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

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

data_mh-01
_audit_block_doi                 10.5517/ccdc.csd.cc2dnkd1
_database_code_depnum_ccdc_archive 'CCDC 2224293'
loop_
_audit_author_name
_audit_author_address
'Fengya He'
;Anhui University of Chinese Medicine
China
;
_audit_update_record             
;
2022-12-05 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;
_audit_creation_date             2022-01-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1369(7)
_cell_length_b                   11.3965(8)
_cell_length_c                   15.5049(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.344(7)
_cell_angle_gamma                90
_cell_volume                     1772.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1100
_cell_measurement_theta_min      2.2280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             704
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12761
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.675
_diffrn_reflns_theta_min         2.226
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 107.00   0.50    4.58    --   24.18  22.00 -51.00  314
  2  ω     43.00 106.00   0.50    4.58    --   24.18 178.00  90.00  126
  3  ω     49.00 103.00   0.50    4.58    --   24.18 178.00 150.00  108
  4  ω     42.00 106.00   0.50    4.58    --   24.18 178.00 -60.00  128
  5  ω    -48.00 -23.00   0.50    4.58    --   24.18 -22.00 142.00   50
  6  ω   -110.00 -84.00   0.50    4.58    --  -23.24 -22.00 142.00   52
  7  ω    -17.00   8.00   0.50    4.58    --  -23.24 -99.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0343104000
_diffrn_orient_matrix_UB_12      0.0124797000
_diffrn_orient_matrix_UB_13      -0.0356724000
_diffrn_orient_matrix_UB_21      -0.0614839000
_diffrn_orient_matrix_UB_22      0.0125623000
_diffrn_orient_matrix_UB_23      -0.0263589000
_diffrn_orient_matrix_UB_31      0.0057695000
_diffrn_orient_matrix_UB_32      0.0597508000
_diffrn_orient_matrix_UB_33      0.0130035000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3140
_reflns_number_total             4376
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.072
_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)+(0.0694P)²+0.2161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1496
_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.a Ternary CH refined with riding coordinates:
 C12(H12), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C15(H15), C10(H10), C9(H9), C16(H16), C18(H18), C17(H17), C3(H3),
 C5(H5), C2(H2), C1(H1), C4(H4)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.48031(11) 0.53717(9) 0.88753(7) 0.0506(3) Uani 1 1 d . . . . .
O3 O 0.38450(12) 0.54532(11) 0.74887(7) 0.0632(4) Uani 1 1 d . . . . .
N1 N 0.63953(12) 0.82774(10) 0.71174(8) 0.0415(3) Uani 1 1 d . . . . .
O1 O 0.73652(14) 1.00739(11) 0.73062(10) 0.0748(4) Uani 1 1 d . . . . .
C14 C 0.58674(13) 0.75670(11) 0.89239(8) 0.0344(3) Uani 1 1 d . . . . .
C13 C 0.50535(13) 0.71122(12) 0.81148(8) 0.0360(3) Uani 1 1 d . . . . .
C12 C 0.53387(14) 0.74870(12) 0.72135(9) 0.0383(3) Uani 1 1 d . . . . .
H12 H 0.517478 0.688196 0.676150 0.046 Uiso 1 1 calc R U . . .
C20 C 0.45021(14) 0.59018(13) 0.81148(9) 0.0416(3) Uani 1 1 d . . . . .
C11 C 0.41227(14) 0.79582(14) 0.75226(9) 0.0437(3) Uani 1 1 d . . . . .
H11 H 0.326944 0.763247 0.724789 0.052 Uiso 1 1 calc R U . . .
C19 C 0.52810(16) 0.81974(13) 0.95286(9) 0.0466(4) Uani 1 1 d . . . . .
H19 H 0.437028 0.834889 0.942500 0.056 Uiso 1 1 calc R U . . .
C15 C 0.72214(15) 0.73316(14) 0.90942(10) 0.0459(4) Uani 1 1 d . . . . .
H15 H 0.763231 0.690603 0.869587 0.055 Uiso 1 1 calc R U . . .
C8 C 0.64093(17) 0.94253(13) 0.73650(10) 0.0496(4) Uani 1 1 d . . . . .
C7 C 0.74901(16) 0.77945(14) 0.67068(10) 0.0492(4) Uani 1 1 d . . . . .
H7A H 0.774527 0.703595 0.696182 0.059 Uiso 1 1 calc R U . . .
