# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_wll142
_database_code_depnum_ccdc_archive 'CCDC 2162995'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2019-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O3'
_chemical_formula_sum            'C21 H20 N2 O3'
_chemical_formula_weight         348.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   22.6978(5)
_cell_length_b                   7.32067(11)
_cell_length_c                   12.3466(3)
_cell_angle_alpha                90
_cell_angle_beta                 121.241(3)
_cell_angle_gamma                90
_cell_volume                     1754.07(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3360
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8710
_cell_measurement_theta_min      4.5490
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6852
_diffrn_reflns_point_group_measured_fraction_full 0.753
_diffrn_reflns_point_group_measured_fraction_max 0.753
_diffrn_reflns_theta_full        67.059
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         6.462
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  -5.00   0.50    2.00    --  -33.50 -77.00 -60.00   74
  2  ω    -83.00 -58.00   0.50    2.00    --  -33.50 -57.00-180.00   50
  3  ω   -101.00 -61.00   0.50    2.00    --  -33.50 -77.00 -60.00   80
  4  ω     61.00  99.00   0.50    2.00    --   36.47 178.00  90.00   76
  5  ω     73.00 110.00   0.50    2.00    --   36.47 178.00  30.00   74
  6  ω     14.00  54.00   0.50    2.00    --   36.47  77.00 150.00   80
  7  ω     63.00 110.00   0.50    2.00    --   36.47 178.00 -60.00   94
  8  ω     55.00 103.00   0.50    2.00    --   36.47  37.00 150.00   96
  9  ω     52.00  77.00   0.50    2.00    --   36.47 -99.00 -30.00   50
 10  ω     -3.00  32.00   0.50    2.00    --   36.47 -99.00 -30.00   70
 11  ω      0.00  69.00   0.50    2.00    --   36.47  19.00 -90.00  138
 12  ω     24.00  58.00   0.50    2.00    --   36.47  37.00 120.00   68
 13  ω     64.00  97.00   0.50    2.00    --   36.47 178.00 -90.00   66
 14  ω    -31.00  49.00   0.50    2.00    --   36.47 -57.00-180.00  160
 15  ω     81.00 106.00   0.50    2.00    --   36.47  77.00 150.00   50
 16  ω     20.00  47.00   0.50    2.00    --   36.47  57.00-120.00   54
 17  ω     75.00 105.00   0.50    2.00    --   36.47  57.00 -90.00   60
 18  ω     -1.00 108.00   0.50    2.00    --   36.47  19.00 120.00  218
 19  ω     37.00  64.00   0.50    2.00    --   36.47  57.00 120.00   54
 20  ω     79.00 106.00   0.50    6.50    --  108.00  77.00  90.00   54
 21  ω     88.00 114.00   0.50    6.50    --  108.00  61.00-180.00   52
 22  ω     78.00 134.00   0.50    6.50    --  108.00 -77.00 -30.00  112
 23  ω     85.00 139.00   0.50    6.50    --  108.00  30.00 120.00  108
 24  ω     39.00  76.00   0.50    6.50    --  108.00 -77.00 -30.00   74
 25  ω     82.00 135.00   0.50    6.50    --  108.00  30.00 150.00  106
 26  ω     82.00 109.00   0.50    6.50    --  108.00  30.00-180.00   54
 27  ω    108.00 176.00   0.50    6.50    --  108.00 111.00 -60.00  136
 28  ω    147.00 174.00   0.50    6.50    --  108.00  61.00-150.00   54
 29  ω     88.00 114.00   0.50    6.50    --  108.00  61.00 150.00   52
 30  ω     62.00 119.00   0.50    6.50    --  108.00 -61.00-150.00  114
 31  ω     89.00 140.00   0.50    6.50    --  108.00  61.00-150.00  102
 32  ω    123.00 176.00   0.50    6.50    --  108.00  77.00 150.00  106
 33  ω     88.00 115.00   0.50    6.50    --  108.00  45.00 150.00   54
 34  ω     79.00 105.00   0.50    6.50    --  108.00  77.00 150.00   52
 35  ω     80.00 106.00   0.50    6.50    --  108.00  77.00 120.00   52
 36  ω     82.00 108.00   0.50    6.50    --  108.00  30.00-150.00   52
 37  ω    122.00 170.00   0.50    6.50    --  108.00  77.00-180.00   96
 38  ω     88.00 135.00   0.50    6.50    --  108.00  45.00  90.00   94
 39  ω    133.00 175.00   0.50    6.50    --  108.00  30.00-120.00   84
 40  ω     79.00 106.00   0.50    6.50    --  108.00  77.00-180.00   54
 41  ω     83.00 111.00   0.50    6.50    --  108.00  30.00-120.00   56
 42  ω     88.00 115.00   0.50    6.50    --  108.00  61.00 120.00   54
 43  ω     89.00 114.00   0.50    6.50    --  108.00  45.00-150.00   50
 44  ω    153.00 178.00   0.50    6.50    --  108.00 102.00 -92.00   50
 45  ω     42.00 110.00   0.50    6.50    --  108.00 -94.00-120.00  136
 46  ω     37.00 133.00   0.50    6.50    --  108.00 -30.00-150.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0614456776
_diffrn_orient_matrix_UB_12      -0.0984463587
_diffrn_orient_matrix_UB_13      0.1118490831
_diffrn_orient_matrix_UB_21      0.0442575144
_diffrn_orient_matrix_UB_22      0.0387640807
_diffrn_orient_matrix_UB_23      -0.0588176485
_diffrn_orient_matrix_UB_31      0.0238120111
_diffrn_orient_matrix_UB_32      0.1818887514
_diffrn_orient_matrix_UB_33      0.0730188282
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.505
_reflns_Friedel_fraction_full    0.506
_reflns_Friedel_fraction_max     0.506
_reflns_number_gt                2272
_reflns_number_total             2357
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.3564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C6(H6A,H6B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42476(12) 0.0441(3) 0.4094(3) 0.0723(7) Uani 1 1 d . . . . .
O2 O 0.50144(13) -0.1547(3) 0.5213(3) 0.0690(7) Uani 1 1 d . . . . .
O3 O 0.47200(15) 0.1496(3) 0.6993(3) 0.0823(9) Uani 1 1 d . . . . .
