) 0.0220(3) Uani 1 1 d . . .
H13 H 0.3092 0.7290 0.3886 0.026 Uiso 1 1 calc R . .
C15 C 0.8140(2) 0.6493(2) 0.40514(7) 0.0208(3) Uani 1 1 d . . .
H15 H 0.9523 0.6111 0.3827 0.025 Uiso 1 1 calc R . .
C16 C 0.7908(2) 0.6952(2) 0.46713(7) 0.0201(3) Uani 1 1 d . . .
H16 H 0.9136 0.6917 0.4865 0.024 Uiso 1 1 calc R . .
C22 C 0.2574(2) 0.6936(2) 0.20040(7) 0.0207(3) Uani 1 1 d . . .
H22A H 0.2024 0.8363 0.2057 0.025 Uiso 1 1 calc R . .
H22B H 0.1642 0.6369 0.2282 0.025 Uiso 1 1 calc R . .
C11 C 0.5903(2) 0.7465(2) 0.50196(7) 0.0190(3) Uani 1 1 d . . .
C10 C 0.5315(2) 0.9372(2) 0.86971(7) 0.0188(3) Uani 1 1 d . . .
C18 C 0.7711(2) 0.8581(2) 0.94972(7) 0.0233(3) Uani 1 1 d . . .
H18A H 0.7136 0.7653 0.9745 0.028 Uiso 1 1 calc R . .
H18B H 0.6972 0.9897 0.9664 0.028 Uiso 1 1 calc R . .
C23 C 0.2450(3) 0.6534(2) 0.13289(7) 0.0271(4) Uani 1 1 d . . .
H23A H 0.3383 0.7080 0.1053 0.041 Uiso 1 1 calc R . .
H23B H 0.0960 0.7140 0.1221 0.041 Uiso 1 1 calc R . .
H23C H 0.2926 0.5122 0.1279 0.041 Uiso 1 1 calc R . .
C12 C 0.4097(2) 0.7601(2) 0.47115(7) 0.0241(4) Uani 1 1 d . . .
H12 H 0.2709 0.7986 0.4933 0.029 Uiso 1 1 calc R . .
C19 C 1.0102(3) 0.7970(2) 0.95345(7) 0.0279(4) Uani 1 1 d . . .
H19A H 1.0384 0.7894 0.9978 0.033 Uiso 1 1 calc R . .
H19B H 1.0614 0.8987 0.9319 0.033 Uiso 1 1 calc R . .
C20 C 1.1389(3) 0.6023(3) 0.92491(9) 0.0396(5) Uani 1 1 d . . .
H20A H 1.1239 0.6122 0.8800 0.059 Uiso 1 1 calc R . .
H20B H 1.0847 0.5015 0.9445 0.059 Uiso 1 1 calc R . .
H20C H 1.2911 0.5674 0.9318 0.059 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
O4 C21 1.4549(16) . ?
O4 C17 1.3431(17) . ?
O3 C17 1.2066(17) . ?
O2 C10 1.3394(17) . ?
O2 C18 1.4582(17) . ?
O1 C10 1.2094(17) . ?
C9 H9 0.9500 . ?
C9 C4 1.405(2) . ?
C9 C8 1.3860(19) . ?
C7 C6 1.393(2) . ?
C7 C8 1.394(2) . ?
C7 C10 1.4920(19) . ?
C2 C3 1.346(2) . ?
C2 C4 1.4914(19) . ?
C2 C1 1.444(2) . ?
N1 C1 1.1502(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.512(2) . ?
C14 C17 1.4962(19) . ?
C14 C13 1.388(2) . ?
C14 C15 1.397(2) . ?
C3 H3 0.9500 . ?
C3 C11 1.4693(19) . ?
C4 C5 1.396(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(2) . ?
C16 H16 0.9500 . ?
C16 C11 1.399(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.525(2) . ?
C11 C12 1.408(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.504(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C12 H12 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.518(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C17 O4 C21 116.33(11) . . ?