H7B H 0.825627 0.831121 0.681858 0.059 Uiso 1 1 calc R U . . .
C10 C 0.41393(17) 0.92198(15) 0.77205(10) 0.0522(4) Uani 1 1 d . . . . .
H10 H 0.338380 0.956840 0.788399 0.063 Uiso 1 1 calc R U . . .
C9 C 0.52038(18) 0.98674(14) 0.76709(11) 0.0539(4) Uani 1 1 d . . . . .
H9 H 0.518718 1.064958 0.784000 0.065 Uiso 1 1 calc R U . . .
C6 C 0.70925(16) 0.76580(14) 0.57352(11) 0.0498(4) Uani 1 1 d . . . . .
C16 C 0.79604(17) 0.77311(16) 0.98580(12) 0.0595(5) Uani 1 1 d . . . . .
H16 H 0.886629 0.756229 0.997499 0.071 Uiso 1 1 calc R U . . .
C18 C 0.6030(2) 0.86058(14) 1.02853(10) 0.0591(5) Uani 1 1 d . . . . .
H18 H 0.562576 0.903599 1.068438 0.071 Uiso 1 1 calc R U . . .
C17 C 0.7367(2) 0.83756(15) 1.04455(11) 0.0605(5) Uani 1 1 d . . . . .
H17 H 0.787524 0.865480 1.095168 0.073 Uiso 1 1 calc R U . . .
C21 C 0.4269(2) 0.42049(15) 0.89448(12) 0.0638(5) Uani 1 1 d . . . . .
H21A H 0.447102 0.373321 0.846801 0.096 Uiso 1 1 calc R U . . .
H21B H 0.331946 0.425015 0.892711 0.096 Uiso 1 1 calc R U . . .
H21C H 0.466069 0.385660 0.948551 0.096 Uiso 1 1 calc R U . . .
C3 C 0.68676(18) 0.65688(17) 0.53564(13) 0.0655(5) Uani 1 1 d . . . . .
H3 H 0.699832 0.589875 0.570053 0.079 Uiso 1 1 calc R U . . .
C5 C 0.6921(2) 0.86375(19) 0.52030(13) 0.0736(6) Uani 1 1 d . . . . .
H5 H 0.708453 0.937966 0.544444 0.088 Uiso 1 1 calc R U . . .
C2 C 0.6449(2) 0.6460(2) 0.44680(16) 0.0874(7) Uani 1 1 d . . . . .
H2 H 0.628448 0.572185 0.422034 0.105 Uiso 1 1 calc R U . . .
C1 C 0.6278(3) 0.7443(3) 0.39569(16) 0.0949(8) Uani 1 1 d . . . . .
H1 H 0.600137 0.737376 0.336045 0.114 Uiso 1 1 calc R U . . .
C4 C 0.6514(3) 0.8527(3) 0.43234(15) 0.0963(8) Uani 1 1 d . . . . .
H4 H 0.639788 0.919356 0.397475 0.116 Uiso 1 1 calc R U . . .


_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 C20 1.3206(17) . ?
O2 C21 1.4458(18) . ?
O3 C20 1.2081(17) . ?
N1 C12 1.4238(17) . ?
N1 C8 1.363(2) . ?
N1 C7 1.465(2) . ?
O1 C8 1.2326(19) . ?
C14 C13 1.4909(18) . ?
C14 C19 1.382(2) . ?
C14 C15 1.386(2) . ?
C13 C12 1.5284(18) . ?
C13 C20 1.4884(19) . ?
C13 C11 1.5529(19) . ?
C12 H12 0.9800 . ?
C12 C11 1.486(2) . ?
C11 H11 0.9800 . ?
C11 C10 1.470(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.383(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(2) . ?
C8 C9 1.463(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.510(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.319(2) . ?
C9 H9 0.9300 . ?
C6 C3 1.378(2) . ?
C6 C5 1.384(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.368(3) . ?
C17 H17 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.369(4) . ?
C1 H1 0.9300 . ?
C1 C4 1.366(4) . ?
C4 H4 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
C20 O2 C21 116.54(12) . . ?
C12 N1 C7 115.90(12) . . ?
C8 N1 C12 123.71(13) . . ?
C8 N1 C7 120.37(13) . . ?
C19 C14 C13 120.76(12) . . ?
