# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_vp_na284-3_3_auto
_database_code_depnum_ccdc_archive 'CCDC 2372877'
loop_
_audit_author_name
_audit_author_address
'Andrey Belyaev'
;University of Eastern Finland
Finland
;
_audit_update_record             
;
2024-07-23 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O2'
_chemical_formula_sum            'C23 H21 N O2'
_chemical_formula_weight         343.41
_chemical_absolute_configuration ad
_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 0.0181 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.55890(10)
_cell_length_b                   9.73360(10)
_cell_length_c                   10.97970(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.6880(10)
_cell_angle_gamma                90
_cell_volume                     892.370(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12523
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      78.2260
_cell_measurement_theta_min      5.2830
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14859
_diffrn_reflns_point_group_measured_fraction_full 0.866
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.829
_diffrn_reflns_theta_min         4.127
_diffrn_ambient_temperature      120.15
_diffrn_detector                 HPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'CMOS Photon 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  24.00   0.50    0.10    --  -51.83  19.00-180.00   56
  2  ω     -2.00  24.00   0.50    0.10    --  -51.83  19.00 -90.00   52
  3  ω     -1.00  25.00   0.50    0.10    --  -51.83  19.00 -60.00   52
  4  ω    -50.00 -13.00   0.50    0.10    --  -87.67  57.00  30.00   74
  5  ω    -53.00 -13.00   0.50    0.10    --  -87.67  57.00 120.00   80
  6  ω    -54.00  -4.00   0.50    0.10    --  -51.83 106.00  13.00  100
  7  ω    -89.00 -63.00   0.50    0.10    --  -87.67 106.00  13.00   52
  8  ω     38.00 112.00   0.50    0.10    --   52.33  77.00  60.00  148
  9  ω     98.00 129.00   0.50    0.10    --  102.07  38.00 -30.00   62
 10  ω     88.00 176.00   0.50    0.10    --  102.07  38.00 -60.00  176
 11  ω    124.00 154.00   0.50    0.10    --  107.25  19.00   1.64   60
 12  ω     69.00 107.00   0.50    0.10    --  107.25  19.00   1.64   76
 13  ω     69.00  97.00   0.50    0.10    --  107.25  17.00 169.51   56
 14  ω     80.00 133.00   0.50    0.10    --  107.25  18.00  38.92  106
 15  ω    137.00 163.00   0.50    0.10    --  107.25  15.00 -55.63   52
 16  ω     85.00 148.00   0.50    0.10    --  102.07  57.00-120.00  126
 17  ω     63.00 130.00   0.50    0.10    --  102.07  19.00-120.00  134
 18  ω     70.00 137.00   0.50    0.10    --  107.25  13.00 114.83  134
 19  ω     82.00 107.00   0.50    0.10    --  107.25   3.00  77.38   50
 20  ω    138.00 163.00   0.50    0.10    --  107.25   3.00  77.38   50
 21  ω     76.00 102.00   0.50    0.10    --  107.25  15.00 -55.63   52
 22  ω     57.00  82.00   0.50    0.10    --  107.25  11.00 -59.41   50
 23  ω   -139.00-114.00   0.50    0.10    --  -87.67-106.00 -86.00   50
 24  ω     41.00  68.00   0.50    0.10    --  107.25   3.00  77.38   54
 25  ω    -24.00  29.00   0.50    0.10    --   52.33 -19.00 120.00  106
 26  ω     41.00  91.00   0.50    0.10    --  107.25 -72.00  94.63  100
 27  ω     41.00  77.00   0.50    0.10    --  107.25 -79.00  81.54   72
 28  ω     41.00  67.00   0.50    0.10    --  107.25 -79.00  26.63   52
 29  ω     53.00  79.00   0.50    0.10    --  107.25 -71.00 -85.12   52
 30  ω     41.00  73.00   0.50    0.10    --  107.25 -77.00-122.00   64
 31  ω     40.00  83.00   0.50    0.10    --  107.25 -70.00-167.75   86
 32  ω     26.00  51.00   0.50    0.10    --  102.07 -38.00 -60.00   50
 33  ω     43.00 103.00   0.50    0.10    --  107.25 -70.00 -54.33  120
 34  ω     28.00  53.00   0.50    0.10    --  102.07 -57.00  60.00   50
 35  ω     26.00  51.00   0.50    0.10    --  102.07 -38.00 150.00   50
 36  ω     96.00 122.00   0.50    0.10    --  102.07 106.00  13.00   52
 37  ω     43.00  96.00   0.50    0.10    --  107.25 -81.00  13.32  106
 38  ω     72.00 105.00   0.50    0.10    --  102.07 -99.00  30.00   66
 39  ω     43.00  68.00   0.50    0.10    --  102.07 -99.00  30.00   50
 40  ω      6.00  80.00   0.50    0.10    --   52.33-106.00 -86.00  148
 41  ω     82.00 107.00   0.50    0.10    --  102.07-106.00 -86.00   50
 42  ω     72.00 105.00   0.50    0.10    --  102.07 -99.00 -90.00   66
 43  ω     76.00 105.00   0.50    0.10    --  102.07 -99.00-180.00   58
 44  ω     41.00  72.00   0.50    0.10    --  102.07 -99.00-180.00   62
 45  ω     39.00  66.00   0.50    0.10    --  102.07 -99.00 -90.00   54
 46  ω     41.00  67.00   0.50    0.10    --  107.25 -87.00-178.57   52
 47  ω     81.00 106.00   0.50    0.10    --  102.07 -99.00 -60.00   50
 48  ω     41.00  79.00   0.50    0.10    --  107.25 -88.00 128.36   76
 49  ω     41.00  74.00   0.50    0.10    --  102.07 -99.00 150.00   66
 50  ω    101.00 127.00   0.50    0.10    --  107.25 -88.00 138.70   52
 51  ω     41.00 102.00   0.50    0.10    --  107.25 -85.00  51.41  122
 52  ω     47.00  73.00   0.50    0.10    --  107.25 -85.00  66.68   52
 53  ω     96.00 133.00   0.50    0.10    --  107.25 -85.00  66.68   74
 54  ω     43.00  89.00   0.50    0.10    --  107.25 -84.00 155.91   92
 55  ω     89.00 115.00   0.50    0.10    --  107.25 -86.00 -82.62   52
 56  ω     47.00  73.00   0.50    0.10    --  107.25 -86.00 -82.62   52
 57  ω     48.00  85.00   0.50    0.10    --  107.25 -84.00-146.83   74
 58  ω    103.00 128.00   0.50    0.10    --  107.25 -87.00-178.57   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.610
_reflns_Friedel_fraction_full    0.716
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                3228
_reflns_number_total             3273
_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 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.025
_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)+(0.0390P)²+0.1187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0665
_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:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
C1 C 0.35682(15) 0.70939(15) 0.64464(12) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.331467 0.759028 0.717679 0.023 Uiso 1 1 calc R U . . .