C10 O2 C18 116.66(11) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C4 120.76(13) . . ?
C6 C7 C8 119.32(13) . . ?
C6 C7 C10 118.35(13) . . ?
C8 C7 C10 122.30(13) . . ?
C3 C2 C4 123.44(13) . . ?
C3 C2 C1 121.28(13) . . ?
C1 C2 C4 115.27(12) . . ?
O4 C21 H21A 110.4 . . ?
O4 C21 H21B 110.4 . . ?
O4 C21 C22 106.57(11) . . ?
H21A C21 H21B 108.6 . . ?
C22 C21 H21A 110.4 . . ?
C22 C21 H21B 110.4 . . ?
C13 C14 C17 122.01(13) . . ?
C13 C14 C15 119.16(13) . . ?
C15 C14 C17 118.82(13) . . ?
C2 C3 H3 114.3 . . ?
C2 C3 C11 131.47(13) . . ?
C11 C3 H3 114.3 . . ?
C9 C4 C2 121.19(13) . . ?
C5 C4 C9 118.50(13) . . ?
C5 C4 C2 120.31(13) . . ?
N1 C1 C2 178.13(15) . . ?
O4 C17 C14 111.47(12) . . ?
O3 C17 O4 124.22(13) . . ?
O3 C17 C14 124.31(13) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.52(13) . . ?
C5 C6 H6 119.7 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.68(13) . . ?
C6 C5 H5 119.7 . . ?
C9 C8 C7 120.21(13) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 120.90(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.04(14) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C11 121.37(13) . . ?
C11 C16 H16 119.3 . . ?
C21 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C21 C22 C23 111.90(12) . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C16 C11 C3 116.59(12) . . ?
C16 C11 C12 117.93(13) . . ?
C12 C11 C3 125.48(14) . . ?
O2 C10 C7 111.93(12) . . ?
O1 C10 O2 123.74(13) . . ?
O1 C10 C7 124.32(13) . . ?
O2 C18 H18A 110.2 . . ?
O2 C18 H18B 110.2 . . ?
O2 C18 C19 107.35(12) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C12 C11 120.52(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C18 C19 C20 114.03(14) . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C21 C22 C23 -179.63(12) . . . . ?
O2 C18 C19 C20 -55.96(18) . . . . ?
C9 C4 C5 C6 1.2(2) . . . . ?
C7 C6 C5 C4 -0.5(2) . . . . ?
C2 C3 C11 C16 -176.72(15) . . . . ?
C2 C3 C11 C12 4.0(3) . . . . ?
C2 C4 C5 C6 -179.28(14) . . . . ?
C21 O4 C17 O3 0.0(2) . . . . ?
C21 O4 C17 C14 -179.51(11) . . . . ?
C14 C13 C12 C11 0.7(2) . . . . ?
C14 C15 C16 C11 1.9(2) . . . . ?
C3 C2 C4 C9 -17.3(2) . . . . ?
C3 C2 C4 C5 163.19(14) . . . . ?
C3 C2 C1 N1 -168(5) . . . . ?
C3 C11 C12 C13 -178.83(14) . . . . ?
C4 C9 C8 C7 0.3(2) . . . . ?
C4 C2 C3 C11 177.77(14) . . . . ?
C4 C2 C1 N1 11(6) . . . . ?
C1 C2 C3 C11 -3.4(3) . . . . ?
C1 C2 C4 C9 163.81(13) . . . . ?
C1 C2 C4 C5 -15.7(2) . . . . ?
C17 O4 C21 C22 -174.86(12) . . . . ?
C17 C14 C13 C12 177.75(14) . . . . ?
C17 C14 C15 C16 -179.03(13) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C6 C7 C10 O2 177.29(13) . . . . ?
C6 C7 C10 O1 -2.4(2) . . . . ?
C8 C9 C4 C2 179.35(13) . . . . ?
C8 C9 C4 C5 -1.2(2) . . . . ?
C8 C7 C6 C5 -0.4(2) . . . . ?