C19 C14 C15 118.88(13) . . ?
C15 C14 C13 120.32(12) . . ?
C14 C13 C12 121.15(11) . . ?
C14 C13 C11 119.76(12) . . ?
C12 C13 C11 57.67(9) . . ?
C20 C13 C14 118.96(11) . . ?
C20 C13 C12 112.32(11) . . ?
C20 C13 C11 112.30(11) . . ?
N1 C12 C13 121.16(11) . . ?
N1 C12 H12 115.0 . . ?
N1 C12 C11 118.48(12) . . ?
C13 C12 H12 115.0 . . ?
C11 C12 C13 61.99(9) . . ?
C11 C12 H12 115.0 . . ?
O2 C20 C13 112.70(11) . . ?
O3 C20 O2 123.56(13) . . ?
O3 C20 C13 123.74(13) . . ?
C13 C11 H11 116.4 . . ?
C12 C11 C13 60.34(9) . . ?
C12 C11 H11 116.4 . . ?
C10 C11 C13 119.76(12) . . ?
C10 C11 C12 115.84(13) . . ?
C10 C11 H11 116.4 . . ?
C14 C19 H19 119.6 . . ?
C14 C19 C18 120.89(15) . . ?
C18 C19 H19 119.6 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.85(15) . . ?
C16 C15 H15 120.1 . . ?
N1 C8 C9 116.54(14) . . ?
O1 C8 N1 122.07(16) . . ?
O1 C8 C9 121.34(15) . . ?
N1 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
N1 C7 C6 111.28(13) . . ?
H7A C7 H7B 108.0 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C11 C10 H10 119.3 . . ?
C9 C10 C11 121.33(15) . . ?
C9 C10 H10 119.3 . . ?
C8 C9 H9 118.1 . . ?
C10 C9 C8 123.72(15) . . ?
C10 C9 H9 118.1 . . ?
C3 C6 C7 121.45(15) . . ?
C3 C6 C5 118.27(18) . . ?
C5 C6 C7 120.27(16) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.58(16) . . ?
C17 C16 H16 119.7 . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.83(16) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.96(15) . . ?
C18 C17 H17 120.0 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C6 C3 H3 119.6 . . ?
C6 C3 C2 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C3 C2 H2 120.1 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C2 C1 H1 120.0 . . ?
C4 C1 C2 120.0(2) . . ?
C4 C1 H1 120.0 . . ?
C5 C4 H4 119.8 . . ?
C1 C4 C5 120.4(2) . . ?
C1 C4 H4 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C12 C11 C13 -112.23(13) . . . . ?
N1 C12 C11 C10 -1.20(18) . . . . ?
N1 C8 C9 C10 0.4(2) . . . . ?
N1 C7 C6 C3 -107.99(17) . . . . ?
N1 C7 C6 C5 70.8(2) . . . . ?
O1 C8 C9 C10 177.85(16) . . . . ?
C14 C13 C12 N1 0.3(2) . . . . ?
C14 C13 C12 C11 -107.69(14) . . . . ?
C14 C13 C20 O2 1.17(19) . . . . ?
C14 C13 C20 O3 -179.15(14) . . . . ?
C14 C13 C11 C12 110.07(13) . . . . ?
C14 C13 C11 C10 5.5(2) . . . . ?
C14 C19 C18 C17 -0.7(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C13 C14 C19 C18 179.07(13) . . . . ?
C13 C14 C15 C16 -178.28(14) . . . . ?
C13 C12 C11 C10 111.03(13) . . . . ?
C13 C11 C10 C9 65.4(2) . . . . ?
C12 N1 C8 O1 176.91(14) . . . . ?
C12 N1 C8 C9 -5.7(2) . . . . ?
C12 N1 C7 C6 75.12(16) . . . . ?
C12 C13 C20 O2 151.19(12) . . . . ?
C12 C13 C20 O3 -29.1(2) . . . . ?
C12 C13 C11 C10 -104.61(16) . . . . ?
C12 C11 C10 C9 -3.7(2) . . . . ?
C20 C13 C12 N1 -148.93(13) . . . . ?
C20 C13 C12 C11 103.04(13) . . . . ?
C20 C13 C11 C12 -103.07(13) . . . . ?
C20 C13 C11 C10 152.31(14) . . . . ?
C11 C13 C12 N1 108.03(15) . . . . ?
C11 C13 C20 O2 -145.97(13) . . . . ?