C2 C 0.52085(16) 0.75894(16) 0.62811(12) 0.0198(3) Uani 1 1 d . . . . .
C3 C 0.63145(16) 0.53139(17) 0.70395(14) 0.0241(3) Uani 1 1 d . . . . .
H3A H 0.728164 0.508642 0.768614 0.029 Uiso 1 1 calc R U . . .
H3B H 0.624126 0.465627 0.634137 0.029 Uiso 1 1 calc R U . . .
C4 C 0.48348(16) 0.51857(16) 0.75865(12) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.496941 0.578402 0.834278 0.024 Uiso 1 1 calc R U . . .
C5 C 0.44734(16) 0.37432(16) 0.79331(13) 0.0216(3) Uani 1 1 d . . . . .
C6 C 0.40228(17) 0.34989(18) 0.90642(13) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.402533 0.423243 0.963537 0.031 Uiso 1 1 calc R U . . .
C7 C 0.35710(19) 0.2188(2) 0.93572(15) 0.0325(4) Uani 1 1 d . . . . .
H7 H 0.324555 0.203308 1.011908 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3595(2) 0.11091(19) 0.85403(18) 0.0356(4) Uani 1 1 d . . . . .
H8 H 0.329741 0.021236 0.874514 0.043 Uiso 1 1 calc R U . . .
C9 C 0.4054(2) 0.13388(19) 0.74232(18) 0.0352(4) Uani 1 1 d . . . . .
H9 H 0.408028 0.059796 0.686481 0.042 Uiso 1 1 calc R U . . .
C10 C 0.44749(18) 0.26522(18) 0.71205(15) 0.0281(3) Uani 1 1 d . . . . .
H10 H 0.476813 0.280600 0.634592 0.034 Uiso 1 1 calc R U . . .
C11 C 0.22784(15) 0.74346(16) 0.53096(13) 0.0204(3) Uani 1 1 d . . . . .
C12 C 0.12308(16) 0.85181(17) 0.53395(14) 0.0228(3) Uani 1 1 d . . . . .
H12 H 0.133220 0.905569 0.607489 0.027 Uiso 1 1 calc R U . . .
C13 C 0.00339(17) 0.88169(17) 0.42946(15) 0.0275(3) Uani 1 1 d . . . . .
H13 H -0.068641 0.955412 0.431770 0.033 Uiso 1 1 calc R U . . .
C14 C -0.01064(18) 0.8038(2) 0.32202(15) 0.0308(3) Uani 1 1 d . . . . .
H14 H -0.092383 0.824193 0.250614 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0943(2) 0.69626(19) 0.31850(15) 0.0312(3) Uani 1 1 d . . . . .
H15 H 0.084910 0.643565 0.244412 0.037 Uiso 1 1 calc R U . . .
C16 C 0.21326(17) 0.66520(17) 0.42283(13) 0.0253(3) Uani 1 1 d . . . . .
H16 H 0.284432 0.590845 0.420486 0.030 Uiso 1 1 calc R U . . .
C17 C 0.80407(16) 0.71368(17) 0.64331(13) 0.0230(3) Uani 1 1 d . . . . .
H17A H 0.792801 0.794366 0.587163 0.028 Uiso 1 1 calc R U . . .
H17B H 0.852241 0.638153 0.603544 0.028 Uiso 1 1 calc R U . . .
C18 C 0.91444(16) 0.74986(16) 0.76668(13) 0.0213(3) Uani 1 1 d . . . . .
C19 C 0.8751(2) 0.8557(2) 0.83940(16) 0.0324(4) Uani 1 1 d . . . . .
H19 H 0.777807 0.904863 0.811956 0.039 Uiso 1 1 calc R U . . .
C20 C 0.9773(2) 0.8901(2) 0.95216(18) 0.0413(4) Uani 1 1 d . . . . .
H20 H 0.949429 0.962291 1.001587 0.050 Uiso 1 1 calc R U . . .
C21 C 1.1200(2) 0.8192(2) 0.99269(15) 0.0349(4) Uani 1 1 d . . . . .
H21 H 1.189507 0.842630 1.069877 0.042 Uiso 1 1 calc R U . . .
C22 C 1.16067(18) 0.71492(19) 0.92087(14) 0.0297(3) Uani 1 1 d . . . . .
H22 H 1.258837 0.666985 0.948037 0.036 Uiso 1 1 calc R U . . .
C23 C 1.05770(17) 0.67951(17) 0.80807(13) 0.0245(3) Uani 1 1 d . . . . .
H23 H 1.085719 0.606806 0.759225 0.029 Uiso 1 1 calc R U . . .
N1 N 0.64485(13) 0.67125(14) 0.65881(11) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.34804(11) 0.56561(11) 0.66679(9) 0.0198(2) Uani 1 1 d . . . . .
O2 O 0.53338(12) 0.87694(11) 0.59144(10) 0.0261(2) Uani 1 1 d . . . . .


_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
C1 H1 1.0000 . ?
C1 C2 1.5325(18) . ?
C1 C11 1.5104(18) . ?
C1 O1 1.4253(17) . ?
C2 N1 1.3458(18) . ?
C2 O2 1.2295(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5213(18) . ?
C3 N1 1.4619(19) . ?
C4 H4 1.0000 . ?
C4 C5 1.505(2) . ?
C4 O1 1.4342(15) . ?
C5 C6 1.399(2) . ?
C5 C10 1.387(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(2) . ?
C11 C16 1.393(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5130(19) . ?
C17 N1 1.4692(17) . ?
C18 C19 1.389(2) . ?
C18 C23 1.391(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.396(2) . ?
C23 H23 0.9500 . ?

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
C2 C1 H1 108.0 . . ?
C11 C1 H1 108.0 . . ?
C11 C1 C2 110.82(11) . . ?
O1 C1 H1 108.0 . . ?
O1 C1 C2 114.41(11) . . ?