N1 N 0.56183(12) 0.3510(3) 0.3614(2) 0.0453(5) Uani 1 1 d . . . . .
N2 N 0.48426(12) -0.0065(3) 0.4708(2) 0.0491(6) Uani 1 1 d . . . . .
C1 C 0.50984(14) 0.2396(4) 0.3638(3) 0.0431(6) Uani 1 1 d . . . . .
H1A H 0.4901 0.1565 0.2922 0.052 Uiso 1 1 calc R . . . .
H1B H 0.4732 0.3175 0.3556 0.052 Uiso 1 1 calc R . . . .
C2 C 0.54000(13) 0.1292(3) 0.4870(3) 0.0384(5) Uani 1 1 d . . . . .
C3 C 0.60153(14) 0.0240(4) 0.5063(3) 0.0445(6) Uani 1 1 d . . . . .
H3 H 0.6156 -0.0802 0.5567 0.053 Uiso 1 1 calc R . . . .
C4 C 0.63570(15) 0.0772(4) 0.4527(3) 0.0509(7) Uani 1 1 d . . . . .
H4 H 0.6740 0.0095 0.4686 0.061 Uiso 1 1 calc R . . . .
C5 C 0.61690(17) 0.2400(5) 0.3677(3) 0.0557(7) Uani 1 1 d . . . . .
H5A H 0.6575 0.3158 0.3972 0.067 Uiso 1 1 calc R . . . .
H5B H 0.6027 0.1985 0.2829 0.067 Uiso 1 1 calc R . . . .
C6 C 0.58542(15) 0.5070(4) 0.4488(3) 0.0438(6) Uani 1 1 d . . . . .
H6A H 0.5454 0.5621 0.4444 0.053 Uiso 1 1 calc R . . . .
H6B H 0.6048 0.5969 0.4183 0.053 Uiso 1 1 calc R . . . .
C7 C 0.63814(13) 0.4695(3) 0.5871(2) 0.0392(6) Uani 1 1 d . . . . .
C8 C 0.70118(15) 0.5594(4) 0.6437(3) 0.0485(6) Uani 1 1 d . . . . .
H8 H 0.7091 0.6442 0.5966 0.058 Uiso 1 1 calc R . . . .
C9 C 0.75225(15) 0.5269(4) 0.7673(3) 0.0552(7) Uani 1 1 d . . . . .
H9 H 0.7937 0.5906 0.8031 0.066 Uiso 1 1 calc R . . . .
C10 C 0.74174(15) 0.4000(5) 0.8374(3) 0.0549(7) Uani 1 1 d . . . . .
H10 H 0.7763 0.3749 0.9204 0.066 Uiso 1 1 calc R . . . .
C11 C 0.67874(14) 0.3094(4) 0.7828(3) 0.0461(6) Uani 1 1 d . . . . .
H11 H 0.6716 0.2239 0.8306 0.055 Uiso 1 1 calc R . . . .
C12 C 0.62642(13) 0.3431(3) 0.6591(2) 0.0365(5) Uani 1 1 d . . . . .
C13 C 0.55861(13) 0.2417(3) 0.6086(2) 0.0368(5) Uani 1 1 d . . . . .
H13 H 0.5662 0.1523 0.6737 0.044 Uiso 1 1 calc R . . . .
C14 C 0.50095(14) 0.3701(4) 0.5943(3) 0.0413(6) Uani 1 1 d . . . . .
H14A H 0.5215 0.4856 0.6348 0.050 Uiso 1 1 calc R . . . .
H14B H 0.4696 0.3942 0.5049 0.050 Uiso 1 1 calc R . . . .
C15 C 0.45985(14) 0.2976(4) 0.6495(3) 0.0450(6) Uani 1 1 d . . . . .
C16 C 0.40508(13) 0.4172(4) 0.6438(3) 0.0427(6) Uani 1 1 d . . . . .
C17 C 0.38797(16) 0.5855(4) 0.5829(3) 0.0509(7) Uani 1 1 d . . . . .
H17 H 0.4088 0.6237 0.5389 0.061 Uiso 1 1 calc R . . . .
C18 C 0.33986(18) 0.6968(5) 0.5878(3) 0.0636(9) Uani 1 1 d . . . . .
H18 H 0.3280 0.8087 0.5460 0.076 Uiso 1 1 calc R . . . .
C19 C 0.30965(17) 0.6410(5) 0.6546(4) 0.0638(9) Uani 1 1 d . . . . .
H19 H 0.2779 0.7162 0.6587 0.077 Uiso 1 1 calc R . . . .
C20 C 0.32628(18) 0.4750(5) 0.7149(4) 0.0661(9) Uani 1 1 d . . . . .
H20 H 0.3057 0.4379 0.7596 0.079 Uiso 1 1 calc R . . . .
C21 C 0.37346(16) 0.3636(5) 0.7094(3) 0.0567(8) Uani 1 1 d . . . . .
H21 H 0.3843 0.2510 0.7501 0.068 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 N2 1.214(3) . ?
O2 N2 1.211(3) . ?
O3 C15 1.205(3) . ?
N1 C1 1.447(4) . ?
N1 C5 1.459(4) . ?
N1 C6 1.468(3) . ?
N2 C2 1.538(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.535(4) . ?
C2 C3 1.502(4) . ?
C2 C13 1.566(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.313(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.497(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.517(4) . ?
C7 C8 1.390(4) . ?
C7 C12 1.401(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(4) . ?
C12 C13 1.521(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.545(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.509(3) . ?
C15 C16 1.493(4) . ?
C16 C17 1.389(4) . ?
C16 C21 1.388(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(5) . ?
C21 H21 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
C1 N1 C5 111.7(2) . . ?
C1 N1 C6 114.5(2) . . ?
C5 N1 C6 114.7(2) . . ?
O1 N2 C2 117.3(2) . . ?
O2 N2 O1 123.5(3) . . ?
O2 N2 C2 119.2(2) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.6(2) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N2 C2 C13 105.0(2) . . ?
C1 C2 N2 107.3(2) . . ?
C1 C2 C13 115.7(2) . . ?
C3 C2 N2 108.9(2) . . ?
C3 C2 C1 109.1(2) . . ?
C3 C2 C13 110.6(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 117.9 . . ?