C11 C13 C20 O3 33.7(2) . . . . ?
C11 C10 C9 C8 4.2(2) . . . . ?
C19 C14 C13 C12 119.97(15) . . . . ?
C19 C14 C13 C20 -92.72(17) . . . . ?
C19 C14 C13 C11 51.95(18) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C19 C18 C17 C16 -0.5(3) . . . . ?
C15 C14 C13 C12 -62.04(18) . . . . ?
C15 C14 C13 C20 85.27(17) . . . . ?
C15 C14 C13 C11 -130.06(14) . . . . ?
C15 C14 C19 C18 1.1(2) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C8 N1 C12 C13 -66.75(18) . . . . ?
C8 N1 C12 C11 6.0(2) . . . . ?
C8 N1 C7 C6 -103.43(16) . . . . ?
C7 N1 C12 C13 114.75(15) . . . . ?
C7 N1 C12 C11 -172.49(12) . . . . ?
C7 N1 C8 O1 -4.7(2) . . . . ?
C7 N1 C8 C9 172.77(13) . . . . ?
C7 C6 C3 C2 177.28(17) . . . . ?
C7 C6 C5 C4 -177.65(19) . . . . ?
C6 C3 C2 C1 1.1(3) . . . . ?
C6 C5 C4 C1 -0.4(4) . . . . ?
C21 O2 C20 O3 -1.8(2) . . . . ?
C21 O2 C20 C13 177.90(13) . . . . ?
C3 C6 C5 C4 1.2(3) . . . . ?
C3 C2 C1 C4 -0.3(4) . . . . ?
C5 C6 C3 C2 -1.6(3) . . . . ?
C2 C1 C4 C5 0.0(4) . . . . ?

_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 1.837
_oxdiff_exptl_absorpt_empirical_full_min 0.309
####################################################################### 
# 
# 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_237
_audit_block_doi                 10.5517/ccdc.csd.cc2dyrx1
_database_code_depnum_ccdc_archive 'CCDC 2233144'
loop_
_audit_author_name
_audit_author_address
'Fengya He'
;Anhui University of Chinese Medicine
China
;
_audit_update_record             
;
2022-12-28 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;
_audit_creation_date             2022-12-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0203(6)
_cell_length_b                   12.3994(6)
_cell_length_c                   13.7932(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.799(6)
_cell_angle_gamma                90
_cell_volume                     1761.95(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5780
_cell_measurement_theta_min      2.2840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11756
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.663
_diffrn_reflns_theta_min         2.046
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00   3.00   0.50    6.77    --   24.18 -19.00 120.00  130
  2  ω    -65.00   5.00   0.50    6.77    --   24.18 -19.00   0.00  140
  3  ω     26.00  52.00   0.50    6.77    --   24.18-117.00  95.00   52
  4  ω    -66.00   5.00   0.50    6.77    --   24.18 -19.00-180.00  142
  5  ω    -92.00 -32.00   0.50    6.77    --  -23.24 117.00-177.00  120
  6  ω    -89.00 -64.00   0.50    6.77    --  -23.24-161.00 -55.00   50
  7  ω     54.00  79.00   0.50    6.77    --   24.18 161.00 -25.00   50
  8  ω     60.00 105.00   0.50    6.77    --   24.18 178.00  90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454833000
_diffrn_orient_matrix_UB_12      0.0427040000
_diffrn_orient_matrix_UB_13      -0.0170250000
_diffrn_orient_matrix_UB_21      -0.0515258000
_diffrn_orient_matrix_UB_22      -0.0371405000
_diffrn_orient_matrix_UB_23      -0.0080169000
_diffrn_orient_matrix_UB_31      0.0029919000
_diffrn_orient_matrix_UB_32      0.0082582000
_diffrn_orient_matrix_UB_33      0.0517319000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3065
_reflns_number_total             4343
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.055
_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)+(0.1192P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.1920
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C11(H11)
1.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C9(H9), C8(H8), C3(H3), C17(H17), C5(H5), C20(H20), C19(H19),
 C2(H2), C18(H18), C4(H4), C1(H1)
1.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.62464(14) 0.22087(11) 0.61396(10) 0.0651(4) Uani 1 1 d . . . . .
N1 N 0.57911(11) 0.36043(9) 0.27051(9) 0.0391(3) Uani 1 1 d . . . . .