O1 C1 C11 107.47(11) . . ?
N1 C2 C1 117.60(13) . . ?
O2 C2 C1 118.74(12) . . ?
O2 C2 N1 123.63(12) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
N1 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
N1 C3 C4 110.14(12) . . ?
C3 C4 H4 109.0 . . ?
C5 C4 C3 114.31(12) . . ?
C5 C4 H4 109.0 . . ?
O1 C4 C3 108.10(11) . . ?
O1 C4 H4 109.0 . . ?
O1 C4 C5 107.25(11) . . ?
C6 C5 C4 119.68(14) . . ?
C10 C5 C4 121.49(13) . . ?
C10 C5 C6 118.70(15) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.39(16) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.10(15) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.91(16) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.96(17) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 120.93(15) . . ?
C5 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C1 120.36(13) . . ?
C12 C11 C16 119.85(13) . . ?
C16 C11 C1 119.78(13) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.10(14) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.91(15) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.12(14) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.25(15) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.76(15) . . ?
C15 C16 H16 120.1 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
N1 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
N1 C17 C18 111.98(11) . . ?
C19 C18 C17 120.30(14) . . ?
C19 C18 C23 119.01(14) . . ?
C23 C18 C17 120.68(14) . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.34(16) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.20(17) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.88(15) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.04(15) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.51(14) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C2 N1 C3 124.01(11) . . ?
C2 N1 C17 119.55(13) . . ?
C3 N1 C17 116.41(12) . . ?
C1 O1 C4 111.63(10) . . ?

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
C1 C2 N1 C3 1.46(19) . . . . ?
C1 C2 N1 C17 179.37(12) . . . . ?
C1 C11 C12 C13 -179.26(13) . . . . ?
C1 C11 C16 C15 179.78(14) . . . . ?
C2 C1 C11 C12 -104.14(14) . . . . ?
C2 C1 C11 C16 76.28(16) . . . . ?
C2 C1 O1 C4 45.95(14) . . . . ?
C3 C4 C5 C6 136.69(13) . . . . ?
C3 C4 C5 C10 -47.54(18) . . . . ?
C3 C4 O1 C1 -67.22(14) . . . . ?
C4 C3 N1 C2 -22.17(19) . . . . ?
C4 C3 N1 C17 159.86(12) . . . . ?
C4 C5 C6 C7 175.26(13) . . . . ?
C4 C5 C10 C9 -176.43(14) . . . . ?
C5 C4 O1 C1 169.07(10) . . . . ?
C5 C6 C7 C8 1.3(2) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C5 1.2(3) . . . . ?
C10 C5 C6 C7 -0.6(2) . . . . ?
C11 C1 C2 N1 -133.92(13) . . . . ?
C11 C1 C2 O2 48.22(17) . . . . ?
C11 C1 O1 C4 169.45(10) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 -0.6(2) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
C17 C18 C19 C20 -179.27(16) . . . . ?
C17 C18 C23 C22 178.79(14) . . . . ?
C18 C17 N1 C2 103.98(15) . . . . ?
C18 C17 N1 C3 -77.96(17) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C18 C23 C22 -0.2(2) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C23 -0.7(3) . . . . ?
C21 C22 C23 C18 0.7(2) . . . . ?
C23 C18 C19 C20 -0.3(3) . . . . ?
N1 C3 C4 C5 172.80(11) . . . . ?
N1 C3 C4 O1 53.47(15) . . . . ?
N1 C17 C18 C19 -60.42(19) . . . . ?
N1 C17 C18 C23 120.64(15) . . . . ?
O1 C1 C2 N1 -12.23(17) . . . . ?
O1 C1 C2 O2 169.90(11) . . . . ?
O1 C1 C11 C12 130.19(13) . . . . ?
O1 C1 C11 C16 -49.39(16) . . . . ?
O1 C4 C5 C6 -103.50(14) . . . . ?
O1 C4 C5 C10 72.27(16) . . . . ?
O2 C2 N1 C3 179.21(13) . . . . ?
O2 C2 N1 C17 -2.9(2) . . . . ?


_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
;
####################################################################### 
# 
# 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_vp_6a_2_auto
_database_code_depnum_ccdc_archive 'CCDC 2372879'
loop_
_audit_author_name
_audit_author_address
'Andrey Belyaev'
;University of Eastern Finland
Finland
;
_audit_update_record             
;
2024-07-23 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-03-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_chemical_oxdiff_usercomment     'colorless plates, etoac'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.39260(10)
_cell_length_b                   9.5816(2)
_cell_length_c                   16.9103(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.234(2)
_cell_angle_gamma                90
_cell_volume                     873.74(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9514
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      77.8820
_cell_measurement_theta_min      5.2800
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13716
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.255
_diffrn_reflns_theta_min         2.613
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  69.00   0.50    0.10    --  102.07-125.00-150.00   52
  2  ω     65.00 105.00   0.50    0.10    --  102.07 -99.00 -30.00   80
  3  ω     65.00  91.00   0.50    0.10    --  102.07-114.00  59.00   52
  4  ω     81.00 106.00   0.50    0.10    --  102.07 -99.00  90.00   50
  5  ω     78.00 104.00   0.50    0.10    --  102.07 -99.00  60.00   52
  6  ω     35.00  65.00   0.50    0.10    --  102.07 -99.00  90.00   60
  7  ω     15.00  97.00   0.50    0.10    --   52.08-114.00  59.00  164
  8  ω     70.00  99.00   0.50    0.10    --  102.07 -99.00 -60.00   58
  9  ω     92.00 117.00   0.50    0.10    --  107.25 -84.00-145.81   50
 10  ω     43.00  77.00   0.50    0.10    --  107.25 -84.00-145.81   68
 11  ω     42.00  67.00   0.50    0.10    --  107.25 -82.00-171.70   50