C3 C4 C5 124.2(3) . . ?
C5 C4 H4 117.9 . . ?
N1 C5 C4 113.9(2) . . ?
N1 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 H6A 108.0 . . ?
N1 C6 H6B 108.0 . . ?
N1 C6 C7 117.4(2) . . ?
H6A C6 H6B 107.2 . . ?
C7 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 C12 118.6(3) . . ?
C12 C7 C6 122.3(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 H11 119.1 . . ?
C7 C12 C13 123.2(2) . . ?
C11 C12 C7 118.7(2) . . ?
C11 C12 C13 118.1(2) . . ?
C2 C13 H13 106.2 . . ?
C12 C13 C2 111.22(19) . . ?
C12 C13 H13 106.2 . . ?
C12 C13 C14 111.5(2) . . ?
C14 C13 C2 114.7(2) . . ?
C14 C13 H13 106.2 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 C13 114.8(2) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
O3 C15 C14 121.0(3) . . ?
O3 C15 C16 121.1(3) . . ?
C16 C15 C14 117.9(2) . . ?
C17 C16 C15 122.6(2) . . ?
C21 C16 C15 118.5(3) . . ?
C21 C16 C17 118.8(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C2 C1 -35.0(3) . . . . ?
O1 N2 C2 C3 -152.9(3) . . . . ?
O1 N2 C2 C13 88.6(3) . . . . ?
O2 N2 C2 C1 146.6(3) . . . . ?
O2 N2 C2 C3 28.7(4) . . . . ?
O2 N2 C2 C13 -89.8(3) . . . . ?
O3 C15 C16 C17 -177.5(3) . . . . ?
O3 C15 C16 C21 7.0(5) . . . . ?
N1 C1 C2 N2 -170.8(2) . . . . ?
N1 C1 C2 C3 -53.0(3) . . . . ?
N1 C1 C2 C13 72.4(3) . . . . ?
N1 C6 C7 C8 121.2(3) . . . . ?
N1 C6 C7 C12 -56.9(3) . . . . ?
N2 C2 C3 C4 139.9(3) . . . . ?
N2 C2 C13 C12 163.7(2) . . . . ?
N2 C2 C13 C14 -68.5(3) . . . . ?
C1 N1 C5 C4 -37.5(3) . . . . ?
C1 N1 C6 C7 80.1(3) . . . . ?
C1 C2 C3 C4 23.1(3) . . . . ?
C1 C2 C13 C12 -78.3(3) . . . . ?
C1 C2 C13 C14 49.5(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C2 C13 C14 C15 100.5(3) . . . . ?
C3 C2 C13 C12 46.4(3) . . . . ?
C3 C2 C13 C14 174.1(2) . . . . ?
C3 C4 C5 N1 7.6(4) . . . . ?
C5 N1 C1 C2 61.6(3) . . . . ?
C5 N1 C6 C7 -51.0(3) . . . . ?
C6 N1 C1 C2 -70.9(3) . . . . ?
C6 N1 C5 C4 94.9(3) . . . . ?
C6 C7 C8 C9 -177.6(3) . . . . ?
C6 C7 C12 C11 176.4(2) . . . . ?
C6 C7 C12 C13 -4.1(4) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C7 C12 C13 C2 58.0(3) . . . . ?
C7 C12 C13 C14 -71.5(3) . . . . ?
C8 C7 C12 C11 -1.7(3) . . . . ?
C8 C7 C12 C13 177.8(2) . . . . ?
C8 C9 C10 C11 -1.5(5) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C7 1.2(4) . . . . ?
C10 C11 C12 C13 -178.2(3) . . . . ?
C11 C12 C13 C2 -122.6(2) . . . . ?
C11 C12 C13 C14 107.9(3) . . . . ?
C12 C7 C8 C9 0.6(4) . . . . ?
C12 C13 C14 C15 -131.9(2) . . . . ?
C13 C2 C3 C4 -105.2(3) . . . . ?
C13 C14 C15 O3 -0.6(4) . . . . ?
C13 C14 C15 C16 177.6(2) . . . . ?
C14 C15 C16 C17 4.3(4) . . . . ?
C14 C15 C16 C21 -171.2(3) . . . . ?
C15 C16 C17 C18 -175.7(3) . . . . ?
C15 C16 C21 C20 175.3(3) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C17 C16 C21 C20 -0.4(5) . . . . ?
C17 C18 C19 C20 -0.8(6) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 C20 C21 C16 0.4(6) . . . . ?
C21 C16 C17 C18 -0.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.285
_oxdiff_exptl_absorpt_empirical_full_min 0.893
####################################################################### 
# 
# 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_hd_wql41
_database_code_depnum_ccdc_archive 'CCDC 2162997'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H22 N2 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         350.40
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   10.3484(2)
_cell_length_b                   10.5112(2)
_cell_length_c                   16.0533(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1746.18(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9191
_cell_measurement_theta_min      4.2723
_cell_measurement_theta_max      72.0710
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744

_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11545
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_theta_min         5.03
_diffrn_reflns_theta_max         72.14
_diffrn_reflns_theta_full        72.14
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3392
_reflns_number_gt                3292
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.0989
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_restrained_S_all      0.862
_refine_ls_number_reflns         3392
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1347 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.37(9)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.17472(14) 0.53386(12) 0.48785(7) 0.0186(3) Uani d . . . 1 . .
H H23 0.167572 0.572588 0.533387 0.028 Uiso calc U . R 1 . .
O O2 -0.01075(16) 0.44013(15) 0.25048(10) 0.0312(4) Uani d . . . 1 . .
O O3 0.00287(14) 0.30442(15) 0.35141(10) 0.0307(4) Uani d . . . 1 . .
N N3 0.04919(15) 0.36254(16) 0.29233(10) 0.0197(3) Uani d . . . 1 . .
N N1 0.34865(14) 0.36047(14) 0.15462(9) 0.0147(3) Uani d . . . 1 . .
C C1 0.36245(18) 0.22076(16) 0.14654(11) 0.0158(4) Uani d . . . 1 . .
H H3 0.454825 0.198449 0.153154 0.019 Uiso calc U . R 1 . .
H H1 0.33614 0.19567 0.089569 0.019 Uiso calc U . R 1 . .