O3 O 0.72696(13) 0.42396(11) 0.20304(11) 0.0682(4) Uani 1 1 d . . . . .
O1 O 0.43721(13) 0.28126(13) 0.50071(11) 0.0718(4) Uani 1 1 d . . . . .
C16 C 0.74021(14) 0.36434(11) 0.50471(11) 0.0381(3) Uani 1 1 d . . . . .
C13 C 0.62915(14) 0.28841(11) 0.45678(11) 0.0372(3) Uani 1 1 d . . . . .
C11 C 0.55142(14) 0.28705(11) 0.34171(11) 0.0379(3) Uani 1 1 d . . . . .
H11 H 0.458995 0.271108 0.324301 0.045 Uiso 1 1 calc R U . . .
C10 C 0.64012(15) 0.19339(11) 0.38724(11) 0.0402(4) Uani 1 1 d . . . . .
C6 C 0.48359(14) 0.44241(12) 0.22635(11) 0.0398(4) Uani 1 1 d . . . . .
C14 C 0.55127(16) 0.26454(12) 0.52444(13) 0.0447(4) Uani 1 1 d . . . . .
C21 C 0.72151(16) 0.47478(12) 0.49384(13) 0.0455(4) Uani 1 1 d . . . . .
H21 H 0.640427 0.501845 0.453911 0.055 Uiso 1 1 calc R U . . .
C7 C 0.69575(15) 0.35642(13) 0.25485(13) 0.0458(4) Uani 1 1 d . . . . .
C9 C 0.75612(16) 0.18932(13) 0.35845(13) 0.0468(4) Uani 1 1 d . . . . .
H9 H 0.814149 0.132465 0.382349 0.056 Uiso 1 1 calc R U . . .
C8 C 0.78049(15) 0.26410(14) 0.29954(13) 0.0487(4) Uani 1 1 d . . . . .
H8 H 0.856664 0.257762 0.285426 0.058 Uiso 1 1 calc R U . . .
C3 C 0.40289(15) 0.47487(13) 0.27895(12) 0.0472(4) Uani 1 1 d . . . . .
H3 H 0.413182 0.445105 0.343276 0.057 Uiso 1 1 calc R U . . .
C12 C 0.58334(17) 0.08504(12) 0.39832(14) 0.0519(4) Uani 1 1 d . . . . .
H12A H 0.642677 0.047472 0.456859 0.078 Uiso 1 1 calc R U . . .
H12B H 0.568909 0.043314 0.336593 0.078 Uiso 1 1 calc R U . . .
H12C H 0.502409 0.095560 0.408527 0.078 Uiso 1 1 calc R U . . .
C17 C 0.86265(16) 0.32591(14) 0.56532(12) 0.0493(4) Uani 1 1 d . . . . .
H17 H 0.876875 0.252008 0.573842 0.059 Uiso 1 1 calc R U . . .
C5 C 0.46558(17) 0.48626(14) 0.12936(13) 0.0516(4) Uani 1 1 d . . . . .
H5 H 0.517200 0.463954 0.092452 0.062 Uiso 1 1 calc R U . . .
C20 C 0.82269(18) 0.54541(14) 0.54198(14) 0.0568(5) Uani 1 1 d . . . . .
H20 H 0.809241 0.619458 0.534324 0.068 Uiso 1 1 calc R U . . .
C19 C 0.94315(18) 0.50579(17) 0.60117(15) 0.0602(5) Uani 1 1 d . . . . .
H19 H 1.011153 0.553009 0.633292 0.072 Uiso 1 1 calc R U . . .
C2 C 0.30740(17) 0.55130(14) 0.23581(15) 0.0561(4) Uani 1 1 d . . . . .
H2 H 0.253359 0.572107 0.271141 0.067 Uiso 1 1 calc R U . . .
C18 C 0.96246(17) 0.39643(17) 0.61256(13) 0.0580(5) Uani 1 1 d . . . . .
H18 H 1.043748 0.369825 0.652583 0.070 Uiso 1 1 calc R U . . .
C4 C 0.36977(18) 0.56368(16) 0.08803(15) 0.0621(5) Uani 1 1 d . . . . .
H4 H 0.358364 0.593498 0.023520 0.075 Uiso 1 1 calc R U . . .
C1 C 0.29163(18) 0.59689(17) 0.14093(15) 0.0628(5) Uani 1 1 d . . . . .