 12  ω     42.00  67.00   0.50    0.10    --  107.25 -82.00 -56.58   50
 13  ω     45.00  71.00   0.50    0.10    --  107.25 -81.00 -68.56   52
 14  ω     87.00 112.00   0.50    0.10    --  107.25 -81.00 -68.56   50
 15  ω    106.00 136.00   0.50    0.10    --  107.25 -86.00  25.78   60
 16  ω     94.00 120.00   0.50    0.10    --  107.25 -85.00 156.28   52
 17  ω     54.00  82.00   0.50    0.10    --  107.25 -78.00 121.68   56
 18  ω     39.00  64.00   0.50    0.10    --  107.25 -74.00 106.40   50
 19  ω     96.00 121.00   0.50    0.10    --  107.25 -74.00 106.40   50
 20  ω     41.00  87.00   0.50    0.10    --  107.25 -72.00  77.44   92
 21  ω     41.00  67.00   0.50    0.10    --  107.25 -73.00  -3.73   52
 22  ω     67.00  93.00   0.50    0.10    --  107.25 -69.00-139.77   52
 23  ω     42.00  93.00   0.50    0.10    --  107.25 -71.00-122.77  102
 24  ω     45.00  74.00   0.50    0.10    --  102.07 -57.00 -90.00   58
 25  ω     43.00 120.00   0.50    0.10    --  107.25 -76.00 -36.25  154
 26  ω     92.00 117.00   0.50    0.10    --  107.25 -73.00  -3.73   50
 27  ω     42.00  89.00   0.50    0.10    --  107.25 -68.00 128.76   94
 28  ω     26.00  51.00   0.50    0.10    --  102.07 -38.00  90.00   50
 29  ω     37.00  71.00   0.50    0.10    --  102.07 -57.00  30.00   68
 30  ω    -20.00  13.00   0.50    0.10    --   52.08 -19.00 120.00   66
 31  ω     25.00  50.00   0.50    0.10    --  102.07 -38.00   0.00   50
 32  ω     26.00  51.00   0.50    0.10    --  102.07 -38.00 -60.00   50
 33  ω     28.00  53.00   0.50    0.10    --  102.07 -57.00-150.00   50
 34  ω     26.00  51.00   0.50    0.10    --  102.07 -38.00-180.00   50
 35  ω     46.00  96.00   0.50    0.10    --  107.25  13.00-163.63  100
 36  ω     68.00 114.00   0.50    0.10    --  107.25  19.00 -64.14   92
 37  ω     89.00 174.00   0.50    0.10    --  102.07  38.00 -60.00  170
 38  ω    142.00 174.00   0.50    0.10    --  107.25  17.00 -33.14   64
 39  ω    138.00 163.00   0.50    0.10    --  107.25  19.00 -64.14   50
 40  ω    100.00 126.00   0.50    0.10    --  107.25  17.00 -33.14   52
 41  ω    142.00 176.00   0.50    0.10    --  107.25  15.00  19.69   68
 42  ω     88.00 123.00   0.50    0.10    --  102.07  38.00  90.00   70
 43  ω     63.00  91.00   0.50    0.10    --  107.25  13.00  73.52   56
 44  ω     66.00  95.00   0.50    0.10    --  107.25  15.00  19.69   58
 45  ω    140.00 165.00   0.50    0.10    --  107.25  16.00 115.57   50
 46  ω    113.00 176.00   0.50    0.10    --  107.25  13.00  73.52  126
 47  ω    112.00 137.00   0.50    0.10    --  107.25  13.00-163.63   50
 48  ω     29.00 115.00   0.50    0.10    --   52.08  77.00 120.00  172
 49  ω     80.00 124.00   0.50    0.10    --  102.07 125.00 120.00   88
 50  ω     88.00 123.00   0.50    0.10    --  102.07 114.00 150.00   70
 51  ω    127.00 153.00   0.50    0.10    --  102.07 114.00 150.00   52
 52  ω     -1.00  24.00   0.50    0.10    --  -51.83  19.00 120.00   50
 53  ω     -3.00  25.00   0.50    0.10    --  -51.83  19.00  90.00   56
 54  ω     -2.00  25.00   0.50    0.10    --  -51.83  19.00  60.00   54
 55  ω    -52.00 -22.00   0.50    0.10    --  -87.67  57.00 -60.00   60
 56  ω    -48.00 -14.00   0.50    0.10    --  -87.67  57.00 -90.00   68
 57  ω     -1.00  25.00   0.50    0.10    --  -51.83  19.00 -90.00   52
 58  ω   -101.00 -62.00   0.50    0.10    --  -87.67 114.00 150.00   78
 59  ω    -75.00 -50.00   0.50    0.10    --  -51.83 114.00 150.00   50
 60  ω   -131.00 -81.00   0.50    0.10    --  -87.67-114.00  59.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2035890000
_diffrn_orient_matrix_UB_12      -0.1057027000
_diffrn_orient_matrix_UB_13      0.0226388000
_diffrn_orient_matrix_UB_21      0.0853678000
_diffrn_orient_matrix_UB_22      -0.0051162000
_diffrn_orient_matrix_UB_23      -0.0867803000
_diffrn_orient_matrix_UB_31      0.1812460000
_diffrn_orient_matrix_UB_32      0.1210424000
_diffrn_orient_matrix_UB_33      0.0161124000
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                3221
_reflns_number_total             3373
_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 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.066
_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)+(0.0571P)²+0.0492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0894
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
C1 C 0.4452(3) 0.36369(19) 0.78274(11) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.301912 0.329706 0.750337 0.027 Uiso 1 1 calc R U . . .
C2 C 0.6716(3) 0.3759(2) 0.72830(11) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.4783(3) 0.5931(2) 0.69190(12) 0.0248(4) Uani 1 1 d . . . . .
H3 H 0.448588 0.658952 0.650964 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3435(3) 0.5983(2) 0.75742(11) 0.0222(4) Uani 1 1 d . . . . .
C5 C 0.1530(3) 0.7023(2) 0.77659(11) 0.0219(4) Uani 1 1 d . . . . .
C6 C 0.1363(3) 0.8264(2) 0.73294(12) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.252260 0.844239 0.692028 0.032 Uiso 1 1 calc R U . . .
C7 C -0.0474(4) 0.9231(2) 0.74881(13) 0.0295(4) Uani 1 1 d . . . . .
H7 H -0.058762 1.005806 0.718038 0.035 Uiso 1 1 calc R U . . .
C8 C -0.2146(4) 0.9000(2) 0.80928(13) 0.0293(4) Uani 1 1 d . . . . .
H8 H -0.339532 0.967035 0.820358 0.035 Uiso 1 1 calc R U . . .
C9 C -0.1990(3) 0.7786(2) 0.85357(12) 0.0292(4) Uani 1 1 d . . . . .
H9 H -0.312686 0.762734 0.895378 0.035 Uiso 1 1 calc R U . . .
C10 C -0.0171(3) 0.6800(2) 0.83698(12) 0.0251(4) Uani 1 1 d . . . . .