C C2 0.22138(18) 0.39750(17) 0.18602(10) 0.0146(4) Uani d . . . 1 . .
H H15 0.154352 0.370578 0.145703 0.018 Uiso calc U . R 1 . .
H H14 0.217435 0.491312 0.190904 0.018 Uiso calc U . R 1 . .
C C3 0.19255(16) 0.33773(16) 0.27118(10) 0.0131(4) Uani d . . . 1 . .
C C4 0.26808(17) 0.39549(16) 0.34605(10) 0.0125(3) Uani d . . . 1 . .
H H6 0.224927 0.362312 0.39738 0.015 Uiso calc U . R 1 . .
C C5 0.25744(17) 0.54191(16) 0.35068(10) 0.0140(3) Uani d . . . 1 . .
H H13 0.324204 0.580452 0.314429 0.017 Uiso calc U . R 1 . .
H H12 0.171747 0.568596 0.329551 0.017 Uiso calc U . R 1 . .
C C6 0.27474(17) 0.59085(16) 0.43961(10) 0.0139(4) Uani d . . . 1 . .
H H11 0.360285 0.561424 0.461248 0.017 Uiso calc U . R 1 . .
C C7 0.26925(17) 0.73498(16) 0.44438(10) 0.0129(3) Uani d . . . 1 . .
C C8 0.16261(17) 0.80167(17) 0.41359(10) 0.0156(4) Uani d . . . 1 . .
H H10 0.096635 0.757453 0.384356 0.019 Uiso calc U . R 1 . .
C C9 0.15247(18) 0.93229(17) 0.42547(11) 0.0179(4) Uani d . . . 1 . .
H H9 0.078988 0.976681 0.405135 0.022 Uiso calc U . R 1 . .
C C10 0.2493(2) 0.99804(17) 0.46694(12) 0.0201(4) Uani d . . . 1 . .
H H2 0.241585 1.087148 0.475467 0.024 Uiso calc U . R 1 . .
C C11 0.45743(18) 0.41965(16) 0.19972(10) 0.0152(4) Uani d . . . 1 . .
H H20 0.436027 0.510248 0.209418 0.018 Uiso calc U . R 1 . .
H H21 0.534411 0.417238 0.163138 0.018 Uiso calc U . R 1 . .
C C21 0.28548(18) 0.14510(17) 0.20766(12) 0.0181(4) Uani d . . . 1 . .
H H16 0.291921 0.055006 0.205502 0.022 Uiso calc U . R 1 . .
C C20 0.20844(18) 0.19618(16) 0.26494(11) 0.0163(4) Uani d . . . 1 . .
H H17 0.162925 0.142375 0.302359 0.02 Uiso calc U . R 1 . .
C C12 0.49361(18) 0.36037(15) 0.28276(10) 0.0132(3) Uani d . . . 1 . .
C C13 0.61918(18) 0.31360(17) 0.29240(12) 0.0171(4) Uani d . . . 1 . .
H H19 0.678574 0.321327 0.247565 0.021 Uiso calc U . R 1 . .
C C14 0.65936(18) 0.25599(17) 0.36606(13) 0.0202(4) Uani d . . . 1 . .
H H4 0.745412 0.225582 0.371408 0.024 Uiso calc U . R 1 . .
C C15 0.57318(19) 0.24330(17) 0.43144(12) 0.0200(4) Uani d . . . 1 . .
H H5 0.599031 0.202625 0.481592 0.024 Uiso calc U . R 1 . .
C C16 0.44868(18) 0.29054(16) 0.42306(11) 0.0164(4) Uani d . . . 1 . .
H H18 0.390516 0.283236 0.468597 0.02 Uiso calc U . R 1 . .
C C17 0.40625(16) 0.34849(16) 0.34972(11) 0.0129(3) Uani d . . . 1 . .
C C18 0.3574(2) 0.93386(18) 0.49596(11) 0.0200(4) Uani d . . . 1 . .
H H7 0.424541 0.978957 0.523447 0.024 Uiso calc U . R 1 . .
C C19 0.36682(18) 0.80260(18) 0.48451(10) 0.0159(4) Uani d . . . 1 . .
H H8 0.440912 0.758706 0.504383 0.019 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.425(2) ?
O1 H23 . 0.84 ?
O2 N3 . 1.225(2) ?
O3 N3 . 1.226(2) ?
N3 C3 . 1.544(2) ?
N1 C2 . 1.463(2) ?
N1 C11 . 1.476(2) ?
N1 C1 . 1.481(2) ?
C1 C21 . 1.493(3) ?
C1 H3 . 0.99 ?
C1 H1 . 0.99 ?
C2 C3 . 1.534(2) ?
C2 H15 . 0.99 ?
C2 H14 . 0.99 ?
C3 C20 . 1.500(2) ?
C3 C4 . 1.557(2) ?
C4 C17 . 1.514(2) ?
C4 C5 . 1.545(2) ?
C4 H6 . 1.0 ?
C5 C6 . 1.528(2) ?
C5 H13 . 0.99 ?
C5 H12 . 0.99 ?
C6 C7 . 1.518(2) ?
C6 H11 . 1.0 ?
C7 C19 . 1.393(2) ?
C7 C8 . 1.398(3) ?
C8 C9 . 1.390(2) ?
C8 H10 . 0.95 ?
C9 C10 . 1.388(3) ?
C9 H9 . 0.95 ?
C10 C18 . 1.386(3) ?
C10 H2 . 0.95 ?
C11 C12 . 1.518(2) ?
C11 H20 . 0.99 ?
C11 H21 . 0.99 ?
C21 C20 . 1.330(3) ?
C21 H16 . 0.95 ?
C20 H17 . 0.95 ?
C12 C13 . 1.398(3) ?
C12 C17 . 1.410(2) ?
C13 C14 . 1.392(3) ?
C13 H19 . 0.95 ?
C14 C15 . 1.384(3) ?
C14 H4 . 0.95 ?
C15 C16 . 1.387(3) ?
C15 H5 . 0.95 ?
C16 C17 . 1.396(2) ?
C16 H18 . 0.95 ?
C18 C19 . 1.395(3) ?
C18 H7 . 0.95 ?
C19 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 H23 . . 109.5 ?
O2 N3 O3 . . 123.92(17) ?