C8 C7 C10 O2 -0.9(2) . . . . ?
C8 C7 C10 O1 179.39(15) . . . . ?
C13 C14 C17 O4 11.1(2) . . . . ?
C13 C14 C17 O3 -168.38(15) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C15 C14 C17 O4 -169.08(13) . . . . ?
C15 C14 C17 O3 11.4(2) . . . . ?
C15 C14 C13 C12 -2.1(2) . . . . ?
C15 C16 C11 C3 177.48(14) . . . . ?
C15 C16 C11 C12 -3.2(2) . . . . ?
C16 C11 C12 C13 1.9(2) . . . . ?
C10 O2 C18 C19 -170.56(13) . . . . ?
C10 C7 C6 C5 -178.62(13) . . . . ?
C10 C7 C8 C9 178.61(13) . . . . ?
C18 O2 C10 O1 6.9(2) . . . . ?
C18 O2 C10 C7 -172.80(12) . . . . ?

_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_5493
_database_code_depnum_ccdc_archive 'CCDC 1983911'
loop_
_audit_author_name
_audit_author_address
'Pengyu Li'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2020-02-13 deposited with the CCDC.	2020-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.8112(11)
_cell_length_b                   9.4028(11)
_cell_length_c                   11.1812(11)
_cell_angle_alpha                97.718(9)
_cell_angle_beta                 108.562(10)
_cell_angle_gamma                93.381(10)
_cell_volume                     865.11(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6190
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3396
_reflns_number_gt                2750
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.7346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3396
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.09654(18) 0.79242(16) 0.77039(13) 0.0267(4) Uani 1 1 d . . .
O4 O 0.58975(18) 0.04493(15) 1.78708(13) 0.0266(4) Uani 1 1 d . . .
O1 O 0.30278(19) 0.67504(17) 0.74406(14) 0.0323(4) Uani 1 1 d . . .
C9 C 0.2087(2) 0.7007(2) 0.80101(19) 0.0224(4) Uani 1 1 d . . .
C6 C 0.2076(2) 0.6388(2) 0.91668(18) 0.0217(4) Uani 1 1 d . . .
C8 C 0.3083(3) 0.4741(2) 1.0650(2) 0.0308(5) Uani 1 1 d . . .
H8 H 0.3679 0.3975 1.0866 0.037 Uiso 1 1 calc R . .
C14 C 0.4440(2) 0.2036(2) 1.65933(18) 0.0213(4) Uani 1 1 d . . .
O3 O 0.4015(2) 0.15349(18) 1.85092(14) 0.0349(4) Uani 1 1 d . . .
C1 C 0.1306(3) 0.5415(2) 1.33184(19) 0.0235(5) Uani 1 1 d . . .
C15 C 0.5352(3) 0.1838(2) 1.57757(19) 0.0252(5) Uani 1 1 d . . .
H15 H 0.6181 0.1248 1.5945 0.030 Uiso 1 1 calc R . .
C7 C 0.2975(3) 0.5253(2) 0.9509(2) 0.0279(5) Uani 1 1 d . . .
H7 H 0.3507 0.4831 0.8978 0.033 Uiso 1 1 calc R . .
C11 C 0.3784(3) 0.3409(2) 1.44368(19) 0.0266(5) Uani 1 1 d . . .
C4 C 0.1366(3) 0.6464(2) 1.10912(19) 0.0269(5) Uani 1 1 d . . .
H4 H 0.0806 0.6871 1.1606 0.032 Uiso 1 1 calc R . .
C5 C 0.1252(3) 0.6963(2) 0.99559(19) 0.0236(4) Uani 1 1 d . . .
H5 H 0.0610 0.7696 0.9719 0.028 Uiso 1 1 calc R . .
C17 C 0.4739(2) 0.1337(2) 1.77567(19) 0.0231(4) Uani 1 1 d . . .
C21 C 0.7795(3) -0.0911(2) 1.9142(2) 0.0351(6) Uani 1 1 d . . .