H10 H -0.008932 0.596478 0.867169 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4800(3) 0.2655(2) 0.85079(11) 0.0237(4) Uani 1 1 d . . . . .
C12 C 0.6827(3) 0.2786(2) 0.90165(12) 0.0281(4) Uani 1 1 d . . . . .
H12 H 0.805063 0.347707 0.891743 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7064(4) 0.1916(2) 0.96647(12) 0.0332(5) Uani 1 1 d . . . . .
H13 H 0.844843 0.201339 1.000955 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5296(4) 0.0902(3) 0.98141(13) 0.0353(5) Uani 1 1 d . . . . .
H14 H 0.546431 0.030530 1.025976 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3283(4) 0.0763(2) 0.93108(14) 0.0349(5) Uani 1 1 d . . . . .
H15 H 0.207438 0.006343 0.940847 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3021(3) 0.1642(2) 0.86642(13) 0.0288(4) Uani 1 1 d . . . . .
H16 H 0.161962 0.155122 0.832610 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8533(3) 0.5155(2) 0.62106(11) 0.0284(4) Uani 1 1 d . . . . .
H17A H 0.970274 0.435913 0.620879 0.034 Uiso 1 1 calc R U . . .
H17B H 0.948552 0.600539 0.634806 0.034 Uiso 1 1 calc R U . . .
C18 C 0.7451(3) 0.5326(2) 0.53906(11) 0.0258(4) Uani 1 1 d . . . . .
C19 C 0.8572(4) 0.6237(2) 0.48615(12) 0.0289(4) Uani 1 1 d . . . . .
H19 H 0.998017 0.676192 0.502321 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7650(4) 0.6385(2) 0.40986(13) 0.0345(5) Uani 1 1 d . . . . .
H20 H 0.845518 0.699183 0.373720 0.041 Uiso 1 1 calc R U . . .
C21 C 0.5567(4) 0.5653(2) 0.38618(13) 0.0346(5) Uani 1 1 d . . . . .
H21 H 0.491052 0.577544 0.334423 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4439(4) 0.4737(3) 0.43848(13) 0.0344(5) Uani 1 1 d . . . . .
H22 H 0.301538 0.422558 0.422352 0.041 Uiso 1 1 calc R U . . .
C23 C 0.5385(4) 0.4568(2) 0.51412(12) 0.0311(4) Uani 1 1 d . . . . .
H23 H 0.461869 0.392853 0.549350 0.037 Uiso 1 1 calc R U . . .
N1 N 0.6647(3) 0.49150(18) 0.68202(9) 0.0249(3) Uani 1 1 d . . . . .
O1 O 0.3804(2) 0.49826(14) 0.81513(8) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.8354(2) 0.28768(16) 0.72513(8) 0.0300(3) Uani 1 1 d . . . . .


_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
C1 H1 1.0000 . ?
C1 C2 1.537(3) . ?
C1 C11 1.497(3) . ?
C1 O1 1.444(2) . ?
C2 N1 1.357(3) . ?
C2 O2 1.224(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.329(3) . ?
C3 N1 1.409(2) . ?
C4 C5 1.468(2) . ?
C4 O1 1.382(2) . ?
C5 C6 1.402(3) . ?
C5 C10 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 C16 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.511(3) . ?
C17 N1 1.469(2) . ?
C18 C19 1.390(3) . ?
C18 C23 1.394(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?

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
C2 C1 H1 108.1 . . ?
C11 C1 H1 108.1 . . ?
C11 C1 C2 114.26(15) . . ?
O1 C1 H1 108.1 . . ?
O1 C1 C2 110.70(15) . . ?
O1 C1 C11 107.40(15) . . ?
N1 C2 C1 112.80(15) . . ?
O2 C2 C1 123.30(18) . . ?
O2 C2 N1 123.84(18) . . ?
C4 C3 H3 119.4 . . ?
C4 C3 N1 121.20(17) . . ?
N1 C3 H3 119.4 . . ?
C3 C4 C5 126.56(17) . . ?
C3 C4 O1 119.00(16) . . ?
O1 C4 C5 114.45(15) . . ?
C6 C5 C4 120.19(17) . . ?
C10 C5 C4 121.40(18) . . ?
C10 C5 C6 118.39(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.69(18) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.37(19) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.68(18) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.16(18) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.70(19) . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C1 120.87(18) . . ?
C16 C11 C1 120.02(16) . . ?
C16 C11 C12 119.03(18) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.39(19) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.39(18) . . ?
C15 C16 H16 119.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
N1 C17 H17A 108.9 . . ?
N1 C17 H17B 108.9 . . ?
N1 C17 C18 113.26(15) . . ?
C19 C18 C17 119.43(17) . . ?
C19 C18 C23 118.80(18) . . ?
C23 C18 C17 121.75(18) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.48(19) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(2) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C2 N1 C3 120.90(16) . . ?
C2 N1 C17 121.00(16) . . ?
C3 N1 C17 118.09(16) . . ?
C4 O1 C1 112.71(14) . . ?

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
C1 C2 N1 C3 6.4(2) . . . . ?
C1 C2 N1 C17 -174.63(15) . . . . ?
C1 C11 C12 C13 176.90(18) . . . . ?
C1 C11 C16 C15 -177.56(19) . . . . ?
C2 C1 C11 C12 53.0(2) . . . . ?
C2 C1 C11 C16 -130.40(18) . . . . ?
C2 C1 O1 C4 54.60(18) . . . . ?
C3 C4 C5 C6 -14.5(3) . . . . ?
C3 C4 C5 C10 164.29(19) . . . . ?
C3 C4 O1 C1 -33.7(2) . . . . ?
C4 C3 N1 C2 17.0(3) . . . . ?
C4 C3 N1 C17 -162.06(17) . . . . ?
C4 C5 C6 C7 177.90(17) . . . . ?
C4 C5 C10 C9 -178.96(17) . . . . ?
C5 C4 O1 C1 146.54(15) . . . . ?
C5 C6 C7 C8 1.3(3) . . . . ?
C6 C5 C10 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C5 0.8(3) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C11 C1 C2 N1 -162.15(15) . . . . ?
C11 C1 C2 O2 20.5(3) . . . . ?
C11 C1 O1 C4 179.97(14) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C11 1.1(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C17 C18 C19 C20 178.34(19) . . . . ?