O2 N3 C3 . . 118.57(15) ?
O3 N3 C3 . . 117.50(15) ?
C2 N1 C11 . . 113.92(13) ?
C2 N1 C1 . . 112.38(14) ?
C11 N1 C1 . . 112.79(14) ?
N1 C1 C21 . . 114.78(15) ?
N1 C1 H3 . . 108.6 ?
C21 C1 H3 . . 108.6 ?
N1 C1 H1 . . 108.6 ?
C21 C1 H1 . . 108.6 ?
H3 C1 H1 . . 107.5 ?
N1 C2 C3 . . 111.91(14) ?
N1 C2 H15 . . 109.2 ?
C3 C2 H15 . . 109.2 ?
N1 C2 H14 . . 109.2 ?
C3 C2 H14 . . 109.2 ?
H15 C2 H14 . . 107.9 ?
C20 C3 C2 . . 108.99(14) ?
C20 C3 N3 . . 106.70(14) ?
C2 C3 N3 . . 108.28(13) ?
C20 C3 C4 . . 112.53(14) ?
C2 C3 C4 . . 115.51(14) ?
N3 C3 C4 . . 104.28(13) ?
C17 C4 C5 . . 112.99(14) ?
C17 C4 C3 . . 112.15(14) ?
C5 C4 C3 . . 112.94(13) ?
C17 C4 H6 . . 106.0 ?
C5 C4 H6 . . 106.0 ?
C3 C4 H6 . . 106.0 ?
C6 C5 C4 . . 111.84(13) ?
C6 C5 H13 . . 109.2 ?
C4 C5 H13 . . 109.2 ?
C6 C5 H12 . . 109.2 ?
C4 C5 H12 . . 109.2 ?
H13 C5 H12 . . 107.9 ?
O1 C6 C7 . . 111.40(14) ?
O1 C6 C5 . . 106.33(14) ?
C7 C6 C5 . . 112.26(13) ?
O1 C6 H11 . . 108.9 ?
C7 C6 H11 . . 108.9 ?
C5 C6 H11 . . 108.9 ?
C19 C7 C8 . . 118.68(16) ?
C19 C7 C6 . . 120.37(15) ?
C8 C7 C6 . . 120.82(16) ?
C9 C8 C7 . . 120.43(16) ?
C9 C8 H10 . . 119.8 ?
C7 C8 H10 . . 119.8 ?
C10 C9 C8 . . 120.21(17) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C18 C10 C9 . . 120.09(16) ?
C18 C10 H2 . . 120.0 ?
C9 C10 H2 . . 120.0 ?
N1 C11 C12 . . 116.47(14) ?
N1 C11 H20 . . 108.2 ?
C12 C11 H20 . . 108.2 ?
N1 C11 H21 . . 108.2 ?
C12 C11 H21 . . 108.2 ?
H20 C11 H21 . . 107.3 ?
C20 C21 C1 . . 123.99(16) ?
C20 C21 H16 . . 118.0 ?
C1 C21 H16 . . 118.0 ?
C21 C20 C3 . . 120.80(16) ?
C21 C20 H17 . . 119.6 ?
C3 C20 H17 . . 119.6 ?
C13 C12 C17 . . 118.71(15) ?
C13 C12 C11 . . 118.08(16) ?
C17 C12 C11 . . 123.20(16) ?
C14 C13 C12 . . 121.65(17) ?
C14 C13 H19 . . 119.2 ?
C12 C13 H19 . . 119.2 ?
C15 C14 C13 . . 119.58(17) ?
C15 C14 H4 . . 120.2 ?
C13 C14 H4 . . 120.2 ?
C14 C15 C16 . . 119.37(17) ?
C14 C15 H5 . . 120.3 ?
C16 C15 H5 . . 120.3 ?
C15 C16 C17 . . 122.00(17) ?
C15 C16 H18 . . 119.0 ?
C17 C16 H18 . . 119.0 ?
C16 C17 C12 . . 118.67(16) ?
C16 C17 C4 . . 118.17(15) ?
C12 C17 C4 . . 123.16(15) ?
C10 C18 C19 . . 119.56(17) ?
C10 C18 H7 . . 120.2 ?
C19 C18 H7 . . 120.2 ?
C7 C19 C18 . . 120.98(17) ?
C7 C19 H8 . . 119.5 ?
C18 C19 H8 . . 119.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C21 . . . . -30.3(2) ?
C11 N1 C1 C21 . . . . 100.09(17) ?
C11 N1 C2 C3 . . . . -71.61(18) ?
C1 N1 C2 C3 . . . . 58.25(18) ?
N1 C2 C3 C20 . . . . -54.70(18) ?
N1 C2 C3 N3 . . . . -170.41(13) ?
N1 C2 C3 C4 . . . . 73.13(18) ?
O2 N3 C3 C20 . . . . -130.08(17) ?
O3 N3 C3 C20 . . . . 51.2(2) ?
O2 N3 C3 C2 . . . . -12.9(2) ?
O3 N3 C3 C2 . . . . 168.38(16) ?
O2 N3 C3 C4 . . . . 110.63(17) ?
O3 N3 C3 C4 . . . . -68.10(19) ?
C20 C3 C4 C17 . . . . 48.32(19) ?
C2 C3 C4 C17 . . . . -77.73(18) ?
N3 C3 C4 C17 . . . . 163.57(13) ?
C20 C3 C4 C5 . . . . 177.38(15) ?
C2 C3 C4 C5 . . . . 51.33(19) ?
N3 C3 C4 C5 . . . . -67.36(17) ?
C17 C4 C5 C6 . . . . -77.67(18) ?
C3 C4 C5 C6 . . . . 153.70(14) ?
C4 C5 C6 O1 . . . . -59.99(18) ?
C4 C5 C6 C7 . . . . 177.95(15) ?
O1 C6 C7 C19 . . . . 112.34(17) ?
C5 C6 C7 C19 . . . . -128.53(16) ?
O1 C6 C7 C8 . . . . -63.45(19) ?
C5 C6 C7 C8 . . . . 55.7(2) ?
C19 C7 C8 C9 . . . . -2.2(2) ?
C6 C7 C8 C9 . . . . 173.67(16) ?
C7 C8 C9 C10 . . . . 1.0(3) ?