H21A H 0.7688 -0.1587 1.8388 0.053 Uiso 1 1 calc R . .
H21B H 0.8049 -0.1401 1.9870 0.053 Uiso 1 1 calc R . .
H21C H 0.8641 -0.0159 1.9265 0.053 Uiso 1 1 calc R . .
C20 C 0.6248(3) -0.0270(2) 1.8990(2) 0.0287(5) Uani 1 1 d . . .
H20A H 0.5387 -0.1019 1.8877 0.034 Uiso 1 1 calc R . .
H20B H 0.6345 0.0420 1.9745 0.034 Uiso 1 1 calc R . .
C16 C 0.5020(3) 0.2520(2) 1.4717(2) 0.0266(5) Uani 1 1 d . . .
H16 H 0.5634 0.2383 1.4179 0.032 Uiso 1 1 calc R . .
N1 N 0.0376(2) 0.5925(2) 1.37082(18) 0.0342(5) Uani 1 1 d . . .
C18 C 0.0943(3) 0.8682(2) 0.6647(2) 0.0322(5) Uani 1 1 d . . .
H18A H 0.0528 0.8026 0.5841 0.039 Uiso 1 1 calc R . .
H18B H 0.2022 0.9091 0.6746 0.039 Uiso 1 1 calc R . .
C13 C 0.3207(3) 0.2920(2) 1.63343(19) 0.0260(5) Uani 1 1 d . . .
H13 H 0.2598 0.3049 1.6876 0.031 Uiso 1 1 calc R . .
C2 C 0.2436(3) 0.4881(2) 1.2716(2) 0.0269(5) Uani 1 1 d . . .
C12 C 0.2874(3) 0.3612(2) 1.5273(2) 0.0288(5) Uani 1 1 d . . .
H12 H 0.2052 0.4209 1.5111 0.035 Uiso 1 1 calc R . .
C3 C 0.2305(3) 0.5368(2) 1.1466(2) 0.0264(5) Uani 1 1 d . . .
C10 C 0.3539(3) 0.4046(2) 1.3270(2) 0.0281(5) Uani 1 1 d . . .
H10 H 0.4272 0.3833 1.2847 0.034 Uiso 1 1 calc R . .
C19 C -0.0135(4) 0.9859(3) 0.6679(2) 0.0492(7) Uani 1 1 d . . .
H19A H -0.1202 0.9437 0.6560 0.074 Uiso 1 1 calc R . .
H19B H -0.0166 1.0406 0.6008 0.074 Uiso 1 1 calc R . .
H19C H 0.0276 1.0484 0.7490 0.074 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
O2 C9 1.342(2) . ?
O2 C18 1.455(2) . ?
O4 C17 1.342(2) . ?
O4 C20 1.458(2) . ?
O1 C9 1.212(3) . ?
C9 C6 1.491(3) . ?
C6 C5 1.387(3) . ?
C6 C7 1.389(3) . ?
C8 C3 1.397(3) . ?
C8 C7 1.400(3) . ?
C8 H8 0.9300 . ?
C14 C13 1.388(3) . ?
C14 C15 1.398(3) . ?
C14 C17 1.492(3) . ?
O3 C17 1.210(3) . ?
C1 N1 1.144(3) . ?
C1 C2 1.447(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C7 H7 0.9300 . ?
C11 C16 1.394(3) . ?
C11 C12 1.414(3) . ?
C11 C10 1.468(3) . ?
C4 C3 1.385(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C21 C20 1.492(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C16 H16 0.9300 . ?
C18 C19 1.504(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C13 C12 1.388(3) . ?
C13 H13 0.9300 . ?
C2 C10 1.335(3) . ?
C2 C3 1.501(3) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 O2 C18 116.67(17) . . ?
C17 O4 C20 115.05(16) . . ?
O1 C9 O2 124.12(18) . . ?
O1 C9 C6 124.14(19) . . ?
O2 C9 C6 111.70(17) . . ?
C5 C6 C7 118.58(19) . . ?