C17 C18 C23 C22 -179.6(2) . . . . ?
C18 C17 N1 C2 122.58(19) . . . . ?
C18 C17 N1 C3 -58.4(2) . . . . ?
C18 C19 C20 C21 1.6(3) . . . . ?
C19 C18 C23 C22 -1.2(3) . . . . ?
C19 C20 C21 C22 -1.8(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C18 1.0(3) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?
N1 C3 C4 C5 176.87(17) . . . . ?
N1 C3 C4 O1 -2.9(3) . . . . ?
N1 C17 C18 C19 145.61(19) . . . . ?
N1 C17 C18 C23 -36.0(3) . . . . ?
O1 C1 C2 N1 -40.8(2) . . . . ?
O1 C1 C2 O2 141.87(18) . . . . ?
O1 C1 C11 C12 -70.2(2) . . . . ?
O1 C1 C11 C16 106.40(19) . . . . ?
O1 C4 C5 C6 165.21(16) . . . . ?
O1 C4 C5 C10 -16.0(2) . . . . ?
O2 C2 N1 C3 -176.28(17) . . . . ?
O2 C2 N1 C17 2.7(3) . . . . ?


_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 2.323
_oxdiff_exptl_absorpt_empirical_full_min 0.530
####################################################################### 
# 
# 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_na281_auto
_database_code_depnum_ccdc_archive 'CCDC 2372878'
loop_
_audit_author_name
_audit_author_address
'Andrey Belyaev'
;University of Eastern Finland
Finland
;
_audit_update_record             
;
2024-07-23 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N O'
_chemical_formula_sum            'C23 H23 N O'
_chemical_formula_weight         329.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c20 h20 n2'
_chemical_oxdiff_usercomment     plate
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.43560(10)
_cell_length_b                   9.11270(10)
_cell_length_c                   11.9169(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.3440(10)
_cell_angle_gamma                90
_cell_volume                     898.17(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15602
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.9800
_cell_measurement_theta_min      3.7510
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18692
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.264
_diffrn_reflns_theta_min         3.783
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     76.00 103.00   0.50    0.50    --   53.18  42.00-126.00   54
  2  ω      3.00  55.00   0.50    0.50    --   53.18 -42.00  80.00  104
  3  ω     97.00 148.00   0.50    0.50    --  101.85  42.00-126.00  102
  4  ω     36.00 107.00   0.50    0.50    --  101.85 -42.00  80.00  142
  5  ω    -33.00  -6.00   0.50    0.50    --    6.00 115.00 -65.77   54
  6  ω    -11.00  25.00   0.50    0.50    --   18.00  98.00 123.14   72
  7  ω     -2.00  23.00   0.50    0.50    --   26.00  97.00  46.41   50
  8  ω      7.00  32.00   0.50    0.50    --   34.00  94.00 -58.10   50
  9  ω     15.00  40.00   0.50    0.50    --   38.00  88.00  71.78   50
 10  ω     31.00  56.00   0.50    0.50    --   46.00  76.00 -48.08   50
 11  ω     30.00  59.00   0.50    0.50    --   46.00  76.00-142.77   58
 12  ω     35.00  61.00   0.50    0.50    --   50.00  77.00 127.96   52
 13  ω     36.00  61.00   0.50    0.50    --   52.83  77.00 150.00   50
 14  ω     36.00  61.00   0.50    0.50    --   52.83  77.00 -30.00   50
 15  ω     37.00  62.00   0.50    0.50    --   53.18  77.00   0.00   50
 16  ω     38.00  64.00   0.50    0.50    --   53.18  77.00  30.00   52
 17  ω     -6.00  69.00   0.50    0.50    --   53.18 -77.00  60.00  150
 18  ω     37.00  62.00   0.50    0.50    --   53.18  77.00-120.00   50
 19  ω     34.00  86.00   0.50    0.50    --   53.18-125.00 -90.00  104
 20  ω     72.00  98.00   0.50    0.50    --   53.18-125.00-150.00   52
 21  ω     35.00  68.00   0.50    0.50    --   53.18-125.00-150.00   66
 22  ω     34.00  77.00   0.50    0.50    --   53.18-125.00 -30.00   86
 23  ω     34.00  98.00   0.50    0.50    --   53.18-125.00  30.00  128
 24  ω     86.00 112.00   0.50    0.50    --   53.18  77.00  90.00   52
 25  ω     37.00  63.00   0.50    0.50    --   53.18  77.00  90.00   52
 26  ω     44.00  69.00   0.50    0.50    --   58.00  72.00  58.22   50
 27  ω     48.00  74.00   0.50    0.50    --   62.00  72.00 -82.13   52
 28  ω     49.00  86.00   0.50    0.50    --   62.00  76.00 -29.49   74
 29  ω     49.00  75.00   0.50    0.50    --   62.00  73.00  62.24   52
 30  ω     84.00 109.00   0.50    0.50    --   62.00  67.00-119.68   50
 31  ω     50.00  76.00   0.50    0.50    --   62.00  67.00-119.68   52
 32  ω     98.00 123.00   0.50    0.50    --   62.00  77.00-176.35   50
 33  ω     91.00 124.00   0.50    0.50    --   62.00  76.00 -29.49   66
 34  ω     47.00  81.00   0.50    0.50    --   62.00  77.00-176.35   68
 35  ω     47.00  72.00   0.50    0.50    --   62.00  76.00 168.54   50
 36  ω     52.00 105.00   0.50    0.50    --   66.00  72.00-103.41  106
 37  ω     55.00  92.00   0.50    0.50    --   66.00  70.00  23.75   74
 38  ω    105.00 131.00   0.50    0.50    --   70.00  76.00 106.56   52
 39  ω     54.00  82.00   0.50    0.50    --   70.00  76.00 106.56   56
 40  ω     60.00  86.00   0.50    0.50    --   74.00  72.00  74.54   52
 41  ω     59.00 117.00   0.50    0.50    --   74.00  74.00 -82.75  116