C8 C9 C10 C18 . . . . 0.7(3) ?
C2 N1 C11 C12 . . . . 79.29(18) ?
C1 N1 C11 C12 . . . . -50.4(2) ?
N1 C1 C21 C20 . . . . 0.8(3) ?
C1 C21 C20 C3 . . . . 0.7(3) ?
C2 C3 C20 C21 . . . . 25.3(2) ?
N3 C3 C20 C21 . . . . 142.06(17) ?
C4 C3 C20 C21 . . . . -104.15(19) ?
N1 C11 C12 C13 . . . . 120.87(17) ?
N1 C11 C12 C17 . . . . -58.0(2) ?
C17 C12 C13 C14 . . . . 0.0(2) ?
C11 C12 C13 C14 . . . . -178.93(16) ?
C12 C13 C14 C15 . . . . 0.6(3) ?
C13 C14 C15 C16 . . . . -1.3(3) ?
C14 C15 C16 C17 . . . . 1.4(3) ?
C15 C16 C17 C12 . . . . -0.8(3) ?
C15 C16 C17 C4 . . . . 179.17(15) ?
C13 C12 C17 C16 . . . . 0.0(2) ?
C11 C12 C17 C16 . . . . 178.96(15) ?
C13 C12 C17 C4 . . . . -179.88(15) ?
C11 C12 C17 C4 . . . . -1.0(2) ?
C5 C4 C17 C16 . . . . 106.62(17) ?
C3 C4 C17 C16 . . . . -124.35(16) ?
C5 C4 C17 C12 . . . . -73.5(2) ?
C3 C4 C17 C12 . . . . 55.6(2) ?
C9 C10 C18 C19 . . . . -1.2(3) ?
C8 C7 C19 C18 . . . . 1.7(2) ?
C6 C7 C19 C18 . . . . -174.18(15) ?
C10 C18 C19 C7 . . . . 0.0(3) ?

####################################################################### 
# 
# 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_hhb36
_database_code_depnum_ccdc_archive 'CCDC 2162996'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2020-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O3'
_chemical_formula_sum            'C22 H22 N2 O3'
_chemical_formula_weight         362.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3385(5)
_cell_length_b                   7.6142(3)
_cell_length_c                   19.6850(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.363(4)
_cell_angle_gamma                90
_cell_volume                     1824.71(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3387
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4460
_cell_measurement_theta_min      5.3280
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13564
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.631
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  23.00   1.00    1.50    --  -33.50  77.00  60.00   26
  2  ω   -103.00 -12.00   1.00    1.50    --  -33.50 -37.00 -90.00   91
  3  ω    -35.00  -9.00   1.00    1.50    --  -33.50  77.00  60.00   26
  4  ω     78.00 103.00   1.00    1.50    --   36.47  77.00 -90.00   25
  5  ω     66.00  92.00   1.00    1.50    --   36.47  37.00  30.00   26
  6  ω     24.00  53.00   1.00    1.50    --   36.47 -37.00 -90.00   29
  7  ω     19.00  83.00   1.00    1.50    --   36.47  57.00  60.00   64
  8  ω     10.00  60.00   1.00    1.50    --   36.47  77.00 -90.00   50
  9  ω    -13.00  14.00   1.00    1.50    --   36.47 -37.00 -90.00   27
 10  ω     64.00 109.00   1.00    1.50    --   36.47 178.00-120.00   45
 11  ω     58.00  87.00   1.00    1.50    --   36.47 178.00-150.00   29
 12  ω     16.00  65.00   1.00    1.50    --   36.47  37.00  30.00   49
 13  ω     58.00 106.00   1.00    1.50    --   36.47 178.00 -60.00   48
 14  ω     -4.00  22.00   1.00    1.50    --   36.47 102.00  64.60   26
 15  ω     23.00  98.00   1.00    1.50    --   36.47  57.00  90.00   75
 16  ω     28.00 105.00   1.00    1.50    --   36.47  57.00-180.00   77
 17  ω     88.00 147.00   1.00    6.00    --  108.00  61.00  30.00   59
 18  ω     76.00 108.00   1.00    6.00    --  108.00 -94.00-180.00   32
 19  ω     40.00 127.00   1.00    6.00    --  108.00 -61.00 120.00   87
 20  ω    139.00 166.00   1.00    6.00    --  108.00  61.00 120.00   27
 21  ω     90.00 116.00   1.00    6.00    --  108.00  45.00 120.00   26
 22  ω     44.00 133.00   1.00    6.00    --  108.00 -30.00-180.00   89
 23  ω     79.00 105.00   1.00    6.00    --  108.00  77.00 150.00   26
 24  ω     90.00 117.00   1.00    6.00    --  108.00  61.00 120.00   27
 25  ω     82.00 108.00   1.00    6.00    --  108.00  30.00-180.00   26
 26  ω     82.00 125.00   1.00    6.00    --  108.00  30.00 120.00   43
 27  ω     84.00 133.00   1.00    6.00    --  108.00  30.00-150.00   49
 28  ω     65.00  93.00   1.00    6.00    --  108.00  15.00-150.00   28
 29  ω     38.00  92.00   1.00    6.00    --  108.00 -94.00   0.00   54
 30  ω     88.00 114.00   1.00    6.00    --  108.00  61.00-180.00   26
 31  ω     38.00  97.00   1.00    6.00    --  108.00 -94.00 120.00   59
 32  ω    126.00 173.00   1.00    6.00    --  108.00  30.00  60.00   47
 33  ω     79.00 105.00   1.00    6.00    --  108.00  77.00 120.00   26
 34  ω     87.00 160.00   1.00    6.00    --  108.00  30.00   0.00   73
 35  ω     88.00 114.00   1.00    6.00    --  108.00  45.00-180.00   26
 36  ω     89.00 115.00   1.00    6.00    --  108.00  61.00 150.00   26
 37  ω     85.00 110.00   1.00    6.00    --  108.00  30.00 150.00   25
 38  ω    137.00 176.00   1.00    6.00    --  108.00  61.00-180.00   39
 39  ω    114.00 174.00   1.00    6.00    --  108.00  77.00 150.00   60
 40  ω     73.00 131.00   1.00    6.00    --  108.00 -77.00-150.00   58
 41  ω     82.00 120.00   1.00    6.00    --  108.00  77.00-150.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0532521000
_diffrn_orient_matrix_UB_12      0.1487839000
_diffrn_orient_matrix_UB_13      0.0470053000
_diffrn_orient_matrix_UB_21      -0.0835345000
_diffrn_orient_matrix_UB_22      -0.0309474000
_diffrn_orient_matrix_UB_23      0.0490366000
_diffrn_orient_matrix_UB_31      0.0787247000
_diffrn_orient_matrix_UB_32      -0.1335110000
_diffrn_orient_matrix_UB_33      0.0409987000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2641
_reflns_number_total             3260
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+0.2745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N2, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C17(H17A,H17B), C21(H21A,H21B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C20(H20)
4.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78211(12) 0.19048(16) 0.49109(6) 0.0610(3) Uani 1 1 d . . . . .