C5 C6 C9 121.66(18) . . ?
C7 C6 C9 119.68(19) . . ?
C3 C8 C7 120.81(19) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C13 C14 C15 119.71(18) . . ?
C13 C14 C17 117.65(18) . . ?
C15 C14 C17 122.64(19) . . ?
N1 C1 C2 173.3(2) . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C16 C11 C12 118.44(19) . . ?
C16 C11 C10 115.8(2) . . ?
C12 C11 C10 125.7(2) . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.24(19) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
O3 C17 O4 123.59(18) . . ?
O3 C17 C14 124.09(19) . . ?
O4 C17 C14 112.31(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C20 C21 107.76(18) . . ?
O4 C20 H20A 110.2 . . ?
C21 C20 H20A 110.2 . . ?
O4 C20 H20B 110.2 . . ?
C21 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C15 C16 C11 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
O2 C18 C19 106.47(18) . . ?
O2 C18 H18A 110.4 . . ?
C19 C18 H18A 110.4 . . ?
O2 C18 H18B 110.4 . . ?
C19 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C10 C2 C1 121.3(2) . . ?
C10 C2 C3 123.3(2) . . ?
C1 C2 C3 115.39(18) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C4 C3 C8 118.31(19) . . ?
C4 C3 C2 119.4(2) . . ?
C8 C3 C2 122.32(19) . . ?
C2 C10 C11 130.6(2) . . ?
C2 C10 H10 114.7 . . ?
C11 C10 H10 114.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C18 O2 C9 O1 -2.3(3) . . . . ?
C18 O2 C9 C6 175.45(17) . . . . ?
O1 C9 C6 C5 164.4(2) . . . . ?
O2 C9 C6 C5 -13.3(3) . . . . ?
O1 C9 C6 C7 -12.3(3) . . . . ?
O2 C9 C6 C7 169.96(18) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C17 C14 C15 C16 -179.72(19) . . . . ?
C5 C6 C7 C8 -2.1(3) . . . . ?
C9 C6 C7 C8 174.64(19) . . . . ?
C3 C8 C7 C6 -0.6(3) . . . . ?
C7 C6 C5 C4 2.6(3) . . . . ?
C9 C6 C5 C4 -174.10(19) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C20 O4 C17 O3 -0.6(3) . . . . ?
C20 O4 C17 C14 -179.99(17) . . . . ?
C13 C14 C17 O3 -2.8(3) . . . . ?
C15 C14 C17 O3 176.8(2) . . . . ?
C13 C14 C17 O4 176.60(18) . . . . ?
C15 C14 C17 O4 -3.7(3) . . . . ?
C17 O4 C20 C21 -166.45(18) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C12 C11 C16 C15 0.5(3) . . . . ?
C10 C11 C16 C15 -178.89(19) . . . . ?
C9 O2 C18 C19 -167.7(2) . . . . ?
C15 C14 C13 C12 -0.2(3) . . . . ?
C17 C14 C13 C12 179.48(19) . . . . ?
N1 C1 C2 C10 167.5(19) . . . . ?
N1 C1 C2 C3 -11(2) . . . . ?
C14 C13 C12 C11 0.6(3) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
C10 C11 C12 C13 178.6(2) . . . . ?
C5 C4 C3 C8 -2.4(3) . . . . ?
C5 C4 C3 C2 178.44(19) . . . . ?
C7 C8 C3 C4 2.9(3) . . . . ?
C7 C8 C3 C2 -178.0(2) . . . . ?
C10 C2 C3 C4 -166.6(2) . . . . ?
C1 C2 C3 C4 11.6(3) . . . . ?
C10 C2 C3 C8 14.4(3) . . . . ?
C1 C2 C3 C8 -167.4(2) . . . . ?
C1 C2 C10 C11 5.7(4) . . . . ?
C3 C2 C10 C11 -176.2(2) . . . . ?
C16 C11 C10 C2 177.0(2) . . . . ?
C12 C11 C10 C2 -2.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.049