 42  ω     89.00 133.00   0.50    0.50    --   74.00  72.00  74.54   88
 43  ω     72.00  98.00   0.50    0.50    --   78.00  57.00 144.51   52
 44  ω    110.00 147.00   0.50    0.50    --   78.00  54.00  18.09   74
 45  ω     70.00  96.00   0.50    0.50    --   78.00  54.00  18.09   52
 46  ω    115.00 143.00   0.50    0.50    --   78.00  57.00 144.51   56
 47  ω     85.00 135.00   0.50    0.50    --  101.85  77.00  30.00  100
 48  ω     95.00 125.00   0.50    0.50    --  101.85  57.00 -30.00   60
 49  ω     30.00 106.00   0.50    0.50    --  101.85 -37.00 150.00  152
 50  ω    127.00 161.00   0.50    0.50    --  101.85  77.00  90.00   68
 51  ω     85.00 161.00   0.50    0.50    --  101.85  77.00  60.00  152
 52  ω     86.00 159.00   0.50    0.50    --  101.85  77.00-180.00  146
 53  ω     38.00 110.00   0.50    0.50    --  101.85-125.00 120.00  144
 54  ω     85.00 133.00   0.50    0.50    --  101.85  77.00 150.00   96
 55  ω     78.00 103.00   0.50    0.50    --  101.85 -99.00  60.00   50
 56  ω     85.00 123.00   0.50    0.50    --  101.85  77.00  90.00   76
 57  ω     65.00 108.00   0.50    0.50    --  101.85-125.00 -60.00   86
 58  ω     96.00 135.00   0.50    0.50    --  101.85  57.00-120.00   78
 59  ω    110.00 158.00   0.50    0.50    --  101.85 125.00 120.00   96
 60  ω     94.00 153.00   0.50    0.50    --  101.85  57.00 -60.00  118
 61  ω     91.00 161.00   0.50    0.50    --  101.85  77.00 120.00  140
 62  ω     88.00 162.00   0.50    0.50    --  101.85  77.00-120.00  148
 63  ω     44.00 104.00   0.50    0.50    --  101.85 -99.00 -30.00  120
 64  ω     44.00  70.00   0.50    0.50    --  101.85 -99.00  60.00   52
 65  ω     85.00 138.00   0.50    0.50    --  101.85  77.00 -30.00  106
 66  ω     57.00 100.00   0.50    0.50    --  101.85 -99.00-180.00   86
 67  ω     86.00 112.00   0.50    0.50    --  101.85  77.00-150.00   52
 68  ω     85.00 111.00   0.50    0.50    --  101.85  77.00 -90.00   52
 69  ω     85.00 111.00   0.50    0.50    --  101.85  77.00 -60.00   52
 70  ω     85.00 134.00   0.50    0.50    --  101.85  77.00   0.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0064024000
_diffrn_orient_matrix_UB_12      0.1459467000
_diffrn_orient_matrix_UB_13      0.0641704000
_diffrn_orient_matrix_UB_21      -0.1862264000
_diffrn_orient_matrix_UB_22      -0.0060381000
_diffrn_orient_matrix_UB_23      -0.0268603000
_diffrn_orient_matrix_UB_31      0.0022423000
_diffrn_orient_matrix_UB_32      -0.0851569000
_diffrn_orient_matrix_UB_33      0.1119272000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                3593
_reflns_number_total             3675
_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 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_coef       0.0054(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.084
_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)+(0.0257P)²+0.1633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0677
_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:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
C1 C 0.37171(19) 0.73186(17) 0.62420(14) 0.0197(3) Uani 1 1 d . . . . .
H1 H 0.355546 0.798550 0.687634 0.024 Uiso 1 1 calc R U . . .
C2 C 0.54020(19) 0.75713(18) 0.60065(14) 0.0214(3) Uani 1 1 d . . . . .
H2A H 0.560465 0.688808 0.540425 0.026 Uiso 1 1 calc R U . . .
H2B H 0.549449 0.858766 0.573298 0.026 Uiso 1 1 calc R U . . .
C3 C 0.47589(19) 0.55163(17) 0.76312(13) 0.0184(3) Uani 1 1 d . . . . .
H3 H 0.454440 0.617528 0.825560 0.022 Uiso 1 1 calc R U . . .
C4 C 0.64645(19) 0.58114(18) 0.74381(14) 0.0199(3) Uani 1 1 d . . . . .
H4A H 0.725543 0.564349 0.815839 0.024 Uiso 1 1 calc R U . . .
H4B H 0.671828 0.512789 0.685214 0.024 Uiso 1 1 calc R U . . .
C5 C 0.82412(19) 0.76685(19) 0.69183(14) 0.0225(3) Uani 1 1 d . . . . .
H5A H 0.823032 0.858507 0.647084 0.027 Uiso 1 1 calc R U . . .
H5B H 0.864009 0.686832 0.648488 0.027 Uiso 1 1 calc R U . . .
C6 C 0.93738(18) 0.78490(18) 0.80612(13) 0.0206(3) Uani 1 1 d . . . . .
C7 C 1.0878(2) 0.7169(2) 0.82926(15) 0.0242(4) Uani 1 1 d . . . . .
H7 H 1.120904 0.657570 0.772465 0.029 Uiso 1 1 calc R U . . .
C8 C 1.1900(2) 0.7352(2) 0.93481(16) 0.0270(4) Uani 1 1 d . . . . .
H8 H 1.292880 0.688751 0.949369 0.032 Uiso 1 1 calc R U . . .
C9 C 1.1441(2) 0.8199(2) 1.01870(16) 0.0290(4) Uani 1 1 d . . . . .
H9 H 1.213737 0.830152 1.091315 0.035 Uiso 1 1 calc R U . . .
C10 C 0.9955(2) 0.8899(2) 0.99615(18) 0.0352(4) Uani 1 1 d . . . . .
H10 H 0.963364 0.949523 1.053157 0.042 Uiso 1 1 calc R U . . .
C11 C 0.8935(2) 0.8731(2) 0.89041(16) 0.0302(4) Uani 1 1 d . . . . .
H11 H 0.792265 0.922370 0.875329 0.036 Uiso 1 1 calc R U . . .
C12 C 0.23825(18) 0.75921(18) 0.52199(14) 0.0203(3) Uani 1 1 d . . . . .
C13 C 0.1276(2) 0.8719(2) 0.52347(15) 0.0259(4) Uani 1 1 d . . . . .
H13 H 0.136620 0.932832 0.589114 0.031 Uiso 1 1 calc R U . . .
C14 C 0.0035(2) 0.8961(2) 0.42924(16) 0.0312(4) Uani 1 1 d . . . . .
H14 H -0.071273 0.973643 0.430841 0.037 Uiso 1 1 calc R U . . .
C15 C -0.0112(2) 0.8077(2) 0.33350(16) 0.0313(4) Uani 1 1 d . . . . .