O2 O 0.98031(11) 0.0320(2) 0.68507(8) 0.0788(5) Uani 1 1 d . . . . .
O3 O 0.94712(13) 0.0911(3) 0.78630(8) 0.0877(5) Uani 1 1 d . . . . .
N1 N 0.67664(14) -0.2334(2) 0.69141(8) 0.0627(4) Uani 1 1 d . . . . .
N2 N 0.91635(12) 0.0605(2) 0.72560(8) 0.0585(4) Uani 1 1 d . U . . .
C1 C 0.82801(15) 0.5174(2) 0.43851(9) 0.0530(4) Uani 1 1 d . . . . .
H1 H 0.7958 0.4333 0.4074 0.064 Uiso 1 1 calc R . . . .
C2 C 0.85792(17) 0.6781(3) 0.41495(10) 0.0620(5) Uani 1 1 d . . . . .
H2 H 0.8457 0.7017 0.3680 0.074 Uiso 1 1 calc R . . . .
C3 C 0.90539(16) 0.8028(2) 0.46016(11) 0.0627(5) Uani 1 1 d . . . . .
H3 H 0.9240 0.9118 0.4441 0.075 Uiso 1 1 calc R . . . .
C4 C 0.92557(16) 0.7665(3) 0.52937(11) 0.0628(5) Uani 1 1 d . . . . .
H4 H 0.9592 0.8506 0.5601 0.075 Uiso 1 1 calc R . . . .
C5 C 0.89646(14) 0.6065(2) 0.55373(9) 0.0501(4) Uani 1 1 d . . . . .
H5 H 0.9108 0.5828 0.6007 0.060 Uiso 1 1 calc R . . . .
C6 C 0.84589(12) 0.4810(2) 0.50845(8) 0.0404(3) Uani 1 1 d . . . . .
C7 C 0.81270(12) 0.3061(2) 0.53227(8) 0.0432(3) Uani 1 1 d . . . . .
C8 C 0.82112(13) 0.2747(2) 0.60921(8) 0.0468(4) Uani 1 1 d . . . . .
H8A H 0.7897 0.3740 0.6300 0.056 Uiso 1 1 calc R . . . .
H8B H 0.8979 0.2660 0.6297 0.056 Uiso 1 1 calc R . . . .
C9 C 0.76157(12) 0.1072(2) 0.62465(8) 0.0426(3) Uani 1 1 d . . . . .
H9 H 0.7835 0.0166 0.5943 0.051 Uiso 1 1 calc R . . . .
C10 C 0.63649(12) 0.1230(2) 0.60604(8) 0.0428(3) Uani 1 1 d . . . . .
C11 C 0.58594(15) 0.2840(2) 0.58920(9) 0.0537(4) Uani 1 1 d . . . . .
H11 H 0.6287 0.3850 0.5911 0.064 Uiso 1 1 calc R . . . .
C12 C 0.47316(16) 0.2971(3) 0.56966(10) 0.0672(5) Uani 1 1 d . . . . .
H12 H 0.4411 0.4062 0.5587 0.081 Uiso 1 1 calc R . . . .
C13 C 0.40855(15) 0.1491(4) 0.56637(10) 0.0706(6) Uani 1 1 d . . . . .
H13 H 0.3330 0.1570 0.5526 0.085 Uiso 1 1 calc R . . . .
C14 C 0.45725(15) -0.0104(3) 0.58371(10) 0.0632(5) Uani 1 1 d . . . . .
H14 H 0.4135 -0.1103 0.5819 0.076 Uiso 1 1 calc R . . . .
C15 C 0.56955(14) -0.0266(2) 0.60373(8) 0.0501(4) Uani 1 1 d . . . . .
C16 C 0.61640(17) -0.2072(2) 0.62178(10) 0.0614(5) Uani 1 1 d . . . . .
H16A H 0.5563 -0.2908 0.6146 0.074 Uiso 1 1 calc R . . . .
H16B H 0.6652 -0.2363 0.5895 0.074 Uiso 1 1 calc R . . . .
C17 C 0.78698(16) -0.1686(2) 0.70124(10) 0.0572(4) Uani 1 1 d . . . . .
H17A H 0.8240 -0.2157 0.6654 0.069 Uiso 1 1 calc R . . . .
H17B H 0.8255 -0.2107 0.7451 0.069 Uiso 1 1 calc R . . . .
C18 C 0.79389(13) 0.0350(2) 0.69995(8) 0.0471(4) Uani 1 1 d . U . . .
C19 C 0.72672(14) 0.1114(2) 0.75073(8) 0.0510(4) Uani 1 1 d . . . . .
C20 C 0.64846(16) 0.0123(3) 0.76988(9) 0.0598(5) Uani 1 1 d . . . . .
H20 H 0.6074 0.0618 0.8006 0.072 Uiso 1 1 calc R . . . .
C21 C 0.62008(18) -0.1715(3) 0.74662(11) 0.0702(6) Uani 1 1 d . . . . .
H21A H 0.6377 -0.2497 0.7858 0.084 Uiso 1 1 calc R . . . .
H21B H 0.5415 -0.1784 0.7310 0.084 Uiso 1 1 calc R . . . .
C22 C 0.74218(19) 0.3012(3) 0.77176(11) 0.0704(5) Uani 1 1 d . . . . .
H22A H 0.8189 0.3246 0.7861 0.106 Uiso 1 1 calc GR . . . .