H1 H 0.228798 0.649560 0.113013 0.075 Uiso 1 1 calc R U . . .
C15 C 0.5589(3) 0.19164(19) 0.68422(18) 0.0864(8) Uani 1 1 d . . . . .
H15A H 0.486430 0.145811 0.648956 0.130 Uiso 1 1 calc R U . . .
H15B H 0.528591 0.255686 0.707500 0.130 Uiso 1 1 calc R U . . .
H15C H 0.618099 0.154036 0.742805 0.130 Uiso 1 1 calc R U . . .


_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 C14 1.328(2) . ?
O2 C15 1.447(2) . ?
N1 C11 1.4486(17) . ?
N1 C6 1.4342(18) . ?
N1 C7 1.378(2) . ?
O3 C7 1.2268(19) . ?
O1 C14 1.199(2) . ?
C16 C13 1.499(2) . ?
C16 C21 1.385(2) . ?
C16 C17 1.395(2) . ?
C13 C11 1.513(2) . ?
C13 C10 1.5508(19) . ?
C13 C14 1.505(2) . ?
C11 H11 0.9800 . ?
C11 C10 1.5042(19) . ?
C10 C9 1.468(2) . ?
C10 C12 1.513(2) . ?
C6 C3 1.392(2) . ?
C6 C5 1.392(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.388(2) . ?
C7 C8 1.468(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.322(2) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.384(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.375(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.391(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.379(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.373(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.379(3) . ?
C18 H18 0.9300 . ?
C4 H4 0.9300 . ?
C4 C1 1.375(3) . ?
C1 H1 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C14 O2 C15 116.15(17) . . ?
C6 N1 C11 115.69(11) . . ?
C7 N1 C11 121.10(12) . . ?
C7 N1 C6 122.95(12) . . ?
C21 C16 C13 120.43(13) . . ?
C21 C16 C17 118.54(14) . . ?
C17 C16 C13 120.95(13) . . ?
C16 C13 C11 122.64(11) . . ?
C16 C13 C10 121.28(12) . . ?
C16 C13 C14 113.97(12) . . ?
C11 C13 C10 58.80(9) . . ?
C14 C13 C11 114.42(12) . . ?
C14 C13 C10 114.90(12) . . ?
N1 C11 C13 121.82(11) . . ?
N1 C11 H11 114.3 . . ?
N1 C11 C10 120.39(12) . . ?
C13 C11 H11 114.3 . . ?
C10 C11 C13 61.87(9) . . ?
C10 C11 H11 114.3 . . ?
C11 C10 C13 59.33(9) . . ?
C11 C10 C12 119.81(13) . . ?
C9 C10 C13 117.39(12) . . ?
C9 C10 C11 114.39(12) . . ?
C9 C10 C12 115.34(13) . . ?
C12 C10 C13 119.10(12) . . ?
C3 C6 N1 119.47(13) . . ?
C5 C6 N1 121.19(14) . . ?
C5 C6 C3 119.26(14) . . ?
O2 C14 C13 111.34(14) . . ?
O1 C14 O2 123.89(15) . . ?
O1 C14 C13 124.76(16) . . ?
C16 C21 H21 119.7 . . ?
C16 C21 C20 120.59(16) . . ?
C20 C21 H21 119.7 . . ?
N1 C7 C8 116.88(13) . . ?
O3 C7 N1 122.47(15) . . ?
O3 C7 C8 120.60(14) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 C10 121.92(14) . . ?
C8 C9 H9 119.0 . . ?
C7 C8 H8 117.7 . . ?
C9 C8 C7 124.58(14) . . ?
C9 C8 H8 117.7 . . ?
C6 C3 H3 119.9 . . ?
C2 C3 C6 120.20(15) . . ?
C2 C3 H3 119.9 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.51(16) . . ?
C18 C17 H17 119.7 . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.48(16) . . ?
C4 C5 H5 120.3 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 119.98(17) . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.82(16) . . ?
C18 C19 H19 120.1 . . ?
C3 C2 H2 119.7 . . ?
C1 C2 C3 120.61(17) . . ?
C1 C2 H2 119.7 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.57(17) . . ?
C19 C18 H18 119.7 . . ?
C5 C4 H4 119.4 . . ?
C1 C4 C5 121.12(16) . . ?
C1 C4 H4 119.4 . . ?