H15 H -0.096501 0.823990 0.269687 0.038 Uiso 1 1 calc R U . . .
C16 C 0.0986(2) 0.6953(2) 0.33075(16) 0.0309(4) Uani 1 1 d . . . . .
H16 H 0.089385 0.634834 0.264869 0.037 Uiso 1 1 calc R U . . .
C17 C 0.2228(2) 0.67142(19) 0.42502(16) 0.0257(4) Uani 1 1 d . . . . .
H17 H 0.297795 0.594156 0.422971 0.031 Uiso 1 1 calc R U . . .
C18 C 0.44766(18) 0.39463(18) 0.79504(13) 0.0192(3) Uani 1 1 d . . . . .
C19 C 0.3968(2) 0.3614(2) 0.89585(14) 0.0235(3) Uani 1 1 d . . . . .
H19 H 0.383449 0.437831 0.947376 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3649(2) 0.2163(2) 0.92230(16) 0.0296(4) Uani 1 1 d . . . . .
H20 H 0.329019 0.194936 0.991250 0.036 Uiso 1 1 calc R U . . .
C21 C 0.3852(2) 0.1043(2) 0.84900(17) 0.0329(4) Uani 1 1 d . . . . .
H21 H 0.363327 0.005725 0.866962 0.039 Uiso 1 1 calc R U . . .
C22 C 0.4377(3) 0.1365(2) 0.74901(18) 0.0373(5) Uani 1 1 d . . . . .
H22 H 0.453400 0.059569 0.698514 0.045 Uiso 1 1 calc R U . . .
C23 C 0.4678(2) 0.2809(2) 0.72195(16) 0.0289(4) Uani 1 1 d . . . . .
H23 H 0.502501 0.301860 0.652511 0.035 Uiso 1 1 calc R U . . .
N1 N 0.65894(15) 0.73279(15) 0.70579(12) 0.0199(3) Uani 1 1 d . . . . .
O1 O 0.35832(13) 0.58235(12) 0.66026(9) 0.0191(2) Uani 1 1 d . . . . .


_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
C1 H1 1.0000 . ?
C1 C2 1.520(2) . ?
C1 C12 1.508(2) . ?
C1 O1 1.4397(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N1 1.459(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.525(2) . ?
C3 C18 1.511(2) . ?
C3 O1 1.4444(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 N1 1.465(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.511(2) . ?
C5 N1 1.469(2) . ?
C6 C7 1.390(2) . ?
C6 C11 1.392(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 C17 1.390(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(2) . ?
C18 C23 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.376(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(3) . ?
C23 H23 0.9500 . ?

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
C2 C1 H1 108.6 . . ?
C12 C1 H1 108.6 . . ?
C12 C1 C2 113.74(13) . . ?
O1 C1 H1 108.6 . . ?
O1 C1 C2 109.25(13) . . ?
O1 C1 C12 107.91(12) . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N1 C2 C1 109.11(13) . . ?
N1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C4 C3 H3 108.7 . . ?
C18 C3 H3 108.7 . . ?
C18 C3 C4 113.89(13) . . ?
O1 C3 H3 108.7 . . ?
O1 C3 C4 110.40(12) . . ?
O1 C3 C18 106.33(12) . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C4 C3 109.90(13) . . ?
N1 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
N1 C5 C6 111.51(13) . . ?
C7 C6 C5 121.40(15) . . ?
C7 C6 C11 118.44(15) . . ?
C11 C6 C5 120.15(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.42(16) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.78(16) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.36(17) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.08(18) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.89(16) . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C1 120.55(15) . . ?
C13 C12 C17 118.83(15) . . ?
C17 C12 C1 120.62(14) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.41(17) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.29(17) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.87(16) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.77(17) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 120.83(16) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C3 121.07(15) . . ?
C23 C18 C3 120.34(15) . . ?
C23 C18 C19 118.56(16) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.57(17) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.33(16) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.40(17) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.34(18) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.79(17) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C2 N1 C4 109.27(12) . . ?
C2 N1 C5 112.14(13) . . ?
C4 N1 C5 111.23(13) . . ?
C1 O1 C3 110.83(11) . . ?

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
C1 C2 N1 C4 60.81(16) . . . . ?
C1 C2 N1 C5 -175.38(13) . . . . ?
C1 C12 C13 C14 -179.43(16) . . . . ?
C1 C12 C17 C16 179.35(16) . . . . ?
C2 C1 C12 C13 -115.59(17) . . . . ?
C2 C1 C12 C17 65.0(2) . . . . ?
C2 C1 O1 C3 59.92(15) . . . . ?
C3 C4 N1 C2 -58.43(16) . . . . ?
C3 C4 N1 C5 177.22(13) . . . . ?
C3 C18 C19 C20 177.45(15) . . . . ?
C3 C18 C23 C22 -178.18(17) . . . . ?
C4 C3 C18 C19 122.65(16) . . . . ?
C4 C3 C18 C23 -59.3(2) . . . . ?
C4 C3 O1 C1 -57.74(16) . . . . ?
C5 C6 C7 C8 179.91(16) . . . . ?
C5 C6 C11 C10 179.49(18) . . . . ?
C6 C5 N1 C2 163.20(13) . . . . ?
C6 C5 N1 C4 -74.09(17) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C6 C11 C10 -1.6(3) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C11 C6 C7 C8 1.0(3) . . . . ?
C12 C1 C2 N1 177.98(13) . . . . ?
C12 C1 O1 C3 -175.95(12) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C12 C17 C16 -0.1(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C18 C3 C4 N1 176.15(13) . . . . ?
C18 C3 O1 C1 178.26(12) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C18 C23 C22 0.0(3) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C21 C22 C23 C18 0.8(3) . . . . ?
C23 C18 C19 C20 -0.7(2) . . . . ?
N1 C5 C6 C7 133.02(16) . . . . ?
N1 C5 C6 C11 -48.1(2) . . . . ?
O1 C1 C2 N1 -61.38(16) . . . . ?
O1 C1 C12 C13 123.03(16) . . . . ?
O1 C1 C12 C17 -56.40(19) . . . . ?
O1 C3 C4 N1 56.62(17) . . . . ?
O1 C3 C18 C19 -115.56(16) . . . . ?
O1 C3 C18 C23 62.53(18) . . . . ?


_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 1.571
_oxdiff_exptl_absorpt_empirical_full_min 0.742