H22B H 0.7032 0.3248 0.8092 0.106 Uiso 1 1 calc GR . . . .
H22C H 0.7143 0.3752 0.7334 0.106 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.215(2) . ?
O2 N2 1.229(2) . ?
O3 N2 1.216(2) . ?
N1 C16 1.463(2) . ?
N1 C17 1.431(3) . ?
N1 C21 1.462(3) . ?
N2 C18 1.526(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C6 C7 1.491(2) . ?
C7 C8 1.520(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.527(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.532(2) . ?
C9 C18 1.570(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.403(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 C16 1.512(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.553(2) . ?
C18 C19 1.514(2) . ?
C19 C20 1.328(3) . ?
C19 C22 1.507(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.496(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C17 N1 C16 114.01(15) . . ?
C17 N1 C21 110.29(16) . . ?
C21 N1 C16 114.92(17) . . ?
O2 N2 C18 117.95(15) . . ?
O3 N2 O2 122.74(16) . . ?
O3 N2 C18 118.92(15) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.20(17) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.45(18) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.75(17) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.51(18) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.12(17) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 118.90(14) . . ?
C5 C6 C1 118.93(15) . . ?
C5 C6 C7 122.14(14) . . ?
O1 C7 C6 120.59(14) . . ?
O1 C7 C8 120.94(15) . . ?
C6 C7 C8 118.44(13) . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C7 C8 C9 111.89(13) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9 106.1 . . ?
C8 C9 C10 112.70(13) . . ?
C8 C9 C18 115.07(13) . . ?
C10 C9 H9 106.1 . . ?
C10 C9 C18 110.14(12) . . ?
C18 C9 H9 106.1 . . ?
C11 C10 C9 121.41(14) . . ?
C11 C10 C15 117.96(15) . . ?
C15 C10 C9 120.60(15) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.38(18) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.13(19) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.09(17) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.80(19) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 C16 122.02(15) . . ?
C14 C15 C10 119.63(18) . . ?
C14 C15 C16 118.35(17) . . ?
N1 C16 C15 117.44(15) . . ?
N1 C16 H16A 107.9 . . ?
N1 C16 H16B 107.9 . . ?
C15 C16 H16A 107.9 . . ?
C15 C16 H16B 107.9 . . ?
H16A C16 H16B 107.2 . . ?
N1 C17 H17A 108.9 . . ?
N1 C17 H17B 108.9 . . ?
N1 C17 C18 113.31(15) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
N2 C18 C9 110.71(12) . . ?
N2 C18 C17 100.10(14) . . ?
C17 C18 C9 111.01(14) . . ?
C19 C18 N2 110.59(13) . . ?
C19 C18 C9 113.98(13) . . ?
C19 C18 C17 109.58(14) . . ?
C20 C19 C18 118.08(17) . . ?
C20 C19 C22 122.17(18) . . ?
C22 C19 C18 119.42(16) . . ?
C19 C20 H20 116.9 . . ?
C19 C20 C21 126.13(18) . . ?
C21 C20 H20 116.9 . . ?
N1 C21 C20 114.39(16) . . ?
N1 C21 H21A 108.7 . . ?
N1 C21 H21B 108.7 . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C7 C8 C9 -14.2(2) . . . . ?
O2 N2 C18 C9 -40.8(2) . . . . ?
O2 N2 C18 C17 76.37(19) . . . . ?
O2 N2 C18 C19 -168.13(17) . . . . ?
O3 N2 C18 C9 146.19(18) . . . . ?
O3 N2 C18 C17 -96.6(2) . . . . ?
O3 N2 C18 C19 18.9(2) . . . . ?
N1 C17 C18 N2 169.21(14) . . . . ?
N1 C17 C18 C9 -73.84(18) . . . . ?
N1 C17 C18 C19 52.94(19) . . . . ?
N2 C18 C19 C20 -130.81(17) . . . . ?
N2 C18 C19 C22 55.7(2) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C6 C7 O1 8.2(2) . . . . ?
C1 C6 C7 C8 -173.44(14) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C7 -179.97(16) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 1.7(2) . . . . ?
C4 C5 C6 C7 -179.92(16) . . . . ?
C5 C6 C7 O1 -170.10(15) . . . . ?
C5 C6 C7 C8 8.2(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C7 C8 C9 167.52(13) . . . . ?
C7 C8 C9 C10 -69.68(17) . . . . ?
C7 C8 C9 C18 162.90(13) . . . . ?
C8 C9 C10 C11 -10.9(2) . . . . ?
C8 C9 C10 C15 167.35(14) . . . . ?
C8 C9 C18 N2 -37.4(2) . . . . ?
C8 C9 C18 C17 -147.67(15) . . . . ?
C8 C9 C18 C19 88.02(17) . . . . ?
C9 C10 C11 C12 177.34(16) . . . . ?
C9 C10 C15 C14 -177.01(15) . . . . ?
C9 C10 C15 C16 2.3(2) . . . . ?
C9 C18 C19 C20 103.70(18) . . . . ?
C9 C18 C19 C22 -69.8(2) . . . . ?
C10 C9 C18 N2 -166.12(13) . . . . ?
C10 C9 C18 C17 83.63(17) . . . . ?
C10 C9 C18 C19 -40.69(19) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C10 C15 C16 N1 60.5(2) . . . . ?
C11 C10 C15 C14 1.3(2) . . . . ?
C11 C10 C15 C16 -179.38(15) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C10 -0.5(3) . . . . ?
C13 C14 C15 C16 -179.86(18) . . . . ?
C14 C15 C16 N1 -120.22(19) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C16 N1 C17 C18 69.7(2) . . . . ?
C16 N1 C21 C20 -93.0(2) . . . . ?
C17 N1 C16 C15 -79.3(2) . . . . ?
C17 N1 C21 C20 37.5(2) . . . . ?
C17 C18 C19 C20 -21.4(2) . . . . ?
C17 C18 C19 C22 165.11(16) . . . . ?
C18 C9 C10 C11 119.05(17) . . . . ?
C18 C9 C10 C15 -62.67(19) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 N1 -8.0(3) . . . . ?
C21 N1 C16 C15 49.4(2) . . . . ?
C21 N1 C17 C18 -61.4(2) . . . . ?
C22 C19 C20 C21 174.09(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.869