C2 C1 H1 120.3 . . ?
C4 C1 C2 119.30(17) . . ?
C4 C1 H1 120.3 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C11 C10 C13 112.31(14) . . . . ?
N1 C11 C10 C9 3.73(19) . . . . ?
N1 C11 C10 C12 -139.52(14) . . . . ?
N1 C6 C3 C2 -177.87(14) . . . . ?
N1 C6 C5 C4 178.41(15) . . . . ?
N1 C7 C8 C9 -4.4(2) . . . . ?
O3 C7 C8 C9 178.14(17) . . . . ?
C16 C13 C11 N1 -0.64(19) . . . . ?
C16 C13 C11 C10 109.44(14) . . . . ?
C16 C13 C10 C11 -111.71(14) . . . . ?
C16 C13 C10 C9 -8.2(2) . . . . ?
C16 C13 C10 C12 138.95(15) . . . . ?
C16 C13 C14 O2 -59.33(17) . . . . ?
C16 C13 C14 O1 121.54(18) . . . . ?
C16 C21 C20 C19 0.1(2) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C13 C16 C21 C20 177.08(14) . . . . ?
C13 C16 C17 C18 -177.22(14) . . . . ?
C13 C11 C10 C9 -108.57(14) . . . . ?
C13 C11 C10 C12 108.18(15) . . . . ?
C13 C10 C9 C8 -65.0(2) . . . . ?
C11 N1 C6 C3 24.75(19) . . . . ?
C11 N1 C6 C5 -151.93(14) . . . . ?
C11 N1 C7 O3 -172.73(15) . . . . ?
C11 N1 C7 C8 9.9(2) . . . . ?
C11 C13 C10 C9 103.50(15) . . . . ?
C11 C13 C10 C12 -109.35(15) . . . . ?
C11 C13 C14 O2 152.45(12) . . . . ?
C11 C13 C14 O1 -26.7(2) . . . . ?
C11 C10 C9 C8 1.7(2) . . . . ?
C10 C13 C11 N1 -110.08(14) . . . . ?
C10 C13 C14 O2 87.07(16) . . . . ?
C10 C13 C14 O1 -92.07(19) . . . . ?
C10 C9 C8 C7 -1.5(3) . . . . ?
C6 N1 C11 C13 -110.32(15) . . . . ?
C6 N1 C11 C10 175.90(12) . . . . ?
C6 N1 C7 O3 1.1(2) . . . . ?
C6 N1 C7 C8 -176.29(14) . . . . ?
C6 C3 C2 C1 -0.6(3) . . . . ?
C6 C5 C4 C1 -0.7(3) . . . . ?
C14 C13 C11 N1 144.51(13) . . . . ?
C14 C13 C11 C10 -105.41(13) . . . . ?
C14 C13 C10 C11 104.58(14) . . . . ?
C14 C13 C10 C9 -151.93(14) . . . . ?
C14 C13 C10 C12 -4.8(2) . . . . ?
C21 C16 C13 C11 58.18(19) . . . . ?
C21 C16 C13 C10 128.87(15) . . . . ?
C21 C16 C13 C14 -87.10(17) . . . . ?
C21 C16 C17 C18 -0.4(2) . . . . ?
C21 C20 C19 C18 -0.2(3) . . . . ?
C7 N1 C11 C13 63.94(18) . . . . ?
C7 N1 C11 C10 -9.8(2) . . . . ?
C7 N1 C6 C3 -149.40(15) . . . . ?
C7 N1 C6 C5 33.9(2) . . . . ?
C3 C6 C5 C4 1.7(2) . . . . ?
C3 C2 C1 C4 1.6(3) . . . . ?
C12 C10 C9 C8 146.62(16) . . . . ?
C17 C16 C13 C11 -125.04(15) . . . . ?
C17 C16 C13 C10 -54.4(2) . . . . ?
C17 C16 C13 C14 89.67(17) . . . . ?
C17 C16 C21 C20 0.2(2) . . . . ?
C5 C6 C3 C2 -1.1(2) . . . . ?
C5 C4 C1 C2 -1.0(3) . . . . ?
C20 C19 C18 C17 0.1(3) . . . . ?
C15 O2 C14 O1 0.8(3) . . . . ?
C15 O2 C14 C13 -178.30(15) . . . . ?

_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 2.906
_oxdiff_exptl_absorpt_empirical_full_min 0.350
